Serendipitous discovery of a novel polymorph of an immunosuppressant drug azathioprine: phase transformation, solubility, dissolution and stability study
Kalavalapudi, Likhitha; Palani, Sivanarayanan; Nechipadappu, Sunil Kumar; CrystEngComm 26 (2024) 5187–5201; doi:10.1039/D4CE00589A

data_7249212
_publ_section_title
;
 Serendipitous discovery of a novel polymorph of an immunosuppressant drug
 azathioprine: phase transformation, solubility, dissolution and stability
 study
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              5187
_journal_page_last               5201
_journal_paper_doi               10.1039/D4CE00589A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C9 H7 N7 O2 S, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C11 H11 N7 O3 S'
_chemical_formula_weight         321.33
_chemical_name_common            'Azathioprine-hemidioxane solvate'
_chemical_name_systematic        'Azathioprine-hemidioxane solvate'
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-06-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.035(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4622(8)
_cell_length_b                   15.295(2)
_cell_length_c                   19.852(3)
_cell_measurement_reflns_used    2886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.987
_cell_measurement_theta_min      2.663
_cell_volume                     1354.0(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.1101
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12611
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.631
_diffrn_reflns_theta_min         2.447
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,4-Dioxane'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0758P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             3385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00589a2.cif
_cod_data_source_block           KB1331_0m
_cod_depositor_comments
'Adding full bibliography for 7249210--7249213.cif.'
_cod_original_cell_volume        1354.1(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249212
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.951
_shelx_res_checksum              45649