# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_New
_database_code_depnum_ccdc_archive 'CCDC 1510153'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ZJU-12
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H18 Cu2 O12'
_chemical_formula_weight         673.50

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'

_symmetry_cell_setting           trigonal
_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                   18.6401(5)
_cell_length_b                   18.6401(5)
_cell_length_c                   39.7480(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11960.3(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    38107
_cell_measurement_theta_min      1.36
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3060
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'ω 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            38107
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2695
_reflns_number_gt                2262
_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 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. 
;

# 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 -0.055 -0.038 0.003 7414 1770 ' '
_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/[σ²(Fo²)+(0.0653P)²+10.8627P] 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         2695
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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 0.476433(12) 0.95287(2) 0.027388(10) 0.04219(17) Uani 1 2 d S . .
O1 O 0.51856(12) 0.89021(11) 0.00301(5) 0.0592(5) Uani 1 1 d . . .
O2 O 0.55919(13) 0.96967(11) -0.04294(5) 0.0618(5) Uani 1 1 d . . .
O3 O 0.43904(13) 0.8781(3) 0.07159(9) 0.1115(14) Uani 1 2 d S . .
O4 O 0.8090(4) 0.90450(18) -0.09000(14) 0.335(8) Uani 1 2 d S . .
C1 C 0.54907(17) 0.90821(15) -0.02582(7) 0.0508(6) Uani 1 1 d . . .
C2 C 0.57560(17) 0.85279(15) -0.04168(7) 0.0523(6) Uani 1 1 d . . .
C3 C 0.5556(2) 0.77782(12) -0.02623(9) 0.0513(9) Uani 1 2 d S . .
H3A H 0.5289 0.7644 -0.0055 0.062 Uiso 1 2 calc SR . .
C4 C 0.61849(19) 0.87344(17) -0.07224(7) 0.0616(7) Uani 1 1 d . . .
H4A H 0.6319 0.9233 -0.0826 0.074 Uiso 1 1 calc R . .
C5 C 0.6413(3) 0.82066(14) -0.08733(10) 0.0618(10) Uani 1 2 d S . .
C6 C 0.5571(4) 0.77855(18) -0.15324(14) 0.132(3) Uani 1 2 d S . .
H6A H 0.5262 0.7631 -0.1335 0.158 Uiso 1 2 calc SR . .
C7 C 0.6456(3) 0.82278(13) -0.15109(11) 0.0581(10) Uani 1 2 d S . .
C8 C 0.6869(3) 0.84344(15) -0.12010(12) 0.0718(12) Uani 1 2 d S . .
C9 C 0.7706(4) 0.8853(2) -0.12027(15) 0.163(4) Uani 1 2 d S . .
C10 C 0.8155(4) 0.9077(2) -0.15077(16) 0.235(7) Uani 1 2 d S . .
H10A H 0.8731 0.9365 -0.1503 0.282 Uiso 1 2 calc SR . .
C11 C 0.8692(13) 0.9346(6) -0.0817(5) 0.365(12) Uani 1 2 d S . .
H11A H 0.8843 0.9421 -0.0589 0.547 Uiso 1 2 d S . .
H11B H 0.9018 0.9088 -0.0923 0.547 Uiso 0.50 1 d P . .

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 0.0484(2) 0.0343(2) 0.0392(3) 0.00694(16) 0.00347(8) 0.01713(12)
O1 0.0824(13) 0.0498(10) 0.0543(11) 0.0073(8) 0.0139(10) 0.0398(10)
O2 0.0817(13) 0.0547(11) 0.0582(11) 0.0091(9) 0.0160(10) 0.0410(10)
O3 0.127(2) 0.122(3) 0.084(2) 0.063(2) 0.0314(12) 0.0608(16)
O4 0.083(4) 0.657(19) 0.073(3) -0.0012(14) -0.002(3) 0.0417(18)
C1 0.0580(15) 0.0403(13) 0.0526(15) 0.0046(11) 0.0022(12) 0.0234(12)
C2 0.0627(16) 0.0462(14) 0.0498(14) 0.0040(11) 0.0060(12) 0.0285(13)
C3 0.062(2) 0.0512(14) 0.0444(19) 0.0038(8) 0.0075(17) 0.0308(11)
C4 0.0726(18) 0.0540(16) 0.0606(17) 0.0102(13) 0.0110(14) 0.0335(15)
C5 0.072(3) 0.0638(18) 0.052(2) 0.0069(10) 0.014(2) 0.0359(13)
C6 0.077(4) 0.207(7) 0.068(4) 0.0154(16) 0.031(3) 0.0384(19)
C7 0.069(3) 0.0507(14) 0.061(2) 0.0089(10) 0.018(2) 0.0347(13)
C8 0.075(3) 0.075(2) 0.065(3) 0.0088(12) 0.018(2) 0.0377(15)
C9 0.080(4) 0.280(10) 0.063(4) 0.0073(16) 0.015(3) 0.040(2)
C10 0.057(3) 0.450(16) 0.066(4) 0.0080(16) 0.016(3) 0.0287(17)
C11 0.33(2) 0.435(19) 0.296(19) -0.102(9) -0.204(17) 0.164(10)

_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 1.9586(18) 23 ?
Cu1 O1 1.9586(18) . ?
Cu1 O2 1.9665(18) 19_675 ?
Cu1 O2 1.9665(18) 5_675 ?
Cu1 O3 2.132(3) . ?
Cu1 Cu1 2.6563(7) 19_675 ?
O1 C1 1.248(3) . ?
O2 C1 1.263(3) . ?
O2 Cu1 1.9665(18) 19_675 ?
O4 C11 1.026(17) . ?
O4 C9 1.354(8) . ?
C1 C2 1.490(4) . ?
C2 C3 1.396(3) . ?
C2 C4 1.398(4) . ?
C3 C2 1.396(3) 24_565 ?
C4 C5 1.388(3) . ?
C5 C4 1.388(3) 24_565 ?
C5 C8 1.496(6) . ?
C6 C10 1.327(8) 31_664 ?
C6 C7 1.431(7) . ?
C7 C8 1.401(7) . ?
C7 C7 1.414(8) 31_664 ?
C8 C9 1.351(8) . ?
C9 C10 1.413(8) . ?
C10 C6 1.327(8) 31_664 ?

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 88.70(12) 23 . ?
O1 Cu1 O2 89.49(9) 23 19_675 ?
O1 Cu1 O2 167.57(8) . 19_675 ?
O1 Cu1 O2 167.57(8) 23 5_675 ?
O1 Cu1 O2 89.49(9) . 5_675 ?
O2 Cu1 O2 89.63(12) 19_675 5_675 ?
O1 Cu1 O3 96.62(10) 23 . ?
O1 Cu1 O3 96.62(10) . . ?
O2 Cu1 O3 95.80(10) 19_675 . ?
O2 Cu1 O3 95.80(10) 5_675 . ?
O1 Cu1 Cu1 83.71(5) 23 19_675 ?
O1 Cu1 Cu1 83.71(5) . 19_675 ?
O2 Cu1 Cu1 83.88(6) 19_675 19_675 ?
O2 Cu1 Cu1 83.88(6) 5_675 19_675 ?
O3 Cu1 Cu1 179.54(14) . 19_675 ?
C1 O1 Cu1 123.95(17) . . ?
C1 O2 Cu1 123.00(17) . 19_675 ?
C11 O4 C9 136.0(14) . . ?
O1 C1 O2 125.4(2) . . ?
O1 C1 C2 117.8(2) . . ?
O2 C1 C2 116.8(2) . . ?
C3 C2 C4 119.2(3) . . ?
C3 C2 C1 119.6(2) . . ?
C4 C2 C1 121.3(2) . . ?
C2 C3 C2 120.4(3) 24_565 . ?
C5 C4 C2 121.1(3) . . ?
C4 C5 C4 119.1(4) . 24_565 ?
C4 C5 C8 120.45(18) . . ?
C4 C5 C8 120.45(18) 24_565 . ?
C10 C6 C7 122.0(5) 31_664 . ?
C8 C7 C7 122.7(5) . 31_664 ?
C8 C7 C6 121.9(4) . . ?
C7 C7 C6 115.4(5) 31_664 . ?
C9 C8 C7 118.2(5) . . ?
C9 C8 C5 119.7(5) . . ?
C7 C8 C5 122.1(4) . . ?
C8 C9 O4 117.0(5) . . ?
C8 C9 C10 121.2(6) . . ?
O4 C9 C10 121.8(6) . . ?
C6 C10 C9 120.6(6) 31_664 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.050
