# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1556 data_k114 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_contact_author_name 'Patrick Perlmutter' _publ_contact_author_address ; Department of Chemistry Monash University Clayton Victoria Australia 3800 ; _publ_requested_journal ? _publ_section_title ; The vitamin C route to the ciguatoxins. The enantioselective synthesis of a ring F building block. ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 O6 Si' _chemical_formula_weight 382.52 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' 'Si' 'Si' 0.0817 0.0704 '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 6.51700(10) _cell_length_b 11.5188(4) _cell_length_c 26.6955(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2003.98(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 CCD _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23642 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.1164 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5687 _reflns_number_gt 3269 _reflns_threshold_expression >2sigma(I) _computing_data_collection ' Collect (Nonius, 1998) ' _computing_cell_refinement ' Denzo-SMN (Otwinowski and Major, 1997) ' _computing_data_reduction ' Denzo-SMN (Otwinowski and Major, 1997) ' _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^)+(0.0387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.16(13) _refine_ls_number_reflns 5687 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1340 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'Fourier difference' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.86928(9) 0.09089(6) 0.23767(2) 0.02789(16) Uani 1 d . . . O1 O 0.90524(18) 0.11768(12) 0.17703(5) 0.0254(4) Uani 1 d . . . O2 O 1.1514(2) 0.06944(13) 0.05938(6) 0.0351(4) Uani 1 d . . . H2 H 1.1277 0.0802 0.0274 0.046(7) Uiso 1 d R . . O3 O 1.1503(2) 0.27727(12) 0.11951(6) 0.0298(4) Uani 1 d . . . O4 O 1.3758(2) 0.19236(15) 0.17040(6) 0.0423(4) Uani 1 d . . . O5 O 0.57512(19) 0.40322(12) 0.04160(5) 0.0274(4) Uani 1 d . . . O6 O 0.8298(2) 0.42724(12) 0.09743(6) 0.0290(4) Uani 1 d . . . C1 C 1.0647(3) 0.0876(2) 0.14344(8) 0.0257(5) Uani 1 d . . . C2 C 1.1406(4) -0.03523(18) 0.14916(9) 0.0346(6) Uani 1 d . . . H2A H 1.1682 -0.0520 0.1849 0.041 Uiso 1 calc R . . H2B H 1.2699 -0.0455 0.1302 0.041 Uiso 1 calc R . . C3 C 0.9790(4) -0.1173(2) 0.12945(10) 0.0430(7) Uani 1 d . . . H3 H 0.9868 -0.1966 0.1390 0.052 Uiso 1 calc R . . C4 C 0.8261(4) -0.0849(2) 0.09938(10) 0.0427(6) Uani 1 d . . . H4 H 0.7322 -0.1429 0.0886 0.051 Uiso 1 calc R . . C5 C 0.7923(3) 0.03812(18) 0.08129(9) 0.0323(6) Uani 1 d . . . H5A H 0.6761 0.0736 0.0996 0.039 Uiso 1 calc R . . H5B H 0.7584 0.0378 0.0451 0.039 Uiso 1 calc R . . C6 C 0.9857(3) 0.10818(19) 0.09012(8) 0.0250(5) Uani 1 d . . . C7 C 0.9823(3) 0.24201(19) 0.08667(8) 0.0253(5) Uani 1 d . . . H7 H 1.0204 0.2640 0.0516 0.030 Uiso 1 calc R . . C8 C 1.2193(3) 0.1864(2) 0.14716(8) 0.0293(5) Uani 1 d . . . C9 C 0.7870(3) 0.30532(18) 0.09978(9) 0.0238(5) Uani 1 d . . . H9 H 0.7353 0.2822 0.1336 0.029 Uiso 1 calc R . . C10 C 0.6209(3) 0.28912(18) 0.05914(8) 0.0272(5) Uani 1 d . . . H10A H 0.6730 0.2400 0.0315 0.033 Uiso 1 calc R . . H10B H 0.4970 0.2521 0.0735 0.033 Uiso 1 calc R . . C11 C 0.6527(3) 0.48338(18) 0.07882(8) 0.0251(5) Uani 1 d . . . C12 C 0.7138(3) 0.59470(19) 0.05338(9) 0.0324(5) Uani 1 d . . . H12A H 0.8045 0.5766 0.0247 0.039 Uiso 1 calc R . . H12B H 0.7925 0.6432 0.0772 0.039 Uiso 1 calc R . . C13 C 0.5287(4) 0.6633(2) 0.03466(9) 0.0372(6) Uani 1 d . . . H13A H 0.5753 0.7396 0.0220 0.045 Uiso 1 calc R . . H13B H 0.4641 0.6210 0.0065 0.045 Uiso 1 calc R . . C14 C 0.3703(4) 0.6820(2) 0.07585(9) 0.0395(6) Uani 1 d . . . H14A H 0.4290 0.7327 0.1022 0.047 Uiso 1 calc R . . H14B H 0.2484 0.7215 0.0617 0.047 Uiso 1 calc R . . C15 C 0.3063(3) 0.5670(2) 0.09882(10) 0.0369(6) Uani 1 d . . . H15A H 0.2369 0.5190 0.0732 0.044 Uiso 1 calc R . . H15B H 0.2078 0.5813 0.1264 0.044 Uiso 1 calc R . . C16 C 0.4928(3) 0.5020(2) 0.11906(8) 0.0284(5) Uani 1 d . . . H16A H 0.5540 0.5468 0.1470 0.034 Uiso 1 calc R . . H16B H 0.4486 0.4258 0.1324 0.034 Uiso 1 calc R . . C17 C 1.1138(4) 0.0844(2) 0.27309(8) 0.0462(7) Uani 1 d . . . H17A H 1.1892 0.0141 0.2636 0.069 Uiso 1 calc R . . H17B H 1.0845 0.0827 0.3091 0.069 Uiso 1 calc R . . H17C H 1.1969 0.1529 0.2652 0.069 Uiso 1 calc R . . C18 C 0.7190(4) 0.2164(2) 0.25999(10) 0.0413(6) Uani 1 d . . . H18A H 0.8005 0.2874 0.2562 0.062 Uiso 1 calc R . . H18B H 0.6839 0.2053 0.2954 0.062 Uiso 1 calc R . . H18C H 0.5929 0.2231 0.2402 0.062 Uiso 1 calc R . . C19 C 0.7240(4) -0.0456(2) 0.24426(11) 0.0544(8) Uani 1 d . . . H19A H 0.5893 -0.0371 0.2284 0.082 Uiso 1 calc R . . H19B H 0.7060 -0.0635 0.2799 0.082 Uiso 1 calc R . . H19C H 0.7996 -0.1088 0.2280 0.082 Uiso 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 0.0312(3) 0.0324(3) 0.0200(3) 0.0011(3) 0.0023(3) 0.0001(3) O1 0.0253(8) 0.0285(8) 0.0224(8) 0.0024(7) 0.0036(6) 0.0013(6) O2 0.0406(9) 0.0444(10) 0.0201(9) -0.0002(7) 0.0038(7) 0.0131(9) O3 0.0230(7) 0.0298(8) 0.0365(9) 0.0044(7) -0.0041(7) -0.0040(7) O4 0.0291(9) 0.0567(11) 0.0410(10) 0.0098(9) -0.0094(8) -0.0049(9) O5 0.0361(9) 0.0249(8) 0.0212(8) 0.0000(7) -0.0045(6) 0.0004(7) O6 0.0229(8) 0.0255(8) 0.0387(9) 0.0023(7) -0.0057(6) -0.0013(7) C1 0.0257(11) 0.0309(13) 0.0206(12) 0.0008(11) 0.0024(9) 0.0022(10) C2 0.0410(13) 0.0364(14) 0.0262(13) 0.0018(11) 0.0021(12) 0.0090(13) C3 0.0662(17) 0.0231(14) 0.0399(16) 0.0004(12) 0.0078(14) 0.0046(13) C4 0.0550(16) 0.0284(13) 0.0447(16) -0.0040(13) 0.0006(13) -0.0063(14) C5 0.0416(13) 0.0290(13) 0.0262(13) -0.0014(10) -0.0040(10) -0.0006(11) C6 0.0260(11) 0.0295(13) 0.0195(12) -0.0022(10) 0.0022(9) 0.0020(10) C7 0.0254(12) 0.0313(13) 0.0193(12) 0.0022(10) -0.0003(10) -0.0017(10) C8 0.0268(12) 0.0400(15) 0.0210(12) 0.0018(11) 0.0022(10) 0.0022(11) C9 0.0238(11) 0.0226(12) 0.0249(13) 0.0002(10) 0.0003(9) -0.0024(10) C10 0.0278(11) 0.0257(12) 0.0280(13) 0.0009(10) -0.0011(11) -0.0020(11) C11 0.0250(11) 0.0274(12) 0.0228(12) 0.0000(10) -0.0033(10) -0.0004(10) C12 0.0355(12) 0.0282(12) 0.0334(14) 0.0016(12) 0.0062(10) -0.0013(11) C13 0.0518(15) 0.0281(13) 0.0319(15) 0.0026(11) -0.0006(12) 0.0017(12) C14 0.0392(13) 0.0373(14) 0.0420(15) -0.0023(12) -0.0052(13) 0.0134(13) C15 0.0273(12) 0.0423(15) 0.0409(15) -0.0041(13) 0.0013(10) 0.0029(12) C16 0.0293(12) 0.0327(13) 0.0230(12) -0.0004(10) 0.0008(10) -0.0037(11) C17 0.0420(14) 0.0695(18) 0.0271(14) 0.0001(13) -0.0025(11) 0.0096(15) C18 0.0417(14) 0.0508(17) 0.0313(14) -0.0082(13) -0.0011(12) 0.0061(12) C19 0.0702(19) 0.0508(18) 0.0422(17) 0.0045(14) 0.0180(15) -0.0156(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 O1 1.6647(15) . ? Si1 C19 1.844(2) . ? Si1 C18 1.845(2) . ? Si1 C17 1.854(2) . ? O1 C1 1.415(2) . ? O2 C6 1.428(2) . ? O3 C8 1.357(3) . ? O3 C7 1.460(2) . ? O4 C8 1.196(2) . ? O5 C10 1.427(2) . ? O5 C11 1.447(2) . ? O6 C11 1.413(2) . ? O6 C9 1.433(2) . ? C1 C2 1.507(3) . ? C1 C8 1.523(3) . ? C1 C6 1.532(3) . ? C2 C3 1.510(3) . ? C3 C4 1.333(3) . ? C4 C5 1.513(3) . ? C5 C6 1.515(3) . ? C6 C7 1.545(3) . ? C7 C9 1.508(3) . ? C9 C10 1.544(3) . ? C11 C12 1.505(3) . ? C11 C16 1.512(3) . ? C12 C13 1.526(3) . ? C13 C14 1.524(3) . ? C14 C15 1.518(3) . ? C15 C16 1.527(3) . ? 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 Si1 C19 108.85(11) . . ? O1 Si1 C18 104.10(10) . . ? C19 Si1 C18 111.40(12) . . ? O1 Si1 C17 112.48(9) . . ? C19 Si1 C17 110.99(13) . . ? C18 Si1 C17 108.85(12) . . ? C1 O1 Si1 132.38(12) . . ? C8 O3 C7 111.12(16) . . ? C10 O5 C11 106.82(15) . . ? C11 O6 C9 107.75(14) . . ? O1 C1 C2 113.98(17) . . ? O1 C1 C8 105.17(17) . . ? C2 C1 C8 118.54(17) . . ? O1 C1 C6 107.71(15) . . ? C2 C1 C6 110.45(18) . . ? C8 C1 C6 99.65(17) . . ? C1 C2 C3 108.91(18) . . ? C4 C3 C2 123.8(2) . . ? C3 C4 C5 124.3(2) . . ? C4 C5 C6 109.16(18) . . ? O2 C6 C5 111.91(17) . . ? O2 C6 C1 103.40(15) . . ? C5 C6 C1 109.99(18) . . ? O2 C6 C7 106.77(16) . . ? C5 C6 C7 120.68(18) . . ? C1 C6 C7 102.39(17) . . ? O3 C7 C9 111.03(16) . . ? O3 C7 C6 103.34(16) . . ? C9 C7 C6 118.77(17) . . ? O4 C8 O3 121.4(2) . . ? O4 C8 C1 129.9(2) . . ? O3 C8 C1 108.75(17) . . ? O6 C9 C7 107.44(15) . . ? O6 C9 C10 102.95(16) . . ? C7 C9 C10 111.73(17) . . ? O5 C10 C9 105.42(16) . . ? O6 C11 O5 103.57(15) . . ? O6 C11 C12 109.41(16) . . ? O5 C11 C12 109.05(17) . . ? O6 C11 C16 112.20(16) . . ? O5 C11 C16 109.73(17) . . ? C12 C11 C16 112.48(18) . . ? C11 C12 C13 112.33(17) . . ? C14 C13 C12 111.86(19) . . ? C15 C14 C13 110.75(19) . . ? C14 C15 C16 110.64(17) . . ? C11 C16 C15 111.51(18) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.332 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.064 data_k53_99 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_contact_author_name 'Patrick Perlmutter' _publ_contact_author_address ; Department of Chemistry Monash University Clayton Victoria Australia 3800 ; _publ_requested_journal ? _publ_section_title ; The vitamin C route to the ciguatoxins. The enantioselective synthesis of a ring F building block. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 O7' _chemical_formula_weight 414.44 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 10.1336(2) _cell_length_b 9.5207(2) _cell_length_c 11.1957(2) _cell_angle_alpha 90 _cell_angle_beta 104.750(1) _cell_angle_gamma 90 _cell_volume 1044.55(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 CCD _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14784 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.88 _reflns_number_total 4923 _reflns_number_gt 4641 _reflns_threshold_expression >2sigma(I) _computing_data_collection ' Collect (Nonius, 1998) ' _computing_cell_refinement ' Denzo-SMN (Otwinowski and Major, 1997) ' _computing_data_reduction ' Denzo-SMN (Otwinowski and Major, 1997) ' _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^)+(0.0260P)^2^+0.2562P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(6) _refine_ls_number_reflns 4923 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'Fourier difference' 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 1.11798(10) 0.97974(10) 0.32051(9) 0.0263(2) Uani 1 1 d . . . O2 O 1.14136(9) 0.77387(10) 0.42313(9) 0.0231(2) Uani 1 1 d . . . O3 O 1.14462(9) 0.66593(11) 0.19855(9) 0.0257(2) Uani 1 1 d . . . O4 O 0.91871(8) 0.61507(9) 0.15696(8) 0.01806(18) Uani 1 1 d . . . O5 O 0.99760(11) 0.27903(12) 0.06103(10) 0.0327(2) Uani 1 1 d . . . O6 O 0.69414(9) 0.45067(10) 0.00881(8) 0.02015(19) Uani 1 1 d . . . O7 O 0.59504(10) 0.63404(13) -0.10839(14) 0.0491(4) Uani 1 1 d . . . C1 C 1.37443(16) 1.06783(17) 0.47987(13) 0.0308(3) Uani 1 1 d . . . H1 H 1.3377 1.1269 0.4111 0.037 Uiso 1 1 calc R . . C2 C 1.49399(18) 1.1056(2) 0.56637(15) 0.0413(4) Uani 1 1 d . . . H2 H 1.5385 1.1911 0.5570 0.050 Uiso 1 1 calc R . . C3 C 1.54824(16) 1.0189(2) 0.66599(15) 0.0397(4) Uani 1 1 d . . . H3 H 1.6305 1.0447 0.7241 0.048 Uiso 1 1 calc R . . C4 C 1.48333(16) 0.89537(18) 0.68130(14) 0.0333(3) Uani 1 1 d . . . H4 H 1.5208 0.8364 0.7500 0.040 Uiso 1 1 calc R . . C5 C 1.36333(14) 0.85728(15) 0.59630(12) 0.0231(3) Uani 1 1 d . . . H5 H 1.3180 0.7727 0.6072 0.028 Uiso 1 1 calc R . . C6 C 1.30931(13) 0.94351(14) 0.49476(11) 0.0187(2) Uani 1 1 d . . . C7 C 1.18071(13) 0.90493(14) 0.40222(11) 0.0191(3) Uani 1 1 d . . . C8 C 1.01458(13) 0.72414(14) 0.34577(13) 0.0221(3) Uani 1 1 d . . . H8 H 0.9441 0.8001 0.3303 0.026 Uiso 1 1 calc R . . C9 C 1.03751(13) 0.66979(13) 0.22496(12) 0.0181(2) Uani 1 1 d . . . C10 C 0.93093(12) 0.51570(14) 0.06273(11) 0.0183(2) Uani 1 1 d . . . H10 H 1.0085 0.5433 0.0275 0.022 Uiso 1 1 calc R . . C11 C 0.95560(13) 0.36806(14) 0.11822(12) 0.0212(3) Uani 1 1 d . . . C12 C 0.92447(15) 0.33833(15) 0.24135(13) 0.0258(3) Uani 1 1 d . . . H12A H 0.8468 0.3973 0.2496 0.031 Uiso 1 1 calc R . . H12B H 0.8978 0.2386 0.2445 0.031 Uiso 1 1 calc R . . C13 C 1.04715(16) 0.36865(15) 0.34720(13) 0.0281(3) Uani 1 1 d . . . H13 H 1.1190 0.3017 0.3613 0.034 Uiso 1 1 calc R . . C14 C 1.06585(16) 0.47886(16) 0.42302(13) 0.0288(3) Uani 1 1 d . . . H14 H 1.1469 0.4801 0.4882 0.035 Uiso 1 1 calc R . . C15 C 0.97096(15) 0.60071(16) 0.41498(13) 0.0278(3) Uani 1 1 d . . . H15A H 0.9700 0.6311 0.4993 0.033 Uiso 1 1 calc R . . H15B H 0.8773 0.5714 0.3716 0.033 Uiso 1 1 calc R . . C16 C 0.79943(13) 0.51079(14) -0.03953(11) 0.0195(2) Uani 1 1 d . . . H16 H 0.8135 0.4507 -0.1085 0.023 Uiso 1 1 calc R . . C17 C 0.73777(13) 0.65167(15) -0.09208(13) 0.0237(3) Uani 1 1 d . . . H17A H 0.7729 0.7292 -0.0337 0.028 Uiso 1 1 calc R . . H17B H 0.7591 0.6721 -0.1718 0.028 Uiso 1 1 calc R . . C18 C 0.56835(13) 0.49639(14) -0.07063(12) 0.0212(3) Uani 1 1 d . . . C19 C 0.52218(17) 0.40086(19) -0.18197(14) 0.0363(4) Uani 1 1 d . . . H19A H 0.5147 0.3033 -0.1538 0.044 Uiso 1 1 calc R . . H19B H 0.5910 0.4022 -0.2308 0.044 Uiso 1 1 calc R . . C20 C 0.38406(18) 0.4480(2) -0.26349(16) 0.0471(5) Uani 1 1 d . . . H20A H 0.3946 0.5404 -0.3006 0.056 Uiso 1 1 calc R . . H20B H 0.3528 0.3797 -0.3315 0.056 Uiso 1 1 calc R . . C21 C 0.27758(16) 0.45949(19) -0.19028(18) 0.0424(4) Uani 1 1 d . . . H21A H 0.1916 0.4965 -0.2442 0.051 Uiso 1 1 calc R . . H21B H 0.2588 0.3650 -0.1615 0.051 Uiso 1 1 calc R . . C22 C 0.32586(16) 0.5555(2) -0.08033(19) 0.0475(5) Uani 1 1 d . . . H22A H 0.2569 0.5576 -0.0316 0.057 Uiso 1 1 calc R . . H22B H 0.3361 0.6522 -0.1094 0.057 Uiso 1 1 calc R . . C23 C 0.46314(14) 0.5050(2) 0.00198(15) 0.0370(4) Uani 1 1 d . . . H23A H 0.4944 0.5709 0.0718 0.044 Uiso 1 1 calc R . . H23B H 0.4513 0.4114 0.0363 0.044 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 0.0282(5) 0.0252(5) 0.0217(5) 0.0040(4) -0.0008(4) 0.0011(4) O2 0.0226(4) 0.0186(4) 0.0235(5) 0.0001(4) -0.0022(4) -0.0037(4) O3 0.0152(4) 0.0338(5) 0.0268(5) 0.0019(4) 0.0033(4) -0.0023(4) O4 0.0145(4) 0.0182(4) 0.0203(4) -0.0027(3) 0.0022(3) 0.0003(3) O5 0.0301(5) 0.0299(5) 0.0343(5) -0.0087(5) 0.0013(5) 0.0136(5) O6 0.0155(4) 0.0219(4) 0.0206(4) 0.0026(4) 0.0002(3) -0.0017(3) O7 0.0171(5) 0.0290(6) 0.0948(10) 0.0307(7) 0.0022(6) -0.0007(4) C1 0.0352(8) 0.0326(8) 0.0229(7) 0.0040(6) 0.0044(6) -0.0104(6) C2 0.0397(9) 0.0476(10) 0.0359(8) -0.0027(8) 0.0083(7) -0.0257(8) C3 0.0269(7) 0.0559(11) 0.0317(8) -0.0092(8) -0.0011(6) -0.0120(7) C4 0.0338(8) 0.0366(8) 0.0229(7) -0.0007(6) -0.0052(6) 0.0033(7) C5 0.0265(7) 0.0220(7) 0.0193(6) -0.0005(5) 0.0033(5) 0.0002(5) C6 0.0195(6) 0.0209(6) 0.0162(5) -0.0022(5) 0.0053(5) 0.0003(5) C7 0.0209(6) 0.0198(6) 0.0169(6) -0.0014(5) 0.0054(5) 0.0002(5) C8 0.0183(6) 0.0217(6) 0.0240(6) -0.0023(5) 0.0014(5) -0.0020(5) C9 0.0163(6) 0.0153(5) 0.0203(6) 0.0038(5) 0.0002(5) -0.0001(5) C10 0.0166(6) 0.0202(6) 0.0183(6) -0.0024(5) 0.0051(5) 0.0017(5) C11 0.0151(6) 0.0210(6) 0.0235(6) -0.0036(5) -0.0022(5) 0.0023(5) C12 0.0302(7) 0.0193(6) 0.0258(7) 0.0008(5) 0.0034(6) -0.0044(5) C13 0.0325(7) 0.0228(7) 0.0252(7) 0.0078(5) 0.0004(6) -0.0020(6) C14 0.0358(8) 0.0289(7) 0.0185(6) 0.0064(5) 0.0013(5) -0.0080(6) C15 0.0323(7) 0.0303(8) 0.0228(6) -0.0061(6) 0.0110(6) -0.0116(6) C16 0.0180(6) 0.0219(6) 0.0181(6) -0.0006(5) 0.0037(5) 0.0002(5) C17 0.0184(6) 0.0251(7) 0.0253(6) 0.0061(5) 0.0014(5) -0.0015(5) C18 0.0182(6) 0.0170(6) 0.0256(6) 0.0046(5) 0.0005(5) 0.0013(5) C19 0.0348(8) 0.0396(9) 0.0253(7) -0.0058(7) -0.0090(6) 0.0091(7) C20 0.0417(10) 0.0485(10) 0.0354(9) 0.0006(8) -0.0188(7) 0.0053(8) C21 0.0236(7) 0.0313(8) 0.0591(11) 0.0075(8) -0.0136(7) -0.0060(6) C22 0.0183(7) 0.0558(11) 0.0662(12) -0.0144(10) 0.0066(8) 0.0002(7) C23 0.0211(7) 0.0534(10) 0.0357(8) -0.0104(8) 0.0054(6) -0.0029(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 C7 1.2051(16) . ? O2 C7 1.3485(16) . ? O2 C8 1.4346(15) . ? O3 C9 1.1959(16) . ? O4 C9 1.3541(15) . ? O4 C10 1.4456(15) . ? O5 C11 1.2035(17) . ? O6 C18 1.4241(15) . ? O6 C16 1.4328(16) . ? O7 C17 1.4209(16) . ? O7 C18 1.4239(17) . ? C1 C6 1.386(2) . ? C1 C2 1.392(2) . ? C2 C3 1.383(3) . ? C3 C4 1.380(2) . ? C4 C5 1.388(2) . ? C5 C6 1.3961(19) . ? C6 C7 1.4896(17) . ? C8 C9 1.5203(18) . ? C8 C15 1.5333(19) . ? C10 C16 1.5205(17) . ? C10 C11 1.5314(18) . ? C11 C12 1.5171(19) . ? C12 C13 1.5109(19) . ? C13 C14 1.333(2) . ? C14 C15 1.495(2) . ? C16 C17 1.5324(19) . ? C18 C23 1.498(2) . ? C18 C19 1.518(2) . ? C19 C20 1.531(2) . ? C20 C21 1.516(3) . ? C21 C22 1.511(3) . ? C22 C23 1.537(2) . ? 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 C7 O2 C8 117.36(10) . . ? C9 O4 C10 115.66(9) . . ? C18 O6 C16 106.03(9) . . ? C17 O7 C18 109.55(10) . . ? C6 C1 C2 119.57(14) . . ? C3 C2 C1 120.26(15) . . ? C4 C3 C2 120.28(14) . . ? C3 C4 C5 119.99(14) . . ? C4 C5 C6 119.87(13) . . ? C1 C6 C5 120.02(12) . . ? C1 C6 C7 119.08(12) . . ? C5 C6 C7 120.90(12) . . ? O1 C7 O2 123.81(12) . . ? O1 C7 C6 125.54(12) . . ? O2 C7 C6 110.64(11) . . ? O2 C8 C9 109.46(10) . . ? O2 C8 C15 106.08(11) . . ? C9 C8 C15 108.53(11) . . ? O3 C9 O4 125.60(12) . . ? O3 C9 C8 125.76(11) . . ? O4 C9 C8 108.41(10) . . ? O4 C10 C16 110.37(10) . . ? O4 C10 C11 109.88(10) . . ? C16 C10 C11 107.37(10) . . ? O5 C11 C12 122.38(13) . . ? O5 C11 C10 118.29(12) . . ? C12 C11 C10 119.32(11) . . ? C13 C12 C11 110.92(12) . . ? C14 C13 C12 127.24(14) . . ? C13 C14 C15 126.00(13) . . ? C14 C15 C8 111.19(11) . . ? O6 C16 C10 108.79(10) . . ? O6 C16 C17 102.98(10) . . ? C10 C16 C17 117.11(11) . . ? O7 C17 C16 104.37(10) . . ? O7 C18 O6 105.03(10) . . ? O7 C18 C23 109.02(13) . . ? O6 C18 C23 108.98(11) . . ? O7 C18 C19 110.48(13) . . ? O6 C18 C19 111.69(11) . . ? C23 C18 C19 111.42(13) . . ? C18 C19 C20 110.96(14) . . ? C21 C20 C19 111.56(14) . . ? C22 C21 C20 110.89(14) . . ? C21 C22 C23 110.78(15) . . ? C18 C23 C22 110.62(14) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.296 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.033