# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Brian P. Roberts' 'Hai-Shan Dang' 'D. Tocher' _publ_contact_author_name 'Dr Brian P Roberts' _publ_contact_author_address ; Department of Chemistry University College London Christopher Ingold Laboratories 20 Gordon Street London WC1H OAJ UNITED KINGDOM ; _publ_contact_author_email B.P.ROBERTS@UCL.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid dios ; data_str0166_Compound_58 _database_code_CSD 216435 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 O2' _chemical_formula_weight 288.41 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5195(11) _cell_length_b 10.0386(13) _cell_length_c 19.370(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1656.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14785 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3974 _reflns_number_gt 3275 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.0651P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.0(13) _refine_ls_number_reflns 3974 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O1 O 0.09853(12) 0.15854(11) 1.01911(5) 0.0363(3) Uani 1 1 d . . . O2 O 0.12026(14) 0.36812(11) 0.97244(5) 0.0423(3) Uani 1 1 d . . . C1 C 0.1739(2) 0.28297(16) 1.02415(8) 0.0364(4) Uani 1 1 d . . . H1 H 0.2874 0.2704 1.0189 0.044 Uiso 1 1 calc R . . C2 C 0.14091(19) 0.34320(17) 1.09380(8) 0.0375(4) Uani 1 1 d . . . C3 C 0.1198(2) 0.47872(18) 1.10138(9) 0.0470(5) Uani 1 1 d . . . H3 H 0.1198 0.5334 1.0626 0.056 Uiso 1 1 calc R . . C4 C 0.0985(2) 0.5341(2) 1.16628(10) 0.0581(5) Uani 1 1 d . . . H4 H 0.0841 0.6256 1.1706 0.070 Uiso 1 1 calc R . . C5 C 0.0986(3) 0.4559(2) 1.22370(10) 0.0591(6) Uani 1 1 d . . . H5 H 0.0845 0.4936 1.2671 0.071 Uiso 1 1 calc R . . C6 C 0.1196(3) 0.3209(2) 1.21706(10) 0.0582(5) Uani 1 1 d . . . H6 H 0.1195 0.2670 1.2561 0.070 Uiso 1 1 calc R . . C7 C 0.1408(2) 0.2644(2) 1.15244(9) 0.0487(4) Uani 1 1 d . . . H7 H 0.1551 0.1728 1.1485 0.058 Uiso 1 1 calc R . . C8 C 0.0925(3) 0.4280(2) 0.85756(9) 0.0586(6) Uani 1 1 d . . . H8A H -0.0193 0.4164 0.8557 0.088 Uiso 1 1 calc R . . H8B H 0.1355 0.4189 0.8120 0.088 Uiso 1 1 calc R . . H8C H 0.1163 0.5150 0.8753 0.088 Uiso 1 1 calc R . . C9 C 0.1634(2) 0.32299(18) 0.90452(8) 0.0409(4) Uani 1 1 d . . . H9 H 0.2780 0.3251 0.9000 0.049 Uiso 1 1 calc R . . C10 C 0.1053(2) 0.17975(17) 0.89320(8) 0.0380(4) Uani 1 1 d . . . H10 H -0.0093 0.1822 0.8889 0.046 Uiso 1 1 calc R . . C11 C 0.14647(19) 0.09394(16) 0.95619(8) 0.0347(4) Uani 1 1 d . . . H11 H 0.2607 0.0829 0.9575 0.042 Uiso 1 1 calc R . . C12 C 0.0720(2) -0.04398(17) 0.95364(9) 0.0408(4) Uani 1 1 d . . . H12 H -0.0413 -0.0317 0.9478 0.049 Uiso 1 1 calc R . . C13 C 0.0970(2) -0.13141(17) 1.01822(9) 0.0484(5) Uani 1 1 d . . . H13 H 0.0811 -0.2237 1.0034 0.058 Uiso 1 1 calc R . . C14 C 0.2634(3) -0.1242(2) 1.04711(11) 0.0672(6) Uani 1 1 d . . . H14A H 0.2804 -0.0382 1.0674 0.101 Uiso 1 1 calc R . . H14B H 0.3375 -0.1380 1.0105 0.101 Uiso 1 1 calc R . . H14C H 0.2770 -0.1919 1.0816 0.101 Uiso 1 1 calc R . . C15 C -0.0238(3) -0.1050(2) 1.07436(10) 0.0656(6) Uani 1 1 d . . . H15A H -0.0079 -0.0174 1.0930 0.098 Uiso 1 1 calc R . . H15B H -0.0124 -0.1699 1.1104 0.098 Uiso 1 1 calc R . . H15C H -0.1274 -0.1110 1.0551 0.098 Uiso 1 1 calc R . . C16 C 0.1335(3) -0.11318(19) 0.88864(9) 0.0551(5) Uani 1 1 d . . . H16A H 0.2453 -0.1290 0.8936 0.066 Uiso 1 1 calc R . . H16B H 0.0821 -0.1989 0.8837 0.066 Uiso 1 1 calc R . . C17 C 0.1050(3) -0.0312(2) 0.82429(9) 0.0589(6) Uani 1 1 d . . . H17A H -0.0072 -0.0255 0.8162 0.071 Uiso 1 1 calc R . . H17B H 0.1515 -0.0766 0.7851 0.071 Uiso 1 1 calc R . . C18 C 0.1724(2) 0.1098(2) 0.82857(8) 0.0485(5) Uani 1 1 d . . . H18 H 0.2861 0.1017 0.8349 0.058 Uiso 1 1 calc R . . C19 C 0.1446(3) 0.1794(3) 0.75959(10) 0.0806(8) Uani 1 1 d . . . H19A H 0.1726 0.1204 0.7226 0.121 Uiso 1 1 calc R . . H19B H 0.2080 0.2583 0.7572 0.121 Uiso 1 1 calc R . . H19C H 0.0359 0.2032 0.7556 0.121 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 0.0419(6) 0.0358(6) 0.0313(6) -0.0010(4) 0.0025(5) -0.0035(5) O2 0.0559(7) 0.0381(6) 0.0331(6) 0.0010(5) 0.0009(5) 0.0011(6) C1 0.0344(9) 0.0375(9) 0.0372(9) -0.0005(7) -0.0011(7) -0.0017(7) C2 0.0337(8) 0.0423(9) 0.0367(8) -0.0034(7) -0.0024(7) -0.0030(8) C3 0.0547(11) 0.0434(10) 0.0428(10) -0.0027(8) -0.0039(9) -0.0028(9) C4 0.0663(14) 0.0513(11) 0.0568(12) -0.0168(9) -0.0005(10) -0.0017(10) C5 0.0647(14) 0.0718(14) 0.0407(10) -0.0178(10) -0.0008(10) -0.0056(11) C6 0.0687(14) 0.0714(14) 0.0344(9) 0.0029(9) 0.0000(9) -0.0029(12) C7 0.0568(12) 0.0481(10) 0.0411(9) -0.0009(8) -0.0002(9) -0.0001(10) C8 0.0827(15) 0.0516(11) 0.0415(10) 0.0095(9) 0.0013(11) 0.0095(11) C9 0.0440(10) 0.0449(9) 0.0336(9) 0.0029(7) 0.0041(7) -0.0018(8) C10 0.0336(8) 0.0469(9) 0.0336(8) 0.0006(7) 0.0016(7) 0.0012(8) C11 0.0338(8) 0.0371(8) 0.0331(8) -0.0019(7) 0.0008(7) 0.0012(7) C12 0.0402(9) 0.0388(9) 0.0434(9) -0.0036(7) -0.0010(8) -0.0014(7) C13 0.0622(12) 0.0325(9) 0.0506(10) -0.0007(8) 0.0010(9) -0.0011(9) C14 0.0770(14) 0.0623(14) 0.0622(13) 0.0095(11) -0.0149(11) 0.0141(12) C15 0.0834(16) 0.0547(12) 0.0587(12) 0.0090(11) 0.0183(11) -0.0050(12) C16 0.0739(14) 0.0426(10) 0.0489(10) -0.0122(8) -0.0018(10) 0.0001(11) C17 0.0729(14) 0.0608(12) 0.0429(10) -0.0178(9) 0.0024(10) 0.0005(11) C18 0.0503(10) 0.0586(11) 0.0365(9) -0.0052(8) 0.0059(8) -0.0017(10) C19 0.132(2) 0.0743(15) 0.0352(11) -0.0015(10) 0.0114(13) -0.0022(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4079(19) . ? O1 C11 1.4397(18) . ? O2 C1 1.3939(19) . ? O2 C9 1.4392(19) . ? C1 C2 1.505(2) . ? C2 C3 1.380(3) . ? C2 C7 1.384(2) . ? C3 C4 1.386(3) . ? C4 C5 1.362(3) . ? C5 C6 1.373(3) . ? C6 C7 1.386(3) . ? C8 C9 1.518(2) . ? C9 C10 1.537(2) . ? C10 C11 1.534(2) . ? C10 C18 1.545(2) . ? C11 C12 1.524(2) . ? C12 C16 1.530(2) . ? C12 C13 1.543(2) . ? C13 C15 1.521(3) . ? C13 C14 1.526(3) . ? C16 C17 1.513(3) . ? C17 C18 1.530(3) . ? C18 C19 1.526(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 C1 O1 C11 109.20(11) . . ? C1 O2 C9 112.33(12) . . ? O2 C1 O1 110.16(13) . . ? O2 C1 C2 109.66(13) . . ? O1 C1 C2 109.48(13) . . ? C3 C2 C7 118.44(16) . . ? C3 C2 C1 121.05(16) . . ? C7 C2 C1 120.40(16) . . ? C2 C3 C4 120.59(18) . . ? C5 C4 C3 120.61(18) . . ? C4 C5 C6 119.53(18) . . ? C5 C6 C7 120.37(19) . . ? C2 C7 C6 120.47(18) . . ? O2 C9 C8 103.16(14) . . ? O2 C9 C10 110.04(13) . . ? C8 C9 C10 115.85(15) . . ? C11 C10 C9 109.77(13) . . ? C11 C10 C18 107.73(14) . . ? C9 C10 C18 114.95(15) . . ? O1 C11 C12 108.58(12) . . ? O1 C11 C10 110.82(12) . . ? C12 C11 C10 112.90(13) . . ? C11 C12 C16 107.26(14) . . ? C11 C12 C13 115.67(14) . . ? C16 C12 C13 111.20(14) . . ? C15 C13 C14 111.00(17) . . ? C15 C13 C12 112.78(15) . . ? C14 C13 C12 113.49(16) . . ? C17 C16 C12 112.08(16) . . ? C16 C17 C18 113.46(16) . . ? C19 C18 C17 108.55(16) . . ? C19 C18 C10 116.36(17) . . ? C17 C18 C10 109.01(15) . . ? 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 O2 C1 O1 -65.71(17) . . . . ? C9 O2 C1 C2 173.73(13) . . . . ? C11 O1 C1 O2 66.58(15) . . . . ? C11 O1 C1 C2 -172.75(13) . . . . ? O2 C1 C2 C3 -22.7(2) . . . . ? O1 C1 C2 C3 -143.64(17) . . . . ? O2 C1 C2 C7 161.37(16) . . . . ? O1 C1 C2 C7 40.4(2) . . . . ? C7 C2 C3 C4 -0.2(3) . . . . ? C1 C2 C3 C4 -176.22(16) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C1 C2 C7 C6 176.21(18) . . . . ? C5 C6 C7 C2 -0.1(3) . . . . ? C1 O2 C9 C8 179.38(14) . . . . ? C1 O2 C9 C10 55.20(18) . . . . ? O2 C9 C10 C11 -46.58(19) . . . . ? C8 C9 C10 C11 -163.06(15) . . . . ? O2 C9 C10 C18 -168.18(14) . . . . ? C8 C9 C10 C18 75.3(2) . . . . ? C1 O1 C11 C12 176.52(13) . . . . ? C1 O1 C11 C10 -58.93(16) . . . . ? C9 C10 C11 O1 49.52(18) . . . . ? C18 C10 C11 O1 175.35(13) . . . . ? C9 C10 C11 C12 171.57(13) . . . . ? C18 C10 C11 C12 -62.59(18) . . . . ? O1 C11 C12 C16 -176.44(13) . . . . ? C10 C11 C12 C16 60.25(18) . . . . ? O1 C11 C12 C13 -51.73(18) . . . . ? C10 C11 C12 C13 -175.04(14) . . . . ? C11 C12 C13 C15 85.32(19) . . . . ? C16 C12 C13 C15 -152.03(18) . . . . ? C11 C12 C13 C14 -42.0(2) . . . . ? C16 C12 C13 C14 80.6(2) . . . . ? C11 C12 C16 C17 -54.7(2) . . . . ? C13 C12 C16 C17 177.97(16) . . . . ? C12 C16 C17 C18 55.1(2) . . . . ? C16 C17 C18 C19 176.79(18) . . . . ? C16 C17 C18 C10 -55.6(2) . . . . ? C11 C10 C18 C19 -179.84(17) . . . . ? C9 C10 C18 C19 -57.1(2) . . . . ? C11 C10 C18 C17 57.05(19) . . . . ? C9 C10 C18 C17 179.76(15) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.171 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.033 data_str0154_Compound_30 _database_code_CSD 216436 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H42 O4' _chemical_formula_weight 514.68 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.6743(7) _cell_length_b 16.4346(10) _cell_length_c 16.6813(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2926.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9940 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26059 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.33 _reflns_number_total 6887 _reflns_number_gt 5908 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(8) _refine_ls_number_reflns 6887 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.32379(9) 0.56017(7) 0.00712(6) 0.0535(2) Uani 1 1 d . . . O2 O 0.11248(9) 0.57868(6) 0.01045(6) 0.0490(2) Uani 1 1 d . . . O3 O 0.19957(10) 0.41654(6) 0.01927(6) 0.0536(2) Uani 1 1 d . . . O4 O 0.30473(9) 0.44746(6) 0.13393(6) 0.0515(2) Uani 1 1 d . . . C1 C 0.2454(3) 0.88622(12) -0.00699(15) 0.0971(7) Uani 1 1 d . . . H1A H 0.1756 0.9215 -0.0175 0.146 Uiso 1 1 calc R . . H1B H 0.3222 0.9156 -0.0149 0.146 Uiso 1 1 calc R . . H1C H 0.2412 0.8671 0.0473 0.146 Uiso 1 1 calc R . . C2 C 0.2471(2) 0.83880(13) -0.15014(12) 0.0805(6) Uani 1 1 d . . . H2A H 0.2541 0.7910 -0.1830 0.121 Uiso 1 1 calc R . . H2B H 0.3188 0.8730 -0.1586 0.121 Uiso 1 1 calc R . . H2C H 0.1724 0.8680 -0.1643 0.121 Uiso 1 1 calc R . . C3 C 0.24096(19) 0.81439(10) -0.06370(11) 0.0669(4) Uani 1 1 d . . . C4 C 0.30344(17) 0.73774(10) -0.03230(10) 0.0610(4) Uani 1 1 d . . . H4 H 0.3409 0.7422 0.0211 0.073 Uiso 1 1 calc R . . C5 C 0.16191(16) 0.74401(10) -0.03513(10) 0.0582(4) Uani 1 1 d . . . H5 H 0.1206 0.7518 0.0168 0.070 Uiso 1 1 calc R . . C6 C 0.10151(16) 0.68261(11) -0.08961(10) 0.0599(4) Uani 1 1 d . . . H6A H 0.1207 0.6959 -0.1449 0.072 Uiso 1 1 calc R . . H6B H 0.0113 0.6847 -0.0830 0.072 Uiso 1 1 calc R . . C7 C 0.14780(15) 0.59718(10) -0.07111(9) 0.0522(3) Uani 1 1 d . . . C8 C 0.29204(14) 0.59141(9) -0.06993(8) 0.0515(3) Uani 1 1 d . . . H8 H 0.3190 0.5524 -0.1109 0.062 Uiso 1 1 calc R . . C9 C 0.35681(16) 0.67218(11) -0.08487(12) 0.0642(4) Uani 1 1 d . . . H9A H 0.4457 0.6666 -0.0742 0.077 Uiso 1 1 calc R . . H9B H 0.3467 0.6874 -0.1407 0.077 Uiso 1 1 calc R . . C10 C 0.0888(2) 0.53462(12) -0.12661(10) 0.0742(5) Uani 1 1 d . . . H10A H 0.1156 0.4811 -0.1112 0.111 Uiso 1 1 calc R . . H10B H 0.1143 0.5452 -0.1808 0.111 Uiso 1 1 calc R . . H10C H -0.0008 0.5380 -0.1228 0.111 Uiso 1 1 calc R . . C11 C 0.21733(13) 0.55813(8) 0.05732(8) 0.0455(3) Uani 1 1 d . . . C12 C 0.23424(16) 0.61671(9) 0.12679(9) 0.0518(3) Uani 1 1 d . . . C13 C 0.13393(19) 0.66122(10) 0.15566(10) 0.0651(4) Uani 1 1 d . . . H13 H 0.0545 0.6540 0.1339 0.078 Uiso 1 1 calc R . . C14 C 0.1524(3) 0.71669(12) 0.21737(13) 0.0858(7) Uani 1 1 d . . . H14 H 0.0854 0.7475 0.2361 0.103 Uiso 1 1 calc R . . C15 C 0.2689(3) 0.72632(13) 0.25088(13) 0.0961(8) Uani 1 1 d . . . H15 H 0.2805 0.7630 0.2926 0.115 Uiso 1 1 calc R . . C16 C 0.3677(3) 0.68205(14) 0.22296(13) 0.0906(7) Uani 1 1 d . . . H16 H 0.4465 0.6888 0.2458 0.109 Uiso 1 1 calc R . . C17 C 0.3517(2) 0.62685(11) 0.16050(11) 0.0703(5) Uani 1 1 d . . . H17 H 0.4195 0.5970 0.1415 0.084 Uiso 1 1 calc R . . C18 C 0.3238(2) 0.12460(12) 0.10234(14) 0.0885(6) Uani 1 1 d . . . H18A H 0.3932 0.1547 0.0809 0.133 Uiso 1 1 calc R . . H18B H 0.3029 0.0809 0.0666 0.133 Uiso 1 1 calc R . . H18C H 0.3463 0.1027 0.1537 0.133 Uiso 1 1 calc R . . C19 C 0.0970(3) 0.13620(13) 0.13997(14) 0.0896(7) Uani 1 1 d . . . H19A H 0.1121 0.1136 0.1922 0.134 Uiso 1 1 calc R . . H19B H 0.0770 0.0932 0.1031 0.134 Uiso 1 1 calc R . . H19C H 0.0282 0.1738 0.1427 0.134 Uiso 1 1 calc R . . C20 C 0.21266(19) 0.18014(10) 0.11155(10) 0.0627(4) Uani 1 1 d . . . C21 C 0.18930(16) 0.25134(9) 0.05636(9) 0.0557(4) Uani 1 1 d . . . H21 H 0.1009 0.2622 0.0447 0.067 Uiso 1 1 calc R . . C22 C 0.22778(17) 0.26607(9) 0.14232(9) 0.0559(4) Uani 1 1 d . . . H22 H 0.1618 0.2857 0.1783 0.067 Uiso 1 1 calc R . . C23 C 0.35418(18) 0.30535(10) 0.15199(11) 0.0664(5) Uani 1 1 d . . . H23A H 0.4185 0.2658 0.1389 0.080 Uiso 1 1 calc R . . H23B H 0.3652 0.3208 0.2077 0.080 Uiso 1 1 calc R . . C24 C 0.37232(14) 0.38067(10) 0.09927(10) 0.0545(4) Uani 1 1 d . . . C25 C 0.31360(15) 0.37086(10) 0.01590(9) 0.0555(4) Uani 1 1 d . . . H25 H 0.3694 0.3934 -0.0251 0.067 Uiso 1 1 calc R . . C26 C 0.27960(18) 0.28331(10) -0.00465(10) 0.0622(4) Uani 1 1 d . . . H26A H 0.2420 0.2811 -0.0575 0.075 Uiso 1 1 calc R . . H26B H 0.3546 0.2500 -0.0051 0.075 Uiso 1 1 calc R . . C27 C 0.50903(16) 0.40506(14) 0.09538(16) 0.0852(6) Uani 1 1 d . . . H27A H 0.5167 0.4558 0.0673 0.128 Uiso 1 1 calc R . . H27B H 0.5557 0.3638 0.0676 0.128 Uiso 1 1 calc R . . H27C H 0.5413 0.4110 0.1488 0.128 Uiso 1 1 calc R . . C28 C 0.20019(12) 0.46803(8) 0.08672(8) 0.0446(3) Uani 1 1 d . . . C29 C 0.07941(13) 0.45634(8) 0.13346(8) 0.0462(3) Uani 1 1 d . . . C30 C -0.03027(15) 0.43920(11) 0.09320(11) 0.0632(4) Uani 1 1 d . . . H30 H -0.0303 0.4357 0.0376 0.076 Uiso 1 1 calc R . . C31 C -0.14009(18) 0.42723(13) 0.13528(14) 0.0789(5) Uani 1 1 d . . . H31 H -0.2140 0.4159 0.1079 0.095 Uiso 1 1 calc R . . C32 C -0.14038(18) 0.43205(12) 0.21748(14) 0.0758(5) Uani 1 1 d . . . H32 H -0.2142 0.4235 0.2458 0.091 Uiso 1 1 calc R . . C33 C -0.03226(18) 0.44940(11) 0.25748(11) 0.0694(5) Uani 1 1 d . . . H33 H -0.0327 0.4531 0.3131 0.083 Uiso 1 1 calc R . . C34 C 0.07838(16) 0.46162(10) 0.21569(9) 0.0578(4) Uani 1 1 d . . . H34 H 0.1519 0.4734 0.2433 0.069 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 0.0448(5) 0.0664(6) 0.0492(5) 0.0022(5) 0.0032(4) -0.0030(4) O2 0.0445(5) 0.0544(6) 0.0482(5) 0.0096(4) 0.0002(4) -0.0023(4) O3 0.0601(6) 0.0524(6) 0.0482(5) -0.0087(4) -0.0067(5) 0.0044(5) O4 0.0509(5) 0.0538(6) 0.0499(5) -0.0077(4) -0.0079(4) 0.0095(4) C1 0.138(2) 0.0543(10) 0.0986(15) -0.0023(11) -0.0053(15) -0.0004(12) C2 0.0850(13) 0.0744(12) 0.0822(13) 0.0255(10) 0.0063(11) -0.0112(11) C3 0.0771(11) 0.0507(8) 0.0728(10) 0.0082(8) -0.0003(9) -0.0056(8) C4 0.0654(10) 0.0506(8) 0.0669(9) 0.0034(7) -0.0067(8) -0.0097(7) C5 0.0661(10) 0.0519(8) 0.0567(8) 0.0089(7) 0.0080(7) 0.0025(7) C6 0.0534(8) 0.0668(10) 0.0596(9) 0.0173(8) -0.0042(7) -0.0052(7) C7 0.0550(8) 0.0573(8) 0.0444(7) 0.0054(6) -0.0020(6) -0.0123(7) C8 0.0560(8) 0.0535(8) 0.0450(7) -0.0030(6) 0.0071(6) -0.0021(7) C9 0.0540(9) 0.0626(10) 0.0760(11) 0.0065(9) 0.0119(8) -0.0094(8) C10 0.0852(12) 0.0780(12) 0.0594(9) -0.0011(9) -0.0116(9) -0.0242(10) C11 0.0413(6) 0.0481(7) 0.0472(7) 0.0001(6) 0.0008(5) -0.0014(6) C12 0.0638(9) 0.0445(7) 0.0469(7) 0.0017(6) 0.0031(7) -0.0065(7) C13 0.0780(11) 0.0553(9) 0.0621(10) -0.0022(7) 0.0173(9) -0.0018(8) C14 0.1251(19) 0.0634(11) 0.0688(12) -0.0117(9) 0.0292(13) -0.0014(12) C15 0.163(2) 0.0660(12) 0.0595(11) -0.0164(9) -0.0052(14) -0.0097(15) C16 0.1214(19) 0.0733(12) 0.0770(13) -0.0142(11) -0.0304(13) -0.0152(13) C17 0.0797(12) 0.0641(10) 0.0672(10) -0.0107(8) -0.0158(9) -0.0026(9) C18 0.1155(18) 0.0592(10) 0.0907(13) -0.0091(10) -0.0034(13) 0.0254(11) C19 0.1140(18) 0.0703(12) 0.0846(13) 0.0017(11) 0.0011(13) -0.0265(12) C20 0.0818(11) 0.0487(8) 0.0575(9) -0.0044(7) -0.0016(8) 0.0022(8) C21 0.0625(9) 0.0509(8) 0.0538(8) -0.0079(6) -0.0036(7) 0.0012(7) C22 0.0708(10) 0.0505(8) 0.0464(7) -0.0037(6) 0.0020(7) 0.0066(7) C23 0.0772(11) 0.0564(9) 0.0655(10) -0.0032(8) -0.0244(9) 0.0080(8) C24 0.0448(7) 0.0548(8) 0.0640(9) -0.0085(7) -0.0011(7) 0.0060(6) C25 0.0594(9) 0.0549(8) 0.0522(8) -0.0045(6) 0.0104(7) 0.0035(7) C26 0.0812(11) 0.0567(8) 0.0486(8) -0.0104(7) 0.0056(8) 0.0071(8) C27 0.0461(9) 0.0968(15) 0.1128(16) -0.0289(13) 0.0050(10) -0.0027(9) C28 0.0466(7) 0.0451(7) 0.0420(6) -0.0030(5) -0.0047(6) 0.0011(6) C29 0.0493(7) 0.0372(6) 0.0520(7) 0.0043(6) -0.0004(6) 0.0013(6) C30 0.0549(8) 0.0697(10) 0.0650(9) 0.0089(8) -0.0046(7) -0.0118(8) C31 0.0519(9) 0.0840(13) 0.1009(15) 0.0163(12) -0.0018(9) -0.0132(9) C32 0.0635(10) 0.0642(10) 0.0998(14) 0.0203(10) 0.0260(10) 0.0028(9) C33 0.0788(12) 0.0638(10) 0.0656(10) 0.0091(8) 0.0185(9) 0.0115(9) C34 0.0584(9) 0.0615(9) 0.0535(8) 0.0015(7) 0.0024(7) 0.0068(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.4120(17) . ? O1 C8 1.4248(18) . ? O2 C11 1.4064(17) . ? O2 C7 1.4442(18) . ? O3 C28 1.4079(16) . ? O3 C25 1.4312(19) . ? O4 C28 1.4071(16) . ? O4 C24 1.4352(18) . ? C1 C3 1.513(3) . ? C2 C3 1.498(3) . ? C3 C5 1.509(2) . ? C3 C4 1.519(2) . ? C4 C9 1.501(2) . ? C4 C5 1.515(2) . ? C5 C6 1.503(2) . ? C6 C7 1.520(2) . ? C7 C10 1.520(2) . ? C7 C8 1.543(2) . ? C8 C9 1.517(2) . ? C11 C12 1.517(2) . ? C11 C28 1.5704(19) . ? C12 C17 1.384(3) . ? C12 C13 1.383(2) . ? C13 C14 1.389(3) . ? C14 C15 1.373(4) . ? C15 C16 1.363(4) . ? C16 C17 1.392(3) . ? C18 C20 1.505(3) . ? C19 C20 1.507(3) . ? C20 C21 1.510(2) . ? C20 C22 1.511(2) . ? C21 C26 1.497(2) . ? C21 C22 1.511(2) . ? C22 C23 1.504(3) . ? C23 C24 1.531(2) . ? C24 C27 1.515(2) . ? C24 C25 1.534(2) . ? C25 C26 1.523(2) . ? C28 C29 1.5189(19) . ? C29 C34 1.374(2) . ? C29 C30 1.379(2) . ? C30 C31 1.380(3) . ? C31 C32 1.373(3) . ? C32 C33 1.363(3) . ? C33 C34 1.386(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 O1 C8 110.61(10) . . ? C11 O2 C7 111.50(10) . . ? C28 O3 C25 110.04(10) . . ? C28 O4 C24 110.91(11) . . ? C2 C3 C5 122.25(17) . . ? C2 C3 C1 113.04(17) . . ? C5 C3 C1 114.72(17) . . ? C2 C3 C4 122.33(18) . . ? C5 C3 C4 60.05(11) . . ? C1 C3 C4 114.69(17) . . ? C9 C4 C5 114.14(14) . . ? C9 C4 C3 124.09(15) . . ? C5 C4 C3 59.66(11) . . ? C6 C5 C3 124.30(15) . . ? C6 C5 C4 113.64(14) . . ? C3 C5 C4 60.29(12) . . ? C5 C6 C7 110.97(13) . . ? O2 C7 C6 107.51(13) . . ? O2 C7 C10 108.85(12) . . ? C6 C7 C10 111.49(14) . . ? O2 C7 C8 103.62(12) . . ? C6 C7 C8 112.57(13) . . ? C10 C7 C8 112.33(15) . . ? O1 C8 C9 110.80(13) . . ? O1 C8 C7 105.73(11) . . ? C9 C8 C7 113.51(14) . . ? C4 C9 C8 111.04(13) . . ? O2 C11 O1 107.76(11) . . ? O2 C11 C12 111.52(12) . . ? O1 C11 C12 110.01(11) . . ? O2 C11 C28 107.90(11) . . ? O1 C11 C28 107.54(11) . . ? C12 C11 C28 111.93(11) . . ? C17 C12 C13 119.73(15) . . ? C17 C12 C11 119.64(15) . . ? C13 C12 C11 120.62(15) . . ? C12 C13 C14 119.7(2) . . ? C15 C14 C13 120.4(2) . . ? C16 C15 C14 120.01(19) . . ? C15 C16 C17 120.6(2) . . ? C12 C17 C16 119.6(2) . . ? C18 C20 C19 112.80(17) . . ? C18 C20 C21 122.55(17) . . ? C19 C20 C21 115.34(18) . . ? C18 C20 C22 121.15(18) . . ? C19 C20 C22 115.37(16) . . ? C21 C20 C22 60.03(10) . . ? C26 C21 C20 125.47(16) . . ? C26 C21 C22 114.45(14) . . ? C20 C21 C22 60.04(10) . . ? C23 C22 C20 122.22(15) . . ? C23 C22 C21 114.48(14) . . ? C20 C22 C21 59.93(10) . . ? C22 C23 C24 113.50(13) . . ? O4 C24 C27 107.40(14) . . ? O4 C24 C23 108.87(13) . . ? C27 C24 C23 111.13(16) . . ? O4 C24 C25 103.90(12) . . ? C27 C24 C25 112.50(16) . . ? C23 C24 C25 112.59(13) . . ? O3 C25 C26 107.56(13) . . ? O3 C25 C24 104.88(11) . . ? C26 C25 C24 113.63(14) . . ? C21 C26 C25 109.39(13) . . ? O4 C28 O3 107.85(10) . . ? O4 C28 C29 110.82(10) . . ? O3 C28 C29 109.28(11) . . ? O4 C28 C11 108.00(11) . . ? O3 C28 C11 108.52(11) . . ? C29 C28 C11 112.24(11) . . ? C34 C29 C30 119.49(15) . . ? C34 C29 C28 120.74(13) . . ? C30 C29 C28 119.77(13) . . ? C29 C30 C31 120.16(17) . . ? C32 C31 C30 120.09(18) . . ? C33 C32 C31 119.92(17) . . ? C32 C33 C34 120.36(17) . . ? C29 C34 C33 119.98(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 C2 C3 C4 C9 -11.2(3) . . . . ? C5 C3 C4 C9 100.14(18) . . . . ? C1 C3 C4 C9 -154.42(18) . . . . ? C2 C3 C4 C5 -111.4(2) . . . . ? C1 C3 C4 C5 105.44(19) . . . . ? C2 C3 C5 C6 11.7(3) . . . . ? C1 C3 C5 C6 154.85(18) . . . . ? C4 C3 C5 C6 -99.76(18) . . . . ? C2 C3 C5 C4 111.5(2) . . . . ? C1 C3 C5 C4 -105.39(19) . . . . ? C9 C4 C5 C6 0.6(2) . . . . ? C3 C4 C5 C6 117.29(16) . . . . ? C9 C4 C5 C3 -116.71(17) . . . . ? C3 C5 C6 C7 120.26(18) . . . . ? C4 C5 C6 C7 51.13(18) . . . . ? C11 O2 C7 C6 -122.98(13) . . . . ? C11 O2 C7 C10 116.11(15) . . . . ? C11 O2 C7 C8 -3.61(15) . . . . ? C5 C6 C7 O2 61.58(16) . . . . ? C5 C6 C7 C10 -179.19(14) . . . . ? C5 C6 C7 C8 -51.91(18) . . . . ? C11 O1 C8 C9 114.29(14) . . . . ? C11 O1 C8 C7 -9.10(15) . . . . ? O2 C7 C8 O1 7.55(15) . . . . ? C6 C7 C8 O1 123.40(13) . . . . ? C10 C7 C8 O1 -109.77(14) . . . . ? O2 C7 C8 C9 -114.11(14) . . . . ? C6 C7 C8 C9 1.74(19) . . . . ? C10 C7 C8 C9 128.58(15) . . . . ? C5 C4 C9 C8 -51.0(2) . . . . ? C3 C4 C9 C8 -119.54(18) . . . . ? O1 C8 C9 C4 -69.51(17) . . . . ? C7 C8 C9 C4 49.27(19) . . . . ? C7 O2 C11 O1 -1.77(15) . . . . ? C7 O2 C11 C12 119.06(13) . . . . ? C7 O2 C11 C28 -117.62(12) . . . . ? C8 O1 C11 O2 7.04(15) . . . . ? C8 O1 C11 C12 -114.74(13) . . . . ? C8 O1 C11 C28 123.12(11) . . . . ? O2 C11 C12 C17 -155.60(14) . . . . ? O1 C11 C12 C17 -36.09(18) . . . . ? C28 C11 C12 C17 83.41(17) . . . . ? O2 C11 C12 C13 23.12(19) . . . . ? O1 C11 C12 C13 142.63(14) . . . . ? C28 C11 C12 C13 -97.88(16) . . . . ? C17 C12 C13 C14 1.1(3) . . . . ? C11 C12 C13 C14 -177.66(15) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C13 C12 C17 C16 -0.3(3) . . . . ? C11 C12 C17 C16 178.47(17) . . . . ? C15 C16 C17 C12 -0.3(3) . . . . ? C18 C20 C21 C26 -9.8(3) . . . . ? C19 C20 C21 C26 -153.96(16) . . . . ? C22 C20 C21 C26 100.13(17) . . . . ? C18 C20 C21 C22 -109.9(2) . . . . ? C19 C20 C21 C22 105.92(17) . . . . ? C18 C20 C22 C23 10.6(3) . . . . ? C19 C20 C22 C23 152.55(18) . . . . ? C21 C20 C22 C23 -101.60(17) . . . . ? C18 C20 C22 C21 112.2(2) . . . . ? C19 C20 C22 C21 -105.86(19) . . . . ? C26 C21 C22 C23 -3.86(19) . . . . ? C20 C21 C22 C23 114.42(17) . . . . ? C26 C21 C22 C20 -118.27(17) . . . . ? C20 C22 C23 C24 117.77(17) . . . . ? C21 C22 C23 C24 49.10(19) . . . . ? C28 O4 C24 C27 129.73(16) . . . . ? C28 O4 C24 C23 -109.85(14) . . . . ? C28 O4 C24 C25 10.34(15) . . . . ? C22 C23 C24 O4 76.10(17) . . . . ? C22 C23 C24 C27 -165.80(16) . . . . ? C22 C23 C24 C25 -38.56(19) . . . . ? C28 O3 C25 C26 136.11(12) . . . . ? C28 O3 C25 C24 14.85(15) . . . . ? O4 C24 C25 O3 -14.99(15) . . . . ? C27 C24 C25 O3 -130.84(15) . . . . ? C23 C24 C25 O3 102.65(15) . . . . ? O4 C24 C25 C26 -132.18(14) . . . . ? C27 C24 C25 C26 111.96(17) . . . . ? C23 C24 C25 C26 -14.54(19) . . . . ? C20 C21 C26 C25 -118.20(16) . . . . ? C22 C21 C26 C25 -48.66(19) . . . . ? O3 C25 C26 C21 -56.96(17) . . . . ? C24 C25 C26 C21 58.67(18) . . . . ? C24 O4 C28 O3 -1.58(15) . . . . ? C24 O4 C28 C29 118.00(13) . . . . ? C24 O4 C28 C11 -118.68(12) . . . . ? C25 O3 C28 O4 -8.83(15) . . . . ? C25 O3 C28 C29 -129.37(12) . . . . ? C25 O3 C28 C11 107.94(12) . . . . ? O2 C11 C28 O4 -179.74(10) . . . . ? O1 C11 C28 O4 64.27(13) . . . . ? C12 C11 C28 O4 -56.67(14) . . . . ? O2 C11 C28 O3 63.59(13) . . . . ? O1 C11 C28 O3 -52.40(13) . . . . ? C12 C11 C28 O3 -173.34(11) . . . . ? O2 C11 C28 C29 -57.29(14) . . . . ? O1 C11 C28 C29 -173.28(11) . . . . ? C12 C11 C28 C29 65.78(15) . . . . ? O4 C28 C29 C34 26.54(18) . . . . ? O3 C28 C29 C34 145.26(13) . . . . ? C11 C28 C29 C34 -94.30(15) . . . . ? O4 C28 C29 C30 -152.62(13) . . . . ? O3 C28 C29 C30 -33.90(18) . . . . ? C11 C28 C29 C30 86.54(16) . . . . ? C34 C29 C30 C31 -0.2(3) . . . . ? C28 C29 C30 C31 179.00(16) . . . . ? C29 C30 C31 C32 -0.3(3) . . . . ? C30 C31 C32 C33 0.6(3) . . . . ? C31 C32 C33 C34 -0.5(3) . . . . ? C30 C29 C34 C33 0.3(2) . . . . ? C28 C29 C34 C33 -178.89(15) . . . . ? C32 C33 C34 C29 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.134 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.036 data_str0165_Compound_56 _database_code_CSD 216437 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 O2' _chemical_formula_weight 288.41 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.804(3) _cell_length_b 10.274(3) _cell_length_c 18.428(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1666.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9648 _exptl_absorpt_correction_T_max 0.9986 _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14443 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3899 _reflns_number_gt 2927 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.1(15) _refine_ls_number_reflns 3899 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 O1 O 0.15357(17) 0.16319(12) 1.03009(7) 0.0232(3) Uani 1 1 d . . . O2 O 0.11113(18) 0.36569(12) 0.98012(7) 0.0255(4) Uani 1 1 d . . . C1 C 0.1945(2) 0.29512(18) 1.03172(11) 0.0231(5) Uani 1 1 d . . . H1 H 0.3054 0.3037 1.0210 0.028 Uiso 1 1 calc R . . C2 C 0.1615(2) 0.35216(19) 1.10605(11) 0.0240(5) Uani 1 1 d . . . C3 C 0.1508(3) 0.4863(2) 1.11330(12) 0.0298(5) Uani 1 1 d . . . H3 H 0.1586 0.5405 1.0717 0.036 Uiso 1 1 calc R . . C4 C 0.1287(3) 0.5414(2) 1.18130(12) 0.0359(6) Uani 1 1 d . . . H4 H 0.1227 0.6333 1.1861 0.043 Uiso 1 1 calc R . . C5 C 0.1156(3) 0.4637(2) 1.24170(12) 0.0392(6) Uani 1 1 d . . . H5 H 0.0993 0.5014 1.2881 0.047 Uiso 1 1 calc R . . C6 C 0.1262(3) 0.3299(2) 1.23427(12) 0.0384(6) Uani 1 1 d . . . H6 H 0.1180 0.2758 1.2759 0.046 Uiso 1 1 calc R . . C7 C 0.1488(3) 0.2744(2) 1.16671(11) 0.0306(5) Uani 1 1 d . . . H7 H 0.1556 0.1825 1.1621 0.037 Uiso 1 1 calc R . . C8 C 0.0462(3) 0.4146(2) 0.86171(12) 0.0386(6) Uani 1 1 d . . . H8A H -0.0604 0.3900 0.8686 0.058 Uiso 1 1 calc R . . H8B H 0.0732 0.4060 0.8103 0.058 Uiso 1 1 calc R . . H8C H 0.0610 0.5050 0.8772 0.058 Uiso 1 1 calc R . . C9 C 0.1463(3) 0.32625(18) 0.90653(10) 0.0247(5) Uani 1 1 d . . . H9 H 0.2550 0.3473 0.8961 0.030 Uiso 1 1 calc R . . C10 C 0.1223(2) 0.17812(18) 0.89768(10) 0.0211(4) Uani 1 1 d . . . H10 H 0.0108 0.1600 0.8996 0.025 Uiso 1 1 calc R . . C11 C 0.1986(2) 0.10725(19) 0.96155(10) 0.0218(4) Uani 1 1 d . . . H11 H 0.3107 0.1203 0.9566 0.026 Uiso 1 1 calc R . . C12 C 0.1700(2) -0.03978(19) 0.96391(11) 0.0258(5) Uani 1 1 d . . . H12 H 0.2343 -0.0756 1.0040 0.031 Uiso 1 1 calc R . . C13 C 0.0040(3) -0.0787(2) 0.98074(12) 0.0306(5) Uani 1 1 d . . . H13 H -0.0639 -0.0137 0.9567 0.037 Uiso 1 1 calc R . . C14 C -0.0400(3) -0.2141(2) 0.95222(14) 0.0440(7) Uani 1 1 d . . . H14A H 0.0285 -0.2795 0.9728 0.066 Uiso 1 1 calc R . . H14B H -0.0319 -0.2152 0.8992 0.066 Uiso 1 1 calc R . . H14C H -0.1448 -0.2338 0.9665 0.066 Uiso 1 1 calc R . . C15 C -0.0298(3) -0.0756(2) 1.06161(13) 0.0468(7) Uani 1 1 d . . . H15A H -0.1370 -0.0965 1.0697 0.070 Uiso 1 1 calc R . . H15B H -0.0080 0.0115 1.0807 0.070 Uiso 1 1 calc R . . H15C H 0.0340 -0.1397 1.0865 0.070 Uiso 1 1 calc R . . C16 C 0.2340(3) -0.0935(2) 0.89292(12) 0.0323(5) Uani 1 1 d . . . H16A H 0.3454 -0.0805 0.8921 0.039 Uiso 1 1 calc R . . H16B H 0.2140 -0.1882 0.8904 0.039 Uiso 1 1 calc R . . C17 C 0.1638(3) -0.0274(2) 0.82687(11) 0.0322(5) Uani 1 1 d . . . H17A H 0.0538 -0.0470 0.8256 0.039 Uiso 1 1 calc R . . H17B H 0.2100 -0.0642 0.7824 0.039 Uiso 1 1 calc R . . C18 C 0.1857(3) 0.1206(2) 0.82657(11) 0.0287(5) Uani 1 1 d . . . H18 H 0.2974 0.1381 0.8255 0.034 Uiso 1 1 calc R . . C19 C 0.1178(3) 0.1748(2) 0.75641(11) 0.0425(7) Uani 1 1 d . . . H19A H 0.1532 0.1229 0.7151 0.064 Uiso 1 1 calc R . . H19B H 0.1499 0.2654 0.7501 0.064 Uiso 1 1 calc R . . H19C H 0.0067 0.1708 0.7590 0.064 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 0.0296(8) 0.0205(7) 0.0194(7) -0.0009(6) 0.0003(7) -0.0002(6) O2 0.0330(9) 0.0243(7) 0.0191(7) 0.0006(6) -0.0043(7) 0.0021(6) C1 0.0219(11) 0.0243(11) 0.0230(10) -0.0012(8) -0.0031(9) 0.0006(9) C2 0.0172(10) 0.0308(11) 0.0241(11) -0.0053(9) -0.0002(10) 0.0006(9) C3 0.0301(13) 0.0298(11) 0.0296(11) -0.0020(9) -0.0001(10) -0.0012(10) C4 0.0358(15) 0.0363(13) 0.0355(13) -0.0134(10) -0.0030(12) 0.0000(11) C5 0.0376(14) 0.0542(16) 0.0257(12) -0.0150(11) -0.0029(12) 0.0027(13) C6 0.0403(15) 0.0505(16) 0.0242(12) -0.0007(10) -0.0026(11) -0.0007(13) C7 0.0322(14) 0.0334(12) 0.0262(11) 0.0006(9) -0.0022(10) 0.0016(11) C8 0.0587(17) 0.0284(11) 0.0286(13) 0.0042(10) -0.0080(11) 0.0036(12) C9 0.0323(13) 0.0218(10) 0.0200(11) 0.0011(8) 0.0003(9) -0.0067(10) C10 0.0192(10) 0.0256(10) 0.0184(10) 0.0002(8) 0.0000(9) -0.0042(9) C11 0.0194(10) 0.0269(11) 0.0192(10) -0.0015(8) 0.0004(8) 0.0040(9) C12 0.0303(12) 0.0236(10) 0.0235(11) 0.0006(8) -0.0016(10) 0.0081(9) C13 0.0374(13) 0.0188(10) 0.0356(13) 0.0036(9) 0.0028(11) -0.0011(10) C14 0.0597(18) 0.0261(12) 0.0462(15) 0.0025(11) 0.0050(13) -0.0128(13) C15 0.0623(18) 0.0337(13) 0.0445(15) 0.0003(12) 0.0233(14) -0.0074(14) C16 0.0371(13) 0.0281(11) 0.0318(12) -0.0041(10) 0.0053(11) 0.0084(11) C17 0.0440(15) 0.0283(11) 0.0244(11) -0.0074(9) 0.0058(10) 0.0032(11) C18 0.0320(13) 0.0323(12) 0.0219(11) -0.0027(9) 0.0056(10) -0.0069(10) C19 0.073(2) 0.0360(13) 0.0185(11) -0.0008(9) 0.0003(13) -0.0066(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.403(2) . ? O1 C11 1.443(2) . ? O2 C1 1.403(2) . ? O2 C9 1.449(2) . ? C1 C2 1.518(3) . ? C2 C7 1.378(3) . ? C2 C3 1.388(3) . ? C3 C4 1.389(3) . ? C4 C5 1.375(3) . ? C5 C6 1.385(3) . ? C6 C7 1.384(3) . ? C8 C9 1.511(3) . ? C9 C10 1.545(3) . ? C10 C11 1.538(3) . ? C10 C18 1.542(3) . ? C11 C12 1.532(3) . ? C12 C16 1.527(3) . ? C12 C13 1.547(3) . ? C13 C15 1.520(3) . ? C13 C14 1.536(3) . ? C16 C17 1.524(3) . ? C17 C18 1.532(3) . ? C18 C19 1.530(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 C1 O1 C11 109.45(15) . . ? C1 O2 C9 112.21(15) . . ? O1 C1 O2 110.50(16) . . ? O1 C1 C2 110.07(17) . . ? O2 C1 C2 108.17(16) . . ? C7 C2 C3 119.5(2) . . ? C7 C2 C1 121.58(18) . . ? C3 C2 C1 118.89(19) . . ? C2 C3 C4 120.1(2) . . ? C5 C4 C3 120.4(2) . . ? C4 C5 C6 119.4(2) . . ? C5 C6 C7 120.5(2) . . ? C2 C7 C6 120.2(2) . . ? O2 C9 C8 102.66(17) . . ? O2 C9 C10 110.19(15) . . ? C8 C9 C10 117.04(18) . . ? C11 C10 C18 108.10(16) . . ? C11 C10 C9 109.02(16) . . ? C18 C10 C9 114.72(16) . . ? O1 C11 C12 108.82(16) . . ? O1 C11 C10 111.16(15) . . ? C12 C11 C10 114.63(16) . . ? C16 C12 C11 105.74(17) . . ? C16 C12 C13 115.24(18) . . ? C11 C12 C13 114.59(17) . . ? C15 C13 C14 107.78(18) . . ? C15 C13 C12 112.1(2) . . ? C14 C13 C12 113.8(2) . . ? C17 C16 C12 111.96(17) . . ? C16 C17 C18 113.19(18) . . ? C19 C18 C17 108.37(18) . . ? C19 C18 C10 115.93(19) . . ? C17 C18 C10 109.39(17) . . ? 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 C11 O1 C1 O2 65.9(2) . . . . ? C11 O1 C1 C2 -174.65(15) . . . . ? C9 O2 C1 O1 -64.9(2) . . . . ? C9 O2 C1 C2 174.55(16) . . . . ? O1 C1 C2 C7 21.8(3) . . . . ? O2 C1 C2 C7 142.6(2) . . . . ? O1 C1 C2 C3 -161.17(19) . . . . ? O2 C1 C2 C3 -40.3(3) . . . . ? C7 C2 C3 C4 0.5(4) . . . . ? C1 C2 C3 C4 -176.6(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? C3 C2 C7 C6 -0.3(4) . . . . ? C1 C2 C7 C6 176.7(2) . . . . ? C5 C6 C7 C2 0.3(4) . . . . ? C1 O2 C9 C8 -179.48(17) . . . . ? C1 O2 C9 C10 55.1(2) . . . . ? O2 C9 C10 C11 -47.2(2) . . . . ? C8 C9 C10 C11 -163.93(19) . . . . ? O2 C9 C10 C18 -168.56(17) . . . . ? C8 C9 C10 C18 74.7(3) . . . . ? C1 O1 C11 C12 173.54(16) . . . . ? C1 O1 C11 C10 -59.3(2) . . . . ? C18 C10 C11 O1 175.47(15) . . . . ? C9 C10 C11 O1 50.2(2) . . . . ? C18 C10 C11 C12 -60.6(2) . . . . ? C9 C10 C11 C12 174.08(17) . . . . ? O1 C11 C12 C16 -174.77(16) . . . . ? C10 C11 C12 C16 60.1(2) . . . . ? O1 C11 C12 C13 57.2(2) . . . . ? C10 C11 C12 C13 -68.0(2) . . . . ? C16 C12 C13 C15 154.94(19) . . . . ? C11 C12 C13 C15 -82.0(2) . . . . ? C16 C12 C13 C14 32.3(3) . . . . ? C11 C12 C13 C14 155.35(19) . . . . ? C11 C12 C16 C17 -56.2(2) . . . . ? C13 C12 C16 C17 71.5(2) . . . . ? C12 C16 C17 C18 57.6(3) . . . . ? C16 C17 C18 C19 177.32(19) . . . . ? C16 C17 C18 C10 -55.4(3) . . . . ? C11 C10 C18 C19 177.37(18) . . . . ? C9 C10 C18 C19 -60.8(3) . . . . ? C11 C10 C18 C17 54.5(2) . . . . ? C9 C10 C18 C17 176.36(19) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.041