#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208030.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_2208030
loop_
_publ_author_name
'Zhong, Ping'
'Zhang, Xiao-Hong'
'Xiao, Hong-Ping'
'Hu, Mao-Lin'
_publ_section_title
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(4-methylphenylsulfonamido)-1H-pyrazole-3-carbonitrile
_journal_coeditor_code           CV6627
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o513
_journal_page_last               o515
_journal_paper_doi               10.1107/S1600536806000250
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H11 Cl2 F3 N4 O2 S'
_chemical_formula_moiety         'C18 H11 Cl2 F3 N4 O2 S'
_chemical_formula_sum            'C18 H11 Cl2 F3 N4 O2 S'
_chemical_formula_weight         475.27
_chemical_melting_point          500
_chemical_name_systematic
;
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(4-methylphenylsulfonamido)-
1H-pyrazole-3-carbonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.699(2)
_cell_angle_beta                 102.171(2)
_cell_angle_gamma                102.984(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4636(10)
_cell_length_b                   10.0256(11)
_cell_length_c                   11.6641(13)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.68
_cell_volume                     1011.81(19)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5392
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.8947
_exptl_absorpt_correction_T_min  0.8220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.568
_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     272
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0671
_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)+(0.1091P)²+0.809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.1994
_reflns_number_gt                3041
_reflns_number_total             3585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6627.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2208030
_cod_database_fobs_code          2208030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.24676(13) 0.17381(12) 0.04594(11) 0.0849(4) Uani d . 1 Cl
Cl2 0.26409(12) 0.58352(13) 0.43682(10) 0.0850(4) Uani d . 1 Cl
S1 0.22246(10) 0.67516(12) 0.02203(9) 0.0674(3) Uani d . 1 S
F1 -0.2526(5) 0.0490(7) 0.1945(5) 0.217(3) Uani d . 1 F
F2 -0.1274(7) -0.0073(8) 0.3135(11) 0.332(7) Uani d . 1 F
F3 -0.2027(5) 0.1568(5) 0.3686(5) 0.197(3) Uani d . 1 F
O1 0.0660(3) 0.6365(3) -0.0435(3) 0.0845(9) Uani d . 1 O
O2 0.3358(3) 0.7113(4) -0.0377(3) 0.0827(9) Uani d . 1 O
N1 0.3702(3) 0.4570(3) 0.2252(3) 0.0542(7) Uani d . 1 N
N2 0.5109(3) 0.4639(3) 0.2888(3) 0.0621(8) Uani d . 1 N
N3 0.8869(4) 0.6156(5) 0.3302(4) 0.0996(14) Uani d . 1 N
N4 0.2390(3) 0.5341(3) 0.0669(3) 0.0634(8) Uani d . 1 N
H4 0.1629 0.4593 0.0428 0.076 Uiso calc R 1 H
C1 -0.1453(6) 0.1022(6) 0.2902(5) 0.0897(14) Uani d . 1 C
C2 -0.0084(4) 0.1947(5) 0.2745(4) 0.0677(10) Uani d . 1 C
C3 0.0500(4) 0.1434(4) 0.1810(4) 0.0677(10) Uani d . 1 C
H3 0.0063 0.0513 0.1294 0.081 Uiso calc R 1 H
C4 0.1746(4) 0.2316(4) 0.1658(3) 0.0592(8) Uani d . 1 C
C5 0.2414(3) 0.3674(4) 0.2437(3) 0.0536(8) Uani d . 1 C
C6 0.1816(4) 0.4155(4) 0.3379(3) 0.0597(9) Uani d . 1 C
C7 0.0557(4) 0.3294(5) 0.3541(4) 0.0667(10) Uani d . 1 C
H7 0.0152 0.3615 0.4174 0.080 Uiso calc R 1 H
C8 0.5988(4) 0.5499(4) 0.2458(3) 0.0583(8) Uani d . 1 C
C9 0.5204(4) 0.5955(4) 0.1535(3) 0.0605(9) Uani d . 1 C
H9 0.5595 0.6548 0.1097 0.073 Uiso calc R 1 H
C10 0.3725(3) 0.5322(4) 0.1427(3) 0.0525(8) Uani d . 1 C
C11 0.7595(4) 0.5842(5) 0.2933(4) 0.0741(11) Uani d . 1 C
C12 0.2590(4) 0.8121(4) 0.1560(4) 0.0646(10) Uani d . 1 C
C13 0.1649(5) 0.8001(5) 0.2315(5) 0.0772(12) Uani d . 1 C
H13 0.0818 0.7205 0.2101 0.093 Uiso calc R 1 H
C14 0.1939(5) 0.9049(5) 0.3373(5) 0.0839(13) Uani d . 1 C
H14 0.1307 0.8954 0.3880 0.101 Uiso calc R 1 H
C15 0.3170(5) 1.0266(5) 0.3708(5) 0.0802(12) Uani d . 1 C
C16 0.4079(5) 1.0364(5) 0.2941(6) 0.0904(14) Uani d . 1 C
H16 0.4899 1.1168 0.3145 0.109 Uiso calc R 1 H
C17 0.3815(4) 0.9306(5) 0.1874(5) 0.0809(12) Uani d . 1 C
H17 0.4456 0.9392 0.1374 0.097 Uiso calc R 1 H
C18 0.3459(7) 1.1412(6) 0.4869(6) 0.1056(16) Uani d . 1 C
H18A 0.4334 1.1399 0.5454 0.158 Uiso calc R 1 H
H18B 0.2602 1.1246 0.5190 0.158 Uiso calc R 1 H
H18C 0.3627 1.2324 0.4705 0.158 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'
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
O2 S1 O1 120.19(18) yes
O2 S1 N4 108.35(18) yes
O1 S1 N4 103.39(16) ?
O2 S1 C12 108.68(19) yes
O1 S1 C12 109.63(19) ?
N4 S1 C12 105.57(17) yes
C10 N1 N2 112.5(3) yes
C10 N1 C5 127.6(3) yes
N2 N1 C5 119.8(3) ?
C8 N2 N1 103.0(3) ?
C10 N4 S1 121.8(2) ?
C10 N4 H4 119.1 yes
S1 N4 H4 119.1 ?
F2 C1 F3 105.7(6) yes
F2 C1 F1 99.7(7) ?
F3 C1 F1 104.5(5) ?
F2 C1 C2 113.7(5) ?
F3 C1 C2 117.1(5) ?
F1 C1 C2 114.3(5) ?
C3 C2 C7 122.2(3) ?
C3 C2 C1 119.1(4) ?
C7 C2 C1 118.7(4) ?
C4 C3 C2 118.4(4) ?
C4 C3 H3 120.8 ?
C2 C3 H3 120.8 ?
C3 C4 C5 120.9(4) ?
C3 C4 Cl1 119.8(3) ?
C5 C4 Cl1 119.2(3) ?
C4 C5 C6 119.5(3) yes
C4 C5 N1 119.7(3) ?
C6 C5 N1 120.8(3) ?
C7 C6 C5 120.6(4) ?
C7 C6 Cl2 119.2(3) ?
C5 C6 Cl2 120.2(3) ?
C2 C7 C6 118.4(4) ?
C2 C7 H7 120.8 ?
C6 C7 H7 120.8 ?
N2 C8 C9 113.8(3) yes
N2 C8 C11 119.2(3) ?
C9 C8 C11 127.0(3) ?
C10 C9 C8 103.5(3) ?
C10 C9 H9 128.2 ?
C8 C9 H9 128.2 ?
N1 C10 C9 107.2(3) ?
N1 C10 N4 120.6(3) ?
C9 C10 N4 132.3(3) ?
N3 C11 C8 177.8(5) ?
C17 C12 C13 119.9(5) ?
C17 C12 S1 120.6(3) ?
C13 C12 S1 119.5(3) ?
C14 C13 C12 120.1(4) ?
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 121.1(4) ?
C13 C14 H14 119.5 ?
C15 C14 H14 119.5 ?
C16 C15 C14 117.7(5) ?
C16 C15 C18 122.0(5) ?
C14 C15 C18 120.2(5) yes
C15 C16 C17 122.0(4) ?
C15 C16 H16 119.0 ?
C17 C16 H16 119.0 ?
C12 C17 C16 119.3(4) ?
C12 C17 H17 120.4 ?
C16 C17 H17 120.4 ?
C15 C18 H18A 109.5 ?
C15 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C15 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.727(4) ?
Cl2 C6 1.718(4) ?
S1 O2 1.421(3) yes
S1 O1 1.436(3) ?
S1 N4 1.640(3) yes
S1 C12 1.749(5) ?
F1 C1 1.256(7) yes
F2 C1 1.226(7) ?
F3 C1 1.246(6) ?
N1 C10 1.348(4) yes
N1 N2 1.359(4) yes
N1 C5 1.430(4) yes
N2 C8 1.315(5) ?
N3 C11 1.135(5) ?
N4 C10 1.387(4) yes
N4 H4 0.8600 ?
C1 C2 1.485(5) yes
C2 C3 1.376(6) ?
C2 C7 1.377(6) ?
C3 C4 1.376(5) ?
C3 H3 0.9300 ?
C4 C5 1.381(5) yes
C5 C6 1.383(5) ?
C6 C7 1.381(5) ?
C7 H7 0.9300 ?
C8 C9 1.397(5) ?
C8 C11 1.437(5) ?
C9 C10 1.367(4) ?
C9 H9 0.9300 ?
C12 C17 1.378(6) ?
C12 C13 1.383(6) yes
C13 C14 1.364(7) ?
C13 H13 0.9300 ?
C14 C15 1.399(7) ?
C14 H14 0.9300 ?
C15 C16 1.369(7) ?
C15 C18 1.499(8) ?
C16 C17 1.380(7) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
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 O1 2_565 0.86 2.17 2.929(4) 148
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 2.3(4) ?
C5 N1 N2 C8 177.7(3) ?
O2 S1 N4 C10 56.7(4) ?
O1 S1 N4 C10 -174.7(3) ?
C12 S1 N4 C10 -59.6(3) ?
F2 C1 C2 C3 62.6(9) ?
F3 C1 C2 C3 -173.7(5) ?
F1 C1 C2 C3 -51.0(7) ?
F2 C1 C2 C7 -117.5(8) ?
F3 C1 C2 C7 6.3(8) ?
F1 C1 C2 C7 128.9(6) ?
C7 C2 C3 C4 -1.5(6) ?
C1 C2 C3 C4 178.4(4) ?
C2 C3 C4 C5 1.3(6) ?
C2 C3 C4 Cl1 -177.4(3) ?
C3 C4 C5 C6 -0.4(5) ?
Cl1 C4 C5 C6 178.3(3) yes
C3 C4 C5 N1 -179.6(3) ?
Cl1 C4 C5 N1 -1.0(4) ?
C10 N1 C5 C4 78.8(5) ?
N2 N1 C5 C4 -95.8(4) ?
C10 N1 C5 C6 -100.4(4) ?
N2 N1 C5 C6 85.0(4) ?
C4 C5 C6 C7 -0.3(5) ?
N1 C5 C6 C7 179.0(3) ?
C4 C5 C6 Cl2 179.4(3) ?
N1 C5 C6 Cl2 -1.4(4) yes
C3 C2 C7 C6 0.9(6) ?
C1 C2 C7 C6 -179.1(4) ?
C5 C6 C7 C2 0.1(5) ?
Cl2 C6 C7 C2 -179.6(3) ?
N1 N2 C8 C9 -2.0(4) ?
N1 N2 C8 C11 179.5(4) ?
N2 C8 C9 C10 1.1(5) ?
C11 C8 C9 C10 179.4(4) ?
N2 N1 C10 C9 -1.7(4) yes
C5 N1 C10 C9 -176.7(3) ?
N2 N1 C10 N4 178.2(3) ?
C5 N1 C10 N4 3.2(6) yes
C8 C9 C10 N1 0.4(4) ?
C8 C9 C10 N4 -179.5(4) ?
S1 N4 C10 N1 146.7(3) ?
S1 N4 C10 C9 -33.5(6) ?
N2 C8 C11 N3 -147(13) ?
C9 C8 C11 N3 35(13) ?
O2 S1 C12 C17 0.4(4) ?
O1 S1 C12 C17 -132.8(3) yes
N4 S1 C12 C17 116.4(3) yes
O2 S1 C12 C13 -178.8(3) yes
O1 S1 C12 C13 48.0(4) ?
N4 S1 C12 C13 -62.8(3) yes
C17 C12 C13 C14 -0.4(6) ?
S1 C12 C13 C14 178.8(3) ?
C12 C13 C14 C15 0.8(7) ?
C13 C14 C15 C16 -0.4(7) ?
C13 C14 C15 C18 179.4(4) ?
C14 C15 C16 C17 -0.5(7) ?
C18 C15 C16 C17 179.8(5) ?
C13 C12 C17 C16 -0.4(6) ?
S1 C12 C17 C16 -179.6(3) ?
C15 C16 C17 C12 0.8(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126573
