#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:30:04 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301811 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/06/4000699.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_4000699 loop_ _publ_author_name 'Keith Prout' 'Stephen J. Heyes' 'Christopher M. Dobson' 'Andrew McDaid' 'Thierry Maris' 'Matthias Muller' 'Matthew J. Seaman' _publ_section_title ; Variable-Temperature Studies of Order/Disorder Transitions in the Thiourea Pyridinium Halide Crystals by XRD and Solid-State 2H NMR ; _journal_name_full 'Chemistry of Material' _journal_page_first 3561 _journal_page_last 3569 _journal_paper_doi 10.1021/cm0001612 _journal_volume 12 _journal_year 2000 _chemical_formula_sum 'C7 H14 Br N5 S2' _chemical_formula_weight 312.25 _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P -2n 2a' _symmetry_space_group_name_H-M 'P 21 c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.431(2) _cell_length_b 10.984(2) _cell_length_c 8.291(5) _cell_measurement_temperature 100(2) _cell_volume 1314.2(8) _diffrn_ambient_temperature 100(2) _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1597 _diffrn_reflns_theta_max 75.0 _diffrn_reflns_theta_min 5.1 _exptl_absorpt_coefficient_mu 7.07 _exptl_crystal_density_diffrn 1.578 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1400 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0347 _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0500 _reflns_number_gt 1400 _reflns_number_total 1400 _reflns_threshold_expression >3sigma(I) _cod_data_source_file deposit.cif _cod_data_source_block Bromo_3 _cod_original_sg_symbol_H-M P21cn _cod_database_code 4000699 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,-y,-z 1/2+x,1/2+y,1/2-z x,1/2-y,1/2+z 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 N9 N -0.3575(3) 0.8339(3) -0.5762(5) 0.0273(12) Uani C11 C -0.3760(4) 0.7153(4) -0.5520(6) 0.0320(14) Uani C12 C -0.2770(4) 0.8831(4) -0.5365(6) 0.0300(14) Uani C13 C -0.2230(4) 0.6901(4) -0.4488(6) 0.0287(12) Uani C14 C -0.2081(3) 0.8132(4) -0.4712(7) 0.0320(14) Uani C15 C -0.3072(5) 0.6410(4) -0.4877(6) 0.0330(16) Uani S2 S -0.0141(1) 1.0035(1) -0.23942(9) 0.0162(3) Uani N6 N -0.1481(3) 1.1311(5) -0.3796(5) 0.0210(12) Uani N7 N -0.1563(3) 1.1177(5) -0.1059(5) 0.0200(12) Uani C10 C -0.1144(4) 1.0899(6) -0.2418(4) 0.0157(16) Uani S3 S -0.0650(1) 1.4479(1) -0.23955(9) 0.0177(3) Uani N4 N 0.0445(3) 1.6122(5) -0.3783(5) 0.0220(12) Uani N5 N 0.0481(3) 1.6095(5) -0.1032(5) 0.0210(12) Uani C8 C 0.0131(4) 1.5635(6) -0.2404(4) 0.0167(16) Uani Br1 Br 0.1905(1) 0.83351(4) -0.24363(3) 0.0143(2) Uani H19 H -0.40660 0.88690 -0.62660 0.0500 Uiso H11 H -0.43830 0.68070 -0.58230 0.0313 Uiso H12 H -0.26690 0.97340 -0.55330 0.0285 Uiso H13 H -0.17290 0.63780 -0.40280 0.0313 Uiso H14 H -0.14630 0.8496 -0.44130 0.0292 Uiso H15 H -0.31950 0.55150 -0.47130 0.0303 Uiso H6A H -0.20560 1.18120 -0.37890 0.0500 Uiso H6B H -0.11540 1.11260 -0.48260 0.0500 Uiso H7A H -0.21420 1.16740 -0.10590 0.0500 Uiso H7B H -0.13050 1.08790 0.00030 0.0500 Uiso H4A H 0.08440 1.69250 -0.36890 0.0500 Uiso H4B H 0.02130 1.58920 -0.47390 0.0500 Uiso H5A H 0.08310 1.68860 -0.12930 0.0500 Uiso H5B H 0.04080 1.57230 0.00620 0.0500 Uiso 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 N9 0.025(2) 0.031(2) 0.026(2) 0.003(1) -0.008(2) 0.005(1) C11 0.027(2) 0.032(2) 0.037(3) -0.001(2) -0.001(2) -0.006(2) C12 0.032(2) 0.025(2) 0.033(3) 0.005(2) -0.009(2) 0.000(2) C13 0.030(2) 0.025(2) 0.031(2) 0.005(2) -0.001(2) 0.006(2) C14 0.029(2) 0.027(2) 0.040(3) 0.005(2) -0.011(2) -0.002(2) C15 0.041(3) 0.021(2) 0.037(3) 0.006(2) 0.003(3) 0.000(2) S2 0.0170(6) 0.0210(6) 0.0105(5) 0.0003(3) 0.0009(5) 0.0052(5) N6 0.025(2) 0.026(2) 0.012(2) 0.000(1) 0.001(2) 0.009(2) N7 0.024(2) 0.024(2) 0.012(2) -0.002(1) 0.001(1) 0.008(1) C10 0.020(3) 0.012(3) 0.015(2) 0.000(1) 0.001(1) 0.000(2) S3 0.0215(6) 0.0220(6) 0.0097(5) -0.0008(3) 0.0010(5) -0.0109(5) N4 0.027(2) 0.028(2) 0.011(2) -0.001(1) -0.001(2) -0.012(1) N5 0.026(2) 0.027(2) 0.010(2) 0.002(1) 0.000(1) -0.012(2) C8 0.021(3) 0.019(3) 0.010(2) 0.000(1) 0.000(1) -0.001(2) Br1 0.0135(3) 0.0134(3) 0.0161(3) 0.0002(1) -0.0005(3) 0.0002(2) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C11 N9 C12 122.2(4) yes C12 N9 H19 119.00 no C11 N9 H19 119.00 no C10 N6 H6B 120.00 no H6A N6 H6B 121.00 no C10 N6 H6A 119.00 no C10 N7 H7B 120.00 no H7A N7 H7B 119.00 no C10 N7 H7A 121.00 no C8 N4 H4B 121.00 no C8 N4 H4A 117.00 no H4A N4 H4B 120.00 no H5A N5 H5B 126.00 no C8 N5 H5B 125.00 no C8 N5 H5A 109.00 no N9 C11 C15 118.9(5) yes N9 C12 C14 120.5(4) yes C14 C13 C15 119.5(5) no C12 C14 C13 119.3(4) no C11 C15 C13 119.5(4) no N9 C11 H11 120.00 no C15 C11 H11 121.00 no C14 C12 H12 120.00 no N9 C12 H12 120.00 no C15 C13 H13 120.00 no C14 C13 H13 120.00 no C12 C14 H14 121.00 no C13 C14 H14 120.00 no C11 C15 H15 120.00 no C13 C15 H15 121.00 no S2 C10 N7 120.1(4) yes N6 C10 N7 119.5(5) yes S2 C10 N6 120.4(4) yes N4 C8 N5 116.4(5) yes S3 C8 N4 121.7(4) yes S3 C8 N5 121.8(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S2 C10 1.731(6) yes S3 C8 1.698(6) yes N9 C11 1.345(6) yes N9 C12 1.323(7) yes N9 H19 1.0100 no N6 C10 1.322(6) yes N7 C10 1.315(6) yes N6 H6B 1.0000 no N6 H6A 1.0000 no N7 H7B 1.0100 no N7 H7A 1.0000 no N4 C8 1.341(6) yes N5 C8 1.343(6) yes N4 H4B 0.9000 no N4 H4A 1.0600 no N5 H5B 1.0000 no N5 H5A 1.0300 no C11 C15 1.391(8) no C12 C14 1.368(7) no C13 C14 1.382(6) no C13 C15 1.368(9) no C11 H11 1.0100 no C12 H12 1.0100 no C13 H13 1.0000 no C14 H14 1.0100 no C15 H15 1.0100 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 N4 H4A Br1 1.0600 2.4100 3.405(5) 156.00 1_565 yes N4 H4B S2 0.9000 2.4800 3.361(5) 168.00 4_574 yes N5 H5A Br1 1.0300 2.4200 3.411(5) 163.00 1_565 yes N5 H5B S2 1.0000 2.4000 3.383(5) 167.00 4_575 yes N6 H6A Br1 1.0000 2.4700 3.378(5) 152.00 3_454 yes N6 H6B S3 1.0000 2.3500 3.331(5) 169.00 4_574 yes N7 H7A Br1 1.0000 2.6000 3.473(5) 146.00 3_454 yes N7 H7B S3 1.0100 2.3900 3.388(5) 171.00 4_575 yes N9 H19 S2 1.0100 2.2600 3.261(5) 175.00 2_474 yes C11 H11 S3 1.0100 2.7400 3.693(6) 157.00 2_474 yes C12 H12 Br1 1.0100 2.7800 3.638(5) 143.00 2_474 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_publ_flag C12 N9 C11 C15 -2.1(7) no C11 N9 C12 C14 1.3(8) no N9 C11 C15 C13 0.8(8) no N9 C12 C14 C13 0.8(8) no C15 C13 C14 C12 -2.0(8) no C14 C13 C15 C11 1.2(8) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139089109