#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/31/8103156.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_8103156
loop_
_publ_author_name
'Jun Dai'
'Xiao-Hong Zhang'
'Chenghai Wu'
'Mingmin Wang'
'Ping Zhong'
_publ_section_title
;
 Crystal structure of N-[1-(2,6-dichloro-4-trifluoro-
 methyl)-phenyl-3-cyano-1H-pyrazol-5-yl]-N'-4-chlorobenzoyl-thiourea,
 C19H9Cl3F3N5OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              307
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C19 H9 Cl3 F3 N5 O S'
_chemical_formula_sum            'C19 H9 Cl3 F3 N5 O S'
_chemical_formula_weight         518.72
_chemical_melting_point          482.5(5)
_chemical_name_systematic
;
N-[1-(2,6-dichloro-4-trifluoromethyl)
phenyl-3-cyano-1H-pyrazol-5-yl]-N'-4-chlorobenzoyl Thioureas
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.280(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9725(16)
_cell_length_b                   7.3779(7)
_cell_length_c                   17.3459(17)
_cell_measurement_reflns_used    4074
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.40
_cell_volume                     2166.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10964
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  0.8757
_exptl_absorpt_correction_T_min  0.8304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0736
_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)+(0.0673P)²+3.7649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                3387
_reflns_number_total             3810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-3421.cff
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '482-483' was changed to '482.5(5)' -
the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8103156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.76040(6) 0.5722(2) 0.15844(7) 0.0568(4) Uani 1 1 d .
O1 O 1.01410(17) 0.7530(5) 0.15196(17) 0.0566(9) Uani 1 1 d .
F1 F 1.2254(3) 1.1789(9) 0.3240(6) 0.245(5) Uani 1 1 d .
F2 F 1.2817(2) 0.9446(7) 0.3424(4) 0.161(3) Uani 1 1 d .
F3 F 1.2521(4) 1.0868(15) 0.4293(5) 0.264(6) Uani 1 1 d .
N1 N 0.88963(19) 0.6918(5) 0.10182(19) 0.0416(8) Uani 1 1 d .
H1 H 0.8603 0.6914 0.0592 0.050 Uiso 1 1 calc R
N2 N 0.8958(2) 0.6797(5) 0.23412(19) 0.0440(8) Uani 1 1 d .
H2 H 0.9411 0.7291 0.2298 0.053 Uiso 1 1 calc R
N3 N 0.92881(19) 0.6895(5) 0.36841(19) 0.0445(9) Uani 1 1 d .
N4 N 0.9045(2) 0.6374(5) 0.4380(2) 0.0490(9) Uani 1 1 d .
N5 N 0.7537(3) 0.4135(7) 0.5217(3) 0.0765(14) Uani 1 1 d .
C1 C 1.0499(3) 0.7993(6) -0.1276(2) 0.0452(10) Uani 1 1 d .
C2 C 1.1027(3) 0.7774(7) -0.0639(3) 0.0510(11) Uani 1 1 d .
H2A H 1.1568 0.7770 -0.0690 0.061 Uiso 1 1 calc R
C3 C 1.0735(2) 0.7563(6) 0.0073(3) 0.0483(10) Uani 1 1 d .
H3 H 1.1085 0.7436 0.0509 0.058 Uiso 1 1 calc R
C4 C 0.9930(2) 0.7534(5) 0.0155(2) 0.0372(9) Uani 1 1 d .
C5 C 0.9416(2) 0.7752(6) -0.0494(2) 0.0481(11) Uani 1 1 d .
H5 H 0.8873 0.7737 -0.0447 0.058 Uiso 1 1 calc R
C6 C 0.9698(3) 0.7991(7) -0.1209(3) 0.0560(12) Uani 1 1 d .
H6 H 0.9350 0.8150 -0.1644 0.067 Uiso 1 1 calc R
C7 C 0.9676(2) 0.7335(5) 0.0954(2) 0.0399(9) Uani 1 1 d .
C8 C 0.8513(2) 0.6498(5) 0.1681(2) 0.0380(9) Uani 1 1 d .
C9 C 0.8767(2) 0.6398(6) 0.3084(2) 0.0412(9) Uani 1 1 d .
C10 C 0.8152(3) 0.5529(6) 0.3393(3) 0.0475(11) Uani 1 1 d .
H10 H 0.7701 0.5039 0.3135 0.057 Uiso 1 1 calc R
C11 C 0.8361(2) 0.5550(6) 0.4188(2) 0.0463(10) Uani 1 1 d .
C12 C 0.7918(3) 0.4768(7) 0.4778(3) 0.0555(12) Uani 1 1 d .
C13 C 1.0026(2) 0.7800(6) 0.3654(2) 0.0389(9) Uani 1 1 d .
C14 C 1.0675(2) 0.6890(6) 0.3401(3) 0.0461(10) Uani 1 1 d .
C15 C 1.1398(3) 0.7738(7) 0.3375(3) 0.0530(12) Uani 1 1 d .
H15 H 1.1825 0.7134 0.3189 0.064 Uiso 1 1 calc R
C16 C 1.1469(2) 0.9499(7) 0.3632(3) 0.0520(12) Uani 1 1 d .
C17 C 1.0838(2) 1.0429(6) 0.3891(2) 0.0454(10) Uani 1 1 d .
H17 H 1.0899 1.1616 0.4066 0.054 Uiso 1 1 calc R
C18 C 1.0116(2) 0.9583(6) 0.3887(2) 0.0398(9) Uani 1 1 d .
C19 C 1.2252(3) 1.0430(10) 0.3624(5) 0.0839(19) Uani 1 1 d .
Cl1 Cl 1.08635(8) 0.83380(19) -0.21759(7) 0.0652(4) Uani 1 1 d .
Cl2 Cl 1.05809(9) 0.46684(18) 0.31074(10) 0.0748(4) Uani 1 1 d .
Cl3 Cl 0.93154(7) 1.07746(18) 0.41736(7) 0.0568(3) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C8 128.9(3) yes
C7 N1 H1 115.5 ?
C8 N1 H1 115.5 ?
C8 N2 C9 127.1(3) yes
C8 N2 H2 116.4 ?
C9 N2 H2 116.4 ?
N4 N3 C9 112.3(3) yes
N4 N3 C13 119.4(3) yes
C9 N3 C13 128.3(3) yes
C11 N4 N3 103.0(3) yes
C6 C1 C2 121.4(4) ?
C6 C1 Cl1 119.7(4) ?
C2 C1 Cl1 118.9(3) ?
C3 C2 C1 118.5(4) yes
C3 C2 H2A 120.7 ?
C1 C2 H2A 120.7 ?
C2 C3 C4 121.2(4) ?
C2 C3 H3 119.4 ?
C4 C3 H3 119.4 ?
C5 C4 C3 118.9(4) yes
C5 C4 C7 124.1(4) ?
C3 C4 C7 117.0(4) yes
C6 C5 C4 120.5(4) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C1 C6 C5 119.4(4) ?
C1 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
O1 C7 N1 122.1(4) yes
O1 C7 C4 121.4(4) ?
N1 C7 C4 116.5(4) ?
N2 C8 N1 113.5(3) yes
N2 C8 S1 127.5(3) ?
N1 C8 S1 119.0(3) yes
N3 C9 C10 107.2(4) ?
N3 C9 N2 118.1(3) yes
C10 C9 N2 134.7(4) ?
C9 C10 C11 103.7(4) ?
C9 C10 H10 128.1 ?
C11 C10 H10 128.1 ?
N4 C11 C10 113.8(4) yes
N4 C11 C12 120.0(4) ?
C10 C11 C12 126.2(4) ?
N5 C12 C11 176.6(5) ?
C18 C13 C14 118.7(4) ?
C18 C13 N3 120.9(4) ?
C14 C13 N3 120.4(4) ?
C15 C14 C13 121.2(4) ?
C15 C14 Cl2 119.0(4) ?
C13 C14 Cl2 119.7(3) ?
C16 C15 C14 118.4(4) ?
C16 C15 H15 120.8 ?
C14 C15 H15 120.8 ?
C17 C16 C15 121.6(4) ?
C17 C16 C19 119.2(5) yes
C15 C16 C19 119.2(5) ?
C18 C17 C16 119.2(4) ?
C18 C17 H17 120.4 ?
C16 C17 H17 120.4 ?
C17 C18 C13 120.8(4) ?
C17 C18 Cl3 119.3(3) ?
C13 C18 Cl3 119.9(3) ?
F1 C19 F3 106.3(8) ?
F1 C19 F2 106.9(7) ?
F3 C19 F2 99.7(7) ?
F1 C19 C16 115.3(6) ?
F3 C19 C16 111.8(6) ?
F2 C19 C16 115.4(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.642(4) ?
O1 C7 1.221(5) yes
F1 C19 1.204(8) ?
F2 C19 1.272(8) ?
F3 C19 1.258(9) ?
N1 C7 1.371(5) yes
N1 C8 1.397(5) yes
N1 H1 0.8600 ?
N2 C8 1.343(5) yes
N2 C9 1.383(5) yes
N2 H2 0.8600 ?
N3 N4 1.359(5) yes
N3 C9 1.365(5) yes
N3 C13 1.424(5) ?
N4 C11 1.331(5) yes
N5 C12 1.136(6) ?
C1 C6 1.372(6) yes
C1 C2 1.379(6) ?
C1 Cl1 1.741(4) ?
C2 C3 1.373(6) ?
C2 H2A 0.9300 ?
C3 C4 1.384(6) yes
C3 H3 0.9300 ?
C4 C5 1.382(6) ?
C4 C7 1.490(6) ?
C5 C6 1.374(6) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C9 C10 1.369(6) ?
C10 C11 1.398(6) ?
C10 H10 0.9300 ?
C11 C12 1.435(6) ?
C13 C18 1.381(6) ?
C13 C14 1.389(6) ?
C14 C15 1.380(6) yes
C14 Cl2 1.720(5) ?
C15 C16 1.376(7) ?
C15 H15 0.9300 ?
C16 C17 1.376(6) ?
C16 C19 1.496(7) yes
C17 C18 1.375(6) ?
C17 H17 0.9300 ?
C18 Cl3 1.722(4) ?
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
N2 H2 O1 0.86 1.91 2.604(4) 137.2
