# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Anastasios Keramidas' _publ_contact_author_email AKERAMID@UCY.AC.CY _publ_section_title ; Synthesis, structure, magnetic properties and aqueous solution characterization, of p-hydroquinone and phenol iminodiacetate copper (II) complexes ; loop_ _publ_author_name 'Anastasios Keramidas' 'Chryssoula Drouza' 'John Giapintzakis' 'Marios Stylianou' ; Z.Viskadourakis ; # Attachment 'Cu1_complex.cif' data_Cu1 _database_code_depnum_ccdc_archive 'CCDC 680992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 Cu N O11' _chemical_formula_weight 416.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.0596(13) _cell_length_b 10.4096(11) _cell_length_c 14.4704(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.112(10) _cell_angle_gamma 90.00 _cell_volume 1592.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.359 _exptl_crystal_size_mid 0.255 _exptl_crystal_size_min 0.103 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 1.433 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 5647 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.1192 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 30.37 _reflns_number_total 3987 _reflns_number_gt 2295 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0643P)^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 3987 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _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 Cu Cu 0.85396(4) 0.92494(4) 0.63279(3) 0.01017(14) Uani 1 1 d . . . O5 O 0.5630(2) 0.8723(3) 0.73312(18) 0.0133(6) Uani 1 1 d . . . O4 O 0.9692(2) 1.2519(2) 0.55645(18) 0.0126(6) Uani 1 1 d . . . O4W O 1.3984(3) 1.0405(3) 0.7904(2) 0.0199(7) Uani 1 1 d . . . O6 O 0.6844(3) 0.9619(3) 1.05629(19) 0.0182(6) Uani 1 1 d . . . H6 H 0.6498 0.9571 1.0991 0.027 Uiso 1 1 calc R . . O1W O 0.9095(2) 0.7721(2) 0.57684(18) 0.0121(6) Uani 1 1 d . . . O1 O 1.0264(2) 0.8693(3) 0.78588(18) 0.0154(6) Uani 1 1 d . . . H1 H 1.0638 0.8012 0.7859 0.023 Uiso 1 1 calc R . . O3W O 1.2087(3) 0.9354(3) 0.6404(2) 0.0162(6) Uani 1 1 d . . . O3 O 0.7278(2) 0.8325(2) 0.67955(18) 0.0123(6) Uani 1 1 d . . . O2W O 0.6842(2) 0.9722(3) 0.49575(19) 0.0159(6) Uani 1 1 d . . . O7 O 0.7931(2) 0.7930(3) 1.13447(19) 0.0183(6) Uani 1 1 d . . . O2 O 0.9659(2) 1.0451(2) 0.59509(18) 0.0112(6) Uani 1 1 d . . . N N 0.8106(3) 1.0758(3) 0.7016(2) 0.0076(6) Uani 1 1 d . . . C9 C 0.8246(4) 1.1874(4) 0.6409(3) 0.0121(8) Uani 1 1 d . . . H9A H 0.8448 1.2640 0.6806 0.015 Uiso 1 1 calc R . . H9B H 0.7455 1.2022 0.5908 0.015 Uiso 1 1 calc R . . C5 C 0.8349(3) 0.9779(4) 0.9342(3) 0.0123(8) Uani 1 1 d . . . H5 H 0.7880 1.0498 0.9405 0.015 Uiso 1 1 calc R . . C4 C 0.8396(3) 0.8715(4) 0.9943(3) 0.0118(8) Uani 1 1 d . . . C2 C 0.9758(3) 0.7627(4) 0.9179(3) 0.0137(8) Uani 1 1 d . . . H2 H 1.0234 0.6911 0.9122 0.016 Uiso 1 1 calc R . . C12 C 0.6561(3) 0.9096(4) 0.7080(3) 0.0099(8) Uani 1 1 d . . . C10 C 0.9294(3) 1.1604(4) 0.5949(3) 0.0107(8) Uani 1 1 d . . . C3 C 0.9117(3) 0.7661(4) 0.9867(3) 0.0138(8) Uani 1 1 d . . . H3 H 0.9172 0.6967 1.0282 0.017 Uiso 1 1 calc R . . C11 C 0.6801(3) 1.0522(3) 0.7047(3) 0.0103(8) Uani 1 1 d . . . H11A H 0.6204 1.0893 0.6479 0.012 Uiso 1 1 calc R . . H11B H 0.6677 1.0933 0.7614 0.012 Uiso 1 1 calc R . . C7 C 0.7715(3) 0.8704(4) 1.0688(3) 0.0122(8) Uani 1 1 d . . . C1 C 0.9681(3) 0.8672(4) 0.8578(3) 0.0126(8) Uani 1 1 d . . . C8 C 0.8985(3) 1.0916(3) 0.8015(2) 0.0101(8) Uani 1 1 d . . . H8A H 0.8736 1.1670 0.8309 0.012 Uiso 1 1 calc R . . H8B H 0.9834 1.1061 0.7975 0.012 Uiso 1 1 calc R . . C6 C 0.8997(3) 0.9772(4) 0.8650(3) 0.0105(8) Uani 1 1 d . . . H3WA H 1.134(4) 0.962(4) 0.629(3) 0.014(12) Uiso 1 1 d . . . H4WA H 1.459(4) 0.998(4) 0.793(3) 0.009(12) Uiso 1 1 d . . . H3WB H 1.202(4) 0.866(5) 0.643(3) 0.018(15) Uiso 1 1 d . . . H4WB H 1.336(5) 1.006(6) 0.754(4) 0.050(19) Uiso 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 Cu 0.0118(2) 0.0103(2) 0.0100(2) -0.0009(2) 0.00574(17) -0.0007(2) O5 0.0116(13) 0.0148(14) 0.0168(15) -0.0017(11) 0.0092(11) -0.0037(11) O4 0.0137(14) 0.0128(14) 0.0129(14) 0.0014(11) 0.0065(11) -0.0022(11) O4W 0.0194(18) 0.0196(17) 0.0224(19) 0.0016(14) 0.0089(15) 0.0040(15) O6 0.0231(15) 0.0220(16) 0.0142(15) 0.0045(12) 0.0127(12) 0.0057(13) O1W 0.0121(14) 0.0109(13) 0.0158(14) -0.0025(11) 0.0082(11) 0.0006(11) O1 0.0172(14) 0.0153(14) 0.0161(16) 0.0023(12) 0.0089(12) 0.0067(12) O3W 0.0144(16) 0.0162(18) 0.0187(16) 0.0038(14) 0.0061(12) 0.0040(14) O3 0.0101(13) 0.0111(13) 0.0173(15) 0.0004(11) 0.0065(11) 0.0003(11) O2W 0.0163(14) 0.0181(14) 0.0143(15) -0.0001(12) 0.0060(12) -0.0003(12) O7 0.0184(15) 0.0235(16) 0.0145(15) 0.0070(12) 0.0072(12) -0.0001(13) O2 0.0099(13) 0.0108(14) 0.0151(14) -0.0010(11) 0.0069(11) 0.0000(10) N 0.0078(14) 0.0100(15) 0.0052(15) -0.0003(13) 0.0024(12) -0.0005(14) C9 0.016(2) 0.0121(19) 0.008(2) 0.0031(16) 0.0035(16) 0.0045(16) C5 0.0112(19) 0.0136(19) 0.010(2) -0.0034(16) 0.0003(16) 0.0013(16) C4 0.0130(19) 0.0166(19) 0.0048(19) -0.0022(16) 0.0012(15) -0.0039(17) C2 0.014(2) 0.0126(19) 0.013(2) -0.0033(16) 0.0018(16) 0.0032(16) C12 0.0110(18) 0.0110(19) 0.0067(19) 0.0019(15) 0.0009(14) -0.0012(15) C10 0.0081(18) 0.016(2) 0.007(2) -0.0014(15) 0.0009(15) -0.0021(16) C3 0.015(2) 0.0129(19) 0.013(2) 0.0009(16) 0.0031(16) -0.0001(17) C11 0.0091(18) 0.012(2) 0.0088(19) 0.0004(15) 0.0017(14) -0.0017(15) C7 0.0118(19) 0.016(2) 0.008(2) -0.0028(16) 0.0018(15) -0.0047(17) C1 0.0115(19) 0.017(2) 0.009(2) -0.0043(16) 0.0027(15) -0.0031(17) C8 0.0094(18) 0.013(2) 0.0089(19) 0.0018(15) 0.0041(14) 0.0017(16) C6 0.0106(19) 0.0112(18) 0.009(2) 0.0004(15) 0.0020(15) -0.0004(16) _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 Cu O2 1.948(2) . ? Cu O1W 1.963(2) . ? Cu O3 1.972(2) . ? Cu N 1.991(3) . ? Cu O2W 2.347(3) . ? O5 C12 1.251(4) . ? O4 C10 1.247(4) . ? O6 C7 1.329(5) . ? O1 C1 1.376(4) . ? O3 C12 1.278(4) . ? O7 C7 1.215(5) . ? O2 C10 1.267(4) . ? N C11 1.478(4) . ? N C9 1.492(5) . ? N C8 1.494(5) . ? C9 C10 1.522(5) . ? C5 C6 1.391(5) . ? C5 C4 1.401(5) . ? C4 C3 1.379(5) . ? C4 C7 1.485(5) . ? C2 C1 1.380(5) . ? C2 C3 1.382(5) . ? C12 C11 1.512(5) . ? C1 C6 1.393(5) . ? C8 C6 1.503(5) . ? 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 Cu O1W 95.91(11) . . ? O2 Cu O3 169.20(11) . . ? O1W Cu O3 94.85(11) . . ? O2 Cu N 84.27(11) . . ? O1W Cu N 174.37(11) . . ? O3 Cu N 85.11(11) . . ? O2 Cu O2W 92.57(10) . . ? O1W Cu O2W 95.22(10) . . ? O3 Cu O2W 85.50(10) . . ? N Cu O2W 90.39(11) . . ? C12 O3 Cu 111.9(2) . . ? C10 O2 Cu 112.4(2) . . ? C11 N C9 114.8(3) . . ? C11 N C8 110.6(3) . . ? C9 N C8 109.5(3) . . ? C11 N Cu 105.4(2) . . ? C9 N Cu 103.7(2) . . ? C8 N Cu 112.7(2) . . ? N C9 C10 109.8(3) . . ? C6 C5 C4 120.7(4) . . ? C3 C4 C5 119.7(3) . . ? C3 C4 C7 118.7(4) . . ? C5 C4 C7 121.6(4) . . ? C1 C2 C3 119.0(4) . . ? O5 C12 O3 122.7(3) . . ? O5 C12 C11 118.8(3) . . ? O3 C12 C11 118.4(3) . . ? O4 C10 O2 124.8(3) . . ? O4 C10 C9 118.0(3) . . ? O2 C10 C9 117.2(3) . . ? C4 C3 C2 120.5(4) . . ? N C11 C12 110.3(3) . . ? O7 C7 O6 123.4(3) . . ? O7 C7 C4 123.2(4) . . ? O6 C7 C4 113.4(3) . . ? O1 C1 C2 122.3(3) . . ? O1 C1 C6 115.4(3) . . ? C2 C1 C6 122.3(3) . . ? N C8 C6 113.0(3) . . ? C5 C6 C1 117.7(3) . . ? C5 C6 C8 121.5(3) . . ? C1 C6 C8 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 30.37 _diffrn_measured_fraction_theta_full 0.829 _refine_diff_density_max 0.898 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.129 # Attachment 'Cu3_complex.cif' data_Cu3 _database_code_depnum_ccdc_archive 'CCDC 680993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 Cu N O6' _chemical_formula_weight 277.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.4039(8) _cell_length_b 7.0659(4) _cell_length_c 12.9051(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.217(6) _cell_angle_gamma 90.00 _cell_volume 981.93(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.534 _exptl_crystal_size_mid 0.278 _exptl_crystal_size_min 0.164 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.878 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.237 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.479 _exptl_absorpt_correction_T_max 0.693 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 14792 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 31.26 _reflns_number_total 3014 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0578P)^2^+0.1538P] 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 3014 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.003 _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 N N 0.32322(15) 0.7908(2) 0.72740(13) 0.0086(3) Uani 1 1 d . . . O4 O 0.35157(17) 0.51593(18) 0.49946(14) 0.0154(3) Uani 1 1 d . . . O3 O 0.31269(14) 1.1737(2) 0.72974(12) 0.0135(3) Uani 1 1 d . . . O2 O 0.42309(14) 0.8022(2) 0.56576(12) 0.0129(3) Uani 1 1 d . . . C7 C 0.21691(19) 0.8799(3) 0.75091(18) 0.0126(4) Uani 1 1 d . . . C8 C 0.2360(2) 1.0922(3) 0.76907(17) 0.0144(4) Uani 1 1 d . . . O5 O 0.17271(17) 1.1707(2) 0.81746(14) 0.0245(4) Uani 1 1 d . . . C5 C 0.28732(19) 0.6370(3) 0.64423(17) 0.0126(4) Uani 1 1 d . . . C6 C 0.35935(18) 0.6495(3) 0.56369(16) 0.0122(4) Uani 1 1 d . . . C4 C 0.41547(19) 0.7126(3) 0.83086(16) 0.0113(4) Uani 1 1 d . . . C2 C 0.46018(18) 0.8600(3) 0.91892(16) 0.0120(4) Uani 1 1 d . . . O1 O 0.57488(16) 1.00218(19) 0.81591(13) 0.0119(3) Uani 1 1 d . . . C1 C 0.5401(2) 1.0036(2) 0.90883(17) 0.0100(4) Uani 1 1 d . . . C3 C 0.42061(19) 0.8580(3) 1.01066(16) 0.0124(4) Uani 1 1 d . . . H3 H 0.3674 0.7629 1.0178 0.015 Uiso 1 1 calc R . . O1W O 0.46276(14) 1.1974(2) 0.59136(12) 0.0152(3) Uani 1 1 d . . . H7A H 0.202(2) 0.827(3) 0.8109(19) 0.008(6) Uiso 1 1 d . . . H7B H 0.144(2) 0.873(3) 0.6888(18) 0.009(5) Uiso 1 1 d . . . H4A H 0.379(2) 0.612(3) 0.8551(17) 0.004(5) Uiso 1 1 d . . . H5A H 0.292(3) 0.511(3) 0.680(2) 0.006(6) Uiso 1 1 d . . . H4B H 0.477(3) 0.655(3) 0.812(2) 0.017(6) Uiso 1 1 d . . . H5B H 0.202(3) 0.640(4) 0.601(2) 0.028(7) Uiso 1 1 d . . . H1 H 0.610(3) 1.108(4) 0.811(2) 0.028(7) Uiso 1 1 d . . . Cu Cu 0.39392(2) 0.99873(3) 0.66025(2) 0.00915(10) 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 N 0.0091(7) 0.0097(7) 0.0068(7) 0.0002(6) 0.0024(6) 0.0002(6) O4 0.0230(8) 0.0119(7) 0.0125(7) -0.0029(5) 0.0074(7) 0.0008(6) O3 0.0187(7) 0.0115(7) 0.0127(7) -0.0009(5) 0.0084(6) 0.0027(6) O2 0.0189(7) 0.0098(6) 0.0139(7) -0.0015(5) 0.0109(6) 0.0001(6) C7 0.0108(9) 0.0157(9) 0.0142(10) 0.0023(8) 0.0079(8) 0.0026(7) C8 0.0187(10) 0.0126(10) 0.0118(9) 0.0021(7) 0.0047(8) 0.0050(8) O5 0.0356(10) 0.0217(8) 0.0246(9) 0.0051(7) 0.0211(8) 0.0136(7) C5 0.0142(9) 0.0121(9) 0.0110(9) -0.0032(8) 0.0036(8) -0.0042(8) C6 0.0131(9) 0.0122(9) 0.0099(9) 0.0021(7) 0.0020(7) 0.0017(7) C4 0.0127(9) 0.0103(8) 0.0109(9) 0.0017(7) 0.0038(7) 0.0009(7) C2 0.0137(9) 0.0116(9) 0.0104(9) 0.0013(7) 0.0035(7) -0.0002(7) O1 0.0152(7) 0.0126(7) 0.0093(7) -0.0005(5) 0.0059(6) -0.0038(5) C1 0.0108(9) 0.0119(9) 0.0078(9) 0.0026(7) 0.0038(7) 0.0006(7) C3 0.0127(9) 0.0118(9) 0.0124(9) 0.0009(7) 0.0039(8) -0.0023(7) O1W 0.0229(8) 0.0112(7) 0.0154(7) 0.0025(6) 0.0115(6) -0.0011(6) Cu 0.01273(15) 0.00754(14) 0.00875(15) -0.00005(8) 0.00567(10) -0.00003(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 N C7 1.484(3) . ? N C5 1.487(2) . ? N C4 1.507(2) . ? N Cu 2.0043(16) . ? O4 C6 1.240(2) . ? O3 C8 1.283(3) . ? O3 Cu 1.9337(14) . ? O2 C6 1.296(2) . ? O2 Cu 1.9479(14) . ? C7 C8 1.523(3) . ? C8 O5 1.231(3) . ? C5 C6 1.525(3) . ? C4 C2 1.502(3) . ? C2 C1 1.398(3) . ? C2 C3 1.399(3) . ? O1 C1 1.381(3) . ? O1 Cu 2.3592(17) . ? C1 C3 1.389(3) 3_677 ? C3 C1 1.389(3) 3_677 ? O1W Cu 1.9585(14) . ? 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 C7 N C5 114.12(16) . . ? C7 N C4 110.72(15) . . ? C5 N C4 108.51(15) . . ? C7 N Cu 104.44(12) . . ? C5 N Cu 106.12(12) . . ? C4 N Cu 112.89(12) . . ? C8 O3 Cu 112.94(13) . . ? C6 O2 Cu 113.34(12) . . ? N C7 C8 111.41(16) . . ? O5 C8 O3 126.0(2) . . ? O5 C8 C7 116.41(18) . . ? O3 C8 C7 117.52(17) . . ? N C5 C6 111.60(16) . . ? O4 C6 O2 124.30(19) . . ? O4 C6 C5 118.43(18) . . ? O2 C6 C5 117.26(17) . . ? C2 C4 N 112.35(16) . . ? C1 C2 C3 119.20(18) . . ? C1 C2 C4 120.13(18) . . ? C3 C2 C4 120.66(17) . . ? C1 O1 Cu 108.59(13) . . ? O1 C1 C3 122.74(17) . 3_677 ? O1 C1 C2 117.22(17) . . ? C3 C1 C2 120.02(19) 3_677 . ? C1 C3 C2 120.78(18) 3_677 . ? O3 Cu O2 162.38(7) . . ? O3 Cu O1W 94.41(6) . . ? O2 Cu O1W 92.89(7) . . ? O3 Cu N 86.89(7) . . ? O2 Cu N 85.64(7) . . ? O1W Cu N 178.48(6) . . ? O3 Cu O1 90.97(6) . . ? O2 Cu O1 104.98(6) . . ? O1W Cu O1 90.59(6) . . ? N Cu O1 90.16(6) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 31.26 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.819 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.101 # Attachment 'Cu4_complex.cif' data_Cu4 _database_code_depnum_ccdc_archive 'CCDC 680994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H76 Cu N6 O16' _chemical_formula_weight 1032.68 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9944(7) _cell_length_b 10.4356(6) _cell_length_c 13.1263(10) _cell_angle_alpha 80.650(5) _cell_angle_beta 87.789(6) _cell_angle_gamma 85.646(5) _cell_volume 1346.47(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.673 _exptl_crystal_size_mid 0.326 _exptl_crystal_size_min 0.204 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 551 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.719 _exptl_absorpt_correction_T_max 0.838 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 19981 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 30.11 _reflns_number_total 6863 _reflns_number_gt 6083 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0591P)^2^+0.4256P] 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 6863 _refine_ls_number_parameters 423 _refine_ls_number_restraints 194 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.118 _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 Cu Cu 0.0000 0.5000 0.5000 0.01188(7) Uani 1 2 d S . . O1 O 0.12268(12) 0.90975(9) 0.60314(7) 0.0202(2) Uani 1 1 d . . . O7 O 0.19476(13) 0.52701(10) 1.02849(8) 0.0253(2) Uani 1 1 d . . . O4 O -0.17558(11) 0.84825(9) 0.40896(8) 0.0199(2) Uani 1 1 d . . . O5 O -0.27400(11) 0.39262(10) 0.74124(7) 0.0204(2) Uani 1 1 d . . . O6 O 0.21359(15) 0.71912(11) 1.07790(8) 0.0307(3) Uani 1 1 d . . . O2 O -0.06912(10) 0.65375(8) 0.40879(7) 0.0155(2) Uani 1 1 d . . . O3 O -0.21961(11) 0.45428(9) 0.57583(7) 0.0174(2) Uani 1 1 d . . . N02 N 0.40049(14) 0.78848(12) 0.34072(10) 0.0225(3) Uani 1 1 d DU . . C18 C 0.3034(3) 0.8698(3) 0.3902(2) 0.0295(7) Uani 0.556(3) 1 d PDU A -1 H18A H 0.3470 0.9438 0.4059 0.035 Uiso 0.556(3) 1 calc PR A -1 H18B H 0.2734 0.8205 0.4551 0.035 Uiso 0.556(3) 1 calc PR A -1 C19 C 0.1810(4) 0.9195(5) 0.3254(4) 0.0273(9) Uani 0.556(3) 1 d PDU A -1 H19A H 0.1212 0.9727 0.3628 0.041 Uiso 0.556(3) 1 calc PR A -1 H19B H 0.1355 0.8469 0.3111 0.041 Uiso 0.556(3) 1 calc PR A -1 H19C H 0.2094 0.9701 0.2617 0.041 Uiso 0.556(3) 1 calc PR A -1 C20 C 0.5075(3) 0.7212(3) 0.4120(2) 0.0260(6) Uani 0.556(3) 1 d PDU A -1 H20A H 0.4653 0.6848 0.4769 0.031 Uiso 0.556(3) 1 calc PR A -1 H20B H 0.5666 0.7854 0.4263 0.031 Uiso 0.556(3) 1 calc PR A -1 C21 C 0.5920(11) 0.6124(8) 0.3692(6) 0.0379(19) Uani 0.556(3) 1 d PDU A -1 H21A H 0.6584 0.5744 0.4183 0.057 Uiso 0.556(3) 1 calc PR A -1 H21B H 0.6357 0.6477 0.3056 0.057 Uiso 0.556(3) 1 calc PR A -1 H21C H 0.5349 0.5468 0.3570 0.057 Uiso 0.556(3) 1 calc PR A -1 C22 C 0.4545(3) 0.8467(3) 0.2354(2) 0.0242(6) Uani 0.556(3) 1 d PDU A -1 H22A H 0.3803 0.8736 0.1893 0.029 Uiso 0.556(3) 1 calc PR A -1 H22B H 0.5116 0.7812 0.2069 0.029 Uiso 0.556(3) 1 calc PR A -1 C23 C 0.5341(4) 0.9630(3) 0.2416(3) 0.0365(8) Uani 0.556(3) 1 d PDU A -1 H23A H 0.5671 0.9978 0.1739 0.055 Uiso 0.556(3) 1 calc PR A -1 H23B H 0.6085 0.9363 0.2862 0.055 Uiso 0.556(3) 1 calc PR A -1 H23C H 0.4773 1.0286 0.2687 0.055 Uiso 0.556(3) 1 calc PR A -1 C18' C 0.3326(5) 0.9070(4) 0.2779(4) 0.0416(11) Uani 0.444(3) 1 d PDU A -2 H18C H 0.3395 0.8976 0.2055 0.050 Uiso 0.444(3) 1 calc PR A -2 H18D H 0.3793 0.9827 0.2860 0.050 Uiso 0.444(3) 1 calc PR A -2 C19' C 0.1856(8) 0.9299(14) 0.3082(11) 0.099(4) Uani 0.444(3) 1 d PDU A -2 H19D H 0.1479 1.0071 0.2661 0.148 Uiso 0.444(3) 1 calc PR A -2 H19E H 0.1780 0.9403 0.3795 0.148 Uiso 0.444(3) 1 calc PR A -2 H19F H 0.1380 0.8566 0.2980 0.148 Uiso 0.444(3) 1 calc PR A -2 C20' C 0.5381(4) 0.7586(4) 0.3079(3) 0.0317(9) Uani 0.444(3) 1 d PDU A -2 H20C H 0.5934 0.8278 0.3180 0.038 Uiso 0.444(3) 1 calc PR A -2 H20D H 0.5419 0.7513 0.2351 0.038 Uiso 0.444(3) 1 calc PR A -2 C21' C 0.5901(16) 0.6310(10) 0.3713(11) 0.058(3) Uani 0.444(3) 1 d PDU A -2 H21D H 0.6812 0.6102 0.3503 0.087 Uiso 0.444(3) 1 calc PR A -2 H21E H 0.5354 0.5629 0.3605 0.087 Uiso 0.444(3) 1 calc PR A -2 H21F H 0.5867 0.6392 0.4431 0.087 Uiso 0.444(3) 1 calc PR A -2 C22' C 0.3918(5) 0.8107(4) 0.4554(3) 0.0370(10) Uani 0.444(3) 1 d PDU A -2 H22C H 0.2979 0.8225 0.4756 0.044 Uiso 0.444(3) 1 calc PR A -2 H22D H 0.4294 0.7327 0.4981 0.044 Uiso 0.444(3) 1 calc PR A -2 C23' C 0.4630(5) 0.9262(4) 0.4784(3) 0.0388(11) Uani 0.444(3) 1 d PDU A -2 H23D H 0.4518 0.9320 0.5505 0.058 Uiso 0.444(3) 1 calc PR A -2 H23E H 0.4252 1.0047 0.4382 0.058 Uiso 0.444(3) 1 calc PR A -2 H23F H 0.5568 0.9146 0.4611 0.058 Uiso 0.444(3) 1 calc PR A -2 O8 O 0.67146(18) 0.67837(15) 0.06796(13) 0.0493(4) Uani 1 1 d D . . N N -0.02794(12) 0.60860(10) 0.61461(8) 0.0123(2) Uani 1 1 d . . . C6 C 0.12503(14) 0.71503(11) 0.72344(9) 0.0139(2) Uani 1 1 d . . . C1 C 0.13261(15) 0.85092(12) 0.70248(10) 0.0163(3) Uani 1 1 d . . . C4 C 0.16494(16) 0.71988(12) 0.90430(10) 0.0179(3) Uani 1 1 d . . . C5 C 0.14245(15) 0.65197(12) 0.82431(10) 0.0153(3) Uani 1 1 d . . . C7 C 0.19153(16) 0.64570(13) 1.00859(10) 0.0194(3) Uani 1 1 d . . . C11 C -0.09467(15) 0.53121(12) 0.70385(9) 0.0148(3) Uani 1 1 d . . . C10 C -0.11894(14) 0.74579(11) 0.45422(10) 0.0142(2) Uani 1 1 d . . . C9 C -0.11370(16) 0.72647(12) 0.57181(10) 0.0159(3) Uani 1 1 d . . . C3 C 0.16819(18) 0.85526(13) 0.88242(11) 0.0229(3) Uani 1 1 d . . . C8 C 0.11072(14) 0.63773(12) 0.63744(10) 0.0139(2) Uani 1 1 d . . . C2 C 0.15131(18) 0.92036(13) 0.78286(11) 0.0230(3) Uani 1 1 d . . . C13 C 0.5081(2) 0.5852(2) 0.85875(15) 0.0400(4) Uani 1 1 d . . . H13A H 0.4426 0.5258 0.8493 0.060 Uiso 1 1 calc R . . H13B H 0.4746 0.6378 0.9090 0.060 Uiso 1 1 calc R . . H13C H 0.5897 0.5369 0.8824 0.060 Uiso 1 1 calc R . . C16 C 0.7521(2) 0.78767(18) 0.05067(17) 0.0433(5) Uani 1 1 d . . . H16 H 0.7010 0.8609 0.0756 0.052 Uiso 1 1 calc R . . C12 C -0.20448(14) 0.45508(12) 0.66925(9) 0.0146(2) Uani 1 1 d . . . N01 N 0.5570(3) 0.7315(3) 0.68521(19) 0.0751(7) Uani 1 1 d . . . C14 C 0.5344(2) 0.6682(2) 0.76137(17) 0.0440(5) Uani 1 1 d . . . C15 C 0.7825(3) 0.8269(3) -0.0633(2) 0.0639(7) Uani 1 1 d . . . H15A H 0.8326 0.7564 -0.0893 0.096 Uiso 1 1 calc R . . H15B H 0.8342 0.9020 -0.0736 0.096 Uiso 1 1 calc R . . H15C H 0.6999 0.8473 -0.0994 0.096 Uiso 1 1 calc R . . C17 C 0.8783(3) 0.7578(2) 0.11051(17) 0.0474(5) Uani 1 1 d . . . H17A H 0.8560 0.7393 0.1829 0.071 Uiso 1 1 calc R . . H17B H 0.9321 0.8315 0.0975 0.071 Uiso 1 1 calc R . . H17C H 0.9278 0.6836 0.0895 0.071 Uiso 1 1 calc R . . H8B H 0.1438(19) 0.6822(17) 0.5757(14) 0.019(4) Uiso 1 1 d . . . H8A H 0.1609(18) 0.5566(17) 0.6534(13) 0.018(4) Uiso 1 1 d . . . H5 H 0.1407(18) 0.5583(17) 0.8403(14) 0.018(4) Uiso 1 1 d . . . H2 H 0.150(2) 1.0098(19) 0.7700(14) 0.023(5) Uiso 1 1 d . . . H9B H -0.0807(18) 0.8042(16) 0.5915(13) 0.015(4) Uiso 1 1 d . . . H3 H 0.185(2) 0.905(2) 0.9345(17) 0.037(6) Uiso 1 1 d . . . H11B H -0.0321(18) 0.4686(17) 0.7398(13) 0.016(4) Uiso 1 1 d . . . H11A H -0.1333(19) 0.5826(18) 0.7540(14) 0.021(4) Uiso 1 1 d . . . H1 H 0.139(2) 0.987(2) 0.5987(17) 0.036(6) Uiso 1 1 d . . . H9A H -0.202(2) 0.7174(18) 0.5966(15) 0.024(5) Uiso 1 1 d . . . H02 H 0.357(2) 0.724(2) 0.3306(16) 0.033(5) Uiso 1 1 d . . . H2' H 0.227(3) 0.673(3) 1.129(2) 0.058(8) Uiso 1 1 d . . . H8 H 0.712(3) 0.614(2) 0.039(2) 0.064(8) 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 Cu 0.01878(14) 0.00790(10) 0.00914(10) -0.00187(7) -0.00198(8) -0.00015(8) O1 0.0353(7) 0.0117(4) 0.0137(4) -0.0003(3) -0.0036(4) -0.0051(4) O7 0.0397(7) 0.0181(4) 0.0177(5) 0.0004(4) -0.0059(4) -0.0040(4) O4 0.0245(6) 0.0101(4) 0.0244(5) 0.0005(3) -0.0067(4) -0.0002(4) O5 0.0215(6) 0.0263(5) 0.0138(4) -0.0010(4) -0.0006(4) -0.0093(4) O6 0.0572(9) 0.0220(5) 0.0142(5) -0.0020(4) -0.0100(5) -0.0075(5) O2 0.0219(6) 0.0114(4) 0.0128(4) -0.0007(3) -0.0020(4) -0.0001(4) O3 0.0198(6) 0.0210(4) 0.0125(4) -0.0040(3) -0.0016(4) -0.0045(4) N02 0.0180(7) 0.0215(6) 0.0285(6) -0.0037(5) -0.0024(5) -0.0046(5) C18 0.0275(17) 0.0264(13) 0.0363(15) -0.0119(11) 0.0105(12) -0.0045(12) C19 0.021(2) 0.0245(16) 0.0369(17) -0.0094(13) 0.0047(14) 0.0036(16) C20 0.0261(17) 0.0277(13) 0.0249(12) -0.0025(10) -0.0090(11) -0.0065(11) C21 0.028(4) 0.037(3) 0.047(3) -0.009(2) -0.009(2) 0.017(3) C22 0.0254(16) 0.0236(12) 0.0231(12) -0.0026(9) 0.0031(10) -0.0030(11) C23 0.042(2) 0.0306(15) 0.0374(16) -0.0030(12) 0.0061(14) -0.0174(14) C18' 0.048(3) 0.0284(18) 0.050(2) -0.0110(17) -0.024(2) 0.0074(18) C19' 0.052(6) 0.096(8) 0.150(10) -0.039(7) -0.025(6) 0.035(5) C20' 0.021(2) 0.0349(18) 0.043(2) -0.0165(16) 0.0009(15) -0.0009(15) C21' 0.035(6) 0.032(3) 0.112(7) -0.017(3) -0.037(5) 0.001(3) C22' 0.048(3) 0.0332(19) 0.0333(19) -0.0121(15) 0.0122(18) -0.0177(18) C23' 0.058(3) 0.0338(19) 0.0301(19) -0.0147(15) 0.0027(19) -0.0194(19) O8 0.0518(10) 0.0399(8) 0.0574(9) -0.0129(7) 0.0114(8) -0.0069(7) N 0.0161(6) 0.0098(4) 0.0112(4) -0.0019(3) -0.0014(4) -0.0007(4) C6 0.0174(7) 0.0113(5) 0.0138(5) -0.0031(4) -0.0015(5) -0.0024(5) C1 0.0229(8) 0.0122(5) 0.0139(5) -0.0015(4) -0.0014(5) -0.0030(5) C4 0.0254(8) 0.0154(5) 0.0134(5) -0.0020(4) -0.0028(5) -0.0032(5) C5 0.0193(7) 0.0119(5) 0.0149(5) -0.0017(4) -0.0018(5) -0.0028(5) C7 0.0246(8) 0.0194(6) 0.0146(5) -0.0020(5) -0.0031(5) -0.0042(5) C11 0.0187(7) 0.0156(5) 0.0106(5) -0.0029(4) -0.0001(5) -0.0041(5) C10 0.0152(7) 0.0103(5) 0.0173(5) -0.0008(4) -0.0024(5) -0.0041(5) C9 0.0200(8) 0.0115(5) 0.0167(5) -0.0043(4) -0.0031(5) 0.0023(5) C3 0.0393(10) 0.0155(6) 0.0155(6) -0.0050(5) -0.0058(6) -0.0049(6) C8 0.0179(7) 0.0111(5) 0.0134(5) -0.0037(4) -0.0006(5) -0.0021(5) C2 0.0404(10) 0.0117(5) 0.0178(6) -0.0029(5) -0.0049(6) -0.0048(6) C13 0.0302(11) 0.0517(11) 0.0369(9) -0.0072(8) 0.0017(8) 0.0037(9) C16 0.0519(14) 0.0280(8) 0.0497(11) -0.0078(8) 0.0087(10) -0.0032(8) C12 0.0154(7) 0.0148(5) 0.0140(5) -0.0030(4) -0.0012(5) -0.0006(5) N01 0.0751(18) 0.0818(17) 0.0607(14) 0.0033(12) 0.0235(12) 0.0003(14) C14 0.0332(12) 0.0537(12) 0.0450(11) -0.0118(9) 0.0068(9) 0.0010(9) C15 0.075(2) 0.0602(15) 0.0515(13) 0.0116(11) -0.0087(13) -0.0143(14) C17 0.0574(15) 0.0375(10) 0.0474(11) -0.0080(8) 0.0062(10) -0.0049(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 Cu O2 1.9382(9) . ? Cu O2 1.9382(9) 2_566 ? Cu N 2.0246(10) . ? Cu N 2.0246(10) 2_566 ? Cu O3 2.4232(11) 2_566 ? Cu O3 2.4232(11) . ? O1 C1 1.3519(15) . ? O7 C7 1.2218(17) . ? O4 C10 1.2427(15) . ? O5 C12 1.2723(18) . ? O6 C7 1.3157(16) . ? O2 C10 1.2715(15) . ? O3 C12 1.2428(15) . ? N02 C18 1.445(3) . ? N02 C20' 1.452(4) . ? N02 C18' 1.502(4) . ? N02 C20 1.504(3) . ? N02 C22 1.514(3) . ? N02 C22' 1.558(4) . ? C18 C19 1.526(5) . ? C20 C21 1.530(6) . ? C22 C23 1.515(4) . ? C18' C19' 1.518(7) . ? C20' C21' 1.518(7) . ? C22' C23' 1.521(5) . ? O8 C16 1.429(3) . ? N C11 1.4775(17) . ? N C9 1.4887(15) . ? N C8 1.4928(18) . ? C6 C5 1.3906(17) . ? C6 C1 1.4071(17) . ? C6 C8 1.5071(16) . ? C1 C2 1.3992(17) . ? C4 C5 1.3926(17) . ? C4 C3 1.3978(18) . ? C4 C7 1.4821(18) . ? C11 C12 1.5264(19) . ? C10 C9 1.5262(18) . ? C3 C2 1.3817(19) . ? C13 C14 1.450(3) . ? C16 C17 1.498(3) . ? C16 C15 1.511(3) . ? N01 C14 1.130(3) . ? 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 Cu O2 180.00(5) . 2_566 ? O2 Cu N 86.18(4) . . ? O2 Cu N 93.82(4) 2_566 . ? O2 Cu N 93.82(4) . 2_566 ? O2 Cu N 86.18(4) 2_566 2_566 ? N Cu N 180.00(3) . 2_566 ? O2 Cu O3 86.87(4) . 2_566 ? O2 Cu O3 93.13(4) 2_566 2_566 ? N Cu O3 105.60(4) . 2_566 ? N Cu O3 74.40(4) 2_566 2_566 ? O2 Cu O3 93.13(4) . . ? O2 Cu O3 86.87(4) 2_566 . ? N Cu O3 74.40(4) . . ? N Cu O3 105.60(4) 2_566 . ? O3 Cu O3 180.0 2_566 . ? C10 O2 Cu 114.86(8) . . ? C12 O3 Cu 103.16(9) . . ? C18 N02 C20' 149.6(2) . . ? C18 N02 C18' 60.5(2) . . ? C20' N02 C18' 114.2(3) . . ? C18 N02 C20 113.27(19) . . ? C20' N02 C20 56.0(2) . . ? C18' N02 C20 152.6(2) . . ? C18 N02 C22 116.55(19) . . ? C20' N02 C22 58.6(2) . . ? C18' N02 C22 58.0(2) . . ? C20 N02 C22 113.54(19) . . ? C18 N02 C22' 51.2(2) . . ? C20' N02 C22' 111.4(3) . . ? C18' N02 C22' 106.9(3) . . ? C20 N02 C22' 62.0(2) . . ? C22 N02 C22' 141.6(2) . . ? N02 C18 C19 114.0(3) . . ? N02 C20 C21 114.0(4) . . ? N02 C22 C23 111.3(2) . . ? N02 C18' C19' 113.2(6) . . ? N02 C20' C21' 108.7(7) . . ? C23' C22' N02 115.6(3) . . ? C11 N C9 111.49(11) . . ? C11 N C8 112.55(10) . . ? C9 N C8 113.34(10) . . ? C11 N Cu 108.72(7) . . ? C9 N Cu 106.22(7) . . ? C8 N Cu 103.94(7) . . ? C5 C6 C1 118.47(11) . . ? C5 C6 C8 120.38(11) . . ? C1 C6 C8 120.92(11) . . ? O1 C1 C2 122.20(11) . . ? O1 C1 C6 117.69(11) . . ? C2 C1 C6 120.11(11) . . ? C5 C4 C3 118.87(12) . . ? C5 C4 C7 118.91(12) . . ? C3 C4 C7 122.15(12) . . ? C6 C5 C4 121.77(11) . . ? O7 C7 O6 122.78(12) . . ? O7 C7 C4 123.30(12) . . ? O6 C7 C4 113.91(12) . . ? N C11 C12 111.31(10) . . ? O4 C10 O2 123.94(12) . . ? O4 C10 C9 118.21(11) . . ? O2 C10 C9 117.80(10) . . ? N C9 C10 112.44(10) . . ? C2 C3 C4 120.55(12) . . ? N C8 C6 117.16(11) . . ? C3 C2 C1 120.17(12) . . ? O8 C16 C17 110.34(17) . . ? O8 C16 C15 110.64(19) . . ? C17 C16 C15 111.3(2) . . ? O3 C12 O5 124.01(13) . . ? O3 C12 C11 120.15(12) . . ? O5 C12 C11 115.82(11) . . ? N01 C14 C13 178.7(3) . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.866 _refine_diff_density_max 0.587 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.058 # Attachment 'Cu5_complex.cif' data_cu5 _database_code_depnum_ccdc_archive 'CCDC 680995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H58 Cu N6 O14' _chemical_formula_weight 910.58 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1979(8) _cell_length_b 18.3240(12) _cell_length_c 11.8085(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.975(7) _cell_angle_gamma 90.00 _cell_volume 2213.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.407 _exptl_crystal_size_mid 0.268 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 950 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 32545 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 31.06 _reflns_number_total 6440 _reflns_number_gt 4530 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0730P)^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 6440 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 N3 N 0.47731(18) 0.03166(11) -0.25912(18) 0.0367(4) Uani 1 1 d . . . C19 C 0.52018(19) 0.05755(11) -0.1635(2) 0.0277(4) Uani 1 1 d . . . C20 C 0.5775(2) 0.08881(14) -0.0379(2) 0.0407(6) Uani 1 1 d . . . Cu Cu 0.0000 0.0000 0.0000 0.01141(9) Uani 1 2 d S . . O5 O 0.23005(13) -0.14377(6) 0.27716(11) 0.0199(3) Uani 1 1 d . . . O1 O 0.16159(13) 0.23243(6) 0.22987(11) 0.0213(3) Uani 1 1 d . . . H1 H 0.2010 0.2714 0.2453 0.032 Uiso 1 1 calc R . . O4 O 0.31077(12) 0.09840(7) 0.00481(12) 0.0198(3) Uani 1 1 d . . . O6 O 0.24815(13) 0.13724(7) 0.76980(11) 0.0204(3) Uani 1 1 d . . . H02 H 0.2460 0.1157 0.8298 0.031 Uiso 1 1 calc R . . O3 O 0.16353(11) -0.09189(6) 0.09058(11) 0.0163(3) Uani 1 1 d . . . O2 O 0.11143(11) 0.05213(6) -0.05969(11) 0.0167(3) Uani 1 1 d . . . O7 O 0.12962(13) 0.04063(7) 0.66566(12) 0.0230(3) Uani 1 1 d . . . N2 N 0.30297(14) -0.16001(8) 0.52020(14) 0.0178(3) Uani 1 1 d . . . N N 0.11494(12) 0.03960(7) 0.17141(12) 0.0103(3) Uani 1 1 d . . . C7 C 0.18354(17) 0.09845(9) 0.66710(16) 0.0161(3) Uani 1 1 d . . . C3 C 0.24729(17) 0.20067(9) 0.55985(16) 0.0167(3) Uani 1 1 d . . . H3 H 0.2947 0.2224 0.6362 0.020 Uiso 1 1 calc R . . C16 C 0.2592(2) -0.10233(10) 0.58595(18) 0.0224(4) Uani 1 1 d . . . H16A H 0.1660 -0.0946 0.5405 0.027 Uiso 1 1 calc R . . H16B H 0.3030 -0.0569 0.5845 0.027 Uiso 1 1 calc R . . C6 C 0.10983(15) 0.13298(8) 0.32980(15) 0.0125(3) Uani 1 1 d . . . C1 C 0.17094(17) 0.20083(9) 0.33716(16) 0.0156(3) Uani 1 1 d . . . C11 C 0.14983(16) -0.02328(9) 0.25784(15) 0.0120(3) Uani 1 1 d . . . H11A H 0.0770 -0.0343 0.2795 0.014 Uiso 1 1 calc R . . H11B H 0.2241 -0.0102 0.3333 0.014 Uiso 1 1 calc R . . C4 C 0.18331(16) 0.13436(9) 0.55437(15) 0.0145(3) Uani 1 1 d . . . C2 C 0.24045(17) 0.23404(9) 0.45236(17) 0.0177(4) Uani 1 1 d . . . H2 H 0.2820 0.2785 0.4565 0.021 Uiso 1 1 calc R . . C18 C 0.24577(18) -0.23418(10) 0.51973(19) 0.0239(4) Uani 1 1 d . . . H18A H 0.2779 -0.2525 0.6040 0.029 Uiso 1 1 calc R . . H18B H 0.2742 -0.2674 0.4717 0.029 Uiso 1 1 calc R . . C13 C 0.50798(18) -0.09883(11) 0.53210(19) 0.0243(4) Uani 1 1 d . . . H13A H 0.6011 -0.1040 0.5625 0.037 Uiso 1 1 calc R . . H13B H 0.4875 -0.0562 0.5681 0.037 Uiso 1 1 calc R . . H13C H 0.4716 -0.0939 0.4435 0.037 Uiso 1 1 calc R . . C12 C 0.18368(16) -0.09123(8) 0.20137(16) 0.0132(3) Uani 1 1 d . . . C5 C 0.11512(16) 0.10151(8) 0.43876(15) 0.0138(3) Uani 1 1 d . . . H5 H 0.0723 0.0575 0.4348 0.017 Uiso 1 1 calc R . . C8 C 0.03740(16) 0.09589(8) 0.20561(15) 0.0125(3) Uani 1 1 d . . . H8A H -0.0401 0.0726 0.2064 0.015 Uiso 1 1 calc R . . H8B H 0.0086 0.1330 0.1416 0.015 Uiso 1 1 calc R . . C9 C 0.23204(15) 0.07054(9) 0.15873(15) 0.0131(3) Uani 1 1 d . . . H9A H 0.3076 0.0409 0.2064 0.016 Uiso 1 1 calc R . . H9B H 0.2478 0.1194 0.1934 0.016 Uiso 1 1 calc R . . C10 C 0.21763(16) 0.07386(8) 0.02554(16) 0.0134(3) Uani 1 1 d . . . C14 C 0.45081(18) -0.16564(10) 0.56703(18) 0.0238(4) Uani 1 1 d . . . H14A H 0.4886 -0.1709 0.6565 0.029 Uiso 1 1 calc R . . H14B H 0.4731 -0.2087 0.5320 0.029 Uiso 1 1 calc R . . C17 C 0.0974(2) -0.23207(12) 0.4651(2) 0.0371(5) Uani 1 1 d . . . H17A H 0.0642 -0.2803 0.4662 0.056 Uiso 1 1 calc R . . H17B H 0.0653 -0.2147 0.3813 0.056 Uiso 1 1 calc R . . H17C H 0.0690 -0.1999 0.5134 0.056 Uiso 1 1 calc R . . C15 C 0.2857(3) -0.12052(13) 0.7190(2) 0.0415(6) Uani 1 1 d . . . H15A H 0.2550 -0.0814 0.7543 0.062 Uiso 1 1 calc R . . H15B H 0.3779 -0.1269 0.7655 0.062 Uiso 1 1 calc R . . H15C H 0.2408 -0.1648 0.7214 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N3 0.0329(10) 0.0455(11) 0.0304(11) -0.0053(9) 0.0115(8) 0.0089(9) C19 0.0243(10) 0.0282(10) 0.0354(12) -0.0030(9) 0.0172(9) 0.0014(8) C20 0.0335(12) 0.0577(15) 0.0392(14) -0.0261(12) 0.0233(11) -0.0157(11) Cu 0.01357(14) 0.01299(14) 0.00780(15) -0.00069(10) 0.00446(11) -0.00205(10) O5 0.0306(7) 0.0131(6) 0.0144(6) 0.0013(5) 0.0075(5) 0.0073(5) O1 0.0371(7) 0.0131(6) 0.0135(6) -0.0006(5) 0.0102(6) -0.0091(5) O4 0.0199(6) 0.0253(7) 0.0179(7) 0.0018(5) 0.0116(5) -0.0046(5) O6 0.0319(7) 0.0201(6) 0.0110(6) -0.0017(5) 0.0105(5) -0.0033(5) O3 0.0222(6) 0.0160(6) 0.0117(6) -0.0008(4) 0.0079(5) 0.0028(5) O2 0.0176(6) 0.0224(6) 0.0099(6) 0.0001(5) 0.0052(5) -0.0047(5) O7 0.0331(7) 0.0218(7) 0.0188(7) -0.0009(5) 0.0153(6) -0.0070(6) N2 0.0221(8) 0.0150(7) 0.0178(8) 0.0007(6) 0.0098(6) 0.0022(6) N 0.0129(6) 0.0095(6) 0.0089(7) 0.0005(5) 0.0049(5) 0.0000(5) C7 0.0199(8) 0.0173(8) 0.0137(9) 0.0001(6) 0.0094(7) 0.0024(6) C3 0.0214(8) 0.0159(8) 0.0119(8) -0.0041(6) 0.0058(7) -0.0018(6) C16 0.0305(10) 0.0190(8) 0.0209(10) 0.0003(7) 0.0140(8) 0.0042(7) C6 0.0145(7) 0.0113(7) 0.0125(8) -0.0011(6) 0.0062(6) 0.0009(6) C1 0.0217(8) 0.0127(7) 0.0136(8) 0.0000(6) 0.0084(7) -0.0004(6) C11 0.0156(7) 0.0120(7) 0.0082(8) 0.0005(6) 0.0044(6) 0.0006(6) C4 0.0192(8) 0.0151(7) 0.0112(8) 0.0003(6) 0.0081(7) 0.0019(6) C2 0.0246(9) 0.0123(7) 0.0179(9) -0.0015(6) 0.0102(7) -0.0033(6) C18 0.0290(10) 0.0161(8) 0.0296(11) 0.0035(7) 0.0149(9) 0.0015(7) C13 0.0217(9) 0.0279(10) 0.0221(10) -0.0013(7) 0.0074(8) -0.0017(7) C12 0.0144(7) 0.0116(7) 0.0133(8) -0.0012(6) 0.0053(6) -0.0002(6) C5 0.0160(8) 0.0116(7) 0.0160(9) -0.0011(6) 0.0088(7) 0.0001(6) C8 0.0147(7) 0.0106(7) 0.0134(8) -0.0006(6) 0.0070(6) 0.0019(6) C9 0.0128(7) 0.0150(7) 0.0117(8) -0.0014(6) 0.0051(6) -0.0023(6) C10 0.0170(8) 0.0108(7) 0.0144(8) 0.0012(6) 0.0084(7) 0.0013(6) C14 0.0228(9) 0.0252(9) 0.0226(10) 0.0028(7) 0.0082(8) 0.0039(7) C17 0.0302(11) 0.0243(10) 0.0602(16) 0.0038(10) 0.0219(11) -0.0008(8) C15 0.0714(17) 0.0348(12) 0.0267(12) 0.0044(9) 0.0283(12) 0.0148(11) _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 N3 C19 1.136(3) . ? C19 C20 1.472(3) . ? Cu O2 1.9183(12) 3 ? Cu O2 1.9183(12) . ? Cu N 2.0402(13) 3 ? Cu N 2.0402(13) . ? Cu O3 2.3965(12) . ? Cu O3 2.3965(12) 3 ? O5 C12 1.2729(19) . ? O1 C1 1.358(2) . ? O4 C10 1.248(2) . ? O6 C7 1.336(2) . ? O3 C12 1.234(2) . ? O2 C10 1.270(2) . ? O7 C7 1.216(2) . ? N2 C18 1.501(2) . ? N2 C16 1.507(2) . ? N2 C14 1.521(2) . ? N C11 1.483(2) . ? N C9 1.491(2) . ? N C8 1.506(2) . ? C7 C4 1.484(2) . ? C3 C2 1.383(2) . ? C3 C4 1.398(2) . ? C16 C15 1.512(3) . ? C6 C5 1.389(2) . ? C6 C1 1.405(2) . ? C6 C8 1.518(2) . ? C1 C2 1.402(2) . ? C11 C12 1.531(2) . ? C4 C5 1.401(2) . ? C18 C17 1.519(3) . ? C13 C14 1.514(3) . ? C9 C10 1.516(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 N3 C19 C20 178.2(2) . . ? O2 Cu O2 180.00(8) 3 . ? O2 Cu N 86.87(5) 3 3 ? O2 Cu N 93.13(5) . 3 ? O2 Cu N 93.13(5) 3 . ? O2 Cu N 86.87(5) . . ? N Cu N 180.00(9) 3 . ? O2 Cu O3 88.82(5) 3 . ? O2 Cu O3 91.18(5) . . ? N Cu O3 104.63(5) 3 . ? N Cu O3 75.37(5) . . ? O2 Cu O3 91.18(5) 3 3 ? O2 Cu O3 88.82(5) . 3 ? N Cu O3 75.37(5) 3 3 ? N Cu O3 104.63(5) . 3 ? O3 Cu O3 180.00(4) . 3 ? C12 O3 Cu 104.11(10) . . ? C10 O2 Cu 113.84(11) . . ? C18 N2 C16 114.15(15) . . ? C18 N2 C14 109.83(13) . . ? C16 N2 C14 113.25(14) . . ? C11 N C9 111.58(12) . . ? C11 N C8 111.55(13) . . ? C9 N C8 113.16(12) . . ? C11 N Cu 106.88(9) . . ? C9 N Cu 105.15(10) . . ? C8 N Cu 108.04(9) . . ? O7 C7 O6 123.95(16) . . ? O7 C7 C4 123.63(16) . . ? O6 C7 C4 112.41(14) . . ? C2 C3 C4 120.35(16) . . ? N2 C16 C15 114.39(16) . . ? C5 C6 C1 118.28(15) . . ? C5 C6 C8 120.94(14) . . ? C1 C6 C8 120.77(15) . . ? O1 C1 C2 121.49(15) . . ? O1 C1 C6 117.95(15) . . ? C2 C1 C6 120.55(15) . . ? N C11 C12 112.02(13) . . ? C3 C4 C5 118.98(16) . . ? C3 C4 C7 121.97(15) . . ? C5 C4 C7 119.03(15) . . ? C3 C2 C1 120.05(15) . . ? N2 C18 C17 111.70(15) . . ? O3 C12 O5 125.78(15) . . ? O3 C12 C11 119.91(14) . . ? O5 C12 C11 114.30(14) . . ? C6 C5 C4 121.71(15) . . ? N C8 C6 115.21(13) . . ? N C9 C10 113.10(13) . . ? O4 C10 O2 123.06(16) . . ? O4 C10 C9 118.23(14) . . ? O2 C10 C9 118.71(14) . . ? C13 C14 N2 111.34(14) . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 31.06 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.907 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.076 # Attachment 'Cu6_complex.cif' data_Cu6 _database_code_depnum_ccdc_archive 'CCDC 680996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cu2 N2 Na4 O14' _chemical_formula_weight 681.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' Na Na 0.0362 0.0249 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2884(9) _cell_length_b 10.9093(9) _cell_length_c 11.6971(10) _cell_angle_alpha 107.320(8) _cell_angle_beta 93.564(7) _cell_angle_gamma 95.379(7) _cell_volume 1242.21(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.369 _exptl_crystal_size_min 0.166 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 1.854 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.444 _exptl_absorpt_correction_T_max 0.735 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 14948 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 31.10 _reflns_number_total 6468 _reflns_number_gt 5076 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1148P)^2^+0.8047P] 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 6468 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1819 _refine_ls_wR_factor_gt 0.1698 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.011 _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 O3 O 0.8635(3) 0.2109(2) 0.3224(2) 0.0128(5) Uani 1 1 d . . . C7 C 1.0566(4) 0.3358(3) 0.4415(3) 0.0109(7) Uani 1 1 d . . . C12 C 0.5780(4) 0.0767(3) 0.4505(3) 0.0101(7) Uani 1 1 d . . . C3 C 1.0884(3) 0.0742(3) 0.4525(3) 0.0087(6) Uani 1 1 d . . . C13 C 1.3925(3) -0.0817(3) 0.4290(3) 0.0098(6) Uani 1 1 d . . . C14 C 1.2753(4) -0.1668(3) 0.3578(3) 0.0112(7) Uani 1 1 d . . . C8 C 0.9083(4) 0.2991(3) 0.4199(3) 0.0114(7) Uani 1 1 d . . . C2 C 0.9065(4) -0.0916(3) 0.4233(3) 0.0112(7) Uani 1 1 d . . . C1 C 0.9937(4) -0.0187(3) 0.3767(3) 0.0097(6) Uani 1 1 d . . . O1 O 0.9928(3) -0.0365(2) 0.2548(2) 0.0107(5) Uani 1 1 d . . . O5 O 0.8389(3) 0.3590(2) 0.4958(2) 0.0142(5) Uani 1 1 d . . . O1W O 0.8627(3) 0.0858(2) 0.0694(2) 0.0140(5) Uani 1 1 d . . . O2W O 0.9920(3) 0.3650(2) 0.1732(2) 0.0156(5) Uani 1 1 d . . . C11 C 0.4728(4) -0.0029(3) 0.3812(3) 0.0115(7) Uani 1 1 d . . . C4 C 1.1867(4) 0.1515(3) 0.4032(3) 0.0100(6) Uani 1 1 d . . . O11 O 0.4390(3) -0.0091(2) 0.2629(2) 0.0118(5) Uani 1 1 d . . . O11W O 0.5226(3) 0.1734(3) -0.0116(2) 0.0220(6) Uani 1 1 d . . . O12W O 0.6287(3) -0.5323(4) -0.0161(3) 0.0417(9) Uani 1 1 d . . . Na2 Na 0.6073(3) 0.1671(3) 0.2055(2) 0.0573(7) Uani 1 1 d . . . Na3 Na 0.8180(3) -0.4503(3) 0.1816(3) 0.0620(7) Uani 1 1 d . . . Na1 Na 0.7801(3) -0.1741(3) 0.1387(3) 0.0705(8) Uani 1 1 d . . . Na4 Na 0.6020(3) 0.3930(3) 0.3843(3) 0.0688(8) Uani 1 1 d . . . H4B H 1.247(4) 0.201(4) 0.470(3) 0.000(8) Uiso 1 1 d . . . H7B H 1.074(4) 0.426(4) 0.435(4) 0.008(10) Uiso 1 1 d . . . H4A H 1.229(5) 0.092(5) 0.340(4) 0.021(12) Uiso 1 1 d . . . H14A H 1.226(5) -0.118(5) 0.320(4) 0.021(12) Uiso 1 1 d . . . H17B H 0.380(5) -0.477(6) 0.245(5) 0.043(16) Uiso 1 1 d . . . H12 H 0.618(4) 0.107(4) 0.421(4) 0.002(9) Uiso 1 1 d . . . H15A H 1.115(5) -0.353(5) 0.270(4) 0.024(12) Uiso 1 1 d . . . H7A H 1.083(4) 0.347(4) 0.525(4) 0.008(9) Uiso 1 1 d . . . H14B H 1.212(4) -0.202(4) 0.412(4) 0.015(11) Uiso 1 1 d . . . H5A H 1.305(4) 0.317(4) 0.340(4) 0.001(9) Uiso 1 1 d . . . H17A H 0.398(5) -0.341(5) 0.393(5) 0.030(14) Uiso 1 1 d . . . H1WA H 0.853(5) 0.131(5) 0.034(4) 0.018(12) Uiso 1 1 d . . . H5B H 1.224(4) 0.394(5) 0.317(4) 0.014(11) Uiso 1 1 d . . . H15B H 1.205(4) -0.443(4) 0.164(3) 0.000(8) Uiso 1 1 d . . . H2WA H 0.923(6) 0.418(6) 0.182(5) 0.040(15) Uiso 1 1 d . . . H2 H 0.857(5) -0.149(5) 0.375(5) 0.027(14) Uiso 1 1 d . . . H1WB H 0.854(5) 0.006(5) 0.015(5) 0.025(13) Uiso 1 1 d . . . H2WB H 0.998(5) 0.347(5) 0.101(5) 0.025(13) Uiso 1 1 d . . . Cu1 Cu 0.99501(4) 0.16136(4) 0.20940(3) 0.00946(13) Uani 1 1 d . . . O2 O 1.1497(3) 0.1488(2) 0.1164(2) 0.0135(5) Uani 1 1 d . . . N1 N 1.1272(3) 0.2467(3) 0.3520(2) 0.0091(5) Uani 1 1 d . . . Cu11 Cu 0.39061(4) -0.23433(4) 0.13171(4) 0.01027(14) Uani 1 1 d . . . O13 O 0.5548(3) -0.2620(2) 0.2107(2) 0.0130(5) Uani 1 1 d . . . O12 O 1.2098(3) -0.2332(2) 0.0690(2) 0.0127(5) Uani 1 1 d . . . N11 N 1.3056(3) -0.2851(3) 0.2626(3) 0.0096(6) Uani 1 1 d . . . O14 O 1.0079(3) -0.3274(3) 0.0721(2) 0.0150(5) Uani 1 1 d . . . O15 O 0.6286(3) 0.6380(2) 0.3371(2) 0.0150(5) Uani 1 1 d . . . O4 O 0.6748(3) -0.2854(3) -0.1156(2) 0.0222(6) Uani 1 1 d . . . C16 C 1.1245(4) -0.3029(3) 0.1089(3) 0.0122(7) Uani 1 1 d . . . C15 C 1.1797(4) -0.3592(3) 0.2043(3) 0.0132(7) Uani 1 1 d . . . C18 C 0.5380(4) -0.3249(3) 0.2872(3) 0.0119(7) Uani 1 1 d . . . C6 C 1.2385(4) 0.2431(3) 0.1682(3) 0.0125(7) Uani 1 1 d . . . C5 C 1.2323(4) 0.3127(3) 0.3012(3) 0.0110(7) Uani 1 1 d . . . C17 C 0.3965(4) -0.3601(3) 0.3095(3) 0.0123(7) 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 O3 0.0120(14) 0.0133(11) 0.0123(12) 0.0028(9) 0.0015(11) 0.0014(9) C7 0.0158(19) 0.0071(13) 0.0088(14) 0.0005(11) 0.0031(14) 0.0016(12) C12 0.0118(19) 0.0118(14) 0.0083(14) 0.0054(12) 0.0024(14) 0.0003(12) C3 0.0089(18) 0.0088(13) 0.0083(14) 0.0026(11) -0.0008(13) 0.0011(11) C13 0.0107(18) 0.0107(13) 0.0075(14) 0.0022(11) -0.0001(13) 0.0011(12) C14 0.0142(19) 0.0094(13) 0.0093(14) 0.0020(11) 0.0020(14) 0.0004(12) C8 0.0161(19) 0.0091(13) 0.0103(15) 0.0046(11) 0.0020(14) 0.0022(12) C2 0.016(2) 0.0077(14) 0.0082(15) 0.0005(11) -0.0002(15) 0.0015(12) C1 0.0111(18) 0.0102(13) 0.0070(14) 0.0016(11) -0.0011(13) 0.0016(11) O1 0.0137(14) 0.0108(10) 0.0066(11) 0.0024(8) -0.0001(10) -0.0012(9) O5 0.0136(14) 0.0132(11) 0.0165(12) 0.0035(9) 0.0074(11) 0.0040(9) O1W 0.0197(15) 0.0115(11) 0.0096(11) 0.0030(10) -0.0044(11) 0.0010(10) O2W 0.0197(16) 0.0153(12) 0.0129(13) 0.0058(10) -0.0003(11) 0.0041(10) C11 0.0138(19) 0.0115(14) 0.0096(15) 0.0033(12) 0.0023(14) 0.0021(12) C4 0.0104(18) 0.0084(13) 0.0105(15) 0.0026(11) -0.0020(14) -0.0002(11) O11 0.0140(14) 0.0152(11) 0.0064(11) 0.0046(9) -0.0004(10) -0.0008(9) O11W 0.0179(16) 0.0388(16) 0.0154(13) 0.0149(12) 0.0067(12) 0.0082(12) O12W 0.024(2) 0.057(2) 0.0247(17) -0.0182(16) -0.0026(15) 0.0114(16) Na2 0.0580(17) 0.0661(16) 0.0536(15) 0.0282(13) 0.0068(13) 0.0030(13) Na3 0.0643(19) 0.0545(15) 0.0699(18) 0.0201(14) 0.0127(15) 0.0120(13) Na1 0.0602(19) 0.093(2) 0.0506(16) 0.0151(15) 0.0061(14) -0.0088(16) Na4 0.075(2) 0.0578(16) 0.074(2) 0.0232(15) 0.0033(17) 0.0026(15) Cu1 0.0107(3) 0.0100(2) 0.0068(2) 0.00140(15) -0.00027(17) 0.00122(15) O2 0.0159(15) 0.0147(11) 0.0075(11) -0.0007(9) 0.0007(11) 0.0039(10) N1 0.0100(15) 0.0082(11) 0.0091(12) 0.0019(10) 0.0021(12) 0.0023(10) Cu11 0.0091(3) 0.0132(2) 0.0088(2) 0.00386(16) -0.00047(18) 0.00143(16) O13 0.0134(14) 0.0153(11) 0.0119(12) 0.0063(9) 0.0006(11) 0.0025(9) O12 0.0106(14) 0.0164(11) 0.0116(11) 0.0051(9) -0.0001(10) 0.0023(9) N11 0.0086(16) 0.0100(12) 0.0093(13) 0.0031(10) -0.0030(12) -0.0004(10) O14 0.0057(14) 0.0226(13) 0.0162(12) 0.0067(10) -0.0043(11) 0.0000(10) O15 0.0126(14) 0.0176(12) 0.0147(12) 0.0056(10) -0.0034(11) 0.0024(10) O4 0.0181(16) 0.0302(15) 0.0164(13) 0.0047(11) 0.0082(12) -0.0031(11) C16 0.016(2) 0.0118(14) 0.0081(14) 0.0012(11) -0.0003(14) 0.0032(12) C15 0.0109(19) 0.0135(15) 0.0137(16) 0.0041(12) -0.0044(14) -0.0029(12) C18 0.015(2) 0.0091(13) 0.0087(14) -0.0002(11) -0.0010(14) 0.0004(12) C6 0.0123(19) 0.0152(15) 0.0098(15) 0.0036(12) -0.0009(14) 0.0027(12) C5 0.010(2) 0.0108(15) 0.0123(15) 0.0044(12) 0.0008(15) -0.0023(12) C17 0.0100(19) 0.0123(14) 0.0151(16) 0.0063(12) -0.0051(14) 0.0016(12) _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 O3 C8 1.279(4) . ? O3 Cu1 1.950(2) . ? O3 Na2 2.823(4) . ? C7 N1 1.479(4) . ? C7 C8 1.527(5) . ? C12 C11 1.370(5) . ? C12 C13 1.407(4) 2_756 ? C3 C1 1.391(5) . ? C3 C2 1.405(4) 2_756 ? C3 C4 1.506(4) . ? C13 C11 1.395(4) 1_655 ? C13 C12 1.407(4) 2_756 ? C13 C14 1.488(5) . ? C14 N11 1.506(4) . ? C8 O5 1.244(4) . ? C2 C1 1.385(4) . ? C2 C3 1.405(4) 2_756 ? C1 O1 1.380(4) . ? O1 Cu1 2.370(2) . ? O1 Na1 2.586(4) . ? O5 Na4 2.801(4) . ? O1W Cu1 1.980(3) . ? O2W Cu1 2.385(2) . ? O2W Na3 2.802(4) 1_565 ? C11 O11 1.385(4) . ? C11 C13 1.395(4) 1_455 ? C4 N1 1.503(4) . ? O11 Na2 2.726(3) . ? O11W Cu11 1.952(2) 2_655 ? O11W Na2 2.656(4) . ? O12W Na3 2.798(5) . ? Na2 Na4 2.724(4) . ? Na2 Na1 4.160(4) . ? Na3 O15 2.790(4) 1_545 ? Na3 O2W 2.802(4) 1_545 ? Na3 O14 2.846(4) . ? Na3 Na1 3.252(4) . ? Na3 Na4 3.980(4) 1_545 ? Na1 O13 2.703(4) . ? Na1 O4 2.950(4) . ? Na1 O14 3.014(4) . ? Na4 O15 2.878(4) . ? Na4 Na4 3.878(6) 2_666 ? Na4 Na3 3.980(4) 1_565 ? Cu1 O2 1.976(2) . ? Cu1 N1 2.014(3) . ? O2 C6 1.283(4) . ? N1 C5 1.493(4) . ? Cu11 O11W 1.952(2) 2_655 ? Cu11 O12 1.960(3) 1_455 ? Cu11 O13 1.966(3) . ? Cu11 N11 1.999(3) 1_455 ? O13 C18 1.291(4) . ? O12 C16 1.305(4) . ? O12 Cu11 1.960(3) 1_655 ? N11 C15 1.470(5) . ? N11 C17 1.481(4) 1_655 ? N11 Cu11 1.999(3) 1_655 ? O14 C16 1.226(5) . ? O15 C18 1.232(4) 1_565 ? O15 Na3 2.790(4) 1_565 ? O4 C6 1.244(4) 2_755 ? C16 C15 1.528(5) . ? C18 O15 1.232(4) 1_545 ? C18 C17 1.529(5) . ? C6 O4 1.244(4) 2_755 ? C6 C5 1.523(5) . ? C17 N11 1.481(4) 1_455 ? 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 C8 O3 Cu1 113.6(2) . . ? C8 O3 Na2 127.4(2) . . ? Cu1 O3 Na2 112.22(12) . . ? N1 C7 C8 112.2(3) . . ? C11 C12 C13 121.3(3) . 2_756 ? C1 C3 C2 118.4(3) . 2_756 ? C1 C3 C4 121.2(3) . . ? C2 C3 C4 120.3(3) 2_756 . ? C11 C13 C12 118.4(3) 1_655 2_756 ? C11 C13 C14 122.0(3) 1_655 . ? C12 C13 C14 119.6(3) 2_756 . ? C13 C14 N11 114.7(3) . . ? O5 C8 O3 124.4(4) . . ? O5 C8 C7 118.2(3) . . ? O3 C8 C7 117.4(3) . . ? C1 C2 C3 121.1(3) . 2_756 ? O1 C1 C2 122.1(3) . . ? O1 C1 C3 117.4(3) . . ? C2 C1 C3 120.4(3) . . ? C1 O1 Cu1 112.02(18) . . ? C1 O1 Na1 111.3(2) . . ? Cu1 O1 Na1 104.73(12) . . ? C8 O5 Na4 110.7(2) . . ? Cu1 O2W Na3 138.59(13) . 1_565 ? C12 C11 O11 123.1(3) . . ? C12 C11 C13 120.4(3) . 1_455 ? O11 C11 C13 116.5(3) . 1_455 ? N1 C4 C3 113.4(3) . . ? C11 O11 Na2 108.3(2) . . ? Cu11 O11W Na2 132.15(16) 2_655 . ? O11W Na2 Na4 114.20(13) . . ? O11W Na2 O11 107.51(13) . . ? Na4 Na2 O11 104.95(12) . . ? O11W Na2 O3 130.71(12) . . ? Na4 Na2 O3 77.66(11) . . ? O11 Na2 O3 115.27(11) . . ? O11W Na2 Na1 104.12(11) . . ? Na4 Na2 Na1 139.98(12) . . ? O11 Na2 Na1 72.51(9) . . ? O3 Na2 Na1 68.61(9) . . ? O15 Na3 O12W 91.26(12) 1_545 . ? O15 Na3 O2W 132.02(13) 1_545 1_545 ? O12W Na3 O2W 111.25(14) . 1_545 ? O15 Na3 O14 133.96(13) 1_545 . ? O12W Na3 O14 96.68(13) . . ? O2W Na3 O14 86.48(11) 1_545 . ? O15 Na3 Na1 78.34(10) 1_545 . ? O12W Na3 Na1 80.09(12) . . ? O2W Na3 Na1 144.93(13) 1_545 . ? O14 Na3 Na1 58.78(9) . . ? O15 Na3 Na4 46.31(8) 1_545 1_545 ? O12W Na3 Na4 93.60(12) . 1_545 ? O2W Na3 Na4 89.00(10) 1_545 1_545 ? O14 Na3 Na4 169.69(13) . 1_545 ? Na1 Na3 Na4 124.32(11) . 1_545 ? O1 Na1 O13 132.85(13) . . ? O1 Na1 O4 136.30(13) . . ? O13 Na1 O4 90.76(12) . . ? O1 Na1 O14 71.24(11) . . ? O13 Na1 O14 125.05(14) . . ? O4 Na1 O14 86.61(11) . . ? O1 Na1 Na3 100.50(13) . . ? O13 Na1 Na3 71.87(10) . . ? O4 Na1 Na3 95.38(12) . . ? O14 Na1 Na3 53.86(9) . . ? O1 Na1 Na2 87.68(11) . . ? O13 Na1 Na2 83.08(10) . . ? O4 Na1 Na2 96.73(11) . . ? O14 Na1 Na2 151.73(11) . . ? Na3 Na1 Na2 152.25(10) . . ? Na2 Na4 O5 90.55(12) . . ? Na2 Na4 O15 121.30(13) . . ? O5 Na4 O15 109.44(12) . . ? Na2 Na4 Na4 147.08(16) . 2_666 ? O5 Na4 Na4 111.05(14) . 2_666 ? O15 Na4 Na4 75.76(10) . 2_666 ? Na2 Na4 Na3 84.74(10) . 1_565 ? O5 Na4 Na3 86.75(10) . 1_565 ? O15 Na4 Na3 44.51(8) . 1_565 ? Na4 Na4 Na3 119.75(12) 2_666 1_565 ? O3 Cu1 O2 167.18(11) . . ? O3 Cu1 O1W 93.60(11) . . ? O2 Cu1 O1W 96.31(11) . . ? O3 Cu1 N1 85.45(11) . . ? O2 Cu1 N1 84.27(11) . . ? O1W Cu1 N1 177.21(10) . . ? O3 Cu1 O1 88.70(9) . . ? O2 Cu1 O1 98.94(9) . . ? O1W Cu1 O1 92.64(10) . . ? N1 Cu1 O1 89.96(10) . . ? O3 Cu1 O2W 88.44(10) . . ? O2 Cu1 O2W 83.71(10) . . ? O1W Cu1 O2W 88.46(10) . . ? N1 Cu1 O2W 88.89(10) . . ? O1 Cu1 O2W 177.00(9) . . ? C6 O2 Cu1 110.1(2) . . ? C7 N1 C5 114.2(3) . . ? C7 N1 C4 111.5(2) . . ? C5 N1 C4 108.4(3) . . ? C7 N1 Cu1 105.9(2) . . ? C5 N1 Cu1 103.7(2) . . ? C4 N1 Cu1 112.9(2) . . ? O11W Cu11 O12 97.18(11) 2_655 1_455 ? O11W Cu11 O13 94.23(11) 2_655 . ? O12 Cu11 O13 167.71(10) 1_455 . ? O11W Cu11 N11 176.18(12) 2_655 1_455 ? O12 Cu11 N11 83.96(11) 1_455 1_455 ? O13 Cu11 N11 84.95(11) . 1_455 ? C18 O13 Cu11 114.0(2) . . ? C18 O13 Na1 129.4(2) . . ? Cu11 O13 Na1 116.60(12) . . ? C16 O12 Cu11 112.9(2) . 1_655 ? C15 N11 C17 114.5(3) . 1_655 ? C15 N11 C14 107.3(3) . . ? C17 N11 C14 112.9(3) 1_655 . ? C15 N11 Cu11 104.7(2) . 1_655 ? C17 N11 Cu11 106.9(2) 1_655 1_655 ? C14 N11 Cu11 110.17(18) . 1_655 ? C16 O14 Na3 123.4(2) . . ? C16 O14 Na1 131.1(2) . . ? Na3 O14 Na1 67.35(10) . . ? C18 O15 Na3 112.0(2) 1_565 1_565 ? C18 O15 Na4 122.0(2) 1_565 . ? Na3 O15 Na4 89.18(11) 1_565 . ? C6 O4 Na1 102.0(2) 2_755 . ? O14 C16 O12 124.1(3) . . ? O14 C16 C15 120.3(3) . . ? O12 C16 C15 115.6(3) . . ? N11 C15 C16 110.1(3) . . ? O15 C18 O13 123.4(3) 1_545 . ? O15 C18 C17 119.8(3) 1_545 . ? O13 C18 C17 116.8(3) . . ? O4 C6 O2 124.2(3) 2_755 . ? O4 C6 C5 118.0(3) 2_755 . ? O2 C6 C5 117.7(3) . . ? N1 C5 C6 111.3(3) . . ? N11 C17 C18 111.3(3) 1_455 . ? _diffrn_measured_fraction_theta_max 0.811 _diffrn_reflns_theta_full 31.10 _diffrn_measured_fraction_theta_full 0.811 _refine_diff_density_max 1.619 _refine_diff_density_min -1.831 _refine_diff_density_rms 0.163 # Attachment 'Cu7_complex.cif' data_Cu7 _database_code_depnum_ccdc_archive 'CCDC 680997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H68 Cu2 N2 O18 P2' _chemical_formula_weight 1438.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9672(7) _cell_length_b 12.2783(7) _cell_length_c 12.6196(7) _cell_angle_alpha 86.504(5) _cell_angle_beta 66.668(5) _cell_angle_gamma 70.169(5) _cell_volume 1595.89(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.336 _exptl_crystal_size_mid 0.278 _exptl_crystal_size_min 0.164 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 746 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.614 _exptl_absorpt_correction_T_max 0.783 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 30298 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 31.12 _reflns_number_total 8424 _reflns_number_gt 7616 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0379P)^2^+1.2840P] 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 8424 _refine_ls_number_parameters 473 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.97149(11) 0.97204(9) 0.10528(8) 0.0100(2) Uani 1 1 d . . . N N 1.25238(13) 1.07951(10) -0.09931(10) 0.0088(2) Uani 1 1 d . . . O5 O 1.46024(12) 0.87515(10) 0.01200(10) 0.0167(2) Uani 1 1 d . . . O3 O 1.24463(11) 0.93935(9) 0.06750(9) 0.0129(2) Uani 1 1 d . . . O2 O 1.02199(12) 1.21009(9) 0.06613(10) 0.0157(2) Uani 1 1 d . . . C12 C 1.36040(16) 0.92756(12) -0.00375(12) 0.0116(3) Uani 1 1 d . . . C10 C 1.24658(16) 1.18226(12) -0.03788(12) 0.0122(3) Uani 1 1 d . . . H10A H 1.2893 1.2280 -0.0942 0.015 Uiso 1 1 calc R . . H10B H 1.2929 1.1560 0.0121 0.015 Uiso 1 1 calc R . . C13 C 0.19694(15) 0.52315(12) 0.30046(12) 0.0116(3) Uani 1 1 d . . . C20 C 0.48031(17) 0.37177(13) 0.14295(13) 0.0146(3) Uani 1 1 d . . . H20 H 0.4137 0.4003 0.1173 0.018 Uiso 1 1 calc R . . C31 C 0.23303(16) 0.28171(12) 0.36538(12) 0.0115(3) Uani 1 1 d . . . C21 C 0.60827(17) 0.33465(14) 0.06400(13) 0.0166(3) Uani 1 1 d . . . H21 H 0.6276 0.3376 -0.0149 0.020 Uiso 1 1 calc R . . C19 C 0.45157(16) 0.36620(12) 0.26205(12) 0.0119(3) Uani 1 1 d . . . C24 C 0.55220(17) 0.32558(13) 0.30025(13) 0.0153(3) Uani 1 1 d . . . H24 H 0.5336 0.3230 0.3790 0.018 Uiso 1 1 calc R . . C32 C 0.13883(16) 0.26530(13) 0.46787(13) 0.0147(3) Uani 1 1 d . . . H32 H 0.1013 0.3186 0.5322 0.018 Uiso 1 1 calc R . . C23 C 0.67935(17) 0.28924(13) 0.22049(14) 0.0172(3) Uani 1 1 d . . . H23 H 0.7464 0.2621 0.2458 0.021 Uiso 1 1 calc R . . C30 C 0.31292(17) 0.36305(13) 0.56629(13) 0.0155(3) Uani 1 1 d . . . H30 H 0.3643 0.2879 0.5326 0.019 Uiso 1 1 calc R . . C26 C 0.17730(17) 0.55805(13) 0.55580(13) 0.0151(3) Uani 1 1 d . . . H26 H 0.1405 0.6134 0.5144 0.018 Uiso 1 1 calc R . . C34 C 0.15711(17) 0.08978(13) 0.37671(14) 0.0162(3) Uani 1 1 d . . . H34 H 0.1321 0.0252 0.3807 0.019 Uiso 1 1 calc R . . C25 C 0.25684(16) 0.44619(13) 0.50388(12) 0.0124(3) Uani 1 1 d . . . C35 C 0.24978(17) 0.10639(13) 0.27451(13) 0.0176(3) Uani 1 1 d . . . H35 H 0.2861 0.0534 0.2102 0.021 Uiso 1 1 calc R . . C29 C 0.29113(18) 0.39383(14) 0.67895(13) 0.0188(3) Uani 1 1 d . . . H29 H 0.3307 0.3399 0.7197 0.023 Uiso 1 1 calc R . . C33 C 0.10137(17) 0.16864(14) 0.47316(14) 0.0169(3) Uani 1 1 d . . . H33 H 0.0391 0.1570 0.5413 0.020 Uiso 1 1 calc R . . C36 C 0.28860(17) 0.20235(13) 0.26808(13) 0.0149(3) Uani 1 1 d . . . H36 H 0.3509 0.2136 0.1997 0.018 Uiso 1 1 calc R . . C22 C 0.70775(17) 0.29300(13) 0.10247(14) 0.0165(3) Uani 1 1 d . . . H22 H 0.7936 0.2676 0.0492 0.020 Uiso 1 1 calc R . . C27 C 0.15337(18) 0.58628(14) 0.66984(13) 0.0192(3) Uani 1 1 d . . . H27 H 0.0988 0.6601 0.7053 0.023 Uiso 1 1 calc R . . C18 C 0.10897(16) 0.51191(13) 0.25892(13) 0.0134(3) Uani 1 1 d . . . H18 H 0.0885 0.4444 0.2673 0.016 Uiso 1 1 calc R . . O7 O 0.52319(12) 1.12144(11) 0.61052(10) 0.0209(3) Uani 1 1 d . . . O4 O 1.08746(13) 1.36129(10) 0.06172(11) 0.0256(3) Uani 1 1 d . . . O6 O 0.66406(13) 1.19959(10) 0.61865(10) 0.0189(2) Uani 1 1 d . . . C2 C 0.92363(16) 1.07159(13) 0.28371(12) 0.0113(3) Uani 1 1 d . . . C6 C 0.78336(15) 0.97332(12) 0.27078(12) 0.0096(3) Uani 1 1 d . . . C3 C 0.83816(16) 1.11293(12) 0.39691(12) 0.0118(3) Uani 1 1 d . . . C28 C 0.21078(19) 0.50443(15) 0.73074(13) 0.0204(3) Uani 1 1 d . . . H28 H 0.1952 0.5239 0.8066 0.025 Uiso 1 1 calc R . . C11 C 1.37371(15) 0.98282(12) -0.11797(12) 0.0116(3) Uani 1 1 d . . . H11A H 1.4457 1.0114 -0.1439 0.014 Uiso 1 1 calc R . . H11B H 1.3902 0.9256 -0.1770 0.014 Uiso 1 1 calc R . . C16 C 0.08240(17) 0.70426(14) 0.19374(13) 0.0164(3) Uani 1 1 d . . . H16 H 0.0433 0.7653 0.1585 0.020 Uiso 1 1 calc R . . C7 C 0.62644(16) 1.13716(13) 0.56589(12) 0.0127(3) Uani 1 1 d . . . C4 C 0.72262(15) 1.08956(12) 0.44678(12) 0.0110(3) Uani 1 1 d . . . C17 C 0.05217(17) 0.60320(14) 0.20462(14) 0.0169(3) Uani 1 1 d . . . H17 H -0.0058 0.5965 0.1757 0.020 Uiso 1 1 calc R . . C9 C 1.10652(16) 1.25878(13) 0.03507(12) 0.0140(3) Uani 1 1 d . . . C15 C 0.17060(17) 0.71506(13) 0.23506(13) 0.0160(3) Uani 1 1 d . . . H15 H 0.1902 0.7830 0.2273 0.019 Uiso 1 1 calc R . . C5 C 0.69782(16) 1.01782(12) 0.38348(12) 0.0109(3) Uani 1 1 d . . . C14 C 0.22882(16) 0.62435(13) 0.28763(13) 0.0148(3) Uani 1 1 d . . . H14 H 0.2888 0.6305 0.3143 0.018 Uiso 1 1 calc R . . C1 C 0.89491(15) 1.00540(12) 0.21751(11) 0.0093(3) Uani 1 1 d . . . C8 C 1.23864(16) 1.11444(12) -0.21029(12) 0.0107(3) Uani 1 1 d . . . O1W O 0.47466(14) 0.72091(12) 0.17029(10) 0.0186(2) Uani 1 1 d . . . O2W O 0.29145(14) 0.43351(11) 0.97104(11) 0.0229(3) Uani 1 1 d . . . H3 H 0.860(2) 1.1568(18) 0.4384(18) 0.020(5) Uiso 1 1 d . . . H2 H 0.998(2) 1.0904(18) 0.2514(18) 0.019(5) Uiso 1 1 d . . . H02 H 0.606(3) 1.222(3) 0.690(3) 0.058(9) Uiso 1 1 d . . . H5 H 0.621(2) 0.9982(17) 0.4216(17) 0.017(5) Uiso 1 1 d . . . H1WB H 0.467(2) 0.7668(19) 0.1260(19) 0.019(5) Uiso 1 1 d . . . H2WA H 0.270(3) 0.502(2) 0.975(2) 0.041(7) Uiso 1 1 d . . . H1WA H 0.543(3) 0.674(3) 0.137(2) 0.042(8) Uiso 1 1 d . . . H2WB H 0.228(3) 0.412(2) 0.997(2) 0.046(8) Uiso 1 1 d . . . H8A H 1.3150(19) 1.1299(16) -0.2608(16) 0.011(4) Uiso 1 1 d . . . H8B H 1.164(2) 1.1866(17) -0.1900(16) 0.013(4) Uiso 1 1 d . . . Cu Cu 1.109347(18) 1.030153(14) 0.010897(14) 0.00935(5) Uani 1 1 d . . . P P 0.28407(4) 0.40478(3) 0.35927(3) 0.01032(8) 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 O1 0.0085(6) 0.0139(5) 0.0075(4) 0.0004(3) -0.0015(4) -0.0056(4) N 0.0081(7) 0.0092(5) 0.0085(5) 0.0000(4) -0.0021(5) -0.0034(5) O5 0.0131(7) 0.0186(5) 0.0193(5) 0.0038(4) -0.0089(5) -0.0039(5) O3 0.0114(6) 0.0151(5) 0.0119(4) 0.0027(4) -0.0043(4) -0.0049(5) O2 0.0112(7) 0.0127(5) 0.0187(5) -0.0022(4) -0.0013(5) -0.0038(5) C12 0.0124(9) 0.0104(6) 0.0130(6) -0.0001(5) -0.0057(6) -0.0043(6) C10 0.0142(9) 0.0122(6) 0.0119(6) -0.0002(5) -0.0044(6) -0.0074(6) C13 0.0107(9) 0.0123(6) 0.0099(6) 0.0008(5) -0.0034(6) -0.0027(6) C20 0.0151(9) 0.0174(7) 0.0131(6) 0.0015(5) -0.0061(6) -0.0069(7) C31 0.0118(9) 0.0110(6) 0.0126(6) 0.0012(5) -0.0059(6) -0.0038(6) C21 0.0163(10) 0.0185(7) 0.0142(6) 0.0002(5) -0.0038(6) -0.0074(7) C19 0.0108(9) 0.0118(6) 0.0124(6) 0.0002(5) -0.0041(6) -0.0036(6) C24 0.0154(9) 0.0154(7) 0.0160(7) 0.0019(5) -0.0081(6) -0.0045(7) C32 0.0138(9) 0.0134(6) 0.0135(6) -0.0008(5) -0.0026(6) -0.0037(6) C23 0.0145(10) 0.0144(7) 0.0241(8) 0.0021(6) -0.0103(7) -0.0036(7) C30 0.0173(9) 0.0160(7) 0.0143(6) 0.0017(5) -0.0071(6) -0.0061(7) C26 0.0176(10) 0.0141(6) 0.0136(6) -0.0003(5) -0.0056(6) -0.0059(7) C34 0.0175(10) 0.0131(6) 0.0224(7) 0.0033(5) -0.0120(7) -0.0060(7) C25 0.0135(9) 0.0142(6) 0.0103(6) 0.0002(5) -0.0045(6) -0.0056(6) C35 0.0219(10) 0.0155(7) 0.0173(7) -0.0020(5) -0.0092(7) -0.0064(7) C29 0.0252(10) 0.0234(8) 0.0145(7) 0.0072(6) -0.0110(7) -0.0135(8) C33 0.0157(10) 0.0168(7) 0.0168(7) 0.0024(5) -0.0037(6) -0.0074(7) C36 0.0153(9) 0.0167(7) 0.0117(6) -0.0013(5) -0.0038(6) -0.0060(7) C22 0.0107(9) 0.0145(7) 0.0202(7) -0.0011(5) -0.0013(6) -0.0049(7) C27 0.0241(10) 0.0186(7) 0.0150(7) -0.0027(5) -0.0052(7) -0.0098(7) C18 0.0109(9) 0.0136(6) 0.0146(6) -0.0002(5) -0.0049(6) -0.0030(6) O7 0.0125(7) 0.0313(6) 0.0158(5) -0.0063(4) 0.0013(5) -0.0109(6) O4 0.0202(8) 0.0139(5) 0.0332(7) -0.0090(5) 0.0012(6) -0.0070(5) O6 0.0182(7) 0.0259(6) 0.0117(5) -0.0058(4) -0.0004(5) -0.0122(5) C2 0.0099(9) 0.0152(6) 0.0102(6) 0.0022(5) -0.0037(6) -0.0066(6) C6 0.0092(8) 0.0105(6) 0.0096(6) 0.0014(4) -0.0039(5) -0.0040(6) C3 0.0125(9) 0.0139(6) 0.0106(6) 0.0011(5) -0.0052(6) -0.0058(6) C28 0.0289(11) 0.0260(8) 0.0125(6) 0.0012(6) -0.0084(7) -0.0165(8) C11 0.0094(8) 0.0126(6) 0.0116(6) 0.0009(5) -0.0035(6) -0.0029(6) C16 0.0103(9) 0.0163(7) 0.0153(7) 0.0036(5) -0.0024(6) 0.0005(7) C7 0.0129(9) 0.0136(6) 0.0109(6) 0.0007(5) -0.0045(6) -0.0040(6) C4 0.0101(8) 0.0131(6) 0.0084(6) 0.0007(5) -0.0027(5) -0.0036(6) C17 0.0123(9) 0.0189(7) 0.0182(7) 0.0014(5) -0.0076(6) -0.0021(7) C9 0.0143(9) 0.0129(6) 0.0128(6) -0.0008(5) -0.0029(6) -0.0048(6) C15 0.0154(10) 0.0128(6) 0.0159(7) 0.0021(5) -0.0032(6) -0.0039(7) C5 0.0095(9) 0.0127(6) 0.0105(6) 0.0016(5) -0.0034(6) -0.0045(6) C14 0.0145(9) 0.0150(7) 0.0161(6) 0.0019(5) -0.0065(6) -0.0060(7) C1 0.0087(8) 0.0091(6) 0.0086(6) 0.0012(4) -0.0030(5) -0.0019(6) C8 0.0118(9) 0.0116(6) 0.0100(6) 0.0022(5) -0.0045(6) -0.0056(6) O1W 0.0184(8) 0.0209(6) 0.0108(5) 0.0010(4) -0.0024(5) -0.0039(6) O2W 0.0204(8) 0.0153(6) 0.0279(6) -0.0005(5) -0.0033(6) -0.0072(6) Cu 0.00856(11) 0.01088(8) 0.00872(8) 0.00143(6) -0.00247(7) -0.00476(8) P 0.0113(2) 0.01048(16) 0.00928(15) 0.00041(12) -0.00437(14) -0.00346(15) _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 O1 C1 1.3422(16) . ? O1 Cu 1.9463(10) . ? O1 Cu 2.0572(10) 2_775 ? N C11 1.472(2) . ? N C10 1.4881(16) . ? N C8 1.4947(17) . ? N Cu 1.9866(12) . ? O5 C12 1.2377(19) . ? O3 C12 1.2815(19) . ? O3 Cu 1.9921(11) . ? O2 C9 1.2657(18) . ? O2 Cu 2.1221(11) . ? C12 C11 1.5283(19) . ? C10 C9 1.534(2) . ? C13 C18 1.395(2) . ? C13 C14 1.4014(19) . ? C13 P 1.7898(15) . ? C20 C21 1.385(2) . ? C20 C19 1.4056(19) . ? C31 C32 1.397(2) . ? C31 C36 1.400(2) . ? C31 P 1.7991(14) . ? C21 C22 1.389(2) . ? C19 C24 1.398(2) . ? C19 P 1.7962(17) . ? C24 C23 1.382(3) . ? C32 C33 1.3933(19) . ? C23 C22 1.392(2) . ? C30 C29 1.392(2) . ? C30 C25 1.403(2) . ? C26 C27 1.393(2) . ? C26 C25 1.397(2) . ? C34 C35 1.387(2) . ? C34 C33 1.388(2) . ? C25 P 1.7957(14) . ? C35 C36 1.393(2) . ? C29 C28 1.386(3) . ? C27 C28 1.389(2) . ? C18 C17 1.395(2) . ? O7 C7 1.2160(19) . ? O4 C9 1.2432(17) . ? O6 C7 1.3294(16) . ? C2 C3 1.387(2) . ? C2 C1 1.4059(17) . ? C6 C5 1.390(2) . ? C6 C1 1.4152(19) . ? C6 C8 1.5051(17) 2_775 ? C3 C4 1.396(2) . ? C16 C17 1.391(2) . ? C16 C15 1.394(2) . ? C7 C4 1.485(2) . ? C4 C5 1.3974(18) . ? C15 C14 1.384(2) . ? C8 C6 1.5051(17) 2_775 ? Cu O1 2.0572(10) 2_775 ? 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 C1 O1 Cu 125.30(8) . . ? C1 O1 Cu 119.90(9) . 2_775 ? Cu O1 Cu 99.80(4) . 2_775 ? C11 N C10 110.13(11) . . ? C11 N C8 112.31(11) . . ? C10 N C8 108.70(10) . . ? C11 N Cu 106.60(8) . . ? C10 N Cu 105.12(9) . . ? C8 N Cu 113.72(9) . . ? C12 O3 Cu 113.77(9) . . ? C9 O2 Cu 110.72(10) . . ? O5 C12 O3 125.71(13) . . ? O5 C12 C11 118.32(14) . . ? O3 C12 C11 115.96(13) . . ? N C10 C9 111.88(12) . . ? C18 C13 C14 120.75(13) . . ? C18 C13 P 121.42(11) . . ? C14 C13 P 117.57(11) . . ? C21 C20 C19 119.73(15) . . ? C32 C31 C36 120.32(13) . . ? C32 C31 P 119.69(11) . . ? C36 C31 P 119.99(11) . . ? C20 C21 C22 120.11(14) . . ? C24 C19 C20 119.86(15) . . ? C24 C19 P 122.44(11) . . ? C20 C19 P 117.61(12) . . ? C23 C24 C19 119.73(14) . . ? C33 C32 C31 119.61(14) . . ? C24 C23 C22 120.39(15) . . ? C29 C30 C25 119.49(15) . . ? C27 C26 C25 119.70(14) . . ? C35 C34 C33 120.60(13) . . ? C26 C25 C30 120.01(13) . . ? C26 C25 P 120.93(11) . . ? C30 C25 P 119.02(11) . . ? C34 C35 C36 120.10(14) . . ? C28 C29 C30 120.32(15) . . ? C34 C33 C32 119.95(15) . . ? C35 C36 C31 119.43(14) . . ? C21 C22 C23 120.17(16) . . ? C28 C27 C26 120.16(15) . . ? C17 C18 C13 119.16(13) . . ? C3 C2 C1 120.32(13) . . ? C5 C6 C1 119.23(12) . . ? C5 C6 C8 119.73(12) . 2_775 ? C1 C6 C8 120.89(13) . 2_775 ? C2 C3 C4 120.64(12) . . ? C29 C28 C27 120.27(14) . . ? N C11 C12 108.50(12) . . ? C17 C16 C15 120.74(14) . . ? O7 C7 O6 123.28(14) . . ? O7 C7 C4 123.48(13) . . ? O6 C7 C4 113.24(13) . . ? C3 C4 C5 119.01(13) . . ? C3 C4 C7 121.84(12) . . ? C5 C4 C7 119.13(13) . . ? C16 C17 C18 119.94(14) . . ? O4 C9 O2 126.14(16) . . ? O4 C9 C10 117.12(13) . . ? O2 C9 C10 116.68(12) . . ? C14 C15 C16 119.75(13) . . ? C6 C5 C4 121.30(13) . . ? C15 C14 C13 119.64(14) . . ? O1 C1 C2 121.18(13) . . ? O1 C1 C6 119.71(11) . . ? C2 C1 C6 119.12(13) . . ? N C8 C6 114.69(11) . 2_775 ? O1 Cu N 174.03(4) . . ? O1 Cu O3 99.01(4) . . ? N Cu O3 82.73(5) . . ? O1 Cu O1 80.20(4) . 2_775 ? N Cu O1 95.07(4) . 2_775 ? O3 Cu O1 144.77(4) . 2_775 ? O1 Cu O2 101.50(4) . . ? N Cu O2 82.71(5) . . ? O3 Cu O2 115.94(4) . . ? O1 Cu O2 98.48(4) 2_775 . ? C13 P C25 110.68(7) . . ? C13 P C19 105.92(7) . . ? C25 P C19 112.19(7) . . ? C13 P C31 111.12(7) . . ? C25 P C31 107.73(6) . . ? C19 P C31 109.22(7) . . ? _diffrn_measured_fraction_theta_max 0.819 _diffrn_reflns_theta_full 31.12 _diffrn_measured_fraction_theta_full 0.819 _refine_diff_density_max 0.503 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.065 # Attachment 'Cu8_complex.cif' data_Cu8 _database_code_depnum_ccdc_archive 'CCDC 680998' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 Cu N2 O7' _chemical_formula_weight 444.95 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.629(12) _cell_length_b 16.71(3) _cell_length_c 11.39(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.76(13) _cell_angle_gamma 90.00 _cell_volume 1879(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.379 _exptl_crystal_size_mid 0.266 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.207 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.886 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 6354 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 30.29 _reflns_number_total 4177 _reflns_number_gt 2939 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1277P)^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 4177 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.2152 _refine_ls_wR_factor_gt 0.1837 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.002 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 Cu Cu 0.50673(5) 0.08872(3) 0.51704(5) 0.0181(2) Uani 1 1 d . . . O5 O 0.4758(3) 0.2239(2) 0.8023(3) 0.0246(7) Uani 1 1 d . . . O4 O 0.5866(3) 0.24499(19) 0.2967(3) 0.0247(7) Uani 1 1 d . . . O7 O 1.2513(3) -0.0525(2) 0.6684(3) 0.0260(7) Uani 1 1 d . . . O6 O 0.2383(3) 0.07377(19) 0.7270(3) 0.0238(7) Uani 1 1 d . . . H02 H 0.3188 0.0742 0.7370 0.036 Uiso 1 1 calc R . . O2 O 0.4470(3) 0.1204(2) 0.6699(3) 0.0255(7) Uani 1 1 d . . . O3 O 0.4722(3) 0.1660(2) 0.3784(3) 0.0251(8) Uani 1 1 d . . . O1 O 0.3758(3) 0.00987(17) 0.4238(3) 0.0192(7) Uani 1 1 d . . . N N 0.6560(3) 0.1637(2) 0.6055(3) 0.0169(8) Uani 1 1 d . . . C5 C 0.9717(4) 0.0597(2) 0.6951(3) 0.0165(9) Uani 1 1 d . . . H5 H 1.0201 0.1057 0.7322 0.020 Uiso 1 1 calc R . . C2 C 0.1708(4) 0.0746(3) 0.4159(4) 0.0185(9) Uani 1 1 d . . . H2 H 0.2186 0.1209 0.4528 0.022 Uiso 1 1 calc R . . C11 C 0.5931(4) 0.2247(2) 0.6599(4) 0.0177(9) Uani 1 1 d . . . H11A H 0.5422 0.2615 0.5940 0.021 Uiso 1 1 calc R . . H11B H 0.6638 0.2552 0.7240 0.021 Uiso 1 1 calc R . . N2 N 0.3120(4) 0.1915(2) 0.1142(3) 0.0216(8) Uani 1 1 d . . . C6 C 0.8339(4) 0.0570(3) 0.6692(3) 0.0177(9) Uani 1 1 d . . . C9 C 0.7013(4) 0.1964(3) 0.5072(4) 0.0178(9) Uani 1 1 d . . . H9A H 0.7668 0.1609 0.4943 0.021 Uiso 1 1 calc R . . H9B H 0.7442 0.2483 0.5337 0.021 Uiso 1 1 calc R . . C7 C 1.1857(4) 0.0013(2) 0.6879(4) 0.0172(9) Uani 1 1 d . . . C13 C 0.3127(5) 0.3386(3) 0.0719(4) 0.0336(12) Uani 1 1 d . . . H13A H 0.2568 0.3853 0.0532 0.050 Uiso 1 1 calc R . . H13B H 0.3448 0.3290 0.0047 0.050 Uiso 1 1 calc R . . H13C H 0.3885 0.3469 0.1496 0.050 Uiso 1 1 calc R . . C8 C 0.7666(4) 0.1240(3) 0.7112(4) 0.0195(9) Uani 1 1 d . . . H8A H 0.7291 0.1031 0.7708 0.023 Uiso 1 1 calc R . . H8B H 0.8347 0.1639 0.7553 0.023 Uiso 1 1 calc R . . C10 C 0.5778(4) 0.2045(3) 0.3840(4) 0.0204(9) Uani 1 1 d . . . C14 C 0.2314(5) 0.2677(3) 0.0845(4) 0.0303(11) Uani 1 1 d . . . H14A H 0.1539 0.2604 0.0063 0.036 Uiso 1 1 calc R . . H14B H 0.1975 0.2784 0.1512 0.036 Uiso 1 1 calc R . . C16 C 0.2317(5) 0.1267(3) 0.1464(4) 0.0277(11) Uani 1 1 d . . . H16A H 0.1934 0.1481 0.2049 0.033 Uiso 1 1 calc R . . H16B H 0.2925 0.0839 0.1890 0.033 Uiso 1 1 calc R . . C4 C 1.0405(5) -0.0030(3) 0.6682(4) 0.0194(10) Uani 1 1 d . . . C3 C 0.0332(4) 0.0711(3) 0.3854(4) 0.0190(9) Uani 1 1 d . . . H3 H -0.0111 0.1152 0.4012 0.023 Uiso 1 1 calc R . . C17 C 0.4507(6) 0.0957(3) 0.0462(5) 0.0373(14) Uani 1 1 d . . . H17A H 0.4817 0.0837 -0.0209 0.056 Uiso 1 1 calc R . . H17B H 0.3981 0.0514 0.0573 0.056 Uiso 1 1 calc R . . H17C H 0.5272 0.1049 0.1231 0.056 Uiso 1 1 calc R . . C12 C 0.4995(4) 0.1878(3) 0.7182(4) 0.0212(10) Uani 1 1 d . . . C18 C 0.3645(5) 0.1693(3) 0.0137(4) 0.0295(11) Uani 1 1 d . . . H18A H 0.4177 0.2136 0.0012 0.035 Uiso 1 1 calc R . . H18B H 0.2886 0.1601 -0.0652 0.035 Uiso 1 1 calc R . . C15 C 0.1185(6) 0.0922(3) 0.0325(5) 0.0369(13) Uani 1 1 d . . . H15A H 0.0708 0.0516 0.0595 0.055 Uiso 1 1 calc R . . H15B H 0.1558 0.0692 -0.0246 0.055 Uiso 1 1 calc R . . H15C H 0.0570 0.1340 -0.0095 0.055 Uiso 1 1 calc R . . C1 C 0.2400(4) 0.0096(2) 0.3921(4) 0.0177(9) 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 Cu 0.0122(3) 0.0242(3) 0.0162(3) -0.00162(18) 0.0036(2) -0.00264(18) O5 0.0236(18) 0.0351(18) 0.0177(14) -0.0025(12) 0.0106(13) 0.0034(13) O4 0.0268(18) 0.0307(17) 0.0176(14) 0.0018(12) 0.0093(13) -0.0009(13) O7 0.0163(16) 0.0349(19) 0.0299(16) -0.0008(14) 0.0119(14) 0.0028(13) O6 0.0146(16) 0.0318(17) 0.0267(16) -0.0069(13) 0.0097(13) -0.0012(12) O2 0.0194(16) 0.0332(18) 0.0247(15) -0.0068(13) 0.0092(13) -0.0041(14) O3 0.0154(16) 0.0369(18) 0.0185(13) 0.0045(13) 0.0010(12) -0.0048(13) O1 0.0111(15) 0.0244(16) 0.0213(13) -0.0022(11) 0.0053(12) -0.0052(11) N 0.0102(17) 0.0276(18) 0.0125(14) -0.0017(13) 0.0039(13) -0.0020(13) C5 0.017(2) 0.0186(19) 0.0118(16) 0.0014(14) 0.0026(15) -0.0021(15) C2 0.015(2) 0.022(2) 0.0179(18) 0.0019(15) 0.0057(16) -0.0011(15) C11 0.014(2) 0.023(2) 0.0182(18) -0.0092(15) 0.0092(16) 0.0000(16) N2 0.0177(19) 0.031(2) 0.0155(15) -0.0026(14) 0.0057(14) 0.0013(15) C6 0.013(2) 0.029(2) 0.0127(17) 0.0022(15) 0.0064(15) 0.0009(16) C9 0.016(2) 0.021(2) 0.0172(18) 0.0012(15) 0.0071(16) -0.0033(15) C7 0.011(2) 0.027(2) 0.0147(17) 0.0007(15) 0.0068(15) 0.0003(15) C13 0.031(3) 0.043(3) 0.030(2) 0.004(2) 0.015(2) 0.001(2) C8 0.015(2) 0.029(2) 0.0126(17) -0.0028(16) 0.0028(15) 0.0010(16) C10 0.020(2) 0.024(2) 0.0168(18) -0.0058(16) 0.0061(17) 0.0017(17) C14 0.022(3) 0.047(3) 0.021(2) 0.003(2) 0.0075(19) 0.001(2) C16 0.030(3) 0.035(3) 0.0177(19) -0.0003(18) 0.0094(18) -0.004(2) C4 0.014(2) 0.032(2) 0.0133(17) 0.0008(15) 0.0063(16) -0.0004(16) C3 0.014(2) 0.032(2) 0.0143(18) 0.0013(16) 0.0092(16) -0.0007(17) C17 0.033(3) 0.044(3) 0.035(3) -0.008(2) 0.012(2) 0.006(2) C12 0.014(2) 0.030(2) 0.0161(18) -0.0001(16) 0.0006(16) 0.0050(17) C18 0.022(3) 0.049(3) 0.022(2) -0.004(2) 0.0141(19) 0.002(2) C15 0.024(3) 0.051(3) 0.032(3) -0.008(2) 0.007(2) -0.009(2) C1 0.014(2) 0.025(2) 0.0125(16) 0.0027(14) 0.0035(15) 0.0006(15) _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 Cu O1 1.914(5) . ? Cu N 1.968(5) . ? Cu O3 1.972(5) . ? Cu O1 2.036(5) 3_656 ? Cu O2 2.130(5) . ? Cu Cu 2.984(6) 3_656 ? O5 C12 1.233(6) . ? O4 C10 1.235(6) . ? O7 C7 1.212(6) . ? O6 C7 1.333(6) 1_455 ? O2 C12 1.280(6) . ? O3 C10 1.271(6) . ? O1 C1 1.352(6) . ? O1 Cu 2.036(5) 3_656 ? N C11 1.478(6) . ? N C9 1.478(6) . ? N C8 1.497(6) . ? C5 C4 1.379(7) . ? C5 C6 1.383(6) . ? C2 C3 1.373(6) . ? C2 C1 1.399(7) . ? C11 C12 1.515(7) . ? N2 C18 1.495(6) . ? N2 C16 1.502(7) . ? N2 C14 1.509(7) . ? C6 C1 1.384(6) 3_656 ? C6 C8 1.503(7) . ? C9 C10 1.533(6) . ? C7 O6 1.333(6) 1_655 ? C7 C4 1.476(7) . ? C13 C14 1.498(7) . ? C16 C15 1.513(7) . ? C4 C3 1.381(6) 3_656 ? C3 C4 1.381(6) 3_656 ? C17 C18 1.504(8) . ? C1 C6 1.384(6) 3_656 ? 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 Cu N 173.36(15) . . ? O1 Cu O3 97.0(2) . . ? N Cu O3 82.6(2) . . ? O1 Cu O1 81.9(2) . 3_656 ? N Cu O1 93.6(2) . 3_656 ? O3 Cu O1 135.42(18) . 3_656 ? O1 Cu O2 104.33(19) . . ? N Cu O2 81.55(19) . . ? O3 Cu O2 117.88(19) . . ? O1 Cu O2 105.29(19) 3_656 . ? O1 Cu Cu 42.49(14) . 3_656 ? N Cu Cu 132.87(16) . 3_656 ? O3 Cu Cu 124.37(17) . 3_656 ? O1 Cu Cu 39.42(13) 3_656 3_656 ? O2 Cu Cu 109.80(16) . 3_656 ? C12 O2 Cu 110.8(3) . . ? C10 O3 Cu 113.0(3) . . ? C1 O1 Cu 128.9(3) . . ? C1 O1 Cu 123.8(3) . 3_656 ? Cu O1 Cu 98.1(2) . 3_656 ? C11 N C9 112.7(4) . . ? C11 N C8 108.6(3) . . ? C9 N C8 113.4(4) . . ? C11 N Cu 104.2(3) . . ? C9 N Cu 105.7(3) . . ? C8 N Cu 111.8(3) . . ? C4 C5 C6 122.8(4) . . ? C3 C2 C1 120.9(4) . . ? N C11 C12 112.1(4) . . ? C18 N2 C16 114.6(4) . . ? C18 N2 C14 112.5(4) . . ? C16 N2 C14 109.8(4) . . ? C5 C6 C1 118.9(4) . 3_656 ? C5 C6 C8 120.5(4) . . ? C1 C6 C8 120.6(4) 3_656 . ? N C9 C10 108.8(4) . . ? O7 C7 O6 122.5(4) . 1_655 ? O7 C7 C4 125.7(4) . . ? O6 C7 C4 111.8(4) 1_655 . ? N C8 C6 114.0(3) . . ? O4 C10 O3 124.3(4) . . ? O4 C10 C9 119.8(4) . . ? O3 C10 C9 115.9(4) . . ? C13 C14 N2 112.9(4) . . ? N2 C16 C15 113.6(4) . . ? C5 C4 C3 117.5(4) . 3_656 ? C5 C4 C7 123.2(4) . . ? C3 C4 C7 119.2(4) 3_656 . ? C2 C3 C4 121.0(4) . 3_656 ? O5 C12 O2 125.3(5) . . ? O5 C12 C11 120.0(4) . . ? O2 C12 C11 114.6(4) . . ? N2 C18 C17 112.5(4) . . ? O1 C1 C6 118.7(4) . 3_656 ? O1 C1 C2 122.7(4) . . ? C6 C1 C2 118.6(4) 3_656 . ? _diffrn_measured_fraction_theta_max 0.744 _diffrn_reflns_theta_full 30.29 _diffrn_measured_fraction_theta_full 0.744 _refine_diff_density_max 1.556 _refine_diff_density_min -2.364 _refine_diff_density_rms 0.150 # Attachment 'Cu9_complex.cif' data_Cu9 _database_code_depnum_ccdc_archive 'CCDC 680999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Cu2 K N2 Na O22' _chemical_formula_weight 851.57 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7363(6) _cell_length_b 15.9304(12) _cell_length_c 22.977(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.122(8) _cell_angle_gamma 90.00 _cell_volume 3137.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.525 _exptl_crystal_size_mid 0.268 _exptl_crystal_size_min 0.101 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 1.599 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.643 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _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 31738 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1032 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.10 _reflns_number_total 5568 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1634P)^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 5568 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2376 _refine_ls_wR_factor_gt 0.2016 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C9' C 0.8085(9) 0.4088(6) 0.9138(4) 0.0156(19) Uani 1 1 d . . . C8' C 0.8820(9) 0.4833(6) 0.8874(4) 0.0155(19) Uani 1 1 d . . . O6W O 0.6127(16) 0.1829(9) 0.8254(7) 0.119(5) Uani 1 1 d . . . O7W O 0.7794(17) 0.1815(10) 0.8022(6) 0.127(5) Uani 1 1 d . . . O3W O 0.415(3) 0.0782(14) 0.0046(9) 0.203(10) Uani 1 1 d . . . Cu1 Cu 0.33713(11) 0.36245(7) 0.74847(4) 0.0144(3) Uani 1 1 d . . . Cu1' Cu 0.68923(11) 0.40155(7) 0.78626(4) 0.0131(3) Uani 1 1 d . . . Na1 Na 0.4999(4) 0.2695(3) 0.91228(17) 0.0333(10) Uani 1 1 d . . . K1 K 0.9057(7) 0.1681(4) 0.8935(3) 0.134(2) Uani 1 1 d . . . O4' O 0.8412(7) 0.4037(4) 0.9706(3) 0.0211(15) Uani 1 1 d . . . O6' O 0.5817(7) 0.3644(4) 1.0113(3) 0.0217(14) Uani 1 1 d . . . O3 O 0.2904(8) 0.2900(4) 0.8128(3) 0.0246(15) Uani 1 1 d . . . O5' O 0.1015(7) 0.4448(4) 0.7474(3) 0.0207(14) Uani 1 1 d . . . O1 O 1.0836(6) 0.1928(4) 1.2418(2) 0.0143(13) Uani 1 1 d . . . O3' O 0.8963(6) 0.3776(4) 0.7701(3) 0.0164(13) Uani 1 1 d . . . O2' O 0.7321(7) 0.3563(4) 0.8811(3) 0.0216(15) Uani 1 1 d . . . O4 O 0.2474(8) 0.4113(5) 0.5760(3) 0.0356(18) Uani 1 1 d . . . O6 O 1.0539(8) 0.2846(5) 1.0065(3) 0.0322(18) Uani 1 1 d . . . O1W O 0.3709(9) 0.0791(5) 0.8219(3) 0.0367(18) Uani 1 1 d . . . O2 O 0.3388(7) 0.4219(4) 0.6728(3) 0.0178(14) Uani 1 1 d . . . N1' N 0.8026(8) 0.5042(4) 0.8269(3) 0.0126(15) Uani 1 1 d . . . O8W O 0.8785(9) 0.0116(5) 0.8274(4) 0.044(2) Uani 1 1 d . . . N1 N 0.2220(8) 0.2722(5) 0.6967(3) 0.0174(17) Uani 1 1 d . . . C4' C 0.5667(9) 0.4151(6) 1.0590(4) 0.016(2) Uani 1 1 d . . . O1' O 0.4800(6) 0.4414(4) 0.7945(3) 0.0176(14) Uani 1 1 d . . . C5 C 0.9524(10) 0.2903(6) 1.0971(4) 0.019(2) Uani 1 1 d . . . H5 H 0.8728 0.3258 1.0791 0.022 Uiso 1 1 calc R . . O5 O 1.1172(9) 0.1962(5) 0.8299(4) 0.047(2) Uani 1 1 d . . . C2' C 0.6501(10) 0.5300(6) 1.1249(4) 0.0170(19) Uani 1 1 d . . . H2' H 0.7180 0.5746 1.1364 0.020 Uiso 1 1 calc R . . C11' C -0.0211(9) 0.4430(6) 0.7676(3) 0.016(2) Uani 1 1 d . . . C3' C 0.6670(9) 0.4823(6) 1.0760(4) 0.0142(19) Uani 1 1 d . . . H3' H 0.7447 0.4950 1.0548 0.017 Uiso 1 1 calc R . . C6' C 0.4347(9) 0.4458(5) 1.1392(4) 0.0124(18) Uani 1 1 d . . . C10' C 0.9195(10) 0.5236(6) 0.7896(4) 0.0172(19) Uani 1 1 d . . . H1'A H 1.0057 0.5548 0.8127 0.021 Uiso 1 1 calc R . . H1'B H 0.8719 0.5580 0.7561 0.021 Uiso 1 1 calc R . . C4 C 1.0608(10) 0.2616(6) 1.0644(4) 0.021(2) Uani 1 1 d . . . C6 C 0.9600(9) 0.2670(6) 1.1560(4) 0.0156(19) Uani 1 1 d . . . C7 C 0.3343(10) 0.2040(6) 0.6877(4) 0.018(2) Uani 1 1 d . . . H7A H 0.3827 0.1816 0.7261 0.022 Uiso 1 1 calc R . . H7B H 0.2765 0.1589 0.6651 0.022 Uiso 1 1 calc R . . C3 C 1.1789(10) 0.2100(6) 1.0920(4) 0.019(2) Uani 1 1 d . . . H3 H 1.2530 0.1908 1.0711 0.023 Uiso 1 1 calc R . . C2 C 1.1893(10) 0.1857(6) 1.1518(4) 0.017(2) Uani 1 1 d . . . H2 H 1.2693 0.1503 1.1696 0.020 Uiso 1 1 calc R . . C5' C 0.4509(10) 0.3977(6) 1.0896(4) 0.0178(19) Uani 1 1 d . . . H5' H 0.3824 0.3536 1.0774 0.021 Uiso 1 1 calc R . . O10W O 1.1075(13) 0.0418(6) 0.9643(4) 0.069(3) Uani 1 1 d . . . C1 C 1.0801(10) 0.2146(6) 1.1846(4) 0.0146(19) Uani 1 1 d . . . C8 C 0.1535(10) 0.3141(6) 0.6403(4) 0.022(2) Uani 1 1 d . . . H8A H 0.0501 0.3345 0.6424 0.027 Uiso 1 1 calc R . . H8B H 0.1431 0.2738 0.6081 0.027 Uiso 1 1 calc R . . C7' C 0.6900(10) 0.5763(5) 0.8263(4) 0.0154(19) Uani 1 1 d . . . H7'A H 0.7463 0.6256 0.8435 0.018 Uiso 1 1 calc R . . H7'B H 0.6419 0.5895 0.7856 0.018 Uiso 1 1 calc R . . C10 C 0.1100(11) 0.2370(6) 0.7306(5) 0.029(2) Uani 1 1 d . . . H1A H 0.0864 0.1793 0.7187 0.035 Uiso 1 1 calc R . . H1B H 0.0137 0.2689 0.7223 0.035 Uiso 1 1 calc R . . O9W O 0.8551(10) 0.0148(6) 0.9355(4) 0.055(2) Uani 1 1 d . . . C9 C 0.2534(10) 0.3866(6) 0.6277(4) 0.022(2) Uani 1 1 d . . . O2W O 0.3960(13) 0.0017(7) 0.0950(6) 0.104(5) Uani 1 1 d . . . C11 C 0.1772(12) 0.2402(6) 0.7963(5) 0.031(3) Uani 1 1 d . . . C1' C 0.4649(9) 0.4870(6) 0.8432(4) 0.016(2) Uani 1 1 d . . . O4W O 0.262(3) 0.2081(10) 0.9428(6) 0.205(11) Uani 1 1 d . . . O5W O 0.751(2) 0.1562(7) 0.9661(4) 0.155(8) Uani 1 1 d . . . H8'A H 0.8052 0.1760 1.0046 0.186 Uiso 1 1 calc R . . H8'B H 0.7146 0.0993 0.9695 0.186 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9' 0.009(4) 0.017(5) 0.023(5) -0.004(4) 0.007(4) 0.008(4) C8' 0.010(4) 0.020(5) 0.016(4) 0.003(4) 0.002(3) -0.007(4) O6W 0.089(10) 0.095(11) 0.165(14) -0.019(10) 0.007(9) -0.004(8) O7W 0.101(11) 0.132(13) 0.137(12) -0.011(10) -0.006(9) -0.011(10) O3W 0.27(3) 0.19(2) 0.173(18) 0.041(15) 0.105(17) 0.089(19) Cu1 0.0125(6) 0.0146(7) 0.0173(6) -0.0030(4) 0.0053(4) -0.0011(4) Cu1' 0.0085(5) 0.0148(6) 0.0165(6) -0.0030(4) 0.0037(4) 0.0004(4) Na1 0.030(2) 0.042(3) 0.027(2) 0.0018(19) 0.0028(17) -0.0059(19) K1 0.118(4) 0.150(5) 0.138(4) 0.011(4) 0.034(3) 0.007(4) O4' 0.017(3) 0.032(4) 0.014(3) 0.003(3) 0.003(2) 0.001(3) O6' 0.020(3) 0.020(4) 0.026(3) -0.009(3) 0.007(3) 0.001(3) O3 0.033(4) 0.019(4) 0.026(4) 0.001(3) 0.015(3) 0.005(3) O5' 0.018(3) 0.020(4) 0.028(3) -0.002(3) 0.013(3) 0.000(3) O1 0.010(3) 0.016(4) 0.019(3) 0.003(3) 0.009(2) 0.004(2) O3' 0.010(3) 0.018(4) 0.023(3) -0.002(3) 0.006(2) 0.002(3) O2' 0.022(3) 0.023(4) 0.020(3) 0.001(3) 0.004(3) -0.005(3) O4 0.047(5) 0.039(5) 0.017(4) 0.001(3) -0.004(3) 0.009(4) O6 0.045(4) 0.036(5) 0.018(3) 0.011(3) 0.012(3) 0.013(4) O1W 0.045(5) 0.020(4) 0.051(5) 0.001(3) 0.025(4) 0.000(3) O2 0.014(3) 0.019(4) 0.021(3) -0.002(3) 0.004(3) -0.001(3) N1' 0.013(4) 0.011(4) 0.014(4) 0.003(3) 0.005(3) 0.000(3) O8W 0.040(5) 0.034(5) 0.058(5) 0.000(4) 0.013(4) 0.008(4) N1 0.009(4) 0.016(4) 0.030(4) -0.002(3) 0.011(3) -0.003(3) C4' 0.007(4) 0.022(6) 0.019(5) 0.003(4) 0.002(3) 0.006(4) O1' 0.012(3) 0.020(4) 0.022(3) -0.007(3) 0.008(2) -0.001(3) C5 0.013(4) 0.018(5) 0.023(5) 0.007(4) -0.002(4) 0.000(4) O5 0.051(5) 0.036(5) 0.069(6) 0.019(4) 0.047(4) 0.005(4) C2' 0.016(4) 0.014(5) 0.021(5) 0.000(4) 0.004(4) -0.004(4) C11' 0.009(4) 0.027(6) 0.012(4) -0.001(4) 0.004(3) 0.000(4) C3' 0.011(4) 0.016(5) 0.016(4) 0.004(4) 0.005(3) 0.003(4) C6' 0.005(4) 0.013(5) 0.019(4) 0.003(4) 0.003(3) 0.001(3) C10' 0.022(5) 0.012(5) 0.018(5) 0.002(4) 0.004(4) 0.001(4) C4 0.019(5) 0.025(6) 0.018(5) 0.004(4) 0.002(4) -0.004(4) C6 0.007(4) 0.021(5) 0.020(5) 0.000(4) 0.004(3) -0.005(4) C7 0.018(5) 0.014(5) 0.024(5) -0.005(4) 0.007(4) -0.002(4) C3 0.017(5) 0.023(6) 0.022(5) -0.004(4) 0.012(4) 0.003(4) C2 0.009(4) 0.022(6) 0.018(5) 0.000(4) 0.001(3) -0.003(4) C5' 0.016(5) 0.013(5) 0.023(5) -0.006(4) 0.001(4) -0.002(4) O10W 0.129(9) 0.037(6) 0.048(5) 0.001(4) 0.039(6) -0.004(5) C1 0.020(5) 0.009(5) 0.015(4) 0.000(3) 0.006(4) -0.001(4) C8 0.013(5) 0.027(6) 0.026(5) -0.011(4) 0.002(4) 0.004(4) C7' 0.020(5) 0.007(5) 0.020(5) 0.001(4) 0.008(4) 0.000(4) C10 0.022(5) 0.014(6) 0.057(7) -0.009(5) 0.022(5) -0.002(4) O9W 0.066(6) 0.053(6) 0.047(5) -0.003(4) 0.015(4) -0.017(5) C9 0.016(5) 0.023(6) 0.024(5) -0.004(4) -0.001(4) 0.010(4) O2W 0.083(8) 0.049(7) 0.145(11) -0.014(7) -0.068(8) 0.003(6) C11 0.036(6) 0.012(6) 0.055(7) 0.003(5) 0.032(5) 0.003(5) C1' 0.011(4) 0.020(5) 0.017(4) 0.002(4) 0.002(3) 0.009(4) O4W 0.45(3) 0.120(13) 0.078(9) 0.057(9) 0.136(14) 0.179(17) O5W 0.39(3) 0.045(7) 0.031(6) 0.010(5) 0.049(9) 0.056(11) _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 C9' O2' 1.230(10) . ? C9' O4' 1.283(10) . ? C9' C8' 1.529(13) . ? C8' N1' 1.468(11) . ? O6W O7W 1.645(19) . ? O6W K1 2.740(15) . ? O6W Na1 2.759(16) . ? O7W K1 2.184(15) . ? Cu1 O1' 1.936(6) . ? Cu1 O3 1.978(6) . ? Cu1 O2 1.983(6) . ? Cu1 N1 2.009(7) . ? Cu1 O1 2.358(6) 4_565 ? Cu1 O5' 2.437(6) . ? Cu1' O1 1.947(6) 4_565 ? Cu1' O3' 1.953(5) . ? Cu1' O1' 1.978(6) . ? Cu1' N1' 2.042(7) . ? Cu1' O2' 2.257(6) . ? Na1 O4W 2.52(2) . ? Na1 O3 2.659(7) . ? Na1 O2' 2.665(7) . ? Na1 O6' 2.710(7) . ? Na1 O5W 2.926(15) . ? Na1 K1 3.994(7) . ? K1 O5W 2.347(15) . ? K1 O5 2.604(9) . ? K1 O9W 2.694(11) . ? K1 O8W 2.906(10) . ? K1 O10W 2.949(12) . ? K1 O4W 3.16(3) 1_655 ? K1 O6 3.250(10) . ? K1 O2' 3.347(9) . ? O6' C4' 1.388(10) . ? O3 C11 1.268(12) . ? O5' C11' 1.248(10) . ? O1 C1 1.355(10) . ? O1 Cu1' 1.947(6) 4_666 ? O1 Cu1 2.358(5) 4_666 ? O3' C11' 1.275(11) 1_655 ? O4 C9 1.241(11) . ? O6 C4 1.371(10) . ? O2 C9 1.284(11) . ? N1' C10' 1.487(11) . ? N1' C7' 1.510(11) . ? N1 C10 1.475(11) . ? N1 C8 1.477(12) . ? N1 C7 1.504(11) . ? C4' C5' 1.368(12) . ? C4' C3' 1.391(12) . ? O1' C1' 1.363(10) . ? C5 C6 1.393(12) . ? C5 C4 1.394(12) . ? O5 C11 1.234(12) 1_655 ? C2' C1' 1.380(12) 3_667 ? C2' C3' 1.388(12) . ? C11' O3' 1.275(11) 1_455 ? C11' C10' 1.509(13) 1_455 ? C6' C1' 1.393(12) 3_667 ? C6' C5' 1.403(12) . ? C6' C7' 1.508(11) 3_667 ? C10' C11' 1.509(13) 1_655 ? C4 C3 1.375(13) . ? C6 C1 1.401(12) . ? C6 C7 1.502(12) 4_666 ? C7 C6 1.502(12) 4_565 ? C3 C2 1.412(12) . ? C2 C1 1.402(12) . ? C8 C9 1.510(14) . ? C7' C6' 1.508(11) 3_667 ? C10 C11 1.509(15) . ? C11 O5 1.234(12) 1_455 ? C1' C2' 1.380(12) 3_667 ? C1' C6' 1.393(12) 3_667 ? O4W K1 3.16(3) 1_455 ? 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' C9' O4' 124.4(9) . . ? O2' C9' C8' 120.3(8) . . ? O4' C9' C8' 115.1(8) . . ? N1' C8' C9' 113.2(7) . . ? O7W O6W K1 52.9(6) . . ? O7W O6W Na1 134.7(9) . . ? K1 O6W Na1 93.1(5) . . ? O6W O7W K1 90.3(9) . . ? O1' Cu1 O3 100.1(3) . . ? O1' Cu1 O2 93.2(3) . . ? O3 Cu1 O2 166.2(3) . . ? O1' Cu1 N1 170.1(3) . . ? O3 Cu1 N1 82.7(3) . . ? O2 Cu1 N1 84.8(3) . . ? O1' Cu1 O1 77.1(2) . 4_565 ? O3 Cu1 O1 98.8(2) . 4_565 ? O2 Cu1 O1 87.7(2) . 4_565 ? N1 Cu1 O1 93.1(2) . 4_565 ? O1' Cu1 O5' 96.3(2) . . ? O3 Cu1 O5' 91.5(2) . . ? O2 Cu1 O5' 83.3(2) . . ? N1 Cu1 O5' 93.1(2) . . ? O1 Cu1 O5' 168.6(2) 4_565 . ? O1 Cu1' O3' 96.4(2) 4_565 . ? O1 Cu1' O1' 86.8(2) 4_565 . ? O3' Cu1' O1' 171.0(3) . . ? O1 Cu1' N1' 175.7(3) 4_565 . ? O3' Cu1' N1' 81.9(3) . . ? O1' Cu1' N1' 94.3(3) . . ? O1 Cu1' O2' 103.5(2) 4_565 . ? O3' Cu1' O2' 97.7(2) . . ? O1' Cu1' O2' 89.7(2) . . ? N1' Cu1' O2' 80.7(2) . . ? O4W Na1 O3 79.5(4) . . ? O4W Na1 O2' 171.6(4) . . ? O3 Na1 O2' 98.0(2) . . ? O4W Na1 O6' 94.6(4) . . ? O3 Na1 O6' 132.8(3) . . ? O2' Na1 O6' 81.1(2) . . ? O4W Na1 O6W 115.9(5) . . ? O3 Na1 O6W 73.9(3) . . ? O2' Na1 O6W 70.7(3) . . ? O6' Na1 O6W 144.4(3) . . ? O4W Na1 O5W 103.7(5) . . ? O3 Na1 O5W 140.8(3) . . ? O2' Na1 O5W 83.4(4) . . ? O6' Na1 O5W 86.2(3) . . ? O6W Na1 O5W 69.7(4) . . ? O4W Na1 K1 132.2(3) . . ? O3 Na1 K1 115.8(2) . . ? O2' Na1 K1 56.17(18) . . ? O6' Na1 K1 102.74(19) . . ? O6W Na1 K1 43.2(3) . . ? O5W Na1 K1 35.6(3) . . ? O7W K1 O5W 115.9(6) . . ? O7W K1 O5 74.1(5) . . ? O5W K1 O5 168.4(5) . . ? O7W K1 O9W 110.2(5) . . ? O5W K1 O9W 61.0(4) . . ? O5 K1 O9W 122.7(4) . . ? O7W K1 O6W 36.9(5) . . ? O5W K1 O6W 79.1(6) . . ? O5 K1 O6W 110.5(5) . . ? O9W K1 O6W 94.7(4) . . ? O7W K1 O8W 66.8(5) . . ? O5W K1 O8W 107.6(4) . . ? O5 K1 O8W 81.3(3) . . ? O9W K1 O8W 53.6(3) . . ? O6W K1 O8W 78.6(4) . . ? O7W K1 O10W 137.2(5) . . ? O5W K1 O10W 85.2(4) . . ? O5 K1 O10W 90.8(3) . . ? O9W K1 O10W 46.0(3) . . ? O6W K1 O10W 140.0(4) . . ? O8W K1 O10W 71.5(3) . . ? O7W K1 O4W 127.2(5) . 1_655 ? O5W K1 O4W 115.0(5) . 1_655 ? O5 K1 O4W 53.9(3) . 1_655 ? O9W K1 O4W 105.8(4) . 1_655 ? O6W K1 O4W 158.9(5) . 1_655 ? O8W K1 O4W 109.6(3) . 1_655 ? O10W K1 O4W 59.9(3) . 1_655 ? O7W K1 O6 139.6(5) . . ? O5W K1 O6 70.9(4) . . ? O5 K1 O6 97.7(3) . . ? O9W K1 O6 107.4(3) . . ? O6W K1 O6 126.2(4) . . ? O8W K1 O6 152.6(3) . . ? O10W K1 O6 81.1(3) . . ? O4W K1 O6 52.2(3) 1_655 . ? O7W K1 O2' 72.2(5) . . ? O5W K1 O2' 79.6(3) . . ? O5 K1 O2' 99.1(3) . . ? O9W K1 O2' 137.7(3) . . ? O6W K1 O2' 61.1(3) . . ? O8W K1 O2' 137.2(3) . . ? O10W K1 O2' 150.6(3) . . ? O4W K1 O2' 104.4(3) 1_655 . ? O6 K1 O2' 70.1(2) . . ? O7W K1 Na1 76.7(4) . . ? O5W K1 Na1 46.5(3) . . ? O5 K1 Na1 137.0(3) . . ? O9W K1 Na1 96.7(3) . . ? O6W K1 Na1 43.6(3) . . ? O8W K1 Na1 114.7(2) . . ? O10W K1 Na1 131.7(3) . . ? O4W K1 Na1 135.4(3) 1_655 . ? O6 K1 Na1 84.71(19) . . ? O2' K1 Na1 41.40(14) . . ? C4' O6' Na1 159.7(5) . . ? C11 O3 Cu1 113.8(6) . . ? C11 O3 Na1 123.3(6) . . ? Cu1 O3 Na1 120.5(3) . . ? C11' O5' Cu1 140.1(6) . . ? C1 O1 Cu1' 128.8(5) . 4_666 ? C1 O1 Cu1 108.0(5) . 4_666 ? Cu1' O1 Cu1 91.4(2) 4_666 4_666 ? C11' O3' Cu1' 113.7(5) 1_655 . ? C9' O2' Cu1' 110.0(6) . . ? C9' O2' Na1 122.7(6) . . ? Cu1' O2' Na1 115.6(3) . . ? C9' O2' K1 111.9(5) . . ? Cu1' O2' K1 110.8(2) . . ? Na1 O2' K1 82.4(2) . . ? C4 O6 K1 124.0(6) . . ? C9 O2 Cu1 113.4(6) . . ? C8' N1' C10' 110.0(6) . . ? C8' N1' C7' 111.7(7) . . ? C10' N1' C7' 110.8(6) . . ? C8' N1' Cu1' 110.5(5) . . ? C10' N1' Cu1' 103.2(5) . . ? C7' N1' Cu1' 110.3(5) . . ? C10 N1 C8 115.9(7) . . ? C10 N1 C7 108.4(7) . . ? C8 N1 C7 111.8(7) . . ? C10 N1 Cu1 105.4(5) . . ? C8 N1 Cu1 105.5(6) . . ? C7 N1 Cu1 109.4(5) . . ? C5' C4' O6' 118.7(8) . . ? C5' C4' C3' 120.0(8) . . ? O6' C4' C3' 121.3(7) . . ? C1' O1' Cu1 129.9(5) . . ? C1' O1' Cu1' 119.2(5) . . ? Cu1 O1' Cu1' 104.4(3) . . ? C6 C5 C4 121.8(8) . . ? C11 O5 K1 151.9(7) 1_655 . ? C1' C2' C3' 121.6(8) 3_667 . ? O5' C11' O3' 124.7(8) . 1_455 ? O5' C11' C10' 118.7(8) . 1_455 ? O3' C11' C10' 116.5(7) 1_455 1_455 ? C2' C3' C4' 119.4(8) . . ? C1' C6' C5' 119.9(7) 3_667 . ? C1' C6' C7' 120.3(7) 3_667 3_667 ? C5' C6' C7' 119.8(8) . 3_667 ? N1' C10' C11' 109.5(7) . 1_655 ? O6 C4 C3 119.8(8) . . ? O6 C4 C5 121.9(8) . . ? C3 C4 C5 118.3(8) . . ? C5 C6 C1 120.3(8) . . ? C5 C6 C7 119.2(8) . 4_666 ? C1 C6 C7 120.5(8) . 4_666 ? C6 C7 N1 113.8(7) 4_565 . ? C4 C3 C2 120.9(8) . . ? C1 C2 C3 120.7(8) . . ? C4' C5' C6' 120.5(8) . . ? O1 C1 C6 118.8(7) . . ? O1 C1 C2 123.2(8) . . ? C6 C1 C2 118.0(8) . . ? N1 C8 C9 111.3(7) . . ? C6' C7' N1' 110.6(7) 3_667 . ? N1 C10 C11 110.2(8) . . ? O4 C9 O2 122.9(9) . . ? O4 C9 C8 120.5(8) . . ? O2 C9 C8 116.6(8) . . ? O5 C11 O3 124.7(11) 1_455 . ? O5 C11 C10 118.5(10) 1_455 . ? O3 C11 C10 116.8(8) . . ? O1' C1' C2' 121.8(8) . 3_667 ? O1' C1' C6' 119.5(7) . 3_667 ? C2' C1' C6' 118.7(8) 3_667 3_667 ? Na1 O4W K1 141.9(5) . 1_455 ? K1 O5W Na1 97.9(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.542 _refine_diff_density_min -1.412 _refine_diff_density_rms 0.195