#------------------------------------------------------------------------------ #$Date: 2020-05-02 09:49:23 +0300 (Sat, 02 May 2020) $ #$Revision: 251394 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557986.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557986 loop_ _publ_author_name 'Aakeroy, Christer B.' 'Bahra, Gurmit S.' 'Brown, Chris R.' 'Hitchcock, Peter B.' 'Patell, Yasmin' 'Seddon, Kenneth R.' _publ_section_title ; L-Proline 2,5-Dihydroxybenzoic Acid (1/1): A Zwitterion Co-crystal ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 762 _journal_page_last 767 _journal_paper_doi 10.3891/acta.chem.scand.49-0762 _journal_volume 49 _journal_year 1995 _chemical_formula_moiety 'C7 H6 O4, C5 H9 N O2' _chemical_formula_sum 'C12 H15 N O6' _chemical_formula_weight 269.25 _chemical_name_common ; L-Proline 2,5-Dihydroxybenzoic Acid (1/1) ; _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 5.896(2) _cell_length_b 11.486(1) _cell_length_c 18.016(3) _cell_volume 1220.1(5) _diffrn_ambient_temperature 130 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _exptl_absorpt_coefficient_mu 0.110 _exptl_crystal_density_diffrn 1.470 _exptl_crystal_F_000 568 _refine_ls_number_parameters 217 _refine_ls_number_reflns 973 _refine_ls_R_factor_gt 0.039 _refine_ls_wR_factor_gt 0.044 _cod_data_source_file Acta-Chem-Scand-1995-49-762.cif _cod_data_source_block 1 _cod_depositor_comments ; Said to be low temperature cold dinitrogen stream however, T(K) never given - arbitrarily fixed at 130 K... Thermal parameters for H atoms fixed at U = 0.04 ; _cod_database_code 1557986 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uiso 0.2703(4) 0.8058(2) 0.54140(10) 1.000 0.0320(10) . . . . O2 O Uiso -0.0300(5) 0.8498(2) 0.61050(10) 1.000 0.0400(10) . . . . O3 O Uiso -0.2217(4) 0.6874(2) 0.6889(2) 1.000 0.047(2) . . . . O4 O Uiso 0.4965(5) 0.4017(2) 0.61760(10) 1.000 0.0360(10) . . . . C1 C Uiso 0.1273(6) 0.6603(3) 0.6208(2) 1.000 0.026(2) . . . . C2 C Uiso -0.0429(6) 0.6204(3) 0.6677(2) 1.000 0.032(2) . . . . C3 C Uiso -0.0306(7) 0.5071(3) 0.6953(2) 1.000 0.035(2) . . . . C4 C Uiso 0.1499(7) 0.4365(3) 0.6783(2) 1.000 0.030(2) . . . . C5 C Uiso 0.3229(6) 0.4760(3) 0.6318(2) 1.000 0.026(2) . . . . O5 O Uiso 0.2388(4) 0.0191(2) 0.50230(10) 1.000 0.0280(10) . . . . C6 C Uiso 0.3115(6) 0.5879(3) 0.6030(2) 1.000 0.023(2) . . . . O6 O Uiso 0.4474(4) 0.1795(2) 0.48850(10) 1.000 0.0310(10) . . . . C7 C Uiso 0.1154(6) 0.7793(3) 0.5905(2) 1.000 0.027(2) . . . . N N Uiso 0.8007(5) 0.1046(2) 0.56390(10) 1.000 0.0240(10) . . . . C8 C Uiso 0.5962(6) 0.0266(3) 0.5623(2) 1.000 0.023(2) . . . . C9 C Uiso 0.5207(6) 0.0193(3) 0.6446(2) 1.000 0.028(2) . . . . C10 C Uiso 0.6069(7) 0.1318(3) 0.6778(2) 1.000 0.033(2) . . . . C11 C Uiso 0.8385(7) 0.1452(3) 0.6429(2) 1.000 0.035(2) . . . . C12 C Uiso 0.4165(6) 0.0820(3) 0.5131(2) 1.000 0.023(2) . . . . H3 H Uiso -0.158(8) 0.480(4) 0.723(2) 1.000 0.0400 . . . . H(O1) H Uiso 0.257(8) 0.894(4) 0.533(3) 1.000 0.0400 . . . . H4 H Uiso 0.162(7) 0.358(4) 0.702(2) 1.000 0.0400 . . . . H(O3) H Uiso -0.175(8) 0.760(4) 0.666(3) 1.000 0.0400 . . . . H(O4) H Uiso 0.593(8) 0.432(4) 0.587(2) 1.000 0.0400 . . . . H6 H Uiso 0.444(7) 0.615(4) 0.581(2) 1.000 0.0400 . . . . H(NA) H Uiso 0.767(7) 0.172(4) 0.526(2) 1.000 0.0400 . . . . H(NB) H Uiso 0.923(7) 0.066(4) 0.544(2) 1.000 0.0400 . . . . H8 H Uiso 0.634(7) -0.048(4) 0.542(2) 1.000 0.0400 . . . . H9A H Uiso 0.591(8) -0.049(4) 0.668(2) 1.000 0.0400 . . . . H9B H Uiso 0.341(8) 0.009(4) 0.646(2) 1.000 0.0400 . . . . H10A H Uiso 0.619(7) 0.136(4) 0.732(2) 1.000 0.0400 . . . . H10B H Uiso 0.511(8) 0.197(4) 0.663(2) 1.000 0.0400 . . . . H11A H Uiso 0.899(8) 0.227(4) 0.638(2) 1.000 0.0400 . . . . H11B H Uiso 0.967(9) 0.096(4) 0.663(2) 1.000 0.0400 . . . . 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' 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H(O1) 106(3) . . . no C2 O3 H(O3) 99(3) . . . no C5 O4 H(O4) 111(3) . . . no C6 C1 C7 120.1(3) . . . no C2 C1 C6 120.1(3) . . . no C2 C1 C7 119.8(3) . . . no O3 C2 C3 117.9(3) . . . yes O3 C2 C1 123.0(3) . . . yes C1 C2 C3 119.1(3) . . . no C2 C3 C4 120.8(3) . . . no C3 C4 C5 120.6(3) . . . no C4 C5 C6 119.4(3) . . . no O4 C5 C4 117.4(3) . . . yes O4 C5 C6 123.3(3) . . . yes C1 C6 C5 120.0(3) . . . no O1 C7 O2 122.0(3) . . . yes O1 C7 C1 115.7(3) . . . yes O2 C7 C1 122.3(3) . . . yes C8 N C11 108.7(2) . . . yes C4 C3 H3 122(3) . . . no C2 C3 H3 117(3) . . . no C3 C4 H4 120(2) . . . no C5 C4 H4 120(2) . . . no C1 C6 H6 123(3) . . . no C5 C6 H6 115(3) . . . no C8 N H(NB) 110(3) . . . no C11 N H(NA) 114(2) . . . no C8 N H(NA) 106(2) . . . no H(NA) N H(NB) 105(3) . . . no C11 N H(NB) 114(2) . . . no N C8 C12 108.7(3) . . . yes N C8 C9 104.1(3) . . . yes C9 C8 C12 112.3(3) . . . no C8 C9 C10 103.6(3) . . . no C9 C10 C11 103.1(3) . . . no N C11 C10 103.1(3) . . . yes O5 C12 C8 114.9(3) . . . yes O6 C12 C8 119.5(3) . . . yes O5 C12 O6 125.6(3) . . . yes N C8 H8 111(2) . . . no C9 C8 H8 113(2) . . . no C12 C8 H8 108(2) . . . no C8 C9 H9A 109(2) . . . no C8 C9 H9B 108(2) . . . no C10 C9 H9A 112(3) . . . no C10 C9 H9B 115(2) . . . no H9A C9 H9B 109(4) . . . no C9 C10 H10A 117(3) . . . no C9 C10 H10B 111(3) . . . no C11 C10 H10A 110(2) . . . no C11 C10 H10B 109(3) . . . no H10A C10 H10B 106(3) . . . no N C11 H11A 105(2) . . . no N C11 H11B 106(2) . . . no C10 C11 H11A 117(3) . . . no C10 C11 H11B 118(3) . . . no H11A C11 H11B 107(4) . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.307(4) . . yes O2 C7 1.233(4) . . yes O3 C2 1.360(4) . . yes O4 C5 1.357(4) . . yes O1 H(O1) 1.03(5) . . no O3 H(O3) 0.97(5) . . no O4 H(O4) 0.87(4) . . no C1 C7 1.474(5) . . no C1 C2 1.390(5) . . no C1 C6 1.405(5) . . no C2 C3 1.395(5) . . no C3 C4 1.373(6) . . no C4 C5 1.396(5) . . no C5 C6 1.388(5) . . no O5 C12 1.288(4) . . yes O6 C12 1.218(4) . . yes N C8 1.502(4) . . yes N C11 1.514(4) . . yes C3 H3 0.95(4) . . no C4 H4 1.00(4) . . no C6 H6 0.93(4) . . no N H(NA) 1.05(4) . . no N H(NB) 0.92(4) . . no C8 C9 1.550(5) . . no C8 C12 1.521(5) . . no C9 C10 1.512(5) . . no C10 C11 1.511(6) . . no C8 H8 0.96(4) . . no C9 H9A 0.98(4) . . no C9 H9B 1.07(5) . . no C10 H10A 0.98(4) . . no C10 H10B 0.98(5) . . no C11 H11A 1.01(5) . . no C11 H11B 1.01(5) . . no 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 _geom_hbond_publ_flag N H(NA) O6 1.05(4) 2.00(4) 2.631(4) 115(3) . yes N H(NA) O6 1.05(4) 2.03(4) 2.791(3) 127(3) 3_556 yes N H(NB) O5 0.92(4) 2.08(4) 2.978(4) 166(4) 1_655 yes O1 H(O1) O5 1.03(5) 1.54(5) 2.556(3) 168(5) 1_565 yes O3 H(O3) O2 0.97(5) 1.67(5) 2.599(4) 158(4) . yes O4 H(O4) O5 0.87(4) 1.91(4) 2.745(3) 162(4) 3_556 yes C10 H10B O4 0.98(5) 2.49(5) 3.348(4) 147(4) . yes C11 H11A O6 1.01(5) 2.54(4) 3.173(4) 121(3) 3_556 yes 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 C6 C1 C2 O3 177.9(3) . . . . no C6 C1 C2 C3 -1.4(5) . . . . no C7 C1 C2 O3 -1.4(5) . . . . no C7 C1 C2 C3 179.3(3) . . . . no C2 C1 C6 C5 0.5(5) . . . . no C7 C1 C6 C5 179.8(3) . . . . no C2 C1 C7 O1 -173.7(3) . . . . no C2 C1 C7 O2 6.9(5) . . . . no C6 C1 C7 O1 7.1(5) . . . . no C6 C1 C7 O2 -172.4(3) . . . . no O3 C2 C3 C4 -177.5(3) . . . . no C1 C2 C3 C4 1.8(5) . . . . no C2 C3 C4 C5 -1.3(6) . . . . no C3 C4 C5 O4 179.8(3) . . . . no C3 C4 C5 C6 0.3(6) . . . . no O4 C5 C6 C1 -179.4(3) . . . . no C4 C5 C6 C1 0.1(5) . . . . no C11 N C8 C9 -2.1(3) . . . . no C11 N C8 C12 117.8(3) . . . . no C8 N C11 C10 -22.9(3) . . . . no N C8 C9 C10 26.3(3) . . . . no C12 C8 C9 C10 -91.1(3) . . . . no N C8 C12 O5 174.7(3) . . . . no N C8 C12 O6 -6.4(4) . . . . no C9 C8 C12 O5 -70.6(4) . . . . no C9 C8 C12 O6 108.4(4) . . . . no C8 C9 C10 C11 -40.8(3) . . . . no C9 C10 C11 N 39.1(3) . . . . no