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_7243194
_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 H18 N4 O S, C9 H8 O2'
_chemical_formula_sum            'C31 H26 N4 O3 S'
_chemical_formula_weight         534.62
_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             2021-07-06
_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                62.9890(10)
_cell_angle_beta                 82.2420(10)
_cell_angle_gamma                79.9120(10)
_cell_formula_units_Z            2
_cell_length_a                   7.85120(10)
_cell_length_b                   13.6163(2)
_cell_length_c                   14.6035(2)
_cell_measurement_reflns_used    10957
_cell_measurement_temperature    275(4)
_cell_measurement_theta_max      79.0600
_cell_measurement_theta_min      5.6830
_cell_volume                     1366.64(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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      air
_diffrn_ambient_temperature      275(4)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_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    -73.00 -47.00   0.50    0.50    --    0.00 -53.00  99.00   52
  2  \w    -40.00  26.00   0.50    0.50    --    0.00 -53.00  99.00  132
  3  \w     23.00  71.00   0.50    1.00    --  105.20 -53.00  99.00   96
  4  \w     91.00 130.00   0.50    1.00    --  105.20 -53.00  99.00   78
  5  \w     47.00  89.00   0.50    0.50    --    0.00  57.00 -30.00   84
  6  \w    -88.00  15.00   0.50    0.50    --    0.00 -37.00   0.00  206
  7  \w    -26.00  38.00   0.50    0.50    --    0.00  57.00 -30.00  128
  8  \w      0.00  31.00   0.50    0.50    --    0.00  53.00-115.00   62
  9  \w     16.00  89.00   0.50    1.00    --  105.20 -30.00 -90.00  146
 10  \w     16.00 141.00   0.50    1.00    --  105.20 -82.00 -90.00  250
 11  \w     16.00  63.00   0.50    1.00    --  105.20 -61.00 -90.00   94
 12  \w     64.00 131.00   0.50    1.00    --  105.20 -82.00-120.00  134
 13  \w     27.00 140.00   0.50    1.00    --  105.20 -82.00  90.00  226
 14  \w     17.00 141.00   0.50    1.00    --  105.20 -82.00   0.00  248
 15  \w     20.00  47.00   0.50    1.00    --  105.20 -82.00 150.00   54
 16  \w     70.00 139.00   0.50    1.00    --  105.20 -82.00 150.00  138
 17  \w     99.00 124.00   0.50    1.00    --  105.20  61.00 -30.00   50
 18  \w    166.00 195.00   0.50    1.00    --  105.20  61.00 -30.00   58
 19  \w    140.00 166.00   0.50    1.00    --  105.20  30.00-150.00   52
 20  \w     17.00 136.00   0.50    1.00    --  105.20 -30.00   0.00  238
 21  \w     76.00 132.00   0.50    1.00    --  105.20  30.00-150.00  112
 22  \w     20.00  48.00   0.50    1.00    --  105.20 -82.00-120.00   56
 23  \w    108.00 133.00   0.50    1.00    --  105.20 -61.00 -90.00   50
 24  \w     24.00  70.00   0.50    1.00    --  105.20 -77.00 -60.00   92
 25  \w     21.00  61.00   0.50    1.00    --  105.20  15.00-180.00   80
 26  \w     65.00 194.00   0.50    1.00    --  105.20  15.00-180.00  258
 27  \w     40.00  86.00   0.50    1.00    --  105.20 -77.00  30.00   92
 28  \w     88.00 113.00   0.50    1.00    --  105.20  77.00 -60.00   50
 29  \w    170.00 195.00   0.50    1.00    --  105.20  77.00 -60.00   50
 30  \w     78.00 103.00   0.50    1.00    --  105.20 -82.00 -30.00   50
 31  \w     98.00 123.00   0.50    1.00    --  105.20  53.00-115.00   50
;
_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      -0.1001782000
_diffrn_orient_matrix_UB_12      -0.0173565000
_diffrn_orient_matrix_UB_13      -0.0741177000
_diffrn_orient_matrix_UB_21      -0.1542422000
_diffrn_orient_matrix_UB_22      0.0816501000
_diffrn_orient_matrix_UB_23      0.0114718000
_diffrn_orient_matrix_UB_31      0.0778090000
_diffrn_orient_matrix_UB_32      0.0971197000
_diffrn_orient_matrix_UB_33      -0.0919337000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18224
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.421
_diffrn_reflns_theta_min         3.748
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1065P)^2^+0.1468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5131
_reflns_number_total             5765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00620g2.cif
_cod_data_source_block           axitinibtranscinnamicacid
_cod_depositor_comments
'Adding full bibliography for 7243193--7243195.cif.'
_cod_database_code               7243194
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.21
_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
2. Restrained distances
 O2-H2A
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C11(H11), C14(H14), C7(H7), C16(H16), C6(H6), C13(H13),
 C19(H19), C4(H4A), C25(H25), C17(H17), C27(H27), C1(H1), C18(H18), C3(H3A),
 C2(H2), C24(H24), C28(H28), C31(H31), C29(H29), C30(H30)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              55759
_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 3.438
_oxdiff_exptl_absorpt_empirical_full_min 0.363