# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Cu3DED
_database_code_depnum_ccdc_archive 'CCDC 2152961'
loop_
_audit_author_name
_audit_author_address
'Erik Svensson Grape'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-02-18 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 Cu2 O5'
_chemical_formula_sum            'C15 H8 Cu2 O5'
_chemical_formula_weight         395.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   3.9500(8)
_cell_length_b                   29.930(6)
_cell_length_c                   12.040(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.96(3)
_cell_angle_gamma                90
_cell_volume                     1421.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25475
_cell_measurement_theta_min      0.064
_cell_measurement_theta_max      0.899

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  'JEOL JEM 2100-LaB6'
_diffrn_measurement_method       'continuous rotation'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25475
_diffrn_reflns_av_unetI/netI     0.1152
_diffrn_reflns_av_R_equivalents  0.1992
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.064
_diffrn_reflns_theta_max         0.899
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measured_fraction_theta_full 0.867
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_Laue_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.867
_reflns_number_total             2486
_reflns_number_gt                2279
_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.

 _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       
;
Stef Smeets, Bin Wang, Magdalena O. Cichocka, Jonas Angstrom, Wei Wan.
(2018, April 11). Instamatic (Version 0.6). Zenodo.
http://doi.org/10.5281/zenodo.1217026
;
_computing_cell_refinement       
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_data_reduction        
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1538P)²+1.6297P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       1942(35)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2486
_refine_ls_number_parameters     200
_refine_ls_number_restraints     160
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.1854
_refine_ls_wR_factor_ref         0.4459
_refine_ls_wR_factor_gt          0.4404
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.005
_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 0.7660(13) 0.50917(17) 0.8653(3) 0.0545(13) Uani 1 1 d . . . . .
Cu2 Cu 0.2323(12) 0.47593(17) 0.7107(3) 0.0538(13) Uani 1 1 d . . . . .
C1 C 0.511(3) 0.5622(5) 0.6747(8) 0.040(3) Uani 1 1 d . . . . .
C2 C 0.522(2) 0.6059(4) 0.6086(7) 0.031(3) Uani 1 1 d . . . . .
C3 C 0.382(2) 0.6078(4) 0.4925(7) 0.0309(16) Uani 1 1 d . U . . .
H3 H 0.293391 0.582259 0.457871 0.037 Uiso 1 1 calc R U . . .
C4 C 0.386(3) 0.6506(4) 0.4324(7) 0.037(3) Uani 1 1 d . . . . .
H4 H 0.294764 0.651896 0.359694 0.045 Uiso 1 1 calc R U . . .
C5 C 0.530(2) 0.6910(4) 0.4839(7) 0.0300(14) Uani 1 1 d D U . . .
C6 C 0.682(2) 0.6876(4) 0.5987(7) 0.0305(14) Uani 1 1 d . U . . .
H6 H 0.782566 0.712630 0.632144 0.037 Uiso 1 1 calc R U . . .
C7 C 0.677(2) 0.6464(4) 0.6589(7) 0.0305(16) Uani 1 1 d . U . . .
H7 H 0.773805 0.645095 0.730985 0.037 Uiso 1 1 calc R U . . .
C8 C 0.529(3) 0.7348(3) 0.4139(6) 0.0299(14) Uani 1 1 d D U . . .
C9 C 0.549(2) 0.7813(4) 0.4723(7) 0.0297(14) Uani 1 1 d D U . . .
C10 C 0.679(3) 0.8185(4) 0.4111(7) 0.033(3) Uani 1 1 d . . . . .
H10 H 0.772515 0.813834 0.342659 0.039 Uiso 1 1 calc R U . . .
C11 C 0.664(3) 0.8629(4) 0.4573(7) 0.033(3) Uani 1 1 d . . . . .
H11 H 0.740326 0.887012 0.416603 0.040 Uiso 1 1 calc R U . . .
C12 C 0.533(3) 0.8707(4) 0.5640(7) 0.0306(16) Uani 1 1 d D U . . .
C13 C 0.394(3) 0.8341(4) 0.6251(7) 0.0309(15) Uani 1 1 d . U . . .
H13 H 0.293430 0.839232 0.692107 0.037 Uiso 1 1 calc R U . . .
C14 C 0.412(2) 0.7893(4) 0.5811(7) 0.0307(14) Uani 1 1 d . U . . .
H14 H 0.336228 0.765412 0.622257 0.037 Uiso 1 1 calc R U . . .
C15 C 0.518(3) 0.9179(4) 0.6154(7) 0.0324(17) Uani 1 1 d D U . . .
O1 O 0.662(3) 0.5635(4) 0.7764(7) 0.048(3) Uani 1 1 d . . . . .
O2 O 0.351(3) 0.5279(4) 0.6285(7) 0.047(3) Uani 1 1 d . . . . .
O3 O 0.516(3) 0.7329(4) 0.3092(7) 0.057(3) Uani 1 1 d D . . . .
O4 O 0.632(3) 0.9515(4) 0.5582(7) 0.055(3) Uani 1 1 d . . . . .
O5 O 0.376(3) 0.9211(4) 0.7142(8) 0.054(3) Uani 1 1 d . . . . .


_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 1.978(11) . ?
Cu1 O4 1.987(13) 2_646 ?
Cu2 O2 1.915(11) . ?
Cu2 O5 1.930(11) 2_546 ?
C1 O2 1.315(17) . ?
C1 O1 1.334(14) . ?
C1 C2 1.531(15) . ?
C2 C3 1.476(12) . ?
C2 C7 1.475(16) . ?
C3 C4 1.472(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.462(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.482(12) . ?
C5 C8 1.558(12) . ?
C6 C7 1.432(16) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.261(10) . ?
C8 C9 1.558(12) . ?
C9 C10 1.445(15) . ?
C9 C14 1.462(12) . ?
C10 C11 1.445(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.429(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.446(15) . ?
C12 C15 1.544(13) . ?
C13 C14 1.443(15) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O4 1.312(16) . ?
C15 O5 1.345(13) . ?

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 O4 174.8(5) . 2_646 ?
O2 Cu2 O5 176.2(5) . 2_546 ?
O2 C1 O1 126.3(10) . . ?
O2 C1 C2 118.2(9) . . ?
O1 C1 C2 115.5(11) . . ?
C3 C2 C7 119.0(9) . . ?
C3 C2 C1 120.4(10) . . ?
C7 C2 C1 120.6(9) . . ?
C4 C3 C2 119.1(9) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 121.7(8) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.9(9) . . ?
C4 C5 C8 118.5(8) . . ?
C6 C5 C8 123.5(9) . . ?
C7 C6 C5 121.1(9) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 121.1(8) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O3 C8 C9 119.3(8) . . ?
O3 C8 C5 120.1(8) . . ?
C9 C8 C5 120.5(7) . . ?
C10 C9 C14 119.1(9) . . ?
C10 C9 C8 117.9(8) . . ?
C14 C9 C8 122.7(9) . . ?
C9 C10 C11 119.4(8) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.4(10) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.9(9) . . ?
C11 C12 C15 122.2(9) . . ?
C13 C12 C15 117.8(8) . . ?
C14 C13 C12 119.3(8) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 120.7(10) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
O4 C15 O5 125.4(11) . . ?
O4 C15 C12 118.0(9) . . ?
O5 C15 C12 116.6(9) . . ?
C1 O1 Cu1 123.0(9) . . ?
C1 O2 Cu2 122.8(7) . . ?
C15 O4 Cu1 119.3(7) . 2_656 ?
C15 O5 Cu2 126.0(9) . 2_556 ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.047



# start Validation Reply Form
_vrf_RINTA01_Cu3DED              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The data is likely to contain effects of dynamical effects (multiple
scattering), leading to slightly elevated R-values.
;
_vrf_PLAT020_Cu3DED              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.199 Report
RESPONSE: The data is likely to contain effects of dynamical effects (multiple
scattering), leading to slightly elevated R-values.
;
_vrf_PLAT082_Cu3DED              
;
PROBLEM: High R1 Value ..................................       0.19 Report
RESPONSE: The data is likely to contain effects of dynamical effects (multiple
scattering), leading to slightly elevated R-values.
;
_vrf_PLAT084_Cu3DED              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.45 Report
RESPONSE: The data is likely to contain effects of dynamical effects (multiple
scattering), leading to slightly elevated R-values.
;
# end Validation Reply Form
