data_14srv109 _audit_creation_date 2014-04-11 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _publ_contact_author_address ; Durham University Chemistry Science site South Rd Durham DH1 3LE UK ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Yufit, D.S.' _publ_contact_author_phone '' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _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 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) . . . . ?