#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012757.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012757 loop_ _publ_author_name 'Sun, Cui Rong' 'Shi, Hao' 'Pan, Yuan Jiang' _publ_section_title ; The natural diterpenoid kamebanin ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o323 _journal_page_last o324 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C20 H30 O4' _chemical_formula_moiety 'C20 H30 O4' _chemical_formula_sum 'C20 H30 O4' _chemical_formula_weight 334.44 _chemical_melting_point .539E-305 _chemical_name_common Kamebanin _chemical_name_systematic ; rel-(-)-(1R,4R,8S,9R,10S,13S,16R)-2,8,16-trihydroxy-5,5,9-trimethyl-14- methylenetetracyclo[11.2.1.0^1,10^.0^4,9^]hexadecan-15-one ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5680(10) _cell_length_b 13.282(3) _cell_length_c 20.801(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 289(2) _cell_measurement_theta_max 12.92 _cell_measurement_theta_min 3.06 _cell_volume 1814.6(7) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 289(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 2363 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 1.82 _diffrn_standards_decay_% 0.44 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.155 _refine_diff_density_min -0.156 _refine_ls_extinction_coef 0.0071(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 2176 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.927 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0447 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0514P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.1048 _reflns_number_gt 1446 _reflns_number_total 2176 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1200.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012757 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.3021(4) 0.11106(14) 0.33168(11) 0.0448(6) Uani d . 1 O H1O 0.2025 0.0824 0.3165 0.054 Uiso calc R 1 H O2 0.0783(4) 0.56849(15) 0.21511(11) 0.0467(6) Uani d . 1 O H2O 0.1697 0.5746 0.1886 0.056 Uiso calc R 1 H O3 0.3610(3) 0.50675(15) 0.13665(11) 0.0437(6) Uani d . 1 O H3O 0.4688 0.5358 0.1439 0.052 Uiso calc R 1 H O4 -0.1655(4) 0.37908(19) 0.15809(11) 0.0547(7) Uani d . 1 O C1 0.2431(5) 0.2081(2) 0.35526(14) 0.0376(7) Uani d . 1 C H1 0.0942 0.2094 0.3582 0.045 Uiso calc R 1 H C2 0.3286(6) 0.2169(2) 0.42323(14) 0.0495(9) Uani d . 1 C H2A 0.2853 0.1592 0.4484 0.059 Uiso calc R 1 H H2B 0.4761 0.2165 0.4215 0.059 Uiso calc R 1 H C3 0.2567(7) 0.3126(2) 0.45553(15) 0.0607(11) Uani d . 1 C H3A 0.3194 0.3172 0.4976 0.073 Uiso calc R 1 H H3B 0.1106 0.3085 0.4618 0.073 Uiso calc R 1 H C4 0.3050(6) 0.4090(3) 0.41797(16) 0.0499(9) Uani d . 1 C C5 0.2344(5) 0.3933(2) 0.34721(13) 0.0353(7) Uani d . 1 C H5 0.0874 0.3824 0.3512 0.042 Uiso calc R 1 H C6 0.2499(6) 0.4876(2) 0.30524(15) 0.0417(8) Uani d . 1 C H6A 0.2150 0.5468 0.3302 0.050 Uiso calc R 1 H H6B 0.3881 0.4954 0.2895 0.050 Uiso calc R 1 H C7 0.1042(5) 0.4762(2) 0.24928(14) 0.0336(7) Uani d . 1 C H7 -0.0288 0.4575 0.2670 0.040 Uiso calc R 1 H C8 0.1729(5) 0.3908(2) 0.20545(13) 0.0293(7) Uani d . 1 C C9 0.1884(4) 0.2898(2) 0.24561(13) 0.0306(7) Uani d . 1 C H9 0.0481 0.2750 0.2585 0.037 Uiso calc R 1 H C10 0.3109(4) 0.2964(2) 0.31095(13) 0.0295(7) Uani d . 1 C C11 0.2474(5) 0.2022(2) 0.19915(14) 0.0392(8) Uani d . 1 C H11A 0.3062 0.1484 0.2246 0.047 Uiso calc R 1 H H11B 0.1233 0.1763 0.1801 0.047 Uiso calc R 1 H C12 0.3958(6) 0.2271(2) 0.14481(15) 0.0484(9) Uani d . 1 C H12A 0.3896 0.1744 0.1125 0.058 Uiso calc R 1 H H12B 0.5333 0.2288 0.1618 0.058 Uiso calc R 1 H C13 0.3471(5) 0.3285(2) 0.11334(15) 0.0388(8) Uani d . 1 C H13 0.4375 0.3424 0.0769 0.047 Uiso calc R 1 H C14 0.3653(5) 0.4085(2) 0.16532(15) 0.0327(7) Uani d . 1 C H14 0.4886 0.3989 0.1911 0.039 Uiso calc R 1 H C15 0.0163(5) 0.3707(2) 0.15325(15) 0.0362(8) Uani d . 1 C C16 0.1270(5) 0.3354(2) 0.09450(15) 0.0430(9) Uani d . 1 C C17 0.0352(7) 0.3149(3) 0.03994(17) 0.0679(12) Uani d . 1 C H17A -0.1052 0.3222 0.0365 0.081 Uiso calc R 1 H H17B 0.1107 0.2932 0.0047 0.081 Uiso calc R 1 H C18 0.1781(8) 0.4934(3) 0.44865(17) 0.0789(14) Uani d . 1 C H18A 0.2229 0.5574 0.4324 0.095 Uiso calc R 1 H H18B 0.1952 0.4918 0.4945 0.095 Uiso calc R 1 H H18C 0.0370 0.4839 0.4383 0.095 Uiso calc R 1 H C19 0.5298(6) 0.4362(3) 0.42530(17) 0.0657(12) Uani d . 1 C H19A 0.6115 0.3771 0.4192 0.079 Uiso calc R 1 H H19B 0.5532 0.4628 0.4676 0.079 Uiso calc R 1 H H19C 0.5660 0.4859 0.3938 0.079 Uiso calc R 1 H C20 0.5413(4) 0.2926(2) 0.30027(15) 0.0397(8) Uani d . 1 C H20A 0.5729 0.2411 0.2695 0.048 Uiso calc R 1 H H20B 0.6082 0.2779 0.3402 0.048 Uiso calc R 1 H H20C 0.5875 0.3565 0.2844 0.048 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0499(15) 0.0299(11) 0.0545(14) -0.0030(11) -0.0133(13) 0.0028(11) O2 0.0508(15) 0.0356(11) 0.0538(14) 0.0128(12) -0.0023(12) 0.0065(11) O3 0.0401(14) 0.0413(12) 0.0498(13) -0.0078(11) -0.0037(12) 0.0139(11) O4 0.0311(14) 0.0787(18) 0.0543(15) -0.0050(13) -0.0040(12) -0.0034(14) C1 0.0377(17) 0.0335(15) 0.0418(18) -0.0071(16) -0.0035(16) -0.0002(15) C2 0.070(2) 0.0433(18) 0.0352(17) -0.013(2) -0.0089(18) 0.0131(16) C3 0.089(3) 0.062(2) 0.0304(17) -0.010(2) -0.005(2) -0.0019(17) C4 0.070(3) 0.045(2) 0.0352(17) -0.005(2) -0.0106(19) -0.0080(16) C5 0.0395(18) 0.0325(16) 0.0340(16) -0.0011(15) -0.0017(15) -0.0042(14) C6 0.048(2) 0.0334(16) 0.0436(18) 0.0047(17) -0.0053(18) -0.0039(15) C7 0.0312(16) 0.0301(15) 0.0395(17) 0.0032(14) -0.0007(16) 0.0022(13) C8 0.0276(16) 0.0265(15) 0.0338(15) 0.0010(13) -0.0014(14) -0.0007(13) C9 0.0318(15) 0.0287(14) 0.0315(15) -0.0037(15) -0.0003(14) 0.0000(13) C10 0.0303(16) 0.0282(14) 0.0300(15) -0.0009(14) -0.0029(13) 0.0017(14) C11 0.049(2) 0.0283(15) 0.0403(17) 0.0016(17) -0.0009(17) -0.0021(14) C12 0.056(2) 0.043(2) 0.0460(19) 0.0025(18) 0.0112(19) -0.0065(16) C13 0.045(2) 0.0412(18) 0.0306(15) -0.0040(16) 0.0118(16) -0.0015(14) C14 0.0272(16) 0.0328(16) 0.0381(17) 0.0001(13) 0.0021(15) 0.0057(14) C15 0.0315(18) 0.0375(17) 0.0394(18) -0.0047(14) -0.0010(15) 0.0092(16) C16 0.050(2) 0.0439(19) 0.0355(17) -0.0103(17) -0.0015(17) -0.0021(15) C17 0.064(3) 0.088(3) 0.051(2) -0.006(3) -0.004(2) -0.010(2) C18 0.119(4) 0.073(3) 0.045(2) 0.006(3) -0.010(3) -0.025(2) C19 0.090(3) 0.057(2) 0.051(2) -0.014(2) -0.029(2) 0.0020(19) C20 0.0363(18) 0.0366(16) 0.0461(18) -0.0017(16) -0.0077(16) 0.0045(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 O1 H1O 109.5 ? C7 O2 H2O 109.5 ? C14 O3 H3O 109.5 ? O1 C1 C2 106.7(2) ? O1 C1 C10 113.4(2) ? C2 C1 C10 112.7(2) ? O1 C1 H1 107.9 ? C2 C1 H1 107.9 ? C10 C1 H1 107.9 ? C3 C2 C1 111.2(3) ? C3 C2 H2A 109.4 ? C1 C2 H2A 109.4 ? C3 C2 H2B 109.4 ? C1 C2 H2B 109.4 ? H2A C2 H2B 108.0 ? C2 C3 C4 114.3(3) ? C2 C3 H3A 108.7 ? C4 C3 H3A 108.7 ? C2 C3 H3B 108.7 ? C4 C3 H3B 108.7 ? H3A C3 H3B 107.6 ? C19 C4 C3 110.3(3) ? C19 C4 C18 108.1(3) ? C3 C4 C18 106.6(3) ? C19 C4 C5 114.4(3) ? C3 C4 C5 107.9(3) ? C18 C4 C5 109.2(3) ? C6 C5 C4 114.2(2) ? C6 C5 C10 112.0(2) ? C4 C5 C10 117.9(3) ? C6 C5 H5 103.5 ? C4 C5 H5 103.5 ? C10 C5 H5 103.5 ? C7 C6 C5 108.4(3) ? C7 C6 H6A 110.0 ? C5 C6 H6A 110.0 ? C7 C6 H6B 110.0 ? C5 C6 H6B 110.0 ? H6A C6 H6B 108.4 ? O2 C7 C6 111.9(2) ? O2 C7 C8 112.1(2) ? C6 C7 C8 110.3(2) ? O2 C7 H7 107.4 ? C6 C7 H7 107.4 ? C8 C7 H7 107.4 ? C15 C8 C7 111.0(3) ? C15 C8 C14 101.3(2) yes C7 C8 C14 117.1(2) yes C15 C8 C9 105.8(2) ? C7 C8 C9 109.5(2) ? C14 C8 C9 111.4(2) ? C11 C9 C10 116.5(2) ? C11 C9 C8 108.7(2) ? C10 C9 C8 116.1(2) ? C11 C9 H9 104.7 ? C10 C9 H9 104.7 ? C8 C9 H9 104.7 ? C20 C10 C1 110.1(3) ? C20 C10 C5 114.3(3) ? C1 C10 C5 104.0(2) ? C20 C10 C9 112.1(3) ? C1 C10 C9 108.8(2) ? C5 C10 C9 107.1(2) ? C12 C11 C9 117.1(2) ? C12 C11 H11A 108.0 ? C9 C11 H11A 108.0 ? C12 C11 H11B 108.0 ? C9 C11 H11B 108.0 ? H11A C11 H11B 107.3 ? C11 C12 C13 111.9(3) ? C11 C12 H12A 109.2 ? C13 C12 H12A 109.2 ? C11 C12 H12B 109.2 ? C13 C12 H12B 109.2 ? H12A C12 H12B 107.9 ? C16 C13 C14 102.6(3) yes C16 C13 C12 111.5(3) ? C14 C13 C12 107.1(3) ? C16 C13 H13 111.7 ? C14 C13 H13 111.7 ? C12 C13 H13 111.7 ? O3 C14 C13 109.8(2) ? O3 C14 C8 110.5(2) ? C13 C14 C8 102.4(2) ? O3 C14 H14 111.3 ? C13 C14 H14 111.3 ? C8 C14 H14 111.3 ? O4 C15 C16 125.4(3) yes O4 C15 C8 126.6(3) yes C16 C15 C8 108.0(3) yes C17 C16 C15 123.2(3) yes C17 C16 C13 130.9(3) yes C15 C16 C13 105.9(3) yes C16 C17 H17A 120.0 ? C16 C17 H17B 120.0 ? H17A C17 H17B 120.0 ? C4 C18 H18A 109.5 ? C4 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? C4 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? C4 C19 H19A 109.5 ? C4 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C4 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? C10 C20 H20A 109.5 ? C10 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? C10 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.432(3) yes O1 H1O 0.8200 ? O2 C7 1.427(3) yes O2 H2O 0.8200 ? O3 C14 1.435(3) yes O3 H3O 0.8200 ? O4 C15 1.204(4) yes C1 C2 1.526(4) ? C1 C10 1.557(4) ? C1 H1 0.9800 ? C2 C3 1.514(4) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.533(4) ? C3 H3A 0.9700 ? C3 H3B 0.9700 ? C4 C19 1.528(5) ? C4 C18 1.536(5) ? C4 C5 1.557(4) ? C5 C6 1.530(4) ? C5 C10 1.574(4) ? C5 H5 0.9800 ? C6 C7 1.515(4) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.524(4) ? C7 H7 0.9800 ? C8 C15 1.519(4) yes C8 C14 1.533(4) yes C8 C9 1.583(4) ? C9 C11 1.561(4) ? C9 C10 1.582(4) ? C9 H9 0.9800 ? C10 C20 1.531(4) ? C11 C12 1.528(4) ? C11 H11A 0.9700 ? C11 H11B 0.9700 ? C12 C13 1.531(4) ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 C16 1.501(5) yes C13 C14 1.521(4) yes C13 H13 0.9800 ? C14 H14 0.9800 ? C15 C16 1.497(4) yes C16 C17 1.313(5) yes C17 H17A 0.9300 ? C17 H17B 0.9300 ? C18 H18A 0.9600 ? C18 H18B 0.9600 ? C18 H18C 0.9600 ? C19 H19A 0.9600 ? C19 H19B 0.9600 ? C19 H19C 0.9600 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H2O O3 . 0.82 1.89 2.605(3) 146 yes O1 H1O O2 3_545 0.82 1.97 2.741(3) 157 yes O3 H3O O1 3_655 0.82 1.88 2.692(3) 173 yes 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 O1 C1 C2 C3 -174.1(3) C10 C1 C2 C3 60.8(4) C1 C2 C3 C4 -55.6(4) C2 C3 C4 C19 -76.4(4) C2 C3 C4 C18 166.5(3) C2 C3 C4 C5 49.3(4) C19 C4 C5 C6 -63.5(4) C3 C4 C5 C6 173.3(3) C18 C4 C5 C6 57.8(4) C19 C4 C5 C10 71.1(4) C3 C4 C5 C10 -52.1(4) C18 C4 C5 C10 -167.6(3) C4 C5 C6 C7 -157.3(3) C10 C5 C6 C7 65.4(3) C5 C6 C7 O2 168.1(3) C5 C6 C7 C8 -66.3(3) O2 C7 C8 C15 -60.9(3) C6 C7 C8 C15 173.7(2) O2 C7 C8 C14 54.7(3) C6 C7 C8 C14 -70.7(3) O2 C7 C8 C9 -177.3(2) C6 C7 C8 C9 57.3(3) C15 C8 C9 C11 57.3(3) C7 C8 C9 C11 176.9(2) C14 C8 C9 C11 -51.9(3) C15 C8 C9 C10 -169.0(2) C7 C8 C9 C10 -49.4(3) C14 C8 C9 C10 81.8(3) O1 C1 C10 C20 -55.9(3) C2 C1 C10 C20 65.5(3) O1 C1 C10 C5 -178.7(3) C2 C1 C10 C5 -57.4(3) O1 C1 C10 C9 67.4(3) C2 C1 C10 C9 -171.3(3) C6 C5 C10 C20 70.9(3) C4 C5 C10 C20 -64.6(4) C6 C5 C10 C1 -169.0(3) C4 C5 C10 C1 55.5(3) C6 C5 C10 C9 -53.9(3) C4 C5 C10 C9 170.5(3) C11 C9 C10 C20 50.5(3) C8 C9 C10 C20 -79.6(3) C11 C9 C10 C1 -71.6(3) C8 C9 C10 C1 158.4(2) C11 C9 C10 C5 176.6(2) C8 C9 C10 C5 46.6(3) C10 C9 C11 C12 -96.9(3) C8 C9 C11 C12 36.5(4) C9 C11 C12 C13 -42.2(4) C11 C12 C13 C16 -50.9(3) C11 C12 C13 C14 60.7(3) C16 C13 C14 O3 -73.7(3) C12 C13 C14 O3 168.7(3) C16 C13 C14 C8 43.6(3) C12 C13 C14 C8 -73.9(3) C15 C8 C14 O3 76.2(3) C7 C8 C14 O3 -44.6(3) C9 C8 C14 O3 -171.7(2) C15 C8 C14 C13 -40.7(3) C7 C8 C14 C13 -161.5(2) C9 C8 C14 C13 71.4(3) C7 C8 C15 O4 -33.4(4) C14 C8 C15 O4 -158.4(3) C9 C8 C15 O4 85.3(4) C7 C8 C15 C16 148.2(2) C14 C8 C15 C16 23.1(3) C9 C8 C15 C16 -93.1(3) O4 C15 C16 C17 4.0(5) C8 C15 C16 C17 -177.5(3) O4 C15 C16 C13 -175.0(3) C8 C15 C16 C13 3.5(3) C14 C13 C16 C17 152.1(4) C12 C13 C16 C17 -93.5(4) C14 C13 C16 C15 -29.0(3) C12 C13 C16 C15 85.4(3)