Sorafenib and its tosylate salt: a multikinase inhibitor for treating cancer
Ravikumar, K.; Sridhar, B.; Bhujanga Rao, A. K. S.; Pulla Reddy, M.; Acta Crystallographica Section C 67 (2011) o29–o32; doi:10.1107/S0108270110047451

data_2017920
_publ_section_title
;
 Sorafenib and its tosylate salt: a multikinase inhibitor for treating
 cancer
;
_journal_coeditor_code           DN3155
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o29
_journal_page_last               o32
_journal_paper_doi               10.1107/S0108270110047451
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H16 Cl F3 N4 O3'
_chemical_formula_moiety         'C21 H16 Cl F3 N4 O3'
_chemical_formula_sum            'C21 H16 Cl F3 N4 O3'
_chemical_formula_weight         464.83
_chemical_name_systematic
;
4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-
<i>N</i>-methylpyridine-2-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.358(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1587(16)
_cell_length_b                   9.8055(19)
_cell_length_c                   27.758(5)
_cell_measurement_reflns_used    7634
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.20
_cell_volume                     2214.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0189
_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       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            20023
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0506P)^2^+0.5662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3241
_reflns_number_total             3896
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            dn3155.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017920