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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/07/7220724.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_7220724
loop_
_publ_author_name
'Wang, Xue'
'Zhao, Keqing'
'Elsegood, Mark Robert James'
'Prior, Timothy J.'
'Liu, Xiaoming'
'Li, Wu'
'Sanz, Sergio'
'Brechin, Euan K.'
'Redshaw, Carl'
_publ_section_title
;
 Mono-and Tetra-nuclear copper complexes bearing bis(imino)phenoxide
 derived ligands: catalytic evaluation for benzene oxidation and ROP of
 epsilon-caprolactone
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08696E
_journal_year                    2015
_chemical_formula_moiety         'C66 H82 Cu N4 O2'
_chemical_formula_sum            'C66 H82 Cu N4 O2'
_chemical_formula_weight         1026.89
_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
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-12-21 deposited with the CCDC.
2015-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5566(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8597(6)
_cell_length_b                   12.1852(8)
_cell_length_c                   24.1112(16)
_cell_measurement_reflns_used    6063
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.38
_cell_volume                     2871.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16148
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.704
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1102
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0528
_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)+(0.0471P)²+0.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3485
_reflns_number_total             5606
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra08696e2.cif
_cod_data_source_block           cr29
_cod_database_code               7220724
_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_min   0.772
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.5000 0.0000 0.01473(15) Uani 1 2 d S . P
N1 N 0.5836(2) 0.5102(2) -0.06974(10) 0.0155(6) Uani 1 1 d . . .
C1 C 0.5533(3) 0.6007(2) -0.10850(12) 0.0156(7) Uani 1 1 d . . .
C2 C 0.6383(3) 0.6920(3) -0.10350(13) 0.0183(7) Uani 1 1 d . . .
C3 C 0.6085(3) 0.7756(3) -0.14294(14) 0.0236(8) Uani 1 1 d . . .
H3 H 0.6652 0.8389 -0.1411 0.028 Uiso 1 1 calc R U .
C4 C 0.4988(3) 0.7681(3) -0.18442(14) 0.0234(8) Uani 1 1 d . . .
H4 H 0.4803 0.8261 -0.2107 0.028 Uiso 1 1 calc R U .
C5 C 0.4153(3) 0.6760(3) -0.18792(13) 0.0224(8) Uani 1 1 d . . .
H5 H 0.3405 0.6713 -0.2170 0.027 Uiso 1 1 calc R U .
C6 C 0.4391(3) 0.5905(2) -0.14965(13) 0.0173(7) Uani 1 1 d . . .
C7 C 0.7578(3) 0.6996(3) -0.05693(15) 0.0259(8) Uani 1 1 d . . .
H7 H 0.7327 0.6560 -0.0247 0.031 Uiso 1 1 calc R U .
C8 C 0.7862(4) 0.8168(3) -0.03618(16) 0.0367(10) Uani 1 1 d . . .
H8A H 0.8182 0.8607 -0.0659 0.055 Uiso 1 1 calc R U .
H8B H 0.8566 0.8159 -0.0035 0.055 Uiso 1 1 calc R U .
H8C H 0.7020 0.8490 -0.0258 0.055 Uiso 1 1 calc R U .
C9 C 0.8886(4) 0.6487(3) -0.07388(18) 0.0411(10) Uani 1 1 d . . .
H9A H 0.8712 0.5721 -0.0849 0.062 Uiso 1 1 calc R U .
H9B H 0.9617 0.6519 -0.0421 0.062 Uiso 1 1 calc R U .
H9C H 0.9166 0.6897 -0.1055 0.062 Uiso 1 1 calc R U .
C10 C 0.3471(3) 0.4912(3) -0.15301(13) 0.0230(7) Uani 1 1 d . . .
H10 H 0.3730 0.4474 -0.1182 0.028 Uiso 1 1 calc R U .
C11 C 0.3733(4) 0.4191(3) -0.20257(15) 0.0347(9) Uani 1 1 d . . .
H11A H 0.3562 0.4617 -0.2373 0.052 Uiso 1 1 calc R U .
H11B H 0.3120 0.3555 -0.2050 0.052 Uiso 1 1 calc R U .
H11C H 0.4686 0.3940 -0.1972 0.052 Uiso 1 1 calc R U .
C12 C 0.1960(3) 0.5207(3) -0.15534(17) 0.0365(10) Uani 1 1 d . . .
H12A H 0.1836 0.5692 -0.1240 0.055 Uiso 1 1 calc R U .
H12B H 0.1424 0.4535 -0.1528 0.055 Uiso 1 1 calc R U .
H12C H 0.1649 0.5581 -0.1907 0.055 Uiso 1 1 calc R U .
C13 C 0.6638(3) 0.4369(2) -0.08654(13) 0.0172(7) Uani 1 1 d . . .
H13 H 0.6901 0.4481 -0.1226 0.021 Uiso 1 1 calc R U .
C14 C 0.7177(3) 0.3412(2) -0.05744(13) 0.0169(7) Uani 1 1 d . . .
C15 C 0.8040(3) 0.2742(3) -0.08489(13) 0.0194(7) Uani 1 1 d . . .
H15 H 0.8215 0.2945 -0.1213 0.023 Uiso 1 1 calc R U .
C16 C 0.8644(3) 0.1803(3) -0.06126(13) 0.0198(7) Uani 1 1 d . . .
C17 C 0.8377(3) 0.1556(2) -0.00739(13) 0.0175(7) Uani 1 1 d . . .
H17 H 0.8782 0.0914 0.0100 0.021 Uiso 1 1 calc R U .
C18 C 0.7555(3) 0.2192(2) 0.02249(12) 0.0148(7) Uani 1 1 d . . .
C19 C 0.6899(3) 0.3147(2) -0.00280(13) 0.0158(7) Uani 1 1 d . . .
O1 O 0.6076(2) 0.37347(17) 0.02392(8) 0.0193(5) Uani 1 1 d . . .
C20 C 0.9506(4) 0.1070(3) -0.09287(14) 0.0315(9) Uani 1 1 d . . .
H20A H 0.8922 0.0713 -0.1237 0.047 Uiso 1 1 calc R U .
H20B H 0.9950 0.0510 -0.0675 0.047 Uiso 1 1 calc R U .
H20C H 1.0205 0.1511 -0.1079 0.047 Uiso 1 1 calc R U .
C21 C 0.7293(3) 0.1818(2) 0.07823(13) 0.0162(7) Uani 1 1 d . . .
H21 H 0.6582 0.2149 0.0954 0.019 Uiso 1 1 calc R U .
N2 N 0.8010(3) 0.1053(2) 0.10368(10) 0.0174(6) Uani 1 1 d . . .
C22 C 0.7679(3) 0.0599(3) 0.15453(13) 0.0181(7) Uani 1 1 d . . .
C23 C 0.6844(3) -0.0342(2) 0.15121(14) 0.0208(8) Uani 1 1 d . . .
C24 C 0.6570(3) -0.0818(3) 0.20099(15) 0.0270(8) Uani 1 1 d . . .
H24 H 0.5984 -0.1439 0.1996 0.032 Uiso 1 1 calc R U .
C25 C 0.7132(4) -0.0410(3) 0.25228(15) 0.0280(8) Uani 1 1 d . . .
H25 H 0.6924 -0.0742 0.2858 0.034 Uiso 1 1 calc R U .
C26 C 0.7999(3) 0.0487(3) 0.25466(14) 0.0247(8) Uani 1 1 d . . .
H26 H 0.8396 0.0754 0.2901 0.030 Uiso 1 1 calc R U .
C27 C 0.8303(3) 0.1007(3) 0.20635(13) 0.0174(7) Uani 1 1 d . . .
C28 C 0.6259(4) -0.0816(3) 0.09491(15) 0.0282(8) Uani 1 1 d . . .
H28 H 0.6853 -0.0562 0.0669 0.034 Uiso 1 1 calc R U .
C29 C 0.6259(4) -0.2069(3) 0.09396(16) 0.0372(10) Uani 1 1 d . . .
H29A H 0.7180 -0.2340 0.1074 0.056 Uiso 1 1 calc R U .
H29B H 0.5985 -0.2326 0.0556 0.056 Uiso 1 1 calc R U .
H29C H 0.5613 -0.2346 0.1182 0.056 Uiso 1 1 calc R U .
C30 C 0.4823(4) -0.0375(3) 0.07656(17) 0.0449(11) Uani 1 1 d . . .
H30A H 0.4221 -0.0585 0.1040 0.067 Uiso 1 1 calc R U .
H30B H 0.4470 -0.0682 0.0399 0.067 Uiso 1 1 calc R U .
H30C H 0.4857 0.0427 0.0739 0.067 Uiso 1 1 calc R U .
C31 C 0.9327(3) 0.1945(3) 0.20843(13) 0.0208(7) Uani 1 1 d . . .
H31 H 0.8973 0.2486 0.1788 0.025 Uiso 1 1 calc R U .
C32 C 1.0685(3) 0.1501(3) 0.19393(15) 0.0329(9) Uani 1 1 d . . .
H32A H 1.1023 0.0928 0.2208 0.049 Uiso 1 1 calc R U .
H32B H 1.1354 0.2099 0.1956 0.049 Uiso 1 1 calc R U .
H32C H 1.0550 0.1192 0.1561 0.049 Uiso 1 1 calc R U .
C33 C 0.9558(4) 0.2553(3) 0.26399(14) 0.0294(9) Uani 1 1 d . . .
H33A H 0.8677 0.2797 0.2742 0.044 Uiso 1 1 calc R U .
H33B H 1.0145 0.3192 0.2605 0.044 Uiso 1 1 calc R U .
H33C H 1.0003 0.2062 0.2931 0.044 Uiso 1 1 calc R U .
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'
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 O1 180.0 . 3_665
O1 Cu1 N1 91.73(9) . .
O1 Cu1 N1 88.27(9) 3_665 .
O1 Cu1 N1 88.27(9) . 3_665
O1 Cu1 N1 91.73(9) 3_665 3_665
N1 Cu1 N1 180.0 . 3_665
C13 N1 C1 113.9(2) . .
C13 N1 Cu1 124.4(2) . .
C1 N1 Cu1 121.55(19) . .
C2 C1 C6 123.4(3) . .
C2 C1 N1 118.8(3) . .
C6 C1 N1 117.8(3) . .
C1 C2 C3 117.0(3) . .
C1 C2 C7 120.9(3) . .
C3 C2 C7 122.1(3) . .
C4 C3 C2 121.4(3) . .
C3 C4 C5 120.1(3) . .
C4 C5 C6 121.2(3) . .
C5 C6 C1 116.9(3) . .
C5 C6 C10 121.1(3) . .
C1 C6 C10 122.0(3) . .
C2 C7 C8 113.0(3) . .
C2 C7 C9 112.1(3) . .
C8 C7 C9 109.9(3) . .
C6 C10 C12 113.0(3) . .
C6 C10 C11 109.9(3) . .
C12 C10 C11 111.7(3) . .
N1 C13 C14 127.9(3) . .
C15 C14 C19 120.6(3) . .
C15 C14 C13 116.9(3) . .
C19 C14 C13 122.5(3) . .
C16 C15 C14 122.8(3) . .
C15 C16 C17 116.2(3) . .
C15 C16 C20 121.6(3) . .
C17 C16 C20 122.2(3) . .
C18 C17 C16 123.9(3) . .
C17 C18 C19 119.7(3) . .
C17 C18 C21 119.0(3) . .
C19 C18 C21 121.2(3) . .
O1 C19 C14 122.7(3) . .
O1 C19 C18 120.6(3) . .
C14 C19 C18 116.7(3) . .
C19 O1 Cu1 130.10(19) . .
N2 C21 C18 120.8(3) . .
C21 N2 C22 121.5(3) . .
C23 C22 C27 121.5(3) . .
C23 C22 N2 117.8(3) . .
C27 C22 N2 120.3(3) . .
C24 C23 C22 118.0(3) . .
C24 C23 C28 121.3(3) . .
C22 C23 C28 120.8(3) . .
C25 C24 C23 121.5(3) . .
C24 C25 C26 119.7(3) . .
C25 C26 C27 121.6(3) . .
C26 C27 C22 117.6(3) . .
C26 C27 C31 122.0(3) . .
C22 C27 C31 120.3(3) . .
C23 C28 C30 110.7(3) . .
C23 C28 C29 113.2(3) . .
C30 C28 C29 110.5(3) . .
C27 C31 C33 114.6(3) . .
C27 C31 C32 108.9(3) . .
C33 C31 C32 109.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.917(2) .
Cu1 O1 1.917(2) 3_665
Cu1 N1 1.971(2) .
Cu1 N1 1.971(2) 3_665
N1 C13 1.293(4) .
N1 C1 1.451(4) .
C1 C2 1.388(4) .
C1 C6 1.405(4) .
C2 C3 1.398(4) .
C2 C7 1.519(4) .
C3 C4 1.376(5) .
C4 C5 1.388(4) .
C5 C6 1.391(4) .
C6 C10 1.508(4) .
C7 C8 1.526(5) .
C7 C9 1.535(5) .
C10 C12 1.526(4) .
C10 C11 1.533(4) .
C13 C14 1.427(4) .
C14 C15 1.406(4) .
C14 C19 1.417(4) .
C15 C16 1.378(4) .
C16 C17 1.392(4) .
C16 C20 1.507(4) .
C17 C18 1.389(4) .
C18 C19 1.429(4) .
C18 C21 1.474(4) .
C19 O1 1.313(3) .
C21 N2 1.277(4) .
N2 C22 1.422(4) .
C22 C23 1.408(4) .
C22 C27 1.409(4) .
C23 C24 1.391(4) .
C23 C28 1.518(5) .
C24 C25 1.380(5) .
C25 C26 1.384(5) .
C26 C27 1.393(4) .
C27 C31 1.521(4) .
C28 C30 1.524(5) .
C28 C29 1.527(5) .
C31 C33 1.522(4) .
C31 C32 1.527(4) .
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
C13 N1 C1 C2 -89.8(3)
Cu1 N1 C1 C2 93.0(3)
C13 N1 C1 C6 89.7(3)
Cu1 N1 C1 C6 -87.5(3)
C6 C1 C2 C3 -1.8(5)
N1 C1 C2 C3 177.7(3)
C6 C1 C2 C7 178.1(3)
N1 C1 C2 C7 -2.5(4)
C1 C2 C3 C4 0.8(5)
C7 C2 C3 C4 -179.1(3)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 C6 0.7(5)
C4 C5 C6 C1 -1.6(4)
C4 C5 C6 C10 179.1(3)
C2 C1 C6 C5 2.2(5)
N1 C1 C6 C5 -177.2(3)
C2 C1 C6 C10 -178.6(3)
N1 C1 C6 C10 2.0(4)
C1 C2 C7 C8 -146.6(3)
C3 C2 C7 C8 33.2(4)
C1 C2 C7 C9 88.5(4)
C3 C2 C7 C9 -91.7(4)
C5 C6 C10 C12 -52.3(4)
C1 C6 C10 C12 128.5(3)
C5 C6 C10 C11 73.2(4)
C1 C6 C10 C11 -106.0(3)
C1 N1 C13 C14 177.0(3)
Cu1 N1 C13 C14 -6.0(5)
N1 C13 C14 C15 -179.7(3)
N1 C13 C14 C19 -1.3(5)
C19 C14 C15 C16 0.7(5)
C13 C14 C15 C16 179.1(3)
C14 C15 C16 C17 -1.3(5)
C14 C15 C16 C20 176.8(3)
C15 C16 C17 C18 0.1(5)
C20 C16 C17 C18 -178.0(3)
C16 C17 C18 C19 1.7(5)
C16 C17 C18 C21 177.0(3)
C15 C14 C19 O1 -178.4(3)
C13 C14 C19 O1 3.3(5)
C15 C14 C19 C18 1.1(4)
C13 C14 C19 C18 -177.2(3)
C17 C18 C19 O1 177.3(3)
C21 C18 C19 O1 2.1(4)
C17 C18 C19 C14 -2.2(4)
C21 C18 C19 C14 -177.5(3)
C14 C19 O1 Cu1 2.7(4)
C18 C19 O1 Cu1 -176.8(2)
C17 C18 C21 N2 13.9(4)
C19 C18 C21 N2 -170.8(3)
C18 C21 N2 C22 -173.0(3)
C21 N2 C22 C23 93.0(4)
C21 N2 C22 C27 -94.3(4)
C27 C22 C23 C24 4.4(5)
N2 C22 C23 C24 177.1(3)
C27 C22 C23 C28 -175.8(3)
N2 C22 C23 C28 -3.1(4)
C22 C23 C24 C25 -2.1(5)
C28 C23 C24 C25 178.1(3)
C23 C24 C25 C26 -0.7(5)
C24 C25 C26 C27 1.3(5)
C25 C26 C27 C22 1.0(5)
C25 C26 C27 C31 -175.9(3)
C23 C22 C27 C26 -3.9(5)
N2 C22 C27 C26 -176.3(3)
C23 C22 C27 C31 173.1(3)
N2 C22 C27 C31 0.6(4)
C24 C23 C28 C30 85.4(4)
C22 C23 C28 C30 -94.4(4)
C24 C23 C28 C29 -39.3(4)
C22 C23 C28 C29 140.9(3)
C26 C27 C31 C33 -22.7(4)
C22 C27 C31 C33 160.5(3)
C26 C27 C31 C32 100.8(4)
C22 C27 C31 C32 -76.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200406
