# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1056732'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H10 Cu2 N2 O10'
_chemical_formula_weight         565.38

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'
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'
Cu Cu 0.3201 1.2651 '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                   18.8059(3)
_cell_length_b                   18.8059(3)
_cell_length_c                   37.6262(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11524.2(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3249
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2538
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7654
_exptl_absorpt_correction_T_max  0.8752
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32890
_diffrn_reflns_av_R_equivalents  0.1733
_diffrn_reflns_av_unetl/netI     0.0702
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3249
_reflns_number_gt                2346
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.1765P)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       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     95
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2567
_refine_ls_wR_factor_gt          0.2415
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.021
_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 0.37881(4) 0.189403(18) 0.195858(15) 0.0318(3) Uani 1 2 d S . .
O1 O 0.44419(19) 0.1492(2) 0.17148(8) 0.0508(8) Uani 1 1 d . . .
O2 O 0.36669(18) 0.1103(2) 0.12259(8) 0.0518(8) Uani 1 1 d . . .
O1W O 0.4409(4) 0.2204(2) 0.24548(16) 0.092(2) Uani 1 2 d S . .
H1WA H 0.4182 0.2388 0.2592 0.138 Uiso 0.50 1 d PR . .
C1 C 0.4271(2) 0.1210(3) 0.14070(11) 0.0417(9) Uani 1 1 d . . .
C2 C 0.4862(3) 0.1000(3) 0.12331(12) 0.0461(10) Uani 1 1 d . . .
C3 C 0.55738(19) 0.1148(4) 0.14041(16) 0.0420(13) Uani 1 2 d S . .
H3A H 0.5674 0.1348 0.1636 0.050 Uiso 1 2 calc SR . .
C4 C 0.4722(3) 0.0706(4) 0.08789(13) 0.0611(14) Uani 1 1 d . . .
H4A H 0.4245 0.0609 0.0762 0.073 Uiso 1 1 calc R . .
C5 C 0.5282(3) 0.0564(6) 0.0705(2) 0.071(3) Uani 1 2 d S . .
C6 C 0.5126(4) 0.0253(7) 0.0343(2) 0.080(3) Uani 1 2 d SDU . .
C7 C 0.5747(8) 0.0433(10) 0.0128(3) 0.085(4) Uani 0.50 1 d PDU A -1
H7A H 0.6303 0.0765 0.0207 0.102 Uiso 0.50 1 d PR A -1
N1 N 0.4389(9) -0.0191(10) 0.0224(4) 0.100(4) Uani 0.50 1 d PU A -1

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 0.0245(4) 0.0391(4) 0.0269(4) -0.00080(11) -0.0016(2) 0.0123(2)
O1 0.0461(17) 0.074(2) 0.0434(17) -0.0095(15) -0.0022(13) 0.0384(17)
O2 0.0396(16) 0.079(2) 0.0462(17) -0.0134(16) -0.0038(13) 0.0362(16)
O1W 0.091(4) 0.114(4) 0.063(3) -0.0219(17) -0.044(3) 0.046(2)
C1 0.033(2) 0.050(2) 0.040(2) -0.0015(18) 0.0043(16) 0.0198(19)
C2 0.041(2) 0.062(3) 0.042(2) -0.007(2) -0.0017(18) 0.030(2)
C3 0.041(2) 0.051(3) 0.038(3) -0.005(3) -0.0027(13) 0.0255(17)
C4 0.049(3) 0.097(4) 0.052(3) -0.025(3) -0.016(2) 0.047(3)
C5 0.061(3) 0.117(7) 0.053(4) -0.036(4) -0.018(2) 0.058(4)
C6 0.068(3) 0.127(6) 0.066(5) -0.036(5) -0.018(2) 0.064(3)
C7 0.080(7) 0.123(8) 0.066(7) -0.033(6) -0.017(5) 0.062(6)
N1 0.101(7) 0.135(8) 0.079(6) -0.038(6) -0.020(5) 0.071(6)

_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 1.963(3) . ?
Cu1 O1 1.963(3) 23 ?
Cu1 O2 1.963(3) 11 ?
Cu1 O2 1.963(3) 25 ?
Cu1 O1W 2.123(5) . ?
Cu1 Cu1 2.6494(12) 25 ?
O1 C1 1.247(5) . ?
O2 C1 1.252(5) . ?
O2 Cu1 1.963(3) 25 ?
O1W H1WA 0.8458 . ?
C1 C2 1.503(6) . ?
C2 C3 1.382(5) . ?
C2 C4 1.416(6) . ?
C3 C2 1.382(5) 24_655 ?
C3 H3A 0.9300 . ?
C4 C5 1.376(6) . ?
C4 H4A 0.9300 . ?
C5 C4 1.376(6) 24_655 ?
C5 C6 1.452(11) . ?
C6 N1 1.290(15) 24_655 ?
C6 N1 1.290(15) . ?
C6 C7 1.320(13) . ?
C6 C7 1.320(13) 24_655 ?
C7 H7A 0.9599 . ?

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 88.6(2) . 23 ?
O1 Cu1 O2 89.96(16) . 11 ?
O1 Cu1 O2 167.75(13) 23 11 ?
O1 Cu1 O2 167.75(13) . 25 ?
O1 Cu1 O2 89.95(16) 23 25 ?
O2 Cu1 O2 88.9(2) 11 25 ?
O1 Cu1 O1W 98.77(17) . . ?
O1 Cu1 O1W 98.77(17) 23 . ?
O2 Cu1 O1W 93.47(17) 11 . ?
O2 Cu1 O1W 93.47(17) 25 . ?
O1 Cu1 Cu1 85.18(9) . 25 ?
O1 Cu1 Cu1 85.18(9) 23 25 ?
O2 Cu1 Cu1 82.59(9) 11 25 ?
O2 Cu1 Cu1 82.58(9) 25 25 ?
O1W Cu1 Cu1 174.4(2) . 25 ?
C1 O1 Cu1 121.4(3) . . ?
C1 O2 Cu1 124.3(3) . 25 ?
Cu1 O1W H1WA 109.2 . . ?
O1 C1 O2 126.4(4) . . ?
O1 C1 C2 116.7(4) . . ?
O2 C1 C2 116.8(4) . . ?
C3 C2 C4 119.4(4) . . ?
C3 C2 C1 120.9(4) . . ?
C4 C2 C1 119.6(4) . . ?
C2 C3 C2 120.4(6) 24_655 . ?
C2 C3 H3A 119.8 24_655 . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C2 120.8(5) . . ?
C5 C4 H4A 119.6 . . ?
C2 C4 H4A 119.6 . . ?
C4 C5 C4 119.4(7) . 24_655 ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C6 120.3(3) 24_655 . ?
N1 C6 N1 97.5(14) 24_655 . ?
N1 C6 C7 48.9(8) 24_655 . ?
N1 C6 C7 118.7(10) . . ?
N1 C6 C7 118.7(10) 24_655 24_655 ?
N1 C6 C7 48.9(8) . 24_655 ?
C7 C6 C7 98.3(14) . 24_655 ?
N1 C6 C5 121.4(8) 24_655 . ?
N1 C6 C5 121.4(8) . . ?
C7 C6 C5 120.0(8) . . ?
C7 C6 C5 120.0(8) 24_655 . ?
C6 C7 H7A 120.7 . . ?

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
O1 Cu1 O1 C1 -83.8(4) 23 . . . ?
O2 Cu1 O1 C1 84.1(4) 11 . . . ?
O2 Cu1 O1 C1 -0.6(9) 25 . . . ?
O1W Cu1 O1 C1 177.6(4) . . . . ?
Cu1 Cu1 O1 C1 1.5(3) 25 . . . ?
Cu1 O1 C1 O2 -4.2(7) . . . . ?
Cu1 O1 C1 C2 174.0(3) . . . . ?
Cu1 O2 C1 O1 4.9(7) 25 . . . ?
Cu1 O2 C1 C2 -173.2(3) 25 . . . ?
O1 C1 C2 C3 -2.5(7) . . . . ?
O2 C1 C2 C3 175.8(5) . . . . ?
O1 C1 C2 C4 -177.6(5) . . . . ?
O2 C1 C2 C4 0.8(7) . . . . ?
C4 C2 C3 C2 -0.9(10) . . . 24_655 ?
C1 C2 C3 C2 -176.0(4) . . . 24_655 ?
C3 C2 C4 C5 0.3(10) . . . . ?
C1 C2 C4 C5 175.5(7) . . . . ?
C2 C4 C5 C4 0.2(15) . . . 24_655 ?
C2 C4 C5 C6 179.2(8) . . . . ?
C4 C5 C6 N1 -151.2(12) . . . 24_655 ?
C4 C5 C6 N1 27.8(17) 24_655 . . 24_655 ?
C4 C5 C6 N1 -27.8(17) . . . . ?
C4 C5 C6 N1 151.2(12) 24_655 . . . ?
C4 C5 C6 C7 151.3(12) . . . . ?
C4 C5 C6 C7 -29.7(18) 24_655 . . . ?
C4 C5 C6 C7 29.7(18) . . . 24_655 ?
C4 C5 C6 C7 -151.3(12) 24_655 . . 24_655 ?

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 -0.034 -0.022 -0.001 7652 2293
_platon_squeeze_details          
;?
;

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.525
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.211
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1441682'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H5 Cu N O5'
_chemical_formula_weight         282.69

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

_cell_length_a                   18.65700(10)
_cell_length_b                   18.65700(10)
_cell_length_c                   38.0533(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11471.1(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2538
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7764
_exptl_absorpt_correction_T_max  0.9189
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41155
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetl/netI     0.0273
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3211
_reflns_number_gt                2682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0649P)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         3211
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Cu1 Cu 0.856825(7) 0.143175(7) 0.138009(6) 0.02534(11) Uani 1 2 d S . .
O1 O 0.81561(8) 0.03828(7) 0.16283(3) 0.0397(3) Uani 1 1 d . . .
O2 O 0.77533(9) 0.07770(8) 0.21103(3) 0.0448(3) Uani 1 1 d . . .
O1W O 0.88995(7) 0.11005(7) 0.08941(6) 0.0797(7) Uani 1 2 d S . .
H1WA H 0.9094 0.1518 0.0756 0.120 Uiso 0.50 1 d PR . .
C1 C 0.78684(10) 0.02722(10) 0.19355(4) 0.0339(3) Uani 1 1 d . . .
C2 C 0.76538(10) -0.05300(10) 0.21086(4) 0.0369(4) Uani 1 1 d . . .
C3 C 0.73576(12) -0.06803(11) 0.24542(4) 0.0448(4) Uani 1 1 d . . .
H3 H 0.7258 -0.0298 0.2569 0.045(5) Uiso 1 1 calc R . .
C4 C 0.77964(14) -0.11018(7) 0.19391(6) 0.0345(5) Uani 1 2 d S . .
H4 H 0.7990 -0.1005 0.1709 0.033(6) Uiso 1 2 calc SR . .
C5 C 0.72122(18) -0.13939(9) 0.26270(7) 0.0469(7) Uani 1 2 d S . .
C6 C 0.6921(2) -0.15394(11) 0.29970(7) 0.0535(7) Uani 1 2 d S . .
N1 N 0.6480(4) -0.2323(3) 0.31192(11) 0.0658(13) Uani 0.25 1 d P . 1
N1' N 0.7099(4) -0.0881(2) 0.32099(12) 0.0671(13) Uani 0.25 1 d P . 1
C7 C 0.6480(4) -0.2323(3) 0.31192(11) 0.0658(13) Uani 0.25 1 d P . 2
H7A H 0.6312 -0.2790 0.2962 0.079 Uiso 0.25 1 d PR . 2
C7' C 0.7099(4) -0.0881(2) 0.32099(12) 0.0671(13) Uani 0.25 1 d P . 2
H7'A H 0.7375 -0.0330 0.3115 0.080 Uiso 0.25 1 d PR . 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 0.03497(14) 0.03497(14) 0.01849(15) -0.00076(4) 0.00076(4) 0.02680(13)
O1 0.0581(7) 0.0374(6) 0.0324(6) 0.0055(5) 0.0084(5) 0.0306(6)
O2 0.0736(9) 0.0428(7) 0.0350(6) 0.0090(5) 0.0127(6) 0.0418(7)
O1W 0.0895(12) 0.0895(12) 0.0613(13) -0.0245(6) 0.0245(6) 0.0457(14)
C1 0.0435(9) 0.0368(9) 0.0311(8) 0.0019(7) -0.0003(7) 0.0274(8)
C2 0.0487(10) 0.0367(9) 0.0337(8) 0.0045(7) 0.0035(7) 0.0275(8)
C3 0.0684(12) 0.0408(10) 0.0387(9) 0.0053(7) 0.0122(8) 0.0375(9)
C4 0.0417(13) 0.0345(8) 0.0298(11) 0.0010(5) 0.0020(9) 0.0209(6)
C5 0.0717(19) 0.0408(9) 0.0386(14) 0.0084(6) 0.0168(12) 0.0359(9)
C6 0.091(2) 0.0436(9) 0.0417(14) 0.0109(7) 0.0217(15) 0.0456(11)
N1 0.118(4) 0.037(2) 0.045(2) 0.0077(16) 0.030(3) 0.041(3)
N1' 0.116(4) 0.036(2) 0.052(3) 0.0088(18) 0.033(3) 0.040(3)
C7 0.118(4) 0.037(2) 0.045(2) 0.0077(16) 0.030(3) 0.041(3)
C7' 0.116(4) 0.036(2) 0.052(3) 0.0088(18) 0.033(3) 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
Cu1 O1 1.9515(11) . ?
Cu1 O1 1.9515(11) 22_665 ?
Cu1 O2 1.9553(11) 10_545 ?
Cu1 O2 1.9553(11) 25_655 ?
Cu1 O1W 2.1366(18) . ?
Cu1 Cu1 2.6576(4) 25_655 ?
O1 C1 1.2597(18) . ?
O2 C1 1.2561(18) . ?
O2 Cu1 1.9553(11) 25_655 ?
C1 C2 1.495(2) . ?
C2 C4 1.3816(19) . ?
C2 C3 1.399(2) . ?
C3 C5 1.385(2) . ?
C4 C2 1.3816(19) 24_545 ?
C5 C3 1.385(2) 24_545 ?
C5 C6 1.485(4) . ?
C6 N1 1.352(5) . ?
C6 C7 1.352(4) 24_545 ?
C6 N1 1.352(4) 24_545 ?
C6 N1' 1.367(4) . ?
C6 C7' 1.367(4) 24_545 ?
C6 N1' 1.367(4) 24_545 ?
N1 N1' 1.058(6) 24_545 ?
N1 N1' 1.344(5) 31_645 ?
N1 N1 1.738(10) 18_655 ?
N1' N1 1.058(6) 24_545 ?
N1' N1 1.344(5) 31_645 ?
N1' N1' 1.684(9) 18_655 ?

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 88.60(7) . 22_665 ?
O1 Cu1 O2 89.87(6) . 10_545 ?
O1 Cu1 O2 167.76(5) 22_665 10_545 ?
O1 Cu1 O2 167.76(5) . 25_655 ?
O1 Cu1 O2 89.87(6) 22_665 25_655 ?
O2 Cu1 O2 89.05(8) 10_545 25_655 ?
O1 Cu1 O1W 98.90(6) . . ?
O1 Cu1 O1W 98.90(6) 22_665 . ?
O2 Cu1 O1W 93.34(6) 10_545 . ?
O2 Cu1 O1W 93.34(6) 25_655 . ?
O1 Cu1 Cu1 84.49(3) . 25_655 ?
O1 Cu1 Cu1 84.49(3) 22_665 25_655 ?
O2 Cu1 Cu1 83.27(3) 10_545 25_655 ?
O2 Cu1 Cu1 83.27(3) 25_655 25_655 ?
O1W Cu1 Cu1 175.22(7) . 25_655 ?
C1 O1 Cu1 122.37(10) . . ?
C1 O2 Cu1 123.70(10) . 25_655 ?
O2 C1 O1 125.96(15) . . ?
O2 C1 C2 117.18(13) . . ?
O1 C1 C2 116.86(13) . . ?
C4 C2 C3 119.56(15) . . ?
C4 C2 C1 120.58(14) . . ?
C3 C2 C1 119.73(14) . . ?
C5 C3 C2 120.44(16) . . ?
C2 C4 C2 120.6(2) . 24_545 ?
C3 C5 C3 119.4(2) 24_545 . ?
C3 C5 C6 120.27(11) 24_545 . ?
C3 C5 C6 120.27(11) . . ?
N1 C6 C7 102.0(5) . 24_545 ?
N1 C6 N1 102.0(5) . 24_545 ?
C7 C6 N1 0.0(4) 24_545 24_545 ?
N1 C6 N1' 120.8(3) . . ?
C7 C6 N1' 45.8(3) 24_545 . ?
N1 C6 N1' 45.8(3) 24_545 . ?
N1 C6 C7' 45.8(3) . 24_545 ?
C7 C6 C7' 120.8(3) 24_545 24_545 ?
N1 C6 C7' 120.8(3) 24_545 24_545 ?
N1' C6 C7' 102.1(5) . 24_545 ?
N1 C6 N1' 45.8(3) . 24_545 ?
C7 C6 N1' 120.8(3) 24_545 24_545 ?
N1 C6 N1' 120.8(3) 24_545 24_545 ?
N1' C6 N1' 102.1(5) . 24_545 ?
C7' C6 N1' 0.0(4) 24_545 24_545 ?
N1 C6 C5 119.5(2) . . ?
C7 C6 C5 119.5(2) 24_545 . ?
N1 C6 C5 119.5(2) 24_545 . ?
N1' C6 C5 119.7(2) . . ?
C7' C6 C5 119.7(2) 24_545 . ?
N1' C6 C5 119.7(2) 24_545 . ?
N1' N1 N1' 88.1(6) 24_545 31_645 ?
N1' N1 C6 67.8(4) 24_545 . ?
N1' N1 C6 119.4(4) 31_645 . ?
N1' N1 N1 50.6(4) 24_545 18_655 ?
N1' N1 N1 37.5(3) 31_645 18_655 ?
C6 N1 N1 98.0(4) . 18_655 ?
N1 N1' N1 91.9(6) 24_545 31_645 ?
N1 N1' C6 66.4(4) 24_545 . ?
N1 N1' C6 119.8(4) 31_645 . ?
N1 N1' N1' 52.9(4) 24_545 18_655 ?
N1 N1' N1' 38.9(3) 31_645 18_655 ?
C6 N1' N1' 99.0(4) . 18_655 ?
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 -0.036 -0.023 -0.001 7789.1 1004.2
_platon_squeeze_details          
; ?
;
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.059
