#------------------------------------------------------------------------------
#$Date: 2023-04-06 09:57:40 +0300 (Thu, 06 Apr 2023) $
#$Revision: 282455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107046.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_8107046
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Baashen, Mohammed'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of
 2-(3-(benzofuran-2-yl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-chlorophenyl)thiazole,
 C26H17ClFN3OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              911
_journal_page_last               912
_journal_paper_doi               10.1515/ncrs-2016-0004
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C26 H17 Cl F N3 O S'
_chemical_formula_weight         473.93
_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
_cell_angle_alpha                90
_cell_angle_beta                 94.5680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4955(2)
_cell_length_b                   14.6143(5)
_cell_length_c                   22.6492(8)
_cell_measurement_reflns_used    7222
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.93
_cell_measurement_theta_min      2.28
_cell_volume                     2143.20(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.992
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30786
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.592
_diffrn_reflns_theta_min         2.788
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.547
_exptl_crystal_size_mid          0.458
_exptl_crystal_size_min          0.365
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         7755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0461
_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)+(0.0456P)²+0.8778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5610
_reflns_number_total             7755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0004_suppl.cif
_cod_data_source_block           sa34
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107046
_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   0.849
_shelx_estimated_absorpt_t_max   0.895
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
Cl1 Cl 0.89879(6) 0.92371(3) 0.14875(2) 0.02728(9) Uani 1 1 d . . . . .
S1 S 0.16442(5) 0.94663(3) 0.44387(2) 0.01931(8) Uani 1 1 d . . . . .
F1 F 0.73286(14) 0.46836(6) 0.42524(4) 0.0290(2) Uani 1 1 d . . . . .
O1 O 0.14074(14) 0.85116(7) 0.66855(4) 0.01721(19) Uani 1 1 d . . . . .
N1 N 0.32568(17) 0.86227(8) 0.55935(5) 0.0178(2) Uani 1 1 d . . . . .
N2 N 0.46026(18) 0.86166(9) 0.51510(5) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.52699(17) 0.89250(8) 0.41772(5) 0.0175(2) Uani 1 1 d . . . . .
C1 C 0.3385(2) 0.81899(9) 0.66240(6) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.4275(2) 0.78481(9) 0.71403(6) 0.0167(2) Uani 1 1 d . . . . .
H2A H 0.5610 0.7583 0.7203 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2799(2) 0.79672(9) 0.75738(6) 0.0159(2) Uani 1 1 d . . . . .
C4 C 0.2761(2) 0.77883(10) 0.81808(6) 0.0195(3) Uani 1 1 d . . . . .
H4A H 0.3925 0.7530 0.8401 0.023 Uiso 1 1 calc R U . . .
C5 C 0.0986(2) 0.79975(10) 0.84498(6) 0.0223(3) Uani 1 1 d . . . . .
H5A H 0.0934 0.7878 0.8861 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0742(2) 0.83815(10) 0.81311(6) 0.0220(3) Uani 1 1 d . . . . .
H6A H -0.1945 0.8511 0.8328 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0721(2) 0.85755(10) 0.75317(6) 0.0191(3) Uani 1 1 d . . . . .
H7A H -0.1880 0.8839 0.7312 0.023 Uiso 1 1 calc R U . . .
C8 C 0.1074(2) 0.83660(9) 0.72706(6) 0.0158(2) Uani 1 1 d . . . . .
C9 C 0.4239(2) 0.82796(9) 0.60615(6) 0.0166(2) Uani 1 1 d . . . . .
C10 C 0.6445(2) 0.80127(11) 0.59801(6) 0.0211(3) Uani 1 1 d . . . . .
H10A H 0.6722 0.7371 0.6102 0.025 Uiso 1 1 calc R U . . .
H10B H 0.7434 0.8420 0.6208 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6565(2) 0.81357(10) 0.53069(6) 0.0187(3) Uani 1 1 d . . . . .
H11A H 0.7759 0.8537 0.5228 0.022 Uiso 1 1 calc R U . . .
C12 C 0.67185(19) 0.72325(10) 0.49883(6) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.8669(2) 0.68486(10) 0.49515(6) 0.0206(3) Uani 1 1 d . . . . .
H13A H 0.9862 0.7177 0.5100 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8884(2) 0.59909(11) 0.47003(6) 0.0224(3) Uani 1 1 d . . . . .
H14A H 1.0212 0.5728 0.4675 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7135(2) 0.55314(10) 0.44887(6) 0.0212(3) Uani 1 1 d . . . . .
C16 C 0.5174(2) 0.58931(11) 0.45078(6) 0.0233(3) Uani 1 1 d . . . . .
H16A H 0.3990 0.5566 0.4351 0.028 Uiso 1 1 calc R U . . .
C17 C 0.4988(2) 0.67496(11) 0.47633(6) 0.0215(3) Uani 1 1 d . . . . .
H17A H 0.3656 0.7010 0.4785 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4045(2) 0.89612(9) 0.46053(6) 0.0169(3) Uani 1 1 d . . . . .
C19 C 0.2370(2) 0.96457(10) 0.37291(6) 0.0190(3) Uani 1 1 d . . . . .
H19A H 0.1528 0.9936 0.3422 0.023 Uiso 1 1 calc R U . . .
C20 C 0.4307(2) 0.93164(9) 0.36684(6) 0.0159(2) Uani 1 1 d . . . . .
C21 C 0.5424(2) 0.93008(9) 0.31278(6) 0.0160(2) Uani 1 1 d . . . . .
C22 C 0.4496(2) 0.95771(10) 0.25775(6) 0.0210(3) Uani 1 1 d . . . . .
H22A H 0.3100 0.9777 0.2549 0.025 Uiso 1 1 calc R U . . .
C23 C 0.5580(2) 0.95651(10) 0.20727(6) 0.0227(3) Uani 1 1 d . . . . .
H23A H 0.4943 0.9767 0.1703 0.027 Uiso 1 1 calc R U . . .
C25 C 0.8536(2) 0.89421(10) 0.26471(6) 0.0213(3) Uani 1 1 d . . . . .
H25A H 0.9906 0.8710 0.2668 0.026 Uiso 1 1 calc R U . . .
C24 C 0.7601(2) 0.92542(10) 0.21153(6) 0.0200(3) Uani 1 1 d . . . . .
C26 C 0.7446(2) 0.89717(10) 0.31515(6) 0.0198(3) Uani 1 1 d . . . . .
H26A H 0.8089 0.8764 0.3519 0.024 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C19 S1 C18 87.71(6) . .
C8 O1 C1 105.24(10) . .
C9 N1 N2 107.01(11) . .
C18 N2 N1 121.34(11) . .
C18 N2 C11 123.94(11) . .
N1 N2 C11 114.49(10) . .
C18 N3 C20 109.82(11) . .
C2 C1 O1 111.88(11) . .
C2 C1 C9 129.04(12) . .
O1 C1 C9 119.04(11) . .
C1 C2 C3 106.42(12) . .
C1 C2 H2A 126.8 . .
C3 C2 H2A 126.8 . .
C8 C3 C4 119.00(12) . .
C8 C3 C2 105.55(11) . .
C4 C3 C2 135.45(13) . .
C5 C4 C3 118.17(13) . .
C5 C4 H4A 120.9 . .
C3 C4 H4A 120.9 . .
C4 C5 C6 121.58(13) . .
C4 C5 H5A 119.2 . .
C6 C5 H5A 119.2 . .
C7 C6 C5 121.03(13) . .
C7 C6 H6A 119.5 . .
C5 C6 H6A 119.5 . .
C8 C7 C6 116.57(13) . .
C8 C7 H7A 121.7 . .
C6 C7 H7A 121.7 . .
O1 C8 C7 125.47(12) . .
O1 C8 C3 110.90(11) . .
C7 C8 C3 123.63(12) . .
N1 C9 C1 124.20(12) . .
N1 C9 C10 114.26(11) . .
C1 C9 C10 121.48(11) . .
C9 C10 C11 102.32(11) . .
C9 C10 H10A 111.3 . .
C11 C10 H10A 111.3 . .
C9 C10 H10B 111.3 . .
C11 C10 H10B 111.3 . .
H10A C10 H10B 109.2 . .
N2 C11 C12 113.00(11) . .
N2 C11 C10 100.47(10) . .
C12 C11 C10 112.36(12) . .
N2 C11 H11A 110.2 . .
C12 C11 H11A 110.2 . .
C10 C11 H11A 110.2 . .
C17 C12 C13 119.08(13) . .
C17 C12 C11 122.45(12) . .
C13 C12 C11 118.35(12) . .
C14 C13 C12 120.64(14) . .
C14 C13 H13A 119.7 . .
C12 C13 H13A 119.7 . .
C15 C14 C13 118.50(13) . .
C15 C14 H14A 120.7 . .
C13 C14 H14A 120.7 . .
F1 C15 C14 118.89(13) . .
F1 C15 C16 118.37(13) . .
C14 C15 C16 122.74(14) . .
C15 C16 C17 117.93(14) . .
C15 C16 H16A 121.0 . .
C17 C16 H16A 121.0 . .
C16 C17 C12 121.10(13) . .
C16 C17 H17A 119.4 . .
C12 C17 H17A 119.4 . .
N3 C18 N2 121.89(12) . .
N3 C18 S1 116.46(10) . .
N2 C18 S1 121.65(10) . .
C20 C19 S1 111.20(10) . .
C20 C19 H19A 124.4 . .
S1 C19 H19A 124.4 . .
C19 C20 N3 114.81(12) . .
C19 C20 C21 127.51(12) . .
N3 C20 C21 117.63(11) . .
C26 C21 C22 118.07(12) . .
C26 C21 C20 119.87(12) . .
C22 C21 C20 122.02(12) . .
C23 C22 C21 121.25(13) . .
C23 C22 H22A 119.4 . .
C21 C22 H22A 119.4 . .
C24 C23 C22 119.07(13) . .
C24 C23 H23A 120.5 . .
C22 C23 H23A 120.5 . .
C24 C25 C26 119.22(13) . .
C24 C25 H25A 120.4 . .
C26 C25 H25A 120.4 . .
C25 C24 C23 121.13(13) . .
C25 C24 Cl1 119.11(11) . .
C23 C24 Cl1 119.75(11) . .
C25 C26 C21 121.18(13) . .
C25 C26 H26A 119.4 . .
C21 C26 H26A 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C24 1.7432(14) .
S1 C19 1.7305(14) .
S1 C18 1.7395(14) .
F1 C15 1.3594(17) .
O1 C8 1.3763(15) .
O1 C1 1.3854(15) .
N1 C9 1.2941(17) .
N1 N2 1.3813(15) .
N2 C18 1.3568(17) .
N2 C11 1.4736(17) .
N3 C18 1.3034(17) .
N3 C20 1.3898(17) .
C1 C2 1.3578(18) .
C1 C9 1.4354(18) .
C2 C3 1.4364(18) .
C2 H2A 0.9500 .
C3 C8 1.3943(18) .
C3 C4 1.4016(18) .
C4 C5 1.381(2) .
C4 H4A 0.9500 .
C5 C6 1.402(2) .
C5 H5A 0.9500 .
C6 C7 1.388(2) .
C6 H6A 0.9500 .
C7 C8 1.3827(18) .
C7 H7A 0.9500 .
C9 C10 1.5104(18) .
C10 C11 1.5434(18) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.512(2) .
C11 H11A 1.0000 .
C12 C17 1.389(2) .
C12 C13 1.3941(18) .
C13 C14 1.388(2) .
C13 H13A 0.9500 .
C14 C15 1.373(2) .
C14 H14A 0.9500 .
C15 C16 1.383(2) .
C16 C17 1.388(2) .
C16 H16A 0.9500 .
C17 H17A 0.9500 .
C19 C20 1.3642(19) .
C19 H19A 0.9500 .
C20 C21 1.4724(18) .
C21 C26 1.3954(19) .
C21 C22 1.4000(18) .
C22 C23 1.3895(19) .
C22 H22A 0.9500 .
C23 C24 1.386(2) .
C23 H23A 0.9500 .
C25 C24 1.382(2) .
C25 C26 1.3920(19) .
C25 H25A 0.9500 .
C26 H26A 0.9500 .
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
C9 N1 N2 C18 -178.02(13) . . . .
C9 N1 N2 C11 7.38(16) . . . .
C8 O1 C1 C2 0.48(15) . . . .
C8 O1 C1 C9 -177.45(12) . . . .
O1 C1 C2 C3 -1.06(16) . . . .
C9 C1 C2 C3 176.60(14) . . . .
C1 C2 C3 C8 1.21(15) . . . .
C1 C2 C3 C4 -178.09(15) . . . .
C8 C3 C4 C5 1.5(2) . . . .
C2 C3 C4 C5 -179.31(15) . . . .
C3 C4 C5 C6 -0.2(2) . . . .
C4 C5 C6 C7 -0.7(2) . . . .
C5 C6 C7 C8 0.3(2) . . . .
C1 O1 C8 C7 -179.25(13) . . . .
C1 O1 C8 C3 0.34(14) . . . .
C6 C7 C8 O1 -179.47(13) . . . .
C6 C7 C8 C3 1.0(2) . . . .
C4 C3 C8 O1 178.47(12) . . . .
C2 C3 C8 O1 -0.96(15) . . . .
C4 C3 C8 C7 -1.9(2) . . . .
C2 C3 C8 C7 178.64(13) . . . .
N2 N1 C9 C1 178.26(13) . . . .
N2 N1 C9 C10 1.05(17) . . . .
C2 C1 C9 N1 -179.57(14) . . . .
O1 C1 C9 N1 -2.1(2) . . . .
C2 C1 C9 C10 -2.6(2) . . . .
O1 C1 C9 C10 174.96(12) . . . .
N1 C9 C10 C11 -8.16(17) . . . .
C1 C9 C10 C11 174.54(12) . . . .
C18 N2 C11 C12 -66.37(18) . . . .
N1 N2 C11 C12 108.07(13) . . . .
C18 N2 C11 C10 173.71(14) . . . .
N1 N2 C11 C10 -11.85(16) . . . .
C9 C10 C11 N2 10.86(14) . . . .
C9 C10 C11 C12 -109.52(12) . . . .
N2 C11 C12 C17 -23.12(18) . . . .
C10 C11 C12 C17 89.72(15) . . . .
N2 C11 C12 C13 160.76(12) . . . .
C10 C11 C12 C13 -86.40(15) . . . .
C17 C12 C13 C14 -0.8(2) . . . .
C11 C12 C13 C14 175.48(13) . . . .
C12 C13 C14 C15 0.1(2) . . . .
C13 C14 C15 F1 -178.75(12) . . . .
C13 C14 C15 C16 1.0(2) . . . .
F1 C15 C16 C17 178.43(12) . . . .
C14 C15 C16 C17 -1.3(2) . . . .
C15 C16 C17 C12 0.6(2) . . . .
C13 C12 C17 C16 0.4(2) . . . .
C11 C12 C17 C16 -175.65(13) . . . .
C20 N3 C18 N2 179.34(13) . . . .
C20 N3 C18 S1 -0.12(15) . . . .
N1 N2 C18 N3 -177.11(13) . . . .
C11 N2 C18 N3 -3.0(2) . . . .
N1 N2 C18 S1 2.3(2) . . . .
C11 N2 C18 S1 176.40(11) . . . .
C19 S1 C18 N3 -0.17(12) . . . .
C19 S1 C18 N2 -179.63(13) . . . .
C18 S1 C19 C20 0.41(11) . . . .
S1 C19 C20 N3 -0.58(16) . . . .
S1 C19 C20 C21 176.92(11) . . . .
C18 N3 C20 C19 0.45(17) . . . .
C18 N3 C20 C21 -177.31(12) . . . .
C19 C20 C21 C26 177.21(14) . . . .
N3 C20 C21 C26 -5.35(19) . . . .
C19 C20 C21 C22 -5.2(2) . . . .
N3 C20 C21 C22 172.27(13) . . . .
C26 C21 C22 C23 -2.9(2) . . . .
C20 C21 C22 C23 179.46(13) . . . .
C21 C22 C23 C24 1.4(2) . . . .
C26 C25 C24 C23 -2.3(2) . . . .
C26 C25 C24 Cl1 178.75(11) . . . .
C22 C23 C24 C25 1.2(2) . . . .
C22 C23 C24 Cl1 -179.81(11) . . . .
C24 C25 C26 C21 0.7(2) . . . .
C22 C21 C26 C25 1.8(2) . . . .
C20 C21 C26 C25 179.51(13) . . . .
