# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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. 
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data_New
_database_code_depnum_ccdc_archive 'CCDC 928170'
#TrackingRef 'ZJU-5.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C63 H39 Cu6 N3 O30'
_chemical_formula_weight         1699.21
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           Hexagonal
_symmetry_space_group_name_H-M   R-3m
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
_cell_length_a                   18.8163(13)
_cell_length_b                   18.8163(13)
_cell_length_c                   38.079(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11675.7(16)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8052
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      25.06
_exptl_crystal_description       green
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2556
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   CrysAlisPro
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8052
_diffrn_reflns_av_R_equivalents  0.1711
_diffrn_reflns_av_sigmaI/netI    0.1475
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2502
_reflns_number_gt                1566
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.049 -0.033 -0.002 8241 1447 ' '
_platon_squeeze_details          
;
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0813P)^2^+12.3550P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2502
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0935
_refine_ls_wR_factor_ref         0.2233
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.04598(5) 0.52299(3) 0.02875(2) 0.0336(4) Uani 1 2 d S . .
O1 O 0.1115(2) 0.4830(3) 0.00459(10) 0.0508(11) Uani 1 1 d . . .
O2 O 0.0319(2) 0.4446(3) -0.04409(10) 0.0495(11) Uani 1 1 d . . .
O3 O 0.1083(6) 0.5541(3) 0.07814(19) 0.105(3) Uani 1 2 d S . .
C1 C 0.0945(3) 0.4555(4) -0.02616(17) 0.0505(16) Uani 1 1 d . . .
C2 C 0.1531(4) 0.4337(4) -0.04347(14) 0.0479(15) Uani 1 1 d . . .
C3 C 0.2244(3) 0.4488(5) -0.0265(2) 0.046(2) Uani 1 2 d S . .
H3A H 0.2346 0.4692 -0.0037 0.055 Uiso 1 2 calc SR . .
C4 C 0.1386(4) 0.4047(4) -0.07814(15) 0.0544(16) Uani 1 1 d . . .
H4A H 0.0913 0.3960 -0.0897 0.065 Uiso 1 1 calc R . .
C5 C 0.1944(3) 0.3889(7) -0.0954(2) 0.065(3) Uani 1 2 d S . .
C6 C 0.1810(4) 0.3620(7) -0.1327(3) 0.068(3) Uani 1 2 d S . .
C7 C 0.1028(11) 0.3119(14) -0.1443(3) 0.086(5) Uani 0.38 1 d P . .
N1 N 0.1028(11) 0.3119(14) -0.1443(3) 0.086(5) Uani 0.13 1 d P . .
C7' C 0.1391(12) 0.3851(16) -0.1542(5) 0.101(7) Uani 0.38 1 d P . 1
N1' N 0.1391(12) 0.3851(16) -0.1542(5) 0.101(7) Uani 0.13 1 d P . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0276(5) 0.0422(5) 0.0261(6) -0.00071(18) -0.0014(4) 0.0138(3)
O1 0.046(2) 0.079(3) 0.038(2) -0.012(2) -0.0054(19) 0.040(2)
O2 0.040(2) 0.071(3) 0.037(2) -0.016(2) -0.0006(19) 0.028(2)
O3 0.126(7) 0.125(5) 0.065(5) -0.032(2) -0.064(5) 0.063(4)
C1 0.029(3) 0.060(4) 0.054(4) 0.001(3) 0.003(3) 0.015(3)
C2 0.046(3) 0.066(4) 0.036(3) -0.002(3) 0.003(3) 0.032(3)
C3 0.042(3) 0.063(5) 0.039(4) -0.006(4) -0.003(2) 0.032(3)
C4 0.041(3) 0.085(5) 0.044(3) -0.015(3) -0.013(3) 0.036(4)
C5 0.050(4) 0.113(9) 0.053(6) -0.035(6) -0.017(3) 0.056(4)
C6 0.055(4) 0.115(9) 0.055(6) -0.043(6) -0.022(3) 0.057(4)
C7 0.101(13) 0.151(17) 0.027(7) -0.032(9) -0.006(8) 0.078(13)
N1 0.101(13) 0.151(17) 0.027(7) -0.032(9) -0.006(8) 0.078(13)
C7' 0.092(13) 0.19(2) 0.081(13) -0.028(14) -0.021(10) 0.115(16)
N1' 0.092(13) 0.19(2) 0.081(13) -0.028(14) -0.021(10) 0.115(16)
_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 O2 1.936(4) 19_565 ?
Cu1 O2 1.937(4) 6 ?
Cu1 O1 1.965(4) . ?
Cu1 O1 1.965(4) 24_565 ?
Cu1 O3 2.137(6) . ?
Cu1 Cu1 2.6531(17) 19_565 ?
O1 C1 1.255(7) . ?
O2 C1 1.287(7) . ?
O2 Cu1 1.937(4) 19_565 ?
C1 C2 1.508(8) . ?
C2 C3 1.384(7) . ?
C2 C4 1.402(8) . ?
C3 C2 1.384(7) 23 ?
C4 C5 1.393(7) . ?
C5 C4 1.393(7) 23 ?
C5 C6 1.485(13) . ?
C6 N1' 1.351(18) 23 ?
C6 C7' 1.351(18) 23 ?
C6 C7' 1.351(18) . ?
C6 N1 1.364(19) 23 ?
C6 C7 1.364(19) 23 ?
C6 C7 1.364(19) . ?
C7 C7' 1.25(3) . ?
C7 N1' 1.414(17) 17_554 ?
C7 C7' 1.414(17) 17_554 ?
C7 C7 1.84(3) 17_554 ?
C7 N1 1.84(3) 17_554 ?
C7 C7 2.00(4) 23 ?
C7' N1 1.414(17) 17_554 ?
C7' C7 1.414(17) 17_554 ?
C7' N1' 1.93(4) 17_554 ?
C7' C7' 1.93(4) 17_554 ?
C7' C7' 2.01(3) 23 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 87.7(3) 19_565 6 ?
O2 Cu1 O1 168.49(16) 19_565 . ?
O2 Cu1 O1 90.82(19) 6 . ?
O2 Cu1 O1 90.82(19) 19_565 24_565 ?
O2 Cu1 O1 168.49(16) 6 24_565 ?
O1 Cu1 O1 88.3(3) . 24_565 ?
O2 Cu1 O3 92.6(2) 19_565 . ?
O2 Cu1 O3 92.6(2) 6 . ?
O1 Cu1 O3 98.9(2) . . ?
O1 Cu1 O3 98.9(2) 24_565 . ?
O2 Cu1 Cu1 83.05(12) 19_565 19_565 ?
O2 Cu1 Cu1 83.05(12) 6 19_565 ?
O1 Cu1 Cu1 85.44(11) . 19_565 ?
O1 Cu1 Cu1 85.44(11) 24_565 19_565 ?
O3 Cu1 Cu1 174.0(3) . 19_565 ?
C1 O1 Cu1 121.0(4) . . ?
C1 O2 Cu1 124.5(4) . 19_565 ?
O1 C1 O2 125.9(5) . . ?
O1 C1 C2 116.7(5) . . ?
O2 C1 C2 117.4(5) . . ?
C3 C2 C4 119.9(6) . . ?
C3 C2 C1 120.4(5) . . ?
C4 C2 C1 119.4(5) . . ?
C2 C3 C2 120.2(7) 23 . ?
C5 C4 C2 120.5(6) . . ?
C4 C5 C4 119.0(8) 23 . ?
C4 C5 C6 120.4(4) 23 . ?
C4 C5 C6 120.4(4) . . ?
N1' C6 C7' 0.0(17) 23 23 ?
N1' C6 C7' 96.2(19) 23 . ?
C7' C6 C7' 96.2(19) 23 . ?
N1' C6 N1 54.8(11) 23 23 ?
C7' C6 N1 54.8(11) 23 23 ?
C7' C6 N1 121.0(11) . 23 ?
N1' C6 C7 54.8(11) 23 23 ?
C7' C6 C7 54.8(11) 23 23 ?
C7' C6 C7 121.0(11) . 23 ?
N1 C6 C7 0.0(15) 23 23 ?
N1' C6 C7 121.0(11) 23 . ?
C7' C6 C7 121.0(11) 23 . ?
C7' C6 C7 54.8(11) . . ?
N1 C6 C7 94.2(17) 23 . ?
C7 C6 C7 94.2(17) 23 . ?
N1' C6 C5 119.9(10) 23 . ?
C7' C6 C5 119.9(10) 23 . ?
C7' C6 C5 119.9(9) . . ?
N1 C6 C5 119.1(8) 23 . ?
C7 C6 C5 119.1(8) 23 . ?
C7 C6 C5 119.1(8) . . ?
C7' C7 C6 62.0(13) . . ?
C7' C7 N1' 93(2) . 17_554 ?
C6 C7 N1' 121.1(15) . 17_554 ?
C7' C7 C7' 93(2) . 17_554 ?
C6 C7 C7' 121.1(15) . 17_554 ?
N1' C7 C7' 0.0(5) 17_554 17_554 ?
C7' C7 C7 50.1(13) . 17_554 ?
C6 C7 C7 94.2(15) . 17_554 ?
N1' C7 C7 42.7(11) 17_554 17_554 ?
C7' C7 C7 42.7(11) 17_554 17_554 ?
C7' C7 N1 50.1(13) . 17_554 ?
C6 C7 N1 94.2(15) . 17_554 ?
N1' C7 N1 42.7(11) 17_554 17_554 ?
C7' C7 N1 42.7(11) 17_554 17_554 ?
C7 C7 N1 0.0(13) 17_554 17_554 ?
C7' C7 C7 90.3(12) . 23 ?
C6 C7 C7 42.9(9) . 23 ?
N1' C7 C7 90.2(10) 17_554 23 ?
C7' C7 C7 90.2(10) 17_554 23 ?
C7 C7 C7 89.996(2) 17_554 23 ?
N1 C7 C7 89.996(2) 17_554 23 ?
C7 C7' C6 63.1(14) . . ?
C7 C7' N1 87(2) . 17_554 ?
C6 C7' N1 118.0(17) . 17_554 ?
C7 C7' C7 87(2) . 17_554 ?
C6 C7' C7 118.0(17) . 17_554 ?
N1 C7' C7 0.0(18) 17_554 17_554 ?
C7 C7' N1' 46.9(13) . 17_554 ?
C6 C7' N1' 93.2(17) . 17_554 ?
N1 C7' N1' 40.2(10) 17_554 17_554 ?
C7 C7' N1' 40.2(10) 17_554 17_554 ?
C7 C7' C7' 46.9(13) . 17_554 ?
C6 C7' C7' 93.2(17) . 17_554 ?
N1 C7' C7' 40.2(10) 17_554 17_554 ?
C7 C7' C7' 40.2(10) 17_554 17_554 ?
N1' C7' C7' 0.0(13) 17_554 17_554 ?
C7 C7' C7' 89.7(12) . 23 ?
C6 C7' C7' 41.9(9) . 23 ?
N1 C7' C7' 89.8(10) 17_554 23 ?
C7 C7' C7' 89.8(10) 17_554 23 ?
N1' C7' C7' 89.997(2) 17_554 23 ?
C7' C7' C7' 89.997(2) 17_554 23 ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.110