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_7249213
_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         '2(C9 H7 N7 O2 S), C3 H8 O2, H2 O'
_chemical_formula_sum            'C21 H24 N14 O7 S2'
_chemical_formula_weight         648.66
_chemical_name_common            'Azathioprine-2-methoxyethanol hydrate'
_chemical_name_systematic        'Azathioprine-2-methoxyethanol hydrate'
_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
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_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                 91.152(6)
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_cell_formula_units_Z            4
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_cell_length_b                   25.0168(19)
_cell_length_c                   24.5692(18)
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      2.32
_cell_volume                     2691.0(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'
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_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35022
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
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_diffrn_reflns_theta_max         29.123
_diffrn_reflns_theta_min         2.324
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6018
_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_density_diffrn    1.601
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_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 2-methoxyethanol+formamide'
_exptl_crystal_size_max          0.200
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_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0703
_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^)+(0.0812P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3547
_reflns_number_total             6784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00589a2.cif
_cod_data_source_block           KB1287_0m
_cod_depositor_comments
'Adding full bibliography for 7249210--7249213.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249213
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              7534