#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:20:49 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290194 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/49/7714929.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7714929
loop_
_publ_author_name
'Zhang, Hai-Qun'
'Lu, Xing'
'Wu, Jiang-Lun'
'Ou, Mei-Quan'
'Chen, Nan-Feng'
'Liang, Hong'
'Chen, Zhen-Feng'
_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 H15 Cu N2 O3, Cl O4'
_chemical_formula_sum            'C21 H15 Cl Cu N2 O7'
_chemical_formula_weight         506.34
_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   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                112.775(6)
_cell_angle_beta                 107.363(5)
_cell_angle_gamma                93.359(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2985(5)
_cell_length_b                   10.3543(7)
_cell_length_c                   11.9616(7)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.1010
_cell_measurement_theta_min      3.8040
_cell_volume                     993.44(12)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.416
_exptl_absorpt_coefficient_mu    1.284
_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    1.693
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0527
_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/[σ²(Fo²)+(0.0605P)²+1.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2972
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03806h2.cif
_cod_data_source_block           20191030-czf-zhq-p-p-cuclo4-meoh-chcnaaayong_pl
_cod_depositor_comments
'Adding full bibliography for 7714929--7714932.cif.'
_cod_original_cell_volume        993.44(11)
_cod_database_code               7714929
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.723
_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.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C18(H18), C10(H10), C12(H12), C1(H1), C4(H4), C7(H7),
 C9(H9), C3(H3), C2(H2), C8(H8)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.10896(5) 0.37900(5) 0.04192(5) 0.03606(19) Uani 1 1 d . . . . .
O1 O 1.0862(3) 0.4437(3) -0.0897(3) 0.0387(7) Uani 1 1 d . . . . .
O2 O 1.2892(3) 0.5253(3) 0.1568(3) 0.0384(7) Uani 1 1 d . . . . .
O3 O 1.7083(3) 0.7892(4) 0.0541(3) 0.0555(9) Uani 1 1 d . . . . .
N2 N 1.1121(4) 0.3076(4) 0.1741(3) 0.0348(8) Uani 1 1 d . . . . .
N1 N 0.9318(3) 0.2167(4) -0.0654(3) 0.0333(8) Uani 1 1 d . . . . .
C20 C 1.3389(4) 0.5881(4) -0.0019(4) 0.0310(8) Uani 1 1 d . . . . .
C11 C 1.1975(4) 0.5148(4) -0.1015(4) 0.0319(9) Uani 1 1 d . . . . .
C19 C 1.3746(4) 0.5952(4) 0.1265(4) 0.0330(9) Uani 1 1 d . . . . .
C14 C 1.4224(5) 0.6636(5) -0.1445(5) 0.0433(11) Uani 1 1 d . . . . .
H14 H 1.496976 0.711389 -0.159718 0.052 Uiso 1 1 calc R U . . .
C16 C 1.6040(5) 0.7390(4) 0.0787(5) 0.0408(10) Uani 1 1 d . . . . .
C6 C 0.9938(4) 0.2004(4) 0.1370(4) 0.0358(9) Uani 1 1 d . . . . .
C15 C 1.4514(4) 0.6635(4) -0.0253(4) 0.0363(9) Uani 1 1 d . . . . .
C13 C 1.2810(5) 0.5921(5) -0.2431(5) 0.0445(11) Uani 1 1 d . . . . .
H13 H 1.261782 0.593801 -0.323415 0.053 Uiso 1 1 calc R U . . .
C18 C 1.5159(4) 0.6847(5) 0.2294(4) 0.0389(10) Uani 1 1 d . . . . .
H18 H 1.530015 0.696158 0.313262 0.047 Uiso 1 1 calc R U . . .
C10 C 1.2105(5) 0.3629(5) 0.2960(4) 0.0479(11) Uani 1 1 d . . . . .
H10 H 1.292726 0.436107 0.321650 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8924(4) 0.1483(4) 0.0005(4) 0.0352(9) Uani 1 1 d . . . . .
C17 C 1.6269(4) 0.7518(5) 0.2093(4) 0.0400(10) Uani 1 1 d . . . . .
C12 C 1.1703(5) 0.5194(5) -0.2229(4) 0.0394(10) Uani 1 1 d . . . . .
H12 H 1.076508 0.472879 -0.289398 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8479(5) 0.1758(5) -0.1896(4) 0.0407(10) Uani 1 1 d . . . . .
H1 H 0.876232 0.222491 -0.234705 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7665(5) 0.0353(5) -0.0606(5) 0.0473(11) Uani 1 1 d . . . . .
H4 H 0.741376 -0.013248 -0.015778 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9692(5) 0.1493(5) 0.2215(5) 0.0495(12) Uani 1 1 d . . . . .
H7 H 0.886124 0.076288 0.194117 0.059 Uiso 1 1 calc R U . . .
C9 C 1.1941(6) 0.3154(6) 0.3843(5) 0.0594(13) Uani 1 1 d . . . . .
H9 H 1.265315 0.354387 0.468031 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6804(5) -0.0032(5) -0.1874(5) 0.0548(13) Uani 1 1 d . . . . .
H3 H 0.594511 -0.076808 -0.228979 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7212(5) 0.0671(5) -0.2530(5) 0.0499(11) Uani 1 1 d . . . . .
H2 H 0.663687 0.041491 -0.339390 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0700(6) 0.2084(6) 0.3475(5) 0.0625(14) Uani 1 1 d . . . . .
H8 H 1.054933 0.177002 0.407010 0.075 Uiso 1 1 calc R U . . .
C21 C 1.7764(5) 0.8368(5) 0.3145(5) 0.0546(13) Uani 1 1 d . . . . .
H21A H 1.773064 0.843102 0.395869 0.082 Uiso 1 1 calc R U . . .
H21B H 1.793264 0.931084 0.318516 0.082 Uiso 1 1 calc R U . . .
H21C H 1.858660 0.790600 0.296475 0.082 Uiso 1 1 calc R U . . .
Cl1 Cl 0.68825(16) 0.22908(15) 0.46909(13) 0.0638(4) Uani 1 1 d . . . . .
O4 O 0.6899(5) 0.1569(4) 0.3421(4) 0.0731(11) Uani 1 1 d . . . . .
O6 O 0.6055(7) 0.1359(7) 0.4966(5) 0.140(2) Uani 1 1 d . . . . .
O7 O 0.5939(7) 0.3350(6) 0.4668(6) 0.131(2) Uani 1 1 d . . . . .
O5 O 0.8279(6) 0.2917(9) 0.5567(6) 0.179(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 91.72(11) . . ?
O1 Cu1 N2 174.82(12) . . ?
O1 Cu1 N1 93.94(12) . . ?
O2 Cu1 N2 92.47(12) . . ?
O2 Cu1 N1 173.85(12) . . ?
N2 Cu1 N1 82.01(13) . . ?
C11 O1 Cu1 125.1(2) . . ?
C19 O2 Cu1 127.2(3) . . ?
C6 N2 Cu1 114.6(3) . . ?
C10 N2 Cu1 126.3(3) . . ?
C10 N2 C6 118.8(4) . . ?
C5 N1 Cu1 113.9(3) . . ?
C1 N1 Cu1 126.7(3) . . ?
C1 N1 C5 119.4(3) . . ?
C11 C20 C19 122.7(3) . . ?
C11 C20 C15 119.6(4) . . ?
C15 C20 C19 117.6(4) . . ?
O1 C11 C20 124.4(4) . . ?
O1 C11 C12 116.9(4) . . ?
C20 C11 C12 118.6(3) . . ?
O2 C19 C20 123.5(4) . . ?
O2 C19 C18 116.1(4) . . ?
C20 C19 C18 120.4(3) . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
O3 C16 C15 120.3(4) . . ?
O3 C16 C17 121.0(4) . . ?
C17 C16 C15 118.7(3) . . ?
N2 C6 C5 113.9(3) . . ?
N2 C6 C7 122.1(4) . . ?
C7 C6 C5 124.0(4) . . ?
C20 C15 C16 120.2(4) . . ?
C14 C15 C20 120.3(4) . . ?
C14 C15 C16 119.5(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C19 C18 H18 118.4 . . ?
C17 C18 C19 123.2(4) . . ?
C17 C18 H18 118.4 . . ?
N2 C10 H10 119.0 . . ?
N2 C10 C9 122.1(4) . . ?
C9 C10 H10 119.0 . . ?
N1 C5 C6 115.1(3) . . ?
N1 C5 C4 120.6(4) . . ?
C4 C5 C6 124.3(4) . . ?
C16 C17 C21 118.0(4) . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 C21 122.9(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.0(4) . . ?
C2 C1 H1 119.0 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(4) . . ?
C8 C7 H7 120.6 . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 Cl1 O7 106.8(3) . . ?
O6 Cl1 O4 109.1(3) . . ?
O6 Cl1 O7 103.3(4) . . ?
O5 Cl1 O4 112.9(3) . . ?
O5 Cl1 O6 114.1(5) . . ?
O5 Cl1 O7 110.0(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.899(3) . ?
Cu1 O2 1.925(3) . ?
Cu1 N2 1.982(3) . ?
Cu1 N1 1.982(3) . ?
O1 C11 1.308(4) . ?
O2 C19 1.262(4) . ?
O3 C16 1.236(5) . ?
N2 C6 1.350(5) . ?
N2 C10 1.337(5) . ?
N1 C5 1.353(5) . ?
N1 C1 1.334(5) . ?
C20 C11 1.404(5) . ?
C20 C19 1.443(5) . ?
C20 C15 1.425(5) . ?
C11 C12 1.419(5) . ?
C19 C18 1.452(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(6) . ?
C14 C13 1.397(6) . ?
C16 C15 1.496(6) . ?
C16 C17 1.463(6) . ?
C6 C5 1.478(6) . ?
C6 C7 1.376(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.373(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.341(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.368(6) . ?
C5 C4 1.393(6) . ?
C17 C21 1.499(6) . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.371(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.370(6) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl1 O4 1.415(4) . ?
Cl1 O6 1.393(5) . ?
Cl1 O7 1.448(5) . ?
Cl1 O5 1.329(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C11 C20 -18.6(5) . . . . ?
Cu1 O1 C11 C12 162.8(3) . . . . ?
Cu1 O2 C19 C20 8.0(5) . . . . ?
Cu1 O2 C19 C18 -171.3(3) . . . . ?
Cu1 N2 C6 C5 5.3(4) . . . . ?
Cu1 N2 C6 C7 -172.7(3) . . . . ?
Cu1 N2 C10 C9 173.1(4) . . . . ?
Cu1 N1 C5 C6 -3.7(4) . . . . ?
Cu1 N1 C5 C4 177.6(3) . . . . ?
Cu1 N1 C1 C2 -175.8(3) . . . . ?
O1 C11 C12 C13 179.8(4) . . . . ?
O2 Cu1 O1 C11 24.7(3) . . . . ?
O2 C19 C18 C17 171.7(4) . . . . ?
O3 C16 C15 C20 171.0(4) . . . . ?
O3 C16 C15 C14 -7.0(6) . . . . ?
O3 C16 C17 C18 -174.0(4) . . . . ?
O3 C16 C17 C21 4.4(6) . . . . ?
N2 C6 C5 N1 -1.0(5) . . . . ?
N2 C6 C5 C4 177.6(4) . . . . ?
N2 C6 C7 C8 -0.9(7) . . . . ?
N2 C10 C9 C8 -1.3(8) . . . . ?
N1 Cu1 O1 C11 -152.9(3) . . . . ?
N1 C5 C4 C3 -1.8(6) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
C20 C11 C12 C13 1.1(6) . . . . ?
C20 C19 C18 C17 -7.6(6) . . . . ?
C11 C20 C19 O2 7.2(6) . . . . ?
C11 C20 C19 C18 -173.5(4) . . . . ?
C11 C20 C15 C14 -0.5(6) . . . . ?
C11 C20 C15 C16 -178.5(4) . . . . ?
C19 C20 C11 O1 -1.6(6) . . . . ?
C19 C20 C11 C12 177.1(4) . . . . ?
C19 C20 C15 C14 -178.4(4) . . . . ?
C19 C20 C15 C16 3.7(6) . . . . ?
C19 C18 C17 C16 2.2(6) . . . . ?
C19 C18 C17 C21 -176.2(4) . . . . ?
C14 C13 C12 C11 -0.4(7) . . . . ?
C6 N2 C10 C9 -0.7(7) . . . . ?
C6 C5 C4 C3 179.7(4) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C15 C20 C11 O1 -179.3(4) . . . . ?
C15 C20 C11 C12 -0.7(6) . . . . ?
C15 C20 C19 O2 -175.0(4) . . . . ?
C15 C20 C19 C18 4.3(5) . . . . ?
C15 C14 C13 C12 -0.8(7) . . . . ?
C15 C16 C17 C18 5.9(6) . . . . ?
C15 C16 C17 C21 -175.7(4) . . . . ?
C13 C14 C15 C20 1.3(6) . . . . ?
C13 C14 C15 C16 179.2(4) . . . . ?
C10 N2 C6 C5 179.8(4) . . . . ?
C10 N2 C6 C7 1.8(6) . . . . ?
C10 C9 C8 C7 2.2(8) . . . . ?
C5 N1 C1 C2 0.8(6) . . . . ?
C5 C6 C7 C8 -178.6(4) . . . . ?
C5 C4 C3 C2 1.6(7) . . . . ?
C17 C16 C15 C20 -8.9(6) . . . . ?
C17 C16 C15 C14 173.1(4) . . . . ?
C1 N1 C5 C6 179.2(3) . . . . ?
C1 N1 C5 C4 0.6(6) . . . . ?
C4 C3 C2 C1 -0.3(7) . . . . ?
C7 C6 C5 N1 176.9(4) . . . . ?
C7 C6 C5 C4 -4.5(7) . . . . ?
