# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email fansophia@sohu.com _publ_contact_author_name 'Fan Zhang' _publ_author_name 'Yongsheng Che ' data_sa46 _database_code_depnum_ccdc_archive 'CCDC 859983' #TrackingRef 'sa46.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C21 H30 O6), H2 O' _chemical_formula_sum 'C42 H62 O13' _chemical_formula_weight 774.92 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 56.216(11) _cell_length_b 4.9368(10) _cell_length_c 15.390(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.42(3) _cell_angle_gamma 90.00 _cell_volume 4186.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 567 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9700 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20380 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -63 _diffrn_reflns_limit_h_max 68 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.49 _reflns_number_total 7681 _reflns_number_gt 5988 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0577P)^2^+4.0316P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(15) _refine_ls_number_reflns 7681 _refine_ls_number_parameters 500 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1754 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.168 _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 0.10276(5) -0.1877(6) 0.30247(17) 0.0388(7) Uani 1 1 d . . . O1 O 0.10283(5) -0.2543(6) -0.19820(17) 0.0398(7) Uani 1 1 d . . . O1W O -0.00130(4) -0.9729(7) -0.75224(17) 0.0464(7) Uani 1 1 d . . . H1 H -0.0126 -1.0679 -0.7402 0.070 Uiso 1 1 d R . . H2 H 0.0104 -1.0609 -0.7641 0.070 Uiso 1 1 d R . . O2' O 0.10276(5) -0.5879(7) 0.15177(19) 0.0489(8) Uani 1 1 d . . . O2 O 0.10213(5) -0.6280(7) -0.35497(18) 0.0487(8) Uani 1 1 d . . . O3 O 0.06574(5) -0.5996(6) -0.44783(17) 0.0447(7) Uani 1 1 d . . . O3' O 0.06629(5) -0.5720(6) 0.05972(17) 0.0437(7) Uani 1 1 d . . . O4' O 0.03101(5) -0.0723(7) 0.13893(18) 0.0499(8) Uani 1 1 d . . . O4 O 0.03117(5) -0.1062(7) -0.35993(19) 0.0551(9) Uani 1 1 d . . . O5 O 0.01352(6) -0.6805(7) -0.60617(19) 0.0588(9) Uani 1 1 d . . . H5C H 0.0092 -0.7678 -0.6535 0.088 Uiso 1 1 calc R . . O5' O 0.01328(6) -0.6602(7) -0.10375(19) 0.0576(9) Uani 1 1 d . . . H5'C H 0.0099 -0.7555 -0.1497 0.086 Uiso 1 1 calc R . . O6 O 0.03254(6) -0.4244(7) -0.69073(19) 0.0543(8) Uani 1 1 d . . . O6' O 0.03683(6) -0.4513(7) -0.1823(2) 0.0635(9) Uani 1 1 d . . . C1 C 0.33712(8) -0.2040(13) -0.1168(3) 0.0656(16) Uani 1 1 d . . . H1A H 0.3512 -0.0942 -0.1237 0.098 Uiso 1 1 calc R . . H1B H 0.3350 -0.3523 -0.1600 0.098 Uiso 1 1 calc R . . H1C H 0.3398 -0.2790 -0.0567 0.098 Uiso 1 1 calc R . . C1' C 0.33528(9) 0.0663(15) 0.3648(4) 0.0762(18) Uani 1 1 d . . . H1'A H 0.3491 0.1902 0.3713 0.114 Uiso 1 1 calc R . . H1'B H 0.3317 -0.0051 0.3042 0.114 Uiso 1 1 calc R . . H1'C H 0.3392 -0.0838 0.4068 0.114 Uiso 1 1 calc R . . C2' C 0.31318(8) 0.2187(13) 0.3835(3) 0.0640(15) Uani 1 1 d . . . H2'A H 0.3167 0.2804 0.4460 0.077 Uiso 1 1 calc R . . H2'B H 0.3105 0.3818 0.3454 0.077 Uiso 1 1 calc R . . C2 C 0.31439(8) -0.0272(11) -0.1324(3) 0.0572(13) Uani 1 1 d . . . H2A H 0.3173 0.1320 -0.0926 0.069 Uiso 1 1 calc R . . H2B H 0.3113 0.0398 -0.1942 0.069 Uiso 1 1 calc R . . C3 C 0.29198(8) -0.1766(11) -0.1162(3) 0.0514(12) Uani 1 1 d . . . H3A H 0.2950 -0.2395 -0.0539 0.062 Uiso 1 1 calc R . . H3B H 0.2894 -0.3389 -0.1547 0.062 Uiso 1 1 calc R . . C3' C 0.29001(7) 0.0536(11) 0.3680(3) 0.0512(12) Uani 1 1 d . . . H3'A H 0.2926 -0.1073 0.4071 0.061 Uiso 1 1 calc R . . H3'B H 0.2867 -0.0118 0.3059 0.061 Uiso 1 1 calc R . . C4 C 0.26886(7) -0.0073(10) -0.1336(3) 0.0491(12) Uani 1 1 d . . . H4A H 0.2715 0.1548 -0.0950 0.059 Uiso 1 1 calc R . . H4B H 0.2659 0.0561 -0.1958 0.059 Uiso 1 1 calc R . . C4' C 0.26779(8) 0.2059(11) 0.3845(3) 0.0535(12) Uani 1 1 d . . . H4'A H 0.2654 0.3694 0.3466 0.064 Uiso 1 1 calc R . . H4'B H 0.2708 0.2667 0.4471 0.064 Uiso 1 1 calc R . . C5 C 0.24631(7) -0.1537(11) -0.1179(3) 0.0499(12) Uani 1 1 d . . . H5A H 0.2490 -0.2118 -0.0551 0.060 Uiso 1 1 calc R . . H5B H 0.2439 -0.3189 -0.1551 0.060 Uiso 1 1 calc R . . C5' C 0.24450(7) 0.0383(11) 0.3661(3) 0.0516(12) Uani 1 1 d . . . H5'A H 0.2418 -0.0278 0.3042 0.062 Uiso 1 1 calc R . . H5'B H 0.2467 -0.1220 0.4055 0.062 Uiso 1 1 calc R . . C6' C 0.22196(7) 0.1916(10) 0.3795(3) 0.0471(11) Uani 1 1 d . . . H6'A H 0.2196 0.3510 0.3397 0.057 Uiso 1 1 calc R . . H6'B H 0.2247 0.2591 0.4413 0.057 Uiso 1 1 calc R . . C6 C 0.22320(7) 0.0163(11) -0.1384(3) 0.0490(11) Uani 1 1 d . . . H6A H 0.2255 0.1806 -0.1008 0.059 Uiso 1 1 calc R . . H6B H 0.2206 0.0757 -0.2010 0.059 Uiso 1 1 calc R . . C7' C 0.19878(7) 0.0219(10) 0.3617(3) 0.0473(11) Uani 1 1 d . . . H7'A H 0.2010 -0.1358 0.4023 0.057 Uiso 1 1 calc R . . H7'B H 0.1962 -0.0483 0.3003 0.057 Uiso 1 1 calc R . . C7 C 0.20049(7) -0.1310(10) -0.1235(3) 0.0472(11) Uani 1 1 d . . . H7A H 0.1980 -0.2942 -0.1615 0.057 Uiso 1 1 calc R . . H7B H 0.2031 -0.1916 -0.0610 0.057 Uiso 1 1 calc R . . C8 C 0.17782(7) 0.0426(10) -0.1435(3) 0.0477(11) Uani 1 1 d . . . H8A H 0.1749 0.0979 -0.2066 0.057 Uiso 1 1 calc R . . H8B H 0.1805 0.2091 -0.1070 0.057 Uiso 1 1 calc R . . C8' C 0.17610(7) 0.1775(10) 0.3737(3) 0.0470(11) Uani 1 1 d . . . H8'A H 0.1790 0.2571 0.4339 0.056 Uiso 1 1 calc R . . H8'B H 0.1733 0.3285 0.3305 0.056 Uiso 1 1 calc R . . C9' C 0.15334(7) 0.0034(9) 0.3612(3) 0.0432(10) Uani 1 1 d . . . H9'A H 0.1556 -0.1400 0.4071 0.052 Uiso 1 1 calc R . . H9'B H 0.1509 -0.0859 0.3025 0.052 Uiso 1 1 calc R . . C9 C 0.15515(8) -0.1022(10) -0.1254(3) 0.0490(11) Uani 1 1 d . . . H9A H 0.1586 -0.1727 -0.0639 0.059 Uiso 1 1 calc R . . H9B H 0.1515 -0.2590 -0.1659 0.059 Uiso 1 1 calc R . . C10' C 0.13079(7) 0.1693(9) 0.3675(3) 0.0425(10) Uani 1 1 d U . . H10A H 0.1266 0.2819 0.3135 0.051 Uiso 1 1 calc R . . H10D H 0.1350 0.2941 0.4186 0.051 Uiso 1 1 calc R . . C10 C 0.13259(7) 0.0818(9) -0.1374(3) 0.0444(11) Uani 1 1 d . . . H10B H 0.1361 0.2349 -0.0953 0.053 Uiso 1 1 calc R . . H10C H 0.1297 0.1581 -0.1981 0.053 Uiso 1 1 calc R . . C11' C 0.10819(7) 0.0093(9) 0.3780(3) 0.0399(10) Uani 1 1 d U . . C11 C 0.10947(7) -0.0563(9) -0.1235(3) 0.0405(10) Uani 1 1 d U . . C12 C 0.11198(8) -0.2050(9) -0.0366(3) 0.0459(11) Uani 1 1 d . . . H12A H 0.0964 -0.2864 -0.0322 0.069 Uiso 1 1 calc R . . H12B H 0.1170 -0.0776 0.0125 0.069 Uiso 1 1 calc R . . H12C H 0.1242 -0.3476 -0.0336 0.069 Uiso 1 1 calc R . . C12' C 0.11145(8) -0.1483(10) 0.4643(3) 0.0508(12) Uani 1 1 d . . . H12D H 0.0968 -0.2548 0.4653 0.076 Uiso 1 1 calc R . . H12E H 0.1142 -0.0217 0.5143 0.076 Uiso 1 1 calc R . . H12F H 0.1254 -0.2700 0.4688 0.076 Uiso 1 1 calc R . . C13' C 0.08566(7) 0.1757(9) 0.3633(3) 0.0434(11) Uani 1 1 d . . . H13A H 0.0829 0.3222 0.4000 0.052 Uiso 1 1 calc R . . C13 C 0.08772(7) 0.1270(9) -0.1387(3) 0.0447(11) Uani 1 1 d U . . H13B H 0.0857 0.2784 -0.1027 0.054 Uiso 1 1 calc R . . C14' C 0.06990(7) 0.0920(8) 0.2916(3) 0.0387(10) Uani 1 1 d . . . H14A H 0.0543 0.1662 0.2696 0.046 Uiso 1 1 calc R . . C14 C 0.07160(7) 0.0485(9) -0.2095(3) 0.0409(10) Uani 1 1 d . . . H14B H 0.0563 0.1304 -0.2317 0.049 Uiso 1 1 calc R . . C15' C 0.08091(7) -0.1318(9) 0.2535(2) 0.0359(9) Uani 1 1 d . . . C15 C 0.08163(7) -0.1852(9) -0.2466(3) 0.0407(10) Uani 1 1 d . . . C16' C 0.07088(7) -0.2767(9) 0.1779(3) 0.0395(10) Uani 1 1 d . . . C16 C 0.07096(7) -0.3191(9) -0.3237(2) 0.0384(10) Uani 1 1 d . . . C17 C 0.04704(8) -0.2661(10) -0.3723(3) 0.0436(11) Uani 1 1 d . . . C17' C 0.04711(8) -0.2353(9) 0.1275(3) 0.0428(11) Uani 1 1 d . . . C18' C 0.04311(7) -0.4325(9) 0.0519(2) 0.0398(10) Uani 1 1 d . . . H18A H 0.0302 -0.5653 0.0594 0.048 Uiso 1 1 calc R . . C18 C 0.04257(7) -0.4583(9) -0.4516(2) 0.0410(10) Uani 1 1 d . . . H18B H 0.0296 -0.5913 -0.4457 0.049 Uiso 1 1 calc R . . C19' C 0.08291(7) -0.4900(9) 0.1344(2) 0.0399(10) Uani 1 1 d . . . C19 C 0.08189(8) -0.5282(9) -0.3719(3) 0.0421(11) Uani 1 1 d . . . C20' C 0.03588(8) -0.2896(9) -0.0364(3) 0.0426(10) Uani 1 1 d . . . H20A H 0.0219 -0.1702 -0.0339 0.051 Uiso 1 1 calc R . . H20B H 0.0495 -0.1727 -0.0452 0.051 Uiso 1 1 calc R . . C20 C 0.03553(8) -0.3029(9) -0.5377(3) 0.0442(11) Uani 1 1 d . . . H20C H 0.0221 -0.1780 -0.5324 0.053 Uiso 1 1 calc R . . H20D H 0.0495 -0.1908 -0.5456 0.053 Uiso 1 1 calc R . . C21' C 0.02924(7) -0.4714(9) -0.1148(3) 0.0417(10) Uani 1 1 d . . . C21 C 0.02770(7) -0.4732(9) -0.6198(3) 0.0405(10) Uani 1 1 d . . . 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' 0.0440(16) 0.0371(18) 0.0357(15) -0.0048(13) 0.0089(13) -0.0021(13) O1 0.0361(15) 0.0405(18) 0.0402(16) -0.0028(13) 0.0013(13) 0.0024(13) O1W 0.0420(16) 0.0508(19) 0.0491(17) 0.0001(15) 0.0157(13) 0.0008(15) O2' 0.0405(17) 0.056(2) 0.0499(17) 0.0002(16) 0.0067(14) 0.0127(15) O2 0.0454(18) 0.057(2) 0.0435(16) -0.0022(16) 0.0089(14) 0.0051(16) O3 0.0455(17) 0.0536(19) 0.0341(15) -0.0033(15) 0.0056(13) 0.0038(15) O3' 0.0422(16) 0.0462(18) 0.0426(16) -0.0027(14) 0.0082(13) 0.0082(14) O4' 0.0495(18) 0.063(2) 0.0378(16) 0.0007(15) 0.0103(14) 0.0114(16) O4 0.0454(18) 0.072(2) 0.0479(18) -0.0055(18) 0.0090(14) 0.0199(17) O5 0.077(2) 0.062(2) 0.0388(16) -0.0038(16) 0.0155(16) -0.0154(19) O5' 0.066(2) 0.066(2) 0.0408(16) -0.0077(17) 0.0119(15) -0.0183(18) O6 0.076(2) 0.055(2) 0.0382(16) 0.0029(15) 0.0249(15) 0.0038(18) O6' 0.086(2) 0.057(2) 0.059(2) -0.0056(18) 0.0395(18) -0.012(2) C1 0.045(3) 0.098(5) 0.052(3) 0.002(3) 0.005(2) 0.000(3) C1' 0.054(3) 0.108(5) 0.067(3) -0.023(4) 0.013(3) -0.010(3) C2' 0.045(3) 0.091(4) 0.055(3) -0.015(3) 0.008(2) -0.002(3) C2 0.044(3) 0.070(4) 0.060(3) -0.002(3) 0.017(2) -0.011(3) C3 0.047(3) 0.059(3) 0.047(3) 0.006(2) 0.006(2) 0.001(2) C3' 0.038(2) 0.067(3) 0.046(3) -0.002(3) 0.0027(19) 0.005(2) C4 0.044(3) 0.054(3) 0.051(3) 0.004(2) 0.012(2) -0.003(2) C4' 0.050(3) 0.059(3) 0.048(3) -0.003(2) 0.004(2) -0.001(2) C5 0.042(3) 0.056(3) 0.051(3) 0.006(2) 0.009(2) -0.003(2) C5' 0.042(2) 0.060(3) 0.051(3) -0.002(3) 0.006(2) -0.003(2) C6' 0.040(2) 0.056(3) 0.044(2) -0.008(2) 0.007(2) 0.000(2) C6 0.043(2) 0.056(3) 0.047(2) 0.004(2) 0.0076(19) -0.003(2) C7' 0.039(2) 0.050(3) 0.052(3) -0.004(2) 0.006(2) 0.000(2) C7 0.041(2) 0.052(3) 0.050(3) -0.001(2) 0.013(2) -0.004(2) C8 0.041(2) 0.050(3) 0.052(3) 0.002(2) 0.009(2) -0.005(2) C8' 0.039(2) 0.054(3) 0.048(3) -0.001(2) 0.007(2) -0.002(2) C9' 0.038(2) 0.047(3) 0.045(2) -0.001(2) 0.0083(18) 0.001(2) C9 0.051(3) 0.046(3) 0.050(3) 0.006(2) 0.010(2) -0.005(2) C10' 0.039(2) 0.040(3) 0.048(2) 0.001(2) 0.006(2) -0.0016(19) C10 0.039(2) 0.043(3) 0.052(3) 0.000(2) 0.009(2) -0.003(2) C11' 0.047(2) 0.036(2) 0.036(2) -0.0048(19) 0.0070(18) -0.003(2) C11 0.041(2) 0.039(3) 0.040(2) -0.008(2) 0.0052(19) -0.0092(19) C12 0.053(3) 0.047(3) 0.039(2) -0.004(2) 0.012(2) -0.004(2) C12' 0.056(3) 0.053(3) 0.042(2) -0.003(2) 0.007(2) -0.005(2) C13' 0.044(2) 0.035(2) 0.052(3) -0.006(2) 0.011(2) 0.0010(19) C13 0.041(2) 0.041(3) 0.055(3) 0.002(2) 0.019(2) 0.001(2) C14' 0.043(2) 0.034(2) 0.044(2) -0.0001(19) 0.021(2) 0.0027(19) C14 0.041(2) 0.037(2) 0.043(2) 0.000(2) 0.0049(19) -0.001(2) C15' 0.034(2) 0.039(2) 0.035(2) 0.0064(19) 0.0058(17) 0.0015(18) C15 0.042(2) 0.042(3) 0.041(2) 0.006(2) 0.017(2) -0.002(2) C16' 0.042(2) 0.046(3) 0.032(2) 0.0035(19) 0.0106(18) -0.001(2) C16 0.044(2) 0.042(3) 0.030(2) -0.0036(18) 0.0087(18) 0.0031(19) C17 0.045(3) 0.056(3) 0.029(2) 0.005(2) 0.0049(19) -0.003(2) C17' 0.043(3) 0.052(3) 0.035(2) 0.006(2) 0.0106(19) 0.008(2) C18' 0.038(2) 0.045(3) 0.036(2) 0.002(2) 0.0071(17) 0.008(2) C18 0.040(2) 0.049(3) 0.035(2) 0.002(2) 0.0118(18) 0.008(2) C19' 0.047(3) 0.039(3) 0.033(2) -0.0009(19) 0.0062(19) -0.006(2) C19 0.045(3) 0.049(3) 0.035(2) 0.004(2) 0.0145(19) 0.001(2) C20' 0.042(2) 0.045(3) 0.038(2) 0.003(2) 0.0024(19) 0.003(2) C20 0.051(3) 0.044(3) 0.039(2) 0.004(2) 0.013(2) 0.003(2) C21' 0.039(2) 0.044(3) 0.042(2) 0.005(2) 0.0086(19) 0.008(2) C21 0.046(2) 0.034(2) 0.040(2) 0.0060(19) 0.0059(19) 0.006(2) _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' C15' 1.337(4) . ? O1' C11' 1.500(5) . ? O1 C15 1.319(5) . ? O1 C11 1.499(5) . ? O1W H1 0.8400 . ? O1W H2 0.8401 . ? O2' C19' 1.197(5) . ? O2 C19 1.220(5) . ? O3 C19 1.376(5) . ? O3 C18 1.469(4) . ? O3' C19' 1.390(5) . ? O3' C18' 1.457(4) . ? O4' C17' 1.250(5) . ? O4 C17 1.234(5) . ? O5 C21 1.339(5) . ? O5 H5C 0.8400 . ? O5' C21' 1.328(5) . ? O5' H5'C 0.8400 . ? O6 C21 1.200(5) . ? O6' C21' 1.202(5) . ? C1 C2 1.527(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1' C2' 1.528(7) . ? C1' H1'A 0.9800 . ? C1' H1'B 0.9800 . ? C1' H1'C 0.9800 . ? C2' C3' 1.515(6) . ? C2' H2'A 0.9900 . ? C2' H2'B 0.9900 . ? C2 C3 1.522(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3' C4' 1.522(6) . ? C3' H3'A 0.9900 . ? C3' H3'B 0.9900 . ? C4 C5 1.520(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4' C5' 1.527(6) . ? C4' H4'A 0.9900 . ? C4' H4'B 0.9900 . ? C5 C6 1.526(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5' C6' 1.525(6) . ? C5' H5'A 0.9900 . ? C5' H5'B 0.9900 . ? C6' C7' 1.528(6) . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C6 C7 1.525(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7' C8' 1.531(6) . ? C7' H7'A 0.9900 . ? C7' H7'B 0.9900 . ? C7 C8 1.516(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.534(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8' C9' 1.521(6) . ? C8' H8'A 0.9900 . ? C8' H8'B 0.9900 . ? C9' C10' 1.528(5) . ? C9' H9'A 0.9900 . ? C9' H9'B 0.9900 . ? C9 C10 1.541(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10' C11' 1.531(5) . ? C10' H10A 0.9900 . ? C10' H10D 0.9900 . ? C10 C11 1.520(5) . ? C10 H10B 0.9900 . ? C10 H10C 0.9900 . ? C11' C13' 1.489(6) . ? C11' C12' 1.518(6) . ? C11 C13 1.502(6) . ? C11 C12 1.508(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12' H12D 0.9800 . ? C12' H12E 0.9800 . ? C12' H12F 0.9800 . ? C13' C14' 1.336(6) . ? C13' H13A 0.9500 . ? C13 C14 1.329(6) . ? C13 H13B 0.9500 . ? C14' C15' 1.446(6) . ? C14' H14A 0.9500 . ? C14 C15 1.450(6) . ? C14 H14B 0.9500 . ? C15' C16' 1.387(5) . ? C15 C16 1.386(6) . ? C16' C17' 1.421(5) . ? C16' C19' 1.481(6) . ? C16 C17 1.428(6) . ? C16 C19 1.475(6) . ? C17 C18 1.527(6) . ? C17' C18' 1.500(6) . ? C18' C20' 1.513(5) . ? C18' H18A 1.0000 . ? C18 C20 1.514(5) . ? C18 H18B 1.0000 . ? C20' C21' 1.491(6) . ? C20' H20A 0.9900 . ? C20' H20B 0.9900 . ? C20 C21 1.510(6) . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? 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 C15' O1' C11' 109.1(3) . . ? C15 O1 C11 108.9(3) . . ? H1 O1W H2 114.9 . . ? C19 O3 C18 110.0(3) . . ? C19' O3' C18' 112.0(3) . . ? C21 O5 H5C 109.5 . . ? C21' O5' H5'C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2' C1' H1'A 109.5 . . ? C2' C1' H1'B 109.5 . . ? H1'A C1' H1'B 109.5 . . ? C2' C1' H1'C 109.5 . . ? H1'A C1' H1'C 109.5 . . ? H1'B C1' H1'C 109.5 . . ? C3' C2' C1' 114.3(5) . . ? C3' C2' H2'A 108.7 . . ? C1' C2' H2'A 108.7 . . ? C3' C2' H2'B 108.7 . . ? C1' C2' H2'B 108.7 . . ? H2'A C2' H2'B 107.6 . . ? C3 C2 C1 113.0(4) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 114.2(4) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C2' C3' C4' 114.6(4) . . ? C2' C3' H3'A 108.6 . . ? C4' C3' H3'A 108.6 . . ? C2' C3' H3'B 108.6 . . ? C4' C3' H3'B 108.6 . . ? H3'A C3' H3'B 107.6 . . ? C5 C4 C3 114.9(4) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.5 . . ? C3' C4' C5' 113.8(4) . . ? C3' C4' H4'A 108.8 . . ? C5' C4' H4'A 108.8 . . ? C3' C4' H4'B 108.8 . . ? C5' C4' H4'B 108.8 . . ? H4'A C4' H4'B 107.7 . . ? C4 C5 C6 114.1(4) . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C6' C5' C4' 114.3(4) . . ? C6' C5' H5'A 108.7 . . ? C4' C5' H5'A 108.7 . . ? C6' C5' H5'B 108.7 . . ? C4' C5' H5'B 108.7 . . ? H5'A C5' H5'B 107.6 . . ? C5' C6' C7' 113.9(4) . . ? C5' C6' H6'A 108.8 . . ? C7' C6' H6'A 108.8 . . ? C5' C6' H6'B 108.8 . . ? C7' C6' H6'B 108.8 . . ? H6'A C6' H6'B 107.7 . . ? C7 C6 C5 114.2(4) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6' C7' C8' 113.8(4) . . ? C6' C7' H7'A 108.8 . . ? C8' C7' H7'A 108.8 . . ? C6' C7' H7'B 108.8 . . ? C8' C7' H7'B 108.8 . . ? H7'A C7' H7'B 107.7 . . ? C8 C7 C6 113.3(4) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 113.2(4) . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C9' C8' C7' 113.6(4) . . ? C9' C8' H8'A 108.8 . . ? C7' C8' H8'A 108.8 . . ? C9' C8' H8'B 108.8 . . ? C7' C8' H8'B 108.8 . . ? H8'A C8' H8'B 107.7 . . ? C8' C9' C10' 112.1(4) . . ? C8' C9' H9'A 109.2 . . ? C10' C9' H9'A 109.2 . . ? C8' C9' H9'B 109.2 . . ? C10' C9' H9'B 109.2 . . ? H9'A C9' H9'B 107.9 . . ? C8 C9 C10 113.4(4) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9' C10' C11' 116.5(4) . . ? C9' C10' H10A 108.2 . . ? C11' C10' H10A 108.2 . . ? C9' C10' H10D 108.2 . . ? C11' C10' H10D 108.2 . . ? H10A C10' H10D 107.3 . . ? C11 C10 C9 115.2(4) . . ? C11 C10 H10B 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10C 108.5 . . ? C9 C10 H10C 108.5 . . ? H10B C10 H10C 107.5 . . ? C13' C11' O1' 101.7(3) . . ? C13' C11' C12' 111.6(4) . . ? O1' C11' C12' 108.4(3) . . ? C13' C11' C10' 113.4(4) . . ? O1' C11' C10' 107.4(3) . . ? C12' C11' C10' 113.4(3) . . ? O1 C11 C13 101.6(3) . . ? O1 C11 C12 109.2(3) . . ? C13 C11 C12 111.3(4) . . ? O1 C11 C10 105.9(3) . . ? C13 C11 C10 113.6(4) . . ? C12 C11 C10 114.3(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11' C12' H12D 109.5 . . ? C11' C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11' C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C14' C13' C11' 111.1(4) . . ? C14' C13' H13A 124.5 . . ? C11' C13' H13A 124.5 . . ? C14 C13 C11 110.7(4) . . ? C14 C13 H13B 124.6 . . ? C11 C13 H13B 124.6 . . ? C13' C14' C15' 107.7(4) . . ? C13' C14' H14A 126.1 . . ? C15' C14' H14A 126.1 . . ? C13 C14 C15 107.4(4) . . ? C13 C14 H14B 126.3 . . ? C15 C14 H14B 126.3 . . ? O1' C15' C16' 122.8(4) . . ? O1' C15' C14' 110.4(3) . . ? C16' C15' C14' 126.8(4) . . ? O1 C15 C16 123.3(4) . . ? O1 C15 C14 111.2(4) . . ? C16 C15 C14 125.5(4) . . ? C15' C16' C17' 124.5(4) . . ? C15' C16' C19' 126.9(4) . . ? C17' C16' C19' 108.6(4) . . ? C15 C16 C17 124.3(4) . . ? C15 C16 C19 127.7(4) . . ? C17 C16 C19 107.9(4) . . ? O4 C17 C16 132.1(4) . . ? O4 C17 C18 120.8(4) . . ? C16 C17 C18 107.1(4) . . ? O4' C17' C16' 130.2(4) . . ? O4' C17' C18' 121.7(4) . . ? C16' C17' C18' 108.1(4) . . ? O3' C18' C17' 104.4(3) . . ? O3' C18' C20' 111.8(3) . . ? C17' C18' C20' 111.5(4) . . ? O3' C18' H18A 109.7 . . ? C17' C18' H18A 109.7 . . ? C20' C18' H18A 109.7 . . ? O3 C18 C20 110.6(3) . . ? O3 C18 C17 105.0(3) . . ? C20 C18 C17 111.0(4) . . ? O3 C18 H18B 110.1 . . ? C20 C18 H18B 110.1 . . ? C17 C18 H18B 110.1 . . ? O2' C19' O3' 120.8(4) . . ? O2' C19' C16' 132.5(4) . . ? O3' C19' C16' 106.8(3) . . ? O2 C19 O3 120.6(4) . . ? O2 C19 C16 129.7(4) . . ? O3 C19 C16 109.7(3) . . ? C21' C20' C18' 115.2(4) . . ? C21' C20' H20A 108.5 . . ? C18' C20' H20A 108.5 . . ? C21' C20' H20B 108.5 . . ? C18' C20' H20B 108.5 . . ? H20A C20' H20B 107.5 . . ? C21 C20 C18 115.7(4) . . ? C21 C20 H20C 108.4 . . ? C18 C20 H20C 108.4 . . ? C21 C20 H20D 108.4 . . ? C18 C20 H20D 108.4 . . ? H20C C20 H20D 107.4 . . ? O6' C21' O5' 122.2(4) . . ? O6' C21' C20' 125.1(4) . . ? O5' C21' C20' 112.7(4) . . ? O6 C21 O5 123.1(4) . . ? O6 C21 C20 124.6(4) . . ? O5 C21 C20 112.2(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -178.4(4) . . . . ? C1' C2' C3' C4' -178.7(4) . . . . ? C2 C3 C4 C5 179.9(4) . . . . ? C2' C3' C4' C5' 178.4(4) . . . . ? C3 C4 C5 C6 -178.2(4) . . . . ? C3' C4' C5' C6' -178.1(4) . . . . ? C4' C5' C6' C7' -179.5(4) . . . . ? C4 C5 C6 C7 179.5(4) . . . . ? C5' C6' C7' C8' -179.0(4) . . . . ? C5 C6 C7 C8 179.5(4) . . . . ? C6 C7 C8 C9 -178.0(4) . . . . ? C6' C7' C8' C9' -176.6(4) . . . . ? C7' C8' C9' C10' -176.2(4) . . . . ? C7 C8 C9 C10 174.7(4) . . . . ? C8' C9' C10' C11' -166.0(4) . . . . ? C8 C9 C10 C11 177.8(3) . . . . ? C15' O1' C11' C13' 1.3(4) . . . . ? C15' O1' C11' C12' 119.0(3) . . . . ? C15' O1' C11' C10' -118.1(3) . . . . ? C9' C10' C11' C13' -166.9(4) . . . . ? C9' C10' C11' O1' -55.3(4) . . . . ? C9' C10' C11' C12' 64.5(5) . . . . ? C15 O1 C11 C13 1.6(4) . . . . ? C15 O1 C11 C12 119.2(4) . . . . ? C15 O1 C11 C10 -117.3(4) . . . . ? C9 C10 C11 O1 -67.4(4) . . . . ? C9 C10 C11 C13 -178.1(4) . . . . ? C9 C10 C11 C12 52.8(5) . . . . ? O1' C11' C13' C14' -0.3(5) . . . . ? C12' C11' C13' C14' -115.8(4) . . . . ? C10' C11' C13' C14' 114.7(4) . . . . ? O1 C11 C13 C14 -0.2(4) . . . . ? C12 C11 C13 C14 -116.2(4) . . . . ? C10 C11 C13 C14 113.1(4) . . . . ? C11' C13' C14' C15' -0.7(5) . . . . ? C11 C13 C14 C15 -1.2(5) . . . . ? C11' O1' C15' C16' 179.1(4) . . . . ? C11' O1' C15' C14' -1.8(4) . . . . ? C13' C14' C15' O1' 1.6(5) . . . . ? C13' C14' C15' C16' -179.3(4) . . . . ? C11 O1 C15 C16 176.4(4) . . . . ? C11 O1 C15 C14 -2.5(4) . . . . ? C13 C14 C15 O1 2.4(5) . . . . ? C13 C14 C15 C16 -176.5(4) . . . . ? O1' C15' C16' C17' 175.6(4) . . . . ? C14' C15' C16' C17' -3.4(7) . . . . ? O1' C15' C16' C19' -6.7(7) . . . . ? C14' C15' C16' C19' 174.3(4) . . . . ? O1 C15 C16 C17 173.4(4) . . . . ? C14 C15 C16 C17 -7.9(7) . . . . ? O1 C15 C16 C19 -9.2(7) . . . . ? C14 C15 C16 C19 169.5(4) . . . . ? C15 C16 C17 O4 -0.5(8) . . . . ? C19 C16 C17 O4 -178.3(5) . . . . ? C15 C16 C17 C18 -179.7(4) . . . . ? C19 C16 C17 C18 2.5(5) . . . . ? C15' C16' C17' O4' -0.3(8) . . . . ? C19' C16' C17' O4' -178.4(4) . . . . ? C15' C16' C17' C18' -179.6(4) . . . . ? C19' C16' C17' C18' 2.4(5) . . . . ? C19' O3' C18' C17' 3.6(4) . . . . ? C19' O3' C18' C20' 124.3(4) . . . . ? O4' C17' C18' O3' 177.1(4) . . . . ? C16' C17' C18' O3' -3.6(4) . . . . ? O4' C17' C18' C20' 56.2(5) . . . . ? C16' C17' C18' C20' -124.4(4) . . . . ? C19 O3 C18 C20 125.2(4) . . . . ? C19 O3 C18 C17 5.4(4) . . . . ? O4 C17 C18 O3 175.9(4) . . . . ? C16 C17 C18 O3 -4.7(4) . . . . ? O4 C17 C18 C20 56.4(6) . . . . ? C16 C17 C18 C20 -124.2(4) . . . . ? C18' O3' C19' O2' 178.7(4) . . . . ? C18' O3' C19' C16' -2.2(4) . . . . ? C15' C16' C19' O2' 0.8(8) . . . . ? C17' C16' C19' O2' 178.8(5) . . . . ? C15' C16' C19' O3' -178.2(4) . . . . ? C17' C16' C19' O3' -0.2(4) . . . . ? C18 O3 C19 O2 178.4(4) . . . . ? C18 O3 C19 C16 -4.1(4) . . . . ? C15 C16 C19 O2 0.5(8) . . . . ? C17 C16 C19 O2 178.2(4) . . . . ? C15 C16 C19 O3 -176.8(4) . . . . ? C17 C16 C19 O3 0.9(5) . . . . ? O3' C18' C20' C21' 69.1(5) . . . . ? C17' C18' C20' C21' -174.4(3) . . . . ? O3 C18 C20 C21 71.0(5) . . . . ? C17 C18 C20 C21 -172.8(3) . . . . ? C18' C20' C21' O6' -131.5(5) . . . . ? C18' C20' C21' O5' 49.8(5) . . . . ? C18 C20 C21 O6 -142.0(4) . . . . ? C18 C20 C21 O5 41.2(5) . . . . ? 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 O1W H1 O4 0.84 2.03 2.717(4) 138.1 2_544 O1W H1 O6' 0.84 2.49 3.129(5) 133.1 2_544 O1W H2 O4' 0.84 2.06 2.748(4) 138.5 1_544 O1W H2 O6 0.84 2.34 2.961(4) 131.0 1_545 O5 H5C O1W 0.84 1.82 2.663(4) 176.0 . O5' H5'C O1W 0.84 1.84 2.675(4) 177.2 2_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.174 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.042