# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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 1407348'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 Co N10 O16'
_chemical_formula_sum            'C18 H16 Co N10 O16'
_chemical_formula_weight         687.34

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'
Co Co 0.3494 0.9721 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.4175(7)
_cell_length_b                   9.9444(11)
_cell_length_c                   21.244(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.437(2)
_cell_angle_gamma                90.00
_cell_volume                     1355.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.89

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             698
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.8444
_exptl_absorpt_correction_T_max  0.9176
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         no
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  'no standards in IP'
_diffrn_standards_decay_%        no
_diffrn_reflns_number            7004
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.89
_reflns_number_total             2603
_reflns_number_gt                2066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0520P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2603
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.0000 0.02673(16) Uani 1 2 d S . .
O8 O 0.2673(3) 0.5894(2) 0.05509(10) 0.0361(4) Uani 1 1 d . . .
O1 O 1.1307(2) 0.84555(18) 0.02596(9) 0.0465(5) Uani 1 1 d . . .
N1 N 0.6652(3) 0.68099(19) -0.00616(9) 0.0321(5) Uani 1 1 d . . .
C2 C 0.9527(4) 0.8087(2) 0.00949(11) 0.0321(6) Uani 1 1 d . . .
N2 N 0.8675(3) 0.6860(2) 0.01616(11) 0.0414(6) Uani 1 1 d . . .
H2 H 0.9325 0.6185 0.0326 0.050 Uiso 1 1 calc R . .
N3 N 0.7975(3) 0.88191(19) -0.01887(9) 0.0315(5) Uani 1 1 d . . .
H4 H 0.8051 0.9649 -0.0299 0.038 Uiso 1 1 calc R . .
C1 C 0.6293(4) 0.8010(2) -0.02660(11) 0.0311(6) Uani 1 1 d . . .
C5 C 0.9641(4) 0.3480(3) 0.17543(12) 0.0365(6) Uani 1 1 d . . .
O3 O 0.9745(3) 0.4318(3) 0.40320(9) 0.0618(6) Uani 1 1 d . . .
N4 N 1.2831(4) 0.2305(3) 0.21261(12) 0.0518(6) Uani 1 1 d . . .
C8 C 0.8900(4) 0.4239(3) 0.29693(11) 0.0353(6) Uani 1 1 d . . .
O4 O 1.4132(3) 0.2176(3) 0.25473(11) 0.0751(7) Uani 1 1 d . . .
C9 C 0.6332(4) 0.4652(3) 0.13670(13) 0.0394(7) Uani 1 1 d . . .
C6 C 0.7887(4) 0.4233(3) 0.18788(11) 0.0337(6) Uani 1 1 d . . .
C7 C 0.7505(4) 0.4610(3) 0.24976(13) 0.0378(6) Uani 1 1 d . . .
C4 C 1.0970(4) 0.3123(3) 0.22477(12) 0.0357(6) Uani 1 1 d . . .
C3 C 1.0652(4) 0.3497(3) 0.28615(12) 0.0367(6) Uani 1 1 d . . .
N5 N 0.8533(4) 0.4684(3) 0.36186(11) 0.0492(6) Uani 1 1 d . . .
O6 O 0.4655(3) 0.5127(2) 0.15527(10) 0.0648(7) Uani 1 1 d . . .
O5 O 1.2979(4) 0.1807(3) 0.16075(11) 0.0856(9) Uani 1 1 d . . .
O7 O 0.6849(2) 0.44906(18) 0.08042(8) 0.0354(4) Uani 1 1 d . . .
O2 O 0.7071(4) 0.5411(3) 0.37116(11) 0.0911(9) Uani 1 1 d . . .
H8B H 0.265(6) 0.674(4) 0.0504(18) 0.098(15) Uiso 1 1 d . . .
H8A H 0.316(6) 0.577(4) 0.0914(19) 0.089(13) Uiso 1 1 d . . .
H7 H 0.641(4) 0.506(2) 0.2604(11) 0.024(6) Uiso 1 1 d . . .
H5 H 0.991(4) 0.320(3) 0.1343(13) 0.053(8) Uiso 1 1 d . . .
H3 H 1.157(4) 0.325(3) 0.3180(12) 0.039(7) Uiso 1 1 d . . .
H1 H 0.505(4) 0.831(2) -0.0435(11) 0.034(7) Uiso 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
Co1 N1 2.0946(18) 3_665 ?
Co1 N1 2.0946(18) . ?
Co1 O8 2.1162(19) . ?
Co1 O8 2.1162(19) 3_665 ?
Co1 O7 2.1169(16) . ?
Co1 O7 2.1169(16) 3_665 ?
O8 H8B 0.85(4) . ?
O8 H8A 0.83(4) . ?
O1 C2 1.242(3) . ?
N1 C1 1.289(3) . ?
N1 N2 1.372(2) . ?
C2 N2 1.346(3) . ?
C2 N3 1.362(3) . ?
N2 H2 0.8600 . ?
N3 C1 1.353(3) . ?
N3 H4 0.8600 . ?
C1 H1 0.92(2) . ?
C5 C4 1.381(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.94(3) . ?
O3 N5 1.214(3) . ?
N4 O5 1.214(3) . ?
N4 O4 1.215(3) . ?
N4 C4 1.473(3) . ?
C8 C3 1.369(3) . ?
C8 C7 1.377(3) . ?
C8 N5 1.473(3) . ?
C9 O6 1.248(3) . ?
C9 O7 1.259(3) . ?
C9 C6 1.516(3) . ?
C6 C7 1.394(4) . ?
C7 H7 0.87(2) . ?
C4 C3 1.376(4) . ?
C3 H3 0.92(2) . ?
N5 O2 1.205(3) . ?

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 Co1 N1 180.00(11) 3_665 . ?
N1 Co1 O8 87.76(8) 3_665 . ?
N1 Co1 O8 92.24(8) . . ?
N1 Co1 O8 92.24(8) 3_665 3_665 ?
N1 Co1 O8 87.76(8) . 3_665 ?
O8 Co1 O8 180.00(9) . 3_665 ?
N1 Co1 O7 91.05(7) 3_665 . ?
N1 Co1 O7 88.95(7) . . ?
O8 Co1 O7 92.48(7) . . ?
O8 Co1 O7 87.52(7) 3_665 . ?
N1 Co1 O7 88.95(7) 3_665 3_665 ?
N1 Co1 O7 91.05(7) . 3_665 ?
O8 Co1 O7 87.52(7) . 3_665 ?
O8 Co1 O7 92.48(7) 3_665 3_665 ?
O7 Co1 O7 180.0 . 3_665 ?
Co1 O8 H8B 111(3) . . ?
Co1 O8 H8A 101(3) . . ?
H8B O8 H8A 105(4) . . ?
C1 N1 N2 104.01(19) . . ?
C1 N1 Co1 136.92(16) . . ?
N2 N1 Co1 119.07(14) . . ?
O1 C2 N2 127.7(2) . . ?
O1 C2 N3 128.6(2) . . ?
N2 C2 N3 103.69(19) . . ?
C2 N2 N1 112.34(19) . . ?
C2 N2 H2 123.8 . . ?
N1 N2 H2 123.8 . . ?
C1 N3 C2 107.95(19) . . ?
C1 N3 H4 126.0 . . ?
C2 N3 H4 126.0 . . ?
N1 C1 N3 112.0(2) . . ?
N1 C1 H1 125.7(15) . . ?
N3 C1 H1 122.3(15) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.2(17) . . ?
C6 C5 H5 120.8(17) . . ?
O5 N4 O4 123.9(3) . . ?
O5 N4 C4 117.8(2) . . ?
O4 N4 C4 118.3(2) . . ?
C3 C8 C7 123.0(2) . . ?
C3 C8 N5 118.0(2) . . ?
C7 C8 N5 119.0(2) . . ?
O6 C9 O7 126.7(2) . . ?
O6 C9 C6 115.8(2) . . ?
O7 C9 C6 117.5(2) . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 C9 122.4(2) . . ?
C7 C6 C9 118.3(2) . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 H7 117.7(16) . . ?
C6 C7 H7 123.1(16) . . ?
C3 C4 C5 123.1(2) . . ?
C3 C4 N4 117.1(2) . . ?
C5 C4 N4 119.8(2) . . ?
C8 C3 C4 116.5(2) . . ?
C8 C3 H3 122.2(16) . . ?
C4 C3 H3 121.3(16) . . ?
O2 N5 O3 123.3(2) . . ?
O2 N5 C8 118.5(2) . . ?
O3 N5 C8 118.2(2) . . ?
C9 O7 Co1 125.46(16) . . ?

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
C1 H1 O3 0.92(2) 2.62(2) 3.194(3) 121.4(18) 4_575
O8 H8A O6 0.83(4) 1.76(4) 2.568(3) 162(4) .
O8 H8B O1 0.85(4) 1.98(4) 2.759(3) 153(4) 1_455
N3 H4 O1 0.86 1.93 2.754(3) 159.8 3_775
N2 H2 O7 0.86 2.55 2.978(3) 112.2 .
N2 H2 O8 0.86 2.21 2.843(3) 130.5 1_655
N2 H2 O8 0.86 2.21 2.843(3) 130.5 1_655
N2 H2 O7 0.86 2.55 2.978(3) 112.2 .
N3 H4 O1 0.86 1.93 2.754(3) 159.8 3_775
O8 H8B O1 0.85(4) 1.98(4) 2.759(3) 153(4) 1_455
O8 H8A O6 0.83(4) 1.76(4) 2.568(3) 162(4) .
C1 H1 O3 0.92(2) 2.62(2) 3.194(3) 121.4(18) 4_575

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.89
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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 1407350'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 Cu N6 O8'
_chemical_formula_sum            'C10 H6 Cu N6 O8'
_chemical_formula_weight         401.76

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9317(10)
_cell_length_b                   8.7062(10)
_cell_length_c                   11.2388(15)
_cell_angle_alpha                100.563(2)
_cell_angle_beta                 107.502(2)
_cell_angle_gamma                104.506(2)
_cell_volume                     687.88(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         no
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  'no standards in IP'
_diffrn_standards_decay_%        no
_diffrn_reflns_number            3565
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.45
_reflns_number_total             2556
_reflns_number_gt                1939
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0470P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2507
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.59370(7) 0.13355(6) -0.02451(5) 0.02314(19) Uani 1 1 d . . .
C2 C 1.1319(7) 0.3466(6) 0.5441(5) 0.0410(14) Uani 1 1 d . . .
C0AA C 1.0143(7) 0.3041(6) 0.4159(5) 0.0360(12) Uani 1 1 d . . .
H0AA H 1.0459 0.3606 0.3589 0.043 Uiso 1 1 calc R . .
C4 C 0.8472(7) 0.1740(6) 0.3743(5) 0.0307(12) Uani 1 1 d . . .
C5 C 0.8003(7) 0.0937(6) 0.4615(5) 0.0345(12) Uani 1 1 d . . .
H5 H 0.6877 0.0081 0.4346 0.041 Uiso 1 1 calc R . .
C6 C 0.9222(8) 0.1423(7) 0.5880(5) 0.0415(14) Uani 1 1 d . . .
C7 C 1.0921(8) 0.2678(7) 0.6319(5) 0.0475(16) Uani 1 1 d . . .
H7 H 1.1753 0.2971 0.7172 0.057 Uiso 1 1 calc R . .
C9 C 0.7204(7) 0.1130(6) 0.2323(5) 0.0295(11) Uani 1 1 d . . .
C10 C 0.1633(7) 0.2367(5) 0.0945(5) 0.0330(12) Uani 1 1 d . . .
H10A H 0.0372 0.1763 0.0332 0.040 Uiso 1 1 calc R . .
H10B H 0.1671 0.2236 0.1791 0.040 Uiso 1 1 calc R . .
N11 N 0.1726(6) 0.5115(5) 0.1941(4) 0.0413(12) Uani 1 1 d . . .
C14 C 0.2952(6) 0.1577(6) 0.0550(4) 0.0262(11) Uani 1 1 d . . .
N1 N 0.8774(8) 0.0489(7) 0.6778(5) 0.0508(13) Uani 1 1 d . . .
N2 N 1.3111(7) 0.4841(7) 0.5892(6) 0.0594(15) Uani 1 1 d . . .
C3 C 0.2612(7) 0.5017(6) 0.0305(5) 0.0282(11) Uani 1 1 d . . .
N4 N 0.2705(5) 0.6545(5) 0.0759(4) 0.0286(9) Uani 1 1 d . . .
N5 N 0.2146(6) 0.6569(5) 0.1785(4) 0.0422(12) Uani 1 1 d . . .
N6 N 0.2003(5) 0.4111(4) 0.1013(4) 0.0238(9) Uani 1 1 d . . .
O1 O 0.7519(5) 0.2043(4) 0.1614(3) 0.0352(8) Uani 1 1 d . . .
O2 O 1.4178(7) 0.5110(7) 0.6985(5) 0.0980(19) Uani 1 1 d . . .
O3 O 1.3384(6) 0.5631(6) 0.5155(6) 0.0784(15) Uani 1 1 d . . .
O4 O 1.0015(7) 0.0808(6) 0.7841(4) 0.0748(15) Uani 1 1 d . . .
O5 O 0.7262(8) -0.0554(6) 0.6406(5) 0.0794(15) Uani 1 1 d . . .
O6 O 0.4196(4) 0.2404(4) 0.0223(3) 0.0285(8) Uani 1 1 d . . .
O7 O 0.2634(4) 0.0110(4) 0.0581(3) 0.0314(8) Uani 1 1 d . . .
O8 O 0.5945(4) -0.0232(4) 0.1991(3) 0.0338(8) Uani 1 1 d . . .
H3 H 0.287(7) 0.461(6) -0.034(5) 0.047(17) Uiso 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 O7 1.952(3) 2_655 ?
Cu1 O8 1.957(3) 2_655 ?
Cu1 O1 1.970(3) . ?
Cu1 O6 1.987(3) . ?
Cu1 N4 2.161(4) 2_665 ?
Cu1 Cu1 2.6742(11) 2_655 ?
C2 C7 1.368(8) . ?
C2 C0AA 1.380(7) . ?
C2 N2 1.484(7) . ?
C0AA C4 1.392(7) . ?
C4 C5 1.390(7) . ?
C4 C9 1.515(6) . ?
C5 C6 1.372(7) . ?
C6 C7 1.385(8) . ?
C6 N1 1.476(7) . ?
C9 O8 1.250(5) . ?
C9 O1 1.258(6) . ?
C10 N6 1.456(5) . ?
C10 C14 1.514(6) . ?
N11 N5 1.284(5) . ?
N11 N6 1.342(5) . ?
C14 O7 1.247(5) . ?
C14 O6 1.260(5) . ?
N1 O5 1.205(6) . ?
N1 O4 1.227(6) . ?
N2 O3 1.204(7) . ?
N2 O2 1.204(7) . ?
C3 N4 1.310(6) . ?
C3 N6 1.326(6) . ?
N4 N5 1.352(5) . ?
N4 Cu1 2.161(4) 2_665 ?
O7 Cu1 1.952(3) 2_655 ?
O8 Cu1 1.957(3) 2_655 ?

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
O7 Cu1 O8 89.39(14) 2_655 2_655 ?
O7 Cu1 O1 89.49(14) 2_655 . ?
O8 Cu1 O1 167.45(13) 2_655 . ?
O7 Cu1 O6 167.34(12) 2_655 . ?
O8 Cu1 O6 90.02(13) 2_655 . ?
O1 Cu1 O6 88.33(14) . . ?
O7 Cu1 N4 100.29(14) 2_655 2_665 ?
O8 Cu1 N4 94.88(14) 2_655 2_665 ?
O1 Cu1 N4 97.62(14) . 2_665 ?
O6 Cu1 N4 92.37(14) . 2_665 ?
O7 Cu1 Cu1 80.80(9) 2_655 2_655 ?
O8 Cu1 Cu1 81.48(10) 2_655 2_655 ?
O1 Cu1 Cu1 86.00(10) . 2_655 ?
O6 Cu1 Cu1 86.61(9) . 2_655 ?
N4 Cu1 Cu1 176.21(11) 2_665 2_655 ?
C7 C2 C0AA 123.3(5) . . ?
C7 C2 N2 118.1(5) . . ?
C0AA C2 N2 118.6(6) . . ?
C2 C0AA C4 118.1(5) . . ?
C5 C4 C0AA 120.2(5) . . ?
C5 C4 C9 119.4(4) . . ?
C0AA C4 C9 120.3(5) . . ?
C6 C5 C4 119.1(5) . . ?
C5 C6 C7 122.4(5) . . ?
C5 C6 N1 118.7(5) . . ?
C7 C6 N1 118.7(5) . . ?
C2 C7 C6 116.9(5) . . ?
O8 C9 O1 127.3(5) . . ?
O8 C9 C4 115.8(4) . . ?
O1 C9 C4 117.0(4) . . ?
N6 C10 C14 116.1(4) . . ?
N5 N11 N6 107.4(4) . . ?
O7 C14 O6 127.2(4) . . ?
O7 C14 C10 113.3(4) . . ?
O6 C14 C10 119.6(4) . . ?
O5 N1 O4 125.1(6) . . ?
O5 N1 C6 118.3(5) . . ?
O4 N1 C6 116.6(6) . . ?
O3 N2 O2 124.5(6) . . ?
O3 N2 C2 118.0(6) . . ?
O2 N2 C2 117.5(6) . . ?
N4 C3 N6 109.0(5) . . ?
C3 N4 N5 106.1(4) . . ?
C3 N4 Cu1 126.0(3) . 2_665 ?
N5 N4 Cu1 126.7(3) . 2_665 ?
N11 N5 N4 109.9(4) . . ?
C3 N6 N11 107.6(4) . . ?
C3 N6 C10 132.6(4) . . ?
N11 N6 C10 119.8(4) . . ?
C9 O1 Cu1 119.5(3) . . ?
C14 O6 Cu1 118.2(3) . . ?
C14 O7 Cu1 127.2(3) . 2_655 ?
C9 O8 Cu1 125.7(3) . 2_655 ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.45
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.104
