# Electronic Supplementary Material (ESI) for CrystEngComm
# 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_bb

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H14 Cu3 O15 '
_chemical_formula_sum            'C34 H14 Cu3 O15 '
_chemical_formula_weight         853.10

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           Hexagonal
_symmetry_space_group_name_H-M   'P 63/m m c'
_symmetry_space_group_name_Hall  '-P 6c 2c'



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

_cell_length_a                   18.961(4)
_cell_length_b                   18.961(4)
_cell_length_c                   50.901(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     15848(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4718
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      18.90

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2550.0
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            78863
_diffrn_reflns_av_R_equivalents  0.1858
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5209
_reflns_number_gt                2516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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. 
;

_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^)+(0.2000P)^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_number_reflns         5205
_refine_ls_number_parameters     135
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.1023
_refine_ls_wR_factor_ref         0.3758
_refine_ls_wR_factor_gt          0.3400
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.002

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 -0.058 -0.037 -0.002 9951 9202 ' '


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 0.06030(11) 0.1206(2) 0.2500 0.1065(12) Uani 1 4 d S . .
Cu2 Cu 0.52214(3) 0.04429(7) -0.02190(2) 0.0371(4) Uani 1 2 d S . .
O1 O 0.1323(6) 0.1200(6) 0.2230(2) 0.155(4) Uani 1 1 d U . .
O2 O 0.4835(3) 0.1113(3) -0.00469(10) 0.0547(15) Uani 1 1 d . . .
O3 O 0.4447(3) 0.0353(3) 0.03185(10) 0.0537(14) Uani 1 1 d . . .
O4 O 0.5515(3) 0.1031(5) -0.05957(16) 0.084(3) Uani 1 2 d S . .
O5 O 0.1363(10) 0.273(2) 0.2500 0.287(2) Uani 1 4 d SU . .
C1 C 0.1302(16) 0.0651(8) 0.2147(3) 0.148(10) Uani 1 2 d S . .
C2 C 0.1926(11) 0.0963(5) 0.1879(3) 0.102(6) Uani 1 2 d S . .
C3 C 0.2113(10) 0.0451(8) 0.1757(2) 0.156(7) Uani 1 1 d . . .
H3 H 0.1977 -0.0041 0.1838 0.187 Uiso 1 1 calc R . .
C4 C 0.2496(11) 0.0622(8) 0.1518(3) 0.172(8) Uani 1 1 d . . .
H4 H 0.2612 0.0252 0.1437 0.206 Uiso 1 1 calc R . .
C5 C 0.2703(13) 0.1352(6) 0.1401(3) 0.126(7) Uani 1 2 d S . .
C6 C 0.3109(12) 0.1554(6) 0.1140(3) 0.112(7) Uani 1 2 d S . .
C7 C 0.3415(11) 0.1707(6) 0.0937(3) 0.097(5) Uani 1 2 d S . .
C8 C 0.3768(9) 0.1884(4) 0.0678(2) 0.077(4) Uani 1 2 d S . .
C9 C 0.3962(6) 0.1342(5) 0.05557(16) 0.068(3) Uani 1 1 d . . .
H9 H 0.3857 0.0865 0.0641 0.081 Uiso 1 1 calc R . .
C10 C 0.4316(5) 0.1520(5) 0.03032(14) 0.049(2) Uani 1 1 d . . .
C11 C 0.4486(7) 0.2243(3) 0.0183(2) 0.046(3) Uani 1 2 d S . .
H11 H 0.4720 0.2360 0.0016 0.056 Uiso 1 2 calc SR . .
C12 C 0.4547(5) 0.0946(4) 0.01860(14) 0.0463(19) 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 0.1241(17) 0.194(3) 0.0249(11) 0.000 0.000 0.0969(17)
Cu2 0.0451(7) 0.0311(7) 0.0305(7) 0.0061(5) 0.0031(3) 0.0156(4)
O1 0.155(4) 0.155(4) 0.154(4) 0.0000(10) 0.0015(10) 0.078(2)
O2 0.081(4) 0.050(3) 0.042(3) 0.010(2) 0.012(3) 0.040(3)
O3 0.079(4) 0.045(3) 0.044(3) 0.013(2) 0.017(3) 0.037(3)
O4 0.114(6) 0.067(6) 0.055(5) 0.026(5) 0.013(2) 0.034(3)
O5 0.287(3) 0.287(2) 0.287(3) 0.000 0.000 0.1437(11)
C1 0.30(3) 0.152(12) 0.040(8) -0.026(6) -0.052(13) 0.150(16)
C2 0.114(14) 0.136(12) 0.049(9) 0.010(4) 0.019(9) 0.057(7)
C3 0.253(18) 0.136(13) 0.082(9) 0.051(8) 0.095(11) 0.101(13)
C4 0.31(2) 0.138(12) 0.110(10) 0.070(9) 0.126(13) 0.144(14)
C5 0.21(2) 0.128(10) 0.068(10) 0.037(6) 0.074(12) 0.104(10)
C6 0.188(19) 0.102(8) 0.077(10) 0.035(6) 0.070(12) 0.094(9)
C7 0.163(16) 0.089(7) 0.065(9) 0.031(5) 0.062(10) 0.081(8)
C8 0.120(12) 0.069(6) 0.059(8) 0.022(4) 0.044(8) 0.060(6)
C9 0.092(7) 0.054(5) 0.065(5) 0.027(4) 0.030(5) 0.042(5)
C10 0.056(5) 0.046(5) 0.046(4) 0.002(4) 0.010(4) 0.027(4)
C11 0.057(7) 0.043(4) 0.044(6) 0.008(3) 0.015(5) 0.029(3)
C12 0.053(5) 0.034(4) 0.047(5) -0.003(4) 0.004(4) 0.018(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 O1 1.942(11) 20 ?
Cu1 O1 1.942(11) 11 ?
Cu1 O1 1.942(11) . ?
Cu1 O1 1.942(11) 16_556 ?
Cu2 O2 1.963(5) 20_655 ?
Cu2 O2 1.963(5) . ?
Cu2 O3 1.969(5) 13_655 ?
Cu2 O3 1.969(5) 8 ?
Cu2 O4 2.147(8) . ?
Cu2 Cu2 2.662(2) 13_655 ?
O1 C1 1.105(11) . ?
O2 C12 1.277(8) . ?
O3 C12 1.241(8) . ?
O3 Cu2 1.969(5) 13_655 ?
C1 O1 1.105(11) 24 ?
C1 C2 1.71(3) . ?
C2 C3 1.342(14) 24 ?
C2 C3 1.342(14) . ?
C3 C4 1.370(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(13) . ?
C4 H4 0.9300 . ?
C5 C4 1.370(13) 24 ?
C5 C6 1.486(18) . ?
C6 C7 1.149(16) . ?
C7 C8 1.439(16) . ?
C8 C9 1.398(10) . ?
C8 C9 1.398(10) 24 ?
C9 C10 1.411(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(9) . ?
C10 C12 1.486(10) . ?
C11 C10 1.385(9) 24 ?
C11 H11 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
O1 Cu1 O1 90.2(6) 20 11 ?
O1 Cu1 O1 89.8(6) 20 . ?
O1 Cu1 O1 179.5(7) 11 . ?
O1 Cu1 O1 179.5(7) 20 16_556 ?
O1 Cu1 O1 89.8(6) 11 16_556 ?
O1 Cu1 O1 90.2(6) . 16_556 ?
O2 Cu2 O2 88.4(3) 20_655 . ?
O2 Cu2 O3 89.9(2) 20_655 13_655 ?
O2 Cu2 O3 167.6(2) . 13_655 ?
O2 Cu2 O3 167.6(2) 20_655 8 ?
O2 Cu2 O3 89.9(2) . 8 ?
O3 Cu2 O3 89.2(3) 13_655 8 ?
O2 Cu2 O4 98.4(2) 20_655 . ?
O2 Cu2 O4 98.4(2) . . ?
O3 Cu2 O4 93.9(2) 13_655 . ?
O3 Cu2 O4 94.0(2) 8 . ?
O2 Cu2 Cu2 86.13(14) 20_655 13_655 ?
O2 Cu2 Cu2 86.13(14) . 13_655 ?
O3 Cu2 Cu2 81.52(14) 13_655 13_655 ?
O3 Cu2 Cu2 81.52(14) 8 13_655 ?
O4 Cu2 Cu2 173.6(3) . 13_655 ?
C1 O1 Cu1 125.4(17) . . ?
C12 O2 Cu2 120.3(5) . . ?
C12 O3 Cu2 126.3(5) . 13_655 ?
O1 C1 O1 135.3(19) . 24 ?
O1 C1 C2 106.5(15) . . ?
O1 C1 C2 106.5(15) 24 . ?
C3 C2 C3 117.7(15) 24 . ?
C3 C2 C1 120.6(8) 24 . ?
C3 C2 C1 120.6(8) . . ?
C2 C3 C4 122.7(14) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 118.4(13) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C4 120.0(15) . 24 ?
C4 C5 C6 120.0(8) . . ?
C4 C5 C6 120.0(8) 24 . ?
C7 C6 C5 179(2) . . ?
C6 C7 C8 178(2) . . ?
C9 C8 C9 120.0(11) . 24 ?
C9 C8 C7 119.9(5) . . ?
C9 C8 C7 119.9(5) 24 . ?
C8 C9 C10 119.9(8) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.1(7) . . ?
C11 C10 C12 122.6(7) . . ?
C9 C10 C12 118.1(7) . . ?
C10 C11 C10 121.8(9) . 24 ?
C10 C11 H11 119.1 . . ?
C10 C11 H11 119.1 24 . ?
O3 C12 O2 125.6(7) . . ?
O3 C12 C10 118.5(7) . . ?
O2 C12 C10 115.9(7) . . ?

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 Cu1 O1 C1 -92.6(16) 20 . . . ?
O1 Cu1 O1 C1 -3(11) 11 . . . ?
O1 Cu1 O1 C1 86.9(16) 16_556 . . . ?
O2 Cu2 O2 C12 -85.4(6) 20_655 . . . ?
O3 Cu2 O2 C12 -3.2(14) 13_655 . . . ?
O3 Cu2 O2 C12 82.3(6) 8 . . . ?
O4 Cu2 O2 C12 176.3(6) . . . . ?
Cu2 Cu2 O2 C12 0.8(6) 13_655 . . . ?
Cu1 O1 C1 O1 -55(5) . . . 24 ?
Cu1 O1 C1 C2 169.1(9) . . . . ?
O1 C1 C2 C3 -22(3) . . . 24 ?
O1 C1 C2 C3 -171.1(18) 24 . . 24 ?
O1 C1 C2 C3 171.1(18) . . . . ?
O1 C1 C2 C3 22(3) 24 . . . ?
C3 C2 C3 C4 1(4) 24 . . . ?
C1 C2 C3 C4 168.9(16) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C4 -3(4) . . . 24 ?
C3 C4 C5 C6 -179.2(18) . . . . ?
C4 C5 C6 C7 88(74) . . . . ?
C4 C5 C6 C7 -88(72) 24 . . . ?
C5 C6 C7 C8 0(71) . . . . ?
C6 C7 C8 C9 -92(6) . . . . ?
C6 C7 C8 C9 92(5) . . . 24 ?
C9 C8 C9 C10 -3(2) 24 . . . ?
C7 C8 C9 C10 -179.3(13) . . . . ?
C8 C9 C10 C11 1.6(15) . . . . ?
C8 C9 C10 C12 177.2(10) . . . . ?
C9 C10 C11 C10 -0.1(17) . . . 24 ?
C12 C10 C11 C10 -175.5(6) . . . 24 ?
Cu2 O3 C12 O2 5.0(12) 13_655 . . . ?
Cu2 O3 C12 C10 -175.2(5) 13_655 . . . ?
Cu2 O2 C12 O3 -3.5(11) . . . . ?
Cu2 O2 C12 C10 176.6(5) . . . . ?
C11 C10 C12 O3 172.8(8) . . . . ?
C9 C10 C12 O3 -2.6(12) . . . . ?
C11 C10 C12 O2 -7.4(12) . . . . ?
C9 C10 C12 O2 177.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.976
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.184
_database_code_depnum_ccdc_archive 'CCDC 943625'