# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cu_szia_104e_0m _database_code_depnum_ccdc_archive 'CCDC 882511' #TrackingRef 'Neoadenoloside B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H38 O12, C5 H5 N' _chemical_formula_sum 'C33 H43 N O12' _chemical_formula_weight 645.68 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_space_group_name_Hall 'P 4abw 2nw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' '-x+1/2, y+1/2, -z+1/4' '-x, -y, z+1/2' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.6541(2) _cell_length_b 11.6541(2) _cell_length_c 43.9234(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5965.59(18) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9827 _cell_measurement_theta_min 3.92 _cell_measurement_theta_max 68.92 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 0.914 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 44905 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 69.69 _reflns_number_total 5504 _reflns_number_gt 5493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0343P)^2^+2.0351P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00022(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(11) _refine_ls_number_reflns 5504 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _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 O1 O 0.38755(9) 1.15187(9) 0.03110(2) 0.0210(2) Uani 1 1 d . . . O1'' O 0.26876(9) 1.05769(9) -0.00051(2) 0.0246(2) Uani 1 1 d . . . O6 O 0.88157(9) 1.10048(9) 0.00432(2) 0.0200(2) Uani 1 1 d . . . H6 H 0.9487 1.1266 0.0034 0.030 Uiso 1 1 calc R . . O20 O 0.71360(8) 1.26349(8) 0.05946(2) 0.0191(2) Uani 1 1 d . . . O14 O 0.84234(9) 0.90537(8) 0.03598(2) 0.0209(2) Uani 1 1 d . . . H14 H 0.8644 0.9605 0.0251 0.031 Uiso 1 1 calc R . . O15 O 0.60603(9) 0.70043(9) 0.12177(2) 0.0233(2) Uani 1 1 d . . . O4' O 0.66916(9) 0.56311(9) 0.09107(2) 0.0236(2) Uani 1 1 d . . . O6' O 0.99488(9) 0.56205(9) 0.05317(2) 0.0245(2) Uani 1 1 d . . . O2' O 1.00334(9) 0.75381(9) 0.05804(2) 0.0226(2) Uani 1 1 d . . . H2' H 0.9605 0.7952 0.0473 0.034 Uiso 1 1 calc R . . O5' O 0.89793(9) 0.54554(8) 0.11271(2) 0.0212(2) Uani 1 1 d . . . O3' O 0.78158(10) 0.68171(9) 0.03119(2) 0.0234(2) Uani 1 1 d . . . H3' H 0.7930 0.7509 0.0268 0.035 Uiso 1 1 calc R . . O7 O 0.89385(8) 1.18693(8) 0.06481(2) 0.0197(2) Uani 1 1 d . . . H7 H 0.8859 1.1804 0.0837 0.030 Uiso 1 1 calc R . . N1S N 0.25187(16) 1.03241(15) 0.12288(4) 0.0439(4) Uani 1 1 d . . . C1S C 0.31789(17) 0.93918(18) 0.12529(4) 0.0397(4) Uani 1 1 d . . . H1S H 0.3951 0.9439 0.1185 0.048 Uiso 1 1 calc R . . C2S C 0.27997(17) 0.83676(18) 0.13711(5) 0.0427(4) Uani 1 1 d . . . H2S H 0.3302 0.7727 0.1385 0.051 Uiso 1 1 calc R . . C3S C 0.16776(17) 0.82836(16) 0.14701(4) 0.0395(4) Uani 1 1 d . . . H3S H 0.1394 0.7589 0.1555 0.047 Uiso 1 1 calc R . . C4S C 0.09843(16) 0.92257(16) 0.14434(4) 0.0354(4) Uani 1 1 d . . . H4S H 0.0206 0.9196 0.1508 0.042 Uiso 1 1 calc R . . C5S C 0.14325(18) 1.02154(18) 0.13225(4) 0.0413(4) Uani 1 1 d . . . H5S H 0.0941 1.0862 0.1304 0.050 Uiso 1 1 calc R . . C6' C 0.95537(14) 0.45452(13) 0.06564(3) 0.0243(3) Uani 1 1 d . . . H6'1 H 1.0191 0.4155 0.0764 0.029 Uiso 1 1 calc R . . H6'2 H 0.9286 0.4038 0.0490 0.029 Uiso 1 1 calc R . . C5' C 0.85809(14) 0.47728(12) 0.08765(3) 0.0223(3) Uani 1 1 d . . . H5' H 0.8265 0.4030 0.0953 0.027 Uiso 1 1 calc R . . C4' C 0.76540(13) 0.54330(13) 0.07101(3) 0.0208(3) Uani 1 1 d . . . H4' H 0.7400 0.4998 0.0526 0.025 Uiso 1 1 calc R . . C3' C 0.81270(13) 0.66216(12) 0.06168(3) 0.0184(3) Uani 1 1 d . . . C16 C 0.76426(12) 0.74289(12) 0.08694(3) 0.0172(3) Uani 1 1 d . . . C13 C 0.71135(12) 0.86041(12) 0.07821(3) 0.0172(3) Uani 1 1 d . . . H13 H 0.6862 0.8952 0.0979 0.021 Uiso 1 1 calc R . . C14 C 0.79507(12) 0.94899(12) 0.06413(3) 0.0175(3) Uani 1 1 d . . . H14A H 0.8589 0.9643 0.0788 0.021 Uiso 1 1 calc R . . C8 C 0.72687(12) 1.05852(12) 0.05929(3) 0.0168(3) Uani 1 1 d . . . H8 H 0.6888 1.0746 0.0792 0.020 Uiso 1 1 calc R . . C9 C 0.62821(12) 1.03889(12) 0.03644(3) 0.0168(3) Uani 1 1 d . . . H9 H 0.6610 0.9945 0.0190 0.020 Uiso 1 1 calc R . . C10 C 0.59303(12) 1.15788(12) 0.02374(3) 0.0180(3) Uani 1 1 d . . . C1 C 0.47724(12) 1.15518(13) 0.00749(3) 0.0197(3) Uani 1 1 d . . . H1 H 0.4722 1.0843 -0.0053 0.024 Uiso 1 1 calc R . . C1'' C 0.28783(13) 1.10195(13) 0.02392(3) 0.0214(3) Uani 1 1 d . . . C2'' C 0.20324(14) 1.10760(15) 0.04949(4) 0.0287(3) Uani 1 1 d . . . H2'1 H 0.1661 1.1830 0.0496 0.043 Uiso 1 1 calc R . . H2'2 H 0.2431 1.0957 0.0689 0.043 Uiso 1 1 calc R . . H2'3 H 0.1451 1.0477 0.0468 0.043 Uiso 1 1 calc R . . C2 C 0.45650(14) 1.25958(13) -0.01238(3) 0.0243(3) Uani 1 1 d . . . H2A H 0.4520 1.3287 0.0007 0.029 Uiso 1 1 calc R . . H2B H 0.3820 1.2510 -0.0230 0.029 Uiso 1 1 calc R . . C3 C 0.55121(14) 1.27589(13) -0.03589(3) 0.0244(3) Uani 1 1 d . . . H3A H 0.5334 1.3441 -0.0485 0.029 Uiso 1 1 calc R . . H3B H 0.5531 1.2082 -0.0495 0.029 Uiso 1 1 calc R . . C4 C 0.66954(13) 1.29154(12) -0.02137(3) 0.0213(3) Uani 1 1 d . . . C5 C 0.68922(12) 1.18658(12) 0.00007(3) 0.0183(3) Uani 1 1 d . . . H5 H 0.6920 1.1186 -0.0138 0.022 Uiso 1 1 calc R . . C6 C 0.80591(12) 1.18695(12) 0.01650(3) 0.0183(3) Uani 1 1 d . . . H6A H 0.8424 1.2636 0.0132 0.022 Uiso 1 1 calc R . . C7 C 0.78897(12) 1.16996(12) 0.05067(3) 0.0176(3) Uani 1 1 d . . . C20 C 0.59635(12) 1.24232(12) 0.05068(3) 0.0188(3) Uani 1 1 d . . . H20A H 0.5592 1.3154 0.0448 0.023 Uiso 1 1 calc R . . H20B H 0.5535 1.2098 0.0681 0.023 Uiso 1 1 calc R . . C15 C 0.67159(12) 0.67031(12) 0.10199(3) 0.0182(3) Uani 1 1 d . . . C2' C 0.94347(13) 0.65798(12) 0.06750(3) 0.0203(3) Uani 1 1 d . . . C1' C 0.94519(12) 0.65369(12) 0.10235(3) 0.0192(3) Uani 1 1 d . . . H1' H 1.0241 0.6668 0.1106 0.023 Uiso 1 1 calc R . . C17 C 0.86451(12) 0.75158(12) 0.11055(3) 0.0183(3) Uani 1 1 d . . . H17A H 0.9041 0.8265 0.1088 0.022 Uiso 1 1 calc R . . H17B H 0.8353 0.7427 0.1316 0.022 Uiso 1 1 calc R . . C12 C 0.60006(12) 0.84706(12) 0.05926(3) 0.0202(3) Uani 1 1 d . . . H12A H 0.6189 0.8077 0.0399 0.024 Uiso 1 1 calc R . . H12B H 0.5459 0.7976 0.0706 0.024 Uiso 1 1 calc R . . C11 C 0.54066(12) 0.96099(12) 0.05195(3) 0.0199(3) Uani 1 1 d . . . H11A H 0.4744 0.9477 0.0383 0.024 Uiso 1 1 calc R . . H11B H 0.5124 0.9972 0.0709 0.024 Uiso 1 1 calc R . . C18 C 0.76004(14) 1.28650(13) -0.04670(3) 0.0247(3) Uani 1 1 d . . . H18A H 0.7549 1.2125 -0.0572 0.037 Uiso 1 1 calc R . . H18B H 0.8367 1.2951 -0.0378 0.037 Uiso 1 1 calc R . . H18C H 0.7463 1.3487 -0.0613 0.037 Uiso 1 1 calc R . . C19 C 0.67840(14) 1.40980(13) -0.00608(3) 0.0254(3) Uani 1 1 d . . . H19A H 0.6652 1.4699 -0.0213 0.038 Uiso 1 1 calc R . . H19B H 0.7551 1.4191 0.0027 0.038 Uiso 1 1 calc R . . H19C H 0.6206 1.4158 0.0100 0.038 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 O1 0.0185(5) 0.0239(5) 0.0205(5) -0.0019(4) -0.0013(4) 0.0027(4) O1'' 0.0253(6) 0.0231(5) 0.0253(5) -0.0034(4) -0.0038(4) -0.0002(4) O6 0.0203(5) 0.0189(5) 0.0207(5) 0.0008(4) 0.0041(4) -0.0004(4) O20 0.0204(5) 0.0166(5) 0.0204(5) -0.0042(4) -0.0002(4) 0.0002(4) O14 0.0248(5) 0.0172(5) 0.0206(5) 0.0023(4) 0.0060(4) 0.0002(4) O15 0.0230(5) 0.0273(5) 0.0196(5) 0.0034(4) 0.0034(4) -0.0003(4) O4' 0.0231(5) 0.0198(5) 0.0280(5) -0.0006(4) 0.0025(4) -0.0058(4) O6' 0.0277(6) 0.0186(5) 0.0270(5) 0.0001(4) 0.0081(4) 0.0023(4) O2' 0.0207(5) 0.0198(5) 0.0275(5) 0.0048(4) 0.0037(4) -0.0014(4) O5' 0.0282(6) 0.0163(5) 0.0191(5) 0.0012(4) -0.0004(4) -0.0016(4) O3' 0.0334(6) 0.0225(5) 0.0144(5) 0.0007(4) -0.0027(4) 0.0002(4) O7 0.0194(5) 0.0219(5) 0.0178(5) -0.0002(4) -0.0009(4) -0.0040(4) N1S 0.0487(10) 0.0447(10) 0.0384(8) 0.0141(7) -0.0032(7) -0.0039(8) C1S 0.0348(10) 0.0533(12) 0.0309(9) 0.0048(8) -0.0009(8) -0.0053(9) C2S 0.0410(11) 0.0364(10) 0.0509(11) -0.0021(9) -0.0022(9) 0.0022(8) C3S 0.0405(10) 0.0305(9) 0.0477(11) 0.0000(8) -0.0032(8) -0.0108(8) C4S 0.0322(9) 0.0456(11) 0.0283(8) -0.0035(7) -0.0052(7) -0.0043(8) C5S 0.0450(11) 0.0435(11) 0.0353(9) 0.0053(8) -0.0058(8) 0.0069(9) C6' 0.0325(8) 0.0164(7) 0.0241(8) -0.0003(6) 0.0021(6) 0.0015(6) C5' 0.0299(8) 0.0149(7) 0.0222(7) -0.0007(6) 0.0001(6) -0.0019(6) C4' 0.0229(7) 0.0184(7) 0.0212(7) -0.0032(6) 0.0022(6) -0.0033(6) C3' 0.0242(7) 0.0165(7) 0.0145(6) -0.0001(5) -0.0001(5) -0.0017(6) C16 0.0191(7) 0.0168(7) 0.0156(6) -0.0004(5) 0.0003(5) -0.0012(5) C13 0.0176(7) 0.0166(7) 0.0174(6) 0.0001(5) 0.0006(5) -0.0008(5) C14 0.0168(6) 0.0180(7) 0.0176(6) 0.0009(5) -0.0001(5) -0.0025(5) C8 0.0171(7) 0.0183(7) 0.0149(6) -0.0006(5) 0.0018(5) -0.0013(5) C9 0.0171(7) 0.0167(7) 0.0168(6) -0.0020(5) -0.0004(5) 0.0005(5) C10 0.0203(7) 0.0168(7) 0.0168(6) -0.0014(5) -0.0001(6) 0.0003(5) C1 0.0203(7) 0.0200(7) 0.0189(7) -0.0014(6) -0.0009(5) 0.0023(5) C1'' 0.0204(7) 0.0198(7) 0.0241(7) 0.0022(6) -0.0042(6) 0.0041(6) C2'' 0.0224(8) 0.0372(9) 0.0265(8) -0.0012(7) -0.0007(6) 0.0006(7) C2 0.0242(8) 0.0213(8) 0.0274(8) 0.0005(6) -0.0056(6) 0.0044(6) C3 0.0325(8) 0.0200(7) 0.0206(7) 0.0039(6) -0.0053(6) 0.0013(6) C4 0.0287(8) 0.0158(7) 0.0195(7) 0.0017(6) -0.0019(6) -0.0002(6) C5 0.0232(7) 0.0149(7) 0.0170(6) -0.0020(5) 0.0008(5) -0.0001(5) C6 0.0217(7) 0.0144(7) 0.0189(7) 0.0008(5) 0.0032(6) -0.0008(5) C7 0.0183(7) 0.0154(7) 0.0190(7) -0.0013(5) -0.0006(5) 0.0006(5) C20 0.0189(7) 0.0186(7) 0.0190(7) -0.0019(6) 0.0000(5) 0.0029(6) C15 0.0181(7) 0.0187(7) 0.0178(7) 0.0028(5) -0.0024(5) 0.0001(5) C2' 0.0226(7) 0.0167(7) 0.0217(7) 0.0003(6) 0.0030(6) -0.0007(6) C1' 0.0191(7) 0.0173(7) 0.0211(7) 0.0012(6) -0.0022(5) -0.0018(6) C17 0.0196(7) 0.0176(7) 0.0177(6) 0.0008(5) -0.0023(5) -0.0022(5) C12 0.0186(7) 0.0185(7) 0.0234(7) 0.0014(6) -0.0020(6) -0.0034(6) C11 0.0181(7) 0.0214(7) 0.0201(7) 0.0020(5) -0.0018(5) -0.0019(6) C18 0.0346(9) 0.0197(7) 0.0197(7) 0.0019(6) 0.0014(6) -0.0026(6) C19 0.0327(9) 0.0184(7) 0.0251(7) 0.0015(6) -0.0002(6) 0.0007(6) _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 O1 C1'' 1.3373(19) . ? O1 C1 1.4728(17) . ? O1'' C1'' 1.2112(18) . ? O6 C6 1.4418(17) . ? O6 H6 0.8400 . ? O20 C20 1.4410(17) . ? O20 C7 1.4523(17) . ? O14 C14 1.4459(17) . ? O14 H14 0.8400 . ? O15 C15 1.2091(18) . ? O4' C15 1.3386(17) . ? O4' C4' 1.4450(18) . ? O6' C2' 1.4160(17) . ? O6' C6' 1.4431(18) . ? O2' C2' 1.3810(18) . ? O2' H2' 0.8400 . ? O5' C5' 1.4354(18) . ? O5' C1' 1.4488(17) . ? O3' C3' 1.4059(16) . ? O3' H3' 0.8400 . ? O7 C7 1.3853(17) . ? O7 H7 0.8400 . ? N1S C1S 1.336(3) . ? N1S C5S 1.337(3) . ? C1S C2S 1.375(3) . ? C1S H1S 0.9500 . ? C2S C3S 1.382(3) . ? C2S H2S 0.9500 . ? C3S C4S 1.368(3) . ? C3S H3S 0.9500 . ? C4S C5S 1.373(3) . ? C4S H4S 0.9500 . ? C5S H5S 0.9500 . ? C6' C5' 1.513(2) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C5' C4' 1.514(2) . ? C5' H5' 1.0000 . ? C4' C3' 1.546(2) . ? C4' H4' 1.0000 . ? C3' C2' 1.546(2) . ? C3' C16 1.5604(19) . ? C16 C15 1.5228(19) . ? C16 C13 1.5501(19) . ? C16 C17 1.5654(18) . ? C13 C12 1.5489(19) . ? C13 C14 1.5492(19) . ? C13 H13 1.0000 . ? C14 C8 1.519(2) . ? C14 H14A 1.0000 . ? C8 C7 1.5343(19) . ? C8 C9 1.5433(18) . ? C8 H8 1.0000 . ? C9 C11 1.5261(19) . ? C9 C10 1.5499(19) . ? C9 H9 1.0000 . ? C10 C1 1.5269(19) . ? C10 C20 1.5396(19) . ? C10 C5 1.5650(19) . ? C1 C2 1.517(2) . ? C1 H1 1.0000 . ? C1'' C2'' 1.496(2) . ? C2'' H2'1 0.9800 . ? C2'' H2'2 0.9800 . ? C2'' H2'3 0.9800 . ? C2 C3 1.523(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.530(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C18 1.534(2) . ? C4 C19 1.536(2) . ? C4 C5 1.5607(19) . ? C5 C6 1.539(2) . ? C5 H5 1.0000 . ? C6 C7 1.5267(19) . ? C6 H6A 1.0000 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C2' C1' 1.5314(19) . ? C1' C17 1.522(2) . ? C1' H1' 1.0000 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C12 C11 1.531(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C1'' O1 C1 117.53(11) . . ? C6 O6 H6 109.5 . . ? C20 O20 C7 111.95(10) . . ? C14 O14 H14 109.5 . . ? C15 O4' C4' 110.56(11) . . ? C2' O6' C6' 112.45(11) . . ? C2' O2' H2' 109.5 . . ? C5' O5' C1' 111.35(10) . . ? C3' O3' H3' 109.5 . . ? C7 O7 H7 109.5 . . ? C1S N1S C5S 116.35(18) . . ? N1S C1S C2S 123.44(18) . . ? N1S C1S H1S 118.3 . . ? C2S C1S H1S 118.3 . . ? C1S C2S C3S 119.00(19) . . ? C1S C2S H2S 120.5 . . ? C3S C2S H2S 120.5 . . ? C4S C3S C2S 118.37(18) . . ? C4S C3S H3S 120.8 . . ? C2S C3S H3S 120.8 . . ? C3S C4S C5S 118.85(18) . . ? C3S C4S H4S 120.6 . . ? C5S C4S H4S 120.6 . . ? N1S C5S C4S 123.98(19) . . ? N1S C5S H5S 118.0 . . ? C4S C5S H5S 118.0 . . ? O6' C6' C5' 109.23(12) . . ? O6' C6' H6'1 109.8 . . ? C5' C6' H6'1 109.8 . . ? O6' C6' H6'2 109.8 . . ? C5' C6' H6'2 109.8 . . ? H6'1 C6' H6'2 108.3 . . ? O5' C5' C6' 110.16(13) . . ? O5' C5' C4' 108.62(11) . . ? C6' C5' C4' 108.36(12) . . ? O5' C5' H5' 109.9 . . ? C6' C5' H5' 109.9 . . ? C4' C5' H5' 109.9 . . ? O4' C4' C5' 109.91(12) . . ? O4' C4' C3' 107.17(11) . . ? C5' C4' C3' 109.20(12) . . ? O4' C4' H4' 110.2 . . ? C5' C4' H4' 110.2 . . ? C3' C4' H4' 110.2 . . ? O3' C3' C2' 114.65(12) . . ? O3' C3' C4' 107.80(11) . . ? C2' C3' C4' 106.21(11) . . ? O3' C3' C16 119.10(12) . . ? C2' C3' C16 104.94(11) . . ? C4' C3' C16 102.87(11) . . ? C15 C16 C13 108.42(11) . . ? C15 C16 C3' 103.32(11) . . ? C13 C16 C3' 120.05(11) . . ? C15 C16 C17 106.12(11) . . ? C13 C16 C17 113.80(11) . . ? C3' C16 C17 103.89(11) . . ? C12 C13 C14 112.32(11) . . ? C12 C13 C16 112.17(11) . . ? C14 C13 C16 115.91(11) . . ? C12 C13 H13 105.1 . . ? C14 C13 H13 105.1 . . ? C16 C13 H13 105.1 . . ? O14 C14 C8 112.04(11) . . ? O14 C14 C13 110.31(11) . . ? C8 C14 C13 106.64(11) . . ? O14 C14 H14A 109.3 . . ? C8 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C14 C8 C7 119.95(11) . . ? C14 C8 C9 110.88(11) . . ? C7 C8 C9 108.45(11) . . ? C14 C8 H8 105.5 . . ? C7 C8 H8 105.5 . . ? C9 C8 H8 105.5 . . ? C11 C9 C8 107.22(11) . . ? C11 C9 C10 121.07(12) . . ? C8 C9 C10 107.36(11) . . ? C11 C9 H9 106.8 . . ? C8 C9 H9 106.8 . . ? C10 C9 H9 106.8 . . ? C1 C10 C20 113.25(12) . . ? C1 C10 C9 112.55(11) . . ? C20 C10 C9 106.78(11) . . ? C1 C10 C5 109.08(11) . . ? C20 C10 C5 110.85(11) . . ? C9 C10 C5 103.94(11) . . ? O1 C1 C2 108.24(12) . . ? O1 C1 C10 107.38(11) . . ? C2 C1 C10 113.16(12) . . ? O1 C1 H1 109.3 . . ? C2 C1 H1 109.3 . . ? C10 C1 H1 109.3 . . ? O1'' C1'' O1 123.61(14) . . ? O1'' C1'' C2'' 124.27(14) . . ? O1 C1'' C2'' 112.12(12) . . ? C1'' C2'' H2'1 109.5 . . ? C1'' C2'' H2'2 109.5 . . ? H2'1 C2'' H2'2 109.5 . . ? C1'' C2'' H2'3 109.5 . . ? H2'1 C2'' H2'3 109.5 . . ? H2'2 C2'' H2'3 109.5 . . ? C1 C2 C3 112.01(12) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 112.67(12) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C18 108.23(12) . . ? C3 C4 C19 110.46(13) . . ? C18 C4 C19 107.76(12) . . ? C3 C4 C5 106.89(12) . . ? C18 C4 C5 107.85(12) . . ? C19 C4 C5 115.44(12) . . ? C6 C5 C4 114.23(11) . . ? C6 C5 C10 108.79(11) . . ? C4 C5 C10 117.59(12) . . ? C6 C5 H5 105.0 . . ? C4 C5 H5 105.0 . . ? C10 C5 H5 105.0 . . ? O6 C6 C7 110.67(11) . . ? O6 C6 C5 111.37(11) . . ? C7 C6 C5 110.25(11) . . ? O6 C6 H6A 108.1 . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? O7 C7 O20 107.90(10) . . ? O7 C7 C6 107.96(11) . . ? O20 C7 C6 104.03(11) . . ? O7 C7 C8 115.24(11) . . ? O20 C7 C8 106.52(11) . . ? C6 C7 C8 114.42(11) . . ? O20 C20 C10 109.82(11) . . ? O20 C20 H20A 109.7 . . ? C10 C20 H20A 109.7 . . ? O20 C20 H20B 109.7 . . ? C10 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? O15 C15 O4' 121.00(13) . . ? O15 C15 C16 126.79(13) . . ? O4' C15 C16 112.20(12) . . ? O2' C2' O6' 106.91(11) . . ? O2' C2' C1' 108.70(12) . . ? O6' C2' C1' 114.40(12) . . ? O2' C2' C3' 115.01(12) . . ? O6' C2' C3' 111.61(12) . . ? C1' C2' C3' 100.33(11) . . ? O5' C1' C17 110.06(11) . . ? O5' C1' C2' 109.72(11) . . ? C17 C1' C2' 101.77(11) . . ? O5' C1' H1' 111.6 . . ? C17 C1' H1' 111.6 . . ? C2' C1' H1' 111.6 . . ? C1' C17 C16 104.82(11) . . ? C1' C17 H17A 110.8 . . ? C16 C17 H17A 110.8 . . ? C1' C17 H17B 110.8 . . ? C16 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? C11 C12 C13 113.84(12) . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C9 C11 C12 107.89(11) . . ? C9 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? C9 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C5S N1S C1S C2S -1.1(3) . . . . ? N1S C1S C2S C3S 0.2(3) . . . . ? C1S C2S C3S C4S 0.6(3) . . . . ? C2S C3S C4S C5S -0.6(3) . . . . ? C1S N1S C5S C4S 1.1(3) . . . . ? C3S C4S C5S N1S -0.3(3) . . . . ? C2' O6' C6' C5' 7.57(16) . . . . ? C1' O5' C5' C6' 58.36(14) . . . . ? C1' O5' C5' C4' -60.19(15) . . . . ? O6' C6' C5' O5' -62.67(15) . . . . ? O6' C6' C5' C4' 56.04(15) . . . . ? C15 O4' C4' C5' 100.91(13) . . . . ? C15 O4' C4' C3' -17.65(15) . . . . ? O5' C5' C4' O4' -62.32(15) . . . . ? C6' C5' C4' O4' 178.00(11) . . . . ? O5' C5' C4' C3' 54.98(15) . . . . ? C6' C5' C4' C3' -64.70(14) . . . . ? O4' C4' C3' O3' -106.90(13) . . . . ? C5' C4' C3' O3' 134.09(12) . . . . ? O4' C4' C3' C2' 129.76(12) . . . . ? C5' C4' C3' C2' 10.75(15) . . . . ? O4' C4' C3' C16 19.77(14) . . . . ? C5' C4' C3' C16 -99.24(13) . . . . ? O3' C3' C16 C15 104.20(14) . . . . ? C2' C3' C16 C15 -125.82(12) . . . . ? C4' C3' C16 C15 -14.88(14) . . . . ? O3' C3' C16 C13 -16.60(19) . . . . ? C2' C3' C16 C13 113.38(13) . . . . ? C4' C3' C16 C13 -135.68(12) . . . . ? O3' C3' C16 C17 -145.16(12) . . . . ? C2' C3' C16 C17 -15.19(14) . . . . ? C4' C3' C16 C17 95.76(12) . . . . ? C15 C16 C13 C12 -52.45(14) . . . . ? C3' C16 C13 C12 65.79(16) . . . . ? C17 C16 C13 C12 -170.27(11) . . . . ? C15 C16 C13 C14 176.73(11) . . . . ? C3' C16 C13 C14 -65.03(16) . . . . ? C17 C16 C13 C14 58.91(15) . . . . ? C12 C13 C14 O14 -69.23(14) . . . . ? C16 C13 C14 O14 61.52(15) . . . . ? C12 C13 C14 C8 52.65(14) . . . . ? C16 C13 C14 C8 -176.60(11) . . . . ? O14 C14 C8 C7 -69.56(16) . . . . ? C13 C14 C8 C7 169.66(11) . . . . ? O14 C14 C8 C9 58.07(15) . . . . ? C13 C14 C8 C9 -62.71(14) . . . . ? C14 C8 C9 C11 69.12(14) . . . . ? C7 C8 C9 C11 -157.22(11) . . . . ? C14 C8 C9 C10 -159.35(11) . . . . ? C7 C8 C9 C10 -25.69(14) . . . . ? C11 C9 C10 C1 -41.51(17) . . . . ? C8 C9 C10 C1 -164.91(11) . . . . ? C11 C9 C10 C20 83.35(15) . . . . ? C8 C9 C10 C20 -40.05(14) . . . . ? C11 C9 C10 C5 -159.40(12) . . . . ? C8 C9 C10 C5 77.20(12) . . . . ? C1'' O1 C1 C2 85.25(14) . . . . ? C1'' O1 C1 C10 -152.27(12) . . . . ? C20 C10 C1 O1 -44.59(15) . . . . ? C9 C10 C1 O1 76.64(14) . . . . ? C5 C10 C1 O1 -168.55(11) . . . . ? C20 C10 C1 C2 74.79(15) . . . . ? C9 C10 C1 C2 -163.98(12) . . . . ? C5 C10 C1 C2 -49.17(15) . . . . ? C1 O1 C1'' O1'' 1.6(2) . . . . ? C1 O1 C1'' C2'' -178.22(12) . . . . ? O1 C1 C2 C3 175.15(12) . . . . ? C10 C1 C2 C3 56.26(16) . . . . ? C1 C2 C3 C4 -59.66(17) . . . . ? C2 C3 C4 C18 170.46(12) . . . . ? C2 C3 C4 C19 -71.79(16) . . . . ? C2 C3 C4 C5 54.53(15) . . . . ? C3 C4 C5 C6 179.24(11) . . . . ? C18 C4 C5 C6 63.07(15) . . . . ? C19 C4 C5 C6 -57.47(17) . . . . ? C3 C4 C5 C10 -51.44(15) . . . . ? C18 C4 C5 C10 -167.61(12) . . . . ? C19 C4 C5 C10 71.85(17) . . . . ? C1 C10 C5 C6 -178.96(12) . . . . ? C20 C10 C5 C6 55.68(14) . . . . ? C9 C10 C5 C6 -58.70(13) . . . . ? C1 C10 C5 C4 49.21(15) . . . . ? C20 C10 C5 C4 -76.15(15) . . . . ? C9 C10 C5 C4 169.47(11) . . . . ? C4 C5 C6 O6 -108.14(13) . . . . ? C10 C5 C6 O6 118.27(12) . . . . ? C4 C5 C6 C7 128.60(12) . . . . ? C10 C5 C6 C7 -4.99(15) . . . . ? C20 O20 C7 O7 -168.93(10) . . . . ? C20 O20 C7 C6 76.57(13) . . . . ? C20 O20 C7 C8 -44.66(14) . . . . ? O6 C6 C7 O7 64.56(14) . . . . ? C5 C6 C7 O7 -171.77(11) . . . . ? O6 C6 C7 O20 179.02(10) . . . . ? C5 C6 C7 O20 -57.32(14) . . . . ? O6 C6 C7 C8 -65.18(15) . . . . ? C5 C6 C7 C8 58.49(15) . . . . ? C14 C8 C7 O7 -38.03(17) . . . . ? C9 C8 C7 O7 -166.76(11) . . . . ? C14 C8 C7 O20 -157.64(11) . . . . ? C9 C8 C7 O20 73.62(13) . . . . ? C14 C8 C7 C6 88.01(15) . . . . ? C9 C8 C7 C6 -40.73(15) . . . . ? C7 O20 C20 C10 -24.22(15) . . . . ? C1 C10 C20 O20 -164.47(11) . . . . ? C9 C10 C20 O20 71.10(14) . . . . ? C5 C10 C20 O20 -41.48(15) . . . . ? C4' O4' C15 O15 -171.76(13) . . . . ? C4' O4' C15 C16 7.60(16) . . . . ? C13 C16 C15 O15 -46.88(18) . . . . ? C3' C16 C15 O15 -175.28(13) . . . . ? C17 C16 C15 O15 75.74(17) . . . . ? C13 C16 C15 O4' 133.81(12) . . . . ? C3' C16 C15 O4' 5.41(15) . . . . ? C17 C16 C15 O4' -103.57(13) . . . . ? C6' O6' C2' O2' 168.57(12) . . . . ? C6' O6' C2' C1' 48.18(16) . . . . ? C6' O6' C2' C3' -64.87(15) . . . . ? O3' C3' C2' O2' 55.74(17) . . . . ? C4' C3' C2' O2' 174.67(11) . . . . ? C16 C3' C2' O2' -76.81(14) . . . . ? O3' C3' C2' O6' -66.27(16) . . . . ? C4' C3' C2' O6' 52.66(14) . . . . ? C16 C3' C2' O6' 161.18(11) . . . . ? O3' C3' C2' C1' 172.14(11) . . . . ? C4' C3' C2' C1' -68.93(13) . . . . ? C16 C3' C2' C1' 39.59(13) . . . . ? C5' O5' C1' C17 108.14(13) . . . . ? C5' O5' C1' C2' -3.06(15) . . . . ? O2' C2' C1' O5' -171.57(11) . . . . ? O6' C2' C1' O5' -52.18(16) . . . . ? C3' C2' C1' O5' 67.41(13) . . . . ? O2' C2' C1' C17 71.89(14) . . . . ? O6' C2' C1' C17 -168.73(12) . . . . ? C3' C2' C1' C17 -49.14(13) . . . . ? O5' C1' C17 C16 -76.01(13) . . . . ? C2' C1' C17 C16 40.29(13) . . . . ? C15 C16 C17 C1' 93.30(13) . . . . ? C13 C16 C17 C1' -147.56(11) . . . . ? C3' C16 C17 C1' -15.27(14) . . . . ? C14 C13 C12 C11 -51.20(16) . . . . ? C16 C13 C12 C11 176.17(12) . . . . ? C8 C9 C11 C12 -61.37(14) . . . . ? C10 C9 C11 C12 175.16(11) . . . . ? C13 C12 C11 C9 54.63(15) . . . . ? 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 O6 H6 O1'' 0.84 2.09 2.8438(14) 148.8 7_565 O14 H14 O6 0.84 1.88 2.7041(14) 166.2 . O2' H2' O14 0.84 1.95 2.7531(15) 160.6 . O3' H3' O14 0.84 1.93 2.7092(15) 153.4 . O7 H7 O15 0.84 1.97 2.7898(13) 165.0 5_655 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 69.69 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.220 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.035