Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_publication_text _journal_coden_Cambridge 177 _ccdc_journal_manuscript_code B509193D _publ_requested_journal Org.Biomol.Chem. _publ_contact_author_name 'Suzanne R. Abrams' _publ_contact_author_address ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; _publ_contact_author_email sue.abrams@nrc-cnrc.gc.ca _publ_contact_author_phone 011(306)9755333 _publ_contact_author_fax 011(306)9754839 loop_ _publ_author_name _publ_author_address 'Abrams, Suzanne R.' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Nyangulu, James M.' ;Department of Chemistry St. Francis Xavier University PO Box 5000 Antigonish, NS Canada B2G 2W5 ; 'Rose, Patricia A.' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Gai, Yuanzhu' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Nelson, Ken M.' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Loewen, Mary' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Cutler, Adrian J.' ;Plant Biotechnology Institute National Research Council of Canada 110 Gymnasium Pl Saskatoon, SK Canada S7N 0W9 ; 'Quail, J. Wilson' ;Department of Chemistry Saskatchewan Structural Sciences Centre University of Saskatchewan 110 Science Pl Saskatoon, SK Canada S7N 5C9 ; data_yg _database_code_depnum_ccdc_archive 'CCDC 278290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H45 N5 O4 S, 2 (C H4 O)' _chemical_formula_sum 'C38 H53 N5 O6 S' _chemical_formula_weight 707.91 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.2340(2) _cell_length_b 16.3940(2) _cell_length_c 20.9930(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3866.28(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16903 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description chip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 32824 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4913 _reflns_number_gt 4217 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'maXus(Mackay et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xtal3.7(Hall et al., 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.5450P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.39(9) _refine_ls_number_reflns 4913 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.26049(6) 0.19172(4) -0.04378(3) 0.02793(15) Uani 1 1 d . . . O1 O 0.30681(18) 0.17238(12) -0.10551(9) 0.0348(4) Uani 1 1 d . . . O2 O 0.20475(18) 0.26934(11) -0.03380(9) 0.0350(5) Uani 1 1 d . . . O3 O 0.86764(17) 0.16878(11) 0.16681(8) 0.0310(4) Uani 1 1 d . . . H3O H 0.8480 0.2166 0.1571 0.047 Uiso 1 1 calc R . . O4 O 1.5169(2) -0.04258(19) 0.29358(12) 0.0649(8) Uani 1 1 d . . . O100 O 0.55504(19) 0.07432(14) -0.02129(12) 0.0490(6) Uani 1 1 d . . . H100 H 0.6001 0.1002 -0.0460 0.074 Uiso 1 1 calc R . . O101 O 0.1800(2) 0.33520(13) 0.10219(10) 0.0428(5) Uani 1 1 d . . . H101 H 0.2301 0.3006 0.0898 0.064 Uiso 1 1 calc R . . N1 N 0.37600(18) 0.18714(14) 0.00370(10) 0.0288(5) Uani 1 1 d . . . H1 H 0.4471 0.1724 -0.0096 0.035 Uiso 1 1 calc R . . N2 N 0.35291(19) 0.20840(13) 0.06676(10) 0.0291(5) Uani 1 1 d . . . N3 N 0.0093(3) -0.16372(15) -0.00485(13) 0.0469(7) Uani 1 1 d . . . N4 N 1.2009(2) 0.08611(13) 0.24706(11) 0.0303(5) Uani 1 1 d . . . N5 N 1.2389(2) 0.01541(14) 0.21467(11) 0.0327(5) Uani 1 1 d . . . C1 C 0.1580(2) 0.11580(16) -0.01894(12) 0.0264(5) Uani 1 1 d . . . C2 C 0.0576(2) 0.14256(17) 0.01133(13) 0.0313(6) Uani 1 1 d . . . H2 H 0.0453 0.1994 0.0173 0.038 Uiso 1 1 calc R . . C3 C -0.0274(3) 0.08687(18) 0.03370(14) 0.0351(6) Uani 1 1 d . . . H3 H -0.0958 0.1057 0.0558 0.042 Uiso 1 1 calc R . . C4 C -0.0111(3) 0.00518(18) 0.02344(13) 0.0343(6) Uani 1 1 d . . . H4 H -0.0689 -0.0322 0.0388 0.041 Uiso 1 1 calc R . . C5 C 0.0895(2) -0.02495(16) -0.00949(13) 0.0297(6) Uani 1 1 d . . . C6 C 0.1040(3) -0.11100(17) -0.02204(14) 0.0352(6) Uani 1 1 d . . . C7 C 0.2086(3) -0.13755(17) -0.04790(15) 0.0388(7) Uani 1 1 d . . . H7 H 0.2204 -0.1943 -0.0543 0.047 Uiso 1 1 calc R . . C8 C 0.2992(3) -0.08288(18) -0.06528(14) 0.0368(7) Uani 1 1 d . . . H8 H 0.3714 -0.1034 -0.0825 0.044 Uiso 1 1 calc R . . C9 C 0.2852(2) -0.00036(17) -0.05783(13) 0.0317(6) Uani 1 1 d . . . H9 H 0.3462 0.0359 -0.0713 0.038 Uiso 1 1 calc R . . C10 C 0.1796(2) 0.03072(16) -0.02991(12) 0.0259(5) Uani 1 1 d . . . C11 C 0.4413(2) 0.19790(16) 0.10542(13) 0.0289(6) Uani 1 1 d . . . H11 H 0.5156 0.1784 0.0902 0.035 Uiso 1 1 calc R . . C12 C 0.4252(2) 0.21625(17) 0.17194(14) 0.0311(6) Uani 1 1 d . . . H12 H 0.3481 0.2337 0.1846 0.037 Uiso 1 1 calc R . . C13 C 0.5080(2) 0.21120(16) 0.21810(13) 0.0284(6) Uani 1 1 d . . . C14 C 0.6322(2) 0.19089(16) 0.20468(13) 0.0282(5) Uani 1 1 d . . . H14 H 0.6555 0.1883 0.1612 0.034 Uiso 1 1 calc R . . C15 C 0.7152(2) 0.17580(16) 0.24820(13) 0.0297(6) Uani 1 1 d . . . H15 H 0.6925 0.1784 0.2918 0.036 Uiso 1 1 calc R . . C16 C 0.8434(2) 0.15477(16) 0.23317(12) 0.0269(5) Uani 1 1 d . . . C17 C 0.8672(2) 0.06166(17) 0.24370(14) 0.0322(6) Uani 1 1 d . . . C18 C 0.9943(2) 0.04434(16) 0.22077(14) 0.0323(6) Uani 1 1 d . . . H18A H 1.0150 -0.0126 0.2320 0.039 Uiso 1 1 calc R . . H18B H 0.9960 0.0487 0.1737 0.039 Uiso 1 1 calc R . . C19 C 1.0876(2) 0.09970(16) 0.24759(13) 0.0284(6) Uani 1 1 d . . . C20 C 1.0489(2) 0.17631(16) 0.27947(12) 0.0280(5) Uani 1 1 d . . . C21 C 1.1295(3) 0.22154(17) 0.31615(13) 0.0336(6) Uani 1 1 d . . . H21 H 1.2089 0.2027 0.3210 0.040 Uiso 1 1 calc R . . C22 C 1.0949(3) 0.29324(18) 0.34530(15) 0.0405(7) Uani 1 1 d . . . H22 H 1.1500 0.3231 0.3705 0.049 Uiso 1 1 calc R . . C23 C 0.9790(3) 0.32162(19) 0.33769(15) 0.0441(7) Uani 1 1 d . . . H23 H 0.9549 0.3710 0.3575 0.053 Uiso 1 1 calc R . . C24 C 0.8993(3) 0.27790(18) 0.30131(14) 0.0379(7) Uani 1 1 d . . . H24 H 0.8211 0.2985 0.2954 0.046 Uiso 1 1 calc R . . C25 C 0.9310(2) 0.20374(16) 0.27285(13) 0.0288(6) Uani 1 1 d . . . C26 C 1.2212(3) 0.01680(19) 0.14436(13) 0.0365(7) Uani 1 1 d . . . H26A H 1.2150 0.0737 0.1289 0.044 Uiso 1 1 calc R . . H26B H 1.1474 -0.0126 0.1327 0.044 Uiso 1 1 calc R . . C27 C 1.3279(3) -0.0245(3) 0.11567(18) 0.0586(10) Uani 1 1 d . . . H27A H 1.3754 0.0147 0.0904 0.070 Uiso 1 1 calc R . . H27B H 1.3030 -0.0700 0.0877 0.070 Uiso 1 1 calc R . . C28 C 1.3991(3) -0.0560(2) 0.17147(18) 0.0515(9) Uani 1 1 d . . . H28A H 1.4855 -0.0549 0.1621 0.062 Uiso 1 1 calc R . . H28B H 1.3755 -0.1125 0.1825 0.062 Uiso 1 1 calc R . . C29 C 1.3681(2) 0.00283(18) 0.22499(15) 0.0365(7) Uani 1 1 d . . . H29 H 1.4115 0.0555 0.2187 0.044 Uiso 1 1 calc R . . C30 C -0.0992(3) -0.1552(2) -0.04287(19) 0.0595(10) Uani 1 1 d . . . H30A H -0.1673 -0.1760 -0.0186 0.071 Uiso 1 1 calc R . . H30B H -0.0909 -0.1865 -0.0824 0.071 Uiso 1 1 calc R . . H30C H -0.1120 -0.0976 -0.0531 0.071 Uiso 1 1 calc R . . C31 C 0.0419(4) -0.2493(2) 0.0028(3) 0.0706(12) Uani 1 1 d . . . H31A H -0.0256 -0.2794 0.0207 0.085 Uiso 1 1 calc R . . H31B H 0.1102 -0.2535 0.0316 0.085 Uiso 1 1 calc R . . H31C H 0.0629 -0.2723 -0.0387 0.085 Uiso 1 1 calc R . . C32 C 0.4727(3) 0.2254(2) 0.28619(14) 0.0402(7) Uani 1 1 d . . . H32A H 0.5289 0.2633 0.3061 0.048 Uiso 1 1 calc R . . H32B H 0.4737 0.1734 0.3093 0.048 Uiso 1 1 calc R . . H32C H 0.3924 0.2486 0.2877 0.048 Uiso 1 1 calc R . . C33 C 0.7814(3) 0.00934(18) 0.20474(17) 0.0427(7) Uani 1 1 d . . . H33A H 0.6999 0.0180 0.2199 0.051 Uiso 1 1 calc R . . H33B H 0.8026 -0.0483 0.2096 0.051 Uiso 1 1 calc R . . H33C H 0.7868 0.0247 0.1597 0.051 Uiso 1 1 calc R . . C34 C 0.8539(3) 0.03893(19) 0.31464(15) 0.0415(7) Uani 1 1 d . . . H34A H 0.7728 0.0516 0.3289 0.050 Uiso 1 1 calc R . . H34B H 0.9111 0.0703 0.3400 0.050 Uiso 1 1 calc R . . H34C H 0.8692 -0.0195 0.3202 0.050 Uiso 1 1 calc R . . C35 C 1.3925(3) -0.0297(2) 0.29018(16) 0.0461(8) Uani 1 1 d . . . H35A H 1.3669 0.0100 0.3230 0.055 Uiso 1 1 calc R . . H35B H 1.3492 -0.0815 0.2971 0.055 Uiso 1 1 calc R . . C36 C 1.5557(3) -0.0706(2) 0.35148(16) 0.0448(8) Uani 1 1 d . . . H36A H 1.5381 -0.0300 0.3844 0.067 Uiso 1 1 calc R . . H36B H 1.6418 -0.0801 0.3497 0.067 Uiso 1 1 calc R . . H36C H 1.5150 -0.1218 0.3617 0.067 Uiso 1 1 calc R . . C100 C 0.6197(4) 0.0148(3) 0.0100(3) 0.0875(16) Uani 1 1 d . . . H10A H 0.6643 0.0397 0.0451 0.131 Uiso 1 1 calc R . . H10B H 0.6754 -0.0108 -0.0199 0.131 Uiso 1 1 calc R . . H10C H 0.5654 -0.0266 0.0270 0.131 Uiso 1 1 calc R . . C101 C 0.1115(3) 0.3018(2) 0.15183(16) 0.0495(8) Uani 1 1 d . . . H10D H 0.1520 0.3109 0.1926 0.074 Uiso 1 1 calc R . . H10E H 0.1016 0.2431 0.1448 0.074 Uiso 1 1 calc R . . H10F H 0.0332 0.3281 0.1527 0.074 Uiso 1 1 calc 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 S1 0.0269(3) 0.0273(3) 0.0296(3) 0.0019(3) -0.0031(3) 0.0002(3) O1 0.0396(11) 0.0345(10) 0.0301(10) 0.0020(8) 0.0015(9) -0.0018(9) O2 0.0367(11) 0.0271(9) 0.0412(11) 0.0004(8) -0.0072(9) 0.0026(8) O3 0.0282(10) 0.0356(10) 0.0292(9) 0.0045(8) 0.0000(8) 0.0042(9) O4 0.0298(12) 0.108(2) 0.0567(15) 0.0388(15) 0.0048(11) 0.0157(13) O100 0.0311(11) 0.0447(13) 0.0713(17) 0.0050(11) 0.0086(11) 0.0034(10) O101 0.0393(12) 0.0444(12) 0.0446(12) 0.0016(10) 0.0029(10) 0.0063(10) N1 0.0195(10) 0.0371(12) 0.0298(11) -0.0028(10) -0.0005(9) 0.0004(10) N2 0.0249(11) 0.0300(11) 0.0323(11) -0.0010(9) -0.0022(9) -0.0008(10) N3 0.0530(17) 0.0336(13) 0.0541(16) 0.0005(12) 0.0175(14) -0.0103(13) N4 0.0259(11) 0.0298(11) 0.0352(12) 0.0050(10) -0.0011(10) 0.0032(10) N5 0.0245(11) 0.0341(12) 0.0394(13) 0.0046(10) 0.0013(10) 0.0051(10) C1 0.0231(12) 0.0295(13) 0.0265(13) 0.0001(10) -0.0024(11) -0.0019(11) C2 0.0294(14) 0.0326(14) 0.0319(14) -0.0029(11) -0.0026(12) 0.0066(12) C3 0.0276(13) 0.0439(16) 0.0338(15) -0.0056(12) 0.0043(12) 0.0032(13) C4 0.0300(14) 0.0403(15) 0.0326(14) -0.0021(12) 0.0050(12) -0.0009(13) C5 0.0296(14) 0.0335(14) 0.0259(13) -0.0017(11) 0.0024(11) -0.0012(12) C6 0.0420(16) 0.0323(14) 0.0312(14) -0.0014(11) 0.0056(13) -0.0027(13) C7 0.0482(18) 0.0270(13) 0.0412(16) -0.0025(12) 0.0074(15) 0.0009(13) C8 0.0349(15) 0.0358(15) 0.0399(16) -0.0022(12) 0.0082(13) 0.0062(13) C9 0.0276(14) 0.0321(14) 0.0354(15) -0.0007(11) 0.0011(11) 0.0003(12) C10 0.0243(13) 0.0302(13) 0.0233(12) -0.0025(10) -0.0019(10) -0.0009(11) C11 0.0229(12) 0.0279(13) 0.0358(14) 0.0026(11) -0.0007(11) 0.0027(11) C12 0.0209(13) 0.0346(14) 0.0377(15) 0.0020(12) 0.0000(12) 0.0025(11) C13 0.0228(12) 0.0285(13) 0.0339(14) 0.0028(11) 0.0019(11) 0.0000(11) C14 0.0219(12) 0.0318(13) 0.0310(13) 0.0046(12) 0.0002(10) -0.0002(12) C15 0.0263(13) 0.0337(14) 0.0292(13) 0.0041(11) -0.0003(11) 0.0045(11) C16 0.0230(12) 0.0319(13) 0.0256(13) 0.0039(11) -0.0006(10) 0.0033(11) C17 0.0235(13) 0.0315(14) 0.0415(16) 0.0021(12) -0.0018(12) 0.0028(12) C18 0.0248(13) 0.0300(14) 0.0422(16) 0.0018(12) -0.0015(12) 0.0021(12) C19 0.0259(13) 0.0299(13) 0.0295(14) 0.0065(11) -0.0019(11) 0.0047(12) C20 0.0271(13) 0.0295(13) 0.0273(13) 0.0070(11) -0.0026(11) 0.0016(11) C21 0.0277(14) 0.0387(15) 0.0344(15) 0.0076(12) -0.0056(12) 0.0003(12) C22 0.0432(17) 0.0380(16) 0.0403(16) -0.0037(13) -0.0053(14) -0.0041(14) C23 0.0502(18) 0.0342(16) 0.0479(18) -0.0080(14) -0.0023(16) 0.0075(15) C24 0.0349(15) 0.0334(14) 0.0455(17) -0.0019(13) -0.0045(14) 0.0078(13) C25 0.0266(13) 0.0298(13) 0.0300(13) 0.0042(11) -0.0005(11) 0.0023(11) C26 0.0323(15) 0.0409(16) 0.0363(15) -0.0015(12) -0.0005(13) 0.0022(13) C27 0.046(2) 0.077(3) 0.053(2) -0.0088(19) 0.0042(17) 0.019(2) C28 0.0386(17) 0.0526(19) 0.063(2) -0.0004(17) 0.0062(17) 0.0147(16) C29 0.0238(14) 0.0392(16) 0.0465(17) 0.0112(14) 0.0042(13) 0.0050(12) C30 0.051(2) 0.067(2) 0.061(2) -0.014(2) 0.0143(19) -0.0267(19) C31 0.085(3) 0.0342(16) 0.092(3) 0.0008(17) 0.040(3) -0.010(2) C32 0.0262(14) 0.0581(19) 0.0363(16) -0.0021(14) 0.0002(13) 0.0007(14) C33 0.0270(15) 0.0351(15) 0.066(2) -0.0037(15) -0.0019(15) -0.0047(13) C34 0.0363(16) 0.0382(16) 0.0500(18) 0.0141(14) 0.0035(14) -0.0004(14) C35 0.0265(14) 0.059(2) 0.0525(19) 0.0225(16) 0.0049(14) 0.0066(15) C36 0.0357(16) 0.0517(19) 0.0471(18) 0.0066(15) -0.0051(14) 0.0082(15) C100 0.058(3) 0.100(3) 0.104(4) 0.051(3) 0.018(3) 0.027(3) C101 0.0418(17) 0.0512(19) 0.056(2) 0.0054(16) 0.0066(16) 0.0008(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.432(2) . ? S1 O2 1.4337(19) . ? S1 N1 1.638(2) . ? S1 C1 1.774(3) . ? O3 C16 1.438(3) . ? O3 H3O 0.8400 . ? O4 C36 1.371(4) . ? O4 C35 1.415(4) . ? O100 C100 1.383(4) . ? O100 H100 0.8400 . ? O101 C101 1.407(4) . ? O101 H101 0.8400 . ? N1 N2 1.393(3) . ? N1 H1 0.8800 . ? N2 C11 1.294(3) . ? N3 C6 1.417(4) . ? N3 C31 1.458(5) . ? N3 C30 1.463(5) . ? N4 C19 1.291(3) . ? N4 N5 1.410(3) . ? N5 C29 1.482(3) . ? N5 C26 1.489(4) . ? C1 C2 1.367(4) . ? C1 C10 1.434(4) . ? C2 C3 1.402(4) . ? C2 H2 0.9500 . ? C3 C4 1.369(4) . ? C3 H3 0.9500 . ? C4 C5 1.414(4) . ? C4 H4 0.9500 . ? C5 C10 1.429(4) . ? C5 C6 1.444(4) . ? C6 C7 1.366(4) . ? C7 C8 1.404(4) . ? C7 H7 0.9500 . ? C8 C9 1.371(4) . ? C8 H8 0.9500 . ? C9 C10 1.418(4) . ? C9 H9 0.9500 . ? C11 C12 1.440(4) . ? C11 H11 0.9500 . ? C12 C13 1.346(4) . ? C12 H12 0.9500 . ? C13 C14 1.462(4) . ? C13 C32 1.501(4) . ? C14 C15 1.329(4) . ? C14 H14 0.9500 . ? C15 C16 1.515(4) . ? C15 H15 0.9500 . ? C16 C25 1.519(4) . ? C16 C17 1.565(4) . ? C17 C33 1.527(4) . ? C17 C18 1.534(4) . ? C17 C34 1.542(4) . ? C18 C19 1.496(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.488(4) . ? C20 C21 1.401(4) . ? C20 C25 1.405(4) . ? C21 C22 1.381(4) . ? C21 H21 0.9500 . ? C22 C23 1.391(4) . ? C22 H22 0.9500 . ? C23 C24 1.378(4) . ? C23 H23 0.9500 . ? C24 C25 1.401(4) . ? C24 H24 0.9500 . ? C26 C27 1.503(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.510(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.522(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C35 1.494(4) . ? C29 H29 1.0000 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? C101 H10D 0.9800 . ? C101 H10E 0.9800 . ? C101 H10F 0.9800 . ? 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 _geom_angle_publ_flag O1 S1 O2 119.18(12) . . ? O1 S1 N1 104.64(12) . . ? O2 S1 N1 107.32(12) . . ? O1 S1 C1 110.28(12) . . ? O2 S1 C1 107.23(12) . . ? N1 S1 C1 107.65(12) . . ? C16 O3 H3O 109.5 . . ? C36 O4 C35 114.2(3) . . ? C100 O100 H100 109.5 . . ? C101 O101 H101 109.5 . . ? N2 N1 S1 114.79(16) . . ? N2 N1 H1 122.6 . . ? S1 N1 H1 122.6 . . ? C11 N2 N1 114.8(2) . . ? C6 N3 C31 115.2(3) . . ? C6 N3 C30 115.4(3) . . ? C31 N3 C30 111.1(3) . . ? C19 N4 N5 116.4(2) . . ? N4 N5 C29 109.9(2) . . ? N4 N5 C26 115.1(2) . . ? C29 N5 C26 106.1(2) . . ? C2 C1 C10 121.8(2) . . ? C2 C1 S1 116.6(2) . . ? C10 C1 S1 121.7(2) . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.7(3) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C10 119.3(2) . . ? C4 C5 C6 121.4(3) . . ? C10 C5 C6 119.3(2) . . ? C7 C6 N3 123.6(3) . . ? C7 C6 C5 118.7(3) . . ? N3 C6 C5 117.7(3) . . ? C6 C7 C8 121.6(3) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C5 119.2(2) . . ? C9 C10 C1 123.9(2) . . ? C5 C10 C1 116.9(2) . . ? N2 C11 C12 118.9(2) . . ? N2 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 126.8(2) . . ? C13 C12 H12 116.6 . . ? C11 C12 H12 116.6 . . ? C12 C13 C14 122.3(2) . . ? C12 C13 C32 119.6(2) . . ? C14 C13 C32 118.1(2) . . ? C15 C14 C13 125.4(3) . . ? C15 C14 H14 117.3 . . ? C13 C14 H14 117.3 . . ? C14 C15 C16 124.5(2) . . ? C14 C15 H15 117.7 . . ? C16 C15 H15 117.7 . . ? O3 C16 C15 110.2(2) . . ? O3 C16 C25 108.9(2) . . ? C15 C16 C25 112.4(2) . . ? O3 C16 C17 105.1(2) . . ? C15 C16 C17 110.8(2) . . ? C25 C16 C17 109.1(2) . . ? C33 C17 C18 108.4(2) . . ? C33 C17 C34 108.7(2) . . ? C18 C17 C34 110.4(2) . . ? C33 C17 C16 111.4(2) . . ? C18 C17 C16 107.1(2) . . ? C34 C17 C16 110.8(2) . . ? C19 C18 C17 115.0(2) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? N4 C19 C20 116.0(2) . . ? N4 C19 C18 125.6(3) . . ? C20 C19 C18 118.4(2) . . ? C21 C20 C25 119.6(3) . . ? C21 C20 C19 120.3(2) . . ? C25 C20 C19 120.1(2) . . ? C22 C21 C20 120.8(3) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.8(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 119.8(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 121.5(3) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C24 C25 C20 118.4(3) . . ? C24 C25 C16 121.9(2) . . ? C20 C25 C16 119.7(2) . . ? N5 C26 C27 106.5(2) . . ? N5 C26 H26A 110.4 . . ? C27 C26 H26A 110.4 . . ? N5 C26 H26B 110.4 . . ? C27 C26 H26B 110.4 . . ? H26A C26 H26B 108.6 . . ? C26 C27 C28 105.4(3) . . ? C26 C27 H27A 110.7 . . ? C28 C27 H27A 110.7 . . ? C26 C27 H27B 110.7 . . ? C28 C27 H27B 110.7 . . ? H27A C27 H27B 108.8 . . ? C27 C28 C29 103.6(3) . . ? C27 C28 H28A 111.0 . . ? C29 C28 H28A 111.0 . . ? C27 C28 H28B 111.0 . . ? C29 C28 H28B 111.0 . . ? H28A C28 H28B 109.0 . . ? N5 C29 C35 111.3(2) . . ? N5 C29 C28 101.8(3) . . ? C35 C29 C28 114.1(3) . . ? N5 C29 H29 109.8 . . ? C35 C29 H29 109.8 . . ? C28 C29 H29 109.8 . . ? N3 C30 H30A 109.5 . . ? N3 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N3 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N3 C31 H31A 109.5 . . ? N3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C13 C32 H32A 109.5 . . ? C13 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C13 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C17 C33 H33A 109.5 . . ? C17 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C17 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C17 C34 H34A 109.5 . . ? C17 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C17 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O4 C35 C29 106.3(3) . . ? O4 C35 H35A 110.5 . . ? C29 C35 H35A 110.5 . . ? O4 C35 H35B 110.5 . . ? C29 C35 H35B 110.5 . . ? H35A C35 H35B 108.7 . . ? O4 C36 H36A 109.5 . . ? O4 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O4 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O100 C100 H10A 109.5 . . ? O100 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O100 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? O101 C101 H10D 109.5 . . ? O101 C101 H10E 109.5 . . ? H10D C101 H10E 109.5 . . ? O101 C101 H10F 109.5 . . ? H10D C101 H10F 109.5 . . ? H10E C101 H10F 109.5 . . ? 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 O1 S1 N1 N2 176.67(18) . . . . ? O2 S1 N1 N2 49.1(2) . . . . ? C1 S1 N1 N2 -66.0(2) . . . . ? S1 N1 N2 C11 174.15(19) . . . . ? C19 N4 N5 C29 -173.0(2) . . . . ? C19 N4 N5 C26 67.2(3) . . . . ? O1 S1 C1 C2 -139.4(2) . . . . ? O2 S1 C1 C2 -8.2(2) . . . . ? N1 S1 C1 C2 107.0(2) . . . . ? O1 S1 C1 C10 40.8(3) . . . . ? O2 S1 C1 C10 172.0(2) . . . . ? N1 S1 C1 C10 -72.8(2) . . . . ? C10 C1 C2 C3 1.0(4) . . . . ? S1 C1 C2 C3 -178.8(2) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C10 3.2(4) . . . . ? C3 C4 C5 C6 -177.8(3) . . . . ? C31 N3 C6 C7 18.7(5) . . . . ? C30 N3 C6 C7 -112.9(3) . . . . ? C31 N3 C6 C5 -159.3(3) . . . . ? C30 N3 C6 C5 69.0(4) . . . . ? C4 C5 C6 C7 -173.1(3) . . . . ? C10 C5 C6 C7 5.9(4) . . . . ? C4 C5 C6 N3 5.1(4) . . . . ? C10 C5 C6 N3 -175.9(3) . . . . ? N3 C6 C7 C8 178.8(3) . . . . ? C5 C6 C7 C8 -3.2(5) . . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C7 C8 C9 C10 2.4(4) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? C8 C9 C10 C1 178.6(3) . . . . ? C4 C5 C10 C9 174.4(2) . . . . ? C6 C5 C10 C9 -4.6(4) . . . . ? C4 C5 C10 C1 -3.9(4) . . . . ? C6 C5 C10 C1 177.1(3) . . . . ? C2 C1 C10 C9 -176.3(3) . . . . ? S1 C1 C10 C9 3.5(4) . . . . ? C2 C1 C10 C5 1.9(4) . . . . ? S1 C1 C10 C5 -178.29(19) . . . . ? N1 N2 C11 C12 -178.5(2) . . . . ? N2 C11 C12 C13 -177.9(3) . . . . ? C11 C12 C13 C14 4.5(4) . . . . ? C11 C12 C13 C32 -174.4(3) . . . . ? C12 C13 C14 C15 -171.9(3) . . . . ? C32 C13 C14 C15 7.1(4) . . . . ? C13 C14 C15 C16 179.9(2) . . . . ? C14 C15 C16 O3 11.0(4) . . . . ? C14 C15 C16 C25 132.8(3) . . . . ? C14 C15 C16 C17 -104.8(3) . . . . ? O3 C16 C17 C33 -63.2(3) . . . . ? C15 C16 C17 C33 55.8(3) . . . . ? C25 C16 C17 C33 -179.9(2) . . . . ? O3 C16 C17 C18 55.1(3) . . . . ? C15 C16 C17 C18 174.1(2) . . . . ? C25 C16 C17 C18 -61.6(3) . . . . ? O3 C16 C17 C34 175.6(2) . . . . ? C15 C16 C17 C34 -65.3(3) . . . . ? C25 C16 C17 C34 58.9(3) . . . . ? C33 C17 C18 C19 171.5(2) . . . . ? C34 C17 C18 C19 -69.6(3) . . . . ? C16 C17 C18 C19 51.2(3) . . . . ? N5 N4 C19 C20 -177.5(2) . . . . ? N5 N4 C19 C18 4.3(4) . . . . ? C17 C18 C19 N4 163.3(3) . . . . ? C17 C18 C19 C20 -14.8(4) . . . . ? N4 C19 C20 C21 -11.2(4) . . . . ? C18 C19 C20 C21 167.2(2) . . . . ? N4 C19 C20 C25 168.7(2) . . . . ? C18 C19 C20 C25 -12.9(4) . . . . ? C25 C20 C21 C22 -0.7(4) . . . . ? C19 C20 C21 C22 179.2(3) . . . . ? C20 C21 C22 C23 -0.7(4) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C22 C23 C24 C25 1.8(5) . . . . ? C23 C24 C25 C20 -3.2(4) . . . . ? C23 C24 C25 C16 179.4(3) . . . . ? C21 C20 C25 C24 2.6(4) . . . . ? C19 C20 C25 C24 -177.3(2) . . . . ? C21 C20 C25 C16 -179.9(2) . . . . ? C19 C20 C25 C16 0.1(4) . . . . ? O3 C16 C25 C24 100.9(3) . . . . ? C15 C16 C25 C24 -21.6(4) . . . . ? C17 C16 C25 C24 -144.9(3) . . . . ? O3 C16 C25 C20 -76.5(3) . . . . ? C15 C16 C25 C20 161.1(2) . . . . ? C17 C16 C25 C20 37.8(3) . . . . ? N4 N5 C26 C27 142.1(3) . . . . ? C29 N5 C26 C27 20.3(3) . . . . ? N5 C26 C27 C28 5.3(4) . . . . ? C26 C27 C28 C29 -28.1(4) . . . . ? N4 N5 C29 C35 75.7(3) . . . . ? C26 N5 C29 C35 -159.2(3) . . . . ? N4 N5 C29 C28 -162.4(2) . . . . ? C26 N5 C29 C28 -37.3(3) . . . . ? C27 C28 C29 N5 40.1(3) . . . . ? C27 C28 C29 C35 160.1(3) . . . . ? C36 O4 C35 C29 178.3(3) . . . . ? N5 C29 C35 O4 177.5(3) . . . . ? C28 C29 C35 O4 63.0(4) . . . . ? 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 N1 H1 O100 0.88 2.03 2.782(3) 143.0 . O3 H3O O1 0.84 2.17 2.984(3) 163.9 3 O101 H101 N2 0.84 2.10 2.941(3) 174.7 . O101 H101 O2 0.84 2.66 3.065(3) 111.1 . O3 H3O O1 0.84 2.17 2.984(3) 163.9 3 O100 H100 O101 0.84 1.82 2.656(3) 172.2 3 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.460 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.045