# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Junliang Zhang' _publ_contact_author_email JLZHANG@CHEM.ECNU.EDU.CN _publ_section_title ; Rhodium-Catalyzed Tandem Nucleophilic Addition/Bicyclization of Diyne-enones with Alcohols: A Modular Entry to 2,3-Fused Bicyclic Furans. ; _publ_author_name 'Junliang Zhang' # Attachment '2ha.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 761108' #TrackingRef '2ha.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H29 N O8' _chemical_formula_weight 567.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1741(4) _cell_length_b 10.9686(4) _cell_length_c 14.9749(6) _cell_angle_alpha 80.8370(10) _cell_angle_beta 73.1060(10) _cell_angle_gamma 63.5430(10) _cell_volume 1430.68(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yello _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16771 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _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 1.42 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5003 _reflns_number_gt 3333 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.4315P] 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 5003 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.74596(17) 0.54453(16) 0.27974(12) 0.0568(4) Uani 1 1 d . . . O2 O 0.25626(18) 0.76716(17) 0.43240(11) 0.0625(5) Uani 1 1 d . . . O3 O 0.6188(3) 0.2340(3) 0.30980(19) 0.1351(11) Uani 1 1 d . . . O4 O 0.4098(2) 0.31536(19) 0.26343(12) 0.0701(5) Uani 1 1 d . . . O5 O 0.8085(3) 0.1842(3) 0.0697(2) 0.1551(14) Uani 1 1 d . . . O6 O 0.5819(2) 0.25788(19) 0.05179(13) 0.0750(5) Uani 1 1 d . . . O7 O -0.1931(3) 0.6411(2) 0.03403(18) 0.1024(8) Uani 1 1 d . . . O8 O -0.3079(2) 0.8495(2) 0.07064(16) 0.0877(6) Uani 1 1 d . . . N1 N -0.2026(3) 0.7376(3) 0.06970(15) 0.0641(6) Uani 1 1 d . . . C1 C 0.3689(3) 0.9680(3) 0.23370(18) 0.0651(7) Uani 1 1 d . . . H1A H 0.4722 0.9146 0.2129 0.078 Uiso 1 1 calc R . . C2 C 0.2972(4) 1.0804(3) 0.1800(2) 0.0812(9) Uani 1 1 d . . . H2A H 0.3527 1.1021 0.1237 0.097 Uiso 1 1 calc R . . C3 C 0.1462(4) 1.1591(3) 0.2094(3) 0.0907(10) Uani 1 1 d . . . H3A H 0.0981 1.2343 0.1733 0.109 Uiso 1 1 calc R . . C4 C 0.0659(4) 1.1276(3) 0.2916(3) 0.0914(10) Uani 1 1 d . . . H4A H -0.0375 1.1814 0.3116 0.110 Uiso 1 1 calc R . . C5 C 0.1357(3) 1.0164(3) 0.3461(2) 0.0679(7) Uani 1 1 d . . . H5A H 0.0791 0.9967 0.4026 0.082 Uiso 1 1 calc R . . C6 C 0.2888(3) 0.9343(2) 0.31740(16) 0.0500(6) Uani 1 1 d . . . C7 C 0.0258(3) 0.8098(2) 0.18839(18) 0.0587(6) Uani 1 1 d . . . H7A H 0.0261 0.8845 0.2102 0.070 Uiso 1 1 calc R . . C8 C -0.0871(3) 0.8303(3) 0.14693(18) 0.0592(6) Uani 1 1 d . . . H8A H -0.1623 0.9171 0.1407 0.071 Uiso 1 1 calc R . . C9 C -0.0853(3) 0.7189(2) 0.11515(16) 0.0514(6) Uani 1 1 d . . . C10 C 0.0220(3) 0.5895(3) 0.12579(17) 0.0572(6) Uani 1 1 d . . . H10A H 0.0198 0.5153 0.1046 0.069 Uiso 1 1 calc R . . C11 C 0.1331(3) 0.5712(2) 0.16842(17) 0.0559(6) Uani 1 1 d . . . H11A H 0.2052 0.4836 0.1770 0.067 Uiso 1 1 calc R . . C12 C 0.1393(2) 0.6812(2) 0.19880(16) 0.0493(6) Uani 1 1 d . . . C13 C 0.8587(3) 0.6256(3) 0.39698(18) 0.0639(7) Uani 1 1 d . . . H13A H 0.8971 0.5325 0.3890 0.077 Uiso 1 1 calc R . . C14 C 0.9352(3) 0.6746(4) 0.4332(2) 0.0750(8) Uani 1 1 d . . . H14A H 1.0249 0.6146 0.4492 0.090 Uiso 1 1 calc R . . C15 C 0.8801(4) 0.8102(4) 0.4457(2) 0.0798(9) Uani 1 1 d . . . H15A H 0.9317 0.8425 0.4707 0.096 Uiso 1 1 calc R . . C16 C 0.7484(4) 0.8997(3) 0.4214(2) 0.0792(9) Uani 1 1 d . . . H16A H 0.7108 0.9924 0.4302 0.095 Uiso 1 1 calc R . . C17 C 0.6720(3) 0.8516(3) 0.38403(19) 0.0674(7) Uani 1 1 d . . . H17A H 0.5840 0.9127 0.3665 0.081 Uiso 1 1 calc R . . C18 C 0.7248(3) 0.7136(3) 0.37230(16) 0.0540(6) Uani 1 1 d . . . C19 C 0.4051(3) 0.5959(2) 0.21882(16) 0.0465(5) Uani 1 1 d . . . C20 C 0.4858(3) 0.4981(2) 0.13963(16) 0.0495(6) Uani 1 1 d . . . H20A H 0.5305 0.5412 0.0856 0.059 Uiso 1 1 calc R . . H20B H 0.4125 0.4782 0.1227 0.059 Uiso 1 1 calc R . . C21 C 0.6111(3) 0.3635(2) 0.16524(16) 0.0493(6) Uani 1 1 d . . . C22 C 0.7353(3) 0.3940(2) 0.18081(19) 0.0598(7) Uani 1 1 d . . . H22A H 0.8019 0.3165 0.2118 0.072 Uiso 1 1 calc R . . H22B H 0.7953 0.4124 0.1215 0.072 Uiso 1 1 calc R . . C23 C 0.6602(3) 0.5146(2) 0.23960(17) 0.0521(6) Uani 1 1 d . . . C24 C 0.5133(2) 0.6052(2) 0.26214(16) 0.0477(5) Uani 1 1 d . . . C25 C 0.5045(2) 0.6997(2) 0.32365(16) 0.0478(5) Uani 1 1 d . . . C26 C 0.6485(3) 0.6607(2) 0.32984(17) 0.0525(6) Uani 1 1 d . . . C27 C 0.3672(3) 0.8128(2) 0.37744(17) 0.0531(6) Uani 1 1 d . . . H27A H 0.4004 0.8453 0.4203 0.064 Uiso 1 1 calc R . . C28 C 0.3069(4) 0.6660(4) 0.5016(2) 0.0952(10) Uani 1 1 d . . . H28A H 0.2273 0.6392 0.5349 0.143 Uiso 1 1 calc R . . H28B H 0.3339 0.7020 0.5444 0.143 Uiso 1 1 calc R . . H28C H 0.3937 0.5883 0.4724 0.143 Uiso 1 1 calc R . . C29 C 0.2559(3) 0.6723(2) 0.24196(17) 0.0507(6) Uani 1 1 d . . . H29A H 0.2209 0.7277 0.2925 0.061 Uiso 1 1 calc R . . C30 C 0.5489(3) 0.2968(3) 0.25447(18) 0.0617(7) Uani 1 1 d . . . C31 C 0.3366(4) 0.2642(4) 0.3480(2) 0.0954(10) Uani 1 1 d . . . H31A H 0.2356 0.2841 0.3457 0.143 Uiso 1 1 calc R . . H31B H 0.3321 0.3069 0.4006 0.143 Uiso 1 1 calc R . . H31C H 0.3930 0.1674 0.3540 0.143 Uiso 1 1 calc R . . C32 C 0.6791(3) 0.2598(3) 0.08980(19) 0.0626(7) Uani 1 1 d . . . C33 C 0.6324(4) 0.1584(3) -0.01728(19) 0.0745(8) Uani 1 1 d . . . H33A H 0.5479 0.1688 -0.0389 0.112 Uiso 1 1 calc R . . H33B H 0.6756 0.0685 0.0100 0.112 Uiso 1 1 calc R . . H33C H 0.7075 0.1717 -0.0689 0.112 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 0.0438(9) 0.0578(10) 0.0734(11) -0.0087(9) -0.0215(8) -0.0191(8) O2 0.0580(10) 0.0748(11) 0.0565(10) 0.0012(9) -0.0148(8) -0.0305(9) O3 0.130(2) 0.178(3) 0.121(2) 0.087(2) -0.0811(18) -0.085(2) O4 0.0707(12) 0.0801(12) 0.0635(11) 0.0106(9) -0.0167(9) -0.0395(10) O5 0.0815(17) 0.157(3) 0.214(3) -0.126(2) -0.0537(19) 0.0092(17) O6 0.0732(12) 0.0810(13) 0.0744(12) -0.0275(10) -0.0215(10) -0.0258(10) O7 0.0986(17) 0.0981(16) 0.135(2) -0.0301(15) -0.0681(15) -0.0305(13) O8 0.0674(13) 0.0837(14) 0.1170(18) 0.0022(12) -0.0495(12) -0.0220(12) N1 0.0579(14) 0.0728(15) 0.0681(15) -0.0003(12) -0.0265(11) -0.0273(13) C1 0.0596(16) 0.0644(16) 0.0620(17) -0.0064(14) -0.0115(13) -0.0188(13) C2 0.093(2) 0.080(2) 0.0657(19) 0.0063(16) -0.0156(17) -0.0373(19) C3 0.081(2) 0.078(2) 0.094(2) 0.0152(18) -0.035(2) -0.0148(18) C4 0.0609(19) 0.081(2) 0.103(3) 0.0054(19) -0.0232(18) -0.0057(16) C5 0.0530(16) 0.0677(17) 0.0729(18) -0.0074(14) -0.0119(14) -0.0174(14) C6 0.0499(14) 0.0510(13) 0.0532(14) -0.0098(11) -0.0146(11) -0.0211(12) C7 0.0519(15) 0.0519(14) 0.0751(17) -0.0134(12) -0.0210(13) -0.0177(12) C8 0.0504(14) 0.0512(14) 0.0747(17) -0.0035(12) -0.0239(13) -0.0148(12) C9 0.0452(13) 0.0629(15) 0.0504(14) -0.0012(11) -0.0177(11) -0.0233(12) C10 0.0562(15) 0.0560(15) 0.0677(16) -0.0105(12) -0.0213(13) -0.0246(13) C11 0.0495(14) 0.0494(13) 0.0708(16) -0.0058(12) -0.0230(12) -0.0165(11) C12 0.0426(13) 0.0555(14) 0.0519(14) -0.0066(11) -0.0128(11) -0.0202(11) C13 0.0588(16) 0.0779(17) 0.0656(17) 0.0034(14) -0.0227(13) -0.0357(14) C14 0.0698(18) 0.106(2) 0.0721(19) 0.0062(17) -0.0309(15) -0.0518(18) C15 0.089(2) 0.122(3) 0.0649(18) -0.0054(18) -0.0223(16) -0.074(2) C16 0.095(2) 0.084(2) 0.080(2) -0.0139(16) -0.0177(18) -0.0552(19) C17 0.0659(17) 0.0694(18) 0.0771(19) -0.0083(14) -0.0235(14) -0.0322(14) C18 0.0525(14) 0.0701(16) 0.0508(14) -0.0022(12) -0.0156(11) -0.0341(13) C19 0.0482(14) 0.0443(12) 0.0505(13) -0.0019(10) -0.0178(11) -0.0192(11) C20 0.0525(14) 0.0500(13) 0.0483(13) -0.0024(11) -0.0177(11) -0.0203(11) C21 0.0496(13) 0.0467(13) 0.0524(14) -0.0047(11) -0.0176(11) -0.0171(11) C22 0.0491(14) 0.0539(14) 0.0740(17) -0.0110(13) -0.0194(13) -0.0143(12) C23 0.0477(14) 0.0519(14) 0.0626(15) -0.0070(12) -0.0204(12) -0.0204(12) C24 0.0427(13) 0.0490(13) 0.0538(14) -0.0040(11) -0.0170(11) -0.0177(11) C25 0.0445(13) 0.0514(13) 0.0520(14) -0.0055(11) -0.0167(11) -0.0200(11) C26 0.0501(14) 0.0554(14) 0.0560(15) -0.0052(12) -0.0173(12) -0.0221(12) C27 0.0512(14) 0.0591(15) 0.0541(14) -0.0085(12) -0.0154(12) -0.0241(12) C28 0.095(2) 0.113(3) 0.071(2) 0.0290(19) -0.0276(18) -0.044(2) C29 0.0467(14) 0.0530(13) 0.0554(14) -0.0093(11) -0.0169(11) -0.0186(11) C30 0.0736(18) 0.0561(15) 0.0613(16) 0.0071(13) -0.0322(14) -0.0261(14) C31 0.114(3) 0.107(2) 0.072(2) 0.0047(18) 0.0004(19) -0.070(2) C32 0.0533(16) 0.0538(15) 0.0741(18) -0.0106(13) -0.0207(14) -0.0113(13) C33 0.101(2) 0.0673(17) 0.0623(17) -0.0143(14) -0.0192(16) -0.0392(16) _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 C23 1.362(3) . ? O1 C26 1.384(3) . ? O2 C28 1.416(3) . ? O2 C27 1.426(3) . ? O3 C30 1.179(3) . ? O4 C30 1.305(3) . ? O4 C31 1.439(3) . ? O5 C32 1.177(3) . ? O6 C32 1.286(3) . ? O6 C33 1.440(3) . ? O7 N1 1.214(3) . ? O8 N1 1.217(3) . ? N1 C9 1.462(3) . ? C1 C6 1.378(3) . ? C1 C2 1.386(4) . ? C1 H1A 0.9300 . ? C2 C3 1.359(4) . ? C2 H2A 0.9300 . ? C3 C4 1.354(4) . ? C3 H3A 0.9300 . ? C4 C5 1.380(4) . ? C4 H4A 0.9300 . ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 C27 1.519(3) . ? C7 C8 1.376(3) . ? C7 C12 1.389(3) . ? C7 H7A 0.9300 . ? C8 C9 1.371(3) . ? C8 H8A 0.9300 . ? C9 C10 1.372(3) . ? C10 C11 1.380(3) . ? C10 H10A 0.9300 . ? C11 C12 1.388(3) . ? C11 H11A 0.9300 . ? C12 C29 1.468(3) . ? C13 C14 1.379(4) . ? C13 C18 1.390(3) . ? C13 H13A 0.9300 . ? C14 C15 1.358(4) . ? C14 H14A 0.9300 . ? C15 C16 1.374(4) . ? C15 H15A 0.9300 . ? C16 C17 1.381(4) . ? C16 H16A 0.9300 . ? C17 C18 1.384(3) . ? C17 H17A 0.9300 . ? C18 C26 1.466(3) . ? C19 C29 1.334(3) . ? C19 C24 1.476(3) . ? C19 C20 1.512(3) . ? C20 C21 1.542(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C32 1.518(3) . ? C21 C30 1.527(3) . ? C21 C22 1.528(3) . ? C22 C23 1.479(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.351(3) . ? C24 C25 1.450(3) . ? C25 C26 1.359(3) . ? C25 C27 1.503(3) . ? C27 H27A 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 O1 C26 106.42(17) . . ? C28 O2 C27 114.1(2) . . ? C30 O4 C31 117.8(2) . . ? C32 O6 C33 118.8(2) . . ? O7 N1 O8 122.4(2) . . ? O7 N1 C9 119.2(2) . . ? O8 N1 C9 118.3(2) . . ? C6 C1 C2 120.9(3) . . ? C6 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C1 C6 C5 117.8(2) . . ? C1 C6 C27 121.1(2) . . ? C5 C6 C27 121.0(2) . . ? C8 C7 C12 122.2(2) . . ? C8 C7 H7A 118.9 . . ? C12 C7 H7A 118.9 . . ? C9 C8 C7 118.0(2) . . ? C9 C8 H8A 121.0 . . ? C7 C8 H8A 121.0 . . ? C8 C9 C10 122.1(2) . . ? C8 C9 N1 119.3(2) . . ? C10 C9 N1 118.6(2) . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? C10 C11 C12 121.2(2) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C11 C12 C7 117.6(2) . . ? C11 C12 C29 125.1(2) . . ? C7 C12 C29 117.3(2) . . ? C14 C13 C18 120.8(3) . . ? C14 C13 H13A 119.6 . . ? C18 C13 H13A 119.6 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C17 119.9(3) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C17 C18 C13 118.0(2) . . ? C17 C18 C26 121.7(2) . . ? C13 C18 C26 120.1(2) . . ? C29 C19 C24 124.0(2) . . ? C29 C19 C20 124.3(2) . . ? C24 C19 C20 111.53(19) . . ? C19 C20 C21 112.49(18) . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C32 C21 C30 106.39(19) . . ? C32 C21 C22 109.6(2) . . ? C30 C21 C22 108.7(2) . . ? C32 C21 C20 112.15(19) . . ? C30 C21 C20 111.24(19) . . ? C22 C21 C20 108.77(18) . . ? C23 C22 C21 107.51(19) . . ? C23 C22 H22A 110.2 . . ? C21 C22 H22A 110.2 . . ? C23 C22 H22B 110.2 . . ? C21 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C24 C23 O1 111.4(2) . . ? C24 C23 C22 130.1(2) . . ? O1 C23 C22 118.5(2) . . ? C23 C24 C25 105.91(19) . . ? C23 C24 C19 119.1(2) . . ? C25 C24 C19 134.8(2) . . ? C26 C25 C24 106.1(2) . . ? C26 C25 C27 124.5(2) . . ? C24 C25 C27 129.20(19) . . ? C25 C26 O1 110.13(19) . . ? C25 C26 C18 136.1(2) . . ? O1 C26 C18 113.7(2) . . ? O2 C27 C25 112.11(19) . . ? O2 C27 C6 107.44(18) . . ? C25 C27 C6 114.42(19) . . ? O2 C27 H27A 107.5 . . ? C25 C27 H27A 107.5 . . ? C6 C27 H27A 107.5 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C19 C29 C12 129.0(2) . . ? C19 C29 H29A 115.5 . . ? C12 C29 H29A 115.5 . . ? O3 C30 O4 123.0(3) . . ? O3 C30 C21 123.9(3) . . ? O4 C30 C21 113.1(2) . . ? O4 C31 H31A 109.5 . . ? O4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O5 C32 O6 122.6(3) . . ? O5 C32 C21 123.3(3) . . ? O6 C32 C21 114.0(2) . . ? O6 C33 H33A 109.5 . . ? O6 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O6 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 -0.1(5) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? C2 C1 C6 C27 -178.8(2) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C4 C5 C6 C27 179.2(3) . . . . ? C12 C7 C8 C9 -0.1(4) . . . . ? C7 C8 C9 C10 1.8(4) . . . . ? C7 C8 C9 N1 -179.2(2) . . . . ? O7 N1 C9 C8 173.3(2) . . . . ? O8 N1 C9 C8 -8.0(4) . . . . ? O7 N1 C9 C10 -7.6(4) . . . . ? O8 N1 C9 C10 171.0(2) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? N1 C9 C10 C11 179.9(2) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? C10 C11 C12 C7 2.7(4) . . . . ? C10 C11 C12 C29 -177.9(2) . . . . ? C8 C7 C12 C11 -2.1(4) . . . . ? C8 C7 C12 C29 178.5(2) . . . . ? C18 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 -0.2(4) . . . . ? C15 C16 C17 C18 1.3(4) . . . . ? C16 C17 C18 C13 -1.6(4) . . . . ? C16 C17 C18 C26 -177.9(2) . . . . ? C14 C13 C18 C17 0.8(4) . . . . ? C14 C13 C18 C26 177.2(2) . . . . ? C29 C19 C20 C21 -139.4(2) . . . . ? C24 C19 C20 C21 45.5(2) . . . . ? C19 C20 C21 C32 173.4(2) . . . . ? C19 C20 C21 C30 54.4(2) . . . . ? C19 C20 C21 C22 -65.2(2) . . . . ? C32 C21 C22 C23 168.50(19) . . . . ? C30 C21 C22 C23 -75.6(2) . . . . ? C20 C21 C22 C23 45.6(3) . . . . ? C26 O1 C23 C24 -0.4(3) . . . . ? C26 O1 C23 C22 179.8(2) . . . . ? C21 C22 C23 C24 -13.6(4) . . . . ? C21 C22 C23 O1 166.1(2) . . . . ? O1 C23 C24 C25 -1.2(3) . . . . ? C22 C23 C24 C25 178.5(2) . . . . ? O1 C23 C24 C19 175.02(18) . . . . ? C22 C23 C24 C19 -5.2(4) . . . . ? C29 C19 C24 C23 174.0(2) . . . . ? C20 C19 C24 C23 -10.9(3) . . . . ? C29 C19 C24 C25 -11.1(4) . . . . ? C20 C19 C24 C25 164.0(2) . . . . ? C23 C24 C25 C26 2.4(3) . . . . ? C19 C24 C25 C26 -173.0(2) . . . . ? C23 C24 C25 C27 -173.4(2) . . . . ? C19 C24 C25 C27 11.3(4) . . . . ? C24 C25 C26 O1 -2.7(3) . . . . ? C27 C25 C26 O1 173.3(2) . . . . ? C24 C25 C26 C18 174.2(3) . . . . ? C27 C25 C26 C18 -9.8(4) . . . . ? C23 O1 C26 C25 2.0(2) . . . . ? C23 O1 C26 C18 -175.66(19) . . . . ? C17 C18 C26 C25 -28.9(4) . . . . ? C13 C18 C26 C25 154.9(3) . . . . ? C17 C18 C26 O1 147.8(2) . . . . ? C13 C18 C26 O1 -28.3(3) . . . . ? C28 O2 C27 C25 61.8(3) . . . . ? C28 O2 C27 C6 -171.7(2) . . . . ? C26 C25 C27 O2 -123.0(2) . . . . ? C24 C25 C27 O2 52.0(3) . . . . ? C26 C25 C27 C6 114.4(2) . . . . ? C24 C25 C27 C6 -70.6(3) . . . . ? C1 C6 C27 O2 -154.2(2) . . . . ? C5 C6 C27 O2 27.4(3) . . . . ? C1 C6 C27 C25 -29.0(3) . . . . ? C5 C6 C27 C25 152.6(2) . . . . ? C24 C19 C29 C12 174.0(2) . . . . ? C20 C19 C29 C12 -0.4(4) . . . . ? C11 C12 C29 C19 41.3(4) . . . . ? C7 C12 C29 C19 -139.3(3) . . . . ? C31 O4 C30 O3 4.3(4) . . . . ? C31 O4 C30 C21 -176.1(2) . . . . ? C32 C21 C30 O3 91.8(3) . . . . ? C22 C21 C30 O3 -26.1(4) . . . . ? C20 C21 C30 O3 -145.8(3) . . . . ? C32 C21 C30 O4 -87.8(3) . . . . ? C22 C21 C30 O4 154.3(2) . . . . ? C20 C21 C30 O4 34.6(3) . . . . ? C33 O6 C32 O5 0.8(5) . . . . ? C33 O6 C32 C21 -176.8(2) . . . . ? C30 C21 C32 O5 -94.8(4) . . . . ? C22 C21 C32 O5 22.5(4) . . . . ? C20 C21 C32 O5 143.4(3) . . . . ? C30 C21 C32 O6 82.8(3) . . . . ? C22 C21 C32 O6 -159.9(2) . . . . ? C20 C21 C32 O6 -39.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.295 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.034