# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'J. Clark' 'A. Blake' 'Carine Guerot' 'Claire Wilson' _publ_contact_author_name 'J. Stephen Clark' _publ_contact_author_address ; Chemistry Department University of Glasgow Joseph Black Building University Avenue Glasgow G12 8QQ UNITED KINGDOM ; _publ_contact_author_email STEPHENC@CHEM.GLA.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Rapid synthesis of medium-ring fused polycarbocyclic systems by rearrangement of carbenoid-derived oxonium ylides ; data_hxhepo _database_code_depnum_ccdc_archive 'CCDC 650223' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O2' _chemical_formula_weight 248.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M '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 5.2434(5) _cell_length_b 9.3200(9) _cell_length_c 28.332(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1384.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2920 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.2 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.076 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ' sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7674 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.61 _reflns_number_total 1893 _reflns_number_gt 1694 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _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^] 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 ? _chemical_absolute_configuration syn #_refine_ls_abs_structure_details # 'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 2.0(15) # unreliable - light atom structure with Mo radiation _refine_ls_number_reflns 1893 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.4210(2) 0.06714(13) 0.05743(4) 0.0267(3) Uani 1 1 d . . . O2 O 0.7556(3) -0.15792(13) 0.05265(4) 0.0256(3) Uani 1 1 d . . . C1 C 0.4853(4) -0.1767(2) 0.14145(6) 0.0258(4) Uani 1 1 d . . . H1A H 0.3595 -0.0975 0.1406 0.031 Uiso 1 1 calc R . . H1B H 0.4471 -0.2426 0.1150 0.031 Uiso 1 1 calc R . . C2 C 0.4613(4) -0.2577(2) 0.18819(7) 0.0325(5) Uani 1 1 d . . . H2A H 0.2849 -0.2942 0.1917 0.039 Uiso 1 1 calc R . . H2B H 0.5784 -0.3410 0.1881 0.039 Uiso 1 1 calc R . . C3 C 0.5256(4) -0.1598(2) 0.22962(7) 0.0338(5) Uani 1 1 d . . . H3A H 0.5194 -0.2156 0.2593 0.041 Uiso 1 1 calc R . . H3B H 0.3970 -0.0823 0.2317 0.041 Uiso 1 1 calc R . . C4A C 0.8209(3) -0.01789(19) 0.17648(6) 0.0212(4) Uani 1 1 d . . . C4 C 0.7919(4) -0.0937(2) 0.22377(6) 0.0295(4) Uani 1 1 d . . . H4A H 0.8222 -0.0240 0.2496 0.035 Uiso 1 1 calc R . . H4B H 0.9220 -0.1702 0.2263 0.035 Uiso 1 1 calc R . . C5 C 0.8940(4) 0.11895(19) 0.17508(6) 0.0231(4) Uani 1 1 d . . . H5A H 0.9277 0.1613 0.2049 0.028 Uiso 1 1 calc R . . C5A C 0.9316(3) 0.21712(17) 0.13301(6) 0.0194(4) Uani 1 1 d . . . H5AA H 1.0797 0.1803 0.1143 0.023 Uiso 1 1 calc R . . C6 C 0.9967(4) 0.36959(18) 0.14997(6) 0.0260(4) Uani 1 1 d . . . H6A H 0.8556 0.4060 0.1699 0.031 Uiso 1 1 calc R . . H6B H 1.1526 0.3661 0.1697 0.031 Uiso 1 1 calc R . . C7 C 1.0395(4) 0.47237(18) 0.10899(7) 0.0282(4) Uani 1 1 d . . . H7A H 1.1908 0.4413 0.0907 0.034 Uiso 1 1 calc R . . H7B H 1.0736 0.5698 0.1214 0.034 Uiso 1 1 calc R . . C8 C 0.8074(4) 0.47703(19) 0.07651(8) 0.0322(5) Uani 1 1 d . . . H8A H 0.6600 0.5175 0.0938 0.039 Uiso 1 1 calc R . . H8B H 0.8437 0.5402 0.0492 0.039 Uiso 1 1 calc R . . C9A C 0.6979(3) 0.22263(18) 0.10016(6) 0.0189(4) Uani 1 1 d . . . H9AA H 0.5510 0.2599 0.1190 0.023 Uiso 1 1 calc R . . C9 C 0.7416(4) 0.32685(18) 0.05895(6) 0.0266(4) Uani 1 1 d . . . H9A H 0.8824 0.2906 0.0389 0.032 Uiso 1 1 calc R . . H9B H 0.5857 0.3314 0.0393 0.032 Uiso 1 1 calc R . . C10 C 0.6180(3) 0.07864(18) 0.07931(6) 0.0184(3) Uani 1 1 d . . . C11A C 0.7564(3) -0.11492(18) 0.13533(6) 0.0206(4) Uani 1 1 d . . . H11A H 0.8756 -0.1984 0.1374 0.025 Uiso 1 1 calc R . . C11 C 0.7973(3) -0.04871(17) 0.08613(5) 0.0189(4) Uani 1 1 d . . . H11B H 0.9776 -0.0147 0.0835 0.023 Uiso 1 1 calc R . . C12 C 0.8503(4) -0.1186(2) 0.00711(6) 0.0324(5) Uani 1 1 d . . . H12A H 0.8183 -0.1967 -0.0153 0.049 Uiso 1 1 calc R . . H12B H 1.0341 -0.1005 0.0091 0.049 Uiso 1 1 calc R . . H12C H 0.7634 -0.0315 -0.0037 0.049 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 0.0228(7) 0.0300(7) 0.0274(6) -0.0021(6) -0.0056(5) -0.0034(6) O2 0.0357(8) 0.0200(6) 0.0210(6) -0.0046(5) 0.0064(6) -0.0041(6) C1 0.0287(10) 0.0247(9) 0.0241(9) 0.0015(7) 0.0006(7) -0.0054(8) C2 0.0342(11) 0.0321(10) 0.0314(10) 0.0067(9) 0.0063(8) -0.0080(8) C3 0.0371(12) 0.0426(11) 0.0217(9) 0.0082(9) 0.0055(8) -0.0040(10) C4A 0.0191(8) 0.0276(9) 0.0168(8) 0.0030(7) -0.0007(7) 0.0011(7) C4 0.0328(11) 0.0352(10) 0.0204(8) 0.0071(8) -0.0019(8) -0.0023(9) C5 0.0222(9) 0.0299(9) 0.0172(8) -0.0029(7) -0.0025(7) -0.0001(7) C5A 0.0203(9) 0.0187(8) 0.0193(8) -0.0031(7) -0.0013(7) -0.0008(7) C6 0.0282(10) 0.0254(9) 0.0245(9) -0.0067(7) -0.0016(8) -0.0027(8) C7 0.0301(11) 0.0177(9) 0.0369(10) -0.0014(8) -0.0033(8) -0.0030(8) C8 0.0318(11) 0.0196(9) 0.0452(11) 0.0064(9) -0.0079(9) 0.0000(8) C9A 0.0189(8) 0.0173(8) 0.0206(8) -0.0020(6) -0.0009(7) 0.0025(7) C9 0.0306(10) 0.0224(9) 0.0267(9) 0.0037(7) -0.0067(8) -0.0008(8) C10 0.0183(8) 0.0214(8) 0.0156(7) 0.0011(7) 0.0024(6) -0.0019(7) C11A 0.0211(9) 0.0192(8) 0.0215(8) 0.0033(7) 0.0014(7) 0.0011(7) C11 0.0218(8) 0.0171(8) 0.0177(7) -0.0023(6) 0.0022(7) -0.0009(7) C12 0.0437(12) 0.0315(10) 0.0220(9) -0.0055(8) 0.0091(9) -0.0038(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.210(2) . ? O2 C11 1.4084(19) . ? O2 C12 1.430(2) . ? C1 C2 1.530(2) . ? C1 C11A 1.543(2) . ? C2 C3 1.525(3) . ? C3 C4 1.535(3) . ? C4A C5 1.332(3) . ? C4A C11A 1.514(2) . ? C4A C4 1.522(2) . ? C5 C5A 1.515(2) . ? C5A C6 1.538(2) . ? C5A C9A 1.540(2) . ? C6 C7 1.522(2) . ? C7 C8 1.526(3) . ? C8 C9 1.525(3) . ? C9A C10 1.525(2) . ? C9A C9 1.536(2) . ? C10 C11 1.526(2) . ? C11A C11 1.539(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 C11 O2 C12 111.62(13) . . ? C2 C1 C11A 110.95(15) . . ? C3 C2 C1 110.66(15) . . ? C2 C3 C4 111.00(17) . . ? C5 C4A C11A 127.82(15) . . ? C5 C4A C4 119.94(16) . . ? C11A C4A C4 112.24(14) . . ? C4A C4 C3 111.85(15) . . ? C4A C5 C5A 129.70(16) . . ? C5 C5A C6 109.92(13) . . ? C5 C5A C9A 113.07(14) . . ? C6 C5A C9A 109.55(14) . . ? C7 C6 C5A 112.07(14) . . ? C6 C7 C8 111.12(16) . . ? C9 C8 C7 110.55(15) . . ? C10 C9A C9 107.65(13) . . ? C10 C9A C5A 115.05(14) . . ? C9 C9A C5A 111.20(14) . . ? C8 C9 C9A 111.49(15) . . ? O1 C10 C9A 120.74(16) . . ? O1 C10 C11 121.47(15) . . ? C9A C10 C11 117.78(14) . . ? C4A C11A C11 115.26(13) . . ? C4A C11A C1 110.00(14) . . ? C11 C11A C1 112.32(14) . . ? O2 C11 C10 112.40(13) . . ? O2 C11 C11A 107.37(12) . . ? C10 C11 C11A 109.89(13) . . ? 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 C11A C1 C2 C3 57.7(2) . . . . ? C1 C2 C3 C4 -55.6(2) . . . . ? C5 C4A C4 C3 125.21(19) . . . . ? C11A C4A C4 C3 -54.3(2) . . . . ? C2 C3 C4 C4A 53.8(2) . . . . ? C11A C4A C5 C5A 0.6(3) . . . . ? C4 C4A C5 C5A -178.83(17) . . . . ? C4A C5 C5A C6 175.39(19) . . . . ? C4A C5 C5A C9A 52.6(3) . . . . ? C5 C5A C6 C7 179.34(16) . . . . ? C9A C5A C6 C7 -55.8(2) . . . . ? C5A C6 C7 C8 56.7(2) . . . . ? C6 C7 C8 C9 -56.0(2) . . . . ? C5 C5A C9A C10 -59.07(18) . . . . ? C6 C5A C9A C10 177.95(15) . . . . ? C5 C5A C9A C9 178.23(14) . . . . ? C6 C5A C9A C9 55.25(18) . . . . ? C7 C8 C9 C9A 56.1(2) . . . . ? C10 C9A C9 C8 176.66(15) . . . . ? C5A C9A C9 C8 -56.5(2) . . . . ? C9 C9A C10 O1 -63.9(2) . . . . ? C5A C9A C10 O1 171.57(15) . . . . ? C9 C9A C10 C11 114.87(15) . . . . ? C5A C9A C10 C11 -9.7(2) . . . . ? C5 C4A C11A C11 4.1(3) . . . . ? C4 C4A C11A C11 -176.34(15) . . . . ? C5 C4A C11A C1 -124.1(2) . . . . ? C4 C4A C11A C1 55.43(19) . . . . ? C2 C1 C11A C4A -57.17(19) . . . . ? C2 C1 C11A C11 173.00(14) . . . . ? C12 O2 C11 C10 73.78(18) . . . . ? C12 O2 C11 C11A -165.25(15) . . . . ? O1 C10 C11 O2 20.1(2) . . . . ? C9A C10 C11 O2 -158.66(14) . . . . ? O1 C10 C11 C11A -99.45(17) . . . . ? C9A C10 C11 C11A 81.83(18) . . . . ? C4A C11A C11 O2 173.60(14) . . . . ? C1 C11A C11 O2 -59.34(18) . . . . ? C4A C11A C11 C10 -63.86(18) . . . . ? C1 C11A C11 C10 63.20(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.333 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.044 data_mebzqu _database_code_depnum_ccdc_archive 'CCDC 650224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 O3' _chemical_formula_weight 300.38 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 5.4027(6) _cell_length_b 11.2344(13) _cell_length_c 13.4933(16) _cell_angle_alpha 97.311(2) _cell_angle_beta 95.227(2) _cell_angle_gamma 91.841(2) _cell_volume 808.16(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1711 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.082 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6346 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3546 _reflns_number_gt 2243 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _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^)+(0.0399P)^2^] 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 3546 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.37757(19) 0.28614(9) 0.65491(7) 0.0320(3) Uani 1 1 d . . . C1 C 0.8255(3) 0.20302(15) 0.49475(12) 0.0439(4) Uani 1 1 d . . . H1A H 0.9741 0.2310 0.5353 0.053 Uiso 1 1 calc R . . H1B H 0.8269 0.1855 0.4241 0.053 Uiso 1 1 calc R . . O2 O 0.27894(19) 0.25087(9) 0.91638(7) 0.0341(3) Uani 1 1 d . . . C2 C 0.6195(3) 0.18874(13) 0.53616(11) 0.0340(4) Uani 1 1 d . . . H2A H 0.4751 0.1606 0.4930 0.041 Uiso 1 1 calc R . . O3 O 0.0291(2) 0.40130(10) 1.35537(8) 0.0409(3) Uani 1 1 d . . . C3A C 0.5590(3) 0.10005(12) 0.69581(10) 0.0263(3) Uani 1 1 d . . . H3AA H 0.4016 0.0564 0.6641 0.032 Uiso 1 1 calc R . . C3 C 0.5921(3) 0.21292(13) 0.64564(10) 0.0293(3) Uani 1 1 d . . . H3A H 0.7427 0.2605 0.6797 0.035 Uiso 1 1 calc R . . C4 C 0.7697(3) 0.01423(13) 0.68377(11) 0.0325(4) Uani 1 1 d . . . H4A H 0.9285 0.0556 0.7139 0.039 Uiso 1 1 calc R . . H4B H 0.7845 -0.0100 0.6115 0.039 Uiso 1 1 calc R . . C5 C 0.7229(3) -0.09739(14) 0.73438(11) 0.0380(4) Uani 1 1 d . . . H5A H 0.5784 -0.1450 0.6973 0.046 Uiso 1 1 calc R . . H5B H 0.8697 -0.1477 0.7309 0.046 Uiso 1 1 calc R . . C6 C 0.6727(3) -0.06664(14) 0.84382(11) 0.0362(4) Uani 1 1 d . . . H6A H 0.8270 -0.0316 0.8835 0.043 Uiso 1 1 calc R . . H6B H 0.6245 -0.1411 0.8707 0.043 Uiso 1 1 calc R . . C7A C 0.5308(3) 0.13393(12) 0.80693(10) 0.0275(3) Uani 1 1 d . . . H7AA H 0.6972 0.1664 0.8394 0.033 Uiso 1 1 calc R . . C7 C 0.4663(3) 0.02224(13) 0.85540(11) 0.0340(4) Uani 1 1 d . . . H7A H 0.4475 0.0455 0.9275 0.041 Uiso 1 1 calc R . . H7B H 0.3066 -0.0158 0.8228 0.041 Uiso 1 1 calc R . . C8 C 0.3546(3) 0.23370(12) 0.82070(10) 0.0274(3) Uani 1 1 d . . . C9 C 0.2900(3) 0.30012(13) 0.74858(10) 0.0293(3) Uani 1 1 d . . . H9A H 0.1760 0.3613 0.7623 0.035 Uiso 1 1 calc R . . C10 C 0.1200(3) 0.34902(13) 0.93767(10) 0.0295(4) Uani 1 1 d . . . H10A H -0.0449 0.3315 0.8992 0.035 Uiso 1 1 calc R . . H10B H 0.1937 0.4234 0.9181 0.035 Uiso 1 1 calc R . . C11 C 0.0924(3) 0.36507(12) 1.04772(11) 0.0267(3) Uani 1 1 d . . . C12 C -0.1100(3) 0.31655(13) 1.08763(11) 0.0311(4) Uani 1 1 d . . . H12A H -0.2384 0.2726 1.0439 0.037 Uiso 1 1 calc R . . C13 C -0.1278(3) 0.33112(13) 1.18989(11) 0.0328(4) Uani 1 1 d . . . H13A H -0.2684 0.2980 1.2159 0.039 Uiso 1 1 calc R . . C14 C 0.0603(3) 0.39434(12) 1.25492(11) 0.0299(3) Uani 1 1 d . . . C15 C 0.2615(3) 0.44537(13) 1.21667(11) 0.0315(4) Uani 1 1 d . . . H15A H 0.3892 0.4900 1.2603 0.038 Uiso 1 1 calc R . . C16 C 0.2739(3) 0.43029(13) 1.11381(11) 0.0312(4) Uani 1 1 d . . . H16A H 0.4115 0.4659 1.0876 0.037 Uiso 1 1 calc R . . C17 C 0.2407(3) 0.44488(15) 1.42377(11) 0.0469(5) Uani 1 1 d . . . H17A H 0.1979 0.4460 1.4929 0.070 Uiso 1 1 calc R . . H17B H 0.2899 0.5264 1.4124 0.070 Uiso 1 1 calc R . . H17C H 0.3791 0.3920 1.4127 0.070 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 0.0358(6) 0.0309(6) 0.0306(6) 0.0069(4) 0.0035(5) 0.0093(5) C1 0.0463(11) 0.0477(11) 0.0398(10) 0.0100(8) 0.0084(8) 0.0039(9) O2 0.0434(7) 0.0284(6) 0.0318(6) 0.0029(4) 0.0077(5) 0.0142(5) C2 0.0370(10) 0.0307(9) 0.0345(9) 0.0072(7) 0.0005(7) 0.0018(7) O3 0.0472(7) 0.0429(7) 0.0328(6) 0.0047(5) 0.0055(5) 0.0003(6) C3A 0.0250(8) 0.0231(7) 0.0306(8) 0.0027(6) 0.0020(6) 0.0020(6) C3 0.0270(8) 0.0274(8) 0.0328(8) 0.0028(6) 0.0008(6) 0.0027(7) C4 0.0349(9) 0.0286(8) 0.0344(9) 0.0022(6) 0.0060(7) 0.0062(7) C5 0.0436(10) 0.0279(8) 0.0439(10) 0.0058(7) 0.0073(8) 0.0113(8) C6 0.0427(10) 0.0287(8) 0.0385(9) 0.0084(7) 0.0029(7) 0.0093(8) C7A 0.0291(8) 0.0235(8) 0.0294(8) 0.0031(6) 0.0001(6) 0.0049(7) C7 0.0405(10) 0.0308(9) 0.0327(9) 0.0076(7) 0.0059(7) 0.0090(7) C8 0.0306(9) 0.0221(7) 0.0285(8) -0.0003(6) 0.0022(6) 0.0021(7) C9 0.0292(9) 0.0243(8) 0.0332(8) -0.0007(6) 0.0021(7) 0.0040(7) C10 0.0281(9) 0.0223(8) 0.0381(9) 0.0015(6) 0.0040(7) 0.0070(7) C11 0.0258(8) 0.0193(7) 0.0352(8) 0.0028(6) 0.0030(6) 0.0064(6) C12 0.0278(9) 0.0247(8) 0.0396(9) 0.0019(6) -0.0006(7) 0.0022(7) C13 0.0282(9) 0.0287(8) 0.0430(10) 0.0083(7) 0.0073(7) 0.0013(7) C14 0.0351(9) 0.0229(8) 0.0330(9) 0.0047(6) 0.0055(7) 0.0083(7) C15 0.0318(9) 0.0255(8) 0.0362(9) 0.0016(6) 0.0008(7) 0.0004(7) C16 0.0269(9) 0.0281(8) 0.0392(9) 0.0046(7) 0.0065(7) 0.0009(7) C17 0.0600(12) 0.0432(10) 0.0353(10) 0.0033(8) -0.0028(8) -0.0010(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.3817(16) . ? O1 C3 1.4482(17) . ? C1 C2 1.304(2) . ? O2 C8 1.3817(16) . ? O2 C10 1.4357(16) . ? C2 C3 1.4893(19) . ? O3 C14 1.3738(17) . ? O3 C17 1.4337(18) . ? C3A C4 1.5218(19) . ? C3A C7A 1.5219(18) . ? C3A C3 1.5245(19) . ? C4 C5 1.527(2) . ? C5 C6 1.524(2) . ? C6 C7 1.526(2) . ? C7A C8 1.4983(19) . ? C7A C7 1.5317(19) . ? C8 C9 1.3286(19) . ? C10 C11 1.4945(19) . ? C11 C16 1.3863(19) . ? C11 C12 1.3879(19) . ? C12 C13 1.381(2) . ? C13 C14 1.393(2) . ? C14 C15 1.3837(19) . ? C15 C16 1.3846(19) . ? 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 C9 O1 C3 115.39(11) . . ? C8 O2 C10 116.27(10) . . ? C1 C2 C3 125.34(15) . . ? C14 O3 C17 116.40(13) . . ? C4 C3A C7A 109.38(11) . . ? C4 C3A C3 113.74(12) . . ? C7A C3A C3 110.13(11) . . ? O1 C3 C2 105.95(11) . . ? O1 C3 C3A 110.44(11) . . ? C2 C3 C3A 114.06(12) . . ? C3A C4 C5 110.97(12) . . ? C6 C5 C4 112.54(13) . . ? C5 C6 C7 111.66(12) . . ? C8 C7A C3A 109.93(11) . . ? C8 C7A C7 115.28(12) . . ? C3A C7A C7 110.56(12) . . ? C6 C7 C7A 109.57(12) . . ? C9 C8 O2 124.95(13) . . ? C9 C8 C7A 122.37(13) . . ? O2 C8 C7A 112.62(12) . . ? C8 C9 O1 124.39(14) . . ? O2 C10 C11 108.16(11) . . ? C16 C11 C12 117.75(13) . . ? C16 C11 C10 119.77(13) . . ? C12 C11 C10 122.48(13) . . ? C13 C12 C11 121.08(14) . . ? C12 C13 C14 120.05(14) . . ? O3 C14 C15 124.38(14) . . ? O3 C14 C13 115.77(14) . . ? C15 C14 C13 119.85(14) . . ? C14 C15 C16 118.94(14) . . ? C15 C16 C11 122.29(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C3 C2 168.19(11) . . . . ? C9 O1 C3 C3A 44.21(15) . . . . ? C1 C2 C3 O1 130.74(16) . . . . ? C1 C2 C3 C3A -107.58(18) . . . . ? C4 C3A C3 O1 176.40(11) . . . . ? C7A C3A C3 O1 -60.41(15) . . . . ? C4 C3A C3 C2 57.23(17) . . . . ? C7A C3A C3 C2 -179.59(12) . . . . ? C7A C3A C4 C5 57.23(15) . . . . ? C3 C3A C4 C5 -179.18(12) . . . . ? C3A C4 C5 C6 -53.51(17) . . . . ? C4 C5 C6 C7 52.46(18) . . . . ? C4 C3A C7A C8 170.50(11) . . . . ? C3 C3A C7A C8 44.80(16) . . . . ? C4 C3A C7A C7 -61.10(15) . . . . ? C3 C3A C7A C7 173.20(11) . . . . ? C5 C6 C7 C7A -54.80(16) . . . . ? C8 C7A C7 C6 -174.82(12) . . . . ? C3A C7A C7 C6 59.75(15) . . . . ? C10 O2 C8 C9 -0.4(2) . . . . ? C10 O2 C8 C7A 176.82(11) . . . . ? C3A C7A C8 C9 -15.91(19) . . . . ? C7 C7A C8 C9 -141.67(14) . . . . ? C3A C7A C8 O2 166.73(11) . . . . ? C7 C7A C8 O2 40.98(16) . . . . ? O2 C8 C9 O1 176.36(12) . . . . ? C7A C8 C9 O1 -0.7(2) . . . . ? C3 O1 C9 C8 -14.17(19) . . . . ? C8 O2 C10 C11 -171.04(11) . . . . ? O2 C10 C11 C16 82.70(16) . . . . ? O2 C10 C11 C12 -97.12(15) . . . . ? C16 C11 C12 C13 -1.0(2) . . . . ? C10 C11 C12 C13 178.79(14) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C17 O3 C14 C15 -12.0(2) . . . . ? C17 O3 C14 C13 168.18(13) . . . . ? C12 C13 C14 O3 -178.33(13) . . . . ? C12 C13 C14 C15 1.8(2) . . . . ? O3 C14 C15 C16 178.88(13) . . . . ? C13 C14 C15 C16 -1.3(2) . . . . ? C14 C15 C16 C11 -0.5(2) . . . . ? C12 C11 C16 C15 1.6(2) . . . . ? C10 C11 C16 C15 -178.23(13) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.205 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.037 data_trihxo _database_code_depnum_ccdc_archive 'CCDC 650225' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 O2' _chemical_formula_sum 'C16 H24 O2' _chemical_formula_weight 248.35 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 31.128(11) _cell_length_b 33.904(12) _cell_length_c 5.139(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5424(5) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2197 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 24.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.078 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8550 _diffrn_reflns_av_R_equivalents 0.101 _diffrn_reflns_av_sigmaI/netI 0.068 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.59 _reflns_number_total 1731 _reflns_number_gt 1354 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; ; _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^)+(0.047P)^2^] 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 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details . #_refine_ls_abs_structure_Flack #'not reliably determined: Friedel opposites merged' _refine_ls_number_reflns 1731 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 0.94 _refine_ls_restrained_S_all 0.94 _refine_ls_shift/su_max 0.001 _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 0.07813(7) 0.98796(6) 0.6910(5) 0.0250(5) Uani 1 1 d . . . O1 O 0.07595(5) 1.01134(4) 0.5102(3) 0.0354(4) Uani 1 1 d . . . C2 C 0.04539(6) 0.95715(6) 0.7247(5) 0.0249(5) Uani 1 1 d . . . H2 H 0.0241 0.9550 0.5798 0.030 Uiso 1 1 calc R . . C3 C 0.02850(6) 0.94550(6) 0.9924(5) 0.0252(5) Uani 1 1 d . . . H3 H 0.0420 0.9600 1.1408 0.030 Uiso 1 1 calc R . . C4 C -0.01883(6) 0.93577(7) 1.0301(5) 0.0306(6) Uani 1 1 d . . . H4A H -0.0359 0.9602 1.0072 0.037 Uiso 1 1 calc R . . H4B H -0.0233 0.9264 1.2105 0.037 Uiso 1 1 calc R . . C5 C -0.03539(7) 0.90446(7) 0.8415(5) 0.0337(6) Uani 1 1 d . . . H5A H -0.0641 0.8954 0.8981 0.040 Uiso 1 1 calc R . . H5B H -0.0382 0.9160 0.6655 0.040 Uiso 1 1 calc R . . C6 C -0.00470(7) 0.86955(7) 0.8322(6) 0.0383(6) Uani 1 1 d . . . H6A H -0.0175 0.8484 0.7246 0.046 Uiso 1 1 calc R . . H6B H -0.0006 0.8591 1.0104 0.046 Uiso 1 1 calc R . . C7 C 0.03882(6) 0.88117(6) 0.7191(6) 0.0281(5) Uani 1 1 d . . . H7A H 0.0355 0.8867 0.5310 0.034 Uiso 1 1 calc R . . H7B H 0.0590 0.8588 0.7381 0.034 Uiso 1 1 calc R . . C8 C 0.05794(6) 0.91773(6) 0.8537(5) 0.0224(5) Uani 1 1 d . . . C9 C 0.10377(6) 0.91465(6) 0.9720(5) 0.0231(5) Uani 1 1 d . . . H9 H 0.1012 0.9180 1.1647 0.028 Uiso 1 1 calc R . . O9 O 0.12288(4) 0.87725(4) 0.9240(3) 0.0304(4) Uani 1 1 d . . . C10 C 0.13560(6) 0.94535(6) 0.8717(5) 0.0243(5) Uani 1 1 d . . . H10A H 0.1429 0.9387 0.6875 0.029 Uiso 1 1 calc R . . C11 C 0.17695(6) 0.94384(6) 1.0330(5) 0.0315(6) Uani 1 1 d . . . H11A H 0.1698 0.9478 1.2188 0.038 Uiso 1 1 calc R . . H11B H 0.1901 0.9174 1.0152 0.038 Uiso 1 1 calc R . . C12 C 0.20958(6) 0.97505(7) 0.9492(7) 0.0377(6) Uani 1 1 d . . . H12A H 0.2354 0.9734 1.0610 0.045 Uiso 1 1 calc R . . H12B H 0.2185 0.9702 0.7671 0.045 Uiso 1 1 calc R . . C13 C 0.18979(7) 1.01596(6) 0.9717(6) 0.0355(6) Uani 1 1 d . . . H13A H 0.2109 1.0359 0.9132 0.043 Uiso 1 1 calc R . . H13B H 0.1827 1.0214 1.1560 0.043 Uiso 1 1 calc R . . C14 C 0.14922(7) 1.01915(6) 0.8075(5) 0.0312(6) Uani 1 1 d . . . H14A H 0.1569 1.0166 0.6214 0.037 Uiso 1 1 calc R . . H14B H 0.1363 1.0455 0.8334 0.037 Uiso 1 1 calc R . . C15 C 0.11601(6) 0.98742(6) 0.8768(5) 0.0246(5) Uani 1 1 d . . . H15 H 0.1051 0.9928 1.0564 0.030 Uiso 1 1 calc R . . C16 C 0.11562(8) 0.84957(7) 1.1283(6) 0.0391(7) Uani 1 1 d . . . H16C H 0.1295 0.8245 1.0847 0.059 Uiso 1 1 calc R . . H16D H 0.0847 0.8454 1.1497 0.059 Uiso 1 1 calc R . . H16A H 0.1277 0.8598 1.2909 0.059 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 0.0309(11) 0.0189(10) 0.0254(13) 0.0012(10) 0.0038(10) 0.0051(9) O1 0.0445(9) 0.0303(9) 0.0314(10) 0.0091(8) -0.0032(8) -0.0019(7) C2 0.0255(10) 0.0246(11) 0.0245(12) 0.0033(10) -0.0043(10) 0.0038(9) C3 0.0254(10) 0.0269(11) 0.0234(12) 0.0014(11) 0.0003(10) 0.0026(9) C4 0.0240(11) 0.0386(14) 0.0292(14) 0.0042(11) 0.0049(10) 0.0059(10) C5 0.0222(11) 0.0455(15) 0.0334(14) 0.0070(12) 0.0010(11) -0.0045(10) C6 0.0326(13) 0.0348(13) 0.0476(17) 0.0023(13) -0.0013(13) -0.0095(11) C7 0.0274(11) 0.0237(11) 0.0333(13) -0.0006(11) 0.0000(11) -0.0011(9) C8 0.0209(10) 0.0227(11) 0.0236(11) 0.0016(10) 0.0016(9) 0.0015(9) C9 0.0214(10) 0.0198(11) 0.0281(12) 0.0016(10) 0.0037(10) 0.0030(8) O9 0.0253(7) 0.0189(8) 0.0470(12) 0.0046(8) 0.0050(7) 0.0039(6) C10 0.0219(10) 0.0230(12) 0.0279(12) -0.0001(10) 0.0046(9) -0.0007(9) C11 0.0257(11) 0.0260(12) 0.0427(16) 0.0003(11) -0.0018(11) -0.0008(9) C12 0.0259(11) 0.0326(13) 0.0547(18) -0.0052(13) 0.0007(12) -0.0043(10) C13 0.0313(12) 0.0276(12) 0.0475(16) -0.0056(13) 0.0046(12) -0.0074(10) C14 0.0365(12) 0.0219(11) 0.0351(15) 0.0018(11) 0.0046(11) -0.0046(10) C15 0.0258(11) 0.0211(11) 0.0270(12) 0.0003(10) 0.0044(10) 0.0009(9) C16 0.0371(13) 0.0258(12) 0.0543(18) 0.0156(13) -0.0073(13) -0.0001(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 C1 O1 1.223(3) . ? C1 C2 1.470(3) . ? C1 C15 1.517(3) . ? C2 C3 1.525(3) . ? C2 C8 1.542(3) . ? C2 H2 1.0000 . ? C3 C8 1.495(3) . ? C3 C4 1.522(3) . ? C3 H3 1.0000 . ? C4 C5 1.527(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.522(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.539(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.554(3) . ? C9 O9 1.422(2) . ? C9 C10 1.526(3) . ? C9 H9 1.0000 . ? O9 C16 1.426(3) . ? C10 C11 1.532(3) . ? C10 C15 1.551(3) . ? C10 H10A 1.0000 . ? C11 C12 1.529(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.523(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.534(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15 1.0000 . ? C16 H16C 0.9800 . ? C16 H16D 0.9800 . ? C16 H16A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.8(2) . . ? O1 C1 C15 121.9(2) . . ? C2 C1 C15 117.14(19) . . ? C1 C2 C3 122.0(2) . . ? C1 C2 C8 119.40(17) . . ? C3 C2 C8 58.33(15) . . ? C1 C2 H2 115.1 . . ? C3 C2 H2 115.1 . . ? C8 C2 H2 115.1 . . ? C8 C3 C4 121.18(19) . . ? C8 C3 C2 61.43(15) . . ? C4 C3 C2 120.31(19) . . ? C8 C3 H3 114.6 . . ? C4 C3 H3 114.6 . . ? C2 C3 H3 114.6 . . ? C3 C4 C5 113.37(19) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 110.4(2) . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5B 109.6 . . ? C4 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 C7 111.62(19) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 112.3(2) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C3 C8 C7 118.97(17) . . ? C3 C8 C2 60.24(14) . . ? C7 C8 C2 114.02(19) . . ? C3 C8 C9 114.74(19) . . ? C7 C8 C9 118.46(17) . . ? C2 C8 C9 117.32(17) . . ? O9 C9 C10 106.14(16) . . ? O9 C9 C8 112.08(18) . . ? C10 C9 C8 114.69(17) . . ? O9 C9 H9 107.9 . . ? C10 C9 H9 107.9 . . ? C8 C9 H9 107.9 . . ? C9 O9 C16 113.13(18) . . ? C9 C10 C11 109.87(18) . . ? C9 C10 C15 111.49(16) . . ? C11 C10 C15 110.60(18) . . ? C9 C10 H10A 108.3 . . ? C11 C10 H10A 108.3 . . ? C15 C10 H10A 108.3 . . ? C12 C11 C10 112.5(2) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 109.92(18) . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C12 C13 C14 111.0(2) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C15 112.37(19) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C1 C15 C14 111.67(19) . . ? C1 C15 C10 107.82(18) . . ? C14 C15 C10 112.10(16) . . ? C1 C15 H15 108.4 . . ? C14 C15 H15 108.4 . . ? C10 C15 H15 108.4 . . ? O9 C16 H16C 109.5 . . ? O9 C16 H16D 109.5 . . ? H16C C16 H16D 109.5 . . ? O9 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16D C16 H16A 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 O1 C1 C2 C3 -140.6(2) . . . . ? C15 C1 C2 C3 43.8(3) . . . . ? O1 C1 C2 C8 150.4(2) . . . . ? C15 C1 C2 C8 -25.2(3) . . . . ? C1 C2 C3 C8 -107.1(2) . . . . ? C1 C2 C3 C4 141.5(2) . . . . ? C8 C2 C3 C4 -111.4(2) . . . . ? C8 C3 C4 C5 -19.8(3) . . . . ? C2 C3 C4 C5 53.1(3) . . . . ? C3 C4 C5 C6 47.5(3) . . . . ? C4 C5 C6 C7 -65.2(3) . . . . ? C5 C6 C7 C8 51.3(3) . . . . ? C4 C3 C8 C7 7.3(3) . . . . ? C2 C3 C8 C7 -102.7(2) . . . . ? C4 C3 C8 C2 110.0(2) . . . . ? C4 C3 C8 C9 -141.4(2) . . . . ? C2 C3 C8 C9 108.6(2) . . . . ? C6 C7 C8 C3 -22.5(3) . . . . ? C6 C7 C8 C2 -90.5(2) . . . . ? C6 C7 C8 C9 125.1(2) . . . . ? C1 C2 C8 C3 111.5(2) . . . . ? C1 C2 C8 C7 -137.6(2) . . . . ? C3 C2 C8 C7 110.9(2) . . . . ? C1 C2 C8 C9 7.2(3) . . . . ? C3 C2 C8 C9 -104.3(2) . . . . ? C3 C8 C9 O9 152.04(18) . . . . ? C7 C8 C9 O9 3.1(3) . . . . ? C2 C8 C9 O9 -140.1(2) . . . . ? C3 C8 C9 C10 -86.9(2) . . . . ? C7 C8 C9 C10 124.2(2) . . . . ? C2 C8 C9 C10 -19.0(3) . . . . ? C10 C9 O9 C16 141.45(18) . . . . ? C8 C9 O9 C16 -92.6(2) . . . . ? O9 C9 C10 C11 -65.0(2) . . . . ? C8 C9 C10 C11 170.7(2) . . . . ? O9 C9 C10 C15 172.02(19) . . . . ? C8 C9 C10 C15 47.7(3) . . . . ? C9 C10 C11 C12 -177.7(2) . . . . ? C15 C10 C11 C12 -54.2(3) . . . . ? C10 C11 C12 C13 58.0(3) . . . . ? C11 C12 C13 C14 -57.8(3) . . . . ? C12 C13 C14 C15 55.8(3) . . . . ? O1 C1 C15 C14 0.3(3) . . . . ? C2 C1 C15 C14 175.83(19) . . . . ? O1 C1 C15 C10 -123.3(2) . . . . ? C2 C1 C15 C10 52.3(2) . . . . ? C13 C14 C15 C1 -173.3(2) . . . . ? C13 C14 C15 C10 -52.2(3) . . . . ? C9 C10 C15 C1 -63.5(2) . . . . ? C11 C10 C15 C1 173.97(18) . . . . ? C9 C10 C15 C14 173.2(2) . . . . ? C11 C10 C15 C14 50.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.18 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 #===END of CIF trihxo #===end of CIF