# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_skkar40
_database_code_depnum_ccdc_archive 'CCDC 945288'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cu N5 O6'
_chemical_formula_weight         360.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3423(3)
_cell_length_b                   8.8649(4)
_cell_length_c                   11.4482(5)
_cell_angle_alpha                89.440(4)
_cell_angle_beta                 80.271(3)
_cell_angle_gamma                67.287(3)
_cell_volume                     676.22(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3449
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      64.66

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4777
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         64.70
_reflns_number_total             2014
_reflns_number_gt                1805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0609P)²+1.9535P] 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         2014
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_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 0.50067(8) 0.01560(7) 0.25363(5) 0.0202(2) Uani 1 1 d . . .
O5 O 0.6912(4) -0.1727(4) 0.1440(3) 0.0270(7) Uani 1 1 d . . .
O4 O 0.4041(4) -0.0937(4) 0.0859(3) 0.0274(7) Uani 1 1 d . . .
O6 O 0.6639(5) -0.2914(4) -0.0133(3) 0.0321(8) Uani 1 1 d . . .
O2 O 0.4011(5) -0.1298(4) 0.3522(3) 0.0276(7) Uani 1 1 d . . .
O3 O 0.5245(5) -0.2927(4) 0.4879(3) 0.0360(8) Uani 1 1 d . . .
O1 O 0.6679(4) -0.1309(4) 0.4097(3) 0.0253(7) Uani 1 1 d . . .
N5 N 0.5843(6) -0.1873(4) 0.0693(3) 0.0234(8) Uani 1 1 d . . .
N4 N 0.5340(5) -0.1874(4) 0.4199(3) 0.0239(9) Uani 1 1 d . . .
N2 N 0.3326(5) 0.3570(4) 0.2672(3) 0.0192(8) Uani 1 1 d . . .
N3 N 0.6412(6) 0.1588(5) 0.1933(3) 0.0263(9) Uani 1 1 d . . .
C4 C 0.5327(7) 0.3205(6) 0.2139(4) 0.0275(11) Uani 1 1 d . . .
C5 C 0.6086(7) 0.4381(5) 0.1836(4) 0.0250(10) Uani 1 1 d . . .
H5A H 0.5282 0.5517 0.1986 0.030 Uiso 1 1 calc R . .
C6 C 0.8106(7) 0.3813(6) 0.1294(4) 0.0310(11) Uani 1 1 d . . .
H6A H 0.8707 0.4574 0.1077 0.037 Uiso 1 1 calc R . .
C7 C 0.9235(7) 0.2153(6) 0.1072(4) 0.0311(11) Uani 1 1 d . . .
H7A H 1.0601 0.1763 0.0692 0.037 Uiso 1 1 calc R . .
C8 C 0.8343(6) 0.1101(6) 0.1411(4) 0.0284(11) Uani 1 1 d . . .
H8A H 0.9124 -0.0041 0.1273 0.034 Uiso 1 1 calc R . .
C3 C 0.1653(7) 0.5009(6) 0.2934(4) 0.0288(11) Uani 1 1 d . . .
C2 C 0.0128(6) 0.4568(5) 0.3523(4) 0.0264(10) Uani 1 1 d . . .
H2A H -0.1219 0.5286 0.3820 0.032 Uiso 1 1 calc R . .
C1 C 0.0949(6) 0.2880(6) 0.3596(4) 0.0263(10) Uani 1 1 d . . .
N1 N 0.2856(5) 0.2264(5) 0.3089(3) 0.0276(9) Uani 1 1 d . . .
C9 C -0.0092(7) 0.1825(6) 0.4145(4) 0.0332(11) Uani 1 1 d . . .
H9A H 0.0322 0.0826 0.3635 0.050 Uiso 1 1 calc R . .
H9B H -0.1547 0.2425 0.4233 0.050 Uiso 1 1 calc R . .
H9C H 0.0267 0.1533 0.4927 0.050 Uiso 1 1 calc R . .
C10 C 0.1566(7) 0.6640(5) 0.2531(5) 0.0320(11) Uani 1 1 d . . .
H10A H 0.2120 0.6540 0.1681 0.048 Uiso 1 1 calc R . .
H10B H 0.2353 0.7023 0.2975 0.048 Uiso 1 1 calc R . .
H10C H 0.0168 0.7429 0.2673 0.048 Uiso 1 1 calc R . .


_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 N1 1.947(4) . ?
Cu1 O2 1.972(3) . ?
Cu1 N3 1.976(4) . ?
Cu1 O5 1.991(3) . ?
Cu1 O1 2.419(3) . ?
O5 N5 1.293(5) . ?
O4 N5 1.243(5) . ?
O6 N5 1.225(5) . ?
O2 N4 1.294(4) . ?
O3 N4 1.225(5) . ?
O1 N4 1.253(5) . ?
N2 C3 1.378(5) . ?
N2 N1 1.389(5) . ?
N2 C4 1.404(6) . ?
N3 C8 1.342(6) . ?
N3 C4 1.344(6) . ?
C4 C5 1.376(7) . ?
C5 C6 1.399(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.382(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.353(7) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C3 C2 1.393(7) . ?
C3 C10 1.494(7) . ?
C2 C1 1.389(6) . ?
C2 H2A 0.9500 . ?
C1 N1 1.318(6) . ?
C1 C9 1.494(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
N1 Cu1 O2 99.71(15) . . ?
N1 Cu1 N3 81.54(16) . . ?
O2 Cu1 N3 163.45(14) . . ?
N1 Cu1 O5 160.05(14) . . ?
O2 Cu1 O5 91.37(13) . . ?
N3 Cu1 O5 92.55(14) . . ?
N1 Cu1 O1 113.49(13) . . ?
O2 Cu1 O1 58.04(11) . . ?
N3 Cu1 O1 106.17(13) . . ?
O5 Cu1 O1 86.44(11) . . ?
N5 O5 Cu1 103.6(2) . . ?
N4 O2 Cu1 102.5(3) . . ?
N4 O1 Cu1 82.8(2) . . ?
O6 N5 O4 123.4(4) . . ?
O6 N5 O5 119.1(3) . . ?
O4 N5 O5 117.5(3) . . ?
O3 N4 O1 124.0(4) . . ?
O3 N4 O2 119.6(4) . . ?
O1 N4 O2 116.5(3) . . ?
C3 N2 N1 109.7(3) . . ?
C3 N2 C4 133.4(4) . . ?
N1 N2 C4 116.8(3) . . ?
C8 N3 C4 117.9(4) . . ?
C8 N3 Cu1 126.5(3) . . ?
C4 N3 Cu1 115.5(3) . . ?
N3 C4 C5 123.6(4) . . ?
N3 C4 N2 112.9(4) . . ?
C5 C4 N2 123.5(4) . . ?
C4 C5 C6 116.4(4) . . ?
C4 C5 H5A 121.8 . . ?
C6 C5 H5A 121.8 . . ?
C7 C6 C5 120.6(5) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C6 118.2(4) . . ?
C8 C7 H7A 120.9 . . ?
C6 C7 H7A 120.9 . . ?
N3 C8 C7 123.3(4) . . ?
N3 C8 H8A 118.4 . . ?
C7 C8 H8A 118.4 . . ?
N2 C3 C2 105.8(4) . . ?
N2 C3 C10 124.3(4) . . ?
C2 C3 C10 129.7(4) . . ?
C1 C2 C3 107.0(4) . . ?
C1 C2 H2A 126.5 . . ?
C3 C2 H2A 126.5 . . ?
N1 C1 C2 110.7(4) . . ?
N1 C1 C9 122.0(4) . . ?
C2 C1 C9 127.3(4) . . ?
C1 N1 N2 106.8(4) . . ?
C1 N1 Cu1 139.9(4) . . ?
N2 N1 Cu1 112.2(3) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.880
_diffrn_reflns_theta_full        64.70
_diffrn_measured_fraction_theta_full 0.880
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_8novc
_database_code_depnum_ccdc_archive 'CCDC 945289'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H11 Cu1 N3 O4), H2 O'
_chemical_formula_sum            'C24 H24 Cu2 N6 O9'
_chemical_formula_weight         667.59

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           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   20.402(5)
_cell_length_b                   7.233(5)
_cell_length_c                   18.215(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 112.363(5)
_cell_angle_gamma                90.000
_cell_volume                     2485.8(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2754
_cell_measurement_theta_min      0.808
_cell_measurement_theta_max      28.30

_exptl_crystal_description       none
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8148
_exptl_absorpt_correction_T_max  0.8707
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7801
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unet/netI      0.0285
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3077
_reflns_number_gt                2754
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

__refine_special_details         
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)²+6.5150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.009

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 0.727515(13) 0.09373(4) 0.633084(15) 0.01082(11) Uani 1 1 d . . .
O1 O 0.81878(9) 0.3242(2) 0.84234(10) 0.0163(3) Uani 1 1 d . . .
O2 O 0.73495(8) 0.2296(2) 0.72845(10) 0.0153(3) Uani 1 1 d . . .
O3 O 0.91510(9) 0.1151(3) 0.80281(10) 0.0191(4) Uani 1 1 d . . .
O4 O 0.82796(8) 0.0562(2) 0.68623(10) 0.0153(3) Uani 1 1 d . . .
O5 O 1.0000 -0.1286(4) 0.7500 0.0380(8) Uani 1 2 d S . .
N1 N 0.62716(10) 0.1665(3) 0.57379(11) 0.0117(4) Uani 1 1 d . . .
N2 N 0.65211(10) 0.0693(3) 0.46695(11) 0.0131(4) Uani 1 1 d . . .
N3 N 0.71955(10) 0.0406(3) 0.52293(11) 0.0122(4) Uani 1 1 d . . .
C1 C 0.58417(12) 0.2353(3) 0.60795(14) 0.0151(5) Uani 1 1 d . . .
H1 H 0.6022 0.2536 0.6626 0.018 Uiso 1 1 calc R . .
C2 C 0.51426(12) 0.2794(3) 0.56433(15) 0.0172(5) Uani 1 1 d . . .
H2 H 0.4854 0.3260 0.5890 0.021 Uiso 1 1 calc R . .
C3 C 0.48797(12) 0.2524(3) 0.48262(15) 0.0168(5) Uani 1 1 d . . .
H3 H 0.4411 0.2818 0.4519 0.020 Uiso 1 1 calc R . .
C4 C 0.53174(12) 0.1817(3) 0.44720(14) 0.0166(5) Uani 1 1 d . . .
H4 H 0.5149 0.1630 0.3926 0.020 Uiso 1 1 calc R . .
C5 C 0.60122(12) 0.1395(3) 0.49497(13) 0.0126(4) Uani 1 1 d . . .
C6 C 0.75805(12) -0.0203(3) 0.48291(14) 0.0142(4) Uani 1 1 d . . .
C7 C 0.71567(13) -0.0305(3) 0.40160(14) 0.0176(5) Uani 1 1 d . . .
H7 H 0.7302 -0.0685 0.3614 0.021 Uiso 1 1 calc R . .
C8 C 0.64914(13) 0.0257(3) 0.39251(14) 0.0156(5) Uani 1 1 d . . .
C9 C 0.58441(14) 0.0324(4) 0.31782(14) 0.0206(5) Uani 1 1 d . . .
H9A H 0.5451 0.0776 0.3294 0.031 Uiso 1 1 calc R . .
H9B H 0.5738 -0.0895 0.2956 0.031 Uiso 1 1 calc R . .
H9C H 0.5926 0.1135 0.2805 0.031 Uiso 1 1 calc R . .
C10 C 0.83442(13) -0.0695(3) 0.52295(15) 0.0176(5) Uani 1 1 d . . .
H10A H 0.8494 -0.0487 0.5790 0.026 Uiso 1 1 calc R . .
H10B H 0.8621 0.0059 0.5022 0.026 Uiso 1 1 calc R . .
H10C H 0.8410 -0.1974 0.5135 0.026 Uiso 1 1 calc R . .
C11 C 0.85340(12) 0.1269(3) 0.75611(14) 0.0132(4) Uani 1 1 d . . .
C12 C 0.79857(12) 0.2381(3) 0.77908(13) 0.0123(4) Uani 1 1 d . . .
H1W1 H 0.975(2) -0.052(5) 0.760(2) 0.042(11) Uiso 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 O4 1.9238(17) . ?
Cu1 O2 1.9509(17) . ?
Cu1 N3 1.988(2) . ?
Cu1 N1 1.9882(19) . ?
Cu1 O1 2.283(2) 4_646 ?
O1 C12 1.235(3) . ?
O1 Cu1 2.283(2) 4_656 ?
O2 C12 1.276(3) . ?
O3 C11 1.225(3) . ?
O4 C11 1.284(3) . ?
N1 C5 1.342(3) . ?
N1 C1 1.349(3) . ?
N2 C8 1.371(3) . ?
N2 N3 1.381(3) . ?
N2 C5 1.414(3) . ?
N3 C6 1.334(3) . ?
C1 C2 1.380(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.383(4) . ?
C4 C5 1.386(3) . ?
C6 C7 1.404(3) . ?
C6 C10 1.490(3) . ?
C7 C8 1.365(3) . ?
C8 C9 1.493(3) . ?
C11 C12 1.559(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
O4 Cu1 O2 85.18(7) . . ?
O4 Cu1 N3 98.22(7) . . ?
O2 Cu1 N3 160.90(8) . . ?
O4 Cu1 N1 172.06(8) . . ?
O2 Cu1 N1 93.75(7) . . ?
N3 Cu1 N1 80.27(8) . . ?
O4 Cu1 O1 102.81(7) . 4_646 ?
O2 Cu1 O1 98.82(8) . 4_646 ?
N3 Cu1 O1 98.72(7) . 4_646 ?
N1 Cu1 O1 85.13(7) . 4_646 ?
C12 O1 Cu1 126.68(15) . 4_656 ?
C12 O2 Cu1 112.40(14) . . ?
C11 O4 Cu1 113.21(14) . . ?
C5 N1 C1 119.1(2) . . ?
C5 N1 Cu1 116.62(15) . . ?
C1 N1 Cu1 124.26(16) . . ?
C8 N2 N3 110.63(19) . . ?
C8 N2 C5 132.6(2) . . ?
N3 N2 C5 116.71(18) . . ?
C6 N3 N2 105.93(18) . . ?
C6 N3 Cu1 140.96(16) . . ?
N2 N3 Cu1 113.08(14) . . ?
N1 C1 C2 122.0(2) . . ?
C1 C2 C3 118.5(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 118.4(2) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 N2 113.17(19) . . ?
C4 C5 N2 124.6(2) . . ?
N3 C6 C7 109.8(2) . . ?
N3 C6 C10 122.3(2) . . ?
C7 C6 C10 127.8(2) . . ?
C8 C7 C6 107.3(2) . . ?
C7 C8 N2 106.3(2) . . ?
C7 C8 C9 127.9(2) . . ?
N2 C8 C9 125.8(2) . . ?
O3 C11 O4 125.6(2) . . ?
O3 C11 C12 120.1(2) . . ?
O4 C11 C12 114.27(19) . . ?
O1 C12 O2 125.9(2) . . ?
O1 C12 C11 119.5(2) . . ?
O2 C12 C11 114.68(19) . . ?

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
O4 Cu1 O2 C12 1.95(16) . . . . ?
N3 Cu1 O2 C12 -99.3(3) . . . . ?
N1 Cu1 O2 C12 -170.15(16) . . . . ?
O1 Cu1 O2 C12 104.20(16) 4_646 . . . ?
O2 Cu1 O4 C11 1.59(16) . . . . ?
N3 Cu1 O4 C11 162.67(16) . . . . ?
O1 Cu1 O4 C11 -96.38(17) 4_646 . . . ?
O4 Cu1 N1 C5 83.0(6) . . . . ?
O2 Cu1 N1 C5 165.05(17) . . . . ?
N3 Cu1 N1 C5 3.33(17) . . . . ?
O1 Cu1 N1 C5 -96.40(17) 4_646 . . . ?
O4 Cu1 N1 C1 -98.8(5) . . . . ?
O2 Cu1 N1 C1 -16.8(2) . . . . ?
N3 Cu1 N1 C1 -178.5(2) . . . . ?
O1 Cu1 N1 C1 81.78(19) 4_646 . . . ?
C8 N2 N3 C6 0.1(3) . . . . ?
C5 N2 N3 C6 -178.41(19) . . . . ?
C8 N2 N3 Cu1 -178.31(15) . . . . ?
C5 N2 N3 Cu1 3.2(2) . . . . ?
O4 Cu1 N3 C6 6.9(3) . . . . ?
O2 Cu1 N3 C6 106.0(3) . . . . ?
N1 Cu1 N3 C6 179.0(3) . . . . ?
O1 Cu1 N3 C6 -97.5(3) 4_646 . . . ?
O4 Cu1 N3 N2 -175.50(15) . . . . ?
O2 Cu1 N3 N2 -76.4(3) . . . . ?
N1 Cu1 N3 N2 -3.40(15) . . . . ?
O1 Cu1 N3 N2 80.09(15) 4_646 . . . ?
C5 N1 C1 C2 -0.2(4) . . . . ?
Cu1 N1 C1 C2 -178.31(18) . . . . ?
N1 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C1 N1 C5 C4 0.6(3) . . . . ?
Cu1 N1 C5 C4 178.93(18) . . . . ?
C1 N1 C5 N2 179.2(2) . . . . ?
Cu1 N1 C5 N2 -2.5(3) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C3 C4 C5 N2 -179.0(2) . . . . ?
C8 N2 C5 N1 -178.6(2) . . . . ?
N3 N2 C5 N1 -0.5(3) . . . . ?
C8 N2 C5 C4 -0.1(4) . . . . ?
N3 N2 C5 C4 178.0(2) . . . . ?
N2 N3 C6 C7 0.1(3) . . . . ?
Cu1 N3 C6 C7 177.77(19) . . . . ?
N2 N3 C6 C10 -179.3(2) . . . . ?
Cu1 N3 C6 C10 -1.6(4) . . . . ?
N3 C6 C7 C8 -0.2(3) . . . . ?
C10 C6 C7 C8 179.1(2) . . . . ?
C6 C7 C8 N2 0.3(3) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
N3 N2 C8 C7 -0.3(3) . . . . ?
C5 N2 C8 C7 177.9(2) . . . . ?
N3 N2 C8 C9 177.5(2) . . . . ?
C5 N2 C8 C9 -4.3(4) . . . . ?
Cu1 O4 C11 O3 176.9(2) . . . . ?
Cu1 O4 C11 C12 -4.2(2) . . . . ?
Cu1 O1 C12 O2 -32.2(3) 4_656 . . . ?
Cu1 O1 C12 C11 147.99(16) 4_656 . . . ?
Cu1 O2 C12 O1 175.68(19) . . . . ?
Cu1 O2 C12 C11 -4.5(2) . . . . ?
O3 C11 C12 O1 4.8(3) . . . . ?
O4 C11 C12 O1 -174.2(2) . . . . ?
O3 C11 C12 O2 -175.0(2) . . . . ?
O4 C11 C12 O2 6.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.105
