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###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2005-07-11
_journal_date_accepted     2005-07-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     o542
_journal_page_last     o544
_journal_paper_category     FO
_journal_coeditor_code     GG1282
_publ_contact_author_name     'Yavuz Köysal'
_publ_contact_author_address
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuz Mayıs University, 55139 Kurupelit
      Samsun, Turkey
;
_publ_contact_author_email     'yavuzk@omu.edu.tr'
_publ_contact_author_fax     ' '
_publ_contact_author_phone     ' '
_publ_section_title
;
Two N-substituted 3,5-diphenyl-2-pyrazoline-1-carboxamides
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yavuz Köysal' ?
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuz Mayıs University, Kurupelit, 55139 Samsun
      Turkey
;
    'Şamil Işık' ?
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuz Mayıs University, Kurupelit, 55139 Samsun
      Turkey
;
    'Gülay Şahin' ?
;     Department of Pharmaceutical Chemistry
      Faculty of Pharmacy
      Hacettepe University, 06100 Sıhhiye, Ankara
      Turkey
;
    'Erhan Palaska' ?
;     Department of Pharmaceutical Chemistry
      Faculty of Pharmacy
      Hacettepe University, 06100 Sıhhiye, Ankara
      Turkey
;
data_I
_chemical_name_systematic
;
N-ethyl-3-(4-fluorophenyl)-5-(4-methoxyphenyl)-2-pyrazoline-1-thiocarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 F N3 O S'
_chemical_formula_sum     'C19 H20 F N3 O S'
_chemical_formula_iupac     'C19 H20 F N3 O S'
_chemical_formula_weight     357.44
_chemical_melting_point     '412'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.706(5)
_cell_length_b     12.141(5)
_cell_length_c     17.753(5)
_cell_angle_alpha     90.00
_cell_angle_beta     120.372(17)
_cell_angle_gamma     90.00
_cell_volume     1804.9(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     46195
_cell_measurement_theta_min     1.33
_cell_measurement_theta_max     26.66
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.54
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.315
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.201
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     '(STOE X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS-II'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     12891
_diffrn_reflns_av_R_equivalents     0.0429
_diffrn_reflns_av_sigmaI/netI     0.0324
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     26.31
_diffrn_reflns_theta_full     26.31
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3622
_reflns_number_gt     2785
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0474
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0867
_refine_ls_wR_factor_ref     0.0915
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.035
_refine_ls_number_reflns     3622
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0499P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.141
_refine_diff_density_min     -0.152
_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'
    '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     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
                             'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
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 0.9806(3) 0.72994(18) 0.20341(14) 0.0839(6) Uani d . 1 . . C
    C2 0.91737(15) 0.86849(11) 0.27695(9) 0.0455(3) Uani d . 1 . . C
    C3 0.97484(15) 0.93586(12) 0.34925(9) 0.0489(3) Uani d . 1 . . C
    C4 0.87103(15) 0.99298(11) 0.36604(9) 0.0457(3) Uani d . 1 . . C
    C5 0.70652(15) 0.98556(10) 0.31049(9) 0.0430(3) Uani d . 1 . . C
    C6 0.65160(16) 0.91931(12) 0.23769(9) 0.0513(3) Uani d . 1 . . C
    C7 0.75442(16) 0.86029(13) 0.22029(9) 0.0524(4) Uani d . 1 . . C
    C8 0.59425(16) 1.04925(12) 0.32998(10) 0.0484(3) Uani d . 1 . . C
    C9 0.47674(17) 1.12380(12) 0.25474(12) 0.0581(4) Uani d . 1 . . C
    C10 0.31872(16) 1.06658(11) 0.22181(9) 0.0453(3) Uani d . 1 . . C
    C11 0.16867(16) 1.09685(11) 0.14357(9) 0.0457(3) Uani d . 1 . . C
    C12 0.16151(19) 1.18543(12) 0.09248(10) 0.0534(4) Uani d . 1 . . C
    C13 0.0200(2) 1.21216(13) 0.01723(10) 0.0604(4) Uani d . 1 . . C
    C14 -0.11108(19) 1.14910(14) -0.00541(10) 0.0586(4) Uani d . 1 . . C
    C15 -0.11049(18) 1.06157(14) 0.04359(11) 0.0597(4) Uani d . 1 . . C
    C16 0.03008(17) 1.03551(13) 0.11859(10) 0.0525(3) Uani d . 1 . . C
    C17 0.51387(15) 0.90727(11) 0.40617(9) 0.0435(3) Uani d . 1 . . C
    C18 0.39898(19) 0.77132(14) 0.46138(11) 0.0600(4) Uani d . 1 . . C
    C19 0.4651(2) 0.65993(15) 0.46169(14) 0.0757(5) Uani d . 1 . . C
    N1 0.48105(12) 0.97533(10) 0.33845(8) 0.0491(3) Uani d . 1 . . N
    N2 0.32498(12) 0.98592(10) 0.26989(7) 0.0468(3) Uani d . 1 . . N
    N3 0.39258(14) 0.84378(11) 0.39485(8) 0.0510(3) Uani d . 1 . . N
    O1 1.03063(12) 0.81323(10) 0.26744(8) 0.0635(3) Uani d . 1 . . O
    F1 -0.24975(12) 1.17383(10) -0.08014(6) 0.0842(3) Uani d . 1 . . F
    S1 0.69494(4) 0.90641(4) 0.49604(2) 0.05958(14) Uani d . 1 . . S
    H1A 0.9259 0.6733 0.2158 0.126 Uiso calc R 1 . . H
    H1B 1.0720 0.6990 0.2039 0.126 Uiso calc R 1 . . H
    H1C 0.9098 0.7609 0.1470 0.126 Uiso calc R 1 . . H
    H3 1.0844 0.9427 0.3868 0.059 Uiso calc R 1 . . H
    H4 0.9114 1.0374 0.4154 0.055 Uiso calc R 1 . . H
    H6 0.7144 0.8157 0.1711 0.063 Uiso calc R 1 . . H
    H7 0.5422 0.9142 0.1991 0.062 Uiso calc R 1 . . H
    H8 0.6546(18) 1.0908(13) 0.3862(10) 0.055(4) Uiso d . 1 . . H
    H9A 0.4748 1.1974 0.2755 0.070 Uiso calc R 1 . . H
    H9B 0.5045 1.1286 0.2095 0.070 Uiso calc R 1 . . H
    H12 0.2526 1.2274 0.1088 0.064 Uiso calc R 1 . . H
    H13 0.0148 1.2718 -0.0170 0.072 Uiso calc R 1 . . H
    H15 -0.2028 1.0208 0.0266 0.072 Uiso calc R 1 . . H
    H16 0.0329 0.9767 0.1529 0.063 Uiso calc R 1 . . H
    H18A 0.2921 0.7628 0.4521 0.072 Uiso calc R 1 . . H
    H18B 0.4645 0.8052 0.5181 0.072 Uiso calc R 1 . . H
    H19A 0.5718 0.6675 0.4722 0.113 Uiso calc R 1 . . H
    H19B 0.3993 0.6251 0.4062 0.113 Uiso calc R 1 . . H
    H19C 0.4665 0.6157 0.5069 0.113 Uiso calc R 1 . . H
    H20 0.301(2) 0.8533(15) 0.3479(12) 0.066(5) Uiso d . 1 . . H
_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 O1 . 1.411(2) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 O1 . 1.3692(17) ?
    C2 C3 . 1.380(2) ?
    C2 C7 . 1.384(2) ?
    C3 C4 . 1.374(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.3921(19) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.380(2) ?
    C5 C8 . 1.512(2) ?
    C6 C7 . 1.384(2) ?
    C6 H7 . 0.9300 ?
    C7 H6 . 0.9300 ?
    C8 N1 . 1.4840(18) ?
    C8 C9 . 1.537(2) no
    C8 H8 . 1.001(16) ?
    C9 C10 . 1.507(2) no
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N2 . 1.2802(18) no
    C10 C11 . 1.4627(19) ?
    C11 C12 . 1.386(2) ?
    C11 C16 . 1.399(2) ?
    C12 C13 . 1.386(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.360(3) ?
    C13 H13 . 0.9300 ?
    C14 F1 . 1.3624(18) no
    C14 C15 . 1.372(2) ?
    C15 C16 . 1.377(2) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 N3 . 1.3345(18) ?
    C17 N1 . 1.3574(18) no
    C17 S1 . 1.6729(15) no
    C18 N3 . 1.449(2) ?
    C18 C19 . 1.496(2) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    N1 N2 . 1.3886(16) no
    N3 H20 . 0.865(18) ?
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
    O1 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    O1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C3 . . 115.66(12) ?
    O1 C2 C7 . . 124.68(13) ?
    C3 C2 C7 . . 119.66(13) ?
    C4 C3 C2 . . 120.33(12) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.8 ?
    C3 C4 C5 . . 121.19(13) ?
    C3 C4 H4 . . 119.4 ?
    C5 C4 H4 . . 119.4 ?
    C6 C5 C4 . . 117.56(12) ?
    C6 C5 C8 . . 122.04(12) ?
    C4 C5 C8 . . 120.40(13) ?
    C5 C6 C7 . . 122.00(12) ?
    C5 C6 H7 . . 119.0 ?
    C7 C6 H7 . . 119.0 ?
    C6 C7 C2 . . 119.24(13) ?
    C6 C7 H6 . . 120.4 ?
    C2 C7 H6 . . 120.4 ?
    N1 C8 C5 . . 111.72(12) ?
    N1 C8 C9 . . 100.49(11) ?
    C5 C8 C9 . . 113.96(13) ?
    N1 C8 H8 . . 107.1(9) ?
    C5 C8 H8 . . 111.0(9) ?
    C9 C8 H8 . . 111.9(9) ?
    C10 C9 C8 . . 103.19(12) ?
    C10 C9 H9A . . 111.1 ?
    C8 C9 H9A . . 111.1 ?
    C10 C9 H9B . . 111.1 ?
    C8 C9 H9B . . 111.1 ?
    H9A C9 H9B . . 109.1 ?
    N2 C10 C11 . . 120.94(12) ?
    N2 C10 C9 . . 113.46(13) ?
    C11 C10 C9 . . 125.60(13) ?
    C12 C11 C16 . . 118.92(14) ?
    C12 C11 C10 . . 120.85(13) ?
    C16 C11 C10 . . 120.22(13) ?
    C11 C12 C13 . . 120.65(15) ?
    C11 C12 H12 . . 119.7 ?
    C13 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 118.45(15) ?
    C14 C13 H13 . . 120.8 ?
    C12 C13 H13 . . 120.8 ?
    C13 C14 F1 . . 118.67(15) ?
    C13 C14 C15 . . 123.06(14) ?
    F1 C14 C15 . . 118.27(16) ?
    C14 C15 C16 . . 118.39(15) ?
    C14 C15 H15 . . 120.8 ?
    C16 C15 H15 . . 120.8 ?
    C15 C16 C11 . . 120.52(15) ?
    C15 C16 H16 . . 119.7 ?
    C11 C16 H16 . . 119.7 ?
    N3 C17 N1 . . 115.09(12) no
    N3 C17 S1 . . 124.15(11) ?
    N1 C17 S1 . . 120.76(10) ?
    N3 C18 C19 . . 113.17(14) ?
    N3 C18 H18A . . 108.9 ?
    C19 C18 H18A . . 108.9 ?
    N3 C18 H18B . . 108.9 ?
    C19 C18 H18B . . 108.9 ?
    H18A C18 H18B . . 107.8 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C17 N1 N2 . . 119.75(11) ?
    C17 N1 C8 . . 127.13(11) ?
    N2 N1 C8 . . 113.00(11) ?
    C10 N2 N1 . . 108.55(11) no
    C17 N3 C18 . . 123.85(13) ?
    C17 N3 H20 . . 117.7(12) ?
    C18 N3 H20 . . 117.9(12) ?
    C2 O1 C1 . . 118.65(12) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C2 C3 C4 . . . . -178.43(13) ?
    C7 C2 C3 C4 . . . . 1.3(2) ?
    C2 C3 C4 C5 . . . . -0.8(2) ?
    C3 C4 C5 C6 . . . . -0.4(2) ?
    C3 C4 C5 C8 . . . . -179.86(13) ?
    C4 C5 C6 C7 . . . . 1.1(2) ?
    C8 C5 C6 C7 . . . . -179.44(14) ?
    C5 C6 C7 C2 . . . . -0.6(2) ?
    O1 C2 C7 C6 . . . . 179.09(14) ?
    C3 C2 C7 C6 . . . . -0.6(2) ?
    C6 C5 C8 N1 . . . . 58.71(17) ?
    C4 C5 C8 N1 . . . . -121.86(13) ?
    C6 C5 C8 C9 . . . . -54.33(18) ?
    C4 C5 C8 C9 . . . . 125.10(14) ?
    N1 C8 C9 C10 . . . . -10.40(15) ?
    C5 C8 C9 C10 . . . . 109.21(13) ?
    C8 C9 C10 N2 . . . . 7.85(17) ?
    C8 C9 C10 C11 . . . . -172.63(13) ?
    N2 C10 C11 C12 . . . . 178.83(14) ?
    C9 C10 C11 C12 . . . . -0.7(2) ?
    N2 C10 C11 C16 . . . . -2.0(2) ?
    C9 C10 C11 C16 . . . . 178.53(14) ?
    C16 C11 C12 C13 . . . . -0.8(2) ?
    C10 C11 C12 C13 . . . . 178.41(13) ?
    C11 C12 C13 C14 . . . . -0.4(2) ?
    C12 C13 C14 F1 . . . . -178.84(13) ?
    C12 C13 C14 C15 . . . . 1.3(2) ?
    C13 C14 C15 C16 . . . . -0.9(2) ?
    F1 C14 C15 C16 . . . . 179.18(13) ?
    C14 C15 C16 C11 . . . . -0.3(2) ?
    C12 C11 C16 C15 . . . . 1.1(2) ?
    C10 C11 C16 C15 . . . . -178.07(13) ?
    N3 C17 N1 N2 . . . . 8.69(18) no
    S1 C17 N1 N2 . . . . -171.12(10) ?
    N3 C17 N1 C8 . . . . -175.64(13) no
    S1 C17 N1 C8 . . . . 4.55(19) ?
    C5 C8 N1 C17 . . . . 73.89(18) ?
    C9 C8 N1 C17 . . . . -164.89(14) ?
    C5 C8 N1 N2 . . . . -110.20(13) ?
    C9 C8 N1 N2 . . . . 11.02(15) ?
    C11 C10 N2 N1 . . . . 179.40(12) ?
    C9 C10 N2 N1 . . . . -1.05(17) ?
    C17 N1 N2 C10 . . . . 169.43(12) ?
    C8 N1 N2 C10 . . . . -6.82(16) ?
    N1 C17 N3 C18 . . . . -175.43(13) ?
    S1 C17 N3 C18 . . . . 4.4(2) ?
    C19 C18 N3 C17 . . . . -86.88(19) ?
    C3 C2 O1 C1 . . . . 169.97(16) ?
    C7 C2 O1 C1 . . . . -9.7(2) ?
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 H20 O1 1_455 0.865(18) 2.319(18) 3.092(2) 148.9(15)
    N3 H20 N2 . 0.865(18) 2.211(17) 2.6187(18) 108.7(14)
    C3 H3 S1 3_776 0.93 2.79 3.5471(18) 140
    C18 H18B S1 . 0.97 2.75 3.088(2) 101
data_II
_chemical_name_systematic
;
3-(4-fluorophenyl)-N-methyl-5-(4-methylphenyl)-2-pyrazoline-1-thiocarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H18 F N3 S'
_chemical_formula_sum     'C18 H18 F N3 S'
_chemical_formula_iupac     'C18 H18 F N3 S'
_chemical_formula_weight     327.41
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.4191(17)
_cell_length_b     12.2032(11)
_cell_length_c     14.673(2)
_cell_angle_alpha     90.00
_cell_angle_beta     103.063(14)
_cell_angle_gamma     90.00
_cell_volume     1642.9(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     11340
_cell_measurement_theta_min     1.42
_cell_measurement_theta_max     26.66
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism.'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.600
_exptl_crystal_size_mid     0.463
_exptl_crystal_size_min     0.250
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.210
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.885
_exptl_absorpt_correction_T_max     0.954
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS 2'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     10474
_diffrn_reflns_av_R_equivalents     0.0510
_diffrn_reflns_av_sigmaI/netI     0.0343
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     26.63
_diffrn_reflns_theta_full     26.63
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3429
_reflns_number_gt     2655
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0562
_refine_ls_R_factor_gt     0.0432
_refine_ls_wR_factor_gt     0.1222
_refine_ls_wR_factor_ref     0.1397
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     3429
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0738P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.234
_refine_diff_density_min     -0.297
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.041(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
                             'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
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
_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 . 1.507(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_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 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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_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) ?
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 H3 N2 . 0.86 2.20 2.602(2) 108
    C6 H6 N1 . 0.93 2.53 2.866(3) 102
