Palladium mediated C-O bond activation of benzopyrone in 4-oxo-4H-chromone-3-carbaldehyde-4(N)-substituted thiosemicarbazone: Synthesis, structure, nucleic acid/albumin interaction, DNA cleavage, antioxidant and cytotoxic studies
Arumugam, Shanmugapriya; Giriraj, Kalaiarasi; Manoharan, Ravi; Sparkes, Hazel Anne; Palaniappan, Kalaivani; Prabhakaran, Rathinasabapathi; New Journal of Chemistry 45 (2021) 20227–20240; doi:10.1039/D1NJ04076F

data_7060988
_publ_section_title
;
 Palladium mediated C-O bond activation of benzopyrone in
 4-oxo-4H-chromone-3-carbaldehyde-4(N)-substituted thiosemicarbazone:
 Synthesis, structure, nucleic acid/albumin interaction, DNA cleavage,
 antioxidant and cytotoxic studies
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20227
_journal_page_last               20240
_journal_paper_doi               10.1039/D1NJ04076F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C31 H27 Cl N3 O2 P Pd S'
_chemical_formula_sum            'C31 H27 Cl N3 O2 P Pd S'
_chemical_formula_weight         678.43
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-10-15 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                83.771(3)
_cell_angle_beta                 83.572(3)
_cell_angle_gamma                68.836(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2795(6)
_cell_length_b                   11.5534(6)
_cell_length_c                   11.9252(7)
_cell_measurement_reflns_used    7096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.18
_cell_volume                     1436.23(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26615
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.940
_diffrn_reflns_theta_min         1.723
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0704 before and 0.0456 after correction. The Ratio of minimum to maximum transmission is 0.8023. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0237P)^2^+0.6878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5792
_reflns_number_total             6865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04076f2.cif
_cod_data_source_block           testt1
_cod_database_code               7060988
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.739
_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
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              86534
_olex2_submission_special_instructions 'No special instructions were received'