#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/50/2015015.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_2015015
loop_
_publ_author_name
'Yavuz Köysal'
'Şamil Işık'
'Gülay Şahin'
'Erhan Palaska'
_publ_section_title
;
 Two N-substituted 3,5-diphenyl-2-pyrazoline-1-thiocarboxamides
;
_journal_coeditor_code           GG1282
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o542
_journal_page_last               o544
_journal_paper_doi               10.1107/S0108270105023255
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H18 F N3 S'
_chemical_formula_moiety         'C18 H18 F N3 S'
_chemical_formula_sum            'C18 H18 F N3 S'
_chemical_formula_weight         327.41
_chemical_name_systematic
;
3-(4-fluorophenyl)-N-methyl-5-(4-methylphenyl)-2-pyrazoline-1-thiocarboxamide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.063(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4191(17)
_cell_length_b                   12.2032(11)
_cell_length_c                   14.673(2)
_cell_measurement_reflns_used    11340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      1.42
_cell_volume                     1642.9(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10474
_diffrn_reflns_theta_full        26.63
_diffrn_reflns_theta_max         26.63
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism.
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.463
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.297
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0432
_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)+(0.0738P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                2655
_reflns_number_total             3429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1282.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015015
_cod_database_fobs_code          2015015
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 -0.0791(3) 0.5668(2) 0.32224(18) 0.0780(7) Uani d . 1 . . C
C2 0.0533(2) 0.49507(15) 0.35315(14) 0.0549(5) Uani d . 1 . . C
C3 0.1489(2) 0.51036(15) 0.43928(14) 0.0552(5) Uani d . 1 . . C
C4 0.2688(2) 0.44391(15) 0.46772(12) 0.0510(4) Uani d . 1 . . C
C5 0.29738(19) 0.35865(13) 0.41191(12) 0.0441(4) Uani d . 1 . . C
C6 0.2036(2) 0.34376(15) 0.32543(13) 0.0532(5) Uani d . 1 . . C
C7 0.0841(2) 0.41140(17) 0.29727(14) 0.0583(5) Uani d . 1 . . C
C8 0.4206(2) 0.28008(14) 0.45128(12) 0.0469(4) Uani d . 1 . . C
C9 0.3754(2) 0.20018(15) 0.52082(12) 0.0516(4) Uani d . 1 . . C
C10 0.34190(18) 0.09779(14) 0.46302(11) 0.0446(4) Uani d . 1 . . C
C11 0.26411(18) 0.00248(14) 0.48697(12) 0.0453(4) Uani d . 1 . . C
C12 0.2068(2) 0.00285(16) 0.56652(13) 0.0539(5) Uani d . 1 . . C
C13 0.1255(2) -0.08421(18) 0.58586(14) 0.0612(5) Uani d . 1 . . C
C14 0.1033(2) -0.17167(16) 0.52582(16) 0.0595(5) Uani d . 1 . . C
C15 0.1599(2) -0.17673(17) 0.44849(16) 0.0620(5) Uani d . 1 . . C
C16 0.2407(2) -0.08890(15) 0.42864(14) 0.0537(4) Uani d . 1 . . C
C17 0.52724(19) 0.22231(15) 0.31508(12) 0.0479(4) Uani d . 1 . . C
C18 0.6298(3) 0.13239(19) 0.19464(14) 0.0662(6) Uani d . 1 . . C
N1 0.45171(17) 0.20309(12) 0.38164(10) 0.0494(4) Uani d . 1 . . N
N2 0.38989(16) 0.10033(12) 0.38796(10) 0.0480(4) Uani d . 1 . . N
N3 0.53707(19) 0.13606(13) 0.26064(11) 0.0554(4) Uani d . 1 . . N
F1 0.01935(17) -0.25571(12) 0.54330(11) 0.0881(5) Uani d . 1 . . F
S1 0.60120(6) 0.34546(4) 0.30441(4) 0.0645(2) Uani d . 1 . . S
H1A -0.0840 0.6184 0.3708 0.117 Uiso calc R 1 . . H
H1B -0.1651 0.5220 0.3098 0.117 Uiso calc R 1 . . H
H1C -0.0724 0.6055 0.2664 0.117 Uiso calc R 1 . . H
H3 0.4850 0.0793 0.2652 0.066 Uiso calc R 1 . . H
H3A 0.1315 0.5664 0.4784 0.066 Uiso calc R 1 . . H
H4 0.3319 0.4564 0.5254 0.061 Uiso calc R 1 . . H
H6 0.2212 0.2880 0.2861 0.064 Uiso calc R 1 . . H
H7 0.0225 0.4002 0.2389 0.070 Uiso calc R 1 . . H
H9A 0.4542 0.1884 0.5752 0.062 Uiso calc R 1 . . H
H9B 0.2902 0.2265 0.5410 0.062 Uiso calc R 1 . . H
H12 0.2236 0.0625 0.6070 0.065 Uiso calc R 1 . . H
H13 0.0864 -0.0837 0.6387 0.073 Uiso calc R 1 . . H
H15 0.1447 -0.2380 0.4098 0.074 Uiso calc R 1 . . H
H16 0.2797 -0.0909 0.3758 0.064 Uiso calc R 1 . . H
H18A 0.6190 0.0627 0.1634 0.099 Uiso calc R 1 . . H
H18B 0.7294 0.1421 0.2273 0.099 Uiso calc R 1 . . H
H18C 0.6025 0.1898 0.1494 0.099 Uiso calc R 1 . . H
H18 0.506(2) 0.3208(17) 0.4767(14) 0.059(6) Uiso d . 1 . . H
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
_geom_angle_publ_flag
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C7 C2 C3 117.39(18) ?
C7 C2 C1 121.4(2) ?
C3 C2 C1 121.2(2) ?
C4 C3 C2 121.02(18) ?
C4 C3 H3A 119.5 ?
C2 C3 H3A 119.5 ?
C3 C4 C5 121.20(17) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C4 118.10(17) ?
C6 C5 C8 122.76(15) ?
C4 C5 C8 118.90(15) ?
C7 C6 C5 120.23(18) ?
C7 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C2 C7 C6 122.04(18) ?
C2 C7 H7 119.0 ?
C6 C7 H7 119.0 ?
N1 C8 C5 113.34(14) ?
N1 C8 C9 100.66(14) ?
C5 C8 C9 110.49(15) ?
N1 C8 H18 109.1(13) ?
C5 C8 H18 109.0(13) ?
C9 C8 H18 114.1(13) ?
C10 C9 C8 101.93(14) ?
C10 C9 H9A 111.4 ?
C8 C9 H9A 111.4 ?
C10 C9 H9B 111.4 ?
C8 C9 H9B 111.4 ?
H9A C9 H9B 109.2 ?
N2 C10 C11 121.33(16) ?
N2 C10 C9 113.27(16) ?
C11 C10 C9 125.41(16) ?
C12 C11 C16 118.70(17) ?
C12 C11 C10 120.68(16) ?
C16 C11 C10 120.57(16) ?
C13 C12 C11 120.64(19) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
C14 C13 C12 118.69(19) ?
C14 C13 H13 120.7 ?
C12 C13 H13 120.7 ?
F1 C14 C15 118.66(19) ?
F1 C14 C13 118.61(19) ?
C15 C14 C13 122.72(19) ?
C14 C15 C16 118.6(2) ?
C14 C15 H15 120.7 ?
C16 C15 H15 120.7 ?
C15 C16 C11 120.63(19) ?
C15 C16 H16 119.7 ?
C11 C16 H16 119.7 ?
N3 C17 N1 114.43(16) no
N3 C17 S1 124.25(14) ?
N1 C17 S1 121.31(14) ?
N3 C18 H18A 109.5 ?
N3 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N3 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C17 N1 N2 119.98(14) ?
C17 N1 C8 127.80(15) ?
N2 N1 C8 112.21(14) ?
C10 N2 N1 108.21(14) no
C17 N3 C18 124.00(18) ?
C17 N3 H3 118.0 ?
C18 N3 H3 118.0 ?
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 . 1.507(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.381(3) ?
C2 C3 . 1.388(3) ?
C3 C4 . 1.377(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(2) ?
C5 C8 . 1.516(2) ?
C6 C7 . 1.382(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 N1 . 1.465(2) ?
C8 C9 . 1.540(2) no
C8 H18 . 0.94(2) ?
C9 C10 . 1.503(2) no
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N2 . 1.282(2) no
C10 C11 . 1.459(2) no
C11 C12 . 1.392(3) ?
C11 C16 . 1.393(3) ?
C12 C13 . 1.376(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.370(3) ?
C13 H13 . 0.9300 ?
C14 F1 . 1.355(2) no
C14 C15 . 1.360(3) ?
C15 C16 . 1.383(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 N3 . 1.337(2) ?
C17 N1 . 1.352(2) no
C17 S1 . 1.6786(19) no
C18 N3 . 1.444(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
N1 N2 . 1.395(2) no
N3 H3 . 0.8600 ?
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
N3 H3 N2 0.86 2.20 2.602(2) 108
C6 H6 N1 0.93 2.53 2.866(3) 102
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_publ_flag
C7 C2 C3 C4 -0.4(3) ?
C1 C2 C3 C4 179.27(19) ?
C2 C3 C4 C5 -0.8(3) ?
C3 C4 C5 C6 1.6(3) ?
C3 C4 C5 C8 -172.96(17) ?
C4 C5 C6 C7 -1.1(3) ?
C8 C5 C6 C7 173.21(18) ?
C3 C2 C7 C6 0.9(3) ?
C1 C2 C7 C6 -178.8(2) ?
C5 C6 C7 C2 -0.1(3) ?
C6 C5 C8 N1 13.3(2) ?
C4 C5 C8 N1 -172.38(15) ?
C6 C5 C8 C9 -98.77(19) ?
C4 C5 C8 C9 75.5(2) ?
N1 C8 C9 C10 -17.86(17) ?
C5 C8 C9 C10 102.19(16) ?
C8 C9 C10 N2 14.4(2) ?
C8 C9 C10 C11 -166.06(15) ?
N2 C10 C11 C12 -177.04(16) ?
C9 C10 C11 C12 3.5(3) ?
N2 C10 C11 C16 0.4(3) ?
C9 C10 C11 C16 -179.15(17) ?
C16 C11 C12 C13 -1.6(3) ?
C10 C11 C12 C13 175.83(16) ?
C11 C12 C13 C14 0.6(3) ?
C12 C13 C14 F1 -177.89(18) ?
C12 C13 C14 C15 0.9(3) ?
F1 C14 C15 C16 177.41(18) ?
C13 C14 C15 C16 -1.4(3) ?
C14 C15 C16 C11 0.3(3) ?
C12 C11 C16 C15 1.1(3) ?
C10 C11 C16 C15 -176.32(17) ?
N3 C17 N1 N2 -1.0(2) no
S1 C17 N1 N2 179.15(12) ?
N3 C17 N1 C8 -179.50(16) no
S1 C17 N1 C8 0.7(3) ?
C5 C8 N1 C17 78.5(2) ?
C9 C8 N1 C17 -163.55(17) ?
C5 C8 N1 N2 -100.09(17) ?
C9 C8 N1 N2 17.89(18) ?
C11 C10 N2 N1 176.84(14) ?
C9 C10 N2 N1 -3.6(2) ?
C17 N1 N2 C10 171.44(15) ?
C8 N1 N2 C10 -9.87(19) ?
N1 C17 N3 C18 -170.43(17) ?
S1 C17 N3 C18 9.4(3) ?
