# 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_n121214d
_database_code_depnum_ccdc_archive 'CCDC 1013117'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 Cu4 N6 O10'
_chemical_formula_weight         674.42

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.843(2)
_cell_length_b                   9.986(2)
_cell_length_c                   12.320(3)
_cell_angle_alpha                67.609(4)
_cell_angle_beta                 78.650(3)
_cell_angle_gamma                68.577(4)
_cell_volume                     828.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2289
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    5.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5123
_exptl_absorpt_correction_T_max  0.5542
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4045
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2881
_reflns_number_gt                2471
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0579P)²+2.9773P] 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         2881
_refine_ls_number_parameters     310
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.058
_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
Cu1 Cu 0.96305(8) 0.68241(8) 0.90984(6) 0.0092(2) Uani 1 1 d U . .
Cu2 Cu 1.55528(9) 0.96142(8) 1.27515(6) 0.0132(2) Uani 1 1 d . . .
Cu3 Cu 1.20240(9) 0.86757(8) 0.96765(6) 0.0111(2) Uani 1 1 d . . .
Cu4 Cu 1.5000 1.0000 1.0000 0.0102(2) Uani 1 2 d S . .
Cu5 Cu 1.0000 0.5000 0.5000 0.0143(3) Uani 1 2 d S . .
O1 O 0.8697(5) 0.6132(5) 0.8137(3) 0.0109(8) Uani 1 1 d . . .
O2 O 0.6895(5) 0.8366(5) 0.6998(4) 0.0154(9) Uani 1 1 d . . .
O3 O 0.8222(5) 0.7044(5) 0.4847(4) 0.0153(9) Uani 1 1 d . . .
O4 O 0.5300(5) 0.8418(5) 0.4425(3) 0.0128(9) Uani 1 1 d . . .
O5 O 0.1403(5) 0.5335(5) 0.5915(4) 0.0145(9) Uani 1 1 d . . .
O6 O 0.1849(5) 0.3244(5) 0.7555(3) 0.0133(9) Uani 1 1 d . . .
O7 O 0.1655(5) 0.4304(5) 0.9522(3) 0.0115(8) Uani 1 1 d . . .
O8 O 0.4377(5) 0.2588(5) 1.0081(4) 0.0172(9) Uani 1 1 d . . .
O9 O 1.6709(5) 0.9739(4) 1.1095(3) 0.0103(8) Uani 1 1 d . . .
H9 H 1.7679 0.8728 1.1174 0.015 Uiso 1 1 calc R . .
O10 O 1.0503(5) 0.7419(5) 1.0141(4) 0.0139(8) Uani 1 1 d U . .
H10' H 1.0879 0.6655 1.0736 0.021 Uiso 1 1 d R . .
N1 N 1.0834(6) 0.8146(5) 0.7801(4) 0.0112(10) Uani 1 1 d . . .
N2 N 1.1890(6) 0.8747(6) 0.8064(4) 0.0121(10) Uani 1 1 d . . .
N3 N 1.2643(6) 0.9541(5) 0.7100(4) 0.0106(10) Uani 1 1 d . . .
N4 N 1.3640(6) 0.8964(5) 1.2443(4) 0.0110(10) Uani 1 1 d . . .
N5 N 1.3424(6) 0.9235(6) 1.1328(4) 0.0117(10) Uani 1 1 d . . .
N6 N 1.2110(6) 0.8717(6) 1.1263(4) 0.0115(10) Uani 1 1 d . . .
C1 C 1.2060(7) 0.9467(7) 0.6176(5) 0.0113(12) Uani 1 1 d . . .
H1 H 1.2372 0.9936 0.5369 0.014 Uiso 1 1 calc R . .
C2 C 1.0929(7) 0.8587(7) 0.6622(5) 0.0142(13) Uani 1 1 d . . .
H2 H 1.0316 0.8331 0.6175 0.017 Uiso 1 1 calc R . .
H3 H 1.0524 0.7644 1.2596 0.017 Uiso 1 1 d R . .
H4 H 1.2216 0.7963 1.3951 0.017 Uiso 1 1 d R . .
C3 C 1.1460(7) 0.8107(7) 1.2372(5) 0.0122(12) Uani 1 1 d . . .
C4 C 1.2399(7) 0.8273(7) 1.3119(5) 0.0125(12) Uani 1 1 d . . .
C5 C 0.6270(7) 0.6090(6) 0.7309(5) 0.0099(12) Uani 1 1 d . . .
C6 C 0.5773(7) 0.6375(7) 0.6192(5) 0.0099(12) Uani 1 1 d . . .
C7 C 0.4470(7) 0.5775(6) 0.6120(5) 0.0085(11) Uani 1 1 d . . .
H7 H 0.4128 0.5963 0.5365 0.010 Uiso 1 1 calc R . .
C8 C 0.3648(7) 0.4915(7) 0.7100(5) 0.0111(12) Uani 1 1 d . . .
C9 C 0.4222(7) 0.4576(6) 0.8219(5) 0.0083(11) Uani 1 1 d . . .
C10 C 0.5549(7) 0.5156(7) 0.8284(5) 0.0104(12) Uani 1 1 d . . .
H10 H 0.5976 0.4897 0.9031 0.013 Uiso 1 1 calc R . .
C11 C 0.7380(7) 0.6953(7) 0.7471(5) 0.0118(13) Uani 1 1 d . . .
C12 C 0.6504(7) 0.7359(7) 0.5076(5) 0.0104(11) Uani 1 1 d U . .
C13 C 0.2187(7) 0.4415(7) 0.6885(5) 0.0126(13) Uani 1 1 d . . .
C14 C 0.3394(7) 0.3720(7) 0.9359(5) 0.0110(12) 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 O10 1.922(4) . ?
Cu1 O1 1.937(4) . ?
Cu1 O7 1.968(4) 2_667 ?
Cu1 N1 1.974(5) . ?
Cu1 O7 2.352(4) 1_655 ?
Cu2 N3 1.959(4) 2_877 ?
Cu2 O4 1.963(4) 1_656 ?
Cu2 N4 1.986(4) . ?
Cu2 O9 2.040(4) . ?
Cu2 O2 2.294(4) 2_777 ?
Cu3 O10 1.898(4) . ?
Cu3 N2 1.983(5) . ?
Cu3 N6 1.986(5) . ?
Cu3 O9 2.008(4) 2_877 ?
Cu4 N5 1.931(5) . ?
Cu4 N5 1.931(5) 2_877 ?
Cu4 O9 1.968(4) 2_877 ?
Cu4 O9 1.968(4) . ?
Cu5 O5 1.908(4) 1_655 ?
Cu5 O5 1.908(4) 2_666 ?
Cu5 O3 1.969(4) 2_766 ?
Cu5 O3 1.969(4) . ?
O1 C11 1.270(7) . ?
O2 C11 1.243(7) . ?
O2 Cu2 2.294(4) 2_777 ?
O3 C12 1.266(7) . ?
O4 C12 1.255(7) . ?
O4 Cu2 1.963(4) 1_454 ?
O5 C13 1.300(7) . ?
O5 Cu5 1.908(4) 1_455 ?
O6 C13 1.235(7) . ?
O7 C14 1.281(6) . ?
O7 Cu1 1.968(4) 2_667 ?
O7 Cu1 2.352(4) 1_455 ?
O8 C14 1.237(7) . ?
O9 Cu3 2.007(4) 2_877 ?
O9 H9 1.0000 . ?
O10 H10' 0.8375 . ?
N1 N2 1.329(6) . ?
N1 C2 1.343(8) . ?
N2 N3 1.318(7) . ?
N3 C1 1.343(7) . ?
N3 Cu2 1.959(4) 2_877 ?
N4 N5 1.327(7) . ?
N4 C4 1.360(7) . ?
N5 N6 1.338(6) . ?
N6 C3 1.347(7) . ?
C1 C2 1.368(8) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.374(8) . ?
C3 H3 0.9486 . ?
C4 H4 0.9495 . ?
C5 C10 1.378(8) . ?
C5 C6 1.400(8) . ?
C5 C11 1.512(7) . ?
C6 C7 1.391(7) . ?
C6 C12 1.502(8) . ?
C7 C8 1.385(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(8) . ?
C8 C13 1.507(7) . ?
C9 C10 1.391(7) . ?
C9 C14 1.502(8) . ?
C10 H10 0.9500 . ?

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
O10 Cu1 O1 176.31(17) . . ?
O10 Cu1 O7 88.02(16) . 2_667 ?
O1 Cu1 O7 88.35(15) . 2_667 ?
O10 Cu1 N1 86.65(17) . . ?
O1 Cu1 N1 97.02(17) . . ?
O7 Cu1 N1 173.15(16) 2_667 . ?
O10 Cu1 O7 98.46(16) . 1_655 ?
O1 Cu1 O7 80.10(15) . 1_655 ?
O7 Cu1 O7 77.93(15) 2_667 1_655 ?
N1 Cu1 O7 107.12(16) . 1_655 ?
N3 Cu2 O4 96.59(18) 2_877 1_656 ?
N3 Cu2 N4 173.6(2) 2_877 . ?
O4 Cu2 N4 89.14(18) 1_656 . ?
N3 Cu2 O9 87.50(16) 2_877 . ?
O4 Cu2 O9 149.96(17) 1_656 . ?
N4 Cu2 O9 88.95(16) . . ?
N3 Cu2 O2 93.21(16) 2_877 2_777 ?
O4 Cu2 O2 90.61(16) 1_656 2_777 ?
N4 Cu2 O2 83.85(16) . 2_777 ?
O9 Cu2 O2 118.96(16) . 2_777 ?
O10 Cu3 N2 84.87(17) . . ?
O10 Cu3 N6 96.71(17) . . ?
N2 Cu3 N6 177.2(2) . . ?
O10 Cu3 O9 168.00(17) . 2_877 ?
N2 Cu3 O9 86.12(17) . 2_877 ?
N6 Cu3 O9 91.99(17) . 2_877 ?
N5 Cu4 N5 179.999(1) . 2_877 ?
N5 Cu4 O9 90.65(17) . 2_877 ?
N5 Cu4 O9 89.35(17) 2_877 2_877 ?
N5 Cu4 O9 89.35(17) . . ?
N5 Cu4 O9 90.65(17) 2_877 . ?
O9 Cu4 O9 180.000(1) 2_877 . ?
O5 Cu5 O5 180.0 1_655 2_666 ?
O5 Cu5 O3 91.37(17) 1_655 2_766 ?
O5 Cu5 O3 88.62(17) 2_666 2_766 ?
O5 Cu5 O3 88.62(17) 1_655 . ?
O5 Cu5 O3 91.38(17) 2_666 . ?
O3 Cu5 O3 179.999(2) 2_766 . ?
C11 O1 Cu1 124.9(4) . . ?
C11 O2 Cu2 135.7(3) . 2_777 ?
C12 O3 Cu5 126.2(4) . . ?
C12 O4 Cu2 129.0(3) . 1_454 ?
C13 O5 Cu5 129.4(4) . 1_455 ?
C14 O7 Cu1 118.5(4) . 2_667 ?
C14 O7 Cu1 133.9(4) . 1_455 ?
Cu1 O7 Cu1 102.07(15) 2_667 1_455 ?
Cu4 O9 Cu3 108.25(19) . 2_877 ?
Cu4 O9 Cu2 113.91(17) . . ?
Cu3 O9 Cu2 115.50(17) 2_877 . ?
Cu4 O9 H9 106.2 . . ?
Cu3 O9 H9 106.2 2_877 . ?
Cu2 O9 H9 106.2 . . ?
Cu3 O10 Cu1 125.3(2) . . ?
Cu3 O10 H10' 110.9 . . ?
Cu1 O10 H10' 109.2 . . ?
N2 N1 C2 106.4(5) . . ?
N2 N1 Cu1 118.7(4) . . ?
C2 N1 Cu1 134.8(4) . . ?
N3 N2 N1 110.7(4) . . ?
N3 N2 Cu3 125.0(3) . . ?
N1 N2 Cu3 123.8(4) . . ?
N2 N3 C1 107.7(4) . . ?
N2 N3 Cu2 118.8(3) . 2_877 ?
C1 N3 Cu2 133.2(4) . 2_877 ?
N5 N4 C4 107.3(4) . . ?
N5 N4 Cu2 117.3(4) . . ?
C4 N4 Cu2 135.3(4) . . ?
N4 N5 N6 110.3(4) . . ?
N4 N5 Cu4 125.1(3) . . ?
N6 N5 Cu4 124.1(4) . . ?
N5 N6 C3 107.4(4) . . ?
N5 N6 Cu3 113.5(3) . . ?
C3 N6 Cu3 137.6(4) . . ?
N3 C1 C2 106.8(5) . . ?
N3 C1 H1 126.6 . . ?
C2 C1 H1 126.6 . . ?
N1 C2 C1 108.3(5) . . ?
N1 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
N6 C3 C4 107.7(5) . . ?
N6 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N4 C4 C3 107.2(5) . . ?
N4 C4 H4 126.4 . . ?
C3 C4 H4 126.4 . . ?
C10 C5 C6 119.3(5) . . ?
C10 C5 C11 119.4(5) . . ?
C6 C5 C11 120.8(5) . . ?
C7 C6 C5 118.1(5) . . ?
C7 C6 C12 118.6(5) . . ?
C5 C6 C12 123.3(5) . . ?
C8 C7 C6 123.0(5) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C9 118.4(5) . . ?
C7 C8 C13 116.9(5) . . ?
C9 C8 C13 124.8(5) . . ?
C10 C9 C8 118.3(5) . . ?
C10 C9 C14 117.3(5) . . ?
C8 C9 C14 124.2(5) . . ?
C5 C10 C9 122.6(5) . . ?
C5 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
O2 C11 O1 126.4(5) . . ?
O2 C11 C5 118.6(5) . . ?
O1 C11 C5 114.9(5) . . ?
O4 C12 O3 125.7(5) . . ?
O4 C12 C6 114.9(5) . . ?
O3 C12 C6 119.3(5) . . ?
O6 C13 O5 125.8(5) . . ?
O6 C13 C8 122.4(5) . . ?
O5 C13 C8 111.8(5) . . ?
O8 C14 O7 124.7(5) . . ?
O8 C14 C9 120.6(5) . . ?
O7 C14 C9 114.6(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
O10 Cu1 O1 C11 115(3) . . . . ?
O7 Cu1 O1 C11 103.9(4) 2_667 . . . ?
N1 Cu1 O1 C11 -71.8(4) . . . . ?
O7 Cu1 O1 C11 -178.0(4) 1_655 . . . ?
O5 Cu5 O3 C12 -128.0(4) 1_655 . . . ?
O5 Cu5 O3 C12 52.0(4) 2_666 . . . ?
O3 Cu5 O3 C12 -102(49) 2_766 . . . ?
N5 Cu4 O9 Cu3 -149.9(2) . . . 2_877 ?
N5 Cu4 O9 Cu3 30.1(2) 2_877 . . 2_877 ?
O9 Cu4 O9 Cu3 -37(100) 2_877 . . 2_877 ?
N5 Cu4 O9 Cu2 -19.9(2) . . . . ?
N5 Cu4 O9 Cu2 160.1(2) 2_877 . . . ?
O9 Cu4 O9 Cu2 93(100) 2_877 . . . ?
N3 Cu2 O9 Cu4 -152.0(2) 2_877 . . . ?
O4 Cu2 O9 Cu4 109.2(3) 1_656 . . . ?
N4 Cu2 O9 Cu4 22.7(2) . . . . ?
O2 Cu2 O9 Cu4 -59.7(2) 2_777 . . . ?
N3 Cu2 O9 Cu3 -25.8(2) 2_877 . . 2_877 ?
O4 Cu2 O9 Cu3 -124.6(3) 1_656 . . 2_877 ?
N4 Cu2 O9 Cu3 148.9(2) . . . 2_877 ?
O2 Cu2 O9 Cu3 66.5(2) 2_777 . . 2_877 ?
N2 Cu3 O10 Cu1 0.4(3) . . . . ?
N6 Cu3 O10 Cu1 178.0(3) . . . . ?
O9 Cu3 O10 Cu1 41.8(9) 2_877 . . . ?
O1 Cu1 O10 Cu3 170(2) . . . . ?
O7 Cu1 O10 Cu3 -179.5(3) 2_667 . . . ?
N1 Cu1 O10 Cu3 -3.9(3) . . . . ?
O7 Cu1 O10 Cu3 103.0(3) 1_655 . . . ?
O10 Cu1 N1 N2 7.8(4) . . . . ?
O1 Cu1 N1 N2 -171.8(4) . . . . ?
O7 Cu1 N1 N2 46.8(17) 2_667 . . . ?
O7 Cu1 N1 N2 -90.0(4) 1_655 . . . ?
O10 Cu1 N1 C2 -175.6(6) . . . . ?
O1 Cu1 N1 C2 4.8(6) . . . . ?
O7 Cu1 N1 C2 -136.6(13) 2_667 . . . ?
O7 Cu1 N1 C2 86.5(6) 1_655 . . . ?
C2 N1 N2 N3 -0.1(6) . . . . ?
Cu1 N1 N2 N3 177.3(3) . . . . ?
C2 N1 N2 Cu3 172.3(4) . . . . ?
Cu1 N1 N2 Cu3 -10.3(6) . . . . ?
O10 Cu3 N2 N3 177.3(5) . . . . ?
N6 Cu3 N2 N3 54(4) . . . . ?
O9 Cu3 N2 N3 5.2(4) 2_877 . . . ?
O10 Cu3 N2 N1 6.0(4) . . . . ?
N6 Cu3 N2 N1 -118(3) . . . . ?
O9 Cu3 N2 N1 -166.1(4) 2_877 . . . ?
N1 N2 N3 C1 0.3(6) . . . . ?
Cu3 N2 N3 C1 -172.0(4) . . . . ?
N1 N2 N3 Cu2 -174.3(3) . . . 2_877 ?
Cu3 N2 N3 Cu2 13.4(6) . . . 2_877 ?
N3 Cu2 N4 N5 38.4(18) 2_877 . . . ?
O4 Cu2 N4 N5 -167.9(4) 1_656 . . . ?
O9 Cu2 N4 N5 -17.9(4) . . . . ?
O2 Cu2 N4 N5 101.4(4) 2_777 . . . ?
N3 Cu2 N4 C4 -141.1(15) 2_877 . . . ?
O4 Cu2 N4 C4 12.6(6) 1_656 . . . ?
O9 Cu2 N4 C4 162.6(6) . . . . ?
O2 Cu2 N4 C4 -78.1(6) 2_777 . . . ?
C4 N4 N5 N6 -1.2(6) . . . . ?
Cu2 N4 N5 N6 179.2(3) . . . . ?
C4 N4 N5 Cu4 -173.0(4) . . . . ?
Cu2 N4 N5 Cu4 7.4(6) . . . . ?
N5 Cu4 N5 N4 114(72) 2_877 . . . ?
O9 Cu4 N5 N4 -171.6(4) 2_877 . . . ?
O9 Cu4 N5 N4 8.4(4) . . . . ?
N5 Cu4 N5 N6 -57(72) 2_877 . . . ?
O9 Cu4 N5 N6 17.6(4) 2_877 . . . ?
O9 Cu4 N5 N6 -162.4(4) . . . . ?
N4 N5 N6 C3 0.5(6) . . . . ?
Cu4 N5 N6 C3 172.4(4) . . . . ?
N4 N5 N6 Cu3 -168.1(3) . . . . ?
Cu4 N5 N6 Cu3 3.8(6) . . . . ?
O10 Cu3 N6 N5 165.7(4) . . . . ?
N2 Cu3 N6 N5 -71(4) . . . . ?
O9 Cu3 N6 N5 -22.6(4) 2_877 . . . ?
O10 Cu3 N6 C3 1.9(6) . . . . ?
N2 Cu3 N6 C3 125(3) . . . . ?
O9 Cu3 N6 C3 173.7(6) 2_877 . . . ?
N2 N3 C1 C2 -0.3(6) . . . . ?
Cu2 N3 C1 C2 173.2(4) 2_877 . . . ?
N2 N1 C2 C1 -0.1(6) . . . . ?
Cu1 N1 C2 C1 -176.9(4) . . . . ?
N3 C1 C2 N1 0.3(6) . . . . ?
N5 N6 C3 C4 0.4(6) . . . . ?
Cu3 N6 C3 C4 164.8(5) . . . . ?
N5 N4 C4 C3 1.4(6) . . . . ?
Cu2 N4 C4 C3 -179.1(4) . . . . ?
N6 C3 C4 N4 -1.1(6) . . . . ?
C10 C5 C6 C7 4.1(8) . . . . ?
C11 C5 C6 C7 -167.9(5) . . . . ?
C10 C5 C6 C12 -179.1(5) . . . . ?
C11 C5 C6 C12 9.0(8) . . . . ?
C5 C6 C7 C8 0.1(8) . . . . ?
C12 C6 C7 C8 -176.9(5) . . . . ?
C6 C7 C8 C9 -2.9(8) . . . . ?
C6 C7 C8 C13 176.8(5) . . . . ?
C7 C8 C9 C10 1.7(8) . . . . ?
C13 C8 C9 C10 -178.0(5) . . . . ?
C7 C8 C9 C14 177.0(5) . . . . ?
C13 C8 C9 C14 -2.7(9) . . . . ?
C6 C5 C10 C9 -5.4(8) . . . . ?
C11 C5 C10 C9 166.6(5) . . . . ?
C8 C9 C10 C5 2.5(8) . . . . ?
C14 C9 C10 C5 -173.2(5) . . . . ?
Cu2 O2 C11 O1 -108.6(6) 2_777 . . . ?
Cu2 O2 C11 C5 68.1(6) 2_777 . . . ?
Cu1 O1 C11 O2 26.9(7) . . . . ?
Cu1 O1 C11 C5 -150.0(3) . . . . ?
C10 C5 C11 O2 -124.1(6) . . . . ?
C6 C5 C11 O2 47.8(7) . . . . ?
C10 C5 C11 O1 53.0(7) . . . . ?
C6 C5 C11 O1 -135.1(5) . . . . ?
Cu2 O4 C12 O3 15.5(8) 1_454 . . . ?
Cu2 O4 C12 C6 -162.1(3) 1_454 . . . ?
Cu5 O3 C12 O4 -132.2(5) . . . . ?
Cu5 O3 C12 C6 45.3(6) . . . . ?
C7 C6 C12 O4 50.3(7) . . . . ?
C5 C6 C12 O4 -126.5(6) . . . . ?
C7 C6 C12 O3 -127.5(5) . . . . ?
C5 C6 C12 O3 55.7(7) . . . . ?
Cu5 O5 C13 O6 -17.1(8) 1_455 . . . ?
Cu5 O5 C13 C8 161.0(3) 1_455 . . . ?
C7 C8 C13 O6 152.3(5) . . . . ?
C9 C8 C13 O6 -28.0(8) . . . . ?
C7 C8 C13 O5 -26.0(7) . . . . ?
C9 C8 C13 O5 153.7(5) . . . . ?
Cu1 O7 C14 O8 -9.5(7) 2_667 . . . ?
Cu1 O7 C14 O8 139.0(5) 1_455 . . . ?
Cu1 O7 C14 C9 173.7(3) 2_667 . . . ?
Cu1 O7 C14 C9 -37.8(6) 1_455 . . . ?
C10 C9 C14 O8 -57.3(7) . . . . ?
C8 C9 C14 O8 127.3(6) . . . . ?
C10 C9 C14 O7 119.6(5) . . . . ?
C8 C9 C14 O7 -55.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.890
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.175
####################################################################### 
# 
# 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_n140430a
_database_code_depnum_ccdc_archive 'CCDC 1013118'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H27 Cu6 N24 O8.50'
_chemical_formula_weight         1168.94

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.6725(9)
_cell_length_b                   8.8145(9)
_cell_length_c                   13.3980(13)
_cell_angle_alpha                78.991(2)
_cell_angle_beta                 73.520(2)
_cell_angle_gamma                82.909(2)
_cell_volume                     961.43(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1853
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.06

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             581
_exptl_absorpt_coefficient_mu    3.341
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_T_max  0.6341
_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5503
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3361
_reflns_number_gt                2642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0340P)²+4.0532P] 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         3361
_refine_ls_number_parameters     307
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.056
_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 0.27201(7) 0.52948(9) 0.24032(5) 0.02008(19) Uani 1 1 d . . .
Cu2 Cu 0.14176(7) 0.36953(8) 0.07062(5) 0.01458(18) Uani 1 1 d . . .
Cu3 Cu 0.5000 0.5000 0.0000 0.0185(2) Uani 1 2 d S . .
Cu4 Cu 0.0000 0.5000 0.5000 0.0399(4) Uani 1 2 d S . .
O1 O 0.3289(4) 0.4080(4) 0.1188(3) 0.0136(8) Uani 1 1 d . . .
H1 H 0.3743 0.3059 0.1451 0.016 Uiso 1 1 calc R . .
N1 N 0.4838(5) 0.6202(6) 0.1891(4) 0.0272(12) Uani 1 1 d . . .
N2 N 0.5673(5) 0.6057(5) 0.0915(3) 0.0169(10) Uani 1 1 d . . .
N3 N 0.7087(5) 0.6657(6) 0.0692(3) 0.0185(10) Uani 1 1 d . . .
N4 N -0.0445(5) 0.4278(6) 0.3780(3) 0.0252(12) Uani 1 1 d . . .
N5 N 0.0613(5) 0.4379(6) 0.2832(3) 0.0209(10) Uani 1 1 d . . .
N6 N 0.0043(5) 0.3764(6) 0.2188(3) 0.0191(10) Uani 1 1 d . . .
N7 N 0.0278(3) 0.7163(4) -0.0386(3) 0.0168(10) Uani 0.737(9) 1 d PG . 1
N8 N 0.1403(5) 0.6142(3) 0.0054(4) 0.0194(12) Uani 0.737(9) 1 d PG . 1
N9 N 0.2747(5) 0.6980(5) -0.0038(5) 0.032(2) Uani 0.737(9) 1 d PG . 1
C9 C 0.2453(5) 0.8520(4) -0.0535(5) 0.024(2) Uani 0.737(9) 1 d PG . 1
H9 H 0.3139 0.9314 -0.0693 0.029 Uiso 0.737(9) 1 calc PR . 1
C10 C 0.0928(5) 0.8633(3) -0.0751(3) 0.0219(13) Uani 0.737(9) 1 d PG . 1
H10 H 0.0440 0.9515 -0.1074 0.026 Uiso 0.737(9) 1 calc PR . 1
N7' N 0.0246(3) 0.7139(4) -0.0389(3) 0.0168(10) Uani 0.263(9) 1 d PG . 2
N8' N 0.1092(5) 0.6227(4) 0.0309(3) 0.0194(12) Uani 0.263(9) 1 d PG . 2
N9' N 0.2097(7) 0.7200(5) 0.0533(4) 0.032(2) Uani 0.263(9) 1 d PG . 2
C9' C 0.1872(7) 0.8714(4) -0.0027(5) 0.024(2) Uani 0.263(9) 1 d PG . 2
H9' H 0.2384 0.9578 -0.0021 0.029 Uiso 0.263(9) 1 calc PR . 2
C10' C 0.0728(5) 0.8676(3) -0.0596(3) 0.0219(13) Uani 0.263(9) 1 d PG . 2
H10' H 0.0359 0.9510 -0.1030 0.026 Uiso 0.263(9) 1 calc PR . 2
N10 N 0.1972(6) 0.8542(6) 0.2703(4) 0.0340(13) Uani 1 1 d . . .
N11 N 0.1751(5) 0.7076(6) 0.3142(3) 0.0226(11) Uani 1 1 d . A .
N12 N 0.0668(5) 0.6984(6) 0.4090(3) 0.0233(11) Uani 1 1 d . A .
O2 O 0.3855(12) 0.3190(12) 0.3144(6) 0.0349(17) Uani 0.496(4) 1 d PD A 1
O3 O 0.2695(9) 0.3746(9) 0.4708(5) 0.0233(13) Uani 0.496(4) 1 d PD A 1
C1 C 0.3559(7) 0.2893(9) 0.4112(6) 0.0189(18) Uani 0.496(4) 1 d PD A 1
C2 C 0.4310(5) 0.1383(5) 0.4577(6) 0.0163(18) Uani 0.496(4) 1 d PDU A 1
C3 C 0.3943(11) 0.0926(7) 0.5661(4) 0.020(3) Uani 0.496(4) 1 d PD . 1
H3 H 0.3233 0.1549 0.6104 0.024 Uiso 0.496(4) 1 calc PR A 1
C4 C 0.5369(11) 0.0456(7) 0.3914(4) 0.022(3) Uani 0.496(4) 1 d PD . 1
H4 H 0.5615 0.0764 0.3186 0.027 Uiso 0.496(4) 1 calc PR A 1
O2' O 0.4351(10) 0.1920(10) 0.2472(6) 0.0349(17) Uani 0.504(4) 1 d PD A 2
O3' O 0.3485(10) 0.3575(9) 0.3559(7) 0.0233(13) Uani 0.504(4) 1 d PD A 2
C1' C 0.4098(7) 0.2298(9) 0.3342(6) 0.0189(18) Uani 0.504(4) 1 d PD A 2
C2' C 0.4572(5) 0.1093(7) 0.4210(5) 0.0163(18) Uani 0.504(4) 1 d PDU A 2
C3' C 0.4148(11) 0.1379(7) 0.5241(4) 0.020(3) Uani 0.504(4) 1 d PD . 2
H3' H 0.3576 0.2304 0.5404 0.024 Uiso 0.504(4) 1 calc PR A 2
C4' C 0.5423(11) -0.0287(7) 0.3973(4) 0.022(3) Uani 0.504(4) 1 d PD . 2
H4' H 0.5708 -0.0481 0.3284 0.027 Uiso 0.504(4) 1 calc PR A 2
C5 C 0.7165(7) 0.7184(9) 0.1543(5) 0.0402(19) Uani 1 1 d . . .
H5 H 0.8027 0.7645 0.1616 0.048 Uiso 1 1 calc R . .
C6 C 0.5727(8) 0.6914(10) 0.2295(5) 0.053(2) Uani 1 1 d . . .
H6 H 0.5431 0.7182 0.2966 0.064 Uiso 1 1 calc R . .
C7 C -0.1429(7) 0.3280(8) 0.2737(4) 0.0288(15) Uani 1 1 d . . .
H7 H -0.2118 0.2817 0.2485 0.035 Uiso 1 1 calc R . .
C8 C -0.1708(7) 0.3604(8) 0.3732(4) 0.0308(15) Uani 1 1 d . . .
H8 H -0.2625 0.3389 0.4284 0.037 Uiso 1 1 calc R . .
C11 C 0.0179(7) 0.8431(8) 0.4249(5) 0.0360(16) Uani 1 1 d . . .
H11 H -0.0575 0.8725 0.4840 0.043 Uiso 1 1 calc R A .
C12 C 0.0986(9) 0.9412(8) 0.3384(6) 0.0429(18) Uani 1 1 d . A .
H12 H 0.0872 1.0489 0.3286 0.051 Uiso 1 1 calc R . .
O4 O 0.3629(12) 0.0839(12) 0.1063(7) 0.0376(17) Uani 0.509(8) 1 d P B 1
O4' O 0.4338(12) -0.0047(12) 0.0901(8) 0.0376(17) Uani 0.491(8) 1 d P B 2
O5 O 0.461(2) 0.532(2) 0.4748(14) 0.041(5) Uani 0.25 1 d P . .


_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 N5 1.978(4) . ?
Cu1 N1 1.980(4) . ?
Cu1 N11 1.987(5) . ?
Cu1 O1 2.030(3) . ?
Cu1 O3' 2.139(9) . ?
Cu1 O2 2.190(9) . ?
Cu2 N7' 1.879(7) 2_565 ?
Cu2 N7 1.917(2) 2_565 ?
Cu2 O1 1.995(3) . ?
Cu2 N3 2.008(4) 2_665 ?
Cu2 N6 2.012(4) . ?
Cu2 N8 2.166(3) . ?
Cu2 N8' 2.195(3) . ?
Cu3 N2 1.920(4) 2_665 ?
Cu3 N2 1.920(4) . ?
Cu3 O1 1.964(3) . ?
Cu3 O1 1.964(3) 2_665 ?
Cu3 N9 2.459(4) 2_665 ?
Cu3 N9 2.459(4) . ?
Cu4 N12 1.979(5) 2_566 ?
Cu4 N12 1.979(5) . ?
Cu4 N4 2.011(4) . ?
Cu4 N4 2.011(4) 2_566 ?
Cu4 O3 2.418(7) 2_566 ?
Cu4 O3 2.418(7) . ?
O1 H1 0.9800 . ?
N1 N2 1.324(6) . ?
N1 C6 1.330(7) . ?
N2 N3 1.329(6) . ?
N3 C5 1.332(7) . ?
N3 Cu2 2.008(4) 2_665 ?
N4 C8 1.331(7) . ?
N4 N5 1.334(6) . ?
N5 N6 1.330(6) . ?
N6 C7 1.355(7) . ?
N7 N8 1.4200 . ?
N7 C10 1.4200 . ?
N7 Cu2 1.917(2) 2_565 ?
N8 N9 1.4200 . ?
N9 C9 1.4200 . ?
C9 C10 1.4200 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N7' N8' 1.4200 . ?
N7' C10' 1.4200 . ?
N7' Cu2 1.879(2) 2_565 ?
N8' N9' 1.4200 . ?
N9' C9' 1.4200 . ?
C9' C10' 1.4200 . ?
C9' H9' 0.9300 . ?
C10' H10' 0.9300 . ?
N10 N11 1.326(7) . ?
N10 C12 1.347(8) . ?
N11 N12 1.343(6) . ?
N12 C11 1.330(8) . ?
O2 C1 1.231(8) . ?
O3 C1 1.231(7) . ?
C1 C2 1.511(8) . ?
C2 C3 1.386(7) . ?
C2 C4 1.389(7) . ?
C3 C4 1.383(6) 2_656 ?
C3 H3 0.9300 . ?
C4 C3 1.383(6) 2_656 ?
C4 H4 0.9300 . ?
O2' C1' 1.226(7) . ?
O3' C1' 1.235(8) . ?
C1' C2' 1.530(8) . ?
C2' C4' 1.384(7) . ?
C2' C3' 1.388(7) . ?
C3' C4' 1.386(6) 2_656 ?
C3' H3' 0.9300 . ?
C4' C3' 1.386(6) 2_656 ?
C4' H4' 0.9300 . ?
C5 C6 1.377(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.365(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 C12 1.373(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O5 O5 1.12(4) 2_666 ?

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
N5 Cu1 N1 176.76(18) . . ?
N5 Cu1 N11 90.96(19) . . ?
N1 Cu1 N11 91.01(19) . . ?
N5 Cu1 O1 86.03(16) . . ?
N1 Cu1 O1 91.11(16) . . ?
N11 Cu1 O1 155.33(17) . . ?
N5 Cu1 O3' 89.0(3) . . ?
N1 Cu1 O3' 93.0(3) . . ?
N11 Cu1 O3' 105.3(2) . . ?
O1 Cu1 O3' 99.1(2) . . ?
N5 Cu1 O2 91.6(3) . . ?
N1 Cu1 O2 89.5(3) . . ?
N11 Cu1 O2 123.3(2) . . ?
O1 Cu1 O2 81.3(2) . . ?
O3' Cu1 O2 18.2(2) . . ?
N7' Cu2 N7 0.23(19) 2_565 2_565 ?
N7' Cu2 O1 166.9(2) 2_565 . ?
N7 Cu2 O1 166.65(14) 2_565 . ?
N7' Cu2 N3 90.2(4) 2_565 2_665 ?
N7 Cu2 N3 90.22(16) 2_565 2_665 ?
O1 Cu2 N3 90.02(15) . 2_665 ?
N7' Cu2 N6 90.4(4) 2_565 . ?
N7 Cu2 N6 90.25(16) 2_565 . ?
O1 Cu2 N6 87.71(15) . . ?
N3 Cu2 N6 172.2(2) 2_665 . ?
N7' Cu2 N8 108.20(15) 2_565 . ?
N7 Cu2 N8 108.42(9) 2_565 . ?
O1 Cu2 N8 84.91(13) . . ?
N3 Cu2 N8 86.56(19) 2_665 . ?
N6 Cu2 N8 100.71(19) . . ?
N7' Cu2 N8' 107.42(17) 2_565 . ?
N7 Cu2 N8' 107.62(10) 2_565 . ?
O1 Cu2 N8' 85.60(14) . . ?
N3 Cu2 N8' 96.62(19) 2_665 . ?
N6 Cu2 N8' 90.70(18) . . ?
N8 Cu2 N8' 10.1 . . ?
N2 Cu3 N2 180.0 2_665 . ?
N2 Cu3 O1 89.13(15) 2_665 . ?
N2 Cu3 O1 90.87(15) . . ?
N2 Cu3 O1 90.87(15) 2_665 2_665 ?
N2 Cu3 O1 89.13(15) . 2_665 ?
O1 Cu3 O1 180.0 . 2_665 ?
N2 Cu3 N9 89.6(5) 2_665 2_665 ?
N2 Cu3 N9 90.4(5) . 2_665 ?
O1 Cu3 N9 101.4(4) . 2_665 ?
O1 Cu3 N9 78.6(4) 2_665 2_665 ?
N2 Cu3 N9 90.44(18) 2_665 . ?
N2 Cu3 N9 89.56(18) . . ?
O1 Cu3 N9 78.57(16) . . ?
O1 Cu3 N9 101.43(16) 2_665 . ?
N9 Cu3 N9 180.0(4) 2_665 . ?
N12 Cu4 N12 179.999(1) 2_566 . ?
N12 Cu4 N4 89.93(19) 2_566 . ?
N12 Cu4 N4 90.07(19) . . ?
N12 Cu4 N4 90.07(19) 2_566 2_566 ?
N12 Cu4 N4 89.93(19) . 2_566 ?
N4 Cu4 N4 179.999(2) . 2_566 ?
N12 Cu4 O3 95.1(2) 2_566 2_566 ?
N12 Cu4 O3 84.9(2) . 2_566 ?
N4 Cu4 O3 86.0(2) . 2_566 ?
N4 Cu4 O3 94.0(2) 2_566 2_566 ?
N12 Cu4 O3 84.9(2) 2_566 . ?
N12 Cu4 O3 95.1(2) . . ?
N4 Cu4 O3 94.0(2) . . ?
N4 Cu4 O3 86.0(2) 2_566 . ?
O3 Cu4 O3 180.0(3) 2_566 . ?
Cu3 O1 Cu2 111.19(16) . . ?
Cu3 O1 Cu1 111.72(16) . . ?
Cu2 O1 Cu1 114.87(16) . . ?
Cu3 O1 H1 106.1 . . ?
Cu2 O1 H1 106.1 . . ?
Cu1 O1 H1 106.1 . . ?
N2 N1 C6 107.5(4) . . ?
N2 N1 Cu1 116.3(3) . . ?
C6 N1 Cu1 136.1(4) . . ?
N1 N2 N3 109.9(4) . . ?
N1 N2 Cu3 124.8(3) . . ?
N3 N2 Cu3 125.1(3) . . ?
N2 N3 C5 107.8(4) . . ?
N2 N3 Cu2 114.1(3) . 2_665 ?
C5 N3 Cu2 137.5(4) . 2_665 ?
C8 N4 N5 107.5(4) . . ?
C8 N4 Cu4 130.2(4) . . ?
N5 N4 Cu4 122.2(3) . . ?
N6 N5 N4 109.7(4) . . ?
N6 N5 Cu1 123.6(3) . . ?
N4 N5 Cu1 126.7(3) . . ?
N5 N6 C7 107.5(4) . . ?
N5 N6 Cu2 118.6(3) . . ?
C7 N6 Cu2 133.9(4) . . ?
N8 N7 C10 108.0 . . ?
N8 N7 Cu2 118.8(2) . 2_565 ?
C10 N7 Cu2 131.03(19) . 2_565 ?
N7 N8 N9 108.0 . . ?
N7 N8 Cu2 132.03(19) . . ?
N9 N8 Cu2 119.89(19) . . ?
C9 N9 N8 108.0 . . ?
C9 N9 Cu3 139.5(2) . . ?
N8 N9 Cu3 105.0(2) . . ?
C10 C9 N9 108.0 . . ?
C10 C9 H9 126.0 . . ?
N9 C9 H9 126.0 . . ?
C9 C10 N7 108.0 . . ?
C9 C10 H10 126.0 . . ?
N7 C10 H10 126.0 . . ?
N8' N7' C10' 108.0 . . ?
N8' N7' Cu2 119.8(2) . 2_565 ?
C10' N7' Cu2 131.5(2) . 2_565 ?
N7' N8' N9' 108.0 . . ?
N7' N8' Cu2 129.3(2) . . ?
N9' N8' Cu2 120.98(19) . . ?
C9' N9' N8' 108.0 . . ?
N9' C9' C10' 108.0 . . ?
N9' C9' H9' 126.0 . . ?
C10' C9' H9' 126.0 . . ?
N7' C10' C9' 108.0 . . ?
N7' C10' H10' 126.0 . . ?
C9' C10' H10' 126.0 . . ?
N11 N10 C12 106.4(5) . . ?
N10 N11 N12 110.9(5) . . ?
N10 N11 Cu1 123.4(4) . . ?
N12 N11 Cu1 125.4(4) . . ?
C11 N12 N11 106.9(5) . . ?
C11 N12 Cu4 129.7(4) . . ?
N11 N12 Cu4 123.5(4) . . ?
C1 O2 Cu1 119.5(6) . . ?
C1 O3 Cu4 137.3(6) . . ?
O3 C1 O2 123.9(8) . . ?
O3 C1 C2 119.2(7) . . ?
O2 C1 C2 117.0(7) . . ?
C3 C2 C4 120.1(4) . . ?
C3 C2 C1 120.1(5) . . ?
C4 C2 C1 119.8(5) . . ?
C4 C3 C2 120.0(4) 2_656 . ?
C4 C3 H3 120.0 2_656 . ?
C2 C3 H3 120.0 . . ?
C3 C4 C2 119.9(4) 2_656 . ?
C3 C4 H4 120.1 2_656 . ?
C2 C4 H4 120.1 . . ?
C1' O3' Cu1 120.7(6) . . ?
O2' C1' O3' 124.3(8) . . ?
O2' C1' C2' 117.2(6) . . ?
O3' C1' C2' 118.5(7) . . ?
C4' C2' C3' 119.7(4) . . ?
C4' C2' C1' 120.3(5) . . ?
C3' C2' C1' 120.0(5) . . ?
C4' C3' C2' 120.0(4) 2_656 . ?
C4' C3' H3' 120.0 2_656 . ?
C2' C3' H3' 120.0 . . ?
C2' C4' C3' 120.3(4) . 2_656 ?
C2' C4' H4' 119.8 . . ?
C3' C4' H4' 119.8 2_656 . ?
N3 C5 C6 107.0(5) . . ?
N3 C5 H5 126.5 . . ?
C6 C5 H5 126.5 . . ?
N1 C6 C5 107.8(5) . . ?
N1 C6 H6 126.1 . . ?
C5 C6 H6 126.1 . . ?
N6 C7 C8 106.8(5) . . ?
N6 C7 H7 126.6 . . ?
C8 C7 H7 126.6 . . ?
N4 C8 C7 108.4(5) . . ?
N4 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
N12 C11 C12 107.8(6) . . ?
N12 C11 H11 126.1 . . ?
C12 C11 H11 126.1 . . ?
N10 C12 C11 108.1(6) . . ?
N10 C12 H12 126.0 . . ?
C11 C12 H12 126.0 . . ?

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
N2 Cu3 O1 Cu2 -29.5(2) 2_665 . . . ?
N2 Cu3 O1 Cu2 150.5(2) . . . . ?
O1 Cu3 O1 Cu2 140(12) 2_665 . . . ?
N9 Cu3 O1 Cu2 -118.8(5) 2_665 . . . ?
N9 Cu3 O1 Cu2 61.17(19) . . . . ?
N2 Cu3 O1 Cu1 -159.2(2) 2_665 . . . ?
N2 Cu3 O1 Cu1 20.8(2) . . . . ?
O1 Cu3 O1 Cu1 10(12) 2_665 . . . ?
N9 Cu3 O1 Cu1 111.4(5) 2_665 . . . ?
N9 Cu3 O1 Cu1 -68.62(19) . . . . ?
N7' Cu2 O1 Cu3 121.6(18) 2_565 . . . ?
N7 Cu2 O1 Cu3 121.9(6) 2_565 . . . ?
N3 Cu2 O1 Cu3 30.8(2) 2_665 . . . ?
N6 Cu2 O1 Cu3 -156.7(2) . . . . ?
N8 Cu2 O1 Cu3 -55.7(2) . . . . ?
N8' Cu2 O1 Cu3 -65.84(19) . . . . ?
N7' Cu2 O1 Cu1 -110.3(18) 2_565 . . . ?
N7 Cu2 O1 Cu1 -110.0(6) 2_565 . . . ?
N3 Cu2 O1 Cu1 158.9(2) 2_665 . . . ?
N6 Cu2 O1 Cu1 -28.6(2) . . . . ?
N8 Cu2 O1 Cu1 72.4(2) . . . . ?
N8' Cu2 O1 Cu1 62.3(2) . . . . ?
N5 Cu1 O1 Cu3 156.8(2) . . . . ?
N1 Cu1 O1 Cu3 -21.7(2) . . . . ?
N11 Cu1 O1 Cu3 73.2(4) . . . . ?
O3' Cu1 O1 Cu3 -114.9(3) . . . . ?
O2 Cu1 O1 Cu3 -111.0(3) . . . . ?
N5 Cu1 O1 Cu2 28.9(2) . . . . ?
N1 Cu1 O1 Cu2 -149.5(2) . . . . ?
N11 Cu1 O1 Cu2 -54.7(4) . . . . ?
O3' Cu1 O1 Cu2 117.3(3) . . . . ?
O2 Cu1 O1 Cu2 121.2(3) . . . . ?
N5 Cu1 N1 N2 -13(4) . . . . ?
N11 Cu1 N1 N2 -140.9(4) . . . . ?
O1 Cu1 N1 N2 14.5(4) . . . . ?
O3' Cu1 N1 N2 113.7(4) . . . . ?
O2 Cu1 N1 N2 95.8(5) . . . . ?
N5 Cu1 N1 C6 170(4) . . . . ?
N11 Cu1 N1 C6 42.0(8) . . . . ?
O1 Cu1 N1 C6 -162.5(8) . . . . ?
O3' Cu1 N1 C6 -63.4(8) . . . . ?
O2 Cu1 N1 C6 -81.2(8) . . . . ?
C6 N1 N2 N3 0.4(7) . . . . ?
Cu1 N1 N2 N3 -177.5(4) . . . . ?
C6 N1 N2 Cu3 176.2(5) . . . . ?
Cu1 N1 N2 Cu3 -1.7(6) . . . . ?
N2 Cu3 N2 N1 129(33) 2_665 . . . ?
O1 Cu3 N2 N1 -12.6(5) . . . . ?
O1 Cu3 N2 N1 167.4(5) 2_665 . . . ?
N9 Cu3 N2 N1 -114.1(6) 2_665 . . . ?
N9 Cu3 N2 N1 65.9(5) . . . . ?
N2 Cu3 N2 N3 -56(33) 2_665 . . . ?
O1 Cu3 N2 N3 162.5(4) . . . . ?
O1 Cu3 N2 N3 -17.5(4) 2_665 . . . ?
N9 Cu3 N2 N3 61.1(6) 2_665 . . . ?
N9 Cu3 N2 N3 -118.9(5) . . . . ?
N1 N2 N3 C5 0.5(7) . . . . ?
Cu3 N2 N3 C5 -175.2(5) . . . . ?
N1 N2 N3 Cu2 173.5(4) . . . 2_665 ?
Cu3 N2 N3 Cu2 -2.3(6) . . . 2_665 ?
N12 Cu4 N4 C8 46.4(6) 2_566 . . . ?
N12 Cu4 N4 C8 -133.6(6) . . . . ?
N4 Cu4 N4 C8 149(75) 2_566 . . . ?
O3 Cu4 N4 C8 -48.7(6) 2_566 . . . ?
O3 Cu4 N4 C8 131.3(6) . . . . ?
N12 Cu4 N4 N5 -131.2(5) 2_566 . . . ?
N12 Cu4 N4 N5 48.8(5) . . . . ?
N4 Cu4 N4 N5 -29(73) 2_566 . . . ?
O3 Cu4 N4 N5 133.7(5) 2_566 . . . ?
O3 Cu4 N4 N5 -46.3(5) . . . . ?
C8 N4 N5 N6 -0.5(7) . . . . ?
Cu4 N4 N5 N6 177.5(4) . . . . ?
C8 N4 N5 Cu1 179.2(4) . . . . ?
Cu4 N4 N5 Cu1 -2.7(7) . . . . ?
N1 Cu1 N5 N6 9(4) . . . . ?
N11 Cu1 N5 N6 136.6(5) . . . . ?
O1 Cu1 N5 N6 -18.9(4) . . . . ?
O3' Cu1 N5 N6 -118.0(5) . . . . ?
O2 Cu1 N5 N6 -100.0(5) . . . . ?
N1 Cu1 N5 N4 -171(4) . . . . ?
N11 Cu1 N5 N4 -43.1(5) . . . . ?
O1 Cu1 N5 N4 161.4(5) . . . . ?
O3' Cu1 N5 N4 62.2(5) . . . . ?
O2 Cu1 N5 N4 80.2(5) . . . . ?
N4 N5 N6 C7 0.9(6) . . . . ?
Cu1 N5 N6 C7 -178.9(4) . . . . ?
N4 N5 N6 Cu2 -178.2(4) . . . . ?
Cu1 N5 N6 Cu2 2.0(6) . . . . ?
N7' Cu2 N6 N5 -176.5(4) 2_565 . . . ?
N7 Cu2 N6 N5 -176.7(4) 2_565 . . . ?
O1 Cu2 N6 N5 16.5(4) . . . . ?
N3 Cu2 N6 N5 89.8(13) 2_665 . . . ?
N8 Cu2 N6 N5 -67.9(4) . . . . ?
N8' Cu2 N6 N5 -69.1(4) . . . . ?
N7' Cu2 N6 C7 4.6(6) 2_565 . . . ?
N7 Cu2 N6 C7 4.4(6) 2_565 . . . ?
O1 Cu2 N6 C7 -162.4(6) . . . . ?
N3 Cu2 N6 C7 -89.1(14) 2_665 . . . ?
N8 Cu2 N6 C7 113.2(6) . . . . ?
N8' Cu2 N6 C7 112.0(6) . . . . ?
C10 N7 N8 N9 0.0 . . . . ?
Cu2 N7 N8 N9 165.0(3) 2_565 . . . ?
C10 N7 N8 Cu2 -176.5(4) . . . . ?
Cu2 N7 N8 Cu2 -11.5(5) 2_565 . . . ?
N7' Cu2 N8 N7 10.7(4) 2_565 . . . ?
N7 Cu2 N8 N7 10.7(4) 2_565 . . . ?
O1 Cu2 N8 N7 -169.9(4) . . . . ?
N3 Cu2 N8 N7 99.7(4) 2_665 . . . ?
N6 Cu2 N8 N7 -83.2(4) . . . . ?
N8' Cu2 N8 N7 -76.5(3) . . . . ?
N7' Cu2 N8 N9 -165.4(6) 2_565 . . . ?
N7 Cu2 N8 N9 -165.5(3) 2_565 . . . ?
O1 Cu2 N8 N9 13.9(3) . . . . ?
N3 Cu2 N8 N9 -76.4(3) 2_665 . . . ?
N6 Cu2 N8 N9 100.6(3) . . . . ?
N8' Cu2 N8 N9 107.38(16) . . . . ?
N7 N8 N9 C9 0.0 . . . . ?
Cu2 N8 N9 C9 177.0(3) . . . . ?
N7 N8 N9 Cu3 -156.2(3) . . . . ?
Cu2 N8 N9 Cu3 20.8(3) . . . . ?
N2 Cu3 N9 C9 -101.4(4) 2_665 . . . ?
N2 Cu3 N9 C9 78.6(4) . . . . ?
O1 Cu3 N9 C9 169.5(4) . . . . ?
O1 Cu3 N9 C9 -10.5(4) 2_665 . . . ?
N9 Cu3 N9 C9 120(100) 2_665 . . . ?
N2 Cu3 N9 N8 42.4(3) 2_665 . . . ?
N2 Cu3 N9 N8 -137.6(3) . . . . ?
O1 Cu3 N9 N8 -46.7(2) . . . . ?
O1 Cu3 N9 N8 133.3(2) 2_665 . . . ?
N9 Cu3 N9 N8 -97(100) 2_665 . . . ?
N8 N9 C9 C10 0.0 . . . . ?
Cu3 N9 C9 C10 143.1(5) . . . . ?
N9 C9 C10 N7 0.0 . . . . ?
N8 N7 C10 C9 0.0 . . . . ?
Cu2 N7 C10 C9 -162.4(4) 2_565 . . . ?
C10' N7' N8' N9' 0.0 . . . . ?
Cu2 N7' N8' N9' -171.3(3) 2_565 . . . ?
C10' N7' N8' Cu2 -164.7(3) . . . . ?
Cu2 N7' N8' Cu2 24.0(4) 2_565 . . . ?
N7' Cu2 N8' N7' -21.7(4) 2_565 . . . ?
N7 Cu2 N8' N7' -21.8(4) 2_565 . . . ?
O1 Cu2 N8' N7' 160.1(3) . . . . ?
N3 Cu2 N8' N7' 70.6(3) 2_665 . . . ?
N6 Cu2 N8' N7' -112.3(3) . . . . ?
N8 Cu2 N8' N7' 74.4(2) . . . . ?
N7' Cu2 N8' N9' 175.4(6) 2_565 . . . ?
N7 Cu2 N8' N9' 175.2(3) 2_565 . . . ?
O1 Cu2 N8' N9' -2.9(3) . . . . ?
N3 Cu2 N8' N9' -92.4(3) 2_665 . . . ?
N6 Cu2 N8' N9' 84.8(3) . . . . ?
N8 Cu2 N8' N9' -88.59(17) . . . . ?
N7' N8' N9' C9' 0.0 . . . . ?
Cu2 N8' N9' C9' 166.2(3) . . . . ?
N8' N9' C9' C10' 0.0 . . . . ?
N8' N7' C10' C9' 0.0 . . . . ?
Cu2 N7' C10' C9' 170.0(4) 2_565 . . . ?
N9' C9' C10' N7' 0.0 . . . . ?
C12 N10 N11 N12 -0.8(7) . . . . ?
C12 N10 N11 Cu1 172.7(4) . . . . ?
N5 Cu1 N11 N10 -131.4(4) . . . . ?
N1 Cu1 N11 N10 46.0(5) . . . . ?
O1 Cu1 N11 N10 -48.9(7) . . . . ?
O3' Cu1 N11 N10 139.4(5) . . . . ?
O2 Cu1 N11 N10 136.0(5) . . . . ?
N5 Cu1 N11 N12 41.1(4) . . . . ?
N1 Cu1 N11 N12 -141.5(4) . . . . ?
O1 Cu1 N11 N12 123.7(4) . . . . ?
O3' Cu1 N11 N12 -48.1(5) . . . . ?
O2 Cu1 N11 N12 -51.4(6) . . . . ?
N10 N11 N12 C11 0.7(6) . . . . ?
Cu1 N11 N12 C11 -172.7(4) . . . . ?
N10 N11 N12 Cu4 179.9(4) . . . . ?
Cu1 N11 N12 Cu4 6.6(6) . . . . ?
N12 Cu4 N12 C11 153(13) 2_566 . . . ?
N4 Cu4 N12 C11 128.1(5) . . . . ?
N4 Cu4 N12 C11 -51.9(5) 2_566 . . . ?
O3 Cu4 N12 C11 42.1(5) 2_566 . . . ?
O3 Cu4 N12 C11 -137.9(5) . . . . ?
N12 Cu4 N12 N11 -27(13) 2_566 . . . ?
N4 Cu4 N12 N11 -51.0(4) . . . . ?
N4 Cu4 N12 N11 129.0(4) 2_566 . . . ?
O3 Cu4 N12 N11 -136.9(4) 2_566 . . . ?
O3 Cu4 N12 N11 43.1(4) . . . . ?
N5 Cu1 O2 C1 -73.5(9) . . . . ?
N1 Cu1 O2 C1 109.6(9) . . . . ?
N11 Cu1 O2 C1 18.7(10) . . . . ?
O1 Cu1 O2 C1 -159.2(9) . . . . ?
O3' Cu1 O2 C1 8.3(9) . . . . ?
N12 Cu4 O3 C1 85.7(9) 2_566 . . . ?
N12 Cu4 O3 C1 -94.3(9) . . . . ?
N4 Cu4 O3 C1 -3.9(10) . . . . ?
N4 Cu4 O3 C1 176.1(10) 2_566 . . . ?
O3 Cu4 O3 C1 116(48) 2_566 . . . ?
Cu4 O3 C1 O2 53.7(14) . . . . ?
Cu4 O3 C1 C2 -126.2(7) . . . . ?
Cu1 O2 C1 O3 -3.0(13) . . . . ?
Cu1 O2 C1 C2 176.9(4) . . . . ?
O3 C1 C2 C3 4.1(8) . . . . ?
O2 C1 C2 C3 -175.7(9) . . . . ?
O3 C1 C2 C4 -175.9(8) . . . . ?
O2 C1 C2 C4 4.3(9) . . . . ?
C4 C2 C3 C4 0.00(4) . . . 2_656 ?
C1 C2 C3 C4 180.00(2) . . . 2_656 ?
C3 C2 C4 C3 0.00(4) . . . 2_656 ?
C1 C2 C4 C3 180.00(2) . . . 2_656 ?
N5 Cu1 O3' C1' 87.0(7) . . . . ?
N1 Cu1 O3' C1' -90.4(7) . . . . ?
N11 Cu1 O3' C1' 177.7(7) . . . . ?
O1 Cu1 O3' C1' 1.2(8) . . . . ?
O2 Cu1 O3' C1' -11.3(10) . . . . ?
Cu1 O3' C1' O2' 1.7(12) . . . . ?
Cu1 O3' C1' C2' -178.0(3) . . . . ?
O2' C1' C2' C4' 7.5(8) . . . . ?
O3' C1' C2' C4' -172.8(8) . . . . ?
O2' C1' C2' C3' -172.5(8) . . . . ?
O3' C1' C2' C3' 7.2(8) . . . . ?
C4' C2' C3' C4' 0.00(4) . . . 2_656 ?
C1' C2' C3' C4' 180.00(2) . . . 2_656 ?
C3' C2' C4' C3' 0.00(4) . . . 2_656 ?
C1' C2' C4' C3' 180.00(2) . . . 2_656 ?
N2 N3 C5 C6 -1.2(8) . . . . ?
Cu2 N3 C5 C6 -171.7(6) 2_665 . . . ?
N2 N1 C6 C5 -1.2(9) . . . . ?
Cu1 N1 C6 C5 176.1(5) . . . . ?
N3 C5 C6 N1 1.5(10) . . . . ?
N5 N6 C7 C8 -0.9(7) . . . . ?
Cu2 N6 C7 C8 178.1(5) . . . . ?
N5 N4 C8 C7 0.0(8) . . . . ?
Cu4 N4 C8 C7 -177.8(5) . . . . ?
N6 C7 C8 N4 0.6(8) . . . . ?
N11 N12 C11 C12 -0.3(7) . . . . ?
Cu4 N12 C11 C12 -179.5(4) . . . . ?
N11 N10 C12 C11 0.6(7) . . . . ?
N12 C11 C12 N10 -0.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.030
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.125
####################################################################### 
# 
# 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_n140321c
_database_code_depnum_ccdc_archive 'CCDC 1013119'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Cu5 N12 O12'
_chemical_formula_weight         988.24

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.5526(10)
_cell_length_b                   10.8749(10)
_cell_length_c                   15.3643(14)
_cell_angle_alpha                76.545(2)
_cell_angle_beta                 82.101(2)
_cell_angle_gamma                79.927(2)
_cell_volume                     1679.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2176
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             982
_exptl_absorpt_coefficient_mu    3.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_T_max  0.7203
_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9408
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5894
_reflns_number_gt                3927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0324P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5894
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Cu1 Cu 0.15906(7) 0.51020(7) 0.15969(4) 0.01948(19) Uani 1 1 d . . .
Cu2 Cu -0.07311(7) 0.76119(7) 0.09159(4) 0.01700(19) Uani 1 1 d . . .
Cu3 Cu 0.0000 0.5000 0.0000 0.0168(2) Uani 1 2 d S . .
Cu4 Cu 0.32016(7) 0.49567(7) 0.34245(4) 0.01753(19) Uani 1 1 d . . .
Cu5 Cu 0.5000 0.5000 0.5000 0.0188(3) Uani 1 2 d S . .
Cu6 Cu 0.61937(7) 0.60361(7) 0.28462(4) 0.01699(19) Uani 1 1 d . . .
O1 O 0.2089(4) 0.3944(4) 0.3045(2) 0.0245(11) Uani 1 1 d . . .
O2 O 0.3138(4) 0.2035(5) 0.3624(3) 0.0390(12) Uani 1 1 d . . .
O3 O -0.2480(4) 0.4572(4) 0.2686(3) 0.0341(11) Uani 1 1 d . . .
O4 O -0.3612(5) 0.3410(5) 0.3813(4) 0.0536(15) Uani 1 1 d . . .
O5 O 0.1630(4) 0.6380(4) -0.0189(3) 0.0299(11) Uani 1 1 d . . .
O6 O 0.0619(4) 0.8285(4) 0.0026(2) 0.0245(10) Uani 1 1 d . . .
O7 O 0.2384(4) 1.2319(4) -0.1711(3) 0.0254(10) Uani 1 1 d . . .
O8 O 0.4236(4) 1.2017(4) -0.2507(2) 0.0240(10) Uani 1 1 d . . .
O9 O -0.0167(3) 0.5421(3) 0.1205(2) 0.0154(9) Uani 1 1 d . . .
H9 H -0.0789 0.4969 0.1642 0.018 Uiso 1 1 calc R . .
O10 O 0.4433(3) 0.5809(3) 0.3819(2) 0.0135(9) Uani 1 1 d . . .
H10' H 0.3996 0.6671 0.3855 0.016 Uiso 1 1 calc R . .
N1 N 0.0305(5) 0.7603(5) 0.1906(3) 0.0213(12) Uani 1 1 d . . .
N2 N 0.1083(5) 0.6541(5) 0.2215(3) 0.0213(12) Uani 1 1 d . . .
N3 N 0.1693(5) 0.6701(5) 0.2887(3) 0.0241(12) Uani 1 1 d . . .
N4 N 0.3486(4) 0.5372(5) 0.1461(3) 0.0193(12) Uani 1 1 d . . .
N5 N 0.4074(4) 0.5331(4) 0.2183(3) 0.0161(11) Uani 1 1 d . . .
N6 N 0.5170(5) 0.5794(5) 0.1928(3) 0.0205(12) Uani 1 1 d . . .
N7 N 0.2013(5) 0.3533(5) 0.1076(3) 0.0197(12) Uani 1 1 d . . .
N8 N 0.1336(4) 0.3574(4) 0.0396(3) 0.0179(12) Uani 1 1 d . . .
N9 N 0.1691(5) 0.2505(5) 0.0103(3) 0.0196(12) Uani 1 1 d . . .
N10 N 0.7114(4) 0.6166(5) 0.3864(3) 0.0200(12) Uani 1 1 d . . .
N11 N 0.6604(4) 0.5718(4) 0.4684(3) 0.0164(12) Uani 1 1 d . . .
N12 N 0.7427(5) 0.5675(5) 0.5285(3) 0.0215(13) Uani 1 1 d . . .
C1 C 0.1256(6) 0.7897(6) 0.2989(4) 0.0289(16) Uani 1 1 d . . .
H1 H 0.1503 0.8276 0.3410 0.035 Uiso 1 1 calc R . .
C2 C 0.0394(6) 0.8473(6) 0.2380(4) 0.0302(16) Uani 1 1 d . . .
H2 H -0.0046 0.9303 0.2307 0.036 Uiso 1 1 calc R . .
C3 C 0.5308(6) 0.6127(6) 0.1029(4) 0.0297(17) Uani 1 1 d . . .
H3 H 0.5998 0.6471 0.0669 0.036 Uiso 1 1 calc R . .
C4 C 0.4226(6) 0.5861(6) 0.0743(4) 0.0244(16) Uani 1 1 d . . .
H4 H 0.4048 0.6000 0.0149 0.029 Uiso 1 1 calc R . .
C5 C 0.2611(6) 0.1767(6) 0.0598(4) 0.0277(16) Uani 1 1 d . . .
H5 H 0.3034 0.0962 0.0535 0.033 Uiso 1 1 calc R . .
C6 C 0.2803(6) 0.2429(6) 0.1206(4) 0.0310(17) Uani 1 1 d . . .
H6 H 0.3386 0.2156 0.1639 0.037 Uiso 1 1 calc R . .
C7 C 0.8468(6) 0.6132(7) 0.4833(4) 0.0317(18) Uani 1 1 d . . .
H7 H 0.9195 0.6230 0.5076 0.038 Uiso 1 1 calc R . .
C8 C 0.8272(6) 0.6431(7) 0.3939(4) 0.0324(18) Uani 1 1 d . . .
H8 H 0.8850 0.6764 0.3465 0.039 Uiso 1 1 calc R . .
C9 C 0.0916(6) 0.2206(6) 0.3456(3) 0.0189(14) Uani 1 1 d . . .
C10 C -0.0214(6) 0.3032(6) 0.3291(4) 0.0264(16) Uani 1 1 d . . .
H10 H -0.0177 0.3900 0.3080 0.032 Uiso 1 1 calc R . .
C11 C -0.1405(6) 0.2609(6) 0.3429(4) 0.0271(16) Uani 1 1 d . . .
C12 C -0.1450(6) 0.1308(6) 0.3751(4) 0.0309(17) Uani 1 1 d . . .
H12 H -0.2242 0.1006 0.3868 0.037 Uiso 1 1 calc R . .
C13 C -0.0326(6) 0.0470(6) 0.3896(4) 0.0319(17) Uani 1 1 d . . .
H13 H -0.0356 -0.0401 0.4089 0.038 Uiso 1 1 calc R . .
C14 C 0.0848(6) 0.0918(6) 0.3754(4) 0.0274(15) Uani 1 1 d . . .
H14 H 0.1603 0.0344 0.3861 0.033 Uiso 1 1 calc R . .
C15 C 0.2168(6) 0.2712(7) 0.3376(4) 0.0216(15) Uani 1 1 d . . .
C16 C -0.2616(7) 0.3588(7) 0.3304(5) 0.0337(18) Uani 1 1 d . . .
C17 C 0.2423(5) 0.8245(5) -0.1071(3) 0.0162(13) Uani 1 1 d . . .
C18 C 0.2410(5) 0.9560(5) -0.1190(3) 0.0165(13) Uani 1 1 d . . .
H18 H 0.1825 1.0032 -0.0837 0.020 Uiso 1 1 calc R . .
C19 C 0.3292(6) 1.0158(6) -0.1851(3) 0.0193(14) Uani 1 1 d . . .
C20 C 0.4141(6) 0.9456(6) -0.2371(4) 0.0236(15) Uani 1 1 d . . .
H20 H 0.4724 0.9858 -0.2808 0.028 Uiso 1 1 calc R . .
C21 C 0.4144(6) 0.8159(6) -0.2256(4) 0.0262(15) Uani 1 1 d . . .
H21 H 0.4718 0.7691 -0.2617 0.031 Uiso 1 1 calc R . .
C22 C 0.3287(6) 0.7562(6) -0.1598(4) 0.0226(15) Uani 1 1 d . . .
H22 H 0.3296 0.6685 -0.1512 0.027 Uiso 1 1 calc R . .
C23 C 0.1501(6) 0.7568(6) -0.0362(4) 0.0222(15) Uani 1 1 d . . .
C24 C 0.3297(6) 1.1586(6) -0.2022(3) 0.0169(14) Uani 1 1 d . . .
O11 O 0.4062(12) 0.1021(11) 0.5366(7) 0.078(3) Uani 0.531(7) 1 d P A 1
O11' O 0.5140(13) 0.1499(13) 0.4702(8) 0.078(3) Uani 0.469(7) 1 d P A 2
O12' O 0.6332(19) 0.1655(19) 0.6131(12) 0.049(3) Uani 0.458(15) 1 d P B 1
O12 O 0.6401(15) 0.1905(15) 0.5629(10) 0.049(3) Uani 0.542(15) 1 d P B 2


_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 1.974(5) . ?
Cu1 O9 1.977(3) . ?
Cu1 N7 2.006(5) . ?
Cu1 N4 2.047(4) . ?
Cu1 O1 2.366(4) . ?
Cu2 O6 1.949(4) . ?
Cu2 O7 1.988(4) 2_575 ?
Cu2 N1 1.989(4) . ?
Cu2 N9 2.017(4) 2_565 ?
Cu2 O9 2.304(4) . ?
Cu3 N8 1.947(5) . ?
Cu3 N8 1.947(5) 2_565 ?
Cu3 O9 1.987(3) 2_565 ?
Cu3 O9 1.987(3) . ?
Cu3 O5 2.420(3) . ?
Cu3 O5 2.420(3) 2_565 ?
Cu4 O10 1.953(3) . ?
Cu4 O1 1.968(3) . ?
Cu4 N5 1.984(4) . ?
Cu4 N12 2.002(4) 2_666 ?
Cu4 N3 2.322(5) . ?
Cu5 N11 1.942(4) . ?
Cu5 N11 1.942(4) 2_666 ?
Cu5 O10 1.949(3) 2_666 ?
Cu5 O10 1.949(3) . ?
Cu6 O3 1.965(5) 1_655 ?
Cu6 N6 1.980(4) . ?
Cu6 N10 1.994(4) . ?
Cu6 O8 2.044(4) 2_675 ?
Cu6 O10 2.230(3) . ?
O1 C15 1.310(7) . ?
O2 C15 1.203(7) . ?
O3 C16 1.269(7) . ?
O3 Cu6 1.965(5) 1_455 ?
O4 C16 1.237(8) . ?
O5 C23 1.244(7) . ?
O6 C23 1.281(8) . ?
O7 C24 1.255(7) . ?
O7 Cu2 1.988(4) 2_575 ?
O8 C24 1.246(6) . ?
O8 Cu6 2.044(4) 2_675 ?
O9 H9 0.9800 . ?
O10 H10' 0.9800 . ?
N1 N2 1.324(7) . ?
N1 C2 1.343(7) . ?
N2 N3 1.347(5) . ?
N3 C1 1.339(8) . ?
N4 C4 1.322(6) . ?
N4 N5 1.332(5) . ?
N5 N6 1.316(5) . ?
N6 C3 1.337(6) . ?
N7 C6 1.327(8) . ?
N7 N8 1.333(5) . ?
N8 N9 1.319(6) . ?
N9 C5 1.346(7) . ?
N9 Cu2 2.017(4) 2_565 ?
N10 N11 1.317(5) . ?
N10 C8 1.329(7) . ?
N11 N12 1.340(5) . ?
N12 C7 1.326(6) . ?
N12 Cu4 2.002(4) 2_666 ?
C1 C2 1.363(8) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.361(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.372(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.377(8) . ?
C9 C14 1.380(8) . ?
C9 C15 1.497(7) . ?
C10 C11 1.385(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(8) . ?
C11 C16 1.516(9) . ?
C12 C13 1.373(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C17 C22 1.371(8) . ?
C17 C18 1.397(7) . ?
C17 C23 1.503(7) . ?
C18 C19 1.402(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C19 C24 1.514(8) . ?
C20 C21 1.380(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(7) . ?
C21 H21 0.9300 . ?
C22 H22 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 O9 88.75(17) . . ?
N2 Cu1 N7 174.24(18) . . ?
O9 Cu1 N7 90.22(16) . . ?
N2 Cu1 N4 90.35(19) . . ?
O9 Cu1 N4 153.64(16) . . ?
N7 Cu1 N4 93.08(19) . . ?
N2 Cu1 O1 83.14(17) . . ?
O9 Cu1 O1 123.26(13) . . ?
N7 Cu1 O1 92.70(16) . . ?
N4 Cu1 O1 82.72(15) . . ?
O6 Cu2 O7 156.53(18) . 2_575 ?
O6 Cu2 N1 90.52(17) . . ?
O7 Cu2 N1 92.76(17) 2_575 . ?
O6 Cu2 N9 88.56(16) . 2_565 ?
O7 Cu2 N9 89.82(17) 2_575 2_565 ?
N1 Cu2 N9 175.5(2) . 2_565 ?
O6 Cu2 O9 105.66(16) . . ?
O7 Cu2 O9 97.72(15) 2_575 . ?
N1 Cu2 O9 86.98(17) . . ?
N9 Cu2 O9 89.04(16) 2_565 . ?
N8 Cu3 N8 179.999(2) . 2_565 ?
N8 Cu3 O9 91.01(16) . 2_565 ?
N8 Cu3 O9 88.99(16) 2_565 2_565 ?
N8 Cu3 O9 88.99(16) . . ?
N8 Cu3 O9 91.01(16) 2_565 . ?
O9 Cu3 O9 180.0 2_565 . ?
N8 Cu3 O5 87.22(15) . . ?
N8 Cu3 O5 92.79(15) 2_565 . ?
O9 Cu3 O5 101.97(13) 2_565 . ?
O9 Cu3 O5 78.03(13) . . ?
N8 Cu3 O5 92.79(15) . 2_565 ?
N8 Cu3 O5 87.21(15) 2_565 2_565 ?
O9 Cu3 O5 78.03(13) 2_565 2_565 ?
O9 Cu3 O5 101.97(13) . 2_565 ?
O5 Cu3 O5 180.0 . 2_565 ?
O10 Cu4 O1 174.33(18) . . ?
O10 Cu4 N5 89.39(14) . . ?
O1 Cu4 N5 90.15(15) . . ?
O10 Cu4 N12 88.99(14) . 2_666 ?
O1 Cu4 N12 90.49(15) . 2_666 ?
N5 Cu4 N12 170.0(2) . 2_666 ?
O10 Cu4 N3 100.52(16) . . ?
O1 Cu4 N3 85.05(16) . . ?
N5 Cu4 N3 84.18(18) . . ?
N12 Cu4 N3 105.79(19) 2_666 . ?
N11 Cu5 N11 179.999(1) . 2_666 ?
N11 Cu5 O10 88.84(15) . 2_666 ?
N11 Cu5 O10 91.16(15) 2_666 2_666 ?
N11 Cu5 O10 91.16(15) . . ?
N11 Cu5 O10 88.84(15) 2_666 . ?
O10 Cu5 O10 180.000(1) 2_666 . ?
O3 Cu6 N6 93.03(19) 1_655 . ?
O3 Cu6 N10 87.16(19) 1_655 . ?
N6 Cu6 N10 174.14(18) . . ?
O3 Cu6 O8 143.91(17) 1_655 2_675 ?
N6 Cu6 O8 92.98(18) . 2_675 ?
N10 Cu6 O8 90.29(17) . 2_675 ?
O3 Cu6 O10 121.80(16) 1_655 . ?
N6 Cu6 O10 87.09(15) . . ?
N10 Cu6 O10 87.83(15) . . ?
O8 Cu6 O10 94.03(15) 2_675 . ?
C15 O1 Cu4 120.3(3) . . ?
C15 O1 Cu1 128.8(3) . . ?
Cu4 O1 Cu1 104.56(15) . . ?
C16 O3 Cu6 112.2(5) . 1_455 ?
C23 O5 Cu3 129.1(4) . . ?
C23 O6 Cu2 122.8(4) . . ?
C24 O7 Cu2 144.4(4) . 2_575 ?
C24 O8 Cu6 108.6(4) . 2_675 ?
Cu1 O9 Cu3 107.16(18) . . ?
Cu1 O9 Cu2 105.05(13) . . ?
Cu3 O9 Cu2 103.78(14) . . ?
Cu1 O9 H9 113.3 . . ?
Cu3 O9 H9 113.3 . . ?
Cu2 O9 H9 113.3 . . ?
Cu5 O10 Cu4 114.85(16) . . ?
Cu5 O10 Cu6 107.77(15) . . ?
Cu4 O10 Cu6 112.91(15) . . ?
Cu5 O10 H10' 107.0 . . ?
Cu4 O10 H10' 107.0 . . ?
Cu6 O10 H10' 107.0 . . ?
N2 N1 C2 108.2(4) . . ?
N2 N1 Cu2 118.1(3) . . ?
C2 N1 Cu2 133.6(5) . . ?
N1 N2 N3 110.1(5) . . ?
N1 N2 Cu1 124.3(3) . . ?
N3 N2 Cu1 124.1(4) . . ?
C1 N3 N2 105.8(5) . . ?
C1 N3 Cu4 140.3(4) . . ?
N2 N3 Cu4 113.7(4) . . ?
C4 N4 N5 107.8(4) . . ?
C4 N4 Cu1 130.3(4) . . ?
N5 N4 Cu1 120.3(3) . . ?
N6 N5 N4 109.4(4) . . ?
N6 N5 Cu4 126.9(3) . . ?
N4 N5 Cu4 122.6(3) . . ?
N5 N6 C3 108.4(4) . . ?
N5 N6 Cu6 119.5(3) . . ?
C3 N6 Cu6 131.7(4) . . ?
C6 N7 N8 108.1(5) . . ?
C6 N7 Cu1 138.1(4) . . ?
N8 N7 Cu1 113.8(4) . . ?
N9 N8 N7 108.8(5) . . ?
N9 N8 Cu3 128.9(3) . . ?
N7 N8 Cu3 122.3(4) . . ?
N8 N9 C5 108.5(4) . . ?
N8 N9 Cu2 114.2(4) . 2_565 ?
C5 N9 Cu2 137.3(4) . 2_565 ?
N11 N10 C8 106.9(4) . . ?
N11 N10 Cu6 117.2(3) . . ?
C8 N10 Cu6 135.0(4) . . ?
N10 N11 N12 110.3(4) . . ?
N10 N11 Cu5 126.2(3) . . ?
N12 N11 Cu5 123.0(3) . . ?
C7 N12 N11 107.2(4) . . ?
C7 N12 Cu4 136.8(3) . 2_666 ?
N11 N12 Cu4 115.9(3) . 2_666 ?
N3 C1 C2 109.5(5) . . ?
N3 C1 H1 125.3 . . ?
C2 C1 H1 125.3 . . ?
N1 C2 C1 106.4(6) . . ?
N1 C2 H2 126.8 . . ?
C1 C2 H2 126.8 . . ?
N6 C3 C4 106.4(5) . . ?
N6 C3 H3 126.8 . . ?
C4 C3 H3 126.8 . . ?
N4 C4 C3 108.0(5) . . ?
N4 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
N9 C5 C6 106.5(6) . . ?
N9 C5 H5 126.7 . . ?
C6 C5 H5 126.7 . . ?
N7 C6 C5 108.1(5) . . ?
N7 C6 H6 126.0 . . ?
C5 C6 H6 126.0 . . ?
N12 C7 C8 107.1(5) . . ?
N12 C7 H7 126.4 . . ?
C8 C7 H7 126.4 . . ?
N10 C8 C7 108.4(5) . . ?
N10 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
C10 C9 C14 118.3(5) . . ?
C10 C9 C15 120.3(5) . . ?
C14 C9 C15 121.2(6) . . ?
C9 C10 C11 122.0(6) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 C16 118.8(6) . . ?
C12 C11 C16 122.4(6) . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.9(6) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O2 C15 O1 124.2(5) . . ?
O2 C15 C9 121.8(6) . . ?
O1 C15 C9 114.0(6) . . ?
O4 C16 O3 125.5(7) . . ?
O4 C16 C11 119.6(6) . . ?
O3 C16 C11 114.8(6) . . ?
C22 C17 C18 119.9(5) . . ?
C22 C17 C23 119.6(5) . . ?
C18 C17 C23 120.5(5) . . ?
C17 C18 C19 118.9(6) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.0(5) . . ?
C20 C19 C24 119.0(5) . . ?
C18 C19 C24 121.0(5) . . ?
C19 C20 C21 120.9(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C22 119.4(6) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C21 120.9(5) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
O5 C23 O6 124.4(5) . . ?
O5 C23 C17 119.6(6) . . ?
O6 C23 C17 116.0(5) . . ?
O8 C24 O7 120.8(5) . . ?
O8 C24 C19 117.2(5) . . ?
O7 C24 C19 121.9(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
O10 Cu4 O1 C15 30.0(16) . . . . ?
N5 Cu4 O1 C15 115.3(4) . . . . ?
N12 Cu4 O1 C15 -54.7(5) 2_666 . . . ?
N3 Cu4 O1 C15 -160.5(4) . . . . ?
O10 Cu4 O1 Cu1 -124.4(14) . . . . ?
N5 Cu4 O1 Cu1 -39.1(2) . . . . ?
N12 Cu4 O1 Cu1 150.9(2) 2_666 . . . ?
N3 Cu4 O1 Cu1 45.06(18) . . . . ?
N2 Cu1 O1 C15 156.9(5) . . . . ?
O9 Cu1 O1 C15 73.0(5) . . . . ?
N7 Cu1 O1 C15 -19.1(5) . . . . ?
N4 Cu1 O1 C15 -111.8(5) . . . . ?
N2 Cu1 O1 Cu4 -51.6(2) . . . . ?
O9 Cu1 O1 Cu4 -135.60(17) . . . . ?
N7 Cu1 O1 Cu4 132.4(2) . . . . ?
N4 Cu1 O1 Cu4 39.6(2) . . . . ?
N8 Cu3 O5 C23 -171.9(5) . . . . ?
N8 Cu3 O5 C23 8.1(5) 2_565 . . . ?
O9 Cu3 O5 C23 97.6(5) 2_565 . . . ?
O9 Cu3 O5 C23 -82.3(5) . . . . ?
O5 Cu3 O5 C23 26(3) 2_565 . . . ?
O7 Cu2 O6 C23 -166.7(4) 2_575 . . . ?
N1 Cu2 O6 C23 95.1(5) . . . . ?
N9 Cu2 O6 C23 -80.5(5) 2_565 . . . ?
O9 Cu2 O6 C23 8.1(5) . . . . ?
N2 Cu1 O9 Cu3 146.40(18) . . . . ?
N7 Cu1 O9 Cu3 -39.27(18) . . . . ?
N4 Cu1 O9 Cu3 58.1(4) . . . . ?
O1 Cu1 O9 Cu3 -132.65(16) . . . . ?
N2 Cu1 O9 Cu2 36.46(17) . . . . ?
N7 Cu1 O9 Cu2 -149.21(17) . . . . ?
N4 Cu1 O9 Cu2 -51.8(4) . . . . ?
O1 Cu1 O9 Cu2 117.41(15) . . . . ?
N8 Cu3 O9 Cu1 37.55(18) . . . . ?
N8 Cu3 O9 Cu1 -142.45(18) 2_565 . . . ?
O9 Cu3 O9 Cu1 -107(4) 2_565 . . . ?
O5 Cu3 O9 Cu1 -49.82(16) . . . . ?
O5 Cu3 O9 Cu1 130.19(16) 2_565 . . . ?
N8 Cu3 O9 Cu2 148.38(16) . . . . ?
N8 Cu3 O9 Cu2 -31.62(16) 2_565 . . . ?
O9 Cu3 O9 Cu2 4(4) 2_565 . . . ?
O5 Cu3 O9 Cu2 61.01(15) . . . . ?
O5 Cu3 O9 Cu2 -118.99(15) 2_565 . . . ?
O6 Cu2 O9 Cu1 56.63(18) . . . . ?
O7 Cu2 O9 Cu1 -125.44(16) 2_575 . . . ?
N1 Cu2 O9 Cu1 -33.06(18) . . . . ?
N9 Cu2 O9 Cu1 144.87(18) 2_565 . . . ?
O6 Cu2 O9 Cu3 -55.73(17) . . . . ?
O7 Cu2 O9 Cu3 122.19(16) 2_575 . . . ?
N1 Cu2 O9 Cu3 -145.43(18) . . . . ?
N9 Cu2 O9 Cu3 32.50(18) 2_565 . . . ?
N11 Cu5 O10 Cu4 154.6(2) . . . . ?
N11 Cu5 O10 Cu4 -25.4(2) 2_666 . . . ?
O10 Cu5 O10 Cu4 -122(67) 2_666 . . . ?
N11 Cu5 O10 Cu6 27.82(19) . . . . ?
N11 Cu5 O10 Cu6 -152.18(19) 2_666 . . . ?
O10 Cu5 O10 Cu6 111(67) 2_666 . . . ?
O1 Cu4 O10 Cu5 -56.2(15) . . . . ?
N5 Cu4 O10 Cu5 -141.6(2) . . . . ?
N12 Cu4 O10 Cu5 28.6(2) 2_666 . . . ?
N3 Cu4 O10 Cu5 134.4(2) . . . . ?
O1 Cu4 O10 Cu6 67.9(14) . . . . ?
N5 Cu4 O10 Cu6 -17.5(2) . . . . ?
N12 Cu4 O10 Cu6 152.7(2) 2_666 . . . ?
N3 Cu4 O10 Cu6 -101.46(19) . . . . ?
O3 Cu6 O10 Cu5 56.0(2) 1_655 . . . ?
N6 Cu6 O10 Cu5 147.8(2) . . . . ?
N10 Cu6 O10 Cu5 -29.3(2) . . . . ?
O8 Cu6 O10 Cu5 -119.43(17) 2_675 . . . ?
O3 Cu6 O10 Cu4 -71.9(2) 1_655 . . . ?
N6 Cu6 O10 Cu4 19.9(2) . . . . ?
N10 Cu6 O10 Cu4 -157.2(2) . . . . ?
O8 Cu6 O10 Cu4 112.65(19) 2_675 . . . ?
O6 Cu2 N1 N2 -92.7(4) . . . . ?
O7 Cu2 N1 N2 110.5(4) 2_575 . . . ?
N9 Cu2 N1 N2 -15(2) 2_565 . . . ?
O9 Cu2 N1 N2 12.9(4) . . . . ?
O6 Cu2 N1 C2 88.7(5) . . . . ?
O7 Cu2 N1 C2 -68.0(5) 2_575 . . . ?
N9 Cu2 N1 C2 167(2) 2_565 . . . ?
O9 Cu2 N1 C2 -165.6(5) . . . . ?
C2 N1 N2 N3 -0.3(6) . . . . ?
Cu2 N1 N2 N3 -179.2(3) . . . . ?
C2 N1 N2 Cu1 -166.7(4) . . . . ?
Cu2 N1 N2 Cu1 14.4(5) . . . . ?
O9 Cu1 N2 N1 -36.3(4) . . . . ?
N7 Cu1 N2 N1 -116.0(18) . . . . ?
N4 Cu1 N2 N1 117.3(4) . . . . ?
O1 Cu1 N2 N1 -160.0(4) . . . . ?
O9 Cu1 N2 N3 159.2(4) . . . . ?
N7 Cu1 N2 N3 79(2) . . . . ?
N4 Cu1 N2 N3 -47.2(4) . . . . ?
O1 Cu1 N2 N3 35.5(4) . . . . ?
N1 N2 N3 C1 0.5(6) . . . . ?
Cu1 N2 N3 C1 167.0(4) . . . . ?
N1 N2 N3 Cu4 -175.9(3) . . . . ?
Cu1 N2 N3 Cu4 -9.4(5) . . . . ?
O10 Cu4 N3 C1 -24.2(7) . . . . ?
O1 Cu4 N3 C1 156.8(6) . . . . ?
N5 Cu4 N3 C1 -112.5(6) . . . . ?
N12 Cu4 N3 C1 67.7(7) 2_666 . . . ?
O10 Cu4 N3 N2 150.4(3) . . . . ?
O1 Cu4 N3 N2 -28.6(3) . . . . ?
N5 Cu4 N3 N2 62.1(4) . . . . ?
N12 Cu4 N3 N2 -117.7(4) 2_666 . . . ?
N2 Cu1 N4 C4 -106.4(5) . . . . ?
O9 Cu1 N4 C4 -18.5(8) . . . . ?
N7 Cu1 N4 C4 78.3(5) . . . . ?
O1 Cu1 N4 C4 170.6(5) . . . . ?
N2 Cu1 N4 N5 57.2(4) . . . . ?
O9 Cu1 N4 N5 145.1(4) . . . . ?
N7 Cu1 N4 N5 -118.1(4) . . . . ?
O1 Cu1 N4 N5 -25.8(4) . . . . ?
C4 N4 N5 N6 0.3(7) . . . . ?
Cu1 N4 N5 N6 -166.6(4) . . . . ?
C4 N4 N5 Cu4 169.0(4) . . . . ?
Cu1 N4 N5 Cu4 2.1(6) . . . . ?
O10 Cu4 N5 N6 9.1(5) . . . . ?
O1 Cu4 N5 N6 -165.3(5) . . . . ?
N12 Cu4 N5 N6 -71.6(11) 2_666 . . . ?
N3 Cu4 N5 N6 109.7(5) . . . . ?
O10 Cu4 N5 N4 -157.5(5) . . . . ?
O1 Cu4 N5 N4 28.1(5) . . . . ?
N12 Cu4 N5 N4 121.8(9) 2_666 . . . ?
N3 Cu4 N5 N4 -56.9(4) . . . . ?
N4 N5 N6 C3 -0.7(7) . . . . ?
Cu4 N5 N6 C3 -168.8(4) . . . . ?
N4 N5 N6 Cu6 173.6(4) . . . . ?
Cu4 N5 N6 Cu6 5.6(6) . . . . ?
O3 Cu6 N6 N5 106.8(4) 1_655 . . . ?
N10 Cu6 N6 N5 15(2) . . . . ?
O8 Cu6 N6 N5 -108.8(4) 2_675 . . . ?
O10 Cu6 N6 N5 -14.9(4) . . . . ?
O3 Cu6 N6 C3 -80.4(6) 1_655 . . . ?
N10 Cu6 N6 C3 -172.1(19) . . . . ?
O8 Cu6 N6 C3 64.0(6) 2_675 . . . ?
O10 Cu6 N6 C3 157.9(6) . . . . ?
N2 Cu1 N7 C6 -74(2) . . . . ?
O9 Cu1 N7 C6 -153.9(6) . . . . ?
N4 Cu1 N7 C6 52.3(6) . . . . ?
O1 Cu1 N7 C6 -30.6(6) . . . . ?
N2 Cu1 N7 N8 106.5(19) . . . . ?
O9 Cu1 N7 N8 26.8(3) . . . . ?
N4 Cu1 N7 N8 -127.0(3) . . . . ?
O1 Cu1 N7 N8 150.2(3) . . . . ?
C6 N7 N8 N9 0.3(6) . . . . ?
Cu1 N7 N8 N9 179.7(3) . . . . ?
C6 N7 N8 Cu3 177.5(4) . . . . ?
Cu1 N7 N8 Cu3 -3.0(5) . . . . ?
N8 Cu3 N8 N9 14(5) 2_565 . . . ?
O9 Cu3 N8 N9 -25.7(4) 2_565 . . . ?
O9 Cu3 N8 N9 154.3(4) . . . . ?
O5 Cu3 N8 N9 -127.7(4) . . . . ?
O5 Cu3 N8 N9 52.3(4) 2_565 . . . ?
N8 Cu3 N8 N7 -162(5) 2_565 . . . ?
O9 Cu3 N8 N7 157.6(4) 2_565 . . . ?
O9 Cu3 N8 N7 -22.4(4) . . . . ?
O5 Cu3 N8 N7 55.7(4) . . . . ?
O5 Cu3 N8 N7 -124.3(4) 2_565 . . . ?
N7 N8 N9 C5 -0.2(6) . . . . ?
Cu3 N8 N9 C5 -177.2(4) . . . . ?
N7 N8 N9 Cu2 178.8(3) . . . 2_565 ?
Cu3 N8 N9 Cu2 1.8(5) . . . 2_565 ?
O3 Cu6 N10 N11 -102.4(4) 1_655 . . . ?
N6 Cu6 N10 N11 -10(2) . . . . ?
O8 Cu6 N10 N11 113.6(4) 2_675 . . . ?
O10 Cu6 N10 N11 19.6(4) . . . . ?
O3 Cu6 N10 C8 64.9(7) 1_655 . . . ?
N6 Cu6 N10 C8 156.9(19) . . . . ?
O8 Cu6 N10 C8 -79.1(7) 2_675 . . . ?
O10 Cu6 N10 C8 -173.1(7) . . . . ?
C8 N10 N11 N12 -0.9(7) . . . . ?
Cu6 N10 N11 N12 169.8(4) . . . . ?
C8 N10 N11 Cu5 -173.2(5) . . . . ?
Cu6 N10 N11 Cu5 -2.5(6) . . . . ?
N11 Cu5 N11 N10 77(12) 2_666 . . . ?
O10 Cu5 N11 N10 161.2(5) 2_666 . . . ?
O10 Cu5 N11 N10 -18.8(5) . . . . ?
N11 Cu5 N11 N12 -94(12) 2_666 . . . ?
O10 Cu5 N11 N12 -10.2(5) 2_666 . . . ?
O10 Cu5 N11 N12 169.8(5) . . . . ?
N10 N11 N12 C7 1.3(7) . . . . ?
Cu5 N11 N12 C7 173.9(4) . . . . ?
N10 N11 N12 Cu4 179.0(4) . . . 2_666 ?
Cu5 N11 N12 Cu4 -8.4(6) . . . 2_666 ?
N2 N3 C1 C2 -0.5(7) . . . . ?
Cu4 N3 C1 C2 174.3(4) . . . . ?
N2 N1 C2 C1 0.0(6) . . . . ?
Cu2 N1 C2 C1 178.6(4) . . . . ?
N3 C1 C2 N1 0.4(7) . . . . ?
N5 N6 C3 C4 0.8(7) . . . . ?
Cu6 N6 C3 C4 -172.6(5) . . . . ?
N5 N4 C4 C3 0.2(7) . . . . ?
Cu1 N4 C4 C3 165.4(5) . . . . ?
N6 C3 C4 N4 -0.6(8) . . . . ?
N8 N9 C5 C6 0.1(6) . . . . ?
Cu2 N9 C5 C6 -178.6(4) 2_565 . . . ?
N8 N7 C6 C5 -0.2(6) . . . . ?
Cu1 N7 C6 C5 -179.5(4) . . . . ?
N9 C5 C6 N7 0.1(7) . . . . ?
N11 N12 C7 C8 -1.2(8) . . . . ?
Cu4 N12 C7 C8 -178.1(5) 2_666 . . . ?
N11 N10 C8 C7 0.1(8) . . . . ?
Cu6 N10 C8 C7 -168.1(5) . . . . ?
N12 C7 C8 N10 0.7(8) . . . . ?
C14 C9 C10 C11 1.0(8) . . . . ?
C15 C9 C10 C11 -174.6(5) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C9 C10 C11 C16 175.1(5) . . . . ?
C10 C11 C12 C13 -2.2(9) . . . . ?
C16 C11 C12 C13 -176.7(6) . . . . ?
C11 C12 C13 C14 2.4(9) . . . . ?
C10 C9 C14 C13 -0.9(8) . . . . ?
C15 C9 C14 C13 174.7(5) . . . . ?
C12 C13 C14 C9 -0.8(9) . . . . ?
Cu4 O1 C15 O2 -29.5(8) . . . . ?
Cu1 O1 C15 O2 118.1(5) . . . . ?
Cu4 O1 C15 C9 148.4(4) . . . . ?
Cu1 O1 C15 C9 -64.0(6) . . . . ?
C10 C9 C15 O2 170.4(5) . . . . ?
C14 C9 C15 O2 -5.0(8) . . . . ?
C10 C9 C15 O1 -7.5(7) . . . . ?
C14 C9 C15 O1 177.0(5) . . . . ?
Cu6 O3 C16 O4 18.2(7) 1_455 . . . ?
Cu6 O3 C16 C11 -158.5(4) 1_455 . . . ?
C10 C11 C16 O4 -142.5(6) . . . . ?
C12 C11 C16 O4 31.9(9) . . . . ?
C10 C11 C16 O3 34.4(8) . . . . ?
C12 C11 C16 O3 -151.1(6) . . . . ?
C22 C17 C18 C19 -0.3(8) . . . . ?
C23 C17 C18 C19 179.3(5) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C17 C18 C19 C24 178.6(5) . . . . ?
C18 C19 C20 C21 0.0(9) . . . . ?
C24 C19 C20 C21 -178.1(5) . . . . ?
C19 C20 C21 C22 -0.7(9) . . . . ?
C18 C17 C22 C21 -0.5(9) . . . . ?
C23 C17 C22 C21 179.9(5) . . . . ?
C20 C21 C22 C17 1.0(9) . . . . ?
Cu3 O5 C23 O6 45.8(8) . . . . ?
Cu3 O5 C23 C17 -134.2(4) . . . . ?
Cu2 O6 C23 O5 -3.5(8) . . . . ?
Cu2 O6 C23 C17 176.5(3) . . . . ?
C22 C17 C23 O5 8.4(8) . . . . ?
C18 C17 C23 O5 -171.2(5) . . . . ?
C22 C17 C23 O6 -171.6(5) . . . . ?
C18 C17 C23 O6 8.8(8) . . . . ?
Cu6 O8 C24 O7 -10.5(6) 2_675 . . . ?
Cu6 O8 C24 C19 167.7(4) 2_675 . . . ?
Cu2 O7 C24 O8 -176.2(4) 2_575 . . . ?
Cu2 O7 C24 C19 5.6(10) 2_575 . . . ?
C20 C19 C24 O8 -13.6(8) . . . . ?
C18 C19 C24 O8 168.3(5) . . . . ?
C20 C19 C24 O7 164.6(5) . . . . ?
C18 C19 C24 O7 -13.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.318
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_n130724a
_database_code_depnum_ccdc_archive 'CCDC 1013120'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cu5 N6 O14'
_chemical_formula_weight         886.12

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.3870(6)
_cell_length_b                   8.4427(7)
_cell_length_c                   10.0939(8)
_cell_angle_alpha                113.9400(10)
_cell_angle_beta                 94.1230(10)
_cell_angle_gamma                95.5090(10)
_cell_volume                     645.39(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             439
_exptl_absorpt_coefficient_mu    4.139
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5229
_exptl_absorpt_correction_T_max  0.5756
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3339
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2253
_reflns_number_gt                2088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0286P)²+0.7539P] 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         2253
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0553
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cu1 Cu 0.29259(4) 0.23314(4) 0.61551(3) 0.00782(10) Uani 1 1 d . . .
Cu2 Cu 0.11009(3) -0.14677(4) 0.49238(3) 0.00618(10) Uani 1 1 d . . .
Cu3 Cu 0.5000 0.5000 0.5000 0.00822(12) Uani 1 2 d S . .
O1 O 0.2919(2) -0.1598(2) 0.6178(2) 0.0097(4) Uani 1 1 d . . .
O2 O 0.4136(2) 0.1198(2) 0.71387(19) 0.0087(4) Uani 1 1 d . . .
O3 O 0.7382(2) 0.0653(2) 0.61454(19) 0.0097(4) Uani 1 1 d . . .
O4 O 0.8413(2) 0.2689(3) 0.8338(2) 0.0174(4) Uani 1 1 d . . .
O5 O 0.4870(2) 0.3591(2) 0.6066(2) 0.0121(4) Uani 1 1 d . . .
H5' H 0.5609 0.2975 0.6031 0.018 Uiso 1 1 d R . .
O6 O 0.0789(2) 0.1340(2) 0.62684(19) 0.0074(4) Uani 1 1 d . . .
H6' H 0.0627 0.1637 0.7143 0.011 Uiso 1 1 d R . .
O7W O 0.8311(3) 0.5149(3) 0.1250(2) 0.0268(5) Uani 1 1 d . . .
H7A H 0.8122 0.4349 0.0401 0.040 Uiso 1 1 d R . .
H7B H 0.9257 0.5658 0.1376 0.040 Uiso 1 1 d R . .
N1 N 0.2652(3) 0.4208(3) 0.4298(2) 0.0089(5) Uani 1 1 d . . .
N2 N 0.1873(2) 0.3268(3) 0.4889(2) 0.0088(5) Uani 1 1 d . . .
N3 N 0.0340(3) 0.2792(3) 0.4291(2) 0.0082(5) Uani 1 1 d . . .
C1 C 0.0143(3) 0.3455(3) 0.3290(3) 0.0090(5) Uani 1 1 d . . .
H1 H -0.0827 0.3326 0.2687 0.011 Uiso 1 1 calc R . .
C2 C 0.1598(3) 0.4348(3) 0.3302(3) 0.0091(5) Uani 1 1 d . . .
H2 H 0.1820 0.4958 0.2711 0.011 Uiso 1 1 calc R . .
C3 C 0.5299(3) -0.0823(3) 0.7814(3) 0.0074(5) Uani 1 1 d . . .
C4 C 0.6874(3) 0.0105(3) 0.8218(3) 0.0084(5) Uani 1 1 d . . .
C5 C 0.7913(3) -0.0170(4) 0.9209(3) 0.0111(6) Uani 1 1 d . . .
H5 H 0.8962 0.0483 0.9515 0.013 Uiso 1 1 calc R . .
C6 C 0.7452(3) -0.1382(4) 0.9768(3) 0.0141(6) Uani 1 1 d . . .
H6 H 0.8182 -0.1551 1.0448 0.017 Uiso 1 1 calc R . .
C7 C 0.5923(3) -0.2343(4) 0.9327(3) 0.0124(6) Uani 1 1 d . . .
H7 H 0.5608 -0.3192 0.9686 0.015 Uiso 1 1 calc R . .
C8 C 0.4863(3) -0.2054(3) 0.8361(3) 0.0100(5) Uani 1 1 d . . .
H8 H 0.3815 -0.2708 0.8064 0.012 Uiso 1 1 calc R . .
C9 C 0.4031(3) -0.0371(3) 0.6960(3) 0.0076(5) Uani 1 1 d . . .
C10 C 0.7575(3) 0.1276(3) 0.7541(3) 0.0087(5) 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 O5 1.8872(18) . ?
Cu1 O6 1.9353(17) . ?
Cu1 O2 1.9353(18) . ?
Cu1 N2 1.957(2) . ?
Cu2 O1 1.9516(18) . ?
Cu2 O6 1.9588(18) 2_556 ?
Cu2 O3 1.9722(17) 2_656 ?
Cu2 N3 1.984(2) 2_556 ?
Cu2 O6 2.2555(18) . ?
Cu3 O5 1.9019(19) 2_666 ?
Cu3 O5 1.9019(19) . ?
Cu3 N1 1.997(2) 2_666 ?
Cu3 N1 1.997(2) . ?
O1 C9 1.269(3) . ?
O2 C9 1.256(3) . ?
O3 C10 1.279(3) . ?
O3 Cu2 1.9722(17) 2_656 ?
O4 C10 1.242(3) . ?
O5 H5' 0.8399 . ?
O6 Cu2 1.9588(18) 2_556 ?
O6 H6' 0.8399 . ?
O7W H7A 0.8400 . ?
O7W H7B 0.8400 . ?
N1 N2 1.324(3) . ?
N1 C2 1.340(4) . ?
N2 N3 1.331(3) . ?
N3 C1 1.347(3) . ?
N3 Cu2 1.984(2) 2_556 ?
C1 C2 1.368(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C8 1.393(4) . ?
C3 C4 1.411(4) . ?
C3 C9 1.494(4) . ?
C4 C5 1.385(4) . ?
C4 C10 1.511(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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
O5 Cu1 O6 171.59(8) . . ?
O5 Cu1 O2 89.66(8) . . ?
O6 Cu1 O2 97.45(7) . . ?
O5 Cu1 N2 86.80(8) . . ?
O6 Cu1 N2 86.81(8) . . ?
O2 Cu1 N2 170.82(8) . . ?
O1 Cu2 O6 177.36(7) . 2_556 ?
O1 Cu2 O3 89.82(8) . 2_656 ?
O6 Cu2 O3 92.71(7) 2_556 2_656 ?
O1 Cu2 N3 89.01(8) . 2_556 ?
O6 Cu2 N3 88.69(8) 2_556 2_556 ?
O3 Cu2 N3 167.71(8) 2_656 2_556 ?
O1 Cu2 O6 97.47(7) . . ?
O6 Cu2 O6 81.79(7) 2_556 . ?
O3 Cu2 O6 89.04(7) 2_656 . ?
N3 Cu2 O6 103.24(8) 2_556 . ?
O5 Cu3 O5 180.0 2_666 . ?
O5 Cu3 N1 88.31(8) 2_666 2_666 ?
O5 Cu3 N1 91.69(8) . 2_666 ?
O5 Cu3 N1 91.69(8) 2_666 . ?
O5 Cu3 N1 88.31(8) . . ?
N1 Cu3 N1 180.0 2_666 . ?
C9 O1 Cu2 127.21(17) . . ?
C9 O2 Cu1 131.28(17) . . ?
C10 O3 Cu2 121.17(16) . 2_656 ?
Cu1 O5 Cu3 123.41(10) . . ?
Cu1 O5 H5' 107.8 . . ?
Cu3 O5 H5' 117.6 . . ?
Cu1 O6 Cu2 120.92(9) . 2_556 ?
Cu1 O6 Cu2 95.86(7) . . ?
Cu2 O6 Cu2 98.21(7) 2_556 . ?
Cu1 O6 H6' 110.5 . . ?
Cu2 O6 H6' 111.7 2_556 . ?
Cu2 O6 H6' 118.7 . . ?
H7A O7W H7B 109.3 . . ?
N2 N1 C2 107.6(2) . . ?
N2 N1 Cu3 116.67(17) . . ?
C2 N1 Cu3 135.69(18) . . ?
N1 N2 N3 110.1(2) . . ?
N1 N2 Cu1 124.18(17) . . ?
N3 N2 Cu1 124.66(17) . . ?
N2 N3 C1 107.3(2) . . ?
N2 N3 Cu2 117.43(17) . 2_556 ?
C1 N3 Cu2 135.18(18) . 2_556 ?
N3 C1 C2 107.3(2) . . ?
N3 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
N1 C2 C1 107.7(2) . . ?
N1 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
C8 C3 C4 119.2(2) . . ?
C8 C3 C9 118.9(2) . . ?
C4 C3 C9 121.5(2) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C10 116.6(2) . . ?
C3 C4 C10 124.4(2) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C3 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
O2 C9 O1 126.7(2) . . ?
O2 C9 C3 116.7(2) . . ?
O1 C9 C3 116.6(2) . . ?
O4 C10 O3 123.9(2) . . ?
O4 C10 C4 119.2(2) . . ?
O3 C10 C4 116.5(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
O6 Cu2 O1 C9 -105.7(15) 2_556 . . . ?
O3 Cu2 O1 C9 56.9(2) 2_656 . . . ?
N3 Cu2 O1 C9 -135.3(2) 2_556 . . . ?
O6 Cu2 O1 C9 -32.1(2) . . . . ?
O5 Cu1 O2 C9 -135.9(2) . . . . ?
O6 Cu1 O2 C9 48.6(2) . . . . ?
N2 Cu1 O2 C9 -68.6(6) . . . . ?
O6 Cu1 O5 Cu3 -40.3(6) . . . . ?
O2 Cu1 O5 Cu3 171.83(12) . . . . ?
N2 Cu1 O5 Cu3 0.30(12) . . . . ?
O5 Cu3 O5 Cu1 -81(15) 2_666 . . . ?
N1 Cu3 O5 Cu1 176.40(12) 2_666 . . . ?
N1 Cu3 O5 Cu1 -3.60(12) . . . . ?
O5 Cu1 O6 Cu2 47.0(6) . . . 2_556 ?
O2 Cu1 O6 Cu2 -165.44(10) . . . 2_556 ?
N2 Cu1 O6 Cu2 6.39(11) . . . 2_556 ?
O5 Cu1 O6 Cu2 150.2(5) . . . . ?
O2 Cu1 O6 Cu2 -62.21(8) . . . . ?
N2 Cu1 O6 Cu2 109.62(8) . . . . ?
O1 Cu2 O6 Cu1 60.11(8) . . . . ?
O6 Cu2 O6 Cu1 -122.46(10) 2_556 . . . ?
O3 Cu2 O6 Cu1 -29.58(8) 2_656 . . . ?
N3 Cu2 O6 Cu1 150.85(8) 2_556 . . . ?
O1 Cu2 O6 Cu2 -177.43(7) . . . 2_556 ?
O6 Cu2 O6 Cu2 0.0 2_556 . . 2_556 ?
O3 Cu2 O6 Cu2 92.88(8) 2_656 . . 2_556 ?
N3 Cu2 O6 Cu2 -86.69(9) 2_556 . . 2_556 ?
O5 Cu3 N1 N2 -172.69(18) 2_666 . . . ?
O5 Cu3 N1 N2 7.31(18) . . . . ?
N1 Cu3 N1 N2 -107(14) 2_666 . . . ?
O5 Cu3 N1 C2 9.3(3) 2_666 . . . ?
O5 Cu3 N1 C2 -170.7(3) . . . . ?
N1 Cu3 N1 C2 75(14) 2_666 . . . ?
C2 N1 N2 N3 0.3(3) . . . . ?
Cu3 N1 N2 N3 -178.22(15) . . . . ?
C2 N1 N2 Cu1 168.92(17) . . . . ?
Cu3 N1 N2 Cu1 -9.6(3) . . . . ?
O5 Cu1 N2 N1 5.84(19) . . . . ?
O6 Cu1 N2 N1 -179.6(2) . . . . ?
O2 Cu1 N2 N1 -61.6(6) . . . . ?
O5 Cu1 N2 N3 172.8(2) . . . . ?
O6 Cu1 N2 N3 -12.64(19) . . . . ?
O2 Cu1 N2 N3 105.4(5) . . . . ?
N1 N2 N3 C1 -0.1(3) . . . . ?
Cu1 N2 N3 C1 -168.65(17) . . . . ?
N1 N2 N3 Cu2 -176.98(15) . . . 2_556 ?
Cu1 N2 N3 Cu2 14.5(3) . . . 2_556 ?
N2 N3 C1 C2 -0.1(3) . . . . ?
Cu2 N3 C1 C2 175.94(19) 2_556 . . . ?
N2 N1 C2 C1 -0.4(3) . . . . ?
Cu3 N1 C2 C1 177.72(19) . . . . ?
N3 C1 C2 N1 0.3(3) . . . . ?
C8 C3 C4 C5 -3.4(4) . . . . ?
C9 C3 C4 C5 169.2(2) . . . . ?
C8 C3 C4 C10 170.9(2) . . . . ?
C9 C3 C4 C10 -16.5(4) . . . . ?
C3 C4 C5 C6 2.4(4) . . . . ?
C10 C4 C5 C6 -172.4(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -1.4(4) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C4 C3 C8 C7 2.1(4) . . . . ?
C9 C3 C8 C7 -170.7(2) . . . . ?
Cu1 O2 C9 O1 -10.1(4) . . . . ?
Cu1 O2 C9 C3 173.32(16) . . . . ?
Cu2 O1 C9 O2 4.0(4) . . . . ?
Cu2 O1 C9 C3 -179.43(15) . . . . ?
C8 C3 C9 O2 143.1(2) . . . . ?
C4 C3 C9 O2 -29.6(3) . . . . ?
C8 C3 C9 O1 -33.9(3) . . . . ?
C4 C3 C9 O1 153.5(2) . . . . ?
Cu2 O3 C10 O4 19.4(4) 2_656 . . . ?
Cu2 O3 C10 C4 -153.86(17) 2_656 . . . ?
C5 C4 C10 O4 -46.5(4) . . . . ?
C3 C4 C10 O4 139.1(3) . . . . ?
C5 C4 C10 O3 127.1(3) . . . . ?
C3 C4 C10 O3 -47.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.085
