Comparison of the crystal structures of the potent anticancer and anti-angiogenic agent regorafenib and its monohydrate
Sun, Meng-Ying; Wu, Su-Xiang; Zhou, Xin-Bo; Gu, Jian-Ming; Hu, Xiu-Rong; Acta Crystallographica Section C 72 (2016) 291–296; doi:10.1107/S2053229616003727

data_2020431
_publ_section_title
;
 Comparison of the crystal structures of the potent anticancer and
 anti-angiogenic agent regorafenib and its monohydrate
;
_journal_coeditor_code           KU3173
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              291
_journal_page_last               296
_journal_paper_doi               10.1107/S2053229616003727
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C21 H15 Cl F4 N4 O3, H2 O'
_chemical_formula_sum            'C21 H17 Cl F4 N4 O4'
_chemical_formula_weight         500.84
_chemical_name_common            'Regorafenib monohydrate'
_chemical_name_systematic
'4-[4-({[4-Chloro-3-(trifluoromethy)phenyl]carbamoyl}amino)-3-fluorophenoxy]-1-methylpyridine-2-carboxamide monohydrate'
_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                 92.3410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7783(2)
_cell_length_b                   21.9538(9)
_cell_length_c                   20.5581(8)
_cell_measurement_reflns_used    13751
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2154.78(15)
_computing_cell_refinement
;
PROCESS-AUTO  (Rigaku, 2006)
;
_computing_data_collection
;
PROCESS-AUTO  (Rigaku, 2006)
;
_computing_data_reduction
;
CrystalStructure (Rigaku, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz,
2005)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20501
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_correction_T_min  0.8896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.309
_refine_ls_extinction_coef       0.0203(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0538P)^2^+0.7939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                3197
_reflns_number_total             4903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ku3173sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2020430--2020431.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2020431
_cod_database_fobs_code          2020431