# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Arun Ghosh' 'Jorden Kass' _publ_contact_author_name 'Arun Ghosh' _publ_contact_author_email AKGHOSH@PURDUE.EDU _publ_section_title ; Highly Diastereoselective Synthesis of Modified Nucleosides via an Asymmetric Multicomponent Reaction ; # Attachment '2jk114.cif' data_2JK114 _database_code_depnum_ccdc_archive 'CCDC 757621' #TrackingRef '2jk114.cif' # 5. CRYSTAL DATA _chemical_compound_source ? _exptl_crystal_description needle _exptl_crystal_colour_primary colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _chemical_name_systematic ; ? ; _chemical_absolute_configuration ad _chemical_formula_sum 'C30 H37 F1 N2 O7 Si1' _chemical_formula_moiety 'C30 H37 F1 N2 O7 Si1' _chemical_formula_structural ? _chemical_formula_weight 584.72 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0216(4) _cell_length_b 16.7857(6) _cell_length_c 9.9119(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.502(3) _cell_angle_gamma 90.00 _cell_volume 1475.85(10) _cell_measurement_reflns_used 5198 _cell_measurement_theta_min 2 _cell_measurement_theta_max 72 _cell_formula_units_z 2 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' loop_ _atom_type_symbol _atom_type_radius_bond Si 1.11 F 0.72 O 0.73 N 0.75 C 0.77 H 0.32 _diffrn_radiation_type CU-K\a _diffrn_radiation_wavelength 1.54184 _exptl_absorpt_coefficient_mu 1.149 _cell_measurement_temperature 150(2) _exptl_crystal_F_000 620 # 6. DATA COLLECTION _diffrn_ambient__temperature 150(2) _diffrn_measurement_device_type Rigaku_Rapid_II _diffrn_radiation_monochromator 'confocal optics' _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt__process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.7757 _exptl_absorpt_correction_T_max 0.9121 _diffrn_reflns_number 16004 _diffrn_measured_fraction_theta_max 0.9470 _diffrn_reflns_theta_full 72.1 _diffrn_measured_fraction_theta_full 0.9470 _reflns_number_total 5138 _reflns_Friedel_coverage 0.8984 _reflns_number_gt 5103 _reflns_threshold_expression >2.0\s(I) _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 72.13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_max 12 _diffrn_special_details 'mosaicity from Denzo/Scalepack is 0.47' _diffrn_standards_number 0 _diffrn_standards_interval_time . _diffrn_standards_decay_% ? # 7. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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_R_factor_all 0.030 _refine_ls_R_factor_gt 0.030 _refine_ls_wR_factor_ref 0.080 _refine_ls_wR_factor_gt 0.079 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 5138 _refine_ls_number_parameters 383 _refine_ls_number_restraints 1 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_weighting_scheme 'calc ' _refine_ls_weighting_details '1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.3987P] where P=(Fo^2^+2Fc^2^)/3 ' _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.21 _refine_diff_density_min -0.16 _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _atom_type_scat_source 'International Tables for Crystallography (Vol C)' # 8. COMPUTING DATA _computing_data_collection 'CrystalClear(Rigaku, 2001)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1996)' _computing_structure_solution ; Direct methods (SIR2004, Burla et al., 2005) ; _computing_structure_refinement 'SHELX97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP (Johnson, 1976) PLATON (Spek, 1997) ; _computing_publication_material 'SHELX97(Sheldrick, 2008) and local programs' # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _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 Si5 0.89626(5) 0.10155(3) 0.67939(4) 0.02476(11) Uani 1 1 d . . . F25 0.70266(14) 0.32803(6) 0.42751(12) 0.0410(3) Uani 1 1 d . . . O1 0.43463(13) 0.07411(7) 0.41427(12) 0.0279(3) Uani 1 1 d . . . O22 0.30288(15) 0.16701(8) 0.06244(15) 0.0366(3) Uani 1 1 d . . . O24 0.53391(15) 0.40162(8) 0.19943(14) 0.0345(3) Uani 1 1 d . . . O31 0.47612(14) -0.04576(8) 0.08114(14) 0.0305(3) Uani 1 1 d . . . O32 0.72983(15) -0.13363(8) 0.10371(14) 0.0367(3) Uani 1 1 d . . . O33 0.87132(13) -0.03678(7) 0.21510(13) 0.0305(3) Uani 1 1 d . . . O51 0.73980(13) 0.07552(7) 0.57254(12) 0.0276(3) Uani 1 1 d . . . N21 0.48945(16) 0.16495(9) 0.25400(15) 0.0255(3) Uani 1 1 d . . . N23 0.42347(17) 0.28241(9) 0.13302(16) 0.0276(3) Uani 1 1 d . . . C2 0.46582(19) 0.07994(10) 0.27898(17) 0.0246(3) Uani 1 1 d . . . C3 0.60252(19) 0.02663(10) 0.27472(17) 0.0248(3) Uani 1 1 d . . . C4 0.5820(2) -0.03818(11) 0.37788(19) 0.0280(4) Uani 1 1 d . . . C5 0.5088(2) 0.00571(10) 0.48450(18) 0.0273(4) Uani 1 1 d . . . C22 0.39784(19) 0.20179(11) 0.14397(18) 0.0271(3) Uani 1 1 d . . . C24 0.5219(2) 0.33005(11) 0.22022(18) 0.0277(4) Uani 1 1 d . . . C25 0.6054(2) 0.28628(11) 0.33502(18) 0.0292(4) Uani 1 1 d . . . C26 0.58992(19) 0.20764(11) 0.34728(18) 0.0267(3) Uani 1 1 d . . . C31 0.61266(19) -0.00547(10) 0.13115(17) 0.0260(4) Uani 1 1 d . . . C32 0.7430(2) -0.06656(10) 0.14749(18) 0.0266(3) Uani 1 1 d . . . C34 1.0019(2) -0.09063(12) 0.2384(2) 0.0331(4) Uani 1 1 d . . . C35 1.1421(2) -0.04097(14) 0.2583(2) 0.0409(5) Uani 1 1 d . . . C36 0.6406(2) 0.06039(12) 0.03283(18) 0.0323(4) Uani 1 1 d . . . C50 0.6182(2) 0.03161(11) 0.61084(18) 0.0296(4) Uani 1 1 d . . . C51 1.0066(2) 0.01031(11) 0.75458(18) 0.0308(4) Uani 1 1 d . . . C52 0.9997(3) -0.05230(12) 0.6399(2) 0.0398(5) Uani 1 1 d . . . C53 0.9447(3) -0.02643(14) 0.8744(2) 0.0431(5) Uani 1 1 d . . . C54 1.1726(2) 0.03246(14) 0.8044(2) 0.0443(5) Uani 1 1 d . . . C511 0.8420(2) 0.17260(10) 0.80877(18) 0.0277(4) Uani 1 1 d . . . C512 0.9377(2) 0.19314(11) 0.93017(19) 0.0312(4) Uani 1 1 d . . . C513 0.8978(2) 0.25184(12) 1.0165(2) 0.0357(4) Uani 1 1 d . . . C514 0.7610(2) 0.29049(12) 0.9829(2) 0.0370(4) Uani 1 1 d . . . C515 0.6627(2) 0.27076(12) 0.8634(2) 0.0368(4) Uani 1 1 d . . . C516 0.7032(2) 0.21262(11) 0.77738(19) 0.0315(4) Uani 1 1 d . . . C521 1.0101(2) 0.15755(11) 0.5705(2) 0.0298(4) Uani 1 1 d . . . C522 1.1124(2) 0.21542(13) 0.6301(2) 0.0402(5) Uani 1 1 d . . . C523 1.2048(3) 0.25474(14) 0.5546(3) 0.0528(6) Uani 1 1 d . . . C524 1.1961(3) 0.23757(13) 0.4175(3) 0.0502(6) Uani 1 1 d . . . C525 1.0970(3) 0.17986(15) 0.3560(2) 0.0452(5) Uani 1 1 d . . . C526 1.0049(2) 0.14022(13) 0.4316(2) 0.0359(4) Uani 1 1 d . . . H2 0.3774 0.0600 0.2117 0.030 Uiso 1 1 calc R . . H3 0.6964 0.0573 0.3110 0.030 Uiso 1 1 calc R . . H5 0.4310 -0.0297 0.5131 0.033 Uiso 1 1 calc R . . H23 0.374(3) 0.3030(15) 0.064(2) 0.034(6) Uiso 1 1 d . . . H26 0.6498 0.1806 0.4222 0.032 Uiso 1 1 calc R . . H31 0.476(3) -0.0597(17) -0.004(3) 0.055(8) Uiso 1 1 d . . . H4A 0.6803 -0.0614 0.4207 0.034 Uiso 1 1 calc R . . H4B 0.5157 -0.0813 0.3332 0.034 Uiso 1 1 calc R . . H34A 0.9988 -0.1264 0.1585 0.040 Uiso 1 1 calc R . . H34B 1.0002 -0.1238 0.3207 0.040 Uiso 1 1 calc R . . H35A 1.1437 -0.0092 0.1757 0.061 Uiso 1 1 calc R . . H35B 1.2307 -0.0758 0.2753 0.061 Uiso 1 1 calc R . . H35C 1.1437 -0.0054 0.3370 0.061 Uiso 1 1 calc R . . H36A 0.6555 0.0367 -0.0541 0.048 Uiso 1 1 calc R . . H36B 0.7308 0.0905 0.0734 0.048 Uiso 1 1 calc R . . H36C 0.5535 0.0963 0.0160 0.048 Uiso 1 1 calc R . . H50A 0.5653 0.0652 0.6691 0.036 Uiso 1 1 calc R . . H50B 0.6583 -0.0158 0.6648 0.036 Uiso 1 1 calc R . . H512 1.0319 0.1667 0.9547 0.037 Uiso 1 1 calc R . . H513 0.9650 0.2653 1.0988 0.043 Uiso 1 1 calc R . . H514 0.7343 0.3306 1.0417 0.044 Uiso 1 1 calc R . . H515 0.5680 0.2969 0.8404 0.044 Uiso 1 1 calc R . . H516 0.6354 0.1995 0.6953 0.038 Uiso 1 1 calc R . . H522 1.1189 0.2281 0.7244 0.048 Uiso 1 1 calc R . . H523 1.2743 0.2936 0.5974 0.063 Uiso 1 1 calc R . . H524 1.2582 0.2653 0.3654 0.060 Uiso 1 1 calc R . . H525 1.0919 0.1674 0.2618 0.054 Uiso 1 1 calc R . . H526 0.9372 0.1006 0.3885 0.043 Uiso 1 1 calc R . . H52A 1.0366 -0.0287 0.5618 0.060 Uiso 1 1 calc R . . H52B 0.8953 -0.0700 0.6105 0.060 Uiso 1 1 calc R . . H52C 1.0629 -0.0980 0.6746 0.060 Uiso 1 1 calc R . . H53A 1.0052 -0.0731 0.9088 0.065 Uiso 1 1 calc R . . H53B 0.8397 -0.0426 0.8430 0.065 Uiso 1 1 calc R . . H53C 0.9496 0.0129 0.9481 0.065 Uiso 1 1 calc R . . H54A 1.1798 0.0727 0.8770 0.066 Uiso 1 1 calc R . . H54B 1.2148 0.0540 0.7276 0.066 Uiso 1 1 calc R . . H54C 1.2292 -0.0151 0.8405 0.066 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Si5 0.0240(2) 0.0263(2) 0.0237(2) 0.00048(17) 0.00369(16) -0.00145(17) F25 0.0466(7) 0.0320(6) 0.0383(6) -0.0109(5) -0.0085(5) -0.0026(5) O1 0.0278(6) 0.0280(6) 0.0286(6) 0.0026(5) 0.0068(5) 0.0030(5) O22 0.0343(7) 0.0335(7) 0.0361(7) 0.0002(5) -0.0096(6) 0.0007(5) O24 0.0419(7) 0.0261(7) 0.0360(7) -0.0006(5) 0.0081(6) 0.0044(5) O31 0.0265(6) 0.0357(7) 0.0278(7) -0.0040(5) 0.0008(5) -0.0053(5) O32 0.0349(7) 0.0290(7) 0.0420(7) 0.0008(5) -0.0039(6) -0.0087(6) O33 0.0227(6) 0.0298(7) 0.0380(7) -0.0008(5) 0.0027(5) -0.0077(5) O51 0.0270(6) 0.0309(6) 0.0249(6) -0.0033(5) 0.0051(5) 0.0002(5) N21 0.0251(7) 0.0233(7) 0.0265(7) -0.0002(5) 0.0009(6) 0.0009(5) N23 0.0291(8) 0.0261(7) 0.0260(8) 0.0029(6) 0.0003(6) 0.0031(6) C2 0.0241(8) 0.0236(8) 0.0256(8) -0.0012(6) 0.0034(6) -0.0003(6) C3 0.0237(8) 0.0237(8) 0.0260(8) -0.0021(6) 0.0019(6) -0.0015(7) C4 0.0283(8) 0.0256(9) 0.0290(9) -0.0008(7) 0.0029(7) 0.0016(7) C5 0.0262(9) 0.0260(8) 0.0297(9) -0.0017(7) 0.0050(7) 0.0032(7) C22 0.0258(8) 0.0270(9) 0.0276(8) 0.0027(6) 0.0028(7) 0.0014(7) C24 0.0288(8) 0.0266(9) 0.0288(9) 0.0010(7) 0.0080(7) 0.0014(7) C25 0.0290(9) 0.0277(9) 0.0297(9) -0.0043(7) 0.0021(7) -0.0019(7) C26 0.0244(8) 0.0293(9) 0.0248(8) -0.0003(6) 0.0000(6) 0.0007(7) C31 0.0237(8) 0.0262(9) 0.0270(8) -0.0025(6) 0.0016(7) -0.0009(7) C32 0.0283(8) 0.0273(9) 0.0242(8) -0.0036(7) 0.0049(7) -0.0016(6) C34 0.0251(9) 0.0354(10) 0.0376(10) 0.0028(7) 0.0026(8) -0.0031(8) C35 0.0240(9) 0.0467(12) 0.0511(12) -0.0007(8) 0.0044(8) -0.0089(10) C36 0.0376(10) 0.0319(9) 0.0285(9) 0.0014(8) 0.0092(7) 0.0015(7) C50 0.0299(9) 0.0356(10) 0.0240(8) -0.0019(7) 0.0067(7) 0.0016(7) C51 0.0305(10) 0.0303(9) 0.0308(9) 0.0052(7) 0.0032(7) -0.0027(7) C52 0.0467(11) 0.0323(10) 0.0400(11) 0.0078(8) 0.0071(9) -0.0050(8) C53 0.0502(12) 0.0429(12) 0.0361(11) 0.0160(9) 0.0075(9) 0.0106(9) C54 0.0307(10) 0.0443(12) 0.0541(13) 0.0086(8) -0.0021(9) -0.0054(10) C511 0.0301(9) 0.0260(8) 0.0280(9) -0.0002(7) 0.0081(7) 0.0010(7) C512 0.0294(9) 0.0326(10) 0.0307(9) 0.0013(7) 0.0035(7) -0.0020(7) C513 0.0425(11) 0.0341(10) 0.0303(9) -0.0016(8) 0.0062(8) -0.0049(8) C514 0.0493(12) 0.0278(9) 0.0374(10) 0.0004(8) 0.0168(9) -0.0054(8) C515 0.0366(10) 0.0342(10) 0.0411(11) 0.0099(8) 0.0112(9) 0.0016(8) C516 0.0313(9) 0.0319(9) 0.0305(9) 0.0038(7) 0.0040(7) 0.0004(7) C521 0.0270(9) 0.0289(9) 0.0338(10) 0.0032(7) 0.0066(7) 0.0014(7) C522 0.0415(11) 0.0352(10) 0.0479(11) -0.0082(9) 0.0185(9) -0.0090(9) C523 0.0541(14) 0.0360(11) 0.0757(17) -0.0121(10) 0.0317(12) -0.0111(11) C524 0.0535(14) 0.0367(12) 0.0701(16) 0.0010(10) 0.0373(12) 0.0077(10) C525 0.0487(12) 0.0514(13) 0.0404(11) 0.0091(10) 0.0213(10) 0.0098(10) C526 0.0329(10) 0.0423(11) 0.0329(10) 0.0024(8) 0.0071(8) 0.0032(8) # 10. MOLECULAR GEOMETRY _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si5 O51 1.6613(13) . . ? Si5 C521 1.8724(19) . . ? Si5 C511 1.8802(18) . . ? Si5 C51 1.9031(19) . . ? F25 C25 1.345(2) . . ? O1 C2 1.423(2) . . ? O1 C5 1.442(2) . . ? O22 C22 1.215(2) . . ? O24 C24 1.227(2) . . ? O31 C31 1.413(2) . . ? O31 H31 0.88(3) . . ? O32 C32 1.205(2) . . ? O33 C32 1.325(2) . . ? O33 C34 1.469(2) . . ? O51 C50 1.429(2) . . ? N21 C26 1.373(2) . . ? N21 C22 1.388(2) . . ? N21 C2 1.470(2) . . ? N23 C24 1.377(2) . . ? N23 C22 1.381(2) . . ? N23 H23 0.83(2) . . ? C2 C3 1.531(2) . . ? C2 H2 1.0000 . . ? C3 C4 1.527(2) . . ? C3 C31 1.540(2) . . ? C3 H3 1.0000 . . ? C4 C5 1.533(2) . . ? C4 H4A 0.9900 . . ? C4 H4B 0.9900 . . ? C5 C50 1.510(2) . . ? C5 H5 1.0000 . . ? C24 C25 1.446(3) . . ? C25 C26 1.335(3) . . ? C26 H26 0.9500 . . ? C31 C36 1.525(2) . . ? C31 C32 1.546(2) . . ? C34 C35 1.498(3) . . ? C34 H34A 0.9900 . . ? C34 H34B 0.9900 . . ? C35 H35A 0.9800 . . ? C35 H35B 0.9800 . . ? C35 H35C 0.9800 . . ? C36 H36A 0.9800 . . ? C36 H36B 0.9800 . . ? C36 H36C 0.9800 . . ? C50 H50A 0.9900 . . ? C50 H50B 0.9900 . . ? C51 C53 1.531(3) . . ? C51 C54 1.535(3) . . ? C51 C52 1.541(3) . . ? C52 H52A 0.9800 . . ? C52 H52B 0.9800 . . ? C52 H52C 0.9800 . . ? C53 H53A 0.9800 . . ? C53 H53B 0.9800 . . ? C53 H53C 0.9800 . . ? C54 H54A 0.9800 . . ? C54 H54B 0.9800 . . ? C54 H54C 0.9800 . . ? C511 C512 1.391(3) . . ? C511 C516 1.405(3) . . ? C512 C513 1.395(3) . . ? C512 H512 0.9500 . . ? C513 C514 1.380(3) . . ? C513 H513 0.9500 . . ? C514 C515 1.384(3) . . ? C514 H514 0.9500 . . ? C515 C516 1.388(3) . . ? C515 H515 0.9500 . . ? C516 H516 0.9500 . . ? C521 C522 1.395(3) . . ? C521 C526 1.400(3) . . ? C522 C523 1.385(3) . . ? C522 H522 0.9500 . . ? C523 C524 1.377(4) . . ? C523 H523 0.9500 . . ? C524 C525 1.383(4) . . ? C524 H524 0.9500 . . ? C525 C526 1.386(3) . . ? C525 H525 0.9500 . . ? C526 H526 0.9500 . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O51 Si5 C521 104.84(7) . . . ? O51 Si5 C511 107.76(7) . . . ? C521 Si5 C511 108.23(8) . . . ? O51 Si5 C51 111.17(8) . . . ? C521 Si5 C51 109.09(8) . . . ? C511 Si5 C51 115.21(8) . . . ? C2 O1 C5 110.82(12) . . . ? C31 O31 H31 108.3(18) . . . ? C32 O33 C34 116.67(13) . . . ? C50 O51 Si5 124.77(10) . . . ? C26 N21 C22 121.48(14) . . . ? C26 N21 C2 119.43(14) . . . ? C22 N21 C2 118.74(14) . . . ? C24 N23 C22 128.18(16) . . . ? C24 N23 H23 118.0(17) . . . ? C22 N23 H23 113.8(17) . . . ? O1 C2 N21 106.57(13) . . . ? O1 C2 C3 106.53(13) . . . ? N21 C2 C3 114.86(14) . . . ? O1 C2 H2 109.60 . . . ? N21 C2 H2 109.60 . . . ? C3 C2 H2 109.60 . . . ? C4 C3 C2 101.61(13) . . . ? C4 C3 C31 113.85(14) . . . ? C2 C3 C31 114.46(14) . . . ? C4 C3 H3 108.90 . . . ? C2 C3 H3 108.90 . . . ? C31 C3 H3 108.90 . . . ? C3 C4 C5 103.84(14) . . . ? C3 C4 H4A 111.00 . . . ? C5 C4 H4A 111.00 . . . ? C3 C4 H4B 111.00 . . . ? C5 C4 H4B 111.00 . . . ? H4A C4 H4B 109.00 . . . ? O1 C5 C50 110.28(14) . . . ? O1 C5 C4 105.67(13) . . . ? C50 C5 C4 114.30(15) . . . ? O1 C5 H5 108.80 . . . ? C50 C5 H5 108.80 . . . ? C4 C5 H5 108.80 . . . ? O22 C22 N23 121.78(16) . . . ? O22 C22 N21 123.74(16) . . . ? N23 C22 N21 114.47(15) . . . ? O24 C24 N23 121.99(16) . . . ? O24 C24 C25 125.49(17) . . . ? N23 C24 C25 112.52(15) . . . ? C26 C25 F25 121.29(17) . . . ? C26 C25 C24 121.72(16) . . . ? F25 C25 C24 116.97(16) . . . ? C25 C26 N21 121.47(16) . . . ? C25 C26 H26 119.30 . . . ? N21 C26 H26 119.30 . . . ? O31 C31 C36 110.96(15) . . . ? O31 C31 C3 107.26(13) . . . ? C36 C31 C3 112.42(14) . . . ? O31 C31 C32 108.48(13) . . . ? C36 C31 C32 109.68(14) . . . ? C3 C31 C32 107.90(14) . . . ? O32 C32 O33 123.66(17) . . . ? O32 C32 C31 123.98(16) . . . ? O33 C32 C31 112.36(14) . . . ? O33 C34 C35 108.18(15) . . . ? O33 C34 H34A 110.10 . . . ? C35 C34 H34A 110.10 . . . ? O33 C34 H34B 110.10 . . . ? C35 C34 H34B 110.10 . . . ? H34A C34 H34B 108.40 . . . ? C34 C35 H35A 109.50 . . . ? C34 C35 H35B 109.50 . . . ? H35A C35 H35B 109.50 . . . ? C34 C35 H35C 109.50 . . . ? H35A C35 H35C 109.50 . . . ? H35B C35 H35C 109.50 . . . ? C31 C36 H36A 109.50 . . . ? C31 C36 H36B 109.50 . . . ? H36A C36 H36B 109.50 . . . ? C31 C36 H36C 109.50 . . . ? H36A C36 H36C 109.50 . . . ? H36B C36 H36C 109.50 . . . ? O51 C50 C5 110.21(13) . . . ? O51 C50 H50A 109.60 . . . ? C5 C50 H50A 109.60 . . . ? O51 C50 H50B 109.60 . . . ? C5 C50 H50B 109.60 . . . ? H50A C50 H50B 108.10 . . . ? C53 C51 C54 108.69(17) . . . ? C53 C51 C52 109.02(17) . . . ? C54 C51 C52 107.97(16) . . . ? C53 C51 Si5 112.89(13) . . . ? C54 C51 Si5 109.96(14) . . . ? C52 C51 Si5 108.20(13) . . . ? C51 C52 H52A 109.50 . . . ? C51 C52 H52B 109.50 . . . ? H52A C52 H52B 109.50 . . . ? C51 C52 H52C 109.50 . . . ? H52A C52 H52C 109.50 . . . ? H52B C52 H52C 109.50 . . . ? C51 C53 H53A 109.50 . . . ? C51 C53 H53B 109.50 . . . ? H53A C53 H53B 109.50 . . . ? C51 C53 H53C 109.50 . . . ? H53A C53 H53C 109.50 . . . ? H53B C53 H53C 109.50 . . . ? C51 C54 H54A 109.50 . . . ? C51 C54 H54B 109.50 . . . ? H54A C54 H54B 109.50 . . . ? C51 C54 H54C 109.50 . . . ? H54A C54 H54C 109.50 . . . ? H54B C54 H54C 109.50 . . . ? C512 C511 C516 117.44(16) . . . ? C512 C511 Si5 123.35(14) . . . ? C516 C511 Si5 118.98(14) . . . ? C511 C512 C513 121.13(18) . . . ? C511 C512 H512 119.40 . . . ? C513 C512 H512 119.40 . . . ? C514 C513 C512 120.24(18) . . . ? C514 C513 H513 119.90 . . . ? C512 C513 H513 119.90 . . . ? C513 C514 C515 119.95(18) . . . ? C513 C514 H514 120.00 . . . ? C515 C514 H514 120.00 . . . ? C514 C515 C516 119.64(18) . . . ? C514 C515 H515 120.20 . . . ? C516 C515 H515 120.20 . . . ? C515 C516 C511 121.60(18) . . . ? C515 C516 H516 119.20 . . . ? C511 C516 H516 119.20 . . . ? C522 C521 C526 117.53(18) . . . ? C522 C521 Si5 119.72(15) . . . ? C526 C521 Si5 122.61(14) . . . ? C523 C522 C521 121.3(2) . . . ? C523 C522 H522 119.30 . . . ? C521 C522 H522 119.30 . . . ? C524 C523 C522 120.1(2) . . . ? C524 C523 H523 119.90 . . . ? C522 C523 H523 119.90 . . . ? C523 C524 C525 119.9(2) . . . ? C523 C524 H524 120.10 . . . ? C525 C524 H524 120.10 . . . ? C524 C525 C526 120.1(2) . . . ? C524 C525 H525 120.00 . . . ? C526 C525 H525 120.00 . . . ? C525 C526 C521 121.1(2) . . . ? C525 C526 H526 119.50 . . . ? C521 C526 H526 119.50 . . . ? 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 C521 Si5 O51 C50 -179.71(13) . . . . ? C511 Si5 O51 C50 -64.58(15) . . . . ? C51 Si5 O51 C50 62.55(15) . . . . ? C5 O1 C2 N21 -139.72(14) . . . . ? C5 O1 C2 C3 -16.64(17) . . . . ? C26 N21 C2 O1 51.54(19) . . . . ? C22 N21 C2 O1 -121.76(15) . . . . ? C26 N21 C2 C3 -66.18(19) . . . . ? C22 N21 C2 C3 120.52(17) . . . . ? O1 C2 C3 C4 30.84(16) . . . . ? N21 C2 C3 C4 148.58(14) . . . . ? O1 C2 C3 C31 153.99(13) . . . . ? N21 C2 C3 C31 -88.27(17) . . . . ? C2 C3 C4 C5 -32.89(17) . . . . ? C31 C3 C4 C5 -156.46(14) . . . . ? C2 O1 C5 C50 119.12(14) . . . . ? C2 O1 C5 C4 -4.88(17) . . . . ? C3 C4 C5 O1 24.24(17) . . . . ? C3 C4 C5 C50 -97.20(17) . . . . ? C24 N23 C22 O22 177.01(17) . . . . ? C24 N23 C22 N21 -3.4(3) . . . . ? C26 N21 C22 O22 -176.68(17) . . . . ? C2 N21 C22 O22 -3.5(3) . . . . ? C26 N21 C22 N23 3.7(2) . . . . ? C2 N21 C22 N23 176.87(15) . . . . ? C22 N23 C24 O24 -179.62(17) . . . . ? C22 N23 C24 C25 0.2(3) . . . . ? O24 C24 C25 C26 -177.32(18) . . . . ? N23 C24 C25 C26 2.9(2) . . . . ? O24 C24 C25 F25 1.0(3) . . . . ? N23 C24 C25 F25 -178.80(15) . . . . ? F25 C25 C26 N21 179.19(16) . . . . ? C24 C25 C26 N21 -2.5(3) . . . . ? C22 N21 C26 C25 -1.0(3) . . . . ? C2 N21 C26 C25 -174.12(17) . . . . ? C4 C3 C31 O31 60.48(18) . . . . ? C2 C3 C31 O31 -55.80(18) . . . . ? C4 C3 C31 C36 -177.27(15) . . . . ? C2 C3 C31 C36 66.44(19) . . . . ? C4 C3 C31 C32 -56.20(18) . . . . ? C2 C3 C31 C32 -172.49(14) . . . . ? C34 O33 C32 O32 -1.2(2) . . . . ? C34 O33 C32 C31 178.93(14) . . . . ? O31 C31 C32 O32 10.6(2) . . . . ? C36 C31 C32 O32 -110.70(19) . . . . ? C3 C31 C32 O32 126.53(18) . . . . ? O31 C31 C32 O33 -169.47(14) . . . . ? C36 C31 C32 O33 69.19(19) . . . . ? C3 C31 C32 O33 -53.57(18) . . . . ? C32 O33 C34 C35 156.01(16) . . . . ? Si5 O51 C50 C5 -169.62(12) . . . . ? O1 C5 C50 O51 -66.75(18) . . . . ? C4 C5 C50 O51 52.1(2) . . . . ? O51 Si5 C51 C53 -80.64(15) . . . . ? C521 Si5 C51 C53 164.23(14) . . . . ? C511 Si5 C51 C53 42.31(17) . . . . ? O51 Si5 C51 C54 157.80(13) . . . . ? C521 Si5 C51 C54 42.67(16) . . . . ? C511 Si5 C51 C54 -79.25(15) . . . . ? O51 Si5 C51 C52 40.10(15) . . . . ? C521 Si5 C51 C52 -75.03(15) . . . . ? C511 Si5 C51 C52 163.06(13) . . . . ? O51 Si5 C511 C512 165.61(15) . . . . ? C521 Si5 C511 C512 -81.52(17) . . . . ? C51 Si5 C511 C512 40.86(18) . . . . ? O51 Si5 C511 C516 -20.03(16) . . . . ? C521 Si5 C511 C516 92.85(16) . . . . ? C51 Si5 C511 C516 -144.77(15) . . . . ? C516 C511 C512 C513 -0.7(3) . . . . ? Si5 C511 C512 C513 173.78(15) . . . . ? C511 C512 C513 C514 0.4(3) . . . . ? C512 C513 C514 C515 0.3(3) . . . . ? C513 C514 C515 C516 -0.6(3) . . . . ? C514 C515 C516 C511 0.3(3) . . . . ? C512 C511 C516 C515 0.3(3) . . . . ? Si5 C511 C516 C515 -174.37(15) . . . . ? O51 Si5 C521 C522 152.69(15) . . . . ? C511 Si5 C521 C522 37.89(18) . . . . ? C51 Si5 C521 C522 -88.16(17) . . . . ? O51 Si5 C521 C526 -31.81(17) . . . . ? C511 Si5 C521 C526 -146.61(15) . . . . ? C51 Si5 C521 C526 87.34(17) . . . . ? C526 C521 C522 C523 0.5(3) . . . . ? Si5 C521 C522 C523 176.19(18) . . . . ? C521 C522 C523 C524 0.5(4) . . . . ? C522 C523 C524 C525 -1.2(4) . . . . ? C523 C524 C525 C526 0.9(3) . . . . ? C524 C525 C526 C521 0.0(3) . . . . ? C522 C521 C526 C525 -0.7(3) . . . . ? Si5 C521 C526 C525 -176.33(16) . . . . ?