#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:54:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180322 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/36/7153689.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_7153689
loop_
_publ_author_name
'Miah, Afjal H.'
'Copley, Royston C. B.'
'O'Flynn, Daniel'
'Percy, Jonathan M.'
'Procopiou, Panayiotis A.'
_publ_section_title
;
 Lead identification and structure-activity relationships of
 heteroarylpyrazole arylsulfonamides as allosteric CC-chemokine receptor 4
 (CCR4) antagonists.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1779
_journal_page_last               1792
_journal_paper_doi               10.1039/c3ob42443j
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C15 H11 Cl2 N3 O2 S'
_chemical_formula_sum            'C15 H11 Cl2 N3 O2 S'
_chemical_formula_weight         368.23
_chemical_name_systematic
;
2,3-Dichloro-N-[2-(1H-pyrazol-1-yl)phenyl]benzenesulfonamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.905(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5758(9)
_cell_length_b                   8.7573(9)
_cell_length_c                   23.065(2)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.65
_cell_volume                     1529.4(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_publication_material  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_refinement  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_solution    'SHELXTL V2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details
;
  1 omega  -85.00   59.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   38.0000   90.0000 144

  2 omega   -8.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  -54.0000 -153.0000 42

  3 omega  -81.00  -56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000    0.0000 25

  4 omega  -41.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  133.0000  136.0000 36
;
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      0.0007825000
_diffrn_orient_matrix_UB_12      -0.0788439000
_diffrn_orient_matrix_UB_13      0.0067273000
_diffrn_orient_matrix_UB_21      -0.0044468000
_diffrn_orient_matrix_UB_22      -0.0179527000
_diffrn_orient_matrix_UB_23      -0.0300392000
_diffrn_orient_matrix_UB_31      0.0936712000
_diffrn_orient_matrix_UB_32      -0.0005923000
_diffrn_orient_matrix_UB_33      -0.0004382000
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4880
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.76
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL V2008/4 (Bruker, 2008)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                2434
_reflns_number_total             2872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42443j2.cif
_cod_data_source_block           14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (25
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (36
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (47
times).

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153689
#BEGIN Tags that were not found in dictionaries:
_computing_data_merging          'SHELXTL V2008/4 (Bruker, 2008)'
#END Tags that were not found in dictionaries
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
C1 C 1.0091(3) 0.8897(3) 0.58755(10) 0.0216(5) Uani 1 1 d .
C2 C 0.9604(3) 0.7984(3) 0.53994(10) 0.0226(5) Uani 1 1 d .
C3 C 1.0892(3) 0.7599(3) 0.50059(10) 0.0255(5) Uani 1 1 d .
C4 C 1.2615(3) 0.8104(3) 0.50858(10) 0.0283(6) Uani 1 1 d .
H4 H 1.3480 0.7833 0.4815 0.034 Uiso 1 1 calc R
C5 C 1.3071(3) 0.8992(3) 0.55547(10) 0.0300(6) Uani 1 1 d .
H5 H 1.4253 0.9341 0.5608 0.036 Uiso 1 1 calc R
C6 C 1.1822(3) 0.9387(3) 0.59524(10) 0.0259(5) Uani 1 1 d .
H6 H 1.2152 0.9995 0.6279 0.031 Uiso 1 1 calc R
Cl7 Cl 0.74805(7) 0.73128(7) 0.52931(3) 0.02893(18) Uani 1 1 d .
Cl8 Cl 1.03505(8) 0.65106(8) 0.44018(3) 0.0358(2) Uani 1 1 d .
N9 N 0.7735(3) 0.7941(2) 0.66625(8) 0.0224(4) Uani 1 1 d .
C10 C 0.8686(3) 0.6729(3) 0.69258(9) 0.0216(5) Uani 1 1 d .
C11 C 0.8001(3) 0.5243(3) 0.68950(9) 0.0217(5) Uani 1 1 d .
C12 C 0.8943(3) 0.4058(3) 0.71529(10) 0.0293(6) Uani 1 1 d .
H12 H 0.8480 0.3051 0.7135 0.035 Uiso 1 1 calc R
C13 C 1.0547(3) 0.4318(3) 0.74361(11) 0.0353(6) Uani 1 1 d .
H13 H 1.1191 0.3490 0.7605 0.042 Uiso 1 1 calc R
C14 C 1.1213(3) 0.5776(3) 0.74747(11) 0.0364(7) Uani 1 1 d .
H14 H 1.2312 0.5958 0.7673 0.044 Uiso 1 1 calc R
C15 C 1.0282(3) 0.6975(3) 0.72256(10) 0.0295(6) Uani 1 1 d .
H15 H 1.0738 0.7982 0.7260 0.035 Uiso 1 1 calc R
N16 N 0.6343(2) 0.4910(2) 0.66082(8) 0.0221(4) Uani 1 1 d .
N17 N 0.5090(2) 0.6006(2) 0.65132(9) 0.0285(5) Uani 1 1 d .
C18 C 0.3741(3) 0.5275(3) 0.62622(11) 0.0314(6) Uani 1 1 d .
H18 H 0.2661 0.5749 0.6142 0.038 Uiso 1 1 calc R
C19 C 0.4097(3) 0.3731(3) 0.61957(11) 0.0334(6) Uani 1 1 d .
H19 H 0.3341 0.2972 0.6029 0.040 Uiso 1 1 calc R
C20 C 0.5761(3) 0.3543(3) 0.64204(11) 0.0307(6) Uani 1 1 d .
H20 H 0.6400 0.2610 0.6441 0.037 Uiso 1 1 calc R
S21 S 0.85383(7) 0.94706(7) 0.63964(2) 0.02290(17) Uani 1 1 d .
O22 O 0.70788(19) 1.02100(18) 0.61052(7) 0.0271(4) Uani 1 1 d .
O23 O 0.9535(2) 1.02902(19) 0.68323(7) 0.0315(4) Uani 1 1 d .
H9 H 0.675(3) 0.770(3) 0.6549(10) 0.020(7) Uiso 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.09232
-1 0 0 0.09232
0 1 0 0.21719
0 -1 0 0.21719
0 0 1 0.05541
0 0 -1 0.05541
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
C6 C1 C2 120.1(2) y
C6 C1 S21 118.00(17) y
C2 C1 S21 121.90(17) y
C3 C2 C1 118.5(2) y
C3 C2 Cl7 119.66(18) y
C1 C2 Cl7 121.85(17) y
C4 C3 C2 120.8(2) y
C4 C3 Cl8 118.79(18) y
C2 C3 Cl8 120.36(18) y
C5 C4 C3 120.0(2) y
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C4 C5 C6 120.4(2) y
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
C5 C6 C1 120.2(2) y
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
C10 N9 S21 126.84(16) y
C10 N9 H9 113.5(17) ?
S21 N9 H9 116.6(17) ?
C15 C10 C11 118.9(2) y
C15 C10 N9 121.5(2) y
C11 C10 N9 119.6(2) y
C12 C11 C10 119.3(2) y
C12 C11 N16 118.6(2) y
C10 C11 N16 122.1(2) y
C13 C12 C11 120.9(2) y
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
C14 C13 C12 120.0(2) y
C14 C13 H13 120.0 ?
C12 C13 H13 120.0 ?
C13 C14 C15 119.9(2) y
C13 C14 H14 120.1 ?
C15 C14 H14 120.1 ?
C14 C15 C10 120.9(2) y
C14 C15 H15 119.5 ?
C10 C15 H15 119.5 ?
C20 N16 N17 110.88(19) y
C20 N16 C11 127.2(2) y
N17 N16 C11 121.84(18) y
C18 N17 N16 104.7(2) y
N17 C18 C19 111.7(2) y
N17 C18 H18 124.2 ?
C19 C18 H18 124.2 ?
C20 C19 C18 104.9(2) y
C20 C19 H19 127.5 ?
C18 C19 H19 127.5 ?
N16 C20 C19 107.8(2) y
N16 C20 H20 126.1 ?
C19 C20 H20 126.1 ?
O22 S21 O23 119.02(10) y
O22 S21 N9 105.14(10) y
O23 S21 N9 110.41(10) y
O22 S21 C1 109.18(10) y
O23 S21 C1 105.70(10) y
N9 S21 C1 106.87(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.385(3) y
C1 C2 1.398(3) y
C1 S21 1.782(2) y
C2 C3 1.396(3) y
C2 Cl7 1.723(2) y
C3 C4 1.384(3) y
C3 Cl8 1.726(2) y
C4 C5 1.367(3) y
C4 H4 0.9500 ?
C5 C6 1.383(3) y
C5 H5 0.9500 ?
C6 H6 0.9500 ?
N9 C10 1.409(3) y
N9 S21 1.602(2) y
N9 H9 0.81(2) ?
C10 C15 1.389(3) y
C10 C11 1.402(3) y
C11 C12 1.383(3) y
C11 N16 1.430(3) y
C12 C13 1.379(3) y
C12 H12 0.9500 ?
C13 C14 1.375(4) y
C13 H13 0.9500 ?
C14 C15 1.379(3) y
C14 H14 0.9500 ?
C15 H15 0.9500 ?
N16 C20 1.343(3) y
N16 N17 1.363(3) y
N17 C18 1.323(3) y
C18 C19 1.389(4) y
C18 H18 0.9500 ?
C19 C20 1.357(3) y
C19 H19 0.9500 ?
C20 H20 0.9500 ?
S21 O22 1.4296(16) y
S21 O23 1.4304(16) y
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
N9 H9 N17 0.81(2) 1.95(2) 2.638(3) 143(2)
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
C6 C1 C2 C3 -0.6(3) y
S21 C1 C2 C3 179.15(17) y
C6 C1 C2 Cl7 178.61(17) y
S21 C1 C2 Cl7 -1.6(3) y
C1 C2 C3 C4 0.3(3) y
Cl7 C2 C3 C4 -179.00(18) y
C1 C2 C3 Cl8 -178.55(17) y
Cl7 C2 C3 Cl8 2.2(3) y
C2 C3 C4 C5 -0.1(4) y
Cl8 C3 C4 C5 178.74(19) y
C3 C4 C5 C6 0.3(4) y
C4 C5 C6 C1 -0.7(4) y
C2 C1 C6 C5 0.8(4) y
S21 C1 C6 C5 -178.94(18) y
S21 N9 C10 C15 30.7(3) y
S21 N9 C10 C11 -150.44(18) y
C15 C10 C11 C12 -1.3(3) y
N9 C10 C11 C12 179.8(2) y
C15 C10 C11 N16 178.2(2) y
N9 C10 C11 N16 -0.7(3) y
C10 C11 C12 C13 -0.4(3) y
N16 C11 C12 C13 -179.8(2) y
C11 C12 C13 C14 1.3(4) y
C12 C13 C14 C15 -0.5(4) y
C13 C14 C15 C10 -1.1(4) y
C11 C10 C15 C14 2.0(3) y
N9 C10 C15 C14 -179.1(2) y
C12 C11 N16 C20 -19.0(3) y
C10 C11 N16 C20 161.5(2) y
C12 C11 N16 N17 158.1(2) y
C10 C11 N16 N17 -21.4(3) y
C20 N16 N17 C18 -0.2(2) y
C11 N16 N17 C18 -177.8(2) y
N16 N17 C18 C19 0.2(3) y
N17 C18 C19 C20 -0.1(3) y
N17 N16 C20 C19 0.2(3) y
C11 N16 C20 C19 177.5(2) y
C18 C19 C20 N16 0.0(3) y
C10 N9 S21 O22 171.30(18) y
C10 N9 S21 O23 -59.2(2) y
C10 N9 S21 C1 55.3(2) y
C6 C1 S21 O22 125.10(18) y
C2 C1 S21 O22 -54.7(2) y
C6 C1 S21 O23 -4.0(2) y
C2 C1 S21 O23 176.17(18) y
C6 C1 S21 N9 -121.68(19) y
C2 C1 S21 N9 58.5(2) y
