# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu2apaz1
_database_code_depnum_ccdc_archive 'CCDC 1535996'
_audit_update_record             
;
2017-03-04 deposited with the CCDC.
2017-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          425.15
_chemical_formula_moiety         'C10 H16 Cu2 N16 O2'
_chemical_formula_sum            'C10 H16 Cu2 N16 O2'
_chemical_formula_weight         519.47

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1606(19)
_cell_length_b                   7.799(3)
_cell_length_c                   9.722(3)
_cell_angle_alpha                96.29(3)
_cell_angle_beta                 92.89(2)
_cell_angle_gamma                113.31(3)
_cell_volume                     493.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1343
_cell_measurement_theta_min      3.1079
_cell_measurement_theta_max      29.0655

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             262
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.204
_shelx_estimated_absorpt_T_min   0.351
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            3490
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2004
_reflns_number_gt                1793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.0892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2004
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.58196(5) 0.86787(4) 0.91138(3) 0.02769(13) Uani 1 1 d . . . . .
OW1 O 0.8597(3) 1.1339(3) 0.8572(2) 0.0389(5) Uani 1 1 d . . . . .
HW1A H 0.965(5) 1.151(5) 0.889(4) 0.058 Uiso 1 1 d . U . . .
HW1B H 0.830(6) 1.217(5) 0.864(3) 0.058 Uiso 1 1 d . U . . .
N1 N 0.4631(3) 0.7041(3) 0.7289(2) 0.0274(5) Uani 1 1 d . . . . .
N2 N 0.6519(4) 0.9252(3) 0.5955(2) 0.0460(7) Uani 1 1 d . . . . .
H2A H 0.725238 0.993183 0.670095 0.055 Uiso 1 1 calc R U . . .
H2B H 0.677327 0.963692 0.516223 0.055 Uiso 1 1 calc R U . . .
N3 N 0.3925(4) 0.9979(4) 0.8942(2) 0.0388(6) Uani 1 1 d . . . . .
N4 N 0.2775(4) 0.9825(3) 0.7950(2) 0.0337(5) Uani 1 1 d . . . . .
N5 N 0.1702(5) 0.9672(5) 0.7001(3) 0.0583(8) Uani 1 1 d . . . . .
N6 N 0.7641(4) 0.7485(3) 0.9644(2) 0.0408(6) Uani 1 1 d . . . . .
N7 N 0.7570(4) 0.6015(3) 0.9142(2) 0.0387(6) Uani 1 1 d . . . . .
N8 N 0.7575(7) 0.4593(5) 0.8708(3) 0.0902(13) Uani 1 1 d . . . . .
C1 C 0.3116(5) 0.5333(4) 0.7349(3) 0.0390(7) Uani 1 1 d . . . . .
H1 H 0.289352 0.493310 0.821594 0.047 Uiso 1 1 calc R U . . .
C2 C 0.1901(5) 0.4166(4) 0.6218(3) 0.0468(8) Uani 1 1 d . . . . .
H2 H 0.088531 0.299907 0.630847 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2220(5) 0.4768(4) 0.4933(3) 0.0410(7) Uani 1 1 d . . . . .
H3 H 0.140080 0.401650 0.414027 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3738(5) 0.6464(4) 0.4834(3) 0.0357(6) Uani 1 1 d . . . . .
H4 H 0.395758 0.687921 0.397200 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4977(4) 0.7590(3) 0.6029(2) 0.0284(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N6 1.957(2) . y
CU1 N1 1.998(2) . y
CU1 N3 1.999(2) . y
CU1 N3 2.020(2) 2_677 y
CU1 OW1 2.370(2) . y
OW1 HW1A 0.76(4) . ?
OW1 HW1B 0.75(4) . ?
N1 C5 1.344(3) . ?
N1 C1 1.354(4) . ?
N2 C5 1.341(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 N4 1.200(3) . ?
N3 CU1 2.020(2) 2_677 ?
N4 N5 1.135(3) . ?
N6 N7 1.177(3) . ?
N7 N8 1.144(4) . ?
C1 C2 1.361(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?

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
N6 CU1 N1 96.74(9) . . y
N6 CU1 N3 169.62(9) . . y
N1 CU1 N3 92.06(9) . . y
N6 CU1 N3 93.35(10) . 2_677 y
N1 CU1 N3 161.78(10) . 2_677 y
N3 CU1 N3 76.73(10) . 2_677 y
N6 CU1 OW1 91.66(10) . . y
N1 CU1 OW1 104.92(9) . . y
N3 CU1 OW1 91.37(10) . . y
N3 CU1 OW1 89.86(10) 2_677 . y
CU1 OW1 HW1A 117(3) . . ?
CU1 OW1 HW1B 108(3) . . ?
HW1A OW1 HW1B 117(4) . . ?
C5 N1 C1 117.7(2) . . ?
C5 N1 CU1 125.65(17) . . ?
C1 N1 CU1 115.82(18) . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N4 N3 CU1 127.34(18) . . ?
N4 N3 CU1 129.01(19) . 2_677 ?
CU1 N3 CU1 103.27(10) . 2_677 ?
N5 N4 N3 179.1(3) . . ?
N7 N6 CU1 126.5(2) . . ?
N8 N7 N6 176.4(3) . . ?
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 118.0(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 N1 118.1(2) . . ?
N2 C5 C4 121.3(2) . . ?
N1 C5 C4 120.6(2) . . ?

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
C5 N1 C1 C2 -1.6(4) . . . . ?
CU1 N1 C1 C2 168.5(2) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C1 N1 C5 N2 -177.8(3) . . . . ?
CU1 N1 C5 N2 13.2(4) . . . . ?
C1 N1 C5 C4 3.0(4) . . . . ?
CU1 N1 C5 C4 -165.9(2) . . . . ?
C3 C4 C5 N2 178.4(3) . . . . ?
C3 C4 C5 N1 -2.5(4) . . . . ?

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
OW1 HW1A N6_$1 0.76(4) 2.16(4) 2.886(3) 160(4) 2_777
OW1 HW1A N7_$1 0.76(4) 2.67(4) 3.260(4) 137(3) 2_777
OW1 HW1B N8_$2 0.75(4) 2.15(4) 2.897(4) 176(4) 1_565
N2 H2A OW1 0.86 2.00 2.851(3) 171.7 .
N2 H2B N5_$3 0.86 2.43 3.262(4) 162.0 2_676

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Slow evaporation of mother liquor (MeOH-H2O)'
_exptl_crystal_preparation       ', Magnetic properties'
_chemical_compound_source        
'Recrystallisation from mother liquore (MeOH-H2O) at 6 deg. C'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu3apaz3
_database_code_depnum_ccdc_archive 'CCDC 1535998'
_audit_update_record             
;
2017-03-04 deposited with the CCDC.
2017-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          433
_chemical_formula_moiety         'C5 H6 Cu N8'
_chemical_formula_sum            'C5 H6 Cu N8'
_chemical_formula_weight         241.72

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1960(8)
_cell_length_b                   9.0920(14)
_cell_length_c                   10.1992(14)
_cell_angle_alpha                104.243(12)
_cell_angle_beta                 91.165(12)
_cell_angle_gamma                100.198(13)
_cell_volume                     458.61(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1054
_cell_measurement_theta_min      3.4963
_cell_measurement_theta_max      28.7829

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             242
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.354
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            2938
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.503
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1868
_reflns_number_gt                1581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.61741(9) 0.85589(6) 0.51392(5) 0.0356(3) Uani 1 1 d . . . . .
N1 N 0.5035(8) 0.9560(5) 0.3733(4) 0.0396(9) Uani 1 1 d . . . . .
N2 N 0.4763(8) 0.9024(4) 0.2515(4) 0.0397(9) Uani 1 1 d . . . . .
N3 N 0.4537(12) 0.8544(6) 0.1379(5) 0.0700(14) Uani 1 1 d . . . . .
N4 N 0.2220(7) 0.6732(5) 0.4650(4) 0.0448(9) Uani 1 1 d . . . . .
N5 N 0.0341(7) 0.7075(4) 0.4293(4) 0.0348(8) Uani 1 1 d . . . . .
N6 N -0.1546(8) 0.7433(6) 0.3893(4) 0.0520(12) Uani 1 1 d . . . . .
N7 N 0.7290(7) 0.7896(4) 0.6737(4) 0.0375(8) Uani 1 1 d . . . . .
N8 N 0.5335(13) 0.4836(6) 0.8442(5) 0.085(2) Uani 1 1 d . . . . .
H8A H 0.577850 0.454843 0.914331 0.102 Uiso 1 1 calc R U . . .
H8B H 0.398228 0.432049 0.792369 0.102 Uiso 1 1 calc R U . . .
C1 C 0.6032(10) 0.6624(5) 0.7047(4) 0.0435(11) Uani 1 1 d . . . . .
H1 H 0.457369 0.604306 0.649540 0.052 Uiso 1 1 calc R U . . .
C2 C 0.6791(12) 0.6126(6) 0.8150(5) 0.0524(13) Uani 1 1 d . . . . .
C3 C 0.8982(11) 0.7000(7) 0.8945(5) 0.0580(14) Uani 1 1 d . . . . .
H3 H 0.958145 0.670227 0.968739 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0259(11) 0.8303(7) 0.8634(6) 0.0595(15) Uani 1 1 d . . . . .
H4 H 1.172605 0.889816 0.917041 0.071 Uiso 1 1 calc R U . . .
C5 C 0.9384(10) 0.8743(6) 0.7526(5) 0.0504(12) Uani 1 1 d . . . . .
H5 H 1.026193 0.963831 0.732676 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N6 1.979(4) 1_655 y
CU1 N7 1.981(4) . y
CU1 N1 2.009(4) . y
CU1 N1 2.021(4) 2_676 y
CU1 N4 2.360(4) . y
N1 N2 1.212(5) . ?
N1 CU1 2.021(4) 2_676 ?
N2 N3 1.129(6) . ?
N4 N5 1.154(5) . ?
N5 N6 1.182(5) . ?
N6 CU1 1.979(4) 1_455 ?
N7 C1 1.336(6) . ?
N7 C5 1.337(6) . ?
N8 C2 1.380(7) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
C1 C2 1.386(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(8) . ?
C3 C4 1.363(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

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
N6 CU1 N7 94.95(15) 1_655 . y
N6 CU1 N1 92.37(16) 1_655 . y
N7 CU1 N1 170.74(15) . . y
N6 CU1 N1 155.82(19) 1_655 2_676 y
N7 CU1 N1 93.87(15) . 2_676 y
N1 CU1 N1 77.20(17) . 2_676 y
N6 CU1 N4 99.97(17) 1_655 . y
N7 CU1 N4 94.73(15) . . y
N1 CU1 N4 89.57(15) . . y
N1 CU1 N4 101.68(16) 2_676 . y
N2 N1 CU1 127.4(3) . . ?
N2 N1 CU1 128.8(3) . 2_676 ?
CU1 N1 CU1 102.80(17) . 2_676 ?
N3 N2 N1 178.9(6) . . ?
N5 N4 CU1 119.9(3) . . ?
N4 N5 N6 177.9(5) . . ?
N5 N6 CU1 122.0(3) . 1_455 ?
C1 N7 C5 118.9(4) . . ?
C1 N7 CU1 122.2(3) . . ?
C5 N7 CU1 118.9(3) . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N7 C1 C2 123.3(5) . . ?
N7 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N8 C2 C3 122.6(5) . . ?
N8 C2 C1 120.2(5) . . ?
C3 C2 C1 117.1(5) . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N7 C5 C4 120.7(5) . . ?
N7 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?

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
N8 H8A N8_$1 0.86 2.49 3.150(10) 134.0 2_667
N8 H8B N6_$2 0.86 2.31 3.124(7) 159.1 2_566

_refine_diff_density_max         1.141
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.126


_exptl_crystal_recrystallization_method 
'Recrystallisation from mother liquor (MeOH-H2O) at 6 deg C.'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu4apaz4
_database_code_depnum_ccdc_archive 'CCDC 1535999'
_audit_update_record             
;
2017-03-04 deposited with the CCDC.
2017-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          482
_chemical_formula_moiety         'C10 H12 Cu N10'
_chemical_formula_sum            'C10 H12 Cu N10'
_chemical_formula_weight         335.84

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   12.3425(16)
_cell_length_b                   3.5983(4)
_cell_length_c                   30.836(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.174(14)
_cell_angle_gamma                90
_cell_volume                     1369.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1489
_cell_measurement_theta_min      3.1382
_cell_measurement_theta_max      28.8497

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.606
_shelx_estimated_absorpt_T_min   0.566
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            5479
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2808
_reflns_number_gt                1992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2016/4 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1129P)²+2.5931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.2533
_refine_ls_wR_factor_gt          0.2287
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.75123(6) 0.4968(2) 0.62993(2) 0.0371(4) Uani 1 1 d . . . . .
N1 N 0.7521(4) 0.4913(13) 0.69434(18) 0.0343(12) Uani 1 1 d . . . . .
N2 N 0.7492(6) 0.4906(19) 0.8291(2) 0.064(2) Uani 1 1 d . . . . .
HN2A H 0.806142 0.554020 0.843900 0.077 Uiso 1 1 calc R U . . .
HN2B H 0.691393 0.425671 0.842271 0.077 Uiso 1 1 calc R U . . .
N3 N 0.7522(4) 0.4953(14) 0.56561(18) 0.0355(12) Uani 1 1 d . . . . .
N4 N 0.7494(5) 0.5040(18) 0.4306(2) 0.0564(17) Uani 1 1 d . . . . .
HN4A H 0.805752 0.577214 0.417025 0.068 Uiso 1 1 calc R U . . .
HN4B H 0.692412 0.434786 0.416291 0.068 Uiso 1 1 calc R U . . .
N5 N 0.8701(4) 0.1055(15) 0.63163(18) 0.0376(13) Uani 1 1 d . . . . .
N6 N 0.9613(4) 0.1796(17) 0.6247(2) 0.0434(14) Uani 1 1 d . . . . .
N7A N 1.0499(11) 0.266(16) 0.621(2) 0.076(13) Uani 0.77(15) 1 d . . P . .
N7B N 1.047(5) 0.13(3) 0.605(3) 0.058(15) Uani 0.23(15) 1 d . . P . .
N8 N 0.6328(4) 0.8911(15) 0.62911(19) 0.0403(14) Uani 1 1 d . . . . .
N9 N 0.5408(4) 0.8118(16) 0.62539(19) 0.0435(14) Uani 1 1 d . . . . .
N10A N 0.4506(10) 0.719(6) 0.6272(9) 0.072(7) Uani 0.65(4) 1 d . . P . .
N10B N 0.453246 0.802489 0.609344 0.064(10) Uani 0.35(4) 1 d . . P . .
C1 C 0.8389(5) 0.5895(17) 0.7186(2) 0.0364(15) Uani 1 1 d . . . . .
H1 H 0.901408 0.658201 0.704271 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8414(5) 0.5952(17) 0.7625(2) 0.0381(15) Uani 1 1 d . . . . .
H2 H 0.904346 0.667918 0.777208 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6614(5) 0.4033(17) 0.7167(2) 0.0349(14) Uani 1 1 d . . . . .
H3 H 0.598414 0.344569 0.701096 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6585(5) 0.3973(17) 0.7609(2) 0.0383(16) Uani 1 1 d . . . . .
H4 H 0.595113 0.329247 0.774578 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7506(6) 0.4931(17) 0.7858(2) 0.0401(15) Uani 1 1 d . . . . .
C6 C 0.8386(5) 0.6017(17) 0.5427(2) 0.0368(15) Uani 1 1 d . . . . .
H6 H 0.900379 0.675925 0.558128 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8423(5) 0.6087(17) 0.4983(2) 0.0375(15) Uani 1 1 d . . . . .
H7 H 0.904646 0.685999 0.484445 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7506(5) 0.4977(17) 0.4740(2) 0.0386(15) Uani 1 1 d . . . . .
C9 C 0.6583(5) 0.3878(17) 0.4977(2) 0.0378(15) Uani 1 1 d . . . . .
H9 H 0.595488 0.312356 0.483008 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6620(5) 0.3929(16) 0.5421(2) 0.0340(14) Uani 1 1 d . . . . .
H10 H 0.600327 0.323561 0.556881 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N3 1.984(6) . Y
CU1 N1 1.986(6) . Y
CU1 N5 2.033(5) . Y
CU1 N8 2.037(5) . Y
N1 C1 1.341(8) . ?
N1 C3 1.365(8) . ?
N2 C5 1.338(9) . ?
N2 HN2A 0.8600 . ?
N2 HN2B 0.8600 . ?
N3 C6 1.346(8) . ?
N3 C10 1.368(8) . ?
N4 C8 1.337(9) . ?
N4 HN4A 0.8600 . ?
N4 HN4B 0.8600 . ?
N5 N6 1.181(7) . ?
N6 N7A 1.15(2) . ?
N6 N7B 1.23(7) . ?
N7A N7B 0.68(6) . ?
N8 N9 1.174(7) . ?
N9 N10A 1.165(14) . ?
N9 N10B 1.180(5) . ?
N10A N10B 0.63(3) . ?
C1 C2 1.354(9) . ?
C1 H1 0.9300 . ?
C2 C5 1.393(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(9) . ?
C4 H4 0.9300 . ?
C6 C7 1.372(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.422(9) . ?
C9 C10 1.369(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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
N3 CU1 N1 179.02(19) . . Y
N3 CU1 N5 90.3(2) . . Y
N1 CU1 N5 88.8(2) . . Y
N3 CU1 N8 90.5(2) . . Y
N1 CU1 N8 90.5(2) . . Y
N5 CU1 N8 179.2(2) . . Y
C1 N1 C3 115.7(6) . . ?
C1 N1 CU1 122.8(4) . . ?
C3 N1 CU1 121.4(4) . . ?
C5 N2 HN2A 120.0 . . ?
C5 N2 HN2B 120.0 . . ?
HN2A N2 HN2B 120.0 . . ?
C6 N3 C10 116.3(6) . . ?
C6 N3 CU1 123.1(5) . . ?
C10 N3 CU1 120.7(5) . . ?
C8 N4 HN4A 120.0 . . ?
C8 N4 HN4B 120.0 . . ?
HN4A N4 HN4B 120.0 . . ?
N6 N5 CU1 121.9(5) . . ?
N7A N6 N5 175(4) . . ?
N7A N6 N7B 33(2) . . ?
N5 N6 N7B 152(6) . . ?
N7B N7A N6 81(7) . . ?
N7A N7B N6 66(7) . . ?
N9 N8 CU1 121.6(5) . . ?
N10A N9 N8 171.2(16) . . ?
N10A N9 N10B 31.1(14) . . ?
N8 N9 N10B 157.5(7) . . ?
N10B N10A N9 75.8(17) . . ?
N10A N10B N9 73.1(12) . . ?
N1 C1 C2 124.2(6) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C5 120.7(6) . . ?
C1 C2 H2 119.7 . . ?
C5 C2 H2 119.7 . . ?
C4 C3 N1 123.2(6) . . ?
C4 C3 H3 118.4 . . ?
N1 C3 H3 118.4 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C2 123.0(7) . . ?
N2 C5 C4 121.3(7) . . ?
C2 C5 C4 115.7(6) . . ?
N3 C6 C7 124.9(6) . . ?
N3 C6 H6 117.5 . . ?
C7 C6 H6 117.5 . . ?
C6 C7 C8 119.0(6) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
N4 C8 C7 121.4(6) . . ?
N4 C8 C9 121.8(6) . . ?
C7 C8 C9 116.8(6) . . ?
C10 C9 C8 120.0(6) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N3 C10 C9 123.0(6) . . ?
N3 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?

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 N5 N6 N7B -127(7) . . . . ?
N5 N6 N7B N7A -177.1(18) . . . . ?
CU1 N8 N9 N10B -117.8(14) . . . . ?
N8 N9 N10B N10A -176(2) . . . . ?
C3 N1 C1 C2 1.8(9) . . . . ?
CU1 N1 C1 C2 178.8(5) . . . . ?
N1 C1 C2 C5 0.4(10) . . . . ?
C1 N1 C3 C4 -2.9(9) . . . . ?
CU1 N1 C3 C4 -179.8(5) . . . . ?
N1 C3 C4 C5 1.6(10) . . . . ?
C1 C2 C5 N2 179.4(7) . . . . ?
C1 C2 C5 C4 -1.7(9) . . . . ?
C3 C4 C5 N2 179.7(6) . . . . ?
C3 C4 C5 C2 0.7(9) . . . . ?
C10 N3 C6 C7 -0.9(9) . . . . ?
CU1 N3 C6 C7 -179.2(5) . . . . ?
N3 C6 C7 C8 -0.1(9) . . . . ?
C6 C7 C8 N4 179.1(6) . . . . ?
C6 C7 C8 C9 0.7(9) . . . . ?
N4 C8 C9 C10 -178.6(6) . . . . ?
C7 C8 C9 C10 -0.1(9) . . . . ?
C6 N3 C10 C9 1.5(9) . . . . ?
CU1 N3 C10 C9 179.9(5) . . . . ?
C8 C9 C10 N3 -1.0(9) . . . . ?

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
N2 HN2A N7A_$1 0.86 2.20 3.06(2) 174.8 2_756
N2 HN2A N7B_$1 0.86 2.38 3.23(7) 168.4 2_756
N2 HN2B N10A_$2 0.86 2.14 2.997(18) 175.3 2_646
N2 HN2B N10B_$2 0.86 2.39 3.240(7) 168.9 2_646
N4 HN4A N7A_$3 0.86 2.22 3.08(2) 176.2 3_766
N4 HN4A N7B_$3 0.86 2.22 3.06(6) 166.2 3_766
N4 HN4B N10A_$4 0.86 2.26 3.121(17) 174.3 3_666
N4 HN4B N10B_$4 0.86 2.13 2.978(6) 169.5 3_666

_refine_diff_density_max         2.487
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.147


_exptl_crystal_recrystallization_method 
'Slow diffusion of layered reactant solutions at 32 deg. C'
_exptl_crystal_preparation       ', Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu3apaz2
_database_code_depnum_ccdc_archive 'CCDC 1535997'
_audit_update_record             
;
2017-03-04 deposited with the CCDC.
2017-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          431
_chemical_formula_moiety         'C10 H12 Cu3 N22'
_chemical_formula_sum            'C10 H12 Cu3 N22'
_chemical_formula_weight         631.04

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   15.3165(9)
_cell_length_b                   6.0322(4)
_cell_length_c                   23.3287(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.287(6)
_cell_angle_gamma                90
_cell_volume                     2149.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1975
_cell_measurement_theta_min      3.0276
_cell_measurement_theta_max      29.0769

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.995
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance Mo Ka source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_reflns_number            9238
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4398
_reflns_number_gt                2938
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4398
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.09854(4) 0.61072(11) 0.23836(3) 0.02172(19) Uani 1 1 d . . . . .
CU2 Cu 0.25680(4) 0.35049(13) 0.29532(3) 0.0309(2) Uani 1 1 d . . . . .
CU3 Cu 0.48838(4) 0.19768(11) 0.25104(3) 0.02025(19) Uani 1 1 d . . . . .
N1 N 0.0698(3) 0.6947(8) 0.1571(2) 0.0242(11) Uani 1 1 d . . . . .
N2 N 0.1603(4) 1.0242(11) 0.0458(3) 0.071(2) Uani 1 1 d . . . . .
H2A H 0.202579 1.088146 0.065728 0.086 Uiso 1 1 calc R U . . .
H2B H 0.151527 1.051423 0.009653 0.086 Uiso 1 1 calc R U . . .
N3 N 0.2953(3) 0.3011(10) 0.3765(2) 0.0370(14) Uani 1 1 d . . . . .
N4 N 0.2570(6) -0.0604(15) 0.4913(4) 0.133(4) Uani 1 1 d . . . . .
H4A H 0.270245 -0.075261 0.527547 0.159 Uiso 1 1 calc R U . . .
H4B H 0.222412 -0.153779 0.473392 0.159 Uiso 1 1 calc R U . . .
N5 N 0.2098(3) 0.4591(8) 0.2193(2) 0.0270(12) Uani 1 1 d . . . . .
N6 N 0.2364(3) 0.4203(8) 0.1735(2) 0.0302(12) Uani 1 1 d . . . . .
N7 N 0.2624(4) 0.3854(11) 0.1297(3) 0.062(2) Uani 1 1 d . . . . .
N8 N 0.1479(3) 0.5090(8) 0.3158(2) 0.0229(11) Uani 1 1 d . . . . .
N9 N 0.1341(3) 0.5765(8) 0.3621(2) 0.0260(12) Uani 1 1 d . . . . .
N10 N 0.1220(4) 0.6369(10) 0.4069(2) 0.0529(17) Uani 1 1 d . . . . .
N11 N -0.0166(3) 0.7059(8) 0.26649(19) 0.0235(11) Uani 1 1 d . . . . .
N12 N -0.0796(3) 0.6012(8) 0.2503(2) 0.0233(11) Uani 1 1 d . . . . .
N13 N -0.1427(3) 0.5008(8) 0.2348(2) 0.0320(13) Uani 1 1 d . . . . .
N14 N 0.3420(3) 0.1401(8) 0.2673(2) 0.0264(12) Uani 1 1 d . . . . .
N15 N 0.3349(3) -0.0526(9) 0.2808(2) 0.0276(12) Uani 1 1 d . . . . .
N16 N 0.3339(3) -0.2380(9) 0.2919(3) 0.0477(17) Uani 1 1 d . . . . .
N17 N 0.4674(3) 0.4518(7) 0.1971(2) 0.0234(11) Uani 1 1 d . . . . .
N18 N 0.4833(3) 0.4401(8) 0.1467(3) 0.0308(13) Uani 1 1 d . . . . .
N19 N 0.4972(4) 0.4279(10) 0.0995(3) 0.0600(18) Uani 1 1 d . . . . .
N20 N 0.5161(3) 0.4473(7) 0.3054(2) 0.0241(11) Uani 1 1 d . . . . .
N21 N 0.5744(4) 0.4326(8) 0.3436(2) 0.0381(14) Uani 1 1 d . . . . .
N22 N 0.6294(5) 0.4166(11) 0.3801(3) 0.081(3) Uani 1 1 d . . . . .
C1 C 0.1197(4) 0.8323(10) 0.1298(3) 0.0326(16) Uani 1 1 d . . . . .
H1 H 0.165912 0.901766 0.150723 0.039 Uiso 1 1 calc R U . . .
C2 C 0.1066(4) 0.8782(11) 0.0718(3) 0.0352(16) Uani 1 1 d . . . . .
C3 C 0.0377(4) 0.7723(11) 0.0411(3) 0.0382(17) Uani 1 1 d . . . . .
H3 H 0.027370 0.795140 0.001773 0.046 Uiso 1 1 calc R U . . .
C4 C -0.0144(4) 0.6353(11) 0.0694(3) 0.0381(17) Uani 1 1 d . . . . .
H4 H -0.062019 0.567055 0.049502 0.046 Uiso 1 1 calc R U . . .
C5 C 0.0025(4) 0.5964(10) 0.1270(3) 0.0317(15) Uani 1 1 d . . . . .
H5 H -0.033331 0.499817 0.145565 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2669(4) 0.1327(13) 0.4051(3) 0.0455(19) Uani 1 1 d . . . . .
H6 H 0.230439 0.028862 0.386002 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2898(5) 0.1054(14) 0.4631(4) 0.057(2) Uani 1 1 d . . . . .
C8 C 0.3452(5) 0.2558(17) 0.4913(3) 0.064(3) Uani 1 1 d . . . . .
H8 H 0.361334 0.235395 0.530159 0.077 Uiso 1 1 calc R U . . .
C9 C 0.3766(5) 0.4322(15) 0.4639(4) 0.066(3) Uani 1 1 d . . . . .
H9 H 0.413724 0.536310 0.482287 0.079 Uiso 1 1 calc R U . . .
C10 C 0.3486(4) 0.4461(13) 0.4047(3) 0.051(2) Uani 1 1 d . . . . .
H10 H 0.368865 0.564835 0.383992 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 1.980(5) . y
CU1 N8 2.002(5) . y
CU1 N11 2.011(4) . y
CU1 N5 2.012(5) . y
CU1 N13 2.514(5) 2 y
CU1 N11 2.744(5) 2_545 y
CU1 CU2 3.1022(9) . y
CU1 N16 3.836(5) 1_565 y
CU1 CU1 4.3299(9) 2 y
CU1 CU2 5.2032(11) 1_565 y
CU2 N3 1.964(5) . y
CU2 N14 1.967(5) . y
CU2 N5 1.975(5) . y
CU2 N8 2.011(4) . y
CU2 N16 2.753(5) 1_565 y
CU2 N13 2.796(5) 2_545 y
CU2 CU3 3.8788(10) . y
CU3 N20 1.994(5) . y
CU3 N17 1.994(5) . y
CU3 N17 2.000(5) 2_645 y
CU3 N20 2.001(5) 2_645 y
CU3 N14 2.328(4) . y
CU3 CU3 3.0379(3) 2_655 y
CU3 CU3 3.0379(3) 2_645 y
N1 C1 1.324(7) . ?
N1 C5 1.341(7) . ?
N2 C2 1.375(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C6 1.308(8) . ?
N3 C10 1.336(8) . ?
N4 C7 1.316(10) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 N6 1.196(6) . ?
N6 N7 1.143(7) . ?
N8 N9 1.188(6) . ?
N9 N10 1.134(6) . ?
N11 N12 1.190(6) . ?
N12 N13 1.175(6) . ?
N14 N15 1.211(6) . ?
N15 N16 1.149(6) . ?
N17 N18 1.220(7) . ?
N17 CU3 2.000(5) 2_655 ?
N18 N19 1.140(7) . ?
N20 N21 1.217(6) . ?
N20 CU3 2.001(5) 2_655 ?
N21 N22 1.157(7) . ?
C1 C2 1.380(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(8) . ?
C3 C4 1.354(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.382(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(11) . ?
C8 C9 1.350(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.416(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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
N1 CU1 N8 169.90(18) . . y
N1 CU1 N11 95.83(18) . . y
N8 CU1 N11 94.27(18) . . y
N1 CU1 N5 92.09(19) . . y
N8 CU1 N5 77.92(18) . . y
N11 CU1 N5 168.35(19) . . y
N1 CU1 N13 92.04(18) . 2 y
N8 CU1 N13 89.18(18) . 2 y
N11 CU1 N13 82.98(18) . 2 y
N5 CU1 N13 105.31(18) . 2 y
N1 CU1 N11 96.88(17) . 2_545 y
N8 CU1 N11 84.56(16) . 2_545 y
N11 CU1 N11 81.84(10) . 2_545 y
N5 CU1 N11 88.76(17) . 2_545 y
N13 CU1 N11 163.08(15) 2 2_545 y
N1 CU1 CU2 130.57(13) . . y
N8 CU1 CU2 39.47(13) . . y
N11 CU1 CU2 132.92(13) . . y
N5 CU1 CU2 38.48(13) . . y
N13 CU1 CU2 100.36(11) 2 . y
N11 CU1 CU2 84.70(10) 2_545 . y
N1 CU1 N16 112.79(16) . 1_565 y
N8 CU1 N16 59.79(16) . 1_565 y
N11 CU1 N16 130.68(16) . 1_565 y
N5 CU1 N16 52.36(16) . 1_565 y
N13 CU1 N16 57.84(13) 2 1_565 y
N11 CU1 N16 129.85(13) 2_545 1_565 y
CU2 CU1 N16 45.23(8) . 1_565 y
N1 CU1 CU1 80.47(13) . 2 y
N8 CU1 CU1 108.68(13) . 2 y
N11 CU1 CU1 28.79(13) . 2 y
N5 CU1 CU1 162.54(14) . 2 y
N13 CU1 CU1 59.60(10) 2 2 y
N11 CU1 CU1 107.71(10) 2_545 2 ?
CU2 CU1 CU1 145.95(3) . 2 ?
N16 CU1 CU1 116.14(9) 1_565 2 ?
N1 CU1 CU2 95.23(14) . 1_565 ?
N8 CU1 CU2 83.98(13) . 1_565 ?
N11 CU1 CU2 94.31(14) . 1_565 ?
N5 CU1 CU2 93.45(14) . 1_565 ?
N13 CU1 CU2 12.14(10) 2 1_565 ?
N11 CU1 CU2 167.60(10) 2_545 1_565 ?
CU2 CU1 CU2 89.45(2) . 1_565 ?
N16 CU1 CU2 45.92(8) 1_565 1_565 ?
CU1 CU1 CU2 71.725(11) 2 1_565 ?
N3 CU2 N14 93.7(2) . . ?
N3 CU2 N5 168.3(2) . . ?
N14 CU2 N5 97.0(2) . . ?
N3 CU2 N8 92.13(19) . . ?
N14 CU2 N8 165.57(19) . . ?
N5 CU2 N8 78.59(19) . . ?
N3 CU2 N16 93.8(2) . 1_565 ?
N14 CU2 N16 105.99(18) . 1_565 ?
N5 CU2 N16 78.66(19) . 1_565 ?
N8 CU2 N16 86.77(18) . 1_565 ?
N3 CU2 N13 105.3(2) . 2_545 ?
N14 CU2 N13 81.21(16) . 2_545 ?
N5 CU2 N13 81.11(18) . 2_545 ?
N8 CU2 N13 84.51(17) . 2_545 ?
N16 CU2 N13 159.19(16) 1_565 2_545 ?
N3 CU2 CU1 131.17(14) . . ?
N14 CU2 CU1 134.48(15) . . ?
N5 CU2 CU1 39.34(14) . . ?
N8 CU2 CU1 39.27(13) . . ?
N16 CU2 CU1 81.64(11) 1_565 . ?
N13 CU2 CU1 79.65(10) 2_545 . ?
N3 CU2 CU3 90.37(14) . . ?
N14 CU2 CU3 27.82(13) . . ?
N5 CU2 CU3 96.86(14) . . ?
N8 CU2 CU3 165.36(14) . . ?
N16 CU2 CU3 78.67(11) 1_565 . ?
N13 CU2 CU3 108.71(10) 2_545 . ?
CU1 CU2 CU3 134.99(3) . . ?
N20 CU3 N17 80.63(19) . . ?
N20 CU3 N17 97.42(19) . 2_645 ?
N17 CU3 N17 169.47(6) . 2_645 ?
N20 CU3 N20 169.58(4) . 2_645 ?
N17 CU3 N20 99.74(19) . 2_645 ?
N17 CU3 N20 80.31(19) 2_645 2_645 ?
N20 CU3 N14 99.85(18) . . ?
N17 CU3 N14 96.05(17) . . ?
N17 CU3 N14 94.47(17) 2_645 . ?
N20 CU3 N14 90.49(18) 2_645 . ?
N20 CU3 CU3 40.59(13) . 2_655 ?
N17 CU3 CU3 40.55(13) . 2_655 ?
N17 CU3 CU3 135.32(14) 2_645 2_655 ?
N20 CU3 CU3 137.48(14) 2_645 2_655 ?
N14 CU3 CU3 105.44(12) . 2_655 ?
N20 CU3 CU3 137.78(14) . 2_645 ?
N17 CU3 CU3 140.06(14) . 2_645 ?
N17 CU3 CU3 40.42(14) 2_645 2_645 ?
N20 CU3 CU3 40.40(13) 2_645 2_645 ?
N14 CU3 CU3 88.27(12) . 2_645 ?
CU3 CU3 CU3 166.28(5) 2_655 2_645 ?
N20 CU3 CU2 78.85(13) . . ?
N17 CU3 CU2 82.97(13) . . ?
N17 CU3 CU2 106.89(14) 2_645 . ?
N20 CU3 CU2 111.57(13) 2_645 . ?
N14 CU3 CU2 23.22(12) . . ?
CU3 CU3 CU2 83.05(3) 2_655 . ?
CU3 CU3 CU2 110.54(3) 2_645 . ?
C1 N1 C5 118.2(5) . . ?
C1 N1 CU1 121.8(4) . . ?
C5 N1 CU1 119.8(4) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C6 N3 C10 118.1(6) . . ?
C6 N3 CU2 121.5(5) . . ?
C10 N3 CU2 120.3(5) . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N6 N5 CU2 127.7(4) . . ?
N6 N5 CU1 129.6(4) . . ?
CU2 N5 CU1 102.2(2) . . ?
N7 N6 N5 179.2(7) . . ?
N9 N8 CU1 129.4(4) . . ?
N9 N8 CU2 125.9(4) . . ?
CU1 N8 CU2 101.3(2) . . ?
N10 N9 N8 178.4(6) . . ?
N12 N11 CU1 117.0(4) . . ?
N13 N12 N11 178.8(6) . . ?
N15 N14 CU2 117.3(4) . . ?
N15 N14 CU3 106.9(4) . . ?
CU2 N14 CU3 129.0(2) . . ?
N16 N15 N14 175.1(6) . . ?
N18 N17 CU3 121.9(4) . . ?
N18 N17 CU3 122.9(4) . 2_655 ?
CU3 N17 CU3 99.0(2) . 2_655 ?
N19 N18 N17 179.2(7) . . ?
N21 N20 CU3 121.4(4) . . ?
N21 N20 CU3 121.6(4) . 2_655 ?
CU3 N20 CU3 99.0(2) . 2_655 ?
N22 N21 N20 179.2(7) . . ?
N1 C1 C2 123.5(6) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C2 C1 120.8(6) . . ?
N2 C2 C3 121.7(6) . . ?
C1 C2 C3 117.5(6) . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 121.4(6) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N3 C6 C7 121.5(7) . . ?
N3 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
N4 C7 C8 120.5(9) . . ?
N4 C7 C6 120.0(9) . . ?
C8 C7 C6 119.5(8) . . ?
C9 C8 C7 121.5(8) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 114.6(8) . . ?
C8 C9 H9 122.7 . . ?
C10 C9 H9 122.7 . . ?
N3 C10 C9 124.8(7) . . ?
N3 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?

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
C5 N1 C1 C2 -0.7(9) . . . . ?
CU1 N1 C1 C2 173.5(5) . . . . ?
N1 C1 C2 N2 179.5(6) . . . . ?
N1 C1 C2 C3 -0.3(10) . . . . ?
N2 C2 C3 C4 -178.1(6) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C3 C4 C5 -2.1(10) . . . . ?
C1 N1 C5 C4 0.3(9) . . . . ?
CU1 N1 C5 C4 -174.0(5) . . . . ?
C3 C4 C5 N1 1.1(10) . . . . ?
C10 N3 C6 C7 1.0(10) . . . . ?
CU2 N3 C6 C7 -176.0(5) . . . . ?
N3 C6 C7 N4 177.0(8) . . . . ?
N3 C6 C7 C8 -1.4(11) . . . . ?
N4 C7 C8 C9 -177.2(8) . . . . ?
C6 C7 C8 C9 1.2(12) . . . . ?
C7 C8 C9 C10 -0.6(11) . . . . ?
C6 N3 C10 C9 -0.4(10) . . . . ?
CU2 N3 C10 C9 176.6(5) . . . . ?
C8 C9 C10 N3 0.2(11) . . . . ?

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
N2 H2A N7_$1 0.86 2.47 3.251(9) 152.2 1_565
N2 H2B N10_$2 0.86 2.66 3.392(9) 143.7 4_575
N4 H4A N7_$3 0.86 2.66 3.393(10) 144.6 4_566
N4 H4B N10_$4 0.86 2.45 3.298(10) 168.3 1_545

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.129


_exptl_crystal_recrystallization_method 
'slow diffusion by layering of reactant solutions'
_exptl_crystal_preparation       ', Magnetic properties'
