# 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.
#
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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
;