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#$Date: 2023-07-11 10:17:09 +0300 (Tue, 11 Jul 2023) $
#$Revision: 285142 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107459.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_8107459
loop_
_publ_author_name
'Tang, Huawei'
'Han, Qianqian'
'Liu, Lijuan'
_publ_section_title
;
 Crystal structure of
 tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate --
 1,2,4-thiadiazole-3,5-diamine -- water (1/1/1), C17H37N9O3S2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              425
_journal_page_last               427
_journal_paper_doi               10.1515/ncrs-2022-0566
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C12 H28 N, C3 H3 N4 O2 S, C2 H4 N4 S, H2 O'
_chemical_formula_sum            'C17 H37 N9 O3 S2'
_chemical_formula_weight         479.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.493(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8492(13)
_cell_length_b                   17.285(3)
_cell_length_c                   16.810(3)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.36
_cell_volume                     2566.5(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12815
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.691
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4511
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0704P)²+0.3342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3774
_reflns_number_total             4511
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0566_suppl.cif
_cod_data_source_block           2
_cod_original_cell_volume        2566.4(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107459
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12243(6) 0.17443(3) 0.59153(3) 0.04788(17) Uani 1 1 d . . . . .
C1 C 0.1383(2) 0.10176(10) 0.46849(11) 0.0414(4) Uani 1 1 d . . . . .
N1 N 0.07948(19) 0.09445(9) 0.53823(10) 0.0506(4) Uani 1 1 d . . . . .
O1 O 0.37108(19) 0.39474(8) 0.57551(9) 0.0631(4) Uani 1 1 d . . . . .
O1W O 0.2481(2) 0.04833(11) 0.24913(10) 0.0709(5) Uani 1 1 d D . . . .
H1WA H 0.312(3) 0.0115(13) 0.2426(16) 0.106 Uiso 1 1 d D U . . .
H1WB H 0.244(3) 0.0757(15) 0.2056(11) 0.106 Uiso 1 1 d D U . . .
S2 S 0.43503(6) 0.13059(3) 0.73061(3) 0.05315(18) Uani 1 1 d . . . . .
C2 C 0.21949(19) 0.21342(10) 0.51537(10) 0.0386(4) Uani 1 1 d . . . . .
N2 N 0.1206(2) 0.04674(10) 0.41115(11) 0.0592(5) Uani 1 1 d . . . . .
H2A H 0.0697 0.0055 0.4198 0.071 Uiso 1 1 calc R U . . .
H2B H 0.1603 0.0531 0.3662 0.071 Uiso 1 1 calc R U . . .
O2 O 0.21952(19) 0.31527(9) 0.64117(8) 0.0597(4) Uani 1 1 d . . . . .
C3 C 0.2935(2) 0.33514(11) 0.58270(11) 0.0465(5) Uani 1 1 d . . . . .
N3 N 0.21863(17) 0.16771(8) 0.45213(9) 0.0419(4) Uani 1 1 d . . . . .
C4 C 0.3784(2) 0.19067(10) 0.80634(11) 0.0431(4) Uani 1 1 d . . . . .
N4 N 0.28868(19) 0.28350(9) 0.51791(9) 0.0484(4) Uani 1 1 d . . . . .
H4A H 0.3335 0.2976 0.4763 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5103(2) 0.09813(10) 0.86760(11) 0.0428(4) Uani 1 1 d . . . . .
N5 N 0.2969(2) 0.25515(10) 0.79488(10) 0.0575(5) Uani 1 1 d . . . . .
H5A H 0.2740 0.2827 0.8350 0.069 Uiso 1 1 calc R U . . .
H5B H 0.2674 0.2692 0.7474 0.069 Uiso 1 1 calc R U . . .
N6 N 0.42830(18) 0.16483(9) 0.87695(9) 0.0432(4) Uani 1 1 d . . . . .
C6 C 0.3234(2) 0.80349(13) 0.82371(13) 0.0562(5) Uani 1 1 d . . . . .
H6A H 0.3909 0.7693 0.7969 0.067 Uiso 1 1 calc R U . . .
H6B H 0.3858 0.8387 0.8564 0.067 Uiso 1 1 calc R U . . .
N7 N 0.5300(2) 0.07139(9) 0.79536(10) 0.0506(4) Uani 1 1 d . . . . .
C7 C 0.2309(3) 0.75532(19) 0.87778(17) 0.0858(8) Uani 1 1 d . . . . .
H7A H 0.1589 0.7885 0.9026 0.103 Uiso 1 1 calc R U . . .
H7B H 0.1740 0.7171 0.8461 0.103 Uiso 1 1 calc R U . . .
N8 N 0.5714(2) 0.06313(10) 0.93440(10) 0.0580(5) Uani 1 1 d . . . . .
H8D H 0.6251 0.0220 0.9306 0.070 Uiso 1 1 calc R U . . .
H8E H 0.5563 0.0821 0.9805 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3265(4) 0.7150(2) 0.94119(18) 0.1016(10) Uani 1 1 d . . . . .
H8A H 0.2629 0.6853 0.9739 0.152 Uiso 1 1 calc R U . . .
H8B H 0.3965 0.6813 0.9170 0.152 Uiso 1 1 calc R U . . .
H8C H 0.3814 0.7526 0.9735 0.152 Uiso 1 1 calc R U . . .
N9 N 0.23328(16) 0.85037(10) 0.76111(10) 0.0474(4) Uani 1 1 d . . . . .
C9 C 0.1309(2) 0.90868(13) 0.79916(14) 0.0577(5) Uani 1 1 d . . . . .
H9A H 0.0803 0.9392 0.7571 0.069 Uiso 1 1 calc R U . . .
H9B H 0.0535 0.8805 0.8256 0.069 Uiso 1 1 calc R U . . .
C10 C 0.2082(3) 0.96331(18) 0.85885(19) 0.0910(9) Uani 1 1 d . . . . .
H10A H 0.2704 0.9335 0.8972 0.109 Uiso 1 1 calc R U . . .
H10B H 0.2746 0.9974 0.8312 0.109 Uiso 1 1 calc R U . . .
C11 C 0.1029(5) 1.0096(3) 0.9010(3) 0.1485(18) Uani 1 1 d . . . . .
H11A H 0.1580 1.0431 0.9379 0.223 Uiso 1 1 calc R U . . .
H11B H 0.0424 1.0402 0.8635 0.223 Uiso 1 1 calc R U . . .
H11C H 0.0383 0.9763 0.9295 0.223 Uiso 1 1 calc R U . . .
C12 C 0.3501(2) 0.89099(13) 0.71169(13) 0.0519(5) Uani 1 1 d . . . . .
H12A H 0.4115 0.9243 0.7470 0.062 Uiso 1 1 calc R U . . .
H12B H 0.4166 0.8518 0.6917 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2889(3) 0.93893(15) 0.64195(14) 0.0649(6) Uani 1 1 d . . . . .
H13A H 0.2363 0.9838 0.6612 0.078 Uiso 1 1 calc R U . . .
H13B H 0.2173 0.9086 0.6090 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4181(3) 0.96494(17) 0.59285(15) 0.0755(7) Uani 1 1 d . . . . .
H14A H 0.3786 0.9954 0.5486 0.113 Uiso 1 1 calc R U . . .
H14B H 0.4881 0.9955 0.6255 0.113 Uiso 1 1 calc R U . . .
H14C H 0.4692 0.9204 0.5735 0.113 Uiso 1 1 calc R U . . .
C15 C 0.1293(2) 0.79903(12) 0.70784(14) 0.0537(5) Uani 1 1 d . . . . .
H15A H 0.0557 0.7753 0.7407 0.064 Uiso 1 1 calc R U . . .
H15B H 0.0741 0.8318 0.6693 0.064 Uiso 1 1 calc R U . . .
C16 C 0.2058(3) 0.73593(14) 0.66329(15) 0.0660(6) Uani 1 1 d . . . . .
H16A H 0.2512 0.6989 0.7010 0.079 Uiso 1 1 calc R U . . .
H16B H 0.2859 0.7581 0.6336 0.079 Uiso 1 1 calc R U . . .
C17 C 0.0938(4) 0.6951(2) 0.6067(2) 0.1111(13) Uani 1 1 d . . . . .
H17A H 0.1446 0.6552 0.5789 0.167 Uiso 1 1 calc R U . . .
H17B H 0.0153 0.6725 0.6361 0.167 Uiso 1 1 calc R U . . .
H17C H 0.0500 0.7316 0.5689 0.167 Uiso 1 1 calc R U . . .
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'
S S 0.1246 0.1234 '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_3
N1 S1 C2 91.86(8) . .
N1 C1 N2 122.03(17) . .
N1 C1 N3 119.53(17) . .
N2 C1 N3 118.43(16) . .
C1 N1 S1 107.89(13) . .
H1WA O1W H1WB 106.8(19) . .
N7 S2 C4 92.55(9) . .
N3 C2 N4 122.58(16) . .
N3 C2 S1 112.62(13) . .
N4 C2 S1 124.80(14) . .
C1 N2 H2A 120.0 . .
C1 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
O1 C3 O2 127.95(18) . .
O1 C3 N4 116.09(18) . .
O2 C3 N4 115.96(17) . .
C2 N3 C1 108.10(15) . .
N6 C4 N5 124.12(17) . .
N6 C4 S2 111.13(13) . .
N5 C4 S2 124.74(15) . .
C2 N4 C3 125.67(16) . .
C2 N4 H4A 117.2 . .
C3 N4 H4A 117.2 . .
N7 C5 N8 122.43(17) . .
N7 C5 N6 119.87(16) . .
N8 C5 N6 117.68(17) . .
C4 N5 H5A 120.0 . .
C4 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
C4 N6 C5 109.33(15) . .
C7 C6 N9 115.52(18) . .
C7 C6 H6A 108.4 . .
N9 C6 H6A 108.4 . .
C7 C6 H6B 108.4 . .
N9 C6 H6B 108.4 . .
H6A C6 H6B 107.5 . .
C5 N7 S2 107.07(13) . .
C8 C7 C6 112.5(2) . .
C8 C7 H7A 109.1 . .
C6 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C5 N8 H8D 120.0 . .
C5 N8 H8E 120.0 . .
H8D N8 H8E 120.0 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 N9 C9 111.32(16) . .
C6 N9 C15 111.65(16) . .
C9 N9 C15 106.16(14) . .
C6 N9 C12 106.08(14) . .
C9 N9 C12 111.24(16) . .
C15 N9 C12 110.48(16) . .
C10 C9 N9 115.85(18) . .
C10 C9 H9A 108.3 . .
N9 C9 H9A 108.3 . .
C10 C9 H9B 108.3 . .
N9 C9 H9B 108.3 . .
H9A C9 H9B 107.4 . .
C11 C10 C9 113.1(3) . .
C11 C10 H10A 109.0 . .
C9 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 N9 116.74(16) . .
C13 C12 H12A 108.1 . .
N9 C12 H12A 108.1 . .
C13 C12 H12B 108.1 . .
N9 C12 H12B 108.1 . .
H12A C12 H12B 107.3 . .
C12 C13 C14 109.79(19) . .
C12 C13 H13A 109.7 . .
C14 C13 H13A 109.7 . .
C12 C13 H13B 109.7 . .
C14 C13 H13B 109.7 . .
H13A C13 H13B 108.2 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 N9 116.02(16) . .
C16 C15 H15A 108.3 . .
N9 C15 H15A 108.3 . .
C16 C15 H15B 108.3 . .
N9 C15 H15B 108.3 . .
H15A C15 H15B 107.4 . .
C15 C16 C17 110.7(2) . .
C15 C16 H16A 109.5 . .
C17 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C17 C16 H16B 109.5 . .
H16A C16 H16B 108.1 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N1 1.6785(17) .
S1 C2 1.7219(18) .
C1 N1 1.317(2) .
C1 N2 1.356(2) .
C1 N3 1.380(2) .
O1 C3 1.248(2) .
O1W H1WA 0.863(10) .
O1W H1WB 0.870(10) .
S2 N7 1.6811(17) .
S2 C4 1.7401(19) .
C2 N3 1.324(2) .
C2 N4 1.357(2) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
O2 C3 1.261(2) .
C3 N4 1.407(2) .
C4 N6 1.319(2) .
C4 N5 1.335(2) .
N4 H4A 0.8600 .
C5 N7 1.321(2) .
C5 N8 1.358(2) .
C5 N6 1.376(2) .
N5 H5A 0.8600 .
N5 H5B 0.8600 .
C6 C7 1.510(3) .
C6 N9 1.516(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.492(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
N8 H8D 0.8600 .
N8 H8E 0.8600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
N9 C9 1.522(3) .
N9 C15 1.528(2) .
N9 C12 1.535(2) .
C9 C10 1.511(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.446(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.509(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.518(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.507(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.507(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
