# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_klien_16_0m _database_code_depnum_ccdc_archive 'CCDC 900658' #TrackingRef 'Klien16fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H62 O2, 2(C3 H8 O)' _chemical_formula_sum 'C66 H78 O4' _chemical_formula_weight 935.28 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7197(2) _cell_length_b 11.1072(2) _cell_length_c 13.5033(3) _cell_angle_alpha 66.951(1) _cell_angle_beta 68.682(1) _cell_angle_gamma 85.301(1) _cell_volume 1374.78(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7006 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 29.08 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.068 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 27270 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 29.17 _reflns_number_total 7345 _reflns_number_gt 5560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.3546P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7345 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O1 O 0.86940(8) -0.01716(8) 0.43628(7) 0.01606(18) Uani 1 1 d . . . H1 H 0.9034 0.0506 0.4327 0.024 Uiso 1 1 calc R . . C1 C 1.06389(11) -0.01075(11) 0.26769(10) 0.0138(2) Uani 1 1 d . . . C2 C 1.15010(11) -0.10041(11) 0.30643(10) 0.0158(2) Uani 1 1 d . . . H2 H 1.1153 -0.1787 0.3732 0.019 Uiso 1 1 calc R . . C3 C 1.28880(11) -0.07526(11) 0.24691(11) 0.0163(2) Uani 1 1 d . . . C4 C 1.33503(12) 0.04008(12) 0.14723(11) 0.0189(3) Uani 1 1 d . . . H4 H 1.4289 0.0572 0.1049 0.023 Uiso 1 1 calc R . . C5 C 1.24861(12) 0.13010(12) 0.10820(11) 0.0176(2) Uani 1 1 d . . . H5 H 1.2826 0.2077 0.0406 0.021 Uiso 1 1 calc R . . C6 C 1.11174(11) 0.10450(11) 0.16981(10) 0.0142(2) Uani 1 1 d . . . C7 C 0.99705(11) 0.17910(11) 0.15161(10) 0.0142(2) Uani 1 1 d . . . C8 C 0.99017(12) 0.29757(11) 0.06622(10) 0.0165(2) Uani 1 1 d . . . H8 H 1.0693 0.3440 0.0044 0.020 Uiso 1 1 calc R . . C9 C 0.86541(12) 0.34707(12) 0.07273(11) 0.0179(2) Uani 1 1 d . . . H9 H 0.8605 0.4276 0.0138 0.022 Uiso 1 1 calc R . . C10 C 0.74666(12) 0.28228(11) 0.16327(10) 0.0158(2) Uani 1 1 d . . . C11 C 0.75526(11) 0.16161(11) 0.24742(10) 0.0155(2) Uani 1 1 d . . . H11 H 0.6764 0.1148 0.3094 0.019 Uiso 1 1 calc R . . C12 C 0.87897(11) 0.11093(11) 0.23989(10) 0.0138(2) Uani 1 1 d . . . C13 C 0.91048(11) -0.01713(11) 0.32248(10) 0.0131(2) Uani 1 1 d . . . C14 C 0.84276(11) -0.14113(11) 0.33441(10) 0.0135(2) Uani 1 1 d . . . C15 C 0.76404(11) -0.22872(12) 0.44378(10) 0.0163(2) Uani 1 1 d . . . H15 H 0.7491 -0.2079 0.5088 0.020 Uiso 1 1 calc R . . C16 C 0.70692(12) -0.34583(12) 0.45970(11) 0.0188(3) Uani 1 1 d . . . H16 H 0.6540 -0.4043 0.5351 0.023 Uiso 1 1 calc R . . C17 C 0.72693(12) -0.37735(12) 0.36604(11) 0.0196(3) Uani 1 1 d . . . H17 H 0.6898 -0.4582 0.3766 0.024 Uiso 1 1 calc R . . C18 C 0.80196(12) -0.28938(12) 0.25630(11) 0.0186(3) Uani 1 1 d . . . H18 H 0.8142 -0.3103 0.1917 0.022 Uiso 1 1 calc R . . C19 C 0.85983(11) -0.17106(11) 0.23844(10) 0.0144(2) Uani 1 1 d . . . C20 C 0.93386(11) -0.08170(11) 0.11613(10) 0.0142(2) Uani 1 1 d . . . C21 C 1.07083(11) -0.08824(11) 0.06146(10) 0.0158(2) Uani 1 1 d . . . H21 H 1.1198 -0.1488 0.1029 0.019 Uiso 1 1 calc R . . C22 C 0.86412(11) 0.00695(12) 0.05295(10) 0.0160(2) Uani 1 1 d . . . H22 H 0.7705 0.0117 0.0889 0.019 Uiso 1 1 calc R . . C23 C 1.39049(12) -0.16722(12) 0.28730(11) 0.0192(3) Uani 1 1 d . . . C24 C 1.47696(14) -0.21250(14) 0.19117(13) 0.0286(3) Uani 1 1 d . . . H24A H 1.5406 -0.2733 0.2175 0.043 Uiso 1 1 calc R . . H24B H 1.5265 -0.1362 0.1225 0.043 Uiso 1 1 calc R . . H24C H 1.4190 -0.2569 0.1721 0.043 Uiso 1 1 calc R . . C25 C 1.32341(13) -0.28785(13) 0.39659(13) 0.0290(3) Uani 1 1 d . . . H25A H 1.2684 -0.2601 0.4588 0.043 Uiso 1 1 calc R . . H25B H 1.3924 -0.3428 0.4195 0.043 Uiso 1 1 calc R . . H25C H 1.2663 -0.3381 0.3817 0.043 Uiso 1 1 calc R . . C26 C 1.48122(13) -0.09333(13) 0.31360(12) 0.0243(3) Uani 1 1 d . . . H26A H 1.4264 -0.0645 0.3751 0.036 Uiso 1 1 calc R . . H26B H 1.5279 -0.0167 0.2439 0.036 Uiso 1 1 calc R . . H26C H 1.5472 -0.1516 0.3385 0.036 Uiso 1 1 calc R . . C27 C 0.61272(12) 0.34272(12) 0.16484(11) 0.0197(3) Uani 1 1 d . . . C28 C 0.49803(14) 0.27368(15) 0.27932(13) 0.0317(3) Uani 1 1 d . . . H28A H 0.4163 0.3200 0.2788 0.048 Uiso 1 1 calc R . . H28B H 0.5218 0.2737 0.3429 0.048 Uiso 1 1 calc R . . H28C H 0.4824 0.1830 0.2898 0.048 Uiso 1 1 calc R . . C29 C 0.57837(14) 0.33204(15) 0.06777(13) 0.0289(3) Uani 1 1 d . . . H29A H 0.5753 0.2399 0.0780 0.043 Uiso 1 1 calc R . . H29B H 0.6471 0.3828 -0.0069 0.043 Uiso 1 1 calc R . . H29C H 0.4907 0.3666 0.0702 0.043 Uiso 1 1 calc R . . C30 C 0.62339(15) 0.48776(14) 0.14546(15) 0.0331(4) Uani 1 1 d . . . H30A H 0.5364 0.5247 0.1490 0.050 Uiso 1 1 calc R . . H30B H 0.6914 0.5359 0.0695 0.050 Uiso 1 1 calc R . . H30C H 0.6491 0.4953 0.2055 0.050 Uiso 1 1 calc R . . O1A O 1.00475(9) 0.19143(9) 0.41791(8) 0.0234(2) Uani 1 1 d . . . H1A H 1.0555 0.1543 0.4543 0.035 Uiso 1 1 calc R . . C1A C 1.07033(14) 0.31184(13) 0.32683(12) 0.0255(3) Uani 1 1 d . . . H1A1 H 1.1679 0.3017 0.2969 0.031 Uiso 1 1 calc R . . H1A2 H 1.0370 0.3319 0.2630 0.031 Uiso 1 1 calc R . . C2A C 1.04731(14) 0.42501(13) 0.36519(12) 0.0254(3) Uani 1 1 d . . . H2A1 H 0.9497 0.4352 0.3954 0.030 Uiso 1 1 calc R . . H2A2 H 1.0813 0.4056 0.4285 0.030 Uiso 1 1 calc R . . C3A C 1.11730(17) 0.55253(14) 0.26669(14) 0.0366(4) Uani 1 1 d . . . H3A1 H 1.0849 0.5713 0.2033 0.055 Uiso 1 1 calc R . . H3A2 H 1.0977 0.6243 0.2940 0.055 Uiso 1 1 calc R . . H3A3 H 1.2144 0.5443 0.2393 0.055 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 O1 0.0191(4) 0.0165(4) 0.0127(4) -0.0055(3) -0.0054(3) -0.0012(3) C1 0.0136(5) 0.0137(5) 0.0140(6) -0.0056(5) -0.0044(4) -0.0009(4) C2 0.0157(5) 0.0145(6) 0.0161(6) -0.0048(5) -0.0058(4) 0.0000(4) C3 0.0147(5) 0.0149(6) 0.0203(6) -0.0071(5) -0.0072(5) 0.0011(4) C4 0.0131(5) 0.0186(6) 0.0217(6) -0.0068(5) -0.0035(5) -0.0014(4) C5 0.0167(5) 0.0152(6) 0.0173(6) -0.0038(5) -0.0041(5) -0.0021(4) C6 0.0143(5) 0.0135(5) 0.0147(6) -0.0055(5) -0.0049(4) 0.0001(4) C7 0.0154(5) 0.0132(5) 0.0143(6) -0.0053(5) -0.0053(4) -0.0004(4) C8 0.0184(5) 0.0146(6) 0.0145(6) -0.0041(5) -0.0049(4) -0.0015(4) C9 0.0230(6) 0.0123(6) 0.0169(6) -0.0025(5) -0.0088(5) 0.0010(4) C10 0.0187(5) 0.0139(6) 0.0177(6) -0.0072(5) -0.0088(5) 0.0032(4) C11 0.0157(5) 0.0151(6) 0.0146(6) -0.0048(5) -0.0051(4) 0.0002(4) C12 0.0164(5) 0.0126(5) 0.0129(5) -0.0045(4) -0.0063(4) 0.0006(4) C13 0.0127(5) 0.0136(5) 0.0113(5) -0.0031(4) -0.0042(4) 0.0002(4) C14 0.0100(5) 0.0135(5) 0.0152(6) -0.0033(5) -0.0051(4) 0.0014(4) C15 0.0151(5) 0.0185(6) 0.0134(6) -0.0041(5) -0.0053(4) 0.0006(4) C16 0.0174(5) 0.0165(6) 0.0158(6) -0.0003(5) -0.0045(5) -0.0026(4) C17 0.0198(6) 0.0142(6) 0.0223(6) -0.0042(5) -0.0073(5) -0.0025(4) C18 0.0193(6) 0.0191(6) 0.0175(6) -0.0074(5) -0.0060(5) -0.0003(5) C19 0.0127(5) 0.0150(6) 0.0135(6) -0.0036(5) -0.0046(4) 0.0012(4) C20 0.0161(5) 0.0137(6) 0.0126(6) -0.0050(5) -0.0045(4) -0.0017(4) C21 0.0167(5) 0.0158(6) 0.0145(6) -0.0045(5) -0.0066(4) 0.0012(4) C22 0.0135(5) 0.0182(6) 0.0150(6) -0.0067(5) -0.0033(4) -0.0002(4) C23 0.0151(5) 0.0171(6) 0.0249(7) -0.0065(5) -0.0088(5) 0.0019(4) C24 0.0271(7) 0.0279(7) 0.0376(8) -0.0179(7) -0.0156(6) 0.0116(6) C25 0.0207(6) 0.0213(7) 0.0384(8) -0.0015(6) -0.0145(6) 0.0018(5) C26 0.0202(6) 0.0243(7) 0.0318(8) -0.0107(6) -0.0136(5) 0.0023(5) C27 0.0194(6) 0.0159(6) 0.0232(7) -0.0057(5) -0.0097(5) 0.0044(5) C28 0.0224(6) 0.0324(8) 0.0297(8) -0.0073(6) -0.0051(6) 0.0116(6) C29 0.0258(7) 0.0313(8) 0.0351(8) -0.0123(6) -0.0181(6) 0.0044(6) C30 0.0304(7) 0.0203(7) 0.0573(10) -0.0187(7) -0.0233(7) 0.0100(6) O1A 0.0306(5) 0.0172(5) 0.0228(5) -0.0030(4) -0.0147(4) -0.0015(4) C1A 0.0342(7) 0.0210(7) 0.0189(7) -0.0055(5) -0.0084(6) -0.0027(5) C2A 0.0315(7) 0.0213(7) 0.0258(7) -0.0078(6) -0.0147(6) 0.0026(5) C3A 0.0442(9) 0.0225(7) 0.0408(9) -0.0059(7) -0.0185(7) -0.0048(6) _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 O1 C13 1.4363(14) . ? O1 H1 0.8400 . ? C1 C2 1.3828(16) . ? C1 C6 1.3923(16) . ? C1 C13 1.5330(15) . ? C2 C3 1.3994(16) . ? C2 H2 0.9500 . ? C3 C4 1.4026(17) . ? C3 C23 1.5305(17) . ? C4 C5 1.3879(17) . ? C4 H4 0.9500 . ? C5 C6 1.3861(16) . ? C5 H5 0.9500 . ? C6 C7 1.4669(16) . ? C7 C8 1.3872(16) . ? C7 C12 1.3963(15) . ? C8 C9 1.3894(17) . ? C8 H8 0.9500 . ? C9 C10 1.4009(17) . ? C9 H9 0.9500 . ? C10 C11 1.3998(17) . ? C10 C27 1.5310(16) . ? C11 C12 1.3822(16) . ? C11 H11 0.9500 . ? C12 C13 1.5277(16) . ? C13 C14 1.5345(16) . ? C14 C15 1.3939(16) . ? C14 C19 1.4066(16) . ? C15 C16 1.3888(17) . ? C15 H15 0.9500 . ? C16 C17 1.3804(18) . ? C16 H16 0.9500 . ? C17 C18 1.3878(17) . ? C17 H17 0.9500 . ? C18 C19 1.3952(16) . ? C18 H18 0.9500 . ? C19 C20 1.4950(16) . ? C20 C22 1.3935(16) . ? C20 C21 1.3937(16) . ? C21 C22 1.3841(16) 2_755 ? C21 H21 0.9500 . ? C22 C21 1.3841(16) 2_755 ? C22 H22 0.9500 . ? C23 C25 1.5258(18) . ? C23 C26 1.5348(17) . ? C23 C24 1.5353(19) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.5276(18) . ? C27 C29 1.5322(19) . ? C27 C30 1.5346(18) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? O1A C1A 1.4257(15) . ? O1A H1A 0.8400 . ? C1A C2A 1.5085(19) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.5204(19) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 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 C13 O1 H1 109.5 . . ? C2 C1 C6 121.50(10) . . ? C2 C1 C13 127.84(10) . . ? C6 C1 C13 110.63(10) . . ? C1 C2 C3 119.70(11) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 117.99(11) . . ? C2 C3 C23 122.63(11) . . ? C4 C3 C23 119.37(10) . . ? C5 C4 C3 122.35(11) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C6 C5 C4 118.68(11) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 119.76(11) . . ? C5 C6 C7 131.58(11) . . ? C1 C6 C7 108.67(10) . . ? C8 C7 C12 119.53(11) . . ? C8 C7 C6 131.49(11) . . ? C12 C7 C6 108.98(10) . . ? C7 C8 C9 118.80(11) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 C10 122.26(11) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 118.12(11) . . ? C11 C10 C27 122.46(11) . . ? C9 C10 C27 119.39(11) . . ? C12 C11 C10 119.70(11) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.51(11) . . ? C11 C12 C13 128.03(10) . . ? C7 C12 C13 110.42(10) . . ? O1 C13 C12 110.57(9) . . ? O1 C13 C1 110.85(9) . . ? C12 C13 C1 101.30(9) . . ? O1 C13 C14 106.95(9) . . ? C12 C13 C14 114.56(9) . . ? C1 C13 C14 112.63(9) . . ? C15 C14 C19 118.62(11) . . ? C15 C14 C13 119.29(10) . . ? C19 C14 C13 122.07(10) . . ? C16 C15 C14 121.44(11) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 120.04(11) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.13(11) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 121.70(12) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C18 C19 C14 119.01(11) . . ? C18 C19 C20 116.96(11) . . ? C14 C19 C20 124.01(10) . . ? C22 C20 C21 118.66(11) . . ? C22 C20 C19 119.66(10) . . ? C21 C20 C19 121.63(11) . . ? C22 C21 C20 120.34(11) 2_755 . ? C22 C21 H21 119.8 2_755 . ? C20 C21 H21 119.8 . . ? C21 C22 C20 120.99(10) 2_755 . ? C21 C22 H22 119.5 2_755 . ? C20 C22 H22 119.5 . . ? C25 C23 C3 112.57(10) . . ? C25 C23 C26 107.73(11) . . ? C3 C23 C26 109.24(10) . . ? C25 C23 C24 108.76(11) . . ? C3 C23 C24 109.25(11) . . ? C26 C23 C24 109.23(10) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C10 112.35(10) . . ? C28 C27 C29 108.61(11) . . ? C10 C27 C29 108.67(10) . . ? C28 C27 C30 107.76(11) . . ? C10 C27 C30 110.18(10) . . ? C29 C27 C30 109.22(11) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1A O1A H1A 109.5 . . ? O1A C1A C2A 112.55(11) . . ? O1A C1A H1A1 109.1 . . ? C2A C1A H1A1 109.1 . . ? O1A C1A H1A2 109.1 . . ? C2A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.8 . . ? C1A C2A C3A 111.71(12) . . ? C1A C2A H2A1 109.3 . . ? C3A C2A H2A1 109.3 . . ? C1A C2A H2A2 109.3 . . ? C3A C2A H2A2 109.3 . . ? H2A1 C2A H2A2 107.9 . . ? C2A C3A H3A1 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C2A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 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 C6 C1 C2 C3 0.39(18) . . . . ? C13 C1 C2 C3 -177.53(11) . . . . ? C1 C2 C3 C4 -1.60(17) . . . . ? C1 C2 C3 C23 177.55(11) . . . . ? C2 C3 C4 C5 1.59(19) . . . . ? C23 C3 C4 C5 -177.59(11) . . . . ? C3 C4 C5 C6 -0.31(19) . . . . ? C4 C5 C6 C1 -0.95(18) . . . . ? C4 C5 C6 C7 179.58(12) . . . . ? C2 C1 C6 C5 0.92(18) . . . . ? C13 C1 C6 C5 179.17(10) . . . . ? C2 C1 C6 C7 -179.50(11) . . . . ? C13 C1 C6 C7 -1.25(13) . . . . ? C5 C6 C7 C8 0.9(2) . . . . ? C1 C6 C7 C8 -178.58(12) . . . . ? C5 C6 C7 C12 -179.17(12) . . . . ? C1 C6 C7 C12 1.32(13) . . . . ? C12 C7 C8 C9 1.72(17) . . . . ? C6 C7 C8 C9 -178.39(12) . . . . ? C7 C8 C9 C10 0.82(18) . . . . ? C8 C9 C10 C11 -2.05(18) . . . . ? C8 C9 C10 C27 179.96(11) . . . . ? C9 C10 C11 C12 0.72(17) . . . . ? C27 C10 C11 C12 178.65(11) . . . . ? C10 C11 C12 C7 1.80(18) . . . . ? C10 C11 C12 C13 179.28(11) . . . . ? C8 C7 C12 C11 -3.06(18) . . . . ? C6 C7 C12 C11 177.03(11) . . . . ? C8 C7 C12 C13 179.06(10) . . . . ? C6 C7 C12 C13 -0.85(13) . . . . ? C11 C12 C13 O1 -60.04(15) . . . . ? C7 C12 C13 O1 117.67(10) . . . . ? C11 C12 C13 C1 -177.60(11) . . . . ? C7 C12 C13 C1 0.11(12) . . . . ? C11 C12 C13 C14 60.89(16) . . . . ? C7 C12 C13 C14 -121.40(11) . . . . ? C2 C1 C13 O1 61.46(15) . . . . ? C6 C1 C13 O1 -116.64(11) . . . . ? C2 C1 C13 C12 178.82(11) . . . . ? C6 C1 C13 C12 0.71(12) . . . . ? C2 C1 C13 C14 -58.33(16) . . . . ? C6 C1 C13 C14 123.57(11) . . . . ? O1 C13 C14 C15 -2.40(14) . . . . ? C12 C13 C14 C15 -125.30(11) . . . . ? C1 C13 C14 C15 119.62(11) . . . . ? O1 C13 C14 C19 179.00(9) . . . . ? C12 C13 C14 C19 56.10(14) . . . . ? C1 C13 C14 C19 -58.98(14) . . . . ? C19 C14 C15 C16 2.33(17) . . . . ? C13 C14 C15 C16 -176.31(10) . . . . ? C14 C15 C16 C17 -0.37(18) . . . . ? C15 C16 C17 C18 -1.43(18) . . . . ? C16 C17 C18 C19 1.25(19) . . . . ? C17 C18 C19 C14 0.73(18) . . . . ? C17 C18 C19 C20 -177.63(11) . . . . ? C15 C14 C19 C18 -2.48(16) . . . . ? C13 C14 C19 C18 176.13(10) . . . . ? C15 C14 C19 C20 175.76(11) . . . . ? C13 C14 C19 C20 -5.63(17) . . . . ? C18 C19 C20 C22 86.60(14) . . . . ? C14 C19 C20 C22 -91.67(14) . . . . ? C18 C19 C20 C21 -90.67(14) . . . . ? C14 C19 C20 C21 91.06(14) . . . . ? C22 C20 C21 C22 0.72(19) . . . 2_755 ? C19 C20 C21 C22 178.02(11) . . . 2_755 ? C21 C20 C22 C21 -0.73(19) . . . 2_755 ? C19 C20 C22 C21 -178.08(11) . . . 2_755 ? C2 C3 C23 C25 0.98(17) . . . . ? C4 C3 C23 C25 -179.88(12) . . . . ? C2 C3 C23 C26 -118.65(13) . . . . ? C4 C3 C23 C26 60.49(15) . . . . ? C2 C3 C23 C24 121.91(13) . . . . ? C4 C3 C23 C24 -58.95(15) . . . . ? C11 C10 C27 C28 12.64(17) . . . . ? C9 C10 C27 C28 -169.46(12) . . . . ? C11 C10 C27 C29 -107.56(13) . . . . ? C9 C10 C27 C29 70.34(14) . . . . ? C11 C10 C27 C30 132.81(13) . . . . ? C9 C10 C27 C30 -49.29(16) . . . . ? O1A C1A C2A C3A 179.64(11) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.361 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.046 data_klien19new _database_code_depnum_ccdc_archive 'CCDC 900659' #TrackingRef 'Klien19new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H30 O2, 2(C4 H11 N)' _chemical_formula_sum 'C52 H52 N2 O2' _chemical_formula_weight 736.96 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2198(6) _cell_length_b 16.0642(8) _cell_length_c 9.3447(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.109(2) _cell_angle_gamma 90.00 _cell_volume 2060.82(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2535 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 28.32 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18673 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4692 _reflns_number_gt 3569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The N-H bond length have been restraint to a target value of 0.90(0.01) Angstrom. ; _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^)+(0.0638P)^2^+0.4176P] 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 4692 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 O1 O 0.36926(7) 0.54142(6) 0.35257(10) 0.0179(2) Uani 1 1 d . . . H1 H 0.3948 0.4941 0.3700 0.027 Uiso 1 1 calc R . . C1 C 0.21193(9) 0.48658(8) 0.36725(14) 0.0148(3) Uani 1 1 d . . . C2 C 0.19210(10) 0.51361(9) 0.49657(15) 0.0185(3) Uani 1 1 d . . . H2 H 0.2163 0.5655 0.5396 0.022 Uiso 1 1 calc R . . C3 C 0.13580(11) 0.46298(9) 0.56231(16) 0.0226(3) Uani 1 1 d . . . H3 H 0.1216 0.4802 0.6517 0.027 Uiso 1 1 calc R . . C4 C 0.10028(10) 0.38770(9) 0.49855(15) 0.0226(3) Uani 1 1 d . . . H4 H 0.0615 0.3541 0.5445 0.027 Uiso 1 1 calc R . . C5 C 0.12040(10) 0.36026(9) 0.36827(15) 0.0190(3) Uani 1 1 d . . . H5 H 0.0955 0.3087 0.3247 0.023 Uiso 1 1 calc R . . C6 C 0.17787(9) 0.41030(8) 0.30355(14) 0.0149(3) Uani 1 1 d . . . C7 C 0.20896(9) 0.40064(8) 0.16561(14) 0.0149(3) Uani 1 1 d . . . C8 C 0.19607(10) 0.33619(9) 0.06364(15) 0.0189(3) Uani 1 1 d . . . H8 H 0.1622 0.2870 0.0769 0.023 Uiso 1 1 calc R . . C9 C 0.23388(10) 0.34521(9) -0.05856(15) 0.0223(3) Uani 1 1 d . . . H9 H 0.2254 0.3017 -0.1295 0.027 Uiso 1 1 calc R . . C10 C 0.28377(10) 0.41673(9) -0.07875(15) 0.0226(3) Uani 1 1 d . . . H10 H 0.3090 0.4217 -0.1631 0.027 Uiso 1 1 calc R . . C11 C 0.29701(10) 0.48119(9) 0.02402(15) 0.0188(3) Uani 1 1 d . . . H11 H 0.3313 0.5301 0.0110 0.023 Uiso 1 1 calc R . . C12 C 0.25933(9) 0.47269(8) 0.14525(14) 0.0148(3) Uani 1 1 d . . . C13 C 0.26915(9) 0.53262(8) 0.27425(14) 0.0149(3) Uani 1 1 d . . . C14 C 0.22695(10) 0.61947(8) 0.23246(14) 0.0165(3) Uani 1 1 d . . . C15 C 0.28069(11) 0.68919(9) 0.29402(17) 0.0240(3) Uani 1 1 d . . . H15 H 0.3447 0.6820 0.3559 0.029 Uiso 1 1 calc R . . C16 C 0.24287(12) 0.76884(9) 0.26695(19) 0.0292(4) Uani 1 1 d . . . H16 H 0.2806 0.8154 0.3112 0.035 Uiso 1 1 calc R . . C17 C 0.15057(11) 0.78065(9) 0.17590(18) 0.0277(3) Uani 1 1 d . . . H17 H 0.1243 0.8351 0.1569 0.033 Uiso 1 1 calc R . . C18 C 0.09670(11) 0.71215(9) 0.11258(16) 0.0226(3) Uani 1 1 d . . . H18 H 0.0334 0.7204 0.0488 0.027 Uiso 1 1 calc R . . C19 C 0.13255(10) 0.63159(8) 0.13971(14) 0.0165(3) Uani 1 1 d . . . C20 C 0.06593(9) 0.56234(8) 0.06873(14) 0.0153(3) Uani 1 1 d . . . C21 C 0.05941(10) 0.53764(8) -0.07678(15) 0.0170(3) Uani 1 1 d . . . H21 H 0.0997 0.5635 -0.1304 0.020 Uiso 1 1 calc R . . C22 C 0.00478(10) 0.52390(8) 0.14364(14) 0.0167(3) Uani 1 1 d . . . H22 H 0.0074 0.5403 0.2422 0.020 Uiso 1 1 calc R . . N1A N 0.53380(8) 0.61053(7) 0.59937(12) 0.0179(3) Uani 1 1 d D . . H1A H 0.4775(8) 0.5949(10) 0.5330(15) 0.027(4) Uiso 1 1 d D . . C1A C 0.59851(12) 0.64816(10) 0.38793(16) 0.0268(3) Uani 1 1 d . . . H1A1 H 0.6406 0.5989 0.4054 0.040 Uiso 1 1 calc R . . H1A2 H 0.6306 0.6930 0.3473 0.040 Uiso 1 1 calc R . . H1A3 H 0.5364 0.6344 0.3173 0.040 Uiso 1 1 calc R . . C2A C 0.57995(11) 0.67633(9) 0.53287(16) 0.0208(3) Uani 1 1 d . . . H2A1 H 0.6425 0.6922 0.6028 0.025 Uiso 1 1 calc R . . H2A2 H 0.5373 0.7260 0.5149 0.025 Uiso 1 1 calc R . . C3A C 0.51109(11) 0.63914(9) 0.73605(16) 0.0210(3) Uani 1 1 d . . . H3A1 H 0.4709 0.6902 0.7149 0.025 Uiso 1 1 calc R . . H3A2 H 0.5724 0.6531 0.8108 0.025 Uiso 1 1 calc R . . C4A C 0.45680(11) 0.57314(10) 0.79823(18) 0.0290(4) Uani 1 1 d . . . H4A1 H 0.3937 0.5624 0.7277 0.043 Uiso 1 1 calc R . . H4A2 H 0.4464 0.5925 0.8923 0.043 Uiso 1 1 calc R . . H4A3 H 0.4952 0.5217 0.8150 0.043 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 O1 0.0109(5) 0.0172(5) 0.0230(5) -0.0013(4) -0.0002(4) -0.0003(4) C1 0.0109(6) 0.0172(7) 0.0150(6) 0.0017(5) 0.0008(5) 0.0022(5) C2 0.0156(7) 0.0210(7) 0.0179(6) -0.0030(5) 0.0025(5) 0.0017(6) C3 0.0200(8) 0.0319(8) 0.0170(7) 0.0003(6) 0.0067(6) 0.0041(6) C4 0.0196(7) 0.0270(8) 0.0226(7) 0.0064(6) 0.0080(6) -0.0002(6) C5 0.0161(7) 0.0172(7) 0.0224(7) 0.0025(5) 0.0030(6) -0.0006(5) C6 0.0113(6) 0.0171(7) 0.0145(6) 0.0014(5) 0.0004(5) 0.0028(5) C7 0.0108(6) 0.0171(7) 0.0151(6) 0.0003(5) 0.0001(5) 0.0033(5) C8 0.0151(7) 0.0184(7) 0.0211(7) -0.0019(5) 0.0008(5) 0.0014(5) C9 0.0201(8) 0.0265(8) 0.0182(7) -0.0073(6) 0.0011(6) 0.0037(6) C10 0.0182(7) 0.0341(9) 0.0156(7) -0.0009(6) 0.0046(5) 0.0046(6) C11 0.0142(7) 0.0232(7) 0.0188(7) 0.0025(5) 0.0038(5) 0.0014(6) C12 0.0107(6) 0.0166(7) 0.0151(6) 0.0009(5) 0.0000(5) 0.0026(5) C13 0.0105(6) 0.0181(7) 0.0151(6) -0.0015(5) 0.0012(5) -0.0015(5) C14 0.0151(7) 0.0168(7) 0.0182(6) 0.0003(5) 0.0053(5) -0.0006(5) C15 0.0167(7) 0.0213(8) 0.0312(8) -0.0016(6) 0.0011(6) -0.0023(6) C16 0.0242(8) 0.0171(8) 0.0433(9) -0.0042(6) 0.0033(7) -0.0057(6) C17 0.0249(8) 0.0159(7) 0.0412(9) 0.0023(6) 0.0065(7) 0.0006(6) C18 0.0171(7) 0.0208(7) 0.0285(7) 0.0037(6) 0.0031(6) 0.0012(6) C19 0.0149(7) 0.0180(7) 0.0176(6) 0.0000(5) 0.0060(5) -0.0012(5) C20 0.0103(6) 0.0159(7) 0.0178(6) 0.0022(5) 0.0000(5) 0.0028(5) C21 0.0122(7) 0.0206(7) 0.0178(6) 0.0049(5) 0.0034(5) 0.0010(5) C22 0.0139(7) 0.0202(7) 0.0152(6) 0.0008(5) 0.0024(5) 0.0029(5) N1A 0.0144(6) 0.0192(6) 0.0183(6) -0.0020(5) 0.0010(5) -0.0008(5) C1A 0.0287(8) 0.0276(8) 0.0246(7) 0.0035(6) 0.0075(6) 0.0046(7) C2A 0.0210(8) 0.0183(7) 0.0229(7) 0.0007(5) 0.0054(6) 0.0005(6) C3A 0.0188(7) 0.0220(7) 0.0223(7) -0.0021(5) 0.0058(6) 0.0012(6) C4A 0.0220(8) 0.0339(9) 0.0330(8) 0.0019(7) 0.0107(7) -0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4280(16) . ? O1 H1 0.8400 . ? C1 C2 1.3807(18) . ? C1 C6 1.3929(18) . ? C1 C13 1.5273(18) . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.3928(19) . ? C4 H4 0.9500 . ? C5 C6 1.3920(18) . ? C5 H5 0.9500 . ? C6 C7 1.4758(18) . ? C7 C8 1.3866(18) . ? C7 C12 1.3999(18) . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C9 C10 1.389(2) . ? C9 H9 0.9500 . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C11 C12 1.3804(18) . ? C11 H11 0.9500 . ? C12 C13 1.5204(18) . ? C13 C14 1.5286(19) . ? C14 C15 1.393(2) . ? C14 C19 1.4087(19) . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.379(2) . ? C16 H16 0.9500 . ? C17 C18 1.382(2) . ? C17 H17 0.9500 . ? C18 C19 1.3899(19) . ? C18 H18 0.9500 . ? C19 C20 1.4991(18) . ? C20 C22 1.3945(18) . ? C20 C21 1.3962(18) . ? C21 C22 1.3796(19) 3_565 ? C21 H21 0.9500 . ? C22 C21 1.3796(19) 3_565 ? C22 H22 0.9500 . ? N1A C2A 1.4652(18) . ? N1A C3A 1.4703(17) . ? N1A H1A 0.911(9) . ? C1A C2A 1.515(2) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.514(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 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 C13 O1 H1 109.5 . . ? C2 C1 C6 121.53(12) . . ? C2 C1 C13 127.33(12) . . ? C6 C1 C13 111.12(11) . . ? C1 C2 C3 118.36(13) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.53(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.18(13) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 118.33(13) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 120.04(12) . . ? C5 C6 C7 131.47(12) . . ? C1 C6 C7 108.40(11) . . ? C8 C7 C12 120.30(12) . . ? C8 C7 C6 131.51(12) . . ? C12 C7 C6 108.19(11) . . ? C7 C8 C9 118.45(13) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 121.22(13) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.26(13) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 118.76(13) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C7 121.01(12) . . ? C11 C12 C13 127.80(12) . . ? C7 C12 C13 111.11(11) . . ? O1 C13 C12 110.02(10) . . ? O1 C13 C1 111.35(10) . . ? C12 C13 C1 101.08(10) . . ? O1 C13 C14 108.24(10) . . ? C12 C13 C14 115.25(11) . . ? C1 C13 C14 110.82(10) . . ? C15 C14 C19 118.37(13) . . ? C15 C14 C13 119.46(12) . . ? C19 C14 C13 122.07(12) . . ? C16 C15 C14 121.48(14) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 120.11(14) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.13(14) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 121.81(14) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C18 C19 C14 119.10(12) . . ? C18 C19 C20 116.79(12) . . ? C14 C19 C20 124.10(12) . . ? C22 C20 C21 118.12(12) . . ? C22 C20 C19 120.76(12) . . ? C21 C20 C19 121.04(12) . . ? C22 C21 C20 120.85(12) 3_565 . ? C22 C21 H21 119.6 3_565 . ? C20 C21 H21 119.6 . . ? C21 C22 C20 121.03(12) 3_565 . ? C21 C22 H22 119.5 3_565 . ? C20 C22 H22 119.5 . . ? C2A N1A C3A 111.53(11) . . ? C2A N1A H1A 108.8(10) . . ? C3A N1A H1A 109.0(10) . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? N1A C2A C1A 111.43(12) . . ? N1A C2A H2A1 109.3 . . ? C1A C2A H2A1 109.3 . . ? N1A C2A H2A2 109.3 . . ? C1A C2A H2A2 109.3 . . ? H2A1 C2A H2A2 108.0 . . ? N1A C3A C4A 111.34(12) . . ? N1A C3A H3A1 109.4 . . ? C4A C3A H3A1 109.4 . . ? N1A C3A H3A2 109.4 . . ? C4A C3A H3A2 109.4 . . ? H3A1 C3A H3A2 108.0 . . ? C3A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C3A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 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 C6 C1 C2 C3 -0.7(2) . . . . ? C13 C1 C2 C3 178.06(13) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C4 C5 C6 C1 -1.41(19) . . . . ? C4 C5 C6 C7 -177.57(13) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? C13 C1 C6 C5 -177.32(11) . . . . ? C2 C1 C6 C7 178.57(12) . . . . ? C13 C1 C6 C7 -0.35(14) . . . . ? C5 C6 C7 C8 -5.1(2) . . . . ? C1 C6 C7 C8 178.40(14) . . . . ? C5 C6 C7 C12 174.81(13) . . . . ? C1 C6 C7 C12 -1.69(14) . . . . ? C12 C7 C8 C9 -0.27(19) . . . . ? C6 C7 C8 C9 179.63(13) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C8 C9 C10 C11 0.1(2) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 C7 0.2(2) . . . . ? C10 C11 C12 C13 176.74(13) . . . . ? C8 C7 C12 C11 0.04(19) . . . . ? C6 C7 C12 C11 -179.88(12) . . . . ? C8 C7 C12 C13 -177.00(12) . . . . ? C6 C7 C12 C13 3.08(14) . . . . ? C11 C12 C13 O1 -62.11(17) . . . . ? C7 C12 C13 O1 114.68(12) . . . . ? C11 C12 C13 C1 -179.89(13) . . . . ? C7 C12 C13 C1 -3.10(14) . . . . ? C11 C12 C13 C14 60.59(18) . . . . ? C7 C12 C13 C14 -122.63(12) . . . . ? C2 C1 C13 O1 66.38(17) . . . . ? C6 C1 C13 O1 -114.78(12) . . . . ? C2 C1 C13 C12 -176.81(13) . . . . ? C6 C1 C13 C12 2.03(14) . . . . ? C2 C1 C13 C14 -54.17(17) . . . . ? C6 C1 C13 C14 124.67(12) . . . . ? O1 C13 C14 C15 -11.06(16) . . . . ? C12 C13 C14 C15 -134.70(13) . . . . ? C1 C13 C14 C15 111.31(14) . . . . ? O1 C13 C14 C19 172.66(11) . . . . ? C12 C13 C14 C19 49.03(16) . . . . ? C1 C13 C14 C19 -64.96(15) . . . . ? C19 C14 C15 C16 0.6(2) . . . . ? C13 C14 C15 C16 -175.77(13) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 0.1(2) . . . . ? C16 C17 C18 C19 0.9(2) . . . . ? C17 C18 C19 C14 -1.0(2) . . . . ? C17 C18 C19 C20 177.98(13) . . . . ? C15 C14 C19 C18 0.24(19) . . . . ? C13 C14 C19 C18 176.55(12) . . . . ? C15 C14 C19 C20 -178.65(12) . . . . ? C13 C14 C19 C20 -2.34(19) . . . . ? C18 C19 C20 C22 -91.97(15) . . . . ? C14 C19 C20 C22 86.95(16) . . . . ? C18 C19 C20 C21 84.48(16) . . . . ? C14 C19 C20 C21 -96.60(16) . . . . ? C22 C20 C21 C22 -0.9(2) . . . 3_565 ? C19 C20 C21 C22 -177.45(12) . . . 3_565 ? C21 C20 C22 C21 0.9(2) . . . 3_565 ? C19 C20 C22 C21 177.46(12) . . . 3_565 ? C3A N1A C2A C1A -177.05(12) . . . . ? C2A N1A C3A C4A 175.82(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.321 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.043 data_klien5cc _database_code_depnum_ccdc_archive 'CCDC 900660' #TrackingRef 'Klien5fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H30 O2, 2(C3 H8 O)' _chemical_formula_sum 'C50 H46 O4' _chemical_formula_weight 710.87 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 0.0000 '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' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 27.8442(11) _cell_length_b 9.5895(3) _cell_length_c 14.2430(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.527(2) _cell_angle_gamma 90.00 _cell_volume 3802.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3690 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.11 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.077 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 23193 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.70 _reflns_number_total 3985 _reflns_number_gt 3404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+7.5784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 3985 _refine_ls_number_parameters 493 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.076 _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 O1 O 0.76723(11) 0.6358(3) 0.9288(2) 0.0182(7) Uani 1 1 d . . . H1 H 0.7694 0.7164 0.9515 0.027 Uiso 1 1 calc R . . O2 O 0.38129(11) 0.3580(3) 0.9259(2) 0.0176(7) Uani 1 1 d . . . H2 H 0.3779 0.2736 0.9115 0.026 Uiso 1 1 calc R . . C1 C 0.68593(17) 0.6783(5) 0.9837(3) 0.0175(10) Uani 1 1 d . . . C2 C 0.68706(18) 0.6645(5) 1.0798(4) 0.0233(10) Uani 1 1 d . . . H2A H 0.7084 0.6003 1.1092 0.028 Uiso 1 1 calc R . . C3 C 0.6565(2) 0.7460(6) 1.1327(4) 0.0308(13) Uani 1 1 d . . . H3 H 0.6569 0.7390 1.1992 0.037 Uiso 1 1 calc R . . C4 C 0.6247(2) 0.8396(6) 1.0875(4) 0.0348(14) Uani 1 1 d . . . H4 H 0.6032 0.8934 1.1241 0.042 Uiso 1 1 calc R . . C5 C 0.62444(18) 0.8542(5) 0.9907(4) 0.0284(12) Uani 1 1 d . . . H5 H 0.6033 0.9182 0.9606 0.034 Uiso 1 1 calc R . . C6 C 0.65588(16) 0.7729(5) 0.9389(3) 0.0191(10) Uani 1 1 d . . . C7 C 0.66478(17) 0.7676(5) 0.8377(3) 0.0191(9) Uani 1 1 d . . . C8 C 0.6446(2) 0.8418(6) 0.7627(4) 0.0315(12) Uani 1 1 d . . . H8 H 0.6201 0.9087 0.7734 0.038 Uiso 1 1 calc R . . C9 C 0.6607(2) 0.8166(6) 0.6726(4) 0.0316(13) Uani 1 1 d . . . H9 H 0.6473 0.8673 0.6214 0.038 Uiso 1 1 calc R . . C10 C 0.6964(2) 0.7177(6) 0.6561(4) 0.0282(11) Uani 1 1 d . . . H10 H 0.7073 0.7018 0.5940 0.034 Uiso 1 1 calc R . . C11 C 0.71615(17) 0.6417(5) 0.7313(3) 0.0200(10) Uani 1 1 d . . . H11 H 0.7402 0.5734 0.7207 0.024 Uiso 1 1 calc R . . C12 C 0.70015(15) 0.6679(5) 0.8207(3) 0.0156(9) Uani 1 1 d . . . C13 C 0.71726(15) 0.6023(5) 0.9120(3) 0.0132(9) Uani 1 1 d . . . C14 C 0.71299(16) 0.4429(5) 0.9124(3) 0.0133(9) Uani 1 1 d . . . C15 C 0.75460(16) 0.3628(5) 0.9150(3) 0.0172(9) Uani 1 1 d . . . H15 H 0.7848 0.4085 0.9182 0.021 Uiso 1 1 calc R . . C16 C 0.75335(18) 0.2177(5) 0.9130(3) 0.0206(10) Uani 1 1 d . . . H16 H 0.7823 0.1655 0.9151 0.025 Uiso 1 1 calc R . . C17 C 0.70948(17) 0.1501(5) 0.9080(3) 0.0189(9) Uani 1 1 d . . . H17 H 0.7081 0.0511 0.9056 0.023 Uiso 1 1 calc R . . C18 C 0.66805(17) 0.2269(5) 0.9066(3) 0.0161(9) Uani 1 1 d . . . H18 H 0.6381 0.1795 0.9041 0.019 Uiso 1 1 calc R . . C19 C 0.66830(16) 0.3740(5) 0.9087(3) 0.0138(9) Uani 1 1 d . . . C20 C 0.62081(15) 0.4442(4) 0.9106(3) 0.0138(9) Uani 1 1 d . . . C21 C 0.59676(16) 0.4596(5) 0.9958(3) 0.0166(9) Uani 1 1 d . . . H21 H 0.6122 0.4316 1.0525 0.020 Uiso 1 1 calc R . . C22 C 0.55121(16) 0.5143(5) 0.9991(3) 0.0167(9) Uani 1 1 d . . . H22 H 0.5357 0.5244 1.0578 0.020 Uiso 1 1 calc R . . C23 C 0.52762(16) 0.5550(5) 0.9172(3) 0.0158(9) Uani 1 1 d . . . C24 C 0.55093(17) 0.5426(5) 0.8321(3) 0.0180(10) Uani 1 1 d . . . H24 H 0.5356 0.5732 0.7760 0.022 Uiso 1 1 calc R . . C25 C 0.59698(16) 0.4852(5) 0.8287(3) 0.0166(9) Uani 1 1 d . . . H25 H 0.6123 0.4740 0.7698 0.020 Uiso 1 1 calc R . . C26 C 0.47949(15) 0.6258(5) 0.9218(3) 0.0148(9) Uani 1 1 d . . . C27 C 0.47971(17) 0.7703(5) 0.9228(3) 0.0186(10) Uani 1 1 d . . . H27 H 0.5095 0.8180 0.9181 0.022 Uiso 1 1 calc R . . C28 C 0.43802(18) 0.8474(5) 0.9306(3) 0.0198(10) Uani 1 1 d . . . H28 H 0.4392 0.9464 0.9314 0.024 Uiso 1 1 calc R . . C29 C 0.39443(16) 0.7783(5) 0.9371(3) 0.0203(10) Uani 1 1 d . . . H29 H 0.3654 0.8297 0.9428 0.024 Uiso 1 1 calc R . . C30 C 0.39342(16) 0.6347(5) 0.9351(3) 0.0193(10) Uani 1 1 d . . . H30 H 0.3633 0.5886 0.9387 0.023 Uiso 1 1 calc R . . C31 C 0.43519(16) 0.5539(5) 0.9280(3) 0.0150(9) Uani 1 1 d . . . C32 C 0.43114(16) 0.3943(5) 0.9221(3) 0.0167(10) Uani 1 1 d . . . C33 C 0.45289(16) 0.3381(5) 0.8332(3) 0.0159(9) Uani 1 1 d . . . C34 C 0.44060(18) 0.3715(5) 0.7425(3) 0.0190(9) Uani 1 1 d . . . H34 H 0.4164 0.4389 0.7299 0.023 Uiso 1 1 calc R . . C35 C 0.46414(19) 0.3050(6) 0.6691(4) 0.0268(11) Uani 1 1 d . . . H35 H 0.4563 0.3267 0.6058 0.032 Uiso 1 1 calc R . . C36 C 0.5003(2) 0.2037(6) 0.6905(4) 0.0334(13) Uani 1 1 d . . . H36 H 0.5161 0.1571 0.6408 0.040 Uiso 1 1 calc R . . C37 C 0.51222(18) 0.1733(5) 0.7804(4) 0.0269(11) Uani 1 1 d . . . H37 H 0.5368 0.1070 0.7934 0.032 Uiso 1 1 calc R . . C38 C 0.48841(17) 0.2395(5) 0.8545(3) 0.0193(10) Uani 1 1 d . . . C39 C 0.49276(16) 0.2265(5) 0.9562(4) 0.0204(10) Uani 1 1 d . . . C40 C 0.5219(2) 0.1442(5) 1.0136(4) 0.0322(13) Uani 1 1 d . . . H40 H 0.5449 0.0831 0.9868 0.039 Uiso 1 1 calc R . . C41 C 0.5172(2) 0.1521(6) 1.1091(4) 0.0403(16) Uani 1 1 d . . . H41 H 0.5377 0.0972 1.1480 0.048 Uiso 1 1 calc R . . C42 C 0.4833(2) 0.2384(6) 1.1504(4) 0.0360(14) Uani 1 1 d . . . H42 H 0.4800 0.2406 1.2167 0.043 Uiso 1 1 calc R . . C43 C 0.4540(2) 0.3221(5) 1.0932(4) 0.0255(11) Uani 1 1 d . . . H43 H 0.4308 0.3823 1.1202 0.031 Uiso 1 1 calc R . . C44 C 0.45931(17) 0.3159(5) 0.9978(3) 0.0179(10) Uani 1 1 d . . . O1A O 0.85737(13) 0.6019(4) 0.8519(3) 0.0284(8) Uani 1 1 d . . . H1A H 0.8282 0.6006 0.8661 0.043 Uiso 1 1 calc R . . C1A C 0.8621(2) 0.5837(6) 0.7532(4) 0.0316(12) Uani 1 1 d . . . H1A1 H 0.8957 0.6040 0.7359 0.038 Uiso 1 1 calc R . . H1A2 H 0.8413 0.6528 0.7209 0.038 Uiso 1 1 calc R . . C2A C 0.84934(19) 0.4418(6) 0.7180(4) 0.0275(12) Uani 1 1 d . . . H2A1 H 0.8158 0.4201 0.7350 0.033 Uiso 1 1 calc R . . H2A2 H 0.8705 0.3719 0.7484 0.033 Uiso 1 1 calc R . . C3A C 0.8547(2) 0.4328(7) 0.6116(4) 0.0378(14) Uani 1 1 d . . . H3A1 H 0.8307 0.4927 0.5811 0.057 Uiso 1 1 calc R . . H3A2 H 0.8500 0.3361 0.5912 0.057 Uiso 1 1 calc R . . H3A3 H 0.8870 0.4638 0.5941 0.057 Uiso 1 1 calc R . . O1B O 0.78782(13) 0.8979(4) 0.9889(3) 0.0278(8) Uani 1 1 d . . . H1B H 0.8168 0.8757 0.9825 0.042 Uiso 1 1 calc R . . C1B C 0.77798(19) 0.9190(5) 1.0866(4) 0.0262(11) Uani 1 1 d . . . H1B1 H 0.7838 0.8304 1.1205 0.031 Uiso 1 1 calc R . . H1B2 H 0.7436 0.9425 1.0934 0.031 Uiso 1 1 calc R . . C2B C 0.8075(2) 1.0320(6) 1.1325(4) 0.0316(12) Uani 1 1 d . . . H2B1 H 0.7997 1.1229 1.1032 0.038 Uiso 1 1 calc R . . H2B2 H 0.8420 1.0131 1.1227 0.038 Uiso 1 1 calc R . . C3B C 0.7974(2) 1.0390(7) 1.2374(4) 0.0386(15) Uani 1 1 d . . . H3B1 H 0.7639 1.0656 1.2470 0.058 Uiso 1 1 calc R . . H3B2 H 0.8186 1.1084 1.2667 0.058 Uiso 1 1 calc R . . H3B3 H 0.8034 0.9475 1.2658 0.058 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 O1 0.0115(15) 0.0166(17) 0.0265(17) -0.0018(13) -0.0019(12) -0.0035(13) O2 0.0076(14) 0.0160(17) 0.0293(18) -0.0035(13) 0.0041(12) -0.0032(12) C1 0.016(2) 0.013(2) 0.024(2) -0.0029(18) 0.0019(18) -0.0029(18) C2 0.024(3) 0.017(2) 0.029(3) -0.002(2) 0.004(2) -0.009(2) C3 0.038(3) 0.025(3) 0.029(3) -0.009(2) 0.018(2) -0.012(2) C4 0.027(3) 0.027(3) 0.051(4) -0.016(3) 0.023(2) -0.006(2) C5 0.022(3) 0.013(2) 0.050(3) -0.008(2) 0.011(2) -0.0033(19) C6 0.013(2) 0.014(2) 0.031(3) -0.0022(19) 0.0032(18) -0.0038(18) C7 0.016(2) 0.011(2) 0.031(3) -0.0034(18) 0.0008(18) -0.0014(18) C8 0.027(3) 0.025(3) 0.043(3) 0.001(2) -0.009(2) 0.008(2) C9 0.045(3) 0.021(3) 0.028(3) 0.005(2) -0.014(2) 0.007(2) C10 0.038(3) 0.028(3) 0.019(2) 0.001(2) -0.003(2) -0.002(2) C11 0.022(2) 0.019(2) 0.018(2) -0.0001(18) -0.0025(18) -0.0017(19) C12 0.009(2) 0.013(2) 0.024(2) 0.0007(17) -0.0012(17) -0.0019(16) C13 0.007(2) 0.013(2) 0.020(2) -0.0021(17) 0.0019(16) 0.0023(16) C14 0.014(2) 0.011(2) 0.016(2) -0.0004(17) 0.0021(16) 0.0049(17) C15 0.009(2) 0.014(2) 0.028(2) -0.0005(18) 0.0022(17) 0.0023(17) C16 0.021(2) 0.017(3) 0.024(2) 0.0019(18) 0.0034(19) 0.0037(19) C17 0.020(2) 0.012(2) 0.025(2) -0.0038(19) 0.0029(18) 0.0010(19) C18 0.016(2) 0.011(2) 0.021(2) -0.0015(17) 0.0006(17) -0.0003(18) C19 0.013(2) 0.013(2) 0.016(2) -0.0011(17) 0.0020(16) 0.0043(17) C20 0.012(2) 0.005(2) 0.025(2) -0.0005(17) 0.0003(17) -0.0032(16) C21 0.013(2) 0.013(2) 0.023(2) 0.0020(17) -0.0023(17) 0.0022(17) C22 0.014(2) 0.017(2) 0.020(2) -0.0019(18) -0.0006(17) -0.0009(18) C23 0.012(2) 0.012(2) 0.024(2) -0.0033(17) 0.0007(17) -0.0026(17) C24 0.015(2) 0.020(2) 0.019(2) 0.0027(19) -0.0011(17) -0.0010(19) C25 0.014(2) 0.017(2) 0.019(2) -0.0008(18) 0.0040(17) -0.0009(18) C26 0.011(2) 0.018(2) 0.015(2) -0.0002(17) -0.0004(16) -0.0001(17) C27 0.017(2) 0.020(3) 0.018(2) -0.0009(18) 0.0026(17) -0.0036(19) C28 0.021(2) 0.012(2) 0.027(2) 0.0013(19) -0.0014(18) 0.000(2) C29 0.010(2) 0.019(3) 0.032(3) -0.001(2) -0.0019(18) 0.0039(18) C30 0.012(2) 0.023(3) 0.023(2) -0.0023(19) -0.0006(17) 0.0040(18) C31 0.016(2) 0.014(2) 0.015(2) -0.0016(17) -0.0014(16) 0.0006(18) C32 0.014(2) 0.016(2) 0.020(2) 0.0024(18) -0.0029(17) -0.0063(18) C33 0.013(2) 0.009(2) 0.025(2) -0.0006(17) 0.0010(17) -0.0071(17) C34 0.022(2) 0.012(2) 0.024(2) -0.0001(17) 0.0032(18) -0.0010(18) C35 0.029(3) 0.030(3) 0.022(2) -0.004(2) 0.007(2) 0.002(2) C36 0.037(3) 0.026(3) 0.038(3) -0.013(2) 0.022(2) 0.002(2) C37 0.020(2) 0.016(2) 0.045(3) -0.008(2) 0.007(2) 0.004(2) C38 0.018(2) 0.010(2) 0.030(2) -0.0016(18) -0.0004(19) 0.0004(18) C39 0.014(2) 0.008(2) 0.040(3) -0.0020(19) -0.0055(19) -0.0011(17) C40 0.032(3) 0.010(2) 0.054(4) 0.003(2) -0.018(2) 0.006(2) C41 0.051(4) 0.018(3) 0.051(4) 0.009(2) -0.031(3) -0.004(3) C42 0.061(4) 0.018(3) 0.029(3) 0.004(2) -0.019(3) -0.013(3) C43 0.038(3) 0.014(2) 0.024(2) -0.0021(19) -0.004(2) -0.005(2) C44 0.018(2) 0.008(2) 0.028(2) 0.0032(17) -0.0012(18) -0.0045(17) O1A 0.027(2) 0.0206(19) 0.038(2) -0.0078(16) 0.0110(16) -0.0034(16) C1A 0.038(3) 0.025(3) 0.032(3) 0.002(2) 0.011(2) -0.003(2) C2A 0.025(3) 0.030(3) 0.027(3) -0.003(2) 0.000(2) -0.002(2) C3A 0.040(3) 0.044(4) 0.029(3) -0.006(3) -0.005(2) -0.004(3) O1B 0.0196(18) 0.031(2) 0.033(2) -0.0049(16) 0.0065(15) -0.0045(16) C1B 0.023(3) 0.020(3) 0.035(3) -0.004(2) 0.009(2) -0.002(2) C2B 0.031(3) 0.035(3) 0.028(3) 0.002(2) 0.003(2) -0.005(2) C3B 0.042(4) 0.049(4) 0.025(3) 0.005(3) -0.001(2) -0.017(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 O1 C13 1.446(5) . ? O1 H1 0.8400 . ? O2 C32 1.433(5) . ? O2 H2 0.8400 . ? C1 C2 1.375(7) . ? C1 C6 1.386(7) . ? C1 C13 1.533(6) . ? C2 C3 1.384(7) . ? C2 H2A 0.9500 . ? C3 C4 1.411(9) . ? C3 H3 0.9500 . ? C4 C5 1.386(8) . ? C4 H4 0.9500 . ? C5 C6 1.390(7) . ? C5 H5 0.9500 . ? C6 C7 1.465(7) . ? C7 C8 1.397(7) . ? C7 C12 1.395(6) . ? C8 C9 1.384(8) . ? C8 H8 0.9500 . ? C9 C10 1.395(8) . ? C9 H9 0.9500 . ? C10 C11 1.404(7) . ? C10 H10 0.9500 . ? C11 C12 1.375(6) . ? C11 H11 0.9500 . ? C12 C13 1.517(6) . ? C13 C14 1.533(6) . ? C14 C15 1.390(6) . ? C14 C19 1.409(6) . ? C15 C16 1.393(7) . ? C15 H15 0.9500 . ? C16 C17 1.384(7) . ? C16 H16 0.9500 . ? C17 C18 1.369(7) . ? C17 H17 0.9500 . ? C18 C19 1.411(6) . ? C18 H18 0.9500 . ? C19 C20 1.484(6) . ? C20 C25 1.393(6) . ? C20 C21 1.399(6) . ? C21 C22 1.374(6) . ? C21 H21 0.9500 . ? C22 C23 1.389(7) . ? C22 H22 0.9500 . ? C23 C24 1.385(6) . ? C23 C26 1.504(6) . ? C24 C25 1.397(6) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.386(7) . ? C26 C31 1.416(6) . ? C27 C28 1.381(7) . ? C27 H27 0.9500 . ? C28 C29 1.387(7) . ? C28 H28 0.9500 . ? C29 C30 1.378(7) . ? C29 H29 0.9500 . ? C30 C31 1.402(6) . ? C30 H30 0.9500 . ? C31 C32 1.537(7) . ? C32 C33 1.507(6) . ? C32 C44 1.525(6) . ? C33 C34 1.371(7) . ? C33 C38 1.399(6) . ? C34 C35 1.393(7) . ? C34 H34 0.9500 . ? C35 C36 1.429(8) . ? C35 H35 0.9500 . ? C36 C37 1.352(8) . ? C36 H36 0.9500 . ? C37 C38 1.404(7) . ? C37 H37 0.9500 . ? C38 C39 1.458(7) . ? C39 C40 1.393(7) . ? C39 C44 1.401(7) . ? C40 C41 1.369(9) . ? C40 H40 0.9500 . ? C41 C42 1.392(10) . ? C41 H41 0.9500 . ? C42 C43 1.399(8) . ? C42 H42 0.9500 . ? C43 C44 1.370(7) . ? C43 H43 0.9500 . ? O1A C1A 1.424(7) . ? O1A H1A 0.8400 . ? C1A C2A 1.492(8) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.528(8) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? O1B C1B 1.435(6) . ? O1B H1B 0.8400 . ? C1B C2B 1.505(8) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B C3B 1.523(8) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B H3B1 0.9800 . ? C3B H3B2 0.9800 . ? C3B H3B3 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 C13 O1 H1 109.5 . . ? C32 O2 H2 109.5 . . ? C2 C1 C6 122.0(4) . . ? C2 C1 C13 127.5(4) . . ? C6 C1 C13 110.4(4) . . ? C1 C2 C3 118.6(5) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C2 C3 C4 119.8(5) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 121.0(5) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.3(5) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 120.2(5) . . ? C1 C6 C7 108.9(4) . . ? C5 C6 C7 130.9(5) . . ? C8 C7 C12 119.7(5) . . ? C8 C7 C6 131.6(5) . . ? C12 C7 C6 108.7(4) . . ? C9 C8 C7 119.2(5) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.8(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 119.9(5) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 118.9(5) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C7 121.4(4) . . ? C11 C12 C13 128.0(4) . . ? C7 C12 C13 110.6(4) . . ? O1 C13 C12 110.1(3) . . ? O1 C13 C1 109.7(4) . . ? C12 C13 C1 101.4(4) . . ? O1 C13 C14 107.2(3) . . ? C12 C13 C14 113.1(4) . . ? C1 C13 C14 115.2(4) . . ? C15 C14 C19 118.5(4) . . ? C15 C14 C13 119.1(4) . . ? C19 C14 C13 122.4(4) . . ? C14 C15 C16 122.1(4) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 119.4(4) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 122.3(4) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C14 C19 C18 118.3(4) . . ? C14 C19 C20 125.0(4) . . ? C18 C19 C20 116.7(4) . . ? C25 C20 C21 117.9(4) . . ? C25 C20 C19 122.0(4) . . ? C21 C20 C19 119.8(4) . . ? C22 C21 C20 121.3(4) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 120.6(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 119.2(4) . . ? C24 C23 C26 120.1(4) . . ? C22 C23 C26 120.3(4) . . ? C23 C24 C25 120.1(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C20 C25 C24 120.8(4) . . ? C20 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C27 C26 C31 119.3(4) . . ? C27 C26 C23 116.6(4) . . ? C31 C26 C23 124.1(4) . . ? C28 C27 C26 122.2(4) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C27 C28 C29 119.1(5) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? C30 C29 C28 119.6(4) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 122.5(4) . . ? C29 C30 H30 118.8 . . ? C31 C30 H30 118.8 . . ? C30 C31 C26 117.4(4) . . ? C30 C31 C32 119.6(4) . . ? C26 C31 C32 123.0(4) . . ? O2 C32 C33 110.0(4) . . ? O2 C32 C44 110.2(4) . . ? C33 C32 C44 102.1(4) . . ? O2 C32 C31 108.1(4) . . ? C33 C32 C31 111.8(4) . . ? C44 C32 C31 114.5(4) . . ? C34 C33 C38 122.1(4) . . ? C34 C33 C32 127.5(4) . . ? C38 C33 C32 110.4(4) . . ? C33 C34 C35 119.0(5) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C34 C35 C36 119.1(5) . . ? C34 C35 H35 120.5 . . ? C36 C35 H35 120.5 . . ? C37 C36 C35 121.0(5) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C36 C37 C38 120.1(5) . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C33 C38 C37 118.7(5) . . ? C33 C38 C39 109.0(4) . . ? C37 C38 C39 132.3(5) . . ? C40 C39 C44 119.0(5) . . ? C40 C39 C38 132.4(5) . . ? C44 C39 C38 108.5(4) . . ? C41 C40 C39 119.4(5) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C40 C41 C42 121.6(5) . . ? C40 C41 H41 119.2 . . ? C42 C41 H41 119.2 . . ? C41 C42 C43 119.3(5) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C44 C43 C42 119.0(5) . . ? C44 C43 H43 120.5 . . ? C42 C43 H43 120.5 . . ? C43 C44 C39 121.6(4) . . ? C43 C44 C32 128.4(5) . . ? C39 C44 C32 110.0(4) . . ? C1A O1A H1A 109.5 . . ? O1A C1A C2A 114.8(4) . . ? O1A C1A H1A1 108.6 . . ? C2A C1A H1A1 108.6 . . ? O1A C1A H1A2 108.6 . . ? C2A C1A H1A2 108.6 . . ? H1A1 C1A H1A2 107.5 . . ? C1A C2A C3A 111.1(5) . . ? C1A C2A H2A1 109.4 . . ? C3A C2A H2A1 109.4 . . ? C1A C2A H2A2 109.4 . . ? C3A C2A H2A2 109.4 . . ? H2A1 C2A H2A2 108.0 . . ? C2A C3A H3A1 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C2A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C1B O1B H1B 109.5 . . ? O1B C1B C2B 114.5(4) . . ? O1B C1B H1B1 108.6 . . ? C2B C1B H1B1 108.6 . . ? O1B C1B H1B2 108.6 . . ? C2B C1B H1B2 108.6 . . ? H1B1 C1B H1B2 107.6 . . ? C1B C2B C3B 110.7(5) . . ? C1B C2B H2B1 109.5 . . ? C3B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? C3B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 108.1 . . ? C2B C3B H3B1 109.5 . . ? C2B C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C2B C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 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 C6 C1 C2 C3 1.2(7) . . . . ? C13 C1 C2 C3 178.2(5) . . . . ? C1 C2 C3 C4 0.7(7) . . . . ? C2 C3 C4 C5 -1.8(8) . . . . ? C3 C4 C5 C6 0.8(8) . . . . ? C2 C1 C6 C5 -2.2(7) . . . . ? C13 C1 C6 C5 -179.6(4) . . . . ? C2 C1 C6 C7 177.2(4) . . . . ? C13 C1 C6 C7 -0.2(5) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C4 C5 C6 C7 -178.1(5) . . . . ? C1 C6 C7 C8 -179.3(5) . . . . ? C5 C6 C7 C8 0.0(9) . . . . ? C1 C6 C7 C12 0.6(5) . . . . ? C5 C6 C7 C12 179.9(5) . . . . ? C12 C7 C8 C9 -1.1(8) . . . . ? C6 C7 C8 C9 178.9(5) . . . . ? C7 C8 C9 C10 0.5(9) . . . . ? C8 C9 C10 C11 0.4(9) . . . . ? C9 C10 C11 C12 -0.8(7) . . . . ? C10 C11 C12 C7 0.2(7) . . . . ? C10 C11 C12 C13 -178.0(5) . . . . ? C8 C7 C12 C11 0.7(7) . . . . ? C6 C7 C12 C11 -179.3(4) . . . . ? C8 C7 C12 C13 179.2(4) . . . . ? C6 C7 C12 C13 -0.8(5) . . . . ? C11 C12 C13 O1 62.9(6) . . . . ? C7 C12 C13 O1 -115.5(4) . . . . ? C11 C12 C13 C1 179.0(4) . . . . ? C7 C12 C13 C1 0.6(5) . . . . ? C11 C12 C13 C14 -57.0(6) . . . . ? C7 C12 C13 C14 124.6(4) . . . . ? C2 C1 C13 O1 -61.0(6) . . . . ? C6 C1 C13 O1 116.2(4) . . . . ? C2 C1 C13 C12 -177.5(4) . . . . ? C6 C1 C13 C12 -0.2(5) . . . . ? C2 C1 C13 C14 60.0(6) . . . . ? C6 C1 C13 C14 -122.8(4) . . . . ? O1 C13 C14 C15 -8.4(5) . . . . ? C12 C13 C14 C15 113.1(5) . . . . ? C1 C13 C14 C15 -130.8(4) . . . . ? O1 C13 C14 C19 172.6(4) . . . . ? C12 C13 C14 C19 -65.8(5) . . . . ? C1 C13 C14 C19 50.3(6) . . . . ? C19 C14 C15 C16 0.7(7) . . . . ? C13 C14 C15 C16 -178.3(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? C15 C16 C17 C18 -1.0(7) . . . . ? C16 C17 C18 C19 0.9(7) . . . . ? C15 C14 C19 C18 -0.8(6) . . . . ? C13 C14 C19 C18 178.1(4) . . . . ? C15 C14 C19 C20 176.6(4) . . . . ? C13 C14 C19 C20 -4.4(7) . . . . ? C17 C18 C19 C14 0.0(7) . . . . ? C17 C18 C19 C20 -177.6(4) . . . . ? C14 C19 C20 C25 90.7(6) . . . . ? C18 C19 C20 C25 -91.8(5) . . . . ? C14 C19 C20 C21 -95.1(5) . . . . ? C18 C19 C20 C21 82.4(5) . . . . ? C25 C20 C21 C22 -0.5(7) . . . . ? C19 C20 C21 C22 -174.9(4) . . . . ? C20 C21 C22 C23 0.5(7) . . . . ? C21 C22 C23 C24 -1.3(7) . . . . ? C21 C22 C23 C26 -174.9(4) . . . . ? C22 C23 C24 C25 2.2(7) . . . . ? C26 C23 C24 C25 175.8(4) . . . . ? C21 C20 C25 C24 1.4(6) . . . . ? C19 C20 C25 C24 175.7(4) . . . . ? C23 C24 C25 C20 -2.3(7) . . . . ? C24 C23 C26 C27 -80.2(6) . . . . ? C22 C23 C26 C27 93.3(5) . . . . ? C24 C23 C26 C31 101.8(5) . . . . ? C22 C23 C26 C31 -84.7(6) . . . . ? C31 C26 C27 C28 0.6(7) . . . . ? C23 C26 C27 C28 -177.5(4) . . . . ? C26 C27 C28 C29 -0.3(7) . . . . ? C27 C28 C29 C30 -0.4(7) . . . . ? C28 C29 C30 C31 0.9(7) . . . . ? C29 C30 C31 C26 -0.6(7) . . . . ? C29 C30 C31 C32 -177.5(4) . . . . ? C27 C26 C31 C30 -0.1(6) . . . . ? C23 C26 C31 C30 177.8(4) . . . . ? C27 C26 C31 C32 176.6(4) . . . . ? C23 C26 C31 C32 -5.5(7) . . . . ? C30 C31 C32 O2 -0.3(6) . . . . ? C26 C31 C32 O2 -177.0(4) . . . . ? C30 C31 C32 C33 120.9(4) . . . . ? C26 C31 C32 C33 -55.8(6) . . . . ? C30 C31 C32 C44 -123.6(5) . . . . ? C26 C31 C32 C44 59.7(6) . . . . ? O2 C32 C33 C34 62.1(6) . . . . ? C44 C32 C33 C34 179.0(4) . . . . ? C31 C32 C33 C34 -58.1(6) . . . . ? O2 C32 C33 C38 -116.4(4) . . . . ? C44 C32 C33 C38 0.6(5) . . . . ? C31 C32 C33 C38 123.5(4) . . . . ? C38 C33 C34 C35 0.1(7) . . . . ? C32 C33 C34 C35 -178.2(4) . . . . ? C33 C34 C35 C36 0.2(7) . . . . ? C34 C35 C36 C37 -0.9(8) . . . . ? C35 C36 C37 C38 1.2(8) . . . . ? C34 C33 C38 C37 0.2(7) . . . . ? C32 C33 C38 C37 178.8(4) . . . . ? C34 C33 C38 C39 -179.4(4) . . . . ? C32 C33 C38 C39 -0.9(5) . . . . ? C36 C37 C38 C33 -0.9(7) . . . . ? C36 C37 C38 C39 178.7(5) . . . . ? C33 C38 C39 C40 179.7(5) . . . . ? C37 C38 C39 C40 0.0(9) . . . . ? C33 C38 C39 C44 0.8(5) . . . . ? C37 C38 C39 C44 -178.8(5) . . . . ? C44 C39 C40 C41 0.2(7) . . . . ? C38 C39 C40 C41 -178.5(5) . . . . ? C39 C40 C41 C42 1.3(8) . . . . ? C40 C41 C42 C43 -1.7(8) . . . . ? C41 C42 C43 C44 0.5(8) . . . . ? C42 C43 C44 C39 1.0(7) . . . . ? C42 C43 C44 C32 178.7(5) . . . . ? C40 C39 C44 C43 -1.4(7) . . . . ? C38 C39 C44 C43 177.6(4) . . . . ? C40 C39 C44 C32 -179.5(4) . . . . ? C38 C39 C44 C32 -0.5(5) . . . . ? O2 C32 C44 C43 -61.2(6) . . . . ? C33 C32 C44 C43 -178.0(5) . . . . ? C31 C32 C44 C43 60.9(6) . . . . ? O2 C32 C44 C39 116.7(4) . . . . ? C33 C32 C44 C39 -0.1(5) . . . . ? C31 C32 C44 C39 -121.1(4) . . . . ? O1A C1A C2A C3A 179.1(5) . . . . ? O1B C1B C2B C3B -175.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.70 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.318 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.065 data_klien_10_0m _database_code_depnum_ccdc_archive 'CCDC 900661' #TrackingRef 'Klien_10_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H62 O2, 2(C4 H11 N)' _chemical_formula_sum 'C68 H84 N2 O2' _chemical_formula_weight 961.37 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6049(2) _cell_length_b 11.0553(3) _cell_length_c 13.1571(3) _cell_angle_alpha 106.016(1) _cell_angle_beta 95.625(1) _cell_angle_gamma 93.744(1) _cell_volume 1468.64(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.064 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 27867 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.10 _reflns_number_total 7077 _reflns_number_gt 5633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.4499P] 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 7077 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 O1 O 1.00029(8) 0.31101(8) 0.40123(6) 0.01772(19) Uani 1 1 d . . . H1 H 0.9540 0.3693 0.3990 0.027 Uiso 1 1 calc R . . C1 C 0.85076(11) 0.18747(10) 0.25018(9) 0.0145(2) Uani 1 1 d . . . C2 C 0.75729(11) 0.12048(11) 0.28489(9) 0.0160(2) Uani 1 1 d . . . H2 H 0.7770 0.0907 0.3452 0.019 Uiso 1 1 calc R . . C3 C 0.63378(11) 0.09671(11) 0.23081(9) 0.0168(2) Uani 1 1 d . . . C4 C 0.60973(11) 0.14235(11) 0.14228(10) 0.0182(2) Uani 1 1 d . . . H4 H 0.5262 0.1272 0.1050 0.022 Uiso 1 1 calc R . . C5 C 0.70361(11) 0.20911(11) 0.10683(9) 0.0172(2) Uani 1 1 d . . . H5 H 0.6845 0.2391 0.0466 0.021 Uiso 1 1 calc R . . C6 C 0.82573(11) 0.23097(10) 0.16124(9) 0.0148(2) Uani 1 1 d . . . C7 C 0.94520(11) 0.29093(10) 0.14124(9) 0.0149(2) Uani 1 1 d . . . C8 C 0.97337(11) 0.34471(11) 0.06165(10) 0.0179(2) Uani 1 1 d . . . H8 H 0.9087 0.3487 0.0077 0.022 Uiso 1 1 calc R . . C9 C 1.09798(12) 0.39275(11) 0.06218(10) 0.0193(2) Uani 1 1 d . . . H9 H 1.1175 0.4292 0.0074 0.023 Uiso 1 1 calc R . . C10 C 1.19588(11) 0.38920(11) 0.14084(10) 0.0174(2) Uani 1 1 d . . . C11 C 1.16590(11) 0.33423(10) 0.22026(9) 0.0159(2) Uani 1 1 d . . . H11 H 1.2300 0.3309 0.2749 0.019 Uiso 1 1 calc R . . C12 C 1.04212(11) 0.28455(10) 0.21888(9) 0.0145(2) Uani 1 1 d . . . C13 C 0.99018(10) 0.22210(11) 0.29806(9) 0.0143(2) Uani 1 1 d . . . C14 C 1.05363(10) 0.10524(11) 0.30900(9) 0.0148(2) Uani 1 1 d . . . C15 C 1.09108(11) 0.09473(12) 0.41053(10) 0.0195(2) Uani 1 1 d . . . H15 H 1.0821 0.1627 0.4711 0.023 Uiso 1 1 calc R . . C16 C 1.14122(12) -0.01318(13) 0.42485(10) 0.0227(3) Uani 1 1 d . . . H16 H 1.1657 -0.0185 0.4948 0.027 Uiso 1 1 calc R . . C17 C 1.15563(12) -0.11269(12) 0.33781(11) 0.0226(3) Uani 1 1 d . . . H17 H 1.1900 -0.1866 0.3473 0.027 Uiso 1 1 calc R . . C18 C 1.11925(12) -0.10337(12) 0.23627(10) 0.0201(3) Uani 1 1 d . . . H18 H 1.1292 -0.1718 0.1764 0.024 Uiso 1 1 calc R . . C19 C 1.06850(11) 0.00393(11) 0.21982(9) 0.0158(2) Uani 1 1 d . . . C20 C 1.03232(11) 0.00389(10) 0.10720(9) 0.0152(2) Uani 1 1 d . . . C21 C 1.12216(11) 0.04304(11) 0.04927(9) 0.0165(2) Uani 1 1 d . . . H21 H 1.2065 0.0721 0.0826 0.020 Uiso 1 1 calc R . . C22 C 0.90960(11) -0.04027(11) 0.05605(9) 0.0165(2) Uani 1 1 d . . . H22 H 0.8474 -0.0686 0.0938 0.020 Uiso 1 1 calc R . . C23 C 0.52559(11) 0.02520(12) 0.26635(10) 0.0208(3) Uani 1 1 d . . . C24 C 0.46257(14) -0.08396(13) 0.17267(12) 0.0298(3) Uani 1 1 d . . . H24A H 0.5263 -0.1412 0.1458 0.045 Uiso 1 1 calc R . . H24B H 0.4263 -0.0504 0.1158 0.045 Uiso 1 1 calc R . . H24C H 0.3948 -0.1303 0.1963 0.045 Uiso 1 1 calc R . . C25 C 0.57163(14) -0.02714(17) 0.35774(14) 0.0380(4) Uani 1 1 d . . . H25A H 0.6344 -0.0870 0.3347 0.057 Uiso 1 1 calc R . . H25B H 0.4992 -0.0705 0.3785 0.057 Uiso 1 1 calc R . . H25C H 0.6108 0.0425 0.4187 0.057 Uiso 1 1 calc R . . C26 C 0.42488(13) 0.11646(13) 0.30482(12) 0.0307(3) Uani 1 1 d . . . H26A H 0.3570 0.0722 0.3303 0.046 Uiso 1 1 calc R . . H26B H 0.3887 0.1463 0.2457 0.046 Uiso 1 1 calc R . . H26C H 0.4649 0.1889 0.3630 0.046 Uiso 1 1 calc R . . C27 C 1.33129(12) 0.44226(12) 0.13501(10) 0.0209(3) Uani 1 1 d . . . C28 C 1.42623(12) 0.43555(14) 0.22797(11) 0.0267(3) Uani 1 1 d . . . H28A H 1.3982 0.4827 0.2952 0.040 Uiso 1 1 calc R . . H28B H 1.5104 0.4726 0.2212 0.040 Uiso 1 1 calc R . . H28C H 1.4310 0.3470 0.2271 0.040 Uiso 1 1 calc R . . C29 C 1.37710(14) 0.36538(15) 0.03155(12) 0.0316(3) Uani 1 1 d . . . H29A H 1.4651 0.3962 0.0287 0.047 Uiso 1 1 calc R . . H29B H 1.3224 0.3749 -0.0297 0.047 Uiso 1 1 calc R . . H29C H 1.3731 0.2760 0.0296 0.047 Uiso 1 1 calc R . . C30 C 1.33194(14) 0.58187(13) 0.13650(15) 0.0352(4) Uani 1 1 d . . . H30A H 1.2976 0.6295 0.2005 0.053 Uiso 1 1 calc R . . H30B H 1.2792 0.5883 0.0731 0.053 Uiso 1 1 calc R . . H30C H 1.4194 0.6168 0.1368 0.053 Uiso 1 1 calc R . . N1A N 0.82891(10) 0.49293(10) 0.41371(9) 0.0230(2) Uani 1 1 d . . . H1A H 0.8669(16) 0.5523(16) 0.4727(14) 0.033(4) Uiso 1 1 d . . . C1A C 0.73112(14) 0.37411(14) 0.52382(12) 0.0319(3) Uani 1 1 d . . . H1A1 H 0.7856 0.3057 0.5013 0.048 Uiso 1 1 calc R . . H1A2 H 0.6493 0.3391 0.5376 0.048 Uiso 1 1 calc R . . H1A3 H 0.7728 0.4359 0.5890 0.048 Uiso 1 1 calc R . . C2A C 0.70888(13) 0.43831(13) 0.43674(12) 0.0280(3) Uani 1 1 d . . . H2A1 H 0.6658 0.3760 0.3712 0.034 Uiso 1 1 calc R . . H2A2 H 0.6522 0.5060 0.4590 0.034 Uiso 1 1 calc R . . C3A C 0.80916(13) 0.55377(13) 0.32867(12) 0.0287(3) Uani 1 1 d . . . H3A1 H 0.7489 0.6187 0.3481 0.034 Uiso 1 1 calc R . . H3A2 H 0.7708 0.4899 0.2623 0.034 Uiso 1 1 calc R . . C4A C 0.93282(15) 0.61529(14) 0.30920(12) 0.0331(3) Uani 1 1 d . . . H4A1 H 0.9717 0.6777 0.3751 0.050 Uiso 1 1 calc R . . H4A2 H 0.9157 0.6575 0.2535 0.050 Uiso 1 1 calc R . . H4A3 H 0.9911 0.5505 0.2863 0.050 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 O1 0.0154(4) 0.0204(4) 0.0143(4) 0.0002(3) 0.0006(3) 0.0018(3) C1 0.0124(5) 0.0152(5) 0.0141(5) 0.0010(4) 0.0017(4) 0.0011(4) C2 0.0150(6) 0.0180(5) 0.0141(5) 0.0032(4) 0.0023(4) 0.0002(4) C3 0.0140(6) 0.0169(5) 0.0183(6) 0.0031(4) 0.0030(4) 0.0001(4) C4 0.0121(5) 0.0205(6) 0.0200(6) 0.0039(5) -0.0014(4) 0.0000(4) C5 0.0161(6) 0.0181(5) 0.0171(6) 0.0053(4) -0.0001(4) 0.0013(4) C6 0.0144(5) 0.0133(5) 0.0152(5) 0.0015(4) 0.0026(4) 0.0008(4) C7 0.0141(5) 0.0134(5) 0.0163(5) 0.0022(4) 0.0031(4) 0.0017(4) C8 0.0179(6) 0.0167(5) 0.0196(6) 0.0062(4) 0.0008(4) 0.0024(4) C9 0.0218(6) 0.0174(6) 0.0217(6) 0.0091(5) 0.0064(5) 0.0023(5) C10 0.0156(6) 0.0141(5) 0.0223(6) 0.0036(4) 0.0064(5) 0.0014(4) C11 0.0136(5) 0.0151(5) 0.0179(6) 0.0027(4) 0.0026(4) 0.0013(4) C12 0.0151(5) 0.0129(5) 0.0147(5) 0.0017(4) 0.0034(4) 0.0019(4) C13 0.0110(5) 0.0175(5) 0.0131(5) 0.0026(4) 0.0007(4) -0.0006(4) C14 0.0097(5) 0.0190(5) 0.0166(5) 0.0067(4) 0.0023(4) -0.0006(4) C15 0.0153(6) 0.0279(6) 0.0161(6) 0.0071(5) 0.0028(4) 0.0016(5) C16 0.0172(6) 0.0348(7) 0.0212(6) 0.0168(5) 0.0018(5) 0.0020(5) C17 0.0178(6) 0.0244(6) 0.0304(7) 0.0156(5) 0.0023(5) 0.0027(5) C18 0.0182(6) 0.0189(6) 0.0238(6) 0.0068(5) 0.0024(5) 0.0018(5) C19 0.0117(5) 0.0186(5) 0.0175(6) 0.0066(4) 0.0008(4) -0.0012(4) C20 0.0168(6) 0.0131(5) 0.0148(5) 0.0021(4) 0.0017(4) 0.0038(4) C21 0.0137(5) 0.0164(5) 0.0178(6) 0.0026(4) 0.0007(4) 0.0014(4) C22 0.0161(6) 0.0155(5) 0.0179(6) 0.0039(4) 0.0043(4) 0.0016(4) C23 0.0143(6) 0.0247(6) 0.0233(6) 0.0078(5) 0.0023(5) -0.0033(5) C24 0.0261(7) 0.0241(7) 0.0357(8) 0.0034(6) 0.0077(6) -0.0063(5) C25 0.0223(7) 0.0563(10) 0.0445(9) 0.0322(8) 0.0017(6) -0.0063(7) C26 0.0210(7) 0.0279(7) 0.0406(8) 0.0033(6) 0.0123(6) -0.0017(5) C27 0.0163(6) 0.0195(6) 0.0289(7) 0.0087(5) 0.0076(5) 0.0008(4) C28 0.0146(6) 0.0314(7) 0.0346(7) 0.0101(6) 0.0060(5) -0.0019(5) C29 0.0246(7) 0.0411(8) 0.0323(8) 0.0115(6) 0.0134(6) 0.0061(6) C30 0.0225(7) 0.0235(7) 0.0641(11) 0.0186(7) 0.0111(7) -0.0005(5) N1A 0.0176(5) 0.0215(5) 0.0247(6) -0.0003(4) -0.0014(4) 0.0004(4) C1A 0.0285(7) 0.0349(8) 0.0290(7) 0.0021(6) 0.0089(6) 0.0008(6) C2A 0.0172(6) 0.0270(7) 0.0351(8) 0.0014(6) 0.0020(5) 0.0020(5) C3A 0.0263(7) 0.0238(6) 0.0328(7) 0.0046(6) -0.0022(6) 0.0034(5) C4A 0.0361(8) 0.0255(7) 0.0340(8) 0.0034(6) 0.0049(6) -0.0015(6) _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 O1 C13 1.4288(13) . ? O1 H1 0.8400 . ? C1 C2 1.3853(16) . ? C1 C6 1.3919(16) . ? C1 C13 1.5296(15) . ? C2 C3 1.4001(16) . ? C2 H2 0.9500 . ? C3 C4 1.3998(17) . ? C3 C23 1.5331(16) . ? C4 C5 1.3923(17) . ? C4 H4 0.9500 . ? C5 C6 1.3893(16) . ? C5 H5 0.9500 . ? C6 C7 1.4717(16) . ? C7 C8 1.3859(16) . ? C7 C12 1.3959(16) . ? C8 C9 1.3903(17) . ? C8 H8 0.9500 . ? C9 C10 1.4028(17) . ? C9 H9 0.9500 . ? C10 C11 1.3973(16) . ? C10 C27 1.5324(16) . ? C11 C12 1.3859(16) . ? C11 H11 0.9500 . ? C12 C13 1.5248(15) . ? C13 C14 1.5297(16) . ? C14 C15 1.3941(16) . ? C14 C19 1.4107(16) . ? C15 C16 1.3887(18) . ? C15 H15 0.9500 . ? C16 C17 1.3806(19) . ? C16 H16 0.9500 . ? C17 C18 1.3873(18) . ? C17 H17 0.9500 . ? C18 C19 1.3948(16) . ? C18 H18 0.9500 . ? C19 C20 1.4937(16) . ? C20 C21 1.3952(16) . ? C20 C22 1.3960(16) . ? C21 C22 1.3850(16) 2_755 ? C21 H21 0.9500 . ? C22 C21 1.3850(16) 2_755 ? C22 H22 0.9500 . ? C23 C25 1.5247(19) . ? C23 C24 1.5280(18) . ? C23 C26 1.5426(18) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.5276(19) . ? C27 C29 1.5350(18) . ? C27 C30 1.5376(18) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N1A C3A 1.4615(18) . ? N1A C2A 1.4673(17) . ? N1A H1A 0.905(18) . ? C1A C2A 1.513(2) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.515(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 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 C13 O1 H1 109.5 . . ? C2 C1 C6 121.61(10) . . ? C2 C1 C13 127.49(10) . . ? C6 C1 C13 110.90(10) . . ? C1 C2 C3 119.84(11) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 117.87(11) . . ? C4 C3 C23 119.75(10) . . ? C2 C3 C23 122.37(10) . . ? C5 C4 C3 122.44(11) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C6 C5 C4 118.75(11) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 119.48(11) . . ? C5 C6 C7 131.98(11) . . ? C1 C6 C7 108.49(10) . . ? C8 C7 C12 119.60(11) . . ? C8 C7 C6 131.76(11) . . ? C12 C7 C6 108.61(10) . . ? C7 C8 C9 118.84(11) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 C10 122.21(11) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 118.20(11) . . ? C11 C10 C27 122.66(11) . . ? C9 C10 C27 119.12(11) . . ? C12 C11 C10 119.65(11) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.48(11) . . ? C11 C12 C13 127.69(11) . . ? C7 C12 C13 110.80(10) . . ? O1 C13 C12 110.27(9) . . ? O1 C13 C1 110.77(9) . . ? C12 C13 C1 101.10(9) . . ? O1 C13 C14 108.21(9) . . ? C12 C13 C14 115.19(9) . . ? C1 C13 C14 111.19(9) . . ? C15 C14 C19 118.69(11) . . ? C15 C14 C13 119.04(10) . . ? C19 C14 C13 122.15(10) . . ? C16 C15 C14 121.28(11) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 120.23(11) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.14(11) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 121.71(12) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C18 C19 C14 118.95(11) . . ? C18 C19 C20 117.28(10) . . ? C14 C19 C20 123.77(10) . . ? C21 C20 C22 118.45(10) . . ? C21 C20 C19 120.61(10) . . ? C22 C20 C19 120.89(10) . . ? C22 C21 C20 121.05(11) 2_755 . ? C22 C21 H21 119.5 2_755 . ? C20 C21 H21 119.5 . . ? C21 C22 C20 120.49(11) 2_755 . ? C21 C22 H22 119.8 2_755 . ? C20 C22 H22 119.8 . . ? C25 C23 C24 108.92(12) . . ? C25 C23 C3 112.41(10) . . ? C24 C23 C3 109.93(10) . . ? C25 C23 C26 107.86(12) . . ? C24 C23 C26 108.61(11) . . ? C3 C23 C26 109.03(10) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C10 112.95(10) . . ? C28 C27 C29 107.87(11) . . ? C10 C27 C29 108.90(11) . . ? C28 C27 C30 107.55(11) . . ? C10 C27 C30 109.73(10) . . ? C29 C27 C30 109.80(12) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C3A N1A C2A 112.10(11) . . ? C3A N1A H1A 107.7(11) . . ? C2A N1A H1A 109.5(11) . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? N1A C2A C1A 111.45(11) . . ? N1A C2A H2A1 109.3 . . ? C1A C2A H2A1 109.3 . . ? N1A C2A H2A2 109.3 . . ? C1A C2A H2A2 109.3 . . ? H2A1 C2A H2A2 108.0 . . ? N1A C3A C4A 111.67(12) . . ? N1A C3A H3A1 109.3 . . ? C4A C3A H3A1 109.3 . . ? N1A C3A H3A2 109.3 . . ? C4A C3A H3A2 109.3 . . ? H3A1 C3A H3A2 107.9 . . ? C3A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C3A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 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 C6 C1 C2 C3 -0.87(17) . . . . ? C13 C1 C2 C3 -179.72(10) . . . . ? C1 C2 C3 C4 0.10(17) . . . . ? C1 C2 C3 C23 -178.90(10) . . . . ? C2 C3 C4 C5 0.26(18) . . . . ? C23 C3 C4 C5 179.29(11) . . . . ? C3 C4 C5 C6 0.13(18) . . . . ? C4 C5 C6 C1 -0.88(17) . . . . ? C4 C5 C6 C7 176.25(11) . . . . ? C2 C1 C6 C5 1.27(17) . . . . ? C13 C1 C6 C5 -179.71(10) . . . . ? C2 C1 C6 C7 -176.48(10) . . . . ? C13 C1 C6 C7 2.54(13) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? C1 C6 C7 C8 177.47(12) . . . . ? C5 C6 C7 C12 -177.91(12) . . . . ? C1 C6 C7 C12 -0.54(13) . . . . ? C12 C7 C8 C9 -0.88(17) . . . . ? C6 C7 C8 C9 -178.71(11) . . . . ? C7 C8 C9 C10 -0.35(18) . . . . ? C8 C9 C10 C11 0.58(18) . . . . ? C8 C9 C10 C27 179.06(11) . . . . ? C9 C10 C11 C12 0.43(16) . . . . ? C27 C10 C11 C12 -178.00(10) . . . . ? C10 C11 C12 C7 -1.68(17) . . . . ? C10 C11 C12 C13 -179.45(10) . . . . ? C8 C7 C12 C11 1.92(17) . . . . ? C6 C7 C12 C11 -179.79(10) . . . . ? C8 C7 C12 C13 -179.97(10) . . . . ? C6 C7 C12 C13 -1.68(12) . . . . ? C11 C12 C13 O1 63.71(14) . . . . ? C7 C12 C13 O1 -114.26(10) . . . . ? C11 C12 C13 C1 -179.06(11) . . . . ? C7 C12 C13 C1 2.98(12) . . . . ? C11 C12 C13 C14 -59.10(15) . . . . ? C7 C12 C13 C14 122.94(10) . . . . ? C2 C1 C13 O1 -67.50(14) . . . . ? C6 C1 C13 O1 113.55(10) . . . . ? C2 C1 C13 C12 175.63(11) . . . . ? C6 C1 C13 C12 -3.33(12) . . . . ? C2 C1 C13 C14 52.85(15) . . . . ? C6 C1 C13 C14 -126.10(10) . . . . ? O1 C13 C14 C15 9.11(14) . . . . ? C12 C13 C14 C15 133.01(11) . . . . ? C1 C13 C14 C15 -112.75(11) . . . . ? O1 C13 C14 C19 -174.90(10) . . . . ? C12 C13 C14 C19 -50.99(14) . . . . ? C1 C13 C14 C19 63.25(13) . . . . ? C19 C14 C15 C16 -0.51(17) . . . . ? C13 C14 C15 C16 175.63(11) . . . . ? C14 C15 C16 C17 0.35(18) . . . . ? C15 C16 C17 C18 -0.09(19) . . . . ? C16 C17 C18 C19 0.01(19) . . . . ? C17 C18 C19 C14 -0.17(18) . . . . ? C17 C18 C19 C20 -179.90(11) . . . . ? C15 C14 C19 C18 0.42(16) . . . . ? C13 C14 C19 C18 -175.59(10) . . . . ? C15 C14 C19 C20 -179.87(11) . . . . ? C13 C14 C19 C20 4.12(17) . . . . ? C18 C19 C20 C21 -86.46(14) . . . . ? C14 C19 C20 C21 93.82(14) . . . . ? C18 C19 C20 C22 90.79(14) . . . . ? C14 C19 C20 C22 -88.93(14) . . . . ? C22 C20 C21 C22 1.00(18) . . . 2_755 ? C19 C20 C21 C22 178.32(11) . . . 2_755 ? C21 C20 C22 C21 -1.00(18) . . . 2_755 ? C19 C20 C22 C21 -178.30(11) . . . 2_755 ? C4 C3 C23 C25 175.05(12) . . . . ? C2 C3 C23 C25 -5.97(17) . . . . ? C4 C3 C23 C24 53.55(15) . . . . ? C2 C3 C23 C24 -127.47(12) . . . . ? C4 C3 C23 C26 -65.41(15) . . . . ? C2 C3 C23 C26 113.58(13) . . . . ? C11 C10 C27 C28 -3.44(16) . . . . ? C9 C10 C27 C28 178.15(11) . . . . ? C11 C10 C27 C29 116.37(13) . . . . ? C9 C10 C27 C29 -62.04(14) . . . . ? C11 C10 C27 C30 -123.41(13) . . . . ? C9 C10 C27 C30 58.18(15) . . . . ? C3A N1A C2A C1A 179.19(11) . . . . ? C2A N1A C3A C4A 177.24(11) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.10 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.419 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044 data_klien_14_0m _database_code_depnum_ccdc_archive 'CCDC 900662' #TrackingRef 'Klien_14_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H30 O2, 2(C4 H10 O)' _chemical_formula_sum 'C52 H50 O4' _chemical_formula_weight 738.92 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9750(2) _cell_length_b 10.0343(2) _cell_length_c 12.5415(3) _cell_angle_alpha 93.415(1) _cell_angle_beta 100.351(1) _cell_angle_gamma 110.989(1) _cell_volume 1027.87(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9936 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 34.55 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 394 _exptl_absorpt_coefficient_mu 0.074 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 24430 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 29.10 _reflns_number_total 5518 _reflns_number_gt 4662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.7634P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5518 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O1 O 0.95972(13) 0.03301(12) 0.36411(8) 0.0222(2) Uani 1 1 d . . . H1 H 0.9493 0.0843 0.4155 0.033 Uiso 1 1 calc R . . C1 C 0.83938(17) -0.09308(14) 0.18353(11) 0.0172(3) Uani 1 1 d . . . C2 C 0.96291(18) -0.10019(16) 0.13465(13) 0.0222(3) Uani 1 1 d . . . H2 H 1.0689 -0.0264 0.1536 0.027 Uiso 1 1 calc R . . C3 C 0.9284(2) -0.21854(17) 0.05672(14) 0.0273(3) Uani 1 1 d . . . H3 H 1.0113 -0.2251 0.0216 0.033 Uiso 1 1 calc R . . C4 C 0.7734(2) -0.32674(16) 0.03017(14) 0.0270(3) Uani 1 1 d . . . H4 H 0.7514 -0.4059 -0.0238 0.032 Uiso 1 1 calc R . . C5 C 0.65024(19) -0.32112(15) 0.08116(13) 0.0231(3) Uani 1 1 d . . . H5 H 0.5452 -0.3963 0.0637 0.028 Uiso 1 1 calc R . . C6 C 0.68399(17) -0.20308(14) 0.15822(12) 0.0180(3) Uani 1 1 d . . . C7 C 0.57903(17) -0.16383(14) 0.22061(11) 0.0175(3) Uani 1 1 d . . . C8 C 0.41540(18) -0.23444(16) 0.22219(13) 0.0227(3) Uani 1 1 d . . . H8 H 0.3529 -0.3249 0.1787 0.027 Uiso 1 1 calc R . . C9 C 0.34447(19) -0.16993(17) 0.28880(13) 0.0258(3) Uani 1 1 d . . . H9 H 0.2324 -0.2166 0.2904 0.031 Uiso 1 1 calc R . . C10 C 0.43610(19) -0.03798(17) 0.35293(13) 0.0248(3) Uani 1 1 d . . . H10 H 0.3863 0.0039 0.3986 0.030 Uiso 1 1 calc R . . C11 C 0.60074(18) 0.03375(16) 0.35093(11) 0.0207(3) Uani 1 1 d . . . H11 H 0.6633 0.1241 0.3946 0.025 Uiso 1 1 calc R . . C12 C 0.67038(16) -0.02968(14) 0.28399(11) 0.0167(3) Uani 1 1 d . . . C13 C 0.84549(16) 0.02655(14) 0.26673(11) 0.0160(3) Uani 1 1 d . . . C14 C 0.89588(15) 0.17461(14) 0.22638(11) 0.0153(2) Uani 1 1 d . . . C15 C 1.04492(16) 0.28235(15) 0.27866(12) 0.0191(3) Uani 1 1 d . . . H15 H 1.1147 0.2609 0.3356 0.023 Uiso 1 1 calc R . . C16 C 1.09311(17) 0.42048(15) 0.24886(12) 0.0217(3) Uani 1 1 d . . . H16 H 1.1952 0.4920 0.2853 0.026 Uiso 1 1 calc R . . C17 C 0.99330(18) 0.45381(15) 0.16669(13) 0.0222(3) Uani 1 1 d . . . H17 H 1.0245 0.5487 0.1475 0.027 Uiso 1 1 calc R . . C18 C 0.84638(17) 0.34682(15) 0.11225(12) 0.0199(3) Uani 1 1 d . . . H18 H 0.7779 0.3695 0.0552 0.024 Uiso 1 1 calc R . . C19 C 0.79699(15) 0.20661(14) 0.13942(11) 0.0152(2) Uani 1 1 d . . . C20 C 0.64322(16) 0.09775(14) 0.06973(10) 0.0146(2) Uani 1 1 d . . . C21 C 0.49070(16) 0.09508(14) 0.08129(11) 0.0160(3) Uani 1 1 d . . . H21 H 0.4836 0.1604 0.1364 0.019 Uiso 1 1 calc R . . C22 C 0.65096(16) 0.00237(14) -0.01286(11) 0.0162(3) Uani 1 1 d . . . H22 H 0.7543 0.0042 -0.0223 0.019 Uiso 1 1 calc R . . O1A O 1.03776(16) 0.81716(12) 0.44708(10) 0.0301(3) Uani 1 1 d . . . H1A H 0.9955 0.8610 0.4038 0.045 Uiso 1 1 calc R . . C1A C 0.9543(3) 0.6677(2) 0.4170(3) 0.0667(9) Uani 1 1 d . . . H1A1 H 0.9989 0.6187 0.4733 0.080 Uiso 1 1 calc R . . H1A2 H 0.9803 0.6406 0.3474 0.080 Uiso 1 1 calc R . . C2A C 0.7755(2) 0.61015(18) 0.40284(14) 0.0298(3) Uani 1 1 d . . . H2A1 H 0.7307 0.6593 0.3468 0.036 Uiso 1 1 calc R . . H2A2 H 0.7492 0.6363 0.4725 0.036 Uiso 1 1 calc R . . C3A C 0.6890(3) 0.4521(2) 0.3704(3) 0.0640(8) Uani 1 1 d . . . H3A1 H 0.7200 0.4259 0.3026 0.077 Uiso 1 1 calc R . . H3A2 H 0.7315 0.4037 0.4280 0.077 Uiso 1 1 calc R . . C4A C 0.5112(3) 0.3913(3) 0.3513(3) 0.0629(8) Uani 1 1 d . . . H4A1 H 0.4764 0.4227 0.4148 0.094 Uiso 1 1 calc R . . H4A2 H 0.4725 0.2859 0.3402 0.094 Uiso 1 1 calc R . . H4A3 H 0.4650 0.4245 0.2861 0.094 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 O1 0.0233(5) 0.0248(5) 0.0164(5) 0.0020(4) -0.0023(4) 0.0097(4) C1 0.0198(6) 0.0135(6) 0.0179(6) 0.0035(5) 0.0033(5) 0.0058(5) C2 0.0210(6) 0.0176(6) 0.0286(7) 0.0042(6) 0.0073(6) 0.0067(5) C3 0.0312(8) 0.0196(7) 0.0358(9) 0.0040(6) 0.0157(7) 0.0110(6) C4 0.0356(8) 0.0154(7) 0.0310(8) -0.0003(6) 0.0121(7) 0.0088(6) C5 0.0268(7) 0.0125(6) 0.0271(7) 0.0012(5) 0.0067(6) 0.0037(5) C6 0.0204(6) 0.0128(6) 0.0199(6) 0.0038(5) 0.0044(5) 0.0049(5) C7 0.0194(6) 0.0134(6) 0.0175(6) 0.0037(5) 0.0038(5) 0.0032(5) C8 0.0211(7) 0.0170(6) 0.0244(7) 0.0029(5) 0.0056(5) 0.0001(5) C9 0.0207(7) 0.0252(7) 0.0290(8) 0.0059(6) 0.0103(6) 0.0029(6) C10 0.0254(7) 0.0272(8) 0.0228(7) 0.0043(6) 0.0108(6) 0.0081(6) C11 0.0240(7) 0.0196(7) 0.0164(6) 0.0022(5) 0.0052(5) 0.0053(5) C12 0.0178(6) 0.0152(6) 0.0147(6) 0.0039(5) 0.0025(5) 0.0034(5) C13 0.0160(6) 0.0144(6) 0.0147(6) 0.0018(5) 0.0004(5) 0.0035(5) C14 0.0147(6) 0.0125(6) 0.0154(6) 0.0000(5) 0.0021(5) 0.0023(5) C15 0.0152(6) 0.0178(6) 0.0191(6) 0.0006(5) -0.0004(5) 0.0022(5) C16 0.0171(6) 0.0160(6) 0.0237(7) -0.0017(5) 0.0016(5) -0.0014(5) C17 0.0241(7) 0.0122(6) 0.0247(7) 0.0012(5) 0.0039(6) 0.0009(5) C18 0.0207(6) 0.0152(6) 0.0198(6) 0.0019(5) 0.0003(5) 0.0041(5) C19 0.0145(5) 0.0133(6) 0.0148(6) -0.0008(5) 0.0018(5) 0.0026(5) C20 0.0152(6) 0.0118(5) 0.0134(6) 0.0014(4) -0.0001(4) 0.0026(5) C21 0.0177(6) 0.0140(6) 0.0148(6) 0.0000(5) 0.0021(5) 0.0051(5) C22 0.0143(6) 0.0158(6) 0.0170(6) 0.0015(5) 0.0022(5) 0.0044(5) O1A 0.0382(6) 0.0182(5) 0.0334(6) 0.0014(5) 0.0079(5) 0.0101(5) C1A 0.0366(11) 0.0174(9) 0.146(3) -0.0130(12) 0.0365(14) 0.0052(8) C2A 0.0319(8) 0.0278(8) 0.0284(8) -0.0022(6) 0.0009(6) 0.0134(7) C3A 0.0361(11) 0.0256(10) 0.127(3) -0.0086(12) 0.0268(13) 0.0070(8) C4A 0.0322(10) 0.0464(13) 0.095(2) -0.0245(13) 0.0055(11) 0.0062(9) _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 O1 C13 1.4282(16) . ? O1 H1 0.8400 . ? C1 C2 1.3806(19) . ? C1 C6 1.4002(19) . ? C1 C13 1.5217(18) . ? C2 C3 1.397(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 H4 0.9500 . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 C7 1.4658(19) . ? C7 C8 1.3877(19) . ? C7 C12 1.4014(19) . ? C8 C9 1.394(2) . ? C8 H8 0.9500 . ? C9 C10 1.390(2) . ? C9 H9 0.9500 . ? C10 C11 1.398(2) . ? C10 H10 0.9500 . ? C11 C12 1.3821(19) . ? C11 H11 0.9500 . ? C12 C13 1.5287(19) . ? C13 C14 1.5357(18) . ? C14 C15 1.3973(18) . ? C14 C19 1.4065(18) . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 C17 1.378(2) . ? C16 H16 0.9500 . ? C17 C18 1.3902(19) . ? C17 H17 0.9500 . ? C18 C19 1.3987(19) . ? C18 H18 0.9500 . ? C19 C20 1.4949(17) . ? C20 C21 1.3933(18) . ? C20 C22 1.3961(18) . ? C21 C22 1.3879(18) 2_655 ? C21 H21 0.9500 . ? C22 C21 1.3879(18) 2_655 ? C22 H22 0.9500 . ? O1A C1A 1.407(2) . ? O1A H1A 0.8400 . ? C1A C2A 1.470(3) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.487(3) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.457(3) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 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 C13 O1 H1 109.5 . . ? C2 C1 C6 121.23(13) . . ? C2 C1 C13 128.00(13) . . ? C6 C1 C13 110.77(12) . . ? C1 C2 C3 118.40(14) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.46(14) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 121.11(14) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 118.54(14) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 120.24(13) . . ? C5 C6 C7 131.05(13) . . ? C1 C6 C7 108.65(12) . . ? C8 C7 C12 120.50(13) . . ? C8 C7 C6 130.84(13) . . ? C12 C7 C6 108.63(12) . . ? C7 C8 C9 118.69(14) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 120.67(14) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.72(14) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.53(14) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C7 120.89(13) . . ? C11 C12 C13 128.61(13) . . ? C7 C12 C13 110.51(12) . . ? O1 C13 C1 107.98(11) . . ? O1 C13 C12 111.34(11) . . ? C1 C13 C12 101.44(10) . . ? O1 C13 C14 109.34(11) . . ? C1 C13 C14 113.20(11) . . ? C12 C13 C14 113.27(11) . . ? C15 C14 C19 118.60(12) . . ? C15 C14 C13 118.84(12) . . ? C19 C14 C13 122.55(11) . . ? C16 C15 C14 121.25(13) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 120.24(13) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.13(13) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 121.58(13) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C18 C19 C14 119.10(12) . . ? C18 C19 C20 116.89(12) . . ? C14 C19 C20 123.97(12) . . ? C21 C20 C22 118.84(12) . . ? C21 C20 C19 120.97(12) . . ? C22 C20 C19 120.08(12) . . ? C22 C21 C20 120.43(12) 2_655 . ? C22 C21 H21 119.8 2_655 . ? C20 C21 H21 119.8 . . ? C21 C22 C20 120.72(12) 2_655 . ? C21 C22 H22 119.6 2_655 . ? C20 C22 H22 119.6 . . ? C1A O1A H1A 109.5 . . ? O1A C1A C2A 117.56(16) . . ? O1A C1A H1A1 107.9 . . ? C2A C1A H1A1 107.9 . . ? O1A C1A H1A2 107.9 . . ? C2A C1A H1A2 107.9 . . ? H1A1 C1A H1A2 107.2 . . ? C1A C2A C3A 116.92(16) . . ? C1A C2A H2A1 108.1 . . ? C3A C2A H2A1 108.1 . . ? C1A C2A H2A2 108.1 . . ? C3A C2A H2A2 108.1 . . ? H2A1 C2A H2A2 107.3 . . ? C4A C3A C2A 118.68(19) . . ? C4A C3A H3A1 107.6 . . ? C2A C3A H3A1 107.6 . . ? C4A C3A H3A2 107.6 . . ? C2A C3A H3A2 107.6 . . ? H3A1 C3A H3A2 107.1 . . ? C3A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C3A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 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 C6 C1 C2 C3 1.6(2) . . . . ? C13 C1 C2 C3 -177.54(14) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C4 C5 C6 C7 176.62(15) . . . . ? C2 C1 C6 C5 -1.2(2) . . . . ? C13 C1 C6 C5 178.04(13) . . . . ? C2 C1 C6 C7 -178.73(13) . . . . ? C13 C1 C6 C7 0.56(15) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C1 C6 C7 C8 178.26(14) . . . . ? C5 C6 C7 C12 -177.06(15) . . . . ? C1 C6 C7 C12 0.06(16) . . . . ? C12 C7 C8 C9 -0.6(2) . . . . ? C6 C7 C8 C9 -178.65(14) . . . . ? C7 C8 C9 C10 -0.4(2) . . . . ? C8 C9 C10 C11 0.8(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C10 C11 C12 C7 -0.9(2) . . . . ? C10 C11 C12 C13 179.56(13) . . . . ? C8 C7 C12 C11 1.3(2) . . . . ? C6 C7 C12 C11 179.73(12) . . . . ? C8 C7 C12 C13 -179.07(12) . . . . ? C6 C7 C12 C13 -0.65(15) . . . . ? C2 C1 C13 O1 -64.53(18) . . . . ? C6 C1 C13 O1 116.24(12) . . . . ? C2 C1 C13 C12 178.34(14) . . . . ? C6 C1 C13 C12 -0.89(14) . . . . ? C2 C1 C13 C14 56.66(18) . . . . ? C6 C1 C13 C14 -122.57(12) . . . . ? C11 C12 C13 O1 65.85(18) . . . . ? C7 C12 C13 O1 -113.73(13) . . . . ? C11 C12 C13 C1 -179.50(14) . . . . ? C7 C12 C13 C1 0.92(14) . . . . ? C11 C12 C13 C14 -57.87(18) . . . . ? C7 C12 C13 C14 122.55(12) . . . . ? O1 C13 C14 C15 6.88(17) . . . . ? C1 C13 C14 C15 -113.54(14) . . . . ? C12 C13 C14 C15 131.69(13) . . . . ? O1 C13 C14 C19 -172.45(12) . . . . ? C1 C13 C14 C19 67.14(16) . . . . ? C12 C13 C14 C19 -47.64(17) . . . . ? C19 C14 C15 C16 2.4(2) . . . . ? C13 C14 C15 C16 -176.94(12) . . . . ? C14 C15 C16 C17 0.2(2) . . . . ? C15 C16 C17 C18 -1.7(2) . . . . ? C16 C17 C18 C19 0.5(2) . . . . ? C17 C18 C19 C14 2.2(2) . . . . ? C17 C18 C19 C20 -175.36(13) . . . . ? C15 C14 C19 C18 -3.57(19) . . . . ? C13 C14 C19 C18 175.76(12) . . . . ? C15 C14 C19 C20 173.79(13) . . . . ? C13 C14 C19 C20 -6.9(2) . . . . ? C18 C19 C20 C21 -76.59(17) . . . . ? C14 C19 C20 C21 106.00(16) . . . . ? C18 C19 C20 C22 99.51(15) . . . . ? C14 C19 C20 C22 -77.91(17) . . . . ? C22 C20 C21 C22 1.0(2) . . . 2_655 ? C19 C20 C21 C22 177.15(12) . . . 2_655 ? C21 C20 C22 C21 -1.0(2) . . . 2_655 ? C19 C20 C22 C21 -177.18(12) . . . 2_655 ? O1A C1A C2A C3A 179.6(2) . . . . ? C1A C2A C3A C4A -177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.532 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.061 data_klien_1_0m _database_code_depnum_ccdc_archive 'CCDC 900663' #TrackingRef 'Klien_1_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H30 O2, 2(C2 H6 O)' _chemical_formula_sum 'C48 H42 O4' _chemical_formula_weight 682.82 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4578(2) _cell_length_b 12.9959(2) _cell_length_c 14.1065(3) _cell_angle_alpha 64.774(1) _cell_angle_beta 80.205(1) _cell_angle_gamma 73.551(1) _cell_volume 1819.47(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9833 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.66 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.078 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 34487 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.40 _reflns_number_total 8134 _reflns_number_gt 6797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.4988P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8134 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 O1 O 0.23865(7) 0.25416(7) 0.14782(6) 0.01984(19) Uani 1 1 d . . . H1 H 0.2938 0.2003 0.1386 0.030 Uiso 1 1 calc R . . C1 C 0.23182(10) 0.11675(10) 0.32826(9) 0.0148(2) Uani 1 1 d . . . C2 C 0.31310(10) 0.01185(10) 0.33890(9) 0.0171(2) Uani 1 1 d . . . H2 H 0.3259 -0.0163 0.2850 0.020 Uiso 1 1 calc R . . C3 C 0.37608(11) -0.05206(10) 0.43072(9) 0.0191(2) Uani 1 1 d . . . H3 H 0.4323 -0.1246 0.4397 0.023 Uiso 1 1 calc R . . C4 C 0.35688(11) -0.00994(10) 0.50912(9) 0.0190(2) Uani 1 1 d . . . H4 H 0.4003 -0.0543 0.5712 0.023 Uiso 1 1 calc R . . C5 C 0.27549(10) 0.09571(10) 0.49813(9) 0.0179(2) Uani 1 1 d . . . H5 H 0.2630 0.1240 0.5519 0.022 Uiso 1 1 calc R . . C6 C 0.21249(10) 0.15955(10) 0.40688(9) 0.0155(2) Uani 1 1 d . . . C7 C 0.12187(10) 0.27193(10) 0.37321(9) 0.0161(2) Uani 1 1 d . . . C8 C 0.06767(11) 0.34578(11) 0.42471(10) 0.0206(2) Uani 1 1 d . . . H8 H 0.0887 0.3268 0.4935 0.025 Uiso 1 1 calc R . . C9 C -0.01794(11) 0.44798(11) 0.37337(11) 0.0240(3) Uani 1 1 d . . . H9 H -0.0554 0.4993 0.4075 0.029 Uiso 1 1 calc R . . C10 C -0.04956(11) 0.47617(11) 0.27295(11) 0.0233(3) Uani 1 1 d . . . H10 H -0.1076 0.5468 0.2389 0.028 Uiso 1 1 calc R . . C11 C 0.00324(11) 0.40143(10) 0.22165(10) 0.0196(2) Uani 1 1 d . . . H11 H -0.0188 0.4200 0.1533 0.023 Uiso 1 1 calc R . . C12 C 0.08844(10) 0.29970(10) 0.27274(9) 0.0161(2) Uani 1 1 d . . . C13 C 0.15709(10) 0.20427(10) 0.23416(9) 0.0152(2) Uani 1 1 d . . . C14 C 0.07030(10) 0.15660(10) 0.20060(9) 0.0154(2) Uani 1 1 d . . . C15 C 0.05929(11) 0.19124(10) 0.09355(9) 0.0188(2) Uani 1 1 d . . . H15 H 0.1075 0.2414 0.0439 0.023 Uiso 1 1 calc R . . C16 C -0.02033(11) 0.15416(11) 0.05795(9) 0.0218(3) Uani 1 1 d . . . H16 H -0.0263 0.1789 -0.0152 0.026 Uiso 1 1 calc R . . C17 C -0.09081(12) 0.08129(12) 0.12921(10) 0.0236(3) Uani 1 1 d . . . H17 H -0.1451 0.0551 0.1055 0.028 Uiso 1 1 calc R . . C18 C -0.08164(11) 0.04650(11) 0.23603(10) 0.0215(3) Uani 1 1 d . . . H18 H -0.1304 -0.0035 0.2848 0.026 Uiso 1 1 calc R . . C19 C -0.00258(10) 0.08317(10) 0.27352(9) 0.0167(2) Uani 1 1 d . . . C20 C -0.00048(10) 0.04119(10) 0.39033(9) 0.0163(2) Uani 1 1 d . . . C21 C -0.06580(10) 0.11200(10) 0.44237(9) 0.0171(2) Uani 1 1 d . . . H21 H -0.1116 0.1885 0.4035 0.021 Uiso 1 1 calc R . . C22 C 0.06443(10) -0.07149(10) 0.44947(9) 0.0175(2) Uani 1 1 d . . . H22 H 0.1083 -0.1211 0.4152 0.021 Uiso 1 1 calc R . . O1A O 0.57294(7) 0.67548(7) 0.07376(6) 0.01731(18) Uani 1 1 d . . . H1A H 0.6388 0.6294 0.0669 0.026 Uiso 1 1 calc R . . C1A C 0.53648(10) 0.52223(10) 0.24006(8) 0.0144(2) Uani 1 1 d . . . C2A C 0.63009(11) 0.42339(10) 0.25755(9) 0.0165(2) Uani 1 1 d . . . H2A H 0.7120 0.4295 0.2367 0.020 Uiso 1 1 calc R . . C3A C 0.60163(11) 0.31400(10) 0.30667(9) 0.0199(2) Uani 1 1 d . . . H3A H 0.6648 0.2448 0.3197 0.024 Uiso 1 1 calc R . . C4A C 0.48148(12) 0.30592(11) 0.33658(9) 0.0212(3) Uani 1 1 d . . . H4A H 0.4636 0.2309 0.3701 0.025 Uiso 1 1 calc R . . C5A C 0.38714(11) 0.40548(11) 0.31837(9) 0.0197(2) Uani 1 1 d . . . H5A H 0.3052 0.3994 0.3389 0.024 Uiso 1 1 calc R . . C6A C 0.41529(10) 0.51412(10) 0.26948(9) 0.0163(2) Uani 1 1 d . . . C7A C 0.33646(10) 0.63253(10) 0.23937(9) 0.0168(2) Uani 1 1 d . . . C8A C 0.21097(11) 0.67068(12) 0.25131(10) 0.0234(3) Uani 1 1 d . . . H8A H 0.1611 0.6161 0.2842 0.028 Uiso 1 1 calc R . . C9A C 0.15976(12) 0.79044(12) 0.21402(11) 0.0271(3) Uani 1 1 d . . . H9A H 0.0740 0.8177 0.2214 0.033 Uiso 1 1 calc R . . C10A C 0.23194(12) 0.87092(11) 0.16612(10) 0.0247(3) Uani 1 1 d . . . H10A H 0.1951 0.9524 0.1414 0.030 Uiso 1 1 calc R . . C11A C 0.35864(11) 0.83271(10) 0.15406(9) 0.0190(2) Uani 1 1 d . . . H11A H 0.4085 0.8873 0.1213 0.023 Uiso 1 1 calc R . . C12A C 0.40923(10) 0.71362(10) 0.19110(8) 0.0156(2) Uani 1 1 d . . . C13A C 0.54270(10) 0.65033(10) 0.18319(8) 0.0143(2) Uani 1 1 d . . . C14A C 0.62978(10) 0.68795(9) 0.22714(9) 0.0142(2) Uani 1 1 d . . . C15A C 0.70434(10) 0.75946(10) 0.15694(9) 0.0164(2) Uani 1 1 d . . . H15A H 0.6995 0.7838 0.0837 0.020 Uiso 1 1 calc R . . C16A C 0.78551(11) 0.79583(10) 0.19178(9) 0.0184(2) Uani 1 1 d . . . H16A H 0.8356 0.8442 0.1426 0.022 Uiso 1 1 calc R . . C17A C 0.79324(11) 0.76149(11) 0.29806(10) 0.0199(2) Uani 1 1 d . . . H17A H 0.8488 0.7858 0.3224 0.024 Uiso 1 1 calc R . . C18A C 0.71917(11) 0.69124(11) 0.36898(9) 0.0197(2) Uani 1 1 d . . . H18A H 0.7243 0.6683 0.4420 0.024 Uiso 1 1 calc R . . C19A C 0.63721(10) 0.65335(10) 0.33565(9) 0.0156(2) Uani 1 1 d . . . C20A C 0.56479(10) 0.57468(10) 0.41912(8) 0.0156(2) Uani 1 1 d . . . C21A C 0.62155(11) 0.45828(10) 0.47613(9) 0.0170(2) Uani 1 1 d . . . H21A H 0.7052 0.4295 0.4604 0.020 Uiso 1 1 calc R . . C22A C 0.44249(11) 0.61635(10) 0.44433(9) 0.0170(2) Uani 1 1 d . . . H22A H 0.4029 0.6959 0.4071 0.020 Uiso 1 1 calc R . . O1B O 0.43166(8) 0.11036(7) 0.08516(7) 0.02102(19) Uani 1 1 d . . . H1B H 0.4395 0.1725 0.0337 0.032 Uiso 1 1 calc R . . C1B C 0.54345(11) 0.05457(11) 0.13753(10) 0.0232(3) Uani 1 1 d . . . H1B1 H 0.6104 0.0405 0.0868 0.028 Uiso 1 1 calc R . . H1B2 H 0.5367 -0.0223 0.1937 0.028 Uiso 1 1 calc R . . C2B C 0.57373(14) 0.12739(15) 0.18460(12) 0.0372(4) Uani 1 1 d . . . H2B1 H 0.5867 0.2011 0.1286 0.056 Uiso 1 1 calc R . . H2B2 H 0.6480 0.0845 0.2231 0.056 Uiso 1 1 calc R . . H2B3 H 0.5062 0.1440 0.2328 0.056 Uiso 1 1 calc R . . O1C O 0.78851(8) 0.54287(8) 1.02740(7) 0.0250(2) Uani 1 1 d . . . H1C H 0.7878 0.5991 0.9685 0.038 Uiso 1 1 calc R . . C1C C 0.79334(14) 0.43915(12) 1.01361(11) 0.0339(3) Uani 1 1 d . . . H1C1 H 0.8134 0.3704 1.0804 0.041 Uiso 1 1 calc R . . H1C2 H 0.8589 0.4303 0.9600 0.041 Uiso 1 1 calc R . . C2C C 0.6746(2) 0.44231(17) 0.97992(14) 0.0546(5) Uani 1 1 d . . . H2C1 H 0.6097 0.4499 1.0333 0.082 Uiso 1 1 calc R . . H2C2 H 0.6811 0.3698 0.9715 0.082 Uiso 1 1 calc R . . H2C3 H 0.6553 0.5093 0.9129 0.082 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 O1 0.0169(4) 0.0188(4) 0.0174(4) -0.0024(3) 0.0039(3) -0.0052(3) C1 0.0122(5) 0.0148(5) 0.0153(5) -0.0025(4) 0.0006(4) -0.0064(4) C2 0.0158(5) 0.0168(6) 0.0170(5) -0.0052(5) 0.0016(4) -0.0051(4) C3 0.0159(5) 0.0145(6) 0.0230(6) -0.0042(5) -0.0017(4) -0.0026(4) C4 0.0167(5) 0.0189(6) 0.0181(6) -0.0020(5) -0.0046(4) -0.0057(5) C5 0.0175(6) 0.0202(6) 0.0174(6) -0.0066(5) -0.0010(4) -0.0078(5) C6 0.0119(5) 0.0154(5) 0.0184(5) -0.0049(4) 0.0005(4) -0.0059(4) C7 0.0125(5) 0.0151(5) 0.0207(6) -0.0055(5) -0.0002(4) -0.0061(4) C8 0.0180(6) 0.0211(6) 0.0257(6) -0.0116(5) -0.0012(5) -0.0057(5) C9 0.0201(6) 0.0215(6) 0.0344(7) -0.0168(6) 0.0001(5) -0.0031(5) C10 0.0178(6) 0.0153(6) 0.0337(7) -0.0077(5) -0.0045(5) -0.0004(5) C11 0.0173(6) 0.0170(6) 0.0212(6) -0.0043(5) -0.0018(4) -0.0043(5) C12 0.0132(5) 0.0147(5) 0.0195(6) -0.0053(4) 0.0020(4) -0.0061(4) C13 0.0144(5) 0.0134(5) 0.0137(5) -0.0019(4) 0.0012(4) -0.0040(4) C14 0.0140(5) 0.0135(5) 0.0156(5) -0.0047(4) -0.0014(4) -0.0001(4) C15 0.0190(6) 0.0172(6) 0.0163(6) -0.0053(5) 0.0002(4) -0.0013(4) C16 0.0238(6) 0.0230(6) 0.0167(6) -0.0092(5) -0.0043(5) 0.0010(5) C17 0.0222(6) 0.0254(7) 0.0274(7) -0.0141(5) -0.0064(5) -0.0036(5) C18 0.0198(6) 0.0211(6) 0.0236(6) -0.0070(5) -0.0012(5) -0.0078(5) C19 0.0153(5) 0.0161(6) 0.0169(5) -0.0058(4) -0.0008(4) -0.0022(4) C20 0.0136(5) 0.0193(6) 0.0154(5) -0.0040(5) 0.0009(4) -0.0088(4) C21 0.0146(5) 0.0162(5) 0.0177(5) -0.0029(4) -0.0004(4) -0.0060(4) C22 0.0155(5) 0.0178(6) 0.0190(6) -0.0068(5) 0.0021(4) -0.0062(4) O1A 0.0205(4) 0.0177(4) 0.0118(4) -0.0053(3) 0.0010(3) -0.0037(3) C1A 0.0182(5) 0.0150(5) 0.0110(5) -0.0054(4) -0.0002(4) -0.0056(4) C2A 0.0178(5) 0.0181(6) 0.0135(5) -0.0060(4) -0.0001(4) -0.0053(4) C3A 0.0235(6) 0.0149(6) 0.0195(6) -0.0062(5) -0.0022(5) -0.0024(5) C4A 0.0275(6) 0.0164(6) 0.0202(6) -0.0054(5) 0.0004(5) -0.0097(5) C5A 0.0200(6) 0.0211(6) 0.0202(6) -0.0085(5) 0.0022(5) -0.0096(5) C6A 0.0174(6) 0.0188(6) 0.0142(5) -0.0078(5) -0.0002(4) -0.0052(4) C7A 0.0178(6) 0.0185(6) 0.0160(5) -0.0088(5) -0.0011(4) -0.0042(4) C8A 0.0178(6) 0.0266(7) 0.0282(7) -0.0138(5) 0.0012(5) -0.0059(5) C9A 0.0164(6) 0.0304(7) 0.0361(7) -0.0183(6) -0.0017(5) 0.0002(5) C10A 0.0242(6) 0.0199(6) 0.0289(7) -0.0120(5) -0.0067(5) 0.0031(5) C11A 0.0222(6) 0.0164(6) 0.0184(6) -0.0073(5) -0.0024(4) -0.0031(5) C12A 0.0168(5) 0.0183(6) 0.0132(5) -0.0082(4) -0.0018(4) -0.0026(4) C13A 0.0168(5) 0.0134(5) 0.0116(5) -0.0041(4) -0.0003(4) -0.0038(4) C14A 0.0142(5) 0.0117(5) 0.0152(5) -0.0052(4) -0.0002(4) -0.0014(4) C15A 0.0170(5) 0.0145(5) 0.0152(5) -0.0044(4) -0.0002(4) -0.0028(4) C16A 0.0168(5) 0.0153(6) 0.0213(6) -0.0055(5) 0.0022(4) -0.0057(4) C17A 0.0194(6) 0.0200(6) 0.0242(6) -0.0108(5) -0.0013(5) -0.0070(5) C18A 0.0226(6) 0.0221(6) 0.0167(6) -0.0092(5) -0.0004(5) -0.0069(5) C19A 0.0166(5) 0.0146(5) 0.0156(5) -0.0066(4) 0.0018(4) -0.0041(4) C20A 0.0200(6) 0.0191(6) 0.0107(5) -0.0069(4) 0.0005(4) -0.0085(5) C21A 0.0172(5) 0.0203(6) 0.0147(5) -0.0080(5) 0.0004(4) -0.0051(4) C22A 0.0214(6) 0.0170(6) 0.0133(5) -0.0064(4) -0.0005(4) -0.0054(4) O1B 0.0211(4) 0.0181(4) 0.0197(4) -0.0034(3) -0.0035(3) -0.0037(3) C1B 0.0183(6) 0.0239(6) 0.0200(6) -0.0053(5) -0.0011(5) 0.0004(5) C2B 0.0279(7) 0.0546(10) 0.0361(8) -0.0212(7) -0.0021(6) -0.0155(7) O1C 0.0285(5) 0.0182(4) 0.0222(5) -0.0046(4) 0.0001(4) -0.0026(4) C1C 0.0464(9) 0.0204(7) 0.0293(7) -0.0111(6) 0.0089(6) -0.0044(6) C2C 0.0875(15) 0.0510(11) 0.0395(9) -0.0202(8) -0.0182(9) -0.0256(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4352(13) . ? O1 H1 0.8400 . ? C1 C2 1.3793(16) . ? C1 C6 1.4003(16) . ? C1 C13 1.5288(16) . ? C2 C3 1.3963(17) . ? C2 H2 0.9500 . ? C3 C4 1.3915(17) . ? C3 H3 0.9500 . ? C4 C5 1.3862(17) . ? C4 H4 0.9500 . ? C5 C6 1.3903(16) . ? C5 H5 0.9500 . ? C6 C7 1.4678(16) . ? C7 C8 1.3921(17) . ? C7 C12 1.3985(16) . ? C8 C9 1.3910(18) . ? C8 H8 0.9500 . ? C9 C10 1.3890(19) . ? C9 H9 0.9500 . ? C10 C11 1.3965(18) . ? C10 H10 0.9500 . ? C11 C12 1.3844(16) . ? C11 H11 0.9500 . ? C12 C13 1.5265(16) . ? C13 C14 1.5349(16) . ? C14 C15 1.3973(16) . ? C14 C19 1.4101(16) . ? C15 C16 1.3884(17) . ? C15 H15 0.9500 . ? C16 C17 1.3802(18) . ? C16 H16 0.9500 . ? C17 C18 1.3900(18) . ? C17 H17 0.9500 . ? C18 C19 1.3963(16) . ? C18 H18 0.9500 . ? C19 C20 1.5011(16) . ? C21 C22 1.3871(16) 2_556 ? C21 C20 1.3945(17) . ? C21 H21 0.9500 . ? C20 C22 1.3951(16) . ? C22 C21 1.3871(16) 2_556 ? C22 H22 0.9500 . ? O1A C13A 1.4360(13) . ? O1A H1A 0.8400 . ? C1A C2A 1.3787(16) . ? C1A C6A 1.4004(16) . ? C1A C13A 1.5263(15) . ? C2A C3A 1.3977(17) . ? C2A H2A 0.9500 . ? C3A C4A 1.3894(17) . ? C3A H3A 0.9500 . ? C4A C5A 1.3883(17) . ? C4A H4A 0.9500 . ? C5A C6A 1.3876(16) . ? C5A H5A 0.9500 . ? C6A C7A 1.4664(16) . ? C7A C8A 1.3880(17) . ? C7A C12A 1.4008(16) . ? C8A C9A 1.3904(18) . ? C8A H8A 0.9500 . ? C9A C10A 1.3899(19) . ? C9A H9A 0.9500 . ? C10A C11A 1.4010(18) . ? C10A H10A 0.9500 . ? C11A C12A 1.3821(16) . ? C11A H11A 0.9500 . ? C12A C13A 1.5282(16) . ? C13A C14A 1.5376(15) . ? C14A C15A 1.3969(15) . ? C14A C19A 1.4101(15) . ? C15A C16A 1.3901(16) . ? C15A H15A 0.9500 . ? C16A C17A 1.3811(17) . ? C16A H16A 0.9500 . ? C17A C18A 1.3878(17) . ? C17A H17A 0.9500 . ? C18A C19A 1.3982(16) . ? C18A H18A 0.9500 . ? C19A C20A 1.4974(15) . ? C21A C22A 1.3904(16) 2_666 ? C21A C20A 1.3935(16) . ? C21A H21A 0.9500 . ? C20A C22A 1.3958(16) . ? C22A C21A 1.3904(16) 2_666 ? C22A H22A 0.9500 . ? O1B C1B 1.4323(14) . ? O1B H1B 0.8400 . ? C1B C2B 1.502(2) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? O1C C1C 1.4266(16) . ? O1C H1C 0.8400 . ? C1C C2C 1.500(3) . ? C1C H1C1 0.9900 . ? C1C H1C2 0.9900 . ? C2C H2C1 0.9800 . ? C2C H2C2 0.9800 . ? C2C H2C3 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 C13 O1 H1 109.5 . . ? C2 C1 C6 121.34(11) . . ? C2 C1 C13 128.23(10) . . ? C6 C1 C13 110.36(10) . . ? C1 C2 C3 118.50(11) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.31(11) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 121.11(11) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 118.76(11) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 119.98(11) . . ? C5 C6 C7 131.29(11) . . ? C1 C6 C7 108.73(10) . . ? C8 C7 C12 120.17(11) . . ? C8 C7 C6 131.06(11) . . ? C12 C7 C6 108.75(10) . . ? C7 C8 C9 118.63(12) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 121.03(11) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.50(11) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.48(11) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C7 121.17(11) . . ? C11 C12 C13 128.30(11) . . ? C7 C12 C13 110.53(10) . . ? O1 C13 C12 107.37(9) . . ? O1 C13 C1 108.80(9) . . ? C12 C13 C1 101.57(9) . . ? O1 C13 C14 110.72(9) . . ? C12 C13 C14 112.00(9) . . ? C1 C13 C14 115.76(9) . . ? C15 C14 C19 118.69(11) . . ? C15 C14 C13 118.72(10) . . ? C19 C14 C13 122.54(10) . . ? C16 C15 C14 121.60(11) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C17 C16 C15 119.80(11) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 119.42(11) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 121.73(11) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C18 C19 C14 118.76(11) . . ? C18 C19 C20 117.40(10) . . ? C14 C19 C20 123.84(10) . . ? C22 C21 C20 120.47(11) 2_556 . ? C22 C21 H21 119.8 2_556 . ? C20 C21 H21 119.8 . . ? C21 C20 C22 118.62(11) . . ? C21 C20 C19 121.07(11) . . ? C22 C20 C19 120.29(10) . . ? C21 C22 C20 120.91(11) 2_556 . ? C21 C22 H22 119.5 2_556 . ? C20 C22 H22 119.5 . . ? C13A O1A H1A 109.5 . . ? C2A C1A C6A 121.18(10) . . ? C2A C1A C13A 128.48(10) . . ? C6A C1A C13A 110.22(10) . . ? C1A C2A C3A 118.45(11) . . ? C1A C2A H2A 120.8 . . ? C3A C2A H2A 120.8 . . ? C4A C3A C2A 120.38(11) . . ? C4A C3A H3A 119.8 . . ? C2A C3A H3A 119.8 . . ? C5A C4A C3A 121.17(11) . . ? C5A C4A H4A 119.4 . . ? C3A C4A H4A 119.4 . . ? C6A C5A C4A 118.50(11) . . ? C6A C5A H5A 120.7 . . ? C4A C5A H5A 120.7 . . ? C5A C6A C1A 120.32(11) . . ? C5A C6A C7A 130.76(11) . . ? C1A C6A C7A 108.91(10) . . ? C8A C7A C12A 120.29(11) . . ? C8A C7A C6A 131.01(11) . . ? C12A C7A C6A 108.70(10) . . ? C7A C8A C9A 118.58(12) . . ? C7A C8A H8A 120.7 . . ? C9A C8A H8A 120.7 . . ? C10A C9A C8A 121.14(12) . . ? C10A C9A H9A 119.4 . . ? C8A C9A H9A 119.4 . . ? C9A C10A C11A 120.43(12) . . ? C9A C10A H10A 119.8 . . ? C11A C10A H10A 119.8 . . ? C12A C11A C10A 118.28(11) . . ? C12A C11A H11A 120.9 . . ? C10A C11A H11A 120.9 . . ? C11A C12A C7A 121.28(11) . . ? C11A C12A C13A 128.37(11) . . ? C7A C12A C13A 110.28(10) . . ? O1A C13A C1A 108.74(9) . . ? O1A C13A C12A 106.18(9) . . ? C1A C13A C12A 101.74(9) . . ? O1A C13A C14A 110.47(9) . . ? C1A C13A C14A 115.55(9) . . ? C12A C13A C14A 113.47(9) . . ? C15A C14A C19A 118.61(10) . . ? C15A C14A C13A 118.80(10) . . ? C19A C14A C13A 122.59(10) . . ? C16A C15A C14A 121.55(10) . . ? C16A C15A H15A 119.2 . . ? C14A C15A H15A 119.2 . . ? C17A C16A C15A 119.86(11) . . ? C17A C16A H16A 120.1 . . ? C15A C16A H16A 120.1 . . ? C16A C17A C18A 119.42(11) . . ? C16A C17A H17A 120.3 . . ? C18A C17A H17A 120.3 . . ? C17A C18A C19A 121.66(11) . . ? C17A C18A H18A 119.2 . . ? C19A C18A H18A 119.2 . . ? C18A C19A C14A 118.90(10) . . ? C18A C19A C20A 117.07(10) . . ? C14A C19A C20A 124.00(10) . . ? C22A C21A C20A 120.93(11) 2_666 . ? C22A C21A H21A 119.5 2_666 . ? C20A C21A H21A 119.5 . . ? C21A C20A C22A 118.92(10) . . ? C21A C20A C19A 119.52(10) . . ? C22A C20A C19A 121.51(10) . . ? C21A C22A C20A 120.14(11) 2_666 . ? C21A C22A H22A 119.9 2_666 . ? C20A C22A H22A 119.9 . . ? C1B O1B H1B 109.5 . . ? O1B C1B C2B 111.87(11) . . ? O1B C1B H1B1 109.2 . . ? C2B C1B H1B1 109.2 . . ? O1B C1B H1B2 109.2 . . ? C2B C1B H1B2 109.2 . . ? H1B1 C1B H1B2 107.9 . . ? C1B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C1C O1C H1C 109.5 . . ? O1C C1C C2C 111.71(13) . . ? O1C C1C H1C1 109.3 . . ? C2C C1C H1C1 109.3 . . ? O1C C1C H1C2 109.3 . . ? C2C C1C H1C2 109.3 . . ? H1C1 C1C H1C2 107.9 . . ? C1C C2C H2C1 109.5 . . ? C1C C2C H2C2 109.5 . . ? H2C1 C2C H2C2 109.5 . . ? C1C C2C H2C3 109.5 . . ? H2C1 C2C H2C3 109.5 . . ? H2C2 C2C H2C3 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 C6 C1 C2 C3 0.34(16) . . . . ? C13 C1 C2 C3 177.00(10) . . . . ? C1 C2 C3 C4 -0.18(17) . . . . ? C2 C3 C4 C5 -0.06(17) . . . . ? C3 C4 C5 C6 0.13(17) . . . . ? C4 C5 C6 C1 0.03(16) . . . . ? C4 C5 C6 C7 179.77(11) . . . . ? C2 C1 C6 C5 -0.27(16) . . . . ? C13 C1 C6 C5 -177.47(10) . . . . ? C2 C1 C6 C7 179.94(10) . . . . ? C13 C1 C6 C7 2.73(12) . . . . ? C5 C6 C7 C8 -3.4(2) . . . . ? C1 C6 C7 C8 176.40(11) . . . . ? C5 C6 C7 C12 178.47(11) . . . . ? C1 C6 C7 C12 -1.77(12) . . . . ? C12 C7 C8 C9 -1.23(17) . . . . ? C6 C7 C8 C9 -179.22(11) . . . . ? C7 C8 C9 C10 0.25(18) . . . . ? C8 C9 C10 C11 0.72(19) . . . . ? C9 C10 C11 C12 -0.69(18) . . . . ? C10 C11 C12 C7 -0.30(17) . . . . ? C10 C11 C12 C13 179.20(11) . . . . ? C8 C7 C12 C11 1.27(17) . . . . ? C6 C7 C12 C11 179.68(10) . . . . ? C8 C7 C12 C13 -178.31(10) . . . . ? C6 C7 C12 C13 0.10(12) . . . . ? C11 C12 C13 O1 67.76(14) . . . . ? C7 C12 C13 O1 -112.70(10) . . . . ? C11 C12 C13 C1 -178.12(11) . . . . ? C7 C12 C13 C1 1.42(11) . . . . ? C11 C12 C13 C14 -53.99(15) . . . . ? C7 C12 C13 C14 125.55(10) . . . . ? C2 C1 C13 O1 -66.44(14) . . . . ? C6 C1 C13 O1 110.53(10) . . . . ? C2 C1 C13 C12 -179.49(11) . . . . ? C6 C1 C13 C12 -2.53(11) . . . . ? C2 C1 C13 C14 58.96(15) . . . . ? C6 C1 C13 C14 -124.08(10) . . . . ? O1 C13 C14 C15 -15.50(14) . . . . ? C12 C13 C14 C15 104.30(12) . . . . ? C1 C13 C14 C15 -139.90(11) . . . . ? O1 C13 C14 C19 167.25(10) . . . . ? C12 C13 C14 C19 -72.94(13) . . . . ? C1 C13 C14 C19 42.85(14) . . . . ? C19 C14 C15 C16 -0.66(17) . . . . ? C13 C14 C15 C16 -178.01(10) . . . . ? C14 C15 C16 C17 -0.02(18) . . . . ? C15 C16 C17 C18 0.42(19) . . . . ? C16 C17 C18 C19 -0.13(19) . . . . ? C17 C18 C19 C14 -0.55(18) . . . . ? C17 C18 C19 C20 179.55(11) . . . . ? C15 C14 C19 C18 0.92(17) . . . . ? C13 C14 C19 C18 178.17(10) . . . . ? C15 C14 C19 C20 -179.18(11) . . . . ? C13 C14 C19 C20 -1.93(17) . . . . ? C22 C21 C20 C22 0.99(18) 2_556 . . . ? C22 C21 C20 C19 179.09(10) 2_556 . . . ? C18 C19 C20 C21 -98.69(13) . . . . ? C14 C19 C20 C21 81.41(15) . . . . ? C18 C19 C20 C22 79.38(14) . . . . ? C14 C19 C20 C22 -100.52(14) . . . . ? C21 C20 C22 C21 -0.99(18) . . . 2_556 ? C19 C20 C22 C21 -179.11(10) . . . 2_556 ? C6A C1A C2A C3A -0.72(16) . . . . ? C13A C1A C2A C3A -176.33(10) . . . . ? C1A C2A C3A C4A 0.23(17) . . . . ? C2A C3A C4A C5A 0.18(18) . . . . ? C3A C4A C5A C6A -0.10(18) . . . . ? C4A C5A C6A C1A -0.38(17) . . . . ? C4A C5A C6A C7A 179.22(11) . . . . ? C2A C1A C6A C5A 0.81(17) . . . . ? C13A C1A C6A C5A 177.15(10) . . . . ? C2A C1A C6A C7A -178.88(10) . . . . ? C13A C1A C6A C7A -2.53(12) . . . . ? C5A C6A C7A C8A 0.4(2) . . . . ? C1A C6A C7A C8A -179.99(12) . . . . ? C5A C6A C7A C12A -179.49(12) . . . . ? C1A C6A C7A C12A 0.15(13) . . . . ? C12A C7A C8A C9A 0.27(18) . . . . ? C6A C7A C8A C9A -179.57(12) . . . . ? C7A C8A C9A C10A -0.27(19) . . . . ? C8A C9A C10A C11A 0.2(2) . . . . ? C9A C10A C11A C12A -0.11(18) . . . . ? C10A C11A C12A C7A 0.12(17) . . . . ? C10A C11A C12A C13A 176.99(11) . . . . ? C8A C7A C12A C11A -0.21(17) . . . . ? C6A C7A C12A C11A 179.67(10) . . . . ? C8A C7A C12A C13A -177.59(10) . . . . ? C6A C7A C12A C13A 2.29(12) . . . . ? C2A C1A C13A O1A 67.89(14) . . . . ? C6A C1A C13A O1A -108.11(10) . . . . ? C2A C1A C13A C12A 179.67(11) . . . . ? C6A C1A C13A C12A 3.66(11) . . . . ? C2A C1A C13A C14A -56.95(15) . . . . ? C6A C1A C13A C14A 127.04(10) . . . . ? C11A C12A C13A O1A -67.02(14) . . . . ? C7A C12A C13A O1A 110.13(10) . . . . ? C11A C12A C13A C1A 179.28(11) . . . . ? C7A C12A C13A C1A -3.57(11) . . . . ? C11A C12A C13A C14A 54.50(15) . . . . ? C7A C12A C13A C14A -128.35(10) . . . . ? O1A C13A C14A C15A 13.00(14) . . . . ? C1A C13A C14A C15A 136.95(10) . . . . ? C12A C13A C14A C15A -106.09(11) . . . . ? O1A C13A C14A C19A -167.15(10) . . . . ? C1A C13A C14A C19A -43.20(14) . . . . ? C12A C13A C14A C19A 73.76(13) . . . . ? C19A C14A C15A C16A 0.56(17) . . . . ? C13A C14A C15A C16A -179.59(10) . . . . ? C14A C15A C16A C17A -0.25(17) . . . . ? C15A C16A C17A C18A -0.28(18) . . . . ? C16A C17A C18A C19A 0.50(19) . . . . ? C17A C18A C19A C14A -0.19(18) . . . . ? C17A C18A C19A C20A 178.06(11) . . . . ? C15A C14A C19A C18A -0.33(16) . . . . ? C13A C14A C19A C18A 179.82(10) . . . . ? C15A C14A C19A C20A -178.45(10) . . . . ? C13A C14A C19A C20A 1.70(17) . . . . ? C22A C21A C20A C22A 1.19(18) 2_666 . . . ? C22A C21A C20A C19A 178.60(10) 2_666 . . . ? C18A C19A C20A C21A -74.02(14) . . . . ? C14A C19A C20A C21A 104.13(13) . . . . ? C18A C19A C20A C22A 103.32(13) . . . . ? C14A C19A C20A C22A -78.53(15) . . . . ? C21A C20A C22A C21A -1.18(18) . . . 2_666 ? C19A C20A C22A C21A -178.54(10) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.362 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.042 data_klien_8_0m _database_code_depnum_ccdc_archive 'CCDC 900665' #TrackingRef 'Klien_8_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H62 O2, C4 H10 O' _chemical_formula_sum 'C64 H72 O3' _chemical_formula_weight 889.22 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1123(3) _cell_length_b 15.8485(4) _cell_length_c 27.3301(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.504(1) _cell_angle_gamma 90.00 _cell_volume 5174.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5657 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.94 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.068 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 43815 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.29 _reflns_number_total 11535 _reflns_number_gt 6968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.0458P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11535 _refine_ls_number_parameters 620 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1 O -0.03791(9) 0.47737(9) 0.25819(5) 0.0209(3) Uani 1 1 d . . . H1 H -0.0816 0.4688 0.2314 0.031 Uiso 1 1 calc R . . O2 O 0.80927(9) 0.44290(8) 0.16921(5) 0.0184(3) Uani 1 1 d . . . H2 H 0.8234 0.3924 0.1632 0.028 Uiso 1 1 calc R . . C1 C 0.09726(14) 0.53646(12) 0.21197(7) 0.0177(4) Uani 1 1 d . . . C2 C 0.05124(14) 0.54052(13) 0.16209(7) 0.0196(4) Uani 1 1 d . . . H2A H 0.0041 0.4964 0.1473 0.024 Uiso 1 1 calc R . . C3 C 0.07417(15) 0.60934(13) 0.13361(7) 0.0230(5) Uani 1 1 d . . . C4 C 0.14510(16) 0.67219(13) 0.15693(8) 0.0274(5) Uani 1 1 d . . . H4 H 0.1621 0.7191 0.1378 0.033 Uiso 1 1 calc R . . C5 C 0.19155(15) 0.66884(13) 0.20667(8) 0.0256(5) Uani 1 1 d . . . H5 H 0.2392 0.7127 0.2215 0.031 Uiso 1 1 calc R . . C6 C 0.16710(14) 0.60009(12) 0.23441(7) 0.0193(4) Uani 1 1 d . . . C7 C 0.20070(14) 0.57949(12) 0.28713(7) 0.0203(4) Uani 1 1 d . . . C8 C 0.27246(15) 0.61886(13) 0.32487(8) 0.0263(5) Uani 1 1 d . . . H8 H 0.3086 0.6701 0.3189 0.032 Uiso 1 1 calc R . . C9 C 0.29091(16) 0.58212(13) 0.37180(8) 0.0274(5) Uani 1 1 d . . . H9 H 0.3411 0.6088 0.3975 0.033 Uiso 1 1 calc R . . C10 C 0.23832(15) 0.50741(13) 0.38241(7) 0.0223(5) Uani 1 1 d . . . C11 C 0.16594(14) 0.46881(13) 0.34356(7) 0.0202(4) Uani 1 1 d . . . H11 H 0.1288 0.4179 0.3494 0.024 Uiso 1 1 calc R . . C12 C 0.14854(14) 0.50446(12) 0.29695(7) 0.0184(4) Uani 1 1 d . . . C13 C 0.07580(14) 0.47066(12) 0.24992(7) 0.0181(4) Uani 1 1 d . . . C14 C 0.10460(14) 0.37903(12) 0.23881(6) 0.0173(4) Uani 1 1 d . . . C15 C 0.03534(15) 0.31474(13) 0.25086(7) 0.0226(5) Uani 1 1 d . . . H15 H -0.0280 0.3290 0.2655 0.027 Uiso 1 1 calc R . . C16 C 0.05611(15) 0.23082(13) 0.24206(7) 0.0254(5) Uani 1 1 d . . . H16 H 0.0078 0.1883 0.2510 0.031 Uiso 1 1 calc R . . C17 C 0.14680(16) 0.20877(13) 0.22033(7) 0.0265(5) Uani 1 1 d . . . H17 H 0.1606 0.1513 0.2134 0.032 Uiso 1 1 calc R . . C18 C 0.21722(15) 0.27147(13) 0.20873(7) 0.0234(5) Uani 1 1 d . . . H18 H 0.2799 0.2562 0.1939 0.028 Uiso 1 1 calc R . . C19 C 0.19964(14) 0.35629(12) 0.21803(6) 0.0178(4) Uani 1 1 d . . . C20 C 0.28543(14) 0.41697(12) 0.20564(7) 0.0174(4) Uani 1 1 d . . . C21 C 0.36141(14) 0.45546(12) 0.24249(7) 0.0178(4) Uani 1 1 d . . . H21 H 0.3554 0.4468 0.2763 0.021 Uiso 1 1 calc R . . C22 C 0.44589(14) 0.50630(12) 0.23041(7) 0.0188(4) Uani 1 1 d . . . H22 H 0.4952 0.5339 0.2561 0.023 Uiso 1 1 calc R . . C23 C 0.45972(14) 0.51762(12) 0.18147(7) 0.0166(4) Uani 1 1 d . . . C24 C 0.38305(14) 0.48005(12) 0.14437(7) 0.0192(4) Uani 1 1 d . . . H24 H 0.3897 0.4884 0.1106 0.023 Uiso 1 1 calc R . . C25 C 0.29723(14) 0.43071(12) 0.15626(7) 0.0194(4) Uani 1 1 d . . . H25 H 0.2454 0.4057 0.1304 0.023 Uiso 1 1 calc R . . C26 C 0.55294(14) 0.57285(12) 0.16993(6) 0.0156(4) Uani 1 1 d . . . C27 C 0.53021(15) 0.65861(12) 0.16382(7) 0.0194(4) Uani 1 1 d . . . H27 H 0.4561 0.6781 0.1640 0.023 Uiso 1 1 calc R . . C28 C 0.61262(15) 0.71626(13) 0.15756(7) 0.0218(4) Uani 1 1 d . . . H28 H 0.5954 0.7746 0.1537 0.026 Uiso 1 1 calc R . . C29 C 0.71996(15) 0.68791(12) 0.15693(7) 0.0206(4) Uani 1 1 d . . . H29 H 0.7776 0.7270 0.1534 0.025 Uiso 1 1 calc R . . C30 C 0.74382(14) 0.60283(12) 0.16144(6) 0.0185(4) Uani 1 1 d . . . H30 H 0.8177 0.5840 0.1601 0.022 Uiso 1 1 calc R . . C31 C 0.66220(14) 0.54411(12) 0.16784(6) 0.0150(4) Uani 1 1 d . . . C32 C 0.69329(13) 0.45060(12) 0.17422(6) 0.0154(4) Uani 1 1 d . . . C33 C 0.67374(13) 0.41573(12) 0.22405(7) 0.0162(4) Uani 1 1 d . . . C34 C 0.71328(14) 0.44734(12) 0.27047(7) 0.0176(4) Uani 1 1 d . . . H34 H 0.7616 0.4950 0.2741 0.021 Uiso 1 1 calc R . . C35 C 0.68233(14) 0.40924(12) 0.31269(7) 0.0194(4) Uani 1 1 d . . . C36 C 0.61135(14) 0.33994(12) 0.30528(7) 0.0202(4) Uani 1 1 d . . . H36 H 0.5890 0.3138 0.3334 0.024 Uiso 1 1 calc R . . C37 C 0.57153(14) 0.30714(12) 0.25840(7) 0.0193(4) Uani 1 1 d . . . H37 H 0.5234 0.2594 0.2547 0.023 Uiso 1 1 calc R . . C38 C 0.60330(14) 0.34530(12) 0.21737(7) 0.0168(4) Uani 1 1 d . . . C39 C 0.57209(14) 0.32950(12) 0.16404(7) 0.0172(4) Uani 1 1 d . . . C40 C 0.50418(14) 0.26851(12) 0.13775(7) 0.0188(4) Uani 1 1 d . . . H40 H 0.4694 0.2264 0.1547 0.023 Uiso 1 1 calc R . . C41 C 0.48806(14) 0.27006(12) 0.08642(7) 0.0211(4) Uani 1 1 d . . . H41 H 0.4419 0.2282 0.0685 0.025 Uiso 1 1 calc R . . C42 C 0.53727(15) 0.33106(12) 0.05993(7) 0.0202(4) Uani 1 1 d . . . C43 C 0.60437(14) 0.39228(12) 0.08678(7) 0.0178(4) Uani 1 1 d . . . H43 H 0.6387 0.4347 0.0699 0.021 Uiso 1 1 calc R . . C44 C 0.62088(13) 0.39114(11) 0.13815(7) 0.0156(4) Uani 1 1 d . . . C45 C 0.02714(17) 0.61717(14) 0.07829(7) 0.0294(5) Uani 1 1 d . . . C46 C -0.03890(19) 0.69982(15) 0.06847(8) 0.0397(6) Uani 1 1 d . . . H46A H -0.1007 0.7001 0.0875 0.060 Uiso 1 1 calc R . . H46B H -0.0690 0.7044 0.0330 0.060 Uiso 1 1 calc R . . H46C H 0.0108 0.7477 0.0786 0.060 Uiso 1 1 calc R . . C47 C -0.05157(18) 0.54441(15) 0.05966(8) 0.0357(6) Uani 1 1 d . . . H47A H -0.0103 0.4910 0.0639 0.054 Uiso 1 1 calc R . . H47B H -0.0815 0.5528 0.0244 0.054 Uiso 1 1 calc R . . H47C H -0.1134 0.5427 0.0787 0.054 Uiso 1 1 calc R . . C48 C 0.12527(18) 0.61746(16) 0.04908(8) 0.0405(6) Uani 1 1 d . . . H48A H 0.1740 0.6658 0.0594 0.061 Uiso 1 1 calc R . . H48B H 0.0962 0.6217 0.0135 0.061 Uiso 1 1 calc R . . H48C H 0.1681 0.5651 0.0557 0.061 Uiso 1 1 calc R . . C49 C 0.25556(16) 0.46956(13) 0.43464(7) 0.0255(5) Uani 1 1 d . . . C50 C 0.1567(2) 0.4918(2) 0.45935(9) 0.0692(10) Uani 1 1 d . . . H50A H 0.1665 0.4665 0.4925 0.104 Uiso 1 1 calc R . . H50B H 0.0879 0.4701 0.4394 0.104 Uiso 1 1 calc R . . H50C H 0.1515 0.5533 0.4622 0.104 Uiso 1 1 calc R . . C51 C 0.3618(2) 0.5007(2) 0.46693(9) 0.0633(9) Uani 1 1 d . . . H51A H 0.3711 0.4723 0.4992 0.095 Uiso 1 1 calc R . . H51B H 0.3567 0.5618 0.4718 0.095 Uiso 1 1 calc R . . H51C H 0.4263 0.4882 0.4507 0.095 Uiso 1 1 calc R . . C52 C 0.2633(3) 0.37402(17) 0.43265(10) 0.0787(11) Uani 1 1 d . . . H52A H 0.3241 0.3579 0.4149 0.118 Uiso 1 1 calc R . . H52B H 0.1924 0.3511 0.4153 0.118 Uiso 1 1 calc R . . H52C H 0.2783 0.3514 0.4665 0.118 Uiso 1 1 calc R . . C53 C 0.72205(16) 0.44742(13) 0.36402(7) 0.0253(5) Uani 1 1 d . . . C54 C 0.66620(19) 0.53408(14) 0.36618(8) 0.0375(6) Uani 1 1 d . . . H54A H 0.6880 0.5709 0.3406 0.056 Uiso 1 1 calc R . . H54B H 0.6903 0.5593 0.3989 0.056 Uiso 1 1 calc R . . H54C H 0.5847 0.5272 0.3604 0.056 Uiso 1 1 calc R . . C55 C 0.6904(2) 0.39256(15) 0.40565(8) 0.0406(6) Uani 1 1 d . . . H55A H 0.6087 0.3890 0.4021 0.061 Uiso 1 1 calc R . . H55B H 0.7206 0.4177 0.4378 0.061 Uiso 1 1 calc R . . H55C H 0.7215 0.3358 0.4036 0.061 Uiso 1 1 calc R . . C56 C 0.84995(17) 0.45783(16) 0.37278(8) 0.0398(6) Uani 1 1 d . . . H56A H 0.8853 0.4024 0.3716 0.060 Uiso 1 1 calc R . . H56B H 0.8745 0.4835 0.4054 0.060 Uiso 1 1 calc R . . H56C H 0.8716 0.4942 0.3470 0.060 Uiso 1 1 calc R . . C57 C 0.51451(15) 0.32860(13) 0.00297(7) 0.0234(5) Uani 1 1 d . . . C58 C 0.58203(17) 0.39456(14) -0.02005(7) 0.0302(5) Uani 1 1 d . . . H58A H 0.5598 0.4511 -0.0109 0.045 Uiso 1 1 calc R . . H58B H 0.5677 0.3887 -0.0562 0.045 Uiso 1 1 calc R . . H58C H 0.6620 0.3863 -0.0078 0.045 Uiso 1 1 calc R . . C59 C 0.54579(18) 0.24182(14) -0.01537(8) 0.0342(5) Uani 1 1 d . . . H59A H 0.5290 0.2402 -0.0517 0.051 Uiso 1 1 calc R . . H59B H 0.5025 0.1981 -0.0017 0.051 Uiso 1 1 calc R . . H59C H 0.6259 0.2317 -0.0045 0.051 Uiso 1 1 calc R . . C60 C 0.38878(16) 0.34511(14) -0.01516(8) 0.0299(5) Uani 1 1 d . . . H60A H 0.3684 0.4003 -0.0032 0.045 Uiso 1 1 calc R . . H60B H 0.3445 0.3011 -0.0023 0.045 Uiso 1 1 calc R . . H60C H 0.3736 0.3444 -0.0515 0.045 Uiso 1 1 calc R . . O1A O 0.86785(13) 0.28979(10) 0.14028(5) 0.0379(4) Uani 1 1 d . . . H1A H 0.8779 0.2459 0.1577 0.057 Uiso 1 1 calc R . . C1A C 0.85294(18) 0.26747(15) 0.08895(8) 0.0371(6) Uani 1 1 d . . . H1A1 H 0.8369 0.3191 0.0686 0.045 Uiso 1 1 calc R . . H1A2 H 0.7875 0.2295 0.0812 0.045 Uiso 1 1 calc R . . C2A C 0.95425(18) 0.22440(15) 0.07517(8) 0.0376(6) Uani 1 1 d . . . H2A1 H 0.9372 0.2070 0.0399 0.045 Uiso 1 1 calc R . . H2A2 H 0.9695 0.1726 0.0954 0.045 Uiso 1 1 calc R . . C3A C 1.05822(17) 0.27827(15) 0.08242(8) 0.0337(5) Uani 1 1 d . . . H3A1 H 1.0706 0.3013 0.1166 0.040 Uiso 1 1 calc R . . H3A2 H 1.0467 0.3265 0.0591 0.040 Uiso 1 1 calc R . . C4A C 1.1620(2) 0.22969(18) 0.07409(9) 0.0522(7) Uani 1 1 d . . . H4A1 H 1.1742 0.1820 0.0972 0.078 Uiso 1 1 calc R . . H4A2 H 1.2272 0.2672 0.0798 0.078 Uiso 1 1 calc R . . H4A3 H 1.1514 0.2086 0.0399 0.078 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 O1 0.0123(6) 0.0301(8) 0.0203(7) -0.0021(6) 0.0027(5) -0.0016(6) O2 0.0131(6) 0.0191(8) 0.0237(7) -0.0015(6) 0.0048(5) 0.0002(5) C1 0.0131(8) 0.0183(11) 0.0228(10) 0.0004(9) 0.0061(7) 0.0033(8) C2 0.0145(9) 0.0219(12) 0.0234(11) -0.0016(9) 0.0061(7) 0.0015(8) C3 0.0172(9) 0.0273(12) 0.0266(11) 0.0062(9) 0.0097(8) 0.0057(8) C4 0.0247(10) 0.0245(12) 0.0352(12) 0.0091(10) 0.0118(9) 0.0018(9) C5 0.0209(10) 0.0206(12) 0.0363(12) 0.0008(10) 0.0074(9) -0.0028(8) C6 0.0144(9) 0.0184(11) 0.0260(11) -0.0008(9) 0.0057(8) 0.0026(8) C7 0.0132(8) 0.0186(11) 0.0294(11) -0.0014(9) 0.0040(8) 0.0005(8) C8 0.0221(10) 0.0212(12) 0.0352(12) -0.0044(10) 0.0035(9) -0.0034(9) C9 0.0229(10) 0.0269(13) 0.0301(12) -0.0099(10) -0.0018(9) -0.0024(9) C10 0.0191(9) 0.0240(12) 0.0240(11) -0.0048(9) 0.0037(8) 0.0022(8) C11 0.0148(9) 0.0208(11) 0.0251(11) -0.0019(9) 0.0037(8) -0.0020(8) C12 0.0120(8) 0.0198(11) 0.0236(10) -0.0028(9) 0.0039(7) 0.0007(8) C13 0.0122(8) 0.0231(12) 0.0196(10) 0.0005(9) 0.0040(7) -0.0008(8) C14 0.0155(9) 0.0199(11) 0.0156(10) 0.0007(8) 0.0003(7) -0.0028(8) C15 0.0183(9) 0.0258(12) 0.0232(11) 0.0033(9) 0.0018(8) -0.0040(8) C16 0.0230(10) 0.0216(12) 0.0307(12) 0.0054(10) 0.0014(8) -0.0070(9) C17 0.0274(10) 0.0172(12) 0.0333(12) -0.0002(9) 0.0004(9) -0.0012(9) C18 0.0217(10) 0.0219(12) 0.0268(11) 0.0012(9) 0.0048(8) 0.0031(8) C19 0.0170(9) 0.0190(11) 0.0166(10) 0.0034(8) 0.0003(7) -0.0010(8) C20 0.0136(8) 0.0144(11) 0.0245(10) 0.0006(8) 0.0045(7) 0.0028(7) C21 0.0155(8) 0.0199(11) 0.0190(10) 0.0015(8) 0.0057(7) 0.0039(8) C22 0.0135(8) 0.0207(11) 0.0218(10) -0.0035(9) 0.0022(7) 0.0028(8) C23 0.0138(8) 0.0137(10) 0.0231(10) 0.0009(8) 0.0054(7) 0.0034(7) C24 0.0174(9) 0.0208(11) 0.0203(10) 0.0032(9) 0.0052(8) 0.0033(8) C25 0.0160(9) 0.0204(11) 0.0211(10) -0.0020(9) 0.0013(7) 0.0012(8) C26 0.0165(9) 0.0167(11) 0.0137(9) -0.0009(8) 0.0030(7) -0.0011(7) C27 0.0184(9) 0.0188(12) 0.0216(10) -0.0015(9) 0.0052(8) 0.0029(8) C28 0.0276(10) 0.0158(11) 0.0225(10) 0.0013(9) 0.0053(8) 0.0000(8) C29 0.0224(9) 0.0214(12) 0.0184(10) 0.0007(9) 0.0042(8) -0.0064(8) C30 0.0150(9) 0.0220(12) 0.0187(10) 0.0007(8) 0.0029(7) -0.0011(8) C31 0.0161(8) 0.0172(11) 0.0119(9) -0.0004(8) 0.0029(7) -0.0027(8) C32 0.0111(8) 0.0176(11) 0.0180(10) -0.0010(8) 0.0039(7) -0.0001(7) C33 0.0111(8) 0.0164(11) 0.0215(10) 0.0017(8) 0.0037(7) 0.0036(7) C34 0.0154(9) 0.0150(11) 0.0225(10) 0.0003(8) 0.0033(7) 0.0002(8) C35 0.0186(9) 0.0185(11) 0.0216(10) 0.0010(9) 0.0048(8) 0.0020(8) C36 0.0218(9) 0.0197(11) 0.0207(10) 0.0033(9) 0.0080(8) 0.0002(8) C37 0.0168(9) 0.0164(11) 0.0255(11) 0.0019(9) 0.0055(8) -0.0014(8) C38 0.0144(8) 0.0142(11) 0.0222(10) -0.0008(8) 0.0043(7) 0.0028(8) C39 0.0122(8) 0.0167(11) 0.0229(10) 0.0010(8) 0.0039(7) 0.0044(7) C40 0.0165(9) 0.0129(11) 0.0271(11) 0.0018(9) 0.0044(8) -0.0002(8) C41 0.0176(9) 0.0184(11) 0.0262(11) -0.0049(9) 0.0010(8) -0.0004(8) C42 0.0172(9) 0.0195(11) 0.0232(10) -0.0025(9) 0.0011(8) 0.0048(8) C43 0.0127(8) 0.0178(11) 0.0230(10) 0.0023(8) 0.0036(7) 0.0022(8) C44 0.0096(8) 0.0153(11) 0.0220(10) -0.0015(8) 0.0029(7) 0.0037(7) C45 0.0293(11) 0.0359(14) 0.0245(11) 0.0064(10) 0.0090(9) 0.0062(10) C46 0.0401(13) 0.0456(16) 0.0341(13) 0.0129(12) 0.0084(10) 0.0155(11) C47 0.0356(12) 0.0481(16) 0.0231(12) 0.0058(11) 0.0039(9) 0.0030(11) C48 0.0384(13) 0.0547(17) 0.0321(13) 0.0086(12) 0.0165(10) 0.0039(12) C49 0.0261(10) 0.0262(13) 0.0217(11) -0.0033(9) -0.0034(8) 0.0020(9) C50 0.0513(16) 0.121(3) 0.0386(15) 0.0309(17) 0.0164(13) 0.0373(17) C51 0.0516(16) 0.098(2) 0.0332(14) 0.0147(15) -0.0150(12) -0.0263(16) C52 0.154(3) 0.0343(17) 0.0341(15) 0.0004(13) -0.0244(17) 0.0153(19) C53 0.0323(11) 0.0265(13) 0.0182(10) -0.0015(9) 0.0072(8) -0.0072(9) C54 0.0503(14) 0.0320(14) 0.0321(13) -0.0096(11) 0.0124(11) -0.0059(11) C55 0.0621(16) 0.0395(15) 0.0218(12) -0.0024(11) 0.0119(11) -0.0136(12) C56 0.0372(12) 0.0579(17) 0.0226(12) -0.0017(11) -0.0007(9) -0.0100(12) C57 0.0253(10) 0.0235(12) 0.0209(10) -0.0046(9) 0.0021(8) 0.0005(9) C58 0.0368(12) 0.0353(14) 0.0190(11) -0.0040(10) 0.0057(9) -0.0027(10) C59 0.0428(13) 0.0313(14) 0.0278(12) -0.0087(10) 0.0036(10) 0.0048(10) C60 0.0314(11) 0.0299(13) 0.0254(11) -0.0009(10) -0.0040(9) 0.0005(10) O1A 0.0438(9) 0.0329(10) 0.0377(9) 0.0001(7) 0.0085(7) 0.0137(8) C1A 0.0332(12) 0.0380(15) 0.0384(14) -0.0078(11) 0.0009(10) 0.0005(11) C2A 0.0461(13) 0.0329(14) 0.0346(13) -0.0058(11) 0.0089(10) 0.0005(11) C3A 0.0326(11) 0.0382(15) 0.0294(12) 0.0004(11) 0.0022(9) 0.0029(10) C4A 0.0485(15) 0.062(2) 0.0455(15) 0.0009(14) 0.0072(12) 0.0243(14) _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 O1 C13 1.436(2) . ? O1 H1 0.8400 . ? O2 C32 1.4390(19) . ? O2 H2 0.8400 . ? C1 C2 1.386(2) . ? C1 C6 1.392(3) . ? C1 C13 1.523(3) . ? C2 C3 1.394(3) . ? C2 H2A 0.9500 . ? C3 C4 1.398(3) . ? C3 C45 1.530(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 C7 1.468(3) . ? C7 C8 1.383(3) . ? C7 C12 1.393(3) . ? C8 C9 1.393(3) . ? C8 H8 0.9500 . ? C9 C10 1.397(3) . ? C9 H9 0.9500 . ? C10 C11 1.401(3) . ? C10 C49 1.531(3) . ? C11 C12 1.377(3) . ? C11 H11 0.9500 . ? C12 C13 1.530(2) . ? C13 C14 1.536(3) . ? C14 C15 1.393(3) . ? C14 C19 1.412(2) . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 C17 1.377(3) . ? C16 H16 0.9500 . ? C17 C18 1.380(3) . ? C17 H17 0.9500 . ? C18 C19 1.391(3) . ? C18 H18 0.9500 . ? C19 C20 1.495(2) . ? C20 C21 1.388(2) . ? C20 C25 1.398(3) . ? C21 C22 1.384(2) . ? C21 H21 0.9500 . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.391(2) . ? C23 C26 1.503(2) . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.391(3) . ? C26 C31 1.410(2) . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.378(3) . ? C28 H28 0.9500 . ? C29 C30 1.380(3) . ? C29 H29 0.9500 . ? C30 C31 1.390(2) . ? C30 H30 0.9500 . ? C31 C32 1.532(3) . ? C32 C33 1.524(2) . ? C32 C44 1.531(2) . ? C33 C34 1.375(2) . ? C33 C38 1.398(2) . ? C34 C35 1.407(3) . ? C34 H34 0.9500 . ? C35 C36 1.389(3) . ? C35 C53 1.531(3) . ? C36 C37 1.393(3) . ? C36 H36 0.9500 . ? C37 C38 1.384(3) . ? C37 H37 0.9500 . ? C38 C39 1.466(2) . ? C39 C40 1.390(3) . ? C39 C44 1.394(3) . ? C40 C41 1.384(3) . ? C40 H40 0.9500 . ? C41 C42 1.399(3) . ? C41 H41 0.9500 . ? C42 C43 1.394(3) . ? C42 C57 1.536(3) . ? C43 C44 1.385(2) . ? C43 H43 0.9500 . ? C45 C47 1.529(3) . ? C45 C46 1.535(3) . ? C45 C48 1.537(3) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.511(3) . ? C49 C51 1.518(3) . ? C49 C52 1.519(3) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 C55 1.530(3) . ? C53 C54 1.536(3) . ? C53 C56 1.537(3) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 C58 1.526(3) . ? C57 C59 1.533(3) . ? C57 C60 1.544(3) . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? O1A C1A 1.429(2) . ? O1A H1A 0.8400 . ? C1A C2A 1.505(3) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.507(3) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.523(3) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 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 C13 O1 H1 109.5 . . ? C32 O2 H2 109.5 . . ? C2 C1 C6 121.06(18) . . ? C2 C1 C13 127.97(17) . . ? C6 C1 C13 110.84(16) . . ? C1 C2 C3 120.03(18) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C2 C3 C4 117.82(18) . . ? C2 C3 C45 122.62(18) . . ? C4 C3 C45 119.54(18) . . ? C5 C4 C3 122.68(19) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C4 C5 C6 118.57(18) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 119.83(17) . . ? C5 C6 C7 131.42(18) . . ? C1 C6 C7 108.73(17) . . ? C8 C7 C12 119.38(18) . . ? C8 C7 C6 132.07(18) . . ? C12 C7 C6 108.53(16) . . ? C7 C8 C9 118.93(19) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C10 122.42(18) . . ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C9 C10 C11 117.54(18) . . ? C9 C10 C49 121.93(17) . . ? C11 C10 C49 120.51(18) . . ? C12 C11 C10 120.18(18) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C7 121.55(17) . . ? C11 C12 C13 127.74(17) . . ? C7 C12 C13 110.70(16) . . ? O1 C13 C1 109.43(14) . . ? O1 C13 C12 106.02(14) . . ? C1 C13 C12 101.13(14) . . ? O1 C13 C14 110.87(14) . . ? C1 C13 C14 116.30(15) . . ? C12 C13 C14 112.28(14) . . ? C15 C14 C19 118.11(18) . . ? C15 C14 C13 118.65(16) . . ? C19 C14 C13 123.22(16) . . ? C16 C15 C14 121.91(18) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C17 C16 C15 120.02(18) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 118.91(19) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C19 122.34(18) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C14 118.67(17) . . ? C18 C19 C20 116.57(16) . . ? C14 C19 C20 124.76(17) . . ? C21 C20 C25 118.08(16) . . ? C21 C20 C19 121.38(16) . . ? C25 C20 C19 120.31(16) . . ? C22 C21 C20 120.69(17) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 121.12(17) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 118.38(16) . . ? C22 C23 C26 119.49(16) . . ? C24 C23 C26 122.07(16) . . ? C25 C24 C23 120.58(17) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C20 121.07(17) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C27 C26 C31 118.63(16) . . ? C27 C26 C23 116.97(15) . . ? C31 C26 C23 124.29(17) . . ? C28 C27 C26 121.81(17) . . ? C28 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? C29 C28 C27 119.15(18) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 120.09(18) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C31 121.51(17) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C30 C31 C26 118.75(17) . . ? C30 C31 C32 119.71(15) . . ? C26 C31 C32 121.51(15) . . ? O2 C32 C33 110.63(13) . . ? O2 C32 C44 110.54(14) . . ? C33 C32 C44 101.26(14) . . ? O2 C32 C31 107.26(14) . . ? C33 C32 C31 112.40(14) . . ? C44 C32 C31 114.73(14) . . ? C34 C33 C38 121.57(17) . . ? C34 C33 C32 127.64(17) . . ? C38 C33 C32 110.74(15) . . ? C33 C34 C35 120.07(17) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 117.53(17) . . ? C36 C35 C53 122.65(17) . . ? C34 C35 C53 119.73(17) . . ? C35 C36 C37 122.76(18) . . ? C35 C36 H36 118.6 . . ? C37 C36 H36 118.6 . . ? C38 C37 C36 118.82(17) . . ? C38 C37 H37 120.6 . . ? C36 C37 H37 120.6 . . ? C37 C38 C33 119.24(17) . . ? C37 C38 C39 132.13(17) . . ? C33 C38 C39 108.53(16) . . ? C40 C39 C44 119.30(17) . . ? C40 C39 C38 131.78(17) . . ? C44 C39 C38 108.89(16) . . ? C41 C40 C39 118.94(18) . . ? C41 C40 H40 120.5 . . ? C39 C40 H40 120.5 . . ? C40 C41 C42 122.41(17) . . ? C40 C41 H41 118.8 . . ? C42 C41 H41 118.8 . . ? C43 C42 C41 118.01(17) . . ? C43 C42 C57 122.87(17) . . ? C41 C42 C57 119.12(17) . . ? C44 C43 C42 119.90(17) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C39 121.43(17) . . ? C43 C44 C32 128.04(17) . . ? C39 C44 C32 110.51(15) . . ? C47 C45 C3 112.20(17) . . ? C47 C45 C46 107.88(17) . . ? C3 C45 C46 109.88(17) . . ? C47 C45 C48 108.81(18) . . ? C3 C45 C48 108.65(16) . . ? C46 C45 C48 109.39(18) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C50 C49 C51 108.8(2) . . ? C50 C49 C52 107.9(2) . . ? C51 C49 C52 107.1(2) . . ? C50 C49 C10 109.22(16) . . ? C51 C49 C10 112.75(18) . . ? C52 C49 C10 110.92(17) . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C49 C51 H51A 109.5 . . ? C49 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C49 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C49 C52 H52A 109.5 . . ? C49 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C49 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C55 C53 C35 112.17(17) . . ? C55 C53 C54 108.25(17) . . ? C35 C53 C54 108.36(16) . . ? C55 C53 C56 108.38(18) . . ? C35 C53 C56 109.96(16) . . ? C54 C53 C56 109.69(18) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C53 C55 H55A 109.5 . . ? C53 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C53 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C53 C56 H56A 109.5 . . ? C53 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C53 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C58 C57 C59 107.57(17) . . ? C58 C57 C42 112.45(16) . . ? C59 C57 C42 109.97(16) . . ? C58 C57 C60 108.61(16) . . ? C59 C57 C60 109.33(16) . . ? C42 C57 C60 108.86(15) . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C57 C59 H59A 109.5 . . ? C57 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C57 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C57 C60 H60A 109.5 . . ? C57 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C57 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C1A O1A H1A 109.5 . . ? O1A C1A C2A 112.44(17) . . ? O1A C1A H1A1 109.1 . . ? C2A C1A H1A1 109.1 . . ? O1A C1A H1A2 109.1 . . ? C2A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.8 . . ? C1A C2A C3A 114.09(19) . . ? C1A C2A H2A1 108.7 . . ? C3A C2A H2A1 108.7 . . ? C1A C2A H2A2 108.7 . . ? C3A C2A H2A2 108.7 . . ? H2A1 C2A H2A2 107.6 . . ? C2A C3A C4A 112.7(2) . . ? C2A C3A H3A1 109.0 . . ? C4A C3A H3A1 109.0 . . ? C2A C3A H3A2 109.0 . . ? C4A C3A H3A2 109.0 . . ? H3A1 C3A H3A2 107.8 . . ? C3A C4A H4A1 109.5 . . ? C3A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C3A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 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 C6 C1 C2 C3 -0.4(3) . . . . ? C13 C1 C2 C3 175.06(16) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C1 C2 C3 C45 179.29(16) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C45 C3 C4 C5 -179.34(17) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C4 C5 C6 C7 -178.51(18) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C13 C1 C6 C5 -176.19(16) . . . . ? C2 C1 C6 C7 178.82(15) . . . . ? C13 C1 C6 C7 2.7(2) . . . . ? C5 C6 C7 C8 -4.8(3) . . . . ? C1 C6 C7 C8 176.47(19) . . . . ? C5 C6 C7 C12 177.02(19) . . . . ? C1 C6 C7 C12 -1.7(2) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? C6 C7 C8 C9 -177.80(19) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C8 C9 C10 C49 -177.45(18) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C49 C10 C11 C12 178.27(17) . . . . ? C10 C11 C12 C7 -0.7(3) . . . . ? C10 C11 C12 C13 178.17(17) . . . . ? C8 C7 C12 C11 0.6(3) . . . . ? C6 C7 C12 C11 179.01(16) . . . . ? C8 C7 C12 C13 -178.40(16) . . . . ? C6 C7 C12 C13 0.0(2) . . . . ? C2 C1 C13 O1 -66.8(2) . . . . ? C6 C1 C13 O1 109.05(16) . . . . ? C2 C1 C13 C12 -178.32(17) . . . . ? C6 C1 C13 C12 -2.52(18) . . . . ? C2 C1 C13 C14 59.8(2) . . . . ? C6 C1 C13 C14 -124.40(16) . . . . ? C11 C12 C13 O1 68.4(2) . . . . ? C7 C12 C13 O1 -112.69(16) . . . . ? C11 C12 C13 C1 -177.46(17) . . . . ? C7 C12 C13 C1 1.46(18) . . . . ? C11 C12 C13 C14 -52.8(2) . . . . ? C7 C12 C13 C14 126.10(16) . . . . ? O1 C13 C14 C15 -16.9(2) . . . . ? C1 C13 C14 C15 -142.76(16) . . . . ? C12 C13 C14 C15 101.45(18) . . . . ? O1 C13 C14 C19 164.69(15) . . . . ? C1 C13 C14 C19 38.9(2) . . . . ? C12 C13 C14 C19 -76.9(2) . . . . ? C19 C14 C15 C16 -1.4(3) . . . . ? C13 C14 C15 C16 -179.85(16) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C15 C16 C17 C18 1.5(3) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C14 -1.8(3) . . . . ? C17 C18 C19 C20 177.35(17) . . . . ? C15 C14 C19 C18 2.6(2) . . . . ? C13 C14 C19 C18 -179.06(16) . . . . ? C15 C14 C19 C20 -176.51(16) . . . . ? C13 C14 C19 C20 1.9(3) . . . . ? C18 C19 C20 C21 -106.8(2) . . . . ? C14 C19 C20 C21 72.2(2) . . . . ? C18 C19 C20 C25 67.6(2) . . . . ? C14 C19 C20 C25 -113.3(2) . . . . ? C25 C20 C21 C22 0.3(3) . . . . ? C19 C20 C21 C22 174.87(17) . . . . ? C20 C21 C22 C23 -2.5(3) . . . . ? C21 C22 C23 C24 3.2(3) . . . . ? C21 C22 C23 C26 -179.59(17) . . . . ? C22 C23 C24 C25 -1.8(3) . . . . ? C26 C23 C24 C25 -178.95(17) . . . . ? C23 C24 C25 C20 -0.3(3) . . . . ? C21 C20 C25 C24 1.0(3) . . . . ? C19 C20 C25 C24 -173.56(17) . . . . ? C22 C23 C26 C27 -87.5(2) . . . . ? C24 C23 C26 C27 89.6(2) . . . . ? C22 C23 C26 C31 88.7(2) . . . . ? C24 C23 C26 C31 -94.2(2) . . . . ? C31 C26 C27 C28 -2.3(3) . . . . ? C23 C26 C27 C28 174.08(16) . . . . ? C26 C27 C28 C29 0.6(3) . . . . ? C27 C28 C29 C30 1.4(3) . . . . ? C28 C29 C30 C31 -1.5(3) . . . . ? C29 C30 C31 C26 -0.3(3) . . . . ? C29 C30 C31 C32 -178.19(16) . . . . ? C27 C26 C31 C30 2.1(3) . . . . ? C23 C26 C31 C30 -173.97(16) . . . . ? C27 C26 C31 C32 -179.97(15) . . . . ? C23 C26 C31 C32 3.9(3) . . . . ? C30 C31 C32 O2 -3.2(2) . . . . ? C26 C31 C32 O2 178.99(15) . . . . ? C30 C31 C32 C33 118.66(17) . . . . ? C26 C31 C32 C33 -59.2(2) . . . . ? C30 C31 C32 C44 -126.36(17) . . . . ? C26 C31 C32 C44 55.8(2) . . . . ? O2 C32 C33 C34 66.7(2) . . . . ? C44 C32 C33 C34 -176.10(17) . . . . ? C31 C32 C33 C34 -53.2(2) . . . . ? O2 C32 C33 C38 -115.67(16) . . . . ? C44 C32 C33 C38 1.54(18) . . . . ? C31 C32 C33 C38 124.45(16) . . . . ? C38 C33 C34 C35 -0.5(3) . . . . ? C32 C33 C34 C35 176.86(16) . . . . ? C33 C34 C35 C36 -0.2(3) . . . . ? C33 C34 C35 C53 -177.01(16) . . . . ? C34 C35 C36 C37 0.6(3) . . . . ? C53 C35 C36 C37 177.38(17) . . . . ? C35 C36 C37 C38 -0.4(3) . . . . ? C36 C37 C38 C33 -0.3(3) . . . . ? C36 C37 C38 C39 -176.28(18) . . . . ? C34 C33 C38 C37 0.8(3) . . . . ? C32 C33 C38 C37 -177.01(15) . . . . ? C34 C33 C38 C39 177.63(16) . . . . ? C32 C33 C38 C39 -0.18(19) . . . . ? C37 C38 C39 C40 -3.3(3) . . . . ? C33 C38 C39 C40 -179.57(18) . . . . ? C37 C38 C39 C44 174.82(18) . . . . ? C33 C38 C39 C44 -1.4(2) . . . . ? C44 C39 C40 C41 0.8(3) . . . . ? C38 C39 C40 C41 178.80(18) . . . . ? C39 C40 C41 C42 -0.3(3) . . . . ? C40 C41 C42 C43 -0.3(3) . . . . ? C40 C41 C42 C57 -179.64(17) . . . . ? C41 C42 C43 C44 0.3(3) . . . . ? C57 C42 C43 C44 179.60(16) . . . . ? C42 C43 C44 C39 0.3(3) . . . . ? C42 C43 C44 C32 178.22(16) . . . . ? C40 C39 C44 C43 -0.9(3) . . . . ? C38 C39 C44 C43 -179.26(15) . . . . ? C40 C39 C44 C32 -179.12(15) . . . . ? C38 C39 C44 C32 2.49(19) . . . . ? O2 C32 C44 C43 -63.3(2) . . . . ? C33 C32 C44 C43 179.45(17) . . . . ? C31 C32 C44 C43 58.2(2) . . . . ? O2 C32 C44 C39 114.84(16) . . . . ? C33 C32 C44 C39 -2.44(18) . . . . ? C31 C32 C44 C39 -123.73(16) . . . . ? C2 C3 C45 C47 3.4(3) . . . . ? C4 C3 C45 C47 -178.10(17) . . . . ? C2 C3 C45 C46 123.4(2) . . . . ? C4 C3 C45 C46 -58.1(2) . . . . ? C2 C3 C45 C48 -117.0(2) . . . . ? C4 C3 C45 C48 61.6(2) . . . . ? C9 C10 C49 C50 100.3(2) . . . . ? C11 C10 C49 C50 -78.0(3) . . . . ? C9 C10 C49 C51 -20.9(3) . . . . ? C11 C10 C49 C51 160.9(2) . . . . ? C9 C10 C49 C52 -141.0(2) . . . . ? C11 C10 C49 C52 40.8(3) . . . . ? C36 C35 C53 C55 9.2(3) . . . . ? C34 C35 C53 C55 -174.14(18) . . . . ? C36 C35 C53 C54 -110.3(2) . . . . ? C34 C35 C53 C54 66.4(2) . . . . ? C36 C35 C53 C56 129.9(2) . . . . ? C34 C35 C53 C56 -53.5(2) . . . . ? C43 C42 C57 C58 5.6(3) . . . . ? C41 C42 C57 C58 -175.12(17) . . . . ? C43 C42 C57 C59 125.39(19) . . . . ? C41 C42 C57 C59 -55.3(2) . . . . ? C43 C42 C57 C60 -114.84(19) . . . . ? C41 C42 C57 C60 64.5(2) . . . . ? O1A C1A C2A C3A -62.3(3) . . . . ? C1A C2A C3A C4A 173.14(19) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.239 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049