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#$Date: 2022-05-04 12:14:49 +0300 (Wed, 04 May 2022) $
#$Revision: 274886 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105143.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_8105143
loop_
_publ_author_name
'Alotibi, Mohammed F.'
'Abdel-Wahab, Bakr F.'
'Yousif, Emad'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
'El-Hiti, Gamal A.'
_publ_section_title
;
 Crystal structure of
 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one,
 C28H20FN3O2S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              469
_journal_page_last               471
_journal_paper_doi               10.1515/ncrs-2019-0776
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C28 H20 F N3 O2 S'
_chemical_formula_sum            'C28 H20 F N3 O2 S'
_chemical_formula_weight         481.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                74.682(7)
_cell_angle_beta                 84.253(6)
_cell_angle_gamma                76.720(7)
_cell_formula_units_Z            2
_cell_length_a                   9.1325(7)
_cell_length_b                   11.5184(9)
_cell_length_c                   11.6535(9)
_cell_measurement_reflns_used    2029
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.2680
_cell_measurement_theta_min      4.7990
_cell_volume                     1149.67(16)
_computing_cell_refinement       'CrysAlis PRO [1]'
_computing_data_collection       'CrysAlis PRO [1]'
_computing_data_reduction        'CrysAlis PRO [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'ORTEP-3 for Windows [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXS [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8916
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         3.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41g (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration 
over a multifaceted crystal model. Empirical absorption correction 
using spherical harmonics, implemented in SCALE3 ABSPACK scaling 
algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0574
_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)+(0.0445P)²+0.3294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3323
_reflns_number_total             5371
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0776_suppl.cif
_cod_data_source_block           bmk1635
_cod_database_code               8105143
_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   0.954
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.1169(3) 0.9835(2) 0.2910(2) 0.0435(5) Uani 1 1 d . . . . .
C2 C 0.1309(3) 1.1006(2) 0.3110(2) 0.0547(6) Uani 1 1 d . . . . .
C3 C -0.1315(3) 1.1361(2) 0.3741(2) 0.0501(6) Uani 1 1 d . . . . .
C4 C -0.1501(3) 1.0316(2) 0.3454(2) 0.0472(6) Uani 1 1 d . . . . .
C5 C -0.0192(3) 0.9543(2) 0.3071(2) 0.0456(6) Uani 1 1 d . . . . .
H5 H -0.028348 0.880682 0.292655 0.055 Uiso 1 1 calc R U . . .
C6 C -0.2495(3) 1.2147(3) 0.4163(2) 0.0643(7) Uani 1 1 d . . . . .
H6 H -0.233364 1.282813 0.437781 0.077 Uiso 1 1 calc R U . . .
C7 C -0.3903(4) 1.1906(3) 0.4259(3) 0.0735(9) Uani 1 1 d . . . . .
H7 H -0.470727 1.242712 0.454459 0.088 Uiso 1 1 calc R U . . .
C8 C -0.4148(3) 1.0899(3) 0.3938(3) 0.0716(8) Uani 1 1 d . . . . .
H8 H -0.511818 1.076008 0.397977 0.086 Uiso 1 1 calc R U . . .
C9 C -0.2958(3) 1.0103(3) 0.3556(2) 0.0634(7) Uani 1 1 d . . . . .
H9 H -0.312440 0.941127 0.336331 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2511(3) 0.9040(2) 0.2520(2) 0.0447(5) Uani 1 1 d . . . . .
C11 C 0.3852(3) 0.9331(2) 0.2113(2) 0.0584(7) Uani 1 1 d . . . . .
H11 H 0.407209 1.009785 0.203622 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3697(3) 0.7263(2) 0.2201(2) 0.0434(5) Uani 1 1 d . . . . .
C13 C 0.2927(3) 0.5250(2) 0.2330(2) 0.0438(5) Uani 1 1 d . . . . .
H13 H 0.202208 0.567602 0.188277 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3852(3) 0.4229(2) 0.1757(2) 0.0481(6) Uani 1 1 d . . . . .
H14A H 0.387672 0.341846 0.228688 0.058 Uiso 1 1 calc R U . . .
H14B H 0.344204 0.426431 0.100930 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5387(3) 0.4522(2) 0.15642(19) 0.0438(5) Uani 1 1 d . . . . .
C16 C 0.2500(2) 0.47624(19) 0.36272(19) 0.0408(5) Uani 1 1 d . . . . .
C17 C 0.3128(3) 0.4993(2) 0.4549(2) 0.0474(6) Uani 1 1 d . . . . .
H17 H 0.383503 0.548820 0.438136 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2720(3) 0.4497(2) 0.5725(2) 0.0548(6) Uani 1 1 d . . . . .
H18 H 0.314053 0.465710 0.634665 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1696(3) 0.3774(2) 0.5946(2) 0.0550(6) Uani 1 1 d . . . . .
C20 C 0.1048(3) 0.3507(2) 0.5069(2) 0.0589(7) Uani 1 1 d . . . . .
H20 H 0.035000 0.300331 0.524899 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1464(3) 0.4010(2) 0.3908(2) 0.0528(6) Uani 1 1 d . . . . .
H21 H 0.103771 0.383927 0.329463 0.063 Uiso 1 1 calc R U . . .
C22 C 0.6760(3) 0.3764(2) 0.1166(2) 0.0486(6) Uani 1 1 d . . . . .
C23 C 0.8139(3) 0.4104(3) 0.1098(2) 0.0622(7) Uani 1 1 d . . . . .
H23 H 0.819715 0.480260 0.133403 0.075 Uiso 1 1 calc R U . . .
C24 C 0.9424(3) 0.3410(3) 0.0681(3) 0.0724(8) Uani 1 1 d . . . . .
H24 H 1.033761 0.365002 0.063679 0.087 Uiso 1 1 calc R U . . .
C25 C 0.9373(4) 0.2365(3) 0.0328(2) 0.0667(8) Uani 1 1 d . . . . .
C26 C 0.8015(4) 0.2030(3) 0.0418(2) 0.0683(8) Uani 1 1 d . . . . .
H26 H 0.796548 0.132282 0.019511 0.082 Uiso 1 1 calc R U . . .
C27 C 0.6710(3) 0.2712(2) 0.0831(2) 0.0579(7) Uani 1 1 d . . . . .
H27 H 0.580369 0.245967 0.088105 0.069 Uiso 1 1 calc R U . . .
C28 C 1.0790(4) 0.1634(3) -0.0156(3) 0.0968(12) Uani 1 1 d . . . . .
H28A H 1.162152 0.201258 -0.014856 0.145 Uiso 0.5 1 calc R U P . .
H28B H 1.099749 0.080646 0.033328 0.145 Uiso 0.5 1 calc R U P . .
H28C H 1.064672 0.162218 -0.095685 0.145 Uiso 0.5 1 calc R U P . .
H28D H 1.055563 0.094824 -0.036619 0.145 Uiso 0.5 1 calc R U P . .
H28E H 1.117966 0.215436 -0.084803 0.145 Uiso 0.5 1 calc R U P . .
H28F H 1.153043 0.133863 0.044209 0.145 Uiso 0.5 1 calc R U P . .
N1 N 0.2415(2) 0.78356(16) 0.25686(16) 0.0446(5) Uani 1 1 d . . . . .
N2 N 0.3994(2) 0.60672(17) 0.21527(17) 0.0482(5) Uani 1 1 d . . . . .
N3 N 0.5421(2) 0.55653(17) 0.17574(16) 0.0468(5) Uani 1 1 d . . . . .
O1 O 0.00688(19) 1.16673(15) 0.35960(17) 0.0607(5) Uani 1 1 d . . . . .
O2 O 0.2400(2) 1.14491(18) 0.2892(2) 0.0850(7) Uani 1 1 d . . . . .
S1 S 0.50975(8) 0.81025(6) 0.17575(7) 0.0622(2) Uani 1 1 d . . . . .
F1 F 0.1273(2) 0.33016(17) 0.70997(13) 0.0830(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 1 0 0.0691
12 -1 0 0.0691
-1 -15 2 0.0518
1 15 -2 0.0518
-1 -5 -16 0.1001
1 -2 15 0.1108
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
C5 C1 C2 118.8(2) . .
C5 C1 C10 122.56(19) . .
C2 C1 C10 118.7(2) . .
O2 C2 O1 116.4(2) . .
O2 C2 C1 126.5(2) . .
O1 C2 C1 117.1(2) . .
O1 C3 C6 117.2(2) . .
O1 C3 C4 120.6(2) . .
C6 C3 C4 122.3(2) . .
C3 C4 C9 117.3(2) . .
C3 C4 C5 117.5(2) . .
C9 C4 C5 125.2(2) . .
C1 C5 C4 122.7(2) . .
C1 C5 H5 118.7 . .
C4 C5 H5 118.7 . .
C7 C6 C3 118.8(3) . .
C7 C6 H6 120.6 . .
C3 C6 H6 120.6 . .
C6 C7 C8 120.8(3) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C9 C8 C7 119.8(3) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C8 C9 C4 120.9(3) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C11 C10 N1 115.3(2) . .
C11 C10 C1 127.6(2) . .
N1 C10 C1 117.06(19) . .
C10 C11 S1 111.27(17) . .
C10 C11 H11 124.4 . .
S1 C11 H11 124.4 . .
N1 C12 N2 124.1(2) . .
N1 C12 S1 116.75(16) . .
N2 C12 S1 119.20(17) . .
N2 C13 C16 113.06(18) . .
N2 C13 C14 100.45(16) . .
C16 C13 C14 112.57(18) . .
N2 C13 H13 110.1 . .
C16 C13 H13 110.1 . .
C14 C13 H13 110.1 . .
C15 C14 C13 102.98(17) . .
C15 C14 H14A 111.2 . .
C13 C14 H14A 111.2 . .
C15 C14 H14B 111.2 . .
C13 C14 H14B 111.2 . .
H14A C14 H14B 109.1 . .
N3 C15 C22 120.1(2) . .
N3 C15 C14 113.47(19) . .
C22 C15 C14 126.37(19) . .
C17 C16 C21 118.1(2) . .
C17 C16 C13 123.3(2) . .
C21 C16 C13 118.50(19) . .
C16 C17 C18 120.9(2) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C19 C18 C17 118.4(2) . .
C19 C18 H18 120.8 . .
C17 C18 H18 120.8 . .
C18 C19 F1 118.5(2) . .
C18 C19 C20 123.2(2) . .
F1 C19 C20 118.2(2) . .
C19 C20 C21 117.6(2) . .
C19 C20 H20 121.2 . .
C21 C20 H20 121.2 . .
C20 C21 C16 121.8(2) . .
C20 C21 H21 119.1 . .
C16 C21 H21 119.1 . .
C27 C22 C23 118.6(2) . .
C27 C22 C15 120.8(2) . .
C23 C22 C15 120.6(2) . .
C24 C23 C22 120.4(3) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C25 C24 C23 121.1(3) . .
C25 C24 H24 119.5 . .
C23 C24 H24 119.5 . .
C26 C25 C24 117.9(2) . .
C26 C25 C28 121.9(3) . .
C24 C25 C28 120.2(3) . .
C25 C26 C27 122.1(3) . .
C25 C26 H26 118.9 . .
C27 C26 H26 118.9 . .
C22 C27 C26 119.9(3) . .
C22 C27 H27 120.1 . .
C26 C27 H27 120.1 . .
C25 C28 H28A 109.5 . .
C25 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C25 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
H28D C28 H28E 109.5 . .
H28D C28 H28F 109.5 . .
H28E C28 H28F 109.5 . .
C12 N1 C10 108.85(18) . .
C12 N2 N3 118.05(18) . .
C12 N2 C13 127.77(19) . .
N3 N2 C13 113.72(16) . .
C15 N3 N2 108.14(19) . .
C3 O1 C2 122.75(18) . .
C11 S1 C12 87.82(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.343(3) .
C1 C2 1.463(3) .
C1 C10 1.463(3) .
C2 O2 1.197(3) .
C2 O1 1.374(3) .
C3 O1 1.372(3) .
C3 C6 1.379(3) .
C3 C4 1.381(3) .
C4 C9 1.396(3) .
C4 C5 1.427(3) .
C5 H5 0.9300 .
C6 C7 1.364(4) .
C6 H6 0.9300 .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.371(4) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C11 1.351(3) .
C10 N1 1.396(3) .
C11 S1 1.716(2) .
C11 H11 0.9300 .
C12 N1 1.298(3) .
C12 N2 1.357(3) .
C12 S1 1.735(2) .
C13 N2 1.468(3) .
C13 C16 1.512(3) .
C13 C14 1.546(3) .
C13 H13 0.9800 .
C14 C15 1.498(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 N3 1.287(3) .
C15 C22 1.464(3) .
C16 C17 1.378(3) .
C16 C21 1.386(3) .
C17 C18 1.387(3) .
C17 H17 0.9300 .
C18 C19 1.353(3) .
C18 H18 0.9300 .
C19 F1 1.364(3) .
C19 C20 1.364(4) .
C20 C21 1.377(3) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 C27 1.380(3) .
C22 C23 1.392(4) .
C23 C24 1.383(4) .
C23 H23 0.9300 .
C24 C25 1.382(4) .
C24 H24 0.9300 .
C25 C26 1.367(4) .
C25 C28 1.518(4) .
C26 C27 1.386(4) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C28 H28D 0.9600 .
C28 H28E 0.9600 .
C28 H28F 0.9600 .
N2 N3 1.385(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 O2 0.93 2.27 2.824(3) 117.3 . yes
C18 H18 N3 0.93 2.61 3.511(3) 163.8 2_666 yes
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.0000 1.0000 0.0000 -0.4004 0.7314 0.5042
12.0000 -1.0000 -0.0000 0.4004 -0.7314 -0.5042
-1.0000 -15.0000 2.0000 0.9770 0.1670 0.1721
1.0000 15.0000 -2.0000 -0.9770 -0.1670 -0.1721
-1.0000 -5.0000 -16.0000 -0.0914 -0.6152 0.7519
1.0000 -2.0000 15.0000 0.5142 0.5821 -0.6145
