# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Volker Bohmer' _publ_contact_author_address ; Fachbereich Chemie und Pharmazie,Abteilung Lehramt Chemie Johannes Gutenberg Universitat Mainz Duesbergweg 10-14 Mainz 55099 GERMANY ; _publ_contact_author_email VBOEHMER@MAIL.UNI-MAINZ.DE _publ_section_title ; Conformational Properties of Cyanomethoxy Calix[4]arenes ; loop_ _publ_author_name 'Volker Bohmer' 'Michael Bolte' 'Crenguta Danila' data_boeh13 _database_code_depnum_ccdc_archive 'CCDC 272778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H48 N4 O8' _chemical_formula_weight 784.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7073(14) _cell_length_b 10.5690(14) _cell_length_c 10.9986(15) _cell_angle_alpha 92.126(11) _cell_angle_beta 109.791(10) _cell_angle_gamma 101.734(11) _cell_volume 1032.7(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10490 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 25.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11250 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 25.65 _reflns_number_total 3800 _reflns_number_gt 2611 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _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 Rfactors 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^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3800 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.06546(19) 0.79661(15) 0.50162(18) 0.0286(4) Uani 1 1 d . . . H1A H -0.0457 0.7809 0.5935 0.034 Uiso 1 1 calc R . . H1B H -0.0894 0.8832 0.4915 0.034 Uiso 1 1 calc R . . C11 C 0.07516(18) 0.79697(15) 0.46982(18) 0.0271(4) Uani 1 1 d . . . C12 C 0.18681(19) 0.73701(15) 0.54286(18) 0.0274(4) Uani 1 1 d . . . C13 C 0.30764(18) 0.72606(15) 0.50505(18) 0.0289(4) Uani 1 1 d . . . C14 C 0.3221(2) 0.78615(17) 0.3984(2) 0.0330(4) Uani 1 1 d . . . H14 H 0.4054 0.7808 0.3732 0.040 Uiso 1 1 calc R . . C15 C 0.2183(2) 0.85410(16) 0.3270(2) 0.0334(4) Uani 1 1 d . . . C16 C 0.09454(19) 0.85544(16) 0.36311(18) 0.0299(4) Uani 1 1 d . . . H16 H 0.0202 0.8978 0.3133 0.036 Uiso 1 1 calc R . . C151 C 0.2334(2) 0.9223(2) 0.2097(2) 0.0428(5) Uani 1 1 d . . . C152 C 0.1024(4) 0.8564(3) 0.0861(3) 0.0685(7) Uani 1 1 d . . . H15A H 0.1060 0.7654 0.0708 0.103 Uiso 1 1 calc R . . H15B H 0.1104 0.9017 0.0118 0.103 Uiso 1 1 calc R . . H15C H 0.0069 0.8600 0.0967 0.103 Uiso 1 1 calc R . . C153 C 0.2239(3) 1.0645(2) 0.2299(3) 0.0605(7) Uani 1 1 d . . . H15D H 0.3070 1.1091 0.3082 0.091 Uiso 1 1 calc R . . H15E H 0.1279 1.0670 0.2399 0.091 Uiso 1 1 calc R . . H15F H 0.2307 1.1081 0.1543 0.091 Uiso 1 1 calc R . . C154 C 0.3834(4) 0.9223(4) 0.1925(4) 0.0969(13) Uani 1 1 d . . . H15G H 0.4664 0.9669 0.2709 0.145 Uiso 1 1 calc R . . H15H H 0.3885 0.9675 0.1174 0.145 Uiso 1 1 calc R . . H15I H 0.3913 0.8324 0.1781 0.145 Uiso 1 1 calc R . . O12 O 0.17128(13) 0.68050(11) 0.65177(12) 0.0299(3) Uani 1 1 d . . . C17 C 0.2683(2) 0.75270(17) 0.77164(19) 0.0351(4) Uani 1 1 d . . . H17A H 0.3735 0.7676 0.7749 0.042 Uiso 1 1 calc R . . H17B H 0.2599 0.7021 0.8438 0.042 Uiso 1 1 calc R . . C18 C 0.2310(2) 0.87902(18) 0.78900(19) 0.0346(4) Uani 1 1 d . . . N19 N 0.1995(2) 0.97622(17) 0.7995(2) 0.0500(5) Uani 1 1 d . . . C2 C 0.42374(19) 0.65221(16) 0.5774(2) 0.0313(4) Uani 1 1 d . . . H2A H 0.4964 0.7102 0.6550 0.038 Uiso 1 1 calc R . . H2B H 0.4798 0.6356 0.5205 0.038 Uiso 1 1 calc R . . C21 C 0.36925(18) 0.52333(16) 0.62231(18) 0.0280(4) Uani 1 1 d . . . C22 C 0.24501(18) 0.42681(15) 0.54298(17) 0.0262(4) Uani 1 1 d . . . C23 C 0.20007(18) 0.30662(15) 0.58530(18) 0.0267(4) Uani 1 1 d . . . C24 C 0.28180(19) 0.28444(16) 0.71065(19) 0.0300(4) Uani 1 1 d . . . H24 H 0.2540 0.2044 0.7424 0.036 Uiso 1 1 calc R . . C25 C 0.40285(19) 0.37925(17) 0.78788(18) 0.0307(4) Uani 1 1 d . . . C26 C 0.44810(19) 0.49800(17) 0.74581(19) 0.0302(4) Uani 1 1 d . . . H26 H 0.5327 0.5612 0.8017 0.036 Uiso 1 1 calc R . . N25 N 0.48781(18) 0.35563(15) 0.91994(17) 0.0390(4) Uani 1 1 d . . . O251 O 0.43021(19) 0.26686(15) 0.96829(16) 0.0576(5) Uani 1 1 d . . . O252 O 0.61366(16) 0.42572(14) 0.97640(15) 0.0485(4) Uani 1 1 d . . . O22 O 0.15663(13) 0.45232(11) 0.42353(12) 0.0297(3) Uani 1 1 d . . . C27 C 0.2101(2) 0.4375(2) 0.3195(2) 0.0407(5) Uani 1 1 d . . . H27A H 0.2156 0.3460 0.3046 0.049 Uiso 1 1 calc R . . H27B H 0.3122 0.4935 0.3417 0.049 Uiso 1 1 calc R . . C28 C 0.1051(3) 0.4750(3) 0.1994(2) 0.0560(6) Uani 1 1 d . . . H28 H 0.1264 0.4657 0.1219 0.067 Uiso 1 1 calc R . . C29 C -0.0135(2) 0.5194(2) 0.1915(2) 0.0547(6) Uani 1 1 d . . . H29A H -0.0392 0.5303 0.2666 0.066 Uiso 1 1 calc R . . H29B H -0.0740 0.5408 0.1106 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0287(8) 0.0251(8) 0.0318(10) 0.0044(7) 0.0088(8) 0.0085(7) C11 0.0258(8) 0.0219(7) 0.0302(10) 0.0021(7) 0.0065(7) 0.0038(6) C12 0.0282(8) 0.0219(7) 0.0286(10) 0.0048(7) 0.0071(7) 0.0026(6) C13 0.0246(8) 0.0243(8) 0.0347(11) 0.0065(7) 0.0069(7) 0.0042(6) C14 0.0288(9) 0.0338(9) 0.0389(12) 0.0098(8) 0.0142(8) 0.0078(7) C15 0.0348(10) 0.0304(8) 0.0352(11) 0.0085(8) 0.0119(8) 0.0078(7) C16 0.0305(9) 0.0262(8) 0.0308(11) 0.0064(7) 0.0064(8) 0.0085(7) C151 0.0453(11) 0.0461(11) 0.0449(13) 0.0207(10) 0.0215(10) 0.0154(9) C152 0.095(2) 0.0665(15) 0.0361(14) 0.0144(12) 0.0210(14) 0.0038(14) C153 0.0805(17) 0.0413(11) 0.0630(17) 0.0226(12) 0.0317(14) 0.0073(11) C154 0.088(2) 0.156(3) 0.106(3) 0.094(3) 0.075(2) 0.073(2) O12 0.0287(6) 0.0297(6) 0.0296(7) 0.0093(5) 0.0075(5) 0.0070(5) C17 0.0354(10) 0.0371(9) 0.0290(11) 0.0065(8) 0.0042(8) 0.0124(8) C18 0.0356(10) 0.0366(10) 0.0284(11) 0.0073(8) 0.0077(8) 0.0067(8) N19 0.0573(11) 0.0412(9) 0.0483(13) 0.0047(8) 0.0128(9) 0.0145(8) C2 0.0234(8) 0.0311(8) 0.0385(11) 0.0096(8) 0.0090(8) 0.0065(7) C21 0.0222(8) 0.0272(8) 0.0358(11) 0.0073(7) 0.0094(7) 0.0091(6) C22 0.0225(8) 0.0297(8) 0.0290(10) 0.0081(7) 0.0085(7) 0.0119(6) C23 0.0243(8) 0.0266(8) 0.0305(10) 0.0045(7) 0.0091(7) 0.0091(6) C24 0.0299(9) 0.0263(8) 0.0339(11) 0.0082(7) 0.0100(8) 0.0083(7) C25 0.0293(9) 0.0343(9) 0.0278(10) 0.0080(8) 0.0053(8) 0.0132(7) C26 0.0217(8) 0.0312(8) 0.0345(11) 0.0035(8) 0.0051(7) 0.0075(6) N25 0.0390(9) 0.0387(8) 0.0323(10) 0.0079(7) 0.0021(8) 0.0112(7) O251 0.0647(10) 0.0510(9) 0.0378(9) 0.0201(8) 0.0003(8) -0.0011(7) O252 0.0365(8) 0.0520(8) 0.0413(9) 0.0096(7) -0.0051(7) 0.0076(7) O22 0.0256(6) 0.0357(6) 0.0275(7) 0.0092(5) 0.0071(5) 0.0092(5) C27 0.0401(10) 0.0522(11) 0.0346(12) 0.0070(9) 0.0178(9) 0.0127(9) C28 0.0531(14) 0.0810(16) 0.0308(13) 0.0154(12) 0.0136(10) 0.0093(12) C29 0.0428(12) 0.0658(14) 0.0420(14) 0.0242(12) 0.0009(10) 0.0036(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C23 1.519(2) 2_566 ? C1 C11 1.519(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C11 C16 1.397(2) . ? C11 C12 1.396(2) . ? C12 C13 1.394(2) . ? C12 O12 1.398(2) . ? C13 C14 1.390(3) . ? C13 C2 1.519(2) . ? C14 C15 1.396(2) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 C151 1.536(3) . ? C16 H16 0.9500 . ? C151 C154 1.531(3) . ? C151 C152 1.532(4) . ? C151 C153 1.537(3) . ? C152 H15A 0.9800 . ? C152 H15B 0.9800 . ? C152 H15C 0.9800 . ? C153 H15D 0.9800 . ? C153 H15E 0.9800 . ? C153 H15F 0.9800 . ? C154 H15G 0.9800 . ? C154 H15H 0.9800 . ? C154 H15I 0.9800 . ? O12 C17 1.414(2) . ? C17 C18 1.474(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N19 1.143(2) . ? C2 C21 1.521(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C21 C26 1.382(3) . ? C21 C22 1.406(3) . ? C22 O22 1.375(2) . ? C22 C23 1.406(2) . ? C23 C24 1.394(3) . ? C23 C1 1.519(2) 2_566 ? C24 C25 1.374(3) . ? C24 H24 0.9500 . ? C25 C26 1.392(2) . ? C25 N25 1.467(2) . ? C26 H26 0.9500 . ? N25 O251 1.225(2) . ? N25 O252 1.229(2) . ? O22 C27 1.423(2) . ? C27 C28 1.494(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.306(3) . ? C28 H28 0.9500 . ? C29 H29A 0.9500 . ? C29 H29B 0.9500 . ? 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 C23 C1 C11 112.33(15) 2_566 . ? C23 C1 H1A 109.1 2_566 . ? C11 C1 H1A 109.1 . . ? C23 C1 H1B 109.1 2_566 . ? C11 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? C16 C11 C12 117.78(15) . . ? C16 C11 C1 120.32(14) . . ? C12 C11 C1 121.88(15) . . ? C13 C12 C11 121.41(15) . . ? C13 C12 O12 119.78(14) . . ? C11 C12 O12 118.70(15) . . ? C14 C13 C12 118.41(15) . . ? C14 C13 C2 119.40(16) . . ? C12 C13 C2 122.18(15) . . ? C13 C14 C15 122.15(17) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C16 C15 C14 117.43(16) . . ? C16 C15 C151 119.65(15) . . ? C14 C15 C151 122.89(16) . . ? C15 C16 C11 122.55(15) . . ? C15 C16 H16 118.7 . . ? C11 C16 H16 118.7 . . ? C154 C151 C152 110.1(2) . . ? C154 C151 C153 108.0(2) . . ? C152 C151 C153 107.83(19) . . ? C154 C151 C15 112.32(17) . . ? C152 C151 C15 109.55(17) . . ? C153 C151 C15 108.97(19) . . ? C151 C152 H15A 109.5 . . ? C151 C152 H15B 109.5 . . ? H15A C152 H15B 109.5 . . ? C151 C152 H15C 109.5 . . ? H15A C152 H15C 109.5 . . ? H15B C152 H15C 109.5 . . ? C151 C153 H15D 109.5 . . ? C151 C153 H15E 109.5 . . ? H15D C153 H15E 109.5 . . ? C151 C153 H15F 109.5 . . ? H15D C153 H15F 109.5 . . ? H15E C153 H15F 109.5 . . ? C151 C154 H15G 109.5 . . ? C151 C154 H15H 109.5 . . ? H15G C154 H15H 109.5 . . ? C151 C154 H15I 109.5 . . ? H15G C154 H15I 109.5 . . ? H15H C154 H15I 109.5 . . ? C12 O12 C17 113.88(13) . . ? O12 C17 C18 111.39(14) . . ? O12 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? O12 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? N19 C18 C17 178.3(2) . . ? C13 C2 C21 118.33(14) . . ? C13 C2 H2A 107.7 . . ? C21 C2 H2A 107.7 . . ? C13 C2 H2B 107.7 . . ? C21 C2 H2B 107.7 . . ? H2A C2 H2B 107.1 . . ? C26 C21 C22 118.21(15) . . ? C26 C21 C2 118.52(16) . . ? C22 C21 C2 123.24(16) . . ? O22 C22 C23 117.84(15) . . ? O22 C22 C21 119.86(14) . . ? C23 C22 C21 122.13(15) . . ? C24 C23 C22 118.17(16) . . ? C24 C23 C1 120.37(14) . 2_566 ? C22 C23 C1 121.46(15) . 2_566 ? C25 C24 C23 119.45(15) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 122.45(16) . . ? C24 C25 N25 119.19(15) . . ? C26 C25 N25 118.36(16) . . ? C21 C26 C25 119.58(17) . . ? C21 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? O251 N25 O252 123.27(16) . . ? O251 N25 C25 118.46(16) . . ? O252 N25 C25 118.27(15) . . ? C22 O22 C27 116.13(13) . . ? O22 C27 C28 108.99(16) . . ? O22 C27 H27A 109.9 . . ? C28 C27 H27A 109.9 . . ? O22 C27 H27B 109.9 . . ? C28 C27 H27B 109.9 . . ? H27A C27 H27B 108.3 . . ? C29 C28 C27 125.9(2) . . ? C29 C28 H28 117.1 . . ? C27 C28 H28 117.1 . . ? C28 C29 H29A 120.0 . . ? C28 C29 H29B 120.0 . . ? H29A C29 H29B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 C1 C11 C16 78.73(19) 2_566 . . . ? C23 C1 C11 C12 -99.63(19) 2_566 . . . ? C16 C11 C12 C13 -5.2(3) . . . . ? C1 C11 C12 C13 173.23(16) . . . . ? C16 C11 C12 O12 178.57(16) . . . . ? C1 C11 C12 O12 -3.0(2) . . . . ? C11 C12 C13 C14 5.4(3) . . . . ? O12 C12 C13 C14 -178.36(17) . . . . ? C11 C12 C13 C2 -175.24(17) . . . . ? O12 C12 C13 C2 1.0(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C2 C13 C14 C15 179.23(18) . . . . ? C13 C14 C15 C16 -2.6(3) . . . . ? C13 C14 C15 C151 179.4(2) . . . . ? C14 C15 C16 C11 2.9(3) . . . . ? C151 C15 C16 C11 -179.05(18) . . . . ? C12 C11 C16 C15 0.9(3) . . . . ? C1 C11 C16 C15 -177.50(17) . . . . ? C16 C15 C151 C154 174.4(2) . . . . ? C14 C15 C151 C154 -7.6(3) . . . . ? C16 C15 C151 C152 -62.9(3) . . . . ? C14 C15 C151 C152 115.1(2) . . . . ? C16 C15 C151 C153 54.8(3) . . . . ? C14 C15 C151 C153 -127.2(2) . . . . ? C13 C12 O12 C17 77.79(19) . . . . ? C11 C12 O12 C17 -105.90(17) . . . . ? C12 O12 C17 C18 65.76(19) . . . . ? O12 C17 C18 N19 -2(8) . . . . ? C14 C13 C2 C21 -139.07(19) . . . . ? C12 C13 C2 C21 41.6(3) . . . . ? C13 C2 C21 C26 -136.72(18) . . . . ? C13 C2 C21 C22 45.2(3) . . . . ? C26 C21 C22 O22 174.84(16) . . . . ? C2 C21 C22 O22 -7.1(2) . . . . ? C26 C21 C22 C23 -0.3(2) . . . . ? C2 C21 C22 C23 177.74(16) . . . . ? O22 C22 C23 C24 -174.70(15) . . . . ? C21 C22 C23 C24 0.5(2) . . . . ? O22 C22 C23 C1 4.7(2) . . . 2_566 ? C21 C22 C23 C1 179.95(15) . . . 2_566 ? C22 C23 C24 C25 -0.3(2) . . . . ? C1 C23 C24 C25 -179.76(16) 2_566 . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C23 C24 C25 N25 179.63(16) . . . . ? C22 C21 C26 C25 -0.1(2) . . . . ? C2 C21 C26 C25 -178.27(16) . . . . ? C24 C25 C26 C21 0.3(3) . . . . ? N25 C25 C26 C21 -179.39(16) . . . . ? C24 C25 N25 O251 -16.4(3) . . . . ? C26 C25 N25 O251 163.34(18) . . . . ? C24 C25 N25 O252 163.34(18) . . . . ? C26 C25 N25 O252 -16.9(3) . . . . ? C23 C22 O22 C27 -102.00(18) . . . . ? C21 C22 O22 C27 82.6(2) . . . . ? C22 O22 C27 C28 -177.31(16) . . . . ? O22 C27 C28 C29 2.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.65 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.225 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.036 data_boeh17 _database_code_depnum_ccdc_archive 'CCDC 272779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H43 Cl N4 O8.50' _chemical_formula_weight 763.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4637(8) _cell_length_b 18.3534(12) _cell_length_c 19.8397(14) _cell_angle_alpha 74.256(5) _cell_angle_beta 85.809(6) _cell_angle_gamma 83.824(5) _cell_volume 3990.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 35216 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9245 _exptl_absorpt_correction_T_max 0.9355 _exptl_absorpt_process_details 'MULABS (Spek, 1990; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32778 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.03 _reflns_number_total 14045 _reflns_number_gt 10482 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _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 Rfactors 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^)+(0.1679P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14045 _refine_ls_number_parameters 1016 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2260 _refine_ls_wR_factor_gt 0.2126 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3769(3) 0.73481(17) 0.25331(17) 0.0360(6) Uani 1 1 d . . . H1A H 0.3461 0.7742 0.2122 0.043 Uiso 1 1 calc R . . H1B H 0.3124 0.7032 0.2752 0.043 Uiso 1 1 calc R . . C11 C 0.4160(2) 0.77306(17) 0.30569(16) 0.0332(6) Uani 1 1 d . . . C12 C 0.4843(2) 0.83582(16) 0.28440(15) 0.0308(6) Uani 1 1 d . . . C13 C 0.5254(2) 0.86928(15) 0.33313(15) 0.0303(6) Uani 1 1 d . . . C14 C 0.4991(2) 0.83910(16) 0.40367(16) 0.0332(6) Uani 1 1 d . . . H14 H 0.5278 0.8599 0.4375 0.040 Uiso 1 1 calc R . . C15 C 0.4307(3) 0.77821(18) 0.42494(16) 0.0374(7) Uani 1 1 d . . . C16 C 0.3886(3) 0.74567(17) 0.37647(17) 0.0358(6) Uani 1 1 d . . . H16 H 0.3410 0.7045 0.3923 0.043 Uiso 1 1 calc R . . O12 O 0.51385(18) 0.86848(12) 0.21660(11) 0.0367(5) Uani 1 1 d . . . H12 H 0.4898 0.8439 0.1912 0.044 Uiso 1 1 calc R . . N15 N 0.4013(3) 0.74815(16) 0.49977(14) 0.0437(6) Uani 1 1 d . . . O151 O 0.3183(2) 0.70860(16) 0.51687(13) 0.0557(6) Uani 1 1 d . . . O152 O 0.4615(3) 0.76362(15) 0.54243(13) 0.0580(7) Uani 1 1 d . . . C2 C 0.5984(2) 0.93674(15) 0.30830(15) 0.0308(6) Uani 1 1 d . . . H2A H 0.5887 0.9672 0.3429 0.037 Uiso 1 1 calc R . . H2B H 0.5698 0.9695 0.2631 0.037 Uiso 1 1 calc R . . C21 C 0.7282(2) 0.91137(15) 0.29891(15) 0.0307(6) Uani 1 1 d . . . C22 C 0.7845(3) 0.91870(15) 0.23323(15) 0.0312(6) Uani 1 1 d . . . C23 C 0.9002(3) 0.88796(16) 0.22582(17) 0.0344(6) Uani 1 1 d . . . C24 C 0.9610(3) 0.85464(16) 0.28593(18) 0.0375(7) Uani 1 1 d . . . H24 H 1.0397 0.8336 0.2814 0.045 Uiso 1 1 calc R . . C25 C 0.9110(3) 0.85070(16) 0.35323(17) 0.0355(6) Uani 1 1 d . . . C26 C 0.7940(3) 0.87816(16) 0.35830(16) 0.0339(6) Uani 1 1 d . . . H26 H 0.7572 0.8744 0.4035 0.041 Uiso 1 1 calc R . . O22 O 0.72129(18) 0.95203(11) 0.17280(11) 0.0328(4) Uani 1 1 d . . . C28 C 0.7172(3) 1.03371(16) 0.14680(16) 0.0386(7) Uani 1 1 d . . . H28A H 0.7423 1.0555 0.1833 0.046 Uiso 1 1 calc R . . H28B H 0.6358 1.0550 0.1354 0.046 Uiso 1 1 calc R . . C29 C 0.7956(3) 1.05410(17) 0.08349(18) 0.0404(7) Uani 1 1 d . . . N29 N 0.8561(3) 1.06576(16) 0.03418(17) 0.0522(7) Uani 1 1 d . . . C27 C 0.9846(3) 0.81529(17) 0.41871(18) 0.0421(7) Uani 1 1 d . . . C271 C 0.9144(3) 0.8201(2) 0.48653(19) 0.0525(9) Uani 1 1 d . . . H27A H 0.8440 0.7928 0.4912 0.079 Uiso 1 1 calc R . . H27B H 0.8911 0.8735 0.4849 0.079 Uiso 1 1 calc R . . H27C H 0.9631 0.7970 0.5268 0.079 Uiso 1 1 calc R . . C272 C 1.0238(3) 0.73115(19) 0.4233(2) 0.0546(9) Uani 1 1 d . . . H27D H 1.0692 0.7274 0.3804 0.082 Uiso 1 1 calc R . . H27E H 0.9544 0.7028 0.4287 0.082 Uiso 1 1 calc R . . H27F H 1.0727 0.7097 0.4638 0.082 Uiso 1 1 calc R . . C273 C 1.0935(3) 0.85828(19) 0.4131(2) 0.0488(8) Uani 1 1 d . . . H27G H 1.1400 0.8557 0.3702 0.073 Uiso 1 1 calc R . . H27H H 1.1411 0.8351 0.4538 0.073 Uiso 1 1 calc R . . H27I H 1.0693 0.9115 0.4116 0.073 Uiso 1 1 calc R . . C3 C 0.9565(3) 0.88679(17) 0.15427(18) 0.0384(7) Uani 1 1 d . . . H3A H 1.0400 0.8964 0.1530 0.046 Uiso 1 1 calc R . . H3B H 0.9170 0.9283 0.1179 0.046 Uiso 1 1 calc R . . C31 C 0.9488(3) 0.81117(17) 0.13712(16) 0.0360(6) Uani 1 1 d . . . C32 C 0.8436(3) 0.79105(17) 0.11792(16) 0.0351(6) Uani 1 1 d . . . C33 C 0.8370(3) 0.72071(17) 0.10274(16) 0.0349(6) Uani 1 1 d . . . C34 C 0.9379(3) 0.67186(17) 0.10567(17) 0.0378(7) Uani 1 1 d . . . H34 H 0.9361 0.6243 0.0956 0.045 Uiso 1 1 calc R . . C35 C 1.0416(3) 0.69261(17) 0.12338(17) 0.0373(7) Uani 1 1 d . . . C36 C 1.0481(3) 0.76155(17) 0.13924(17) 0.0380(7) Uani 1 1 d . . . H36 H 1.1206 0.7741 0.1514 0.046 Uiso 1 1 calc R . . O32 O 0.74216(18) 0.83720(12) 0.11099(12) 0.0391(5) Uani 1 1 d . . . H32 H 0.7484 0.8734 0.1285 0.047 Uiso 1 1 calc R . . N35 N 1.1492(2) 0.64166(15) 0.12522(17) 0.0452(7) Uani 1 1 d . . . O351 O 1.1437(2) 0.58104(13) 0.10960(15) 0.0500(6) Uani 1 1 d . . . O352 O 1.2404(2) 0.66120(16) 0.1403(2) 0.0699(9) Uani 1 1 d . . . C4 C 0.7210(3) 0.70063(17) 0.08361(17) 0.0378(7) Uani 1 1 d . . . H4A H 0.7366 0.6621 0.0567 0.045 Uiso 1 1 calc R . . H4B H 0.6798 0.7465 0.0531 0.045 Uiso 1 1 calc R . . C41 C 0.6420(3) 0.66977(17) 0.14787(17) 0.0358(6) Uani 1 1 d . . . C42 C 0.5421(3) 0.71135(16) 0.16666(16) 0.0327(6) Uani 1 1 d . . . C43 C 0.4768(2) 0.68507(16) 0.22894(16) 0.0338(6) Uani 1 1 d . . . C44 C 0.5095(3) 0.61196(17) 0.27044(17) 0.0387(7) Uani 1 1 d . . . H44 H 0.4660 0.5931 0.3131 0.046 Uiso 1 1 calc R . . C45 C 0.6034(3) 0.56592(17) 0.25154(18) 0.0419(7) Uani 1 1 d . A . C46 C 0.6705(3) 0.59703(17) 0.19094(18) 0.0400(7) Uani 1 1 d . . . H46 H 0.7379 0.5676 0.1786 0.048 Uiso 1 1 calc R . . O42 O 0.50758(18) 0.78388(11) 0.12381(11) 0.0345(4) Uani 1 1 d . . . C48 C 0.4478(3) 0.78397(18) 0.06314(16) 0.0385(7) Uani 1 1 d . . . H48A H 0.3620 0.7844 0.0737 0.046 Uiso 1 1 calc R . . H48B H 0.4751 0.7382 0.0470 0.046 Uiso 1 1 calc R . . C49 C 0.4755(3) 0.8535(2) 0.00888(19) 0.0463(8) Uani 1 1 d . . . N49 N 0.4988(3) 0.9076(2) -0.03312(19) 0.0674(10) Uani 1 1 d . . . C47 C 0.6323(3) 0.48341(18) 0.2952(2) 0.0516(9) Uani 1 1 d . . . C471 C 0.6893(11) 0.4847(4) 0.3618(6) 0.078(3) Uani 0.552(8) 1 d P A 1 H47A H 0.7561 0.5158 0.3495 0.118 Uiso 0.552(8) 1 calc PR A 1 H47B H 0.7169 0.4328 0.3872 0.118 Uiso 0.552(8) 1 calc PR A 1 H47C H 0.6317 0.5065 0.3916 0.118 Uiso 0.552(8) 1 calc PR A 1 C472 C 0.5326(6) 0.4392(3) 0.3056(4) 0.054(2) Uani 0.552(8) 1 d P A 1 H47D H 0.5028 0.4413 0.2600 0.081 Uiso 0.552(8) 1 calc PR A 1 H47E H 0.4707 0.4600 0.3337 0.081 Uiso 0.552(8) 1 calc PR A 1 H47F H 0.5566 0.3863 0.3300 0.081 Uiso 0.552(8) 1 calc PR A 1 C473 C 0.7346(8) 0.4400(4) 0.2546(6) 0.081(3) Uani 0.552(8) 1 d P A 1 H47G H 0.8053 0.4675 0.2466 0.122 Uiso 0.552(8) 1 calc PR A 1 H47H H 0.7068 0.4387 0.2094 0.122 Uiso 0.552(8) 1 calc PR A 1 H47I H 0.7532 0.3880 0.2833 0.122 Uiso 0.552(8) 1 calc PR A 1 C474 C 0.5445(10) 0.4633(5) 0.3652(6) 0.071(3) Uani 0.448(8) 1 d P A 2 H47J H 0.4628 0.4727 0.3513 0.106 Uiso 0.448(8) 1 calc PR A 2 H47K H 0.5574 0.4956 0.3956 0.106 Uiso 0.448(8) 1 calc PR A 2 H47L H 0.5608 0.4098 0.3906 0.106 Uiso 0.448(8) 1 calc PR A 2 C475 C 0.5990(9) 0.4311(5) 0.2521(5) 0.062(3) Uani 0.448(8) 1 d P A 2 H47M H 0.5168 0.4442 0.2395 0.092 Uiso 0.448(8) 1 calc PR A 2 H47N H 0.6094 0.3780 0.2799 0.092 Uiso 0.448(8) 1 calc PR A 2 H47O H 0.6497 0.4378 0.2093 0.092 Uiso 0.448(8) 1 calc PR A 2 C476 C 0.7523(9) 0.4678(6) 0.3180(8) 0.070(3) Uani 0.448(8) 1 d P A 2 H47P H 0.7650 0.4148 0.3457 0.105 Uiso 0.448(8) 1 calc PR A 2 H47Q H 0.7658 0.5016 0.3468 0.105 Uiso 0.448(8) 1 calc PR A 2 H47R H 0.8071 0.4766 0.2769 0.105 Uiso 0.448(8) 1 calc PR A 2 C5 C 0.2705(3) 0.00818(16) 0.24495(16) 0.0334(6) Uani 1 1 d . . . H5A H 0.2574 -0.0459 0.2661 0.040 Uiso 1 1 calc R . . H5B H 0.3238 0.0113 0.2029 0.040 Uiso 1 1 calc R . . C51 C 0.3260(2) 0.03907(16) 0.29715(16) 0.0308(6) Uani 1 1 d . . . C52 C 0.3790(2) 0.10859(16) 0.27242(15) 0.0324(6) Uani 1 1 d . . . C53 C 0.4201(2) 0.14422(16) 0.31991(16) 0.0328(6) Uani 1 1 d . . . C54 C 0.4123(2) 0.10880(16) 0.39070(16) 0.0334(6) Uani 1 1 d . . . H54 H 0.4397 0.1316 0.4235 0.040 Uiso 1 1 calc R . . C55 C 0.3636(2) 0.03887(16) 0.41401(16) 0.0325(6) Uani 1 1 d . . . C56 C 0.3208(2) 0.00479(16) 0.36773(15) 0.0313(6) Uani 1 1 d . . . H56 H 0.2878 -0.0424 0.3850 0.038 Uiso 1 1 calc R . . O52 O 0.3859(2) 0.13719(12) 0.20250(11) 0.0383(5) Uani 1 1 d . . . H52 H 0.4096 0.1808 0.1927 0.046 Uiso 1 1 calc R . . N55 N 0.3598(2) 0.00075(15) 0.48817(13) 0.0349(5) Uani 1 1 d . . . O551 O 0.3376(2) -0.06659(13) 0.50651(11) 0.0410(5) Uani 1 1 d . . . O552 O 0.3796(2) 0.03619(13) 0.52995(12) 0.0431(5) Uani 1 1 d . . . C6 C 0.4744(3) 0.21962(16) 0.29438(17) 0.0356(6) Uani 1 1 d . . . H6A H 0.5324 0.2169 0.2554 0.043 Uiso 1 1 calc R . . H6B H 0.5169 0.2278 0.3330 0.043 Uiso 1 1 calc R . . C61 C 0.3839(2) 0.28713(16) 0.26928(16) 0.0344(6) Uani 1 1 d . . . C62 C 0.3623(2) 0.31738(16) 0.19877(16) 0.0324(6) Uani 1 1 d . . . C63 C 0.2742(2) 0.37600(16) 0.17533(17) 0.0337(6) Uani 1 1 d . . . C64 C 0.2124(3) 0.40644(17) 0.22593(17) 0.0361(6) Uani 1 1 d . . . H64 H 0.1527 0.4467 0.2114 0.043 Uiso 1 1 calc R . . C65 C 0.2344(3) 0.38038(18) 0.29706(18) 0.0393(7) Uani 1 1 d . . . C66 C 0.3190(3) 0.31948(18) 0.31780(17) 0.0381(7) Uani 1 1 d . . . H66 H 0.3329 0.2994 0.3662 0.046 Uiso 1 1 calc R . . O62 O 0.42796(17) 0.28573(11) 0.14962(11) 0.0353(5) Uani 1 1 d . . . C68 C 0.5333(2) 0.32192(17) 0.12271(18) 0.0362(6) Uani 1 1 d . . . H68A H 0.5661 0.3406 0.1590 0.043 Uiso 1 1 calc R . . H68B H 0.5165 0.3656 0.0816 0.043 Uiso 1 1 calc R . . C69 C 0.6158(3) 0.26413(18) 0.10267(18) 0.0410(7) Uani 1 1 d . . . N69 N 0.6791(3) 0.21740(18) 0.0883(2) 0.0589(9) Uani 1 1 d . . . C67 C 0.1644(3) 0.4192(2) 0.3494(2) 0.0512(8) Uani 1 1 d . . . C671 C 0.1694(4) 0.5062(2) 0.3236(2) 0.0681(12) Uani 1 1 d . . . H67A H 0.1246 0.5304 0.3569 0.102 Uiso 1 1 calc R . . H67B H 0.1355 0.5252 0.2775 0.102 Uiso 1 1 calc R . . H67C H 0.2513 0.5180 0.3200 0.102 Uiso 1 1 calc R . . C672 C 0.2128(4) 0.3925(2) 0.4226(2) 0.0578(9) Uani 1 1 d . . . H67D H 0.1657 0.4184 0.4539 0.087 Uiso 1 1 calc R . . H67E H 0.2946 0.4044 0.4203 0.087 Uiso 1 1 calc R . . H67F H 0.2094 0.3374 0.4406 0.087 Uiso 1 1 calc R . . C673 C 0.0370(4) 0.3991(4) 0.3543(3) 0.0882(17) Uani 1 1 d . . . H67G H -0.0093 0.4232 0.3873 0.132 Uiso 1 1 calc R . . H67H H 0.0352 0.3438 0.3708 0.132 Uiso 1 1 calc R . . H67I H 0.0037 0.4175 0.3080 0.132 Uiso 1 1 calc R . . C7 C 0.2442(2) 0.40418(17) 0.09913(17) 0.0352(6) Uani 1 1 d . . . H7A H 0.3072 0.3846 0.0701 0.042 Uiso 1 1 calc R . . H7B H 0.2403 0.4604 0.0846 0.042 Uiso 1 1 calc R . . C71 C 0.1280(2) 0.37915(16) 0.08615(15) 0.0321(6) Uani 1 1 d . . . C72 C 0.1225(2) 0.30427(16) 0.08037(15) 0.0324(6) Uani 1 1 d . . . C73 C 0.0158(3) 0.27880(16) 0.06959(15) 0.0324(6) Uani 1 1 d . . . C74 C -0.0846(3) 0.32813(16) 0.06431(15) 0.0330(6) Uani 1 1 d . . . H74 H -0.1574 0.3123 0.0564 0.040 Uiso 1 1 calc R . . C75 C -0.0789(2) 0.40145(16) 0.07065(15) 0.0322(6) Uani 1 1 d . . . C76 C 0.0260(2) 0.42709(16) 0.08127(16) 0.0331(6) Uani 1 1 d . . . H76 H 0.0275 0.4774 0.0851 0.040 Uiso 1 1 calc R . . O72 O 0.22395(17) 0.25871(11) 0.08587(11) 0.0355(5) Uani 1 1 d . . . H72 H 0.2112 0.2160 0.0816 0.043 Uiso 1 1 calc R . . N75 N -0.1861(2) 0.45185(14) 0.06660(14) 0.0356(5) Uani 1 1 d . . . O751 O -0.18133(19) 0.51768(12) 0.06990(13) 0.0441(5) Uani 1 1 d . . . O752 O -0.28013(19) 0.42736(13) 0.06070(14) 0.0477(6) Uani 1 1 d . . . C8 C 0.0100(3) 0.19700(16) 0.06731(16) 0.0363(6) Uani 1 1 d . . . H8A H -0.0676 0.1913 0.0515 0.044 Uiso 1 1 calc R . . H8B H 0.0711 0.1840 0.0335 0.044 Uiso 1 1 calc R . . C81 C 0.0292(3) 0.14351(16) 0.13956(15) 0.0325(6) Uani 1 1 d . . . C82 C 0.1316(2) 0.09498(15) 0.15611(15) 0.0311(6) Uani 1 1 d . . . C83 C 0.1541(2) 0.05397(15) 0.22411(15) 0.0311(6) Uani 1 1 d . . . C84 C 0.0690(3) 0.06191(16) 0.27679(16) 0.0331(6) Uani 1 1 d . . . H84 H 0.0820 0.0332 0.3237 0.040 Uiso 1 1 calc R . . C85 C -0.0332(2) 0.11006(16) 0.26305(16) 0.0323(6) Uani 1 1 d . . . C86 C -0.0520(2) 0.14935(16) 0.19424(16) 0.0343(6) Uani 1 1 d . . . H86 H -0.1227 0.1815 0.1837 0.041 Uiso 1 1 calc R . . O82 O 0.21987(18) 0.09568(11) 0.10271(10) 0.0347(4) Uani 1 1 d . . . C88 C 0.2094(3) 0.04573(17) 0.06018(16) 0.0369(6) Uani 1 1 d . . . H88A H 0.2598 0.0607 0.0169 0.044 Uiso 1 1 calc R . . H88B H 0.1271 0.0505 0.0464 0.044 Uiso 1 1 calc R . . C89 C 0.2437(3) -0.03391(19) 0.09697(17) 0.0387(7) Uani 1 1 d . . . N89 N 0.2698(3) -0.09591(16) 0.12663(16) 0.0471(7) Uani 1 1 d . . . C87 C -0.1185(3) 0.12513(17) 0.32257(16) 0.0361(6) Uani 1 1 d . . . C871 C -0.1171(4) 0.2082(2) 0.3234(2) 0.0621(10) Uani 1 1 d . . . H87A H -0.1390 0.2416 0.2777 0.093 Uiso 1 1 calc R . . H87B H -0.0380 0.2172 0.3332 0.093 Uiso 1 1 calc R . . H87C H -0.1732 0.2191 0.3599 0.093 Uiso 1 1 calc R . . C872 C -0.0839(3) 0.0747(2) 0.39484(18) 0.0496(8) Uani 1 1 d . . . H87D H -0.0045 0.0837 0.4039 0.074 Uiso 1 1 calc R . . H87E H -0.0855 0.0211 0.3958 0.074 Uiso 1 1 calc R . . H87F H -0.1395 0.0869 0.4310 0.074 Uiso 1 1 calc R . . C873 C -0.2425(3) 0.10874(19) 0.31110(17) 0.0393(7) Uani 1 1 d . . . H87G H -0.2675 0.1402 0.2653 0.059 Uiso 1 1 calc R . . H87H H -0.2967 0.1205 0.3480 0.059 Uiso 1 1 calc R . . H87I H -0.2427 0.0549 0.3127 0.059 Uiso 1 1 calc R . . O1M O 0.5483(2) 0.58686(18) 0.03400(16) 0.0663(7) Uani 1 1 d . . . H1M H 0.6133 0.5701 0.0519 0.080 Uiso 1 1 calc R . . C1M C 0.4585(3) 0.5546(2) 0.0794(2) 0.0595(10) Uani 1 1 d . . . H1MA H 0.4539 0.5025 0.0764 0.089 Uiso 1 1 calc R . . H1MB H 0.3838 0.5847 0.0663 0.089 Uiso 1 1 calc R . . H1MC H 0.4745 0.5536 0.1275 0.089 Uiso 1 1 calc R . . C1L C 0.7646(3) 0.70066(18) 0.30752(19) 0.0445(8) Uani 1 1 d . . . H1L1 H 0.7781 0.7552 0.2944 0.053 Uiso 1 1 calc R . . H1L2 H 0.7064 0.6934 0.2760 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.89820(8) 0.64617(5) 0.29620(5) 0.0532(2) Uani 1 1 d . . . Cl2 Cl 0.70801(9) 0.67436(6) 0.39467(5) 0.0572(3) 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 0.0319(15) 0.0355(15) 0.0419(17) -0.0116(13) 0.0021(12) -0.0081(12) C11 0.0272(13) 0.0332(14) 0.0397(16) -0.0110(13) -0.0020(11) -0.0014(11) C12 0.0282(13) 0.0306(14) 0.0330(15) -0.0094(12) 0.0003(11) 0.0015(11) C13 0.0258(13) 0.0265(13) 0.0382(15) -0.0098(12) -0.0013(11) 0.0020(11) C14 0.0328(14) 0.0301(14) 0.0351(15) -0.0072(12) -0.0042(11) 0.0018(11) C15 0.0373(16) 0.0368(16) 0.0357(16) -0.0056(13) -0.0038(12) -0.0016(13) C16 0.0324(14) 0.0296(14) 0.0428(17) -0.0047(13) -0.0020(12) -0.0033(12) O12 0.0405(11) 0.0380(11) 0.0348(11) -0.0138(9) 0.0043(8) -0.0111(9) N15 0.0510(16) 0.0420(15) 0.0362(14) -0.0043(12) -0.0048(12) -0.0096(13) O151 0.0611(16) 0.0600(16) 0.0403(13) -0.0004(12) 0.0012(11) -0.0165(13) O152 0.0852(19) 0.0515(14) 0.0383(13) -0.0083(11) -0.0052(12) -0.0186(14) C2 0.0333(14) 0.0257(13) 0.0338(15) -0.0097(12) 0.0012(11) -0.0011(11) C21 0.0338(14) 0.0213(12) 0.0379(15) -0.0096(11) -0.0004(11) -0.0032(11) C22 0.0357(15) 0.0206(12) 0.0374(15) -0.0070(11) -0.0021(11) -0.0046(11) C23 0.0363(15) 0.0229(13) 0.0452(17) -0.0112(12) 0.0077(12) -0.0090(11) C24 0.0301(14) 0.0257(14) 0.057(2) -0.0121(14) -0.0024(13) -0.0035(11) C25 0.0334(15) 0.0267(14) 0.0465(18) -0.0073(13) -0.0042(12) -0.0085(12) C26 0.0370(15) 0.0246(13) 0.0396(16) -0.0068(12) -0.0005(12) -0.0055(11) O22 0.0404(11) 0.0214(9) 0.0356(11) -0.0066(8) 0.0008(8) -0.0026(8) C28 0.0562(19) 0.0211(13) 0.0369(16) -0.0064(12) -0.0016(13) 0.0005(13) C29 0.060(2) 0.0234(14) 0.0399(18) -0.0099(13) -0.0014(15) -0.0076(13) N29 0.076(2) 0.0343(14) 0.0486(18) -0.0135(13) 0.0072(16) -0.0160(14) C27 0.0421(17) 0.0302(15) 0.0518(19) -0.0038(14) -0.0121(14) -0.0053(13) C271 0.054(2) 0.055(2) 0.046(2) -0.0062(17) -0.0116(16) -0.0077(17) C272 0.058(2) 0.0340(17) 0.069(2) -0.0047(17) -0.0206(18) -0.0036(16) C273 0.0412(18) 0.0360(16) 0.068(2) -0.0084(16) -0.0141(16) -0.0045(14) C3 0.0362(15) 0.0293(14) 0.0504(18) -0.0136(14) 0.0097(13) -0.0069(12) C31 0.0394(16) 0.0278(14) 0.0405(16) -0.0098(13) 0.0117(12) -0.0086(12) C32 0.0362(15) 0.0285(14) 0.0391(16) -0.0088(13) 0.0085(12) -0.0032(12) C33 0.0367(15) 0.0301(14) 0.0386(16) -0.0115(13) 0.0072(12) -0.0057(12) C34 0.0415(16) 0.0294(14) 0.0421(17) -0.0115(13) 0.0084(13) -0.0040(12) C35 0.0360(15) 0.0285(14) 0.0468(18) -0.0119(13) 0.0092(12) -0.0030(12) C36 0.0346(15) 0.0337(15) 0.0463(18) -0.0124(14) 0.0079(12) -0.0077(12) O32 0.0364(11) 0.0311(10) 0.0538(13) -0.0196(10) 0.0021(9) -0.0016(9) N35 0.0365(14) 0.0326(14) 0.0686(19) -0.0191(14) 0.0057(12) -0.0034(11) O351 0.0453(13) 0.0300(11) 0.0773(18) -0.0214(12) 0.0002(11) 0.0013(10) O352 0.0362(13) 0.0575(16) 0.131(3) -0.0535(18) -0.0012(14) 0.0007(12) C4 0.0384(16) 0.0325(15) 0.0449(17) -0.0167(14) 0.0037(13) -0.0004(12) C41 0.0357(15) 0.0291(14) 0.0459(17) -0.0150(13) 0.0001(12) -0.0062(12) C42 0.0354(15) 0.0254(13) 0.0386(16) -0.0099(12) -0.0044(12) -0.0035(11) C43 0.0313(14) 0.0309(14) 0.0406(16) -0.0100(13) -0.0022(12) -0.0074(12) C44 0.0406(16) 0.0310(15) 0.0450(17) -0.0068(13) -0.0025(13) -0.0136(13) C45 0.0444(17) 0.0272(15) 0.054(2) -0.0066(14) -0.0091(14) -0.0087(13) C46 0.0364(16) 0.0287(14) 0.057(2) -0.0156(14) -0.0022(14) -0.0034(12) O42 0.0378(11) 0.0296(10) 0.0360(11) -0.0076(9) -0.0050(8) -0.0030(8) C48 0.0389(16) 0.0392(16) 0.0389(16) -0.0130(14) -0.0054(12) -0.0013(13) C49 0.0461(18) 0.051(2) 0.0408(18) -0.0090(17) -0.0071(14) -0.0054(15) N49 0.075(2) 0.065(2) 0.056(2) 0.0018(19) -0.0142(17) -0.0161(19) C47 0.058(2) 0.0254(15) 0.069(2) -0.0035(16) -0.0141(18) -0.0075(15) C471 0.100(8) 0.033(4) 0.093(7) 0.012(4) -0.045(6) -0.013(4) C472 0.055(4) 0.027(3) 0.077(5) 0.000(3) -0.009(3) -0.014(3) C473 0.076(6) 0.029(3) 0.122(8) -0.003(4) 0.014(5) 0.011(3) C474 0.077(7) 0.040(5) 0.078(7) 0.008(5) 0.007(5) 0.003(4) C475 0.079(7) 0.030(4) 0.072(6) -0.008(4) -0.007(5) -0.001(4) C476 0.049(5) 0.041(5) 0.105(9) 0.008(6) -0.017(5) 0.000(4) C5 0.0352(15) 0.0276(14) 0.0363(15) -0.0080(12) 0.0021(12) -0.0014(12) C51 0.0242(13) 0.0263(13) 0.0411(16) -0.0093(12) 0.0005(11) 0.0009(10) C52 0.0283(13) 0.0301(14) 0.0358(16) -0.0053(12) 0.0010(11) -0.0001(11) C53 0.0228(13) 0.0285(14) 0.0451(17) -0.0076(13) -0.0012(11) 0.0003(11) C54 0.0255(13) 0.0315(14) 0.0425(16) -0.0095(13) -0.0027(11) 0.0005(11) C55 0.0260(13) 0.0326(14) 0.0379(16) -0.0092(13) 0.0035(11) -0.0014(11) C56 0.0260(13) 0.0266(13) 0.0396(16) -0.0078(12) 0.0033(11) -0.0005(11) O52 0.0486(12) 0.0292(10) 0.0361(11) -0.0048(9) 0.0000(9) -0.0104(9) N55 0.0303(12) 0.0395(14) 0.0366(13) -0.0136(12) 0.0031(10) -0.0044(10) O551 0.0458(12) 0.0401(12) 0.0357(11) -0.0065(10) 0.0039(9) -0.0105(10) O552 0.0458(12) 0.0468(12) 0.0391(12) -0.0169(11) 0.0015(9) -0.0036(10) C6 0.0299(14) 0.0306(14) 0.0431(17) -0.0040(13) -0.0027(12) -0.0031(12) C61 0.0287(14) 0.0280(14) 0.0433(17) -0.0023(13) -0.0032(12) -0.0058(11) C62 0.0287(14) 0.0268(13) 0.0421(16) -0.0091(12) 0.0030(11) -0.0078(11) C63 0.0272(14) 0.0251(13) 0.0469(17) -0.0042(12) -0.0026(12) -0.0069(11) C64 0.0301(14) 0.0288(14) 0.0469(18) -0.0068(13) 0.0019(12) -0.0027(12) C65 0.0316(15) 0.0348(15) 0.0491(18) -0.0076(14) 0.0031(13) -0.0048(12) C66 0.0330(15) 0.0370(16) 0.0414(17) -0.0049(13) -0.0001(12) -0.0062(12) O62 0.0288(10) 0.0307(10) 0.0476(12) -0.0112(9) 0.0047(8) -0.0100(8) C68 0.0280(14) 0.0305(14) 0.0507(18) -0.0114(13) 0.0049(12) -0.0088(11) C69 0.0306(15) 0.0368(16) 0.058(2) -0.0143(15) 0.0019(13) -0.0110(13) N69 0.0379(16) 0.0470(17) 0.101(3) -0.0364(18) 0.0066(15) -0.0055(14) C67 0.0447(19) 0.054(2) 0.052(2) -0.0157(17) 0.0074(15) 0.0040(16) C671 0.086(3) 0.053(2) 0.060(2) -0.020(2) 0.003(2) 0.023(2) C672 0.063(2) 0.059(2) 0.050(2) -0.0153(18) 0.0094(17) -0.0037(19) C673 0.043(2) 0.144(5) 0.087(3) -0.053(4) 0.017(2) -0.006(3) C7 0.0284(14) 0.0281(14) 0.0471(17) -0.0054(13) 0.0002(12) -0.0069(11) C71 0.0300(14) 0.0300(14) 0.0345(15) -0.0035(12) -0.0007(11) -0.0089(11) C72 0.0302(14) 0.0284(14) 0.0354(15) -0.0039(12) 0.0001(11) -0.0012(11) C73 0.0382(15) 0.0279(14) 0.0304(14) -0.0047(12) -0.0014(11) -0.0087(12) C74 0.0320(14) 0.0311(14) 0.0343(15) -0.0038(12) -0.0016(11) -0.0078(12) C75 0.0309(14) 0.0295(14) 0.0350(15) -0.0063(12) 0.0000(11) -0.0049(11) C76 0.0331(15) 0.0259(13) 0.0384(16) -0.0053(12) 0.0020(11) -0.0053(11) O72 0.0312(10) 0.0275(10) 0.0479(12) -0.0098(9) -0.0008(9) -0.0048(8) N75 0.0298(13) 0.0320(13) 0.0427(14) -0.0069(11) 0.0027(10) -0.0040(10) O751 0.0378(12) 0.0314(11) 0.0640(15) -0.0156(11) 0.0015(10) -0.0023(9) O752 0.0300(11) 0.0396(12) 0.0719(16) -0.0098(11) -0.0047(10) -0.0073(9) C8 0.0435(16) 0.0282(14) 0.0377(16) -0.0076(12) -0.0069(12) -0.0045(12) C81 0.0388(15) 0.0251(13) 0.0354(15) -0.0090(12) -0.0027(12) -0.0078(11) C82 0.0352(14) 0.0252(13) 0.0353(15) -0.0113(12) 0.0056(11) -0.0100(11) C83 0.0329(14) 0.0245(13) 0.0360(15) -0.0075(12) 0.0007(11) -0.0066(11) C84 0.0360(15) 0.0298(14) 0.0330(15) -0.0068(12) 0.0015(11) -0.0072(12) C85 0.0309(14) 0.0303(14) 0.0377(16) -0.0112(12) 0.0022(11) -0.0081(11) C86 0.0288(14) 0.0302(14) 0.0462(17) -0.0138(13) -0.0005(12) -0.0050(11) O82 0.0404(11) 0.0321(10) 0.0336(11) -0.0119(9) 0.0064(8) -0.0090(9) C88 0.0456(17) 0.0315(15) 0.0351(16) -0.0118(13) 0.0040(12) -0.0054(13) C89 0.0340(15) 0.0407(18) 0.0441(17) -0.0179(15) 0.0040(12) -0.0023(13) N89 0.0481(16) 0.0377(16) 0.0569(18) -0.0159(14) -0.0057(13) 0.0015(12) C87 0.0344(15) 0.0362(15) 0.0416(17) -0.0177(13) 0.0051(12) -0.0057(12) C871 0.080(3) 0.049(2) 0.067(3) -0.032(2) 0.020(2) -0.0169(19) C872 0.0364(17) 0.071(2) 0.0382(18) -0.0121(17) 0.0035(13) -0.0015(16) C873 0.0332(15) 0.0455(17) 0.0389(16) -0.0120(14) 0.0023(12) -0.0026(13) O1M 0.0474(15) 0.0739(19) 0.0721(19) -0.0126(16) 0.0025(13) -0.0022(14) C1M 0.049(2) 0.059(2) 0.076(3) -0.022(2) 0.0040(18) -0.0217(18) C1L 0.0484(18) 0.0324(16) 0.053(2) -0.0103(15) -0.0087(15) -0.0042(14) Cl1 0.0483(5) 0.0483(5) 0.0631(6) -0.0158(4) 0.0028(4) -0.0070(4) Cl2 0.0558(5) 0.0566(5) 0.0566(5) -0.0142(4) 0.0007(4) 0.0018(4) _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 C11 1.518(4) . ? C1 C43 1.521(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C11 C16 1.382(4) . ? C11 C12 1.414(4) . ? C12 O12 1.350(4) . ? C12 C13 1.409(4) . ? C13 C14 1.382(4) . ? C13 C2 1.519(4) . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 C16 1.398(4) . ? C15 N15 1.464(4) . ? C16 H16 0.9500 . ? O12 H12 0.8400 . ? N15 O151 1.231(4) . ? N15 O152 1.237(4) . ? C2 C21 1.524(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C21 C22 1.390(4) . ? C21 C26 1.404(4) . ? C22 C23 1.398(4) . ? C22 O22 1.404(3) . ? C23 C24 1.384(4) . ? C23 C3 1.520(4) . ? C24 C25 1.400(5) . ? C24 H24 0.9500 . ? C25 C26 1.388(4) . ? C25 C27 1.551(4) . ? C26 H26 0.9500 . ? O22 C28 1.444(3) . ? C28 C29 1.476(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 N29 1.141(5) . ? C27 C273 1.528(4) . ? C27 C271 1.535(5) . ? C27 C272 1.541(5) . ? C271 H27A 0.9800 . ? C271 H27B 0.9800 . ? C271 H27C 0.9800 . ? C272 H27D 0.9800 . ? C272 H27E 0.9800 . ? C272 H27F 0.9800 . ? C273 H27G 0.9800 . ? C273 H27H 0.9800 . ? C273 H27I 0.9800 . ? C3 C31 1.529(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C31 C36 1.376(4) . ? C31 C32 1.405(4) . ? C32 O32 1.355(4) . ? C32 C33 1.414(4) . ? C33 C34 1.379(4) . ? C33 C4 1.518(4) . ? C34 C35 1.384(4) . ? C34 H34 0.9500 . ? C35 C36 1.395(4) . ? C35 N35 1.461(4) . ? C36 H36 0.9500 . ? O32 H32 0.8400 . ? N35 O352 1.222(4) . ? N35 O351 1.242(3) . ? C4 C41 1.522(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C41 C42 1.392(4) . ? C41 C46 1.395(4) . ? C42 C43 1.392(4) . ? C42 O42 1.404(3) . ? C43 C44 1.399(4) . ? C44 C45 1.389(5) . ? C44 H44 0.9500 . ? C45 C46 1.396(5) . ? C45 C47 1.542(4) . ? C46 H46 0.9500 . ? O42 C48 1.428(3) . ? C48 C49 1.476(5) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 N49 1.152(5) . ? C47 C472 1.443(7) . ? C47 C476 1.454(10) . ? C47 C471 1.523(9) . ? C47 C475 1.541(9) . ? C47 C473 1.633(10) . ? C47 C474 1.635(11) . ? C471 H47A 0.9800 . ? C471 H47B 0.9800 . ? C471 H47C 0.9800 . ? C472 H47D 0.9800 . ? C472 H47E 0.9800 . ? C472 H47F 0.9800 . ? C473 H47G 0.9800 . ? C473 H47H 0.9800 . ? C473 H47I 0.9800 . ? C474 H47J 0.9800 . ? C474 H47K 0.9800 . ? C474 H47L 0.9800 . ? C475 H47M 0.9800 . ? C475 H47N 0.9800 . ? C475 H47O 0.9800 . ? C476 H47P 0.9800 . ? C476 H47Q 0.9800 . ? C476 H47R 0.9800 . ? C5 C51 1.514(4) . ? C5 C83 1.519(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C51 C56 1.370(4) . ? C51 C52 1.422(4) . ? C52 O52 1.343(4) . ? C52 C53 1.415(4) . ? C53 C54 1.379(4) . ? C53 C6 1.523(4) . ? C54 C55 1.403(4) . ? C54 H54 0.9500 . ? C55 C56 1.385(4) . ? C55 N55 1.447(4) . ? C56 H56 0.9500 . ? O52 H52 0.8400 . ? N55 O552 1.230(3) . ? N55 O551 1.239(3) . ? C6 C61 1.524(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C61 C62 1.388(4) . ? C61 C66 1.394(5) . ? C62 C63 1.399(4) . ? C62 O62 1.400(4) . ? C63 C64 1.392(4) . ? C63 C7 1.512(4) . ? C64 C65 1.394(5) . ? C64 H64 0.9500 . ? C65 C66 1.391(4) . ? C65 C67 1.544(5) . ? C66 H66 0.9500 . ? O62 C68 1.438(3) . ? C68 C69 1.462(4) . ? C68 H68A 0.9900 . ? C68 H68B 0.9900 . ? C69 N69 1.145(4) . ? C67 C672 1.527(5) . ? C67 C673 1.534(6) . ? C67 C671 1.545(6) . ? C671 H67A 0.9800 . ? C671 H67B 0.9800 . ? C671 H67C 0.9800 . ? C672 H67D 0.9800 . ? C672 H67E 0.9800 . ? C672 H67F 0.9800 . ? C673 H67G 0.9800 . ? C673 H67H 0.9800 . ? C673 H67I 0.9800 . ? C7 C71 1.516(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C71 C76 1.378(4) . ? C71 C72 1.418(4) . ? C72 O72 1.351(3) . ? C72 C73 1.405(4) . ? C73 C74 1.377(4) . ? C73 C8 1.523(4) . ? C74 C75 1.394(4) . ? C74 H74 0.9500 . ? C75 C76 1.387(4) . ? C75 N75 1.450(4) . ? C76 H76 0.9500 . ? O72 H72 0.8400 . ? N75 O751 1.235(3) . ? N75 O752 1.236(3) . ? C8 C81 1.517(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C81 C86 1.396(4) . ? C81 C82 1.397(4) . ? C82 C83 1.382(4) . ? C82 O82 1.409(4) . ? C83 C84 1.403(4) . ? C84 C85 1.386(4) . ? C84 H84 0.9500 . ? C85 C86 1.380(4) . ? C85 C87 1.542(4) . ? C86 H86 0.9500 . ? O82 C88 1.423(3) . ? C88 C89 1.471(4) . ? C88 H88A 0.9900 . ? C88 H88B 0.9900 . ? C89 N89 1.149(4) . ? C87 C873 1.529(4) . ? C87 C871 1.532(5) . ? C87 C872 1.535(5) . ? C871 H87A 0.9800 . ? C871 H87B 0.9800 . ? C871 H87C 0.9800 . ? C872 H87D 0.9800 . ? C872 H87E 0.9800 . ? C872 H87F 0.9800 . ? C873 H87G 0.9800 . ? C873 H87H 0.9800 . ? C873 H87I 0.9800 . ? O1M C1M 1.388(5) . ? O1M H1M 0.8400 . ? C1M H1MA 0.9800 . ? C1M H1MB 0.9800 . ? C1M H1MC 0.9800 . ? C1L Cl2 1.759(4) . ? C1L Cl1 1.771(4) . ? C1L H1L1 0.9900 . ? C1L H1L2 0.9900 . ? 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 C11 C1 C43 112.0(2) . . ? C11 C1 H1A 109.2 . . ? C43 C1 H1A 109.2 . . ? C11 C1 H1B 109.2 . . ? C43 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C16 C11 C12 117.8(3) . . ? C16 C11 C1 120.5(3) . . ? C12 C11 C1 121.6(3) . . ? O12 C12 C13 115.2(3) . . ? O12 C12 C11 123.0(2) . . ? C13 C12 C11 121.8(3) . . ? C14 C13 C12 118.8(3) . . ? C14 C13 C2 120.9(2) . . ? C12 C13 C2 120.3(3) . . ? C13 C14 C15 119.7(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 N15 119.0(3) . . ? C16 C15 N15 119.6(3) . . ? C11 C16 C15 120.4(3) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C12 O12 H12 109.5 . . ? O151 N15 O152 123.5(3) . . ? O151 N15 C15 118.2(2) . . ? O152 N15 C15 118.3(3) . . ? C13 C2 C21 111.6(2) . . ? C13 C2 H2A 109.3 . . ? C21 C2 H2A 109.3 . . ? C13 C2 H2B 109.3 . . ? C21 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C22 C21 C26 118.1(3) . . ? C22 C21 C2 122.5(2) . . ? C26 C21 C2 119.4(3) . . ? C21 C22 C23 121.4(3) . . ? C21 C22 O22 119.5(2) . . ? C23 C22 O22 118.9(3) . . ? C24 C23 C22 118.2(3) . . ? C24 C23 C3 120.3(3) . . ? C22 C23 C3 121.4(3) . . ? C23 C24 C25 122.5(3) . . ? C23 C24 H24 118.7 . . ? C25 C24 H24 118.7 . . ? C26 C25 C24 117.3(3) . . ? C26 C25 C27 122.3(3) . . ? C24 C25 C27 120.4(3) . . ? C25 C26 C21 122.2(3) . . ? C25 C26 H26 118.9 . . ? C21 C26 H26 118.9 . . ? C22 O22 C28 116.6(2) . . ? O22 C28 C29 109.7(2) . . ? O22 C28 H28A 109.7 . . ? C29 C28 H28A 109.7 . . ? O22 C28 H28B 109.7 . . ? C29 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? N29 C29 C28 176.1(3) . . ? C273 C27 C271 108.1(3) . . ? C273 C27 C272 109.0(3) . . ? C271 C27 C272 108.7(3) . . ? C273 C27 C25 109.4(3) . . ? C271 C27 C25 111.6(3) . . ? C272 C27 C25 110.0(3) . . ? C27 C271 H27A 109.5 . . ? C27 C271 H27B 109.5 . . ? H27A C271 H27B 109.5 . . ? C27 C271 H27C 109.5 . . ? H27A C271 H27C 109.5 . . ? H27B C271 H27C 109.5 . . ? C27 C272 H27D 109.5 . . ? C27 C272 H27E 109.5 . . ? H27D C272 H27E 109.5 . . ? C27 C272 H27F 109.5 . . ? H27D C272 H27F 109.5 . . ? H27E C272 H27F 109.5 . . ? C27 C273 H27G 109.5 . . ? C27 C273 H27H 109.5 . . ? H27G C273 H27H 109.5 . . ? C27 C273 H27I 109.5 . . ? H27G C273 H27I 109.5 . . ? H27H C273 H27I 109.5 . . ? C23 C3 C31 112.5(3) . . ? C23 C3 H3A 109.1 . . ? C31 C3 H3A 109.1 . . ? C23 C3 H3B 109.1 . . ? C31 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C36 C31 C32 118.6(3) . . ? C36 C31 C3 119.3(3) . . ? C32 C31 C3 122.1(3) . . ? O32 C32 C31 123.4(3) . . ? O32 C32 C33 114.8(3) . . ? C31 C32 C33 121.7(3) . . ? C34 C33 C32 118.4(3) . . ? C34 C33 C4 121.6(3) . . ? C32 C33 C4 120.0(3) . . ? C33 C34 C35 119.6(3) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C34 C35 C36 122.2(3) . . ? C34 C35 N35 119.7(3) . . ? C36 C35 N35 118.0(3) . . ? C31 C36 C35 119.5(3) . . ? C31 C36 H36 120.3 . . ? C35 C36 H36 120.3 . . ? C32 O32 H32 109.5 . . ? O352 N35 O351 123.1(3) . . ? O352 N35 C35 118.9(3) . . ? O351 N35 C35 117.9(3) . . ? C33 C4 C41 112.3(3) . . ? C33 C4 H4A 109.1 . . ? C41 C4 H4A 109.1 . . ? C33 C4 H4B 109.1 . . ? C41 C4 H4B 109.1 . . ? H4A C4 H4B 107.9 . . ? C42 C41 C46 117.7(3) . . ? C42 C41 C4 122.9(3) . . ? C46 C41 C4 119.4(3) . . ? C43 C42 C41 122.1(3) . . ? C43 C42 O42 117.9(3) . . ? C41 C42 O42 119.9(3) . . ? C42 C43 C44 117.7(3) . . ? C42 C43 C1 121.7(3) . . ? C44 C43 C1 120.6(3) . . ? C45 C44 C43 122.4(3) . . ? C45 C44 H44 118.8 . . ? C43 C44 H44 118.8 . . ? C44 C45 C46 117.4(3) . . ? C44 C45 C47 121.5(3) . . ? C46 C45 C47 121.0(3) . . ? C41 C46 C45 122.3(3) . . ? C41 C46 H46 118.8 . . ? C45 C46 H46 118.8 . . ? C42 O42 C48 114.8(2) . . ? O42 C48 C49 106.4(2) . . ? O42 C48 H48A 110.4 . . ? C49 C48 H48A 110.4 . . ? O42 C48 H48B 110.4 . . ? C49 C48 H48B 110.4 . . ? H48A C48 H48B 108.6 . . ? N49 C49 C48 179.0(4) . . ? C472 C47 C476 134.3(5) . . ? C472 C47 C471 115.5(6) . . ? C476 C47 C471 46.4(6) . . ? C472 C47 C475 51.2(5) . . ? C476 C47 C475 114.2(7) . . ? C471 C47 C475 144.1(5) . . ? C472 C47 C45 112.2(4) . . ? C476 C47 C45 113.4(5) . . ? C471 C47 C45 108.8(4) . . ? C475 C47 C45 107.0(4) . . ? C472 C47 C473 105.9(5) . . ? C476 C47 C473 58.4(7) . . ? C471 C47 C473 103.7(7) . . ? C475 C47 C473 59.9(6) . . ? C45 C47 C473 110.3(4) . . ? C472 C47 C474 53.3(5) . . ? C476 C47 C474 107.7(7) . . ? C471 C47 C474 66.7(7) . . ? C475 C47 C474 103.4(6) . . ? C45 C47 C474 110.7(4) . . ? C473 C47 C474 138.7(5) . . ? C47 C471 H47A 109.5 . . ? C47 C471 H47B 109.5 . . ? H47A C471 H47B 109.5 . . ? C47 C471 H47C 109.5 . . ? H47A C471 H47C 109.5 . . ? H47B C471 H47C 109.5 . . ? C47 C472 H47D 109.5 . . ? C47 C472 H47E 109.5 . . ? H47D C472 H47E 109.5 . . ? C47 C472 H47F 109.5 . . ? H47D C472 H47F 109.5 . . ? H47E C472 H47F 109.5 . . ? C47 C473 H47G 109.5 . . ? C47 C473 H47H 109.5 . . ? H47G C473 H47H 109.5 . . ? C47 C473 H47I 109.5 . . ? H47G C473 H47I 109.5 . . ? H47H C473 H47I 109.5 . . ? C47 C474 H47J 109.5 . . ? C47 C474 H47K 109.5 . . ? H47J C474 H47K 109.5 . . ? C47 C474 H47L 109.5 . . ? H47J C474 H47L 109.5 . . ? H47K C474 H47L 109.5 . . ? C47 C475 H47M 109.5 . . ? C47 C475 H47N 109.5 . . ? H47M C475 H47N 109.5 . . ? C47 C475 H47O 109.5 . . ? H47M C475 H47O 109.5 . . ? H47N C475 H47O 109.5 . . ? C47 C476 H47P 109.5 . . ? C47 C476 H47Q 109.5 . . ? H47P C476 H47Q 109.5 . . ? C47 C476 H47R 109.5 . . ? H47P C476 H47R 109.5 . . ? H47Q C476 H47R 109.5 . . ? C51 C5 C83 109.6(2) . . ? C51 C5 H5A 109.7 . . ? C83 C5 H5A 109.7 . . ? C51 C5 H5B 109.7 . . ? C83 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C56 C51 C52 118.9(3) . . ? C56 C51 C5 122.3(3) . . ? C52 C51 C5 118.7(3) . . ? O52 C52 C53 123.5(3) . . ? O52 C52 C51 115.7(2) . . ? C53 C52 C51 120.8(3) . . ? C54 C53 C52 118.9(3) . . ? C54 C53 C6 119.7(3) . . ? C52 C53 C6 121.4(3) . . ? C53 C54 C55 119.5(3) . . ? C53 C54 H54 120.2 . . ? C55 C54 H54 120.2 . . ? C56 C55 C54 121.7(3) . . ? C56 C55 N55 119.2(3) . . ? C54 C55 N55 119.2(3) . . ? C51 C56 C55 120.1(3) . . ? C51 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? C52 O52 H52 109.5 . . ? O552 N55 O551 123.0(3) . . ? O552 N55 C55 118.8(2) . . ? O551 N55 C55 118.1(2) . . ? C53 C6 C61 113.0(2) . . ? C53 C6 H6A 109.0 . . ? C61 C6 H6A 109.0 . . ? C53 C6 H6B 109.0 . . ? C61 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C62 C61 C66 118.2(3) . . ? C62 C61 C6 121.9(3) . . ? C66 C61 C6 119.9(3) . . ? C61 C62 C63 122.5(3) . . ? C61 C62 O62 118.6(2) . . ? C63 C62 O62 118.9(3) . . ? C64 C63 C62 116.8(3) . . ? C64 C63 C7 120.9(3) . . ? C62 C63 C7 122.2(3) . . ? C63 C64 C65 122.8(3) . . ? C63 C64 H64 118.6 . . ? C65 C64 H64 118.6 . . ? C66 C65 C64 117.9(3) . . ? C66 C65 C67 122.8(3) . . ? C64 C65 C67 119.4(3) . . ? C65 C66 C61 121.7(3) . . ? C65 C66 H66 119.2 . . ? C61 C66 H66 119.2 . . ? C62 O62 C68 113.9(2) . . ? O62 C68 C69 106.3(2) . . ? O62 C68 H68A 110.5 . . ? C69 C68 H68A 110.5 . . ? O62 C68 H68B 110.5 . . ? C69 C68 H68B 110.5 . . ? H68A C68 H68B 108.7 . . ? N69 C69 C68 178.2(4) . . ? C672 C67 C673 108.5(4) . . ? C672 C67 C65 112.4(3) . . ? C673 C67 C65 108.0(3) . . ? C672 C67 C671 107.7(3) . . ? C673 C67 C671 110.4(4) . . ? C65 C67 C671 109.9(3) . . ? C67 C671 H67A 109.5 . . ? C67 C671 H67B 109.5 . . ? H67A C671 H67B 109.5 . . ? C67 C671 H67C 109.5 . . ? H67A C671 H67C 109.5 . . ? H67B C671 H67C 109.5 . . ? C67 C672 H67D 109.5 . . ? C67 C672 H67E 109.5 . . ? H67D C672 H67E 109.5 . . ? C67 C672 H67F 109.5 . . ? H67D C672 H67F 109.5 . . ? H67E C672 H67F 109.5 . . ? C67 C673 H67G 109.5 . . ? C67 C673 H67H 109.5 . . ? H67G C673 H67H 109.5 . . ? C67 C673 H67I 109.5 . . ? H67G C673 H67I 109.5 . . ? H67H C673 H67I 109.5 . . ? C63 C7 C71 112.0(2) . . ? C63 C7 H7A 109.2 . . ? C71 C7 H7A 109.2 . . ? C63 C7 H7B 109.2 . . ? C71 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C76 C71 C72 118.7(2) . . ? C76 C71 C7 121.5(3) . . ? C72 C71 C7 119.8(3) . . ? O72 C72 C73 121.7(2) . . ? O72 C72 C71 117.1(2) . . ? C73 C72 C71 121.3(3) . . ? C74 C73 C72 118.8(3) . . ? C74 C73 C8 120.5(2) . . ? C72 C73 C8 120.7(3) . . ? C73 C74 C75 119.7(3) . . ? C73 C74 H74 120.1 . . ? C75 C74 H74 120.1 . . ? C76 C75 C74 121.9(3) . . ? C76 C75 N75 119.3(2) . . ? C74 C75 N75 118.8(2) . . ? C71 C76 C75 119.7(3) . . ? C71 C76 H76 120.2 . . ? C75 C76 H76 120.2 . . ? C72 O72 H72 109.5 . . ? O751 N75 O752 121.8(2) . . ? O751 N75 C75 119.2(2) . . ? O752 N75 C75 119.0(2) . . ? C81 C8 C73 109.9(2) . . ? C81 C8 H8A 109.7 . . ? C73 C8 H8A 109.7 . . ? C81 C8 H8B 109.7 . . ? C73 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C86 C81 C82 117.8(3) . . ? C86 C81 C8 118.7(3) . . ? C82 C81 C8 122.9(3) . . ? C83 C82 C81 122.1(3) . . ? C83 C82 O82 119.5(3) . . ? C81 C82 O82 118.0(3) . . ? C82 C83 C84 117.5(3) . . ? C82 C83 C5 123.2(3) . . ? C84 C83 C5 119.0(3) . . ? C85 C84 C83 122.5(3) . . ? C85 C84 H84 118.7 . . ? C83 C84 H84 118.7 . . ? C86 C85 C84 117.7(3) . . ? C86 C85 C87 120.4(3) . . ? C84 C85 C87 121.7(3) . . ? C85 C86 C81 122.3(3) . . ? C85 C86 H86 118.9 . . ? C81 C86 H86 118.9 . . ? C82 O82 C88 115.7(2) . . ? O82 C88 C89 111.9(2) . . ? O82 C88 H88A 109.2 . . ? C89 C88 H88A 109.2 . . ? O82 C88 H88B 109.2 . . ? C89 C88 H88B 109.2 . . ? H88A C88 H88B 107.9 . . ? N89 C89 C88 179.0(4) . . ? C873 C87 C871 110.4(3) . . ? C873 C87 C872 107.3(3) . . ? C871 C87 C872 108.0(3) . . ? C873 C87 C85 110.0(2) . . ? C871 C87 C85 108.7(3) . . ? C872 C87 C85 112.4(3) . . ? C87 C871 H87A 109.5 . . ? C87 C871 H87B 109.5 . . ? H87A C871 H87B 109.5 . . ? C87 C871 H87C 109.5 . . ? H87A C871 H87C 109.5 . . ? H87B C871 H87C 109.5 . . ? C87 C872 H87D 109.5 . . ? C87 C872 H87E 109.5 . . ? H87D C872 H87E 109.5 . . ? C87 C872 H87F 109.5 . . ? H87D C872 H87F 109.5 . . ? H87E C872 H87F 109.5 . . ? C87 C873 H87G 109.5 . . ? C87 C873 H87H 109.5 . . ? H87G C873 H87H 109.5 . . ? C87 C873 H87I 109.5 . . ? H87G C873 H87I 109.5 . . ? H87H C873 H87I 109.5 . . ? C1M O1M H1M 109.5 . . ? O1M C1M H1MA 109.5 . . ? O1M C1M H1MB 109.5 . . ? H1MA C1M H1MB 109.5 . . ? O1M C1M H1MC 109.5 . . ? H1MA C1M H1MC 109.5 . . ? H1MB C1M H1MC 109.5 . . ? Cl2 C1L Cl1 111.55(18) . . ? Cl2 C1L H1L1 109.3 . . ? Cl1 C1L H1L1 109.3 . . ? Cl2 C1L H1L2 109.3 . . ? Cl1 C1L H1L2 109.3 . . ? H1L1 C1L H1L2 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C43 C1 C11 C16 -102.5(3) . . . . ? C43 C1 C11 C12 75.4(3) . . . . ? C16 C11 C12 O12 -178.3(3) . . . . ? C1 C11 C12 O12 3.8(4) . . . . ? C16 C11 C12 C13 1.0(4) . . . . ? C1 C11 C12 C13 -177.0(3) . . . . ? O12 C12 C13 C14 -179.9(2) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? O12 C12 C13 C2 -0.6(4) . . . . ? C11 C12 C13 C2 -179.9(2) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C2 C13 C14 C15 179.0(3) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C13 C14 C15 N15 -178.5(3) . . . . ? C12 C11 C16 C15 -1.8(4) . . . . ? C1 C11 C16 C15 176.2(3) . . . . ? C14 C15 C16 C11 0.9(5) . . . . ? N15 C15 C16 C11 -179.7(3) . . . . ? C14 C15 N15 O151 161.7(3) . . . . ? C16 C15 N15 O151 -17.7(4) . . . . ? C14 C15 N15 O152 -18.6(4) . . . . ? C16 C15 N15 O152 162.0(3) . . . . ? C14 C13 C2 C21 94.1(3) . . . . ? C12 C13 C2 C21 -85.2(3) . . . . ? C13 C2 C21 C22 106.5(3) . . . . ? C13 C2 C21 C26 -72.4(3) . . . . ? C26 C21 C22 C23 5.7(4) . . . . ? C2 C21 C22 C23 -173.3(2) . . . . ? C26 C21 C22 O22 -179.7(2) . . . . ? C2 C21 C22 O22 1.4(4) . . . . ? C21 C22 C23 C24 -4.7(4) . . . . ? O22 C22 C23 C24 -179.4(2) . . . . ? C21 C22 C23 C3 171.9(2) . . . . ? O22 C22 C23 C3 -2.8(4) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C3 C23 C24 C25 -176.6(3) . . . . ? C23 C24 C25 C26 3.4(4) . . . . ? C23 C24 C25 C27 -177.8(3) . . . . ? C24 C25 C26 C21 -2.4(4) . . . . ? C27 C25 C26 C21 178.9(3) . . . . ? C22 C21 C26 C25 -2.1(4) . . . . ? C2 C21 C26 C25 177.0(2) . . . . ? C21 C22 O22 C28 87.6(3) . . . . ? C23 C22 O22 C28 -97.6(3) . . . . ? C22 O22 C28 C29 105.3(3) . . . . ? O22 C28 C29 N29 19(6) . . . . ? C26 C25 C27 C273 -123.4(3) . . . . ? C24 C25 C27 C273 57.9(4) . . . . ? C26 C25 C27 C271 -3.8(4) . . . . ? C24 C25 C27 C271 177.5(3) . . . . ? C26 C25 C27 C272 116.9(3) . . . . ? C24 C25 C27 C272 -61.8(4) . . . . ? C24 C23 C3 C31 80.6(3) . . . . ? C22 C23 C3 C31 -95.9(3) . . . . ? C23 C3 C31 C36 -106.3(3) . . . . ? C23 C3 C31 C32 74.9(4) . . . . ? C36 C31 C32 O32 -176.8(3) . . . . ? C3 C31 C32 O32 2.0(5) . . . . ? C36 C31 C32 C33 1.7(5) . . . . ? C3 C31 C32 C33 -179.4(3) . . . . ? O32 C32 C33 C34 177.3(3) . . . . ? C31 C32 C33 C34 -1.4(5) . . . . ? O32 C32 C33 C4 -2.6(4) . . . . ? C31 C32 C33 C4 178.8(3) . . . . ? C32 C33 C34 C35 0.2(5) . . . . ? C4 C33 C34 C35 -180.0(3) . . . . ? C33 C34 C35 C36 0.6(5) . . . . ? C33 C34 C35 N35 -178.8(3) . . . . ? C32 C31 C36 C35 -0.9(5) . . . . ? C3 C31 C36 C35 -179.8(3) . . . . ? C34 C35 C36 C31 -0.3(5) . . . . ? N35 C35 C36 C31 179.2(3) . . . . ? C34 C35 N35 O352 179.3(3) . . . . ? C36 C35 N35 O352 -0.2(5) . . . . ? C34 C35 N35 O351 1.0(5) . . . . ? C36 C35 N35 O351 -178.5(3) . . . . ? C34 C33 C4 C41 98.5(3) . . . . ? C32 C33 C4 C41 -81.6(4) . . . . ? C33 C4 C41 C42 107.0(3) . . . . ? C33 C4 C41 C46 -72.2(3) . . . . ? C46 C41 C42 C43 5.2(4) . . . . ? C4 C41 C42 C43 -174.0(3) . . . . ? C46 C41 C42 O42 -178.0(2) . . . . ? C4 C41 C42 O42 2.9(4) . . . . ? C41 C42 C43 C44 -4.8(4) . . . . ? O42 C42 C43 C44 178.2(2) . . . . ? C41 C42 C43 C1 172.4(2) . . . . ? O42 C42 C43 C1 -4.6(4) . . . . ? C11 C1 C43 C42 -96.8(3) . . . . ? C11 C1 C43 C44 80.3(3) . . . . ? C42 C43 C44 C45 0.0(4) . . . . ? C1 C43 C44 C45 -177.2(3) . . . . ? C43 C44 C45 C46 4.1(4) . . . . ? C43 C44 C45 C47 -175.4(3) . . . . ? C42 C41 C46 C45 -0.7(4) . . . . ? C4 C41 C46 C45 178.5(3) . . . . ? C44 C45 C46 C41 -3.8(4) . . . . ? C47 C45 C46 C41 175.8(3) . . . . ? C43 C42 O42 C48 -104.1(3) . . . . ? C41 C42 O42 C48 78.9(3) . . . . ? C42 O42 C48 C49 -149.9(3) . . . . ? O42 C48 C49 N49 37(24) . . . . ? C44 C45 C47 C472 54.2(6) . . . . ? C46 C45 C47 C472 -125.3(5) . . . . ? C44 C45 C47 C476 -124.6(8) . . . . ? C46 C45 C47 C476 55.9(8) . . . . ? C44 C45 C47 C471 -74.9(7) . . . . ? C46 C45 C47 C471 105.6(7) . . . . ? C44 C45 C47 C475 108.6(5) . . . . ? C46 C45 C47 C475 -71.0(6) . . . . ? C44 C45 C47 C473 172.1(5) . . . . ? C46 C45 C47 C473 -7.5(6) . . . . ? C44 C45 C47 C474 -3.4(6) . . . . ? C46 C45 C47 C474 177.0(5) . . . . ? C83 C5 C51 C56 101.0(3) . . . . ? C83 C5 C51 C52 -75.1(3) . . . . ? C56 C51 C52 O52 177.1(2) . . . . ? C5 C51 C52 O52 -6.7(4) . . . . ? C56 C51 C52 C53 -3.5(4) . . . . ? C5 C51 C52 C53 172.7(2) . . . . ? O52 C52 C53 C54 -177.9(3) . . . . ? C51 C52 C53 C54 2.7(4) . . . . ? O52 C52 C53 C6 0.9(4) . . . . ? C51 C52 C53 C6 -178.5(2) . . . . ? C52 C53 C54 C55 -0.4(4) . . . . ? C6 C53 C54 C55 -179.2(3) . . . . ? C53 C54 C55 C56 -1.2(4) . . . . ? C53 C54 C55 N55 177.7(2) . . . . ? C52 C51 C56 C55 1.9(4) . . . . ? C5 C51 C56 C55 -174.2(3) . . . . ? C54 C55 C56 C51 0.4(4) . . . . ? N55 C55 C56 C51 -178.5(2) . . . . ? C56 C55 N55 O552 -168.2(3) . . . . ? C54 C55 N55 O552 12.8(4) . . . . ? C56 C55 N55 O551 12.4(4) . . . . ? C54 C55 N55 O551 -166.6(3) . . . . ? C54 C53 C6 C61 -106.9(3) . . . . ? C52 C53 C6 C61 74.3(4) . . . . ? C53 C6 C61 C62 -98.0(3) . . . . ? C53 C6 C61 C66 81.0(3) . . . . ? C66 C61 C62 C63 -3.4(4) . . . . ? C6 C61 C62 C63 175.7(3) . . . . ? C66 C61 C62 O62 179.3(2) . . . . ? C6 C61 C62 O62 -1.6(4) . . . . ? C61 C62 C63 C64 3.7(4) . . . . ? O62 C62 C63 C64 -179.1(2) . . . . ? C61 C62 C63 C7 -174.7(3) . . . . ? O62 C62 C63 C7 2.5(4) . . . . ? C62 C63 C64 C65 -0.7(4) . . . . ? C7 C63 C64 C65 177.7(3) . . . . ? C63 C64 C65 C66 -2.4(4) . . . . ? C63 C64 C65 C67 178.1(3) . . . . ? C64 C65 C66 C61 2.7(4) . . . . ? C67 C65 C66 C61 -177.7(3) . . . . ? C62 C61 C66 C65 0.1(4) . . . . ? C6 C61 C66 C65 -179.0(3) . . . . ? C61 C62 O62 C68 -91.3(3) . . . . ? C63 C62 O62 C68 91.3(3) . . . . ? C62 O62 C68 C69 152.4(3) . . . . ? O62 C68 C69 N69 -28(12) . . . . ? C66 C65 C67 C672 9.8(5) . . . . ? C64 C65 C67 C672 -170.7(3) . . . . ? C66 C65 C67 C673 -109.8(4) . . . . ? C64 C65 C67 C673 69.7(5) . . . . ? C66 C65 C67 C671 129.7(4) . . . . ? C64 C65 C67 C671 -50.8(4) . . . . ? C64 C63 C7 C71 -71.2(3) . . . . ? C62 C63 C7 C71 107.1(3) . . . . ? C63 C7 C71 C76 98.9(3) . . . . ? C63 C7 C71 C72 -79.6(3) . . . . ? C76 C71 C72 O72 -179.6(3) . . . . ? C7 C71 C72 O72 -1.0(4) . . . . ? C76 C71 C72 C73 0.2(4) . . . . ? C7 C71 C72 C73 178.9(3) . . . . ? O72 C72 C73 C74 -179.9(3) . . . . ? C71 C72 C73 C74 0.3(4) . . . . ? O72 C72 C73 C8 3.1(4) . . . . ? C71 C72 C73 C8 -176.8(3) . . . . ? C72 C73 C74 C75 -0.9(4) . . . . ? C8 C73 C74 C75 176.2(3) . . . . ? C73 C74 C75 C76 0.9(5) . . . . ? C73 C74 C75 N75 -178.5(3) . . . . ? C72 C71 C76 C75 -0.2(4) . . . . ? C7 C71 C76 C75 -178.8(3) . . . . ? C74 C75 C76 C71 -0.4(5) . . . . ? N75 C75 C76 C71 179.1(3) . . . . ? C76 C75 N75 O751 2.8(4) . . . . ? C74 C75 N75 O751 -177.7(3) . . . . ? C76 C75 N75 O752 -176.4(3) . . . . ? C74 C75 N75 O752 3.1(4) . . . . ? C74 C73 C8 C81 -108.3(3) . . . . ? C72 C73 C8 C81 68.8(4) . . . . ? C73 C8 C81 C86 63.1(3) . . . . ? C73 C8 C81 C82 -108.8(3) . . . . ? C86 C81 C82 C83 -0.5(4) . . . . ? C8 C81 C82 C83 171.4(2) . . . . ? C86 C81 C82 O82 -172.6(2) . . . . ? C8 C81 C82 O82 -0.6(4) . . . . ? C81 C82 C83 C84 0.8(4) . . . . ? O82 C82 C83 C84 172.8(2) . . . . ? C81 C82 C83 C5 -172.5(2) . . . . ? O82 C82 C83 C5 -0.5(4) . . . . ? C51 C5 C83 C82 118.7(3) . . . . ? C51 C5 C83 C84 -54.5(3) . . . . ? C82 C83 C84 C85 -1.6(4) . . . . ? C5 C83 C84 C85 172.0(2) . . . . ? C83 C84 C85 C86 2.1(4) . . . . ? C83 C84 C85 C87 -172.7(3) . . . . ? C84 C85 C86 C81 -1.8(4) . . . . ? C87 C85 C86 C81 173.1(2) . . . . ? C82 C81 C86 C85 1.0(4) . . . . ? C8 C81 C86 C85 -171.3(3) . . . . ? C83 C82 O82 C88 100.0(3) . . . . ? C81 C82 O82 C88 -87.7(3) . . . . ? C82 O82 C88 C89 -75.3(3) . . . . ? O82 C88 C89 N89 35(20) . . . . ? C86 C85 C87 C873 59.3(3) . . . . ? C84 C85 C87 C873 -126.1(3) . . . . ? C86 C85 C87 C871 -61.7(4) . . . . ? C84 C85 C87 C871 112.9(3) . . . . ? C86 C85 C87 C872 178.8(3) . . . . ? C84 C85 C87 C872 -6.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O42 0.84 1.94 2.720(3) 154.9 . O32 H32 O22 0.84 1.87 2.693(3) 165.3 . O52 H52 O62 0.84 1.91 2.724(3) 162.5 . O72 H72 O82 0.84 2.13 2.924(3) 158.7 . O1M H1M O751 0.84 2.46 3.273(4) 163.5 1_655 O1M H1M O752 0.84 2.73 3.285(4) 124.6 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.012 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.085 data_boeh24 _database_code_depnum_ccdc_archive 'CCDC 272780' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H48 N4 O8' _chemical_formula_weight 784.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3157(11) _cell_length_b 12.4728(12) _cell_length_c 17.753(2) _cell_angle_alpha 99.611(8) _cell_angle_beta 103.810(8) _cell_angle_gamma 99.245(8) _cell_volume 2138.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17034 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27339 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 26.91 _reflns_number_total 9052 _reflns_number_gt 5324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _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 Rfactors 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^)+(0.1350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9052 _refine_ls_number_parameters 533 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.2161 _refine_ls_wR_factor_gt 0.1962 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6705(2) 1.02790(19) 0.75093(13) 0.0593(5) Uani 1 1 d . . . H1A H 0.7269 1.0552 0.7187 0.071 Uiso 1 1 calc R . . H1B H 0.6398 1.0902 0.7765 0.071 Uiso 1 1 calc R . . C11 C 0.7541(2) 0.97849(17) 0.81353(12) 0.0535(5) Uani 1 1 d . . . C12 C 0.8301(2) 0.90087(18) 0.79163(12) 0.0536(5) Uani 1 1 d . . . C13 C 0.8898(2) 0.83896(17) 0.84396(13) 0.0550(5) Uani 1 1 d . . . C14 C 0.8794(2) 0.86097(19) 0.92056(13) 0.0581(5) Uani 1 1 d . . . H14 H 0.9168 0.8205 0.9566 0.070 Uiso 1 1 calc R . . C15 C 0.8134(2) 0.94314(18) 0.94386(12) 0.0552(5) Uani 1 1 d . . . C16 C 0.7495(2) 1.00124(18) 0.89157(13) 0.0554(5) Uani 1 1 d . . . H16 H 0.7038 1.0550 0.9087 0.066 Uiso 1 1 calc R . . N15 N 0.8088(2) 0.96920(19) 1.02653(12) 0.0676(5) Uani 1 1 d . . . O151 O 0.7717(2) 1.05343(18) 1.04982(11) 0.0896(6) Uani 1 1 d . . . O152 O 0.8444(3) 0.9076(2) 1.06970(12) 0.1030(7) Uani 1 1 d . . . O12 O 0.83881(17) 0.88112(15) 0.71461(9) 0.0678(4) Uani 1 1 d . . . C17 C 0.9590(4) 0.9478(4) 0.7055(2) 0.1030(10) Uani 1 1 d . . . H17A H 0.9567 1.0257 0.7204 0.124 Uiso 1 1 calc R . . H17B H 1.0390 0.9343 0.7411 0.124 Uiso 1 1 calc R . . C18 C 0.9697(8) 0.9247(7) 0.6281(4) 0.212(4) Uani 1 1 d . . . H18 H 0.9098 0.8601 0.5969 0.254 Uiso 1 1 calc R . . C19 C 1.0356(16) 0.9677(15) 0.5952(7) 0.413(11) Uani 1 1 d . . . H19A H 1.0990 1.0331 0.6211 0.495 Uiso 1 1 calc R . . H19B H 1.0266 0.9378 0.5422 0.495 Uiso 1 1 calc R . . C2 C 0.9598(2) 0.74714(19) 0.81701(15) 0.0618(5) Uani 1 1 d . . . H2A H 0.9637 0.7479 0.7630 0.074 Uiso 1 1 calc R . . H2B H 1.0529 0.7632 0.8504 0.074 Uiso 1 1 calc R . . C21 C 0.8911(2) 0.63213(18) 0.81959(13) 0.0568(5) Uani 1 1 d . . . C22 C 0.7506(2) 0.59386(18) 0.78993(12) 0.0559(5) Uani 1 1 d . . . C23 C 0.6847(2) 0.49098(18) 0.79764(14) 0.0618(5) Uani 1 1 d . . . C24 C 0.7678(3) 0.4218(2) 0.82755(15) 0.0678(6) Uani 1 1 d . . . H24 H 0.7264 0.3521 0.8321 0.081 Uiso 1 1 calc R . . C25 C 0.9098(3) 0.45145(19) 0.85108(14) 0.0654(6) Uani 1 1 d . . . C26 C 0.9684(2) 0.55861(19) 0.84886(14) 0.0638(6) Uani 1 1 d . . . H26 H 1.0627 0.5823 0.8676 0.077 Uiso 1 1 calc R . . C27 C 0.9966(3) 0.3675(2) 0.87540(17) 0.0817(8) Uani 1 1 d . . . C271 C 0.9928(6) 0.2879(4) 0.7999(3) 0.160(2) Uani 1 1 d . . . H27A H 0.8997 0.2562 0.7706 0.240 Uiso 1 1 calc R . . H27B H 1.0387 0.2297 0.8133 0.240 Uiso 1 1 calc R . . H27C H 1.0377 0.3275 0.7681 0.240 Uiso 1 1 calc R . . C272 C 0.9296(5) 0.2952(4) 0.9221(3) 0.1450(18) Uani 1 1 d . . . H27D H 0.8386 0.2590 0.8911 0.217 Uiso 1 1 calc R . . H27E H 0.9258 0.3406 0.9706 0.217 Uiso 1 1 calc R . . H27F H 0.9818 0.2401 0.9344 0.217 Uiso 1 1 calc R . . C273 C 1.1367(4) 0.4210(4) 0.9254(4) 0.182(3) Uani 1 1 d . . . H27G H 1.1861 0.3647 0.9388 0.273 Uiso 1 1 calc R . . H27H H 1.1319 0.4675 0.9731 0.273 Uiso 1 1 calc R . . H27I H 1.1829 0.4654 0.8965 0.273 Uiso 1 1 calc R . . O22 O 0.67455(15) 0.66441(12) 0.75467(9) 0.0599(4) Uani 1 1 d . . . C28 C 0.6348(3) 0.6377(2) 0.67083(16) 0.0793(7) Uani 1 1 d . . . H28A H 0.5923 0.6955 0.6515 0.095 Uiso 1 1 calc R . . H28B H 0.5672 0.5686 0.6528 0.095 Uiso 1 1 calc R . . C29 C 0.7489(4) 0.6261(3) 0.63660(18) 0.0963(9) Uani 1 1 d . . . N29 N 0.8385(5) 0.6145(4) 0.6109(2) 0.1413(14) Uani 1 1 d . . . C3 C 0.5300(3) 0.4551(2) 0.77465(18) 0.0747(7) Uani 1 1 d . . . H3A H 0.4960 0.4362 0.7172 0.090 Uiso 1 1 calc R . . H3B H 0.5053 0.3888 0.7943 0.090 Uiso 1 1 calc R . . C31 C 0.4620(2) 0.54447(19) 0.80729(16) 0.0662(6) Uani 1 1 d . . . C32 C 0.3713(2) 0.5915(2) 0.75760(15) 0.0648(6) Uani 1 1 d . . . C33 C 0.3252(2) 0.6851(2) 0.78508(15) 0.0643(6) Uani 1 1 d . . . C34 C 0.3595(2) 0.7262(2) 0.86641(15) 0.0674(6) Uani 1 1 d . . . H34 H 0.3289 0.7878 0.8871 0.081 Uiso 1 1 calc R . . C35 C 0.4402(3) 0.6740(2) 0.91637(16) 0.0700(6) Uani 1 1 d . . . C36 C 0.4946(2) 0.5864(2) 0.88844(16) 0.0703(6) Uani 1 1 d . . . H36 H 0.5523 0.5558 0.9236 0.084 Uiso 1 1 calc R . . N35 N 0.4713(3) 0.7152(3) 1.00251(16) 0.0943(8) Uani 1 1 d . . . O351 O 0.5377(4) 0.6679(3) 1.04659(16) 0.1490(13) Uani 1 1 d . . . O352 O 0.4265(4) 0.7923(3) 1.02728(16) 0.1588(15) Uani 1 1 d . . . O32 O 0.33187(19) 0.54776(16) 0.67713(12) 0.0850(5) Uani 1 1 d . . . C37 C 0.2138(6) 0.4569(5) 0.6550(4) 0.183(3) Uani 1 1 d . A . H37A H 0.2382 0.4048 0.6881 0.220 Uiso 1 1 calc R . . H37B H 0.1430 0.4878 0.6728 0.220 Uiso 1 1 calc R . . C38 C 0.1647(10) 0.4072(10) 0.5966(7) 0.304(7) Uani 1 1 d . . . H38 H 0.1273 0.4449 0.5585 0.365 Uiso 0.513(13) 1 calc PR A 1 H38' H 0.2099 0.3564 0.5750 0.365 Uiso 0.487(13) 1 calc PR A 2 C39 C 0.1500(15) 0.2893(11) 0.5699(9) 0.198(7) Uani 0.513(13) 1 d P A 1 H39A H 0.1854 0.2472 0.6053 0.237 Uiso 0.513(13) 1 calc PR A 1 H39B H 0.1050 0.2552 0.5173 0.237 Uiso 0.513(13) 1 calc PR A 1 C39' C 0.0295(11) 0.4149(15) 0.5483(8) 0.206(8) Uani 0.487(13) 1 d P A 2 H39C H -0.0180 0.4650 0.5684 0.247 Uiso 0.487(13) 1 calc PR A 2 H39D H -0.0080 0.3696 0.4979 0.247 Uiso 0.487(13) 1 calc PR A 2 C4 C 0.2477(2) 0.7462(2) 0.72802(16) 0.0709(6) Uani 1 1 d . . . H4A H 0.2090 0.7999 0.7570 0.085 Uiso 1 1 calc R . . H4B H 0.1733 0.6935 0.6885 0.085 Uiso 1 1 calc R . . C41 C 0.3419(2) 0.8059(2) 0.68703(13) 0.0631(6) Uani 1 1 d . . . C42 C 0.4451(2) 0.89759(19) 0.72983(12) 0.0556(5) Uani 1 1 d . . . C43 C 0.5479(2) 0.94110(19) 0.69829(12) 0.0565(5) Uani 1 1 d . . . C44 C 0.5377(3) 0.8987(2) 0.61874(13) 0.0665(6) Uani 1 1 d . . . H44 H 0.6052 0.9273 0.5965 0.080 Uiso 1 1 calc R . . C45 C 0.4284(3) 0.8142(2) 0.57175(13) 0.0740(7) Uani 1 1 d . . . C46 C 0.3354(3) 0.7679(2) 0.60811(15) 0.0734(7) Uani 1 1 d . . . H46 H 0.2654 0.7085 0.5782 0.088 Uiso 1 1 calc R . . C47 C 0.4139(4) 0.7703(3) 0.48284(16) 0.1012(11) Uani 1 1 d . . . C471 C 0.5313(7) 0.8326(5) 0.4556(2) 0.165(2) Uani 1 1 d . . . H47A H 0.5307 0.9106 0.4644 0.247 Uiso 1 1 calc R . . H47B H 0.5186 0.8041 0.4001 0.247 Uiso 1 1 calc R . . H47C H 0.6171 0.8218 0.4854 0.247 Uiso 1 1 calc R . . C472 C 0.2884(7) 0.7986(7) 0.4360(2) 0.194(3) Uani 1 1 d . . . H47D H 0.2935 0.8771 0.4504 0.291 Uiso 1 1 calc R . . H47E H 0.2097 0.7591 0.4472 0.291 Uiso 1 1 calc R . . H47F H 0.2812 0.7777 0.3804 0.291 Uiso 1 1 calc R . . C473 C 0.4211(10) 0.6510(4) 0.4680(3) 0.210(4) Uani 1 1 d . . . H47G H 0.4131 0.6249 0.4127 0.315 Uiso 1 1 calc R . . H47H H 0.3479 0.6087 0.4823 0.315 Uiso 1 1 calc R . . H47I H 0.5069 0.6422 0.4993 0.315 Uiso 1 1 calc R . . O42 O 0.45137(16) 0.94404(14) 0.80784(9) 0.0636(4) Uani 1 1 d . . . C48 C 0.3638(3) 1.0185(3) 0.81627(17) 0.0813(7) Uani 1 1 d . . . H48A H 0.3840 1.0531 0.8721 0.098 Uiso 1 1 calc R . . H48B H 0.2705 0.9763 0.7997 0.098 Uiso 1 1 calc R . . C49 C 0.3736(4) 1.1054(3) 0.7714(2) 0.0916(9) Uani 1 1 d . . . N49 N 0.3785(5) 1.1726(3) 0.7360(3) 0.1475(15) 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 0.0619(12) 0.0533(12) 0.0680(12) 0.0212(10) 0.0197(10) 0.0154(10) C11 0.0489(10) 0.0440(11) 0.0662(12) 0.0136(9) 0.0137(8) 0.0068(8) C12 0.0499(10) 0.0487(11) 0.0629(11) 0.0122(9) 0.0186(8) 0.0075(8) C13 0.0468(10) 0.0455(11) 0.0732(13) 0.0128(9) 0.0174(9) 0.0093(8) C14 0.0557(11) 0.0535(12) 0.0674(12) 0.0178(9) 0.0154(9) 0.0152(9) C15 0.0489(10) 0.0536(12) 0.0616(11) 0.0113(9) 0.0135(8) 0.0098(9) C16 0.0494(10) 0.0465(11) 0.0695(12) 0.0106(9) 0.0143(9) 0.0124(9) N15 0.0655(11) 0.0734(13) 0.0666(11) 0.0149(10) 0.0177(9) 0.0229(10) O151 0.1091(15) 0.0930(14) 0.0772(11) 0.0123(10) 0.0318(10) 0.0476(12) O152 0.1409(19) 0.1184(18) 0.0783(12) 0.0435(12) 0.0408(12) 0.0687(16) O12 0.0713(9) 0.0709(11) 0.0695(9) 0.0204(8) 0.0285(7) 0.0190(8) C17 0.091(2) 0.124(3) 0.118(2) 0.049(2) 0.0583(18) 0.023(2) C18 0.240(7) 0.241(8) 0.163(5) 0.030(5) 0.139(5) -0.040(6) C19 0.46(2) 0.54(3) 0.202(9) 0.126(12) 0.160(11) -0.131(18) C2 0.0532(11) 0.0551(13) 0.0833(14) 0.0177(11) 0.0249(10) 0.0165(10) C21 0.0612(11) 0.0497(12) 0.0657(12) 0.0124(9) 0.0235(9) 0.0196(9) C22 0.0605(11) 0.0477(11) 0.0643(12) 0.0122(9) 0.0202(9) 0.0200(9) C23 0.0679(13) 0.0451(12) 0.0719(13) 0.0099(9) 0.0181(10) 0.0151(10) C24 0.0816(15) 0.0444(12) 0.0797(15) 0.0157(10) 0.0224(12) 0.0164(11) C25 0.0787(15) 0.0508(13) 0.0665(13) 0.0113(10) 0.0138(10) 0.0239(11) C26 0.0618(12) 0.0552(13) 0.0754(14) 0.0109(10) 0.0170(10) 0.0213(10) C27 0.0957(19) 0.0605(15) 0.0881(17) 0.0179(13) 0.0099(14) 0.0347(14) C271 0.226(6) 0.139(4) 0.141(3) 0.017(3) 0.043(3) 0.135(4) C272 0.156(4) 0.120(3) 0.178(4) 0.089(3) 0.024(3) 0.057(3) C273 0.103(3) 0.085(3) 0.303(7) 0.038(3) -0.058(4) 0.037(2) O22 0.0622(8) 0.0507(9) 0.0692(9) 0.0153(7) 0.0156(7) 0.0193(7) C28 0.0882(17) 0.0708(17) 0.0742(15) 0.0160(12) 0.0101(13) 0.0213(14) C29 0.136(3) 0.079(2) 0.0739(17) 0.0081(14) 0.0359(18) 0.0189(19) N29 0.175(4) 0.136(3) 0.123(3) -0.001(2) 0.084(3) 0.024(3) C3 0.0700(14) 0.0469(13) 0.1000(18) 0.0108(12) 0.0159(12) 0.0077(11) C31 0.0528(11) 0.0486(12) 0.0948(17) 0.0170(11) 0.0185(11) 0.0045(9) C32 0.0499(11) 0.0559(13) 0.0805(15) 0.0112(11) 0.0117(10) 0.0004(10) C33 0.0442(10) 0.0607(14) 0.0881(16) 0.0211(11) 0.0176(10) 0.0069(9) C34 0.0556(12) 0.0647(15) 0.0876(16) 0.0219(12) 0.0239(11) 0.0165(11) C35 0.0659(13) 0.0690(16) 0.0805(15) 0.0222(12) 0.0234(11) 0.0175(12) C36 0.0619(13) 0.0642(15) 0.0897(17) 0.0286(12) 0.0200(11) 0.0159(11) N35 0.1041(18) 0.106(2) 0.0849(16) 0.0270(14) 0.0272(13) 0.0463(16) O351 0.205(3) 0.173(3) 0.0912(16) 0.0427(17) 0.0287(17) 0.108(3) O352 0.223(4) 0.174(3) 0.0957(17) 0.0099(17) 0.0275(19) 0.132(3) O32 0.0748(11) 0.0709(12) 0.0883(12) 0.0005(9) 0.0003(9) 0.0056(9) C37 0.132(4) 0.136(4) 0.188(5) -0.035(4) -0.028(4) -0.054(3) C38 0.195(8) 0.264(12) 0.317(12) -0.096(9) 0.029(8) -0.116(8) C39 0.200(12) 0.121(9) 0.210(13) -0.050(8) 0.040(9) -0.031(8) C39' 0.092(7) 0.266(18) 0.187(12) 0.002(11) -0.040(7) -0.001(8) C4 0.0485(11) 0.0733(16) 0.0857(16) 0.0209(12) 0.0076(10) 0.0100(11) C41 0.0538(11) 0.0659(14) 0.0666(13) 0.0174(10) 0.0054(9) 0.0173(10) C42 0.0551(11) 0.0608(13) 0.0520(10) 0.0152(9) 0.0100(8) 0.0192(10) C43 0.0619(11) 0.0558(12) 0.0551(11) 0.0186(9) 0.0127(9) 0.0198(10) C44 0.0838(15) 0.0662(14) 0.0582(12) 0.0217(10) 0.0219(11) 0.0277(12) C45 0.0992(18) 0.0703(16) 0.0527(12) 0.0141(11) 0.0114(12) 0.0315(14) C46 0.0749(15) 0.0678(15) 0.0658(14) 0.0114(11) -0.0018(11) 0.0160(12) C47 0.152(3) 0.090(2) 0.0545(14) 0.0119(13) 0.0148(16) 0.028(2) C471 0.248(6) 0.172(5) 0.081(2) 0.010(3) 0.082(3) 0.026(5) C472 0.205(6) 0.286(8) 0.070(2) 0.031(3) -0.017(3) 0.081(6) C473 0.453(12) 0.100(3) 0.084(2) -0.003(2) 0.093(4) 0.068(5) O42 0.0633(8) 0.0734(11) 0.0550(8) 0.0133(7) 0.0170(6) 0.0159(8) C48 0.0823(16) 0.0845(19) 0.0819(16) 0.0103(14) 0.0324(13) 0.0244(14) C49 0.106(2) 0.0749(19) 0.099(2) 0.0104(16) 0.0314(17) 0.0359(17) N49 0.211(4) 0.103(3) 0.164(3) 0.054(2) 0.072(3) 0.074(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 C11 1.517(3) . ? C1 C43 1.518(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C11 C16 1.381(3) . ? C11 C12 1.402(3) . ? C12 O12 1.376(3) . ? C12 C13 1.399(3) . ? C13 C14 1.375(3) . ? C13 C2 1.519(3) . ? C14 C15 1.379(3) . ? C14 H14 0.9300 . ? C15 C16 1.381(3) . ? C15 N15 1.463(3) . ? C16 H16 0.9300 . ? N15 O152 1.210(3) . ? N15 O151 1.217(3) . ? O12 C17 1.437(4) . ? C17 C18 1.391(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.125(10) . ? C18 H18 0.9300 . ? C19 H19A 0.9300 . ? C19 H19B 0.9300 . ? C2 C21 1.507(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C21 C22 1.392(3) . ? C21 C26 1.394(3) . ? C22 C23 1.397(3) . ? C22 O22 1.397(2) . ? C23 C24 1.392(3) . ? C23 C3 1.520(4) . ? C24 C25 1.392(4) . ? C24 H24 0.9300 . ? C25 C26 1.387(3) . ? C25 C27 1.533(3) . ? C26 H26 0.9300 . ? C27 C273 1.484(5) . ? C27 C271 1.517(5) . ? C27 C272 1.518(6) . ? C271 H27A 0.9600 . ? C271 H27B 0.9600 . ? C271 H27C 0.9600 . ? C272 H27D 0.9600 . ? C272 H27E 0.9600 . ? C272 H27F 0.9600 . ? C273 H27G 0.9600 . ? C273 H27H 0.9600 . ? C273 H27I 0.9600 . ? O22 C28 1.412(3) . ? C28 C29 1.464(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N29 1.142(5) . ? C3 C31 1.517(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C31 C36 1.387(4) . ? C31 C32 1.397(3) . ? C32 O32 1.376(3) . ? C32 C33 1.388(3) . ? C33 C34 1.387(4) . ? C33 C4 1.521(3) . ? C34 C35 1.385(3) . ? C34 H34 0.9300 . ? C35 C36 1.380(4) . ? C35 N35 1.468(4) . ? C36 H36 0.9300 . ? N35 O352 1.197(4) . ? N35 O351 1.207(3) . ? O32 C37 1.450(5) . ? C37 C38 1.073(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.439(16) . ? C38 C39' 1.480(16) . ? C38 H38 0.9300 . ? C38 H38' 0.9300 . ? C39 H39A 0.9300 . ? C39 H39B 0.9300 . ? C39' H39C 0.9300 . ? C39' H39D 0.9300 . ? C4 C41 1.521(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C41 C46 1.384(4) . ? C41 C42 1.397(3) . ? C42 C43 1.390(3) . ? C42 O42 1.391(3) . ? C43 C44 1.395(3) . ? C44 C45 1.397(4) . ? C44 H44 0.9300 . ? C45 C46 1.384(4) . ? C45 C47 1.545(4) . ? C46 H46 0.9300 . ? C47 C473 1.484(6) . ? C47 C472 1.490(6) . ? C47 C471 1.551(7) . ? C471 H47A 0.9600 . ? C471 H47B 0.9600 . ? C471 H47C 0.9600 . ? C472 H47D 0.9600 . ? C472 H47E 0.9600 . ? C472 H47F 0.9600 . ? C473 H47G 0.9600 . ? C473 H47H 0.9600 . ? C473 H47I 0.9600 . ? O42 C48 1.409(3) . ? C48 C49 1.453(5) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 N49 1.131(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 C11 C1 C43 110.46(17) . . ? C11 C1 H1A 109.6 . . ? C43 C1 H1A 109.6 . . ? C11 C1 H1B 109.6 . . ? C43 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C16 C11 C12 118.22(18) . . ? C16 C11 C1 121.58(18) . . ? C12 C11 C1 120.01(19) . . ? O12 C12 C13 119.42(18) . . ? O12 C12 C11 118.26(18) . . ? C13 C12 C11 122.22(19) . . ? C14 C13 C12 117.92(19) . . ? C14 C13 C2 120.44(19) . . ? C12 C13 C2 121.6(2) . . ? C13 C14 C15 119.87(19) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 122.3(2) . . ? C14 C15 N15 119.26(19) . . ? C16 C15 N15 118.40(19) . . ? C11 C16 C15 119.14(19) . . ? C11 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? O152 N15 O151 122.3(2) . . ? O152 N15 C15 119.0(2) . . ? O151 N15 C15 118.7(2) . . ? C12 O12 C17 112.5(2) . . ? C18 C17 O12 112.3(4) . . ? C18 C17 H17A 109.1 . . ? O12 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? O12 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 133.5(11) . . ? C19 C18 H18 113.2 . . ? C17 C18 H18 113.2 . . ? C18 C19 H19A 120.0 . . ? C18 C19 H19B 120.0 . . ? H19A C19 H19B 120.0 . . ? C21 C2 C13 114.55(18) . . ? C21 C2 H2A 108.6 . . ? C13 C2 H2A 108.6 . . ? C21 C2 H2B 108.6 . . ? C13 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C22 C21 C26 117.7(2) . . ? C22 C21 C2 121.74(18) . . ? C26 C21 C2 120.5(2) . . ? C21 C22 C23 122.19(19) . . ? C21 C22 O22 117.69(19) . . ? C23 C22 O22 120.06(19) . . ? C24 C23 C22 116.6(2) . . ? C24 C23 C3 121.1(2) . . ? C22 C23 C3 122.30(19) . . ? C23 C24 C25 123.4(2) . . ? C23 C24 H24 118.3 . . ? C25 C24 H24 118.3 . . ? C26 C25 C24 117.0(2) . . ? C26 C25 C27 121.9(2) . . ? C24 C25 C27 121.1(2) . . ? C25 C26 C21 122.4(2) . . ? C25 C26 H26 118.8 . . ? C21 C26 H26 118.8 . . ? C273 C27 C271 113.7(4) . . ? C273 C27 C272 107.6(4) . . ? C271 C27 C272 104.7(4) . . ? C273 C27 C25 113.1(3) . . ? C271 C27 C25 107.3(2) . . ? C272 C27 C25 110.2(3) . . ? C27 C271 H27A 109.5 . . ? C27 C271 H27B 109.5 . . ? H27A C271 H27B 109.5 . . ? C27 C271 H27C 109.5 . . ? H27A C271 H27C 109.5 . . ? H27B C271 H27C 109.5 . . ? C27 C272 H27D 109.5 . . ? C27 C272 H27E 109.5 . . ? H27D C272 H27E 109.5 . . ? C27 C272 H27F 109.5 . . ? H27D C272 H27F 109.5 . . ? H27E C272 H27F 109.5 . . ? C27 C273 H27G 109.5 . . ? C27 C273 H27H 109.5 . . ? H27G C273 H27H 109.5 . . ? C27 C273 H27I 109.5 . . ? H27G C273 H27I 109.5 . . ? H27H C273 H27I 109.5 . . ? C22 O22 C28 114.56(17) . . ? O22 C28 C29 113.1(2) . . ? O22 C28 H28A 108.9 . . ? C29 C28 H28A 108.9 . . ? O22 C28 H28B 108.9 . . ? C29 C28 H28B 108.9 . . ? H28A C28 H28B 107.8 . . ? N29 C29 C28 178.0(4) . . ? C31 C3 C23 112.7(2) . . ? C31 C3 H3A 109.1 . . ? C23 C3 H3A 109.1 . . ? C31 C3 H3B 109.1 . . ? C23 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C36 C31 C32 117.8(2) . . ? C36 C31 C3 120.2(2) . . ? C32 C31 C3 122.0(2) . . ? O32 C32 C33 118.0(2) . . ? O32 C32 C31 119.0(2) . . ? C33 C32 C31 122.9(2) . . ? C34 C33 C32 118.1(2) . . ? C34 C33 C4 120.4(2) . . ? C32 C33 C4 121.3(2) . . ? C35 C34 C33 119.0(2) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C36 C35 C34 122.7(2) . . ? C36 C35 N35 118.8(2) . . ? C34 C35 N35 118.6(2) . . ? C35 C36 C31 119.2(2) . . ? C35 C36 H36 120.4 . . ? C31 C36 H36 120.4 . . ? O352 N35 O351 121.6(3) . . ? O352 N35 C35 119.3(3) . . ? O351 N35 C35 119.0(3) . . ? C32 O32 C37 111.6(3) . . ? C38 C37 O32 126.5(9) . . ? C38 C37 H37A 105.7 . . ? O32 C37 H37A 105.7 . . ? C38 C37 H37B 105.7 . . ? O32 C37 H37B 105.7 . . ? H37A C37 H37B 106.1 . . ? C37 C38 C39 127.8(15) . . ? C37 C38 C39' 123.8(13) . . ? C39 C38 C39' 96.5(10) . . ? C37 C38 H38 116.1 . . ? C39 C38 H38 116.1 . . ? C39' C38 H38 40.4 . . ? C37 C38 H38' 118.1 . . ? C39 C38 H38' 39.5 . . ? C39' C38 H38' 118.1 . . ? H38 C38 H38' 109.9 . . ? C38 C39 H39A 120.0 . . ? C38 C39 H39B 120.0 . . ? H39A C39 H39B 120.0 . . ? C38 C39' H39C 120.0 . . ? C38 C39' H39D 120.0 . . ? H39C C39' H39D 120.0 . . ? C33 C4 C41 110.77(18) . . ? C33 C4 H4A 109.5 . . ? C41 C4 H4A 109.5 . . ? C33 C4 H4B 109.5 . . ? C41 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C46 C41 C42 117.4(2) . . ? C46 C41 C4 121.9(2) . . ? C42 C41 C4 120.6(2) . . ? C43 C42 O42 118.07(19) . . ? C43 C42 C41 121.9(2) . . ? O42 C42 C41 120.0(2) . . ? C42 C43 C44 118.1(2) . . ? C42 C43 C1 120.16(19) . . ? C44 C43 C1 121.7(2) . . ? C43 C44 C45 121.4(2) . . ? C43 C44 H44 119.3 . . ? C45 C44 H44 119.3 . . ? C46 C45 C44 117.8(2) . . ? C46 C45 C47 120.6(3) . . ? C44 C45 C47 121.6(3) . . ? C41 C46 C45 122.9(2) . . ? C41 C46 H46 118.6 . . ? C45 C46 H46 118.6 . . ? C473 C47 C472 116.1(5) . . ? C473 C47 C45 110.3(3) . . ? C472 C47 C45 107.9(3) . . ? C473 C47 C471 106.7(5) . . ? C472 C47 C471 104.3(4) . . ? C45 C47 C471 111.6(3) . . ? C47 C471 H47A 109.5 . . ? C47 C471 H47B 109.5 . . ? H47A C471 H47B 109.5 . . ? C47 C471 H47C 109.5 . . ? H47A C471 H47C 109.5 . . ? H47B C471 H47C 109.5 . . ? C47 C472 H47D 109.5 . . ? C47 C472 H47E 109.5 . . ? H47D C472 H47E 109.5 . . ? C47 C472 H47F 109.5 . . ? H47D C472 H47F 109.5 . . ? H47E C472 H47F 109.5 . . ? C47 C473 H47G 109.5 . . ? C47 C473 H47H 109.5 . . ? H47G C473 H47H 109.5 . . ? C47 C473 H47I 109.5 . . ? H47G C473 H47I 109.5 . . ? H47H C473 H47I 109.5 . . ? C42 O42 C48 114.98(17) . . ? O42 C48 C49 114.8(2) . . ? O42 C48 H48A 108.6 . . ? C49 C48 H48A 108.6 . . ? O42 C48 H48B 108.6 . . ? C49 C48 H48B 108.6 . . ? H48A C48 H48B 107.5 . . ? N49 C49 C48 178.7(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 C43 C1 C11 C16 -104.0(2) . . . . ? C43 C1 C11 C12 70.8(3) . . . . ? C16 C11 C12 O12 -177.70(19) . . . . ? C1 C11 C12 O12 7.3(3) . . . . ? C16 C11 C12 C13 6.1(3) . . . . ? C1 C11 C12 C13 -168.9(2) . . . . ? O12 C12 C13 C14 179.87(19) . . . . ? C11 C12 C13 C14 -3.9(3) . . . . ? O12 C12 C13 C2 -2.4(3) . . . . ? C11 C12 C13 C2 173.8(2) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C2 C13 C14 C15 -178.8(2) . . . . ? C13 C14 C15 C16 3.8(3) . . . . ? C13 C14 C15 N15 -177.14(19) . . . . ? C12 C11 C16 C15 -3.2(3) . . . . ? C1 C11 C16 C15 171.7(2) . . . . ? C14 C15 C16 C11 -1.6(3) . . . . ? N15 C15 C16 C11 179.34(19) . . . . ? C14 C15 N15 O152 -11.0(3) . . . . ? C16 C15 N15 O152 168.1(2) . . . . ? C14 C15 N15 O151 167.5(2) . . . . ? C16 C15 N15 O151 -13.4(3) . . . . ? C13 C12 O12 C17 -89.3(3) . . . . ? C11 C12 O12 C17 94.4(3) . . . . ? C12 O12 C17 C18 177.9(5) . . . . ? O12 C17 C18 C19 167.2(16) . . . . ? C14 C13 C2 C21 62.8(3) . . . . ? C12 C13 C2 C21 -114.9(2) . . . . ? C13 C2 C21 C22 46.1(3) . . . . ? C13 C2 C21 C26 -136.8(2) . . . . ? C26 C21 C22 C23 8.0(3) . . . . ? C2 C21 C22 C23 -174.8(2) . . . . ? C26 C21 C22 O22 -174.85(19) . . . . ? C2 C21 C22 O22 2.3(3) . . . . ? C21 C22 C23 C24 -7.9(3) . . . . ? O22 C22 C23 C24 175.0(2) . . . . ? C21 C22 C23 C3 172.2(2) . . . . ? O22 C22 C23 C3 -4.8(3) . . . . ? C22 C23 C24 C25 1.5(4) . . . . ? C3 C23 C24 C25 -178.6(2) . . . . ? C23 C24 C25 C26 4.3(4) . . . . ? C23 C24 C25 C27 -173.5(2) . . . . ? C24 C25 C26 C21 -4.2(4) . . . . ? C27 C25 C26 C21 173.6(2) . . . . ? C22 C21 C26 C25 -1.7(3) . . . . ? C2 C21 C26 C25 -178.9(2) . . . . ? C26 C25 C27 C273 23.4(5) . . . . ? C24 C25 C27 C273 -158.8(4) . . . . ? C26 C25 C27 C271 -102.8(4) . . . . ? C24 C25 C27 C271 75.0(4) . . . . ? C26 C25 C27 C272 143.8(3) . . . . ? C24 C25 C27 C272 -38.4(4) . . . . ? C21 C22 O22 C28 102.2(2) . . . . ? C23 C22 O22 C28 -80.6(3) . . . . ? C22 O22 C28 C29 -52.0(3) . . . . ? O22 C28 C29 N29 64(12) . . . . ? C24 C23 C3 C31 132.7(3) . . . . ? C22 C23 C3 C31 -47.4(3) . . . . ? C23 C3 C31 C36 -58.3(3) . . . . ? C23 C3 C31 C32 118.2(3) . . . . ? C36 C31 C32 O32 -176.8(2) . . . . ? C3 C31 C32 O32 6.6(3) . . . . ? C36 C31 C32 C33 7.4(4) . . . . ? C3 C31 C32 C33 -169.2(2) . . . . ? O32 C32 C33 C34 177.1(2) . . . . ? C31 C32 C33 C34 -7.1(3) . . . . ? O32 C32 C33 C4 -7.1(3) . . . . ? C31 C32 C33 C4 168.7(2) . . . . ? C32 C33 C34 C35 1.4(3) . . . . ? C4 C33 C34 C35 -174.5(2) . . . . ? C33 C34 C35 C36 3.8(4) . . . . ? C33 C34 C35 N35 -177.5(2) . . . . ? C34 C35 C36 C31 -3.5(4) . . . . ? N35 C35 C36 C31 177.9(2) . . . . ? C32 C31 C36 C35 -2.0(4) . . . . ? C3 C31 C36 C35 174.7(2) . . . . ? C36 C35 N35 O352 178.8(4) . . . . ? C34 C35 N35 O352 0.1(5) . . . . ? C36 C35 N35 O351 -3.8(5) . . . . ? C34 C35 N35 O351 177.5(3) . . . . ? C33 C32 O32 C37 -96.3(4) . . . . ? C31 C32 O32 C37 87.7(4) . . . . ? C32 O32 C37 C38 -178.1(11) . . . . ? O32 C37 C38 C39 118.1(14) . . . . ? O32 C37 C38 C39' -108.1(13) . . . . ? C34 C33 C4 C41 105.7(3) . . . . ? C32 C33 C4 C41 -70.0(3) . . . . ? C33 C4 C41 C46 106.6(2) . . . . ? C33 C4 C41 C42 -68.9(3) . . . . ? C46 C41 C42 C43 -7.8(3) . . . . ? C4 C41 C42 C43 167.88(19) . . . . ? C46 C41 C42 O42 175.83(18) . . . . ? C4 C41 C42 O42 -8.5(3) . . . . ? O42 C42 C43 C44 -176.53(18) . . . . ? C41 C42 C43 C44 7.0(3) . . . . ? O42 C42 C43 C1 6.5(3) . . . . ? C41 C42 C43 C1 -169.89(18) . . . . ? C11 C1 C43 C42 65.6(3) . . . . ? C11 C1 C43 C44 -111.3(2) . . . . ? C42 C43 C44 C45 -0.6(3) . . . . ? C1 C43 C44 C45 176.3(2) . . . . ? C43 C44 C45 C46 -4.7(3) . . . . ? C43 C44 C45 C47 177.6(2) . . . . ? C42 C41 C46 C45 2.2(3) . . . . ? C4 C41 C46 C45 -173.4(2) . . . . ? C44 C45 C46 C41 3.9(4) . . . . ? C47 C45 C46 C41 -178.4(2) . . . . ? C46 C45 C47 C473 -60.3(5) . . . . ? C44 C45 C47 C473 117.3(5) . . . . ? C46 C45 C47 C472 67.4(5) . . . . ? C44 C45 C47 C472 -115.0(4) . . . . ? C46 C45 C47 C471 -178.6(3) . . . . ? C44 C45 C47 C471 -1.0(5) . . . . ? C43 C42 O42 C48 101.5(2) . . . . ? C41 C42 O42 C48 -82.0(3) . . . . ? C42 O42 C48 C49 -51.2(3) . . . . ? O42 C48 C49 N49 135(16) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.91 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.469 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.045 data_boeh34 _database_code_depnum_ccdc_archive 'CCDC 272781' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H66 N2 O4' _chemical_formula_weight 807.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4041(19) _cell_length_b 10.6679(19) _cell_length_c 11.557(2) _cell_angle_alpha 105.672(14) _cell_angle_beta 91.147(15) _cell_angle_gamma 108.061(14) _cell_volume 1166.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20072 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 25.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14867 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.71 _reflns_number_total 4239 _reflns_number_gt 3565 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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 Rfactors 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^)+(0.1421P)^2^+4.4600P] 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 4239 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0983 _refine_ls_wR_factor_ref 0.3313 _refine_ls_wR_factor_gt 0.3160 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4382(6) 0.1125(6) 0.3461(6) 0.0197(13) Uani 1 1 d . . . H1A H 0.4661 0.0445 0.3751 0.024 Uiso 1 1 calc R . . H1B H 0.3861 0.0632 0.2653 0.024 Uiso 1 1 calc R . . C11 C 0.5667(6) 0.2208(6) 0.3304(6) 0.0167(12) Uani 1 1 d . . . C12 C 0.6447(6) 0.3355(6) 0.4250(5) 0.0156(12) Uani 1 1 d . . . C13 C 0.7591(6) 0.4336(6) 0.4061(5) 0.0147(12) Uani 1 1 d . . . C14 C 0.8007(6) 0.4137(6) 0.2902(6) 0.0199(13) Uani 1 1 d . . . H14 H 0.8815 0.4780 0.2773 0.024 Uiso 1 1 calc R . . C15 C 0.7257(6) 0.3001(6) 0.1913(6) 0.0198(13) Uani 1 1 d . . . C16 C 0.6091(6) 0.2076(6) 0.2148(6) 0.0175(12) Uani 1 1 d . . . H16 H 0.5559 0.1321 0.1495 0.021 Uiso 1 1 calc R . . O12 O 0.6015(4) 0.3586(4) 0.5421(4) 0.0177(9) Uani 1 1 d . . . C121 C 0.6223(7) 0.2704(7) 0.6088(6) 0.0231(14) Uani 1 1 d . . . H12A H 0.5937 0.1745 0.5552 0.028 Uiso 1 1 calc R . . H12B H 0.5646 0.2728 0.6759 0.028 Uiso 1 1 calc R . . C122 C 0.7647(7) 0.3112(7) 0.6582(6) 0.0266(14) Uani 1 1 d . . . N123 N 0.8763(7) 0.3407(8) 0.7000(7) 0.0448(18) Uani 1 1 d . . . C17 C 0.7743(7) 0.2876(7) 0.0655(6) 0.0264(14) Uani 1 1 d . . . C171 C 0.6818(12) 0.1673(12) -0.0296(7) 0.073(4) Uani 1 1 d . . . H17A H 0.7172 0.1643 -0.1079 0.110 Uiso 1 1 calc R . . H17B H 0.5909 0.1761 -0.0339 0.110 Uiso 1 1 calc R . . H17C H 0.6763 0.0823 -0.0097 0.110 Uiso 1 1 calc R . . C172 C 0.9198(10) 0.2782(12) 0.0702(9) 0.057(3) Uani 1 1 d . . . H17D H 0.9800 0.3580 0.1329 0.085 Uiso 1 1 calc R . . H17E H 0.9537 0.2770 -0.0084 0.085 Uiso 1 1 calc R . . H17F H 0.9177 0.1934 0.0892 0.085 Uiso 1 1 calc R . . C173 C 0.7891(11) 0.4249(10) 0.0347(8) 0.053(2) Uani 1 1 d . . . H17G H 0.8502 0.5026 0.0986 0.080 Uiso 1 1 calc R . . H17H H 0.6995 0.4364 0.0288 0.080 Uiso 1 1 calc R . . H17I H 0.8267 0.4219 -0.0427 0.080 Uiso 1 1 calc R . . C2 C 0.8358(5) 0.5646(6) 0.5059(6) 0.0159(12) Uani 1 1 d . . . H2A H 0.9345 0.5886 0.4983 0.019 Uiso 1 1 calc R . . H2B H 0.8211 0.5481 0.5856 0.019 Uiso 1 1 calc R . . C21 C 0.7889(6) 0.6850(6) 0.4994(5) 0.0147(11) Uani 1 1 d . . . C22 C 0.7054(5) 0.7328(6) 0.5796(5) 0.0140(11) Uani 1 1 d . . . C23 C 0.6579(6) 0.8387(5) 0.5687(5) 0.0157(12) Uani 1 1 d . . . C24 C 0.7019(6) 0.9011(6) 0.4799(5) 0.0176(12) Uani 1 1 d . . . H24 H 0.6713 0.9745 0.4738 0.021 Uiso 1 1 calc R . . C25 C 0.7905(6) 0.8607(6) 0.3978(6) 0.0185(12) Uani 1 1 d . . . C26 C 0.8307(6) 0.7508(6) 0.4093(6) 0.0190(12) Uani 1 1 d . . . H26 H 0.8884 0.7192 0.3544 0.023 Uiso 1 1 calc R . . O22 O 0.6552(4) 0.6651(4) 0.6650(4) 0.0189(9) Uani 1 1 d . . . C221 C 0.7388(9) 0.7230(8) 0.7805(6) 0.0341(17) Uani 1 1 d . . . H22A H 0.7422 0.8193 0.8175 0.041 Uiso 1 1 calc R . . H22B H 0.8327 0.7218 0.7703 0.041 Uiso 1 1 calc R . . C222 C 0.6731(11) 0.6339(9) 0.8587(8) 0.049(2) Uani 1 1 d . . . H222 H 0.7222 0.6513 0.9347 0.058 Uiso 1 1 calc R . . C223 C 0.5548(11) 0.5345(10) 0.8327(9) 0.051(2) Uani 1 1 d . . . H22C H 0.5015 0.5128 0.7579 0.061 Uiso 1 1 calc R . . H22D H 0.5227 0.4844 0.8889 0.061 Uiso 1 1 calc R . . C27 C 0.8327(7) 0.9312(7) 0.2986(6) 0.0258(14) Uani 1 1 d . . . C271 C 0.8699(8) 1.0860(7) 0.3483(7) 0.0329(16) Uani 1 1 d . . . H27A H 0.7939 1.1086 0.3875 0.049 Uiso 1 1 calc R . . H27B H 0.8890 1.1278 0.2821 0.049 Uiso 1 1 calc R . . H27C H 0.9508 1.1219 0.4077 0.049 Uiso 1 1 calc R . . C272 C 0.9510(13) 0.8963(13) 0.2394(12) 0.081(5) Uani 1 1 d . . . H27D H 0.9266 0.7961 0.2061 0.121 Uiso 1 1 calc R . . H27E H 1.0309 0.9309 0.2997 0.121 Uiso 1 1 calc R . . H27F H 0.9721 0.9393 0.1741 0.121 Uiso 1 1 calc R . . C273 C 0.7082(11) 0.8805(10) 0.2003(7) 0.054(3) Uani 1 1 d . . . H27G H 0.6312 0.9029 0.2375 0.081 Uiso 1 1 calc R . . H27H H 0.6828 0.7806 0.1646 0.081 Uiso 1 1 calc R . . H27I H 0.7323 0.9263 0.1370 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(3) 0.009(3) 0.027(3) 0.004(2) 0.011(3) 0.004(2) C11 0.017(3) 0.013(3) 0.023(3) 0.006(2) 0.005(2) 0.009(2) C12 0.017(3) 0.014(3) 0.020(3) 0.004(2) 0.007(2) 0.011(2) C13 0.012(3) 0.012(3) 0.021(3) 0.007(2) 0.000(2) 0.003(2) C14 0.021(3) 0.018(3) 0.024(3) 0.010(3) 0.008(3) 0.007(2) C15 0.022(3) 0.022(3) 0.021(3) 0.011(2) 0.007(2) 0.009(3) C16 0.019(3) 0.015(3) 0.020(3) 0.006(2) 0.004(2) 0.007(2) O12 0.020(2) 0.014(2) 0.018(2) 0.0049(16) 0.0064(17) 0.0052(16) C121 0.027(3) 0.020(3) 0.021(3) 0.010(3) 0.007(3) 0.002(3) C122 0.030(4) 0.033(4) 0.021(3) 0.013(3) 0.008(3) 0.013(3) N123 0.036(4) 0.064(5) 0.047(4) 0.029(4) 0.006(3) 0.024(3) C17 0.032(4) 0.028(4) 0.019(3) 0.010(3) 0.011(3) 0.007(3) C171 0.076(7) 0.079(8) 0.015(4) -0.007(4) 0.011(4) -0.026(6) C172 0.060(6) 0.079(7) 0.045(5) 0.021(5) 0.028(5) 0.037(5) C173 0.077(7) 0.058(6) 0.034(5) 0.030(4) 0.016(4) 0.021(5) C2 0.012(3) 0.014(3) 0.022(3) 0.005(2) 0.001(2) 0.005(2) C21 0.010(2) 0.013(3) 0.022(3) 0.007(2) 0.000(2) 0.004(2) C22 0.011(3) 0.014(3) 0.011(3) 0.003(2) -0.001(2) -0.003(2) C23 0.012(3) 0.006(2) 0.022(3) 0.000(2) 0.004(2) -0.003(2) C24 0.021(3) 0.014(3) 0.021(3) 0.007(2) 0.005(2) 0.009(2) C25 0.018(3) 0.016(3) 0.023(3) 0.009(2) 0.005(2) 0.005(2) C26 0.018(3) 0.017(3) 0.024(3) 0.009(2) 0.008(2) 0.006(2) O22 0.022(2) 0.018(2) 0.015(2) 0.0075(17) -0.0004(17) 0.0028(17) C221 0.047(4) 0.035(4) 0.012(3) 0.002(3) -0.007(3) 0.008(3) C222 0.089(7) 0.049(5) 0.025(4) 0.019(4) 0.016(4) 0.038(5) C223 0.071(6) 0.060(6) 0.046(5) 0.040(5) 0.030(5) 0.032(5) C27 0.029(3) 0.027(3) 0.028(3) 0.014(3) 0.013(3) 0.013(3) C271 0.038(4) 0.021(3) 0.039(4) 0.017(3) 0.005(3) 0.001(3) C272 0.107(9) 0.106(9) 0.112(9) 0.094(8) 0.096(8) 0.091(8) C273 0.073(6) 0.045(5) 0.024(4) 0.015(4) -0.007(4) -0.014(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 C11 1.523(8) . ? C1 C23 1.525(8) 2_666 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C11 C16 1.400(9) . ? C11 C12 1.406(8) . ? C12 C13 1.385(8) . ? C12 O12 1.416(7) . ? C13 C14 1.398(9) . ? C13 C2 1.524(8) . ? C14 C15 1.419(9) . ? C14 H14 0.9500 . ? C15 C16 1.392(8) . ? C15 C17 1.534(8) . ? C16 H16 0.9500 . ? O12 C121 1.428(8) . ? C121 C122 1.464(10) . ? C121 H12A 0.9900 . ? C121 H12B 0.9900 . ? C122 N123 1.162(10) . ? C17 C171 1.487(11) . ? C17 C172 1.548(12) . ? C17 C173 1.563(11) . ? C171 H17A 0.9800 . ? C171 H17B 0.9800 . ? C171 H17C 0.9800 . ? C172 H17D 0.9800 . ? C172 H17E 0.9800 . ? C172 H17F 0.9800 . ? C173 H17G 0.9800 . ? C173 H17H 0.9800 . ? C173 H17I 0.9800 . ? C2 C21 1.527(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C21 C22 1.387(8) . ? C21 C26 1.410(8) . ? C22 O22 1.393(7) . ? C22 C23 1.398(8) . ? C23 C24 1.381(8) . ? C23 C1 1.525(8) 2_666 ? C24 C25 1.413(8) . ? C24 H24 0.9500 . ? C25 C26 1.398(8) . ? C25 C27 1.533(8) . ? C26 H26 0.9500 . ? O22 C221 1.447(8) . ? C221 C222 1.508(11) . ? C221 H22A 0.9900 . ? C221 H22B 0.9900 . ? C222 C223 1.316(14) . ? C222 H222 0.9500 . ? C223 H22C 0.9500 . ? C223 H22D 0.9500 . ? C27 C271 1.513(9) . ? C27 C272 1.518(10) . ? C27 C273 1.561(11) . ? C271 H27A 0.9800 . ? C271 H27B 0.9800 . ? C271 H27C 0.9800 . ? C272 H27D 0.9800 . ? C272 H27E 0.9800 . ? C272 H27F 0.9800 . ? C273 H27G 0.9800 . ? C273 H27H 0.9800 . ? C273 H27I 0.9800 . ? 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 C11 C1 C23 117.8(5) . 2_666 ? C11 C1 H1A 107.9 . . ? C23 C1 H1A 107.9 2_666 . ? C11 C1 H1B 107.9 . . ? C23 C1 H1B 107.9 2_666 . ? H1A C1 H1B 107.2 . . ? C16 C11 C12 117.6(5) . . ? C16 C11 C1 118.5(6) . . ? C12 C11 C1 123.9(5) . . ? C13 C12 C11 122.1(5) . . ? C13 C12 O12 117.9(5) . . ? C11 C12 O12 119.9(5) . . ? C12 C13 C14 118.5(5) . . ? C12 C13 C2 122.0(5) . . ? C14 C13 C2 119.4(5) . . ? C13 C14 C15 121.9(5) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 117.0(5) . . ? C16 C15 C17 123.8(6) . . ? C14 C15 C17 119.1(5) . . ? C15 C16 C11 122.9(6) . . ? C15 C16 H16 118.6 . . ? C11 C16 H16 118.6 . . ? C12 O12 C121 115.2(4) . . ? O12 C121 C122 112.0(5) . . ? O12 C121 H12A 109.2 . . ? C122 C121 H12A 109.2 . . ? O12 C121 H12B 109.2 . . ? C122 C121 H12B 109.2 . . ? H12A C121 H12B 107.9 . . ? N123 C122 C121 177.6(7) . . ? C171 C17 C15 112.8(6) . . ? C171 C17 C172 110.1(8) . . ? C15 C17 C172 109.3(6) . . ? C171 C17 C173 110.9(8) . . ? C15 C17 C173 108.1(6) . . ? C172 C17 C173 105.3(7) . . ? C17 C171 H17A 109.5 . . ? C17 C171 H17B 109.5 . . ? H17A C171 H17B 109.5 . . ? C17 C171 H17C 109.5 . . ? H17A C171 H17C 109.5 . . ? H17B C171 H17C 109.5 . . ? C17 C172 H17D 109.5 . . ? C17 C172 H17E 109.5 . . ? H17D C172 H17E 109.5 . . ? C17 C172 H17F 109.5 . . ? H17D C172 H17F 109.5 . . ? H17E C172 H17F 109.5 . . ? C17 C173 H17G 109.5 . . ? C17 C173 H17H 109.5 . . ? H17G C173 H17H 109.5 . . ? C17 C173 H17I 109.5 . . ? H17G C173 H17I 109.5 . . ? H17H C173 H17I 109.5 . . ? C13 C2 C21 111.5(5) . . ? C13 C2 H2A 109.3 . . ? C21 C2 H2A 109.3 . . ? C13 C2 H2B 109.3 . . ? C21 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C22 C21 C26 118.1(5) . . ? C22 C21 C2 122.2(5) . . ? C26 C21 C2 119.7(5) . . ? C21 C22 O22 119.8(5) . . ? C21 C22 C23 121.5(5) . . ? O22 C22 C23 118.4(5) . . ? C24 C23 C22 118.6(5) . . ? C24 C23 C1 119.9(5) . 2_666 ? C22 C23 C1 121.5(5) . 2_666 ? C23 C24 C25 122.9(5) . . ? C23 C24 H24 118.6 . . ? C25 C24 H24 118.6 . . ? C26 C25 C24 116.3(5) . . ? C26 C25 C27 123.1(6) . . ? C24 C25 C27 120.6(5) . . ? C25 C26 C21 122.6(6) . . ? C25 C26 H26 118.7 . . ? C21 C26 H26 118.7 . . ? C22 O22 C221 113.6(5) . . ? O22 C221 C222 106.2(6) . . ? O22 C221 H22A 110.5 . . ? C222 C221 H22A 110.5 . . ? O22 C221 H22B 110.5 . . ? C222 C221 H22B 110.5 . . ? H22A C221 H22B 108.7 . . ? C223 C222 C221 126.8(8) . . ? C223 C222 H222 116.6 . . ? C221 C222 H222 116.6 . . ? C222 C223 H22C 120.0 . . ? C222 C223 H22D 120.0 . . ? H22C C223 H22D 120.0 . . ? C271 C27 C272 109.4(7) . . ? C271 C27 C25 111.1(6) . . ? C272 C27 C25 111.9(6) . . ? C271 C27 C273 107.3(6) . . ? C272 C27 C273 108.8(8) . . ? C25 C27 C273 108.1(6) . . ? C27 C271 H27A 109.5 . . ? C27 C271 H27B 109.5 . . ? H27A C271 H27B 109.5 . . ? C27 C271 H27C 109.5 . . ? H27A C271 H27C 109.5 . . ? H27B C271 H27C 109.5 . . ? C27 C272 H27D 109.5 . . ? C27 C272 H27E 109.5 . . ? H27D C272 H27E 109.5 . . ? C27 C272 H27F 109.5 . . ? H27D C272 H27F 109.5 . . ? H27E C272 H27F 109.5 . . ? C27 C273 H27G 109.5 . . ? C27 C273 H27H 109.5 . . ? H27G C273 H27H 109.5 . . ? C27 C273 H27I 109.5 . . ? H27G C273 H27I 109.5 . . ? H27H C273 H27I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 C1 C11 C16 -140.4(6) 2_666 . . . ? C23 C1 C11 C12 38.4(8) 2_666 . . . ? C16 C11 C12 C13 0.5(8) . . . . ? C1 C11 C12 C13 -178.3(5) . . . . ? C16 C11 C12 O12 175.9(5) . . . . ? C1 C11 C12 O12 -2.9(8) . . . . ? C11 C12 C13 C14 -2.9(8) . . . . ? O12 C12 C13 C14 -178.4(5) . . . . ? C11 C12 C13 C2 174.1(5) . . . . ? O12 C12 C13 C2 -1.4(8) . . . . ? C12 C13 C14 C15 3.1(8) . . . . ? C2 C13 C14 C15 -174.0(5) . . . . ? C13 C14 C15 C16 -0.9(9) . . . . ? C13 C14 C15 C17 177.7(6) . . . . ? C14 C15 C16 C11 -1.6(9) . . . . ? C17 C15 C16 C11 179.8(6) . . . . ? C12 C11 C16 C15 1.8(8) . . . . ? C1 C11 C16 C15 -179.3(5) . . . . ? C13 C12 O12 C121 -109.0(6) . . . . ? C11 C12 O12 C121 75.3(7) . . . . ? C12 O12 C121 C122 76.7(6) . . . . ? O12 C121 C122 N123 166(20) . . . . ? C16 C15 C17 C171 1.3(11) . . . . ? C14 C15 C17 C171 -177.2(8) . . . . ? C16 C15 C17 C172 -121.6(7) . . . . ? C14 C15 C17 C172 59.9(8) . . . . ? C16 C15 C17 C173 124.3(7) . . . . ? C14 C15 C17 C173 -54.2(8) . . . . ? C12 C13 C2 C21 -95.1(6) . . . . ? C14 C13 C2 C21 81.9(6) . . . . ? C13 C2 C21 C22 104.6(6) . . . . ? C13 C2 C21 C26 -75.2(6) . . . . ? C26 C21 C22 O22 176.1(5) . . . . ? C2 C21 C22 O22 -3.8(8) . . . . ? C26 C21 C22 C23 3.0(8) . . . . ? C2 C21 C22 C23 -176.8(5) . . . . ? C21 C22 C23 C24 -3.6(8) . . . . ? O22 C22 C23 C24 -176.7(5) . . . . ? C21 C22 C23 C1 177.6(5) . . . 2_666 ? O22 C22 C23 C1 4.5(8) . . . 2_666 ? C22 C23 C24 C25 1.4(9) . . . . ? C1 C23 C24 C25 -179.7(6) 2_666 . . . ? C23 C24 C25 C26 1.0(9) . . . . ? C23 C24 C25 C27 178.2(6) . . . . ? C24 C25 C26 C21 -1.5(9) . . . . ? C27 C25 C26 C21 -178.7(6) . . . . ? C22 C21 C26 C25 -0.4(9) . . . . ? C2 C21 C26 C25 179.5(6) . . . . ? C21 C22 O22 C221 93.4(7) . . . . ? C23 C22 O22 C221 -93.4(6) . . . . ? C22 O22 C221 C222 -177.5(6) . . . . ? O22 C221 C222 C223 -7.7(12) . . . . ? C26 C25 C27 C271 -138.5(7) . . . . ? C24 C25 C27 C271 44.4(8) . . . . ? C26 C25 C27 C272 -15.9(11) . . . . ? C24 C25 C27 C272 167.1(8) . . . . ? C26 C25 C27 C273 103.9(8) . . . . ? C24 C25 C27 C273 -73.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.584 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.125