Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Lutz Gade' _publ_contact_author_address ; Anorganisch-Chemisches Institut University of Heidelberg Im Neuenheimer Feld 270 Heidelberg 69120 GERMANY ; _publ_contact_author_email LUTZ.GADE@UNI-HD.DE _publ_section_title ; Bisoxazolines with One and Two Sidearms: Stereodirecting Ligands for Copper-Catalysed Asymmetric Allylic Oxidations of Alkenes ; loop_ _publ_author_name 'Lutz Gade' 'Stephane Bellemin-Laponnaz' 'Carmine Capacchione' 'Markus Seitz' 'Hubert Wadepohl' data_ga_ms1a _database_code_depnum_ccdc_archive 'CCDC 283311' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H35 N3 O4 S' _chemical_formula_weight 449.60 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.5200(4) _cell_length_b 19.3181(11) _cell_length_c 9.6743(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.0890(10) _cell_angle_gamma 90.00 _cell_volume 1170.79(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9502 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18426 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 32.01 _reflns_number_total 6926 _reflns_number_gt 5873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0453P)^2^+0.5615P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(6) _refine_ls_number_reflns 6926 _refine_ls_number_parameters 354 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.126 _refine_ls_shift/su_mean 0.005 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 0.5449(3) 0.75197(10) 0.3876(2) 0.0216(4) Uani 1 1 d . . . C2 C 0.5399(3) 0.67643(10) 0.3395(2) 0.0180(3) Uani 1 1 d . . . C3 C 0.7507(3) 0.65339(10) 0.31008(19) 0.0182(3) Uani 1 1 d . . . C4 C 0.9392(3) 0.65803(11) 0.44542(19) 0.0217(4) Uani 1 1 d . . . H4A H 1.0681 0.6403 0.4243 0.033 Uiso 1 1 calc R . . H4B H 0.9087 0.6303 0.5222 0.033 Uiso 1 1 calc R . . H4C H 0.9614 0.7064 0.4764 0.033 Uiso 1 1 calc R . . C5 C 0.7276(3) 0.57907(11) 0.2565(2) 0.0214(4) Uani 1 1 d . . . C6 C 0.6197(4) 0.47678(11) 0.1646(2) 0.0265(4) Uani 1 1 d . . . C7 C 0.8610(5) 0.47840(16) 0.2076(4) 0.0512(8) Uani 1 1 d . . . C8 C 0.5086(5) 0.47215(12) 0.0043(2) 0.0334(5) Uani 1 1 d . . . C9 C 0.5804(5) 0.40778(13) -0.0637(3) 0.0421(6) Uani 1 1 d . . . H9A H 0.7332 0.4113 -0.0558 0.063 Uiso 1 1 calc R . . H9B H 0.4997 0.4048 -0.1653 0.063 Uiso 1 1 calc R . . H9C H 0.5541 0.3662 -0.0131 0.063 Uiso 1 1 calc R . . C10 C 0.2719(6) 0.4724(2) -0.0263(5) 0.0736(13) Uani 1 1 d . . . H10A H 0.2270 0.4330 0.0221 0.110 Uiso 1 1 calc R . . H10B H 0.2069 0.4688 -0.1303 0.110 Uiso 1 1 calc R . . H10C H 0.2260 0.5156 0.0093 0.110 Uiso 1 1 calc R . . C11 C 0.7908(3) 0.69675(10) 0.18883(18) 0.0173(3) Uani 1 1 d . . . C12 C 0.6942(4) 0.73994(12) -0.0354(2) 0.0237(4) Uani 1 1 d . . . C13 C 0.9209(3) 0.76297(10) 0.0461(2) 0.0206(4) Uani 1 1 d . . . C14 C 1.0955(3) 0.73539(12) -0.0177(2) 0.0230(4) Uani 1 1 d . . . C15 C 1.0940(4) 0.65631(12) -0.0279(2) 0.0281(4) Uani 1 1 d . . . H15A H 0.9626 0.6411 -0.0982 0.042 Uiso 1 1 calc R . . H15B H 1.1005 0.6364 0.0665 0.042 Uiso 1 1 calc R . . H15C H 1.2178 0.6408 -0.0583 0.042 Uiso 1 1 calc R . . C16 C 1.0746(4) 0.76793(15) -0.1651(2) 0.0336(5) Uani 1 1 d . . . H16A H 1.1902 0.7511 -0.2030 0.050 Uiso 1 1 calc R . . H16B H 1.0836 0.8184 -0.1555 0.050 Uiso 1 1 calc R . . H16C H 0.9367 0.7551 -0.2312 0.050 Uiso 1 1 calc R . . C19 C 0.3962(3) 0.90853(10) 0.4672(2) 0.0204(4) Uani 1 1 d . . . C20 C 0.6072(4) 0.93018(11) 0.4998(2) 0.0252(4) Uani 1 1 d . . . C21 C 0.6549(4) 0.99330(12) 0.4458(2) 0.0293(5) Uani 1 1 d . . . C22 C 0.4940(4) 1.03449(11) 0.3598(2) 0.0273(4) Uani 1 1 d . . . C23 C 0.2843(4) 1.01156(12) 0.3293(2) 0.0296(5) Uani 1 1 d . . . C24 C 0.2333(4) 0.94916(12) 0.3816(2) 0.0262(4) Uani 1 1 d . . . C25 C 0.5463(5) 1.10230(12) 0.2997(2) 0.0369(6) Uani 1 1 d . . . H25A H 0.4696 1.1053 0.1973 0.055 Uiso 1 1 calc R . . H25B H 0.7003 1.1049 0.3115 0.055 Uiso 1 1 calc R . . H25C H 0.5029 1.1408 0.3515 0.055 Uiso 1 1 calc R . . H6 H 0.576(5) 0.4355(17) 0.215(3) 0.040(8) Uiso 1 1 d . . . H8 H 0.572(5) 0.5146(17) -0.047(3) 0.043(8) Uiso 1 1 d . . . H11 H 0.226(4) 0.7672(14) 0.339(3) 0.028(7) Uiso 1 1 d . . . H13 H 0.933(4) 0.8122(14) 0.054(3) 0.026(6) Uiso 1 1 d . . . H14 H 1.220(4) 0.7476(13) 0.045(2) 0.015(5) Uiso 1 1 d . . . H20 H 0.724(4) 0.9036(16) 0.565(3) 0.031(7) Uiso 1 1 d . . . H21 H 0.795(6) 1.000(2) 0.469(4) 0.055(10) Uiso 1 1 d . . . H23 H 0.171(5) 1.0357(16) 0.270(3) 0.033(7) Uiso 1 1 d . . . H24 H 0.091(5) 0.9335(15) 0.358(3) 0.033(7) Uiso 1 1 d . . . H1A H 0.661(4) 0.7584(15) 0.476(3) 0.029(7) Uiso 1 1 d . . . H2A H 0.423(4) 0.6693(13) 0.250(3) 0.019(6) Uiso 1 1 d . . . H7A H 0.949(8) 0.448(3) 0.301(5) 0.110(17) Uiso 1 1 d . . . H12A H 0.590(4) 0.7759(15) -0.058(3) 0.028(7) Uiso 1 1 d . . . H1B H 0.572(4) 0.7831(14) 0.321(3) 0.025(6) Uiso 1 1 d . . . H2B H 0.511(4) 0.6463(14) 0.417(3) 0.024(6) Uiso 1 1 d . . . H7B H 0.891(5) 0.4764(17) 0.123(3) 0.038(8) Uiso 1 1 d . . . H12B H 0.685(4) 0.7185(14) -0.122(3) 0.026(6) Uiso 1 1 d . . . N1 N 0.3433(3) 0.76861(9) 0.41884(18) 0.0201(3) Uani 1 1 d . . . N2 N 0.5601(3) 0.54272(9) 0.22281(19) 0.0250(4) Uani 1 1 d . . . N3 N 0.9500(3) 0.73554(8) 0.19406(16) 0.0189(3) Uani 1 1 d . . . O1 O 0.4981(3) 0.81474(7) 0.66333(14) 0.0252(3) Uani 1 1 d . . . O2 O 0.1142(2) 0.83169(9) 0.53604(14) 0.0255(3) Uani 1 1 d . . . O3 O 0.9139(3) 0.55151(9) 0.2437(2) 0.0407(4) Uani 1 1 d . . . O4 O 0.6354(2) 0.69145(8) 0.06251(14) 0.0232(3) Uani 1 1 d . . . S1 S 0.33252(8) 0.82807(2) 0.53330(4) 0.01884(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0207(10) 0.0183(9) 0.0272(9) -0.0032(7) 0.0093(8) -0.0019(7) C2 0.0203(9) 0.0153(8) 0.0193(8) 0.0001(6) 0.0070(7) -0.0013(7) C3 0.0205(9) 0.0143(8) 0.0198(8) 0.0018(6) 0.0057(7) 0.0005(7) C4 0.0224(10) 0.0220(9) 0.0197(8) 0.0030(7) 0.0040(7) -0.0015(8) C5 0.0248(10) 0.0179(9) 0.0213(8) 0.0020(7) 0.0064(7) 0.0043(7) C6 0.0414(13) 0.0138(8) 0.0249(9) 0.0008(7) 0.0103(9) 0.0014(8) C7 0.0431(17) 0.0299(14) 0.074(2) -0.0227(14) 0.0056(16) 0.0087(12) C8 0.0510(15) 0.0168(9) 0.0283(10) -0.0017(8) 0.0044(10) 0.0056(10) C9 0.075(2) 0.0221(11) 0.0304(11) -0.0022(9) 0.0176(12) 0.0059(12) C10 0.048(2) 0.050(2) 0.101(3) -0.043(2) -0.0154(19) 0.0133(16) C11 0.0181(9) 0.0169(8) 0.0175(7) -0.0003(6) 0.0058(7) 0.0024(7) C12 0.0257(11) 0.0275(10) 0.0189(8) 0.0054(7) 0.0077(7) 0.0013(8) C13 0.0256(10) 0.0180(9) 0.0196(8) 0.0025(6) 0.0084(7) -0.0003(8) C14 0.0204(10) 0.0302(10) 0.0188(8) 0.0010(7) 0.0062(7) -0.0026(8) C15 0.0253(11) 0.0310(11) 0.0286(10) -0.0064(8) 0.0087(8) 0.0038(9) C16 0.0315(12) 0.0490(15) 0.0228(9) 0.0055(9) 0.0118(9) -0.0059(11) C19 0.0276(11) 0.0155(8) 0.0185(8) 0.0007(6) 0.0071(7) 0.0010(7) C20 0.0282(11) 0.0201(9) 0.0240(9) 0.0021(7) 0.0019(8) -0.0019(8) C21 0.0349(13) 0.0232(10) 0.0286(10) 0.0010(8) 0.0066(9) -0.0081(9) C22 0.0417(14) 0.0166(9) 0.0230(9) -0.0012(7) 0.0082(9) -0.0030(9) C23 0.0372(13) 0.0214(10) 0.0302(10) 0.0060(8) 0.0093(9) 0.0065(9) C24 0.0271(12) 0.0251(10) 0.0267(9) 0.0035(8) 0.0079(8) 0.0022(9) C25 0.0592(17) 0.0211(10) 0.0270(10) 0.0040(8) 0.0065(11) -0.0079(11) N1 0.0197(8) 0.0206(8) 0.0213(7) -0.0055(6) 0.0077(6) -0.0020(7) N2 0.0335(10) 0.0168(8) 0.0276(8) -0.0044(6) 0.0134(7) -0.0032(7) N3 0.0221(8) 0.0176(7) 0.0179(6) -0.0005(5) 0.0073(6) -0.0010(6) O1 0.0374(9) 0.0188(7) 0.0185(6) 0.0002(5) 0.0065(6) -0.0010(6) O2 0.0303(8) 0.0220(7) 0.0291(6) 0.0004(6) 0.0165(6) 0.0011(7) O3 0.0251(9) 0.0253(8) 0.0692(12) -0.0164(8) 0.0089(8) 0.0051(7) O4 0.0199(7) 0.0278(8) 0.0206(6) 0.0051(5) 0.0035(5) -0.0025(6) S1 0.0251(2) 0.01570(19) 0.01703(17) -0.00041(17) 0.00804(16) 0.0001(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 C1 N1 1.464(3) . ? C1 C2 1.529(3) . ? C2 C3 1.544(3) . ? C3 C5 1.520(3) . ? C3 C11 1.522(2) . ? C3 C4 1.530(3) . ? C5 N2 1.263(3) . ? C5 O3 1.363(3) . ? C6 N2 1.487(3) . ? C6 C7 1.512(4) . ? C6 C8 1.522(3) . ? C7 O3 1.473(3) . ? C8 C10 1.488(5) . ? C8 C9 1.539(3) . ? C11 N3 1.270(2) . ? C11 O4 1.358(2) . ? C12 O4 1.457(2) . ? C12 C13 1.536(3) . ? C13 N3 1.488(2) . ? C13 C14 1.533(3) . ? C14 C15 1.531(3) . ? C14 C16 1.529(3) . ? C19 C20 1.388(3) . ? C19 C24 1.394(3) . ? C19 S1 1.773(2) . ? C20 C21 1.395(3) . ? C21 C22 1.394(3) . ? C22 C23 1.389(3) . ? C22 C25 1.510(3) . ? C23 C24 1.383(3) . ? N1 S1 1.6105(16) . ? O1 S1 1.4358(15) . ? O2 S1 1.4326(15) . ? 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 N1 C1 C2 109.14(16) . . ? C1 C2 C3 112.73(16) . . ? C5 C3 C11 106.19(15) . . ? C5 C3 C4 109.11(16) . . ? C11 C3 C4 111.00(16) . . ? C5 C3 C2 109.06(16) . . ? C11 C3 C2 109.59(15) . . ? C4 C3 C2 111.72(15) . . ? N2 C5 O3 119.24(19) . . ? N2 C5 C3 127.57(19) . . ? O3 C5 C3 113.18(18) . . ? N2 C6 C7 103.83(19) . . ? N2 C6 C8 109.61(17) . . ? C7 C6 C8 116.5(2) . . ? O3 C7 C6 104.0(2) . . ? C10 C8 C6 112.1(3) . . ? C10 C8 C9 109.8(2) . . ? C6 C8 C9 111.6(2) . . ? N3 C11 O4 118.56(16) . . ? N3 C11 C3 127.39(17) . . ? O4 C11 C3 114.04(16) . . ? O4 C12 C13 103.97(15) . . ? N3 C13 C12 103.83(15) . . ? N3 C13 C14 110.64(16) . . ? C12 C13 C14 114.12(17) . . ? C15 C14 C16 110.66(18) . . ? C15 C14 C13 112.36(17) . . ? C16 C14 C13 110.39(18) . . ? C20 C19 C24 120.61(19) . . ? C20 C19 S1 119.94(16) . . ? C24 C19 S1 119.45(17) . . ? C19 C20 C21 119.2(2) . . ? C22 C21 C20 120.9(2) . . ? C23 C22 C21 118.6(2) . . ? C23 C22 C25 120.6(2) . . ? C21 C22 C25 120.8(2) . . ? C24 C23 C22 121.5(2) . . ? C23 C24 C19 119.2(2) . . ? C1 N1 S1 120.75(14) . . ? C5 N2 C6 106.01(19) . . ? C11 N3 C13 106.66(16) . . ? C5 O3 C7 103.9(2) . . ? C11 O4 C12 105.76(15) . . ? O1 S1 O2 120.14(8) . . ? O1 S1 N1 108.00(9) . . ? O2 S1 N1 106.28(9) . . ? O1 S1 C19 106.18(9) . . ? O2 S1 C19 107.29(10) . . ? N1 S1 C19 108.56(9) . . ? 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 N1 C1 C2 C3 -177.68(15) . . . . ? C1 C2 C3 C5 -177.40(16) . . . . ? C1 C2 C3 C11 -61.6(2) . . . . ? C1 C2 C3 C4 61.9(2) . . . . ? C11 C3 C5 N2 -109.9(2) . . . . ? C4 C3 C5 N2 130.4(2) . . . . ? C2 C3 C5 N2 8.2(3) . . . . ? C11 C3 C5 O3 69.3(2) . . . . ? C4 C3 C5 O3 -50.4(2) . . . . ? C2 C3 C5 O3 -172.70(17) . . . . ? N2 C6 C7 O3 -17.0(3) . . . . ? C8 C6 C7 O3 103.6(3) . . . . ? N2 C6 C8 C10 -61.3(3) . . . . ? C7 C6 C8 C10 -178.8(2) . . . . ? N2 C6 C8 C9 175.0(2) . . . . ? C7 C6 C8 C9 57.5(3) . . . . ? C5 C3 C11 N3 -122.0(2) . . . . ? C4 C3 C11 N3 -3.5(3) . . . . ? C2 C3 C11 N3 120.4(2) . . . . ? C5 C3 C11 O4 57.6(2) . . . . ? C4 C3 C11 O4 176.02(16) . . . . ? C2 C3 C11 O4 -60.1(2) . . . . ? O4 C12 C13 N3 -10.9(2) . . . . ? O4 C12 C13 C14 109.68(18) . . . . ? N3 C13 C14 C15 60.1(2) . . . . ? C12 C13 C14 C15 -56.5(2) . . . . ? N3 C13 C14 C16 -175.79(18) . . . . ? C12 C13 C14 C16 67.6(2) . . . . ? C24 C19 C20 C21 0.0(3) . . . . ? S1 C19 C20 C21 179.37(16) . . . . ? C19 C20 C21 C22 -0.2(3) . . . . ? C20 C21 C22 C23 0.3(3) . . . . ? C20 C21 C22 C25 -179.1(2) . . . . ? C21 C22 C23 C24 -0.3(3) . . . . ? C25 C22 C23 C24 179.1(2) . . . . ? C22 C23 C24 C19 0.2(3) . . . . ? C20 C19 C24 C23 0.0(3) . . . . ? S1 C19 C24 C23 -179.37(16) . . . . ? C2 C1 N1 S1 152.61(14) . . . . ? O3 C5 N2 C6 -4.3(3) . . . . ? C3 C5 N2 C6 174.84(18) . . . . ? C7 C6 N2 C5 13.4(3) . . . . ? C8 C6 N2 C5 -111.8(2) . . . . ? O4 C11 N3 C13 -3.0(2) . . . . ? C3 C11 N3 C13 176.55(17) . . . . ? C12 C13 N3 C11 8.6(2) . . . . ? C14 C13 N3 C11 -114.22(18) . . . . ? N2 C5 O3 C7 -7.1(3) . . . . ? C3 C5 O3 C7 173.7(2) . . . . ? C6 C7 O3 C5 14.7(3) . . . . ? N3 C11 O4 C12 -4.5(2) . . . . ? C3 C11 O4 C12 175.93(16) . . . . ? C13 C12 O4 C11 9.4(2) . . . . ? C1 N1 S1 O1 -50.78(18) . . . . ? C1 N1 S1 O2 179.06(15) . . . . ? C1 N1 S1 C19 63.93(18) . . . . ? C20 C19 S1 O1 27.10(18) . . . . ? C24 C19 S1 O1 -153.55(16) . . . . ? C20 C19 S1 O2 156.73(16) . . . . ? C24 C19 S1 O2 -23.91(18) . . . . ? C20 C19 S1 N1 -88.80(18) . . . . ? C24 C19 S1 N1 90.55(17) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 32.01 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.669 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.063 #===END data_ga_ms5aa _database_code_depnum_ccdc_archive 'CCDC 283312' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H37 Cu N3 O7' _chemical_formula_weight 543.11 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3854(12) _cell_length_b 14.6399(18) _cell_length_c 19.322(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2654.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 0.869 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8319 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29150 _diffrn_reflns_av_R_equivalents 0.1370 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4693 _reflns_number_gt 3740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1114P)^2^+4.9482P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(3) _refine_ls_number_reflns 4693 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2045 _refine_ls_wR_factor_gt 0.1926 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.9756(9) 1.0854(5) 0.8621(4) 0.0302(19) Uani 1 1 d . . . C2 C 0.8279(9) 1.1667(5) 0.7913(4) 0.0230(17) Uani 1 1 d . . . H2A H 0.8546 1.2101 0.7542 0.028 Uiso 1 1 calc R . . H2B H 0.7300 1.1807 0.8071 0.028 Uiso 1 1 calc R . . C3 C 0.8391(8) 1.0685(5) 0.7662(4) 0.0185(16) Uani 1 1 d . . . H3 H 0.8915 1.0674 0.7211 0.022 Uiso 1 1 calc R . . C4 C 0.6947(8) 1.0170(5) 0.7577(5) 0.0280(19) Uani 1 1 d . . . H4 H 0.7172 0.9523 0.7453 0.034 Uiso 1 1 calc R . . C5 C 0.6082(9) 1.0152(6) 0.8237(6) 0.048(3) Uani 1 1 d . . . H5A H 0.5917 1.0778 0.8396 0.072 Uiso 1 1 calc R . . H5B H 0.6603 0.9812 0.8593 0.072 Uiso 1 1 calc R . . H5C H 0.5165 0.9853 0.8149 0.072 Uiso 1 1 calc R . . C6 C 0.6130(10) 1.0577(6) 0.6983(6) 0.047(3) Uani 1 1 d . . . H6A H 0.5197 1.0280 0.6948 0.071 Uiso 1 1 calc R . . H6B H 0.6661 1.0484 0.6553 0.071 Uiso 1 1 calc R . . H6C H 0.5999 1.1233 0.7062 0.071 Uiso 1 1 calc R . . C7 C 1.0780(9) 0.9791(6) 0.9498(4) 0.0297(19) Uani 1 1 d . . . C8 C 1.1163(8) 0.8768(5) 1.0322(4) 0.0247(17) Uani 1 1 d . . . H8A H 1.0367 0.8667 1.0650 0.030 Uiso 1 1 calc R . . H8B H 1.2056 0.8541 1.0533 0.030 Uiso 1 1 calc R . . C9 C 1.0875(8) 0.8301(5) 0.9630(4) 0.0192(15) Uani 1 1 d . . . H9 H 1.0040 0.7883 0.9685 0.023 Uiso 1 1 calc R . . C10 C 1.2120(8) 0.7754(6) 0.9333(4) 0.0284(19) Uani 1 1 d . . . H10 H 1.1851 0.7576 0.8851 0.034 Uiso 1 1 calc R . . C11 C 1.3494(9) 0.8287(7) 0.9285(5) 0.037(2) Uani 1 1 d . . . H11A H 1.3341 0.8839 0.9008 0.055 Uiso 1 1 calc R . . H11B H 1.4227 0.7908 0.9066 0.055 Uiso 1 1 calc R . . H11C H 1.3807 0.8460 0.9751 0.055 Uiso 1 1 calc R . . C12 C 1.2262(9) 0.6864(6) 0.9753(5) 0.040(2) Uani 1 1 d . . . H12A H 1.3057 0.6502 0.9571 0.059 Uiso 1 1 calc R . . H12B H 1.1378 0.6511 0.9715 0.059 Uiso 1 1 calc R . . H12C H 1.2440 0.7012 1.0240 0.059 Uiso 1 1 calc R . . C13 C 1.0824(9) 1.0765(5) 0.9193(5) 0.031(2) Uani 1 1 d . . . C14 C 1.0537(11) 1.1462(6) 0.9766(5) 0.040(2) Uani 1 1 d . . . H14A H 1.1335 1.1443 1.0101 0.048 Uiso 1 1 calc R . . H14B H 1.0519 1.2081 0.9560 0.048 Uiso 1 1 calc R . . C15 C 0.9195(11) 1.1313(6) 1.0143(5) 0.037(2) Uani 1 1 d . . . C16 C 0.8939(12) 1.1688(7) 1.0809(5) 0.046(2) Uani 1 1 d . . . H16 H 0.9645 1.2058 1.1022 0.055 Uiso 1 1 calc R . . C17 C 0.7694(13) 1.1522(7) 1.1143(5) 0.048(3) Uani 1 1 d . . . H17 H 0.7534 1.1754 1.1596 0.057 Uiso 1 1 calc R . . C18 C 0.6643(13) 1.0997(8) 1.0806(6) 0.060(3) Uani 1 1 d . . . H18 H 0.5751 1.0876 1.1020 0.072 Uiso 1 1 calc R . . C19 C 0.6954(11) 1.0661(7) 1.0146(5) 0.044(2) Uani 1 1 d . . . H19 H 0.6244 1.0315 0.9914 0.053 Uiso 1 1 calc R . . C20 C 1.2326(9) 1.0911(7) 0.8883(5) 0.039(2) Uani 1 1 d . . . H20A H 1.2528 1.0427 0.8547 0.059 Uiso 1 1 calc R . . H20B H 1.3036 1.0891 0.9255 0.059 Uiso 1 1 calc R . . H20C H 1.2365 1.1506 0.8652 0.059 Uiso 1 1 calc R . . C21 C 0.8368(7) 0.7451(5) 0.8138(4) 0.0222(16) Uani 1 1 d . . . C22 C 0.8019(9) 0.6437(5) 0.8028(4) 0.029(2) Uani 1 1 d . . . H22A H 0.6983 0.6356 0.8006 0.043 Uiso 1 1 calc R . . H22B H 0.8402 0.6079 0.8414 0.043 Uiso 1 1 calc R . . H22C H 0.8448 0.6227 0.7594 0.043 Uiso 1 1 calc R . . C23 C 1.1574(8) 0.8991(6) 0.7154(4) 0.0229(16) Uani 1 1 d . . . C24 C 1.2194(8) 0.8953(7) 0.6432(4) 0.0326(19) Uani 1 1 d . . . H24A H 1.3203 0.8785 0.6458 0.049 Uiso 1 1 calc R . . H24B H 1.2102 0.9553 0.6212 0.049 Uiso 1 1 calc R . . H24C H 1.1679 0.8497 0.6157 0.049 Uiso 1 1 calc R . . Cu1 Cu 0.98676(8) 0.89665(6) 0.81991(4) 0.0189(2) Uani 1 1 d . . . N1 N 0.9289(7) 1.0244(4) 0.8207(4) 0.0229(13) Uani 1 1 d . . . N2 N 1.0459(6) 0.9065(4) 0.9176(3) 0.0217(14) Uani 1 1 d . . . N3 N 0.8179(9) 1.0797(5) 0.9827(4) 0.0397(19) Uani 1 1 d . . . O1 O 0.9306(7) 1.1711(4) 0.8497(3) 0.0353(14) Uani 1 1 d . . . O2 O 1.1282(7) 0.9713(4) 1.0142(3) 0.0366(15) Uani 1 1 d . . . O3 O 0.7415(6) 0.8024(4) 0.8128(4) 0.0406(15) Uani 1 1 d . . . O4 O 0.9670(5) 0.7640(3) 0.8232(3) 0.0247(11) Uani 1 1 d . . . O5 O 1.0201(5) 0.8979(4) 0.7188(2) 0.0268(11) Uani 1 1 d . . . O6 O 1.2346(5) 0.9005(4) 0.7671(3) 0.0279(12) Uani 1 1 d . . . O7 O 0.4753(6) 0.7848(4) 0.7438(3) 0.0383(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.034(4) 0.025(4) 0.032(4) 0.000(3) 0.012(4) 0.010(4) C2 0.028(4) 0.015(4) 0.026(4) 0.002(3) -0.001(3) -0.001(3) C3 0.019(4) 0.017(4) 0.019(4) 0.005(3) -0.001(3) -0.003(3) C4 0.023(4) 0.014(4) 0.047(5) -0.002(4) -0.006(4) -0.003(3) C5 0.028(4) 0.033(5) 0.083(8) -0.011(6) 0.018(6) -0.005(4) C6 0.039(5) 0.028(5) 0.075(8) -0.009(5) -0.039(5) 0.002(4) C7 0.030(5) 0.030(5) 0.029(5) 0.004(4) -0.007(4) -0.002(4) C8 0.026(4) 0.024(4) 0.024(4) 0.001(3) -0.001(3) -0.002(3) C9 0.019(3) 0.019(4) 0.020(4) 0.010(3) 0.004(3) -0.003(3) C10 0.018(4) 0.036(5) 0.031(4) -0.001(4) 0.000(3) 0.005(3) C11 0.026(4) 0.049(6) 0.036(5) 0.018(4) -0.004(4) -0.001(4) C12 0.018(4) 0.033(5) 0.068(7) 0.001(5) -0.007(4) 0.013(4) C13 0.033(4) 0.017(4) 0.042(5) -0.002(4) -0.007(4) -0.003(3) C14 0.069(7) 0.019(4) 0.032(5) -0.008(4) -0.014(5) 0.004(4) C15 0.057(6) 0.019(4) 0.035(5) -0.008(4) -0.011(5) 0.011(4) C16 0.068(7) 0.032(5) 0.038(5) -0.003(4) -0.001(5) 0.013(5) C17 0.079(8) 0.036(6) 0.028(5) 0.005(4) 0.007(5) 0.025(6) C18 0.072(7) 0.053(7) 0.055(7) 0.008(6) 0.030(6) 0.033(7) C19 0.043(6) 0.042(5) 0.048(6) 0.007(5) -0.003(5) 0.003(4) C20 0.031(4) 0.041(6) 0.046(5) 0.002(5) -0.008(4) 0.000(4) C21 0.021(4) 0.017(4) 0.029(4) 0.003(4) 0.001(4) 0.003(3) C22 0.034(4) 0.023(4) 0.030(5) -0.006(3) 0.008(3) -0.004(3) C23 0.026(4) 0.014(4) 0.028(4) 0.003(4) 0.002(3) 0.009(4) C24 0.032(4) 0.036(5) 0.030(4) 0.004(4) 0.009(3) 0.001(5) Cu1 0.0184(4) 0.0190(4) 0.0194(4) 0.0010(4) -0.0028(4) -0.0008(4) N1 0.031(3) 0.018(3) 0.020(3) 0.001(3) -0.010(3) -0.005(2) N2 0.022(3) 0.022(3) 0.021(3) -0.001(3) -0.004(2) -0.004(3) N3 0.048(5) 0.037(5) 0.035(4) -0.008(3) 0.002(4) 0.009(3) O1 0.046(3) 0.021(3) 0.039(3) -0.001(3) -0.009(3) 0.004(3) O2 0.050(4) 0.035(3) 0.025(3) -0.002(3) -0.007(3) 0.003(3) O3 0.022(3) 0.027(3) 0.073(5) 0.000(3) -0.002(3) 0.003(2) O4 0.017(2) 0.023(3) 0.035(3) 0.000(3) -0.007(3) -0.0023(19) O5 0.023(3) 0.033(3) 0.025(2) 0.000(2) -0.001(2) -0.005(3) O6 0.020(2) 0.038(3) 0.026(3) -0.005(3) -0.001(2) 0.001(3) O7 0.027(3) 0.036(3) 0.052(4) 0.002(3) -0.004(3) -0.002(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 C1 N1 1.276(10) . ? C1 O1 1.345(10) . ? C1 C13 1.498(12) . ? C2 O1 1.486(10) . ? C2 C3 1.520(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.496(9) . ? C3 C4 1.560(10) . ? C3 H3 1.0000 . ? C4 C6 1.504(12) . ? C4 C5 1.511(13) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.268(10) . ? C7 O2 1.335(10) . ? C7 C13 1.543(12) . ? C8 O2 1.431(10) . ? C8 C9 1.527(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.475(9) . ? C9 C10 1.528(11) . ? C9 H9 1.0000 . ? C10 C11 1.510(12) . ? C10 C12 1.541(12) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.531(12) . ? C13 C20 1.546(12) . ? C14 C15 1.471(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.361(12) . ? C15 C16 1.419(13) . ? C16 C17 1.357(15) . ? C16 H16 0.9500 . ? C17 C18 1.410(17) . ? C17 H17 0.9500 . ? C18 C19 1.397(15) . ? C18 H18 0.9500 . ? C19 N3 1.319(13) . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O3 1.226(9) . ? C21 O4 1.266(9) . ? C21 C22 1.536(10) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O6 1.235(9) . ? C23 O5 1.291(9) . ? C23 C24 1.513(10) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? Cu1 N1 1.947(6) . ? Cu1 O4 1.952(5) . ? Cu1 N2 1.973(6) . ? Cu1 O5 1.978(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 O1 115.7(7) . . ? N1 C1 C13 129.2(7) . . ? O1 C1 C13 115.0(7) . . ? O1 C2 C3 103.8(6) . . ? O1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? O1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? N1 C3 C2 102.9(6) . . ? N1 C3 C4 110.7(6) . . ? C2 C3 C4 115.5(6) . . ? N1 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C6 C4 C5 112.1(8) . . ? C6 C4 C3 109.3(7) . . ? C5 C4 C3 112.8(7) . . ? C6 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C3 C4 H4 107.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 O2 118.0(7) . . ? N2 C7 C13 126.4(7) . . ? O2 C7 C13 115.2(7) . . ? O2 C8 C9 103.5(6) . . ? O2 C8 H8A 111.1 . . ? C9 C8 H8A 111.1 . . ? O2 C8 H8B 111.1 . . ? C9 C8 H8B 111.1 . . ? H8A C8 H8B 109.0 . . ? N2 C9 C8 103.1(6) . . ? N2 C9 C10 112.2(6) . . ? C8 C9 C10 115.4(6) . . ? N2 C9 H9 108.6 . . ? C8 C9 H9 108.6 . . ? C10 C9 H9 108.6 . . ? C11 C10 C9 113.9(7) . . ? C11 C10 C12 113.3(7) . . ? C9 C10 C12 108.2(7) . . ? C11 C10 H10 107.0 . . ? C9 C10 H10 107.0 . . ? C12 C10 H10 107.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C13 C14 111.0(7) . . ? C1 C13 C7 110.1(7) . . ? C14 C13 C7 109.6(7) . . ? C1 C13 C20 108.2(7) . . ? C14 C13 C20 110.4(7) . . ? C7 C13 C20 107.4(7) . . ? C15 C14 C13 114.2(8) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N3 C15 C16 120.1(10) . . ? N3 C15 C14 117.4(8) . . ? C16 C15 C14 122.4(9) . . ? C17 C16 C15 120.5(10) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 118.7(9) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C19 C18 C17 117.8(10) . . ? C19 C18 H18 121.1 . . ? C17 C18 H18 121.1 . . ? N3 C19 C18 123.8(10) . . ? N3 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 O4 123.8(7) . . ? O3 C21 C22 120.3(7) . . ? O4 C21 C22 115.9(6) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O6 C23 O5 122.9(7) . . ? O6 C23 C24 121.5(6) . . ? O5 C23 C24 115.6(7) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N1 Cu1 O4 158.2(2) . . ? N1 Cu1 N2 90.0(3) . . ? O4 Cu1 N2 94.0(3) . . ? N1 Cu1 O5 92.4(3) . . ? O4 Cu1 O5 93.2(2) . . ? N2 Cu1 O5 154.1(2) . . ? C1 N1 C3 109.4(6) . . ? C1 N1 Cu1 125.5(5) . . ? C3 N1 Cu1 124.5(5) . . ? C7 N2 C9 106.4(6) . . ? C7 N2 Cu1 126.7(6) . . ? C9 N2 Cu1 126.0(5) . . ? C19 N3 C15 119.0(8) . . ? C1 O1 C2 107.4(6) . . ? C7 O2 C8 106.4(6) . . ? C21 O4 Cu1 107.7(4) . . ? C23 O5 Cu1 102.1(4) . . ? 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 C2 C3 N1 9.1(7) . . . . ? O1 C2 C3 C4 129.8(7) . . . . ? N1 C3 C4 C6 -174.9(7) . . . . ? C2 C3 C4 C6 68.7(9) . . . . ? N1 C3 C4 C5 59.7(8) . . . . ? C2 C3 C4 C5 -56.7(9) . . . . ? O2 C8 C9 N2 -15.8(7) . . . . ? O2 C8 C9 C10 106.9(7) . . . . ? N2 C9 C10 C11 65.2(9) . . . . ? C8 C9 C10 C11 -52.5(9) . . . . ? N2 C9 C10 C12 -167.9(7) . . . . ? C8 C9 C10 C12 74.4(9) . . . . ? N1 C1 C13 C14 -151.1(9) . . . . ? O1 C1 C13 C14 34.2(10) . . . . ? N1 C1 C13 C7 -29.5(12) . . . . ? O1 C1 C13 C7 155.7(7) . . . . ? N1 C1 C13 C20 87.6(10) . . . . ? O1 C1 C13 C20 -87.1(8) . . . . ? N2 C7 C13 C1 30.2(12) . . . . ? O2 C7 C13 C1 -157.5(7) . . . . ? N2 C7 C13 C14 152.6(9) . . . . ? O2 C7 C13 C14 -35.1(10) . . . . ? N2 C7 C13 C20 -87.4(10) . . . . ? O2 C7 C13 C20 84.9(9) . . . . ? C1 C13 C14 C15 66.3(9) . . . . ? C7 C13 C14 C15 -55.6(9) . . . . ? C20 C13 C14 C15 -173.7(7) . . . . ? C13 C14 C15 N3 -20.0(11) . . . . ? C13 C14 C15 C16 160.1(8) . . . . ? N3 C15 C16 C17 1.2(14) . . . . ? C14 C15 C16 C17 -178.9(9) . . . . ? C15 C16 C17 C18 -2.2(14) . . . . ? C16 C17 C18 C19 1.2(15) . . . . ? C17 C18 C19 N3 0.9(16) . . . . ? O1 C1 N1 C3 2.6(10) . . . . ? C13 C1 N1 C3 -172.1(8) . . . . ? O1 C1 N1 Cu1 174.4(5) . . . . ? C13 C1 N1 Cu1 -0.3(13) . . . . ? C2 C3 N1 C1 -7.5(8) . . . . ? C4 C3 N1 C1 -131.5(7) . . . . ? C2 C3 N1 Cu1 -179.4(5) . . . . ? C4 C3 N1 Cu1 56.6(8) . . . . ? O4 Cu1 N1 C1 124.1(8) . . . . ? N2 Cu1 N1 C1 23.2(7) . . . . ? O5 Cu1 N1 C1 -131.0(7) . . . . ? O4 Cu1 N1 C3 -65.3(10) . . . . ? N2 Cu1 N1 C3 -166.2(6) . . . . ? O5 Cu1 N1 C3 39.6(6) . . . . ? O2 C7 N2 C9 -4.6(9) . . . . ? C13 C7 N2 C9 167.5(8) . . . . ? O2 C7 N2 Cu1 -174.0(5) . . . . ? C13 C7 N2 Cu1 -1.8(12) . . . . ? C8 C9 N2 C7 12.6(7) . . . . ? C10 C9 N2 C7 -112.1(8) . . . . ? C8 C9 N2 Cu1 -177.9(5) . . . . ? C10 C9 N2 Cu1 57.3(8) . . . . ? N1 Cu1 N2 C7 -22.1(7) . . . . ? O4 Cu1 N2 C7 179.3(7) . . . . ? O5 Cu1 N2 C7 73.6(9) . . . . ? N1 Cu1 N2 C9 170.5(6) . . . . ? O4 Cu1 N2 C9 11.9(6) . . . . ? O5 Cu1 N2 C9 -93.8(7) . . . . ? C18 C19 N3 C15 -2.0(14) . . . . ? C16 C15 N3 C19 0.9(13) . . . . ? C14 C15 N3 C19 -179.0(8) . . . . ? N1 C1 O1 C2 3.7(10) . . . . ? C13 C1 O1 C2 179.2(7) . . . . ? C3 C2 O1 C1 -8.1(8) . . . . ? N2 C7 O2 C8 -6.4(10) . . . . ? C13 C7 O2 C8 -179.4(7) . . . . ? C9 C8 O2 C7 13.7(8) . . . . ? O3 C21 O4 Cu1 -9.1(11) . . . . ? C22 C21 O4 Cu1 170.6(5) . . . . ? N1 Cu1 O4 C21 15.1(10) . . . . ? N2 Cu1 O4 C21 115.1(6) . . . . ? O5 Cu1 O4 C21 -89.7(6) . . . . ? O6 C23 O5 Cu1 -1.0(10) . . . . ? C24 C23 O5 Cu1 176.9(6) . . . . ? N1 Cu1 O5 C23 105.3(5) . . . . ? O4 Cu1 O5 C23 -95.8(5) . . . . ? N2 Cu1 O5 C23 10.1(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.916 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.112 #===END data_ga_ms3 _database_code_depnum_ccdc_archive 'CCDC 283313' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H41 Cu N3 O8 S' _chemical_formula_weight 631.23 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3203(6) _cell_length_b 10.7524(8) _cell_length_c 16.0394(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.198(2) _cell_angle_gamma 90.00 _cell_volume 1558.30(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 666 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8218 _exptl_absorpt_correction_T_max 0.9227 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13654 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6927 _reflns_number_gt 5658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0708P)^2^+0.9867P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(15) _refine_ls_number_reflns 6927 _refine_ls_number_parameters 371 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2529(5) 0.1438(4) 0.4074(3) 0.0308(9) Uani 1 1 d . . . C2 C 0.1890(6) 0.3197(5) 0.4617(3) 0.0450(12) Uani 1 1 d . . . H2A H 0.1982 0.3957 0.4285 0.054 Uiso 1 1 calc R . . H2B H 0.1865 0.3440 0.5208 0.054 Uiso 1 1 calc R . . C3 C 0.0513(6) 0.2468(5) 0.4186(3) 0.0452(12) Uani 1 1 d . . . H3 H -0.0130 0.2996 0.3731 0.054 Uiso 1 1 calc R . . C4 C -0.0460(7) 0.1866(6) 0.4751(4) 0.0617(16) Uani 1 1 d . . . H4A H -0.1107 0.1219 0.4398 0.074 Uiso 1 1 calc R . . C5 C 0.0506(8) 0.1234(6) 0.5546(4) 0.0626(17) Uani 1 1 d . . . H5A H 0.1224 0.1833 0.5868 0.094 Uiso 1 1 calc R . . H5B H 0.1032 0.0532 0.5368 0.094 Uiso 1 1 calc R . . H5C H -0.0120 0.0931 0.5913 0.094 Uiso 1 1 calc R . . C6 C -0.1445(7) 0.2851(6) 0.4994(5) 0.0707(19) Uani 1 1 d . . . H6A H -0.2065 0.2473 0.5339 0.106 Uiso 1 1 calc R . . H6B H -0.2078 0.3214 0.4471 0.106 Uiso 1 1 calc R . . H6C H -0.0830 0.3504 0.5330 0.106 Uiso 1 1 calc R . . C7 C 0.2952(5) -0.0564(4) 0.3368(3) 0.0301(9) Uani 1 1 d . . . C8 C 0.3024(6) -0.2495(5) 0.2834(4) 0.0456(12) Uani 1 1 d . . . H8A H 0.2944 -0.3208 0.3210 0.055 Uiso 1 1 calc R . . H8B H 0.3480 -0.2784 0.2372 0.055 Uiso 1 1 calc R . . C9 C 0.1501(5) -0.1917(4) 0.2453(3) 0.0346(9) Uani 1 1 d . . . H9 H 0.0726 -0.2442 0.2615 0.041 Uiso 1 1 calc R . . C10 C 0.1093(5) -0.1732(5) 0.1472(3) 0.0390(10) Uani 1 1 d . . . H10 H 0.0147 -0.1250 0.1328 0.047 Uiso 1 1 calc R . . C11 C 0.2187(8) -0.0998(8) 0.1149(3) 0.074(2) Uani 1 1 d . . . H11A H 0.2256 -0.0159 0.1394 0.111 Uiso 1 1 calc R . . H11B H 0.1874 -0.0946 0.0520 0.111 Uiso 1 1 calc R . . H11C H 0.3157 -0.1404 0.1319 0.111 Uiso 1 1 calc R . . C12 C 0.0766(9) -0.2986(6) 0.1016(4) 0.0711(19) Uani 1 1 d . . . H12A H 0.0323 -0.2849 0.0402 0.107 Uiso 1 1 calc R . . H12B H 0.0076 -0.3458 0.1267 0.107 Uiso 1 1 calc R . . H12C H 0.1690 -0.3455 0.1085 0.107 Uiso 1 1 calc R . . C13 C 0.3645(4) 0.0498(5) 0.3940(2) 0.0286(7) Uani 1 1 d . . . C14 C 0.4396(6) -0.0043(5) 0.4843(3) 0.0429(12) Uani 1 1 d . . . H14A H 0.4904 0.0625 0.5216 0.064 Uiso 1 1 calc R . . H14B H 0.5115 -0.0682 0.4784 0.064 Uiso 1 1 calc R . . H14C H 0.3640 -0.0414 0.5097 0.064 Uiso 1 1 calc R . . C15 C 0.4872(5) 0.1132(4) 0.3581(3) 0.0321(9) Uani 1 1 d . . . H15A H 0.5286 0.1835 0.3963 0.038 Uiso 1 1 calc R . . H15B H 0.5680 0.0525 0.3607 0.038 Uiso 1 1 calc R . . C16 C 0.4378(5) 0.1616(4) 0.2669(3) 0.0367(10) Uani 1 1 d . . . H16A H 0.5221 0.2040 0.2516 0.044 Uiso 1 1 calc R . . H16B H 0.4084 0.0905 0.2272 0.044 Uiso 1 1 calc R . . C17 C 0.3739(5) 0.4413(4) 0.1587(2) 0.0298(9) Uani 1 1 d . . . C18 C 0.4972(5) 0.5122(4) 0.1604(3) 0.0349(10) Uani 1 1 d . . . H18 H 0.5659 0.5303 0.2134 0.042 Uiso 1 1 calc R . . C19 C 0.5199(5) 0.5570(5) 0.0829(3) 0.0365(9) Uani 1 1 d . . . H19 H 0.6046 0.6063 0.0835 0.044 Uiso 1 1 calc R . . C20 C 0.4218(4) 0.5310(5) 0.0061(2) 0.0332(9) Uani 1 1 d . . . C21 C 0.3003(6) 0.4553(6) 0.0063(3) 0.0470(12) Uani 1 1 d . . . H21 H 0.2337 0.4341 -0.0467 0.056 Uiso 1 1 calc R . . C22 C 0.2750(6) 0.4110(5) 0.0818(3) 0.0434(12) Uani 1 1 d . . . H22 H 0.1912 0.3604 0.0813 0.052 Uiso 1 1 calc R . . C23 C 0.4480(6) 0.5820(6) -0.0765(3) 0.0494(14) Uani 1 1 d . . . H23A H 0.4805 0.6687 -0.0678 0.074 Uiso 1 1 calc R . . H23B H 0.3560 0.5777 -0.1218 0.074 Uiso 1 1 calc R . . H23C H 0.5246 0.5326 -0.0934 0.074 Uiso 1 1 calc R . . C24 C -0.2136(5) -0.1117(4) 0.2737(3) 0.0343(9) Uani 1 1 d . . . C25 C -0.3244(7) -0.2129(7) 0.2450(4) 0.0685(19) Uani 1 1 d . . . H25A H -0.3328 -0.2313 0.1842 0.103 Uiso 1 1 calc R . . H25B H -0.4208 -0.1862 0.2528 0.103 Uiso 1 1 calc R . . H25C H -0.2923 -0.2878 0.2794 0.103 Uiso 1 1 calc R . . C26 C -0.0813(6) 0.2357(5) 0.1816(3) 0.0443(12) Uani 1 1 d . . . C27 C -0.1500(8) 0.3550(6) 0.1411(4) 0.0703(19) Uani 1 1 d . . . H27A H -0.2341 0.3770 0.1649 0.105 Uiso 1 1 calc R . . H27B H -0.1845 0.3439 0.0788 0.105 Uiso 1 1 calc R . . H27C H -0.0762 0.4218 0.1535 0.105 Uiso 1 1 calc R . . Cu1 Cu -0.00704(5) 0.04537(5) 0.28240(3) 0.03259(14) Uani 1 1 d . . . N1 N 0.1136(4) 0.1449(3) 0.3776(2) 0.0330(8) Uani 1 1 d . . . N2 N 0.1611(4) -0.0701(3) 0.2925(2) 0.0283(7) Uani 1 1 d . . . N4 N 0.3139(5) 0.2483(4) 0.2555(2) 0.0361(9) Uani 1 1 d D . . O1 O 0.3113(4) 0.2339(3) 0.46267(19) 0.0385(7) Uani 1 1 d . . . O2 O 0.3889(4) -0.1493(3) 0.3326(2) 0.0393(7) Uani 1 1 d . . . O4 O 0.2007(4) 0.4506(3) 0.2624(2) 0.0504(9) Uani 1 1 d . . . O5 O 0.4697(4) 0.4220(3) 0.32424(19) 0.0474(9) Uani 1 1 d . . . O6 O -0.1493(4) -0.0749(4) 0.2170(2) 0.0442(9) Uani 1 1 d . . . O7 O -0.1831(4) -0.0714(3) 0.3487(2) 0.0419(8) Uani 1 1 d . . . O8 O -0.1369(4) 0.1875(4) 0.2396(2) 0.0469(9) Uani 1 1 d . . . O9 O 0.0260(4) 0.1910(3) 0.1604(2) 0.0423(8) Uani 1 1 d . . . S1 S 0.33906(15) 0.39580(10) 0.25832(7) 0.0373(3) Uani 1 1 d . . . H4 H 0.220(3) 0.221(5) 0.228(3) 0.057(17) 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 0.039(3) 0.038(2) 0.0194(19) 0.0004(16) 0.0147(18) 0.0005(18) C2 0.065(3) 0.047(3) 0.031(2) -0.005(2) 0.027(2) 0.016(2) C3 0.043(3) 0.055(3) 0.042(3) 0.002(2) 0.021(2) 0.015(2) C4 0.072(4) 0.066(4) 0.059(4) -0.012(3) 0.040(3) -0.005(3) C5 0.081(4) 0.065(4) 0.060(4) 0.005(3) 0.051(4) 0.003(3) C6 0.065(4) 0.066(4) 0.091(5) -0.039(4) 0.039(4) -0.011(3) C7 0.030(2) 0.037(2) 0.0235(19) 0.0046(16) 0.0055(17) 0.0019(17) C8 0.052(3) 0.030(2) 0.047(3) -0.009(2) -0.003(2) 0.003(2) C9 0.037(2) 0.032(2) 0.032(2) 0.0007(17) 0.0015(19) -0.0049(18) C10 0.040(3) 0.048(3) 0.025(2) -0.0086(19) 0.0006(19) -0.005(2) C11 0.083(5) 0.113(6) 0.026(3) -0.011(3) 0.015(3) -0.037(4) C12 0.102(5) 0.046(3) 0.050(3) -0.012(3) -0.008(3) -0.005(3) C13 0.0268(17) 0.0361(19) 0.0215(16) 0.001(2) 0.0033(14) -0.002(2) C14 0.047(3) 0.053(3) 0.021(2) 0.0013(19) -0.007(2) 0.001(2) C15 0.031(2) 0.032(2) 0.033(2) -0.0129(17) 0.0070(19) -0.0019(16) C16 0.047(3) 0.036(2) 0.032(2) -0.0098(18) 0.019(2) -0.012(2) C17 0.043(2) 0.028(2) 0.0195(19) -0.0020(15) 0.0099(17) -0.0011(18) C18 0.038(2) 0.040(3) 0.026(2) 0.0000(16) 0.0068(18) -0.0028(17) C19 0.034(2) 0.046(3) 0.031(2) 0.007(2) 0.0087(16) -0.008(2) C20 0.033(2) 0.047(3) 0.0224(18) 0.0044(19) 0.0107(16) 0.005(2) C21 0.037(3) 0.079(4) 0.025(2) -0.002(2) 0.008(2) -0.009(2) C22 0.044(3) 0.060(3) 0.029(2) -0.006(2) 0.015(2) -0.016(2) C23 0.041(3) 0.081(4) 0.028(2) 0.011(2) 0.011(2) -0.001(2) C24 0.028(2) 0.043(2) 0.035(2) -0.0010(19) 0.0136(19) -0.0013(18) C25 0.066(4) 0.083(5) 0.064(4) -0.025(3) 0.029(3) -0.032(3) C26 0.041(3) 0.058(3) 0.031(2) 0.011(2) 0.003(2) 0.001(2) C27 0.075(4) 0.071(4) 0.064(4) 0.029(3) 0.014(3) 0.024(3) Cu1 0.0272(2) 0.0470(3) 0.0235(2) 0.0094(2) 0.00609(17) 0.0014(3) N1 0.036(2) 0.039(2) 0.0265(18) 0.0053(15) 0.0128(16) 0.0050(16) N2 0.0305(19) 0.0315(19) 0.0226(17) 0.0052(14) 0.0060(14) -0.0049(15) N4 0.045(2) 0.035(2) 0.0297(19) -0.0019(15) 0.0130(18) -0.0136(17) O1 0.0428(18) 0.0485(19) 0.0246(15) -0.0123(13) 0.0089(14) 0.0042(15) O2 0.0373(17) 0.0332(16) 0.0411(18) -0.0038(13) -0.0021(14) 0.0064(13) O4 0.076(3) 0.045(2) 0.0415(19) 0.0019(15) 0.0354(19) 0.0021(18) O5 0.081(3) 0.0395(19) 0.0217(15) -0.0059(13) 0.0130(16) -0.0214(17) O6 0.0361(19) 0.068(2) 0.0260(16) -0.0008(15) 0.0039(14) -0.0082(17) O7 0.056(2) 0.0418(18) 0.0341(17) -0.0009(14) 0.0220(15) -0.0116(16) O8 0.0352(19) 0.067(2) 0.0400(19) 0.0179(18) 0.0124(16) 0.0124(17) O9 0.0445(19) 0.052(2) 0.0308(16) 0.0020(15) 0.0100(15) -0.0006(16) S1 0.0606(8) 0.0343(6) 0.0215(5) -0.0032(4) 0.0187(5) -0.0097(5) _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 N1 1.269(6) . ? C1 O1 1.335(5) . ? C1 C13 1.504(6) . ? C2 O1 1.464(6) . ? C2 C3 1.517(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.469(6) . ? C3 C4 1.571(7) . ? C3 H3 1.0000 . ? C4 C6 1.514(8) . ? C4 C5 1.529(9) . ? C4 H4A 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.285(5) . ? C7 O2 1.339(5) . ? C7 C13 1.507(6) . ? C8 O2 1.457(6) . ? C8 C9 1.533(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.501(6) . ? C9 C10 1.539(6) . ? C9 H9 1.0000 . ? C10 C11 1.481(8) . ? C10 C12 1.529(7) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.558(6) . ? C13 C15 1.558(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.513(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.460(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.374(6) . ? C17 C22 1.385(6) . ? C17 S1 1.776(4) . ? C18 C19 1.396(6) . ? C18 H18 0.9500 . ? C19 C20 1.371(6) . ? C19 H19 0.9500 . ? C20 C21 1.396(7) . ? C20 C23 1.507(6) . ? C21 C22 1.375(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O7 1.245(5) . ? C24 O6 1.268(5) . ? C24 C25 1.494(7) . ? C24 Cu1 2.538(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 O9 1.231(6) . ? C26 O8 1.281(6) . ? C26 C27 1.508(8) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? Cu1 O6 1.962(4) . ? Cu1 O8 1.966(4) . ? Cu1 N1 1.974(4) . ? Cu1 N2 1.975(4) . ? N4 S1 1.603(4) . ? N4 H4 0.92(2) . ? O4 S1 1.434(4) . ? O5 S1 1.431(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 N1 C1 O1 117.1(4) . . ? N1 C1 C13 129.2(4) . . ? O1 C1 C13 113.5(4) . . ? O1 C2 C3 104.4(4) . . ? O1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? O1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? N1 C3 C2 101.9(4) . . ? N1 C3 C4 107.4(4) . . ? C2 C3 C4 119.6(4) . . ? N1 C3 H3 109.1 . . ? C2 C3 H3 109.1 . . ? C4 C3 H3 109.1 . . ? C6 C4 C5 111.5(5) . . ? C6 C4 C3 109.4(5) . . ? C5 C4 C3 111.1(5) . . ? C6 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 O2 116.4(4) . . ? N2 C7 C13 129.6(4) . . ? O2 C7 C13 114.1(3) . . ? O2 C8 C9 104.5(4) . . ? O2 C8 H8A 110.8 . . ? C9 C8 H8A 110.8 . . ? O2 C8 H8B 110.8 . . ? C9 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? N2 C9 C8 102.1(3) . . ? N2 C9 C10 111.9(4) . . ? C8 C9 C10 115.6(4) . . ? N2 C9 H9 109.0 . . ? C8 C9 H9 109.0 . . ? C10 C9 H9 109.0 . . ? C11 C10 C12 112.1(5) . . ? C11 C10 C9 114.1(4) . . ? C12 C10 C9 110.3(4) . . ? C11 C10 H10 106.6 . . ? C12 C10 H10 106.6 . . ? C9 C10 H10 106.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C13 C7 112.8(3) . . ? C1 C13 C14 106.7(3) . . ? C7 C13 C14 108.1(4) . . ? C1 C13 C15 110.8(4) . . ? C7 C13 C15 110.5(3) . . ? C14 C13 C15 107.7(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C13 115.5(4) . . ? C16 C15 H15A 108.4 . . ? C13 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C13 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? N4 C16 C15 112.6(3) . . ? N4 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? N4 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C22 121.3(4) . . ? C18 C17 S1 118.1(3) . . ? C22 C17 S1 120.5(3) . . ? C17 C18 C19 118.8(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.1(4) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 118.6(4) . . ? C19 C20 C23 120.0(4) . . ? C21 C20 C23 121.4(4) . . ? C22 C21 C20 121.3(4) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C17 118.8(4) . . ? C21 C22 H22 120.6 . . ? C17 C22 H22 120.6 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O7 C24 O6 123.3(4) . . ? O7 C24 C25 121.8(4) . . ? O6 C24 C25 114.8(4) . . ? O7 C24 Cu1 74.0(3) . . ? O6 C24 Cu1 49.3(2) . . ? C25 C24 Cu1 163.7(4) . . ? 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 . . ? O9 C26 O8 123.0(5) . . ? O9 C26 C27 120.1(5) . . ? O8 C26 C27 116.9(5) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 Cu1 O8 92.77(15) . . ? O6 Cu1 N1 162.32(14) . . ? O8 Cu1 N1 91.93(16) . . ? O6 Cu1 N2 92.77(16) . . ? O8 Cu1 N2 157.79(14) . . ? N1 Cu1 N2 89.27(14) . . ? O6 Cu1 C24 29.30(14) . . ? O8 Cu1 C24 95.98(16) . . ? N1 Cu1 C24 133.13(14) . . ? N2 Cu1 C24 99.34(14) . . ? C1 N1 C3 108.6(4) . . ? C1 N1 Cu1 128.5(3) . . ? C3 N1 Cu1 122.6(3) . . ? C7 N2 C9 108.4(4) . . ? C7 N2 Cu1 128.1(3) . . ? C9 N2 Cu1 123.4(3) . . ? C16 N4 S1 121.5(3) . . ? C16 N4 H4 119(4) . . ? S1 N4 H4 116(4) . . ? C1 O1 C2 105.1(3) . . ? C7 O2 C8 107.3(3) . . ? C24 O6 Cu1 101.4(3) . . ? C26 O8 Cu1 104.1(3) . . ? O5 S1 O4 119.8(2) . . ? O5 S1 N4 107.9(2) . . ? O4 S1 N4 106.3(2) . . ? O5 S1 C17 107.5(2) . . ? O4 S1 C17 107.0(2) . . ? N4 S1 C17 107.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N1 -16.5(4) . . . . ? O1 C2 C3 C4 101.6(5) . . . . ? N1 C3 C4 C6 -164.9(5) . . . . ? C2 C3 C4 C6 79.8(6) . . . . ? N1 C3 C4 C5 71.6(6) . . . . ? C2 C3 C4 C5 -43.7(7) . . . . ? O2 C8 C9 N2 -10.5(5) . . . . ? O2 C8 C9 C10 111.2(4) . . . . ? N2 C9 C10 C11 61.2(6) . . . . ? C8 C9 C10 C11 -55.1(6) . . . . ? N2 C9 C10 C12 -171.6(4) . . . . ? C8 C9 C10 C12 72.0(6) . . . . ? N1 C1 C13 C7 -0.2(6) . . . . ? O1 C1 C13 C7 175.6(3) . . . . ? N1 C1 C13 C14 -118.7(5) . . . . ? O1 C1 C13 C14 57.0(5) . . . . ? N1 C1 C13 C15 124.3(5) . . . . ? O1 C1 C13 C15 -59.9(4) . . . . ? N2 C7 C13 C1 7.9(6) . . . . ? O2 C7 C13 C1 -171.9(3) . . . . ? N2 C7 C13 C14 125.6(5) . . . . ? O2 C7 C13 C14 -54.1(5) . . . . ? N2 C7 C13 C15 -116.7(5) . . . . ? O2 C7 C13 C15 63.5(5) . . . . ? C1 C13 C15 C16 -68.9(4) . . . . ? C7 C13 C15 C16 56.9(5) . . . . ? C14 C13 C15 C16 174.7(4) . . . . ? C13 C15 C16 N4 55.7(5) . . . . ? C22 C17 C18 C19 1.9(7) . . . . ? S1 C17 C18 C19 -175.0(4) . . . . ? C17 C18 C19 C20 -0.2(7) . . . . ? C18 C19 C20 C21 -1.9(8) . . . . ? C18 C19 C20 C23 179.2(5) . . . . ? C19 C20 C21 C22 2.4(8) . . . . ? C23 C20 C21 C22 -178.7(5) . . . . ? C20 C21 C22 C17 -0.8(8) . . . . ? C18 C17 C22 C21 -1.3(8) . . . . ? S1 C17 C22 C21 175.4(4) . . . . ? O7 C24 Cu1 O6 -179.2(5) . . . . ? C25 C24 Cu1 O6 13.1(14) . . . . ? O7 C24 Cu1 O8 -94.2(3) . . . . ? O6 C24 Cu1 O8 85.0(3) . . . . ? C25 C24 Cu1 O8 98.1(15) . . . . ? O7 C24 Cu1 N1 4.1(4) . . . . ? O6 C24 Cu1 N1 -176.7(3) . . . . ? C25 C24 Cu1 N1 -163.6(14) . . . . ? O7 C24 Cu1 N2 101.9(3) . . . . ? O6 C24 Cu1 N2 -78.9(3) . . . . ? C25 C24 Cu1 N2 -65.8(15) . . . . ? O1 C1 N1 C3 -3.4(5) . . . . ? C13 C1 N1 C3 172.2(4) . . . . ? O1 C1 N1 Cu1 169.4(3) . . . . ? C13 C1 N1 Cu1 -15.0(7) . . . . ? C2 C3 N1 C1 12.6(5) . . . . ? C4 C3 N1 C1 -113.9(5) . . . . ? C2 C3 N1 Cu1 -160.7(3) . . . . ? C4 C3 N1 Cu1 72.8(5) . . . . ? O6 Cu1 N1 C1 114.2(6) . . . . ? O8 Cu1 N1 C1 -140.5(4) . . . . ? N2 Cu1 N1 C1 17.3(4) . . . . ? C24 Cu1 N1 C1 119.5(4) . . . . ? O6 Cu1 N1 C3 -73.9(6) . . . . ? O8 Cu1 N1 C3 31.4(3) . . . . ? N2 Cu1 N1 C3 -170.7(3) . . . . ? C24 Cu1 N1 C3 -68.6(4) . . . . ? O2 C7 N2 C9 -1.3(5) . . . . ? C13 C7 N2 C9 179.0(4) . . . . ? O2 C7 N2 Cu1 -180.0(3) . . . . ? C13 C7 N2 Cu1 0.3(6) . . . . ? C8 C9 N2 C7 7.5(5) . . . . ? C10 C9 N2 C7 -116.7(4) . . . . ? C8 C9 N2 Cu1 -173.7(3) . . . . ? C10 C9 N2 Cu1 62.1(5) . . . . ? O6 Cu1 N2 C7 -172.7(4) . . . . ? O8 Cu1 N2 C7 83.0(6) . . . . ? N1 Cu1 N2 C7 -10.3(4) . . . . ? C24 Cu1 N2 C7 -144.0(4) . . . . ? O6 Cu1 N2 C9 8.7(3) . . . . ? O8 Cu1 N2 C9 -95.6(5) . . . . ? N1 Cu1 N2 C9 171.1(3) . . . . ? C24 Cu1 N2 C9 37.4(3) . . . . ? C15 C16 N4 S1 97.6(4) . . . . ? N1 C1 O1 C2 -8.0(5) . . . . ? C13 C1 O1 C2 175.7(3) . . . . ? C3 C2 O1 C1 15.1(4) . . . . ? N2 C7 O2 C8 -6.1(5) . . . . ? C13 C7 O2 C8 173.7(4) . . . . ? C9 C8 O2 C7 10.3(5) . . . . ? O7 C24 O6 Cu1 0.9(5) . . . . ? C25 C24 O6 Cu1 -176.0(4) . . . . ? O8 Cu1 O6 C24 -97.3(3) . . . . ? N1 Cu1 O6 C24 7.9(7) . . . . ? N2 Cu1 O6 C24 104.2(3) . . . . ? O9 C26 O8 Cu1 2.9(6) . . . . ? C27 C26 O8 Cu1 -175.0(4) . . . . ? O6 Cu1 O8 C26 -102.4(3) . . . . ? N1 Cu1 O8 C26 94.7(4) . . . . ? N2 Cu1 O8 C26 1.9(7) . . . . ? C24 Cu1 O8 C26 -131.6(3) . . . . ? C16 N4 S1 O5 -38.9(4) . . . . ? C16 N4 S1 O4 -168.7(3) . . . . ? C16 N4 S1 C17 76.9(4) . . . . ? C18 C17 S1 O5 -12.3(4) . . . . ? C22 C17 S1 O5 170.8(4) . . . . ? C18 C17 S1 O4 117.6(4) . . . . ? C22 C17 S1 O4 -59.2(4) . . . . ? C18 C17 S1 N4 -128.4(4) . . . . ? C22 C17 S1 N4 54.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.471 _refine_diff_density_min -0.880 _refine_diff_density_rms 0.086 #===END data_ga_ms6a _database_code_depnum_ccdc_archive 'CCDC 283314' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H38 Cu N4 O6' _chemical_formula_weight 602.17 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.1940(10) _cell_length_b 16.122(2) _cell_length_c 19.152(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2838.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 0.819 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7913 _exptl_absorpt_correction_T_max 0.8870 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10824 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4819 _reflns_number_gt 3924 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'NONIUS Denzo' _computing_data_reduction 'NONIUS Denzo' _computing_structure_solution 'DIRDIF (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0346P)^2^+3.4111P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.015(18) _refine_ls_number_reflns 4819 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 C1 C 0.2112(5) 0.9404(3) 0.9017(2) 0.0149(10) Uani 1 1 d . . . C2 C 0.2611(5) 0.8955(3) 1.0098(2) 0.0177(11) Uani 1 1 d . . . H2A H 0.2766 0.9350 1.0473 0.021 Uiso 1 1 calc R . . H2B H 0.3043 0.8429 1.0228 0.021 Uiso 1 1 calc R . . C3 C 0.0980(5) 0.8854(3) 0.9942(2) 0.0155(10) Uani 1 1 d . . . H3 H 0.0418 0.9183 1.0277 0.019 Uiso 1 1 calc R . . C4 C 0.0428(5) 0.7957(3) 0.9951(2) 0.0187(11) Uani 1 1 d . . . H4 H -0.0599 0.7964 0.9814 0.022 Uiso 1 1 calc R . . C5 C 0.0517(6) 0.7622(3) 1.0696(3) 0.0285(13) Uani 1 1 d . . . H5A H 0.0149 0.7065 1.0708 0.043 Uiso 1 1 calc R . . H5B H -0.0054 0.7966 1.1000 0.043 Uiso 1 1 calc R . . H5C H 0.1512 0.7625 1.0849 0.043 Uiso 1 1 calc R . . C6 C 0.1239(5) 0.7401(3) 0.9438(2) 0.0227(12) Uani 1 1 d . . . H6A H 0.2244 0.7369 0.9570 0.034 Uiso 1 1 calc R . . H6B H 0.1162 0.7628 0.8977 0.034 Uiso 1 1 calc R . . H6C H 0.0820 0.6856 0.9446 0.034 Uiso 1 1 calc R . . C7 C 0.1332(5) 1.0089(3) 0.7907(2) 0.0154(11) Uani 1 1 d . . . C8 C 0.0411(5) 1.0779(3) 0.6983(2) 0.0221(11) Uani 1 1 d . . . H8A H 0.0457 1.0526 0.6524 0.027 Uiso 1 1 calc R . . H8B H 0.0276 1.1373 0.6929 0.027 Uiso 1 1 calc R . . C9 C -0.0834(5) 1.0396(3) 0.7423(2) 0.0166(11) Uani 1 1 d . . . H9 H -0.1369 1.0000 0.7132 0.020 Uiso 1 1 calc R . . C10 C -0.1915(6) 1.1006(3) 0.7745(2) 0.0222(12) Uani 1 1 d . . . H10 H -0.2517 1.0691 0.8074 0.027 Uiso 1 1 calc R . . C11 C -0.2931(6) 1.1350(3) 0.7184(3) 0.0295(13) Uani 1 1 d . . . H11A H -0.3646 1.1701 0.7398 0.044 Uiso 1 1 calc R . . H11B H -0.3408 1.0899 0.6950 0.044 Uiso 1 1 calc R . . H11C H -0.2377 1.1665 0.6852 0.044 Uiso 1 1 calc R . . C12 C -0.1183(6) 1.1695(3) 0.8156(3) 0.0296(13) Uani 1 1 d . . . H12A H -0.0615 1.2032 0.7846 0.044 Uiso 1 1 calc R . . H12B H -0.0561 1.1458 0.8506 0.044 Uiso 1 1 calc R . . H12C H -0.1912 1.2032 0.8378 0.044 Uiso 1 1 calc R . . C13 C 0.2559(5) 0.9679(3) 0.8287(2) 0.0150(11) Uani 1 1 d . . . C14 C 0.3911(5) 1.0243(3) 0.8336(2) 0.0175(10) Uani 1 1 d . . . H14A H 0.4708 0.9922 0.8529 0.021 Uiso 1 1 calc R . . H14B H 0.4187 1.0409 0.7868 0.021 Uiso 1 1 calc R . . C15 C 0.3725(5) 1.1007(3) 0.8769(2) 0.0165(10) Uani 1 1 d . . . C16 C 0.2172(6) 1.1968(3) 0.9244(3) 0.0231(12) Uani 1 1 d . . . H16 H 0.1226 1.2147 0.9326 0.028 Uiso 1 1 calc R . . C17 C 0.3280(6) 1.2447(3) 0.9489(3) 0.0257(13) Uani 1 1 d . . . H17 H 0.3094 1.2937 0.9730 0.031 Uiso 1 1 calc R . . C18 C 0.4700(6) 1.2182(3) 0.9367(3) 0.0276(13) Uani 1 1 d . . . H18 H 0.5486 1.2493 0.9524 0.033 Uiso 1 1 calc R . . C19 C 0.4921(6) 1.1447(3) 0.9007(2) 0.0228(12) Uani 1 1 d . . . H19 H 0.5858 1.1252 0.8927 0.027 Uiso 1 1 calc R . . C20 C 0.2931(5) 0.8866(3) 0.7880(2) 0.0185(11) Uani 1 1 d . . . H20A H 0.3759 0.8603 0.8103 0.022 Uiso 1 1 calc R . . H20B H 0.2113 0.8489 0.7917 0.022 Uiso 1 1 calc R . . C21 C 0.3278(6) 0.8994(3) 0.7118(3) 0.0206(12) Uani 1 1 d . . . C22 C 0.2450(6) 0.8990(3) 0.5984(3) 0.0261(13) Uani 1 1 d . . . H22 H 0.1696 0.8921 0.5666 0.031 Uiso 1 1 calc R . . C23 C 0.3820(7) 0.9190(3) 0.5733(2) 0.0287(13) Uani 1 1 d . . . H23 H 0.3978 0.9255 0.5256 0.034 Uiso 1 1 calc R . . C24 C 0.4935(6) 0.9290(3) 0.6199(2) 0.0263(11) Uani 1 1 d . . . H24 H 0.5865 0.9425 0.6044 0.032 Uiso 1 1 calc R . . C25 C 0.4661(6) 0.9188(3) 0.6903(2) 0.0218(12) Uani 1 1 d . . . H25 H 0.5405 0.9251 0.7228 0.026 Uiso 1 1 calc R . . C26 C -0.2186(5) 0.8177(3) 0.7985(2) 0.0197(11) Uani 1 1 d . . . C27 C -0.3131(6) 0.7640(3) 0.7526(3) 0.0285(13) Uani 1 1 d . . . H27A H -0.3024 0.7810 0.7049 0.043 Uiso 1 1 calc R . . H27B H -0.4129 0.7698 0.7665 0.043 Uiso 1 1 calc R . . H27C H -0.2840 0.7071 0.7574 0.043 Uiso 1 1 calc R . . C28 C -0.2455(5) 0.9964(3) 0.9790(2) 0.0170(11) Uani 1 1 d . . . C29 C -0.3552(5) 1.0012(3) 1.0387(2) 0.0262(13) Uani 1 1 d . . . H29A H -0.3539 1.0559 1.0584 0.039 Uiso 1 1 calc R . . H29B H -0.3298 0.9614 1.0740 0.039 Uiso 1 1 calc R . . H29C H -0.4507 0.9892 1.0213 0.039 Uiso 1 1 calc R . . Cu1 Cu -0.10260(6) 0.93125(4) 0.87155(3) 0.01576(15) Uani 1 1 d . . . N1 N 0.0841(4) 0.9231(2) 0.92382(17) 0.0129(8) Uani 1 1 d . . . N2 N -0.0020(4) 0.9931(2) 0.79666(19) 0.0147(9) Uani 1 1 d . . . N3 N 0.2348(4) 1.1257(2) 0.88950(19) 0.0200(10) Uani 1 1 d . . . N4 N 0.2162(5) 0.8893(3) 0.6668(2) 0.0254(10) Uani 1 1 d . . . O1 O 0.3225(3) 0.9259(2) 0.94475(15) 0.0180(7) Uani 1 1 d . . . O2 O 0.1732(3) 1.0601(2) 0.73837(15) 0.0172(7) Uani 1 1 d . . . O3 O -0.1071(4) 0.7900(2) 0.82580(17) 0.0279(8) Uani 1 1 d . . . O4 O -0.2601(4) 0.8939(2) 0.80791(16) 0.0192(8) Uani 1 1 d . . . O5 O -0.2277(3) 0.9234(2) 0.95337(16) 0.0211(8) Uani 1 1 d . . . O6 O -0.1825(4) 1.0591(2) 0.95850(18) 0.0293(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.016(3) 0.013(3) 0.015(2) -0.002(2) -0.004(2) -0.002(2) C2 0.021(3) 0.017(3) 0.015(2) 0.001(2) -0.003(2) 0.003(2) C3 0.013(2) 0.020(3) 0.013(2) -0.001(2) 0.000(2) 0.005(2) C4 0.018(3) 0.022(3) 0.016(3) 0.006(2) -0.002(2) 0.002(2) C5 0.036(3) 0.026(3) 0.024(3) 0.005(2) 0.001(2) -0.003(3) C6 0.017(3) 0.018(3) 0.033(3) 0.005(2) -0.007(2) 0.002(2) C7 0.020(3) 0.009(2) 0.017(2) -0.002(2) 0.002(2) -0.002(2) C8 0.021(3) 0.026(3) 0.020(2) 0.004(2) -0.003(2) 0.004(2) C9 0.022(3) 0.011(2) 0.017(2) 0.0053(19) -0.002(2) -0.001(2) C10 0.025(3) 0.019(3) 0.022(3) 0.004(2) 0.004(2) -0.001(2) C11 0.020(3) 0.034(3) 0.035(3) 0.010(3) 0.004(2) 0.007(3) C12 0.037(3) 0.021(3) 0.030(3) -0.002(2) 0.002(3) -0.004(3) C13 0.018(3) 0.013(2) 0.014(2) 0.003(2) -0.003(2) 0.005(2) C14 0.011(2) 0.020(3) 0.022(3) 0.004(2) 0.002(2) 0.002(2) C15 0.016(3) 0.020(3) 0.013(2) 0.004(2) 0.001(2) -0.0066(19) C16 0.021(3) 0.025(3) 0.023(3) -0.003(2) 0.001(2) 0.002(2) C17 0.041(4) 0.017(3) 0.019(3) 0.001(2) -0.001(2) -0.006(3) C18 0.035(4) 0.027(3) 0.021(3) -0.002(3) -0.006(3) -0.012(3) C19 0.021(3) 0.025(3) 0.022(3) 0.004(2) 0.005(2) 0.001(2) C20 0.020(3) 0.016(3) 0.020(3) 0.000(2) 0.001(2) 0.002(2) C21 0.034(3) 0.005(2) 0.023(3) -0.006(2) -0.002(2) 0.007(2) C22 0.033(3) 0.021(3) 0.024(3) 0.000(2) -0.004(3) 0.005(2) C23 0.053(4) 0.018(3) 0.015(2) -0.004(2) 0.007(3) 0.006(3) C24 0.038(3) 0.018(3) 0.024(3) -0.003(3) 0.004(2) 0.005(3) C25 0.030(3) 0.016(3) 0.020(3) 0.001(2) 0.002(2) -0.002(2) C26 0.014(3) 0.027(3) 0.018(3) -0.001(2) 0.006(2) -0.007(2) C27 0.032(3) 0.023(3) 0.031(3) -0.006(3) -0.009(3) 0.003(3) C28 0.006(2) 0.025(3) 0.020(3) 0.001(2) -0.005(2) -0.002(2) C29 0.024(3) 0.032(3) 0.023(3) -0.008(3) 0.009(2) 0.001(2) Cu1 0.0147(3) 0.0165(3) 0.0161(3) 0.0017(3) -0.0006(3) -0.0012(3) N1 0.015(2) 0.012(2) 0.0114(18) 0.0008(17) -0.0016(16) 0.004(2) N2 0.015(2) 0.015(2) 0.014(2) 0.0032(18) -0.0019(17) 0.0012(18) N3 0.025(3) 0.018(2) 0.017(2) -0.0041(18) 0.0029(18) 0.0018(19) N4 0.032(3) 0.020(2) 0.024(2) -0.006(2) -0.001(2) 0.002(2) O1 0.0153(17) 0.0224(19) 0.0164(16) 0.0016(17) -0.0029(13) 0.0013(17) O2 0.0173(17) 0.0178(19) 0.0166(16) 0.0058(16) 0.0010(13) -0.0051(16) O3 0.024(2) 0.0249(19) 0.035(2) -0.0076(16) -0.0135(19) 0.0050(18) O4 0.0203(19) 0.0170(19) 0.0202(18) 0.0036(15) -0.0032(15) -0.0022(15) O5 0.0187(18) 0.022(2) 0.0223(17) 0.0005(18) 0.0051(14) 0.0003(17) O6 0.029(2) 0.019(2) 0.039(2) 0.0031(19) 0.0126(17) -0.0007(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. ; 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 N1 1.274(6) . ? C1 O1 1.335(5) . ? C1 C13 1.523(6) . ? C2 O1 1.453(5) . ? C2 C3 1.538(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.483(5) . ? C3 C4 1.533(7) . ? C3 H3 0.9800 . ? C4 C6 1.523(7) . ? C4 C5 1.529(6) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N2 1.274(6) . ? C7 O2 1.349(5) . ? C7 C13 1.497(6) . ? C8 O2 1.465(5) . ? C8 C9 1.549(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.486(5) . ? C9 C10 1.528(6) . ? C9 H9 0.9800 . ? C10 C12 1.520(7) . ? C10 C11 1.527(7) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.544(7) . ? C13 C20 1.563(6) . ? C14 C15 1.493(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.350(6) . ? C15 C19 1.386(7) . ? C16 N3 1.337(6) . ? C16 C17 1.362(7) . ? C16 H16 0.9300 . ? C17 C18 1.394(8) . ? C17 H17 0.9300 . ? C18 C19 1.386(7) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.509(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N4 1.349(7) . ? C21 C25 1.373(7) . ? C22 N4 1.346(6) . ? C22 C23 1.386(8) . ? C22 H22 0.9300 . ? C23 C24 1.369(7) . ? C23 H23 0.9300 . ? C24 C25 1.381(6) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 O3 1.235(6) . ? C26 O4 1.298(6) . ? C26 C27 1.508(7) . ? C26 Cu1 2.538(5) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O6 1.230(6) . ? C28 O5 1.286(6) . ? C28 C29 1.527(6) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? Cu1 O5 1.948(3) . ? Cu1 N2 1.976(4) . ? Cu1 O4 1.986(3) . ? Cu1 N1 1.991(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 N1 C1 O1 117.4(4) . . ? N1 C1 C13 128.0(4) . . ? O1 C1 C13 114.3(4) . . ? O1 C2 C3 104.4(3) . . ? O1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? O1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? N1 C3 C4 111.6(4) . . ? N1 C3 C2 102.6(4) . . ? C4 C3 C2 114.9(4) . . ? N1 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C6 C4 C5 111.6(4) . . ? C6 C4 C3 112.7(4) . . ? C5 C4 C3 109.0(4) . . ? C6 C4 H4 107.8 . . ? C5 C4 H4 107.8 . . ? C3 C4 H4 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 O2 117.1(4) . . ? N2 C7 C13 127.1(4) . . ? O2 C7 C13 115.2(4) . . ? O2 C8 C9 104.5(3) . . ? O2 C8 H8A 110.9 . . ? C9 C8 H8A 110.9 . . ? O2 C8 H8B 110.9 . . ? C9 C8 H8B 110.9 . . ? H8A C8 H8B 108.9 . . ? N2 C9 C10 111.6(4) . . ? N2 C9 C8 102.1(4) . . ? C10 C9 C8 116.3(4) . . ? N2 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C8 C9 H9 108.8 . . ? C12 C10 C11 111.7(4) . . ? C12 C10 C9 113.1(4) . . ? C11 C10 C9 110.3(4) . . ? C12 C10 H10 107.1 . . ? C11 C10 H10 107.1 . . ? C9 C10 H10 107.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 C1 111.8(4) . . ? C7 C13 C14 112.1(4) . . ? C1 C13 C14 109.4(4) . . ? C7 C13 C20 107.0(4) . . ? C1 C13 C20 105.8(4) . . ? C14 C13 C20 110.4(4) . . ? C15 C14 C13 115.3(4) . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? C13 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? N3 C15 C19 122.1(4) . . ? N3 C15 C14 116.9(4) . . ? C19 C15 C14 120.9(4) . . ? N3 C16 C17 124.6(5) . . ? N3 C16 H16 117.7 . . ? C17 C16 H16 117.7 . . ? C16 C17 C18 117.9(5) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? C19 C18 C17 118.9(5) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C15 C19 C18 119.0(5) . . ? C15 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C21 C20 C13 114.5(4) . . ? C21 C20 H20A 108.6 . . ? C13 C20 H20A 108.6 . . ? C21 C20 H20B 108.6 . . ? C13 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? N4 C21 C25 122.7(5) . . ? N4 C21 C20 116.1(5) . . ? C25 C21 C20 121.1(5) . . ? N4 C22 C23 123.0(5) . . ? N4 C22 H22 118.5 . . ? C23 C22 H22 118.5 . . ? C24 C23 C22 118.8(5) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 119.0(5) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C21 C25 C24 119.3(5) . . ? C21 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? O3 C26 O4 121.8(4) . . ? O3 C26 C27 121.1(5) . . ? O4 C26 C27 117.0(4) . . ? O3 C26 Cu1 71.3(3) . . ? O4 C26 Cu1 50.6(2) . . ? C27 C26 Cu1 167.6(4) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 O5 124.8(4) . . ? O6 C28 C29 120.6(5) . . ? O5 C28 C29 114.6(4) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O5 Cu1 N2 153.24(16) . . ? O5 Cu1 O4 92.48(14) . . ? N2 Cu1 O4 92.80(15) . . ? O5 Cu1 N1 95.75(14) . . ? N2 Cu1 N1 89.72(15) . . ? O4 Cu1 N1 156.45(14) . . ? O5 Cu1 C26 98.51(15) . . ? N2 Cu1 C26 99.23(15) . . ? O4 Cu1 C26 30.32(15) . . ? N1 Cu1 C26 126.27(16) . . ? C1 N1 C3 108.2(4) . . ? C1 N1 Cu1 127.5(3) . . ? C3 N1 Cu1 123.9(3) . . ? C7 N2 C9 109.1(4) . . ? C7 N2 Cu1 128.5(3) . . ? C9 N2 Cu1 121.9(3) . . ? C16 N3 C15 117.4(4) . . ? C22 N4 C21 117.2(5) . . ? C1 O1 C2 106.9(3) . . ? C7 O2 C8 106.4(3) . . ? C26 O4 Cu1 99.1(3) . . ? C28 O5 Cu1 108.8(3) . . ? 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 C2 C3 N1 -7.6(4) . . . . ? O1 C2 C3 C4 113.6(4) . . . . ? N1 C3 C4 C6 58.8(5) . . . . ? C2 C3 C4 C6 -57.3(5) . . . . ? N1 C3 C4 C5 -176.7(4) . . . . ? C2 C3 C4 C5 67.1(5) . . . . ? O2 C8 C9 N2 -8.5(5) . . . . ? O2 C8 C9 C10 113.3(4) . . . . ? N2 C9 C10 C12 65.0(5) . . . . ? C8 C9 C10 C12 -51.7(5) . . . . ? N2 C9 C10 C11 -169.1(4) . . . . ? C8 C9 C10 C11 74.2(5) . . . . ? N2 C7 C13 C1 -31.9(6) . . . . ? O2 C7 C13 C1 157.3(4) . . . . ? N2 C7 C13 C14 -155.3(5) . . . . ? O2 C7 C13 C14 33.9(5) . . . . ? N2 C7 C13 C20 83.5(6) . . . . ? O2 C7 C13 C20 -87.2(5) . . . . ? N1 C1 C13 C7 25.0(7) . . . . ? O1 C1 C13 C7 -161.6(4) . . . . ? N1 C1 C13 C14 149.9(5) . . . . ? O1 C1 C13 C14 -36.7(5) . . . . ? N1 C1 C13 C20 -91.2(6) . . . . ? O1 C1 C13 C20 82.2(5) . . . . ? C7 C13 C14 C15 66.0(5) . . . . ? C1 C13 C14 C15 -58.7(5) . . . . ? C20 C13 C14 C15 -174.8(4) . . . . ? C13 C14 C15 N3 -19.1(6) . . . . ? C13 C14 C15 C19 162.9(4) . . . . ? N3 C16 C17 C18 0.1(8) . . . . ? C16 C17 C18 C19 -0.2(8) . . . . ? N3 C15 C19 C18 -2.2(7) . . . . ? C14 C15 C19 C18 175.7(4) . . . . ? C17 C18 C19 C15 1.2(8) . . . . ? C7 C13 C20 C21 55.4(5) . . . . ? C1 C13 C20 C21 174.9(4) . . . . ? C14 C13 C20 C21 -66.8(5) . . . . ? C13 C20 C21 N4 -94.9(5) . . . . ? C13 C20 C21 C25 86.0(6) . . . . ? N4 C22 C23 C24 0.2(8) . . . . ? C22 C23 C24 C25 0.1(8) . . . . ? N4 C21 C25 C24 0.2(8) . . . . ? C20 C21 C25 C24 179.2(5) . . . . ? C23 C24 C25 C21 -0.3(8) . . . . ? O3 C26 Cu1 O5 -100.7(3) . . . . ? O4 C26 Cu1 O5 80.3(3) . . . . ? C27 C26 Cu1 O5 75.5(16) . . . . ? O3 C26 Cu1 N2 99.4(3) . . . . ? O4 C26 Cu1 N2 -79.6(3) . . . . ? C27 C26 Cu1 N2 -84.4(16) . . . . ? O3 C26 Cu1 O4 179.0(4) . . . . ? C27 C26 Cu1 O4 -4.8(15) . . . . ? O3 C26 Cu1 N1 2.9(3) . . . . ? O4 C26 Cu1 N1 -176.1(2) . . . . ? C27 C26 Cu1 N1 179.1(15) . . . . ? O1 C1 N1 C3 -3.0(6) . . . . ? C13 C1 N1 C3 170.2(4) . . . . ? O1 C1 N1 Cu1 -176.4(3) . . . . ? C13 C1 N1 Cu1 -3.2(8) . . . . ? C4 C3 N1 C1 -116.9(5) . . . . ? C2 C3 N1 C1 6.6(5) . . . . ? C4 C3 N1 Cu1 56.8(5) . . . . ? C2 C3 N1 Cu1 -179.7(3) . . . . ? O5 Cu1 N1 C1 -165.0(4) . . . . ? N2 Cu1 N1 C1 -11.3(4) . . . . ? O4 Cu1 N1 C1 85.1(6) . . . . ? C26 Cu1 N1 C1 90.0(5) . . . . ? O5 Cu1 N1 C3 22.6(3) . . . . ? N2 Cu1 N1 C3 176.3(3) . . . . ? O4 Cu1 N1 C3 -87.3(4) . . . . ? C26 Cu1 N1 C3 -82.4(3) . . . . ? O2 C7 N2 C9 -1.4(6) . . . . ? C13 C7 N2 C9 -172.0(4) . . . . ? O2 C7 N2 Cu1 -173.0(3) . . . . ? C13 C7 N2 Cu1 16.3(7) . . . . ? C10 C9 N2 C7 -118.7(4) . . . . ? C8 C9 N2 C7 6.3(5) . . . . ? C10 C9 N2 Cu1 53.6(5) . . . . ? C8 C9 N2 Cu1 178.6(3) . . . . ? O5 Cu1 N2 C7 107.4(5) . . . . ? O4 Cu1 N2 C7 -151.4(4) . . . . ? N1 Cu1 N2 C7 5.2(4) . . . . ? C26 Cu1 N2 C7 -121.6(4) . . . . ? O5 Cu1 N2 C9 -63.3(5) . . . . ? O4 Cu1 N2 C9 37.8(3) . . . . ? N1 Cu1 N2 C9 -165.6(3) . . . . ? C26 Cu1 N2 C9 67.7(3) . . . . ? C17 C16 N3 C15 -1.0(7) . . . . ? C19 C15 N3 C16 2.0(7) . . . . ? C14 C15 N3 C16 -175.9(4) . . . . ? C23 C22 N4 C21 -0.3(7) . . . . ? C25 C21 N4 C22 0.0(7) . . . . ? C20 C21 N4 C22 -179.0(4) . . . . ? N1 C1 O1 C2 -2.3(6) . . . . ? C13 C1 O1 C2 -176.5(4) . . . . ? C3 C2 O1 C1 6.3(5) . . . . ? N2 C7 O2 C8 -4.6(6) . . . . ? C13 C7 O2 C8 167.1(4) . . . . ? C9 C8 O2 C7 8.1(5) . . . . ? O3 C26 O4 Cu1 -1.1(5) . . . . ? C27 C26 O4 Cu1 178.8(4) . . . . ? O5 Cu1 O4 C26 -102.7(3) . . . . ? N2 Cu1 O4 C26 103.6(3) . . . . ? N1 Cu1 O4 C26 7.9(5) . . . . ? O6 C28 O5 Cu1 -6.0(6) . . . . ? C29 C28 O5 Cu1 173.5(3) . . . . ? N2 Cu1 O5 C28 -14.2(5) . . . . ? O4 Cu1 O5 C28 -115.4(3) . . . . ? N1 Cu1 O5 C28 86.7(3) . . . . ? C26 Cu1 O5 C28 -145.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.382 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.085