#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:16:13 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245913.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_7245913
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_moiety         'C8 H6 N4 O S'
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2021-10-08 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.776(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8771(5)
_cell_length_b                   5.1276(2)
_cell_length_c                   17.5128(11)
_cell_measurement_reflns_used    2118
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.0280
_cell_measurement_theta_min      4.5710
_cell_volume                     868.28(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -22.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      -45.5339  -57.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00   17.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      -45.5339   57.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega   69.00   95.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -       45.5339   38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   96.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -95.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   91.00  176.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025   45.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00  108.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -95.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   74.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   66.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00  137.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -15.0000  120.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0139419000
_diffrn_orient_matrix_UB_12      -0.0145989000
_diffrn_orient_matrix_UB_13      -0.0891138000
_diffrn_orient_matrix_UB_21      -0.1580294000
_diffrn_orient_matrix_UB_22      -0.0246594000
_diffrn_orient_matrix_UB_23      -0.0101576000
_diffrn_orient_matrix_UB_31      -0.0135745000
_diffrn_orient_matrix_UB_32      0.2993223000
_diffrn_orient_matrix_UB_33      -0.0052047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3500
_diffrn_reflns_point_group_measured_fraction_full 0.736
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.566
_diffrn_reflns_theta_min         4.573
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0530
_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)+(0.1058P)²+0.5486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.295
_reflns_Friedel_fraction_full    0.407
_reflns_Friedel_fraction_max     0.355
_reflns_number_gt                2345
_reflns_number_total             2518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01171a2.cif
_cod_data_source_block           iran-ft-9-cold
_cod_depositor_comments
'Adding full bibliography for 7245912--7245914.cif.'
_cod_original_cell_volume        868.29(8)
_cod_database_code               7245913
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C8 H5 N3 O1 S1'
_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.
;
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7A), N7(H7), C15(H15), C10(H10), C3(H3A), C2(H2), C9(H9),
 C16(H16), C8(H8), C11(H11), C1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
_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
S2 S -0.61302(15) -0.3774(3) -0.46517(8) 0.0238(4) Uani 1 1 d . . . . .
S1 S -0.63751(14) 1.3147(3) -0.01682(8) 0.0251(4) Uani 1 1 d . . . . .
O1 O -0.6224(4) 0.9482(10) -0.1268(3) 0.0294(10) Uani 1 1 d . . . . .
N3 N -0.8385(5) 1.1165(11) -0.1347(3) 0.0210(10) Uani 1 1 d . . . . .
H3 H -0.9253 1.1091 -0.1596 0.025 Uiso 1 1 calc R . . . .
N6 N -0.4203(5) 0.3492(11) -0.2489(3) 0.0229(11) Uani 1 1 d . . . . .
N2 N -0.9370(5) 0.7751(11) -0.2552(3) 0.0199(10) Uani 1 1 d . . . . .
C4 C -0.8028(6) 0.7640(13) -0.2203(3) 0.0214(12) Uani 1 1 d . . . . .
C12 C -0.3576(6) 0.1515(13) -0.2790(3) 0.0220(12) Uani 1 1 d . . . . .
N8 N -0.8004(5) -0.0787(11) -0.4273(3) 0.0241(11) Uani 1 1 d . . . . .
N1 N -0.7586(5) 0.3911(10) -0.2941(3) 0.0217(11) Uani 1 1 d . . . . .
N5 N -0.1358(5) 0.2543(11) -0.2025(3) 0.0235(11) Uani 1 1 d . . . . .
C7 C -0.8338(6) 1.6023(15) 0.0070(4) 0.0283(13) Uani 1 1 d . . . . .
H7A H -0.8848 1.7276 0.0295 0.034 Uiso 1 1 calc R . . . .
C6 C -0.8023(5) 1.2958(13) -0.0745(3) 0.0191(11) Uani 1 1 d . . . . .
N7 N -0.5786(5) 0.0168(10) -0.3561(3) 0.0204(10) Uani 1 1 d . . . . .
H7 H -0.6132 0.1397 -0.3306 0.025 Uiso 1 1 calc R . . . .
C15 C -0.7821(7) -0.4176(14) -0.5124(4) 0.0291(15) Uani 1 1 d . . . . .
H15 H -0.8132 -0.5414 -0.5525 0.035 Uiso 1 1 calc R . . . .
C10 C -0.1971(6) 0.4546(14) -0.1741(4) 0.0264(13) Uani 1 1 d . . . . .
H10 H -0.1425 0.5695 -0.1378 0.032 Uiso 1 1 calc R . . . .
C3 C -0.9796(6) 0.5942(13) -0.3094(3) 0.0212(12) Uani 1 1 d . . . . .
H3A H -1.0736 0.5962 -0.3360 0.025 Uiso 1 1 calc R . . . .
C14 C -0.6691(6) -0.1278(12) -0.4127(3) 0.0218(12) Uani 1 1 d . . . . .
C2 C -0.8926(6) 0.4021(12) -0.3287(3) 0.0219(12) Uani 1 1 d . . . . .
H2 H -0.9291 0.2763 -0.3673 0.026 Uiso 1 1 calc R . . . .
C5 C -0.7458(6) 0.9520(14) -0.1568(4) 0.0258(13) Uani 1 1 d . . . . .
C9 C -0.2169(6) 0.1072(14) -0.2552(3) 0.0241(13) Uani 1 1 d . . . . .
H9 H -0.1767 -0.0346 -0.2776 0.029 Uiso 1 1 calc R . . . .
C16 C -0.8639(6) -0.2488(14) -0.4845(4) 0.0273(14) Uani 1 1 d . . . . .
H16 H -0.9612 -0.2467 -0.5033 0.033 Uiso 1 1 calc R . . . .
N4 N -0.8932(5) 1.4539(12) -0.0566(3) 0.0248(11) Uani 1 1 d . . . . .
C13 C -0.4407(6) -0.0247(13) -0.3390(3) 0.0208(12) Uani 1 1 d . . . . .
C8 C -0.6980(7) 1.5572(13) 0.0351(4) 0.0260(13) Uani 1 1 d . . . . .
H8 H -0.6432 1.6475 0.0778 0.031 Uiso 1 1 calc R . . . .
C11 C -0.3385(6) 0.4990(14) -0.1963(4) 0.0261(13) Uani 1 1 d . . . . .
H11 H -0.3783 0.6402 -0.1735 0.031 Uiso 1 1 calc R . . . .
C1 C -0.7153(6) 0.5721(12) -0.2396(3) 0.0219(13) Uani 1 1 d . . . . .
H1 H -0.6213 0.5700 -0.2130 0.026 Uiso 1 1 calc R . . . .
O2 O -0.3828(4) -0.1952(10) -0.3698(2) 0.0266(9) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C15 S2 C14 87.7(3) . . ?
C8 S1 C6 87.9(3) . . ?
C5 N3 C6 122.9(5) . . ?
C11 N6 C12 116.1(5) . . ?
C3 N2 C4 115.8(5) . . ?
N2 C4 C5 120.0(5) . . ?
N2 C4 C1 121.4(6) . . ?
C1 C4 C5 118.5(5) . . ?
N6 C12 C9 121.1(6) . . ?
N6 C12 C13 119.9(5) . . ?
C9 C12 C13 119.0(6) . . ?
C14 N8 C16 108.0(5) . . ?
C1 N1 C2 115.9(5) . . ?
C9 N5 C10 116.1(5) . . ?
C8 C7 N4 115.3(6) . . ?
N3 C6 S1 123.0(4) . . ?
N4 C6 S1 116.0(4) . . ?
N4 C6 N3 121.0(5) . . ?
C13 N7 C14 122.8(5) . . ?
C16 C15 S2 110.2(5) . . ?
N5 C10 C11 121.8(6) . . ?
N2 C3 C2 123.0(5) . . ?
N8 C14 S2 117.1(5) . . ?
N8 C14 N7 120.3(5) . . ?
N7 C14 S2 122.6(4) . . ?
N1 C2 C3 121.4(6) . . ?
O1 C5 N3 123.8(6) . . ?
O1 C5 C4 120.0(6) . . ?
N3 C5 C4 116.1(5) . . ?
N5 C9 C12 122.8(6) . . ?
C15 C16 N8 117.0(6) . . ?
C6 N4 C7 109.9(5) . . ?
N7 C13 C12 116.4(5) . . ?
O2 C13 C12 120.0(5) . . ?
O2 C13 N7 123.6(5) . . ?
C7 C8 S1 110.9(5) . . ?
N6 C11 C10 122.0(6) . . ?
N1 C1 C4 122.6(6) . . ?
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
S2 C15 1.718(7) . ?
S2 C14 1.731(6) . ?
S1 C6 1.735(5) . ?
S1 C8 1.717(6) . ?
O1 C5 1.225(7) . ?
N3 C6 1.390(8) . ?
N3 C5 1.358(8) . ?
N6 C12 1.350(8) . ?
N6 C11 1.336(8) . ?
N2 C4 1.342(7) . ?
N2 C3 1.332(8) . ?
C4 C5 1.492(9) . ?
C4 C1 1.396(8) . ?
C12 C9 1.387(8) . ?
C12 C13 1.496(9) . ?
N8 C14 1.294(7) . ?
N8 C16 1.379(8) . ?
N1 C2 1.340(7) . ?
N1 C1 1.337(8) . ?
N5 C10 1.339(8) . ?
N5 C9 1.327(8) . ?
C7 N4 1.377(9) . ?
C7 C8 1.351(9) . ?
C6 N4 1.294(8) . ?
N7 C14 1.404(8) . ?
N7 C13 1.350(7) . ?
C15 C16 1.343(9) . ?
C10 C11 1.390(8) . ?
C3 C2 1.393(8) . ?
C13 O2 1.229(8) . ?
