# 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_1a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Cu N4 O'
_chemical_formula_weight         318.84

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.6688(3)
_cell_length_b                   11.4952(3)
_cell_length_c                   12.9734(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.7220(10)
_cell_angle_gamma                90.00
_cell_volume                     1523.77(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7805
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.23

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    1.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_T_max  0.7625
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13493
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         28.25
_reflns_number_total             3752
_reflns_number_gt                2991
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.5801P] 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         3752
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cu Cu 0.42339(2) 0.58461(2) 0.463020(19) 0.03027(10) Uani 1 1 d . . .
O O 0.1950(6) 0.1355(3) 0.5093(4) 0.194(2) Uani 1 1 d . . .
N1 N -0.1086(2) 0.5051(3) 0.2946(2) 0.0703(7) Uani 1 1 d . . .
N2 N 0.28669(16) 0.47938(15) 0.47834(13) 0.0306(4) Uani 1 1 d . . .
N3 N 0.44270(16) 0.37523(15) 0.60563(13) 0.0297(3) Uani 1 1 d . . .
N4 N 0.53773(18) 0.19051(17) 0.89766(15) 0.0408(4) Uani 1 1 d . . .
C1 C -0.0285(3) 0.5948(3) 0.3138(3) 0.0681(9) Uani 1 1 d . . .
H1A H -0.0620 0.6662 0.2849 0.082 Uiso 1 1 calc R . .
C2 C 0.1022(3) 0.5909(2) 0.3739(2) 0.0512(6) Uani 1 1 d . . .
H2A H 0.1536 0.6576 0.3840 0.061 Uiso 1 1 calc R . .
C3 C 0.15447(19) 0.48593(19) 0.41846(16) 0.0336(4) Uani 1 1 d . . .
C4 C 0.0716(2) 0.3908(2) 0.3975(2) 0.0489(6) Uani 1 1 d . . .
H4B H 0.1020 0.3179 0.4244 0.059 Uiso 1 1 calc R . .
C5 C -0.0563(3) 0.4054(3) 0.3363(3) 0.0645(8) Uani 1 1 d . . .
H5A H -0.1100 0.3400 0.3235 0.077 Uiso 1 1 calc R . .
C6 C 0.31932(19) 0.40273(16) 0.55753(16) 0.0298(4) Uani 1 1 d . . .
H6A H 0.2535 0.3671 0.5801 0.036 Uiso 1 1 calc R . .
C7 C 0.4368(2) 0.2653(2) 0.87155(18) 0.0420(5) Uani 1 1 d . . .
H7A H 0.3888 0.2757 0.9204 0.050 Uiso 1 1 calc R . .
C8 C 0.4001(2) 0.3275(2) 0.77706(17) 0.0384(5) Uani 1 1 d . . .
H8A H 0.3295 0.3784 0.7635 0.046 Uiso 1 1 calc R . .
C9 C 0.46943(19) 0.31368(17) 0.70151(16) 0.0309(4) Uani 1 1 d . . .
C10 C 0.5742(2) 0.2361(2) 0.72893(18) 0.0407(5) Uani 1 1 d . . .
H10A H 0.6247 0.2244 0.6821 0.049 Uiso 1 1 calc R . .
C11 C 0.6031(2) 0.1770(2) 0.82427(19) 0.0454(6) Uani 1 1 d . . .
H11A H 0.6722 0.1244 0.8392 0.054 Uiso 1 1 calc R . .
C12 C 0.2305(9) 0.0264(6) 0.6630(5) 0.208(4) Uani 1 1 d . . .
H12A H 0.2097 0.0969 0.6941 0.312 Uiso 1 1 calc R . .
H12B H 0.3183 0.0032 0.7003 0.312 Uiso 1 1 calc R . .
H12C H 0.1707 -0.0338 0.6692 0.312 Uiso 1 1 calc R . .
C13 C 0.2200(6) 0.0454(4) 0.5519(4) 0.1243(18) Uani 1 1 d . . .
C14 C 0.2554(12) -0.0507(7) 0.4942(6) 0.289(7) Uani 1 1 d . . .
H14A H 0.2352 -0.0315 0.4192 0.434 Uiso 1 1 calc R . .
H14B H 0.2072 -0.1187 0.5028 0.434 Uiso 1 1 calc R . .
H14C H 0.3475 -0.0658 0.5223 0.434 Uiso 1 1 calc 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
Cu N3 1.9441(16) 3_666 ?
Cu N2 1.9484(17) . ?
Cu N4 2.1189(17) 2_656 ?
Cu Cu 2.5444(5) 3_666 ?
O C13 1.167(5) . ?
N1 C1 1.316(4) . ?
N1 C5 1.321(4) . ?
N2 C6 1.322(2) . ?
N2 C3 1.403(2) . ?
N3 C6 1.323(2) . ?
N3 C9 1.387(2) . ?
N3 Cu 1.9441(16) 3_666 ?
N4 C11 1.341(3) . ?
N4 C7 1.343(3) . ?
N4 Cu 2.1189(17) 2_646 ?
C1 C2 1.388(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(3) . ?
C4 C5 1.378(4) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.375(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.397(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.394(3) . ?
C10 C11 1.366(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.430(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.445(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N3 Cu N2 149.82(7) 3_666 . ?
N3 Cu N4 105.37(7) 3_666 2_656 ?
N2 Cu N4 103.78(7) . 2_656 ?
N3 Cu Cu 82.95(5) 3_666 3_666 ?
N2 Cu Cu 84.58(5) . 3_666 ?
N4 Cu Cu 99.83(6) 2_656 3_666 ?
C1 N1 C5 115.4(2) . . ?
C6 N2 C3 117.65(17) . . ?
C6 N2 Cu 117.11(13) . . ?
C3 N2 Cu 124.96(13) . . ?
C6 N3 C9 117.69(16) . . ?
C6 N3 Cu 119.34(13) . 3_666 ?
C9 N3 Cu 122.90(13) . 3_666 ?
C11 N4 C7 115.98(18) . . ?
C11 N4 Cu 121.66(14) . 2_646 ?
C7 N4 Cu 121.93(14) . 2_646 ?
N1 C1 C2 125.0(3) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C4 C3 C2 116.7(2) . . ?
C4 C3 N2 123.4(2) . . ?
C2 C3 N2 119.9(2) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4B 120.4 . . ?
C3 C4 H4B 120.4 . . ?
N1 C5 C4 124.9(3) . . ?
N1 C5 H5A 117.5 . . ?
C4 C5 H5A 117.5 . . ?
N2 C6 N3 121.99(18) . . ?
N2 C6 H6A 119.0 . . ?
N3 C6 H6A 119.0 . . ?
N4 C7 C8 124.03(19) . . ?
N4 C7 H7A 118.0 . . ?
C8 C7 H7A 118.0 . . ?
C7 C8 C9 119.61(19) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
N3 C9 C10 119.86(17) . . ?
N3 C9 C8 123.88(18) . . ?
C10 C9 C8 116.20(18) . . ?
C11 C10 C9 120.28(18) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
N4 C11 C10 123.9(2) . . ?
N4 C11 H11A 118.1 . . ?
C10 C11 H11A 118.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O C13 C12 123.6(6) . . ?
O C13 C14 119.4(6) . . ?
C12 C13 C14 116.7(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1017750'
#######################################################################
#
#                 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_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cu N5 O'
_chemical_formula_weight         333.86

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)/c

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

_cell_length_a                   9.4249(2)
_cell_length_b                   14.2699(4)
_cell_length_c                   11.4988(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.7050(10)
_cell_angle_gamma                90.00
_cell_volume                     1519.59(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9535
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.31

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_T_max  0.6714
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14033
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.32
_reflns_number_total             3757
_reflns_number_gt                3231
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.8952P] 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         3757
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Cu Cu 0.54187(3) 0.085003(16) 0.00736(2) 0.02912(10) Uani 1 1 d . . .
O O -0.1456(9) -0.4972(4) 0.1328(4) 0.243(4) Uani 1 1 d . . .
N4 N 0.4838(2) 0.31348(13) 0.37090(16) 0.0358(4) Uani 1 1 d . . .
N2 N 0.40634(19) 0.09822(11) 0.11525(15) 0.0288(3) Uani 1 1 d . . .
N3 N 0.28376(18) -0.03329(12) 0.03740(14) 0.0287(3) Uani 1 1 d . . .
N1 N -0.0740(3) -0.21754(18) -0.0053(2) 0.0575(6) Uani 1 1 d . . .
N5 N -0.2241(5) -0.5119(3) -0.0671(4) 0.1058(13) Uani 1 1 d . . .
C1 C 0.5492(3) 0.30903(16) 0.2768(2) 0.0400(5) Uani 1 1 d . . .
H1A H 0.6170 0.3549 0.2693 0.048 Uiso 1 1 calc R . .
C2 C 0.5223(2) 0.24104(16) 0.19088(18) 0.0374(5) Uani 1 1 d . . .
H2A H 0.5715 0.2420 0.1279 0.045 Uiso 1 1 calc R . .
C3 C 0.4213(2) 0.17033(14) 0.19768(16) 0.0286(4) Uani 1 1 d . . .
C4 C 0.3486(2) 0.17653(16) 0.29344(19) 0.0364(5) Uani 1 1 d . . .
H4A H 0.2775 0.1331 0.3017 0.044 Uiso 1 1 calc R . .
C5 C 0.3833(2) 0.24749(16) 0.37522(19) 0.0364(5) Uani 1 1 d . . .
H5A H 0.3335 0.2498 0.4378 0.044 Uiso 1 1 calc R . .
C6 C 0.2923(2) 0.04181(13) 0.10441(17) 0.0288(4) Uani 1 1 d . . .
H6A H 0.2179 0.0557 0.1446 0.035 Uiso 1 1 calc R . .
C7 C -0.0415(3) -0.1621(2) 0.0887(3) 0.0524(6) Uani 1 1 d . . .
H7A H -0.0998 -0.1661 0.1455 0.063 Uiso 1 1 calc R . .
C8 C 0.0712(3) -0.09917(18) 0.1089(2) 0.0440(5) Uani 1 1 d . . .
H8A H 0.0872 -0.0626 0.1770 0.053 Uiso 1 1 calc R . .
C9 C 0.1611(2) -0.09106(14) 0.02592(19) 0.0313(4) Uani 1 1 d . . .
C10 C 0.1279(3) -0.14777(19) -0.0734(2) 0.0479(6) Uani 1 1 d . . .
H10A H 0.1837 -0.1452 -0.1321 0.057 Uiso 1 1 calc R . .
C11 C 0.0107(3) -0.2085(2) -0.0846(3) 0.0606(8) Uani 1 1 d . . .
H11A H -0.0095 -0.2454 -0.1524 0.073 Uiso 1 1 calc R . .
C12 C -0.2485(10) -0.6046(6) -0.0495(11) 0.261(7) Uani 1 1 d . . .
H12A H -0.2282 -0.6180 0.0337 0.391 Uiso 1 1 calc R . .
H12B H -0.1870 -0.6418 -0.0888 0.391 Uiso 1 1 calc R . .
H12C H -0.3477 -0.6191 -0.0810 0.391 Uiso 1 1 calc R . .
C13 C -0.2411(8) -0.4681(5) -0.1791(5) 0.156(3) Uani 1 1 d . . .
H13A H -0.2231 -0.4022 -0.1687 0.234 Uiso 1 1 calc R . .
H13B H -0.3379 -0.4778 -0.2213 0.234 Uiso 1 1 calc R . .
H13C H -0.1740 -0.4946 -0.2233 0.234 Uiso 1 1 calc R . .
C14 C -0.1674(7) -0.4667(5) 0.0309(5) 0.1245(18) Uani 1 1 d . . .
H14A H -0.1412 -0.4025 0.0212 0.149 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
Cu N2 1.9481(17) . ?
Cu N3 1.9557(16) 3_655 ?
Cu N4 2.1310(17) 4_565 ?
Cu Cu 2.5470(5) 3_655 ?
O C14 1.231(7) . ?
N4 C1 1.342(3) . ?
N4 C5 1.343(3) . ?
N4 Cu 2.1310(17) 4_566 ?
N2 C6 1.330(3) . ?
N2 C3 1.388(2) . ?
N3 C6 1.314(3) . ?
N3 C9 1.406(3) . ?
N3 Cu 1.9557(16) 3_655 ?
N1 C11 1.324(4) . ?
N1 C7 1.328(4) . ?
N5 C14 1.323(7) . ?
N5 C12 1.363(7) . ?
N5 C13 1.413(7) . ?
C1 C2 1.375(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.399(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(3) . ?
C4 C5 1.379(3) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.393(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.387(3) . ?
C10 C11 1.391(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu N3 152.45(7) . 3_655 ?
N2 Cu N4 107.10(7) . 4_565 ?
N3 Cu N4 100.15(7) 3_655 4_565 ?
N2 Cu Cu 84.42(5) . 3_655 ?
N3 Cu Cu 83.58(5) 3_655 3_655 ?
N4 Cu Cu 124.37(6) 4_565 3_655 ?
C1 N4 C5 115.42(18) . . ?
C1 N4 Cu 122.15(15) . 4_566 ?
C5 N4 Cu 122.39(14) . 4_566 ?
C6 N2 C3 119.36(17) . . ?
C6 N2 Cu 119.73(13) . . ?
C3 N2 Cu 120.74(13) . . ?
C6 N3 C9 119.52(17) . . ?
C6 N3 Cu 119.97(14) . 3_655 ?
C9 N3 Cu 118.08(13) . 3_655 ?
C11 N1 C7 115.1(2) . . ?
C14 N5 C12 113.6(6) . . ?
C14 N5 C13 121.3(5) . . ?
C12 N5 C13 124.8(7) . . ?
N4 C1 C2 124.2(2) . . ?
N4 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 120.34(19) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
N2 C3 C2 118.69(17) . . ?
N2 C3 C4 125.44(18) . . ?
C2 C3 C4 115.77(18) . . ?
C5 C4 C3 119.51(19) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N4 C5 C4 124.68(19) . . ?
N4 C5 H5A 117.7 . . ?
C4 C5 H5A 117.7 . . ?
N3 C6 N2 120.58(18) . . ?
N3 C6 H6A 119.7 . . ?
N2 C6 H6A 119.7 . . ?
N1 C7 C8 125.4(3) . . ?
N1 C7 H7A 117.3 . . ?
C8 C7 H7A 117.3 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 116.3(2) . . ?
C10 C9 N3 118.4(2) . . ?
C8 C9 N3 125.3(2) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
N1 C11 C10 124.5(3) . . ?
N1 C11 H11A 117.7 . . ?
C10 C11 H11A 117.7 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O C14 N5 127.4(7) . . ?
O C14 H14A 116.6 . . ?
N5 C14 H14A 116.1 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 1017751'
#######################################################################
#
#                 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_1c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N4 O'
_chemical_formula_weight         332.87

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.5252(2)
_cell_length_b                   11.1791(2)
_cell_length_c                   13.0198(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.2320(10)
_cell_angle_gamma                90.00
_cell_volume                     1470.87(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8777
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.29

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    1.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13271
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.29
_reflns_number_total             3628
_reflns_number_gt                3169
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.8253P] 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         3628
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Cu Cu 0.419160(16) 0.583420(16) 0.461520(13) 0.01126(5) Uani 1 1 d . . .
N1 N -0.11712(13) 0.48806(14) 0.29032(12) 0.0246(3) Uani 1 1 d . . .
N2 N 0.28284(12) 0.47197(11) 0.47474(10) 0.0121(2) Uani 1 1 d . . .
N3 N 0.44264(12) 0.36861(11) 0.60221(9) 0.0117(2) Uani 1 1 d . . .
N4 N 0.53834(12) 0.18344(12) 0.89517(10) 0.0153(3) Uani 1 1 d . . .
C1 C -0.03661(17) 0.58337(15) 0.30762(14) 0.0221(4) Uani 1 1 d . . .
H1A H -0.0714 0.6558 0.2773 0.027 Uiso 1 1 calc R . .
C2 C 0.09424(16) 0.58148(14) 0.36734(13) 0.0181(3) Uani 1 1 d . . .
H2A H 0.1449 0.6508 0.3757 0.022 Uiso 1 1 calc R . .
C3 C 0.15039(14) 0.47462(13) 0.41526(11) 0.0130(3) Uani 1 1 d . . .
C4 C 0.06831(15) 0.37345(15) 0.39597(13) 0.0183(3) Uani 1 1 d . . .
H4A H 0.1007 0.2994 0.4239 0.022 Uiso 1 1 calc R . .
C5 C -0.06143(17) 0.38551(16) 0.33483(15) 0.0242(4) Uani 1 1 d . . .
H5A H -0.1143 0.3174 0.3236 0.029 Uiso 1 1 calc R . .
C6 C 0.31724(14) 0.39361(13) 0.55446(11) 0.0122(3) Uani 1 1 d . . .
H6A H 0.2514 0.3554 0.5772 0.015 Uiso 1 1 calc R . .
C7 C 0.47002(14) 0.30609(13) 0.69865(11) 0.0121(3) Uani 1 1 d . . .
C8 C 0.40273(15) 0.32703(14) 0.77602(12) 0.0147(3) Uani 1 1 d . . .
H8A H 0.3341 0.3823 0.7634 0.018 Uiso 1 1 calc R . .
C9 C 0.43993(15) 0.26437(14) 0.87119(12) 0.0156(3) Uani 1 1 d . . .
H9A H 0.3943 0.2790 0.9216 0.019 Uiso 1 1 calc R . .
C10 C 0.60138(15) 0.16289(14) 0.82001(12) 0.0169(3) Uani 1 1 d . . .
H10A H 0.6683 0.1058 0.8342 0.020 Uiso 1 1 calc R . .
C11 C 0.57226(15) 0.22178(14) 0.72329(12) 0.0157(3) Uani 1 1 d . . .
H11A H 0.6202 0.2056 0.6748 0.019 Uiso 1 1 calc R . .
O O 0.2258(2) 0.10978(15) 0.52906(16) 0.0577(5) Uani 1 1 d . . .
C12 C 0.2781(3) 0.0077(2) 0.4924(2) 0.0510(6) Uani 1 1 d . . .
H12A H 0.3700 -0.0036 0.5322 0.061 Uiso 1 1 calc R . .
H12B H 0.2726 0.0156 0.4171 0.061 Uiso 1 1 calc R . .
C13 C 0.1964(2) -0.09445(19) 0.50992(18) 0.0384(5) Uani 1 1 d . . .
H13A H 0.2467 -0.1683 0.5205 0.046 Uiso 1 1 calc R . .
H13B H 0.1181 -0.1042 0.4499 0.046 Uiso 1 1 calc R . .
C14 C 0.1591(2) -0.0587(2) 0.6116(2) 0.0419(5) Uani 1 1 d . . .
H14A H 0.0646 -0.0669 0.6016 0.050 Uiso 1 1 calc R . .
H14B H 0.2061 -0.1071 0.6721 0.050 Uiso 1 1 calc R . .
C15 C 0.2015(3) 0.0715(2) 0.6274(2) 0.0590(7) Uani 1 1 d . . .
H15A H 0.1323 0.1195 0.6428 0.071 Uiso 1 1 calc R . .
H15B H 0.2811 0.0792 0.6865 0.071 Uiso 1 1 calc 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
Cu N3 1.9408(12) 3_666 ?
Cu N2 1.9439(12) . ?
Cu N4 2.1131(13) 2_656 ?
Cu Cu 2.5348(3) 3_666 ?
N1 C1 1.341(2) . ?
N1 C5 1.343(2) . ?
N2 C6 1.3288(19) . ?
N2 C3 1.3930(18) . ?
N3 C6 1.3221(19) . ?
N3 C7 1.3949(18) . ?
N3 Cu 1.9408(12) 3_666 ?
N4 C9 1.3446(19) . ?
N4 C10 1.347(2) . ?
N4 Cu 2.1131(13) 2_646 ?
C1 C2 1.380(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.400(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.403(2) . ?
C4 C5 1.382(2) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C11 1.399(2) . ?
C7 C8 1.404(2) . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
O C12 1.406(3) . ?
O C15 1.439(4) . ?
C12 C13 1.485(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.535(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu N2 151.04(5) 3_666 . ?
N3 Cu N4 103.43(5) 3_666 2_656 ?
N2 Cu N4 103.90(5) . 2_656 ?
N3 Cu Cu 82.63(4) 3_666 3_666 ?
N2 Cu Cu 85.64(4) . 3_666 ?
N4 Cu Cu 95.01(4) 2_656 3_666 ?
C1 N1 C5 115.26(14) . . ?
C6 N2 C3 117.39(12) . . ?
C6 N2 Cu 116.42(10) . . ?
C3 N2 Cu 125.87(10) . . ?
C6 N3 C7 117.20(12) . . ?
C6 N3 Cu 120.63(10) . 3_666 ?
C7 N3 Cu 122.16(9) . 3_666 ?
C9 N4 C10 116.75(13) . . ?
C9 N4 Cu 121.35(10) . 2_646 ?
C10 N4 Cu 121.71(10) . 2_646 ?
N1 C1 C2 124.55(15) . . ?
N1 C1 H1A 117.7 . . ?
C2 C1 H1A 117.7 . . ?
C1 C2 C3 119.66(15) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
N2 C3 C2 119.88(13) . . ?
N2 C3 C4 123.57(13) . . ?
C2 C3 C4 116.50(14) . . ?
C5 C4 C3 118.99(15) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N1 C5 C4 125.01(16) . . ?
N1 C5 H5A 117.5 . . ?
C4 C5 H5A 117.5 . . ?
N3 C6 N2 121.66(14) . . ?
N3 C6 H6A 119.2 . . ?
N2 C6 H6A 119.2 . . ?
N3 C7 C11 119.75(13) . . ?
N3 C7 C8 122.94(13) . . ?
C11 C7 C8 117.26(13) . . ?
C9 C8 C7 119.07(14) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
N4 C9 C8 123.80(14) . . ?
N4 C9 H9A 118.1 . . ?
C8 C9 H9A 118.1 . . ?
N4 C10 C11 123.63(14) . . ?
N4 C10 H10A 118.2 . . ?
C11 C10 H10A 118.2 . . ?
C10 C11 C7 119.48(14) . . ?
C10 C11 H11A 120.3 . . ?
C7 C11 H11A 120.3 . . ?
C12 O C15 104.13(19) . . ?
O C12 C13 105.9(2) . . ?
O C12 H12A 110.6 . . ?
C13 C12 H12A 110.6 . . ?
O C12 H12B 110.6 . . ?
C13 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 C14 103.35(19) . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C13 103.3(2) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
O C15 C14 106.4(2) . . ?
O C15 H15A 110.4 . . ?
C14 C15 H15A 110.4 . . ?
O C15 H15B 110.4 . . ?
C14 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 1017752'
#######################################################################
#
#                 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_2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H44 Cu4 N16 O2'
_chemical_formula_weight         1107.13

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   C2/c

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

_cell_length_a                   20.8634(7)
_cell_length_b                   21.3369(8)
_cell_length_c                   22.7994(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.646(2)
_cell_angle_gamma                90.00
_cell_volume                     10034.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.89

_exptl_crystal_description       PLATE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4512
_exptl_absorpt_coefficient_mu    1.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5451
_exptl_absorpt_correction_T_max  0.7817
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49171
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         28.31
_reflns_number_total             12385
_reflns_number_gt                7469
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0948P)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         12385
_refine_ls_number_parameters     640
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1776
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11320(2) 0.18791(2) 0.788233(19) 0.02380(12) Uani 1 1 d . . .
Cu2 Cu 0.09915(2) 0.08675(2) 0.731584(19) 0.03007(13) Uani 1 1 d . . .
Cu3 Cu 0.54510(2) 0.02265(3) 0.71866(2) 0.03035(13) Uani 1 1 d . . .
Cu4 Cu 0.44289(2) 0.24821(2) 0.723627(18) 0.02280(12) Uani 1 1 d . . .
N1 N 0.09941(19) 0.23659(19) 1.01764(16) 0.0426(10) Uani 1 1 d . . .
N2 N 0.09926(14) 0.13676(16) 0.85711(12) 0.0241(7) Uani 1 1 d . . .
N3 N 0.09183(14) 0.04345(16) 0.80478(13) 0.0237(7) Uani 1 1 d . . .
N4 N 0.07576(15) -0.15409(16) 0.79239(13) 0.0274(8) Uani 1 1 d . . .
N5 N 0.06046(16) 0.42692(17) 0.70999(14) 0.0309(8) Uani 1 1 d . . .
N6 N 0.07904(14) 0.22907(16) 0.71255(13) 0.0229(7) Uani 1 1 d . . .
N7 N 0.07396(14) 0.13572(16) 0.66085(12) 0.0249(8) Uani 1 1 d . . .
N8 N 0.0880(2) 0.0353(2) 0.50323(15) 0.0517(12) Uani 1 1 d . . .
N9 N 0.20070(18) 0.0702(2) 0.72193(18) 0.0509(11) Uani 1 1 d . . .
N10 N 0.39851(16) 0.04854(17) 0.70908(15) 0.0313(8) Uani 1 1 d . . .
N11 N 0.48132(16) 0.05145(17) 0.65256(14) 0.0306(8) Uani 1 1 d . . .
N12 N 0.5421(3) 0.0864(2) 0.48751(17) 0.0581(13) Uani 1 1 d . . .
N13 N 0.21371(14) 0.21064(17) 0.80017(13) 0.0276(8) Uani 1 1 d . . .
N14 N 0.41628(13) 0.23021(15) 0.80019(13) 0.0224(7) Uani 1 1 d . . .
N15 N 0.52225(14) 0.22697(16) 0.84863(13) 0.0237(7) Uani 1 1 d . . .
N16 N 0.65712(17) 0.2100(2) 1.00594(15) 0.0450(11) Uani 1 1 d . . .
C1 C 0.1097(3) 0.2626(2) 0.9665(2) 0.0569(15) Uani 1 1 d . . .
H1A H 0.1172 0.3056 0.9661 0.068 Uiso 1 1 calc R . .
C2 C 0.1100(2) 0.2303(2) 0.91503(19) 0.0463(13) Uani 1 1 d . . .
H2A H 0.1177 0.2518 0.8813 0.056 Uiso 1 1 calc R . .
C3 C 0.09914(17) 0.1672(2) 0.91165(15) 0.0250(9) Uani 1 1 d . . .
C4 C 0.0856(4) 0.1402(3) 0.9640(2) 0.080(2) Uani 1 1 d . . .
H4A H 0.0757 0.0977 0.9652 0.097 Uiso 1 1 calc R . .
C5 C 0.0869(3) 0.1764(3) 1.0138(2) 0.076(2) Uani 1 1 d . . .
H5A H 0.0780 0.1565 1.0480 0.091 Uiso 1 1 calc R . .
C6 C 0.09352(17) 0.0750(2) 0.85515(16) 0.0262(9) Uani 1 1 d . . .
H6A H 0.0906 0.0532 0.8899 0.031 Uiso 1 1 calc R . .
C7 C 0.08929(19) -0.1169(2) 0.74836(15) 0.0285(9) Uani 1 1 d . . .
H7A H 0.0950 -0.1357 0.7127 0.034 Uiso 1 1 calc R . .
C8 C 0.09527(19) -0.0535(2) 0.75246(16) 0.0292(10) Uani 1 1 d . . .
H8A H 0.1053 -0.0308 0.7202 0.035 Uiso 1 1 calc R . .
C9 C 0.08647(17) -0.02147(19) 0.80469(15) 0.0238(9) Uani 1 1 d . . .
C10 C 0.07175(18) -0.0594(2) 0.85065(15) 0.0271(9) Uani 1 1 d . . .
H10A H 0.0652 -0.0417 0.8865 0.033 Uiso 1 1 calc R . .
C11 C 0.06695(18) -0.1235(2) 0.84245(16) 0.0267(9) Uani 1 1 d . . .
H11A H 0.0568 -0.1474 0.8739 0.032 Uiso 1 1 calc R . .
C12 C 0.09693(19) 0.3945(2) 0.75420(16) 0.0304(10) Uani 1 1 d . . .
H12A H 0.1191 0.4172 0.7857 0.037 Uiso 1 1 calc R . .
C13 C 0.10327(18) 0.3311(2) 0.75567(16) 0.0284(9) Uani 1 1 d . . .
H13A H 0.1291 0.3121 0.7875 0.034 Uiso 1 1 calc R . .
C14 C 0.07115(17) 0.29443(19) 0.70949(16) 0.0245(9) Uani 1 1 d . . .
C15 C 0.03187(18) 0.3270(2) 0.66400(16) 0.0299(10) Uani 1 1 d . . .
H15A H 0.0081 0.3054 0.6326 0.036 Uiso 1 1 calc R . .
C16 C 0.02892(19) 0.3914(2) 0.66648(17) 0.0330(10) Uani 1 1 d . . .
H16A H 0.0030 0.4119 0.6355 0.040 Uiso 1 1 calc R . .
C17 C 0.06973(17) 0.1967(2) 0.66239(16) 0.0263(9) Uani 1 1 d . . .
H17A H 0.0598 0.2184 0.6268 0.032 Uiso 1 1 calc R . .
C22 C 0.1030(3) 0.0952(3) 0.50845(19) 0.0491(13) Uani 1 1 d . . .
H22A H 0.1174 0.1144 0.4762 0.059 Uiso 1 1 calc R . .
C21 C 0.0990(2) 0.1321(2) 0.55776(17) 0.0393(11) Uani 1 1 d . . .
H21A H 0.1119 0.1738 0.5584 0.047 Uiso 1 1 calc R . .
C20 C 0.07544(19) 0.1059(2) 0.60675(16) 0.0294(10) Uani 1 1 d . . .
C19 C 0.0580(2) 0.0423(2) 0.60141(16) 0.0337(10) Uani 1 1 d . . .
H19A H 0.0417 0.0222 0.6322 0.040 Uiso 1 1 calc R . .
C18 C 0.0651(2) 0.0099(2) 0.55055(19) 0.0445(12) Uani 1 1 d . . .
H18A H 0.0533 -0.0322 0.5485 0.053 Uiso 1 1 calc R . .
C34 C 0.25659(18) 0.1933(2) 0.84681(17) 0.0349(11) Uani 1 1 d . . .
H34A H 0.2404 0.1757 0.8789 0.042 Uiso 1 1 calc R . .
C35 C 0.32280(18) 0.1994(2) 0.85139(17) 0.0341(11) Uani 1 1 d . . .
H35A H 0.3496 0.1873 0.8859 0.041 Uiso 1 1 calc R . .
C36 C 0.34930(17) 0.2241(2) 0.80359(16) 0.0241(9) Uani 1 1 d . . .
C37 C 0.30545(18) 0.2437(2) 0.75510(17) 0.0353(11) Uani 1 1 d . . .
H37A H 0.3203 0.2616 0.7225 0.042 Uiso 1 1 calc R . .
C38 C 0.23980(18) 0.2363(2) 0.75547(16) 0.0342(11) Uani 1 1 d . . .
H38A H 0.2117 0.2500 0.7224 0.041 Uiso 1 1 calc R . .
C39 C 0.45899(17) 0.22389(19) 0.84900(15) 0.0239(9) Uani 1 1 d . . .
H39A H 0.4440 0.2170 0.8849 0.029 Uiso 1 1 calc R . .
C44 C 0.6732(2) 0.2177(3) 0.9524(2) 0.071(2) Uani 1 1 d . . .
H44A H 0.7171 0.2204 0.9495 0.085 Uiso 1 1 calc R . .
C43 C 0.6297(2) 0.2222(3) 0.90056(19) 0.0608(18) Uani 1 1 d . . .
H43A H 0.6449 0.2262 0.8644 0.073 Uiso 1 1 calc R . .
C42 C 0.56416(18) 0.2208(2) 0.90193(16) 0.0255(9) Uani 1 1 d . . .
C41 C 0.54710(19) 0.2147(2) 0.95852(17) 0.0341(11) Uani 1 1 d . . .
H41A H 0.5037 0.2149 0.9635 0.041 Uiso 1 1 calc R . .
C40 C 0.5944(2) 0.2085(2) 1.00677(17) 0.0347(11) Uani 1 1 d . . .
H40A H 0.5809 0.2026 1.0434 0.042 Uiso 1 1 calc R . .
C27 C 0.2410(2) 0.0419(3) 0.7616(2) 0.0453(13) Uani 1 1 d . . .
H27A H 0.2253 0.0253 0.7943 0.054 Uiso 1 1 calc R . .
C26 C 0.3062(2) 0.0347(3) 0.75838(19) 0.0482(14) Uani 1 1 d . . .
H26A H 0.3326 0.0140 0.7888 0.058 Uiso 1 1 calc R . .
C25 C 0.33274(19) 0.0575(2) 0.71147(19) 0.0344(10) Uani 1 1 d . . .
C24 C 0.2918(3) 0.0925(4) 0.6725(3) 0.091(2) Uani 1 1 d . . .
H24A H 0.3073 0.1122 0.6410 0.109 Uiso 1 1 calc R . .
C23 C 0.2271(3) 0.0991(4) 0.6792(3) 0.091(2) Uani 1 1 d . . .
H23A H 0.2009 0.1248 0.6527 0.109 Uiso 1 1 calc R . .
C28 C 0.4203(2) 0.0591(2) 0.65893(18) 0.0310(10) Uani 1 1 d . . .
H28A H 0.3912 0.0725 0.6264 0.037 Uiso 1 1 calc R . .
C29 C 0.5815(3) 0.0865(3) 0.5380(2) 0.0614(16) Uani 1 1 d . . .
H29A H 0.6251 0.0943 0.5368 0.074 Uiso 1 1 calc R . .
C30 C 0.5631(2) 0.0759(2) 0.5934(2) 0.0491(13) Uani 1 1 d . . .
H30A H 0.5934 0.0780 0.6277 0.059 Uiso 1 1 calc R . .
C31 C 0.4989(2) 0.0622(2) 0.59621(18) 0.0358(10) Uani 1 1 d . . .
C32 C 0.4577(2) 0.0607(2) 0.5429(2) 0.0489(13) Uani 1 1 d . . .
H32A H 0.4140 0.0520 0.5422 0.059 Uiso 1 1 calc R . .
C33 C 0.4807(3) 0.0719(3) 0.4918(2) 0.0578(15) Uani 1 1 d . . .
H33A H 0.4516 0.0693 0.4567 0.069 Uiso 1 1 calc R . .
C45 C 0.7364(3) 0.13948(15) 1.1355(3) 0.169(5) Uani 0.50 1 d PD A 1
O1 O 0.7042(7) 0.0858(4) 1.1115(6) 0.247(10) Uani 0.50 1 d PD A 1
C45' C 0.7364(3) 0.13948(15) 1.1355(3) 0.169(5) Uani 0.50 1 d PD B 2
O1' O 0.7207(3) 0.20236(17) 1.1238(2) 0.0305(14) Uani 0.50 1 d PD B 2
O2 O 0.7579(3) 0.0910(6) 0.3670(9) 0.305(12) Uani 0.50 1 d PD C 1
C46 C 0.7151(8) 0.1369(8) 0.3815(8) 0.177(11) Uani 0.50 1 d PD C 1
O2' O 0.6388(2) 0.0786(5) 0.4057(3) 0.108(4) Uani 0.50 1 d PD D 2
C46' C 0.6973(5) 0.0499(9) 0.4295(7) 0.33(2) Uani 0.50 1 d PD D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.969(3) . ?
Cu1 N6 1.972(3) . ?
Cu1 N13 2.130(3) . ?
Cu1 Cu2 2.5099(7) . ?
Cu2 N7 1.927(3) . ?
Cu2 N3 1.933(3) . ?
Cu2 N9 2.191(4) . ?
Cu3 N11 1.954(3) . ?
Cu3 N10 1.955(3) 2_656 ?
Cu3 N5 2.082(4) 3_545 ?
Cu3 Cu3 2.5283(9) 2_656 ?
Cu4 N14 1.948(3) . ?
Cu4 N15 1.952(3) 2_656 ?
Cu4 N4 2.142(3) 4_556 ?
Cu4 Cu4 2.5027(8) 2_656 ?
N1 C5 1.311(7) . ?
N1 C1 1.337(6) . ?
N2 C6 1.323(5) . ?
N2 C3 1.403(5) . ?
N3 C6 1.327(5) . ?
N3 C9 1.390(5) . ?
N4 C7 1.343(5) . ?
N4 C11 1.351(5) . ?
N4 Cu4 2.142(3) 4_546 ?
N5 C16 1.339(5) . ?
N5 C12 1.358(5) . ?
N5 Cu3 2.082(4) 3_455 ?
N6 C17 1.325(5) . ?
N6 C14 1.405(5) . ?
N7 C17 1.305(5) . ?
N7 C20 1.392(5) . ?
N8 C22 1.316(6) . ?
N8 C18 1.358(6) . ?
N9 C27 1.289(6) . ?
N9 C23 1.340(7) . ?
N10 C28 1.312(5) . ?
N10 C25 1.394(5) . ?
N10 Cu3 1.955(3) 2_656 ?
N11 C28 1.312(5) . ?
N11 C31 1.407(5) . ?
N12 C29 1.310(7) . ?
N12 C33 1.335(7) . ?
N13 C34 1.335(5) . ?
N13 C38 1.342(5) . ?
N14 C39 1.324(4) . ?
N14 C36 1.417(4) . ?
N15 C39 1.323(4) . ?
N15 C42 1.393(4) . ?
N15 Cu4 1.952(3) 2_656 ?
N16 C40 1.312(5) . ?
N16 C44 1.324(6) . ?
C1 C2 1.362(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.392(6) . ?
C4 C5 1.370(7) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.361(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.408(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.394(5) . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.358(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.399(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.406(5) . ?
C15 C16 1.377(6) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C22 C21 1.385(6) . ?
C22 H22A 0.9300 . ?
C21 C20 1.402(6) . ?
C21 H21A 0.9300 . ?
C20 C19 1.405(6) . ?
C19 C18 1.378(6) . ?
C19 H19A 0.9300 . ?
C18 H18A 0.9300 . ?
C34 C35 1.376(5) . ?
C34 H34A 0.9300 . ?
C35 C36 1.397(5) . ?
C35 H35A 0.9300 . ?
C36 C37 1.389(5) . ?
C37 C38 1.380(5) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C39 H39A 0.9300 . ?
C44 C43 1.381(6) . ?
C44 H44A 0.9300 . ?
C43 C42 1.372(5) . ?
C43 H43A 0.9300 . ?
C42 C41 1.395(5) . ?
C41 C40 1.370(5) . ?
C41 H41A 0.9300 . ?
C40 H40A 0.9300 . ?
C27 C26 1.382(6) . ?
C27 H27A 0.9300 . ?
C26 C25 1.365(6) . ?
C26 H26A 0.9300 . ?
C25 C24 1.360(7) . ?
C24 C23 1.388(7) . ?
C24 H24A 0.9300 . ?
C23 H23A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 C30 1.392(6) . ?
C29 H29A 0.9300 . ?
C30 C31 1.381(6) . ?
C30 H30A 0.9300 . ?
C31 C32 1.380(6) . ?
C32 C33 1.346(6) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
C45 O1 1.398(2) . ?
O2 C46 1.399(2) . ?
O2' C46' 1.400(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N6 150.16(12) . . ?
N2 Cu1 N13 106.55(12) . . ?
N6 Cu1 N13 103.29(12) . . ?
N2 Cu1 Cu2 85.06(9) . . ?
N6 Cu1 Cu2 86.21(10) . . ?
N13 Cu1 Cu2 107.35(10) . . ?
N7 Cu2 N3 159.12(13) . . ?
N7 Cu2 N9 98.59(14) . . ?
N3 Cu2 N9 102.30(14) . . ?
N7 Cu2 Cu1 87.73(10) . . ?
N3 Cu2 Cu1 89.14(10) . . ?
N9 Cu2 Cu1 98.62(12) . . ?
N11 Cu3 N10 144.60(15) . 2_656 ?
N11 Cu3 N5 109.40(14) . 3_545 ?
N10 Cu3 N5 106.00(14) 2_656 3_545 ?
N11 Cu3 Cu3 87.56(10) . 2_656 ?
N10 Cu3 Cu3 85.90(10) 2_656 2_656 ?
N5 Cu3 Cu3 101.07(9) 3_545 2_656 ?
N14 Cu4 N15 154.60(14) . 2_656 ?
N14 Cu4 N4 106.01(13) . 4_556 ?
N15 Cu4 N4 99.40(13) 2_656 4_556 ?
N14 Cu4 Cu4 87.04(9) . 2_656 ?
N15 Cu4 Cu4 87.52(9) 2_656 2_656 ?
N4 Cu4 Cu4 102.55(8) 4_556 2_656 ?
C5 N1 C1 113.9(4) . . ?
C6 N2 C3 118.6(3) . . ?
C6 N2 Cu1 123.3(2) . . ?
C3 N2 Cu1 118.1(3) . . ?
C6 N3 C9 119.9(3) . . ?
C6 N3 Cu2 120.6(3) . . ?
C9 N3 Cu2 119.5(2) . . ?
C7 N4 C11 114.6(4) . . ?
C7 N4 Cu4 120.1(3) . 4_546 ?
C11 N4 Cu4 124.8(3) . 4_546 ?
C16 N5 C12 114.8(4) . . ?
C16 N5 Cu3 124.0(3) . 3_455 ?
C12 N5 Cu3 120.5(3) . 3_455 ?
C17 N6 C14 118.3(3) . . ?
C17 N6 Cu1 120.7(3) . . ?
C14 N6 Cu1 120.7(2) . . ?
C17 N7 C20 119.3(3) . . ?
C17 N7 Cu2 122.0(2) . . ?
C20 N7 Cu2 117.0(3) . . ?
C22 N8 C18 115.0(4) . . ?
C27 N9 C23 115.5(4) . . ?
C27 N9 Cu2 122.9(3) . . ?
C23 N9 Cu2 120.6(3) . . ?
C28 N10 C25 118.9(3) . . ?
C28 N10 Cu3 122.6(3) . 2_656 ?
C25 N10 Cu3 118.5(3) . 2_656 ?
C28 N11 C31 118.1(3) . . ?
C28 N11 Cu3 120.9(3) . . ?
C31 N11 Cu3 121.0(3) . . ?
C29 N12 C33 114.7(4) . . ?
C34 N13 C38 114.7(3) . . ?
C34 N13 Cu1 124.6(3) . . ?
C38 N13 Cu1 120.0(2) . . ?
C39 N14 C36 119.3(3) . . ?
C39 N14 Cu4 121.8(2) . . ?
C36 N14 Cu4 118.9(2) . . ?
C39 N15 C42 119.1(3) . . ?
C39 N15 Cu4 121.1(2) . 2_656 ?
C42 N15 Cu4 119.6(2) . 2_656 ?
C40 N16 C44 114.1(4) . . ?
N1 C1 C2 124.3(5) . . ?
N1 C1 H1A 117.9 . . ?
C2 C1 H1A 117.9 . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C2 C3 C4 114.4(4) . . ?
C2 C3 N2 118.9(3) . . ?
C4 C3 N2 126.6(4) . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 125.9(5) . . ?
N1 C5 H5A 117.0 . . ?
C4 C5 H5A 117.0 . . ?
N2 C6 N3 121.7(4) . . ?
N2 C6 H6A 119.2 . . ?
N3 C6 H6A 119.2 . . ?
N4 C7 C8 124.3(3) . . ?
N4 C7 H7A 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
N3 C9 C10 127.2(3) . . ?
N3 C9 C8 117.6(3) . . ?
C10 C9 C8 115.2(4) . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N4 C11 C10 125.2(3) . . ?
N4 C11 H11A 117.4 . . ?
C10 C11 H11A 117.4 . . ?
C13 C12 N5 124.6(4) . . ?
C13 C12 H12A 117.7 . . ?
N5 C12 H12A 117.7 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 N6 118.6(3) . . ?
C13 C14 C15 116.0(4) . . ?
N6 C14 C15 125.4(4) . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
N5 C16 C15 125.1(4) . . ?
N5 C16 H16A 117.5 . . ?
C15 C16 H16A 117.5 . . ?
N7 C17 N6 122.8(4) . . ?
N7 C17 H17A 118.6 . . ?
N6 C17 H17A 118.6 . . ?
N8 C22 C21 125.7(4) . . ?
N8 C22 H22A 117.2 . . ?
C21 C22 H22A 117.2 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
N7 C20 C21 125.5(4) . . ?
N7 C20 C19 118.5(4) . . ?
C21 C20 C19 115.6(4) . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19A 120.0 . . ?
C20 C19 H19A 120.0 . . ?
N8 C18 C19 124.3(5) . . ?
N8 C18 H18A 117.9 . . ?
C19 C18 H18A 117.9 . . ?
N13 C34 C35 125.4(4) . . ?
N13 C34 H34A 117.3 . . ?
C35 C34 H34A 117.3 . . ?
C34 C35 C36 119.1(3) . . ?
C34 C35 H35A 120.4 . . ?
C36 C35 H35A 120.4 . . ?
C37 C36 C35 116.3(3) . . ?
C37 C36 N14 117.8(3) . . ?
C35 C36 N14 125.9(3) . . ?
C38 C37 C36 119.8(4) . . ?
C38 C37 H37A 120.1 . . ?
C36 C37 H37A 120.1 . . ?
N13 C38 C37 124.6(4) . . ?
N13 C38 H38A 117.7 . . ?
C37 C38 H38A 117.7 . . ?
N15 C39 N14 122.4(3) . . ?
N15 C39 H39A 118.8 . . ?
N14 C39 H39A 118.8 . . ?
N16 C44 C43 125.0(4) . . ?
N16 C44 H44A 117.5 . . ?
C43 C44 H44A 117.5 . . ?
C42 C43 C44 120.5(4) . . ?
C42 C43 H43A 119.7 . . ?
C44 C43 H43A 119.7 . . ?
C43 C42 N15 118.4(3) . . ?
C43 C42 C41 114.6(3) . . ?
N15 C42 C41 127.0(3) . . ?
C40 C41 C42 119.9(4) . . ?
C40 C41 H41A 120.0 . . ?
C42 C41 H41A 120.0 . . ?
N16 C40 C41 125.9(4) . . ?
N16 C40 H40A 117.1 . . ?
C41 C40 H40A 117.1 . . ?
N9 C27 C26 124.0(5) . . ?
N9 C27 H27A 118.0 . . ?
C26 C27 H27A 118.0 . . ?
C25 C26 C27 121.4(4) . . ?
C25 C26 H26A 119.3 . . ?
C27 C26 H26A 119.3 . . ?
C24 C25 C26 114.7(4) . . ?
C24 C25 N10 125.1(4) . . ?
C26 C25 N10 119.9(4) . . ?
C25 C24 C23 120.7(5) . . ?
C25 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
N9 C23 C24 123.1(5) . . ?
N9 C23 H23A 118.5 . . ?
C24 C23 H23A 118.5 . . ?
N10 C28 N11 123.0(4) . . ?
N10 C28 H28A 118.5 . . ?
N11 C28 H28A 118.5 . . ?
N12 C29 C30 125.1(5) . . ?
N12 C29 H29A 117.4 . . ?
C30 C29 H29A 117.4 . . ?
C31 C30 C29 118.5(5) . . ?
C31 C30 H30A 120.7 . . ?
C29 C30 H30A 120.7 . . ?
C32 C31 C30 116.3(4) . . ?
C32 C31 N11 126.0(4) . . ?
C30 C31 N11 117.7(4) . . ?
C33 C32 C31 120.2(5) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
N12 C33 C32 125.1(5) . . ?
N12 C33 H33A 117.5 . . ?
C32 C33 H33A 117.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.330
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.124
_database_code_depnum_ccdc_archive 'CCDC 1017753'
#######################################################################
#
#                 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_2b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H48 Cu4 N16 O2'
_chemical_formula_weight         1135.18

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   C2/c

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

_cell_length_a                   20.8705(3)
_cell_length_b                   21.3742(3)
_cell_length_c                   22.7059(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.1820(10)
_cell_angle_gamma                90.00
_cell_volume                     9999.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.26

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4640
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_T_max  0.7809
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            59119
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.29
_reflns_number_total             12388
_reflns_number_gt                9234
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0574P)²+23.8944P] 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         12388
_refine_ls_number_parameters     661
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.112434(16) 0.189232(16) 0.787903(14) 0.01528(9) Uani 1 1 d . . .
Cu2 Cu 0.100067(18) 0.087883(16) 0.732040(15) 0.01752(9) Uani 1 1 d . . .
Cu3 Cu 0.544286(16) 0.021653(17) 0.717852(15) 0.01776(9) Uani 1 1 d . . .
Cu4 Cu 0.442856(16) 0.250311(16) 0.722686(14) 0.01462(9) Uani 1 1 d . . .
N1 N 0.10275(14) 0.23810(13) 1.01971(12) 0.0279(6) Uani 1 1 d . . .
N2 N 0.10087(11) 0.13868(11) 0.85774(10) 0.0143(5) Uani 1 1 d . . .
N3 N 0.09225(11) 0.04530(11) 0.80547(10) 0.0147(5) Uani 1 1 d . . .
N4 N 0.07523(12) -0.15155(11) 0.79351(10) 0.0182(5) Uani 1 1 d . . .
N5 N 0.05878(12) 0.42638(11) 0.70814(10) 0.0181(5) Uani 1 1 d . . .
N6 N 0.07728(11) 0.22944(11) 0.71106(10) 0.0153(5) Uani 1 1 d . . .
N7 N 0.07311(11) 0.13552(11) 0.66024(10) 0.0161(5) Uani 1 1 d . . .
N8 N 0.08825(17) 0.03263(14) 0.50380(12) 0.0358(7) Uani 1 1 d . . .
N9 N 0.20076(13) 0.07477(12) 0.72394(12) 0.0241(6) Uani 1 1 d . . .
N10 N 0.39832(12) 0.04885(11) 0.70975(11) 0.0180(5) Uani 1 1 d . . .
N11 N 0.48023(12) 0.05221(11) 0.65253(10) 0.0178(5) Uani 1 1 d . . .
N12 N 0.54094(16) 0.08631(13) 0.48627(12) 0.0327(7) Uani 1 1 d . . .
N13 N 0.21331(11) 0.21330(11) 0.79873(10) 0.0178(5) Uani 1 1 d . . .
N14 N 0.41551(11) 0.23282(11) 0.79916(10) 0.0133(5) Uani 1 1 d . . .
N15 N 0.52126(11) 0.22948(11) 0.84908(10) 0.0142(5) Uani 1 1 d . . .
N16 N 0.65694(13) 0.21368(13) 1.00852(11) 0.0252(6) Uani 1 1 d . . .
C1 C 0.1184(2) 0.26295(17) 0.97066(16) 0.0383(9) Uani 1 1 d . . .
H1A H 0.1305 0.3058 0.9719 0.046 Uiso 1 1 calc R . .
C2 C 0.11860(19) 0.23102(15) 0.91750(15) 0.0319(8) Uani 1 1 d . . .
H2A H 0.1308 0.2521 0.8842 0.038 Uiso 1 1 calc R . .
C3 C 0.10104(13) 0.16873(13) 0.91290(12) 0.0171(6) Uani 1 1 d . . .
C4 C 0.0822(2) 0.14279(16) 0.96348(15) 0.0393(9) Uani 1 1 d . . .
H4A H 0.0681 0.1005 0.9631 0.047 Uiso 1 1 calc R . .
C5 C 0.0841(2) 0.17853(17) 1.01433(15) 0.0427(10) Uani 1 1 d . . .
H5A H 0.0712 0.1591 1.0482 0.051 Uiso 1 1 calc R . .
C6 C 0.09455(13) 0.07696(13) 0.85601(12) 0.0154(6) Uani 1 1 d . . .
H6A H 0.0916 0.0549 0.8918 0.018 Uiso 1 1 calc R . .
C7 C 0.08948(14) -0.11508(14) 0.74923(13) 0.0192(6) Uani 1 1 d . . .
H7A H 0.0959 -0.1347 0.7131 0.023 Uiso 1 1 calc R . .
C8 C 0.09528(14) -0.05140(14) 0.75303(12) 0.0182(6) Uani 1 1 d . . .
H8A H 0.1054 -0.0284 0.7199 0.022 Uiso 1 1 calc R . .
C9 C 0.08649(13) -0.01960(13) 0.80514(12) 0.0149(5) Uani 1 1 d . . .
C10 C 0.07172(14) -0.05713(13) 0.85168(12) 0.0176(6) Uani 1 1 d . . .
H10A H 0.0651 -0.0389 0.8884 0.021 Uiso 1 1 calc R . .
C11 C 0.06696(14) -0.12132(13) 0.84347(12) 0.0184(6) Uani 1 1 d . . .
H11A H 0.0571 -0.1458 0.8758 0.022 Uiso 1 1 calc R . .
C12 C 0.09540(14) 0.39491(14) 0.75259(12) 0.0191(6) Uani 1 1 d . . .
H12A H 0.1185 0.4183 0.7847 0.023 Uiso 1 1 calc R . .
C13 C 0.10138(14) 0.33091(14) 0.75425(12) 0.0181(6) Uani 1 1 d . . .
H13A H 0.1278 0.3114 0.7871 0.022 Uiso 1 1 calc R . .
C14 C 0.06890(13) 0.29430(13) 0.70793(12) 0.0146(5) Uani 1 1 d . . .
C15 C 0.02927(13) 0.32683(14) 0.66195(12) 0.0176(6) Uani 1 1 d . . .
H15A H 0.0049 0.3046 0.6297 0.021 Uiso 1 1 calc R . .
C16 C 0.02617(14) 0.39118(14) 0.66411(12) 0.0189(6) Uani 1 1 d . . .
H16A H -0.0008 0.4121 0.6325 0.023 Uiso 1 1 calc R . .
C17 C 0.06739(13) 0.19685(13) 0.66084(12) 0.0168(6) Uani 1 1 d . . .
H17A H 0.0558 0.2184 0.6241 0.020 Uiso 1 1 calc R . .
C18 C 0.06497(18) 0.00857(16) 0.55088(14) 0.0297(8) Uani 1 1 d . . .
H18A H 0.0524 -0.0342 0.5491 0.036 Uiso 1 1 calc R . .
C19 C 0.05815(15) 0.04161(14) 0.60139(13) 0.0223(6) Uani 1 1 d . . .
H19A H 0.0416 0.0215 0.6331 0.027 Uiso 1 1 calc R . .
C20 C 0.07554(14) 0.10466(14) 0.60625(13) 0.0192(6) Uani 1 1 d . . .
C21 C 0.09937(17) 0.13061(15) 0.55764(13) 0.0264(7) Uani 1 1 d . . .
H21A H 0.1120 0.1733 0.5581 0.032 Uiso 1 1 calc R . .
C22 C 0.10437(19) 0.09342(17) 0.50869(14) 0.0339(8) Uani 1 1 d . . .
H22A H 0.1204 0.1123 0.4761 0.041 Uiso 1 1 calc R . .
C23 C 0.22804(16) 0.10493(17) 0.68240(15) 0.0301(8) Uani 1 1 d . . .
H23A H 0.2013 0.1321 0.6560 0.036 Uiso 1 1 calc R . .
C24 C 0.29201(16) 0.09930(16) 0.67534(16) 0.0310(8) Uani 1 1 d . . .
H24A H 0.3082 0.1222 0.6450 0.037 Uiso 1 1 calc R . .
C25 C 0.33292(14) 0.05977(14) 0.71301(13) 0.0192(6) Uani 1 1 d . . .
C26 C 0.30573(15) 0.03072(15) 0.75815(13) 0.0228(6) Uani 1 1 d . . .
H26A H 0.3319 0.0051 0.7865 0.027 Uiso 1 1 calc R . .
C27 C 0.24116(15) 0.03908(15) 0.76170(14) 0.0243(7) Uani 1 1 d . . .
H27A H 0.2241 0.0183 0.7928 0.029 Uiso 1 1 calc R . .
C28 C 0.41917(14) 0.06053(14) 0.65895(13) 0.0195(6) Uani 1 1 d . . .
H28A H 0.3892 0.0754 0.6260 0.023 Uiso 1 1 calc R . .
C29 C 0.58102(18) 0.08631(15) 0.53828(15) 0.0310(8) Uani 1 1 d . . .
H29A H 0.6256 0.0946 0.5375 0.037 Uiso 1 1 calc R . .
C30 C 0.56284(16) 0.07520(14) 0.59285(14) 0.0245(7) Uani 1 1 d . . .
H30A H 0.5942 0.0759 0.6281 0.029 Uiso 1 1 calc R . .
C31 C 0.49746(15) 0.06278(13) 0.59605(13) 0.0191(6) Uani 1 1 d . . .
C32 C 0.45507(16) 0.06088(14) 0.54177(13) 0.0241(7) Uani 1 1 d . . .
H32A H 0.4104 0.0514 0.5407 0.029 Uiso 1 1 calc R . .
C33 C 0.47910(18) 0.07303(15) 0.48973(14) 0.0293(7) Uani 1 1 d . . .
H33A H 0.4493 0.0719 0.4535 0.035 Uiso 1 1 calc R . .
C34 C 0.25663(14) 0.19220(15) 0.84462(13) 0.0216(6) Uani 1 1 d . . .
H34A H 0.2404 0.1724 0.8767 0.026 Uiso 1 1 calc R . .
C35 C 0.32298(14) 0.19734(14) 0.84836(13) 0.0213(6) Uani 1 1 d . . .
H35A H 0.3509 0.1812 0.8821 0.026 Uiso 1 1 calc R . .
C36 C 0.34908(13) 0.22654(13) 0.80212(12) 0.0148(5) Uani 1 1 d . . .
C37 C 0.30400(14) 0.24908(14) 0.75469(12) 0.0187(6) Uani 1 1 d . . .
H37A H 0.3186 0.2696 0.7222 0.022 Uiso 1 1 calc R . .
C38 C 0.23820(14) 0.24172(15) 0.75488(13) 0.0208(6) Uani 1 1 d . . .
H38A H 0.2089 0.2577 0.7220 0.025 Uiso 1 1 calc R . .
C39 C 0.45767(13) 0.22629(13) 0.84912(12) 0.0143(5) Uani 1 1 d . . .
H39A H 0.4421 0.2192 0.8856 0.017 Uiso 1 1 calc R . .
C40 C 0.59341(15) 0.20938(14) 1.00889(13) 0.0210(6) Uani 1 1 d . . .
H40A H 0.5799 0.2021 1.0463 0.025 Uiso 1 1 calc R . .
C41 C 0.54539(14) 0.21454(14) 0.95966(12) 0.0192(6) Uani 1 1 d . . .
H41A H 0.5009 0.2117 0.9639 0.023 Uiso 1 1 calc R . .
C42 C 0.56322(13) 0.22399(13) 0.90368(12) 0.0154(6) Uani 1 1 d . . .
C43 C 0.62988(15) 0.22897(17) 0.90290(13) 0.0263(7) Uani 1 1 d . . .
H43A H 0.6451 0.2361 0.8662 0.032 Uiso 1 1 calc R . .
C44 C 0.67395(16) 0.22361(18) 0.95501(14) 0.0305(8) Uani 1 1 d . . .
H44A H 0.7188 0.2272 0.9526 0.037 Uiso 1 1 calc R . .
O1 O 0.22647(16) 0.30920(16) 0.62450(12) 0.0603(9) Uani 1 1 d . . .
H1C H 0.2068 0.3053 0.5824 0.072 Uiso 1 1 d R A .
C45 C 0.2479(6) 0.3691(5) 0.6286(5) 0.057(3) Uani 0.50 1 d P A 1
H45A H 0.2954 0.3642 0.6305 0.068 Uiso 0.50 1 calc PR A 1
H45B H 0.2421 0.3811 0.6695 0.068 Uiso 0.50 1 calc PR A 1
C46 C 0.2348(11) 0.4260(12) 0.5962(9) 0.158(13) Uani 0.50 1 d P A 1
H46A H 0.2642 0.4587 0.6145 0.190 Uiso 0.50 1 calc PR A 1
H46B H 0.1897 0.4386 0.5968 0.190 Uiso 0.50 1 calc PR A 1
H46C H 0.2413 0.4196 0.5548 0.190 Uiso 0.50 1 calc PR A 1
C45' C 0.2112(5) 0.3776(5) 0.6364(4) 0.046(3) Uani 0.50 1 d P A 2
H45C H 0.1698 0.3763 0.6526 0.055 Uiso 0.50 1 calc PR A 2
H45D H 0.2447 0.3903 0.6702 0.055 Uiso 0.50 1 calc PR A 2
C46' C 0.2063(8) 0.4177(6) 0.6060(6) 0.080(5) Uani 0.50 1 d P A 2
H46D H 0.2007 0.4560 0.6283 0.096 Uiso 0.50 1 calc PR A 2
H46E H 0.1684 0.4117 0.5750 0.096 Uiso 0.50 1 calc PR A 2
H46F H 0.2454 0.4213 0.5874 0.096 Uiso 0.50 1 calc PR A 2
O2 O 0.1948(5) 0.3887(7) 0.8994(6) 0.172(5) Uiso 0.50 1 d PD B 1
C47 C 0.2586(5) 0.4140(8) 0.8963(6) 0.180(11) Uani 0.50 1 d PD B 1
C48 C 0.3033(6) 0.3944(8) 0.8572(6) 0.138(6) Uani 0.50 1 d PD B 1
O2' O 0.1382(4) 0.4192(4) 0.9045(3) 0.105(3) Uani 0.50 1 d PD C 2
C47' C 0.1947(4) 0.4536(5) 0.9325(6) 0.106(4) Uiso 0.50 1 d PD C 2
C48' C 0.1973(9) 0.5177(6) 0.9535(10) 0.174(9) Uiso 0.50 1 d PD C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.965(2) . ?
Cu1 N6 1.978(2) . ?
Cu1 N13 2.143(2) . ?
Cu1 Cu2 2.5027(5) . ?
Cu2 N7 1.928(2) . ?
Cu2 N3 1.929(2) . ?
Cu2 N9 2.157(3) . ?
Cu3 N11 1.944(2) . ?
Cu3 N10 1.961(2) 2_656 ?
Cu3 N5 2.076(2) 3_545 ?
Cu3 Cu3 2.5317(7) 2_656 ?
Cu4 N14 1.949(2) . ?
Cu4 N15 1.950(2) 2_656 ?
Cu4 N4 2.152(2) 4_556 ?
Cu4 Cu4 2.5067(6) 2_656 ?
N1 C1 1.321(4) . ?
N1 C5 1.331(4) . ?
N2 C6 1.326(4) . ?
N2 C3 1.407(3) . ?
N3 C6 1.326(4) . ?
N3 C9 1.392(4) . ?
N4 C11 1.340(4) . ?
N4 C7 1.343(4) . ?
N4 Cu4 2.152(2) 4_546 ?
N5 C12 1.345(4) . ?
N5 C16 1.346(4) . ?
N5 Cu3 2.076(2) 3_455 ?
N6 C17 1.324(4) . ?
N6 C14 1.398(4) . ?
N7 C17 1.317(4) . ?
N7 C20 1.400(4) . ?
N8 C22 1.342(5) . ?
N8 C18 1.345(4) . ?
N9 C27 1.341(4) . ?
N9 C23 1.342(4) . ?
N10 C28 1.320(4) . ?
N10 C25 1.398(4) . ?
N10 Cu3 1.961(2) 2_656 ?
N11 C28 1.317(4) . ?
N11 C31 1.404(4) . ?
N12 C29 1.334(5) . ?
N12 C33 1.336(5) . ?
N13 C38 1.340(4) . ?
N13 C34 1.344(4) . ?
N14 C39 1.327(3) . ?
N14 C36 1.405(3) . ?
N15 C39 1.329(3) . ?
N15 C42 1.404(3) . ?
N15 Cu4 1.950(2) 2_656 ?
N16 C40 1.330(4) . ?
N16 C44 1.336(4) . ?
C1 C2 1.387(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(4) . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.368(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.402(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.400(4) . ?
C10 C11 1.386(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.374(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.397(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.408(4) . ?
C15 C16 1.378(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.396(4) . ?
C21 C22 1.384(4) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23 C24 1.375(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.393(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.394(4) . ?
C26 C27 1.375(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?
C29 C30 1.373(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.403(4) . ?
C30 H30A 0.9500 . ?
C31 C32 1.398(4) . ?
C32 C33 1.380(4) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 C35 1.378(4) . ?
C34 H34A 0.9500 . ?
C35 C36 1.404(4) . ?
C35 H35A 0.9500 . ?
C36 C37 1.398(4) . ?
C37 C38 1.383(4) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
C39 H39A 0.9500 . ?
C40 C41 1.382(4) . ?
C40 H40A 0.9500 . ?
C41 C42 1.395(4) . ?
C41 H41A 0.9500 . ?
C42 C43 1.398(4) . ?
C43 C44 1.383(4) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?
O1 C45 1.355(10) . ?
O1 C45' 1.531(11) . ?
O1 H1C 0.9819 . ?
C45 C46 1.43(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C45' C46' 1.096(15) . ?
C45' H45C 0.9900 . ?
C45' H45D 0.9900 . ?
C46' H46D 0.9800 . ?
C46' H46E 0.9800 . ?
C46' H46F 0.9800 . ?
O2 C47 1.4499(11) . ?
C47 C48 1.4491(10) . ?
O2' C47' 1.4491(10) . ?
C47' C48' 1.4493(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N6 150.99(10) . . ?
N2 Cu1 N13 106.52(9) . . ?
N6 Cu1 N13 102.49(9) . . ?
N2 Cu1 Cu2 85.24(7) . . ?
N6 Cu1 Cu2 86.29(7) . . ?
N13 Cu1 Cu2 106.62(7) . . ?
N7 Cu2 N3 157.87(10) . . ?
N7 Cu2 N9 98.82(10) . . ?
N3 Cu2 N9 103.31(10) . . ?
N7 Cu2 Cu1 87.94(7) . . ?
N3 Cu2 Cu1 89.23(7) . . ?
N9 Cu2 Cu1 97.62(7) . . ?
N11 Cu3 N10 142.50(10) . 2_656 ?
N11 Cu3 N5 110.03(10) . 3_545 ?
N10 Cu3 N5 107.46(10) 2_656 3_545 ?
N11 Cu3 Cu3 87.90(7) . 2_656 ?
N10 Cu3 Cu3 85.48(7) 2_656 2_656 ?
N5 Cu3 Cu3 101.16(7) 3_545 2_656 ?
N14 Cu4 N15 155.07(10) . 2_656 ?
N14 Cu4 N4 105.72(9) . 4_556 ?
N15 Cu4 N4 99.21(9) 2_656 4_556 ?
N14 Cu4 Cu4 87.13(7) . 2_656 ?
N15 Cu4 Cu4 87.22(7) 2_656 2_656 ?
N4 Cu4 Cu4 102.22(7) 4_556 2_656 ?
C1 N1 C5 114.5(3) . . ?
C6 N2 C3 117.8(2) . . ?
C6 N2 Cu1 123.21(18) . . ?
C3 N2 Cu1 118.95(18) . . ?
C6 N3 C9 120.3(2) . . ?
C6 N3 Cu2 120.70(19) . . ?
C9 N3 Cu2 118.98(18) . . ?
C11 N4 C7 115.3(2) . . ?
C11 N4 Cu4 124.87(19) . 4_546 ?
C7 N4 Cu4 119.45(19) . 4_546 ?
C12 N5 C16 115.9(3) . . ?
C12 N5 Cu3 119.07(19) . 3_455 ?
C16 N5 Cu3 124.22(19) . 3_455 ?
C17 N6 C14 118.5(2) . . ?
C17 N6 Cu1 121.07(19) . . ?
C14 N6 Cu1 120.10(18) . . ?
C17 N7 C20 119.6(2) . . ?
C17 N7 Cu2 122.13(19) . . ?
C20 N7 Cu2 116.42(18) . . ?
C22 N8 C18 115.0(3) . . ?
C27 N9 C23 115.4(3) . . ?
C27 N9 Cu2 122.8(2) . . ?
C23 N9 Cu2 121.7(2) . . ?
C28 N10 C25 118.4(2) . . ?
C28 N10 Cu3 123.1(2) . 2_656 ?
C25 N10 Cu3 118.43(19) . 2_656 ?
C28 N11 C31 118.2(2) . . ?
C28 N11 Cu3 121.4(2) . . ?
C31 N11 Cu3 120.36(19) . . ?
C29 N12 C33 115.0(3) . . ?
C38 N13 C34 115.8(2) . . ?
C38 N13 Cu1 120.93(19) . . ?
C34 N13 Cu1 122.38(19) . . ?
C39 N14 C36 118.3(2) . . ?
C39 N14 Cu4 122.22(18) . . ?
C36 N14 Cu4 119.50(18) . . ?
C39 N15 C42 118.5(2) . . ?
C39 N15 Cu4 121.93(18) . 2_656 ?
C42 N15 Cu4 119.23(18) . 2_656 ?
C40 N16 C44 115.3(3) . . ?
N1 C1 C2 124.8(3) . . ?
N1 C1 H1A 117.6 . . ?
C2 C1 H1A 117.6 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 115.4(3) . . ?
C2 C3 N2 118.1(3) . . ?
C4 C3 N2 126.4(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 125.1(3) . . ?
N1 C5 H5A 117.4 . . ?
C4 C5 H5A 117.4 . . ?
N2 C6 N3 121.5(2) . . ?
N2 C6 H6A 119.2 . . ?
N3 C6 H6A 119.2 . . ?
N4 C7 C8 123.9(3) . . ?
N4 C7 H7A 118.0 . . ?
C8 C7 H7A 118.0 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
N3 C9 C10 126.6(2) . . ?
N3 C9 C8 117.7(2) . . ?
C10 C9 C8 115.7(3) . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
N4 C11 C10 125.1(3) . . ?
N4 C11 H11A 117.5 . . ?
C10 C11 H11A 117.5 . . ?
N5 C12 C13 123.8(3) . . ?
N5 C12 H12A 118.1 . . ?
C13 C12 H12A 118.1 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 N6 118.4(2) . . ?
C13 C14 C15 116.0(3) . . ?
N6 C14 C15 125.6(3) . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
N5 C16 C15 124.3(3) . . ?
N5 C16 H16A 117.9 . . ?
C15 C16 H16A 117.9 . . ?
N7 C17 N6 122.1(3) . . ?
N7 C17 H17A 119.0 . . ?
N6 C17 H17A 119.0 . . ?
N8 C18 C19 124.5(3) . . ?
N8 C18 H18A 117.8 . . ?
C19 C18 H18A 117.8 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C19 C20 C21 116.2(3) . . ?
C19 C20 N7 118.6(3) . . ?
C21 C20 N7 124.9(3) . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
N8 C22 C21 124.9(3) . . ?
N8 C22 H22A 117.5 . . ?
C21 C22 H22A 117.5 . . ?
N9 C23 C24 124.7(3) . . ?
N9 C23 H23A 117.7 . . ?
C24 C23 H23A 117.7 . . ?
C23 C24 C25 119.5(3) . . ?
C23 C24 H24A 120.2 . . ?
C25 C24 H24A 120.2 . . ?
C24 C25 C26 116.1(3) . . ?
C24 C25 N10 125.2(3) . . ?
C26 C25 N10 118.7(3) . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
N9 C27 C26 124.0(3) . . ?
N9 C27 H27A 118.0 . . ?
C26 C27 H27A 118.0 . . ?
N11 C28 N10 122.0(3) . . ?
N11 C28 H28A 119.0 . . ?
N10 C28 H28A 119.0 . . ?
N12 C29 C30 125.1(3) . . ?
N12 C29 H29A 117.5 . . ?
C30 C29 H29A 117.5 . . ?
C29 C30 C31 119.4(3) . . ?
C29 C30 H30A 120.3 . . ?
C31 C30 H30A 120.3 . . ?
C32 C31 C30 116.3(3) . . ?
C32 C31 N11 125.6(3) . . ?
C30 C31 N11 118.1(3) . . ?
C33 C32 C31 118.9(3) . . ?
C33 C32 H32A 120.5 . . ?
C31 C32 H32A 120.5 . . ?
N12 C33 C32 125.2(3) . . ?
N12 C33 H33A 117.4 . . ?
C32 C33 H33A 117.4 . . ?
N13 C34 C35 124.5(3) . . ?
N13 C34 H34A 117.8 . . ?
C35 C34 H34A 117.8 . . ?
C34 C35 C36 119.7(3) . . ?
C34 C35 H35A 120.2 . . ?
C36 C35 H35A 120.2 . . ?
C37 C36 C35 115.8(3) . . ?
C37 C36 N14 118.6(2) . . ?
C35 C36 N14 125.6(3) . . ?
C38 C37 C36 120.3(3) . . ?
C38 C37 H37A 119.8 . . ?
C36 C37 H37A 119.8 . . ?
N13 C38 C37 123.8(3) . . ?
N13 C38 H38A 118.1 . . ?
C37 C38 H38A 118.1 . . ?
N14 C39 N15 121.3(2) . . ?
N14 C39 H39A 119.3 . . ?
N15 C39 H39A 119.3 . . ?
N16 C40 C41 125.7(3) . . ?
N16 C40 H40A 117.1 . . ?
C41 C40 H40A 117.1 . . ?
C40 C41 C42 119.0(3) . . ?
C40 C41 H41A 120.5 . . ?
C42 C41 H41A 120.5 . . ?
C41 C42 C43 115.7(3) . . ?
C41 C42 N15 126.7(3) . . ?
C43 C42 N15 117.7(2) . . ?
C44 C43 C42 120.7(3) . . ?
C44 C43 H43A 119.7 . . ?
C42 C43 H43A 119.7 . . ?
N16 C44 C43 123.7(3) . . ?
N16 C44 H44A 118.2 . . ?
C43 C44 H44A 118.2 . . ?
C45 O1 C45' 32.9(6) . . ?
C45 O1 H1C 103.3 . . ?
C45' O1 H1C 100.8 . . ?
O1 C45 C46 137.4(11) . . ?
O1 C45 H45A 102.8 . . ?
C46 C45 H45A 102.8 . . ?
O1 C45 H45B 102.8 . . ?
C46 C45 H45B 102.8 . . ?
H45A C45 H45B 105.0 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C46' C45' O1 129.5(9) . . ?
C46' C45' H45C 104.9 . . ?
O1 C45' H45C 104.9 . . ?
C46' C45' H45D 104.9 . . ?
O1 C45' H45D 104.9 . . ?
H45C C45' H45D 105.8 . . ?
C45' C46' H46D 109.5 . . ?
C45' C46' H46E 109.5 . . ?
H46D C46' H46E 109.5 . . ?
C45' C46' H46F 109.5 . . ?
H46D C46' H46F 109.5 . . ?
H46E C46' H46F 109.5 . . ?
C48 C47 O2 127.46(15) . . ?
O2' C47' C48' 127.55(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.650
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 1017754'
#######################################################################
#
#                 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_2c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H52 Cu4 N16 O2'
_chemical_formula_weight         1187.26

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   C2/c

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

_cell_length_a                   21.0123(5)
_cell_length_b                   21.4061(5)
_cell_length_c                   22.6642(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.4950(10)
_cell_angle_gamma                90.00
_cell_volume                     10054.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.23

_exptl_crystal_description       PLATE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4864
_exptl_absorpt_coefficient_mu    1.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5447
_exptl_absorpt_correction_T_max  0.6718
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42360
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         26.00
_reflns_number_total             9872
_reflns_number_gt                6876
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0772P)²+70.7563P] 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         9872
_refine_ls_number_parameters     614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11445(3) 0.19060(3) 0.78724(3) 0.01689(17) Uani 1 1 d . . .
Cu2 Cu 0.10387(3) 0.08905(3) 0.73168(3) 0.01835(18) Uani 1 1 d . . .
Cu3 Cu 0.54363(3) 0.02167(3) 0.71713(3) 0.01845(18) Uani 1 1 d . . .
Cu4 Cu 0.44320(3) 0.25245(3) 0.72297(3) 0.01576(17) Uani 1 1 d . . .
N1 N 0.0979(2) 0.2409(2) 1.0176(2) 0.0266(12) Uani 1 1 d . . .
N2 N 0.1013(2) 0.1403(2) 0.85686(18) 0.0171(10) Uani 1 1 d . . .
N3 N 0.0936(2) 0.04716(19) 0.80508(18) 0.0156(9) Uani 1 1 d . . .
N4 N 0.0751(2) -0.1494(2) 0.79263(19) 0.0177(10) Uani 1 1 d . . .
N5 N 0.0570(2) 0.4265(2) 0.70703(19) 0.0184(10) Uani 1 1 d . . .
N6 N 0.0784(2) 0.23001(19) 0.70983(19) 0.0158(9) Uani 1 1 d . . .
N7 N 0.0755(2) 0.1361(2) 0.65924(19) 0.0175(10) Uani 1 1 d . . .
N8 N 0.0866(3) 0.0348(3) 0.5016(2) 0.0424(15) Uani 1 1 d . . .
N9 N 0.2028(2) 0.0767(2) 0.7243(2) 0.0246(11) Uani 1 1 d . . .
N10 N 0.3989(2) 0.0502(2) 0.7107(2) 0.0177(10) Uani 1 1 d . . .
N11 N 0.4792(2) 0.05266(19) 0.65233(19) 0.0177(10) Uani 1 1 d . . .
N12 N 0.5326(2) 0.0885(2) 0.4834(2) 0.0256(11) Uani 1 1 d . . .
N13 N 0.2153(2) 0.2152(2) 0.7991(2) 0.0195(10) Uani 1 1 d . . .
N14 N 0.4158(2) 0.23466(19) 0.79940(19) 0.0148(9) Uani 1 1 d . . .
N15 N 0.5213(2) 0.23098(19) 0.84860(19) 0.0150(9) Uani 1 1 d . . .
N16 N 0.6594(2) 0.2159(2) 1.0076(2) 0.0258(11) Uani 1 1 d . . .
C1 C 0.1206(3) 0.2638(3) 0.9707(3) 0.0308(15) Uani 1 1 d . . .
H1A H 0.1364 0.3045 0.9736 0.037 Uiso 1 1 calc R . .
C2 C 0.1226(3) 0.2320(3) 0.9184(3) 0.0262(13) Uani 1 1 d . . .
H2A H 0.1389 0.2513 0.8873 0.031 Uiso 1 1 calc R . .
C3 C 0.1002(3) 0.1710(2) 0.9120(2) 0.0178(11) Uani 1 1 d . . .
C4 C 0.0747(3) 0.1472(3) 0.9598(2) 0.0288(14) Uani 1 1 d . . .
H4A H 0.0571 0.1072 0.9577 0.035 Uiso 1 1 calc R . .
C5 C 0.0752(3) 0.1827(3) 1.0105(3) 0.0352(16) Uani 1 1 d . . .
H5A H 0.0585 0.1649 1.0421 0.042 Uiso 1 1 calc R . .
C6 C 0.0947(2) 0.0790(2) 0.8551(2) 0.0161(11) Uani 1 1 d . . .
H6A H 0.0908 0.0576 0.8901 0.019 Uiso 1 1 calc R . .
C7 C 0.0919(3) -0.1135(2) 0.7493(2) 0.0188(12) Uani 1 1 d . . .
H7A H 0.0996 -0.1329 0.7145 0.023 Uiso 1 1 calc R . .
C8 C 0.0984(3) -0.0497(2) 0.7530(2) 0.0196(12) Uani 1 1 d . . .
H8A H 0.1102 -0.0275 0.7212 0.024 Uiso 1 1 calc R . .
C9 C 0.0871(2) -0.0177(2) 0.8046(2) 0.0152(11) Uani 1 1 d . . .
C10 C 0.0703(3) -0.0552(2) 0.8498(2) 0.0193(12) Uani 1 1 d . . .
H10A H 0.0636 -0.0373 0.8857 0.023 Uiso 1 1 calc R . .
C11 C 0.0636(3) -0.1190(2) 0.8412(2) 0.0208(12) Uani 1 1 d . . .
H11A H 0.0501 -0.1424 0.8715 0.025 Uiso 1 1 calc R . .
C12 C 0.0925(3) 0.3951(2) 0.7523(2) 0.0197(12) Uani 1 1 d . . .
H12A H 0.1138 0.4181 0.7844 0.024 Uiso 1 1 calc R . .
C13 C 0.0993(3) 0.3314(2) 0.7543(2) 0.0190(12) Uani 1 1 d . . .
H13A H 0.1243 0.3124 0.7871 0.023 Uiso 1 1 calc R . .
C14 C 0.0685(3) 0.2948(2) 0.7067(2) 0.0172(11) Uani 1 1 d . . .
C15 C 0.0300(3) 0.3269(2) 0.6603(2) 0.0194(12) Uani 1 1 d . . .
H15A H 0.0072 0.3050 0.6282 0.023 Uiso 1 1 calc R . .
C16 C 0.0259(3) 0.3916(3) 0.6624(2) 0.0199(12) Uani 1 1 d . . .
H16A H 0.0000 0.4119 0.6310 0.024 Uiso 1 1 calc R . .
C17 C 0.0688(3) 0.1974(2) 0.6599(2) 0.0180(12) Uani 1 1 d . . .
H17A H 0.0569 0.2183 0.6238 0.022 Uiso 1 1 calc R . .
C22 C 0.1023(4) 0.0945(3) 0.5072(3) 0.0387(17) Uani 1 1 d . . .
H22A H 0.1170 0.1132 0.4749 0.046 Uiso 1 1 calc R . .
C21 C 0.0991(3) 0.1317(3) 0.5560(2) 0.0290(14) Uani 1 1 d . . .
H21A H 0.1114 0.1734 0.5563 0.035 Uiso 1 1 calc R . .
C20 C 0.0769(3) 0.1052(3) 0.6054(2) 0.0221(12) Uani 1 1 d . . .
C19 C 0.0609(3) 0.0419(3) 0.6005(2) 0.0250(13) Uani 1 1 d . . .
H19A H 0.0468 0.0215 0.6322 0.030 Uiso 1 1 calc R . .
C18 C 0.0660(3) 0.0100(3) 0.5498(3) 0.0346(16) Uani 1 1 d . . .
H18A H 0.0543 -0.0319 0.5481 0.042 Uiso 1 1 calc R . .
C34 C 0.2585(3) 0.1935(2) 0.8441(2) 0.0200(12) Uani 1 1 d . . .
H34A H 0.2427 0.1735 0.8751 0.024 Uiso 1 1 calc R . .
C35 C 0.3248(3) 0.1984(2) 0.8486(2) 0.0194(12) Uani 1 1 d . . .
H35A H 0.3520 0.1823 0.8816 0.023 Uiso 1 1 calc R . .
C36 C 0.3502(3) 0.2282(2) 0.8022(2) 0.0166(11) Uani 1 1 d . . .
C37 C 0.3049(3) 0.2520(3) 0.7558(2) 0.0207(12) Uani 1 1 d . . .
H37A H 0.3189 0.2733 0.7245 0.025 Uiso 1 1 calc R . .
C38 C 0.2400(3) 0.2444(3) 0.7555(2) 0.0222(13) Uani 1 1 d . . .
H38A H 0.2115 0.2605 0.7233 0.027 Uiso 1 1 calc R . .
C39 C 0.4582(2) 0.2275(2) 0.8486(2) 0.0139(11) Uani 1 1 d . . .
H39A H 0.4436 0.2199 0.8845 0.017 Uiso 1 1 calc R . .
C44 C 0.6748(3) 0.2276(3) 0.9535(3) 0.0311(15) Uani 1 1 d . . .
H44A H 0.7180 0.2329 0.9506 0.037 Uiso 1 1 calc R . .
C43 C 0.6297(3) 0.2322(3) 0.9020(3) 0.0261(13) Uani 1 1 d . . .
H43A H 0.6434 0.2401 0.8658 0.031 Uiso 1 1 calc R . .
C42 C 0.5643(3) 0.2252(2) 0.9033(2) 0.0166(11) Uani 1 1 d . . .
C41 C 0.5487(3) 0.2130(2) 0.9592(2) 0.0205(12) Uani 1 1 d . . .
H41A H 0.5058 0.2078 0.9638 0.025 Uiso 1 1 calc R . .
C40 C 0.5967(3) 0.2088(2) 1.0078(2) 0.0202(12) Uani 1 1 d . . .
H40A H 0.5842 0.2001 1.0444 0.024 Uiso 1 1 calc R . .
C27 C 0.2437(3) 0.0421(3) 0.7629(2) 0.0236(13) Uani 1 1 d . . .
H27A H 0.2273 0.0224 0.7937 0.028 Uiso 1 1 calc R . .
C26 C 0.3073(3) 0.0339(3) 0.7599(2) 0.0216(12) Uani 1 1 d . . .
H26A H 0.3330 0.0099 0.7887 0.026 Uiso 1 1 calc R . .
C25 C 0.3341(3) 0.0615(2) 0.7139(2) 0.0188(12) Uani 1 1 d . . .
C24 C 0.2929(3) 0.1001(3) 0.6757(3) 0.0301(14) Uani 1 1 d . . .
H24A H 0.3085 0.1221 0.6457 0.036 Uiso 1 1 calc R . .
C23 C 0.2292(3) 0.1058(3) 0.6823(3) 0.0298(14) Uani 1 1 d . . .
H23A H 0.2028 0.1315 0.6556 0.036 Uiso 1 1 calc R . .
C28 C 0.4189(3) 0.0622(2) 0.6596(2) 0.0184(12) Uani 1 1 d . . .
H28A H 0.3897 0.0778 0.6277 0.022 Uiso 1 1 calc R . .
C29 C 0.5740(3) 0.0904(2) 0.5351(3) 0.0255(13) Uani 1 1 d . . .
H29A H 0.6168 0.1006 0.5336 0.031 Uiso 1 1 calc R . .
C30 C 0.5577(3) 0.0785(2) 0.5900(2) 0.0197(12) Uani 1 1 d . . .
H30A H 0.5890 0.0805 0.6242 0.024 Uiso 1 1 calc R . .
C31 C 0.4945(3) 0.0634(2) 0.5950(2) 0.0174(12) Uani 1 1 d . . .
C32 C 0.4517(3) 0.0587(2) 0.5417(2) 0.0218(12) Uani 1 1 d . . .
H32A H 0.4092 0.0465 0.5418 0.026 Uiso 1 1 calc R . .
C33 C 0.4725(2) 0.07224(18) 0.48798(17) 0.0250(13) Uani 1 1 d . . .
H33A H 0.4425 0.0698 0.4530 0.030 Uiso 1 1 calc R . .
O1 O 0.3262(2) -0.04882(18) 0.88264(17) 0.1125(17) Uiso 1 1 d R . .
C45 C 0.2966(2) -0.10578(18) 0.86074(17) 0.1125(17) Uiso 1 1 d R . .
H45A H 0.3280 -0.1394 0.8664 0.135 Uiso 1 1 calc R . .
H45B H 0.2800 -0.1022 0.8183 0.135 Uiso 1 1 calc R . .
C46 C 0.2456(2) -0.11851(18) 0.89292(17) 0.1125(17) Uiso 1 1 d R . .
H46A H 0.2529 -0.1581 0.9137 0.135 Uiso 1 1 calc R . .
H46B H 0.2049 -0.1209 0.8656 0.135 Uiso 1 1 calc R . .
C47 C 0.2435(2) -0.06942(18) 0.93471(17) 0.1125(17) Uiso 1 1 d R . .
H47A H 0.2019 -0.0487 0.9270 0.135 Uiso 1 1 calc R . .
H47B H 0.2499 -0.0860 0.9751 0.135 Uiso 1 1 calc R . .
C48 C 0.2934(2) -0.02635(18) 0.92836(17) 0.1125(17) Uiso 1 1 d R . .
H48A H 0.3231 -0.0227 0.9657 0.135 Uiso 1 1 calc R . .
H48B H 0.2751 0.0146 0.9177 0.135 Uiso 1 1 calc R . .
O2 O 0.1890(4) 0.4305(4) 0.9146(4) 0.115(2) Uiso 1 1 d . . .
C49 C 0.1945(14) 0.3701(13) 0.8835(12) 0.115(2) Uiso 0.50 1 d P A 1
C50 C 0.2534(15) 0.3642(14) 0.8704(13) 0.115(2) Uiso 0.50 1 d P A 1
C51 C 0.2927(15) 0.4300(14) 0.8841(13) 0.115(2) Uiso 0.50 1 d P A 1
C52 C 0.2621(14) 0.4567(13) 0.9354(12) 0.115(2) Uiso 0.50 1 d P A 1
C49' C 0.2114(13) 0.4001(13) 0.9664(12) 0.115(2) Uiso 0.50 1 d P A 2
H49C H 0.2079 0.4267 1.0004 0.138 Uiso 0.50 1 calc PR A 2
H49D H 0.1862 0.3626 0.9695 0.138 Uiso 0.50 1 calc PR A 2
C50' C 0.2673(13) 0.3865(13) 0.9663(12) 0.115(2) Uiso 0.50 1 d P A 2
H50C H 0.2747 0.3452 0.9838 0.138 Uiso 0.50 1 calc PR A 2
H50D H 0.2940 0.4155 0.9924 0.138 Uiso 0.50 1 calc PR A 2
C51' C 0.2908(14) 0.3862(15) 0.9058(12) 0.115(2) Uiso 0.50 1 d P A 2
H51C H 0.3321 0.4073 0.9087 0.138 Uiso 0.50 1 calc PR A 2
H51D H 0.2952 0.3439 0.8919 0.138 Uiso 0.50 1 calc PR A 2
C52' C 0.2452(15) 0.4170(15) 0.8691(12) 0.115(2) Uiso 0.50 1 d P A 2
H52C H 0.2275 0.3917 0.8348 0.138 Uiso 0.50 1 calc PR A 2
H52D H 0.2616 0.4558 0.8554 0.138 Uiso 0.50 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.967(4) . ?
Cu1 N6 1.981(4) . ?
Cu1 N13 2.157(4) . ?
Cu1 Cu2 2.5035(9) . ?
Cu2 N3 1.933(4) . ?
Cu2 N7 1.935(4) . ?
Cu2 N9 2.129(5) . ?
Cu3 N11 1.943(4) . ?
Cu3 N10 1.964(4) 2_656 ?
Cu3 N5 2.075(4) 3_545 ?
Cu3 Cu3 2.5463(12) 2_656 ?
Cu4 N15 1.949(4) 2_656 ?
Cu4 N14 1.951(4) . ?
Cu4 N4 2.155(4) 4_556 ?
Cu4 Cu4 2.4968(13) 2_656 ?
N1 C1 1.327(7) . ?
N1 C5 1.334(7) . ?
N2 C6 1.321(7) . ?
N2 C3 1.416(7) . ?
N3 C6 1.320(6) . ?
N3 C9 1.396(6) . ?
N4 C11 1.335(7) . ?
N4 C7 1.340(6) . ?
N4 Cu4 2.155(4) 4_546 ?
N5 C16 1.338(7) . ?
N5 C12 1.345(7) . ?
N5 Cu3 2.075(4) 3_455 ?
N6 C17 1.317(7) . ?
N6 C14 1.403(7) . ?
N7 C17 1.319(7) . ?
N7 C20 1.393(7) . ?
N8 C22 1.320(8) . ?
N8 C18 1.350(8) . ?
N9 C23 1.333(7) . ?
N9 C27 1.341(7) . ?
N10 C28 1.322(7) . ?
N10 C25 1.397(7) . ?
N10 Cu3 1.964(4) 2_656 ?
N11 C28 1.319(7) . ?
N11 C31 1.408(6) . ?
N12 C33 1.331(6) . ?
N12 C29 1.341(8) . ?
N13 C34 1.331(7) . ?
N13 C38 1.344(7) . ?
N14 C39 1.317(6) . ?
N14 C36 1.397(7) . ?
N15 C39 1.328(6) . ?
N15 C42 1.413(7) . ?
N15 Cu4 1.949(4) 2_656 ?
N16 C40 1.326(7) . ?
N16 C44 1.342(7) . ?
C1 C2 1.375(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.387(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(7) . ?
C4 C5 1.377(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.408(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.392(7) . ?
C10 C11 1.385(7) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.401(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.396(8) . ?
C15 C16 1.389(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C22 C21 1.375(8) . ?
C22 H22A 0.9300 . ?
C21 C20 1.401(8) . ?
C21 H21A 0.9300 . ?
C20 C19 1.396(8) . ?
C19 C18 1.356(8) . ?
C19 H19A 0.9300 . ?
C18 H18A 0.9300 . ?
C34 C35 1.384(7) . ?
C34 H34A 0.9300 . ?
C35 C36 1.408(7) . ?
C35 H35A 0.9300 . ?
C36 C37 1.393(7) . ?
C37 C38 1.373(8) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C39 H39A 0.9300 . ?
C44 C43 1.379(8) . ?
C44 H44A 0.9300 . ?
C43 C42 1.387(8) . ?
C43 H43A 0.9300 . ?
C42 C41 1.385(7) . ?
C41 C40 1.368(8) . ?
C41 H41A 0.9300 . ?
C40 H40A 0.9300 . ?
C27 C26 1.361(8) . ?
C27 H27A 0.9300 . ?
C26 C25 1.395(7) . ?
C26 H26A 0.9300 . ?
C25 C24 1.391(8) . ?
C24 C23 1.377(8) . ?
C24 H24A 0.9300 . ?
C23 H23A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 C30 1.369(8) . ?
C29 H29A 0.9300 . ?
C30 C31 1.388(7) . ?
C30 H30A 0.9300 . ?
C31 C32 1.387(8) . ?
C32 C33 1.390(7) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
O1 C48 1.4200 . ?
O1 C45 1.4200 . ?
C45 C46 1.4200 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.4200 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.4200 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
O2 C49' 1.36(2) . ?
O2 C49 1.49(3) . ?
O2 C52 1.63(3) . ?
O2 C52' 1.72(3) . ?
C49 C50 1.33(4) . ?
C50 C51 1.64(4) . ?
C51 C52 1.53(4) . ?
C49' C50' 1.21(3) . ?
C49' H49C 0.9700 . ?
C49' H49D 0.9700 . ?
C50' C51' 1.53(3) . ?
C50' H50C 0.9700 . ?
C50' H50D 0.9700 . ?
C51' C52' 1.33(3) . ?
C51' H51C 0.9700 . ?
C51' H51D 0.9700 . ?
C52' H52C 0.9700 . ?
C52' H52D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N6 149.29(18) . . ?
N2 Cu1 N13 107.40(17) . . ?
N6 Cu1 N13 103.31(17) . . ?
N2 Cu1 Cu2 85.17(13) . . ?
N6 Cu1 Cu2 86.28(13) . . ?
N13 Cu1 Cu2 106.15(13) . . ?
N3 Cu2 N7 155.42(19) . . ?
N3 Cu2 N9 104.97(18) . . ?
N7 Cu2 N9 99.61(18) . . ?
N3 Cu2 Cu1 89.04(13) . . ?
N7 Cu2 Cu1 87.94(13) . . ?
N9 Cu2 Cu1 98.05(13) . . ?
N11 Cu3 N10 141.25(18) . 2_656 ?
N11 Cu3 N5 110.01(18) . 3_545 ?
N10 Cu3 N5 108.73(18) 2_656 3_545 ?
N11 Cu3 Cu3 87.88(13) . 2_656 ?
N10 Cu3 Cu3 85.19(13) 2_656 2_656 ?
N5 Cu3 Cu3 100.85(12) 3_545 2_656 ?
N15 Cu4 N14 154.51(17) 2_656 . ?
N15 Cu4 N4 100.12(17) 2_656 4_556 ?
N14 Cu4 N4 105.37(17) . 4_556 ?
N15 Cu4 Cu4 86.69(13) 2_656 2_656 ?
N14 Cu4 Cu4 87.87(13) . 2_656 ?
N4 Cu4 Cu4 102.16(12) 4_556 2_656 ?
C1 N1 C5 114.6(5) . . ?
C6 N2 C3 118.1(4) . . ?
C6 N2 Cu1 123.2(3) . . ?
C3 N2 Cu1 118.7(3) . . ?
C6 N3 C9 120.5(4) . . ?
C6 N3 Cu2 120.8(3) . . ?
C9 N3 Cu2 118.7(3) . . ?
C11 N4 C7 115.5(4) . . ?
C11 N4 Cu4 123.9(4) . 4_546 ?
C7 N4 Cu4 120.1(3) . 4_546 ?
C16 N5 C12 116.0(5) . . ?
C16 N5 Cu3 125.0(4) . 3_455 ?
C12 N5 Cu3 118.4(4) . 3_455 ?
C17 N6 C14 118.8(4) . . ?
C17 N6 Cu1 121.1(4) . . ?
C14 N6 Cu1 119.9(3) . . ?
C17 N7 C20 120.0(4) . . ?
C17 N7 Cu2 121.7(4) . . ?
C20 N7 Cu2 116.6(3) . . ?
C22 N8 C18 114.3(5) . . ?
C23 N9 C27 115.2(5) . . ?
C23 N9 Cu2 121.6(4) . . ?
C27 N9 Cu2 123.1(4) . . ?
C28 N10 C25 117.9(5) . . ?
C28 N10 Cu3 123.3(4) . 2_656 ?
C25 N10 Cu3 118.8(3) . 2_656 ?
C28 N11 C31 117.4(5) . . ?
C28 N11 Cu3 121.5(4) . . ?
C31 N11 Cu3 121.1(4) . . ?
C33 N12 C29 115.2(5) . . ?
C34 N13 C38 115.4(5) . . ?
C34 N13 Cu1 122.7(3) . . ?
C38 N13 Cu1 120.8(4) . . ?
C39 N14 C36 119.0(4) . . ?
C39 N14 Cu4 121.1(3) . . ?
C36 N14 Cu4 119.9(3) . . ?
C39 N15 C42 119.2(4) . . ?
C39 N15 Cu4 122.2(4) . 2_656 ?
C42 N15 Cu4 118.3(3) . 2_656 ?
C40 N16 C44 114.4(5) . . ?
N1 C1 C2 125.0(5) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 115.8(5) . . ?
C4 C3 N2 125.8(5) . . ?
C2 C3 N2 118.2(5) . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 124.8(6) . . ?
N1 C5 H5A 117.6 . . ?
C4 C5 H5A 117.6 . . ?
N3 C6 N2 121.7(5) . . ?
N3 C6 H6A 119.2 . . ?
N2 C6 H6A 119.2 . . ?
N4 C7 C8 124.2(5) . . ?
N4 C7 H7A 117.9 . . ?
C8 C7 H7A 117.9 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 N3 127.1(5) . . ?
C10 C9 C8 115.5(5) . . ?
N3 C9 C8 117.4(4) . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
N4 C11 C10 124.6(5) . . ?
N4 C11 H11A 117.7 . . ?
C10 C11 H11A 117.7 . . ?
N5 C12 C13 124.3(5) . . ?
N5 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 116.2(5) . . ?
C15 C14 N6 125.9(5) . . ?
C13 C14 N6 117.9(5) . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
N5 C16 C15 123.8(5) . . ?
N5 C16 H16A 118.1 . . ?
C15 C16 H16A 118.1 . . ?
N6 C17 N7 122.4(5) . . ?
N6 C17 H17A 118.8 . . ?
N7 C17 H17A 118.8 . . ?
N8 C22 C21 126.4(6) . . ?
N8 C22 H22A 116.8 . . ?
C21 C22 H22A 116.8 . . ?
C22 C21 C20 118.5(6) . . ?
C22 C21 H21A 120.8 . . ?
C20 C21 H21A 120.8 . . ?
N7 C20 C19 119.3(5) . . ?
N7 C20 C21 124.5(5) . . ?
C19 C20 C21 115.9(5) . . ?
C18 C19 C20 120.3(6) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
N8 C18 C19 124.7(6) . . ?
N8 C18 H18A 117.7 . . ?
C19 C18 H18A 117.7 . . ?
N13 C34 C35 125.4(5) . . ?
N13 C34 H34A 117.3 . . ?
C35 C34 H34A 117.3 . . ?
C34 C35 C36 118.7(5) . . ?
C34 C35 H35A 120.6 . . ?
C36 C35 H35A 120.6 . . ?
C37 C36 N14 119.0(5) . . ?
C37 C36 C35 115.7(5) . . ?
N14 C36 C35 125.3(5) . . ?
C38 C37 C36 121.0(5) . . ?
C38 C37 H37A 119.5 . . ?
C36 C37 H37A 119.5 . . ?
N13 C38 C37 123.7(5) . . ?
N13 C38 H38A 118.1 . . ?
C37 C38 H38A 118.1 . . ?
N14 C39 N15 122.0(5) . . ?
N14 C39 H39A 119.0 . . ?
N15 C39 H39A 119.0 . . ?
N16 C44 C43 123.4(5) . . ?
N16 C44 H44A 118.3 . . ?
C43 C44 H44A 118.3 . . ?
C44 C43 C42 121.3(5) . . ?
C44 C43 H43A 119.3 . . ?
C42 C43 H43A 119.3 . . ?
C41 C42 C43 115.0(5) . . ?
C41 C42 N15 127.3(5) . . ?
C43 C42 N15 117.7(5) . . ?
C40 C41 C42 119.6(5) . . ?
C40 C41 H41A 120.2 . . ?
C42 C41 H41A 120.2 . . ?
N16 C40 C41 126.2(5) . . ?
N16 C40 H40A 116.9 . . ?
C41 C40 H40A 116.9 . . ?
N9 C27 C26 124.6(5) . . ?
N9 C27 H27A 117.7 . . ?
C26 C27 H27A 117.7 . . ?
C27 C26 C25 120.1(5) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C24 C25 C26 115.6(5) . . ?
C24 C25 N10 125.6(5) . . ?
C26 C25 N10 118.9(5) . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
N9 C23 C24 124.2(6) . . ?
N9 C23 H23A 117.9 . . ?
C24 C23 H23A 117.9 . . ?
N11 C28 N10 122.1(5) . . ?
N11 C28 H28A 119.0 . . ?
N10 C28 H28A 119.0 . . ?
N12 C29 C30 124.5(6) . . ?
N12 C29 H29A 117.8 . . ?
C30 C29 H29A 117.8 . . ?
C29 C30 C31 120.2(5) . . ?
C29 C30 H30A 119.9 . . ?
C31 C30 H30A 119.9 . . ?
C32 C31 C30 116.0(5) . . ?
C32 C31 N11 125.3(5) . . ?
C30 C31 N11 118.7(5) . . ?
C31 C32 C33 119.7(5) . . ?
C31 C32 H32A 120.2 . . ?
C33 C32 H32A 120.2 . . ?
N12 C33 C32 124.3(4) . . ?
N12 C33 H33A 117.9 . . ?
C32 C33 H33A 117.9 . . ?
C48 O1 C45 108.0 . . ?
O1 C45 C46 108.0 . . ?
O1 C45 H45A 110.1 . . ?
C46 C45 H45A 110.1 . . ?
O1 C45 H45B 110.1 . . ?
C46 C45 H45B 110.1 . . ?
H45A C45 H45B 108.4 . . ?
C45 C46 C47 108.0 . . ?
C45 C46 H46A 110.1 . . ?
C47 C46 H46A 110.1 . . ?
C45 C46 H46B 110.1 . . ?
C47 C46 H46B 110.1 . . ?
H46A C46 H46B 108.4 . . ?
C48 C47 C46 108.0 . . ?
C48 C47 H47A 110.1 . . ?
C46 C47 H47A 110.1 . . ?
C48 C47 H47B 110.1 . . ?
C46 C47 H47B 110.1 . . ?
H47A C47 H47B 108.4 . . ?
C47 C48 O1 108.0 . . ?
C47 C48 H48A 110.1 . . ?
O1 C48 H48A 110.1 . . ?
C47 C48 H48B 110.1 . . ?
O1 C48 H48B 110.1 . . ?
H48A C48 H48B 108.4 . . ?
C49' O2 C49 87.2(16) . . ?
C49' O2 C52 74.9(16) . . ?
C49 O2 C52 107.0(16) . . ?
C49' O2 C52' 105.4(16) . . ?
C49 O2 C52' 56.8(15) . . ?
C52 O2 C52' 61.5(14) . . ?
C50 C49 O2 110(2) . . ?
C49 C50 C51 110(3) . . ?
C52 C51 C50 102(2) . . ?
C51 C52 O2 98.5(19) . . ?
C50' C49' O2 108(3) . . ?
C50' C49' H49C 110.1 . . ?
O2 C49' H49C 110.1 . . ?
C50' C49' H49D 110.1 . . ?
O2 C49' H49D 110.1 . . ?
H49C C49' H49D 108.4 . . ?
C49' C50' C51' 117(3) . . ?
C49' C50' H50C 108.0 . . ?
C51' C50' H50C 108.0 . . ?
C49' C50' H50D 108.0 . . ?
C51' C50' H50D 108.0 . . ?
H50C C50' H50D 107.2 . . ?
C52' C51' C50' 105(2) . . ?
C52' C51' H51C 110.8 . . ?
C50' C51' H51C 110.8 . . ?
C52' C51' H51D 110.8 . . ?
C50' C51' H51D 110.8 . . ?
H51C C51' H51D 108.9 . . ?
C51' C52' O2 102(2) . . ?
C51' C52' H52C 111.4 . . ?
O2 C52' H52C 111.4 . . ?
C51' C52' H52D 111.4 . . ?
O2 C52' H52D 111.4 . . ?
H52C C52' H52D 109.3 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.466
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.131
_database_code_depnum_ccdc_archive 'CCDC 1017755'
#######################################################################
#
#                 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_3a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 B Cu3 F4 N8 O3'
_chemical_formula_weight         753.97

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   16.2527(9)
_cell_length_b                   12.3588(8)
_cell_length_c                   17.4471(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.657(3)
_cell_angle_gamma                90.00
_cell_volume                     3185.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8381
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.13

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26573
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6255
_reflns_number_gt                4116
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1197P)²+5.3310P] 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         6255
_refine_ls_number_parameters     410
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.2090
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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 0.38111(4) 0.39912(6) 0.12487(4) 0.0243(2) Uani 1 1 d . . .
Cu2 Cu 0.46858(4) 0.33072(6) 0.04226(4) 0.0238(2) Uani 1 1 d . . .
Cu3 Cu -0.0759(4) 0.3838(6) 0.0714(3) 0.0473(10) Uani 0.70 1 d P . 1
Cu3' Cu -0.0886(10) 0.3675(14) 0.0467(7) 0.051(2) Uani 0.30 1 d P . 2
N1 N 0.0289(4) 0.3746(6) 0.0495(4) 0.0447(15) Uani 1 1 d . . .
N2 N 0.2741(3) 0.3636(4) 0.0218(3) 0.0256(11) Uani 1 1 d . . .
N3 N 0.3545(3) 0.3073(4) -0.0531(3) 0.0239(11) Uani 1 1 d . . .
N4 N 0.3699(3) 0.1890(4) -0.2735(3) 0.0271(12) Uani 1 1 d . . .
N5 N 0.5042(4) 0.6928(4) 0.3801(3) 0.0351(13) Uani 1 1 d . . .
N6 N 0.4901(3) 0.4877(4) 0.1825(3) 0.0259(11) Uani 1 1 d . . .
N7 N 0.5696(3) 0.4225(4) 0.1082(3) 0.0243(11) Uani 1 1 d . . .
N8 N 0.8135(4) 0.3916(5) 0.0806(4) 0.0467(17) Uani 1 1 d . . .
C1 C 0.0974(5) 0.4408(7) 0.0909(5) 0.0451(19) Uani 1 1 d . . .
H1A H 0.0908 0.4908 0.1278 0.054 Uiso 1 1 calc R . .
C2 C 0.1780(4) 0.4392(6) 0.0820(4) 0.0315(15) Uani 1 1 d . . .
H2A H 0.2248 0.4859 0.1137 0.038 Uiso 1 1 calc R . .
C3 C 0.1891(4) 0.3668(6) 0.0248(4) 0.0302(15) Uani 1 1 d . . .
C4 C 0.1172(5) 0.3029(7) -0.0188(4) 0.049(2) Uani 1 1 d . . .
H4A H 0.1204 0.2542 -0.0580 0.058 Uiso 1 1 calc R . .
C5 C 0.0381(5) 0.3088(8) -0.0059(5) 0.056(2) Uani 1 1 d . . .
H5A H -0.0103 0.2644 -0.0378 0.067 Uiso 1 1 calc R . .
C6 C 0.2769(4) 0.3241(5) -0.0482(3) 0.0246(13) Uani 1 1 d . . .
H6A H 0.2231 0.3081 -0.0943 0.030 Uiso 1 1 calc R . .
C7 C 0.4374(4) 0.1809(5) -0.1970(4) 0.0285(14) Uani 1 1 d . . .
H7A H 0.4905 0.1473 -0.1923 0.034 Uiso 1 1 calc R . .
C8 C 0.4336(4) 0.2193(5) -0.1242(4) 0.0255(13) Uani 1 1 d . . .
H8A H 0.4836 0.2126 -0.0727 0.031 Uiso 1 1 calc R . .
C9 C 0.3544(4) 0.2683(5) -0.1283(3) 0.0228(12) Uani 1 1 d . . .
C10 C 0.2854(4) 0.2828(5) -0.2091(4) 0.0274(14) Uani 1 1 d . . .
H10A H 0.2329 0.3201 -0.2164 0.033 Uiso 1 1 calc R . .
C11 C 0.2959(4) 0.2414(5) -0.2779(4) 0.0256(13) Uani 1 1 d . . .
H11A H 0.2485 0.2505 -0.3308 0.031 Uiso 1 1 calc R . .
C12 C 0.4297(4) 0.6836(6) 0.3083(4) 0.0377(17) Uani 1 1 d . . .
H12A H 0.3796 0.7249 0.3024 0.045 Uiso 1 1 calc R . .
C13 C 0.4225(4) 0.6171(5) 0.2428(4) 0.0310(15) Uani 1 1 d . . .
H13A H 0.3688 0.6143 0.1941 0.037 Uiso 1 1 calc R . .
C14 C 0.4966(4) 0.5535(5) 0.2501(4) 0.0252(13) Uani 1 1 d . . .
C15 C 0.5735(4) 0.5592(5) 0.3260(4) 0.0308(14) Uani 1 1 d . . .
H15A H 0.6239 0.5169 0.3346 0.037 Uiso 1 1 calc R . .
C16 C 0.5739(4) 0.6281(5) 0.3880(4) 0.0342(15) Uani 1 1 d . . .
H16A H 0.6255 0.6302 0.4385 0.041 Uiso 1 1 calc R . .
C17 C 0.5640(4) 0.4821(5) 0.1689(4) 0.0231(13) Uani 1 1 d . . .
H17A H 0.6144 0.5219 0.2036 0.028 Uiso 1 1 calc R . .
C18 C 0.7318(5) 0.3707(7) 0.0171(5) 0.0460(19) Uani 1 1 d . . .
H18A H 0.7295 0.3472 -0.0344 0.055 Uiso 1 1 calc R . .
C19 C 0.6516(4) 0.3832(5) 0.0259(4) 0.0326(15) Uani 1 1 d . . .
H19A H 0.5968 0.3688 -0.0196 0.039 Uiso 1 1 calc R . .
C20 C 0.6525(4) 0.4169(5) 0.1017(4) 0.0289(14) Uani 1 1 d . . .
C21 C 0.7366(4) 0.4347(6) 0.1677(4) 0.0359(16) Uani 1 1 d . . .
H21A H 0.7406 0.4543 0.2206 0.043 Uiso 1 1 calc R . .
C22 C 0.8137(5) 0.4232(6) 0.1547(5) 0.0465(19) Uani 1 1 d . . .
H22A H 0.8691 0.4380 0.1993 0.056 Uiso 1 1 calc R . .
F4 F 0.7972(6) 0.2030(7) 0.3609(6) 0.085(3) Uani 0.628(8) 1 d PD A 1
F3 F 0.8424(6) 0.3122(9) 0.4702(5) 0.095(4) Uani 0.628(8) 1 d PD A 1
F2 F 0.8636(8) 0.3521(12) 0.3546(8) 0.147(5) Uani 0.628(8) 1 d PD A 1
F1 F 0.7243(7) 0.3535(11) 0.3546(9) 0.130(5) Uani 0.628(8) 1 d PD A 1
B B 0.8073(6) 0.3077(7) 0.3851(5) 0.110(8) Uani 0.628(8) 1 d PDU A 1
B' B 0.824(2) 0.490(2) 0.4306(11) 0.16(2) Uiso 0.372(8) 1 d PD A 2
F1' F 0.884(2) 0.414(2) 0.4756(19) 0.181(11) Uiso 0.372(8) 1 d PD A 2
F2' F 0.848(2) 0.564(2) 0.387(2) 0.239(16) Uiso 0.372(8) 1 d PD A 2
F3' F 0.792(2) 0.519(3) 0.4877(19) 0.226(15) Uiso 0.372(8) 1 d PD A 2
F4' F 0.7700(14) 0.4192(16) 0.3727(12) 0.102(6) Uiso 0.372(8) 1 d PD A 2
C24 C 0.8098(13) 0.547(2) 0.626(2) 0.81(5) Uiso 0.50 1 d PD B 1
O1 O 0.9530(13) 0.5438(16) 0.7162(15) 0.187(10) Uiso 0.50 1 d PD B 1
C23 C 0.8804(16) 0.6149(15) 0.677(2) 0.185(16) Uiso 0.50 1 d PD B 1
O1' O 0.8098(13) 0.547(2) 0.626(2) 0.81(5) Uiso 0.50 1 d PD C 2
C23' C 0.748(3) 0.478(3) 0.638(2) 0.26(2) Uiso 0.50 1 d PD C 2
C24' C 0.723(2) 0.405(2) 0.570(2) 0.142(11) Uiso 0.50 1 d PD C 2
O3 O 0.1174(12) 0.6486(15) 0.2405(11) 0.123(8) Uiso 0.521(17) 1 d P D 1
O3' O 0.9653(18) 0.574(2) 0.3631(17) 0.180(12) Uiso 0.479(17) 1 d P D 2
O2' O 0.9696(19) 0.7245(16) 0.7509(17) 0.188(11) Uiso 0.521(17) 1 d PD D 1
O2 O 0.969(2) 0.806(3) 0.748(2) 0.205(13) Uiso 0.479(17) 1 d P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.960(5) . ?
Cu1 N6 1.965(5) . ?
Cu1 N4 2.153(5) 4_566 ?
Cu1 Cu2 2.5540(9) . ?
Cu2 N3 1.927(5) . ?
Cu2 N7 1.932(5) . ?
Cu2 N5 2.107(5) 2_645 ?
Cu3 N8 1.873(8) 1_455 ?
Cu3 N1 1.899(9) . ?
Cu3' N1 1.893(16) . ?
Cu3' N8 1.938(16) 1_455 ?
N1 C5 1.318(10) . ?
N1 C1 1.326(9) . ?
N2 C6 1.333(7) . ?
N2 C3 1.406(7) . ?
N3 C6 1.316(7) . ?
N3 C9 1.397(7) . ?
N4 C7 1.331(7) . ?
N4 C11 1.340(7) . ?
N4 Cu1 2.153(5) 4_565 ?
N5 C12 1.335(8) . ?
N5 C16 1.345(8) . ?
N5 Cu2 2.107(5) 2_655 ?
N6 C17 1.318(7) . ?
N6 C14 1.401(7) . ?
N7 C17 1.324(8) . ?
N7 C20 1.399(7) . ?
N8 C22 1.348(9) . ?
N8 C18 1.353(9) . ?
N8 Cu3 1.873(8) 1_655 ?
N8 Cu3' 1.938(16) 1_655 ?
C1 C2 1.383(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.407(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.351(9) . ?
C4 C5 1.396(9) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.381(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.398(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.399(8) . ?
C10 C11 1.379(8) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.372(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.399(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.393(8) . ?
C15 C16 1.375(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.383(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.382(9) . ?
C19 H19A 0.9300 . ?
C20 C21 1.389(9) . ?
C21 C22 1.370(9) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
F4 B 1.350(2) . ?
F3 B 1.351(2) . ?
F2 B 1.351(2) . ?
F1 B 1.350(2) . ?
B' F4' 1.350(2) . ?
B' F2' 1.350(2) . ?
B' F3' 1.350(2) . ?
B' F1' 1.351(2) . ?
C24 C23 1.4002(11) . ?
O1 C23 1.3999(10) . ?
C23' C24' 1.4000(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N6 149.2(2) . . ?
N2 Cu1 N4 107.18(19) . 4_566 ?
N6 Cu1 N4 103.22(19) . 4_566 ?
N2 Cu1 Cu2 84.12(13) . . ?
N6 Cu1 Cu2 82.97(14) . . ?
N4 Cu1 Cu2 123.78(14) 4_566 . ?
N3 Cu2 N7 151.0(2) . . ?
N3 Cu2 N5 107.6(2) . 2_645 ?
N7 Cu2 N5 101.2(2) . 2_645 ?
N3 Cu2 Cu1 88.59(14) . . ?
N7 Cu2 Cu1 90.25(14) . . ?
N5 Cu2 Cu1 85.51(16) 2_645 . ?
N8 Cu3 N1 173.9(4) 1_455 . ?
N1 Cu3' N8 159.0(7) . 1_455 ?
C5 N1 C1 117.0(6) . . ?
C5 N1 Cu3' 112.0(6) . . ?
C1 N1 Cu3' 130.6(6) . . ?
C5 N1 Cu3 124.8(5) . . ?
C1 N1 Cu3 118.2(5) . . ?
Cu3' N1 Cu3 13.4(4) . . ?
C6 N2 C3 117.0(5) . . ?
C6 N2 Cu1 124.5(4) . . ?
C3 N2 Cu1 118.0(4) . . ?
C6 N3 C9 119.3(5) . . ?
C6 N3 Cu2 121.6(4) . . ?
C9 N3 Cu2 119.1(4) . . ?
C7 N4 C11 116.0(5) . . ?
C7 N4 Cu1 118.0(4) . 4_565 ?
C11 N4 Cu1 125.4(4) . 4_565 ?
C12 N5 C16 116.2(5) . . ?
C12 N5 Cu2 122.5(4) . 2_655 ?
C16 N5 Cu2 118.2(4) . 2_655 ?
C17 N6 C14 115.3(5) . . ?
C17 N6 Cu1 125.0(4) . . ?
C14 N6 Cu1 119.3(4) . . ?
C17 N7 C20 118.8(5) . . ?
C17 N7 Cu2 118.5(4) . . ?
C20 N7 Cu2 122.0(4) . . ?
C22 N8 C18 116.8(6) . . ?
C22 N8 Cu3 118.5(5) . 1_655 ?
C18 N8 Cu3 124.7(5) . 1_655 ?
C22 N8 Cu3' 131.5(6) . 1_655 ?
C18 N8 Cu3' 111.7(6) . 1_655 ?
Cu3 N8 Cu3' 13.2(4) 1_655 1_655 ?
N1 C1 C2 123.3(7) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 N2 126.6(6) . . ?
C4 C3 C2 115.7(6) . . ?
N2 C3 C2 117.5(5) . . ?
C3 C4 C5 121.2(7) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
N1 C5 C4 122.9(7) . . ?
N1 C5 H5A 118.5 . . ?
C4 C5 H5A 118.5 . . ?
N3 C6 N2 121.1(5) . . ?
N3 C6 H6A 119.4 . . ?
N2 C6 H6A 119.4 . . ?
N4 C7 C8 124.2(5) . . ?
N4 C7 H7A 117.9 . . ?
C8 C7 H7A 117.9 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
N3 C9 C8 117.5(5) . . ?
N3 C9 C10 126.1(5) . . ?
C8 C9 C10 116.2(5) . . ?
C11 C10 C9 119.4(5) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N4 C11 C10 124.3(5) . . ?
N4 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
N5 C12 C13 124.1(6) . . ?
N5 C12 H12A 117.9 . . ?
C13 C12 H12A 117.9 . . ?
C12 C13 C14 119.3(6) . . ?
C12 C13 H13A 120.4 . . ?
C14 C13 H13A 120.4 . . ?
C15 C14 C13 117.1(6) . . ?
C15 C14 N6 123.5(5) . . ?
C13 C14 N6 119.4(5) . . ?
C16 C15 C14 119.1(6) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
N5 C16 C15 124.0(6) . . ?
N5 C16 H16A 118.0 . . ?
C15 C16 H16A 118.0 . . ?
N6 C17 N7 123.0(5) . . ?
N6 C17 H17A 118.5 . . ?
N7 C17 H17A 118.5 . . ?
N8 C18 C19 122.4(7) . . ?
N8 C18 H18A 118.8 . . ?
C19 C18 H18A 118.8 . . ?
C20 C19 C18 120.4(6) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 117.0(5) . . ?
C19 C20 N7 117.9(6) . . ?
C21 C20 N7 125.0(6) . . ?
C22 C21 C20 119.9(6) . . ?
C22 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
N8 C22 C21 123.4(6) . . ?
N8 C22 H22A 118.3 . . ?
C21 C22 H22A 118.3 . . ?
F1 B F4 107.9(10) . . ?
F1 B F3 108.0(9) . . ?
F4 B F3 108.9(10) . . ?
F1 B F2 113.8(11) . . ?
F4 B F2 106.3(10) . . ?
F3 B F2 111.8(10) . . ?
F4' B' F2' 105.54(18) . . ?
F4' B' F3' 113(3) . . ?
F2' B' F3' 122(3) . . ?
F4' B' F1' 94(2) . . ?
F2' B' F1' 119(3) . . ?
F3' B' F1' 100(2) . . ?
O1 C23 C24 103.57(10) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.143
_database_code_depnum_ccdc_archive 'CCDC 1017756'
#######################################################################
#
#                 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_3b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Cl Cu3 N8 O5'
_chemical_formula_weight         730.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   16.2717(2)
_cell_length_b                   12.6684(2)
_cell_length_c                   17.6021(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.5230(10)
_cell_angle_gamma                90.00
_cell_volume                     3351.68(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.33

_exptl_crystal_description       PLATE
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    2.008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5005
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32180
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.33
_reflns_number_total             8300
_reflns_number_gt                6238
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0975P)²+1.2766P] 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         8300
_refine_ls_number_parameters     417
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.525280(19) 0.17199(3) 0.450940(18) 0.03306(9) Uani 1 1 d . . .
Cu2 Cu 0.61366(2) 0.10409(3) 0.367080(19) 0.03422(9) Uani 1 1 d . . .
Cu3 Cu 0.08008(3) 0.11289(5) 0.44143(3) 0.07014(16) Uani 1 1 d . . .
Cl Cl 0.19156(13) 0.2931(2) 0.62728(16) 0.0867(8) Uani 0.640(4) 1 d PD A 1
O1 O 0.1540(4) 0.2939(6) 0.5395(4) 0.130(4) Uani 0.640(4) 1 d PD A 1
O2 O 0.2728(4) 0.3480(6) 0.6554(5) 0.118(3) Uani 0.640(4) 1 d PD A 1
O3 O 0.1289(4) 0.3408(6) 0.6557(4) 0.122(3) Uani 0.640(4) 1 d PD A 1
O4 O 0.2032(5) 0.1867(5) 0.6474(6) 0.151(3) Uani 0.640(4) 1 d PD A 1
Cl' Cl 0.2026(5) 0.3351(7) 0.6123(4) 0.172(4) Uani 0.360(4) 1 d PD A 2
O1' O 0.1481(11) 0.3024(14) 0.5322(8) 0.179(10) Uani 0.360(4) 1 d PD A 2
O2' O 0.2006(11) 0.4491(11) 0.6186(12) 0.321(14) Uani 0.360(4) 1 d PD A 2
O3' O 0.2949(9) 0.3060(14) 0.6310(11) 0.258(16) Uani 0.360(4) 1 d PD A 2
O4' O 0.1744(13) 0.2873(19) 0.6724(11) 0.36(3) Uani 0.360(4) 1 d PD A 2
N1 N 0.18722(16) 0.0997(2) 0.42550(18) 0.0514(7) Uani 1 1 d . . .
N2 N 0.42786(13) 0.07895(18) 0.39037(13) 0.0309(5) Uani 1 1 d . . .
N3 N 0.50737(13) 0.01550(18) 0.31539(13) 0.0315(5) Uani 1 1 d . . .
N4 N 0.49599(17) -0.1948(2) 0.12662(15) 0.0441(6) Uani 1 1 d . . .
N5 N 0.62327(16) 0.3129(2) 0.76267(14) 0.0402(6) Uani 1 1 d . . .
N6 N 0.63614(13) 0.19378(18) 0.54330(12) 0.0291(5) Uani 1 1 d . . .
N7 N 0.71772(13) 0.1400(2) 0.46713(13) 0.0325(5) Uani 1 1 d . . .
N8 N 0.96771(17) 0.1193(3) 0.44932(18) 0.0594(8) Uani 1 1 d . . .
C1 C 0.2665(2) 0.1190(3) 0.4854(2) 0.0523(8) Uani 1 1 d . . .
H1A H 0.2677 0.1388 0.5367 0.063 Uiso 1 1 calc R . .
C2 C 0.34598(19) 0.1113(3) 0.47570(18) 0.0432(7) Uani 1 1 d . . .
H2A H 0.3990 0.1259 0.5196 0.052 Uiso 1 1 calc R . .
C3 C 0.34728(16) 0.0815(2) 0.40006(15) 0.0317(6) Uani 1 1 d . . .
C4 C 0.26441(18) 0.0614(3) 0.33711(19) 0.0458(7) Uani 1 1 d . . .
H4A H 0.2610 0.0419 0.2851 0.055 Uiso 1 1 calc R . .
C5 C 0.1886(2) 0.0706(3) 0.3527(2) 0.0553(9) Uani 1 1 d . . .
H5A H 0.1345 0.0558 0.3101 0.066 Uiso 1 1 calc R . .
C6 C 0.43456(16) 0.0197(2) 0.33138(16) 0.0319(5) Uani 1 1 d . . .
H6A H 0.3859 -0.0210 0.2997 0.038 Uiso 1 1 calc R . .
C7 C 0.5680(2) -0.1872(3) 0.19635(19) 0.0480(8) Uani 1 1 d . . .
H7A H 0.6161 -0.2313 0.2033 0.058 Uiso 1 1 calc R . .
C8 C 0.57451(18) -0.1171(3) 0.25867(18) 0.0421(7) Uani 1 1 d . . .
H8A H 0.6265 -0.1134 0.3056 0.051 Uiso 1 1 calc R . .
C9 C 0.50264(17) -0.0523(2) 0.25057(16) 0.0321(5) Uani 1 1 d . . .
C10 C 0.42806(19) -0.0591(2) 0.17683(18) 0.0401(7) Uani 1 1 d . . .
H10A H 0.3790 -0.0159 0.1678 0.048 Uiso 1 1 calc R . .
C11 C 0.4279(2) -0.1303(3) 0.11785(19) 0.0441(7) Uani 1 1 d . . .
H11A H 0.3778 -0.1338 0.0692 0.053 Uiso 1 1 calc R . .
C12 C 0.55639(19) 0.3192(3) 0.68995(17) 0.0423(7) Uani 1 1 d . . .
H12A H 0.5042 0.3517 0.6874 0.051 Uiso 1 1 calc R . .
C13 C 0.55963(18) 0.2804(3) 0.61776(16) 0.0387(6) Uani 1 1 d . . .
H13A H 0.5105 0.2878 0.5687 0.046 Uiso 1 1 calc R . .
C14 C 0.63553(16) 0.2307(2) 0.61806(14) 0.0295(5) Uani 1 1 d . . .
C15 C 0.70551(18) 0.2204(2) 0.69493(15) 0.0375(6) Uani 1 1 d . . .
H15A H 0.7578 0.1861 0.6998 0.045 Uiso 1 1 calc R . .
C16 C 0.69561(19) 0.2621(3) 0.76330(16) 0.0411(7) Uani 1 1 d . . .
H16A H 0.7428 0.2543 0.8137 0.049 Uiso 1 1 calc R . .
C17 C 0.71255(17) 0.1774(2) 0.53589(15) 0.0326(6) Uani 1 1 d . . .
H17A H 0.7650 0.1925 0.5804 0.039 Uiso 1 1 calc R . .
C18 C 0.9002(2) 0.0591(3) 0.4061(2) 0.0532(8) Uani 1 1 d . . .
H18A H 0.9085 0.0107 0.3699 0.064 Uiso 1 1 calc R . .
C19 C 0.81767(18) 0.0635(3) 0.41124(18) 0.0434(7) Uani 1 1 d . . .
H19A H 0.7724 0.0189 0.3789 0.052 Uiso 1 1 calc R . .
C20 C 0.80200(17) 0.1345(3) 0.46462(16) 0.0382(6) Uani 1 1 d . . .
C21 C 0.8727(2) 0.1994(4) 0.5091(2) 0.0724(12) Uani 1 1 d . . .
H21A H 0.8658 0.2507 0.5440 0.087 Uiso 1 1 calc R . .
C22 C 0.9537(2) 0.1875(4) 0.5014(3) 0.0831(15) Uani 1 1 d . . .
H22A H 1.0010 0.2292 0.5342 0.100 Uiso 1 1 calc R . .
C23 C 0.9856(2) 0.13436(17) 0.7766(5) 0.31(3) Uiso 0.25 1 d PD . .
C23' C 1.0237(2) 0.15220(17) 0.7350(4) 0.185(16) Uiso 0.25 1 d PD . .
C24 C 1.0345(7) 0.0444(3) 0.7649(7) 0.258(13) Uiso 0.50 1 d PD . .
O5 O 0.9803(7) 0.2397(3) 0.7510(7) 0.259(8) Uiso 0.50 1 d PD . .
C25 C 0.7049(14) -0.0867(3) 0.0650(4) 0.199(9) Uiso 0.50 1 d PD . .
C26 C 0.73300(18) -0.0189(6) 0.1368(4) 0.225(10) Uiso 0.50 1 d PD . .
O6 O 0.7951(10) 0.0440(18) 0.1205(15) 0.410(16) Uiso 0.50 1 d PD . .


_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 N6 1.930(2) . ?
Cu1 N2 1.935(2) . ?
Cu1 N4 2.114(2) 2_655 ?
Cu1 Cu2 2.5716(4) . ?
Cu2 N3 1.968(2) . ?
Cu2 N7 1.973(2) . ?
Cu2 N5 2.174(2) 4_565 ?
Cu3 N1 1.876(2) . ?
Cu3 N8 1.888(3) 1_455 ?
Cl O4 1.389(7) . ?
Cl O2 1.405(6) . ?
Cl O1 1.427(7) . ?
Cl O3 1.431(6) . ?
Cl' O1' 1.410(13) . ?
Cl' O4' 1.438(14) . ?
Cl' O2' 1.451(14) . ?
Cl' O3' 1.457(14) . ?
N1 C1 1.339(4) . ?
N1 C5 1.342(5) . ?
N2 C6 1.320(3) . ?
N2 C3 1.386(3) . ?
N3 C6 1.319(3) . ?
N3 C9 1.406(3) . ?
N4 C11 1.337(4) . ?
N4 C7 1.337(4) . ?
N4 Cu1 2.114(2) 2_645 ?
N5 C12 1.327(4) . ?
N5 C16 1.338(4) . ?
N5 Cu2 2.174(2) 4_566 ?
N6 C17 1.315(3) . ?
N6 C14 1.400(3) . ?
N7 C17 1.332(3) . ?
N7 C20 1.391(3) . ?
N8 C18 1.313(5) . ?
N8 C22 1.342(5) . ?
N8 Cu3 1.888(3) 1_655 ?
C1 C2 1.372(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.392(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.402(4) . ?
C4 C5 1.368(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.383(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.391(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.399(4) . ?
C10 C11 1.375(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.401(3) . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.393(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.387(5) . ?
C21 C22 1.383(5) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C23' 1.150(11) . ?
C23 O5 1.4000(10) . ?
C23 C24 1.4500(10) . ?
C23' O5 1.4000(10) . ?
C23' C24 1.4499(10) . ?
C25 C26 1.4499(10) . ?
C26 O6 1.3999(10) . ?

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
N6 Cu1 N2 148.78(10) . . ?
N6 Cu1 N4 107.38(10) . 2_655 ?
N2 Cu1 N4 103.50(9) . 2_655 ?
N6 Cu1 Cu2 89.06(6) . . ?
N2 Cu1 Cu2 90.01(6) . . ?
N4 Cu1 Cu2 83.43(8) 2_655 . ?
N3 Cu2 N7 147.80(9) . . ?
N3 Cu2 N5 102.71(9) . 4_565 ?
N7 Cu2 N5 109.14(9) . 4_565 ?
N3 Cu2 Cu1 82.56(6) . . ?
N7 Cu2 Cu1 83.56(6) . . ?
N5 Cu2 Cu1 124.09(7) 4_565 . ?
N1 Cu3 N8 175.16(14) . 1_455 ?
O4 Cl O2 111.9(5) . . ?
O4 Cl O1 104.1(5) . . ?
O2 Cl O1 109.4(5) . . ?
O4 Cl O3 111.5(5) . . ?
O2 Cl O3 111.6(4) . . ?
O1 Cl O3 108.0(4) . . ?
O1' Cl' O4' 110.9(9) . . ?
O1' Cl' O2' 110.2(9) . . ?
O4' Cl' O2' 109.9(10) . . ?
O1' Cl' O3' 110.5(9) . . ?
O4' Cl' O3' 108.7(9) . . ?
O2' Cl' O3' 106.6(9) . . ?
C1 N1 C5 116.1(3) . . ?
C1 N1 Cu3 122.4(2) . . ?
C5 N1 Cu3 121.5(2) . . ?
C6 N2 C3 118.5(2) . . ?
C6 N2 Cu1 118.89(17) . . ?
C3 N2 Cu1 122.16(18) . . ?
C6 N3 C9 115.0(2) . . ?
C6 N3 Cu2 125.49(18) . . ?
C9 N3 Cu2 119.25(16) . . ?
C11 N4 C7 117.3(3) . . ?
C11 N4 Cu1 119.3(2) . 2_645 ?
C7 N4 Cu1 121.3(2) . 2_645 ?
C12 N5 C16 115.5(2) . . ?
C12 N5 Cu2 119.22(19) . 4_566 ?
C16 N5 Cu2 125.00(18) . 4_566 ?
C17 N6 C14 119.5(2) . . ?
C17 N6 Cu1 120.52(17) . . ?
C14 N6 Cu1 119.90(16) . . ?
C17 N7 C20 116.9(2) . . ?
C17 N7 Cu2 124.19(17) . . ?
C20 N7 Cu2 118.66(17) . . ?
C18 N8 C22 116.5(3) . . ?
C18 N8 Cu3 123.4(2) . 1_655 ?
C22 N8 Cu3 120.1(3) . 1_655 ?
N1 C1 C2 123.9(3) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
N2 C3 C2 119.1(2) . . ?
N2 C3 C4 124.6(2) . . ?
C2 C3 C4 116.3(2) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 H5A 117.9 . . ?
C4 C5 H5A 117.9 . . ?
N3 C6 N2 122.8(2) . . ?
N3 C6 H6A 118.6 . . ?
N2 C6 H6A 118.6 . . ?
N4 C7 C8 123.2(3) . . ?
N4 C7 H7A 118.4 . . ?
C8 C7 H7A 118.4 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C8 C9 C10 117.0(2) . . ?
C8 C9 N3 119.7(2) . . ?
C10 C9 N3 123.3(2) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N4 C11 C10 123.5(3) . . ?
N4 C11 H11A 118.2 . . ?
C10 C11 H11A 118.2 . . ?
N5 C12 C13 124.0(3) . . ?
N5 C12 H12A 118.0 . . ?
C13 C12 H12A 118.0 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 N6 118.4(2) . . ?
C13 C14 C15 116.1(2) . . ?
N6 C14 C15 125.5(2) . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
N5 C16 C15 125.0(2) . . ?
N5 C16 H16A 117.5 . . ?
C15 C16 H16A 117.5 . . ?
N6 C17 N7 122.5(2) . . ?
N6 C17 H17A 118.8 . . ?
N7 C17 H17A 118.8 . . ?
N8 C18 C19 123.8(3) . . ?
N8 C18 H18A 118.1 . . ?
C19 C18 H18A 118.1 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C21 C20 N7 124.6(3) . . ?
C21 C20 C19 115.9(3) . . ?
N7 C20 C19 119.4(3) . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
N8 C22 C21 123.7(4) . . ?
N8 C22 H22A 118.2 . . ?
C21 C22 H22A 118.2 . . ?
C23' C23 O5 65.7(3) . . ?
C23' C23 C24 66.6(2) . . ?
O5 C23 C24 132.3(5) . . ?
C23 C23' O5 65.8(3) . . ?
C23 C23' C24 66.6(2) . . ?
O5 C23' C24 132.3(5) . . ?
C23' C24 C23 46.7(5) . . ?
C23' O5 C23 48.5(5) . . ?
O6 C26 C25 99.8(14) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.124





_database_code_depnum_ccdc_archive 'CCDC 1017757'
