# Electronic Supplementary Material (ESI) for ChemComm.
# 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_D:\wmy\Hufl\CU-DAT~2\xray\useful\platon_sq
_database_code_depnum_ccdc_archive 'CCDC 1586943'
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2019-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Cu2 O12'
_chemical_formula_weight         638.48

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'
Cu Cu -1.9646 0.5888 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           129
_space_group_name_H-M_alt        'P 4/n m m'
_space_group_name_Hall           '-P 4a 2a'

_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+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'x+1/2, -y, -z'
'-x, y+1/2, -z'
'y+1/2, x+1/2, -z'
'-y, -x, -z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'
'-x-1/2, y, z'
'x, -y-1/2, z'
'-y-1/2, -x-1/2, z'
'y, x, z'

_cell_length_a                   18.9546(5)
_cell_length_b                   18.9546(5)
_cell_length_c                   13.4969(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4849.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3589
_cell_measurement_theta_min      3.9880
_cell_measurement_theta_max      72.4840

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.875
_exptl_crystal_F_000             1292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    1.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            13690
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.021
_diffrn_reflns_theta_max         73.250
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2670
_reflns_number_gt                1806
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1135P)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         2670
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.001

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 0.46655(3) 0.46655(3) 0.42690(5) 0.0370(2) Uani 1 2 d S T P . .
O1 O 0.37975(14) 0.48214(14) 0.50238(18) 0.0508(7) Uani 1 1 d . . . . .
O2 O 0.43675(14) 0.54077(15) 0.62380(18) 0.0497(7) Uani 1 1 d . . . . .
O3 O 0.4163(2) 0.4163(2) 0.3008(3) 0.102(2) Uani 1 2 d S T P . .
O4 O 0.250000 0.62343(19) 0.9434(2) 0.0481(9) Uani 1 2 d S T P . .
C1 C 0.3829(2) 0.5190(2) 0.5812(3) 0.0432(8) Uani 1 1 d . . . . .
C2 C 0.31317(19) 0.53932(19) 0.6247(2) 0.0411(8) Uani 1 1 d . . . . .
C3 C 0.250000 0.5141(3) 0.5890(3) 0.0420(11) Uani 1 2 d S T P . .
H3 H 0.250000 0.478812 0.539059 0.050 Uiso 1 2 calc R U P . .
C4 C 0.31298(19) 0.5924(2) 0.6960(2) 0.0415(8) Uani 1 1 d . . . . .
H4 H 0.356479 0.610414 0.720136 0.050 Uiso 1 1 calc R U . . .
C5 C 0.250000 0.6193(3) 0.7320(3) 0.0372(10) Uani 1 2 d S T P . .
C6 C 0.250000 0.6862(2) 0.7901(3) 0.0345(10) Uani 1 2 d S T P . .
C7 C 0.250000 0.750000 0.7381(4) 0.0359(14) Uani 1 4 d S T P . .
C8 C 0.250000 0.750000 0.6259(4) 0.0474(17) Uani 1 4 d S T P . .
H8A H 0.292779 0.726632 0.601703 0.071 Uiso 0.25 1 calc R U P . .
H8B H 0.248848 0.798732 0.601703 0.071 Uiso 0.5 2 calc R U P . .
H8C H 0.208373 0.724636 0.601703 0.071 Uiso 0.25 1 calc R U P . .
C9 C 0.250000 0.6870(3) 0.8936(3) 0.0383(10) Uani 1 2 d S T P . .
C10 C 0.250000 0.750000 0.9447(4) 0.0364(14) Uani 1 4 d S T P . .
C11 C 0.1858(5) 0.5940(5) 0.9621(5) 0.061(2) Uani 0.5 1 d . . P . .
H11A H 0.191932 0.551540 1.002623 0.092 Uiso 0.5 1 calc R U P . .
H11B H 0.163021 0.581347 0.899385 0.092 Uiso 0.5 1 calc R U P . .
H11C H 0.156198 0.627957 0.997784 0.092 Uiso 0.5 1 calc R U 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 O1 1.957(3) 16 ?
Cu1 O1 1.957(3) . ?
Cu1 O2 1.961(3) 8_666 ?
Cu1 O2 1.961(3) 9_666 ?
Cu1 O3 2.170(4) . ?
Cu1 Cu1 2.6663(12) 9_666 ?
O1 C1 1.275(4) . ?
O2 C1 1.242(4) . ?
O4 C11 1.363(9) 13_655 ?
O4 C11 1.363(9) . ?
O4 C9 1.379(6) . ?
C1 C2 1.496(5) . ?
C2 C3 1.376(4) . ?
C2 C4 1.392(5) . ?
C4 C5 1.386(4) . ?
C5 C6 1.491(6) . ?
C6 C9 1.397(6) . ?
C6 C7 1.397(5) . ?
C7 C8 1.514(8) . ?
C9 C10 1.380(6) . ?
C10 C10 1.492(10) 10_567 ?

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 89.02(17) 16 . ?
O1 Cu1 O2 167.86(10) 16 8_666 ?
O1 Cu1 O2 88.91(12) . 8_666 ?
O1 Cu1 O2 88.92(12) 16 9_666 ?
O1 Cu1 O2 167.86(10) . 9_666 ?
O2 Cu1 O2 90.60(17) 8_666 9_666 ?
O1 Cu1 O3 96.07(13) 16 . ?
O1 Cu1 O3 96.07(13) . . ?
O2 Cu1 O3 96.04(13) 8_666 . ?
O2 Cu1 O3 96.04(13) 9_666 . ?
O1 Cu1 Cu1 86.72(7) 16 9_666 ?
O1 Cu1 Cu1 86.72(7) . 9_666 ?
O2 Cu1 Cu1 81.22(7) 8_666 9_666 ?
O2 Cu1 Cu1 81.22(7) 9_666 9_666 ?
O3 Cu1 Cu1 176.08(17) . 9_666 ?
C1 O1 Cu1 118.6(2) . . ?
C1 O2 Cu1 125.7(2) . 9_666 ?
C11 O4 C11 126.6(9) 13_655 . ?
C11 O4 C9 116.6(4) 13_655 . ?
C11 O4 C9 116.6(4) . . ?
O2 C1 O1 127.3(3) . . ?
O2 C1 C2 117.4(3) . . ?
O1 C1 C2 115.3(3) . . ?
C3 C2 C4 119.4(3) . . ?
C3 C2 C1 122.8(3) . . ?
C4 C2 C1 117.3(3) . . ?
C2 C3 C2 120.9(5) 13_655 . ?
C5 C4 C2 120.7(3) . . ?
C4 C5 C4 118.9(4) 13_655 . ?
C4 C5 C6 119.8(2) 13_655 . ?
C4 C5 C6 119.8(2) . . ?
C9 C6 C7 119.6(4) . . ?
C9 C6 C5 122.3(4) . . ?
C7 C6 C5 118.2(4) . . ?
C6 C7 C6 119.7(5) 3_565 . ?
C6 C7 C8 120.1(3) 3_565 . ?
C6 C7 C8 120.1(3) . . ?
O4 C9 C10 120.8(4) . . ?
O4 C9 C6 118.6(4) . . ?
C10 C9 C6 120.6(4) . . ?
C9 C10 C9 120.0(5) . 3_565 ?
C9 C10 C10 120.0(3) . 10_567 ?
C9 C10 C10 120.0(3) 3_565 10_567 ?

_refine_diff_density_max         0.785
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.077



