# 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 'Zhang, Junliang' _publ_contact_author_email jlzhang@chem.ecnu.edu.cn _publ_section_title ; Rhodium-Catalyzed Domino Heterocyclization and [(3+2)+2] Cycloaddition: Construction of Fused Tricycloheptadienes. ; loop_ _publ_author_name 'Junliang Zhang' 'Wanxiang Zhao' # Attachment '- 3bf.cif' data_3bf _database_code_depnum_ccdc_archive 'CCDC 744681' #TrackingRef '- 3bf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H25 N O7' _chemical_formula_weight 499.50 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 7.9544(2) _cell_length_b 11.8108(3) _cell_length_c 14.0463(4) _cell_angle_alpha 92.2960(10) _cell_angle_beta 106.1490(10) _cell_angle_gamma 107.5580(10) _cell_volume 1197.37(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.474 _exptl_crystal_size_mid 0.347 _exptl_crystal_size_min 0.243 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895823 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 13978 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4202 _reflns_number_gt 3809 _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^)+(0.0507P)^2^+0.6374P] 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 4202 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.72488(18) 0.66115(13) 1.11203(10) 0.0326(3) Uani 1 1 d . . . C1 C 0.7341(2) 0.39984(14) 0.96001(11) 0.0265(3) Uani 1 1 d . . . H1A H 0.7327 0.3198 0.9665 0.032 Uiso 1 1 calc R . . C2 C 0.7344(2) 0.47086(14) 1.04062(11) 0.0281(3) Uani 1 1 d . . . H2A H 0.7354 0.4410 1.1025 0.034 Uiso 1 1 calc R . . C3 C 0.7332(2) 0.58643(14) 1.02920(11) 0.0267(3) Uani 1 1 d . . . C4 C 0.7321(2) 0.63233(14) 0.94024(12) 0.0307(4) Uani 1 1 d . . . H4A H 0.7296 0.7116 0.9337 0.037 Uiso 1 1 calc R . . C5 C 0.7345(2) 0.56055(14) 0.86113(12) 0.0286(3) Uani 1 1 d . . . H5A H 0.7352 0.5915 0.7998 0.034 Uiso 1 1 calc R . . C6 C 0.73595(19) 0.44321(13) 0.86912(11) 0.0234(3) Uani 1 1 d . . . C7 C 0.7333(2) 0.36872(13) 0.78042(11) 0.0227(3) Uani 1 1 d . . . C8 C 0.8541(2) 0.41925(13) 0.73144(11) 0.0253(3) Uani 1 1 d . . . H8A H 0.9370 0.4962 0.7633 0.030 Uiso 1 1 calc R . . C9 C 0.8841(2) 0.38072(13) 0.64006(11) 0.0251(3) Uani 1 1 d . . . H9A H 0.9978 0.4253 0.6301 0.030 Uiso 1 1 calc R . . C10 C 0.7721(2) 0.29004(13) 0.56746(11) 0.0229(3) Uani 1 1 d . . . C11 C 0.5945(2) 0.21123(12) 0.56897(10) 0.0216(3) Uani 1 1 d . . . C12 C 0.50453(19) 0.19766(12) 0.64559(10) 0.0207(3) Uani 1 1 d . . . C13 C 0.59257(19) 0.24246(12) 0.75621(10) 0.0214(3) Uani 1 1 d . . . H13A H 0.4903 0.2456 0.7834 0.026 Uiso 1 1 calc R . . C14 C 0.6725(2) 0.15060(13) 0.80833(10) 0.0237(3) Uani 1 1 d . . . C15 C 0.8357(2) 0.13824(14) 0.79921(12) 0.0293(3) Uani 1 1 d . . . H15A H 0.9021 0.1895 0.7621 0.035 Uiso 1 1 calc R . . C16 C 0.9021(2) 0.05162(15) 0.84399(14) 0.0382(4) Uani 1 1 d . . . H16A H 1.0139 0.0439 0.8373 0.046 Uiso 1 1 calc R . . C17 C 0.8077(3) -0.02364(15) 0.89820(14) 0.0407(4) Uani 1 1 d . . . H17A H 0.8542 -0.0829 0.9288 0.049 Uiso 1 1 calc R . . C18 C 0.6454(3) -0.01216(16) 0.90765(13) 0.0398(4) Uani 1 1 d . . . H18A H 0.5795 -0.0637 0.9448 0.048 Uiso 1 1 calc R . . C19 C 0.5784(2) 0.07455(15) 0.86301(12) 0.0328(4) Uani 1 1 d . . . H19A H 0.4667 0.0820 0.8699 0.039 Uiso 1 1 calc R . . C20 C 0.4666(2) 0.14461(13) 0.48405(11) 0.0237(3) Uani 1 1 d . . . C21 C 0.3284(2) 0.12565(13) 0.60121(11) 0.0234(3) Uani 1 1 d . . . C22 C 0.1639(2) 0.08011(15) 0.63629(12) 0.0304(4) Uani 1 1 d . . . H22A H 0.1970 0.1095 0.7075 0.046 Uiso 1 1 calc R . . H22B H 0.1212 -0.0077 0.6265 0.046 Uiso 1 1 calc R . . H22C H 0.0649 0.1085 0.5980 0.046 Uiso 1 1 calc R . . C23 C 0.4862(2) 0.13623(14) 0.38190(11) 0.0271(3) Uani 1 1 d . . . H23A H 0.3683 0.1301 0.3308 0.033 Uiso 1 1 calc R . . H23B H 0.5209 0.0648 0.3684 0.033 Uiso 1 1 calc R . . C24 C 0.6406(2) 0.25230(13) 0.37943(11) 0.0243(3) Uani 1 1 d . . . C25 C 0.8141(2) 0.27145(14) 0.47090(11) 0.0249(3) Uani 1 1 d . . . H25A H 0.8560 0.2007 0.4702 0.030 Uiso 1 1 calc R . . H25B H 0.9155 0.3423 0.4664 0.030 Uiso 1 1 calc R . . C26 C 0.5647(2) 0.35742(13) 0.38074(10) 0.0245(3) Uani 1 1 d . . . C27 C 0.6467(3) 0.56852(15) 0.40495(14) 0.0357(4) Uani 1 1 d . . . H27A H 0.7575 0.6397 0.4227 0.054 Uiso 1 1 calc R . . H27B H 0.5807 0.5676 0.4545 0.054 Uiso 1 1 calc R . . H27C H 0.5655 0.5705 0.3387 0.054 Uiso 1 1 calc R . . C28 C 0.6881(2) 0.24784(13) 0.28168(12) 0.0279(3) Uani 1 1 d . . . C29 C 0.8771(3) 0.19124(19) 0.19936(15) 0.0478(5) Uani 1 1 d . . . H29A H 0.9683 0.1490 0.2106 0.072 Uiso 1 1 calc R . . H29B H 0.9345 0.2735 0.1882 0.072 Uiso 1 1 calc R . . H29C H 0.7719 0.1496 0.1405 0.072 Uiso 1 1 calc R . . O1 O 0.6203(2) 0.28775(13) 0.20961(9) 0.0504(4) Uani 1 1 d . . . O2 O 0.81341(19) 0.19373(12) 0.28591(9) 0.0415(3) Uani 1 1 d . . . O3 O 0.40361(16) 0.34637(11) 0.36296(9) 0.0363(3) Uani 1 1 d . . . O4 O 0.70035(15) 0.46171(9) 0.40342(9) 0.0314(3) Uani 1 1 d . . . O5 O 0.73736(19) 0.62371(13) 1.19275(9) 0.0461(3) Uani 1 1 d . . . O6 O 0.70456(17) 0.75910(11) 1.09682(10) 0.0422(3) Uani 1 1 d . . . O7 O 0.30201(14) 0.09125(9) 0.50089(7) 0.0256(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0231(7) 0.0392(8) 0.0307(8) -0.0082(6) 0.0074(5) 0.0054(6) C1 0.0287(8) 0.0252(8) 0.0240(8) 0.0038(6) 0.0048(6) 0.0097(6) C2 0.0264(8) 0.0346(8) 0.0199(7) 0.0030(6) 0.0042(6) 0.0080(6) C3 0.0205(7) 0.0302(8) 0.0255(8) -0.0052(6) 0.0058(6) 0.0050(6) C4 0.0345(9) 0.0230(8) 0.0332(9) 0.0016(6) 0.0096(7) 0.0084(7) C5 0.0347(8) 0.0271(8) 0.0239(8) 0.0054(6) 0.0092(6) 0.0094(7) C6 0.0206(7) 0.0250(7) 0.0217(7) 0.0016(6) 0.0038(6) 0.0062(6) C7 0.0233(7) 0.0224(7) 0.0210(7) 0.0029(6) 0.0027(6) 0.0093(6) C8 0.0247(7) 0.0228(7) 0.0249(8) 0.0014(6) 0.0044(6) 0.0057(6) C9 0.0224(7) 0.0276(8) 0.0264(8) 0.0064(6) 0.0092(6) 0.0078(6) C10 0.0246(7) 0.0250(7) 0.0224(7) 0.0066(6) 0.0073(6) 0.0123(6) C11 0.0263(7) 0.0203(7) 0.0201(7) 0.0050(6) 0.0068(6) 0.0102(6) C12 0.0243(7) 0.0181(7) 0.0213(7) 0.0043(5) 0.0067(6) 0.0094(6) C13 0.0230(7) 0.0217(7) 0.0201(7) 0.0023(6) 0.0072(6) 0.0078(6) C14 0.0276(8) 0.0211(7) 0.0179(7) 0.0000(6) 0.0029(6) 0.0057(6) C15 0.0271(8) 0.0242(8) 0.0335(9) 0.0056(6) 0.0061(6) 0.0067(6) C16 0.0305(9) 0.0296(9) 0.0497(11) 0.0065(8) 0.0022(8) 0.0121(7) C17 0.0443(10) 0.0261(8) 0.0400(10) 0.0103(7) -0.0045(8) 0.0103(7) C18 0.0519(11) 0.0319(9) 0.0309(9) 0.0144(7) 0.0103(8) 0.0078(8) C19 0.0390(9) 0.0316(9) 0.0285(8) 0.0076(7) 0.0130(7) 0.0095(7) C20 0.0261(7) 0.0211(7) 0.0243(8) 0.0049(6) 0.0076(6) 0.0079(6) C21 0.0274(8) 0.0217(7) 0.0214(7) 0.0040(6) 0.0069(6) 0.0090(6) C22 0.0257(8) 0.0322(8) 0.0300(8) 0.0036(7) 0.0086(6) 0.0050(6) C23 0.0331(8) 0.0245(8) 0.0217(7) 0.0017(6) 0.0067(6) 0.0081(6) C24 0.0302(8) 0.0243(8) 0.0207(7) 0.0037(6) 0.0086(6) 0.0111(6) C25 0.0267(8) 0.0275(8) 0.0241(8) 0.0054(6) 0.0090(6) 0.0128(6) C26 0.0307(8) 0.0287(8) 0.0172(7) 0.0068(6) 0.0090(6) 0.0124(6) C27 0.0467(10) 0.0263(8) 0.0411(10) 0.0066(7) 0.0156(8) 0.0197(7) C28 0.0366(8) 0.0231(7) 0.0256(8) 0.0035(6) 0.0123(7) 0.0096(7) C29 0.0631(13) 0.0519(12) 0.0450(11) 0.0059(9) 0.0359(10) 0.0244(10) O1 0.0804(10) 0.0654(9) 0.0296(7) 0.0222(6) 0.0267(7) 0.0471(8) O2 0.0566(8) 0.0542(8) 0.0328(7) 0.0116(6) 0.0246(6) 0.0346(7) O3 0.0308(6) 0.0384(7) 0.0458(7) 0.0132(5) 0.0139(5) 0.0169(5) O4 0.0332(6) 0.0234(6) 0.0393(7) 0.0053(5) 0.0092(5) 0.0133(5) O5 0.0487(8) 0.0647(9) 0.0271(7) -0.0030(6) 0.0133(6) 0.0213(7) O6 0.0421(7) 0.0340(7) 0.0505(8) -0.0095(6) 0.0186(6) 0.0104(5) O7 0.0262(5) 0.0245(5) 0.0213(5) 0.0019(4) 0.0049(4) 0.0037(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O5 1.2228(19) . ? N1 O6 1.2343(19) . ? N1 C3 1.460(2) . ? C1 C2 1.381(2) . ? C1 C6 1.397(2) . ? C1 H1A 0.9500 . ? C2 C3 1.383(2) . ? C2 H2A 0.9500 . ? C3 C4 1.381(2) . ? C4 C5 1.378(2) . ? C4 H4A 0.9500 . ? C5 C6 1.398(2) . ? C5 H5A 0.9500 . ? C6 C7 1.488(2) . ? C7 C8 1.344(2) . ? C7 C13 1.527(2) . ? C8 C9 1.449(2) . ? C8 H8A 0.9500 . ? C9 C10 1.346(2) . ? C9 H9A 0.9500 . ? C10 C11 1.445(2) . ? C10 C25 1.507(2) . ? C11 C20 1.358(2) . ? C11 C12 1.438(2) . ? C12 C21 1.352(2) . ? C12 C13 1.513(2) . ? C13 C14 1.529(2) . ? C13 H13A 1.0000 . ? C14 C19 1.388(2) . ? C14 C15 1.389(2) . ? C15 C16 1.383(2) . ? C15 H15A 0.9500 . ? C16 C17 1.379(3) . ? C16 H16A 0.9500 . ? C17 C18 1.380(3) . ? C17 H17A 0.9500 . ? C18 C19 1.386(2) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 O7 1.3615(18) . ? C20 C23 1.488(2) . ? C21 O7 1.3903(18) . ? C21 C22 1.483(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.549(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C28 1.525(2) . ? C24 C26 1.537(2) . ? C24 C25 1.552(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O3 1.1995(19) . ? C26 O4 1.3262(19) . ? C27 O4 1.4500(19) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O1 1.194(2) . ? C28 O2 1.327(2) . ? C29 O2 1.444(2) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 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 O5 N1 O6 123.16(14) . . ? O5 N1 C3 118.66(15) . . ? O6 N1 C3 118.18(14) . . ? C2 C1 C6 121.37(14) . . ? C2 C1 H1A 119.3 . . ? C6 C1 H1A 119.3 . . ? C1 C2 C3 118.50(14) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C4 C3 C2 122.07(14) . . ? C4 C3 N1 118.52(14) . . ? C2 C3 N1 119.36(14) . . ? C5 C4 C3 118.52(15) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C4 C5 C6 121.49(14) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C1 C6 C5 118.05(14) . . ? C1 C6 C7 122.78(13) . . ? C5 C6 C7 119.14(13) . . ? C8 C7 C6 116.91(13) . . ? C8 C7 C13 127.65(14) . . ? C6 C7 C13 115.43(12) . . ? C7 C8 C9 133.31(14) . . ? C7 C8 H8A 113.3 . . ? C9 C8 H8A 113.3 . . ? C10 C9 C8 128.47(14) . . ? C10 C9 H9A 115.8 . . ? C8 C9 H9A 115.8 . . ? C9 C10 C11 124.28(14) . . ? C9 C10 C25 121.51(14) . . ? C11 C10 C25 113.87(13) . . ? C20 C11 C12 106.51(13) . . ? C20 C11 C10 121.22(13) . . ? C12 C11 C10 131.65(13) . . ? C21 C12 C11 106.27(13) . . ? C21 C12 C13 126.03(13) . . ? C11 C12 C13 127.37(13) . . ? C12 C13 C7 114.48(12) . . ? C12 C13 C14 109.46(11) . . ? C7 C13 C14 112.50(12) . . ? C12 C13 H13A 106.6 . . ? C7 C13 H13A 106.6 . . ? C14 C13 H13A 106.6 . . ? C19 C14 C15 118.64(14) . . ? C19 C14 C13 120.14(14) . . ? C15 C14 C13 121.19(13) . . ? C16 C15 C14 120.25(15) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 120.74(17) . . ? C17 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C16 C17 C18 119.46(16) . . ? C16 C17 H17A 120.3 . . ? C18 C17 H17A 120.3 . . ? C17 C18 C19 120.01(16) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C14 120.89(16) . . ? C18 C19 H19A 119.6 . . ? C14 C19 H19A 119.6 . . ? C11 C20 O7 110.64(13) . . ? C11 C20 C23 127.60(14) . . ? O7 C20 C23 121.49(13) . . ? C12 C21 O7 110.18(12) . . ? C12 C21 C22 133.85(14) . . ? O7 C21 C22 115.95(12) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 C24 106.32(12) . . ? C20 C23 H23A 110.5 . . ? C24 C23 H23A 110.5 . . ? C20 C23 H23B 110.5 . . ? C24 C23 H23B 110.5 . . ? H23A C23 H23B 108.7 . . ? C28 C24 C26 105.70(11) . . ? C28 C24 C23 111.11(12) . . ? C26 C24 C23 108.06(12) . . ? C28 C24 C25 111.08(12) . . ? C26 C24 C25 111.12(12) . . ? C23 C24 C25 109.68(12) . . ? C10 C25 C24 110.99(12) . . ? C10 C25 H25A 109.4 . . ? C24 C25 H25A 109.4 . . ? C10 C25 H25B 109.4 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? O3 C26 O4 124.55(14) . . ? O3 C26 C24 124.33(14) . . ? O4 C26 C24 111.12(12) . . ? O4 C27 H27A 109.5 . . ? O4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O1 C28 O2 123.82(15) . . ? O1 C28 C24 124.21(15) . . ? O2 C28 C24 111.97(13) . . ? O2 C29 H29A 109.5 . . ? O2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 O2 C29 116.54(14) . . ? C26 O4 C27 116.63(12) . . ? C20 O7 C21 106.39(11) . . ? 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 1.1(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C1 C2 C3 N1 177.21(13) . . . . ? O5 N1 C3 C4 -175.56(14) . . . . ? O6 N1 C3 C4 4.8(2) . . . . ? O5 N1 C3 C2 7.0(2) . . . . ? O6 N1 C3 C2 -172.60(14) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? N1 C3 C4 C5 -178.15(14) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C2 C1 C6 C5 -1.2(2) . . . . ? C2 C1 C6 C7 -179.21(14) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C4 C5 C6 C7 178.33(14) . . . . ? C1 C6 C7 C8 -133.87(15) . . . . ? C5 C6 C7 C8 48.2(2) . . . . ? C1 C6 C7 C13 45.87(19) . . . . ? C5 C6 C7 C13 -132.11(14) . . . . ? C6 C7 C8 C9 -174.60(15) . . . . ? C13 C7 C8 C9 5.7(3) . . . . ? C7 C8 C9 C10 14.4(3) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C8 C9 C10 C25 172.34(14) . . . . ? C9 C10 C11 C20 161.42(15) . . . . ? C25 C10 C11 C20 -12.0(2) . . . . ? C9 C10 C11 C12 -8.3(2) . . . . ? C25 C10 C11 C12 178.36(14) . . . . ? C20 C11 C12 C21 -1.00(16) . . . . ? C10 C11 C12 C21 169.80(15) . . . . ? C20 C11 C12 C13 172.65(13) . . . . ? C10 C11 C12 C13 -16.5(2) . . . . ? C21 C12 C13 C7 -145.50(14) . . . . ? C11 C12 C13 C7 42.04(19) . . . . ? C21 C12 C13 C14 87.14(17) . . . . ? C11 C12 C13 C14 -85.32(17) . . . . ? C8 C7 C13 C12 -36.5(2) . . . . ? C6 C7 C13 C12 143.81(13) . . . . ? C8 C7 C13 C14 89.30(18) . . . . ? C6 C7 C13 C14 -90.40(15) . . . . ? C12 C13 C14 C19 -102.32(16) . . . . ? C7 C13 C14 C19 129.21(15) . . . . ? C12 C13 C14 C15 75.29(17) . . . . ? C7 C13 C14 C15 -53.17(18) . . . . ? C19 C14 C15 C16 0.0(2) . . . . ? C13 C14 C15 C16 -177.64(14) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C17 C18 C19 C14 0.1(3) . . . . ? C15 C14 C19 C18 -0.1(2) . . . . ? C13 C14 C19 C18 177.61(14) . . . . ? C12 C11 C20 O7 0.80(16) . . . . ? C10 C11 C20 O7 -171.17(12) . . . . ? C12 C11 C20 C23 174.82(14) . . . . ? C10 C11 C20 C23 2.9(2) . . . . ? C11 C12 C21 O7 0.85(16) . . . . ? C13 C12 C21 O7 -172.91(12) . . . . ? C11 C12 C21 C22 -177.71(16) . . . . ? C13 C12 C21 C22 8.5(3) . . . . ? C11 C20 C23 C24 -22.9(2) . . . . ? O7 C20 C23 C24 150.51(13) . . . . ? C20 C23 C24 C28 173.76(12) . . . . ? C20 C23 C24 C26 -70.71(14) . . . . ? C20 C23 C24 C25 50.57(16) . . . . ? C9 C10 C25 C24 -131.89(15) . . . . ? C11 C10 C25 C24 41.69(17) . . . . ? C28 C24 C25 C10 173.47(12) . . . . ? C26 C24 C25 C10 56.10(16) . . . . ? C23 C24 C25 C10 -63.32(16) . . . . ? C28 C24 C26 O3 103.17(16) . . . . ? C23 C24 C26 O3 -15.85(19) . . . . ? C25 C24 C26 O3 -136.23(15) . . . . ? C28 C24 C26 O4 -76.41(15) . . . . ? C23 C24 C26 O4 164.57(12) . . . . ? C25 C24 C26 O4 44.19(16) . . . . ? C26 C24 C28 O1 -23.4(2) . . . . ? C23 C24 C28 O1 93.63(19) . . . . ? C25 C24 C28 O1 -143.99(17) . . . . ? C26 C24 C28 O2 156.94(13) . . . . ? C23 C24 C28 O2 -86.08(16) . . . . ? C25 C24 C28 O2 36.30(17) . . . . ? O1 C28 O2 C29 4.1(3) . . . . ? C24 C28 O2 C29 -176.23(15) . . . . ? O3 C26 O4 C27 -0.9(2) . . . . ? C24 C26 O4 C27 178.65(12) . . . . ? C11 C20 O7 C21 -0.29(16) . . . . ? C23 C20 O7 C21 -174.74(13) . . . . ? C12 C21 O7 C20 -0.38(16) . . . . ? C22 C21 O7 C20 178.47(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.303 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.041 # Attachment '- 3ad.cif' data_3ad _database_code_depnum_ccdc_archive 'CCDC 744682' #TrackingRef '- 3ad.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H32 O7' _chemical_formula_weight 576.62 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 P2(1)/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 19.1051(14) _cell_length_b 17.2655(13) _cell_length_c 9.1572(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.382(3) _cell_angle_gamma 90.00 _cell_volume 2938.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9810 _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 33980 _diffrn_reflns_av_R_equivalents 0.1318 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5182 _reflns_number_gt 2442 _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^)+(0.0495P)^2^+1.4859P] 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 5182 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.30814(12) 0.58375(13) 0.5969(3) 0.0526(6) Uani 1 1 d . . . O2 O 0.1489(2) 0.62850(15) -0.0467(3) 0.1095(13) Uani 1 1 d . . . O3 O 0.22912(19) 0.70958(17) 0.0765(3) 0.1019(11) Uani 1 1 d . . . O4 O 0.10290(15) 0.51183(16) 0.1704(3) 0.0741(8) Uani 1 1 d . . . O5 O 0.10353(17) 0.62054(17) 0.2970(4) 0.0966(10) Uani 1 1 d . . . O6 O 0.03816(15) 0.19926(16) -0.0013(3) 0.0811(9) Uani 1 1 d . . . O7 O 0.08208(14) 0.06063(15) 0.0784(3) 0.0716(8) Uani 1 1 d . . . C1 C 0.44278(19) 0.3962(2) 0.4753(4) 0.0548(10) Uani 1 1 d . . . H1A H 0.4197 0.4402 0.4289 0.066 Uiso 1 1 calc R . . C2 C 0.5097(2) 0.3762(2) 0.4534(4) 0.0622(11) Uani 1 1 d . . . H2A H 0.5311 0.4069 0.3926 0.075 Uiso 1 1 calc R . . C3 C 0.5446(2) 0.3118(3) 0.5205(5) 0.0688(12) Uani 1 1 d . . . H3A H 0.5895 0.2983 0.5051 0.083 Uiso 1 1 calc R . . C4 C 0.5123(2) 0.2673(3) 0.6109(5) 0.0790(13) Uani 1 1 d . . . H4A H 0.5355 0.2233 0.6568 0.095 Uiso 1 1 calc R . . C5 C 0.4463(2) 0.2875(2) 0.6339(5) 0.0656(11) Uani 1 1 d . . . H5A H 0.4256 0.2575 0.6970 0.079 Uiso 1 1 calc R . . C6 C 0.41000(18) 0.35179(19) 0.5647(4) 0.0436(9) Uani 1 1 d . . . C7 C 0.3654(2) 0.5942(2) 0.8979(4) 0.0627(11) Uani 1 1 d . . . H7A H 0.3442 0.6367 0.8423 0.075 Uiso 1 1 calc R . . C8 C 0.3986(2) 0.6032(3) 1.0479(5) 0.0737(13) Uani 1 1 d . . . H8A H 0.4003 0.6520 1.0915 0.088 Uiso 1 1 calc R . . C9 C 0.4288(2) 0.5419(3) 1.1331(5) 0.0697(12) Uani 1 1 d . . . H9A H 0.4508 0.5484 1.2341 0.084 Uiso 1 1 calc R . . C10 C 0.4264(2) 0.4707(3) 1.0677(4) 0.0720(12) Uani 1 1 d . . . H10A H 0.4459 0.4283 1.1256 0.086 Uiso 1 1 calc R . . C11 C 0.3954(2) 0.4603(2) 0.9174(4) 0.0629(11) Uani 1 1 d . . . H11A H 0.3958 0.4115 0.8746 0.075 Uiso 1 1 calc R . . C12 C 0.36364(18) 0.5219(2) 0.8294(4) 0.0479(9) Uani 1 1 d . . . C13 C 0.22349(19) 0.1745(2) 0.3312(4) 0.0465(9) Uani 1 1 d . . . H13A H 0.2651 0.1669 0.4060 0.056 Uiso 1 1 calc R . . C14 C 0.1840(2) 0.1103(2) 0.2643(4) 0.0516(10) Uani 1 1 d . . . H14A H 0.1993 0.0607 0.2961 0.062 Uiso 1 1 calc R . . C15 C 0.1228(2) 0.1197(2) 0.1522(4) 0.0511(9) Uani 1 1 d . . . C16 C 0.09972(19) 0.1945(2) 0.1091(4) 0.0527(10) Uani 1 1 d . . . C17 C 0.13803(19) 0.2572(2) 0.1770(4) 0.0480(9) Uani 1 1 d . . . H17A H 0.1212 0.3067 0.1485 0.058 Uiso 1 1 calc R . . C18 C 0.20161(18) 0.24868(19) 0.2878(4) 0.0429(8) Uani 1 1 d . . . C19 C 0.24493(17) 0.31791(18) 0.3535(4) 0.0415(8) Uani 1 1 d . . . C20 C 0.24191(17) 0.38271(19) 0.2475(4) 0.0463(9) Uani 1 1 d . . . H20A H 0.2283 0.3698 0.1462 0.056 Uiso 1 1 calc R . . C21 C 0.25615(17) 0.45735(19) 0.2776(3) 0.0423(8) Uani 1 1 d . . . C22 C 0.28243(17) 0.48966(19) 0.4260(4) 0.0441(9) Uani 1 1 d . . . C23 C 0.31563(17) 0.45458(19) 0.5672(4) 0.0424(8) Uani 1 1 d . . . C24 C 0.33503(17) 0.37034(18) 0.5895(3) 0.0421(8) Uani 1 1 d . . . H24A H 0.3368 0.3587 0.6950 0.050 Uiso 1 1 calc R . . C25 C 0.28050(18) 0.31556(19) 0.4974(4) 0.0461(9) Uani 1 1 d . . . H25A H 0.2699 0.2728 0.5500 0.055 Uiso 1 1 calc R . . C26 C 0.33061(18) 0.5134(2) 0.6688(4) 0.0465(9) Uani 1 1 d . . . C27 C 0.28019(18) 0.56612(19) 0.4502(4) 0.0482(9) Uani 1 1 d . . . C28 C 0.2545(2) 0.62892(19) 0.3408(4) 0.0597(11) Uani 1 1 d . . . H28A H 0.2951 0.6550 0.3156 0.072 Uiso 1 1 calc R . . H28B H 0.2273 0.6666 0.3833 0.072 Uiso 1 1 calc R . . C29 C 0.20632(19) 0.59216(19) 0.1986(4) 0.0503(9) Uani 1 1 d . . . C30 C 0.2415(2) 0.51761(18) 0.1547(4) 0.0523(9) Uani 1 1 d . . . H30A H 0.2101 0.4954 0.0661 0.063 Uiso 1 1 calc R . . H30B H 0.2865 0.5312 0.1292 0.063 Uiso 1 1 calc R . . C31 C 0.1973(2) 0.6508(2) 0.0715(5) 0.0630(11) Uani 1 1 d . . . C32 C 0.1375(4) 0.6817(3) -0.1750(5) 0.154(3) Uani 1 1 d . . . H32A H 0.1013 0.6610 -0.2562 0.232 Uiso 1 1 calc R . . H32B H 0.1816 0.6879 -0.2067 0.232 Uiso 1 1 calc R . . H32C H 0.1220 0.7311 -0.1460 0.232 Uiso 1 1 calc R . . C33 C 0.1318(2) 0.5770(2) 0.2272(4) 0.0573(10) Uani 1 1 d . . . C34 C 0.0340(2) 0.4912(3) 0.2025(5) 0.0933(15) Uani 1 1 d . . . H34A H 0.0179 0.4426 0.1557 0.140 Uiso 1 1 calc R . . H34B H -0.0008 0.5307 0.1640 0.140 Uiso 1 1 calc R . . H34C H 0.0394 0.4868 0.3091 0.140 Uiso 1 1 calc R . . C35 C 0.0159(3) 0.2747(3) -0.0545(6) 0.1107(19) Uani 1 1 d . . . H35A H -0.0277 0.2712 -0.1312 0.166 Uiso 1 1 calc R . . H35B H 0.0528 0.2983 -0.0951 0.166 Uiso 1 1 calc R . . H35C H 0.0077 0.3056 0.0271 0.166 Uiso 1 1 calc R . . C36 C 0.1069(2) -0.0156(2) 0.1172(5) 0.0821(14) Uani 1 1 d . . . H36A H 0.0742 -0.0521 0.0586 0.123 Uiso 1 1 calc R . . H36B H 0.1096 -0.0243 0.2219 0.123 Uiso 1 1 calc R . . H36C H 0.1537 -0.0221 0.0974 0.123 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 0.0558(16) 0.0459(15) 0.0505(15) -0.0106(12) 0.0009(13) -0.0010(12) O2 0.164(3) 0.0571(19) 0.074(2) 0.0254(16) -0.041(2) -0.029(2) O3 0.135(3) 0.068(2) 0.086(2) 0.0220(18) -0.008(2) -0.036(2) O4 0.0624(19) 0.0728(19) 0.086(2) -0.0107(16) 0.0145(16) -0.0140(16) O5 0.093(2) 0.070(2) 0.134(3) -0.014(2) 0.041(2) 0.0110(18) O6 0.0663(19) 0.070(2) 0.089(2) -0.0026(16) -0.0207(17) -0.0051(16) O7 0.080(2) 0.0536(17) 0.0742(19) -0.0096(15) 0.0041(15) -0.0205(15) C1 0.051(3) 0.062(2) 0.051(2) 0.0080(19) 0.012(2) 0.0071(19) C2 0.054(3) 0.077(3) 0.057(2) -0.001(2) 0.016(2) -0.002(2) C3 0.046(3) 0.081(3) 0.077(3) -0.019(3) 0.011(2) 0.007(2) C4 0.068(3) 0.071(3) 0.095(4) 0.003(3) 0.014(3) 0.025(2) C5 0.065(3) 0.056(2) 0.077(3) 0.016(2) 0.018(2) 0.011(2) C6 0.044(2) 0.048(2) 0.0358(19) -0.0052(17) 0.0031(17) -0.0003(18) C7 0.078(3) 0.060(3) 0.050(2) -0.007(2) 0.014(2) -0.023(2) C8 0.102(4) 0.066(3) 0.053(3) -0.015(2) 0.016(2) -0.031(3) C9 0.074(3) 0.087(3) 0.047(2) -0.013(3) 0.011(2) -0.031(3) C10 0.069(3) 0.088(3) 0.051(3) 0.001(2) -0.003(2) -0.003(2) C11 0.063(3) 0.070(3) 0.047(2) -0.006(2) -0.004(2) 0.003(2) C12 0.044(2) 0.055(2) 0.043(2) -0.0079(19) 0.0070(18) -0.0106(18) C13 0.048(2) 0.052(2) 0.040(2) 0.0001(18) 0.0109(17) -0.0007(18) C14 0.070(3) 0.040(2) 0.048(2) 0.0031(18) 0.018(2) 0.0015(19) C15 0.054(2) 0.051(2) 0.048(2) -0.0053(19) 0.012(2) -0.013(2) C16 0.046(2) 0.057(3) 0.051(2) -0.003(2) 0.003(2) -0.003(2) C17 0.050(2) 0.043(2) 0.049(2) -0.0020(17) 0.0091(19) 0.0011(18) C18 0.047(2) 0.041(2) 0.041(2) 0.0009(17) 0.0121(18) -0.0009(18) C19 0.043(2) 0.041(2) 0.041(2) 0.0010(17) 0.0110(17) 0.0007(16) C20 0.053(2) 0.047(2) 0.0379(19) -0.0023(17) 0.0079(17) -0.0003(18) C21 0.043(2) 0.045(2) 0.038(2) -0.0005(17) 0.0076(17) 0.0005(17) C22 0.041(2) 0.042(2) 0.045(2) -0.0016(17) 0.0020(17) 0.0019(17) C23 0.037(2) 0.048(2) 0.042(2) -0.0019(17) 0.0071(17) -0.0022(17) C24 0.048(2) 0.044(2) 0.0333(19) 0.0036(16) 0.0082(16) -0.0027(17) C25 0.049(2) 0.047(2) 0.044(2) 0.0053(17) 0.0120(18) -0.0024(17) C26 0.044(2) 0.045(2) 0.048(2) -0.0014(19) 0.0050(18) 0.0017(17) C27 0.048(2) 0.043(2) 0.048(2) -0.0026(18) 0.0004(18) 0.0015(18) C28 0.064(3) 0.043(2) 0.064(3) -0.003(2) -0.001(2) 0.0024(19) C29 0.055(2) 0.037(2) 0.052(2) 0.0059(17) -0.0024(19) 0.0020(18) C30 0.060(2) 0.047(2) 0.048(2) 0.0039(18) 0.0078(19) -0.0057(19) C31 0.079(3) 0.042(2) 0.061(3) 0.003(2) 0.001(2) -0.007(2) C32 0.269(8) 0.066(3) 0.082(4) 0.041(3) -0.056(4) -0.032(4) C33 0.061(3) 0.046(2) 0.059(3) 0.007(2) 0.004(2) 0.010(2) C34 0.065(3) 0.122(4) 0.092(3) 0.001(3) 0.015(3) -0.028(3) C35 0.090(4) 0.090(4) 0.120(4) -0.002(3) -0.042(3) 0.019(3) C36 0.107(4) 0.052(3) 0.087(3) -0.008(2) 0.022(3) -0.012(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 C27 1.360(4) . ? O1 C26 1.401(4) . ? O2 C31 1.308(4) . ? O2 C32 1.468(5) . ? O3 C31 1.178(4) . ? O4 C33 1.307(4) . ? O4 C34 1.458(4) . ? O5 C33 1.194(4) . ? O6 C16 1.364(4) . ? O6 C35 1.421(5) . ? O7 C15 1.364(4) . ? O7 C36 1.416(4) . ? C1 C6 1.374(4) . ? C1 C2 1.383(5) . ? C1 H1A 0.9300 . ? C2 C3 1.368(5) . ? C2 H2A 0.9300 . ? C3 C4 1.376(5) . ? C3 H3A 0.9300 . ? C4 C5 1.372(5) . ? C4 H4A 0.9300 . ? C5 C6 1.382(5) . ? C5 H5A 0.9300 . ? C6 C24 1.535(4) . ? C7 C8 1.382(5) . ? C7 C12 1.394(5) . ? C7 H7A 0.9300 . ? C8 C9 1.362(5) . ? C8 H8A 0.9300 . ? C9 C10 1.364(5) . ? C9 H9A 0.9300 . ? C10 C11 1.378(5) . ? C10 H10A 0.9300 . ? C11 C12 1.386(5) . ? C11 H11A 0.9300 . ? C12 C26 1.468(4) . ? C13 C18 1.378(4) . ? C13 C14 1.398(4) . ? C13 H13A 0.9300 . ? C14 C15 1.375(5) . ? C14 H14A 0.9300 . ? C15 C16 1.392(5) . ? C16 C17 1.372(4) . ? C17 C18 1.399(4) . ? C17 H17A 0.9300 . ? C18 C19 1.498(4) . ? C19 C25 1.336(4) . ? C19 C20 1.474(4) . ? C20 C21 1.333(4) . ? C20 H20A 0.9300 . ? C21 C22 1.447(4) . ? C21 C30 1.510(4) . ? C22 C27 1.341(4) . ? C22 C23 1.436(4) . ? C23 C26 1.362(4) . ? C23 C24 1.503(4) . ? C24 C25 1.511(4) . ? C24 H24A 0.9800 . ? C25 H25A 0.9300 . ? C27 C28 1.481(4) . ? C28 C29 1.546(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C31 1.522(5) . ? C29 C33 1.528(5) . ? C29 C30 1.547(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 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 C27 O1 C26 106.1(2) . . ? C31 O2 C32 115.0(3) . . ? C33 O4 C34 116.6(3) . . ? C16 O6 C35 116.6(3) . . ? C15 O7 C36 116.8(3) . . ? C6 C1 C2 120.7(3) . . ? C6 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? C3 C2 C1 120.7(4) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C5 C4 C3 120.5(4) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 118.2(3) . . ? C1 C6 C24 122.8(3) . . ? C5 C6 C24 119.0(3) . . ? C8 C7 C12 120.3(4) . . ? C8 C7 H7A 119.8 . . ? C12 C7 H7A 119.8 . . ? C9 C8 C7 121.2(4) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C10 118.8(4) . . ? C8 C9 H9A 120.6 . . ? C10 C9 H9A 120.6 . . ? C9 C10 C11 121.3(4) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C7 117.7(3) . . ? C11 C12 C26 122.3(3) . . ? C7 C12 C26 120.0(3) . . ? C18 C13 C14 120.9(3) . . ? C18 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H14A 119.6 . . ? C13 C14 H14A 119.6 . . ? O7 C15 C14 124.8(3) . . ? O7 C15 C16 116.5(3) . . ? C14 C15 C16 118.7(3) . . ? O6 C16 C17 124.5(3) . . ? O6 C16 C15 115.4(3) . . ? C17 C16 C15 120.1(3) . . ? C16 C17 C18 121.9(3) . . ? C16 C17 H17A 119.0 . . ? C18 C17 H17A 119.0 . . ? C13 C18 C17 117.5(3) . . ? C13 C18 C19 121.6(3) . . ? C17 C18 C19 120.9(3) . . ? C25 C19 C20 127.3(3) . . ? C25 C19 C18 118.6(3) . . ? C20 C19 C18 114.0(3) . . ? C21 C20 C19 128.5(3) . . ? C21 C20 H20A 115.8 . . ? C19 C20 H20A 115.8 . . ? C20 C21 C22 125.3(3) . . ? C20 C21 C30 121.2(3) . . ? C22 C21 C30 113.5(3) . . ? C27 C22 C23 106.9(3) . . ? C27 C22 C21 121.2(3) . . ? C23 C22 C21 131.9(3) . . ? C26 C23 C22 106.2(3) . . ? C26 C23 C24 128.5(3) . . ? C22 C23 C24 125.0(3) . . ? C23 C24 C25 114.4(3) . . ? C23 C24 C6 113.0(3) . . ? C25 C24 C6 109.5(3) . . ? C23 C24 H24A 106.5 . . ? C25 C24 H24A 106.5 . . ? C6 C24 H24A 106.5 . . ? C19 C25 C24 131.2(3) . . ? C19 C25 H25A 114.4 . . ? C24 C25 H25A 114.4 . . ? C23 C26 O1 109.4(3) . . ? C23 C26 C12 137.1(3) . . ? O1 C26 C12 113.5(3) . . ? C22 C27 O1 111.3(3) . . ? C22 C27 C28 128.8(3) . . ? O1 C27 C28 119.8(3) . . ? C27 C28 C29 108.0(3) . . ? C27 C28 H28A 110.1 . . ? C29 C28 H28A 110.1 . . ? C27 C28 H28B 110.1 . . ? C29 C28 H28B 110.1 . . ? H28A C28 H28B 108.4 . . ? C31 C29 C33 107.5(3) . . ? C31 C29 C28 108.1(3) . . ? C33 C29 C28 108.8(3) . . ? C31 C29 C30 109.5(3) . . ? C33 C29 C30 112.3(3) . . ? C28 C29 C30 110.5(3) . . ? C21 C30 C29 113.4(3) . . ? C21 C30 H30A 108.9 . . ? C29 C30 H30A 108.9 . . ? C21 C30 H30B 108.9 . . ? C29 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? O3 C31 O2 123.1(4) . . ? O3 C31 C29 125.2(4) . . ? O2 C31 C29 111.7(3) . . ? O2 C32 H32A 109.5 . . ? O2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O5 C33 O4 123.6(4) . . ? O5 C33 C29 122.6(4) . . ? O4 C33 C29 113.8(4) . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O6 C35 H35A 109.5 . . ? O6 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O6 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O7 C36 H36A 109.5 . . ? O7 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O7 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 0.0(6) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 1.3(6) . . . . ? C2 C1 C6 C5 1.1(5) . . . . ? C2 C1 C6 C24 -178.5(3) . . . . ? C4 C5 C6 C1 -1.7(6) . . . . ? C4 C5 C6 C24 177.8(3) . . . . ? C12 C7 C8 C9 -1.4(6) . . . . ? C7 C8 C9 C10 0.4(6) . . . . ? C8 C9 C10 C11 1.4(6) . . . . ? C9 C10 C11 C12 -2.2(6) . . . . ? C10 C11 C12 C7 1.1(5) . . . . ? C10 C11 C12 C26 179.5(3) . . . . ? C8 C7 C12 C11 0.6(5) . . . . ? C8 C7 C12 C26 -177.8(4) . . . . ? C18 C13 C14 C15 0.8(5) . . . . ? C36 O7 C15 C14 -2.6(5) . . . . ? C36 O7 C15 C16 177.4(3) . . . . ? C13 C14 C15 O7 178.4(3) . . . . ? C13 C14 C15 C16 -1.7(5) . . . . ? C35 O6 C16 C17 4.3(5) . . . . ? C35 O6 C16 C15 -176.0(4) . . . . ? O7 C15 C16 O6 0.8(5) . . . . ? C14 C15 C16 O6 -179.1(3) . . . . ? O7 C15 C16 C17 -179.5(3) . . . . ? C14 C15 C16 C17 0.6(5) . . . . ? O6 C16 C17 C18 -178.8(3) . . . . ? C15 C16 C17 C18 1.5(5) . . . . ? C14 C13 C18 C17 1.2(5) . . . . ? C14 C13 C18 C19 -177.3(3) . . . . ? C16 C17 C18 C13 -2.3(5) . . . . ? C16 C17 C18 C19 176.2(3) . . . . ? C13 C18 C19 C25 -34.7(5) . . . . ? C17 C18 C19 C25 146.9(3) . . . . ? C13 C18 C19 C20 146.1(3) . . . . ? C17 C18 C19 C20 -32.3(4) . . . . ? C25 C19 C20 C21 -19.9(6) . . . . ? C18 C19 C20 C21 159.2(3) . . . . ? C19 C20 C21 C22 4.0(6) . . . . ? C19 C20 C21 C30 -172.4(3) . . . . ? C20 C21 C22 C27 -164.9(3) . . . . ? C30 C21 C22 C27 11.7(5) . . . . ? C20 C21 C22 C23 17.2(6) . . . . ? C30 C21 C22 C23 -166.1(3) . . . . ? C27 C22 C23 C26 0.7(4) . . . . ? C21 C22 C23 C26 178.7(3) . . . . ? C27 C22 C23 C24 -174.3(3) . . . . ? C21 C22 C23 C24 3.8(6) . . . . ? C26 C23 C24 C25 147.2(3) . . . . ? C22 C23 C24 C25 -39.0(4) . . . . ? C26 C23 C24 C6 -86.6(4) . . . . ? C22 C23 C24 C6 87.2(4) . . . . ? C1 C6 C24 C23 -25.2(4) . . . . ? C5 C6 C24 C23 155.3(3) . . . . ? C1 C6 C24 C25 103.6(4) . . . . ? C5 C6 C24 C25 -75.9(4) . . . . ? C20 C19 C25 C24 -9.5(6) . . . . ? C18 C19 C25 C24 171.4(3) . . . . ? C23 C24 C25 C19 44.5(5) . . . . ? C6 C24 C25 C19 -83.5(4) . . . . ? C22 C23 C26 O1 0.0(4) . . . . ? C24 C23 C26 O1 174.7(3) . . . . ? C22 C23 C26 C12 -179.6(4) . . . . ? C24 C23 C26 C12 -4.9(7) . . . . ? C27 O1 C26 C23 -0.6(4) . . . . ? C27 O1 C26 C12 179.0(3) . . . . ? C11 C12 C26 C23 5.8(6) . . . . ? C7 C12 C26 C23 -175.9(4) . . . . ? C11 C12 C26 O1 -173.8(3) . . . . ? C7 C12 C26 O1 4.5(5) . . . . ? C23 C22 C27 O1 -1.1(4) . . . . ? C21 C22 C27 O1 -179.4(3) . . . . ? C23 C22 C27 C28 176.8(3) . . . . ? C21 C22 C27 C28 -1.6(6) . . . . ? C26 O1 C27 C22 1.1(4) . . . . ? C26 O1 C27 C28 -177.0(3) . . . . ? C22 C27 C28 C29 18.8(5) . . . . ? O1 C27 C28 C29 -163.5(3) . . . . ? C27 C28 C29 C31 -164.2(3) . . . . ? C27 C28 C29 C33 79.4(4) . . . . ? C27 C28 C29 C30 -44.4(4) . . . . ? C20 C21 C30 C29 136.8(3) . . . . ? C22 C21 C30 C29 -40.0(4) . . . . ? C31 C29 C30 C21 177.0(3) . . . . ? C33 C29 C30 C21 -63.7(4) . . . . ? C28 C29 C30 C21 58.0(4) . . . . ? C32 O2 C31 O3 0.9(7) . . . . ? C32 O2 C31 C29 -179.5(4) . . . . ? C33 C29 C31 O3 126.1(5) . . . . ? C28 C29 C31 O3 8.8(6) . . . . ? C30 C29 C31 O3 -111.6(5) . . . . ? C33 C29 C31 O2 -53.4(4) . . . . ? C28 C29 C31 O2 -170.7(3) . . . . ? C30 C29 C31 O2 68.8(4) . . . . ? C34 O4 C33 O5 -3.1(6) . . . . ? C34 O4 C33 C29 175.9(3) . . . . ? C31 C29 C33 O5 -78.8(5) . . . . ? C28 C29 C33 O5 38.0(5) . . . . ? C30 C29 C33 O5 160.7(4) . . . . ? C31 C29 C33 O4 102.2(4) . . . . ? C28 C29 C33 O4 -141.0(3) . . . . ? C30 C29 C33 O4 -18.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.215 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.041