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_7716093
_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_absolute_configuration unk
_chemical_formula_moiety
'2(C52 H52 Co N7 O3), 2(Cl O4), 2[C3H7NO], 4[CH3OH]'
_chemical_formula_sum            'C114 H134 Cl2 Co2 N16 O20'
_chemical_formula_weight         2237.202
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_Int_Tables_number      7
_audit_creation_date             2024-05-01
_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                90
_cell_angle_beta                 111.999(8)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   13.8983(10)
_cell_length_b                   13.9966(10)
_cell_length_c                   15.2105(10)
_cell_measurement_reflns_used    18408
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8930
_cell_measurement_theta_min      2.0410
_cell_volume                     2743.4(4)
_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  'olex2.refine 1.5 (Bourhis et al., 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 0.9996
_diffrn_measured_fraction_theta_max 0.9509
_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    -10.00  83.00   0.50   11.83    --   10.55  19.00 -60.00  186
  2  \w     -5.00  77.00   0.50   11.83    --   10.55  37.00 120.00  164
  3  \w     -5.00  46.00   0.50   11.83    --   10.55 -99.00 -60.00  102
  4  \w     20.00  71.00   0.50   11.83    --   10.55-140.00 -24.00  102
  5  \w     -5.00  22.00   0.50   11.83    --  -11.09 -99.00-180.00   54
  6  \w    -23.00  18.00   0.50   11.83    --  -11.09 -99.00-150.00   82
  7  \w    -15.00  24.00   0.50   11.83    --  -11.09 -99.00 -30.00   78
  8  \w    -18.00  46.00   0.50   11.83    --   10.55 -99.00  30.00  128
  9  \w     14.00  64.00   0.50   11.83    --   10.55-129.00 148.00  100
 10  \w    -11.00  15.00   0.50   11.83    --  -11.09 -99.00  60.00   52
 11  \w    -19.00  21.00   0.50   11.83    --  -11.09 -99.00 120.00   80
 12  \w    -21.00   4.00   0.50   11.83    --  -11.09 -37.00  60.00   50
 13  \w    -37.00   4.00   0.50   11.83    --  -11.09 -19.00  90.00   82
 14  \w    -23.00  48.00   0.50   11.83    --  -11.09  37.00  60.00  142
 15  \w    -26.00  55.00   0.50   11.83    --  -11.09  37.00 -90.00  162
 16  \w    -46.00  18.00   0.50   11.83    --   10.55 -37.00 -60.00  128
 17  \w    -66.00 -41.00   0.50   11.83    --  -11.09 -37.00  60.00   50
 18  \w    -82.00 -51.00   0.50   11.83    --  -11.09 -19.00  90.00   62
;
_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      0.0039320000
_diffrn_orient_matrix_UB_12      -0.0503946000
_diffrn_orient_matrix_UB_13      -0.0018933000
_diffrn_orient_matrix_UB_21      -0.0221928000
_diffrn_orient_matrix_UB_22      -0.0046588000
_diffrn_orient_matrix_UB_23      0.0348280000
_diffrn_orient_matrix_UB_31      -0.0502837000
_diffrn_orient_matrix_UB_32      -0.0018909000
_diffrn_orient_matrix_UB_33      -0.0362421000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9509
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40566
_diffrn_reflns_point_group_measured_fraction_full 0.9723
_diffrn_reflns_point_group_measured_fraction_max 0.8996
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.38
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80336
_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            pink
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             1179.774
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.5625
_refine_diff_density_min         -0.4737
_refine_diff_density_rms         0.0556
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.078(9)
_refine_ls_d_res_high            0.7727
_refine_ls_d_res_low             9.9345
_refine_ls_goodness_of_fit_ref   0.9623
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    102
_refine_ls_number_parameters     619
_refine_ls_number_reflns         11191
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.9622
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          -0.0050
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.848
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                7065
_reflns_number_total             11191
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4dt00426d2.cif
_cod_data_source_block           R1E
_cod_depositor_comments
'Adding full bibliography for 7716091--7716093.cif.'
_cod_original_sg_symbol_Hall     ' P -2yac'
_cod_database_code               7716093
_chemical_oxdiff_formula         'C88 H94 Co2 N22 O12 Cl1 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C020-N00E
 1.64 with sigma of 0.02
 C01Y-C020
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C01T) = Uanis(C01N) = Uanis(C1) = Uanis(C016) = Uanis(C00Z)
4. Others
 Fixed Sof: O00X(0.85) H(0.15) Ha(0.15) H01x(0.85) H01y(0.85) Hb(0.15)
 Hc(0.15) H01z(0.85) Hd(0.85) C01Y(0.65) H01(0.65) He(0.65) C020(0.65)
 H02a(0.65) H02b(0.65) C3(0.35) H3a(0.35) H3b(0.35) C2(0.35) H2a(0.35)
 H2b(0.35) O9(0.15)
5.a Ternary CH refined with riding coordinates:
 C00S(H00S)
5.b Secondary CH2 refined with riding coordinates:
 C010(H01a,H01b), C01G(H01k,H01l), C01K(H01n,H01o), C01L(H01p,H01q), C01S(H01u,
 H01v), C01U(H,Ha), C01U(H01x,H01y), C01X(Hb,Hc), C01X(H01z,Hd), C01Y(H01,He),
 C020(H02a,H02b), C3(H3a,H3b), C2(H2a,H2b)
5.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01f), C01B(H01g), C01C(H01h), C01D(H01i),
 C01F(H01j), C01J(H01m), C01M(H01r), C01N(H01s), C01O(H01t), C01T(H01w)
5.d Idealised Me refined as rotating group:
 C00U(H00a,H00b,H00c), C015(H01c,H01d,H01e), C01Z(H1,Hf,Hg)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.741