Lead identification and structure-activity relationships of heteroarylpyrazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists.
Miah, Afjal H.; Copley, Royston C. B.; O'Flynn, Daniel; Percy, Jonathan M.; Procopiou, Panayiotis A.; Organic & biomolecular chemistry 12 (2014) 1779–1792; doi:10.1039/c3ob42443j

data_7153689
_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 &amp; 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0370P)^2^+0.1512P] where P=(Fo^2^+2Fc^2^)/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
_computing_data_merging          'SHELXTL V2008/4 (Bruker, 2008)'