#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/74/2237497.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237497
loop_
_publ_author_name
'Abdel-Wahab, Bakr F.'
'Mohamed, Hanan A.'
'Khidre, Rizk E.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
;
_journal_coeditor_code           HG5291
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o385
_journal_page_last               o386
_journal_paper_doi               10.1107/S1600536813004194
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C17 H16 F N3 S'
_chemical_formula_moiety         'C17 H16 F N3 S'
_chemical_formula_sum            'C17 H16 F N3 S'
_chemical_formula_weight         313.39
_chemical_name_systematic
5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.991(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4154(10)
_cell_length_b                   11.3197(9)
_cell_length_c                   9.5575(8)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5003
_cell_measurement_theta_min      2.9066
_cell_volume                     1513.3(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9303
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.2973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                2370
_reflns_number_total             3500
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5291.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237497
_cod_database_fobs_code          2237497
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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.48991(4) 0.33372(5) 0.33938(6) 0.04739(19) Uani d . 1 1
F F1 0.76993(11) 0.35963(12) -0.10409(14) 0.0659(4) Uani d . 1 1
N N1 0.63664(12) 0.46879(14) 0.46526(17) 0.0384(4) Uani d . 1 1
N N2 0.71143(11) 0.50005(15) 0.58117(17) 0.0391(4) Uani d . 1 1
N N3 0.60198(14) 0.32075(15) 0.60342(19) 0.0491(5) Uani d . 1 1
H H31 0.6497 0.3462 0.6727 0.059 Uiso calc R 1 1
H H32 0.5684 0.2591 0.6181 0.059 Uiso calc R 1 1
C C1 0.73573(16) 0.40770(19) 0.0050(2) 0.0445(5) Uani d . 1 1
C C2 0.77815(16) 0.3771(2) 0.1434(2) 0.0483(6) Uani d . 1 1
H H2 0.8306 0.3266 0.1637 0.058 Uiso calc R 1 1
C C3 0.74165(14) 0.42262(19) 0.2528(2) 0.0435(5) Uani d . 1 1
H H3 0.7697 0.4024 0.3479 0.052 Uiso calc R 1 1
C C4 0.66378(13) 0.49796(17) 0.2226(2) 0.0341(4) Uani d . 1 1
C C5 0.62418(15) 0.52828(18) 0.0812(2) 0.0416(5) Uani d . 1 1
H H5 0.5728 0.5804 0.0602 0.050 Uiso calc R 1 1
C C6 0.65938(16) 0.48273(19) -0.0307(2) 0.0469(5) Uani d . 1 1
H H6 0.6320 0.5025 -0.1262 0.056 Uiso calc R 1 1
C C7 0.62560(14) 0.55094(17) 0.3424(2) 0.0376(5) Uani d . 1 1
H H7 0.5584 0.5736 0.3066 0.045 Uiso calc R 1 1
C C8 0.68480(15) 0.65640(18) 0.4168(2) 0.0406(5) Uani d . 1 1
H H8A 0.7267 0.6865 0.3594 0.049 Uiso calc R 1 1
H H8B 0.6439 0.7198 0.4347 0.049 Uiso calc R 1 1
C C9 0.74100(14) 0.60325(18) 0.5553(2) 0.0378(5) Uani d . 1 1
C C10 0.82031(14) 0.65987(18) 0.6583(2) 0.0381(5) Uani d . 1 1
C C11 0.87678(15) 0.5981(2) 0.7726(2) 0.0486(6) Uani d . 1 1
H H11 0.8658 0.5179 0.7826 0.058 Uiso calc R 1 1
C C12 0.94914(17) 0.6537(2) 0.8718(3) 0.0526(6) Uani d . 1 1
H H12 0.9867 0.6101 0.9470 0.063 Uiso calc R 1 1
C C13 0.96669(15) 0.7734(2) 0.8614(2) 0.0470(5) Uani d . 1 1
C C14 0.91224(16) 0.8339(2) 0.7453(3) 0.0519(6) Uani d . 1 1
H H14 0.9243 0.9136 0.7342 0.062 Uiso calc R 1 1
C C15 0.83985(15) 0.7787(2) 0.6447(2) 0.0470(5) Uani d . 1 1
H H15 0.8041 0.8216 0.5673 0.056 Uiso calc R 1 1
C C16 1.04181(18) 0.8345(2) 0.9752(3) 0.0673(8) Uani d . 1 1
H H16A 1.0751 0.8910 0.9303 0.101 Uiso calc R 1 1
H H16B 1.0864 0.7772 1.0264 0.101 Uiso calc R 1 1
H H16C 1.0119 0.8744 1.0414 0.101 Uiso calc R 1 1
C C17 0.58067(14) 0.37547(17) 0.4763(2) 0.0365(5) Uani d . 1 1
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 N1 N2 119.99(16)
C17 N1 C7 127.16(16)
N2 N1 C7 112.76(15)
C9 N2 N1 107.83(16)
C17 N3 H31 120.0
C17 N3 H32 120.0
H31 N3 H32 120.0
C2 C1 F1 118.6(2)
C2 C1 C6 123.1(2)
F1 C1 C6 118.25(19)
C1 C2 C3 118.5(2)
C1 C2 H2 120.7
C3 C2 H2 120.7
C2 C3 C4 120.74(19)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 118.76(18)
C5 C4 C7 120.31(17)
C3 C4 C7 120.86(17)
C4 C5 C6 121.39(19)
C4 C5 H5 119.3
C6 C5 H5 119.3
C1 C6 C5 117.44(19)
C1 C6 H6 121.3
C5 C6 H6 121.3
N1 C7 C4 111.36(16)
N1 C7 C8 100.38(15)
C4 C7 C8 113.31(16)
N1 C7 H7 110.5
C4 C7 H7 110.5
C8 C7 H7 110.5
C9 C8 C7 102.56(16)
C9 C8 H8A 111.3
C7 C8 H8A 111.3
C9 C8 H8B 111.3
C7 C8 H8B 111.3
H8A C8 H8B 109.2
N2 C9 C10 120.57(18)
N2 C9 C8 113.58(17)
C10 C9 C8 125.81(18)
C11 C10 C15 118.05(19)
C11 C10 C9 121.63(19)
C15 C10 C9 120.31(19)
C12 C11 C10 121.0(2)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 121.1(2)
C11 C12 H12 119.4
C13 C12 H12 119.4
C14 C13 C12 117.8(2)
C14 C13 C16 121.6(2)
C12 C13 C16 120.6(2)
C13 C14 C15 121.5(2)
C13 C14 H14 119.3
C15 C14 H14 119.3
C14 C15 C10 120.6(2)
C14 C15 H15 119.7
C10 C15 H15 119.7
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N3 C17 N1 115.16(18)
N3 C17 S1 122.98(16)
N1 C17 S1 121.85(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C17 1.679(2)
F1 C1 1.369(2)
N1 C17 1.349(2)
N1 N2 1.392(2)
N1 C7 1.476(2)
N2 C9 1.288(3)
N3 C17 1.332(2)
N3 H31 0.8800
N3 H32 0.8800
C1 C2 1.361(3)
C1 C6 1.367(3)
C2 C3 1.379(3)
C2 H2 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 C7 1.509(3)
C5 C6 1.389(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.538(3)
C7 H7 0.9800
C8 C9 1.501(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.464(3)
C10 C11 1.383(3)
C10 C15 1.386(3)
C11 C12 1.381(3)
C11 H11 0.9300
C12 C13 1.386(3)
C12 H12 0.9300
C13 C14 1.377(3)
C13 C16 1.505(3)
C14 C15 1.385(3)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
N3 H31 N2 . 0.88 2.23 2.611(3) 106
N3 H31 F1 1_556 0.88 2.41 3.255(2) 162
N3 H32 S1 4_566 0.88 2.83 3.538(2) 138
C16 H16B F1 3_766 0.96 2.55 3.478(3) 163
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
C17 N1 N2 C9 -167.33(17)
C7 N1 N2 C9 9.5(2)
F1 C1 C2 C3 -177.94(19)
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 -1.0(3)
C2 C3 C4 C7 -178.1(2)
C3 C4 C5 C6 1.5(3)
C7 C4 C5 C6 178.58(19)
C2 C1 C6 C5 -0.4(3)
F1 C1 C6 C5 178.42(19)
C4 C5 C6 C1 -0.8(3)
C17 N1 C7 C4 -79.3(2)
N2 N1 C7 C4 104.12(18)
C17 N1 C7 C8 160.42(18)
N2 N1 C7 C8 -16.1(2)
C5 C4 C7 N1 149.56(18)
C3 C4 C7 N1 -33.4(2)
C5 C4 C7 C8 -98.2(2)
C3 C4 C7 C8 78.8(2)
N1 C7 C8 C9 15.56(19)
C4 C7 C8 C9 -103.26(18)
N1 N2 C9 C10 -179.64(16)
N1 N2 C9 C8 2.3(2)
C7 C8 C9 N2 -12.1(2)
C7 C8 C9 C10 169.92(18)
N2 C9 C10 C11 11.6(3)
C8 C9 C10 C11 -170.55(19)
N2 C9 C10 C15 -167.37(19)
C8 C9 C10 C15 10.5(3)
C15 C10 C11 C12 1.4(3)
C9 C10 C11 C12 -177.6(2)
C10 C11 C12 C13 0.9(4)
C11 C12 C13 C14 -2.7(4)
C11 C12 C13 C16 176.3(2)
C12 C13 C14 C15 2.3(3)
C16 C13 C14 C15 -176.7(2)
C13 C14 C15 C10 -0.1(3)
C11 C10 C15 C14 -1.8(3)
C9 C10 C15 C14 177.28(19)
N2 N1 C17 N3 1.2(3)
C7 N1 C17 N3 -175.12(18)
N2 N1 C17 S1 -179.70(14)
C7 N1 C17 S1 4.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24660575
