# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Mark Elliott' _publ_contact_author_email ELLIOTTMC@CARDIFF.AC.UK _publ_section_title ; Directed epoxidation of cyclohexa-1,4-dienes - stereoselective formation of up to six contiguous stereogenic centres ; loop_ _publ_author_name 'Mark Elliott' 'Dirk Bistra' 'Michael Butters' 'Joseph Hill-Cousins' 'Benson M Kariuki' # Attachment 'Compound 3b.cif' data_mce0801 _database_code_depnum_ccdc_archive 'CCDC 694523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H22 O4' _chemical_formula_sum 'C13 H22 O4' _chemical_formula_weight 242.31 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.8532(3) _cell_length_b 7.1565(2) _cell_length_c 16.0428(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.4210(10) _cell_angle_gamma 90.00 _cell_volume 1329.02(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2230 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.46 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20521 _diffrn_reflns_av_R_equivalents 0.1095 _diffrn_reflns_av_sigmaI/netI 0.1352 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3023 _reflns_number_gt 2230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0891P)^2^+0.3703P] 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 0.056(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3023 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2130 _refine_ls_wR_factor_gt 0.1923 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.3519(2) 0.3753(3) 0.78183(13) 0.0247(5) Uani 1 1 d . . . H1 H 0.2704 0.4052 0.7531 0.030 Uiso 1 1 calc R . . C2 C 0.4054(2) 0.2612(3) 0.72058(13) 0.0224(5) Uani 1 1 d . . . H2A H 0.3510 0.1652 0.6912 0.027 Uiso 1 1 calc R . . H2B H 0.4775 0.1995 0.7506 0.027 Uiso 1 1 calc R . . C3 C 0.43011(18) 0.4090(3) 0.65742(12) 0.0190(5) Uani 1 1 d . . . C4 C 0.32068(18) 0.4399(3) 0.59007(12) 0.0206(5) Uani 1 1 d . . . H4 H 0.2762 0.3244 0.5690 0.025 Uiso 1 1 calc R . . C5 C 0.25188(19) 0.6114(3) 0.58573(13) 0.0240(5) Uani 1 1 d . . . H5 H 0.1668 0.5985 0.5629 0.029 Uiso 1 1 calc R . . C6 C 0.2898(2) 0.7692(3) 0.64714(14) 0.0261(5) Uani 1 1 d . . . H6A H 0.2503 0.7583 0.6954 0.031 Uiso 1 1 calc R . . H6B H 0.2663 0.8893 0.6179 0.031 Uiso 1 1 calc R . . C7 C 0.4197(2) 0.7707(3) 0.68174(13) 0.0229(5) Uani 1 1 d . . . H7 H 0.4347 0.8594 0.7311 0.027 Uiso 1 1 calc R . . C8 C 0.46378(19) 0.5791(3) 0.71712(13) 0.0209(5) Uani 1 1 d . . . H8 H 0.5499 0.5844 0.7349 0.025 Uiso 1 1 calc R . . C9 C 0.52920(19) 0.3543(3) 0.61450(13) 0.0217(5) Uani 1 1 d . . . H9A H 0.5502 0.4639 0.5834 0.026 Uiso 1 1 calc R . . H9B H 0.5976 0.3201 0.6592 0.026 Uiso 1 1 calc R . . C10 C 0.3516(2) 0.2931(3) 0.86995(13) 0.0295(6) Uani 1 1 d . . . C11 C 0.2800(3) 0.1141(4) 0.85747(16) 0.0424(7) Uani 1 1 d . . . H11A H 0.3158 0.0233 0.8255 0.064 Uiso 1 1 calc R . . H11B H 0.2016 0.1424 0.8256 0.064 Uiso 1 1 calc R . . H11C H 0.2764 0.0617 0.9133 0.064 Uiso 1 1 calc R . . C12 C 0.4737(3) 0.2522(4) 0.91995(16) 0.0467(7) Uani 1 1 d . . . H12A H 0.4711 0.2159 0.9784 0.070 Uiso 1 1 calc R . . H12B H 0.5215 0.3642 0.9212 0.070 Uiso 1 1 calc R . . H12C H 0.5069 0.1500 0.8923 0.070 Uiso 1 1 calc R . . C13 C 0.2937(3) 0.4348(4) 0.91917(16) 0.0455(7) Uani 1 1 d . . . H13A H 0.2155 0.4619 0.8867 0.068 Uiso 1 1 calc R . . H13B H 0.3391 0.5504 0.9274 0.068 Uiso 1 1 calc R . . H13C H 0.2895 0.3826 0.9749 0.068 Uiso 1 1 calc R . . O1 O 0.41759(14) 0.5463(2) 0.79147(9) 0.0278(4) Uani 1 1 d . . . O2 O 0.32600(13) 0.57927(19) 0.52545(9) 0.0236(4) Uani 1 1 d . . . O3 O 0.48295(14) 0.8391(2) 0.62165(9) 0.0267(4) Uani 1 1 d . . . H3 H 0.4593 0.7862 0.5744 0.040 Uiso 1 1 calc R . . O4 O 0.50110(14) 0.2023(2) 0.55650(9) 0.0249(4) Uani 1 1 d . . . H4A H 0.4926 0.1048 0.5836 0.037 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 0.0286(12) 0.0213(11) 0.0265(11) -0.0007(8) 0.0114(9) -0.0022(9) C2 0.0295(12) 0.0148(10) 0.0263(10) 0.0010(8) 0.0138(9) -0.0018(8) C3 0.0235(11) 0.0131(9) 0.0227(10) -0.0014(7) 0.0097(9) 0.0006(8) C4 0.0229(11) 0.0187(10) 0.0233(10) 0.0011(7) 0.0118(9) -0.0040(8) C5 0.0216(12) 0.0247(11) 0.0276(10) 0.0016(8) 0.0095(9) 0.0002(9) C6 0.0290(13) 0.0191(10) 0.0330(11) 0.0003(8) 0.0126(10) 0.0051(9) C7 0.0290(12) 0.0137(10) 0.0295(10) -0.0022(8) 0.0138(9) -0.0017(8) C8 0.0230(11) 0.0165(10) 0.0248(10) -0.0023(8) 0.0085(9) -0.0017(8) C9 0.0235(12) 0.0181(10) 0.0262(10) -0.0021(8) 0.0111(9) -0.0019(8) C10 0.0356(14) 0.0321(12) 0.0242(11) 0.0002(9) 0.0143(10) -0.0078(10) C11 0.0560(19) 0.0404(15) 0.0370(13) 0.0029(11) 0.0235(13) -0.0124(13) C12 0.0496(18) 0.0600(19) 0.0305(12) 0.0128(12) 0.0084(12) -0.0028(14) C13 0.0614(19) 0.0471(16) 0.0360(13) -0.0100(11) 0.0284(14) -0.0083(14) O1 0.0417(10) 0.0190(8) 0.0268(8) -0.0042(6) 0.0166(7) -0.0066(7) O2 0.0258(9) 0.0224(8) 0.0253(7) 0.0033(6) 0.0112(7) 0.0006(6) O3 0.0345(10) 0.0184(8) 0.0304(8) -0.0008(6) 0.0141(7) -0.0058(6) O4 0.0362(9) 0.0147(7) 0.0279(8) -0.0021(6) 0.0159(7) -0.0009(6) _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 1.441(3) . ? C1 C2 1.517(3) . ? C1 C10 1.532(3) . ? C1 H1 1.0000 . ? C2 C3 1.536(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(3) . ? C3 C9 1.534(3) . ? C3 C8 1.548(3) . ? C4 O2 1.450(2) . ? C4 C5 1.467(3) . ? C4 H4 1.0000 . ? C5 O2 1.458(2) . ? C5 C6 1.502(3) . ? C5 H5 1.0000 . ? C6 C7 1.520(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O3 1.429(3) . ? C7 C8 1.532(3) . ? C7 H7 1.0000 . ? C8 O1 1.435(2) . ? C8 H8 1.0000 . ? C9 O4 1.424(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.525(4) . ? C10 C11 1.526(4) . ? C10 C13 1.535(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O3 H3 0.8400 . ? O4 H4A 0.8400 . ? 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 C2 103.60(16) . . ? O1 C1 C10 109.61(17) . . ? C2 C1 C10 118.39(19) . . ? O1 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? C10 C1 H1 108.3 . . ? C1 C2 C3 102.86(16) . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C4 C3 C9 109.75(16) . . ? C4 C3 C2 108.40(17) . . ? C9 C3 C2 113.18(16) . . ? C4 C3 C8 113.16(16) . . ? C9 C3 C8 110.97(17) . . ? C2 C3 C8 101.17(15) . . ? O2 C4 C5 59.99(13) . . ? O2 C4 C3 116.63(16) . . ? C5 C4 C3 122.56(17) . . ? O2 C4 H4 115.4 . . ? C5 C4 H4 115.4 . . ? C3 C4 H4 115.4 . . ? O2 C5 C4 59.42(13) . . ? O2 C5 C6 114.55(18) . . ? C4 C5 C6 120.85(18) . . ? O2 C5 H5 116.5 . . ? C4 C5 H5 116.5 . . ? C6 C5 H5 116.5 . . ? C5 C6 C7 112.41(18) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? O3 C7 C6 113.13(17) . . ? O3 C7 C8 111.73(18) . . ? C6 C7 C8 111.54(18) . . ? O3 C7 H7 106.7 . . ? C6 C7 H7 106.7 . . ? C8 C7 H7 106.7 . . ? O1 C8 C7 107.08(16) . . ? O1 C8 C3 106.98(15) . . ? C7 C8 C3 116.93(16) . . ? O1 C8 H8 108.5 . . ? C7 C8 H8 108.5 . . ? C3 C8 H8 108.5 . . ? O4 C9 C3 113.20(17) . . ? O4 C9 H9A 108.9 . . ? C3 C9 H9A 108.9 . . ? O4 C9 H9B 108.9 . . ? C3 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? C12 C10 C11 110.2(2) . . ? C12 C10 C1 111.64(19) . . ? C11 C10 C1 108.23(18) . . ? C12 C10 C13 109.6(2) . . ? C11 C10 C13 108.9(2) . . ? C1 C10 C13 108.1(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 O1 C1 110.11(14) . . ? C4 O2 C5 60.60(13) . . ? C7 O3 H3 109.5 . . ? C9 O4 H4A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.391 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.076 # Attachment 'Compound 13.cif' data_mce0801x _database_code_depnum_ccdc_archive 'CCDC 694524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 O4' _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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3080(2) _cell_length_b 13.5420(5) _cell_length_c 17.5900(7) _cell_angle_alpha 73.293(2) _cell_angle_beta 81.756(2) _cell_angle_gamma 79.108(2) _cell_volume 1406.88(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2977 _cell_measurement_theta_min 1.21 _cell_measurement_theta_max 24.73 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9578 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; Only poor quality crystals were available. The crystal used for data collection was twinned and hence the high residual values. ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7267 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.1311 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 24.73 _reflns_number_total 4761 _reflns_number_gt 2977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4761 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1888 _refine_ls_R_factor_gt 0.1401 _refine_ls_wR_factor_ref 0.3752 _refine_ls_wR_factor_gt 0.3427 _refine_ls_goodness_of_fit_ref 1.260 _refine_ls_restrained_S_all 1.260 _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 0.5130(10) 0.1409(4) 0.6217(3) 0.0346(15) Uani 1 1 d . . . H1 H 0.4245 0.1027 0.6005 0.042 Uiso 1 1 calc R . . C2 C 0.3641(9) 0.2071(4) 0.6694(3) 0.0254(13) Uani 1 1 d . . . H2A H 0.4430 0.2220 0.7086 0.030 Uiso 1 1 calc R . . H2B H 0.2406 0.1717 0.6981 0.030 Uiso 1 1 calc R . . C3 C 0.2850(9) 0.3083(4) 0.6065(3) 0.0226(13) Uani 1 1 d . . . C4 C 0.0814(9) 0.2967(4) 0.5771(3) 0.0260(13) Uani 1 1 d . . . H4 H -0.0256 0.2624 0.6194 0.031 Uiso 1 1 calc R . . C5 C 0.0758(9) 0.2823(4) 0.4974(3) 0.0262(13) Uani 1 1 d . . . H5 H -0.0319 0.2393 0.4927 0.031 Uiso 1 1 calc R . . C6 C 0.2766(9) 0.2837(4) 0.4391(3) 0.0219(12) Uani 1 1 d . . . H6 H 0.3547 0.2104 0.4481 0.026 Uiso 1 1 calc R . . C7 C 0.4300(9) 0.3498(4) 0.4552(3) 0.0226(13) Uani 1 1 d . . . H7 H 0.5702 0.3362 0.4226 0.027 Uiso 1 1 calc R . . C8 C 0.4811(9) 0.3155(4) 0.5423(3) 0.0215(12) Uani 1 1 d . . . H8 H 0.5691 0.3654 0.5502 0.026 Uiso 1 1 calc R . . C9 C 0.2177(11) 0.3199(5) 0.3536(3) 0.0402(16) Uani 1 1 d . . . H9A H 0.1293 0.2725 0.3450 0.060 Uiso 1 1 calc R . . H9B H 0.3504 0.3199 0.3170 0.060 Uiso 1 1 calc R . . H9C H 0.1353 0.3906 0.3435 0.060 Uiso 1 1 calc R . . C10 C 0.2305(9) 0.4028(4) 0.6421(3) 0.0294(14) Uani 1 1 d . . . H10A H 0.2025 0.4672 0.5983 0.035 Uiso 1 1 calc R . . H10B H 0.0956 0.3964 0.6784 0.035 Uiso 1 1 calc R . . C11 C 0.6890(11) 0.0640(4) 0.6655(3) 0.0340(15) Uani 1 1 d . . . H11A H 0.7614 0.1019 0.6922 0.041 Uiso 1 1 calc R . . H11B H 0.6187 0.0115 0.7080 0.041 Uiso 1 1 calc R . . C12 C 0.8616(12) 0.0065(5) 0.6196(4) 0.0450(18) Uani 1 1 d . . . H12A H 0.9267 0.0580 0.5746 0.054 Uiso 1 1 calc R . . H12B H 0.7930 -0.0372 0.5968 0.054 Uiso 1 1 calc R . . C13 C 1.0408(13) -0.0626(5) 0.6674(4) 0.053(2) Uani 1 1 d . . . H13A H 1.0993 -0.0204 0.6946 0.063 Uiso 1 1 calc R . . H13B H 0.9776 -0.1184 0.7091 0.063 Uiso 1 1 calc R . . C14 C 1.2251(13) -0.1125(5) 0.6201(4) 0.053(2) Uani 1 1 d . . . H14A H 1.1714 -0.1585 0.5958 0.079 Uiso 1 1 calc R . . H14B H 1.3358 -0.1534 0.6554 0.079 Uiso 1 1 calc R . . H14C H 1.2886 -0.0582 0.5781 0.079 Uiso 1 1 calc R . . C15 C 0.1977(11) 0.6374(5) 0.1169(3) 0.0364(16) Uani 1 1 d . . . H15 H 0.3407 0.6069 0.0939 0.044 Uiso 1 1 calc R . . C16 C 0.2411(10) 0.7040(4) 0.1657(3) 0.0308(14) Uani 1 1 d . . . H16A H 0.3680 0.6707 0.1962 0.037 Uiso 1 1 calc R . . H16B H 0.1136 0.7178 0.2033 0.037 Uiso 1 1 calc R . . C17 C 0.2868(9) 0.8054(4) 0.1028(3) 0.0237(13) Uani 1 1 d . . . C18 C 0.5230(9) 0.7933(4) 0.0720(3) 0.0267(14) Uani 1 1 d . . . H18 H 0.6253 0.7577 0.1136 0.032 Uiso 1 1 calc R . . C19 C 0.6006(10) 0.7816(5) -0.0079(4) 0.0355(15) Uani 1 1 d . . . H19 H 0.7465 0.7386 -0.0135 0.043 Uiso 1 1 calc R . . C20 C 0.4440(10) 0.7851(4) -0.0660(3) 0.0288(14) Uani 1 1 d . . . H20 H 0.4200 0.7120 -0.0591 0.035 Uiso 1 1 calc R . . C21 C 0.2245(9) 0.8490(4) -0.0470(3) 0.0243(13) Uani 1 1 d . . . H21 H 0.1204 0.8372 -0.0801 0.029 Uiso 1 1 calc R . . C22 C 0.1335(9) 0.8113(4) 0.0399(3) 0.0235(13) Uani 1 1 d . . . H22 H -0.0044 0.8584 0.0493 0.028 Uiso 1 1 calc R . . C23 C 0.2348(10) 0.9013(4) 0.1377(3) 0.0283(14) Uani 1 1 d . . . H23A H 0.3474 0.8969 0.1729 0.034 Uiso 1 1 calc R . . H23B H 0.2408 0.9657 0.0934 0.034 Uiso 1 1 calc R . . C24 C 0.5359(12) 0.8276(5) -0.1527(4) 0.0445(17) Uani 1 1 d . . . H24A H 0.5624 0.8991 -0.1610 0.067 Uiso 1 1 calc R . . H24B H 0.4314 0.8274 -0.1889 0.067 Uiso 1 1 calc R . . H24C H 0.6723 0.7834 -0.1637 0.067 Uiso 1 1 calc R . . C25 C 0.0719(11) 0.5488(5) 0.1577(4) 0.0359(15) Uani 1 1 d . . . H25A H -0.0737 0.5783 0.1780 0.043 Uiso 1 1 calc R . . H25B H 0.1466 0.5037 0.2043 0.043 Uiso 1 1 calc R . . C26 C 0.0450(15) 0.4817(5) 0.1050(4) 0.057(2) Uani 1 1 d . . . H26A H -0.0364 0.5261 0.0599 0.068 Uiso 1 1 calc R . . H26B H 0.1903 0.4550 0.0825 0.068 Uiso 1 1 calc R . . C27 C -0.0709(14) 0.3904(6) 0.1468(5) 0.058(2) Uani 1 1 d . . . H27A H -0.0600 0.3456 0.1104 0.070 Uiso 1 1 calc R . . H27B H 0.0059 0.3487 0.1938 0.070 Uiso 1 1 calc R . . C28 C -0.2944(19) 0.4158(9) 0.1730(7) 0.108(4) Uani 1 1 d . . . H28A H -0.3077 0.4562 0.2120 0.161 Uiso 1 1 calc R . . H28B H -0.3558 0.3514 0.1976 0.161 Uiso 1 1 calc R . . H28C H -0.3732 0.4573 0.1272 0.161 Uiso 1 1 calc R . . O1 O 0.6102(6) 0.2150(3) 0.5560(2) 0.0274(10) Uani 1 1 d . . . O2 O -0.0130(6) 0.3826(3) 0.5146(2) 0.0286(10) Uani 1 1 d . . . O3 O 0.3555(6) 0.4591(3) 0.4296(2) 0.0272(10) Uani 1 1 d . . . H3 H 0.2212 0.4709 0.4418 0.041 Uiso 1 1 calc R . . O4 O 0.3962(7) 0.4127(3) 0.6846(2) 0.0317(10) Uani 1 1 d . . . H4A H 0.4996 0.4345 0.6523 0.048 Uiso 1 1 calc R . . O5 O 0.0860(6) 0.7083(3) 0.0524(2) 0.0283(10) Uani 1 1 d . . . O6 O 0.5968(6) 0.8801(3) 0.0106(2) 0.0335(11) Uani 1 1 d . . . O7 O 0.2287(7) 0.9587(3) -0.0695(2) 0.0318(10) Uani 1 1 d . . . H7A H 0.3395 0.9702 -0.0541 0.048 Uiso 1 1 calc R . . O8 O 0.0298(7) 0.9087(3) 0.1813(2) 0.0344(11) Uani 1 1 d . . . H8A H -0.0654 0.9393 0.1500 0.052 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 0.031(4) 0.030(3) 0.034(3) 0.005(3) -0.003(3) -0.003(3) C2 0.019(3) 0.032(3) 0.020(3) -0.001(2) 0.000(2) -0.003(2) C3 0.011(3) 0.027(3) 0.025(3) -0.002(2) 0.005(2) -0.003(2) C4 0.014(3) 0.028(3) 0.029(3) 0.001(2) 0.002(2) -0.001(2) C5 0.014(3) 0.030(3) 0.034(3) -0.005(2) -0.005(2) -0.005(2) C6 0.015(3) 0.023(3) 0.027(3) -0.007(2) -0.004(2) 0.001(2) C7 0.021(3) 0.023(3) 0.022(3) -0.004(2) -0.003(2) 0.000(2) C8 0.012(3) 0.020(3) 0.031(3) -0.005(2) -0.001(2) -0.002(2) C9 0.040(4) 0.057(4) 0.026(3) -0.012(3) -0.012(3) -0.006(3) C10 0.018(3) 0.037(3) 0.030(3) -0.005(3) -0.003(2) -0.001(3) C11 0.043(4) 0.027(3) 0.025(3) -0.002(2) 0.000(3) 0.002(3) C12 0.060(5) 0.034(4) 0.034(4) -0.005(3) -0.003(3) 0.002(3) C13 0.067(6) 0.036(4) 0.047(4) -0.009(3) -0.008(4) 0.012(3) C14 0.056(5) 0.036(4) 0.067(5) -0.026(3) -0.013(4) 0.014(3) C15 0.048(4) 0.036(3) 0.025(3) -0.005(3) -0.011(3) -0.007(3) C16 0.037(4) 0.034(3) 0.018(3) -0.002(2) -0.010(3) -0.002(3) C17 0.014(3) 0.032(3) 0.028(3) -0.004(2) -0.013(2) -0.006(2) C18 0.018(3) 0.029(3) 0.040(3) 0.004(3) -0.015(2) -0.006(2) C19 0.020(4) 0.039(3) 0.044(4) -0.005(3) -0.008(3) 0.001(3) C20 0.030(4) 0.027(3) 0.026(3) -0.005(2) -0.003(3) -0.002(3) C21 0.021(3) 0.027(3) 0.025(3) -0.004(2) -0.010(2) -0.003(2) C22 0.013(3) 0.029(3) 0.030(3) -0.005(2) -0.007(2) -0.006(2) C23 0.025(4) 0.035(3) 0.025(3) -0.007(2) -0.005(2) -0.006(3) C24 0.040(5) 0.047(4) 0.043(4) -0.009(3) 0.000(3) -0.004(3) C25 0.039(4) 0.032(3) 0.037(3) -0.008(3) -0.008(3) -0.006(3) C26 0.086(7) 0.046(4) 0.041(4) -0.014(3) 0.001(4) -0.019(4) C27 0.074(6) 0.050(5) 0.056(5) -0.029(4) 0.008(4) -0.012(4) C28 0.096(9) 0.112(9) 0.141(10) -0.086(8) 0.050(8) -0.045(7) O1 0.017(2) 0.032(2) 0.027(2) -0.0006(16) -0.0011(16) -0.0001(17) O2 0.014(2) 0.037(2) 0.034(2) -0.0087(18) -0.0041(17) 0.0002(17) O3 0.014(2) 0.028(2) 0.035(2) -0.0036(17) 0.0004(17) -0.0014(16) O4 0.028(3) 0.041(2) 0.027(2) -0.0079(18) -0.0044(18) -0.009(2) O5 0.026(2) 0.032(2) 0.027(2) -0.0028(17) -0.0120(17) -0.0080(18) O6 0.021(2) 0.035(2) 0.044(2) -0.0064(19) -0.0057(19) -0.0087(19) O7 0.029(3) 0.029(2) 0.034(2) 0.0019(17) -0.0114(18) -0.0054(18) O8 0.030(3) 0.042(2) 0.029(2) -0.0068(19) -0.0052(18) 0.000(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 C1 O1 1.442(6) . ? C1 C11 1.502(9) . ? C1 C2 1.509(8) . ? C1 H1 1.0000 . ? C2 C3 1.542(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.503(8) . ? C3 C10 1.542(8) . ? C3 C8 1.548(7) . ? C4 O2 1.451(7) . ? C4 C5 1.475(8) . ? C4 H4 1.0000 . ? C5 O2 1.467(7) . ? C5 C6 1.511(8) . ? C5 H5 1.0000 . ? C6 C9 1.519(7) . ? C6 C7 1.539(7) . ? C6 H6 1.0000 . ? C7 O3 1.424(6) . ? C7 C8 1.530(7) . ? C7 H7 1.0000 . ? C8 O1 1.423(6) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O4 1.416(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.494(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.510(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.500(10) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O5 1.434(7) . ? C15 C16 1.493(8) . ? C15 C25 1.512(8) . ? C15 H15 1.0000 . ? C16 C17 1.541(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.506(8) . ? C17 C22 1.546(7) . ? C17 C23 1.553(8) . ? C18 O6 1.448(6) . ? C18 C19 1.463(8) . ? C18 H18 1.0000 . ? C19 O6 1.456(7) . ? C19 C20 1.506(8) . ? C19 H19 1.0000 . ? C20 C21 1.536(8) . ? C20 C24 1.537(8) . ? C20 H20 1.0000 . ? C21 O7 1.428(6) . ? C21 C22 1.529(7) . ? C21 H21 1.0000 . ? C22 O5 1.431(6) . ? C22 H22 1.0000 . ? C23 O8 1.408(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.517(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.507(9) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.428(13) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O3 H3 0.8400 . ? O4 H4A 0.8400 . ? O7 H7A 0.8400 . ? O8 H8A 0.8400 . ? 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 C11 109.2(5) . . ? O1 C1 C2 104.5(4) . . ? C11 C1 C2 115.7(5) . . ? O1 C1 H1 109.1 . . ? C11 C1 H1 109.1 . . ? C2 C1 H1 109.1 . . ? C1 C2 C3 104.4(4) . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C10 107.4(5) . . ? C4 C3 C2 109.3(4) . . ? C10 C3 C2 111.6(4) . . ? C4 C3 C8 113.5(4) . . ? C10 C3 C8 113.3(4) . . ? C2 C3 C8 101.8(4) . . ? O2 C4 C5 60.1(3) . . ? O2 C4 C3 117.5(4) . . ? C5 C4 C3 122.9(5) . . ? O2 C4 H4 115.0 . . ? C5 C4 H4 115.0 . . ? C3 C4 H4 115.0 . . ? O2 C5 C4 59.1(3) . . ? O2 C5 C6 114.9(4) . . ? C4 C5 C6 120.9(5) . . ? O2 C5 H5 116.5 . . ? C4 C5 H5 116.5 . . ? C6 C5 H5 116.5 . . ? C5 C6 C9 111.1(5) . . ? C5 C6 C7 110.5(4) . . ? C9 C6 C7 112.4(4) . . ? C5 C6 H6 107.5 . . ? C9 C6 H6 107.5 . . ? C7 C6 H6 107.5 . . ? O3 C7 C8 111.8(4) . . ? O3 C7 C6 113.0(4) . . ? C8 C7 C6 112.0(4) . . ? O3 C7 H7 106.5 . . ? C8 C7 H7 106.5 . . ? C6 C7 H7 106.5 . . ? O1 C8 C7 107.9(4) . . ? O1 C8 C3 107.4(4) . . ? C7 C8 C3 116.8(4) . . ? O1 C8 H8 108.2 . . ? C7 C8 H8 108.2 . . ? C3 C8 H8 108.2 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 C3 113.8(5) . . ? O4 C10 H10A 108.8 . . ? C3 C10 H10A 108.8 . . ? O4 C10 H10B 108.8 . . ? C3 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C1 118.9(5) . . ? C12 C11 H11A 107.6 . . ? C1 C11 H11A 107.6 . . ? C12 C11 H11B 107.6 . . ? C1 C11 H11B 107.6 . . ? H11A C11 H11B 107.0 . . ? C11 C12 C13 115.0(5) . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C12 115.2(6) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? 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 . . ? O5 C15 C16 105.2(5) . . ? O5 C15 C25 110.1(5) . . ? C16 C15 C25 118.0(5) . . ? O5 C15 H15 107.7 . . ? C16 C15 H15 107.7 . . ? C25 C15 H15 107.7 . . ? C15 C16 C17 103.4(4) . . ? C15 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? C15 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109.0 . . ? C18 C17 C16 109.2(5) . . ? C18 C17 C22 113.4(5) . . ? C16 C17 C22 101.0(4) . . ? C18 C17 C23 108.2(4) . . ? C16 C17 C23 112.2(4) . . ? C22 C17 C23 112.8(5) . . ? O6 C18 C19 60.0(3) . . ? O6 C18 C17 117.5(5) . . ? C19 C18 C17 123.3(5) . . ? O6 C18 H18 114.9 . . ? C19 C18 H18 114.9 . . ? C17 C18 H18 114.9 . . ? O6 C19 C18 59.5(4) . . ? O6 C19 C20 114.9(5) . . ? C18 C19 C20 121.0(5) . . ? O6 C19 H19 116.4 . . ? C18 C19 H19 116.4 . . ? C20 C19 H19 116.4 . . ? C19 C20 C21 110.2(5) . . ? C19 C20 C24 111.7(5) . . ? C21 C20 C24 111.5(5) . . ? C19 C20 H20 107.8 . . ? C21 C20 H20 107.8 . . ? C24 C20 H20 107.8 . . ? O7 C21 C22 111.3(4) . . ? O7 C21 C20 113.0(4) . . ? C22 C21 C20 112.6(4) . . ? O7 C21 H21 106.5 . . ? C22 C21 H21 106.5 . . ? C20 C21 H21 106.5 . . ? O5 C22 C21 107.8(4) . . ? O5 C22 C17 107.2(4) . . ? C21 C22 C17 115.5(4) . . ? O5 C22 H22 108.7 . . ? C21 C22 H22 108.7 . . ? C17 C22 H22 108.7 . . ? O8 C23 C17 113.0(4) . . ? O8 C23 H23A 109.0 . . ? C17 C23 H23A 109.0 . . ? O8 C23 H23B 109.0 . . ? C17 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C15 C25 C26 114.6(5) . . ? C15 C25 H25A 108.6 . . ? C26 C25 H25A 108.6 . . ? C15 C25 H25B 108.6 . . ? C26 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C27 C26 C25 114.5(6) . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26B 108.6 . . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C28 C27 C26 115.9(8) . . ? C28 C27 H27A 108.3 . . ? C26 C27 H27A 108.3 . . ? C28 C27 H27B 108.3 . . ? C26 C27 H27B 108.3 . . ? H27A C27 H27B 107.4 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C8 O1 C1 111.2(4) . . ? C4 O2 C5 60.7(4) . . ? C7 O3 H3 109.5 . . ? C10 O4 H4A 109.5 . . ? C22 O5 C15 110.0(4) . . ? C18 O6 C19 60.5(4) . . ? C21 O7 H7A 109.5 . . ? C23 O8 H8A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.73 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.867 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.151