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_7714930
_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 H13 Cu F6 N2 O3, Cl O4'
_chemical_formula_sum            'C23 H13 Cl Cu F6 N2 O7'
_chemical_formula_weight         642.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.658(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5260(4)
_cell_length_b                   16.5988(5)
_cell_length_c                   15.9965(5)
_cell_measurement_reflns_used    3192
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.8210
_cell_measurement_theta_min      3.8940
_cell_volume                     2435.50(15)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_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    -55.00  43.00   1.00   50.00    --   17.77 -38.00 -60.00   98
  2  \w    -55.00  62.00   1.00   50.00    --   17.77 -19.00   0.00  117
  3  \w    -96.00 -34.00   1.00   50.00    --  -19.57 178.00  60.00   62
  4  \w    -88.00 -38.00   1.00   50.00    --  -19.57 -57.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.869
_diffrn_reflns_theta_min         3.310
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82126
_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    1.752
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.081
_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     382
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0427P)^2^+5.3129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3677
_reflns_number_total             5645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03806h2.cif
_cod_data_source_block           20200707-czf-zhq-p-cf3-cuclo4-etoh-bingaaayong
_cod_depositor_comments
'Adding full bibliography for 7714929--7714932.cif.'
_cod_database_code               7714930
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.755
_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. Uiso/Uaniso restraints and constraints
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F4A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F6) = Uanis(F6A)
Uanis(F5) = Uanis(F5A)
Uanis(F4) = Uanis(F4A)
3. Others
 Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
 Sof(F4A)=Sof(F6A)=Sof(F5A)=1-FVAR(2)
 Sof(F5)=Sof(F4)=Sof(F6)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C7(H7), C1(H1), C20(H20), C14(H14), C10(H10), C15(H15),
 C9(H9), C16(H16)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              1924
_shelx_hkl_checksum              44278
_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
;