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

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_ZJU-24

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8 Cu2 O14'
_chemical_formula_weight         647.38

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'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   18.6935(7)
_cell_length_b                   18.6935(7)
_cell_length_c                   38.3901(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11618.0(9)
_cell_formula_units_Z            9
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9150
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      23.37

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.833
_exptl_crystal_F_000             2898
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.860
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41989
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.365
_diffrn_reflns_theta_max         26.023
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2800
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1288P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2800
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.85664(2) 0.14336(2) 0.13827(2) 0.0380(3) Uani 1 2 d S T P . .
O1 O 0.7753(2) 0.07698(17) 0.21054(7) 0.0578(7) Uani 1 1 d . . . . .
O2 O 0.81534(18) 0.03842(17) 0.16301(7) 0.0565(8) Uani 1 1 d . . . . .
O3 O 0.89023(18) 0.10977(18) 0.08982(14) 0.109(2) Uani 1 2 d S T P . .
O4 O 0.5366(9) -0.3044(11) 0.2627(5) 0.234(8) Uani 0.5 1 d . . P . .
O5 O 0.5512(15) -0.3721(8) 0.2952(4) 0.314(14) Uani 0.5 1 d . . P . .
C1 C 0.7860(2) 0.0271(2) 0.19320(10) 0.0459(9) Uani 1 1 d . . . . .
C2 C 0.7798(4) -0.11009(19) 0.19354(14) 0.0519(14) Uani 1 2 d S T P . .
H2 H 0.8014 -0.0993 0.1711 0.062 Uiso 1 2 calc R U P . .
C3 C 0.7639(2) -0.0535(2) 0.21011(10) 0.0504(10) Uani 1 1 d . . . . .
C4 C 0.7327(3) -0.0689(3) 0.24414(11) 0.0583(11) Uani 1 1 d . . . . .
H4 H 0.7231 -0.0305 0.2554 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7156(4) -0.1422(2) 0.26148(16) 0.0616(17) Uani 1 2 d S T P . .
C6 C 0.6862(5) -0.1569(2) 0.29758(16) 0.0611(16) Uani 1 2 d S T P . .
C7 C 0.6239(7) -0.2318(6) 0.3091(2) 0.077(3) Uani 0.5 1 d . . P . .
C8 C 0.7242(7) -0.0917(6) 0.3216(2) 0.079(3) Uani 0.5 1 d . . P . .
H8 H 0.7612 -0.0393 0.3132 0.095 Uiso 0.5 1 calc . U P . .
C9 C 0.5736(12) -0.3081(11) 0.2858(5) 0.133(6) Uani 0.5 1 d . . P . .


_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 1.957(3) . ?
Cu1 O2 1.957(3) 22_665 ?
Cu1 O1 1.966(3) 10_545 ?
Cu1 O1 1.966(3) 25_655 ?
Cu1 O3 2.155(4) . ?
Cu1 Cu1 2.6518(11) 25_655 ?
O1 C1 1.241(4) . ?
O1 Cu1 1.966(3) 25_655 ?
O2 C1 1.254(4) . ?
O4 C9 1.148(19) . ?
O5 C9 1.11(2) . ?
C1 C3 1.496(5) . ?
C2 C3 1.389(5) . ?
C2 C3 1.389(5) 24_545 ?
C3 C4 1.401(5) . ?
C4 C5 1.408(5) . ?
C5 C4 1.408(5) 24_545 ?
C5 C6 1.466(8) . ?
C6 C7 1.371(11) 24_545 ?
C6 C7 1.372(11) . ?
C6 C8 1.406(11) . ?
C6 C8 1.406(11) 24_545 ?
C7 C8 1.402(12) 31_645 ?
C7 C9 1.541(19) . ?
C7 C7 1.64(2) 24_545 ?
C7 C8 1.694(15) 24_545 ?
C8 C7 1.402(12) 31_645 ?
C8 C7 1.694(15) 24_545 ?
C8 C8 1.73(2) 24_545 ?

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 88.58(17) . 22_665 ?
O2 Cu1 O1 89.72(13) . 10_545 ?
O2 Cu1 O1 167.50(11) 22_665 10_545 ?
O2 Cu1 O1 167.50(11) . 25_655 ?
O2 Cu1 O1 89.72(13) 22_665 25_655 ?
O1 Cu1 O1 89.26(19) 10_545 25_655 ?
O2 Cu1 O3 98.81(14) . . ?
O2 Cu1 O3 98.81(14) 22_665 . ?
O1 Cu1 O3 93.69(15) 10_545 . ?
O1 Cu1 O3 93.69(15) 25_655 . ?
O2 Cu1 Cu1 84.30(8) . 25_655 ?
O2 Cu1 Cu1 84.29(8) 22_665 25_655 ?
O1 Cu1 Cu1 83.21(8) 10_545 25_655 ?
O1 Cu1 Cu1 83.21(8) 25_655 25_655 ?
O3 Cu1 Cu1 175.63(18) . 25_655 ?
C1 O1 Cu1 123.7(3) . 25_655 ?
C1 O2 Cu1 122.5(3) . . ?
O1 C1 O2 126.2(4) . . ?
O1 C1 C3 117.2(3) . . ?
O2 C1 C3 116.6(3) . . ?
C3 C2 C3 120.8(5) . 24_545 ?
C2 C3 C4 119.7(4) . . ?
C2 C3 C1 120.8(4) . . ?
C4 C3 C1 119.3(3) . . ?
C3 C4 C5 120.7(4) . . ?
C4 C5 C4 118.4(5) . 24_545 ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C6 120.7(3) 24_545 . ?
C7 C6 C7 73.3(10) 24_545 . ?
C7 C6 C8 75.1(7) 24_545 . ?
C7 C6 C8 118.5(7) . . ?
C7 C6 C8 118.5(7) 24_545 24_545 ?
C7 C6 C8 75.1(7) . 24_545 ?
C8 C6 C8 75.7(10) . 24_545 ?
C7 C6 C5 122.9(6) 24_545 . ?
C7 C6 C5 122.9(6) . . ?
C8 C6 C5 118.6(6) . . ?
C8 C6 C5 118.6(6) 24_545 . ?
C6 C7 C8 117.5(9) . 31_645 ?
C6 C7 C9 125.0(10) . . ?
C8 C7 C9 117.4(11) 31_645 . ?
C6 C7 C7 53.3(5) . 24_545 ?
C8 C7 C7 91.8(6) 31_645 24_545 ?
C9 C7 C7 128.3(9) . 24_545 ?
C6 C7 C8 53.3(5) . 24_545 ?
C8 C7 C8 83.2(8) 31_645 24_545 ?
C9 C7 C8 131.0(12) . 24_545 ?
C7 C7 C8 91.5(5) 24_545 24_545 ?
C7 C8 C6 123.6(9) 31_645 . ?
C7 C8 C7 96.7(8) 31_645 24_545 ?
C6 C8 C7 51.5(6) . 24_545 ?
C7 C8 C8 88.2(6) 31_645 24_545 ?
C6 C8 C8 52.1(5) . 24_545 ?
C7 C8 C8 88.5(5) 24_545 24_545 ?
O5 C9 O4 114(2) . . ?
O5 C9 C7 122.5(18) . . ?
O4 C9 C7 120(2) . . ?

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1018379'
