Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'K. Undheim' _publ_contact_author_address ; Department of Chemistry University of Oslo Pb 1033 Blindern Oslo N-0315 NORWAY ; _publ_contact_author_email KJELL.UNDHEIM@KJEMI.UIO.NO _publ_section_title ; Stereoselective preparation of (RP)-8-hetaryladenosine-3',5'-cyclic phosphorothioic acids ; loop_ _publ_author_name 'K Undheim' 'Mioara Andrei' 'Vidar Bjornstad' 'Jo Klaveness' 'Geir Langli' 'Christian Romming' ; K.Tasken ; data_7a _database_code_depnum_ccdc_archive 'CCDC 625282' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Sp)-8-(2-Furyl)adenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N- phenylphosphoramidate ; _chemical_name_common ; (Sp)-8-(2-Furyl)adenosine-2'-O-(tert-butyldimethylsilyl)- 3',5'-cyclic N-phenylphosphoramidate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H33 N6 O6 P Si' _chemical_formula_weight 584.64 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9131(2) _cell_length_b 13.5228(2) _cell_length_c 20.2901(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2994.33(8) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39032 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.30 _reflns_number_total 7452 _reflns_number_gt 7290 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0383P)^2^+0.5546P] 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 refall _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 0.02(5) _refine_ls_number_reflns 7452 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.052 _refine_ls_shift/su_mean 0.002 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 Si1 Si 0.18064(3) 0.91931(2) 0.199145(14) 0.01701(6) Uani 1 1 d . . . P1 P 0.35539(3) 0.58371(2) 0.230808(13) 0.01873(6) Uani 1 1 d . . . O1 O 0.42113(9) 1.02487(6) -0.00779(4) 0.02413(18) Uani 1 1 d . . . O2 O 0.48835(7) 0.74764(6) 0.06460(4) 0.01802(15) Uani 1 1 d . . . O3 O 0.29468(7) 0.87622(6) 0.15225(4) 0.01825(15) Uani 1 1 d . . . O4 O 0.29704(7) 0.68319(6) 0.20219(4) 0.01851(15) Uani 1 1 d . . . O5 O 0.49690(8) 0.59111(6) 0.21161(4) 0.02308(17) Uani 1 1 d . . . O6 O 0.29690(9) 0.49226(6) 0.20674(4) 0.02535(18) Uani 1 1 d . . . N1 N 0.20782(9) 0.58728(7) -0.12058(5) 0.02008(18) Uani 1 1 d . . . N2 N 0.34785(10) 0.59615(7) 0.30996(5) 0.02177(19) Uani 1 1 d . . . H02 H 0.3233(19) 0.5428(16) 0.3300(10) 0.043(5) Uiso 1 1 d . . . N3 N 0.25674(10) 0.64715(7) -0.01132(5) 0.02011(19) Uani 1 1 d . . . N6 N 0.24043(10) 0.68077(8) -0.21602(5) 0.02058(19) Uani 1 1 d . . . H6B H 0.2218(18) 0.6272(15) -0.2406(10) 0.039(5) Uiso 1 1 d . . . H6A H 0.2807(16) 0.7283(13) -0.2358(8) 0.026(4) Uiso 1 1 d . . . N7 N 0.35384(9) 0.83478(7) -0.12489(4) 0.01747(17) Uani 1 1 d . . . N9 N 0.35406(9) 0.81015(6) -0.01444(4) 0.01641(17) Uani 1 1 d . . . C1 C 0.44948(11) 0.96548(8) -0.06053(6) 0.0200(2) Uani 1 1 d . . . C2 C 0.21317(11) 0.58161(9) -0.05431(5) 0.0214(2) Uani 1 1 d . . . H2 H 0.1829(16) 0.5209(12) -0.0356(8) 0.023(4) Uiso 1 1 d . . . C3 C 0.53405(14) 1.00969(10) -0.09970(7) 0.0299(3) Uani 1 1 d . . . H3 H 0.5695(18) 0.9831(14) -0.1376(10) 0.036(5) Uiso 1 1 d . . . C4 C 0.30038(10) 0.72758(8) -0.04224(5) 0.01643(19) Uani 1 1 d . . . C5 C 0.30104(10) 0.74434(8) -0.10983(5) 0.01647(19) Uani 1 1 d . . . C6 C 0.25010(10) 0.67033(8) -0.15011(5) 0.0173(2) Uani 1 1 d . . . C7 C 0.56007(15) 1.10308(10) -0.06935(8) 0.0359(3) Uani 1 1 d . . . H7 H 0.608(2) 1.1526(18) -0.0832(11) 0.059(7) Uiso 1 1 d . . . C8 C 0.38590(10) 0.87127(8) -0.06726(5) 0.01655(19) Uani 1 1 d . . . C9 C 0.49078(14) 1.10866(9) -0.01483(7) 0.0313(3) Uani 1 1 d . . . H9 H 0.4842(18) 1.1584(15) 0.0173(10) 0.042(5) Uiso 1 1 d . . . C10 C 0.39228(9) 0.81882(8) 0.05376(5) 0.01553(19) Uani 1 1 d . . . H10 H 0.4230(13) 0.8859(11) 0.0599(7) 0.014(3) Uiso 1 1 d . . . C11 C 0.28914(10) 0.79925(8) 0.10583(5) 0.01507(18) Uani 1 1 d . . . H11 H 0.2097(15) 0.7957(11) 0.0844(7) 0.019(3) Uiso 1 1 d . . . C12 C 0.33383(9) 0.70165(7) 0.13508(5) 0.01500(19) Uani 1 1 d . . . H12 H 0.3100(14) 0.6473(11) 0.1082(7) 0.014(3) Uiso 1 1 d . . . C13 C 0.47232(10) 0.71353(8) 0.13046(5) 0.01616(19) Uani 1 1 d . . . H13 H 0.4999(13) 0.7636(10) 0.1617(7) 0.010(3) Uiso 1 1 d . . . C14 C 0.53383(11) 0.61572(9) 0.14454(6) 0.0214(2) Uani 1 1 d . . . H14B H 0.5015(15) 0.5664(12) 0.1163(8) 0.023(4) Uiso 1 1 d . . . H14A H 0.6193(16) 0.6194(12) 0.1463(8) 0.026(4) Uiso 1 1 d . . . C15 C 0.05965(14) 0.82479(12) 0.21050(10) 0.0398(4) Uani 1 1 d . . . H15C H -0.005(2) 0.8537(17) 0.2306(11) 0.054(6) Uiso 1 1 d . . . H15B H 0.094(4) 0.763(3) 0.2278(19) 0.125(13) Uiso 1 1 d . . . H15A H 0.033(3) 0.807(2) 0.1724(16) 0.090(10) Uiso 1 1 d . . . C16 C 0.25103(14) 0.94782(13) 0.27989(7) 0.0352(3) Uani 1 1 d . . . H16C H 0.203(2) 0.9933(16) 0.3053(10) 0.048(5) Uiso 1 1 d . . . H16B H 0.326(3) 0.981(2) 0.2708(12) 0.071(7) Uiso 1 1 d . . . H16A H 0.272(3) 0.885(2) 0.3053(14) 0.085(9) Uiso 1 1 d . . . C17 C 0.11871(17) 1.03304(12) 0.15754(8) 0.0423(4) Uani 1 1 d . . . C18 C 0.0646(4) 1.0051(3) 0.08985(10) 0.0827(12) Uani 1 1 d . . . H18C H 0.131(3) 0.986(2) 0.0577(13) 0.072(8) Uiso 1 1 d . . . H18B H 0.033(3) 1.061(2) 0.0721(15) 0.088(9) Uiso 1 1 d . . . H18A H 0.019(4) 0.962(4) 0.087(2) 0.14(2) Uiso 1 1 d . . . C19 C 0.2234(3) 1.10856(14) 0.14967(17) 0.0818(10) Uani 1 1 d . . . H19C H 0.286(2) 1.0804(17) 0.1207(11) 0.054(6) Uiso 1 1 d . . . H19B H 0.184(4) 1.161(3) 0.128(2) 0.131(13) Uiso 1 1 d . . . H19A H 0.256(4) 1.138(3) 0.198(2) 0.134(15) Uiso 1 1 d . . . C20 C 0.0163(2) 1.07935(17) 0.19986(10) 0.0543(5) Uani 1 1 d . . . H20C H -0.017(2) 1.131(2) 0.1798(13) 0.071(7) Uiso 1 1 d . . . H20B H 0.041(2) 1.1022(16) 0.2457(12) 0.056(6) Uiso 1 1 d . . . H20A H -0.053(3) 1.033(2) 0.2044(15) 0.092(10) Uiso 1 1 d . . . C21 C 0.37458(11) 0.68186(9) 0.34811(6) 0.0214(2) Uani 1 1 d . . . C22 C 0.29691(13) 0.70530(10) 0.40063(6) 0.0283(3) Uani 1 1 d . . . H22 H 0.2241(18) 0.6661(15) 0.4054(9) 0.038(5) Uiso 1 1 d . . . C23 C 0.32219(16) 0.78770(11) 0.43971(7) 0.0352(3) Uani 1 1 d . . . H23 H 0.2655(18) 0.8040(14) 0.4758(10) 0.041(5) Uiso 1 1 d . . . C24 C 0.42300(17) 0.84680(11) 0.42652(7) 0.0373(3) Uani 1 1 d . . . H24 H 0.4327(18) 0.9065(15) 0.4524(9) 0.041(5) Uiso 1 1 d . . . C25 C 0.49884(15) 0.82448(10) 0.37402(7) 0.0341(3) Uani 1 1 d . . . H25 H 0.573(2) 0.8669(15) 0.3627(10) 0.047(5) Uiso 1 1 d . . . C26 C 0.47584(13) 0.74144(10) 0.33503(6) 0.0267(2) Uani 1 1 d . . . H26 H 0.5300(18) 0.7238(14) 0.3008(10) 0.039(5) Uiso 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 Si1 0.01637(13) 0.01765(13) 0.01703(12) -0.00274(10) 0.00009(10) 0.00041(11) P1 0.02316(13) 0.01768(12) 0.01534(12) 0.00374(10) 0.00125(10) -0.00041(11) O1 0.0317(4) 0.0146(3) 0.0262(4) -0.0020(3) -0.0036(4) -0.0025(3) O2 0.0180(3) 0.0203(4) 0.0157(3) 0.0040(3) 0.0025(3) 0.0017(3) O3 0.0189(4) 0.0171(3) 0.0188(3) -0.0051(3) 0.0017(3) -0.0002(3) O4 0.0206(4) 0.0204(4) 0.0146(3) 0.0042(3) 0.0029(3) 0.0018(3) O5 0.0234(4) 0.0249(4) 0.0209(4) 0.0083(3) 0.0033(3) 0.0053(3) O6 0.0366(5) 0.0205(4) 0.0189(4) 0.0027(3) 0.0002(3) -0.0042(3) N1 0.0234(4) 0.0185(4) 0.0184(4) -0.0030(4) 0.0001(3) -0.0028(4) N2 0.0303(5) 0.0190(4) 0.0160(4) 0.0033(3) 0.0008(4) -0.0046(4) N3 0.0254(5) 0.0180(4) 0.0169(4) 0.0001(3) 0.0010(4) -0.0048(4) N6 0.0253(5) 0.0210(4) 0.0155(4) -0.0021(3) -0.0013(3) -0.0029(4) N7 0.0198(4) 0.0166(4) 0.0160(4) 0.0012(3) -0.0007(3) -0.0008(3) N9 0.0218(4) 0.0135(4) 0.0139(4) 0.0002(3) -0.0007(3) -0.0021(3) C1 0.0250(5) 0.0169(5) 0.0180(5) 0.0022(4) -0.0054(4) -0.0022(4) C2 0.0259(5) 0.0187(5) 0.0196(5) -0.0002(4) 0.0017(4) -0.0054(4) C3 0.0347(7) 0.0293(6) 0.0258(6) 0.0073(5) -0.0023(5) -0.0113(5) C4 0.0180(5) 0.0160(4) 0.0153(4) -0.0012(4) -0.0006(4) -0.0010(4) C5 0.0174(5) 0.0163(5) 0.0157(4) -0.0007(4) 0.0001(4) 0.0009(4) C6 0.0164(5) 0.0183(5) 0.0172(5) -0.0027(4) 0.0000(4) 0.0012(4) C7 0.0411(7) 0.0254(6) 0.0412(7) 0.0113(6) -0.0104(6) -0.0167(5) C8 0.0189(5) 0.0155(5) 0.0152(4) 0.0026(4) 0.0000(4) -0.0001(4) C9 0.0398(7) 0.0170(5) 0.0371(7) 0.0018(5) -0.0135(6) -0.0057(5) C10 0.0182(5) 0.0150(4) 0.0134(4) -0.0001(3) -0.0008(4) -0.0015(4) C11 0.0163(5) 0.0153(4) 0.0136(4) -0.0006(4) 0.0000(4) -0.0002(3) C12 0.0176(5) 0.0150(4) 0.0124(4) 0.0011(3) 0.0016(4) -0.0009(4) C13 0.0169(5) 0.0168(5) 0.0148(4) 0.0025(4) 0.0009(4) 0.0004(4) C14 0.0223(5) 0.0214(5) 0.0205(5) 0.0054(4) 0.0044(4) 0.0046(4) C15 0.0222(6) 0.0341(7) 0.0632(11) -0.0125(7) 0.0098(7) -0.0079(5) C16 0.0274(6) 0.0523(9) 0.0259(6) -0.0168(6) -0.0027(5) 0.0045(6) C17 0.0537(9) 0.0387(8) 0.0345(7) 0.0103(6) 0.0136(7) 0.0270(7) C18 0.104(2) 0.119(2) 0.0258(8) 0.0114(11) -0.0040(10) 0.080(2) C19 0.105(2) 0.0249(8) 0.115(2) 0.0267(11) 0.0625(18) 0.0201(10) C20 0.0623(12) 0.0558(10) 0.0448(9) 0.0072(9) 0.0127(8) 0.0410(10) C21 0.0267(5) 0.0196(5) 0.0181(5) 0.0037(4) -0.0031(4) 0.0019(4) C22 0.0308(6) 0.0307(6) 0.0233(5) 0.0022(5) 0.0011(5) 0.0028(5) C23 0.0483(8) 0.0334(7) 0.0239(6) -0.0018(5) 0.0002(6) 0.0124(6) C24 0.0622(10) 0.0233(6) 0.0263(6) -0.0027(5) -0.0097(6) 0.0026(6) C25 0.0460(8) 0.0265(6) 0.0300(6) 0.0022(5) -0.0073(6) -0.0086(6) C26 0.0315(6) 0.0259(6) 0.0229(6) 0.0016(5) -0.0009(5) -0.0033(5) _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 Si1 O3 1.6715(8) . ? Si1 C16 1.8501(14) . ? Si1 C15 1.8521(15) . ? Si1 C17 1.8801(15) . ? P1 O6 1.4748(9) . ? P1 O5 1.5959(9) . ? P1 O4 1.5977(8) . ? P1 N2 1.6168(10) . ? O1 C9 1.3719(15) . ? O1 C1 1.3733(14) . ? O2 C13 1.4244(12) . ? O2 C10 1.4402(13) . ? O3 C11 1.4050(12) . ? O4 C12 1.4413(12) . ? O5 C14 1.4578(13) . ? N1 C2 1.3481(14) . ? N1 C6 1.3539(14) . ? N2 C21 1.4240(15) . ? N2 H02 0.87(2) . ? N3 C2 1.3313(15) . ? N3 C4 1.3429(14) . ? N6 C6 1.3488(14) . ? N6 H6B 0.90(2) . ? N6 H6A 0.876(18) . ? N7 C8 1.3165(14) . ? N7 C5 1.3861(13) . ? N9 C4 1.3813(13) . ? N9 C8 1.3974(13) . ? N9 C10 1.4501(13) . ? C1 C3 1.3568(18) . ? C1 C8 1.4570(15) . ? C2 H2 0.963(16) . ? C3 C7 1.4335(19) . ? C3 H3 0.93(2) . ? C4 C5 1.3900(14) . ? C5 C6 1.4067(14) . ? C7 C9 1.342(2) . ? C7 H7 0.90(2) . ? C9 H9 0.94(2) . ? C10 C11 1.5662(14) . ? C10 H10 0.975(14) . ? C11 C12 1.5272(14) . ? C11 H11 0.970(16) . ? C12 C13 1.5228(14) . ? C12 H12 0.951(15) . ? C13 C14 1.5105(15) . ? C13 H13 0.975(14) . ? C14 H14B 0.947(17) . ? C14 H14A 0.935(17) . ? C15 H15C 0.90(2) . ? C15 H15B 0.98(4) . ? C15 H15A 0.86(3) . ? C16 H16C 0.96(2) . ? C16 H16B 0.95(3) . ? C16 H16A 1.02(3) . ? C17 C19 1.541(3) . ? C17 C18 1.542(3) . ? C17 C20 1.542(2) . ? C18 H18C 1.01(3) . ? C18 H18B 0.91(3) . ? C18 H18A 0.77(5) . ? C19 H19C 0.98(2) . ? C19 H19B 0.94(4) . ? C19 H19A 1.12(4) . ? C20 H20C 0.88(3) . ? C20 H20B 1.02(2) . ? C20 H20A 0.99(3) . ? C21 C26 1.3931(18) . ? C21 C22 1.3981(18) . ? C22 C23 1.395(2) . ? C22 H22 0.96(2) . ? C23 C24 1.386(2) . ? C23 H23 0.98(2) . ? C24 C25 1.382(2) . ? C24 H24 0.97(2) . ? C25 C26 1.3963(19) . ? C25 H25 1.02(2) . ? C26 H26 0.94(2) . ? 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 O3 Si1 C16 105.52(5) . . ? O3 Si1 C15 111.17(6) . . ? C16 Si1 C15 109.25(9) . . ? O3 Si1 C17 107.29(6) . . ? C16 Si1 C17 112.11(8) . . ? C15 Si1 C17 111.35(9) . . ? O6 P1 O5 112.99(5) . . ? O6 P1 O4 114.40(5) . . ? O5 P1 O4 104.13(4) . . ? O6 P1 N2 113.22(5) . . ? O5 P1 N2 106.56(5) . . ? O4 P1 N2 104.66(5) . . ? C9 O1 C1 106.08(10) . . ? C13 O2 C10 105.68(8) . . ? C11 O3 Si1 127.43(7) . . ? C12 O4 P1 112.22(7) . . ? C14 O5 P1 120.65(7) . . ? C2 N1 C6 118.28(10) . . ? C21 N2 P1 127.90(8) . . ? C21 N2 H02 118.9(13) . . ? P1 N2 H02 113.2(13) . . ? C2 N3 C4 111.09(9) . . ? C6 N6 H6B 118.8(12) . . ? C6 N6 H6A 119.5(11) . . ? H6B N6 H6A 116.6(16) . . ? C8 N7 C5 104.20(9) . . ? C4 N9 C8 105.69(9) . . ? C4 N9 C10 125.25(9) . . ? C8 N9 C10 127.77(9) . . ? C3 C1 O1 110.61(10) . . ? C3 C1 C8 130.87(12) . . ? O1 C1 C8 118.49(10) . . ? N3 C2 N1 129.12(11) . . ? N3 C2 H2 115.6(9) . . ? N1 C2 H2 115.3(9) . . ? C1 C3 C7 105.74(13) . . ? C1 C3 H3 126.6(12) . . ? C7 C3 H3 127.7(12) . . ? N3 C4 N9 127.90(9) . . ? N3 C4 C5 126.50(10) . . ? N9 C4 C5 105.60(9) . . ? N7 C5 C4 111.32(9) . . ? N7 C5 C6 131.60(10) . . ? C4 C5 C6 117.08(10) . . ? N6 C6 N1 119.92(10) . . ? N6 C6 C5 122.18(10) . . ? N1 C6 C5 117.89(10) . . ? C9 C7 C3 106.98(12) . . ? C9 C7 H7 123.1(15) . . ? C3 C7 H7 129.7(15) . . ? N7 C8 N9 113.17(9) . . ? N7 C8 C1 122.51(10) . . ? N9 C8 C1 124.32(10) . . ? C7 C9 O1 110.58(12) . . ? C7 C9 H9 130.9(12) . . ? O1 C9 H9 118.5(12) . . ? O2 C10 N9 107.52(8) . . ? O2 C10 C11 107.90(8) . . ? N9 C10 C11 115.04(8) . . ? O2 C10 H10 110.6(9) . . ? N9 C10 H10 107.2(8) . . ? C11 C10 H10 108.6(8) . . ? O3 C11 C12 111.46(8) . . ? O3 C11 C10 107.22(8) . . ? C12 C11 C10 100.29(8) . . ? O3 C11 H11 112.0(9) . . ? C12 C11 H11 114.6(9) . . ? C10 C11 H11 110.4(9) . . ? O4 C12 C13 110.67(8) . . ? O4 C12 C11 115.33(8) . . ? C13 C12 C11 101.64(8) . . ? O4 C12 H12 109.4(8) . . ? C13 C12 H12 108.5(9) . . ? C11 C12 H12 110.9(9) . . ? O2 C13 C14 113.98(9) . . ? O2 C13 C12 102.35(8) . . ? C14 C13 C12 109.70(9) . . ? O2 C13 H13 110.3(8) . . ? C14 C13 H13 110.3(8) . . ? C12 C13 H13 109.8(8) . . ? O5 C14 C13 104.69(9) . . ? O5 C14 H14B 107.5(10) . . ? C13 C14 H14B 109.7(10) . . ? O5 C14 H14A 104.6(10) . . ? C13 C14 H14A 113.8(10) . . ? H14B C14 H14A 115.6(14) . . ? Si1 C15 H15C 108.2(14) . . ? Si1 C15 H15B 111(2) . . ? H15C C15 H15B 120(3) . . ? Si1 C15 H15A 109(2) . . ? H15C C15 H15A 105(2) . . ? H15B C15 H15A 102(3) . . ? Si1 C16 H16C 112.6(13) . . ? Si1 C16 H16B 106.5(15) . . ? H16C C16 H16B 105(2) . . ? Si1 C16 H16A 111.4(16) . . ? H16C C16 H16A 113(2) . . ? H16B C16 H16A 108(2) . . ? C19 C17 C18 110.7(2) . . ? C19 C17 C20 109.02(17) . . ? C18 C17 C20 108.54(18) . . ? C19 C17 Si1 108.79(15) . . ? C18 C17 Si1 109.70(16) . . ? C20 C17 Si1 110.04(11) . . ? C17 C18 H18C 111.1(16) . . ? C17 C18 H18B 107(2) . . ? H18C C18 H18B 103(2) . . ? C17 C18 H18A 121(3) . . ? H18C C18 H18A 103(4) . . ? H18B C18 H18A 111(4) . . ? C17 C19 H19C 108.7(13) . . ? C17 C19 H19B 102(3) . . ? H19C C19 H19B 110(3) . . ? C17 C19 H19A 112(2) . . ? H19C C19 H19A 117(3) . . ? H19B C19 H19A 106(3) . . ? C17 C20 H20C 111.0(17) . . ? C17 C20 H20B 116.0(13) . . ? H20C C20 H20B 107(2) . . ? C17 C20 H20A 110.5(19) . . ? H20C C20 H20A 103(2) . . ? H20B C20 H20A 108(2) . . ? C26 C21 C22 119.67(12) . . ? C26 C21 N2 121.98(11) . . ? C22 C21 N2 118.34(11) . . ? C23 C22 C21 119.63(13) . . ? C23 C22 H22 123.2(11) . . ? C21 C22 H22 117.0(11) . . ? C24 C23 C22 120.52(14) . . ? C24 C23 H23 120.9(12) . . ? C22 C23 H23 118.5(12) . . ? C25 C24 C23 119.88(13) . . ? C25 C24 H24 122.3(12) . . ? C23 C24 H24 117.6(12) . . ? C24 C25 C26 120.30(14) . . ? C24 C25 H25 121.7(12) . . ? C26 C25 H25 118.0(12) . . ? C21 C26 C25 119.98(13) . . ? C21 C26 H26 119.4(12) . . ? C25 C26 H26 120.6(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.256 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.038 data_8a _database_code_depnum_ccdc_archive 'CCDC 625283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Sp)-8-(2-Furyrl)adenosine-2'-O-(tert-butylmethylsilyl)-3',5'-cyclic N- benzylphosphoramidate ; _chemical_name_common ; (Sp)-8-(2-Furyrl)adenosine-2'-O-(tert-butylmethylsilyl)-3',5'- cyclic N-benzylphosphoramidate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H35 N6 O6 P Si' _chemical_formula_weight 598.67 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.8533(5) _cell_length_b 13.3879(6) _cell_length_c 20.9242(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3040.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57613 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 36.32 _reflns_number_total 14434 _reflns_number_gt 12632 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0512P)^2^+0.0869P] 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 refall _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 0.02(4) _refine_ls_number_reflns 14434 _refine_ls_number_parameters 510 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 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 Si1 Si 0.30692(2) 0.109087(17) 0.183038(11) 0.02075(5) Uani 1 1 d . . . P1 P 0.13027(2) 0.451660(17) 0.190727(10) 0.02256(4) Uani 1 1 d . . . O1 O 0.06590(8) -0.01569(5) -0.01547(3) 0.02941(15) Uani 1 1 d . . . O2 O 0.03103(6) 0.27346(5) 0.02713(3) 0.02346(12) Uani 1 1 d . . . O3 O 0.20459(6) 0.15124(5) 0.13009(3) 0.02233(11) Uani 1 1 d . . . O4 O 0.19509(7) 0.35102(5) 0.16694(3) 0.02352(12) Uani 1 1 d . . . O5 O -0.00398(7) 0.44774(6) 0.15978(3) 0.02855(14) Uani 1 1 d . . . O6 O 0.19874(8) 0.54332(5) 0.17503(3) 0.02984(14) Uani 1 1 d . . . N1 N 0.31876(8) 0.39386(6) -0.15422(4) 0.02556(14) Uani 1 1 d . . . N2 N 0.11099(9) 0.43430(7) 0.26610(4) 0.02874(16) Uani 1 1 d . . . H2A H 0.1223(16) 0.4861(13) 0.2919(8) 0.042(4) Uiso 1 1 d . . . N3 N 0.27643(8) 0.34878(6) -0.04444(4) 0.02456(14) Uani 1 1 d . . . N6 N 0.26416(10) 0.29352(7) -0.24104(4) 0.02967(17) Uani 1 1 d . . . H6A H 0.2263(16) 0.2422(13) -0.2556(7) 0.039(4) Uiso 1 1 d . . . H6B H 0.2822(17) 0.3453(14) -0.2661(8) 0.046(4) Uiso 1 1 d . . . N7 N 0.16138(7) 0.14923(6) -0.14225(3) 0.02183(13) Uani 1 1 d . . . N9 N 0.17003(7) 0.18815(5) -0.03675(3) 0.02014(12) Uani 1 1 d . . . C1 C 0.05351(9) 0.03474(6) -0.07207(4) 0.02233(14) Uani 1 1 d . . . C2 C 0.31969(9) 0.40808(7) -0.09046(4) 0.02636(16) Uani 1 1 d . . . H2B H 0.3587(13) 0.4687(10) -0.0759(7) 0.025(3) Uiso 1 1 d . . . C3 C -0.03522(11) -0.00800(8) -0.10858(5) 0.0337(2) Uani 1 1 d . . . H3 H -0.0618(15) 0.0123(13) -0.1513(8) 0.040(4) Uiso 1 1 d . . . C4 C 0.22740(8) 0.26501(6) -0.06922(4) 0.02051(13) Uani 1 1 d . . . C5 C 0.22152(8) 0.23951(6) -0.13343(4) 0.02071(14) Uani 1 1 d . . . C6 C 0.26849(8) 0.30906(6) -0.17754(4) 0.02259(14) Uani 1 1 d . . . C7 C -0.08117(12) -0.09066(9) -0.07254(6) 0.0389(2) Uani 1 1 d . . . H7 H -0.151(2) -0.1447(18) -0.0810(11) 0.076(7) Uiso 1 1 d . . . C8 C 0.12913(8) 0.12205(6) -0.08413(4) 0.01973(13) Uani 1 1 d . . . C9 C -0.01876(12) -0.09205(8) -0.01775(5) 0.0344(2) Uani 1 1 d . . . H9 H -0.0168(18) -0.1349(14) 0.0209(9) 0.050(5) Uiso 1 1 d . . . C10 C 0.12327(8) 0.19599(6) 0.02780(4) 0.01977(13) Uani 1 1 d . . . H10 H 0.0865(11) 0.1355(9) 0.0385(6) 0.016(3) Uiso 1 1 d . . . C11 C 0.21968(7) 0.22241(6) 0.08097(4) 0.01847(13) Uani 1 1 d . . . H11 H 0.3031(13) 0.2254(10) 0.0648(6) 0.022(3) Uiso 1 1 d . . . C12 C 0.17241(8) 0.32534(6) 0.10146(4) 0.01870(13) Uani 1 1 d . . . H12 H 0.2043(12) 0.3734(9) 0.0747(6) 0.020(3) Uiso 1 1 d . . . C13 C 0.03486(8) 0.31584(6) 0.08922(4) 0.02058(13) Uani 1 1 d . . . H13 H -0.0043(13) 0.2707(11) 0.1209(7) 0.028(3) Uiso 1 1 d . . . C14 C -0.02537(9) 0.41689(7) 0.09445(4) 0.02465(15) Uani 1 1 d . . . H14A H 0.0085(12) 0.4629(10) 0.0645(7) 0.025(3) Uiso 1 1 d . . . H14B H -0.1054(15) 0.4163(11) 0.0855(7) 0.030(3) Uiso 1 1 d . . . C15 C 0.41978(12) 0.20715(10) 0.20543(8) 0.0416(3) Uani 1 1 d . . . H15C H 0.373(2) 0.2624(17) 0.2289(10) 0.066(6) Uiso 1 1 d . . . H15B H 0.482(2) 0.1830(16) 0.2361(11) 0.068(6) Uiso 1 1 d . . . H15A H 0.462(2) 0.2208(17) 0.1725(11) 0.067(6) Uiso 1 1 d . . . C16 C 0.21269(12) 0.07122(9) 0.25294(5) 0.0359(2) Uani 1 1 d . . . H16C H 0.1802(19) 0.1296(16) 0.2750(9) 0.056(5) Uiso 1 1 d . . . H16B H 0.259(2) 0.0348(17) 0.2844(11) 0.078(7) Uiso 1 1 d . . . H16A H 0.136(2) 0.0237(19) 0.2406(12) 0.083(7) Uiso 1 1 d . . . C17 C 0.38871(10) -0.00220(8) 0.14665(5) 0.02913(18) Uani 1 1 d . . . C18 C 0.45965(17) 0.02836(12) 0.08635(7) 0.0525(4) Uani 1 1 d . . . H18C H 0.404(2) 0.0441(17) 0.0485(11) 0.070(6) Uiso 1 1 d . . . H18B H 0.5021(19) -0.0300(15) 0.0676(10) 0.062(6) Uiso 1 1 d . . . H18A H 0.515(2) 0.0862(19) 0.0917(12) 0.078(7) Uiso 1 1 d . . . C19 C 0.29441(14) -0.08300(9) 0.12905(8) 0.0440(3) Uani 1 1 d . . . H19C H 0.2322(18) -0.0599(14) 0.1016(9) 0.048(5) Uiso 1 1 d . . . H19B H 0.248(2) -0.1066(16) 0.1669(10) 0.064(6) Uiso 1 1 d . . . H19A H 0.333(2) -0.1406(18) 0.1083(11) 0.074(7) Uiso 1 1 d . . . C20 C 0.47931(13) -0.04673(12) 0.19542(7) 0.0459(3) Uani 1 1 d . . . H20C H 0.436(2) -0.0689(15) 0.2358(10) 0.059(5) Uiso 1 1 d . . . H20B H 0.518(2) -0.1042(16) 0.1809(10) 0.061(6) Uiso 1 1 d . . . H20A H 0.548(2) -0.0006(16) 0.2050(10) 0.066(6) Uiso 1 1 d . . . C21 C 0.03894(12) 0.35165(10) 0.29205(6) 0.0378(2) Uani 1 1 d . . . H21B H -0.0434(19) 0.3735(14) 0.3043(9) 0.051(5) Uiso 1 1 d . . . H21A H 0.0255(18) 0.2964(14) 0.2581(9) 0.052(5) Uiso 1 1 d . . . C22 C 0.09748(12) 0.30099(8) 0.34857(5) 0.0322(2) Uani 1 1 d . . . C23 C 0.21759(13) 0.32062(11) 0.36756(7) 0.0440(3) Uani 1 1 d . . . H23 H 0.266(2) 0.3734(17) 0.3408(10) 0.067(6) Uiso 1 1 d . . . C24 C 0.2697(2) 0.27024(17) 0.41922(10) 0.0694(5) Uani 1 1 d . . . H24 H 0.360(3) 0.276(2) 0.4311(14) 0.108(9) Uiso 1 1 d . . . C25 C 0.2027(3) 0.19949(14) 0.45200(9) 0.0741(6) Uani 1 1 d . . . H25 H 0.239(3) 0.155(2) 0.4856(14) 0.115(10) Uiso 1 1 d . . . C26 C 0.0833(3) 0.17957(10) 0.43398(8) 0.0691(7) Uani 1 1 d . . . H26 H 0.033(2) 0.1359(18) 0.4549(11) 0.075(7) Uiso 1 1 d . . . C27 C 0.02921(18) 0.22990(9) 0.38178(6) 0.0492(4) Uani 1 1 d . . . H27 H -0.051(2) 0.2141(17) 0.3690(10) 0.068(6) Uiso 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 Si1 0.02284(10) 0.02059(10) 0.01881(9) 0.00349(8) 0.00000(8) -0.00010(8) P1 0.02744(10) 0.02189(9) 0.01836(8) -0.00402(7) 0.00131(8) 0.00001(7) O1 0.0449(4) 0.0203(3) 0.0230(3) 0.0033(2) -0.0033(3) -0.0048(3) O2 0.0235(3) 0.0256(3) 0.0213(3) -0.0052(2) -0.0048(2) 0.0037(2) O3 0.0250(3) 0.0207(3) 0.0213(2) 0.0054(2) -0.0023(2) -0.0015(2) O4 0.0270(3) 0.0248(3) 0.0187(2) -0.0054(2) -0.0037(2) 0.0027(2) O5 0.0281(3) 0.0322(3) 0.0254(3) -0.0083(3) -0.0002(2) 0.0079(3) O6 0.0406(4) 0.0254(3) 0.0235(3) -0.0036(2) 0.0052(3) -0.0039(3) N1 0.0308(4) 0.0229(3) 0.0230(3) 0.0033(3) -0.0008(3) -0.0045(3) N2 0.0378(4) 0.0293(4) 0.0191(3) -0.0045(3) 0.0033(3) -0.0074(3) N3 0.0310(4) 0.0217(3) 0.0210(3) 0.0005(3) -0.0018(3) -0.0050(3) N6 0.0438(5) 0.0260(4) 0.0192(3) 0.0011(3) 0.0024(3) -0.0052(3) N7 0.0278(3) 0.0196(3) 0.0182(3) -0.0001(2) -0.0009(2) -0.0004(2) N9 0.0260(3) 0.0182(3) 0.0163(2) -0.0006(2) 0.0002(2) -0.0019(2) C1 0.0278(4) 0.0192(3) 0.0200(3) -0.0001(3) -0.0007(3) -0.0017(3) C2 0.0332(4) 0.0218(4) 0.0241(3) 0.0021(3) -0.0034(3) -0.0057(3) C3 0.0373(5) 0.0332(5) 0.0306(4) 0.0028(4) -0.0077(4) -0.0126(4) C4 0.0244(4) 0.0183(3) 0.0188(3) 0.0013(3) -0.0009(3) -0.0012(3) C5 0.0247(4) 0.0195(3) 0.0180(3) 0.0008(3) -0.0008(3) -0.0003(3) C6 0.0261(4) 0.0221(3) 0.0196(3) 0.0026(3) 0.0006(3) 0.0004(3) C7 0.0435(6) 0.0323(5) 0.0408(5) -0.0006(4) 0.0008(5) -0.0166(4) C8 0.0240(3) 0.0169(3) 0.0183(3) -0.0002(2) -0.0014(3) 0.0000(2) C9 0.0486(6) 0.0216(4) 0.0329(5) 0.0009(3) 0.0056(4) -0.0085(4) C10 0.0234(3) 0.0186(3) 0.0173(3) -0.0014(2) 0.0002(3) -0.0007(3) C11 0.0211(3) 0.0174(3) 0.0169(3) 0.0010(2) -0.0007(2) 0.0000(2) C12 0.0211(3) 0.0186(3) 0.0164(3) -0.0010(2) -0.0010(2) 0.0001(2) C13 0.0204(3) 0.0209(3) 0.0204(3) -0.0027(3) -0.0011(3) 0.0012(3) C14 0.0247(4) 0.0245(4) 0.0247(4) -0.0031(3) -0.0022(3) 0.0051(3) C15 0.0325(5) 0.0353(5) 0.0570(7) 0.0023(5) -0.0151(5) -0.0060(4) C16 0.0473(6) 0.0355(5) 0.0251(4) 0.0063(4) 0.0123(4) 0.0054(4) C17 0.0318(4) 0.0288(4) 0.0268(4) 0.0062(3) 0.0070(3) 0.0084(3) C18 0.0654(9) 0.0495(8) 0.0426(6) 0.0131(6) 0.0307(7) 0.0191(7) C19 0.0512(7) 0.0271(5) 0.0537(7) -0.0081(5) 0.0003(6) 0.0057(5) C20 0.0420(6) 0.0488(7) 0.0469(6) 0.0093(6) 0.0009(5) 0.0218(6) C21 0.0394(6) 0.0460(6) 0.0281(4) 0.0023(4) 0.0018(4) -0.0172(5) C22 0.0483(6) 0.0237(4) 0.0247(4) -0.0045(3) 0.0092(4) -0.0043(4) C23 0.0424(6) 0.0471(7) 0.0425(6) 0.0102(5) 0.0048(5) 0.0084(5) C24 0.0657(11) 0.0798(12) 0.0627(10) 0.0248(9) -0.0005(8) 0.0301(10) C25 0.1158(18) 0.0511(9) 0.0555(9) 0.0212(8) 0.0101(11) 0.0327(11) C26 0.140(2) 0.0208(5) 0.0467(8) 0.0036(5) 0.0328(10) -0.0016(8) C27 0.0858(11) 0.0280(5) 0.0338(5) -0.0079(4) 0.0181(6) -0.0219(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 Si1 O3 1.6671(7) . ? Si1 C16 1.8553(11) . ? Si1 C15 1.8557(12) . ? Si1 C17 1.8941(10) . ? P1 O6 1.4716(8) . ? P1 O5 1.5953(8) . ? P1 O4 1.5993(7) . ? P1 N2 1.6079(8) . ? O1 C1 1.3698(11) . ? O1 C9 1.3754(13) . ? O2 C13 1.4183(10) . ? O2 C10 1.4416(11) . ? O3 C11 1.4111(10) . ? O4 C12 1.4339(10) . ? O5 C14 1.4467(11) . ? N1 C2 1.3476(12) . ? N1 C6 1.3508(12) . ? N2 C21 1.4597(14) . ? N2 H2A 0.887(17) . ? N3 C2 1.3334(12) . ? N3 C4 1.3453(11) . ? N6 C6 1.3457(12) . ? N6 H6A 0.856(18) . ? N6 H6B 0.891(18) . ? N7 C8 1.3167(11) . ? N7 C5 1.3859(11) . ? N9 C4 1.3814(11) . ? N9 C8 1.4011(10) . ? N9 C10 1.4467(10) . ? C1 C3 1.3559(13) . ? C1 C8 1.4503(12) . ? C2 H2B 0.965(14) . ? C3 C7 1.4289(15) . ? C3 H3 0.979(17) . ? C4 C5 1.3878(12) . ? C5 C6 1.4066(12) . ? C7 C9 1.3318(18) . ? C7 H7 1.06(2) . ? C9 H9 0.992(18) . ? C10 C11 1.5677(11) . ? C10 H10 0.930(12) . ? C11 C12 1.5317(11) . ? C11 H11 0.967(14) . ? C12 C13 1.5201(12) . ? C12 H12 0.921(13) . ? C13 C14 1.5065(12) . ? C13 H13 0.993(14) . ? C14 H14A 0.952(14) . ? C14 H14B 0.889(16) . ? C15 H15C 1.02(2) . ? C15 H15B 0.99(2) . ? C15 H15A 0.85(2) . ? C16 H16C 0.97(2) . ? C16 H16B 0.96(2) . ? C16 H16A 1.08(3) . ? C17 C18 1.5336(15) . ? C17 C19 1.5341(18) . ? C17 C20 1.5376(16) . ? C18 H18C 1.02(2) . ? C18 H18B 0.99(2) . ? C18 H18A 0.99(3) . ? C19 H19C 0.940(19) . ? C19 H19B 0.99(2) . ? C19 H19A 0.98(2) . ? C20 H20C 1.01(2) . ? C20 H20B 0.93(2) . ? C20 H20A 0.99(2) . ? C21 C22 1.5040(17) . ? C21 H21B 0.98(2) . ? C21 H21A 1.036(19) . ? C22 C23 1.388(2) . ? C22 C27 1.3921(16) . ? C23 C24 1.394(2) . ? C23 H23 1.04(2) . ? C24 C25 1.377(3) . ? C24 H24 1.02(3) . ? C25 C26 1.376(4) . ? C25 H25 1.00(3) . ? C26 C27 1.411(3) . ? C26 H26 0.91(2) . ? C27 H27 0.93(2) . ? 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 O3 Si1 C16 104.43(5) . . ? O3 Si1 C15 111.59(5) . . ? C16 Si1 C15 110.98(7) . . ? O3 Si1 C17 108.14(4) . . ? C16 Si1 C17 111.12(5) . . ? C15 Si1 C17 110.40(6) . . ? O6 P1 O5 113.45(5) . . ? O6 P1 O4 114.26(4) . . ? O5 P1 O4 104.34(4) . . ? O6 P1 N2 113.90(4) . . ? O5 P1 N2 105.94(5) . . ? O4 P1 N2 103.93(4) . . ? C1 O1 C9 105.72(8) . . ? C13 O2 C10 104.98(6) . . ? C11 O3 Si1 129.44(6) . . ? C12 O4 P1 115.07(5) . . ? C14 O5 P1 122.65(6) . . ? C2 N1 C6 118.65(8) . . ? C21 N2 P1 122.96(7) . . ? C21 N2 H2A 116.2(11) . . ? P1 N2 H2A 117.7(11) . . ? C2 N3 C4 110.94(8) . . ? C6 N6 H6A 119.4(11) . . ? C6 N6 H6B 117.0(11) . . ? H6A N6 H6B 121.4(15) . . ? C8 N7 C5 104.08(7) . . ? C4 N9 C8 105.38(7) . . ? C4 N9 C10 124.28(7) . . ? C8 N9 C10 126.54(7) . . ? C3 C1 O1 110.41(8) . . ? C3 C1 C8 130.09(8) . . ? O1 C1 C8 119.49(8) . . ? N3 C2 N1 128.91(8) . . ? N3 C2 H2B 115.3(8) . . ? N1 C2 H2B 115.8(8) . . ? C1 C3 C7 106.11(9) . . ? C1 C3 H3 127.4(10) . . ? C7 C3 H3 126.5(10) . . ? N3 C4 N9 127.58(7) . . ? N3 C4 C5 126.61(8) . . ? N9 C4 C5 105.79(7) . . ? N7 C5 C4 111.41(7) . . ? N7 C5 C6 131.35(8) . . ? C4 C5 C6 117.11(8) . . ? N6 C6 N1 120.05(8) . . ? N6 C6 C5 122.19(8) . . ? N1 C6 C5 117.75(8) . . ? C9 C7 C3 106.71(10) . . ? C9 C7 H7 119.7(13) . . ? C3 C7 H7 133.6(13) . . ? N7 C8 N9 113.25(7) . . ? N7 C8 C1 122.28(7) . . ? N9 C8 C1 124.41(7) . . ? C7 C9 O1 111.05(9) . . ? C7 C9 H9 136.2(11) . . ? O1 C9 H9 112.8(11) . . ? O2 C10 N9 106.66(7) . . ? O2 C10 C11 107.94(6) . . ? N9 C10 C11 116.40(7) . . ? O2 C10 H10 109.3(8) . . ? N9 C10 H10 108.2(7) . . ? C11 C10 H10 108.1(7) . . ? O3 C11 C12 111.39(6) . . ? O3 C11 C10 106.68(6) . . ? C12 C11 C10 100.26(6) . . ? O3 C11 H11 113.0(8) . . ? C12 C11 H11 112.0(8) . . ? C10 C11 H11 112.7(8) . . ? O4 C12 C13 110.47(7) . . ? O4 C12 C11 115.20(7) . . ? C13 C12 C11 101.91(6) . . ? O4 C12 H12 110.4(8) . . ? C13 C12 H12 109.0(8) . . ? C11 C12 H12 109.5(8) . . ? O2 C13 C14 114.39(7) . . ? O2 C13 C12 102.51(6) . . ? C14 C13 C12 109.80(7) . . ? O2 C13 H13 110.8(8) . . ? C14 C13 H13 108.2(8) . . ? C12 C13 H13 111.1(8) . . ? O5 C14 C13 104.79(7) . . ? O5 C14 H14A 112.0(8) . . ? C13 C14 H14A 111.4(8) . . ? O5 C14 H14B 111.0(9) . . ? C13 C14 H14B 113.7(9) . . ? H14A C14 H14B 104.2(12) . . ? Si1 C15 H15C 107.9(12) . . ? Si1 C15 H15B 112.6(13) . . ? H15C C15 H15B 105.3(17) . . ? Si1 C15 H15A 107.7(15) . . ? H15C C15 H15A 120(2) . . ? H15B C15 H15A 103(2) . . ? Si1 C16 H16C 110.7(12) . . ? Si1 C16 H16B 113.0(15) . . ? H16C C16 H16B 105.8(17) . . ? Si1 C16 H16A 113.3(13) . . ? H16C C16 H16A 108.0(18) . . ? H16B C16 H16A 105.5(19) . . ? C18 C17 C19 109.00(12) . . ? C18 C17 C20 109.17(11) . . ? C19 C17 C20 108.21(10) . . ? C18 C17 Si1 110.87(8) . . ? C19 C17 Si1 109.79(8) . . ? C20 C17 Si1 109.75(8) . . ? C17 C18 H18C 113.4(13) . . ? C17 C18 H18B 110.5(12) . . ? H18C C18 H18B 97.6(16) . . ? C17 C18 H18A 114.9(14) . . ? H18C C18 H18A 106.6(18) . . ? H18B C18 H18A 112.5(18) . . ? C17 C19 H19C 113.2(11) . . ? C17 C19 H19B 111.8(13) . . ? H19C C19 H19B 103.4(17) . . ? C17 C19 H19A 112.4(14) . . ? H19C C19 H19A 107.0(17) . . ? H19B C19 H19A 108.5(18) . . ? C17 C20 H20C 111.6(12) . . ? C17 C20 H20B 113.2(13) . . ? H20C C20 H20B 104.1(17) . . ? C17 C20 H20A 112.1(12) . . ? H20C C20 H20A 111.5(17) . . ? H20B C20 H20A 103.8(18) . . ? N2 C21 C22 114.08(10) . . ? N2 C21 H21B 111.2(11) . . ? C22 C21 H21B 108.4(11) . . ? N2 C21 H21A 111.2(11) . . ? C22 C21 H21A 106.1(10) . . ? H21B C21 H21A 105.4(16) . . ? C23 C22 C27 119.11(13) . . ? C23 C22 C21 122.44(10) . . ? C27 C22 C21 118.42(12) . . ? C22 C23 C24 120.74(15) . . ? C22 C23 H23 116.4(12) . . ? C24 C23 H23 122.8(12) . . ? C25 C24 C23 120.4(2) . . ? C25 C24 H24 116.3(17) . . ? C23 C24 H24 122.9(17) . . ? C26 C25 C24 119.61(17) . . ? C26 C25 H25 117(2) . . ? C24 C25 H25 123(2) . . ? C25 C26 C27 120.74(15) . . ? C25 C26 H26 124.0(15) . . ? C27 C26 H26 115.3(16) . . ? C22 C27 C26 119.45(17) . . ? C22 C27 H27 120.5(14) . . ? C26 C27 H27 120.0(14) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.338 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.042