# 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.
#
data_New

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Cu2 O10'
_chemical_formula_weight         665.54

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

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   R3m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   26.2119(14)
_cell_length_b                   26.2119(14)
_cell_length_c                   36.423(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     21672(2)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15427
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3023
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.879
_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            15427
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_sigmaI/netI    0.1840
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.35
_reflns_number_total             7352
_reflns_number_gt                3500
_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 -0.010 -0.016 0.008 17188 2429 ' '
_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^)+(0.0011P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.34(3)
_refine_ls_number_reflns         7352
_refine_ls_number_parameters     205
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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 0.19773(3) 0.39545(5) 0.03009(3) 0.0603(4) Uani 1 2 d S . .
Cu2 Cu 0.22983(3) 0.45967(5) -0.03008(3) 0.0601(4) Uani 1 2 d S . .
O1 O 0.3048(3) 0.5056(2) -0.00536(16) 0.0837(18) Uani 1 1 d . . .
O2 O 0.2738(2) 0.4481(2) 0.04740(17) 0.099(2) Uani 1 1 d . . .
O3 O 0.8188(2) 0.7385(2) 0.28687(14) 0.0837(17) Uani 1 1 d . . .
O4 O 0.7900(2) 0.6833(2) 0.33838(15) 0.0815(17) Uani 1 1 d . . .
O5 O 0.2567(2) 0.5133(5) -0.0815(2) 0.132(4) Uani 1 2 d S . .
O6 O 0.17423(17) 0.3485(3) 0.0810(2) 0.109(3) Uani 1 2 d S . .
C1 C 0.3096(4) 0.4897(4) 0.0297(2) 0.084(3) Uani 1 1 d U . .
C2 C 0.4098(2) 0.5902(2) 0.0252(3) 0.070(3) Uani 1 2 d S . .
H2A H 0.4017 0.5983 0.0017 0.084 Uiso 1 2 calc SR . .
C3 C 0.3714(3) 0.5372(3) 0.0463(2) 0.077(3) Uani 1 1 d . . .
C4 C 0.3847(3) 0.5233(3) 0.0812(2) 0.079(3) Uani 1 1 d . . .
H4A H 0.3579 0.4891 0.0934 0.095 Uiso 1 1 calc R . .
C5 C 0.4383(3) 0.5617(3) 0.0967(3) 0.111(6) Uani 1 2 d S . .
C6 C 0.4515(4) 0.5485(4) 0.1285(4) 0.119(6) Uani 1 2 d S . .
C7 C 0.4633(4) 0.5367(4) 0.1545(5) 0.125(5) Uani 1 2 d S . .
C8 C 0.4811(4) 0.5189(4) 0.1900(4) 0.122(5) Uani 1 2 d S . .
C9 C 0.5344(5) 0.5535(4) 0.2079(3) 0.127(4) Uani 1 1 d . . .
H9A H 0.5606 0.5888 0.1965 0.153 Uiso 1 1 calc R . .
C10 C 0.5530(4) 0.5410(4) 0.2412(3) 0.100(3) Uani 1 1 d . . .
C11 C 0.5130(3) 0.4870(3) 0.2588(3) 0.109(4) Uani 1 2 d S . .
H11A H 0.5220 0.4780 0.2817 0.130 Uiso 1 2 calc SR . .
C12 C 0.6135(5) 0.5833(5) 0.2600(3) 0.101(3) Uani 1 1 d . . .
C13 C 0.6579(6) 0.6269(5) 0.2401(3) 0.148(5) Uani 1 1 d . . .
H13A H 0.6510 0.6304 0.2154 0.177 Uiso 1 1 calc R . .
C14 C 0.7123(5) 0.6661(5) 0.2543(3) 0.129(4) Uani 1 1 d . . .
H14A H 0.7413 0.6972 0.2409 0.154 Uiso 1 1 calc R . .
C15 C 0.7195(4) 0.6553(4) 0.2891(2) 0.073(2) Uani 1 1 d . . .
C16 C 0.6791(5) 0.6131(5) 0.3094(3) 0.129(4) Uani 1 1 d . . .
H16A H 0.6887 0.6058 0.3327 0.155 Uiso 1 1 calc R . .
C17 C 0.6190(5) 0.5776(5) 0.2954(3) 0.141(4) Uani 1 1 d . . .
H17A H 0.5873 0.5530 0.3103 0.169 Uiso 1 1 calc R . .
C18 C 0.7809(3) 0.6931(3) 0.3060(2) 0.058(2) Uani 1 1 d . . .

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 0.0632(6) 0.0437(8) 0.0676(8) -0.0005(7) -0.0003(3) 0.0218(4)
Cu2 0.0630(7) 0.0458(8) 0.0657(7) 0.0008(7) 0.0004(3) 0.0229(4)
O1 0.088(4) 0.081(4) 0.088(4) -0.007(3) -0.005(3) 0.046(4)
O2 0.075(4) 0.045(4) 0.150(6) 0.049(4) 0.023(4) 0.010(3)
O3 0.084(4) 0.067(4) 0.076(4) 0.002(3) -0.018(3) 0.020(3)
O4 0.075(4) 0.072(4) 0.085(4) -0.003(3) -0.015(3) 0.027(3)
O5 0.139(6) 0.193(10) 0.081(5) 0.039(6) 0.019(3) 0.097(5)
O6 0.135(6) 0.073(6) 0.097(5) 0.024(5) 0.012(2) 0.037(3)
C1 0.094(6) 0.107(6) 0.084(5) -0.058(5) -0.062(5) 0.074(5)
C2 0.048(5) 0.048(5) 0.092(7) 0.006(3) -0.006(3) 0.007(6)
C3 0.023(4) 0.056(5) 0.140(7) 0.010(5) -0.010(5) 0.010(4)
C4 0.043(5) 0.061(5) 0.097(6) 0.029(5) -0.037(5) 0.000(4)
C5 0.084(6) 0.084(6) 0.075(8) 0.053(5) -0.053(5) -0.025(7)
C6 0.121(9) 0.121(9) 0.091(10) 0.023(5) -0.023(5) 0.043(10)
C7 0.120(9) 0.120(9) 0.128(13) 0.006(6) -0.006(6) 0.055(11)
C8 0.089(7) 0.089(7) 0.133(13) -0.003(6) 0.003(6) 0.002(9)
C9 0.130(9) 0.093(8) 0.122(8) 0.028(7) 0.008(8) 0.028(7)
C10 0.104(8) 0.086(7) 0.095(6) 0.023(6) 0.007(6) 0.037(6)
C11 0.109(8) 0.109(8) 0.105(10) 0.005(4) -0.005(4) 0.053(10)
C12 0.082(8) 0.095(8) 0.109(8) 0.004(7) -0.015(7) 0.032(7)
C13 0.112(10) 0.133(11) 0.140(10) 0.017(9) 0.006(9) 0.017(9)
C14 0.109(10) 0.126(10) 0.117(9) -0.010(7) -0.035(8) 0.033(8)
C15 0.068(6) 0.073(6) 0.067(5) -0.004(5) -0.021(5) 0.027(5)
C16 0.100(8) 0.113(9) 0.129(8) 0.041(8) -0.013(8) 0.019(7)
C17 0.123(10) 0.135(10) 0.121(9) 0.032(8) -0.026(8) 0.031(8)
C18 0.066(6) 0.052(5) 0.059(5) 0.006(4) 0.010(5) 0.031(4)

_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 1.878(6) . ?
Cu1 O2 1.878(6) 6 ?
Cu1 O4 1.932(5) 13_444 ?
Cu1 O4 1.933(5) 18_544 ?
Cu1 O6 2.141(7) . ?
Cu1 Cu2 2.6320(15) . ?
Cu2 O3 1.907(5) 13_444 ?
Cu2 O3 1.908(5) 18_544 ?
Cu2 O1 1.939(6) . ?
Cu2 O1 1.939(6) 6 ?
Cu2 O5 2.233(8) . ?
O1 C1 1.369(9) . ?
O2 C1 1.208(11) . ?
O3 C18 1.305(8) . ?
O3 Cu2 1.907(5) 7 ?
O4 C18 1.256(8) . ?
O4 Cu1 1.932(5) 7 ?
C1 C3 1.588(10) . ?
C2 C3 1.462(9) . ?
C2 C3 1.462(9) 4_665 ?
C2 H2A 0.9300 . ?
C3 C4 1.415(9) . ?
C4 C5 1.376(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.304(15) . ?
C5 C4 1.376(8) 4_665 ?
C6 C7 1.086(16) . ?
C7 C8 1.527(19) . ?
C8 C9 1.388(11) 4_665 ?
C8 C9 1.388(11) . ?
C9 C10 1.405(11) . ?
C9 H9A 0.9300 . ?
C10 C11 1.425(9) . ?
C10 C12 1.567(12) . ?
C11 C10 1.425(9) 4_665 ?
C11 H11A 0.9300 . ?
C12 C17 1.315(11) . ?
C12 C13 1.362(12) . ?
C13 C14 1.374(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.331(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.313(10) . ?
C15 C18 1.534(10) . ?
C16 C17 1.464(12) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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 88.1(4) . 6 ?
O2 Cu1 O4 170.2(3) . 13_444 ?
O2 Cu1 O4 90.6(2) 6 13_444 ?
O2 Cu1 O4 90.6(2) . 18_544 ?
O2 Cu1 O4 170.2(3) 6 18_544 ?
O4 Cu1 O4 89.1(3) 13_444 18_544 ?
O2 Cu1 O6 91.5(2) . . ?
O2 Cu1 O6 91.5(2) 6 . ?
O4 Cu1 O6 98.2(2) 13_444 . ?
O4 Cu1 O6 98.2(2) 18_544 . ?
O2 Cu1 Cu2 85.83(18) . . ?
O2 Cu1 Cu2 85.83(18) 6 . ?
O4 Cu1 Cu2 84.43(18) 13_444 . ?
O4 Cu1 Cu2 84.43(18) 18_544 . ?
O6 Cu1 Cu2 176.3(2) . . ?
O3 Cu2 O3 87.8(3) 13_444 18_544 ?
O3 Cu2 O1 169.2(3) 13_444 . ?
O3 Cu2 O1 90.4(2) 18_544 . ?
O3 Cu2 O1 90.4(2) 13_444 6 ?
O3 Cu2 O1 169.2(3) 18_544 6 ?
O1 Cu2 O1 89.4(3) . 6 ?
O3 Cu2 O5 95.3(2) 13_444 . ?
O3 Cu2 O5 95.3(2) 18_544 . ?
O1 Cu2 O5 95.5(3) . . ?
O1 Cu2 O5 95.5(3) 6 . ?
O3 Cu2 Cu1 84.33(16) 13_444 . ?
O3 Cu2 Cu1 84.33(16) 18_544 . ?
O1 Cu2 Cu1 84.91(18) . . ?
O1 Cu2 Cu1 84.91(18) 6 . ?
O5 Cu2 Cu1 179.4(3) . . ?
C1 O1 Cu2 117.5(5) . . ?
C1 O2 Cu1 122.9(6) . . ?
C18 O3 Cu2 123.8(5) . 7 ?
C18 O4 Cu1 123.6(5) . 7 ?
O2 C1 O1 128.7(8) . . ?
O2 C1 C3 122.2(8) . . ?
O1 C1 C3 109.1(9) . . ?
C3 C2 C3 110.1(10) . 4_665 ?
C3 C2 H2A 125.0 . . ?
C3 C2 H2A 125.0 4_665 . ?
C4 C3 C2 125.2(7) . . ?
C4 C3 C1 115.2(7) . . ?
C2 C3 C1 119.6(8) . . ?
C5 C4 C3 118.3(7) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C6 C5 C4 118.7(5) . 4_665 ?
C6 C5 C4 118.7(5) . . ?
C4 C5 C4 122.5(9) 4_665 . ?
C7 C6 C5 178(2) . . ?
C6 C7 C8 178(2) . . ?
C9 C8 C9 112.1(15) 4_665 . ?
C9 C8 C7 124.0(7) 4_665 . ?
C9 C8 C7 124.0(7) . . ?
C8 C9 C10 127.2(10) . . ?
C8 C9 H9A 116.4 . . ?
C10 C9 H9A 116.4 . . ?
C9 C10 C11 116.8(10) . . ?
C9 C10 C12 124.1(8) . . ?
C11 C10 C12 119.2(9) . . ?
C10 C11 C10 119.7(12) . 4_665 ?
C10 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 4_665 . ?
C17 C12 C13 121.4(11) . . ?
C17 C12 C10 118.6(10) . . ?
C13 C12 C10 119.9(10) . . ?
C12 C13 C14 123.9(11) . . ?
C12 C13 H13A 118.0 . . ?
C14 C13 H13A 118.0 . . ?
C15 C14 C13 113.9(11) . . ?
C15 C14 H14A 123.1 . . ?
C13 C14 H14A 123.1 . . ?
C16 C15 C14 125.1(9) . . ?
C16 C15 C18 117.5(8) . . ?
C14 C15 C18 117.4(9) . . ?
C15 C16 C17 119.8(9) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C12 C17 C16 114.5(10) . . ?
C12 C17 H17A 122.8 . . ?
C16 C17 H17A 122.8 . . ?
O4 C18 O3 123.5(7) . . ?
O4 C18 C15 119.3(7) . . ?
O3 C18 C15 116.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 969712'