Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Clive, Derrick L. J.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; 'Fletcher, Stephen P.' ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_name 'Dr. Derrick L. J. Clive' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton Alberta T6G 2G2 Canada ; _publ_contact_author_email derrick.clive@alberta.ca _publ_contact_author_fax '1(780)4928231' _publ_contact_author_phone '1(780)4923251' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data for a structure featured in a manuscript submitted to Chemical Communications (manuscript B205753K). Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis of the bicyclic dienone core of the antitumor agent ottelione B ; data_dlc0101 _database_code_CSD 190875 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C10 H14 O2' _chemical_formula_weight 166.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.8208(8) _cell_length_b 5.2546(7) _cell_length_c 14.1791(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.791(3) _cell_angle_gamma 90.00 _cell_volume 433.47(10) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1645 _cell_measurement_theta_min 2.874 _cell_measurement_theta_max 26.381 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9480 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/Smart 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2049 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.38 _reflns_number_total 1384 _reflns_number_gt 1246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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^)+(0.0546P)^2^+0.0051P] 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 -1.3(15) _refine_ls_number_reflns 1384 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3332(2) 0.3321(3) 0.46582(9) 0.0384(4) Uani 1 1 d . . . O2 O 0.3385(2) 0.7228(3) 0.40339(9) 0.0367(4) Uani 1 1 d . . . H2O H 0.4405 0.7465 0.4457 0.055 Uiso 1 1 calc R . . C1 C 0.2009(3) 0.3502(4) 0.24046(12) 0.0218(4) Uani 1 1 d . . . H1 H 0.2871 0.1884 0.2528 0.026 Uiso 1 1 calc R . . C2 C 0.0824(3) 0.4275(4) 0.33197(12) 0.0237(4) Uani 1 1 d . . . H2 H -0.0114 0.5840 0.3194 0.028 Uiso 1 1 calc R . . C3 C -0.0786(3) 0.2120(4) 0.36242(13) 0.0309(5) Uani 1 1 d . . . H3A H 0.0115 0.0890 0.4014 0.037 Uiso 1 1 calc R . . H3B H -0.1982 0.2851 0.4025 0.037 Uiso 1 1 calc R . . C4 C -0.1951(3) 0.0704(4) 0.28125(14) 0.0312(5) Uani 1 1 d . . . H4 H -0.3086 -0.0519 0.2960 0.037 Uiso 1 1 calc R . . C5 C -0.1505(3) 0.1044(4) 0.19172(14) 0.0299(4) Uani 1 1 d . . . H5 H -0.2276 0.0029 0.1452 0.036 Uiso 1 1 calc R . . C6 C 0.0196(3) 0.3003(4) 0.16201(12) 0.0265(4) Uani 1 1 d . . . H6 H -0.0659 0.4628 0.1500 0.032 Uiso 1 1 calc R . . C7 C 0.1711(3) 0.2517(4) 0.07747(13) 0.0331(5) Uani 1 1 d . . . H7A H 0.0830 0.2741 0.0172 0.040 Uiso 1 1 calc R . . H7B H 0.2371 0.0781 0.0797 0.040 Uiso 1 1 calc R . . C8 C 0.3610(3) 0.4560(4) 0.08935(13) 0.0331(5) Uani 1 1 d . . . H8A H 0.3269 0.6033 0.0477 0.040 Uiso 1 1 calc R . . H8B H 0.5120 0.3846 0.0730 0.040 Uiso 1 1 calc R . . C9 C 0.3638(3) 0.5390(4) 0.19437(12) 0.0271(4) Uani 1 1 d . . . H9A H 0.5207 0.5269 0.2231 0.033 Uiso 1 1 calc R . . H9B H 0.3077 0.7159 0.2008 0.033 Uiso 1 1 calc R . . C10 C 0.2629(3) 0.4865(4) 0.40799(12) 0.0250(4) 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 O1 0.0432(8) 0.0362(9) 0.0349(8) 0.0031(7) -0.0140(6) 0.0038(8) O2 0.0438(8) 0.0354(9) 0.0301(7) 0.0001(7) -0.0116(6) -0.0093(8) C1 0.0215(8) 0.0194(9) 0.0243(9) -0.0001(7) -0.0012(6) 0.0014(8) C2 0.0221(8) 0.0269(11) 0.0220(8) 0.0000(8) 0.0004(6) 0.0027(8) C3 0.0263(9) 0.0376(13) 0.0290(9) 0.0061(9) 0.0035(7) -0.0018(9) C4 0.0234(8) 0.0275(12) 0.0424(11) 0.0049(9) -0.0028(7) -0.0012(9) C5 0.0252(9) 0.0276(11) 0.0363(10) -0.0026(9) -0.0080(7) -0.0014(9) C6 0.0270(9) 0.0267(12) 0.0255(9) 0.0012(8) -0.0044(7) 0.0028(8) C7 0.0436(10) 0.0325(12) 0.0232(9) -0.0018(9) -0.0013(7) -0.0002(10) C8 0.0347(9) 0.0376(13) 0.0272(9) 0.0020(10) 0.0043(7) -0.0003(10) C9 0.0268(8) 0.0268(12) 0.0278(9) 0.0008(8) 0.0022(7) -0.0023(9) C10 0.0255(8) 0.0273(12) 0.0223(9) -0.0028(8) 0.0025(6) 0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.215(2) . ? O2 C10 1.320(2) . ? C1 C6 1.532(2) . ? C1 C9 1.533(2) . ? C1 C2 1.543(2) . ? C2 C10 1.514(2) . ? C2 C3 1.540(3) . ? C3 C4 1.513(3) . ? C4 C5 1.316(3) . ? C5 C6 1.498(3) . ? C6 C7 1.532(2) . ? C7 C8 1.546(3) . ? C8 C9 1.551(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 C6 C1 C9 102.86(14) . . ? C6 C1 C2 109.85(13) . . ? C9 C1 C2 119.16(16) . . ? C10 C2 C3 111.45(14) . . ? C10 C2 C1 109.50(13) . . ? C3 C2 C1 109.53(15) . . ? C4 C3 C2 114.23(15) . . ? C5 C4 C3 124.76(18) . . ? C4 C5 C6 121.09(18) . . ? C5 C6 C7 120.49(17) . . ? C5 C6 C1 111.10(14) . . ? C7 C6 C1 101.33(13) . . ? C6 C7 C8 103.07(16) . . ? C7 C8 C9 106.61(14) . . ? C1 C9 C8 103.83(16) . . ? O1 C10 O2 123.74(17) . . ? O1 C10 C2 123.75(19) . . ? O2 C10 C2 112.50(16) . . ? 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 C6 C1 C2 C10 -177.79(17) . . . . ? C9 C1 C2 C10 -59.6(2) . . . . ? C6 C1 C2 C3 59.71(18) . . . . ? C9 C1 C2 C3 177.90(15) . . . . ? C10 C2 C3 C4 -156.26(16) . . . . ? C1 C2 C3 C4 -34.9(2) . . . . ? C2 C3 C4 C5 6.7(3) . . . . ? C3 C4 C5 C6 -2.3(3) . . . . ? C4 C5 C6 C7 145.22(19) . . . . ? C4 C5 C6 C1 27.1(3) . . . . ? C9 C1 C6 C5 176.47(16) . . . . ? C2 C1 C6 C5 -55.7(2) . . . . ? C9 C1 C6 C7 47.28(17) . . . . ? C2 C1 C6 C7 175.15(17) . . . . ? C5 C6 C7 C8 -164.36(17) . . . . ? C1 C6 C7 C8 -41.41(19) . . . . ? C6 C7 C8 C9 20.6(2) . . . . ? C6 C1 C9 C8 -34.00(17) . . . . ? C2 C1 C9 C8 -155.76(15) . . . . ? C7 C8 C9 C1 8.2(2) . . . . ? C3 C2 C10 O1 27.2(2) . . . . ? C1 C2 C10 O1 -94.1(2) . . . . ? C3 C2 C10 O2 -153.95(15) . . . . ? C1 C2 C10 O2 84.70(19) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.231 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.037 data_compound(19) _database_code_CSD 189592 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C16 H32 O3 Si' _chemical_formula_weight 300.51 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4325(14) _cell_length_b 7.3565(10) _cell_length_c 11.6823(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.132(3) _cell_angle_gamma 90.00 _cell_volume 891.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2678 _cell_measurement_theta_min 2.489 _cell_measurement_theta_max 26.450 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9346 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5735 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.42 _reflns_number_total 3618 _reflns_number_gt 2689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldirck, 1997)' _computing_publication_material 'Bruker SHELXTL (Sheldirck, 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^)+(0.0591P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(17) _refine_ls_number_reflns 3618 _refine_ls_number_parameters 183 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si Si -0.03741(7) -0.00464(11) -0.28467(7) 0.0280(2) Uani 1 1 d . . . O1 O 0.10260(17) -0.1053(3) -0.25191(18) 0.0306(5) Uani 1 1 d . . . O2 O 0.39770(18) 0.0010(3) -0.07378(17) 0.0391(5) Uani 1 1 d . . . H2O H 0.4408 -0.0499 -0.0179 0.059 Uiso 1 1 calc R . . O3 O 0.4563(3) -0.6409(3) -0.1090(2) 0.0581(8) Uani 1 1 d D . . H3O H 0.4355 -0.7510 -0.1063 0.087 Uiso 1 1 calc R . . C1 C 0.3160(3) -0.0748(4) -0.3127(3) 0.0314(7) Uani 1 1 d . . . H1 H 0.4022 -0.0211 -0.2868 0.038 Uiso 1 1 calc R . . C2 C 0.2276(2) -0.0262(5) -0.2237(3) 0.0308(7) Uani 1 1 d . . . H2 H 0.2197 0.1089 -0.2185 0.037 Uiso 1 1 calc R . . C3 C 0.2834(3) -0.1029(4) -0.1070(3) 0.0324(7) Uani 1 1 d . . . H3 H 0.2203 -0.0816 -0.0497 0.039 Uiso 1 1 calc R . . C4 C 0.3107(3) -0.3048(4) -0.1128(3) 0.0312(7) Uani 1 1 d . . . H4A H 0.2275 -0.3704 -0.1252 0.037 Uiso 1 1 calc R . . H4B H 0.3544 -0.3442 -0.0375 0.037 Uiso 1 1 calc R . . C5 C 0.3939(3) -0.3610(4) -0.2073(3) 0.0299(7) Uani 1 1 d . . . H5 H 0.4824 -0.3096 -0.1886 0.036 Uiso 1 1 calc R . . C6 C 0.3345(3) -0.2797(4) -0.3212(2) 0.0295(7) Uani 1 1 d . . . H6 H 0.2474 -0.3357 -0.3398 0.035 Uiso 1 1 calc R . . C7 C 0.4068(3) -0.2977(5) -0.4276(3) 0.0434(9) Uani 1 1 d . . . H7A H 0.3973 -0.4215 -0.4606 0.052 Uiso 1 1 calc R . . H7B H 0.4996 -0.2705 -0.4089 0.052 Uiso 1 1 calc R . . C8 C 0.3408(4) -0.1544(5) -0.5114(3) 0.0515(10) Uani 1 1 d . . . H8A H 0.4050 -0.0957 -0.5560 0.062 Uiso 1 1 calc R . . H8B H 0.2739 -0.2123 -0.5660 0.062 Uiso 1 1 calc R . . C9 C 0.2807(3) -0.0156(6) -0.4377(3) 0.0471(8) Uani 1 1 d . . . H9A H 0.1859 -0.0132 -0.4566 0.056 Uiso 1 1 calc R . . H9B H 0.3152 0.1072 -0.4505 0.056 Uiso 1 1 calc R . . C10 C 0.4041(3) -0.5655(4) -0.2162(3) 0.0401(9) Uani 1 1 d . . . H10A H 0.3175 -0.6176 -0.2387 0.048 Uiso 1 1 calc R . . H10B H 0.4600 -0.5972 -0.2766 0.048 Uiso 1 1 calc R . . C11 C -0.0927(3) -0.0560(5) -0.4380(3) 0.0430(9) Uani 1 1 d . . . H11A H -0.0979 -0.1880 -0.4489 0.052 Uiso 1 1 calc R . . H11B H -0.0314 -0.0050 -0.4873 0.052 Uiso 1 1 calc R . . H11C H -0.1780 -0.0021 -0.4586 0.052 Uiso 1 1 calc R . . C12 C -0.0204(3) 0.2447(4) -0.2624(3) 0.0390(8) Uani 1 1 d . . . H12A H 0.0108 0.2692 -0.1817 0.047 Uiso 1 1 calc R . . H12B H -0.1044 0.3034 -0.2813 0.047 Uiso 1 1 calc R . . H12C H 0.0412 0.2931 -0.3123 0.047 Uiso 1 1 calc R . . C13 C -0.1538(3) -0.1042(4) -0.1892(3) 0.0356(8) Uani 1 1 d . . . C14 C -0.2846(3) -0.0062(7) -0.2086(3) 0.0519(9) Uani 1 1 d . . . H14A H -0.2725 0.1234 -0.1913 0.062 Uiso 1 1 calc R . . H14B H -0.3438 -0.0586 -0.1578 0.062 Uiso 1 1 calc R . . H14C H -0.3208 -0.0210 -0.2890 0.062 Uiso 1 1 calc R . . C15 C -0.1747(4) -0.3065(6) -0.2159(4) 0.0615(11) Uani 1 1 d . . . H15A H -0.2061 -0.3216 -0.2974 0.074 Uiso 1 1 calc R . . H15B H -0.2384 -0.3556 -0.1682 0.074 Uiso 1 1 calc R . . H15C H -0.0930 -0.3717 -0.1990 0.074 Uiso 1 1 calc R . . C16 C -0.1008(3) -0.0835(6) -0.0624(3) 0.0522(10) Uani 1 1 d . . . H16A H -0.0868 0.0455 -0.0444 0.063 Uiso 1 1 calc R . . H16B H -0.0188 -0.1491 -0.0482 0.063 Uiso 1 1 calc R . . H16C H -0.1628 -0.1339 -0.0135 0.063 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 Si 0.0222(4) 0.0303(4) 0.0301(4) -0.0044(4) -0.0032(3) 0.0035(4) O1 0.0183(10) 0.0285(12) 0.0435(13) -0.0025(10) -0.0030(9) 0.0020(9) O2 0.0360(11) 0.0297(11) 0.0470(12) 0.0034(13) -0.0171(9) -0.0065(12) O3 0.0751(18) 0.0289(13) 0.0604(17) 0.0032(12) -0.0386(15) 0.0002(13) C1 0.0186(15) 0.0380(18) 0.0360(18) 0.0098(14) -0.0039(13) -0.0028(13) C2 0.0207(14) 0.0300(19) 0.0402(16) 0.0020(16) -0.0043(12) -0.0006(14) C3 0.0278(16) 0.0364(18) 0.0322(17) -0.0021(15) 0.0000(13) -0.0025(14) C4 0.0280(16) 0.0327(17) 0.0316(17) 0.0065(14) -0.0036(13) -0.0047(14) C5 0.0225(15) 0.0319(18) 0.0334(17) 0.0004(14) -0.0058(13) -0.0031(13) C6 0.0192(15) 0.0378(19) 0.0311(17) 0.0024(14) 0.0003(12) -0.0018(13) C7 0.0273(18) 0.061(2) 0.041(2) -0.0047(18) 0.0018(15) -0.0045(17) C8 0.051(2) 0.063(3) 0.040(2) 0.0079(19) 0.0025(18) -0.021(2) C9 0.0340(16) 0.063(2) 0.0430(18) 0.019(2) -0.0006(14) -0.003(2) C10 0.0425(18) 0.0318(19) 0.043(2) -0.0003(15) -0.0089(16) 0.0018(14) C11 0.0328(17) 0.054(3) 0.0397(19) -0.0068(16) -0.0055(14) 0.0070(15) C12 0.0386(19) 0.0306(18) 0.046(2) 0.0021(15) -0.0035(16) 0.0056(15) C13 0.0253(16) 0.039(2) 0.0420(19) -0.0024(16) 0.0019(14) 0.0008(14) C14 0.0248(15) 0.066(2) 0.065(2) 0.000(3) 0.0047(15) 0.004(2) C15 0.060(3) 0.046(2) 0.080(3) 0.000(2) 0.018(2) -0.010(2) C16 0.043(2) 0.077(3) 0.038(2) 0.0040(19) 0.0109(16) 0.0054(19) _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 Si O1 1.646(2) . ? Si C12 1.859(3) . ? Si C11 1.861(3) . ? Si C13 1.883(3) . ? O1 C2 1.434(3) . ? O2 C3 1.435(4) . ? O3 C10 1.424(4) . ? C1 C2 1.505(4) . ? C1 C6 1.525(4) . ? C1 C9 1.530(4) . ? C2 C3 1.531(4) . ? C3 C4 1.515(4) . ? C4 C5 1.533(4) . ? C5 C10 1.512(5) . ? C5 C6 1.528(4) . ? C6 C7 1.527(4) . ? C7 C8 1.549(5) . ? C8 C9 1.514(5) . ? C13 C15 1.531(5) . ? C13 C16 1.533(5) . ? C13 C14 1.538(5) . ? 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 Si C12 110.02(13) . . ? O1 Si C11 107.98(13) . . ? C12 Si C11 110.52(16) . . ? O1 Si C13 107.45(13) . . ? C12 Si C13 111.02(15) . . ? C11 Si C13 109.75(16) . . ? C2 O1 Si 129.34(18) . . ? C2 C1 C6 111.7(2) . . ? C2 C1 C9 119.3(3) . . ? C6 C1 C9 103.8(3) . . ? O1 C2 C1 110.7(2) . . ? O1 C2 C3 107.8(3) . . ? C1 C2 C3 109.0(2) . . ? O2 C3 C4 112.3(2) . . ? O2 C3 C2 105.7(2) . . ? C4 C3 C2 112.1(3) . . ? C3 C4 C5 114.8(2) . . ? C10 C5 C6 110.7(3) . . ? C10 C5 C4 111.6(3) . . ? C6 C5 C4 108.3(2) . . ? C1 C6 C7 102.4(3) . . ? C1 C6 C5 111.9(2) . . ? C7 C6 C5 119.0(3) . . ? C6 C7 C8 103.4(3) . . ? C9 C8 C7 106.4(3) . . ? C8 C9 C1 106.2(3) . . ? O3 C10 C5 110.5(3) . . ? C15 C13 C16 108.8(3) . . ? C15 C13 C14 108.7(3) . . ? C16 C13 C14 108.6(3) . . ? C15 C13 Si 110.1(2) . . ? C16 C13 Si 110.2(2) . . ? C14 C13 Si 110.4(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 C12 Si O1 C2 -7.6(3) . . . . ? C11 Si O1 C2 113.1(3) . . . . ? C13 Si O1 C2 -128.5(3) . . . . ? Si O1 C2 C1 -115.9(3) . . . . ? Si O1 C2 C3 125.0(3) . . . . ? C6 C1 C2 O1 -60.5(3) . . . . ? C9 C1 C2 O1 60.8(4) . . . . ? C6 C1 C2 C3 57.9(3) . . . . ? C9 C1 C2 C3 179.2(3) . . . . ? O1 C2 C3 O2 -170.9(2) . . . . ? C1 C2 C3 O2 68.9(3) . . . . ? O1 C2 C3 C4 66.5(3) . . . . ? C1 C2 C3 C4 -53.7(3) . . . . ? O2 C3 C4 C5 -66.1(3) . . . . ? C2 C3 C4 C5 52.7(3) . . . . ? C3 C4 C5 C10 -173.5(3) . . . . ? C3 C4 C5 C6 -51.5(3) . . . . ? C2 C1 C6 C7 171.0(2) . . . . ? C9 C1 C6 C7 41.1(3) . . . . ? C2 C1 C6 C5 -60.4(3) . . . . ? C9 C1 C6 C5 169.7(2) . . . . ? C10 C5 C6 C1 176.8(3) . . . . ? C4 C5 C6 C1 54.2(3) . . . . ? C10 C5 C6 C7 -64.0(4) . . . . ? C4 C5 C6 C7 173.4(3) . . . . ? C1 C6 C7 C8 -39.5(3) . . . . ? C5 C6 C7 C8 -163.6(3) . . . . ? C6 C7 C8 C9 23.3(4) . . . . ? C7 C8 C9 C1 2.0(4) . . . . ? C2 C1 C9 C8 -151.8(3) . . . . ? C6 C1 C9 C8 -26.7(3) . . . . ? C6 C5 C10 O3 -178.5(3) . . . . ? C4 C5 C10 O3 -57.8(4) . . . . ? O1 Si C13 C15 -64.2(3) . . . . ? C12 Si C13 C15 175.4(2) . . . . ? C11 Si C13 C15 53.0(3) . . . . ? O1 Si C13 C16 55.8(3) . . . . ? C12 Si C13 C16 -64.6(3) . . . . ? C11 Si C13 C16 173.0(2) . . . . ? O1 Si C13 C14 175.7(2) . . . . ? C12 Si C13 C14 55.4(3) . . . . ? C11 Si C13 C14 -67.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.391 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.051 data_compound(14) _database_code_CSD 189593 _audit_creation_method 'manual editing of SHELXL template' _chemical_formula_sum 'C10 H15 I O3' _chemical_formula_weight 310.12 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6901(5) _cell_length_b 7.9975(5) _cell_length_c 18.4359(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1133.84(12) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5038 _cell_measurement_theta_min 2.266 _cell_measurement_theta_max 26.381 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.805 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5072 _exptl_absorpt_correction_T_max 0.8961 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5595 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2299 _reflns_number_gt 2147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 1997)' _computing_publication_material 'Bruker SHELXTL (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^)+(0.0320P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(3) _refine_ls_number_reflns 2299 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.30540(3) -0.43056(3) 0.109198(15) 0.03691(9) Uani 1 1 d . . . O1 O 0.5196(3) 0.0502(4) 0.05731(16) 0.0321(6) Uani 1 1 d . . . H1O H 0.4736 0.1184 0.0862 0.048 Uiso 1 1 calc R . . H1OB H 0.5251 0.0976 0.0167 0.048 Uiso 0.00 1 calc PR . . O2 O -0.0870(4) 0.2273(3) 0.04355(16) 0.0325(7) Uani 1 1 d . . . O3 O -0.1600(3) -0.0035(4) 0.10166(19) 0.0376(7) Uani 1 1 d . . . H3O H -0.2565 0.0153 0.0819 0.056 Uiso 1 1 calc R . . C1 C 0.3451(5) -0.0851(5) 0.1837(2) 0.0265(9) Uani 1 1 d . . . H1 H 0.4139 0.0208 0.1867 0.032 Uiso 1 1 calc R . . C2 C 0.4221(5) -0.1856(5) 0.1224(2) 0.0283(9) Uani 1 1 d . . . H2 H 0.5487 -0.2014 0.1326 0.034 Uiso 1 1 calc R . . C3 C 0.4045(5) -0.0898(6) 0.0503(2) 0.0276(9) Uani 1 1 d . . . H3 H 0.4449 -0.1626 0.0096 0.033 Uiso 1 1 calc R . . C4 C 0.2182(5) -0.0346(5) 0.0360(2) 0.0243(9) Uani 1 1 d . . . H4A H 0.1459 -0.1346 0.0265 0.029 Uiso 1 1 calc R . . H4B H 0.2159 0.0358 -0.0082 0.029 Uiso 1 1 calc R . . C5 C 0.1384(4) 0.0644(5) 0.0994(2) 0.0222(7) Uani 1 1 d . . . H5 H 0.2039 0.1718 0.1046 0.027 Uiso 1 1 calc R . . C6 C 0.1563(5) -0.0339(5) 0.1702(2) 0.0238(8) Uani 1 1 d . . . H6 H 0.0843 -0.1376 0.1662 0.029 Uiso 1 1 calc R . . C7 C 0.1078(6) 0.0557(7) 0.2407(2) 0.0402(10) Uani 1 1 d . . . H7A H -0.0190 0.0495 0.2496 0.048 Uiso 1 1 calc R . . H7B H 0.1432 0.1747 0.2390 0.048 Uiso 1 1 calc R . . C8 C 0.2093(7) -0.0394(6) 0.3000(2) 0.0439(11) Uani 1 1 d . . . H8A H 0.2734 0.0402 0.3313 0.053 Uiso 1 1 calc R . . H8B H 0.1285 -0.1047 0.3307 0.053 Uiso 1 1 calc R . . C9 C 0.3363(6) -0.1559(6) 0.2611(2) 0.0373(10) Uani 1 1 d . . . H9A H 0.2925 -0.2724 0.2609 0.045 Uiso 1 1 calc R . . H9B H 0.4521 -0.1536 0.2845 0.045 Uiso 1 1 calc R . . C10 C -0.0470(5) 0.1054(5) 0.0792(2) 0.0240(8) 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 I 0.04062(14) 0.02368(12) 0.04641(16) 0.00111(13) 0.00150(13) -0.00006(12) O1 0.0150(12) 0.0329(15) 0.0485(17) 0.0153(15) -0.0007(11) -0.0019(12) O2 0.0241(15) 0.0321(15) 0.0413(17) 0.0149(13) 0.0009(12) 0.0076(12) O3 0.0140(13) 0.0450(15) 0.0540(19) 0.0247(14) -0.0050(13) -0.0024(10) C1 0.0205(19) 0.0280(19) 0.031(2) 0.0028(19) -0.0085(14) -0.0018(16) C2 0.0169(17) 0.0266(19) 0.041(3) 0.0089(17) -0.0031(16) 0.0000(14) C3 0.0200(18) 0.030(2) 0.033(2) 0.0044(19) 0.0032(15) 0.0005(17) C4 0.0190(19) 0.029(2) 0.0253(19) 0.0031(15) 0.0000(14) -0.0008(15) C5 0.0137(14) 0.0251(16) 0.028(2) 0.006(2) 0.0004(12) -0.0015(14) C6 0.0190(19) 0.028(2) 0.0242(19) 0.0024(16) -0.0017(13) -0.0012(13) C7 0.044(2) 0.046(3) 0.031(2) -0.004(2) -0.0022(18) 0.006(2) C8 0.051(3) 0.054(3) 0.027(2) 0.0023(19) -0.005(2) -0.001(3) C9 0.039(3) 0.040(2) 0.033(2) 0.0039(19) -0.0121(18) -0.004(2) C10 0.0182(18) 0.027(2) 0.0262(18) 0.0011(15) 0.0016(14) 0.0021(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 I C2 2.169(4) . ? O1 C3 1.433(5) . ? O1 O3 2.631(3) 1_655 ? O2 C10 1.215(4) . ? O3 C10 1.298(4) . ? C1 C2 1.508(6) . ? C1 C6 1.530(5) . ? C1 C9 1.536(6) . ? C2 C3 1.540(5) . ? C3 C4 1.522(5) . ? C4 C5 1.540(5) . ? C5 C10 1.509(5) . ? C5 C6 1.530(5) . ? C6 C7 1.531(6) . ? C7 C8 1.544(6) . ? C8 C9 1.529(7) . ? 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 C3 O1 O3 118.6(2) . 1_655 ? C2 C1 C6 113.1(3) . . ? C2 C1 C9 121.1(4) . . ? C6 C1 C9 102.0(3) . . ? C1 C2 C3 110.3(3) . . ? C1 C2 I 113.8(3) . . ? C3 C2 I 108.4(3) . . ? O1 C3 C4 111.7(3) . . ? O1 C3 C2 104.9(3) . . ? C4 C3 C2 112.2(3) . . ? C3 C4 C5 113.1(3) . . ? C10 C5 C6 114.0(3) . . ? C10 C5 C4 107.5(3) . . ? C6 C5 C4 110.3(3) . . ? C1 C6 C5 111.2(3) . . ? C1 C6 C7 102.6(3) . . ? C5 C6 C7 117.5(4) . . ? C6 C7 C8 104.3(4) . . ? C9 C8 C7 106.9(4) . . ? C8 C9 C1 103.8(4) . . ? O2 C10 O3 122.8(3) . . ? O2 C10 C5 123.1(3) . . ? O3 C10 C5 114.1(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 C6 C1 C2 C3 55.1(4) . . . . ? C9 C1 C2 C3 176.6(3) . . . . ? C6 C1 C2 I -67.1(4) . . . . ? C9 C1 C2 I 54.4(4) . . . . ? O3 O1 C3 C4 170.9(2) 1_655 . . . ? O3 O1 C3 C2 49.2(4) 1_655 . . . ? C1 C2 C3 O1 68.6(4) . . . . ? I C2 C3 O1 -166.2(2) . . . . ? C1 C2 C3 C4 -52.9(5) . . . . ? I C2 C3 C4 72.4(4) . . . . ? O1 C3 C4 C5 -64.4(4) . . . . ? C2 C3 C4 C5 53.0(5) . . . . ? C3 C4 C5 C10 -177.9(3) . . . . ? C3 C4 C5 C6 -53.0(4) . . . . ? C2 C1 C6 C5 -56.6(5) . . . . ? C9 C1 C6 C5 171.7(3) . . . . ? C2 C1 C6 C7 177.0(3) . . . . ? C9 C1 C6 C7 45.2(4) . . . . ? C10 C5 C6 C1 174.7(3) . . . . ? C4 C5 C6 C1 53.6(5) . . . . ? C10 C5 C6 C7 -67.5(5) . . . . ? C4 C5 C6 C7 171.4(3) . . . . ? C1 C6 C7 C8 -34.2(4) . . . . ? C5 C6 C7 C8 -156.6(4) . . . . ? C6 C7 C8 C9 10.4(5) . . . . ? C7 C8 C9 C1 17.4(5) . . . . ? C2 C1 C9 C8 -165.2(4) . . . . ? C6 C1 C9 C8 -38.5(4) . . . . ? C6 C5 C10 O2 151.8(4) . . . . ? C4 C5 C10 O2 -85.6(5) . . . . ? C6 C5 C10 O3 -29.9(5) . . . . ? C4 C5 C10 O3 92.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.831 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.085