# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 #============================================================================== data_global #============================================================================== _publ_contact_author 'Jonathan Burton' _publ_contact_author_email Jonathan.Burton@chem.ox.ac.uk loop_ _publ_author_name _publ_author_address 'Sheldrake, Helen M.' ; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW. UK. and Institute of Cancer Therapeutics, School of Life Sciences, University of Bradford, West Yorkshire BD7 1DP. UK. ; 'Jamieson, Craig' ; Schering-Plough Corporation, Newhouse, Lanarkshire ML1 5SH. UK. ; 'Pascu, Sofia I.' ; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW. UK. and Department of Chemistry, University of Bath, Bath BA2 7AY. UK. ; 'Burton, Jonathan W.' ; Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW. UK. and Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2008' _ccdc_journal_depnumber '?' _publ_section_title ; Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula ; _publ_section_abstract ; A bidirectional synthesis of the originally proposed structures for the natural products elatenyne and a chloroenyne from Laurencia majuscula is described along with a reassessment of the structures of the halogenated enynes based upon a ^13^C NMR chemical shift/structure correlation. ; #============================================================================== data_sulfone-38 #============================================================================== _audit_creation_date 08-12-10 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'cam172' _chemical_name_systematic . _chemical_melting_point 'not measured' _database_code_depnum_ccdc_archive 'CCDC 698760' _cell_length_a 5.5615(17) _cell_length_b 27.699(8) _cell_length_c 10.094(3) _cell_angle_alpha 90 _cell_angle_beta 105.644(6) _cell_angle_gamma 90 _cell_volume 1497.4(8) _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,y+1/2,-z' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C15 H20 O5 S1 # Dc = 1.39 Fooo = 664.00 Mu = 2.35 M = 624.77 # Found Formula = C15 H20 O5 S1 # Dc = 1.39 FOOO = 664.00 Mu = 2.35 M = 624.77 _chemical_formula_sum 'C15 H20 O5 S1' _chemical_formula_moiety 'C15 H20 O5 S1' _chemical_compound_source . _chemical_formula_weight 312.39 _cell_measurement_reflns_used 3494 _cell_measurement_theta_min 5 _cell_measurement_theta_max 55 _cell_measurement_temperature 150 _exptl_crystal_description 'block' _exptl_crystal_colour 'clear_pale_colourless' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.235 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device 'Unknown' _diffrn_measurement_device_type 'Serial' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'synchrotron' _diffrn_radiation_wavelength 0.68980 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 10048 _reflns_number_total 6771 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections with Friedels Law is 3814 # Number of reflections without Friedels Law is 6771 # Theoretical number of reflections is about 3763 _diffrn_reflns_theta_min 2.033 _diffrn_reflns_theta_max 27.500 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.950 _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 _oxford_diffrn_Wilson_B_factor 2.13 _oxford_diffrn_Wilson_scale 32.03 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.62 _refine_diff_density_max 0.60 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 6755 _refine_ls_number_restraints 1 _refine_ls_number_parameters 380 _oxford_refine_ls_R_factor_ref 0.0763 _refine_ls_wR_factor_ref 0.1238 _refine_ls_goodness_of_fit_ref 1.0051 _refine_ls_shift/su_max 0.000371 # The values computed from all data _oxford_reflns_number_all 6755 _refine_ls_R_factor_all 0.0763 _refine_ls_wR_factor_all 0.1238 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5013 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_gt 0.1102 _refine_ls_abs_structure_Flack -0.04(8) _refine_ls_abs_structure_details 'Flack (1983), 2957 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration 'ad' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.32P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.1555(7) 0.74340(13) 0.6809(4) 0.0308 1.0000 Uani . . . . . . . C2 C 0.1521(8) 0.69144(13) 0.6316(4) 0.0326 1.0000 Uani . . . . . . . C3 C 0.3415(8) 0.68420(13) 0.5488(4) 0.0341 1.0000 Uani . . . . . . . C4 C 0.3136(6) 0.72153(12) 0.4358(4) 0.0255 1.0000 Uani . . . . . . . C5 C 0.2983(7) 0.77202(12) 0.4924(4) 0.0276 1.0000 Uani . . . . . . . C6 C 0.2257(7) 0.80883(12) 0.3777(4) 0.0310 1.0000 Uani . . . . . . . C7 C -0.0189(7) 0.79414(13) 0.2793(4) 0.0328 1.0000 Uani . . . . . . . C8 C -0.0153(6) 0.74250(13) 0.2281(3) 0.0266 1.0000 Uani . . . . . . . C9 C 0.4217(8) 0.79959(13) 0.8261(4) 0.0370 1.0000 Uani . . . . . . . C10 C 0.0795(6) 0.68228(12) 0.0185(4) 0.0257 1.0000 Uani . . . . . . . C11 C 0.2667(7) 0.64817(13) 0.0446(4) 0.0301 1.0000 Uani . . . . . . . C12 C 0.2195(8) 0.60327(13) -0.0159(4) 0.0374 1.0000 Uani . . . . . . . C13 C -0.0119(8) 0.59271(14) -0.1034(4) 0.0363 1.0000 Uani . . . . . . . C14 C -0.2004(8) 0.62750(14) -0.1289(4) 0.0354 1.0000 Uani . . . . . . . C15 C -0.1565(7) 0.67253(13) -0.0701(4) 0.0295 1.0000 Uani . . . . . . . C16 C 0.8707(7) 0.94595(12) 0.4299(4) 0.0290 1.0000 Uani . . . . . . . C17 C 0.8356(8) 0.99819(13) 0.3872(4) 0.0350 1.0000 Uani . . . . . . . C18 C 0.5646(7) 1.00738(13) 0.3064(4) 0.0325 1.0000 Uani . . . . . . . C19 C 0.4811(7) 0.97261(12) 0.1875(4) 0.0246 1.0000 Uani . . . . . . . C20 C 0.5398(6) 0.92053(12) 0.2359(4) 0.0247 1.0000 Uani . . . . . . . C21 C 0.5001(6) 0.88665(12) 0.1152(3) 0.0249 1.0000 Uani . . . . . . . C22 C 0.6588(6) 0.90280(12) 0.0225(4) 0.0261 1.0000 Uani . . . . . . . C23 C 0.6053(6) 0.95483(13) -0.0223(3) 0.0249 1.0000 Uani . . . . . . . C24 C 0.7686(7) 0.88882(13) 0.5785(4) 0.0341 1.0000 Uani . . . . . . . C25 C 0.3126(6) 1.01519(12) -0.2340(4) 0.0225 1.0000 Uani . . . . . . . C26 C 0.1530(7) 1.05046(13) -0.2064(4) 0.0283 1.0000 Uani . . . . . . . C27 C 0.1471(7) 1.09531(12) -0.2687(4) 0.0341 1.0000 Uani . . . . . . . C28 C 0.2945(8) 1.10376(13) -0.3543(4) 0.0372 1.0000 Uani . . . . . . . C29 C 0.4509(8) 1.06872(13) -0.3817(4) 0.0357 1.0000 Uani . . . . . . . C30 C 0.4606(7) 1.02352(12) -0.3213(4) 0.0275 1.0000 Uani . . . . . . . S1 S 0.13964(16) 0.74078(5) 0.09017(9) 0.0278 1.0000 Uani . . . . . . . S2 S 0.31462(14) 0.95730(4) -0.15993(9) 0.0238 1.0000 Uani . . . . . . . O1 O 0.3869(5) 0.75073(9) 0.7772(3) 0.0349 1.0000 Uani . . . . . . . O2 O 0.1168(4) 0.77546(9) 0.5683(2) 0.0287 1.0000 Uani . . . . . . . O3 O 0.0866(5) 0.70852(8) 0.3313(3) 0.0283 1.0000 Uani . . . . . . . O4 O 0.4068(4) 0.74555(10) 0.1471(3) 0.0364 1.0000 Uani . . . . . . . O5 O 0.0096(5) 0.77492(9) -0.0113(3) 0.0350 1.0000 Uani . . . . . . . O6 O 0.7380(5) 0.93680(9) 0.5261(3) 0.0336 1.0000 Uani . . . . . . . O7 O 0.7976(4) 0.91507(9) 0.3134(2) 0.0273 1.0000 Uani . . . . . . . O8 O 0.6030(5) 0.98741(8) 0.0838(2) 0.0258 1.0000 Uani . . . . . . . O9 O 0.1035(4) 0.95454(10) -0.1024(3) 0.0344 1.0000 Uani . . . . . . . O10 O 0.3385(5) 0.92253(9) -0.2616(2) 0.0299 1.0000 Uani . . . . . . . H11 H 0.0218 0.7496 0.7242 0.0363 1.0000 Uiso R . . . . . . H21 H -0.0170 0.6839 0.5729 0.0391 1.0000 Uiso R . . . . . . H22 H 0.1897 0.6703 0.7107 0.0388 1.0000 Uiso R . . . . . . H31 H 0.3196 0.6526 0.5086 0.0407 1.0000 Uiso R . . . . . . H32 H 0.5100 0.6875 0.6088 0.0413 1.0000 Uiso R . . . . . . H41 H 0.4525 0.7204 0.3948 0.0302 1.0000 Uiso R . . . . . . H51 H 0.4587 0.7806 0.5539 0.0323 1.0000 Uiso R . . . . . . H61 H 0.3573 0.8098 0.3296 0.0366 1.0000 Uiso R . . . . . . H62 H 0.2079 0.8409 0.4163 0.0364 1.0000 Uiso R . . . . . . H71 H -0.0605 0.8150 0.2011 0.0395 1.0000 Uiso R . . . . . . H72 H -0.1503 0.7948 0.3255 0.0391 1.0000 Uiso R . . . . . . H81 H -0.1862 0.7321 0.1853 0.0322 1.0000 Uiso R . . . . . . H91 H 0.5589 0.7994 0.9093 0.0551 1.0000 Uiso R . . . . . . H92 H 0.2678 0.8108 0.8455 0.0548 1.0000 Uiso R . . . . . . H93 H 0.4597 0.8202 0.7551 0.0551 1.0000 Uiso R . . . . . . H111 H 0.4215 0.6552 0.1053 0.0359 1.0000 Uiso R . . . . . . H121 H 0.3440 0.5791 0.0003 0.0447 1.0000 Uiso R . . . . . . H131 H -0.0423 0.5621 -0.1470 0.0451 1.0000 Uiso R . . . . . . H141 H -0.3596 0.6199 -0.1889 0.0427 1.0000 Uiso R . . . . . . H151 H -0.2860 0.6967 -0.0884 0.0350 1.0000 Uiso R . . . . . . H161 H 1.0493 0.9389 0.4714 0.0354 1.0000 Uiso R . . . . . . H171 H 0.9447 1.0060 0.3291 0.0414 1.0000 Uiso R . . . . . . H172 H 0.8737 1.0189 0.4676 0.0417 1.0000 Uiso R . . . . . . H181 H 0.5489 1.0400 0.2716 0.0397 1.0000 Uiso R . . . . . . H182 H 0.4582 1.0029 0.3661 0.0390 1.0000 Uiso R . . . . . . H191 H 0.3010 0.9752 0.1490 0.0290 1.0000 Uiso R . . . . . . H201 H 0.4319 0.9123 0.2957 0.0297 1.0000 Uiso R . . . . . . H211 H 0.3287 0.8873 0.0637 0.0304 1.0000 Uiso R . . . . . . H212 H 0.5441 0.8538 0.1522 0.0302 1.0000 Uiso R . . . . . . H221 H 0.6298 0.8823 -0.0591 0.0315 1.0000 Uiso R . . . . . . H222 H 0.8352 0.9004 0.0727 0.0312 1.0000 Uiso R . . . . . . H231 H 0.7358 0.9646 -0.0651 0.0295 1.0000 Uiso R . . . . . . H241 H 0.6814 0.8861 0.6490 0.0518 1.0000 Uiso R . . . . . . H242 H 0.6956 0.8668 0.5043 0.0510 1.0000 Uiso R . . . . . . H243 H 0.9410 0.8807 0.6150 0.0510 1.0000 Uiso R . . . . . . H261 H 0.0518 1.0442 -0.1467 0.0329 1.0000 Uiso R . . . . . . H271 H 0.0428 1.1197 -0.2498 0.0411 1.0000 Uiso R . . . . . . H281 H 0.2930 1.1345 -0.3943 0.0451 1.0000 Uiso R . . . . . . H291 H 0.5514 1.0751 -0.4392 0.0426 1.0000 Uiso R . . . . . . H301 H 0.5628 0.9995 -0.3416 0.0329 1.0000 Uiso R . . . . . . 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 0.0344(19) 0.0280(16) 0.0308(19) -0.0031(16) 0.0102(15) 0.0026(16) C2 0.043(2) 0.0249(17) 0.032(2) -0.0010(14) 0.0135(17) -0.0014(15) C3 0.045(2) 0.0186(16) 0.040(2) 0.0011(15) 0.0136(18) 0.0054(16) C4 0.0228(18) 0.0255(16) 0.0294(19) 0.0007(14) 0.0093(14) 0.0005(13) C5 0.0234(17) 0.0235(16) 0.035(2) -0.0001(15) 0.0059(15) -0.0010(13) C6 0.037(2) 0.0234(16) 0.035(2) -0.0001(15) 0.0141(17) 0.0012(15) C7 0.035(2) 0.0307(18) 0.034(2) 0.0023(16) 0.0117(17) 0.0112(15) C8 0.0187(15) 0.0311(16) 0.0311(18) 0.0022(16) 0.0086(13) 0.0034(15) C9 0.044(2) 0.0288(18) 0.036(2) -0.0051(16) 0.0075(18) -0.0028(16) C10 0.0213(17) 0.0290(17) 0.0293(19) 0.0034(15) 0.0111(14) 0.0018(14) C11 0.0230(17) 0.0366(19) 0.033(2) 0.0100(15) 0.0116(15) 0.0027(15) C12 0.037(2) 0.033(2) 0.046(2) 0.0110(18) 0.0182(18) 0.0128(17) C13 0.043(2) 0.0297(18) 0.042(2) 0.0003(17) 0.0207(18) -0.0006(16) C14 0.038(2) 0.0361(19) 0.033(2) 0.0014(16) 0.0105(16) -0.0059(16) C15 0.0279(19) 0.0295(18) 0.029(2) -0.0019(15) 0.0038(15) 0.0008(14) C16 0.0255(17) 0.0329(19) 0.0280(18) -0.0016(14) 0.0060(14) 0.0048(14) C17 0.040(2) 0.0292(18) 0.031(2) -0.0005(16) 0.0010(17) -0.0018(16) C18 0.036(2) 0.0279(17) 0.033(2) -0.0023(15) 0.0083(16) 0.0066(15) C19 0.0234(17) 0.0257(16) 0.0269(18) -0.0004(13) 0.0104(14) 0.0042(13) C20 0.0214(16) 0.0252(16) 0.0302(19) 0.0063(14) 0.0113(14) 0.0021(13) C21 0.0245(17) 0.0234(16) 0.0266(18) 0.0042(14) 0.0063(14) 0.0021(14) C22 0.0225(17) 0.0272(17) 0.0311(19) -0.0004(14) 0.0115(14) 0.0068(13) C23 0.0163(14) 0.0276(15) 0.0327(17) -0.0017(16) 0.0100(13) 0.0010(14) C24 0.038(2) 0.0303(19) 0.035(2) 0.0041(16) 0.0099(17) 0.0030(16) C25 0.0197(16) 0.0230(16) 0.0253(17) -0.0009(13) 0.0069(13) 0.0002(13) C26 0.0239(18) 0.0319(18) 0.0293(19) -0.0028(14) 0.0077(15) 0.0028(14) C27 0.030(2) 0.0282(18) 0.040(2) -0.0034(16) 0.0026(16) 0.0095(15) C28 0.047(2) 0.0218(17) 0.038(2) 0.0006(16) 0.0044(18) 0.0003(16) C29 0.041(2) 0.0304(18) 0.040(2) 0.0022(16) 0.0176(18) -0.0056(16) C30 0.0271(17) 0.0239(16) 0.033(2) 0.0001(14) 0.0098(15) 0.0030(14) S1 0.0205(4) 0.0308(4) 0.0332(5) 0.0011(4) 0.0092(3) -0.0018(4) S2 0.0185(4) 0.0245(4) 0.0302(4) 0.0016(4) 0.0098(3) -0.0001(3) O1 0.0401(15) 0.0268(13) 0.0342(14) 0.0003(11) 0.0036(11) 0.0024(11) O2 0.0296(13) 0.0243(11) 0.0333(14) 0.0001(10) 0.0100(11) 0.0033(10) O3 0.0291(14) 0.0231(11) 0.0329(14) -0.0021(10) 0.0088(11) -0.0054(10) O4 0.0155(11) 0.0479(15) 0.0474(16) -0.0040(13) 0.0110(10) -0.0049(12) O5 0.0385(15) 0.0296(13) 0.0364(15) 0.0056(11) 0.0094(12) 0.0003(11) O6 0.0371(15) 0.0338(13) 0.0320(14) 0.0020(11) 0.0132(11) 0.0067(11) O7 0.0254(13) 0.0269(12) 0.0281(13) 0.0002(10) 0.0049(10) 0.0054(10) O8 0.0276(13) 0.0229(11) 0.0268(13) -0.0006(9) 0.0073(10) 0.0001(9) O9 0.0237(12) 0.0410(13) 0.0420(14) 0.0059(13) 0.0147(10) -0.0011(12) O10 0.0324(14) 0.0246(12) 0.0331(14) -0.0028(10) 0.0095(11) -0.0007(10) _refine_ls_extinction_method 'None' _oxford_refine_ls_scale 0.17938(10) 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 . C2 . 1.521(5) yes C1 . O1 . 1.403(4) yes C1 . O2 . 1.412(4) yes C1 . H11 . 0.975 no C2 . C3 . 1.524(5) yes C2 . H21 . 0.990 no C2 . H22 . 0.966 no C3 . C4 . 1.516(5) yes C3 . H31 . 0.959 no C3 . H32 . 0.973 no C4 . C5 . 1.522(5) yes C4 . O3 . 1.456(4) yes C4 . H41 . 0.970 no C5 . C6 . 1.514(5) yes C5 . O2 . 1.425(4) yes C5 . H51 . 0.969 no C6 . C7 . 1.508(5) yes C6 . H61 . 0.981 no C6 . H62 . 0.986 no C7 . C8 . 1.523(5) yes C7 . H71 . 0.956 no C7 . H72 . 0.967 no C8 . S1 . 1.825(3) yes C8 . O3 . 1.405(4) yes C8 . H81 . 0.976 no C9 . O1 . 1.436(4) yes C9 . H91 . 0.970 no C9 . H92 . 0.978 no C9 . H93 . 0.983 no C10 . C11 . 1.378(5) yes C10 . C15 . 1.401(5) yes C10 . S1 . 1.769(4) yes C11 . C12 . 1.379(5) yes C11 . H111 . 0.933 no C12 . C13 . 1.381(6) yes C12 . H121 . 0.945 no C13 . C14 . 1.396(6) yes C13 . H131 . 0.949 no C14 . C15 . 1.374(5) yes C14 . H141 . 0.951 no C15 . H151 . 0.963 no C16 . C17 . 1.507(5) yes C16 . O6 . 1.393(4) yes C16 . O7 . 1.421(4) yes C16 . H161 . 0.988 no C17 . C18 . 1.529(5) yes C17 . H171 . 0.975 no C17 . H172 . 0.970 no C18 . C19 . 1.511(5) yes C18 . H181 . 0.966 no C18 . H182 . 0.960 no C19 . C20 . 1.530(5) yes C19 . O8 . 1.451(4) yes C19 . H191 . 0.975 no C20 . C21 . 1.506(5) yes C20 . O7 . 1.444(4) yes C20 . H201 . 0.986 no C21 . C22 . 1.516(5) yes C21 . H211 . 0.955 no C21 . H212 . 0.988 no C22 . C23 . 1.516(5) yes C22 . H221 . 0.978 no C22 . H222 . 0.977 no C23 . S2 . 1.827(3) yes C23 . O8 . 1.403(4) yes C23 . H231 . 0.978 no C24 . O6 . 1.423(4) yes C24 . H241 . 0.966 no C24 . H242 . 0.966 no C24 . H243 . 0.956 no C25 . C26 . 1.398(5) yes C25 . C30 . 1.377(5) yes C25 . S2 . 1.768(3) yes C26 . C27 . 1.389(5) yes C26 . H261 . 0.945 no C27 . C28 . 1.362(6) yes C27 . H271 . 0.942 no C28 . C29 . 1.380(6) yes C28 . H281 . 0.940 no C29 . C30 . 1.388(5) yes C29 . H291 . 0.925 no C30 . H301 . 0.934 no S1 . O4 . 1.447(2) yes S1 . O5 . 1.438(3) yes S2 . O9 . 1.446(3) yes S2 . O10 . 1.440(2) 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 C2 . C1 . O1 . 106.9(3) yes C2 . C1 . O2 . 110.3(3) yes O1 . C1 . O2 . 112.3(3) yes C2 . C1 . H11 . 111.7 no O1 . C1 . H11 . 109.4 no O2 . C1 . H11 . 106.4 no C1 . C2 . C3 . 110.8(3) yes C1 . C2 . H21 . 108.7 no C3 . C2 . H21 . 109.3 no C1 . C2 . H22 . 108.8 no C3 . C2 . H22 . 110.2 no H21 . C2 . H22 . 109.1 no C2 . C3 . C4 . 112.2(3) yes C2 . C3 . H31 . 108.9 no C4 . C3 . H31 . 109.2 no C2 . C3 . H32 . 109.8 no C4 . C3 . H32 . 106.8 no H31 . C3 . H32 . 109.9 no C3 . C4 . C5 . 110.4(3) yes C3 . C4 . O3 . 105.6(3) yes C5 . C4 . O3 . 112.0(3) yes C3 . C4 . H41 . 111.6 no C5 . C4 . H41 . 108.7 no O3 . C4 . H41 . 108.5 no C4 . C5 . C6 . 111.2(3) yes C4 . C5 . O2 . 112.5(3) yes C6 . C5 . O2 . 106.5(3) yes C4 . C5 . H51 . 109.4 no C6 . C5 . H51 . 109.5 no O2 . C5 . H51 . 107.6 no C5 . C6 . C7 . 109.2(3) yes C5 . C6 . H61 . 108.4 no C7 . C6 . H61 . 110.0 no C5 . C6 . H62 . 109.8 no C7 . C6 . H62 . 109.5 no H61 . C6 . H62 . 109.8 no C6 . C7 . C8 . 112.6(3) yes C6 . C7 . H71 . 110.8 no C8 . C7 . H71 . 108.1 no C6 . C7 . H72 . 110.0 no C8 . C7 . H72 . 105.2 no H71 . C7 . H72 . 109.9 no C7 . C8 . S1 . 109.6(3) yes C7 . C8 . O3 . 114.7(3) yes S1 . C8 . O3 . 111.7(2) yes C7 . C8 . H81 . 109.1 no S1 . C8 . H81 . 105.0 no O3 . C8 . H81 . 106.3 no O1 . C9 . H91 . 107.1 no O1 . C9 . H92 . 108.8 no H91 . C9 . H92 . 110.8 no O1 . C9 . H93 . 109.5 no H91 . C9 . H93 . 111.2 no H92 . C9 . H93 . 109.5 no C11 . C10 . C15 . 121.3(3) yes C11 . C10 . S1 . 120.0(3) yes C15 . C10 . S1 . 118.6(3) yes C10 . C11 . C12 . 119.3(4) yes C10 . C11 . H111 . 120.0 no C12 . C11 . H111 . 120.6 no C11 . C12 . C13 . 120.5(3) yes C11 . C12 . H121 . 121.3 no C13 . C12 . H121 . 118.2 no C12 . C13 . C14 . 119.7(4) yes C12 . C13 . H131 . 120.3 no C14 . C13 . H131 . 120.0 no C13 . C14 . C15 . 120.6(4) yes C13 . C14 . H141 . 119.3 no C15 . C14 . H141 . 120.1 no C10 . C15 . C14 . 118.5(3) yes C10 . C15 . H151 . 120.8 no C14 . C15 . H151 . 120.7 no C17 . C16 . O6 . 108.8(3) yes C17 . C16 . O7 . 110.8(3) yes O6 . C16 . O7 . 112.3(3) yes C17 . C16 . H161 . 110.4 no O6 . C16 . H161 . 109.2 no O7 . C16 . H161 . 105.3 no C16 . C17 . C18 . 110.2(3) yes C16 . C17 . H171 . 109.4 no C18 . C17 . H171 . 109.0 no C16 . C17 . H172 . 110.3 no C18 . C17 . H172 . 108.0 no H171 . C17 . H172 . 109.9 no C17 . C18 . C19 . 111.4(3) yes C17 . C18 . H181 . 109.3 no C19 . C18 . H181 . 109.3 no C17 . C18 . H182 . 109.3 no C19 . C18 . H182 . 107.9 no H181 . C18 . H182 . 109.7 no C18 . C19 . C20 . 110.7(3) yes C18 . C19 . O8 . 106.8(3) yes C20 . C19 . O8 . 113.3(3) yes C18 . C19 . H191 . 109.4 no C20 . C19 . H191 . 107.8 no O8 . C19 . H191 . 108.7 no C19 . C20 . C21 . 110.9(3) yes C19 . C20 . O7 . 111.5(3) yes C21 . C20 . O7 . 106.3(3) yes C19 . C20 . H201 . 107.5 no C21 . C20 . H201 . 111.7 no O7 . C20 . H201 . 108.9 no C20 . C21 . C22 . 109.4(3) yes C20 . C21 . H211 . 109.6 no C22 . C21 . H211 . 108.6 no C20 . C21 . H212 . 107.5 no C22 . C21 . H212 . 112.2 no H211 . C21 . H212 . 109.4 no C21 . C22 . C23 . 111.4(3) yes C21 . C22 . H221 . 111.0 no C23 . C22 . H221 . 109.0 no C21 . C22 . H222 . 109.3 no C23 . C22 . H222 . 107.9 no H221 . C22 . H222 . 108.2 no C22 . C23 . S2 . 109.0(2) yes C22 . C23 . O8 . 115.2(3) yes S2 . C23 . O8 . 111.6(2) yes C22 . C23 . H231 . 106.6 no S2 . C23 . H231 . 105.2 no O8 . C23 . H231 . 108.7 no O6 . C24 . H241 . 108.3 no O6 . C24 . H242 . 108.6 no H241 . C24 . H242 . 109.3 no O6 . C24 . H243 . 111.6 no H241 . C24 . H243 . 110.3 no H242 . C24 . H243 . 108.7 no C26 . C25 . C30 . 122.1(3) yes C26 . C25 . S2 . 118.8(3) yes C30 . C25 . S2 . 119.1(2) yes C25 . C26 . C27 . 118.3(4) yes C25 . C26 . H261 . 121.3 no C27 . C26 . H261 . 120.4 no C26 . C27 . C28 . 119.7(3) yes C26 . C27 . H271 . 119.3 no C28 . C27 . H271 . 120.9 no C27 . C28 . C29 . 121.7(4) yes C27 . C28 . H281 . 119.4 no C29 . C28 . H281 . 118.8 no C28 . C29 . C30 . 119.9(4) yes C28 . C29 . H291 . 120.7 no C30 . C29 . H291 . 119.4 no C29 . C30 . C25 . 118.3(3) yes C29 . C30 . H301 . 120.0 no C25 . C30 . H301 . 121.7 no C8 . S1 . C10 . 105.04(16) yes C8 . S1 . O4 . 109.88(16) yes C10 . S1 . O4 . 107.86(16) yes C8 . S1 . O5 . 106.03(16) yes C10 . S1 . O5 . 107.93(16) yes O4 . S1 . O5 . 119.22(16) yes C23 . S2 . C25 . 105.01(16) yes C23 . S2 . O9 . 109.90(15) yes C25 . S2 . O9 . 107.74(16) yes C23 . S2 . O10 . 106.53(15) yes C25 . S2 . O10 . 107.24(16) yes O9 . S2 . O10 . 119.50(16) yes C9 . O1 . C1 . 112.8(3) yes C5 . O2 . C1 . 114.5(3) yes C4 . O3 . C8 . 118.0(2) yes C24 . O6 . C16 . 113.3(3) yes C20 . O7 . C16 . 113.9(2) yes C19 . O8 . C23 . 118.1(2) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . O4 . 122 0.97 2.54 3.165(5) yes C8 . H81 . O4 1_455 148 0.98 2.22 3.096(5) yes C9 . H91 . O5 1_656 140 0.97 2.51 3.310(5) yes C9 . H92 . O5 1_556 131 0.98 2.50 3.232(5) yes C15 . H151 . O1 1_454 159 0.96 2.46 3.377(5) yes C19 . H191 . O9 . 120 0.97 2.54 3.148(5) yes C21 . H211 . O9 . 127 0.96 2.59 3.258(5) yes C23 . H231 . O9 1_655 151 0.98 2.19 3.089(5) yes C24 . H241 . O10 1_556 144 0.97 2.53 3.359(5) yes C24 . H243 . O10 1_656 138 0.96 2.51 3.281(5) yes C30 . H301 . O6 1_554 161 0.93 2.54 3.436(5) yes