#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/50/2015014.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_2015014
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          'C19 H20 F N3 O S'
_chemical_formula_moiety         'C19 H20 F N3 O S'
_chemical_formula_sum            'C19 H20 F N3 O S'
_chemical_formula_weight         357.44
_chemical_melting_point          412
_chemical_name_systematic
;
N-ethyl-3-(4-fluorophenyl)-5-(4-methoxyphenyl)-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                 120.372(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.706(5)
_cell_length_b                   12.141(5)
_cell_length_c                   17.753(5)
_cell_measurement_reflns_used    46195
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      1.33
_cell_volume                     1804.9(13)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Stoe IPDS-II'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12891
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   '(STOE X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0499P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                2785
_reflns_number_total             3622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1282.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015014
_cod_database_fobs_code          2015014
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 0.9806(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
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'
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
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_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_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
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
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) ?
