Mechanism of solvent-mediated polymorphic transformation to prepare axitinib form XLI controlled by water activity
Li, Tong; Zhang, Jin; Li, Maolin; Qu, Haibin; Wu, Songgu; Gong, Junbo; CrystEngComm 26 (2024) 6562–6572; doi:10.1039/D4CE00863D

data_7249473
_publ_section_title
;
 Mechanism of solvent-mediated polymorphic transformation to prepare
 axitinib form XLI controlled by water activity
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              6562
_journal_page_last               6572
_journal_paper_doi               10.1039/D4CE00863D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H18 N4 O S, C H4 O'
_chemical_formula_sum            'C23 H22 N4 O2 S'
_chemical_formula_weight         418.50
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-03 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                66.228(12)
_cell_angle_beta                 89.807(8)
_cell_angle_gamma                74.215(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6162(7)
_cell_length_b                   12.3399(17)
_cell_length_c                   12.7919(13)
_cell_measurement_reflns_used    3610
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.8660
_cell_measurement_theta_min      1.7310
_cell_volume                     1051.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -120.00  60.00   0.50    3.00    --  -30.00  15.00  90.00  360
  2  \w   -120.00  14.00   0.50    3.00    --  -30.00 -70.00 180.00  268
  3  \w    -74.00  60.00   0.50    3.00    --  -30.00  70.00   0.00  268
  4  \w   -120.00  14.00   0.50    3.00    --  -30.00 -70.00   0.00  268
  5  \w    -74.00  52.00   0.50    3.00    --  -30.00  70.00 180.00  252
  6  \w   -120.00   0.00   0.50    3.00    --  -30.00  15.00   0.00  240
  7  \w    -74.00  39.00   0.50    3.00    --  -30.00  70.00  90.00  226
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0192250000
_diffrn_orient_matrix_UB_12      -0.0574725000
_diffrn_orient_matrix_UB_13      0.0490139000
_diffrn_orient_matrix_UB_21      -0.0210483000
_diffrn_orient_matrix_UB_22      0.0319157000
_diffrn_orient_matrix_UB_23      0.0359263000
_diffrn_orient_matrix_UB_31      -0.0932312000
_diffrn_orient_matrix_UB_32      0.0012792000
_diffrn_orient_matrix_UB_33      -0.0057079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2022
_diffrn_reflns_av_unetI/netI     0.1589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         1.752
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1879
_refine_ls_R_factor_gt           0.1375
_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^)+(0.1741P)^2^+3.0837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3422
_refine_ls_wR_factor_ref         0.3747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2743
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00863d2.cif
_cod_data_source_block           r20230618b_autored
_cod_depositor_comments          'Adding full bibliography for 7249473.cif.'
_cod_database_code               7249473
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.953
_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. Restrained distances
 N1-H1
 0.9 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
3.b Fitted hexagon refined as free rotating group:
 C7(C8,C3,C4,C5,C6)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_shelx_res_checksum              70671
_shelx_hkl_checksum              68473
_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 9.570
_oxdiff_exptl_absorpt_empirical_full_min 0.275