##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/1'
_journal_date_recd_electronic     2019-03-13
_journal_date_accepted     2019-03-14
_journal_name_full     'IUCrData'
_journal_year     2019
_journal_volume     4
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314619003596
_journal_coeditor_code     HB4289
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Gamal A. El-Hiti'
;
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
 gelhiti@ksu.edu.sa
    'Kariuki, Benson M.'
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
 kariukib@cardiff.ac.uk
_publ_contact_author_fax     '00966114693536'
_publ_contact_author_phone     '00966114693778'
_publ_section_title
;\
4-(Benzofuran-2-yl)-2-[3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-\
1H-pyrazol-1-yl]thiazole
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Hiti, Gamal A.' .
;
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
    'Abdel-Wahab, Bakr F.' .
;
Department of Chemistry
College of Science and Humanities
Shaqra University
Duwadimi
Saudi Arabia
Applied Organic Chemistry Department
National Research Centre
Dokki
Giza
Egypt
;
    'Alqahtani, Alaa' .
;
Pharmaceutical Chemistry Department
College of Pharmacy
Umm Al-Qura University
Makkah
Saudi Arabia
;
    'Hegazy, Amany S.' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
    'Kariuki, Benson M.'
;
Additional corresponding author
;
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
Wales
;
_publ_section_synopsis
;
In the molecule of the title compound, pairwise C---H...F interactions link the
molecules into inversion dimers. Aromatic π--π interactions occur between
rings of neighbouring pairs of molecules related by inversion symmetry are
also observed. Taken together, the weak interactions generate [010] chains.
;
_chemical_name_systematic
;\
4-(Benzofuran-2-yl)-2-[3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-\
1H-pyrazol-1-yl]thiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H17 Cl F N3 O S'
_chemical_formula_sum     'C26 H17 Cl F N3 O S'
_chemical_formula_iupac     'C26 H17 Cl F N3 O S'
_chemical_formula_weight     473.93
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     6.6631(6)
_cell_length_b     15.2297(17)
_cell_length_c     22.431(3)
_cell_angle_alpha     90
_cell_angle_beta     96.390(9)
_cell_angle_gamma     90
_cell_volume     2262.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1999
_cell_measurement_theta_min     3.7320
_cell_measurement_theta_max     23.2950
_cell_measurement_temperature     296(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.460
_exptl_crystal_size_mid     0.189
_exptl_crystal_size_min     0.113
_exptl_crystal_density_diffrn     1.392
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.294
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_absorpt_correction_T_min     0.990
_exptl_absorpt_correction_T_max     0.997
_diffrn_ambient_temperature     296(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
         'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10799
_diffrn_reflns_av_R_equivalents     0.0418
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_theta_min     3.355
_diffrn_reflns_theta_max     26.372
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     4617
_reflns_number_gt     2323
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1247
_refine_ls_R_factor_gt     0.0603
_refine_ls_wR_factor_gt     0.1345
_refine_ls_wR_factor_ref     0.1708
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     4617
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0542P)²+0.6825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.169
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows and WinGX (Farrugia, 2012)
;
_computing_publication_material
;
ORTEP-3 for Windows and WinGX (Farrugia, 2012), and
CHEMDRAW Ultra (Cambridge Soft, 2001)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 -0.0420(5) 0.9153(2) 0.16557(14) 0.0617(8) Uani d 1 . .
    C C2 -0.2264(5) 0.8840(2) 0.17209(15) 0.0666(9) Uani d 1 . .
    H H2 -0.315276 0.858931 0.141930 0.080 Uiso calc 1 . .
    C C3 -0.2636(5) 0.8956(2) 0.23330(15) 0.0659(9) Uani d 1 . .
    C C4 -0.0873(5) 0.9353(2) 0.26072(16) 0.0669(9) Uani d 1 . .
    C C5 -0.4193(6) 0.8785(3) 0.26796(18) 0.0805(11) Uani d 1 . .
    H H5 -0.538290 0.852152 0.251208 0.097 Uiso calc 1 . .
    C C6 -0.3937(7) 0.9014(3) 0.32729(19) 0.0923(12) Uani d 1 . .
    H H6 -0.497815 0.891053 0.350794 0.111 Uiso calc 1 . .
    C C7 -0.2172(8) 0.9393(3) 0.35304(18) 0.0948(13) Uani d 1 . .
    H H7 -0.204363 0.952927 0.393693 0.114 Uiso calc 1 . .
    C C8 -0.0587(7) 0.9576(3) 0.32022(18) 0.0898(12) Uani d 1 . .
    H H8 0.060249 0.983506 0.337468 0.108 Uiso calc 1 . .
    C C9 0.0725(5) 0.9187(2) 0.11473(14) 0.0591(8) Uani d 1 . .
    C C10 0.2685(5) 0.9408(2) 0.11469(16) 0.0712(10) Uani d 1 . .
    H H10 0.351786 0.959633 0.148300 0.085 Uiso calc 1 . .
    C C11 0.1001(5) 0.8959(2) 0.01989(16) 0.0637(8) Uani d 1 . .
    C C12 -0.1510(5) 0.8293(2) -0.05800(15) 0.0661(9) Uani d 1 . .
    H H12 -0.261981 0.869744 -0.052668 0.079 Uiso calc 1 . .
    C C13 -0.1304(5) 0.8178(3) -0.12471(15) 0.0810(11) Uani d 1 . .
    H H13A -0.154473 0.757287 -0.137032 0.097 Uiso calc 1 . .
    H H13B -0.224552 0.855387 -0.148931 0.097 Uiso calc 1 . .
    C C14 0.0830(5) 0.8439(2) -0.13025(15) 0.0601(8) Uani d 1 . .
    C C15 -0.1805(5) 0.7438(2) -0.02572(14) 0.0602(8) Uani d 1 . .
    C C16 -0.0221(6) 0.6941(3) 0.00002(18) 0.0819(11) Uani d 1 . .
    H H16 0.109071 0.713957 -0.001787 0.098 Uiso calc 1 . .
    C C17 -0.0516(6) 0.6161(3) 0.02832(19) 0.0900(12) Uani d 1 . .
    H H17 0.057272 0.583478 0.045913 0.108 Uiso calc 1 . .
    C C18 -0.2429(8) 0.5880(3) 0.02992(16) 0.0842(12) Uani d 1 . .
    C C19 -0.4061(6) 0.6335(3) 0.00476(17) 0.0840(12) Uani d 1 . .
    H H19 -0.536128 0.611895 0.005850 0.101 Uiso calc 1 . .
    C C20 -0.3735(5) 0.7132(3) -0.02265(15) 0.0706(10) Uani d 1 . .
    H H20 -0.483302 0.746331 -0.039096 0.085 Uiso calc 1 . .
    C C21 0.1776(5) 0.8416(2) -0.18589(14) 0.0599(8) Uani d 1 . .
    C C22 0.0785(6) 0.8020(2) -0.23703(17) 0.0777(10) Uani d 1 . .
    H H22 -0.047482 0.776451 -0.235296 0.093 Uiso calc 1 . .
    C C23 0.1650(7) 0.8002(3) -0.29021(18) 0.0883(12) Uani d 1 . .
    H H23 0.097113 0.774069 -0.324130 0.106 Uiso calc 1 . .
    C C24 0.3519(6) 0.8371(3) -0.29268(17) 0.0790(11) Uani d 1 . .
    C C25 0.4505(5) 0.8776(3) -0.24365(18) 0.0794(11) Uani d 1 . .
    H H25 0.575572 0.903742 -0.245998 0.095 Uiso calc 1 . .
    C C26 0.3637(5) 0.8797(2) -0.19036(16) 0.0706(9) Uani d 1 . .
    H H26 0.431759 0.907147 -0.157005 0.085 Uiso calc 1 . .
    N N1 -0.0258(4) 0.89273(19) 0.06012(12) 0.0645(7) Uani d 1 . .
    N N3 0.0437(4) 0.8709(2) -0.03768(13) 0.0748(8) Uani d 1 . .
    N N4 0.1770(4) 0.87408(18) -0.08051(12) 0.0629(7) Uani d 1 . .
    O O1 0.0500(3) 0.94806(16) 0.21956(10) 0.0709(6) Uani d 1 . .
    Cl Cl1 0.4626(2) 0.83256(9) -0.35884(5) 0.1214(5) Uani d 1 . .
    F F1 -0.2761(5) 0.51028(17) 0.05775(12) 0.1259(10) Uani d 1 . .
    S S1 0.34414(13) 0.92974(7) 0.04410(4) 0.0766(3) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.341(4) ?
    C1 O1 . 1.388(4) ?
    C1 C9 . 1.442(4) ?
    C2 C3 . 1.433(4) ?
    C2 H2 . 0.9300 ?
    C3 C5 . 1.389(5) ?
    C3 C4 . 1.401(5) ?
    C4 C8 . 1.370(5) ?
    C4 O1 . 1.384(4) ?
    C5 C6 . 1.368(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.378(6) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.381(6) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.350(4) ?
    C9 N1 . 1.381(4) ?
    C10 S1 . 1.722(4) ?
    C10 H10 . 0.9300 ?
    C11 N1 . 1.300(4) ?
    C11 N3 . 1.359(4) ?
    C11 S1 . 1.734(3) ?
    C12 N3 . 1.470(4) ?
    C12 C15 . 1.513(5) ?
    C12 C13 . 1.528(5) ?
    C12 H12 . 0.9800 ?
    C13 C14 . 1.495(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 N4 . 1.301(4) ?
    C14 C21 . 1.460(4) ?
    C15 C16 . 1.372(5) ?
    C15 C20 . 1.377(4) ?
    C16 C17 . 1.372(5) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.349(5) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.358(5) ?
    C18 F1 . 1.367(4) ?
    C19 C20 . 1.389(5) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
    C21 C26 . 1.383(4) ?
    C21 C22 . 1.396(5) ?
    C22 C23 . 1.382(5) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.373(5) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.365(5) ?
    C24 Cl1 . 1.731(4) ?
    C25 C26 . 1.385(5) ?
    C25 H25 . 0.9300 ?
    C26 H26 . 0.9300 ?
    N3 N4 . 1.380(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 O1 . . 110.7(3) ?
    C2 C1 C9 . . 132.1(3) ?
    O1 C1 C9 . . 117.1(3) ?
    C1 C2 C3 . . 108.6(3) ?
    C1 C2 H2 . . 125.7 ?
    C3 C2 H2 . . 125.7 ?
    C5 C3 C4 . . 118.5(3) ?
    C5 C3 C2 . . 137.1(4) ?
    C4 C3 C2 . . 104.4(3) ?
    C8 C4 O1 . . 125.8(4) ?
    C8 C4 C3 . . 123.6(4) ?
    O1 C4 C3 . . 110.6(3) ?
    C6 C5 C3 . . 118.5(4) ?
    C6 C5 H5 . . 120.7 ?
    C3 C5 H5 . . 120.7 ?
    C5 C6 C7 . . 121.5(4) ?
    C5 C6 H6 . . 119.3 ?
    C7 C6 H6 . . 119.3 ?
    C6 C7 C8 . . 121.9(4) ?
    C6 C7 H7 . . 119.0 ?
    C8 C7 H7 . . 119.0 ?
    C4 C8 C7 . . 115.9(4) ?
    C4 C8 H8 . . 122.0 ?
    C7 C8 H8 . . 122.0 ?
    C10 C9 N1 . . 115.8(3) ?
    C10 C9 C1 . . 127.4(3) ?
    N1 C9 C1 . . 116.8(3) ?
    C9 C10 S1 . . 111.0(3) ?
    C9 C10 H10 . . 124.5 ?
    S1 C10 H10 . . 124.5 ?
    N1 C11 N3 . . 121.2(3) ?
    N1 C11 S1 . . 116.7(3) ?
    N3 C11 S1 . . 122.1(3) ?
    N3 C12 C15 . . 112.3(3) ?
    N3 C12 C13 . . 100.4(3) ?
    C15 C12 C13 . . 113.6(3) ?
    N3 C12 H12 . . 110.1 ?
    C15 C12 H12 . . 110.1 ?
    C13 C12 H12 . . 110.1 ?
    C14 C13 C12 . . 103.9(3) ?
    C14 C13 H13A . . 111.0 ?
    C12 C13 H13A . . 111.0 ?
    C14 C13 H13B . . 111.0 ?
    C12 C13 H13B . . 111.0 ?
    H13A C13 H13B . . 109.0 ?
    N4 C14 C21 . . 122.0(3) ?
    N4 C14 C13 . . 113.2(3) ?
    C21 C14 C13 . . 124.7(3) ?
    C16 C15 C20 . . 118.1(3) ?
    C16 C15 C12 . . 122.7(3) ?
    C20 C15 C12 . . 119.1(3) ?
    C17 C16 C15 . . 121.9(4) ?
    C17 C16 H16 . . 119.0 ?
    C15 C16 H16 . . 119.0 ?
    C18 C17 C16 . . 118.1(4) ?
    C18 C17 H17 . . 120.9 ?
    C16 C17 H17 . . 120.9 ?
    C17 C18 C19 . . 122.8(4) ?
    C17 C18 F1 . . 119.2(4) ?
    C19 C18 F1 . . 118.0(4) ?
    C18 C19 C20 . . 118.3(4) ?
    C18 C19 H19 . . 120.9 ?
    C20 C19 H19 . . 120.9 ?
    C15 C20 C19 . . 120.7(4) ?
    C15 C20 H20 . . 119.7 ?
    C19 C20 H20 . . 119.7 ?
    C26 C21 C22 . . 117.9(3) ?
    C26 C21 C14 . . 121.9(3) ?
    C22 C21 C14 . . 120.2(3) ?
    C23 C22 C21 . . 120.9(3) ?
    C23 C22 H22 . . 119.5 ?
    C21 C22 H22 . . 119.5 ?
    C24 C23 C22 . . 119.6(4) ?
    C24 C23 H23 . . 120.2 ?
    C22 C23 H23 . . 120.2 ?
    C25 C24 C23 . . 120.7(3) ?
    C25 C24 Cl1 . . 119.7(3) ?
    C23 C24 Cl1 . . 119.6(3) ?
    C24 C25 C26 . . 119.7(4) ?
    C24 C25 H25 . . 120.1 ?
    C26 C25 H25 . . 120.1 ?
    C21 C26 C25 . . 121.2(3) ?
    C21 C26 H26 . . 119.4 ?
    C25 C26 H26 . . 119.4 ?
    C11 N1 C9 . . 109.0(3) ?
    C11 N3 N4 . . 121.3(3) ?
    C11 N3 C12 . . 123.9(3) ?
    N4 N3 C12 . . 114.4(3) ?
    C14 N4 N3 . . 107.4(3) ?
    C4 O1 C1 . . 105.7(3) ?
    C10 S1 C11 . . 87.54(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C19 H19 F1 3_465 0.93 2.58 3.254(5) 130 yes
_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     0.877
_shelx_estimated_absorpt_T_max     0.968
