# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Richard Hsung' 'Kevin P. Cole' _publ_contact_author_name 'Richard Hsung' _publ_contact_author_address ; Department of Chemistry University of Minnesota 207 Pleasant St. SE Minneapolis MN 55455-0431 UNITED STATES OF AMERICA ; _publ_contact_author_email HSUNG@CHEM.UMN.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Unique Structural Topology and Reactivities of the ABD Tricycle in Phomactin A. ; data_05078a _database_code_depnum_ccdc_archive 'CCDC 280698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 05078a _chemical_melting_point ? _chemical_formula_moiety 'C19 H26 O3' _chemical_formula_sum 'C19 H26 O3' _chemical_formula_weight 302.40 _chemical_absolute_configuration unk 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 8.8438(7) _cell_length_b 8.9335(7) _cell_length_c 20.8095(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1644.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2657 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9723 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details 'K Cole / Prof. R. Hsung' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12713 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2177 _reflns_number_gt 2086 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0436P)^2^+0.3038P] 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 riding _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 -1.4(11) _refine_ls_number_reflns 2177 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.68811(14) 0.42712(18) 0.59110(6) 0.0418(3) Uani 1 1 d . . . O2 O 0.23450(12) 0.34320(12) 0.70356(5) 0.0245(2) Uani 1 1 d . . . O3 O 0.02211(16) 0.00385(15) 0.60975(6) 0.0411(3) Uani 1 1 d . . . C1 C 0.30469(18) 0.25965(16) 0.75724(7) 0.0259(3) Uani 1 1 d . . . C2 C 0.46151(18) 0.20879(19) 0.74002(8) 0.0300(3) Uani 1 1 d . . . H2A H 0.5069 0.1306 0.7642 0.036 Uiso 1 1 calc R . . C3 C 0.53851(17) 0.26990(18) 0.69198(7) 0.0279(3) Uani 1 1 d . . . H3A H 0.6413 0.2432 0.6854 0.033 Uiso 1 1 calc R . . C4 C 0.46656(17) 0.37782(16) 0.64909(7) 0.0225(3) Uani 1 1 d . . . C5 C 0.55238(18) 0.44971(19) 0.59782(7) 0.0268(3) Uani 1 1 d . . . C6 C 0.46740(19) 0.55546(18) 0.55475(7) 0.0304(3) Uani 1 1 d . . . H6A H 0.5185 0.5596 0.5125 0.036 Uiso 1 1 calc R . . H6B H 0.4707 0.6571 0.5736 0.036 Uiso 1 1 calc R . . C7 C 0.30231(19) 0.51010(19) 0.54478(7) 0.0280(3) Uani 1 1 d . . . H7A H 0.3031 0.4096 0.5236 0.034 Uiso 1 1 calc R . . C8 C 0.21787(17) 0.49175(17) 0.60959(7) 0.0236(3) Uani 1 1 d . . . C9 C 0.31523(17) 0.40136(15) 0.65512(6) 0.0207(3) Uani 1 1 d . . . C10 C 0.06137(18) 0.4172(2) 0.60001(8) 0.0297(3) Uani 1 1 d . . . H10A H 0.0153 0.4047 0.6430 0.036 Uiso 1 1 calc R . . H10B H -0.0029 0.4889 0.5761 0.036 Uiso 1 1 calc R . . C11 C 0.05077(19) 0.26515(19) 0.56529(8) 0.0322(4) Uani 1 1 d . . . H11A H -0.0575 0.2419 0.5585 0.039 Uiso 1 1 calc R . . H11B H 0.0976 0.2761 0.5223 0.039 Uiso 1 1 calc R . . C12 C 0.12394(19) 0.13117(19) 0.59861(8) 0.0302(3) Uani 1 1 d . . . C13 C 0.0714(2) 0.09497(19) 0.66348(8) 0.0339(4) Uani 1 1 d . . . H13A H -0.0081 0.1646 0.6800 0.041 Uiso 1 1 calc R . . C14 C 0.1646(2) 0.0227(2) 0.71573(8) 0.0388(4) Uani 1 1 d . . . H14A H 0.2619 -0.0118 0.6974 0.047 Uiso 1 1 calc R . . H14B H 0.1103 -0.0661 0.7324 0.047 Uiso 1 1 calc R . . C15 C 0.1961(2) 0.13080(19) 0.77126(8) 0.0343(4) Uani 1 1 d . . . H15A H 0.0986 0.1739 0.7855 0.041 Uiso 1 1 calc R . . H15B H 0.2374 0.0724 0.8077 0.041 Uiso 1 1 calc R . . C16 C 0.3111(2) 0.3661(2) 0.81442(7) 0.0353(4) Uani 1 1 d . . . H16A H 0.3777 0.4505 0.8042 0.053 Uiso 1 1 calc R . . H16B H 0.3504 0.3128 0.8520 0.053 Uiso 1 1 calc R . . H16C H 0.2093 0.4035 0.8238 0.053 Uiso 1 1 calc R . . C17 C 0.2254(2) 0.6182(3) 0.49814(8) 0.0468(5) Uani 1 1 d . . . H17A H 0.2786 0.6165 0.4568 0.070 Uiso 1 1 calc R . . H17B H 0.2282 0.7197 0.5159 0.070 Uiso 1 1 calc R . . H17C H 0.1200 0.5876 0.4917 0.070 Uiso 1 1 calc R . . C18 C 0.1908(2) 0.64521(18) 0.64292(8) 0.0314(3) Uani 1 1 d . . . H18A H 0.2862 0.7008 0.6449 0.047 Uiso 1 1 calc R . . H18B H 0.1528 0.6287 0.6866 0.047 Uiso 1 1 calc R . . H18C H 0.1165 0.7029 0.6183 0.047 Uiso 1 1 calc R . . C19 C 0.2757(2) 0.0809(2) 0.57374(8) 0.0345(4) Uani 1 1 d . . . H19A H 0.3497 0.1614 0.5796 0.052 Uiso 1 1 calc R . . H19B H 0.2674 0.0566 0.5280 0.052 Uiso 1 1 calc R . . H19C H 0.3087 -0.0080 0.5975 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0229(6) 0.0673(9) 0.0352(6) 0.0051(6) 0.0047(5) -0.0017(7) O2 0.0226(5) 0.0290(5) 0.0220(5) 0.0040(4) 0.0018(4) 0.0017(5) O3 0.0449(7) 0.0358(6) 0.0424(7) -0.0027(6) -0.0050(6) -0.0175(6) C1 0.0290(7) 0.0281(7) 0.0208(6) 0.0043(6) -0.0005(6) 0.0009(7) C2 0.0302(8) 0.0311(7) 0.0286(7) 0.0058(6) -0.0042(6) 0.0061(7) C3 0.0232(7) 0.0325(8) 0.0280(7) 0.0005(6) -0.0026(6) 0.0050(7) C4 0.0217(7) 0.0247(7) 0.0212(6) -0.0014(5) -0.0007(5) -0.0004(6) C5 0.0254(7) 0.0324(8) 0.0225(7) -0.0036(6) 0.0014(6) -0.0043(7) C6 0.0342(8) 0.0315(8) 0.0253(7) 0.0042(6) 0.0060(7) -0.0035(7) C7 0.0312(8) 0.0304(7) 0.0222(7) 0.0022(6) -0.0002(6) 0.0035(7) C8 0.0232(7) 0.0239(6) 0.0238(7) 0.0007(6) -0.0011(6) 0.0031(6) C9 0.0242(7) 0.0188(6) 0.0193(6) -0.0024(5) 0.0005(5) -0.0005(6) C10 0.0223(7) 0.0338(8) 0.0330(8) 0.0023(7) -0.0048(6) 0.0045(7) C11 0.0278(8) 0.0369(8) 0.0319(8) -0.0003(7) -0.0080(7) -0.0033(7) C12 0.0299(7) 0.0296(8) 0.0312(7) -0.0026(6) -0.0048(7) -0.0074(7) C13 0.0347(8) 0.0314(8) 0.0357(8) -0.0011(7) -0.0006(7) -0.0096(7) C14 0.0488(11) 0.0297(8) 0.0377(9) 0.0074(7) -0.0031(8) -0.0093(8) C15 0.0384(9) 0.0359(8) 0.0284(7) 0.0075(7) 0.0034(7) -0.0060(8) C16 0.0419(9) 0.0384(9) 0.0256(7) -0.0023(7) 0.0011(7) 0.0007(9) C17 0.0493(11) 0.0586(12) 0.0327(8) 0.0170(9) -0.0004(8) 0.0127(10) C18 0.0338(8) 0.0262(7) 0.0341(8) -0.0017(6) 0.0016(7) 0.0079(7) C19 0.0370(9) 0.0316(8) 0.0349(8) -0.0047(7) -0.0022(7) 0.0000(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 C5 1.225(2) . ? O2 C9 1.3400(17) . ? O2 C1 1.4798(17) . ? O3 C13 1.450(2) . ? O3 C12 1.469(2) . ? C1 C2 1.503(2) . ? C1 C16 1.524(2) . ? C1 C15 1.527(2) . ? C2 C3 1.327(2) . ? C2 H2A 0.9500 . ? C3 C4 1.460(2) . ? C3 H3A 0.9500 . ? C4 C9 1.361(2) . ? C4 C5 1.458(2) . ? C5 C6 1.504(2) . ? C6 C7 1.529(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C17 1.529(2) . ? C7 C8 1.550(2) . ? C7 H7A 1.0000 . ? C8 C9 1.514(2) . ? C8 C10 1.549(2) . ? C8 C18 1.555(2) . ? C10 C11 1.542(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.527(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.464(2) . ? C12 C19 1.507(3) . ? C13 C14 1.510(2) . ? C13 H13A 1.0000 . ? C14 C15 1.532(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C9 O2 C1 122.67(11) . . ? C13 O3 C12 60.18(10) . . ? O2 C1 C2 111.08(12) . . ? O2 C1 C16 106.87(12) . . ? C2 C1 C16 109.90(13) . . ? O2 C1 C15 105.11(12) . . ? C2 C1 C15 113.44(13) . . ? C16 C1 C15 110.15(13) . . ? C3 C2 C1 121.92(14) . . ? C3 C2 H2A 119.0 . . ? C1 C2 H2A 119.0 . . ? C2 C3 C4 120.57(14) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C9 C4 C5 120.76(14) . . ? C9 C4 C3 118.32(14) . . ? C5 C4 C3 120.75(14) . . ? O1 C5 C4 121.39(15) . . ? O1 C5 C6 121.67(15) . . ? C4 C5 C6 116.92(14) . . ? C5 C6 C7 113.05(13) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C17 C7 C6 110.10(15) . . ? C17 C7 C8 113.87(13) . . ? C6 C7 C8 111.71(12) . . ? C17 C7 H7A 106.9 . . ? C6 C7 H7A 106.9 . . ? C8 C7 H7A 106.9 . . ? C9 C8 C10 111.08(12) . . ? C9 C8 C7 109.09(12) . . ? C10 C8 C7 111.35(12) . . ? C9 C8 C18 106.17(11) . . ? C10 C8 C18 107.40(13) . . ? C7 C8 C18 111.65(12) . . ? O2 C9 C4 122.25(13) . . ? O2 C9 C8 112.01(12) . . ? C4 C9 C8 125.74(13) . . ? C11 C10 C8 119.57(14) . . ? C11 C10 H10A 107.4 . . ? C8 C10 H10A 107.4 . . ? C11 C10 H10B 107.4 . . ? C8 C10 H10B 107.4 . . ? H10A C10 H10B 107.0 . . ? C12 C11 C10 116.89(13) . . ? C12 C11 H11A 108.1 . . ? C10 C11 H11A 108.1 . . ? C12 C11 H11B 108.1 . . ? C10 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C13 C12 O3 59.26(10) . . ? C13 C12 C19 122.25(16) . . ? O3 C12 C19 111.67(14) . . ? C13 C12 C11 117.22(15) . . ? O3 C12 C11 114.75(14) . . ? C19 C12 C11 117.07(14) . . ? O3 C13 C12 60.56(10) . . ? O3 C13 C14 118.64(15) . . ? C12 C13 C14 125.83(17) . . ? O3 C13 H13A 113.8 . . ? C12 C13 H13A 113.8 . . ? C14 C13 H13A 113.8 . . ? C13 C14 C15 111.88(15) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C1 C15 C14 116.46(13) . . ? C1 C15 H15A 108.2 . . ? C14 C15 H15A 108.2 . . ? C1 C15 H15B 108.2 . . ? C14 C15 H15B 108.2 . . ? H15A C15 H15B 107.3 . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 C17 H17A 109.5 . . ? C7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C12 C19 H19A 109.5 . . ? C12 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C12 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C9 O2 C1 C2 -17.77(18) . . . . ? C9 O2 C1 C16 102.10(15) . . . . ? C9 O2 C1 C15 -140.85(13) . . . . ? O2 C1 C2 C3 18.5(2) . . . . ? C16 C1 C2 C3 -99.55(18) . . . . ? C15 C1 C2 C3 136.65(16) . . . . ? C1 C2 C3 C4 -7.1(2) . . . . ? C2 C3 C4 C9 -7.2(2) . . . . ? C2 C3 C4 C5 177.55(15) . . . . ? C9 C4 C5 O1 -178.54(16) . . . . ? C3 C4 C5 O1 -3.4(2) . . . . ? C9 C4 C5 C6 2.9(2) . . . . ? C3 C4 C5 C6 178.06(14) . . . . ? O1 C5 C6 C7 148.90(16) . . . . ? C4 C5 C6 C7 -32.55(19) . . . . ? C5 C6 C7 C17 -177.35(14) . . . . ? C5 C6 C7 C8 55.10(17) . . . . ? C17 C7 C8 C9 -171.71(14) . . . . ? C6 C7 C8 C9 -46.21(16) . . . . ? C17 C7 C8 C10 65.35(18) . . . . ? C6 C7 C8 C10 -169.15(13) . . . . ? C17 C7 C8 C18 -54.68(19) . . . . ? C6 C7 C8 C18 70.81(16) . . . . ? C1 O2 C9 C4 5.3(2) . . . . ? C1 O2 C9 C8 -175.34(12) . . . . ? C5 C4 C9 O2 -176.52(13) . . . . ? C3 C4 C9 O2 8.2(2) . . . . ? C5 C4 C9 C8 4.2(2) . . . . ? C3 C4 C9 C8 -171.09(13) . . . . ? C10 C8 C9 O2 -38.11(16) . . . . ? C7 C8 C9 O2 -161.21(12) . . . . ? C18 C8 C9 O2 78.34(14) . . . . ? C10 C8 C9 C4 141.26(15) . . . . ? C7 C8 C9 C4 18.16(19) . . . . ? C18 C8 C9 C4 -102.30(16) . . . . ? C9 C8 C10 C11 -66.81(17) . . . . ? C7 C8 C10 C11 54.99(18) . . . . ? C18 C8 C10 C11 177.51(13) . . . . ? C8 C10 C11 C12 65.4(2) . . . . ? C13 O3 C12 C19 115.58(16) . . . . ? C13 O3 C12 C11 -108.17(17) . . . . ? C10 C11 C12 C13 57.6(2) . . . . ? C10 C11 C12 O3 124.29(15) . . . . ? C10 C11 C12 C19 -101.90(17) . . . . ? C12 O3 C13 C14 -117.23(19) . . . . ? C19 C12 C13 O3 -97.64(16) . . . . ? C11 C12 C13 O3 104.00(15) . . . . ? O3 C12 C13 C14 105.74(18) . . . . ? C19 C12 C13 C14 8.1(3) . . . . ? C11 C12 C13 C14 -150.26(16) . . . . ? O3 C13 C14 C15 -175.36(14) . . . . ? C12 C13 C14 C15 111.89(19) . . . . ? O2 C1 C15 C14 59.11(18) . . . . ? C2 C1 C15 C14 -62.44(19) . . . . ? C16 C1 C15 C14 173.90(15) . . . . ? C13 C14 C15 C1 -70.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.207 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.031 data_04119 _database_code_depnum_ccdc_archive 'CCDC 280699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 04119 _chemical_melting_point ? _chemical_formula_moiety 'C19 H26 O4' _chemical_formula_sum 'C19 H26 O4' _chemical_formula_weight 318.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.826(1) _cell_length_b 10.4515(9) _cell_length_c 11.916(1) _cell_angle_alpha 90.00 _cell_angle_beta 106.751(2) _cell_angle_gamma 90.00 _cell_volume 1648.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3321 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925624 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18910 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3784 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0473P)^2^+0.2444P] 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_number_reflns 3784 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.29978(8) 0.98467(11) 0.96303(9) 0.0405(3) Uani 1 1 d . . . O2 O 0.11765(7) 0.80373(8) 0.61112(8) 0.0233(2) Uani 1 1 d . . . O3 O 0.01126(7) 0.93504(9) 0.67922(9) 0.0288(3) Uani 1 1 d . . . O4 O -0.02201(7) 0.82738(9) 0.74297(9) 0.0316(3) Uani 1 1 d . . . C1 C 0.26644(11) 0.97764(14) 0.85676(12) 0.0272(3) Uani 1 1 d . . . C2 C 0.17772(10) 0.89543(13) 0.80347(12) 0.0225(3) Uani 1 1 d . . . C3 C 0.14743(11) 0.79633(14) 0.85451(13) 0.0264(3) Uani 1 1 d . . . H3A H 0.1779(12) 0.7697(14) 0.9348(14) 0.032(4) Uiso 1 1 d . . . C4 C 0.05847(11) 0.73237(14) 0.77244(13) 0.0271(3) Uani 1 1 d . . . H4A H 0.0308(12) 0.6632(16) 0.8055(13) 0.032(4) Uiso 1 1 d . . . C5 C 0.08005(11) 0.69031(13) 0.65756(12) 0.0246(3) Uani 1 1 d . . . C6 C 0.11428(10) 0.91435(13) 0.67850(12) 0.0222(3) Uani 1 1 d . . . C7 C 0.14509(11) 1.02851(14) 0.61998(14) 0.0270(3) Uani 1 1 d . . . H7A H 0.1229(11) 1.1052(15) 0.6524(13) 0.027(4) Uiso 1 1 d . . . H7B H 0.1103(11) 1.0244(14) 0.5350(14) 0.030(4) Uiso 1 1 d . . . C8 C 0.26036(11) 1.02775(14) 0.64443(13) 0.0275(3) Uani 1 1 d . . . H8A H 0.2787(10) 0.9393(14) 0.6255(12) 0.023(4) Uiso 1 1 d . . . C9 C 0.31559(11) 1.05162(14) 0.77624(13) 0.0285(3) Uani 1 1 d . . . C10 C 0.42839(12) 1.01179(17) 0.80862(16) 0.0363(4) Uani 1 1 d . . . H10A H 0.4665(13) 1.0766(17) 0.7749(15) 0.045(5) Uiso 1 1 d . . . H10B H 0.4583(12) 1.0199(15) 0.8957(15) 0.040(5) Uiso 1 1 d . . . C11 C 0.45243(12) 0.87749(17) 0.77021(16) 0.0389(4) Uani 1 1 d . . . H11A H 0.4387(12) 0.8759(15) 0.6832(15) 0.035(4) Uiso 1 1 d . . . H11B H 0.5259(14) 0.8659(16) 0.8012(15) 0.047(5) Uiso 1 1 d . . . C12 C 0.39834(11) 0.76813(15) 0.80855(14) 0.0330(4) Uani 1 1 d . . . C13 C 0.32752(11) 0.70096(15) 0.73182(14) 0.0295(3) Uani 1 1 d . . . H13A H 0.3137(11) 0.7221(14) 0.6508(14) 0.028(4) Uiso 1 1 d . . . C14 C 0.26361(12) 0.59620(15) 0.75877(14) 0.0324(4) Uani 1 1 d . . . H14A H 0.2580(13) 0.6051(16) 0.8410(16) 0.049(5) Uiso 1 1 d . . . H14B H 0.2974(12) 0.5151(17) 0.7550(14) 0.041(5) Uiso 1 1 d . . . C15 C 0.15769(12) 0.58205(14) 0.67217(14) 0.0282(3) Uani 1 1 d . . . H15A H 0.1654(11) 0.5658(14) 0.5931(14) 0.031(4) Uiso 1 1 d . . . H15B H 0.1262(11) 0.5037(15) 0.6953(13) 0.029(4) Uiso 1 1 d . . . C16 C -0.01829(13) 0.65127(17) 0.56733(15) 0.0324(4) Uani 1 1 d . . . H16A H -0.0044(12) 0.6303(15) 0.4913(15) 0.040(4) Uiso 1 1 d . . . H16B H -0.0673(13) 0.7210(17) 0.5549(14) 0.042(5) Uiso 1 1 d . . . H16C H -0.0469(12) 0.5736(16) 0.5958(14) 0.038(4) Uiso 1 1 d . . . C17 C 0.42895(13) 0.73879(18) 0.93868(14) 0.0459(5) Uani 1 1 d . . . H17A H 0.3844 0.6725 0.9544 0.069 Uiso 0.50 1 calc PR . . H17B H 0.4232 0.8165 0.9823 0.069 Uiso 0.50 1 calc PR . . H17C H 0.4990 0.7084 0.9634 0.069 Uiso 0.50 1 calc PR . . H17D H 0.4866 0.7924 0.9790 0.069 Uiso 0.50 1 calc PR . . H17E H 0.4479 0.6484 0.9511 0.069 Uiso 0.50 1 calc PR . . H17F H 0.3721 0.7566 0.9700 0.069 Uiso 0.50 1 calc PR . . C18 C 0.31060(15) 1.19399(16) 0.80938(17) 0.0393(4) Uani 1 1 d . . . H18A H 0.3426(13) 1.2023(16) 0.8932(16) 0.047(5) Uiso 1 1 d . . . H18B H 0.2378(15) 1.2297(17) 0.7868(15) 0.050(5) Uiso 1 1 d . . . H18C H 0.3495(14) 1.2483(18) 0.7699(16) 0.055(5) Uiso 1 1 d . . . C19 C 0.29221(16) 1.11995(19) 0.56236(17) 0.0436(4) Uani 1 1 d . . . H19A H 0.2581(13) 1.0935(17) 0.4821(17) 0.047(5) Uiso 1 1 d . . . H19B H 0.3658(16) 1.1212(17) 0.5791(16) 0.054(5) Uiso 1 1 d . . . H19C H 0.2689(14) 1.2094(19) 0.5694(16) 0.054(6) Uiso 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 0.0398(7) 0.0559(8) 0.0250(6) -0.0096(5) 0.0079(5) -0.0087(6) O2 0.0302(5) 0.0184(5) 0.0235(5) -0.0022(4) 0.0110(4) -0.0034(4) O3 0.0252(5) 0.0239(5) 0.0386(6) 0.0021(4) 0.0114(5) 0.0016(4) O4 0.0292(6) 0.0263(6) 0.0458(6) -0.0016(5) 0.0207(5) -0.0030(4) C1 0.0268(8) 0.0296(8) 0.0257(8) -0.0057(6) 0.0085(6) 0.0016(6) C2 0.0247(7) 0.0229(7) 0.0225(7) -0.0036(6) 0.0106(6) 0.0011(6) C3 0.0326(8) 0.0273(8) 0.0229(7) -0.0010(6) 0.0139(6) 0.0031(6) C4 0.0326(8) 0.0209(8) 0.0334(8) -0.0002(6) 0.0188(7) -0.0020(6) C5 0.0301(8) 0.0190(7) 0.0273(7) -0.0007(6) 0.0125(6) -0.0048(6) C6 0.0217(7) 0.0204(7) 0.0250(7) -0.0028(6) 0.0074(6) -0.0007(6) C7 0.0325(8) 0.0207(8) 0.0278(8) 0.0012(6) 0.0085(7) -0.0016(6) C8 0.0326(8) 0.0245(8) 0.0283(8) -0.0011(6) 0.0135(6) -0.0052(7) C9 0.0292(8) 0.0282(8) 0.0297(8) -0.0074(6) 0.0114(7) -0.0083(6) C10 0.0272(8) 0.0427(10) 0.0398(10) -0.0104(8) 0.0112(7) -0.0094(7) C11 0.0223(9) 0.0522(11) 0.0431(10) -0.0129(8) 0.0106(8) -0.0015(8) C12 0.0257(8) 0.0387(9) 0.0345(8) -0.0062(7) 0.0086(7) 0.0082(7) C13 0.0293(8) 0.0316(8) 0.0291(8) -0.0019(7) 0.0110(7) 0.0084(7) C14 0.0378(9) 0.0259(8) 0.0344(9) 0.0019(7) 0.0117(7) 0.0075(7) C15 0.0361(9) 0.0212(8) 0.0307(8) -0.0022(6) 0.0151(7) -0.0015(7) C16 0.0328(9) 0.0271(9) 0.0376(9) -0.0077(7) 0.0103(7) -0.0067(7) C17 0.0369(9) 0.0558(12) 0.0377(10) -0.0039(8) -0.0010(8) 0.0099(9) C18 0.0432(11) 0.0301(9) 0.0467(11) -0.0138(8) 0.0162(9) -0.0124(8) C19 0.0522(12) 0.0421(11) 0.0422(11) 0.0030(9) 0.0226(9) -0.0147(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 C1 1.2185(17) . ? O2 C6 1.4160(16) . ? O2 C5 1.4656(16) . ? O3 C6 1.4431(16) . ? O3 O4 1.5020(14) . ? O4 C4 1.4568(18) . ? C1 C2 1.482(2) . ? C1 C9 1.535(2) . ? C2 C3 1.328(2) . ? C2 C6 1.5077(19) . ? C3 C4 1.491(2) . ? C3 H3A 0.969(16) . ? C4 C5 1.547(2) . ? C4 H4A 0.954(16) . ? C5 C16 1.526(2) . ? C5 C15 1.535(2) . ? C6 C7 1.504(2) . ? C7 C8 1.535(2) . ? C7 H7A 0.976(15) . ? C7 H7B 0.989(16) . ? C8 C19 1.526(2) . ? C8 C9 1.556(2) . ? C8 H8A 1.001(15) . ? C9 C18 1.546(2) . ? C9 C10 1.552(2) . ? C10 C11 1.542(2) . ? C10 H10A 1.010(18) . ? C10 H10B 1.004(17) . ? C11 C12 1.507(2) . ? C11 H11A 0.999(16) . ? C11 H11B 0.983(18) . ? C12 C13 1.331(2) . ? C12 C17 1.516(2) . ? C13 C14 1.499(2) . ? C13 H13A 0.955(15) . ? C14 C15 1.536(2) . ? C14 H14A 1.009(18) . ? C14 H14B 0.975(17) . ? C15 H15A 0.994(16) . ? C15 H15B 1.003(16) . ? C16 H16A 1.003(17) . ? C16 H16B 0.977(18) . ? C16 H16C 1.004(17) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C18 H18A 0.973(18) . ? C18 H18B 1.034(19) . ? C18 H18C 0.99(2) . ? C19 H19A 0.976(19) . ? C19 H19B 0.98(2) . ? C19 H19C 1.000(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 C6 O2 C5 111.90(10) . . ? C6 O3 O4 109.72(9) . . ? C4 O4 O3 107.97(9) . . ? O1 C1 C2 119.91(13) . . ? O1 C1 C9 121.08(13) . . ? C2 C1 C9 119.01(12) . . ? C3 C2 C1 125.94(13) . . ? C3 C2 C6 112.58(12) . . ? C1 C2 C6 121.41(12) . . ? C2 C3 C4 111.01(13) . . ? C2 C3 H3A 124.8(9) . . ? C4 C3 H3A 124.1(9) . . ? O4 C4 C3 106.31(11) . . ? O4 C4 C5 108.01(12) . . ? C3 C4 C5 112.02(12) . . ? O4 C4 H4A 104.3(9) . . ? C3 C4 H4A 114.9(9) . . ? C5 C4 H4A 110.7(9) . . ? O2 C5 C16 106.93(12) . . ? O2 C5 C15 109.06(11) . . ? C16 C5 C15 109.57(12) . . ? O2 C5 C4 106.51(11) . . ? C16 C5 C4 109.86(12) . . ? C15 C5 C4 114.60(12) . . ? O2 C6 O3 108.64(10) . . ? O2 C6 C7 108.95(11) . . ? O3 C6 C7 107.20(11) . . ? O2 C6 C2 110.37(11) . . ? O3 C6 C2 107.94(11) . . ? C7 C6 C2 113.58(12) . . ? C6 C7 C8 108.97(12) . . ? C6 C7 H7A 107.7(8) . . ? C8 C7 H7A 110.9(9) . . ? C6 C7 H7B 108.7(9) . . ? C8 C7 H7B 111.4(9) . . ? H7A C7 H7B 109.0(12) . . ? C19 C8 C7 110.53(14) . . ? C19 C8 C9 113.42(13) . . ? C7 C8 C9 111.80(12) . . ? C19 C8 H8A 107.5(8) . . ? C7 C8 H8A 106.1(8) . . ? C9 C8 H8A 107.0(8) . . ? C1 C9 C18 105.35(12) . . ? C1 C9 C10 107.68(13) . . ? C18 C9 C10 108.08(13) . . ? C1 C9 C8 111.92(11) . . ? C18 C9 C8 111.54(13) . . ? C10 C9 C8 111.94(12) . . ? C11 C10 C9 117.23(13) . . ? C11 C10 H10A 108.1(10) . . ? C9 C10 H10A 108.9(10) . . ? C11 C10 H10B 108.9(9) . . ? C9 C10 H10B 108.6(9) . . ? H10A C10 H10B 104.4(13) . . ? C12 C11 C10 115.60(13) . . ? C12 C11 H11A 109.9(9) . . ? C10 C11 H11A 109.3(9) . . ? C12 C11 H11B 110.0(10) . . ? C10 C11 H11B 106.8(10) . . ? H11A C11 H11B 104.7(14) . . ? C13 C12 C11 121.52(15) . . ? C13 C12 C17 121.95(16) . . ? C11 C12 C17 116.53(14) . . ? C12 C13 C14 126.91(15) . . ? C12 C13 H13A 117.8(9) . . ? C14 C13 H13A 115.3(9) . . ? C13 C14 C15 115.67(13) . . ? C13 C14 H14A 110.9(10) . . ? C15 C14 H14A 109.6(10) . . ? C13 C14 H14B 107.8(10) . . ? C15 C14 H14B 105.2(10) . . ? H14A C14 H14B 107.2(14) . . ? C5 C15 C14 120.36(12) . . ? C5 C15 H15A 106.4(9) . . ? C14 C15 H15A 108.1(9) . . ? C5 C15 H15B 106.8(9) . . ? C14 C15 H15B 107.4(9) . . ? H15A C15 H15B 107.2(12) . . ? C5 C16 H16A 109.3(10) . . ? C5 C16 H16B 110.2(10) . . ? H16A C16 H16B 109.3(13) . . ? C5 C16 H16C 109.6(9) . . ? H16A C16 H16C 109.0(13) . . ? H16B C16 H16C 109.3(13) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C12 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C12 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C9 C18 H18A 107.9(10) . . ? C9 C18 H18B 113.1(10) . . ? H18A C18 H18B 110.8(14) . . ? C9 C18 H18C 111.1(11) . . ? H18A C18 H18C 106.8(15) . . ? H18B C18 H18C 106.9(14) . . ? C8 C19 H19A 107.6(10) . . ? C8 C19 H19B 110.6(11) . . ? H19A C19 H19B 112.6(15) . . ? C8 C19 H19C 112.1(11) . . ? H19A C19 H19C 105.7(15) . . ? H19B C19 H19C 108.1(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 C6 O3 O4 C4 -5.43(13) . . . . ? O1 C1 C2 C3 -22.9(2) . . . . ? C9 C1 C2 C3 156.44(14) . . . . ? O1 C1 C2 C6 160.37(13) . . . . ? C9 C1 C2 C6 -20.33(19) . . . . ? C1 C2 C3 C4 -177.15(12) . . . . ? C6 C2 C3 C4 -0.13(16) . . . . ? O3 O4 C4 C3 63.61(13) . . . . ? O3 O4 C4 C5 -56.79(13) . . . . ? C2 C3 C4 O4 -61.84(15) . . . . ? C2 C3 C4 C5 55.93(16) . . . . ? C6 O2 C5 C16 112.59(12) . . . . ? C6 O2 C5 C15 -129.02(12) . . . . ? C6 O2 C5 C4 -4.84(15) . . . . ? O4 C4 C5 O2 63.92(14) . . . . ? C3 C4 C5 O2 -52.83(15) . . . . ? O4 C4 C5 C16 -51.55(15) . . . . ? C3 C4 C5 C16 -168.30(13) . . . . ? O4 C4 C5 C15 -175.40(11) . . . . ? C3 C4 C5 C15 67.85(16) . . . . ? C5 O2 C6 O3 -58.57(13) . . . . ? C5 O2 C6 C7 -175.05(11) . . . . ? C5 O2 C6 C2 59.59(14) . . . . ? O4 O3 C6 O2 65.66(12) . . . . ? O4 O3 C6 C7 -176.75(10) . . . . ? O4 O3 C6 C2 -54.04(12) . . . . ? C3 C2 C6 O2 -59.11(15) . . . . ? C1 C2 C6 O2 118.06(13) . . . . ? C3 C2 C6 O3 59.48(14) . . . . ? C1 C2 C6 O3 -123.35(13) . . . . ? C3 C2 C6 C7 178.20(12) . . . . ? C1 C2 C6 C7 -4.63(18) . . . . ? O2 C6 C7 C8 -76.80(14) . . . . ? O3 C6 C7 C8 165.81(11) . . . . ? C2 C6 C7 C8 46.67(16) . . . . ? C6 C7 C8 C19 165.37(13) . . . . ? C6 C7 C8 C9 -67.27(16) . . . . ? O1 C1 C9 C18 -58.73(19) . . . . ? C2 C1 C9 C18 121.98(14) . . . . ? O1 C1 C9 C10 56.44(18) . . . . ? C2 C1 C9 C10 -122.86(14) . . . . ? O1 C1 C9 C8 179.88(14) . . . . ? C2 C1 C9 C8 0.59(19) . . . . ? C19 C8 C9 C1 167.83(14) . . . . ? C7 C8 C9 C1 42.04(17) . . . . ? C19 C8 C9 C18 50.08(18) . . . . ? C7 C8 C9 C18 -75.71(16) . . . . ? C19 C8 C9 C10 -71.17(18) . . . . ? C7 C8 C9 C10 163.04(13) . . . . ? C1 C9 C10 C11 73.56(17) . . . . ? C18 C9 C10 C11 -173.10(15) . . . . ? C8 C9 C10 C11 -49.87(19) . . . . ? C9 C10 C11 C12 -54.1(2) . . . . ? C10 C11 C12 C13 111.30(17) . . . . ? C10 C11 C12 C17 -68.78(19) . . . . ? C11 C12 C13 C14 -175.73(14) . . . . ? C17 C12 C13 C14 4.3(2) . . . . ? C12 C13 C14 C15 149.69(15) . . . . ? O2 C5 C15 C14 63.61(17) . . . . ? C16 C5 C15 C14 -179.66(14) . . . . ? C4 C5 C15 C14 -55.66(18) . . . . ? C13 C14 C15 C5 -63.62(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.252 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.040