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#$Date: 2023-04-06 10:44:04 +0300 (Thu, 06 Apr 2023) $
#$Revision: 282464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107054.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_8107054
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Ajarim, Mansour D.'
'Alobaid, Abdulrahman M.'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of
 2-(3-(benzofuran-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazole,
 C26H19N3OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              935
_journal_page_last               936
_journal_paper_doi               10.1515/ncrs-2016-0012
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C26 H19 N3 O S'
_chemical_formula_weight         421.50
_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
_cell_angle_alpha                90
_cell_angle_beta                 106.217(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0921(19)
_cell_length_b                   5.6740(8)
_cell_length_c                   14.417(2)
_cell_measurement_reflns_used    1447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.81
_cell_measurement_theta_min      2.94
_cell_volume                     1028.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1607
_diffrn_reflns_av_unetI/netI     0.1459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16855
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.474
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0564
_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)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2383
_reflns_number_total             3610
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0012_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8107054
_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'
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
S1A S 0.06899(11) -0.0930(2) -1.01724(10) 0.0156(4) Uani 1 1 d . . . . .
O1A O -0.0819(3) 0.1101(6) -1.3660(3) 0.0161(10) Uani 1 1 d . . . . .
N1A N 0.2199(4) 0.2094(8) -0.9448(3) 0.0136(11) Uani 1 1 d . . . . .
N2A N 0.1457(4) 0.2438(7) -1.1117(3) 0.0147(12) Uani 1 1 d . . . . .
N3A N 0.0661(3) 0.1710(8) -1.1924(3) 0.0138(11) Uani 1 1 d . . . . .
C1A C 0.2853(4) -0.0509(10) -0.6967(4) 0.0181(14) Uani 1 1 d . . . . .
H1 H 0.2433 -0.1857 -0.7082 0.022 Uiso 1 1 calc R U . . .
C2A C 0.3543(4) -0.0137(10) -0.6064(4) 0.0213(16) Uani 1 1 d . . . . .
H2 H 0.3569 -0.1221 -0.5574 0.026 Uiso 1 1 calc R U . . .
C3A C 0.4194(4) 0.1819(10) -0.5875(4) 0.0199(15) Uani 1 1 d . . . . .
H3 H 0.4672 0.2038 -0.5270 0.024 Uiso 1 1 calc R U . . .
C4A C 0.4119(4) 0.3456(9) -0.6610(4) 0.0207(15) Uani 1 1 d . . . . .
H4 H 0.4547 0.4793 -0.6493 0.025 Uiso 1 1 calc R U . . .
C5A C 0.3418(5) 0.3107(9) -0.7505(4) 0.0192(15) Uani 1 1 d . . . . .
H5 H 0.3369 0.4230 -0.7986 0.023 Uiso 1 1 calc R U . . .
C6A C 0.2777(4) 0.1098(9) -0.7708(4) 0.0126(14) Uani 1 1 d . . . . .
C7A C 0.2071(4) 0.0678(9) -0.8688(4) 0.0130(14) Uani 1 1 d . . . . .
C8A C 0.1321(4) -0.1022(11) -0.8948(3) 0.0156(13) Uani 1 1 d . . . . .
H6 H 0.1165 -0.2102 -0.8523 0.019 Uiso 1 1 calc R U . . .
C9A C 0.1526(4) 0.1410(9) -1.0248(4) 0.0122(14) Uani 1 1 d . . . . .
C10A C 0.1989(4) 0.4664(8) -1.1261(4) 0.0133(14) Uani 1 1 d . . . . .
H10A H 0.1969 0.5801 -1.0755 0.016 Uiso 1 1 calc R U . . .
C11A C 0.1243(4) 0.5469(8) -1.2241(4) 0.0173(15) Uani 1 1 d . . . . .
H11A H 0.0821 0.6819 -1.2162 0.021 Uiso 1 1 calc R U . . .
H11B H 0.1643 0.5868 -1.2693 0.021 Uiso 1 1 calc R U . . .
C12A C 0.0552(4) 0.3339(8) -1.2576(4) 0.0123(14) Uani 1 1 d . . . . .
C13A C -0.0213(4) 0.3138(8) -1.3497(4) 0.0147(14) Uani 1 1 d . . . . .
C14A C -0.0518(4) 0.4648(9) -1.4251(4) 0.0143(14) Uani 1 1 d . . . . .
H14A H -0.0219 0.6111 -1.4304 0.017 Uiso 1 1 calc R U . . .
C15A C -0.1391(4) 0.3559(9) -1.4954(4) 0.0144(14) Uani 1 1 d . . . . .
C16A C -0.2076(4) 0.4182(11) -1.5846(4) 0.0193(13) Uani 1 1 d . . . . .
H16A H -0.1996 0.5610 -1.6136 0.023 Uiso 1 1 calc R U . . .
C17A C -0.2881(5) 0.2626(10) -1.6295(4) 0.0255(17) Uani 1 1 d . . . . .
H17A H -0.3344 0.3023 -1.6890 0.031 Uiso 1 1 calc R U . . .
C18A C -0.3009(5) 0.0470(9) -1.5868(4) 0.0197(15) Uani 1 1 d . . . . .
H18A H -0.3558 -0.0535 -1.6182 0.024 Uiso 1 1 calc R U . . .
C19A C -0.2330(4) -0.0189(9) -1.4985(4) 0.0188(15) Uani 1 1 d . . . . .
H19A H -0.2398 -0.1629 -1.4699 0.023 Uiso 1 1 calc R U . . .
C20A C -0.1552(4) 0.1398(9) -1.4555(4) 0.0136(14) Uani 1 1 d . . . . .
C21A C 0.3121(4) 0.4237(10) -1.1273(3) 0.0134(12) Uani 1 1 d . . . . .
C22A C 0.3418(4) 0.2237(9) -1.1678(4) 0.0159(14) Uani 1 1 d . . . . .
H22A H 0.2918 0.1064 -1.1919 0.019 Uiso 1 1 calc R U . . .
C23A C 0.4452(4) 0.1959(10) -1.1730(4) 0.0194(15) Uani 1 1 d . . . . .
H23A H 0.4641 0.0601 -1.2003 0.023 Uiso 1 1 calc R U . . .
C24A C 0.5199(5) 0.3684(10) -1.1379(4) 0.0226(15) Uani 1 1 d . . . . .
H24A H 0.5893 0.3501 -1.1416 0.027 Uiso 1 1 calc R U . . .
C25A C 0.4912(5) 0.5681(10) -1.0972(4) 0.0224(16) Uani 1 1 d . . . . .
H25A H 0.5417 0.6842 -1.0728 0.027 Uiso 1 1 calc R U . . .
C26A C 0.3881(4) 0.5985(9) -1.0920(4) 0.0179(14) Uani 1 1 d . . . . .
H26A H 0.3694 0.7352 -1.0651 0.021 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
C8A S1A C9A 87.6(3) . .
C20A O1A C13A 105.8(4) . .
C9A N1A C7A 108.8(5) . .
C9A N2A N3A 118.9(4) . .
C9A N2A C10A 125.4(5) . .
N3A N2A C10A 114.1(4) . .
C12A N3A N2A 107.4(4) . .
C2A C1A C6A 121.0(6) . .
C2A C1A H1 119.5 . .
C6A C1A H1 119.5 . .
C1A C2A C3A 121.0(6) . .
C1A C2A H2 119.5 . .
C3A C2A H2 119.5 . .
C2A C3A C4A 118.6(5) . .
C2A C3A H3 120.7 . .
C4A C3A H3 120.7 . .
C5A C4A C3A 120.4(5) . .
C5A C4A H4 119.8 . .
C3A C4A H4 119.8 . .
C4A C5A C6A 121.2(5) . .
C4A C5A H5 119.4 . .
C6A C5A H5 119.4 . .
C1A C6A C5A 117.8(5) . .
C1A C6A C7A 121.5(5) . .
C5A C6A C7A 120.7(5) . .
C8A C7A N1A 115.3(5) . .
C8A C7A C6A 126.4(5) . .
N1A C7A C6A 118.3(5) . .
C7A C8A S1A 111.4(4) . .
C7A C8A H6 124.3 . .
S1A C8A H6 124.3 . .
N1A C9A N2A 122.9(5) . .
N1A C9A S1A 117.0(4) . .
N2A C9A S1A 120.2(4) . .
N2A C10A C21A 111.5(4) . .
N2A C10A C11A 100.2(4) . .
C21A C10A C11A 114.2(4) . .
N2A C10A H10A 110.2 . .
C21A C10A H10A 110.2 . .
C11A C10A H10A 110.2 . .
C12A C11A C10A 103.0(4) . .
C12A C11A H11A 111.2 . .
C10A C11A H11A 111.2 . .
C12A C11A H11B 111.2 . .
C10A C11A H11B 111.2 . .
H11A C11A H11B 109.1 . .
N3A C12A C13A 121.6(5) . .
N3A C12A C11A 113.9(5) . .
C13A C12A C11A 124.4(5) . .
C14A C13A O1A 111.4(5) . .
C14A C13A C12A 132.0(5) . .
O1A C13A C12A 116.4(5) . .
C13A C14A C15A 107.0(4) . .
C13A C14A H14A 126.5 . .
C15A C14A H14A 126.5 . .
C16A C15A C20A 118.1(5) . .
C16A C15A C14A 136.2(5) . .
C20A C15A C14A 105.6(5) . .
C17A C16A C15A 118.5(5) . .
C17A C16A H16A 120.7 . .
C15A C16A H16A 120.7 . .
C16A C17A C18A 121.3(6) . .
C16A C17A H17A 119.4 . .
C18A C17A H17A 119.4 . .
C19A C18A C17A 121.0(6) . .
C19A C18A H18A 119.5 . .
C17A C18A H18A 119.5 . .
C20A C19A C18A 116.3(5) . .
C20A C19A H19A 121.8 . .
C18A C19A H19A 121.8 . .
C19A C20A O1A 125.1(5) . .
C19A C20A C15A 124.7(5) . .
O1A C20A C15A 110.2(5) . .
C22A C21A C26A 118.7(5) . .
C22A C21A C10A 122.1(5) . .
C26A C21A C10A 119.0(5) . .
C23A C22A C21A 120.8(5) . .
C23A C22A H22A 119.6 . .
C21A C22A H22A 119.6 . .
C24A C23A C22A 120.3(5) . .
C24A C23A H23A 119.9 . .
C22A C23A H23A 119.9 . .
C25A C24A C23A 119.4(6) . .
C25A C24A H24A 120.3 . .
C23A C24A H24A 120.3 . .
C24A C25A C26A 120.9(6) . .
C24A C25A H25A 119.6 . .
C26A C25A H25A 119.6 . .
C25A C26A C21A 120.0(5) . .
C25A C26A H26A 120.0 . .
C21A C26A H26A 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A C8A 1.728(5) .
S1A C9A 1.743(5) .
O1A C20A 1.386(6) .
O1A C13A 1.385(6) .
N1A C9A 1.301(6) .
N1A C7A 1.406(6) .
N2A C9A 1.363(6) .
N2A N3A 1.390(6) .
N2A C10A 1.484(6) .
N3A C12A 1.297(6) .
C1A C2A 1.378(7) .
C1A C6A 1.386(7) .
C1A H1 0.9300 .
C2A C3A 1.379(7) .
C2A H2 0.9300 .
C3A C4A 1.391(7) .
C3A H3 0.9300 .
C4A C5A 1.374(7) .
C4A H4 0.9300 .
C5A C6A 1.397(7) .
C5A H5 0.9300 .
C6A C7A 1.476(7) .
C7A C8A 1.352(7) .
C8A H6 0.9300 .
C10A C21A 1.506(7) .
C10A C11A 1.546(7) .
C10A H10A 0.9800 .
C11A C12A 1.506(6) .
C11A H11A 0.9700 .
C11A H11B 0.9700 .
C12A C13A 1.427(7) .
C13A C14A 1.354(7) .
C14A C15A 1.439(7) .
C14A H14A 0.9300 .
C15A C16A 1.393(7) .
C15A C20A 1.395(7) .
C16A C17A 1.388(7) .
C16A H16A 0.9300 .
C17A C18A 1.401(7) .
C17A H17A 0.9300 .
C18A C19A 1.385(7) .
C18A H18A 0.9300 .
C19A C20A 1.371(7) .
C19A H19A 0.9300 .
C21A C22A 1.381(7) .
C21A C26A 1.396(7) .
C22A C23A 1.385(7) .
C22A H22A 0.9300 .
C23A C24A 1.377(7) .
C23A H23A 0.9300 .
C24A C25A 1.376(7) .
C24A H24A 0.9300 .
C25A C26A 1.383(7) .
C25A H25A 0.9300 .
C26A H26A 0.9300 .
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
C9A N2A N3A C12A 161.6(5) . . . .
C10A N2A N3A C12A -4.8(6) . . . .
C6A C1A C2A C3A -1.4(9) . . . .
C1A C2A C3A C4A 1.9(8) . . . .
C2A C3A C4A C5A -0.7(8) . . . .
C3A C4A C5A C6A -1.1(9) . . . .
C2A C1A C6A C5A -0.4(8) . . . .
C2A C1A C6A C7A 177.7(5) . . . .
C4A C5A C6A C1A 1.6(8) . . . .
C4A C5A C6A C7A -176.5(5) . . . .
C9A N1A C7A C8A 0.8(6) . . . .
C9A N1A C7A C6A 178.4(5) . . . .
C1A C6A C7A C8A 10.9(8) . . . .
C5A C6A C7A C8A -171.1(5) . . . .
C1A C6A C7A N1A -166.4(5) . . . .
C5A C6A C7A N1A 11.6(8) . . . .
N1A C7A C8A S1A -1.5(6) . . . .
C6A C7A C8A S1A -178.8(4) . . . .
C9A S1A C8A C7A 1.2(4) . . . .
C7A N1A C9A N2A -179.8(5) . . . .
C7A N1A C9A S1A 0.2(6) . . . .
N3A N2A C9A N1A -175.3(5) . . . .
C10A N2A C9A N1A -10.5(8) . . . .
N3A N2A C9A S1A 4.7(6) . . . .
C10A N2A C9A S1A 169.5(4) . . . .
C8A S1A C9A N1A -0.9(4) . . . .
C8A S1A C9A N2A 179.1(4) . . . .
C9A N2A C10A C21A 83.7(6) . . . .
N3A N2A C10A C21A -110.9(5) . . . .
C9A N2A C10A C11A -155.1(5) . . . .
N3A N2A C10A C11A 10.3(5) . . . .
N2A C10A C11A C12A -10.9(5) . . . .
C21A C10A C11A C12A 108.4(5) . . . .
N2A N3A C12A C13A -179.6(5) . . . .
N2A N3A C12A C11A -3.6(6) . . . .
C10A C11A C12A N3A 9.8(6) . . . .
C10A C11A C12A C13A -174.3(5) . . . .
C20A O1A C13A C14A -1.3(6) . . . .
C20A O1A C13A C12A 175.2(5) . . . .
N3A C12A C13A C14A 174.7(6) . . . .
C11A C12A C13A C14A -0.9(10) . . . .
N3A C12A C13A O1A -0.9(8) . . . .
C11A C12A C13A O1A -176.5(5) . . . .
O1A C13A C14A C15A 0.8(6) . . . .
C12A C13A C14A C15A -174.9(6) . . . .
C13A C14A C15A C16A 176.9(6) . . . .
C13A C14A C15A C20A 0.0(6) . . . .
C20A C15A C16A C17A -0.2(8) . . . .
C14A C15A C16A C17A -176.8(6) . . . .
C15A C16A C17A C18A -0.1(8) . . . .
C16A C17A C18A C19A -0.4(9) . . . .
C17A C18A C19A C20A 1.2(8) . . . .
C18A C19A C20A O1A 177.8(5) . . . .
C18A C19A C20A C15A -1.6(9) . . . .
C13A O1A C20A C19A -178.2(5) . . . .
C13A O1A C20A C15A 1.3(6) . . . .
C16A C15A C20A C19A 1.1(8) . . . .
C14A C15A C20A C19A 178.6(5) . . . .
C16A C15A C20A O1A -178.4(5) . . . .
C14A C15A C20A O1A -0.9(6) . . . .
N2A C10A C21A C22A 36.3(7) . . . .
C11A C10A C21A C22A -76.5(6) . . . .
N2A C10A C21A C26A -148.0(5) . . . .
C11A C10A C21A C26A 99.2(6) . . . .
C26A C21A C22A C23A 0.4(8) . . . .
C10A C21A C22A C23A 176.1(5) . . . .
C21A C22A C23A C24A -0.2(8) . . . .
C22A C23A C24A C25A 0.3(8) . . . .
C23A C24A C25A C26A -0.7(8) . . . .
C24A C25A C26A C21A 0.9(8) . . . .
C22A C21A C26A C25A -0.7(8) . . . .
C10A C21A C26A C25A -176.6(5) . . . .
