#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/69/2206972.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_2206972
loop_
_publ_author_name
'Zhong, Ping'
'Zhang, Xiao-Hong'
'Xiao, Hong-Ping'
'Hu, Mao-Lin'
_publ_section_title
5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile
_journal_coeditor_code           HG6237
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3110
_journal_page_last               o3111
_journal_paper_doi               10.1107/S1600536805027054
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H7 Cl4 F3 N4 O'
_chemical_formula_moiety         'C18 H7 Cl4 F3 N4 O'
_chemical_formula_sum            'C18 H7 Cl4 F3 N4 O'
_chemical_formula_weight         494.08
_chemical_melting_point          505
_chemical_name_systematic
;
5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-
1H-pyrazole-3-carbonitrile
;
_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                 99.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7760(11)
_cell_length_b                   16.4530(16)
_cell_length_c                   16.6220(16)
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      2.83
_cell_volume                     2098.6(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10608
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.9037
_exptl_absorpt_correction_T_min  0.8154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.689
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0925
_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)+(0.1073P)²+5.2953P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2336
_refine_ls_wR_factor_ref         0.2440
_reflns_number_gt                3196
_reflns_number_total             3779
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6237.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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               2206972
_cod_database_fobs_code          2206972
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_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_type_symbol
Cl1 0.85543(18) 0.91195(11) 0.22140(10) 0.0767(5) Uani d . 1 Cl
Cl2 0.3192(2) 0.72751(11) 0.27660(11) 0.0820(5) Uani d . 1 Cl
Cl3 0.9410(4) 0.73550(16) 0.05278(14) 0.1392(12) Uani d . 1 Cl
Cl4 0.7241(3) 0.49917(13) -0.15813(9) 0.0939(7) Uani d . 1 Cl
O1 0.9513(6) 0.5777(3) 0.2392(2) 0.0816(14) Uani d . 1 O
F1 0.0914(11) 0.9348(5) 0.0479(6) 0.237(5) Uani d . 1 F
F2 0.1704(16) 1.0236(5) 0.1032(6) 0.261(6) Uani d . 1 F
F3 0.2869(10) 0.9906(9) 0.0181(6) 0.335(9) Uani d . 1 F
N1 0.6910(5) 0.7792(2) 0.3001(2) 0.0449(9) Uani d . 1 N
N2 0.7298(6) 0.8052(3) 0.3781(2) 0.0504(10) Uani d . 1 N
N3 0.9928(7) 0.7688(3) 0.5611(3) 0.0726(15) Uani d . 1 N
N4 0.7663(6) 0.6815(3) 0.2071(2) 0.0544(11) Uani d . 1 N
H4 0.6938 0.7041 0.1691 0.065 Uiso calc R 1 H
C1 0.2354(10) 0.9653(5) 0.0729(5) 0.085(2) Uani d . 1 C
C2 0.3539(7) 0.9168(3) 0.1324(3) 0.0535(13) Uani d . 1 C
C3 0.2871(6) 0.8542(3) 0.1729(3) 0.0527(13) Uani d . 1 C
H3 0.1683 0.8429 0.1631 0.063 Uiso calc R 1 H
C4 0.3983(6) 0.8088(3) 0.2280(3) 0.0469(11) Uani d . 1 C
C5 0.5741(6) 0.8257(3) 0.2430(2) 0.0393(10) Uani d . 1 C
C6 0.6372(6) 0.8890(3) 0.2017(3) 0.0454(11) Uani d . 1 C
C7 0.5268(7) 0.9348(3) 0.1460(3) 0.0516(12) Uani d . 1 C
H7 0.5700 0.9772 0.1182 0.062 Uiso calc R 1 H
C8 0.8497(6) 0.7522(3) 0.4112(3) 0.0454(11) Uani d . 1 C
C9 0.8913(7) 0.6949(3) 0.3565(3) 0.0517(12) Uani d . 1 C
H9 0.9725 0.6531 0.3661 0.062 Uiso calc R 1 H
C10 0.7853(6) 0.7139(3) 0.2845(3) 0.0436(11) Uani d . 1 C
C11 0.9263(7) 0.7620(3) 0.4954(3) 0.0549(13) Uani d . 1 C
C12 0.8574(7) 0.6152(3) 0.1881(3) 0.0531(12) Uani d . 1 C
C13 0.8246(7) 0.5903(3) 0.1004(3) 0.0507(12) Uani d . 1 C
C14 0.8574(8) 0.6381(4) 0.0366(3) 0.0651(15) Uani d . 1 C
C15 0.8280(9) 0.6100(4) -0.0433(3) 0.0728(17) Uani d . 1 C
H15 0.8531 0.6426 -0.0856 0.087 Uiso calc R 1 H
C16 0.7623(7) 0.5346(4) -0.0585(3) 0.0573(14) Uani d . 1 C
C17 0.7324(10) 0.4848(4) 0.0033(4) 0.0770(18) Uani d . 1 C
H17 0.6906 0.4323 -0.0076 0.092 Uiso calc R 1 H
C18 0.7651(10) 0.5136(3) 0.0823(3) 0.0734(18) Uani d . 1 C
H18 0.7458 0.4794 0.1245 0.088 Uiso calc R 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'
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
C10 N1 N2 113.1(4) yes
C10 N1 C5 127.4(4) yes
N2 N1 C5 119.2(4) yes
C8 N2 N1 102.9(4) yes
C12 N4 C10 122.9(4) ?
C12 N4 H4 118.5 ?
C10 N4 H4 118.5 ?
F3 C1 F2 105.4(11) yes
F3 C1 F1 107.4(9) ?
F2 C1 F1 92.5(9) ?
F3 C1 C2 118.4(7) ?
F2 C1 C2 113.7(7) ?
F1 C1 C2 116.1(7) ?
C7 C2 C3 121.6(5) yes
C7 C2 C1 119.2(6) yes
C3 C2 C1 119.2(6) ?
C4 C3 C2 119.1(5) ?
C4 C3 H3 120.5 ?
C2 C3 H3 120.5 ?
C3 C4 C5 120.7(5) yes
C3 C4 Cl2 120.0(4) ?
C5 C4 Cl2 119.3(4) ?
C4 C5 C6 118.9(4) ?
C4 C5 N1 121.3(4) ?
C6 C5 N1 119.7(4) yes
C7 C6 C5 120.9(4) ?
C7 C6 Cl1 119.7(4) ?
C5 C6 Cl1 119.4(3) ?
C2 C7 C6 118.9(5) yes
C2 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
N2 C8 C9 113.4(4) yes
N2 C8 C11 118.8(4) ?
C9 C8 C11 127.8(5) ?
C10 C9 C8 104.2(4) yes
C10 C9 H9 127.9 ?
C8 C9 H9 127.9 ?
N1 C10 C9 106.4(4) ?
N1 C10 N4 120.5(4) yes
C9 C10 N4 133.1(4) yes
N3 C11 C8 177.3(7) ?
O1 C12 N4 121.8(5) yes
O1 C12 C13 122.6(5) ?
N4 C12 C13 115.5(4) yes
C18 C13 C14 117.3(5) yes
C18 C13 C12 117.8(5) ?
C14 C13 C12 124.8(5) ?
C13 C14 C15 121.5(6) ?
C13 C14 Cl3 121.4(4) ?
C15 C14 Cl3 117.1(5) yes
C16 C15 C14 119.0(6) ?
C16 C15 H15 120.5 ?
C14 C15 H15 120.5 ?
C15 C16 C17 121.1(5) ?
C15 C16 Cl4 119.3(5) ?
C17 C16 Cl4 119.6(5) ?
C16 C17 C18 118.9(6) yes
C16 C17 H17 120.6 ?
C18 C17 H17 120.6 ?
C13 C18 C17 122.2(6) yes
C13 C18 H18 118.9 ?
C17 C18 H18 118.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 1.718(5) ?
Cl2 C4 1.726(5) ?
Cl3 C14 1.733(6) ?
Cl4 C16 1.735(5) ?
O1 C12 1.197(6) yes
F1 C1 1.235(10) yes
F2 C1 1.230(11) ?
F3 C1 1.132(9) ?
N1 C10 1.349(6) yes
N1 N2 1.352(5) yes
N1 C5 1.425(5) yes
N2 C8 1.330(6) yes
N3 C11 1.135(6) ?
N4 C12 1.366(6) yes
N4 C10 1.377(6) yes
N4 H4 0.8600 ?
C1 C2 1.473(7) yes
C2 C7 1.359(7) ?
C2 C3 1.377(8) ?
C3 C4 1.375(7) ?
C3 H3 0.9300 ?
C4 C5 1.378(7) ?
C5 C6 1.381(7) yes
C6 C7 1.380(7) ?
C7 H7 0.9300 ?
C8 C9 1.385(7) yes
C8 C11 1.439(6) ?
C9 C10 1.375(6) ?
C9 H9 0.9300 ?
C12 C13 1.496(7) ?
C13 C18 1.361(8) yes
C13 C14 1.377(8) yes
C14 C15 1.390(8) ?
C15 C16 1.350(9) ?
C15 H15 0.9300 ?
C16 C17 1.363(9) ?
C17 C18 1.380(8) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
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
N4 H4 N3 4_575 0.86 2.23 3.068(6) 166
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
C10 N1 N2 C8 -1.4(5) yes
C5 N1 N2 C8 -175.3(4) yes
F3 C1 C2 C7 32.5(15) ?
F2 C1 C2 C7 -92.0(11) ?
F1 C1 C2 C7 162.4(9) yes
F3 C1 C2 C3 -147.4(12) ?
F2 C1 C2 C3 88.2(11) ?
F1 C1 C2 C3 -17.4(12) ?
C7 C2 C3 C4 -0.3(8) yes
C1 C2 C3 C4 179.6(6) ?
C2 C3 C4 C5 0.4(7) ?
C2 C3 C4 Cl2 -177.5(4) ?
C3 C4 C5 C6 -0.2(7) ?
Cl2 C4 C5 C6 177.7(3) ?
C3 C4 C5 N1 179.9(4) yes
Cl2 C4 C5 N1 -2.2(6) ?
C10 N1 C5 C4 93.6(6) ?
N2 N1 C5 C4 -93.5(5) yes
C10 N1 C5 C6 -86.3(6) yes
N2 N1 C5 C6 86.6(5) yes
C4 C5 C6 C7 -0.1(7) ?
N1 C5 C6 C7 179.8(4) yes
C4 C5 C6 Cl1 178.7(4) ?
N1 C5 C6 Cl1 -1.4(6) ?
C3 C2 C7 C6 0.0(8) yes
C1 C2 C7 C6 -179.8(5) ?
C5 C6 C7 C2 0.2(7) ?
Cl1 C6 C7 C2 -178.6(4) ?
N1 N2 C8 C9 1.6(6) ?
N1 N2 C8 C11 178.5(4) ?
N2 C8 C9 C10 -1.2(6) ?
C11 C8 C9 C10 -177.8(5) ?
N2 N1 C10 C9 0.7(6) ?
C5 N1 C10 C9 174.0(5) ?
N2 N1 C10 N4 -177.7(4) yes
C5 N1 C10 N4 -4.4(8) ?
C8 C9 C10 N1 0.3(6) ?
C8 C9 C10 N4 178.4(5) ?
C12 N4 C10 N1 -179.5(5) yes
C12 N4 C10 C9 2.6(9) ?
N2 C8 C11 N3 -143(12) ?
C9 C8 C11 N3 33(13) ?
C10 N4 C12 O1 5.1(9) ?
C10 N4 C12 C13 -177.9(5) ?
O1 C12 C13 C18 55.2(8) ?
N4 C12 C13 C18 -121.8(6) ?
O1 C12 C13 C14 -121.8(7) ?
N4 C12 C13 C14 61.2(7) yes
C18 C13 C14 C15 1.2(9) ?
C12 C13 C14 C15 178.2(6) ?
C18 C13 C14 Cl3 -177.6(5) ?
C12 C13 C14 Cl3 -0.6(8) ?
C13 C14 C15 C16 1.4(10) ?
Cl3 C14 C15 C16 -179.7(5) yes
C14 C15 C16 C17 -3.0(10) ?
C14 C15 C16 Cl4 179.7(5) ?
C15 C16 C17 C18 2.0(10) ?
Cl4 C16 C17 C18 179.3(5) ?
C14 C13 C18 C17 -2.2(10) ?
C12 C13 C18 C17 -179.5(6) ?
C16 C17 C18 C13 0.7(11) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128793
