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

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#
#                 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H40 Cu2 N2 O8'
_chemical_formula_weight         1092.06

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           Tetragonal
_symmetry_space_group_name_H-M   P4/nnc

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

_cell_length_a                   16.589(2)
_cell_length_b                   16.589(2)
_cell_length_c                   9.584(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2637.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    1152
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      21.32

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_T_max  0.9261
_exptl_absorpt_process_details   
;
SADABS; sheldrick, 1996
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13444
_diffrn_reflns_av_R_equivalents  0.1282
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1178
_reflns_number_gt                755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0991P)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         1178
_refine_ls_number_parameters     91
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      1.807
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6422(4) 0.6422(4) 0.2500 0.021(2) Uani 1 2 d S . .
C2 C 0.5793(4) 0.5793(4) 0.2500 0.022(2) Uani 1 2 d S . .
C3 C 0.5123(5) 0.5870(5) 0.1602(8) 0.0247(19) Uani 1 1 d . . .
C4 C 0.5008(5) 0.6550(5) 0.0706(8) 0.029(2) Uani 1 1 d . . .
H4 H 0.5388 0.6978 0.0719 0.035 Uiso 1 1 calc R . .
C5 C 0.4363(5) 0.6592(5) -0.0161(8) 0.030(2) Uani 1 1 d . . .
H5 H 0.4300 0.7049 -0.0748 0.036 Uiso 1 1 calc R . .
C6 C 0.3785(5) 0.5969(5) -0.0207(8) 0.033(2) Uani 1 1 d . . .
H6 H 0.3345 0.6000 -0.0839 0.039 Uiso 1 1 calc R . .
C7 C 0.3858(5) 0.5325(5) 0.0654(9) 0.032(2) Uani 1 1 d . . .
H7 H 0.3462 0.4911 0.0628 0.039 Uiso 1 1 calc R . .
C8 C 0.4520(5) 0.5257(5) 0.1599(8) 0.027(2) Uani 1 1 d . . .
C9 C 0.4643(4) 0.4643(4) 0.2500 0.034(3) Uani 1 2 d S . .
H9 H 0.4239 0.4239 0.2500 0.040 Uiso 1 2 calc SR . .
C10 C 0.7046(4) 0.7088(4) -0.1791 0.079(7) Uani 0.50 1 d PRDU . .
H10 H 0.6471 0.6776 -0.1417 0.094 Uiso 0.50 1 d PR . .
N1 N 0.7500 0.7500 -0.1056(12) 0.020(3) Uani 1 4 d S . .
Cu1 Cu 0.7500 0.7500 0.11775(16) 0.0195(7) Uani 1 4 d S . .
O1 O 0.6807(3) 0.6550(3) 0.1374(5) 0.0232(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.271(7) 7 ?
C1 O1 1.271(7) . ?
C1 C2 1.477(14) . ?
C2 C3 1.410(9) 7 ?
C2 C3 1.410(9) . ?
C3 C8 1.426(12) . ?
C3 C4 1.431(11) . ?
C4 C5 1.356(11) . ?
C5 C6 1.411(11) . ?
C6 C7 1.355(12) . ?
C7 C8 1.429(12) . ?
C8 C9 1.351(9) . ?
C9 C8 1.351(9) 7 ?
C10 N1 1.238(10) . ?
C10 C10 1.3627 7_554 ?
C10 C10 1.440(13) 4_565 ?
C10 C10 1.440(13) 3_655 ?
C10 C10 1.929(9) 6_564 ?
C10 C10 2.030(10) 5_654 ?
C10 C10 2.036(19) 2_665 ?
N1 C10 1.238(10) 2_665 ?
N1 C10 1.238(10) 3_655 ?
N1 C10 1.238(10) 4_565 ?
N1 Cu1 2.141(11) . ?
Cu1 O1 1.960(5) . ?
Cu1 O1 1.960(5) 3_655 ?
Cu1 O1 1.960(5) 2_665 ?
Cu1 O1 1.960(5) 4_565 ?
Cu1 Cu1 2.535(3) 5_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O1 123.6(10) 7 . ?
O1 C1 C2 118.2(5) 7 . ?
O1 C1 C2 118.2(5) . . ?
C3 C2 C3 121.0(10) 7 . ?
C3 C2 C1 119.5(5) 7 . ?
C3 C2 C1 119.5(5) . . ?
C2 C3 C8 119.3(8) . . ?
C2 C3 C4 122.9(8) . . ?
C8 C3 C4 117.8(7) . . ?
C5 C4 C3 121.0(8) . . ?
C4 C5 C6 121.1(8) . . ?
C7 C6 C5 119.9(8) . . ?
C6 C7 C8 121.1(8) . . ?
C9 C8 C3 115.4(7) . . ?
C9 C8 C7 125.5(8) . . ?
C3 C8 C7 119.0(8) . . ?
C8 C9 C8 129.6(10) 7 . ?
N1 C10 C10 124.4(5) . 7_554 ?
N1 C10 C10 54.4(3) . 4_565 ?
C10 C10 C10 92.8 7_554 4_565 ?
N1 C10 C10 54.4(3) . 3_655 ?
C10 C10 C10 86.9 7_554 3_655 ?
C10 C10 C10 90.0 4_565 3_655 ?
N1 C10 C10 90.5(6) . 6_564 ?
C10 C10 C10 48.2(3) 7_554 6_564 ?
C10 C10 C10 44.9(3) 4_565 6_564 ?
C10 C10 C10 92.0 3_655 6_564 ?
N1 C10 C10 85.9(6) . 5_654 ?
C10 C10 C10 45.1(3) 7_554 5_654 ?
C10 C10 C10 87.9 4_565 5_654 ?
C10 C10 C10 42.1(3) 3_655 5_654 ?
C10 C10 C10 61.8(3) 6_564 5_654 ?
N1 C10 C10 34.7(5) . 2_665 ?
C10 C10 C10 89.8 7_554 2_665 ?
C10 C10 C10 45.0 4_565 2_665 ?
C10 C10 C10 45.0 3_655 2_665 ?
C10 C10 C10 61.51(17) 6_564 2_665 ?
C10 C10 C10 56.65(13) 5_654 2_665 ?
C10 N1 C10 110.7(10) . 2_665 ?
C10 N1 C10 71.1(5) . 3_655 ?
C10 N1 C10 71.1(5) 2_665 3_655 ?
C10 N1 C10 71.1(5) . 4_565 ?
C10 N1 C10 71.1(5) 2_665 4_565 ?
C10 N1 C10 110.7(10) 3_655 4_565 ?
C10 N1 Cu1 124.7(5) . . ?
C10 N1 Cu1 124.7(5) 2_665 . ?
C10 N1 Cu1 124.7(5) 3_655 . ?
C10 N1 Cu1 124.7(5) 4_565 . ?
O1 Cu1 O1 89.47(3) . 3_655 ?
O1 Cu1 O1 169.0(3) . 2_665 ?
O1 Cu1 O1 89.47(3) 3_655 2_665 ?
O1 Cu1 O1 89.47(3) . 4_565 ?
O1 Cu1 O1 169.0(3) 3_655 4_565 ?
O1 Cu1 O1 89.47(3) 2_665 4_565 ?
O1 Cu1 N1 95.52(14) . . ?
O1 Cu1 N1 95.52(14) 3_655 . ?
O1 Cu1 N1 95.52(14) 2_665 . ?
O1 Cu1 N1 95.52(14) 4_565 . ?
O1 Cu1 Cu1 84.48(14) . 5_655 ?
O1 Cu1 Cu1 84.48(14) 3_655 5_655 ?
O1 Cu1 Cu1 84.48(14) 2_665 5_655 ?
O1 Cu1 Cu1 84.48(14) 4_565 5_655 ?
N1 Cu1 Cu1 180.000(1) . 5_655 ?
C1 O1 Cu1 120.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -61.1(4) 7 . . 7 ?
O1 C1 C2 C3 118.9(4) . . . 7 ?
O1 C1 C2 C3 118.9(4) 7 . . . ?
O1 C1 C2 C3 -61.1(4) . . . . ?
C3 C2 C3 C8 -0.4(5) 7 . . . ?
C1 C2 C3 C8 179.6(5) . . . . ?
C3 C2 C3 C4 178.0(8) 7 . . . ?
C1 C2 C3 C4 -2.0(8) . . . . ?
C2 C3 C4 C5 178.7(7) . . . . ?
C8 C3 C4 C5 -2.8(11) . . . . ?
C3 C4 C5 C6 0.1(12) . . . . ?
C4 C5 C6 C7 1.8(12) . . . . ?
C5 C6 C7 C8 -1.0(12) . . . . ?
C2 C3 C8 C9 0.9(10) . . . . ?
C4 C3 C8 C9 -177.7(6) . . . . ?
C2 C3 C8 C7 -177.9(6) . . . . ?
C4 C3 C8 C7 3.6(11) . . . . ?
C6 C7 C8 C9 179.6(7) . . . . ?
C6 C7 C8 C3 -1.8(12) . . . . ?
C3 C8 C9 C8 -0.4(5) . . . 7 ?
C7 C8 C9 C8 178.2(9) . . . 7 ?
C10 C10 N1 C10 5.0 7_554 . . 2_665 ?
C10 C10 N1 C10 -60.4(3) 4_565 . . 2_665 ?
C10 C10 N1 C10 60.4(3) 3_655 . . 2_665 ?
C10 C10 N1 C10 -31.69(15) 6_564 . . 2_665 ?
C10 C10 N1 C10 30.03(17) 5_654 . . 2_665 ?
C10 C10 N1 C10 -55.4(3) 7_554 . . 3_655 ?
C10 C10 N1 C10 -120.7(6) 4_565 . . 3_655 ?
C10 C10 N1 C10 -92.1(4) 6_564 . . 3_655 ?
C10 C10 N1 C10 -30.3(2) 5_654 . . 3_655 ?
C10 C10 N1 C10 -60.4(3) 2_665 . . 3_655 ?
C10 C10 N1 C10 65.4(3) 7_554 . . 4_565 ?
C10 C10 N1 C10 120.7(6) 3_655 . . 4_565 ?
C10 C10 N1 C10 28.7(3) 6_564 . . 4_565 ?
C10 C10 N1 C10 90.4(4) 5_654 . . 4_565 ?
C10 C10 N1 C10 60.4(3) 2_665 . . 4_565 ?
C10 C10 N1 Cu1 -175.00(3) 7_554 . . . ?
C10 C10 N1 Cu1 119.6(3) 4_565 . . . ?
C10 C10 N1 Cu1 -119.6(3) 3_655 . . . ?
C10 C10 N1 Cu1 148.31(15) 6_564 . . . ?
C10 C10 N1 Cu1 -149.97(17) 5_654 . . . ?
C10 C10 N1 Cu1 180.000(3) 2_665 . . . ?
C10 N1 Cu1 O1 11.66(15) . . . . ?
C10 N1 Cu1 O1 -168.34(15) 2_665 . . . ?
C10 N1 Cu1 O1 -78.34(15) 3_655 . . . ?
C10 N1 Cu1 O1 101.66(15) 4_565 . . . ?
C10 N1 Cu1 O1 101.66(15) . . . 3_655 ?
C10 N1 Cu1 O1 -78.34(15) 2_665 . . 3_655 ?
C10 N1 Cu1 O1 11.66(15) 3_655 . . 3_655 ?
C10 N1 Cu1 O1 -168.34(15) 4_565 . . 3_655 ?
C10 N1 Cu1 O1 -168.34(15) . . . 2_665 ?
C10 N1 Cu1 O1 11.66(15) 2_665 . . 2_665 ?
C10 N1 Cu1 O1 101.66(15) 3_655 . . 2_665 ?
C10 N1 Cu1 O1 -78.34(15) 4_565 . . 2_665 ?
C10 N1 Cu1 O1 -78.34(15) . . . 4_565 ?
C10 N1 Cu1 O1 101.66(15) 2_665 . . 4_565 ?
C10 N1 Cu1 O1 -168.34(15) 3_655 . . 4_565 ?
C10 N1 Cu1 O1 11.66(15) 4_565 . . 4_565 ?
C10 N1 Cu1 Cu1 127(100) . . . 5_655 ?
C10 N1 Cu1 Cu1 -53(100) 2_665 . . 5_655 ?
C10 N1 Cu1 Cu1 37(100) 3_655 . . 5_655 ?
C10 N1 Cu1 Cu1 -143(100) 4_565 . . 5_655 ?
O1 C1 O1 Cu1 -11.68(18) 7 . . . ?
C2 C1 O1 Cu1 168.32(18) . . . . ?
O1 Cu1 O1 C1 105.5(3) 3_655 . . . ?
O1 Cu1 O1 C1 21.0(3) 2_665 . . . ?
O1 Cu1 O1 C1 -63.5(4) 4_565 . . . ?
N1 Cu1 O1 C1 -159.0(3) . . . . ?
Cu1 Cu1 O1 C1 21.0(3) 5_655 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.046
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.093
_database_code_depnum_ccdc_archive 'CCDC 988619'
