Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Michael S. Sherburn' _publ_contact_author_address ; Dr Michael Sherburn Research School of Chemistry Australian National University Research Road Acton ACT 2601 AUSTRALIA ; _publ_contact_author_email sherburn@rsc.anu.edu.au _publ_contact_author_fax '+61-2-6125 8114' _publ_contact_author_phone '+61-2-6125 4988' _publ_requested_journal 'Chemical Communications' _publ_section_title ; The domino intramolecular Diels-Alder approach to 16-oxasteroids ; loop_ _publ_author_name _publ_author_address 'Caig I Turner' ; School of Chemistry, University of Sydney, Sydney, NSW 2006, Australia. ; 'Rachel M. Williamson' ; Institute of Fundamental Sciences, Massey University, Private Bag 11222, Palmerston North, New Zealand ; 'Peter Turner' ; School of Chemistry, University of Sydney, Sydney, NSW 2006, Australia. ; 'Michael S. Sherburn' ; Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia. ; #======================================================================= data_mss25 _database_code_CSD 210262 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 O6' _chemical_formula_weight 400.45 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' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8232(15) _cell_length_b 8.2488(16) _cell_length_c 15.889(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.311(3) _cell_angle_gamma 90.00 _cell_volume 1023.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 872 _cell_measurement_theta_min 2.469 _cell_measurement_theta_max 26.094 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.398 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 71 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 10059 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2598 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _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^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack parameter refined to 0.0(7), so all reflections were then merged' _refine_ls_number_reflns 2598 _refine_ls_number_parameters 265 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_restrained_S_all 1.295 _refine_ls_shift/su_max 0.002 _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 0.04173(16) 0.14511(17) 0.68570(9) 0.0351(4) Uani 1 1 d . . . O2 O -0.15408(17) 0.15641(19) 0.57866(9) 0.0394(4) Uani 1 1 d . . . O3 O 0.42199(18) 0.28677(17) 0.80711(8) 0.0350(4) Uani 1 1 d . . . O4 O 0.36196(19) 0.05797(19) 0.88003(9) 0.0420(4) Uani 1 1 d . . . O5 O 0.0690(2) 0.22066(19) 0.13402(10) 0.0531(5) Uani 1 1 d . . . O6 O 0.0880(2) -0.0474(2) 0.12543(10) 0.0496(4) Uani 1 1 d . . . C1 C 0.2248(2) 0.1748(3) 0.70204(12) 0.0286(5) Uani 1 1 d . . . H1 H 0.2884 0.0696 0.7017 0.034 Uiso 1 1 calc R . . C2 C -0.0092(2) 0.1810(3) 0.60405(13) 0.0302(5) Uani 1 1 d . . . C3 C 0.1411(2) 0.2428(2) 0.56120(12) 0.0250(4) Uani 1 1 d . . . C4 C 0.2769(2) 0.2808(3) 0.62889(12) 0.0265(5) Uani 1 1 d . . . H4 H 0.2659 0.3972 0.6453 0.032 Uiso 1 1 calc R . . C5 C 0.4518(2) 0.2544(3) 0.59797(12) 0.0295(5) Uani 1 1 d . . . H5 H 0.5454 0.2333 0.6372 0.035 Uiso 1 1 calc R . . C6 C 0.4771(2) 0.2601(3) 0.51678(12) 0.0308(5) Uani 1 1 d . . . H6 H 0.5911 0.2474 0.5003 0.037 Uiso 1 1 calc R . . C7 C 0.3378(2) 0.2855(2) 0.44753(12) 0.0259(5) Uani 1 1 d . . . H7 H 0.3382 0.4026 0.4313 0.031 Uiso 1 1 calc R . . C8 C 0.1626(2) 0.2459(2) 0.47852(12) 0.0252(4) Uani 1 1 d . . . C9 C 0.0182(2) 0.2165(3) 0.41267(13) 0.0319(5) Uani 1 1 d . . . H9A H -0.0266 0.3224 0.3920 0.038 Uiso 1 1 calc R . . H9B H -0.0759 0.1595 0.4395 0.038 Uiso 1 1 calc R . . C10 C 0.0708(2) 0.1173(3) 0.33781(13) 0.0322(5) Uani 1 1 d . . . H10A H -0.0242 0.1158 0.2939 0.039 Uiso 1 1 calc R . . H10B H 0.0936 0.0041 0.3560 0.039 Uiso 1 1 calc R . . C11 C 0.2304(2) 0.1871(3) 0.30080(12) 0.0274(5) Uani 1 1 d . . . H11 H 0.2069 0.3022 0.2842 0.033 Uiso 1 1 calc R . . C12 C 0.3784(2) 0.1844(3) 0.36877(12) 0.0266(5) Uani 1 1 d . . . H12 H 0.3946 0.0693 0.3874 0.032 Uiso 1 1 calc R . . C13 C 0.5425(2) 0.2384(3) 0.33174(13) 0.0319(5) Uani 1 1 d . . . H13 H 0.6320 0.2789 0.3689 0.038 Uiso 1 1 calc R . . C14 C 0.5678(3) 0.2324(3) 0.25047(13) 0.0332(5) Uani 1 1 d . . . H14 H 0.6749 0.2693 0.2326 0.040 Uiso 1 1 calc R . . C15 C 0.4396(3) 0.1714(3) 0.18457(12) 0.0326(5) Uani 1 1 d . . . H15A H 0.4949 0.0902 0.1492 0.039 Uiso 1 1 calc R . . H15B H 0.4010 0.2626 0.1477 0.039 Uiso 1 1 calc R . . C16 C 0.2827(2) 0.0937(3) 0.22312(12) 0.0305(5) Uani 1 1 d . . . H16 H 0.3165 -0.0180 0.2420 0.037 Uiso 1 1 calc R . . C17 C 0.2446(2) 0.2502(3) 0.78865(12) 0.0325(5) Uani 1 1 d . . . H17 H 0.1739 0.3509 0.7910 0.039 Uiso 1 1 calc R . . C18 C 0.2020(3) 0.1350(3) 0.85877(14) 0.0450(7) Uani 1 1 d . . . H18A H 0.1602 0.1946 0.9076 0.054 Uiso 1 1 calc R . . H18B H 0.1144 0.0550 0.8389 0.054 Uiso 1 1 calc R . . C19 C 0.4883(3) 0.1813(3) 0.87367(13) 0.0355(5) Uani 1 1 d . . . C20 C 0.6520(3) 0.1062(3) 0.84772(16) 0.0496(7) Uani 1 1 d . . . H20A H 0.6951 0.0302 0.8914 0.074 Uiso 1 1 calc R . . H20B H 0.7372 0.1913 0.8404 0.074 Uiso 1 1 calc R . . H20C H 0.6305 0.0479 0.7944 0.074 Uiso 1 1 calc R . . C21 C 0.5117(3) 0.2769(3) 0.95482(13) 0.0508(7) Uani 1 1 d . . . H21A H 0.4020 0.3245 0.9685 0.076 Uiso 1 1 calc R . . H21B H 0.5955 0.3635 0.9479 0.076 Uiso 1 1 calc R . . H21C H 0.5529 0.2046 1.0006 0.076 Uiso 1 1 calc R . . C22 C 0.1380(3) 0.0769(3) 0.15660(13) 0.0317(5) Uani 1 1 d . . . C23 C -0.0721(3) 0.2151(3) 0.07093(15) 0.0567(8) Uani 1 1 d . . . H23A H -0.0377 0.1537 0.0219 0.085 Uiso 1 1 calc R . . H23B H -0.1034 0.3257 0.0536 0.085 Uiso 1 1 calc R . . H23C H -0.1706 0.1622 0.0946 0.085 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 0.0254(7) 0.0465(10) 0.0334(8) 0.0033(7) 0.0007(6) -0.0058(7) O2 0.0215(7) 0.0527(10) 0.0436(9) -0.0006(8) -0.0018(7) -0.0037(7) O3 0.0388(9) 0.0382(9) 0.0269(8) 0.0059(7) -0.0062(7) -0.0062(7) O4 0.0449(9) 0.0413(10) 0.0389(9) 0.0118(8) -0.0045(8) -0.0094(8) O5 0.0715(11) 0.0393(11) 0.0447(10) -0.0048(8) -0.0296(9) 0.0087(9) O6 0.0484(10) 0.0431(10) 0.0553(11) -0.0107(9) -0.0134(9) -0.0034(8) C1 0.0208(10) 0.0327(11) 0.0322(12) 0.0023(10) -0.0008(9) 0.0002(10) C2 0.0261(11) 0.0298(11) 0.0345(12) -0.0040(10) 0.0012(9) 0.0018(10) C3 0.0184(9) 0.0258(11) 0.0303(11) -0.0013(9) -0.0021(8) 0.0021(8) C4 0.0241(10) 0.0276(11) 0.0275(11) -0.0011(9) -0.0010(9) -0.0009(9) C5 0.0213(10) 0.0369(12) 0.0296(12) -0.0017(10) -0.0047(8) -0.0024(9) C6 0.0195(10) 0.0418(13) 0.0306(12) -0.0005(11) -0.0022(9) -0.0009(10) C7 0.0220(10) 0.0280(11) 0.0273(11) 0.0011(9) -0.0030(9) -0.0024(9) C8 0.0195(10) 0.0243(10) 0.0312(11) 0.0004(9) -0.0037(8) 0.0003(9) C9 0.0227(10) 0.0395(14) 0.0328(12) 0.0009(10) -0.0051(9) -0.0003(9) C10 0.0285(11) 0.0384(13) 0.0288(11) 0.0001(10) -0.0059(9) -0.0046(9) C11 0.0290(10) 0.0272(11) 0.0254(11) 0.0011(9) -0.0048(9) -0.0011(9) C12 0.0247(10) 0.0290(11) 0.0258(11) 0.0042(9) -0.0008(9) -0.0004(9) C13 0.0243(10) 0.0366(12) 0.0345(12) -0.0002(10) -0.0014(9) -0.0013(10) C14 0.0285(11) 0.0377(13) 0.0338(12) 0.0001(10) 0.0045(9) -0.0021(10) C15 0.0392(12) 0.0308(12) 0.0280(11) 0.0003(10) 0.0029(9) 0.0019(10) C16 0.0340(12) 0.0289(11) 0.0279(11) 0.0002(10) -0.0028(9) 0.0021(10) C17 0.0301(11) 0.0379(12) 0.0294(11) 0.0026(10) 0.0017(9) 0.0039(10) C18 0.0432(13) 0.0582(19) 0.0337(13) 0.0079(12) 0.0044(11) -0.0049(12) C19 0.0442(13) 0.0307(12) 0.0307(12) 0.0057(10) -0.0065(10) -0.0033(11) C20 0.0451(14) 0.0366(14) 0.0659(17) 0.0019(13) -0.0064(13) 0.0006(12) C21 0.0707(17) 0.0514(16) 0.0293(13) 0.0050(13) -0.0075(12) -0.0083(14) C22 0.0324(12) 0.0372(13) 0.0257(11) -0.0028(10) 0.0026(9) -0.0009(11) C23 0.0602(16) 0.066(2) 0.0412(15) -0.0063(13) -0.0240(13) 0.0164(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 C2 1.367(2) . ? O1 C1 1.461(2) . ? O2 C2 1.198(2) . ? O3 C17 1.434(2) . ? O3 C19 1.443(2) . ? O4 C19 1.426(3) . ? O4 C18 1.426(3) . ? O5 C22 1.343(3) . ? O5 C23 1.448(3) . ? O6 C22 1.195(3) . ? C1 C17 1.510(3) . ? C1 C4 1.529(3) . ? C1 H1 1.0000 . ? C2 C3 1.483(3) . ? C3 C8 1.334(3) . ? C3 C4 1.501(2) . ? C4 C5 1.496(3) . ? C4 H4 1.0000 . ? C5 C6 1.317(3) . ? C5 H5 0.9500 . ? C6 C7 1.518(3) . ? C6 H6 0.9500 . ? C7 C8 1.518(3) . ? C7 C12 1.552(3) . ? C7 H7 1.0000 . ? C8 C9 1.515(2) . ? C9 C10 1.520(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.523(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.530(3) . ? C11 C12 1.537(2) . ? C11 H11 1.0000 . ? C12 C13 1.510(3) . ? C12 H12 1.0000 . ? C13 C14 1.319(3) . ? C13 H13 0.9500 . ? C14 C15 1.495(3) . ? C14 H14 0.9500 . ? C15 C16 1.543(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C22 1.510(3) . ? C16 H16 1.0000 . ? C17 C18 1.516(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.501(3) . ? C19 C21 1.513(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C2 O1 C1 111.19(15) . . ? C17 O3 C19 109.03(15) . . ? C19 O4 C18 105.54(16) . . ? C22 O5 C23 115.82(18) . . ? O1 C1 C17 106.20(15) . . ? O1 C1 C4 105.22(15) . . ? C17 C1 C4 116.04(17) . . ? O1 C1 H1 109.7 . . ? C17 C1 H1 109.7 . . ? C4 C1 H1 109.7 . . ? O2 C2 O1 120.09(19) . . ? O2 C2 C3 131.55(19) . . ? O1 C2 C3 108.33(16) . . ? C8 C3 C2 127.40(17) . . ? C8 C3 C4 125.24(17) . . ? C2 C3 C4 106.88(16) . . ? C5 C4 C3 110.93(15) . . ? C5 C4 C1 117.08(16) . . ? C3 C4 C1 102.48(15) . . ? C5 C4 H4 108.7 . . ? C3 C4 H4 108.7 . . ? C1 C4 H4 108.7 . . ? C6 C5 C4 120.54(18) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 124.97(18) . . ? C5 C6 H6 117.5 . . ? C7 C6 H6 117.5 . . ? C6 C7 C8 111.03(16) . . ? C6 C7 C12 109.81(15) . . ? C8 C7 C12 112.13(15) . . ? C6 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C12 C7 H7 107.9 . . ? C3 C8 C9 123.05(17) . . ? C3 C8 C7 119.42(16) . . ? C9 C8 C7 117.50(16) . . ? C8 C9 C10 113.70(16) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 111.33(17) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C16 112.61(17) . . ? C10 C11 C12 108.90(15) . . ? C16 C11 C12 109.50(15) . . ? C10 C11 H11 108.6 . . ? C16 C11 H11 108.6 . . ? C12 C11 H11 108.6 . . ? C13 C12 C11 110.16(16) . . ? C13 C12 C7 111.94(16) . . ? C11 C12 C7 112.22(15) . . ? C13 C12 H12 107.4 . . ? C11 C12 H12 107.4 . . ? C7 C12 H12 107.4 . . ? C14 C13 C12 123.36(19) . . ? C14 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C14 C15 124.46(19) . . ? C13 C14 H14 117.8 . . ? C15 C14 H14 117.8 . . ? C14 C15 C16 112.26(17) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C22 C16 C11 112.71(16) . . ? C22 C16 C15 109.98(16) . . ? C11 C16 C15 111.54(17) . . ? C22 C16 H16 107.5 . . ? C11 C16 H16 107.5 . . ? C15 C16 H16 107.5 . . ? O3 C17 C1 108.69(15) . . ? O3 C17 C18 103.47(16) . . ? C1 C17 C18 113.32(19) . . ? O3 C17 H17 110.4 . . ? C1 C17 H17 110.4 . . ? C18 C17 H17 110.4 . . ? O4 C18 C17 103.06(17) . . ? O4 C18 H18A 111.2 . . ? C17 C18 H18A 111.2 . . ? O4 C18 H18B 111.2 . . ? C17 C18 H18B 111.2 . . ? H18A C18 H18B 109.1 . . ? O4 C19 O3 105.10(15) . . ? O4 C19 C20 109.30(19) . . ? O3 C19 C20 108.91(18) . . ? O4 C19 C21 111.19(18) . . ? O3 C19 C21 109.34(19) . . ? C20 C19 C21 112.71(19) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O6 C22 O5 122.02(18) . . ? O6 C22 C16 125.7(2) . . ? O5 C22 C16 112.30(18) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C2 O1 C1 C17 139.78(17) . . . . ? C2 O1 C1 C4 16.2(2) . . . . ? C1 O1 C2 O2 176.48(19) . . . . ? C1 O1 C2 C3 -1.7(2) . . . . ? O2 C2 C3 C8 -19.5(4) . . . . ? O1 C2 C3 C8 158.33(19) . . . . ? O2 C2 C3 C4 168.2(2) . . . . ? O1 C2 C3 C4 -14.0(2) . . . . ? C8 C3 C4 C5 -24.1(3) . . . . ? C2 C3 C4 C5 148.41(17) . . . . ? C8 C3 C4 C1 -149.8(2) . . . . ? C2 C3 C4 C1 22.7(2) . . . . ? O1 C1 C4 C5 -144.93(17) . . . . ? C17 C1 C4 C5 98.0(2) . . . . ? O1 C1 C4 C3 -23.33(19) . . . . ? C17 C1 C4 C3 -140.37(17) . . . . ? C3 C4 C5 C6 23.8(3) . . . . ? C1 C4 C5 C6 140.9(2) . . . . ? C4 C5 C6 C7 -2.8(3) . . . . ? C5 C6 C7 C8 -19.7(3) . . . . ? C5 C6 C7 C12 -144.2(2) . . . . ? C2 C3 C8 C9 12.9(3) . . . . ? C4 C3 C8 C9 -176.13(19) . . . . ? C2 C3 C8 C7 -168.92(19) . . . . ? C4 C3 C8 C7 2.0(3) . . . . ? C6 C7 C8 C3 19.4(3) . . . . ? C12 C7 C8 C3 142.70(18) . . . . ? C6 C7 C8 C9 -162.30(18) . . . . ? C12 C7 C8 C9 -39.0(2) . . . . ? C3 C8 C9 C10 -141.0(2) . . . . ? C7 C8 C9 C10 40.9(3) . . . . ? C8 C9 C10 C11 -51.1(2) . . . . ? C9 C10 C11 C16 -177.77(17) . . . . ? C9 C10 C11 C12 60.6(2) . . . . ? C10 C11 C12 C13 174.80(17) . . . . ? C16 C11 C12 C13 51.3(2) . . . . ? C10 C11 C12 C7 -59.8(2) . . . . ? C16 C11 C12 C7 176.72(16) . . . . ? C6 C7 C12 C13 -63.1(2) . . . . ? C8 C7 C12 C13 172.92(17) . . . . ? C6 C7 C12 C11 172.39(17) . . . . ? C8 C7 C12 C11 48.5(2) . . . . ? C11 C12 C13 C14 -22.0(3) . . . . ? C7 C12 C13 C14 -147.6(2) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C16 -8.0(3) . . . . ? C10 C11 C16 C22 53.1(2) . . . . ? C12 C11 C16 C22 174.46(17) . . . . ? C10 C11 C16 C15 177.44(16) . . . . ? C12 C11 C16 C15 -61.2(2) . . . . ? C14 C15 C16 C22 164.34(18) . . . . ? C14 C15 C16 C11 38.5(2) . . . . ? C19 O3 C17 C1 -111.54(19) . . . . ? C19 O3 C17 C18 9.2(2) . . . . ? O1 C1 C17 O3 -178.22(16) . . . . ? C4 C1 C17 O3 -61.7(2) . . . . ? O1 C1 C17 C18 67.3(2) . . . . ? C4 C1 C17 C18 -176.16(16) . . . . ? C19 O4 C18 C17 37.7(2) . . . . ? O3 C17 C18 O4 -28.5(2) . . . . ? C1 C17 C18 O4 89.1(2) . . . . ? C18 O4 C19 O3 -32.4(2) . . . . ? C18 O4 C19 C20 -149.14(18) . . . . ? C18 O4 C19 C21 85.8(2) . . . . ? C17 O3 C19 O4 13.6(2) . . . . ? C17 O3 C19 C20 130.58(18) . . . . ? C17 O3 C19 C21 -105.9(2) . . . . ? C23 O5 C22 O6 1.3(3) . . . . ? C23 O5 C22 C16 -179.40(19) . . . . ? C11 C16 C22 O6 -126.4(2) . . . . ? C15 C16 C22 O6 108.4(2) . . . . ? C11 C16 C22 O5 54.3(2) . . . . ? C15 C16 C22 O5 -70.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.185 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.034 #===END data_mss26 _database_code_CSD 210263 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 O6' _chemical_formula_weight 400.45 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' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.565(3) _cell_length_b 11.204(7) _cell_length_c 16.075(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.682(10) _cell_angle_gamma 90.00 _cell_volume 1002.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 966 _cell_measurement_theta_min 2.534 _cell_measurement_theta_max 28.278 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.509 _exptl_crystal_size_mid 0.238 _exptl_crystal_size_min 0.051 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 94 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.07 _diffrn_reflns_number 9792 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2503 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _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^)+(0.05P)^2^+0.0P] 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_abs_structure_details 'not reliably determined' _refine_ls_number_reflns 2503 _refine_ls_number_parameters 265 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _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 0.4170(2) 0.50448(13) 0.57045(8) 0.0230(3) Uani 1 1 d . . . O2 O 0.5539(3) 0.62075(13) 0.46812(9) 0.0276(3) Uani 1 1 d . . . O3 O 0.3236(2) 0.39003(15) 0.72739(8) 0.0281(3) Uani 1 1 d . . . O4 O -0.0375(3) 0.32906(18) 0.77944(10) 0.0393(4) Uani 1 1 d . . . O5 O 0.0146(3) 0.17671(16) 0.02535(9) 0.0378(4) Uani 1 1 d . . . O6 O -0.1840(3) 0.33858(18) 0.06675(10) 0.0415(4) Uani 1 1 d . . . C1 C 0.2268(3) 0.41591(18) 0.58241(12) 0.0202(4) Uani 1 1 d . . . H1 H 0.2901 0.3337 0.5724 0.024 Uiso 1 1 calc R . . C2 C 0.4065(3) 0.54997(18) 0.49121(13) 0.0212(4) Uani 1 1 d . . . C3 C 0.1936(3) 0.49717(17) 0.44838(12) 0.0203(4) Uani 1 1 d . . . C4 C 0.0370(3) 0.44835(18) 0.51607(12) 0.0209(4) Uani 1 1 d . . . H4 H -0.0613 0.5157 0.5382 0.025 Uiso 1 1 calc R . . C5 C -0.1324(3) 0.35384(19) 0.48529(12) 0.0240(4) Uani 1 1 d . . . H5 H -0.2085 0.3029 0.5242 0.029 Uiso 1 1 calc R . . C6 C -0.1779(3) 0.3401(2) 0.40470(13) 0.0242(4) Uani 1 1 d . . . H6 H -0.2968 0.2834 0.3888 0.029 Uiso 1 1 calc R . . C7 C -0.0541(3) 0.40826(19) 0.33629(11) 0.0214(4) Uani 1 1 d . . . H7 H -0.1745 0.4654 0.3124 0.026 Uiso 1 1 calc R . . C8 C 0.1578(3) 0.48143(17) 0.36690(12) 0.0203(4) Uani 1 1 d . . . C9 C 0.3101(4) 0.53676(18) 0.29986(12) 0.0226(4) Uani 1 1 d . . . H9A H 0.4604 0.5676 0.3254 0.027 Uiso 1 1 calc R . . H9B H 0.2224 0.6053 0.2752 0.027 Uiso 1 1 calc R . . C10 C 0.3737(3) 0.44889(18) 0.23062(12) 0.0216(4) Uani 1 1 d . . . H10A H 0.4563 0.4921 0.1855 0.026 Uiso 1 1 calc R . . H10B H 0.4854 0.3876 0.2529 0.026 Uiso 1 1 calc R . . C11 C 0.1486(3) 0.38799(18) 0.19545(11) 0.0213(4) Uani 1 1 d . . . H11 H 0.0389 0.4508 0.1724 0.026 Uiso 1 1 calc R . . C12 C 0.0172(3) 0.32156(18) 0.26533(12) 0.0209(4) Uani 1 1 d . . . H12 H -0.1345 0.2881 0.2409 0.025 Uiso 1 1 calc R . . C13 C 0.1677(4) 0.21784(18) 0.29570(13) 0.0252(4) Uani 1 1 d . . . H13 H 0.1585 0.1944 0.3524 0.030 Uiso 1 1 calc R . . C14 C 0.3122(4) 0.15874(19) 0.24537(13) 0.0277(4) Uani 1 1 d . . . H14 H 0.3970 0.0920 0.2674 0.033 Uiso 1 1 calc R . . C15 C 0.3507(4) 0.1904(2) 0.15567(13) 0.0301(5) Uani 1 1 d . . . H15A H 0.3028 0.1214 0.1208 0.036 Uiso 1 1 calc R . . H15B H 0.5245 0.2041 0.1473 0.036 Uiso 1 1 calc R . . C16 C 0.2120(3) 0.30128(19) 0.12493(12) 0.0229(4) Uani 1 1 d . . . H16 H 0.3251 0.3456 0.0882 0.028 Uiso 1 1 calc R . . C17 C 0.1390(3) 0.42716(19) 0.67050(12) 0.0230(4) Uani 1 1 d . . . H17 H 0.0912 0.5115 0.6822 0.028 Uiso 1 1 calc R . . C18 C -0.0646(4) 0.3427(2) 0.69165(13) 0.0290(5) Uani 1 1 d . . . H18A H -0.2227 0.3778 0.6769 0.035 Uiso 1 1 calc R . . H18B H -0.0471 0.2653 0.6626 0.035 Uiso 1 1 calc R . . C19 C 0.2104(3) 0.3448(2) 0.80088(12) 0.0251(4) Uani 1 1 d . . . C20 C 0.3233(5) 0.2263(3) 0.82044(18) 0.0473(7) Uani 1 1 d . . . H20A H 0.2629 0.1969 0.8737 0.071 Uiso 1 1 calc R . . H20B H 0.4982 0.2354 0.8241 0.071 Uiso 1 1 calc R . . H20C H 0.2825 0.1692 0.7763 0.071 Uiso 1 1 calc R . . C21 C 0.2257(6) 0.4337(3) 0.86996(17) 0.0538(8) Uani 1 1 d . . . H21A H 0.1596 0.5102 0.8510 0.081 Uiso 1 1 calc R . . H21B H 0.3941 0.4444 0.8868 0.081 Uiso 1 1 calc R . . H21C H 0.1334 0.4048 0.9174 0.081 Uiso 1 1 calc R . . C22 C -0.0102(4) 0.2754(2) 0.07139(12) 0.0270(5) Uani 1 1 d . . . C23 C -0.1815(5) 0.1515(3) -0.03241(15) 0.0493(7) Uani 1 1 d . . . H23A H -0.3336 0.1506 -0.0023 0.074 Uiso 1 1 calc R . . H23B H -0.1557 0.0735 -0.0584 0.074 Uiso 1 1 calc R . . H23C H -0.1876 0.2134 -0.0755 0.074 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 0.0207(7) 0.0263(7) 0.0221(7) 0.0009(6) -0.0006(5) -0.0039(6) O2 0.0284(8) 0.0262(7) 0.0283(8) 0.0014(6) -0.0005(6) -0.0079(6) O3 0.0214(7) 0.0416(9) 0.0213(7) 0.0069(7) 0.0000(5) -0.0010(6) O4 0.0265(8) 0.0633(12) 0.0283(8) 0.0132(8) 0.0032(6) -0.0053(8) O5 0.0484(10) 0.0378(9) 0.0272(8) -0.0089(7) -0.0058(7) -0.0071(8) O6 0.0312(8) 0.0562(11) 0.0368(9) -0.0102(9) -0.0091(7) 0.0029(9) C1 0.0172(9) 0.0200(9) 0.0234(9) 0.0001(8) 0.0019(7) -0.0033(7) C2 0.0211(9) 0.0200(9) 0.0225(9) -0.0017(8) 0.0009(7) 0.0007(8) C3 0.0173(8) 0.0191(9) 0.0245(10) 0.0010(8) 0.0008(7) -0.0001(8) C4 0.0186(9) 0.0235(10) 0.0205(9) -0.0019(8) 0.0008(7) 0.0002(8) C5 0.0190(9) 0.0280(11) 0.0251(10) -0.0009(8) 0.0043(7) -0.0033(8) C6 0.0171(9) 0.0270(10) 0.0286(10) -0.0058(9) 0.0025(7) -0.0056(8) C7 0.0169(8) 0.0263(10) 0.0210(9) -0.0001(8) -0.0015(7) 0.0003(8) C8 0.0176(9) 0.0191(9) 0.0242(10) 0.0001(8) 0.0008(7) 0.0016(7) C9 0.0251(9) 0.0198(9) 0.0230(10) 0.0015(8) 0.0017(7) -0.0015(8) C10 0.0216(9) 0.0218(10) 0.0216(9) 0.0019(8) 0.0019(7) -0.0021(8) C11 0.0203(9) 0.0222(9) 0.0214(9) 0.0015(8) -0.0002(7) -0.0008(8) C12 0.0182(8) 0.0229(10) 0.0217(9) -0.0020(8) -0.0009(7) -0.0033(8) C13 0.0277(10) 0.0204(10) 0.0276(10) 0.0037(8) 0.0024(8) -0.0032(8) C14 0.0285(10) 0.0193(10) 0.0352(11) 0.0048(9) -0.0003(9) -0.0001(8) C15 0.0287(11) 0.0302(11) 0.0314(11) -0.0060(9) 0.0021(9) 0.0041(9) C16 0.0223(9) 0.0267(10) 0.0197(10) -0.0020(8) 0.0023(7) -0.0027(8) C17 0.0206(9) 0.0258(10) 0.0225(10) 0.0019(8) 0.0003(7) 0.0014(8) C18 0.0227(10) 0.0385(12) 0.0257(10) 0.0052(10) 0.0013(8) -0.0028(9) C19 0.0232(9) 0.0293(11) 0.0229(10) 0.0011(9) 0.0027(7) 0.0002(8) C20 0.0429(14) 0.0476(16) 0.0516(16) 0.0155(13) 0.0107(12) 0.0141(12) C21 0.076(2) 0.0487(16) 0.0371(14) -0.0139(13) 0.0216(13) -0.0230(16) C22 0.0299(11) 0.0336(11) 0.0175(10) 0.0006(9) 0.0027(8) -0.0080(9) C23 0.0599(17) 0.0615(18) 0.0262(12) -0.0072(12) -0.0076(11) -0.0256(15) _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 C2 1.373(3) . ? O1 C1 1.465(2) . ? O2 C2 1.203(2) . ? O3 C17 1.429(2) . ? O3 C19 1.438(2) . ? O4 C18 1.426(3) . ? O4 C19 1.429(2) . ? O5 C22 1.338(3) . ? O5 C23 1.452(3) . ? O6 C22 1.200(3) . ? C1 C17 1.509(3) . ? C1 C4 1.536(3) . ? C1 H1 1.0000 . ? C2 C3 1.486(3) . ? C3 C8 1.334(3) . ? C3 C4 1.505(3) . ? C4 C5 1.498(3) . ? C4 H4 1.0000 . ? C5 C6 1.326(3) . ? C5 H5 0.9500 . ? C6 C7 1.512(3) . ? C6 H6 0.9500 . ? C7 C8 1.514(3) . ? C7 C12 1.553(3) . ? C7 H7 1.0000 . ? C8 C9 1.512(3) . ? C9 C10 1.531(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.529(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.537(3) . ? C11 C12 1.540(3) . ? C11 H11 1.0000 . ? C12 C13 1.510(3) . ? C12 H12 1.0000 . ? C13 C14 1.325(3) . ? C13 H13 0.9500 . ? C14 C15 1.503(3) . ? C14 H14 0.9500 . ? C15 C16 1.541(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C22 1.526(3) . ? C16 H16 1.0000 . ? C17 C18 1.518(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C21 1.493(3) . ? C19 C20 1.501(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C2 O1 C1 110.51(14) . . ? C17 O3 C19 108.03(14) . . ? C18 O4 C19 108.41(15) . . ? C22 O5 C23 115.6(2) . . ? O1 C1 C17 108.00(15) . . ? O1 C1 C4 103.93(15) . . ? C17 C1 C4 113.83(15) . . ? O1 C1 H1 110.3 . . ? C17 C1 H1 110.3 . . ? C4 C1 H1 110.3 . . ? O2 C2 O1 120.65(19) . . ? O2 C2 C3 131.5(2) . . ? O1 C2 C3 107.87(16) . . ? C8 C3 C2 128.03(17) . . ? C8 C3 C4 125.51(17) . . ? C2 C3 C4 105.98(16) . . ? C5 C4 C3 112.68(16) . . ? C5 C4 C1 119.15(17) . . ? C3 C4 C1 100.86(15) . . ? C5 C4 H4 107.8 . . ? C3 C4 H4 107.8 . . ? C1 C4 H4 107.8 . . ? C6 C5 C4 121.14(18) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 124.65(18) . . ? C5 C6 H6 117.7 . . ? C7 C6 H6 117.7 . . ? C6 C7 C8 113.40(16) . . ? C6 C7 C12 109.93(17) . . ? C8 C7 C12 111.85(15) . . ? C6 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C12 C7 H7 107.1 . . ? C3 C8 C9 124.56(17) . . ? C3 C8 C7 119.81(16) . . ? C9 C8 C7 115.57(16) . . ? C8 C9 C10 113.02(16) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 111.12(16) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C16 111.13(15) . . ? C10 C11 C12 109.89(16) . . ? C16 C11 C12 110.34(17) . . ? C10 C11 H11 108.5 . . ? C16 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? C13 C12 C11 109.97(16) . . ? C13 C12 C7 112.92(17) . . ? C11 C12 C7 111.17(16) . . ? C13 C12 H12 107.5 . . ? C11 C12 H12 107.5 . . ? C7 C12 H12 107.5 . . ? C14 C13 C12 121.7(2) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 124.22(19) . . ? C13 C14 H14 117.9 . . ? C15 C14 H14 117.9 . . ? C14 C15 C16 114.94(17) . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15B 108.5 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C22 C16 C11 110.15(16) . . ? C22 C16 C15 115.29(18) . . ? C11 C16 C15 113.05(17) . . ? C22 C16 H16 105.8 . . ? C11 C16 H16 105.8 . . ? C15 C16 H16 105.8 . . ? O3 C17 C1 109.74(15) . . ? O3 C17 C18 102.01(16) . . ? C1 C17 C18 114.15(17) . . ? O3 C17 H17 110.2 . . ? C1 C17 H17 110.2 . . ? C18 C17 H17 110.2 . . ? O4 C18 C17 102.60(17) . . ? O4 C18 H18A 111.2 . . ? C17 C18 H18A 111.2 . . ? O4 C18 H18B 111.2 . . ? C17 C18 H18B 111.2 . . ? H18A C18 H18B 109.2 . . ? O4 C19 O3 106.06(16) . . ? O4 C19 C21 108.0(2) . . ? O3 C19 C21 110.78(19) . . ? O4 C19 C20 110.0(2) . . ? O3 C19 C20 107.29(18) . . ? C21 C19 C20 114.5(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O6 C22 O5 122.77(19) . . ? O6 C22 C16 124.7(2) . . ? O5 C22 C16 112.37(18) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C2 O1 C1 C17 -144.05(16) . . . . ? C2 O1 C1 C4 -22.83(19) . . . . ? C1 O1 C2 O2 -177.06(17) . . . . ? C1 O1 C2 C3 3.6(2) . . . . ? O2 C2 C3 C8 26.2(3) . . . . ? O1 C2 C3 C8 -154.6(2) . . . . ? O2 C2 C3 C4 -161.6(2) . . . . ? O1 C2 C3 C4 17.7(2) . . . . ? C8 C3 C4 C5 14.3(3) . . . . ? C2 C3 C4 C5 -158.18(16) . . . . ? C8 C3 C4 C1 142.50(19) . . . . ? C2 C3 C4 C1 -30.02(19) . . . . ? O1 C1 C4 C5 155.43(16) . . . . ? C17 C1 C4 C5 -87.3(2) . . . . ? O1 C1 C4 C3 31.62(18) . . . . ? C17 C1 C4 C3 148.85(17) . . . . ? C3 C4 C5 C6 -16.3(3) . . . . ? C1 C4 C5 C6 -134.2(2) . . . . ? C4 C5 C6 C7 5.2(3) . . . . ? C5 C6 C7 C8 9.1(3) . . . . ? C5 C6 C7 C12 135.2(2) . . . . ? C2 C3 C8 C9 -12.5(3) . . . . ? C4 C3 C8 C9 176.61(18) . . . . ? C2 C3 C8 C7 170.33(18) . . . . ? C4 C3 C8 C7 -0.5(3) . . . . ? C6 C7 C8 C3 -11.3(3) . . . . ? C12 C7 C8 C3 -136.28(18) . . . . ? C6 C7 C8 C9 171.35(16) . . . . ? C12 C7 C8 C9 46.3(2) . . . . ? C3 C8 C9 C10 135.9(2) . . . . ? C7 C8 C9 C10 -46.9(2) . . . . ? C8 C9 C10 C11 52.4(2) . . . . ? C9 C10 C11 C16 179.06(16) . . . . ? C9 C10 C11 C12 -58.5(2) . . . . ? C10 C11 C12 C13 -67.3(2) . . . . ? C16 C11 C12 C13 55.6(2) . . . . ? C10 C11 C12 C7 58.5(2) . . . . ? C16 C11 C12 C7 -178.59(15) . . . . ? C6 C7 C12 C13 -54.6(2) . . . . ? C8 C7 C12 C13 72.3(2) . . . . ? C6 C7 C12 C11 -178.80(15) . . . . ? C8 C7 C12 C11 -51.9(2) . . . . ? C11 C12 C13 C14 -31.7(3) . . . . ? C7 C12 C13 C14 -156.49(19) . . . . ? C12 C13 C14 C15 2.8(3) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C10 C11 C16 C22 -160.24(16) . . . . ? C12 C11 C16 C22 77.6(2) . . . . ? C10 C11 C16 C15 69.2(2) . . . . ? C12 C11 C16 C15 -53.0(2) . . . . ? C14 C15 C16 C22 -103.6(2) . . . . ? C14 C15 C16 C11 24.4(2) . . . . ? C19 O3 C17 C1 -151.61(17) . . . . ? C19 O3 C17 C18 -30.2(2) . . . . ? O1 C1 C17 O3 -67.8(2) . . . . ? C4 C1 C17 O3 177.35(16) . . . . ? O1 C1 C17 C18 178.42(16) . . . . ? C4 C1 C17 C18 63.6(2) . . . . ? C19 O4 C18 C17 -28.6(2) . . . . ? O3 C17 C18 O4 35.5(2) . . . . ? C1 C17 C18 O4 153.83(17) . . . . ? C18 O4 C19 O3 10.5(2) . . . . ? C18 O4 C19 C21 129.3(2) . . . . ? C18 O4 C19 C20 -105.2(2) . . . . ? C17 O3 C19 O4 13.5(2) . . . . ? C17 O3 C19 C21 -103.4(2) . . . . ? C17 O3 C19 C20 131.0(2) . . . . ? C23 O5 C22 O6 1.1(3) . . . . ? C23 O5 C22 C16 -175.13(18) . . . . ? C11 C16 C22 O6 22.0(3) . . . . ? C15 C16 C22 O6 151.4(2) . . . . ? C11 C16 C22 O5 -161.82(16) . . . . ? C15 C16 C22 O5 -32.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.328 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.040