#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/26/7022651.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_7022651
loop_
_publ_author_name
'Berthet, Nathalie'
'Martel-Frachet, Véronique'
'Michel, Fabien'
'Philouze, Christian'
'Hamman, Sylvain'
'Ronot, Xavier'
'Thomas, Fabrice'
_publ_section_title
;
 Nuclease and anti-proliferative activities of copper(II) complexes of N3O
 tripodal ligands involving a sterically hindered phenolate.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8468
_journal_page_last               8483
_journal_paper_doi               10.1039/c3dt32659d
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C40 H40 Cu2 N6 O4, 2(Cl O4), 4(C2 H3 N)'
_chemical_formula_sum            'C48 H52 Cl2 Cu2 N10 O12'
_chemical_formula_weight         1158.98
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-09
_audit_creation_method
;
Olex2 1.1
(compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.731(2)
_cell_length_b                   19.464(4)
_cell_length_c                   10.997(2)
_cell_measurement_temperature    150
_cell_volume                     2506.8(8)
_computing_cell_refinement       'Bruker Enraf Nonius kappa CCD'
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30584
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         34.99
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Mo
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.850967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0501 before and 0.0342 after correction.
The Ratio of minimum to maximum transmission is 0.8510.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         10407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0537P)²+1.4671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                7267
_reflns_number_total             10407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt32659d.txt
_cod_data_source_block           sad2_Fab14
_cod_original_cell_volume        2506.6(9)
_cod_database_code               7022651
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.628929(18) -0.011781(11) 0.49960(2) 0.01242(6) Uani 1 1 d .
Cl1 Cl 0.04194(5) 0.18292(3) 0.07963(5) 0.02488(10) Uani 1 1 d .
O1 O 0.47905(11) -0.05855(7) 0.55744(13) 0.0151(2) Uani 1 1 d .
O2 O 0.48642(14) -0.22848(9) 0.96223(14) 0.0231(3) Uani 1 1 d .
O3 O -0.08063(17) 0.19095(12) 0.0761(2) 0.0397(4) Uani 1 1 d .
O4 O 0.0688(2) 0.11229(11) 0.0601(2) 0.0461(5) Uani 1 1 d .
O5 O 0.0884(2) 0.22478(15) -0.0127(3) 0.0564(7) Uani 1 1 d .
O6 O 0.0906(2) 0.20267(12) 0.1980(2) 0.0451(5) Uani 1 1 d .
N1 N 0.73175(13) -0.08659(8) 0.57239(14) 0.0142(3) Uani 1 1 d .
N2 N 0.65081(13) -0.06415(8) 0.34385(15) 0.0160(3) Uani 1 1 d .
N3 N 0.71619(14) 0.04885(9) 0.61863(15) 0.0177(3) Uani 1 1 d .
N4 N 0.9096(2) 0.04983(14) 0.3815(3) 0.0414(6) Uani 1 1 d .
N5 N 0.6482(2) 0.02108(18) -0.0838(2) 0.0453(6) Uani 1 1 d .
C1 C 0.47835(14) -0.09962(9) 0.65548(16) 0.0135(3) Uani 1 1 d .
C2 C 0.38440(15) -0.10261(10) 0.72795(17) 0.0159(3) Uani 1 1 d .
H2 H 0.3196 -0.0748 0.7073 0.019 Uiso 1 1 calc R
C3 C 0.38304(16) -0.14537(10) 0.82991(18) 0.0174(3) Uani 1 1 d .
H3 H 0.3176 -0.1470 0.8768 0.021 Uiso 1 1 calc R
C4 C 0.47829(17) -0.18555(10) 0.86234(17) 0.0172(3) Uani 1 1 d .
C5 C 0.57242(16) -0.18403(10) 0.78970(17) 0.0165(3) Uani 1 1 d .
H5 H 0.6372 -0.2116 0.8114 0.020 Uiso 1 1 calc R
C6 C 0.57285(15) -0.14275(9) 0.68592(16) 0.0142(3) Uani 1 1 d .
C7 C 0.66785(15) -0.15089(10) 0.59990(17) 0.0159(3) Uani 1 1 d .
H7A H 0.7231 -0.1850 0.6351 0.019 Uiso 1 1 calc R
H7B H 0.6349 -0.1700 0.5222 0.019 Uiso 1 1 calc R
C8 C 0.3959(2) -0.22396(12) 1.0436(2) 0.0248(4) Uani 1 1 d .
H8A H 0.3239 -0.2376 1.0008 0.037 Uiso 1 1 calc R
H8B H 0.3897 -0.1766 1.0727 0.037 Uiso 1 1 calc R
H8C H 0.4121 -0.2546 1.1132 0.037 Uiso 1 1 calc R
C9 C 0.58356(17) -0.06353(10) 0.24005(18) 0.0191(3) Uani 1 1 d .
H9 H 0.5183 -0.0345 0.2347 0.023 Uiso 1 1 calc R
C10 C 0.6073(2) -0.10421(12) 0.1409(2) 0.0239(4) Uani 1 1 d .
H10 H 0.5597 -0.1027 0.0681 0.029 Uiso 1 1 calc R
C11 C 0.7017(2) -0.14711(12) 0.1502(2) 0.0270(4) Uani 1 1 d .
H11 H 0.7197 -0.1752 0.0833 0.032 Uiso 1 1 calc R
C12 C 0.77006(19) -0.14876(11) 0.2579(2) 0.0232(4) Uani 1 1 d .
H12 H 0.8345 -0.1783 0.2660 0.028 Uiso 1 1 calc R
C13 C 0.74227(16) -0.10629(10) 0.35351(18) 0.0177(3) Uani 1 1 d .
C14 C 0.81057(16) -0.10200(11) 0.47405(18) 0.0185(3) Uani 1 1 d .
H14A H 0.8503 -0.1461 0.4913 0.022 Uiso 1 1 calc R
H14B H 0.8688 -0.0654 0.4707 0.022 Uiso 1 1 calc R
C15 C 0.7082(2) 0.11763(11) 0.6244(2) 0.0249(4) Uani 1 1 d .
H15 H 0.6466 0.1400 0.5808 0.030 Uiso 1 1 calc R
C16 C 0.7874(3) 0.15695(13) 0.6922(2) 0.0339(5) Uani 1 1 d .
H16 H 0.7793 0.2054 0.6966 0.041 Uiso 1 1 calc R
C17 C 0.8790(2) 0.12406(15) 0.7539(2) 0.0331(5) Uani 1 1 d .
H17 H 0.9356 0.1500 0.7989 0.040 Uiso 1 1 calc R
C18 C 0.88689(19) 0.05308(13) 0.7489(2) 0.0258(4) Uani 1 1 d .
H18 H 0.9487 0.0297 0.7903 0.031 Uiso 1 1 calc R
C19 C 0.80256(16) 0.01680(11) 0.68196(17) 0.0177(3) Uani 1 1 d .
C20 C 0.79571(16) -0.06044(11) 0.68339(18) 0.0187(3) Uani 1 1 d .
H20A H 0.8738 -0.0799 0.6880 0.022 Uiso 1 1 calc R
H20B H 0.7572 -0.0756 0.7565 0.022 Uiso 1 1 calc R
C21 C 0.89735(19) 0.10792(14) 0.3814(2) 0.0274(4) Uani 1 1 d .
C22 C 0.8796(2) 0.18170(14) 0.3783(3) 0.0360(5) Uani 1 1 d .
H22A H 0.9238 0.2020 0.3145 0.054 Uiso 1 1 calc R
H22B H 0.9046 0.2015 0.4574 0.054 Uiso 1 1 calc R
H22C H 0.7983 0.1915 0.3611 0.054 Uiso 1 1 calc R
C23 C 0.7255(2) 0.01956(13) -0.0155(2) 0.0290(4) Uani 1 1 d .
C24 C 0.8241(2) 0.01720(14) 0.0701(2) 0.0319(5) Uani 1 1 d .
H24A H 0.8717 -0.0224 0.0516 0.048 Uiso 1 1 calc R
H24B H 0.7987 0.0129 0.1531 0.048 Uiso 1 1 calc R
H24C H 0.8686 0.0595 0.0634 0.048 Uiso 1 1 calc R
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'
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'
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'
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
O1 Cu1 Cu1 43.09(4) 3_656 3_656
O1 Cu1 Cu1 39.00(4) . 3_656
O1 Cu1 O1 82.09(6) 3_656 .
O1 Cu1 N1 174.54(6) 3_656 .
O1 Cu1 N2 101.17(7) 3_656 .
O1 Cu1 N3 95.45(7) 3_656 .
N1 Cu1 Cu1 132.27(5) . 3_656
N1 Cu1 O1 93.34(6) . .
N2 Cu1 Cu1 104.59(5) . 3_656
N2 Cu1 O1 100.76(7) . .
N2 Cu1 N1 82.56(7) . .
N3 Cu1 Cu1 112.24(5) . 3_656
N3 Cu1 O1 117.46(7) . .
N3 Cu1 N1 83.97(7) . .
N3 Cu1 N2 140.05(7) . .
O4 Cl1 O3 109.14(15) . .
O4 Cl1 O5 110.10(17) . .
O4 Cl1 O6 108.22(15) . .
O5 Cl1 O3 109.76(14) . .
O5 Cl1 O6 109.91(18) . .
O6 Cl1 O3 109.68(15) . .
Cu1 O1 Cu1 97.91(6) 3_656 .
C1 O1 Cu1 130.11(11) . 3_656
C1 O1 Cu1 122.87(11) . .
C4 O2 C8 116.20(16) . .
C7 N1 Cu1 112.75(11) . .
C14 N1 Cu1 103.75(11) . .
C14 N1 C7 108.44(15) . .
C20 N1 Cu1 109.84(12) . .
C20 N1 C7 110.80(15) . .
C20 N1 C14 111.06(15) . .
C9 N2 Cu1 127.97(13) . .
C9 N2 C13 119.68(17) . .
C13 N2 Cu1 112.26(13) . .
C15 N3 Cu1 125.77(14) . .
C15 N3 C19 119.25(18) . .
C19 N3 Cu1 113.94(14) . .
O1 C1 C2 121.60(15) . .
O1 C1 C6 120.14(15) . .
C2 C1 C6 118.23(16) . .
C1 C2 H2 119.1 . .
C3 C2 C1 121.88(16) . .
C3 C2 H2 119.1 . .
C2 C3 H3 120.2 . .
C4 C3 C2 119.58(17) . .
C4 C3 H3 120.2 . .
O2 C4 C3 124.16(17) . .
O2 C4 C5 116.53(17) . .
C3 C4 C5 119.30(17) . .
C4 C5 H5 119.4 . .
C6 C5 C4 121.25(17) . .
C6 C5 H5 119.4 . .
C1 C6 C7 120.67(16) . .
C5 C6 C1 119.68(16) . .
C5 C6 C7 119.27(16) . .
N1 C7 C6 115.74(15) . .
N1 C7 H7A 108.3 . .
N1 C7 H7B 108.3 . .
C6 C7 H7A 108.3 . .
C6 C7 H7B 108.3 . .
H7A C7 H7B 107.4 . .
O2 C8 H8A 109.5 . .
O2 C8 H8B 109.5 . .
O2 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 H9 119.2 . .
N2 C9 C10 121.67(19) . .
C10 C9 H9 119.2 . .
C9 C10 H10 120.6 . .
C11 C10 C9 118.8(2) . .
C11 C10 H10 120.6 . .
C10 C11 H11 120.2 . .
C10 C11 C12 119.7(2) . .
C12 C11 H11 120.2 . .
C11 C12 H12 120.6 . .
C13 C12 C11 118.7(2) . .
C13 C12 H12 120.6 . .
N2 C13 C12 121.45(19) . .
N2 C13 C14 114.47(17) . .
C12 C13 C14 124.07(18) . .
N1 C14 C13 109.10(15) . .
N1 C14 H14A 109.9 . .
N1 C14 H14B 109.9 . .
C13 C14 H14A 109.9 . .
C13 C14 H14B 109.9 . .
H14A C14 H14B 108.3 . .
N3 C15 H15 119.0 . .
N3 C15 C16 121.9(2) . .
C16 C15 H15 119.0 . .
C15 C16 H16 120.6 . .
C15 C16 C17 118.8(2) . .
C17 C16 H16 120.6 . .
C16 C17 H17 120.3 . .
C18 C17 C16 119.4(2) . .
C18 C17 H17 120.3 . .
C17 C18 H18 120.7 . .
C17 C18 C19 118.7(2) . .
C19 C18 H18 120.7 . .
N3 C19 C18 121.9(2) . .
N3 C19 C20 115.36(17) . .
C18 C19 C20 122.55(18) . .
N1 C20 C19 110.99(15) . .
N1 C20 H20A 109.4 . .
N1 C20 H20B 109.4 . .
C19 C20 H20A 109.4 . .
C19 C20 H20B 109.4 . .
H20A C20 H20B 108.0 . .
N4 C21 C22 178.4(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N5 C23 C24 179.3(3) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cu1 3.0600(7) 3_656
Cu1 O1 2.1104(14) .
Cu1 O1 1.9442(13) 3_656
Cu1 N1 2.0259(16) .
Cu1 N2 2.0222(17) .
Cu1 N3 1.9997(18) .
Cl1 O3 1.445(2) .
Cl1 O4 1.429(2) .
Cl1 O5 1.434(2) .
Cl1 O6 1.443(2) .
O1 Cu1 1.9442(13) 3_656
O1 C1 1.343(2) .
O2 C4 1.379(2) .
O2 C8 1.430(3) .
N1 C7 1.499(2) .
N1 C14 1.493(2) .
N1 C20 1.485(3) .
N2 C9 1.350(3) .
N2 C13 1.350(2) .
N3 C15 1.344(3) .
N3 C19 1.349(3) .
N4 C21 1.140(4) .
N5 C23 1.144(4) .
C1 C2 1.398(2) .
C1 C6 1.415(2) .
C2 H2 0.9500 .
C2 C3 1.397(3) .
C3 H3 0.9500 .
C3 C4 1.393(3) .
C4 C5 1.400(3) .
C5 H5 0.9500 .
C5 C6 1.396(3) .
C6 C7 1.511(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9 0.9500 .
C9 C10 1.389(3) .
C10 H10 0.9500 .
C10 C11 1.386(3) .
C11 H11 0.9500 .
C11 C12 1.392(4) .
C12 H12 0.9500 .
C12 C13 1.391(3) .
C13 C14 1.511(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15 0.9500 .
C15 C16 1.387(3) .
C16 H16 0.9500 .
C16 C17 1.393(4) .
C17 H17 0.9500 .
C17 C18 1.386(4) .
C18 H18 0.9500 .
C18 C19 1.391(3) .
C19 C20 1.506(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.451(4) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.449(4) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139160139
