# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1944353'
loop_
_audit_author_name
_audit_author_address
'Ruiqing Fan'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2019-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Cu2 O9'
_chemical_formula_weight         563.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.0119(2)
_cell_length_b                   25.5207(3)
_cell_length_c                   5.78740(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9520(10)
_cell_angle_gamma                90.00
_cell_volume                     2627.92(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      68.20

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_T_max  0.576
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6122
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         68.20
_reflns_number_total             2398
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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. 
;

_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)+(0.1273P)²+2.8861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2398
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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 0.91706(2) 0.478084(14) 0.04900(7) 0.0228(3) Uani 1 1 d . . .
O1 O 0.86917(13) 0.54616(9) -0.0063(4) 0.0349(5) Uani 1 1 d . . .
O2 O 0.83264(12) 0.44517(9) -0.1533(4) 0.0338(5) Uani 1 1 d . . .
O3 O 0.95922(12) 0.40820(7) 0.0824(4) 0.0293(5) Uani 1 1 d . . .
O4 O 1.0000 0.50911(11) 0.2500 0.0213(6) Uani 1 2 d S . .
H4A H 1.0000 0.5420 0.2500 0.032 Uiso 1 2 d SR . .
O5 O 0.91191(14) 0.21494(8) -0.0876(5) 0.0418(6) Uani 1 1 d . . .
C1 C 1.0000 0.38606(15) 0.2500 0.0227(8) Uani 1 2 d S . .
C2 C 1.0000 0.32717(15) 0.2500 0.0233(8) Uani 1 2 d S . .
C3 C 0.95493(15) 0.30063(11) 0.0688(5) 0.0271(6) Uani 1 1 d . . .
H3A H 0.9257 0.3189 -0.0515 0.032 Uiso 1 1 calc R . .
C4 C 0.95499(16) 0.24607(11) 0.0735(5) 0.0284(7) Uani 1 1 d . . .
C5 C 1.0000 0.21883(16) 0.2500 0.0310(10) Uani 1 2 d S . .
H5A H 1.0000 0.1824 0.2500 0.037 Uiso 1 2 calc SR . .
C6 C 0.86165(19) 0.23938(12) -0.2730(6) 0.0357(7) Uani 1 1 d . . .
H6A H 0.8892 0.2537 -0.3896 0.043 Uiso 1 1 calc R . .
H6B H 0.8339 0.2675 -0.2124 0.043 Uiso 1 1 calc R . .
C7 C 0.80911(17) 0.19675(12) -0.3770(6) 0.0309(7) Uani 1 1 d . . .
C8 C 0.7529(2) 0.17959(14) -0.2579(6) 0.0408(8) Uani 1 1 d . . .
H8A H 0.7454 0.1965 -0.1210 0.049 Uiso 1 1 calc R . .
C9 C 0.7926(2) 0.36226(14) -0.6616(6) 0.0394(8) Uani 1 1 d . . .
H9A H 0.8290 0.3741 -0.7468 0.047 Uiso 1 1 calc R . .
C10 C 0.78369(16) 0.38661(11) -0.4533(5) 0.0283(6) Uani 1 1 d . . .
C11 C 0.7298(2) 0.36804(15) -0.3283(6) 0.0399(8) Uani 1 1 d . . .
H11A H 0.7246 0.3833 -0.1856 0.048 Uiso 1 1 calc R . .
C12 C 0.8169(2) 0.17331(15) -0.5855(6) 0.0407(8) Uani 1 1 d . . .
H12A H 0.8536 0.1851 -0.6696 0.049 Uiso 1 1 calc R . .
C13 C 0.83225(16) 0.43201(11) -0.3644(5) 0.0279(6) 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 0.0217(4) 0.0166(3) 0.0252(4) -0.00190(13) -0.0119(2) 0.00146(13)
O1 0.0349(12) 0.0267(12) 0.0381(12) 0.0035(9) -0.0096(10) 0.0111(9)
O2 0.0256(10) 0.0332(12) 0.0376(13) -0.0086(9) -0.0112(9) -0.0057(9)
O3 0.0351(11) 0.0143(10) 0.0317(11) -0.0014(7) -0.0163(9) 0.0023(8)
O4 0.0242(13) 0.0133(11) 0.0217(13) 0.000 -0.0111(11) 0.000
O5 0.0406(13) 0.0180(10) 0.0553(15) -0.0058(9) -0.0288(11) -0.0053(9)
C1 0.0193(17) 0.0168(18) 0.028(2) 0.000 -0.0076(14) 0.000
C2 0.0179(17) 0.0149(18) 0.033(2) 0.000 -0.0100(15) 0.000
C3 0.0224(13) 0.0176(14) 0.0355(16) 0.0003(11) -0.0135(12) -0.0017(10)
C4 0.0218(13) 0.0178(14) 0.0403(18) -0.0039(11) -0.0120(13) -0.0039(10)
C5 0.025(2) 0.0131(18) 0.050(3) 0.000 -0.0088(18) 0.000
C6 0.0326(16) 0.0261(15) 0.0413(18) -0.0005(13) -0.0162(13) -0.0095(13)
C7 0.0289(14) 0.0248(15) 0.0334(16) -0.0007(12) -0.0126(12) -0.0097(11)
C8 0.048(2) 0.0373(18) 0.0345(18) -0.0110(14) -0.0007(15) -0.0174(16)
C9 0.0394(18) 0.0414(19) 0.0367(18) -0.0082(14) 0.0039(14) -0.0191(15)
C10 0.0247(13) 0.0244(14) 0.0302(15) -0.0024(11) -0.0129(11) -0.0072(12)
C11 0.0409(18) 0.044(2) 0.0334(17) -0.0111(14) 0.0003(14) -0.0183(15)
C12 0.0373(17) 0.043(2) 0.0406(19) -0.0067(14) 0.0020(15) -0.0204(15)
C13 0.0208(13) 0.0227(14) 0.0350(16) -0.0019(12) -0.0121(11) -0.0041(11)

_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 O4 1.9160(12) . ?
Cu1 O3 1.9363(19) . ?
Cu1 O1 1.944(2) . ?
Cu1 O2 1.958(2) . ?
O1 C13 1.264(4) 6_566 ?
O2 C13 1.266(4) . ?
O3 C1 1.256(3) . ?
O4 Cu1 1.9160(12) 2_755 ?
O5 C4 1.370(3) . ?
O5 C6 1.434(4) . ?
C1 O3 1.256(3) 2_755 ?
C1 C2 1.503(5) . ?
C2 C3 1.397(3) . ?
C2 C3 1.397(3) 2_755 ?
C3 C4 1.393(4) . ?
C4 C5 1.388(4) . ?
C5 C4 1.388(4) 2_755 ?
C6 C7 1.505(4) . ?
C7 C12 1.373(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.381(5) 7_654 ?
C9 C8 1.381(5) 7_654 ?
C9 C10 1.387(5) . ?
C10 C11 1.382(5) . ?
C10 C13 1.494(4) . ?
C11 C12 1.392(5) 7_654 ?
C12 C11 1.392(5) 7_654 ?
C13 O1 1.264(4) 6_565 ?

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
O4 Cu1 O3 93.64(10) . . ?
O4 Cu1 O1 90.84(10) . . ?
O3 Cu1 O1 175.35(9) . . ?
O4 Cu1 O2 178.96(10) . . ?
O3 Cu1 O2 85.45(9) . . ?
O1 Cu1 O2 90.08(9) . . ?
C13 O1 Cu1 123.5(2) 6_566 . ?
C13 O2 Cu1 125.3(2) . . ?
C1 O3 Cu1 131.7(2) . . ?
Cu1 O4 Cu1 131.18(15) 2_755 . ?
C4 O5 C6 118.8(2) . . ?
O3 C1 O3 126.5(4) . 2_755 ?
O3 C1 C2 116.74(18) . . ?
O3 C1 C2 116.74(18) 2_755 . ?
C3 C2 C3 122.0(4) . 2_755 ?
C3 C2 C1 118.99(18) . . ?
C3 C2 C1 119.00(18) 2_755 . ?
C4 C3 C2 118.1(3) . . ?
O5 C4 C5 114.5(3) . . ?
O5 C4 C3 124.6(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C4 119.9(4) . 2_755 ?
O5 C6 C7 105.6(2) . . ?
C12 C7 C8 118.9(3) . . ?
C12 C7 C6 121.5(3) . . ?
C8 C7 C6 119.6(3) . . ?
C9 C8 C7 121.2(3) 7_654 . ?
C8 C9 C10 119.8(3) 7_654 . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 C13 120.5(3) . . ?
C9 C10 C13 120.4(3) . . ?
C10 C11 C12 120.4(3) . 7_654 ?
C7 C12 C11 120.5(3) . 7_654 ?
O1 C13 O2 125.9(3) 6_565 . ?
O1 C13 C10 117.2(3) 6_565 . ?
O2 C13 C10 117.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        68.20
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.172

# SQUEEZE RESULTS
# 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 0.000 0.000 -0.046 348 84 ' '
2 0.500 0.500 0.035 348 84 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
