# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_xs_fp _database_code_depnum_ccdc_archive 'CCDC 879025' #TrackingRef 'web_deposit_cif_file_0_xuesongxu_1335513864.compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 O4' _chemical_formula_weight 314.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3712(7) _cell_length_b 8.0916(8) _cell_length_c 13.8262(13) _cell_angle_alpha 94.596(2) _cell_angle_beta 98.403(2) _cell_angle_gamma 90.318(2) _cell_volume 813.06(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9824 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11372 _diffrn_reflns_av_R_equivalents 0.0837 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2925 _reflns_number_gt 2030 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker,2003) _computing_cell_refinement SAINT(Bruker,2001) _computing_data_reduction APEX2(Bruker,2003) _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics DIAMOND _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0989P)^2^+0.1679P] 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 0.050(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2925 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1845 _refine_ls_wR_factor_gt 0.1658 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 -0.3711(2) -0.0541(2) -0.35501(14) 0.0418(5) Uani 1 1 d . . . O2 O -0.2601(2) -0.1421(2) -0.15074(13) 0.0373(5) Uani 1 1 d . . . O3 O -0.6733(3) -0.0220(3) -0.36501(17) 0.0589(6) Uani 1 1 d . . . O4 O 0.0479(3) -0.6213(3) -0.14375(18) 0.0707(7) Uani 1 1 d . . . C1 C -0.5247(4) -0.0069(3) -0.3168(2) 0.0409(7) Uani 1 1 d . . . C2 C -0.4709(4) 0.0575(3) -0.2135(2) 0.0373(7) Uani 1 1 d . . . C3 C -0.2745(4) 0.0189(3) -0.1871(2) 0.0369(7) Uani 1 1 d . . . H3A H -0.2055 0.1053 -0.1427 0.044 Uiso 1 1 calc R . . C4 C -0.2066(3) -0.0071(3) -0.28602(19) 0.0355(6) Uani 1 1 d . . . H4A H -0.1510 0.0950 -0.3029 0.043 Uiso 1 1 calc R . . C5 C -0.0642(3) -0.1436(3) -0.27273(19) 0.0342(6) Uani 1 1 d . . . H5A H 0.0588 -0.0927 -0.2620 0.041 Uiso 1 1 calc R . . C6 C -0.0705(3) -0.2908(3) -0.35238(18) 0.0336(6) Uani 1 1 d . . . C7 C 0.1134(4) -0.3737(4) -0.3344(2) 0.0423(7) Uani 1 1 d . . . H7A H 0.2004 -0.3524 -0.3744 0.051 Uiso 1 1 calc R . . C8 C 0.1563(4) -0.4750(4) -0.2645(2) 0.0486(8) Uani 1 1 d . . . H8A H 0.2714 -0.5229 -0.2563 0.058 Uiso 1 1 calc R . . C9 C 0.0233(4) -0.5121(4) -0.1997(2) 0.0434(7) Uani 1 1 d . . . C10 C -0.1506(3) -0.4084(3) -0.21011(19) 0.0338(6) Uani 1 1 d . . . C11 C -0.0980(3) -0.2221(3) -0.17817(19) 0.0338(6) Uani 1 1 d . . . C12 C -0.2172(3) -0.4058(3) -0.32183(18) 0.0323(6) Uani 1 1 d . . . H12A H -0.3346 -0.3486 -0.3302 0.039 Uiso 1 1 calc R . . C13 C -0.2444(4) -0.5721(3) -0.3780(2) 0.0404(7) Uani 1 1 d . . . H13A H -0.1399 -0.6322 -0.3865 0.048 Uiso 1 1 calc R . . C14 C -0.4011(5) -0.6393(4) -0.4158(2) 0.0558(9) Uani 1 1 d . . . H14A H -0.5089 -0.5834 -0.4089 0.067 Uiso 1 1 calc R . . H14B H -0.4059 -0.7436 -0.4497 0.067 Uiso 1 1 calc R . . C15 C -0.5874(4) 0.1345(3) -0.1609(2) 0.0424(7) Uani 1 1 d . . . H15A H -0.7070 0.1453 -0.1919 0.051 Uiso 1 1 calc R . . C16 C -0.5453(5) 0.2039(4) -0.0587(2) 0.0563(9) Uani 1 1 d . . . H16A H -0.6535 0.2525 -0.0382 0.084 Uiso 1 1 calc R . . H16B H -0.4505 0.2874 -0.0534 0.084 Uiso 1 1 calc R . . H16C H -0.5044 0.1173 -0.0176 0.084 Uiso 1 1 calc R . . C17 C -0.1075(4) -0.2447(4) -0.4582(2) 0.0463(7) Uani 1 1 d . . . H17A H -0.0102 -0.1736 -0.4706 0.069 Uiso 1 1 calc R . . H17B H -0.2218 -0.1879 -0.4687 0.069 Uiso 1 1 calc R . . H17C H -0.1136 -0.3436 -0.5020 0.069 Uiso 1 1 calc R . . C18 C -0.2910(4) -0.4781(3) -0.1532(2) 0.0452(7) Uani 1 1 d . . . H18A H -0.3170 -0.5923 -0.1758 0.068 Uiso 1 1 calc R . . H18B H -0.4017 -0.4159 -0.1633 0.068 Uiso 1 1 calc R . . H18C H -0.2429 -0.4702 -0.0846 0.068 Uiso 1 1 calc R . . C19 C 0.0551(4) -0.1953(4) -0.0925(2) 0.0510(8) Uani 1 1 d . . . H19A H 0.0784 -0.0786 -0.0773 0.077 Uiso 1 1 calc R . . H19B H 0.1641 -0.2475 -0.1093 0.077 Uiso 1 1 calc R . . H19C H 0.0198 -0.2428 -0.0364 0.077 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 0.0461(11) 0.0404(11) 0.0390(11) 0.0033(9) 0.0065(8) 0.0074(8) O2 0.0424(10) 0.0345(10) 0.0386(11) 0.0052(8) 0.0158(8) 0.0109(8) O3 0.0441(13) 0.0662(15) 0.0630(15) 0.0032(12) -0.0025(11) 0.0032(10) O4 0.0755(17) 0.0676(16) 0.0769(17) 0.0337(14) 0.0209(13) 0.0350(13) C1 0.0439(16) 0.0302(14) 0.0491(18) 0.0057(12) 0.0075(13) 0.0043(12) C2 0.0397(14) 0.0288(14) 0.0445(17) 0.0052(12) 0.0085(12) 0.0041(11) C3 0.0402(15) 0.0260(14) 0.0450(17) -0.0015(12) 0.0107(12) 0.0016(11) C4 0.0404(15) 0.0279(14) 0.0398(16) 0.0052(11) 0.0099(12) 0.0000(11) C5 0.0328(13) 0.0313(14) 0.0399(16) 0.0012(12) 0.0107(11) -0.0016(11) C6 0.0359(14) 0.0318(14) 0.0340(15) -0.0005(11) 0.0103(11) 0.0011(11) C7 0.0368(15) 0.0445(17) 0.0465(18) -0.0059(14) 0.0147(12) -0.0008(12) C8 0.0350(15) 0.0526(19) 0.059(2) 0.0009(16) 0.0106(13) 0.0149(13) C9 0.0452(16) 0.0375(16) 0.0471(18) 0.0043(14) 0.0043(13) 0.0127(12) C10 0.0366(14) 0.0316(14) 0.0346(15) 0.0031(11) 0.0096(11) 0.0063(11) C11 0.0333(13) 0.0356(14) 0.0325(15) -0.0013(12) 0.0067(11) 0.0050(11) C12 0.0316(13) 0.0285(13) 0.0372(15) 0.0015(11) 0.0069(11) 0.0050(10) C13 0.0468(16) 0.0324(15) 0.0417(17) 0.0003(12) 0.0072(13) 0.0041(12) C14 0.064(2) 0.0400(18) 0.059(2) -0.0038(15) -0.0007(16) -0.0047(15) C15 0.0388(15) 0.0361(15) 0.0547(19) 0.0064(13) 0.0128(13) 0.0047(12) C16 0.061(2) 0.057(2) 0.055(2) 0.0013(16) 0.0234(16) 0.0110(16) C17 0.0549(18) 0.0487(17) 0.0373(17) 0.0020(13) 0.0145(13) -0.0002(14) C18 0.0521(17) 0.0382(16) 0.0492(18) 0.0075(13) 0.0181(14) 0.0028(13) C19 0.0513(18) 0.0549(19) 0.0435(18) -0.0037(15) -0.0004(14) 0.0046(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.362(3) . ? O1 C4 1.457(3) . ? O2 C3 1.432(3) . ? O2 C11 1.446(3) . ? O3 C1 1.196(3) . ? O4 C9 1.217(3) . ? C1 C2 1.477(4) . ? C2 C15 1.330(4) . ? C2 C3 1.482(4) . ? C3 C4 1.523(4) . ? C3 H3A 0.9800 . ? C4 C5 1.531(4) . ? C4 H4A 0.9800 . ? C5 C11 1.549(4) . ? C5 C6 1.551(4) . ? C5 H5A 0.9800 . ? C6 C7 1.513(4) . ? C6 C17 1.525(4) . ? C6 C12 1.548(3) . ? C7 C8 1.321(4) . ? C7 H7A 0.9300 . ? C8 C9 1.467(4) . ? C8 H8A 0.9300 . ? C9 C10 1.531(4) . ? C10 C18 1.520(4) . ? C10 C12 1.553(4) . ? C10 C11 1.566(4) . ? C11 C19 1.513(4) . ? C12 C13 1.496(4) . ? C12 H12A 0.9800 . ? C13 C14 1.294(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? C15 C16 1.467(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 110.8(2) . . ? C3 O2 C11 109.55(18) . . ? O3 C1 O1 121.1(3) . . ? O3 C1 C2 130.1(3) . . ? O1 C1 C2 108.8(2) . . ? C15 C2 C1 122.6(3) . . ? C15 C2 C3 130.8(3) . . ? C1 C2 C3 106.6(2) . . ? O2 C3 C2 109.1(2) . . ? O2 C3 C4 103.44(19) . . ? C2 C3 C4 103.6(2) . . ? O2 C3 H3A 113.3 . . ? C2 C3 H3A 113.3 . . ? C4 C3 H3A 113.3 . . ? O1 C4 C3 104.3(2) . . ? O1 C4 C5 114.7(2) . . ? C3 C4 C5 104.6(2) . . ? O1 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? C5 C4 H4A 110.9 . . ? C4 C5 C11 105.00(19) . . ? C4 C5 C6 119.3(2) . . ? C11 C5 C6 105.36(19) . . ? C4 C5 H5A 108.9 . . ? C11 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C7 C6 C17 109.6(2) . . ? C7 C6 C12 108.3(2) . . ? C17 C6 C12 115.2(2) . . ? C7 C6 C5 106.2(2) . . ? C17 C6 C5 115.5(2) . . ? C12 C6 C5 101.35(19) . . ? C8 C7 C6 123.1(2) . . ? C8 C7 H7A 118.5 . . ? C6 C7 H7A 118.5 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? O4 C9 C8 122.0(3) . . ? O4 C9 C10 122.7(3) . . ? C8 C9 C10 115.3(2) . . ? C18 C10 C9 110.3(2) . . ? C18 C10 C12 114.2(2) . . ? C9 C10 C12 106.5(2) . . ? C18 C10 C11 113.4(2) . . ? C9 C10 C11 109.3(2) . . ? C12 C10 C11 102.62(19) . . ? O2 C11 C19 108.2(2) . . ? O2 C11 C5 104.79(19) . . ? C19 C11 C5 115.3(2) . . ? O2 C11 C10 107.36(19) . . ? C19 C11 C10 114.6(2) . . ? C5 C11 C10 105.9(2) . . ? C13 C12 C6 115.8(2) . . ? C13 C12 C10 115.5(2) . . ? C6 C12 C10 101.35(19) . . ? C13 C12 H12A 107.9 . . ? C6 C12 H12A 107.9 . . ? C10 C12 H12A 107.9 . . ? C14 C13 C12 125.5(3) . . ? C14 C13 H13A 117.3 . . ? C12 C13 H13A 117.3 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C2 C15 C16 126.2(3) . . ? C2 C15 H15A 116.9 . . ? C16 C15 H15A 116.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 C17 H17A 109.5 . . ? C6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C10 C18 H18A 109.5 . . ? C10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C4 O1 C1 O3 173.8(2) . . . . ? C4 O1 C1 C2 -6.9(3) . . . . ? O3 C1 C2 C15 -10.5(5) . . . . ? O1 C1 C2 C15 170.3(2) . . . . ? O3 C1 C2 C3 169.8(3) . . . . ? O1 C1 C2 C3 -9.5(3) . . . . ? C11 O2 C3 C2 146.6(2) . . . . ? C11 O2 C3 C4 36.8(3) . . . . ? C15 C2 C3 O2 91.4(3) . . . . ? C1 C2 C3 O2 -88.9(2) . . . . ? C15 C2 C3 C4 -158.9(3) . . . . ? C1 C2 C3 C4 20.8(3) . . . . ? C1 O1 C4 C3 19.8(3) . . . . ? C1 O1 C4 C5 133.6(2) . . . . ? O2 C3 C4 O1 89.5(2) . . . . ? C2 C3 C4 O1 -24.3(2) . . . . ? O2 C3 C4 C5 -31.3(2) . . . . ? C2 C3 C4 C5 -145.1(2) . . . . ? O1 C4 C5 C11 -98.0(2) . . . . ? C3 C4 C5 C11 15.6(2) . . . . ? O1 C4 C5 C6 19.7(3) . . . . ? C3 C4 C5 C6 133.3(2) . . . . ? C4 C5 C6 C7 163.8(2) . . . . ? C11 C5 C6 C7 -78.7(2) . . . . ? C4 C5 C6 C17 42.1(3) . . . . ? C11 C5 C6 C17 159.6(2) . . . . ? C4 C5 C6 C12 -83.1(3) . . . . ? C11 C5 C6 C12 34.4(2) . . . . ? C17 C6 C7 C8 -156.4(3) . . . . ? C12 C6 C7 C8 -29.9(4) . . . . ? C5 C6 C7 C8 78.2(3) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 O4 169.8(3) . . . . ? C7 C8 C9 C10 -8.2(4) . . . . ? O4 C9 C10 C18 -8.0(4) . . . . ? C8 C9 C10 C18 170.0(3) . . . . ? O4 C9 C10 C12 -132.4(3) . . . . ? C8 C9 C10 C12 45.5(3) . . . . ? O4 C9 C10 C11 117.4(3) . . . . ? C8 C9 C10 C11 -64.7(3) . . . . ? C3 O2 C11 C19 96.8(2) . . . . ? C3 O2 C11 C5 -26.7(2) . . . . ? C3 O2 C11 C10 -139.0(2) . . . . ? C4 C5 C11 O2 5.5(2) . . . . ? C6 C5 C11 O2 -121.3(2) . . . . ? C4 C5 C11 C19 -113.3(2) . . . . ? C6 C5 C11 C19 119.9(2) . . . . ? C4 C5 C11 C10 118.8(2) . . . . ? C6 C5 C11 C10 -7.9(2) . . . . ? C18 C10 C11 O2 -33.7(3) . . . . ? C9 C10 C11 O2 -157.2(2) . . . . ? C12 C10 C11 O2 90.0(2) . . . . ? C18 C10 C11 C19 86.5(3) . . . . ? C9 C10 C11 C19 -37.0(3) . . . . ? C12 C10 C11 C19 -149.8(2) . . . . ? C18 C10 C11 C5 -145.3(2) . . . . ? C9 C10 C11 C5 91.2(2) . . . . ? C12 C10 C11 C5 -21.5(2) . . . . ? C7 C6 C12 C13 -62.2(3) . . . . ? C17 C6 C12 C13 60.9(3) . . . . ? C5 C6 C12 C13 -173.6(2) . . . . ? C7 C6 C12 C10 63.6(2) . . . . ? C17 C6 C12 C10 -173.3(2) . . . . ? C5 C6 C12 C10 -47.9(2) . . . . ? C18 C10 C12 C13 -67.9(3) . . . . ? C9 C10 C12 C13 54.1(3) . . . . ? C11 C10 C12 C13 168.9(2) . . . . ? C18 C10 C12 C6 166.1(2) . . . . ? C9 C10 C12 C6 -71.9(2) . . . . ? C11 C10 C12 C6 42.9(2) . . . . ? C6 C12 C13 C14 -132.2(3) . . . . ? C10 C12 C13 C14 109.5(3) . . . . ? C1 C2 C15 C16 -179.2(3) . . . . ? C3 C2 C15 C16 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.324 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.058 data_xs-1-8-a1 _database_code_depnum_ccdc_archive 'CCDC 879026' #TrackingRef 'web_deposit_cif_file_1_xuesongxu_1335513864.compound 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 O4' _chemical_formula_weight 256.33 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 P3(2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' _cell_length_a 14.4194(18) _cell_length_b 14.4194(18) _cell_length_c 6.0541(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1090.1(2) _cell_formula_units_Z 3 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9752 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21605 _diffrn_reflns_av_R_equivalents 0.1038 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2584 _reflns_number_gt 1678 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker,2003) _computing_cell_refinement SAINT(Bruker,2001) _computing_data_reduction APEX2(Bruker,2003) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND _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^)+(0.0643P)^2^+0.0795P] 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 0.016(4) _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 1.4(18) _refine_ls_number_reflns 2584 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.5921(3) 0.1488(3) 0.0641(6) 0.0660(9) Uani 1 1 d . . . H1A H 0.5701 0.1319 -0.0906 0.079 Uiso 1 1 calc R . . C2 C 0.6821(3) 0.1244(3) 0.1045(5) 0.0592(8) Uani 1 1 d . . . H2A H 0.7350 0.1622 -0.0120 0.071 Uiso 1 1 calc R . . C3 C 0.6392(2) 0.0055(2) 0.0627(5) 0.0487(7) Uani 1 1 d . . . H3A H 0.6150 -0.0060 -0.0913 0.058 Uiso 1 1 calc R . . C4 C 0.7233(3) -0.0291(3) 0.0730(5) 0.0576(8) Uani 1 1 d . . . H4A H 0.7517 -0.0205 0.2233 0.069 Uiso 1 1 calc R . . C5 C 0.6796(3) -0.1427(3) -0.0043(6) 0.0743(10) Uani 1 1 d . . . H5A H 0.7325 -0.1642 0.0223 0.089 Uiso 1 1 calc R . . H5B H 0.6668 -0.1462 -0.1622 0.089 Uiso 1 1 calc R . . C6 C 0.5758(3) -0.2207(3) 0.1121(6) 0.0748(10) Uani 1 1 d . . . H6A H 0.5462 -0.2908 0.0445 0.090 Uiso 1 1 calc R . . H6B H 0.5906 -0.2270 0.2660 0.090 Uiso 1 1 calc R . . C7 C 0.4959(3) -0.1834(3) 0.0981(5) 0.0631(9) Uani 1 1 d . . . H7A H 0.4812 -0.1792 -0.0585 0.076 Uiso 1 1 calc R . . C8 C 0.5380(2) -0.0719(2) 0.1993(5) 0.0533(8) Uani 1 1 d . . . C9 C 0.4539(3) -0.0376(3) 0.1644(6) 0.0699(10) Uani 1 1 d . . . H9A H 0.4277 -0.0544 0.0138 0.084 Uiso 1 1 calc R . . H9B H 0.3938 -0.0793 0.2621 0.084 Uiso 1 1 calc R . . C10 C 0.4955(3) 0.0811(3) 0.2062(7) 0.0799(11) Uani 1 1 d . . . H10A H 0.4396 0.0978 0.1731 0.096 Uiso 1 1 calc R . . H10B H 0.5146 0.0973 0.3607 0.096 Uiso 1 1 calc R . . C11 C 0.7415(3) 0.1704(3) 0.3244(7) 0.0835(12) Uani 1 1 d . . . H11A H 0.7975 0.1532 0.3404 0.125 Uiso 1 1 calc R . . H11B H 0.6920 0.1398 0.4450 0.125 Uiso 1 1 calc R . . H11C H 0.7720 0.2467 0.3249 0.125 Uiso 1 1 calc R . . C12 C 0.9099(3) 0.0843(3) -0.0122(8) 0.0788(11) Uani 1 1 d . . . C13 C 0.9858(4) 0.1456(4) -0.1933(9) 0.1038(14) Uani 1 1 d . . . H13A H 1.0580 0.1765 -0.1402 0.156 Uiso 1 1 calc R . . H13B H 0.9729 0.2015 -0.2423 0.156 Uiso 1 1 calc R . . H13C H 0.9754 0.0983 -0.3144 0.156 Uiso 1 1 calc R . . C14 C 0.5576(3) -0.0740(3) 0.4462(5) 0.0733(10) Uani 1 1 d . . . H14A H 0.4916 -0.1229 0.5181 0.110 Uiso 1 1 calc R . . H14B H 0.5848 -0.0036 0.5066 0.110 Uiso 1 1 calc R . . H14C H 0.6089 -0.0970 0.4694 0.110 Uiso 1 1 calc R . . O1 O 0.6235(2) 0.2576(2) 0.0994(5) 0.0929(9) Uani 1 1 d . . . H1B H 0.6609 0.2937 -0.0038 0.139 Uiso 1 1 calc R . . O2 O 0.80811(18) 0.0389(2) -0.0796(4) 0.0703(7) Uani 1 1 d . . . O3 O 0.9356(2) 0.0736(3) 0.1694(6) 0.1124(12) Uani 1 1 d . . . O4 O 0.39635(19) -0.25916(19) 0.2025(4) 0.0801(8) Uani 1 1 d . . . H4C H 0.4084 -0.2900 0.3025 0.120 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 C1 0.073(2) 0.056(2) 0.069(2) 0.0045(16) 0.0128(17) 0.0319(19) C2 0.0558(19) 0.056(2) 0.055(2) 0.0022(14) 0.0043(15) 0.0201(16) C3 0.0530(18) 0.0507(18) 0.0390(15) 0.0000(13) -0.0050(12) 0.0232(15) C4 0.060(2) 0.066(2) 0.0501(18) 0.0112(15) 0.0009(14) 0.0341(19) C5 0.089(3) 0.072(2) 0.070(2) 0.0085(18) -0.001(2) 0.047(2) C6 0.095(3) 0.052(2) 0.074(2) 0.0055(17) -0.008(2) 0.033(2) C7 0.066(2) 0.054(2) 0.0463(19) 0.0084(14) -0.0078(15) 0.0122(18) C8 0.0513(19) 0.0547(19) 0.0425(18) 0.0047(13) -0.0034(13) 0.0179(15) C9 0.051(2) 0.074(2) 0.071(2) 0.0026(18) 0.0066(16) 0.0211(18) C10 0.070(2) 0.080(3) 0.096(3) 0.005(2) 0.018(2) 0.042(2) C11 0.078(3) 0.073(3) 0.077(3) -0.022(2) -0.011(2) 0.021(2) C12 0.063(3) 0.075(3) 0.095(3) 0.004(2) 0.001(2) 0.032(2) C13 0.078(3) 0.095(3) 0.125(4) 0.017(3) 0.034(3) 0.032(3) C14 0.080(2) 0.076(2) 0.0430(19) 0.0052(16) -0.0009(16) 0.024(2) O1 0.121(2) 0.0665(17) 0.100(2) 0.0059(14) 0.0288(17) 0.0532(17) O2 0.0560(15) 0.0869(18) 0.0692(15) 0.0213(12) 0.0115(11) 0.0366(14) O3 0.0678(19) 0.125(3) 0.109(3) 0.0137(19) -0.0150(17) 0.0223(18) O4 0.0726(16) 0.0612(15) 0.0676(16) 0.0237(11) -0.0080(12) 0.0043(13) _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 C1 O1 1.415(4) . ? C1 C10 1.508(5) . ? C1 C2 1.524(5) . ? C2 C3 1.524(4) . ? C2 C11 1.542(5) . ? C3 C4 1.526(4) . ? C3 C8 1.559(4) . ? C4 O2 1.453(4) . ? C4 C5 1.506(5) . ? C5 C6 1.522(5) . ? C6 C7 1.498(5) . ? C7 O4 1.444(4) . ? C7 C8 1.535(4) . ? C8 C14 1.525(4) . ? C8 C9 1.535(5) . ? C9 C10 1.526(5) . ? C12 O3 1.194(5) . ? C12 O2 1.338(5) . ? C12 C13 1.488(6) . ? 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 O1 C1 C10 108.1(3) . . ? O1 C1 C2 113.3(3) . . ? C10 C1 C2 112.2(3) . . ? C3 C2 C1 108.6(3) . . ? C3 C2 C11 116.9(3) . . ? C1 C2 C11 113.1(3) . . ? C2 C3 C4 114.7(3) . . ? C2 C3 C8 115.2(3) . . ? C4 C3 C8 110.9(2) . . ? O2 C4 C5 106.9(3) . . ? O2 C4 C3 107.0(2) . . ? C5 C4 C3 112.0(3) . . ? C4 C5 C6 112.4(3) . . ? C7 C6 C5 111.0(3) . . ? O4 C7 C6 110.9(3) . . ? O4 C7 C8 109.9(3) . . ? C6 C7 C8 112.4(3) . . ? C14 C8 C7 110.5(3) . . ? C14 C8 C9 109.0(3) . . ? C7 C8 C9 108.7(3) . . ? C14 C8 C3 114.7(3) . . ? C7 C8 C3 106.1(2) . . ? C9 C8 C3 107.7(2) . . ? C10 C9 C8 114.0(3) . . ? C1 C10 C9 110.4(3) . . ? O3 C12 O2 123.6(4) . . ? O3 C12 C13 124.9(4) . . ? O2 C12 C13 111.5(4) . . ? C12 O2 C4 118.9(3) . . ? 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 O1 C1 C2 C3 179.7(3) . . . . ? C10 C1 C2 C3 57.1(3) . . . . ? O1 C1 C2 C11 48.2(4) . . . . ? C10 C1 C2 C11 -74.5(4) . . . . ? C1 C2 C3 C4 173.9(2) . . . . ? C11 C2 C3 C4 -56.6(4) . . . . ? C1 C2 C3 C8 -55.5(3) . . . . ? C11 C2 C3 C8 73.9(4) . . . . ? C2 C3 C4 O2 -54.3(3) . . . . ? C8 C3 C4 O2 173.1(2) . . . . ? C2 C3 C4 C5 -171.0(3) . . . . ? C8 C3 C4 C5 56.3(3) . . . . ? O2 C4 C5 C6 -168.5(3) . . . . ? C3 C4 C5 C6 -51.7(4) . . . . ? C4 C5 C6 C7 52.1(4) . . . . ? C5 C6 C7 O4 178.2(3) . . . . ? C5 C6 C7 C8 -58.3(4) . . . . ? O4 C7 C8 C14 60.1(3) . . . . ? C6 C7 C8 C14 -63.9(4) . . . . ? O4 C7 C8 C9 -59.5(3) . . . . ? C6 C7 C8 C9 176.5(3) . . . . ? O4 C7 C8 C3 -175.1(2) . . . . ? C6 C7 C8 C3 60.9(3) . . . . ? C2 C3 C8 C14 -69.2(3) . . . . ? C4 C3 C8 C14 63.2(4) . . . . ? C2 C3 C8 C7 168.6(3) . . . . ? C4 C3 C8 C7 -59.0(3) . . . . ? C2 C3 C8 C9 52.4(3) . . . . ? C4 C3 C8 C9 -175.2(3) . . . . ? C14 C8 C9 C10 73.5(4) . . . . ? C7 C8 C9 C10 -166.0(3) . . . . ? C3 C8 C9 C10 -51.6(4) . . . . ? O1 C1 C10 C9 176.6(3) . . . . ? C2 C1 C10 C9 -57.9(4) . . . . ? C8 C9 C10 C1 56.0(4) . . . . ? O3 C12 O2 C4 -1.4(5) . . . . ? C13 C12 O2 C4 176.6(3) . . . . ? C5 C4 O2 C12 -107.1(3) . . . . ? C3 C4 O2 C12 132.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.033 data_a2 _database_code_depnum_ccdc_archive 'CCDC 879027' #TrackingRef 'web_deposit_cif_file_2_xuesongxu_1335513864.compound 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 O5' _chemical_formula_weight 326.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.331(2) _cell_length_b 8.783(2) _cell_length_c 13.724(4) _cell_angle_alpha 93.330(6) _cell_angle_beta 106.838(6) _cell_angle_gamma 101.942(6) _cell_volume 932.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.083 _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 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21479 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3356 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker,2003) _computing_cell_refinement SAINT(Bruker,2001) _computing_data_reduction APEX2(Bruker,2003) _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics DIAMOND _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0709P)^2^+0.4285P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3356 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 C1 C -0.1621(3) 0.8399(3) 0.14569(18) 0.0445(6) Uani 1 1 d . . . C2 C -0.2735(3) 0.7486(3) 0.2032(2) 0.0567(7) Uani 1 1 d . . . H2A H -0.3867 0.7007 0.1556 0.068 Uiso 1 1 calc R . . H2B H -0.2879 0.8203 0.2548 0.068 Uiso 1 1 calc R . . C3 C -0.1931(3) 0.6213(3) 0.2549(2) 0.0575(7) Uani 1 1 d . . . H3A H -0.1891 0.5444 0.2026 0.069 Uiso 1 1 calc R . . H3B H -0.2658 0.5683 0.2925 0.069 Uiso 1 1 calc R . . C4 C -0.0099(3) 0.6865(3) 0.32913(19) 0.0503(7) Uani 1 1 d . . . C5 C 0.0743(4) 0.5520(3) 0.3629(2) 0.0640(8) Uani 1 1 d . . . C6 C 0.2643(4) 0.5945(4) 0.4195(3) 0.0768(10) Uani 1 1 d . . . H6A H 0.3064 0.4993 0.4255 0.092 Uiso 1 1 calc R . . H6B H 0.2824 0.6431 0.4883 0.092 Uiso 1 1 calc R . . C7 C 0.3694(4) 0.7066(3) 0.3668(2) 0.0680(8) Uani 1 1 d . . . H7A H 0.4858 0.7462 0.4129 0.082 Uiso 1 1 calc R . . H7B H 0.3764 0.6500 0.3059 0.082 Uiso 1 1 calc R . . C8 C 0.2882(3) 0.8429(3) 0.33698(18) 0.0486(6) Uani 1 1 d . . . H8A H 0.2955 0.9095 0.3987 0.058 Uiso 1 1 calc R . . C9 C 0.1003(3) 0.7853(3) 0.27051(17) 0.0433(6) Uani 1 1 d . . . H9A H 0.1024 0.7111 0.2150 0.052 Uiso 1 1 calc R . . C10 C 0.0215(3) 0.9144(3) 0.21632(17) 0.0425(6) Uani 1 1 d . . . H10A H 0.0897 0.9512 0.1713 0.051 Uiso 1 1 calc R . . C11 C -0.0174(4) 0.7744(3) 0.4283(2) 0.0677(9) Uani 1 1 d . . . H11A H -0.0884 0.7050 0.4589 0.102 Uiso 1 1 calc R . . H11B H -0.0655 0.8634 0.4118 0.102 Uiso 1 1 calc R . . H11C H 0.0969 0.8090 0.4757 0.102 Uiso 1 1 calc R . . C12 C 0.0305(4) 1.0591(3) 0.2870(2) 0.0603(8) Uani 1 1 d . . . H12A H -0.0208 1.1325 0.2467 0.090 Uiso 1 1 calc R . . H12B H 0.1488 1.1074 0.3240 0.090 Uiso 1 1 calc R . . H12C H -0.0310 1.0284 0.3347 0.090 Uiso 1 1 calc R . . C13 C 0.5029(4) 1.0596(4) 0.3196(2) 0.0689(9) Uani 1 1 d . . . C14 C 0.5695(4) 1.1511(4) 0.2476(2) 0.0688(8) Uani 1 1 d . . . H14A H 0.6590 1.2401 0.2852 0.103 Uiso 1 1 calc R . . H14B H 0.4777 1.1865 0.2017 0.103 Uiso 1 1 calc R . . H14C H 0.6155 1.0866 0.2089 0.103 Uiso 1 1 calc R . . C15 C -0.2889(4) 0.6467(3) -0.0074(2) 0.0651(8) Uani 1 1 d . . . H15A H -0.3767 0.7059 -0.0285 0.078 Uiso 1 1 calc R . . H15B H -0.3350 0.5567 0.0222 0.078 Uiso 1 1 calc R . . C16 C -0.2398(5) 0.5942(4) -0.0971(2) 0.0844(11) Uani 1 1 d . . . H16A H -0.3393 0.5284 -0.1475 0.127 Uiso 1 1 calc R . . H16B H -0.1526 0.5362 -0.0755 0.127 Uiso 1 1 calc R . . H16C H -0.1959 0.6840 -0.1265 0.127 Uiso 1 1 calc R . . C17 C -0.1854(4) 1.0445(3) 0.0346(2) 0.0590(7) Uani 1 1 d . . . H17A H -0.2062 0.9803 -0.0298 0.071 Uiso 1 1 calc R . . H17B H -0.0619 1.0843 0.0650 0.071 Uiso 1 1 calc R . . C18 C -0.2711(4) 1.1776(4) 0.0156(3) 0.0758(9) Uani 1 1 d . . . H18A H -0.2268 1.2396 -0.0303 0.114 Uiso 1 1 calc R . . H18B H -0.2486 1.2415 0.0794 0.114 Uiso 1 1 calc R . . H18C H -0.3933 1.1374 -0.0146 0.114 Uiso 1 1 calc R . . O1 O -0.1369(2) 0.74361(19) 0.06677(12) 0.0484(5) Uani 1 1 d . . . O2 O -0.2533(2) 0.9524(2) 0.10237(13) 0.0521(5) Uani 1 1 d . . . O3 O -0.0083(3) 0.4172(2) 0.3470(2) 0.0952(8) Uani 1 1 d . . . O4 O 0.3787(2) 0.9337(2) 0.27518(12) 0.0527(5) Uani 1 1 d . . . O5 O 0.5539(5) 1.0917(5) 0.40867(19) 0.200(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0455(14) 0.0405(13) 0.0487(14) 0.0095(11) 0.0178(12) 0.0069(11) C2 0.0501(16) 0.0551(16) 0.0641(17) 0.0142(14) 0.0223(14) 0.0025(13) C3 0.0598(17) 0.0476(15) 0.0620(17) 0.0157(13) 0.0241(14) -0.0042(13) C4 0.0620(17) 0.0388(13) 0.0449(14) 0.0082(11) 0.0152(12) 0.0016(12) C5 0.082(2) 0.0440(16) 0.0558(17) 0.0100(13) 0.0128(15) 0.0032(15) C6 0.084(2) 0.0558(18) 0.074(2) 0.0181(16) -0.0003(18) 0.0137(17) C7 0.0685(19) 0.0648(19) 0.0604(18) 0.0060(15) 0.0031(15) 0.0176(16) C8 0.0530(15) 0.0464(14) 0.0390(13) 0.0016(11) 0.0104(12) 0.0019(12) C9 0.0500(14) 0.0364(12) 0.0392(13) 0.0006(10) 0.0126(11) 0.0039(11) C10 0.0453(14) 0.0366(13) 0.0436(13) 0.0042(10) 0.0170(11) 0.0008(11) C11 0.090(2) 0.0625(18) 0.0526(16) 0.0127(14) 0.0335(16) 0.0033(17) C12 0.0720(19) 0.0410(14) 0.0651(17) 0.0027(13) 0.0195(15) 0.0106(14) C13 0.0687(19) 0.073(2) 0.0446(16) -0.0021(14) 0.0093(14) -0.0138(16) C14 0.0640(19) 0.072(2) 0.0690(19) 0.0125(16) 0.0259(16) 0.0036(16) C15 0.0544(17) 0.0599(17) 0.0603(18) -0.0002(14) 0.0025(14) -0.0077(14) C16 0.091(2) 0.076(2) 0.064(2) -0.0180(17) 0.0107(18) -0.0031(19) C17 0.0590(17) 0.0611(17) 0.0658(17) 0.0268(14) 0.0283(14) 0.0157(14) C18 0.083(2) 0.072(2) 0.093(2) 0.0395(18) 0.0427(19) 0.0329(18) O1 0.0437(10) 0.0466(10) 0.0472(10) -0.0008(8) 0.0097(8) 0.0018(8) O2 0.0473(10) 0.0547(11) 0.0605(11) 0.0202(9) 0.0229(9) 0.0128(9) O3 0.1035(18) 0.0414(12) 0.1146(19) 0.0192(12) 0.0030(15) 0.0012(12) O4 0.0483(10) 0.0585(11) 0.0426(9) -0.0021(8) 0.0122(8) -0.0016(9) O5 0.240(4) 0.199(3) 0.0502(16) -0.0172(18) 0.027(2) -0.156(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.423(3) . ? C1 O1 1.425(3) . ? C1 C2 1.522(3) . ? C1 C10 1.536(3) . ? C2 C3 1.526(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.538(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(4) . ? C4 C11 1.549(4) . ? C4 C9 1.556(3) . ? C5 O3 1.211(3) . ? C5 C6 1.502(4) . ? C6 C7 1.534(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.513(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O4 1.457(3) . ? C8 C9 1.526(3) . ? C8 H8A 0.9800 . ? C9 C10 1.547(3) . ? C9 H9A 0.9800 . ? C10 C12 1.529(3) . ? C10 H10A 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O5 1.168(3) . ? C13 O4 1.322(3) . ? C13 C14 1.468(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O1 1.439(3) . ? C15 C16 1.483(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O2 1.429(3) . ? C17 C18 1.489(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 110.09(19) . . ? O2 C1 C2 104.7(2) . . ? O1 C1 C2 113.0(2) . . ? O2 C1 C10 113.13(19) . . ? O1 C1 C10 104.12(18) . . ? C2 C1 C10 111.9(2) . . ? C1 C2 C3 111.6(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 112.8(2) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 110.0(2) . . ? C5 C4 C11 105.9(2) . . ? C3 C4 C11 110.2(2) . . ? C5 C4 C9 107.0(2) . . ? C3 C4 C9 108.42(19) . . ? C11 C4 C9 115.2(2) . . ? O3 C5 C6 121.4(3) . . ? O3 C5 C4 121.7(3) . . ? C6 C5 C4 116.9(2) . . ? C5 C6 C7 113.2(2) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 111.2(3) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O4 C8 C7 109.0(2) . . ? O4 C8 C9 106.73(19) . . ? C7 C8 C9 111.1(2) . . ? O4 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? C8 C9 C10 113.95(19) . . ? C8 C9 C4 111.35(19) . . ? C10 C9 C4 115.0(2) . . ? C8 C9 H9A 105.1 . . ? C10 C9 H9A 105.1 . . ? C4 C9 H9A 105.1 . . ? C12 C10 C1 112.9(2) . . ? C12 C10 C9 115.5(2) . . ? C1 C10 C9 109.04(18) . . ? C12 C10 H10A 106.2 . . ? C1 C10 H10A 106.2 . . ? C9 C10 H10A 106.2 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 O4 121.6(3) . . ? O5 C13 C14 124.2(3) . . ? O4 C13 C14 114.2(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C16 108.0(2) . . ? O1 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? O1 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 C18 109.0(2) . . ? O2 C17 H17A 109.9 . . ? C18 C17 H17A 109.9 . . ? O2 C17 H17B 109.9 . . ? C18 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 O1 C15 117.1(2) . . ? C1 O2 C17 116.50(19) . . ? C13 O4 C8 119.5(2) . . ? 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 O2 C1 C2 C3 180.0(2) . . . . ? O1 C1 C2 C3 60.1(3) . . . . ? C10 C1 C2 C3 -57.1(3) . . . . ? C1 C2 C3 C4 56.9(3) . . . . ? C2 C3 C4 C5 -169.8(2) . . . . ? C2 C3 C4 C11 73.8(3) . . . . ? C2 C3 C4 C9 -53.1(3) . . . . ? C3 C4 C5 O3 -12.7(4) . . . . ? C11 C4 C5 O3 106.3(3) . . . . ? C9 C4 C5 O3 -130.2(3) . . . . ? C3 C4 C5 C6 168.9(2) . . . . ? C11 C4 C5 C6 -72.1(3) . . . . ? C9 C4 C5 C6 51.3(3) . . . . ? O3 C5 C6 C7 133.3(3) . . . . ? C4 C5 C6 C7 -48.2(4) . . . . ? C5 C6 C7 C8 47.7(3) . . . . ? C6 C7 C8 O4 -172.3(2) . . . . ? C6 C7 C8 C9 -55.0(3) . . . . ? O4 C8 C9 C10 -47.7(3) . . . . ? C7 C8 C9 C10 -166.5(2) . . . . ? O4 C8 C9 C4 -179.81(19) . . . . ? C7 C8 C9 C4 61.5(3) . . . . ? C5 C4 C9 C8 -56.8(3) . . . . ? C3 C4 C9 C8 -175.4(2) . . . . ? C11 C4 C9 C8 60.7(3) . . . . ? C5 C4 C9 C10 171.7(2) . . . . ? C3 C4 C9 C10 53.1(3) . . . . ? C11 C4 C9 C10 -70.9(3) . . . . ? O2 C1 C10 C12 42.7(3) . . . . ? O1 C1 C10 C12 162.19(19) . . . . ? C2 C1 C10 C12 -75.4(3) . . . . ? O2 C1 C10 C9 172.48(19) . . . . ? O1 C1 C10 C9 -68.0(2) . . . . ? C2 C1 C10 C9 54.4(3) . . . . ? C8 C9 C10 C12 -56.0(3) . . . . ? C4 C9 C10 C12 74.3(3) . . . . ? C8 C9 C10 C1 175.67(19) . . . . ? C4 C9 C10 C1 -54.0(3) . . . . ? O2 C1 O1 C15 -63.7(3) . . . . ? C2 C1 O1 C15 53.1(3) . . . . ? C10 C1 O1 C15 174.77(19) . . . . ? C16 C15 O1 C1 163.6(2) . . . . ? O1 C1 O2 C17 -51.9(3) . . . . ? C2 C1 O2 C17 -173.7(2) . . . . ? C10 C1 O2 C17 64.2(3) . . . . ? C18 C17 O2 C1 -167.4(2) . . . . ? O5 C13 O4 C8 7.5(6) . . . . ? C14 C13 O4 C8 -173.0(3) . . . . ? C7 C8 O4 C13 -96.1(3) . . . . ? C9 C8 O4 C13 143.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.358 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.044 data_a3 _database_code_depnum_ccdc_archive 'CCDC 879028' #TrackingRef 'web_deposit_cif_file_3_xuesongxu_1335513864.compound 16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 O8 S' _chemical_formula_weight 406.48 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.724(7) _cell_length_b 6.790(3) _cell_length_c 22.394(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.516(9) _cell_angle_gamma 90.00 _cell_volume 2123.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.192 _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 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 40753 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3844 _reflns_number_gt 3066 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker,2003) _computing_cell_refinement SAINT(Bruker,2001) _computing_data_reduction APEX2(Bruker,2003) _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics DIAMOND _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0710P)^2^+1.3247P] 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 0.0078(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3844 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.11781(5) -0.9825(2) -0.23138(4) 0.1082(5) Uani 1 1 d . . . O1 O 0.23337(14) -0.7671(3) -0.28073(9) 0.0684(5) Uani 1 1 d . . . O2 O -0.01297(12) -1.0617(3) -0.20330(8) 0.0687(6) Uani 1 1 d . . . O3 O -0.1519(2) -1.0585(8) -0.29214(12) 0.191(2) Uani 1 1 d . . . O4 O -0.11862(17) -0.7747(6) -0.22430(19) 0.1670(18) Uani 1 1 d . . . O5 O 0.16612(12) -1.2791(2) 0.00264(7) 0.0546(4) Uani 1 1 d . . . O6 O 0.05576(19) -1.1904(4) 0.04599(11) 0.1038(9) Uani 1 1 d . . . O7 O 0.31471(12) -0.9229(3) 0.05308(8) 0.0702(5) Uani 1 1 d . . . O8 O 0.47443(18) -0.8614(6) 0.10669(14) 0.1286(12) Uani 1 1 d . . . C1 C 0.22890(18) -0.7691(4) -0.22723(12) 0.0550(6) Uani 1 1 d . . . C2 C 0.13434(16) -0.8007(4) -0.21524(10) 0.0490(5) Uani 1 1 d . . . H2 H 0.0925 -0.8695 -0.2523 0.059 Uiso 1 1 calc R . . C3 C 0.14771(14) -0.9405(3) -0.15846(9) 0.0395(5) Uani 1 1 d . . . H3 H 0.1663 -1.0673 -0.1720 0.047 Uiso 1 1 calc R . . C4 C 0.05462(14) -0.9815(3) -0.14474(9) 0.0440(5) Uani 1 1 d . . . H4 H 0.0293 -0.8603 -0.1323 0.053 Uiso 1 1 calc R . . C5 C 0.06610(16) -1.1408(3) -0.09511(10) 0.0480(5) Uani 1 1 d . . . H5A H 0.0078 -1.1488 -0.0839 0.058 Uiso 1 1 calc R . . H5B H 0.0754 -1.2668 -0.1127 0.058 Uiso 1 1 calc R . . C6 C 0.15003(15) -1.1017(3) -0.03614(10) 0.0441(5) Uani 1 1 d . . . H6 H 0.1358 -0.9899 -0.0129 0.053 Uiso 1 1 calc R . . C7 C 0.24268(15) -1.0640(3) -0.05121(10) 0.0447(5) Uani 1 1 d . . . H7 H 0.2519 -1.1799 -0.0747 0.054 Uiso 1 1 calc R . . C8 C 0.23075(14) -0.8867(3) -0.09740(10) 0.0416(5) Uani 1 1 d . . . C9 C 0.32310(16) -0.8701(4) -0.11617(12) 0.0574(6) Uani 1 1 d . . . H9A H 0.3749 -0.8252 -0.0799 0.069 Uiso 1 1 calc R . . H9B H 0.3399 -1.0001 -0.1272 0.069 Uiso 1 1 calc R . . C10 C 0.31461(18) -0.7302(4) -0.17126(13) 0.0671(7) Uani 1 1 d . . . H10A H 0.3115 -0.5959 -0.1573 0.080 Uiso 1 1 calc R . . H10B H 0.3718 -0.7420 -0.1837 0.080 Uiso 1 1 calc R . . C11 C 0.08892(19) -0.5965(4) -0.21393(13) 0.0626(7) Uani 1 1 d . . . H11A H 0.0848 -0.5265 -0.2519 0.094 Uiso 1 1 calc R . . H11B H 0.1278 -0.5233 -0.1783 0.094 Uiso 1 1 calc R . . H11C H 0.0259 -0.6128 -0.2107 0.094 Uiso 1 1 calc R . . C12 C -0.1801(2) -1.0852(7) -0.18525(17) 0.1149(16) Uani 1 1 d . . . H12A H -0.2455 -1.0417 -0.2001 0.172 Uiso 1 1 calc R . . H12B H -0.1514 -1.0446 -0.1423 0.172 Uiso 1 1 calc R . . H12C H -0.1781 -1.2262 -0.1878 0.172 Uiso 1 1 calc R . . C13 C 0.1154(2) -1.3038(4) 0.04214(11) 0.0622(7) Uani 1 1 d . . . C14 C 0.1421(3) -1.4896(5) 0.07921(14) 0.0819(9) Uani 1 1 d . . . H14A H 0.1042 -1.5029 0.1068 0.123 Uiso 1 1 calc R . . H14B H 0.2087 -1.4854 0.1036 0.123 Uiso 1 1 calc R . . H14C H 0.1306 -1.5999 0.0510 0.123 Uiso 1 1 calc R . . C15 C 0.32958(17) -1.0587(4) 0.00870(12) 0.0601(6) Uani 1 1 d . . . H15A H 0.3405 -1.1891 0.0273 0.072 Uiso 1 1 calc R . . H15B H 0.3861 -1.0207 -0.0020 0.072 Uiso 1 1 calc R . . C16 C 0.3888(3) -0.9233(7) 0.11040(15) 0.1036(13) Uani 1 1 d . . . H16A H 0.3707 -0.8392 0.1398 0.124 Uiso 1 1 calc R . . H16B H 0.3962 -1.0559 0.1274 0.124 Uiso 1 1 calc R . . C17 C 0.4757(4) -0.6563(11) 0.0939(3) 0.163(2) Uani 1 1 d . . . H17A H 0.5372 -0.6207 0.0909 0.244 Uiso 1 1 calc R . . H17B H 0.4638 -0.5829 0.1273 0.244 Uiso 1 1 calc R . . H17C H 0.4270 -0.6269 0.0548 0.244 Uiso 1 1 calc R . . C18 C 0.21295(18) -0.6925(4) -0.06703(11) 0.0553(6) Uani 1 1 d . . . H18A H 0.2054 -0.5867 -0.0966 0.083 Uiso 1 1 calc R . . H18B H 0.2665 -0.6655 -0.0302 0.083 Uiso 1 1 calc R . . H18C H 0.1559 -0.7046 -0.0553 0.083 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 S1 0.0439(4) 0.1842(12) 0.0737(5) 0.0637(6) -0.0136(3) -0.0333(5) O1 0.0821(13) 0.0671(12) 0.0691(12) 0.0131(9) 0.0425(10) 0.0020(9) O2 0.0507(10) 0.1008(15) 0.0433(9) 0.0041(9) -0.0011(8) -0.0226(9) O3 0.0878(19) 0.395(7) 0.0570(14) 0.032(2) -0.0245(13) -0.073(3) O4 0.0482(13) 0.182(3) 0.244(4) 0.144(3) 0.0081(18) 0.0090(16) O5 0.0635(10) 0.0498(9) 0.0494(9) 0.0094(7) 0.0162(8) 0.0109(7) O6 0.1162(19) 0.124(2) 0.0956(17) 0.0499(15) 0.0682(15) 0.0568(16) O7 0.0540(10) 0.0992(15) 0.0456(9) -0.0133(9) -0.0009(8) 0.0070(10) O8 0.0568(15) 0.192(3) 0.112(2) -0.048(2) -0.0090(13) -0.0010(18) C1 0.0587(14) 0.0514(14) 0.0612(15) 0.0062(11) 0.0277(12) -0.0014(11) C2 0.0457(12) 0.0566(14) 0.0430(11) 0.0001(10) 0.0117(10) -0.0061(10) C3 0.0381(10) 0.0416(11) 0.0387(10) -0.0051(9) 0.0121(9) -0.0001(8) C4 0.0369(11) 0.0547(13) 0.0361(10) -0.0004(9) 0.0057(9) -0.0020(9) C5 0.0435(11) 0.0514(13) 0.0468(12) 0.0033(10) 0.0110(9) -0.0033(10) C6 0.0477(12) 0.0412(12) 0.0404(11) 0.0022(9) 0.0097(9) 0.0070(9) C7 0.0408(11) 0.0457(12) 0.0444(11) -0.0047(9) 0.0090(9) 0.0077(9) C8 0.0355(10) 0.0423(12) 0.0437(11) -0.0066(9) 0.0078(9) 0.0008(8) C9 0.0377(11) 0.0673(16) 0.0650(15) -0.0033(12) 0.0134(11) -0.0026(11) C10 0.0496(14) 0.0780(19) 0.0787(18) 0.0034(15) 0.0275(13) -0.0111(13) C11 0.0545(14) 0.0623(16) 0.0694(16) 0.0182(13) 0.0172(12) 0.0070(12) C12 0.0540(17) 0.185(4) 0.092(2) 0.046(3) 0.0036(16) -0.039(2) C13 0.0639(15) 0.0748(18) 0.0452(13) 0.0119(12) 0.0134(12) 0.0075(14) C14 0.096(2) 0.082(2) 0.0638(17) 0.0265(16) 0.0205(17) 0.0067(17) C15 0.0456(13) 0.0722(17) 0.0542(14) 0.0015(12) 0.0041(11) 0.0113(12) C16 0.083(2) 0.147(4) 0.0561(18) -0.011(2) -0.0134(16) 0.003(2) C17 0.121(4) 0.197(6) 0.152(5) -0.045(5) 0.016(3) -0.064(4) C18 0.0599(14) 0.0461(13) 0.0521(13) -0.0104(11) 0.0069(11) 0.0019(11) _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 S1 O3 1.391(4) . ? S1 O4 1.420(4) . ? S1 O2 1.566(2) . ? S1 C12 1.731(3) . ? O1 C1 1.221(3) . ? O2 C4 1.476(3) . ? O5 C13 1.338(3) . ? O5 C6 1.459(3) . ? O6 C13 1.191(3) . ? O7 C16 1.396(3) . ? O7 C15 1.423(3) . ? O8 C16 1.357(5) . ? O8 C17 1.423(7) . ? C1 C10 1.493(4) . ? C1 C2 1.515(3) . ? C2 C11 1.544(4) . ? C2 C3 1.548(3) . ? C2 H2 0.9800 . ? C3 C4 1.523(3) . ? C3 C8 1.561(3) . ? C3 H3 0.9800 . ? C4 C5 1.521(3) . ? C4 H4 0.9800 . ? C5 C6 1.518(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(3) . ? C6 H6 0.9800 . ? C7 C15 1.532(3) . ? C7 C8 1.560(3) . ? C7 H7 0.9800 . ? C8 C18 1.544(3) . ? C8 C9 1.550(3) . ? C9 C10 1.530(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.493(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O4 117.7(3) . . ? O3 S1 O2 105.6(2) . . ? O4 S1 O2 109.79(13) . . ? O3 S1 C12 109.9(2) . . ? O4 S1 C12 108.0(3) . . ? O2 S1 C12 105.31(15) . . ? C4 O2 S1 122.06(18) . . ? C13 O5 C6 118.53(19) . . ? C16 O7 C15 113.1(2) . . ? C16 O8 C17 112.8(4) . . ? O1 C1 C10 121.8(2) . . ? O1 C1 C2 121.0(2) . . ? C10 C1 C2 117.1(2) . . ? C1 C2 C11 107.72(19) . . ? C1 C2 C3 110.37(18) . . ? C11 C2 C3 118.53(19) . . ? C1 C2 H2 106.5 . . ? C11 C2 H2 106.5 . . ? C3 C2 H2 106.5 . . ? C4 C3 C2 112.96(17) . . ? C4 C3 C8 111.78(16) . . ? C2 C3 C8 115.85(17) . . ? C4 C3 H3 105.0 . . ? C2 C3 H3 105.0 . . ? C8 C3 H3 105.0 . . ? O2 C4 C5 105.92(18) . . ? O2 C4 C3 106.51(16) . . ? C5 C4 C3 112.29(18) . . ? O2 C4 H4 110.6 . . ? C5 C4 H4 110.6 . . ? C3 C4 H4 110.6 . . ? C6 C5 C4 112.46(18) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? O5 C6 C5 107.87(18) . . ? O5 C6 C7 106.39(16) . . ? C5 C6 C7 112.00(18) . . ? O5 C6 H6 110.2 . . ? C5 C6 H6 110.2 . . ? C7 C6 H6 110.2 . . ? C6 C7 C15 111.49(19) . . ? C6 C7 C8 110.82(16) . . ? C15 C7 C8 116.71(19) . . ? C6 C7 H7 105.6 . . ? C15 C7 H7 105.6 . . ? C8 C7 H7 105.6 . . ? C18 C8 C9 110.11(19) . . ? C18 C8 C7 111.47(18) . . ? C9 C8 C7 108.18(17) . . ? C18 C8 C3 112.99(17) . . ? C9 C8 C3 106.87(17) . . ? C7 C8 C3 106.99(17) . . ? C10 C9 C8 114.2(2) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C1 C10 C9 113.4(2) . . ? C1 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C1 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S1 C12 H12A 109.5 . . ? S1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? S1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O6 C13 O5 123.1(2) . . ? O6 C13 C14 125.2(3) . . ? O5 C13 C14 111.7(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O7 C15 C7 110.83(19) . . ? O7 C15 H15A 109.5 . . ? C7 C15 H15A 109.5 . . ? O7 C15 H15B 109.5 . . ? C7 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O8 C16 O7 114.4(3) . . ? O8 C16 H16A 108.7 . . ? O7 C16 H16A 108.7 . . ? O8 C16 H16B 108.7 . . ? O7 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? O8 C17 H17A 109.5 . . ? O8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 O3 S1 O2 C4 167.0(2) . . . . ? O4 S1 O2 C4 39.2(3) . . . . ? C12 S1 O2 C4 -76.8(2) . . . . ? O1 C1 C2 C11 -90.7(3) . . . . ? C10 C1 C2 C11 86.1(3) . . . . ? O1 C1 C2 C3 138.5(2) . . . . ? C10 C1 C2 C3 -44.7(3) . . . . ? C1 C2 C3 C4 -178.87(18) . . . . ? C11 C2 C3 C4 56.3(3) . . . . ? C1 C2 C3 C8 50.4(2) . . . . ? C11 C2 C3 C8 -74.5(2) . . . . ? S1 O2 C4 C5 108.50(19) . . . . ? S1 O2 C4 C3 -131.78(17) . . . . ? C2 C3 C4 O2 56.4(2) . . . . ? C8 C3 C4 O2 -170.85(17) . . . . ? C2 C3 C4 C5 171.88(18) . . . . ? C8 C3 C4 C5 -55.3(2) . . . . ? O2 C4 C5 C6 166.92(18) . . . . ? C3 C4 C5 C6 51.1(2) . . . . ? C13 O5 C6 C5 -85.6(2) . . . . ? C13 O5 C6 C7 154.1(2) . . . . ? C4 C5 C6 O5 -169.05(17) . . . . ? C4 C5 C6 C7 -52.3(2) . . . . ? O5 C6 C7 C15 -52.9(2) . . . . ? C5 C6 C7 C15 -170.57(19) . . . . ? O5 C6 C7 C8 175.25(16) . . . . ? C5 C6 C7 C8 57.6(2) . . . . ? C6 C7 C8 C18 64.6(2) . . . . ? C15 C7 C8 C18 -64.4(2) . . . . ? C6 C7 C8 C9 -174.17(18) . . . . ? C15 C7 C8 C9 56.8(2) . . . . ? C6 C7 C8 C3 -59.4(2) . . . . ? C15 C7 C8 C3 171.58(18) . . . . ? C4 C3 C8 C18 -64.6(2) . . . . ? C2 C3 C8 C18 66.8(2) . . . . ? C4 C3 C8 C9 174.18(19) . . . . ? C2 C3 C8 C9 -54.5(2) . . . . ? C4 C3 C8 C7 58.5(2) . . . . ? C2 C3 C8 C7 -170.20(16) . . . . ? C18 C8 C9 C10 -69.7(3) . . . . ? C7 C8 C9 C10 168.3(2) . . . . ? C3 C8 C9 C10 53.4(3) . . . . ? O1 C1 C10 C9 -137.3(2) . . . . ? C2 C1 C10 C9 45.9(3) . . . . ? C8 C9 C10 C1 -50.8(3) . . . . ? C6 O5 C13 O6 2.1(4) . . . . ? C6 O5 C13 C14 -178.6(2) . . . . ? C16 O7 C15 C7 175.4(3) . . . . ? C6 C7 C15 O7 -53.1(3) . . . . ? C8 C7 C15 O7 75.6(3) . . . . ? C17 O8 C16 O7 69.7(5) . . . . ? C15 O7 C16 O8 64.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.314 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.045 data_a4 _database_code_depnum_ccdc_archive 'CCDC 879029' #TrackingRef 'web_deposit_cif_file_4_xuesongxu_1335513864.compound 22.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H36 O3 Si' _chemical_formula_weight 352.58 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 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 11.6292(15) _cell_length_b 7.7435(11) _cell_length_c 12.2967(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.516(3) _cell_angle_gamma 90.00 _cell_volume 1107.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.057 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9212 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8522 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3770 _reflns_number_gt 3429 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker,2003) _computing_cell_refinement SAINT(Bruker,2001) _computing_data_reduction APEX2(Bruker,2003) _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics DIAMOND _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0707P)^2^+0.0143P] 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 0.04(13) _refine_ls_number_reflns 3770 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.78936(5) 0.25033(7) 0.95683(4) 0.03422(17) Uani 1 1 d . . . O1 O 0.92149(17) 0.1552(2) 1.44619(14) 0.0540(5) Uani 1 1 d . . . H1A H 0.9286 0.1948 1.5086 0.081 Uiso 1 1 calc R . . O2 O 0.9295(2) 0.3859(3) 1.60809(15) 0.0688(6) Uani 1 1 d . . . H2A H 0.9706 0.4681 1.5893 0.103 Uiso 1 1 calc R . . O3 O 0.75809(12) 0.2565(2) 1.08707(11) 0.0393(3) Uani 1 1 d . . . C1 C 0.8986(2) 0.2943(3) 1.37105(18) 0.0402(5) Uani 1 1 d . . . C2 C 0.8290(2) 0.4354(3) 1.43403(19) 0.0450(6) Uani 1 1 d . . . H2B H 0.8678 0.5480 1.4241 0.054 Uiso 1 1 calc R . . C3 C 0.7103(2) 0.4422(4) 1.3749(2) 0.0486(6) Uani 1 1 d . . . C4 C 0.7240(3) 0.5631(3) 1.2790(2) 0.0532(7) Uani 1 1 d . . . H4A H 0.6930 0.6749 1.2835 0.064 Uiso 1 1 calc R . . C5 C 0.7779(2) 0.5170(3) 1.1890(2) 0.0463(6) Uani 1 1 d . . . H5A H 0.7884 0.5993 1.1338 0.056 Uiso 1 1 calc R . . C6 C 0.82253(19) 0.3377(3) 1.17310(16) 0.0354(5) Uani 1 1 d . . . H6A H 0.9041 0.3448 1.1511 0.043 Uiso 1 1 calc R . . C7 C 0.81502(19) 0.2260(3) 1.27815(17) 0.0364(5) Uani 1 1 d . . . C8 C 0.69711(19) 0.2554(4) 1.33278(17) 0.0439(5) Uani 1 1 d . . . H8A H 0.6942 0.1790 1.3972 0.053 Uiso 1 1 calc R . . C9 C 1.0140(2) 0.3618(4) 1.3312(2) 0.0519(6) Uani 1 1 d . . . H9A H 1.0595 0.4014 1.3928 0.078 Uiso 1 1 calc R . . H9B H 1.0012 0.4569 1.2813 0.078 Uiso 1 1 calc R . . H9C H 1.0546 0.2698 1.2943 0.078 Uiso 1 1 calc R . . C10 C 0.8197(3) 0.3999(5) 1.5564(2) 0.0629(8) Uani 1 1 d . . . H10A H 0.7764 0.4937 1.5905 0.075 Uiso 1 1 calc R . . H10B H 0.7769 0.2924 1.5674 0.075 Uiso 1 1 calc R . . C11 C 0.6093(3) 0.5016(6) 1.4450(3) 0.0814(11) Uani 1 1 d . . . H11A H 0.5394 0.5018 1.4015 0.122 Uiso 1 1 calc R . . H11B H 0.6243 0.6173 1.4719 0.122 Uiso 1 1 calc R . . H11C H 0.6005 0.4233 1.5059 0.122 Uiso 1 1 calc R . . C12 C 0.9391(3) 0.1697(5) 0.9375(3) 0.0678(9) Uani 1 1 d . . . H12A H 0.9932 0.2511 0.9693 0.102 Uiso 1 1 calc R . . H12B H 0.9542 0.1579 0.8604 0.102 Uiso 1 1 calc R . . H12C H 0.9478 0.0583 0.9727 0.102 Uiso 1 1 calc R . . C13 C 0.7808(3) 0.4682(3) 0.8936(2) 0.0601(8) Uani 1 1 d . . . H13A H 0.8391 0.5425 0.9257 0.090 Uiso 1 1 calc R . . H13B H 0.7054 0.5173 0.9062 0.090 Uiso 1 1 calc R . . H13C H 0.7935 0.4586 0.8160 0.090 Uiso 1 1 calc R . . C14 C 0.6778(2) 0.1011(3) 0.8968(2) 0.0446(6) Uani 1 1 d . . . C15 C 0.6874(3) 0.0979(6) 0.7723(2) 0.0816(12) Uani 1 1 d . . . H15A H 0.6297 0.0206 0.7422 0.122 Uiso 1 1 calc R . . H15B H 0.7633 0.0578 0.7522 0.122 Uiso 1 1 calc R . . H15C H 0.6753 0.2134 0.7438 0.122 Uiso 1 1 calc R . . C16 C 0.5583(2) 0.1622(5) 0.9264(3) 0.0724(9) Uani 1 1 d . . . H16A H 0.5015 0.0841 0.8955 0.109 Uiso 1 1 calc R . . H16B H 0.5459 0.2775 0.8978 0.109 Uiso 1 1 calc R . . H16C H 0.5508 0.1641 1.0049 0.109 Uiso 1 1 calc R . . C17 C 0.6947(3) -0.0811(4) 0.9403(3) 0.0864(12) Uani 1 1 d . . . H17A H 0.6367 -0.1567 0.9091 0.130 Uiso 1 1 calc R . . H17B H 0.6878 -0.0805 1.0188 0.130 Uiso 1 1 calc R . . H17C H 0.7705 -0.1224 0.9207 0.130 Uiso 1 1 calc R . . C18 C 0.8374(3) 0.0374(3) 1.2495(2) 0.0512(6) Uani 1 1 d . . . H18A H 0.7843 0.0013 1.1926 0.077 Uiso 1 1 calc R . . H18B H 0.8265 -0.0339 1.3134 0.077 Uiso 1 1 calc R . . H18C H 0.9157 0.0247 1.2242 0.077 Uiso 1 1 calc R . . C19 C 0.5916(2) 0.2199(4) 1.2662(2) 0.0570(8) Uani 1 1 d . . . H19A H 0.5754 0.2940 1.2075 0.068 Uiso 1 1 calc R . . C20 C 0.5202(3) 0.0923(6) 1.2844(3) 0.0854(12) Uani 1 1 d . . . H20C H 0.5339 0.0159 1.3425 0.102 Uiso 1 1 calc R . . H20A H 0.4552 0.0772 1.2393 0.102 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 0.0390(3) 0.0342(3) 0.0294(3) -0.0012(3) -0.0024(2) 0.0023(3) O1 0.0727(13) 0.0581(11) 0.0308(9) 0.0116(8) -0.0157(9) -0.0018(9) O2 0.0868(14) 0.0848(15) 0.0346(10) 0.0013(10) -0.0179(10) -0.0206(12) O3 0.0449(8) 0.0457(8) 0.0273(7) -0.0001(8) -0.0042(6) -0.0068(8) C1 0.0476(13) 0.0428(13) 0.0301(11) 0.0057(9) -0.0055(10) -0.0047(9) C2 0.0541(14) 0.0522(13) 0.0286(12) -0.0039(10) -0.0027(11) -0.0084(11) C3 0.0503(15) 0.0616(16) 0.0339(13) -0.0106(11) 0.0033(11) -0.0007(11) C4 0.0663(17) 0.0440(13) 0.0491(16) -0.0086(12) -0.0100(13) 0.0081(12) C5 0.0623(16) 0.0387(12) 0.0378(13) 0.0055(10) -0.0082(12) -0.0039(11) C6 0.0406(12) 0.0388(11) 0.0269(11) 0.0004(9) -0.0015(9) -0.0080(9) C7 0.0435(11) 0.0382(12) 0.0275(10) 0.0034(9) -0.0027(9) -0.0077(9) C8 0.0448(12) 0.0564(13) 0.0306(11) 0.0037(13) 0.0005(9) -0.0110(13) C9 0.0441(13) 0.0696(17) 0.0419(14) -0.0042(12) -0.0058(11) -0.0091(12) C10 0.075(2) 0.082(2) 0.0318(14) -0.0052(14) -0.0003(14) -0.0138(16) C11 0.0591(19) 0.123(3) 0.062(2) -0.029(2) 0.0097(16) 0.0121(19) C12 0.0507(16) 0.0767(19) 0.076(2) -0.0252(17) 0.0031(15) 0.0113(14) C13 0.090(2) 0.0461(15) 0.0442(16) 0.0096(11) -0.0168(15) -0.0120(13) C14 0.0539(14) 0.0438(13) 0.0359(13) -0.0040(10) -0.0038(11) -0.0047(11) C15 0.079(2) 0.125(3) 0.0409(16) -0.0307(19) -0.0043(16) -0.023(2) C16 0.0460(16) 0.091(2) 0.080(2) -0.0223(19) -0.0085(15) -0.0110(14) C17 0.106(3) 0.0379(16) 0.115(3) -0.0017(17) -0.033(2) -0.0150(16) C18 0.0692(17) 0.0378(13) 0.0463(14) 0.0031(10) -0.0153(13) -0.0023(11) C19 0.0434(12) 0.087(2) 0.0407(13) -0.0046(14) 0.0014(11) -0.0152(14) C20 0.062(2) 0.128(3) 0.065(2) 0.004(2) -0.0041(17) -0.047(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 O3 1.6462(14) . ? Si1 C13 1.860(3) . ? Si1 C12 1.868(3) . ? Si1 C14 1.883(3) . ? O1 C1 1.442(3) . ? O1 H1A 0.8300 . ? O2 C10 1.425(4) . ? O2 H2A 0.8300 . ? O3 C6 1.436(3) . ? C1 C9 1.525(3) . ? C1 C2 1.568(3) . ? C1 C7 1.584(3) . ? C2 C10 1.534(3) . ? C2 C3 1.555(4) . ? C2 H2B 0.9900 . ? C3 C4 1.514(4) . ? C3 C11 1.534(4) . ? C3 C8 1.543(4) . ? C4 C5 1.326(4) . ? C4 H4A 0.9400 . ? C5 C6 1.496(3) . ? C5 H5A 0.9400 . ? C6 C7 1.558(3) . ? C6 H6A 0.9900 . ? C7 C18 1.525(3) . ? C7 C8 1.549(3) . ? C8 C19 1.494(3) . ? C8 H8A 0.9900 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C14 C16 1.515(4) . ? C14 C17 1.521(4) . ? C14 C15 1.537(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 H16C 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 C20 1.312(5) . ? C19 H19A 0.9400 . ? C20 H20C 0.9400 . ? C20 H20A 0.9400 . ? 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 O3 Si1 C13 111.65(12) . . ? O3 Si1 C12 110.37(13) . . ? C13 Si1 C12 107.24(16) . . ? O3 Si1 C14 103.97(10) . . ? C13 Si1 C14 111.04(12) . . ? C12 Si1 C14 112.66(13) . . ? C1 O1 H1A 109.5 . . ? C10 O2 H2A 109.5 . . ? C6 O3 Si1 127.67(13) . . ? O1 C1 C9 107.7(2) . . ? O1 C1 C2 107.27(18) . . ? C9 C1 C2 112.29(19) . . ? O1 C1 C7 108.73(17) . . ? C9 C1 C7 114.76(19) . . ? C2 C1 C7 105.85(19) . . ? C10 C2 C3 113.2(2) . . ? C10 C2 C1 113.7(2) . . ? C3 C2 C1 104.60(18) . . ? C10 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? C4 C3 C11 109.8(3) . . ? C4 C3 C8 109.2(2) . . ? C11 C3 C8 113.3(2) . . ? C4 C3 C2 106.6(2) . . ? C11 C3 C2 115.3(2) . . ? C8 C3 C2 102.2(2) . . ? C5 C4 C3 122.5(2) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? O3 C6 C5 108.9(2) . . ? O3 C6 C7 109.58(17) . . ? C5 C6 C7 112.64(19) . . ? O3 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C18 C7 C8 113.2(2) . . ? C18 C7 C6 109.21(19) . . ? C8 C7 C6 109.53(19) . . ? C18 C7 C1 112.4(2) . . ? C8 C7 C1 100.24(17) . . ? C6 C7 C1 111.96(17) . . ? C19 C8 C3 115.8(2) . . ? C19 C8 C7 117.46(19) . . ? C3 C8 C7 101.37(19) . . ? C19 C8 H8A 107.2 . . ? C3 C8 H8A 107.2 . . ? C7 C8 H8A 107.2 . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C2 112.3(2) . . ? O2 C10 H10A 109.1 . . ? C2 C10 H10A 109.1 . . ? O2 C10 H10B 109.1 . . ? C2 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si1 C13 H13A 109.5 . . ? Si1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C17 108.8(3) . . ? C16 C14 C15 108.6(3) . . ? C17 C14 C15 109.0(3) . . ? C16 C14 Si1 110.16(19) . . ? C17 C14 Si1 110.2(2) . . ? C15 C14 Si1 110.11(19) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 C18 H18A 109.5 . . ? C7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C8 124.3(3) . . ? C20 C19 H19A 117.9 . . ? C8 C19 H19A 117.9 . . ? C19 C20 H20C 120.0 . . ? C19 C20 H20A 120.0 . . ? H20C C20 H20A 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 C13 Si1 O3 C6 -66.9(2) . . . . ? C12 Si1 O3 C6 52.3(2) . . . . ? C14 Si1 O3 C6 173.35(18) . . . . ? O1 C1 C2 C10 7.8(3) . . . . ? C9 C1 C2 C10 -110.3(2) . . . . ? C7 C1 C2 C10 123.8(2) . . . . ? O1 C1 C2 C3 -116.2(2) . . . . ? C9 C1 C2 C3 125.7(2) . . . . ? C7 C1 C2 C3 -0.3(2) . . . . ? C10 C2 C3 C4 150.9(2) . . . . ? C1 C2 C3 C4 -84.8(2) . . . . ? C10 C2 C3 C11 28.8(4) . . . . ? C1 C2 C3 C11 153.1(3) . . . . ? C10 C2 C3 C8 -94.5(2) . . . . ? C1 C2 C3 C8 29.8(2) . . . . ? C11 C3 C4 C5 -158.5(3) . . . . ? C8 C3 C4 C5 -33.8(4) . . . . ? C2 C3 C4 C5 75.9(3) . . . . ? C3 C4 C5 C6 4.1(4) . . . . ? Si1 O3 C6 C5 92.8(2) . . . . ? Si1 O3 C6 C7 -143.62(16) . . . . ? C4 C5 C6 O3 113.0(3) . . . . ? C4 C5 C6 C7 -8.7(3) . . . . ? O3 C6 C7 C18 46.7(2) . . . . ? C5 C6 C7 C18 168.0(2) . . . . ? O3 C6 C7 C8 -77.9(2) . . . . ? C5 C6 C7 C8 43.5(3) . . . . ? O3 C6 C7 C1 171.84(17) . . . . ? C5 C6 C7 C1 -66.8(2) . . . . ? O1 C1 C7 C18 -34.6(3) . . . . ? C9 C1 C7 C18 86.0(2) . . . . ? C2 C1 C7 C18 -149.59(19) . . . . ? O1 C1 C7 C8 85.9(2) . . . . ? C9 C1 C7 C8 -153.4(2) . . . . ? C2 C1 C7 C8 -29.0(2) . . . . ? O1 C1 C7 C6 -158.01(18) . . . . ? C9 C1 C7 C6 -37.4(3) . . . . ? C2 C1 C7 C6 87.0(2) . . . . ? C4 C3 C8 C19 -64.6(3) . . . . ? C11 C3 C8 C19 58.1(3) . . . . ? C2 C3 C8 C19 -177.27(18) . . . . ? C4 C3 C8 C7 63.7(2) . . . . ? C11 C3 C8 C7 -173.7(2) . . . . ? C2 C3 C8 C7 -49.0(2) . . . . ? C18 C7 C8 C19 -65.1(3) . . . . ? C6 C7 C8 C19 57.1(3) . . . . ? C1 C7 C8 C19 174.9(2) . . . . ? C18 C7 C8 C3 167.7(2) . . . . ? C6 C7 C8 C3 -70.1(2) . . . . ? C1 C7 C8 C3 47.8(2) . . . . ? C3 C2 C10 O2 177.2(2) . . . . ? C1 C2 C10 O2 58.0(3) . . . . ? O3 Si1 C14 C16 53.9(2) . . . . ? C13 Si1 C14 C16 -66.3(2) . . . . ? C12 Si1 C14 C16 173.4(2) . . . . ? O3 Si1 C14 C17 -66.1(2) . . . . ? C13 Si1 C14 C17 173.7(2) . . . . ? C12 Si1 C14 C17 53.4(3) . . . . ? O3 Si1 C14 C15 173.7(2) . . . . ? C13 Si1 C14 C15 53.5(3) . . . . ? C12 Si1 C14 C15 -66.8(3) . . . . ? C3 C8 C19 C20 -128.7(3) . . . . ? C7 C8 C19 C20 111.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.214 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.040