#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:16:13 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245914.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_7245914
loop_
_publ_author_name
'Tavakoli-Quchani, Fatemeh'
'Salimi, Alireza'
'Notash, Behrouz'
'Samie, Ali'
'Garrison, Jered C.'
_publ_section_title
;
 Polymorphism in carboxamide compounds with high-Z′ crystal
 structures
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              299
_journal_page_last               308
_journal_paper_doi               10.1039/D2CE01171A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.58(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.421(4)
_cell_length_b                   11.050(2)
_cell_length_c                   8.1836(16)
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.247
_cell_measurement_theta_min      2.825
_cell_volume                     1720.5(6)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2426
_diffrn_reflns_av_unetI/netI     0.2499
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8882
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.825
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.343
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.2322
_refine_ls_R_factor_gt           0.1225
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0544P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1448
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01171a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7245912--7245914.cif.'
_cod_original_cell_volume        1720.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245914
_shelx_shelxl_version_number     2018/3
_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.
;
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
C1 C 0.1586(5) 0.2569(9) 1.1457(13) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.2305(4) 0.1361(9) 1.3116(12) 0.0186(16) Uani 1 1 d . . . . .
H2 H 0.248369 0.062714 1.357097 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2598(5) 0.2459(8) 1.3679(13) 0.0186(16) Uani 1 1 d . . . . .
H3 H 0.299111 0.255117 1.453077 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0868(4) 0.3995(8) 0.9683(12) 0.0182(14) Uani 1 1 d . . . . .
C5 C 0.0242(5) 0.4172(8) 0.8283(12) 0.0177(12) Uani 1 1 d . . . . .
C6 C -0.0722(5) 0.3422(8) 0.6516(13) 0.025(3) Uani 1 1 d . . . . .
H6 H -0.101270 0.277898 0.609308 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0869(5) 0.4564(8) 0.5822(12) 0.015(2) Uani 1 1 d . . . . .
H7 H -0.126064 0.467522 0.497325 0.019 Uiso 1 1 calc R U . . .
C8 C 0.0094(4) 0.5294(8) 0.7581(12) 0.0177(12) Uani 1 1 d . . . . .
H8 H 0.039213 0.593446 0.797859 0.021 Uiso 1 1 calc R U . . .
N1 N 0.1741(4) 0.1432(7) 1.1856(10) 0.0178(18) Uani 1 1 d . . . . .
N2 N 0.1023(4) 0.2853(7) 1.0211(10) 0.0182(14) Uani 1 1 d . . . . .
H2N H 0.075676 0.227550 0.974705 0.022 Uiso 1 1 calc R U . . .
N3 N -0.0168(4) 0.3210(7) 0.7788(10) 0.0177(12) Uani 1 1 d . . . . .
N4 N -0.0451(4) 0.5505(7) 0.6366(10) 0.022(2) Uani 1 1 d . . . . .
O1 O 0.1205(3) 0.4890(6) 1.0314(9) 0.0221(16) Uani 1 1 d . . . . .
S1 S 0.21365(12) 0.3634(2) 1.2592(3) 0.0201(6) Uani 1 1 d . . . . .
C9 C 0.3391(5) 0.7742(8) 0.9877(13) 0.0160(14) Uani 1 1 d . . . . .
C10 C 0.2645(4) 0.6602(9) 1.0835(12) 0.0204(16) Uani 1 1 d . . . . .
H10 H 0.245105 0.587752 1.110486 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2369(5) 0.7687(8) 1.1126(12) 0.0204(16) Uani 1 1 d . . . . .
H11 H 0.197645 0.779485 1.160056 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4120(5) 0.9179(8) 0.8759(13) 0.021(2) Uani 1 1 d . . . . .
C13 C 0.4743(5) 0.9316(7) 0.7983(12) 0.015(2) Uani 1 1 d . . . . .
C14 C 0.5675(5) 0.8546(9) 0.7066(13) 0.0266(16) Uani 1 1 d . . . . .
H14 H 0.596119 0.789647 0.691988 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5848(5) 0.9676(8) 0.6560(12) 0.019(2) Uani 1 1 d . . . . .
H15 H 0.623795 0.976045 0.606981 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4912(5) 1.0437(8) 0.7456(12) 0.019(2) Uani 1 1 d . . . . .
H16 H 0.462457 1.108763 0.759148 0.022 Uiso 1 1 calc R U . . .
N5 N 0.3229(4) 0.6627(7) 1.0119(11) 0.023(2) Uani 1 1 d . . . . .
N6 N 0.3957(4) 0.8037(7) 0.9157(10) 0.0160(14) Uani 1 1 d . . . . .
H6N H 0.422202 0.745825 0.894811 0.019 Uiso 1 1 calc R U . . .
N7 N 0.5115(4) 0.8333(7) 0.7759(11) 0.0266(16) Uani 1 1 d . . . . .
N8 N 0.5470(4) 1.0646(6) 0.6756(11) 0.022(2) Uani 1 1 d . . . . .
O2 O 0.3791(3) 1.0053(5) 0.9069(9) 0.0216(16) Uani 1 1 d . . . . .
S2 S 0.28549(12) 0.8841(2) 1.0485(3) 0.0220(6) Uani 1 1 d . . . . .
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
_geom_angle_publ_flag
N1 C1 N2 120.7(9) . . ?
N1 C1 S1 115.5(7) . . ?
N2 C1 S1 123.9(7) . . ?
N1 C2 C3 115.0(8) . . ?
C2 C3 S1 110.7(7) . . ?
O1 C4 N2 123.2(8) . . ?
O1 C4 C5 119.4(8) . . ?
N2 C4 C5 117.3(8) . . ?
N3 C5 C8 121.9(8) . . ?
N3 C5 C4 117.8(8) . . ?
C8 C5 C4 120.3(8) . . ?
N3 C6 C7 122.4(8) . . ?
N4 C7 C6 120.6(8) . . ?
N4 C8 C5 122.9(9) . . ?
C1 N1 C2 110.8(8) . . ?
C4 N2 C1 123.0(8) . . ?
C5 N3 C6 115.1(8) . . ?
C8 N4 C7 117.0(8) . . ?
C3 S1 C1 88.0(5) . . ?
N5 C9 N6 121.8(8) . . ?
N5 C9 S2 116.3(7) . . ?
N6 C9 S2 121.9(7) . . ?
C11 C10 N5 116.5(9) . . ?
C10 C11 S2 109.9(8) . . ?
O2 C12 N6 122.2(9) . . ?
O2 C12 C13 121.1(8) . . ?
N6 C12 C13 116.6(8) . . ?
N7 C13 C16 121.4(9) . . ?
N7 C13 C12 119.0(8) . . ?
C16 C13 C12 119.6(8) . . ?
N7 C14 C15 123.5(9) . . ?
N8 C15 C14 121.4(10) . . ?
N8 C16 C13 123.6(9) . . ?
C9 N5 C10 109.3(8) . . ?
C12 N6 C9 124.4(8) . . ?
C13 N7 C14 114.8(8) . . ?
C15 N8 C16 115.2(8) . . ?
C11 S2 C9 88.0(5) . . ?
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
C1 N1 1.318(12) . ?
C1 N2 1.373(12) . ?
C1 S1 1.730(10) . ?
C2 N1 1.347(11) . ?
C2 C3 1.379(13) . ?
C3 S1 1.721(9) . ?
C4 O1 1.239(10) . ?
C4 N2 1.349(12) . ?
C4 C5 1.507(12) . ?
C5 N3 1.342(11) . ?
C5 C8 1.372(13) . ?
C6 N3 1.358(12) . ?
C6 C7 1.390(12) . ?
C7 N4 1.339(12) . ?
C8 N4 1.320(11) . ?
C9 N5 1.297(11) . ?
C9 N6 1.386(12) . ?
C9 S2 1.737(9) . ?
C10 C11 1.354(14) . ?
C10 N5 1.376(13) . ?
C11 S2 1.730(10) . ?
C12 O2 1.212(10) . ?
C12 N6 1.355(12) . ?
C12 C13 1.484(14) . ?
C13 N7 1.337(11) . ?
C13 C16 1.373(12) . ?
C14 N7 1.345(13) . ?
C14 C15 1.378(14) . ?
C15 N8 1.327(12) . ?
C16 N8 1.344(13) . ?
