#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/61/2206168.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_2206168
loop_
_publ_author_name
'Zhang, Xiao-Hong'
'Zhong, Ping'
'Xiao, Hong-Ping'
'Hu, Mao-Lin'
_publ_section_title
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(4-methoxyphenylsulfonamido)-1H-pyrazole-3-carbonitrile
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2134
_journal_page_last               o2135
_journal_paper_doi               10.1107/S160053680501812X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H11 Cl2 F3 N4 O3 S'
_chemical_formula_moiety         'C18 H11 Cl2 F3 N4 O3 S'
_chemical_formula_sum            'C18 H11 Cl2 F3 N4 O3 S'
_chemical_formula_weight         491.27
_chemical_melting_point          492
_chemical_name_systematic
;
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(4-methoxyphenyylsulfonamido)-
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                99.651(2)
_cell_angle_beta                 100.645(2)
_cell_angle_gamma                102.014(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3444(9)
_cell_length_b                   10.1558(10)
_cell_length_c                   11.6007(11)
_cell_measurement_reflns_used    1737
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.74
_cell_volume                     1033.65(17)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5556
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.9285
_exptl_absorpt_correction_T_min  0.8995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.457
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0780
_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)+(0.0844P)²+1.3536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.1960
_reflns_number_gt                2845
_reflns_number_total             3659
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6524.cif
_cod_data_source_block           I
_cod_database_code               2206168
_cod_database_fobs_code          2206168
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 0.23807(16) 0.16947(14) 0.54182(13) 0.0702(4) Uani d . 1 Cl
Cl2 0.25449(15) 0.55220(15) 0.92744(12) 0.0730(5) Uani d . 1 Cl
S1 0.22040(12) 0.66306(13) 0.51197(11) 0.0497(4) Uani d . 1 S
F1 -0.1390(7) -0.0028(8) 0.8354(11) 0.263(6) Uani d . 1 F
F2 -0.2590(6) 0.0450(8) 0.6996(5) 0.198(4) Uani d . 1 F
F3 -0.2253(5) 0.1591(6) 0.8662(6) 0.171(3) Uani d . 1 F
O1 0.0675(4) 0.6273(4) 0.4461(3) 0.0650(10) Uani d . 1 O
O2 0.3391(4) 0.7019(4) 0.4539(3) 0.0624(9) Uani d . 1 O
O3 0.2946(5) 1.0773(4) 0.9482(4) 0.0860(12) Uani d . 1 O
N1 0.3633(3) 0.4360(4) 0.7170(3) 0.0423(8) Uani d . 1 N
N2 0.5018(4) 0.4406(4) 0.7824(3) 0.0499(10) Uani d . 1 N
N3 0.8764(5) 0.5957(6) 0.8273(5) 0.0896(17) Uani d . 1 N
N4 0.2377(4) 0.5223(4) 0.5592(3) 0.0481(9) Uani d . 1 N
H4 0.1640 0.4501 0.5358 0.058 Uiso calc R 1 H
C1 -0.1591(7) 0.1004(7) 0.7964(7) 0.0828(19) Uani d . 1 C
C2 -0.0204(5) 0.1867(5) 0.7759(5) 0.0543(12) Uani d . 1 C
C3 0.0380(5) 0.1404(5) 0.6823(5) 0.0546(12) Uani d . 1 C
H3 -0.0069 0.0543 0.6321 0.065 Uiso calc R 1 H
C4 0.1648(5) 0.2229(5) 0.6628(4) 0.0459(10) Uani d . 1 C
C5 0.2331(4) 0.3504(4) 0.7384(4) 0.0422(10) Uani d . 1 C
C6 0.1725(5) 0.3943(5) 0.8335(4) 0.0488(11) Uani d . 1 C
C7 0.0449(5) 0.3124(5) 0.8536(4) 0.0554(12) Uani d . 1 C
H7 0.0044 0.3416 0.9180 0.067 Uiso calc R 1 H
C8 0.3683(4) 0.5167(4) 0.6361(4) 0.0396(10) Uani d . 1 C
C9 0.5159(4) 0.5811(5) 0.6497(4) 0.0469(11) Uani d . 1 C
H9 0.5566 0.6445 0.6079 0.056 Uiso calc R 1 H
C10 0.5913(4) 0.5302(5) 0.7402(4) 0.0453(11) Uani d . 1 C
C11 0.7516(5) 0.5644(6) 0.7899(5) 0.0598(13) Uani d . 1 C
C12 0.2451(5) 0.7900(5) 0.6402(4) 0.0501(11) Uani d . 1 C
C13 0.3678(5) 0.9016(5) 0.6726(5) 0.0612(13) Uani d . 1 C
H13 0.4374 0.9104 0.6248 0.073 Uiso calc R 1 H
C14 0.3880(5) 1.0000(5) 0.7752(5) 0.0633(14) Uani d . 1 C
H14 0.4706 1.0755 0.7964 0.076 Uiso calc R 1 H
C15 0.2863(6) 0.9865(5) 0.8460(5) 0.0614(13) Uani d . 1 C
C16 0.1627(6) 0.8727(6) 0.8143(5) 0.0682(15) Uani d . 1 C
H16 0.0944 0.8631 0.8631 0.082 Uiso calc R 1 H
C17 0.1421(5) 0.7761(5) 0.7128(5) 0.0615(14) Uani d . 1 C
H17 0.0593 0.7008 0.6917 0.074 Uiso calc R 1 H
C18 0.4241(7) 1.1899(6) 0.9915(6) 0.0856(18) Uani d . 1 C
H18A 0.5129 1.1556 1.0003 0.128 Uiso calc R 1 H
H18B 0.4197 1.2406 1.0679 0.128 Uiso calc R 1 H
H18C 0.4270 1.2495 0.9354 0.128 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 120.2(2) yes
O2 S1 N4 108.1(2) yes
O1 S1 N4 102.9(2) ?
O2 S1 C12 108.4(2) ?
O1 S1 C12 110.0(2) ?
N4 S1 C12 106.1(2) yes
C15 O3 C18 118.3(5) ?
C8 N1 N2 112.9(3) yes
C8 N1 C5 127.5(3) yes
N2 N1 C5 119.6(3) ?
C10 N2 N1 102.5(3) ?
C8 N4 S1 121.8(3) yes
C8 N4 H4 119.1 ?
S1 N4 H4 119.1 ?
F1 C1 F3 105.3(7) ?
F1 C1 F2 101.4(7) ?
F3 C1 F2 105.4(7) ?
F1 C1 C2 113.6(6) ?
F3 C1 C2 116.6(5) yes
F2 C1 C2 113.0(6) ?
C3 C2 C7 122.1(4) ?
C3 C2 C1 119.8(5) yes
C7 C2 C1 118.2(5) ?
C2 C3 C4 119.1(4) ?
C2 C3 H3 120.5 ?
C4 C3 H3 120.5 ?
C3 C4 C5 120.6(4) ?
C3 C4 Cl1 120.2(4) ?
C5 C4 Cl1 119.2(3) ?
C6 C5 C4 119.2(4) ?
C6 C5 N1 120.5(4) yes
C4 C5 N1 120.3(4) yes
C5 C6 C7 120.7(4) ?
C5 C6 Cl2 119.9(3) ?
C7 C6 Cl2 119.3(4) ?
C2 C7 C6 118.3(4) ?
C2 C7 H7 120.8 ?
C6 C7 H7 120.8 ?
N1 C8 C9 106.8(4) yes
N1 C8 N4 120.9(3) yes
C9 C8 N4 132.3(4) ?
C8 C9 C10 104.1(4) ?
C8 C9 H9 127.9 ?
C10 C9 H9 127.9 ?
N2 C10 C9 113.7(4) yes
N2 C10 C11 119.1(4) yes
C9 C10 C11 127.2(4) ?
N3 C11 C10 177.4(6) ?
C13 C12 C17 119.6(5) ?
C13 C12 S1 120.8(4) ?
C17 C12 S1 119.6(4) yes
C14 C13 C12 120.4(5) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C15 C14 C13 119.8(5) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
O3 C15 C14 124.8(5) ?
O3 C15 C16 115.2(5) ?
C14 C15 C16 120.0(5) ?
C17 C16 C15 120.3(5) ?
C17 C16 H16 119.9 ?
C15 C16 H16 119.9 ?
C16 C17 C12 119.9(5) yes
C16 C17 H17 120.1 ?
C12 C17 H17 120.1 ?
O3 C18 H18A 109.5 ?
O3 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O3 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 1.728(4) ?
Cl2 C6 1.715(5) ?
S1 O2 1.422(3) yes
S1 O1 1.430(3) yes
S1 N4 1.642(4) yes
S1 C12 1.742(5) yes
F1 C1 1.245(8) yes
F2 C1 1.277(8) ?
F3 C1 1.253(8) ?
O3 C15 1.353(6) yes
O3 C18 1.426(7) ?
N1 C8 1.346(5) ?
N1 N2 1.361(4) yes
N1 C5 1.428(5) yes
N2 C10 1.323(6) ?
N3 C11 1.124(6) ?
N4 C8 1.389(5) ?
N4 H4 0.8600 ?
C1 C2 1.488(7) ?
C2 C3 1.361(7) ?
C2 C7 1.380(7) ?
C3 C4 1.381(6) ?
C3 H3 0.9300 ?
C4 C5 1.386(6) yes
C5 C6 1.381(6) ?
C6 C7 1.387(6) ?
C7 H7 0.9300 ?
C8 C9 1.366(5) ?
C9 C10 1.388(6) ?
C9 H9 0.9300 ?
C10 C11 1.447(6) yes
C12 C13 1.377(7) ?
C12 C17 1.392(7) ?
C13 C14 1.375(8) ?
C13 H13 0.9300 ?
C14 C15 1.366(7) ?
C14 H14 0.9300 ?
C15 C16 1.397(7) ?
C16 C17 1.355(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_566 0.86 2.20 2.924(5) 141
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
C8 N1 N2 C10 1.5(5)
C5 N1 N2 C10 -178.8(4)
O2 S1 N4 C8 57.0(4)
O1 S1 N4 C8 -174.8(4)
C12 S1 N4 C8 -59.2(4)
F1 C1 C2 C3 72.0(10)
F3 C1 C2 C3 -165.2(7)
F2 C1 C2 C3 -42.8(9)
F1 C1 C2 C7 -108.0(9)
F3 C1 C2 C7 14.8(10)
F2 C1 C2 C7 137.2(7)
C7 C2 C3 C4 -1.4(8)
C1 C2 C3 C4 178.6(5)
C2 C3 C4 C5 0.9(7)
C2 C3 C4 Cl1 -177.9(4)
C3 C4 C5 C6 -0.2(7)
Cl1 C4 C5 C6 178.5(3)
C3 C4 C5 N1 -179.3(4)
Cl1 C4 C5 N1 -0.6(6)
C8 N1 C5 C6 -99.9(5)
N2 N1 C5 C6 80.5(5)
C8 N1 C5 C4 79.2(6)
N2 N1 C5 C4 -100.4(5)
C4 C5 C6 C7 0.0(7)
N1 C5 C6 C7 179.1(4)
C4 C5 C6 Cl2 -179.6(3)
N1 C5 C6 Cl2 -0.5(6)
C3 C2 C7 C6 1.2(8)
C1 C2 C7 C6 -178.8(5)
C5 C6 C7 C2 -0.5(7)
Cl2 C6 C7 C2 179.1(4)
N2 N1 C8 C9 -1.6(5)
C5 N1 C8 C9 178.8(4)
N2 N1 C8 N4 178.4(4)
C5 N1 C8 N4 -1.3(7)
S1 N4 C8 N1 148.3(3)
S1 N4 C8 C9 -31.8(7)
N1 C8 C9 C10 0.9(5)
N4 C8 C9 C10 -179.0(5)
N1 N2 C10 C9 -0.8(5)
N1 N2 C10 C11 179.3(4)
C8 C9 C10 N2 0.0(5)
C8 C9 C10 C11 179.8(5)
N2 C10 C11 N3 -152(13)
C9 C10 C11 N3 28(13)
O2 S1 C12 C13 -2.4(5)
O1 S1 C12 C13 -135.8(4)
N4 S1 C12 C13 113.5(4)
O2 S1 C12 C17 179.6(4)
O1 S1 C12 C17 46.3(5)
N4 S1 C12 C17 -64.4(4)
C17 C12 C13 C14 -0.8(8)
S1 C12 C13 C14 -178.8(4)
C12 C13 C14 C15 0.5(8)
C18 O3 C15 C14 -5.2(8)
C18 O3 C15 C16 174.8(5)
C13 C14 C15 O3 -179.6(5)
C13 C14 C15 C16 0.3(8)
O3 C15 C16 C17 179.1(5)
C14 C15 C16 C17 -0.8(9)
C15 C16 C17 C12 0.5(9)
C13 C12 C17 C16 0.3(8)
S1 C12 C17 C16 178.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129309
