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_7716092
_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 N7 O3 Zn, Cl O4, C3 H7 N O'
_chemical_formula_sum            'C55 H59 Cl N8 O8 Zn'
_chemical_formula_weight         1060.92
_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             2024-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-05-02 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                89.321(2)
_cell_angle_beta                 78.8850(10)
_cell_angle_gamma                81.020(2)
_cell_formula_units_Z            2
_cell_length_a                   12.4495(2)
_cell_length_b                   14.2858(4)
_cell_length_c                   15.3421(2)
_cell_measurement_reflns_used    29616
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0100
_cell_measurement_theta_min      1.9380
_cell_volume                     2644.14(9)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     30.00  56.00   0.50   11.50    --  -11.09  19.00   0.00   52
  2  \w    -16.00  79.00   0.50   11.50    --   10.55  77.00 -60.00  190
  3  \w    -13.00  54.00   0.50   11.50    --   10.55  77.00 120.00  134
  4  \w    -26.00  47.00   0.50   11.50    --  -11.09  37.00 -90.00  146
  5  \w    -21.00  55.00   0.50   11.50    --  -11.09  37.00-180.00  152
  6  \w    -33.00  -7.00   0.50   11.50    --  -11.09 -57.00-180.00   52
  7  \w    -23.00  46.00   0.50   11.50    --   10.55 -99.00-180.00  138
  8  \w      7.00  57.00   0.50   11.50    --   10.55-118.00-131.00  100
  9  \w     17.00  61.00   0.50   11.50    --   10.55-125.00 -30.00   88
 10  \w     30.00  82.00   0.50   11.50    --   10.55-159.00  75.00  104
 11  \w    -23.00  41.00   0.50   11.50    --   10.55 -99.00   0.00  128
 12  \w     -5.00  21.00   0.50   11.50    --   10.55 -99.00  60.00   52
 13  \w    -14.00  36.00   0.50   11.50    --   10.55 -99.00 120.00  100
 14  \w    -13.00  13.00   0.50   11.50    --  -11.09 -99.00  90.00   52
 15  \w    -21.00  19.00   0.50   11.50    --  -11.09 -99.00 150.00   80
 16  \w    -26.00  16.00   0.50   11.50    --  -11.09 -77.00  30.00   84
 17  \w    -13.00  20.00   0.50   11.50    --  -11.09 -99.00 -30.00   66
 18  \w    -21.00  31.00   0.50   11.50    --   10.55 -99.00 -90.00  104
 19  \w    -20.00  21.00   0.50   11.50    --  -11.09 -99.00   0.00   82
 20  \w    -22.00   8.00   0.50   11.50    --  -11.09 -99.00 -90.00   60
 21  \w    -23.00  24.00   0.50   11.50    --  -11.09 -99.00-120.00   94
 22  \w    -21.00   4.00   0.50   11.50    --  -11.09 -99.00-180.00   50
 23  \w    -55.00   4.00   0.50   11.50    --   10.55 -19.00-180.00  118
 24  \w    -62.00   5.00   0.50   11.50    --   10.55 -19.00-120.00  134
 25  \w    -62.00   2.00   0.50   11.50    --   10.55 -19.00 -60.00  128
 26  \w    -57.00  23.00   0.50   11.50    --   10.55 -57.00  30.00  160
 27  \w    -59.00   5.00   0.50   11.50    --   10.55 -19.00 -90.00  128
 28  \w    -77.00 -39.00   0.50   11.50    --  -11.09 -77.00  30.00   76
 29  \w    -79.00  10.00   0.50   11.50    --  -11.09 -57.00 -30.00  178
 30  \w    -79.00 -35.00   0.50   11.50    --  -11.09 -57.00-180.00   88
 31  \w    -83.00   5.00   0.50   11.50    --  -11.09 -19.00   0.00  176
 32  \w    -81.00 -15.00   0.50   11.50    --  -11.09 -19.00  90.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0112913000
_diffrn_orient_matrix_UB_12      -0.0501564000
_diffrn_orient_matrix_UB_13      0.0014990000
_diffrn_orient_matrix_UB_21      0.0037945000
_diffrn_orient_matrix_UB_22      -0.0028437000
_diffrn_orient_matrix_UB_23      -0.0466469000
_diffrn_orient_matrix_UB_31      0.0575708000
_diffrn_orient_matrix_UB_32      0.0019767000
_diffrn_orient_matrix_UB_33      -0.0065217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9281
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.949
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73399
_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            coloress
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          .29
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .19
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     664
_refine_ls_number_reflns         9281
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0721
_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^)+(0.1101P)^2^+1.8746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6410
_reflns_number_total             9281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00426d2.cif
_cod_data_source_block           r1d-2
_cod_depositor_comments
'Adding full bibliography for 7716091--7716093.cif.'
_cod_database_code               7716092
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C104 H106 Cl2 N14 O14 Zn2 '
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.650(3)
 0.350(3)
2. 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
3. Restrained distances
 Cl2-O1 = Cl2-O4 = Cl2-O5 = Cl2-O6
 1.5 with sigma of 0.02
 C2-O3
 1.22 with sigma of 0.02
 N4-C6
 1.46 with sigma of 0.02
 C2-N4
 1.36 with sigma of 0.02
 N4-C5
 1.45 with sigma of 0.02
 C2-C5
 2.46 with sigma of 0.04
 C2-C6
 2.45 with sigma of 0.04
 Cl2-O1 \\sim Cl2-O4 \\sim Cl2-O5 \\sim Cl2-O6
 with sigma of 0.02
 O1-O5 \\sim O4-O6 \\sim O1-O6 \\sim O4-O5 \\sim O1-O4 \\sim O5-O6
 with sigma of 0.04
 N4-C5 \\sim N4-C6
 with sigma of 0.02
4. Restrained planarity
 C2, O3, N4, C5, C6
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
Cl2 \\sim O1 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C2 \\sim O3 \\sim N4 \\sim C5 \\sim C6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
6. Rigid body (RIGU) restrains
 Cl2, O1, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, O3, N4, C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7.a Ternary CH refined with riding coordinates:
 C00N(H00N)
7.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00Q(H00C,H00D), C00U(H00H,H00J), C018(H01A,H01B), C01A(H01C,
 H01D), C01B(H01E,H01F), C01C(H01G,H01H), C01L(H01P,H01Q), C01T(H01Y,H)
7.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00S(H00S), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015),
 C019(H019), C01D(H01I), C01E(H01J), C01G(H01K), C01H(H01L), C01I(H01M),
 C01J(H01N), C01K(H01O), C01M(H01R), C01P(H01V), C01Q(H01W), C01R(H01X), C2(H2)
7.d Idealised Me refined as rotating group:
 C00T(H00E,H00F,H00G), C01N(H01S,H01T,H01U), C01U(H01Z,HA,HB), C5(H5A,H5B,H5C),
  C6(H6A,H6B,H6C)
;
_shelx_res_checksum              63298
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.759