Repurposing the antihistamine drug bilastine as an anti-cancer metallic drug entity: synthesis and single-crystal X-ray structure analysis of metal-based bilastine and phen [Co(II), Cu(II) and Zn(II)] tailored anticancer chemotherapeutic agents against resistant cancer cells.
Rijwan, ?; Arjmand, Farukh; Tabassum, Sartaj; Dalton transactions (Cambridge, England : 2003) 53 (2024) 10126–10141; doi:10.1039/d4dt00426d

data_7716091
_publ_section_title
;
 Repurposing the antihistamine drug bilastine as an anti-cancer metallic
 drug entity: synthesis and single-crystal X-ray structure analysis of
 metal-based bilastine and phen [Co(II), Cu(II) and Zn(II)] tailored
 anticancer chemotherapeutic agents against resistant cancer cells.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10126
_journal_page_last               10141
_journal_paper_doi               10.1039/d4dt00426d
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C52 H52 Cu N7 O3, 2(H2 O), N O3, 4[H2O]'
_chemical_formula_sum            'C52 H64 Cu N8 O12'
_chemical_formula_weight         1056.65
_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
_audit_creation_date             2024-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-02 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                87.974(2)
_cell_angle_beta                 64.155(3)
_cell_angle_gamma                70.434(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8962(4)
_cell_length_b                   14.5101(3)
_cell_length_c                   15.7711(4)
_cell_measurement_reflns_used    36351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1880
_cell_measurement_theta_min      1.8550
_cell_volume                     2673.63(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            79181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.742
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1114
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         11606
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0806P)^2^+0.1151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8141
_reflns_number_total             11606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00426d2.cif
_cod_data_source_block           exp_428
_cod_depositor_comments
'Adding full bibliography for 7716091--7716093.cif.'
_cod_original_cell_volume        2673.63(13)
_cod_database_code               7716091
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N2-O3 = N2-O5
 1.25 with sigma of 0.02
 N2-O4
 1.24 with sigma of 0.02
 N2-O3 \\sim N2-O4 \\sim N2-O5
 with sigma of 0.02
 O3-O4 \\sim O4-O5 \\sim O5-O3
 with sigma of 0.04
 O3-O5 \\sim O3A-O5A
 with sigma of 0.04
 N2-O5 \\sim N2A-O5A
 with sigma of 0.02
 N2-O3 \\sim N2A-O3A
 with sigma of 0.02
3. Restrained planarity
 N2, O3, O4, O5
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N2 \\sim O3 \\sim O4 \\sim O5: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(O3A) = Uanis(O3)
Uanis(N2) = Uanis(N2A)
5. Rigid body (RIGU) restrains
 N2, O3, O4, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N2(0.75) O3(0.75) O5(0.75) O3A(0.25) N2A(0.25) O5A(0.25)
7.a Free rotating group:
 O65(H65A,H65B), O1(H1A,H1B)
7.b Ternary CH refined with riding coordinates:
 C13(H13)
7.c Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,
 H14B), C17(H17A,H17B), C15(H15A,H15B), C18(H18A,H18B), C34(H34A,H34B)
7.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C60(H60), C21(H21), C6(H6), C23(H23), C62(H62), C46(H46),
 C39(H39), C61(H61), C48(H48), C44(H44), C53(H53), C58(H58), C7(H7), C42(H42),
 C40(H40), C20(H20), C24(H24), C47(H47), C54(H54), C43(H43), C56(H56), C57(H57)
7.e Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52706
_shelx_fab_checksum              89948
_olex2_submission_special_instructions 'No special instructions were received'