# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 186/2318 data_olga2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Cu N4 O10' _chemical_formula_weight 678.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0020 0.0020 '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' 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.2630 1.2660 '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 8.9105(14) _cell_length_b 10.2444(16) _cell_length_c 10.4369(17) _cell_angle_alpha 63.643(17) _cell_angle_beta 65.680(18) _cell_angle_gamma 75.792(18) _cell_volume 775.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle ' _exptl_crystal_colour ' blue' _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 355 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4439 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 23.00 _reflns_number_total 2044 _reflns_number_gt 1817 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _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 w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 2044 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 0.787 _refine_ls_restrained_S_all 0.787 _refine_ls_shift/su_max 0.005 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.01958(19) Uani 1 d S . . N1 N 0.1252(2) 0.1326(2) 0.0085(2) 0.0218(5) Uani 1 d . . . N2 N 0.4308(2) -0.2132(2) -0.4008(2) 0.0231(5) Uani 1 d . . . O1 O 0.0412(2) 0.12153(18) -0.22468(19) 0.0257(4) Uani 1 d . . . O2 O 0.2377(2) -0.13073(18) -0.07307(18) 0.0274(4) Uani 1 d . . . O3 O 0.3320(2) -0.0303(2) -0.5861(2) 0.0391(5) Uani 1 d . . . O4 O 0.6015(3) -0.4135(2) -0.4025(2) 0.0455(5) Uani 1 d . . . O5 O 0.7001(3) -0.5686(3) -0.1312(3) 0.0549(6) Uani 1 d . . . H16 H 0.691(5) -0.526(4) -0.229(5) 0.066 Uiso 1 d . . . H17 H 0.698(4) -0.660(5) -0.109(4) 0.066 Uiso 1 d . . . C1 C 0.2472(3) 0.0773(3) 0.0647(3) 0.0304(6) Uani 1 d . . . H1 H 0.2707 -0.0246 0.1026 0.036 Uiso 1 calc R . . C2 C 0.3407(4) 0.1633(3) 0.0697(3) 0.0368(7) Uani 1 d . . . H2 H 0.4269 0.1207 0.1090 0.044 Uiso 1 calc R . . C3 C 0.3055(3) 0.3122(3) 0.0161(3) 0.0350(7) Uani 1 d . . . H3 H 0.3664 0.3733 0.0190 0.042 Uiso 1 calc R . . C4 C 0.1794(3) 0.3699(3) -0.0418(3) 0.0331(7) Uani 1 d . . . H4 H 0.1528 0.4714 -0.0788 0.040 Uiso 1 calc R . . C5 C 0.0921(3) 0.2782(3) -0.0454(3) 0.0264(6) Uani 1 d . . . H5 H 0.0073 0.3186 -0.0867 0.032 Uiso 1 calc R . . C6 C -0.0829(4) 0.3824(3) -0.6199(4) 0.0484(8) Uani 1 d . . . H6A H -0.1711 0.4583 -0.6084 0.058 Uiso 1 calc R . . H6B H -0.1148 0.3168 -0.6470 0.058 Uiso 1 calc R . . H6C H 0.0168 0.4265 -0.6996 0.058 Uiso 1 calc R . . C7 C -0.0513(4) 0.2973(3) -0.4709(3) 0.0461(8) Uani 1 d . . . H7A H -0.1530 0.2545 -0.3902 0.055 Uiso 1 calc R . . H7B H -0.0209 0.3640 -0.4430 0.055 Uiso 1 calc R . . C8 C 0.0834(3) 0.1784(3) -0.4822(3) 0.0297(6) Uani 1 d . . . H8A H 0.1848 0.2224 -0.5622 0.036 Uiso 1 calc R . . H8B H 0.0536 0.1144 -0.5139 0.036 Uiso 1 calc R . . C9 C 0.1189(3) 0.0866(3) -0.3370(3) 0.0225(5) Uani 1 d . . . C10 C 0.2377(3) -0.0376(2) -0.3298(3) 0.0219(6) Uani 1 d . . . C11 C 0.2843(3) -0.1316(2) -0.2030(3) 0.0218(6) Uani 1 d . . . C12 C 0.4113(3) -0.2478(3) -0.2440(3) 0.0246(6) Uani 1 d . . . H12A H 0.5159 -0.2434 -0.2365 0.030 Uiso 1 calc R . . H12B H 0.3722 -0.3455 -0.1770 0.030 Uiso 1 calc R . . C13 C 0.3309(3) -0.0843(3) -0.4564(3) 0.0249(6) Uani 1 d . . . C14 C 0.5293(3) -0.3059(3) -0.4725(3) 0.0295(6) Uani 1 d . . . C15 C 0.5439(4) -0.2722(3) -0.6314(3) 0.0388(7) Uani 1 d . . . H15A H 0.6165 -0.3473 -0.6650 0.047 Uiso 1 calc R . . H15B H 0.5892 -0.1782 -0.6985 0.047 Uiso 1 calc R . . H15C H 0.4356 -0.2693 -0.6342 0.047 Uiso 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 0.0230(3) 0.0186(3) 0.0177(3) -0.00606(19) -0.00842(19) -0.00216(17) N1 0.0253(10) 0.0214(11) 0.0186(10) -0.0065(8) -0.0097(9) -0.0003(8) N2 0.0258(11) 0.0218(10) 0.0204(10) -0.0079(9) -0.0090(9) 0.0014(9) O1 0.0276(9) 0.0242(9) 0.0251(9) -0.0104(8) -0.0092(8) 0.0000(7) O2 0.0333(9) 0.0292(9) 0.0201(9) -0.0090(8) -0.0097(8) -0.0033(7) O3 0.0544(12) 0.0373(11) 0.0212(11) -0.0119(9) -0.0181(9) 0.0138(9) O4 0.0558(13) 0.0395(12) 0.0446(12) -0.0224(10) -0.0263(11) 0.0185(10) O5 0.0770(16) 0.0406(13) 0.0526(14) -0.0141(11) -0.0327(13) -0.0032(12) C1 0.0376(14) 0.0250(13) 0.0310(14) -0.0081(11) -0.0178(12) -0.0014(11) C2 0.0431(16) 0.0378(16) 0.0390(16) -0.0100(13) -0.0266(14) -0.0061(13) C3 0.0467(16) 0.0334(15) 0.0350(15) -0.0110(13) -0.0216(13) -0.0113(12) C4 0.0404(15) 0.0215(13) 0.0362(15) -0.0097(12) -0.0124(13) -0.0053(12) C5 0.0267(13) 0.0234(13) 0.0272(14) -0.0070(11) -0.0117(11) 0.0000(10) C6 0.0445(17) 0.0430(17) 0.0431(18) -0.0071(15) -0.0206(15) 0.0114(14) C7 0.0458(17) 0.0450(18) 0.0363(17) -0.0133(14) -0.0163(14) 0.0137(14) C8 0.0334(14) 0.0269(14) 0.0278(14) -0.0099(12) -0.0134(12) 0.0025(11) C9 0.0207(12) 0.0241(12) 0.0220(13) -0.0072(11) -0.0053(11) -0.0078(10) C10 0.0242(12) 0.0207(12) 0.0209(13) -0.0057(11) -0.0091(11) -0.0041(10) C11 0.0223(12) 0.0215(12) 0.0215(13) -0.0061(11) -0.0059(10) -0.0089(10) C12 0.0288(13) 0.0223(12) 0.0211(13) -0.0043(11) -0.0122(11) -0.0013(10) C13 0.0269(12) 0.0244(13) 0.0229(14) -0.0085(11) -0.0083(11) -0.0030(10) C14 0.0288(13) 0.0273(14) 0.0331(15) -0.0131(12) -0.0093(12) -0.0031(11) C15 0.0395(15) 0.0455(17) 0.0365(16) -0.0269(14) -0.0112(13) 0.0061(13) _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 2.0073(19) . ? Cu1 N1 2.0073(19) 2 ? Cu1 O1 2.0265(18) 2 ? Cu1 O1 2.0265(18) . ? Cu1 O2 2.2461(18) . ? N1 C1 1.332(3) . ? N1 C5 1.343(3) . ? N2 C14 1.383(3) . ? N2 C13 1.429(3) . ? N2 C12 1.454(3) . ? O1 C9 1.251(3) . ? O2 C11 1.248(3) . ? O3 C13 1.210(3) . ? O4 C14 1.220(3) . ? C1 C2 1.382(4) . ? C2 C3 1.375(4) . ? C3 C4 1.377(4) . ? C4 C5 1.380(4) . ? C6 C7 1.514(4) . ? C7 C8 1.494(4) . ? C8 C9 1.505(4) . ? C9 C10 1.436(3) . ? C10 C11 1.406(4) . ? C10 C13 1.458(3) . ? C11 C12 1.508(3) . ? C14 C15 1.490(4) . ? 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 N1 180.0 . 2 ? N1 Cu1 O1 88.97(7) . 2 ? N1 Cu1 O1 91.03(7) 2 2 ? N1 Cu1 O1 91.03(7) . . ? N1 Cu1 O1 88.97(7) 2 . ? O1 Cu1 O1 180.0 2 . ? N1 Cu1 O2 89.63(7) . . ? N1 Cu1 O2 90.37(7) 2 . ? O1 Cu1 O2 92.98(7) 2 . ? O1 Cu1 O2 87.02(7) . . ? C1 N1 C5 118.4(2) . . ? C1 N1 Cu1 120.16(16) . . ? C5 N1 Cu1 121.47(17) . . ? C14 N2 C13 128.8(2) . . ? C14 N2 C12 120.0(2) . . ? C13 N2 C12 111.12(18) . . ? C9 O1 Cu1 129.59(16) . . ? C11 O2 Cu1 117.20(16) . . ? N1 C1 C2 122.8(2) . . ? C3 C2 C1 118.8(3) . . ? C4 C3 C2 118.6(2) . . ? C3 C4 C5 119.7(2) . . ? N1 C5 C4 121.7(2) . . ? C6 C7 C8 111.7(3) . . ? C7 C8 C9 114.7(2) . . ? O1 C9 C10 122.0(2) . . ? O1 C9 C8 117.9(2) . . ? C10 C9 C8 120.1(2) . . ? C11 C10 C9 126.3(2) . . ? C11 C10 C13 109.3(2) . . ? C9 C10 C13 124.4(2) . . ? O2 C11 C10 130.7(2) . . ? O2 C11 C12 120.3(2) . . ? C10 C11 C12 108.9(2) . . ? N2 C12 C11 103.9(2) . . ? O3 C13 N2 123.2(2) . . ? O3 C13 C10 130.2(2) . . ? N2 C13 C10 106.7(2) . . ? O4 C14 N2 118.3(2) . . ? O4 C14 C15 122.1(2) . . ? N2 C14 C15 119.6(2) . . ? 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 N1 Cu1 N1 C1 168(100) 2 . . . ? O1 Cu1 N1 C1 52.42(18) 2 . . . ? O1 Cu1 N1 C1 -127.58(18) . . . . ? O2 Cu1 N1 C1 -40.57(18) . . . . ? N1 Cu1 N1 C5 -13(100) 2 . . . ? O1 Cu1 N1 C5 -129.43(18) 2 . . . ? O1 Cu1 N1 C5 50.57(18) . . . . ? O2 Cu1 N1 C5 137.58(18) . . . . ? N1 Cu1 O1 C9 117.40(19) . . . . ? N1 Cu1 O1 C9 -62.60(19) 2 . . . ? O1 Cu1 O1 C9 162(100) 2 . . . ? O2 Cu1 O1 C9 27.83(19) . . . . ? N1 Cu1 O2 C11 -115.68(16) . . . . ? N1 Cu1 O2 C11 64.32(16) 2 . . . ? O1 Cu1 O2 C11 155.37(15) 2 . . . ? O1 Cu1 O2 C11 -24.63(15) . . . . ? C5 N1 C1 C2 0.0(4) . . . . ? Cu1 N1 C1 C2 178.2(2) . . . . ? N1 C1 C2 C3 0.8(4) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C1 N1 C5 C4 -0.9(3) . . . . ? Cu1 N1 C5 C4 -179.06(18) . . . . ? C3 C4 C5 N1 1.0(4) . . . . ? C6 C7 C8 C9 -178.6(2) . . . . ? Cu1 O1 C9 C10 -19.8(3) . . . . ? Cu1 O1 C9 C8 159.64(16) . . . . ? C7 C8 C9 O1 -3.7(3) . . . . ? C7 C8 C9 C10 175.7(2) . . . . ? O1 C9 C10 C11 -1.4(3) . . . . ? C8 C9 C10 C11 179.2(2) . . . . ? O1 C9 C10 C13 179.5(2) . . . . ? C8 C9 C10 C13 0.1(3) . . . . ? Cu1 O2 C11 C10 17.7(3) . . . . ? Cu1 O2 C11 C12 -162.08(15) . . . . ? C9 C10 C11 O2 -0.2(4) . . . . ? C13 C10 C11 O2 179.1(2) . . . . ? C9 C10 C11 C12 179.7(2) . . . . ? C13 C10 C11 C12 -1.1(3) . . . . ? C14 N2 C12 C11 -174.49(19) . . . . ? C13 N2 C12 C11 2.1(2) . . . . ? O2 C11 C12 N2 179.31(19) . . . . ? C10 C11 C12 N2 -0.5(2) . . . . ? C14 N2 C13 O3 -7.2(4) . . . . ? C12 N2 C13 O3 176.6(2) . . . . ? C14 N2 C13 C10 173.4(2) . . . . ? C12 N2 C13 C10 -2.8(2) . . . . ? C11 C10 C13 O3 -176.9(2) . . . . ? C9 C10 C13 O3 2.3(4) . . . . ? C11 C10 C13 N2 2.4(2) . . . . ? C9 C10 C13 N2 -178.4(2) . . . . ? C13 N2 C14 O4 -177.9(2) . . . . ? C12 N2 C14 O4 -2.0(3) . . . . ? C13 N2 C14 C15 2.1(4) . . . . ? C12 N2 C14 C15 177.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.402 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.066