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#$Date: 2023-04-05 11:39:39 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107037.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_8107037
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Abdel-Wahab, Bakr F.'
'Baashen, Mohammed'
'Ghabbour, Hazem A.'
'Alruqi, Obaid S.'
_publ_section_title
;
 Crystal structure of
 3-(benzofuran-2-yl)-5-(4-fluorophenyl)-4,5-dihydro-1Hpyrazole-1-carbothioamide,
 C18H14FN3OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              887
_journal_page_last               888
_journal_paper_doi               10.1515/ncrs-2015-0304
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C18 H14 F N3 O S'
_chemical_formula_weight         339.38
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.331(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9084(6)
_cell_length_b                   11.2339(4)
_cell_length_c                   9.4417(4)
_cell_measurement_reflns_used    9041
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.66
_cell_measurement_theta_min      2.29
_cell_volume                     1544.81(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34811
_diffrn_reflns_theta_full        33.22
_diffrn_reflns_theta_max         33.22
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         34811
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0108(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0365
_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)+(0.0455P)²+0.8106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                4687
_reflns_number_total             5916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0304_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107037
loop_
_symmetry_equiv_pos_as_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
S1 S -0.00709(2) 0.66889(3) 0.34385(3) 0.01467(9) Uani 1 1 d . . . . .
F1 F 0.26018(6) 0.64126(8) -0.11869(8) 0.02247(19) Uani 1 1 d . . . . .
O1 O 0.35344(7) 0.37899(9) 0.75494(11) 0.0201(2) Uani 0.827(7) 1 d . . P A 1
N1 N 0.20148(7) 0.49118(10) 0.57633(11) 0.0142(2) Uani 1 1 d . . . . .
N2 N 0.13062(7) 0.52637(9) 0.46285(10) 0.0125(2) Uani 1 1 d . . . . .
N3 N 0.10302(8) 0.67892(10) 0.60586(12) 0.0171(2) Uani 1 1 d . . . . .
C1 C 0.41904(9) 0.29688(12) 0.81887(14) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.48917(11) 0.31332(14) 0.93856(16) 0.0265(3) Uani 1 1 d . . . . .
H2 H 0.4975 0.3870 0.9891 0.032 Uiso 1 1 calc R U . . .
C3 C 0.54659(10) 0.21769(16) 0.98141(16) 0.0309(4) Uani 1 1 d . . . . .
H3 H 0.5955 0.2254 1.0639 0.037 Uiso 1 1 calc R U . . .
C4 C 0.53459(11) 0.11067(16) 0.90679(19) 0.0332(4) Uani 1 1 d . . . . .
H4 H 0.5762 0.0472 0.9382 0.040 Uiso 1 1 calc R U . . .
C5 C 0.46346(11) 0.09388(13) 0.78764(18) 0.0282(3) Uani 1 1 d . . . . .
H5 H 0.4550 0.0198 0.7381 0.034 Uiso 1 1 calc R U . . .
C6 C 0.40436(9) 0.18985(12) 0.74268(14) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.32714(8) 0.20994(12) 0.62669(14) 0.0211(3) Uani 0.827(7) 1 d . . P A 1
H7 H 0.3000 0.1539 0.5550 0.025 Uiso 0.827(7) 1 calc R U P A 1
C8 C 0.30022(9) 0.32237(13) 0.63787(14) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.22666(8) 0.38614(11) 0.54501(13) 0.0141(2) Uani 1 1 d . . . . .
C10 C 0.17170(9) 0.33508(11) 0.40598(13) 0.0147(2) Uani 1 1 d . . . . .
H10A H 0.1299 0.2713 0.4248 0.018 Uiso 1 1 calc R U . . .
H10B H 0.2120 0.3033 0.3441 0.018 Uiso 1 1 calc R U . . .
C11 C 0.11771(8) 0.44552(10) 0.33655(12) 0.0119(2) Uani 1 1 d . . . . .
H11 H 0.0513 0.4258 0.3016 0.014 Uiso 1 1 calc R U . . .
C12 C 0.15669(8) 0.49908(10) 0.21516(12) 0.0112(2) Uani 1 1 d . . . . .
C13 C 0.23246(8) 0.57463(11) 0.24438(13) 0.0149(2) Uani 1 1 d . . . . .
H13 H 0.2599 0.5939 0.3420 0.018 Uiso 1 1 calc R U . . .
C14 C 0.26843(9) 0.62219(12) 0.13223(13) 0.0162(2) Uani 1 1 d . . . . .
H14 H 0.3200 0.6739 0.1517 0.019 Uiso 1 1 calc R U . . .
C15 C 0.22693(9) 0.59200(11) -0.00807(13) 0.0149(2) Uani 1 1 d . . . . .
C16 C 0.15248(9) 0.51661(11) -0.04208(13) 0.0158(2) Uani 1 1 d . . . . .
H16 H 0.1259 0.4971 -0.1399 0.019 Uiso 1 1 calc R U . . .
C17 C 0.11752(8) 0.47004(11) 0.07175(13) 0.0137(2) Uani 1 1 d . . . . .
H17 H 0.0663 0.4178 0.0514 0.016 Uiso 1 1 calc R U . . .
C18 C 0.07994(8) 0.62359(11) 0.47793(13) 0.0123(2) Uani 1 1 d . . . . .
H3A H 0.1485(13) 0.6547(16) 0.669(2) 0.027(5) Uiso 1 1 d . . . . .
H3B H 0.0725(13) 0.7394(17) 0.6220(19) 0.026(4) Uiso 1 1 d . . . . .
C1A C 0.35344(7) 0.37899(9) 0.75494(11) 0.0201(2) Uani 0.173(7) 1 d . . P A 2
H1A H 0.3467 0.4583 0.7859 0.024 Uiso 0.173(7) 1 calc R U P A 2
O7A O 0.32714(8) 0.20994(12) 0.62669(14) 0.0211(3) Uani 0.173(7) 1 d . . P A 2
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_
_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
C8 O1 C1 105.98(11) . .
C9 N1 N2 107.05(10) . .
C18 N2 N1 119.83(10) . .
C18 N2 C11 126.98(10) . .
N1 N2 C11 113.14(9) . .
C18 N3 H3A 120.2(13) . .
C18 N3 H3B 119.3(12) . .
H3A N3 H3B 120.5(17) . .
C2 C1 C1A 127.53(13) . .
C2 C1 O1 127.53(13) . .
C2 C1 C6 123.14(13) . .
C1A C1 C6 109.33(11) . .
O1 C1 C6 109.33(11) . .
C1 C2 C3 116.79(14) . .
C1 C2 H2 121.6 . .
C3 C2 H2 121.6 . .
C2 C3 C4 121.46(14) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C5 C4 C3 121.66(14) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C4 C5 C6 117.70(14) . .
C4 C5 H5 121.2 . .
C6 C5 H5 121.2 . .
C1 C6 C5 119.24(13) . .
C1 C6 O7A 105.76(12) . .
C5 C6 O7A 134.98(14) . .
C1 C6 C7 105.76(12) . .
C5 C6 C7 134.98(14) . .
C8 C7 C6 107.19(12) . .
C8 C7 H7 126.4 . .
C6 C7 H7 126.4 . .
C7 C8 O1 111.72(12) . .
O7A C8 C1A 111.72(12) . .
O7A C8 C9 128.66(13) . .
C7 C8 C9 128.66(13) . .
O1 C8 C9 119.62(12) . .
C1A C8 C9 119.62(12) . .
N1 C9 C8 122.40(12) . .
N1 C9 C10 114.66(11) . .
C8 C9 C10 122.92(11) . .
C9 C10 C11 101.60(10) . .
C9 C10 H10A 111.5 . .
C11 C10 H10A 111.5 . .
C9 C10 H10B 111.5 . .
C11 C10 H10B 111.5 . .
H10A C10 H10B 109.3 . .
N2 C11 C12 111.17(9) . .
N2 C11 C10 100.64(9) . .
C12 C11 C10 112.96(9) . .
N2 C11 H11 110.6 . .
C12 C11 H11 110.6 . .
C10 C11 H11 110.6 . .
C13 C12 C17 119.27(11) . .
C13 C12 C11 121.19(10) . .
C17 C12 C11 119.52(10) . .
C14 C13 C12 120.75(11) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C15 C14 C13 118.01(11) . .
C15 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
F1 C15 C16 118.47(11) . .
F1 C15 C14 118.26(11) . .
C16 C15 C14 123.27(11) . .
C15 C16 C17 117.80(11) . .
C15 C16 H16 121.1 . .
C17 C16 H16 121.1 . .
C16 C17 C12 120.89(11) . .
C16 C17 H17 119.6 . .
C12 C17 H17 119.6 . .
N3 C18 N2 115.39(11) . .
N3 C18 S1 123.13(10) . .
N2 C18 S1 121.47(9) . .
C8 C1A C1 105.98(11) . .
C8 C1A H1A 127.0 . .
C1 C1A H1A 127.0 . .
C8 O7A C6 107.19(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C18 1.6862(13) .
F1 C15 1.3653(13) .
O1 C8 1.3717(17) .
O1 C1 1.3855(16) .
N1 C9 1.2916(16) .
N1 N2 1.3917(14) .
N2 C18 1.3528(15) .
N2 C11 1.4785(15) .
N3 C18 1.3365(16) .
N3 H3A 0.85(2) .
N3 H3B 0.850(19) .
C1 C2 1.3782(19) .
C1 C1A 1.3855(16) .
C1 C6 1.3942(19) .
C2 C3 1.379(2) .
C2 H2 0.9500 .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C4 C5 1.384(2) .
C4 H4 0.9500 .
C5 C6 1.400(2) .
C5 H5 0.9500 .
C6 O7A 1.4272(17) .
C6 C7 1.4272(17) .
C7 C8 1.336(2) .
C7 H7 0.9500 .
C8 O7A 1.336(2) .
C8 C1A 1.3717(17) .
C8 C9 1.4401(17) .
C9 C10 1.5047(17) .
C10 C11 1.5464(17) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.5160(16) .
C11 H11 1.0000 .
C12 C13 1.3926(16) .
C12 C17 1.3939(16) .
C13 C14 1.3917(17) .
C13 H13 0.9500 .
C14 C15 1.3792(17) .
C14 H14 0.9500 .
C15 C16 1.3784(17) .
C16 C17 1.3927(17) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C1A H1A 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 168.27(10) . . . .
C9 N1 N2 C11 -9.50(13) . . . .
C8 O1 C1 C2 178.64(13) . . . .
C8 O1 C1 C6 -1.33(14) . . . .
C1A C1 C2 C3 -179.54(13) . . . .
O1 C1 C2 C3 -179.54(13) . . . .
C6 C1 C2 C3 0.4(2) . . . .
C1 C2 C3 C4 0.5(2) . . . .
C2 C3 C4 C5 -1.3(2) . . . .
C3 C4 C5 C6 1.1(2) . . . .
C2 C1 C6 C5 -0.6(2) . . . .
C1A C1 C6 C5 179.42(12) . . . .
O1 C1 C6 C5 179.42(12) . . . .
C2 C1 C6 O7A -179.12(12) . . . .
C1A C1 C6 O7A 0.86(14) . . . .
C2 C1 C6 C7 -179.12(12) . . . .
O1 C1 C6 C7 0.86(14) . . . .
C4 C5 C6 C1 -0.2(2) . . . .
C4 C5 C6 O7A 177.81(14) . . . .
C4 C5 C6 C7 177.81(14) . . . .
C1 C6 C7 C8 -0.04(14) . . . .
C5 C6 C7 C8 -178.26(15) . . . .
C6 C7 C8 O1 -0.81(14) . . . .
C6 C7 C8 C9 178.52(12) . . . .
C1 O1 C8 C7 1.34(14) . . . .
C1 O1 C8 C9 -178.06(11) . . . .
N2 N1 C9 C8 178.93(10) . . . .
N2 N1 C9 C10 -2.38(13) . . . .
O7A C8 C9 N1 172.57(13) . . . .
C7 C8 C9 N1 172.57(13) . . . .
O1 C8 C9 N1 -8.14(18) . . . .
C1A C8 C9 N1 -8.14(18) . . . .
O7A C8 C9 C10 -6.0(2) . . . .
C7 C8 C9 C10 -6.0(2) . . . .
O1 C8 C9 C10 173.28(11) . . . .
C1A C8 C9 C10 173.28(11) . . . .
N1 C9 C10 C11 12.16(13) . . . .
C8 C9 C10 C11 -169.16(11) . . . .
C18 N2 C11 C12 78.77(14) . . . .
N1 N2 C11 C12 -103.65(11) . . . .
C18 N2 C11 C10 -161.34(11) . . . .
N1 N2 C11 C10 16.25(12) . . . .
C9 C10 C11 N2 -15.49(11) . . . .
C9 C10 C11 C12 103.11(11) . . . .
N2 C11 C12 C13 31.31(15) . . . .
C10 C11 C12 C13 -80.96(14) . . . .
N2 C11 C12 C17 -150.27(11) . . . .
C10 C11 C12 C17 97.45(13) . . . .
C17 C12 C13 C14 0.78(18) . . . .
C11 C12 C13 C14 179.20(11) . . . .
C12 C13 C14 C15 -0.13(19) . . . .
C13 C14 C15 F1 178.03(11) . . . .
C13 C14 C15 C16 -0.6(2) . . . .
F1 C15 C16 C17 -178.00(11) . . . .
C14 C15 C16 C17 0.6(2) . . . .
C15 C16 C17 C12 0.07(19) . . . .
C13 C12 C17 C16 -0.75(18) . . . .
C11 C12 C17 C16 -179.20(11) . . . .
N1 N2 C18 N3 -0.40(16) . . . .
C11 N2 C18 N3 177.04(11) . . . .
N1 N2 C18 S1 -179.52(8) . . . .
C11 N2 C18 S1 -2.08(16) . . . .
O7A C8 C1A C1 1.34(14) . . . .
C9 C8 C1A C1 -178.06(11) . . . .
C2 C1 C1A C8 178.64(13) . . . .
C6 C1 C1A C8 -1.33(14) . . . .
C1A C8 O7A C6 -0.81(14) . . . .
C9 C8 O7A C6 178.52(12) . . . .
C1 C6 O7A C8 -0.04(14) . . . .
C5 C6 O7A C8 -178.26(15) . . . .
