# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_thiaa
_database_code_depnum_ccdc_archive 'CCDC 911568'
#TrackingRef 'web_deposit_cif_file_0_NoraKulak_1353334570.THIAA.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H19 Cu N5 O6 S'
_chemical_formula_weight         376.88
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'
S S 0.1246 0.1234 '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   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   8.5321(16)
_cell_length_b                   11.903(2)
_cell_length_c                   14.168(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.368(4)
_cell_angle_gamma                90.00
_cell_volume                     1434.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    958
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      30.5
_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMRT CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17105
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         30.56
_reflns_number_total             4381
_reflns_number_gt                4070
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0211P)^2^+1.4461P] where P=(Fo^2^+2Fc^2^)/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         4381
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
H3 H 0.466(3) 0.789(2) 0.0163(17) 0.030(6) Uiso 1 1 d . . .
H2 H 0.283(3) 1.008(2) 0.1368(16) 0.025(5) Uiso 1 1 d . . .
H1 H -0.067(3) 0.8775(19) 0.0973(15) 0.023(5) Uiso 1 1 d . . .
Cu1 Cu 0.20373(2) 0.835269(14) 0.058170(12) 0.01305(5) Uani 1 1 d . . .
S2 S 0.14371(4) 0.65871(3) -0.00545(3) 0.01771(7) Uani 1 1 d . . .
C1 C 0.03092(18) 0.62527(13) 0.09471(11) 0.0190(3) Uani 1 1 d . . .
H1A H -0.0240 0.5526 0.0842 0.023 Uiso 1 1 calc R . .
H1B H 0.1013 0.6198 0.1534 0.023 Uiso 1 1 calc R . .
C2 C -0.08762(17) 0.71970(13) 0.10310(11) 0.0194(3) Uani 1 1 d . . .
H2A H -0.1594 0.7226 0.0449 0.023 Uiso 1 1 calc R . .
H2B H -0.1514 0.7045 0.1572 0.023 Uiso 1 1 calc R . .
C3 C 0.03915(18) 0.85455(13) 0.21880(10) 0.0187(3) Uani 1 1 d . . .
H3A H 0.1007 0.7914 0.2481 0.022 Uiso 1 1 calc R . .
H3B H -0.0555 0.8656 0.2540 0.022 Uiso 1 1 calc R . .
C4 C 0.13755(19) 0.96063(14) 0.22193(11) 0.0209(3) Uani 1 1 d . . .
H4A H 0.0714 1.0255 0.2005 0.025 Uiso 1 1 calc R . .
H4B H 0.1806 0.9753 0.2876 0.025 Uiso 1 1 calc R . .
C5 C 0.41473(18) 0.90351(14) 0.20880(10) 0.0193(3) Uani 1 1 d . . .
H5A H 0.3914 0.8399 0.2505 0.023 Uiso 1 1 calc R . .
H5B H 0.4673 0.9633 0.2481 0.023 Uiso 1 1 calc R . .
C6 C 0.51997(18) 0.86506(14) 0.13355(11) 0.0200(3) Uani 1 1 d . . .
H6A H 0.5552 0.9307 0.0979 0.024 Uiso 1 1 calc R . .
H6B H 0.6141 0.8269 0.1636 0.024 Uiso 1 1 calc R . .
C7 C 0.43334(19) 0.66801(13) 0.09946(12) 0.0209(3) Uani 1 1 d . . .
H7A H 0.3888 0.6619 0.1618 0.025 Uiso 1 1 calc R . .
H7B H 0.5429 0.6401 0.1061 0.025 Uiso 1 1 calc R . .
C8 C 0.33643(19) 0.59798(13) 0.02633(12) 0.0226(3) Uani 1 1 d . . .
H8A H 0.3228 0.5215 0.0519 0.027 Uiso 1 1 calc R . .
H8B H 0.3944 0.5911 -0.0313 0.027 Uiso 1 1 calc R . .
N1 N -0.00709(15) 0.82970(11) 0.11729(9) 0.0163(2) Uani 1 1 d . . .
N2 N 0.26759(15) 0.94690(11) 0.15965(9) 0.0163(2) Uani 1 1 d . . .
N3 N 0.43084(15) 0.78645(11) 0.06814(9) 0.0159(2) Uani 1 1 d . . .
N4 N 0.24182(15) 0.90370(11) -0.14121(9) 0.0170(2) Uani 1 1 d . . .
O1 O 0.18157(14) 0.93999(10) -0.06661(8) 0.0198(2) Uani 1 1 d . . .
O2 O 0.31206(15) 0.81236(11) -0.13941(9) 0.0262(3) Uani 1 1 d . . .
O3 O 0.22793(15) 0.96206(11) -0.21391(8) 0.0244(2) Uani 1 1 d . . .
N5 N 0.32317(16) 0.23142(11) 0.12300(10) 0.0200(2) Uani 1 1 d . . .
O4 O 0.32757(17) 0.15391(10) 0.06228(8) 0.0261(3) Uani 1 1 d . . .
O5 O 0.35334(18) 0.32930(11) 0.09947(11) 0.0335(3) Uani 1 1 d . . .
O6 O 0.2905(2) 0.20761(13) 0.20428(9) 0.0379(3) Uani 1 1 d . . .
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 0.01422(8) 0.01181(8) 0.01330(8) 0.00051(6) 0.00210(6) -0.00001(6)
S2 0.02040(16) 0.01528(16) 0.01775(16) -0.00211(12) 0.00344(12) -0.00328(13)
C1 0.0208(7) 0.0166(7) 0.0200(6) 0.0013(5) 0.0030(5) -0.0042(5)
C2 0.0157(6) 0.0221(7) 0.0205(7) 0.0010(5) 0.0017(5) -0.0030(5)
C3 0.0209(7) 0.0190(7) 0.0168(6) 0.0002(5) 0.0056(5) -0.0003(5)
C4 0.0230(7) 0.0188(7) 0.0219(7) -0.0046(5) 0.0076(6) -0.0011(6)
C5 0.0197(7) 0.0216(7) 0.0163(6) -0.0011(5) -0.0002(5) -0.0022(5)
C6 0.0158(6) 0.0212(7) 0.0230(7) -0.0016(6) 0.0018(5) -0.0031(5)
C7 0.0183(6) 0.0160(7) 0.0284(7) 0.0039(6) 0.0021(6) 0.0025(5)
C8 0.0224(7) 0.0138(7) 0.0324(8) -0.0018(6) 0.0069(6) 0.0019(5)
N1 0.0154(5) 0.0162(6) 0.0176(5) 0.0028(4) 0.0026(4) 0.0024(5)
N2 0.0192(6) 0.0135(6) 0.0168(5) -0.0004(4) 0.0043(4) -0.0008(4)
N3 0.0161(5) 0.0158(6) 0.0161(5) 0.0002(4) 0.0037(4) -0.0006(4)
N4 0.0167(5) 0.0198(6) 0.0144(5) -0.0011(4) -0.0002(4) -0.0040(5)
O1 0.0271(5) 0.0175(5) 0.0153(5) 0.0004(4) 0.0054(4) 0.0032(4)
O2 0.0317(6) 0.0241(6) 0.0235(6) -0.0022(5) 0.0073(5) 0.0079(5)
O3 0.0289(6) 0.0302(6) 0.0139(5) 0.0051(4) 0.0004(4) -0.0013(5)
N5 0.0213(6) 0.0174(6) 0.0215(6) -0.0010(5) 0.0033(5) -0.0015(5)
O4 0.0400(7) 0.0191(6) 0.0202(5) -0.0031(4) 0.0095(5) -0.0040(5)
O5 0.0432(8) 0.0158(6) 0.0407(8) 0.0029(5) -0.0015(6) -0.0050(5)
O6 0.0576(9) 0.0355(8) 0.0230(6) -0.0064(5) 0.0193(6) -0.0108(7)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.0027(13) . ?
Cu1 N3 2.0176(13) . ?
Cu1 N1 2.0423(13) . ?
Cu1 O1 2.1596(11) . ?
Cu1 S2 2.3283(5) . ?
S2 C1 1.8184(16) . ?
S2 C8 1.8211(17) . ?
C1 C2 1.523(2) . ?
C2 N1 1.485(2) . ?
C3 N1 1.492(2) . ?
C3 C4 1.515(2) . ?
C4 N2 1.4782(19) . ?
C5 N2 1.481(2) . ?
C5 C6 1.516(2) . ?
C6 N3 1.485(2) . ?
C7 N3 1.478(2) . ?
C7 C8 1.524(2) . ?
N4 O3 1.2406(17) . ?
N4 O2 1.2408(18) . ?
N4 O1 1.2848(16) . ?
N5 O6 1.2383(18) . ?
N5 O5 1.2442(18) . ?
N5 O4 1.2640(17) . ?
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
N2 Cu1 N3 86.19(5) . . ?
N2 Cu1 N1 85.81(5) . . ?
N3 Cu1 N1 146.42(5) . . ?
N2 Cu1 O1 101.94(5) . . ?
N3 Cu1 O1 104.32(5) . . ?
N1 Cu1 O1 109.24(5) . . ?
N2 Cu1 S2 156.44(4) . . ?
N3 Cu1 S2 87.07(4) . . ?
N1 Cu1 S2 87.42(4) . . ?
O1 Cu1 S2 101.60(3) . . ?
C1 S2 C8 103.98(8) . . ?
C1 S2 Cu1 90.53(5) . . ?
C8 S2 Cu1 95.44(5) . . ?
C2 C1 S2 107.06(10) . . ?
N1 C2 C1 110.99(12) . . ?
N1 C3 C4 107.38(12) . . ?
N2 C4 C3 109.26(12) . . ?
N2 C5 C6 107.51(12) . . ?
N3 C6 C5 109.06(12) . . ?
N3 C7 C8 108.85(13) . . ?
C7 C8 S2 112.58(11) . . ?
C2 N1 C3 113.02(12) . . ?
C2 N1 Cu1 112.70(9) . . ?
C3 N1 Cu1 102.27(9) . . ?
C4 N2 C5 113.93(12) . . ?
C4 N2 Cu1 109.05(10) . . ?
C5 N2 Cu1 106.30(9) . . ?
C7 N3 C6 114.75(12) . . ?
C7 N3 Cu1 106.71(9) . . ?
C6 N3 Cu1 107.80(9) . . ?
O3 N4 O2 121.54(13) . . ?
O3 N4 O1 118.42(13) . . ?
O2 N4 O1 120.04(13) . . ?
N4 O1 Cu1 117.63(9) . . ?
O6 N5 O5 121.96(15) . . ?
O6 N5 O4 119.11(14) . . ?
O5 N5 O4 118.93(14) . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.063


data_oxaa
_database_code_depnum_ccdc_archive 'CCDC 911569'
#TrackingRef 'web_deposit_cif_file_1_NoraKulak_1353334570.OXAA_final.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H19 Cu N5 O7'
_chemical_formula_weight         360.82
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   P2(1)/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   7.9211(19)
_cell_length_b                   11.979(3)
_cell_length_c                   14.757(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.587(5)
_cell_angle_gamma                90.00
_cell_volume                     1398.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    1010
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      30.4
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17378
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         30.56
_reflns_number_total             4238
_reflns_number_gt                3523
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (BRUker-AXS)'
_computing_data_reduction        'SAINT (BRUker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0321P)^2^+0.8704P] where P=(Fo^2^+2Fc^2^)/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         4238
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.002
_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
Cu01 Cu 0.88597(2) 1.026783(17) 0.710591(12) 0.01336(6) Uani 1 1 d . . .
C1 C 0.66984(19) 0.98534(15) 0.86489(10) 0.0178(3) Uani 1 1 d . . .
H1A H 0.6723 0.9033 0.8569 0.021 Uiso 1 1 calc R . .
H1B H 0.5784 1.0042 0.9058 0.021 Uiso 1 1 calc R . .
C2 C 0.83872(19) 1.02639(15) 0.90470(10) 0.0172(3) Uani 1 1 d . . .
H2A H 0.8273 1.1056 0.9227 0.021 Uiso 1 1 calc R . .
H2B H 0.8689 0.9829 0.9601 0.021 Uiso 1 1 calc R . .
C3 C 1.07715(19) 0.91121(15) 0.84750(11) 0.0181(3) Uani 1 1 d . . .
H3A H 1.0856 0.8862 0.9115 0.022 Uiso 1 1 calc R . .
H3B H 1.1930 0.9247 0.8275 0.022 Uiso 1 1 calc R . .
C4 C 0.9937(2) 0.82074(14) 0.78925(11) 0.0176(3) Uani 1 1 d . . .
H4A H 1.0704 0.7560 0.7848 0.021 Uiso 1 1 calc R . .
H4B H 0.8883 0.7953 0.8164 0.021 Uiso 1 1 calc R . .
C5 C 0.8257(2) 0.80988(15) 0.64111(11) 0.0198(3) Uani 1 1 d . . .
H5A H 0.7286 0.7895 0.6777 0.024 Uiso 1 1 calc R . .
H5B H 0.8735 0.7406 0.6161 0.024 Uiso 1 1 calc R . .
C7 C 0.7687(2) 0.88762(15) 0.56472(11) 0.0220(3) Uani 1 1 d . . .
H7A H 0.8585 0.8929 0.5204 0.026 Uiso 1 1 calc R . .
H7B H 0.6663 0.8567 0.5330 0.026 Uiso 1 1 calc R . .
C8 C 0.5529(2) 1.02209(16) 0.62327(11) 0.0195(3) Uani 1 1 d . . .
H8A H 0.4765 0.9809 0.5801 0.023 Uiso 1 1 calc R . .
H8B H 0.5279 1.1027 0.6162 0.023 Uiso 1 1 calc R . .
C9 C 0.51695(19) 0.98668(16) 0.71929(11) 0.0190(3) Uani 1 1 d . . .
H9A H 0.4019 1.0103 0.7346 0.023 Uiso 1 1 calc R . .
H9B H 0.5246 0.9045 0.7252 0.023 Uiso 1 1 calc R . .
H1 H 1.042(3) 1.067(2) 0.8512(15) 0.027(6) Uiso 1 1 d . . .
H2 H 1.048(3) 0.8690(19) 0.6701(15) 0.030(6) Uiso 1 1 d . . .
H3 H 0.753(3) 1.0446(17) 0.5596(15) 0.015(5) Uiso 1 1 d . . .
N1 N 0.97823(17) 1.01664(12) 0.84068(9) 0.0153(3) Uani 1 1 d . . .
N2 N 0.95545(17) 0.86861(12) 0.69830(9) 0.0155(3) Uani 1 1 d . . .
N3 N 0.73089(17) 1.00131(12) 0.59988(10) 0.0166(3) Uani 1 1 d . . .
N4 N 1.05731(16) 1.19719(12) 0.65037(9) 0.0173(3) Uani 1 1 d . . .
N5 N 0.28804(18) 0.76029(13) 0.56882(10) 0.0208(3) Uani 1 1 d . . .
O1 O 0.64104(13) 1.03940(10) 0.77883(7) 0.0164(2) Uani 1 1 d . . .
O2 O 0.91384(13) 1.19310(10) 0.68905(8) 0.0182(2) Uani 1 1 d . . .
O3 O 1.14167(15) 1.10955(11) 0.64814(9) 0.0232(3) Uani 1 1 d . . .
O4 O 1.10379(17) 1.28483(12) 0.61712(10) 0.0307(3) Uani 1 1 d . . .
O5 O 0.20704(16) 0.85030(11) 0.55784(9) 0.0266(3) Uani 1 1 d . . .
O6 O 0.2594(2) 0.70023(15) 0.63526(11) 0.0450(4) Uani 1 1 d . . .
O7 O 0.39536(18) 0.73275(13) 0.51451(10) 0.0364(4) Uani 1 1 d . . .
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
Cu01 0.01578(9) 0.01119(10) 0.01302(9) 0.00066(7) -0.00036(6) -0.00111(7)
C1 0.0172(6) 0.0219(9) 0.0144(7) 0.0024(6) 0.0016(5) -0.0001(6)
C2 0.0197(6) 0.0194(8) 0.0124(6) -0.0008(6) -0.0002(5) 0.0019(6)
C3 0.0178(6) 0.0191(9) 0.0174(7) 0.0017(6) -0.0018(5) 0.0028(6)
C4 0.0210(7) 0.0145(8) 0.0172(7) 0.0022(6) 0.0012(5) 0.0021(6)
C5 0.0237(7) 0.0142(8) 0.0213(8) -0.0032(6) -0.0005(6) -0.0017(6)
C7 0.0300(8) 0.0188(9) 0.0169(7) -0.0040(6) -0.0017(6) -0.0012(7)
C8 0.0184(7) 0.0220(9) 0.0177(7) 0.0015(7) -0.0040(5) -0.0011(6)
C9 0.0149(6) 0.0239(9) 0.0180(7) 0.0004(6) -0.0023(5) -0.0037(6)
N1 0.0169(5) 0.0129(7) 0.0161(6) -0.0003(5) -0.0005(5) -0.0018(5)
N2 0.0180(6) 0.0140(7) 0.0148(6) 0.0001(5) 0.0019(5) -0.0016(5)
N3 0.0204(6) 0.0152(7) 0.0141(6) 0.0025(5) -0.0001(5) -0.0019(5)
N4 0.0162(5) 0.0156(7) 0.0202(6) -0.0004(5) 0.0023(5) -0.0026(5)
N5 0.0205(6) 0.0194(8) 0.0228(7) -0.0002(6) 0.0035(5) 0.0028(5)
O1 0.0160(5) 0.0187(6) 0.0142(5) 0.0012(4) -0.0011(4) -0.0018(4)
O2 0.0160(5) 0.0138(6) 0.0254(6) 0.0007(5) 0.0053(4) -0.0007(4)
O3 0.0227(5) 0.0189(7) 0.0285(6) 0.0015(5) 0.0077(5) 0.0048(5)
O4 0.0284(6) 0.0172(7) 0.0474(8) 0.0072(6) 0.0105(6) -0.0070(5)
O5 0.0320(6) 0.0201(7) 0.0286(7) 0.0078(5) 0.0105(5) 0.0083(5)
O6 0.0547(9) 0.0406(10) 0.0414(9) 0.0241(7) 0.0210(7) 0.0244(8)
O7 0.0361(7) 0.0348(9) 0.0398(8) -0.0032(7) 0.0183(6) 0.0084(6)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 N2 1.9837(15) . ?
Cu01 N3 2.0224(15) . ?
Cu01 N1 2.0267(14) . ?
Cu01 O2 2.0312(13) . ?
Cu01 O1 2.2310(12) . ?
C1 O1 1.4347(19) . ?
C1 C2 1.518(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.491(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.487(2) . ?
C3 C4 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.478(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.478(2) . ?
C5 C7 1.515(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 N3 1.493(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.488(2) . ?
C8 C9 1.518(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.4348(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 H1 0.80(2) . ?
N2 H2 0.86(2) . ?
N3 H3 0.81(2) . ?
N4 O4 1.2227(19) . ?
N4 O3 1.2457(19) . ?
N4 O2 1.2955(17) . ?
N5 O7 1.2390(19) . ?
N5 O6 1.245(2) . ?
N5 O5 1.261(2) . ?
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
N2 Cu01 N3 86.73(6) . . ?
N2 Cu01 N1 86.54(6) . . ?
N3 Cu01 N1 159.40(6) . . ?
N2 Cu01 O2 152.88(5) . . ?
N3 Cu01 O2 95.04(5) . . ?
N1 Cu01 O2 99.78(5) . . ?
N2 Cu01 O1 110.88(5) . . ?
N3 Cu01 O1 82.29(5) . . ?
N1 Cu01 O1 81.97(5) . . ?
O2 Cu01 O1 96.15(4) . . ?
O1 C1 C2 107.37(13) . . ?
O1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N1 C2 C1 113.26(13) . . ?
N1 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C4 110.72(13) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N2 C4 C3 107.68(13) . . ?
N2 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
N2 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N2 C5 C7 107.96(14) . . ?
N2 C5 H5A 110.1 . . ?
C7 C5 H5A 110.1 . . ?
N2 C5 H5B 110.1 . . ?
C7 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N3 C7 C5 111.10(13) . . ?
N3 C7 H7A 109.4 . . ?
C5 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C5 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N3 C8 C9 112.92(13) . . ?
N3 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N3 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C8 107.24(13) . . ?
O1 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C3 N1 C2 115.28(13) . . ?
C3 N1 Cu01 106.34(10) . . ?
C2 N1 Cu01 110.47(10) . . ?
C3 N1 H1 107.9(17) . . ?
C2 N1 H1 107.2(16) . . ?
Cu01 N1 H1 109.6(17) . . ?
C5 N2 C4 116.26(13) . . ?
C5 N2 Cu01 108.56(10) . . ?
C4 N2 Cu01 109.51(10) . . ?
C5 N2 H2 108.1(15) . . ?
C4 N2 H2 107.4(15) . . ?
Cu01 N2 H2 106.6(16) . . ?
C8 N3 C7 116.14(14) . . ?
C8 N3 Cu01 109.56(10) . . ?
C7 N3 Cu01 107.12(10) . . ?
C8 N3 H3 107.5(14) . . ?
C7 N3 H3 105.9(14) . . ?
Cu01 N3 H3 110.5(15) . . ?
O4 N4 O3 122.78(13) . . ?
O4 N4 O2 119.69(14) . . ?
O3 N4 O2 117.52(13) . . ?
O7 N5 O6 120.67(16) . . ?
O7 N5 O5 120.30(15) . . ?
O6 N5 O5 119.03(14) . . ?
C1 O1 C9 114.87(13) . . ?
C1 O1 Cu01 105.20(8) . . ?
C9 O1 Cu01 106.23(9) . . ?
N4 O2 Cu01 102.11(9) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -51.09(18) . . . . ?
N1 C3 C4 N2 49.06(16) . . . . ?
N2 C5 C7 N3 -47.59(18) . . . . ?
N3 C8 C9 O1 52.96(19) . . . . ?
C4 C3 N1 C2 86.44(16) . . . . ?
C4 C3 N1 Cu01 -36.34(14) . . . . ?
C1 C2 N1 C3 -92.40(17) . . . . ?
C1 C2 N1 Cu01 28.16(17) . . . . ?
N2 Cu01 N1 C3 12.42(10) . . . . ?
N3 Cu01 N1 C3 83.56(19) . . . . ?
O2 Cu01 N1 C3 -141.02(10) . . . . ?
O1 Cu01 N1 C3 124.08(10) . . . . ?
N2 Cu01 N1 C2 -113.34(11) . . . . ?
N3 Cu01 N1 C2 -42.2(2) . . . . ?
O2 Cu01 N1 C2 93.22(11) . . . . ?
O1 Cu01 N1 C2 -1.68(11) . . . . ?
C7 C5 N2 C4 163.85(13) . . . . ?
C7 C5 N2 Cu01 39.90(15) . . . . ?
C3 C4 N2 C5 -160.13(13) . . . . ?
C3 C4 N2 Cu01 -36.68(14) . . . . ?
N3 Cu01 N2 C5 -18.76(10) . . . . ?
N1 Cu01 N2 C5 141.75(10) . . . . ?
O2 Cu01 N2 C5 -113.45(13) . . . . ?
O1 Cu01 N2 C5 61.71(11) . . . . ?
N3 Cu01 N2 C4 -146.64(10) . . . . ?
N1 Cu01 N2 C4 13.87(10) . . . . ?
O2 Cu01 N2 C4 118.67(12) . . . . ?
O1 Cu01 N2 C4 -66.17(11) . . . . ?
C9 C8 N3 C7 86.32(18) . . . . ?
C9 C8 N3 Cu01 -35.16(17) . . . . ?
C5 C7 N3 C8 -91.74(17) . . . . ?
C5 C7 N3 Cu01 31.04(16) . . . . ?
N2 Cu01 N3 C8 119.97(11) . . . . ?
N1 Cu01 N3 C8 48.9(2) . . . . ?
O2 Cu01 N3 C8 -87.17(11) . . . . ?
O1 Cu01 N3 C8 8.37(11) . . . . ?
N2 Cu01 N3 C7 -6.80(10) . . . . ?
N1 Cu01 N3 C7 -77.91(19) . . . . ?
O2 Cu01 N3 C7 146.06(10) . . . . ?
O1 Cu01 N3 C7 -118.40(11) . . . . ?
C2 C1 O1 C9 161.49(13) . . . . ?
C2 C1 O1 Cu01 45.06(14) . . . . ?
C8 C9 O1 C1 -157.17(13) . . . . ?
C8 C9 O1 Cu01 -41.33(14) . . . . ?
N2 Cu01 O1 C1 58.03(11) . . . . ?
N3 Cu01 O1 C1 141.53(11) . . . . ?
N1 Cu01 O1 C1 -25.13(10) . . . . ?
O2 Cu01 O1 C1 -124.19(10) . . . . ?
N2 Cu01 O1 C9 -64.17(11) . . . . ?
N3 Cu01 O1 C9 19.32(10) . . . . ?
N1 Cu01 O1 C9 -147.34(11) . . . . ?
O2 Cu01 O1 C9 113.61(10) . . . . ?
O4 N4 O2 Cu01 170.62(13) . . . . ?
O3 N4 O2 Cu01 -8.66(16) . . . . ?
N2 Cu01 O2 N4 -5.84(17) . . . . ?
N3 Cu01 O2 N4 -98.52(10) . . . . ?
N1 Cu01 O2 N4 95.84(10) . . . . ?
O1 Cu01 O2 N4 178.71(9) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.080