# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1418682'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cu3 N20'
_chemical_formula_sum            'C10 H10 Cu3 N20'
_chemical_formula_weight         601.00

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P_2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.664(2)
_cell_length_b                   11.639(2)
_cell_length_c                   8.0406(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.73(3)
_cell_angle_gamma                90.00
_cell_volume                     997.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2560
_cell_measurement_theta_min      2.5332
_cell_measurement_theta_max      27.9283

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark green'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    3.218
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8979
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10710
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.93
_reflns_number_total             2394
_reflns_number_gt                2115
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        "CrystalStructure (Rigaku/MSC'2004)"
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.1146P] 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         2394
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.92909(3) 0.39011(3) 0.15968(4) 0.01336(11) Uani 1 1 d . . .
Cu2 Cu 1.0000 0.5000 0.5000 0.01463(13) Uani 1 2 d S . .
N1 N 0.7651(2) 0.37105(19) 0.0408(3) 0.0143(4) Uani 1 1 d . . .
N2 N 1.0782(2) 0.4140(2) 0.3144(3) 0.0147(5) Uani 1 1 d . . .
N3 N 1.1719(2) 0.3539(2) 0.3110(3) 0.0164(5) Uani 1 1 d . . .
N4 N 1.2597(2) 0.2986(2) 0.3031(3) 0.0291(6) Uani 1 1 d . . .
N5 N 0.8518(2) 0.4660(2) 0.3588(3) 0.0167(5) Uani 1 1 d . . .
N6 N 0.7432(2) 0.49297(19) 0.3817(3) 0.0156(5) Uani 1 1 d . . .
N7 N 0.6411(2) 0.5174(2) 0.4040(3) 0.0291(6) Uani 1 1 d . . .
N8 N 1.0345(2) 0.37617(19) -0.0426(3) 0.0151(5) Uani 1 1 d . . .
N9 N 0.9901(2) 0.34300(19) -0.1704(3) 0.0136(4) Uani 1 1 d . . .
N10 N 0.9507(2) 0.3117(2) -0.2984(3) 0.0203(5) Uani 1 1 d . . .
C1 C 0.7181(2) 0.4588(2) -0.0502(3) 0.0171(5) Uani 1 1 d . . .
H1A H 0.7634 0.5269 -0.0557 0.021 Uiso 1 1 calc R . .
C2 C 0.6050(3) 0.4510(3) -0.1358(3) 0.0211(6) Uani 1 1 d . . .
H2A H 0.5761 0.5120 -0.2004 0.025 Uiso 1 1 calc R . .
C3 C 0.5356(3) 0.3511(3) -0.1237(3) 0.0217(6) Uani 1 1 d . . .
H3A H 0.4589 0.3442 -0.1789 0.026 Uiso 1 1 calc R . .
C4 C 0.5822(3) 0.2616(3) -0.0281(4) 0.0224(6) Uani 1 1 d . . .
H4A H 0.5367 0.1939 -0.0168 0.027 Uiso 1 1 calc R . .
C5 C 0.6974(3) 0.2741(2) 0.0502(3) 0.0188(6) Uani 1 1 d . . .
H5B H 0.7294 0.2129 0.1119 0.023 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01215(18) 0.0183(2) 0.00963(16) -0.00210(11) -0.00151(12) -0.00007(12)
Cu2 0.0119(2) 0.0211(3) 0.0109(2) -0.00473(17) -0.00211(16) 0.00232(17)
N1 0.0116(10) 0.0197(12) 0.0115(10) -0.0019(9) -0.0009(8) -0.0019(9)
N2 0.0133(11) 0.0181(12) 0.0127(10) -0.0040(9) -0.0039(8) 0.0033(9)
N3 0.0162(11) 0.0190(12) 0.0140(10) -0.0007(9) -0.0004(9) -0.0001(10)
N4 0.0198(13) 0.0281(15) 0.0395(15) -0.0008(12) 0.0029(11) 0.0072(11)
N5 0.0127(11) 0.0258(12) 0.0117(10) -0.0055(9) -0.0003(8) 0.0008(10)
N6 0.0145(12) 0.0191(12) 0.0131(10) 0.0000(8) -0.0017(9) 0.0000(9)
N7 0.0174(13) 0.0382(16) 0.0317(14) -0.0019(12) -0.0004(10) 0.0041(11)
N8 0.0153(11) 0.0191(12) 0.0108(10) -0.0030(8) 0.0010(8) -0.0020(9)
N9 0.0153(11) 0.0107(11) 0.0148(10) 0.0012(8) 0.0010(8) 0.0009(9)
N10 0.0266(12) 0.0207(12) 0.0135(10) -0.0046(9) -0.0067(9) 0.0015(10)
C1 0.0148(12) 0.0202(14) 0.0164(12) 0.0028(11) -0.0010(10) -0.0039(11)
C2 0.0180(13) 0.0243(16) 0.0208(13) 0.0030(11) -0.0026(11) 0.0005(12)
C3 0.0164(13) 0.0278(16) 0.0209(13) -0.0027(12) -0.0044(11) -0.0002(12)
C4 0.0190(13) 0.0224(15) 0.0258(14) -0.0030(12) 0.0000(11) -0.0048(12)
C5 0.0205(13) 0.0166(14) 0.0194(13) 0.0009(11) -0.0004(11) 0.0006(11)

_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 1.995(2) . ?
Cu1 N8 1.995(2) . ?
Cu1 N5 2.014(2) . ?
Cu1 N2 2.025(2) . ?
Cu1 N10 2.384(2) 4_566 ?
Cu2 N5 1.975(2) 3_766 ?
Cu2 N5 1.975(2) . ?
Cu2 N2 1.989(2) . ?
Cu2 N2 1.989(2) 3_766 ?
N1 C5 1.342(3) . ?
N1 C1 1.349(3) . ?
N2 N3 1.220(3) . ?
N3 N4 1.139(3) . ?
N5 N6 1.216(3) . ?
N6 N7 1.142(3) . ?
N8 N9 1.191(3) . ?
N9 N10 1.165(3) . ?
N10 Cu1 2.384(2) 4_565 ?
C1 C2 1.384(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4A 0.9300 . ?
C5 H5B 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 95.77(9) . . ?
N1 Cu1 N5 93.67(9) . . ?
N8 Cu1 N5 157.54(9) . . ?
N1 Cu1 N2 170.45(9) . . ?
N8 Cu1 N2 93.76(9) . . ?
N5 Cu1 N2 77.16(9) . . ?
N1 Cu1 N10 92.34(9) . 4_566 ?
N8 Cu1 N10 88.88(9) . 4_566 ?
N5 Cu1 N10 111.07(9) . 4_566 ?
N2 Cu1 N10 88.54(9) . 4_566 ?
N5 Cu2 N5 180.0 3_766 . ?
N5 Cu2 N2 101.09(9) 3_766 . ?
N5 Cu2 N2 78.91(9) . . ?
N5 Cu2 N2 78.91(9) 3_766 3_766 ?
N5 Cu2 N2 101.09(9) . 3_766 ?
N2 Cu2 N2 180.000(1) . 3_766 ?
C5 N1 C1 118.1(2) . . ?
C5 N1 Cu1 122.37(18) . . ?
C1 N1 Cu1 119.53(18) . . ?
N3 N2 Cu2 130.99(18) . . ?
N3 N2 Cu1 123.00(18) . . ?
Cu2 N2 Cu1 101.35(9) . . ?
N4 N3 N2 178.0(3) . . ?
N6 N5 Cu2 128.17(18) . . ?
N6 N5 Cu1 129.34(18) . . ?
Cu2 N5 Cu1 102.24(10) . . ?
N7 N6 N5 179.3(3) . . ?
N9 N8 Cu1 120.49(19) . . ?
N10 N9 N8 177.4(3) . . ?
N9 N10 Cu1 117.76(18) . 4_565 ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 C4 122.6(3) . . ?
N1 C5 H5B 118.7 . . ?
C4 C5 H5B 118.7 . . ?

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
N8 Cu1 N1 C5 106.1(2) . . . . ?
N5 Cu1 N1 C5 -94.3(2) . . . . ?
N2 Cu1 N1 C5 -78.2(6) . . . . ?
N10 Cu1 N1 C5 17.0(2) 4_566 . . . ?
N8 Cu1 N1 C1 -75.2(2) . . . . ?
N5 Cu1 N1 C1 84.4(2) . . . . ?
N2 Cu1 N1 C1 100.5(6) . . . . ?
N10 Cu1 N1 C1 -164.3(2) 4_566 . . . ?
N5 Cu2 N2 N3 28.9(3) 3_766 . . . ?
N5 Cu2 N2 N3 -151.1(3) . . . . ?
N2 Cu2 N2 N3 -164(100) 3_766 . . . ?
N5 Cu2 N2 Cu1 -175.56(9) 3_766 . . . ?
N5 Cu2 N2 Cu1 4.44(9) . . . . ?
N2 Cu2 N2 Cu1 -8(100) 3_766 . . . ?
N1 Cu1 N2 N3 137.2(5) . . . . ?
N8 Cu1 N2 N3 -47.0(2) . . . . ?
N5 Cu1 N2 N3 153.8(2) . . . . ?
N10 Cu1 N2 N3 41.8(2) 4_566 . . . ?
N1 Cu1 N2 Cu2 -20.9(6) . . . . ?
N8 Cu1 N2 Cu2 154.83(10) . . . . ?
N5 Cu1 N2 Cu2 -4.38(9) . . . . ?
N10 Cu1 N2 Cu2 -116.39(10) 4_566 . . . ?
Cu2 N2 N3 N4 -153(8) . . . . ?
Cu1 N2 N3 N4 56(8) . . . . ?
N5 Cu2 N5 N6 -22(100) 3_766 . . . ?
N2 Cu2 N5 N6 -179.1(3) . . . . ?
N2 Cu2 N5 N6 0.9(3) 3_766 . . . ?
N5 Cu2 N5 Cu1 152(100) 3_766 . . . ?
N2 Cu2 N5 Cu1 -4.48(10) . . . . ?
N2 Cu2 N5 Cu1 175.52(10) 3_766 . . . ?
N1 Cu1 N5 N6 -3.7(3) . . . . ?
N8 Cu1 N5 N6 111.0(3) . . . . ?
N2 Cu1 N5 N6 179.0(3) . . . . ?
N10 Cu1 N5 N6 -97.6(3) 4_566 . . . ?
N1 Cu1 N5 Cu2 -178.28(10) . . . . ?
N8 Cu1 N5 Cu2 -63.5(3) . . . . ?
N2 Cu1 N5 Cu2 4.43(9) . . . . ?
N10 Cu1 N5 Cu2 87.79(11) 4_566 . . . ?
Cu2 N5 N6 N7 -88(28) . . . . ?
Cu1 N5 N6 N7 99(28) . . . . ?
N1 Cu1 N8 N9 -12.3(2) . . . . ?
N5 Cu1 N8 N9 -126.7(2) . . . . ?
N2 Cu1 N8 N9 168.4(2) . . . . ?
N10 Cu1 N8 N9 79.9(2) 4_566 . . . ?
Cu1 N8 N9 N10 170(6) . . . . ?
N8 N9 N10 Cu1 109(6) . . . 4_565 ?
C5 N1 C1 C2 -1.3(4) . . . . ?
Cu1 N1 C1 C2 179.9(2) . . . . ?
N1 C1 C2 C3 2.0(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
Cu1 N1 C5 C4 178.2(2) . . . . ?
C3 C4 C5 N1 1.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.93
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1418683'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cu3 N26'
_chemical_formula_sum            'C12 H12 Cu3 N26'
_chemical_formula_weight         711.10

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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.274(3)
_cell_length_b                   11.452(2)
_cell_length_c                   7.8834(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.76(3)
_cell_angle_gamma                90.00
_cell_volume                     1246.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2652
_cell_measurement_theta_min      2.3107
_cell_measurement_theta_max      27.8804

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            'Dark green'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             706
_exptl_absorpt_coefficient_mu    2.599
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8245
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9200
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2255
_reflns_number_gt                1924
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        "CrystalStructure (Rigaku/MSC'2004)"
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1019P)²+0.9931P] 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     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1874
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.93972(6) 0.91230(7) 0.12011(10) 0.0257(4) Uani 1 1 d . . .
Cu2 Cu 1.0000 1.0000 0.5000 0.0262(4) Uani 1 2 d S . .
N1 N 0.8127(4) 0.9065(5) -0.0591(7) 0.0317(15) Uani 1 1 d . . .
N2 N 1.0573(4) 0.9203(5) 0.3263(7) 0.0251(13) Uani 1 1 d . . .
N3 N 1.1239(4) 0.8506(5) 0.3547(7) 0.0310(14) Uani 1 1 d . . .
N4 N 1.1863(4) 0.7869(5) 0.3769(9) 0.0368(15) Uani 1 1 d . . .
N5 N 0.8826(4) 0.9824(5) 0.3066(8) 0.0290(13) Uani 1 1 d . . .
N6 N 0.7993(4) 0.9993(5) 0.3064(8) 0.0331(15) Uani 1 1 d . . .
N7 N 0.7190(5) 1.0124(8) 0.3039(11) 0.061(2) Uani 1 1 d . . .
N8 N 1.0172(4) 0.8764(6) -0.0500(7) 0.0287(13) Uani 1 1 d . . .
N9 N 0.9812(4) 0.8397(5) -0.1895(7) 0.0284(13) Uani 1 1 d . . .
N10 N 0.9473(5) 0.8041(6) -0.3303(8) 0.0353(15) Uani 1 1 d . . .
N11 N 0.5243(6) 1.1105(10) -0.2816(13) 0.078(3) Uani 1 1 d . . .
N12 N 0.5199(6) 1.1236(8) -0.1302(16) 0.063(2) Uani 1 1 d . . .
N13 N 0.5070(8) 1.1352(11) 0.0068(17) 0.092(4) Uani 1 1 d . . .
C1 C 0.7784(6) 0.8047(8) -0.1316(9) 0.042(2) Uani 1 1 d . . .
H1A H 0.8124 0.7364 -0.0931 0.051 Uiso 1 1 calc R . .
C2 C 0.6925(6) 0.7991(9) -0.2641(11) 0.054(2) Uani 1 1 d . . .
H2A H 0.6694 0.7277 -0.3140 0.064 Uiso 1 1 calc R . .
C3 C 0.6436(6) 0.8979(9) -0.3187(12) 0.054(3) Uani 1 1 d . . .
H3A H 0.5862 0.8950 -0.4069 0.065 Uiso 1 1 calc R . .
C4 C 0.6784(6) 1.0055(8) -0.2433(11) 0.046(2) Uani 1 1 d . . .
C5 C 0.7629(5) 1.0032(7) -0.1122(10) 0.0337(18) Uani 1 1 d . . .
H5A H 0.7864 1.0732 -0.0579 0.040 Uiso 1 1 calc R . .
C6 C 0.6240(6) 1.1172(10) -0.3003(13) 0.058(3) Uani 1 1 d . . .
H6A H 0.6576 1.1814 -0.2300 0.069 Uiso 1 1 calc R . .
H6B H 0.6226 1.1328 -0.4219 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0258(5) 0.0372(6) 0.0145(5) -0.0012(3) 0.0056(3) 0.0003(3)
Cu2 0.0259(7) 0.0377(8) 0.0150(6) -0.0010(4) 0.0054(5) 0.0033(4)
N1 0.033(3) 0.046(4) 0.016(3) 0.002(2) 0.006(2) -0.002(3)
N2 0.024(3) 0.032(3) 0.019(3) -0.002(2) 0.006(2) 0.005(2)
N3 0.037(4) 0.037(4) 0.021(3) 0.003(3) 0.011(2) -0.005(3)
N4 0.029(3) 0.037(4) 0.047(4) 0.007(3) 0.015(3) 0.006(3)
N5 0.029(3) 0.039(4) 0.019(3) -0.003(2) 0.006(2) -0.004(2)
N6 0.026(3) 0.051(4) 0.022(3) -0.002(3) 0.005(2) -0.005(2)
N7 0.028(4) 0.101(7) 0.056(5) -0.012(4) 0.013(3) 0.011(4)
N8 0.032(3) 0.041(3) 0.015(3) -0.002(3) 0.010(2) -0.005(3)
N9 0.032(3) 0.034(3) 0.022(3) 0.005(3) 0.011(2) 0.010(2)
N10 0.044(3) 0.040(4) 0.022(3) 0.000(3) 0.009(3) 0.006(3)
N11 0.047(5) 0.125(9) 0.064(6) 0.046(6) 0.016(4) 0.017(5)
N12 0.041(4) 0.057(5) 0.094(8) 0.021(5) 0.022(5) 0.022(4)
N13 0.082(7) 0.084(9) 0.126(11) -0.006(7) 0.057(7) 0.014(5)
C1 0.036(4) 0.064(6) 0.028(4) -0.006(4) 0.009(3) -0.002(3)
C2 0.039(4) 0.079(7) 0.039(5) -0.015(5) 0.003(4) -0.017(4)
C3 0.027(4) 0.084(7) 0.039(5) 0.003(5) -0.011(4) -0.001(4)
C4 0.031(4) 0.072(6) 0.034(4) 0.014(4) 0.008(3) 0.009(4)
C5 0.023(3) 0.054(5) 0.025(4) 0.009(3) 0.007(3) -0.003(3)
C6 0.029(4) 0.082(7) 0.057(6) 0.025(5) 0.002(4) 0.007(4)

_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 N8 1.986(6) . ?
Cu1 N1 1.995(6) . ?
Cu1 N2 2.019(6) . ?
Cu1 N5 2.020(6) . ?
Cu2 N5 1.967(6) . ?
Cu2 N5 1.967(6) 3_776 ?
Cu2 N2 1.987(6) . ?
Cu2 N2 1.987(6) 3_776 ?
N1 C5 1.325(9) . ?
N1 C1 1.335(10) . ?
N2 N3 1.218(8) . ?
N3 N4 1.130(8) . ?
N5 N6 1.205(9) . ?
N6 N7 1.151(10) . ?
N8 N9 1.167(8) . ?
N9 N10 1.166(8) . ?
N11 N12 1.220(14) . ?
N11 C6 1.470(13) . ?
N12 N13 1.149(13) . ?
C1 C2 1.396(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.342(14) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(11) . ?
C4 C6 1.504(13) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
N8 Cu1 N1 94.4(2) . . ?
N8 Cu1 N2 93.5(2) . . ?
N1 Cu1 N2 172.0(2) . . ?
N8 Cu1 N5 166.1(2) . . ?
N1 Cu1 N5 93.8(2) . . ?
N2 Cu1 N5 78.6(2) . . ?
N5 Cu2 N5 180.000(1) . 3_776 ?
N5 Cu2 N2 80.7(2) . . ?
N5 Cu2 N2 99.3(2) 3_776 . ?
N5 Cu2 N2 99.3(2) . 3_776 ?
N5 Cu2 N2 80.7(2) 3_776 3_776 ?
N2 Cu2 N2 180.000(1) . 3_776 ?
C5 N1 C1 119.1(7) . . ?
C5 N1 Cu1 120.9(5) . . ?
C1 N1 Cu1 120.0(5) . . ?
N3 N2 Cu2 127.9(5) . . ?
N3 N2 Cu1 124.6(5) . . ?
Cu2 N2 Cu1 99.9(2) . . ?
N4 N3 N2 178.1(7) . . ?
N6 N5 Cu2 129.1(5) . . ?
N6 N5 Cu1 130.1(5) . . ?
Cu2 N5 Cu1 100.5(3) . . ?
N7 N6 N5 178.0(8) . . ?
N9 N8 Cu1 121.6(5) . . ?
N10 N9 N8 178.2(7) . . ?
N12 N11 C6 112.6(9) . . ?
N13 N12 N11 173.9(11) . . ?
N1 C1 C2 121.2(8) . . ?
N1 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 119.2(9) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C2 C3 C4 120.4(7) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 116.8(7) . . ?
C5 C4 C6 121.9(8) . . ?
C3 C4 C6 121.3(8) . . ?
N1 C5 C4 123.4(8) . . ?
N1 C5 H5A 118.3 . . ?
C4 C5 H5A 118.3 . . ?
N11 C6 C4 111.4(8) . . ?
N11 C6 H6A 109.3 . . ?
C4 C6 H6A 109.3 . . ?
N11 C6 H6B 109.3 . . ?
C4 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 Cu1 N1 C5 -108.1(6) . . . . ?
N2 Cu1 N1 C5 78.8(18) . . . . ?
N5 Cu1 N1 C5 60.7(6) . . . . ?
N8 Cu1 N1 C1 69.5(6) . . . . ?
N2 Cu1 N1 C1 -103.5(17) . . . . ?
N5 Cu1 N1 C1 -121.7(6) . . . . ?
N5 Cu2 N2 N3 -146.0(6) . . . . ?
N5 Cu2 N2 N3 34.0(6) 3_776 . . . ?
N2 Cu2 N2 N3 -114(100) 3_776 . . . ?
N5 Cu2 N2 Cu1 4.0(2) . . . . ?
N5 Cu2 N2 Cu1 -176.0(2) 3_776 . . . ?
N2 Cu2 N2 Cu1 36(100) 3_776 . . . ?
N8 Cu1 N2 N3 -44.1(6) . . . . ?
N1 Cu1 N2 N3 129.0(16) . . . . ?
N5 Cu1 N2 N3 147.4(6) . . . . ?
N8 Cu1 N2 Cu2 164.5(3) . . . . ?
N1 Cu1 N2 Cu2 -22.4(18) . . . . ?
N5 Cu1 N2 Cu2 -3.9(2) . . . . ?
Cu2 N2 N3 N4 -154(22) . . . . ?
Cu1 N2 N3 N4 62(23) . . . . ?
N5 Cu2 N5 N6 14(100) 3_776 . . . ?
N2 Cu2 N5 N6 170.1(7) . . . . ?
N2 Cu2 N5 N6 -9.9(7) 3_776 . . . ?
N5 Cu2 N5 Cu1 -160(100) 3_776 . . . ?
N2 Cu2 N5 Cu1 -4.0(2) . . . . ?
N2 Cu2 N5 Cu1 176.0(2) 3_776 . . . ?
N8 Cu1 N5 N6 133.6(9) . . . . ?
N1 Cu1 N5 N6 7.4(7) . . . . ?
N2 Cu1 N5 N6 -170.1(7) . . . . ?
N8 Cu1 N5 Cu2 -52.4(11) . . . . ?
N1 Cu1 N5 Cu2 -178.5(3) . . . . ?
N2 Cu1 N5 Cu2 4.0(2) . . . . ?
Cu2 N5 N6 N7 -133(24) . . . . ?
Cu1 N5 N6 N7 40(25) . . . . ?
N1 Cu1 N8 N9 -14.7(6) . . . . ?
N2 Cu1 N8 N9 164.3(6) . . . . ?
N5 Cu1 N8 N9 -140.8(9) . . . . ?
Cu1 N8 N9 N10 156(23) . . . . ?
C6 N11 N12 N13 177(11) . . . . ?
C5 N1 C1 C2 1.3(12) . . . . ?
Cu1 N1 C1 C2 -176.4(6) . . . . ?
N1 C1 C2 C3 -0.2(13) . . . . ?
C1 C2 C3 C4 0.0(15) . . . . ?
C2 C3 C4 C5 -0.8(14) . . . . ?
C2 C3 C4 C6 -179.0(9) . . . . ?
C1 N1 C5 C4 -2.2(12) . . . . ?
Cu1 N1 C5 C4 175.5(6) . . . . ?
C3 C4 C5 N1 1.9(12) . . . . ?
C6 C4 C5 N1 -179.9(8) . . . . ?
N12 N11 C6 C4 78.1(12) . . . . ?
C5 C4 C6 N11 -121.9(10) . . . . ?
C3 C4 C6 N11 56.3(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.160
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1418684'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cu N8 O2'
_chemical_formula_sum            'C24 H18 Cu N8 O2'
_chemical_formula_weight         514.00

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-p 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8316(8)
_cell_length_b                   8.6029(17)
_cell_length_c                   16.855(3)
_cell_angle_alpha                94.24(3)
_cell_angle_beta                 96.16(3)
_cell_angle_gamma                99.46(3)
_cell_volume                     542.49(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4486
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Needle
_exptl_crystal_colour            'Dark green'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             263
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_T_max  0.8845
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4895
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.48
_reflns_number_total             2007
_reflns_number_gt                1428
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        "CrystalStructure (Rigaku/MSC'2004)"
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0734P)²+0.9530P] 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         2007
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 1.0000 0.5000 0.0902(5) Uani 1 2 d S . .
C1 C 0.2881(14) 0.9200(5) 0.3265(3) 0.0558(13) Uani 1 1 d . . .
H1A H 0.2313 1.0211 0.3295 0.067 Uiso 1 1 calc R . .
C2 C 0.2491(12) 0.8356(5) 0.2528(3) 0.0450(11) Uani 1 1 d . . .
H2A H 0.1674 0.8793 0.2070 0.054 Uiso 1 1 calc R . .
C3 C 0.3325(11) 0.6847(5) 0.2473(2) 0.0377(9) Uani 1 1 d . . .
C4 C 0.4462(12) 0.6242(5) 0.3173(2) 0.0444(10) Uani 1 1 d . . .
H4A H 0.4997 0.5225 0.3161 0.053 Uiso 1 1 calc R . .
C5 C 0.4793(14) 0.7169(5) 0.3891(3) 0.0534(12) Uani 1 1 d . . .
H5A H 0.5573 0.6756 0.4360 0.064 Uiso 1 1 calc R . .
C6 C 0.3189(10) 0.5996(5) 0.1649(2) 0.0362(9) Uani 1 1 d . . .
C7 C 0.1416(10) 0.4310(4) 0.1469(2) 0.0348(9) Uani 1 1 d . . .
C8 C 0.1365(11) 0.3591(5) 0.0697(2) 0.0430(10) Uani 1 1 d . . .
H8A H 0.2431 0.4163 0.0314 0.052 Uiso 1 1 calc R . .
C9 C -0.0253(13) 0.2043(6) 0.0502(3) 0.0532(12) Uani 1 1 d . . .
H9A H -0.0278 0.1570 -0.0014 0.064 Uiso 1 1 calc R . .
C10 C -0.1847(12) 0.1184(5) 0.1070(3) 0.0557(13) Uani 1 1 d . . .
H10A H -0.2910 0.0131 0.0939 0.067 Uiso 1 1 calc R . .
C11 C -0.1854(12) 0.1885(5) 0.1823(3) 0.0509(12) Uani 1 1 d . . .
H11A H -0.2948 0.1308 0.2202 0.061 Uiso 1 1 calc R . .
C12 C -0.0248(11) 0.3447(5) 0.2029(3) 0.0408(10) Uani 1 1 d . . .
H12A H -0.0286 0.3918 0.2542 0.049 Uiso 1 1 calc R . .
N1 N 0.4041(12) 0.8632(4) 0.3941(2) 0.0578(11) Uani 1 1 d . . .
N2 N 0.9163(15) 1.1379(6) 0.4571(3) 0.0759(14) Uani 1 1 d . . .
N3 N 0.8690(14) 1.2462(6) 0.4298(3) 0.0732(14) Uani 1 1 d . . .
N4 N 0.837(3) 1.3618(12) 0.4038(6) 0.183(5) Uani 1 1 d . . .
O1 O 0.4524(10) 0.6750(4) 0.11457(18) 0.0596(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.1725(12) 0.0424(5) 0.0412(5) -0.0177(4) 0.0374(6) -0.0298(6)
C1 0.089(4) 0.029(2) 0.049(3) -0.0030(19) 0.023(3) 0.005(2)
C2 0.059(3) 0.033(2) 0.042(2) 0.0013(17) 0.013(2) 0.002(2)
C3 0.039(2) 0.035(2) 0.036(2) -0.0041(16) 0.0104(17) -0.0049(17)
C4 0.056(3) 0.035(2) 0.039(2) -0.0039(17) 0.005(2) 0.002(2)
C5 0.076(3) 0.041(3) 0.036(2) 0.0006(19) 0.005(2) -0.006(2)
C6 0.035(2) 0.039(2) 0.034(2) -0.0026(17) 0.0060(17) 0.0052(18)
C7 0.030(2) 0.035(2) 0.039(2) -0.0057(16) 0.0023(17) 0.0085(17)
C8 0.043(2) 0.046(2) 0.038(2) -0.0086(18) 0.0037(19) 0.008(2)
C9 0.054(3) 0.051(3) 0.051(3) -0.022(2) -0.009(2) 0.022(2)
C10 0.044(3) 0.032(2) 0.084(4) -0.015(2) -0.004(3) 0.002(2)
C11 0.042(3) 0.038(2) 0.071(3) 0.000(2) 0.012(2) 0.001(2)
C12 0.038(2) 0.038(2) 0.046(2) -0.0063(18) 0.0097(19) 0.0063(18)
N1 0.092(3) 0.037(2) 0.039(2) -0.0088(16) 0.020(2) -0.006(2)
N2 0.114(4) 0.054(3) 0.056(3) -0.012(2) 0.017(3) 0.007(3)
N3 0.118(4) 0.061(3) 0.050(2) 0.031(2) 0.018(3) 0.026(3)
N4 0.201(9) 0.177(8) 0.231(10) 0.148(8) 0.112(8) 0.099(7)
O1 0.084(2) 0.0501(19) 0.0398(16) -0.0036(14) 0.0232(16) -0.0107(17)

_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 2.027(3) 2_676 ?
Cu1 N1 2.027(3) . ?
Cu1 N2 2.056(5) 2_676 ?
Cu1 N2 2.056(5) . ?
C1 N1 1.334(6) . ?
C1 C2 1.373(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.386(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(6) . ?
C3 C6 1.513(5) . ?
C4 C5 1.381(6) . ?
C4 H4A 0.9300 . ?
C5 N1 1.336(6) . ?
C5 H5A 0.9300 . ?
C6 O1 1.211(5) . ?
C6 C7 1.491(5) . ?
C7 C12 1.387(6) . ?
C7 C8 1.395(5) . ?
C8 C9 1.373(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.385(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.364(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
N2 N3 1.101(6) . ?
N3 N4 1.136(8) . ?

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 N1 180.000(2) 2_676 . ?
N1 Cu1 N2 89.19(16) 2_676 2_676 ?
N1 Cu1 N2 90.81(16) . 2_676 ?
N1 Cu1 N2 90.81(16) 2_676 . ?
N1 Cu1 N2 89.19(16) . . ?
N2 Cu1 N2 180.000(1) 2_676 . ?
N1 C1 C2 122.8(4) . . ?
N1 C1 H1A 118.6 . . ?
C2 C1 H1A 118.6 . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 C6 123.4(4) . . ?
C2 C3 C6 118.5(4) . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
O1 C6 C7 122.0(3) . . ?
O1 C6 C3 117.1(3) . . ?
C7 C6 C3 120.8(3) . . ?
C12 C7 C8 119.0(4) . . ?
C12 C7 C6 122.8(3) . . ?
C8 C7 C6 118.2(4) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C7 120.0(4) . . ?
C11 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
C1 N1 C5 117.9(4) . . ?
C1 N1 Cu1 121.2(3) . . ?
C5 N1 Cu1 120.7(3) . . ?
N3 N2 Cu1 118.9(5) . . ?
N2 N3 N4 176.4(9) . . ?

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
N1 C1 C2 C3 0.0(7) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 C6 -174.7(4) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C6 C3 C4 C5 174.3(4) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
C4 C3 C6 O1 -130.9(5) . . . . ?
C2 C3 C6 O1 44.8(6) . . . . ?
C4 C3 C6 C7 50.3(6) . . . . ?
C2 C3 C6 C7 -134.0(4) . . . . ?
O1 C6 C7 C12 -177.4(4) . . . . ?
C3 C6 C7 C12 1.4(6) . . . . ?
O1 C6 C7 C8 1.0(6) . . . . ?
C3 C6 C7 C8 179.8(4) . . . . ?
C12 C7 C8 C9 -1.2(6) . . . . ?
C6 C7 C8 C9 -179.7(4) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C11 0.9(7) . . . . ?
C9 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C7 -0.6(7) . . . . ?
C8 C7 C12 C11 1.5(6) . . . . ?
C6 C7 C12 C11 179.9(4) . . . . ?
C2 C1 N1 C5 -1.0(7) . . . . ?
C2 C1 N1 Cu1 174.3(4) . . . . ?
C4 C5 N1 C1 0.8(7) . . . . ?
C4 C5 N1 Cu1 -174.5(3) . . . . ?
N1 Cu1 N1 C1 -44(100) 2_676 . . . ?
N2 Cu1 N1 C1 113.1(4) 2_676 . . . ?
N2 Cu1 N1 C1 -66.9(4) . . . . ?
N1 Cu1 N1 C5 131(100) 2_676 . . . ?
N2 Cu1 N1 C5 -71.7(4) 2_676 . . . ?
N2 Cu1 N1 C5 108.3(4) . . . . ?
N1 Cu1 N2 N3 -84.9(5) 2_676 . . . ?
N1 Cu1 N2 N3 95.1(5) . . . . ?
N2 Cu1 N2 N3 73(100) 2_676 . . . ?
Cu1 N2 N3 N4 137(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.981
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1418685'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 Cu N7 O0'
_chemical_formula_sum            'C9 H7 Cu N7 O0'
_chemical_formula_weight         276.76

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.722(3)
_cell_length_b                   14.935(3)
_cell_length_c                   5.7789(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1096.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5807
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.54

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    1.980
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8541
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1988
_reflns_number_gt                1345
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        "CrystalStructure (Rigaku/MSC'2004)"
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+1.2592P] 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         1988
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.77047(5) 0.29571(5) 0.23250(11) 0.0456(3) Uani 1 1 d . . .
N1 N 0.7331(5) 0.4245(4) 0.1535(11) 0.0723(16) Uani 1 1 d . . .
N2 N 0.6735(4) 0.2130(4) -0.0143(9) 0.0563(14) Uani 1 1 d . . .
N3 N 0.5893(5) 0.1851(4) -0.0232(10) 0.0702(18) Uani 1 1 d . . .
N4 N 0.5058(7) 0.1576(9) -0.0224(18) 0.169(5) Uani 1 1 d . . .
N5 N 0.8627(4) 0.2790(4) -0.0297(8) 0.0509(13) Uani 1 1 d . . .
N6 N 0.9387(5) 0.3192(4) -0.0628(9) 0.0620(15) Uani 1 1 d . . .
N7 N 1.0139(6) 0.3597(6) -0.0993(14) 0.126(3) Uani 1 1 d . . .
C1 C 0.6661(6) 0.4433(6) -0.0235(13) 0.081(2) Uani 1 1 d . . .
H1A H 0.6438 0.3955 -0.1173 0.098 Uiso 1 1 calc R . .
C2 C 0.6262(7) 0.5258(7) -0.0830(17) 0.093(3) Uani 1 1 d . . .
H2A H 0.5811 0.5330 -0.2142 0.112 Uiso 1 1 calc R . .
C3 C 0.6545(8) 0.5978(8) 0.056(2) 0.109(4) Uani 1 1 d . . .
H3A H 0.6275 0.6547 0.0251 0.130 Uiso 1 1 calc R . .
C4 C 0.7307(6) 0.5803(5) 0.2585(15) 0.078(2) Uani 1 1 d . . .
C5 C 0.7628(10) 0.6495(7) 0.404(3) 0.126(4) Uani 1 1 d . . .
H5A H 0.7368 0.7074 0.3844 0.152 Uiso 1 1 calc R . .
C6 C 0.8347(10) 0.6282(10) 0.578(2) 0.132(4) Uani 1 1 d . . .
H6A H 0.8601 0.6735 0.6763 0.158 Uiso 1 1 calc R . .
C7 C 0.8713(7) 0.5434(7) 0.6152(17) 0.095(3) Uani 1 1 d . . .
H7A H 0.9200 0.5331 0.7388 0.114 Uiso 1 1 calc R . .
C8 C 0.8398(6) 0.4740(6) 0.4801(13) 0.080(2) Uani 1 1 d . . .
H8A H 0.8654 0.4164 0.5085 0.096 Uiso 1 1 calc R . .
C9 C 0.7640(5) 0.4927(5) 0.2872(13) 0.0646(19) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0546(5) 0.0528(5) 0.0298(5) 0.0030(3) 0.0047(3) 0.0034(3)
N1 0.085(4) 0.069(4) 0.065(4) 0.003(3) 0.019(3) -0.001(3)
N2 0.066(3) 0.074(4) 0.031(3) -0.012(2) 0.010(2) -0.016(3)
N3 0.066(4) 0.093(5) 0.052(4) -0.024(3) 0.008(3) -0.021(3)
N4 0.098(6) 0.280(13) 0.134(8) -0.090(8) 0.037(5) -0.094(8)
N5 0.058(3) 0.063(4) 0.032(3) -0.002(2) 0.005(2) -0.010(2)
N6 0.063(4) 0.083(4) 0.040(3) -0.012(3) 0.001(2) -0.007(3)
N7 0.095(5) 0.176(9) 0.111(6) -0.039(6) 0.036(4) -0.072(6)
C1 0.073(5) 0.108(7) 0.062(5) 0.026(5) -0.005(4) 0.022(4)
C2 0.083(5) 0.102(8) 0.095(7) 0.033(6) 0.009(5) 0.022(5)
C3 0.101(7) 0.096(8) 0.135(10) 0.045(7) 0.057(7) 0.022(6)
C4 0.087(5) 0.051(5) 0.100(7) 0.000(4) 0.042(5) -0.001(4)
C5 0.137(9) 0.054(6) 0.197(13) -0.015(7) 0.091(9) -0.009(6)
C6 0.105(8) 0.143(13) 0.149(12) -0.024(9) 0.024(8) -0.026(8)
C7 0.094(6) 0.089(7) 0.104(7) -0.028(6) 0.013(5) -0.018(5)
C8 0.076(5) 0.101(7) 0.064(5) -0.014(5) 0.012(4) -0.020(4)
C9 0.066(4) 0.053(4) 0.079(5) -0.003(4) 0.032(4) -0.002(3)

_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 N2 1.973(5) 4_566 ?
Cu1 N5 1.986(5) . ?
Cu1 N1 2.027(7) . ?
Cu1 N5 2.078(5) 4_566 ?
Cu1 N2 2.208(5) . ?
N1 C1 1.322(9) . ?
N1 C9 1.324(9) . ?
N2 N3 1.148(7) . ?
N2 Cu1 1.973(5) 4_565 ?
N3 N4 1.139(9) . ?
N5 N6 1.164(7) . ?
N5 Cu1 2.078(5) 4_565 ?
N6 N7 1.162(8) . ?
C1 C2 1.368(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.377(13) . ?
C2 H2A 0.9300 . ?
C3 C4 1.499(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(14) . ?
C4 C9 1.382(10) . ?
C5 C6 1.355(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.362(15) . ?
C6 H6A 0.9300 . ?
C7 C8 1.345(11) . ?
C7 H7A 0.9300 . ?
C8 C9 1.457(10) . ?
C8 H8A 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
N2 Cu1 N5 168.7(2) 4_566 . ?
N2 Cu1 N1 94.6(2) 4_566 . ?
N5 Cu1 N1 95.1(2) . . ?
N2 Cu1 N5 80.1(2) 4_566 4_566 ?
N5 Cu1 N5 95.8(2) . 4_566 ?
N1 Cu1 N5 140.7(2) . 4_566 ?
N2 Cu1 N2 95.3(2) 4_566 . ?
N5 Cu1 N2 76.67(19) . . ?
N1 Cu1 N2 105.7(2) . . ?
N5 Cu1 N2 113.5(2) 4_566 . ?
C1 N1 C9 116.4(8) . . ?
C1 N1 Cu1 120.5(6) . . ?
C9 N1 Cu1 122.7(6) . . ?
N3 N2 Cu1 124.4(5) . 4_565 ?
N3 N2 Cu1 135.8(5) . . ?
Cu1 N2 Cu1 99.6(2) 4_565 . ?
N4 N3 N2 177.2(8) . . ?
N6 N5 Cu1 126.4(5) . . ?
N6 N5 Cu1 127.6(4) . 4_565 ?
Cu1 N5 Cu1 103.7(2) . 4_565 ?
N7 N6 N5 178.9(8) . . ?
N1 C1 C2 126.7(9) . . ?
N1 C1 H1A 116.6 . . ?
C2 C1 H1A 116.6 . . ?
C1 C2 C3 118.5(9) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 116.9(9) . . ?
C2 C3 H3A 121.5 . . ?
C4 C3 H3A 121.5 . . ?
C5 C4 C9 123.9(10) . . ?
C5 C4 C3 120.0(10) . . ?
C9 C4 C3 116.0(8) . . ?
C6 C5 C4 116.0(11) . . ?
C6 C5 H5A 122.0 . . ?
C4 C5 H5A 122.0 . . ?
C5 C6 C7 123.0(12) . . ?
C5 C6 H6A 118.5 . . ?
C7 C6 H6A 118.5 . . ?
C8 C7 C6 122.5(11) . . ?
C8 C7 H7A 118.7 . . ?
C6 C7 H7A 118.7 . . ?
C7 C8 C9 117.2(9) . . ?
C7 C8 H8A 121.4 . . ?
C9 C8 H8A 121.4 . . ?
N1 C9 C4 125.4(8) . . ?
N1 C9 C8 117.3(7) . . ?
C4 C9 C8 117.3(8) . . ?

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
N2 Cu1 N1 C1 -99.7(6) 4_566 . . . ?
N5 Cu1 N1 C1 74.7(6) . . . . ?
N5 Cu1 N1 C1 -179.6(5) 4_566 . . . ?
N2 Cu1 N1 C1 -2.9(6) . . . . ?
N2 Cu1 N1 C9 72.8(5) 4_566 . . . ?
N5 Cu1 N1 C9 -112.8(5) . . . . ?
N5 Cu1 N1 C9 -7.2(7) 4_566 . . . ?
N2 Cu1 N1 C9 169.6(5) . . . . ?
N2 Cu1 N2 N3 11.9(7) 4_566 . . . ?
N5 Cu1 N2 N3 -176.1(8) . . . . ?
N1 Cu1 N2 N3 -84.5(8) . . . . ?
N5 Cu1 N2 N3 93.3(8) 4_566 . . . ?
N2 Cu1 N2 Cu1 -173.7(3) 4_566 . . 4_565 ?
N5 Cu1 N2 Cu1 -1.6(2) . . . 4_565 ?
N1 Cu1 N2 Cu1 90.0(3) . . . 4_565 ?
N5 Cu1 N2 Cu1 -92.2(2) 4_566 . . 4_565 ?
Cu1 N2 N3 N4 163(21) 4_565 . . . ?
Cu1 N2 N3 N4 -23(22) . . . . ?
N2 Cu1 N5 N6 -149.5(9) 4_566 . . . ?
N1 Cu1 N5 N6 60.6(6) . . . . ?
N5 Cu1 N5 N6 -81.6(5) 4_566 . . . ?
N2 Cu1 N5 N6 165.5(6) . . . . ?
N2 Cu1 N5 Cu1 46.6(11) 4_566 . . 4_565 ?
N1 Cu1 N5 Cu1 -103.4(3) . . . 4_565 ?
N5 Cu1 N5 Cu1 114.4(3) 4_566 . . 4_565 ?
N2 Cu1 N5 Cu1 1.6(2) . . . 4_565 ?
Cu1 N5 N6 N7 -127(46) . . . . ?
Cu1 N5 N6 N7 33(47) 4_565 . . . ?
C9 N1 C1 C2 0.4(12) . . . . ?
Cu1 N1 C1 C2 173.3(6) . . . . ?
N1 C1 C2 C3 -2.1(13) . . . . ?
C1 C2 C3 C4 2.2(12) . . . . ?
C2 C3 C4 C5 179.7(8) . . . . ?
C2 C3 C4 C9 -0.8(11) . . . . ?
C9 C4 C5 C6 2.8(14) . . . . ?
C3 C4 C5 C6 -177.7(9) . . . . ?
C4 C5 C6 C7 -2.3(17) . . . . ?
C5 C6 C7 C8 0.8(18) . . . . ?
C6 C7 C8 C9 0.4(13) . . . . ?
C1 N1 C9 C4 1.2(10) . . . . ?
Cu1 N1 C9 C4 -171.5(5) . . . . ?
C1 N1 C9 C8 -178.5(6) . . . . ?
Cu1 N1 C9 C8 8.7(8) . . . . ?
C5 C4 C9 N1 178.5(7) . . . . ?
C3 C4 C9 N1 -1.0(11) . . . . ?
C5 C4 C9 C8 -1.7(11) . . . . ?
C3 C4 C9 C8 178.7(6) . . . . ?
C7 C8 C9 N1 179.8(7) . . . . ?
C7 C8 C9 C4 0.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.240
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.095


