# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhengzhi Zeng' _publ_contact_author_email zengzhzh@yahoo.com.cn _publ_author_name 'Zhengzhi Zeng' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 829291' #TrackingRef '- P-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N3 O4' _chemical_formula_weight 379.41 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' _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 8.358(3) _cell_length_b 10.068(3) _cell_length_c 11.971(4) _cell_angle_alpha 89.947(3) _cell_angle_beta 85.210(3) _cell_angle_gamma 67.715(3) _cell_volume 928.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1462 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9793 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6727 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3404 _reflns_number_gt 1992 _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. ; _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^)+(0.0515P)^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 3404 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.5535(3) -0.6581(2) 0.6870(2) 0.0517(6) Uani 1 1 d . . . C2 C 0.6648(4) -0.7897(3) 0.6406(2) 0.0682(8) Uani 1 1 d . . . H2 H 0.6521 -0.8733 0.6648 0.082 Uiso 1 1 calc R . . C3 C 0.7934(3) -0.7977(3) 0.5596(2) 0.0692(8) Uani 1 1 d . . . H3 H 0.8685 -0.8869 0.5296 0.083 Uiso 1 1 calc R . . C4 C 0.8133(3) -0.6749(3) 0.5216(2) 0.0594(7) Uani 1 1 d . . . H4 H 0.9002 -0.6808 0.4657 0.071 Uiso 1 1 calc R . . C5 C 0.7028(3) -0.5437(2) 0.56764(18) 0.0489(6) Uani 1 1 d . . . H5 H 0.7167 -0.4610 0.5425 0.059 Uiso 1 1 calc R . . C6 C 0.5708(3) -0.5313(2) 0.65070(18) 0.0404(5) Uani 1 1 d . . . C7 C 0.4452(3) -0.3929(2) 0.70106(18) 0.0440(6) Uani 1 1 d . . . C8 C 0.3403(3) -0.0320(2) 0.64527(19) 0.0457(6) Uani 1 1 d . . . H8 H 0.4171 -0.0475 0.5813 0.055 Uiso 1 1 calc R . . C9 C 0.2260(3) 0.1140(2) 0.67977(18) 0.0405(5) Uani 1 1 d . . . C10 C 0.1224(3) 0.1507(2) 0.77745(17) 0.0412(5) Uani 1 1 d . . . H10 H 0.1200 0.0786 0.8254 0.049 Uiso 1 1 calc R . . C11 C 0.0184(2) 0.2945(2) 0.80840(17) 0.0385(5) Uani 1 1 d . . . C12 C 0.0264(2) 0.4013(2) 0.73616(17) 0.0394(5) Uani 1 1 d . . . C13 C 0.2262(3) 0.2247(2) 0.60304(19) 0.0452(6) Uani 1 1 d . . . C14 C -0.0916(3) 0.3426(2) 0.90749(18) 0.0464(6) Uani 1 1 d . . . H14 H -0.1021 0.2753 0.9578 0.056 Uiso 1 1 calc R . . C15 C -0.1835(3) 0.4849(2) 0.93245(18) 0.0477(6) Uani 1 1 d . . . H15 H -0.2560 0.5125 0.9987 0.057 Uiso 1 1 calc R . . C16 C -0.1701(3) 0.5917(2) 0.85887(18) 0.0417(5) Uani 1 1 d . . . C17 C -0.0612(3) 0.5449(2) 0.75891(18) 0.0448(6) Uani 1 1 d . . . H17 H -0.0489 0.6114 0.7085 0.054 Uiso 1 1 calc R . . C18 C -0.3669(3) 0.7852(2) 0.98985(18) 0.0512(6) Uani 1 1 d . . . H18A H -0.3721 0.8806 1.0085 0.061 Uiso 1 1 calc R . . H18B H -0.3120 0.7222 1.0487 0.061 Uiso 1 1 calc R . . C19 C -0.5502(3) 0.7906(3) 0.9869(2) 0.0658(7) Uani 1 1 d . . . H19A H -0.6071 0.8557 0.9309 0.099 Uiso 1 1 calc R . . H19B H -0.6132 0.8232 1.0589 0.099 Uiso 1 1 calc R . . H19C H -0.5463 0.6964 0.9691 0.099 Uiso 1 1 calc R . . C20 C -0.2523(3) 0.8444(2) 0.80681(19) 0.0504(6) Uani 1 1 d . . . H20A H -0.3585 0.9290 0.8196 0.060 Uiso 1 1 calc R . . H20B H -0.2454 0.8093 0.7304 0.060 Uiso 1 1 calc R . . C21 C -0.0983(3) 0.8866(3) 0.8198(2) 0.0700(8) Uani 1 1 d . . . H21A H -0.1058 0.9238 0.8947 0.105 Uiso 1 1 calc R . . H21B H -0.0992 0.9589 0.7672 0.105 Uiso 1 1 calc R . . H21C H 0.0075 0.8038 0.8058 0.105 Uiso 1 1 calc R . . N1 N 0.4562(2) -0.27147(18) 0.66046(16) 0.0448(5) Uani 1 1 d . . . N2 N 0.3375(2) -0.13922(18) 0.70067(15) 0.0452(5) Uani 1 1 d . . . N4 N -0.2602(2) 0.73442(18) 0.88377(15) 0.0470(5) Uani 1 1 d . . . O1 O 0.4285(2) -0.65699(17) 0.76601(16) 0.0744(6) Uani 1 1 d . . . H1 H 0.3785 -0.5755 0.7933 0.112 Uiso 1 1 calc R . . O2 O 0.3327(2) -0.38796(16) 0.77680(13) 0.0642(5) Uani 1 1 d . . . O3 O 0.3046(2) 0.20616(15) 0.51005(13) 0.0609(5) Uani 1 1 d . . . O4 O 0.12759(17) 0.36459(14) 0.63508(11) 0.0466(4) Uani 1 1 d . . . H1N H 0.533(3) -0.272(2) 0.6032(18) 0.056(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0549(15) 0.0448(15) 0.0562(17) 0.0115(12) -0.0146(13) -0.0179(12) C2 0.0737(19) 0.0405(15) 0.088(2) 0.0141(14) -0.0241(17) -0.0159(14) C3 0.0666(19) 0.0412(15) 0.085(2) -0.0078(14) -0.0270(16) 0.0003(14) C4 0.0562(16) 0.0546(16) 0.0551(17) -0.0076(13) -0.0025(13) -0.0077(13) C5 0.0512(14) 0.0429(14) 0.0503(15) 0.0043(11) -0.0056(12) -0.0150(12) C6 0.0434(13) 0.0398(12) 0.0389(13) 0.0057(10) -0.0116(10) -0.0152(10) C7 0.0470(14) 0.0449(14) 0.0424(15) 0.0024(11) -0.0047(11) -0.0198(11) C8 0.0443(13) 0.0420(14) 0.0475(15) -0.0027(11) 0.0060(11) -0.0148(11) C9 0.0339(12) 0.0393(12) 0.0460(14) -0.0036(11) 0.0007(10) -0.0122(10) C10 0.0419(13) 0.0390(13) 0.0442(14) 0.0037(10) -0.0002(11) -0.0179(10) C11 0.0356(12) 0.0384(12) 0.0427(14) -0.0003(10) 0.0011(10) -0.0163(10) C12 0.0356(12) 0.0440(13) 0.0372(14) -0.0041(10) 0.0061(10) -0.0153(10) C13 0.0406(13) 0.0408(13) 0.0487(16) -0.0027(11) 0.0057(11) -0.0112(11) C14 0.0489(14) 0.0438(14) 0.0459(15) 0.0045(11) 0.0057(11) -0.0191(11) C15 0.0493(14) 0.0485(14) 0.0425(14) -0.0051(11) 0.0124(11) -0.0188(11) C16 0.0374(12) 0.0410(13) 0.0458(14) -0.0029(11) 0.0016(10) -0.0151(10) C17 0.0470(13) 0.0394(13) 0.0462(15) 0.0029(10) 0.0076(11) -0.0168(11) C18 0.0518(14) 0.0438(14) 0.0525(16) -0.0117(11) 0.0074(12) -0.0143(11) C19 0.0476(15) 0.0764(18) 0.0657(18) -0.0126(14) 0.0102(13) -0.0182(13) C20 0.0454(14) 0.0386(13) 0.0586(16) 0.0013(11) 0.0034(12) -0.0079(11) C21 0.0570(16) 0.0563(16) 0.096(2) 0.0142(15) -0.0004(15) -0.0218(13) N1 0.0447(12) 0.0369(11) 0.0482(13) -0.0004(9) 0.0055(10) -0.0125(9) N2 0.0419(11) 0.0385(11) 0.0494(12) -0.0050(9) 0.0020(9) -0.0101(9) N4 0.0493(11) 0.0377(11) 0.0471(12) -0.0031(9) 0.0130(9) -0.0123(9) O1 0.0833(14) 0.0653(12) 0.0803(14) 0.0246(11) -0.0008(11) -0.0360(11) O2 0.0648(11) 0.0602(11) 0.0652(12) 0.0013(9) 0.0192(9) -0.0262(9) O3 0.0634(11) 0.0509(10) 0.0545(11) -0.0026(8) 0.0237(9) -0.0121(8) O4 0.0478(9) 0.0395(9) 0.0447(10) -0.0007(7) 0.0140(7) -0.0114(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.346(3) . ? C1 C2 1.382(3) . ? C1 C6 1.403(3) . ? C2 C3 1.365(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 H5 0.9300 . ? C6 C7 1.481(3) . ? C7 O2 1.238(2) . ? C7 N1 1.347(3) . ? C8 N2 1.273(2) . ? C8 C9 1.454(3) . ? C8 H8 0.9300 . ? C9 C10 1.358(3) . ? C9 C13 1.444(3) . ? C10 C11 1.408(3) . ? C10 H10 0.9300 . ? C11 C12 1.397(3) . ? C11 C14 1.403(3) . ? C12 C17 1.366(3) . ? C12 O4 1.382(2) . ? C13 O3 1.220(2) . ? C13 O4 1.370(2) . ? C14 C15 1.364(3) . ? C14 H14 0.9300 . ? C15 C16 1.420(3) . ? C15 H15 0.9300 . ? C16 N4 1.365(2) . ? C16 C17 1.406(3) . ? C17 H17 0.9300 . ? C18 N4 1.462(2) . ? C18 C19 1.515(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.457(3) . ? C20 C21 1.520(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 N2 1.382(2) . ? N1 H1N 0.90(2) . ? O1 H1 0.8200 . ? 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 C2 117.6(2) . . ? O1 C1 C6 122.0(2) . . ? C2 C1 C6 120.3(2) . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.0(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 117.7(2) . . ? C5 C6 C7 124.16(19) . . ? C1 C6 C7 118.2(2) . . ? O2 C7 N1 120.8(2) . . ? O2 C7 C6 121.6(2) . . ? N1 C7 C6 117.57(19) . . ? N2 C8 C9 121.4(2) . . ? N2 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C13 119.40(19) . . ? C10 C9 C8 124.4(2) . . ? C13 C9 C8 116.21(19) . . ? C9 C10 C11 122.0(2) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C12 C11 C14 115.87(18) . . ? C12 C11 C10 118.05(19) . . ? C14 C11 C10 126.06(19) . . ? C17 C12 O4 115.95(18) . . ? C17 C12 C11 123.80(19) . . ? O4 C12 C11 120.25(18) . . ? O3 C13 O4 115.71(19) . . ? O3 C13 C9 126.2(2) . . ? O4 C13 C9 118.06(18) . . ? C15 C14 C11 122.1(2) . . ? C15 C14 H14 118.9 . . ? C11 C14 H14 118.9 . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? N4 C16 C17 121.16(19) . . ? N4 C16 C15 121.37(19) . . ? C17 C16 C15 117.47(19) . . ? C12 C17 C16 119.73(19) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N4 C18 C19 113.28(19) . . ? N4 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? N4 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 113.0(2) . . ? N4 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? N4 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C7 N1 N2 120.06(19) . . ? C7 N1 H1N 122.6(14) . . ? N2 N1 H1N 117.1(14) . . ? C8 N2 N1 115.44(18) . . ? C16 N4 C20 121.70(17) . . ? C16 N4 C18 121.85(18) . . ? C20 N4 C18 116.44(17) . . ? C1 O1 H1 109.5 . . ? C13 O4 C12 122.09(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.6(2) . . . . ? C6 C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 -178.3(2) . . . . ? O1 C1 C6 C5 -179.2(2) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? O1 C1 C6 C7 -0.7(3) . . . . ? C2 C1 C6 C7 178.5(2) . . . . ? C5 C6 C7 O2 -178.2(2) . . . . ? C1 C6 C7 O2 3.3(3) . . . . ? C5 C6 C7 N1 2.6(3) . . . . ? C1 C6 C7 N1 -175.84(19) . . . . ? N2 C8 C9 C10 7.4(3) . . . . ? N2 C8 C9 C13 -172.7(2) . . . . ? C13 C9 C10 C11 -2.1(3) . . . . ? C8 C9 C10 C11 177.84(19) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? C9 C10 C11 C14 -179.6(2) . . . . ? C14 C11 C12 C17 1.9(3) . . . . ? C10 C11 C12 C17 -176.72(19) . . . . ? C14 C11 C12 O4 -178.33(18) . . . . ? C10 C11 C12 O4 3.1(3) . . . . ? C10 C9 C13 O3 -175.4(2) . . . . ? C8 C9 C13 O3 4.7(3) . . . . ? C10 C9 C13 O4 3.4(3) . . . . ? C8 C9 C13 O4 -176.48(17) . . . . ? C12 C11 C14 C15 -0.7(3) . . . . ? C10 C11 C14 C15 177.7(2) . . . . ? C11 C14 C15 C16 -0.7(3) . . . . ? C14 C15 C16 N4 -179.30(19) . . . . ? C14 C15 C16 C17 1.1(3) . . . . ? O4 C12 C17 C16 178.68(18) . . . . ? C11 C12 C17 C16 -1.5(3) . . . . ? N4 C16 C17 C12 -179.64(19) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? O2 C7 N1 N2 -2.2(3) . . . . ? C6 C7 N1 N2 177.01(17) . . . . ? C9 C8 N2 N1 -178.22(17) . . . . ? C7 N1 N2 C8 -169.0(2) . . . . ? C17 C16 N4 C20 2.0(3) . . . . ? C15 C16 N4 C20 -177.65(19) . . . . ? C17 C16 N4 C18 -176.82(19) . . . . ? C15 C16 N4 C18 3.6(3) . . . . ? C21 C20 N4 C16 -85.2(3) . . . . ? C21 C20 N4 C18 93.6(2) . . . . ? C19 C18 N4 C16 -86.6(3) . . . . ? C19 C18 N4 C20 94.6(2) . . . . ? O3 C13 O4 C12 177.36(18) . . . . ? C9 C13 O4 C12 -1.6(3) . . . . ? C17 C12 O4 C13 178.13(18) . . . . ? C11 C12 O4 C13 -1.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.145 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049 # Attachment '- P21c.cif' data_p21c _database_code_depnum_ccdc_archive 'CCDC 829292' #TrackingRef '- P21c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 Cu N4 O9' _chemical_formula_weight 595.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.369(3) _cell_length_b 13.433(5) _cell_length_c 24.915(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.208(4) _cell_angle_gamma 90.00 _cell_volume 2800.8(19) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4683 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 24.01 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7416 _exptl_absorpt_correction_T_max 0.8848 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19770 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.49 _reflns_number_total 5186 _reflns_number_gt 3856 _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. ; _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^)+(0.0571P)^2^+13.5310P] 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 5186 _refine_ls_number_parameters 358 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2110 _refine_ls_wR_factor_gt 0.2003 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.160 _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 0.32121(9) 1.18973(6) 0.04739(3) 0.0398(3) Uani 1 1 d . . . C1 C 0.0057(7) 0.8854(5) 0.1286(2) 0.0382(14) Uani 1 1 d . . . C2 C -0.0738(8) 0.8560(5) 0.1729(3) 0.0462(16) Uani 1 1 d . . . H2 H -0.0815 0.8982 0.2024 0.055 Uiso 1 1 calc R . . C3 C -0.1449(8) 0.7609(5) 0.1742(2) 0.0451(16) Uani 1 1 d . . . C4 C -0.1311(8) 0.7013(5) 0.1276(3) 0.0484(16) Uani 1 1 d . . . H4 H -0.1771 0.6383 0.1273 0.058 Uiso 1 1 calc R . . C5 C -0.0535(8) 0.7331(5) 0.0836(3) 0.0468(16) Uani 1 1 d . . . H5 H -0.0494 0.6922 0.0535 0.056 Uiso 1 1 calc R . . C6 C 0.0229(7) 0.8284(5) 0.0820(2) 0.0401(14) Uani 1 1 d . . . C7 C 0.1124(7) 0.8665(5) 0.0401(2) 0.0390(14) Uani 1 1 d . . . H7 H 0.1270 0.8276 0.0096 0.047 Uiso 1 1 calc R . . C8 C 0.1805(7) 0.9597(4) 0.0418(2) 0.0345(13) Uani 1 1 d . . . C9 C 0.1595(7) 1.0182(5) 0.0895(2) 0.0378(14) Uani 1 1 d . . . C10 C 0.2682(7) 0.9966(5) -0.0025(2) 0.0398(14) Uani 1 1 d . . . H10 H 0.2847 0.9539 -0.0314 0.048 Uiso 1 1 calc R . . C11 C 0.4519(7) 1.2062(5) -0.0491(2) 0.0393(14) Uani 1 1 d . . . C12 C 0.5437(7) 1.2467(5) -0.0951(2) 0.0416(15) Uani 1 1 d . . . C13 C 0.5841(8) 1.1902(6) -0.1392(3) 0.0494(16) Uani 1 1 d . . . C14 C 0.6749(9) 1.2316(6) -0.1796(3) 0.0562(19) Uani 1 1 d . . . H14 H 0.7014 1.1936 -0.2095 0.067 Uiso 1 1 calc R . . C15 C 0.7268(10) 1.3289(7) -0.1760(3) 0.069(2) Uani 1 1 d . . . H15 H 0.7907 1.3556 -0.2029 0.083 Uiso 1 1 calc R . . C16 C 0.6837(9) 1.3865(6) -0.1326(3) 0.062(2) Uani 1 1 d . . . H16 H 0.7153 1.4528 -0.1305 0.074 Uiso 1 1 calc R . . C17 C 0.5941(9) 1.3450(6) -0.0927(3) 0.0549(18) Uani 1 1 d . . . H17 H 0.5661 1.3836 -0.0632 0.066 Uiso 1 1 calc R . . C18 C -0.3033(11) 0.6327(6) 0.2204(3) 0.071(2) Uani 1 1 d . . . H18A H -0.3514 0.6200 0.1856 0.085 Uiso 1 1 calc R . . H18B H -0.3887 0.6375 0.2465 0.085 Uiso 1 1 calc R . . C19 C -0.1970(16) 0.5472(8) 0.2350(4) 0.114(4) Uani 1 1 d . . . H19A H -0.0987 0.5521 0.2154 0.172 Uiso 1 1 calc R . . H19B H -0.2493 0.4858 0.2262 0.172 Uiso 1 1 calc R . . H19C H -0.1746 0.5490 0.2728 0.172 Uiso 1 1 calc R . . C20 C -0.2190(11) 0.7856(6) 0.2692(3) 0.065(2) Uani 1 1 d . . . H20A H -0.2334 0.7406 0.2992 0.078 Uiso 1 1 calc R . . H20B H -0.1160 0.8177 0.2736 0.078 Uiso 1 1 calc R . . C21 C -0.3450(12) 0.8621(7) 0.2708(3) 0.081(3) Uani 1 1 d . . . H21A H -0.3294 0.9085 0.2420 0.121 Uiso 1 1 calc R . . H21B H -0.3400 0.8967 0.3045 0.121 Uiso 1 1 calc R . . H21C H -0.4476 0.8309 0.2670 0.121 Uiso 1 1 calc R . . C22 C 0.5889(11) 1.1598(7) 0.1436(3) 0.071(2) Uani 1 1 d U . . H22A H 0.5167 1.1079 0.1554 0.085 Uiso 1 1 calc R . . H22B H 0.5593 1.2207 0.1620 0.085 Uiso 1 1 calc R . . C23 C 0.7482(15) 1.1333(12) 0.1593(4) 0.135(5) Uani 1 1 d U . . H23A H 0.7988 1.0977 0.1306 0.202 Uiso 1 1 calc R . . H23B H 0.7446 1.0920 0.1907 0.202 Uiso 1 1 calc R . . H23C H 0.8081 1.1926 0.1670 0.202 Uiso 1 1 calc R . . C24 C 0.6718(11) 0.4316(7) 0.0600(5) 0.090(3) Uani 1 1 d . . . H24A H 0.6710 0.4592 0.0960 0.108 Uiso 1 1 calc R . . H24B H 0.5625 0.4303 0.0469 0.108 Uiso 1 1 calc R . . C25 C 0.7693(12) 0.4961(7) 0.0247(4) 0.089(3) Uani 1 1 d . . . H25A H 0.8755 0.5016 0.0391 0.133 Uiso 1 1 calc R . . H25B H 0.7217 0.5610 0.0226 0.133 Uiso 1 1 calc R . . H25C H 0.7739 0.4675 -0.0106 0.133 Uiso 1 1 calc R . . N1 N -0.2175(8) 0.7265(5) 0.2186(2) 0.0571(16) Uani 1 1 d . . . N2 N 0.3265(6) 1.0849(4) -0.00570(19) 0.0355(11) Uani 1 1 d . . . N3 N 0.4074(6) 1.1116(4) -0.0519(2) 0.0414(12) Uani 1 1 d . . . N4 N 0.1342(7) 1.3321(4) 0.0886(2) 0.0459(13) Uani 1 1 d . . . O1 O 0.0733(5) 0.9800(3) 0.13044(17) 0.0458(11) Uani 1 1 d . . . O2 O 0.2112(6) 1.1028(3) 0.09855(17) 0.0496(12) Uani 1 1 d . . . O3 O 0.4199(5) 1.2631(3) -0.00952(17) 0.0452(11) Uani 1 1 d . . . O4 O 0.5453(7) 1.0930(4) -0.1444(2) 0.0655(14) Uani 1 1 d . . . H4A H 0.4787 1.0782 -0.1217 0.098 Uiso 1 1 calc R . . O5 O 0.2813(5) 1.3076(3) 0.09403(17) 0.0462(11) Uani 1 1 d . . . O6 O 0.0542(6) 1.2881(4) 0.0533(2) 0.0652(14) Uani 1 1 d . . . O7 O 0.0787(7) 1.3984(4) 0.1160(2) 0.0748(17) Uani 1 1 d . . . O8 O 0.5676(6) 1.1741(3) 0.08753(18) 0.0508(11) Uani 1 1 d . . . O9 O 0.7315(8) 0.3348(5) 0.0618(5) 0.136(4) Uani 1 1 d . . . H9 H 0.8260 0.3351 0.0533 0.204 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 0.0467(5) 0.0346(4) 0.0382(4) -0.0032(3) 0.0055(3) -0.0059(4) C1 0.036(3) 0.038(3) 0.040(3) 0.003(3) -0.003(3) -0.006(3) C2 0.048(4) 0.049(4) 0.041(3) -0.006(3) 0.007(3) -0.013(3) C3 0.045(4) 0.051(4) 0.040(3) 0.009(3) -0.003(3) -0.007(3) C4 0.056(4) 0.041(4) 0.048(4) 0.006(3) -0.002(3) -0.016(3) C5 0.054(4) 0.045(4) 0.041(3) -0.003(3) -0.005(3) -0.015(3) C6 0.040(3) 0.041(4) 0.040(3) 0.003(3) -0.006(3) -0.005(3) C7 0.044(4) 0.040(4) 0.033(3) -0.005(3) -0.002(3) -0.003(3) C8 0.035(3) 0.034(3) 0.035(3) -0.001(2) 0.001(2) -0.003(3) C9 0.038(3) 0.039(3) 0.037(3) 0.000(3) 0.007(3) -0.002(3) C10 0.048(4) 0.036(3) 0.035(3) -0.003(3) 0.001(3) 0.000(3) C11 0.038(3) 0.043(4) 0.038(3) 0.004(3) -0.002(3) 0.002(3) C12 0.040(3) 0.042(4) 0.043(3) 0.009(3) 0.004(3) 0.000(3) C13 0.045(4) 0.058(4) 0.045(4) 0.013(3) 0.002(3) -0.002(3) C14 0.059(5) 0.070(5) 0.040(4) 0.010(3) 0.002(3) -0.004(4) C15 0.057(5) 0.095(7) 0.056(5) 0.029(5) 0.002(4) -0.021(5) C16 0.064(5) 0.068(5) 0.054(4) 0.011(4) -0.004(4) -0.023(4) C17 0.059(5) 0.054(4) 0.051(4) 0.008(3) -0.002(3) -0.014(4) C18 0.083(6) 0.067(5) 0.062(5) 0.013(4) 0.010(4) -0.030(5) C19 0.162(12) 0.081(7) 0.100(8) 0.036(6) -0.027(8) -0.018(8) C20 0.079(6) 0.078(6) 0.038(4) 0.012(4) 0.005(4) -0.021(5) C21 0.090(7) 0.096(7) 0.056(5) -0.007(5) 0.014(5) -0.014(6) C22 0.080(6) 0.086(6) 0.047(4) -0.003(4) -0.002(4) 0.001(5) C23 0.114(9) 0.212(14) 0.078(7) 0.026(8) -0.024(6) 0.043(9) C24 0.068(6) 0.062(6) 0.139(9) 0.007(6) -0.007(6) -0.004(5) C25 0.089(7) 0.060(6) 0.118(8) -0.005(6) -0.019(6) -0.003(5) N1 0.070(4) 0.058(4) 0.044(3) 0.011(3) 0.005(3) -0.017(3) N2 0.036(3) 0.035(3) 0.035(3) 0.002(2) 0.003(2) -0.002(2) N3 0.047(3) 0.039(3) 0.038(3) 0.005(2) 0.009(2) -0.004(2) N4 0.048(3) 0.045(3) 0.044(3) -0.003(3) -0.001(3) 0.002(3) O1 0.056(3) 0.041(2) 0.040(2) -0.004(2) 0.011(2) -0.014(2) O2 0.064(3) 0.040(3) 0.045(3) -0.010(2) 0.015(2) -0.013(2) O3 0.057(3) 0.035(2) 0.043(2) -0.004(2) 0.004(2) -0.005(2) O4 0.088(4) 0.058(3) 0.051(3) -0.005(2) 0.020(3) -0.003(3) O5 0.048(3) 0.042(3) 0.049(3) -0.006(2) -0.002(2) -0.003(2) O6 0.054(3) 0.076(4) 0.066(3) -0.019(3) -0.013(3) 0.000(3) O7 0.073(4) 0.070(4) 0.081(4) -0.030(3) -0.001(3) 0.023(3) O8 0.053(3) 0.050(3) 0.049(3) 0.002(2) -0.001(2) 0.004(2) O9 0.053(4) 0.065(4) 0.290(12) 0.059(6) -0.023(6) -0.012(3) _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 1.917(4) . ? Cu1 N2 1.933(5) . ? Cu1 O2 1.961(4) . ? Cu1 O5 1.993(4) . ? Cu1 O8 2.298(5) . ? C1 C2 1.351(8) . ? C1 O1 1.392(7) . ? C1 C6 1.397(9) . ? C2 C3 1.410(9) . ? C2 H2 0.9300 . ? C3 N1 1.346(8) . ? C3 C4 1.417(9) . ? C4 C5 1.346(9) . ? C4 H4 0.9300 . ? C5 C6 1.432(9) . ? C5 H5 0.9300 . ? C6 C7 1.387(8) . ? C7 C8 1.376(8) . ? C7 H7 0.9300 . ? C8 C10 1.419(8) . ? C8 C9 1.435(8) . ? C9 O2 1.237(7) . ? C9 O1 1.353(7) . ? C10 N2 1.285(8) . ? C10 H10 0.9300 . ? C11 O3 1.277(7) . ? C11 N3 1.327(8) . ? C11 C12 1.485(8) . ? C12 C13 1.379(9) . ? C12 C17 1.387(9) . ? C13 O4 1.351(9) . ? C13 C14 1.381(9) . ? C14 C15 1.380(11) . ? C14 H14 0.9300 . ? C15 C16 1.380(11) . ? C15 H15 0.9300 . ? C16 C17 1.367(10) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N1 1.451(9) . ? C18 C19 1.497(13) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.473(12) . ? C20 N1 1.489(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O8 1.420(8) . ? C22 C23 1.433(13) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O9 1.394(11) . ? C24 C25 1.483(13) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N2 N3 1.385(6) . ? N4 O7 1.214(7) . ? N4 O6 1.252(7) . ? N4 O5 1.281(7) . ? O4 H4A 0.8200 . ? O9 H9 0.8200 . ? 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 N2 81.82(19) . . ? O3 Cu1 O2 172.73(18) . . ? N2 Cu1 O2 91.32(19) . . ? O3 Cu1 O5 95.53(18) . . ? N2 Cu1 O5 169.2(2) . . ? O2 Cu1 O5 90.77(18) . . ? O3 Cu1 O8 88.90(18) . . ? N2 Cu1 O8 102.03(19) . . ? O2 Cu1 O8 94.90(19) . . ? O5 Cu1 O8 88.34(18) . . ? C2 C1 O1 116.1(6) . . ? C2 C1 C6 124.8(6) . . ? O1 C1 C6 119.1(5) . . ? C1 C2 C3 119.5(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? N1 C3 C2 121.5(6) . . ? N1 C3 C4 121.2(6) . . ? C2 C3 C4 117.2(6) . . ? C5 C4 C3 122.0(6) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 121.5(6) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C1 118.7(6) . . ? C7 C6 C5 126.4(6) . . ? C1 C6 C5 114.9(6) . . ? C8 C7 C6 122.5(6) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C10 120.6(5) . . ? C7 C8 C9 118.2(5) . . ? C10 C8 C9 121.2(5) . . ? O2 C9 O1 113.4(5) . . ? O2 C9 C8 127.7(5) . . ? O1 C9 C8 119.0(5) . . ? N2 C10 C8 124.6(6) . . ? N2 C10 H10 117.7 . . ? C8 C10 H10 117.7 . . ? O3 C11 N3 123.7(5) . . ? O3 C11 C12 119.2(6) . . ? N3 C11 C12 117.1(5) . . ? C13 C12 C17 118.9(6) . . ? C13 C12 C11 122.9(6) . . ? C17 C12 C11 118.2(6) . . ? O4 C13 C12 123.2(6) . . ? O4 C13 C14 116.9(7) . . ? C12 C13 C14 119.8(7) . . ? C15 C14 C13 120.5(7) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.0(7) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.2(8) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C12 121.6(7) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? N1 C18 C19 112.3(8) . . ? N1 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? N1 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 N1 113.8(7) . . ? C21 C20 H20A 108.8 . . ? N1 C20 H20A 108.8 . . ? C21 C20 H20B 108.8 . . ? N1 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O8 C22 C23 114.5(8) . . ? O8 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? O8 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O9 C24 C25 111.5(9) . . ? O9 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? O9 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C3 N1 C18 123.3(6) . . ? C3 N1 C20 121.2(6) . . ? C18 N1 C20 115.5(6) . . ? C10 N2 N3 118.5(5) . . ? C10 N2 Cu1 128.4(4) . . ? N3 N2 Cu1 113.1(4) . . ? C11 N3 N2 110.0(5) . . ? O7 N4 O6 122.4(6) . . ? O7 N4 O5 119.9(6) . . ? O6 N4 O5 117.6(5) . . ? C9 O1 C1 122.5(5) . . ? C9 O2 Cu1 126.4(4) . . ? C11 O3 Cu1 110.8(4) . . ? C13 O4 H4A 109.5 . . ? N4 O5 Cu1 107.9(4) . . ? C22 O8 Cu1 123.3(5) . . ? C24 O9 H9 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.7(6) . . . . ? C6 C1 C2 C3 0.7(10) . . . . ? C1 C2 C3 N1 176.2(7) . . . . ? C1 C2 C3 C4 -1.2(10) . . . . ? N1 C3 C4 C5 -177.3(7) . . . . ? C2 C3 C4 C5 0.1(10) . . . . ? C3 C4 C5 C6 1.5(11) . . . . ? C2 C1 C6 C7 -177.8(6) . . . . ? O1 C1 C6 C7 2.6(9) . . . . ? C2 C1 C6 C5 0.8(10) . . . . ? O1 C1 C6 C5 -178.8(5) . . . . ? C4 C5 C6 C7 176.6(7) . . . . ? C4 C5 C6 C1 -1.9(10) . . . . ? C1 C6 C7 C8 -2.2(9) . . . . ? C5 C6 C7 C8 179.3(6) . . . . ? C6 C7 C8 C10 -178.6(6) . . . . ? C6 C7 C8 C9 1.1(9) . . . . ? C7 C8 C9 O2 180.0(6) . . . . ? C10 C8 C9 O2 -0.3(10) . . . . ? C7 C8 C9 O1 -0.4(9) . . . . ? C10 C8 C9 O1 179.2(6) . . . . ? C7 C8 C10 N2 175.2(6) . . . . ? C9 C8 C10 N2 -4.5(10) . . . . ? O3 C11 C12 C13 179.6(6) . . . . ? N3 C11 C12 C13 -0.6(9) . . . . ? O3 C11 C12 C17 1.3(9) . . . . ? N3 C11 C12 C17 -178.9(6) . . . . ? C17 C12 C13 O4 177.7(7) . . . . ? C11 C12 C13 O4 -0.6(11) . . . . ? C17 C12 C13 C14 0.7(10) . . . . ? C11 C12 C13 C14 -177.5(6) . . . . ? O4 C13 C14 C15 -176.6(7) . . . . ? C12 C13 C14 C15 0.6(11) . . . . ? C13 C14 C15 C16 -2.0(12) . . . . ? C14 C15 C16 C17 2.1(12) . . . . ? C15 C16 C17 C12 -0.8(12) . . . . ? C13 C12 C17 C16 -0.6(11) . . . . ? C11 C12 C17 C16 177.7(7) . . . . ? C2 C3 N1 C18 174.8(7) . . . . ? C4 C3 N1 C18 -7.9(11) . . . . ? C2 C3 N1 C20 -2.9(11) . . . . ? C4 C3 N1 C20 174.4(7) . . . . ? C19 C18 N1 C3 89.0(10) . . . . ? C19 C18 N1 C20 -93.2(9) . . . . ? C21 C20 N1 C3 82.6(9) . . . . ? C21 C20 N1 C18 -95.3(8) . . . . ? C8 C10 N2 N3 -178.9(6) . . . . ? C8 C10 N2 Cu1 2.4(9) . . . . ? O3 Cu1 N2 C10 -175.4(6) . . . . ? O2 Cu1 N2 C10 2.2(6) . . . . ? O5 Cu1 N2 C10 -98.9(11) . . . . ? O8 Cu1 N2 C10 97.5(5) . . . . ? O3 Cu1 N2 N3 5.8(4) . . . . ? O2 Cu1 N2 N3 -176.6(4) . . . . ? O5 Cu1 N2 N3 82.3(11) . . . . ? O8 Cu1 N2 N3 -81.3(4) . . . . ? O3 C11 N3 N2 -1.5(8) . . . . ? C12 C11 N3 N2 178.7(5) . . . . ? C10 N2 N3 C11 177.0(6) . . . . ? Cu1 N2 N3 C11 -4.1(6) . . . . ? O2 C9 O1 C1 -179.4(5) . . . . ? C8 C9 O1 C1 0.9(9) . . . . ? C2 C1 O1 C9 178.3(6) . . . . ? C6 C1 O1 C9 -2.0(9) . . . . ? O1 C9 O2 Cu1 -173.0(4) . . . . ? C8 C9 O2 Cu1 6.6(10) . . . . ? O3 Cu1 O2 C9 12.6(19) . . . . ? N2 Cu1 O2 C9 -6.5(6) . . . . ? O5 Cu1 O2 C9 162.9(6) . . . . ? O8 Cu1 O2 C9 -108.7(6) . . . . ? N3 C11 O3 Cu1 6.3(8) . . . . ? C12 C11 O3 Cu1 -173.9(4) . . . . ? N2 Cu1 O3 C11 -6.3(4) . . . . ? O2 Cu1 O3 C11 -25.7(18) . . . . ? O5 Cu1 O3 C11 -175.8(4) . . . . ? O8 Cu1 O3 C11 96.0(4) . . . . ? O7 N4 O5 Cu1 175.1(5) . . . . ? O6 N4 O5 Cu1 -7.4(7) . . . . ? O3 Cu1 O5 N4 100.7(4) . . . . ? N2 Cu1 O5 N4 25.5(12) . . . . ? O2 Cu1 O5 N4 -75.7(4) . . . . ? O8 Cu1 O5 N4 -170.5(4) . . . . ? C23 C22 O8 Cu1 168.9(8) . . . . ? O3 Cu1 O8 C22 154.6(6) . . . . ? N2 Cu1 O8 C22 -124.0(6) . . . . ? O2 Cu1 O8 C22 -31.6(6) . . . . ? O5 Cu1 O8 C22 59.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.463 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.091