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_7153690
_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         'C13 H9 Cl2 N5 O2 S'
_chemical_formula_sum            'C13 H9 Cl2 N5 O2 S'
_chemical_formula_weight         370.21
_chemical_name_systematic
;
2,3-Dichloro-N-[2-(1H-tetrazol-1-yl)phenyl]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
;
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                88.763(11)
_cell_angle_beta                 84.177(10)
_cell_angle_gamma                64.880(13)
_cell_formula_units_Z            2
_cell_length_a                   7.4390(9)
_cell_length_b                   8.4770(12)
_cell_length_c                   13.0579(15)
_cell_measurement_reflns_used    4566
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      3.03
_cell_volume                     741.50(18)
_computing_cell_refinement
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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
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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
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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 0.839
_diffrn_measurement_details
;
  1 omega  -42.00   54.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507   77.0000 -150.0000 96

  2 omega  -34.00   -8.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507   77.0000  120.0000 26

  3 omega   -1.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  -30.0000 89

  4 omega    5.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  150.0000 26

  5 omega  -17.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  120.0000 101

  6 omega  -84.00  -59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507  -38.0000 -120.0000 25

  7 omega  -66.00   28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -38.0000    0.0000 94
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_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      0.0723637000
_diffrn_orient_matrix_UB_12      -0.0045749000
_diffrn_orient_matrix_UB_13      0.0328030000
_diffrn_orient_matrix_UB_21      -0.0504190000
_diffrn_orient_matrix_UB_22      0.0913560000
_diffrn_orient_matrix_UB_23      0.0092011000
_diffrn_orient_matrix_UB_31      -0.0585496000
_diffrn_orient_matrix_UB_32      -0.0133538000
_diffrn_orient_matrix_UB_33      0.0426883000
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8747
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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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    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0025(14)
_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   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0358
_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/[\s^2^(Fo^2^)+(0.0356P)^2^+0.3323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2634
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42443j2.cif
_cod_data_source_block           16
_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_cell_volume        741.50(16)
_cod_database_code               7153690
_computing_data_merging          'SHELXTL V2008/4 (Bruker, 2008)'