Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.
Crosignani, Stefano; Page, Patrick; Missotten, Marc; Colovray, Véronique; Cleva, Christophe; Arrighi, Jean-François; Atherall, John; Macritchie, Jackie; Martin, Thierry; Humbert, Yves; Gaudet, Marilène; Pupowicz, Doris; Maio, Maurizio; Pittet, Pierre-André; Golzio, Lucia; Giachetti, Claudio; Rocha, Cynthia; Bernardinelli, Gérald; Filinchuk, Yaroslav; Scheer, Alexander; Schwarz, Matthias K.; Chollet, André; Journal of medicinal chemistry 51 (2008) 2227–2243; doi:10.1021/jm701383e

data_1504343
_publ_contact_author_email       gerald.bernardinelli@cryst.unige.ch
_publ_contact_author_fax         '+41 22 379 61 08'
_publ_contact_author_phone       '+41 22 379 62 02'
_publ_section_title
;
 Discovery of a new class of potent, selective, and orally bioavailable
 CRTH2 (DP2) receptor antagonists for the treatment of allergic
 inflammatory diseases.
;
_journal_issue                   7
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2227
_journal_page_last               2243
_journal_paper_doi               10.1021/jm701383e
_journal_volume                  51
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 Cl F N2 O5'
_chemical_formula_sum            'C20 H14 Cl F N2 O5'
_chemical_formula_weight         416.8
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-04-11
_audit_creation_method           SHELXL-97
_audit_update_record             2007-09-04
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.32926(7)
_cell_length_b                   10.77905(18)
_cell_length_c                   31.3253(5)
_cell_measurement_reflns_used    36467
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.
_cell_volume                     1799.46(5)
_computing_cell_refinement       'KUMA CrysAlis'
_computing_data_collection       'KUMA CrysAlis'
_computing_data_reduction        'KUMA CrysAlis'
_computing_molecular_graphics    xtal_gx3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'KUMA-6 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'silicon (111)'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            36467
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Abscor KUMA (CrisAlys)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          .160
_exptl_crystal_size_mid          .050
_exptl_crystal_size_min          .015
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0079(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0255P)^2^+1.3991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                3024
_reflns_number_total             3561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm701383e_si.cif
_cod_data_source_block           (R)-58
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1504343