# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1037351'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'C19 H9 N2 O10 Zn2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 N2 O10 Zn2'
_chemical_formula_sum            'C19 H9 N2 O10 Zn2'
_chemical_formula_weight         556.02

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P42/nnm

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

_cell_length_a                   17.7349(6)
_cell_length_b                   17.7349(6)
_cell_length_c                   28.1732(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8861.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.2

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2216
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8002
_exptl_absorpt_correction_T_max  0.8250
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            106509
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         28.40
_reflns_number_total             5816
_reflns_number_gt                4216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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)+(0.1089P)²+8.4866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5816
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2089
_refine_ls_wR_factor_gt          0.1860
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
C009 C 0.4636(2) 0.1851(2) 0.07981(15) 0.0414(10) Uani 1 1 d . . .
C010 C 0.4148(2) 0.1862(2) 0.11809(14) 0.0408(9) Uani 1 1 d . . .
H010 H 0.3876 0.1418 0.1260 0.049 Uiso 1 1 calc R . .
C011 C 0.4445(3) 0.3160(3) 0.13324(15) 0.0482(11) Uani 1 1 d . . .
H011 H 0.4383 0.3609 0.1512 0.058 Uiso 1 1 calc R . .
C012 C 0.5918(3) 0.4082(3) 0.1035(3) 0.071(2) Uani 1 2 d S . .
H012 H 0.6120 0.3880 0.1320 0.086 Uiso 1 2 calc SR . .
C014 C 0.4918(2) 0.3138(2) 0.09561(15) 0.0459(10) Uani 1 1 d . . .
C015 C 0.5023(3) 0.2500(2) 0.06850(16) 0.0489(11) Uani 1 1 d . . .
H015 H 0.5360 0.2508 0.0423 0.059 Uiso 1 1 calc R . .
C016 C 0.5355(5) 0.4124(5) 0.0392(3) 0.154(4) Uani 1 1 d . . .
H016 H 0.5039 0.3993 0.0133 0.184 Uiso 1 1 calc R . .
C017 C 0.3503(2) 0.2508(3) 0.18547(16) 0.0436(10) Uani 1 1 d . . .
C018 C 0.4747(3) 0.1156(3) 0.05055(16) 0.0463(10) Uani 1 1 d . . .
C20 C 0.4048(2) 0.2503(2) 0.14510(14) 0.0411(9) Uani 1 1 d . . .
O2 O 0.6124(2) 0.1124(2) -0.0755(2) 0.0877(18) Uani 1 2 d S . .
N008 N 0.5348(2) 0.3806(2) 0.08287(14) 0.0570(11) Uani 1 1 d . . .
O1 O 0.5120(2) 0.12238(18) 0.01354(11) 0.0617(9) Uani 1 1 d . . .
O6 O 0.44496(19) 0.05594(17) 0.06626(11) 0.0555(8) Uani 1 1 d . . .
O3 O 0.31736(17) 0.18975(17) 0.19427(9) 0.0474(7) Uani 1 1 d . . .
O4 O 0.33925(17) 0.31238(17) 0.20667(10) 0.0480(8) Uani 1 1 d . . .
Zn1 Zn 0.54554(2) 0.04554(2) -0.03503(2) 0.02934(19) Uani 1 2 d S . .
Zn2 Zn 0.2500 0.16545(3) 0.2500 0.03037(19) Uani 1 2 d S . .
O5 O 0.2500 0.0495(4) 0.2500 0.111(2) Uani 1 2 d S . .


_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
C009 C015 1.378(6) . ?
C009 C010 1.383(6) . ?
C009 C018 1.496(6) . ?
C010 C20 1.380(5) . ?
C011 C014 1.353(6) . ?
C011 C20 1.401(6) . ?
C012 N008 1.264(6) . ?
C012 N008 1.264(6) 15_665 ?
C014 C015 1.378(6) . ?
C014 N008 1.453(5) . ?
C016 C016 1.305(13) 15_665 ?
C016 N008 1.353(8) . ?
C017 O4 1.260(5) . ?
C017 O3 1.255(5) . ?
C017 C20 1.492(6) . ?
C018 O1 1.241(5) . ?
C018 O6 1.262(5) . ?
O2 Zn1 2.028(5) . ?
O1 Zn1 2.021(3) . ?
O6 Zn1 2.010(3) 9_655 ?
O3 Zn2 2.019(3) . ?
O4 Zn2 2.037(3) 3 ?
Zn1 O6 2.010(3) 9_655 ?
Zn1 O6 2.010(3) 8 ?
Zn1 O1 2.021(3) 16_655 ?
Zn1 Zn1 3.0186(11) 9_655 ?
Zn2 O3 2.019(3) 6 ?
Zn2 O4 2.037(3) 3 ?
Zn2 O4 2.037(3) 5 ?
Zn2 O5 2.056(7) . ?
Zn2 Zn2 2.9990(11) 3 ?

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
C015 C009 C010 118.8(4) . . ?
C015 C009 C018 119.7(4) . . ?
C010 C009 C018 121.5(4) . . ?
C20 C010 C009 121.5(4) . . ?
C014 C011 C20 118.4(4) . . ?
N008 C012 N008 114.1(8) . 15_665 ?
C011 C014 C015 122.8(4) . . ?
C011 C014 N008 119.8(4) . . ?
C015 C014 N008 117.5(4) . . ?
C009 C015 C014 119.4(4) . . ?
C016 C016 N008 107.6(3) 15_665 . ?
O4 C017 O3 125.6(4) . . ?
O4 C017 C20 117.8(4) . . ?
O3 C017 C20 116.6(4) . . ?
O1 C018 O6 126.7(4) . . ?
O1 C018 C009 117.0(4) . . ?
O6 C018 C009 116.3(4) . . ?
C010 C20 C011 119.2(4) . . ?
C010 C20 C017 120.6(4) . . ?
C011 C20 C017 120.1(4) . . ?
C012 N008 C016 104.3(5) . . ?
C012 N008 C014 128.4(5) . . ?
C016 N008 C014 124.7(4) . . ?
C018 O1 Zn1 131.4(3) . . ?
C018 O6 Zn1 124.2(3) . 9_655 ?
C017 O3 Zn2 127.8(3) . . ?
C017 O4 Zn2 124.9(3) . 3 ?
O6 Zn1 O6 87.6(2) 9_655 8 ?
O6 Zn1 O1 157.64(14) 9_655 . ?
O6 Zn1 O1 88.63(14) 8 . ?
O6 Zn1 O1 88.63(14) 9_655 16_655 ?
O6 Zn1 O1 157.64(14) 8 16_655 ?
O1 Zn1 O1 86.5(2) . 16_655 ?
O6 Zn1 O2 103.19(15) 9_655 . ?
O6 Zn1 O2 103.19(15) 8 . ?
O1 Zn1 O2 99.13(15) . . ?
O1 Zn1 O2 99.13(15) 16_655 . ?
O6 Zn1 Zn1 81.49(10) 9_655 9_655 ?
O6 Zn1 Zn1 81.49(10) 8 9_655 ?
O1 Zn1 Zn1 76.15(10) . 9_655 ?
O1 Zn1 Zn1 76.15(10) 16_655 9_655 ?
O2 Zn1 Zn1 173.39(17) . 9_655 ?
O3 Zn2 O3 155.35(18) . 6 ?
O3 Zn2 O4 87.28(12) . 3 ?
O3 Zn2 O4 88.00(12) 6 3 ?
O3 Zn2 O4 88.00(12) . 5 ?
O3 Zn2 O4 87.28(12) 6 5 ?
O4 Zn2 O4 157.74(17) 3 5 ?
O3 Zn2 O5 102.32(9) . . ?
O3 Zn2 O5 102.32(9) 6 . ?
O4 Zn2 O5 101.13(9) 3 . ?
O4 Zn2 O5 101.13(9) 5 . ?
O3 Zn2 Zn2 77.68(9) . 3 ?
O3 Zn2 Zn2 77.68(9) 6 3 ?
O4 Zn2 Zn2 78.87(9) 3 3 ?
O4 Zn2 Zn2 78.87(9) 5 3 ?
O5 Zn2 Zn2 180.0 . 3 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.177
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.102
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.007 0.790 0.049 5872.3 912.5
_platon_squeeze_details          
; ?
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-MeCN
_database_code_depnum_ccdc_archive 'CCDC 1037352'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 N2 O10 Zn2'
_chemical_formula_sum            'C19 H9 N2 O10 Zn2'
_chemical_formula_weight         556.02

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I41/amd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z'
'-x, y+1/2, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z'
'x, -y-1/2, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   25.5552(11)
_cell_length_b                   25.5552(11)
_cell_length_c                   51.403(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     33570(3)
_cell_formula_units_Z            32
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.880
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             8864
_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7907
_exptl_absorpt_correction_T_max  0.8166
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            131694
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7752
_reflns_number_gt                5222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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)+(0.1656P)²+257.4813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7752
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.3065
_refine_ls_wR_factor_gt          0.2784
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
Zn1 Zn 0.22712(4) 0.43927(4) 0.126642(19) 0.0477(3) Uani 1 1 d . . .
Zn2 Zn 0.27900(4) 0.7500 0.03325(2) 0.0402(4) Uani 1 2 d S . .
Zn3 Zn 0.19784(5) 0.7500 -0.00923(2) 0.0388(4) Uani 1 2 d S . .
O1 O 0.2769(2) 0.4079(2) 0.15229(11) 0.0585(16) Uani 1 1 d . . .
C2 C 0.1882(3) 0.6766(3) 0.03323(18) 0.052(2) Uani 1 1 d . . .
O3 O 0.1864(2) 0.4822(2) 0.10150(12) 0.0598(16) Uani 1 1 d . . .
N6 N 0.0414(3) 0.5515(3) 0.04470(13) 0.0503(17) Uani 1 1 d . . .
O7 O 0.2742(2) 0.4171(2) 0.09669(11) 0.0586(16) Uani 1 1 d . . .
O8 O 0.1659(2) 0.6950(3) 0.01370(12) 0.0634(16) Uani 1 1 d . . .
O9 O 0.2276(3) 0.6941(3) 0.04406(13) 0.0711(18) Uani 1 1 d . . .
C10 C 0.1644(3) 0.6286(4) 0.04539(16) 0.052(2) Uani 1 1 d . . .
C11 C 0.1941(3) 0.5991(3) 0.06231(15) 0.047(2) Uani 1 1 d . . .
H11 H 0.2286 0.6102 0.0664 0.057 Uiso 1 1 calc R . .
C12 C 0.3384(4) 0.4127(3) 0.18622(18) 0.056(2) Uani 1 1 d . . .
C14 C 0.3144(3) 0.4337(3) 0.16215(16) 0.047(2) Uani 1 1 d . . .
C15 C 0.2079(3) 0.5224(4) 0.09172(17) 0.052(2) Uani 1 1 d . . .
C16 C 0.3727(4) 0.4414(3) 0.19991(17) 0.053(2) Uani 1 1 d . . .
H16 H 0.3831 0.4745 0.1933 0.064 Uiso 1 1 calc R . .
C17 C 0.1146(3) 0.6128(3) 0.03893(17) 0.052(2) Uani 1 1 d . . .
H17 H 0.0941 0.6325 0.0270 0.063 Uiso 1 1 calc R . .
C18 C 0.1747(3) 0.5539(3) 0.07334(17) 0.049(2) Uani 1 1 d . . .
C19 C 0.3445(6) 0.2500 0.2115(2) 0.056(3) Uani 1 2 d S . .
H19 H 0.3561 0.2500 0.1940 0.068 Uiso 1 2 calc SR . .
C20 C 0.0948(3) 0.5673(4) 0.05025(18) 0.054(2) Uani 1 1 d . . .
C21 C 0.1242(3) 0.5371(4) 0.06710(16) 0.052(2) Uani 1 1 d . . .
H21 H 0.1105 0.5057 0.0742 0.062 Uiso 1 1 calc R . .
N22 N 0.3350(4) 0.2919(3) 0.22588(16) 0.075(3) Uani 1 1 d . . .
C23 C 0.0000 0.5794(5) 0.0504(2) 0.041(3) Uani 1 2 d S . .
H23 H 0.0000 0.6137 0.0575 0.049 Uiso 1 2 calc SR . .
O25 O 0.1727(3) 0.3822(3) 0.13019(17) 0.103(3) Uani 1 1 d . . .
O26 O 0.3287(4) 0.7500 0.06228(18) 0.081(3) Uani 1 2 d S . .
C27 C 0.3189(6) 0.2752(4) 0.2512(2) 0.099(4) Uani 1 1 d . . .
H27 H 0.3099 0.2972 0.2654 0.119 Uiso 1 1 calc R . .
C28 C 0.3802(4) 0.3747(4) 0.23237(19) 0.068(3) Uani 1 1 d . . .
H28 H 0.3940 0.3618 0.2483 0.082 Uiso 1 1 calc R . .
C29 C 0.0262(3) 0.5034(4) 0.03566(18) 0.064(2) Uani 1 1 d . . .
H29 H 0.0485 0.4755 0.0304 0.076 Uiso 1 1 calc R . .
C30 C 0.3936(4) 0.4243(3) 0.22359(18) 0.057(2) Uani 1 1 d . . .
C32 C 0.3247(4) 0.3626(3) 0.19513(18) 0.063(3) Uani 1 1 d . . .
H32 H 0.3004 0.3420 0.1856 0.076 Uiso 1 1 calc R . .
C33 C 0.3460(5) 0.3437(3) 0.21739(18) 0.070(3) Uani 1 1 d . . .
O38 O 0.1489(6) 0.7500 -0.0399(2) 0.110(4) Uani 1 2 d S . .
O4 O 0.2505(3) 0.8053(3) -0.02101(13) 0.0643(17) Uani 1 1 d . . .
O2 O 0.2523(2) 0.5375(3) 0.09564(12) 0.0590(16) Uani 1 1 d . . .
O5 O 0.3121(3) 0.6970(4) 0.01018(15) 0.101(3) Uani 1 1 d . . .
C4 C 0.4309(4) 0.4579(4) 0.2382(2) 0.064(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.989(6) . ?
Zn1 O1 2.000(5) . ?
Zn1 O25 2.024(7) . ?
Zn1 O7 2.034(5) . ?
Zn1 O2 2.098(6) 16_554 ?
Zn1 Zn1 3.0266(18) 16_554 ?
Zn2 O26 1.959(8) . ?
Zn2 O5 1.990(7) 22_575 ?
Zn2 O5 1.990(7) . ?
Zn2 O9 2.020(6) . ?
Zn2 O9 2.020(6) 22_575 ?
Zn2 Zn3 3.0114(16) . ?
Zn3 O8 2.008(6) 22_575 ?
Zn3 O8 2.008(6) . ?
Zn3 O38 2.014(10) . ?
Zn3 O4 2.044(6) . ?
Zn3 O4 2.044(6) 22_575 ?
O1 C14 1.269(10) . ?
C2 O9 1.234(11) . ?
C2 O8 1.246(10) . ?
C2 C10 1.504(12) . ?
O3 C15 1.268(10) . ?
N6 C23 1.309(10) . ?
N6 C29 1.371(12) . ?
N6 C20 1.452(10) . ?
O7 C14 1.259(10) 16_554 ?
C10 C11 1.379(11) . ?
C10 C17 1.377(12) . ?
C11 C18 1.380(12) . ?
C12 C16 1.341(12) . ?
C12 C32 1.405(13) . ?
C12 C14 1.481(12) . ?
C14 O7 1.259(10) 16_554 ?
C15 O2 1.214(10) . ?
C15 C18 1.504(12) . ?
C16 C30 1.400(12) . ?
C17 C20 1.394(12) . ?
C18 C21 1.397(11) . ?
C19 N22 1.323(11) 22_565 ?
C19 N22 1.323(11) . ?
C20 C21 1.382(12) . ?
N22 C33 1.420(12) . ?
N22 C27 1.431(15) . ?
C23 N6 1.309(10) 21 ?
C27 C27 1.29(2) 22_565 ?
C28 C30 1.388(13) . ?
C28 C33 1.409(13) . ?
C29 C29 1.340(18) 21 ?
C30 C4 1.487(12) . ?
C32 C33 1.357(12) . ?
O4 C4 1.217(12) 23_675 ?
O2 Zn1 2.098(6) 16_554 ?
O5 C4 1.304(12) 10_544 ?
C4 O4 1.217(12) 31_665 ?
C4 O5 1.304(12) 12_454 ?

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
O3 Zn1 O1 169.1(3) . . ?
O3 Zn1 O25 95.6(3) . . ?
O1 Zn1 O25 95.1(3) . . ?
O3 Zn1 O7 88.3(3) . . ?
O1 Zn1 O7 90.6(3) . . ?
O25 Zn1 O7 105.9(3) . . ?
O3 Zn1 O2 87.4(3) . 16_554 ?
O1 Zn1 O2 87.2(2) . 16_554 ?
O25 Zn1 O2 109.3(3) . 16_554 ?
O7 Zn1 O2 144.8(3) . 16_554 ?
O3 Zn1 Zn1 86.74(19) . 16_554 ?
O1 Zn1 Zn1 82.56(18) . 16_554 ?
O25 Zn1 Zn1 177.6(3) . 16_554 ?
O7 Zn1 Zn1 74.72(18) . 16_554 ?
O2 Zn1 Zn1 70.17(17) 16_554 16_554 ?
O26 Zn2 O5 100.3(3) . 22_575 ?
O26 Zn2 O5 100.3(3) . . ?
O5 Zn2 O5 85.9(6) 22_575 . ?
O26 Zn2 O9 102.2(3) . . ?
O5 Zn2 O9 157.4(3) 22_575 . ?
O5 Zn2 O9 87.6(3) . . ?
O26 Zn2 O9 102.2(3) . 22_575 ?
O5 Zn2 O9 87.6(3) 22_575 22_575 ?
O5 Zn2 O9 157.4(3) . 22_575 ?
O9 Zn2 O9 90.1(4) . 22_575 ?
O26 Zn2 Zn3 176.8(3) . . ?
O5 Zn2 Zn3 82.0(2) 22_575 . ?
O5 Zn2 Zn3 82.0(2) . . ?
O9 Zn2 Zn3 75.62(19) . . ?
O9 Zn2 Zn3 75.62(19) 22_575 . ?
O8 Zn3 O8 88.9(4) 22_575 . ?
O8 Zn3 O38 102.0(4) 22_575 . ?
O8 Zn3 O38 102.0(4) . . ?
O8 Zn3 O4 87.6(3) 22_575 . ?
O8 Zn3 O4 157.8(3) . . ?
O38 Zn3 O4 100.2(4) . . ?
O8 Zn3 O4 157.8(3) 22_575 22_575 ?
O8 Zn3 O4 87.6(3) . 22_575 ?
O38 Zn3 O4 100.2(4) . 22_575 ?
O4 Zn3 O4 87.5(4) . 22_575 ?
O8 Zn3 Zn2 81.63(19) 22_575 . ?
O8 Zn3 Zn2 81.63(19) . . ?
O38 Zn3 Zn2 174.8(4) . . ?
O4 Zn3 Zn2 76.19(19) . . ?
O4 Zn3 Zn2 76.19(19) 22_575 . ?
C14 O1 Zn1 122.4(5) . . ?
O9 C2 O8 126.9(8) . . ?
O9 C2 C10 115.9(8) . . ?
O8 C2 C10 117.2(8) . . ?
C15 O3 Zn1 118.5(6) . . ?
C23 N6 C29 109.5(7) . . ?
C23 N6 C20 124.4(8) . . ?
C29 N6 C20 125.6(7) . . ?
C14 O7 Zn1 132.4(6) 16_554 . ?
C2 O8 Zn3 123.4(6) . . ?
C2 O9 Zn2 131.5(6) . . ?
C11 C10 C17 120.1(8) . . ?
C11 C10 C2 119.0(7) . . ?
C17 C10 C2 120.9(8) . . ?
C10 C11 C18 121.3(7) . . ?
C16 C12 C32 119.3(8) . . ?
C16 C12 C14 120.8(8) . . ?
C32 C12 C14 119.9(8) . . ?
O1 C14 O7 125.6(8) . 16_554 ?
O1 C14 C12 117.3(7) . . ?
O7 C14 C12 117.1(8) 16_554 . ?
O2 C15 O3 126.6(8) . . ?
O2 C15 C18 117.4(8) . . ?
O3 C15 C18 116.0(8) . . ?
C12 C16 C30 122.4(8) . . ?
C10 C17 C20 118.6(8) . . ?
C21 C18 C11 119.7(8) . . ?
C21 C18 C15 120.0(8) . . ?
C11 C18 C15 120.3(7) . . ?
N22 C19 N22 108.2(11) 22_565 . ?
C21 C20 C17 122.1(8) . . ?
C21 C20 N6 118.6(8) . . ?
C17 C20 N6 119.3(8) . . ?
C20 C21 C18 118.2(8) . . ?
C19 N22 C33 123.1(9) . . ?
C19 N22 C27 108.5(8) . . ?
C33 N22 C27 128.0(8) . . ?
N6 C23 N6 107.9(11) 21 . ?
C27 C27 N22 107.4(5) 22_565 . ?
C30 C28 C33 119.3(9) . . ?
C29 C29 N6 106.5(5) 21 . ?
C28 C30 C16 118.2(8) . . ?
C28 C30 C4 121.4(9) . . ?
C16 C30 C4 120.3(9) . . ?
C33 C32 C12 120.0(8) . . ?
C32 C33 N22 120.8(8) . . ?
C32 C33 C28 120.6(8) . . ?
N22 C33 C28 118.6(8) . . ?
C4 O4 Zn3 131.3(6) 23_675 . ?
C15 O2 Zn1 136.1(6) . 16_554 ?
C4 O5 Zn2 124.3(7) 10_544 . ?
O4 C4 O5 126.1(9) 31_665 12_454 ?
O4 C4 C30 119.5(9) 31_665 . ?
O5 C4 C30 114.4(10) 12_454 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.537
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.153
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.022 0.141 0.002 21844.2 5326.7
_platon_squeeze_details          
; ?
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-DCM
_database_code_depnum_ccdc_archive 'CCDC 1037353'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 N2 O10 Zn2'
_chemical_formula_sum            'C19 H9 N2 O10 Zn2'
_chemical_formula_weight         556.02

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I41/amd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z'
'-x, y+1/2, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z'
'x, -y-1/2, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   25.4440(14)
_cell_length_b                   25.4440(14)
_cell_length_c                   53.616(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     34711(3)
_cell_formula_units_Z            32
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             8864
_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7966
_exptl_absorpt_correction_T_max  0.8218
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            136958
_diffrn_reflns_av_R_equivalents  0.1523
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.00
_reflns_number_total             9913
_reflns_number_gt                6070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9913
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Zn1 Zn 0.28215(3) 0.7500 0.027474(14) 0.0334(2) Uani 1 2 d S . .
Zn2 Zn 0.19680(3) 0.7500 -0.010916(13) 0.0328(2) Uani 1 2 d S . .
Zn3 Zn 0.22329(2) 0.44460(2) 0.126796(10) 0.03988(18) Uani 1 1 d . . .
O2 O 0.27730(14) 0.41182(12) 0.14975(6) 0.0492(9) Uani 1 1 d . . .
C3 C 0.3129(2) 0.4387(2) 0.16016(10) 0.0518(14) Uani 1 1 d . . .
O4 O 0.24737(14) 0.80600(14) -0.02417(6) 0.0522(9) Uani 1 1 d . . .
O6 O 0.26597(12) 0.42103(14) 0.09728(6) 0.0474(9) Uani 1 1 d . . .
C7 C 0.1891(2) 0.6767(2) 0.03065(11) 0.0500(14) Uani 1 1 d . . .
O8 O 0.16653(13) 0.69525(14) 0.01205(7) 0.0553(10) Uani 1 1 d . . .
N9 N 0.04220(15) 0.55683(17) 0.04645(9) 0.0538(12) Uani 1 1 d . . .
O10 O 0.20401(16) 0.49583(14) 0.15509(7) 0.0630(11) Uani 1 1 d . . .
O11 O 0.16546(17) 0.39097(17) 0.13121(9) 0.0878(14) Uani 1 1 d . . .
C12 C 0.20750(19) 0.5321(2) 0.09201(10) 0.0523(14) Uani 1 1 d . . .
O13 O 0.23206(15) 0.69538(16) 0.03973(8) 0.0742(12) Uani 1 1 d . . .
C14 C 0.3717(2) 0.44697(18) 0.19756(9) 0.0500(14) Uani 1 1 d . . .
H14 H 0.3785 0.4824 0.1930 0.060 Uiso 1 1 calc R . .
N15 N 0.3401(2) 0.29140(15) 0.21826(8) 0.0608(14) Uani 1 1 d . . .
C16 C 0.3827(2) 0.37508(18) 0.22577(10) 0.0564(15) Uani 1 1 d . . .
H16 H 0.3977 0.3606 0.2405 0.068 Uiso 1 1 calc R . .
C17 C 0.12510(18) 0.54398(18) 0.06778(9) 0.0474(13) Uani 1 1 d . . .
H17 H 0.1113 0.5132 0.0753 0.057 Uiso 1 1 calc R . .
C18 C 0.11566(18) 0.61477(19) 0.03818(10) 0.0499(14) Uani 1 1 d . . .
H18 H 0.0952 0.6322 0.0259 0.060 Uiso 1 1 calc R . .
C19 C 0.2897(2) 0.8198(2) -0.01641(10) 0.0555(15) Uani 1 1 d . . .
C20 C 0.3277(2) 0.36447(19) 0.18936(9) 0.0532(14) Uani 1 1 d . . .
H20 H 0.3058 0.3427 0.1793 0.064 Uiso 1 1 calc R . .
C21 C 0.16665(19) 0.63151(19) 0.04368(10) 0.0489(13) Uani 1 1 d . . .
C22 C 0.3382(2) 0.41568(18) 0.18218(8) 0.0430(12) Uani 1 1 d . . .
O23 O 0.31081(16) 0.69673(18) 0.00394(9) 0.0918(15) Uani 1 1 d . . .
C24 C 0.19668(19) 0.60365(19) 0.06190(10) 0.0510(14) Uani 1 1 d . . .
H24 H 0.2313 0.6148 0.0659 0.061 Uiso 1 1 calc R . .
C25 C 0.3491(3) 0.2500 0.20462(12) 0.056(2) Uani 1 2 d S . .
H25 H 0.3603 0.2500 0.1877 0.067 Uiso 1 2 calc SR . .
C26 C 0.3491(2) 0.34525(18) 0.21111(10) 0.0513(14) Uani 1 1 d . . .
C27 C 0.17573(18) 0.5613(2) 0.07354(10) 0.0479(13) Uani 1 1 d . . .
C28 C 0.09582(17) 0.5721(2) 0.05113(10) 0.0504(14) Uani 1 1 d . . .
C29 C 0.3234(4) 0.2771(2) 0.24354(11) 0.121(3) Uani 1 1 d . . .
H29 H 0.3146 0.3000 0.2569 0.146 Uiso 1 1 calc R . .
C30 C 0.0302(3) 0.5077(3) 0.03989(18) 0.125(3) Uani 1 1 d . . .
H30 H 0.0534 0.4796 0.0361 0.149 Uiso 1 1 calc R . .
C31 C 0.0000 0.5835(3) 0.04957(16) 0.059(2) Uani 1 2 d S . .
H31 H 0.0000 0.6198 0.0538 0.071 Uiso 1 2 calc SR . .
O33 O 0.1428(2) 0.7500 -0.03778(12) 0.096(2) Uani 1 2 d S . .
C37 C 0.3942(2) 0.42710(19) 0.21865(9) 0.0477(13) Uani 1 1 d . . .
O43 O 0.3338(2) 0.7500 0.05399(11) 0.102(2) Uani 1 2 d S . .
O1 O 0.18501(13) 0.49495(17) 0.10366(7) 0.0700(12) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O43 1.937(5) . ?
Zn1 O23 1.990(4) . ?
Zn1 O23 1.990(4) 22_575 ?
Zn1 O13 1.997(4) . ?
Zn1 O13 1.997(4) 22_575 ?
Zn1 Zn2 2.9921(10) . ?
Zn2 O33 1.990(5) . ?
Zn2 O8 2.012(3) 22_575 ?
Zn2 O8 2.012(3) . ?
Zn2 O4 2.047(3) . ?
Zn2 O4 2.047(3) 22_575 ?
Zn3 O6 2.011(3) . ?
Zn3 O11 2.021(4) . ?
Zn3 O2 2.025(3) . ?
Zn3 O1 2.032(3) . ?
Zn3 O10 2.060(3) . ?
Zn3 Zn3 2.9609(11) 16_554 ?
O2 C3 1.265(6) . ?
C3 O6 1.287(6) 16_554 ?
C3 C22 1.466(7) . ?
O4 C19 1.206(6) . ?
O6 C3 1.287(6) 16_554 ?
C7 O8 1.245(6) . ?
C7 O13 1.287(6) . ?
C7 C21 1.462(7) . ?
N9 C31 1.282(6) . ?
N9 C30 1.333(8) . ?
N9 C28 1.440(6) . ?
O10 C12 1.248(6) 16_554 ?
C12 O10 1.248(6) 16_554 ?
C12 O1 1.270(6) . ?
C12 C27 1.478(7) . ?
C14 C37 1.365(7) . ?
C14 C22 1.429(6) . ?
N15 C25 1.303(6) . ?
N15 C26 1.441(6) . ?
N15 C29 1.466(7) . ?
C16 C26 1.387(7) . ?
C16 C37 1.408(7) . ?
C17 C28 1.365(6) . ?
C17 C27 1.396(6) . ?
C18 C28 1.385(6) . ?
C18 C21 1.397(6) . ?
C19 O23 1.287(6) 22_575 ?
C19 C37 1.482(7) 23_675 ?
C20 C26 1.377(7) . ?
C20 C22 1.385(6) . ?
C21 C24 1.429(6) . ?
O23 C19 1.287(6) 22_575 ?
C24 C27 1.354(6) . ?
C25 N15 1.303(6) 22_565 ?
C29 C29 1.380(10) 22_565 ?
C30 C30 1.538(14) 21 ?
C31 N9 1.282(6) 21 ?
C37 C19 1.482(7) 31_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
O43 Zn1 O23 102.5(2) . . ?
O43 Zn1 O23 102.5(2) . 22_575 ?
O23 Zn1 O23 85.8(3) . 22_575 ?
O43 Zn1 O13 101.07(19) . . ?
O23 Zn1 O13 88.19(19) . . ?
O23 Zn1 O13 156.41(19) 22_575 . ?
O43 Zn1 O13 101.07(19) . 22_575 ?
O23 Zn1 O13 156.41(19) . 22_575 ?
O23 Zn1 O13 88.19(19) 22_575 22_575 ?
O13 Zn1 O13 88.2(2) . 22_575 ?
O43 Zn1 Zn2 176.2(2) . . ?
O23 Zn1 Zn2 80.20(14) . . ?
O23 Zn1 Zn2 80.20(14) 22_575 . ?
O13 Zn1 Zn2 76.30(12) . . ?
O13 Zn1 Zn2 76.30(12) 22_575 . ?
O33 Zn2 O8 100.28(18) . 22_575 ?
O33 Zn2 O8 100.28(18) . . ?
O8 Zn2 O8 87.6(2) 22_575 . ?
O33 Zn2 O4 100.53(18) . . ?
O8 Zn2 O4 88.35(14) 22_575 . ?
O8 Zn2 O4 159.19(15) . . ?
O33 Zn2 O4 100.53(18) . 22_575 ?
O8 Zn2 O4 159.19(15) 22_575 22_575 ?
O8 Zn2 O4 88.35(14) . 22_575 ?
O4 Zn2 O4 88.2(2) . 22_575 ?
O33 Zn2 Zn1 177.1(2) . . ?
O8 Zn2 Zn1 81.77(11) 22_575 . ?
O8 Zn2 Zn1 81.77(11) . . ?
O4 Zn2 Zn1 77.44(10) . . ?
O4 Zn2 Zn1 77.44(10) 22_575 . ?
O6 Zn3 O11 106.50(16) . . ?
O6 Zn3 O2 89.37(14) . . ?
O11 Zn3 O2 98.32(16) . . ?
O6 Zn3 O1 88.08(15) . . ?
O11 Zn3 O1 98.53(17) . . ?
O2 Zn3 O1 162.99(16) . . ?
O6 Zn3 O10 153.79(15) . . ?
O11 Zn3 O10 99.65(17) . . ?
O2 Zn3 O10 88.55(14) . . ?
O1 Zn3 O10 86.35(17) . . ?
O6 Zn3 Zn3 77.18(10) . 16_554 ?
O11 Zn3 Zn3 176.31(14) . 16_554 ?
O2 Zn3 Zn3 81.45(10) . 16_554 ?
O1 Zn3 Zn3 81.58(11) . 16_554 ?
O10 Zn3 Zn3 76.66(11) . 16_554 ?
C3 O2 Zn3 122.1(3) . . ?
O2 C3 O6 125.1(5) . 16_554 ?
O2 C3 C22 116.9(5) . . ?
O6 C3 C22 117.9(5) 16_554 . ?
C19 O4 Zn2 130.1(3) . . ?
C3 O6 Zn3 129.3(3) 16_554 . ?
O8 C7 O13 123.7(5) . . ?
O8 C7 C21 120.0(5) . . ?
O13 C7 C21 116.2(5) . . ?
C7 O8 Zn2 125.2(3) . . ?
C31 N9 C30 109.9(5) . . ?
C31 N9 C28 128.9(5) . . ?
C30 N9 C28 121.0(5) . . ?
C12 O10 Zn3 128.8(3) 16_554 . ?
O10 C12 O1 125.3(5) 16_554 . ?
O10 C12 C27 117.5(5) 16_554 . ?
O1 C12 C27 117.2(5) . . ?
C7 O13 Zn1 132.4(4) . . ?
C37 C14 C22 121.5(4) . . ?
C25 N15 C26 126.3(5) . . ?
C25 N15 C29 111.7(4) . . ?
C26 N15 C29 121.8(4) . . ?
C26 C16 C37 119.3(5) . . ?
C28 C17 C27 118.9(4) . . ?
C28 C18 C21 118.2(5) . . ?
O4 C19 O23 124.8(5) . 22_575 ?
O4 C19 C37 120.2(5) . 23_675 ?
O23 C19 C37 114.9(5) 22_575 23_675 ?
C26 C20 C22 119.5(5) . . ?
C18 C21 C24 119.3(4) . . ?
C18 C21 C7 120.2(5) . . ?
C24 C21 C7 120.5(5) . . ?
C20 C22 C14 118.6(4) . . ?
C20 C22 C3 121.0(4) . . ?
C14 C22 C3 120.2(4) . . ?
C19 O23 Zn1 127.3(4) 22_575 . ?
C27 C24 C21 120.0(5) . . ?
N15 C25 N15 107.9(6) 22_565 . ?
C20 C26 C16 122.0(5) . . ?
C20 C26 N15 120.0(5) . . ?
C16 C26 N15 117.9(4) . . ?
C24 C27 C17 120.8(5) . . ?
C24 C27 C12 119.5(5) . . ?
C17 C27 C12 119.6(5) . . ?
C17 C28 C18 122.7(5) . . ?
C17 C28 N9 119.3(4) . . ?
C18 C28 N9 118.0(5) . . ?
C29 C29 N15 104.3(3) 22_565 . ?
N9 C30 C30 103.2(4) . 21 ?
N9 C31 N9 113.8(7) . 21 ?
C14 C37 C16 119.0(5) . . ?
C14 C37 C19 119.7(5) . 31_665 ?
C16 C37 C19 121.3(5) . 31_665 ?
C12 O1 Zn3 123.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.085
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.028 0.135 0.010 22282.1 5788.5
_platon_squeeze_details          
; ?
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1Cu
_database_code_depnum_ccdc_archive 'CCDC 1037354'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 Cu2 N2 O10'
_chemical_formula_sum            'C19 H9 Cu2 N2 O10'
_chemical_formula_weight         552.36

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           Tetragonal
_symmetry_space_group_name_H-M   P42/nnm

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

_cell_length_a                   17.7179(7)
_cell_length_b                   17.7179(7)
_cell_length_c                   27.5566(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8650.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2200
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8232
_exptl_absorpt_correction_T_max  0.8232
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            73863
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3999
_reflns_number_gt                2876
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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)+(0.1169P)²+3.9238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3999
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2355
_refine_ls_wR_factor_gt          0.2123
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.03972(3) 0.53972(3) 0.53215(3) 0.0950(4) Uani 1 2 d S . .
Cu2 Cu 0.2500 0.32483(5) 0.7500 0.0901(4) Uani 1 2 d S . .
C2 C 0.1542(3) 0.2476(3) 0.68498(19) 0.0878(15) Uani 1 1 d . . .
C5 C 0.0368(3) 0.3139(3) 0.5773(2) 0.0969(16) Uani 1 1 d . . .
C4 C 0.0853(3) 0.3128(3) 0.61668(18) 0.0887(15) Uani 1 1 d . . .
H4 H 0.1104 0.3581 0.6257 0.106 Uiso 1 1 calc R . .
C3 C 0.0986(3) 0.2473(3) 0.6436(2) 0.0948(16) Uani 1 1 d . . .
C7 C 0.0109(3) 0.1821(3) 0.5926(2) 0.1022(18) Uani 1 1 d . . .
C6 C 0.0004(4) 0.2441(4) 0.5661(2) 0.119(2) Uani 1 1 d . . .
H6 H -0.0324 0.2418 0.5389 0.143 Uiso 1 1 calc R . .
C8 C 0.0580(3) 0.1811(3) 0.6307(2) 0.1059(17) Uani 1 1 d . . .
H8 H 0.0643 0.1361 0.6490 0.127 Uiso 1 1 calc R . .
O1 O 0.1822(2) 0.3106(2) 0.69464(12) 0.0998(11) Uani 1 1 d . . .
O2 O 0.1648(2) 0.1862(2) 0.70539(13) 0.0965(10) Uani 1 1 d . . .
N6 N -0.0302(3) 0.1165(3) 0.5807(2) 0.132(2) Uani 1 1 d . . .
C1 C 0.0245(3) 0.3840(3) 0.5476(2) 0.0930(15) Uani 1 1 d . . .
O3 O 0.0539(2) 0.44193(19) 0.56428(12) 0.0975(11) Uani 1 1 d . . .
O4 O -0.0149(2) 0.3756(2) 0.51046(13) 0.1086(12) Uani 1 1 d . . .
C9 C -0.0876(4) 0.0876(4) 0.5993(3) 0.129(3) Uani 1 2 d S . .
H9 H -0.1093 0.1093 0.6276 0.154 Uiso 1 2 calc SR . .
C10 C -0.0329(6) 0.0942(7) 0.5312(6) 0.301(8) Uani 1 1 d . . .
H10 H -0.0040 0.1126 0.5047 0.361 Uiso 1 1 calc R . .
O5 O 0.2500 0.4463(4) 0.7500 0.166(3) Uani 1 2 d S . .
O6 O 0.1053(2) 0.6053(2) 0.5812(2) 0.168(3) Uani 1 2 d S . .


_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 O4 1.955(4) 9_566 ?
Cu1 O4 1.955(4) 8_556 ?
Cu1 O3 1.962(4) . ?
Cu1 O3 1.962(4) 16_565 ?
Cu1 O6 2.128(5) . ?
Cu1 Cu1 2.6648(14) 9_566 ?
Cu2 O2 1.956(4) 5_556 ?
Cu2 O2 1.956(4) 3 ?
Cu2 O1 1.958(3) . ?
Cu2 O1 1.958(3) 6_556 ?
Cu2 O5 2.153(6) . ?
Cu2 Cu2 2.6515(17) 3 ?
C2 O2 1.239(6) . ?
C2 O1 1.251(6) . ?
C2 C3 1.505(8) . ?
C5 C4 1.385(7) . ?
C5 C6 1.429(7) . ?
C5 C1 1.502(8) . ?
C4 C3 1.399(7) . ?
C3 C8 1.422(7) . ?
C7 C6 1.332(8) . ?
C7 C8 1.342(8) . ?
C7 N6 1.410(6) . ?
O2 Cu2 1.956(4) 3 ?
N6 C9 1.249(7) . ?
N6 C10 1.420(14) . ?
C1 O3 1.240(5) . ?
C1 O4 1.248(6) . ?
O4 Cu1 1.955(4) 9_566 ?
C9 N6 1.249(7) 15 ?
C10 C10 1.535(17) 15 ?

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
O4 Cu1 O4 89.1(3) 9_566 8_556 ?
O4 Cu1 O3 167.82(13) 9_566 . ?
O4 Cu1 O3 88.51(17) 8_556 . ?
O4 Cu1 O3 88.51(17) 9_566 16_565 ?
O4 Cu1 O3 167.82(13) 8_556 16_565 ?
O3 Cu1 O3 91.3(2) . 16_565 ?
O4 Cu1 O6 94.91(16) 9_566 . ?
O4 Cu1 O6 94.91(16) 8_556 . ?
O3 Cu1 O6 97.19(15) . . ?
O3 Cu1 O6 97.19(15) 16_565 . ?
O4 Cu1 Cu1 83.52(10) 9_566 9_566 ?
O4 Cu1 Cu1 83.52(10) 8_556 9_566 ?
O3 Cu1 Cu1 84.34(9) . 9_566 ?
O3 Cu1 Cu1 84.34(9) 16_565 9_566 ?
O6 Cu1 Cu1 177.8(2) . 9_566 ?
O2 Cu2 O2 168.6(2) 5_556 3 ?
O2 Cu2 O1 90.20(15) 5_556 . ?
O2 Cu2 O1 88.33(15) 3 . ?
O2 Cu2 O1 88.33(15) 5_556 6_556 ?
O2 Cu2 O1 90.20(15) 3 6_556 ?
O1 Cu2 O1 165.2(2) . 6_556 ?
O2 Cu2 O5 95.72(11) 5_556 . ?
O2 Cu2 O5 95.72(11) 3 . ?
O1 Cu2 O5 97.38(11) . . ?
O1 Cu2 O5 97.38(11) 6_556 . ?
O2 Cu2 Cu2 84.28(11) 5_556 3 ?
O2 Cu2 Cu2 84.28(11) 3 3 ?
O1 Cu2 Cu2 82.62(11) . 3 ?
O1 Cu2 Cu2 82.62(11) 6_556 3 ?
O5 Cu2 Cu2 180.000(1) . 3 ?
O2 C2 O1 128.8(5) . . ?
O2 C2 C3 116.1(5) . . ?
O1 C2 C3 115.1(5) . . ?
C4 C5 C6 116.0(6) . . ?
C4 C5 C1 121.9(4) . . ?
C6 C5 C1 122.1(5) . . ?
C5 C4 C3 122.2(5) . . ?
C4 C3 C8 117.8(5) . . ?
C4 C3 C2 120.6(4) . . ?
C8 C3 C2 121.6(5) . . ?
C6 C7 C8 121.8(5) . . ?
C6 C7 N6 118.7(6) . . ?
C8 C7 N6 119.5(6) . . ?
C7 C6 C5 122.2(6) . . ?
C7 C8 C3 120.0(6) . . ?
C2 O1 Cu2 121.6(4) . . ?
C2 O2 Cu2 119.3(3) . 3 ?
C9 N6 C7 131.5(6) . . ?
C9 N6 C10 104.6(6) . . ?
C7 N6 C10 118.0(6) . . ?
O3 C1 O4 129.6(5) . . ?
O3 C1 C5 114.9(4) . . ?
O4 C1 C5 115.5(4) . . ?
C1 O3 Cu1 120.7(3) . . ?
C1 O4 Cu1 121.8(3) . 9_566 ?
N6 C9 N6 119.9(9) 15 . ?
N6 C10 C10 102.8(4) . 15 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.059
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.042 0.286 0.062 5549.9 1103.1
_platon_squeeze_details          
; ?
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2Cu
_database_code_depnum_ccdc_archive 'CCDC 1037355'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H9 Cu2 N2 O10'
_chemical_formula_sum            'C19 H9 Cu2 N2 O10'
_chemical_formula_weight         552.36

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           Tetragonal
_symmetry_space_group_name_H-M   I41/amd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'x, -y, -z'
'-x, y+1/2, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'-x, y, z'
'x, -y-1/2, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   25.4117(14)
_cell_length_b                   25.4117(14)
_cell_length_c                   52.162(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     33684(5)
_cell_formula_units_Z            32
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             8800
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8112
_exptl_absorpt_correction_T_max  0.8349
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            192704
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_av_sigmaI/netI    0.0969
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -69
_diffrn_reflns_limit_l_max       69
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.38
_reflns_number_total             10995
_reflns_number_gt                6605
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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)+(0.0952P)²+3.8495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10995
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.223377(19) 0.451685(19) 0.126140(9) 0.02753(15) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.54479(3) 0.261831(12) 0.02733(19) Uani 1 2 d S . .
Cu3 Cu 0.0000 0.47153(3) 0.225360(12) 0.02739(19) Uani 1 2 d S . .
O2 O 0.20018(12) 0.49879(11) 0.15465(5) 0.0409(7) Uani 1 1 d . . .
O3 O 0.05403(11) 0.58012(10) 0.24114(5) 0.0359(7) Uani 1 1 d . . .
O4 O 0.05402(11) 0.51681(11) 0.21126(5) 0.0409(7) Uani 1 1 d . . .
O5 O 0.05347(13) 0.43708(11) 0.24605(6) 0.0493(9) Uani 1 1 d . . .
O6 O 0.05413(12) 0.49874(11) 0.27633(5) 0.0393(7) Uani 1 1 d . . .
C2 C 0.21653(16) 0.54418(16) 0.15877(8) 0.0328(10) Uani 1 1 d . . .
C6 C 0.16658(16) 0.41510(15) 0.31700(8) 0.0339(10) Uani 1 1 d . . .
C7 C 0.18853(16) 0.57593(15) 0.17816(8) 0.0322(10) Uani 1 1 d . . .
C8 C 0.14349(16) 0.55620(15) 0.18993(8) 0.0348(10) Uani 1 1 d . . .
H8 H 0.1308 0.5226 0.1849 0.042 Uiso 1 1 calc R . .
C9 C 0.11711(16) 0.58301(15) 0.20826(8) 0.0331(10) Uani 1 1 d . . .
C10 C 0.07128(17) 0.55852(16) 0.22131(8) 0.0361(10) Uani 1 1 d . . .
O11 O 0.0000 0.4128(2) 0.19599(10) 0.0837(17) Uani 1 2 d S . .
C12 C 0.06913(18) 0.45581(17) 0.26663(8) 0.0370(10) Uani 1 1 d . . .
C13 C 0.10810(16) 0.42441(15) 0.28153(7) 0.0310(9) Uani 1 1 d . . .
C14 C 0.12057(17) 0.37507(16) 0.27385(8) 0.0374(10) Uani 1 1 d . . .
H14 H 0.1046 0.3602 0.2591 0.045 Uiso 1 1 calc R . .
C15 C 0.15722(17) 0.34639(15) 0.28806(8) 0.0378(11) Uani 1 1 d . . .
C16 C 0.17941(17) 0.36608(15) 0.30939(8) 0.0353(10) Uani 1 1 d . . .
H16 H 0.2038 0.3457 0.3190 0.042 Uiso 1 1 calc R . .
C17 C 0.13054(16) 0.44431(15) 0.30337(7) 0.0319(10) Uani 1 1 d . . .
H17 H 0.1211 0.4785 0.3091 0.038 Uiso 1 1 calc R . .
N18 N 0.16684(15) 0.29248(13) 0.28025(7) 0.0455(10) Uani 1 1 d . . .
C19 C 0.1808(2) 0.27626(17) 0.25538(9) 0.0550(14) Uani 1 1 d . . .
H19 H 0.1887 0.2985 0.2413 0.066 Uiso 1 1 calc R . .
C20 C 0.1560(3) 0.2500 0.29551(12) 0.0426(16) Uani 1 2 d S . .
H20 H 0.1438 0.2500 0.3127 0.051 Uiso 1 2 calc SR . .
O21 O 0.0000 0.6025(2) 0.29284(10) 0.0852(17) Uani 1 2 d S . .
C22 C 0.13381(15) 0.63391(15) 0.21470(8) 0.0324(10) Uani 1 1 d . . .
H22 H 0.1161 0.6538 0.2275 0.039 Uiso 1 1 calc R . .
C23 C 0.17648(17) 0.65415(15) 0.20197(8) 0.0375(10) Uani 1 1 d . . .
C24 C 0.20424(17) 0.62647(15) 0.18410(8) 0.0348(10) Uani 1 1 d . . .
H24 H 0.2339 0.6417 0.1759 0.042 Uiso 1 1 calc R . .
N25 N 0.19322(13) 0.70835(12) 0.20725(7) 0.0368(9) Uani 1 1 d . . .
C26 C 0.24211(19) 0.72347(16) 0.21478(9) 0.0513(13) Uani 1 1 d . . .
H26 H 0.2707 0.7011 0.2192 0.062 Uiso 1 1 calc R . .
C27 C 0.1649(3) 0.7500 0.20184(12) 0.0454(17) Uani 1 2 d S . .
H27 H 0.1301 0.7500 0.1952 0.054 Uiso 1 2 calc SR . .
C5 C 0.19313(18) 0.44037(16) 0.33990(7) 0.0348(10) Uani 1 1 d . . .
O1 O 0.23126(11) 0.41611(10) 0.34956(5) 0.0376(7) Uani 1 1 d . . .
O8 O 0.17518(12) 0.48385(11) 0.34728(5) 0.0394(7) Uani 1 1 d . . .
O7 O 0.25538(12) 0.56588(10) 0.14783(5) 0.0398(7) Uani 1 1 d . . .
O9 O 0.16255(16) 0.39402(16) 0.12823(7) 0.0859(13) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O7 1.936(3) 16_554 ?
Cu1 O1 1.937(3) 14_545 ?
Cu1 O8 1.975(3) 10_544 ?
Cu1 O2 1.998(3) . ?
Cu1 O9 2.133(4) . ?
Cu1 Cu1 2.6957(9) 16_554 ?
Cu2 O6 1.958(3) . ?
Cu2 O6 1.958(3) 21 ?
Cu2 O3 1.964(3) 21 ?
Cu2 O3 1.964(3) . ?
Cu2 O21 2.184(6) . ?
Cu2 Cu3 2.6617(9) . ?
Cu3 O4 1.936(3) 21 ?
Cu3 O4 1.936(3) . ?
Cu3 O5 1.944(3) . ?
Cu3 O5 1.944(3) 21 ?
Cu3 O11 2.139(5) . ?
O2 C2 1.245(5) . ?
O3 C10 1.250(5) . ?
O4 C10 1.261(5) . ?
O5 C12 1.240(5) . ?
O6 C12 1.262(5) . ?
C2 O7 1.267(5) . ?
C2 C7 1.477(5) . ?
C6 C16 1.347(5) . ?
C6 C17 1.377(5) . ?
C6 C5 1.514(5) . ?
C7 C24 1.380(5) . ?
C7 C8 1.392(5) . ?
C8 C9 1.352(5) . ?
C8 H8 0.9500 . ?
C9 C22 1.402(5) . ?
C9 C10 1.485(6) . ?
C12 C13 1.490(6) . ?
C13 C14 1.354(5) . ?
C13 C17 1.371(5) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.344(5) . ?
C15 N18 1.450(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N18 C20 1.369(5) . ?
N18 C19 1.406(5) . ?
C19 C19 1.334(8) 22_565 ?
C19 H19 0.9500 . ?
C20 N18 1.369(5) 22_565 ?
C20 H20 0.9500 . ?
C22 C23 1.372(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.364(5) . ?
C23 N25 1.468(5) . ?
C24 H24 0.9500 . ?
N25 C27 1.311(5) . ?
N25 C26 1.358(5) . ?
C26 C26 1.348(8) 22_575 ?
C26 H26 0.9500 . ?
C27 N25 1.311(5) 22_575 ?
C27 H27 0.9500 . ?
C5 O1 1.254(5) . ?
C5 O8 1.256(5) . ?
O1 Cu1 1.937(3) 14_545 ?
O8 Cu1 1.975(3) 12_454 ?
O7 Cu1 1.936(3) 16_554 ?

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
O7 Cu1 O1 172.79(12) 16_554 14_545 ?
O7 Cu1 O8 89.06(12) 16_554 10_544 ?
O1 Cu1 O8 90.69(12) 14_545 10_544 ?
O7 Cu1 O2 89.48(13) 16_554 . ?
O1 Cu1 O2 88.18(12) 14_545 . ?
O8 Cu1 O2 159.06(12) 10_544 . ?
O7 Cu1 O9 92.68(14) 16_554 . ?
O1 Cu1 O9 94.43(13) 14_545 . ?
O8 Cu1 O9 101.73(14) 10_544 . ?
O2 Cu1 O9 99.20(14) . . ?
O7 Cu1 Cu1 86.41(9) 16_554 16_554 ?
O1 Cu1 Cu1 86.46(8) 14_545 16_554 ?
O8 Cu1 Cu1 79.55(9) 10_544 16_554 ?
O2 Cu1 Cu1 79.51(9) . 16_554 ?
O9 Cu1 Cu1 178.42(12) . 16_554 ?
O6 Cu2 O6 89.26(18) . 21 ?
O6 Cu2 O3 167.63(12) . 21 ?
O6 Cu2 O3 89.68(12) 21 21 ?
O6 Cu2 O3 89.68(12) . . ?
O6 Cu2 O3 167.63(12) 21 . ?
O3 Cu2 O3 88.73(16) 21 . ?
O6 Cu2 O21 96.63(13) . . ?
O6 Cu2 O21 96.63(13) 21 . ?
O3 Cu2 O21 95.73(13) 21 . ?
O3 Cu2 O21 95.73(13) . . ?
O6 Cu2 Cu3 81.84(8) . . ?
O6 Cu2 Cu3 81.84(8) 21 . ?
O3 Cu2 Cu3 85.81(8) 21 . ?
O3 Cu2 Cu3 85.81(8) . . ?
O21 Cu2 Cu3 177.83(15) . . ?
O4 Cu3 O4 90.29(18) 21 . ?
O4 Cu3 O5 166.96(13) 21 . ?
O4 Cu3 O5 89.03(13) . . ?
O4 Cu3 O5 89.03(13) 21 21 ?
O4 Cu3 O5 166.96(13) . 21 ?
O5 Cu3 O5 88.7(2) . 21 ?
O4 Cu3 O11 98.21(13) 21 . ?
O4 Cu3 O11 98.21(13) . . ?
O5 Cu3 O11 94.78(14) . . ?
O5 Cu3 O11 94.78(14) 21 . ?
O4 Cu3 Cu2 81.71(8) 21 . ?
O4 Cu3 Cu2 81.71(8) . . ?
O5 Cu3 Cu2 85.30(9) . . ?
O5 Cu3 Cu2 85.30(9) 21 . ?
O11 Cu3 Cu2 179.89(15) . . ?
C2 O2 Cu1 125.8(3) . . ?
C10 O3 Cu2 119.9(3) . . ?
C10 O4 Cu3 126.0(3) . . ?
C12 O5 Cu3 122.2(3) . . ?
C12 O6 Cu2 125.0(3) . . ?
O2 C2 O7 125.8(4) . . ?
O2 C2 C7 117.6(4) . . ?
O7 C2 C7 116.5(4) . . ?
C16 C6 C17 120.5(4) . . ?
C16 C6 C5 121.1(4) . . ?
C17 C6 C5 118.3(4) . . ?
C24 C7 C8 118.3(4) . . ?
C24 C7 C2 121.5(4) . . ?
C8 C7 C2 120.1(4) . . ?
C9 C8 C7 122.5(4) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C22 119.0(4) . . ?
C8 C9 C10 120.1(4) . . ?
C22 C9 C10 120.9(4) . . ?
O3 C10 O4 126.2(4) . . ?
O3 C10 C9 118.0(4) . . ?
O4 C10 C9 115.7(4) . . ?
O5 C12 O6 125.6(4) . . ?
O5 C12 C13 117.3(4) . . ?
O6 C12 C13 117.0(4) . . ?
C14 C13 C17 119.4(4) . . ?
C14 C13 C12 119.8(4) . . ?
C17 C13 C12 120.8(4) . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 N18 120.9(4) . . ?
C14 C15 N18 117.2(4) . . ?
C15 C16 C6 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C6 C16 H16 120.4 . . ?
C13 C17 C6 120.5(4) . . ?
C13 C17 H17 119.8 . . ?
C6 C17 H17 119.8 . . ?
C20 N18 C19 110.8(4) . . ?
C20 N18 C15 123.2(4) . . ?
C19 N18 C15 125.4(4) . . ?
C19 C19 N18 107.1(2) 22_565 . ?
C19 C19 H19 126.5 22_565 . ?
N18 C19 H19 126.5 . . ?
N18 C20 N18 104.1(5) 22_565 . ?
N18 C20 H20 128.0 22_565 . ?
N18 C20 H20 128.0 . . ?
C23 C22 C9 118.0(4) . . ?
C23 C22 H22 121.0 . . ?
C9 C22 H22 121.0 . . ?
C24 C23 C22 123.1(4) . . ?
C24 C23 N25 117.5(4) . . ?
C22 C23 N25 119.4(4) . . ?
C23 C24 C7 118.9(4) . . ?
C23 C24 H24 120.5 . . ?
C7 C24 H24 120.5 . . ?
C27 N25 C26 109.6(4) . . ?
C27 N25 C23 123.9(4) . . ?
C26 N25 C23 125.8(3) . . ?
C26 C26 N25 106.4(2) 22_575 . ?
C26 C26 H26 126.8 22_575 . ?
N25 C26 H26 126.8 . . ?
N25 C27 N25 107.7(6) . 22_575 ?
N25 C27 H27 126.1 . . ?
N25 C27 H27 126.1 22_575 . ?
O1 C5 O8 126.1(4) . . ?
O1 C5 C6 116.9(4) . . ?
O8 C5 C6 117.0(4) . . ?
C5 O1 Cu1 119.6(3) . 14_545 ?
C5 O8 Cu1 126.4(3) . 12_454 ?
C2 O7 Cu1 120.4(3) . 16_554 ?

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
O6 Cu2 Cu3 O4 179.46(13) . . . 21 ?
O6 Cu2 Cu3 O4 89.03(13) 21 . . 21 ?
O3 Cu2 Cu3 O4 -1.24(12) 21 . . 21 ?
O3 Cu2 Cu3 O4 -90.27(12) . . . 21 ?
O21 Cu2 Cu3 O4 134.25(9) . . . 21 ?
O6 Cu2 Cu3 O4 -89.03(13) . . . . ?
O6 Cu2 Cu3 O4 -179.46(13) 21 . . . ?
O3 Cu2 Cu3 O4 90.27(12) 21 . . . ?
O3 Cu2 Cu3 O4 1.24(12) . . . . ?
O21 Cu2 Cu3 O4 -134.25(9) . . . . ?
O6 Cu2 Cu3 O5 0.66(13) . . . . ?
O6 Cu2 Cu3 O5 -89.76(14) 21 . . . ?
O3 Cu2 Cu3 O5 179.97(13) 21 . . . ?
O3 Cu2 Cu3 O5 90.94(13) . . . . ?
O21 Cu2 Cu3 O5 -44.55(10) . . . . ?
O6 Cu2 Cu3 O5 89.76(14) . . . 21 ?
O6 Cu2 Cu3 O5 -0.67(13) 21 . . 21 ?
O3 Cu2 Cu3 O5 -90.94(13) 21 . . 21 ?
O3 Cu2 Cu3 O5 -179.97(13) . . . 21 ?
O21 Cu2 Cu3 O5 44.55(10) . . . 21 ?
O6 Cu2 Cu3 O11 -135(100) . . . . ?
O6 Cu2 Cu3 O11 135(100) 21 . . . ?
O3 Cu2 Cu3 O11 45(100) 21 . . . ?
O3 Cu2 Cu3 O11 -45(100) . . . . ?
O21 Cu2 Cu3 O11 180(100) . . . . ?
O7 Cu1 O2 C2 -73.3(4) 16_554 . . . ?
O1 Cu1 O2 C2 99.9(3) 14_545 . . . ?
O8 Cu1 O2 C2 12.7(6) 10_544 . . . ?
O9 Cu1 O2 C2 -165.9(3) . . . . ?
Cu1 Cu1 O2 C2 13.2(3) 16_554 . . . ?
O6 Cu2 O3 C10 77.6(3) . . . . ?
O6 Cu2 O3 C10 -7.5(8) 21 . . . ?
O3 Cu2 O3 C10 -90.1(3) 21 . . . ?
O21 Cu2 O3 C10 174.2(3) . . . . ?
Cu3 Cu2 O3 C10 -4.3(3) . . . . ?
O4 Cu3 O4 C10 83.1(4) 21 . . . ?
O5 Cu3 O4 C10 -83.9(3) . . . . ?
O5 Cu3 O4 C10 -3.9(8) 21 . . . ?
O11 Cu3 O4 C10 -178.6(3) . . . . ?
Cu2 Cu3 O4 C10 1.5(3) . . . . ?
O4 Cu3 O5 C12 -5.1(8) 21 . . . ?
O4 Cu3 O5 C12 82.0(3) . . . . ?
O5 Cu3 O5 C12 -85.2(4) 21 . . . ?
O11 Cu3 O5 C12 -179.8(3) . . . . ?
Cu2 Cu3 O5 C12 0.2(3) . . . . ?
O6 Cu2 O6 C12 80.0(4) 21 . . . ?
O3 Cu2 O6 C12 -5.1(8) 21 . . . ?
O3 Cu2 O6 C12 -87.7(3) . . . . ?
O21 Cu2 O6 C12 176.6(3) . . . . ?
Cu3 Cu2 O6 C12 -1.9(3) . . . . ?
Cu1 O2 C2 O7 -9.9(6) . . . . ?
Cu1 O2 C2 C7 170.2(3) . . . . ?
O2 C2 C7 C24 179.5(4) . . . . ?
O7 C2 C7 C24 -0.4(6) . . . . ?
O2 C2 C7 C8 -4.1(6) . . . . ?
O7 C2 C7 C8 176.1(4) . . . . ?
C24 C7 C8 C9 -5.2(6) . . . . ?
C2 C7 C8 C9 178.3(4) . . . . ?
C7 C8 C9 C22 3.8(6) . . . . ?
C7 C8 C9 C10 -176.1(4) . . . . ?
Cu2 O3 C10 O4 7.0(6) . . . . ?
Cu2 O3 C10 C9 -171.7(3) . . . . ?
Cu3 O4 C10 O3 -5.6(6) . . . . ?
Cu3 O4 C10 C9 173.1(3) . . . . ?
C8 C9 C10 O3 167.1(4) . . . . ?
C22 C9 C10 O3 -12.7(6) . . . . ?
C8 C9 C10 O4 -11.7(6) . . . . ?
C22 C9 C10 O4 168.4(4) . . . . ?
Cu3 O5 C12 O6 -1.8(6) . . . . ?
Cu3 O5 C12 C13 176.7(3) . . . . ?
Cu2 O6 C12 O5 2.8(6) . . . . ?
Cu2 O6 C12 C13 -175.7(3) . . . . ?
O5 C12 C13 C14 -7.2(6) . . . . ?
O6 C12 C13 C14 171.4(4) . . . . ?
O5 C12 C13 C17 174.6(4) . . . . ?
O6 C12 C13 C17 -6.8(6) . . . . ?
C17 C13 C14 C15 -1.9(6) . . . . ?
C12 C13 C14 C15 179.9(4) . . . . ?
C13 C14 C15 C16 1.5(7) . . . . ?
C13 C14 C15 N18 175.9(4) . . . . ?
C14 C15 C16 C6 -1.1(7) . . . . ?
N18 C15 C16 C6 -175.3(4) . . . . ?
C17 C6 C16 C15 1.1(6) . . . . ?
C5 C6 C16 C15 -176.0(4) . . . . ?
C14 C13 C17 C6 1.9(6) . . . . ?
C12 C13 C17 C6 -179.9(4) . . . . ?
C16 C6 C17 C13 -1.5(6) . . . . ?
C5 C6 C17 C13 175.6(4) . . . . ?
C16 C15 N18 C20 57.6(7) . . . . ?
C14 C15 N18 C20 -116.9(5) . . . . ?
C16 C15 N18 C19 -132.2(5) . . . . ?
C14 C15 N18 C19 53.4(6) . . . . ?
C20 N18 C19 C19 -2.5(4) . . . 22_565 ?
C15 N18 C19 C19 -173.8(3) . . . 22_565 ?
C19 N18 C20 N18 3.9(7) . . . 22_565 ?
C15 N18 C20 N18 175.4(3) . . . 22_565 ?
C8 C9 C22 C23 0.0(6) . . . . ?
C10 C9 C22 C23 179.8(4) . . . . ?
C9 C22 C23 C24 -2.3(6) . . . . ?
C9 C22 C23 N25 176.7(4) . . . . ?
C22 C23 C24 C7 0.9(7) . . . . ?
N25 C23 C24 C7 -178.1(4) . . . . ?
C8 C7 C24 C23 2.7(6) . . . . ?
C2 C7 C24 C23 179.2(4) . . . . ?
C24 C23 N25 C27 113.6(5) . . . . ?
C22 C23 N25 C27 -65.5(6) . . . . ?
C24 C23 N25 C26 -56.2(6) . . . . ?
C22 C23 N25 C26 124.7(5) . . . . ?
C27 N25 C26 C26 2.4(4) . . . 22_575 ?
C23 N25 C26 C26 173.5(3) . . . 22_575 ?
C26 N25 C27 N25 -4.0(7) . . . 22_575 ?
C23 N25 C27 N25 -175.2(3) . . . 22_575 ?
C16 C6 C5 O1 7.7(6) . . . . ?
C17 C6 C5 O1 -169.5(4) . . . . ?
C16 C6 C5 O8 -172.9(4) . . . . ?
C17 C6 C5 O8 9.9(6) . . . . ?
O8 C5 O1 Cu1 -12.4(6) . . . 14_545 ?
C6 C5 O1 Cu1 166.9(3) . . . 14_545 ?
O1 C5 O8 Cu1 0.1(6) . . . 12_454 ?
C6 C5 O8 Cu1 -179.3(3) . . . 12_454 ?
O2 C2 O7 Cu1 -4.3(6) . . . 16_554 ?
C7 C2 O7 Cu1 175.6(3) . . . 16_554 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.538
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.105

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.022 0.149 0.002 21294.1 5739.2
_platon_squeeze_details          
; ?
;


