# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Co N3 O8'
_chemical_formula_weight         408.17

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C2/m  '

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

_cell_length_a                   14.462(2)
_cell_length_b                   15.486(3)
_cell_length_c                   7.4899(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.971(3)
_cell_angle_gamma                90.00
_cell_volume                     1665.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    533
_cell_measurement_theta_min      2.630
_cell_measurement_theta_max      19.305

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7346
_exptl_absorpt_correction_T_max  0.7713
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4251
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.10
_reflns_number_total             1538
_reflns_number_gt                1105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1026P)²+2.8144P] 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         1538
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Co1 Co 0.0000 0.5000 0.5000 0.0286(4) Uani 1 4 d S . .
Co2 Co 0.0000 0.0000 0.0000 0.0394(5) Uani 1 4 d S . .
O1 O -0.0678(3) 0.3501(3) 0.1870(7) 0.0641(15) Uani 1 1 d . . .
O2 O 0.0566(3) 0.4055(3) 0.3484(7) 0.0560(13) Uani 1 1 d . . .
O3 O 0.0740(3) 0.0977(2) -0.1085(5) 0.0419(10) Uani 1 1 d . . .
O4 O 0.1292(3) 0.5000 0.6724(7) 0.0409(14) Uani 1 2 d S . .
N1 N 0.0820(6) 0.0000 0.2538(10) 0.052(2) Uani 1 2 d S . .
N2 N 0.1051(3) 0.1569(3) 0.0140(6) 0.0346(11) Uani 1 1 d . . .
C1 C 0.0159(4) 0.3509(4) 0.2461(8) 0.0403(14) Uani 1 1 d . . .
C2 C 0.0787(4) 0.2801(3) 0.1861(7) 0.0332(12) Uani 1 1 d . . .
C3 C 0.1692(4) 0.2736(4) 0.2697(8) 0.0435(15) Uani 1 1 d . . .
H3 H 0.1907 0.3125 0.3599 0.052 Uiso 1 1 calc R . .
C4 C 0.2273(4) 0.2103(4) 0.2204(8) 0.0454(15) Uani 1 1 d . . .
H4 H 0.2887 0.2073 0.2736 0.054 Uiso 1 1 calc R . .
C5 C 0.1937(4) 0.1512(4) 0.0916(8) 0.0451(15) Uani 1 1 d . . .
H5 H 0.2322 0.1074 0.0583 0.054 Uiso 1 1 calc R . .
C6 C 0.0470(3) 0.2214(3) 0.0540(7) 0.0315(12) Uani 1 1 d . . .
C7 C 0.1253(9) 0.0000 0.3881(19) 0.076(3) Uani 1 2 d S . .
C8 C 0.1888(12) 0.0000 0.5661(16) 0.123(6) Uani 1 2 d S . .
H8A H 0.2503 0.0178 0.5458 0.148 Uiso 0.50 1 d PR . .
H8B H 0.1915 -0.0571 0.6163 0.148 Uiso 0.50 1 d PR . .
H8C H 0.1648 0.0393 0.6482 0.148 Uiso 0.50 1 d PR . .
O5 O 0.3335(6) 0.0000 0.9157(13) 0.097(3) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 2.080(4) . ?
Co1 O2 2.080(4) 5_566 ?
Co1 O2 2.080(4) 6_565 ?
Co1 O2 2.080(4) 2_556 ?
Co1 O4 2.138(5) . ?
Co1 O4 2.138(5) 5_566 ?
Co2 O3 2.075(4) 5 ?
Co2 O3 2.075(4) 6 ?
Co2 O3 2.075(4) 2 ?
Co2 O3 2.075(4) . ?
Co2 N1 2.115(8) . ?
Co2 N1 2.115(8) 5 ?
O1 C1 1.237(7) . ?
O2 C1 1.241(7) . ?
O3 N2 1.336(6) . ?
N1 C7 1.119(14) . ?
N2 C5 1.345(7) . ?
N2 C6 1.361(7) . ?
C1 C2 1.525(7) . ?
C2 C6 1.381(7) . ?
C2 C3 1.384(7) . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.496(10) 2 ?
C7 C8 1.524(19) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9601 . ?

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 Co1 O2 180 . 5_566 ?
O2 Co1 O2 89.4(3) . 6_565 ?
O2 Co1 O2 90.6(3) 5_566 6_565 ?
O2 Co1 O2 90.6(3) . 2_556 ?
O2 Co1 O2 89.4(3) 5_566 2_556 ?
O2 Co1 O2 180 6_565 2_556 ?
O2 Co1 O4 87.52(16) . . ?
O2 Co1 O4 92.48(16) 5_566 . ?
O2 Co1 O4 87.52(16) 6_565 . ?
O2 Co1 O4 92.48(16) 2_556 . ?
O2 Co1 O4 92.48(16) . 5_566 ?
O2 Co1 O4 87.52(16) 5_566 5_566 ?
O2 Co1 O4 92.48(15) 6_565 5_566 ?
O2 Co1 O4 87.52(16) 2_556 5_566 ?
O4 Co1 O4 180 . 5_566 ?
O3 Co2 O3 86.4(2) 5 6 ?
O3 Co2 O3 93.6(2) 5 2 ?
O3 Co2 O3 180 6 2 ?
O3 Co2 O3 180 5 . ?
O3 Co2 O3 93.6(2) 6 . ?
O3 Co2 O3 86.4(2) 2 . ?
O3 Co2 N1 84.69(18) 5 . ?
O3 Co2 N1 95.31(18) 6 . ?
O3 Co2 N1 84.69(18) 2 . ?
O3 Co2 N1 95.31(18) . . ?
O3 Co2 N1 95.31(18) 5 5 ?
O3 Co2 N1 84.69(18) 6 5 ?
O3 Co2 N1 95.31(18) 2 5 ?
O3 Co2 N1 84.69(18) . 5 ?
N1 Co2 N1 180 . 5 ?
C1 O2 Co1 128.9(4) . . ?
N2 O3 Co2 112.2(3) . . ?
C7 N1 Co2 180 . . ?
O3 N2 C5 118.4(5) . . ?
O3 N2 C6 119.3(4) . . ?
C5 N2 C6 122.2(5) . . ?
O1 C1 O2 126.7(5) . . ?
O1 C1 C2 118.6(5) . . ?
O2 C1 C2 114.6(5) . . ?
C6 C2 C3 119.3(5) . . ?
C6 C2 C1 121.8(5) . . ?
C3 C2 C1 118.9(5) . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.3(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N2 C5 C4 119.8(5) . . ?
N2 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N2 C6 C2 118.8(5) . . ?
N2 C6 C6 115.2(4) . 2 ?
C2 C6 C6 126.0(4) . 2 ?
N1 C7 C8 177.1(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
O2 Co1 O2 C1 -115.7(5) 6_565 . . . ?
O2 Co1 O2 C1 64.3(5) 2_556 . . . ?
O4 Co1 O2 C1 156.8(6) . . . . ?
O4 Co1 O2 C1 -23.2(6) 5_566 . . . ?
O3 Co2 O3 N2 -130.4(3) 6 . . . ?
O3 Co2 O3 N2 49.6(3) 2 . . . ?
N1 Co2 O3 N2 -34.8(4) . . . . ?
N1 Co2 O3 N2 145.2(4) 5 . . . ?
Co2 O3 N2 C5 98.0(5) . . . . ?
Co2 O3 N2 C6 -83.1(5) . . . . ?
Co1 O2 C1 O1 13.7(10) . . . . ?
Co1 O2 C1 C2 -168.2(4) . . . . ?
O1 C1 C2 C6 7.1(9) . . . . ?
O2 C1 C2 C6 -171.1(5) . . . . ?
O1 C1 C2 C3 -171.3(6) . . . . ?
O2 C1 C2 C3 10.4(8) . . . . ?
C6 C2 C3 C4 0.9(9) . . . . ?
C1 C2 C3 C4 179.3(6) . . . . ?
C2 C3 C4 C5 -2.4(9) . . . . ?
O3 N2 C5 C4 -178.9(5) . . . . ?
C6 N2 C5 C4 2.2(8) . . . . ?
C3 C4 C5 N2 0.9(9) . . . . ?
O3 N2 C6 C2 177.4(4) . . . . ?
C5 N2 C6 C2 -3.7(8) . . . . ?
O3 N2 C6 C6 -2.9(7) . . . 2 ?
C5 N2 C6 C6 175.9(5) . . . 2 ?
C3 C2 C6 N2 2.1(8) . . . . ?
C1 C2 C6 N2 -176.3(5) . . . . ?
C3 C2 C6 C6 -177.5(5) . . . 2 ?
C1 C2 C6 C6 4.1(9) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.106
_database_code_depnum_ccdc_archive 'CCDC 1018472'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Cu N2 O7'
_chemical_formula_weight         355.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.8488(13)
_cell_length_b                   16.227(4)
_cell_length_c                   13.164(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.507(3)
_cell_angle_gamma                90.00
_cell_volume                     1249.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2019
_cell_measurement_theta_min      3.096
_cell_measurement_theta_max      26.473

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6157
_exptl_absorpt_correction_T_max  0.6532
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6642
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2425
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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. 
During the refinement, the restrained command ISOR was utilized to restrain the non-H atom O2 with ADP.
;

_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)+(0.1259P)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         2425
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.103
_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
C1 C 0.1780(8) 0.3602(3) 0.7066(4) 0.0283(11) Uani 1 1 d . . .
H1 H 0.0674 0.3596 0.6545 0.034 Uiso 1 1 calc R . .
C2 C 0.2054(9) 0.4279(3) 0.7661(4) 0.0321(12) Uani 1 1 d . . .
H2 H 0.1124 0.4737 0.7552 0.039 Uiso 1 1 calc R . .
C3 C 0.3715(9) 0.4290(3) 0.8431(4) 0.0267(11) Uani 1 1 d . . .
H3 H 0.3940 0.4762 0.8822 0.032 Uiso 1 1 calc R . .
C4 C 0.5036(8) 0.3599(3) 0.8616(3) 0.0183(9) Uani 1 1 d . . .
C5 C 0.4645(7) 0.2899(3) 0.8014(3) 0.0162(9) Uani 1 1 d . . .
C6 C 0.5826(8) 0.2090(3) 0.8173(3) 0.0161(9) Uani 1 1 d . . .
C7 C 0.5357(8) 0.1524(3) 0.8942(3) 0.0173(9) Uani 1 1 d . . .
C8 C 0.6756(8) 0.0835(3) 0.9035(4) 0.0249(11) Uani 1 1 d . . .
H8 H 0.6480 0.0444 0.9534 0.030 Uiso 1 1 calc R . .
C9 C 0.8569(9) 0.0729(3) 0.8385(4) 0.0291(11) Uani 1 1 d . . .
H9 H 0.9563 0.0286 0.8476 0.035 Uiso 1 1 calc R . .
C10 C 0.8892(8) 0.1281(3) 0.7606(4) 0.0261(11) Uani 1 1 d . . .
H10 H 1.0073 0.1207 0.7156 0.031 Uiso 1 1 calc R . .
C11 C 0.6832(10) 0.3605(3) 0.9467(4) 0.0277(11) Uani 1 1 d . . .
C12 C 0.3403(8) 0.1652(3) 0.9666(3) 0.0190(10) Uani 1 1 d . . .
Cu1 Cu 1.04061(9) 0.27523(4) 1.06194(4) 0.0193(3) Uani 1 1 d . . .
N1 N 0.3113(6) 0.2942(2) 0.7232(3) 0.0184(8) Uani 1 1 d . . .
N2 N 0.7464(6) 0.1930(2) 0.7507(3) 0.0179(8) Uani 1 1 d . . .
O1 O 0.8179(6) 0.3012(2) 0.9510(3) 0.0229(7) Uani 1 1 d . . .
O2 O 0.6832(11) 0.4203(3) 1.0047(4) 0.087(2) Uani 1 1 d U . .
O3 O 0.2487(6) 0.2362(2) 0.9614(3) 0.0288(9) Uani 1 1 d . . .
O4 O 0.2913(6) 0.1087(2) 1.0236(3) 0.0329(9) Uani 1 1 d . . .
O5 O 0.2929(6) 0.2283(2) 0.6609(3) 0.0239(8) Uani 1 1 d . . .
O6 O 0.7700(6) 0.2458(2) 0.6714(3) 0.0232(7) Uani 1 1 d . . .
O7 O 1.1104(9) 0.4172(3) 1.0882(4) 0.0602(14) Uani 1 1 d . . .
H7A H 1.2099 0.4547 1.0779 0.090 Uiso 1 1 d R . .
H7B H 0.9964 0.4171 1.0459 0.090 Uiso 1 1 d R . .


_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 N1 1.340(6) . ?
C1 C2 1.356(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(6) . ?
C4 C11 1.515(6) . ?
C5 N1 1.348(6) . ?
C5 C6 1.496(6) . ?
C6 N2 1.341(6) . ?
C6 C7 1.399(6) . ?
C7 C8 1.389(6) . ?
C7 C12 1.522(6) . ?
C8 C9 1.391(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.348(6) . ?
C10 H10 0.9300 . ?
C11 O2 1.236(6) . ?
C11 O1 1.244(6) . ?
C12 O4 1.224(6) . ?
C12 O3 1.271(6) . ?
Cu1 O3 1.929(4) 1_655 ?
Cu1 O6 1.973(3) 4_666 ?
Cu1 O5 1.974(3) 4_666 ?
Cu1 O1 1.977(3) . ?
Cu1 O7 2.363(5) . ?
N1 O5 1.351(5) . ?
N2 O6 1.361(5) . ?
O3 Cu1 1.929(4) 1_455 ?
O5 Cu1 1.974(3) 4_565 ?
O6 Cu1 1.973(3) 4_565 ?
O7 H7A 0.8552 . ?
O7 H7B 0.8569 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.6(4) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 C11 119.9(4) . . ?
C5 C4 C11 121.6(4) . . ?
N1 C5 C4 119.1(4) . . ?
N1 C5 C6 116.5(4) . . ?
C4 C5 C6 124.4(4) . . ?
N2 C6 C7 120.2(4) . . ?
N2 C6 C5 114.5(4) . . ?
C7 C6 C5 125.3(4) . . ?
C8 C7 C6 117.8(4) . . ?
C8 C7 C12 120.3(4) . . ?
C6 C7 C12 121.9(4) . . ?
C7 C8 C9 120.1(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N2 C10 C9 118.9(4) . . ?
N2 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
O2 C11 O1 126.2(5) . . ?
O2 C11 C4 116.8(5) . . ?
O1 C11 C4 117.0(4) . . ?
O4 C12 O3 127.4(4) . . ?
O4 C12 C7 118.2(4) . . ?
O3 C12 C7 114.3(4) . . ?
O3 Cu1 O6 90.86(15) 1_655 4_666 ?
O3 Cu1 O5 158.55(16) 1_655 4_666 ?
O6 Cu1 O5 90.57(15) 4_666 4_666 ?
O3 Cu1 O1 88.75(15) 1_655 . ?
O6 Cu1 O1 177.36(15) 4_666 . ?
O5 Cu1 O1 90.75(15) 4_666 . ?
O3 Cu1 O7 108.09(18) 1_655 . ?
O6 Cu1 O7 87.17(16) 4_666 . ?
O5 Cu1 O7 93.36(17) 4_666 . ?
O1 Cu1 O7 90.47(15) . . ?
C1 N1 C5 122.6(4) . . ?
C1 N1 O5 119.8(4) . . ?
C5 N1 O5 117.7(4) . . ?
C6 N2 C10 122.6(4) . . ?
C6 N2 O6 117.9(4) . . ?
C10 N2 O6 119.4(4) . . ?
C11 O1 Cu1 127.0(3) . . ?
C12 O3 Cu1 122.2(3) . 1_455 ?
N1 O5 Cu1 112.1(2) . 4_565 ?
N2 O6 Cu1 111.7(3) . 4_565 ?
Cu1 O7 H7A 141.8 . . ?
Cu1 O7 H7B 77.0 . . ?
H7A O7 H7B 114.8 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.142
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.359
_database_code_depnum_ccdc_archive 'CCDC 1018473'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H28 Cu2 N8 O12'
_chemical_formula_weight         1035.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   9.3276(10)
_cell_length_b                   11.9664(13)
_cell_length_c                   19.099(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.947(2)
_cell_angle_gamma                90.00
_cell_volume                     2128.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1547
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.25

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1052
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7380
_exptl_absorpt_correction_T_max  0.7743
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10555
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3790
_reflns_number_gt                2710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0428P)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         3790
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_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 0.7707(3) 0.6842(3) 0.79746(17) 0.0385(8) Uani 1 1 d . . .
H1 H 0.7522 0.7477 0.7704 0.046 Uiso 1 1 calc R . .
C2 C 0.6691(3) 0.6449(3) 0.83904(18) 0.0418(9) Uani 1 1 d . . .
H2 H 0.5814 0.6815 0.8406 0.050 Uiso 1 1 calc R . .
C3 C 0.6950(3) 0.5509(3) 0.87906(17) 0.0375(8) Uani 1 1 d . . .
H3 H 0.6266 0.5256 0.9090 0.045 Uiso 1 1 calc R . .
C4 C 0.8236(3) 0.4942(2) 0.87459(15) 0.0290(7) Uani 1 1 d . . .
C5 C 0.9265(3) 0.5359(2) 0.83176(15) 0.0267(7) Uani 1 1 d . . .
C6 C 1.0668(3) 0.4830(2) 0.81967(15) 0.0278(7) Uani 1 1 d . . .
C7 C 1.2001(3) 0.5250(2) 0.84211(16) 0.0299(7) Uani 1 1 d . . .
C8 C 1.3233(4) 0.4689(3) 0.82386(19) 0.0477(9) Uani 1 1 d . . .
H8 H 1.4134 0.4956 0.8388 0.057 Uiso 1 1 calc R . .
C9 C 1.3114(4) 0.3739(3) 0.7838(2) 0.0517(10) Uani 1 1 d . . .
H9 H 1.3934 0.3352 0.7722 0.062 Uiso 1 1 calc R . .
C10 C 1.1797(4) 0.3366(3) 0.76106(18) 0.0450(9) Uani 1 1 d . . .
H10 H 1.1726 0.2727 0.7333 0.054 Uiso 1 1 calc R . .
C11 C 0.8501(4) 0.3899(3) 0.91668(17) 0.0340(8) Uani 1 1 d . . .
C12 C 1.2147(4) 0.6276(3) 0.88735(17) 0.0328(8) Uani 1 1 d . . .
C13 C 0.6071(4) 0.1243(3) 0.90457(18) 0.0432(9) Uani 1 1 d . . .
H13 H 0.5923 0.1938 0.8836 0.052 Uiso 1 1 calc R . .
C14 C 0.5290(4) 0.0334(3) 0.87873(18) 0.0475(10) Uani 1 1 d . . .
H14 H 0.4631 0.0427 0.8410 0.057 Uiso 1 1 calc R . .
C15 C 0.5481(4) -0.0695(3) 0.90812(19) 0.0476(10) Uani 1 1 d . . .
H15 H 0.4950 -0.1302 0.8910 0.057 Uiso 1 1 calc R . .
C16 C 0.6493(4) -0.0829(3) 0.96477(18) 0.0385(8) Uani 1 1 d . . .
C17 C 0.6807(4) -0.1862(3) 0.9999(2) 0.0496(10) Uani 1 1 d . . .
H17 H 0.6316 -0.2505 0.9855 0.060 Uiso 1 1 calc R . .
C18 C 0.7801(4) -0.1924(3) 1.0536(2) 0.0475(9) Uani 1 1 d . . .
H18 H 0.7977 -0.2607 1.0756 0.057 Uiso 1 1 calc R . .
C19 C 0.8588(3) -0.0965(3) 1.07746(18) 0.0389(8) Uani 1 1 d . . .
C20 C 0.8282(3) 0.0066(3) 1.04528(17) 0.0348(8) Uani 1 1 d . . .
C21 C 0.7244(3) 0.0128(3) 0.98771(16) 0.0336(8) Uani 1 1 d . . .
C22 C 0.9652(4) -0.0951(3) 1.13250(19) 0.0473(9) Uani 1 1 d . . .
H22 H 0.9906 -0.1610 1.1558 0.057 Uiso 1 1 calc R . .
C23 C 1.0311(4) 0.0026(3) 1.15163(19) 0.0514(10) Uani 1 1 d . . .
H23 H 1.1022 0.0034 1.1876 0.062 Uiso 1 1 calc R . .
C24 C 0.9915(4) 0.1016(3) 1.11712(19) 0.0473(9) Uani 1 1 d . . .
H24 H 1.0362 0.1679 1.1314 0.057 Uiso 1 1 calc R . .
Cu1 Cu 0.81295(4) 0.23581(3) 1.010589(19) 0.03320(15) Uani 1 1 d . . .
N1 N 0.8993(3) 0.6319(2) 0.79486(13) 0.0322(6) Uani 1 1 d . . .
N2 N 1.0588(3) 0.3900(2) 0.77784(14) 0.0360(7) Uani 1 1 d . . .
N3 N 0.8924(3) 0.1046(2) 1.06461(14) 0.0370(7) Uani 1 1 d . . .
N4 N 0.7028(3) 0.1153(2) 0.95854(13) 0.0355(7) Uani 1 1 d . . .
O1 O 0.7421(2) 0.35256(18) 0.94798(11) 0.0425(6) Uani 1 1 d . . .
O2 O 0.9678(3) 0.3446(2) 0.92049(12) 0.0511(7) Uani 1 1 d . . .
O3 O 1.1077(2) 0.65489(17) 0.92197(11) 0.0341(5) Uani 1 1 d . . .
O4 O 1.3310(2) 0.6782(2) 0.89065(12) 0.0477(6) Uani 1 1 d . . .
O5 O 0.9976(2) 0.67500(19) 0.75670(12) 0.0455(6) Uani 1 1 d . . .
O6 O 0.9352(3) 0.3532(2) 0.75444(13) 0.0575(7) 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
C1 C2 1.352(4) . ?
C1 N1 1.356(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 C11 1.499(4) . ?
C5 N1 1.365(4) . ?
C5 C6 1.482(4) . ?
C6 N2 1.370(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.391(4) . ?
C7 C12 1.504(4) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.358(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.350(4) . ?
C10 H10 0.9300 . ?
C11 O2 1.224(4) . ?
C11 O1 1.278(4) . ?
C12 O4 1.241(3) . ?
C12 O3 1.268(4) . ?
C13 N4 1.333(4) . ?
C13 C14 1.386(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(5) . ?
C15 H15 0.9300 . ?
C16 C21 1.401(4) . ?
C16 C17 1.430(5) . ?
C17 C18 1.349(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.424(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(4) . ?
C19 C22 1.408(5) . ?
C20 N3 1.359(4) . ?
C20 C21 1.429(4) . ?
C21 N4 1.358(4) . ?
C22 C23 1.362(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(5) . ?
C23 H23 0.9300 . ?
C24 N3 1.329(4) . ?
C24 H24 0.9300 . ?
Cu1 O1 1.933(2) . ?
Cu1 O3 1.954(2) 3_767 ?
Cu1 N3 2.000(3) . ?
Cu1 N4 2.005(3) . ?
N1 O5 1.306(3) . ?
N2 O6 1.292(3) . ?
O3 Cu1 1.954(2) 3_767 ?

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
C2 C1 N1 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
N1 C1 H1 119.7 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 C11 119.7(3) . . ?
C5 C4 C11 121.1(3) . . ?
N1 C5 C4 119.5(3) . . ?
N1 C5 C6 114.9(3) . . ?
C4 C5 C6 125.6(3) . . ?
N2 C6 C7 119.7(3) . . ?
N2 C6 C5 114.6(3) . . ?
C7 C6 C5 125.6(3) . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 C12 121.7(3) . . ?
C8 C7 C12 119.1(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 121.5(3) . . ?
N2 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
O2 C11 O1 123.0(3) . . ?
O2 C11 C4 121.6(3) . . ?
O1 C11 C4 115.4(3) . . ?
O4 C12 O3 123.9(3) . . ?
O4 C12 C7 118.7(3) . . ?
O3 C12 C7 117.3(3) . . ?
N4 C13 C14 122.0(3) . . ?
N4 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C21 C16 C15 116.8(3) . . ?
C21 C16 C17 118.2(3) . . ?
C15 C16 C17 125.0(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C22 115.9(3) . . ?
C20 C19 C18 118.7(3) . . ?
C22 C19 C18 125.4(3) . . ?
N3 C20 C19 124.3(3) . . ?
N3 C20 C21 115.9(3) . . ?
C19 C20 C21 119.8(3) . . ?
N4 C21 C16 123.3(3) . . ?
N4 C21 C20 116.3(3) . . ?
C16 C21 C20 120.5(3) . . ?
C23 C22 C19 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C19 C22 H22 120.0 . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N3 C24 C23 122.4(3) . . ?
N3 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
O1 Cu1 O3 91.72(9) . 3_767 ?
O1 Cu1 N3 172.85(10) . . ?
O3 Cu1 N3 93.88(10) 3_767 . ?
O1 Cu1 N4 93.61(10) . . ?
O3 Cu1 N4 167.25(10) 3_767 . ?
N3 Cu1 N4 81.83(11) . . ?
O5 N1 C1 119.1(3) . . ?
O5 N1 C5 120.2(2) . . ?
C1 N1 C5 120.7(3) . . ?
O6 N2 C10 119.9(3) . . ?
O6 N2 C6 120.0(3) . . ?
C10 N2 C6 120.1(3) . . ?
C24 N3 C20 117.5(3) . . ?
C24 N3 Cu1 129.4(2) . . ?
C20 N3 Cu1 113.0(2) . . ?
C13 N4 C21 118.0(3) . . ?
C13 N4 Cu1 129.1(2) . . ?
C21 N4 Cu1 112.6(2) . . ?
C11 O1 Cu1 106.8(2) . . ?
C12 O3 Cu1 103.53(18) . 3_767 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.2(5) . . . . ?
C1 C2 C3 C4 -2.5(5) . . . . ?
C2 C3 C4 C5 2.6(5) . . . . ?
C2 C3 C4 C11 -178.2(3) . . . . ?
C3 C4 C5 N1 0.0(4) . . . . ?
C11 C4 C5 N1 -179.2(3) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C11 C4 C5 C6 3.0(5) . . . . ?
N1 C5 C6 N2 -104.4(3) . . . . ?
C4 C5 C6 N2 73.6(4) . . . . ?
N1 C5 C6 C7 70.2(4) . . . . ?
C4 C5 C6 C7 -111.9(4) . . . . ?
N2 C6 C7 C8 -2.5(5) . . . . ?
C5 C6 C7 C8 -176.8(3) . . . . ?
N2 C6 C7 C12 179.2(3) . . . . ?
C5 C6 C7 C12 4.9(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C12 C7 C8 C9 178.7(3) . . . . ?
C7 C8 C9 C10 1.3(6) . . . . ?
C8 C9 C10 N2 -1.0(6) . . . . ?
C3 C4 C11 O2 -171.4(3) . . . . ?
C5 C4 C11 O2 7.7(5) . . . . ?
C3 C4 C11 O1 8.4(4) . . . . ?
C5 C4 C11 O1 -172.5(3) . . . . ?
C6 C7 C12 O4 -161.2(3) . . . . ?
C8 C7 C12 O4 20.6(5) . . . . ?
C6 C7 C12 O3 21.2(4) . . . . ?
C8 C7 C12 O3 -157.0(3) . . . . ?
N4 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C14 C15 C16 C21 0.3(5) . . . . ?
C14 C15 C16 C17 -179.4(3) . . . . ?
C21 C16 C17 C18 -0.2(5) . . . . ?
C15 C16 C17 C18 179.5(3) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 1.9(5) . . . . ?
C17 C18 C19 C22 -179.4(3) . . . . ?
C22 C19 C20 N3 -1.0(5) . . . . ?
C18 C19 C20 N3 177.9(3) . . . . ?
C22 C19 C20 C21 178.4(3) . . . . ?
C18 C19 C20 C21 -2.8(5) . . . . ?
C15 C16 C21 N4 0.6(5) . . . . ?
C17 C16 C21 N4 -179.6(3) . . . . ?
C15 C16 C21 C20 179.5(3) . . . . ?
C17 C16 C21 C20 -0.7(5) . . . . ?
N3 C20 C21 N4 0.6(4) . . . . ?
C19 C20 C21 N4 -178.8(3) . . . . ?
N3 C20 C21 C16 -178.4(3) . . . . ?
C19 C20 C21 C16 2.3(5) . . . . ?
C20 C19 C22 C23 0.2(5) . . . . ?
C18 C19 C22 C23 -178.5(3) . . . . ?
C19 C22 C23 C24 0.8(5) . . . . ?
C22 C23 C24 N3 -1.2(5) . . . . ?
C2 C1 N1 O5 -176.8(3) . . . . ?
C2 C1 N1 C5 2.9(5) . . . . ?
C4 C5 N1 O5 177.0(3) . . . . ?
C6 C5 N1 O5 -5.0(4) . . . . ?
C4 C5 N1 C1 -2.7(4) . . . . ?
C6 C5 N1 C1 175.4(3) . . . . ?
C9 C10 N2 O6 178.9(3) . . . . ?
C9 C10 N2 C6 -1.2(5) . . . . ?
C7 C6 N2 O6 -177.2(3) . . . . ?
C5 C6 N2 O6 -2.3(4) . . . . ?
C7 C6 N2 C10 2.9(4) . . . . ?
C5 C6 N2 C10 177.8(3) . . . . ?
C23 C24 N3 C20 0.5(5) . . . . ?
C23 C24 N3 Cu1 177.1(3) . . . . ?
C19 C20 N3 C24 0.6(5) . . . . ?
C21 C20 N3 C24 -178.7(3) . . . . ?
C19 C20 N3 Cu1 -176.5(3) . . . . ?
C21 C20 N3 Cu1 4.1(3) . . . . ?
O3 Cu1 N3 C24 -14.0(3) 3_767 . . . ?
N4 Cu1 N3 C24 178.0(3) . . . . ?
O3 Cu1 N3 C20 162.7(2) 3_767 . . . ?
N4 Cu1 N3 C20 -5.3(2) . . . . ?
C14 C13 N4 C21 1.0(5) . . . . ?
C14 C13 N4 Cu1 -173.3(3) . . . . ?
C16 C21 N4 C13 -1.3(5) . . . . ?
C20 C21 N4 C13 179.8(3) . . . . ?
C16 C21 N4 Cu1 173.9(2) . . . . ?
C20 C21 N4 Cu1 -5.0(3) . . . . ?
O1 Cu1 N4 C13 -5.4(3) . . . . ?
O3 Cu1 N4 C13 109.1(5) 3_767 . . . ?
N3 Cu1 N4 C13 -179.9(3) . . . . ?
O1 Cu1 N4 C21 -180.0(2) . . . . ?
O3 Cu1 N4 C21 -65.5(5) 3_767 . . . ?
N3 Cu1 N4 C21 5.6(2) . . . . ?
O2 C11 O1 Cu1 9.7(4) . . . . ?
C4 C11 O1 Cu1 -170.0(2) . . . . ?
O3 Cu1 O1 C11 77.0(2) 3_767 . . . ?
N4 Cu1 O1 C11 -114.6(2) . . . . ?
O4 C12 O3 Cu1 -11.5(4) . . . 3_767 ?
C7 C12 O3 Cu1 165.9(2) . . . 3_767 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1018474'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H48 Cu2 N8 O22'
_chemical_formula_weight         1216.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   9.213(2)
_cell_length_b                   12.190(3)
_cell_length_c                   12.635(3)
_cell_angle_alpha                109.362(4)
_cell_angle_beta                 109.077(4)
_cell_angle_gamma                91.212(4)
_cell_volume                     1251.8(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3505
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             626
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7983
_exptl_absorpt_correction_T_max  0.8637
_exptl_absorpt_process_details   'Bruker 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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6190
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4345
_reflns_number_gt                3779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0950P)²+1.7921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4345
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.3937(4) 0.0995(3) 0.0758(3) 0.0257(7) Uani 1 1 d . . .
C2 C 0.2449(4) 0.0336(3) -0.0238(3) 0.0235(7) Uani 1 1 d . . .
C3 C 0.1690(4) -0.0670(3) -0.0244(3) 0.0308(8) Uani 1 1 d . . .
H3 H 0.2129 -0.0986 0.0345 0.037 Uiso 1 1 calc R . .
C4 C 0.0275(5) -0.1186(3) -0.1139(4) 0.0360(9) Uani 1 1 d . . .
H4 H -0.0249 -0.1856 -0.1157 0.043 Uiso 1 1 calc R . .
C5 C -0.0355(4) -0.0717(3) -0.1997(4) 0.0360(9) Uani 1 1 d . . .
H5 H -0.1317 -0.1067 -0.2588 0.043 Uiso 1 1 calc R . .
C6 C 0.1794(4) 0.0754(3) -0.1158(3) 0.0230(7) Uani 1 1 d . . .
C7 C 0.2505(4) 0.1797(3) -0.1259(3) 0.0245(7) Uani 1 1 d . . .
C8 C 0.2741(5) 0.3886(3) -0.0625(4) 0.0361(9) Uani 1 1 d . . .
H8 H 0.2473 0.4590 -0.0212 0.043 Uiso 1 1 calc R . .
C9 C 0.3700(5) 0.3885(3) -0.1257(4) 0.0364(9) Uani 1 1 d . . .
H9 H 0.4091 0.4593 -0.1261 0.044 Uiso 1 1 calc R . .
C10 C 0.4091(5) 0.2853(3) -0.1884(4) 0.0337(8) Uani 1 1 d . . .
H10 H 0.4760 0.2859 -0.2297 0.040 Uiso 1 1 calc R . .
C11 C 0.3473(4) 0.1796(3) -0.1892(3) 0.0264(7) Uani 1 1 d . . .
C12 C 0.3901(4) 0.0658(3) -0.2578(3) 0.0311(8) Uani 1 1 d . . .
C13 C 0.9048(5) 0.2161(4) 0.4997(4) 0.0407(9) Uani 1 1 d . . .
H13 H 0.9044 0.1353 0.4712 0.049 Uiso 1 1 calc R . .
C14 C 1.0273(5) 0.2868(4) 0.6041(4) 0.0511(11) Uani 1 1 d . . .
H14 H 1.1067 0.2528 0.6434 0.061 Uiso 1 1 calc R . .
C15 C 1.0286(6) 0.4050(4) 0.6467(4) 0.0496(11) Uani 1 1 d . . .
H15 H 1.1081 0.4522 0.7161 0.059 Uiso 1 1 calc R . .
C16 C 0.9103(5) 0.4552(4) 0.5861(4) 0.0388(9) Uani 1 1 d . . .
C17 C 0.9002(6) 0.5802(4) 0.6211(4) 0.0521(12) Uani 1 1 d . . .
H17 H 0.9782 0.6325 0.6881 0.063 Uiso 1 1 calc R . .
C18 C 0.7814(7) 0.6219(4) 0.5595(4) 0.0520(12) Uani 1 1 d . . .
H18 H 0.7791 0.7025 0.5840 0.062 Uiso 1 1 calc R . .
C19 C 0.6583(6) 0.5448(3) 0.4567(4) 0.0398(10) Uani 1 1 d . . .
C20 C 0.6636(4) 0.4235(3) 0.4204(3) 0.0291(8) Uani 1 1 d . . .
C21 C 0.7927(4) 0.3787(3) 0.4844(3) 0.0296(8) Uani 1 1 d . . .
C22 C 0.5288(6) 0.5815(4) 0.3893(4) 0.0479(11) Uani 1 1 d . . .
H22 H 0.5198 0.6611 0.4098 0.057 Uiso 1 1 calc R . .
C23 C 0.4159(6) 0.5009(4) 0.2936(4) 0.0462(11) Uani 1 1 d . . .
H23 H 0.3305 0.5250 0.2478 0.055 Uiso 1 1 calc R . .
C24 C 0.4297(5) 0.3808(4) 0.2648(4) 0.0381(9) Uani 1 1 d . . .
H24 H 0.3516 0.3262 0.2001 0.046 Uiso 1 1 calc R . .
Cu1 Cu 0.59513(5) 0.17674(3) 0.30437(4) 0.02532(18) Uani 1 1 d . . .
N1 N 0.0383(3) 0.0245(3) -0.2010(3) 0.0292(7) Uani 1 1 d . . .
N2 N 0.2178(4) 0.2850(3) -0.0603(3) 0.0294(7) Uani 1 1 d . . .
N3 N 0.5495(4) 0.3432(3) 0.3263(3) 0.0292(7) Uani 1 1 d . . .
N4 N 0.7913(4) 0.2611(3) 0.4416(3) 0.0304(7) Uani 1 1 d . . .
O1 O 0.3973(3) 0.1038(2) 0.1795(2) 0.0318(6) Uani 1 1 d . . .
O2 O 0.4955(3) 0.1454(2) 0.0558(2) 0.0346(6) Uani 1 1 d . . .
O3 O -0.0219(3) 0.0685(3) -0.2847(3) 0.0458(7) Uani 1 1 d . . .
O4 O 0.3209(3) -0.0279(2) -0.2673(2) 0.0305(6) Uani 1 1 d . . .
O5 O 0.4934(4) 0.0745(3) -0.2998(4) 0.0585(10) Uani 1 1 d . . .
O6 O 0.1338(4) 0.2854(2) 0.0050(3) 0.0418(7) Uani 1 1 d . . .
O1W O 0.5007(4) 0.1418(3) 0.4513(3) 0.0552(9) Uani 1 1 d . . .
O2W O 0.7195(5) 0.3505(3) 0.1307(4) 0.0677(10) Uani 1 1 d . . .
O3W O 0.7340(4) 0.2025(3) 0.6978(4) 0.0643(10) Uani 1 1 d . . .
O4W O 0.8446(5) 0.3587(4) 0.9494(4) 0.0819(13) Uani 1 1 d . . .
O5W O 0.7870(8) 0.9046(6) 0.4997(5) 0.136(2) Uani 1 1 d . . .
H1A H 0.4847 0.0687 0.4077 0.205 Uiso 1 1 d R . .
H1B H 0.5672 0.1582 0.5219 0.205 Uiso 1 1 d R . .
H2A H 0.6543 0.2891 0.1085 0.205 Uiso 1 1 d R . .
H2B H 0.7572 0.3517 0.0774 0.205 Uiso 1 1 d R . .
H3A H 0.8092 0.1612 0.7039 0.205 Uiso 1 1 d R . .
H3B H 0.6593 0.1618 0.6995 0.205 Uiso 1 1 d R . .
H4A H 0.9348 0.3351 0.9674 0.205 Uiso 1 1 d R . .
H4B H 0.8137 0.3120 0.8773 0.205 Uiso 1 1 d R . .
H5A H 0.8458 0.9550 0.5662 0.205 Uiso 1 1 d R . .
H5B H 0.7055 0.8916 0.5138 0.205 Uiso 1 1 d R . .


_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 1.218(4) . ?
C1 O1 1.282(5) . ?
C1 C2 1.505(5) . ?
C2 C6 1.387(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.350(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.357(4) . ?
C6 C7 1.480(5) . ?
C7 C11 1.378(5) . ?
C7 N2 1.378(5) . ?
C8 N2 1.368(5) . ?
C8 C9 1.371(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.510(5) . ?
C12 O4 1.246(4) . ?
C12 O5 1.249(5) . ?
C13 N4 1.312(5) . ?
C13 C14 1.410(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(7) . ?
C15 H15 0.9300 . ?
C16 C21 1.396(5) . ?
C16 C17 1.453(6) . ?
C17 C18 1.338(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.428(7) . ?
C18 H18 0.9300 . ?
C19 C22 1.400(7) . ?
C19 C20 1.402(5) . ?
C20 N3 1.358(5) . ?
C20 C21 1.435(5) . ?
C21 N4 1.352(5) . ?
C22 C23 1.362(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.405(6) . ?
C23 H23 0.9300 . ?
C24 N3 1.315(5) . ?
C24 H24 0.9300 . ?
Cu1 O1 1.929(3) . ?
Cu1 O4 1.961(2) 2_655 ?
Cu1 N4 2.005(3) . ?
Cu1 N3 2.027(3) . ?
Cu1 O1W 2.439(3) . ?
N1 O3 1.312(4) . ?
N2 O6 1.302(4) . ?
O4 Cu1 1.960(2) 2_655 ?
O1W H1A 0.8576 . ?
O1W H1B 0.8552 . ?
O2W H2A 0.8545 . ?
O2W H2B 0.8570 . ?
O3W H3A 0.8636 . ?
O3W H3B 0.8509 . ?
O4W H4A 0.8691 . ?
O4W H4B 0.8454 . ?
O5W H5A 0.8500 . ?
O5W H5B 0.8500 . ?

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 125.6(3) . . ?
O2 C1 C2 121.1(3) . . ?
O1 C1 C2 113.3(3) . . ?
C6 C2 C3 119.1(3) . . ?
C6 C2 C1 119.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N1 C6 C2 120.7(3) . . ?
N1 C6 C7 115.2(3) . . ?
C2 C6 C7 124.0(3) . . ?
C11 C7 N2 119.6(3) . . ?
C11 C7 C6 126.3(3) . . ?
N2 C7 C6 114.1(3) . . ?
N2 C8 C9 119.9(3) . . ?
N2 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C7 C11 C10 120.0(3) . . ?
C7 C11 C12 120.6(3) . . ?
C10 C11 C12 119.3(3) . . ?
O4 C12 O5 125.7(3) . . ?
O4 C12 C11 117.9(3) . . ?
O5 C12 C11 116.4(3) . . ?
N4 C13 C14 122.0(4) . . ?
N4 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 119.5(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C21 116.9(4) . . ?
C15 C16 C17 125.1(4) . . ?
C21 C16 C17 118.0(4) . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C22 C19 C20 116.7(4) . . ?
C22 C19 C18 124.4(4) . . ?
C20 C19 C18 118.8(4) . . ?
N3 C20 C19 123.0(4) . . ?
N3 C20 C21 116.7(3) . . ?
C19 C20 C21 120.2(4) . . ?
N4 C21 C16 123.4(4) . . ?
N4 C21 C20 116.5(3) . . ?
C16 C21 C20 120.0(3) . . ?
C23 C22 C19 120.1(4) . . ?
C23 C22 H22 120.0 . . ?
C19 C22 H22 120.0 . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N3 C24 C23 122.2(4) . . ?
N3 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
O1 Cu1 O4 91.21(11) . 2_655 ?
O1 Cu1 N4 175.37(12) . . ?
O4 Cu1 N4 92.71(12) 2_655 . ?
O1 Cu1 N3 94.60(12) . . ?
O4 Cu1 N3 165.02(12) 2_655 . ?
N4 Cu1 N3 82.20(13) . . ?
O1 Cu1 O1W 90.19(12) . . ?
O4 Cu1 O1W 94.16(11) 2_655 . ?
N4 Cu1 O1W 87.06(13) . . ?
N3 Cu1 O1W 99.61(12) . . ?
O3 N1 C5 121.4(3) . . ?
O3 N1 C6 119.0(3) . . ?
C5 N1 C6 119.7(3) . . ?
O6 N2 C8 120.0(3) . . ?
O6 N2 C7 119.6(3) . . ?
C8 N2 C7 120.5(3) . . ?
C24 N3 C20 118.6(3) . . ?
C24 N3 Cu1 129.8(3) . . ?
C20 N3 Cu1 111.7(2) . . ?
C13 N4 C21 118.4(3) . . ?
C13 N4 Cu1 128.5(3) . . ?
C21 N4 Cu1 112.7(2) . . ?
C1 O1 Cu1 112.9(2) . . ?
C12 O4 Cu1 122.5(2) . 2_655 ?
Cu1 O1W H1A 86.5 . . ?
Cu1 O1W H1B 116.6 . . ?
H1A O1W H1B 113.7 . . ?
H2A O2W H2B 113.4 . . ?
H3A O3W H3B 105.4 . . ?
H4A O4W H4B 93.7 . . ?
H5A O5W H5B 102.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C6 -37.5(5) . . . . ?
O1 C1 C2 C6 140.7(3) . . . . ?
O2 C1 C2 C3 144.1(4) . . . . ?
O1 C1 C2 C3 -37.7(4) . . . . ?
C6 C2 C3 C4 -2.8(5) . . . . ?
C1 C2 C3 C4 175.6(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 N1 1.0(6) . . . . ?
C3 C2 C6 N1 4.5(5) . . . . ?
C1 C2 C6 N1 -173.9(3) . . . . ?
C3 C2 C6 C7 -178.8(3) . . . . ?
C1 C2 C6 C7 2.8(5) . . . . ?
N1 C6 C7 C11 -90.2(4) . . . . ?
C2 C6 C7 C11 92.9(4) . . . . ?
N1 C6 C7 N2 92.5(4) . . . . ?
C2 C6 C7 N2 -84.4(4) . . . . ?
N2 C8 C9 C10 0.8(6) . . . . ?
C8 C9 C10 C11 1.3(6) . . . . ?
N2 C7 C11 C10 -1.2(5) . . . . ?
C6 C7 C11 C10 -178.4(3) . . . . ?
N2 C7 C11 C12 177.6(3) . . . . ?
C6 C7 C11 C12 0.4(5) . . . . ?
C9 C10 C11 C7 -1.1(5) . . . . ?
C9 C10 C11 C12 -179.9(3) . . . . ?
C7 C11 C12 O4 8.5(5) . . . . ?
C10 C11 C12 O4 -172.7(3) . . . . ?
C7 C11 C12 O5 -171.1(4) . . . . ?
C10 C11 C12 O5 7.7(5) . . . . ?
N4 C13 C14 C15 0.3(7) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
C14 C15 C16 C21 1.6(7) . . . . ?
C14 C15 C16 C17 -178.7(5) . . . . ?
C15 C16 C17 C18 -178.8(5) . . . . ?
C21 C16 C17 C18 0.8(7) . . . . ?
C16 C17 C18 C19 0.6(7) . . . . ?
C17 C18 C19 C22 178.6(5) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C22 C19 C20 N3 -1.1(6) . . . . ?
C18 C19 C20 N3 177.8(4) . . . . ?
C22 C19 C20 C21 179.7(4) . . . . ?
C18 C19 C20 C21 -1.4(6) . . . . ?
C15 C16 C21 N4 -1.8(6) . . . . ?
C17 C16 C21 N4 178.5(4) . . . . ?
C15 C16 C21 C20 177.2(4) . . . . ?
C17 C16 C21 C20 -2.4(6) . . . . ?
N3 C20 C21 N4 2.7(5) . . . . ?
C19 C20 C21 N4 -178.1(3) . . . . ?
N3 C20 C21 C16 -176.5(3) . . . . ?
C19 C20 C21 C16 2.8(5) . . . . ?
C20 C19 C22 C23 -0.1(6) . . . . ?
C18 C19 C22 C23 -178.9(4) . . . . ?
C19 C22 C23 C24 1.0(6) . . . . ?
C22 C23 C24 N3 -0.9(6) . . . . ?
C4 C5 N1 O3 179.1(4) . . . . ?
C4 C5 N1 C6 0.7(5) . . . . ?
C2 C6 N1 O3 178.1(3) . . . . ?
C7 C6 N1 O3 1.1(4) . . . . ?
C2 C6 N1 C5 -3.5(5) . . . . ?
C7 C6 N1 C5 179.6(3) . . . . ?
C9 C8 N2 O6 176.2(4) . . . . ?
C9 C8 N2 C7 -3.3(5) . . . . ?
C11 C7 N2 O6 -176.0(3) . . . . ?
C6 C7 N2 O6 1.5(5) . . . . ?
C11 C7 N2 C8 3.4(5) . . . . ?
C6 C7 N2 C8 -179.1(3) . . . . ?
C23 C24 N3 C20 -0.3(6) . . . . ?
C23 C24 N3 Cu1 179.3(3) . . . . ?
C19 C20 N3 C24 1.4(5) . . . . ?
C21 C20 N3 C24 -179.4(3) . . . . ?
C19 C20 N3 Cu1 -178.3(3) . . . . ?
C21 C20 N3 Cu1 0.9(4) . . . . ?
O1 Cu1 N3 C24 -5.7(3) . . . . ?
O4 Cu1 N3 C24 106.8(5) 2_655 . . . ?
N4 Cu1 N3 C24 177.7(4) . . . . ?
O1W Cu1 N3 C24 -96.7(3) . . . . ?
O1 Cu1 N3 C20 173.9(2) . . . . ?
O4 Cu1 N3 C20 -73.6(5) 2_655 . . . ?
N4 Cu1 N3 C20 -2.7(2) . . . . ?
O1W Cu1 N3 C20 83.0(3) . . . . ?
C14 C13 N4 C21 -0.4(6) . . . . ?
C14 C13 N4 Cu1 -172.2(3) . . . . ?
C16 C21 N4 C13 1.2(6) . . . . ?
C20 C21 N4 C13 -177.9(3) . . . . ?
C16 C21 N4 Cu1 174.2(3) . . . . ?
C20 C21 N4 Cu1 -4.9(4) . . . . ?
O1 Cu1 N4 C13 129.8(13) . . . . ?
O4 Cu1 N4 C13 -17.9(4) 2_655 . . . ?
N3 Cu1 N4 C13 176.3(4) . . . . ?
O1W Cu1 N4 C13 76.1(4) . . . . ?
O1 Cu1 N4 C21 -42.3(15) . . . . ?
O4 Cu1 N4 C21 170.0(3) 2_655 . . . ?
N3 Cu1 N4 C21 4.1(2) . . . . ?
O1W Cu1 N4 C21 -96.0(3) . . . . ?
O2 C1 O1 Cu1 -6.9(5) . . . . ?
C2 C1 O1 Cu1 175.0(2) . . . . ?
O4 Cu1 O1 C1 -84.3(2) 2_655 . . . ?
N4 Cu1 O1 C1 128.0(14) . . . . ?
N3 Cu1 O1 C1 81.9(2) . . . . ?
O1W Cu1 O1 C1 -178.4(2) . . . . ?
O5 C12 O4 Cu1 20.3(6) . . . 2_655 ?
C11 C12 O4 Cu1 -159.3(2) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 1018475'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H40 Cu2 N8 O18'
_chemical_formula_weight         1095.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   9.357(4)
_cell_length_b                   11.325(5)
_cell_length_c                   12.540(5)
_cell_angle_alpha                64.338(6)
_cell_angle_beta                 69.757(6)
_cell_angle_gamma                75.003(6)
_cell_volume                     1114.4(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2108
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.16

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             562
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8344
_exptl_absorpt_correction_T_max  0.8508
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5612
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3875
_reflns_number_gt                3204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1943P)²+0.2799P] 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         3875
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.2373
_refine_ls_wR_factor_gt          0.1643
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.61539(6) 0.82624(5) 0.31723(5) 0.0222(3) Uani 1 1 d . . .
O1 O 0.7466(4) 0.6602(3) 0.3718(3) 0.0281(8) Uani 1 1 d . . .
O1W O 0.7667(5) 0.9436(5) 0.3518(4) 0.0449(11) Uani 1 1 d . . .
O2 O 0.5919(5) 0.5797(4) 0.3287(5) 0.0466(12) Uani 1 1 d . . .
O3 O 0.5244(4) 0.2158(4) 0.5169(3) 0.0269(8) Uani 1 1 d . . .
O4 O 0.3545(5) 0.2331(5) 0.4217(4) 0.0395(10) Uani 1 1 d . . .
O5 O 0.8802(4) 0.1183(4) 0.4005(4) 0.0304(9) Uani 1 1 d . . .
O6 O 0.9564(5) 0.4346(6) 0.1672(4) 0.0539(14) Uani 1 1 d . . .
N1 N 0.8669(4) 0.2119(4) 0.4401(4) 0.0197(9) Uani 1 1 d . . .
N2 N 0.8268(5) 0.4004(4) 0.1778(4) 0.0254(10) Uani 1 1 d . . .
N3 N 0.7384(5) 0.8795(4) 0.1392(4) 0.0260(10) Uani 1 1 d . . .
N4 N 0.4769(5) 0.9862(4) 0.2428(4) 0.0240(9) Uani 1 1 d . . .
C1 C 0.6954(6) 0.5665(5) 0.3723(5) 0.0249(11) Uani 1 1 d . . .
C2 C 0.7782(5) 0.4317(5) 0.4296(4) 0.0206(10) Uani 1 1 d . . .
C3 C 0.8479(6) 0.4086(5) 0.5184(5) 0.0272(11) Uani 1 1 d . . .
H3 H 0.8419 0.4752 0.5449 0.033 Uiso 1 1 calc R . .
C4 C 0.9276(7) 0.2839(5) 0.5687(5) 0.0303(12) Uani 1 1 d . . .
H4 H 0.9750 0.2668 0.6289 0.036 Uiso 1 1 calc R . .
C5 C 0.9350(6) 0.1888(5) 0.5287(5) 0.0283(12) Uani 1 1 d . . .
H5 H 0.9877 0.1058 0.5623 0.034 Uiso 1 1 calc R . .
C6 C 0.7865(5) 0.3313(5) 0.3924(4) 0.0180(10) Uani 1 1 d . . .
C7 C 0.7299(5) 0.3465(5) 0.2894(4) 0.0188(10) Uani 1 1 d . . .
C8 C 0.7931(7) 0.4216(6) 0.0731(5) 0.0342(13) Uani 1 1 d . . .
H8 H 0.8601 0.4609 -0.0030 0.041 Uiso 1 1 calc R . .
C9 C 0.6608(6) 0.3851(6) 0.0798(5) 0.0303(12) Uani 1 1 d . . .
H9 H 0.6388 0.3980 0.0083 0.036 Uiso 1 1 calc R . .
C10 C 0.5599(6) 0.3291(6) 0.1929(5) 0.0301(12) Uani 1 1 d . . .
H10 H 0.4698 0.3045 0.1978 0.036 Uiso 1 1 calc R . .
C11 C 0.5930(6) 0.3099(5) 0.2983(5) 0.0210(10) Uani 1 1 d . . .
C12 C 0.4795(6) 0.2484(5) 0.4225(5) 0.0247(11) Uani 1 1 d . . .
C13 C 0.8753(7) 0.8169(6) 0.0944(6) 0.0362(13) Uani 1 1 d . . .
H13 H 0.9137 0.7367 0.1470 0.043 Uiso 1 1 calc R . .
C14 C 0.9589(7) 0.8674(7) -0.0252(6) 0.0407(15) Uani 1 1 d . . .
H14 H 1.0517 0.8217 -0.0541 0.049 Uiso 1 1 calc R . .
C15 C 0.9030(7) 0.9872(7) -0.1019(5) 0.0404(15) Uani 1 1 d . . .
H15 H 0.9589 1.0243 -0.1833 0.048 Uiso 1 1 calc R . .
C16 C 0.7648(6) 1.0519(5) -0.0582(5) 0.0293(12) Uani 1 1 d . . .
H16 H 0.7260 1.1331 -0.1092 0.035 Uiso 1 1 calc R . .
C17 C 0.6837(6) 0.9940(5) 0.0638(5) 0.0241(11) Uani 1 1 d . . .
C18 C 0.5303(6) 1.0510(5) 0.1226(5) 0.0234(11) Uani 1 1 d . . .
C19 C 0.4481(6) 1.1621(5) 0.0571(5) 0.0285(12) Uani 1 1 d . . .
H19 H 0.4879 1.2074 -0.0266 0.034 Uiso 1 1 calc R . .
C20 C 0.3027(6) 1.2052(6) 0.1201(6) 0.0341(13) Uani 1 1 d . . .
H20 H 0.2443 1.2802 0.0785 0.041 Uiso 1 1 calc R . .
C21 C 0.2471(7) 1.1365(6) 0.2428(6) 0.0365(13) Uani 1 1 d . . .
H21 H 0.1497 1.1630 0.2853 0.044 Uiso 1 1 calc R . .
C22 C 0.3376(6) 1.0269(5) 0.3032(5) 0.0280(11) Uani 1 1 d . . .
H22 H 0.3010 0.9807 0.3871 0.034 Uiso 1 1 calc R . .
O2W O 0.3712(6) 0.6396(5) 0.1967(4) 0.0583(13) Uani 1 1 d . . .
O3W O 0.1774(6) 0.4495(5) 0.2653(5) 0.0617(14) Uani 1 1 d . . .
H2A H 0.4360 0.6216 0.2376 0.093 Uiso 1 1 d R . .
H2B H 0.3121 0.5820 0.2186 0.093 Uiso 1 1 d R . .
H3A H 0.1105 0.4451 0.2359 0.093 Uiso 1 1 d R . .
H3B H 0.2287 0.3868 0.3109 0.093 Uiso 1 1 d R . .
H1WA H 0.7544 0.9276 0.4282 0.093 Uiso 1 1 d R . .
H1WB H 0.8128 1.0121 0.3201 0.093 Uiso 1 1 d R . .


_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 O1 1.945(4) . ?
Cu1 O3 1.961(4) 2_666 ?
Cu1 N4 1.997(4) . ?
Cu1 N3 2.022(4) . ?
Cu1 O1W 2.420(4) . ?
O1 C1 1.269(6) . ?
O1W H1WA 0.8644 . ?
O1W H1WB 0.8568 . ?
O2 C1 1.217(6) . ?
O3 C12 1.264(6) . ?
O3 Cu1 1.961(4) 2_666 ?
O4 C12 1.230(6) . ?
O5 N1 1.317(5) . ?
O6 N2 1.314(6) . ?
N1 C6 1.355(6) . ?
N1 C5 1.365(7) . ?
N2 C7 1.350(6) . ?
N2 C8 1.362(7) . ?
N3 C17 1.329(7) . ?
N3 C13 1.355(7) . ?
N4 C18 1.331(7) . ?
N4 C22 1.340(7) . ?
C1 C2 1.506(7) . ?
C2 C3 1.377(7) . ?
C2 C6 1.380(7) . ?
C3 C4 1.399(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.349(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.487(6) . ?
C7 C11 1.401(7) . ?
C8 C9 1.369(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.529(7) . ?
C13 C14 1.366(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.490(7) . ?
C18 C19 1.375(7) . ?
C19 C20 1.400(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
O2W H2A 0.8570 . ?
O2W H2B 0.8557 . ?
O3W H3A 0.8501 . ?
O3W H3B 0.8500 . ?

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
O1 Cu1 O3 90.94(16) . 2_666 ?
O1 Cu1 N4 170.91(16) . . ?
O3 Cu1 N4 93.65(16) 2_666 . ?
O1 Cu1 N3 94.34(17) . . ?
O3 Cu1 N3 173.58(15) 2_666 . ?
N4 Cu1 N3 80.63(17) . . ?
O1 Cu1 O1W 92.06(16) . . ?
O3 Cu1 O1W 93.31(15) 2_666 . ?
N4 Cu1 O1W 95.50(17) . . ?
N3 Cu1 O1W 90.15(16) . . ?
C1 O1 Cu1 110.8(3) . . ?
Cu1 O1W H1WA 114.7 . . ?
Cu1 O1W H1WB 144.6 . . ?
H1WA O1W H1WB 97.9 . . ?
C12 O3 Cu1 123.0(3) . 2_666 ?
O5 N1 C6 120.0(4) . . ?
O5 N1 C5 119.9(4) . . ?
C6 N1 C5 120.1(4) . . ?
O6 N2 C7 120.7(4) . . ?
O6 N2 C8 118.1(4) . . ?
C7 N2 C8 121.2(4) . . ?
C17 N3 C13 118.7(5) . . ?
C17 N3 Cu1 114.8(3) . . ?
C13 N3 Cu1 126.1(4) . . ?
C18 N4 C22 120.0(4) . . ?
C18 N4 Cu1 114.8(3) . . ?
C22 N4 Cu1 125.1(4) . . ?
O2 C1 O1 125.1(5) . . ?
O2 C1 C2 120.8(4) . . ?
O1 C1 C2 114.0(4) . . ?
C3 C2 C6 119.6(5) . . ?
C3 C2 C1 120.0(4) . . ?
C6 C2 C1 120.4(4) . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 N1 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
N1 C5 H5 119.3 . . ?
N1 C6 C2 120.2(4) . . ?
N1 C6 C7 114.3(4) . . ?
C2 C6 C7 125.0(4) . . ?
N2 C7 C11 119.6(4) . . ?
N2 C7 C6 113.3(4) . . ?
C11 C7 C6 127.1(4) . . ?
N2 C8 C9 120.1(5) . . ?
N2 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.8(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C7 119.3(5) . . ?
C10 C11 C12 119.1(4) . . ?
C7 C11 C12 121.6(4) . . ?
O4 C12 O3 126.0(5) . . ?
O4 C12 C11 117.4(4) . . ?
O3 C12 C11 116.6(4) . . ?
N3 C13 C14 122.3(6) . . ?
N3 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 118.6(5) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 118.8(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
N3 C17 C16 121.7(5) . . ?
N3 C17 C18 113.7(4) . . ?
C16 C17 C18 124.6(5) . . ?
N4 C18 C19 122.0(5) . . ?
N4 C18 C17 115.5(4) . . ?
C19 C18 C17 122.5(5) . . ?
C18 C19 C20 118.1(5) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 119.1(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N4 C22 C21 121.1(5) . . ?
N4 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
H2A O2W H2B 118.0 . . ?
H3A O3W H3B 128.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Cu1 O1 C1 83.3(4) 2_666 . . . ?
N3 Cu1 O1 C1 -93.0(4) . . . . ?
O1W Cu1 O1 C1 176.7(4) . . . . ?
O1 Cu1 N3 C17 178.9(4) . . . . ?
N4 Cu1 N3 C17 6.6(3) . . . . ?
O1W Cu1 N3 C17 -89.0(4) . . . . ?
O1 Cu1 N3 C13 -8.0(5) . . . . ?
N4 Cu1 N3 C13 179.6(5) . . . . ?
O1W Cu1 N3 C13 84.1(5) . . . . ?
O3 Cu1 N4 C18 179.6(4) 2_666 . . . ?
N3 Cu1 N4 C18 -3.3(4) . . . . ?
O1W Cu1 N4 C18 85.9(4) . . . . ?
O3 Cu1 N4 C22 -3.0(4) 2_666 . . . ?
N3 Cu1 N4 C22 174.1(4) . . . . ?
O1W Cu1 N4 C22 -96.7(4) . . . . ?
Cu1 O1 C1 O2 9.7(7) . . . . ?
Cu1 O1 C1 C2 -172.2(3) . . . . ?
O2 C1 C2 C3 -154.2(5) . . . . ?
O1 C1 C2 C3 27.6(7) . . . . ?
O2 C1 C2 C6 26.6(7) . . . . ?
O1 C1 C2 C6 -151.6(5) . . . . ?
C6 C2 C3 C4 0.8(7) . . . . ?
C1 C2 C3 C4 -178.4(5) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 N1 0.2(8) . . . . ?
O5 N1 C5 C4 177.9(5) . . . . ?
C6 N1 C5 C4 -1.6(8) . . . . ?
O5 N1 C6 C2 -177.0(4) . . . . ?
C5 N1 C6 C2 2.6(7) . . . . ?
O5 N1 C6 C7 -4.5(6) . . . . ?
C5 N1 C6 C7 175.0(4) . . . . ?
C3 C2 C6 N1 -2.2(7) . . . . ?
C1 C2 C6 N1 177.0(4) . . . . ?
C3 C2 C6 C7 -173.7(4) . . . . ?
C1 C2 C6 C7 5.5(7) . . . . ?
O6 N2 C7 C11 -179.5(5) . . . . ?
C8 N2 C7 C11 0.9(7) . . . . ?
O6 N2 C7 C6 -0.3(7) . . . . ?
C8 N2 C7 C6 -179.9(5) . . . . ?
N1 C6 C7 N2 -93.0(5) . . . . ?
C2 C6 C7 N2 79.0(6) . . . . ?
N1 C6 C7 C11 86.2(6) . . . . ?
C2 C6 C7 C11 -101.8(6) . . . . ?
O6 N2 C8 C9 178.7(5) . . . . ?
C7 N2 C8 C9 -1.6(8) . . . . ?
N2 C8 C9 C10 1.3(9) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C7 -0.5(8) . . . . ?
C9 C10 C11 C12 179.7(5) . . . . ?
N2 C7 C11 C10 0.2(7) . . . . ?
C6 C7 C11 C10 -178.9(5) . . . . ?
N2 C7 C11 C12 180.0(4) . . . . ?
C6 C7 C11 C12 0.9(8) . . . . ?
Cu1 O3 C12 O4 -15.7(8) 2_666 . . . ?
Cu1 O3 C12 C11 165.6(3) 2_666 . . . ?
C10 C11 C12 O4 -8.3(7) . . . . ?
C7 C11 C12 O4 171.9(5) . . . . ?
C10 C11 C12 O3 170.4(5) . . . . ?
C7 C11 C12 O3 -9.3(7) . . . . ?
C17 N3 C13 C14 0.1(8) . . . . ?
Cu1 N3 C13 C14 -172.7(4) . . . . ?
N3 C13 C14 C15 1.2(9) . . . . ?
C13 C14 C15 C16 -1.2(9) . . . . ?
C14 C15 C16 C17 -0.1(9) . . . . ?
C13 N3 C17 C16 -1.5(7) . . . . ?
Cu1 N3 C17 C16 172.1(4) . . . . ?
C13 N3 C17 C18 178.1(4) . . . . ?
Cu1 N3 C17 C18 -8.3(5) . . . . ?
C15 C16 C17 N3 1.5(8) . . . . ?
C15 C16 C17 C18 -178.1(5) . . . . ?
C22 N4 C18 C19 1.6(8) . . . . ?
Cu1 N4 C18 C19 179.1(4) . . . . ?
C22 N4 C18 C17 -177.6(4) . . . . ?
Cu1 N4 C18 C17 -0.1(6) . . . . ?
N3 C17 C18 N4 5.6(6) . . . . ?
C16 C17 C18 N4 -174.8(5) . . . . ?
N3 C17 C18 C19 -173.6(5) . . . . ?
C16 C17 C18 C19 6.0(8) . . . . ?
N4 C18 C19 C20 -1.3(8) . . . . ?
C17 C18 C19 C20 177.8(5) . . . . ?
C18 C19 C20 C21 -0.2(8) . . . . ?
C19 C20 C21 C22 1.4(8) . . . . ?
C18 N4 C22 C21 -0.3(8) . . . . ?
Cu1 N4 C22 C21 -177.6(4) . . . . ?
C20 C21 C22 N4 -1.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.168
_database_code_depnum_ccdc_archive 'CCDC 1018476'
