#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151774.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_7151774 loop_ _publ_author_name 'Schanderl, Martin' 'Jeong, Won Boo' 'Schwarz, Michael' 'Reiser, Oliver' _publ_section_title ; Stereoselective rearrangement of guaianolides to tricyclic \d-valerolactones. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2543 _journal_page_last 2547 _journal_volume 9 _journal_year 2011 _chemical_absolute_configuration syn _chemical_compound_source 'see text' _chemical_formula_moiety 'C16 H22 O5' _chemical_formula_sum 'C16 H22 O5' _chemical_formula_weight 294.34 _chemical_name_systematic ; ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.7923(7) _cell_length_b 11.6086(14) _cell_length_c 20.037(3) _cell_measurement_reflns_used 4824 _cell_measurement_temperature 297 _cell_measurement_theta_max 25.93 _cell_measurement_theta_min 2.03 _cell_volume 1579.9(3) _computing_cell_refinement 'STOE (1998)' _computing_data_collection 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _diffrn_ambient_temperature 297(1) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1121 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 13786 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.93 _diffrn_reflns_theta_max 25.93 _diffrn_reflns_theta_min 2.03 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_type none _exptl_crystal_colour 'translucent colourless' _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description stick _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.520 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.159 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.0(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3068 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.785 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0439 _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^)+(0.0217P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.0946 _reflns_number_gt 1455 _reflns_number_total 3068 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file c0ob00919a.txt _[local]_cod_data_source_block i206 _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_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7151774 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_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 0.0709(14) 0.0657(16) 0.0744(15) -0.0069(13) 0.0155(12) -0.0095(12) O2 0.0874(17) 0.0629(17) 0.0921(19) -0.0011(14) 0.0207(15) -0.0145(15) O3 0.0650(14) 0.124(2) 0.0823(18) -0.0377(17) 0.0068(14) 0.0011(16) O4 0.0601(13) 0.0862(18) 0.0554(13) -0.0099(13) 0.0062(12) -0.0101(12) O5 0.0572(13) 0.106(2) 0.0725(15) -0.0084(15) 0.0080(13) 0.0003(14) C1 0.0596(19) 0.060(2) 0.064(2) 0.006(2) 0.0028(18) -0.0033(19) C2 0.0552(19) 0.069(2) 0.065(2) 0.0028(19) 0.0007(16) -0.0039(17) C3 0.0503(17) 0.065(2) 0.0527(19) 0.0060(17) -0.0032(15) 0.0000(16) C4 0.0478(17) 0.069(2) 0.055(2) 0.0008(18) 0.0020(15) 0.0052(16) C5 0.0506(17) 0.065(2) 0.058(2) 0.0010(17) 0.0030(16) -0.0029(16) C6 0.0516(19) 0.070(2) 0.060(2) 0.0007(18) 0.0055(16) 0.0067(16) C7 0.058(2) 0.078(3) 0.061(2) -0.013(2) -0.0034(17) 0.0076(18) C8 0.058(2) 0.083(3) 0.065(2) -0.012(2) -0.0045(18) 0.0023(19) C9 0.0538(17) 0.064(2) 0.060(2) -0.0059(18) -0.0053(17) 0.0007(17) C10 0.0537(18) 0.060(2) 0.069(2) 0.0053(18) -0.0035(17) -0.0026(17) C11 0.066(2) 0.071(2) 0.065(2) 0.0041(18) 0.0028(19) -0.0073(19) C12 0.060(2) 0.066(2) 0.0468(18) -0.0007(16) -0.0012(15) 0.0004(17) C13 0.073(2) 0.096(3) 0.078(3) -0.012(2) 0.009(2) 0.004(2) C14 0.069(2) 0.074(3) 0.087(3) -0.001(2) -0.001(2) -0.009(2) C15 0.0577(19) 0.074(2) 0.072(2) -0.007(2) 0.0110(19) -0.0106(19) C16 0.113(3) 0.138(4) 0.088(3) -0.048(3) 0.029(3) -0.033(3) 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 O1 O Uani -0.3441(3) -0.0144(2) 0.16766(11) 1.000 0.0703(9) . . O2 O Uani -0.3816(4) -0.1777(2) 0.11574(13) 1.000 0.0808(10) . . O3 O Uani -0.2363(3) 0.3075(3) 0.31752(13) 1.000 0.0904(10) . . O4 O Uani 0.1994(3) 0.0200(2) -0.00540(11) 1.000 0.0672(9) . . O5 O Uani 0.5269(3) 0.0187(2) 0.00407(12) 1.000 0.0786(9) . . C1 C Uani -0.2833(5) -0.0901(3) 0.12105(17) 1.000 0.0612(11) . . C2 C Uani -0.1012(5) -0.0678(3) 0.08216(18) 1.000 0.0631(11) . . C3 C Uani -0.0280(4) 0.0562(3) 0.08340(16) 1.000 0.0560(11) . . C4 C Uani -0.0469(4) 0.1015(3) 0.15484(16) 1.000 0.0573(11) . . C5 C Uani -0.2613(4) 0.1006(3) 0.17335(16) 1.000 0.0579(11) . . C6 C Uani -0.2984(4) 0.1417(3) 0.24469(16) 1.000 0.0605(11) . . C7 C Uani -0.2215(4) 0.2648(3) 0.25109(16) 1.000 0.0657(14) . . C8 C Uani -0.0066(5) 0.2741(3) 0.23178(16) 1.000 0.0687(14) . . C9 C Uani 0.0447(5) 0.2190(3) 0.16536(17) 1.000 0.0593(11) . . C10 C Uani 0.1760(4) 0.2623(3) 0.12256(18) 1.000 0.0609(11) . . C11 C Uani 0.2333(5) 0.1979(3) 0.05895(17) 1.000 0.0673(12) . . C12 C Uani 0.1807(4) 0.0711(3) 0.06087(15) 1.000 0.0576(11) . . C13 C Uani -0.5145(5) 0.1298(4) 0.26436(19) 1.000 0.0823(16) . . C14 C Uani 0.2867(5) 0.3728(3) 0.1312(2) 1.000 0.0767(16) . . C15 C Uani 0.3816(5) -0.0052(3) -0.02593(17) 1.000 0.0679(11) . . C16 C Uani 0.3764(7) -0.0671(4) -0.0919(2) 1.000 0.1130(19) . . H2A H Uiso -0.12480 -0.08960 0.03610 1.000 0.0760 calc R H2B H Uiso 0.00240 -0.11720 0.09920 1.000 0.0760 calc R H3 H Uiso -0.11310 0.10250 0.05440 1.000 0.0670 calc R H3A H Uiso -0.35260 0.31170 0.32820 1.000 0.1080 calc R H4 H Uiso 0.02100 0.04710 0.18430 1.000 0.0690 calc R H5 H Uiso -0.33210 0.15170 0.14270 1.000 0.0700 calc R H6 H Uiso -0.22090 0.09290 0.27470 1.000 0.0730 calc R H7 H Uiso -0.29880 0.31470 0.22160 1.000 0.0790 calc R H8A H Uiso 0.07220 0.23820 0.26640 1.000 0.0820 calc R H8B H Uiso 0.02910 0.35490 0.23010 1.000 0.0820 calc R H11A H Uiso 0.16750 0.23350 0.02120 1.000 0.0810 calc R H11B H Uiso 0.37400 0.20560 0.05210 1.000 0.0810 calc R H12 H Uiso 0.26880 0.03120 0.09190 1.000 0.0690 calc R H13A H Uiso -0.55390 0.05070 0.26040 1.000 0.0990 calc R H13B H Uiso -0.59400 0.17650 0.23540 1.000 0.0990 calc R H13C H Uiso -0.53160 0.15480 0.30970 1.000 0.0990 calc R H14A H Uiso 0.36420 0.36910 0.17120 1.000 0.0920 calc R H14B H Uiso 0.19530 0.43560 0.13430 1.000 0.0920 calc R H14C H Uiso 0.37170 0.38450 0.09350 1.000 0.0920 calc R H16A H Uiso 0.31410 -0.01900 -0.12470 1.000 0.1360 calc R H16B H Uiso 0.30330 -0.13750 -0.08720 1.000 0.1360 calc R H16C H Uiso 0.50830 -0.08440 -0.10580 1.000 0.1360 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? 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 O1 C5 122.4(2) . . . yes C12 O4 C15 116.7(2) . . . yes C7 O3 H3A 109.00 . . . no O1 C1 O2 115.9(3) . . . yes O1 C1 C2 120.4(3) . . . yes O2 C1 C2 123.7(3) . . . yes C1 C2 C3 115.4(3) . . . no C2 C3 C12 114.4(3) . . . no C4 C3 C12 108.8(2) . . . no C2 C3 C4 108.2(3) . . . no C3 C4 C5 108.0(2) . . . no C5 C4 C9 111.7(3) . . . no C3 C4 C9 113.9(3) . . . no O1 C5 C4 111.2(3) . . . yes C4 C5 C6 112.9(2) . . . no O1 C5 C6 107.3(2) . . . yes C5 C6 C7 108.3(3) . . . no C5 C6 C13 111.8(3) . . . no C7 C6 C13 113.1(3) . . . no O3 C7 C6 112.3(3) . . . yes O3 C7 C8 106.4(2) . . . yes C6 C7 C8 112.0(3) . . . no C7 C8 C9 114.6(3) . . . no C4 C9 C10 121.6(3) . . . no C8 C9 C10 123.9(3) . . . no C4 C9 C8 114.1(3) . . . no C9 C10 C14 125.7(3) . . . no C11 C10 C14 112.8(3) . . . no C9 C10 C11 121.4(3) . . . no C10 C11 C12 113.2(3) . . . no O4 C12 C11 110.6(3) . . . yes C3 C12 C11 110.1(3) . . . no O4 C12 C3 108.0(2) . . . yes O4 C15 C16 110.7(3) . . . yes O5 C15 C16 125.1(3) . . . yes O4 C15 O5 124.2(3) . . . yes C1 C2 H2A 108.00 . . . no C1 C2 H2B 108.00 . . . no C3 C2 H2A 108.00 . . . no C3 C2 H2B 108.00 . . . no H2A C2 H2B 107.00 . . . no C2 C3 H3 108.00 . . . no C4 C3 H3 108.00 . . . no C12 C3 H3 108.00 . . . no C3 C4 H4 108.00 . . . no C5 C4 H4 108.00 . . . no C9 C4 H4 108.00 . . . no O1 C5 H5 108.00 . . . no C4 C5 H5 108.00 . . . no C6 C5 H5 108.00 . . . no C5 C6 H6 108.00 . . . no C7 C6 H6 108.00 . . . no C13 C6 H6 108.00 . . . no O3 C7 H7 109.00 . . . no C6 C7 H7 109.00 . . . no C8 C7 H7 109.00 . . . no C7 C8 H8A 109.00 . . . no C7 C8 H8B 109.00 . . . no C9 C8 H8A 109.00 . . . no C9 C8 H8B 109.00 . . . no H8A C8 H8B 108.00 . . . no C10 C11 H11A 109.00 . . . no C10 C11 H11B 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no O4 C12 H12 109.00 . . . no C3 C12 H12 109.00 . . . no C11 C12 H12 109.00 . . . no C6 C13 H13A 109.00 . . . no C6 C13 H13B 109.00 . . . no C6 C13 H13C 109.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no C10 C14 H14A 109.00 . . . no C10 C14 H14B 109.00 . . . no C10 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no C15 C16 H16A 109.00 . . . no C15 C16 H16B 109.00 . . . no C15 C16 H16C 109.00 . . . no H16A C16 H16B 109.00 . . . no H16A C16 H16C 110.00 . . . no H16B C16 H16C 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 1.347(4) . . yes O1 C5 1.453(4) . . yes O2 C1 1.221(4) . . yes O3 C7 1.424(4) . . yes O4 C12 1.460(4) . . yes O4 C15 1.337(4) . . yes O5 C15 1.188(4) . . yes O3 H3A 0.8200 . . no C1 C2 1.485(5) . . no C2 C3 1.523(5) . . no C3 C12 1.498(4) . . no C3 C4 1.530(5) . . no C4 C5 1.503(4) . . no C4 C9 1.514(5) . . no C5 C6 1.528(5) . . no C6 C7 1.527(5) . . no C6 C13 1.526(4) . . no C7 C8 1.514(4) . . no C8 C9 1.517(5) . . no C9 C10 1.336(5) . . no C10 C11 1.528(5) . . no C10 C14 1.497(5) . . no C11 C12 1.515(5) . . no C15 C16 1.505(5) . . no C2 H2A 0.9700 . . no C2 H2B 0.9700 . . no C3 H3 0.9800 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C6 H6 0.9800 . . no C7 H7 0.9800 . . no C8 H8A 0.9700 . . no C8 H8B 0.9700 . . no C11 H11A 0.9700 . . no C11 H11B 0.9700 . . no C12 H12 0.9800 . . no C13 H13A 0.9600 . . no C13 H13B 0.9600 . . no C13 H13C 0.9600 . . no C14 H14A 0.9600 . . no C14 H14B 0.9600 . . no C14 H14C 0.9600 . . no C16 H16A 0.9600 . . no C16 H16B 0.9600 . . no C16 H16C 0.9600 . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 O3 2.925(3) . 4_445 no O2 C13 3.356(5) . 4_445 no O3 C2 3.375(4) . 4_555 no O3 O2 2.925(3) . 4_455 no O5 C11 3.084(4) . . no O5 C1 2.958(4) . 1_655 no O5 C2 3.137(4) . 1_655 no O1 H13A 2.4600 . . no O1 H3A 2.8900 . 4_445 no O2 H16B 2.5500 . 3_445 no O2 H13C 2.5200 . 4_445 no O2 H3A 2.1300 . 4_445 no O3 H13C 2.6800 . . no O3 H2B 2.4600 . 4_555 no O4 H2A 2.6800 . . no O5 H2A 2.7500 . 1_655 no O5 H3 2.8200 . 1_655 no O5 H11B 2.5900 . . no O5 H12 2.4900 . . no C1 O5 2.958(4) . 1_455 no C2 O3 3.375(4) . 4_545 no C2 O5 3.137(4) . 1_455 no C11 O5 3.084(4) . . no C13 O2 3.356(5) . 4_455 no C1 H3A 2.9100 . 4_445 no C1 H4 2.9000 . . no C8 H14A 3.0100 . . no C8 H14B 3.0300 . . no C8 H13B 3.0200 . 1_655 no C9 H13B 2.8700 . 1_655 no C9 H12 3.0400 . . no C10 H3 3.0300 . . no C10 H13B 2.9200 . 1_655 no C13 H3A 2.7000 . . no C13 H8A 3.0800 . 1_455 no C14 H8B 2.6500 . . no C15 H11B 2.9000 . . no C16 H14B 2.7800 . 3_555 no H2A O4 2.6800 . . no H2A O5 2.7500 . 1_455 no H2B H4 2.5600 . . no H2B H12 2.5000 . . no H2B O3 2.4600 . 4_545 no H3 O5 2.8200 . 1_455 no H3 C10 3.0300 . . no H3 H5 2.3800 . . no H3 H11A 2.5300 . . no H3A C13 2.7000 . . no H3A H13C 2.2200 . . no H3A O1 2.8900 . 4_455 no H3A O2 2.1300 . 4_455 no H3A C1 2.9100 . 4_455 no H4 C1 2.9000 . . no H4 H2B 2.5600 . . no H4 H6 2.5000 . . no H4 H12 2.5100 . . no H5 H3 2.3800 . . no H5 H7 2.4800 . . no H5 H13B 2.5900 . . no H6 H4 2.5000 . . no H6 H14B 2.5900 . 4_545 no H7 H5 2.4800 . . no H7 H13B 2.5800 . . no H7 H14A 2.5800 . 1_455 no H8A C13 3.0800 . 1_655 no H8A H13B 2.4600 . 1_655 no H8B C14 2.6500 . . no H8B H14A 2.5700 . . no H8B H14B 2.4200 . . no H11A H3 2.5300 . . no H11A H11B 2.5800 . 3_455 no H11B O5 2.5900 . . no H11B C15 2.9000 . . no H11B H14C 2.2400 . . no H11B H11A 2.5800 . 3_555 no H12 O5 2.4900 . . no H12 C9 3.0400 . . no H12 H2B 2.5000 . . no H12 H4 2.5100 . . no H13A O1 2.4600 . . no H13B C8 3.0200 . 1_455 no H13B C9 2.8700 . 1_455 no H13B C10 2.9200 . 1_455 no H13B H5 2.5900 . . no H13B H7 2.5800 . . no H13B H8A 2.4600 . 1_455 no H13B H14A 2.6000 . 1_455 no H13C O3 2.6800 . . no H13C H3A 2.2200 . . no H13C O2 2.5200 . 4_455 no H14A C8 3.0100 . . no H14A H7 2.5800 . 1_655 no H14A H8B 2.5700 . . no H14A H13B 2.6000 . 1_655 no H14B C8 3.0300 . . no H14B H8B 2.4200 . . no H14B C16 2.7800 . 3_455 no H14B H16C 2.2200 . 3_455 no H14B H6 2.5900 . 4_555 no H14C H11B 2.2400 . . no H16B O2 2.5500 . 3_545 no H16C H14B 2.2200 . 3_555 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 O3 H3A O2 0.8200 2.1300 2.925(3) 163.00 4_455 yes C2 H2B O3 0.9700 2.4600 3.375(4) 156.00 4_545 yes C11 H11B O5 0.9700 2.5900 3.084(4) 112.00 . yes C13 H13A O1 0.9600 2.4600 2.810(5) 101.00 . yes C13 H13C O2 0.9600 2.5200 3.356(5) 145.00 4_455 yes C16 H16B O2 0.9600 2.5500 3.475(5) 161.00 3_545 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 C5 O1 C1 O2 -170.7(3) . . . . no C5 O1 C1 C2 12.4(4) . . . . no C1 O1 C5 C6 -157.3(3) . . . . no C1 O1 C5 C4 -33.4(4) . . . . no C15 O4 C12 C3 -161.3(3) . . . . no C12 O4 C15 C16 174.7(3) . . . . no C12 O4 C15 O5 -5.5(5) . . . . no C15 O4 C12 C11 78.2(3) . . . . no O2 C1 C2 C3 166.0(3) . . . . no O1 C1 C2 C3 -17.4(5) . . . . no C1 C2 C3 C4 42.3(4) . . . . no C1 C2 C3 C12 163.7(3) . . . . no C2 C3 C12 O4 54.9(3) . . . . no C2 C3 C4 C5 -62.6(3) . . . . no C2 C3 C12 C11 175.7(3) . . . . no C4 C3 C12 O4 176.0(3) . . . . no C12 C3 C4 C9 47.8(4) . . . . no C12 C3 C4 C5 172.6(3) . . . . no C2 C3 C4 C9 172.6(3) . . . . no C4 C3 C12 C11 -63.2(3) . . . . no C3 C4 C9 C8 169.0(3) . . . . no C5 C4 C9 C10 -140.9(3) . . . . no C3 C4 C9 C10 -18.2(4) . . . . no C9 C4 C5 C6 -55.3(4) . . . . no C3 C4 C5 C6 178.7(3) . . . . no C9 C4 C5 O1 -175.9(3) . . . . no C5 C4 C9 C8 46.2(4) . . . . no C3 C4 C5 O1 58.1(3) . . . . no O1 C5 C6 C7 -177.3(2) . . . . no C4 C5 C6 C7 59.8(3) . . . . no C4 C5 C6 C13 -174.9(3) . . . . no O1 C5 C6 C13 -52.0(4) . . . . no C5 C6 C7 O3 -175.6(2) . . . . no C13 C6 C7 C8 179.6(3) . . . . no C5 C6 C7 C8 -55.9(3) . . . . no C13 C6 C7 O3 59.9(3) . . . . no C6 C7 C8 C9 49.7(4) . . . . no O3 C7 C8 C9 172.8(3) . . . . no C7 C8 C9 C10 143.0(3) . . . . no C7 C8 C9 C4 -44.3(4) . . . . no C4 C9 C10 C11 3.0(5) . . . . no C4 C9 C10 C14 -174.8(3) . . . . no C8 C9 C10 C11 175.1(3) . . . . no C8 C9 C10 C14 -2.7(5) . . . . no C14 C10 C11 C12 159.8(3) . . . . no C9 C10 C11 C12 -18.2(4) . . . . no C10 C11 C12 O4 167.9(2) . . . . no C10 C11 C12 C3 48.6(3) . . . . no _journal_paper_doi 10.1039/c0ob00919a