# Electronic Supplementary Material (ESI) for Green Chemistry. # This journal is © The Royal Society of Chemistry 2015 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_2b_14srv257 _database_code_depnum_ccdc_archive 'CCDC 1401917' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2014-11-24 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949) ; _chemical_name_common ? _chemical_name_systematic ; (S)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate ; _chemical_formula_moiety 'C7 H10 F N O3' _chemical_formula_sum 'C7 H10 F N O3' _chemical_formula_weight 175.16 _chemical_absolute_configuration ad _chemical_melting_point '115-116 C' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 8.5224(4) _cell_length_b 10.3050(5) _cell_length_c 9.1442(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.3404(11) _cell_angle_gamma 90.00 _cell_volume 803.06(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8801 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 74.47 _cell_measurement_theta_min 4.29 _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1189 before and 0.0931 after correction. The Ratio of minimum to maximum transmission is 0.8291. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.29 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_unetI/netI 0.0576 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7399 _diffrn_reflns_theta_full 72.46 _diffrn_reflns_theta_max 72.46 _diffrn_reflns_theta_min 4.84 _diffrn_ambient_temperature 120.0 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measurement_device 'Bruker D8 Venture' _diffrn_measurement_device_type D8Venture _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'ImuS microsource' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2829 _reflns_number_total 2833 _reflns_threshold_expression >2sigma(I) _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.244 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 2833 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0547 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1520 _refine_ls_wR_factor_ref 0.1520 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.7533(2) 0.48062(18) 0.3623(2) 0.0362(4) Uani 1 d . . . O1 O 0.8108(3) 0.7298(2) 0.2396(2) 0.0377(5) Uani 1 d . . . O2 O 0.6992(2) 0.7552(2) 0.5858(2) 0.0309(5) Uani 1 d . . . O3 O 0.5292(3) 0.6351(3) 0.4548(3) 0.0516(7) Uani 1 d . . . N1 N 1.0467(3) 0.6772(3) 0.3379(3) 0.0362(6) Uani 1 d . . . C1 C 0.8905(4) 0.6734(3) 0.3319(3) 0.0279(6) Uani 1 d . . . C2 C 0.8069(3) 0.5869(3) 0.4447(3) 0.0299(6) Uani 1 d . . . C3 C 0.9074(4) 0.5363(4) 0.5693(4) 0.0356(7) Uani 1 d . . . C4 C 1.0664(4) 0.4980(4) 0.5137(4) 0.0388(7) Uani 1 d . . . C5 C 1.1465(4) 0.6158(4) 0.4497(4) 0.0445(9) Uani 1 d . . . C6 C 0.6594(3) 0.6595(3) 0.4946(3) 0.0291(6) Uani 1 d . . . C7 C 0.5692(4) 0.8382(3) 0.6321(4) 0.0393(8) Uani 1 d . . . H1 H 1.102(5) 0.712(4) 0.270(5) 0.036(10) Uiso 1 d . . . H3A H 0.917(5) 0.596(4) 0.629(5) 0.036(10) Uiso 1 d . . . H3B H 0.852(5) 0.469(5) 0.619(5) 0.050(12) Uiso 1 d . . . H4A H 1.059(4) 0.425(4) 0.439(4) 0.029(9) Uiso 1 d . . . H4B H 1.125(6) 0.465(6) 0.575(6) 0.063(14) Uiso 1 d . . . H5A H 1.180(5) 0.690(4) 0.533(4) 0.038(10) Uiso 1 d . . . H5B H 1.233(5) 0.590(4) 0.401(4) 0.037(10) Uiso 1 d . . . H7A H 0.531(5) 0.884(5) 0.545(5) 0.041(10) Uiso 1 d . . . H7B H 0.482(5) 0.789(4) 0.667(4) 0.037(10) Uiso 1 d . . . H7C H 0.628(5) 0.898(4) 0.716(5) 0.044(11) Uiso 1 d . . . F11 F 0.2797(2) 0.66201(19) 0.82147(19) 0.0373(4) Uani 1 d . . . O11 O 0.2890(3) 0.7040(2) 1.1254(2) 0.0364(5) Uani 1 d . . . O12 O 0.1743(2) 0.4135(2) 1.0648(2) 0.0332(5) Uani 1 d . . . O13 O 0.0326(3) 0.5222(2) 0.8952(2) 0.0366(5) Uani 1 d . . . N11 N 0.5238(3) 0.6050(3) 1.0965(3) 0.0340(6) Uani 1 d . . . C11 C 0.3759(3) 0.6296(3) 1.0590(3) 0.0284(6) Uani 1 d . . . C12 C 0.3111(3) 0.5620(3) 0.9204(3) 0.0280(6) Uani 1 d . . . C13 C 0.4223(4) 0.4644(4) 0.8494(4) 0.0360(7) Uani 1 d . . . C14 C 0.5908(4) 0.5122(3) 0.8589(3) 0.0353(7) Uani 1 d . . . C15 C 0.6367(4) 0.5246(4) 1.0182(4) 0.0360(7) Uani 1 d . . . C16 C 0.1539(4) 0.4991(3) 0.9564(3) 0.0302(6) Uani 1 d . . . C17 C 0.0352(4) 0.3397(4) 1.1030(4) 0.0389(8) Uani 1 d . . . H11 H 0.562(5) 0.639(5) 1.183(5) 0.044(11) Uiso 1 d . . . H13A H 0.424(4) 0.391(4) 0.906(4) 0.029(9) Uiso 1 d . . . H13B H 0.391(5) 0.445(5) 0.742(5) 0.048(11) Uiso 1 d . . . H14A H 0.667(5) 0.452(5) 0.816(5) 0.052(12) Uiso 1 d . . . H14B H 0.607(4) 0.608(3) 0.818(4) 0.022(7) Uiso 1 d . . . H15A H 0.727(5) 0.567(4) 1.039(4) 0.040(10) Uiso 1 d . . . H15B H 0.634(4) 0.446(4) 1.062(4) 0.025(8) Uiso 1 d . . . H17A H -0.054(6) 0.392(6) 1.141(6) 0.062(14) Uiso 1 d . . . H17B H 0.080(6) 0.274(6) 1.157(6) 0.060(13) Uiso 1 d . . . H17C H 0.001(6) 0.287(5) 1.026(6) 0.053(13) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0353(10) 0.0330(10) 0.0403(9) -0.0085(8) 0.0042(7) -0.0048(7) O1 0.0373(12) 0.0391(13) 0.0366(11) 0.0058(10) -0.0053(9) 0.0002(10) O2 0.0259(10) 0.0286(11) 0.0382(11) -0.0036(9) 0.0031(8) 0.0010(8) O3 0.0279(13) 0.0601(17) 0.0667(17) -0.0280(14) -0.0017(10) 0.0025(11) N1 0.0299(14) 0.0441(16) 0.0345(13) 0.0032(12) 0.0043(11) -0.0034(11) C1 0.0294(15) 0.0269(14) 0.0272(13) -0.0034(12) -0.0001(10) 0.0020(11) C2 0.0287(15) 0.0298(15) 0.0311(15) -0.0022(12) -0.0003(11) 0.0014(12) C3 0.0395(18) 0.0349(18) 0.0325(16) 0.0007(14) 0.0013(13) 0.0095(13) C4 0.0382(18) 0.0440(19) 0.0340(16) 0.0017(16) -0.0027(13) 0.0140(15) C5 0.0248(16) 0.063(2) 0.0454(18) -0.0004(18) -0.0069(13) 0.0013(15) C6 0.0240(14) 0.0297(14) 0.0335(14) 0.0023(12) 0.0012(10) -0.0036(11) C7 0.0353(17) 0.0341(17) 0.049(2) -0.0039(16) 0.0083(14) 0.0051(13) F11 0.0375(10) 0.0415(10) 0.0329(9) 0.0084(8) -0.0010(7) -0.0028(8) O11 0.0341(11) 0.0373(12) 0.0377(11) -0.0051(9) 0.0040(9) 0.0003(9) O12 0.0299(11) 0.0362(12) 0.0337(11) 0.0068(9) -0.0019(8) -0.0033(9) O13 0.0281(12) 0.0449(13) 0.0368(11) 0.0035(10) -0.0023(9) 0.0001(9) N11 0.0308(14) 0.0377(15) 0.0334(14) -0.0044(11) -0.0032(10) 0.0029(11) C11 0.0288(14) 0.0273(14) 0.0291(14) 0.0017(11) 0.0039(11) -0.0033(11) C12 0.0253(15) 0.0301(15) 0.0288(14) 0.0034(11) 0.0006(10) 0.0008(11) C13 0.0344(17) 0.0416(18) 0.0322(15) -0.0051(14) 0.0013(11) 0.0015(13) C14 0.0309(17) 0.0386(17) 0.0366(16) 0.0022(14) 0.0067(12) 0.0036(13) C15 0.0289(17) 0.0374(19) 0.0418(18) 0.0014(15) -0.0011(12) 0.0039(13) C16 0.0319(15) 0.0289(15) 0.0299(14) -0.0008(12) -0.0004(11) -0.0014(11) C17 0.0379(19) 0.0370(18) 0.0418(19) 0.0073(15) -0.0002(14) -0.0090(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.404(4) . ? O1 C1 1.226(4) . ? O2 C6 1.333(4) . ? O2 C7 1.465(4) . ? O3 C6 1.193(4) . ? N1 C1 1.333(4) . ? N1 C5 1.469(5) . ? N1 H1 0.86(5) . ? C1 C2 1.541(4) . ? C2 C3 1.514(4) . ? C2 C6 1.535(4) . ? C3 C4 1.503(5) . ? C3 H3A 0.83(5) . ? C3 H3B 0.95(5) . ? C4 C5 1.513(6) . ? C4 H4A 1.02(4) . ? C4 H4B 0.82(6) . ? C5 H5A 1.12(4) . ? C5 H5B 0.91(4) . ? C7 H7A 0.98(4) . ? C7 H7B 0.96(4) . ? C7 H7C 1.11(4) . ? F11 C12 1.396(3) . ? O11 C11 1.229(4) . ? O12 C16 1.337(4) . ? O12 C17 1.454(4) . ? O13 C16 1.196(4) . ? N11 C11 1.328(4) . ? N11 C15 1.461(4) . ? N11 H11 0.93(5) . ? C11 C12 1.546(4) . ? C12 C13 1.529(4) . ? C12 C16 1.526(4) . ? C13 C14 1.521(5) . ? C13 H13A 0.91(4) . ? C13 H13B 1.03(5) . ? C14 C15 1.511(5) . ? C14 H14A 0.98(5) . ? C14 H14B 1.06(4) . ? C15 H15A 0.91(5) . ? C15 H15B 0.91(4) . ? C17 H17A 1.00(5) . ? C17 H17B 0.92(6) . ? C17 H17C 0.94(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C7 115.0(2) . . ? C1 N1 C5 126.2(3) . . ? C1 N1 H1 122(3) . . ? C5 N1 H1 112(3) . . ? O1 C1 N1 124.3(3) . . ? O1 C1 C2 118.6(3) . . ? N1 C1 C2 117.1(3) . . ? F1 C2 C1 104.1(2) . . ? F1 C2 C3 108.4(3) . . ? F1 C2 C6 106.0(2) . . ? C3 C2 C1 116.2(3) . . ? C3 C2 C6 113.8(2) . . ? C6 C2 C1 107.4(2) . . ? C2 C3 H3A 107(3) . . ? C2 C3 H3B 109(3) . . ? C4 C3 C2 110.1(3) . . ? C4 C3 H3A 109(3) . . ? C4 C3 H3B 115(3) . . ? H3A C3 H3B 106(4) . . ? C3 C4 C5 109.2(3) . . ? C3 C4 H4A 111(2) . . ? C3 C4 H4B 115(4) . . ? C5 C4 H4A 111(2) . . ? C5 C4 H4B 109(4) . . ? H4A C4 H4B 101(4) . . ? N1 C5 C4 110.8(3) . . ? N1 C5 H5A 109(2) . . ? N1 C5 H5B 105(3) . . ? C4 C5 H5A 114(2) . . ? C4 C5 H5B 109(3) . . ? H5A C5 H5B 109(3) . . ? O2 C6 C2 109.9(2) . . ? O3 C6 O2 125.4(3) . . ? O3 C6 C2 124.6(3) . . ? O2 C7 H7A 107(3) . . ? O2 C7 H7B 112(3) . . ? O2 C7 H7C 101(2) . . ? H7A C7 H7B 106(3) . . ? H7A C7 H7C 117(3) . . ? H7B C7 H7C 114(3) . . ? C16 O12 C17 114.9(2) . . ? C11 N11 C15 127.4(3) . . ? C11 N11 H11 119(3) . . ? C15 N11 H11 114(3) . . ? O11 C11 N11 124.4(3) . . ? O11 C11 C12 118.2(3) . . ? N11 C11 C12 117.4(3) . . ? F11 C12 C11 105.3(2) . . ? F11 C12 C13 109.1(2) . . ? F11 C12 C16 106.7(2) . . ? C13 C12 C11 115.2(2) . . ? C16 C12 C11 108.9(2) . . ? C16 C12 C13 111.1(3) . . ? C12 C13 H13A 108(2) . . ? C12 C13 H13B 112(3) . . ? C14 C13 C12 110.5(3) . . ? C14 C13 H13A 103(2) . . ? C14 C13 H13B 111(3) . . ? H13A C13 H13B 112(3) . . ? C13 C14 H14A 113(3) . . ? C13 C14 H14B 113.7(17) . . ? C15 C14 C13 108.7(3) . . ? C15 C14 H14A 106(3) . . ? C15 C14 H14B 103.1(18) . . ? H14A C14 H14B 111(3) . . ? N11 C15 C14 110.7(3) . . ? N11 C15 H15A 101(3) . . ? N11 C15 H15B 106(2) . . ? C14 C15 H15A 117(3) . . ? C14 C15 H15B 110(2) . . ? H15A C15 H15B 111(4) . . ? O12 C16 C12 109.2(2) . . ? O13 C16 O12 125.9(3) . . ? O13 C16 C12 124.9(3) . . ? O12 C17 H17A 115(3) . . ? O12 C17 H17B 100(3) . . ? O12 C17 H17C 112(3) . . ? H17A C17 H17B 122(4) . . ? H17A C17 H17C 110(4) . . ? H17B C17 H17C 96(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O11 0.86(5) 2.08(4) 2.857(4) 150(4) 1_654 N11 H11 O1 0.93(5) 2.37(4) 3.051(3) 130(3) 1_556 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C2 C3 C4 76.8(3) . . . . ? F1 C2 C6 O2 174.0(2) . . . . ? F1 C2 C6 O3 -7.5(4) . . . . ? O1 C1 C2 F1 69.8(3) . . . . ? O1 C1 C2 C3 -171.0(3) . . . . ? O1 C1 C2 C6 -42.3(3) . . . . ? N1 C1 C2 F1 -107.3(3) . . . . ? N1 C1 C2 C3 11.9(4) . . . . ? N1 C1 C2 C6 140.6(3) . . . . ? C1 N1 C5 C4 27.5(5) . . . . ? C1 C2 C3 C4 -39.9(4) . . . . ? C1 C2 C6 O2 -75.3(3) . . . . ? C1 C2 C6 O3 103.3(4) . . . . ? C2 C3 C4 C5 61.3(4) . . . . ? C3 C2 C6 O2 54.9(3) . . . . ? C3 C2 C6 O3 -126.6(4) . . . . ? C3 C4 C5 N1 -54.4(4) . . . . ? C5 N1 C1 O1 177.4(3) . . . . ? C5 N1 C1 C2 -5.7(5) . . . . ? C6 C2 C3 C4 -165.5(3) . . . . ? C7 O2 C6 O3 -3.2(5) . . . . ? C7 O2 C6 C2 175.4(2) . . . . ? F11 C12 C13 C14 80.9(3) . . . . ? F11 C12 C16 O12 -172.2(2) . . . . ? F11 C12 C16 O13 8.8(4) . . . . ? O11 C11 C12 F11 63.5(3) . . . . ? O11 C11 C12 C13 -176.2(3) . . . . ? O11 C11 C12 C16 -50.7(4) . . . . ? N11 C11 C12 F11 -115.2(3) . . . . ? N11 C11 C12 C13 5.1(4) . . . . ? N11 C11 C12 C16 130.6(3) . . . . ? C11 N11 C15 C14 22.3(5) . . . . ? C11 C12 C13 C14 -37.3(4) . . . . ? C11 C12 C16 O12 -58.9(3) . . . . ? C11 C12 C16 O13 122.0(3) . . . . ? C12 C13 C14 C15 61.8(4) . . . . ? C13 C12 C16 O12 69.0(3) . . . . ? C13 C12 C16 O13 -110.1(4) . . . . ? C13 C14 C15 N11 -53.6(4) . . . . ? C15 N11 C11 O11 -175.8(3) . . . . ? C15 N11 C11 C12 2.8(5) . . . . ? C16 C12 C13 C14 -161.7(3) . . . . ? C17 O12 C16 O13 3.2(5) . . . . ? C17 O12 C16 C12 -175.8(3) . . . . ? _iucr_refinement_instructions_details ; TITL 14srv257 in P21 #4 REM reset to P21 #4 CELL 1.54178 8.5224 10.305 9.1442 90 90.3404 90 ZERR 4 0.0004 0.0005 0.0004 0 0.0011 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H F N O UNIT 28 40 4 4 12 EQIV $1 1+X,+Y,-1+Z EQIV $2 +X,+Y,1+Z L.S. 9 PLAN 5 TEMP -153.15 HTAB N1 O11_$1 HTAB N11 O1_$2 BOND $h CONF fmap 2 53 acta OMIT -2 145 OMIT 2 0 9 OMIT 1 0 1 OMIT 0 2 9 OMIT 2 3 9 WGHT 0.1 0.5 FVAR 0.38693 REM REM REM F1 3 0.75331 0.48062 0.36230 11.00000 0.03532 0.03303 0.04028 = -0.00847 0.00420 -0.00485 O1 5 0.81082 0.72976 0.23958 11.00000 0.03730 0.03909 0.03655 = 0.00581 -0.00526 0.00017 O2 5 0.69916 0.75516 0.58583 11.00000 0.02595 0.02860 0.03824 = -0.00364 0.00308 0.00104 O3 5 0.52916 0.63509 0.45480 11.00000 0.02792 0.06012 0.06666 = -0.02801 -0.00173 0.00253 N1 4 1.04671 0.67724 0.33792 11.00000 0.02990 0.04413 0.03447 = 0.00317 0.00428 -0.00342 C1 1 0.89047 0.67344 0.33192 11.00000 0.02941 0.02694 0.02725 = -0.00340 -0.00008 0.00198 C2 1 0.80691 0.58688 0.44466 11.00000 0.02869 0.02982 0.03106 = -0.00224 -0.00027 0.00138 C3 1 0.90740 0.53632 0.56934 11.00000 0.03950 0.03488 0.03250 = 0.00070 0.00125 0.00947 C4 1 1.06641 0.49795 0.51375 11.00000 0.03821 0.04401 0.03403 = 0.00166 -0.00273 0.01403 C5 1 1.14650 0.61581 0.44968 11.00000 0.02478 0.06330 0.04545 = -0.00044 -0.00691 0.00128 C6 1 0.65938 0.65954 0.49463 11.00000 0.02403 0.02974 0.03352 = 0.00233 0.00119 -0.00365 C7 1 0.56917 0.83824 0.63209 11.00000 0.03527 0.03405 0.04855 = -0.00391 0.00829 0.00512 H1 2 1.10179 0.71243 0.26997 11.00000 0.03598 H3a 2 0.91723 0.59641 0.62930 11.00000 0.03641 H3b 2 0.85209 0.46909 0.61893 11.00000 0.05003 H4a 2 1.05865 0.42453 0.43872 11.00000 0.02887 H4b 2 1.12505 0.46481 0.57528 11.00000 0.06294 H5a 2 1.18006 0.69004 0.53304 11.00000 0.03772 H5b 2 1.23336 0.59025 0.40058 11.00000 0.03699 H7a 2 0.53057 0.88371 0.54476 11.00000 0.04055 H7b 2 0.48197 0.78888 0.66711 11.00000 0.03686 H7c 2 0.62802 0.89823 0.71646 11.00000 0.04414 F11 3 0.27969 0.66201 0.82147 11.00000 0.03754 0.04151 0.03290 = 0.00844 -0.00101 -0.00280 O11 5 0.28904 0.70404 1.12544 11.00000 0.03413 0.03731 0.03774 = -0.00515 0.00402 0.00030 O12 5 0.17430 0.41350 1.06477 11.00000 0.02990 0.03616 0.03366 = 0.00680 -0.00187 -0.00330 O13 5 0.03261 0.52221 0.89522 11.00000 0.02810 0.04491 0.03676 = 0.00355 -0.00226 0.00007 N11 4 0.52375 0.60498 1.09655 11.00000 0.03077 0.03767 0.03339 = -0.00438 -0.00316 0.00288 C11 1 0.37594 0.62960 1.05898 11.00000 0.02879 0.02730 0.02911 = 0.00167 0.00388 -0.00327 C12 1 0.31112 0.56198 0.92037 11.00000 0.02527 0.03007 0.02878 = 0.00339 0.00057 0.00077 C13 1 0.42230 0.46437 0.84944 11.00000 0.03438 0.04158 0.03217 = -0.00507 0.00129 0.00151 C14 1 0.59084 0.51224 0.85893 11.00000 0.03087 0.03863 0.03661 = 0.00222 0.00668 0.00362 C15 1 0.63666 0.52458 1.01821 11.00000 0.02890 0.03741 0.04180 = 0.00143 -0.00111 0.00387 C16 1 0.15391 0.49909 0.95638 11.00000 0.03191 0.02891 0.02985 = -0.00083 -0.00038 -0.00139 C17 1 0.03515 0.33965 1.10303 11.00000 0.03789 0.03700 0.04180 = 0.00727 -0.00018 -0.00901 H11 2 0.56242 0.63943 1.18334 11.00000 0.04408 H13a 2 0.42425 0.39146 0.90602 11.00000 0.02924 H13b 2 0.39140 0.44476 0.74233 11.00000 0.04822 H14a 2 0.66664 0.45151 0.81573 11.00000 0.05244 H14b 2 0.60653 0.60752 0.81844 11.00000 0.02163 H15a 2 0.72722 0.56680 1.03941 11.00000 0.04025 H15b 2 0.63419 0.44590 1.06248 11.00000 0.02455 H17a 2 -0.05407 0.39239 1.14136 11.00000 0.06207 H17b 2 0.08033 0.27428 1.15700 11.00000 0.05966 H17c 2 0.00050 0.28659 1.02560 11.00000 0.05256 HKLF 4 END ; ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_2c_14srv258 _database_code_depnum_ccdc_archive 'CCDC 1401918' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2014-11-24 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949) ; _chemical_name_common ? _chemical_name_systematic ; (R)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate ; _chemical_formula_moiety 'C7 H10 F N O3' _chemical_formula_sum 'C7 H10 F N O3' _chemical_formula_weight 175.16 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 8.5211(3) _cell_length_b 10.3039(3) _cell_length_c 9.1547(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.3650(8) _cell_angle_gamma 90.00 _cell_volume 803.77(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7543 _cell_measurement_temperature 120.0(2) _cell_measurement_theta_max 74.36 _cell_measurement_theta_min 4.29 _exptl_absorpt_coefficient_mu 1.104 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8531 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1118 before and 0.0883 after correction. The Ratio of minimum to maximum transmission is 0.8531. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_unetI/netI 0.0613 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6957 _diffrn_reflns_theta_full 72.47 _diffrn_reflns_theta_max 72.47 _diffrn_reflns_theta_min 4.83 _diffrn_ambient_temperature 120.0 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device 'Bruker D8 Venture' _diffrn_measurement_device_type '3-circle diffractometer' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'ImuS microsource' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2893 _reflns_number_total 2916 _reflns_threshold_expression >2sigma(I) _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.328 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.067 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(16) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 2916 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0513 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1451 _refine_ls_wR_factor_ref 0.1455 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.74634(17) 0.54728(15) 0.13756(16) 0.0368(4) Uani 1 d . . . O1 O 0.6903(2) 0.29830(19) 0.2600(2) 0.0373(4) Uani 1 d . . . O2 O 0.80105(19) 0.27347(17) -0.08541(19) 0.0311(4) Uani 1 d . . . O3 O 0.9704(2) 0.3938(3) 0.0451(3) 0.0528(6) Uani 1 d . . . N1 N 0.4532(3) 0.3510(2) 0.1621(2) 0.0358(5) Uani 1 d . . . C1 C 0.6094(3) 0.3546(2) 0.1680(2) 0.0286(5) Uani 1 d . . . C2 C 0.6929(3) 0.4414(2) 0.0549(3) 0.0290(5) Uani 1 d . . . C3 C 0.5934(3) 0.4920(3) -0.0694(3) 0.0346(6) Uani 1 d . . . C4 C 0.4317(3) 0.5305(3) -0.0134(3) 0.0379(6) Uani 1 d . . . C5 C 0.3524(3) 0.4125(3) 0.0507(3) 0.0440(7) Uani 1 d . . . C6 C 0.8403(3) 0.3682(2) 0.0053(3) 0.0299(5) Uani 1 d . . . C7 C 0.9305(3) 0.1902(3) -0.1316(3) 0.0396(6) Uani 1 d . . . H1 H 0.411(4) 0.319(4) 0.234(4) 0.036(8) Uiso 1 d . . . H3A H 0.582(5) 0.432(4) -0.137(4) 0.052(10) Uiso 1 d . . . H3B H 0.650(5) 0.563(4) -0.117(4) 0.051(10) Uiso 1 d . . . H4A H 0.444(4) 0.599(3) 0.055(4) 0.031(7) Uiso 1 d . . . H4B H 0.371(3) 0.560(3) -0.097(3) 0.019(6) Uiso 1 d . . . H5A H 0.263(4) 0.444(4) 0.098(4) 0.038(8) Uiso 1 d . . . H5B H 0.321(4) 0.344(4) -0.037(4) 0.046(9) Uiso 1 d . . . H7A H 0.874(4) 0.137(3) -0.217(4) 0.035(8) Uiso 1 d . . . H7B H 0.961(5) 0.139(5) -0.055(5) 0.056(11) Uiso 1 d . . . H7C H 1.001(5) 0.244(4) -0.177(4) 0.047(9) Uiso 1 d . . . F11 F 0.21984(18) 0.36622(16) 0.67839(16) 0.0375(4) Uani 1 d . . . O11 O 0.2110(2) 0.32427(19) 0.3745(2) 0.0360(4) Uani 1 d . . . O12 O 0.3261(2) 0.61490(19) 0.43529(19) 0.0342(4) Uani 1 d . . . O13 O 0.4675(2) 0.50597(19) 0.6046(2) 0.0355(4) Uani 1 d . . . N11 N -0.0241(2) 0.4225(2) 0.4037(2) 0.0338(5) Uani 1 d . . . C11 C 0.1242(3) 0.3988(2) 0.4416(3) 0.0298(5) Uani 1 d . . . C12 C 0.1891(3) 0.4664(2) 0.5796(3) 0.0289(5) Uani 1 d . . . C13 C 0.0769(3) 0.5633(3) 0.6508(3) 0.0354(5) Uani 1 d . . . C14 C -0.0918(3) 0.5154(3) 0.6408(3) 0.0354(5) Uani 1 d . . . C15 C -0.1381(3) 0.5033(3) 0.4817(3) 0.0361(6) Uani 1 d . . . C16 C 0.3466(3) 0.5293(2) 0.5431(2) 0.0297(5) Uani 1 d . . . C17 C 0.4646(3) 0.6888(3) 0.3979(3) 0.0391(6) Uani 1 d . . . H11 H -0.057(4) 0.396(4) 0.329(4) 0.045(9) Uiso 1 d . . . H13A H 0.095(4) 0.647(4) 0.600(4) 0.036(8) Uiso 1 d . . . H13B H 0.104(5) 0.584(4) 0.749(5) 0.057(11) Uiso 1 d . . . H14A H -0.170(4) 0.576(4) 0.692(4) 0.040(8) Uiso 1 d . . . H14B H -0.101(4) 0.433(4) 0.687(4) 0.038(8) Uiso 1 d . . . H15A H -0.141(3) 0.591(3) 0.438(3) 0.019(6) Uiso 1 d . . . H15B H -0.231(4) 0.461(4) 0.473(4) 0.037(8) Uiso 1 d . . . H17A H 0.422(4) 0.742(5) 0.328(4) 0.050(10) Uiso 1 d . . . H17B H 0.544(6) 0.625(6) 0.345(6) 0.083(15) Uiso 1 d . . . H17C H 0.502(4) 0.726(4) 0.472(4) 0.039(9) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0366(8) 0.0332(8) 0.0406(8) -0.0089(6) 0.0044(6) -0.0034(6) O1 0.0364(9) 0.0395(10) 0.0359(9) 0.0050(8) -0.0047(7) 0.0011(8) O2 0.0261(8) 0.0285(8) 0.0388(9) -0.0028(7) 0.0027(6) 0.0022(7) O3 0.0252(9) 0.0621(14) 0.0711(15) -0.0277(12) -0.0060(8) 0.0026(9) N1 0.0280(10) 0.0436(12) 0.0358(11) 0.0039(10) 0.0019(8) -0.0002(9) C1 0.0293(11) 0.0297(11) 0.0269(10) -0.0024(9) -0.0018(8) 0.0014(9) C2 0.0267(11) 0.0295(11) 0.0308(11) -0.0014(9) -0.0001(8) 0.0012(10) C3 0.0338(13) 0.0390(14) 0.0308(12) 0.0008(11) 0.0014(10) 0.0104(10) C4 0.0347(13) 0.0437(14) 0.0352(12) 0.0006(12) -0.0027(10) 0.0125(11) C5 0.0224(11) 0.0600(19) 0.0495(15) 0.0010(14) -0.0063(10) 0.0030(12) C6 0.0216(10) 0.0325(11) 0.0356(11) 0.0019(10) 0.0010(8) -0.0004(9) C7 0.0346(13) 0.0344(13) 0.0499(15) -0.0038(13) 0.0077(11) 0.0074(11) F11 0.0376(7) 0.0408(8) 0.0342(7) 0.0103(6) -0.0012(6) -0.0015(6) O11 0.0339(9) 0.0364(9) 0.0379(9) -0.0046(7) 0.0045(7) 0.0015(7) O12 0.0317(9) 0.0370(9) 0.0339(9) 0.0067(7) -0.0033(7) -0.0045(7) O13 0.0292(9) 0.0400(10) 0.0374(9) 0.0042(8) -0.0028(7) -0.0013(7) N11 0.0304(10) 0.0371(12) 0.0338(11) -0.0030(9) -0.0052(8) 0.0009(9) C11 0.0300(11) 0.0279(11) 0.0315(11) 0.0016(9) 0.0018(9) -0.0039(9) C12 0.0285(12) 0.0295(12) 0.0286(11) 0.0026(9) -0.0023(8) 0.0005(9) C13 0.0319(12) 0.0406(14) 0.0338(12) -0.0069(11) 0.0017(9) -0.0010(10) C14 0.0307(12) 0.0391(14) 0.0365(12) 0.0032(11) 0.0041(9) 0.0038(10) C15 0.0295(12) 0.0396(14) 0.0393(13) 0.0003(11) -0.0030(9) 0.0030(11) C16 0.0310(11) 0.0294(11) 0.0287(10) -0.0024(9) -0.0026(8) -0.0013(9) C17 0.0398(14) 0.0385(14) 0.0391(14) 0.0063(12) -0.0015(11) -0.0119(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.402(3) . ? O1 C1 1.230(3) . ? O2 C6 1.323(3) . ? O2 C7 1.462(3) . ? O3 C6 1.195(3) . ? N1 C1 1.332(3) . ? N1 C5 1.472(4) . ? N1 H1 0.82(4) . ? C1 C2 1.545(3) . ? C2 C3 1.507(3) . ? C2 C6 1.536(3) . ? C3 C4 1.525(4) . ? C3 H3A 0.88(4) . ? C3 H3B 0.98(4) . ? C4 C5 1.512(4) . ? C4 H4A 0.95(4) . ? C4 H4B 0.97(3) . ? C5 H5A 0.94(4) . ? C5 H5B 1.10(4) . ? C7 H7A 1.07(3) . ? C7 H7B 0.91(4) . ? C7 H7C 0.91(4) . ? F11 C12 1.396(3) . ? O11 C11 1.234(3) . ? O12 C16 1.334(3) . ? O12 C17 1.447(3) . ? O13 C16 1.195(3) . ? N11 C11 1.331(3) . ? N11 C15 1.468(3) . ? N11 H11 0.79(4) . ? C11 C12 1.542(3) . ? C12 C13 1.530(3) . ? C12 C16 1.529(3) . ? C13 C14 1.522(4) . ? C13 H13A 0.99(4) . ? C13 H13B 0.95(4) . ? C14 C15 1.512(4) . ? C14 H14A 1.03(4) . ? C14 H14B 0.95(4) . ? C15 H15A 0.99(3) . ? C15 H15B 0.91(4) . ? C17 H17A 0.92(4) . ? C17 H17B 1.06(6) . ? C17 H17C 0.84(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C7 115.23(19) . . ? C1 N1 C5 126.5(2) . . ? C1 N1 H1 115(2) . . ? C5 N1 H1 118(2) . . ? O1 C1 N1 124.8(2) . . ? O1 C1 C2 118.3(2) . . ? N1 C1 C2 116.9(2) . . ? F1 C2 C1 103.74(18) . . ? F1 C2 C3 108.5(2) . . ? F1 C2 C6 106.14(18) . . ? C3 C2 C1 116.5(2) . . ? C3 C2 C6 113.84(19) . . ? C6 C2 C1 107.14(19) . . ? C2 C3 C4 109.9(2) . . ? C2 C3 H3A 110(3) . . ? C2 C3 H3B 109(2) . . ? C4 C3 H3A 109(3) . . ? C4 C3 H3B 114(2) . . ? H3A C3 H3B 105(3) . . ? C3 C4 H4A 108.7(19) . . ? C3 C4 H4B 106.9(16) . . ? C5 C4 C3 109.2(2) . . ? C5 C4 H4A 113(2) . . ? C5 C4 H4B 108.7(17) . . ? H4A C4 H4B 110(3) . . ? N1 C5 C4 110.7(2) . . ? N1 C5 H5A 108(2) . . ? N1 C5 H5B 112(2) . . ? C4 C5 H5A 105(2) . . ? C4 C5 H5B 110(2) . . ? H5A C5 H5B 111(3) . . ? O2 C6 C2 110.10(19) . . ? O3 C6 O2 125.8(2) . . ? O3 C6 C2 124.1(2) . . ? O2 C7 H7A 100.1(18) . . ? O2 C7 H7B 109(3) . . ? O2 C7 H7C 106(3) . . ? H7A C7 H7B 113(3) . . ? H7A C7 H7C 106(3) . . ? H7B C7 H7C 121(3) . . ? C16 O12 C17 114.81(19) . . ? C11 N11 C15 127.4(2) . . ? C11 N11 H11 120(3) . . ? C15 N11 H11 113(3) . . ? O11 C11 N11 123.7(2) . . ? O11 C11 C12 118.5(2) . . ? N11 C11 C12 117.8(2) . . ? F11 C12 C11 105.15(19) . . ? F11 C12 C13 108.76(19) . . ? F11 C12 C16 107.08(18) . . ? C13 C12 C11 114.9(2) . . ? C16 C12 C11 108.84(19) . . ? C16 C12 C13 111.6(2) . . ? C12 C13 H13A 106(2) . . ? C12 C13 H13B 113(3) . . ? C14 C13 C12 110.8(2) . . ? C14 C13 H13A 113.6(19) . . ? C14 C13 H13B 111(3) . . ? H13A C13 H13B 102(3) . . ? C13 C14 H14A 113(2) . . ? C13 C14 H14B 110(2) . . ? C15 C14 C13 109.0(2) . . ? C15 C14 H14A 108.7(19) . . ? C15 C14 H14B 110(2) . . ? H14A C14 H14B 107(3) . . ? N11 C15 C14 110.3(2) . . ? N11 C15 H15A 109.5(17) . . ? N11 C15 H15B 106(2) . . ? C14 C15 H15A 108.7(16) . . ? C14 C15 H15B 110(2) . . ? H15A C15 H15B 112(3) . . ? O12 C16 C12 109.32(19) . . ? O13 C16 O12 126.1(2) . . ? O13 C16 C12 124.5(2) . . ? O12 C17 H17A 99(2) . . ? O12 C17 H17B 108(3) . . ? O12 C17 H17C 110(3) . . ? H17A C17 H17B 108(4) . . ? H17A C17 H17C 116(4) . . ? H17B C17 H17C 115(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O11 0.82(4) 2.14(4) 2.858(3) 145(3) . N11 H11 O1 0.79(4) 2.46(4) 3.042(3) 132(3) 1_455 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C2 C3 C4 -77.0(3) . . . . ? F1 C2 C6 O2 -174.02(19) . . . . ? F1 C2 C6 O3 6.6(3) . . . . ? O1 C1 C2 F1 -69.9(3) . . . . ? O1 C1 C2 C3 170.9(2) . . . . ? O1 C1 C2 C6 42.1(3) . . . . ? N1 C1 C2 F1 107.3(2) . . . . ? N1 C1 C2 C3 -11.9(3) . . . . ? N1 C1 C2 C6 -140.7(2) . . . . ? C1 N1 C5 C4 -27.6(4) . . . . ? C1 C2 C3 C4 39.6(3) . . . . ? C1 C2 C6 O2 75.6(2) . . . . ? C1 C2 C6 O3 -103.8(3) . . . . ? C2 C3 C4 C5 -60.9(3) . . . . ? C3 C2 C6 O2 -54.7(3) . . . . ? C3 C2 C6 O3 125.9(3) . . . . ? C3 C4 C5 N1 54.0(3) . . . . ? C5 N1 C1 O1 -177.3(3) . . . . ? C5 N1 C1 C2 5.7(4) . . . . ? C6 C2 C3 C4 165.1(2) . . . . ? C7 O2 C6 O3 3.9(4) . . . . ? C7 O2 C6 C2 -175.51(19) . . . . ? F11 C12 C13 C14 -80.8(2) . . . . ? F11 C12 C16 O12 172.25(19) . . . . ? F11 C12 C16 O13 -9.0(3) . . . . ? O11 C11 C12 F11 -63.9(3) . . . . ? O11 C11 C12 C13 176.5(2) . . . . ? O11 C11 C12 C16 50.5(3) . . . . ? N11 C11 C12 F11 114.7(2) . . . . ? N11 C11 C12 C13 -4.9(3) . . . . ? N11 C11 C12 C16 -130.9(2) . . . . ? C11 N11 C15 C14 -22.7(4) . . . . ? C11 C12 C13 C14 36.7(3) . . . . ? C11 C12 C16 O12 59.1(3) . . . . ? C11 C12 C16 O13 -122.2(3) . . . . ? C12 C13 C14 C15 -61.7(3) . . . . ? C13 C12 C16 O12 -68.8(2) . . . . ? C13 C12 C16 O13 109.9(3) . . . . ? C13 C14 C15 N11 53.6(3) . . . . ? C15 N11 C11 O11 176.1(2) . . . . ? C15 N11 C11 C12 -2.4(4) . . . . ? C16 C12 C13 C14 161.3(2) . . . . ? C17 O12 C16 O13 -3.3(4) . . . . ? C17 O12 C16 C12 175.4(2) . . . . ? _iucr_refinement_instructions_details ; TITL 14srv258 in P21 #4 REM reset to P21 #4 CELL 1.54178 8.5211 10.3039 9.1547 90 90.365 90 ZERR 4 0.0003 0.0003 0.0003 0 0.0008 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H F N O UNIT 28 40 4 4 12 EQIV $1 -1+X,+Y,+Z L.S. 9 0 0 PLAN 5 TEMP -273.15 HTAB N1 O11 HTAB N11 O1_$1 CONF BOND $h fmap 2 53 acta OMIT -2 145 WGHT 0.1 0.12 FVAR 0.32691 REM REM REM F1 3 0.74634 0.54728 0.13756 11.00000 0.03657 0.03319 0.04063 = -0.00886 0.00444 -0.00345 O1 5 0.69026 0.29830 0.26000 11.00000 0.03638 0.03953 0.03590 = 0.00500 -0.00473 0.00110 O2 5 0.80105 0.27347 -0.08541 11.00000 0.02611 0.02855 0.03881 = -0.00280 0.00273 0.00224 O3 5 0.97044 0.39383 0.04513 11.00000 0.02519 0.06207 0.07111 = -0.02771 -0.00600 0.00258 N1 4 0.45321 0.35103 0.16206 11.00000 0.02801 0.04359 0.03576 = 0.00393 0.00189 -0.00022 C1 1 0.60936 0.35463 0.16801 11.00000 0.02928 0.02974 0.02689 = -0.00240 -0.00184 0.00140 C2 1 0.69287 0.44142 0.05486 11.00000 0.02674 0.02950 0.03079 = -0.00137 -0.00012 0.00115 C3 1 0.59337 0.49201 -0.06939 11.00000 0.03385 0.03905 0.03079 = 0.00082 0.00136 0.01040 C4 1 0.43174 0.53049 -0.01338 11.00000 0.03475 0.04373 0.03520 = 0.00062 -0.00275 0.01250 C5 1 0.35235 0.41247 0.05067 11.00000 0.02240 0.06002 0.04949 = 0.00097 -0.00631 0.00303 C6 1 0.84030 0.36820 0.00531 11.00000 0.02155 0.03252 0.03558 = 0.00189 0.00104 -0.00035 C7 1 0.93047 0.19021 -0.13157 11.00000 0.03465 0.03440 0.04991 = -0.00385 0.00774 0.00739 H1 2 0.41121 0.31873 0.23392 11.00000 0.03550 H3a 2 0.58228 0.43172 -0.13685 11.00000 0.05217 H3b 2 0.64987 0.56327 -0.11740 11.00000 0.05110 H4a 2 0.44389 0.59910 0.05549 11.00000 0.03099 H4b 2 0.37150 0.55964 -0.09690 11.00000 0.01904 H5a 2 0.26277 0.44405 0.09775 11.00000 0.03791 H5b 2 0.32084 0.34387 -0.03703 11.00000 0.04606 H7a 2 0.87360 0.13662 -0.21673 11.00000 0.03493 H7b 2 0.96120 0.13935 -0.05484 11.00000 0.05647 H7c 2 1.00056 0.24384 -0.17672 11.00000 0.04654 F11 3 0.21984 0.36622 0.67839 11.00000 0.03757 0.04085 0.03416 = 0.01025 -0.00123 -0.00153 O11 5 0.21100 0.32427 0.37446 11.00000 0.03385 0.03637 0.03791 = -0.00462 0.00451 0.00154 O12 5 0.32612 0.61490 0.43529 11.00000 0.03169 0.03701 0.03392 = 0.00672 -0.00333 -0.00450 O13 5 0.46753 0.50597 0.60458 11.00000 0.02916 0.03999 0.03741 = 0.00418 -0.00281 -0.00127 N11 4 -0.02409 0.42253 0.40367 11.00000 0.03042 0.03714 0.03376 = -0.00302 -0.00520 0.00094 C11 1 0.12419 0.39885 0.44162 11.00000 0.03003 0.02793 0.03146 = 0.00163 0.00181 -0.00388 C12 1 0.18912 0.46644 0.57964 11.00000 0.02852 0.02949 0.02857 = 0.00264 -0.00231 0.00053 C13 1 0.07692 0.56326 0.65082 11.00000 0.03185 0.04057 0.03381 = -0.00692 0.00168 -0.00104 C14 1 -0.09182 0.51538 0.64081 11.00000 0.03066 0.03905 0.03654 = 0.00322 0.00406 0.00381 C15 1 -0.13808 0.50331 0.48168 11.00000 0.02947 0.03956 0.03933 = 0.00032 -0.00298 0.00302 C16 1 0.34661 0.52931 0.54313 11.00000 0.03097 0.02943 0.02867 = -0.00237 -0.00258 -0.00130 C17 1 0.46460 0.68878 0.39790 11.00000 0.03977 0.03850 0.03908 = 0.00631 -0.00152 -0.01185 H11 2 -0.05711 0.39614 0.32857 11.00000 0.04483 H13a 2 0.09467 0.64659 0.60021 11.00000 0.03580 H13b 2 0.10450 0.58367 0.74876 11.00000 0.05659 H14a 2 -0.17022 0.57643 0.69180 11.00000 0.03951 H14b 2 -0.10053 0.43282 0.68723 11.00000 0.03847 H15a 2 -0.14052 0.59087 0.43794 11.00000 0.01891 H15b 2 -0.23148 0.46139 0.47291 11.00000 0.03685 H17a 2 0.42194 0.74213 0.32813 11.00000 0.04960 H17b 2 0.54419 0.62482 0.34490 11.00000 0.08319 H17c 2 0.50153 0.72614 0.47249 11.00000 0.03870 HKLF 4 END ; ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_4c_15srv065 _database_code_depnum_ccdc_archive 'CCDC 1401919' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2015-03-13 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _chemical_name_common ? _chemical_name_systematic ; dimethyl (2-aminopropyl)fluoromalonate hydrochloride ; _chemical_formula_moiety 'Cl, C8 H15 F N O4' _chemical_formula_sum 'C8 H15 Cl F N O4' _chemical_formula_weight 243.66 _chemical_melting_point ? _chemical_oxdiff_formula 'C8 H15 Cl1 F1 N1 O4' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 5.8210(4) _cell_length_b 6.4875(5) _cell_length_c 15.7485(12) _cell_angle_alpha 100.738(7) _cell_angle_beta 96.625(6) _cell_angle_gamma 94.612(6) _cell_volume 577.23(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3123 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.2490 _cell_measurement_theta_min 3.2000 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 256 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0444 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 8623 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.66 _diffrn_ambient_temperature 120.0 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -37.00 37.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -57.0000 120.0000 74 #__ type_ start__ end____ width___ exp.time_ 2 omega -1.00 75.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -112.0000 83.0000 76 #__ type_ start__ end____ width___ exp.time_ 3 omega -1.00 98.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 77.0000 -30.0000 99 #__ type_ start__ end____ width___ exp.time_ 4 omega -19.00 7.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 21.00 71.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -150.0000 50 #__ type_ start__ end____ width___ exp.time_ 6 omega -12.00 102.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 19.0000 -60.0000 114 #__ type_ start__ end____ width___ exp.time_ 7 omega -104.00 -35.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - -28.3337 -178.0000 -150.0000 69 #__ type_ start__ end____ width___ exp.time_ 8 omega -97.00 -7.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - -28.3337 -57.0000 30.0000 90 #__ type_ start__ end____ width___ exp.time_ 9 omega -1.00 38.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 77.0000 -150.0000 39 #__ type_ start__ end____ width___ exp.time_ 10 omega 3.00 101.00 1.0000 12.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 38.0000 150.0000 98 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 0.0842586000 _diffrn_orient_matrix_UB_12 0.0045224000 _diffrn_orient_matrix_UB_13 -0.0289226000 _diffrn_orient_matrix_UB_21 0.0897726000 _diffrn_orient_matrix_UB_22 0.0025254000 _diffrn_orient_matrix_UB_23 0.0348143000 _diffrn_orient_matrix_UB_31 -0.0074563000 _diffrn_orient_matrix_UB_32 -0.1117729000 _diffrn_orient_matrix_UB_33 -0.0095307000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2374 _reflns_number_total 2785 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.556 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.077 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2785 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0521 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1240 _refine_ls_wR_factor_ref 0.1289 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1D,H1E), C2(H2A,H2B), C3(H3A,H3B) 2.b Idealised Me refined as rotating group: N1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C) ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl1 Cl 0.75418(10) 1.29673(9) 0.51960(4) 0.02011(16) Uani 1 d . . . F1 F 0.6831(3) 0.9887(2) 0.17917(10) 0.0248(4) Uani 1 d . . . O1 O 0.5595(4) 0.7691(4) 0.01629(14) 0.0353(5) Uani 1 d . . . O2 O 0.1871(3) 0.7620(3) 0.04072(12) 0.0256(4) Uani 1 d . . . O3 O 0.3597(3) 0.5205(3) 0.19529(13) 0.0273(4) Uani 1 d . . . O4 O 0.7177(3) 0.6800(3) 0.24970(13) 0.0286(5) Uani 1 d . . . N1 N 0.2217(4) 1.1772(3) 0.44695(14) 0.0195(4) Uani 1 d . . . H1A H 0.2229 1.0478 0.4613 0.023 Uiso 1 calc . . GR H1B H 0.1086 1.2461 0.4719 0.023 Uiso 1 calc . . GR H1C H 0.3623 1.2530 0.4666 0.023 Uiso 1 calc . . GR C1 C 0.1745(5) 1.1523(4) 0.35047(17) 0.0227(5) Uani 1 d . . . H1D H 0.1831 1.2930 0.3345 0.027 Uiso 1 calc . . R H1E H 0.0157 1.0812 0.3295 0.027 Uiso 1 calc . . R C2 C 0.3501(4) 1.0233(4) 0.30724(17) 0.0203(5) Uani 1 d . . . H2A H 0.3518 0.8882 0.3278 0.024 Uiso 1 calc . . R H2B H 0.5072 1.1009 0.3242 0.024 Uiso 1 calc . . R C3 C 0.2916(5) 0.9785(4) 0.20797(17) 0.0206(5) Uani 1 d . . . H3A H 0.1380 0.8946 0.1910 0.025 Uiso 1 calc . . R H3B H 0.2815 1.1136 0.1878 0.025 Uiso 1 calc . . R C4 C 0.4737(4) 0.8589(4) 0.16362(17) 0.0188(5) Uani 1 d . . . C5 C 0.4151(5) 0.7910(4) 0.06354(17) 0.0215(5) Uani 1 d . . . C6 C 0.1074(6) 0.6948(5) -0.05202(18) 0.0320(7) Uani 1 d . . . H6A H 0.1722 0.7978 -0.0835 0.048 Uiso 1 calc . . GR H6B H -0.0628 0.6848 -0.0620 0.048 Uiso 1 calc . . GR H6C H 0.1590 0.5566 -0.0731 0.048 Uiso 1 calc . . GR C7 C 0.5104(4) 0.6631(4) 0.20300(16) 0.0196(5) Uani 1 d . . . C8 C 0.7546(7) 0.5106(5) 0.2970(2) 0.0450(9) Uani 1 d . . . H8A H 0.7465 0.3767 0.2554 0.068 Uiso 1 calc . . GR H8B H 0.6342 0.5019 0.3352 0.068 Uiso 1 calc . . GR H8C H 0.9080 0.5391 0.3322 0.068 Uiso 1 calc . . GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0160(3) 0.0143(3) 0.0302(3) 0.0050(2) 0.0028(2) 0.0012(2) F1 0.0211(8) 0.0210(8) 0.0318(9) 0.0086(6) 0.0015(6) -0.0064(6) O1 0.0295(11) 0.0484(13) 0.0288(11) 0.0056(10) 0.0077(9) 0.0071(10) O2 0.0227(10) 0.0319(10) 0.0215(10) 0.0081(8) 0.0000(7) -0.0038(8) O3 0.0314(11) 0.0161(9) 0.0331(11) 0.0079(8) -0.0020(8) -0.0038(8) O4 0.0290(11) 0.0172(9) 0.0372(11) 0.0071(8) -0.0089(9) 0.0037(8) N1 0.0172(10) 0.0139(9) 0.0272(11) 0.0020(8) 0.0043(8) 0.0029(8) C1 0.0219(13) 0.0192(12) 0.0263(13) 0.0025(10) 0.0004(10) 0.0060(10) C2 0.0214(13) 0.0167(11) 0.0229(13) 0.0038(10) 0.0017(10) 0.0053(10) C3 0.0229(13) 0.0159(11) 0.0232(13) 0.0048(10) 0.0007(10) 0.0047(10) C4 0.0165(12) 0.0139(11) 0.0255(13) 0.0064(10) 0.0005(10) -0.0027(9) C5 0.0259(14) 0.0159(11) 0.0235(13) 0.0066(10) 0.0022(10) 0.0016(10) C6 0.0348(16) 0.0369(16) 0.0216(14) 0.0082(12) -0.0037(12) -0.0075(13) C7 0.0221(13) 0.0162(11) 0.0203(12) 0.0026(9) 0.0023(10) 0.0035(10) C8 0.055(2) 0.0215(14) 0.053(2) 0.0121(14) -0.0272(17) 0.0069(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C4 1.394(3) . ? O1 C5 1.185(3) . ? O2 C5 1.323(3) . ? O2 C6 1.453(3) . ? O3 C7 1.202(3) . ? O4 C7 1.324(3) . ? O4 C8 1.454(3) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N1 C1 1.488(3) . ? C1 H1D 0.9900 . ? C1 H1E 0.9900 . ? C1 C2 1.515(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.528(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.521(4) . ? C4 C5 1.545(4) . ? C4 C7 1.533(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 C6 116.1(2) . . ? C7 O4 C8 114.7(2) . . ? H1A N1 H1B 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? N1 C1 H1D 109.6 . . ? N1 C1 H1E 109.6 . . ? N1 C1 C2 110.3(2) . . ? H1D C1 H1E 108.1 . . ? C2 C1 H1D 109.6 . . ? C2 C1 H1E 109.6 . . ? C1 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C1 C2 C3 111.2(2) . . ? H2A C2 H2B 108.0 . . ? C3 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C2 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C4 C3 C2 111.7(2) . . ? C4 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? F1 C4 C3 108.8(2) . . ? F1 C4 C5 106.4(2) . . ? F1 C4 C7 108.5(2) . . ? C3 C4 C5 114.6(2) . . ? C3 C4 C7 109.2(2) . . ? C7 C4 C5 109.1(2) . . ? O1 C5 O2 126.8(3) . . ? O1 C5 C4 122.9(3) . . ? O2 C5 C4 110.3(2) . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O4 125.8(2) . . ? O3 C7 C4 122.2(2) . . ? O4 C7 C4 111.8(2) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.91 2.32 3.226(2) 172.2 2_676 N1 H1B Cl1 0.91 2.30 3.169(2) 158.9 1_455 N1 H1C Cl1 0.91 2.31 3.160(2) 154.7 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C4 C5 O1 31.3(3) . . . . ? F1 C4 C5 O2 -148.9(2) . . . . ? F1 C4 C7 O3 -176.5(2) . . . . ? F1 C4 C7 O4 7.7(3) . . . . ? N1 C1 C2 C3 174.8(2) . . . . ? C1 C2 C3 C4 177.0(2) . . . . ? C2 C3 C4 F1 -66.2(3) . . . . ? C2 C3 C4 C5 174.9(2) . . . . ? C2 C3 C4 C7 52.2(3) . . . . ? C3 C4 C5 O1 151.6(3) . . . . ? C3 C4 C5 O2 -28.6(3) . . . . ? C3 C4 C7 O3 65.0(3) . . . . ? C3 C4 C7 O4 -110.8(2) . . . . ? C5 C4 C7 O3 -60.9(3) . . . . ? C5 C4 C7 O4 123.2(2) . . . . ? C6 O2 C5 O1 0.5(4) . . . . ? C6 O2 C5 C4 -179.3(2) . . . . ? C7 C4 C5 O1 -85.7(3) . . . . ? C7 C4 C5 O2 94.1(2) . . . . ? C8 O4 C7 O3 -2.2(4) . . . . ? C8 O4 C7 C4 173.4(2) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 0 1 0.1580 -1.0005 -0.0003 0.9997 -0.1132 -0.0550 -0.0020 1 0 -1 0.1580 1.0005 0.0003 -0.9997 0.1132 0.0550 0.0020 0 -1 0 0.0985 -0.0008 -0.9990 0.0010 -0.0046 -0.0026 0.1117 0 1 0 0.0985 0.0008 0.9990 -0.0010 0.0046 0.0026 -0.1117 0 0 1 0.0242 -0.0003 -0.0001 1.0009 -0.0290 0.0348 -0.0095 0 0 -1 0.0242 0.0003 0.0001 -1.0009 0.0290 -0.0348 0.0095 _iucr_refinement_instructions_details ; TITL 15srv065 in P-1 #2 REM reset to P-1 #2 CELL 0.71073 5.820976 6.487541 15.748505 100.7378 96.6255 94.6122 ZERR 2 0.000371 0.00051 0.001216 0.0067 0.0058 0.0059 LATT 1 SFAC C H Cl F N O UNIT 16 30 2 2 2 8 EQIV $1 -1+X,+Y,+Z EQIV $2 1-X,2-Y,1-Z L.S. 9 PLAN 5 TEMP -153.15 HTAB N1 Cl1_$1 HTAB N1 Cl1 HTAB N1 Cl1_$2 BOND $h CONF fmap 2 53 ACTA OMIT -2 56 OMIT 0 -1 6 OMIT -3 -2 4 WGHT 0.035 0.8 FVAR 8.08591 REM REM REM Cl1 3 0.75418 1.29673 0.51960 11.00000 0.01597 0.01425 0.03024 = 0.00499 0.00285 0.00124 F1 4 0.68307 0.98869 0.17917 11.00000 0.02105 0.02103 0.03176 = 0.00861 0.00146 -0.00638 O1 6 0.55946 0.76911 0.01629 11.00000 0.02949 0.04837 0.02880 = 0.00558 0.00774 0.00710 O2 6 0.18710 0.76201 0.04072 11.00000 0.02275 0.03191 0.02152 = 0.00814 0.00003 -0.00378 O3 6 0.35966 0.52046 0.19529 11.00000 0.03137 0.01605 0.03308 = 0.00794 -0.00201 -0.00380 O4 6 0.71770 0.68003 0.24970 11.00000 0.02896 0.01721 0.03721 = 0.00708 -0.00891 0.00370 N1 5 0.22167 1.17720 0.44695 11.00000 0.01717 0.01385 0.02716 = 0.00203 0.00427 0.00290 AFIX 137 H1a 2 0.22289 1.04776 0.46134 11.00000 -1.20000 H1b 2 0.10864 1.24605 0.47189 11.00000 -1.20000 H1c 2 0.36231 1.25303 0.46662 11.00000 -1.20000 AFIX 0 C1 1 0.17450 1.15230 0.35047 11.00000 0.02185 0.01918 0.02627 = 0.00251 0.00038 0.00595 AFIX 23 H1d 2 0.18309 1.29298 0.33448 11.00000 -1.20000 H1e 2 0.01570 1.08124 0.32955 11.00000 -1.20000 AFIX 0 C2 1 0.35012 1.02328 0.30724 11.00000 0.02138 0.01667 0.02291 = 0.00381 0.00165 0.00527 AFIX 23 H2a 2 0.35185 0.88815 0.32781 11.00000 -1.20000 H2b 2 0.50720 1.10086 0.32416 11.00000 -1.20000 AFIX 0 C3 1 0.29164 0.97854 0.20797 11.00000 0.02291 0.01590 0.02321 = 0.00485 0.00066 0.00470 AFIX 23 H3a 2 0.13797 0.89465 0.19101 11.00000 -1.20000 H3b 2 0.28147 1.11363 0.18781 11.00000 -1.20000 AFIX 0 C4 1 0.47370 0.85891 0.16362 11.00000 0.01650 0.01395 0.02553 = 0.00640 0.00054 -0.00270 C5 1 0.41507 0.79095 0.06354 11.00000 0.02593 0.01585 0.02350 = 0.00661 0.00223 0.00158 C6 1 0.10737 0.69482 -0.05202 11.00000 0.03485 0.03693 0.02158 = 0.00821 -0.00371 -0.00750 AFIX 137 H6a 2 0.17218 0.79776 -0.08352 11.00000 -1.50000 H6b 2 -0.06283 0.68484 -0.06201 11.00000 -1.50000 H6c 2 0.15899 0.55656 -0.07308 11.00000 -1.50000 AFIX 0 C7 1 0.51043 0.66310 0.20300 11.00000 0.02211 0.01618 0.02026 = 0.00258 0.00232 0.00347 C8 1 0.75462 0.51060 0.29698 11.00000 0.05491 0.02148 0.05272 = 0.01206 -0.02718 0.00688 AFIX 137 H8a 2 0.74655 0.37666 0.25540 11.00000 -1.50000 H8b 2 0.63416 0.50186 0.33518 11.00000 -1.50000 H8c 2 0.90801 0.53912 0.33222 11.00000 -1.50000 AFIX 0 HKLF 4 END ; ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_4d_14srv042 _database_code_depnum_ccdc_archive 'CCDC 1401920' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2014-02-20 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773) ; _chemical_name_common ? _chemical_name_systematic ; (rac)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate ; _chemical_formula_moiety 'C7 H10 F N O3' _chemical_formula_sum 'C7 H10 F N O3' _chemical_formula_weight 175.16 _chemical_melting_point ? _chemical_oxdiff_formula 'C7 H10 F1 N1 O3' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.2560(4) _cell_length_b 6.72544(17) _cell_length_c 10.4787(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.193(4) _cell_angle_gamma 90.00 _cell_volume 793.93(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4749 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.5790 _cell_measurement_theta_min 1.8150 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94438 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.17 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0236 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14038 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 3.53 _diffrn_ambient_temperature 120.0 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Agilent Xcalibur' _diffrn_measurement_method \w-scan _diffrn_orient_matrix_UB_11 0.0098259000 _diffrn_orient_matrix_UB_12 -0.0947619000 _diffrn_orient_matrix_UB_13 -0.0232601000 _diffrn_orient_matrix_UB_21 0.0160497000 _diffrn_orient_matrix_UB_22 0.0462023000 _diffrn_orient_matrix_UB_23 -0.0509704000 _diffrn_orient_matrix_UB_31 0.0600403000 _diffrn_orient_matrix_UB_32 0.0031482000 _diffrn_orient_matrix_UB_33 0.0478793000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_type 'sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2020 _reflns_number_total 2324 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.93 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.465 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0346 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.1900P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.0942 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.77798(6) 1.00559(10) 0.72182(6) 0.02313(16) Uani 1 d . . . O1 O 0.88589(7) 1.12138(10) 0.53344(8) 0.02062(17) Uani 1 d . . . O2 O 0.62666(6) 0.97186(10) 0.35850(7) 0.01704(16) Uani 1 d . . . O3 O 0.60288(7) 1.18044(12) 0.51438(8) 0.02513(19) Uani 1 d . . . N1 N 0.93017(7) 0.79229(12) 0.56406(9) 0.01582(17) Uani 1 d . . . C1 C 0.86321(8) 0.94999(14) 0.55960(10) 0.01408(18) Uani 1 d . . . C2 C 0.75183(8) 0.91935(14) 0.59126(9) 0.01446(18) Uani 1 d . . . C3 C 0.71776(9) 0.70253(15) 0.59688(11) 0.0192(2) Uani 1 d . . . C4 C 0.82841(9) 0.57784(16) 0.67313(11) 0.0189(2) Uani 1 d . . . C5 C 0.90752(9) 0.58519(14) 0.59288(11) 0.0174(2) Uani 1 d . . . C6 C 0.65139(8) 1.04246(14) 0.48597(10) 0.01509(19) Uani 1 d . . . C7 C 0.53792(10) 1.08278(18) 0.24668(11) 0.0235(2) Uani 1 d . . . H1 H 0.9892(14) 0.818(2) 0.5387(15) 0.028(4) Uiso 1 d . . . H3A H 0.6781(13) 0.651(2) 0.5013(15) 0.023(3) Uiso 1 d . . . H3B H 0.6619(14) 0.699(2) 0.6431(16) 0.031(4) Uiso 1 d . . . H4A H 0.8094(13) 0.442(2) 0.6855(15) 0.025(3) Uiso 1 d . . . H4B H 0.8707(13) 0.630(2) 0.7655(16) 0.027(4) Uiso 1 d . . . H5A H 0.8708(13) 0.515(2) 0.5032(15) 0.023(3) Uiso 1 d . . . H5B H 0.9843(14) 0.524(2) 0.6432(16) 0.026(4) Uiso 1 d . . . H7A H 0.4688(14) 1.107(2) 0.2659(15) 0.030(4) Uiso 1 d . . . H7B H 0.5707(15) 1.205(3) 0.2357(17) 0.037(4) Uiso 1 d . . . H7C H 0.5167(15) 0.999(2) 0.1637(17) 0.033(4) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0244(3) 0.0312(3) 0.0141(3) -0.0051(2) 0.0079(2) 0.0009(3) O1 0.0205(4) 0.0125(3) 0.0328(4) 0.0006(3) 0.0147(3) -0.0016(3) O2 0.0187(3) 0.0169(3) 0.0145(3) 0.0011(2) 0.0054(3) 0.0055(2) O3 0.0269(4) 0.0245(4) 0.0249(4) -0.0036(3) 0.0112(3) 0.0087(3) N1 0.0149(4) 0.0132(4) 0.0213(4) 0.0011(3) 0.0092(3) -0.0003(3) C1 0.0132(4) 0.0145(4) 0.0141(4) -0.0014(3) 0.0049(3) -0.0022(3) C2 0.0146(4) 0.0163(4) 0.0132(4) -0.0007(3) 0.0062(3) -0.0011(3) C3 0.0162(4) 0.0180(4) 0.0244(5) 0.0056(4) 0.0091(4) -0.0015(3) C4 0.0201(5) 0.0181(4) 0.0186(5) 0.0060(4) 0.0077(4) 0.0004(4) C5 0.0189(4) 0.0129(4) 0.0207(5) 0.0029(3) 0.0082(4) 0.0009(3) C6 0.0148(4) 0.0146(4) 0.0175(4) -0.0001(3) 0.0081(3) -0.0007(3) C7 0.0257(5) 0.0255(5) 0.0180(5) 0.0060(4) 0.0074(4) 0.0115(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.4020(11) . ? O1 C1 1.2414(12) . ? O2 C6 1.3352(12) . ? O2 C7 1.4521(12) . ? O3 C6 1.2011(12) . ? N1 C1 1.3305(12) . ? N1 C5 1.4746(12) . ? N1 H1 0.881(16) . ? C1 C2 1.5403(13) . ? C2 C3 1.5243(13) . ? C2 C6 1.5325(13) . ? C3 C4 1.5255(14) . ? C3 H3A 0.987(14) . ? C3 H3B 0.983(15) . ? C4 C5 1.5139(15) . ? C4 H4A 0.964(15) . ? C4 H4B 0.966(15) . ? C5 H5A 0.987(14) . ? C5 H5B 0.972(15) . ? C7 H7A 0.959(16) . ? C7 H7B 0.939(17) . ? C7 H7C 0.980(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C7 115.30(8) . . ? C1 N1 C5 126.65(8) . . ? C1 N1 H1 113.7(10) . . ? C5 N1 H1 119.3(10) . . ? O1 C1 N1 124.00(9) . . ? O1 C1 C2 117.79(8) . . ? N1 C1 C2 118.19(8) . . ? F1 C2 C1 105.87(7) . . ? F1 C2 C3 108.60(8) . . ? F1 C2 C6 106.80(8) . . ? C3 C2 C1 114.57(8) . . ? C3 C2 C6 112.96(8) . . ? C6 C2 C1 107.54(8) . . ? C2 C3 C4 110.22(8) . . ? C2 C3 H3A 109.2(8) . . ? C2 C3 H3B 107.3(9) . . ? C4 C3 H3A 108.7(8) . . ? C4 C3 H3B 112.1(9) . . ? H3A C3 H3B 109.3(12) . . ? C3 C4 H4A 112.3(9) . . ? C3 C4 H4B 109.9(9) . . ? C5 C4 C3 108.83(8) . . ? C5 C4 H4A 110.3(9) . . ? C5 C4 H4B 109.7(9) . . ? H4A C4 H4B 105.8(12) . . ? N1 C5 C4 110.97(8) . . ? N1 C5 H5A 107.9(8) . . ? N1 C5 H5B 107.1(9) . . ? C4 C5 H5A 111.2(9) . . ? C4 C5 H5B 112.3(9) . . ? H5A C5 H5B 107.2(12) . . ? O2 C6 C2 109.25(8) . . ? O3 C6 O2 125.68(9) . . ? O3 C6 C2 125.08(9) . . ? O2 C7 H7A 111.2(9) . . ? O2 C7 H7B 109.1(10) . . ? O2 C7 H7C 105.9(10) . . ? H7A C7 H7B 109.3(14) . . ? H7A C7 H7C 109.7(14) . . ? H7B C7 H7C 111.6(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.881(16) 1.998(16) 2.8770(11) 175.7(14) 3_776 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C2 C3 C4 -76.45(10) . . . . ? F1 C2 C6 O2 177.17(7) . . . . ? F1 C2 C6 O3 -2.89(13) . . . . ? O1 C1 C2 F1 -70.70(11) . . . . ? O1 C1 C2 C3 169.66(9) . . . . ? O1 C1 C2 C6 43.19(11) . . . . ? N1 C1 C2 F1 108.25(9) . . . . ? N1 C1 C2 C3 -11.39(12) . . . . ? N1 C1 C2 C6 -137.85(9) . . . . ? C1 N1 C5 C4 -23.07(14) . . . . ? C1 C2 C3 C4 41.65(11) . . . . ? C1 C2 C6 O2 63.90(10) . . . . ? C1 C2 C6 O3 -116.16(11) . . . . ? C2 C3 C4 C5 -62.56(11) . . . . ? C3 C2 C6 O2 -63.50(10) . . . . ? C3 C2 C6 O3 116.43(11) . . . . ? C3 C4 C5 N1 52.18(11) . . . . ? C5 N1 C1 O1 -179.27(9) . . . . ? C5 N1 C1 C2 1.85(14) . . . . ? C6 C2 C3 C4 165.27(8) . . . . ? C7 O2 C6 O3 3.87(15) . . . . ? C7 O2 C6 C2 -176.19(8) . . . . ? _iucr_refinement_instructions_details ; TITL 14srv042 in P2(1)/c CELL 0.71073 12.255998 6.725436 10.478718 90 113.1927 90 ZERR 4 0.000433 0.000169 0.000368 0 0.0041 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O F UNIT 28 40 4 12 4 EQIV $1 2-X,2-Y,1-Z L.S. 9 PLAN 5 HTAB N1 O1_$1 CONF BOND $h fmap 2 acta OMIT -2 60 OMIT 1 0 0 REM T:/People/DSY/14srv042/struct/14srv042.hkl WGHT 0.05 0.19 FVAR 8.88068 F1 5 0.77798 1.00559 0.72182 11.00000 0.02443 0.03123 0.01408 = -0.00505 0.00792 0.00093 O1 4 0.88589 1.12137 0.53343 11.00000 0.02054 0.01246 0.03277 = 0.00061 0.01467 -0.00157 O2 4 0.62666 0.97186 0.35850 11.00000 0.01870 0.01689 0.01452 = 0.00109 0.00543 0.00554 O3 4 0.60288 1.18044 0.51438 11.00000 0.02688 0.02454 0.02494 = -0.00363 0.01122 0.00871 N1 3 0.93017 0.79230 0.56406 11.00000 0.01489 0.01324 0.02133 = 0.00110 0.00925 -0.00030 C1 1 0.86321 0.94998 0.55960 11.00000 0.01318 0.01457 0.01408 = -0.00143 0.00490 -0.00223 C2 1 0.75184 0.91934 0.59126 11.00000 0.01460 0.01633 0.01321 = -0.00073 0.00625 -0.00108 C3 1 0.71776 0.70253 0.59688 11.00000 0.01623 0.01805 0.02440 = 0.00561 0.00914 -0.00151 C4 1 0.82841 0.57785 0.67313 11.00000 0.02010 0.01809 0.01861 = 0.00598 0.00773 0.00040 C5 1 0.90752 0.58518 0.59288 11.00000 0.01895 0.01288 0.02066 = 0.00294 0.00817 0.00090 C6 1 0.65139 1.04246 0.48598 11.00000 0.01480 0.01465 0.01751 = -0.00005 0.00813 -0.00075 C7 1 0.53792 1.08279 0.24668 11.00000 0.02571 0.02554 0.01805 = 0.00605 0.00738 0.01150 H1 2 0.98924 0.81789 0.53869 11.00000 0.02814 H3a 2 0.67816 0.65124 0.50136 11.00000 0.02289 H3b 2 0.66183 0.69899 0.64308 11.00000 0.03075 H4a 2 0.80933 0.44211 0.68543 11.00000 0.02541 H4b 2 0.87065 0.62998 0.76549 11.00000 0.02719 H5a 2 0.87075 0.51537 0.50319 11.00000 0.02312 H5b 2 0.98429 0.52357 0.64327 11.00000 0.02603 H7a 2 0.46883 1.10732 0.26593 11.00000 0.03022 H7b 2 0.57077 1.20460 0.23569 11.00000 0.03716 H7c 2 0.51676 0.99916 0.16377 11.00000 0.03353 HKLF 4 END ; ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_8_14srv004 _database_code_depnum_ccdc_archive 'CCDC 1401921' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2014-04-04 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'Cl, C7 H13 F N O4' _chemical_formula_sum 'C7 H13 Cl F N O4' _chemical_formula_weight 229.63 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.2350(7) _cell_length_b 11.3068(7) _cell_length_c 7.6415(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.2891(17) _cell_angle_gamma 90.00 _cell_volume 1040.12(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9971 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 31.54 _cell_measurement_theta_min 2.47 _exptl_absorpt_coefficient_mu 0.372 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0920 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.9261. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 21745 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.47 _diffrn_ambient_temperature 120.0 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Bruker D8 Venture' _diffrn_measurement_device_type D8Venture _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'ImuS microsource' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2721 _reflns_number_total 3038 _reflns_threshold_expression >2sigma(I) _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.586 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 179 _refine_ls_number_reflns 3038 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0341 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.0873 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl1 Cl 0.501476(19) 0.85721(2) 0.20873(3) 0.01750(9) Uani 1 d . . . F1 F 0.82834(5) 0.67909(5) 0.01818(8) 0.01878(14) Uani 1 d . . . O1 O 0.87659(6) 0.39998(7) 0.21097(11) 0.02117(17) Uani 1 d . . . O2 O 0.99028(7) 0.55145(7) 0.18471(12) 0.02671(19) Uani 1 d . . . O3 O 0.75641(6) 0.39687(7) -0.15572(9) 0.01785(16) Uani 1 d . . . O4 O 0.77481(6) 0.57242(7) -0.28658(10) 0.01928(16) Uani 1 d . . . N1 N 0.60238(9) 0.61344(9) 0.35824(13) 0.02004(19) Uani 1 d . . . C1 C 0.80051(8) 0.56142(8) 0.03289(12) 0.01301(18) Uani 1 d . . . C2 C 0.69467(8) 0.55431(9) 0.11183(12) 0.01387(18) Uani 1 d . . . C3 C 0.71079(9) 0.60942(10) 0.29601(13) 0.0188(2) Uani 1 d . . . C4 C 0.90168(8) 0.50422(9) 0.15045(12) 0.01393(18) Uani 1 d . . . C5 C 0.96777(10) 0.33852(11) 0.32313(18) 0.0257(2) Uani 1 d . . . C6 C 0.77742(8) 0.51151(9) -0.15736(13) 0.01372(18) Uani 1 d . . . C7 C 0.72684(11) 0.34234(11) -0.32981(16) 0.0251(2) Uani 1 d . . . H1A H 0.6123(13) 0.6254(14) 0.477(2) 0.030(4) Uiso 1 d . . . H1B H 0.5657(13) 0.5449(14) 0.333(2) 0.026(4) Uiso 1 d . . . H1C H 0.5637(14) 0.6708(15) 0.309(2) 0.032(4) Uiso 1 d . . . H2A H 0.6726(11) 0.4728(12) 0.1148(17) 0.016(3) Uiso 1 d . . . H2B H 0.6366(11) 0.5959(13) 0.0339(18) 0.017(3) Uiso 1 d . . . H3A H 0.7387(12) 0.6874(14) 0.2945(19) 0.024(4) Uiso 1 d . . . H3B H 0.7635(12) 0.5633(13) 0.3807(19) 0.021(3) Uiso 1 d . . . H5A H 0.9390(13) 0.2630(15) 0.351(2) 0.032(4) Uiso 1 d . . . H5B H 0.9948(16) 0.3867(17) 0.427(2) 0.047(5) Uiso 1 d . . . H5C H 1.0238(17) 0.3250(18) 0.263(3) 0.048(5) Uiso 1 d . . . H7A H 0.6624(14) 0.3808(14) -0.397(2) 0.030(4) Uiso 1 d . . . H7B H 0.7068(14) 0.2623(15) -0.308(2) 0.033(4) Uiso 1 d . . . H7C H 0.7868(15) 0.3470(14) -0.390(2) 0.032(4) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01823(13) 0.01942(14) 0.01470(13) 0.00247(8) 0.00256(9) 0.00198(8) F1 0.0233(3) 0.0114(3) 0.0204(3) 0.0033(2) 0.0003(2) -0.0027(2) O1 0.0160(3) 0.0167(4) 0.0280(4) 0.0093(3) -0.0036(3) -0.0009(3) O2 0.0159(4) 0.0208(4) 0.0401(5) 0.0061(3) -0.0041(3) -0.0038(3) O3 0.0223(4) 0.0166(3) 0.0138(3) -0.0025(3) 0.0009(3) -0.0011(3) O4 0.0193(4) 0.0244(4) 0.0140(3) 0.0045(3) 0.0028(3) 0.0017(3) N1 0.0291(5) 0.0159(4) 0.0172(4) -0.0002(3) 0.0096(4) 0.0031(4) C1 0.0150(4) 0.0106(4) 0.0128(4) 0.0015(3) 0.0005(3) -0.0010(3) C2 0.0154(4) 0.0151(4) 0.0108(4) -0.0006(3) 0.0013(3) 0.0009(3) C3 0.0223(5) 0.0204(5) 0.0132(4) -0.0033(4) 0.0022(4) -0.0005(4) C4 0.0150(4) 0.0136(4) 0.0129(4) 0.0000(3) 0.0015(3) 0.0005(3) C5 0.0214(5) 0.0201(5) 0.0319(6) 0.0097(5) -0.0055(5) 0.0037(4) C6 0.0105(4) 0.0170(4) 0.0135(4) 0.0001(3) 0.0017(3) 0.0013(3) C7 0.0301(6) 0.0257(6) 0.0177(5) -0.0077(4) -0.0005(4) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.3829(11) . ? O1 C4 1.3222(12) . ? O1 C5 1.4562(13) . ? O2 C4 1.1948(12) . ? O3 C6 1.3219(12) . ? O3 C7 1.4522(13) . ? O4 C6 1.1996(12) . ? N1 C3 1.4877(14) . ? N1 H1A 0.907(17) . ? N1 H1B 0.899(16) . ? N1 H1C 0.850(18) . ? C1 C2 1.5252(13) . ? C1 C4 1.5362(13) . ? C1 C6 1.5379(13) . ? C2 C3 1.5194(13) . ? C2 H2A 0.961(14) . ? C2 H2B 0.964(14) . ? C3 H3A 0.946(16) . ? C3 H3B 0.979(15) . ? C5 H5A 0.963(16) . ? C5 H5B 0.972(19) . ? C5 H5C 0.91(2) . ? C7 H7A 0.963(17) . ? C7 H7B 0.961(17) . ? C7 H7C 0.935(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C5 115.46(8) . . ? C6 O3 C7 115.13(8) . . ? C3 N1 H1A 111.0(10) . . ? C3 N1 H1B 110.3(10) . . ? C3 N1 H1C 109.8(11) . . ? H1A N1 H1B 108.2(14) . . ? H1A N1 H1C 107.3(15) . . ? H1B N1 H1C 110.2(14) . . ? F1 C1 C2 108.76(8) . . ? F1 C1 C4 105.56(7) . . ? F1 C1 C6 106.41(7) . . ? C2 C1 C4 113.51(8) . . ? C2 C1 C6 109.20(7) . . ? C4 C1 C6 113.02(8) . . ? C1 C2 H2A 108.7(8) . . ? C1 C2 H2B 108.3(8) . . ? C3 C2 C1 111.46(8) . . ? C3 C2 H2A 111.2(8) . . ? C3 C2 H2B 109.4(8) . . ? H2A C2 H2B 107.6(11) . . ? N1 C3 C2 109.45(9) . . ? N1 C3 H3A 108.6(9) . . ? N1 C3 H3B 109.0(9) . . ? C2 C3 H3A 111.0(9) . . ? C2 C3 H3B 110.8(8) . . ? H3A C3 H3B 107.9(12) . . ? O1 C4 C1 111.51(8) . . ? O2 C4 O1 125.46(9) . . ? O2 C4 C1 123.01(9) . . ? O1 C5 H5A 106.4(10) . . ? O1 C5 H5B 109.1(11) . . ? O1 C5 H5C 110.5(12) . . ? H5A C5 H5B 113.6(14) . . ? H5A C5 H5C 107.7(16) . . ? H5B C5 H5C 109.5(17) . . ? O3 C6 C1 110.73(8) . . ? O4 C6 O3 126.45(9) . . ? O4 C6 C1 122.74(9) . . ? O3 C7 H7A 109.9(10) . . ? O3 C7 H7B 105.5(10) . . ? O3 C7 H7C 109.8(10) . . ? H7A C7 H7B 108.0(14) . . ? H7A C7 H7C 110.6(14) . . ? H7B C7 H7C 112.8(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.907(17) 2.421(17) 3.1605(9) 138.9(13) 4_576 N1 H1A O4 0.907(17) 2.506(16) 3.1602(13) 129.3(13) 1_556 N1 H1B Cl1 0.899(16) 2.278(16) 3.1682(10) 170.8(13) 2_645 N1 H1C Cl1 0.850(18) 2.324(18) 3.1499(10) 164.0(15) . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C3 -60.80(10) . . . . ? F1 C1 C4 O1 164.51(8) . . . . ? F1 C1 C4 O2 -13.61(13) . . . . ? F1 C1 C6 O3 176.27(7) . . . . ? F1 C1 C6 O4 -6.73(12) . . . . ? C1 C2 C3 N1 173.26(8) . . . . ? C2 C1 C4 O1 45.49(11) . . . . ? C2 C1 C4 O2 -132.63(10) . . . . ? C2 C1 C6 O3 -66.50(10) . . . . ? C2 C1 C6 O4 110.50(10) . . . . ? C4 C1 C2 C3 56.37(11) . . . . ? C4 C1 C6 O3 60.87(10) . . . . ? C4 C1 C6 O4 -122.13(10) . . . . ? C5 O1 C4 O2 -2.31(16) . . . . ? C5 O1 C4 C1 179.63(9) . . . . ? C6 C1 C2 C3 -176.53(8) . . . . ? C6 C1 C4 O1 -79.59(10) . . . . ? C6 C1 C4 O2 102.30(11) . . . . ? C7 O3 C6 O4 -0.41(14) . . . . ? C7 O3 C6 C1 176.45(9) . . . . ? _iucr_refinement_instructions_details ; TITL 14srv004 in P21/c #14 CELL 0.71073 12.235 11.3068 7.6415 90 100.2891 90 ZERR 4 0.0007 0.0007 0.0004 0 0.0017 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O F Cl UNIT 28 52 4 16 4 4 EQIV $1 1-X,-0.5+Y,0.5-Z EQIV $2 +X,1.5-Y,0.5+Z EQIV $3 +X,+Y,1+Z L.S. 9 PLAN 5 HTAB N1 Cl1 HTAB N1 Cl1_$1 HTAB N1 Cl1_$2 HTAB N1 O4_$3 CONF REM reset to P21/c #14 BOND $h fmap 2 53 acta OMIT -2 60 OMIT 0 2 1 REM D:/Struc/14S/14srv104/14srv004.hkl WGHT 0.05 0.17 FVAR 0.21237 Cl1 6 0.50148 0.85721 0.20873 11.00000 0.01823 0.01942 0.01470 = 0.00247 0.00256 0.00198 F1 5 0.82834 0.67909 0.01818 11.00000 0.02332 0.01136 0.02036 = 0.00334 0.00034 -0.00274 O1 4 0.87658 0.39998 0.21097 11.00000 0.01598 0.01675 0.02801 = 0.00930 -0.00360 -0.00089 O2 4 0.99028 0.55145 0.18471 11.00000 0.01592 0.02081 0.04005 = 0.00611 -0.00406 -0.00379 O3 4 0.75641 0.39687 -0.15572 11.00000 0.02231 0.01657 0.01382 = -0.00249 0.00093 -0.00113 O4 4 0.77480 0.57242 -0.28658 11.00000 0.01933 0.02442 0.01401 = 0.00450 0.00276 0.00167 N1 3 0.60237 0.61344 0.35824 11.00000 0.02907 0.01585 0.01721 = -0.00016 0.00963 0.00307 C1 1 0.80051 0.56142 0.03289 11.00000 0.01496 0.01055 0.01279 = 0.00147 0.00051 -0.00096 C2 1 0.69467 0.55431 0.11183 11.00000 0.01536 0.01513 0.01075 = -0.00064 0.00134 0.00087 C3 1 0.71079 0.60942 0.29601 11.00000 0.02230 0.02044 0.01321 = -0.00328 0.00221 -0.00047 C4 1 0.90168 0.50422 0.15045 11.00000 0.01499 0.01357 0.01286 = 0.00002 0.00148 0.00049 C5 1 0.96777 0.33852 0.32314 11.00000 0.02145 0.02010 0.03187 = 0.00965 -0.00549 0.00375 C6 1 0.77742 0.51151 -0.15736 11.00000 0.01047 0.01704 0.01349 = 0.00006 0.00175 0.00133 C7 1 0.72684 0.34234 -0.32981 11.00000 0.03015 0.02566 0.01774 = -0.00770 -0.00054 -0.00006 H1a 2 0.61233 0.62537 0.47741 11.00000 0.03004 H1b 2 0.56567 0.54493 0.33336 11.00000 0.02574 H1c 2 0.56369 0.67079 0.30879 11.00000 0.03205 H2a 2 0.67264 0.47283 0.11480 11.00000 0.01580 H2b 2 0.63659 0.59585 0.03394 11.00000 0.01697 H3a 2 0.73868 0.68737 0.29454 11.00000 0.02401 H3b 2 0.76352 0.56330 0.38070 11.00000 0.02117 H5a 2 0.93904 0.26296 0.35119 11.00000 0.03204 H5b 2 0.99483 0.38669 0.42715 11.00000 0.04677 H5c 2 1.02384 0.32503 0.26257 11.00000 0.04771 H7a 2 0.66239 0.38078 -0.39672 11.00000 0.02983 H7b 2 0.70681 0.26227 -0.30760 11.00000 0.03272 H7c 2 0.78675 0.34701 -0.39017 11.00000 0.03237 HKLF 4 END ; ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_9_14srv109 _database_code_depnum_ccdc_archive 'CCDC 1401922' _audit_update_record ; 2015-05-20 deposited with the CCDC. 2015-10-13 downloaded from the CCDC. ; _audit_creation_date 2014-04-11 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _chemical_name_common ? _chemical_name_systematic ; methyl 3-fluoro-2-oxo-3-pyrrolidinecarboxylate ; _chemical_formula_moiety 'C6 H8 F N O3, H2 O' _chemical_formula_sum 'C6 H10 F N O4' _chemical_formula_weight 179.15 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.5648(7) _cell_length_b 6.6759(7) _cell_length_c 9.6206(10) _cell_angle_alpha 98.163(3) _cell_angle_beta 100.929(3) _cell_angle_gamma 101.047(3) _cell_volume 399.30(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3503 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 31.57 _cell_measurement_theta_min 3.16 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1445 before and 0.0996 after correction. The Ratio of minimum to maximum transmission is 0.6623. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 188 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_unetI/netI 0.0681 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6012 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 3.16 _diffrn_ambient_temperature 120.0 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device 'Bruker D8 Venture' _diffrn_measurement_device_type D8Venture _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe X-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'ImuS microsource' _diffrn_special_details ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 1877 _reflns_number_total 2317 _reflns_threshold_expression >2sigma(I) _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.543 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.095 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0548 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1404 _refine_ls_wR_factor_ref 0.1501 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn F1 F 0.38979(12) 0.50223(13) 0.16612(9) 0.0208(2) Uani 1 d . . . O1 O 0.66817(16) 0.85861(15) 0.12521(11) 0.0210(3) Uani 1 d . . . O2 O 0.43275(16) 0.69399(15) 0.43221(11) 0.0209(3) Uani 1 d . . . O3 O 0.79024(15) 0.75684(15) 0.46786(10) 0.0185(2) Uani 1 d . . . N1 N 0.90694(19) 0.64960(18) 0.16237(13) 0.0167(3) Uani 1 d . . . C1 C 0.7281(2) 0.7094(2) 0.16881(14) 0.0151(3) Uani 1 d . . . C2 C 0.5981(2) 0.5627(2) 0.24550(14) 0.0150(3) Uani 1 d . . . C3 C 0.7081(2) 0.3817(2) 0.24868(16) 0.0180(3) Uani 1 d . . . C4 C 0.9326(2) 0.4703(2) 0.22986(16) 0.0184(3) Uani 1 d . . . C5 C 0.5925(2) 0.67779(19) 0.39273(14) 0.0146(3) Uani 1 d . . . C6 C 0.8084(3) 0.8764(2) 0.60989(16) 0.0210(3) Uani 1 d . . . H1 H 1.007(3) 0.719(3) 0.132(2) 0.028(5) Uiso 1 d . . . H3A H 0.707(3) 0.330(3) 0.335(2) 0.036(5) Uiso 1 d . . . H3B H 0.628(3) 0.276(3) 0.167(2) 0.026(5) Uiso 1 d . . . H4A H 1.038(3) 0.510(3) 0.324(2) 0.023(4) Uiso 1 d . . . H4B H 0.987(3) 0.369(3) 0.169(2) 0.028(5) Uiso 1 d . . . H6A H 0.750(4) 0.793(3) 0.668(2) 0.036(5) Uiso 1 d . . . H6B H 0.960(3) 0.921(3) 0.646(2) 0.023(4) Uiso 1 d . . . H6C H 0.744(3) 0.994(3) 0.600(2) 0.026(5) Uiso 1 d . . . O4 O 0.23967(17) 0.91176(17) 0.08602(13) 0.0218(3) Uani 1 d . . . H4C H 0.362(4) 0.882(3) 0.102(3) 0.040(6) Uiso 1 d . . . H4D H 0.239(4) 0.981(3) 0.020(3) 0.041(6) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0130(4) 0.0271(5) 0.0185(4) 0.0011(3) 0.0007(3) 0.0002(3) O1 0.0237(6) 0.0227(5) 0.0214(5) 0.0106(4) 0.0073(4) 0.0094(4) O2 0.0181(5) 0.0258(5) 0.0213(5) 0.0036(4) 0.0077(4) 0.0083(4) O3 0.0171(5) 0.0212(5) 0.0151(5) -0.0009(4) 0.0029(4) 0.0031(4) N1 0.0146(6) 0.0200(6) 0.0168(6) 0.0051(4) 0.0060(4) 0.0034(4) C1 0.0150(6) 0.0178(6) 0.0115(6) 0.0013(5) 0.0023(5) 0.0027(5) C2 0.0127(6) 0.0174(6) 0.0138(6) 0.0022(5) 0.0021(5) 0.0021(4) C3 0.0202(7) 0.0157(6) 0.0190(7) 0.0027(5) 0.0065(5) 0.0043(5) C4 0.0178(7) 0.0191(6) 0.0195(7) 0.0037(5) 0.0045(5) 0.0064(5) C5 0.0172(6) 0.0130(6) 0.0156(6) 0.0054(5) 0.0050(5) 0.0049(5) C6 0.0263(8) 0.0197(7) 0.0150(7) -0.0001(5) 0.0019(6) 0.0056(6) O4 0.0188(5) 0.0262(5) 0.0245(6) 0.0121(4) 0.0082(4) 0.0064(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.3858(15) . ? O1 C1 1.2369(16) . ? O2 C5 1.1995(16) . ? O3 C5 1.3264(16) . ? O3 C6 1.4528(17) . ? N1 C1 1.3196(17) . ? N1 C4 1.4626(18) . ? N1 H1 0.85(2) . ? C1 C2 1.5348(19) . ? C2 C3 1.5230(18) . ? C2 C5 1.5228(18) . ? C3 C4 1.534(2) . ? C3 H3A 0.95(2) . ? C3 H3B 0.966(19) . ? C4 H4A 0.993(19) . ? C4 H4B 0.994(19) . ? C6 H6A 0.92(2) . ? C6 H6B 0.962(19) . ? C6 H6C 0.967(19) . ? O4 H4C 0.86(2) . ? O4 H4D 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O3 C6 115.04(11) . . ? C1 N1 C4 114.51(12) . . ? C1 N1 H1 122.9(13) . . ? C4 N1 H1 122.1(13) . . ? O1 C1 N1 128.40(13) . . ? O1 C1 C2 123.06(12) . . ? N1 C1 C2 108.53(11) . . ? F1 C2 C1 108.65(10) . . ? F1 C2 C3 112.29(10) . . ? F1 C2 C5 107.01(10) . . ? C3 C2 C1 103.90(10) . . ? C5 C2 C1 109.85(10) . . ? C5 C2 C3 115.00(11) . . ? C2 C3 C4 104.54(11) . . ? C2 C3 H3A 110.7(12) . . ? C2 C3 H3B 106.0(11) . . ? C4 C3 H3A 113.5(13) . . ? C4 C3 H3B 111.4(11) . . ? H3A C3 H3B 110.3(16) . . ? N1 C4 C3 103.39(11) . . ? N1 C4 H4A 112.4(11) . . ? N1 C4 H4B 111.3(11) . . ? C3 C4 H4A 111.6(11) . . ? C3 C4 H4B 112.8(11) . . ? H4A C4 H4B 105.6(15) . . ? O2 C5 O3 126.21(12) . . ? O2 C5 C2 124.53(12) . . ? O3 C5 C2 109.25(11) . . ? O3 C6 H6A 110.7(12) . . ? O3 C6 H6B 102.9(11) . . ? O3 C6 H6C 109.4(11) . . ? H6A C6 H6B 109.6(17) . . ? H6A C6 H6C 112.6(17) . . ? H6B C6 H6C 111.3(15) . . ? H4C O4 H4D 106(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.85(2) 1.96(2) 2.8076(16) 171.8(17) 1_655 O4 H4C O1 0.86(2) 2.02(2) 2.8635(15) 170(2) . O4 H4D O1 0.84(3) 1.99(3) 2.8002(15) 162(2) 2_675 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 F1 48.39(16) . . . . ? O2 C5 C2 F1 5.66(17) . . . . ? O3 C5 C2 F1 -173.84(9) . . . . ? N1 C1 C2 F1 -132.86(11) . . . . ? C1 C2 C3 C4 21.19(13) . . . . ? C1 C2 C5 O2 123.44(13) . . . . ? C1 C2 C5 O3 -56.07(13) . . . . ? C2 C1 N1 C4 -1.14(15) . . . . ? C2 C3 C4 N1 -21.72(14) . . . . ? C3 C2 C1 O1 168.12(12) . . . . ? C3 C2 C1 N1 -13.13(14) . . . . ? C3 C2 C5 O2 -119.81(14) . . . . ? C3 C2 C5 O3 60.68(14) . . . . ? C3 C4 N1 C1 14.78(15) . . . . ? C4 N1 C1 O1 177.53(13) . . . . ? C4 C3 C2 F1 138.42(11) . . . . ? C4 C3 C2 C5 -98.90(13) . . . . ? C5 C2 C1 O1 -68.36(15) . . . . ? C5 C2 C1 N1 110.39(12) . . . . ? _iucr_refinement_instructions_details ; TITL 14srv109 in P-1 #2 CELL 0.71073 6.5648 6.6759 9.6206 98.1632 100.9289 101.0472 ZERR 2 0.0007 0.0007 0.001 0.0034 0.0033 0.0034 LATT 1 SFAC C H F N O UNIT 12 20 2 2 8 EQIV $1 1-X,2-Y,-Z EQIV $2 1+X,+Y,+Z L.S. 9 PLAN 5 TEMP -153.15 HTAB O4 O1 HTAB O4 O1_$1 HTAB N1 O4_$2 CONF C4 N1 C1 O1 CONF C2 C1 N1 C4 CONF O1 C1 C2 F1 CONF N1 C1 C2 F1 CONF C3 C2 C1 O1 CONF C3 C2 C1 N1 CONF C5 C2 C1 O1 CONF C5 C2 C1 N1 CONF C4 C3 C2 F1 CONF C1 C2 C3 C4 CONF C4 C3 C2 C5 CONF C2 C3 C4 N1 CONF C3 C4 N1 C1 CONF O2 C5 C2 F1 CONF C1 C2 C5 O2 CONF C3 C2 C5 O2 CONF O3 C5 C2 F1 CONF C1 C2 C5 O3 CONF C3 C2 C5 O3 REM reset to P-1 #2 BOND $h fmap 2 53 acta OMIT -2 60 OMIT 0 0 1 OMIT 0 -2 2 REM D:/Struc/14S/14srv109/14srv109.hkl WGHT 0.09 0.04 FVAR 0.42513 F1 3 0.38979 0.50223 0.16612 11.00000 0.01303 0.02709 0.01845 = 0.00111 0.00067 0.00021 O1 5 0.66817 0.85861 0.12521 11.00000 0.02366 0.02265 0.02137 = 0.01055 0.00733 0.00943 O2 5 0.43275 0.69399 0.43221 11.00000 0.01805 0.02584 0.02134 = 0.00364 0.00771 0.00826 O3 5 0.79024 0.75684 0.46786 11.00000 0.01708 0.02122 0.01514 = -0.00092 0.00288 0.00306 N1 4 0.90694 0.64960 0.16237 11.00000 0.01465 0.02002 0.01676 = 0.00511 0.00598 0.00343 C1 1 0.72810 0.70935 0.16881 11.00000 0.01505 0.01775 0.01147 = 0.00125 0.00226 0.00271 C2 1 0.59805 0.56270 0.24550 11.00000 0.01268 0.01744 0.01375 = 0.00217 0.00212 0.00207 C3 1 0.70810 0.38170 0.24868 11.00000 0.02024 0.01572 0.01899 = 0.00268 0.00654 0.00429 C4 1 0.93258 0.47029 0.22986 11.00000 0.01778 0.01907 0.01954 = 0.00366 0.00454 0.00643 C5 1 0.59251 0.67779 0.39273 11.00000 0.01718 0.01295 0.01556 = 0.00538 0.00497 0.00493 C6 1 0.80835 0.87638 0.60989 11.00000 0.02632 0.01968 0.01502 = -0.00005 0.00190 0.00562 H1 2 1.00699 0.71918 0.13235 11.00000 0.02765 H3A 2 0.70693 0.33041 0.33541 11.00000 0.03573 H3B 2 0.62829 0.27590 0.16711 11.00000 0.02631 H4A 2 1.03778 0.50960 0.32357 11.00000 0.02344 H4B 2 0.98691 0.36912 0.16881 11.00000 0.02771 H6A 2 0.74979 0.79311 0.66771 11.00000 0.03635 H6B 2 0.95992 0.92062 0.64641 11.00000 0.02342 H6C 2 0.74385 0.99378 0.60034 11.00000 0.02556 O4 5 0.23967 0.91177 0.08602 11.00000 0.01879 0.02619 0.02446 = 0.01214 0.00816 0.00637 H4C 2 0.36203 0.88184 0.10184 11.00000 0.04027 H4D 2 0.23878 0.98120 0.02012 11.00000 0.04069 HKLF 4 END ;