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_7714932
_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         'C21 H17 Cu N4 O3, Cl O4'
_chemical_formula_sum            'C21 H17 Cl Cu N4 O7'
_chemical_formula_weight         536.38
_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     heavy
_audit_creation_date             2021-03-10
_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                109.072(7)
_cell_angle_beta                 110.542(6)
_cell_angle_gamma                90.238(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4798(5)
_cell_length_b                   10.4607(8)
_cell_length_c                   12.3592(8)
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.8200
_cell_measurement_theta_min      4.1520
_cell_volume                     1074.86(14)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.900
_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    -52.00  48.00   1.00   16.00    --   17.77 -77.00 -30.00  100
  2  \w    -20.00  60.00   1.00   16.00    --   17.77 -99.00-120.00   80
  3  \w     -8.00  90.00   1.00   16.00    --   17.77  38.00-120.00   98
  4  \w    -12.00  88.00   1.00   16.00    --   17.77  77.00  90.00  100
  5  \w    -64.00  53.00   1.00   16.00    --  -19.57  19.00 -90.00  117
  6  \w     -4.00  87.00   1.00   16.00    --   17.77  57.00 -30.00   91
  7  \w    -20.00  56.00   1.00   16.00    --   17.77 -99.00  60.00   76
  8  \w    -51.00  38.00   1.00   16.00    --   17.77 -57.00  90.00   89
;
_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      0.0123784000
_diffrn_orient_matrix_UB_12      0.0722489000
_diffrn_orient_matrix_UB_13      0.0197849000
_diffrn_orient_matrix_UB_21      -0.0497512000
_diffrn_orient_matrix_UB_22      -0.0026192000
_diffrn_orient_matrix_UB_23      -0.0591971000
_diffrn_orient_matrix_UB_31      -0.0622346000
_diffrn_orient_matrix_UB_32      0.0038717000
_diffrn_orient_matrix_UB_33      0.0196585000
_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  0.0872
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.806
_diffrn_reflns_theta_min         3.255
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79401
_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    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0708
_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^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2551
_reflns_number_total             5050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03806h2.cif
_cod_data_source_block           20200709-ccf-zhq-pp-4nh2-cuclo4-meoh-ch3cnaaa
_cod_depositor_comments
'Adding full bibliography for 7714929--7714932.cif.'
_cod_database_code               7714932
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.870
_shelx_estimated_absorpt_t_min   0.739
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1BA(H1BA), C3BA(H3BA), C4BA(H4BA), C5BA(H5BA), C6BA(H6BA), C7BA(H7BA),
 C9BA(H9BA), C7AA(H7AA), C8AA(H8AA), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC)
;
_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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.773