# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1529129'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Cu2 N O10'
_chemical_formula_weight         580.43

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'
N N 0.0311 0.0180 '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           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'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -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'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'y+2/3, x+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'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, 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'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-y+2/3, -x+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'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'

_cell_length_a                   18.6153(7)
_cell_length_b                   18.6153(7)
_cell_length_c                   38.3750(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11516.5(7)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14559
_cell_measurement_theta_min      0.986
_cell_measurement_theta_max      73.91

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2628
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7433
_exptl_absorpt_correction_T_max  0.8532
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\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            14559
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         73.91
_reflns_number_total             2816
_reflns_number_gt                2483
_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)+(0.1091P)²+22.2311P] 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         2816
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1762
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_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
C1 C 0.36019(17) 0.45241(18) 0.47354(6) 0.0380(6) Uani 1 1 d . . .
C2 C 0.27935(17) 0.42990(18) 0.45642(7) 0.0394(6) Uani 1 1 d . C .
C3 C 0.22258(12) 0.4452(2) 0.47340(10) 0.0385(8) Uani 1 2 d S . .
H3 H 0.2328 0.4655 0.4961 0.046 Uiso 1 2 calc SR C .
C4 C 0.26413(18) 0.3996(2) 0.42277(7) 0.0462(7) Uani 1 1 d . . .
H4 H 0.3021 0.3888 0.4116 0.055 Uiso 1 1 calc R C .
C5 C 0.19250(15) 0.3850(3) 0.40543(11) 0.0476(11) Uani 1 2 d S . .
C6 C 0.17788(17) 0.3558(3) 0.36822(11) 0.0515(11) Uani 1 2 d S . .
C7 C 0.1834(5) 0.2883(5) 0.35812(16) 0.0622(19) Uani 0.50 1 d PD . .
H7A H 0.1930 0.2543 0.3752 0.075 Uiso 0.25 1 d PR A 1
N1 N 0.1933(7) 0.2272(6) 0.3839(2) 0.047(2) Uani 0.25 1 d PD B 2
H1A H 0.1883 0.1783 0.3777 0.056 Uiso 0.25 1 d PR B 2
H1B H 0.1999 0.2424 0.4065 0.056 Uiso 0.25 1 d PR B 2
C8 C 0.1734(4) 0.2674(5) 0.32267(16) 0.0582(18) Uani 0.50 1 d P . .
H8A H 0.1804 0.2226 0.3144 0.070 Uiso 0.50 1 d PR C .
Cu1 Cu 0.523482(14) 0.476518(14) 0.471621(11) 0.0289(2) Uani 1 2 d S . .
O1 O 0.41087(13) 0.44161(15) 0.45604(5) 0.0476(5) Uani 1 1 d . C -1
O2 O 0.37108(12) 0.48173(14) 0.50392(5) 0.0440(5) Uani 1 1 d . . -1
O1W O 0.55824(15) 0.44176(15) 0.42370(11) 0.0926(15) Uani 1 2 d S C .

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
C1 0.0437(14) 0.0473(14) 0.0332(12) -0.0003(11) -0.0019(10) 0.0304(12)
C2 0.0413(15) 0.0507(15) 0.0342(13) -0.0037(11) -0.0035(11) 0.0291(12)
C3 0.0391(14) 0.046(2) 0.0325(17) -0.0005(15) -0.0002(8) 0.0232(10)
C4 0.0424(15) 0.0669(19) 0.0395(14) -0.0110(13) -0.0037(11) 0.0349(15)
C5 0.0452(15) 0.071(3) 0.035(2) -0.0133(18) -0.0066(9) 0.0357(15)
C6 0.0453(14) 0.082(3) 0.039(2) -0.019(2) -0.0095(11) 0.0412(16)
C7 0.068(4) 0.103(6) 0.041(3) -0.022(4) -0.014(3) 0.062(4)
N1 0.070(6) 0.061(6) 0.024(4) -0.021(4) -0.018(4) 0.044(6)
C8 0.062(4) 0.092(5) 0.040(3) -0.022(3) -0.012(3) 0.053(4)
Cu1 0.0385(3) 0.0385(3) 0.0210(3) -0.00056(8) 0.00056(8) 0.0278(2)
O1 0.0446(11) 0.0748(14) 0.0393(9) -0.0125(10) -0.0081(8) 0.0416(11)
O2 0.0424(10) 0.0626(12) 0.0348(9) -0.0088(9) -0.0056(8) 0.0320(10)
O1W 0.097(2) 0.097(2) 0.072(2) -0.0350(13) 0.0350(13) 0.040(3)

_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
C1 O1 1.254(3) . ?
C1 O2 1.260(3) . ?
C1 C2 1.497(4) . ?
C2 C4 1.381(4) . ?
C2 C3 1.386(3) . ?
C3 C2 1.386(3) 22 ?
C4 C5 1.390(3) . ?
C5 C4 1.390(3) 22 ?
C5 C6 1.504(6) . ?
C6 C7 1.366(8) 22 ?
C6 C7 1.366(8) . ?
C6 C8 1.379(8) 31 ?
C6 C8 1.379(8) 16 ?
C7 C8 1.402(8) . ?
C7 C7 1.461(14) 22 ?
C7 N1 1.586(10) . ?
C7 C8 1.869(12) 16 ?
C7 C8 2.030(9) 22 ?
C8 C6 1.379(8) 31 ?
C8 C8 1.477(12) 22 ?
C8 C7 1.869(12) 16 ?
C8 C7 2.030(9) 22 ?
Cu1 O1 1.9524(19) . ?
Cu1 O1 1.9524(19) 24_665 ?
Cu1 O2 1.9525(19) 19_666 ?
Cu1 O2 1.9525(19) 6_556 ?
Cu1 O1W 2.154(3) . ?
Cu1 Cu1 2.6527(9) 19_666 ?
O2 Cu1 1.9525(19) 19_666 ?

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 C1 O2 126.5(3) . . ?
O1 C1 C2 116.9(2) . . ?
O2 C1 C2 116.7(2) . . ?
C4 C2 C3 120.1(3) . . ?
C4 C2 C1 119.8(2) . . ?
C3 C2 C1 119.9(2) . . ?
C2 C3 C2 119.7(3) . 22 ?
C2 C4 C5 120.5(3) . . ?
C4 C5 C4 119.0(4) 22 . ?
C4 C5 C6 120.50(18) 22 . ?
C4 C5 C6 120.50(18) . . ?
C7 C6 C7 64.6(7) 22 . ?
C7 C6 C8 85.8(5) 22 31 ?
C7 C6 C8 120.0(5) . 31 ?
C7 C6 C8 120.0(5) 22 16 ?
C7 C6 C8 85.8(5) . 16 ?
C8 C6 C8 64.8(6) 31 16 ?
C7 C6 C5 121.3(4) 22 . ?
C7 C6 C5 121.3(4) . . ?
C8 C6 C5 118.7(4) 31 . ?
C8 C6 C5 118.7(4) 16 . ?
C6 C7 C8 118.1(6) . . ?
C6 C7 C7 57.7(3) . 22 ?
C8 C7 C7 90.3(4) . 22 ?
C6 C7 N1 124.8(6) . . ?
C8 C7 N1 116.9(6) . . ?
C7 C7 N1 118.3(5) 22 . ?
C6 C7 C8 47.4(4) . 16 ?
C8 C7 C8 87.1(6) . 16 ?
C7 C7 C8 90.3(3) 22 16 ?
N1 C7 C8 140.6(6) . 16 ?
C6 C7 C8 86.3(4) . 22 ?
C8 C7 C8 46.7(4) . 22 ?
C7 C7 C8 43.7(2) 22 22 ?
N1 C7 C8 131.1(7) . 22 ?
C8 C7 C8 88.2(4) 16 22 ?
C6 C8 C7 121.9(6) 31 . ?
C6 C8 C8 57.6(3) 31 22 ?
C7 C8 C8 89.7(4) . 22 ?
C6 C8 C7 46.8(4) 31 16 ?
C7 C8 C7 92.9(6) . 16 ?
C8 C8 C7 89.7(3) 22 16 ?
C6 C8 C7 88.8(4) 31 22 ?
C7 C8 C7 46.0(5) . 22 ?
C8 C8 C7 43.7(2) 22 22 ?
C7 C8 C7 91.8(4) 16 22 ?
O1 Cu1 O1 89.38(14) . 24_665 ?
O1 Cu1 O2 167.98(8) . 19_666 ?
O1 Cu1 O2 89.49(10) 24_665 19_666 ?
O1 Cu1 O2 89.49(10) . 6_556 ?
O1 Cu1 O2 167.98(8) 24_665 6_556 ?
O2 Cu1 O2 89.13(13) 19_666 6_556 ?
O1 Cu1 O1W 94.15(12) . . ?
O1 Cu1 O1W 94.15(12) 24_665 . ?
O2 Cu1 O1W 97.87(12) 19_666 . ?
O2 Cu1 O1W 97.87(12) 6_556 . ?
O1 Cu1 Cu1 83.41(6) . 19_666 ?
O1 Cu1 Cu1 83.41(6) 24_665 19_666 ?
O2 Cu1 Cu1 84.58(6) 19_666 19_666 ?
O2 Cu1 Cu1 84.58(6) 6_556 19_666 ?
O1W Cu1 Cu1 176.55(15) . 19_666 ?
C1 O1 Cu1 123.47(18) . . ?
C1 O2 Cu1 121.95(18) . 19_666 ?

# 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 -0.045 -0.029 -0.002 6981 1920 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        73.91
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1529130'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 Cu2 N O12'
_chemical_formula_weight         610.43

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_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, -x+y, -z'
'x-y, -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+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   18.555(3)
_cell_length_b                   18.555(3)
_cell_length_c                   38.688(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11535(3)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    77586
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2753
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8332
_exptl_absorpt_correction_T_max  0.9189
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            77586
_diffrn_reflns_av_R_equivalents  0.1629
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3259
_reflns_number_gt                2420
_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)+(0.1000P)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         3259
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.005

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 0.523960(14) 0.476040(14) -0.028007(13) 0.0368(2) Uani 1 2 d S . .
O1 O 0.48161(15) 0.37136(14) -0.00291(6) 0.0493(6) Uani 1 1 d . . .
O2 O 0.44086(17) 0.41067(15) 0.04439(6) 0.0539(7) Uani 1 1 d . . .
O7 O 0.55992(16) 0.44008(16) -0.07466(13) 0.1110(19) Uani 1 2 d S . .
C1 C 0.4527(2) 0.3607(2) 0.02737(9) 0.0445(8) Uani 1 1 d . . .
C2 C 0.4312(2) 0.2807(2) 0.04421(9) 0.0453(8) Uani 1 1 d . . .
C3 C 0.4006(2) 0.2648(2) 0.07796(9) 0.0545(9) Uani 1 1 d . . .
H3 H 0.3903 0.3030 0.0892 0.065 Uiso 1 1 calc R . .
C4 C 0.3855(4) 0.19273(18) 0.09490(14) 0.0558(14) Uani 1 2 d S . .
C5 C 0.4446(3) 0.22230(15) 0.02785(12) 0.0451(11) Uani 1 2 d S . .
H5 H 0.4632 0.2316 0.0051 0.054 Uiso 1 2 calc SR . .
C6 C 0.3568(5) 0.1784(2) 0.13205(16) 0.0690(17) Uani 1 2 d S . .
C7 C 0.2930(7) 0.1897(6) 0.1434(2) 0.083(3) Uani 0.50 1 d P . 1
N1 N 0.2265(18) 0.186(2) 0.1102(14) 0.23(2) Uani 0.25 1 d P . 1
O4 O 0.185(3) 0.126(2) 0.0880(11) 0.28(3) Uani 0.25 1 d P . 1
O3 O 0.2140(16) 0.261(2) 0.1339(7) 0.231(14) Uani 0.25 1 d P . 1
C7' C 0.3969(8) 0.2439(6) 0.1556(2) 0.095(4) Uani 0.50 1 d P . 2

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 0.0508(3) 0.0508(3) 0.0292(3) -0.00133(10) 0.00133(10) 0.0406(3)
O1 0.0687(16) 0.0463(13) 0.0437(14) 0.0047(11) 0.0075(12) 0.0367(12)
O2 0.0790(17) 0.0546(15) 0.0460(14) 0.0104(12) 0.0146(13) 0.0466(14)
O7 0.123(3) 0.123(3) 0.088(4) -0.0376(16) 0.0376(16) 0.062(3)
C1 0.054(2) 0.0509(19) 0.042(2) 0.0009(15) -0.0019(16) 0.0364(17)
C2 0.057(2) 0.0500(19) 0.0414(19) 0.0013(15) -0.0010(16) 0.0361(17)
C3 0.073(2) 0.057(2) 0.046(2) 0.0070(17) 0.0127(18) 0.042(2)
C4 0.078(4) 0.050(2) 0.048(3) 0.0077(14) 0.015(3) 0.0390(19)
C5 0.058(3) 0.0471(19) 0.034(3) -0.0009(11) -0.002(2) 0.0291(15)
C6 0.114(5) 0.059(2) 0.053(4) 0.0126(17) 0.025(3) 0.057(3)
C7 0.135(9) 0.086(7) 0.058(6) 0.017(5) 0.034(6) 0.078(7)
N1 0.11(2) 0.19(3) 0.43(7) 0.19(4) 0.08(3) 0.11(2)
O4 0.25(4) 0.21(4) 0.33(4) -0.02(3) -0.01(3) 0.09(3)
O3 0.18(2) 0.37(4) 0.22(3) 0.08(3) -0.01(2) 0.20(3)
C7' 0.168(11) 0.070(6) 0.060(6) 0.006(5) 0.025(7) 0.069(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 1.951(2) 22_665 ?
Cu1 O1 1.951(2) . ?
Cu1 O2 1.968(2) 4 ?
Cu1 O2 1.968(2) 19_665 ?
Cu1 O7 2.143(4) . ?
Cu1 Cu1 2.6585(10) 19_665 ?
O1 C1 1.262(4) . ?
O2 C1 1.243(4) . ?
O2 Cu1 1.968(2) 19_665 ?
C1 C2 1.482(5) . ?
C2 C5 1.380(4) . ?
C2 C3 1.396(5) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C3 1.386(4) 23 ?
C4 C6 1.509(8) . ?
C5 C2 1.380(4) 23 ?
C5 H5 0.9300 . ?
C6 C7 1.374(11) 23 ?
C6 C7 1.374(11) . ?
C6 C7' 1.398(12) . ?
C6 C7' 1.398(12) 23 ?
C7 C7 1.603(19) 23 ?
C7 N1 1.76(4) . ?
N1 O4 1.30(6) . ?
N1 O3 1.78(5) . ?
O4 O4 1.25(7) 23 ?
C7' C7' 1.688(18) 23 ?

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 88.72(14) 22_665 . ?
O1 Cu1 O2 167.65(10) 22_665 4 ?
O1 Cu1 O2 89.90(11) . 4 ?
O1 Cu1 O2 89.90(11) 22_665 19_665 ?
O1 Cu1 O2 167.65(10) . 19_665 ?
O2 Cu1 O2 88.83(16) 4 19_665 ?
O1 Cu1 O7 98.18(13) 22_665 . ?
O1 Cu1 O7 98.18(13) . . ?
O2 Cu1 O7 94.17(14) 4 . ?
O2 Cu1 O7 94.17(14) 19_665 . ?
O1 Cu1 Cu1 83.79(7) 22_665 19_665 ?
O1 Cu1 Cu1 83.79(7) . 19_665 ?
O2 Cu1 Cu1 83.86(7) 4 19_665 ?
O2 Cu1 Cu1 83.86(7) 19_665 19_665 ?
O7 Cu1 Cu1 177.23(17) . 19_665 ?
C1 O1 Cu1 123.1(2) . . ?
C1 O2 Cu1 122.5(2) . 19_665 ?
O2 C1 O1 126.5(3) . . ?
O2 C1 C2 117.1(3) . . ?
O1 C1 C2 116.4(3) . . ?
C5 C2 C3 118.6(3) . . ?
C5 C2 C1 121.4(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C3 119.4(5) . 23 ?
C3 C4 C6 120.2(2) . . ?
C3 C4 C6 120.2(2) 23 . ?
C2 C5 C2 122.1(4) . 23 ?
C2 C5 H5 119.0 . . ?
C2 C5 H5 119.0 23 . ?
C7 C6 C7 71.4(9) 23 . ?
C7 C6 C7' 119.2(7) 23 . ?
C7 C6 C7' 77.5(7) . . ?
C7 C6 C7' 77.5(7) 23 23 ?
C7 C6 C7' 119.2(7) . 23 ?
C7' C6 C7' 74.3(9) . 23 ?
C7 C6 C4 122.1(6) 23 . ?
C7 C6 C4 122.1(6) . . ?
C7' C6 C4 118.7(6) . . ?
C7' C6 C4 118.7(6) 23 . ?
C6 C7 C7 54.3(4) . 23 ?
C6 C7 N1 113.7(17) . . ?
C7 C7 N1 108.1(15) 23 . ?
O4 N1 C7 128(3) . . ?
O4 N1 O3 139(3) . . ?
C7 N1 O3 87(3) . . ?
O4 O4 N1 124(2) 23 . ?
C6 C7' C7' 52.9(5) . 23 ?

# 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 -0.013 -0.014 -0.017 4793 2138 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1529128'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-30 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 H13 Cu2 F3 O10'
_chemical_formula_weight         633.41

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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, -x+y, -z'
'x-y, -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+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   18.5503(6)
_cell_length_b                   18.5503(6)
_cell_length_c                   38.8068(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11564.9(6)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    66045
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2844
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8325
_exptl_absorpt_correction_T_max  0.9033
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            66045
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_sigmaI/netI    0.0491
_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       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2506
_reflns_number_gt                1944
_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)+(0.0867P)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     SHELXL
_refine_ls_extinction_coef       0.00081(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2506
_refine_ls_number_parameters     116
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.220
_refine_ls_shift/su_max          0.001
_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
C1 C 0.4522(2) 0.0919(2) 0.02763(9) 0.0377(9) Uani 1 1 d . . .
C2 C 0.4300(2) 0.1505(2) 0.04467(9) 0.0366(9) Uani 1 1 d . A .
C3 C 0.4449(3) 0.22244(17) 0.02802(12) 0.0369(12) Uani 1 2 d S . .
H3 H 0.4650 0.2325 0.0055 0.044 Uiso 1 2 calc SR A .
C4 C 0.4000(3) 0.1347(2) 0.07805(10) 0.0458(10) Uani 1 1 d . . .
H4 H 0.3904 0.0863 0.0892 0.055 Uiso 1 1 calc R A .
C5 C 0.3841(4) 0.1921(2) 0.09499(15) 0.0509(16) Uani 1 2 d S . .
C6 C 0.3561(5) 0.1781(2) 0.13208(15) 0.0558(17) Uani 1 2 d SU . .
Cu1 Cu 0.524059(16) 0.04812(3) -0.027862(13) 0.0282(3) Uani 1 2 d S . .
O1 O 0.48133(16) 0.11018(15) -0.00268(6) 0.0409(7) Uani 1 1 d . A -1
O2 O 0.44081(19) 0.02942(15) 0.04454(6) 0.0454(7) Uani 1 1 d . . -1
O1W O 0.56226(19) 0.1245(4) -0.07305(14) 0.108(2) Uani 1 2 d S A .
C7 C 0.2818(3) 0.1040(3) 0.14234(12) 0.065(3) Uani 0.50 1 d PDU . .
H7A H 0.2466 0.0626 0.1254 0.078 Uiso 0.25 1 d PR B 1
C9 C 0.2153(3) 0.0346(3) 0.11670(12) 0.097(9) Uani 0.25 1 d PRD . 2
F1 F 0.2050(3) 0.0673(3) 0.08738(12) 0.099(5) Uani 0.25 1 d PRD . 2
F2 F 0.2392(3) -0.0211(3) 0.11017(12) 0.116(5) Uani 0.25 1 d PRD . 2
F3 F 0.1392(3) -0.0104(3) 0.13060(12) 0.157(8) Uani 0.25 1 d PRD . 2
C8 C 0.2659(3) 0.0961(3) 0.17691(12) 0.061(2) Uani 0.50 1 d PRU . .
H8A H 0.2145 0.0564 0.1877 0.073 Uiso 0.50 1 d PR . .

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
C1 0.051(2) 0.028(2) 0.031(2) -0.0078(16) -0.0052(17) 0.0172(18)
C2 0.051(2) 0.0296(19) 0.0277(19) -0.0041(15) -0.0022(17) 0.0192(18)
C3 0.050(3) 0.039(2) 0.025(3) -0.0018(12) -0.004(2) 0.0252(17)
C4 0.069(3) 0.036(2) 0.036(2) 0.0020(17) 0.007(2) 0.029(2)
C5 0.082(5) 0.050(2) 0.032(3) 0.0055(15) 0.011(3) 0.041(2)
C6 0.095(5) 0.047(2) 0.041(3) 0.0063(16) 0.013(3) 0.047(2)
Cu1 0.0423(4) 0.0175(4) 0.0166(4) 0.0007(2) 0.00033(11) 0.00876(18)
O1 0.0607(18) 0.0362(15) 0.0293(14) 0.0030(11) 0.0062(12) 0.0268(14)
O2 0.077(2) 0.0337(15) 0.0303(14) 0.0016(12) 0.0093(13) 0.0314(14)
O1W 0.122(3) 0.126(5) 0.078(4) 0.083(4) 0.0417(18) 0.063(2)
C7 0.098(7) 0.052(5) 0.046(5) 0.007(4) 0.015(4) 0.038(5)
C9 0.058(13) 0.082(16) 0.059(13) -0.035(12) 0.032(11) -0.035(12)
F1 0.103(9) 0.118(11) 0.034(5) 0.000(5) 0.000(6) 0.025(8)
F2 0.113(11) 0.068(8) 0.114(11) -0.061(8) 0.015(9) 0.005(8)
F3 0.119(12) 0.150(13) 0.066(8) -0.068(8) 0.024(8) -0.033(10)
C8 0.092(6) 0.053(5) 0.043(5) 0.004(4) 0.015(4) 0.040(5)

_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
C1 O2 1.254(4) . ?
C1 O1 1.268(4) . ?
C1 C2 1.496(5) . ?
C2 C3 1.380(4) . ?
C2 C4 1.382(5) . ?
C3 C2 1.380(4) 23 ?
C3 H3 0.9300 . ?
C4 C5 1.401(5) . ?
C4 H4 0.9300 . ?
C5 C4 1.401(5) 23 ?
C5 C6 1.508(8) . ?
C6 C8 1.369(7) 11 ?
C6 C8 1.370(7) 25 ?
C6 C7 1.433(7) . ?
C6 C7 1.433(7) 23 ?
Cu1 O1 1.955(2) 24_655 ?
Cu1 O1 1.955(2) . ?
Cu1 O2 1.962(2) 6 ?
Cu1 O2 1.962(2) 19_655 ?
Cu1 O1W 2.141(4) . ?
Cu1 Cu1 2.6583(10) 19_655 ?
O2 Cu1 1.962(2) 19_655 ?
C7 C8 1.3658 . ?
C7 C7 1.369(10) 23 ?
C7 C9 1.6067 . ?
C7 C8 1.933(7) 23 ?
C7 C8 1.988(10) 11 ?
C7 H7A 0.9730 . ?
C9 F2 1.3364 . ?
C9 F3 1.3419 . ?
C9 F1 1.3468 . ?
C9 H7A 0.6476 . ?
F1 F1 1.306(10) 23 ?
C8 C6 1.370(7) 25 ?
C8 C8 1.368(10) 23 ?
C8 C7 1.933(7) 23 ?
C8 C7 1.988(10) 11 ?
C8 H8A 0.9600 . ?

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
O2 C1 O1 125.8(3) . . ?
O2 C1 C2 117.4(3) . . ?
O1 C1 C2 116.8(3) . . ?
C3 C2 C4 120.6(4) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C2 C1 119.2(3) . . ?
C2 C3 C2 120.1(5) . 23 ?
C2 C3 H3 120.0 . . ?
C2 C3 H3 120.0 23 . ?
C2 C4 C5 119.6(4) . . ?
C2 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C4 119.6(5) 23 . ?
C4 C5 C6 120.1(3) 23 . ?
C4 C5 C6 120.1(3) . . ?
C8 C6 C8 59.9(5) 11 25 ?
C8 C6 C7 90.4(5) 11 . ?
C8 C6 C7 118.9(5) 25 . ?
C8 C6 C7 118.9(5) 11 23 ?
C8 C6 C7 90.4(5) 25 23 ?
C7 C6 C7 57.1(5) . 23 ?
C8 C6 C5 120.2(5) 11 . ?
C8 C6 C5 120.2(5) 25 . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 C5 120.9(5) 23 . ?
O1 Cu1 O1 88.84(15) 24_655 . ?
O1 Cu1 O2 167.89(10) 24_655 6 ?
O1 Cu1 O2 89.98(12) . 6 ?
O1 Cu1 O2 89.98(12) 24_655 19_655 ?
O1 Cu1 O2 167.89(10) . 19_655 ?
O2 Cu1 O2 88.64(17) 6 19_655 ?
O1 Cu1 O1W 96.73(15) 24_655 . ?
O1 Cu1 O1W 96.73(15) . . ?
O2 Cu1 O1W 95.38(15) 6 . ?
O2 Cu1 O1W 95.38(15) 19_655 . ?
O1 Cu1 Cu1 83.68(7) 24_655 19_655 ?
O1 Cu1 Cu1 83.68(7) . 19_655 ?
O2 Cu1 Cu1 84.21(7) 6 19_655 ?
O2 Cu1 Cu1 84.21(7) 19_655 19_655 ?
O1W Cu1 Cu1 179.4(2) . 19_655 ?
C1 O1 Cu1 123.4(2) . . ?
C1 O2 Cu1 122.7(2) . 19_655 ?
C8 C7 C7 90.0 . 23 ?
C8 C7 C6 115.4(3) . . ?
C7 C7 C6 61.5(2) 23 . ?
C8 C7 C9 118.9 . . ?
C7 C7 C9 114.640(2) 23 . ?
C6 C7 C9 125.6(3) . . ?
C8 C7 C8 45.0(2) . 23 ?
C7 C7 C8 44.9(2) 23 23 ?
C6 C7 C8 88.0(3) . 23 ?
C9 C7 C8 129.5 . 23 ?
C8 C7 C8 84.8(3) . 11 ?
C7 C7 C8 89.977(1) 23 11 ?
C6 C7 C8 43.5(3) . 11 ?
C9 C7 C8 144.11(18) . 11 ?
C8 C7 C8 86.35(18) 23 11 ?
C8 C7 H7A 123.7 . . ?
C7 C7 H7A 116.9 23 . ?
C6 C7 H7A 120.9 . . ?
C9 C7 H7A 6.1 . . ?
C8 C7 H7A 135.4 23 . ?
C8 C7 H7A 138.2 11 . ?
F2 C9 F3 104.3 . . ?
F2 C9 F1 111.3 . . ?
F3 C9 F1 106.2 . . ?
F2 C9 C7 108.5 . . ?
F3 C9 C7 113.4 . . ?
F1 C9 C7 112.8 . . ?
F2 C9 H7A 102.0 . . ?
F3 C9 H7A 122.1 . . ?
F1 C9 H7A 110.6 . . ?
C7 C9 H7A 9.2 . . ?
F1 F1 C9 121.4 23 . ?
C7 C8 C6 125.4(3) . 25 ?
C7 C8 C8 90.0 . 23 ?
C6 C8 C8 60.0(3) 25 23 ?
C7 C8 C7 45.1(2) . 23 ?
C6 C8 C7 93.2(4) 25 23 ?
C8 C8 C7 44.9(2) 23 23 ?
C7 C8 C7 95.2(3) . 11 ?
C6 C8 C7 46.1(3) 25 11 ?
C8 C8 C7 90.0 23 11 ?
C7 C8 C7 93.65(18) 23 11 ?
C7 C8 H8A 126.0 . . ?
C6 C8 H8A 106.5 25 . ?
C8 C8 H8A 105.6 23 . ?
C7 C8 H8A 127.3 23 . ?
C7 C8 H8A 134.9 11 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 176.8(4) . . . . ?
O1 C1 C2 C3 -2.8(6) . . . . ?
O2 C1 C2 C4 1.3(6) . . . . ?
O1 C1 C2 C4 -178.3(3) . . . . ?
C4 C2 C3 C2 0.1(8) . . . 23 ?
C1 C2 C3 C2 -175.4(3) . . . 23 ?
C3 C2 C4 C5 0.4(7) . . . . ?
C1 C2 C4 C5 175.9(4) . . . . ?
C2 C4 C5 C4 -0.9(9) . . . 23 ?
C2 C4 C5 C6 -176.4(5) . . . . ?
C4 C5 C6 C8 -123.0(5) 23 . . 11 ?
C4 C5 C6 C8 52.5(8) . . . 11 ?
C4 C5 C6 C8 -52.5(8) 23 . . 25 ?
C4 C5 C6 C8 123.0(5) . . . 25 ?
C4 C5 C6 C7 126.1(5) 23 . . . ?
C4 C5 C6 C7 -58.4(8) . . . . ?
C4 C5 C6 C7 58.4(8) 23 . . 23 ?
C4 C5 C6 C7 -126.1(5) . . . 23 ?
O2 C1 O1 Cu1 -5.6(6) . . . . ?
C2 C1 O1 Cu1 174.0(2) . . . . ?
O1 Cu1 O1 C1 -81.1(3) 24_655 . . . ?
O2 Cu1 O1 C1 86.9(3) 6 . . . ?
O2 Cu1 O1 C1 3.4(7) 19_655 . . . ?
O1W Cu1 O1 C1 -177.7(3) . . . . ?
Cu1 Cu1 O1 C1 2.7(3) 19_655 . . . ?
O1 C1 O2 Cu1 5.4(6) . . . 19_655 ?
C2 C1 O2 Cu1 -174.2(2) . . . 19_655 ?
C8 C6 C7 C8 49.9(3) 11 . . . ?
C8 C6 C7 C8 -5.4(4) 25 . . . ?
C7 C6 C7 C8 -75.0(3) 23 . . . ?
C5 C6 C7 C8 176.0(3) . . . . ?
C8 C6 C7 C7 124.9(3) 11 . . 23 ?
C8 C6 C7 C7 69.6(3) 25 . . 23 ?
C5 C6 C7 C7 -109.0(5) . . . 23 ?
C8 C6 C7 C9 -133.9(2) 11 . . . ?
C8 C6 C7 C9 170.8(3) 25 . . . ?
C7 C6 C7 C9 101.2(2) 23 . . . ?
C5 C6 C7 C9 -7.8(5) . . . . ?
C8 C6 C7 C8 86.8(4) 11 . . 23 ?
C8 C6 C7 C8 31.5(3) 25 . . 23 ?
C7 C6 C7 C8 -38.1(2) 23 . . 23 ?
C5 C6 C7 C8 -147.1(3) . . . 23 ?
C8 C6 C7 C8 -55.3(5) 25 . . 11 ?
C7 C6 C7 C8 -124.9(3) 23 . . 11 ?
C5 C6 C7 C8 126.1(5) . . . 11 ?
C8 C7 C9 F2 -96.0 . . . . ?
C7 C7 C9 F2 159.335(2) 23 . . . ?
C6 C7 C9 F2 87.9(3) . . . . ?
C8 C7 C9 F2 -149.8(3) 23 . . . ?
C8 C7 C9 F2 30.1(3) 11 . . . ?
C8 C7 C9 F3 19.4 . . . . ?
C7 C7 C9 F3 -85.288(1) 23 . . . ?
C6 C7 C9 F3 -156.7(3) . . . . ?
C8 C7 C9 F3 -34.4(3) 23 . . . ?
C8 C7 C9 F3 145.4(3) 11 . . . ?
C8 C7 C9 F1 140.1 . . . . ?
C7 C7 C9 F1 35.466(2) 23 . . . ?
C6 C7 C9 F1 -36.0(3) . . . . ?
C8 C7 C9 F1 86.3(3) 23 . . . ?
C8 C7 C9 F1 -93.8(3) 11 . . . ?
F2 C9 F1 F1 -160.4 . . . 23 ?
F3 C9 F1 F1 86.6 . . . 23 ?
C7 C9 F1 F1 -38.2 . . . 23 ?
C7 C7 C8 C6 -52.2(4) 23 . . 25 ?
C6 C7 C8 C6 5.8(4) . . . 25 ?
C9 C7 C8 C6 -170.7(4) . . . 25 ?
C8 C7 C8 C6 -52.2(4) 23 . . 25 ?
C8 C7 C8 C6 37.7(4) 11 . . 25 ?
C7 C7 C8 C8 0.000(1) 23 . . 23 ?
C6 C7 C8 C8 58.1(3) . . . 23 ?
C9 C7 C8 C8 -118.4 . . . 23 ?
C8 C7 C8 C8 90.0 11 . . 23 ?
C6 C7 C8 C7 58.1(3) . . . 23 ?
C9 C7 C8 C7 -118.4 . . . 23 ?
C8 C7 C8 C7 0.000(1) 23 . . 23 ?
C8 C7 C8 C7 89.979(2) 11 . . 23 ?
C7 C7 C8 C7 -90.022(1) 23 . . 11 ?
C6 C7 C8 C7 -32.0(3) . . . 11 ?
C9 C7 C8 C7 151.5 . . . 11 ?
C8 C7 C8 C7 -90.0 23 . . 11 ?
C8 C7 C8 C7 0.0 11 . . 11 ?

# 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 -0.083 -0.067 -0.003 6312 2650 ' '
_platon_squeeze_details          
;
;
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.180
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1529131'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 Cu2 F O10'
_chemical_formula_weight         583.40

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'
Cu Cu 0.3201 1.2651 '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'
F F 0.0171 0.0103 '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, -x+y, -z'
'x-y, -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+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   18.7065(19)
_cell_length_b                   18.7065(19)
_cell_length_c                   38.488(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11663.8(19)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    66423
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2628
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8095
_exptl_absorpt_correction_T_max  0.9050
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            66423
_diffrn_reflns_av_R_equivalents  0.2139
_diffrn_reflns_av_sigmaI/netI    0.0779
_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       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2523
_reflns_number_gt                1772
_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)+(0.0692P)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         2523
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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
C1 C 0.4531(3) 0.3601(3) 0.02636(11) 0.0322(10) Uani 1 1 d . . .
C2 C 0.4318(3) 0.2803(3) 0.04362(10) 0.0326(10) Uani 1 1 d . C .
C3 C 0.4468(4) 0.22338(19) 0.02691(14) 0.0321(14) Uani 1 2 d S . .
H3 H 0.4670 0.2335 0.0043 0.039 Uiso 1 2 calc SR C .
C4 C 0.4016(3) 0.2645(3) 0.07734(11) 0.0402(12) Uani 1 1 d . . .
H4 H 0.3904 0.3019 0.0885 0.048 Uiso 1 1 calc R C .
C5 C 0.3878(4) 0.1939(2) 0.09475(16) 0.0418(17) Uani 1 2 d S . .
C6 C 0.3587(5) 0.1794(2) 0.13153(16) 0.0444(19) Uani 1 2 d S . .
C8 C 0.2734(7) 0.1843(6) 0.1779(2) 0.051(3) Uani 0.50 1 d P . .
H8A H 0.2312 0.1959 0.1852 0.062 Uiso 0.50 1 d PR C .
C7 C 0.3003(7) 0.1970(6) 0.1434(2) 0.049(3) Uani 0.50 1 d P . .
H7A H 0.2771 0.2200 0.1278 0.058 Uiso 0.25 1 d PR A 1
F1 F 0.2525(10) 0.2211(10) 0.1208(4) 0.098(5) Uani 0.25 1 d P B 2
Cu1 Cu 0.52331(2) 0.47669(2) -0.028389(16) 0.0242(3) Uani 1 2 d S . .
O1 O 0.48255(19) 0.37154(17) -0.00394(7) 0.0379(8) Uani 1 1 d . C -1
O2 O 0.4418(2) 0.41065(18) 0.04372(7) 0.0398(8) Uani 1 1 d . . -1
O1W O 0.55672(18) 0.44328(18) -0.07702(13) 0.0820(18) Uani 1 2 d S C .

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
C1 0.032(3) 0.037(3) 0.033(3) 0.003(2) -0.004(2) 0.022(2)
C2 0.041(3) 0.030(2) 0.032(2) -0.0008(19) 0.003(2) 0.021(2)
C3 0.039(4) 0.035(3) 0.024(3) 0.0013(14) 0.003(3) 0.0194(19)
C4 0.060(3) 0.033(3) 0.036(3) 0.002(2) 0.006(2) 0.030(3)
C5 0.064(5) 0.033(3) 0.039(4) 0.0067(17) 0.013(3) 0.032(2)
C6 0.070(5) 0.036(3) 0.038(4) 0.0105(17) 0.021(3) 0.035(3)
C8 0.086(8) 0.051(6) 0.041(6) 0.017(5) 0.028(6) 0.052(7)
C7 0.074(8) 0.051(7) 0.038(5) 0.017(5) 0.014(5) 0.043(6)
F1 0.118(13) 0.122(13) 0.082(9) 0.041(9) 0.029(9) 0.082(12)
Cu1 0.0311(4) 0.0311(4) 0.0193(4) -0.00010(15) 0.00010(15) 0.0222(4)
O1 0.059(2) 0.0314(18) 0.0319(16) 0.0050(13) 0.0097(15) 0.0289(16)
O2 0.067(2) 0.0358(18) 0.0331(16) 0.0061(14) 0.0107(15) 0.0379(18)
O1W 0.085(3) 0.085(3) 0.069(4) -0.0272(16) 0.0272(16) 0.038(4)

_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
C1 O2 1.260(5) . ?
C1 O1 1.261(5) . ?
C1 C2 1.494(6) . ?
C2 C3 1.387(5) . ?
C2 C4 1.387(5) . ?
C3 C2 1.387(5) 23 ?
C3 H3 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9300 . ?
C5 C4 1.385(5) 23 ?
C5 C6 1.492(8) . ?
C6 C7 1.368(11) 23 ?
C6 C7 1.368(11) . ?
C6 C8 1.397(11) 25 ?
C6 C8 1.397(11) 11 ?
C8 C6 1.397(11) 25 ?
C8 C7 1.398(12) . ?
C8 C7 1.575(15) 11 ?
C8 C8 1.780(17) 23 ?
C8 H8A 0.9599 . ?
C7 F1 1.472(16) . ?
C7 C8 1.575(15) 11 ?
C7 C7 1.752(19) 23 ?
C7 H7A 0.9600 . ?
F1 H7A 0.5430 . ?
Cu1 O1 1.959(3) 22_665 ?
Cu1 O1 1.959(3) . ?
Cu1 O2 1.960(3) 4 ?
Cu1 O2 1.960(3) 19_665 ?
Cu1 O1W 2.162(5) . ?
Cu1 Cu1 2.6564(12) 19_665 ?
O2 Cu1 1.960(3) 19_665 ?

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
O2 C1 O1 125.8(4) . . ?
O2 C1 C2 117.0(4) . . ?
O1 C1 C2 117.2(4) . . ?
C3 C2 C4 119.2(4) . . ?
C3 C2 C1 120.3(4) . . ?
C4 C2 C1 120.4(4) . . ?
C2 C3 C2 120.6(5) . 23 ?
C2 C3 H3 119.7 . . ?
C2 C3 H3 119.7 23 . ?
C5 C4 C2 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C2 C4 H4 119.4 . . ?
C4 C5 C4 118.7(6) . 23 ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C6 120.7(3) 23 . ?
C7 C6 C7 79.6(9) 23 . ?
C7 C6 C8 69.5(6) 23 25 ?
C7 C6 C8 117.7(7) . 25 ?
C7 C6 C8 117.7(7) 23 11 ?
C7 C6 C8 69.5(6) . 11 ?
C8 C6 C8 79.2(9) 25 11 ?
C7 C6 C5 122.3(6) 23 . ?
C7 C6 C5 122.3(6) . . ?
C8 C6 C5 119.9(6) 25 . ?
C8 C6 C5 119.9(6) 11 . ?
C6 C8 C7 119.7(9) 25 . ?
C6 C8 C7 54.4(6) 25 11 ?
C7 C8 C7 89.0(8) . 11 ?
C6 C8 C8 50.4(4) 25 23 ?
C7 C8 C8 89.4(6) . 23 ?
C7 C8 C8 89.5(5) 11 23 ?
C6 C8 H8A 120.0 25 . ?
C7 C8 H8A 120.3 . . ?
C7 C8 H8A 127.0 11 . ?
C8 C8 H8A 129.6 23 . ?
C6 C7 C8 122.6(9) . . ?
C6 C7 F1 123.9(9) . . ?
C8 C7 F1 113.1(10) . . ?
C6 C7 C8 56.1(6) . 11 ?
C8 C7 C8 91.0(8) . 11 ?
F1 C7 C8 132.2(10) . 11 ?
C6 C7 C7 50.2(4) . 23 ?
C8 C7 C7 90.6(6) . 23 ?
F1 C7 C7 127.6(8) . 23 ?
C8 C7 C7 90.5(5) 11 23 ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 117.8 . . ?
F1 C7 H7A 8.8 . . ?
C8 C7 H7A 123.5 11 . ?
C7 C7 H7A 132.4 23 . ?
C7 F1 H7A 15.6 . . ?
O1 Cu1 O1 88.34(18) 22_665 . ?
O1 Cu1 O2 167.91(11) 22_665 4 ?
O1 Cu1 O2 89.79(13) . 4 ?
O1 Cu1 O2 89.79(13) 22_665 19_665 ?
O1 Cu1 O2 167.91(11) . 19_665 ?
O2 Cu1 O2 89.54(19) 4 19_665 ?
O1 Cu1 O1W 98.58(14) 22_665 . ?
O1 Cu1 O1W 98.58(14) . . ?
O2 Cu1 O1W 93.51(14) 4 . ?
O2 Cu1 O1W 93.51(14) 19_665 . ?
O1 Cu1 Cu1 84.70(8) 22_665 19_665 ?
O1 Cu1 Cu1 84.70(8) . 19_665 ?
O2 Cu1 Cu1 83.23(8) 4 19_665 ?
O2 Cu1 Cu1 83.23(8) 19_665 19_665 ?
O1W Cu1 Cu1 175.40(18) . 19_665 ?
C1 O1 Cu1 122.2(3) . . ?
C1 O2 Cu1 123.9(3) . 19_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -176.4(4) . . . . ?
O1 C1 C2 C3 1.9(6) . . . . ?
O2 C1 C2 C4 -0.4(6) . . . . ?
O1 C1 C2 C4 178.0(4) . . . . ?
C4 C2 C3 C2 -0.1(9) . . . 23 ?
C1 C2 C3 C2 176.1(3) . . . 23 ?
C3 C2 C4 C5 1.4(8) . . . . ?
C1 C2 C4 C5 -174.8(5) . . . . ?
C2 C4 C5 C4 -2.6(10) . . . 23 ?
C2 C4 C5 C6 177.3(5) . . . . ?
C4 C5 C6 C7 139.3(7) . . . 23 ?
C4 C5 C6 C7 -40.8(10) 23 . . 23 ?
C4 C5 C6 C7 40.8(10) . . . . ?
C4 C5 C6 C7 -139.3(7) 23 . . . ?
C4 C5 C6 C8 -137.3(7) . . . 25 ?
C4 C5 C6 C8 42.6(10) 23 . . 25 ?
C4 C5 C6 C8 -42.6(10) . . . 11 ?
C4 C5 C6 C8 137.3(7) 23 . . 11 ?
C7 C6 C7 C8 58.9(13) 23 . . . ?
C8 C6 C7 C8 -1.2(16) 25 . . . ?
C8 C6 C7 C8 -66.2(10) 11 . . . ?
C5 C6 C7 C8 -179.3(9) . . . . ?
C7 C6 C7 F1 -113.4(11) 23 . . . ?
C8 C6 C7 F1 -173.5(12) 25 . . . ?
C8 C6 C7 F1 121.6(14) 11 . . . ?
C5 C6 C7 F1 8.4(15) . . . . ?
C7 C6 C7 C8 125.0(6) 23 . . 11 ?
C8 C6 C7 C8 65.0(9) 25 . . 11 ?
C5 C6 C7 C8 -113.2(7) . . . 11 ?
C8 C6 C7 C7 -60.1(6) 25 . . 23 ?
C8 C6 C7 C7 -125.0(6) 11 . . 23 ?
C5 C6 C7 C7 121.8(9) . . . 23 ?
C6 C8 C7 C6 1.2(17) 25 . . . ?
C7 C8 C7 C6 48.4(13) 11 . . . ?
C8 C8 C7 C6 -41.1(9) 23 . . . ?
C6 C8 C7 F1 174.3(11) 25 . . . ?
C7 C8 C7 F1 -138.6(10) 11 . . . ?
C8 C8 C7 F1 131.9(11) 23 . . . ?
C6 C8 C7 C8 -48.2(12) 25 . . 11 ?
C7 C8 C7 C8 -1.0(10) 11 . . 11 ?
C8 C8 C7 C8 -90.5(5) 23 . . 11 ?
C6 C8 C7 C7 42.3(9) 25 . . 23 ?
C7 C8 C7 C7 89.5(5) 11 . . 23 ?
C8 C8 C7 C7 0.000(1) 23 . . 23 ?
O2 C1 O1 Cu1 4.1(6) . . . . ?
C2 C1 O1 Cu1 -174.1(3) . . . . ?
O1 Cu1 O1 C1 83.6(3) 22_665 . . . ?
O2 Cu1 O1 C1 -84.4(3) 4 . . . ?
O2 Cu1 O1 C1 2.4(8) 19_665 . . . ?
O1W Cu1 O1 C1 -178.0(3) . . . . ?
Cu1 Cu1 O1 C1 -1.2(3) 19_665 . . . ?
O1 C1 O2 Cu1 -5.2(6) . . . 19_665 ?
C2 C1 O2 Cu1 172.9(3) . . . 19_665 ?

# 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 -0.073 -0.054 -0.003 7479 3069 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.139
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1529132'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-30 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 O10'
_chemical_formula_weight         579.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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'

_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, -x+y, -z'
'x-y, -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+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, -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+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'x, x-y, z'
'-x+y, 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+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, 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+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'

_cell_length_a                   18.6166(7)
_cell_length_b                   18.6166(7)
_cell_length_c                   38.6451(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11599.1(7)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    65985
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2628
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8483
_exptl_absorpt_correction_T_max  0.8759
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            65985
_diffrn_reflns_av_R_equivalents  0.1541
_diffrn_reflns_av_sigmaI/netI    0.0646
_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       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2512
_reflns_number_gt                1806
_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)+(0.1117P)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     SHELXL
_refine_ls_extinction_coef       0.00058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     92
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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
C1 C 0.4515(3) 0.0919(3) 0.02706(11) 0.0353(11) Uani 1 1 d . . .
C2 C 0.4310(3) 0.1511(3) 0.04412(11) 0.0363(11) Uani 1 1 d . A .
C3 C 0.4451(4) 0.2226(2) 0.02798(16) 0.0369(16) Uani 1 2 d S . .
H3 H 0.4649 0.2324 0.0054 0.044 Uiso 1 2 calc SR A .
C4 C 0.3999(3) 0.1364(3) 0.07751(12) 0.0433(13) Uani 1 1 d . . .
H4 H 0.3889 0.0875 0.0885 0.052 Uiso 1 1 calc R A .
C5 C 0.3849(5) 0.1925(2) 0.09492(18) 0.0442(18) Uani 1 2 d S . .
C6 C 0.3567(5) 0.1783(3) 0.13203(19) 0.051(2) Uani 1 2 d SU . .
Cu1 Cu 0.52365(2) 0.04730(4) -0.028037(17) 0.0269(3) Uani 1 2 d S . .
O1 O 0.4814(2) 0.11035(18) -0.00323(8) 0.0416(9) Uani 1 1 d . A -1
O2 O 0.4412(2) 0.02993(19) 0.04420(8) 0.0439(9) Uani 1 1 d . . -1
O1W O 0.5592(2) 0.1183(4) -0.07537(16) 0.092(2) Uani 1 2 d S A .
C7 C 0.2899(5) 0.1017(5) 0.1427(2) 0.067(3) Uani 0.50 1 d PU . .
H7A H 0.2547 0.0603 0.1257 0.081 Uiso 0.25 1 d PR B 1
C9 C 0.2234(5) 0.0323(5) 0.1170(2) 0.067(3) Uani 0.25 1 d PR B 2
H9A H 0.1833 -0.0141 0.1303 0.101 Uiso 0.25 1 calc PR B 2
H9B H 0.2513 0.0142 0.1015 0.101 Uiso 0.25 1 calc PR B 2
H9C H 0.1958 0.0554 0.1040 0.101 Uiso 0.25 1 calc PR B 2
C8 C 0.2740(5) 0.0938(5) 0.1772(2) 0.059(3) Uani 0.50 1 d PRU . .
H8A H 0.2227 0.0542 0.1880 0.071 Uiso 0.50 1 d PR . .

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
C1 0.039(3) 0.029(3) 0.031(3) -0.006(2) -0.001(2) 0.012(2)
C2 0.048(3) 0.031(3) 0.029(2) 0.002(2) 0.005(2) 0.020(2)
C3 0.051(4) 0.042(3) 0.021(3) 0.0025(15) 0.005(3) 0.025(2)
C4 0.060(3) 0.036(3) 0.041(3) 0.007(2) 0.010(2) 0.029(3)
C5 0.063(5) 0.037(3) 0.041(4) 0.0051(18) 0.010(4) 0.032(2)
C6 0.079(5) 0.044(3) 0.042(4) 0.0102(19) 0.020(4) 0.040(3)
Cu1 0.0380(4) 0.0174(4) 0.0184(4) 0.0004(3) 0.00019(15) 0.0087(2)
O1 0.065(2) 0.0358(19) 0.0333(18) 0.0014(15) 0.0080(17) 0.0319(18)
O2 0.071(2) 0.0342(19) 0.0357(19) 0.0052(15) 0.0149(17) 0.0331(18)
O1W 0.103(4) 0.108(5) 0.067(4) 0.064(4) 0.0319(19) 0.054(3)
C7 0.082(7) 0.064(6) 0.049(5) -0.001(4) 0.012(5) 0.031(5)
C9 0.082(7) 0.064(6) 0.049(5) -0.001(4) 0.012(5) 0.031(5)
C8 0.088(7) 0.047(6) 0.050(6) 0.006(5) 0.019(5) 0.039(5)

_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
C1 O2 1.259(5) . ?
C1 O1 1.268(5) . ?
C1 C2 1.489(6) . ?
C2 C3 1.370(5) . ?
C2 C4 1.384(6) . ?
C3 C2 1.370(5) 23 ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C4 1.383(6) 23 ?
C5 C6 1.505(10) . ?
C6 C8 1.360(10) 11 ?
C6 C8 1.360(10) 25 ?
C6 C7 1.405(9) 23 ?
C6 C7 1.405(9) . ?
Cu1 O2 1.956(3) 6 ?
Cu1 O2 1.956(3) 19_655 ?
Cu1 O1 1.959(3) . ?
Cu1 O1 1.959(3) 24_655 ?
Cu1 O1W 2.158(5) . ?
Cu1 Cu1 2.6499(13) 19_655 ?
O2 Cu1 1.956(3) 19_655 ?
C7 C8 1.3605 . ?
C7 C9 1.6077 . ?
C7 C7 1.610(14) 23 ?
C7 C8 1.735(16) 11 ?
C7 H7A 0.9731 . ?
C9 H7A 0.6486 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 C6 1.360(10) 25 ?
C8 C8 1.609(14) 23 ?
C8 C7 1.735(16) 11 ?
C8 H8A 0.9621 . ?

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
O2 C1 O1 125.4(4) . . ?
O2 C1 C2 117.8(4) . . ?
O1 C1 C2 116.7(4) . . ?
C3 C2 C4 118.4(4) . . ?
C3 C2 C1 121.4(4) . . ?
C4 C2 C1 120.2(4) . . ?
C2 C3 C2 122.0(6) 23 . ?
C2 C3 H3 119.0 23 . ?
C2 C3 H3 119.0 . . ?
C2 C4 C5 121.7(5) . . ?
C2 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C4 117.7(6) . 23 ?
C4 C5 C6 121.1(3) . . ?
C4 C5 C6 121.1(3) 23 . ?
C8 C6 C8 72.6(8) 11 25 ?
C8 C6 C7 117.8(7) 11 23 ?
C8 C6 C7 77.7(7) 25 23 ?
C8 C6 C7 77.7(7) 11 . ?
C8 C6 C7 117.8(7) 25 . ?
C7 C6 C7 69.9(6) 23 . ?
C8 C6 C5 121.5(6) 11 . ?
C8 C6 C5 121.5(6) 25 . ?
C7 C6 C5 120.7(6) 23 . ?
C7 C6 C5 120.7(6) . . ?
O2 Cu1 O2 89.2(2) 6 19_655 ?
O2 Cu1 O1 89.68(15) 6 . ?
O2 Cu1 O1 168.13(13) 19_655 . ?
O2 Cu1 O1 168.13(13) 6 24_655 ?
O2 Cu1 O1 89.68(15) 19_655 24_655 ?
O1 Cu1 O1 89.0(2) . 24_655 ?
O2 Cu1 O1W 93.85(17) 6 . ?
O2 Cu1 O1W 93.85(17) 19_655 . ?
O1 Cu1 O1W 98.01(16) . . ?
O1 Cu1 O1W 98.01(16) 24_655 . ?
O2 Cu1 Cu1 83.96(9) 6 19_655 ?
O2 Cu1 Cu1 83.96(9) 19_655 19_655 ?
O1 Cu1 Cu1 84.17(9) . 19_655 ?
O1 Cu1 Cu1 84.17(9) 24_655 19_655 ?
O1W Cu1 Cu1 176.9(2) . 19_655 ?
C1 O1 Cu1 122.9(3) . . ?
C1 O2 Cu1 123.5(3) . 19_655 ?
C8 C7 C6 115.6(5) . . ?
C8 C7 C9 118.6 . . ?
C6 C7 C9 124.7(5) . . ?
C8 C7 C7 89.969(1) . 23 ?
C6 C7 C7 55.0(3) . 23 ?
C9 C7 C7 114.718(1) . 23 ?
C8 C7 C8 83.5(5) . 11 ?
C6 C7 C8 50.0(4) . 11 ?
C9 C7 C8 145.2(3) . 11 ?
C7 C7 C8 89.973(2) 23 11 ?
C8 C7 H7A 123.4 . . ?
C6 C7 H7A 120.7 . . ?
C9 C7 H7A 6.1 . . ?
C7 C7 H7A 117.0 23 . ?
C8 C7 H7A 139.3 11 . ?
C7 C9 H7A 9.2 . . ?
C7 C9 H9A 109.5 . . ?
H7A C9 H9A 115.3 . . ?
C7 C9 H9B 109.5 . . ?
H7A C9 H9B 100.4 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H7A C9 H9C 112.2 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C8 C7 126.2(4) 25 . ?
C6 C8 C8 53.7(4) 25 23 ?
C7 C8 C8 90.0 . 23 ?
C6 C8 C7 52.3(5) 25 11 ?
C7 C8 C7 96.5(5) . 11 ?
C8 C8 C7 90.0 23 11 ?
C6 C8 H8A 103.4 25 . ?
C7 C8 H8A 125.9 . . ?
C8 C8 H8A 105.7 23 . ?
C7 C8 H8A 133.8 11 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 176.1(5) . . . . ?
O1 C1 C2 C3 -1.0(7) . . . . ?
O2 C1 C2 C4 -1.3(7) . . . . ?
O1 C1 C2 C4 -178.5(4) . . . . ?
C4 C2 C3 C2 1.3(10) . . . 23 ?
C1 C2 C3 C2 -176.2(4) . . . 23 ?
C3 C2 C4 C5 -1.5(9) . . . . ?
C1 C2 C4 C5 176.0(5) . . . . ?
C2 C4 C5 C4 1.6(11) . . . 23 ?
C2 C4 C5 C6 -175.8(6) . . . . ?
C4 C5 C6 C8 44.8(11) . . . 11 ?
C4 C5 C6 C8 -132.6(7) 23 . . 11 ?
C4 C5 C6 C8 132.6(7) . . . 25 ?
C4 C5 C6 C8 -44.7(11) 23 . . 25 ?
C4 C5 C6 C7 -133.1(6) . . . 23 ?
C4 C5 C6 C7 49.5(10) 23 . . 23 ?
C4 C5 C6 C7 -49.5(10) . . . . ?
C4 C5 C6 C7 133.1(6) 23 . . . ?
O2 C1 O1 Cu1 -3.8(7) . . . . ?
C2 C1 O1 Cu1 173.1(3) . . . . ?
O2 Cu1 O1 C1 85.6(4) 6 . . . ?
O2 Cu1 O1 C1 1.0(9) 19_655 . . . ?
O1 Cu1 O1 C1 -82.6(4) 24_655 . . . ?
O1W Cu1 O1 C1 179.4(4) . . . . ?
Cu1 Cu1 O1 C1 1.6(3) 19_655 . . . ?
O1 C1 O2 Cu1 4.0(7) . . . 19_655 ?
C2 C1 O2 Cu1 -172.9(3) . . . 19_655 ?
C8 C6 C7 C8 55.5(5) 11 . . . ?
C8 C6 C7 C8 -7.0(5) 25 . . . ?
C7 C6 C7 C8 -70.4(4) 23 . . . ?
C5 C6 C7 C8 175.0(4) . . . . ?
C8 C6 C7 C9 -136.2(4) 11 . . . ?
C8 C6 C7 C9 161.2(5) 25 . . . ?
C7 C6 C7 C9 97.8(4) 23 . . . ?
C5 C6 C7 C9 -16.7(6) . . . . ?
C8 C6 C7 C7 125.9(5) 11 . . 23 ?
C8 C6 C7 C7 63.4(5) 25 . . 23 ?
C5 C6 C7 C7 -114.5(7) . . . 23 ?
C8 C6 C7 C8 -62.6(6) 25 . . 11 ?
C7 C6 C7 C8 -125.9(5) 23 . . 11 ?
C5 C6 C7 C8 119.5(7) . . . 11 ?
C6 C7 C8 C6 7.7(6) . . . 25 ?
C9 C7 C8 C6 -161.3(5) . . . 25 ?
C7 C7 C8 C6 -42.8(5) 23 . . 25 ?
C8 C7 C8 C6 47.1(5) 11 . . 25 ?
C6 C7 C8 C8 50.5(4) . . . 23 ?
C9 C7 C8 C8 -118.4 . . . 23 ?
C7 C7 C8 C8 0.000(2) 23 . . 23 ?
C8 C7 C8 C8 90.0 11 . . 23 ?
C6 C7 C8 C7 -39.5(4) . . . 11 ?
C9 C7 C8 C7 151.538(1) . . . 11 ?
C7 C7 C8 C7 -90.026(2) 23 . . 11 ?
C8 C7 C8 C7 0.0 11 . . 11 ?

# 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 -0.076 -0.057 -0.002 7289 2697 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.156
