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_7153687
_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 H13 Cl2 N3 O3 S'
_chemical_formula_sum            'C15 H13 Cl2 N3 O3 S'
_chemical_formula_weight         386.24
_chemical_name_systematic
;
2,3-Dichloro-N-[1-methyl-4-(methyloxy)-1H-indazol-3-yl]benzenesulfonamide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.664(17)
_cell_angle_beta                 99.981(17)
_cell_angle_gamma                97.378(14)
_cell_formula_units_Z            4
_cell_length_a                   7.9294(12)
_cell_length_b                   12.763(2)
_cell_length_c                   16.761(3)
_cell_measurement_reflns_used    7125
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1640.1(5)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'COLLECT (Nonius, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'normal focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15975
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         5.16
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       wedge
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0299P)^2^+1.0816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                4964
_reflns_number_total             5632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42443j2.cif
_cod_data_source_block           7
_cod_database_code               7153687
_computing_data_merging          'SHELXTL V6.12 (Bruker, 2001)'