Potent EGFR/PARP-1 inhibition by spirooxindole-triazole hybrids for targeted liver cancer therapy.
Nafie, Mohamed S.; Ali, M.; Alwehaibi, Moayad Abdullah; Alayyaf, Abdulmajeed Abdullah; Al-Muhanna, Muhanna K; Almuqati, Naif S.; Alghamdi, Abdullah A.; Haukka, Matti; Tariq, Syeda Sumayya; Ul-Haq, Zaheer; Barakat, Assem; RSC advances 15 (2025) 58–74; doi:10.1039/d4ra05966b

data_7249744
_publ_section_title
;
 Potent EGFR/PARP-1 inhibition by spirooxindole-triazole hybrids for
 targeted liver cancer therapy.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              58
_journal_page_last               74
_journal_paper_doi               10.1039/d4ra05966b
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C20 H12 Cl3 N3 O2'
_chemical_formula_sum            'C20 H12 Cl3 N3 O2'
_chemical_formula_weight         432.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.742(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.66680(10)
_cell_length_b                   13.8977(2)
_cell_length_c                   9.5441(2)
_cell_measurement_reflns_used    8893
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      36.2310
_cell_measurement_theta_min      2.7100
_cell_volume                     944.59(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2022)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\f scans and \w scans with \k offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19035
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.323
_diffrn_reflns_theta_min         2.297
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         9361
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0350P)^2^+0.0239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                8190
_reflns_number_total             9361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05966b2.cif
_cod_data_source_block           ab1417_pr
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249744
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              15987