A current insight into the drug–drug molecular adducts of an anti-cancer drug vandetanib with various NSAIDs
Abishek, K. G.; Kenguva, Gowtham; Giri, Lopamudra; Venkat Shivaji Ramarao, E. V.; Dhilli Rao, Gorja; Dandela, Rambabu; CrystEngComm 27 (2025) 2998–3005; doi:10.1039/D5CE00070J

data_7250631
_publ_section_title
;
 A current insight into the drug--drug molecular adducts of an anti-cancer
 drug vandetanib with various NSAIDs
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2998
_journal_page_last               3005
_journal_paper_doi               10.1039/D5CE00070J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C22 H25 Br F N4 O2, C15 H14 N O2'
_chemical_formula_sum            'C37 H39 Br F N5 O4'
_chemical_formula_weight         716.64
_chemical_name_common            'Vandetanib Mefenamic acid'
_chemical_name_systematic
'4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)-1-methylpiperidin-1-ium 2-((2,3-dimethylphenyl)amino)benzoate'
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-27 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                110.597(2)
_cell_angle_beta                 90.033(2)
_cell_angle_gamma                118.704(2)
_cell_formula_units_Z            2
_cell_length_a                   12.7596(10)
_cell_length_b                   12.7738(10)
_cell_length_c                   13.1770(11)
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      3.19
_cell_volume                     1725.4(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_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      298.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33222
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.238
_diffrn_source                   microfocus
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.8594.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0542P)^2^+2.0660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5068
_reflns_number_total             7912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00070j2.cif
_cod_data_source_block           vndb_mfa
_cod_database_code               7250631
_shelx_shelxl_version_number     2018/3
_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
2.a Ternary CH refined with riding coordinates:
 N1(H1), C4(H4A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C9(H9), C12(H12), C15(H15), C19(H19), C21(H21), C22(H22), N5(H5),
 C25(H25), C26(H26), C27(H27), C32(H32), C33(H33), C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              81979
_olex2_submission_special_instructions 'No special instructions were received'