# Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 186/1689

data_isof 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C25 H25 Cu2 N3 O6' 
_chemical_formula_weight          '590.56' 
_chemical_melting_point           ? 
_chemical_compound_source         'Synthesis' 
 
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            Monoclinic 
_symmetry_space_group_name_H-M    'P21/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                    8.703(3) 
_cell_length_b                    14.442(3) 
_cell_length_c                    18.168(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.21(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      2280.0(18) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     294(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       16 
_cell_measurement_theta_max       32 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             'green block' 
_exptl_crystal_size_max           0.3 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.13 
_exptl_crystal_density_meas       'not measured '
_exptl_crystal_density_diffrn     1.720 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1208 
_exptl_absorpt_coefficient_mu     2.728 
_exptl_absorpt_correction_type    DIFABS 
_exptl_absorpt_correction_T_min   0.586 
_exptl_absorpt_correction_T_max   1.000 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       294(2) 
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   ? 
_diffrn_measurement_device        'Enraf-Nonius CAD4' 
_diffrn_measurement_method        '\w-2theta' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   3600 
_diffrn_standards_decay_%         <1 
_diffrn_reflns_number             4675 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0646 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          3.91 
_diffrn_reflns_theta_max          74.89 
_reflns_number_total              4675 
_reflns_number_observed           2921 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'ENRAF-NONIUS CAD4 (1989)' 
_computing_cell_refinement        'ENRAF-NONIUS CAD4 (1989)' 
_computing_data_reduction         'LOCAL PROGRAM' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'ZORTEP (Zsolnai, 1997)' 
_computing_publication_material   'SHELXL-93; PARST (Nardelli, 1995)' 

_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 18 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+4.8424P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      patterson
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4657 
_refine_ls_number_parameters      325 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1139 
_refine_ls_R_factor_obs           0.0633 
_refine_ls_wR_factor_all          0.2157 
_refine_ls_wR_factor_obs          0.1613 
_refine_ls_goodness_of_fit_all    1.005 
_refine_ls_goodness_of_fit_obs    0.984 
_refine_ls_restrained_S_all       1.030 
_refine_ls_restrained_S_obs       0.984 
_refine_ls_shift/esd_max          0.865 
_refine_ls_shift/esd_mean         0.560 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Cu1 Cu 0.70270(11) 0.01639(6) 0.16750(6) 0.0415(3) Uani 1 d . . 
Cu2 Cu 0.68440(12) 0.02655(7) 0.35885(6) 0.0468(3) Uani 1 d . . 
O2 O 0.7720(5) -0.0184(3) 0.0736(3) 0.0481(12) Uani 1 d . . 
O1 O 0.6139(5) 0.0489(3) 0.2591(3) 0.0437(11) Uani 1 d . . 
O3 O 0.7752(7) 0.0261(4) 0.4564(4) 0.067(2) Uani 1 d . . 
O4 O 0.8228(7) -0.0725(4) 0.3334(4) 0.068(2) Uani 1 d . . 
O5 O 0.8053(7) -0.0949(4) 0.2111(3) 0.0605(15) Uani 1 d . . 
N1 N 0.5443(6) 0.0996(4) 0.1248(3) 0.0394(13) Uani 1 d . . 
N2 N 0.5235(7) 0.1113(4) 0.3830(3) 0.0455(14) Uani 1 d . . 
C1 C 0.7407(7) 0.0248(5) 0.0104(4) 0.0407(15) Uani 1 d . . 
C2 C 0.8294(9) 0.0048(6) -0.0500(5) 0.055(2) Uani 1 d . . 
H2 H 0.9065(9) -0.0397(6) -0.0449(5) 0.066 Uiso 1 calc R . 
C3 C 0.8047(10) 0.0496(7) -0.1165(5) 0.063(2) Uani 1 d . . 
H3 H 0.8686(10) 0.0368(7) -0.1546(5) 0.075 Uiso 1 calc R . 
C4 C 0.6869(11) 0.1132(7) -0.1280(5) 0.064(2) Uani 1 d . . 
H4 H 0.6699(11) 0.1421(7) -0.1735(5) 0.077 Uiso 1 calc R . 
C5 C 0.5968(10) 0.1323(5) -0.0713(5) 0.057(2) Uani 1 d . . 
H5 H 0.5161(10) 0.1740(5) -0.0792(5) 0.068 Uiso 1 calc R . 
C6 C 0.6206(8) 0.0916(4) -0.0010(4) 0.041(2) Uani 1 d . . 
C7 C 0.5230(8) 0.1206(4) 0.0566(4) 0.042(2) Uani 1 d . . 
H7 H 0.4384(8) 0.1573(4) 0.0431(4) 0.050 Uiso 1 calc R . 
C8 C 0.4415(8) 0.1333(5) 0.1784(4) 0.044(2) Uani 1 d . . 
H8A H 0.3519(8) 0.0935(5) 0.1798(4) 0.053 Uiso 1 calc R . 
H8B H 0.4073(8) 0.1955(5) 0.1658(4) 0.053 Uiso 1 calc R . 
C9 C 0.5299(9) 0.1330(5) 0.2524(4) 0.051(2) Uani 1 d . . 
H9 H 0.6034(9) 0.1845(5) 0.2536(4) 0.061 Uiso 1 calc R . 
C10 C 0.4310(9) 0.1427(5) 0.3168(4) 0.045(2) Uani 1 d . . 
H10A H 0.4003(9) 0.2068(5) 0.3225(4) 0.054 Uiso 1 calc R . 
H10B H 0.3391(9) 0.1051(5) 0.3095(4) 0.054 Uiso 1 calc R . 
C11 C 0.4851(10) 0.1320(5) 0.4477(4) 0.051(2) Uani 1 d . . 
H11 H 0.3954(10) 0.1661(5) 0.4518(4) 0.061 Uiso 1 calc R . 
C12 C 0.5707(10) 0.1065(5) 0.5151(5) 0.057(2) Uani 1 d . . 
C13 C 0.5115(13) 0.1351(5) 0.5819(5) 0.068(3) Uani 1 d . . 
H13 H 0.4170(13) 0.1653(5) 0.5810(5) 0.082 Uiso 1 calc R . 
C14 C 0.5908(16) 0.1194(6) 0.6491(5) 0.086(4) Uani 1 d . . 
H14 H 0.5501(16) 0.1379(6) 0.6930(5) 0.103 Uiso 1 calc R . 
C15 C 0.7350(16) 0.0744(8) 0.6492(6) 0.095(4) Uani 1 d . . 
H15 H 0.7897(16) 0.0638(8) 0.6938(6) 0.114 Uiso 1 calc R . 
C16 C 0.7957(13) 0.0463(7) 0.5852(7) 0.088(4) Uani 1 d . . 
H16 H 0.8921(13) 0.0182(7) 0.5868(7) 0.106 Uiso 1 calc R . 
C17 C 0.7129(11) 0.0593(5) 0.5158(5) 0.065(3) Uani 1 d . . 
C18 C 0.8431(8) -0.1170(5) 0.2759(6) 0.055(2) Uani 1 d . . 
C19 C 0.9271(8) -0.2081(5) 0.2861(5) 0.051(2) Uani 1 d . . 
C20 C 0.9811(9) -0.2357(5) 0.3557(6) 0.060(2) Uani 1 d . . 
H20 H 0.9617(9) -0.2004(5) 0.3970(6) 0.072 Uiso 1 calc R . 
C21 C 1.0651(10) -0.3174(6) 0.3626(6) 0.065(2) Uani 1 d . . 
H21 H 1.1035(10) -0.3344(6) 0.4095(6) 0.077 Uiso 1 calc R . 
C22 C 1.0361(11) -0.3471(6) 0.2411(6) 0.068(3) Uani 1 d . . 
H22 H 1.0505(11) -0.3862(6) 0.2013(6) 0.082 Uiso 1 calc R . 
C23 C 0.9541(10) -0.2646(6) 0.2277(6) 0.066(2) Uani 1 d . . 
H23 H 0.9187(10) -0.2486(6) 0.1801(6) 0.079 Uiso 1 calc R . 
N3  N 1.0942(8) -0.3727(4) 0.3069(4) 0.056(2) Uani 1 d . . 
O6  O 0.7936(10) -0.2893(6) 0.5487(5) 0.100(2) Uani 1 d . . 
c24 C 0.9508(12) -0.1265(7) 0.5298(6) 0.099(3) Uani 1 d . . 
c25 C 0.9525(13) -0.2513(8) 0.5420(6) 0.134(3) Uani 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 0.0361(5) 0.0298(5) 0.0576(7) -0.0008(4) -0.0046(4) 0.0081(4) 
Cu2 0.0441(6) 0.0314(5) 0.0622(7) -0.0020(5) -0.0202(5) 0.0090(4) 
O2 0.039(3) 0.040(3) 0.065(3) -0.010(2) 0.000(2) 0.010(2) 
O1 0.043(3) 0.028(2) 0.059(3) -0.001(2) -0.008(2) 0.011(2) 
O3 0.063(4) 0.052(3) 0.082(4) 0.000(3) -0.035(3) 0.005(3) 
O4 0.061(4) 0.046(3) 0.094(5) -0.004(3) -0.021(3) 0.025(3) 
O5 0.068(4) 0.038(3) 0.074(4) 0.004(3) -0.001(3) 0.020(3) 
N1 0.037(3) 0.029(3) 0.052(3) -0.005(2) -0.001(2) 0.004(2) 
N2 0.049(3) 0.037(3) 0.048(4) -0.001(3) -0.017(3) 0.003(3) 
C1 0.032(3) 0.033(3) 0.056(4) -0.012(3) -0.005(3) 0.001(3) 
C2 0.045(4) 0.058(5) 0.061(5) -0.023(4) -0.009(3) 0.004(3) 
C3 0.053(5) 0.078(6) 0.058(5) -0.018(5) 0.009(4) -0.009(4) 
C4 0.078(6) 0.069(6) 0.046(5) -0.004(4) 0.004(4) 0.002(5) 
C5 0.061(5) 0.045(4) 0.063(5) -0.003(4) 0.000(4) 0.005(4) 
C6 0.042(4) 0.028(3) 0.053(4) -0.007(3) 0.001(3) -0.003(3) 
C7 0.041(4) 0.031(3) 0.053(4) -0.005(3) -0.005(3) 0.004(3) 
C8 0.037(4) 0.043(4) 0.052(4) -0.002(3) -0.004(3) 0.013(3) 
C9 0.047(4) 0.042(4) 0.060(5) -0.001(3) -0.015(4) 0.012(3) 
C10 0.049(4) 0.041(3) 0.043(4) -0.006(3) -0.010(3) 0.013(3) 
C11 0.069(5) 0.028(3) 0.053(4) -0.007(3) -0.017(4) 0.010(3) 
C12 0.081(6) 0.028(3) 0.058(5) 0.001(3) -0.029(4) -0.009(3) 
C13 0.115(8) 0.035(4) 0.051(5) -0.002(3) -0.017(5) -0.013(4) 
C14 0.158(11) 0.049(5) 0.047(5) 0.010(4) -0.031(6) -0.035(6) 
C15 0.143(11) 0.066(6) 0.069(7) 0.030(5) -0.061(7) -0.042(7) 
C16 0.087(7) 0.073(6) 0.097(8) 0.025(6) -0.058(7) -0.022(5) 
C17 0.080(6) 0.036(4) 0.074(6) 0.004(4) -0.042(5) -0.010(4) 
C18 0.034(4) 0.030(3) 0.101(7) 0.011(4) -0.009(4) 0.006(3) 
C19 0.029(3) 0.030(3) 0.094(6) 0.010(4) -0.007(4) 0.001(3) 
C20 0.045(4) 0.039(4) 0.095(7) 0.002(4) -0.001(4) 0.012(3) 
C21 0.057(5) 0.045(4) 0.090(7) 0.015(4) -0.005(5) 0.018(4) 
C22 0.062(6) 0.048(5) 0.092(7) -0.006(5) -0.011(5) 0.019(4) 
C23 0.058(5) 0.050(5) 0.088(6) 0.007(4) -0.018(5) 0.021(4) 
N3  0.051(4) 0.038(3) 0.078(5) 0.006(3) -0.004(3) 0.015(3) 
O6  0.090(6) 0.045(6) 0.167(6) 0.016(5) 0.022(5) 0.009(5) 
c24 0.097(6) 0.081(6) 0.117(6) 0.004(5) 0.000(5) -0.002(5) 
c25 0.153(7) 0.124(7) 0.126(7) 0.007(6) 0.011(6) 0.007(6) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cu1 O2 1.909(5) . ? 
Cu1 O1 1.932(5) . ? 
Cu1 N1 1.956(5) . ? 
Cu1 O5 1.983(5) . ? 
Cu1 N3 2.411(6) 2_755 ? 
Cu1 Cu2 3.492(3) . ? 
Cu2 O3 1.899(6) . ? 
Cu2 O1 1.908(5) . ? 
Cu2 N2 1.929(6) . ? 
Cu2 O4 1.942(6) . ? 
O2 C1 1.321(9) . ? 
O1 C9 1.419(8) . ? 
O3 C17 1.324(12) . ? 
O4 C18 1.248(11) . ? 
O5 C18 1.245(11) . ? 
N1 C7 1.278(9) . ? 
N1 C8 1.444(9) . ? 
N2 C11 1.275(10) . ? 
N2 C10 1.480(8) . ? 
C1 C2 1.406(11) . ? 
C1 C6 1.429(9) . ? 
C2 C3 1.376(12) . ? 
C3 C4 1.383(13) . ? 
C4 C5 1.357(12) . ? 
C5 C6 1.411(11) . ? 
C6 C7 1.446(10) . ? 
C8 C9 1.511(10) . ? 
C9 C10 1.497(11) . ? 
C11 C12 1.444(10) . ? 
C12 C13 1.408(12) . ? 
C12 C17 1.412(13) . ? 
C13 C14 1.388(12) . ? 
C14 C15 1.41(2) . ? 
C15 C16 1.37(2) . ? 
C16 C17 1.430(12) . ? 
C18 C19 1.511(9) . ? 
C19 C23 1.369(12) . ? 
C19 C20 1.384(12) . ? 
C20 C21 1.390(10) . ? 
C21 N3 1.324(11) . ? 
C22 N3 1.325(11) . ? 
C22 C23 1.404(10) . ? 
N3  Cu1 2.411(6) 2_745 ? 
O6  c25 1.499(13) . ? 
c24 c25 1.82(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 
O2 Cu1 O1 174.8(2) . . ? 
O2 Cu1 N1 93.3(2) . . ? 
O1 Cu1 N1 83.4(2) . . ? 
O2 Cu1 O5 89.2(2) . . ? 
O1 Cu1 O5 92.6(2) . . ? 
N1 Cu1 O5 161.5(2) . . ? 
O2 Cu1 N3 94.7(2) . 2_755 ? 
O1 Cu1 N3 89.8(2) . 2_755 ? 
N1 Cu1 N3 99.3(2) . 2_755 ? 
O5 Cu1 N3 98.8(2) . 2_755 ? 
O2 Cu1 Cu2 159.3(2) . . ? 
O1 Cu1 Cu2 24.40(13) . . ? 
N1 Cu1 Cu2 107.4(2) . . ? 
O5 Cu1 Cu2 71.4(2) . . ? 
N3 Cu1 Cu2 81.6(2) 2_755 . ? 
O3 Cu2 O1 169.0(2) . . ? 
O3 Cu2 N2 93.4(3) . . ? 
O1 Cu2 N2 84.8(2) . . ? 
O3 Cu2 O4 89.3(3) . . ? 
O1 Cu2 O4 94.0(2) . . ? 
N2 Cu2 O4 171.6(3) . . ? 
O3 Cu2 Cu1 152.7(2) . . ? 
O1 Cu2 Cu1 24.74(14) . . ? 
N2 Cu2 Cu1 109.1(2) . . ? 
O4 Cu2 Cu1 70.6(2) . . ? 
C1 O2 Cu1 126.4(4) . . ? 
C9 O1 Cu2 111.3(4) . . ? 
C9 O1 Cu1 111.3(4) . . ? 
Cu2 O1 Cu1 130.9(2) . . ? 
C17 O3 Cu2 126.2(5) . . ? 
C18 O4 Cu2 134.3(5) . . ? 
C18 O5 Cu1 132.4(5) . . ? 
C7 N1 C8 120.8(6) . . ? 
C7 N1 Cu1 126.2(5) . . ? 
C8 N1 Cu1 112.9(4) . . ? 
C11 N2 C10 121.2(6) . . ? 
C11 N2 Cu2 126.1(5) . . ? 
C10 N2 Cu2 112.3(5) . . ? 
O2 C1 C2 119.1(6) . . ? 
O2 C1 C6 123.9(6) . . ? 
C2 C1 C6 117.1(7) . . ? 
C3 C2 C1 121.5(8) . . ? 
C2 C3 C4 121.5(8) . . ? 
C5 C4 C3 118.4(9) . . ? 
C4 C5 C6 122.7(8) . . ? 
C5 C6 C1 118.7(7) . . ? 
C5 C6 C7 118.2(7) . . ? 
C1 C6 C7 123.0(7) . . ? 
N1 C7 C6 125.0(6) . . ? 
N1 C8 C9 107.2(6) . . ? 
O1 C9 C10 109.2(6) . . ? 
O1 C9 C8 108.2(6) . . ? 
C10 C9 C8 114.1(6) . . ? 
N2 C10 C9 107.2(6) . . ? 
N2 C11 C12 124.9(8) . . ? 
C13 C12 C17 119.8(8) . . ? 
C13 C12 C11 117.4(8) . . ? 
C17 C12 C11 122.7(8) . . ? 
C14 C13 C12 121.5(10) . . ? 
C13 C14 C15 118.3(11) . . ? 
C16 C15 C14 121.5(9) . . ? 
C15 C16 C17 120.8(11) . . ? 
O3 C17 C12 124.5(7) . . ? 
O3 C17 C16 117.5(10) . . ? 
C12 C17 C16 118.0(10) . . ? 
O5 C18 O4 128.1(7) . . ? 
O5 C18 C19 116.1(8) . . ? 
O4 C18 C19 115.8(8) . . ? 
C23 C19 C20 118.2(7) . . ? 
C23 C19 C18 121.7(8) . . ? 
C20 C19 C18 120.0(8) . . ? 
C21 C20 C19 118.5(9) . . ? 
N3 C21 C20 124.4(9) . . ? 
N3 C22 C23 123.9(9) . . ? 
C19 C23 C22 118.6(9) . . ? 
C22 N3 C21 116.2(7) . . ? 
C22 N3 Cu1 126.7(6) . 2_745 ? 
C21 N3 Cu1 115.0(5) . 2_745 ? 
O6 c25 c24 111.8(8) . . ? 
 
_refine_diff_density_max    0.628 
_refine_diff_density_min   -0.542 
_refine_diff_density_rms    0.086