#------------------------------------------------------------------------------ #$Date: 2018-01-15 12:18:40 +0200 (Mon, 15 Jan 2018) $ #$Revision: 205223 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548690.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_1548690 loop_ _publ_author_name 'Yulin Ren' 'Ulyana Munoz Acuna' 'Francisco Jimenez' 'Ricardo Garcia' 'Melciades Mejia' 'Heebyung Chai' 'Judith C. Gallucci' 'Norman R. Farnsworth' 'Djaja D. Soejarto' 'Esperanza J. Carcache de Blanco' 'A. Douglas Kinghorn' _publ_section_title ; Cytotoxic and NF-kB inhibitory sesquiterpene lactones from Piptocoma rufescens ; _journal_name_full Tetrahedron _journal_page_first 2671 _journal_page_last 2678 _journal_paper_doi 10.1016/j.tet.2012.01.061 _journal_volume 68 _journal_year 2012 _chemical_formula_sum 'C22 H30 O7' _chemical_formula_weight 406.46 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 5.5228(2) _cell_length_b 17.4103(7) _cell_length_c 22.1641(10) _cell_volume 2131.16(15) _diffrn_ambient_temperature 150 _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.88560 _exptl_absorpt_coefficient_mu 0.122 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_F_000 872 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_number_parameters 267 _refine_ls_number_reflns 4356 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0399 _refine_ls_wR_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.0880 _cod_data_source_file Tetrahedron-2012-68-2671.cif _cod_data_source_block 1 _cod_database_code 1548690 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 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 0.0250(10) 0.0330(10) 0.0410(10) 0.0040(10) 0.0020(10) 0.0070(10) O2 0.0260(10) 0.0330(10) 0.0220(10) 0.0040(10) 0.0020(10) 0.0020(10) O3 0.0550(10) 0.0240(10) 0.0330(10) -0.0040(10) 0.0170(10) -0.0040(10) O4 0.0770(10) 0.0330(10) 0.0400(10) -0.0020(10) 0.0300(10) 0.0030(10) O5 0.0250(10) 0.0160(10) 0.0320(10) 0.0010(10) 0.0000(10) 0.0010(10) O6 0.0260(10) 0.0320(10) 0.0580(10) 0.0110(10) 0.0020(10) 0.0030(10) O7 0.0380(10) 0.0400(10) 0.0280(10) 0.0060(10) -0.0030(10) 0.0050(10) C1 0.0280(10) 0.0280(10) 0.0230(10) 0.0070(10) -0.0010(10) 0.0020(10) C1' 0.0260(10) 0.0280(10) 0.0270(10) 0.0030(10) 0.0010(10) -0.0010(10) C1" 0.0330(10) 0.0310(10) 0.0250(10) 0.0020(10) -0.0030(10) -0.0040(10) C2 0.0310(10) 0.0230(10) 0.0300(10) 0.0060(10) 0.0020(10) 0.0000(10) C2' 0.0350(10) 0.0250(10) 0.0370(10) 0.0010(10) -0.0020(10) -0.0040(10) C2" 0.0370(10) 0.058(2) 0.0300(10) 0.0080(10) 0.0050(10) 0.0000(10) C3 0.0390(10) 0.0210(10) 0.0430(10) 0.0030(10) 0.0090(10) -0.0010(10) C3' 0.049(2) 0.0300(10) 0.052(2) 0.0050(10) 0.0010(10) -0.0050(10) C4 0.0420(10) 0.0290(10) 0.0380(10) -0.0040(10) 0.0080(10) -0.0120(10) C4' 0.060(2) 0.050(2) 0.062(2) 0.0090(10) 0.018(2) -0.0060(10) C5 0.0340(10) 0.0310(10) 0.0290(10) -0.0050(10) 0.0000(10) -0.0070(10) C5' 0.055(2) 0.0260(10) 0.064(2) -0.0090(10) 0.0060(10) 0.0010(10) C6 0.0340(10) 0.0240(10) 0.0240(10) -0.0020(10) 0.0030(10) 0.0000(10) C7 0.0260(10) 0.0210(10) 0.0250(10) 0.0010(10) 0.0000(10) 0.0020(10) C8 0.0270(10) 0.0140(10) 0.0280(10) 0.0010(10) 0.0000(10) 0.0020(10) C9 0.0240(10) 0.0200(10) 0.0240(10) 0.0000(10) 0.0000(10) 0.0020(10) C10 0.0220(10) 0.0240(10) 0.0220(10) 0.0020(10) 0.0020(10) 0.0000(10) C11 0.0310(10) 0.0260(10) 0.0230(10) 0.0000(10) 0.0010(10) 0.0020(10) C12 0.0440(10) 0.0290(10) 0.0320(10) 0.0010(10) 0.0050(10) 0.0020(10) C13 0.0460(10) 0.0290(10) 0.0220(10) 0.0010(10) 0.0020(10) 0.0030(10) C14 0.0300(10) 0.0330(10) 0.0300(10) -0.0010(10) -0.0040(10) -0.0040(10) C15 0.087(2) 0.0270(10) 0.051(2) -0.0110(10) 0.014(2) -0.0140(10) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uani 0.8616(3) -0.09340(10) -0.01150(10) 1.000 0.0330(6) . . . . O2 O Uani 0.3862(2) -0.00090(10) 0.06700(10) 1.000 0.0270(6) . . . . O3 O Uani 0.6275(3) -0.10200(10) -0.20050(10) 1.000 0.0373(6) . . . . O4 O Uani 0.8165(3) -0.05320(10) -0.28080(10) 1.000 0.0500(6) . . . . O5 O Uani 0.6412(2) 0.13090(10) -0.09620(10) 1.000 0.0243(6) . . . . O6 O Uani 1.0463(3) 0.12080(10) -0.10340(10) 1.000 0.0387(6) . . . . O7 O Uani 0.6071(3) -0.08160(10) 0.12360(10) 1.000 0.0353(6) . . . . C1 C Uani 0.6534(4) -0.08170(10) 0.00430(10) 1.000 0.0263(6) . . . . C1' C Uani 0.8670(4) 0.15980(10) -0.10320(10) 1.000 0.0270(6) . . . . C1" C Uani 0.4299(4) -0.04190(10) 0.11780(10) 1.000 0.0297(6) . . . . C2 C Uani 0.4642(4) -0.14470(10) 0.00170(10) 1.000 0.0280(6) . . . . C2' C Uani 0.8568(4) 0.24500(10) -0.11020(10) 1.000 0.0323(6) . . . . C2" C Uani 0.2316(4) -0.03280(10) 0.16260(10) 1.000 0.0417(8) . . . . C3 C Uani 0.5007(4) -0.20450(10) -0.04860(10) 1.000 0.0343(6) . . . . C3' C Uani 0.9971(5) 0.28020(10) -0.15040(10) 1.000 0.0437(10) . . . . C4 C Uani 0.3309(4) -0.19930(10) -0.10320(10) 1.000 0.0363(6) . . . . C4' C Uani 1.1706(5) 0.2464(2) -0.19380(10) 1.000 0.0573(12) . . . . C5 C Uani 0.3000(4) -0.11830(10) -0.12860(10) 1.000 0.0313(6) . . . . C5' C Uani 0.6814(5) 0.28680(10) -0.07030(10) 1.000 0.0483(10) . . . . C6 C Uani 0.5312(4) -0.07590(10) -0.14270(10) 1.000 0.0273(6) . . . . C7 C Uani 0.5125(4) 0.01320(10) -0.14670(10) 1.000 0.0240(6) . . . . C8 C Uani 0.6158(4) 0.04850(10) -0.08870(10) 1.000 0.0230(6) . . . . C9 C Uani 0.4524(3) 0.03600(10) -0.03340(10) 1.000 0.0227(6) . . . . C10 C Uani 0.5776(3) 0.00000(10) 0.02160(10) 1.000 0.0227(6) . . . . C11 C Uani 0.6481(4) 0.03090(10) -0.20410(10) 1.000 0.0267(6) . . . . C12 C Uani 0.7128(4) -0.04280(10) -0.23380(10) 1.000 0.0350(6) . . . . C13 C Uani 0.6938(4) 0.09720(10) -0.23080(10) 1.000 0.0323(6) . . . . C14 C Uani 0.7848(4) 0.04980(10) 0.04370(10) 1.000 0.0310(6) . . . . C15 C Uani 0.4149(6) -0.25680(10) -0.15120(10) 1.000 0.0550(10) . . . . H(2"1) H Uiso 0.08190 -0.05480 0.14630 1.000 0.0620 . . . . H(2"2) H Uiso 0.20710 0.02190 0.17110 1.000 0.0620 . . . . H2A H Uiso 0.30330 -0.12060 -0.00370 1.000 0.0330 . . . . H2B H Uiso 0.46270 -0.17170 0.04100 1.000 0.0330 . . . . H3' H Uiso 0.98410 0.33460 -0.15140 1.000 0.0530 . . . . H(2"3) H Uiso 0.27530 -0.05960 0.20000 1.000 0.0620 . . . . H3A H Uiso 0.66930 -0.20010 -0.06340 1.000 0.0410 . . . . H3B H Uiso 0.48280 -0.25630 -0.03060 1.000 0.0410 . . . . H4 H Uiso 0.16750 -0.21660 -0.08930 1.000 0.0430 . . . . H(4'1) H Uiso 1.15960 0.19030 -0.19220 1.000 0.0860 . . . . H(4'2) H Uiso 1.33540 0.26240 -0.18330 1.000 0.0860 . . . . H5A H Uiso 0.20260 -0.12160 -0.16600 1.000 0.0370 . . . . H5B H Uiso 0.20630 -0.08750 -0.09920 1.000 0.0370 . . . . H6 H Uiso 0.65220 -0.08880 -0.11070 1.000 0.0330 . . . . H(4'3) H Uiso 1.13180 0.26410 -0.23460 1.000 0.0860 . . . . H7 H Uiso 0.33900 0.02850 -0.15130 1.000 0.0290 . . . . H(5'1) H Uiso 0.69660 0.34220 -0.07690 1.000 0.0730 . . . . H8 H Uiso 0.77870 0.02560 -0.08050 1.000 0.0280 . . . . H(5'2) H Uiso 0.71690 0.27490 -0.02790 1.000 0.0730 . . . . H(5'3) H Uiso 0.51600 0.27040 -0.07980 1.000 0.0730 . . . . H9A H Uiso 0.38380 0.08620 -0.02130 1.000 0.0270 . . . . H9B H Uiso 0.31570 0.00250 -0.04540 1.000 0.0270 . . . . H13A H Uiso 0.76890 0.09810 -0.26930 1.000 0.0390 . . . . H13B H Uiso 0.65160 0.14400 -0.21140 1.000 0.0390 . . . . H14A H Uiso 0.72490 0.10170 0.05200 1.000 0.0460 . . . . H14B H Uiso 0.91080 0.05210 0.01260 1.000 0.0460 . . . . H14C H Uiso 0.85260 0.02770 0.08060 1.000 0.0460 . . . . H15A H Uiso 0.58050 -0.24430 -0.16370 1.000 0.0820 . . . . H15B H Uiso 0.30690 -0.25400 -0.18620 1.000 0.0820 . . . . H15C H Uiso 0.41100 -0.30890 -0.13440 1.000 0.0820 . . . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1" O2 C10 116.72(15) . . . yes C6 O3 C12 111.63(16) . . . yes C1' O5 C8 118.02(15) . . . yes O1 C1 C2 121.22(18) . . . yes O1 C1 C10 119.01(17) . . . yes C2 C1 C10 119.54(17) . . . no O5 C1' O6 123.37(18) . . . yes O5 C1' C2' 110.28(18) . . . yes O6 C1' C2' 126.4(2) . . . yes O2 C1" O7 122.4(2) . . . yes O2 C1" C2" 111.57(17) . . . yes O7 C1" C2" 126.0(2) . . . yes C1 C2 C3 115.27(18) . . . no C1' C2' C3' 120.36(19) . . . no C1' C2' C5' 116.44(18) . . . no C3' C2' C5' 123.20(17) . . . no C2 C3 C4 116.85(17) . . . no C2' C3' C4' 129.0(2) . . . no C3 C4 C5 114.42(16) . . . no C3 C4 C15 108.91(18) . . . no C5 C4 C15 112.39(18) . . . no C4 C5 C6 115.70(18) . . . no O3 C6 C5 109.76(16) . . . yes O3 C6 C7 106.52(17) . . . yes C5 C6 C7 116.32(17) . . . no C6 C7 C8 109.06(17) . . . no C6 C7 C11 102.63(16) . . . no C8 C7 C11 116.11(17) . . . no O5 C8 C7 109.63(17) . . . yes O5 C8 C9 106.74(16) . . . yes C7 C8 C9 113.13(17) . . . no C8 C9 C10 115.24(15) . . . no O2 C10 C1 111.14(16) . . . yes O2 C10 C9 103.04(14) . . . yes O2 C10 C14 109.26(17) . . . yes C1 C10 C9 107.67(17) . . . no C1 C10 C14 113.92(15) . . . no C9 C10 C14 111.27(15) . . . no C7 C11 C12 108.47(15) . . . no C7 C11 C13 130.63(18) . . . no C12 C11 C13 120.7(2) . . . no O3 C12 O4 121.60(18) . . . yes O3 C12 C11 109.43(19) . . . yes O4 C12 C11 128.93(19) . . . yes C1 C2 H2A 108.00 . . . no C1 C2 H2B 108.00 . . . no C3 C2 H2A 108.00 . . . no C3 C2 H2B 109.00 . . . no H2A C2 H2B 107.00 . . . no C1" C2" H(2"1) 109.00 . . . no C1" C2" H(2"2) 109.00 . . . no C1" C2" H(2"3) 109.00 . . . no H(2"1) C2" H(2"2) 110.00 . . . no H(2"1) C2" H(2"3) 109.00 . . . no H(2"2) C2" H(2"3) 109.00 . . . no C2 C3 H3A 108.00 . . . no C2 C3 H3B 108.00 . . . no C4 C3 H3A 108.00 . . . no C4 C3 H3B 108.00 . . . no H3A C3 H3B 107.00 . . . no C2' C3' H3' 116.00 . . . no C4' C3' H3' 115.00 . . . no C3 C4 H4 107.00 . . . no C5 C4 H4 107.00 . . . no C15 C4 H4 107.00 . . . no C3' C4' H(4'1) 109.00 . . . no C3' C4' H(4'2) 110.00 . . . no C3' C4' H(4'3) 109.00 . . . no H(4'1) C4' H(4'2) 109.00 . . . no H(4'1) C4' H(4'3) 109.00 . . . no H(4'2) C4' H(4'3) 109.00 . . . no C4 C5 H5A 108.00 . . . no C4 C5 H5B 108.00 . . . no C6 C5 H5A 108.00 . . . no C6 C5 H5B 108.00 . . . no H5A C5 H5B 107.00 . . . no C2' C5' H(5'1) 110.00 . . . no C2' C5' H(5'2) 109.00 . . . no C2' C5' H(5'3) 110.00 . . . no H(5'1) C5' H(5'2) 109.00 . . . no H(5'1) C5' H(5'3) 110.00 . . . no H(5'2) C5' H(5'3) 109.00 . . . no O3 C6 H6 108.00 . . . no C5 C6 H6 108.00 . . . no C7 C6 H6 108.00 . . . no C6 C7 H7 110.00 . . . no C8 C7 H7 110.00 . . . no C11 C7 H7 110.00 . . . no O5 C8 H8 109.00 . . . no C7 C8 H8 109.00 . . . no C9 C8 H8 109.00 . . . no C8 C9 H9A 108.00 . . . no C8 C9 H9B 108.00 . . . no C10 C9 H9A 109.00 . . . no C10 C9 H9B 108.00 . . . no H9A C9 H9B 108.00 . . . no C11 C13 H13A 120.00 . . . no C11 C13 H13B 120.00 . . . no H13A C13 H13B 120.00 . . . no C10 C14 H14A 109.00 . . . no C10 C14 H14B 109.00 . . . no C10 C14 H14C 110.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 110.00 . . . no H14B C14 H14C 109.00 . . . no C4 C15 H15A 109.00 . . . no C4 C15 H15B 109.00 . . . no C4 C15 H15C 110.00 . . . no H15A C15 H15B 109.00 . . . no H15A C15 H15C 109.00 . . . no H15B C15 H15C 109.00 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.219(3) . . yes O2 C1" 1.355(3) . . yes O2 C10 1.460(3) . . yes O3 C6 1.460(3) . . yes O3 C12 1.352(3) . . yes O4 C12 1.203(3) . . yes O5 C1' 1.354(2) . . yes O5 C8 1.451(2) . . yes O6 C1' 1.201(3) . . yes O7 C1" 1.205(3) . . yes C1 C2 1.516(3) . . no C1 C10 1.532(3) . . no C1' C2' 1.493(2) . . no C1" C2" 1.487(3) . . no C2 C3 1.539(3) . . no C2' C3' 1.330(3) . . no C2' C5' 1.500(3) . . no C3 C4 1.534(3) . . no C3' C4' 1.480(4) . . no C4 C5 1.528(3) . . no C4 C15 1.533(3) . . no C5 C6 1.508(3) . . no C6 C7 1.557(2) . . no C7 C8 1.535(3) . . no C7 C11 1.508(3) . . no C8 C9 1.538(3) . . no C9 C10 1.535(3) . . no C10 C14 1.517(3) . . no C11 C12 1.486(3) . . no C11 C13 1.322(3) . . no C2 H2A 0.9900 . . no C2 H2B 0.9900 . . no C2" H(2"1) 0.9800 . . no C2" H(2"2) 0.9800 . . no C2" H(2"3) 0.9800 . . no C3 H3A 0.9900 . . no C3 H3B 0.9900 . . no C3' H3' 0.9500 . . no C4 H4 1.0000 . . no C4' H(4'1) 0.9800 . . no C4' H(4'2) 0.9800 . . no C4' H(4'3) 0.9800 . . no C5 H5A 0.9900 . . no C5 H5B 0.9900 . . no C5' H(5'1) 0.9800 . . no C5' H(5'2) 0.9800 . . no C5' H(5'3) 0.9800 . . no C6 H6 1.0000 . . no C7 H7 1.0000 . . no C8 H8 1.0000 . . no C9 H9A 0.9900 . . no C9 H9B 0.9900 . . no C13 H13A 0.9500 . . no C13 H13B 0.9500 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no C15 H15A 0.9800 . . no C15 H15B 0.9800 . . no C15 H15C 0.9800 . . no 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 _geom_hbond_publ_flag C2 H2A O1 0.9900 2.4900 3.458(3) 165.00 1_455 yes C2 H2B O7 0.9900 2.5400 3.022(3) 110.00 . yes C3 H3A O1 0.9900 2.4300 2.897(3) 108.00 . yes C4' H(4'1) O6 0.9800 2.3900 3.044(4) 123.00 . yes C6 H6 O1 1.0000 2.4900 3.447(3) 161.00 . yes C7 H7 O6 1.0000 2.5100 3.326(3) 138.00 1_455 yes C8 H8 O6 1.0000 2.2800 2.710(3) 105.00 . yes C13 H13A O7 0.9500 2.4900 3.420(3) 168.00 2_654 yes C13 H13B O5 0.9500 2.5600 3.054(3) 112.00 . yes C14 H14C O7 0.9800 2.5200 3.055(3) 114.00 . yes C15 H15C O7 0.9800 2.5500 3.344(3) 138.00 3_445 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 O2 C1" C2" 175.00(16) . . . . no C1" O2 C10 C9 168.85(16) . . . . no C1" O2 C10 C14 -72.8(2) . . . . no C1" O2 C10 C1 53.8(2) . . . . no C10 O2 C1" O7 -6.6(3) . . . . no C6 O3 C12 C11 -8.1(2) . . . . no C12 O3 C6 C5 138.64(18) . . . . no C12 O3 C6 C7 11.9(2) . . . . no C6 O3 C12 O4 174.1(2) . . . . no C1' O5 C8 C7 -106.6(2) . . . . no C1' O5 C8 C9 130.5(2) . . . . no C8 O5 C1' C2' -180.0(2) . . . . no C8 O5 C1' O6 -0.1(4) . . . . no C2 C1 C10 C9 -76.4(2) . . . . no O1 C1 C2 C3 -30.6(3) . . . . no O1 C1 C10 C14 -25.8(3) . . . . no C2 C1 C10 C14 159.69(19) . . . . no C2 C1 C10 O2 35.8(3) . . . . no O1 C1 C10 O2 -149.7(2) . . . . no C10 C1 C2 C3 143.84(19) . . . . no O1 C1 C10 C9 98.1(2) . . . . no O6 C1' C2' C3' 41.3(4) . . . . no O6 C1' C2' C5' -139.1(3) . . . . no O5 C1' C2' C3' -138.8(2) . . . . no O5 C1' C2' C5' 40.7(3) . . . . no C1 C2 C3 C4 -105.5(2) . . . . no C1' C2' C3' C4' 1.9(4) . . . . no C5' C2' C3' C4' -177.7(2) . . . . no C2 C3 C4 C15 173.23(18) . . . . no C2 C3 C4 C5 46.5(3) . . . . no C3 C4 C5 C6 52.0(3) . . . . no C15 C4 C5 C6 -72.9(3) . . . . no C4 C5 C6 C7 -159.29(18) . . . . no C4 C5 C6 O3 79.7(2) . . . . no O3 C6 C7 C8 -134.18(18) . . . . no O3 C6 C7 C11 -10.5(2) . . . . no C5 C6 C7 C11 -133.18(19) . . . . no C5 C6 C7 C8 103.1(2) . . . . no C11 C7 C8 C9 173.22(16) . . . . no C6 C7 C11 C13 -179.7(2) . . . . no C8 C7 C11 C12 124.97(18) . . . . no C6 C7 C11 C12 6.1(2) . . . . no C6 C7 C8 C9 -71.5(2) . . . . no C6 C7 C8 O5 169.49(16) . . . . no C11 C7 C8 O5 54.2(2) . . . . no C8 C7 C11 C13 -60.8(3) . . . . no C7 C8 C9 C10 127.08(17) . . . . no O5 C8 C9 C10 -112.27(17) . . . . no C8 C9 C10 O2 177.01(15) . . . . no C8 C9 C10 C1 -65.46(19) . . . . no C8 C9 C10 C14 60.0(2) . . . . no C7 C11 C12 O3 0.7(2) . . . . no C13 C11 C12 O4 3.4(4) . . . . no C7 C11 C12 O4 178.3(2) . . . . no C13 C11 C12 O3 -174.2(2) . . . . no