# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_address _publ_author_footnote ; ? # Address for author 1 ; ; ? #footnote for author 1 ; ; ? # Address 2 ; ; ? # footnote 2 ; _publ_contact_author_name 'Jonathan Burton' _publ_contact_author_email JONATHAN.BURTON@CHEM.OX.AC.UK _publ_section_title ; Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula ; _publ_contact_author_address ; University Chemical Laboratory Univeristy of Cambridge Cambridge CB2 1EW ; _publ_contact_author_fax '01223 336 362' _publ_contact_author_phone '01223 336 317' # cam172 in P2(1) #**************************************************************************** # The contents of this file between this point and the next ***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD# _publ_author_name 'Jonathan Burton' # Attachment 'cam172.cif' data_cam174S_cif _database_code_depnum_ccdc_archive 'CCDC 698760' _audit_creation_date 03-20-11 _audit_creation_method CRYSTALS_ver_12-03-99 #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 5.5615(17) _cell_angle_alpha 90 _cell_length_b 27.699(8) _cell_angle_beta 105.644(6) _cell_length_c 10.094(3) _cell_angle_gamma 90 _cell_volume 1497.4(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C15 H20 O5 S1 ' _chemical_formula_moiety ' C15 H20 O5 S1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 312.38 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' white ' _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_max 0.03 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 664.000 _exptl_absorpt_coefficient_mu 0.235 _diffrn_measurement_device_type ; Bruker AXS SMART 1K CCD diffractometer ; _diffrn_radiation_monochromator 'silicon 111' _computing_data_collection ; SMART (Siemens, 1993) ; _computing_data_reduction ; Bruker SAINT version 6.36a (Bruker, 2002) ; _computing_cell_refinement ; Bruker SAINT version 6.36a (Bruker, 2002) ; _computing_structure_solution ; SHELXS 86 (Sheldrick, 1986) ; _diffrn_measurement_method 'thin slice \w-scans' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; SADABS ; _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 293 _diffrn_reflns_number 10048 _reflns_number_total 6771 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 10014 # Number of reflections without Friedels Law is 6771 # Theoretical number of reflections is about 3746 _diffrn_reflns_theta_min 2.095 _diffrn_reflns_theta_max 28.409 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.841 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -36 _reflns_limit_k_max 36 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _refine_diff_density_min -0.68 _refine_diff_density_max 0.77 _refine_ls_number_reflns 4429 _refine_ls_number_restraints 1 _refine_ls_number_parameters 379 #_refine_ls_R_factor_ref 0.0464 _refine_ls_wR_factor_ref 0.0493 _refine_ls_goodness_of_fit_ref 1.1154 #_reflns_number_all 6755 _refine_ls_R_factor_all 0.0772 _refine_ls_wR_factor_all 0.0728 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 4429 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_gt 0.0493 _refine_ls_shift/su_max 0.002658 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 A~i~ are: 0.338 0.262 0.184 ; _refine_ls_abs_structure_Flack -0.008(80) _refine_ls_abs_structure_details 'Flack, 3243 Friedel-pairs' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; A New High Flux Chemical and Materials Crystallography Station at the SRS Daresbury: Part 1 Design, Commissioning and Test Results Cernik R.J., Clegg W., Catlow C.R.A., Bushnell-Wye G., Flaherty J.V., Greaves G.N., Hamichi M., Burrows I., Taylor D.J., Teat S.J. J. Synchrotron Rad.,(1997), 4 , 279-286 . Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags _atom_site_attached_hydrogens C1 C 0.8449(7) 0.25645(14) 0.3192(4) 0.0309 1.0000 Uani . . C2 C 0.8479(8) 0.30853(13) 0.3679(4) 0.0331 1.0000 Uani . . C3 C 0.6574(8) 0.31593(13) 0.4513(4) 0.0332 1.0000 Uani . . C4 C 0.6869(7) 0.27835(13) 0.5641(4) 0.0259 1.0000 Uani . . C5 C 0.7008(7) 0.22788(13) 0.5071(4) 0.0263 1.0000 Uani . . C6 C 0.7743(8) 0.19121(13) 0.6222(4) 0.0321 1.0000 Uani . . C7 C 1.0191(7) 0.20589(13) 0.7215(4) 0.0317 1.0000 Uani . . C8 C 1.0156(6) 0.25730(14) 0.7721(4) 0.0259 1.0000 Uani . . C9 C 0.5783(8) 0.20036(14) 0.1746(4) 0.0356 1.0000 Uani . . C10 C 0.9218(7) 0.31773(13) 0.9823(4) 0.0254 1.0000 Uani . . C11 C 0.7319(7) 0.35171(14) 0.9552(4) 0.0307 1.0000 Uani . . C12 C 0.7797(8) 0.39678(14) 1.0153(4) 0.0369 1.0000 Uani . . C13 C 1.0126(8) 0.40717(14) 1.1034(4) 0.0353 1.0000 Uani . . C14 C 1.2013(8) 0.37263(15) 1.1291(4) 0.0350 1.0000 Uani . . C15 C 1.1569(7) 0.32752(14) 1.0697(4) 0.0305 1.0000 Uani . . C16 C 0.1291(7) 0.05396(13) 0.5701(4) 0.0285 1.0000 Uani . . C17 C 0.1645(8) 0.00171(14) 0.6123(4) 0.0346 1.0000 Uani . . C18 C 0.4365(8) -0.00721(14) 0.6936(4) 0.0327 1.0000 Uani . . C19 C 0.5198(7) 0.02740(13) 0.8127(4) 0.0247 1.0000 Uani . . C20 C 0.4601(6) 0.07944(12) 0.7641(4) 0.0237 1.0000 Uani . . C21 C 0.5003(7) 0.11346(12) 0.8846(4) 0.0249 1.0000 Uani . . C22 C 0.3405(7) 0.09712(13) 0.9771(4) 0.0271 1.0000 Uani . . C23 C 0.3951(6) 0.04525(14) 1.0227(3) 0.0243 1.0000 Uani . . C24 C 0.2311(8) 0.11132(14) 0.4209(4) 0.0348 1.0000 Uani . . C25 C 0.6872(6) -0.01511(12) 1.2338(4) 0.0228 1.0000 Uani . . C26 C 0.8476(7) -0.05052(13) 1.2066(4) 0.0274 1.0000 Uani . . C27 C 0.8535(8) -0.09550(13) 1.2686(4) 0.0339 1.0000 Uani . . C28 C 0.7045(8) -0.10392(13) 1.3547(4) 0.0338 1.0000 Uani . . C29 C 0.5475(8) -0.06881(14) 1.3818(4) 0.0339 1.0000 Uani . . C30 C 0.5401(7) -0.02349(13) 1.3211(4) 0.0268 1.0000 Uani . . S1 S 0.86032(17) 0.25928(4) 0.9097(1) 0.0268 1.0000 Uani . . S2 S 0.68543(15) 0.04272(4) 1.15998(9) 0.0228 1.0000 Uani . . O1 O 0.6133(5) 0.24926(9) 0.2230(3) 0.0346 1.0000 Uani . . O2 O 0.8835(5) 0.22453(9) 0.4319(3) 0.0291 1.0000 Uani . . O3 O 0.9128(5) 0.29147(8) 0.6690(3) 0.0267 1.0000 Uani . . O4 O 0.5931(4) 0.25446(11) 0.8528(3) 0.0359 1.0000 Uani . . O5 O 0.9905(5) 0.2252(1) 1.0115(3) 0.0352 1.0000 Uani . . O6 O 0.2618(5) 0.06333(9) 0.4737(3) 0.0330 1.0000 Uani . . O7 O 0.2019(4) 0.08496(9) 0.6866(2) 0.0263 1.0000 Uani . . O8 O 0.3963(5) 0.01264(8) 0.9159(3) 0.0259 1.0000 Uani . . O9 O 0.8966(5) 0.04553(11) 1.1025(3) 0.0347 1.0000 Uani . . O10 O 0.6606(5) 0.07748(9) 1.2617(3) 0.0284 1.0000 Uani . . H11 H 0.9863 0.2501 0.2758 0.0379 1.0000 Uiso . . H21 H 1.0184 0.3170 0.4269 0.0403 1.0000 Uiso . . H22 H 0.8066 0.3306 0.2852 0.0403 1.0000 Uiso . . H31 H 0.6747 0.3493 0.4925 0.0405 1.0000 Uiso . . H32 H 0.4814 0.3132 0.3874 0.0405 1.0000 Uiso . . H41 H 0.5420 0.2786 0.6075 0.0292 1.0000 Uiso . . H51 H 0.5291 0.2208 0.4447 0.0328 1.0000 Uiso . . H61 H 0.6439 0.1900 0.6756 0.0374 1.0000 Uiso . . H62 H 0.7899 0.1583 0.5852 0.0374 1.0000 Uiso . . H71 H 1.0614 0.1831 0.8023 0.0361 1.0000 Uiso . . H72 H 1.1557 0.2025 0.6721 0.0361 1.0000 Uiso . . H81 H 1.1954 0.2680 0.8089 0.0334 1.0000 Uiso . . H91 H 0.4081 0.1965 0.1053 0.0469 1.0000 Uiso . . H92 H 0.7084 0.1907 0.1269 0.0469 1.0000 Uiso . . H93 H 0.5855 0.1772 0.2521 0.0469 1.0000 Uiso . . H111 H 0.5612 0.3427 0.8905 0.0404 1.0000 Uiso . . H121 H 0.6417 0.4222 0.9927 0.0458 1.0000 Uiso . . H131 H 1.0431 0.4402 1.1510 0.0448 1.0000 Uiso . . H141 H 1.3734 0.3798 1.1925 0.0435 1.0000 Uiso . . H151 H 1.2903 0.3012 1.0877 0.0363 1.0000 Uiso . . H161 H -0.0552 0.0610 0.5250 0.0346 1.0000 Uiso . . H171 H 0.0493 -0.0071 0.6722 0.0390 1.0000 Uiso . . H172 H 0.1171 -0.0201 0.5286 0.0390 1.0000 Uiso . . H181 H 0.4613 -0.0410 0.7294 0.0382 1.0000 Uiso . . H182 H 0.5484 -0.0020 0.6302 0.0382 1.0000 Uiso . . H191 H 0.7055 0.0261 0.8559 0.0302 1.0000 Uiso . . H201 H 0.5733 0.0873 0.7034 0.0281 1.0000 Uiso . . H211 H 0.6817 0.1129 0.9403 0.0287 1.0000 Uiso . . H212 H 0.4574 0.1476 0.8526 0.0287 1.0000 Uiso . . H221 H 0.3672 0.1191 1.0583 0.0335 1.0000 Uiso . . H222 H 0.1578 0.1002 0.9217 0.0335 1.0000 Uiso . . H231 H 0.2536 0.0340 1.0590 0.0290 1.0000 Uiso . . H241 H 0.3306 0.1160 0.3515 0.0399 1.0000 Uiso . . H242 H 0.2868 0.1354 0.4959 0.0399 1.0000 Uiso . . H243 H 0.0491 0.1176 0.3717 0.0399 1.0000 Uiso . . H261 H 0.9536 -0.0426 1.1427 0.0325 1.0000 Uiso . . H271 H 0.9676 -0.1216 1.2482 0.0387 1.0000 Uiso . . H281 H 0.7108 -0.1365 1.4002 0.0414 1.0000 Uiso . . H291 H 0.4335 -0.0755 1.4435 0.0400 1.0000 Uiso . . H301 H 0.4359 0.0032 1.3437 0.0325 1.0000 Uiso . . 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 C1 0.0326(19) 0.0287(17) 0.0318(19) -0.0028(17) 0.0097(15) 0.0008(17) C2 0.042(2) 0.0243(18) 0.034(2) -0.0020(15) 0.0108(17) -0.0044(16) C3 0.041(2) 0.0190(17) 0.039(2) 0.0018(16) 0.0111(18) 0.0048(16) C4 0.0236(19) 0.0245(17) 0.031(2) -0.0015(14) 0.0098(15) 0.0019(14) C5 0.0263(19) 0.0239(17) 0.0279(19) -0.0004(15) 0.0060(14) -0.0020(14) C6 0.036(2) 0.0242(17) 0.038(2) -0.0001(16) 0.0129(17) 0.0002(16) C7 0.033(2) 0.0317(19) 0.031(2) 0.0021(16) 0.0097(16) 0.0118(16) C8 0.0165(15) 0.0332(17) 0.0310(18) 0.0028(17) 0.0112(13) 0.0027(16) C9 0.043(2) 0.0278(18) 0.035(2) -0.0065(16) 0.0091(18) -0.0045(17) C10 0.0228(18) 0.0283(18) 0.0255(18) 0.0037(15) 0.0073(14) 0.0019(15) C11 0.0224(18) 0.038(2) 0.035(2) 0.0071(16) 0.0130(16) 0.0031(16) C12 0.038(2) 0.035(2) 0.043(2) 0.0100(18) 0.0187(18) 0.0115(18) C13 0.040(2) 0.0307(19) 0.040(2) -0.0005(17) 0.0194(18) -0.0002(17) C14 0.038(2) 0.037(2) 0.030(2) -0.0006(16) 0.0086(16) -0.0054(17) C15 0.028(2) 0.034(2) 0.030(2) -0.0004(16) 0.0075(16) 0.0016(16) C16 0.0261(18) 0.033(2) 0.0268(18) -0.0010(14) 0.0071(14) 0.0058(15) C17 0.035(2) 0.0284(19) 0.035(2) 0.0001(17) 0.0011(17) 0.0008(17) C18 0.036(2) 0.0265(18) 0.034(2) -0.0036(16) 0.0060(16) 0.0065(16) C19 0.0240(18) 0.0273(17) 0.0260(18) -0.0002(14) 0.0120(14) 0.0028(14) C20 0.0203(17) 0.0235(17) 0.0289(19) 0.0038(15) 0.0095(14) 0.0030(14) C21 0.0248(18) 0.0234(16) 0.0264(18) 0.0031(14) 0.0066(13) 0.0012(15) C22 0.0243(19) 0.0252(18) 0.033(2) -0.0015(15) 0.0089(15) 0.0066(14) C23 0.0190(15) 0.0259(16) 0.0298(17) -0.0010(17) 0.0098(13) 0.0017(16) C24 0.038(2) 0.031(2) 0.036(2) 0.0039(17) 0.0104(17) 0.0009(18) C25 0.0194(17) 0.0229(17) 0.0262(18) -0.0010(14) 0.0065(13) -0.0001(13) C26 0.0220(18) 0.0295(19) 0.0307(19) -0.0027(15) 0.0068(15) 0.0024(15) C27 0.033(2) 0.0261(18) 0.039(2) -0.0050(16) 0.0038(16) 0.0102(16) C28 0.038(2) 0.0218(17) 0.036(2) 0.0010(16) -0.0001(17) 0.0002(16) C29 0.036(2) 0.0302(19) 0.036(2) 0.0051(17) 0.0124(17) -0.0044(16) C30 0.0270(18) 0.0244(17) 0.031(2) 0.0003(15) 0.0119(15) 0.0034(15) S1 0.0199(4) 0.0301(5) 0.0321(5) 0.0009(4) 0.0096(4) -0.0018(4) S2 0.0173(4) 0.0244(4) 0.0286(4) 0.0018(4) 0.0094(3) -0.0000(4) O1 0.0404(16) 0.0264(13) 0.0331(14) -0.0020(11) 0.0035(11) 0.0017(12) O2 0.0307(14) 0.0244(12) 0.0322(14) -0.001(1) 0.0085(11) 0.0041(11) O3 0.0279(14) 0.0228(12) 0.0304(14) -0.003(1) 0.0093(11) -0.005(1) O4 0.0150(12) 0.0480(16) 0.0468(16) -0.0026(14) 0.0122(11) -0.0051(13) O5 0.0372(16) 0.0303(14) 0.0377(16) 0.0045(12) 0.0092(12) 0.0018(12) O6 0.0377(16) 0.0327(13) 0.0311(14) 0.0027(11) 0.0134(11) 0.0062(12) O7 0.0238(13) 0.0268(12) 0.0274(13) 0.001(1) 0.0052(11) 0.006(1) O8 0.0258(13) 0.0233(12) 0.0281(13) 0.000(1) 0.006(1) 0.001(1) O9 0.0247(13) 0.0397(14) 0.0428(15) 0.0064(14) 0.0146(11) -0.0011(14) O10 0.0306(14) 0.0249(13) 0.0300(14) -0.0039(11) 0.0089(11) -0.0007(11) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . H11 . 1.013 no C1 . O2 . 1.411(5) yes C1 . O1 . 1.403(5) yes C1 . C2 . 1.523(5) yes C2 . H22 . 1.010 no C2 . H21 . 1.002 no C2 . C3 . 1.535(6) yes C3 . H32 . 1.020 no C3 . H31 . 1.007 no C3 . C4 . 1.518(5) yes C4 . H41 . 1.016 no C4 . O3 . 1.453(5) yes C4 . C5 . 1.522(5) yes C5 . H51 . 1.011 no C5 . O2 . 1.426(5) yes C5 . C6 . 1.514(5) yes C6 . H62 . 0.998 no C6 . H61 . 1.014 no C6 . C7 . 1.512(6) yes C7 . H72 . 1.020 no C7 . H71 . 1.009 no C7 . C8 . 1.515(5) yes C8 . H81 . 1.012 no C8 . O3 . 1.409(4) yes C8 . S1 . 1.823(3) yes C9 . H93 . 1.003 no C9 . H92 . 1.007 no C9 . H91 . 1.020 no C9 . O1 . 1.435(4) yes C10 . S1 . 1.772(4) yes C10 . C15 . 1.393(5) yes C10 . C11 . 1.386(5) yes C11 . H111 . 1.027 no C11 . C12 . 1.382(6) yes C12 . H121 . 1.022 no C12 . C13 . 1.390(6) yes C13 . H131 . 1.025 no C13 . C14 . 1.392(6) yes C14 . H141 . 1.017 no C14 . C15 . 1.379(6) yes C15 . H151 . 1.020 no C16 . H161 . 1.022 no C16 . O7 . 1.424(4) yes C16 . O6 . 1.395(4) yes C16 . C17 . 1.507(5) yes C17 . H172 . 1.013 no C17 . H171 . 1.022 no C17 . C18 . 1.534(6) yes C18 . H182 . 1.016 no C18 . H181 . 0.999 no C18 . C19 . 1.510(5) yes C19 . H191 . 1.008 no C19 . O8 . 1.452(4) yes C19 . C20 . 1.530(5) yes C20 . H201 . 1.014 no C20 . O7 . 1.446(4) yes C20 . C21 . 1.507(5) yes C21 . H212 . 1.006 no C21 . H211 . 1.014 no C21 . C22 . 1.521(5) yes C22 . H222 . 1.023 no C22 . H221 . 1.000 no C22 . C23 . 1.514(5) yes C23 . H231 . 1.003 no C23 . O8 . 1.408(4) yes C23 . S2 . 1.823(3) yes C24 . H243 . 1.015 no C24 . H242 . 0.994 no C24 . H241 . 1.011 no C24 . O6 . 1.425(5) yes C25 . S2 . 1.765(4) yes C25 . C30 . 1.375(5) yes C25 . C26 . 1.401(5) yes C26 . H261 . 1.009 no C26 . C27 . 1.390(5) yes C27 . H271 . 1.020 no C27 . C28 . 1.373(6) yes C28 . H281 . 1.008 no C28 . C29 . 1.383(6) yes C29 . H291 . 1.018 no C29 . C30 . 1.393(5) yes C30 . H301 . 1.002 no S1 . O5 . 1.440(3) yes S1 . O4 . 1.448(3) yes S2 . O10 . 1.441(3) yes S2 . O9 . 1.445(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H11 . C1 . O2 . 105.826 no H11 . C1 . O1 . 110.588 no O2 . C1 . O1 . 112.4(3) yes H11 . C1 . C2 . 111.212 no O2 . C1 . C2 . 110.3(3) yes O1 . C1 . C2 . 106.6(3) yes H22 . C2 . H21 . 108.466 no H22 . C2 . C3 . 109.601 no H21 . C2 . C3 . 109.006 no H22 . C2 . C1 . 109.085 no H21 . C2 . C1 . 109.860 no C3 . C2 . C1 . 110.8(3) yes H32 . C3 . H31 . 107.334 no H32 . C3 . C4 . 108.363 no H31 . C3 . C4 . 109.905 no H32 . C3 . C2 . 109.225 no H31 . C3 . C2 . 110.240 no C4 . C3 . C2 . 111.7(3) yes H41 . C4 . O3 . 108.384 no H41 . C4 . C5 . 107.215 no O3 . C4 . C5 . 112.5(3) yes H41 . C4 . C3 . 112.401 no O3 . C4 . C3 . 105.8(3) yes C5 . C4 . C3 . 110.6(3) yes H51 . C5 . O2 . 110.177 no H51 . C5 . C6 . 111.230 no O2 . C5 . C6 . 106.3(3) yes H51 . C5 . C4 . 106.109 no O2 . C5 . C4 . 112.2(3) yes C6 . C5 . C4 . 110.9(3) yes H62 . C6 . H61 . 108.462 no H62 . C6 . C7 . 109.888 no H61 . C6 . C7 . 107.508 no H62 . C6 . C5 . 110.992 no H61 . C6 . C5 . 110.242 no C7 . C6 . C5 . 109.7(3) yes H72 . C7 . H71 . 107.235 no H72 . C7 . C8 . 109.261 no H71 . C7 . C8 . 109.764 no H72 . C7 . C6 . 107.919 no H71 . C7 . C6 . 109.850 no C8 . C7 . C6 . 112.6(3) yes H81 . C8 . O3 . 103.797 no H81 . C8 . S1 . 109.592 no O3 . C8 . S1 . 111.2(2) yes H81 . C8 . C7 . 107.307 no O3 . C8 . C7 . 115.0(3) yes S1 . C8 . C7 . 109.7(3) yes H93 . C9 . H92 . 108.631 no H93 . C9 . H91 . 107.633 no H92 . C9 . H91 . 107.310 no H93 . C9 . O1 . 111.396 no H92 . C9 . O1 . 111.388 no H91 . C9 . O1 . 110.319 no S1 . C10 . C15 . 118.9(3) yes S1 . C10 . C11 . 119.1(3) yes C15 . C10 . C11 . 121.9(4) yes H111 . C11 . C12 . 122.272 no H111 . C11 . C10 . 119.006 no C12 . C11 . C10 . 118.7(4) yes H121 . C12 . C13 . 120.956 no H121 . C12 . C11 . 118.780 no C13 . C12 . C11 . 120.3(4) yes H131 . C13 . C14 . 120.294 no H131 . C13 . C12 . 119.501 no C14 . C13 . C12 . 120.2(4) yes H141 . C14 . C15 . 118.642 no H141 . C14 . C13 . 121.103 no C15 . C14 . C13 . 120.3(4) yes H151 . C15 . C14 . 122.173 no H151 . C15 . C10 . 119.164 no C14 . C15 . C10 . 118.7(4) yes H161 . C16 . O7 . 106.297 no H161 . C16 . O6 . 108.054 no O7 . C16 . O6 . 112.2(3) yes H161 . C16 . C17 . 110.361 no O7 . C16 . C17 . 111.0(3) yes O6 . C16 . C17 . 108.8(3) yes H172 . C17 . H171 . 106.703 no H172 . C17 . C18 . 110.320 no H171 . C17 . C18 . 109.299 no H172 . C17 . C16 . 110.533 no H171 . C17 . C16 . 109.994 no C18 . C17 . C16 . 109.9(3) yes H182 . C18 . H181 . 108.253 no H182 . C18 . C19 . 107.658 no H181 . C18 . C19 . 108.859 no H182 . C18 . C17 . 108.868 no H181 . C18 . C17 . 111.362 no C19 . C18 . C17 . 111.7(3) yes H191 . C19 . O8 . 107.910 no H191 . C19 . C20 . 106.298 no O8 . C19 . C20 . 113.1(3) yes H191 . C19 . C18 . 112.359 no O8 . C19 . C18 . 106.9(3) yes C20 . C19 . C18 . 110.4(3) yes H201 . C20 . O7 . 109.776 no H201 . C20 . C21 . 111.813 no O7 . C20 . C21 . 106.3(3) yes H201 . C20 . C19 . 106.322 no O7 . C20 . C19 . 111.8(3) yes C21 . C20 . C19 . 111.0(3) yes H212 . C21 . H211 . 107.869 no H212 . C21 . C22 . 110.452 no H211 . C21 . C22 . 108.247 no H212 . C21 . C20 . 110.924 no H211 . C21 . C20 . 110.335 no C22 . C21 . C20 . 109.0(3) yes H222 . C22 . H221 . 107.673 no H222 . C22 . C23 . 109.450 no H221 . C22 . C23 . 110.758 no H222 . C22 . C21 . 107.385 no H221 . C22 . C21 . 109.919 no C23 . C22 . C21 . 111.5(3) yes H231 . C23 . O8 . 104.225 no H231 . C23 . S2 . 109.395 no O8 . C23 . S2 . 111.8(2) yes H231 . C23 . C22 . 107.077 no O8 . C23 . C22 . 114.7(3) yes S2 . C23 . C22 . 109.4(3) yes H243 . C24 . H242 . 108.734 no H243 . C24 . H241 . 107.412 no H242 . C24 . H241 . 109.027 no H243 . C24 . O6 . 110.300 no H242 . C24 . O6 . 111.136 no H241 . C24 . O6 . 110.139 no S2 . C25 . C30 . 119.1(3) yes S2 . C25 . C26 . 119.0(3) yes C30 . C25 . C26 . 121.8(3) yes H261 . C26 . C27 . 122.365 no H261 . C26 . C25 . 119.059 no C27 . C26 . C25 . 118.6(4) yes H271 . C27 . C28 . 121.470 no H271 . C27 . C26 . 119.067 no C28 . C27 . C26 . 119.5(3) yes H281 . C28 . C29 . 118.991 no H281 . C28 . C27 . 119.186 no C29 . C28 . C27 . 121.8(4) yes H291 . C29 . C30 . 118.922 no H291 . C29 . C28 . 121.584 no C30 . C29 . C28 . 119.5(4) yes H301 . C30 . C25 . 120.161 no H301 . C30 . C29 . 120.949 no C25 . C30 . C29 . 118.8(3) yes O5 . S1 . O4 . 119.18(17) yes O5 . S1 . C10 . 107.48(17) yes O4 . S1 . C10 . 108.13(18) yes O5 . S1 . C8 . 105.91(18) yes O4 . S1 . C8 . 109.97(16) yes C10 . S1 . C8 . 105.32(17) yes O10 . S2 . O9 . 119.60(17) yes O10 . S2 . C25 . 107.26(17) yes O9 . S2 . C25 . 107.78(17) yes O10 . S2 . C23 . 106.28(16) yes O9 . S2 . C23 . 109.99(15) yes C25 . S2 . C23 . 104.98(17) yes C1 . O1 . C9 . 112.6(3) yes C1 . O2 . C5 . 114.4(3) yes C8 . O3 . C4 . 117.9(3) yes C16 . O6 . C24 . 113.7(3) yes C16 . O7 . C20 . 113.7(3) yes C23 . O8 . C19 . 118.0(3) yes