# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'M. Fatima C. Guedes da Silva' _publ_contact_author_email fatima.guedes@ist.utl.pt loop_ _publ_author_name M.N.Kopylovich M.J.Gajewska K.T.Mahmudov M.V.Kirillova P.J.Figiel 'M.F.C.G.da Silva' B.Gil-Hernandez J.Sanchiz A.J.L.Pombeiro # Attachment '- Compound3_revised.cif' data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 853676' #TrackingRef '- Compound3_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 Cu2 N4 O12' _chemical_formula_sum 'C26 H28 Cu2 N4 O12' _chemical_formula_weight 715.60 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1371(14) _cell_length_b 9.2116(15) _cell_length_c 10.2632(17) _cell_angle_alpha 63.521(8) _cell_angle_beta 68.961(7) _cell_angle_gamma 72.657(7) _cell_volume 711.7(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2831 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.99 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 366 _exptl_absorpt_coefficient_mu 1.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7245 _exptl_absorpt_correction_T_max 0.8850 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8859 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0818 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 26.97 _reflns_number_total 2876 _reflns_number_gt 1902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0656P)^2^+0.4128P] 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 2876 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0526(4) 0.2137(5) 0.6071(4) 0.0183(9) Uani 1 1 d . . . C2 C 0.0948(4) 0.2663(5) 0.5716(4) 0.0178(9) Uani 1 1 d . . . C3 C 0.1058(4) 0.3661(5) 0.6340(5) 0.0206(9) Uani 1 1 d . . . H3 H 0.2048 0.3985 0.6097 0.025 Uiso 1 1 calc R . . C4 C -0.0261(4) 0.4202(5) 0.7320(5) 0.0209(9) Uani 1 1 d . . . H4 H -0.0190 0.4902 0.7742 0.025 Uiso 1 1 calc R . . C5 C -0.1717(4) 0.3677(5) 0.7674(4) 0.0195(9) Uani 1 1 d . . . C6 C -0.1823(4) 0.2656(5) 0.7073(4) 0.0194(9) Uani 1 1 d . . . H6 H -0.2805 0.2300 0.7350 0.023 Uiso 1 1 calc R . . C7 C -0.3138(4) 0.4245(5) 0.8710(5) 0.0220(9) Uani 1 1 d . . . C8 C 0.6294(4) 0.0050(6) 0.1817(5) 0.0256(10) Uani 1 1 d . . . H8A H 0.6004 -0.0573 0.1408 0.038 Uiso 1 1 calc R . . H8B H 0.7035 -0.0676 0.2428 0.038 Uiso 1 1 calc R . . H8C H 0.6802 0.0963 0.0984 0.038 Uiso 1 1 calc R . . C9 C 0.4839(4) 0.0708(5) 0.2773(4) 0.0198(9) Uani 1 1 d . . . C10 C 0.4839(4) 0.1779(5) 0.3421(4) 0.0197(9) Uani 1 1 d . . . C11 C 0.6310(4) 0.2336(5) 0.3210(5) 0.0256(10) Uani 1 1 d . . . C20 C 0.1356(5) 0.2168(7) 0.0617(5) 0.0450(14) Uani 1 1 d . . . H20A H 0.2497 0.1792 0.0532 0.067 Uiso 1 1 calc R . . H20B H 0.1187 0.3275 -0.0150 0.067 Uiso 1 1 calc R . . H20C H 0.0933 0.1414 0.0462 0.067 Uiso 1 1 calc R . . C111 C 0.6200(5) 0.3556(6) 0.3844(6) 0.0335(11) Uani 1 1 d . . . H11A H 0.7265 0.3779 0.3624 0.050 Uiso 1 1 calc R . . H11B H 0.5740 0.3109 0.4939 0.050 Uiso 1 1 calc R . . H11C H 0.5521 0.4579 0.3384 0.050 Uiso 1 1 calc R . . N1 N 0.2190(3) 0.2048(4) 0.4690(4) 0.0163(7) Uani 1 1 d . . . N2 N 0.3563(3) 0.2400(4) 0.4353(4) 0.0174(7) Uani 1 1 d . . . O1 O -0.0574(3) 0.1237(4) 0.5385(3) 0.0236(7) Uani 1 1 d . . . O2 O 0.3593(3) 0.0188(4) 0.2987(3) 0.0247(7) Uani 1 1 d . . . O3 O 0.7591(3) 0.1813(4) 0.2528(4) 0.0443(9) Uani 1 1 d . . . O4 O -0.4430(3) 0.3810(4) 0.9025(3) 0.0278(7) Uani 1 1 d . . . O5 O -0.2952(3) 0.5218(4) 0.9214(3) 0.0300(7) Uani 1 1 d . . . H5 H -0.3786 0.5390 0.9861 0.045 Uiso 1 1 calc R . . O20 O 0.0564(3) 0.2203(4) 0.2068(3) 0.0295(7) Uani 1 1 d D . . Cu1 Cu 0.14847(5) 0.07523(7) 0.40761(6) 0.0244(2) Uani 1 1 d . . . H20O H -0.043(2) 0.221(5) 0.228(5) 0.029 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0129(18) 0.023(2) 0.023(2) -0.013(2) -0.0022(16) -0.0051(15) C2 0.0089(17) 0.023(2) 0.022(2) -0.011(2) -0.0024(15) -0.0022(15) C3 0.0144(18) 0.027(2) 0.027(2) -0.014(2) -0.0060(16) -0.0057(16) C4 0.0182(19) 0.025(2) 0.030(2) -0.017(2) -0.0101(17) -0.0021(16) C5 0.0162(19) 0.023(2) 0.020(2) -0.014(2) -0.0031(16) 0.0019(16) C6 0.0120(17) 0.023(2) 0.027(2) -0.015(2) -0.0028(16) -0.0027(15) C7 0.023(2) 0.024(2) 0.022(2) -0.014(2) -0.0051(17) -0.0002(17) C8 0.0127(19) 0.039(3) 0.034(3) -0.025(2) -0.0001(17) -0.0049(17) C9 0.0104(17) 0.025(2) 0.021(2) -0.009(2) -0.0041(15) 0.0000(15) C10 0.0132(18) 0.026(2) 0.024(2) -0.012(2) -0.0057(16) -0.0045(16) C11 0.016(2) 0.031(3) 0.032(3) -0.011(2) -0.0073(18) -0.0074(17) C20 0.029(3) 0.078(4) 0.034(3) -0.029(3) -0.003(2) -0.010(2) C111 0.020(2) 0.042(3) 0.050(3) -0.026(3) -0.007(2) -0.0095(19) N1 0.0088(14) 0.0222(18) 0.0219(19) -0.0135(17) -0.0023(13) -0.0021(12) N2 0.0122(15) 0.0192(17) 0.0248(19) -0.0121(16) -0.0053(13) -0.0016(13) O1 0.0133(13) 0.0361(17) 0.0346(17) -0.0290(16) 0.0032(11) -0.0088(12) O2 0.0148(13) 0.0330(17) 0.0372(18) -0.0252(16) -0.0018(12) -0.0061(12) O3 0.0105(15) 0.068(2) 0.073(3) -0.052(2) 0.0053(15) -0.0114(15) O4 0.0161(14) 0.0364(18) 0.0366(18) -0.0258(16) 0.0029(12) -0.0051(12) O5 0.0192(14) 0.0445(19) 0.0390(19) -0.0351(17) 0.0016(13) -0.0036(13) O20 0.0123(13) 0.048(2) 0.0328(18) -0.0219(17) -0.0010(12) -0.0061(13) Cu1 0.0094(2) 0.0377(3) 0.0380(4) -0.0295(3) 0.0014(2) -0.00551(19) _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. All H-atoms were introduced in calculated positions and refined on a riding model, except H20O (the hydroxyl H-atom from coordinated methanol) which was located in difference map positions and refined positionally with DFIX restraints, and with Uiso = 1.2Ueq of its parent O-atom. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.323(5) . ? C1 C6 1.384(5) . ? C1 C2 1.436(5) . ? C2 C3 1.374(5) . ? C2 N1 1.418(5) . ? C3 C4 1.390(5) . ? C3 H3 0.9500 . ? C4 C5 1.420(5) . ? C4 H4 0.9500 . ? C5 C6 1.374(6) . ? C5 C7 1.480(5) . ? C6 H6 0.9500 . ? C7 O4 1.245(5) . ? C7 O5 1.291(5) . ? C8 C9 1.487(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O2 1.275(4) . ? C9 C10 1.415(6) . ? C10 N2 1.375(5) . ? C10 C11 1.490(5) . ? C11 O3 1.212(5) . ? C11 C111 1.494(6) . ? C20 O20 1.414(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C111 H11A 0.9800 . ? C111 H11B 0.9800 . ? C111 H11C 0.9800 . ? N1 N2 1.277(4) . ? N1 Cu1 1.912(3) . ? O1 Cu1 1.939(2) . ? O1 Cu1 2.007(3) 2_556 ? O2 Cu1 1.899(3) . ? O5 H5 0.8400 . ? O20 Cu1 2.204(3) . ? O20 H20O 0.858(19) . ? Cu1 O1 2.007(3) 2_556 ? Cu1 Cu1 3.0137(10) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 124.2(3) . . ? O1 C1 C2 118.1(3) . . ? C6 C1 C2 117.6(4) . . ? C3 C2 N1 126.5(3) . . ? C3 C2 C1 121.0(3) . . ? N1 C2 C1 112.5(4) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 118.1(4) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 121.2(3) . . ? C6 C5 C7 119.9(4) . . ? C4 C5 C7 118.9(4) . . ? C5 C6 C1 121.3(4) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O4 C7 O5 123.6(4) . . ? O4 C7 C5 120.0(4) . . ? O5 C7 C5 116.3(3) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C10 122.8(3) . . ? O2 C9 C8 113.9(4) . . ? C10 C9 C8 123.3(3) . . ? N2 C10 C9 127.0(3) . . ? N2 C10 C11 110.4(4) . . ? C9 C10 C11 122.6(4) . . ? O3 C11 C10 120.7(4) . . ? O3 C11 C111 119.8(4) . . ? C10 C11 C111 119.5(4) . . ? O20 C20 H20A 109.5 . . ? O20 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O20 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 C111 H11A 109.5 . . ? C11 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? C11 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? N2 N1 C2 117.0(3) . . ? N2 N1 Cu1 130.9(3) . . ? C2 N1 Cu1 112.1(2) . . ? N1 N2 C10 120.1(3) . . ? C1 O1 Cu1 111.9(2) . . ? C1 O1 Cu1 137.8(2) . 2_556 ? Cu1 O1 Cu1 99.55(12) . 2_556 ? C9 O2 Cu1 128.0(3) . . ? C7 O5 H5 109.5 . . ? C20 O20 Cu1 124.7(3) . . ? C20 O20 H20O 111(3) . . ? Cu1 O20 H20O 112(3) . . ? O2 Cu1 N1 90.96(12) . . ? O2 Cu1 O1 173.52(12) . . ? N1 Cu1 O1 85.24(12) . . ? O2 Cu1 O1 100.44(11) . 2_556 ? N1 Cu1 O1 149.36(13) . 2_556 ? O1 Cu1 O1 80.45(12) . 2_556 ? O2 Cu1 O20 95.34(11) . . ? N1 Cu1 O20 113.43(13) . . ? O1 Cu1 O20 90.99(11) . . ? O1 Cu1 O20 93.88(12) 2_556 . ? O2 Cu1 Cu1 139.47(9) . 2_556 ? N1 Cu1 Cu1 121.31(9) . 2_556 ? O1 Cu1 Cu1 41.06(8) . 2_556 ? O1 Cu1 Cu1 39.39(7) 2_556 2_556 ? O20 Cu1 Cu1 93.22(7) . 2_556 ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.472 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.096 data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 866372' #TrackingRef '- Compound2_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H38 Cu2 N6 O14' _chemical_formula_sum 'C30 H38 Cu2 N6 O14' _chemical_formula_weight 833.74 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6358(2) _cell_length_b 10.3215(2) _cell_length_c 10.8552(3) _cell_angle_alpha 85.8940(10) _cell_angle_beta 71.985(2) _cell_angle_gamma 66.5280(10) _cell_volume 842.52(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9920 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 35.43 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 1.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6812 _exptl_absorpt_correction_T_max 0.8241 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15771 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3088 _reflns_number_gt 2867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All H-atoms were introduced in calculated positions and refined on a riding model, except H10A and H10B (the aqua H-atoms) which were located in difference map positions and refined positionally with DFIX restraints, and with Uiso = 1.5Ueq of their parent O-atom. ; _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^)+(0.0371P)^2^+1.0599P] 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 3088 _refine_ls_number_parameters 246 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1065(3) 0.6959(2) 0.27464(19) 0.0141(4) Uani 1 1 d . . . C2 C -0.0256(3) 0.6596(2) 0.13969(19) 0.0138(4) Uani 1 1 d . . . C3 C -0.1063(3) 0.7339(2) 0.04881(19) 0.0154(4) Uani 1 1 d . . . H3 H -0.0499 0.7073 -0.0411 0.018 Uiso 1 1 calc R . . C4 C -0.2687(3) 0.8464(2) 0.09003(19) 0.0151(4) Uani 1 1 d . . . H4 H -0.3276 0.8947 0.0291 0.018 Uiso 1 1 calc R . . C5 C -0.3464(3) 0.8891(2) 0.22268(19) 0.0138(4) Uani 1 1 d . . . C6 C -0.2660(3) 0.8155(2) 0.31405(19) 0.0148(4) Uani 1 1 d . . . H6 H -0.3194 0.8465 0.4032 0.018 Uiso 1 1 calc R . . C7 C -0.5134(3) 1.0174(2) 0.26798(19) 0.0157(4) Uani 1 1 d . . . C8 C 0.3750(3) 0.5034(2) -0.2714(2) 0.0243(5) Uani 1 1 d . . . H8A H 0.4414 0.4788 -0.3636 0.036 Uiso 1 1 calc R . . H8B H 0.3489 0.6024 -0.2513 0.036 Uiso 1 1 calc R . . H8C H 0.2636 0.4904 -0.2521 0.036 Uiso 1 1 calc R . . C9 C 0.4844(3) 0.4088(2) -0.1902(2) 0.0191(4) Uani 1 1 d . . . C10 C 0.3982(3) 0.4140(2) -0.04856(19) 0.0149(4) Uani 1 1 d . . . C11 C 0.4862(3) 0.3206(2) 0.03613(19) 0.0149(4) Uani 1 1 d . . . C12 C -0.0378(3) 0.2547(2) 0.3728(2) 0.0210(5) Uani 1 1 d . . . H12 H -0.0870 0.3175 0.4476 0.025 Uiso 1 1 calc R . . C13 C -0.0358(4) 0.0573(3) 0.2620(2) 0.0366(6) Uani 1 1 d . . . H13A H -0.1369 0.0543 0.2410 0.055 Uiso 1 1 calc R . . H13B H 0.0360 -0.0372 0.2828 0.055 Uiso 1 1 calc R . . H13C H 0.0369 0.0881 0.1872 0.055 Uiso 1 1 calc R . . C14 C -0.2385(4) 0.1430(3) 0.4855(3) 0.0413(7) Uani 1 1 d . . . H14A H -0.1955 0.0474 0.5161 0.062 Uiso 1 1 calc R . . H14B H -0.3443 0.1600 0.4602 0.062 Uiso 1 1 calc R . . H14C H -0.2685 0.2124 0.5551 0.062 Uiso 1 1 calc R . . C111 C 0.6641(3) 0.2015(2) -0.0151(2) 0.0197(4) Uani 1 1 d . . . H11A H 0.6971 0.1466 0.0569 0.029 Uiso 1 1 calc R . . H11B H 0.7528 0.2400 -0.0588 0.029 Uiso 1 1 calc R . . H11C H 0.6587 0.1401 -0.0771 0.029 Uiso 1 1 calc R . . N1 N 0.1400(2) 0.54399(17) 0.11084(16) 0.0136(3) Uani 1 1 d . . . N2 N 0.2335(2) 0.51794(17) -0.00979(16) 0.0143(3) Uani 1 1 d . . . N3 N -0.1004(2) 0.1568(2) 0.37364(18) 0.0230(4) Uani 1 1 d . . . O1 O -0.02779(18) 0.61534(15) 0.35822(13) 0.0176(3) Uani 1 1 d . . . O2 O 0.6410(2) 0.33540(19) -0.24215(15) 0.0307(4) Uani 1 1 d . . . O3 O 0.41837(18) 0.33074(14) 0.15846(13) 0.0174(3) Uani 1 1 d . . . O4 O -0.5544(2) 1.08764(15) 0.36706(14) 0.0232(3) Uani 1 1 d . . . O5 O -0.61339(19) 1.04768(15) 0.19004(14) 0.0200(3) Uani 1 1 d . . . H5 H -0.7055 1.1209 0.2200 0.030 Uiso 1 1 calc R . . O6 O 0.08121(18) 0.27067(15) 0.28105(15) 0.0209(3) Uani 1 1 d . . . O10 O 0.26396(19) 0.38474(16) 0.41931(14) 0.0181(3) Uani 1 1 d D . . Cu1 Cu 0.19350(3) 0.46482(2) 0.26513(2) 0.01524(9) Uani 1 1 d . . . H10A H 0.186(3) 0.390(3) 0.4846(19) 0.023 Uiso 1 1 d D . . H10B H 0.319(3) 0.3011(18) 0.401(2) 0.023 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0155(9) 0.0129(9) 0.0133(10) 0.0016(7) -0.0039(8) -0.0055(8) C2 0.0144(9) 0.0115(9) 0.0141(10) -0.0002(7) -0.0019(8) -0.0055(8) C3 0.0181(10) 0.0162(9) 0.0109(9) -0.0008(7) -0.0023(8) -0.0072(8) C4 0.0183(10) 0.0145(9) 0.0142(10) 0.0023(8) -0.0072(8) -0.0067(8) C5 0.0139(9) 0.0118(9) 0.0147(10) 0.0004(7) -0.0029(8) -0.0052(8) C6 0.0165(10) 0.0143(9) 0.0110(9) 0.0000(7) -0.0013(8) -0.0056(8) C7 0.0168(10) 0.0133(9) 0.0154(10) 0.0039(8) -0.0038(8) -0.0058(8) C8 0.0224(11) 0.0316(12) 0.0137(10) 0.0007(9) -0.0022(8) -0.0079(10) C9 0.0192(11) 0.0204(10) 0.0162(10) -0.0028(8) -0.0014(8) -0.0085(9) C10 0.0150(9) 0.0142(9) 0.0151(10) -0.0024(8) -0.0013(8) -0.0074(8) C11 0.0152(10) 0.0127(9) 0.0172(10) -0.0018(8) -0.0015(8) -0.0080(8) C12 0.0150(10) 0.0208(11) 0.0228(11) -0.0026(9) -0.0074(9) -0.0008(9) C13 0.0467(16) 0.0441(15) 0.0266(13) -0.0072(11) -0.0011(11) -0.0316(13) C14 0.0381(15) 0.0602(18) 0.0257(13) -0.0005(12) 0.0047(11) -0.0298(14) C111 0.0164(10) 0.0158(10) 0.0207(11) -0.0004(8) -0.0013(8) -0.0033(8) N1 0.0138(8) 0.0127(8) 0.0123(8) 0.0000(6) -0.0017(7) -0.0048(7) N2 0.0158(8) 0.0137(8) 0.0131(8) -0.0015(6) -0.0017(7) -0.0072(7) N3 0.0209(9) 0.0288(10) 0.0185(9) -0.0010(8) -0.0023(7) -0.0115(8) O1 0.0165(7) 0.0172(7) 0.0112(7) 0.0023(5) -0.0022(6) -0.0005(6) O2 0.0194(8) 0.0394(10) 0.0178(8) -0.0013(7) 0.0023(6) -0.0016(7) O3 0.0167(7) 0.0155(7) 0.0144(7) 0.0009(6) -0.0017(6) -0.0031(6) O4 0.0267(8) 0.0170(7) 0.0144(7) -0.0022(6) -0.0065(6) 0.0034(6) O5 0.0160(7) 0.0172(7) 0.0229(8) -0.0024(6) -0.0086(6) -0.0001(6) O6 0.0152(7) 0.0189(7) 0.0260(8) 0.0003(6) -0.0052(6) -0.0047(6) O10 0.0166(7) 0.0176(7) 0.0133(7) 0.0017(6) -0.0020(6) -0.0019(6) Cu1 0.01386(14) 0.01441(14) 0.01138(14) 0.00133(9) -0.00177(10) -0.00118(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.342(2) . ? C1 C6 1.400(3) . ? C1 C2 1.418(3) . ? C2 C3 1.392(3) . ? C2 N1 1.409(3) . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.405(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 C7 1.486(3) . ? C6 H6 0.9500 . ? C7 O4 1.216(2) . ? C7 O5 1.326(2) . ? C8 C9 1.511(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 O2 1.222(3) . ? C9 C10 1.481(3) . ? C10 N2 1.353(3) . ? C10 C11 1.440(3) . ? C11 O3 1.268(2) . ? C11 C111 1.499(3) . ? C12 O6 1.247(3) . ? C12 N3 1.320(3) . ? C12 H12 0.9500 . ? C13 N3 1.463(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N3 1.460(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C111 H11A 0.9800 . ? C111 H11B 0.9800 . ? C111 H11C 0.9800 . ? N1 N2 1.289(2) . ? N1 Cu1 1.9151(16) . ? O1 Cu1 1.9370(14) . ? O3 Cu1 1.9300(14) . ? O5 H5 0.8400 . ? O10 Cu1 1.9713(14) . ? O10 H10A 0.802(17) . ? O10 H10B 0.807(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 123.10(17) . . ? O1 C1 C2 119.07(17) . . ? C6 C1 C2 117.83(18) . . ? C3 C2 N1 125.42(18) . . ? C3 C2 C1 121.67(18) . . ? N1 C2 C1 112.91(17) . . ? C4 C3 C2 119.63(18) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.57(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 121.01(18) . . ? C6 C5 C7 118.45(17) . . ? C4 C5 C7 120.50(17) . . ? C5 C6 C1 120.08(18) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O4 C7 O5 123.27(18) . . ? O4 C7 C5 123.26(18) . . ? O5 C7 C5 113.48(17) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 C10 122.57(19) . . ? O2 C9 C8 119.34(19) . . ? C10 C9 C8 118.03(18) . . ? N2 C10 C11 125.14(18) . . ? N2 C10 C9 112.36(17) . . ? C11 C10 C9 122.47(18) . . ? O3 C11 C10 122.93(18) . . ? O3 C11 C111 115.09(18) . . ? C10 C11 C111 121.96(18) . . ? O6 C12 N3 124.8(2) . . ? O6 C12 H12 117.6 . . ? N3 C12 H12 117.6 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C111 H11A 109.5 . . ? C11 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? C11 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? N2 N1 C2 116.46(16) . . ? N2 N1 Cu1 131.54(13) . . ? C2 N1 Cu1 111.69(13) . . ? N1 N2 C10 121.76(17) . . ? C12 N3 C14 121.8(2) . . ? C12 N3 C13 121.62(19) . . ? C14 N3 C13 116.6(2) . . ? C1 O1 Cu1 110.34(12) . . ? C11 O3 Cu1 129.27(13) . . ? C7 O5 H5 109.5 . . ? Cu1 O10 H10A 116.9(18) . . ? Cu1 O10 H10B 105.3(18) . . ? H10A O10 H10B 105(3) . . ? N1 Cu1 O3 89.13(6) . . ? N1 Cu1 O1 85.83(6) . . ? O3 Cu1 O1 173.42(6) . . ? N1 Cu1 O10 176.12(6) . . ? O3 Cu1 O10 88.45(6) . . ? O1 Cu1 O10 96.35(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O6 0.84 1.83 2.666(2) 174.0 1_465 O10 H10A O1 0.802(17) 1.837(17) 2.636(2) 173(3) 2_566 O10 H10B O4 0.807(17) 2.033(17) 2.838(2) 176(3) 1_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.394 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.062