Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jonathan Burton' _publ_contact_author_address ; Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email JONATHAN.BURTON@CHEM.OX.AC.UK _publ_section_title ; The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles. ; loop_ _publ_author_name 'Jonathan Burton' 'Edward A. Anderson' 'Andrew Bond' 'Ian Collins' 'John E Davies' 'Neil Feeder' ; A.B.Holmes ; "Paul T. O'Sullivan" # Attachment 'alcohol 17 cif.cif' data_ah9909 _database_code_depnum_ccdc_archive 'CCDC 655144' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 O5 Si' _chemical_formula_sum 'C28 H46 O5 Si' _chemical_formula_weight 490.74 _chemical_absolute_configuration ; Flack parameter 0.20(17) ; 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.4300(10) _cell_length_b 16.3040(10) _cell_length_c 20.8010(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2858.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8608 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4994 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4994 _reflns_number_gt 4066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0668P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.20(17) _refine_ls_number_reflns 4994 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _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 Si1 Si -0.01906(9) 0.41035(4) 0.08693(3) 0.0318(2) Uani 1 1 d . . . O1 O -0.5049(3) 0.92909(12) -0.30197(10) 0.0479(5) Uani 1 1 d . . . O2 O 0.0473(2) 0.76127(10) -0.14560(8) 0.0297(4) Uani 1 1 d . . . O3 O 0.1822(2) 0.58130(10) -0.05963(8) 0.0250(4) Uani 1 1 d . . . O4 O -0.1504(2) 0.57575(12) -0.04245(10) 0.0454(5) Uani 1 1 d . . . H4 H -0.0897 0.5379 -0.0304 0.068 Uiso 1 1 calc R . . O5 O 0.0511(2) 0.48401(11) 0.03955(9) 0.0364(5) Uani 1 1 d . . . C1 C -0.5064(5) 0.9765(2) -0.35981(15) 0.0527(9) Uani 1 1 d . . . H1A H -0.6149 0.9948 -0.3688 0.079 Uiso 1 1 calc R . . H1B H -0.4681 0.9429 -0.3956 0.079 Uiso 1 1 calc R . . H1C H -0.4373 1.0244 -0.3547 0.079 Uiso 1 1 calc R . . C2 C -0.3625(4) 0.89739(16) -0.28250(13) 0.0342(7) Uani 1 1 d . . . C3 C -0.2223(4) 0.9037(2) -0.31604(14) 0.0441(8) Uani 1 1 d . . . H3 H -0.2196 0.9320 -0.3559 0.053 Uiso 1 1 calc R . . C4 C -0.0848(4) 0.86856(18) -0.29159(15) 0.0439(8) Uani 1 1 d . . . H4A H 0.0113 0.8734 -0.3151 0.053 Uiso 1 1 calc R . . C5 C -0.0846(4) 0.82676(16) -0.23375(12) 0.0303(6) Uani 1 1 d . . . C6 C -0.2260(4) 0.82105(17) -0.20052(14) 0.0373(7) Uani 1 1 d . . . H6 H -0.2291 0.7925 -0.1607 0.045 Uiso 1 1 calc R . . C7 C -0.3630(4) 0.85629(17) -0.22428(14) 0.0395(7) Uani 1 1 d . . . H7 H -0.4587 0.8523 -0.2004 0.047 Uiso 1 1 calc R . . C8 C 0.0666(4) 0.78676(17) -0.21094(13) 0.0357(7) Uani 1 1 d . . . H8A H 0.0913 0.7387 -0.2383 0.043 Uiso 1 1 calc R . . H8B H 0.1557 0.8261 -0.2142 0.043 Uiso 1 1 calc R . . C9 C 0.1670(3) 0.70551(15) -0.12301(12) 0.0274(6) Uani 1 1 d . . . H9 H 0.2009 0.6696 -0.1595 0.033 Uiso 1 1 calc R . . C10 C 0.3106(3) 0.75380(15) -0.09900(13) 0.0314(6) Uani 1 1 d . . . H10A H 0.3364 0.7965 -0.1312 0.038 Uiso 1 1 calc R . . H10B H 0.2807 0.7821 -0.0587 0.038 Uiso 1 1 calc R . . C11 C 0.4587(3) 0.70363(15) -0.08642(13) 0.0333(6) Uani 1 1 d . . . H11 H 0.5393 0.7047 -0.1183 0.040 Uiso 1 1 calc R . . C12 C 0.4849(2) 0.65869(11) -0.03490(9) 0.0338(6) Uani 1 1 d . . . H12 H 0.5850 0.6324 -0.0309 0.041 Uiso 1 1 calc R . . C13 C 0.3651(2) 0.64640(11) 0.01831(9) 0.0320(6) Uani 1 1 d R . . H13A H 0.3003 0.6966 0.0234 0.038 Uiso 1 1 calc R . . H13B H 0.4210 0.6360 0.0594 0.038 Uiso 1 1 calc R . . C14 C 0.2572(3) 0.57334(15) 0.00220(12) 0.0273(6) Uani 1 1 d . . . H14 H 0.3272 0.5239 -0.0002 0.033 Uiso 1 1 calc R . . C15 C 0.0853(3) 0.65242(14) -0.07192(12) 0.0260(6) Uani 1 1 d . . . H15 H 0.0728 0.6848 -0.0314 0.031 Uiso 1 1 calc R . . C16 C -0.0770(3) 0.62052(16) -0.09358(13) 0.0319(6) Uani 1 1 d . . . H16 H -0.1454 0.6690 -0.1036 0.038 Uiso 1 1 calc R . . C17 C -0.0659(4) 0.56921(18) -0.15261(15) 0.0448(8) Uani 1 1 d . . . H17 H -0.0143 0.5176 -0.1490 0.054 Uiso 1 1 calc R . . C18 C -0.1216(5) 0.5895(2) -0.20899(17) 0.0626(10) Uani 1 1 d . . . H18A H -0.1741 0.6406 -0.2146 0.075 Uiso 1 1 calc R . . H18B H -0.1097 0.5532 -0.2444 0.075 Uiso 1 1 calc R . . C19 C 0.1381(4) 0.55699(16) 0.05493(12) 0.0335(7) Uani 1 1 d . . . H19A H 0.1936 0.5499 0.0965 0.040 Uiso 1 1 calc R . . H19B H 0.0644 0.6040 0.0589 0.040 Uiso 1 1 calc R . . C20 C 0.1023(4) 0.4067(2) 0.16274(14) 0.0439(8) Uani 1 1 d . . . H20 H 0.1035 0.4638 0.1804 0.053 Uiso 1 1 calc R . . C21 C 0.2748(5) 0.3831(3) 0.1511(2) 0.0787(13) Uani 1 1 d . . . H21A H 0.3183 0.4168 0.1163 0.118 Uiso 1 1 calc R . . H21B H 0.2808 0.3251 0.1391 0.118 Uiso 1 1 calc R . . H21C H 0.3363 0.3924 0.1904 0.118 Uiso 1 1 calc R . . C22 C 0.0318(5) 0.3518(3) 0.21556(16) 0.0707(11) Uani 1 1 d . . . H22A H -0.0758 0.3704 0.2258 0.106 Uiso 1 1 calc R . . H22B H 0.0982 0.3550 0.2542 0.106 Uiso 1 1 calc R . . H22C H 0.0281 0.2949 0.2004 0.106 Uiso 1 1 calc R . . C23 C 0.0053(4) 0.31493(16) 0.03777(14) 0.0448(8) Uani 1 1 d . . . H23 H 0.1201 0.2998 0.0402 0.054 Uiso 1 1 calc R . . C24 C -0.0339(5) 0.3260(2) -0.03410(15) 0.0586(10) Uani 1 1 d . . . H24A H 0.0263 0.3726 -0.0513 0.088 Uiso 1 1 calc R . . H24B H -0.1477 0.3365 -0.0391 0.088 Uiso 1 1 calc R . . H24C H -0.0051 0.2761 -0.0576 0.088 Uiso 1 1 calc R . . C25 C -0.0884(5) 0.24121(18) 0.06485(19) 0.0656(11) Uani 1 1 d . . . H25A H -0.0533 0.2299 0.1089 0.098 Uiso 1 1 calc R . . H25B H -0.0695 0.1929 0.0379 0.098 Uiso 1 1 calc R . . H25C H -0.2020 0.2541 0.0650 0.098 Uiso 1 1 calc R . . C26 C -0.2329(4) 0.43366(17) 0.10650(14) 0.0369(7) Uani 1 1 d . . . H26 H -0.2697 0.3918 0.1383 0.044 Uiso 1 1 calc R . . C27 C -0.2462(5) 0.51784(18) 0.13840(19) 0.0574(10) Uani 1 1 d . . . H27A H -0.1799 0.5191 0.1771 0.086 Uiso 1 1 calc R . . H27B H -0.3569 0.5282 0.1502 0.086 Uiso 1 1 calc R . . H27C H -0.2103 0.5602 0.1083 0.086 Uiso 1 1 calc R . . C28 C -0.3441(4) 0.4289(2) 0.04766(17) 0.0548(9) Uani 1 1 d . . . H28A H -0.3454 0.3727 0.0311 0.082 Uiso 1 1 calc R . . H28B H -0.3058 0.4662 0.0141 0.082 Uiso 1 1 calc R . . H28C H -0.4516 0.4449 0.0604 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0302(4) 0.0328(4) 0.0324(4) 0.0077(3) 0.0013(3) -0.0011(3) O1 0.0392(13) 0.0569(12) 0.0475(11) 0.0186(10) -0.0005(11) 0.0107(11) O2 0.0322(11) 0.0322(9) 0.0247(9) 0.0064(7) 0.0032(9) 0.0086(8) O3 0.0245(10) 0.0241(8) 0.0265(9) -0.0005(7) -0.0035(8) 0.0026(8) O4 0.0262(11) 0.0539(13) 0.0560(13) 0.0236(11) 0.0006(10) -0.0031(10) O5 0.0391(13) 0.0386(10) 0.0314(10) 0.0105(8) -0.0051(9) -0.0114(9) C1 0.049(2) 0.0596(19) 0.0492(18) 0.0197(15) -0.0009(18) 0.0163(17) C2 0.0326(17) 0.0340(14) 0.0362(15) 0.0038(12) -0.0033(14) 0.0004(12) C3 0.041(2) 0.0564(19) 0.0346(16) 0.0203(15) 0.0005(14) 0.0041(16) C4 0.0305(18) 0.0595(18) 0.0417(17) 0.0190(14) 0.0043(15) -0.0021(15) C5 0.0330(18) 0.0327(14) 0.0251(14) 0.0019(11) -0.0004(13) -0.0016(12) C6 0.042(2) 0.0388(15) 0.0310(15) 0.0099(12) 0.0035(15) 0.0027(14) C7 0.0335(18) 0.0465(16) 0.0383(17) 0.0097(13) 0.0069(15) 0.0055(14) C8 0.0389(18) 0.0414(15) 0.0268(14) 0.0082(12) 0.0037(14) 0.0015(13) C9 0.0278(16) 0.0266(13) 0.0279(14) 0.0014(10) 0.0020(12) 0.0032(12) C10 0.0327(17) 0.0278(13) 0.0336(15) 0.0046(12) 0.0020(13) -0.0041(12) C11 0.0253(16) 0.0367(14) 0.0380(15) -0.0011(12) 0.0023(14) -0.0076(12) C12 0.0220(16) 0.0365(13) 0.0428(15) -0.0037(12) -0.0038(14) -0.0055(12) C13 0.0304(17) 0.0363(14) 0.0294(14) 0.0012(11) -0.0044(13) -0.0062(13) C14 0.0263(15) 0.0287(14) 0.0269(13) 0.0028(11) -0.0066(12) -0.0001(11) C15 0.0257(15) 0.0249(12) 0.0274(14) 0.0013(10) 0.0021(12) 0.0034(11) C16 0.0234(15) 0.0336(13) 0.0386(15) 0.0098(12) -0.0015(14) -0.0005(11) C17 0.0330(18) 0.0451(17) 0.0561(19) -0.0041(15) -0.0142(16) -0.0051(13) C18 0.065(2) 0.069(2) 0.053(2) -0.0119(19) -0.0166(19) -0.008(2) C19 0.0357(17) 0.0361(14) 0.0288(14) 0.0031(12) -0.0028(14) -0.0070(12) C20 0.0444(19) 0.0503(17) 0.0370(16) 0.0135(14) -0.0023(14) -0.0028(16) C21 0.038(2) 0.129(4) 0.069(3) 0.044(3) -0.009(2) 0.000(2) C22 0.057(3) 0.111(3) 0.044(2) 0.036(2) 0.000(2) -0.010(2) C23 0.046(2) 0.0394(15) 0.0487(17) 0.0030(13) 0.0071(17) 0.0023(15) C24 0.071(3) 0.059(2) 0.0459(18) -0.0098(15) 0.005(2) 0.0011(19) C25 0.091(3) 0.0350(16) 0.071(2) -0.0001(16) 0.011(2) -0.0076(18) C26 0.0325(18) 0.0352(15) 0.0430(16) 0.0094(13) 0.0068(14) -0.0025(13) C27 0.056(2) 0.0440(18) 0.073(2) 0.0041(17) 0.024(2) 0.0078(16) C28 0.0331(19) 0.065(2) 0.066(2) 0.0143(17) -0.0030(18) -0.0048(17) _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 Si1 O5 1.6625(18) . ? Si1 C23 1.873(3) . ? Si1 C20 1.881(3) . ? Si1 C26 1.887(3) . ? O1 C2 1.368(3) . ? O1 C1 1.430(3) . ? O2 C8 1.430(3) . ? O2 C9 1.437(3) . ? O3 C14 1.439(3) . ? O3 C15 1.442(3) . ? O4 C16 1.431(3) . ? O4 H4 0.8400 . ? O5 C19 1.434(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.376(4) . ? C2 C7 1.384(4) . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 H4A 0.9500 . ? C5 C6 1.381(4) . ? C5 C8 1.508(4) . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.528(4) . ? C9 C15 1.534(3) . ? C9 H9 1.0000 . ? C10 C11 1.515(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.317(3) . ? C11 H11 0.9500 . ? C12 C13 1.5113 . ? C12 H12 0.9500 . ? C13 C14 1.536(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.511(4) . ? C14 H14 1.0000 . ? C15 C16 1.531(4) . ? C15 H15 1.0000 . ? C16 C17 1.489(4) . ? C16 H16 1.0000 . ? C17 C18 1.306(4) . ? C17 H17 0.9500 . ? C18 H18A 0.9500 . ? C18 H18B 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.523(5) . ? C20 C22 1.537(4) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.542(4) . ? C23 C25 1.545(4) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.528(4) . ? C26 C28 1.544(4) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 Si1 C23 103.74(12) . . ? O5 Si1 C20 109.03(12) . . ? C23 Si1 C20 111.84(15) . . ? O5 Si1 C26 108.81(12) . . ? C23 Si1 C26 112.95(15) . . ? C20 Si1 C26 110.19(14) . . ? C2 O1 C1 117.5(2) . . ? C8 O2 C9 114.5(2) . . ? C14 O3 C15 118.69(18) . . ? C16 O4 H4 109.5 . . ? C19 O5 Si1 130.49(16) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 125.1(2) . . ? O1 C2 C7 116.1(3) . . ? C3 C2 C7 118.8(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 121.5(3) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C6 C5 C4 117.9(3) . . ? C6 C5 C8 122.9(2) . . ? C4 C5 C8 119.2(3) . . ? C5 C6 C7 121.0(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 120.8(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O2 C8 C5 109.2(2) . . ? O2 C8 H8A 109.8 . . ? C5 C8 H8A 109.8 . . ? O2 C8 H8B 109.8 . . ? C5 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O2 C9 C10 109.71(19) . . ? O2 C9 C15 105.5(2) . . ? C10 C9 C15 114.8(2) . . ? O2 C9 H9 108.9 . . ? C10 C9 H9 108.9 . . ? C15 C9 H9 108.9 . . ? C11 C10 C9 115.5(2) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 125.4(2) . . ? C12 C11 H11 117.3 . . ? C10 C11 H11 117.3 . . ? C11 C12 C13 123.91(16) . . ? C11 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 109.80(12) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? O3 C14 C19 111.9(2) . . ? O3 C14 C13 112.66(19) . . ? C19 C14 C13 111.9(2) . . ? O3 C14 H14 106.7 . . ? C19 C14 H14 106.7 . . ? C13 C14 H14 106.7 . . ? O3 C15 C16 106.59(19) . . ? O3 C15 C9 108.8(2) . . ? C16 C15 C9 112.9(2) . . ? O3 C15 H15 109.5 . . ? C16 C15 H15 109.5 . . ? C9 C15 H15 109.5 . . ? O4 C16 C17 110.7(2) . . ? O4 C16 C15 109.9(2) . . ? C17 C16 C15 112.2(2) . . ? O4 C16 H16 107.9 . . ? C17 C16 H16 107.9 . . ? C15 C16 H16 107.9 . . ? C18 C17 C16 125.2(3) . . ? C18 C17 H17 117.4 . . ? C16 C17 H17 117.4 . . ? C17 C18 H18A 120.0 . . ? C17 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? O5 C19 C14 108.9(2) . . ? O5 C19 H19A 109.9 . . ? C14 C19 H19A 109.9 . . ? O5 C19 H19B 109.9 . . ? C14 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? C21 C20 C22 109.6(3) . . ? C21 C20 Si1 113.2(2) . . ? C22 C20 Si1 114.0(2) . . ? C21 C20 H20 106.5 . . ? C22 C20 H20 106.5 . . ? Si1 C20 H20 106.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C25 109.6(3) . . ? C24 C23 Si1 114.1(2) . . ? C25 C23 Si1 113.0(2) . . ? C24 C23 H23 106.5 . . ? C25 C23 H23 106.5 . . ? Si1 C23 H23 106.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C28 110.2(3) . . ? C27 C26 Si1 110.2(2) . . ? C28 C26 Si1 113.5(2) . . ? C27 C26 H26 107.6 . . ? C28 C26 H26 107.6 . . ? Si1 C26 H26 107.6 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 Si1 O5 C19 -144.4(3) . . . . ? C20 Si1 O5 C19 -25.1(3) . . . . ? C26 Si1 O5 C19 95.1(3) . . . . ? C1 O1 C2 C3 -3.9(4) . . . . ? C1 O1 C2 C7 176.0(3) . . . . ? O1 C2 C3 C4 -179.7(3) . . . . ? C7 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C3 C4 C5 C8 177.4(3) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C8 C5 C6 C7 -177.7(3) . . . . ? C5 C6 C7 C2 0.8(5) . . . . ? O1 C2 C7 C6 179.2(3) . . . . ? C3 C2 C7 C6 -0.9(5) . . . . ? C9 O2 C8 C5 165.9(2) . . . . ? C6 C5 C8 O2 -13.5(4) . . . . ? C4 C5 C8 O2 169.0(2) . . . . ? C8 O2 C9 C10 85.4(3) . . . . ? C8 O2 C9 C15 -150.4(2) . . . . ? O2 C9 C10 C11 -168.0(2) . . . . ? C15 C9 C10 C11 73.3(3) . . . . ? C9 C10 C11 C12 -79.2(3) . . . . ? C10 C11 C12 C13 3.8(3) . . . . ? C11 C12 C13 C14 87.5(2) . . . . ? C15 O3 C14 C19 69.5(3) . . . . ? C15 O3 C14 C13 -57.6(3) . . . . ? C12 C13 C14 O3 -54.5(2) . . . . ? C12 C13 C14 C19 178.39(16) . . . . ? C14 O3 C15 C16 -125.5(2) . . . . ? C14 O3 C15 C9 112.5(2) . . . . ? O2 C9 C15 O3 164.43(18) . . . . ? C10 C9 C15 O3 -74.6(3) . . . . ? O2 C9 C15 C16 46.3(3) . . . . ? C10 C9 C15 C16 167.3(2) . . . . ? O3 C15 C16 O4 64.1(2) . . . . ? C9 C15 C16 O4 -176.6(2) . . . . ? O3 C15 C16 C17 -59.6(3) . . . . ? C9 C15 C16 C17 59.8(3) . . . . ? O4 C16 C17 C18 124.9(3) . . . . ? C15 C16 C17 C18 -111.9(4) . . . . ? Si1 O5 C19 C14 144.2(2) . . . . ? O3 C14 C19 O5 57.6(3) . . . . ? C13 C14 C19 O5 -174.90(19) . . . . ? O5 Si1 C20 C21 -64.1(3) . . . . ? C23 Si1 C20 C21 50.1(3) . . . . ? C26 Si1 C20 C21 176.6(3) . . . . ? O5 Si1 C20 C22 169.7(2) . . . . ? C23 Si1 C20 C22 -76.1(3) . . . . ? C26 Si1 C20 C22 50.4(3) . . . . ? O5 Si1 C23 C24 -39.9(3) . . . . ? C20 Si1 C23 C24 -157.2(3) . . . . ? C26 Si1 C23 C24 77.8(3) . . . . ? O5 Si1 C23 C25 -166.0(3) . . . . ? C20 Si1 C23 C25 76.6(3) . . . . ? C26 Si1 C23 C25 -48.4(3) . . . . ? O5 Si1 C26 C27 -57.6(2) . . . . ? C23 Si1 C26 C27 -172.2(2) . . . . ? C20 Si1 C26 C27 61.9(3) . . . . ? O5 Si1 C26 C28 66.5(2) . . . . ? C23 Si1 C26 C28 -48.1(2) . . . . ? C20 Si1 C26 C28 -174.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.417 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.123 # Attachment 'lactone 41 cif.cif' data_ah9912 _database_code_depnum_ccdc_archive 'CCDC 655145' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H26 O4' _chemical_formula_sum 'C19 H26 O4' _chemical_formula_weight 318.40 _chemical_absolute_configuration ; 1385 Friedel pairs were averaged for the refinement ; 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8190(4) _cell_length_b 5.37100(10) _cell_length_c 15.6400(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.8090(16) _cell_angle_gamma 90.00 _cell_volume 886.21(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11472 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ? _exptl_special_details ; The -Ph ring is disordered over two sites: a common, isotropic displacement parameter was assigned to the carbon atoms of this group. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 19185 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1746 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.1087P)^2^+0.3495P] 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 SHELXL _refine_ls_extinction_coef 0.19(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 1746 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _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 0.6253(2) 0.2338(5) -0.35502(17) 0.0421(7) Uani 1 1 d . . . O2 O 0.7398(2) 0.5393(5) -0.27517(15) 0.0368(6) Uani 1 1 d . . . O3 O 0.5526(3) 0.5418(6) -0.49207(17) 0.0502(8) Uani 1 1 d . . . H100 H 0.5017 0.6524 -0.5162 0.075 Uiso 1 1 calc R . . O4 O 0.7426(3) 0.3915(7) -0.01905(18) 0.0577(9) Uani 1 1 d . . . C1 C 0.6618(3) 0.4469(7) -0.3475(2) 0.0341(8) Uani 1 1 d . . . C2 C 0.6360(4) 0.6429(8) -0.4172(2) 0.0418(9) Uani 1 1 d . . . H2A H 0.5959 0.7909 -0.3956 0.050 Uiso 1 1 calc R . . C3 C 0.7672(4) 0.7162(8) -0.4343(2) 0.0470(10) Uani 1 1 d . . . H3A H 0.7545 0.8069 -0.4906 0.056 Uiso 1 1 calc R . . H3B H 0.8102 0.8303 -0.3873 0.056 Uiso 1 1 calc R . . C4 C 0.8522(3) 0.4920(8) -0.4374(2) 0.0427(9) Uani 1 1 d . . . C5 C 0.9287(3) 0.3842(8) -0.3685(2) 0.0409(9) Uani 1 1 d . . . H5A H 0.9734 0.2437 -0.3829 0.049 Uiso 1 1 calc R . . C6 C 0.9574(3) 0.4463(8) -0.2706(3) 0.0400(9) Uani 1 1 d . . . H6A H 1.0276 0.3323 -0.2422 0.048 Uiso 1 1 calc R . . C7 C 0.8433(3) 0.3793(8) -0.2311(2) 0.0358(8) Uani 1 1 d . A . H7A H 0.8195 0.2018 -0.2453 0.043 Uiso 1 1 calc R . . C8 C 0.8384(5) 0.3793(12) -0.5273(3) 0.0617(13) Uani 1 1 d . . . H8A H 0.8953 0.2359 -0.5238 0.093 Uiso 1 1 calc R . . H8B H 0.8604 0.5038 -0.5673 0.093 Uiso 1 1 calc R . . H8C H 0.7506 0.3249 -0.5492 0.093 Uiso 1 1 calc R . . C9 C 1.0067(4) 0.7094(9) -0.2493(3) 0.0501(10) Uani 1 1 d . . . H9A H 1.0757 0.7427 -0.2792 0.075 Uiso 1 1 calc R . . H9B H 1.0384 0.7261 -0.1859 0.075 Uiso 1 1 calc R . . H9C H 0.9379 0.8288 -0.2693 0.075 Uiso 1 1 calc R . . C10 C 0.8584(3) 0.4194(8) -0.1328(2) 0.0397(9) Uani 1 1 d . . . H10A H 0.8609 0.6023 -0.1206 0.048 Uiso 1 1 calc R A . C11 C 0.9807(4) 0.3006(9) -0.0807(3) 0.0555(12) Uani 1 1 d . A . H11A H 0.9817 0.3079 -0.0179 0.083 Uiso 1 1 calc R . . H11B H 1.0539 0.3914 -0.0921 0.083 Uiso 1 1 calc R . . H11C H 0.9848 0.1265 -0.0986 0.083 Uiso 1 1 calc R . . C12 C 0.7433(4) 0.3066(10) -0.1053(3) 0.0538(12) Uani 1 1 d . A . H12A H 0.6644 0.3588 -0.1467 0.065 Uiso 1 1 calc R . . H12B H 0.7483 0.1226 -0.1061 0.065 Uiso 1 1 calc R . . C13' C 0.6608(12) 0.254(3) 0.0208(9) 0.0571(18) Uiso 0.45 1 d P A 2 H13C H 0.6959 0.0863 0.0371 0.069 Uiso 0.45 1 calc PR A 2 H13D H 0.5768 0.2360 -0.0196 0.069 Uiso 0.45 1 calc PR A 2 C14' C 0.6484(7) 0.4082(13) 0.1071(4) 0.0564(7) Uiso 0.45 1 d PG A 2 C15' C 0.5821(6) 0.2923(10) 0.1627(4) 0.0564(7) Uiso 0.45 1 d PG A 2 H15' H 0.5461 0.1322 0.1484 0.068 Uiso 0.45 1 calc PR A 2 C16' C 0.5686(7) 0.4106(12) 0.2391(4) 0.0564(7) Uiso 0.45 1 d PG A 2 H16' H 0.5234 0.3314 0.2771 0.068 Uiso 0.45 1 calc PR A 2 C17' C 0.6214(7) 0.6448(13) 0.2600(4) 0.0564(7) Uiso 0.45 1 d PG A 2 H17' H 0.6121 0.7257 0.3123 0.068 Uiso 0.45 1 calc PR A 2 C18' C 0.6876(6) 0.7608(11) 0.2045(4) 0.0564(7) Uiso 0.45 1 d PG A 2 H18' H 0.7236 0.9208 0.2187 0.068 Uiso 0.45 1 calc PR A 2 C19' C 0.7011(6) 0.6424(13) 0.1280(4) 0.0564(7) Uiso 0.45 1 d PG A 2 H19' H 0.7463 0.7217 0.0900 0.068 Uiso 0.45 1 calc PR A 2 C13 C 0.6356(10) 0.290(2) 0.0084(7) 0.0571(18) Uiso 0.55 1 d P A 1 H13A H 0.6436 0.1067 0.0112 0.069 Uiso 0.55 1 calc PR A 1 H13B H 0.5578 0.3310 -0.0362 0.069 Uiso 0.55 1 calc PR A 1 C14 C 0.6218(5) 0.3822(12) 0.0930(3) 0.0564(7) Uiso 0.55 1 d PG A 1 C15 C 0.5215(5) 0.3018(11) 0.1282(3) 0.0564(7) Uiso 0.55 1 d PG A 1 H15 H 0.4620 0.1856 0.0970 0.068 Uiso 0.55 1 calc PR A 1 C16 C 0.5083(5) 0.3914(11) 0.2091(3) 0.0564(7) Uiso 0.55 1 d PG A 1 H16 H 0.4398 0.3364 0.2332 0.068 Uiso 0.55 1 calc PR A 1 C17 C 0.5953(5) 0.5613(12) 0.2547(3) 0.0564(7) Uiso 0.55 1 d PG A 1 H17 H 0.5863 0.6226 0.3100 0.068 Uiso 0.55 1 calc PR A 1 C18 C 0.6956(5) 0.6418(11) 0.2195(3) 0.0564(7) Uiso 0.55 1 d PG A 1 H18 H 0.7551 0.7579 0.2507 0.068 Uiso 0.55 1 calc PR A 1 C19 C 0.7088(5) 0.5522(12) 0.1386(3) 0.0564(7) Uiso 0.55 1 d PG A 1 H19 H 0.7774 0.6071 0.1146 0.068 Uiso 0.55 1 calc PR A 1 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 0.0456(14) 0.0394(16) 0.0408(14) -0.0004(12) 0.0084(11) -0.0057(12) O2 0.0378(13) 0.0336(13) 0.0367(12) -0.0050(11) 0.0034(10) 0.0072(11) O3 0.0558(16) 0.0381(15) 0.0462(15) -0.0034(13) -0.0108(12) 0.0040(14) O4 0.0626(17) 0.072(2) 0.0439(15) -0.0043(16) 0.0236(13) -0.0090(17) C1 0.0335(16) 0.0324(19) 0.0370(19) -0.0073(15) 0.0092(14) 0.0037(16) C2 0.045(2) 0.035(2) 0.0400(19) -0.0055(16) -0.0017(15) 0.0014(17) C3 0.063(2) 0.0342(19) 0.041(2) 0.0057(18) 0.0038(17) -0.008(2) C4 0.045(2) 0.045(2) 0.0401(19) -0.0001(18) 0.0145(16) -0.0117(18) C5 0.0420(18) 0.042(2) 0.043(2) -0.0048(18) 0.0182(16) -0.0011(17) C6 0.0371(18) 0.042(2) 0.0407(19) -0.0031(16) 0.0079(15) 0.0033(17) C7 0.0360(17) 0.0346(18) 0.0360(18) -0.0029(16) 0.0061(14) 0.0047(15) C8 0.070(3) 0.082(4) 0.037(2) 0.001(2) 0.0201(19) -0.004(3) C9 0.050(2) 0.049(2) 0.050(2) -0.003(2) 0.0067(17) -0.010(2) C10 0.0396(18) 0.045(2) 0.0344(18) -0.0012(17) 0.0073(14) 0.0049(17) C11 0.064(3) 0.059(3) 0.041(2) 0.000(2) 0.0059(19) 0.014(2) C12 0.058(2) 0.065(3) 0.040(2) -0.001(2) 0.0134(18) -0.008(2) _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 C1 1.208(5) . ? O2 C1 1.347(4) . ? O2 C7 1.458(4) . ? O3 C2 1.418(4) . ? O3 H100 0.8400 . ? O4 C13' 1.400(15) . ? O4 C12 1.426(5) . ? O4 C13 1.429(12) . ? C1 C2 1.496(5) . ? C2 C3 1.552(6) . ? C2 H2A 1.0000 . ? C3 C4 1.522(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.337(5) . ? C4 C8 1.507(6) . ? C5 C6 1.531(5) . ? C5 H5A 0.9500 . ? C6 C9 1.521(6) . ? C6 C7 1.539(5) . ? C6 H6A 1.0000 . ? C7 C10 1.525(5) . ? C7 H7A 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.529(6) . ? C10 C11 1.531(5) . ? C10 H10A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13' C14' 1.614(15) . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' C15' 1.3900 . ? C14' C19' 1.3900 . ? C15' C16' 1.3900 . ? C15' H15' 0.9500 . ? C16' C17' 1.3900 . ? C16' H16' 0.9500 . ? C17' C18' 1.3900 . ? C17' H17' 0.9500 . ? C18' C19' 1.3900 . ? C18' H18' 0.9500 . ? C19' H19' 0.9500 . ? C13 C14 1.451(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.3900 . ? C14 C19 1.3900 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C7 116.9(3) . . ? C2 O3 H100 109.5 . . ? C13' O4 C12 112.9(7) . . ? C13' O4 C13 14.4(9) . . ? C12 O4 C13 109.7(5) . . ? O1 C1 O2 124.1(3) . . ? O1 C1 C2 126.3(3) . . ? O2 C1 C2 109.5(3) . . ? O3 C2 C1 108.3(3) . . ? O3 C2 C3 113.2(3) . . ? C1 C2 C3 105.9(3) . . ? O3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C4 C3 C2 112.8(3) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C8 119.6(4) . . ? C5 C4 C3 125.9(3) . . ? C8 C4 C3 114.4(4) . . ? C4 C5 C6 131.7(4) . . ? C4 C5 H5A 114.2 . . ? C6 C5 H5A 114.2 . . ? C9 C6 C5 113.8(4) . . ? C9 C6 C7 113.8(3) . . ? C5 C6 C7 110.3(3) . . ? C9 C6 H6A 106.1 . . ? C5 C6 H6A 106.1 . . ? C7 C6 H6A 106.1 . . ? O2 C7 C10 107.0(3) . . ? O2 C7 C6 105.8(3) . . ? C10 C7 C6 117.1(3) . . ? O2 C7 H7A 108.9 . . ? C10 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 C12 108.4(3) . . ? C7 C10 C11 111.4(3) . . ? C12 C10 C11 110.3(4) . . ? C7 C10 H10A 108.9 . . ? C12 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 C10 108.4(3) . . ? O4 C12 H12A 110.0 . . ? C10 C12 H12A 110.0 . . ? O4 C12 H12B 110.0 . . ? C10 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? O4 C13' C14' 106.3(10) . . ? O4 C13' H13C 110.5 . . ? C14' C13' H13C 110.5 . . ? O4 C13' H13D 110.5 . . ? C14' C13' H13D 110.5 . . ? H13C C13' H13D 108.7 . . ? C15' C14' C19' 120.0 . . ? C15' C14' C13' 116.3(7) . . ? C19' C14' C13' 123.7(7) . . ? C14' C15' C16' 120.0 . . ? C14' C15' H15' 120.0 . . ? C16' C15' H15' 120.0 . . ? C15' C16' C17' 120.0 . . ? C15' C16' H16' 120.0 . . ? C17' C16' H16' 120.0 . . ? C18' C17' C16' 120.0 . . ? C18' C17' H17' 120.0 . . ? C16' C17' H17' 120.0 . . ? C17' C18' C19' 120.0 . . ? C17' C18' H18' 120.0 . . ? C19' C18' H18' 120.0 . . ? C18' C19' C14' 120.0 . . ? C18' C19' H19' 120.0 . . ? C14' C19' H19' 120.0 . . ? O4 C13 C14 113.5(8) . . ? O4 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? O4 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C19 120.0 . . ? C15 C14 C13 120.2(5) . . ? C19 C14 C13 119.8(5) . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C14 120.0 . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O2 C1 O1 40.0(5) . . . . ? C7 O2 C1 C2 -136.3(3) . . . . ? O1 C1 C2 O3 4.5(5) . . . . ? O2 C1 C2 O3 -179.3(3) . . . . ? O1 C1 C2 C3 -117.2(4) . . . . ? O2 C1 C2 C3 59.0(4) . . . . ? O3 C2 C3 C4 -76.1(4) . . . . ? C1 C2 C3 C4 42.4(4) . . . . ? C2 C3 C4 C5 -86.3(4) . . . . ? C2 C3 C4 C8 89.6(4) . . . . ? C8 C4 C5 C6 -176.9(4) . . . . ? C3 C4 C5 C6 -1.3(7) . . . . ? C4 C5 C6 C9 -57.2(5) . . . . ? C4 C5 C6 C7 72.1(6) . . . . ? C1 O2 C7 C10 -142.2(3) . . . . ? C1 O2 C7 C6 92.3(3) . . . . ? C9 C6 C7 O2 66.0(4) . . . . ? C5 C6 C7 O2 -63.4(4) . . . . ? C9 C6 C7 C10 -53.2(5) . . . . ? C5 C6 C7 C10 177.5(3) . . . . ? O2 C7 C10 C12 69.7(4) . . . . ? C6 C7 C10 C12 -171.8(4) . . . . ? O2 C7 C10 C11 -168.7(3) . . . . ? C6 C7 C10 C11 -50.3(5) . . . . ? C13' O4 C12 C10 -165.3(7) . . . . ? C13 O4 C12 C10 179.7(6) . . . . ? C7 C10 C12 O4 -167.1(3) . . . . ? C11 C10 C12 O4 70.7(5) . . . . ? C12 O4 C13' C14' -168.1(6) . . . . ? C13 O4 C13' C14' -88(4) . . . . ? O4 C13' C14' C15' -173.1(6) . . . . ? O4 C13' C14' C19' 5.9(11) . . . . ? C19' C14' C15' C16' 0.0 . . . . ? C13' C14' C15' C16' 179.1(7) . . . . ? C14' C15' C16' C17' 0.0 . . . . ? C15' C16' C17' C18' 0.0 . . . . ? C16' C17' C18' C19' 0.0 . . . . ? C17' C18' C19' C14' 0.0 . . . . ? C15' C14' C19' C18' 0.0 . . . . ? C13' C14' C19' C18' -179.0(8) . . . . ? C13' O4 C13 C14 79(4) . . . . ? C12 O4 C13 C14 -175.5(7) . . . . ? O4 C13 C14 C15 179.6(5) . . . . ? O4 C13 C14 C19 0.0(11) . . . . ? C19 C14 C15 C16 0.0 . . . . ? C13 C14 C15 C16 -179.7(8) . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C14 0.0 . . . . ? C15 C14 C19 C18 0.0 . . . . ? C13 C14 C19 C18 179.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.587 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.108 # Attachment 'carbonate 62 cif.cif' data_ah9917 _database_code_depnum_ccdc_archive 'CCDC 655146' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 O5' _chemical_formula_sum 'C12 H14 O5' _chemical_formula_weight 238.23 _chemical_absolute_configuration ; 1288 friedel pairs were averaged for the refinement ; 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8054(5) _cell_length_b 10.1991(9) _cell_length_c 14.3886(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1145.45(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6885 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 29.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9936 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68840 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Thin slice, \w-scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 8116 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.43 _reflns_number_total 1870 _reflns_number_gt 1712 _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^)+(0.0635P)^2^+0.1206P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3.0(12) _refine_ls_number_reflns 1870 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 -0.37233(18) 0.52809(15) 0.52996(11) 0.0453(4) Uani 1 1 d . . . O2 O -0.09727(17) 0.51286(15) 0.49968(10) 0.0445(3) Uani 1 1 d . . . O3 O -0.20444(16) 0.67257(14) 0.59663(11) 0.0420(3) Uani 1 1 d . . . O4 O 0.25702(16) 0.67946(13) 0.61772(9) 0.0363(3) Uani 1 1 d . A . O5 O 0.3243(2) 0.53761(15) 0.73162(13) 0.0533(4) Uani 1 1 d . . . C1 C -0.2305(2) 0.56980(17) 0.54177(13) 0.0349(4) Uani 1 1 d . A . C2 C -0.0361(2) 0.73272(18) 0.60241(18) 0.0458(5) Uani 0.65 1 d P A 1 H2 H -0.0133 0.7929 0.5490 0.055 Uiso 0.65 1 calc PR A 1 C3 C -0.0328(4) 0.8088(3) 0.7008(3) 0.0370(6) Uani 0.65 1 d P A 1 H3A H -0.1492 0.8403 0.7166 0.044 Uiso 0.65 1 calc PR A 1 H3B H 0.0060 0.7488 0.7506 0.044 Uiso 0.65 1 calc PR A 1 C4 C 0.0882(4) 0.9228(3) 0.6925(2) 0.0413(6) Uani 0.65 1 d P A 1 H4 H 0.0490 0.9947 0.6563 0.050 Uiso 0.65 1 calc PR A 1 C5 C 0.2430(5) 0.9355(3) 0.7297(2) 0.0426(7) Uani 0.65 1 d P A 1 H5 H 0.3013 1.0151 0.7163 0.051 Uiso 0.65 1 calc PR A 1 C6 C 0.3372(5) 0.8401(4) 0.7898(3) 0.0424(8) Uani 0.65 1 d P A 1 H6A H 0.2537 0.7861 0.8247 0.051 Uiso 0.65 1 calc PR A 1 H6B H 0.4077 0.8887 0.8355 0.051 Uiso 0.65 1 calc PR A 1 C7 C 0.4519(2) 0.7514(2) 0.73231(16) 0.0467(5) Uani 0.65 1 d P A 1 H7A H 0.5029 0.8013 0.6802 0.056 Uiso 0.65 1 calc PR A 1 H7B H 0.5459 0.7164 0.7713 0.056 Uiso 0.65 1 calc PR A 1 C2' C -0.0361(2) 0.73272(18) 0.60241(18) 0.0458(5) Uani 0.35 1 d P A 2 H2' H -0.0192 0.7665 0.5378 0.055 Uiso 0.35 1 calc PR A 2 C3' C -0.0401(8) 0.8508(6) 0.6557(5) 0.0399(12) Uani 0.35 1 d P A 2 H3'1 H -0.1551 0.8916 0.6533 0.048 Uiso 0.35 1 calc PR A 2 H3'2 H 0.0453 0.9145 0.6322 0.048 Uiso 0.35 1 calc PR A 2 C4' C 0.0023(8) 0.8095(6) 0.7519(5) 0.0384(11) Uani 0.35 1 d P A 2 H4' H -0.0859 0.7688 0.7871 0.046 Uiso 0.35 1 calc PR A 2 C5' C 0.1557(7) 0.8249(6) 0.7933(4) 0.0399(11) Uani 0.35 1 d P A 2 H5' H 0.1623 0.8002 0.8569 0.048 Uiso 0.35 1 calc PR A 2 C6' C 0.3154(9) 0.8760(8) 0.7509(6) 0.0429(15) Uani 0.35 1 d P A 2 H6'1 H 0.3688 0.9411 0.7929 0.051 Uiso 0.35 1 calc PR A 2 H6'2 H 0.2887 0.9200 0.6914 0.051 Uiso 0.35 1 calc PR A 2 C7' C 0.4519(2) 0.7514(2) 0.73231(16) 0.0467(5) Uani 0.35 1 d P A 2 H7'1 H 0.5406 0.7767 0.6865 0.056 Uiso 0.35 1 calc PR A 2 H7'2 H 0.5091 0.7255 0.7909 0.056 Uiso 0.35 1 calc PR A 2 C8 C 0.3445(2) 0.64092(19) 0.69555(15) 0.0393(4) Uani 1 1 d . . . C9 C 0.09077(19) 0.62228(17) 0.60686(12) 0.0312(3) Uani 1 1 d . . . H9 H 0.0645 0.5644 0.6611 0.037 Uiso 1 1 calc R A 1 C10 C 0.0809(2) 0.54410(17) 0.51775(13) 0.0337(3) Uani 1 1 d . A . H10 H 0.1254 0.5993 0.4656 0.040 Uiso 1 1 calc R . . C11 C 0.1824(2) 0.42032(19) 0.52179(15) 0.0424(4) Uani 1 1 d . . . H11 H 0.3034 0.4281 0.5264 0.051 Uiso 1 1 calc R A . C12 C 0.1179(3) 0.3015(2) 0.5195(2) 0.0651(7) Uani 1 1 d . A . H12A H -0.0025 0.2895 0.5150 0.078 Uiso 1 1 calc R . . H12B H 0.1916 0.2275 0.5225 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0301(6) 0.0465(7) 0.0592(8) 0.0087(7) -0.0106(6) -0.0075(5) O2 0.0322(6) 0.0461(7) 0.0552(8) -0.0146(6) -0.0108(6) 0.0036(5) O3 0.0228(6) 0.0423(7) 0.0609(8) -0.0088(7) 0.0049(6) -0.0019(5) O4 0.0219(5) 0.0415(6) 0.0456(7) -0.0106(5) 0.0056(5) -0.0067(5) O5 0.0349(7) 0.0475(8) 0.0776(11) 0.0021(8) -0.0124(7) 0.0017(6) C1 0.0291(7) 0.0330(8) 0.0425(9) 0.0068(7) -0.0043(7) -0.0015(6) C2 0.0231(7) 0.0326(8) 0.0818(14) -0.0170(9) 0.0069(9) -0.0019(7) C3 0.0297(14) 0.0385(16) 0.043(2) -0.0114(16) 0.0073(15) -0.0015(12) C4 0.0444(15) 0.0296(11) 0.0500(15) -0.0119(11) 0.0081(13) -0.0026(11) C5 0.0470(17) 0.0296(13) 0.0512(16) -0.0117(12) 0.0085(15) -0.0076(13) C6 0.0401(17) 0.048(2) 0.0394(19) -0.0111(15) 0.0035(15) -0.0090(15) C7 0.0275(9) 0.0608(12) 0.0517(10) -0.0144(10) 0.0021(8) -0.0117(9) C2' 0.0231(7) 0.0326(8) 0.0818(14) -0.0170(9) 0.0069(9) -0.0019(7) C3' 0.036(3) 0.040(3) 0.044(3) -0.006(3) -0.001(3) 0.007(2) C4' 0.030(2) 0.046(3) 0.039(3) -0.004(3) 0.004(2) 0.005(2) C5' 0.031(2) 0.049(3) 0.040(3) -0.003(2) 0.007(2) -0.007(2) C6' 0.035(3) 0.044(4) 0.050(4) -0.009(3) 0.006(3) -0.010(3) C7' 0.0275(9) 0.0608(12) 0.0517(10) -0.0144(10) 0.0021(8) -0.0117(9) C8 0.0199(7) 0.0442(9) 0.0537(10) -0.0118(8) 0.0029(7) -0.0009(6) C9 0.0197(6) 0.0330(7) 0.0407(8) -0.0075(6) 0.0036(6) -0.0025(6) C10 0.0291(7) 0.0329(7) 0.0391(8) -0.0045(6) 0.0022(6) -0.0002(6) C11 0.0307(8) 0.0400(9) 0.0565(11) -0.0155(8) 0.0007(8) 0.0061(7) C12 0.0450(11) 0.0370(10) 0.113(2) -0.0218(12) -0.0035(14) 0.0064(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.198(2) . ? O2 C1 1.336(2) . ? O2 C10 1.450(2) . ? O3 C1 1.328(2) . ? O3 C2 1.452(2) . ? O4 C8 1.369(2) . ? O4 C9 1.4313(19) . ? O5 C8 1.185(3) . ? C2 C9 1.501(2) . ? C2 C3 1.614(4) . ? C2 H2 1.0000 . ? C3 C4 1.503(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.328(5) . ? C4 H4 0.9500 . ? C5 C6 1.495(5) . ? C5 H5 0.9500 . ? C6 C7 1.519(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.500(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C3' C4' 1.483(10) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.347(9) . ? C4' H4' 0.9500 . ? C5' C6' 1.482(9) . ? C5' H5' 0.9500 . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C9 C10 1.512(2) . ? C9 H9 1.0000 . ? C10 C11 1.491(2) . ? C10 H10 1.0000 . ? C11 C12 1.312(3) . ? C11 H11 0.9500 . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C10 124.72(14) . . ? C1 O3 C2 120.40(14) . . ? C8 O4 C9 115.11(14) . . ? O1 C1 O3 120.41(17) . . ? O1 C1 O2 120.03(17) . . ? O3 C1 O2 119.56(15) . . ? O3 C2 C9 106.40(14) . . ? O3 C2 C3 105.51(18) . . ? C9 C2 C3 108.2(2) . . ? O3 C2 H2 112.1 . . ? C9 C2 H2 112.1 . . ? C3 C2 H2 112.1 . . ? C4 C3 C2 108.2(3) . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C5 C4 C3 128.0(4) . . ? C5 C4 H4 116.0 . . ? C3 C4 H4 116.0 . . ? C4 C5 C6 128.1(3) . . ? C4 C5 H5 115.9 . . ? C6 C5 H5 115.9 . . ? C5 C6 C7 111.2(3) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 108.1(2) . . ? C8 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C4' C3' H3'1 110.8 . . ? C4' C3' H3'2 110.8 . . ? H3'1 C3' H3'2 108.9 . . ? C5' C4' C3' 125.3(6) . . ? C5' C4' H4' 117.3 . . ? C3' C4' H4' 117.3 . . ? C4' C5' C6' 127.3(6) . . ? C4' C5' H5' 116.3 . . ? C6' C5' H5' 116.3 . . ? C5' C6' H6'1 109.8 . . ? C5' C6' H6'2 109.8 . . ? H6'1 C6' H6'2 108.2 . . ? O5 C8 O4 123.17(17) . . ? O5 C8 C7 126.0(2) . . ? O4 C8 C7 110.57(17) . . ? O4 C9 C2 107.28(13) . . ? O4 C9 C10 110.70(13) . . ? C2 C9 C10 109.03(16) . . ? O4 C9 H9 109.9 . . ? C2 C9 H9 109.9 . . ? C10 C9 H9 109.9 . . ? O2 C10 C11 109.27(14) . . ? O2 C10 C9 108.46(13) . . ? C11 C10 C9 112.73(15) . . ? O2 C10 H10 108.8 . . ? C11 C10 H10 108.8 . . ? C9 C10 H10 108.8 . . ? C12 C11 C10 125.24(18) . . ? C12 C11 H11 117.4 . . ? C10 C11 H11 117.4 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 O3 C1 O1 -172.69(19) . . . . ? C2 O3 C1 O2 7.3(3) . . . . ? C10 O2 C1 O1 -171.88(18) . . . . ? C10 O2 C1 O3 8.1(3) . . . . ? C1 O3 C2 C9 -42.6(3) . . . . ? C1 O3 C2 C3 -157.5(2) . . . . ? O3 C2 C3 C4 -151.9(3) . . . . ? C9 C2 C3 C4 94.6(3) . . . . ? C2 C3 C4 C5 -107.2(4) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C4 C5 C6 C7 92.8(4) . . . . ? C5 C6 C7 C8 -83.3(3) . . . . ? C3' C4' C5' C6' -4.9(11) . . . . ? C9 O4 C8 O5 28.3(2) . . . . ? C9 O4 C8 C7 -145.88(15) . . . . ? C6 C7 C8 O5 -92.3(3) . . . . ? C6 C7 C8 O4 81.7(3) . . . . ? C8 O4 C9 C2 121.61(18) . . . . ? C8 O4 C9 C10 -119.54(16) . . . . ? O3 C2 C9 O4 -176.90(16) . . . . ? C3 C2 C9 O4 -63.9(2) . . . . ? O3 C2 C9 C10 63.2(2) . . . . ? C3 C2 C9 C10 176.15(18) . . . . ? C1 O2 C10 C11 137.86(18) . . . . ? C1 O2 C10 C9 14.6(2) . . . . ? O4 C9 C10 O2 -167.60(14) . . . . ? C2 C9 C10 O2 -49.81(19) . . . . ? O4 C9 C10 C11 71.26(19) . . . . ? C2 C9 C10 C11 -170.95(15) . . . . ? O2 C10 C11 C12 -6.8(3) . . . . ? C9 C10 C11 C12 113.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 29.43 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.273 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.033 data_ah9904 _database_code_depnum_ccdc_archive 'CCDC 655148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H44 O5 Si' _chemical_formula_sum 'C26 H44 O5 Si' _chemical_formula_weight 464.70 _chemical_absolute_configuration ; Flack parameter -0.17(19) ; 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.040(3) _cell_length_b 16.929(3) _cell_length_c 19.604(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2668.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4732 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.07 _reflns_number_total 4732 _reflns_number_gt 3944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.17(19) _refine_ls_number_reflns 4732 _refine_ls_number_parameters 326 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.246 _refine_ls_restrained_S_all 1.237 _refine_ls_shift/su_max 0.004 _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 Si1 Si 0.00565(12) 0.06672(5) -0.39713(5) 0.0399(3) Uani 1 1 d . . . O1 O -0.2132(2) -0.08596(11) -0.56022(11) 0.0291(5) Uani 1 1 d . . . O2 O -0.0651(2) -0.25120(12) -0.66174(11) 0.0341(5) Uani 1 1 d . A . O3 O 0.5098(3) -0.41043(15) -0.82738(14) 0.0515(7) Uani 1 1 d . A . O4 O 0.1323(3) -0.06287(15) -0.56180(15) 0.0531(7) Uani 1 1 d . A . H100 H 0.0691 -0.0272 -0.5472 0.080 Uiso 1 1 calc R . . O5 O -0.0610(3) 0.00126(12) -0.45419(12) 0.0386(5) Uani 1 1 d . A . C1 C -0.1411(4) -0.07287(17) -0.43960(17) 0.0341(7) Uani 1 1 d . . . H1A H -0.1897 -0.0717 -0.3932 0.041 Uiso 1 1 calc R A . H1B H -0.0589 -0.1163 -0.4416 0.041 Uiso 1 1 calc R . . C2 C -0.2761(4) -0.08639(16) -0.49172(16) 0.0299(7) Uani 1 1 d . A . H2 H -0.3527 -0.0400 -0.4882 0.036 Uiso 1 1 calc R . . C3 C -0.3811(4) -0.15905(18) -0.47551(17) 0.0336(7) Uani 1 1 d . . . H3A H -0.3094 -0.2066 -0.4739 0.040 Uiso 1 1 calc R A . H3B H -0.4346 -0.1527 -0.4303 0.040 Uiso 1 1 calc R . . C4 C -0.5121(4) -0.16896(18) -0.52959(17) 0.0377(8) Uani 1 1 d . A . H4 H -0.6181 -0.1459 -0.5219 0.045 Uiso 1 1 calc R . . C5 C -0.4886(4) -0.20789(19) -0.58723(18) 0.0401(8) Uani 1 1 d . . . H5 H -0.5763 -0.2077 -0.6197 0.048 Uiso 1 1 calc R A . C6 C -0.3327(4) -0.25252(18) -0.60517(18) 0.0359(7) Uani 1 1 d . A . H6A H -0.3612 -0.2940 -0.6388 0.043 Uiso 1 1 calc R . . H6B H -0.2908 -0.2792 -0.5636 0.043 Uiso 1 1 calc R . . C7 C -0.1936(4) -0.20133(18) -0.63462(18) 0.0324(7) Uani 1 1 d . . . H7 H -0.2394 -0.1673 -0.6718 0.039 Uiso 1 1 calc R A . C8 C -0.1050(3) -0.14935(17) -0.58166(17) 0.0299(7) Uani 1 1 d . A . H8 H -0.0720 -0.1820 -0.5414 0.036 Uiso 1 1 calc R . . C9 C 0.0476(4) -0.1083(2) -0.6114(2) 0.0432(9) Uani 1 1 d . . . H9A H 0.1243 -0.1485 -0.6302 0.052 Uiso 1 1 calc R A . H9B H 0.0126 -0.0734 -0.6493 0.052 Uiso 1 1 calc R . . C10 C -0.0941(4) -0.2798(2) -0.72922(18) 0.0414(8) Uani 1 1 d . . . H10A H -0.1267 -0.2356 -0.7595 0.050 Uiso 1 1 calc R A . H10B H -0.1852 -0.3191 -0.7289 0.050 Uiso 1 1 calc R . . C11 C 0.0639(4) -0.31727(17) -0.75482(17) 0.0347(7) Uani 1 1 d . A . C12 C 0.0611(4) -0.37294(18) -0.80643(18) 0.0390(8) Uani 1 1 d . . . H12 H -0.0430 -0.3892 -0.8245 0.047 Uiso 1 1 calc R A . C13 C 0.2061(4) -0.40586(19) -0.83271(19) 0.0413(8) Uani 1 1 d . A . H13 H 0.2007 -0.4439 -0.8683 0.050 Uiso 1 1 calc R . . C14 C 0.3578(4) -0.38281(19) -0.80663(19) 0.0385(8) Uani 1 1 d . . . C15 C 0.3633(4) -0.3273(2) -0.7544(2) 0.0476(9) Uani 1 1 d . A . H15 H 0.4672 -0.3115 -0.7359 0.057 Uiso 1 1 calc R . . C16 C 0.2181(4) -0.2953(2) -0.7296(2) 0.0459(9) Uani 1 1 d . . . H16 H 0.2237 -0.2570 -0.6942 0.055 Uiso 1 1 calc R A . C17 C 0.5119(5) -0.4649(3) -0.8831(2) 0.0628(12) Uani 1 1 d . . . H17A H 0.4606 -0.4403 -0.9231 0.094 Uiso 1 1 calc R A . H17B H 0.4495 -0.5125 -0.8706 0.094 Uiso 1 1 calc R . . H17C H 0.6271 -0.4792 -0.8937 0.094 Uiso 1 1 calc R . . C18 C 0.1468(14) 0.1330(7) -0.4481(6) 0.040(3) Uani 0.50 1 d PU A 1 H18 H 0.2567 0.1059 -0.4529 0.047 Uiso 0.50 1 calc PR A 1 C19 C 0.176(3) 0.2123(9) -0.4145(9) 0.095(7) Uani 0.50 1 d PU A 1 H19A H 0.0702 0.2402 -0.4098 0.142 Uiso 0.50 1 calc PR A 1 H19B H 0.2522 0.2437 -0.4428 0.142 Uiso 0.50 1 calc PR A 1 H19C H 0.2257 0.2042 -0.3694 0.142 Uiso 0.50 1 calc PR A 1 C20 C 0.0746(12) 0.1473(5) -0.5220(4) 0.0492(18) Uani 0.50 1 d PU A 1 H20A H 0.1497 0.1821 -0.5475 0.074 Uiso 0.50 1 calc PR A 1 H20B H -0.0352 0.1722 -0.5186 0.074 Uiso 0.50 1 calc PR A 1 H20C H 0.0645 0.0967 -0.5459 0.074 Uiso 0.50 1 calc PR A 1 C18' C 0.0807(17) 0.1508(7) -0.4575(8) 0.053(3) Uani 0.50 1 d PU A 2 H18' H -0.0135 0.1575 -0.4904 0.064 Uiso 0.50 1 calc PR A 2 C19' C 0.2232(17) 0.1332(6) -0.5011(7) 0.090(4) Uani 0.50 1 d PU A 2 H19D H 0.3233 0.1279 -0.4730 0.135 Uiso 0.50 1 calc PR A 2 H19E H 0.2387 0.1762 -0.5340 0.135 Uiso 0.50 1 calc PR A 2 H19F H 0.2032 0.0837 -0.5257 0.135 Uiso 0.50 1 calc PR A 2 C20' C 0.096(2) 0.2321(11) -0.4233(10) 0.089(6) Uani 0.50 1 d PU A 2 H20D H 0.1134 0.2727 -0.4582 0.133 Uiso 0.50 1 calc PR A 2 H20E H 0.1908 0.2318 -0.3918 0.133 Uiso 0.50 1 calc PR A 2 H20F H -0.0061 0.2437 -0.3979 0.133 Uiso 0.50 1 calc PR A 2 C21 C 0.1473(5) 0.0134(2) -0.3352(2) 0.0536(10) Uani 1 1 d U A . H21 H 0.0790 -0.0298 -0.3145 0.064 Uiso 1 1 calc R . . C22 C 0.2073(7) 0.0650(4) -0.2757(3) 0.0840(15) Uani 1 1 d U . . H22A H 0.2677 0.1108 -0.2936 0.126 Uiso 1 1 calc R A . H22B H 0.2813 0.0341 -0.2463 0.126 Uiso 1 1 calc R . . H22C H 0.1112 0.0831 -0.2492 0.126 Uiso 1 1 calc R . . C23 C 0.2934(5) -0.0273(3) -0.3707(3) 0.0674(13) Uani 1 1 d U . . H23A H 0.3525 -0.0608 -0.3379 0.101 Uiso 1 1 calc R A . H23B H 0.3697 0.0127 -0.3888 0.101 Uiso 1 1 calc R . . H23C H 0.2517 -0.0600 -0.4083 0.101 Uiso 1 1 calc R . . C24 C -0.1777(5) 0.1117(2) -0.3513(2) 0.0508(9) Uani 1 1 d U A . H24 H -0.1345 0.1582 -0.3254 0.061 Uiso 1 1 calc R . . C25 C -0.3100(7) 0.1436(3) -0.4018(3) 0.0821(15) Uani 1 1 d U . . H25A H -0.4013 0.1679 -0.3762 0.123 Uiso 1 1 calc R A . H25B H -0.3534 0.0999 -0.4293 0.123 Uiso 1 1 calc R . . H25C H -0.2590 0.1831 -0.4317 0.123 Uiso 1 1 calc R . . C26 C -0.2600(5) 0.0569(2) -0.2990(2) 0.0573(10) Uani 1 1 d U . . H26A H -0.3088 0.0114 -0.3226 0.086 Uiso 1 1 calc R A . H26B H -0.3475 0.0858 -0.2747 0.086 Uiso 1 1 calc R . . H26C H -0.1763 0.0385 -0.2663 0.086 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 Si1 0.0511(5) 0.0344(5) 0.0343(5) -0.0057(4) 0.0033(5) -0.0127(4) O1 0.0318(10) 0.0272(10) 0.0285(12) 0.0020(9) 0.0033(9) 0.0029(8) O2 0.0366(11) 0.0393(11) 0.0263(12) -0.0070(10) -0.0024(9) 0.0077(9) O3 0.0390(12) 0.0607(14) 0.0550(17) -0.0236(13) 0.0035(12) 0.0055(11) O4 0.0356(11) 0.0514(14) 0.072(2) -0.0255(14) 0.0125(12) -0.0129(11) O5 0.0479(12) 0.0327(11) 0.0352(13) -0.0050(10) 0.0051(10) -0.0121(10) C1 0.0423(16) 0.0301(15) 0.0297(19) -0.0019(13) 0.0007(14) -0.0051(14) C2 0.0302(14) 0.0280(14) 0.0316(18) -0.0012(13) 0.0051(13) 0.0013(13) C3 0.0360(16) 0.0355(15) 0.0293(18) -0.0003(14) 0.0062(14) -0.0043(14) C4 0.0263(15) 0.0398(16) 0.047(2) 0.0020(15) 0.0014(15) -0.0073(14) C5 0.0302(15) 0.0469(17) 0.043(2) 0.0008(15) -0.0055(15) -0.0080(14) C6 0.0390(17) 0.0360(15) 0.0327(19) -0.0044(15) -0.0040(14) -0.0042(13) C7 0.0321(15) 0.0333(15) 0.0318(19) -0.0035(13) -0.0016(13) 0.0059(13) C8 0.0279(14) 0.0296(14) 0.0323(18) -0.0026(13) 0.0009(13) 0.0045(12) C9 0.0361(16) 0.0448(18) 0.049(2) -0.0096(17) 0.0129(15) -0.0038(14) C10 0.0448(19) 0.0490(19) 0.030(2) -0.0069(16) -0.0065(15) 0.0096(16) C11 0.0398(16) 0.0363(16) 0.0282(19) -0.0008(14) -0.0011(14) 0.0029(13) C12 0.0379(16) 0.0401(16) 0.039(2) -0.0090(15) -0.0032(15) -0.0023(14) C13 0.0481(18) 0.0366(16) 0.039(2) -0.0142(15) 0.0014(16) -0.0023(15) C14 0.0396(17) 0.0387(16) 0.037(2) -0.0040(15) 0.0008(15) 0.0028(14) C15 0.0392(18) 0.058(2) 0.046(2) -0.0194(19) -0.0085(17) 0.0010(16) C16 0.050(2) 0.0508(19) 0.037(2) -0.0219(16) -0.0069(17) 0.0053(17) C17 0.052(2) 0.073(3) 0.063(3) -0.034(2) 0.008(2) 0.004(2) C18 0.044(6) 0.038(6) 0.037(5) 0.014(4) -0.017(5) -0.011(4) C19 0.183(18) 0.053(9) 0.048(7) 0.013(6) -0.032(11) -0.076(11) C20 0.064(5) 0.048(4) 0.036(5) 0.009(3) -0.009(4) -0.016(4) C18' 0.060(8) 0.042(6) 0.058(9) -0.005(5) 0.004(6) -0.013(6) C19' 0.125(10) 0.056(5) 0.090(8) -0.016(6) 0.055(8) -0.025(6) C20' 0.142(14) 0.053(8) 0.071(12) -0.018(8) 0.045(11) -0.026(8) C21 0.048(2) 0.058(2) 0.056(3) -0.008(2) -0.0074(19) -0.0146(17) C22 0.079(3) 0.106(4) 0.067(3) -0.021(3) -0.024(3) -0.013(3) C23 0.051(2) 0.061(2) 0.090(4) 0.000(2) -0.008(2) -0.0008(19) C24 0.070(2) 0.0394(18) 0.043(2) -0.0068(16) 0.0029(19) 0.0036(17) C25 0.097(4) 0.080(3) 0.070(3) 0.007(3) 0.000(3) 0.039(3) C26 0.064(2) 0.050(2) 0.057(3) -0.002(2) 0.018(2) 0.001(2) _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 Si1 O5 1.663(2) . ? Si1 C18 1.883(12) . ? Si1 C24 1.887(4) . ? Si1 C21 1.894(4) . ? Si1 C18' 1.947(14) . ? O1 C2 1.435(4) . ? O1 C8 1.444(3) . ? O2 C10 1.427(4) . ? O2 C7 1.436(4) . ? O3 C14 1.370(4) . ? O3 C17 1.429(4) . ? O4 C9 1.414(4) . ? O4 H100 0.8400 . ? O5 C1 1.439(4) . ? C1 C2 1.508(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.526(4) . ? C2 H2 1.0000 . ? C3 C4 1.504(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.322(5) . ? C4 H4 0.9500 . ? C5 C6 1.505(5) . ? C5 H5 0.9500 . ? C6 C7 1.528(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.536(4) . ? C7 H7 1.0000 . ? C8 C9 1.526(4) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.506(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.383(4) . ? C11 C16 1.385(5) . ? C12 C13 1.391(5) . ? C12 H12 0.9500 . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 C15 1.390(5) . ? C15 C16 1.376(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.51(2) . ? C18 C20 1.581(13) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C18' C19' 1.460(17) . ? C18' C20' 1.54(2) . ? C18' H18' 1.0000 . ? C19' H19D 0.9800 . ? C19' H19E 0.9800 . ? C19' H19F 0.9800 . ? C20' H20D 0.9800 . ? C20' H20E 0.9800 . ? C20' H20F 0.9800 . ? C21 C23 1.530(6) . ? C21 C22 1.536(6) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.531(6) . ? C24 C25 1.550(6) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 Si1 C18 103.5(4) . . ? O5 Si1 C24 109.71(15) . . ? C18 Si1 C24 118.9(4) . . ? O5 Si1 C21 107.87(15) . . ? C18 Si1 C21 105.2(3) . . ? C24 Si1 C21 110.91(19) . . ? O5 Si1 C18' 100.2(4) . . ? C18 Si1 C18' 19.1(3) . . ? C24 Si1 C18' 103.7(4) . . ? C21 Si1 C18' 123.5(4) . . ? C2 O1 C8 118.7(2) . . ? C10 O2 C7 115.1(2) . . ? C14 O3 C17 117.2(3) . . ? C9 O4 H100 109.5 . . ? C1 O5 Si1 126.3(2) . . ? O5 C1 C2 108.7(3) . . ? O5 C1 H1A 110.0 . . ? C2 C1 H1A 110.0 . . ? O5 C1 H1B 110.0 . . ? C2 C1 H1B 110.0 . . ? H1A C1 H1B 108.3 . . ? O1 C2 C1 112.3(2) . . ? O1 C2 C3 113.2(2) . . ? C1 C2 C3 112.3(3) . . ? O1 C2 H2 106.1 . . ? C1 C2 H2 106.1 . . ? C3 C2 H2 106.1 . . ? C4 C3 C2 109.3(3) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 123.9(3) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 118.0 . . ? C4 C5 C6 124.7(3) . . ? C4 C5 H5 117.6 . . ? C6 C5 H5 117.6 . . ? C5 C6 C7 114.4(3) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O2 C7 C6 109.5(2) . . ? O2 C7 C8 104.6(2) . . ? C6 C7 C8 114.1(3) . . ? O2 C7 H7 109.5 . . ? C6 C7 H7 109.5 . . ? C8 C7 H7 109.5 . . ? O1 C8 C9 104.9(2) . . ? O1 C8 C7 110.0(2) . . ? C9 C8 C7 112.1(3) . . ? O1 C8 H8 109.9 . . ? C9 C8 H8 109.9 . . ? C7 C8 H8 109.9 . . ? O4 C9 C8 111.9(3) . . ? O4 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? O4 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O2 C10 C11 108.3(3) . . ? O2 C10 H10A 110.0 . . ? C11 C10 H10A 110.0 . . ? O2 C10 H10B 110.0 . . ? C11 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? C12 C11 C16 117.3(3) . . ? C12 C11 C10 121.2(3) . . ? C16 C11 C10 121.5(3) . . ? C11 C12 C13 122.0(3) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? O3 C14 C13 125.6(3) . . ? O3 C14 C15 114.9(3) . . ? C13 C14 C15 119.5(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.8(3) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 108.6(9) . . ? C19 C18 Si1 113.1(11) . . ? C20 C18 Si1 110.9(7) . . ? C19 C18 H18 108.0 . . ? C20 C18 H18 108.0 . . ? Si1 C18 H18 108.0 . . ? C19' C18' C20' 112.0(11) . . ? C19' C18' Si1 116.7(9) . . ? C20' C18' Si1 114.5(11) . . ? C19' C18' H18' 103.9 . . ? C20' C18' H18' 103.9 . . ? Si1 C18' H18' 103.9 . . ? C18' C19' H19D 109.5 . . ? C18' C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? C18' C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? C18' C20' H20D 109.5 . . ? C18' C20' H20E 109.5 . . ? H20D C20' H20E 109.5 . . ? C18' C20' H20F 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 109.5 . . ? C23 C21 C22 111.2(4) . . ? C23 C21 Si1 112.7(3) . . ? C22 C21 Si1 113.8(3) . . ? C23 C21 H21 106.2 . . ? C22 C21 H21 106.2 . . ? Si1 C21 H21 106.2 . . ? 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 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C25 110.0(4) . . ? C26 C24 Si1 114.3(3) . . ? C25 C24 Si1 111.9(3) . . ? C26 C24 H24 106.7 . . ? C25 C24 H24 106.7 . . ? Si1 C24 H24 106.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C18 Si1 O5 C1 164.7(4) . . . . ? C24 Si1 O5 C1 -67.3(3) . . . . ? C21 Si1 O5 C1 53.6(3) . . . . ? C18' Si1 O5 C1 -176.0(5) . . . . ? Si1 O5 C1 C2 141.7(2) . . . . ? C8 O1 C2 C1 67.8(3) . . . . ? C8 O1 C2 C3 -60.7(3) . . . . ? O5 C1 C2 O1 57.6(3) . . . . ? O5 C1 C2 C3 -173.4(2) . . . . ? O1 C2 C3 C4 -51.2(3) . . . . ? C1 C2 C3 C4 -179.8(3) . . . . ? C2 C3 C4 C5 87.1(4) . . . . ? C3 C4 C5 C6 4.4(5) . . . . ? C4 C5 C6 C7 -83.1(4) . . . . ? C10 O2 C7 C6 83.1(3) . . . . ? C10 O2 C7 C8 -154.2(3) . . . . ? C5 C6 C7 O2 -169.0(3) . . . . ? C5 C6 C7 C8 74.1(4) . . . . ? C2 O1 C8 C9 -127.8(3) . . . . ? C2 O1 C8 C7 111.4(3) . . . . ? O2 C7 C8 O1 168.7(2) . . . . ? C6 C7 C8 O1 -71.7(3) . . . . ? O2 C7 C8 C9 52.4(3) . . . . ? C6 C7 C8 C9 172.0(2) . . . . ? O1 C8 C9 O4 62.9(3) . . . . ? C7 C8 C9 O4 -177.8(3) . . . . ? C7 O2 C10 C11 169.3(2) . . . . ? O2 C10 C11 C12 157.2(3) . . . . ? O2 C10 C11 C16 -25.4(4) . . . . ? C16 C11 C12 C13 -0.2(5) . . . . ? C10 C11 C12 C13 177.3(3) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C17 O3 C14 C13 3.3(5) . . . . ? C17 O3 C14 C15 -177.2(3) . . . . ? C12 C13 C14 O3 179.7(4) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? O3 C14 C15 C16 179.8(3) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? C14 C15 C16 C11 0.5(6) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C10 C11 C16 C15 -177.7(4) . . . . ? O5 Si1 C18 C19 160.3(9) . . . . ? C24 Si1 C18 C19 38.3(10) . . . . ? C21 Si1 C18 C19 -86.6(9) . . . . ? C18' Si1 C18 C19 78(2) . . . . ? O5 Si1 C18 C20 38.0(8) . . . . ? C24 Si1 C18 C20 -84.0(8) . . . . ? C21 Si1 C18 C20 151.0(7) . . . . ? C18' Si1 C18 C20 -44.2(18) . . . . ? O5 Si1 C18' C19' -66.1(11) . . . . ? C18 Si1 C18' C19' 35.8(18) . . . . ? C24 Si1 C18' C19' -179.4(10) . . . . ? C21 Si1 C18' C19' 53.5(12) . . . . ? O5 Si1 C18' C20' 160.3(11) . . . . ? C18 Si1 C18' C20' -98(3) . . . . ? C24 Si1 C18' C20' 46.9(12) . . . . ? C21 Si1 C18' C20' -80.2(12) . . . . ? O5 Si1 C21 C23 57.1(3) . . . . ? C18 Si1 C21 C23 -52.9(5) . . . . ? C24 Si1 C21 C23 177.3(3) . . . . ? C18' Si1 C21 C23 -58.8(6) . . . . ? O5 Si1 C21 C22 -175.1(3) . . . . ? C18 Si1 C21 C22 74.8(5) . . . . ? C24 Si1 C21 C22 -55.0(4) . . . . ? C18' Si1 C21 C22 68.9(6) . . . . ? O5 Si1 C24 C26 74.3(3) . . . . ? C18 Si1 C24 C26 -166.8(4) . . . . ? C21 Si1 C24 C26 -44.7(3) . . . . ? C18' Si1 C24 C26 -179.3(5) . . . . ? O5 Si1 C24 C25 -51.5(3) . . . . ? C18 Si1 C24 C25 67.3(5) . . . . ? C21 Si1 C24 C25 -170.6(3) . . . . ? C18' Si1 C24 C25 54.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.542 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.199 # Attachment 'dilactone 63 cif.cif' data_ah9911 _database_code_depnum_ccdc_archive 'CCDC 655149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 O4' _chemical_formula_sum 'C13 H16 O4' _chemical_formula_weight 236.26 _chemical_absolute_configuration ; 1147 Friedel pairs were averaged for the refinement ; 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.720(4) _cell_length_b 6.415(3) _cell_length_c 12.126(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.616(11) _cell_angle_gamma 90.00 _cell_volume 596.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3734 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 29.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9904 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68910 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 9.8' _diffrn_radiation_monochromator 'Si 111' _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'thin slice / omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 4168 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 29.63 _reflns_number_total 1767 _reflns_number_gt 1584 _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^)+(0.0795P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(12) _refine_ls_number_reflns 1767 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.1399(2) 1.4252(3) 0.73296(13) 0.0322(3) Uani 1 1 d . . . O2 O 0.41870(19) 1.3847(2) 0.80408(11) 0.0272(3) Uani 1 1 d . . . O3 O 0.60150(17) 0.9185(2) 0.70091(10) 0.0231(3) Uani 1 1 d . . . O4 O 0.8442(2) 0.9142(4) 0.82073(12) 0.0459(5) Uani 1 1 d . . . C1 C 0.2441(3) 1.3938(3) 0.81142(16) 0.0265(4) Uani 1 1 d . . . C2 C 0.2064(3) 1.3516(4) 0.92799(17) 0.0368(5) Uani 1 1 d . . . H2A H 0.0790 1.3383 0.9300 0.044 Uiso 1 1 calc R . . H2B H 0.2491 1.4687 0.9769 0.044 Uiso 1 1 calc R . . C3 C 0.2986(3) 1.1473(4) 0.96935(17) 0.0345(5) Uani 1 1 d . . . H3A H 0.4259 1.1715 0.9830 0.041 Uiso 1 1 calc R . . H3B H 0.2574 1.1052 1.0404 0.041 Uiso 1 1 calc R . . C4 C 0.2624(3) 0.9748(4) 0.88593(18) 0.0305(4) Uani 1 1 d . . . H4 H 0.1655 0.8873 0.8942 0.037 Uiso 1 1 calc R . . C5 C 0.3530(3) 0.9327(3) 0.80145(16) 0.0256(4) Uani 1 1 d . . . H5 H 0.3122 0.8212 0.7538 0.031 Uiso 1 1 calc R . . C6 C 0.5127(2) 1.0446(3) 0.77475(16) 0.0218(4) Uani 1 1 d . . . H6 H 0.5918 1.0685 0.8449 0.026 Uiso 1 1 calc R . . C7 C 0.7737(3) 0.8903(4) 0.72869(16) 0.0269(4) Uani 1 1 d . . . C8 C 0.8644(3) 0.8416(3) 0.62879(17) 0.0286(4) Uani 1 1 d . . . H8A H 0.7872 0.7587 0.5746 0.034 Uiso 1 1 calc R . . H8B H 0.9719 0.7604 0.6508 0.034 Uiso 1 1 calc R . . C9 C 0.9100(3) 1.0534(3) 0.57678(18) 0.0281(4) Uani 1 1 d . . . H9A H 0.9614 1.1469 0.6368 0.034 Uiso 1 1 calc R . . H9B H 0.9995 1.0291 0.5260 0.034 Uiso 1 1 calc R . . C10 C 0.7571(3) 1.1608(3) 0.51385(16) 0.0271(4) Uani 1 1 d . . . H10 H 0.7405 1.1356 0.4361 0.032 Uiso 1 1 calc R . . C11 C 0.6413(3) 1.2872(3) 0.55273(16) 0.0275(4) Uani 1 1 d . . . H11 H 0.5545 1.3424 0.4987 0.033 Uiso 1 1 calc R . . C12 C 0.6290(3) 1.3545(3) 0.67024(17) 0.0264(4) Uani 1 1 d . . . H12A H 0.6182 1.5082 0.6729 0.032 Uiso 1 1 calc R . . H12B H 0.7373 1.3145 0.7173 0.032 Uiso 1 1 calc R . . C13 C 0.4732(2) 1.2553(3) 0.71609(15) 0.0220(4) Uani 1 1 d . . . H13 H 0.3748 1.2390 0.6554 0.026 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 0.0337(8) 0.0331(7) 0.0295(7) 0.0031(6) 0.0027(6) 0.0069(7) O2 0.0279(7) 0.0275(7) 0.0262(7) -0.0083(6) 0.0038(5) 0.0008(6) O3 0.0216(6) 0.0241(6) 0.0237(6) -0.0008(5) 0.0035(5) 0.0011(5) O4 0.0259(7) 0.0883(15) 0.0231(7) 0.0064(9) 0.0007(5) 0.0101(10) C1 0.0293(9) 0.0239(9) 0.0268(9) -0.0033(7) 0.0054(7) 0.0027(8) C2 0.0429(12) 0.0444(12) 0.0241(9) -0.0032(9) 0.0083(8) 0.0108(10) C3 0.0382(11) 0.0475(12) 0.0186(9) 0.0035(9) 0.0063(8) 0.0089(10) C4 0.0262(9) 0.0354(11) 0.0309(9) 0.0069(8) 0.0073(7) 0.0011(8) C5 0.0251(9) 0.0245(9) 0.0275(9) 0.0010(7) 0.0042(7) -0.0027(8) C6 0.0231(8) 0.0228(9) 0.0199(8) -0.0008(7) 0.0034(6) 0.0008(7) C7 0.0242(8) 0.0331(10) 0.0237(8) 0.0081(8) 0.0049(6) 0.0028(8) C8 0.0272(9) 0.0307(9) 0.0297(9) 0.0049(8) 0.0107(7) 0.0044(8) C9 0.0257(9) 0.0311(9) 0.0288(9) 0.0026(8) 0.0086(7) -0.0012(8) C10 0.0312(10) 0.0303(9) 0.0205(8) 0.0049(7) 0.0065(7) -0.0031(8) C11 0.0322(10) 0.0269(9) 0.0237(9) 0.0065(8) 0.0044(7) -0.0024(8) C12 0.0282(9) 0.0221(8) 0.0296(9) -0.0022(7) 0.0067(7) -0.0043(7) C13 0.0247(8) 0.0203(8) 0.0211(8) -0.0020(7) 0.0030(6) 0.0003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.190(3) . ? O2 C1 1.363(2) . ? O2 C13 1.452(2) . ? O3 C7 1.346(2) . ? O3 C6 1.438(2) . ? O4 C7 1.194(3) . ? C1 C2 1.500(3) . ? C2 C3 1.547(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.504(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.333(3) . ? C4 H4 0.9500 . ? C5 C6 1.494(3) . ? C5 H5 0.9500 . ? C6 C13 1.541(3) . ? C6 H6 1.0000 . ? C7 C8 1.500(3) . ? C8 C9 1.555(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.498(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.333(3) . ? C10 H10 0.9500 . ? C11 C12 1.502(3) . ? C11 H11 0.9500 . ? C12 C13 1.522(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13 1.0000 . ? 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 C1 O2 C13 116.44(15) . . ? C7 O3 C6 116.60(15) . . ? O1 C1 O2 122.52(18) . . ? O1 C1 C2 126.7(2) . . ? O2 C1 C2 110.76(17) . . ? C1 C2 C3 109.06(18) . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C2 111.25(19) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 126.4(2) . . ? C5 C4 H4 116.8 . . ? C3 C4 H4 116.8 . . ? C4 C5 C6 126.04(19) . . ? C4 C5 H5 117.0 . . ? C6 C5 H5 117.0 . . ? O3 C6 C5 109.21(16) . . ? O3 C6 C13 106.81(14) . . ? C5 C6 C13 113.40(17) . . ? O3 C6 H6 109.1 . . ? C5 C6 H6 109.1 . . ? C13 C6 H6 109.1 . . ? O4 C7 O3 123.19(19) . . ? O4 C7 C8 125.24(19) . . ? O3 C7 C8 111.43(16) . . ? C7 C8 C9 107.09(18) . . ? C7 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? C7 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C10 C9 C8 114.01(18) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 128.41(19) . . ? C11 C10 H10 115.8 . . ? C9 C10 H10 115.8 . . ? C10 C11 C12 128.93(19) . . ? C10 C11 H11 115.5 . . ? C12 C11 H11 115.5 . . ? C11 C12 C13 111.41(16) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? O2 C13 C12 109.73(15) . . ? O2 C13 C6 102.75(14) . . ? C12 C13 C6 114.38(16) . . ? O2 C13 H13 109.9 . . ? C12 C13 H13 109.9 . . ? C6 C13 H13 109.9 . . ? 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 C13 O2 C1 O1 -48.1(3) . . . . ? C13 O2 C1 C2 129.77(19) . . . . ? O1 C1 C2 C3 126.5(2) . . . . ? O2 C1 C2 C3 -51.3(3) . . . . ? C1 C2 C3 C4 -49.0(3) . . . . ? C2 C3 C4 C5 87.7(3) . . . . ? C3 C4 C5 C6 2.1(4) . . . . ? C7 O3 C6 C5 -130.66(18) . . . . ? C7 O3 C6 C13 106.34(18) . . . . ? C4 C5 C6 O3 162.68(19) . . . . ? C4 C5 C6 C13 -78.3(3) . . . . ? C6 O3 C7 O4 20.5(3) . . . . ? C6 O3 C7 C8 -155.38(17) . . . . ? O4 C7 C8 C9 -89.8(3) . . . . ? O3 C7 C8 C9 85.9(2) . . . . ? C7 C8 C9 C10 -75.6(2) . . . . ? C8 C9 C10 C11 85.4(3) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? C10 C11 C12 C13 -109.0(2) . . . . ? C1 O2 C13 C12 144.42(17) . . . . ? C1 O2 C13 C6 -93.53(18) . . . . ? C11 C12 C13 O2 -154.87(16) . . . . ? C11 C12 C13 C6 90.3(2) . . . . ? O3 C6 C13 O2 -168.45(14) . . . . ? C5 C6 C13 O2 71.20(18) . . . . ? O3 C6 C13 C12 -49.6(2) . . . . ? C5 C6 C13 C12 -169.95(16) . . . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 29.63 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.317 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.048 # Attachment 'lactone 61 cif.cif' data_ah9916 _database_code_depnum_ccdc_archive 'CCDC 655150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H16 O4' _chemical_formula_sum 'C11 H16 O4' _chemical_formula_weight 212.24 _chemical_absolute_configuration ; 1352 Friedel pairs were averaged for the refinement. ; 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 hexagonal _symmetry_space_group_name_H-M P6(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 14.3428(7) _cell_length_b 14.3428(7) _cell_length_c 8.9246(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1589.96(13) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9639 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 29.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6884 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS, Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'Thin slice, \w-scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 10627 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 29.40 _reflns_number_total 1632 _reflns_number_gt 1579 _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^)+(0.0491P)^2^+0.2113P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(10) _refine_ls_number_reflns 1632 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.38250(11) 0.34796(10) 0.94431(15) 0.0258(3) Uani 1 1 d . . . O2 O 0.38757(9) 0.34227(8) 0.69211(13) 0.0188(2) Uani 1 1 d . . . O3 O 0.17423(11) 0.10216(9) 0.52287(15) 0.0247(3) Uani 1 1 d . . . H3 H 0.1680 0.0978 0.4292 0.037 Uiso 1 1 calc R . . O4 O 0.07218(9) 0.16189(10) 0.72153(14) 0.0230(2) Uani 1 1 d . . . H4 H 0.0160 0.1163 0.6773 0.034 Uiso 1 1 calc R . . C1 C 0.41310(12) 0.39282(12) 0.8257(2) 0.0189(3) Uani 1 1 d . . . C2 C 0.47824(13) 0.51289(12) 0.8053(2) 0.0227(3) Uani 1 1 d . . . H2A H 0.5288 0.5305 0.7204 0.027 Uiso 1 1 calc R . . H2B H 0.5207 0.5469 0.8969 0.027 Uiso 1 1 calc R . . C3 C 0.40053(13) 0.55597(12) 0.7738(2) 0.0215(3) Uani 1 1 d . . . H3A H 0.3419 0.5256 0.8489 0.026 Uiso 1 1 calc R . . H3B H 0.4401 0.6352 0.7860 0.026 Uiso 1 1 calc R . . C4 C 0.35211(13) 0.52871(12) 0.6198(2) 0.0212(3) Uani 1 1 d . . . H4A H 0.3908 0.5785 0.5420 0.025 Uiso 1 1 calc R . . C5 C 0.26013(13) 0.44136(13) 0.58185(19) 0.0203(3) Uani 1 1 d . . . H5A H 0.2400 0.4347 0.4793 0.024 Uiso 1 1 calc R . . C6 C 0.18488(12) 0.35222(12) 0.68451(18) 0.0197(3) Uani 1 1 d . . . H6A H 0.1228 0.3618 0.7085 0.024 Uiso 1 1 calc R . . H6B H 0.2228 0.3570 0.7794 0.024 Uiso 1 1 calc R . . C7 C 0.14357(12) 0.24073(12) 0.61591(17) 0.0182(3) Uani 1 1 d . . . H7A H 0.1001 0.2357 0.5255 0.022 Uiso 1 1 calc R . . C8 C 0.22930(12) 0.21255(12) 0.56630(18) 0.0176(3) Uani 1 1 d . . . H8A H 0.2686 0.2577 0.4775 0.021 Uiso 1 1 calc R . . C9 C 0.31167(12) 0.22813(11) 0.68811(17) 0.0180(3) Uani 1 1 d . . . H9A H 0.2744 0.2046 0.7871 0.022 Uiso 1 1 calc R . . C10 C 0.37093(15) 0.16859(13) 0.6563(2) 0.0239(3) Uani 1 1 d . . . H10A H 0.3291 0.0931 0.6409 0.029 Uiso 1 1 calc R . . C11 C 0.47610(16) 0.21300(16) 0.6480(2) 0.0313(4) Uani 1 1 d . . . H11A H 0.5206 0.2883 0.6627 0.038 Uiso 1 1 calc R . . H11B H 0.5076 0.1698 0.6273 0.038 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 0.0318(6) 0.0234(5) 0.0236(6) -0.0013(4) -0.0047(5) 0.0148(5) O2 0.0196(5) 0.0144(4) 0.0204(5) -0.0008(4) 0.0002(4) 0.0071(4) O3 0.0348(6) 0.0148(5) 0.0178(5) -0.0023(4) -0.0026(5) 0.0072(4) O4 0.0173(5) 0.0228(5) 0.0191(5) 0.0017(4) 0.0007(4) 0.0027(4) C1 0.0167(6) 0.0182(6) 0.0247(7) -0.0025(6) -0.0048(5) 0.0108(5) C2 0.0173(6) 0.0165(6) 0.0323(8) -0.0024(6) -0.0037(6) 0.0070(5) C3 0.0226(7) 0.0154(6) 0.0275(8) -0.0004(6) -0.0003(6) 0.0103(5) C4 0.0233(7) 0.0180(6) 0.0258(7) 0.0043(6) 0.0023(6) 0.0128(6) C5 0.0231(7) 0.0209(7) 0.0219(7) 0.0027(6) 0.0008(6) 0.0146(6) C6 0.0175(6) 0.0206(6) 0.0213(7) -0.0001(5) 0.0000(5) 0.0098(5) C7 0.0162(6) 0.0182(6) 0.0164(6) 0.0010(5) -0.0012(5) 0.0056(5) C8 0.0201(6) 0.0139(6) 0.0157(6) 0.0001(5) 0.0000(5) 0.0063(5) C9 0.0203(6) 0.0133(5) 0.0190(7) 0.0003(5) -0.0003(5) 0.0074(5) C10 0.0300(8) 0.0187(7) 0.0265(8) -0.0002(6) -0.0013(6) 0.0149(6) C11 0.0323(9) 0.0299(8) 0.0392(11) 0.0024(8) 0.0053(8) 0.0211(8) _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 C1 1.202(2) . ? O2 C1 1.348(2) . ? O2 C9 1.4437(17) . ? O3 C8 1.4250(18) . ? O3 H3 0.8400 . ? O4 C7 1.4345(19) . ? O4 H4 0.8400 . ? C1 C2 1.504(2) . ? C2 C3 1.547(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.501(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.331(2) . ? C4 H4A 0.9500 . ? C5 C6 1.503(2) . ? C5 H5A 0.9500 . ? C6 C7 1.528(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.539(2) . ? C7 H7A 1.0000 . ? C8 C9 1.537(2) . ? C8 H8A 1.0000 . ? C9 C10 1.503(2) . ? C9 H9A 1.0000 . ? C10 C11 1.314(3) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C11 H11B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C9 118.69(12) . . ? C8 O3 H3 109.5 . . ? C7 O4 H4 109.5 . . ? O1 C1 O2 124.26(13) . . ? O1 C1 C2 124.82(15) . . ? O2 C1 C2 110.79(14) . . ? C1 C2 C3 108.68(13) . . ? C1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C2 113.21(14) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 126.13(15) . . ? C5 C4 H4A 116.9 . . ? C3 C4 H4A 116.9 . . ? C4 C5 C6 126.72(16) . . ? C4 C5 H5A 116.6 . . ? C6 C5 H5A 116.6 . . ? C5 C6 C7 112.56(13) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? O4 C7 C6 108.18(13) . . ? O4 C7 C8 109.34(12) . . ? C6 C7 C8 116.58(12) . . ? O4 C7 H7A 107.5 . . ? C6 C7 H7A 107.5 . . ? C8 C7 H7A 107.5 . . ? O3 C8 C9 108.21(12) . . ? O3 C8 C7 107.35(12) . . ? C9 C8 C7 114.54(13) . . ? O3 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? O2 C9 C10 109.21(12) . . ? O2 C9 C8 105.74(11) . . ? C10 C9 C8 113.30(13) . . ? O2 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C11 C10 C9 125.01(15) . . ? C11 C10 H10A 117.5 . . ? C9 C10 H10A 117.5 . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O2 C1 O1 5.3(2) . . . . ? C9 O2 C1 C2 -170.70(12) . . . . ? O1 C1 C2 C3 -93.51(19) . . . . ? O2 C1 C2 C3 82.51(16) . . . . ? C1 C2 C3 C4 -72.96(18) . . . . ? C2 C3 C4 C5 90.84(19) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C7 -136.91(16) . . . . ? C5 C6 C7 O4 -179.52(12) . . . . ? C5 C6 C7 C8 56.83(18) . . . . ? O4 C7 C8 O3 50.19(16) . . . . ? C6 C7 C8 O3 173.24(13) . . . . ? O4 C7 C8 C9 -69.98(16) . . . . ? C6 C7 C8 C9 53.07(18) . . . . ? C1 O2 C9 C10 -106.59(14) . . . . ? C1 O2 C9 C8 131.18(13) . . . . ? O3 C8 C9 O2 161.44(12) . . . . ? C7 C8 C9 O2 -78.86(15) . . . . ? O3 C8 C9 C10 41.86(17) . . . . ? C7 C8 C9 C10 161.56(12) . . . . ? O2 C9 C10 C11 6.0(2) . . . . ? C8 C9 C10 C11 123.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 29.40 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.303 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.037