# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1222 data_1 _publ_contact_author ; Mitsuhiro Yoshimatsu Faculty of Education Gifu University 1-1 Yanagido Gifu 501-1193 Japan ; _publ_contact_author_email yoshimae@cc.gifu-u.ac.jp _publ_contact_author_fax 001-81-582-93-2207 _publ_contact_author_phone 00-81-582-93-2251 _publ_contact_letter ? _publ_requested_coeditor_name ? _publ_requested_journal 'ChemComm' #=========================================================== # Manuscript text #=========================================================== loop_ _publ_author_name _publ_author_address 'Mitsuhiro, Yoshimatsu' ; Faculty of Education Gifu University 1-1 Yanagido Gifu 501-1193 Japan ; 'Satoshi Gotoh' ; Faculty of Education Gifu University 1-1 Yanagido Gifu 501-1193 Japan ; 'Genzoh Tanabe' ; Kinki University Faculty of Pharmaceutical Sciences 3-4-1 Kowakae Higashi-osaka Osaka 577-8502 Japan ; 'Osamu Muraoka' ; Kinki University Faculty of Pharmaceutical Sciences 3-4-1 Kowakae Higashi-osaka Osaka 577-8502 Japan ; #===================================================================== # TEXT #====================================================== _publ_section_title ;Compound name (1R*,5R*,6S*)-6-t-Butyl-1,4,7-tris(phenylthio)-2-oxabicyclo[3.3.0]octa-3,7-diene ; _publ_section_abstract ; The photo-reactions of the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal 1 and its 2,4- dinitrophenylhydrazone 5 gave the 2-oxa- or 2-azabicyclo[3.3.0]octa-3,7-dienes 2 and 9, respectively, via a photo-induced intramolecular tandem cyclization reaction. ; #========================================================= # EXPERIMENTAL #========================================================= _chemical_compound_source ; An acetonitrile solution (1400 ml) solution of (2E,4E,6E)-2,4,6- tris(phenylthio)nona-2,4,6-trienal 1 (1.80 g, 3.68 mmol) was irradiated by a 40W fluorecent daylight lamp for 3 days. The solvent was removed under reduced pressure. The residue was purified by preparative TLC on eluting with AcOEt-hexane (1:40) to afford (1R*,5R*,6S*)-6-t-butyl-1,4,7-tris(phenylthio)-2-oxabicyclo[3.3.0]octa- 3,7-diene (2) (0.98 g, 54%) as colorless prisms. ; _chemical_formula_sum 'C29 H28 O S3' _chemical_formula_moiety 'C29 H28 O S3' _chemical_formula_weight 488.72 _symmetry_cell_setting ' monoclinic ' _symmetry_space_group_name_H-M 'P2~1~/n ' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' _cell_length_a 9.007(2) _cell_length_b 26.879(6) _cell_length_c 10.945(2) _cell_angle_alpha 90.02(2) _cell_angle_beta 99.34(2) _cell_angle_gamma 89.99(2) _cell_volume 2614.7(9) _cell_formula_units_z 4 _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _diffrn_radiation_type 'CuIKa' _diffrn_radiation_wavelength 1.54178 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 90.0 _cell_measurement_theta_max -90.0 _exptl_absorpt_coefficient_mu 27.28 _cell_measurement_temperature 298 _exptl_crystal_description prism _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.38 _exptl_crystal_size_rad ? _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method 'IW-2Iq' _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.743 _exptl_absorpt_correction_T_max 1.000 _diffrn_reflns_number 4284 _reflns_number_total 4096 _reflns_number_observed 2720 _reflns_observed_criterion 'I>3.00IS(I)' _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 60.0720 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 26.13 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.056 _refine_ls_wR_factor_obs 0.070 _refine_ls_goodness_of_fit_obs 3.28 _refine_ls_number_reflns 2521 _refine_ls_number_parameters 298 _refine_ls_hydrogen_treatment 'noref' _refine_ls_weighting_scheme 'w = 4F~o~^2^/IS^2^(F~o~^2^)' _refine_ls_shift/esd_max 0.00 _refine_diff_density_max 0.26 _refine_diff_density_min -0.31 _refine_ls_extinction_method 'none' _refine_ls_extinction_coef ? _atom_type_scat_source ;International Tables for X-ray Crystallography Vol.IV ; _refine_ls_abs_structure_details ? _computing_data_collection ;MSC/AFC Diffractometer Control Software(Molecular Structure Corporation, 1988) ; _computing_cell_refinement ; MSC/AFC Diffractometer Control Software(Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN. TEXRAY Structure Analysis Package (Molecular Srtucture Corporation, 1985) ; _computing_structure_solution ;MITHRIL90 (Gilmore,1990) & DIRDIF (Beurskens, 1984) ; _computing_structure_refinement ; TEXSAN. TEXRAY Structure Analysis Package (Molecular Structure Corporation, 1985) ; _computing_molecular_graphics ;ORTEPII(Johnson, 1976) ; _computing_publication_material ? _publ_section_experimental ; H atoms were fixed at the calculated positions and included in the structure factor calculations with the exception of those involved in hyfrogen bonding which were located from difference Fourier map and refined isotropically. ; _publ_section_acknowledgements ? _publ_section_references ;Beurskens, P. T. (1984). Technical Report 1984, Crystallography lab. Toernooiveld, 6525 Ed Nijmegen, Netherlands. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Molecular Structure Corporation (1988). MSC/AFC Diffractometer Control System. MSC, 3200A Research Forest Drivew, The Woodlands TX 77381, USA. Molecular Structure Corporation (1985). TEXSAN. TEXRAY Structure Analysis Package. MSC, 3200A Research Forest Drivew, The Woodlands, TX 77381, USA. Gilmore, C. J. (1990). MITHRIL90. -an integrated direct methods computer program. ? University of Glasgrow, Scotland. ; _publ_section_figure_captions ; figure_captions?here ?For example; Fig. 1. ORTEPII(Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Ellipsoids for non-H atoms correspond to 40% probability. ; _publ_section_table_legends ; table_legends?Fig. 2 ORTEP Drawing of (1R*,5R*,6S*)-6-t-Butyl-1,4,7-tris (phenylthio)-2-oxabicyclo[3.3.0]octa-3,7-diene (2). B~eq~=(8Ip^2^/3)IS~i~IS~j~U~ij~a~i~^*^a~j~^*^a~i~.a~j~. Table 2. Selected bond length (I%A) and angles(I%). ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv S1 -0.0045(2) 0.20264(6) 1.3145(2) 0.0680 S2 0.1303(2) 0.06061(6) 0.9846(2) 0.0610 S3 -0.3521(2) 0.04628(7) 1.2650(2) 0.0691 O1 0.1591(5) 0.1199(2) 1.3151(4) 0.0585 C1 0.0043(7) 0.1379(2) 1.2706(5) 0.0504 C2 0.2060(7) 0.0958(2) 1.2193(6) 0.0559 C3 0.1076(7) 0.0963(2) 1.1151(6) 0.0491 C4 -0.0299(6) 0.1259(2) 1.1296(5) 0.0430 C5 -0.1785(6) 0.0955(2) 1.1073(5) 0.0469 C6 -0.2048(7) 0.0865(2) 1.2398(6) 0.0506 C7 -0.1081(7) 0.1088(2) 1.3263(6) 0.0533 C8 -0.3093(7) 0.1226(3) 1.0190(6) 0.0629 C9 -0.2498(9) 0.1387(3) 0.9009(7) 0.0836 C10 -0.4380(8) 0.0839(3) 0.9805(7) 0.0810 C11 -0.3682(9) 0.1681(3) 1.0808(8) 0.0960 C12 0.1612(6) 0.1063(2) 0.8728(6) 0.0525 C13 0.1243(9) 0.2313(2) 1.2308(7) 0.0644 C14 -0.3243(7) 0.0421(2) 1.4304(6) 0.0577 C15 0.2039(7) 0.1545(2) 0.9022(6) 0.0596 C16 0.1475(8) 0.0896(3) 0.7510(7) 0.0759 C17 0.276(1) 0.2280(3) 1.2724(8) 0.0886 C18 0.070(1) 0.2585(3) 1.1278(8) 0.0916 C19 -0.2092(8) 0.0131(3) 1.4915(7) 0.0664 C20 -0.4248(8) 0.0658(3) 1.4948(7) 0.0727 C21 0.178(1) 0.1217(4) 0.6604(7) 0.0965 C22 0.2342(9) 0.1850(3) 0.8094(8) 0.0800 C23 0.220(1) 0.1689(4) 0.6896(9) 0.0969 C24 0.171(2) 0.2842(4) 1.066(1) 0.1318 C25 0.377(1) 0.2532(4) 1.212(1) 0.1239 C26 0.321(2) 0.2812(5) 1.110(1) 0.1343 C27 -0.1919(9) 0.0079(3) 1.6181(7) 0.0737 C28 -0.405(1) 0.0590(3) 1.6227(8) 0.0881 C29 -0.290(1) 0.0302(3) 1.6819(7) 0.0843 H1 -0.0987 0.1050 1.4281 0.1129 H2 -0.0314 0.1596 1.0762 0.1129 H3 -0.1919 0.1115 0.8681 0.1129 H4 -0.1683 0.1653 0.9146 0.1129 H5 -0.3283 0.1490 0.8432 0.1129 H6 -0.2848 0.1947 1.0916 0.1129 H7 -0.4505 0.1874 1.0277 0.1129 H8 -0.4108 0.1558 1.1419 0.1129 H9 -0.5143 0.0983 0.9175 0.1129 H10 -0.3995 0.0477 0.9449 0.1129 H11 -0.4947 0.0747 1.0483 0.1129 H12 0.3235 0.0795 1.2436 0.1129 H13 -0.1480 0.0567 1.0750 0.1129 H14 0.3138 0.2074 1.3466 0.1085 H15 -0.0405 0.2599 1.0975 0.1143 H16 0.1352 0.3044 0.9915 0.1589 H17 0.4870 0.2506 1.2422 0.1481 H18 0.3931 0.2989 1.0687 0.1143 H19 -0.1402 -0.0038 1.4446 0.0806 H20 -0.5060 0.0863 1.4517 0.1563 H21 -0.1071 -0.0116 1.6625 0.0911 H22 -0.4739 0.0754 1.6702 0.1051 H23 -0.2790 0.0254 1.7719 0.1023 H24 0.2123 0.1666 0.9875 0.0741 H25 0.1158 0.0552 0.7308 0.0901 H26 0.1698 0.1103 0.5749 0.1141 H27 0.2675 0.2193 0.8295 0.0960 H28 0.2397 0.1920 0.6251 0.1023 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 S(1) C(1) 1.811(6) . . yes S(1) C(13) 1.768(7) . . yes S(2) C(3) 1.760(6) . . yes S(2) C(12) 1.787(6) . . yes S(3) C(6) 1.768(6) . . yes S(3) C(14) 1.789(6) . . yes O(1) C(1) 1.481(7) . . yes O(1) C(2) 1.356(7) . . yes C(1) C(4) 1.557(8) . . yes C(1) C(7) 1.486(8) . . yes C(2) C(3) 1.326(8) . . yes C(2) H(12) 1.1370 . . no C(3) C(4) 1.500(8) . . yes C(4) C(5) 1.553(8) . . yes C(4) H(2) 1.0795 . . no C(5) C(6) 1.527(8) . . yes C(5) C(8) 1.575(8) . . yes C(5) H(13) 1.1493 . . no C(6) C(7) 1.321(8) . . yes C(7) H(1) 1.1087 . . no C(8) C(9) 1.540(9) . . yes C(8) C(10) 1.564(10) . . yes C(8) C(11) 1.534(10) . . yes C(9) H(3) 0.9990 . . no C(9) H(4) 1.0168 . . no C(9) H(5) 0.9117 . . no C(10) H(9) 0.9721 . . no C(10) H(10) 1.1236 . . no C(10) H(11) 0.9975 . . no C(11) H(6) 1.0303 . . no C(11) H(7) 1.0089 . . no C(11) H(8) 0.8869 . . no C(12) C(15) 1.375(9) . . yes C(12) C(16) 1.393(9) . . yes C(13) C(17) 1.37(1) . . yes C(13) C(18) 1.37(1) . . yes C(14) C(19) 1.379(9) . . yes C(14) C(20) 1.390(9) . . yes C(15) C(22) 1.368(9) . . yes C(15) H(24) 0.9802 . . no C(16) C(21) 1.37(1) . . yes C(16) H(25) 0.9812 . . no C(17) C(25) 1.39(1) . . yes C(17) H(14) 0.9949 . . no C(18) C(24) 1.40(1) . . yes C(18) H(15) 0.9949 . . no C(19) C(27) 1.377(10) . . yes C(19) H(19) 0.9801 . . no C(20) C(28) 1.39(1) . . yes C(20) H(20) 0.9742 . . no C(21) C(23) 1.35(1) . . yes C(21) H(26) 0.9752 . . no C(22) C(23) 1.37(1) . . yes C(22) H(27) 0.9834 . . no C(23) H(28) 0.9777 . . no C(24) C(26) 1.37(2) . . yes C(24) H(16) 0.9872 . . no C(25) C(26) 1.37(2) . . yes C(25) H(17) 0.9948 . . no C(26) H(18) 0.9704 . . no C(27) C(29) 1.35(1) . . yes C(27) H(21) 0.9866 . . no C(28) C(29) 1.37(1) . . yes C(28) H(22) 0.9749 . . no C(29) H(23) 0.9820 . . no 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 C(1) S(1) C(13) 102.7(3) . . . yes C(3) S(2) C(12) 103.5(3) . . . yes C(6) S(3) C(14) 102.2(3) . . . yes C(1) O(1) C(2) 107.2(4) . . . yes S(1) C(1) O(1) 107.8(4) . . . yes S(1) C(1) C(4) 116.9(4) . . . yes S(1) C(1) C(7) 109.5(4) . . . yes O(1) C(1) C(4) 106.4(4) . . . yes O(1) C(1) C(7) 111.1(5) . . . yes C(4) C(1) C(7) 105.0(5) . . . yes O(1) C(2) C(3) 114.3(5) . . . yes O(1) C(2) H(12) 113.4888 . . . no C(3) C(2) H(12) 132.1700 . . . no S(2) C(3) C(2) 122.9(5) . . . yes S(2) C(3) C(4) 125.5(5) . . . yes C(2) C(3) C(4) 111.2(5) . . . yes C(1) C(4) C(3) 100.4(5) . . . yes C(1) C(4) C(5) 107.0(4) . . . yes C(1) C(4) H(2) 110.1932 . . . no C(3) C(4) C(5) 114.3(5) . . . yes C(3) C(4) H(2) 109.0038 . . . no C(5) C(4) H(2) 114.9634 . . . no C(4) C(5) C(6) 101.3(5) . . . yes C(4) C(5) C(8) 113.2(5) . . . yes C(4) C(5) H(13) 106.3533 . . . no C(6) C(5) C(8) 116.1(5) . . . yes C(6) C(5) H(13) 103.3045 . . . no C(8) C(5) H(13) 115.0202 . . . no S(3) C(6) C(5) 118.7(5) . . . yes S(3) C(6) C(7) 126.2(5) . . . yes C(5) C(6) C(7) 115.0(5) . . . yes C(1) C(7) C(6) 111.0(5) . . . yes C(1) C(7) H(1) 121.0795 . . . no C(6) C(7) H(1) 127.6823 . . . no C(5) C(8) C(9) 108.5(5) . . . yes C(5) C(8) C(10) 107.9(5) . . . yes C(5) C(8) C(11) 112.0(6) . . . yes C(9) C(8) C(10) 107.8(6) . . . yes C(9) C(8) C(11) 109.7(6) . . . yes C(10) C(8) C(11) 110.8(6) . . . yes C(8) C(9) H(3) 111.5725 . . . no C(8) C(9) H(4) 114.6076 . . . no C(8) C(9) H(5) 109.3398 . . . no H(3) C(9) H(4) 99.2255 . . . no H(3) C(9) H(5) 111.3548 . . . no H(4) C(9) H(5) 110.4533 . . . no C(8) C(10) H(9) 109.4530 . . . no C(8) C(10) H(10) 114.3029 . . . no C(8) C(10) H(11) 114.2892 . . . no H(9) C(10) H(10) 108.8611 . . . no H(9) C(10) H(11) 103.8275 . . . no H(10) C(10) H(11) 105.4747 . . . no C(8) C(11) H(6) 107.8823 . . . no C(8) C(11) H(7) 115.5430 . . . no C(8) C(11) H(8) 104.9964 . . . no H(6) C(11) H(7) 99.3367 . . . no H(6) C(11) H(8) 124.6686 . . . no H(7) C(11) H(8) 104.9475 . . . no S(2) C(12) C(15) 123.8(5) . . . yes S(2) C(12) C(16) 115.8(5) . . . yes C(15) C(12) C(16) 120.3(6) . . . yes S(1) C(13) C(17) 120.1(6) . . . yes S(1) C(13) C(18) 118.9(6) . . . yes C(17) C(13) C(18) 121.0(7) . . . yes S(3) C(14) C(19) 119.8(5) . . . yes S(3) C(14) C(20) 119.2(6) . . . yes C(19) C(14) C(20) 120.9(6) . . . yes C(12) C(15) C(22) 118.3(7) . . . yes C(12) C(15) H(24) 120.7708 . . . no C(22) C(15) H(24) 120.9211 . . . no C(12) C(16) C(21) 119.4(7) . . . yes C(12) C(16) H(25) 119.7123 . . . no C(21) C(16) H(25) 120.8622 . . . no C(13) C(17) C(25) 120.3(10) . . . yes C(13) C(17) H(14) 119.9111 . . . no C(25) C(17) H(14) 119.7997 . . . no C(13) C(18) C(24) 119.3(10) . . . yes C(13) C(18) H(15) 120.0843 . . . no C(24) C(18) H(15) 120.6336 . . . no C(14) C(19) C(27) 120.0(7) . . . yes C(14) C(19) H(19) 119.8988 . . . no C(27) C(19) H(19) 120.0963 . . . no C(14) C(20) C(28) 117.6(7) . . . yes C(14) C(20) H(20) 120.8973 . . . no C(28) C(20) H(20) 121.5481 . . . no C(16) C(21) C(23) 120.1(8) . . . yes C(16) C(21) H(26) 120.2188 . . . no C(23) C(21) H(26) 119.6990 . . . no C(15) C(22) C(23) 121.5(8) . . . yes C(15) C(22) H(27) 119.1455 . . . no C(23) C(22) H(27) 119.3601 . . . no C(21) C(23) C(22) 120.3(8) . . . yes C(21) C(23) H(28) 120.2701 . . . no C(22) C(23) H(28) 119.3890 . . . no C(18) C(24) C(26) 119(1) . . . yes C(18) C(24) H(16) 121.5171 . . . no C(26) C(24) H(16) 119.4491 . . . no C(17) C(25) C(26) 118(1) . . . yes C(17) C(25) H(17) 119.8941 . . . no C(26) C(25) H(17) 121.7329 . . . no C(24) C(26) C(25) 122(1) . . . yes C(24) C(26) H(18) 120.4661 . . . no C(25) C(26) H(18) 117.4953 . . . no C(19) C(27) C(29) 119.8(7) . . . yes C(19) C(27) H(21) 120.1528 . . . no C(29) C(27) H(21) 120.0329 . . . no C(20) C(28) C(29) 120.8(7) . . . yes C(20) C(28) H(22) 119.2361 . . . no C(29) C(28) H(22) 119.9782 . . . no C(27) C(29) C(28) 121.0(7) . . . yes C(27) C(29) H(23) 119.3851 . . . no C(28) C(29) H(23) 119.6364 . . . no 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 S1 0.086(1) 0.058(1) 0.069(1) -0.0109(9) 0.0381(10) -0.0132(8) S2 0.068(1) 0.0478(9) 0.074(1) 0.0015(8) 0.0330(9) -0.0039(8) S3 0.061(1) 0.088(1) 0.061(1) -0.0235(10) 0.0148(8) 0.0046(9) O1 0.053(3) 0.068(3) 0.051(3) -0.007(2) 0.001(2) 0.005(2) C1 0.054(4) 0.049(4) 0.050(4) -0.002(3) 0.015(3) 0.000(3) C2 0.049(4) 0.054(4) 0.065(4) -0.001(3) 0.010(3) 0.011(3) C3 0.051(4) 0.046(3) 0.055(4) 0.002(3) 0.021(3) 0.003(3) C4 0.043(3) 0.044(3) 0.044(3) 0.004(3) 0.013(3) 0.003(3) C5 0.041(3) 0.054(4) 0.047(3) 0.004(3) 0.011(3) 0.005(3) C6 0.045(4) 0.055(4) 0.054(4) -0.002(3) 0.017(3) 0.010(3) C7 0.054(4) 0.059(4) 0.049(4) -0.007(3) 0.014(3) 0.003(3) C8 0.055(4) 0.076(5) 0.056(4) 0.011(4) 0.004(3) 0.006(4) C9 0.076(5) 0.109(7) 0.061(5) -0.010(5) -0.004(4) 0.023(4) C10 0.049(4) 0.128(7) 0.064(5) -0.005(4) 0.002(4) 0.013(5) C11 0.085(6) 0.087(6) 0.113(7) 0.044(5) 0.005(5) 0.003(5) C12 0.040(3) 0.064(4) 0.056(4) 0.004(3) 0.017(3) 0.006(3) C13 0.082(5) 0.051(4) 0.067(5) -0.015(4) 0.034(4) -0.015(4) C14 0.059(4) 0.061(4) 0.056(4) -0.019(4) 0.019(3) 0.003(3) C15 0.057(4) 0.056(4) 0.068(4) -0.008(3) 0.018(3) 0.001(3) C16 0.076(5) 0.086(5) 0.068(5) -0.007(4) 0.019(4) -0.016(4) C17 0.098(7) 0.076(5) 0.097(6) -0.030(5) 0.034(5) -0.020(5) C18 0.112(7) 0.077(6) 0.090(6) -0.015(5) 0.028(5) 0.012(5) C19 0.073(5) 0.063(4) 0.068(5) -0.002(4) 0.024(4) 0.007(4) C20 0.067(5) 0.075(5) 0.079(5) -0.007(4) 0.021(4) -0.008(4) C21 0.099(7) 0.140(9) 0.053(5) -0.008(6) 0.020(5) 0.003(5) C22 0.076(5) 0.071(5) 0.095(6) -0.010(4) 0.021(5) 0.013(5) C23 0.091(7) 0.116(8) 0.088(7) -0.001(6) 0.028(5) 0.039(6) C24 0.22(1) 0.088(7) 0.101(8) -0.025(10) 0.051(10) -0.001(6) C25 0.108(8) 0.119(9) 0.16(1) -0.058(7) 0.067(8) -0.057(8) C26 0.21(2) 0.102(9) 0.112(10) -0.06(1) 0.10(1) -0.030(7) C27 0.085(6) 0.064(5) 0.075(5) -0.009(4) 0.019(4) 0.014(4) C28 0.104(7) 0.091(6) 0.079(6) -0.011(5) 0.045(5) -0.024(5) C29 0.114(7) 0.078(6) 0.064(5) -0.012(5) 0.024(5) 0.004(4) 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 S(1) C(1) O(1) C(2) -131.8(4) . . . . no S(1) C(1) C(4) C(3) 127.0(4) . . . . no S(1) C(1) C(4) C(5) -113.5(5) . . . . no S(1) C(1) C(7) C(6) 121.1(5) . . . . no S(1) C(13) C(17) C(25) -175.6(6) . . . . no S(1) C(13) C(18) C(24) 175.5(7) . . . . no S(2) C(3) C(2) O(1) -170.9(4) . . . . no S(2) C(3) C(4) C(1) 167.5(4) . . . . no S(2) C(3) C(4) C(5) 53.5(6) . . . . no S(2) C(12) C(15) C(22) 175.5(5) . . . . no S(2) C(12) C(16) C(21) -176.3(6) . . . . no S(3) C(6) C(5) C(4) -172.4(4) . . . . no S(3) C(6) C(5) C(8) 64.5(7) . . . . no S(3) C(6) C(7) C(1) 177.3(4) . . . . no S(3) C(14) C(19) C(27) -176.9(5) . . . . no S(3) C(14) C(20) C(28) 176.0(6) . . . . no O(1) C(1) S(1) C(13) 63.4(5) . . . . no O(1) C(1) C(4) C(3) 6.5(5) . . . . no O(1) C(1) C(4) C(5) 126.0(4) . . . . no O(1) C(1) C(7) C(6) -119.9(6) . . . . no O(1) C(2) C(3) C(4) 2.4(7) . . . . no C(1) S(1) C(13) C(18) 104.6(6) . . . . no C(1) O(1) C(2) C(3) 2.2(7) . . . . no C(1) C(4) C(3) C(2) -5.5(6) . . . . no C(1) C(4) C(5) C(6) -7.6(6) . . . . no C(1) C(4) C(5) C(8) 117.4(5) . . . . no C(1) C(7) C(6) C(5) 0.2(8) . . . . no C(2) O(1) C(1) C(4) -5.6(6) . . . . no C(2) O(1) C(1) C(7) 108.2(5) . . . . no C(2) C(3) S(2) C(12) -112.5(5) . . . . no C(2) C(3) C(4) C(5) -119.6(6) . . . . no C(3) S(2) C(12) C(15) 18.1(6) . . . . no C(3) S(2) C(12) C(16) -165.3(5) . . . . no C(3) C(4) C(1) C(7) -111.4(5) . . . . no C(3) C(4) C(5) C(6) 102.5(5) . . . . no C(3) C(4) C(5) C(8) -132.4(5) . . . . no C(4) C(1) S(1) C(13) -56.4(5) . . . . no C(4) C(1) C(7) C(6) -5.3(7) . . . . no C(4) C(3) S(2) C(12) 75.1(5) . . . . no C(4) C(5) C(6) C(7) 4.9(7) . . . . no C(4) C(5) C(8) C(9) 50.8(7) . . . . no C(4) C(5) C(8) C(10) 167.4(5) . . . . no C(4) C(5) C(8) C(11) -70.5(7) . . . . no C(5) C(4) C(1) C(7) 8.1(6) . . . . no C(5) C(6) S(3) C(14) 173.6(5) . . . . no C(6) S(3) C(14) C(19) -75.8(6) . . . . no C(6) C(5) C(8) C(9) 167.5(6) . . . . no C(6) C(5) C(8) C(10) -76.0(7) . . . . no C(6) C(5) C(8) C(11) 46.2(8) . . . . no C(7) C(1) S(1) C(13) -175.6(5) . . . . no C(7) C(6) S(3) C(14) -3.4(7) . . . . no C(7) C(6) C(5) C(8) -118.2(6) . . . . no C(12) C(15) C(22) C(23) 1(1) . . . . no C(12) C(16) C(21) C(23) 0(1) . . . . no C(13) C(17) C(25) C(26) 0(1) . . . . no C(13) C(18) C(24) C(26) 0(2) . . . . no C(14) C(19) C(27) C(29) 2(1) . . . . no C(14) C(20) C(28) C(29) 0(1) . . . . no C(15) C(12) C(16) C(21) 0(1) . . . . no C(15) C(22) C(23) C(21) -1(1) . . . . no C(16) C(12) C(15) C(22) -1(1) . . . . no C(16) C(21) C(23) C(22) 1(1) . . . . no C(17) C(13) C(18) C(24) -1(1) . . . . no C(17) C(25) C(26) C(24) -1(2) . . . . no C(18) C(13) C(17) C(25) 1(1) . . . . no C(18) C(24) C(26) C(25) 1(2) . . . . no C(19) C(14) C(20) C(28) 0(1) . . . . no C(19) C(27) C(29) C(28) -2(1) . . . . no C(20) C(14) C(19) C(27) -1(1) . . . . no C(20) C(28) C(29) C(27) 1(1) . . . . no