# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_lj-4 _database_code_depnum_ccdc_archive 'CCDC 889597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 Cu3 N4 O12' _chemical_formula_weight 821.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3526(10) _cell_length_b 8.6543(10) _cell_length_c 10.7547(13) _cell_angle_alpha 85.213(2) _cell_angle_beta 75.719(2) _cell_angle_gamma 80.446(2) _cell_volume 742.20(15) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3373 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 413 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.650 _exptl_absorpt_correction_T_max 0.718 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3804 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2586 _reflns_number_gt 2399 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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. The atom N2 clearly appears to be disordered over two sites. We have tried the disorder refinement, but we have found that the model gets worse. ; _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^)+(0.0504P)^2^+1.0983P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2586 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.0000 0.02162(15) Uani 1 2 d S . . O1 O 0.5324(3) 0.0670(3) 0.1586(2) 0.0374(6) Uani 1 1 d . . . N1 N 1.0588(3) 0.2637(3) -0.0290(2) 0.0181(5) Uani 1 1 d . . . C1 C 0.6338(3) 0.1474(3) 0.1788(3) 0.0214(6) Uani 1 1 d . . . Cu2 Cu 0.87700(4) 0.15346(4) -0.06951(3) 0.01803(13) Uani 1 1 d . . . O2 O 0.7314(3) 0.2227(2) 0.09636(19) 0.0267(5) Uani 1 1 d . . . C2 C 0.6333(4) 0.1587(3) 0.3172(3) 0.0234(6) Uani 1 1 d . . . N2 N 1.0431(6) 0.4252(4) 0.3369(3) 0.0763(15) Uani 1 1 d . . . H2A H 1.0478 0.3250 0.3399 0.092 Uiso 1 1 calc R A 1 O3 O 0.9422(2) -0.0390(2) 0.1974(2) 0.0273(5) Uani 1 1 d . . . C3 C 0.4827(4) 0.2101(5) 0.4022(3) 0.0440(9) Uani 1 1 d . . . H3A H 0.3846 0.2302 0.3736 0.053 Uiso 1 1 calc R . . O4 O 1.0733(3) 0.0933(2) 0.3016(2) 0.0266(5) Uani 1 1 d . . . C4 C 0.4782(5) 0.2316(6) 0.5292(4) 0.0572(12) Uani 1 1 d . . . H4A H 0.3772 0.2688 0.5848 0.069 Uiso 1 1 calc R . . O5 O 1.1568(3) 0.6302(3) 0.2293(2) 0.0376(6) Uani 1 1 d . . . C5 C 0.6203(5) 0.1988(5) 0.5738(3) 0.0475(10) Uani 1 1 d . . . H5A H 0.6157 0.2122 0.6596 0.057 Uiso 1 1 calc R . . O6 O 0.7071(3) 0.0525(3) -0.0981(2) 0.0308(5) Uani 1 1 d . . . C6 C 0.7700(4) 0.1460(4) 0.4915(3) 0.0299(7) Uani 1 1 d . . . H6A H 0.8667 0.1244 0.5220 0.036 Uiso 1 1 calc R . . C7 C 0.7788(4) 0.1242(3) 0.3625(3) 0.0199(6) Uani 1 1 d . . . C8 C 0.9459(3) 0.0558(3) 0.2812(3) 0.0178(6) Uani 1 1 d . . . C9 C 1.2060(4) 0.2695(4) -0.1142(3) 0.0267(7) Uani 1 1 d . . . H9A H 1.2254 0.2212 -0.1917 0.032 Uiso 1 1 calc R . . C10 C 1.0353(3) 0.3347(3) 0.0823(3) 0.0178(5) Uani 1 1 d . . . H10A H 0.9349 0.3313 0.1430 0.021 Uiso 1 1 calc R . . C11 C 1.1520(4) 0.4119(3) 0.1109(3) 0.0210(6) Uani 1 1 d . . . C12 C 1.1188(4) 0.4985(4) 0.2325(3) 0.0290(7) Uani 1 1 d . . . C13 C 0.9457(7) 0.5208(7) 0.4539(5) 0.0306(10) Uani 0.585(6) 1 d P . 1 H13A H 0.9329 0.6325 0.4317 0.037 Uiso 0.585(6) 1 calc PR . 1 H13B H 0.8363 0.4902 0.4885 0.037 Uiso 0.585(6) 1 calc PR . 1 C13' C 1.0819(10) 0.4533(10) 0.4707(8) 0.0306(10) Uani 0.415(6) 1 d P . 2 H13E H 1.1041 0.3559 0.5193 0.037 Uiso 0.415(6) 1 calc PR . 2 H13F H 1.1738 0.5125 0.4598 0.037 Uiso 0.415(6) 1 calc PR . 2 C17 C 1.3016(4) 0.4180(4) 0.0216(3) 0.0340(8) Uani 1 1 d . . . H17A H 1.3821 0.4711 0.0374 0.041 Uiso 1 1 calc R . . C18 C 1.3285(4) 0.3431(4) -0.0920(3) 0.0391(9) Uani 1 1 d . . . H18A H 1.4292 0.3428 -0.1530 0.047 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 Cu1 0.0166(3) 0.0322(3) 0.0185(3) -0.0054(2) -0.00420(19) -0.0084(2) O1 0.0298(12) 0.0653(16) 0.0243(11) -0.0095(11) -0.0042(10) -0.0276(11) N1 0.0193(12) 0.0190(11) 0.0165(11) -0.0043(9) -0.0037(9) -0.0032(9) C1 0.0133(13) 0.0299(15) 0.0221(14) -0.0072(12) -0.0042(11) -0.0032(11) Cu2 0.01467(19) 0.0233(2) 0.0178(2) -0.00938(14) -0.00333(14) -0.00415(13) O2 0.0278(11) 0.0337(11) 0.0198(10) -0.0091(9) -0.0001(9) -0.0129(9) C2 0.0203(14) 0.0305(15) 0.0192(14) -0.0064(12) -0.0021(11) -0.0041(12) N2 0.155(4) 0.059(2) 0.0204(16) -0.0196(15) 0.011(2) -0.071(3) O3 0.0188(10) 0.0306(11) 0.0338(12) -0.0213(9) -0.0019(9) -0.0042(8) C3 0.0218(17) 0.077(3) 0.0296(18) -0.0112(18) -0.0038(14) 0.0048(17) O4 0.0223(11) 0.0357(12) 0.0251(11) -0.0126(9) -0.0072(9) -0.0056(9) C4 0.033(2) 0.101(4) 0.0248(19) -0.021(2) 0.0044(16) 0.016(2) O5 0.0583(16) 0.0296(12) 0.0337(13) -0.0081(10) -0.0175(12) -0.0187(11) C5 0.046(2) 0.075(3) 0.0158(16) -0.0150(16) -0.0038(15) 0.0100(19) O6 0.0177(10) 0.0499(14) 0.0275(11) -0.0191(10) 0.0012(9) -0.0140(9) C6 0.0309(17) 0.0384(18) 0.0197(15) -0.0064(13) -0.0088(13) 0.0036(14) C7 0.0216(14) 0.0202(13) 0.0176(13) -0.0057(11) -0.0028(11) -0.0028(11) C8 0.0201(14) 0.0171(13) 0.0170(13) -0.0026(10) -0.0055(11) -0.0026(10) C9 0.0300(16) 0.0274(15) 0.0222(15) -0.0124(12) 0.0007(13) -0.0081(13) C10 0.0188(13) 0.0189(13) 0.0163(13) -0.0037(10) -0.0040(11) -0.0031(10) C11 0.0256(15) 0.0203(13) 0.0194(14) -0.0051(11) -0.0076(12) -0.0045(11) C12 0.0369(18) 0.0306(16) 0.0243(16) -0.0112(13) -0.0082(13) -0.0125(13) C13 0.037(3) 0.035(3) 0.021(3) -0.012(2) -0.008(3) 0.000(2) C13' 0.037(3) 0.035(3) 0.021(3) -0.012(2) -0.008(3) 0.000(2) C17 0.0267(17) 0.0421(19) 0.0378(19) -0.0159(15) -0.0029(15) -0.0188(15) C18 0.0288(17) 0.048(2) 0.0364(19) -0.0199(16) 0.0133(14) -0.0169(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 Cu1 O6 1.895(2) 2_655 ? Cu1 O6 1.895(2) . ? Cu1 O1 1.940(2) . ? Cu1 O1 1.940(2) 2_655 ? O1 C1 1.249(4) . ? N1 C9 1.346(4) . ? N1 C10 1.348(3) . ? N1 Cu2 2.069(2) . ? C1 O2 1.264(4) . ? C1 C2 1.500(4) . ? Cu2 O6 1.882(2) . ? Cu2 O3 1.965(2) 2_755 ? Cu2 O2 1.972(2) . ? C2 C3 1.389(4) . ? C2 C7 1.396(4) . ? N2 C12 1.315(5) . ? N2 C13 1.541(6) . ? N2 C13' 1.597(9) . ? N2 H2A 0.8600 . ? O3 C8 1.277(3) . ? O3 Cu2 1.965(2) 2_755 ? C3 C4 1.384(5) . ? C3 H3A 0.9300 . ? O4 C8 1.236(3) . ? C4 C5 1.367(6) . ? C4 H4A 0.9300 . ? O5 C12 1.228(4) . ? C5 C6 1.374(5) . ? C5 H5A 0.9300 . ? C6 C7 1.399(4) . ? C6 H6A 0.9300 . ? C7 C8 1.508(4) . ? C9 C18 1.367(5) . ? C9 H9A 0.9300 . ? C10 C11 1.375(4) . ? C10 H10A 0.9300 . ? C11 C17 1.381(4) . ? C11 C12 1.505(4) . ? C13 C13 1.487(11) 2_766 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13' C13' 1.488(16) 2_766 ? C13' H13E 0.9700 . ? C13' H13F 0.9700 . ? C17 C18 1.383(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? 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 O6 Cu1 O6 180.0 2_655 . ? O6 Cu1 O1 86.74(9) 2_655 . ? O6 Cu1 O1 93.26(9) . . ? O6 Cu1 O1 93.26(9) 2_655 2_655 ? O6 Cu1 O1 86.74(9) . 2_655 ? O1 Cu1 O1 179.999(1) . 2_655 ? C1 O1 Cu1 131.2(2) . . ? C9 N1 C10 116.8(2) . . ? C9 N1 Cu2 121.19(19) . . ? C10 N1 Cu2 122.02(18) . . ? O1 C1 O2 127.3(3) . . ? O1 C1 C2 115.3(3) . . ? O2 C1 C2 117.4(2) . . ? O6 Cu2 O3 95.40(9) . 2_755 ? O6 Cu2 O2 89.81(9) . . ? O3 Cu2 O2 161.49(10) 2_755 . ? O6 Cu2 N1 177.33(9) . . ? O3 Cu2 N1 86.62(8) 2_755 . ? O2 Cu2 N1 87.73(9) . . ? C1 O2 Cu2 128.59(19) . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 118.3(3) . . ? C7 C2 C1 122.5(2) . . ? C12 N2 C13 119.3(4) . . ? C12 N2 C13' 118.7(4) . . ? C13 N2 C13' 46.4(3) . . ? C12 N2 H2A 120.4 . . ? C13 N2 H2A 120.4 . . ? C13' N2 H2A 101.9 . . ? C8 O3 Cu2 131.06(18) . 2_755 ? C4 C3 C2 120.3(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? Cu2 O6 Cu1 136.37(12) . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C2 C7 C6 119.2(3) . . ? C2 C7 C8 123.5(2) . . ? C6 C7 C8 117.2(3) . . ? O4 C8 O3 125.7(3) . . ? O4 C8 C7 118.3(2) . . ? O3 C8 C7 116.0(2) . . ? N1 C9 C18 123.1(3) . . ? N1 C9 H9A 118.5 . . ? C18 C9 H9A 118.5 . . ? N1 C10 C11 123.4(3) . . ? N1 C10 H10A 118.3 . . ? C11 C10 H10A 118.3 . . ? C10 C11 C17 118.9(3) . . ? C10 C11 C12 122.4(3) . . ? C17 C11 C12 118.6(3) . . ? O5 C12 N2 124.4(3) . . ? O5 C12 C11 120.4(3) . . ? N2 C12 C11 115.1(3) . . ? C13 C13 N2 102.6(5) 2_766 . ? C13 C13 H13A 111.3 2_766 . ? N2 C13 H13A 111.3 . . ? C13 C13 H13B 111.3 2_766 . ? N2 C13 H13B 111.3 . . ? H13A C13 H13B 109.2 . . ? C13' C13' N2 97.8(8) 2_766 . ? C13' C13' H13E 112.2 2_766 . ? N2 C13' H13E 112.2 . . ? C13' C13' H13F 112.2 2_766 . ? N2 C13' H13F 112.2 . . ? H13E C13' H13F 109.8 . . ? C11 C17 C18 118.3(3) . . ? C11 C17 H17A 120.9 . . ? C18 C17 H17A 120.9 . . ? C9 C18 C17 119.6(3) . . ? C9 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 Cu1 O1 C1 -165.8(3) 2_655 . . . ? O6 Cu1 O1 C1 14.1(3) . . . . ? O1 Cu1 O1 C1 35(7) 2_655 . . . ? Cu1 O1 C1 O2 9.3(5) . . . . ? Cu1 O1 C1 C2 -173.1(2) . . . . ? C9 N1 Cu2 O6 160.4(19) . . . . ? C10 N1 Cu2 O6 -21(2) . . . . ? C9 N1 Cu2 O3 21.0(2) . . . 2_755 ? C10 N1 Cu2 O3 -159.9(2) . . . 2_755 ? C9 N1 Cu2 O2 -176.7(2) . . . . ? C10 N1 Cu2 O2 2.5(2) . . . . ? O1 C1 O2 Cu2 -45.7(4) . . . . ? C2 C1 O2 Cu2 136.6(2) . . . . ? O6 Cu2 O2 C1 40.0(3) . . . . ? O3 Cu2 O2 C1 -66.6(4) 2_755 . . . ? N1 Cu2 O2 C1 -138.9(3) . . . . ? O1 C1 C2 C3 -54.2(4) . . . . ? O2 C1 C2 C3 123.7(3) . . . . ? O1 C1 C2 C7 127.8(3) . . . . ? O2 C1 C2 C7 -54.3(4) . . . . ? C7 C2 C3 C4 2.0(6) . . . . ? C1 C2 C3 C4 -176.0(4) . . . . ? C2 C3 C4 C5 -1.7(7) . . . . ? C3 C4 C5 C6 0.9(8) . . . . ? O3 Cu2 O6 Cu1 151.29(19) 2_755 . . . ? O2 Cu2 O6 Cu1 -10.9(2) . . . . ? N1 Cu2 O6 Cu1 12(2) . . . . ? O6 Cu1 O6 Cu2 63(15) 2_655 . . . ? O1 Cu1 O6 Cu2 -6.7(2) . . . . ? O1 Cu1 O6 Cu2 173.3(2) 2_655 . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C3 C2 C7 C6 -1.5(5) . . . . ? C1 C2 C7 C6 176.4(3) . . . . ? C3 C2 C7 C8 175.1(3) . . . . ? C1 C2 C7 C8 -7.0(4) . . . . ? C5 C6 C7 C2 0.7(5) . . . . ? C5 C6 C7 C8 -176.0(3) . . . . ? Cu2 O3 C8 O4 -2.1(4) 2_755 . . . ? Cu2 O3 C8 C7 178.95(19) 2_755 . . . ? C2 C7 C8 O4 147.2(3) . . . . ? C6 C7 C8 O4 -36.1(4) . . . . ? C2 C7 C8 O3 -33.7(4) . . . . ? C6 C7 C8 O3 142.9(3) . . . . ? C10 N1 C9 C18 -0.1(5) . . . . ? Cu2 N1 C9 C18 179.0(3) . . . . ? C9 N1 C10 C11 0.7(4) . . . . ? Cu2 N1 C10 C11 -178.5(2) . . . . ? N1 C10 C11 C17 0.1(4) . . . . ? N1 C10 C11 C12 176.2(3) . . . . ? C13 N2 C12 O5 20.2(7) . . . . ? C13' N2 C12 O5 -33.4(7) . . . . ? C13 N2 C12 C11 -157.4(4) . . . . ? C13' N2 C12 C11 149.0(4) . . . . ? C10 C11 C12 O5 -134.7(3) . . . . ? C17 C11 C12 O5 41.5(5) . . . . ? C10 C11 C12 N2 43.0(5) . . . . ? C17 C11 C12 N2 -140.9(4) . . . . ? C12 N2 C13 C13 -108.0(6) . . . 2_766 ? C13' N2 C13 C13 -4.9(6) . . . 2_766 ? C12 N2 C13' C13' 109.2(8) . . . 2_766 ? C13 N2 C13' C13' 4.8(5) . . . 2_766 ? C10 C11 C17 C18 -1.3(5) . . . . ? C12 C11 C17 C18 -177.6(3) . . . . ? N1 C9 C18 C17 -1.1(6) . . . . ? C11 C17 C18 C9 1.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.744 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.088 data_lj-1 _database_code_depnum_ccdc_archive 'CCDC 889598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 Cu N5 O12' _chemical_formula_weight 615.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0931(6) _cell_length_b 13.8662(10) _cell_length_c 20.4468(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.7390(10) _cell_angle_gamma 90.00 _cell_volume 2575.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3263 _cell_measurement_theta_min 1.78 _cell_measurement_theta_max 26.00 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 0.922 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8371 _exptl_absorpt_correction_T_max 0.8665 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14512 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5046 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0563P)^2^+0.5227P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5046 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.09185(4) 0.19175(2) 0.244109(16) 0.02953(12) Uani 1 1 d . . . O1 O 0.1235(2) 0.11003(13) 0.16682(9) 0.0323(5) Uani 1 1 d . . . N1 N 0.3238(4) 0.0613(2) 0.03901(18) 0.0632(9) Uani 1 1 d . . . C1 C 0.1942(3) 0.0310(2) 0.16801(14) 0.0343(7) Uani 1 1 d . . . O1W O 0.0145(2) 0.31650(15) 0.16487(11) 0.0457(6) Uani 1 1 d . . . H1WA H -0.0714 0.3109 0.1469 0.055 Uiso 1 1 d R . . H1WB H 0.0265 0.3580 0.1952 0.055 Uiso 1 1 d R . . O2 O 0.2811(3) 0.00322(19) 0.21155(13) 0.0725(9) Uani 1 1 d . . . N2 N 0.2997(2) 0.24231(16) 0.24862(11) 0.0301(5) Uani 1 1 d . . . C2 C 0.1587(3) -0.0333(2) 0.10897(14) 0.0312(6) Uani 1 1 d . . . O2W O 0.2012(3) 0.0488(2) 0.34048(13) 0.0729(8) Uani 1 1 d . . . H2WA H 0.2052 0.0126 0.3070 0.087 Uiso 1 1 d R . . H2WB H 0.2827 0.0789 0.3434 0.087 Uiso 1 1 d R . . O3 O 0.4002(4) 0.0857(2) 0.08719(17) 0.0900(11) Uani 1 1 d . . . O3W O 0.1939(3) 0.3385(3) 0.05990(15) 0.1050(13) Uani 1 1 d . . . H3WA H 0.1475 0.3252 0.0939 0.126 Uiso 1 1 d R . . H3WB H 0.1309 0.3539 0.0297 0.126 Uiso 1 1 d R . . N3 N 0.5106(3) 0.30927(19) 0.07526(13) 0.0439(7) Uani 1 1 d . . . H3A H 0.4182 0.3203 0.0786 0.053 Uiso 1 1 calc R . . C3 C 0.2152(3) -0.0165(2) 0.04732(15) 0.0404(7) Uani 1 1 d . . . O4 O 0.3403(5) 0.0923(3) -0.01511(19) 0.1376(18) Uani 1 1 d . . . N4 N -0.1069(2) 0.12693(17) 0.25082(11) 0.0298(5) Uani 1 1 d . . . C4 C 0.1784(4) -0.0709(3) -0.00757(16) 0.0566(10) Uani 1 1 d . . . H4A H 0.2192 -0.0571 -0.0474 0.068 Uiso 1 1 calc R . . O4W O 0.0382(2) 0.42791(19) -0.04865(12) 0.0608(7) Uani 1 1 d . . . H4WA H 0.0133 0.4337 -0.0891 0.073 Uiso 1 1 d R . . H4WB H 0.1300 0.4391 -0.0441 0.073 Uiso 1 1 d R . . O5 O -0.0451(2) -0.22907(14) 0.17927(10) 0.0369(5) Uani 1 1 d . . . N5 N -0.2832(3) 0.09372(19) 0.43573(12) 0.0418(6) Uani 1 1 d . . . H5B H -0.1912 0.1040 0.4305 0.050 Uiso 1 1 calc R . . C5 C 0.0807(5) -0.1456(3) -0.00251(17) 0.0624(11) Uani 1 1 d . . . H5A H 0.0515 -0.1815 -0.0393 0.075 Uiso 1 1 calc R . . O6 O -0.0010(4) -0.08459(16) 0.22307(12) 0.0701(9) Uani 1 1 d . . . C6 C 0.0260(4) -0.1673(2) 0.05756(15) 0.0443(8) Uani 1 1 d . . . H6A H -0.0373 -0.2195 0.0611 0.053 Uiso 1 1 calc R . . O7 O 0.7268(2) 0.2773(2) 0.12739(13) 0.0598(7) Uani 1 1 d . . . C7 C 0.0633(3) -0.1128(2) 0.11283(13) 0.0296(6) Uani 1 1 d . . . O8 O -0.5028(2) 0.0576(2) 0.38718(12) 0.0601(7) Uani 1 1 d . . . C8 C 0.0009(3) -0.1428(2) 0.17774(14) 0.0330(7) Uani 1 1 d . . . C9 C 0.3717(3) 0.2509(2) 0.19326(14) 0.0312(6) Uani 1 1 d . . . H9A H 0.3230 0.2339 0.1539 0.037 Uiso 1 1 calc R . . C10 C 0.5147(3) 0.2838(2) 0.19195(15) 0.0340(7) Uani 1 1 d . . . C11 C 0.5932(3) 0.2906(2) 0.12896(16) 0.0390(7) Uani 1 1 d . . . C12 C 0.5719(4) 0.3117(3) 0.01067(16) 0.0488(9) Uani 1 1 d . . . H12A H 0.4924 0.3094 -0.0227 0.059 Uiso 1 1 calc R . . H12B H 0.6334 0.2553 0.0053 0.059 Uiso 1 1 calc R . . C13 C 0.5880(3) 0.3073(2) 0.25068(16) 0.0418(8) Uani 1 1 d . . . H13A H 0.6854 0.3280 0.2516 0.050 Uiso 1 1 calc R . . C14 C 0.5148(4) 0.2997(2) 0.30740(16) 0.0446(8) Uani 1 1 d . . . H14A H 0.5617 0.3163 0.3472 0.053 Uiso 1 1 calc R . . C15 C 0.3710(3) 0.2674(2) 0.30521(15) 0.0383(7) Uani 1 1 d . . . H15A H 0.3221 0.2629 0.3440 0.046 Uiso 1 1 calc R . . C16 C -0.1678(3) 0.1191(2) 0.30919(14) 0.0322(6) Uani 1 1 d . . . H16A H -0.1162 0.1438 0.3458 0.039 Uiso 1 1 calc R . . C17 C -0.3022(3) 0.0766(2) 0.31789(14) 0.0329(7) Uani 1 1 d . . . C18 C -0.3707(3) 0.0742(2) 0.38335(15) 0.0371(7) Uani 1 1 d . . . C19 C -0.3374(4) 0.0982(2) 0.50146(15) 0.0424(8) Uani 1 1 d . . . H19A H -0.2547 0.0977 0.5332 0.051 Uiso 1 1 calc R . . H19B H -0.3973 0.0418 0.5091 0.051 Uiso 1 1 calc R . . C20 C -0.3807(3) 0.0415(2) 0.26279(16) 0.0406(8) Uani 1 1 d . . . H20A H -0.4733 0.0142 0.2665 0.049 Uiso 1 1 calc R . . C21 C -0.3194(3) 0.0479(3) 0.20306(16) 0.0452(8) Uani 1 1 d . . . H21A H -0.3690 0.0234 0.1658 0.054 Uiso 1 1 calc R . . C22 C -0.1830(3) 0.0910(2) 0.19852(14) 0.0367(7) Uani 1 1 d . . . H22A H -0.1425 0.0952 0.1577 0.044 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 Cu1 0.0271(2) 0.0310(2) 0.0312(2) -0.00567(15) 0.00917(14) -0.00431(15) O1 0.0340(11) 0.0316(11) 0.0320(11) -0.0050(9) 0.0094(9) -0.0006(9) N1 0.063(2) 0.065(2) 0.064(2) -0.0009(18) 0.0242(18) -0.0216(17) C1 0.0350(17) 0.0334(16) 0.0342(17) -0.0039(13) -0.0020(13) 0.0026(13) O1W 0.0396(13) 0.0532(14) 0.0442(13) -0.0075(11) 0.0012(10) 0.0045(10) O2 0.087(2) 0.0595(16) 0.0671(18) -0.0181(14) -0.0405(16) 0.0217(15) N2 0.0297(13) 0.0305(13) 0.0304(13) -0.0027(10) 0.0040(10) -0.0028(10) C2 0.0329(16) 0.0292(15) 0.0316(16) 0.0011(12) 0.0033(12) 0.0074(12) O2W 0.0518(17) 0.095(2) 0.0726(19) -0.0189(17) 0.0145(14) -0.0111(15) O3 0.083(2) 0.097(2) 0.092(2) -0.0271(19) 0.0328(19) -0.0467(19) O3W 0.0496(18) 0.202(4) 0.0640(19) 0.052(2) 0.0085(14) 0.012(2) N3 0.0292(14) 0.0604(18) 0.0431(16) 0.0069(14) 0.0115(12) -0.0037(13) C3 0.0459(19) 0.0347(17) 0.0417(19) 0.0007(14) 0.0137(15) -0.0056(14) O4 0.164(4) 0.151(4) 0.098(3) 0.049(3) 0.017(3) -0.093(3) N4 0.0260(13) 0.0357(13) 0.0280(13) -0.0001(10) 0.0030(10) 0.0006(10) C4 0.083(3) 0.057(2) 0.0316(19) -0.0019(16) 0.0219(18) -0.010(2) O4W 0.0398(14) 0.0851(19) 0.0574(16) -0.0079(14) 0.0003(12) -0.0064(13) O5 0.0407(12) 0.0344(11) 0.0363(12) 0.0049(9) 0.0089(9) -0.0038(9) N5 0.0309(14) 0.0608(18) 0.0349(15) -0.0029(13) 0.0126(12) -0.0014(12) C5 0.100(3) 0.054(2) 0.033(2) -0.0161(17) 0.007(2) -0.014(2) O6 0.139(3) 0.0355(13) 0.0384(14) -0.0034(11) 0.0365(15) -0.0030(15) C6 0.063(2) 0.0375(17) 0.0334(17) -0.0048(14) 0.0069(15) -0.0102(16) O7 0.0293(13) 0.0867(19) 0.0644(17) 0.0118(14) 0.0107(11) 0.0020(12) C7 0.0331(16) 0.0300(14) 0.0262(15) 0.0005(12) 0.0056(12) 0.0047(12) O8 0.0319(13) 0.095(2) 0.0539(15) 0.0048(14) 0.0121(11) -0.0211(13) C8 0.0371(17) 0.0315(16) 0.0310(16) 0.0050(13) 0.0071(13) 0.0061(13) C9 0.0290(16) 0.0337(16) 0.0310(16) 0.0008(12) 0.0029(12) -0.0045(12) C10 0.0311(16) 0.0291(15) 0.0419(18) 0.0032(13) 0.0037(13) -0.0031(12) C11 0.0311(18) 0.0384(18) 0.048(2) 0.0018(14) 0.0095(15) -0.0051(13) C12 0.048(2) 0.060(2) 0.0403(19) -0.0038(17) 0.0160(15) -0.0123(17) C13 0.0328(17) 0.0413(18) 0.051(2) 0.0000(16) 0.0009(15) -0.0079(14) C14 0.0427(19) 0.0471(19) 0.0426(19) -0.0065(15) -0.0111(15) -0.0056(15) C15 0.0398(18) 0.0417(17) 0.0335(17) -0.0016(14) 0.0030(14) -0.0024(14) C16 0.0306(16) 0.0391(16) 0.0270(15) -0.0025(13) 0.0035(12) -0.0023(13) C17 0.0270(16) 0.0364(16) 0.0357(16) 0.0015(13) 0.0072(12) -0.0032(12) C18 0.0297(17) 0.0411(17) 0.0411(18) 0.0027(14) 0.0081(14) -0.0054(13) C19 0.0368(18) 0.053(2) 0.0383(18) 0.0010(15) 0.0130(14) 0.0013(15) C20 0.0282(17) 0.0464(19) 0.0470(19) -0.0021(15) 0.0008(14) -0.0083(14) C21 0.0369(19) 0.058(2) 0.0400(19) -0.0054(16) -0.0036(15) -0.0089(16) C22 0.0339(17) 0.0469(18) 0.0293(16) -0.0020(13) 0.0016(13) -0.0008(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.976(2) 2 ? Cu1 O1 1.9768(18) . ? Cu1 N2 2.014(2) . ? Cu1 N4 2.029(2) . ? O1 C1 1.270(3) . ? N1 O4 1.203(4) . ? N1 O3 1.226(4) . ? N1 C3 1.478(4) . ? C1 O2 1.224(3) . ? C1 C2 1.523(4) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? N2 C9 1.340(4) . ? N2 C15 1.345(4) . ? C2 C3 1.403(4) . ? C2 C7 1.407(4) . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8500 . ? N3 C11 1.326(4) . ? N3 C12 1.458(4) . ? N3 H3A 0.8600 . ? C3 C4 1.380(4) . ? N4 C22 1.342(4) . ? N4 C16 1.344(3) . ? C4 C5 1.373(5) . ? C4 H4A 0.9300 . ? O4W H4WA 0.8501 . ? O4W H4WB 0.8500 . ? O5 C8 1.269(3) . ? O5 Cu1 1.976(2) 2_545 ? N5 C18 1.331(4) . ? N5 C19 1.455(4) . ? N5 H5B 0.8600 . ? C5 C6 1.380(5) . ? C5 H5A 0.9300 . ? O6 C8 1.230(4) . ? C6 C7 1.388(4) . ? C6 H6A 0.9300 . ? O7 C11 1.231(4) . ? C7 C8 1.526(4) . ? O8 C18 1.229(3) . ? C9 C10 1.379(4) . ? C9 H9A 0.9300 . ? C10 C13 1.385(4) . ? C10 C11 1.505(4) . ? C12 C19 1.514(4) 4_665 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.369(5) . ? C13 H13A 0.9300 . ? C14 C15 1.381(4) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.376(4) . ? C16 H16A 0.9300 . ? C17 C20 1.392(4) . ? C17 C18 1.504(4) . ? C19 C12 1.514(4) 4_466 ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.369(4) . ? C20 H20A 0.9300 . ? C21 C22 1.384(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? 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 O5 Cu1 O1 175.88(8) 2 . ? O5 Cu1 N2 90.42(9) 2 . ? O1 Cu1 N2 93.68(9) . . ? O5 Cu1 N4 88.08(9) 2 . ? O1 Cu1 N4 87.95(9) . . ? N2 Cu1 N4 171.18(9) . . ? C1 O1 Cu1 124.89(18) . . ? O4 N1 O3 123.4(4) . . ? O4 N1 C3 118.7(4) . . ? O3 N1 C3 117.7(3) . . ? O2 C1 O1 126.5(3) . . ? O2 C1 C2 119.8(3) . . ? O1 C1 C2 113.7(2) . . ? H1WA O1W H1WB 117.5 . . ? C9 N2 C15 118.0(2) . . ? C9 N2 Cu1 119.18(18) . . ? C15 N2 Cu1 122.8(2) . . ? C3 C2 C7 115.7(3) . . ? C3 C2 C1 122.8(3) . . ? C7 C2 C1 121.5(3) . . ? H2WA O2W H2WB 106.0 . . ? H3WA O3W H3WB 107.8 . . ? C11 N3 C12 121.9(3) . . ? C11 N3 H3A 119.0 . . ? C12 N3 H3A 119.0 . . ? C4 C3 C2 123.7(3) . . ? C4 C3 N1 116.3(3) . . ? C2 C3 N1 120.0(3) . . ? C22 N4 C16 117.3(2) . . ? C22 N4 Cu1 122.53(19) . . ? C16 N4 Cu1 120.15(18) . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? H4WA O4W H4WB 107.7 . . ? C8 O5 Cu1 128.86(19) . 2_545 ? C18 N5 C19 122.4(3) . . ? C18 N5 H5B 118.8 . . ? C19 N5 H5B 118.8 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C5 C6 C7 121.4(3) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 C8 118.2(3) . . ? C2 C7 C8 121.2(2) . . ? O6 C8 O5 125.7(3) . . ? O6 C8 C7 119.7(3) . . ? O5 C8 C7 114.5(3) . . ? N2 C9 C10 123.0(3) . . ? N2 C9 H9A 118.5 . . ? C10 C9 H9A 118.5 . . ? C9 C10 C13 118.5(3) . . ? C9 C10 C11 121.6(3) . . ? C13 C10 C11 119.9(3) . . ? O7 C11 N3 121.9(3) . . ? O7 C11 C10 121.5(3) . . ? N3 C11 C10 116.6(3) . . ? N3 C12 C19 111.4(3) . 4_665 ? N3 C12 H12A 109.3 . . ? C19 C12 H12A 109.3 4_665 . ? N3 C12 H12B 109.3 . . ? C19 C12 H12B 109.3 4_665 . ? H12A C12 H12B 108.0 . . ? C14 C13 C10 118.9(3) . . ? C14 C13 H13A 120.6 . . ? C10 C13 H13A 120.6 . . ? C13 C14 C15 119.7(3) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? N2 C15 C14 121.9(3) . . ? N2 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? N4 C16 C17 123.8(3) . . ? N4 C16 H16A 118.1 . . ? C17 C16 H16A 118.1 . . ? C16 C17 C20 118.0(3) . . ? C16 C17 C18 122.2(3) . . ? C20 C17 C18 119.6(3) . . ? O8 C18 N5 122.4(3) . . ? O8 C18 C17 120.6(3) . . ? N5 C18 C17 117.0(3) . . ? N5 C19 C12 111.2(3) . 4_466 ? N5 C19 H19A 109.4 . . ? C12 C19 H19A 109.4 4_466 . ? N5 C19 H19B 109.4 . . ? C12 C19 H19B 109.4 4_466 . ? H19A C19 H19B 108.0 . . ? C21 C20 C17 119.0(3) . . ? C21 C20 H20A 120.5 . . ? C17 C20 H20A 120.5 . . ? C20 C21 C22 119.5(3) . . ? C20 C21 H21A 120.3 . . ? C22 C21 H21A 120.3 . . ? N4 C22 C21 122.4(3) . . ? N4 C22 H22A 118.8 . . ? C21 C22 H22A 118.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O1 C1 -111.4(11) 2 . . . ? N2 Cu1 O1 C1 75.1(2) . . . . ? N4 Cu1 O1 C1 -96.2(2) . . . . ? Cu1 O1 C1 O2 -18.0(5) . . . . ? Cu1 O1 C1 C2 160.04(18) . . . . ? O5 Cu1 N2 C9 -149.1(2) 2 . . . ? O1 Cu1 N2 C9 30.4(2) . . . . ? N4 Cu1 N2 C9 130.8(6) . . . . ? O5 Cu1 N2 C15 31.4(2) 2 . . . ? O1 Cu1 N2 C15 -149.0(2) . . . . ? N4 Cu1 N2 C15 -48.6(7) . . . . ? O2 C1 C2 C3 -104.7(4) . . . . ? O1 C1 C2 C3 77.1(4) . . . . ? O2 C1 C2 C7 76.8(4) . . . . ? O1 C1 C2 C7 -101.4(3) . . . . ? C7 C2 C3 C4 2.0(5) . . . . ? C1 C2 C3 C4 -176.5(3) . . . . ? C7 C2 C3 N1 -176.1(3) . . . . ? C1 C2 C3 N1 5.4(4) . . . . ? O4 N1 C3 C4 22.0(6) . . . . ? O3 N1 C3 C4 -152.5(4) . . . . ? O4 N1 C3 C2 -159.8(4) . . . . ? O3 N1 C3 C2 25.7(5) . . . . ? O5 Cu1 N4 C22 150.6(2) 2 . . . ? O1 Cu1 N4 C22 -28.3(2) . . . . ? N2 Cu1 N4 C22 -129.1(6) . . . . ? O5 Cu1 N4 C16 -29.0(2) 2 . . . ? O1 Cu1 N4 C16 152.0(2) . . . . ? N2 Cu1 N4 C16 51.2(7) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? N1 C3 C4 C5 178.5(4) . . . . ? C3 C4 C5 C6 -2.6(6) . . . . ? C4 C5 C6 C7 2.4(6) . . . . ? C5 C6 C7 C2 0.1(5) . . . . ? C5 C6 C7 C8 -178.7(3) . . . . ? C3 C2 C7 C6 -2.2(4) . . . . ? C1 C2 C7 C6 176.4(3) . . . . ? C3 C2 C7 C8 176.5(3) . . . . ? C1 C2 C7 C8 -4.9(4) . . . . ? Cu1 O5 C8 O6 -15.0(5) 2_545 . . . ? Cu1 O5 C8 C7 164.78(18) 2_545 . . . ? C6 C7 C8 O6 -161.3(3) . . . . ? C2 C7 C8 O6 20.0(4) . . . . ? C6 C7 C8 O5 19.0(4) . . . . ? C2 C7 C8 O5 -159.8(3) . . . . ? C15 N2 C9 C10 0.2(4) . . . . ? Cu1 N2 C9 C10 -179.3(2) . . . . ? N2 C9 C10 C13 1.3(4) . . . . ? N2 C9 C10 C11 178.7(3) . . . . ? C12 N3 C11 O7 2.4(5) . . . . ? C12 N3 C11 C10 -176.1(3) . . . . ? C9 C10 C11 O7 -147.1(3) . . . . ? C13 C10 C11 O7 30.3(4) . . . . ? C9 C10 C11 N3 31.4(4) . . . . ? C13 C10 C11 N3 -151.2(3) . . . . ? C11 N3 C12 C19 -73.9(4) . . . 4_665 ? C9 C10 C13 C14 -1.9(4) . . . . ? C11 C10 C13 C14 -179.3(3) . . . . ? C10 C13 C14 C15 1.1(5) . . . . ? C9 N2 C15 C14 -1.0(4) . . . . ? Cu1 N2 C15 C14 178.4(2) . . . . ? C13 C14 C15 N2 0.4(5) . . . . ? C22 N4 C16 C17 0.0(4) . . . . ? Cu1 N4 C16 C17 179.7(2) . . . . ? N4 C16 C17 C20 -1.3(5) . . . . ? N4 C16 C17 C18 -176.4(3) . . . . ? C19 N5 C18 O8 -0.9(5) . . . . ? C19 N5 C18 C17 177.1(3) . . . . ? C16 C17 C18 O8 162.3(3) . . . . ? C20 C17 C18 O8 -12.6(5) . . . . ? C16 C17 C18 N5 -15.7(4) . . . . ? C20 C17 C18 N5 169.4(3) . . . . ? C18 N5 C19 C12 -72.7(4) . . . 4_466 ? C16 C17 C20 C21 2.1(5) . . . . ? C18 C17 C20 C21 177.3(3) . . . . ? C17 C20 C21 C22 -1.6(5) . . . . ? C16 N4 C22 C21 0.5(4) . . . . ? Cu1 N4 C22 C21 -179.2(2) . . . . ? C20 C21 C22 N4 0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.635 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.063 data_lj-3 _database_code_depnum_ccdc_archive 'CCDC 889599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cu N4 O9' _chemical_formula_weight 551.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.004(3) _cell_length_b 10.719(3) _cell_length_c 11.754(3) _cell_angle_alpha 106.938(5) _cell_angle_beta 101.838(5) _cell_angle_gamma 92.317(4) _cell_volume 1173.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2580 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.15 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6230 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4091 _reflns_number_gt 3465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0474P)^2^+0.6069P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4091 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.86523(3) 0.14352(3) 0.51345(3) 0.02314(12) Uani 1 1 d . . . O1 O 0.75960(18) 0.36566(19) 0.5749(2) 0.0376(5) Uani 1 1 d . . . C1 C 0.6619(2) 0.2850(3) 0.5655(2) 0.0244(6) Uani 1 1 d . . . O1W O 0.3947(2) -0.0425(2) 0.2898(2) 0.0531(6) Uani 1 1 d . . . H1WA H 0.4542 0.0223 0.3294 0.064 Uiso 1 1 d R . . H1WB H 0.3634 -0.0699 0.3413 0.064 Uiso 1 1 d R . . O2 O 0.67216(17) 0.16233(18) 0.53986(17) 0.0286(4) Uani 1 1 d . . . N1 N 0.9444(2) 0.1801(2) 0.6953(2) 0.0251(5) Uani 1 1 d . . . C2 C 0.5252(2) 0.3306(2) 0.5836(2) 0.0233(6) Uani 1 1 d . . . O2W O 0.8717(3) 0.6109(3) 0.7324(3) 0.0771(9) Uani 1 1 d . . . H2WA H 0.8359 0.5357 0.6843 0.093 Uiso 1 1 d R . . H2WB H 0.9568 0.6165 0.7334 0.093 Uiso 1 1 d R . . O3 O 0.03962(17) 0.22925(18) 0.50588(17) 0.0288(4) Uani 1 1 d . . . N2 N 1.2377(3) 0.5009(3) 1.0376(2) 0.0451(7) Uani 1 1 d . . . H3B H 1.2606 0.4386 1.0677 0.054 Uiso 1 1 calc R . . C3 C 0.4087(2) 0.2416(2) 0.5511(2) 0.0225(5) Uani 1 1 d . . . H3A H 0.4165 0.1522 0.5230 0.027 Uiso 1 1 calc R . . O3W O 0.7437(4) -0.1582(3) -0.2119(3) 0.0829(10) Uani 1 1 d . . . H3WA H 0.6893 -0.2279 -0.2436 0.099 Uiso 1 1 d R . . H3WB H 0.7953 -0.1551 -0.2607 0.099 Uiso 1 1 d R . . O4 O 1.1056(2) 0.5602(2) 0.8895(2) 0.0491(6) Uani 1 1 d . . . N3 N 0.7944(2) 0.1077(2) 0.3313(2) 0.0271(5) Uani 1 1 d . . . C4 C 0.2803(2) 0.2840(2) 0.5599(2) 0.0217(5) Uani 1 1 d . . . O5 O 0.6197(2) -0.2271(2) -0.0358(2) 0.0488(6) Uani 1 1 d . . . N4 N 0.4983(2) -0.2116(2) 0.1076(2) 0.0363(6) Uani 1 1 d . . . H5A H 0.4793 -0.1639 0.1738 0.044 Uiso 1 1 calc R . . C5 C 0.1554(3) 0.1850(2) 0.5219(2) 0.0222(6) Uani 1 1 d . . . O6 O 0.17299(19) 0.06883(18) 0.50976(19) 0.0364(5) Uani 1 1 d . . . C6 C 0.2706(3) 0.4175(3) 0.6057(3) 0.0309(6) Uani 1 1 d . . . H6A H 0.1854 0.4472 0.6113 0.037 Uiso 1 1 calc R . . C7 C 0.3870(3) 0.5067(3) 0.6430(3) 0.0379(7) Uani 1 1 d . . . H7A H 0.3802 0.5955 0.6768 0.045 Uiso 1 1 calc R . . C8 C 0.5133(3) 0.4641(3) 0.6302(3) 0.0328(7) Uani 1 1 d . . . H8A H 0.5906 0.5247 0.6527 0.039 Uiso 1 1 calc R . . C9 C 1.0093(3) 0.2997(3) 0.7574(2) 0.0260(6) Uani 1 1 d . . . H9A H 1.0126 0.3609 0.7157 0.031 Uiso 1 1 calc R . . C10 C 1.0718(3) 0.3371(3) 0.8803(2) 0.0255(6) Uani 1 1 d . . . C11 C 1.1404(3) 0.4748(3) 0.9366(3) 0.0284(6) Uani 1 1 d . . . C12 C 1.3075(3) 0.6334(3) 1.0995(3) 0.0438(8) Uani 1 1 d . . . H12A H 1.3397 0.6444 1.1859 0.053 Uiso 1 1 calc R . . H12B H 1.2429 0.6970 1.0912 0.053 Uiso 1 1 calc R . . C13 C 1.0641(3) 0.2463(3) 0.9434(3) 0.0309(6) Uani 1 1 d . . . H13A H 1.1044 0.2676 1.0262 0.037 Uiso 1 1 calc R . . C14 C 0.9952(3) 0.1238(3) 0.8796(3) 0.0340(7) Uani 1 1 d . . . H14A H 0.9872 0.0618 0.9198 0.041 Uiso 1 1 calc R . . C15 C 0.9383(3) 0.0933(3) 0.7568(3) 0.0298(6) Uani 1 1 d . . . H15A H 0.8940 0.0096 0.7149 0.036 Uiso 1 1 calc R . . C16 C 0.7114(3) -0.0008(3) 0.2632(2) 0.0270(6) Uani 1 1 d . . . H16A H 0.6789 -0.0558 0.3022 0.032 Uiso 1 1 calc R . . C17 C 0.6716(3) -0.0348(3) 0.1371(3) 0.0294(6) Uani 1 1 d . . . C18 C 0.5929(3) -0.1649(3) 0.0623(3) 0.0318(6) Uani 1 1 d . . . C19 C 0.4263(3) -0.3419(3) 0.0475(4) 0.0551(10) Uani 1 1 d . . . H19A H 0.4900 -0.4065 0.0552 0.066 Uiso 1 1 calc R . . H19B H 0.3936 -0.3528 -0.0388 0.066 Uiso 1 1 calc R . . C20 C 0.7158(3) 0.0504(3) 0.0800(3) 0.0386(7) Uani 1 1 d . . . H20A H 0.6911 0.0307 -0.0045 0.046 Uiso 1 1 calc R . . C21 C 0.7970(3) 0.1645(3) 0.1507(3) 0.0443(8) Uani 1 1 d . . . H21A H 0.8252 0.2242 0.1145 0.053 Uiso 1 1 calc R . . C22 C 0.8360(3) 0.1898(3) 0.2749(3) 0.0347(7) Uani 1 1 d . . . H22A H 0.8929 0.2661 0.3215 0.042 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 Cu1 0.01385(17) 0.02315(19) 0.02757(19) 0.00196(13) 0.00332(12) -0.00271(12) O1 0.0176(10) 0.0338(11) 0.0626(14) 0.0154(10) 0.0112(9) 0.0006(8) C1 0.0167(13) 0.0301(15) 0.0255(14) 0.0080(11) 0.0035(10) 0.0022(11) O1W 0.0577(15) 0.0487(14) 0.0576(16) 0.0109(12) 0.0314(12) 0.0055(12) O2 0.0173(9) 0.0283(11) 0.0395(11) 0.0082(9) 0.0084(8) 0.0028(7) N1 0.0200(11) 0.0213(12) 0.0316(13) 0.0053(9) 0.0051(9) 0.0008(9) C2 0.0180(13) 0.0247(14) 0.0275(14) 0.0082(11) 0.0054(11) 0.0018(10) O2W 0.0608(17) 0.0435(15) 0.095(2) -0.0067(14) -0.0138(15) 0.0072(13) O3 0.0137(9) 0.0316(11) 0.0418(12) 0.0138(9) 0.0042(8) 0.0014(8) N2 0.0522(17) 0.0364(15) 0.0372(15) 0.0169(12) -0.0139(12) -0.0223(12) C3 0.0213(13) 0.0172(13) 0.0267(14) 0.0030(10) 0.0056(11) 0.0028(10) O3W 0.128(3) 0.0596(19) 0.088(2) 0.0394(17) 0.056(2) 0.0278(18) O4 0.0537(14) 0.0276(12) 0.0537(15) 0.0141(11) -0.0148(11) -0.0088(10) N3 0.0210(11) 0.0261(12) 0.0307(13) 0.0049(10) 0.0041(9) -0.0021(9) C4 0.0168(12) 0.0217(13) 0.0257(14) 0.0068(11) 0.0042(10) 0.0005(10) O5 0.0455(13) 0.0492(14) 0.0391(13) -0.0060(11) 0.0126(10) -0.0080(11) N4 0.0327(13) 0.0274(13) 0.0383(14) -0.0042(11) 0.0079(11) -0.0072(10) C5 0.0217(14) 0.0236(14) 0.0189(13) 0.0041(10) 0.0037(10) -0.0022(11) O6 0.0275(11) 0.0200(11) 0.0557(14) 0.0078(9) 0.0028(9) -0.0021(8) C6 0.0190(13) 0.0246(15) 0.0488(18) 0.0088(13) 0.0100(12) 0.0051(11) C7 0.0295(15) 0.0174(14) 0.062(2) 0.0020(13) 0.0140(14) 0.0031(11) C8 0.0216(14) 0.0261(15) 0.0463(18) 0.0069(13) 0.0057(12) -0.0048(11) C9 0.0232(13) 0.0229(14) 0.0302(15) 0.0069(11) 0.0050(11) -0.0019(11) C10 0.0215(13) 0.0220(14) 0.0295(15) 0.0039(11) 0.0043(11) -0.0015(10) C11 0.0255(14) 0.0267(15) 0.0290(15) 0.0048(12) 0.0042(12) -0.0044(11) C12 0.056(2) 0.0384(18) 0.0252(16) 0.0044(13) -0.0052(14) -0.0205(15) C13 0.0291(15) 0.0322(16) 0.0290(15) 0.0095(12) 0.0016(12) 0.0007(12) C14 0.0375(17) 0.0279(15) 0.0393(18) 0.0153(13) 0.0082(13) -0.0005(12) C15 0.0237(14) 0.0234(14) 0.0383(17) 0.0051(12) 0.0055(12) -0.0016(11) C16 0.0194(13) 0.0293(15) 0.0309(15) 0.0089(12) 0.0041(11) -0.0044(11) C17 0.0226(14) 0.0269(15) 0.0356(16) 0.0075(12) 0.0027(12) 0.0020(11) C18 0.0233(14) 0.0317(16) 0.0330(16) 0.0031(13) 0.0007(12) 0.0006(12) C19 0.0383(18) 0.0256(17) 0.084(3) -0.0100(17) 0.0168(18) -0.0065(14) C20 0.0444(18) 0.0400(18) 0.0298(16) 0.0133(14) 0.0022(13) -0.0019(14) C21 0.052(2) 0.0360(18) 0.046(2) 0.0229(15) 0.0028(15) -0.0094(15) C22 0.0342(16) 0.0249(15) 0.0412(18) 0.0089(13) 0.0037(13) -0.0052(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 Cu1 O3 1.9691(17) 1_655 ? Cu1 N3 2.027(2) . ? Cu1 O2 2.0270(18) . ? Cu1 N1 2.035(2) . ? Cu1 O6 2.219(2) 2_656 ? O1 C1 1.243(3) . ? C1 O2 1.274(3) . ? C1 C2 1.506(3) . ? O1W H1WA 0.8477 . ? O1W H1WB 0.8514 . ? N1 C9 1.338(3) . ? N1 C15 1.341(4) . ? C2 C3 1.389(3) . ? C2 C8 1.395(4) . ? O2W H2WA 0.8520 . ? O2W H2WB 0.8480 . ? O3 C5 1.268(3) . ? O3 Cu1 1.9691(17) 1_455 ? N2 C11 1.321(4) . ? N2 C12 1.464(4) . ? N2 H3B 0.8600 . ? C3 C4 1.393(3) . ? C3 H3A 0.9300 . ? O3W H3WA 0.8457 . ? O3W H3WB 0.8517 . ? O4 C11 1.229(3) . ? N3 C16 1.338(3) . ? N3 C22 1.346(4) . ? C4 C6 1.390(4) . ? C4 C5 1.509(3) . ? O5 C18 1.241(3) . ? N4 C18 1.325(4) . ? N4 C19 1.450(4) . ? N4 H5A 0.8600 . ? C5 O6 1.235(3) . ? O6 Cu1 2.219(2) 2_656 ? C6 C7 1.384(4) . ? C6 H6A 0.9300 . ? C7 C8 1.383(4) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.382(4) . ? C9 H9A 0.9300 . ? C10 C13 1.394(4) . ? C10 C11 1.499(4) . ? C12 C19 1.492(5) 1_666 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.379(4) . ? C13 H13A 0.9300 . ? C14 C15 1.374(4) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.386(4) . ? C16 H16A 0.9300 . ? C17 C20 1.387(4) . ? C17 C18 1.500(4) . ? C19 C12 1.492(5) 1_444 ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.377(4) . ? C20 H20A 0.9300 . ? C21 C22 1.372(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? 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 O3 Cu1 N3 90.41(8) 1_655 . ? O3 Cu1 O2 147.83(8) 1_655 . ? N3 Cu1 O2 90.57(8) . . ? O3 Cu1 N1 87.39(8) 1_655 . ? N3 Cu1 N1 177.63(8) . . ? O2 Cu1 N1 91.77(8) . . ? O3 Cu1 O6 124.17(7) 1_655 2_656 ? N3 Cu1 O6 90.00(8) . 2_656 ? O2 Cu1 O6 87.98(7) . 2_656 ? N1 Cu1 O6 90.51(8) . 2_656 ? O1 C1 O2 122.3(2) . . ? O1 C1 C2 120.2(2) . . ? O2 C1 C2 117.5(2) . . ? H1WA O1W H1WB 107.8 . . ? C1 O2 Cu1 104.56(15) . . ? C9 N1 C15 117.8(2) . . ? C9 N1 Cu1 117.15(18) . . ? C15 N1 Cu1 125.08(18) . . ? C3 C2 C8 119.0(2) . . ? C3 C2 C1 120.9(2) . . ? C8 C2 C1 120.1(2) . . ? H2WA O2W H2WB 107.7 . . ? C5 O3 Cu1 125.45(17) . 1_455 ? C11 N2 C12 121.5(3) . . ? C11 N2 H3B 119.2 . . ? C12 N2 H3B 119.2 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? H3WA O3W H3WB 107.9 . . ? C16 N3 C22 118.3(2) . . ? C16 N3 Cu1 121.23(18) . . ? C22 N3 Cu1 120.38(18) . . ? C6 C4 C3 118.9(2) . . ? C6 C4 C5 121.3(2) . . ? C3 C4 C5 119.8(2) . . ? C18 N4 C19 121.1(3) . . ? C18 N4 H5A 119.5 . . ? C19 N4 H5A 119.5 . . ? O6 C5 O3 125.3(2) . . ? O6 C5 C4 118.3(2) . . ? O3 C5 C4 116.4(2) . . ? C5 O6 Cu1 161.98(18) . 2_656 ? C7 C6 C4 120.4(2) . . ? C7 C6 H6A 119.8 . . ? C4 C6 H6A 119.8 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C2 120.2(2) . . ? C7 C8 H8A 119.9 . . ? C2 C8 H8A 119.9 . . ? N1 C9 C10 123.6(2) . . ? N1 C9 H9A 118.2 . . ? C10 C9 H9A 118.2 . . ? C9 C10 C13 118.1(2) . . ? C9 C10 C11 117.0(2) . . ? C13 C10 C11 124.8(2) . . ? O4 C11 N2 121.5(3) . . ? O4 C11 C10 120.2(2) . . ? N2 C11 C10 118.2(3) . . ? N2 C12 C19 111.3(3) . 1_666 ? N2 C12 H12A 109.4 . . ? C19 C12 H12A 109.4 1_666 . ? N2 C12 H12B 109.4 . . ? C19 C12 H12B 109.4 1_666 . ? H12A C12 H12B 108.0 . . ? C14 C13 C10 118.2(3) . . ? C14 C13 H13A 120.9 . . ? C10 C13 H13A 120.9 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? N1 C15 C14 122.2(2) . . ? N1 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? N3 C16 C17 122.8(2) . . ? N3 C16 H16A 118.6 . . ? C17 C16 H16A 118.6 . . ? C16 C17 C20 118.3(2) . . ? C16 C17 C18 121.4(2) . . ? C20 C17 C18 120.1(3) . . ? O5 C18 N4 122.1(3) . . ? O5 C18 C17 120.7(3) . . ? N4 C18 C17 117.2(2) . . ? N4 C19 C12 112.6(3) . 1_444 ? N4 C19 H19A 109.1 . . ? C12 C19 H19A 109.1 1_444 . ? N4 C19 H19B 109.1 . . ? C12 C19 H19B 109.1 1_444 . ? H19A C19 H19B 107.8 . . ? C21 C20 C17 118.8(3) . . ? C21 C20 H20A 120.6 . . ? C17 C20 H20A 120.6 . . ? C22 C21 C20 119.8(3) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? N3 C22 C21 122.0(3) . . ? N3 C22 H22A 119.0 . . ? C21 C22 H22A 119.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 O2 Cu1 -2.9(3) . . . . ? C2 C1 O2 Cu1 176.69(18) . . . . ? O3 Cu1 O2 C1 -2.5(2) 1_655 . . . ? N3 Cu1 O2 C1 -94.19(17) . . . . ? N1 Cu1 O2 C1 85.39(17) . . . . ? O6 Cu1 O2 C1 175.83(17) 2_656 . . . ? O3 Cu1 N1 C9 44.71(19) 1_655 . . . ? N3 Cu1 N1 C9 67(2) . . . . ? O2 Cu1 N1 C9 -103.11(19) . . . . ? O6 Cu1 N1 C9 168.89(19) 2_656 . . . ? O3 Cu1 N1 C15 -134.2(2) 1_655 . . . ? N3 Cu1 N1 C15 -112(2) . . . . ? O2 Cu1 N1 C15 78.0(2) . . . . ? O6 Cu1 N1 C15 -10.0(2) 2_656 . . . ? O1 C1 C2 C3 167.6(3) . . . . ? O2 C1 C2 C3 -11.9(4) . . . . ? O1 C1 C2 C8 -10.4(4) . . . . ? O2 C1 C2 C8 170.0(2) . . . . ? C8 C2 C3 C4 2.5(4) . . . . ? C1 C2 C3 C4 -175.6(2) . . . . ? O3 Cu1 N3 C16 146.1(2) 1_655 . . . ? O2 Cu1 N3 C16 -66.1(2) . . . . ? N1 Cu1 N3 C16 124(2) . . . . ? O6 Cu1 N3 C16 21.9(2) 2_656 . . . ? O3 Cu1 N3 C22 -30.5(2) 1_655 . . . ? O2 Cu1 N3 C22 117.4(2) . . . . ? N1 Cu1 N3 C22 -52(2) . . . . ? O6 Cu1 N3 C22 -154.6(2) 2_656 . . . ? C2 C3 C4 C6 -2.0(4) . . . . ? C2 C3 C4 C5 179.0(2) . . . . ? Cu1 O3 C5 O6 22.2(4) 1_455 . . . ? Cu1 O3 C5 C4 -157.30(17) 1_455 . . . ? C6 C4 C5 O6 -163.1(3) . . . . ? C3 C4 C5 O6 15.8(4) . . . . ? C6 C4 C5 O3 16.4(4) . . . . ? C3 C4 C5 O3 -164.6(2) . . . . ? O3 C5 O6 Cu1 -12.2(8) . . . 2_656 ? C4 C5 O6 Cu1 167.3(5) . . . 2_656 ? C3 C4 C6 C7 -0.7(4) . . . . ? C5 C4 C6 C7 178.3(3) . . . . ? C4 C6 C7 C8 2.8(5) . . . . ? C6 C7 C8 C2 -2.3(5) . . . . ? C3 C2 C8 C7 -0.3(4) . . . . ? C1 C2 C8 C7 177.8(3) . . . . ? C15 N1 C9 C10 1.1(4) . . . . ? Cu1 N1 C9 C10 -177.9(2) . . . . ? N1 C9 C10 C13 -1.4(4) . . . . ? N1 C9 C10 C11 180.0(2) . . . . ? C12 N2 C11 O4 1.0(5) . . . . ? C12 N2 C11 C10 -178.6(3) . . . . ? C9 C10 C11 O4 23.0(4) . . . . ? C13 C10 C11 O4 -155.5(3) . . . . ? C9 C10 C11 N2 -157.4(3) . . . . ? C13 C10 C11 N2 24.1(4) . . . . ? C11 N2 C12 C19 -86.3(4) . . . 1_666 ? C9 C10 C13 C14 0.3(4) . . . . ? C11 C10 C13 C14 178.8(3) . . . . ? C10 C13 C14 C15 1.1(4) . . . . ? C9 N1 C15 C14 0.4(4) . . . . ? Cu1 N1 C15 C14 179.3(2) . . . . ? C13 C14 C15 N1 -1.5(4) . . . . ? C22 N3 C16 C17 3.0(4) . . . . ? Cu1 N3 C16 C17 -173.6(2) . . . . ? N3 C16 C17 C20 -2.6(4) . . . . ? N3 C16 C17 C18 172.3(2) . . . . ? C19 N4 C18 O5 3.5(5) . . . . ? C19 N4 C18 C17 -174.1(3) . . . . ? C16 C17 C18 O5 -139.4(3) . . . . ? C20 C17 C18 O5 35.4(4) . . . . ? C16 C17 C18 N4 38.2(4) . . . . ? C20 C17 C18 N4 -147.0(3) . . . . ? C18 N4 C19 C12 -169.6(3) . . . 1_444 ? C16 C17 C20 C21 0.0(4) . . . . ? C18 C17 C20 C21 -175.0(3) . . . . ? C17 C20 C21 C22 2.1(5) . . . . ? C16 N3 C22 C21 -0.7(4) . . . . ? Cu1 N3 C22 C21 175.9(2) . . . . ? C20 C21 C22 N3 -1.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.398 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.060 data_lj-2 _database_code_depnum_ccdc_archive 'CCDC 889600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 Cu N3 O6' _chemical_formula_weight 395.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9268(7) _cell_length_b 10.0557(11) _cell_length_c 11.1566(13) _cell_angle_alpha 104.553(2) _cell_angle_beta 99.146(2) _cell_angle_gamma 98.756(2) _cell_volume 727.43(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1136 _cell_measurement_theta_min 1.93 _cell_measurement_theta_max 25.98 _exptl_crystal_description BLOCK _exptl_crystal_colour Green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 1.544 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8015 _exptl_absorpt_correction_T_max 0.8245 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4182 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_unetI/netI 0.0612 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2824 _reflns_number_gt 2211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0498P)^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 2824 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.30954(7) 1.21753(4) 0.34085(4) 0.01999(15) Uani 1 1 d . . . O1 O 0.1758(4) 1.0305(2) 0.3338(2) 0.0269(6) Uani 1 1 d . . . O1W O 0.6441(4) 1.2007(3) 0.3764(3) 0.0367(8) Uani 1 1 d . . . H1WA H 0.739(7) 1.224(5) 0.351(4) 0.044 Uiso 1 1 d . . . H1WB H 0.606(7) 1.122(5) 0.356(4) 0.044 Uiso 1 1 d . . . N1 N -0.3584(4) 0.7221(3) 0.4634(3) 0.0209(7) Uani 1 1 d . . . H1A H -0.4312 0.6530 0.4779 0.025 Uiso 1 1 calc R . . H1B H -0.3892 0.8035 0.4803 0.025 Uiso 1 1 calc R . . C1 C 0.2547(5) 0.9266(3) 0.3438(3) 0.0212(8) Uani 1 1 d . . . O2 O 0.4352(4) 0.9227(2) 0.3483(3) 0.0324(7) Uani 1 1 d . . . N2 N 0.3249(4) 1.1679(3) 0.1556(3) 0.0208(7) Uani 1 1 d . . . C2 C 0.1140(5) 0.8007(3) 0.3526(3) 0.0187(8) Uani 1 1 d . . . O3 O -0.0297(4) 0.3058(2) 0.2739(3) 0.0342(7) Uani 1 1 d . . . N3 N 0.7636(4) 1.4056(3) 0.0252(3) 0.0287(8) Uani 1 1 d . . . H3B H 0.8011 1.3706 0.0858 0.034 Uiso 1 1 calc R . . C3 C -0.0637(5) 0.8159(3) 0.3933(3) 0.0188(8) Uani 1 1 d . . . H3A H -0.1010 0.9026 0.4086 0.023 Uiso 1 1 calc R . . O4 O 0.2890(3) 0.4153(2) 0.3469(2) 0.0210(6) Uani 1 1 d . . . C4 C -0.1859(5) 0.7017(3) 0.4111(3) 0.0168(7) Uani 1 1 d . . . O5 O 0.5162(4) 1.3880(3) -0.1406(2) 0.0331(7) Uani 1 1 d . . . C5 C -0.1340(5) 0.5713(3) 0.3832(3) 0.0189(8) Uani 1 1 d . . . H5A H -0.2174 0.4940 0.3917 0.023 Uiso 1 1 calc R . . C6 C 0.0438(5) 0.5563(3) 0.3424(3) 0.0181(8) Uani 1 1 d . . . C7 C 0.1023(6) 0.4148(3) 0.3180(3) 0.0202(8) Uani 1 1 d . . . C8 C 0.1671(5) 0.6705(3) 0.3276(3) 0.0186(8) Uani 1 1 d . . . H8A H 0.2857 0.6599 0.3008 0.022 Uiso 1 1 calc R . . C9 C 0.4351(5) 1.2636(4) 0.1163(3) 0.0215(8) Uani 1 1 d . . . H9A H 0.4998 1.3481 0.1752 0.026 Uiso 1 1 calc R . . C10 C 0.4569(5) 1.2424(4) -0.0074(3) 0.0208(8) Uani 1 1 d . . . C11 C 0.5820(5) 1.3522(4) -0.0484(4) 0.0230(8) Uani 1 1 d . . . C12 C 0.9005(5) 1.5204(4) 0.0073(4) 0.0276(9) Uani 1 1 d . . . H12A H 0.9210 1.6023 0.0794 0.033 Uiso 1 1 calc R . . H12B H 0.8429 1.5444 -0.0677 0.033 Uiso 1 1 calc R . . C13 C 0.3566(5) 1.1168(4) -0.0965(4) 0.0288(9) Uani 1 1 d . . . H13A H 0.3627 1.1013 -0.1814 0.035 Uiso 1 1 calc R . . C14 C 0.2482(6) 1.0164(4) -0.0557(4) 0.0301(9) Uani 1 1 d . . . H14A H 0.1834 0.9306 -0.1126 0.036 Uiso 1 1 calc R . . C15 C 0.2368(5) 1.0444(4) 0.0704(4) 0.0267(9) Uani 1 1 d . . . H15A H 0.1657 0.9752 0.0974 0.032 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 Cu1 0.0262(3) 0.0135(2) 0.0256(3) 0.00891(19) 0.01260(19) 0.00653(17) O1 0.0344(15) 0.0136(12) 0.0389(17) 0.0124(12) 0.0152(13) 0.0066(11) O1W 0.0261(17) 0.0424(18) 0.0399(19) 0.0094(16) 0.0091(14) 0.0033(14) N1 0.0220(16) 0.0160(15) 0.0292(18) 0.0086(14) 0.0140(14) 0.0049(12) C1 0.031(2) 0.0141(17) 0.019(2) 0.0032(15) 0.0123(16) 0.0017(15) O2 0.0266(15) 0.0217(14) 0.0551(19) 0.0158(14) 0.0184(14) 0.0051(11) N2 0.0205(16) 0.0181(15) 0.0254(18) 0.0057(14) 0.0092(13) 0.0048(12) C2 0.026(2) 0.0141(17) 0.0162(19) 0.0044(15) 0.0050(15) 0.0045(14) O3 0.0320(16) 0.0137(13) 0.0526(19) 0.0003(13) 0.0152(14) -0.0002(11) N3 0.0223(18) 0.0377(19) 0.0294(19) 0.0191(16) 0.0049(14) 0.0005(14) C3 0.0233(19) 0.0133(17) 0.022(2) 0.0070(15) 0.0052(16) 0.0060(14) O4 0.0232(14) 0.0162(12) 0.0274(14) 0.0080(11) 0.0091(11) 0.0077(10) C4 0.0193(18) 0.0179(17) 0.0146(18) 0.0052(15) 0.0035(15) 0.0064(14) O5 0.0333(16) 0.0420(17) 0.0265(16) 0.0167(14) 0.0062(13) 0.0038(13) C5 0.0220(19) 0.0153(17) 0.0183(19) 0.0040(15) 0.0047(15) 0.0011(14) C6 0.0235(19) 0.0127(16) 0.0181(19) 0.0029(15) 0.0045(15) 0.0056(14) C7 0.033(2) 0.0155(18) 0.0156(19) 0.0058(15) 0.0116(16) 0.0064(16) C8 0.0213(19) 0.0187(18) 0.0173(19) 0.0050(15) 0.0056(15) 0.0067(14) C9 0.0216(19) 0.0190(18) 0.023(2) 0.0042(16) 0.0057(16) 0.0032(15) C10 0.0174(18) 0.0246(19) 0.023(2) 0.0074(16) 0.0087(16) 0.0046(15) C11 0.023(2) 0.0244(19) 0.023(2) 0.0054(17) 0.0112(17) 0.0049(16) C12 0.025(2) 0.028(2) 0.032(2) 0.0154(18) 0.0064(18) 0.0000(16) C13 0.026(2) 0.035(2) 0.022(2) 0.0016(18) 0.0073(17) 0.0044(17) C14 0.026(2) 0.026(2) 0.031(2) 0.0001(18) 0.0046(18) -0.0031(17) C15 0.024(2) 0.021(2) 0.037(2) 0.0089(18) 0.0112(18) 0.0010(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 Cu1 O1 1.943(2) . ? Cu1 O4 2.000(2) 1_565 ? Cu1 N2 2.025(3) . ? Cu1 N1 2.071(3) 2_576 ? Cu1 O1W 2.328(3) . ? O1 C1 1.271(4) . ? O1W H1WA 0.78(5) . ? O1W H1WB 0.76(4) . ? N1 C4 1.430(4) . ? N1 Cu1 2.071(3) 2_576 ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? C1 O2 1.250(4) . ? C1 C2 1.510(5) . ? N2 C9 1.339(4) . ? N2 C15 1.345(4) . ? C2 C8 1.386(5) . ? C2 C3 1.394(5) . ? O3 C7 1.249(4) . ? N3 C11 1.338(5) . ? N3 C12 1.454(4) . ? N3 H3B 0.8600 . ? C3 C4 1.395(5) . ? C3 H3A 0.9300 . ? O4 C7 1.281(4) . ? O4 Cu1 2.000(2) 1_545 ? C4 C5 1.385(5) . ? O5 C11 1.218(4) . ? C5 C6 1.395(5) . ? C5 H5A 0.9300 . ? C6 C8 1.385(5) . ? C6 C7 1.509(5) . ? C8 H8A 0.9300 . ? C9 C10 1.379(5) . ? C9 H9A 0.9300 . ? C10 C13 1.396(5) . ? C10 C11 1.506(5) . ? C12 C12 1.518(7) 2_785 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.378(5) . ? C13 H13A 0.9300 . ? C14 C15 1.382(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O4 147.97(10) . 1_565 ? O1 Cu1 N2 94.76(11) . . ? O4 Cu1 N2 92.78(11) 1_565 . ? O1 Cu1 N1 91.07(11) . 2_576 ? O4 Cu1 N1 87.76(10) 1_565 2_576 ? N2 Cu1 N1 168.01(11) . 2_576 ? O1 Cu1 O1W 102.11(11) . . ? O4 Cu1 O1W 109.53(11) 1_565 . ? N2 Cu1 O1W 85.06(12) . . ? N1 Cu1 O1W 83.48(11) 2_576 . ? C1 O1 Cu1 127.8(2) . . ? Cu1 O1W H1WA 137(4) . . ? Cu1 O1W H1WB 86(4) . . ? H1WA O1W H1WB 114(5) . . ? C4 N1 Cu1 115.5(2) . 2_576 ? C4 N1 H1A 120.0 . . ? Cu1 N1 H1A 78.1 2_576 . ? C4 N1 H1B 120.0 . . ? Cu1 N1 H1B 77.0 2_576 . ? H1A N1 H1B 120.0 . . ? O2 C1 O1 125.4(3) . . ? O2 C1 C2 119.3(3) . . ? O1 C1 C2 115.3(3) . . ? C9 N2 C15 118.0(3) . . ? C9 N2 Cu1 117.5(2) . . ? C15 N2 Cu1 124.5(2) . . ? C8 C2 C3 119.6(3) . . ? C8 C2 C1 119.8(3) . . ? C3 C2 C1 120.4(3) . . ? C11 N3 C12 122.8(3) . . ? C11 N3 H3B 118.6 . . ? C12 N3 H3B 118.6 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C7 O4 Cu1 106.1(2) . 1_545 ? C5 C4 C3 119.6(3) . . ? C5 C4 N1 120.8(3) . . ? C3 C4 N1 119.5(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C8 C6 C5 120.4(3) . . ? C8 C6 C7 120.5(3) . . ? C5 C6 C7 119.1(3) . . ? O3 C7 O4 123.9(3) . . ? O3 C7 C6 119.7(3) . . ? O4 C7 C6 116.4(3) . . ? C6 C8 C2 120.1(3) . . ? C6 C8 H8A 119.9 . . ? C2 C8 H8A 119.9 . . ? N2 C9 C10 123.0(3) . . ? N2 C9 H9A 118.5 . . ? C10 C9 H9A 118.5 . . ? C9 C10 C13 118.6(3) . . ? C9 C10 C11 121.6(3) . . ? C13 C10 C11 119.7(3) . . ? O5 C11 N3 124.7(3) . . ? O5 C11 C10 120.8(3) . . ? N3 C11 C10 114.6(3) . . ? N3 C12 C12 110.6(4) . 2_785 ? N3 C12 H12A 109.5 . . ? C12 C12 H12A 109.5 2_785 . ? N3 C12 H12B 109.5 . . ? C12 C12 H12B 109.5 2_785 . ? H12A C12 H12B 108.1 . . ? C14 C13 C10 118.5(3) . . ? C14 C13 H13A 120.8 . . ? C10 C13 H13A 120.8 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? N2 C15 C14 122.4(3) . . ? N2 C15 H15A 118.8 . . ? C14 C15 H15A 118.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 O1 C1 -172.3(2) 1_565 . . . ? N2 Cu1 O1 C1 84.7(3) . . . . ? N1 Cu1 O1 C1 -84.8(3) 2_576 . . . ? O1W Cu1 O1 C1 -1.3(3) . . . . ? Cu1 O1 C1 O2 -7.2(5) . . . . ? Cu1 O1 C1 C2 171.8(2) . . . . ? O1 Cu1 N2 C9 -170.8(3) . . . . ? O4 Cu1 N2 C9 40.4(3) 1_565 . . . ? N1 Cu1 N2 C9 -51.9(7) 2_576 . . . ? O1W Cu1 N2 C9 -69.0(3) . . . . ? O1 Cu1 N2 C15 7.3(3) . . . . ? O4 Cu1 N2 C15 -141.6(3) 1_565 . . . ? N1 Cu1 N2 C15 126.1(5) 2_576 . . . ? O1W Cu1 N2 C15 109.0(3) . . . . ? O2 C1 C2 C8 -19.4(5) . . . . ? O1 C1 C2 C8 161.6(3) . . . . ? O2 C1 C2 C3 156.7(3) . . . . ? O1 C1 C2 C3 -22.3(5) . . . . ? C8 C2 C3 C4 1.2(5) . . . . ? C1 C2 C3 C4 -174.9(3) . . . . ? C2 C3 C4 C5 -2.6(5) . . . . ? C2 C3 C4 N1 174.5(3) . . . . ? Cu1 N1 C4 C5 90.7(3) 2_576 . . . ? Cu1 N1 C4 C3 -86.4(3) 2_576 . . . ? C3 C4 C5 C6 2.5(5) . . . . ? N1 C4 C5 C6 -174.6(3) . . . . ? C4 C5 C6 C8 -1.1(5) . . . . ? C4 C5 C6 C7 177.4(3) . . . . ? Cu1 O4 C7 O3 -11.3(4) 1_545 . . . ? Cu1 O4 C7 C6 167.4(2) 1_545 . . . ? C8 C6 C7 O3 -146.7(4) . . . . ? C5 C6 C7 O3 34.9(5) . . . . ? C8 C6 C7 O4 34.6(5) . . . . ? C5 C6 C7 O4 -143.9(3) . . . . ? C5 C6 C8 C2 -0.3(5) . . . . ? C7 C6 C8 C2 -178.8(3) . . . . ? C3 C2 C8 C6 0.3(5) . . . . ? C1 C2 C8 C6 176.4(3) . . . . ? C15 N2 C9 C10 2.0(5) . . . . ? Cu1 N2 C9 C10 -179.9(3) . . . . ? N2 C9 C10 C13 1.3(5) . . . . ? N2 C9 C10 C11 180.0(3) . . . . ? C12 N3 C11 O5 3.9(6) . . . . ? C12 N3 C11 C10 -175.0(3) . . . . ? C9 C10 C11 O5 -130.4(4) . . . . ? C13 C10 C11 O5 48.2(5) . . . . ? C9 C10 C11 N3 48.6(5) . . . . ? C13 C10 C11 N3 -132.8(4) . . . . ? C11 N3 C12 C12 -125.1(4) . . . 2_785 ? C9 C10 C13 C14 -3.3(5) . . . . ? C11 C10 C13 C14 178.0(3) . . . . ? C10 C13 C14 C15 2.1(6) . . . . ? C9 N2 C15 C14 -3.3(5) . . . . ? Cu1 N2 C15 C14 178.7(3) . . . . ? C13 C14 C15 N2 1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.533 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.091 data_lj-5 _database_code_depnum_ccdc_archive 'CCDC 891322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 Cu3 N4 O12' _chemical_formula_weight 849.19 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 8.0878(7) _cell_length_b 8.8044(8) _cell_length_c 11.3643(10) _cell_angle_alpha 85.133(2) _cell_angle_beta 75.9090(10) _cell_angle_gamma 87.445(2) _cell_volume 781.81(12) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2886 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.15 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.804 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 429 _exptl_absorpt_coefficient_mu 2.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_T_max 0.730 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4135 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_unetI/netI 0.0194 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2747 _reflns_number_gt 2510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0492P)^2^+0.6423P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2747 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.10123(4) 0.62797(3) 0.41819(3) 0.02101(12) Uani 1 1 d . . . O1 O 0.2779(3) 1.1570(2) 0.61598(19) 0.0350(5) Uani 1 1 d . . . N1 N 0.0906(3) 0.7747(3) 0.41524(19) 0.0232(5) Uani 1 1 d . . . C1 C 0.1973(4) 0.8221(4) 0.3101(3) 0.0342(7) Uani 1 1 d . . . H1A H 0.1904 0.7784 0.2397 0.041 Uiso 1 1 calc R . . Cu2 Cu -0.5000 0.5000 0.5000 0.02727(14) Uani 1 2 d S . . O2 O -0.1740(2) 0.6362(2) 0.59794(16) 0.0287(4) Uani 1 1 d . . . N2 N 0.1800(3) 0.9457(3) 0.7328(2) 0.0375(6) Uani 1 1 d . . . H2B H 0.1569 0.8509 0.7351 0.045 Uiso 1 1 calc R . . C2 C 0.3165(4) 0.9318(4) 0.3006(3) 0.0420(8) Uani 1 1 d . . . H2A H 0.3869 0.9620 0.2253 0.050 Uiso 1 1 calc R . . O3 O -0.4501(3) 0.5787(3) 0.64295(19) 0.0536(7) Uani 1 1 d . . . C3 C 0.3308(4) 0.9969(3) 0.4042(3) 0.0315(6) Uani 1 1 d . . . H3A H 0.4090 1.0727 0.3998 0.038 Uiso 1 1 calc R . . O4 O -0.0230(2) 0.4204(2) 0.74790(16) 0.0294(4) Uani 1 1 d . . . C4 C 0.2250(3) 0.9458(3) 0.5149(2) 0.0239(5) Uani 1 1 d . . . O5 O 0.0989(2) 0.6265(2) 0.78899(18) 0.0333(5) Uani 1 1 d . . . C5 C 0.1079(3) 0.8351(3) 0.5165(2) 0.0231(5) Uani 1 1 d . . . H5A H 0.0381 0.8009 0.5909 0.028 Uiso 1 1 calc R . . O6 O -0.2685(2) 0.4837(2) 0.42346(17) 0.0294(4) Uani 1 1 d . . . C6 C 0.2306(3) 1.0245(3) 0.6265(3) 0.0266(6) Uani 1 1 d . . . C7 C 0.1632(5) 1.0182(4) 0.8463(3) 0.0489(9) Uani 1 1 d . . . H7A H 0.1520 1.1278 0.8310 0.059 Uiso 1 1 calc R . . H7B H 0.2656 0.9970 0.8756 0.059 Uiso 1 1 calc R . . C8 C 0.0127(5) 0.9626(4) 0.9413(3) 0.0465(8) Uani 1 1 d . . . H8A H 0.0260 0.8533 0.9575 0.056 Uiso 1 1 calc R . . H8B H -0.0886 0.9808 0.9103 0.056 Uiso 1 1 calc R . . C10 C -0.3168(3) 0.6125(3) 0.6701(2) 0.0275(6) Uani 1 1 d . . . C11 C -0.3342(3) 0.6342(3) 0.8027(2) 0.0252(6) Uani 1 1 d . . . C12 C -0.4927(4) 0.6840(4) 0.8706(3) 0.0358(7) Uani 1 1 d . . . H12A H -0.5831 0.7019 0.8335 0.043 Uiso 1 1 calc R . . C13 C -0.5156(4) 0.7067(4) 0.9921(3) 0.0426(8) Uani 1 1 d . . . H13A H -0.6209 0.7416 1.0361 0.051 Uiso 1 1 calc R . . C14 C -0.3838(4) 0.6779(4) 1.0487(3) 0.0402(7) Uani 1 1 d . . . H14A H -0.4005 0.6918 1.1311 0.048 Uiso 1 1 calc R . . C15 C -0.2263(4) 0.6283(3) 0.9827(2) 0.0315(6) Uani 1 1 d . . . H15A H -0.1374 0.6095 1.0211 0.038 Uiso 1 1 calc R . . C16 C -0.1994(3) 0.6062(3) 0.8595(2) 0.0241(5) Uani 1 1 d . . . C17 C -0.0266(3) 0.5492(3) 0.7928(2) 0.0236(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01923(18) 0.02815(19) 0.01627(18) -0.00540(12) -0.00351(12) -0.00438(13) O1 0.0385(12) 0.0277(11) 0.0442(12) -0.0077(9) -0.0178(10) -0.0041(9) N1 0.0212(11) 0.0287(11) 0.0201(11) -0.0040(9) -0.0047(9) -0.0029(9) C1 0.0360(16) 0.0431(17) 0.0225(14) -0.0094(12) -0.0002(12) -0.0140(13) Cu2 0.0192(2) 0.0410(3) 0.0226(2) -0.0075(2) -0.00438(18) -0.00482(19) O2 0.0255(10) 0.0445(11) 0.0156(9) -0.0028(8) -0.0018(7) -0.0121(8) N2 0.0497(16) 0.0367(14) 0.0278(13) -0.0113(11) -0.0074(11) -0.0141(12) C2 0.0381(17) 0.055(2) 0.0278(15) -0.0076(14) 0.0056(13) -0.0190(15) O3 0.0234(11) 0.113(2) 0.0282(11) -0.0295(13) -0.0024(9) -0.0143(12) C3 0.0235(14) 0.0346(15) 0.0361(16) -0.0051(12) -0.0042(12) -0.0090(11) O4 0.0339(11) 0.0288(10) 0.0231(9) -0.0079(8) 0.0005(8) -0.0064(8) C4 0.0196(12) 0.0259(13) 0.0277(14) -0.0051(11) -0.0080(10) 0.0018(10) O5 0.0270(10) 0.0401(11) 0.0344(11) -0.0159(9) -0.0055(8) -0.0052(9) C5 0.0206(12) 0.0272(13) 0.0224(13) -0.0043(10) -0.0062(10) 0.0010(10) O6 0.0186(9) 0.0399(11) 0.0296(10) -0.0135(8) -0.0007(7) -0.0073(8) C6 0.0213(13) 0.0290(14) 0.0317(15) -0.0086(11) -0.0092(11) 0.0013(11) C7 0.059(2) 0.059(2) 0.0301(16) -0.0191(15) -0.0038(15) -0.0223(17) C8 0.056(2) 0.055(2) 0.0295(17) -0.0137(15) -0.0067(15) -0.0144(17) C10 0.0243(14) 0.0357(15) 0.0231(14) -0.0051(11) -0.0052(11) -0.0054(11) C11 0.0247(13) 0.0311(14) 0.0188(12) -0.0057(10) -0.0011(10) -0.0072(11) C12 0.0251(14) 0.0492(18) 0.0318(16) -0.0096(13) -0.0020(12) -0.0029(13) C13 0.0337(17) 0.056(2) 0.0320(16) -0.0187(15) 0.0091(13) -0.0038(15) C14 0.0466(19) 0.0524(19) 0.0186(14) -0.0135(13) 0.0025(13) -0.0070(15) C15 0.0361(16) 0.0392(16) 0.0195(13) -0.0062(11) -0.0049(11) -0.0077(13) C16 0.0267(14) 0.0260(13) 0.0190(12) -0.0042(10) -0.0019(10) -0.0073(11) C17 0.0285(14) 0.0278(14) 0.0155(12) -0.0024(10) -0.0064(10) -0.0029(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 Cu1 O6 1.8834(18) . ? Cu1 O4 1.9820(18) 2_566 ? Cu1 O2 1.9901(18) . ? Cu1 N1 2.055(2) . ? Cu1 O1 2.384(2) 2_576 ? O1 C6 1.230(3) . ? O1 Cu1 2.383(2) 2_576 ? N1 C1 1.339(4) . ? N1 C5 1.348(3) . ? C1 C2 1.375(4) . ? Cu2 O6 1.8677(18) 2_466 ? Cu2 O6 1.8677(18) . ? Cu2 O3 1.954(2) . ? Cu2 O3 1.954(2) 2_466 ? O2 C10 1.258(3) . ? N2 C6 1.323(4) . ? N2 C7 1.462(4) . ? C2 C3 1.383(4) . ? O3 C10 1.246(3) . ? C3 C4 1.390(4) . ? O4 C17 1.279(3) . ? O4 Cu1 1.9820(18) 2_566 ? C4 C5 1.385(4) . ? C4 C6 1.507(4) . ? O5 C17 1.237(3) . ? C7 C8 1.487(5) . ? C8 C8 1.503(6) 2_577 ? C10 C11 1.507(4) . ? C11 C12 1.399(4) . ? C11 C16 1.400(4) . ? C12 C13 1.378(4) . ? C13 C14 1.378(5) . ? C14 C15 1.384(4) . ? C15 C16 1.393(4) . ? C16 C17 1.505(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Cu1 O4 91.91(8) . 2_566 ? O6 Cu1 O2 90.71(8) . . ? O4 Cu1 O2 163.33(8) 2_566 . ? O6 Cu1 N1 176.51(9) . . ? O4 Cu1 N1 87.56(8) 2_566 . ? O2 Cu1 N1 88.82(8) . . ? O6 Cu1 O1 94.75(8) . 2_576 ? O4 Cu1 O1 103.78(8) 2_566 2_576 ? O2 Cu1 O1 92.40(8) . 2_576 ? N1 Cu1 O1 88.72(8) . 2_576 ? C6 O1 Cu1 123.38(18) . 2_576 ? C1 N1 C5 117.1(2) . . ? C1 N1 Cu1 120.70(18) . . ? C5 N1 Cu1 122.03(18) . . ? N1 C1 C2 123.4(3) . . ? O6 Cu2 O6 179.999(2) 2_466 . ? O6 Cu2 O3 88.16(8) 2_466 . ? O6 Cu2 O3 91.84(8) . . ? O6 Cu2 O3 91.84(8) 2_466 2_466 ? O6 Cu2 O3 88.16(8) . 2_466 ? O3 Cu2 O3 180.0 . 2_466 ? C10 O2 Cu1 130.28(17) . . ? C6 N2 C7 120.6(3) . . ? C1 C2 C3 119.4(3) . . ? C10 O3 Cu2 134.19(19) . . ? C2 C3 C4 118.2(3) . . ? C17 O4 Cu1 125.89(17) . 2_566 ? C5 C4 C3 118.9(2) . . ? C5 C4 C6 122.5(2) . . ? C3 C4 C6 118.3(2) . . ? N1 C5 C4 123.0(2) . . ? Cu2 O6 Cu1 126.51(10) . . ? O1 C6 N2 123.2(3) . . ? O1 C6 C4 119.9(3) . . ? N2 C6 C4 116.9(2) . . ? N2 C7 C8 111.6(3) . . ? C7 C8 C8 113.5(4) . 2_577 ? O3 C10 O2 126.7(2) . . ? O3 C10 C11 115.4(2) . . ? O2 C10 C11 117.8(2) . . ? C12 C11 C16 119.4(2) . . ? C12 C11 C10 117.9(2) . . ? C16 C11 C10 122.7(2) . . ? C13 C12 C11 120.4(3) . . ? C14 C13 C12 120.5(3) . . ? C13 C14 C15 119.8(3) . . ? C14 C15 C16 120.8(3) . . ? C15 C16 C11 119.1(2) . . ? C15 C16 C17 118.6(2) . . ? C11 C16 C17 122.3(2) . . ? O5 C17 O4 125.7(2) . . ? O5 C17 C16 118.4(2) . . ? O4 C17 C16 115.9(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.593 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.074 data_lj-6 _database_code_depnum_ccdc_archive 'CCDC 891323' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Cu N2 O6' _chemical_formula_weight 407.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9159(12) _cell_length_b 11.620(2) _cell_length_c 12.661(3) _cell_angle_alpha 74.184(4) _cell_angle_beta 80.552(4) _cell_angle_gamma 81.929(4) _cell_volume 821.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1138 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.15 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 418 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3721 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0688 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2836 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0484P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2836 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.42449(8) 0.10794(4) 0.53012(4) 0.02595(17) Uani 1 1 d . . . O1 O 0.6622(4) 0.1621(2) 0.4065(2) 0.0278(6) Uani 1 1 d . . . N1 N 0.2056(5) 0.2518(3) 0.4788(2) 0.0243(7) Uani 1 1 d . . . C1 C 0.8070(6) 0.0984(3) 0.3550(3) 0.0224(9) Uani 1 1 d . . . O1W O 0.6114(6) 0.6982(3) 0.2992(3) 0.0559(10) Uani 1 1 d . . . H1WA H 0.5770 0.6614 0.2516 0.067 Uiso 1 1 d G . . H1WB H 0.5426 0.7671 0.2834 0.067 Uiso 1 1 d G . . O2 O 0.8166(4) -0.0142(2) 0.3697(2) 0.0265(6) Uani 1 1 d . . . C2 C 0.9715(6) 0.1670(3) 0.2633(3) 0.0229(9) Uani 1 1 d . . . O3 O 1.4020(6) -0.0720(3) 0.2482(3) 0.0527(9) Uani 1 1 d . . . N3 N 0.0890(6) 0.6364(3) 0.2156(3) 0.0359(9) Uani 1 1 d . . . C3 C 0.8891(7) 0.2809(4) 0.2036(3) 0.0318(10) Uani 1 1 d . . . H3A H 0.7392 0.3119 0.2234 0.038 Uiso 1 1 calc R . . O4 O 1.3359(4) 0.0014(2) 0.3967(2) 0.0284(6) Uani 1 1 d . . . C4 C 1.0243(8) 0.3479(4) 0.1167(4) 0.0417(11) Uani 1 1 d . . . H4A H 0.9658 0.4235 0.0783 0.050 Uiso 1 1 calc R . . C5 C 1.2478(8) 0.3033(4) 0.0861(4) 0.0467(13) Uani 1 1 d . . . H5A H 1.3408 0.3488 0.0276 0.056 Uiso 1 1 calc R . . C6 C 1.3312(7) 0.1903(4) 0.1435(3) 0.0375(11) Uani 1 1 d . . . H6A H 1.4801 0.1596 0.1217 0.045 Uiso 1 1 calc R . . C7 C 1.1979(6) 0.1212(3) 0.2331(3) 0.0244(9) Uani 1 1 d . . . C8 C 1.3172(6) 0.0055(4) 0.2960(3) 0.0275(9) Uani 1 1 d . . . O9 O 0.4352(5) 0.5257(3) 0.2190(3) 0.0529(9) Uani 1 1 d . . . C16 C -0.0115(7) 0.2615(3) 0.5282(3) 0.0290(9) Uani 1 1 d . . . H16A H -0.0592 0.2001 0.5889 0.035 Uiso 1 1 calc R . . C17 C -0.1667(7) 0.3585(4) 0.4926(3) 0.0330(10) Uani 1 1 d . . . H17A H -0.3167 0.3621 0.5288 0.040 Uiso 1 1 calc R . . C18 C -0.0994(7) 0.4503(4) 0.4032(3) 0.0356(10) Uani 1 1 d . . . H18A H -0.2035 0.5159 0.3776 0.043 Uiso 1 1 calc R . . C19 C 0.1271(7) 0.4435(3) 0.3518(3) 0.0270(9) Uani 1 1 d . . . C20 C 0.2707(7) 0.3430(3) 0.3917(3) 0.0279(9) Uani 1 1 d . . . H20A H 0.4215 0.3374 0.3569 0.033 Uiso 1 1 calc R . . C21 C 0.2285(8) 0.5390(4) 0.2549(3) 0.0351(10) Uani 1 1 d . . . C22 C 0.1727(8) 0.7331(4) 0.1207(3) 0.0398(11) Uani 1 1 d . . . H22A H 0.1992 0.7049 0.0539 0.048 Uiso 1 1 calc R . . H22B H 0.3180 0.7538 0.1327 0.048 Uiso 1 1 calc R . . C27 C 0.0007(8) 0.8432(4) 0.1059(3) 0.0372(11) Uani 1 1 d . . . H27A H -0.0260 0.8711 0.1729 0.045 Uiso 1 1 calc R . . H27B H -0.1445 0.8223 0.0940 0.045 Uiso 1 1 calc R . . C28 C 0.0844(7) 0.9439(3) 0.0085(3) 0.0381(11) Uani 1 1 d . . . H28A H 0.2301 0.9640 0.0206 0.046 Uiso 1 1 calc R . . H28B H 0.1112 0.9156 -0.0582 0.046 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 Cu1 0.0192(3) 0.0222(3) 0.0292(3) 0.0040(2) -0.0025(2) 0.00007(18) O1 0.0247(15) 0.0205(14) 0.0314(15) 0.0010(12) 0.0006(13) -0.0001(11) N1 0.0239(19) 0.0205(17) 0.0251(18) -0.0011(14) -0.0003(15) -0.0038(14) C1 0.014(2) 0.027(2) 0.021(2) 0.0058(17) -0.0078(16) -0.0009(16) O1W 0.044(2) 0.044(2) 0.065(3) 0.0065(18) -0.0096(19) 0.0055(17) O2 0.0178(14) 0.0233(15) 0.0315(15) 0.0028(12) -0.0026(12) 0.0007(11) C2 0.021(2) 0.025(2) 0.022(2) 0.0011(16) -0.0079(17) -0.0036(16) O3 0.062(2) 0.043(2) 0.054(2) -0.0216(17) -0.0170(18) 0.0217(17) N3 0.044(2) 0.0199(18) 0.033(2) 0.0090(15) -0.0050(17) 0.0025(15) C3 0.023(2) 0.029(2) 0.036(2) 0.0015(19) -0.0024(19) 0.0014(17) O4 0.0202(15) 0.0331(16) 0.0258(16) 0.0007(12) -0.0037(12) 0.0016(12) C4 0.048(3) 0.030(2) 0.036(3) 0.010(2) -0.005(2) -0.003(2) C5 0.041(3) 0.046(3) 0.037(3) 0.014(2) 0.005(2) -0.011(2) C6 0.022(2) 0.042(3) 0.039(3) 0.001(2) 0.005(2) -0.0023(19) C7 0.021(2) 0.029(2) 0.020(2) -0.0015(17) -0.0039(17) -0.0019(16) C8 0.017(2) 0.027(2) 0.035(3) -0.0024(19) -0.0051(19) -0.0014(16) O9 0.038(2) 0.0342(18) 0.063(2) 0.0146(16) 0.0091(17) 0.0044(14) C16 0.029(2) 0.025(2) 0.031(2) -0.0031(18) -0.0037(19) -0.0029(17) C17 0.025(2) 0.029(2) 0.041(3) -0.005(2) -0.001(2) 0.0008(17) C18 0.032(3) 0.026(2) 0.042(3) 0.002(2) -0.011(2) 0.0049(18) C19 0.027(2) 0.024(2) 0.026(2) 0.0007(17) -0.0042(18) 0.0017(17) C20 0.028(2) 0.023(2) 0.029(2) -0.0027(18) -0.0012(19) -0.0017(17) C21 0.038(3) 0.023(2) 0.038(3) 0.0000(19) -0.004(2) 0.0014(18) C22 0.041(3) 0.030(2) 0.036(3) 0.009(2) -0.004(2) 0.001(2) C27 0.044(3) 0.028(2) 0.032(2) 0.0040(19) -0.006(2) 0.0014(19) C28 0.042(3) 0.031(2) 0.031(2) 0.004(2) -0.003(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.941(3) 2_756 ? Cu1 O1 1.952(3) . ? Cu1 O2 1.979(2) 2_656 ? Cu1 N1 1.993(3) . ? Cu1 Cu1 2.8042(11) 2_656 ? O1 C1 1.268(4) . ? N1 C16 1.337(5) . ? N1 C20 1.351(4) . ? C1 O2 1.265(4) . ? C1 C2 1.508(5) . ? O1W H1WA 0.89(4) . ? O1W H1WB 0.8329 . ? O2 Cu1 1.979(2) 2_656 ? C2 C3 1.398(5) . ? C2 C7 1.402(5) . ? O3 C8 1.225(5) . ? N3 C21 1.332(5) . ? N3 C22 1.475(5) . ? C3 C4 1.369(5) . ? C3 H3A 0.9300 . ? O4 C8 1.285(4) . ? O4 Cu1 1.941(3) 2_756 ? C4 C5 1.385(6) . ? C4 H4A 0.9300 . ? C5 C6 1.383(6) . ? C5 H5A 0.9300 . ? C6 C7 1.394(5) . ? C6 H6A 0.9300 . ? C7 C8 1.508(5) . ? O9 C21 1.237(5) . ? C16 C17 1.373(5) . ? C16 H16A 0.9300 . ? C17 C18 1.375(5) . ? C17 H17A 0.9300 . ? C18 C19 1.392(5) . ? C18 H18A 0.9300 . ? C19 C20 1.371(5) . ? C19 C21 1.517(5) . ? C20 H20A 0.9300 . ? C22 C27 1.508(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C27 C28 1.519(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C28 1.516(8) 2_575 ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? 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 O4 Cu1 O1 87.44(11) 2_756 . ? O4 Cu1 O2 90.91(10) 2_756 2_656 ? O1 Cu1 O2 161.98(11) . 2_656 ? O4 Cu1 N1 163.07(12) 2_756 . ? O1 Cu1 N1 92.64(11) . . ? O2 Cu1 N1 94.09(11) 2_656 . ? O4 Cu1 Cu1 60.51(8) 2_756 2_656 ? O1 Cu1 Cu1 79.58(8) . 2_656 ? O2 Cu1 Cu1 84.00(8) 2_656 2_656 ? N1 Cu1 Cu1 136.11(9) . 2_656 ? C1 O1 Cu1 128.0(2) . . ? C16 N1 C20 117.4(3) . . ? C16 N1 Cu1 121.5(2) . . ? C20 N1 Cu1 121.1(3) . . ? O2 C1 O1 126.2(3) . . ? O2 C1 C2 118.3(3) . . ? O1 C1 C2 115.4(3) . . ? H1WA O1W H1WB 105.5 . . ? C1 O2 Cu1 121.1(2) . 2_656 ? C3 C2 C7 118.9(3) . . ? C3 C2 C1 117.5(3) . . ? C7 C2 C1 123.6(3) . . ? C21 N3 C22 120.9(4) . . ? C4 C3 C2 121.5(4) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C8 O4 Cu1 119.5(2) . 2_756 ? C3 C4 C5 120.1(4) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 119.2(4) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C5 C6 C7 121.7(4) . . ? C5 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? C6 C7 C2 118.6(4) . . ? C6 C7 C8 116.4(3) . . ? C2 C7 C8 124.8(3) . . ? O3 C8 O4 125.0(4) . . ? O3 C8 C7 119.9(4) . . ? O4 C8 C7 114.9(3) . . ? N1 C16 C17 122.5(4) . . ? N1 C16 H16A 118.8 . . ? C17 C16 H16A 118.8 . . ? C16 C17 C18 119.7(4) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C17 C18 C19 118.9(4) . . ? C17 C18 H18A 120.5 . . ? C19 C18 H18A 120.5 . . ? C20 C19 C18 117.8(3) . . ? C20 C19 C21 117.2(3) . . ? C18 C19 C21 125.0(4) . . ? N1 C20 C19 123.7(4) . . ? N1 C20 H20A 118.1 . . ? C19 C20 H20A 118.1 . . ? O9 C21 N3 123.3(4) . . ? O9 C21 C19 119.4(4) . . ? N3 C21 C19 117.3(4) . . ? N3 C22 C27 111.0(3) . . ? N3 C22 H22A 109.4 . . ? C27 C22 H22A 109.4 . . ? N3 C22 H22B 109.4 . . ? C27 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C27 C28 111.7(3) . . ? C22 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? C22 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C28 C28 C27 113.0(4) 2_575 . ? C28 C28 H28A 109.0 2_575 . ? C27 C28 H28A 109.0 . . ? C28 C28 H28B 109.0 2_575 . ? C27 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 O1 C1 51.7(3) 2_756 . . . ? O2 Cu1 O1 C1 -33.3(5) 2_656 . . . ? N1 Cu1 O1 C1 -145.2(3) . . . . ? Cu1 Cu1 O1 C1 -8.7(3) 2_656 . . . ? O4 Cu1 N1 C16 -96.6(5) 2_756 . . . ? O1 Cu1 N1 C16 173.5(3) . . . . ? O2 Cu1 N1 C16 10.2(3) 2_656 . . . ? Cu1 Cu1 N1 C16 95.8(3) 2_656 . . . ? O4 Cu1 N1 C20 84.1(5) 2_756 . . . ? O1 Cu1 N1 C20 -5.8(3) . . . . ? O2 Cu1 N1 C20 -169.0(3) 2_656 . . . ? Cu1 Cu1 N1 C20 -83.4(3) 2_656 . . . ? Cu1 O1 C1 O2 4.6(5) . . . . ? Cu1 O1 C1 C2 -179.4(2) . . . . ? O1 C1 O2 Cu1 6.5(5) . . . 2_656 ? C2 C1 O2 Cu1 -169.5(2) . . . 2_656 ? O2 C1 C2 C3 142.7(4) . . . . ? O1 C1 C2 C3 -33.7(5) . . . . ? O2 C1 C2 C7 -35.2(5) . . . . ? O1 C1 C2 C7 148.4(4) . . . . ? C7 C2 C3 C4 0.1(6) . . . . ? C1 C2 C3 C4 -177.9(4) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C4 C5 C6 C7 -1.6(7) . . . . ? C5 C6 C7 C2 1.7(6) . . . . ? C5 C6 C7 C8 -173.7(4) . . . . ? C3 C2 C7 C6 -1.0(6) . . . . ? C1 C2 C7 C6 176.9(4) . . . . ? C3 C2 C7 C8 174.0(4) . . . . ? C1 C2 C7 C8 -8.2(6) . . . . ? Cu1 O4 C8 O3 17.7(5) 2_756 . . . ? Cu1 O4 C8 C7 -156.9(2) 2_756 . . . ? C6 C7 C8 O3 -59.8(5) . . . . ? C2 C7 C8 O3 125.2(4) . . . . ? C6 C7 C8 O4 115.1(4) . . . . ? C2 C7 C8 O4 -59.9(5) . . . . ? C20 N1 C16 C17 0.9(6) . . . . ? Cu1 N1 C16 C17 -178.4(3) . . . . ? N1 C16 C17 C18 -0.2(6) . . . . ? C16 C17 C18 C19 -1.0(6) . . . . ? C17 C18 C19 C20 1.6(6) . . . . ? C17 C18 C19 C21 -178.1(4) . . . . ? C16 N1 C20 C19 -0.2(6) . . . . ? Cu1 N1 C20 C19 179.1(3) . . . . ? C18 C19 C20 N1 -1.1(6) . . . . ? C21 C19 C20 N1 178.7(4) . . . . ? C22 N3 C21 O9 3.4(7) . . . . ? C22 N3 C21 C19 -179.3(4) . . . . ? C20 C19 C21 O9 -3.0(6) . . . . ? C18 C19 C21 O9 176.8(4) . . . . ? C20 C19 C21 N3 179.7(4) . . . . ? C18 C19 C21 N3 -0.6(6) . . . . ? C21 N3 C22 C27 -168.7(4) . . . . ? N3 C22 C27 C28 179.9(4) . . . . ? C22 C27 C28 C28 -179.9(5) . . . 2_575 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.600 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.084 data_lj-7 _database_code_depnum_ccdc_archive 'CCDC 909348' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cu N3 O8' _chemical_formula_weight 459.92 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 8.9363(10) _cell_length_b 10.1567(12) _cell_length_c 10.7519(12) _cell_angle_alpha 80.852(2) _cell_angle_beta 79.235(2) _cell_angle_gamma 74.262(2) _cell_volume 916.69(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1997 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 1.245 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5089 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_unetI/netI 0.0378 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3571 _reflns_number_gt 3063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0576P)^2^+1.5160P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3571 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.22646(5) 0.32205(4) 0.35388(4) 0.01868(14) Uani 1 1 d . . . O1 O 0.3376(3) 0.1294(2) 0.3466(2) 0.0250(5) Uani 1 1 d . . . N1 N 0.1981(3) 0.3511(3) 0.1666(3) 0.0221(6) Uani 1 1 d . . . C1 C 0.2786(6) 0.4233(6) 0.0776(4) 0.0530(13) Uani 1 1 d . . . H1A H 0.3465 0.4651 0.1033 0.064 Uiso 1 1 calc R . . O1W O -0.0517(3) 0.3791(3) 0.4128(3) 0.0376(6) Uani 1 1 d . . . H1WA H -0.0657 0.4494 0.3575 0.045 Uiso 1 1 d R . . H1WB H -0.0975 0.4048 0.4847 0.045 Uiso 1 1 d R . . N2 N 0.7725(3) -0.2894(3) 0.4508(3) 0.0213(6) Uani 1 1 d . . . H2B H 0.8026 -0.2214 0.4676 0.026 Uiso 1 1 calc R . . H2C H 0.8320 -0.3715 0.4589 0.026 Uiso 1 1 calc R . . O2 O 0.1270(3) 0.0506(3) 0.3532(3) 0.0388(7) Uani 1 1 d . . . C2 C 0.2673(6) 0.4397(7) -0.0499(4) 0.0620(16) Uani 1 1 d . . . H2A H 0.3263 0.4910 -0.1083 0.074 Uiso 1 1 calc R . . O2W O 0.7664(3) -0.7517(4) 0.3093(3) 0.0554(9) Uani 1 1 d . . . H2WA H 0.6757 -0.7425 0.3390 0.066 Uiso 1 1 d R . . H2WB H 0.8358 -0.7804 0.3361 0.066 Uiso 1 1 d R . . O3 O 0.2250(3) -0.4767(2) 0.3592(2) 0.0251(5) Uani 1 1 d . . . C3 C 0.1672(5) 0.3792(5) -0.0894(4) 0.0373(9) Uani 1 1 d . . . H3A H 0.1575 0.3883 -0.1751 0.045 Uiso 1 1 calc R . . N3 N -0.1805(8) 0.2456(8) 0.0520(6) 0.0345(11) Uani 0.505(6) 1 d P A 1 H3B H -0.1803 0.2604 0.1285 0.041 Uiso 0.505(6) 1 calc PR A 1 N3' N -0.1057(8) 0.1704(8) 0.0251(7) 0.0345(11) Uani 0.495(6) 1 d P A 2 H3'A H -0.1195 0.1806 0.1047 0.041 Uiso 0.495(6) 1 calc PR A 2 O3W O -0.1248(4) -0.0414(4) 0.3422(3) 0.0602(10) Uani 1 1 d . . . H3WA H -0.0743 -0.0782 0.2759 0.072 Uiso 1 1 d R . . H3WB H -0.0339 -0.0282 0.3706 0.072 Uiso 1 1 d R . . O4 O 0.4732(3) -0.5819(2) 0.2979(2) 0.0310(6) Uani 1 1 d . . . C4 C 0.0811(4) 0.3041(4) 0.0007(3) 0.0291(8) Uani 1 1 d . A . C5 C 0.1014(4) 0.2917(4) 0.1275(3) 0.0263(7) Uani 1 1 d . . . H5A H 0.0452 0.2398 0.1878 0.032 Uiso 1 1 calc R . . O5 O -0.0061(8) 0.2225(6) -0.1594(4) 0.121(2) Uani 1 1 d . A . C6 C -0.0266(8) 0.2392(6) -0.0461(5) 0.075(2) Uani 1 1 d . . . C7 C -0.3268(9) 0.2274(9) 0.0188(9) 0.0528(17) Uani 0.569(7) 1 d P A 1 H7A H -0.4148 0.2741 0.0768 0.063 Uiso 0.569(7) 1 calc PR A 1 H7B H -0.3385 0.2737 -0.0662 0.063 Uiso 0.569(7) 1 calc PR A 1 C7' C -0.1792(12) 0.0735(13) -0.0081(12) 0.0528(17) Uani 0.431(7) 1 d P A 2 H7'A H -0.1527 0.0721 -0.0997 0.063 Uiso 0.431(7) 1 calc PR A 2 H7'B H -0.1290 -0.0168 0.0305 0.063 Uiso 0.431(7) 1 calc PR A 2 C8 C -0.3391(5) 0.0883(5) 0.0219(5) 0.0483(11) Uani 1 1 d . . . H8A H -0.3181 0.0393 0.1044 0.058 Uiso 1 1 calc R A 1 H8B H -0.2571 0.0440 -0.0418 0.058 Uiso 1 1 calc R A 1 C9 C -0.4929(9) 0.0718(8) -0.0005(8) 0.0459(16) Uani 0.591(8) 1 d P . 1 H9A H -0.5145 0.1223 -0.0823 0.055 Uiso 0.591(8) 1 calc PR . 1 H9B H -0.5744 0.1152 0.0641 0.055 Uiso 0.591(8) 1 calc PR . 1 C9' C -0.4156(12) -0.0098(12) -0.0078(12) 0.0459(16) Uani 0.409(8) 1 d P . 2 H9'A H -0.3764 -0.0237 -0.0963 0.055 Uiso 0.409(8) 1 calc PR . 2 H9'B H -0.3754 -0.0964 0.0421 0.055 Uiso 0.409(8) 1 calc PR . 2 C10 C 0.2691(4) 0.0324(3) 0.3548(3) 0.0214(7) Uani 1 1 d . . . C11 C 0.3752(4) -0.1117(3) 0.3660(3) 0.0203(7) Uani 1 1 d . . . C12 C 0.3204(4) -0.2240(3) 0.3498(3) 0.0222(7) Uani 1 1 d . . . H12A H 0.2178 -0.2107 0.3349 0.027 Uiso 1 1 calc R . . C13 C 0.4211(4) -0.3553(3) 0.3561(3) 0.0206(7) Uani 1 1 d . . . C14 C 0.3708(4) -0.4794(3) 0.3356(3) 0.0221(7) Uani 1 1 d . . . C15 C 0.5719(4) -0.3762(3) 0.3855(3) 0.0201(7) Uani 1 1 d . . . H15A H 0.6389 -0.4641 0.3892 0.024 Uiso 1 1 calc R . . C16 C 0.6222(4) -0.2656(3) 0.4092(3) 0.0188(6) Uani 1 1 d . . . C17 C 0.5255(4) -0.1332(3) 0.3959(3) 0.0195(6) Uani 1 1 d . . . H17A H 0.5614 -0.0587 0.4071 0.023 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 Cu1 0.0237(2) 0.0139(2) 0.0213(2) -0.00392(14) -0.00801(15) -0.00527(15) O1 0.0301(13) 0.0139(11) 0.0341(14) -0.0041(10) -0.0109(10) -0.0058(10) N1 0.0201(14) 0.0245(15) 0.0234(15) -0.0065(11) -0.0042(11) -0.0056(11) C1 0.059(3) 0.090(4) 0.031(2) 0.004(2) -0.013(2) -0.055(3) O1W 0.0262(14) 0.0454(17) 0.0391(16) -0.0073(13) -0.0002(11) -0.0072(12) N2 0.0207(14) 0.0180(14) 0.0269(15) -0.0028(11) -0.0088(11) -0.0037(11) O2 0.0264(14) 0.0235(14) 0.067(2) -0.0001(13) -0.0153(13) -0.0045(11) C2 0.060(3) 0.116(5) 0.026(2) 0.006(2) -0.002(2) -0.060(3) O2W 0.0279(15) 0.070(2) 0.068(2) 0.0135(18) -0.0171(14) -0.0185(15) O3 0.0292(13) 0.0195(12) 0.0313(13) -0.0045(10) -0.0073(10) -0.0113(10) C3 0.037(2) 0.055(3) 0.0193(18) -0.0091(17) -0.0009(15) -0.0113(19) N3 0.032(3) 0.046(4) 0.034(3) -0.013(2) -0.007(2) -0.019(2) N3' 0.032(3) 0.046(4) 0.034(3) -0.013(2) -0.007(2) -0.019(2) O3W 0.054(2) 0.081(3) 0.061(2) 0.0155(18) -0.0220(16) -0.0466(19) O4 0.0362(14) 0.0201(13) 0.0413(15) -0.0126(11) -0.0120(11) -0.0052(11) C4 0.035(2) 0.032(2) 0.0245(18) -0.0087(15) -0.0099(15) -0.0076(16) C5 0.0298(18) 0.0272(19) 0.0249(18) -0.0024(14) -0.0080(14) -0.0101(15) O5 0.248(7) 0.133(4) 0.041(2) 0.015(2) -0.067(3) -0.133(5) C6 0.130(5) 0.087(4) 0.044(3) 0.019(3) -0.051(3) -0.079(4) C7 0.042(4) 0.058(4) 0.071(5) -0.029(4) -0.010(3) -0.020(3) C7' 0.042(4) 0.058(4) 0.071(5) -0.029(4) -0.010(3) -0.020(3) C8 0.041(2) 0.059(3) 0.056(3) -0.022(2) -0.007(2) -0.022(2) C9 0.030(4) 0.044(4) 0.069(4) -0.012(3) -0.016(3) -0.008(2) C9' 0.030(4) 0.044(4) 0.069(4) -0.012(3) -0.016(3) -0.008(2) C10 0.0265(17) 0.0173(16) 0.0222(16) -0.0033(12) -0.0068(13) -0.0056(13) C11 0.0229(16) 0.0182(16) 0.0217(16) -0.0037(13) -0.0048(13) -0.0067(13) C12 0.0223(16) 0.0187(16) 0.0288(18) -0.0020(13) -0.0090(13) -0.0074(13) C13 0.0282(17) 0.0164(16) 0.0201(16) -0.0025(12) -0.0059(13) -0.0087(13) C14 0.0320(18) 0.0161(16) 0.0220(17) 0.0016(13) -0.0130(14) -0.0086(14) C15 0.0247(16) 0.0143(15) 0.0215(16) -0.0044(12) -0.0066(13) -0.0017(13) C16 0.0193(15) 0.0219(16) 0.0169(15) -0.0026(12) -0.0039(12) -0.0071(13) C17 0.0257(16) 0.0166(15) 0.0199(16) -0.0031(12) -0.0062(12) -0.0088(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.946(2) . ? Cu1 N1 2.041(3) . ? Cu1 O3 2.051(2) 1_565 ? Cu1 N2 2.075(3) 2_656 ? Cu1 O1W 2.380(3) . ? O1 C10 1.277(4) . ? N1 C1 1.334(5) . ? N1 C5 1.336(4) . ? C1 C2 1.373(6) . ? N2 C16 1.441(4) . ? N2 Cu1 2.075(3) 2_656 ? O2 C10 1.235(4) . ? C2 C3 1.372(6) . ? O3 C14 1.274(4) . ? O3 Cu1 2.051(2) 1_545 ? C3 C4 1.384(5) . ? N3 C7 1.483(9) . ? N3 C6 1.562(9) . ? N3' C6 1.213(8) . ? N3' C7' 1.442(11) . ? O4 C14 1.251(4) . ? C4 C5 1.390(5) . ? C4 C6 1.498(5) . ? O5 C6 1.230(7) . ? C7 C8 1.441(9) . ? C7' C8 1.376(11) . ? C8 C9' 1.454(11) . ? C8 C9 1.496(8) . ? C9 C9 1.496(15) 2_455 ? C9' C9' 1.45(2) 2_455 ? C10 C11 1.514(5) . ? C11 C17 1.391(4) . ? C11 C12 1.403(4) . ? C12 C13 1.392(5) . ? C13 C15 1.394(4) . ? C13 C14 1.507(4) . ? C15 C16 1.391(4) . ? C16 C17 1.390(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 O1 Cu1 N1 92.96(11) . . ? O1 Cu1 O3 151.07(10) . 1_565 ? N1 Cu1 O3 94.11(10) . 1_565 ? O1 Cu1 N2 87.99(10) . 2_656 ? N1 Cu1 N2 172.99(10) . 2_656 ? O3 Cu1 N2 88.36(10) 1_565 2_656 ? O1 Cu1 O1W 118.74(10) . . ? N1 Cu1 O1W 89.56(10) . . ? O3 Cu1 O1W 89.35(10) 1_565 . ? N2 Cu1 O1W 83.90(10) 2_656 . ? C10 O1 Cu1 123.8(2) . . ? C1 N1 C5 117.0(3) . . ? C1 N1 Cu1 122.5(2) . . ? C5 N1 Cu1 120.4(2) . . ? N1 C1 C2 123.9(4) . . ? C16 N2 Cu1 116.5(2) . 2_656 ? C3 C2 C1 118.8(4) . . ? C14 O3 Cu1 102.5(2) . 1_545 ? C2 C3 C4 118.8(4) . . ? C7 N3 C6 122.9(6) . . ? C6 N3' C7' 127.5(8) . . ? C3 C4 C5 118.5(3) . . ? C3 C4 C6 117.2(4) . . ? C5 C4 C6 124.3(4) . . ? N1 C5 C4 123.0(3) . . ? N3' C6 O5 115.6(5) . . ? N3' C6 C4 122.2(5) . . ? O5 C6 C4 119.4(5) . . ? N3' C6 N3 35.7(4) . . ? O5 C6 N3 127.6(5) . . ? C4 C6 N3 110.1(4) . . ? C8 C7 N3 117.2(7) . . ? C8 C7' N3' 121.2(9) . . ? C7' C8 C7 78.0(6) . . ? C7' C8 C9' 122.2(7) . . ? C7 C8 C9' 150.9(7) . . ? C7' C8 C9 153.1(7) . . ? C7 C8 C9 116.5(6) . . ? C9' C8 C9 36.6(5) . . ? C8 C9 C9 117.2(8) . 2_455 ? C9' C9' C8 124.2(13) 2_455 . ? O2 C10 O1 124.3(3) . . ? O2 C10 C11 120.5(3) . . ? O1 C10 C11 115.2(3) . . ? C17 C11 C12 120.0(3) . . ? C17 C11 C10 119.9(3) . . ? C12 C11 C10 120.0(3) . . ? C13 C12 C11 119.3(3) . . ? C12 C13 C15 120.3(3) . . ? C12 C13 C14 121.9(3) . . ? C15 C13 C14 117.8(3) . . ? O4 C14 O3 122.3(3) . . ? O4 C14 C13 119.2(3) . . ? O3 C14 C13 118.5(3) . . ? C16 C15 C13 120.1(3) . . ? C17 C16 C15 119.8(3) . . ? C17 C16 N2 120.3(3) . . ? C15 C16 N2 119.9(3) . . ? C16 C17 C11 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.779 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.088