#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180282 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/68/7116895.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_7116895 loop_ _publ_author_name 'Hai-Bin Yang' 'Yu-Chao Yuan' 'Yin Wei' 'Min Shi' _publ_section_title ; Amine-catalyzed tunable reactions of allenoates with dithioesters: formal [4+2] and [2+2] cycloadditions for the synthesis of 2,3-dihydro-1,4-oxathiines and enantioenriched thietanes ; _journal_name_full Chem.Commun. _journal_page_first 6430 _journal_paper_doi 10.1039/C5cc01313E _journal_volume 51 _journal_year 2015 _chemical_formula_sum 'C18 H16 O3 S3' _chemical_formula_weight 376.49 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2014-03-19 deposited with the CCDC. 2015-03-05 downloaded from the CCDC. ; _cell_angle_alpha 85.804(4) _cell_angle_beta 82.143(3) _cell_angle_gamma 84.097(4) _cell_formula_units_Z 2 _cell_length_a 4.5264(7) _cell_length_b 13.238(2) _cell_length_c 14.614(2) _cell_measurement_reflns_used 1441 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 51.731 _cell_measurement_theta_min 6.199 _cell_volume 861.3(2) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_unetI/netI 0.0445 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5281 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.997 _diffrn_reflns_theta_min 2.031 _exptl_absorpt_coefficient_mu 0.444 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.452 _exptl_crystal_description prismatic _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.211 _exptl_crystal_size_mid 0.143 _exptl_crystal_size_min 0.102 _refine_diff_density_max 0.429 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.060 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3392 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0495 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.1852P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1327 _refine_ls_wR_factor_ref 0.1431 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2706 _reflns_number_total 3392 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5cc01313e2.cif _cod_data_source_block cd21482 _cod_database_code 7116895 #BEGIN Tags that were not found in dictionaries: _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd21482 in P-1 CELL 0.71073 4.5264 13.2385 14.6137 85.804 82.143 84.097 ZERR 2.00 0.0007 0.0021 0.0023 0.004 0.003 0.004 LATT 1 SFAC C H O S UNIT 36 32 6 6 OMIT 0 1 0 OMIT 3 2 1 OMIT 2 1 1 OMIT 0 1 3 OMIT -3.00 52.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB C18 S2_$1 EQIV $1 x+1, y, z HTAB C7 O2 conf htab mpla s1 c1 > c4 mpla c12 > c17 wpdb -1 WGHT 0.078900 0.185200 FVAR 0.27117 MOLE 1 S1 4 0.705293 0.436680 0.392088 11.00000 0.06396 0.04040 = 0.05367 -0.01081 -0.00759 -0.01154 S2 4 0.139753 0.121990 0.463607 11.00000 0.05593 0.04049 = 0.03784 -0.00439 -0.00051 -0.01227 S3 4 0.263816 0.317364 0.528619 11.00000 0.06501 0.03748 = 0.03910 -0.01129 -0.00340 -0.00030 O1 3 0.453576 0.201667 0.278361 11.00000 0.05936 0.03473 = 0.03394 -0.00700 -0.00541 -0.01268 O2 3 0.063895 -0.079395 0.269076 11.00000 0.09563 0.05304 = 0.04069 0.00004 -0.01261 -0.03369 O3 3 0.053235 -0.024840 0.120374 11.00000 0.06004 0.03841 = 0.04030 -0.00528 -0.01612 -0.01160 C1 1 0.946288 0.488470 0.305991 11.00000 0.04940 0.03492 = 0.06431 -0.00735 -0.00736 -0.00809 AFIX 43 H1 2 1.039234 0.546766 0.311621 11.00000 -1.20000 AFIX 0 C2 1 0.987951 0.436778 0.229648 11.00000 0.05048 0.04640 = 0.05437 0.00077 0.00010 -0.00743 AFIX 43 H2 2 1.115140 0.455716 0.177087 11.00000 -1.20000 AFIX 0 C3 1 0.820822 0.349467 0.234963 11.00000 0.03800 0.02844 = 0.05128 -0.00016 -0.00203 -0.00907 AFIX 43 H3 2 0.820969 0.306243 0.187570 11.00000 -1.20000 AFIX 0 C4 1 0.655050 0.340059 0.324717 11.00000 0.03984 0.02919 = 0.03903 -0.00542 -0.01118 -0.00043 C5 1 0.466858 0.257446 0.354806 11.00000 0.04245 0.02707 = 0.03419 -0.00572 -0.01038 -0.00057 C6 1 0.316903 0.234821 0.438680 11.00000 0.04546 0.03175 = 0.03603 -0.00562 -0.00756 -0.00224 C7 1 0.366747 0.049575 0.375871 11.00000 0.05272 0.03247 = 0.03719 -0.00567 -0.01251 0.00021 AFIX 23 H7A 2 0.573067 0.039662 0.388398 11.00000 -1.20000 H7B 2 0.293769 -0.016586 0.374412 11.00000 -1.20000 AFIX 0 C8 1 0.346019 0.108547 0.286136 11.00000 0.04008 0.02959 = 0.03747 -0.00534 -0.00354 -0.00294 C9 1 0.240955 0.080642 0.211909 11.00000 0.05252 0.03437 = 0.03228 -0.00281 -0.00581 -0.00640 AFIX 43 H9 2 0.247941 0.125621 0.159871 11.00000 -1.20000 AFIX 0 C10 1 0.115420 -0.015906 0.206725 11.00000 0.04737 0.03819 = 0.03506 -0.00730 -0.00546 -0.00700 C11 1 -0.080282 -0.116580 0.104720 11.00000 0.05004 0.04661 = 0.05328 -0.01118 -0.01939 -0.01148 AFIX 23 H11A 2 -0.197718 -0.102719 0.053679 11.00000 -1.20000 H11B 2 -0.214469 -0.135490 0.159473 11.00000 -1.20000 AFIX 0 C12 1 0.151377 -0.203189 0.083245 11.00000 0.04288 0.03995 = 0.04299 -0.00698 -0.01258 -0.01477 C13 1 0.229703 -0.275063 0.152776 11.00000 0.05697 0.05088 = 0.04392 -0.00101 -0.00691 -0.01336 AFIX 43 H13 2 0.136151 -0.269334 0.213165 11.00000 -1.20000 AFIX 0 C14 1 0.446674 -0.355037 0.132110 11.00000 0.06615 0.04495 = 0.06924 0.00615 -0.01894 -0.01098 AFIX 43 H14 2 0.499324 -0.402435 0.178686 11.00000 -1.20000 AFIX 0 C15 1 0.583536 -0.364091 0.042787 11.00000 0.06111 0.05066 = 0.08359 -0.01606 -0.01316 -0.00131 AFIX 43 H15 2 0.727880 -0.417930 0.028962 11.00000 -1.20000 AFIX 0 C16 1 0.506992 -0.293033 -0.027028 11.00000 0.07081 0.06462 = 0.05464 -0.01541 0.00094 -0.00545 AFIX 43 H16 2 0.599790 -0.299226 -0.087449 11.00000 -1.20000 AFIX 0 C17 1 0.292754 -0.213354 -0.006161 11.00000 0.05963 0.05467 = 0.04536 -0.00387 -0.01360 -0.00908 AFIX 43 H17 2 0.242570 -0.165749 -0.052881 11.00000 -1.20000 AFIX 0 C18 1 0.449872 0.245809 0.617259 11.00000 0.06109 0.06379 = 0.04018 -0.01128 -0.00758 -0.00428 AFIX 137 H18A 2 0.360413 0.183149 0.633273 11.00000 -1.50000 H18B 2 0.430191 0.284785 0.670997 11.00000 -1.50000 H18C 2 0.658254 0.231324 0.594788 11.00000 -1.50000 AFIX 0 HKLF 4 REM cd21482 in P-1 REM R1 = 0.0495 for 2706 Fo > 4sig(Fo) and 0.0625 for all 3392 data REM 218 parameters refined using 0 restraints END WGHT 0.0781 0.2113 REM Instructions for potential hydrogen bonds HTAB C7 O2 HTAB C18 S2_$1 REM Highest difference peak 0.429, deepest hole -0.329, 1-sigma level 0.060 Q1 1 0.8521 0.3208 0.2211 11.00000 0.05 0.43 Q2 1 0.7922 0.3426 0.2059 11.00000 0.05 0.43 Q3 1 0.7173 0.3432 0.2582 11.00000 0.05 0.43 Q4 1 0.8523 0.3780 0.2270 11.00000 0.05 0.37 Q5 1 0.2822 0.2755 0.4778 11.00000 0.05 0.31 Q6 1 0.4464 0.3253 0.5185 11.00000 0.05 0.30 Q7 1 0.2378 0.1813 0.4535 11.00000 0.05 0.28 Q8 1 0.8969 0.4528 0.3481 11.00000 0.05 0.26 Q9 1 0.2458 -0.2212 0.1153 11.00000 0.05 0.25 Q10 1 0.4904 0.2324 0.4072 11.00000 0.05 0.25 Q11 1 1.0444 0.4427 0.2829 11.00000 0.05 0.24 Q12 1 0.6000 0.3033 0.3360 11.00000 0.05 0.24 Q13 1 0.2848 0.2510 0.3995 11.00000 0.05 0.24 Q14 1 0.1919 0.3766 0.5385 11.00000 0.05 0.24 Q15 1 0.5355 0.3232 0.3293 11.00000 0.05 0.23 Q16 1 0.3268 -0.3144 0.1355 11.00000 0.05 0.23 Q17 1 0.2179 0.1026 0.2620 11.00000 0.05 0.23 Q18 1 0.6007 0.3813 0.3629 11.00000 0.05 0.22 Q19 1 0.0294 0.0742 0.5073 11.00000 0.05 0.21 Q20 1 0.4928 -0.3474 0.0049 11.00000 0.05 0.21 ; _shelx_res_checksum 7506 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7053(2) 0.43668(6) 0.39209(6) 0.0518(2) Uani 1 1 d . . . . . S2 S 0.13975(18) 0.12199(6) 0.46361(5) 0.0446(2) Uani 1 1 d . . . . . S3 S 0.26382(19) 0.31736(6) 0.52862(5) 0.0474(2) Uani 1 1 d . . . . . O1 O 0.4536(5) 0.20167(14) 0.27836(12) 0.0419(5) Uani 1 1 d . . . . . O2 O 0.0639(6) -0.07940(17) 0.26908(14) 0.0610(6) Uani 1 1 d . . . . . O3 O 0.0532(5) -0.02484(14) 0.12037(13) 0.0447(5) Uani 1 1 d . . . . . C1 C 0.9463(7) 0.4885(2) 0.3060(2) 0.0490(7) Uani 1 1 d . . . . . H1 H 1.0392 0.5468 0.3116 0.059 Uiso 1 1 calc R U . . . C2 C 0.9880(7) 0.4368(2) 0.2296(2) 0.0510(7) Uani 1 1 d . . . . . H2 H 1.1151 0.4557 0.1771 0.061 Uiso 1 1 calc R U . . . C3 C 0.8208(6) 0.3495(2) 0.23496(19) 0.0393(6) Uani 1 1 d . . . . . H3 H 0.8210 0.3062 0.1876 0.047 Uiso 1 1 calc R U . . . C4 C 0.6551(6) 0.34006(19) 0.32472(18) 0.0355(6) Uani 1 1 d . . . . . C5 C 0.4669(6) 0.25745(19) 0.35481(17) 0.0341(6) Uani 1 1 d . . . . . C6 C 0.3169(6) 0.2348(2) 0.43868(18) 0.0375(6) Uani 1 1 d . . . . . C7 C 0.3667(7) 0.0496(2) 0.37587(17) 0.0403(6) Uani 1 1 d . . . . . H7A H 0.5731 0.0397 0.3884 0.048 Uiso 1 1 calc R U . . . H7B H 0.2938 -0.0166 0.3744 0.048 Uiso 1 1 calc R U . . . C8 C 0.3460(6) 0.1085(2) 0.28614(18) 0.0357(6) Uani 1 1 d . . . . . C9 C 0.2410(6) 0.0806(2) 0.21191(18) 0.0395(6) Uani 1 1 d . . . . . H9 H 0.2479 0.1256 0.1599 0.047 Uiso 1 1 calc R U . . . C10 C 0.1154(6) -0.0159(2) 0.20673(18) 0.0397(6) Uani 1 1 d . . . . . C11 C -0.0803(7) -0.1166(2) 0.1047(2) 0.0479(7) Uani 1 1 d . . . . . H11A H -0.1977 -0.1027 0.0537 0.057 Uiso 1 1 calc R U . . . H11B H -0.2145 -0.1355 0.1595 0.057 Uiso 1 1 calc R U . . . C12 C 0.1514(6) -0.2032(2) 0.08324(19) 0.0403(6) Uani 1 1 d . . . . . C13 C 0.2297(7) -0.2751(2) 0.1528(2) 0.0501(7) Uani 1 1 d . . . . . H13 H 0.1362 -0.2693 0.2132 0.060 Uiso 1 1 calc R U . . . C14 C 0.4467(8) -0.3550(3) 0.1321(3) 0.0592(9) Uani 1 1 d . . . . . H14 H 0.4993 -0.4024 0.1787 0.071 Uiso 1 1 calc R U . . . C15 C 0.5835(8) -0.3641(3) 0.0428(3) 0.0645(9) Uani 1 1 d . . . . . H15 H 0.7279 -0.4179 0.0290 0.077 Uiso 1 1 calc R U . . . C16 C 0.5070(9) -0.2930(3) -0.0270(2) 0.0637(9) Uani 1 1 d . . . . . H16 H 0.5998 -0.2992 -0.0874 0.076 Uiso 1 1 calc R U . . . C17 C 0.2928(7) -0.2134(2) -0.0062(2) 0.0523(8) Uani 1 1 d . . . . . H17 H 0.2426 -0.1657 -0.0529 0.063 Uiso 1 1 calc R U . . . C18 C 0.4499(8) 0.2458(3) 0.6173(2) 0.0546(8) Uani 1 1 d . . . . . H18A H 0.3604 0.1831 0.6333 0.082 Uiso 1 1 calc R U . . . H18B H 0.4302 0.2848 0.6710 0.082 Uiso 1 1 calc R U . . . H18C H 0.6583 0.2313 0.5948 0.082 Uiso 1 1 calc R U . . . 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 S1 0.0640(5) 0.0404(4) 0.0537(5) -0.0108(3) -0.0076(4) -0.0115(4) S2 0.0559(5) 0.0405(4) 0.0378(4) -0.0044(3) -0.0005(3) -0.0123(3) S3 0.0650(5) 0.0375(4) 0.0391(4) -0.0113(3) -0.0034(3) -0.0003(3) O1 0.0594(12) 0.0347(10) 0.0339(10) -0.0070(8) -0.0054(9) -0.0127(9) O2 0.0956(18) 0.0530(13) 0.0407(11) 0.0000(10) -0.0126(12) -0.0337(13) O3 0.0600(13) 0.0384(11) 0.0403(10) -0.0053(8) -0.0161(9) -0.0116(9) C1 0.0494(17) 0.0349(15) 0.0643(19) -0.0074(14) -0.0074(15) -0.0081(13) C2 0.0505(18) 0.0464(18) 0.0544(18) 0.0008(14) 0.0001(14) -0.0074(14) C3 0.0380(14) 0.0284(13) 0.0513(16) -0.0002(12) -0.0020(12) -0.0091(11) C4 0.0398(14) 0.0292(13) 0.0390(14) -0.0054(11) -0.0112(11) -0.0004(11) C5 0.0424(14) 0.0271(13) 0.0342(13) -0.0057(10) -0.0104(11) -0.0006(11) C6 0.0455(15) 0.0318(14) 0.0360(13) -0.0056(11) -0.0076(12) -0.0022(11) C7 0.0527(17) 0.0325(14) 0.0372(14) -0.0057(11) -0.0125(12) 0.0002(12) C8 0.0401(14) 0.0296(13) 0.0375(14) -0.0053(11) -0.0035(11) -0.0029(11) C9 0.0525(16) 0.0344(14) 0.0323(13) -0.0028(11) -0.0058(12) -0.0064(12) C10 0.0474(16) 0.0382(15) 0.0351(14) -0.0073(12) -0.0055(12) -0.0070(12) C11 0.0500(17) 0.0466(17) 0.0533(17) -0.0112(14) -0.0194(14) -0.0115(14) C12 0.0429(15) 0.0400(15) 0.0430(15) -0.0070(12) -0.0126(12) -0.0148(12) C13 0.0570(18) 0.0509(18) 0.0439(16) -0.0010(14) -0.0069(14) -0.0134(15) C14 0.066(2) 0.0450(18) 0.069(2) 0.0062(16) -0.0189(18) -0.0110(16) C15 0.061(2) 0.051(2) 0.084(3) -0.0161(19) -0.0132(19) -0.0013(16) C16 0.071(2) 0.065(2) 0.0546(19) -0.0154(17) 0.0009(17) -0.0055(19) C17 0.060(2) 0.0547(19) 0.0454(17) -0.0039(14) -0.0136(15) -0.0091(16) C18 0.061(2) 0.064(2) 0.0402(16) -0.0113(15) -0.0076(14) -0.0043(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 S1 C4 91.67(14) . . C6 S2 C7 96.69(13) . . C6 S3 C18 102.95(14) . . C8 O1 C5 122.6(2) . . C10 O3 C11 116.4(2) . . C2 C1 S1 113.0(2) . . C2 C1 H1 123.5 . . S1 C1 H1 123.5 . . C1 C2 C3 114.7(3) . . C1 C2 H2 122.6 . . C3 C2 H2 122.6 . . C4 C3 C2 108.7(3) . . C4 C3 H3 125.6 . . C2 C3 H3 125.6 . . C3 C4 C5 123.3(2) . . C3 C4 S1 111.9(2) . . C5 C4 S1 124.8(2) . . C6 C5 O1 122.2(2) . . C6 C5 C4 129.7(2) . . O1 C5 C4 108.0(2) . . C5 C6 S3 123.1(2) . . C5 C6 S2 122.1(2) . . S3 C6 S2 114.72(16) . . C8 C7 S2 106.96(18) . . C8 C7 H7A 110.3 . . S2 C7 H7A 110.3 . . C8 C7 H7B 110.3 . . S2 C7 H7B 110.3 . . H7A C7 H7B 108.6 . . C9 C8 O1 116.2(2) . . C9 C8 C7 127.9(2) . . O1 C8 C7 115.8(2) . . C8 C9 C10 124.4(2) . . C8 C9 H9 117.8 . . C10 C9 H9 117.8 . . O2 C10 O3 122.9(2) . . O2 C10 C9 127.2(2) . . O3 C10 C9 109.9(2) . . O3 C11 C12 111.9(2) . . O3 C11 H11A 109.2 . . C12 C11 H11A 109.2 . . O3 C11 H11B 109.2 . . C12 C11 H11B 109.2 . . H11A C11 H11B 107.9 . . C17 C12 C13 118.9(3) . . C17 C12 C11 120.3(3) . . C13 C12 C11 120.8(3) . . C14 C13 C12 120.3(3) . . C14 C13 H13 119.9 . . C12 C13 H13 119.9 . . C15 C14 C13 120.0(3) . . C15 C14 H14 120.0 . . C13 C14 H14 120.0 . . C14 C15 C16 120.3(3) . . C14 C15 H15 119.9 . . C16 C15 H15 119.9 . . C17 C16 C15 119.6(3) . . C17 C16 H16 120.2 . . C15 C16 H16 120.2 . . C16 C17 C12 121.0(3) . . C16 C17 H17 119.5 . . C12 C17 H17 119.5 . . S3 C18 H18A 109.5 . . S3 C18 H18B 109.5 . . H18A C18 H18B 109.5 . . S3 C18 H18C 109.5 . . H18A C18 H18C 109.5 . . H18B C18 H18C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.702(3) . S1 C4 1.721(3) . S2 C6 1.759(3) . S2 C7 1.799(3) . S3 C6 1.746(3) . S3 C18 1.800(3) . O1 C8 1.363(3) . O1 C5 1.395(3) . O2 C10 1.209(3) . O3 C10 1.346(3) . O3 C11 1.457(3) . C1 C2 1.333(4) . C1 H1 0.9300 . C2 C3 1.437(4) . C2 H2 0.9300 . C3 C4 1.423(4) . C3 H3 0.9300 . C4 C5 1.461(4) . C5 C6 1.347(4) . C7 C8 1.485(3) . C7 H7A 0.9700 . C7 H7B 0.9700 . C8 C9 1.332(4) . C9 C10 1.462(4) . C9 H9 0.9300 . C11 C12 1.493(4) . C11 H11A 0.9700 . C11 H11B 0.9700 . C12 C17 1.384(4) . C12 C13 1.397(4) . C13 C14 1.389(5) . C13 H13 0.9300 . C14 C15 1.374(5) . C14 H14 0.9300 . C15 C16 1.391(5) . C15 H15 0.9300 . C16 C17 1.379(5) . C16 H16 0.9300 . C17 H17 0.9300 . C18 H18A 0.9600 . C18 H18B 0.9600 . C18 H18C 0.9600 . 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 C18 H18C S2 0.96 3.02 3.879(3) 149.3 1_655 C7 H7B O2 0.97 2.22 2.947(3) 130.4 . 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 C4 S1 C1 C2 0.3(2) . . . . S1 C1 C2 C3 0.6(4) . . . . C1 C2 C3 C4 -1.5(4) . . . . C2 C3 C4 C5 -178.1(2) . . . . C2 C3 C4 S1 1.7(3) . . . . C1 S1 C4 C3 -1.2(2) . . . . C1 S1 C4 C5 178.6(2) . . . . C8 O1 C5 C6 -14.9(4) . . . . C8 O1 C5 C4 166.8(2) . . . . C3 C4 C5 C6 174.5(3) . . . . S1 C4 C5 C6 -5.3(4) . . . . C3 C4 C5 O1 -7.4(3) . . . . S1 C4 C5 O1 172.88(17) . . . . O1 C5 C6 S3 -165.99(18) . . . . C4 C5 C6 S3 11.9(4) . . . . O1 C5 C6 S2 10.2(4) . . . . C4 C5 C6 S2 -171.9(2) . . . . C18 S3 C6 C5 -118.7(3) . . . . C18 S3 C6 S2 64.87(19) . . . . C7 S2 C6 C5 24.0(2) . . . . C7 S2 C6 S3 -159.57(15) . . . . C6 S2 C7 C8 -55.6(2) . . . . C5 O1 C8 C9 155.7(2) . . . . C5 O1 C8 C7 -25.6(3) . . . . S2 C7 C8 C9 -119.0(3) . . . . S2 C7 C8 O1 62.5(3) . . . . O1 C8 C9 C10 -179.7(3) . . . . C7 C8 C9 C10 1.8(5) . . . . C11 O3 C10 O2 -0.3(4) . . . . C11 O3 C10 C9 -178.7(2) . . . . C8 C9 C10 O2 7.0(5) . . . . C8 C9 C10 O3 -174.8(3) . . . . C10 O3 C11 C12 -85.3(3) . . . . O3 C11 C12 C17 -84.0(3) . . . . O3 C11 C12 C13 95.9(3) . . . . C17 C12 C13 C14 0.2(4) . . . . C11 C12 C13 C14 -179.7(3) . . . . C12 C13 C14 C15 -0.5(5) . . . . C13 C14 C15 C16 0.4(5) . . . . C14 C15 C16 C17 0.0(5) . . . . C15 C16 C17 C12 -0.3(5) . . . . C13 C12 C17 C16 0.2(4) . . . . C11 C12 C17 C16 -179.9(3) . . . .