# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Junfeng Bai'
'Baishu Zheng'
'Yizhi Li'
'Zhen Yang'
'Shuhua Li'
_publ_contact_author_name        'Junfeng Bai'
_publ_contact_author_email       bjunfeng@nju.edu.cn

data_840576
_database_code_depnum_ccdc_archive 'CCDC 840576'
#TrackingRef '- re-revised 840576.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 Cu N O6'
_chemical_formula_sum            'C17 H11 Cu N O6'
_chemical_formula_weight         388.81

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           cubic
_symmetry_space_group_name_H-M   fm-3m

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

_cell_length_a                   52.557(3)
_cell_length_b                   52.557(3)
_cell_length_c                   52.557(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     145177(13)
_cell_formula_units_Z            96
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4830
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      16.96

_exptl_crystal_description       polyhedra
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    0.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             18912
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9035
_exptl_absorpt_correction_T_max  0.9230
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(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  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            202502
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6764
_reflns_number_gt                4848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.006 -0.006 -0.009 112037 4315 ' '

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+1.9900P] where P=(Fo^2^+2Fc^2^)/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         6764
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.10211(3) 0.64877(3) 0.46553(3) 0.0436(4) Uani 1 1 d . . .
C2 C 0.06710(3) 0.65091(4) 0.43290(3) 0.0418(5) Uani 1 2 d S . .
H2 H 0.0600 0.6363 0.4400 0.050 Uiso 1 2 calc SR . .
C3 C 0.08857(3) 0.66167(3) 0.44392(3) 0.0486(4) Uani 1 1 d . . .
C4 C 0.09683(3) 0.68475(3) 0.43478(3) 0.0489(4) Uani 1 1 d . . .
H4 H 0.1107 0.6924 0.4427 0.059 Uiso 1 1 calc R . .
C5 C 0.08562(3) 0.69711(5) 0.41438(3) 0.0531(6) Uani 1 2 d S . .
C6 C 0.11192(5) 0.72390(6) 0.38808(5) 0.0690(8) Uani 1 2 d S . .
C7 C 0.11892(4) 0.75063(6) 0.38108(4) 0.0665(7) Uani 1 2 d S . .
C8 C 0.10193(8) 0.76665(8) 0.36966(8) 0.0643(10) Uani 0.50 1 d P . .
H8A H 0.0847 0.7613 0.3669 0.077 Uiso 0.50 1 d PR . .
C9 C 0.10930(9) 0.79103(9) 0.36138(8) 0.0748(12) Uani 0.50 1 d P . .
H9A H 0.0975 0.8024 0.3533 0.090 Uiso 0.50 1 d PR . .
C10 C 0.13502(4) 0.79832(5) 0.36498(4) 0.0637(7) Uani 1 2 d S . .
C11 C 0.15228(10) 0.78177(9) 0.37473(9) 0.0747(12) Uani 0.50 1 d P . .
H11A H 0.1698 0.7867 0.3762 0.090 Uiso 0.50 1 d PR . .
C12 C 0.14477(9) 0.75795(9) 0.38316(10) 0.0764(12) Uani 0.50 1 d P . .
H12A H 0.1570 0.7462 0.3900 0.092 Uiso 0.50 1 d PR . .
C13 C 0.14522(4) 0.82322(5) 0.35478(4) 0.0597(7) Uani 1 2 d S . .
C14 C 0.13351(5) 0.83420(4) 0.33420(4) 0.0630(7) Uani 1 2 d S . .
H14 H 0.1182 0.8279 0.3279 0.076 Uiso 1 2 calc SR . .
Cu1 Cu 0.107539(5) 0.607539(5) 0.5000 0.04263(12) Uani 1 4 d S . .
Cu2 Cu 0.143100(5) 0.643100(5) 0.5000 0.04535(12) Uani 1 4 d S . .
N1 N 0.09440(3) 0.72243(4) 0.40560(3) 0.0553(5) Uani 1 2 d S . .
H1 H 0.0880 0.7361 0.4120 0.066 Uiso 1 2 d SR . .
O1 O 0.091693(19) 0.628388(19) 0.473788(19) 0.0429(3) Uani 1 1 d . . .
O2 O 0.12219(2) 0.658495(19) 0.47378(2) 0.0480(3) Uani 1 1 d . . .
O3 O 0.12326(3) 0.70551(4) 0.37674(3) 0.0784(6) Uani 1 2 d S . .
O1W O 0.17155(3) 0.67155(3) 0.5000 0.0512(5) Uani 1 4 d S . .
H1W2 H 0.1876 0.6642 0.4957 0.077 Uiso 0.25 1 d PR . .
H1W3 H 0.1726 0.6793 0.5166 0.077 Uiso 0.25 1 d PR . .
O2W O 0.07888(3) 0.57888(3) 0.5000 0.0555(6) Uani 1 4 d S . .
H2W1 H 0.0831 0.5660 0.4877 0.083 Uiso 0.25 1 d PR . .
H2W2 H 0.0628 0.5863 0.4957 0.083 Uiso 0.25 1 d PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0515(9) 0.0434(8) 0.0358(7) 0.0049(6) -0.0024(7) -0.0117(7)
C2 0.0466(7) 0.0321(10) 0.0466(7) 0.0116(6) -0.0061(9) -0.0116(6)
C3 0.0517(9) 0.0466(9) 0.0475(9) 0.0097(7) -0.0086(7) -0.0110(7)
C4 0.0554(10) 0.0350(8) 0.0564(10) 0.0084(7) -0.0102(8) -0.0100(7)
C5 0.0479(8) 0.0634(15) 0.0479(8) 0.0194(8) -0.0068(10) -0.0194(8)
C6 0.0705(12) 0.0660(18) 0.0705(12) 0.0116(12) -0.0212(15) -0.0116(12)
C7 0.0599(10) 0.0796(19) 0.0599(10) 0.0156(10) -0.0045(13) -0.0156(10)
C8 0.061(2) 0.064(2) 0.068(3) -0.0048(19) -0.005(2) -0.0124(19)
C9 0.068(3) 0.089(3) 0.067(3) 0.024(2) -0.020(2) -0.020(2)
C10 0.0641(10) 0.0629(17) 0.0641(10) 0.0171(10) -0.0082(13) -0.0171(10)
C11 0.083(3) 0.074(3) 0.067(3) 0.006(2) -0.013(2) -0.015(2)
C12 0.063(3) 0.068(3) 0.098(3) 0.025(3) -0.001(2) -0.010(2)
C13 0.0508(8) 0.0775(18) 0.0508(8) 0.0190(9) -0.0128(11) -0.0190(9)
C14 0.0606(15) 0.0643(11) 0.0643(11) 0.0286(13) -0.0251(10) -0.0251(10)
Cu1 0.04430(15) 0.04430(15) 0.0393(2) 0.000 0.000 -0.01492(16)
Cu2 0.04516(16) 0.04516(16) 0.0457(2) 0.000 0.000 -0.01428(17)
N1 0.0592(8) 0.0475(11) 0.0592(8) 0.0180(7) -0.0272(11) -0.0180(7)
O1 0.0419(6) 0.0479(6) 0.0390(6) -0.0030(4) 0.0004(4) -0.0146(5)
O2 0.0515(6) 0.0356(5) 0.0568(7) 0.0026(5) -0.0038(5) -0.0108(5)
O3 0.0797(9) 0.0758(14) 0.0797(9) 0.0056(9) -0.0158(11) -0.0056(9)
O1W 0.0438(8) 0.0438(8) 0.0661(15) 0.000 0.000 -0.0177(10)
O2W 0.0538(8) 0.0538(8) 0.0589(14) 0.000 0.000 -0.0211(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.2502(18) . ?
C1 O1 1.2789(17) . ?
C1 C3 1.502(2) . ?
C2 C3 1.3886(18) . ?
C2 C3 1.3886(18) 166 ?
C2 H2 0.9300 . ?
C3 C4 1.375(2) . ?
C4 C5 1.3851(19) . ?
C4 H4 0.9300 . ?
C5 C4 1.3852(19) 166 ?
C5 N1 1.482(3) . ?
C6 O3 1.282(4) . ?
C6 N1 1.305(4) . ?
C6 C7 1.498(4) . ?
C7 C8 1.366(5) 166 ?
C7 C8 1.366(4) . ?
C7 C12 1.416(5) 166 ?
C7 C12 1.416(5) . ?
C8 C12 1.182(6) 166 ?
C8 C9 1.407(6) . ?
C8 C11 1.862(7) 166 ?
C8 H8A 0.9599 . ?
C9 C11 1.207(6) 166 ?
C9 C10 1.418(4) . ?
C9 C12 1.812(7) 166 ?
C9 H9A 0.9600 . ?
C10 C11 1.357(5) . ?
C10 C11 1.357(5) 166 ?
C10 C9 1.418(4) 166 ?
C10 C13 1.512(3) . ?
C11 C9 1.206(6) 166 ?
C11 C12 1.386(6) . ?
C11 C8 1.862(7) 166 ?
C11 C11 2.007(9) 166 ?
C11 H11A 0.9599 . ?
C12 C8 1.182(6) 166 ?
C12 C9 1.812(7) 166 ?
C12 H12A 0.9595 . ?
C13 C14 1.3718(17) . ?
C13 C14 1.3719(17) 34_655 ?
C14 C13 1.3718(17) 55_564 ?
C14 H14 0.9300 . ?
Cu1 O1 1.9473(11) . ?
Cu1 O1 1.9475(11) 85_456 ?
Cu1 O1 1.9475(11) 98_556 ?
Cu1 O1 1.9475(11) 182_455 ?
Cu1 O2W 2.130(2) . ?
Cu1 Cu2 2.6431(5) . ?
Cu2 O2 1.9394(11) 98_556 ?
Cu2 O2 1.9394(11) 182_455 ?
Cu2 O2 1.9394(11) 85_456 ?
Cu2 O2 1.9394(11) . ?
Cu2 O1W 2.1150(19) . ?
N1 H1 0.8604 . ?
O1W H1W2 0.9568 . ?
O1W H1W3 0.9632 . ?
O2W H2W1 0.9613 . ?
O2W H2W2 0.9595 . ?

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
O2 C1 O1 125.88(14) . . ?
O2 C1 C3 118.54(13) . . ?
O1 C1 C3 115.58(13) . . ?
C3 C2 C3 120.79(19) . 166 ?
C3 C2 H2 119.6 . . ?
C3 C2 H2 119.6 166 . ?
C4 C3 C2 118.04(15) . . ?
C4 C3 C1 120.84(14) . . ?
C2 C3 C1 121.11(14) . . ?
C3 C4 C5 123.37(16) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C4 116.0(2) . 166 ?
C4 C5 N1 121.99(10) . . ?
C4 C5 N1 121.99(10) 166 . ?
O3 C6 N1 127.7(3) . . ?
O3 C6 C7 118.6(3) . . ?
N1 C6 C7 113.7(3) . . ?
C8 C7 C8 101.2(4) 166 . ?
C8 C7 C12 119.6(3) 166 166 ?
C8 C7 C12 50.3(3) . 166 ?
C8 C7 C12 50.3(3) 166 . ?
C8 C7 C12 119.6(3) . . ?
C12 C7 C12 94.3(4) 166 . ?
C8 C7 C6 121.7(2) 166 . ?
C8 C7 C6 121.7(2) . . ?
C12 C7 C6 118.1(3) 166 . ?
C12 C7 C6 118.1(3) . . ?
C12 C8 C7 67.1(3) 166 . ?
C12 C8 C9 88.4(4) 166 . ?
C7 C8 C9 121.1(4) . . ?
C12 C8 C11 48.0(3) 166 166 ?
C7 C8 C11 96.0(3) . 166 ?
C9 C8 C11 40.4(3) . 166 ?
C12 C8 H8A 114.5 166 . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 118.6 . . ?
C11 C8 H8A 130.7 166 . ?
C11 C9 C8 90.5(5) 166 . ?
C11 C9 C10 61.6(3) 166 . ?
C8 C9 C10 117.9(4) . . ?
C11 C9 C12 49.9(3) 166 166 ?
C8 C9 C12 40.7(3) . 166 ?
C10 C9 C12 94.3(4) . 166 ?
C11 C9 H9A 116.0 166 . ?
C8 C9 H9A 121.7 . . ?
C10 C9 H9A 120.4 . . ?
C12 C9 H9A 131.4 166 . ?
C11 C10 C11 95.4(4) . 166 ?
C11 C10 C9 51.5(3) . 166 ?
C11 C10 C9 120.9(3) 166 166 ?
C11 C10 C9 120.9(3) . . ?
C11 C10 C9 51.5(3) 166 . ?
C9 C10 C9 100.5(4) 166 . ?
C11 C10 C13 116.9(3) . . ?
C11 C10 C13 116.9(3) 166 . ?
C9 C10 C13 121.6(2) 166 . ?
C9 C10 C13 121.6(2) . . ?
C9 C11 C10 66.9(4) 166 . ?
C9 C11 C12 88.4(4) 166 . ?
C10 C11 C12 120.6(4) . . ?
C9 C11 C8 49.1(3) 166 166 ?
C10 C11 C8 96.2(3) . 166 ?
C12 C11 C8 39.4(3) . 166 ?
C9 C11 C11 94.1(3) 166 166 ?
C10 C11 C11 42.3(2) . 166 ?
C12 C11 C11 91.4(3) . 166 ?
C8 C11 C11 91.61(18) 166 166 ?
C9 C11 H11A 113.9 166 . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 119.3 . . ?
C8 C11 H11A 130.9 166 . ?
C11 C11 H11A 137.5 166 . ?
C8 C12 C11 92.6(5) 166 . ?
C8 C12 C7 62.7(3) 166 . ?
C11 C12 C7 119.6(4) . . ?
C8 C12 C9 50.9(3) 166 166 ?
C11 C12 C9 41.7(3) . 166 ?
C7 C12 C9 96.1(3) . 166 ?
C8 C12 H12A 115.5 166 . ?
C11 C12 H12A 120.5 . . ?
C7 C12 H12A 119.9 . . ?
C9 C12 H12A 130.8 166 . ?
C14 C13 C14 122.0(3) . 34_655 ?
C14 C13 C10 118.98(13) . . ?
C14 C13 C10 118.97(13) 34_655 . ?
C13 C14 C13 117.5(2) . 55_564 ?
C13 C14 H14 121.2 . . ?
C13 C14 H14 121.2 55_564 . ?
O1 Cu1 O1 169.05(6) . 85_456 ?
O1 Cu1 O1 90.06(6) . 98_556 ?
O1 Cu1 O1 88.90(6) 85_456 98_556 ?
O1 Cu1 O1 88.90(6) . 182_455 ?
O1 Cu1 O1 90.06(6) 85_456 182_455 ?
O1 Cu1 O1 169.05(6) 98_556 182_455 ?
O1 Cu1 O2W 95.48(3) . . ?
O1 Cu1 O2W 95.47(3) 85_456 . ?
O1 Cu1 O2W 95.47(3) 98_556 . ?
O1 Cu1 O2W 95.47(3) 182_455 . ?
O1 Cu1 Cu2 84.52(3) . . ?
O1 Cu1 Cu2 84.53(3) 85_456 . ?
O1 Cu1 Cu2 84.53(3) 98_556 . ?
O1 Cu1 Cu2 84.53(3) 182_455 . ?
O2W Cu1 Cu2 180.00(6) . . ?
O2 Cu2 O2 167.85(6) 98_556 182_455 ?
O2 Cu2 O2 88.18(7) 98_556 85_456 ?
O2 Cu2 O2 90.54(7) 182_455 85_456 ?
O2 Cu2 O2 90.54(7) 98_556 . ?
O2 Cu2 O2 88.17(7) 182_455 . ?
O2 Cu2 O2 167.86(6) 85_456 . ?
O2 Cu2 O1W 96.07(3) 98_556 . ?
O2 Cu2 O1W 96.07(3) 182_455 . ?
O2 Cu2 O1W 96.07(3) 85_456 . ?
O2 Cu2 O1W 96.07(3) . . ?
O2 Cu2 Cu1 83.93(3) 98_556 . ?
O2 Cu2 Cu1 83.93(3) 182_455 . ?
O2 Cu2 Cu1 83.93(3) 85_456 . ?
O2 Cu2 Cu1 83.93(3) . . ?
O1W Cu2 Cu1 180.00(5) . . ?
C6 N1 C5 119.5(2) . . ?
C6 N1 H1 120.2 . . ?
C5 N1 H1 120.3 . . ?
C1 O1 Cu1 121.89(10) . . ?
C1 O2 Cu2 123.66(9) . . ?
Cu2 O1W H1W2 109.9 . . ?
Cu2 O1W H1W3 109.7 . . ?
H1W2 O1W H1W3 109.5 . . ?
Cu1 O2W H2W1 109.5 . . ?
Cu1 O2W H2W2 109.6 . . ?
H2W1 O2W H2W2 109.4 . . ?

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
C3 C2 C3 C4 7.3(4) 166 . . . ?
C3 C2 C3 C1 -173.89(14) 166 . . . ?
O2 C1 C3 C4 -5.3(3) . . . . ?
O1 C1 C3 C4 174.85(16) . . . . ?
O2 C1 C3 C2 175.88(18) . . . . ?
O1 C1 C3 C2 -3.9(3) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C1 C3 C4 C5 177.8(2) . . . . ?
C3 C4 C5 C4 -0.4(4) . . . 166 ?
C3 C4 C5 N1 177.7(2) . . . . ?
O3 C6 C7 C8 -114.7(3) . . . 166 ?
N1 C6 C7 C8 65.3(3) . . . 166 ?
O3 C6 C7 C8 114.7(3) . . . . ?
N1 C6 C7 C8 -65.3(3) . . . . ?
O3 C6 C7 C12 56.2(3) . . . 166 ?
N1 C6 C7 C12 -123.8(3) . . . 166 ?
O3 C6 C7 C12 -56.2(3) . . . . ?
N1 C6 C7 C12 123.8(3) . . . . ?
C8 C7 C8 C12 119.3(3) 166 . . 166 ?
C12 C7 C8 C12 68.9(5) . . . 166 ?
C6 C7 C8 C12 -101.9(4) . . . 166 ?
C8 C7 C8 C9 46.3(6) 166 . . . ?
C12 C7 C8 C9 -73.0(5) 166 . . . ?
C12 C7 C8 C9 -4.2(7) . . . . ?
C6 C7 C8 C9 -175.0(4) . . . . ?
C8 C7 C8 C11 80.1(4) 166 . . 166 ?
C12 C7 C8 C11 -39.2(3) 166 . . 166 ?
C12 C7 C8 C11 29.6(5) . . . 166 ?
C6 C7 C8 C11 -141.2(3) . . . 166 ?
C12 C8 C9 C11 -3.2(4) 166 . . 166 ?
C7 C8 C9 C11 58.6(5) . . . 166 ?
C12 C8 C9 C10 -61.0(5) 166 . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C11 C8 C9 C10 -57.8(4) 166 . . . ?
C7 C8 C9 C12 61.8(4) . . . 166 ?
C11 C8 C9 C12 3.2(4) 166 . . 166 ?
C11 C9 C10 C11 -70.3(5) 166 . . . ?
C8 C9 C10 C11 3.8(7) . . . . ?
C12 C9 C10 C11 -31.1(5) 166 . . . ?
C8 C9 C10 C11 74.1(5) . . . 166 ?
C12 C9 C10 C11 39.2(3) 166 . . 166 ?
C11 C9 C10 C9 -121.4(4) 166 . . 166 ?
C8 C9 C10 C9 -47.3(7) . . . 166 ?
C12 C9 C10 C9 -82.2(4) 166 . . 166 ?
C11 C9 C10 C13 100.8(4) 166 . . . ?
C8 C9 C10 C13 174.9(3) . . . . ?
C12 C9 C10 C13 140.0(3) 166 . . . ?
C11 C10 C11 C9 -125.8(3) 166 . . 166 ?
C9 C10 C11 C9 -78.1(5) . . . 166 ?
C13 C10 C11 C9 110.4(4) . . . 166 ?
C11 C10 C11 C12 -52.6(7) 166 . . . ?
C9 C10 C11 C12 73.2(5) 166 . . . ?
C9 C10 C11 C12 -4.8(7) . . . . ?
C13 C10 C11 C12 -176.4(4) . . . . ?
C11 C10 C11 C8 -85.5(4) 166 . . 166 ?
C9 C10 C11 C8 40.3(3) 166 . . 166 ?
C9 C10 C11 C8 -37.8(5) . . . 166 ?
C13 C10 C11 C8 150.7(2) . . . 166 ?
C9 C10 C11 C11 125.8(3) 166 . . 166 ?
C9 C10 C11 C11 47.7(3) . . . 166 ?
C13 C10 C11 C11 -123.8(4) . . . 166 ?
C9 C11 C12 C8 3.3(4) 166 . . 166 ?
C10 C11 C12 C8 -58.5(6) . . . 166 ?
C11 C11 C12 C8 -90.8(3) 166 . . 166 ?
C9 C11 C12 C7 63.1(5) 166 . . . ?
C10 C11 C12 C7 1.3(8) . . . . ?
C8 C11 C12 C7 59.8(4) 166 . . . ?
C11 C11 C12 C7 -31.0(4) 166 . . . ?
C10 C11 C12 C9 -61.7(5) . . . 166 ?
C8 C11 C12 C9 -3.3(4) 166 . . 166 ?
C11 C11 C12 C9 -94.1(3) 166 . . 166 ?
C8 C7 C12 C8 79.6(5) . . . 166 ?
C12 C7 C12 C8 125.6(3) 166 . . 166 ?
C6 C7 C12 C8 -109.3(4) . . . 166 ?
C8 C7 C12 C11 -76.4(5) 166 . . . ?
C8 C7 C12 C11 3.2(7) . . . . ?
C12 C7 C12 C11 49.2(7) 166 . . . ?
C6 C7 C12 C11 174.3(4) . . . . ?
C8 C7 C12 C9 -39.8(3) 166 . . 166 ?
C8 C7 C12 C9 39.8(5) . . . 166 ?
C12 C7 C12 C9 85.8(4) 166 . . 166 ?
C6 C7 C12 C9 -149.1(3) . . . 166 ?
C11 C10 C13 C14 146.2(3) . . . . ?
C11 C10 C13 C14 34.2(5) 166 . . . ?
C9 C10 C13 C14 -154.4(4) 166 . . . ?
C9 C10 C13 C14 -25.3(5) . . . . ?
C11 C10 C13 C14 -34.2(5) . . . 34_655 ?
C11 C10 C13 C14 -146.2(3) 166 . . 34_655 ?
C9 C10 C13 C14 25.3(5) 166 . . 34_655 ?
C9 C10 C13 C14 154.3(4) . . . 34_655 ?
C14 C13 C14 C13 9.2(6) 34_655 . . 55_564 ?
C10 C13 C14 C13 -171.1(2) . . . 55_564 ?
O1 Cu1 Cu2 O2 90.89(5) . . . 98_556 ?
O1 Cu1 Cu2 O2 -89.11(5) 85_456 . . 98_556 ?
O1 Cu1 Cu2 O2 0.31(5) 98_556 . . 98_556 ?
O1 Cu1 Cu2 O2 -179.69(5) 182_455 . . 98_556 ?
O2W Cu1 Cu2 O2 -134(100) . . . 98_556 ?
O1 Cu1 Cu2 O2 -89.11(5) . . . 182_455 ?
O1 Cu1 Cu2 O2 90.89(5) 85_456 . . 182_455 ?
O1 Cu1 Cu2 O2 -179.69(5) 98_556 . . 182_455 ?
O1 Cu1 Cu2 O2 0.31(5) 182_455 . . 182_455 ?
O2W Cu1 Cu2 O2 46(100) . . . 182_455 ?
O1 Cu1 Cu2 O2 179.69(5) . . . 85_456 ?
O1 Cu1 Cu2 O2 -0.31(5) 85_456 . . 85_456 ?
O1 Cu1 Cu2 O2 89.11(5) 98_556 . . 85_456 ?
O1 Cu1 Cu2 O2 -90.89(5) 182_455 . . 85_456 ?
O2W Cu1 Cu2 O2 -46(100) . . . 85_456 ?
O1 Cu1 Cu2 O2 -0.31(5) . . . . ?
O1 Cu1 Cu2 O2 179.69(5) 85_456 . . . ?
O1 Cu1 Cu2 O2 -90.89(5) 98_556 . . . ?
O1 Cu1 Cu2 O2 89.11(5) 182_455 . . . ?
O2W Cu1 Cu2 O2 134(100) . . . . ?
O1 Cu1 Cu2 O1W 45(100) . . . . ?
O1 Cu1 Cu2 O1W -135(100) 85_456 . . . ?
O1 Cu1 Cu2 O1W -45(100) 98_556 . . . ?
O1 Cu1 Cu2 O1W 135(100) 182_455 . . . ?
O2W Cu1 Cu2 O1W 0(10) . . . . ?
O3 C6 N1 C5 0.000(2) . . . . ?
C7 C6 N1 C5 180.000(1) . . . . ?
C4 C5 N1 C6 91.0(2) . . . . ?
C4 C5 N1 C6 -91.0(2) 166 . . . ?
O2 C1 O1 Cu1 -4.3(2) . . . . ?
C3 C1 O1 Cu1 175.46(11) . . . . ?
O1 Cu1 O1 C1 2.22(11) 85_456 . . . ?
O1 Cu1 O1 C1 86.71(12) 98_556 . . . ?
O1 Cu1 O1 C1 -82.39(12) 182_455 . . . ?
O2W Cu1 O1 C1 -177.78(11) . . . . ?
Cu2 Cu1 O1 C1 2.22(11) . . . . ?
O1 C1 O2 Cu2 4.0(2) . . . . ?
C3 C1 O2 Cu2 -175.81(11) . . . . ?
O2 Cu2 O2 C1 -85.40(13) 98_556 . . . ?
O2 Cu2 O2 C1 82.52(13) 182_455 . . . ?
O2 Cu2 O2 C1 -1.55(12) 85_456 . . . ?
O1W Cu2 O2 C1 178.43(13) . . . . ?
Cu1 Cu2 O2 C1 -1.57(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.024