Discovery of mitochondrion-targeting copper(II)-plumbagin and -bipyridine complexes as chemodynamic therapy agents with enhanced antitumor activity.
Zhang, Hai-Qun; Lu, Xing; Wu, Jiang-Lun; Ou, Mei-Quan; Chen, Nan-Feng; Liang, Hong; Chen, Zhen-Feng; Dalton transactions (Cambridge, England : 2003) 53 (2024) 3244–3253; doi:10.1039/d3dt03806h

data_7714931
_publ_section_title
;
 Discovery of mitochondrion-targeting copper(II)-plumbagin and -bipyridine
 complexes as chemodynamic therapy agents with enhanced antitumor
 activity.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3244
_journal_page_last               3253
_journal_paper_doi               10.1039/d3dt03806h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C23 H19 Cu N2 O3, Cl O4'
_chemical_formula_sum            'C23 H19 Cl Cu N2 O7'
_chemical_formula_weight         534.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1043(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3791(2)
_cell_length_b                   10.6291(2)
_cell_length_c                   22.1108(4)
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.3460
_cell_measurement_theta_min      3.4450
_cell_volume                     2202.77(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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     34.00  94.00   1.00    5.00    --   17.93-178.00   0.00   60
  2  \w    -20.00  60.00   1.00    5.00    --   17.93 -99.00 -30.00   80
  3  \w     -3.00  87.00   1.00    5.00    --   17.93  57.00 -90.00   90
  4  \w    -52.00  49.00   1.00    5.00    --  -19.72  19.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648891000
_diffrn_orient_matrix_UB_12      0.0230110000
_diffrn_orient_matrix_UB_13      -0.0132235000
_diffrn_orient_matrix_UB_21      -0.0152905000
_diffrn_orient_matrix_UB_22      -0.0605557000
_diffrn_orient_matrix_UB_23      -0.0120945000
_diffrn_orient_matrix_UB_31      -0.0358088000
_diffrn_orient_matrix_UB_32      -0.0160664000
_diffrn_orient_matrix_UB_33      0.0266279000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13491
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.455
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0458P)^2^+1.4824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3842
_reflns_number_total             4498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03806h2.cif
_cod_data_source_block           20190911-p-4-cuclo4aaa
_cod_depositor_comments
'Adding full bibliography for 7714929--7714932.cif.'
_cod_original_cell_volume        2202.78(8)
_cod_database_code               7714931
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.737
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O7)=Sof(O4)=Sof(O9)=Sof(O5)=1-FVAR(1)
 Sof(O8)=Sof(O6)=Sof(O10)=Sof(O11)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C21(H21)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_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 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.677