Two anhydrous forms and one monohydrate of a cocrystal of axitinib and glutaric acid: characterization, property evaluation and phase transition study
Ren, Bo-Ying; Dai, Xia-Lin; Chen, Jia-Mei; Lu, Tong-Bu; CrystEngComm  (2022) –; doi:10.1039/D1CE01740C

data_7244532
_publ_section_title
;
 Two anhydrous forms and one monohydrate of a cocrystal of axitinib and
 glutaric acid: characterization, property evaluation and phase transition
 study
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01740C
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 N4 O S, C5 H7.997 O4, H2 O'
_chemical_formula_sum            'C27 H28 N4 O6 S'
_chemical_formula_weight         536.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-11-28
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-11-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1885(2)
_cell_length_b                   7.66640(10)
_cell_length_c                   22.5682(3)
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.7360
_cell_measurement_theta_min      3.8910
_cell_volume                     2627.60(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2016/6 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -30.00  22.00   0.50    0.69    --    0.00 -57.00  60.00  104
  2  \w    -87.00  27.00   0.50    0.69    --    0.00 -57.00 -30.00  228
  3  \w    -81.00 -56.00   0.50    0.69    --    0.00 -57.00 -60.00   50
  4  \w    -81.00 -41.00   0.50    0.69    --    0.00 -57.00  60.00   80
  5  \w    -19.00   6.00   0.50    0.69    --    0.00 -57.00 -60.00   50
  6  \w     21.00 140.00   0.50    4.00    --  106.20 -30.00 150.00  238
  7  \w     52.00 112.00   0.50    4.00    --  106.20 -77.00 -30.00  120
  8  \w    169.00 195.00   0.50    4.00    --  106.20 -15.00 -30.00   52
  9  \w     75.00 110.00   0.50    4.00    --  106.20 -82.00  30.00   70
 10  \w     37.00  66.00   0.50    4.00    --  106.20 -82.00  30.00   58
 11  \w     99.00 125.00   0.50    4.00    --  106.20 -61.00-150.00   52
 12  \w     34.00 133.00   0.50    4.00    --  106.20 -30.00  30.00  198
 13  \w     17.00 134.00   0.50    4.00    --  106.20 -45.00 -60.00  234
 14  \w     35.00 138.00   0.50    4.00    --  106.20 -77.00  60.00  206
 15  \w    103.00 149.00   0.50    4.00    --  106.20 -15.00 -30.00   92
 16  \w     33.00  84.00   0.50    4.00    --  106.20 -15.00 -30.00  102
;
_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      -0.0755688000
_diffrn_orient_matrix_UB_12      -0.0210599000
_diffrn_orient_matrix_UB_13      -0.0457452000
_diffrn_orient_matrix_UB_21      0.0675932000
_diffrn_orient_matrix_UB_22      -0.0305916000
_diffrn_orient_matrix_UB_23      -0.0491263000
_diffrn_orient_matrix_UB_31      -0.0024605000
_diffrn_orient_matrix_UB_32      -0.1975007000
_diffrn_orient_matrix_UB_33      0.0125018000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15717
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58093
_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            white
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       flake
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4696
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0759P)^2^+2.2471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4096
_reflns_number_total             4696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01740c2.cif
_cod_data_source_block           rby0526
_cod_database_code               7244532
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.752
_reflns_odcompleteness_completeness 99.86
_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, All O(H,H) groups
2. Restrained distances
 C30-C29
 1.54 with sigma of 0.02
 H6A-O6
 0.82 with sigma of 0.01
 C31-O8
 1.2 with sigma of 0.02
 O9-C31
 1.28 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C30)
Uanis(C24) = Uanis(C32)
Uanis(C27) = Uanis(C31)
Uanis(C26) = Uanis(C29)
Uanis(O4) = Uanis(O8)
Uanis(O2) = Uanis(O11)
Uanis(O5) = Uanis(O7)
Uanis(C23) = Uanis(C342)
Uanis(O6) = Uanis(O10)
Uanis(O3) = Uanis(O9)
4. Others
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(C32)=
 Sof(H32A)=Sof(H32B)=Sof(C342)=Sof(O10)=Sof(H10)=Sof(O7)=Sof(O8)=Sof(O9)=
 Sof(H9)=1-FVAR(1)
 Sof(C23)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(O6)=Sof(O3)=Sof(H3B)=Sof(O5)=Sof(O4)=FVAR(1)
 Sof(O11)=Sof(H11A)=Sof(H11B)=1-FVAR(2)
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(2)
 Fixed Sof: H6A(0.78)
5.a Riding coordinates:
 O3(H3B), O9(H9)
5.b Free rotating group:
 O2(H2A,H2B), O11(H11A,H11B)
5.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C29(H29A,H29B), C30(H30A,
 H30B), C32(H32A,H32B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), N4(H4A), N3(H3A)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
5.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
;
_shelx_res_checksum              51201
_shelx_hkl_checksum              28329
_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 1.909
_oxdiff_exptl_absorpt_empirical_full_min 0.540