# 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 ? loop_ _publ_author_name F.Dimiza S.Fountoulaki A.N.Papadopoulos C.A.Kontogiorgis ; V.Tangoulis ; C.P.Raptopoulou V.Psycharis A.Terzis D.P.Kessissoglou ; G.Psomas ; _publ_contact_author_name 'George Psomas' _publ_contact_author_email gepsomas@chem.auth.gr data_psfd426 _database_code_depnum_ccdc_archive 'CCDC 797033' #TrackingRef '- psfd426.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H36 Cu N4 O4' _chemical_formula_weight 700.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 7.69410(10) _cell_length_b 26.6993(5) _cell_length_c 16.9080(3) _cell_angle_alpha 90.0000(10) _cell_angle_beta 97.7560(10) _cell_angle_gamma 90.00 _cell_volume 3441.59(10) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 28544 _cell_measurement_theta_min 6.63 _cell_measurement_theta_max 71.98 _exptl_crystal_description parall _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1460 _exptl_absorpt_coefficient_mu 1.278 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrystalClear, Rigaku MSC, 2005' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS SPIDER IPDS' _diffrn_measurement_method '\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33244 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 6.63 _diffrn_reflns_theta_max 64.99 _reflns_number_total 5823 _reflns_number_gt 4970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, Rigaku MSC, 2005' _computing_cell_refinement 'CrystalClear, Rigaku MSC, 2005' _computing_data_reduction 'CrystalClear, Rigaku MSC, 2005' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+1.4328P] 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 5823 _refine_ls_number_parameters 564 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.71544(4) 0.209876(12) 0.323395(18) 0.03731(13) Uani 1 1 d . . . N1 N 0.4465(3) 0.11599(8) 0.11496(13) 0.0496(5) Uani 1 1 d . . . O1 O 0.8094(2) 0.12366(6) 0.32271(9) 0.0449(4) Uani 1 1 d . . . O2 O 0.6434(2) 0.16637(6) 0.22991(9) 0.0476(4) Uani 1 1 d . . . C1 C 0.7130(3) 0.12460(8) 0.25741(13) 0.0384(5) Uani 1 1 d . . . C2 C 0.6735(3) 0.07790(8) 0.21038(13) 0.0377(5) Uani 1 1 d . . . C3 C 0.7672(3) 0.03485(10) 0.23643(15) 0.0470(6) Uani 1 1 d . . . C4 C 0.7389(4) -0.01032(11) 0.19802(17) 0.0573(7) Uani 1 1 d . . . C5 C 0.6123(4) -0.01302(10) 0.13190(17) 0.0577(7) Uani 1 1 d . . . C6 C 0.5169(4) 0.02831(9) 0.10448(16) 0.0497(6) Uani 1 1 d . . . C7 C 0.5447(3) 0.07480(8) 0.14280(13) 0.0401(5) Uani 1 1 d . . . C8 C 0.3223(3) 0.11580(9) 0.04443(14) 0.0437(5) Uani 1 1 d . . . C9 C 0.3647(4) 0.13893(10) -0.02362(16) 0.0516(6) Uani 1 1 d . . . C10 C 0.2425(5) 0.13955(12) -0.09263(17) 0.0620(8) Uani 1 1 d . . . C11 C 0.0843(4) 0.11694(11) -0.09281(17) 0.0607(8) Uani 1 1 d . . . C12 C 0.0395(4) 0.09402(10) -0.02605(17) 0.0577(7) Uani 1 1 d . . . C13 C 0.1587(3) 0.09360(9) 0.04461(15) 0.0488(6) Uani 1 1 d . . . C14 C 0.1063(6) 0.07121(17) 0.1192(2) 0.0735(9) Uani 1 1 d . . . C15 C -0.1406(5) 0.0708(2) -0.0284(4) 0.0952(13) Uani 1 1 d . . . N21 N 0.8082(3) 0.37566(9) 0.17328(16) 0.0626(7) Uani 1 1 d . . . O21 O 0.9211(2) 0.23536(6) 0.28126(9) 0.0405(4) Uani 1 1 d . . . O22 O 0.7245(2) 0.29446(6) 0.25174(11) 0.0549(5) Uani 1 1 d . . . C21 C 0.8750(3) 0.27823(9) 0.25132(13) 0.0381(5) Uani 1 1 d . . . C22 C 1.0108(3) 0.30778(8) 0.21660(13) 0.0372(5) Uani 1 1 d . . . C23 C 1.1805(3) 0.28876(10) 0.22294(14) 0.0426(5) Uani 1 1 d . . . C24 C 1.3163(3) 0.31535(11) 0.19834(16) 0.0526(7) Uani 1 1 d . . . C25 C 1.2819(3) 0.36289(11) 0.16676(16) 0.0550(7) Uani 1 1 d . . . C26 C 1.1165(3) 0.38267(11) 0.15831(16) 0.0514(6) Uani 1 1 d . . . C27 C 0.9757(3) 0.35580(9) 0.18220(14) 0.0451(6) Uani 1 1 d . . . C28 C 0.7650(3) 0.42708(10) 0.14872(16) 0.0508(6) Uani 1 1 d . . . C29 C 0.7167(4) 0.45977(14) 0.2054(2) 0.0707(9) Uani 1 1 d . . . C30 C 0.6755(5) 0.50914(16) 0.1799(3) 0.0948(13) Uani 1 1 d . . . C31 C 0.6902(5) 0.52342(15) 0.1037(3) 0.0821(10) Uani 1 1 d . . . C32 C 0.7356(3) 0.49048(11) 0.0470(2) 0.0624(8) Uani 1 1 d . . . C33 C 0.7721(3) 0.44013(10) 0.07061(16) 0.0512(6) Uani 1 1 d . . . C34 C 0.8072(4) 0.40316(12) 0.01000(17) 0.0673(8) Uani 1 1 d . . . H34A H 0.7171 0.4059 -0.0367 0.087 Uiso 1 1 calc R . . H34B H 0.8049 0.3694 0.0324 0.087 Uiso 1 1 calc R . . H34C H 0.9228 0.4096 -0.0061 0.087 Uiso 1 1 calc R . . C35 C 0.7488(5) 0.50779(18) -0.0353(2) 0.1019(14) Uani 1 1 d . . . H35A H 0.6722 0.4873 -0.0735 0.132 Uiso 1 1 calc R . . H35B H 0.8704 0.5045 -0.0460 0.132 Uiso 1 1 calc R . . H35C H 0.7126 0.5429 -0.0408 0.132 Uiso 1 1 calc R . . N41 N 0.7781(2) 0.24191(7) 0.43017(11) 0.0386(4) Uani 1 1 d . . . N42 N 0.4955(2) 0.19481(7) 0.37056(13) 0.0469(5) Uani 1 1 d . . . C41 C 0.9284(3) 0.26611(9) 0.45476(15) 0.0461(6) Uani 1 1 d . . . C42 C 0.9629(5) 0.28688(10) 0.52996(16) 0.0582(7) Uani 1 1 d . . . C43 C 0.8430(5) 0.28256(11) 0.58146(17) 0.0643(8) Uani 1 1 d . . . C44 C 0.6886(5) 0.25779(11) 0.55763(17) 0.0628(8) Uani 1 1 d . . . C45 C 0.6569(3) 0.23711(9) 0.48054(15) 0.0459(6) Uani 1 1 d . . . C46 C 0.4983(3) 0.20989(9) 0.44701(17) 0.0511(7) Uani 1 1 d . . . C47 C 0.3600(5) 0.19939(13) 0.4886(3) 0.0788(11) Uani 1 1 d . . . C48 C 0.2186(5) 0.17373(15) 0.4525(4) 0.0953(14) Uani 1 1 d . . . C49 C 0.2123(4) 0.15921(14) 0.3750(4) 0.0876(14) Uani 1 1 d . . . C50 C 0.3551(4) 0.16988(11) 0.3353(2) 0.0630(8) Uani 1 1 d . . . H3 H 0.850(3) 0.0386(10) 0.2786(16) 0.054(8) Uiso 1 1 d . . . H4 H 0.802(4) -0.0376(11) 0.2122(18) 0.068(9) Uiso 1 1 d . . . H5 H 0.592(4) -0.0438(12) 0.1036(18) 0.073(9) Uiso 1 1 d . . . H6 H 0.434(4) 0.0263(10) 0.0600(17) 0.058(8) Uiso 1 1 d . . . H9 H 0.471(3) 0.1520(9) -0.0247(15) 0.048(7) Uiso 1 1 d . . . H10 H 0.273(4) 0.1538(12) -0.1318(19) 0.073(10) Uiso 1 1 d . . . H11 H 0.005(4) 0.1168(10) -0.1410(17) 0.065(8) Uiso 1 1 d . . . H14A H 0.003(6) 0.0821(15) 0.131(2) 0.113(15) Uiso 1 1 d . . . H14B H 0.122(6) 0.0365(18) 0.120(3) 0.127(17) Uiso 1 1 d . . . H14C H 0.181(5) 0.0805(14) 0.164(2) 0.103(14) Uiso 1 1 d . . . H15A H -0.206(7) 0.074(2) -0.073(3) 0.15(2) Uiso 1 1 d . . . H15B H -0.132(6) 0.0358(19) -0.012(3) 0.126(17) Uiso 1 1 d . . . H15C H -0.207(7) 0.089(2) 0.007(3) 0.15(2) Uiso 1 1 d . . . H1N H 0.491(3) 0.1421(10) 0.1318(16) 0.051(8) Uiso 1 1 d . . . H23 H 1.200(3) 0.2574(10) 0.2449(14) 0.043(7) Uiso 1 1 d . . . H24 H 1.429(4) 0.3044(9) 0.2043(15) 0.050(7) Uiso 1 1 d . . . H25 H 1.376(4) 0.3825(11) 0.1521(17) 0.068(8) Uiso 1 1 d . . . H26 H 1.096(3) 0.4132(10) 0.1380(15) 0.049(7) Uiso 1 1 d . . . H29 H 0.724(4) 0.4467(11) 0.2556(18) 0.062(9) Uiso 1 1 d . . . H30 H 0.639(5) 0.5362(16) 0.215(3) 0.125(15) Uiso 1 1 d . . . H31 H 0.660(5) 0.5582(15) 0.094(2) 0.102(13) Uiso 1 1 d . . . H2N H 0.736(4) 0.3601(12) 0.1975(18) 0.072(10) Uiso 1 1 d . . . H41 H 1.012(3) 0.2697(10) 0.4150(16) 0.055(7) Uiso 1 1 d . . . H42 H 1.067(4) 0.3021(12) 0.5442(18) 0.070(9) Uiso 1 1 d . . . H43 H 0.861(4) 0.2961(11) 0.637(2) 0.079(10) Uiso 1 1 d . . . H44 H 0.606(4) 0.2534(10) 0.5872(17) 0.059(8) Uiso 1 1 d . . . H47 H 0.363(5) 0.2076(13) 0.540(2) 0.090(13) Uiso 1 1 d . . . H48 H 0.119(5) 0.1631(14) 0.484(2) 0.110(12) Uiso 1 1 d . . . H49 H 0.137(4) 0.1442(11) 0.3427(18) 0.062(9) Uiso 1 1 d . . . H50 H 0.358(3) 0.1609(9) 0.2878(15) 0.037(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0415(2) 0.0365(2) 0.0329(2) 0.00076(13) 0.00124(14) -0.00737(13) N1 0.0634(13) 0.0352(12) 0.0433(12) -0.0051(9) -0.0178(10) 0.0017(10) O1 0.0499(9) 0.0472(9) 0.0343(9) 0.0018(7) -0.0063(7) -0.0083(7) O2 0.0646(10) 0.0371(9) 0.0370(9) 0.0010(7) -0.0081(7) -0.0075(7) C1 0.0423(12) 0.0410(13) 0.0316(12) 0.0013(10) 0.0039(9) -0.0093(9) C2 0.0428(12) 0.0388(12) 0.0309(12) 0.0016(9) 0.0023(9) -0.0045(9) C3 0.0508(14) 0.0501(15) 0.0377(14) 0.0019(11) -0.0027(11) 0.0017(11) C4 0.0717(18) 0.0443(16) 0.0522(17) 0.0005(13) -0.0050(13) 0.0135(13) C5 0.0796(19) 0.0399(15) 0.0508(16) -0.0085(13) -0.0020(14) 0.0048(13) C6 0.0631(16) 0.0436(14) 0.0384(14) -0.0062(11) -0.0074(12) 0.0011(11) C7 0.0471(12) 0.0374(12) 0.0343(12) 0.0009(10) 0.0006(10) -0.0006(10) C8 0.0574(14) 0.0362(13) 0.0339(12) -0.0045(10) -0.0074(10) 0.0057(10) C9 0.0614(17) 0.0421(15) 0.0506(16) 0.0019(12) 0.0047(13) 0.0037(12) C10 0.094(2) 0.0558(17) 0.0357(15) 0.0098(13) 0.0071(15) 0.0256(16) C11 0.0708(19) 0.0617(18) 0.0427(16) -0.0117(13) -0.0169(14) 0.0175(15) C12 0.0597(16) 0.0522(16) 0.0558(17) -0.0095(13) -0.0124(13) 0.0059(12) C13 0.0559(14) 0.0457(14) 0.0418(14) -0.0027(11) -0.0041(11) 0.0021(11) C14 0.073(2) 0.084(3) 0.063(2) 0.0121(19) 0.0097(18) -0.0054(19) C15 0.065(2) 0.099(3) 0.112(4) -0.008(3) -0.021(2) -0.012(2) N21 0.0411(12) 0.0602(15) 0.0885(19) 0.0362(13) 0.0159(12) 0.0042(10) O21 0.0501(9) 0.0378(9) 0.0346(8) 0.0030(7) 0.0090(7) -0.0027(7) O22 0.0353(9) 0.0607(11) 0.0691(12) 0.0247(9) 0.0082(8) -0.0024(7) C21 0.0403(12) 0.0444(13) 0.0283(11) 0.0007(10) -0.0005(9) -0.0084(10) C22 0.0359(11) 0.0434(13) 0.0316(12) 0.0026(10) 0.0017(9) -0.0050(9) C23 0.0438(13) 0.0488(15) 0.0352(13) 0.0027(11) 0.0055(10) 0.0028(10) C24 0.0350(13) 0.0749(19) 0.0484(15) 0.0047(13) 0.0076(11) 0.0019(12) C25 0.0408(14) 0.0715(19) 0.0538(16) 0.0111(14) 0.0101(12) -0.0120(12) C26 0.0460(14) 0.0533(17) 0.0554(16) 0.0145(13) 0.0084(12) -0.0092(11) C27 0.0369(12) 0.0529(15) 0.0451(14) 0.0091(11) 0.0043(10) -0.0052(10) C28 0.0416(13) 0.0628(17) 0.0480(15) 0.0066(13) 0.0051(11) -0.0050(11) C29 0.0662(19) 0.084(2) 0.062(2) -0.0120(18) 0.0086(16) 0.0196(16) C30 0.084(2) 0.089(3) 0.104(3) -0.049(3) -0.014(2) 0.025(2) C31 0.067(2) 0.067(2) 0.105(3) 0.010(2) -0.015(2) -0.0012(17) C32 0.0432(14) 0.0484(16) 0.094(2) 0.0138(16) 0.0043(14) -0.0068(11) C33 0.0433(13) 0.0578(16) 0.0525(16) -0.0013(13) 0.0062(11) -0.0034(11) C34 0.0722(19) 0.080(2) 0.0493(17) -0.0092(15) 0.0060(14) 0.0005(15) C35 0.069(2) 0.130(3) 0.106(3) 0.064(3) 0.008(2) -0.002(2) N41 0.0498(11) 0.0343(10) 0.0329(10) 0.0013(8) 0.0093(8) -0.0018(8) N42 0.0370(10) 0.0402(11) 0.0620(14) 0.0154(10) 0.0017(9) -0.0015(8) C41 0.0576(15) 0.0420(14) 0.0377(13) -0.0012(11) 0.0026(11) -0.0101(11) C42 0.090(2) 0.0439(16) 0.0371(15) -0.0033(11) -0.0050(14) -0.0071(14) C43 0.110(3) 0.0473(16) 0.0347(15) 0.0004(12) 0.0057(16) 0.0068(16) C44 0.097(2) 0.0565(18) 0.0411(16) 0.0117(13) 0.0324(16) 0.0246(16) C45 0.0579(14) 0.0376(13) 0.0452(14) 0.0113(11) 0.0181(11) 0.0099(10) C46 0.0499(14) 0.0418(14) 0.0650(18) 0.0185(12) 0.0202(13) 0.0105(10) C47 0.070(2) 0.068(2) 0.109(3) 0.023(2) 0.051(2) 0.0064(16) C48 0.063(2) 0.077(3) 0.155(4) 0.040(3) 0.050(3) 0.0083(18) C49 0.0353(16) 0.056(2) 0.166(5) 0.042(3) -0.005(2) -0.0075(13) C50 0.0438(15) 0.0531(17) 0.088(3) 0.0217(17) -0.0046(15) -0.0067(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 Cu O21 1.9440(15) . ? Cu O2 1.9796(16) . ? Cu N41 1.9971(18) . ? Cu N42 2.0063(19) . ? Cu O1 2.4133(16) . ? Cu C1 2.534(2) . ? N1 C7 1.380(3) . ? N1 C8 1.424(3) . ? N1 H1N 0.81(3) . ? O1 C1 1.245(3) . ? O2 C1 1.296(3) . ? C1 C2 1.488(3) . ? C2 C3 1.396(3) . ? C2 C7 1.411(3) . ? C3 C4 1.373(4) . ? C3 H3 0.90(3) . ? C4 C5 1.382(4) . ? C4 H4 0.89(3) . ? C5 C6 1.371(4) . ? C5 H5 0.95(3) . ? C6 C7 1.403(3) . ? C6 H6 0.92(3) . ? C8 C9 1.383(4) . ? C8 C13 1.391(4) . ? C9 C10 1.396(4) . ? C9 H9 0.89(3) . ? C10 C11 1.358(5) . ? C10 H10 0.83(3) . ? C11 C12 1.368(4) . ? C11 H11 0.95(3) . ? C12 C13 1.405(3) . ? C12 C15 1.513(5) . ? C13 C14 1.499(4) . ? C14 H14A 0.90(4) . ? C14 H14B 0.94(5) . ? C14 H14C 0.92(4) . ? C15 H15A 0.85(5) . ? C15 H15B 0.97(5) . ? C15 H15C 0.97(5) . ? N21 C27 1.383(3) . ? N21 C28 1.460(3) . ? N21 H2N 0.84(3) . ? O21 C21 1.282(3) . ? O22 C21 1.238(3) . ? C21 C22 1.491(3) . ? C22 C23 1.392(3) . ? C22 C27 1.419(3) . ? C23 C24 1.373(3) . ? C23 H23 0.92(3) . ? C24 C25 1.389(4) . ? C24 H24 0.91(3) . ? C25 C26 1.367(4) . ? C25 H25 0.95(3) . ? C26 C27 1.404(3) . ? C26 H26 0.89(3) . ? C28 C33 1.374(4) . ? C28 C29 1.383(4) . ? C29 C30 1.410(6) . ? C29 H29 0.91(3) . ? C30 C31 1.363(6) . ? C30 H30 1.00(4) . ? C31 C32 1.380(5) . ? C31 H31 0.96(4) . ? C32 C33 1.420(4) . ? C32 C35 1.483(5) . ? C33 C34 1.474(4) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? N41 C41 1.341(3) . ? N41 C45 1.351(3) . ? N42 C50 1.339(3) . ? N42 C46 1.351(3) . ? C41 C42 1.380(4) . ? C41 H41 1.00(3) . ? C42 C43 1.357(5) . ? C42 H42 0.90(3) . ? C43 C44 1.372(5) . ? C43 H43 1.00(3) . ? C44 C45 1.406(4) . ? C44 H44 0.87(3) . ? C45 C46 1.467(4) . ? C46 C47 1.381(4) . ? C47 C48 1.359(6) . ? C47 H47 0.89(4) . ? C48 C49 1.361(6) . ? C48 H48 1.02(4) . ? C49 C50 1.393(5) . ? C49 H49 0.84(3) . ? C50 H50 0.84(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O21 Cu O2 93.83(7) . . ? O21 Cu N41 94.15(7) . . ? O2 Cu N41 168.69(7) . . ? O21 Cu N42 171.03(7) . . ? O2 Cu N42 92.26(8) . . ? N41 Cu N42 80.80(8) . . ? O21 Cu O1 94.19(6) . . ? O2 Cu O1 59.22(6) . . ? N41 Cu O1 112.14(6) . . ? N42 Cu O1 94.58(7) . . ? O21 Cu C1 96.38(7) . . ? O2 Cu C1 30.31(7) . . ? N41 Cu C1 140.29(7) . . ? N42 Cu C1 92.20(8) . . ? O1 Cu C1 29.00(6) . . ? C7 N1 C8 123.9(2) . . ? C7 N1 H1N 112.4(19) . . ? C8 N1 H1N 120.0(19) . . ? C1 O1 Cu 80.91(13) . . ? C1 O2 Cu 99.26(13) . . ? O1 C1 O2 120.2(2) . . ? O1 C1 C2 120.8(2) . . ? O2 C1 C2 119.00(19) . . ? O1 C1 Cu 70.09(12) . . ? O2 C1 Cu 50.43(10) . . ? C2 C1 Cu 167.66(16) . . ? C3 C2 C7 118.9(2) . . ? C3 C2 C1 117.5(2) . . ? C7 C2 C1 123.5(2) . . ? C4 C3 C2 122.1(2) . . ? C4 C3 H3 121.7(17) . . ? C2 C3 H3 116.1(17) . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 123(2) . . ? C5 C4 H4 118(2) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 118.6(18) . . ? C4 C5 H5 120.2(18) . . ? C5 C6 C7 121.0(2) . . ? C5 C6 H6 120.6(17) . . ? C7 C6 H6 118.4(17) . . ? N1 C7 C6 120.3(2) . . ? N1 C7 C2 121.5(2) . . ? C6 C7 C2 118.2(2) . . ? C9 C8 C13 120.5(2) . . ? C9 C8 N1 119.2(2) . . ? C13 C8 N1 120.3(2) . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.8(17) . . ? C10 C9 H9 119.7(17) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 124(2) . . ? C9 C10 H10 116(2) . . ? C10 C11 C12 121.5(3) . . ? C10 C11 H11 118.6(17) . . ? C12 C11 H11 119.9(17) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 C15 119.6(3) . . ? C13 C12 C15 120.6(3) . . ? C8 C13 C12 118.8(2) . . ? C8 C13 C14 121.2(3) . . ? C12 C13 C14 120.0(3) . . ? C13 C14 H14A 114(3) . . ? C13 C14 H14B 111(3) . . ? H14A C14 H14B 116(4) . . ? C13 C14 H14C 112(2) . . ? H14A C14 H14C 102(3) . . ? H14B C14 H14C 101(4) . . ? C12 C15 H15A 114(4) . . ? C12 C15 H15B 111(3) . . ? H15A C15 H15B 111(4) . . ? C12 C15 H15C 110(3) . . ? H15A C15 H15C 102(4) . . ? H15B C15 H15C 109(4) . . ? C27 N21 C28 124.4(2) . . ? C27 N21 H2N 115(2) . . ? C28 N21 H2N 118(2) . . ? C21 O21 Cu 105.18(13) . . ? O22 C21 O21 121.3(2) . . ? O22 C21 C22 121.5(2) . . ? O21 C21 C22 117.2(2) . . ? C23 C22 C27 119.1(2) . . ? C23 C22 C21 118.4(2) . . ? C27 C22 C21 122.4(2) . . ? C24 C23 C22 122.2(2) . . ? C24 C23 H23 120.3(15) . . ? C22 C23 H23 117.5(15) . . ? C23 C24 C25 118.4(2) . . ? C23 C24 H24 123.7(16) . . ? C25 C24 H24 117.8(16) . . ? C26 C25 C24 121.3(2) . . ? C26 C25 H25 119.4(17) . . ? C24 C25 H25 119.3(17) . . ? C25 C26 C27 121.1(3) . . ? C25 C26 H26 120.6(16) . . ? C27 C26 H26 118.3(16) . . ? N21 C27 C26 121.1(2) . . ? N21 C27 C22 120.9(2) . . ? C26 C27 C22 117.9(2) . . ? C33 C28 C29 123.7(3) . . ? C33 C28 N21 118.3(2) . . ? C29 C28 N21 117.9(3) . . ? C28 C29 C30 116.6(4) . . ? C28 C29 H29 114.6(19) . . ? C30 C29 H29 128.6(19) . . ? C31 C30 C29 120.5(4) . . ? C31 C30 H30 115(2) . . ? C29 C30 H30 125(2) . . ? C30 C31 C32 122.6(4) . . ? C30 C31 H31 112(2) . . ? C32 C31 H31 125(2) . . ? C31 C32 C33 117.9(3) . . ? C31 C32 C35 120.6(3) . . ? C33 C32 C35 121.5(3) . . ? C28 C33 C32 118.6(3) . . ? C28 C33 C34 122.2(3) . . ? C32 C33 C34 119.1(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C41 N41 C45 119.3(2) . . ? C41 N41 Cu 125.42(16) . . ? C45 N41 Cu 115.23(16) . . ? C50 N42 C46 118.8(3) . . ? C50 N42 Cu 126.6(2) . . ? C46 N42 Cu 114.52(16) . . ? N41 C41 C42 122.0(3) . . ? N41 C41 H41 116.4(15) . . ? C42 C41 H41 121.5(15) . . ? C43 C42 C41 119.6(3) . . ? C43 C42 H42 122(2) . . ? C41 C42 H42 119(2) . . ? C42 C43 C44 119.3(3) . . ? C42 C43 H43 123.5(19) . . ? C44 C43 H43 117.2(18) . . ? C43 C44 C45 119.8(3) . . ? C43 C44 H44 124.6(19) . . ? C45 C44 H44 115.7(19) . . ? N41 C45 C44 119.9(3) . . ? N41 C45 C46 114.3(2) . . ? C44 C45 C46 125.7(2) . . ? N42 C46 C47 120.9(3) . . ? N42 C46 C45 115.0(2) . . ? C47 C46 C45 124.2(3) . . ? C48 C47 C46 119.9(4) . . ? C48 C47 H47 118(3) . . ? C46 C47 H47 122(3) . . ? C47 C48 C49 119.9(4) . . ? C47 C48 H48 121(2) . . ? C49 C48 H48 119(2) . . ? C48 C49 C50 118.6(4) . . ? C48 C49 H49 134(2) . . ? C50 C49 H49 108(2) . . ? N42 C50 C49 121.9(4) . . ? N42 C50 H50 116.4(18) . . ? C49 C50 H50 121.7(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.612 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.045 # Attachment 'pssf14.cif' data_pssf14 _database_code_depnum_ccdc_archive 'CCDC 797034' #TrackingRef 'pssf14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H41 Cu N5 O5' _chemical_formula_weight 747.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1512(2) _cell_length_b 14.0929(2) _cell_length_c 23.7121(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.7950(10) _cell_angle_gamma 90.00 _cell_volume 3647.74(10) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 40184 _cell_measurement_theta_min 6.52 _cell_measurement_theta_max 71.89 _exptl_crystal_description parallelepiped _exptl_crystal_colour green _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1564 _exptl_absorpt_coefficient_mu 1.268 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrystalClear, Rigaku MSC, 2005' _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS SPIDER IPDS' _diffrn_measurement_method '\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41459 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 6.53 _diffrn_reflns_theta_max 64.99 _reflns_number_total 6180 _reflns_number_gt 5774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, Rigaku MSC, 2005' _computing_cell_refinement 'CrystalClear, Rigaku MSC, 2005' _computing_data_reduction 'CrystalClear, Rigaku MSC, 2005' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+2.0067P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6180 _refine_ls_number_parameters 633 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0910 _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 Cu Cu 0.24450(2) 0.002420(16) 0.407080(10) 0.02224(10) Uani 1 1 d . . . N1 N 0.25814(12) -0.02996(10) 0.48975(6) 0.0231(3) Uani 1 1 d . . . N2 N 0.45130(13) -0.10383(10) 0.50024(6) 0.0229(3) Uani 1 1 d . . . N3 N 0.37867(13) -0.08819(10) 0.39949(6) 0.0255(3) Uani 1 1 d . . . C1 C 0.16585(17) -0.00178(13) 0.51575(9) 0.0304(4) Uani 1 1 d . . . C2 C 0.17042(19) -0.00782(14) 0.57335(9) 0.0344(4) Uani 1 1 d . . . C3 C 0.27757(18) -0.04280(14) 0.60836(9) 0.0333(4) Uani 1 1 d . . . C4 C 0.37074(17) -0.07338(13) 0.58377(8) 0.0281(4) Uani 1 1 d . . . C5 C 0.35747(14) -0.06851(11) 0.52356(7) 0.0219(3) Uani 1 1 d . . . C6 C 0.45989(14) -0.12307(11) 0.44427(7) 0.0228(3) Uani 1 1 d . . . C7 C 0.55807(17) -0.18061(13) 0.43665(9) 0.0307(4) Uani 1 1 d . . . C8 C 0.57178(19) -0.20330(15) 0.38257(9) 0.0393(5) Uani 1 1 d . . . C9 C 0.4882(2) -0.16796(17) 0.33593(10) 0.0465(5) Uani 1 1 d . . . C10 C 0.3951(2) -0.11166(15) 0.34612(9) 0.0383(5) Uani 1 1 d . . . N11 N 0.01665(14) 0.24596(11) 0.46062(7) 0.0304(4) Uani 1 1 d . . . O11 O 0.15660(10) 0.12256(8) 0.41878(5) 0.0268(3) Uani 1 1 d . . . O12 O 0.34815(10) 0.16060(9) 0.41802(5) 0.0301(3) Uani 1 1 d . . . C11 C 0.24349(15) 0.18343(12) 0.42545(7) 0.0248(4) Uani 1 1 d . . . C12 C 0.22109(15) 0.28120(12) 0.44452(7) 0.0245(4) Uani 1 1 d . . . C13 C 0.31483(16) 0.34831(13) 0.44721(8) 0.0286(4) Uani 1 1 d . . . C14 C 0.30557(17) 0.43861(13) 0.46824(8) 0.0324(4) Uani 1 1 d . . . C15 C 0.20026(18) 0.46338(13) 0.48742(9) 0.0336(4) Uani 1 1 d . . . C16 C 0.10576(17) 0.39949(13) 0.48494(9) 0.0312(4) Uani 1 1 d . . . C17 C 0.11259(15) 0.30741(12) 0.46302(7) 0.0249(4) Uani 1 1 d . . . C18 C -0.08849(16) 0.26574(12) 0.48388(8) 0.0294(4) Uani 1 1 d . . . C19 C -0.19932(17) 0.28180(13) 0.44623(10) 0.0344(4) Uani 1 1 d . . . C20 C -0.30347(18) 0.29973(14) 0.46808(11) 0.0409(5) Uani 1 1 d . . . C21 C -0.29561(19) 0.30243(13) 0.52671(11) 0.0413(5) Uani 1 1 d . . . C22 C -0.18566(19) 0.28626(13) 0.56520(10) 0.0386(5) Uani 1 1 d . . . C23 C -0.07911(17) 0.26736(12) 0.54365(9) 0.0322(4) Uani 1 1 d . . . C24 C -0.1794(3) 0.28825(18) 0.62909(12) 0.0532(6) Uani 1 1 d . . . C25 C 0.0407(2) 0.24870(17) 0.58424(10) 0.0433(5) Uani 1 1 d . . . N31 N -0.15516(15) -0.07983(13) 0.25769(8) 0.0401(4) Uani 1 1 d . . . O31 O 0.19898(10) 0.02495(9) 0.32428(5) 0.0282(3) Uani 1 1 d . . . O32 O 0.03979(11) -0.05254(9) 0.34317(5) 0.0324(3) Uani 1 1 d . . . C31 C 0.09098(16) -0.01074(12) 0.30804(8) 0.0248(4) Uani 1 1 d . . . C32 C 0.03355(16) -0.00174(11) 0.24587(8) 0.0259(4) Uani 1 1 d . . . C33 C 0.10079(18) 0.03915(14) 0.20871(8) 0.0336(4) Uani 1 1 d . . . C34 C 0.0555(2) 0.04656(18) 0.15053(9) 0.0462(5) Uani 1 1 d . . . C35 C -0.0611(2) 0.01265(17) 0.12804(10) 0.0478(6) Uani 1 1 d . . . C36 C -0.13011(19) -0.02871(17) 0.16323(9) 0.0417(5) Uani 1 1 d . . . C37 C -0.08526(17) -0.03760(14) 0.22279(8) 0.0318(4) Uani 1 1 d . . . C38 C -0.26870(17) -0.12838(15) 0.23532(8) 0.0350(4) Uani 1 1 d . . . C39 C -0.2696(2) -0.22625(15) 0.23482(10) 0.0418(5) Uani 1 1 d . . . C40 C -0.3789(2) -0.27428(16) 0.21330(10) 0.0444(5) Uani 1 1 d . . . C41 C -0.48358(19) -0.22296(16) 0.19314(9) 0.0400(5) Uani 1 1 d . . . C42 C -0.48584(18) -0.12487(15) 0.19416(8) 0.0354(4) Uani 1 1 d . . . C43 C -0.37449(18) -0.07546(14) 0.21575(8) 0.0345(4) Uani 1 1 d . . . C44 C -0.3754(2) 0.02970(18) 0.21759(11) 0.0457(5) Uani 1 1 d . . . C45 C -0.6020(2) -0.0704(2) 0.17584(12) 0.0508(6) Uani 1 1 d . . . OM O 0.39959(17) 0.13549(14) 0.29030(8) 0.0587(5) Uani 1 1 d . . . CM C 0.3976(5) 0.2349(3) 0.29031(17) 0.0826(10) Uani 1 1 d . . . H2N H 0.5049(19) -0.1246(15) 0.5234(9) 0.029(5) Uiso 1 1 d . . . H11N H 0.0197(19) 0.1999(16) 0.4430(9) 0.031(6) Uiso 1 1 d . . . H31N H -0.116(2) -0.0913(17) 0.2935(11) 0.050(7) Uiso 1 1 d . . . H1 H 0.098(2) 0.0243(15) 0.4890(9) 0.036(5) Uiso 1 1 d . . . H2 H 0.106(2) 0.0110(14) 0.5881(10) 0.037(6) Uiso 1 1 d . . . H3 H 0.2842(19) -0.0449(16) 0.6484(10) 0.039(6) Uiso 1 1 d . . . H4 H 0.4413(19) -0.0965(14) 0.6054(9) 0.032(5) Uiso 1 1 d . . . H7 H 0.608(2) -0.2036(16) 0.4679(10) 0.039(6) Uiso 1 1 d . . . H8 H 0.637(2) -0.2425(17) 0.3782(10) 0.050(6) Uiso 1 1 d . . . H9 H 0.491(2) -0.1816(19) 0.2960(12) 0.064(8) Uiso 1 1 d . . . H10 H 0.338(2) -0.0876(16) 0.3149(10) 0.045(6) Uiso 1 1 d . . . H13 H 0.3842(18) 0.3294(14) 0.4327(8) 0.027(5) Uiso 1 1 d . . . H14 H 0.368(2) 0.4831(15) 0.4696(9) 0.036(6) Uiso 1 1 d . . . H15 H 0.1929(19) 0.5219(16) 0.5012(9) 0.035(6) Uiso 1 1 d . . . H16 H 0.0346(19) 0.4164(14) 0.4987(8) 0.032(5) Uiso 1 1 d . . . H19 H -0.2021(19) 0.2811(15) 0.4084(10) 0.032(6) Uiso 1 1 d . . . H20 H -0.376(2) 0.3096(15) 0.4421(10) 0.040(6) Uiso 1 1 d . . . H21 H -0.366(2) 0.3159(16) 0.5416(9) 0.042(6) Uiso 1 1 d . . . H24A H -0.258(3) 0.2956(19) 0.6361(12) 0.063(8) Uiso 1 1 d . . . H24B H -0.147(2) 0.227(2) 0.6471(11) 0.056(7) Uiso 1 1 d . . . H24C H -0.131(3) 0.340(2) 0.6494(12) 0.071(9) Uiso 1 1 d . . . H25A H 0.100(2) 0.2205(18) 0.5637(11) 0.057(7) Uiso 1 1 d . . . H25B H 0.031(2) 0.204(2) 0.6132(12) 0.062(8) Uiso 1 1 d . . . H25C H 0.076(3) 0.309(2) 0.6048(13) 0.080(9) Uiso 1 1 d . . . H33 H 0.178(2) 0.0599(15) 0.2247(9) 0.037(6) Uiso 1 1 d . . . H34 H 0.102(2) 0.0736(18) 0.1250(11) 0.054(7) Uiso 1 1 d . . . H35 H -0.091(3) 0.0143(19) 0.0887(13) 0.067(8) Uiso 1 1 d . . . H36 H -0.212(2) -0.0528(16) 0.1467(9) 0.040(6) Uiso 1 1 d . . . H39 H -0.1893(19) -0.2518(14) 0.2491(8) 0.028(5) Uiso 1 1 d . . . H40 H -0.384(2) -0.3425(19) 0.2116(10) 0.054(7) Uiso 1 1 d . . . H41 H -0.559(2) -0.2591(18) 0.1783(11) 0.057(7) Uiso 1 1 d . . . H44A H -0.294(3) 0.049(2) 0.2319(12) 0.069(8) Uiso 1 1 d . . . H44B H -0.432(3) 0.052(2) 0.2390(12) 0.068(8) Uiso 1 1 d . . . H44C H -0.401(2) 0.0550(19) 0.1804(12) 0.060(8) Uiso 1 1 d . . . H45A H -0.614(2) -0.024(2) 0.2069(13) 0.062(8) Uiso 1 1 d . . . H45B H -0.671(3) -0.116(2) 0.1666(12) 0.066(8) Uiso 1 1 d . . . H45C H -0.597(3) -0.030(3) 0.1397(16) 0.099(11) Uiso 1 1 d . . . H1OM H 0.343(3) 0.114(2) 0.3048(15) 0.092(12) Uiso 1 1 d . . . H1M H 0.313(4) 0.261(3) 0.2732(17) 0.117(15) Uiso 1 1 d . . . H2M H 0.448(3) 0.256(2) 0.2678(16) 0.091(11) Uiso 1 1 d . . . H3M H 0.409(3) 0.261(3) 0.3287(18) 0.108(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01848(15) 0.02593(15) 0.02177(16) -0.00064(9) 0.00283(10) 0.00249(9) N1 0.0186(7) 0.0264(7) 0.0248(8) -0.0001(6) 0.0055(6) 0.0005(6) N2 0.0181(7) 0.0261(7) 0.0233(8) 0.0010(6) 0.0014(6) 0.0026(6) N3 0.0249(7) 0.0268(7) 0.0251(8) -0.0002(6) 0.0062(6) 0.0032(6) C1 0.0240(9) 0.0363(10) 0.0330(11) 0.0023(8) 0.0104(8) 0.0039(7) C2 0.0317(10) 0.0396(11) 0.0359(12) -0.0021(8) 0.0164(9) 0.0019(8) C3 0.0406(11) 0.0360(10) 0.0250(10) -0.0010(8) 0.0108(8) -0.0021(8) C4 0.0286(9) 0.0283(9) 0.0262(10) 0.0004(7) 0.0026(7) -0.0010(7) C5 0.0203(8) 0.0197(8) 0.0257(9) -0.0019(6) 0.0044(7) -0.0039(6) C6 0.0206(8) 0.0200(8) 0.0284(9) 0.0002(7) 0.0066(7) -0.0020(6) C7 0.0271(9) 0.0327(10) 0.0327(11) 0.0033(8) 0.0069(8) 0.0063(8) C8 0.0381(11) 0.0410(11) 0.0430(12) 0.0008(9) 0.0183(9) 0.0139(9) C9 0.0563(13) 0.0569(14) 0.0301(11) 0.0005(10) 0.0176(10) 0.0203(11) C10 0.0438(11) 0.0474(12) 0.0243(10) 0.0018(8) 0.0079(9) 0.0163(9) N11 0.0282(8) 0.0223(8) 0.0440(10) -0.0067(7) 0.0150(7) -0.0012(6) O11 0.0231(6) 0.0256(6) 0.0311(7) -0.0023(5) 0.0042(5) 0.0028(5) O12 0.0204(6) 0.0374(7) 0.0313(7) -0.0041(5) 0.0023(5) 0.0064(5) C11 0.0228(8) 0.0315(9) 0.0188(8) 0.0015(7) 0.0007(6) 0.0042(7) C12 0.0226(8) 0.0275(9) 0.0222(9) 0.0026(7) 0.0016(7) 0.0015(7) C13 0.0219(9) 0.0360(10) 0.0274(10) 0.0025(8) 0.0040(7) 0.0004(7) C14 0.0303(9) 0.0317(10) 0.0344(11) 0.0015(8) 0.0045(8) -0.0083(8) C15 0.0375(10) 0.0250(10) 0.0388(11) -0.0035(8) 0.0088(8) -0.0037(8) C16 0.0306(9) 0.0263(9) 0.0393(11) -0.0011(8) 0.0131(8) 0.0005(7) C17 0.0242(8) 0.0245(8) 0.0262(9) 0.0022(7) 0.0054(7) -0.0001(7) C18 0.0278(9) 0.0186(8) 0.0452(11) -0.0037(7) 0.0154(8) -0.0033(7) C19 0.0303(10) 0.0277(9) 0.0459(13) -0.0072(8) 0.0098(9) -0.0053(7) C20 0.0250(10) 0.0284(10) 0.0700(16) -0.0082(10) 0.0113(10) -0.0034(8) C21 0.0355(11) 0.0224(9) 0.0747(17) -0.0078(9) 0.0317(11) -0.0055(8) C22 0.0482(12) 0.0202(9) 0.0553(13) -0.0020(8) 0.0292(10) -0.0031(8) C23 0.0354(10) 0.0196(8) 0.0452(12) -0.0007(8) 0.0168(9) -0.0015(7) C24 0.0738(17) 0.0411(13) 0.0562(15) -0.0005(11) 0.0403(14) 0.0020(12) C25 0.0493(13) 0.0390(12) 0.0424(13) 0.0055(10) 0.0115(10) 0.0052(10) N31 0.0313(9) 0.0583(11) 0.0278(9) 0.0065(8) -0.0006(7) -0.0135(8) O31 0.0204(6) 0.0379(7) 0.0246(7) -0.0004(5) 0.0007(5) 0.0002(5) O32 0.0330(7) 0.0399(7) 0.0234(7) 0.0031(5) 0.0033(5) -0.0049(6) C31 0.0220(9) 0.0259(8) 0.0257(10) -0.0018(7) 0.0031(7) 0.0042(6) C32 0.0244(9) 0.0280(9) 0.0243(10) -0.0014(7) 0.0024(7) 0.0006(6) C33 0.0287(10) 0.0403(11) 0.0308(10) -0.0006(8) 0.0036(8) -0.0092(8) C34 0.0487(12) 0.0622(14) 0.0274(11) 0.0067(10) 0.0073(9) -0.0195(11) C35 0.0515(13) 0.0659(15) 0.0224(11) 0.0057(10) -0.0008(10) -0.0166(11) C36 0.0341(11) 0.0589(13) 0.0283(11) 0.0012(10) -0.0025(9) -0.0122(10) C37 0.0292(9) 0.0379(10) 0.0273(10) -0.0002(8) 0.0038(8) -0.0037(8) C38 0.0311(10) 0.0468(11) 0.0269(10) 0.0043(8) 0.0053(8) -0.0032(8) C39 0.0401(12) 0.0412(11) 0.0435(12) 0.0065(9) 0.0074(9) 0.0011(9) C40 0.0482(12) 0.0379(12) 0.0486(13) 0.0001(10) 0.0132(10) -0.0045(9) C41 0.0373(11) 0.0502(12) 0.0320(11) -0.0072(9) 0.0061(9) -0.0095(9) C42 0.0356(10) 0.0457(11) 0.0243(10) -0.0038(8) 0.0045(8) -0.0015(9) C43 0.0360(10) 0.0405(11) 0.0261(10) -0.0009(8) 0.0045(8) -0.0031(8) C44 0.0430(13) 0.0472(13) 0.0431(14) -0.0036(11) 0.0002(11) 0.0024(10) C45 0.0375(12) 0.0609(15) 0.0491(15) -0.0129(12) -0.0029(10) 0.0026(11) OM 0.0544(10) 0.0664(12) 0.0623(12) -0.0031(9) 0.0281(9) -0.0093(9) CM 0.127(3) 0.069(2) 0.061(2) 0.0011(16) 0.041(2) -0.009(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 Cu O31 1.9508(12) . ? Cu N1 1.9881(14) . ? Cu N3 2.0028(14) . ? Cu O11 2.0039(12) . ? N1 C5 1.342(2) . ? N1 C1 1.362(2) . ? N2 C5 1.373(2) . ? N2 C6 1.377(2) . ? N2 H2N 0.78(2) . ? N3 C6 1.340(2) . ? N3 C10 1.356(2) . ? C1 C2 1.359(3) . ? C1 H1 0.96(2) . ? C2 C3 1.398(3) . ? C2 H2 0.90(2) . ? C3 C4 1.361(3) . ? C3 H3 0.94(2) . ? C4 C5 1.407(2) . ? C4 H4 0.91(2) . ? C6 C7 1.403(2) . ? C7 C8 1.360(3) . ? C7 H7 0.89(2) . ? C8 C9 1.385(3) . ? C8 H8 0.93(2) . ? C9 C10 1.367(3) . ? C9 H9 0.97(3) . ? C10 H10 0.93(2) . ? N11 C17 1.369(2) . ? N11 C18 1.421(2) . ? N11 H11N 0.78(2) . ? O11 C11 1.279(2) . ? O12 C11 1.257(2) . ? C11 C12 1.487(2) . ? C12 C13 1.401(2) . ? C12 C17 1.418(2) . ? C13 C14 1.378(3) . ? C13 H13 0.95(2) . ? C14 C15 1.388(3) . ? C14 H14 0.93(2) . ? C15 C16 1.378(3) . ? C15 H15 0.90(2) . ? C16 C17 1.406(2) . ? C16 H16 0.95(2) . ? C18 C19 1.387(3) . ? C18 C23 1.400(3) . ? C19 C20 1.388(3) . ? C19 H19 0.89(2) . ? C20 C21 1.376(3) . ? C20 H20 0.93(2) . ? C21 C22 1.390(3) . ? C21 H21 0.95(2) . ? C22 C23 1.411(3) . ? C22 C24 1.502(3) . ? C23 C25 1.502(3) . ? C24 H24A 0.94(3) . ? C24 H24B 0.99(3) . ? C24 H24C 0.98(3) . ? C25 H25A 0.98(3) . ? C25 H25B 0.95(3) . ? C25 H25C 1.02(3) . ? N31 C37 1.382(2) . ? N31 C38 1.442(2) . ? N31 H31N 0.89(3) . ? O31 C31 1.289(2) . ? O32 C31 1.250(2) . ? C31 C32 1.488(3) . ? C32 C33 1.393(3) . ? C32 C37 1.419(3) . ? C33 C34 1.373(3) . ? C33 H33 0.91(2) . ? C34 C35 1.385(3) . ? C34 H34 0.95(3) . ? C35 C36 1.375(3) . ? C35 H35 0.93(3) . ? C36 C37 1.404(3) . ? C36 H36 0.98(2) . ? C38 C39 1.379(3) . ? C38 C43 1.393(3) . ? C39 C40 1.396(3) . ? C39 H39 0.96(2) . ? C40 C41 1.373(3) . ? C40 H40 0.96(3) . ? C41 C42 1.383(3) . ? C41 H41 0.99(3) . ? C42 C43 1.424(3) . ? C42 C45 1.492(3) . ? C43 C44 1.483(3) . ? C44 H44A 0.94(3) . ? C44 H44B 0.94(3) . ? C44 H44C 0.94(3) . ? C45 H45A 1.02(3) . ? C45 H45B 0.99(3) . ? C45 H45C 1.04(4) . ? OM CM 1.401(4) . ? OM H1OM 0.84(4) . ? CM H1M 1.02(4) . ? CM H2M 0.90(4) . ? CM H3M 0.97(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 O31 Cu N1 168.95(5) . . ? O31 Cu N3 93.38(6) . . ? N1 Cu N3 91.96(6) . . ? O31 Cu O11 88.16(5) . . ? N1 Cu O11 89.91(5) . . ? N3 Cu O11 161.20(5) . . ? C5 N1 C1 117.08(15) . . ? C5 N1 Cu 124.70(11) . . ? C1 N1 Cu 117.81(12) . . ? C5 N2 C6 131.95(15) . . ? C5 N2 H2N 112.9(15) . . ? C6 N2 H2N 114.2(15) . . ? C6 N3 C10 116.83(15) . . ? C6 N3 Cu 123.99(12) . . ? C10 N3 Cu 119.03(12) . . ? C2 C1 N1 124.04(18) . . ? C2 C1 H1 123.6(13) . . ? N1 C1 H1 112.4(13) . . ? C1 C2 C3 118.09(18) . . ? C1 C2 H2 120.2(14) . . ? C3 C2 H2 121.7(14) . . ? C4 C3 C2 119.45(18) . . ? C4 C3 H3 121.0(13) . . ? C2 C3 H3 119.6(13) . . ? C3 C4 C5 119.23(17) . . ? C3 C4 H4 121.4(13) . . ? C5 C4 H4 119.4(13) . . ? N1 C5 N2 120.66(15) . . ? N1 C5 C4 121.91(15) . . ? N2 C5 C4 117.42(15) . . ? N3 C6 N2 121.50(15) . . ? N3 C6 C7 121.91(16) . . ? N2 C6 C7 116.59(16) . . ? C8 C7 C6 119.88(18) . . ? C8 C7 H7 121.9(14) . . ? C6 C7 H7 118.1(14) . . ? C7 C8 C9 118.78(18) . . ? C7 C8 H8 118.8(15) . . ? C9 C8 H8 122.4(15) . . ? C10 C9 C8 118.6(2) . . ? C10 C9 H9 117.6(16) . . ? C8 C9 H9 123.8(16) . . ? N3 C10 C9 123.97(19) . . ? N3 C10 H10 116.8(14) . . ? C9 C10 H10 119.2(14) . . ? C17 N11 C18 124.03(15) . . ? C17 N11 H11N 115.6(16) . . ? C18 N11 H11N 120.2(16) . . ? C11 O11 Cu 101.78(10) . . ? O12 C11 O11 120.82(16) . . ? O12 C11 C12 119.88(15) . . ? O11 C11 C12 119.26(14) . . ? C13 C12 C17 119.08(16) . . ? C13 C12 C11 117.97(15) . . ? C17 C12 C11 122.86(15) . . ? C14 C13 C12 121.95(17) . . ? C14 C13 H13 121.2(12) . . ? C12 C13 H13 116.8(12) . . ? C13 C14 C15 118.80(17) . . ? C13 C14 H14 121.5(13) . . ? C15 C14 H14 119.7(13) . . ? C16 C15 C14 120.84(18) . . ? C16 C15 H15 119.3(14) . . ? C14 C15 H15 119.8(14) . . ? C15 C16 C17 121.34(17) . . ? C15 C16 H16 120.5(13) . . ? C17 C16 H16 118.2(13) . . ? N11 C17 C16 119.90(16) . . ? N11 C17 C12 122.12(16) . . ? C16 C17 C12 117.98(16) . . ? C19 C18 C23 121.42(17) . . ? C19 C18 N11 118.64(18) . . ? C23 C18 N11 119.94(17) . . ? C18 C19 C20 119.5(2) . . ? C18 C19 H19 119.3(14) . . ? C20 C19 H19 121.2(14) . . ? C21 C20 C19 119.8(2) . . ? C21 C20 H20 122.4(14) . . ? C19 C20 H20 117.8(14) . . ? C20 C21 C22 121.64(18) . . ? C20 C21 H21 119.7(13) . . ? C22 C21 H21 118.6(13) . . ? C21 C22 C23 119.2(2) . . ? C21 C22 C24 120.8(2) . . ? C23 C22 C24 120.0(2) . . ? C18 C23 C22 118.39(18) . . ? C18 C23 C25 121.24(17) . . ? C22 C23 C25 120.36(19) . . ? C22 C24 H24A 109.3(17) . . ? C22 C24 H24B 110.9(14) . . ? H24A C24 H24B 107(2) . . ? C22 C24 H24C 114.6(17) . . ? H24A C24 H24C 106(2) . . ? H24B C24 H24C 109(2) . . ? C23 C25 H25A 110.6(15) . . ? C23 C25 H25B 111.1(16) . . ? H25A C25 H25B 106(2) . . ? C23 C25 H25C 111.5(17) . . ? H25A C25 H25C 110(2) . . ? H25B C25 H25C 107(2) . . ? C37 N31 C38 122.98(17) . . ? C37 N31 H31N 115.1(16) . . ? C38 N31 H31N 119.3(16) . . ? C31 O31 Cu 105.79(11) . . ? O32 C31 O31 120.72(16) . . ? O32 C31 C32 122.55(16) . . ? O31 C31 C32 116.70(16) . . ? C33 C32 C37 118.96(17) . . ? C33 C32 C31 118.93(16) . . ? C37 C32 C31 122.04(16) . . ? C34 C33 C32 122.13(18) . . ? C34 C33 H33 121.0(14) . . ? C32 C33 H33 116.8(13) . . ? C33 C34 C35 119.0(2) . . ? C33 C34 H34 122.3(15) . . ? C35 C34 H34 118.8(15) . . ? C36 C35 C34 120.7(2) . . ? C36 C35 H35 119.2(18) . . ? C34 C35 H35 120.0(18) . . ? C35 C36 C37 121.32(19) . . ? C35 C36 H36 119.8(13) . . ? C37 C36 H36 118.9(13) . . ? N31 C37 C36 120.81(17) . . ? N31 C37 C32 121.25(17) . . ? C36 C37 C32 117.94(17) . . ? C39 C38 C43 121.89(19) . . ? C39 C38 N31 118.83(19) . . ? C43 C38 N31 119.27(18) . . ? C38 C39 C40 119.5(2) . . ? C38 C39 H39 111.5(12) . . ? C40 C39 H39 128.9(12) . . ? C41 C40 C39 119.2(2) . . ? C41 C40 H40 118.3(15) . . ? C39 C40 H40 122.5(15) . . ? C40 C41 C42 122.5(2) . . ? C40 C41 H41 117.2(15) . . ? C42 C41 H41 120.3(15) . . ? C41 C42 C43 118.50(19) . . ? C41 C42 C45 121.8(2) . . ? C43 C42 C45 119.64(19) . . ? C38 C43 C42 118.35(19) . . ? C38 C43 C44 122.39(19) . . ? C42 C43 C44 119.25(19) . . ? C43 C44 H44A 106.4(18) . . ? C43 C44 H44B 110.9(18) . . ? H44A C44 H44B 115(2) . . ? C43 C44 H44C 110.8(17) . . ? H44A C44 H44C 108(2) . . ? H44B C44 H44C 106(2) . . ? C42 C45 H45A 111.0(16) . . ? C42 C45 H45B 108.9(16) . . ? H45A C45 H45B 111(2) . . ? C42 C45 H45C 109(2) . . ? H45A C45 H45C 106(3) . . ? H45B C45 H45C 110(3) . . ? CM OM H1OM 111(2) . . ? OM CM H1M 112(2) . . ? OM CM H2M 108(2) . . ? H1M CM H2M 107(3) . . ? OM CM H3M 113(2) . . ? H1M CM H3M 100(3) . . ? H2M CM H3M 117(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.510 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.045