# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_dp
_database_code_depnum_ccdc_archive 'CCDC 1587922'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 Cu2 O10'
_chemical_formula_weight         607.49

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           hexagonal
_symmetry_space_group_name_H-M   P63/mmc

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

_cell_length_a                   18.3886(3)
_cell_length_b                   18.3886(3)
_cell_length_c                   23.7146(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6944.5(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    22928
_cell_measurement_theta_min      0.997
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8113
_exptl_absorpt_correction_T_max  0.9028
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22928
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2402
_reflns_number_gt                1608
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1300P)²+0.0000P] 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         2402
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.006
_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 0.52462(2) 0.04925(4) 0.45479(3) 0.0567(3) Uani 1 2 d S . .
O1 O 0.62867(16) 0.10995(15) 0.49675(10) 0.0607(8) Uani 1 1 d . . .
O2 O 0.58983(16) 0.02696(15) 0.57230(10) 0.0527(7) Uani 1 1 d . . .
O1W O 0.56432(16) 0.1286(3) 0.38229(19) 0.0988(16) Uani 1 2 d S . .
H1WA H 0.5242 0.1090 0.3586 0.119 Uiso 1 1 d R . .
C1 C 0.6416(2) 0.0887(2) 0.54462(14) 0.0481(9) Uani 1 1 d . . .
C2 C 0.7256(2) 0.1435(2) 0.57010(14) 0.0472(9) Uani 1 1 d . . .
C3 C 0.77961(17) 0.22039(17) 0.5454(2) 0.0529(13) Uani 1 2 d S . .
H3A H 0.7628 0.2372 0.5118 0.063 Uiso 1 2 d SR . .
C4 C 0.7497(2) 0.1212(2) 0.62038(14) 0.0502(9) Uani 1 1 d . . .
H4A H 0.7127 0.0683 0.6379 0.060 Uiso 1 1 d R . .
C5 C 0.82678(16) 0.17322(16) 0.64430(19) 0.0471(12) Uani 1 2 d S . .
C6 C 0.85140(16) 0.14860(16) 0.6998(2) 0.0505(13) Uani 1 2 d S . .
C7 C 0.8296(2) 0.1704(2) 0.7500 0.0513(13) Uani 1 4 d S . .
C8 C 0.7817(2) 0.2183(2) 0.7500 0.0513(13) Uani 1 4 d S . .
H8A H 0.7717 0.2283 0.7882 0.062 Uiso 0.50 2 d SPR . .
H8B H 0.8143 0.2713 0.7309 0.062 Uiso 0.25 1 d PR . .
H8C H 0.7291 0.1860 0.7309 0.062 Uiso 0.25 1 d PR . .
C9 C 0.89456(17) 0.10544(17) 0.6979(2) 0.0634(15) Uani 1 2 d S . .
C10 C 0.91906(19) 0.08094(19) 0.6449(3) 0.096(2) Uani 1 2 d S . .
H10A H 0.9004 0.0996 0.6132 0.115 Uiso 1 2 d SR . .
H10B H 0.9791 0.1051 0.6437 0.115 Uiso 1 1 d R . .
C11 C 0.9151(3) 0.0849(3) 0.7500 0.088(3) Uani 1 4 d S . .
H11A H 0.9449 0.0551 0.7500 0.105 Uiso 1 4 calc SR . .

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 0.0749(5) 0.0436(4) 0.0411(4) 0.0000(3) 0.00000(14) 0.0218(2)
O1 0.0699(18) 0.0474(15) 0.0450(15) -0.0035(12) -0.0051(13) 0.0145(13)
O2 0.0581(16) 0.0472(15) 0.0403(14) -0.0031(12) -0.0076(12) 0.0169(13)
O1W 0.118(3) 0.115(4) 0.062(3) 0.040(3) 0.0199(14) 0.057(2)
C1 0.062(2) 0.0408(19) 0.0353(18) -0.0065(16) 0.0009(17) 0.0213(18)
C2 0.054(2) 0.0428(19) 0.0392(18) -0.0035(16) 0.0037(17) 0.0200(17)
C3 0.062(2) 0.062(2) 0.037(3) -0.0043(12) 0.0043(12) 0.033(3)
C4 0.057(2) 0.046(2) 0.046(2) -0.0022(17) 0.0037(18) 0.0248(18)
C5 0.054(2) 0.054(2) 0.036(2) -0.0029(11) 0.0029(11) 0.029(3)
C6 0.049(2) 0.049(2) 0.049(3) 0.0014(12) -0.0014(12) 0.021(2)
C7 0.059(2) 0.059(2) 0.039(3) 0.000 0.000 0.032(3)
C8 0.059(2) 0.059(2) 0.039(3) 0.000 0.000 0.032(3)
C9 0.080(3) 0.080(3) 0.053(3) -0.0020(13) 0.0020(13) 0.058(4)
C10 0.137(5) 0.137(5) 0.072(4) -0.0081(17) 0.0081(17) 0.113(6)
C11 0.112(7) 0.112(7) 0.087(7) 0.000 0.000 0.092(7)

_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 1.939(3) . ?
Cu1 O1 1.939(3) 20_655 ?
Cu1 O2 1.964(2) 8_556 ?
Cu1 O2 1.964(2) 13_656 ?
Cu1 O1W 2.134(4) . ?
Cu1 Cu1 2.6567(13) 13_656 ?
O1 C1 1.261(4) . ?
O2 C1 1.243(4) . ?
O2 Cu1 1.964(2) 13_656 ?
O1W H1WA 0.8496 . ?
C1 C2 1.487(5) . ?
C2 C3 1.386(4) . ?
C2 C4 1.402(5) . ?
C3 C2 1.386(4) 19_665 ?
C3 H3A 0.9598 . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9598 . ?
C5 C4 1.375(4) 19_665 ?
C5 C6 1.531(7) . ?
C6 C9 1.375(7) . ?
C6 C7 1.379(6) . ?
C7 C6 1.379(6) 16_557 ?
C7 C8 1.524(10) . ?
C8 H8A 0.9598 . ?
C8 H8B 0.9642 . ?
C8 H8C 0.9591 . ?
C9 C11 1.397(7) . ?
C9 C10 1.479(8) . ?
C10 H10A 0.9597 . ?
C10 H10B 0.9620 . ?
C11 C9 1.397(7) 16_557 ?
C11 H11A 0.9500 . ?

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 88.66(16) . 20_655 ?
O1 Cu1 O2 88.64(11) . 8_556 ?
O1 Cu1 O2 167.28(11) 20_655 8_556 ?
O1 Cu1 O2 167.28(11) . 13_656 ?
O1 Cu1 O2 88.64(11) 20_655 13_656 ?
O2 Cu1 O2 91.27(16) 8_556 13_656 ?
O1 Cu1 O1W 96.78(13) . . ?
O1 Cu1 O1W 96.78(13) 20_655 . ?
O2 Cu1 O1W 95.88(12) 8_556 . ?
O2 Cu1 O1W 95.88(12) 13_656 . ?
O1 Cu1 Cu1 83.12(8) . 13_656 ?
O1 Cu1 Cu1 83.12(8) 20_655 13_656 ?
O2 Cu1 Cu1 84.21(8) 8_556 13_656 ?
O2 Cu1 Cu1 84.21(8) 13_656 13_656 ?
O1W Cu1 Cu1 179.86(14) . 13_656 ?
C1 O1 Cu1 124.6(2) . . ?
C1 O2 Cu1 122.5(2) . 13_656 ?
Cu1 O1W H1WA 108.3 . . ?
O2 C1 O1 125.6(4) . . ?
O2 C1 C2 117.8(3) . . ?
O1 C1 C2 116.7(3) . . ?
C3 C2 C4 119.1(4) . . ?
C3 C2 C1 119.4(3) . . ?
C4 C2 C1 121.3(3) . . ?
C2 C3 C2 120.4(5) 19_665 . ?
C2 C3 H3A 119.8 19_665 . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C2 120.9(4) . . ?
C5 C4 H4A 119.2 . . ?
C2 C4 H4A 119.9 . . ?
C4 C5 C4 119.4(5) . 19_665 ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C6 120.2(2) 19_665 . ?
C9 C6 C7 122.0(5) . . ?
C9 C6 C5 119.0(5) . . ?
C7 C6 C5 119.0(5) . . ?
C6 C7 C6 119.5(7) 16_557 . ?
C6 C7 C8 120.2(3) 16_557 . ?
C6 C7 C8 120.2(3) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 109.3 . . ?
C7 C8 H8C 109.8 . . ?
H8A C8 H8C 109.4 . . ?
H8B C8 H8C 109.2 . . ?
C6 C9 C11 116.1(6) . . ?
C6 C9 C10 123.6(5) . . ?
C11 C9 C10 120.2(5) . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 110.1 . . ?
C9 C11 C9 124.2(8) 16_557 . ?
C9 C11 H11A 117.9 16_557 . ?
C9 C11 H11A 117.9 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.081

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 -0.035 -0.024 -0.002 4101.1 832.4
_platon_squeeze_details          
; ?
;

####################################################################### 
# 
# 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_dp_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1587923'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 Cu2 O10'
_chemical_formula_weight         607.49

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           hexagonal
_symmetry_space_group_name_H-M   P63/mmc

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

_cell_length_a                   18.4124(3)
_cell_length_b                   18.4124(3)
_cell_length_c                   23.7198(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6964.1(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14401
_cell_measurement_theta_min      0.97
_cell_measurement_theta_max      53.96

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    1.399
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7391
_exptl_absorpt_correction_T_max  0.8613
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14401
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         53.96
_reflns_number_total             2353
_reflns_number_gt                1523
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1200P)²+0.0000P] 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         2353
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52447(2) 0.04895(4) 0.45493(3) 0.0374(3) Uani 1 2 d S . .
O1 O 0.62896(17) 0.11046(17) 0.49631(12) 0.0553(8) Uani 1 1 d . . .
O2 O 0.58938(17) 0.02661(17) 0.57232(11) 0.0498(8) Uani 1 1 d . . .
O1W O 0.56420(17) 0.1284(3) 0.3825(2) 0.0954(18) Uani 1 2 d S . .
H1WA H 0.5241 0.1090 0.3589 0.114 Uiso 1 1 d R . .
C1 C 0.6420(3) 0.0886(2) 0.54493(18) 0.0460(10) Uani 1 1 d . . .
C2 C 0.7251(2) 0.1434(2) 0.57064(16) 0.0420(10) Uani 1 1 d . . .
C3 C 0.77964(19) 0.22036(19) 0.5458(2) 0.0469(14) Uani 1 2 d S . .
H3A H 0.7628 0.2372 0.5122 0.056 Uiso 1 2 d SR . .
C4 C 0.7502(3) 0.1219(2) 0.62017(16) 0.0461(10) Uani 1 1 d . . .
H4A H 0.7132 0.0690 0.6377 0.055 Uiso 1 1 d R . .
C5 C 0.82658(17) 0.17342(17) 0.6432(2) 0.0411(13) Uani 1 2 d S . .
C6 C 0.85082(18) 0.14918(18) 0.7002(2) 0.0480(14) Uani 1 2 d S . .
C7 C 0.8285(3) 0.1715(3) 0.7500 0.0432(13) Uani 1 4 d S . .
C8 C 0.7822(2) 0.2178(2) 0.7500 0.0432(13) Uani 1 4 d S . .
H8A H 0.7722 0.2278 0.7882 0.052 Uiso 0.50 2 d SPR . .
H8B H 0.8148 0.2713 0.7309 0.052 Uiso 0.25 1 d PR . .
H8C H 0.7295 0.1860 0.7309 0.052 Uiso 0.25 1 d PR . .
C9 C 0.89399(19) 0.10601(19) 0.6982(3) 0.0583(17) Uani 1 2 d S . .
C10 C 0.9191(2) 0.0809(2) 0.6449(3) 0.095(3) Uani 1 2 d S . .
H10A H 0.9004 0.0996 0.6131 0.114 Uiso 1 2 d SR . .
H10B H 0.9791 0.1051 0.6437 0.114 Uiso 1 1 d R . .
C11 C 0.9139(3) 0.0861(3) 0.7500 0.090(4) Uani 1 4 d S . .
H11A H 0.9437 0.0563 0.7500 0.108 Uiso 1 4 calc SR . .

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 0.0497(4) 0.0270(4) 0.0278(5) -0.0002(3) -0.00009(16) 0.0135(2)
O1 0.0568(19) 0.0435(17) 0.0454(18) -0.0042(14) -0.0023(15) 0.0100(14)
O2 0.0470(17) 0.0436(16) 0.0437(17) -0.0020(14) -0.0028(14) 0.0113(14)
O1W 0.098(3) 0.111(4) 0.081(4) 0.042(3) 0.0212(17) 0.056(2)
C1 0.056(3) 0.037(2) 0.043(3) -0.0075(19) 0.000(2) 0.021(2)
C2 0.042(2) 0.039(2) 0.041(2) 0.0023(18) 0.0061(18) 0.0172(19)
C3 0.047(2) 0.047(2) 0.043(3) -0.0035(14) 0.0035(14) 0.021(3)
C4 0.053(2) 0.039(2) 0.041(2) -0.0008(19) 0.0022(19) 0.019(2)
C5 0.043(2) 0.043(2) 0.038(3) -0.0001(13) 0.0001(13) 0.021(3)
C6 0.043(2) 0.043(2) 0.050(3) 0.0018(14) -0.0018(14) 0.016(3)
C7 0.048(2) 0.048(2) 0.033(3) 0.000 0.000 0.024(3)
C8 0.048(2) 0.048(2) 0.033(3) 0.000 0.000 0.024(3)
C9 0.072(3) 0.072(3) 0.054(4) -0.0001(15) 0.0001(15) 0.054(4)
C10 0.135(6) 0.135(6) 0.070(5) -0.009(2) 0.009(2) 0.108(7)
C11 0.122(8) 0.122(8) 0.076(8) 0.000 0.000 0.098(9)

_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 1.941(3) 20_655 ?
Cu1 O1 1.941(3) . ?
Cu1 O2 1.957(3) 13_656 ?
Cu1 O2 1.957(3) 8_556 ?
Cu1 O1W 2.134(5) . ?
Cu1 Cu1 2.6471(14) 13_656 ?
O1 C1 1.283(5) . ?
O2 C1 1.249(5) . ?
O2 Cu1 1.957(3) 13_656 ?
O1W H1WA 0.8503 . ?
C1 C2 1.478(6) . ?
C2 C4 1.391(5) . ?
C2 C3 1.393(5) . ?
C3 C2 1.393(5) 19_665 ?
C3 H3A 0.9606 . ?
C4 C5 1.357(5) . ?
C4 H4A 0.9608 . ?
C5 C4 1.357(5) 19_665 ?
C5 C6 1.557(8) . ?
C6 C9 1.378(8) . ?
C6 C7 1.379(7) . ?
C7 C6 1.379(7) 16_557 ?
C7 C8 1.475(11) . ?
C8 H8A 0.9602 . ?
C8 H8B 0.9713 . ?
C8 H8C 0.9592 . ?
C9 C11 1.383(7) . ?
C9 C10 1.497(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9632 . ?
C11 C9 1.383(7) 16_557 ?
C11 H11A 0.9500 . ?

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 88.75(17) 20_655 . ?
O1 Cu1 O2 88.71(12) 20_655 13_656 ?
O1 Cu1 O2 168.08(12) . 13_656 ?
O1 Cu1 O2 168.08(12) 20_655 8_556 ?
O1 Cu1 O2 88.71(12) . 8_556 ?
O2 Cu1 O2 91.38(17) 13_656 8_556 ?
O1 Cu1 O1W 96.14(14) 20_655 . ?
O1 Cu1 O1W 96.14(14) . . ?
O2 Cu1 O1W 95.72(14) 13_656 . ?
O2 Cu1 O1W 95.72(14) 8_556 . ?
O1 Cu1 Cu1 83.66(9) 20_655 13_656 ?
O1 Cu1 Cu1 83.66(9) . 13_656 ?
O2 Cu1 Cu1 84.48(8) 13_656 13_656 ?
O2 Cu1 Cu1 84.48(8) 8_556 13_656 ?
O1W Cu1 Cu1 179.72(19) . 13_656 ?
C1 O1 Cu1 123.9(3) . . ?
C1 O2 Cu1 123.0(3) . 13_656 ?
Cu1 O1W H1WA 108.4 . . ?
O2 C1 O1 125.0(4) . . ?
O2 C1 C2 118.3(4) . . ?
O1 C1 C2 116.7(4) . . ?
C4 C2 C3 118.3(4) . . ?
C4 C2 C1 122.1(4) . . ?
C3 C2 C1 119.6(4) . . ?
C2 C3 C2 120.7(5) 19_665 . ?
C2 C3 H3A 119.6 19_665 . ?
C2 C3 H3A 119.6 . . ?
C5 C4 C2 121.1(4) . . ?
C5 C4 H4A 119.7 . . ?
C2 C4 H4A 119.2 . . ?
C4 C5 C4 120.3(5) . 19_665 ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C6 119.7(3) 19_665 . ?
C9 C6 C7 123.1(6) . . ?
C9 C6 C5 117.8(5) . . ?
C7 C6 C5 119.1(5) . . ?
C6 C7 C6 117.8(8) . 16_557 ?
C6 C7 C8 121.1(4) . . ?
C6 C7 C8 121.1(4) 16_557 . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 109.0 . . ?
C7 C8 H8C 110.3 . . ?
H8A C8 H8C 109.2 . . ?
H8B C8 H8C 108.8 . . ?
C6 C9 C11 115.4(7) . . ?
C6 C9 C10 124.3(6) . . ?
C11 C9 C10 120.3(6) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 110.1 . . ?
C9 C11 C9 125.3(9) 16_557 . ?
C9 C11 H11A 117.3 16_557 . ?
C9 C11 H11A 117.3 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        53.96
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.068

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 -0.042 -0.030 -0.002 4065.7 901.8
_platon_squeeze_details          
; ?
;
