Cocrystals of regorafenib with dicarboxylic acids: synthesis, characterization and property evaluation
Jia, Jun-Long; Dai, Xia-Lin; Che, Hao-Jie; Li, Meng-Ting; Zhuang, Xiao-Mei; Lu, Tong-Bu; Chen, Jia-Mei; CrystEngComm 23 (2021) 653–662; doi:10.1039/D0CE01341B

data_7241556
_publ_section_title
;
 Cocrystals of regorafenib with dicarboxylic acids: synthesis,
 characterization and property evaluation
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              653
_journal_page_last               662
_journal_paper_doi               10.1039/D0CE01341B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C21 H15 Cl F4 N4 O3, C5 H8 O4'
_chemical_formula_sum            'C26 H23 Cl F4 N4 O7'
_chemical_formula_weight         614.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-31 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.6243(3)
_cell_length_b                   7.42220(10)
_cell_length_c                   15.1901(2)
_cell_measurement_reflns_used    10414
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.0170
_cell_measurement_theta_min      3.7950
_cell_volume                     2630.43(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -17.00  31.00   0.50    0.50    --    0.00 -77.00-180.00   96
  2  \w     41.00  87.00   0.50    0.50    --    0.00  57.00-120.00   92
  3  \w     45.00  89.00   0.50    0.50    --    0.00  82.00 -90.00   88
  4  \w    -28.00  23.00   0.50    0.50    --    0.00  57.00-120.00  102
  5  \w    -46.00   3.00   0.50    0.50    --    0.00  19.00-180.00   98
  6  \w     17.00 138.00   0.50    2.60    --  106.20 -82.00 -60.00  242
  7  \w     49.00 141.00   0.50    2.60    --  106.20 -77.00  60.00  184
  8  \w    156.00 191.00   0.50    2.60    --  106.20  30.00 -90.00   70
  9  \w    129.00 196.00   0.50    2.60    --  106.20  77.00  30.00  134
 10  \w     32.00  88.00   0.50    2.60    --  106.20 -45.00  60.00  112
 11  \w     73.00 150.00   0.50    2.60    --  106.20  30.00 -90.00  154
 12  \w     31.00 134.00   0.50    2.60    --  106.20 -45.00 -60.00  206
 13  \w     17.00  66.00   0.50    2.60    --  106.20 -77.00-180.00   98
 14  \w     87.00 112.00   0.50    2.60    --  106.20 -77.00-180.00   50
 15  \w     90.00 123.00   0.50    2.60    --  106.20 -82.00-120.00   66
 16  \w    142.00 193.00   0.50    2.60    --  106.20  15.00 120.00  102
 17  \w     25.00 100.00   0.50    2.60    --  106.20  15.00 120.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236605000
_diffrn_orient_matrix_UB_12      0.1897924000
_diffrn_orient_matrix_UB_13      0.0133395000
_diffrn_orient_matrix_UB_21      -0.0613040000
_diffrn_orient_matrix_UB_22      -0.0769038000
_diffrn_orient_matrix_UB_23      -0.0114521000
_diffrn_orient_matrix_UB_31      0.0066764000
_diffrn_orient_matrix_UB_32      -0.0337872000
_diffrn_orient_matrix_UB_33      0.1011454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17014
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         3.789
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.6726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4298
_reflns_number_total             4692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01341b2.cif
_cod_data_source_block           200528-2-jjl
_cod_depositor_comments          'Adding full bibliography for 7241556.cif.'
_cod_database_code               7241556
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F5)
3. Others
 Sof(H14)=Sof(F5)=1-FVAR(1)
 Sof(F4)=Sof(H10)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B), C24(H24A,H24B)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), N2(H2), C3(H3), C14(H14), C16(H16), C10(H10), C11(H11),
 C13(H13), C5(H5), C19(H19), C6(H6), C18(H18)
4.c Tetrahedral OH refined with riding coordinates:
 O7(H7)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_shelx_res_checksum              83323
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.871
_oxdiff_exptl_absorpt_empirical_full_min 0.418