#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/35/7023561.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_7023561
loop_
_publ_author_name
'Chi, Yan-Hui'
'Shi, Jing-Min'
'Li, Hong-Nan'
'Wei, Wei'
'Cottrill, Ethan'
'Pan, Ning'
'Chen, Hu'
'Liang, Yuan'
'Yu, Li'
'Zhang, Yi-Quan'
'Hou, Chao'
_publ_section_title
;
 π-π Stacking, spin density and magnetic coupling strength.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15559
_journal_page_last               15569
_journal_paper_doi               10.1039/c3dt51476e
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C16 H15 Cu N7 O7'
_chemical_formula_weight         480.89
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.245(17)
_cell_angle_beta                 85.180(18)
_cell_angle_gamma                73.112(15)
_cell_formula_units_Z            2
_cell_length_a                   9.188(12)
_cell_length_b                   9.476(12)
_cell_length_c                   12.122(15)
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.1915
_cell_measurement_theta_min      2.317
_cell_volume                     944(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5162
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.8293
_exptl_absorpt_correction_T_min  0.7931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0876P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                2909
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt51476e.txt
_cod_data_source_block           101111am
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7023561
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6271(5) 0.3032(5) 0.7857(4) 0.0525(10) Uani 1 1 d .
H1 H 0.7053 0.2522 0.7475 0.063 Uiso 1 1 calc R
C2 C 0.5432(6) 0.2161(5) 0.8702(4) 0.0598(12) Uani 1 1 d .
H2 H 0.5677 0.1079 0.8881 0.072 Uiso 1 1 calc R
C3 C 0.4264(5) 0.2873(5) 0.9265(4) 0.0581(11) Uani 1 1 d .
H3 H 0.3697 0.2284 0.9807 0.070 Uiso 1 1 calc R
C4 C 0.3918(4) 0.4498(5) 0.9026(3) 0.0479(10) Uani 1 1 d .
C5 C 0.4828(4) 0.5276(4) 0.8187(3) 0.0404(8) Uani 1 1 d .
C6 C 0.2769(5) 0.5404(6) 0.9559(4) 0.0591(12) Uani 1 1 d .
H6 H 0.2157 0.4902 1.0119 0.071 Uiso 1 1 calc R
C7 C 0.2533(5) 0.6960(6) 0.9287(4) 0.0562(11) Uani 1 1 d .
H7 H 0.1769 0.7505 0.9660 0.067 Uiso 1 1 calc R
C8 C 0.3445(4) 0.7788(5) 0.8428(3) 0.0452(9) Uani 1 1 d .
C9 C 0.4581(4) 0.6923(4) 0.7916(3) 0.0399(8) Uani 1 1 d .
C10 C 0.3344(5) 0.9402(5) 0.8071(4) 0.0530(10) Uani 1 1 d .
H10 H 0.2609 1.0041 0.8396 0.064 Uiso 1 1 calc R
C11 C 0.4310(4) 1.0043(5) 0.7253(4) 0.0483(10) Uani 1 1 d .
H11 H 0.4229 1.1111 0.7014 0.058 Uiso 1 1 calc R
C12 C 0.5418(4) 0.9061(4) 0.6788(3) 0.0396(8) Uani 1 1 d .
C13 C 0.6780(4) 1.0870(4) 0.5356(3) 0.0443(9) Uani 1 1 d .
H13 H 0.6297 1.1825 0.5454 0.053 Uiso 1 1 calc R
C14 C 0.7928(4) 1.0618(5) 0.4608(4) 0.0463(9) Uani 1 1 d .
H14 H 0.8381 1.1358 0.4099 0.056 Uiso 1 1 calc R
C15 C 0.8300(4) 0.9001(4) 0.4759(3) 0.0407(8) Uani 1 1 d .
C16 C 1.0159(6) 0.3950(6) 0.8056(5) 0.0794(15) Uani 1 1 d .
H16A H 0.9760 0.3111 0.8076 0.119 Uiso 1 1 calc R
H16B H 1.0487 0.3779 0.8836 0.119 Uiso 1 1 calc R
H16C H 1.1007 0.3978 0.7537 0.119 Uiso 1 1 calc R
Cu1 Cu 0.70254(5) 0.61817(5) 0.64584(4) 0.03951(19) Uani 1 1 d .
N1 N 0.5964(4) 0.4586(4) 0.7591(3) 0.0427(7) Uani 1 1 d .
N2 N 0.5544(3) 0.7547(3) 0.7120(3) 0.0380(7) Uani 1 1 d .
N3 N 0.6460(3) 0.9492(3) 0.5931(3) 0.0412(7) Uani 1 1 d .
N4 N 0.7392(3) 0.8310(3) 0.5558(3) 0.0414(7) Uani 1 1 d .
N5 N 0.9336(4) 0.8231(4) 0.4200(3) 0.0539(9) Uani 1 1 d .
H5A H 0.9448 0.7249 0.4343 0.065 Uiso 1 1 calc R
H5B H 0.9901 0.8710 0.3692 0.065 Uiso 1 1 calc R
N6 N 0.7185(4) 0.5136(4) 0.4655(3) 0.0489(8) Uani 1 1 d .
N7 N 0.8953(5) 0.8831(5) 0.8082(5) 0.0761(12) Uani 1 1 d .
H4 H 0.9384 0.6237 0.7585 0.114 Uiso 1 1 d RD
O1 O 0.9021(3) 0.5388(4) 0.7644(3) 0.0710(9) Uani 1 1 d D
O2 O 0.9776(5) 0.8078(6) 0.7450(4) 0.0983(13) Uani 1 1 d .
O3 O 0.8111(6) 0.8253(8) 0.8732(5) 0.142(2) Uani 1 1 d .
O4 O 0.9128(6) 1.0095(5) 0.7920(5) 0.1233(17) Uani 1 1 d .
O5 O 0.6000(4) 0.6187(4) 0.4506(3) 0.0680(9) Uani 1 1 d .
O6 O 0.7577(4) 0.4321(4) 0.4045(3) 0.0817(11) Uani 1 1 d .
O7 O 0.8076(3) 0.4886(3) 0.5525(3) 0.0531(7) 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'
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
N1 C1 C2 121.0(4)
N1 C1 H1 119.5
C2 C1 H1 119.5
C3 C2 C1 121.1(4)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 119.8(4)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 115.5(4)
C5 C4 C6 117.8(4)
C3 C4 C6 126.6(4)
N1 C5 C4 125.2(4)
N1 C5 C9 115.7(3)
C4 C5 C9 119.1(4)
C7 C6 C4 122.6(4)
C7 C6 H6 118.7
C4 C6 H6 118.7
C6 C7 C8 120.8(4)
C6 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C10 115.6(4)
C9 C8 C7 117.4(4)
C10 C8 C7 126.9(4)
N2 C9 C8 123.5(4)
N2 C9 C5 114.3(3)
C8 C9 C5 122.2(4)
C11 C10 C8 121.1(4)
C11 C10 H10 119.5
C8 C10 H10 119.4
C10 C11 C12 118.6(4)
C10 C11 H11 120.7
C12 C11 H11 120.7
N2 C12 N3 111.5(3)
N2 C12 C11 121.3(4)
N3 C12 C11 127.2(4)
N3 C13 C14 108.0(3)
N3 C13 H13 126.0
C14 C13 H13 126.0
C13 C14 C15 106.1(3)
C13 C14 H14 126.9
C15 C14 H14 126.9
N5 C15 N4 122.4(4)
N5 C15 C14 127.6(4)
N4 C15 C14 110.0(3)
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N2 Cu1 O7 164.90(12)
N2 Cu1 N4 77.84(15)
O7 Cu1 N4 103.43(15)
N2 Cu1 N1 80.16(16)
O7 Cu1 N1 97.10(15)
N4 Cu1 N1 157.82(13)
N2 Cu1 O1 102.59(15)
O7 Cu1 O1 92.39(15)
N4 Cu1 O1 93.54(13)
N1 Cu1 O1 93.92(15)
C1 N1 C5 117.4(4)
C1 N1 Cu1 130.7(3)
C5 N1 Cu1 111.8(3)
C12 N2 C9 120.0(3)
C12 N2 Cu1 122.0(3)
C9 N2 Cu1 118.0(3)
C13 N3 C12 132.9(3)
C13 N3 N4 110.6(3)
C12 N3 N4 116.4(3)
C15 N4 N3 105.2(3)
C15 N4 Cu1 142.4(3)
N3 N4 Cu1 112.2(2)
C15 N5 H5A 120.0
C15 N5 H5B 120.0
H5A N5 H5B 120.0
O6 N6 O5 124.1(4)
O6 N6 O7 118.6(3)
O5 N6 O7 117.3(3)
O3 N7 O4 126.6(6)
O3 N7 O2 118.3(5)
O4 N7 O2 115.0(5)
C16 O1 Cu1 132.1(3)
C16 O1 H4 111.7
Cu1 O1 H4 110.4
N6 O7 Cu1 108.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.338(5)
C1 C2 1.400(6)
C1 H1 0.9300
C2 C3 1.363(6)
C2 H2 0.9300
C3 C4 1.404(6)
C3 H3 0.9300
C4 C5 1.401(5)
C4 C6 1.422(6)
C5 N1 1.360(5)
C5 C9 1.427(5)
C6 C7 1.346(7)
C6 H6 0.9300
C7 C8 1.435(6)
C7 H7 0.9300
C8 C9 1.379(5)
C8 C10 1.410(6)
C9 N2 1.349(5)
C10 C11 1.371(6)
C10 H10 0.9300
C11 C12 1.395(5)
C11 H11 0.9300
C12 N2 1.317(5)
C12 N3 1.387(5)
C13 N3 1.349(5)
C13 C14 1.356(6)
C13 H13 0.9300
C14 C15 1.416(6)
C14 H14 0.9300
C15 N5 1.317(5)
C15 N4 1.340(5)
C16 O1 1.406(6)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
Cu1 N2 1.923(3)
Cu1 O7 1.957(3)
Cu1 N4 2.035(4)
Cu1 N1 2.069(4)
Cu1 O1 2.206(4)
N3 N4 1.389(4)
N5 H5A 0.8600
N5 H5B 0.8600
N6 O6 1.213(4)
N6 O5 1.219(4)
N6 O7 1.301(4)
N7 O3 1.165(6)
N7 O4 1.200(6)
N7 O2 1.283(6)
O1 H4 0.9352
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5A O7 0.86 2.54 3.138(5) 127.4 2_766
N5 H5B O4 0.86 2.15 2.985(7) 163.8 2_776
O1 H4 O2 0.94 1.83 2.758(6) 170.9 .
O1 H4 N7 0.94 2.65 3.469(7) 147.0 .
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
N1 C1 C2 C3 1.0(6)
C1 C2 C3 C4 -2.0(7)
C2 C3 C4 C5 0.7(6)
C2 C3 C4 C6 -178.1(4)
C3 C4 C5 N1 1.6(6)
C6 C4 C5 N1 -179.5(4)
C3 C4 C5 C9 -178.2(3)
C6 C4 C5 C9 0.8(5)
C5 C4 C6 C7 0.1(6)
C3 C4 C6 C7 178.9(4)
C4 C6 C7 C8 0.1(6)
C6 C7 C8 C9 -1.2(6)
C6 C7 C8 C10 -178.9(4)
C10 C8 C9 N2 -0.3(5)
C7 C8 C9 N2 -178.3(3)
C10 C8 C9 C5 -180.0(3)
C7 C8 C9 C5 2.1(5)
N1 C5 C9 N2 -1.4(5)
C4 C5 C9 N2 178.4(3)
N1 C5 C9 C8 178.3(3)
C4 C5 C9 C8 -1.9(5)
C9 C8 C10 C11 1.0(6)
C7 C8 C10 C11 178.7(4)
C8 C10 C11 C12 -0.9(6)
C10 C11 C12 N2 0.0(6)
C10 C11 C12 N3 177.8(3)
N3 C13 C14 C15 -0.1(4)
C13 C14 C15 N5 178.9(4)
C13 C14 C15 N4 0.8(4)
C2 C1 N1 C5 1.1(6)
C2 C1 N1 Cu1 177.0(3)
C4 C5 N1 C1 -2.5(5)
C9 C5 N1 C1 177.3(3)
C4 C5 N1 Cu1 -179.1(3)
C9 C5 N1 Cu1 0.6(4)
N2 Cu1 N1 C1 -176.0(4)
O7 Cu1 N1 C1 19.1(4)
N4 Cu1 N1 C1 176.8(3)
O1 Cu1 N1 C1 -73.8(4)
N2 Cu1 N1 C5 0.1(2)
O7 Cu1 N1 C5 -164.9(2)
N4 Cu1 N1 C5 -7.2(5)
O1 Cu1 N1 C5 102.2(3)
N3 C12 N2 C9 -177.4(3)
C11 C12 N2 C9 0.6(5)
N3 C12 N2 Cu1 0.2(4)
C11 C12 N2 Cu1 178.2(3)
C8 C9 N2 C12 -0.5(5)
C5 C9 N2 C12 179.2(3)
C8 C9 N2 Cu1 -178.2(3)
C5 C9 N2 Cu1 1.5(4)
O7 Cu1 N2 C12 -97.9(5)
N4 Cu1 N2 C12 -1.4(3)
N1 Cu1 N2 C12 -178.6(3)
O1 Cu1 N2 C12 89.6(3)
O7 Cu1 N2 C9 79.8(5)
N4 Cu1 N2 C9 176.3(3)
N1 Cu1 N2 C9 -0.9(3)
O1 Cu1 N2 C9 -92.8(3)
C14 C13 N3 C12 179.5(4)
C14 C13 N3 N4 -0.6(4)
N2 C12 N3 C13 -178.3(4)
C11 C12 N3 C13 3.8(6)
N2 C12 N3 N4 1.9(4)
C11 C12 N3 N4 -176.1(3)
N5 C15 N4 N3 -179.3(3)
C14 C15 N4 N3 -1.2(4)
N5 C15 N4 Cu1 6.6(6)
C14 C15 N4 Cu1 -175.2(3)
C13 N3 N4 C15 1.1(4)
C12 N3 N4 C15 -179.0(3)
C13 N3 N4 Cu1 177.2(2)
C12 N3 N4 Cu1 -2.9(4)
N2 Cu1 N4 C15 176.0(4)
O7 Cu1 N4 C15 -19.4(4)
N1 Cu1 N4 C15 -176.7(4)
O1 Cu1 N4 C15 73.9(4)
N2 Cu1 N4 N3 2.2(2)
O7 Cu1 N4 N3 166.8(2)
N1 Cu1 N4 N3 9.5(5)
O1 Cu1 N4 N3 -99.9(3)
N2 Cu1 O1 C16 145.0(4)
O7 Cu1 O1 C16 -33.0(5)
N4 Cu1 O1 C16 -136.7(5)
N1 Cu1 O1 C16 64.2(5)
O6 N6 O7 Cu1 -172.7(3)
O5 N6 O7 Cu1 7.4(4)
N2 Cu1 O7 N6 10.0(6)
N4 Cu1 O7 N6 -83.0(3)
N1 Cu1 O7 N6 88.5(3)
O1 Cu1 O7 N6 -177.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139160643
