data_exp_1614 _audit_creation_date 2013-10-14 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H26 O4' _chemical_formula_sum 'C20 H26 O4' _chemical_formula_weight 330.41 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'orthorhombic' _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 7.3028(3) _cell_length_b 13.9746(13) _cell_length_c 16.4665(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1680.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3328 _cell_measurement_temperature 99.8 _cell_measurement_theta_max 71.6183 _cell_measurement_theta_min 4.1425 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5578 _diffrn_reflns_theta_full 71.96 _diffrn_reflns_theta_max 71.96 _diffrn_reflns_theta_min 4.15 _diffrn_ambient_temperature 99.8 _diffrn_detector_area_resol_mean 16.0971 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -7.00 44.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 0.0000 42.0000 -83.0000 51 #__ type_ start__ end____ width___ exp.time_ 2 omega -92.00 -46.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - -42.5000 125.0000 -150.0000 46 #__ type_ start__ end____ width___ exp.time_ 3 omega -49.00 30.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 -90.0000 79 #__ type_ start__ end____ width___ exp.time_ 4 omega -5.00 50.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 56.0000 -37.0000 120.0000 55 #__ type_ start__ end____ width___ exp.time_ 5 omega -6.00 68.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 56.0000 -37.0000 -120.0000 74 #__ type_ start__ end____ width___ exp.time_ 6 omega 150.00 175.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 55.00 162.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -15.0000 60.0000 107 #__ type_ start__ end____ width___ exp.time_ 8 omega 111.00 167.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 90.0000 56 #__ type_ start__ end____ width___ exp.time_ 9 omega 101.00 127.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 150.00 176.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 85.00 120.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 12 omega 106.00 173.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 -180.0000 67 #__ type_ start__ end____ width___ exp.time_ 13 omega 119.00 174.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 111.0000 120.0000 55 #__ type_ start__ end____ width___ exp.time_ 14 omega 89.00 136.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 -180.0000 47 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1035056000 _diffrn_orient_matrix_UB_12 0.0378793000 _diffrn_orient_matrix_UB_13 -0.0747211000 _diffrn_orient_matrix_UB_21 -0.0377841000 _diffrn_orient_matrix_UB_22 0.1034759000 _diffrn_orient_matrix_UB_23 0.0274541000 _diffrn_orient_matrix_UB_31 0.1794903000 _diffrn_orient_matrix_UB_32 -0.0002097000 _diffrn_orient_matrix_UB_33 0.0490286000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3157 _reflns_number_total 3215 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.271 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(16) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0344 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.3433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0882 _refine_ls_wR_factor_ref 0.0888 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C2 C -0.0008(2) 0.31098(10) 0.11768(8) 0.0134(3) Uani 1 1 d . . . C6 C -0.17057(19) 0.18618(9) 0.20747(8) 0.0120(3) Uani 1 1 d . . . C12 C -0.35781(18) 0.24581(10) 0.33175(8) 0.0127(3) Uani 1 1 d . . . H12 H -0.2647 0.2278 0.3718 0.015 Uiso 1 1 calc R . . O2 O 0.24219(14) 0.23608(8) 0.08395(6) 0.0199(2) Uani 1 1 d . . . C13 C -0.32109(19) 0.35016(9) 0.30589(8) 0.0127(3) Uani 1 1 d . . . H13A H -0.4276 0.3748 0.2776 0.015 Uiso 1 1 calc R . . H13B H -0.3024 0.3890 0.3540 0.015 Uiso 1 1 calc R . . C9 C -0.5574(2) 0.06192(10) 0.33489(9) 0.0176(3) Uani 1 1 d . . . H9A H -0.6531 0.0687 0.2944 0.021 Uiso 1 1 calc R . . H9B H -0.5675 -0.0015 0.3585 0.021 Uiso 1 1 calc R . . C7 C -0.34607(19) 0.17447(10) 0.26039(8) 0.0125(3) Uani 1 1 d . . . H7 H -0.4511 0.1872 0.2250 0.015 Uiso 1 1 calc R . . C11 C -0.54876(19) 0.23840(10) 0.37335(8) 0.0146(3) Uani 1 1 d . . . H11 H -0.6408 0.2539 0.3321 0.018 Uiso 1 1 calc R . . O4 O -0.31862(13) 0.31541(7) 0.12944(6) 0.0130(2) Uani 1 1 d . . . H4 H -0.4107 0.3107 0.1577 0.019 Uiso 1 1 calc R . . C16 C -0.0209(2) 0.40741(10) 0.07329(9) 0.0163(3) Uani 1 1 d . . . H16A H -0.1321 0.4074 0.0423 0.025 Uiso 1 1 calc R . . H16B H 0.0815 0.4166 0.0376 0.025 Uiso 1 1 calc R . . H16C H -0.0245 0.4583 0.1124 0.025 Uiso 1 1 calc R . . C4 C -0.0253(2) 0.12816(11) 0.07354(9) 0.0192(3) Uani 1 1 d . . . H4A H 0.0740 0.0898 0.0952 0.023 Uiso 1 1 calc R . . H4B H -0.0612 0.1002 0.0220 0.023 Uiso 1 1 calc R . . O3 O -0.03061(15) 0.41248(7) 0.26524(6) 0.0182(2) Uani 1 1 d . . . C15 C -0.16043(18) 0.29233(9) 0.17700(8) 0.0107(3) Uani 1 1 d . . . C17 C 0.0005(2) 0.16063(10) 0.25705(9) 0.0152(3) Uani 1 1 d . . . H17A H 0.0103 0.2031 0.3027 0.023 Uiso 1 1 calc R . . H17B H 0.1073 0.1669 0.2235 0.023 Uiso 1 1 calc R . . H17C H -0.0091 0.0959 0.2760 0.023 Uiso 1 1 calc R . . C1 C 0.2007(2) 0.30120(10) 0.14204(8) 0.0153(3) Uani 1 1 d . . . C3 C 0.04627(19) 0.22873(11) 0.05784(9) 0.0168(3) Uani 1 1 d . . . H3 H 0.0296 0.2480 0.0011 0.020 Uiso 1 1 calc R . . C8 C -0.3704(2) 0.07252(10) 0.29406(9) 0.0170(3) Uani 1 1 d . . . H8A H -0.3599 0.0266 0.2501 0.020 Uiso 1 1 calc R . . H8B H -0.2745 0.0591 0.3332 0.020 Uiso 1 1 calc R . . C14 C -0.15575(19) 0.35879(9) 0.25143(8) 0.0116(3) Uani 1 1 d . . . C18 C -0.6299(2) 0.11228(12) 0.47524(10) 0.0226(3) Uani 1 1 d . . . H18A H -0.6471 0.0483 0.4889 0.027 Uiso 1 1 calc R . . H18B H -0.6452 0.1596 0.5143 0.027 Uiso 1 1 calc R . . C20 C -0.6979(2) 0.37653(11) 0.44221(11) 0.0266(4) Uani 1 1 d . . . H20A H -0.7816 0.3812 0.3998 0.032 Uiso 1 1 calc R . . H20B H -0.7042 0.4189 0.4857 0.032 Uiso 1 1 calc R . . C10 C -0.58371(19) 0.13587(10) 0.40016(9) 0.0162(3) Uani 1 1 d . . . C5 C -0.1881(2) 0.12179(10) 0.13203(9) 0.0166(3) Uani 1 1 d . . . H5A H -0.2013 0.0559 0.1497 0.020 Uiso 1 1 calc R . . H5B H -0.2987 0.1392 0.1029 0.020 Uiso 1 1 calc R . . C19 C -0.5699(2) 0.30967(11) 0.44062(9) 0.0183(3) Uani 1 1 d . . . H19 H -0.4881 0.3067 0.4838 0.022 Uiso 1 1 calc R . . O1 O 0.30921(14) 0.33678(7) 0.18722(6) 0.0175(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0131(7) 0.0158(6) 0.0112(6) -0.0006(5) -0.0007(5) -0.0015(6) C6 0.0114(6) 0.0109(6) 0.0136(6) -0.0007(5) 0.0000(5) -0.0005(5) C12 0.0130(6) 0.0139(6) 0.0113(6) 0.0017(5) -0.0007(5) -0.0006(5) O2 0.0122(5) 0.0261(5) 0.0215(5) -0.0060(4) 0.0024(4) 0.0024(4) C13 0.0151(6) 0.0120(6) 0.0108(6) -0.0019(5) -0.0004(5) 0.0003(5) C9 0.0167(7) 0.0134(7) 0.0227(7) 0.0036(6) -0.0006(6) -0.0024(5) C7 0.0109(6) 0.0123(6) 0.0143(6) -0.0004(5) -0.0012(5) 0.0005(5) C11 0.0133(6) 0.0174(7) 0.0131(6) 0.0015(6) 0.0002(5) 0.0000(6) O4 0.0092(5) 0.0183(5) 0.0113(4) 0.0006(4) -0.0006(4) 0.0011(4) C16 0.0134(7) 0.0202(7) 0.0154(6) 0.0041(6) 0.0015(5) -0.0004(6) C4 0.0183(7) 0.0199(7) 0.0194(7) -0.0076(6) 0.0019(6) 0.0022(6) O3 0.0180(5) 0.0189(5) 0.0178(5) -0.0028(4) 0.0010(4) -0.0045(4) C15 0.0080(6) 0.0127(6) 0.0115(6) 0.0000(5) -0.0004(5) 0.0005(5) C17 0.0123(6) 0.0150(6) 0.0183(7) 0.0019(5) -0.0008(5) 0.0017(5) C1 0.0134(7) 0.0177(7) 0.0148(6) 0.0035(5) 0.0019(6) -0.0001(5) C3 0.0124(7) 0.0233(7) 0.0145(6) -0.0032(6) 0.0015(5) 0.0016(5) C8 0.0171(7) 0.0127(7) 0.0211(7) 0.0019(6) 0.0022(6) 0.0010(5) C14 0.0138(6) 0.0091(6) 0.0120(6) 0.0014(5) -0.0027(5) 0.0014(5) C18 0.0212(7) 0.0224(8) 0.0242(8) 0.0067(6) 0.0037(6) -0.0001(6) C20 0.0299(8) 0.0202(7) 0.0296(8) -0.0040(6) 0.0109(7) -0.0024(6) C10 0.0089(6) 0.0188(7) 0.0209(7) 0.0039(6) -0.0009(5) -0.0007(5) C5 0.0163(7) 0.0146(6) 0.0188(6) -0.0049(6) 0.0007(6) 0.0002(6) C19 0.0186(7) 0.0218(7) 0.0145(6) -0.0002(6) 0.0052(6) -0.0063(6) O1 0.0112(5) 0.0229(5) 0.0184(5) 0.0010(4) -0.0023(4) -0.0012(4) _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 C2 C16 1.5401(19) . ? C2 C15 1.5432(19) . ? C2 C1 1.5309(19) . ? C2 C3 1.5524(19) . ? C6 C7 1.5585(18) . ? C6 C15 1.5677(17) . ? C6 C17 1.5346(19) . ? C6 C5 1.5393(18) . ? C12 H12 0.9800 . ? C12 C13 1.5426(18) . ? C12 C7 1.5434(18) . ? C12 C11 1.5571(18) . ? O2 C1 1.3548(18) . ? O2 C3 1.4975(17) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.5089(19) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C8 1.529(2) . ? C9 C10 1.503(2) . ? C7 H7 0.9800 . ? C7 C8 1.5390(19) . ? C11 H11 0.9800 . ? C11 C10 1.5209(19) . ? C11 C19 1.498(2) . ? O4 H4 0.8200 . ? O4 C15 1.4324(16) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C3 1.522(2) . ? C4 C5 1.532(2) . ? O3 C14 1.2041(18) . ? C15 C14 1.5382(18) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C1 O1 1.1953(18) . ? C3 H3 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C18 H18A 0.9300 . ? C18 H18B 0.9300 . ? C18 C10 1.323(2) . ? C20 H20A 0.9300 . ? C20 H20B 0.9300 . ? C20 C19 1.322(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C19 H19 0.9300 . ? 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 C16 C2 C15 112.09(11) . . ? C16 C2 C3 111.58(11) . . ? C15 C2 C3 116.35(11) . . ? C1 C2 C16 107.10(11) . . ? C1 C2 C15 123.03(11) . . ? C1 C2 C3 83.55(11) . . ? C7 C6 C15 108.50(11) . . ? C17 C6 C7 110.34(11) . . ? C17 C6 C15 110.61(11) . . ? C17 C6 C5 111.15(11) . . ? C5 C6 C7 108.76(11) . . ? C5 C6 C15 107.38(11) . . ? C13 C12 H12 107.9 . . ? C13 C12 C7 113.01(11) . . ? C13 C12 C11 109.88(11) . . ? C7 C12 H12 107.9 . . ? C7 C12 C11 109.98(11) . . ? C11 C12 H12 107.9 . . ? C1 O2 C3 92.01(10) . . ? C12 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C14 C13 C12 112.25(11) . . ? C14 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? H9A C9 H9B 108.0 . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C10 C9 C8 111.21(12) . . ? C6 C7 H7 107.0 . . ? C12 C7 C6 113.80(11) . . ? C12 C7 H7 107.0 . . ? C8 C7 C6 113.19(11) . . ? C8 C7 C12 108.50(11) . . ? C8 C7 H7 107.0 . . ? C12 C11 H11 107.1 . . ? C10 C11 C12 109.92(11) . . ? C10 C11 H11 107.1 . . ? C19 C11 C12 111.92(12) . . ? C19 C11 H11 107.1 . . ? C19 C11 C10 113.24(12) . . ? C15 O4 H4 109.5 . . ? C2 C16 H16A 109.5 . . ? C2 C16 H16B 109.5 . . ? C2 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? H4A C4 H4B 107.5 . . ? C3 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? C3 C4 C5 115.27(12) . . ? C5 C4 H4A 108.5 . . ? C5 C4 H4B 108.5 . . ? C2 C15 C6 113.46(11) . . ? O4 C15 C2 103.02(10) . . ? O4 C15 C6 110.49(11) . . ? O4 C15 C14 108.51(10) . . ? C14 C15 C2 112.68(11) . . ? C14 C15 C6 108.50(10) . . ? C6 C17 H17A 109.5 . . ? C6 C17 H17B 109.5 . . ? C6 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C1 C2 95.16(11) . . ? O1 C1 C2 139.75(14) . . ? O1 C1 O2 124.78(13) . . ? C2 C3 H3 111.9 . . ? O2 C3 C2 88.76(10) . . ? O2 C3 C4 110.05(12) . . ? O2 C3 H3 111.9 . . ? C4 C3 C2 120.00(12) . . ? C4 C3 H3 111.9 . . ? C9 C8 C7 110.56(12) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C13 C14 C15 114.06(11) . . ? O3 C14 C13 123.02(12) . . ? O3 C14 C15 122.93(12) . . ? H18A C18 H18B 120.0 . . ? C10 C18 H18A 120.0 . . ? C10 C18 H18B 120.0 . . ? H20A C20 H20B 120.0 . . ? C19 C20 H20A 120.0 . . ? C19 C20 H20B 120.0 . . ? C9 C10 C11 114.74(12) . . ? C18 C10 C9 121.96(14) . . ? C18 C10 C11 123.28(14) . . ? C6 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 C6 114.14(12) . . ? C4 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C11 C19 H19 118.1 . . ? C20 C19 C11 123.89(14) . . ? C20 C19 H19 118.1 . . ? 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 C15 C14 C13 173.50(11) . . . . ? C2 C15 C14 O3 -6.95(18) . . . . ? C6 C7 C8 C9 -171.88(12) . . . . ? C6 C15 C14 C13 -60.00(14) . . . . ? C6 C15 C14 O3 119.55(14) . . . . ? C12 C13 C14 O3 -126.59(14) . . . . ? C12 C13 C14 C15 52.96(14) . . . . ? C12 C7 C8 C9 60.80(15) . . . . ? C12 C11 C10 C9 -51.99(16) . . . . ? C12 C11 C10 C18 126.64(15) . . . . ? C12 C11 C19 C20 120.15(16) . . . . ? C13 C12 C7 C6 48.83(15) . . . . ? C13 C12 C7 C8 175.80(11) . . . . ? C13 C12 C11 C10 -179.03(11) . . . . ? C13 C12 C11 C19 -52.29(15) . . . . ? C7 C6 C15 C2 -175.05(11) . . . . ? C7 C6 C15 O4 -59.95(13) . . . . ? C7 C6 C15 C14 58.90(13) . . . . ? C7 C6 C5 C4 178.76(12) . . . . ? C7 C12 C13 C14 -45.85(15) . . . . ? C7 C12 C11 C10 55.95(14) . . . . ? C7 C12 C11 C19 -177.31(12) . . . . ? C11 C12 C13 C14 -169.10(11) . . . . ? C11 C12 C7 C6 172.03(11) . . . . ? C11 C12 C7 C8 -61.00(14) . . . . ? O4 C15 C14 C13 60.08(14) . . . . ? O4 C15 C14 O3 -120.37(14) . . . . ? C16 C2 C15 C6 166.25(11) . . . . ? C16 C2 C15 O4 46.79(13) . . . . ? C16 C2 C15 C14 -69.95(14) . . . . ? C16 C2 C1 O2 -105.08(11) . . . . ? C16 C2 C1 O1 68.2(2) . . . . ? C16 C2 C3 O2 100.86(12) . . . . ? C16 C2 C3 C4 -146.59(13) . . . . ? C15 C2 C1 O2 122.90(13) . . . . ? C15 C2 C1 O1 -63.9(2) . . . . ? C15 C2 C3 O2 -128.80(12) . . . . ? C15 C2 C3 C4 -16.25(19) . . . . ? C15 C6 C7 C12 -55.38(14) . . . . ? C15 C6 C7 C8 -179.87(11) . . . . ? C15 C6 C5 C4 61.54(15) . . . . ? C17 C6 C7 C12 65.94(14) . . . . ? C17 C6 C7 C8 -58.55(14) . . . . ? C17 C6 C15 C2 63.79(14) . . . . ? C17 C6 C15 O4 178.90(10) . . . . ? C17 C6 C15 C14 -62.26(14) . . . . ? C17 C6 C5 C4 -59.57(15) . . . . ? C1 C2 C15 C6 -63.77(16) . . . . ? C1 C2 C15 O4 176.76(12) . . . . ? C1 C2 C15 C14 60.03(16) . . . . ? C1 C2 C3 O2 -5.01(9) . . . . ? C1 C2 C3 C4 107.54(14) . . . . ? C1 O2 C3 C2 5.63(11) . . . . ? C1 O2 C3 C4 -116.00(12) . . . . ? C3 C2 C15 C6 36.16(16) . . . . ? C3 C2 C15 O4 -83.30(13) . . . . ? C3 C2 C15 C14 159.96(11) . . . . ? C3 C2 C1 O2 5.56(10) . . . . ? C3 C2 C1 O1 178.80(19) . . . . ? C3 O2 C1 C2 -5.73(11) . . . . ? C3 O2 C1 O1 179.58(15) . . . . ? C3 C4 C5 C6 -42.75(18) . . . . ? C8 C9 C10 C11 52.09(16) . . . . ? C8 C9 C10 C18 -126.56(15) . . . . ? C10 C9 C8 C7 -55.76(15) . . . . ? C10 C11 C19 C20 -114.93(16) . . . . ? C5 C6 C7 C12 -171.89(11) . . . . ? C5 C6 C7 C8 63.62(14) . . . . ? C5 C6 C15 C2 -57.66(14) . . . . ? C5 C6 C15 O4 57.45(13) . . . . ? C5 C6 C15 C14 176.30(11) . . . . ? C5 C4 C3 C2 18.9(2) . . . . ? C5 C4 C3 O2 119.49(13) . . . . ? C19 C11 C10 C9 -177.99(12) . . . . ? C19 C11 C10 C18 0.6(2) . . . . ?