#------------------------------------------------------------------------------ #$Date: 2013-03-19 10:04:47 +0200 (Tue, 19 Mar 2013) $ #$Revision: 76459 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/88/4118893.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4118893 loop_ _publ_author_name 'Michael W. Lodewyk' 'Cristian Soldi' 'Paul B. Jones' 'Marilyn M. Olmstead' 'Juan Rita' 'Jared T. Shaw' 'Dean J. Tantillo' _publ_section_title ; The Correct Structure of Aquatolide-Experimental Validation of a Theoretically-Predicted Structural Revision ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 18550 _journal_page_last 18553 _journal_volume 134 _journal_year 2012 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H18 O3' _chemical_formula_sum 'C15 H18 O3' _chemical_formula_weight 246.29 _chemical_name_systematic ; ? ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _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 109.978(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.3980(12) _cell_length_b 6.1397(8) _cell_length_c 11.6079(16) _cell_measurement_reflns_used 6491 _cell_measurement_temperature 90(2) _cell_measurement_theta_max 72.2 _cell_measurement_theta_min 5.26 _cell_volume 629.48(14) _computing_cell_refinement 'SAINT (Bruker, 2011)' _computing_data_collection 'Apex2 (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 90(2) _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker DUO' _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6731 _diffrn_reflns_theta_full 67.73 _diffrn_reflns_theta_max 67.73 _diffrn_reflns_theta_min 5.26 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.299 _exptl_crystal_description plate _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.218 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2238 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0268 _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^)+(0.0430P)^2^+0.1092P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.0712 _reflns_number_gt 2219 _reflns_number_total 2238 _reflns_threshold_expression I>2\s(I) _journal_paper_doi 10.1021/ja3089394 _iucr_refine_instructions_details ; TITL mn2118 in P2(1) Cristian Soldi CS3143.3 CELL 1.54178 9.3980 6.1397 11.6079 90.000 109.978 90.000 ZERR 2.00 0.0012 0.0008 0.0016 0.000 0.004 0.000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H O UNIT 30 36 6 TEMP -183 acta size 0.02 0.06 0.12 omit -3 0 1 omit 0 0 1 omit 1 2 1 omit 0 0 2 omit 0 -1 1 L.S. 8 conf bond $h EQIV $1 x, y-1, z HTAB C11 O1_$1 WGHT 0.043000 0.109200 FVAR 0.55657 O1 3 0.664107 0.721300 0.493769 11.00000 0.03587 0.02135 = 0.02298 -0.00704 0.01568 -0.00697 O2 3 0.406702 0.306181 -0.018556 11.00000 0.02527 0.02052 = 0.01617 -0.00100 0.00862 -0.00063 O3 3 0.737315 0.373300 0.499318 11.00000 0.02687 0.02072 = 0.01403 -0.00005 0.00712 -0.00291 C1 1 0.660757 0.551452 0.441471 11.00000 0.02248 0.02015 = 0.01746 -0.00135 0.01043 -0.00530 C2 1 0.572915 0.488623 0.309941 11.00000 0.01970 0.01486 = 0.01649 -0.00068 0.00873 -0.00218 C3 1 0.439338 0.637807 0.246902 11.00000 0.02464 0.01637 = 0.01806 0.00098 0.00997 0.00194 H3A 2 0.468134 0.784188 0.283617 11.00000 0.02682 H3B 2 0.430807 0.656329 0.158993 11.00000 0.01288 C4 1 0.290619 0.563447 0.260616 11.00000 0.02329 0.02037 = 0.02102 0.00077 0.01138 0.00503 H4A 2 0.218558 0.687971 0.237581 11.00000 0.02790 H4B 2 0.304766 0.522535 0.343872 11.00000 0.02087 C5 1 0.211563 0.376480 0.181422 11.00000 0.01820 0.02814 = 0.02299 0.00109 0.00864 0.00105 H5 2 0.108738 0.342227 0.184936 11.00000 0.02500 C6 1 0.254075 0.253605 0.104422 11.00000 0.01685 0.02587 = 0.01817 0.00025 0.00550 0.00082 C7 1 0.403475 0.273525 0.083867 11.00000 0.02113 0.01406 = 0.01615 -0.00323 0.00785 -0.00107 C8 1 0.549990 0.219542 0.186627 11.00000 0.01810 0.01560 = 0.01645 -0.00156 0.00850 -0.00108 H8 2 0.588623 0.086349 0.162309 11.00000 0.01478 C9 1 0.667685 0.407845 0.226374 11.00000 0.01923 0.01796 = 0.01417 -0.00035 0.00855 -0.00152 H9 2 0.686085 0.509025 0.166345 11.00000 0.01097 C10 1 0.805724 0.291944 0.318156 11.00000 0.01752 0.01769 = 0.01715 0.00065 0.00551 -0.00077 C11 1 0.719286 0.209465 0.403843 11.00000 0.02132 0.01640 = 0.01624 0.00028 0.00590 -0.00031 H11 2 0.752947 0.068122 0.448243 11.00000 0.01907 C12 1 0.552306 0.237735 0.319434 11.00000 0.01986 0.01461 = 0.01521 0.00089 0.00838 -0.00036 H12 2 0.475404 0.179717 0.350368 11.00000 0.01959 C13 1 0.150644 0.085604 0.022558 11.00000 0.02107 0.03449 = 0.02862 -0.00627 0.01036 -0.00646 AFIX 137 H13A 2 0.059888 0.069195 0.045240 11.00000 -1.20000 H13B 2 0.203654 -0.054314 0.032349 11.00000 -1.20000 H13C 2 0.121271 0.132912 -0.063040 11.00000 -1.20000 AFIX 0 C14 1 0.867061 0.100248 0.263740 11.00000 0.01816 0.02374 = 0.02329 -0.00158 0.00713 0.00174 AFIX 137 H14A 2 0.877258 0.144874 0.185874 11.00000 -1.20000 H14B 2 0.796753 -0.022832 0.249549 11.00000 -1.20000 H14C 2 0.966256 0.056553 0.321122 11.00000 -1.20000 AFIX 0 C15 1 0.935747 0.450788 0.378037 11.00000 0.02003 0.02536 = 0.02129 -0.00207 0.00685 -0.00396 AFIX 137 H15A 2 0.985121 0.489863 0.318968 11.00000 -1.20000 H15B 2 1.009601 0.381647 0.449771 11.00000 -1.20000 H15C 2 0.895692 0.582462 0.403674 11.00000 -1.20000 HKLF 4 REM mn2118 in P2(1) Cristian Soldi CS3143.3 REM R1 = 0.0268 for 2219 Fo > 4sig(Fo) and 0.0280 for all 2238 data REM 202 parameters refined using 1 restraints END WGHT 0.0404 0.1132 REM Highest difference peak 0.218, deepest hole -0.169, 1-sigma level 0.032 Q1 1 0.6352 0.2012 0.3624 11.00000 0.05 0.22 Q2 1 0.5404 0.2128 0.2457 11.00000 0.05 0.20 Q3 1 0.4791 0.2505 0.1438 11.00000 0.05 0.19 Q4 1 0.7439 0.3557 0.2650 11.00000 0.05 0.17 Q5 1 0.5016 0.5559 0.2755 11.00000 0.05 0.17 Q6 1 0.6333 0.4543 0.2743 11.00000 0.05 0.16 Q7 1 0.7720 0.2523 0.3646 11.00000 0.05 0.16 Q8 1 0.6151 0.5388 0.3675 11.00000 0.05 0.15 Q9 1 0.3644 0.6173 0.2570 11.00000 0.05 0.14 Q10 1 0.8783 0.3710 0.3524 11.00000 0.05 0.13 Q11 1 0.3275 0.2599 0.0979 11.00000 0.05 0.13 Q12 1 0.2570 0.2791 0.1687 11.00000 0.05 0.12 Q13 1 0.2037 0.4184 0.1137 11.00000 0.05 0.12 Q14 1 0.1975 0.1864 0.0627 11.00000 0.05 0.10 Q15 1 0.6086 0.2979 0.1958 11.00000 0.05 0.10 Q16 1 0.5248 0.0690 0.4809 11.00000 0.05 0.10 Q17 1 0.7520 0.7243 0.5637 11.00000 0.05 0.09 Q18 1 0.0440 0.1491 -0.0169 11.00000 0.05 0.09 Q19 1 0.7319 0.2973 0.4549 11.00000 0.05 0.09 Q20 1 0.7688 -0.2142 0.1778 11.00000 0.05 0.09 ; _[local]_cod_data_source_file ja3089394_si_002.cif _[local]_cod_data_source_block mn2118 _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_database_code 4118893 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 O1 O 0.66411(11) 0.72130(17) 0.49377(8) 0.0253(2) Uani 1 1 d . O2 O 0.40670(10) 0.30618(15) -0.01856(8) 0.0203(2) Uani 1 1 d . O3 O 0.73732(10) 0.37330(16) 0.49932(7) 0.0205(2) Uani 1 1 d . C1 C 0.66076(15) 0.5515(2) 0.44147(12) 0.0191(3) Uani 1 1 d . C2 C 0.57291(14) 0.4886(2) 0.30994(11) 0.0164(3) Uani 1 1 d . C3 C 0.43934(14) 0.6378(2) 0.24690(11) 0.0190(3) Uani 1 1 d . H3A H 0.4681(19) 0.784(3) 0.2836(16) 0.027(4) Uiso 1 1 d . H3B H 0.4308(16) 0.656(3) 0.1590(14) 0.013(3) Uiso 1 1 d . C4 C 0.29062(15) 0.5634(2) 0.26062(12) 0.0206(3) Uani 1 1 d . H4A H 0.2186(19) 0.688(3) 0.2376(16) 0.028(4) Uiso 1 1 d . H4B H 0.3048(18) 0.523(3) 0.3439(15) 0.021(4) Uiso 1 1 d . C5 C 0.21156(14) 0.3765(3) 0.18142(12) 0.0227(3) Uani 1 1 d . H5 H 0.109(2) 0.342(3) 0.1849(15) 0.025(4) Uiso 1 1 d . C6 C 0.25407(14) 0.2536(2) 0.10442(11) 0.0204(3) Uani 1 1 d . C7 C 0.40348(14) 0.2735(2) 0.08387(11) 0.0167(3) Uani 1 1 d . C8 C 0.54999(13) 0.2195(2) 0.18663(11) 0.0160(2) Uani 1 1 d . H8 H 0.5886(16) 0.086(3) 0.1623(13) 0.015(3) Uiso 1 1 d . C9 C 0.66769(13) 0.4078(2) 0.22637(11) 0.0164(3) Uani 1 1 d . H9 H 0.6861(16) 0.509(3) 0.1663(13) 0.011(3) Uiso 1 1 d . C10 C 0.80572(13) 0.2919(2) 0.31816(11) 0.0176(3) Uani 1 1 d . C11 C 0.71929(14) 0.2095(2) 0.40384(11) 0.0181(3) Uani 1 1 d . H11 H 0.7529(17) 0.068(3) 0.4482(14) 0.019(4) Uiso 1 1 d . C12 C 0.55231(13) 0.2377(2) 0.31943(11) 0.0159(3) Uani 1 1 d . H12 H 0.4754(17) 0.180(3) 0.3504(13) 0.020(4) Uiso 1 1 d . C13 C 0.15064(15) 0.0856(3) 0.02256(13) 0.0276(3) Uani 1 1 d . H13A H 0.0599 0.0692 0.0452 0.033 Uiso 1 1 calc R H13B H 0.2037 -0.0543 0.0323 0.033 Uiso 1 1 calc R H13C H 0.1213 0.1329 -0.0630 0.033 Uiso 1 1 calc R C14 C 0.86706(14) 0.1002(2) 0.26374(12) 0.0217(3) Uani 1 1 d . H14A H 0.8773 0.1449 0.1859 0.026 Uiso 1 1 calc R H14B H 0.7968 -0.0228 0.2495 0.026 Uiso 1 1 calc R H14C H 0.9663 0.0566 0.3211 0.026 Uiso 1 1 calc R C15 C 0.93575(14) 0.4508(2) 0.37804(12) 0.0223(3) Uani 1 1 d . H15A H 0.9851 0.4899 0.3190 0.027 Uiso 1 1 calc R H15B H 1.0096 0.3816 0.4498 0.027 Uiso 1 1 calc R H15C H 0.8957 0.5825 0.4037 0.027 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 0.0359(5) 0.0214(5) 0.0230(5) -0.0070(4) 0.0157(4) -0.0070(4) O2 0.0253(4) 0.0205(5) 0.0162(4) -0.0010(3) 0.0086(3) -0.0006(4) O3 0.0269(5) 0.0207(5) 0.0140(4) 0.0000(4) 0.0071(3) -0.0029(4) C1 0.0225(6) 0.0202(7) 0.0175(6) -0.0014(5) 0.0104(5) -0.0053(5) C2 0.0197(6) 0.0149(6) 0.0165(6) -0.0007(5) 0.0087(5) -0.0022(5) C3 0.0246(7) 0.0164(6) 0.0181(6) 0.0010(5) 0.0100(5) 0.0019(5) C4 0.0233(6) 0.0204(7) 0.0210(7) 0.0008(5) 0.0114(5) 0.0050(5) C5 0.0182(6) 0.0281(7) 0.0230(6) 0.0011(6) 0.0086(5) 0.0010(6) C6 0.0168(6) 0.0259(7) 0.0182(6) 0.0003(5) 0.0055(5) 0.0008(5) C7 0.0211(6) 0.0141(6) 0.0162(6) -0.0032(4) 0.0079(5) -0.0011(4) C8 0.0181(6) 0.0156(6) 0.0164(6) -0.0016(5) 0.0085(5) -0.0011(5) C9 0.0192(6) 0.0180(7) 0.0142(5) -0.0003(5) 0.0085(4) -0.0015(5) C10 0.0175(6) 0.0177(6) 0.0172(6) 0.0007(5) 0.0055(5) -0.0008(5) C11 0.0213(6) 0.0164(6) 0.0162(6) 0.0003(5) 0.0059(5) -0.0003(5) C12 0.0199(6) 0.0146(6) 0.0152(6) 0.0009(5) 0.0084(5) -0.0004(5) C13 0.0211(6) 0.0345(9) 0.0286(7) -0.0063(6) 0.0104(5) -0.0065(6) C14 0.0182(6) 0.0237(7) 0.0233(6) -0.0016(6) 0.0071(5) 0.0017(5) C15 0.0200(6) 0.0254(7) 0.0213(6) -0.0021(5) 0.0069(5) -0.0040(5) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O3 C11 105.98(9) O1 C1 O3 122.18(11) O1 C1 C2 129.84(13) O3 C1 C2 107.93(11) C1 C2 C3 113.97(11) C1 C2 C12 102.59(10) C3 C2 C12 121.68(11) C1 C2 C9 117.64(10) C3 C2 C9 115.60(10) C12 C2 C9 81.11(9) C2 C3 C4 113.75(11) C2 C3 H3A 106.2(10) C4 C3 H3A 110.5(10) C2 C3 H3B 108.9(8) C4 C3 H3B 112.4(8) H3A C3 H3B 104.5(14) C5 C4 C3 116.34(11) C5 C4 H4A 105.9(10) C3 C4 H4A 107.7(10) C5 C4 H4B 106.6(10) C3 C4 H4B 111.4(10) H4A C4 H4B 108.5(14) C6 C5 C4 130.25(12) C6 C5 H5 115.0(10) C4 C5 H5 114.7(10) C5 C6 C7 124.74(12) C5 C6 C13 122.23(12) C7 C6 C13 112.95(11) O2 C7 C6 120.25(11) O2 C7 C8 119.01(11) C6 C7 C8 120.10(10) C7 C8 C12 118.02(10) C7 C8 C9 115.62(11) C12 C8 C9 83.32(9) C7 C8 H8 106.4(8) C12 C8 H8 118.2(8) C9 C8 H8 114.3(9) C10 C9 C8 101.93(10) C10 C9 C2 103.58(9) C8 C9 C2 85.63(9) C10 C9 H9 117.8(8) C8 C9 H9 122.3(8) C2 C9 H9 119.8(9) C15 C10 C14 108.71(10) C15 C10 C9 111.83(11) C14 C10 C9 114.46(10) C15 C10 C11 115.06(10) C14 C10 C11 111.20(11) C9 C10 C11 95.24(9) O3 C11 C12 103.42(10) O3 C11 C10 107.91(10) C12 C11 C10 101.24(9) O3 C11 H11 105.7(9) C12 C11 H11 119.7(9) C10 C11 H11 117.7(9) C8 C12 C11 106.86(9) C8 C12 C2 87.74(9) C11 C12 C2 91.83(10) C8 C12 H12 125.6(9) C11 C12 H12 116.3(9) C2 C12 H12 120.7(10) C6 C13 H13A 109.5 C6 C13 H13B 109.5 H13A C13 H13B 109.5 C6 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C10 C14 H14A 109.5 C10 C14 H14B 109.5 H14A C14 H14B 109.5 C10 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C10 C15 H15A 109.5 C10 C15 H15B 109.5 H15A C15 H15B 109.5 C10 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2016(17) O2 C7 1.2163(15) O3 C1 1.3546(17) O3 C11 1.4630(16) C1 C2 1.5166(17) C2 C3 1.5240(17) C2 C12 1.5611(17) C2 C9 1.6033(16) C3 C4 1.5295(18) C3 H3A 0.99(2) C3 H3B 1.002(15) C4 C5 1.499(2) C4 H4A 0.995(19) C4 H4B 0.963(17) C5 C6 1.3310(19) C5 H5 1.003(17) C6 C7 1.5074(17) C6 C13 1.5102(18) C7 C8 1.5187(16) C8 C12 1.5384(16) C8 C9 1.5570(17) C8 H8 0.975(17) C9 C10 1.5427(16) C9 H9 0.992(15) C10 C15 1.5320(17) C10 C14 1.5380(18) C10 C11 1.5677(17) C11 C12 1.5499(16) C11 H11 1.004(17) C12 H12 0.977(16) C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C11 H11 O1 1.004(17) 2.411(18) 3.2729(17) 143.5(12) 1_545 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 C11 O3 C1 O1 -173.86(11) C11 O3 C1 C2 8.53(12) O1 C1 C2 C3 -18.81(19) O3 C1 C2 C3 158.55(10) O1 C1 C2 C12 -152.30(13) O3 C1 C2 C12 25.06(12) O1 C1 C2 C9 121.24(14) O3 C1 C2 C9 -61.40(14) C1 C2 C3 C4 -90.68(13) C12 C2 C3 C4 33.00(16) C9 C2 C3 C4 128.42(11) C2 C3 C4 C5 -76.60(15) C3 C4 C5 C6 4.3(2) C4 C5 C6 C7 2.8(2) C4 C5 C6 C13 -173.68(14) C5 C6 C7 O2 -123.27(15) C13 C6 C7 O2 53.49(17) C5 C6 C7 C8 65.93(18) C13 C6 C7 C8 -117.31(13) O2 C7 C8 C12 164.31(11) C6 C7 C8 C12 -24.78(17) O2 C7 C8 C9 68.04(15) C6 C7 C8 C9 -121.05(12) C7 C8 C9 C10 -173.50(10) C12 C8 C9 C10 68.56(9) C7 C8 C9 C2 83.53(11) C12 C8 C9 C2 -34.41(8) C1 C2 C9 C10 32.42(14) C3 C2 C9 C10 171.84(10) C12 C2 C9 C10 -67.19(10) C1 C2 C9 C8 133.66(11) C3 C2 C9 C8 -86.92(11) C12 C2 C9 C8 34.04(8) C8 C9 C10 C15 -175.99(10) C2 C9 C10 C15 -87.66(12) C8 C9 C10 C14 59.83(12) C2 C9 C10 C14 148.16(10) C8 C9 C10 C11 -56.31(10) C2 C9 C10 C11 32.01(11) C1 O3 C11 C12 -39.72(12) C1 O3 C11 C10 67.00(12) C15 C10 C11 O3 25.24(14) C14 C10 C11 O3 149.38(10) C9 C10 C11 O3 -91.83(10) C15 C10 C11 C12 133.48(11) C14 C10 C11 C12 -102.39(11) C9 C10 C11 C12 16.40(11) C7 C8 C12 C11 -171.36(11) C9 C8 C12 C11 -55.83(10) C7 C8 C12 C2 -80.13(12) C9 C8 C12 C2 35.39(8) O3 C11 C12 C8 138.77(9) C10 C11 C12 C8 27.06(13) O3 C11 C12 C2 50.58(10) C10 C11 C12 C2 -61.12(10) C1 C2 C12 C8 -150.93(9) C3 C2 C12 C8 80.24(12) C9 C2 C12 C8 -34.43(8) C1 C2 C12 C11 -44.13(10) C3 C2 C12 C11 -172.95(11) C9 C2 C12 C11 72.37(9)