# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 1423819'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_audit_creation_date             2014-10-29
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H20 Cu N6 O8'
_chemical_formula_sum            'C18 H20 Cu N6 O8'
_chemical_formula_weight         511.94
_chemical_melting_point          ?
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.2530(15)
_cell_length_b                   7.052(2)
_cell_length_c                   12.075(3)
_cell_angle_alpha                79.90(2)
_cell_angle_beta                 88.21(2)
_cell_angle_gamma                71.13(2)
_cell_volume                     495.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9910
_cell_measurement_theta_min      3.4070
_exptl_absorpt_coefficient_mu    1.165
_exptl_absorpt_correction_T_max  0.8728
_exptl_absorpt_correction_T_min  0.8539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            bluish
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             263
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.1108
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3061
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1416
_reflns_number_total             1923
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1842
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.5000 0.5000 0.0000 0.0340(4) Uani 1 2 d S . .
O1 O 0.7719(6) 0.2413(7) 0.0188(3) 0.0404(11) Uani 1 1 d . . .
H1A H 0.7370 0.1254 0.0297 0.061 Uiso 1 1 d R . .
H1B H 0.8572 0.2356 0.0765 0.061 Uiso 1 1 d R . .
O2 O 0.6571(6) 0.0207(7) 0.8721(3) 0.0409(11) Uani 1 1 d . . .
O3 O 0.7154(6) 0.6905(7) 0.0575(3) 0.0421(11) Uani 1 1 d . . .
H3A H 0.6429 0.7770 0.1056 0.063 Uiso 1 1 d R . .
H3B H 0.7500 0.7744 -0.0029 0.063 Uiso 1 1 d R . .
O4 O 0.9936(7) -0.0637(8) 0.7950(3) 0.0498(13) Uani 1 1 d . . .
N5 N 0.4268(7) 0.3583(7) 0.3422(4) 0.0279(11) Uani 1 1 d . . .
N1 N 0.1994(7) 0.4338(8) 0.3141(4) 0.0363(12) Uani 1 1 d . . .
N2 N 0.4102(7) 0.4473(7) 0.1604(4) 0.0315(11) Uani 1 1 d . . .
C3 C 0.5077(9) 0.2812(9) 0.4552(4) 0.0302(13) Uani 1 1 d . . .
C1 C 0.8181(9) 0.1489(10) 0.5867(4) 0.0347(14) Uani 1 1 d . . .
H1 H 0.9721 0.1143 0.6022 0.042 Uiso 1 1 calc R . .
C2 C 0.6765(9) 0.1136(8) 0.6733(4) 0.0275(12) Uani 1 1 d . . .
C4 C 0.5454(10) 0.3685(9) 0.2489(4) 0.0340(14) Uani 1 1 d . . .
H4 H 0.7024 0.3256 0.2470 0.041 Uiso 1 1 calc R . .
C6 C 0.7362(9) 0.2335(10) 0.4794(5) 0.0370(15) Uani 1 1 d . . .
H6 H 0.8331 0.2588 0.4230 0.044 Uiso 1 1 calc R . .
C7 C 0.3622(9) 0.2526(9) 0.5403(4) 0.0361(15) Uani 1 1 d . . .
H7 H 0.2081 0.2885 0.5248 0.043 Uiso 1 1 calc R . .
C8 C 0.7826(10) 0.0153(9) 0.7887(5) 0.0341(14) Uani 1 1 d . . .
C9 C 0.4482(9) 0.1697(10) 0.6492(5) 0.0335(14) Uani 1 1 d . . .
H9 H 0.3503 0.1519 0.7067 0.040 Uiso 1 1 calc R . .
C10 C 0.1995(9) 0.4845(9) 0.2038(5) 0.0357(14) Uani 1 1 d . . .
H10 H 0.0677 0.5407 0.1594 0.043 Uiso 1 1 calc R . .

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 0.0267(6) 0.0361(7) 0.0291(6) 0.0001(4) -0.0052(4) 0.0010(4)
O1 0.040(2) 0.039(3) 0.033(2) -0.0013(19) -0.0076(18) -0.002(2)
O2 0.036(2) 0.047(3) 0.031(2) -0.0035(19) -0.0013(18) -0.003(2)
O3 0.034(2) 0.048(3) 0.040(2) -0.002(2) 0.0032(19) -0.010(2)
O4 0.030(2) 0.067(4) 0.035(2) -0.002(2) -0.0081(18) 0.004(2)
N5 0.020(2) 0.028(3) 0.029(2) -0.002(2) -0.0015(18) -0.001(2)
N1 0.021(2) 0.047(4) 0.036(3) -0.002(2) -0.004(2) -0.007(2)
N2 0.024(2) 0.031(3) 0.033(3) -0.006(2) -0.004(2) 0.000(2)
C3 0.028(3) 0.032(4) 0.025(3) -0.004(2) -0.002(2) -0.004(2)
C1 0.021(3) 0.048(4) 0.032(3) -0.005(3) -0.001(2) -0.007(3)
C2 0.027(3) 0.021(3) 0.029(3) -0.003(2) -0.001(2) -0.001(2)
C4 0.031(3) 0.036(4) 0.030(3) 0.000(3) -0.004(2) -0.006(3)
C6 0.028(3) 0.046(4) 0.033(3) -0.004(3) 0.001(2) -0.007(3)
C7 0.026(3) 0.043(4) 0.034(3) -0.005(3) -0.003(2) -0.005(3)
C8 0.038(3) 0.029(4) 0.031(3) -0.007(3) -0.004(3) -0.004(3)
C9 0.027(3) 0.042(4) 0.029(3) -0.002(3) 0.005(2) -0.010(3)
C10 0.026(3) 0.036(4) 0.040(3) -0.003(3) -0.006(2) -0.004(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 2.035(4) 2_665 ?
Cu1 O1 2.035(4) . ?
Cu1 O3 2.378(4) 2_665 ?
Cu1 O3 2.378(4) . ?
Cu1 N2 2.005(4) . ?
Cu1 N2 2.005(4) 2_665 ?
O2 C8 1.256(6) . ?
O4 C8 1.254(7) . ?
N5 N1 1.378(6) . ?
N5 C3 1.421(7) . ?
N5 C4 1.334(6) . ?
N1 C10 1.318(7) . ?
N2 C4 1.307(7) . ?
N2 C10 1.364(6) . ?
C3 C6 1.386(8) . ?
C3 C7 1.383(7) . ?
C1 C2 1.390(7) . ?
C1 C6 1.368(8) . ?
C2 C8 1.511(8) . ?
C2 C9 1.378(7) . ?
C7 C9 1.389(8) . ?

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 180.0(3) . 2_665 ?
O1 Cu1 O3 92.16(16) 2_665 2_665 ?
O1 Cu1 O3 87.84(16) . 2_665 ?
O1 Cu1 O3 87.84(16) 2_665 . ?
O1 Cu1 O3 92.16(16) . . ?
O3 Cu1 O3 180.00(17) 2_665 . ?
N2 Cu1 O1 93.47(16) 2_665 2_665 ?
N2 Cu1 O1 93.47(16) . . ?
N2 Cu1 O1 86.53(16) 2_665 . ?
N2 Cu1 O1 86.53(16) . 2_665 ?
N2 Cu1 O3 88.04(16) 2_665 2_665 ?
N2 Cu1 O3 88.04(16) . . ?
N2 Cu1 O3 91.96(16) 2_665 . ?
N2 Cu1 O3 91.96(16) . 2_665 ?
N2 Cu1 N2 180.0(2) 2_665 . ?
N1 N5 C3 122.1(4) . . ?
C4 N5 N1 109.3(4) . . ?
C4 N5 C3 128.6(5) . . ?
C10 N1 N5 102.4(4) . . ?
C4 N2 Cu1 126.9(4) . . ?
C4 N2 C10 103.8(5) . . ?
C10 N2 Cu1 129.3(4) . . ?
C6 C3 N5 119.0(5) . . ?
C7 C3 N5 120.9(5) . . ?
C7 C3 C6 120.1(5) . . ?
C6 C1 C2 121.5(5) . . ?
C1 C2 C8 117.9(5) . . ?
C9 C2 C1 118.4(5) . . ?
C9 C2 C8 123.8(5) . . ?
N2 C4 N5 110.5(5) . . ?
C1 C6 C3 119.5(5) . . ?
C3 C7 C9 119.4(5) . . ?
O2 C8 C2 118.8(5) . . ?
O4 C8 O2 124.0(5) . . ?
O4 C8 C2 117.2(5) . . ?
C2 C9 C7 121.0(5) . . ?
N1 C10 N2 114.0(5) . . ?
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1423820'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_audit_creation_date             2014-10-29
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C36 H24 Cu2 N12 O8)'
_chemical_formula_sum            'C18 H12 Cu N6 O4'
_chemical_formula_weight         439.88
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z'
3 'x, -y+1/2, -z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z'
7 '-x, y-1/2, z-1/2'
8 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0574(5)
_cell_length_b                   9.9328(4)
_cell_length_c                   17.5051(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2270.36(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1699
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.8829
_cell_measurement_theta_min      2.5712
_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_T_max  0.8260
_exptl_absorpt_correction_T_min  0.7964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5397
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.83
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1577
_reflns_number_total             2244
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1292
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.7500 0.0000 0.66204(3) 0.0314(2) Uani 1 2 d S . .
O1 O 0.65010(16) 0.0520(2) 0.58227(11) 0.0421(5) Uani 1 1 d . . .
N3 N 0.3612(2) 0.5046(2) 0.23988(15) 0.0419(7) Uani 1 1 d . . .
N1 N 0.4632(2) 0.4522(3) 0.33307(15) 0.0503(8) Uani 1 1 d . . .
O2 O 0.72560(18) 0.2398(2) 0.61854(13) 0.0526(6) Uani 1 1 d . . .
C8 C 0.3735(2) 0.4281(3) 0.30088(17) 0.0392(7) Uani 1 1 d . . .
H8 H 0.3258 0.3660 0.3187 0.047 Uiso 1 1 calc R . .
C1 C 0.6658(2) 0.1778(3) 0.57577(16) 0.0378(7) Uani 1 1 d . . .
C2 C 0.6085(2) 0.2521(3) 0.51423(17) 0.0405(7) Uani 1 1 d . . .
C5 C 0.5120(3) 0.3850(3) 0.39616(18) 0.0443(8) Uani 1 1 d . . .
C4 C 0.4761(3) 0.2633(3) 0.4198(2) 0.0611(11) Uani 1 1 d . . .
H4 H 0.4194 0.2250 0.3962 0.073 Uiso 1 1 calc R . .
C3 C 0.5246(3) 0.1968(4) 0.4794(2) 0.0587(10) Uani 1 1 d . . .
H3 H 0.4999 0.1139 0.4958 0.070 Uiso 1 1 calc R . .
C7 C 0.6419(3) 0.3758(3) 0.4901(2) 0.0690(12) Uani 1 1 d . . .
H7 H 0.6978 0.4154 0.5142 0.083 Uiso 1 1 calc R . .
C6 C 0.5947(3) 0.4430(4) 0.4308(2) 0.0745(14) Uani 1 1 d . . .
H6 H 0.6187 0.5264 0.4147 0.089 Uiso 1 1 calc R . .
N2 N 0.5131(3) 0.5490(4) 0.2928(2) 0.1059(17) Uani 1 1 d . . .
C9 C 0.4490(3) 0.5765(5) 0.2379(3) 0.0955(18) Uani 1 1 d . . .
H9 H 0.4625 0.6404 0.2004 0.115 Uiso 1 1 calc R . .

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 0.0324(3) 0.0390(3) 0.0229(3) 0.000 0.000 -0.0028(2)
O1 0.0474(13) 0.0440(11) 0.0349(11) 0.0081(10) -0.0115(11) -0.0103(11)
N3 0.0403(15) 0.0509(15) 0.0344(14) 0.0110(12) -0.0064(13) -0.0119(13)
N1 0.0492(18) 0.0550(15) 0.0469(17) 0.0245(13) -0.0181(15) -0.0219(16)
O2 0.0568(15) 0.0565(13) 0.0445(13) 0.0037(11) -0.0235(12) -0.0156(12)
C8 0.0363(17) 0.0508(18) 0.0305(15) 0.0100(14) -0.0038(15) -0.0113(16)
C1 0.0354(17) 0.0480(17) 0.0299(15) 0.0033(13) -0.0036(14) -0.0104(15)
C2 0.0421(18) 0.0432(16) 0.0361(16) 0.0046(14) -0.0100(15) -0.0125(15)
C5 0.0415(19) 0.0504(18) 0.0411(19) 0.0161(14) -0.0131(16) -0.0126(16)
C4 0.058(2) 0.056(2) 0.069(2) 0.0238(19) -0.034(2) -0.0284(18)
C3 0.059(2) 0.0503(19) 0.067(2) 0.0241(18) -0.027(2) -0.0254(18)
C7 0.070(3) 0.062(2) 0.075(2) 0.0264(19) -0.046(2) -0.036(2)
C6 0.083(3) 0.058(2) 0.083(3) 0.038(2) -0.045(3) -0.042(2)
N2 0.085(3) 0.128(3) 0.105(3) 0.083(3) -0.056(3) -0.067(3)
C9 0.082(3) 0.116(4) 0.088(3) 0.072(3) -0.046(3) -0.059(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 1.979(2) 2_655 ?
Cu1 O1 1.979(2) . ?
Cu1 N3 1.991(3) 7_656 ?
Cu1 N3 1.991(3) 8_666 ?
O1 C1 1.271(4) . ?
N3 Cu1 1.991(3) 7_665 ?
N3 C8 1.321(4) . ?
N3 C9 1.351(4) . ?
N1 C8 1.321(4) . ?
N1 C5 1.440(4) . ?
N1 N2 1.358(4) . ?
O2 C1 1.245(3) . ?
C1 C2 1.505(4) . ?
C2 C3 1.369(4) . ?
C2 C7 1.371(4) . ?
C5 C4 1.361(4) . ?
C5 C6 1.365(4) . ?
C4 C3 1.387(4) . ?
C7 C6 1.379(5) . ?
N2 C9 1.304(5) . ?

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 90.26(13) . 2_655 ?
O1 Cu1 N3 89.79(10) . 7_656 ?
O1 Cu1 N3 165.71(9) 2_655 7_656 ?
O1 Cu1 N3 89.79(10) 2_655 8_666 ?
O1 Cu1 N3 165.71(9) . 8_666 ?
N3 Cu1 N3 93.65(16) 8_666 7_656 ?
C1 O1 Cu1 102.31(18) . . ?
C8 N3 Cu1 129.0(2) . 7_665 ?
C8 N3 C9 102.8(3) . . ?
C9 N3 Cu1 127.8(2) . 7_665 ?
C8 N1 C5 129.5(3) . . ?
C8 N1 N2 109.4(3) . . ?
N2 N1 C5 120.9(3) . . ?
N3 C8 N1 110.4(3) . . ?
O1 C1 C2 117.8(2) . . ?
O2 C1 O1 122.2(3) . . ?
O2 C1 C2 120.0(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 C7 118.5(3) . . ?
C7 C2 C1 120.2(3) . . ?
C4 C5 N1 119.5(3) . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 N1 119.7(3) . . ?
C5 C4 C3 119.6(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C7 C6 121.5(3) . . ?
C5 C6 C7 118.9(3) . . ?
C9 N2 N1 102.9(3) . . ?
N2 C9 N3 114.5(3) . . ?

_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 -0.020 0.750 318 42 ' '
2 0.750 -0.018 0.250 318 42 ' '





