Novel pharmaceutical co-crystals of gefitinib: synthesis, dissolution, cytotoxicity, and theoretical studies
Shaik, Althaf; Bhagwat, Pranav Umesh; Palanisamy, Parimaladevi; Chhabria, Dimple; Dubey, Pankaj; Kirubakaran, Sivapriya; Thiruvenkatam, Vijay; CrystEngComm 25 (2023) 2570–2581; doi:10.1039/D3CE00056G

data_7246500
_publ_section_title
;
 Novel pharmaceutical co-crystals of gefitinib: synthesis, dissolution,
 cytotoxicity, and theoretical studies
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2570
_journal_page_last               2581
_journal_paper_doi               10.1039/D3CE00056G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C6 H6 O2, H2 O'
_chemical_formula_sum            'C28 H33 Cl F N4 O6'
_chemical_formula_weight         576.03
_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             2019-01-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-08 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.087(5)
_cell_angle_beta                 99.656(5)
_cell_angle_gamma                101.285(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1014(11)
_cell_length_b                   11.2699(15)
_cell_length_c                   15.485(2)
_cell_measurement_reflns_used    6108
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.31
_cell_volume                     1366.0(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.53
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17432
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.238
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0859 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.9087. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0427P)^2^+0.4327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5134
_reflns_number_total             6751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00056g2.cif
_cod_data_source_block           gres_0m
_cod_depositor_comments
'Adding full bibliography for 7246500--7246502.cif.'
_cod_database_code               7246500
_shelx_shelxl_version_number     2017/1
_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.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C6(H6), C7(H7), C10(H10), C11(H11), C14(H14), C2A(H2AA),
 C4A(H4A), C5A(H5A), C6A(H6A)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O2A(H2A)
;
_shelx_res_checksum              13454
_shelx_hkl_checksum              98320
_olex2_submission_special_instructions 'No special instructions were received'