# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_311251 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33.22 H28.86 Cu2 N2 O8' _chemical_formula_weight 711.14 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 C2/c 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 18.468(3) _cell_length_b 9.7026(14) _cell_length_c 19.307(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.811(4) _cell_angle_gamma 90.00 _cell_volume 3418.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1457 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5107 _exptl_absorpt_correction_T_max 0.8602 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12330 _diffrn_reflns_av_R_equivalents 0.0922 _diffrn_reflns_av_sigmaI/netI 0.1071 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4223 _reflns_number_gt 1888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0527P)^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 4223 _refine_ls_number_parameters 223 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1455 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.885 _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 C1 C 0.1250(3) 0.7305(4) 0.2116(2) 0.0476(11) Uani 1 1 d . . . C2 C 0.1993(2) 0.7311(4) 0.1907(2) 0.0498(11) Uani 1 1 d . . . C3 C 0.2286(3) 0.8508(5) 0.1684(3) 0.0817(17) Uani 1 1 d . . . H3 H 0.2025 0.9328 0.1681 0.098 Uiso 1 1 calc R . . C4 C 0.2953(4) 0.8501(6) 0.1466(3) 0.101(2) Uani 1 1 d . . . H4 H 0.3146 0.9314 0.1317 0.122 Uiso 1 1 calc R . . C5 C 0.3341(3) 0.7289(7) 0.1467(3) 0.0983(19) Uani 1 1 d . . . H5 H 0.3788 0.7274 0.1302 0.118 Uiso 1 1 calc R . . C6 C 0.3069(3) 0.6126(6) 0.1707(3) 0.0861(19) Uani 1 1 d . . . H6 H 0.3340 0.5315 0.1723 0.103 Uiso 1 1 calc R . . C7 C 0.2398(3) 0.6125(4) 0.1929(3) 0.0663(15) Uani 1 1 d . . . H7 H 0.2218 0.5315 0.2096 0.080 Uiso 1 1 calc R . . C8 C 0.0634(2) 0.7214(5) 0.3766(2) 0.0536(11) Uani 1 1 d . . . C9 C 0.1025(3) 0.7190(5) 0.4491(2) 0.0613(12) Uani 1 1 d . . . C10 C 0.1374(3) 0.8322(6) 0.4787(3) 0.0895(19) Uani 1 1 d . . . H10 H 0.1360 0.9140 0.4534 0.107 Uiso 1 1 calc R . . C11 C 0.1751(4) 0.8269(7) 0.5462(4) 0.117(2) Uani 1 1 d . . . H11 H 0.1989 0.9052 0.5658 0.140 Uiso 1 1 calc R . . C12 C 0.1777(4) 0.7098(9) 0.5840(3) 0.114(2) Uani 1 1 d . . . H12 H 0.2033 0.7066 0.6294 0.137 Uiso 1 1 calc R . . C13 C 0.1425(4) 0.5966(7) 0.5546(3) 0.113(2) Uani 1 1 d . . . H13 H 0.1430 0.5158 0.5806 0.135 Uiso 1 1 calc R . . C14 C 0.1062(3) 0.5996(5) 0.4877(3) 0.0883(19) Uani 1 1 d . . . H14 H 0.0838 0.5201 0.4679 0.106 Uiso 1 1 calc R . . C15 C 0.0307(2) 1.1562(3) 0.2041(2) 0.0512(12) Uani 1 1 d . . . H15 H 0.0530 1.1096 0.1709 0.061 Uiso 1 1 calc R . . C16 C 0.0306(2) 0.2982(3) 0.2039(2) 0.0508(12) Uani 1 1 d . . . H16 H 0.0527 0.3451 0.1706 0.061 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85933(6) 0.2500 0.0485(3) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59262(6) 0.2500 0.0492(3) Uani 1 2 d S . . N1 N 0.0000 1.0842(4) 0.2500 0.0436(14) Uani 1 2 d S . . N2 N 0.0000 0.3692(4) 0.2500 0.0428(13) Uani 1 2 d S . . O1 O 0.09240(16) 0.8440(2) 0.21409(15) 0.0572(9) Uani 1 1 d . . . O2 O 0.09871(17) 0.6151(2) 0.22572(16) 0.0608(9) Uani 1 1 d . . . O3 O 0.05380(17) 0.8363(3) 0.34576(15) 0.0608(9) Uani 1 1 d . . . O4 O 0.04067(18) 0.6086(3) 0.34877(15) 0.0618(9) Uani 1 1 d . . . C1S C 0.0738(7) 0.8110(13) 0.0135(6) 0.187(9) Uani 0.608(13) 1 d PD . . H1S H 0.124(2) 0.811(14) 0.006(6) 0.281 Uiso 0.608(13) 1 d PD . . H2S H 0.059(7) 0.719(5) 0.024(6) 0.281 Uiso 0.608(13) 1 d PD . . H3S H 0.043(5) 0.844(13) -0.028(4) 0.281 Uiso 0.608(13) 1 d PD . . H4S H 0.069(7) 0.871(10) 0.052(4) 0.281 Uiso 0.608(13) 1 d PD . . 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 C1 0.062(3) 0.0277(17) 0.053(3) 0.0020(19) 0.008(2) 0.001(2) C2 0.047(3) 0.043(2) 0.059(3) -0.004(2) 0.008(2) 0.005(2) C3 0.069(4) 0.063(3) 0.120(5) 0.028(3) 0.036(4) 0.005(3) C4 0.072(5) 0.097(5) 0.145(6) 0.033(4) 0.048(4) 0.002(4) C5 0.049(4) 0.132(6) 0.118(5) -0.003(4) 0.028(4) 0.004(4) C6 0.055(4) 0.079(4) 0.120(5) -0.022(3) 0.002(4) 0.016(3) C7 0.057(4) 0.049(3) 0.090(4) -0.010(2) 0.004(3) 0.008(2) C8 0.063(3) 0.041(2) 0.057(3) -0.001(3) 0.011(3) -0.001(2) C9 0.067(3) 0.060(3) 0.057(3) -0.006(3) 0.009(3) -0.002(3) C10 0.119(6) 0.082(4) 0.063(4) -0.010(3) -0.001(4) -0.021(4) C11 0.144(7) 0.116(6) 0.081(5) -0.024(4) -0.011(5) -0.036(5) C12 0.118(6) 0.151(7) 0.066(4) -0.006(5) -0.009(4) 0.000(6) C13 0.143(7) 0.112(6) 0.075(5) 0.015(4) -0.007(5) 0.010(5) C14 0.117(6) 0.070(4) 0.072(4) 0.002(3) -0.004(4) 0.001(3) C15 0.069(3) 0.022(2) 0.067(3) -0.0016(19) 0.025(3) 0.0022(19) C16 0.068(3) 0.023(2) 0.069(3) 0.0064(18) 0.035(3) 0.0013(19) Cu1 0.0645(6) 0.0137(3) 0.0694(6) 0.000 0.0171(5) 0.000 Cu2 0.0695(7) 0.0135(3) 0.0648(6) 0.000 0.0109(5) 0.000 N1 0.055(4) 0.014(2) 0.063(4) 0.000 0.014(3) 0.000 N2 0.049(4) 0.019(2) 0.061(4) 0.000 0.013(3) 0.000 O1 0.066(2) 0.0259(15) 0.084(2) 0.0023(14) 0.0271(19) 0.0068(13) O2 0.072(3) 0.0260(15) 0.088(2) 0.0046(14) 0.024(2) 0.0021(14) O3 0.079(3) 0.0336(16) 0.069(2) -0.0008(14) 0.0094(19) -0.0072(15) O4 0.091(3) 0.0322(16) 0.059(2) 0.0014(13) 0.003(2) -0.0052(15) C1S 0.168(15) 0.26(2) 0.140(12) -0.011(12) 0.051(11) -0.069(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 C1 O1 1.259(4) . ? C1 O2 1.267(4) . ? C1 C2 1.488(6) . ? C2 C7 1.370(5) . ? C2 C3 1.378(6) . ? C3 C4 1.360(7) . ? C4 C5 1.377(7) . ? C5 C6 1.345(7) . ? C6 C7 1.371(6) . ? C8 O4 1.262(5) . ? C8 O3 1.264(5) . ? C8 C9 1.473(6) . ? C9 C10 1.356(6) . ? C9 C14 1.373(6) . ? C10 C11 1.380(7) . ? C11 C12 1.348(9) . ? C12 C13 1.356(8) . ? C13 C14 1.362(7) . ? C15 N1 1.323(4) . ? C15 C16 1.378(4) 1_565 ? C16 N2 1.319(4) . ? C16 C15 1.378(4) 1_545 ? Cu1 O1 1.943(3) 2 ? Cu1 O1 1.943(3) . ? Cu1 O3 1.973(3) . ? Cu1 O3 1.973(3) 2 ? Cu1 N1 2.182(4) . ? Cu1 Cu2 2.5878(8) . ? Cu2 O4 1.946(3) . ? Cu2 O4 1.946(3) 2 ? Cu2 O2 1.963(3) 2 ? Cu2 O2 1.963(3) . ? Cu2 N2 2.168(4) . ? N1 C15 1.323(4) 2 ? N2 C16 1.319(4) 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 O1 C1 O2 124.3(4) . . ? O1 C1 C2 118.2(4) . . ? O2 C1 C2 117.5(4) . . ? C7 C2 C3 118.6(4) . . ? C7 C2 C1 120.7(4) . . ? C3 C2 C1 120.7(4) . . ? C4 C3 C2 120.7(5) . . ? C3 C4 C5 119.9(5) . . ? C6 C5 C4 119.7(5) . . ? C5 C6 C7 120.7(5) . . ? C2 C7 C6 120.3(5) . . ? O4 C8 O3 123.4(4) . . ? O4 C8 C9 118.2(4) . . ? O3 C8 C9 118.3(4) . . ? C10 C9 C14 118.3(5) . . ? C10 C9 C8 121.3(5) . . ? C14 C9 C8 120.4(5) . . ? C9 C10 C11 120.4(6) . . ? C12 C11 C10 121.0(6) . . ? C11 C12 C13 118.7(6) . . ? C12 C13 C14 121.0(6) . . ? C13 C14 C9 120.6(5) . . ? N1 C15 C16 122.0(4) . 1_565 ? N2 C16 C15 121.4(4) . 1_545 ? O1 Cu1 O1 171.22(14) 2 . ? O1 Cu1 O3 90.04(13) 2 . ? O1 Cu1 O3 88.97(13) . . ? O1 Cu1 O3 88.97(13) 2 2 ? O1 Cu1 O3 90.04(13) . 2 ? O3 Cu1 O3 167.00(16) . 2 ? O1 Cu1 N1 94.39(7) 2 . ? O1 Cu1 N1 94.39(7) . . ? O3 Cu1 N1 96.50(8) . . ? O3 Cu1 N1 96.50(8) 2 . ? O1 Cu1 Cu2 85.61(7) 2 . ? O1 Cu1 Cu2 85.61(7) . . ? O3 Cu1 Cu2 83.50(8) . . ? O3 Cu1 Cu2 83.50(8) 2 . ? N1 Cu1 Cu2 180.000(1) . . ? O4 Cu2 O4 170.87(15) . 2 ? O4 Cu2 O2 89.45(13) . 2 ? O4 Cu2 O2 89.54(13) 2 2 ? O4 Cu2 O2 89.54(13) . . ? O4 Cu2 O2 89.45(13) 2 . ? O2 Cu2 O2 167.23(14) 2 . ? O4 Cu2 N2 94.57(7) . . ? O4 Cu2 N2 94.57(7) 2 . ? O2 Cu2 N2 96.38(7) 2 . ? O2 Cu2 N2 96.38(7) . . ? O4 Cu2 Cu1 85.43(7) . . ? O4 Cu2 Cu1 85.43(7) 2 . ? O2 Cu2 Cu1 83.62(7) 2 . ? O2 Cu2 Cu1 83.62(7) . . ? N2 Cu2 Cu1 180.0 . . ? C15 N1 C15 116.2(4) 2 . ? C15 N1 Cu1 121.9(2) 2 . ? C15 N1 Cu1 121.9(2) . . ? C16 N2 C16 117.1(4) 2 . ? C16 N2 Cu2 121.5(2) 2 . ? C16 N2 Cu2 121.5(2) . . ? C1 O1 Cu1 122.1(3) . . ? C1 O2 Cu2 123.4(3) . . ? C8 O3 Cu1 123.7(3) . . ? C8 O4 Cu2 122.7(3) . . ? 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 C7 174.3(4) . . . . ? O2 C1 C2 C7 -5.7(6) . . . . ? O1 C1 C2 C3 -6.0(6) . . . . ? O2 C1 C2 C3 174.0(4) . . . . ? C7 C2 C3 C4 2.3(8) . . . . ? C1 C2 C3 C4 -177.4(5) . . . . ? C2 C3 C4 C5 0.1(10) . . . . ? C3 C4 C5 C6 -2.5(10) . . . . ? C4 C5 C6 C7 2.3(10) . . . . ? C3 C2 C7 C6 -2.5(7) . . . . ? C1 C2 C7 C6 177.2(4) . . . . ? C5 C6 C7 C2 0.2(9) . . . . ? O4 C8 C9 C10 170.4(5) . . . . ? O3 C8 C9 C10 -10.1(7) . . . . ? O4 C8 C9 C14 -7.7(7) . . . . ? O3 C8 C9 C14 171.8(5) . . . . ? C14 C9 C10 C11 -0.5(9) . . . . ? C8 C9 C10 C11 -178.6(5) . . . . ? C9 C10 C11 C12 -0.3(10) . . . . ? C10 C11 C12 C13 -0.2(12) . . . . ? C11 C12 C13 C14 1.4(12) . . . . ? C12 C13 C14 C9 -2.2(10) . . . . ? C10 C9 C14 C13 1.7(9) . . . . ? C8 C9 C14 C13 179.8(5) . . . . ? O1 Cu1 Cu2 O4 -82.99(13) 2 . . . ? O1 Cu1 Cu2 O4 97.01(13) . . . . ? O3 Cu1 Cu2 O4 7.56(13) . . . . ? O3 Cu1 Cu2 O4 -172.44(13) 2 . . . ? N1 Cu1 Cu2 O4 76(100) . . . . ? O1 Cu1 Cu2 O4 97.01(13) 2 . . 2 ? O1 Cu1 Cu2 O4 -82.99(13) . . . 2 ? O3 Cu1 Cu2 O4 -172.44(13) . . . 2 ? O3 Cu1 Cu2 O4 7.56(13) 2 . . 2 ? N1 Cu1 Cu2 O4 -104(100) . . . 2 ? O1 Cu1 Cu2 O2 6.97(13) 2 . . 2 ? O1 Cu1 Cu2 O2 -173.03(13) . . . 2 ? O3 Cu1 Cu2 O2 97.51(13) . . . 2 ? O3 Cu1 Cu2 O2 -82.49(13) 2 . . 2 ? N1 Cu1 Cu2 O2 166(100) . . . 2 ? O1 Cu1 Cu2 O2 -173.03(13) 2 . . . ? O1 Cu1 Cu2 O2 6.97(13) . . . . ? O3 Cu1 Cu2 O2 -82.49(13) . . . . ? O3 Cu1 Cu2 O2 97.51(13) 2 . . . ? N1 Cu1 Cu2 O2 -14(100) . . . . ? O1 Cu1 Cu2 N2 21(100) 2 . . . ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O3 Cu1 Cu2 N2 111(100) . . . . ? O3 Cu1 Cu2 N2 -69(100) 2 . . . ? N1 Cu1 Cu2 N2 0(42) . . . . ? C16 C15 N1 C15 -0.1(3) 1_565 . . 2 ? C16 C15 N1 Cu1 179.9(3) 1_565 . . . ? O1 Cu1 N1 C15 30.6(2) 2 . . 2 ? O1 Cu1 N1 C15 -149.4(2) . . . 2 ? O3 Cu1 N1 C15 -60.0(2) . . . 2 ? O3 Cu1 N1 C15 120.0(2) 2 . . 2 ? Cu2 Cu1 N1 C15 -129(100) . . . 2 ? O1 Cu1 N1 C15 -149.4(2) 2 . . . ? O1 Cu1 N1 C15 30.6(2) . . . . ? O3 Cu1 N1 C15 120.0(2) . . . . ? O3 Cu1 N1 C15 -60.0(2) 2 . . . ? Cu2 Cu1 N1 C15 51(100) . . . . ? C15 C16 N2 C16 -0.1(3) 1_545 . . 2 ? C15 C16 N2 Cu2 179.9(3) 1_545 . . . ? O4 Cu2 N2 C16 52.3(2) . . . 2 ? O4 Cu2 N2 C16 -127.7(2) 2 . . 2 ? O2 Cu2 N2 C16 -37.6(2) 2 . . 2 ? O2 Cu2 N2 C16 142.4(2) . . . 2 ? Cu1 Cu2 N2 C16 -51(100) . . . 2 ? O4 Cu2 N2 C16 -127.7(2) . . . . ? O4 Cu2 N2 C16 52.3(2) 2 . . . ? O2 Cu2 N2 C16 142.4(2) 2 . . . ? O2 Cu2 N2 C16 -37.6(2) . . . . ? Cu1 Cu2 N2 C16 129(100) . . . . ? O2 C1 O1 Cu1 6.7(6) . . . . ? C2 C1 O1 Cu1 -173.4(3) . . . . ? O1 Cu1 O1 C1 -9.2(3) 2 . . . ? O3 Cu1 O1 C1 74.3(3) . . . . ? O3 Cu1 O1 C1 -92.7(3) 2 . . . ? N1 Cu1 O1 C1 170.8(3) . . . . ? Cu2 Cu1 O1 C1 -9.2(3) . . . . ? O1 C1 O2 Cu2 2.9(6) . . . . ? C2 C1 O2 Cu2 -177.1(3) . . . . ? O4 Cu2 O2 C1 -92.9(3) . . . . ? O4 Cu2 O2 C1 78.1(3) 2 . . . ? O2 Cu2 O2 C1 -7.4(3) 2 . . . ? N2 Cu2 O2 C1 172.6(3) . . . . ? Cu1 Cu2 O2 C1 -7.4(3) . . . . ? O4 C8 O3 Cu1 1.5(6) . . . . ? C9 C8 O3 Cu1 -178.0(3) . . . . ? O1 Cu1 O3 C8 78.3(3) 2 . . . ? O1 Cu1 O3 C8 -93.0(3) . . . . ? O3 Cu1 O3 C8 -7.3(3) 2 . . . ? N1 Cu1 O3 C8 172.7(3) . . . . ? Cu2 Cu1 O3 C8 -7.3(3) . . . . ? O3 C8 O4 Cu2 8.9(6) . . . . ? C9 C8 O4 Cu2 -171.6(3) . . . . ? O4 Cu2 O4 C8 -10.9(3) 2 . . . ? O2 Cu2 O4 C8 -94.6(4) 2 . . . ? O2 Cu2 O4 C8 72.7(3) . . . . ? N2 Cu2 O4 C8 169.1(3) . . . . ? Cu1 Cu2 O4 C8 -10.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.420 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.075 #===END data_311131 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33.80 H31.18 Cu2 N2 O8' _chemical_formula_weight 720.44 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 C2/c 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 18.563(3) _cell_length_b 9.7095(13) _cell_length_c 19.354(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.259(3) _cell_angle_gamma 90.00 _cell_volume 3442.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.286 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5381 _exptl_absorpt_correction_T_max 0.8821 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12380 _diffrn_reflns_av_R_equivalents 0.0977 _diffrn_reflns_av_sigmaI/netI 0.1255 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4229 _reflns_number_gt 1858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0439P)^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 4229 _refine_ls_number_parameters 223 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1542 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.895 _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 C1 C 0.1237(2) 0.7310(4) 0.2116(2) 0.0442(11) Uani 1 1 d . . . C2 C 0.1982(2) 0.7309(4) 0.1917(2) 0.0476(12) Uani 1 1 d . . . C3 C 0.2278(3) 0.8512(5) 0.1701(3) 0.0710(17) Uani 1 1 d . . . H3 H 0.2011 0.9349 0.1694 0.085 Uiso 1 1 calc R . . C4 C 0.2950(3) 0.8509(6) 0.1500(4) 0.088(2) Uani 1 1 d . . . H4 H 0.3151 0.9341 0.1357 0.105 Uiso 1 1 calc R . . C5 C 0.3333(3) 0.7301(7) 0.1506(3) 0.0865(19) Uani 1 1 d . . . H5 H 0.3793 0.7289 0.1350 0.104 Uiso 1 1 calc R . . C6 C 0.3055(3) 0.6119(6) 0.1735(4) 0.081(2) Uani 1 1 d . . . H6 H 0.3330 0.5291 0.1759 0.097 Uiso 1 1 calc R . . C7 C 0.2382(3) 0.6123(5) 0.1931(3) 0.0631(16) Uani 1 1 d . . . H7 H 0.2187 0.5289 0.2080 0.076 Uiso 1 1 calc R . . C8 C 0.0647(2) 0.7225(5) 0.3757(3) 0.0488(12) Uani 1 1 d . . . C9 C 0.1043(3) 0.7190(5) 0.4486(3) 0.0537(12) Uani 1 1 d . . . C10 C 0.1391(3) 0.8334(6) 0.4778(4) 0.0833(19) Uani 1 1 d . . . H10 H 0.1376 0.9169 0.4520 0.100 Uiso 1 1 calc R . . C11 C 0.1770(4) 0.8266(7) 0.5457(4) 0.103(2) Uani 1 1 d . . . H11 H 0.2022 0.9060 0.5655 0.123 Uiso 1 1 calc R . . C12 C 0.1790(4) 0.7114(8) 0.5840(4) 0.105(2) Uani 1 1 d . . . H12 H 0.2046 0.7095 0.6307 0.126 Uiso 1 1 calc R . . C13 C 0.1439(4) 0.5975(7) 0.5552(4) 0.105(2) Uani 1 1 d . . . H13 H 0.1445 0.5155 0.5821 0.126 Uiso 1 1 calc R . . C14 C 0.1077(3) 0.6000(5) 0.4877(3) 0.0810(19) Uani 1 1 d . . . H14 H 0.0847 0.5187 0.4677 0.097 Uiso 1 1 calc R . . C15 C 0.0300(2) 1.1560(4) 0.2044(3) 0.0455(12) Uani 1 1 d . . . H15 H 0.0524 1.1081 0.1706 0.055 Uiso 1 1 calc R . . C16 C 0.0301(2) 0.2981(4) 0.2037(2) 0.0438(11) Uani 1 1 d . . . H16 H 0.0520 0.3456 0.1695 0.053 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85956(6) 0.2500 0.0424(3) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59307(6) 0.2500 0.0441(3) Uani 1 2 d S . . N1 N 0.0000 1.0842(4) 0.2500 0.0375(13) Uani 1 2 d S . . N2 N 0.0000 0.3691(4) 0.2500 0.0384(13) Uani 1 2 d S . . O1 O 0.09217(16) 0.8444(3) 0.21407(18) 0.0536(9) Uani 1 1 d . . . O2 O 0.09795(16) 0.6156(3) 0.22529(18) 0.0542(9) Uani 1 1 d . . . O3 O 0.05510(16) 0.8373(3) 0.34556(16) 0.0533(9) Uani 1 1 d . . . O4 O 0.04223(18) 0.6085(3) 0.34889(17) 0.0573(10) Uani 1 1 d . . . C1S C 0.0733(5) 0.8059(9) 0.0129(5) 0.175(6) Uani 0.898(17) 1 d PD . . H1S H 0.052(4) 0.847(8) -0.031(2) 0.263 Uiso 0.898(17) 1 d PD . . H2S H 0.1251(9) 0.799(9) 0.014(5) 0.263 Uiso 0.898(17) 1 d PD . . H3S H 0.063(5) 0.862(8) 0.051(3) 0.263 Uiso 0.898(17) 1 d PD . . H4S H 0.053(4) 0.715(4) 0.017(5) 0.263 Uiso 0.898(17) 1 d PD . . 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 C1 0.053(3) 0.033(2) 0.046(3) -0.003(2) 0.005(2) -0.001(2) C2 0.046(3) 0.042(2) 0.055(3) -0.007(2) 0.008(2) 0.002(2) C3 0.060(4) 0.064(3) 0.094(5) 0.017(3) 0.028(3) 0.003(3) C4 0.060(4) 0.102(5) 0.107(6) 0.026(4) 0.031(4) -0.009(4) C5 0.046(4) 0.127(5) 0.087(5) -0.007(4) 0.012(3) 0.011(4) C6 0.056(4) 0.087(4) 0.098(6) -0.017(4) 0.004(4) 0.022(3) C7 0.052(4) 0.054(3) 0.082(5) -0.011(3) 0.006(3) 0.009(2) C8 0.051(3) 0.042(2) 0.055(3) -0.002(3) 0.014(2) -0.001(2) C9 0.060(3) 0.055(3) 0.046(3) -0.002(3) 0.009(2) 0.000(3) C10 0.108(5) 0.072(3) 0.066(5) -0.007(3) 0.001(4) -0.014(3) C11 0.121(6) 0.099(5) 0.079(6) -0.025(4) -0.010(5) -0.021(4) C12 0.113(6) 0.128(6) 0.064(5) -0.003(5) -0.013(4) 0.013(5) C13 0.142(7) 0.104(5) 0.060(5) 0.012(4) -0.006(5) 0.011(5) C14 0.104(5) 0.071(4) 0.064(5) 0.005(3) 0.002(4) 0.002(3) C15 0.058(3) 0.025(2) 0.058(4) -0.002(2) 0.024(2) 0.0023(19) C16 0.060(3) 0.029(3) 0.048(3) 0.008(2) 0.025(2) 0.0033(19) Cu1 0.0545(6) 0.0157(3) 0.0593(7) 0.000 0.0162(4) 0.000 Cu2 0.0596(6) 0.0167(3) 0.0568(7) 0.000 0.0116(5) 0.000 N1 0.046(3) 0.020(2) 0.047(4) 0.000 0.010(3) 0.000 N2 0.046(3) 0.024(2) 0.048(4) 0.000 0.018(3) 0.000 O1 0.057(2) 0.0286(16) 0.080(3) 0.0040(15) 0.0249(18) 0.0067(14) O2 0.057(2) 0.0298(15) 0.080(3) 0.0000(15) 0.0213(18) -0.0004(14) O3 0.072(2) 0.0323(16) 0.055(3) 0.0009(14) 0.0076(18) -0.0053(14) O4 0.082(3) 0.0349(16) 0.052(3) 0.0009(14) 0.0029(19) -0.0010(15) C1S 0.195(11) 0.201(11) 0.141(11) -0.014(8) 0.061(8) -0.065(8) _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 C1 O1 1.251(5) . ? C1 O2 1.263(4) . ? C1 C2 1.494(6) . ? C2 C7 1.368(5) . ? C2 C3 1.383(6) . ? C3 C4 1.365(7) . ? C4 C5 1.370(7) . ? C5 C6 1.362(7) . ? C6 C7 1.363(7) . ? C8 O3 1.257(5) . ? C8 O4 1.265(5) . ? C8 C9 1.482(6) . ? C9 C10 1.362(6) . ? C9 C14 1.377(6) . ? C10 C11 1.388(8) . ? C11 C12 1.340(8) . ? C12 C13 1.357(8) . ? C13 C14 1.370(8) . ? C15 N1 1.317(4) . ? C15 C16 1.380(5) 1_565 ? C16 N2 1.323(4) . ? C16 C15 1.380(5) 1_545 ? Cu1 O1 1.953(3) . ? Cu1 O1 1.953(3) 2 ? Cu1 O3 1.976(3) 2 ? Cu1 O3 1.976(3) . ? Cu1 N1 2.181(4) . ? Cu1 Cu2 2.5875(8) . ? Cu2 O4 1.954(3) 2 ? Cu2 O4 1.954(3) . ? Cu2 O2 1.965(3) . ? Cu2 O2 1.965(3) 2 ? Cu2 N2 2.175(4) . ? N1 C15 1.317(4) 2 ? N2 C16 1.323(4) 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 O1 C1 O2 125.3(4) . . ? O1 C1 C2 117.9(4) . . ? O2 C1 C2 116.8(4) . . ? C7 C2 C3 118.5(5) . . ? C7 C2 C1 121.1(4) . . ? C3 C2 C1 120.4(4) . . ? C4 C3 C2 120.6(5) . . ? C3 C4 C5 119.8(5) . . ? C6 C5 C4 120.0(6) . . ? C5 C6 C7 120.1(5) . . ? C6 C7 C2 121.0(5) . . ? O3 C8 O4 124.9(4) . . ? O3 C8 C9 118.3(4) . . ? O4 C8 C9 116.8(4) . . ? C10 C9 C14 118.6(5) . . ? C10 C9 C8 120.4(5) . . ? C14 C9 C8 121.0(5) . . ? C9 C10 C11 119.3(6) . . ? C12 C11 C10 121.9(6) . . ? C11 C12 C13 118.9(6) . . ? C12 C13 C14 120.5(6) . . ? C13 C14 C9 120.8(6) . . ? N1 C15 C16 122.5(4) . 1_565 ? N2 C16 C15 120.9(4) . 1_545 ? O1 Cu1 O1 171.34(15) . 2 ? O1 Cu1 O3 90.55(14) . 2 ? O1 Cu1 O3 88.50(14) 2 2 ? O1 Cu1 O3 88.50(14) . . ? O1 Cu1 O3 90.55(14) 2 . ? O3 Cu1 O3 167.45(16) 2 . ? O1 Cu1 N1 94.33(7) . . ? O1 Cu1 N1 94.33(7) 2 . ? O3 Cu1 N1 96.28(8) 2 . ? O3 Cu1 N1 96.28(8) . . ? O1 Cu1 Cu2 85.67(7) . . ? O1 Cu1 Cu2 85.67(7) 2 . ? O3 Cu1 Cu2 83.72(8) 2 . ? O3 Cu1 Cu2 83.72(8) . . ? N1 Cu1 Cu2 180.000(1) . . ? O4 Cu2 O4 171.20(16) 2 . ? O4 Cu2 O2 89.67(14) 2 . ? O4 Cu2 O2 89.36(14) . . ? O4 Cu2 O2 89.36(14) 2 2 ? O4 Cu2 O2 89.67(14) . 2 ? O2 Cu2 O2 167.23(15) . 2 ? O4 Cu2 N2 94.40(8) 2 . ? O4 Cu2 N2 94.40(8) . . ? O2 Cu2 N2 96.39(8) . . ? O2 Cu2 N2 96.39(8) 2 . ? O4 Cu2 Cu1 85.60(8) 2 . ? O4 Cu2 Cu1 85.60(8) . . ? O2 Cu2 Cu1 83.61(8) . . ? O2 Cu2 Cu1 83.61(8) 2 . ? N2 Cu2 Cu1 180.0 . . ? C15 N1 C15 116.0(5) . 2 ? C15 N1 Cu1 122.0(2) . . ? C15 N1 Cu1 122.0(2) 2 . ? C16 N2 C16 117.2(5) . 2 ? C16 N2 Cu2 121.4(2) . . ? C16 N2 Cu2 121.4(2) 2 . ? C1 O1 Cu1 121.5(3) . . ? C1 O2 Cu2 123.1(3) . . ? C8 O3 Cu1 123.0(3) . . ? C8 O4 Cu2 121.5(3) . . ? 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 C7 174.8(4) . . . . ? O2 C1 C2 C7 -4.4(7) . . . . ? O1 C1 C2 C3 -6.2(7) . . . . ? O2 C1 C2 C3 174.5(4) . . . . ? C7 C2 C3 C4 0.8(9) . . . . ? C1 C2 C3 C4 -178.1(5) . . . . ? C2 C3 C4 C5 0.5(10) . . . . ? C3 C4 C5 C6 -2.3(10) . . . . ? C4 C5 C6 C7 2.8(10) . . . . ? C5 C6 C7 C2 -1.4(9) . . . . ? C3 C2 C7 C6 -0.4(8) . . . . ? C1 C2 C7 C6 178.6(5) . . . . ? O3 C8 C9 C10 -10.4(7) . . . . ? O4 C8 C9 C10 170.7(5) . . . . ? O3 C8 C9 C14 170.8(5) . . . . ? O4 C8 C9 C14 -8.1(7) . . . . ? C14 C9 C10 C11 0.1(9) . . . . ? C8 C9 C10 C11 -178.7(6) . . . . ? C9 C10 C11 C12 -1.5(12) . . . . ? C10 C11 C12 C13 1.1(12) . . . . ? C11 C12 C13 C14 0.7(12) . . . . ? C12 C13 C14 C9 -2.1(11) . . . . ? C10 C9 C14 C13 1.6(10) . . . . ? C8 C9 C14 C13 -179.6(6) . . . . ? O1 Cu1 Cu2 O4 -83.51(14) . . . 2 ? O1 Cu1 Cu2 O4 96.49(14) 2 . . 2 ? O3 Cu1 Cu2 O4 7.52(14) 2 . . 2 ? O3 Cu1 Cu2 O4 -172.48(14) . . . 2 ? N1 Cu1 Cu2 O4 -104(42) . . . 2 ? O1 Cu1 Cu2 O4 96.49(14) . . . . ? O1 Cu1 Cu2 O4 -83.51(14) 2 . . . ? O3 Cu1 Cu2 O4 -172.48(14) 2 . . . ? O3 Cu1 Cu2 O4 7.52(14) . . . . ? N1 Cu1 Cu2 O4 76(44) . . . . ? O1 Cu1 Cu2 O2 6.65(14) . . . . ? O1 Cu1 Cu2 O2 -173.35(14) 2 . . . ? O3 Cu1 Cu2 O2 97.68(14) 2 . . . ? O3 Cu1 Cu2 O2 -82.32(14) . . . . ? N1 Cu1 Cu2 O2 -14(42) . . . . ? O1 Cu1 Cu2 O2 -173.35(14) . . . 2 ? O1 Cu1 Cu2 O2 6.65(14) 2 . . 2 ? O3 Cu1 Cu2 O2 -82.32(14) 2 . . 2 ? O3 Cu1 Cu2 O2 97.68(14) . . . 2 ? N1 Cu1 Cu2 O2 166(44) . . . 2 ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O1 Cu1 Cu2 N2 21(100) 2 . . . ? O3 Cu1 Cu2 N2 -68(100) 2 . . . ? O3 Cu1 Cu2 N2 112(100) . . . . ? N1 Cu1 Cu2 N2 0(43) . . . . ? C16 C15 N1 C15 -0.2(3) 1_565 . . 2 ? C16 C15 N1 Cu1 179.8(3) 1_565 . . . ? O1 Cu1 N1 C15 30.7(2) . . . . ? O1 Cu1 N1 C15 -149.3(2) 2 . . . ? O3 Cu1 N1 C15 -60.4(2) 2 . . . ? O3 Cu1 N1 C15 119.6(2) . . . . ? Cu2 Cu1 N1 C15 51(41) . . . . ? O1 Cu1 N1 C15 -149.3(2) . . . 2 ? O1 Cu1 N1 C15 30.7(2) 2 . . 2 ? O3 Cu1 N1 C15 119.6(2) 2 . . 2 ? O3 Cu1 N1 C15 -60.4(2) . . . 2 ? Cu2 Cu1 N1 C15 -129(44) . . . 2 ? C15 C16 N2 C16 -0.2(3) 1_545 . . 2 ? C15 C16 N2 Cu2 179.8(3) 1_545 . . . ? O4 Cu2 N2 C16 52.6(2) 2 . . . ? O4 Cu2 N2 C16 -127.4(2) . . . . ? O2 Cu2 N2 C16 -37.6(2) . . . . ? O2 Cu2 N2 C16 142.4(2) 2 . . . ? Cu1 Cu2 N2 C16 128(100) . . . . ? O4 Cu2 N2 C16 -127.4(2) 2 . . 2 ? O4 Cu2 N2 C16 52.6(2) . . . 2 ? O2 Cu2 N2 C16 142.4(2) . . . 2 ? O2 Cu2 N2 C16 -37.6(2) 2 . . 2 ? Cu1 Cu2 N2 C16 -52(100) . . . 2 ? O2 C1 O1 Cu1 6.5(6) . . . . ? C2 C1 O1 Cu1 -172.7(3) . . . . ? O1 Cu1 O1 C1 -8.8(3) 2 . . . ? O3 Cu1 O1 C1 -92.5(3) 2 . . . ? O3 Cu1 O1 C1 75.0(3) . . . . ? N1 Cu1 O1 C1 171.2(3) . . . . ? Cu2 Cu1 O1 C1 -8.8(3) . . . . ? O1 C1 O2 Cu2 2.5(6) . . . . ? C2 C1 O2 Cu2 -178.3(3) . . . . ? O4 Cu2 O2 C1 78.6(3) 2 . . . ? O4 Cu2 O2 C1 -92.6(3) . . . . ? O2 Cu2 O2 C1 -7.0(3) 2 . . . ? N2 Cu2 O2 C1 173.0(3) . . . . ? Cu1 Cu2 O2 C1 -7.0(3) . . . . ? O4 C8 O3 Cu1 1.4(7) . . . . ? C9 C8 O3 Cu1 -177.4(3) . . . . ? O1 Cu1 O3 C8 -93.1(4) . . . . ? O1 Cu1 O3 C8 78.3(4) 2 . . . ? O3 Cu1 O3 C8 -7.3(3) 2 . . . ? N1 Cu1 O3 C8 172.7(3) . . . . ? Cu2 Cu1 O3 C8 -7.3(3) . . . . ? O3 C8 O4 Cu2 8.8(6) . . . . ? C9 C8 O4 Cu2 -172.4(3) . . . . ? O4 Cu2 O4 C8 -10.7(3) 2 . . . ? O2 Cu2 O4 C8 73.0(4) . . . . ? O2 Cu2 O4 C8 -94.3(4) 2 . . . ? N2 Cu2 O4 C8 169.3(3) . . . . ? Cu1 Cu2 O4 C8 -10.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.749 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.085 #===END data_311151 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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 C2/c 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 18.604(2) _cell_length_b 9.7172(12) _cell_length_c 19.352(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.399(3) _cell_angle_gamma 90.00 _cell_volume 3451.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.283 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6213 _exptl_absorpt_correction_T_max 0.9043 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12479 _diffrn_reflns_av_R_equivalents 0.1250 _diffrn_reflns_av_sigmaI/netI 0.1563 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4256 _reflns_number_gt 1635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0343P)^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 4256 _refine_ls_number_parameters 222 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1779 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.845 _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 C1 C 0.1235(2) 0.7307(5) 0.2113(2) 0.0434(12) Uani 1 1 d . . . C2 C 0.1976(2) 0.7323(5) 0.1912(2) 0.0442(12) Uani 1 1 d . . . C3 C 0.2268(3) 0.8519(5) 0.1705(3) 0.0656(17) Uani 1 1 d . . . H3 H 0.2006 0.9336 0.1704 0.079 Uiso 1 1 calc R . . C4 C 0.2941(4) 0.8529(6) 0.1501(4) 0.090(2) Uani 1 1 d . . . H4 H 0.3133 0.9344 0.1357 0.108 Uiso 1 1 calc R . . C5 C 0.3330(3) 0.7316(8) 0.1512(3) 0.0875(19) Uani 1 1 d . . . H5 H 0.3781 0.7311 0.1366 0.105 Uiso 1 1 calc R . . C6 C 0.3055(3) 0.6124(6) 0.1738(4) 0.077(2) Uani 1 1 d . . . H6 H 0.3323 0.5313 0.1757 0.092 Uiso 1 1 calc R . . C7 C 0.2383(3) 0.6130(5) 0.1936(3) 0.0616(18) Uani 1 1 d . . . H7 H 0.2196 0.5318 0.2090 0.074 Uiso 1 1 calc R . . C8 C 0.0648(2) 0.7214(5) 0.3761(3) 0.0470(12) Uani 1 1 d . . . C9 C 0.1053(3) 0.7186(5) 0.4488(3) 0.0537(13) Uani 1 1 d . . . C10 C 0.1400(3) 0.8341(6) 0.4782(4) 0.0771(19) Uani 1 1 d . . . H10 H 0.1381 0.9158 0.4529 0.092 Uiso 1 1 calc R . . C11 C 0.1778(4) 0.8276(7) 0.5461(4) 0.095(2) Uani 1 1 d . . . H11 H 0.2026 0.9049 0.5657 0.114 Uiso 1 1 calc R . . C12 C 0.1792(4) 0.7101(8) 0.5844(4) 0.101(2) Uani 1 1 d . . . H12 H 0.2044 0.7075 0.6301 0.121 Uiso 1 1 calc R . . C13 C 0.1437(4) 0.5967(7) 0.5556(4) 0.106(3) Uani 1 1 d . . . H13 H 0.1439 0.5164 0.5818 0.127 Uiso 1 1 calc R . . C14 C 0.1079(3) 0.6003(5) 0.4887(4) 0.080(2) Uani 1 1 d . . . H14 H 0.0846 0.5214 0.4692 0.096 Uiso 1 1 calc R . . C15 C 0.0304(2) 1.1556(4) 0.2037(3) 0.0449(13) Uani 1 1 d . . . H15 H 0.0523 1.1085 0.1708 0.054 Uiso 1 1 calc R . . C16 C 0.0302(2) 0.2985(4) 0.2032(2) 0.0421(13) Uani 1 1 d . . . H16 H 0.0513 0.3457 0.1698 0.051 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85938(6) 0.2500 0.0429(3) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59282(6) 0.2500 0.0450(3) Uani 1 2 d S . . N1 N 0.0000 1.0847(5) 0.2500 0.0366(16) Uani 1 2 d S . . N2 N 0.0000 0.3681(5) 0.2500 0.0379(16) Uani 1 2 d S . . O1 O 0.09121(16) 0.8443(3) 0.21349(18) 0.0510(10) Uani 1 1 d . . . O2 O 0.09744(17) 0.6156(3) 0.22506(19) 0.0536(10) Uani 1 1 d . . . O3 O 0.05507(17) 0.8364(3) 0.34515(17) 0.0526(10) Uani 1 1 d . . . O4 O 0.04242(18) 0.6082(3) 0.34862(17) 0.0571(11) Uani 1 1 d . . . C1S C 0.0733(4) 0.8072(8) 0.0128(4) 0.175(4) Uani 1 1 d D . . H1S H 0.1247(8) 0.799(8) 0.013(4) 0.263 Uiso 1 1 d D . . H2S H 0.065(4) 0.870(6) 0.049(3) 0.263 Uiso 1 1 d D . . H3S H 0.050(4) 0.840(7) -0.0321(18) 0.263 Uiso 1 1 d D . . H4S H 0.054(4) 0.719(3) 0.022(4) 0.263 Uiso 1 1 d 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 C1 0.051(3) 0.034(2) 0.045(3) 0.002(3) 0.009(3) 0.003(3) C2 0.040(3) 0.046(3) 0.048(3) -0.005(3) 0.010(3) 0.003(2) C3 0.050(4) 0.056(3) 0.095(5) 0.016(3) 0.022(4) -0.001(3) C4 0.058(5) 0.098(5) 0.118(7) 0.026(4) 0.022(4) -0.006(4) C5 0.048(4) 0.130(6) 0.085(5) -0.006(5) 0.013(4) 0.004(4) C6 0.049(4) 0.086(4) 0.094(6) -0.021(4) 0.005(4) 0.020(3) C7 0.053(4) 0.043(3) 0.086(5) -0.011(3) 0.003(4) 0.010(2) C8 0.050(3) 0.039(2) 0.053(4) -0.002(3) 0.014(3) 0.000(3) C9 0.059(3) 0.055(3) 0.044(3) -0.004(3) 0.002(3) 0.002(3) C10 0.097(5) 0.071(4) 0.061(5) -0.007(3) 0.004(4) -0.016(4) C11 0.103(6) 0.091(5) 0.082(6) -0.024(4) -0.013(5) -0.008(4) C12 0.110(6) 0.120(6) 0.063(5) -0.002(5) -0.013(4) 0.010(5) C13 0.146(7) 0.100(5) 0.060(5) 0.018(4) -0.019(5) 0.001(5) C14 0.110(6) 0.063(4) 0.063(5) 0.011(3) 0.000(4) 0.001(4) C15 0.057(3) 0.029(3) 0.054(4) -0.004(2) 0.023(3) 0.002(2) C16 0.060(3) 0.020(3) 0.053(4) 0.002(2) 0.028(3) -0.002(2) Cu1 0.0549(6) 0.0156(4) 0.0596(7) 0.000 0.0138(6) 0.000 Cu2 0.0592(7) 0.0152(4) 0.0606(8) 0.000 0.0096(6) 0.000 N1 0.042(4) 0.024(3) 0.047(4) 0.000 0.015(3) 0.000 N2 0.047(4) 0.021(3) 0.046(4) 0.000 0.009(4) 0.000 O1 0.059(2) 0.0281(17) 0.070(3) 0.0015(16) 0.024(2) 0.0075(15) O2 0.059(3) 0.0245(17) 0.082(3) 0.0013(16) 0.025(2) 0.0011(14) O3 0.071(2) 0.0322(17) 0.053(3) 0.0001(16) 0.006(2) -0.0025(16) O4 0.084(3) 0.0306(18) 0.053(3) -0.0015(15) -0.001(2) -0.0018(16) C1S 0.169(8) 0.194(9) 0.169(9) -0.018(7) 0.045(7) -0.048(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 C1 O1 1.260(5) . ? C1 O2 1.264(4) . ? C1 C2 1.494(6) . ? C2 C3 1.370(6) . ? C2 C7 1.380(5) . ? C3 C4 1.374(7) . ? C4 C5 1.381(7) . ? C5 C6 1.367(7) . ? C6 C7 1.366(6) . ? C8 O4 1.263(5) . ? C8 O3 1.267(5) . ? C8 C9 1.484(6) . ? C9 C10 1.371(6) . ? C9 C14 1.381(6) . ? C10 C11 1.387(8) . ? C11 C12 1.359(8) . ? C12 C13 1.357(7) . ? C13 C14 1.357(8) . ? C15 N1 1.328(4) . ? C15 C16 1.388(5) 1_565 ? C16 N2 1.326(4) . ? C16 C15 1.388(5) 1_545 ? Cu1 O1 1.947(3) 2 ? Cu1 O1 1.947(3) . ? Cu1 O3 1.968(3) 2 ? Cu1 O3 1.968(3) . ? Cu1 N1 2.190(5) . ? Cu1 Cu2 2.5902(9) . ? Cu2 O4 1.948(3) . ? Cu2 O4 1.948(3) 2 ? Cu2 O2 1.963(3) . ? Cu2 O2 1.963(3) 2 ? Cu2 N2 2.184(5) . ? N1 C15 1.328(4) 2 ? N2 C16 1.326(4) 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 O1 C1 O2 124.5(4) . . ? O1 C1 C2 117.7(4) . . ? O2 C1 C2 117.8(4) . . ? C3 C2 C7 118.9(4) . . ? C3 C2 C1 120.7(4) . . ? C7 C2 C1 120.4(5) . . ? C2 C3 C4 120.8(5) . . ? C3 C4 C5 119.3(6) . . ? C6 C5 C4 120.4(6) . . ? C7 C6 C5 119.6(5) . . ? C6 C7 C2 121.0(5) . . ? O4 C8 O3 123.8(4) . . ? O4 C8 C9 117.7(4) . . ? O3 C8 C9 118.5(4) . . ? C10 C9 C14 118.6(5) . . ? C10 C9 C8 120.7(5) . . ? C14 C9 C8 120.7(5) . . ? C9 C10 C11 119.1(6) . . ? C12 C11 C10 121.2(6) . . ? C13 C12 C11 119.5(6) . . ? C14 C13 C12 120.1(7) . . ? C13 C14 C9 121.4(6) . . ? N1 C15 C16 121.5(5) . 1_565 ? N2 C16 C15 120.4(5) . 1_545 ? O1 Cu1 O1 171.35(16) 2 . ? O1 Cu1 O3 88.83(14) 2 2 ? O1 Cu1 O3 90.19(14) . 2 ? O1 Cu1 O3 90.19(14) 2 . ? O1 Cu1 O3 88.83(14) . . ? O3 Cu1 O3 166.94(17) 2 . ? O1 Cu1 N1 94.33(8) 2 . ? O1 Cu1 N1 94.33(8) . . ? O3 Cu1 N1 96.53(9) 2 . ? O3 Cu1 N1 96.53(9) . . ? O1 Cu1 Cu2 85.67(8) 2 . ? O1 Cu1 Cu2 85.67(8) . . ? O3 Cu1 Cu2 83.47(9) 2 . ? O3 Cu1 Cu2 83.47(9) . . ? N1 Cu1 Cu2 180.000(1) . . ? O4 Cu2 O4 171.19(17) . 2 ? O4 Cu2 O2 89.40(15) . . ? O4 Cu2 O2 89.60(15) 2 . ? O4 Cu2 O2 89.60(15) . 2 ? O4 Cu2 O2 89.40(15) 2 2 ? O2 Cu2 O2 167.02(16) . 2 ? O4 Cu2 N2 94.40(8) . . ? O4 Cu2 N2 94.40(8) 2 . ? O2 Cu2 N2 96.49(8) . . ? O2 Cu2 N2 96.49(8) 2 . ? O4 Cu2 Cu1 85.60(8) . . ? O4 Cu2 Cu1 85.60(8) 2 . ? O2 Cu2 Cu1 83.51(8) . . ? O2 Cu2 Cu1 83.51(8) 2 . ? N2 Cu2 Cu1 180.0 . . ? C15 N1 C15 117.5(5) 2 . ? C15 N1 Cu1 121.3(3) 2 . ? C15 N1 Cu1 121.3(3) . . ? C16 N2 C16 118.7(5) . 2 ? C16 N2 Cu2 120.6(3) . . ? C16 N2 Cu2 120.6(3) 2 . ? C1 O1 Cu1 121.8(3) . . ? C1 O2 Cu2 123.6(3) . . ? C8 O3 Cu1 123.8(3) . . ? C8 O4 Cu2 122.2(3) . . ? 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 C3 -5.0(7) . . . . ? O2 C1 C2 C3 175.0(5) . . . . ? O1 C1 C2 C7 174.4(4) . . . . ? O2 C1 C2 C7 -5.5(7) . . . . ? C7 C2 C3 C4 2.4(9) . . . . ? C1 C2 C3 C4 -178.1(6) . . . . ? C2 C3 C4 C5 -0.7(10) . . . . ? C3 C4 C5 C6 -1.3(10) . . . . ? C4 C5 C6 C7 1.7(10) . . . . ? C5 C6 C7 C2 0.1(10) . . . . ? C3 C2 C7 C6 -2.1(8) . . . . ? C1 C2 C7 C6 178.5(5) . . . . ? O4 C8 C9 C10 170.6(5) . . . . ? O3 C8 C9 C10 -8.9(7) . . . . ? O4 C8 C9 C14 -10.4(7) . . . . ? O3 C8 C9 C14 170.0(5) . . . . ? C14 C9 C10 C11 1.5(9) . . . . ? C8 C9 C10 C11 -179.5(5) . . . . ? C9 C10 C11 C12 -1.9(11) . . . . ? C10 C11 C12 C13 0.7(11) . . . . ? C11 C12 C13 C14 0.9(12) . . . . ? C12 C13 C14 C9 -1.3(11) . . . . ? C10 C9 C14 C13 0.1(10) . . . . ? C8 C9 C14 C13 -178.9(6) . . . . ? O1 Cu1 Cu2 O4 -83.19(14) 2 . . . ? O1 Cu1 Cu2 O4 96.81(14) . . . . ? O3 Cu1 Cu2 O4 -172.51(15) 2 . . . ? O3 Cu1 Cu2 O4 7.49(15) . . . . ? N1 Cu1 Cu2 O4 76(48) . . . . ? O1 Cu1 Cu2 O4 96.81(14) 2 . . 2 ? O1 Cu1 Cu2 O4 -83.19(14) . . . 2 ? O3 Cu1 Cu2 O4 7.49(15) 2 . . 2 ? O3 Cu1 Cu2 O4 -172.51(15) . . . 2 ? N1 Cu1 Cu2 O4 -104(46) . . . 2 ? O1 Cu1 Cu2 O2 -173.09(16) 2 . . . ? O1 Cu1 Cu2 O2 6.91(16) . . . . ? O3 Cu1 Cu2 O2 97.59(14) 2 . . . ? O3 Cu1 Cu2 O2 -82.41(14) . . . . ? N1 Cu1 Cu2 O2 -14(46) . . . . ? O1 Cu1 Cu2 O2 6.91(16) 2 . . 2 ? O1 Cu1 Cu2 O2 -173.09(16) . . . 2 ? O3 Cu1 Cu2 O2 -82.41(14) 2 . . 2 ? O3 Cu1 Cu2 O2 97.59(14) . . . 2 ? N1 Cu1 Cu2 O2 166(48) . . . 2 ? O1 Cu1 Cu2 N2 21(100) 2 . . . ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O3 Cu1 Cu2 N2 -68(100) 2 . . . ? O3 Cu1 Cu2 N2 112(100) . . . . ? N1 Cu1 Cu2 N2 0(47) . . . . ? C16 C15 N1 C15 -0.4(3) 1_565 . . 2 ? C16 C15 N1 Cu1 179.6(3) 1_565 . . . ? O1 Cu1 N1 C15 30.1(2) 2 . . 2 ? O1 Cu1 N1 C15 -149.9(2) . . . 2 ? O3 Cu1 N1 C15 119.5(2) 2 . . 2 ? O3 Cu1 N1 C15 -60.5(2) . . . 2 ? Cu2 Cu1 N1 C15 -129(48) . . . 2 ? O1 Cu1 N1 C15 -149.9(2) 2 . . . ? O1 Cu1 N1 C15 30.1(2) . . . . ? O3 Cu1 N1 C15 -60.5(2) 2 . . . ? O3 Cu1 N1 C15 119.5(2) . . . . ? Cu2 Cu1 N1 C15 51(46) . . . . ? C15 C16 N2 C16 -0.4(3) 1_545 . . 2 ? C15 C16 N2 Cu2 179.6(3) 1_545 . . . ? O4 Cu2 N2 C16 -127.4(2) . . . . ? O4 Cu2 N2 C16 52.6(2) 2 . . . ? O2 Cu2 N2 C16 -37.5(2) . . . . ? O2 Cu2 N2 C16 142.5(2) 2 . . . ? Cu1 Cu2 N2 C16 128(100) . . . . ? O4 Cu2 N2 C16 52.6(2) . . . 2 ? O4 Cu2 N2 C16 -127.4(2) 2 . . 2 ? O2 Cu2 N2 C16 142.5(2) . . . 2 ? O2 Cu2 N2 C16 -37.5(2) 2 . . 2 ? Cu1 Cu2 N2 C16 -52(100) . . . 2 ? O2 C1 O1 Cu1 7.7(6) . . . . ? C2 C1 O1 Cu1 -172.2(3) . . . . ? O1 Cu1 O1 C1 -9.6(4) 2 . . . ? O3 Cu1 O1 C1 -93.1(4) 2 . . . ? O3 Cu1 O1 C1 73.9(4) . . . . ? N1 Cu1 O1 C1 170.4(4) . . . . ? Cu2 Cu1 O1 C1 -9.6(4) . . . . ? O1 C1 O2 Cu2 1.8(6) . . . . ? C2 C1 O2 Cu2 -178.3(3) . . . . ? O4 Cu2 O2 C1 -92.5(4) . . . . ? O4 Cu2 O2 C1 78.8(4) 2 . . . ? O2 Cu2 O2 C1 -6.9(3) 2 . . . ? N2 Cu2 O2 C1 173.1(3) . . . . ? Cu1 Cu2 O2 C1 -6.9(3) . . . . ? O4 C8 O3 Cu1 2.5(6) . . . . ? C9 C8 O3 Cu1 -178.0(3) . . . . ? O1 Cu1 O3 C8 77.9(4) 2 . . . ? O1 Cu1 O3 C8 -93.5(4) . . . . ? O3 Cu1 O3 C8 -7.7(3) 2 . . . ? N1 Cu1 O3 C8 172.3(3) . . . . ? Cu2 Cu1 O3 C8 -7.7(3) . . . . ? O3 C8 O4 Cu2 7.8(6) . . . . ? C9 C8 O4 Cu2 -171.7(3) . . . . ? O4 Cu2 O4 C8 -10.3(3) 2 . . . ? O2 Cu2 O4 C8 73.3(4) . . . . ? O2 Cu2 O4 C8 -93.8(4) 2 . . . ? N2 Cu2 O4 C8 169.7(3) . . . . ? Cu1 Cu2 O4 C8 -10.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.456 _refine_diff_density_min -0.775 _refine_diff_density_rms 0.073 #===END data_311241 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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 C2/c 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 18.600(3) _cell_length_b 9.7110(16) _cell_length_c 19.362(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.346(4) _cell_angle_gamma 90.00 _cell_volume 3450.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.283 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5132 _exptl_absorpt_correction_T_max 0.8612 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9614 _diffrn_reflns_av_R_equivalents 0.2463 _diffrn_reflns_av_sigmaI/netI 0.2457 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3055 _reflns_number_gt 1354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0375P)^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 3055 _refine_ls_number_parameters 222 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1862 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.872 _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 C1 C 0.1238(3) 0.7303(6) 0.2117(3) 0.0392(15) Uani 1 1 d . . . C2 C 0.1974(3) 0.7315(6) 0.1912(3) 0.0430(16) Uani 1 1 d . . . C3 C 0.2270(4) 0.8516(7) 0.1701(4) 0.065(2) Uani 1 1 d . . . H3 H 0.2010 0.9336 0.1695 0.078 Uiso 1 1 calc R . . C4 C 0.2940(5) 0.8514(9) 0.1501(5) 0.086(3) Uani 1 1 d . . . H4 H 0.3136 0.9329 0.1361 0.103 Uiso 1 1 calc R . . C5 C 0.3323(4) 0.7317(11) 0.1504(4) 0.082(2) Uani 1 1 d . . . H5 H 0.3769 0.7313 0.1347 0.099 Uiso 1 1 calc R . . C6 C 0.3058(5) 0.6133(9) 0.1736(5) 0.076(3) Uani 1 1 d . . . H6 H 0.3332 0.5329 0.1757 0.091 Uiso 1 1 calc R . . C7 C 0.2377(5) 0.6123(7) 0.1941(4) 0.059(2) Uani 1 1 d . . . H7 H 0.2194 0.5311 0.2099 0.071 Uiso 1 1 calc R . . C8 C 0.0649(3) 0.7225(7) 0.3769(4) 0.0499(18) Uani 1 1 d . . . C9 C 0.1051(4) 0.7180(7) 0.4482(3) 0.0490(17) Uani 1 1 d . . . C10 C 0.1407(5) 0.8336(7) 0.4785(5) 0.070(3) Uani 1 1 d . . . H10 H 0.1398 0.9151 0.4532 0.084 Uiso 1 1 calc R . . C11 C 0.1773(6) 0.8279(9) 0.5456(6) 0.095(3) Uani 1 1 d . . . H11 H 0.2014 0.9059 0.5653 0.114 Uiso 1 1 calc R . . C12 C 0.1793(5) 0.7111(12) 0.5842(4) 0.100(3) Uani 1 1 d . . . H12 H 0.2047 0.7084 0.6296 0.121 Uiso 1 1 calc R . . C13 C 0.1432(6) 0.5974(10) 0.5550(6) 0.110(4) Uani 1 1 d . . . H13 H 0.1431 0.5174 0.5814 0.132 Uiso 1 1 calc R . . C14 C 0.1079(5) 0.5999(7) 0.4887(5) 0.078(3) Uani 1 1 d . . . H14 H 0.0849 0.5205 0.4695 0.093 Uiso 1 1 calc R . . C15 C 0.0303(3) 1.1557(6) 0.2037(3) 0.0400(17) Uani 1 1 d . . . H15 H 0.0522 1.1092 0.1707 0.048 Uiso 1 1 calc R . . C16 C 0.0297(3) 0.2978(5) 0.2035(3) 0.0459(19) Uani 1 1 d . . . H16 H 0.0508 0.3445 0.1699 0.055 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85939(9) 0.2500 0.0407(5) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59284(9) 0.2500 0.0425(5) Uani 1 2 d S . . N1 N 0.0000 1.0837(6) 0.2500 0.035(3) Uani 1 2 d S . . N2 N 0.0000 0.3700(6) 0.2500 0.039(3) Uani 1 2 d S . . O1 O 0.0916(2) 0.8443(4) 0.2137(2) 0.0501(15) Uani 1 1 d . . . O2 O 0.0972(3) 0.6157(4) 0.2251(3) 0.0548(15) Uani 1 1 d . . . O3 O 0.0550(3) 0.8366(4) 0.3452(2) 0.0495(15) Uani 1 1 d . . . O4 O 0.0426(3) 0.6083(4) 0.3477(2) 0.0548(15) Uani 1 1 d . . . C1S C 0.0733(6) 0.8059(10) 0.0126(5) 0.186(5) Uani 1 1 d D . . H1S H 0.066(5) 0.877(7) 0.045(4) 0.279 Uiso 1 1 d D . . H2S H 0.1246(12) 0.791(10) 0.014(5) 0.279 Uiso 1 1 d D . . H3S H 0.051(5) 0.722(6) 0.025(5) 0.279 Uiso 1 1 d D . . H4S H 0.052(5) 0.834(9) -0.034(2) 0.279 Uiso 1 1 d 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 C1 0.040(4) 0.037(3) 0.041(4) 0.000(3) 0.006(3) -0.003(4) C2 0.038(4) 0.043(3) 0.050(4) -0.001(3) 0.012(3) 0.006(4) C3 0.046(6) 0.058(5) 0.098(7) 0.016(4) 0.031(5) 0.003(4) C4 0.051(7) 0.096(7) 0.115(9) 0.031(6) 0.028(6) 0.000(5) C5 0.045(5) 0.117(7) 0.085(6) -0.004(6) 0.013(5) 0.015(6) C6 0.043(7) 0.082(6) 0.098(8) -0.014(5) -0.006(6) 0.021(5) C7 0.047(6) 0.052(5) 0.077(7) -0.012(4) 0.006(5) 0.009(4) C8 0.051(5) 0.048(4) 0.054(5) -0.007(5) 0.015(4) -0.002(4) C9 0.055(5) 0.054(4) 0.036(5) -0.002(4) 0.001(4) 0.002(4) C10 0.088(7) 0.065(5) 0.049(6) -0.010(4) -0.007(6) -0.010(5) C11 0.117(9) 0.099(7) 0.057(8) -0.025(6) -0.022(7) -0.013(6) C12 0.108(8) 0.132(8) 0.050(6) 0.005(7) -0.022(6) 0.016(8) C13 0.146(11) 0.101(7) 0.071(9) 0.013(7) -0.017(8) 0.000(7) C14 0.106(8) 0.057(5) 0.065(7) 0.009(5) -0.002(6) -0.003(5) C15 0.058(5) 0.026(4) 0.039(5) -0.003(3) 0.015(4) 0.002(3) C16 0.062(5) 0.020(4) 0.061(5) 0.003(3) 0.026(4) 0.000(3) Cu1 0.0540(11) 0.0109(6) 0.0585(12) 0.000 0.0128(9) 0.000 Cu2 0.0580(12) 0.0121(6) 0.0571(12) 0.000 0.0087(9) 0.000 N1 0.035(6) 0.011(3) 0.062(7) 0.000 0.016(5) 0.000 N2 0.051(7) 0.016(4) 0.051(7) 0.000 0.007(6) 0.000 O1 0.052(4) 0.027(2) 0.078(4) 0.004(2) 0.028(3) 0.012(2) O2 0.056(4) 0.024(2) 0.089(4) 0.001(2) 0.026(3) -0.004(2) O3 0.066(4) 0.029(2) 0.051(4) 0.007(2) 0.005(3) -0.003(2) O4 0.076(4) 0.031(2) 0.056(4) -0.002(2) 0.007(3) -0.005(2) C1S 0.202(13) 0.198(11) 0.170(12) -0.021(9) 0.068(10) -0.048(10) _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 C1 O1 1.262(6) . ? C1 O2 1.263(6) . ? C1 C2 1.486(8) . ? C2 C7 1.375(8) . ? C2 C3 1.380(8) . ? C3 C4 1.365(9) . ? C4 C5 1.361(9) . ? C5 C6 1.356(9) . ? C6 C7 1.387(9) . ? C8 O3 1.265(7) . ? C8 O4 1.283(7) . ? C8 C9 1.461(8) . ? C9 C14 1.384(8) . ? C9 C10 1.384(8) . ? C10 C11 1.366(11) . ? C11 C12 1.355(11) . ? C12 C13 1.365(10) . ? C13 C14 1.345(11) . ? C15 N1 1.332(6) . ? C15 C16 1.380(6) 1_565 ? C16 N2 1.329(6) . ? C16 C15 1.380(6) 1_545 ? Cu1 O1 1.952(4) 2 ? Cu1 O1 1.952(4) . ? Cu1 O3 1.970(5) . ? Cu1 O3 1.970(5) 2 ? Cu1 N1 2.178(6) . ? Cu1 Cu2 2.5885(12) . ? Cu2 O4 1.935(5) . ? Cu2 O4 1.935(5) 2 ? Cu2 O2 1.957(4) 2 ? Cu2 O2 1.957(4) . ? Cu2 N2 2.164(6) . ? N1 C15 1.332(6) 2 ? N2 C16 1.329(6) 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 O1 C1 O2 124.3(5) . . ? O1 C1 C2 117.6(5) . . ? O2 C1 C2 118.1(6) . . ? C7 C2 C3 118.9(6) . . ? C7 C2 C1 120.2(7) . . ? C3 C2 C1 120.9(6) . . ? C4 C3 C2 120.6(7) . . ? C5 C4 C3 120.0(8) . . ? C6 C5 C4 120.6(7) . . ? C5 C6 C7 119.9(7) . . ? C2 C7 C6 120.0(7) . . ? O3 C8 O4 122.2(6) . . ? O3 C8 C9 119.8(6) . . ? O4 C8 C9 118.0(6) . . ? C14 C9 C10 117.4(7) . . ? C14 C9 C8 121.7(8) . . ? C10 C9 C8 120.9(7) . . ? C11 C10 C9 120.0(7) . . ? C12 C11 C10 121.5(8) . . ? C11 C12 C13 118.8(9) . . ? C14 C13 C12 120.7(9) . . ? C13 C14 C9 121.5(8) . . ? N1 C15 C16 121.5(7) . 1_565 ? N2 C16 C15 122.0(7) . 1_545 ? O1 Cu1 O1 171.4(2) 2 . ? O1 Cu1 O3 90.33(19) 2 . ? O1 Cu1 O3 88.70(19) . . ? O1 Cu1 O3 88.70(19) 2 2 ? O1 Cu1 O3 90.33(19) . 2 ? O3 Cu1 O3 167.1(2) . 2 ? O1 Cu1 N1 94.31(11) 2 . ? O1 Cu1 N1 94.31(11) . . ? O3 Cu1 N1 96.46(11) . . ? O3 Cu1 N1 96.46(11) 2 . ? O1 Cu1 Cu2 85.69(11) 2 . ? O1 Cu1 Cu2 85.69(11) . . ? O3 Cu1 Cu2 83.54(11) . . ? O3 Cu1 Cu2 83.54(11) 2 . ? N1 Cu1 Cu2 180.000(1) . . ? O4 Cu2 O4 171.1(2) . 2 ? O4 Cu2 O2 89.9(2) . 2 ? O4 Cu2 O2 89.1(2) 2 2 ? O4 Cu2 O2 89.1(2) . . ? O4 Cu2 O2 89.9(2) 2 . ? O2 Cu2 O2 167.0(2) 2 . ? O4 Cu2 N2 94.44(11) . . ? O4 Cu2 N2 94.44(11) 2 . ? O2 Cu2 N2 96.51(11) 2 . ? O2 Cu2 N2 96.51(11) . . ? O4 Cu2 Cu1 85.56(11) . . ? O4 Cu2 Cu1 85.56(11) 2 . ? O2 Cu2 Cu1 83.49(11) 2 . ? O2 Cu2 Cu1 83.49(11) . . ? N2 Cu2 Cu1 180.000(1) . . ? C15 N1 C15 116.7(7) 2 . ? C15 N1 Cu1 121.7(3) 2 . ? C15 N1 Cu1 121.7(3) . . ? C16 N2 C16 116.4(7) . 2 ? C16 N2 Cu2 121.8(4) . . ? C16 N2 Cu2 121.8(4) 2 . ? C1 O1 Cu1 121.5(4) . . ? C1 O2 Cu2 124.0(4) . . ? C8 O3 Cu1 124.4(4) . . ? C8 O4 Cu2 123.3(4) . . ? 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 C7 174.2(6) . . . . ? O2 C1 C2 C7 -6.7(9) . . . . ? O1 C1 C2 C3 -4.7(9) . . . . ? O2 C1 C2 C3 174.4(6) . . . . ? C7 C2 C3 C4 2.3(12) . . . . ? C1 C2 C3 C4 -178.7(8) . . . . ? C2 C3 C4 C5 0.3(15) . . . . ? C3 C4 C5 C6 -3.0(14) . . . . ? C4 C5 C6 C7 3.0(13) . . . . ? C3 C2 C7 C6 -2.3(11) . . . . ? C1 C2 C7 C6 178.7(7) . . . . ? C5 C6 C7 C2 -0.3(13) . . . . ? O3 C8 C9 C14 170.1(6) . . . . ? O4 C8 C9 C14 -11.9(10) . . . . ? O3 C8 C9 C10 -8.5(10) . . . . ? O4 C8 C9 C10 169.5(6) . . . . ? C14 C9 C10 C11 0.5(12) . . . . ? C8 C9 C10 C11 179.2(7) . . . . ? C9 C10 C11 C12 -0.5(14) . . . . ? C10 C11 C12 C13 -0.6(15) . . . . ? C11 C12 C13 C14 1.7(16) . . . . ? C12 C13 C14 C9 -1.8(16) . . . . ? C10 C9 C14 C13 0.7(13) . . . . ? C8 C9 C14 C13 -178.0(8) . . . . ? O1 Cu1 Cu2 O4 -83.7(2) 2 . . . ? O1 Cu1 Cu2 O4 96.3(2) . . . . ? O3 Cu1 Cu2 O4 7.2(2) . . . . ? O3 Cu1 Cu2 O4 -172.8(2) 2 . . . ? N1 Cu1 Cu2 O4 75(64) . . . . ? O1 Cu1 Cu2 O4 96.3(2) 2 . . 2 ? O1 Cu1 Cu2 O4 -83.7(2) . . . 2 ? O3 Cu1 Cu2 O4 -172.8(2) . . . 2 ? O3 Cu1 Cu2 O4 7.2(2) 2 . . 2 ? N1 Cu1 Cu2 O4 -105(61) . . . 2 ? O1 Cu1 Cu2 O2 6.7(2) 2 . . 2 ? O1 Cu1 Cu2 O2 -173.3(2) . . . 2 ? O3 Cu1 Cu2 O2 97.5(2) . . . 2 ? O3 Cu1 Cu2 O2 -82.5(2) 2 . . 2 ? N1 Cu1 Cu2 O2 166(64) . . . 2 ? O1 Cu1 Cu2 O2 -173.3(2) 2 . . . ? O1 Cu1 Cu2 O2 6.7(2) . . . . ? O3 Cu1 Cu2 O2 -82.5(2) . . . . ? O3 Cu1 Cu2 O2 97.5(2) 2 . . . ? N1 Cu1 Cu2 O2 -14(61) . . . . ? O1 Cu1 Cu2 N2 21(100) 2 . . . ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O3 Cu1 Cu2 N2 112(100) . . . . ? O3 Cu1 Cu2 N2 -68(100) 2 . . . ? N1 Cu1 Cu2 N2 0(63) . . . . ? C16 C15 N1 C15 -0.4(5) 1_565 . . 2 ? C16 C15 N1 Cu1 179.6(5) 1_565 . . . ? O1 Cu1 N1 C15 30.5(3) 2 . . 2 ? O1 Cu1 N1 C15 -149.5(3) . . . 2 ? O3 Cu1 N1 C15 -60.4(3) . . . 2 ? O3 Cu1 N1 C15 119.6(3) 2 . . 2 ? Cu2 Cu1 N1 C15 -129(65) . . . 2 ? O1 Cu1 N1 C15 -149.5(3) 2 . . . ? O1 Cu1 N1 C15 30.5(3) . . . . ? O3 Cu1 N1 C15 119.6(3) . . . . ? O3 Cu1 N1 C15 -60.4(3) 2 . . . ? Cu2 Cu1 N1 C15 51(61) . . . . ? C15 C16 N2 C16 -0.4(5) 1_545 . . 2 ? C15 C16 N2 Cu2 179.6(5) 1_545 . . . ? O4 Cu2 N2 C16 -127.3(3) . . . . ? O4 Cu2 N2 C16 52.7(3) 2 . . . ? O2 Cu2 N2 C16 142.4(3) 2 . . . ? O2 Cu2 N2 C16 -37.6(3) . . . . ? Cu1 Cu2 N2 C16 128(100) . . . . ? O4 Cu2 N2 C16 52.7(3) . . . 2 ? O4 Cu2 N2 C16 -127.3(3) 2 . . 2 ? O2 Cu2 N2 C16 -37.6(3) 2 . . 2 ? O2 Cu2 N2 C16 142.4(3) . . . 2 ? Cu1 Cu2 N2 C16 -52(100) . . . 2 ? O2 C1 O1 Cu1 8.1(8) . . . . ? C2 C1 O1 Cu1 -172.9(4) . . . . ? O1 Cu1 O1 C1 -9.6(5) 2 . . . ? O3 Cu1 O1 C1 74.0(5) . . . . ? O3 Cu1 O1 C1 -93.1(5) 2 . . . ? N1 Cu1 O1 C1 170.4(5) . . . . ? Cu2 Cu1 O1 C1 -9.6(5) . . . . ? O1 C1 O2 Cu2 1.1(8) . . . . ? C2 C1 O2 Cu2 -177.9(4) . . . . ? O4 Cu2 O2 C1 -92.0(5) . . . . ? O4 Cu2 O2 C1 79.1(5) 2 . . . ? O2 Cu2 O2 C1 -6.4(5) 2 . . . ? N2 Cu2 O2 C1 173.6(5) . . . . ? Cu1 Cu2 O2 C1 -6.4(5) . . . . ? O4 C8 O3 Cu1 3.6(8) . . . . ? C9 C8 O3 Cu1 -178.5(4) . . . . ? O1 Cu1 O3 C8 77.6(5) 2 . . . ? O1 Cu1 O3 C8 -93.8(5) . . . . ? O3 Cu1 O3 C8 -8.0(5) 2 . . . ? N1 Cu1 O3 C8 172.0(5) . . . . ? Cu2 Cu1 O3 C8 -8.0(5) . . . . ? O3 C8 O4 Cu2 6.3(8) . . . . ? C9 C8 O4 Cu2 -171.6(4) . . . . ? O4 Cu2 O4 C8 -9.3(5) 2 . . . ? O2 Cu2 O4 C8 -92.8(5) 2 . . . ? O2 Cu2 O4 C8 74.2(5) . . . . ? N2 Cu2 O4 C8 170.7(5) . . . . ? Cu1 Cu2 O4 C8 -9.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.533 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.071 #===END data_311221 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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 C2/c 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 18.589(3) _cell_length_b 9.7134(14) _cell_length_c 19.335(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.338(3) _cell_angle_gamma 90.00 _cell_volume 3444.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 270 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.285 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5126 _exptl_absorpt_correction_T_max 0.8610 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; sample sealed at 298 K with 19 MPa ; _diffrn_ambient_temperature 270 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12524 _diffrn_reflns_av_R_equivalents 0.1231 _diffrn_reflns_av_sigmaI/netI 0.1495 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4250 _reflns_number_gt 1746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0334P)^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 4250 _refine_ls_number_parameters 222 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1738 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_restrained_S_all 0.882 _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 C1 C 0.1237(3) 0.7303(5) 0.2113(2) 0.0389(11) Uani 1 1 d . . . C2 C 0.1978(3) 0.7318(4) 0.1917(2) 0.0399(11) Uani 1 1 d . . . C3 C 0.2275(3) 0.8517(5) 0.1701(3) 0.0614(16) Uani 1 1 d . . . H3 H 0.2012 0.9334 0.1689 0.074 Uiso 1 1 calc R . . C4 C 0.2954(4) 0.8518(6) 0.1504(3) 0.081(2) Uani 1 1 d . . . H4 H 0.3151 0.9334 0.1365 0.097 Uiso 1 1 calc R . . C5 C 0.3337(3) 0.7314(7) 0.1511(3) 0.0761(17) Uani 1 1 d . . . H5 H 0.3789 0.7305 0.1365 0.091 Uiso 1 1 calc R . . C6 C 0.3056(3) 0.6128(6) 0.1734(3) 0.0706(18) Uani 1 1 d . . . H6 H 0.3324 0.5317 0.1748 0.085 Uiso 1 1 calc R . . C7 C 0.2383(3) 0.6122(5) 0.1938(3) 0.0514(15) Uani 1 1 d . . . H7 H 0.2198 0.5307 0.2092 0.062 Uiso 1 1 calc R . . C8 C 0.0649(3) 0.7219(5) 0.3756(2) 0.0440(12) Uani 1 1 d . . . C9 C 0.1052(3) 0.7188(5) 0.4484(2) 0.0488(13) Uani 1 1 d . . . C10 C 0.1413(3) 0.8332(5) 0.4783(3) 0.0697(18) Uani 1 1 d . . . H10 H 0.1406 0.9143 0.4526 0.084 Uiso 1 1 calc R . . C11 C 0.1787(4) 0.8285(7) 0.5465(4) 0.089(2) Uani 1 1 d . . . H11 H 0.2029 0.9064 0.5663 0.107 Uiso 1 1 calc R . . C12 C 0.1801(4) 0.7106(8) 0.5845(3) 0.093(2) Uani 1 1 d . . . H12 H 0.2053 0.7071 0.6301 0.111 Uiso 1 1 calc R . . C13 C 0.1436(4) 0.5958(7) 0.5546(4) 0.093(2) Uani 1 1 d . . . H13 H 0.1437 0.5150 0.5805 0.112 Uiso 1 1 calc R . . C14 C 0.1075(3) 0.6009(5) 0.4875(3) 0.0718(18) Uani 1 1 d . . . H14 H 0.0839 0.5224 0.4678 0.086 Uiso 1 1 calc R . . C15 C 0.0304(2) 1.1546(4) 0.2036(2) 0.0403(12) Uani 1 1 d . . . H15 H 0.0521 1.1075 0.1705 0.048 Uiso 1 1 calc R . . C16 C 0.0304(2) 0.2976(4) 0.2034(2) 0.0400(12) Uani 1 1 d . . . H16 H 0.0520 0.3444 0.1701 0.048 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85936(6) 0.2500 0.0380(3) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59288(6) 0.2500 0.0402(3) Uani 1 2 d S . . N1 N 0.0000 1.0841(4) 0.2500 0.0320(14) Uani 1 2 d S . . N2 N 0.0000 0.3691(4) 0.2500 0.0339(15) Uani 1 2 d S . . O1 O 0.09153(17) 0.8446(3) 0.21322(17) 0.0458(9) Uani 1 1 d . . . O2 O 0.09749(18) 0.6156(3) 0.22533(17) 0.0488(10) Uani 1 1 d . . . O3 O 0.05561(18) 0.8373(3) 0.34525(16) 0.0470(9) Uani 1 1 d . . . O4 O 0.04247(19) 0.6081(3) 0.34833(16) 0.0500(10) Uani 1 1 d . . . C1S C 0.0734(4) 0.8076(7) 0.0128(3) 0.151(3) Uani 1 1 d D . . H1S H 0.049(3) 0.849(6) -0.0294(19) 0.227 Uiso 1 1 d D . . H2S H 0.063(4) 0.858(5) 0.053(2) 0.227 Uiso 1 1 d D . . H3S H 0.057(4) 0.714(2) 0.015(3) 0.227 Uiso 1 1 d D . . H4S H 0.1249(7) 0.809(7) 0.012(3) 0.227 Uiso 1 1 d 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 C1 0.046(3) 0.038(2) 0.032(3) 0.000(2) 0.005(2) 0.000(3) C2 0.038(3) 0.039(2) 0.043(3) -0.001(2) 0.007(3) 0.003(2) C3 0.048(4) 0.055(3) 0.082(4) 0.019(3) 0.013(4) 0.001(3) C4 0.053(5) 0.092(5) 0.103(6) 0.022(4) 0.028(4) -0.005(4) C5 0.034(3) 0.121(5) 0.074(4) -0.006(4) 0.011(3) 0.003(4) C6 0.042(4) 0.078(4) 0.090(5) -0.017(4) 0.005(4) 0.013(3) C7 0.040(4) 0.051(3) 0.062(4) -0.010(3) 0.007(3) 0.004(3) C8 0.040(3) 0.048(3) 0.045(3) -0.003(3) 0.012(3) 0.004(3) C9 0.051(3) 0.049(3) 0.045(3) 0.000(3) 0.007(3) 0.002(3) C10 0.092(5) 0.058(3) 0.057(4) -0.005(3) 0.006(4) -0.011(3) C11 0.096(6) 0.088(5) 0.075(5) -0.023(4) -0.009(5) -0.010(4) C12 0.097(6) 0.121(6) 0.054(4) -0.002(5) -0.009(4) 0.013(5) C13 0.117(7) 0.085(5) 0.071(5) 0.021(4) -0.003(5) 0.005(5) C14 0.092(5) 0.067(4) 0.049(4) 0.008(3) -0.009(4) 0.002(3) C15 0.053(4) 0.024(3) 0.048(3) -0.001(2) 0.019(3) 0.005(2) C16 0.048(3) 0.027(3) 0.048(3) 0.007(2) 0.020(3) 0.004(2) Cu1 0.0462(7) 0.0153(4) 0.0535(7) 0.000 0.0114(6) 0.000 Cu2 0.0522(7) 0.0147(4) 0.0536(7) 0.000 0.0081(6) 0.000 N1 0.034(4) 0.023(3) 0.039(4) 0.000 0.007(3) 0.000 N2 0.035(4) 0.020(3) 0.046(4) 0.000 0.006(3) 0.000 O1 0.048(2) 0.0251(17) 0.069(2) 0.0029(15) 0.024(2) 0.0065(15) O2 0.051(3) 0.0275(17) 0.073(3) -0.0012(15) 0.024(2) -0.0021(15) O3 0.061(3) 0.0304(17) 0.049(2) 0.0051(15) 0.007(2) -0.0019(16) O4 0.076(3) 0.0265(17) 0.044(2) 0.0007(14) 0.000(2) -0.0041(16) C1S 0.161(8) 0.179(8) 0.120(7) -0.017(6) 0.043(6) -0.046(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 C1 O2 1.263(5) . ? C1 O1 1.264(5) . ? C1 C2 1.488(6) . ? C2 C7 1.381(6) . ? C2 C3 1.382(6) . ? C3 C4 1.376(7) . ? C4 C5 1.368(7) . ? C5 C6 1.362(7) . ? C6 C7 1.373(6) . ? C8 O3 1.264(5) . ? C8 O4 1.266(5) . ? C8 C9 1.484(6) . ? C9 C14 1.369(6) . ? C9 C10 1.375(6) . ? C10 C11 1.389(7) . ? C11 C12 1.358(8) . ? C12 C13 1.381(7) . ? C13 C14 1.362(8) . ? C15 N1 1.327(4) . ? C15 C16 1.389(5) 1_565 ? C16 N2 1.334(4) . ? C16 C15 1.389(5) 1_545 ? Cu1 O1 1.953(3) 2 ? Cu1 O1 1.953(3) . ? Cu1 O3 1.972(3) 2 ? Cu1 O3 1.972(3) . ? Cu1 N1 2.183(4) . ? Cu1 Cu2 2.5884(9) . ? Cu2 O4 1.942(3) . ? Cu2 O4 1.942(3) 2 ? Cu2 O2 1.960(3) . ? Cu2 O2 1.960(3) 2 ? Cu2 N2 2.174(4) . ? N1 C15 1.327(4) 2 ? N2 C16 1.334(4) 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 C1 O1 124.6(4) . . ? O2 C1 C2 117.9(4) . . ? O1 C1 C2 117.5(4) . . ? C7 C2 C3 118.5(5) . . ? C7 C2 C1 120.4(4) . . ? C3 C2 C1 121.1(4) . . ? C4 C3 C2 120.9(5) . . ? C5 C4 C3 119.7(5) . . ? C6 C5 C4 120.1(5) . . ? C5 C6 C7 120.6(5) . . ? C6 C7 C2 120.3(5) . . ? O3 C8 O4 124.7(4) . . ? O3 C8 C9 117.9(4) . . ? O4 C8 C9 117.4(4) . . ? C14 C9 C10 118.4(5) . . ? C14 C9 C8 120.4(5) . . ? C10 C9 C8 121.3(5) . . ? C9 C10 C11 120.5(5) . . ? C12 C11 C10 120.2(6) . . ? C11 C12 C13 119.4(6) . . ? C14 C13 C12 120.1(6) . . ? C13 C14 C9 121.5(6) . . ? N1 C15 C16 121.2(4) . 1_565 ? N2 C16 C15 121.2(4) . 1_545 ? O1 Cu1 O1 171.57(16) 2 . ? O1 Cu1 O3 88.65(13) 2 2 ? O1 Cu1 O3 90.43(14) . 2 ? O1 Cu1 O3 90.43(13) 2 . ? O1 Cu1 O3 88.65(13) . . ? O3 Cu1 O3 167.52(17) 2 . ? O1 Cu1 N1 94.21(8) 2 . ? O1 Cu1 N1 94.21(8) . . ? O3 Cu1 N1 96.24(8) 2 . ? O3 Cu1 N1 96.24(8) . . ? O1 Cu1 Cu2 85.79(8) 2 . ? O1 Cu1 Cu2 85.79(8) . . ? O3 Cu1 Cu2 83.76(8) 2 . ? O3 Cu1 Cu2 83.76(8) . . ? N1 Cu1 Cu2 180.000(1) . . ? O4 Cu2 O4 171.25(16) . 2 ? O4 Cu2 O2 89.12(14) . . ? O4 Cu2 O2 89.89(14) 2 . ? O4 Cu2 O2 89.89(14) . 2 ? O4 Cu2 O2 89.12(14) 2 2 ? O2 Cu2 O2 167.05(16) . 2 ? O4 Cu2 N2 94.37(8) . . ? O4 Cu2 N2 94.37(8) 2 . ? O2 Cu2 N2 96.47(8) . . ? O2 Cu2 N2 96.47(8) 2 . ? O4 Cu2 Cu1 85.63(8) . . ? O4 Cu2 Cu1 85.63(8) 2 . ? O2 Cu2 Cu1 83.53(8) . . ? O2 Cu2 Cu1 83.53(8) 2 . ? N2 Cu2 Cu1 180.0 . . ? C15 N1 C15 117.8(5) 2 . ? C15 N1 Cu1 121.1(3) 2 . ? C15 N1 Cu1 121.1(3) . . ? C16 N2 C16 117.3(5) 2 . ? C16 N2 Cu2 121.3(2) 2 . ? C16 N2 Cu2 121.3(2) . . ? C1 O1 Cu1 121.3(3) . . ? C1 O2 Cu2 123.8(3) . . ? C8 O3 Cu1 122.8(3) . . ? C8 O4 Cu2 121.9(3) . . ? 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 O2 C1 C2 C7 -4.5(7) . . . . ? O1 C1 C2 C7 174.9(4) . . . . ? O2 C1 C2 C3 174.7(4) . . . . ? O1 C1 C2 C3 -5.9(7) . . . . ? C7 C2 C3 C4 0.8(8) . . . . ? C1 C2 C3 C4 -178.4(5) . . . . ? C2 C3 C4 C5 0.9(10) . . . . ? C3 C4 C5 C6 -2.0(10) . . . . ? C4 C5 C6 C7 1.4(9) . . . . ? C5 C6 C7 C2 0.4(9) . . . . ? C3 C2 C7 C6 -1.4(8) . . . . ? C1 C2 C7 C6 177.8(5) . . . . ? O3 C8 C9 C14 170.2(5) . . . . ? O4 C8 C9 C14 -10.2(7) . . . . ? O3 C8 C9 C10 -9.9(7) . . . . ? O4 C8 C9 C10 169.7(4) . . . . ? C14 C9 C10 C11 -0.2(9) . . . . ? C8 C9 C10 C11 179.9(5) . . . . ? C9 C10 C11 C12 0.0(10) . . . . ? C10 C11 C12 C13 -0.3(11) . . . . ? C11 C12 C13 C14 0.9(11) . . . . ? C12 C13 C14 C9 -1.1(10) . . . . ? C10 C9 C14 C13 0.8(9) . . . . ? C8 C9 C14 C13 -179.3(5) . . . . ? O1 Cu1 Cu2 O4 -83.26(15) 2 . . . ? O1 Cu1 Cu2 O4 96.74(15) . . . . ? O3 Cu1 Cu2 O4 -172.36(15) 2 . . . ? O3 Cu1 Cu2 O4 7.64(15) . . . . ? N1 Cu1 Cu2 O4 76(48) . . . . ? O1 Cu1 Cu2 O4 96.74(15) 2 . . 2 ? O1 Cu1 Cu2 O4 -83.26(15) . . . 2 ? O3 Cu1 Cu2 O4 7.64(15) 2 . . 2 ? O3 Cu1 Cu2 O4 -172.36(15) . . . 2 ? N1 Cu1 Cu2 O4 -104(46) . . . 2 ? O1 Cu1 Cu2 O2 -172.87(15) 2 . . . ? O1 Cu1 Cu2 O2 7.13(15) . . . . ? O3 Cu1 Cu2 O2 98.03(14) 2 . . . ? O3 Cu1 Cu2 O2 -81.97(14) . . . . ? N1 Cu1 Cu2 O2 -14(46) . . . . ? O1 Cu1 Cu2 O2 7.13(15) 2 . . 2 ? O1 Cu1 Cu2 O2 -172.87(15) . . . 2 ? O3 Cu1 Cu2 O2 -81.97(14) 2 . . 2 ? O3 Cu1 Cu2 O2 98.03(14) . . . 2 ? N1 Cu1 Cu2 O2 166(48) . . . 2 ? O1 Cu1 Cu2 N2 21(100) 2 . . . ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O3 Cu1 Cu2 N2 -68(100) 2 . . . ? O3 Cu1 Cu2 N2 112(100) . . . . ? N1 Cu1 Cu2 N2 0(47) . . . . ? C16 C15 N1 C15 -0.1(3) 1_565 . . 2 ? C16 C15 N1 Cu1 179.9(3) 1_565 . . . ? O1 Cu1 N1 C15 30.1(2) 2 . . 2 ? O1 Cu1 N1 C15 -149.9(2) . . . 2 ? O3 Cu1 N1 C15 119.2(2) 2 . . 2 ? O3 Cu1 N1 C15 -60.8(2) . . . 2 ? Cu2 Cu1 N1 C15 -129(48) . . . 2 ? O1 Cu1 N1 C15 -149.9(2) 2 . . . ? O1 Cu1 N1 C15 30.1(2) . . . . ? O3 Cu1 N1 C15 -60.8(2) 2 . . . ? O3 Cu1 N1 C15 119.2(2) . . . . ? Cu2 Cu1 N1 C15 51(46) . . . . ? C15 C16 N2 C16 -0.1(3) 1_545 . . 2 ? C15 C16 N2 Cu2 179.9(3) 1_545 . . . ? O4 Cu2 N2 C16 53.0(2) . . . 2 ? O4 Cu2 N2 C16 -127.0(2) 2 . . 2 ? O2 Cu2 N2 C16 142.6(2) . . . 2 ? O2 Cu2 N2 C16 -37.4(2) 2 . . 2 ? Cu1 Cu2 N2 C16 -51(100) . . . 2 ? O4 Cu2 N2 C16 -127.0(2) . . . . ? O4 Cu2 N2 C16 53.0(2) 2 . . . ? O2 Cu2 N2 C16 -37.4(2) . . . . ? O2 Cu2 N2 C16 142.6(2) 2 . . . ? Cu1 Cu2 N2 C16 129(100) . . . . ? O2 C1 O1 Cu1 7.6(6) . . . . ? C2 C1 O1 Cu1 -171.8(3) . . . . ? O1 Cu1 O1 C1 -9.7(3) 2 . . . ? O3 Cu1 O1 C1 -93.4(3) 2 . . . ? O3 Cu1 O1 C1 74.1(3) . . . . ? N1 Cu1 O1 C1 170.3(3) . . . . ? Cu2 Cu1 O1 C1 -9.7(3) . . . . ? O1 C1 O2 Cu2 2.1(6) . . . . ? C2 C1 O2 Cu2 -178.5(3) . . . . ? O4 Cu2 O2 C1 -92.9(3) . . . . ? O4 Cu2 O2 C1 78.4(3) 2 . . . ? O2 Cu2 O2 C1 -7.2(3) 2 . . . ? N2 Cu2 O2 C1 172.8(3) . . . . ? Cu1 Cu2 O2 C1 -7.2(3) . . . . ? O4 C8 O3 Cu1 2.8(6) . . . . ? C9 C8 O3 Cu1 -177.6(3) . . . . ? O1 Cu1 O3 C8 77.8(4) 2 . . . ? O1 Cu1 O3 C8 -93.8(3) . . . . ? O3 Cu1 O3 C8 -7.9(3) 2 . . . ? N1 Cu1 O3 C8 172.1(3) . . . . ? Cu2 Cu1 O3 C8 -7.9(3) . . . . ? O3 C8 O4 Cu2 7.6(6) . . . . ? C9 C8 O4 Cu2 -172.0(3) . . . . ? O4 Cu2 O4 C8 -10.2(3) 2 . . . ? O2 Cu2 O4 C8 73.3(4) . . . . ? O2 Cu2 O4 C8 -93.8(4) 2 . . . ? N2 Cu2 O4 C8 169.8(3) . . . . ? Cu1 Cu2 O4 C8 -10.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.599 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.081 #===END data_311211 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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 C2/c 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 18.550(3) _cell_length_b 9.7068(15) _cell_length_c 19.311(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.297(3) _cell_angle_gamma 90.00 _cell_volume 3431.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 240 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.290 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5115 _exptl_absorpt_correction_T_max 0.8605 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; sample sealed at 298 K with 19 MPa CH4 ; _diffrn_ambient_temperature 240 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12453 _diffrn_reflns_av_R_equivalents 0.1218 _diffrn_reflns_av_sigmaI/netI 0.1477 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4236 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0309P)^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 4236 _refine_ls_number_parameters 222 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1639 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.892 _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 C1 C 0.1241(3) 0.7300(4) -0.7887(2) 0.0349(11) Uani 1 1 d . . . C2 C 0.1983(3) 0.7321(4) -0.8081(2) 0.0366(11) Uani 1 1 d . . . C3 C 0.2277(3) 0.8524(5) -0.8295(3) 0.0561(16) Uani 1 1 d . . . H3 H 0.2015 0.9353 -0.8297 0.067 Uiso 1 1 calc R . . C4 C 0.2952(4) 0.8524(6) -0.8507(3) 0.0735(19) Uani 1 1 d . . . H4 H 0.3146 0.9344 -0.8660 0.088 Uiso 1 1 calc R . . C5 C 0.3338(3) 0.7318(7) -0.8493(3) 0.0681(16) Uani 1 1 d . . . H5 H 0.3796 0.7313 -0.8643 0.082 Uiso 1 1 calc R . . C6 C 0.3065(3) 0.6121(6) -0.8265(3) 0.0626(17) Uani 1 1 d . . . H6 H 0.3339 0.5303 -0.8247 0.075 Uiso 1 1 calc R . . C7 C 0.2390(3) 0.6124(5) -0.8063(3) 0.0491(15) Uani 1 1 d . . . H7 H 0.2202 0.5301 -0.7909 0.059 Uiso 1 1 calc R . . C8 C 0.0654(2) 0.7218(5) -0.6242(2) 0.0389(11) Uani 1 1 d . . . C9 C 0.1060(3) 0.7185(5) -0.5504(2) 0.0412(12) Uani 1 1 d . . . C10 C 0.1413(3) 0.8331(5) -0.5213(3) 0.0603(17) Uani 1 1 d . . . H10 H 0.1399 0.9150 -0.5475 0.072 Uiso 1 1 calc R . . C11 C 0.1788(4) 0.8290(6) -0.4538(4) 0.079(2) Uani 1 1 d . . . H11 H 0.2035 0.9081 -0.4345 0.095 Uiso 1 1 calc R . . C12 C 0.1808(4) 0.7124(8) -0.4148(3) 0.0822(19) Uani 1 1 d . . . H12 H 0.2065 0.7100 -0.3687 0.099 Uiso 1 1 calc R . . C13 C 0.1447(4) 0.5988(6) -0.4440(3) 0.082(2) Uani 1 1 d . . . H13 H 0.1452 0.5178 -0.4172 0.098 Uiso 1 1 calc R . . C14 C 0.1078(3) 0.5997(5) -0.5113(3) 0.0624(17) Uani 1 1 d . . . H14 H 0.0839 0.5199 -0.5307 0.075 Uiso 1 1 calc R . . C15 C 0.0306(2) 1.1548(4) -0.7962(2) 0.0327(11) Uani 1 1 d . . . H15 H 0.0528 1.1070 -0.8295 0.039 Uiso 1 1 calc R . . C16 C 0.0307(2) 0.2984(4) -0.7965(2) 0.0367(12) Uani 1 1 d . . . H16 H 0.0527 0.3460 -0.8300 0.044 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.85929(6) -0.7500 0.0339(3) Uani 1 2 d S . . Cu2 Cu 0.0000 0.59281(6) -0.7500 0.0363(3) Uani 1 2 d S . . N1 N 0.0000 1.0842(4) -0.7500 0.0287(14) Uani 1 2 d S . . N2 N 0.0000 0.3687(5) -0.7500 0.0311(14) Uani 1 2 d S . . O1 O 0.09171(17) 0.8445(3) -0.78692(16) 0.0401(9) Uani 1 1 d . . . O2 O 0.09808(18) 0.6157(3) -0.77458(17) 0.0441(9) Uani 1 1 d . . . O3 O 0.05595(18) 0.8369(3) -0.65461(15) 0.0417(9) Uani 1 1 d . . . O4 O 0.04215(19) 0.6081(3) -0.65154(16) 0.0458(10) Uani 1 1 d . . . C1S C 0.0729(4) 0.8081(7) 0.0132(3) 0.136(3) Uani 1 1 d D . . H1S H 0.050(3) 0.719(3) 0.014(3) 0.204 Uiso 1 1 d D . . H2S H 0.063(3) 0.861(5) 0.0526(19) 0.204 Uiso 1 1 d D . . H3S H 0.053(3) 0.855(5) -0.0295(16) 0.204 Uiso 1 1 d D . . H4S H 0.1247(6) 0.797(6) 0.016(3) 0.204 Uiso 1 1 d 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 C1 0.040(3) 0.029(2) 0.037(3) 0.002(2) 0.009(2) 0.000(3) C2 0.035(3) 0.037(2) 0.037(3) -0.006(2) 0.005(2) -0.004(2) C3 0.044(4) 0.052(3) 0.074(4) 0.014(3) 0.015(3) 0.003(3) C4 0.051(5) 0.084(5) 0.088(5) 0.018(4) 0.020(4) -0.002(4) C5 0.036(3) 0.108(5) 0.062(4) -0.002(4) 0.010(3) 0.007(4) C6 0.041(4) 0.070(4) 0.076(4) -0.011(3) 0.007(4) 0.015(3) C7 0.040(4) 0.045(3) 0.060(4) -0.013(2) 0.000(3) 0.005(3) C8 0.036(3) 0.040(2) 0.043(3) -0.001(3) 0.014(3) 0.003(3) C9 0.043(3) 0.045(2) 0.036(3) -0.003(3) 0.008(3) 0.004(3) C10 0.077(5) 0.047(3) 0.054(4) -0.011(3) 0.000(4) -0.006(3) C11 0.089(6) 0.074(4) 0.066(5) -0.024(4) -0.008(4) -0.014(4) C12 0.091(5) 0.109(5) 0.040(4) -0.012(4) -0.010(4) 0.013(5) C13 0.115(7) 0.075(4) 0.050(4) 0.014(3) -0.005(4) 0.011(4) C14 0.079(5) 0.054(3) 0.048(4) 0.007(3) -0.007(4) 0.000(3) C15 0.040(3) 0.020(2) 0.041(3) 0.0004(18) 0.016(3) 0.001(2) C16 0.046(3) 0.024(3) 0.044(3) 0.0052(19) 0.022(3) -0.001(2) Cu1 0.0427(6) 0.0130(4) 0.0473(6) 0.000 0.0111(5) 0.000 Cu2 0.0469(7) 0.0134(4) 0.0489(6) 0.000 0.0081(5) 0.000 N1 0.027(4) 0.018(3) 0.041(4) 0.000 0.007(3) 0.000 N2 0.034(4) 0.022(3) 0.036(4) 0.000 0.004(3) 0.000 O1 0.041(2) 0.0252(17) 0.059(2) 0.0036(14) 0.0213(19) 0.0067(15) O2 0.046(2) 0.0226(17) 0.067(2) 0.0017(14) 0.019(2) -0.0028(15) O3 0.052(2) 0.0286(17) 0.042(2) 0.0006(14) -0.0002(19) -0.0014(16) O4 0.065(3) 0.0255(17) 0.045(2) 0.0013(14) 0.002(2) -0.0038(16) C1S 0.137(8) 0.158(7) 0.122(6) -0.019(5) 0.044(6) -0.054(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 C1 O2 1.257(4) . ? C1 O1 1.266(5) . ? C1 C2 1.484(6) . ? C2 C3 1.382(6) . ? C2 C7 1.383(6) . ? C3 C4 1.377(7) . ? C4 C5 1.371(7) . ? C5 C6 1.368(7) . ? C6 C7 1.370(6) . ? C8 O3 1.261(5) . ? C8 O4 1.268(5) . ? C8 C9 1.501(6) . ? C9 C10 1.364(6) . ? C9 C14 1.376(6) . ? C10 C11 1.376(7) . ? C11 C12 1.357(7) . ? C12 C13 1.364(7) . ? C13 C14 1.369(7) . ? C15 N1 1.324(4) . ? C15 C16 1.395(5) 1_565 ? C16 N2 1.327(4) . ? C16 C15 1.395(5) 1_545 ? Cu1 O1 1.953(3) 2_553 ? Cu1 O1 1.953(3) . ? Cu1 O3 1.975(3) . ? Cu1 O3 1.975(3) 2_553 ? Cu1 N1 2.183(4) . ? Cu1 Cu2 2.5867(10) . ? Cu2 O4 1.941(3) . ? Cu2 O4 1.941(3) 2_553 ? Cu2 O2 1.966(3) 2_553 ? Cu2 O2 1.966(3) . ? Cu2 N2 2.175(5) . ? N1 C15 1.324(4) 2_553 ? N2 C16 1.327(4) 2_553 ? 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 C1 O1 124.7(4) . . ? O2 C1 C2 118.1(4) . . ? O1 C1 C2 117.2(4) . . ? C3 C2 C7 118.5(5) . . ? C3 C2 C1 121.0(4) . . ? C7 C2 C1 120.5(4) . . ? C4 C3 C2 120.7(5) . . ? C5 C4 C3 119.4(6) . . ? C6 C5 C4 120.8(5) . . ? C5 C6 C7 119.5(5) . . ? C6 C7 C2 121.0(5) . . ? O3 C8 O4 124.4(4) . . ? O3 C8 C9 118.1(4) . . ? O4 C8 C9 117.5(4) . . ? C10 C9 C14 119.4(5) . . ? C10 C9 C8 120.5(5) . . ? C14 C9 C8 120.1(5) . . ? C9 C10 C11 120.1(5) . . ? C12 C11 C10 121.0(6) . . ? C11 C12 C13 118.5(6) . . ? C12 C13 C14 121.6(6) . . ? C13 C14 C9 119.4(5) . . ? N1 C15 C16 121.4(4) . 1_565 ? N2 C16 C15 120.7(4) . 1_545 ? O1 Cu1 O1 171.57(16) 2_553 . ? O1 Cu1 O3 90.51(13) 2_553 . ? O1 Cu1 O3 88.56(13) . . ? O1 Cu1 O3 88.56(13) 2_553 2_553 ? O1 Cu1 O3 90.51(13) . 2_553 ? O3 Cu1 O3 167.36(17) . 2_553 ? O1 Cu1 N1 94.22(8) 2_553 . ? O1 Cu1 N1 94.22(8) . . ? O3 Cu1 N1 96.32(8) . . ? O3 Cu1 N1 96.32(8) 2_553 . ? O1 Cu1 Cu2 85.78(8) 2_553 . ? O1 Cu1 Cu2 85.78(8) . . ? O3 Cu1 Cu2 83.68(8) . . ? O3 Cu1 Cu2 83.68(8) 2_553 . ? N1 Cu1 Cu2 180.0 . . ? O4 Cu2 O4 171.22(16) . 2_553 ? O4 Cu2 O2 89.82(14) . 2_553 ? O4 Cu2 O2 89.19(14) 2_553 2_553 ? O4 Cu2 O2 89.19(14) . . ? O4 Cu2 O2 89.82(14) 2_553 . ? O2 Cu2 O2 167.04(16) 2_553 . ? O4 Cu2 N2 94.39(8) . . ? O4 Cu2 N2 94.39(8) 2_553 . ? O2 Cu2 N2 96.48(8) 2_553 . ? O2 Cu2 N2 96.48(8) . . ? O4 Cu2 Cu1 85.61(8) . . ? O4 Cu2 Cu1 85.61(8) 2_553 . ? O2 Cu2 Cu1 83.52(8) 2_553 . ? O2 Cu2 Cu1 83.52(8) . . ? N2 Cu2 Cu1 180.000(1) . . ? C15 N1 C15 117.7(5) 2_553 . ? C15 N1 Cu1 121.2(2) 2_553 . ? C15 N1 Cu1 121.2(2) . . ? C16 N2 C16 118.2(5) 2_553 . ? C16 N2 Cu2 120.9(2) 2_553 . ? C16 N2 Cu2 120.9(3) . . ? C1 O1 Cu1 121.3(3) . . ? C1 O2 Cu2 123.7(3) . . ? C8 O3 Cu1 123.0(3) . . ? C8 O4 Cu2 122.0(3) . . ? 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 O2 C1 C2 C3 174.8(4) . . . . ? O1 C1 C2 C3 -5.8(7) . . . . ? O2 C1 C2 C7 -4.0(6) . . . . ? O1 C1 C2 C7 175.4(4) . . . . ? C7 C2 C3 C4 2.0(8) . . . . ? C1 C2 C3 C4 -176.9(5) . . . . ? C2 C3 C4 C5 -1.0(9) . . . . ? C3 C4 C5 C6 -0.7(9) . . . . ? C4 C5 C6 C7 1.5(9) . . . . ? C5 C6 C7 C2 -0.5(8) . . . . ? C3 C2 C7 C6 -1.2(7) . . . . ? C1 C2 C7 C6 177.6(5) . . . . ? O3 C8 C9 C10 -10.1(7) . . . . ? O4 C8 C9 C10 170.6(4) . . . . ? O3 C8 C9 C14 169.9(4) . . . . ? O4 C8 C9 C14 -9.4(7) . . . . ? C14 C9 C10 C11 0.6(8) . . . . ? C8 C9 C10 C11 -179.5(5) . . . . ? C9 C10 C11 C12 -0.8(10) . . . . ? C10 C11 C12 C13 0.1(10) . . . . ? C11 C12 C13 C14 0.8(10) . . . . ? C12 C13 C14 C9 -1.0(10) . . . . ? C10 C9 C14 C13 0.3(8) . . . . ? C8 C9 C14 C13 -179.7(5) . . . . ? O1 Cu1 Cu2 O4 -83.02(14) 2_553 . . . ? O1 Cu1 Cu2 O4 96.98(14) . . . . ? O3 Cu1 Cu2 O4 7.96(15) . . . . ? O3 Cu1 Cu2 O4 -172.04(15) 2_553 . . . ? N1 Cu1 Cu2 O4 76(100) . . . . ? O1 Cu1 Cu2 O4 96.98(14) 2_553 . . 2_553 ? O1 Cu1 Cu2 O4 -83.02(14) . . . 2_553 ? O3 Cu1 Cu2 O4 -172.04(15) . . . 2_553 ? O3 Cu1 Cu2 O4 7.96(15) 2_553 . . 2_553 ? N1 Cu1 Cu2 O4 -104(100) . . . 2_553 ? O1 Cu1 Cu2 O2 7.30(15) 2_553 . . 2_553 ? O1 Cu1 Cu2 O2 -172.70(15) . . . 2_553 ? O3 Cu1 Cu2 O2 98.28(14) . . . 2_553 ? O3 Cu1 Cu2 O2 -81.72(14) 2_553 . . 2_553 ? N1 Cu1 Cu2 O2 166(100) . . . 2_553 ? O1 Cu1 Cu2 O2 -172.70(15) 2_553 . . . ? O1 Cu1 Cu2 O2 7.30(15) . . . . ? O3 Cu1 Cu2 O2 -81.72(14) . . . . ? O3 Cu1 Cu2 O2 98.28(14) 2_553 . . . ? N1 Cu1 Cu2 O2 -14(100) . . . . ? O1 Cu1 Cu2 N2 21(100) 2_553 . . . ? O1 Cu1 Cu2 N2 -159(100) . . . . ? O3 Cu1 Cu2 N2 112(100) . . . . ? O3 Cu1 Cu2 N2 -68(100) 2_553 . . . ? N1 Cu1 Cu2 N2 0(46) . . . . ? C16 C15 N1 C15 -0.1(3) 1_565 . . 2_553 ? C16 C15 N1 Cu1 179.9(3) 1_565 . . . ? O1 Cu1 N1 C15 29.9(2) 2_553 . . 2_553 ? O1 Cu1 N1 C15 -150.1(2) . . . 2_553 ? O3 Cu1 N1 C15 -61.1(2) . . . 2_553 ? O3 Cu1 N1 C15 118.9(2) 2_553 . . 2_553 ? Cu2 Cu1 N1 C15 -129(100) . . . 2_553 ? O1 Cu1 N1 C15 -150.1(2) 2_553 . . . ? O1 Cu1 N1 C15 29.9(2) . . . . ? O3 Cu1 N1 C15 118.9(2) . . . . ? O3 Cu1 N1 C15 -61.1(2) 2_553 . . . ? Cu2 Cu1 N1 C15 51(100) . . . . ? C15 C16 N2 C16 -0.1(3) 1_545 . . 2_553 ? C15 C16 N2 Cu2 179.9(3) 1_545 . . . ? O4 Cu2 N2 C16 53.1(2) . . . 2_553 ? O4 Cu2 N2 C16 -126.9(2) 2_553 . . 2_553 ? O2 Cu2 N2 C16 -37.2(2) 2_553 . . 2_553 ? O2 Cu2 N2 C16 142.8(2) . . . 2_553 ? Cu1 Cu2 N2 C16 -51(100) . . . 2_553 ? O4 Cu2 N2 C16 -126.9(2) . . . . ? O4 Cu2 N2 C16 53.1(2) 2_553 . . . ? O2 Cu2 N2 C16 142.8(2) 2_553 . . . ? O2 Cu2 N2 C16 -37.2(2) . . . . ? Cu1 Cu2 N2 C16 129(100) . . . . ? O2 C1 O1 Cu1 7.8(6) . . . . ? C2 C1 O1 Cu1 -171.5(3) . . . . ? O1 Cu1 O1 C1 -10.0(3) 2_553 . . . ? O3 Cu1 O1 C1 73.8(3) . . . . ? O3 Cu1 O1 C1 -93.6(3) 2_553 . . . ? N1 Cu1 O1 C1 170.0(3) . . . . ? Cu2 Cu1 O1 C1 -10.0(3) . . . . ? O1 C1 O2 Cu2 2.1(6) . . . . ? C2 C1 O2 Cu2 -178.6(3) . . . . ? O4 Cu2 O2 C1 -93.0(3) . . . . ? O4 Cu2 O2 C1 78.2(3) 2_553 . . . ? O2 Cu2 O2 C1 -7.4(3) 2_553 . . . ? N2 Cu2 O2 C1 172.6(3) . . . . ? Cu1 Cu2 O2 C1 -7.4(3) . . . . ? O4 C8 O3 Cu1 2.0(6) . . . . ? C9 C8 O3 Cu1 -177.2(3) . . . . ? O1 Cu1 O3 C8 77.8(3) 2_553 . . . ? O1 Cu1 O3 C8 -93.8(3) . . . . ? O3 Cu1 O3 C8 -7.9(3) 2_553 . . . ? N1 Cu1 O3 C8 172.1(3) . . . . ? Cu2 Cu1 O3 C8 -7.9(3) . . . . ? O3 C8 O4 Cu2 8.8(6) . . . . ? C9 C8 O4 Cu2 -171.9(3) . . . . ? O4 Cu2 O4 C8 -11.1(3) 2_553 . . . ? O2 Cu2 O4 C8 -94.6(3) 2_553 . . . ? O2 Cu2 O4 C8 72.5(4) . . . . ? N2 Cu2 O4 C8 168.9(3) . . . . ? Cu1 Cu2 O4 C8 -11.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.627 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.088 #===END data_311201 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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 C2/c 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 18.509(2) _cell_length_b 9.6992(11) _cell_length_c 19.275(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.255(3) _cell_angle_gamma 90.00 _cell_volume 3415.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 210 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.296 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5101 _exptl_absorpt_correction_T_max 0.8599 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; sample sealed at 298 K with 19 MPa ; _diffrn_ambient_temperature 210 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12407 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.1110 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4214 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0293P)^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 4214 _refine_ls_number_parameters 222 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.911 _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 C1 C 0.0651(2) 0.7784(4) 0.37591(19) 0.0349(9) Uani 1 1 d . . . C2 C 0.1056(2) 0.7823(4) 0.44942(19) 0.0387(9) Uani 1 1 d . . . C3 C 0.1422(3) 0.6672(4) 0.4789(2) 0.0544(13) Uani 1 1 d . . . H3 H 0.1415 0.5854 0.4526 0.065 Uiso 1 1 calc R . . C4 C 0.1797(3) 0.6719(5) 0.5466(3) 0.0722(15) Uani 1 1 d . . . H4 H 0.2048 0.5933 0.5662 0.087 Uiso 1 1 calc R . . C5 C 0.1806(3) 0.7891(6) 0.5853(2) 0.0752(15) Uani 1 1 d . . . H5 H 0.2057 0.7914 0.6317 0.090 Uiso 1 1 calc R . . C6 C 0.1450(3) 0.9037(5) 0.5564(3) 0.0766(17) Uani 1 1 d . . . H6 H 0.1459 0.9851 0.5829 0.092 Uiso 1 1 calc R . . C7 C 0.1080(3) 0.9007(4) 0.4892(2) 0.0571(13) Uani 1 1 d . . . H7 H 0.0838 0.9804 0.4698 0.068 Uiso 1 1 calc R . . C8 C 0.1237(2) 0.7692(4) 0.21121(17) 0.0324(8) Uani 1 1 d . . . C9 C 0.1990(2) 0.7677(4) 0.19144(18) 0.0344(9) Uani 1 1 d . . . C10 C 0.2285(2) 0.6471(4) 0.1700(2) 0.0492(12) Uani 1 1 d . . . H10 H 0.2020 0.5643 0.1696 0.059 Uiso 1 1 calc R . . C11 C 0.2960(3) 0.6468(5) 0.1492(3) 0.0650(14) Uani 1 1 d . . . H11 H 0.3157 0.5648 0.1341 0.078 Uiso 1 1 calc R . . C12 C 0.3346(2) 0.7682(5) 0.1508(2) 0.0622(13) Uani 1 1 d . . . H12 H 0.3807 0.7690 0.1363 0.075 Uiso 1 1 calc R . . C13 C 0.3067(3) 0.8876(5) 0.1731(2) 0.0580(13) Uani 1 1 d . . . H13 H 0.3339 0.9697 0.1743 0.070 Uiso 1 1 calc R . . C14 C 0.2394(2) 0.8880(4) 0.1939(2) 0.0461(12) Uani 1 1 d . . . H14 H 0.2207 0.9701 0.2098 0.055 Uiso 1 1 calc R . . C15 C 0.03111(19) 0.3442(3) 0.20410(18) 0.0315(9) Uani 1 1 d . . . H15 H 0.0538 0.3918 0.1710 0.038 Uiso 1 1 calc R . . C16 C 0.0311(2) 1.2018(3) 0.20351(18) 0.0328(9) Uani 1 1 d . . . H16 H 0.0533 1.1544 0.1700 0.039 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.64066(5) 0.2500 0.0306(2) Uani 1 2 d S . . Cu2 Cu 0.0000 0.90706(5) 0.2500 0.0324(2) Uani 1 2 d S . . N1 N 0.0000 0.4160(4) 0.2500 0.0268(11) Uani 1 2 d S . . N2 N 0.0000 1.1312(4) 0.2500 0.0283(11) Uani 1 2 d S . . O1 O 0.05599(14) 0.6631(2) 0.34537(13) 0.0389(7) Uani 1 1 d . . . O2 O 0.04203(15) 0.8923(2) 0.34899(13) 0.0422(7) Uani 1 1 d . . . O3 O 0.09162(14) 0.6552(2) 0.21288(13) 0.0385(7) Uani 1 1 d . . . O4 O 0.09833(14) 0.8844(2) 0.22554(14) 0.0394(7) Uani 1 1 d . . . C1S C 0.0723(3) 0.6909(6) 0.0139(3) 0.120(2) Uani 1 1 d D . . H1S H 0.064(3) 0.629(4) 0.0506(17) 0.179 Uiso 1 1 d D . . H3S H 0.1239(6) 0.700(5) 0.014(3) 0.179 Uiso 1 1 d D . . H2S H 0.049(3) 0.655(4) -0.0306(12) 0.179 Uiso 1 1 d D . . H4S H 0.052(3) 0.779(2) 0.022(2) 0.179 Uiso 1 1 d 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 C1 0.032(2) 0.0334(17) 0.041(2) -0.001(2) 0.012(2) -0.001(2) C2 0.040(2) 0.0413(19) 0.034(2) 0.006(2) 0.004(2) -0.004(2) C3 0.070(4) 0.049(2) 0.043(3) 0.005(2) 0.005(3) 0.004(2) C4 0.081(4) 0.070(3) 0.058(4) 0.020(3) -0.011(3) 0.009(3) C5 0.081(4) 0.093(4) 0.046(3) 0.003(3) -0.006(3) -0.014(4) C6 0.104(5) 0.067(3) 0.053(3) -0.010(3) -0.008(3) -0.003(3) C7 0.072(4) 0.047(3) 0.048(3) -0.004(2) -0.003(3) 0.001(2) C8 0.040(2) 0.0269(16) 0.030(2) 0.0016(17) 0.0043(19) 0.0037(19) C9 0.033(2) 0.0346(18) 0.035(2) 0.0027(17) 0.0044(19) -0.0010(19) C10 0.039(3) 0.046(3) 0.065(3) -0.013(2) 0.015(3) -0.005(2) C11 0.047(3) 0.074(3) 0.079(4) -0.020(3) 0.023(3) 0.004(3) C12 0.033(3) 0.099(4) 0.055(3) 0.012(3) 0.007(2) -0.002(3) C13 0.035(3) 0.064(3) 0.072(4) 0.018(3) -0.001(3) -0.011(2) C14 0.041(3) 0.042(2) 0.054(3) 0.0075(19) 0.003(3) -0.004(2) C15 0.039(3) 0.021(2) 0.037(2) 0.0021(15) 0.013(2) -0.0034(16) C16 0.043(3) 0.021(2) 0.038(2) -0.0019(15) 0.018(2) -0.0017(16) Cu1 0.0382(5) 0.0130(3) 0.0414(5) 0.000 0.0091(4) 0.000 Cu2 0.0426(5) 0.0127(3) 0.0416(5) 0.000 0.0058(4) 0.000 N1 0.024(3) 0.019(2) 0.036(3) 0.000 0.002(2) 0.000 N2 0.030(3) 0.018(2) 0.036(3) 0.000 0.004(2) 0.000 O1 0.0513(19) 0.0250(13) 0.0391(18) -0.0026(11) 0.0029(15) 0.0026(12) O2 0.060(2) 0.0247(13) 0.0398(18) -0.0025(11) 0.0024(16) 0.0051(12) O3 0.0409(19) 0.0213(13) 0.0574(18) -0.0032(12) 0.0199(16) -0.0058(11) O4 0.0385(19) 0.0230(13) 0.0594(19) -0.0009(11) 0.0155(16) 0.0011(11) C1S 0.124(6) 0.141(5) 0.102(5) 0.014(4) 0.043(5) 0.037(5) _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 C1 O1 1.263(4) . ? C1 O2 1.265(4) . ? C1 C2 1.493(5) . ? C2 C7 1.377(5) . ? C2 C3 1.379(5) . ? C3 C4 1.377(6) . ? C4 C5 1.359(6) . ? C5 C6 1.365(6) . ? C6 C7 1.365(6) . ? C8 O3 1.259(4) . ? C8 O4 1.260(4) . ? C8 C9 1.503(5) . ? C9 C10 1.382(5) . ? C9 C14 1.382(5) . ? C10 C11 1.373(5) . ? C11 C12 1.374(6) . ? C12 C13 1.365(5) . ? C13 C14 1.368(5) . ? C15 N1 1.328(3) . ? C15 C16 1.381(4) 1_545 ? C16 N2 1.331(3) . ? C16 C15 1.381(4) 1_565 ? Cu1 O3 1.949(2) 2 ? Cu1 O3 1.949(2) . ? Cu1 O1 1.972(2) . ? Cu1 O1 1.972(2) 2 ? Cu1 N1 2.179(3) . ? Cu1 Cu2 2.5839(7) . ? Cu2 O2 1.947(3) . ? Cu2 O2 1.947(3) 2 ? Cu2 O4 1.965(2) . ? Cu2 O4 1.965(2) 2 ? Cu2 N2 2.174(4) . ? N1 C15 1.328(3) 2 ? N2 C16 1.331(3) 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 O1 C1 O2 124.8(3) . . ? O1 C1 C2 118.3(3) . . ? O2 C1 C2 116.9(3) . . ? C7 C2 C3 118.4(4) . . ? C7 C2 C1 121.0(4) . . ? C3 C2 C1 120.6(4) . . ? C4 C3 C2 120.2(4) . . ? C5 C4 C3 120.5(4) . . ? C4 C5 C6 119.6(5) . . ? C5 C6 C7 120.4(5) . . ? C6 C7 C2 120.8(4) . . ? O3 C8 O4 125.4(3) . . ? O3 C8 C9 117.3(3) . . ? O4 C8 C9 117.3(3) . . ? C10 C9 C14 119.1(4) . . ? C10 C9 C8 120.7(3) . . ? C14 C9 C8 120.1(3) . . ? C11 C10 C9 120.7(4) . . ? C10 C11 C12 119.1(4) . . ? C13 C12 C11 120.9(4) . . ? C12 C13 C14 120.1(4) . . ? C13 C14 C9 120.1(4) . . ? N1 C15 C16 122.1(3) . 1_545 ? N2 C16 C15 120.6(3) . 1_565 ? O3 Cu1 O3 171.71(13) 2 . ? O3 Cu1 O1 90.44(11) 2 . ? O3 Cu1 O1 88.65(11) . . ? O3 Cu1 O1 88.65(11) 2 2 ? O3 Cu1 O1 90.44(11) . 2 ? O1 Cu1 O1 167.35(13) . 2 ? O3 Cu1 N1 94.14(6) 2 . ? O3 Cu1 N1 94.14(6) . . ? O1 Cu1 N1 96.33(7) . . ? O1 Cu1 N1 96.33(7) 2 . ? O3 Cu1 Cu2 85.86(6) 2 . ? O3 Cu1 Cu2 85.86(6) . . ? O1 Cu1 Cu2 83.67(7) . . ? O1 Cu1 Cu2 83.67(7) 2 . ? N1 Cu1 Cu2 180.0 . . ? O2 Cu2 O2 171.56(13) . 2 ? O2 Cu2 O4 89.28(11) . . ? O2 Cu2 O4 89.78(11) 2 . ? O2 Cu2 O4 89.78(11) . 2 ? O2 Cu2 O4 89.28(11) 2 2 ? O4 Cu2 O4 167.15(13) . 2 ? O2 Cu2 N2 94.22(7) . . ? O2 Cu2 N2 94.22(7) 2 . ? O4 Cu2 N2 96.43(6) . . ? O4 Cu2 N2 96.43(6) 2 . ? O2 Cu2 Cu1 85.78(7) . . ? O2 Cu2 Cu1 85.78(7) 2 . ? O4 Cu2 Cu1 83.57(6) . . ? O4 Cu2 Cu1 83.57(6) 2 . ? N2 Cu2 Cu1 180.000(1) . . ? C15 N1 C15 116.7(4) 2 . ? C15 N1 Cu1 121.6(2) 2 . ? C15 N1 Cu1 121.6(2) . . ? C16 N2 C16 118.0(4) 2 . ? C16 N2 Cu2 121.0(2) 2 . ? C16 N2 Cu2 121.0(2) . . ? C1 O1 Cu1 122.9(2) . . ? C1 O2 Cu2 121.5(2) . . ? C8 O3 Cu1 121.0(2) . . ? C8 O4 Cu2 123.0(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 O1 C1 C2 C7 -170.2(4) . . . . ? O2 C1 C2 C7 9.3(5) . . . . ? O1 C1 C2 C3 10.4(5) . . . . ? O2 C1 C2 C3 -170.0(3) . . . . ? C7 C2 C3 C4 0.3(7) . . . . ? C1 C2 C3 C4 179.7(4) . . . . ? C2 C3 C4 C5 0.5(7) . . . . ? C3 C4 C5 C6 -0.9(8) . . . . ? C4 C5 C6 C7 0.5(8) . . . . ? C5 C6 C7 C2 0.3(8) . . . . ? C3 C2 C7 C6 -0.7(7) . . . . ? C1 C2 C7 C6 179.9(4) . . . . ? O3 C8 C9 C10 5.6(5) . . . . ? O4 C8 C9 C10 -175.2(3) . . . . ? O3 C8 C9 C14 -175.0(3) . . . . ? O4 C8 C9 C14 4.2(5) . . . . ? C14 C9 C10 C11 -2.0(6) . . . . ? C8 C9 C10 C11 177.4(4) . . . . ? C9 C10 C11 C12 0.8(7) . . . . ? C10 C11 C12 C13 0.5(7) . . . . ? C11 C12 C13 C14 -0.5(7) . . . . ? C12 C13 C14 C9 -0.8(7) . . . . ? C10 C9 C14 C13 2.0(6) . . . . ? C8 C9 C14 C13 -177.4(4) . . . . ? O3 Cu1 Cu2 O2 82.74(11) 2 . . . ? O3 Cu1 Cu2 O2 -97.26(11) . . . . ? O1 Cu1 Cu2 O2 -8.16(12) . . . . ? O1 Cu1 Cu2 O2 171.84(12) 2 . . . ? N1 Cu1 Cu2 O2 -76(39) . . . . ? O3 Cu1 Cu2 O2 -97.26(11) 2 . . 2 ? O3 Cu1 Cu2 O2 82.74(11) . . . 2 ? O1 Cu1 Cu2 O2 171.84(12) . . . 2 ? O1 Cu1 Cu2 O2 -8.16(12) 2 . . 2 ? N1 Cu1 Cu2 O2 104(37) . . . 2 ? O3 Cu1 Cu2 O4 172.49(12) 2 . . . ? O3 Cu1 Cu2 O4 -7.51(12) . . . . ? O1 Cu1 Cu2 O4 81.58(11) . . . . ? O1 Cu1 Cu2 O4 -98.42(11) 2 . . . ? N1 Cu1 Cu2 O4 14(37) . . . . ? O3 Cu1 Cu2 O4 -7.51(12) 2 . . 2 ? O3 Cu1 Cu2 O4 172.49(12) . . . 2 ? O1 Cu1 Cu2 O4 -98.42(11) . . . 2 ? O1 Cu1 Cu2 O4 81.58(11) 2 . . 2 ? N1 Cu1 Cu2 O4 -166(39) . . . 2 ? O3 Cu1 Cu2 N2 -21(100) 2 . . . ? O3 Cu1 Cu2 N2 159(100) . . . . ? O1 Cu1 Cu2 N2 -112(100) . . . . ? O1 Cu1 Cu2 N2 68(100) 2 . . . ? N1 Cu1 Cu2 N2 0(38) . . . . ? C16 C15 N1 C15 0.3(3) 1_545 . . 2 ? C16 C15 N1 Cu1 -179.7(3) 1_545 . . . ? O3 Cu1 N1 C15 -29.26(19) 2 . . 2 ? O3 Cu1 N1 C15 150.74(19) . . . 2 ? O1 Cu1 N1 C15 61.6(2) . . . 2 ? O1 Cu1 N1 C15 -118.4(2) 2 . . 2 ? Cu2 Cu1 N1 C15 129(39) . . . 2 ? O3 Cu1 N1 C15 150.74(19) 2 . . . ? O3 Cu1 N1 C15 -29.26(19) . . . . ? O1 Cu1 N1 C15 -118.4(2) . . . . ? O1 Cu1 N1 C15 61.6(2) 2 . . . ? Cu2 Cu1 N1 C15 -51(38) . . . . ? C15 C16 N2 C16 0.3(3) 1_565 . . 2 ? C15 C16 N2 Cu2 -179.7(3) 1_565 . . . ? O2 Cu2 N2 C16 -53.2(2) . . . 2 ? O2 Cu2 N2 C16 126.8(2) 2 . . 2 ? O4 Cu2 N2 C16 -142.95(19) . . . 2 ? O4 Cu2 N2 C16 37.05(19) 2 . . 2 ? Cu1 Cu2 N2 C16 51(100) . . . 2 ? O2 Cu2 N2 C16 126.8(2) . . . . ? O2 Cu2 N2 C16 -53.2(2) 2 . . . ? O4 Cu2 N2 C16 37.05(19) . . . . ? O4 Cu2 N2 C16 -142.95(19) 2 . . . ? Cu1 Cu2 N2 C16 -129(100) . . . . ? O2 C1 O1 Cu1 -2.3(5) . . . . ? C2 C1 O1 Cu1 177.2(2) . . . . ? O3 Cu1 O1 C1 -77.6(3) 2 . . . ? O3 Cu1 O1 C1 94.1(3) . . . . ? O1 Cu1 O1 C1 8.2(3) 2 . . . ? N1 Cu1 O1 C1 -171.8(3) . . . . ? Cu2 Cu1 O1 C1 8.2(3) . . . . ? O1 C1 O2 Cu2 -8.8(5) . . . . ? C2 C1 O2 Cu2 171.7(2) . . . . ? O2 Cu2 O2 C1 11.2(3) 2 . . . ? O4 Cu2 O2 C1 -72.4(3) . . . . ? O4 Cu2 O2 C1 94.8(3) 2 . . . ? N2 Cu2 O2 C1 -168.8(3) . . . . ? Cu1 Cu2 O2 C1 11.2(3) . . . . ? O4 C8 O3 Cu1 -7.6(5) . . . . ? C9 C8 O3 Cu1 171.5(2) . . . . ? O3 Cu1 O3 C8 10.1(3) 2 . . . ? O1 Cu1 O3 C8 -73.7(3) . . . . ? O1 Cu1 O3 C8 93.7(3) 2 . . . ? N1 Cu1 O3 C8 -169.9(3) . . . . ? Cu2 Cu1 O3 C8 10.1(3) . . . . ? O3 C8 O4 Cu2 -2.5(5) . . . . ? C9 C8 O4 Cu2 178.3(2) . . . . ? O2 Cu2 O4 C8 93.6(3) . . . . ? O2 Cu2 O4 C8 -78.0(3) 2 . . . ? O4 Cu2 O4 C8 7.7(3) 2 . . . ? N2 Cu2 O4 C8 -172.3(3) . . . . ? Cu1 Cu2 O4 C8 7.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.640 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.081 #===END data_311181 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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' _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 9.696(2) _cell_length_b 10.228(2) _cell_length_c 10.701(3) _cell_angle_alpha 71.406(4) _cell_angle_beta 64.570(4) _cell_angle_gamma 62.944(5) _cell_volume 843.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 1.313 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5064 _exptl_absorpt_correction_T_max 0.8584 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; sample sealed at 298 K with 19 MPa ; _diffrn_ambient_temperature 150 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6268 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.1606 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4140 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.1151P)^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 4140 _refine_ls_number_parameters 220 _refine_ls_number_restraints 277 _refine_ls_R_factor_all 0.1521 _refine_ls_R_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.2394 _refine_ls_wR_factor_gt 0.2124 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.942 _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 C1 C 0.5441(8) 0.6284(8) 0.2491(8) 0.0312(15) Uani 1 1 d U . . C2 C 0.5635(8) 0.7095(9) 0.1026(7) 0.0335(16) Uani 1 1 d U . . C3 C 0.4748(10) 0.7115(10) 0.0293(9) 0.048(2) Uani 1 1 d U . . H3 H 0.3996 0.6617 0.0729 0.057 Uiso 1 1 calc R . . C4 C 0.4938(11) 0.7839(12) -0.1049(9) 0.059(3) Uani 1 1 d U . . H4 H 0.4337 0.7823 -0.1546 0.071 Uiso 1 1 calc R . . C5 C 0.6016(11) 0.8605(11) -0.1698(10) 0.057(2) Uani 1 1 d U . . H5 H 0.6124 0.9140 -0.2620 0.068 Uiso 1 1 calc R . . C6 C 0.6902(11) 0.8568(11) -0.0981(10) 0.057(2) Uani 1 1 d U . . H6 H 0.7659 0.9061 -0.1416 0.068 Uiso 1 1 calc R . . C7 C 0.6720(9) 0.7836(10) 0.0348(8) 0.044(2) Uani 1 1 d U . . H7 H 0.7353 0.7829 0.0827 0.052 Uiso 1 1 calc R . . C8 C 0.3338(7) 0.7525(8) 0.5765(7) 0.0293(15) Uani 1 1 d U . . C9 C 0.2283(8) 0.9044(8) 0.6188(7) 0.0303(15) Uani 1 1 d U . . C10 C 0.0595(8) 0.9624(9) 0.6450(8) 0.0375(18) Uani 1 1 d U . . H10 H 0.0105 0.9066 0.6339 0.045 Uiso 1 1 calc R . . C11 C -0.0373(9) 1.1001(9) 0.6868(9) 0.045(2) Uani 1 1 d U . . H11 H -0.1521 1.1401 0.7028 0.055 Uiso 1 1 calc R . . C12 C 0.0335(11) 1.1784(10) 0.7050(9) 0.051(2) Uani 1 1 d U . . H12 H -0.0335 1.2719 0.7363 0.061 Uiso 1 1 calc R . . C13 C 0.2015(11) 1.1237(9) 0.6784(8) 0.044(2) Uani 1 1 d U . . H13 H 0.2493 1.1798 0.6908 0.053 Uiso 1 1 calc R . . C14 C 0.2982(9) 0.9880(8) 0.6343(7) 0.0329(16) Uani 1 1 d U . . H14 H 0.4137 0.9509 0.6142 0.039 Uiso 1 1 calc R . . C15 C 0.1461(7) 0.4287(8) 0.4130(7) 0.0243(14) Uani 1 1 d U . . H15 H 0.2487 0.3746 0.3510 0.029 Uiso 1 1 calc R . . C16 C -0.0021(7) 0.5610(8) 0.5934(7) 0.0257(14) Uani 1 1 d U . . H16 H -0.0083 0.6038 0.6634 0.031 Uiso 1 1 calc R . . Cu1 Cu 0.37060(9) 0.48842(10) 0.50442(9) 0.0249(3) Uani 1 1 d U . . N1 N 0.1436(6) 0.4939(5) 0.5058(5) 0.0191(11) Uani 1 1 d U . . O1 O 0.4267(5) 0.5830(6) 0.3088(5) 0.0357(12) Uani 1 1 d U . . O2 O 0.6469(6) 0.6094(6) 0.3017(5) 0.0335(11) Uani 1 1 d U . . O3 O 0.2602(6) 0.6853(6) 0.5652(5) 0.0347(12) Uani 1 1 d U . . O4 O 0.4840(5) 0.7055(6) 0.5566(5) 0.0322(11) Uani 1 1 d U . . C1S C 0.8744(13) 0.3479(13) 0.0343(11) 0.087(4) Uani 1 1 d DU . . H1S H 0.923(9) 0.397(8) -0.056(4) 0.130 Uiso 1 1 d D . . H2S H 0.933(9) 0.2425(18) 0.038(9) 0.130 Uiso 1 1 d D . . H3S H 0.761(3) 0.372(9) 0.048(9) 0.130 Uiso 1 1 d D . . H4S H 0.881(10) 0.380(9) 0.106(6) 0.130 Uiso 1 1 d 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 C1 0.024(3) 0.027(4) 0.042(4) -0.009(3) -0.012(3) -0.006(3) C2 0.029(3) 0.035(4) 0.033(4) -0.002(3) -0.011(3) -0.011(3) C3 0.046(4) 0.053(5) 0.047(5) 0.012(4) -0.027(4) -0.023(4) C4 0.070(6) 0.085(7) 0.033(4) 0.021(5) -0.034(4) -0.042(6) C5 0.068(6) 0.055(6) 0.044(5) 0.014(5) -0.026(4) -0.028(5) C6 0.058(5) 0.061(6) 0.050(5) 0.007(5) -0.014(4) -0.034(5) C7 0.046(4) 0.056(6) 0.036(4) 0.001(4) -0.017(4) -0.027(4) C8 0.024(3) 0.044(4) 0.023(3) 0.003(3) -0.014(3) -0.015(3) C9 0.033(3) 0.035(4) 0.023(3) 0.001(3) -0.011(3) -0.015(3) C10 0.030(4) 0.032(4) 0.048(5) -0.004(4) -0.014(3) -0.011(3) C11 0.035(4) 0.038(5) 0.050(5) -0.011(4) -0.008(4) -0.005(4) C12 0.060(5) 0.034(5) 0.046(5) 0.002(4) -0.022(4) -0.009(4) C13 0.069(5) 0.027(4) 0.047(5) 0.001(4) -0.032(4) -0.018(4) C14 0.039(4) 0.034(4) 0.030(4) 0.005(3) -0.019(3) -0.017(3) C15 0.020(3) 0.026(4) 0.025(3) -0.006(3) -0.004(2) -0.008(3) C16 0.029(3) 0.026(4) 0.025(3) -0.005(3) -0.008(3) -0.012(3) Cu1 0.0193(4) 0.0290(5) 0.0297(5) -0.0033(3) -0.0122(3) -0.0089(3) N1 0.021(2) 0.007(3) 0.020(3) 0.003(2) -0.012(2) 0.003(2) O1 0.030(2) 0.052(3) 0.030(3) -0.004(3) -0.011(2) -0.019(2) O2 0.033(2) 0.041(3) 0.031(3) 0.001(2) -0.015(2) -0.017(2) O3 0.031(2) 0.030(3) 0.046(3) -0.011(3) -0.017(2) -0.006(2) O4 0.025(2) 0.032(3) 0.043(3) -0.011(2) -0.013(2) -0.008(2) C1S 0.094(9) 0.083(9) 0.073(8) -0.017(7) -0.032(7) -0.018(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 C1 O2 1.258(8) . ? C1 O1 1.260(7) . ? C1 C2 1.497(10) . ? C2 C3 1.382(10) . ? C2 C7 1.388(10) . ? C3 C4 1.365(11) . ? C4 C5 1.401(12) . ? C5 C6 1.359(12) . ? C6 C7 1.356(11) . ? C8 O4 1.249(7) . ? C8 O3 1.252(7) . ? C8 C9 1.507(10) . ? C9 C14 1.390(9) . ? C9 C10 1.392(9) . ? C10 C11 1.380(10) . ? C11 C12 1.365(11) . ? C12 C13 1.387(11) . ? C13 C14 1.372(10) . ? C15 N1 1.348(8) . ? C15 C16 1.382(8) 2_566 ? C16 N1 1.318(7) . ? C16 C15 1.382(8) 2_566 ? Cu1 O1 1.955(5) . ? Cu1 O4 1.959(5) 2_666 ? Cu1 O2 1.966(5) 2_666 ? Cu1 O3 1.975(5) . ? Cu1 N1 2.170(5) . ? Cu1 Cu1 2.5855(15) 2_666 ? O2 Cu1 1.966(5) 2_666 ? O4 Cu1 1.959(5) 2_666 ? 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 C1 O1 125.5(7) . . ? O2 C1 C2 117.7(6) . . ? O1 C1 C2 116.8(6) . . ? C3 C2 C7 117.6(7) . . ? C3 C2 C1 120.9(6) . . ? C7 C2 C1 121.5(6) . . ? C4 C3 C2 120.9(7) . . ? C3 C4 C5 120.3(8) . . ? C6 C5 C4 118.6(8) . . ? C7 C6 C5 120.8(8) . . ? C6 C7 C2 121.7(7) . . ? O4 C8 O3 126.3(7) . . ? O4 C8 C9 117.8(6) . . ? O3 C8 C9 115.8(6) . . ? C14 C9 C10 118.9(7) . . ? C14 C9 C8 120.3(6) . . ? C10 C9 C8 120.8(6) . . ? C11 C10 C9 120.6(7) . . ? C12 C11 C10 119.3(7) . . ? C11 C12 C13 121.2(8) . . ? C14 C13 C12 119.4(7) . . ? C13 C14 C9 120.4(7) . . ? N1 C15 C16 121.2(5) . 2_566 ? N1 C16 C15 122.3(6) . 2_566 ? O1 Cu1 O4 89.3(2) . 2_666 ? O1 Cu1 O2 169.68(17) . 2_666 ? O4 Cu1 O2 88.5(2) 2_666 2_666 ? O1 Cu1 O3 90.0(2) . . ? O4 Cu1 O3 169.68(17) 2_666 . ? O2 Cu1 O3 90.4(2) 2_666 . ? O1 Cu1 N1 92.42(18) . . ? O4 Cu1 N1 98.08(18) 2_666 . ? O2 Cu1 N1 97.87(18) 2_666 . ? O3 Cu1 N1 92.23(19) . . ? O1 Cu1 Cu1 84.44(13) . 2_666 ? O4 Cu1 Cu1 86.96(13) 2_666 2_666 ? O2 Cu1 Cu1 85.38(13) 2_666 2_666 ? O3 Cu1 Cu1 82.73(13) . 2_666 ? N1 Cu1 Cu1 174.05(14) . 2_666 ? C16 N1 C15 116.4(5) . . ? C16 N1 Cu1 123.1(4) . . ? C15 N1 Cu1 120.4(4) . . ? C1 O1 Cu1 123.0(5) . . ? C1 O2 Cu1 121.5(4) . 2_666 ? C8 O3 Cu1 124.0(5) . . ? C8 O4 Cu1 120.0(4) . 2_666 ? 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 O2 C1 C2 C3 168.3(7) . . . . ? O1 C1 C2 C3 -10.8(11) . . . . ? O2 C1 C2 C7 -10.8(11) . . . . ? O1 C1 C2 C7 170.1(7) . . . . ? C7 C2 C3 C4 0.0(13) . . . . ? C1 C2 C3 C4 -179.2(8) . . . . ? C2 C3 C4 C5 -1.4(15) . . . . ? C3 C4 C5 C6 2.2(16) . . . . ? C4 C5 C6 C7 -1.6(16) . . . . ? C5 C6 C7 C2 0.2(15) . . . . ? C3 C2 C7 C6 0.7(13) . . . . ? C1 C2 C7 C6 179.8(8) . . . . ? O4 C8 C9 C14 0.1(10) . . . . ? O3 C8 C9 C14 179.9(6) . . . . ? O4 C8 C9 C10 -178.9(6) . . . . ? O3 C8 C9 C10 1.0(10) . . . . ? C14 C9 C10 C11 -0.5(11) . . . . ? C8 C9 C10 C11 178.5(7) . . . . ? C9 C10 C11 C12 -1.2(12) . . . . ? C10 C11 C12 C13 1.8(13) . . . . ? C11 C12 C13 C14 -0.5(12) . . . . ? C12 C13 C14 C9 -1.3(11) . . . . ? C10 C9 C14 C13 1.8(10) . . . . ? C8 C9 C14 C13 -177.2(7) . . . . ? C15 C16 N1 C15 -3.2(10) 2_566 . . . ? C15 C16 N1 Cu1 175.8(5) 2_566 . . . ? C16 C15 N1 C16 3.2(10) 2_566 . . . ? C16 C15 N1 Cu1 -175.9(5) 2_566 . . . ? O1 Cu1 N1 C16 -121.9(5) . . . . ? O4 Cu1 N1 C16 148.5(5) 2_666 . . . ? O2 Cu1 N1 C16 58.9(5) 2_666 . . . ? O3 Cu1 N1 C16 -31.8(5) . . . . ? Cu1 Cu1 N1 C16 -63.9(16) 2_666 . . . ? O1 Cu1 N1 C15 57.1(5) . . . . ? O4 Cu1 N1 C15 -32.5(5) 2_666 . . . ? O2 Cu1 N1 C15 -122.1(5) 2_666 . . . ? O3 Cu1 N1 C15 147.2(5) . . . . ? Cu1 Cu1 N1 C15 115.1(14) 2_666 . . . ? O2 C1 O1 Cu1 5.9(10) . . . . ? C2 C1 O1 Cu1 -175.2(5) . . . . ? O4 Cu1 O1 C1 -91.2(6) 2_666 . . . ? O2 Cu1 O1 C1 -13.6(16) 2_666 . . . ? O3 Cu1 O1 C1 78.5(6) . . . . ? N1 Cu1 O1 C1 170.8(6) . . . . ? Cu1 Cu1 O1 C1 -4.2(5) 2_666 . . . ? O1 C1 O2 Cu1 -3.5(10) . . . 2_666 ? C2 C1 O2 Cu1 177.6(5) . . . 2_666 ? O4 C8 O3 Cu1 -2.6(10) . . . . ? C9 C8 O3 Cu1 177.5(4) . . . . ? O1 Cu1 O3 C8 -83.0(5) . . . . ? O4 Cu1 O3 C8 3.0(15) 2_666 . . . ? O2 Cu1 O3 C8 86.7(5) 2_666 . . . ? N1 Cu1 O3 C8 -175.4(5) . . . . ? Cu1 Cu1 O3 C8 1.4(5) 2_666 . . . ? O3 C8 O4 Cu1 2.2(9) . . . 2_666 ? C9 C8 O4 Cu1 -178.0(4) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 4.279 _refine_diff_density_min -0.991 _refine_diff_density_rms 0.211 #===END data_311191 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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' _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 9.693(2) _cell_length_b 10.195(2) _cell_length_c 10.692(2) _cell_angle_alpha 71.428(5) _cell_angle_beta 64.517(5) _cell_angle_gamma 62.919(5) _cell_volume 839.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5050 _exptl_absorpt_correction_T_max 0.8578 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; sample sealed at 298 K with 19 MPa ; _diffrn_ambient_temperature 120 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6260 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.1457 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4135 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.1166P)^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 4135 _refine_ls_number_parameters 220 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1427 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2247 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.957 _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 C1 C 0.6678(7) 0.2464(8) 0.4237(7) 0.0258(14) Uani 1 1 d . . . C2 C 0.7727(8) 0.0936(8) 0.3811(7) 0.0258(14) Uani 1 1 d . . . C3 C 0.7027(9) 0.0103(8) 0.3651(7) 0.0290(15) Uani 1 1 d . . . H3 H 0.5872 0.0476 0.3846 0.035 Uiso 1 1 calc R . . C4 C 0.8009(10) -0.1266(8) 0.3208(8) 0.0388(18) Uani 1 1 d . . . H4 H 0.7535 -0.1839 0.3096 0.047 Uiso 1 1 calc R . . C5 C 0.9677(10) -0.1795(9) 0.2931(8) 0.0422(19) Uani 1 1 d . . . H5 H 1.0355 -0.2725 0.2601 0.051 Uiso 1 1 calc R . . C6 C 1.0380(9) -0.1008(9) 0.3122(8) 0.0400(19) Uani 1 1 d . . . H6 H 1.1529 -0.1408 0.2958 0.048 Uiso 1 1 calc R . . C7 C 0.9415(8) 0.0363(8) 0.3551(8) 0.0320(16) Uani 1 1 d . . . H7 H 0.9901 0.0920 0.3670 0.038 Uiso 1 1 calc R . . C8 C 0.4559(7) 0.3729(7) 0.7513(7) 0.0264(15) Uani 1 1 d . . . C9 C 0.4346(8) 0.2929(8) 0.8979(7) 0.0285(15) Uani 1 1 d . . . C10 C 0.3271(9) 0.2171(9) 0.9641(8) 0.0371(18) Uani 1 1 d . . . H10 H 0.2644 0.2177 0.9158 0.045 Uiso 1 1 calc R . . C11 C 0.3101(10) 0.1415(10) 1.0981(10) 0.051(2) Uani 1 1 d . . . H11 H 0.2360 0.0904 1.1415 0.061 Uiso 1 1 calc R . . C12 C 0.3998(10) 0.1395(10) 1.1697(9) 0.048(2) Uani 1 1 d . . . H12 H 0.3888 0.0869 1.2623 0.058 Uiso 1 1 calc R . . C13 C 0.5062(11) 0.2152(11) 1.1049(8) 0.049(2) Uani 1 1 d . . . H13 H 0.5683 0.2147 1.1538 0.059 Uiso 1 1 calc R . . C14 C 0.5235(9) 0.2905(10) 0.9718(8) 0.043(2) Uani 1 1 d . . . H14 H 0.5972 0.3420 0.9293 0.051 Uiso 1 1 calc R . . C15 C -0.0034(7) 0.5615(7) 0.5937(7) 0.0222(13) Uani 1 1 d . . . H15 H -0.0103 0.6049 0.6638 0.027 Uiso 1 1 calc R . . C16 C 0.1455(7) 0.4289(7) 0.4135(6) 0.0205(13) Uani 1 1 d . . . H16 H 0.2482 0.3746 0.3512 0.025 Uiso 1 1 calc R . . Cu1 Cu 0.37048(9) 0.48830(10) 0.50446(9) 0.0211(3) Uani 1 1 d . . . N1 N 0.1447(6) 0.4930(5) 0.5049(5) 0.0166(10) Uani 1 1 d . . . O1 O 0.5164(5) 0.2935(5) 0.4436(5) 0.0301(11) Uani 1 1 d . . . O2 O 0.7395(5) 0.3150(5) 0.4355(5) 0.0298(11) Uani 1 1 d . . . O3 O 0.3522(5) 0.3915(5) 0.6985(5) 0.0287(11) Uani 1 1 d . . . O4 O 0.5732(5) 0.4166(6) 0.6920(5) 0.0310(11) Uani 1 1 d . . . C1S C 0.1231(12) 0.6545(12) 0.9649(11) 0.080(3) Uani 1 1 d D . . H1S H 0.085(10) 0.7599(19) 0.962(9) 0.119 Uiso 1 1 d D . . H2S H 0.050(8) 0.615(9) 1.046(5) 0.119 Uiso 1 1 d D . . H3S H 0.232(4) 0.607(8) 0.970(9) 0.119 Uiso 1 1 d D . . H4S H 0.125(10) 0.635(9) 0.882(5) 0.119 Uiso 1 1 d 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 C1 0.027(3) 0.037(4) 0.019(3) 0.003(3) -0.007(2) -0.021(3) C2 0.033(3) 0.027(4) 0.021(3) 0.003(3) -0.010(3) -0.017(3) C3 0.034(3) 0.026(4) 0.029(4) 0.003(3) -0.013(3) -0.015(3) C4 0.064(5) 0.020(4) 0.043(5) 0.000(4) -0.027(4) -0.018(4) C5 0.061(5) 0.024(4) 0.039(5) -0.001(4) -0.019(4) -0.014(4) C6 0.030(4) 0.036(4) 0.041(5) -0.003(4) -0.006(3) -0.010(3) C7 0.027(3) 0.028(4) 0.039(4) 0.001(3) -0.011(3) -0.014(3) C8 0.021(3) 0.023(3) 0.040(4) -0.017(3) -0.009(3) -0.005(3) C9 0.026(3) 0.026(4) 0.032(4) -0.007(3) -0.010(3) -0.006(3) C10 0.043(4) 0.042(5) 0.033(4) -0.001(4) -0.013(3) -0.024(4) C11 0.053(5) 0.054(6) 0.054(6) 0.005(5) -0.015(4) -0.038(5) C12 0.057(5) 0.042(5) 0.039(5) 0.004(4) -0.015(4) -0.022(4) C13 0.064(5) 0.065(6) 0.029(4) 0.014(4) -0.028(4) -0.034(5) C14 0.043(4) 0.055(5) 0.040(5) 0.007(4) -0.020(3) -0.030(4) C15 0.026(3) 0.025(3) 0.018(3) -0.004(3) -0.006(2) -0.013(3) C16 0.021(3) 0.020(3) 0.020(3) -0.005(3) -0.003(2) -0.010(3) Cu1 0.0187(4) 0.0256(4) 0.0256(4) -0.0030(3) -0.0097(3) -0.0123(3) N1 0.023(2) 0.011(3) 0.016(3) 0.000(2) -0.0115(19) -0.003(2) O1 0.024(2) 0.030(3) 0.042(3) -0.007(2) -0.013(2) -0.012(2) O2 0.025(2) 0.024(3) 0.046(3) -0.012(2) -0.012(2) -0.009(2) O3 0.027(2) 0.035(3) 0.031(3) -0.001(2) -0.0114(19) -0.018(2) O4 0.029(2) 0.048(3) 0.025(3) 0.000(2) -0.0118(19) -0.023(2) C1S 0.079(7) 0.086(9) 0.076(8) -0.014(7) -0.036(6) -0.021(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 C1 O2 1.250(7) . ? C1 O1 1.259(7) . ? C1 C2 1.510(9) . ? C2 C3 1.388(9) . ? C2 C7 1.392(9) . ? C3 C4 1.379(10) . ? C4 C5 1.375(11) . ? C5 C6 1.367(10) . ? C6 C7 1.374(10) . ? C8 O4 1.247(7) . ? C8 O3 1.269(7) . ? C8 C9 1.492(10) . ? C9 C14 1.386(9) . ? C9 C10 1.390(9) . ? C10 C11 1.372(11) . ? C11 C12 1.375(11) . ? C12 C13 1.381(11) . ? C13 C14 1.363(11) . ? C15 N1 1.336(7) . ? C15 C16 1.370(8) 2_566 ? C16 N1 1.334(7) . ? C16 C15 1.370(8) 2_566 ? Cu1 O1 1.960(5) . ? Cu1 O4 1.962(5) 2_666 ? Cu1 O3 1.962(5) . ? Cu1 O2 1.963(5) 2_666 ? Cu1 N1 2.165(5) . ? Cu1 Cu1 2.5875(14) 2_666 ? O2 Cu1 1.963(5) 2_666 ? O4 Cu1 1.962(5) 2_666 ? 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 C1 O1 125.9(7) . . ? O2 C1 C2 116.9(5) . . ? O1 C1 C2 117.2(5) . . ? C3 C2 C7 119.5(6) . . ? C3 C2 C1 120.5(6) . . ? C7 C2 C1 120.0(6) . . ? C4 C3 C2 119.9(7) . . ? C5 C4 C3 119.5(7) . . ? C6 C5 C4 121.3(7) . . ? C5 C6 C7 119.7(7) . . ? C6 C7 C2 120.1(6) . . ? O4 C8 O3 125.9(7) . . ? O4 C8 C9 117.0(6) . . ? O3 C8 C9 117.1(6) . . ? C14 C9 C10 117.9(7) . . ? C14 C9 C8 120.8(6) . . ? C10 C9 C8 121.3(6) . . ? C11 C10 C9 121.2(7) . . ? C10 C11 C12 120.2(7) . . ? C11 C12 C13 119.0(8) . . ? C14 C13 C12 121.0(7) . . ? C13 C14 C9 120.7(7) . . ? N1 C15 C16 122.0(6) . 2_566 ? N1 C16 C15 122.3(5) . 2_566 ? O1 Cu1 O4 89.4(2) . 2_666 ? O1 Cu1 O3 88.7(2) . . ? O4 Cu1 O3 169.73(16) 2_666 . ? O1 Cu1 O2 169.65(17) . 2_666 ? O4 Cu1 O2 89.8(2) 2_666 2_666 ? O3 Cu1 O2 90.3(2) . 2_666 ? O1 Cu1 N1 97.89(18) . . ? O4 Cu1 N1 92.22(18) 2_666 . ? O3 Cu1 N1 98.04(18) . . ? O2 Cu1 N1 92.45(18) 2_666 . ? O1 Cu1 Cu1 86.91(13) . 2_666 ? O4 Cu1 Cu1 84.46(12) 2_666 2_666 ? O3 Cu1 Cu1 85.36(12) . 2_666 ? O2 Cu1 Cu1 82.75(13) 2_666 2_666 ? N1 Cu1 Cu1 174.15(14) . 2_666 ? C16 N1 C15 115.7(5) . . ? C16 N1 Cu1 121.4(4) . . ? C15 N1 Cu1 122.9(4) . . ? C1 O1 Cu1 119.8(4) . . ? C1 O2 Cu1 124.6(4) . 2_666 ? C8 O3 Cu1 121.3(4) . . ? C8 O4 Cu1 122.8(4) . 2_666 ? 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 O2 C1 C2 C3 -179.8(6) . . . . ? O1 C1 C2 C3 0.0(10) . . . . ? O2 C1 C2 C7 -0.9(10) . . . . ? O1 C1 C2 C7 178.9(6) . . . . ? C7 C2 C3 C4 -1.4(10) . . . . ? C1 C2 C3 C4 177.5(6) . . . . ? C2 C3 C4 C5 0.1(11) . . . . ? C3 C4 C5 C6 1.8(12) . . . . ? C4 C5 C6 C7 -2.3(12) . . . . ? C5 C6 C7 C2 1.0(12) . . . . ? C3 C2 C7 C6 0.9(11) . . . . ? C1 C2 C7 C6 -178.0(7) . . . . ? O4 C8 C9 C14 10.8(10) . . . . ? O3 C8 C9 C14 -168.6(7) . . . . ? O4 C8 C9 C10 -168.5(6) . . . . ? O3 C8 C9 C10 12.2(10) . . . . ? C14 C9 C10 C11 -0.4(12) . . . . ? C8 C9 C10 C11 178.8(7) . . . . ? C9 C10 C11 C12 0.0(13) . . . . ? C10 C11 C12 C13 0.3(14) . . . . ? C11 C12 C13 C14 -0.3(14) . . . . ? C12 C13 C14 C9 -0.1(14) . . . . ? C10 C9 C14 C13 0.4(12) . . . . ? C8 C9 C14 C13 -178.8(7) . . . . ? C15 C16 N1 C15 3.0(10) 2_566 . . . ? C15 C16 N1 Cu1 -175.9(5) 2_566 . . . ? C16 C15 N1 C16 -3.0(10) 2_566 . . . ? C16 C15 N1 Cu1 175.9(5) 2_566 . . . ? O1 Cu1 N1 C16 -32.7(5) . . . . ? O4 Cu1 N1 C16 57.0(5) 2_666 . . . ? O3 Cu1 N1 C16 -122.5(5) . . . . ? O2 Cu1 N1 C16 146.9(5) 2_666 . . . ? Cu1 Cu1 N1 C16 112.3(14) 2_666 . . . ? O1 Cu1 N1 C15 148.5(5) . . . . ? O4 Cu1 N1 C15 -121.8(5) 2_666 . . . ? O3 Cu1 N1 C15 58.7(5) . . . . ? O2 Cu1 N1 C15 -31.9(5) 2_666 . . . ? Cu1 Cu1 N1 C15 -66.5(16) 2_666 . . . ? O2 C1 O1 Cu1 -2.0(9) . . . . ? C2 C1 O1 Cu1 178.2(4) . . . . ? O4 Cu1 O1 C1 85.2(5) 2_666 . . . ? O3 Cu1 O1 C1 -84.7(5) . . . . ? O2 Cu1 O1 C1 -0.4(15) 2_666 . . . ? N1 Cu1 O1 C1 177.4(5) . . . . ? Cu1 Cu1 O1 C1 0.7(5) 2_666 . . . ? O1 C1 O2 Cu1 2.4(10) . . . 2_666 ? C2 C1 O2 Cu1 -177.9(4) . . . 2_666 ? O4 C8 O3 Cu1 3.0(9) . . . . ? C9 C8 O3 Cu1 -177.7(4) . . . . ? O1 Cu1 O3 C8 86.9(5) . . . . ? O4 Cu1 O3 C8 7.5(15) 2_666 . . . ? O2 Cu1 O3 C8 -82.8(5) 2_666 . . . ? N1 Cu1 O3 C8 -175.4(5) . . . . ? Cu1 Cu1 O3 C8 -0.1(5) 2_666 . . . ? O3 C8 O4 Cu1 -4.9(9) . . . 2_666 ? C9 C8 O4 Cu1 175.8(4) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 3.067 _refine_diff_density_min -1.101 _refine_diff_density_rms 0.258 #===END data_311231 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cu2 N2 O8' _chemical_formula_weight 723.72 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' _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 9.678(3) _cell_length_b 10.148(3) _cell_length_c 10.688(4) _cell_angle_alpha 71.471(7) _cell_angle_beta 64.337(6) _cell_angle_gamma 62.787(7) _cell_volume 832.0(5) _cell_formula_units_Z 1 _cell_measurement_temperature 90 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 1.331 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5024 _exptl_absorpt_correction_T_max 0.8566 _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 90 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5885 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.2143 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4052 _reflns_number_gt 1787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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 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^)+(0.0541P)^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 4052 _refine_ls_number_parameters 220 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.1753 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.950 _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 C1 C 0.3337(8) 0.7555(8) 0.5749(7) 0.0211(14) Uani 1 1 d . . . C2 C 0.2267(8) 0.9090(8) 0.6191(6) 0.0199(14) Uani 1 1 d . . . C3 C 0.0569(8) 0.9678(8) 0.6445(7) 0.0251(16) Uani 1 1 d . . . H3 H 0.0095 0.9124 0.6302 0.030 Uiso 1 1 calc R . . C4 C -0.0420(8) 1.1037(9) 0.6896(8) 0.0343(19) Uani 1 1 d . . . H4 H -0.1575 1.1434 0.7068 0.041 Uiso 1 1 calc R . . C5 C 0.0309(9) 1.1821(9) 0.7094(8) 0.0358(18) Uani 1 1 d . . . H5 H -0.0367 1.2760 0.7422 0.043 Uiso 1 1 calc R . . C6 C 0.1968(10) 1.1284(8) 0.6832(7) 0.0309(18) Uani 1 1 d . . . H6 H 0.2439 1.1845 0.6969 0.037 Uiso 1 1 calc R . . C7 C 0.2970(8) 0.9893(8) 0.6359(7) 0.0254(16) Uani 1 1 d . . . H7 H 0.4130 0.9511 0.6157 0.030 Uiso 1 1 calc R . . C8 C 0.5448(7) 0.6253(8) 0.2503(7) 0.0216(15) Uani 1 1 d . . . C9 C 0.5657(8) 0.7095(8) 0.0995(7) 0.0245(15) Uani 1 1 d . . . C10 C 0.4759(9) 0.7097(9) 0.0278(8) 0.0340(19) Uani 1 1 d . . . H10 H 0.4013 0.6588 0.0712 0.041 Uiso 1 1 calc R . . C11 C 0.4962(10) 0.7840(10) -0.1059(9) 0.046(2) Uani 1 1 d . . . H11 H 0.4368 0.7826 -0.1565 0.055 Uiso 1 1 calc R . . C12 C 0.6007(10) 0.8606(10) -0.1687(9) 0.044(2) Uani 1 1 d . . . H12 H 0.6102 0.9146 -0.2608 0.052 Uiso 1 1 calc R . . C13 C 0.6897(10) 0.8599(9) -0.1007(9) 0.045(2) Uani 1 1 d . . . H13 H 0.7649 0.9102 -0.1455 0.054 Uiso 1 1 calc R . . C14 C 0.6707(9) 0.7846(9) 0.0362(8) 0.0336(19) Uani 1 1 d . . . H14 H 0.7314 0.7856 0.0857 0.040 Uiso 1 1 calc R . . C15 C -0.0030(7) 0.5644(7) 0.5924(7) 0.0187(14) Uani 1 1 d . . . H15 H -0.0099 0.6100 0.6611 0.022 Uiso 1 1 calc R . . C16 C 0.1475(7) 0.4278(7) 0.4130(6) 0.0187(14) Uani 1 1 d . . . H16 H 0.2509 0.3736 0.3505 0.022 Uiso 1 1 calc R . . Cu1 Cu 0.37043(10) 0.48880(12) 0.50437(10) 0.0218(3) Uani 1 1 d . . . N1 N 0.1443(6) 0.4948(7) 0.5041(6) 0.0209(13) Uani 1 1 d . . . O1 O 0.2587(5) 0.6883(5) 0.5642(5) 0.0266(12) Uani 1 1 d . . . O2 O 0.4847(5) 0.7069(5) 0.5563(5) 0.0248(11) Uani 1 1 d . . . O3 O 0.6497(5) 0.6084(5) 0.3013(5) 0.0240(11) Uani 1 1 d . . . O4 O 0.4271(5) 0.5841(6) 0.3070(5) 0.0255(11) Uani 1 1 d . . . C1S C 0.8752(11) 0.3446(11) 0.0378(10) 0.071(3) Uani 1 1 d D . . H1S H 0.761(2) 0.379(8) 0.047(7) 0.107 Uiso 1 1 d D . . H2S H 0.924(8) 0.2372(12) 0.046(8) 0.107 Uiso 1 1 d D . . H3S H 0.934(8) 0.387(8) -0.052(4) 0.107 Uiso 1 1 d D . . H4S H 0.882(8) 0.376(8) 0.110(5) 0.107 Uiso 1 1 d 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 C1 0.022(3) 0.031(4) 0.015(3) 0.000(3) -0.006(3) -0.015(3) C2 0.025(3) 0.030(4) 0.009(3) 0.005(3) -0.002(3) -0.022(3) C3 0.018(3) 0.024(4) 0.030(4) 0.000(3) -0.008(3) -0.008(3) C4 0.018(4) 0.029(4) 0.037(5) -0.002(4) -0.001(3) -0.005(3) C5 0.041(5) 0.032(4) 0.025(4) 0.003(4) -0.011(3) -0.010(4) C6 0.058(5) 0.023(4) 0.021(4) 0.006(3) -0.021(4) -0.022(4) C7 0.025(4) 0.027(4) 0.028(4) 0.000(3) -0.011(3) -0.015(3) C8 0.014(3) 0.025(4) 0.030(4) -0.009(3) -0.009(3) -0.006(3) C9 0.022(3) 0.028(4) 0.020(4) -0.007(3) -0.001(3) -0.011(3) C10 0.033(4) 0.038(5) 0.035(5) 0.006(4) -0.020(4) -0.018(4) C11 0.053(5) 0.058(6) 0.036(5) 0.014(5) -0.030(4) -0.029(5) C12 0.052(5) 0.046(5) 0.031(5) 0.000(4) -0.011(4) -0.023(5) C13 0.052(5) 0.044(5) 0.045(6) 0.012(4) -0.022(4) -0.031(5) C14 0.037(4) 0.051(5) 0.022(4) 0.002(4) -0.011(3) -0.028(4) C15 0.025(3) 0.020(4) 0.019(4) -0.004(3) -0.006(3) -0.014(3) C16 0.022(3) 0.029(4) 0.007(3) -0.006(3) 0.005(2) -0.019(3) Cu1 0.0182(4) 0.0293(5) 0.0238(5) -0.0051(4) -0.0078(3) -0.0123(4) N1 0.017(3) 0.022(3) 0.016(3) -0.012(3) -0.003(2) 0.002(2) O1 0.021(2) 0.025(3) 0.035(3) -0.011(2) -0.007(2) -0.008(2) O2 0.020(2) 0.023(3) 0.030(3) -0.011(2) -0.007(2) -0.004(2) O3 0.027(2) 0.032(3) 0.020(3) -0.002(2) -0.008(2) -0.018(2) O4 0.026(2) 0.039(3) 0.017(3) 0.001(2) -0.008(2) -0.020(2) C1S 0.082(8) 0.063(7) 0.067(7) -0.015(6) -0.032(6) -0.016(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 C1 O2 1.253(7) . ? C1 O1 1.257(7) . ? C1 C2 1.514(9) . ? C2 C7 1.365(8) . ? C2 C3 1.397(8) . ? C3 C4 1.366(9) . ? C4 C5 1.388(10) . ? C5 C6 1.364(10) . ? C6 C7 1.402(9) . ? C8 O4 1.231(7) . ? C8 O3 1.272(7) . ? C8 C9 1.539(10) . ? C9 C14 1.362(10) . ? C9 C10 1.385(9) . ? C10 C11 1.362(10) . ? C11 C12 1.371(11) . ? C12 C13 1.342(10) . ? C13 C14 1.395(10) . ? C15 N1 1.327(7) . ? C15 C16 1.389(8) 2_566 ? C16 N1 1.337(7) . ? C16 C15 1.389(8) 2_566 ? Cu1 O2 1.953(4) 2_666 ? Cu1 O3 1.962(5) 2_666 ? Cu1 O4 1.968(5) . ? Cu1 O1 1.974(5) . ? Cu1 N1 2.163(5) . ? Cu1 Cu1 2.5797(17) 2_666 ? O2 Cu1 1.953(4) 2_666 ? O3 Cu1 1.962(5) 2_666 ? 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 C1 O1 126.8(6) . . ? O2 C1 C2 117.8(6) . . ? O1 C1 C2 115.4(5) . . ? C7 C2 C3 120.0(6) . . ? C7 C2 C1 119.5(6) . . ? C3 C2 C1 120.5(6) . . ? C4 C3 C2 121.1(7) . . ? C3 C4 C5 118.2(7) . . ? C6 C5 C4 121.9(7) . . ? C5 C6 C7 119.3(7) . . ? C2 C7 C6 119.6(6) . . ? O4 C8 O3 128.1(6) . . ? O4 C8 C9 115.7(5) . . ? O3 C8 C9 116.2(6) . . ? C14 C9 C10 119.7(7) . . ? C14 C9 C8 120.7(6) . . ? C10 C9 C8 119.6(6) . . ? C11 C10 C9 119.0(7) . . ? C10 C11 C12 121.1(7) . . ? C13 C12 C11 120.3(8) . . ? C12 C13 C14 119.4(8) . . ? C9 C14 C13 120.4(6) . . ? N1 C15 C16 121.6(5) . 2_566 ? N1 C16 C15 121.6(5) . 2_566 ? O2 Cu1 O3 88.6(2) 2_666 2_666 ? O2 Cu1 O4 89.5(2) 2_666 . ? O3 Cu1 O4 170.29(18) 2_666 . ? O2 Cu1 O1 170.19(18) 2_666 . ? O3 Cu1 O1 90.6(2) 2_666 . ? O4 Cu1 O1 89.6(2) . . ? O2 Cu1 N1 97.62(19) 2_666 . ? O3 Cu1 N1 97.9(2) 2_666 . ? O4 Cu1 N1 91.8(2) . . ? O1 Cu1 N1 92.17(19) . . ? O2 Cu1 Cu1 87.20(13) 2_666 2_666 ? O3 Cu1 Cu1 85.64(13) 2_666 2_666 ? O4 Cu1 Cu1 84.76(13) . 2_666 ? O1 Cu1 Cu1 82.99(13) . 2_666 ? N1 Cu1 Cu1 174.04(18) . 2_666 ? C15 N1 C16 116.8(5) . . ? C15 N1 Cu1 122.4(4) . . ? C16 N1 Cu1 120.8(4) . . ? C1 O1 Cu1 123.3(4) . . ? C1 O2 Cu1 119.7(4) . 2_666 ? C8 O3 Cu1 119.9(4) . 2_666 ? C8 O4 Cu1 121.5(4) . . ? 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 O2 C1 C2 C7 0.6(9) . . . . ? O1 C1 C2 C7 178.9(6) . . . . ? O2 C1 C2 C3 -178.6(6) . . . . ? O1 C1 C2 C3 -0.3(9) . . . . ? C7 C2 C3 C4 -1.7(10) . . . . ? C1 C2 C3 C4 177.5(6) . . . . ? C2 C3 C4 C5 0.1(11) . . . . ? C3 C4 C5 C6 1.0(11) . . . . ? C4 C5 C6 C7 -0.5(11) . . . . ? C3 C2 C7 C6 2.2(10) . . . . ? C1 C2 C7 C6 -177.0(6) . . . . ? C5 C6 C7 C2 -1.1(10) . . . . ? O4 C8 C9 C14 167.5(6) . . . . ? O3 C8 C9 C14 -11.7(10) . . . . ? O4 C8 C9 C10 -12.1(9) . . . . ? O3 C8 C9 C10 168.7(6) . . . . ? C14 C9 C10 C11 0.8(11) . . . . ? C8 C9 C10 C11 -179.7(7) . . . . ? C9 C10 C11 C12 -1.4(12) . . . . ? C10 C11 C12 C13 2.2(13) . . . . ? C11 C12 C13 C14 -2.2(13) . . . . ? C10 C9 C14 C13 -0.8(11) . . . . ? C8 C9 C14 C13 179.6(6) . . . . ? C12 C13 C14 C9 1.5(12) . . . . ? C16 C15 N1 C16 -2.4(11) 2_566 . . . ? C16 C15 N1 Cu1 177.4(5) 2_566 . . . ? C15 C16 N1 C15 2.4(11) 2_566 . . . ? C15 C16 N1 Cu1 -177.4(5) 2_566 . . . ? O2 Cu1 N1 C15 148.6(6) 2_666 . . . ? O3 Cu1 N1 C15 58.9(6) 2_666 . . . ? O4 Cu1 N1 C15 -121.7(6) . . . . ? O1 Cu1 N1 C15 -32.0(6) . . . . ? Cu1 Cu1 N1 C15 -67.7(18) 2_666 . . . ? O2 Cu1 N1 C16 -31.6(6) 2_666 . . . ? O3 Cu1 N1 C16 -121.3(5) 2_666 . . . ? O4 Cu1 N1 C16 58.1(5) . . . . ? O1 Cu1 N1 C16 147.8(5) . . . . ? Cu1 Cu1 N1 C16 112.1(15) 2_666 . . . ? O2 C1 O1 Cu1 -3.3(10) . . . . ? C2 C1 O1 Cu1 178.7(4) . . . . ? O2 Cu1 O1 C1 1.5(16) 2_666 . . . ? O3 Cu1 O1 C1 87.0(5) 2_666 . . . ? O4 Cu1 O1 C1 -83.3(5) . . . . ? N1 Cu1 O1 C1 -175.0(5) . . . . ? Cu1 Cu1 O1 C1 1.5(5) 2_666 . . . ? O1 C1 O2 Cu1 3.1(9) . . . 2_666 ? C2 C1 O2 Cu1 -178.8(4) . . . 2_666 ? O4 C8 O3 Cu1 -2.0(9) . . . 2_666 ? C9 C8 O3 Cu1 177.2(4) . . . 2_666 ? O3 C8 O4 Cu1 3.9(9) . . . . ? C9 C8 O4 Cu1 -175.2(4) . . . . ? O2 Cu1 O4 C8 -90.3(5) 2_666 . . . ? O3 Cu1 O4 C8 -11.6(16) 2_666 . . . ? O1 Cu1 O4 C8 80.0(5) . . . . ? N1 Cu1 O4 C8 172.1(5) . . . . ? Cu1 Cu1 O4 C8 -3.0(5) 2_666 . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.364 _refine_diff_density_min -1.002 _refine_diff_density_rms 0.138