Cocrystallization of axitinib with carboxylic acids: preparation, crystal structures and dissolution behavior
Ren, Bo-Ying; Dai, Xia-Lin; Wang, Jie; Wu, Chao; Lu, Tong-Bu; Chen, Jia-Mei; CrystEngComm 23 (2021) 5504–5515; doi:10.1039/D1CE00620G

data_7243195
_publ_section_title
;
 Cocrystallization of axitinib with carboxylic acids: preparation, crystal
 structures and dissolution behavior
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              5504
_journal_page_last               5515
_journal_paper_doi               10.1039/D1CE00620G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H19 N4 O S, C4 H3 O4, C2 H2 O2'
_chemical_formula_sum            'C28 H24 N4 O7 S'
_chemical_formula_weight         560.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.579(3)
_cell_angle_beta                 105.605(3)
_cell_angle_gamma                93.678(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1582(3)
_cell_length_b                   13.1348(4)
_cell_length_c                   13.1911(4)
_cell_measurement_reflns_used    10693
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.8570
_cell_measurement_theta_min      3.4630
_cell_volume                     1317.35(8)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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     52.00  88.00   0.50    0.50    --    0.00  57.00 -30.00   72
  2  \w    -21.00  51.00   0.50    0.50    --    0.00  77.00 150.00  144
  3  \w     56.00  88.00   0.50    0.50    --    0.00  77.00 150.00   64
  4  \w    -22.00  22.00   0.50    0.50    --    0.00  57.00 -30.00   88
  5  \w    -88.00  27.00   0.50    0.50    --    0.00 -57.00  90.00  230
  6  \w     93.00 133.00   0.50    1.00    --  106.20 -82.00  60.00   80
  7  \w     20.00 132.00   0.50    1.00    --  106.20 -45.00-180.00  224
  8  \w     62.00 122.00   0.50    1.00    --  106.20 -82.00 -30.00  120
  9  \w     86.00 171.00   0.50    1.00    --  106.20  30.00  60.00  170
 10  \w     73.00 146.00   0.50    1.00    --  106.20  30.00 150.00  146
 11  \w     18.00 141.00   0.50    1.00    --  106.20 -82.00-150.00  246
 12  \w     29.00  55.00   0.50    1.00    --  106.20 -82.00  60.00   52
 13  \w     18.00 126.00   0.50    1.00    --  106.20 -82.00  90.00  216
 14  \w     18.00 134.00   0.50    1.00    --  106.20 -61.00 -30.00  232
 15  \w     25.00  52.00   0.50    1.00    --  106.20 -82.00 -90.00   54
 16  \w     78.00 153.00   0.50    1.00    --  106.20  45.00-180.00  150
 17  \w    109.00 194.00   0.50    1.00    --  106.20  30.00 120.00  170
 18  \w     75.00 135.00   0.50    1.00    --  106.20 -82.00 -90.00  120
 19  \w     30.00  55.00   0.50    1.00    --  106.20 -82.00-180.00   50
 20  \w    150.00 195.00   0.50    1.00    --  106.20  30.00 150.00   90
 21  \w     44.00  70.00   0.50    1.00    --  106.20 -82.00 150.00   52
 22  \w     91.00 126.00   0.50    1.00    --  106.20 -82.00 150.00   70
 23  \w    106.00 131.00   0.50    1.00    --  106.20 -82.00   0.00   50
 24  \w     48.00  74.00   0.50    1.00    --  106.20 -82.00 120.00   52
 25  \w    105.00 132.00   0.50    1.00    --  106.20 -82.00 120.00   54
 26  \w     20.00  85.00   0.50    1.00    --  106.20 -61.00 -90.00  130
 27  \w     25.00  50.00   0.50    1.00    --  106.20 -82.00 -30.00   50
 28  \w    127.00 180.00   0.50    1.00    --  106.20  30.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0837582000
_diffrn_orient_matrix_UB_12      0.0877422000
_diffrn_orient_matrix_UB_13      -0.0475212000
_diffrn_orient_matrix_UB_21      0.1759287000
_diffrn_orient_matrix_UB_22      0.0461741000
_diffrn_orient_matrix_UB_23      -0.0039824000
_diffrn_orient_matrix_UB_31      -0.0337823000
_diffrn_orient_matrix_UB_32      -0.0697223000
_diffrn_orient_matrix_UB_33      -0.1156055000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.602
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83193
_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            Yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.7153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4972
_reflns_number_total             5560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00620g2.cif
_cod_data_source_block           axitinib_fumaricacid
_cod_depositor_comments
'Adding full bibliography for 7243193--7243195.cif.'
_cod_database_code               7243195
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.35
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C6(H6), C7(H7), C24(H24), C19(H19), C13(H13), C16(H16),
 C4(H4A), C11(H11), C14(H14), C17(H17), C1(H1A), C18(H18), C3(H3A), C28(H28),
 C2(H2), C25(H25)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6A)
;
_shelx_res_checksum              79558
_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.773