# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Sally Brooker' _publ_contact_author_email Sbrooker@chemistry.otago.ac.nz _publ_author_name S.Brooker data_nw143 _database_code_depnum_ccdc_archive 'CCDC 751993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H60 Cu8 N20 O20' _chemical_formula_weight 1937.64 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 Tetragonal _symmetry_space_group_name_H-M P4(2)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 15.2873(12) _cell_length_b 15.2873(12) _cell_length_c 14.960(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3496.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 2542 _cell_measurement_theta_min 2.665 _cell_measurement_theta_max 22.906 _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 2.475 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.493 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SCALE (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19879 _diffrn_reflns_av_R_equivalents 0.1053 _diffrn_reflns_av_sigmaI/netI 0.1043 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3579 _reflns_number_gt 1653 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Two Cu in asym unit but cluster is Cu8. All non-H ANIS except disordered Me groups: one bridging acetate methyl group is disordered and modelled 0.5:0.5 as C34:C35. SAME C33 C34 and SAME C33 C35. Pyridyl ring involving C2 appears to be slightly disordered but this was not modelled as larger than usual ellipsoids considered to be best model of this. H's calc and ride except for bridging hydroxide which was found from a difference map, HIMP'ed to 0.85A and AFIX 01'ed. Q1 and Q2 are 1A from Cu. ; _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^)+(0.0609P)^2^+24.0683P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3579 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1782 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2039 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Cu1 Cu 0.86577(8) 0.66191(8) 0.10996(7) 0.0491(4) Uani 1 1 d . . . Cu2 Cu 0.94874(8) 0.65256(8) 0.30849(7) 0.0514(4) Uani 1 1 d . . . N1 N 0.8624(5) 0.6314(6) -0.0235(5) 0.057(2) Uani 1 1 d . . . C1 C 0.8747(9) 0.5539(9) -0.0570(7) 0.082(4) Uani 1 1 d . . . H1 H 0.8746 0.5047 -0.0182 0.098 Uiso 1 1 calc R . . C2 C 0.8886(11) 0.5407(11) -0.1507(8) 0.109(6) Uani 1 1 d . . . H2 H 0.8976 0.4835 -0.1736 0.131 Uiso 1 1 calc R . . C3 C 0.8886(9) 0.6110(10) -0.2064(9) 0.089(4) Uani 1 1 d . . . H3 H 0.8993 0.6039 -0.2685 0.107 Uiso 1 1 calc R . . C4 C 0.8726(8) 0.6939(9) -0.1703(7) 0.078(4) Uani 1 1 d . . . H4 H 0.8682 0.7441 -0.2075 0.093 Uiso 1 1 calc R . . C5 C 0.8633(6) 0.7002(8) -0.0786(6) 0.058(3) Uani 1 1 d . . . C6 C 0.8585(6) 0.7843(8) -0.0323(5) 0.053(3) Uani 1 1 d . . . N2 N 0.8515(5) 0.7839(6) 0.0591(4) 0.048(2) Uani 1 1 d . . . O1 O 0.8588(4) 0.6957(4) 0.2313(4) 0.0480(16) Uani 1 1 d . . . H1X H 0.8469 0.7483 0.2478 0.058 Uiso 1 1 d . . . O21 O 0.8413(5) 0.5389(5) 0.1371(4) 0.060(2) Uani 1 1 d . . . O22 O 0.9294(5) 0.5166(4) 0.2563(4) 0.0555(18) Uani 1 1 d . . . C23 C 0.8825(7) 0.4910(7) 0.1942(7) 0.057(3) Uani 1 1 d . . . C24 C 0.8705(8) 0.3934(7) 0.1809(7) 0.072(3) Uani 1 1 d . . . H24A H 0.9031 0.3616 0.2270 0.086 Uiso 1 1 calc R . . H24B H 0.8923 0.3768 0.1217 0.086 Uiso 1 1 calc R . . H24C H 0.8082 0.3788 0.1855 0.086 Uiso 1 1 calc R . . O31 O 1.0102(5) 0.6523(6) 0.0899(5) 0.073(2) Uani 1 1 d . A . O32 O 1.0502(5) 0.6783(5) 0.2315(5) 0.071(2) Uani 1 1 d . A . C33 C 1.0646(8) 0.6676(10) 0.1487(8) 0.082(4) Uani 1 1 d D . . C34 C 1.1622(12) 0.694(2) 0.1258(19) 0.077(8) Uiso 0.50 1 d PD A 1 H34A H 1.1760 0.6758 0.0646 0.093 Uiso 0.50 1 calc PR A 1 H34B H 1.2021 0.6649 0.1676 0.093 Uiso 0.50 1 calc PR A 1 H34C H 1.1689 0.7575 0.1310 0.093 Uiso 0.50 1 calc PR A 1 C35 C 1.1614(12) 0.6521(19) 0.1162(19) 0.074(8) Uiso 0.50 1 d PD A 2 H35A H 1.1632 0.6522 0.0507 0.089 Uiso 0.50 1 calc PR A 2 H35B H 1.1823 0.5955 0.1385 0.089 Uiso 0.50 1 calc PR A 2 H35C H 1.1991 0.6988 0.1392 0.089 Uiso 0.50 1 calc PR A 2 N3 N 0.8551(5) 0.8688(6) 0.0822(5) 0.047(2) Uani 1 1 d . . . C7 C 0.8634(6) 0.9142(8) 0.0050(6) 0.051(3) Uani 1 1 d . . . N5 N 0.8657(5) 0.8637(6) -0.0684(5) 0.056(2) Uani 1 1 d . . . C8 C 0.8817(7) 1.0066(8) 0.0103(6) 0.058(3) Uani 1 1 d . . . C9 C 0.9057(7) 1.0561(9) -0.0629(7) 0.068(3) Uani 1 1 d . . . H9 H 0.9079 1.0315 -0.1212 0.081 Uiso 1 1 calc R . . C10 C 0.9258(8) 1.1408(9) -0.0485(7) 0.077(4) Uani 1 1 d . . . H10 H 0.9443 1.1764 -0.0971 0.093 Uiso 1 1 calc R . . C11 C 0.9198(7) 1.1765(8) 0.0360(8) 0.070(3) Uani 1 1 d . . . H11 H 0.9328 1.2364 0.0463 0.084 Uiso 1 1 calc R . . C12 C 0.8947(7) 1.1227(8) 0.1050(7) 0.063(3) Uani 1 1 d . . . H12 H 0.8902 1.1469 0.1634 0.075 Uiso 1 1 calc R . . N4 N 0.8767(5) 1.0400(6) 0.0941(5) 0.055(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0534(8) 0.0706(9) 0.0232(5) 0.0004(5) -0.0031(5) 0.0154(7) Cu2 0.0643(9) 0.0618(9) 0.0280(5) 0.0076(6) -0.0101(6) 0.0007(7) N1 0.062(6) 0.077(6) 0.032(4) -0.007(4) 0.000(4) 0.026(5) C1 0.112(11) 0.093(10) 0.041(6) -0.012(6) 0.001(6) 0.030(8) C2 0.161(15) 0.116(12) 0.051(7) -0.033(8) 0.007(8) 0.071(11) C3 0.105(11) 0.104(11) 0.059(8) 0.014(8) -0.013(7) 0.008(9) C4 0.092(10) 0.103(11) 0.038(6) -0.007(6) 0.004(6) 0.022(8) C5 0.040(6) 0.104(9) 0.029(5) 0.005(6) 0.008(4) 0.021(6) C6 0.041(6) 0.102(9) 0.017(4) 0.004(5) 0.000(4) 0.016(6) N2 0.046(5) 0.079(6) 0.020(4) 0.007(4) 0.005(3) 0.018(5) O1 0.060(4) 0.061(4) 0.023(3) 0.002(3) -0.005(3) 0.000(3) O21 0.076(5) 0.070(5) 0.036(3) -0.006(3) -0.010(3) 0.018(4) O22 0.069(5) 0.068(5) 0.029(3) -0.001(3) -0.011(3) 0.009(4) C23 0.062(7) 0.068(8) 0.040(6) -0.004(6) 0.002(5) 0.013(6) C24 0.092(9) 0.062(8) 0.062(7) -0.026(6) -0.025(7) 0.013(7) O31 0.052(5) 0.118(7) 0.048(4) 0.014(4) -0.005(4) 0.019(5) O32 0.064(5) 0.100(6) 0.050(4) 0.024(4) -0.011(4) 0.001(4) C33 0.057(8) 0.129(12) 0.061(8) 0.023(8) -0.006(7) 0.026(8) N3 0.043(5) 0.070(6) 0.028(4) 0.005(4) 0.005(3) 0.009(5) C7 0.042(6) 0.083(8) 0.029(5) 0.020(5) 0.004(4) 0.004(6) N5 0.057(6) 0.087(7) 0.024(4) 0.008(4) 0.004(4) 0.011(5) C8 0.048(7) 0.091(9) 0.035(5) 0.014(6) 0.003(5) -0.001(6) C9 0.061(8) 0.096(10) 0.046(6) 0.034(6) 0.007(5) -0.001(7) C10 0.074(9) 0.109(11) 0.049(7) 0.034(7) 0.010(6) -0.018(8) C11 0.059(8) 0.082(9) 0.068(8) 0.024(7) 0.002(6) -0.012(6) C12 0.062(7) 0.080(9) 0.046(6) 0.015(6) 0.000(5) -0.012(6) N4 0.045(5) 0.076(7) 0.044(5) 0.009(5) -0.002(4) -0.003(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 Cu1 O1 1.891(6) . y Cu1 O21 1.960(8) . y Cu1 N2 2.026(9) . y Cu1 N1 2.050(8) . y Cu1 O31 2.233(7) . y Cu2 O1 1.912(6) . y Cu2 O32 1.972(8) . y Cu2 N3 2.045(8) 7_576 y Cu2 N4 2.066(9) 7_576 y Cu2 O22 2.240(7) . y N1 C1 1.299(14) . ? N1 C5 1.336(13) . ? C1 C2 1.432(15) . ? C1 H1 0.9500 . ? C2 C3 1.359(18) . ? C2 H2 0.9500 . ? C3 C4 1.400(17) . ? C3 H3 0.9500 . ? C4 C5 1.383(13) . ? C4 H4 0.9500 . ? C5 C6 1.463(15) . ? C6 N5 1.333(13) . ? C6 N2 1.372(10) . ? N2 N3 1.344(11) . ? O1 H1X 0.8607 . ? O21 C23 1.290(11) . ? O22 C23 1.237(11) . ? C23 C24 1.516(15) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O31 C33 1.233(13) . ? O32 C33 1.268(13) . ? C33 C35 1.58(2) . ? C33 C34 1.58(2) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? N3 C7 1.354(11) . ? N3 Cu2 2.045(8) 8_756 ? C7 N5 1.341(13) . ? C7 C8 1.443(15) . ? C8 N4 1.356(12) . ? C8 C9 1.381(13) . ? C9 C10 1.348(17) . ? C9 H9 0.9500 . ? C10 C11 1.380(16) . ? C10 H10 0.9500 . ? C11 C12 1.375(14) . ? C11 H11 0.9500 . ? C12 N4 1.304(13) . ? C12 H12 0.9500 . ? N4 Cu2 2.066(9) 8_756 ? 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 Cu1 O21 93.0(3) . . y O1 Cu1 N2 95.9(3) . . y O21 Cu1 N2 160.1(3) . . y O1 Cu1 N1 174.6(3) . . y O21 Cu1 N1 88.8(3) . . y N2 Cu1 N1 80.9(3) . . y O1 Cu1 O31 101.7(3) . . y O21 Cu1 O31 98.9(3) . . y N2 Cu1 O31 96.7(3) . . y N1 Cu1 O31 83.1(3) . . y O1 Cu2 O32 98.3(3) . . y O1 Cu2 N3 94.2(3) . 7_576 y O32 Cu2 N3 161.6(3) . 7_576 y O1 Cu2 N4 170.3(3) . 7_576 y O32 Cu2 N4 85.6(3) . 7_576 y N3 Cu2 N4 80.1(3) 7_576 7_576 y O1 Cu2 O22 90.9(3) . . y O32 Cu2 O22 94.9(3) . . y N3 Cu2 O22 98.4(3) 7_576 . y N4 Cu2 O22 97.7(3) 7_576 . y C1 N1 C5 118.5(9) . . ? C1 N1 Cu1 125.4(8) . . ? C5 N1 Cu1 114.9(7) . . ? N1 C1 C2 121.8(12) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.3(13) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.7(12) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 117.5(12) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 124.0(11) . . ? N1 C5 C6 113.6(8) . . ? C4 C5 C6 122.3(11) . . ? N5 C6 N2 114.5(10) . . ? N5 C6 C5 127.2(8) . . ? N2 C6 C5 118.1(10) . . ? N3 N2 C6 104.4(8) . . ? N3 N2 Cu1 142.0(5) . . ? C6 N2 Cu1 111.7(7) . . ? Cu1 O1 Cu2 116.4(3) . . y Cu1 O1 H1X 122.8 . . y Cu2 O1 H1X 107.6 . . y C23 O21 Cu1 126.1(7) . . ? C23 O22 Cu2 129.2(7) . . ? O22 C23 O21 126.9(10) . . ? O22 C23 C24 118.7(10) . . ? O21 C23 C24 114.3(9) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C33 O31 Cu1 123.9(7) . . ? C33 O32 Cu2 132.9(8) . . ? O31 C33 O32 127.2(11) . . ? O31 C33 C35 112.6(14) . . ? O32 C33 C35 118.9(14) . . ? O31 C33 C34 121.9(14) . . ? O32 C33 C34 110.0(15) . . ? C35 C33 C34 24.0(13) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N2 N3 C7 106.2(8) . . ? N2 N3 Cu2 141.3(6) . 8_756 ? C7 N3 Cu2 112.4(7) . 8_756 ? N5 C7 N3 113.9(10) . . ? N5 C7 C8 127.1(9) . . ? N3 C7 C8 118.2(9) . . ? C6 N5 C7 101.0(8) . . ? N4 C8 C9 122.8(12) . . ? N4 C8 C7 114.2(9) . . ? C9 C8 C7 123.0(10) . . ? C10 C9 C8 117.4(12) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? C9 C10 C11 120.7(11) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.1(12) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? N4 C12 C11 123.0(11) . . ? N4 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C12 N4 C8 118.0(10) . . ? C12 N4 Cu2 127.7(7) . 8_756 ? C8 N4 Cu2 114.2(8) . 8_756 ? 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 Cu1 N1 C1 -131(3) . . . . ? O21 Cu1 N1 C1 -22.3(10) . . . . ? N2 Cu1 N1 C1 174.7(11) . . . . ? O31 Cu1 N1 C1 76.8(10) . . . . ? O1 Cu1 N1 C5 61(4) . . . . ? O21 Cu1 N1 C5 170.4(7) . . . . ? N2 Cu1 N1 C5 7.4(7) . . . . ? O31 Cu1 N1 C5 -90.6(7) . . . . ? C5 N1 C1 C2 -0.4(19) . . . . ? Cu1 N1 C1 C2 -167.3(10) . . . . ? N1 C1 C2 C3 0(2) . . . . ? C1 C2 C3 C4 -2(2) . . . . ? C2 C3 C4 C5 4(2) . . . . ? C1 N1 C5 C4 3.2(17) . . . . ? Cu1 N1 C5 C4 171.5(9) . . . . ? C1 N1 C5 C6 -173.5(10) . . . . ? Cu1 N1 C5 C6 -5.3(11) . . . . ? C3 C4 C5 N1 -5.1(18) . . . . ? C3 C4 C5 C6 171.3(11) . . . . ? N1 C5 C6 N5 173.8(9) . . . . ? C4 C5 C6 N5 -3.0(16) . . . . ? N1 C5 C6 N2 -1.6(13) . . . . ? C4 C5 C6 N2 -178.4(10) . . . . ? N5 C6 N2 N3 -0.4(11) . . . . ? C5 C6 N2 N3 175.6(8) . . . . ? N5 C6 N2 Cu1 -168.4(6) . . . . ? C5 C6 N2 Cu1 7.6(11) . . . . ? O1 Cu1 N2 N3 15.7(10) . . . . ? O21 Cu1 N2 N3 131.9(10) . . . . ? N1 Cu1 N2 N3 -168.6(10) . . . . ? O31 Cu1 N2 N3 -86.8(10) . . . . ? O1 Cu1 N2 C6 176.5(6) . . . . ? O21 Cu1 N2 C6 -67.3(11) . . . . ? N1 Cu1 N2 C6 -7.8(7) . . . . ? O31 Cu1 N2 C6 74.0(7) . . . . ? O21 Cu1 O1 Cu2 67.5(4) . . . . ? N2 Cu1 O1 Cu2 -130.3(4) . . . . ? N1 Cu1 O1 Cu2 176(3) . . . . ? O31 Cu1 O1 Cu2 -32.2(4) . . . . ? O32 Cu2 O1 Cu1 46.1(4) . . . . ? N3 Cu2 O1 Cu1 -147.5(4) 7_576 . . . ? N4 Cu2 O1 Cu1 159.3(17) 7_576 . . . ? O22 Cu2 O1 Cu1 -49.0(4) . . . . ? O1 Cu1 O21 C23 -53.2(8) . . . . ? N2 Cu1 O21 C23 -169.8(8) . . . . ? N1 Cu1 O21 C23 131.9(8) . . . . ? O31 Cu1 O21 C23 49.2(8) . . . . ? O1 Cu2 O22 C23 6.4(9) . . . . ? O32 Cu2 O22 C23 -92.0(9) . . . . ? N3 Cu2 O22 C23 100.7(9) 7_576 . . . ? N4 Cu2 O22 C23 -178.2(9) 7_576 . . . ? Cu2 O22 C23 O21 9.3(16) . . . . ? Cu2 O22 C23 C24 -170.9(7) . . . . ? Cu1 O21 C23 O22 18.6(15) . . . . ? Cu1 O21 C23 C24 -161.2(7) . . . . ? O1 Cu1 O31 C33 -0.4(11) . . . . ? O21 Cu1 O31 C33 -95.4(10) . . . . ? N2 Cu1 O31 C33 97.1(11) . . . . ? N1 Cu1 O31 C33 177.0(11) . . . . ? O1 Cu2 O32 C33 -44.3(12) . . . . ? N3 Cu2 O32 C33 -176.4(11) 7_576 . . . ? N4 Cu2 O32 C33 144.7(12) 7_576 . . . ? O22 Cu2 O32 C33 47.3(12) . . . . ? Cu1 O31 C33 O32 11(2) . . . . ? Cu1 O31 C33 C35 177.9(13) . . . . ? Cu1 O31 C33 C34 -157.2(15) . . . . ? Cu2 O32 C33 O31 15(2) . . . . ? Cu2 O32 C33 C35 -150.9(14) . . . . ? Cu2 O32 C33 C34 -175.4(13) . . . . ? C6 N2 N3 C7 0.3(10) . . . . ? Cu1 N2 N3 C7 162.0(8) . . . . ? C6 N2 N3 Cu2 177.0(8) . . . 8_756 ? Cu1 N2 N3 Cu2 -21.4(16) . . . 8_756 ? N2 N3 C7 N5 -0.2(11) . . . . ? Cu2 N3 C7 N5 -177.9(6) 8_756 . . . ? N2 N3 C7 C8 -171.1(8) . . . . ? Cu2 N3 C7 C8 11.2(11) 8_756 . . . ? N2 C6 N5 C7 0.3(11) . . . . ? C5 C6 N5 C7 -175.2(9) . . . . ? N3 C7 N5 C6 -0.1(11) . . . . ? C8 C7 N5 C6 169.8(10) . . . . ? N5 C7 C8 N4 -178.1(9) . . . . ? N3 C7 C8 N4 -8.6(13) . . . . ? N5 C7 C8 C9 -0.6(17) . . . . ? N3 C7 C8 C9 168.9(9) . . . . ? N4 C8 C9 C10 0.9(17) . . . . ? C7 C8 C9 C10 -176.4(10) . . . . ? C8 C9 C10 C11 -1.9(18) . . . . ? C9 C10 C11 C12 1.4(18) . . . . ? C10 C11 C12 N4 0.3(18) . . . . ? C11 C12 N4 C8 -1.3(16) . . . . ? C11 C12 N4 Cu2 174.9(8) . . . 8_756 ? C9 C8 N4 C12 0.7(15) . . . . ? C7 C8 N4 C12 178.2(9) . . . . ? C9 C8 N4 Cu2 -176.0(8) . . . 8_756 ? C7 C8 N4 Cu2 1.5(11) . . . 8_756 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1X O1 0.86 1.84 2.689(9) 169.4 8_756 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.009 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.130 # Attachment 'jak569_orth.cif' data_jak569_orth _database_code_depnum_ccdc_archive 'CCDC 751994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H36 Cu4 N10 O11' _chemical_formula_weight 1014.89 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.973(3) _cell_length_b 12.682(2) _cell_length_c 20.506(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3893.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 91(2) _cell_measurement_reflns_used 1134 _cell_measurement_theta_min 2.327 _cell_measurement_theta_max 22.687 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 2.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5827 _exptl_absorpt_correction_T_max 0.8247 _exptl_absorpt_process_details 'SCALE(Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 91(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22176 _diffrn_reflns_av_R_equivalents 0.1370 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3984 _reflns_number_gt 2606 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+18.2867P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3984 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _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 Cu1 Cu -0.17613(5) 1.04231(6) 0.52889(4) 0.0182(2) Uani 1 1 d . A . Cu2 Cu -0.08361(6) 1.09318(7) 0.39445(4) 0.0189(2) Uani 1 1 d . A . N1 N -0.0821(4) 1.1717(4) 0.3081(3) 0.0202(13) Uani 1 1 d . . . N4 N -0.2781(4) 1.0605(4) 0.5934(2) 0.0180(12) Uani 1 1 d . . . N2 N 0.0476(4) 1.0765(4) 0.3706(3) 0.0190(13) Uani 1 1 d . . . N3 N -0.1234(4) 0.9720(4) 0.6092(3) 0.0195(12) Uani 1 1 d . . . N5 N -0.1503(4) 0.9076(4) 0.7098(3) 0.0204(13) Uani 1 1 d . . . C9 C -0.3319(4) 1.0194(5) 0.6999(3) 0.0196(15) Uani 1 1 d . . . H9 H -0.3234 0.9850 0.7406 0.024 Uiso 1 1 calc R . . C10 C -0.4096(5) 1.0757(5) 0.6874(3) 0.0234(16) Uani 1 1 d . . . H10 H -0.4549 1.0806 0.7197 0.028 Uiso 1 1 calc R . . C7 C -0.1811(5) 0.9612(5) 0.6580(3) 0.0180(14) Uani 1 1 d . . . C8 C -0.2669(4) 1.0145(5) 0.6518(3) 0.0173(14) Uani 1 1 d . . . C12 C -0.3527(5) 1.1170(5) 0.5824(3) 0.0226(16) Uani 1 1 d . . . H12 H -0.3588 1.1531 0.5421 0.027 Uiso 1 1 calc R . . C3 C -0.0664(5) 1.2647(6) 0.1862(3) 0.0287(18) Uani 1 1 d . . . H3 H -0.0620 1.2959 0.1442 0.034 Uiso 1 1 calc R . . C11 C -0.4206(5) 1.1246(6) 0.6274(4) 0.0255(17) Uani 1 1 d . . . H11 H -0.4737 1.1624 0.6177 0.031 Uiso 1 1 calc R . . C6 C 0.0661(4) 1.1133(5) 0.3110(3) 0.0178(14) Uani 1 1 d . . . C4 C 0.0077(5) 1.2158(6) 0.2147(3) 0.0260(17) Uani 1 1 d . . . H4 H 0.0638 1.2142 0.1930 0.031 Uiso 1 1 calc R . . C2 C -0.1449(6) 1.2668(6) 0.2194(3) 0.0313(19) Uani 1 1 d . . . H2 H -0.1955 1.3004 0.2007 0.038 Uiso 1 1 calc R . . C5 C -0.0031(5) 1.1704(6) 0.2749(3) 0.0256(16) Uani 1 1 d . . . C1 C -0.1515(5) 1.2204(6) 0.2801(3) 0.0267(17) Uani 1 1 d . . . H1 H -0.2069 1.2231 0.3026 0.032 Uiso 1 1 calc R . . O1 O -0.2718(3) 1.0293(4) 0.4625(2) 0.0281(12) Uani 1 1 d . . . O2 O -0.2035(3) 1.0432(4) 0.3661(2) 0.0244(11) Uani 1 1 d . . . C13 C -0.2706(5) 1.0207(6) 0.4004(3) 0.0221(15) Uani 1 1 d . . . C14 C -0.3538(5) 0.9879(7) 0.3679(3) 0.0303(18) Uani 1 1 d . . . H14A H -0.3484 0.9998 0.3208 0.045 Uiso 1 1 calc R . . H14B H -0.4039 1.0293 0.3850 0.045 Uiso 1 1 calc R . . H14C H -0.3645 0.9128 0.3762 0.045 Uiso 1 1 calc R . . O4 O -0.0859(3) 1.2394(4) 0.4424(2) 0.0233(11) Uani 1 1 d . . . O3 O -0.1390(3) 1.1998(4) 0.5414(2) 0.0253(11) Uani 1 1 d . . . C16 C -0.0693(5) 1.3660(5) 0.5275(3) 0.0255(16) Uani 1 1 d . . . H16A H -0.0851 1.3728 0.5737 0.038 Uiso 1 1 calc R . . H16B H -0.0986 1.4222 0.5026 0.038 Uiso 1 1 calc R . . H16C H -0.0044 1.3719 0.5225 0.038 Uiso 1 1 calc R . . C15 C -0.1001(5) 1.2597(6) 0.5024(3) 0.0221(16) Uani 1 1 d . . . O20 O -0.0828(3) 1.0008(4) 0.4696(2) 0.0189(10) Uani 1 1 d . . . C20 C -0.0903(10) 0.8884(13) 0.4538(7) 0.032(4) Uani 0.50 1 d P A 1 H20A H -0.1146 0.8504 0.4915 0.038 Uiso 0.50 1 calc PR A 1 H20B H -0.0312 0.8603 0.4431 0.038 Uiso 0.50 1 calc PR A 1 H20C H -0.1303 0.8793 0.4164 0.038 Uiso 0.50 1 calc PR A 1 H20X H -0.0314 1.0026 0.4895 0.038 Uiso 0.50 1 d P B 2 O30 O -0.0958(8) 0.7942(9) 0.4336(7) 0.053(4) Uani 0.50 1 d P C 2 H30X H -0.0923 0.8576 0.4474 0.064 Uiso 0.50 1 d P D 2 C30 C -0.1840(11) 0.7870(12) 0.4178(10) 0.045(5) Uani 0.50 1 d P C 2 H30A H -0.2047 0.7146 0.4247 0.054 Uiso 0.50 1 calc PR C 2 H30B H -0.1922 0.8063 0.3719 0.054 Uiso 0.50 1 calc PR C 2 H30C H -0.2186 0.8351 0.4454 0.054 Uiso 0.50 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0185(5) 0.0227(4) 0.0135(4) 0.0008(3) -0.0007(3) 0.0016(4) Cu2 0.0199(5) 0.0233(4) 0.0135(4) 0.0025(3) -0.0015(3) 0.0016(4) N1 0.018(3) 0.018(3) 0.025(3) -0.002(2) 0.000(3) 0.000(2) N4 0.020(3) 0.022(3) 0.013(3) -0.001(2) 0.000(2) 0.000(2) N2 0.021(3) 0.023(3) 0.013(3) 0.005(2) -0.002(2) 0.006(2) N3 0.020(3) 0.021(3) 0.017(3) 0.005(2) 0.003(2) 0.004(2) N5 0.024(3) 0.022(3) 0.016(3) 0.001(2) 0.000(2) -0.004(3) C9 0.019(4) 0.022(4) 0.018(3) 0.001(3) 0.003(3) -0.002(3) C10 0.023(4) 0.020(4) 0.027(4) -0.003(3) 0.009(3) -0.004(3) C7 0.023(4) 0.022(3) 0.009(3) -0.006(3) 0.000(3) -0.005(3) C8 0.016(4) 0.022(3) 0.014(3) -0.004(3) 0.000(3) -0.004(3) C12 0.023(4) 0.025(4) 0.020(3) -0.007(3) -0.002(3) 0.001(3) C3 0.041(5) 0.032(4) 0.014(3) 0.003(3) -0.004(3) 0.011(4) C11 0.012(4) 0.025(4) 0.039(4) -0.015(3) 0.002(3) 0.001(3) C6 0.014(4) 0.022(3) 0.018(3) 0.002(3) -0.003(3) 0.004(3) C4 0.026(4) 0.026(4) 0.025(4) 0.002(3) -0.001(3) -0.004(3) C2 0.051(5) 0.020(4) 0.022(4) 0.004(3) -0.005(4) 0.011(4) C5 0.028(4) 0.025(4) 0.024(4) 0.000(3) -0.007(3) 0.002(3) C1 0.031(5) 0.028(4) 0.021(4) -0.003(3) -0.006(3) 0.006(3) O1 0.016(3) 0.048(3) 0.020(3) 0.001(2) -0.003(2) -0.001(2) O2 0.020(3) 0.035(3) 0.018(2) 0.006(2) -0.003(2) -0.001(2) C13 0.018(4) 0.030(4) 0.019(3) 0.001(3) -0.006(3) -0.001(3) C14 0.025(4) 0.052(5) 0.014(3) 0.005(3) -0.006(3) -0.003(4) O4 0.030(3) 0.024(3) 0.016(2) 0.000(2) 0.006(2) -0.001(2) O3 0.029(3) 0.031(3) 0.016(2) -0.004(2) 0.002(2) -0.005(2) C16 0.036(5) 0.021(4) 0.019(3) 0.002(3) 0.002(3) 0.004(3) C15 0.022(4) 0.025(4) 0.019(3) 0.005(3) -0.001(3) 0.007(3) O20 0.015(2) 0.026(3) 0.016(2) 0.002(2) -0.0031(19) 0.001(2) C20 0.029(9) 0.049(10) 0.018(7) -0.009(7) -0.007(7) 0.008(8) O30 0.041(8) 0.031(7) 0.088(10) -0.034(7) -0.017(7) 0.008(6) C30 0.035(11) 0.021(8) 0.080(13) 0.001(9) -0.011(10) -0.008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O20 1.926(5) . y Cu1 O1 1.982(5) . y Cu1 N3 2.032(5) . y Cu1 N4 2.034(5) . y Cu1 O3 2.089(5) . y Cu2 O20 1.935(4) . y Cu2 O2 1.990(5) . y Cu2 N1 2.031(6) . y Cu2 N2 2.035(6) . y Cu2 O4 2.100(5) . y N1 C1 1.339(9) . ? N1 C5 1.365(9) . ? N4 C8 1.341(8) . ? N4 C12 1.347(9) . ? N2 C6 1.336(8) . ? N2 N3 1.357(8) 5_576 ? N3 C7 1.330(8) . ? N3 N2 1.357(8) 5_576 ? N5 C7 1.343(8) . ? N5 C6 1.357(8) 5_576 ? C9 C8 1.387(9) . ? C9 C10 1.389(10) . ? C9 H9 0.9500 . ? C10 C11 1.388(10) . ? C10 H10 0.9500 . ? C7 C8 1.457(9) . ? C12 C11 1.376(10) . ? C12 H12 0.9500 . ? C3 C2 1.358(11) . ? C3 C4 1.399(10) . ? C3 H3 0.9500 . ? C11 H11 0.9500 . ? C6 N5 1.357(8) 5_576 ? C6 C5 1.465(9) . ? C4 C5 1.372(9) . ? C4 H4 0.9500 . ? C2 C1 1.381(9) . ? C2 H2 0.9500 . ? C1 H1 0.9500 . ? O1 C13 1.279(8) . ? O2 C13 1.259(8) . ? C13 C14 1.473(9) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O4 C15 1.274(8) . ? O3 C15 1.247(8) . ? C16 C15 1.515(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O20 C20 1.466(16) . ? O20 H20X 0.8722 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C20 H30X 0.4133 . ? O30 C30 1.364(18) . ? O30 H30X 0.8539 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O20 Cu1 O1 93.89(19) . . y O20 Cu1 N3 96.3(2) . . y O1 Cu1 N3 143.2(2) . . y O20 Cu1 N4 170.7(2) . . y O1 Cu1 N4 85.1(2) . . y N3 Cu1 N4 79.3(2) . . y O20 Cu1 O3 98.36(19) . . y O1 Cu1 O3 110.9(2) . . y N3 Cu1 O3 102.5(2) . . y N4 Cu1 O3 90.7(2) . . y O20 Cu2 O2 92.58(19) . . y O20 Cu2 N1 172.1(2) . . y O2 Cu2 N1 85.0(2) . . y O20 Cu2 N2 97.1(2) . . y O2 Cu2 N2 140.1(2) . . y N1 Cu2 N2 80.2(2) . . y O20 Cu2 O4 99.30(18) . . y O2 Cu2 O4 113.8(2) . . y N1 Cu2 O4 88.57(19) . . y N2 Cu2 O4 102.7(2) . . y C1 N1 C5 117.7(6) . . ? C1 N1 Cu2 126.2(5) . . ? C5 N1 Cu2 116.0(4) . . ? C8 N4 C12 119.0(6) . . ? C8 N4 Cu1 115.9(4) . . ? C12 N4 Cu1 125.1(4) . . ? C6 N2 N3 105.3(5) . 5_576 ? C6 N2 Cu2 112.6(4) . . ? N3 N2 Cu2 141.4(4) 5_576 . ? C7 N3 N2 105.5(5) . 5_576 ? C7 N3 Cu1 113.8(5) . . ? N2 N3 Cu1 140.5(4) 5_576 . ? C7 N5 C6 99.7(5) . 5_576 ? C8 C9 C10 118.7(6) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 119.5(6) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N3 C7 N5 115.1(6) . . ? N3 C7 C8 117.3(6) . . ? N5 C7 C8 127.4(6) . . ? N4 C8 C9 121.8(6) . . ? N4 C8 C7 113.0(6) . . ? C9 C8 C7 125.2(6) . . ? N4 C12 C11 122.5(7) . . ? N4 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C2 C3 C4 119.0(7) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C12 C11 C10 118.4(7) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? N2 C6 N5 114.4(6) . 5_576 ? N2 C6 C5 119.2(6) . . ? N5 C6 C5 126.5(6) 5_576 . ? C5 C4 C3 117.9(7) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C3 C2 C1 120.4(7) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? N1 C5 C4 123.1(7) . . ? N1 C5 C6 111.5(6) . . ? C4 C5 C6 125.4(7) . . ? N1 C1 C2 121.8(7) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C13 O1 Cu1 132.9(5) . . ? C13 O2 Cu2 129.0(4) . . ? O2 C13 O1 123.2(6) . . ? O2 C13 C14 119.1(6) . . ? O1 C13 C14 117.6(6) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 O4 Cu2 129.3(4) . . ? C15 O3 Cu1 128.9(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C15 O4 125.0(7) . . ? O3 C15 C16 117.8(6) . . ? O4 C15 C16 117.2(6) . . ? C20 O20 Cu1 110.4(7) . . ? C20 O20 Cu2 114.4(6) . . ? Cu1 O20 Cu2 109.5(2) . . ? C20 O20 H20X 101.3 . . ? Cu1 O20 H20X 109.7 . . ? Cu2 O20 H20X 111.3 . . ? O20 C20 H20A 109.5 . . ? O20 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O20 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O20 C20 H30X 174.2 . . ? H20A C20 H30X 76.1 . . ? H20B C20 H30X 69.4 . . ? H20C C20 H30X 66.3 . . ? C30 O30 H30X 101.6 . . ? O30 C30 H30A 109.5 . . ? O30 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O30 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? 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 O20 Cu2 N1 C1 110.9(15) . . . . ? O2 Cu2 N1 C1 38.7(6) . . . . ? N2 Cu2 N1 C1 -178.5(6) . . . . ? O4 Cu2 N1 C1 -75.3(6) . . . . ? O20 Cu2 N1 C5 -66.3(17) . . . . ? O2 Cu2 N1 C5 -138.5(5) . . . . ? N2 Cu2 N1 C5 4.3(5) . . . . ? O4 Cu2 N1 C5 107.5(5) . . . . ? O20 Cu1 N4 C8 57.8(14) . . . . ? O1 Cu1 N4 C8 141.8(5) . . . . ? N3 Cu1 N4 C8 -4.7(5) . . . . ? O3 Cu1 N4 C8 -107.3(5) . . . . ? O20 Cu1 N4 C12 -124.3(12) . . . . ? O1 Cu1 N4 C12 -40.4(6) . . . . ? N3 Cu1 N4 C12 173.1(6) . . . . ? O3 Cu1 N4 C12 70.5(5) . . . . ? O20 Cu2 N2 C6 166.3(5) . . . . ? O2 Cu2 N2 C6 63.7(6) . . . . ? N1 Cu2 N2 C6 -6.2(5) . . . . ? O4 Cu2 N2 C6 -92.5(5) . . . . ? O20 Cu2 N2 N3 -1.9(7) . . . 5_576 ? O2 Cu2 N2 N3 -104.5(7) . . . 5_576 ? N1 Cu2 N2 N3 -174.3(7) . . . 5_576 ? O4 Cu2 N2 N3 99.4(7) . . . 5_576 ? O20 Cu1 N3 C7 -164.1(5) . . . . ? O1 Cu1 N3 C7 -58.9(6) . . . . ? N4 Cu1 N3 C7 7.6(5) . . . . ? O3 Cu1 N3 C7 95.9(5) . . . . ? O20 Cu1 N3 N2 9.5(7) . . . 5_576 ? O1 Cu1 N3 N2 114.7(7) . . . 5_576 ? N4 Cu1 N3 N2 -178.8(7) . . . 5_576 ? O3 Cu1 N3 N2 -90.6(7) . . . 5_576 ? C8 C9 C10 C11 0.5(10) . . . . ? N2 N3 C7 N5 -0.8(8) 5_576 . . . ? Cu1 N3 C7 N5 174.9(4) . . . . ? N2 N3 C7 C8 174.8(5) 5_576 . . . ? Cu1 N3 C7 C8 -9.4(7) . . . . ? C6 N5 C7 N3 0.9(7) 5_576 . . . ? C6 N5 C7 C8 -174.2(7) 5_576 . . . ? C12 N4 C8 C9 3.1(10) . . . . ? Cu1 N4 C8 C9 -179.0(5) . . . . ? C12 N4 C8 C7 -176.7(6) . . . . ? Cu1 N4 C8 C7 1.3(7) . . . . ? C10 C9 C8 N4 -1.4(10) . . . . ? C10 C9 C8 C7 178.3(6) . . . . ? N3 C7 C8 N4 5.5(9) . . . . ? N5 C7 C8 N4 -179.5(6) . . . . ? N3 C7 C8 C9 -174.2(6) . . . . ? N5 C7 C8 C9 0.7(11) . . . . ? C8 N4 C12 C11 -3.8(10) . . . . ? Cu1 N4 C12 C11 178.4(5) . . . . ? N4 C12 C11 C10 2.8(10) . . . . ? C9 C10 C11 C12 -1.1(10) . . . . ? N3 N2 C6 N5 -0.2(8) 5_576 . . 5_576 ? Cu2 N2 C6 N5 -172.5(4) . . . 5_576 ? N3 N2 C6 C5 179.8(6) 5_576 . . . ? Cu2 N2 C6 C5 7.4(8) . . . . ? C2 C3 C4 C5 1.1(11) . . . . ? C4 C3 C2 C1 -0.7(11) . . . . ? C1 N1 C5 C4 -0.4(10) . . . . ? Cu2 N1 C5 C4 177.1(6) . . . . ? C1 N1 C5 C6 -179.2(6) . . . . ? Cu2 N1 C5 C6 -1.7(7) . . . . ? C3 C4 C5 N1 -0.6(11) . . . . ? C3 C4 C5 C6 178.0(7) . . . . ? N2 C6 C5 N1 -3.9(9) . . . . ? N5 C6 C5 N1 176.0(6) 5_576 . . . ? N2 C6 C5 C4 177.3(7) . . . . ? N5 C6 C5 C4 -2.7(12) 5_576 . . . ? C5 N1 C1 C2 0.9(10) . . . . ? Cu2 N1 C1 C2 -176.3(5) . . . . ? C3 C2 C1 N1 -0.4(11) . . . . ? O20 Cu1 O1 C13 -14.0(7) . . . . ? N3 Cu1 O1 C13 -120.0(7) . . . . ? N4 Cu1 O1 C13 175.3(7) . . . . ? O3 Cu1 O1 C13 86.5(7) . . . . ? O20 Cu2 O2 C13 38.8(6) . . . . ? N1 Cu2 O2 C13 -148.7(6) . . . . ? N2 Cu2 O2 C13 143.1(6) . . . . ? O4 Cu2 O2 C13 -62.5(6) . . . . ? Cu2 O2 C13 O1 1.4(11) . . . . ? Cu2 O2 C13 C14 178.2(5) . . . . ? Cu1 O1 C13 O2 -17.2(11) . . . . ? Cu1 O1 C13 C14 166.0(5) . . . . ? O20 Cu2 O4 C15 -11.9(6) . . . . ? O2 Cu2 O4 C15 85.1(6) . . . . ? N1 Cu2 O4 C15 169.0(6) . . . . ? N2 Cu2 O4 C15 -111.4(6) . . . . ? O20 Cu1 O3 C15 29.8(6) . . . . ? O1 Cu1 O3 C15 -67.7(6) . . . . ? N3 Cu1 O3 C15 128.2(6) . . . . ? N4 Cu1 O3 C15 -152.6(6) . . . . ? Cu1 O3 C15 O4 10.2(10) . . . . ? Cu1 O3 C15 C16 -171.4(4) . . . . ? Cu2 O4 C15 O3 -20.6(10) . . . . ? Cu2 O4 C15 C16 161.0(5) . . . . ? O1 Cu1 O20 C20 -70.6(7) . . . . ? N3 Cu1 O20 C20 74.0(7) . . . . ? N4 Cu1 O20 C20 12.6(15) . . . . ? O3 Cu1 O20 C20 177.7(6) . . . . ? O1 Cu1 O20 Cu2 56.2(3) . . . . ? N3 Cu1 O20 Cu2 -159.2(2) . . . . ? N4 Cu1 O20 Cu2 139.4(11) . . . . ? O3 Cu1 O20 Cu2 -55.6(2) . . . . ? O2 Cu2 O20 C20 59.5(7) . . . . ? N1 Cu2 O20 C20 -12.2(18) . . . . ? N2 Cu2 O20 C20 -81.7(7) . . . . ? O4 Cu2 O20 C20 174.1(7) . . . . ? O2 Cu2 O20 Cu1 -65.0(2) . . . . ? N1 Cu2 O20 Cu1 -136.7(15) . . . . ? N2 Cu2 O20 Cu1 153.8(2) . . . . ? O4 Cu2 O20 Cu1 49.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O30 H30X O20 0.85 1.88 2.729(12) 174.6 . O20 H20X O20 0.87 1.91 2.777(9) 176.7 5_576 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.937 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.157