#------------------------------------------------------------------------------ #$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301775 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507744.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_1507744 loop_ _publ_author_name 'Liu, Xiaozu' 'Lee, Chi-Sing' _publ_section_title ; Total synthesis of (-)-teucvidin. ; _journal_issue 11 _journal_name_full 'Organic letters' _journal_page_first 2886 _journal_page_last 2889 _journal_paper_doi 10.1021/ol301098s _journal_volume 14 _journal_year 2012 _chemical_formula_sum 'C17 H22 O4' _chemical_formula_weight 290.35 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 84.347(7) _cell_angle_beta 73.511(7) _cell_angle_gamma 68.007(5) _cell_formula_units_Z 2 _cell_length_a 8.2806(6) _cell_length_b 8.7559(2) _cell_length_c 11.7722(2) _cell_measurement_reflns_used 8614 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 62.30 _cell_measurement_theta_min 6.70 _cell_volume 758.84(7) _computing_cell_refinement 'CrystalClear-SM 2.0 r4' _computing_data_collection 'CrystalClear-SM 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM 2.0 r4' _computing_molecular_graphics 'CrystalStructure 4.0 (Rigaku, 2009)' _computing_publication_material 'CrystalStructure 4.0' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Rigaku Saturn944 CCD' _diffrn_measurement_method \w _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 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9233 _diffrn_reflns_theta_full 59.99 _diffrn_reflns_theta_max 59.99 _diffrn_reflns_theta_min 6.69 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_T_max 0.9646 _exptl_absorpt_correction_T_min 0.7126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.405 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2228 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0555 _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^)+(0.0500P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1269 _refine_ls_wR_factor_ref 0.1381 _reflns_number_gt 1756 _reflns_number_total 2228 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL liu in P-1 CELL 1.54178 8.2806 8.7559 11.7722 84.347 73.511 68.007 ZERR 2.00 0.0006 0.0002 0.0002 0.007 0.007 0.005 LATT 1 SFAC C H O UNIT 34 44 8 TEMP 24 SIZE 0.5 0.3 0.05 ACTA OMIT -2 120 OMIT 2 -2 13 OMIT 7 8 2 OMIT 7 -3 6 OMIT 8 7 5 OMIT 8 7 6 OMIT 6 8 7 OMIT 7 8 8 OMIT 9 7 3 OMIT 5 10 0 OMIT 2 -3 12 OMIT 8 8 1 OMIT 6 -5 3 OMIT 5 9 3 OMIT 6 8 2 OMIT 8 7 4 OMIT 8 8 2 OMIT 6 -5 4 OMIT 6 -4 3 OMIT -5 -10 1 OMIT 7 7 4 OMIT 5 9 8 OMIT 6 7 11 BOND $H CONF L.S. 5 FMAP 2 PLAN 20 WGHT 0.050000 0.500000 FVAR 0.48837 O1 3 0.31171 0.82033 0.45387 11.00000 0.08462 0.08491 = 0.04264 -0.00097 -0.01870 -0.02998 O2 3 0.16458 1.05786 0.37521 11.00000 0.11939 0.12364 = 0.05980 0.02469 -0.04398 -0.03875 O3 3 0.28662 0.64644 1.00647 11.00000 0.12894 0.09491 = 0.07533 0.04262 -0.06181 -0.07703 O4 3 0.37623 0.85741 0.96817 11.00000 0.09073 0.06822 = 0.05745 0.01440 -0.04057 -0.04663 C1 1 0.37256 0.77275 0.56012 11.00000 0.05529 0.06490 = 0.03906 -0.00358 -0.01189 -0.01891 AFIX 13 H1 2 0.50498 0.73094 0.53857 11.00000 -1.20000 AFIX 0 C2 1 0.30695 0.64519 0.63252 11.00000 0.06033 0.05021 = 0.04940 -0.01136 -0.01108 -0.01930 AFIX 23 H2A 2 0.36360 0.54084 0.59002 11.00000 -1.20000 H2B 2 0.17710 0.67957 0.64643 11.00000 -1.20000 AFIX 0 C3 1 0.35508 0.62530 0.75090 11.00000 0.05352 0.04207 = 0.05038 0.00098 -0.01558 -0.01941 AFIX 13 H3 2 0.30828 0.54381 0.79644 11.00000 -1.20000 AFIX 0 C4 1 0.25776 0.78922 0.82423 11.00000 0.04781 0.04163 = 0.03862 0.00333 -0.01361 -0.02084 C5 1 0.31097 0.93337 0.75345 11.00000 0.04761 0.04528 = 0.04271 0.00183 -0.01302 -0.02209 AFIX 13 H5 2 0.43692 0.91194 0.75087 11.00000 -1.20000 AFIX 0 C6 1 0.19651 1.10888 0.80344 11.00000 0.07009 0.04543 = 0.05351 -0.00125 -0.01452 -0.02525 AFIX 23 H6B 2 0.07134 1.11825 0.83404 11.00000 -1.20000 H6A 2 0.23694 1.12628 0.86910 11.00000 -1.20000 AFIX 0 C7 1 0.20717 1.24226 0.71281 11.00000 0.08555 0.05235 = 0.07649 0.00625 -0.01426 -0.02810 AFIX 23 H7B 2 0.33199 1.23383 0.68184 11.00000 -1.20000 H7A 2 0.13811 1.34936 0.75065 11.00000 -1.20000 AFIX 0 C8 1 0.13287 1.22740 0.61002 11.00000 0.07425 0.06055 = 0.06739 0.01884 -0.01819 -0.01914 AFIX 23 H8B 2 0.00257 1.25887 0.63686 11.00000 -1.20000 H8A 2 0.16120 1.29972 0.54599 11.00000 -1.20000 AFIX 0 C9 1 0.21813 1.05330 0.56806 11.00000 0.05778 0.06349 = 0.04783 0.01177 -0.01547 -0.02666 C10 1 0.30142 0.92840 0.62907 11.00000 0.04571 0.05408 = 0.04187 0.00326 -0.00807 -0.02391 C11 1 0.22347 0.98789 0.45645 11.00000 0.07034 0.09121 = 0.04702 0.01509 -0.01967 -0.03202 C12 1 0.56001 0.55620 0.73398 11.00000 0.05497 0.05721 = 0.07204 -0.00124 -0.01921 -0.01158 AFIX 33 H12C 2 0.61311 0.45672 0.68753 11.00000 -1.50000 H12B 2 0.58506 0.53285 0.80993 11.00000 -1.50000 H12A 2 0.61023 0.63575 0.69389 11.00000 -1.50000 AFIX 0 C13 1 0.30838 0.75535 0.94163 11.00000 0.05112 0.04926 = 0.04641 0.00364 -0.01723 -0.02462 C14 1 0.42262 0.83052 1.08010 11.00000 0.10657 0.08674 = 0.06207 0.01572 -0.05081 -0.05185 AFIX 33 H14C 2 0.47111 0.91059 1.09025 11.00000 -1.50000 H14B 2 0.51122 0.72189 1.08060 11.00000 -1.50000 H14A 2 0.31629 0.84125 1.14364 11.00000 -1.50000 AFIX 0 C15 1 0.04863 0.83671 0.85542 11.00000 0.05082 0.04759 = 0.04183 0.00133 -0.01260 -0.02079 AFIX 23 H15A 2 -0.00694 0.92227 0.91591 11.00000 -1.20000 H15B 2 0.00899 0.88384 0.78549 11.00000 -1.20000 AFIX 0 C16 1 -0.02192 0.70095 0.89826 11.00000 0.05489 0.05444 = 0.05343 0.00735 -0.01358 -0.02787 AFIX 43 H16 2 0.01579 0.63658 0.96029 11.00000 -1.20000 AFIX 0 C17 1 -0.13203 0.66724 0.85464 11.00000 0.07440 0.07104 = 0.08583 0.01752 -0.03151 -0.04283 AFIX 93 H17B 2 -0.17235 0.72924 0.79256 11.00000 -1.20000 H17A 2 -0.17073 0.58105 0.88542 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _cod_data_source_file ol301098s_si_002.cif _cod_data_source_block liu _cod_original_cell_volume 758.84(6) _cod_database_code 1507744 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 0.3117(3) 0.8203(3) 0.45387(15) 0.0700(5) Uani 1 1 d . O2 O 0.1646(4) 1.0579(3) 0.37519(19) 0.0994(8) Uani 1 1 d . O3 O 0.2866(3) 0.6464(3) 1.00648(18) 0.0838(7) Uani 1 1 d . O4 O 0.3762(3) 0.8574(2) 0.96816(15) 0.0628(5) Uani 1 1 d . C1 C 0.3726(3) 0.7727(3) 0.56012(19) 0.0534(6) Uani 1 1 d . H1 H 0.5050 0.7309 0.5386 0.064 Uiso 1 1 calc R C2 C 0.3070(3) 0.6452(3) 0.6325(2) 0.0531(6) Uani 1 1 d . H2A H 0.3636 0.5408 0.5900 0.064 Uiso 1 1 calc R H2B H 0.1771 0.6795 0.6464 0.064 Uiso 1 1 calc R C3 C 0.3551(3) 0.6253(3) 0.7509(2) 0.0473(6) Uani 1 1 d . H3 H 0.3083 0.5438 0.7964 0.057 Uiso 1 1 calc R C4 C 0.2577(3) 0.7892(3) 0.82423(18) 0.0407(5) Uani 1 1 d . C5 C 0.3110(3) 0.9334(3) 0.75345(18) 0.0431(5) Uani 1 1 d . H5 H 0.4369 0.9119 0.7509 0.052 Uiso 1 1 calc R C6 C 0.1965(4) 1.1089(3) 0.8035(2) 0.0549(6) Uani 1 1 d . H6B H 0.0713 1.1183 0.8341 0.066 Uiso 1 1 calc R H6A H 0.2369 1.1263 0.8691 0.066 Uiso 1 1 calc R C7 C 0.2071(4) 1.2423(3) 0.7128(3) 0.0721(8) Uani 1 1 d . H7B H 0.3320 1.2339 0.6818 0.087 Uiso 1 1 calc R H7A H 0.1381 1.3494 0.7506 0.087 Uiso 1 1 calc R C8 C 0.1329(4) 1.2274(3) 0.6100(3) 0.0701(8) Uani 1 1 d . H8B H 0.0026 1.2589 0.6368 0.084 Uiso 1 1 calc R H8A H 0.1612 1.2997 0.5460 0.084 Uiso 1 1 calc R C9 C 0.2181(3) 1.0533(3) 0.5681(2) 0.0551(6) Uani 1 1 d . C10 C 0.3014(3) 0.9284(3) 0.62908(19) 0.0461(5) Uani 1 1 d . C11 C 0.2235(4) 0.9879(4) 0.4565(2) 0.0685(8) Uani 1 1 d . C12 C 0.5600(3) 0.5562(3) 0.7340(2) 0.0630(7) Uani 1 1 d . H12C H 0.6131 0.4567 0.6875 0.094 Uiso 1 1 calc R H12B H 0.5851 0.5328 0.8099 0.094 Uiso 1 1 calc R H12A H 0.6103 0.6357 0.6939 0.094 Uiso 1 1 calc R C13 C 0.3084(3) 0.7553(3) 0.9416(2) 0.0459(5) Uani 1 1 d . C14 C 0.4226(5) 0.8305(4) 1.0801(2) 0.0745(8) Uani 1 1 d . H14C H 0.4711 0.9106 1.0903 0.112 Uiso 1 1 calc R H14B H 0.5112 0.7219 1.0806 0.112 Uiso 1 1 calc R H14A H 0.3163 0.8413 1.1437 0.112 Uiso 1 1 calc R C15 C 0.0486(3) 0.8367(3) 0.85542(19) 0.0455(5) Uani 1 1 d . H15A H -0.0070 0.9223 0.9159 0.055 Uiso 1 1 calc R H15B H 0.0090 0.8839 0.7855 0.055 Uiso 1 1 calc R C16 C -0.0219(3) 0.7010(3) 0.8983(2) 0.0521(6) Uani 1 1 d . H16 H 0.0158 0.6366 0.9603 0.063 Uiso 1 1 calc R C17 C -0.1320(4) 0.6672(4) 0.8546(3) 0.0707(8) Uani 1 1 d . H17B H -0.1724 0.7292 0.7925 0.085 Uiso 1 1 calc R H17A H -0.1708 0.5810 0.8854 0.085 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 0.0842(13) 0.0844(14) 0.0422(10) -0.0009(9) -0.0186(9) -0.0298(11) O2 0.1190(19) 0.1231(19) 0.0593(13) 0.0247(13) -0.0439(13) -0.0386(15) O3 0.1284(18) 0.0944(15) 0.0749(13) 0.0426(12) -0.0617(13) -0.0768(14) O4 0.0902(13) 0.0678(11) 0.0570(10) 0.0144(8) -0.0404(9) -0.0464(10) C1 0.0550(14) 0.0645(15) 0.0387(12) -0.0035(11) -0.0118(10) -0.0188(12) C2 0.0600(14) 0.0498(13) 0.0490(13) -0.0113(10) -0.0110(11) -0.0192(11) C3 0.0531(13) 0.0417(12) 0.0500(13) 0.0009(10) -0.0155(10) -0.0193(10) C4 0.0474(12) 0.0412(12) 0.0383(11) 0.0033(9) -0.0135(9) -0.0207(10) C5 0.0472(12) 0.0448(12) 0.0423(12) 0.0018(9) -0.0129(10) -0.0219(10) C6 0.0696(16) 0.0450(13) 0.0531(14) -0.0012(10) -0.0144(12) -0.0251(12) C7 0.085(2) 0.0519(15) 0.0761(19) 0.0063(13) -0.0143(15) -0.0280(14) C8 0.0738(18) 0.0601(16) 0.0669(17) 0.0188(13) -0.0181(14) -0.0189(14) C9 0.0574(14) 0.0630(15) 0.0474(14) 0.0118(11) -0.0154(11) -0.0265(12) C10 0.0453(12) 0.0536(13) 0.0414(12) 0.0032(10) -0.0079(10) -0.0237(11) C11 0.0699(17) 0.091(2) 0.0467(15) 0.0150(14) -0.0195(13) -0.0319(16) C12 0.0545(15) 0.0567(15) 0.0716(17) -0.0012(13) -0.0191(13) -0.0114(12) C13 0.0507(13) 0.0489(13) 0.0460(13) 0.0036(10) -0.0171(10) -0.0245(11) C14 0.106(2) 0.086(2) 0.0616(17) 0.0157(14) -0.0507(16) -0.0517(18) C15 0.0504(13) 0.0472(12) 0.0414(12) 0.0014(9) -0.0125(10) -0.0207(10) C16 0.0545(14) 0.0540(14) 0.0530(14) 0.0073(11) -0.0134(11) -0.0277(12) C17 0.0740(18) 0.0706(18) 0.085(2) 0.0176(15) -0.0314(16) -0.0427(15) 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 C11 O1 C1 108.41(19) C13 O4 C14 116.35(19) O1 C1 C10 104.59(19) O1 C1 C2 114.0(2) C10 C1 C2 110.48(18) O1 C1 H1 109.2 C10 C1 H1 109.2 C2 C1 H1 109.2 C1 C2 C3 108.89(19) C1 C2 H2A 109.9 C3 C2 H2A 109.9 C1 C2 H2B 109.9 C3 C2 H2B 109.9 H2A C2 H2B 108.3 C2 C3 C12 111.8(2) C2 C3 C4 111.07(18) C12 C3 C4 112.92(19) C2 C3 H3 106.9 C12 C3 H3 106.9 C4 C3 H3 106.9 C13 C4 C15 106.44(17) C13 C4 C3 107.10(17) C15 C4 C3 109.97(17) C13 C4 C5 112.55(17) C15 C4 C5 109.66(17) C3 C4 C5 110.98(17) C10 C5 C6 108.40(18) C10 C5 C4 108.39(17) C6 C5 C4 116.43(18) C10 C5 H5 107.8 C6 C5 H5 107.8 C4 C5 H5 107.8 C7 C6 C5 113.4(2) C7 C6 H6B 108.9 C5 C6 H6B 108.9 C7 C6 H6A 108.9 C5 C6 H6A 108.9 H6B C6 H6A 107.7 C6 C7 C8 111.2(2) C6 C7 H7B 109.4 C8 C7 H7B 109.4 C6 C7 H7A 109.4 C8 C7 H7A 109.4 H7B C7 H7A 108.0 C9 C8 C7 108.1(2) C9 C8 H8B 110.1 C7 C8 H8B 110.1 C9 C8 H8A 110.1 C7 C8 H8A 110.1 H8B C8 H8A 108.4 C10 C9 C11 108.0(2) C10 C9 C8 124.3(2) C11 C9 C8 127.6(2) C9 C10 C1 110.0(2) C9 C10 C5 126.9(2) C1 C10 C5 122.87(19) O2 C11 O1 120.9(3) O2 C11 C9 130.3(3) O1 C11 C9 108.9(2) C3 C12 H12C 109.5 C3 C12 H12B 109.5 H12C C12 H12B 109.5 C3 C12 H12A 109.5 H12C C12 H12A 109.5 H12B C12 H12A 109.5 O3 C13 O4 121.8(2) O3 C13 C4 123.2(2) O4 C13 C4 114.95(18) O4 C14 H14C 109.5 O4 C14 H14B 109.5 H14C C14 H14B 109.5 O4 C14 H14A 109.5 H14C C14 H14A 109.5 H14B C14 H14A 109.5 C16 C15 C4 116.72(18) C16 C15 H15A 108.1 C4 C15 H15A 108.1 C16 C15 H15B 108.1 C4 C15 H15B 108.1 H15A C15 H15B 107.3 C17 C16 C15 124.3(2) C17 C16 H16 117.8 C15 C16 H16 117.8 C16 C17 H17B 120.0 C16 C17 H17A 120.0 H17B C17 H17A 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.371(4) O1 C1 1.446(3) O2 C11 1.206(3) O3 C13 1.197(3) O4 C13 1.320(3) O4 C14 1.449(3) C1 C10 1.486(3) C1 C2 1.508(3) C1 H1 0.9800 C2 C3 1.532(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 C12 1.533(3) C3 C4 1.562(3) C3 H3 0.9800 C4 C13 1.526(3) C4 C15 1.561(3) C4 C5 1.576(3) C5 C10 1.494(3) C5 C6 1.542(3) C5 H5 0.9800 C6 C7 1.513(3) C6 H6B 0.9700 C6 H6A 0.9700 C7 C8 1.540(4) C7 H7B 0.9700 C7 H7A 0.9700 C8 C9 1.487(4) C8 H8B 0.9700 C8 H8A 0.9700 C9 C10 1.323(3) C9 C11 1.467(4) C12 H12C 0.9600 C12 H12B 0.9600 C12 H12A 0.9600 C14 H14C 0.9600 C14 H14B 0.9600 C14 H14A 0.9600 C15 C16 1.498(3) C15 H15A 0.9700 C15 H15B 0.9700 C16 C17 1.296(4) C16 H16 0.9300 C17 H17B 0.9300 C17 H17A 0.9300 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 O1 C1 C10 3.3(3) C11 O1 C1 C2 124.1(2) O1 C1 C2 C3 -171.28(19) C10 C1 C2 C3 -53.8(3) C1 C2 C3 C12 -64.7(2) C1 C2 C3 C4 62.5(2) C2 C3 C4 C13 177.96(18) C12 C3 C4 C13 -55.5(2) C2 C3 C4 C15 62.7(2) C12 C3 C4 C15 -170.79(19) C2 C3 C4 C5 -58.8(2) C12 C3 C4 C5 67.7(2) C13 C4 C5 C10 165.45(18) C15 C4 C5 C10 -76.3(2) C3 C4 C5 C10 45.4(2) C13 C4 C5 C6 -72.1(2) C15 C4 C5 C6 46.2(2) C3 C4 C5 C6 167.90(19) C10 C5 C6 C7 -36.8(3) C4 C5 C6 C7 -159.3(2) C5 C6 C7 C8 62.3(3) C6 C7 C8 C9 -49.0(3) C7 C8 C9 C10 16.9(4) C7 C8 C9 C11 -164.3(2) C11 C9 C10 C1 1.8(3) C8 C9 C10 C1 -179.2(2) C11 C9 C10 C5 -172.6(2) C8 C9 C10 C5 6.4(4) O1 C1 C10 C9 -3.2(3) C2 C1 C10 C9 -126.3(2) O1 C1 C10 C5 171.47(19) C2 C1 C10 C5 48.4(3) C6 C5 C10 C9 3.3(3) C4 C5 C10 C9 130.6(2) C6 C5 C10 C1 -170.4(2) C4 C5 C10 C1 -43.2(3) C1 O1 C11 O2 177.8(3) C1 O1 C11 C9 -2.4(3) C10 C9 C11 O2 -179.8(3) C8 C9 C11 O2 1.2(5) C10 C9 C11 O1 0.3(3) C8 C9 C11 O1 -178.6(2) C14 O4 C13 O3 -0.1(4) C14 O4 C13 C4 178.9(2) C15 C4 C13 O3 63.1(3) C3 C4 C13 O3 -54.5(3) C5 C4 C13 O3 -176.8(2) C15 C4 C13 O4 -115.9(2) C3 C4 C13 O4 126.5(2) C5 C4 C13 O4 4.3(3) C13 C4 C15 C16 -71.3(2) C3 C4 C15 C16 44.4(2) C5 C4 C15 C16 166.71(18) C4 C15 C16 C17 -128.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 60149344