# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Fuchs, Philip' _publ_contact_author_email pfuchs@purdue.edu loop_ _publ_author_name 'Philip Fuchs' 'Vikas Sikervar' 'James C. Fleet' data_BOC _database_code_depnum_ccdc_archive 'CCDC 879401' #TrackingRef '- vikas boc.cif' # 5. CRYSTAL DATA _chemical_compound_source ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _chemical_name_systematic ; ? ; _chemical_absolute_configuration ad _chemical_formula_sum 'C24 H38 O6 S1 Si1' _chemical_formula_moiety 'C24 H38 O6 S1 Si1' _chemical_formula_structural ? _chemical_formula_weight 482.72 _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 12.3827(5) _cell_length_b 6.2563(3) _cell_length_c 16.7955(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.199(9) _cell_angle_gamma 90.00 _cell_volume 1300.19(12) _cell_measurement_reflns_used 4246 _cell_measurement_theta_min 2 _cell_measurement_theta_max 66 _cell_formula_units_z 2 _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' loop_ _atom_type_symbol _atom_type_radius_bond S 1.02 Si 1.11 O 0.73 C 0.77 H 0.32 _diffrn_radiation_type CU-K\a _diffrn_radiation_wavelength 1.54184 _exptl_absorpt_coefficient_mu 1.812 _cell_measurement_temperature 150.0(2) _exptl_crystal_F_000 520 # 6. DATA COLLECTION _diffrn_ambient_temperature 150.0(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 0.6903 _exptl_absorpt_correction_T_max 0.9644 _diffrn_reflns_number 13412 _diffrn_measured_fraction_theta_max 0.9660 _diffrn_reflns_theta_full 60.0 _diffrn_measured_fraction_theta_full 0.9660 _reflns_number_total 3639 _reflns_Friedel_coverage 1.0000 _reflns_number_gt 3362 _reflns_threshold_expression >2.0\s(I) _diffrn_reflns_av_R_equivalents 0.0890 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 66.58 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_max 19 _diffrn_special_details 'mosaicity from Denzo/Scalepack is 1.39' _diffrn_standards_number 0 _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_measurement_details ; Data were collected on a Rigaku Rapid which has a quarter chi circle and a 200 degree curved image plate at a fixed distance of 127.4mm. Strategy was optimized using the CrystalClear software. The completeness is the best that can be obtained with this geometry. The missing data are not cusp data but mostly high angle data. Also the use of HKL2000/SCALEPACK lowers the number of observed data as inconsistent equivalents are removed from the data set and not included in the collected total ; # 7. REFINEMENT DATA _refine_special_details ; Outlier data were removed using a local program based on the method of Prince and Nicholson. 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 0.073 _refine_ls_R_factor_gt 0.068 _refine_ls_wR_factor_ref 0.178 _refine_ls_wR_factor_gt 0.173 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3639 _refine_ls_d_res_high 0.89 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_weighting_scheme 'calc ' _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+1.3724P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.45 _refine_diff_density_min -0.37 _refine_ls_extinction_method 'SHELXL97 (Sheldrick 2008)' _refine_ls_extinction_coef 0.50E-03 _refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _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, 2003) ; _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 S1 0.71278(10) -0.1603(2) 0.08658(8) 0.0518(4) Uani 1 1 d . . . Si1 1.05028(12) 0.4682(2) 0.28718(9) 0.0511(4) Uani 1 1 d . . . O1 0.6237(3) -0.1445(8) 0.1377(2) 0.0656(11) Uani 1 1 d . . . O2 0.7891(3) -0.3307(6) 0.0987(2) 0.0635(11) Uani 1 1 d . . . O3 1.0080(3) 0.2490(6) 0.2411(2) 0.0525(9) Uani 1 1 d . . . O4 0.7255(3) 0.2876(6) 0.2412(2) 0.0515(9) Uani 1 1 d . . . O5 0.6214(3) 0.5137(6) 0.2961(2) 0.0546(9) Uani 1 1 d . . . O6 0.7079(3) 0.2681(7) 0.3741(2) 0.0638(11) Uani 1 1 d . . . C1 0.7872(4) 0.0901(9) 0.0929(3) 0.0474(12) Uani 1 1 d . . . C2 0.8566(4) 0.0845(8) 0.1711(3) 0.0454(11) Uani 1 1 d . . . C3 0.9465(4) 0.2501(9) 0.1674(3) 0.0477(12) Uani 1 1 d . . . C4 1.1332(4) 0.3704(11) 0.3767(3) 0.0544(13) Uani 1 1 d . . . C5 1.1826(5) 0.5653(11) 0.4201(4) 0.0646(16) Uani 1 1 d . . . C6 1.2233(5) 0.2250(11) 0.3486(4) 0.0662(16) Uani 1 1 d . . . C7 1.0619(5) 0.2469(12) 0.4325(4) 0.0710(17) Uani 1 1 d . . . C8 1.1326(5) 0.6330(11) 0.2185(4) 0.0694(17) Uani 1 1 d . . . C9 0.9320(5) 0.6294(11) 0.3171(4) 0.0648(15) Uani 1 1 d . . . C10 1.0193(4) 0.1965(9) 0.0994(3) 0.0531(13) Uani 1 1 d . . . C11 0.9558(4) 0.1661(8) 0.0231(3) 0.0511(13) Uani 1 1 d . . . C12 0.8516(4) 0.1229(9) 0.0202(3) 0.0499(12) Uani 1 1 d . . . C13 0.7923(4) 0.0987(10) 0.2460(3) 0.0501(12) Uani 1 1 d . . . C14 0.6867(4) 0.3503(10) 0.3108(3) 0.0511(12) Uani 1 1 d . . . C15 0.5691(4) 0.6238(10) 0.3629(3) 0.0573(14) Uani 1 1 d . . . C16 0.4991(5) 0.4683(13) 0.4074(4) 0.0714(17) Uani 1 1 d . . . C17 0.5016(5) 0.7910(12) 0.3200(4) 0.0734(19) Uani 1 1 d . . . C18 0.6555(5) 0.7263(11) 0.4160(4) 0.0660(16) Uani 1 1 d . . . C19 0.6594(4) -0.1845(9) -0.0123(3) 0.0487(12) Uani 1 1 d . . . C20 0.5779(5) -0.0492(10) -0.0404(3) 0.0577(14) Uani 1 1 d . . . C21 0.5323(5) -0.0757(10) -0.1156(4) 0.0612(16) Uani 1 1 d . . . C22 0.5657(5) -0.2466(11) -0.1615(4) 0.0674(16) Uani 1 1 d . . . C23 0.6471(5) -0.3803(11) -0.1335(4) 0.0637(15) Uani 1 1 d . . . C24 0.6933(4) -0.3510(10) -0.0591(4) 0.0564(14) Uani 1 1 d . . . H1 0.7340 0.2098 0.0962 0.057 Uiso 1 1 calc R . . H2 0.8929 -0.0582 0.1727 0.054 Uiso 1 1 calc R . . H3 0.9141 0.3949 0.1584 0.057 Uiso 1 1 calc R . . H11 0.9920 0.1782 -0.0255 0.061 Uiso 1 1 calc R . . H12 0.8155 0.1121 -0.0306 0.060 Uiso 1 1 calc R . . H20 0.5533 0.0627 -0.0074 0.069 Uiso 1 1 calc R . . H21 0.4789 0.0210 -0.1359 0.073 Uiso 1 1 calc R . . H22 0.5322 -0.2714 -0.2125 0.081 Uiso 1 1 calc R . . H23 0.6712 -0.4934 -0.1661 0.076 Uiso 1 1 calc R . . H24 0.7486 -0.4448 -0.0397 0.068 Uiso 1 1 calc R . . H5A 1.2178 0.5195 0.4705 0.097 Uiso 1 1 calc R . . H5B 1.1254 0.6684 0.4309 0.097 Uiso 1 1 calc R . . H5C 1.2361 0.6324 0.3866 0.097 Uiso 1 1 calc R . . H6A 1.2672 0.1756 0.3948 0.099 Uiso 1 1 calc R . . H6B 1.2689 0.3046 0.3126 0.099 Uiso 1 1 calc R . . H6C 1.1914 0.1015 0.3205 0.099 Uiso 1 1 calc R . . H7A 1.0261 0.1296 0.4032 0.106 Uiso 1 1 calc R . . H7B 1.0073 0.3430 0.4534 0.106 Uiso 1 1 calc R . . H7C 1.1065 0.1886 0.4768 0.106 Uiso 1 1 calc R . . H8A 1.1972 0.5527 0.2045 0.104 Uiso 1 1 calc R . . H8B 1.1544 0.7663 0.2452 0.104 Uiso 1 1 calc R . . H8C 1.0893 0.6659 0.1700 0.104 Uiso 1 1 calc R . . H9A 0.8795 0.6397 0.2721 0.097 Uiso 1 1 calc R . . H9B 0.9562 0.7730 0.3327 0.097 Uiso 1 1 calc R . . H9C 0.8981 0.5602 0.3621 0.097 Uiso 1 1 calc R . . H10A 1.0721 0.3136 0.0930 0.064 Uiso 1 1 calc R . . H10B 1.0601 0.0642 0.1124 0.064 Uiso 1 1 calc R . . H13A 0.7465 -0.0300 0.2509 0.060 Uiso 1 1 calc R . . H13B 0.8420 0.1066 0.2935 0.060 Uiso 1 1 calc R . . H16A 0.4534 0.3876 0.3691 0.107 Uiso 1 1 calc R . . H16B 0.4533 0.5478 0.4434 0.107 Uiso 1 1 calc R . . H16C 0.5454 0.3692 0.4383 0.107 Uiso 1 1 calc R . . H17A 0.5486 0.8854 0.2902 0.110 Uiso 1 1 calc R . . H17B 0.4627 0.8753 0.3589 0.110 Uiso 1 1 calc R . . H17C 0.4496 0.7213 0.2830 0.110 Uiso 1 1 calc R . . H18A 0.7003 0.6148 0.4416 0.099 Uiso 1 1 calc R . . H18B 0.6215 0.8121 0.4570 0.099 Uiso 1 1 calc R . . H18C 0.7008 0.8185 0.3840 0.099 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 S1 0.0436(7) 0.0536(8) 0.0580(7) -0.0049(6) -0.0006(6) 0.0032(6) Si1 0.0432(8) 0.0534(9) 0.0564(8) -0.0012(7) -0.0026(6) 0.0015(7) O1 0.052(2) 0.078(3) 0.067(2) -0.021(2) 0.0076(18) -0.002(2) O2 0.061(2) 0.055(2) 0.073(2) -0.007(2) -0.018(2) 0.0043(19) O3 0.042(2) 0.058(2) 0.057(2) 0.0020(17) -0.0015(16) 0.0063(18) O4 0.044(2) 0.060(2) 0.0509(19) 0.0080(17) 0.0033(16) -0.0013(16) O5 0.048(2) 0.063(2) 0.053(2) 0.0103(18) 0.0023(16) -0.0037(18) O6 0.067(3) 0.070(3) 0.056(2) 0.012(2) 0.0106(19) 0.008(2) C1 0.043(3) 0.044(3) 0.055(3) 0.002(2) -0.001(2) 0.001(2) C2 0.041(3) 0.041(3) 0.053(3) 0.003(2) 0.003(2) -0.002(2) C3 0.041(3) 0.049(3) 0.052(3) 0.004(2) -0.004(2) 0.004(2) C4 0.045(3) 0.066(4) 0.053(3) -0.001(3) -0.002(2) 0.000(3) C5 0.051(3) 0.072(4) 0.070(4) 0.006(3) -0.010(3) -0.003(3) C6 0.056(3) 0.074(4) 0.067(4) 0.006(3) -0.007(3) -0.009(3) C7 0.065(4) 0.083(4) 0.064(4) -0.003(3) 0.001(3) 0.007(3) C8 0.074(4) 0.068(4) 0.067(4) -0.017(3) 0.007(3) 0.000(3) C9 0.059(4) 0.060(4) 0.074(4) 0.004(3) -0.012(3) -0.003(3) C10 0.043(3) 0.047(3) 0.070(3) -0.001(2) 0.006(2) 0.005(3) C11 0.051(3) 0.047(3) 0.056(3) -0.001(3) 0.006(2) -0.001(2) C12 0.045(3) 0.048(3) 0.057(3) -0.002(3) 0.002(2) 0.001(3) C13 0.040(3) 0.056(3) 0.054(3) 0.002(3) -0.003(2) 0.001(3) C14 0.038(3) 0.060(3) 0.054(3) -0.009(3) -0.001(2) -0.002(3) C15 0.046(3) 0.065(4) 0.062(3) 0.003(3) 0.010(3) -0.007(3) C16 0.049(3) 0.081(4) 0.086(4) -0.004(3) 0.022(3) -0.002(4) C17 0.067(4) 0.085(5) 0.069(4) 0.018(4) 0.010(3) -0.003(3) C18 0.061(4) 0.067(4) 0.070(4) -0.001(3) 0.014(3) -0.011(3) C19 0.040(3) 0.046(3) 0.060(3) 0.000(2) 0.007(2) 0.004(3) C20 0.051(3) 0.052(3) 0.070(3) 0.004(3) 0.001(3) -0.005(3) C21 0.044(3) 0.067(4) 0.073(4) 0.011(3) -0.007(3) 0.004(3) C22 0.058(4) 0.076(4) 0.068(4) 0.002(3) -0.004(3) -0.003(3) C23 0.063(4) 0.063(4) 0.066(3) 0.000(3) 0.002(3) -0.009(3) C24 0.038(3) 0.056(4) 0.075(4) 0.001(3) 0.005(3) -0.002(3) # 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 S1 O1 1.427(4) . . ? S1 O2 1.434(4) . . ? S1 C19 1.769(5) . . ? S1 C1 1.818(6) . . ? Si1 O3 1.650(4) . . ? Si1 C9 1.863(6) . . ? Si1 C8 1.877(6) . . ? Si1 C4 1.890(6) . . ? O3 C3 1.428(6) . . ? O5 C14 1.321(7) . . ? O5 C15 1.486(6) . . ? O4 C14 1.340(6) . . ? O4 C13 1.444(7) . . ? O6 C14 1.200(6) . . ? C2 C13 1.517(7) . . ? C2 C3 1.524(7) . . ? C2 C1 1.542(7) . . ? C2 H2 1.0000 . . ? C10 C11 1.489(8) . . ? C10 C3 1.519(7) . . ? C10 H10A 0.9900 . . ? C10 H10B 0.9900 . . ? C3 H3 1.0000 . . ? C20 C21 1.373(8) . . ? C20 C19 1.386(8) . . ? C20 H20 0.9500 . . ? C19 C24 1.381(8) . . ? C13 H13A 0.9900 . . ? C13 H13B 0.9900 . . ? C16 C15 1.518(9) . . ? C16 H16A 0.9800 . . ? C16 H16B 0.9800 . . ? C16 H16C 0.9800 . . ? C23 C24 1.366(8) . . ? C23 C22 1.378(9) . . ? C23 H23 0.9500 . . ? C24 H24 0.9500 . . ? C4 C7 1.523(8) . . ? C4 C6 1.527(8) . . ? C4 C5 1.535(8) . . ? C11 C12 1.317(7) . . ? C11 H11 0.9500 . . ? C12 C1 1.498(7) . . ? C12 H12 0.9500 . . ? C15 C17 1.505(9) . . ? C15 C18 1.510(8) . . ? C22 C21 1.390(9) . . ? C22 H22 0.9500 . . ? C21 H21 0.9500 . . ? C1 H1 1.0000 . . ? C5 H5A 0.9800 . . ? C5 H5B 0.9800 . . ? C5 H5C 0.9800 . . ? C17 H17A 0.9800 . . ? C17 H17B 0.9800 . . ? C17 H17C 0.9800 . . ? C18 H18A 0.9800 . . ? C18 H18B 0.9800 . . ? C18 H18C 0.9800 . . ? C6 H6A 0.9800 . . ? C6 H6B 0.9800 . . ? C6 H6C 0.9800 . . ? C7 H7A 0.9800 . . ? C7 H7B 0.9800 . . ? C7 H7C 0.9800 . . ? C8 H8A 0.9800 . . ? C8 H8B 0.9800 . . ? C8 H8C 0.9800 . . ? C9 H9A 0.9800 . . ? C9 H9B 0.9800 . . ? C9 H9C 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.1(3) . . . ? O1 S1 C19 107.5(2) . . . ? O2 S1 C19 106.9(2) . . . ? O1 S1 C1 107.9(3) . . . ? O2 S1 C1 107.6(2) . . . ? C19 S1 C1 107.4(2) . . . ? O3 Si1 C9 109.7(2) . . . ? O3 Si1 C8 109.8(3) . . . ? C9 Si1 C8 108.7(3) . . . ? O3 Si1 C4 104.9(2) . . . ? C9 Si1 C4 111.7(3) . . . ? C8 Si1 C4 112.0(3) . . . ? C3 O3 Si1 123.5(3) . . . ? C14 O5 C15 119.9(4) . . . ? C14 O4 C13 114.5(4) . . . ? O6 C14 O5 127.5(5) . . . ? O6 C14 O4 125.0(5) . . . ? O5 C14 O4 107.5(4) . . . ? C13 C2 C3 113.7(4) . . . ? C13 C2 C1 114.4(4) . . . ? C3 C2 C1 109.5(4) . . . ? C13 C2 H2 106.20 . . . ? C3 C2 H2 106.20 . . . ? C1 C2 H2 106.20 . . . ? C11 C10 C3 111.5(4) . . . ? C11 C10 H10A 109.30 . . . ? C3 C10 H10A 109.30 . . . ? C11 C10 H10B 109.30 . . . ? C3 C10 H10B 109.30 . . . ? H10A C10 H10B 108.00 . . . ? O3 C3 C10 109.8(4) . . . ? O3 C3 C2 109.1(4) . . . ? C10 C3 C2 109.6(4) . . . ? O3 C3 H3 109.40 . . . ? C10 C3 H3 109.40 . . . ? C2 C3 H3 109.40 . . . ? C21 C20 C19 120.5(5) . . . ? C21 C20 H20 119.70 . . . ? C19 C20 H20 119.70 . . . ? C24 C19 C20 120.0(5) . . . ? C24 C19 S1 119.2(4) . . . ? C20 C19 S1 120.6(4) . . . ? O4 C13 C2 108.6(4) . . . ? O4 C13 H13A 110.00 . . . ? C2 C13 H13A 110.00 . . . ? O4 C13 H13B 110.00 . . . ? C2 C13 H13B 110.00 . . . ? H13A C13 H13B 108.30 . . . ? C15 C16 H16A 109.50 . . . ? C15 C16 H16B 109.50 . . . ? H16A C16 H16B 109.50 . . . ? C15 C16 H16C 109.50 . . . ? H16A C16 H16C 109.50 . . . ? H16B C16 H16C 109.50 . . . ? C24 C23 C22 120.3(6) . . . ? C24 C23 H23 119.80 . . . ? C22 C23 H23 119.80 . . . ? C23 C24 C19 119.8(6) . . . ? C23 C24 H24 120.10 . . . ? C19 C24 H24 120.10 . . . ? C7 C4 C6 109.6(6) . . . ? C7 C4 C5 109.9(5) . . . ? C6 C4 C5 109.7(5) . . . ? C7 C4 Si1 110.1(4) . . . ? C6 C4 Si1 109.2(4) . . . ? C5 C4 Si1 108.3(4) . . . ? C12 C11 C10 122.8(5) . . . ? C12 C11 H11 118.60 . . . ? C10 C11 H11 118.60 . . . ? C11 C12 C1 123.3(5) . . . ? C11 C12 H12 118.30 . . . ? C1 C12 H12 118.30 . . . ? O5 C15 C17 102.2(4) . . . ? O5 C15 C18 108.9(4) . . . ? C17 C15 C18 110.8(6) . . . ? O5 C15 C16 110.4(5) . . . ? C17 C15 C16 111.3(5) . . . ? C18 C15 C16 112.7(5) . . . ? C23 C22 C21 120.5(6) . . . ? C23 C22 H22 119.70 . . . ? C21 C22 H22 119.70 . . . ? C20 C21 C22 118.8(5) . . . ? C20 C21 H21 120.60 . . . ? C22 C21 H21 120.60 . . . ? C12 C1 C2 113.6(4) . . . ? C12 C1 S1 110.8(4) . . . ? C2 C1 S1 107.1(4) . . . ? C12 C1 H1 108.40 . . . ? C2 C1 H1 108.40 . . . ? S1 C1 H1 108.40 . . . ? C4 C5 H5A 109.50 . . . ? C4 C5 H5B 109.50 . . . ? H5A C5 H5B 109.50 . . . ? C4 C5 H5C 109.50 . . . ? H5A C5 H5C 109.50 . . . ? H5B C5 H5C 109.50 . . . ? C15 C17 H17A 109.50 . . . ? C15 C17 H17B 109.50 . . . ? H17A C17 H17B 109.50 . . . ? C15 C17 H17C 109.50 . . . ? H17A C17 H17C 109.50 . . . ? H17B C17 H17C 109.50 . . . ? C15 C18 H18A 109.50 . . . ? C15 C18 H18B 109.50 . . . ? H18A C18 H18B 109.50 . . . ? C15 C18 H18C 109.50 . . . ? H18A C18 H18C 109.50 . . . ? H18B C18 H18C 109.50 . . . ? C4 C6 H6A 109.50 . . . ? C4 C6 H6B 109.50 . . . ? H6A C6 H6B 109.50 . . . ? C4 C6 H6C 109.50 . . . ? H6A C6 H6C 109.50 . . . ? H6B C6 H6C 109.50 . . . ? C4 C7 H7A 109.50 . . . ? C4 C7 H7B 109.50 . . . ? H7A C7 H7B 109.50 . . . ? C4 C7 H7C 109.50 . . . ? H7A C7 H7C 109.50 . . . ? H7B C7 H7C 109.50 . . . ? Si1 C8 H8A 109.50 . . . ? Si1 C8 H8B 109.50 . . . ? H8A C8 H8B 109.50 . . . ? Si1 C8 H8C 109.50 . . . ? H8A C8 H8C 109.50 . . . ? H8B C8 H8C 109.50 . . . ? Si1 C9 H9A 109.50 . . . ? Si1 C9 H9B 109.50 . . . ? H9A C9 H9B 109.50 . . . ? Si1 C9 H9C 109.50 . . . ? H9A C9 H9C 109.50 . . . ? H9B C9 H9C 109.50 . . . ? 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 C9 Si1 O3 C3 63.3(4) . . . . ? C8 Si1 O3 C3 -56.1(4) . . . . ? C4 Si1 O3 C3 -176.6(4) . . . . ? C15 O5 C14 O6 3.2(8) . . . . ? C15 O5 C14 O4 -177.6(4) . . . . ? C13 O4 C14 O6 3.7(8) . . . . ? C13 O4 C14 O5 -175.5(4) . . . . ? Si1 O3 C3 C10 101.9(5) . . . . ? Si1 O3 C3 C2 -137.9(4) . . . . ? C11 C10 C3 O3 172.0(4) . . . . ? C11 C10 C3 C2 52.2(6) . . . . ? C13 C2 C3 O3 48.7(6) . . . . ? C1 C2 C3 O3 178.0(4) . . . . ? C13 C2 C3 C10 169.0(4) . . . . ? C1 C2 C3 C10 -61.7(5) . . . . ? C21 C20 C19 C24 -1.8(8) . . . . ? C21 C20 C19 S1 -176.4(5) . . . . ? O1 S1 C19 C24 -127.6(4) . . . . ? O2 S1 C19 C24 1.4(5) . . . . ? C1 S1 C19 C24 116.6(4) . . . . ? O1 S1 C19 C20 47.1(5) . . . . ? O2 S1 C19 C20 176.0(4) . . . . ? C1 S1 C19 C20 -68.8(5) . . . . ? C14 O4 C13 C2 -163.2(4) . . . . ? C3 C2 C13 O4 71.9(5) . . . . ? C1 C2 C13 O4 -54.8(6) . . . . ? C22 C23 C24 C19 -1.0(9) . . . . ? C20 C19 C24 C23 0.7(8) . . . . ? S1 C19 C24 C23 175.4(4) . . . . ? O3 Si1 C4 C7 -63.7(5) . . . . ? C9 Si1 C4 C7 55.1(5) . . . . ? C8 Si1 C4 C7 177.3(5) . . . . ? O3 Si1 C4 C6 56.7(4) . . . . ? C9 Si1 C4 C6 175.4(4) . . . . ? C8 Si1 C4 C6 -62.4(5) . . . . ? O3 Si1 C4 C5 176.1(4) . . . . ? C9 Si1 C4 C5 -65.1(4) . . . . ? C8 Si1 C4 C5 57.1(5) . . . . ? C3 C10 C11 C12 -20.2(7) . . . . ? C10 C11 C12 C1 -2.9(8) . . . . ? C14 O5 C15 C17 -178.6(5) . . . . ? C14 O5 C15 C18 64.1(6) . . . . ? C14 O5 C15 C16 -60.1(6) . . . . ? C24 C23 C22 C21 2.4(10) . . . . ? C19 C20 C21 C22 3.1(9) . . . . ? C23 C22 C21 C20 -3.4(9) . . . . ? C11 C12 C1 C2 -7.0(8) . . . . ? C11 C12 C1 S1 -127.6(5) . . . . ? C13 C2 C1 C12 167.7(5) . . . . ? C3 C2 C1 C12 38.8(6) . . . . ? C13 C2 C1 S1 -69.6(5) . . . . ? C3 C2 C1 S1 161.5(3) . . . . ? O1 S1 C1 C12 -157.2(4) . . . . ? O2 S1 C1 C12 73.2(4) . . . . ? C19 S1 C1 C12 -41.6(4) . . . . ? O1 S1 C1 C2 78.4(4) . . . . ? O2 S1 C1 C2 -51.3(4) . . . . ? C19 S1 C1 C2 -166.0(3) . . . . ? _iucr_refine_instruction_details ; TITL xl in P2(1) CELL 1.54178 12.3827 6.2563 16.7955 90.000 92.209 90.000 ZERR 2 0.0005 0.0003 0.0012 0.000 0.007 0.000 LATT -1 SYMM - X , 0.50000 + Y , - Z SFAC C H O SI S UNIT 48 76 12 2 2 OMIT 4 0 1 OMIT -1 1 1 OMIT 1 0 2 OMIT -1 0 3 OMIT 7 -2 5 OMIT 7 -3 15 OMIT 7 2 5 omit -2 120. TEMP -123.15 SIZE 0.02 0.12 0.20 L.S. 5 FMAP 2 PLAN -20 ACTA 120. BOND $H CONF WGHT 0.097400 1.372400 EXTI 0.000537 FVAR 0.91072 S1 5 0.712775 -0.160256 0.086579 11.00000 0.04360 0.05360 = 0.05802 0.00323 -0.00059 -0.00489 SI1 4 1.050277 0.468242 0.287176 11.00000 0.04324 0.05339 = 0.05637 0.00153 -0.00264 -0.00117 O3 3 1.007976 0.249042 0.241144 11.00000 0.04198 0.05773 = 0.05741 0.00628 -0.00154 0.00205 O5 3 0.621446 0.513727 0.296087 11.00000 0.04758 0.06272 = 0.05341 -0.00368 0.00225 0.01030 O1 3 0.623693 -0.144527 0.137713 11.00000 0.05248 0.07768 = 0.06719 -0.00245 0.00765 -0.02073 O4 3 0.725458 0.287642 0.241207 11.00000 0.04379 0.05997 = 0.05092 -0.00133 0.00335 0.00803 O2 3 0.789124 -0.330662 0.098749 11.00000 0.06093 0.05454 = 0.07336 0.00429 -0.01793 -0.00658 O6 3 0.707913 0.268051 0.374097 11.00000 0.06669 0.06975 = 0.05555 0.00766 0.01065 0.01208 C14 1 0.686717 0.350313 0.310837 11.00000 0.03836 0.06028 = 0.05429 -0.00236 -0.00104 -0.00879 C2 1 0.856558 0.084492 0.171077 11.00000 0.04149 0.04145 = 0.05332 -0.00233 0.00290 0.00317 AFIX 13 H2 2 0.892918 -0.058246 0.172724 11.00000 -1.20000 AFIX 0 C10 1 1.019270 0.196539 0.099377 11.00000 0.04255 0.04742 = 0.06974 0.00486 0.00600 -0.00144 AFIX 23 H10A 2 1.072067 0.313557 0.093032 11.00000 -1.20000 H10B 2 1.060089 0.064215 0.112393 11.00000 -1.20000 AFIX 0 C3 1 0.946520 0.250126 0.167409 11.00000 0.04096 0.04946 = 0.05229 0.00376 -0.00374 0.00362 AFIX 13 H3 2 0.914119 0.394946 0.158421 11.00000 -1.20000 AFIX 0 C20 1 0.577856 -0.049219 -0.040401 11.00000 0.05110 0.05219 = 0.06981 -0.00474 0.00051 0.00352 AFIX 43 H20 2 0.553294 0.062665 -0.007410 11.00000 -1.20000 AFIX 0 C19 1 0.659393 -0.184474 -0.012251 11.00000 0.04001 0.04630 = 0.06018 0.00421 0.00668 -0.00003 C13 1 0.792284 0.098663 0.246007 11.00000 0.03954 0.05648 = 0.05396 0.00065 -0.00309 0.00199 AFIX 23 H13A 2 0.746466 -0.030003 0.250867 11.00000 -1.20000 H13B 2 0.842008 0.106567 0.293505 11.00000 -1.20000 AFIX 0 C16 1 0.499086 0.468311 0.407363 11.00000 0.04926 0.08050 = 0.08580 -0.00240 0.02195 -0.00439 AFIX 137 H16A 2 0.453409 0.387575 0.369082 11.00000 -1.50000 H16B 2 0.453313 0.547752 0.443369 11.00000 -1.50000 H16C 2 0.545367 0.369244 0.438349 11.00000 -1.50000 AFIX 0 C23 1 0.647143 -0.380313 -0.133522 11.00000 0.06274 0.06251 = 0.06581 -0.00884 0.00239 0.00002 AFIX 43 H23 2 0.671244 -0.493423 -0.166137 11.00000 -1.20000 AFIX 0 C24 1 0.693341 -0.350952 -0.059137 11.00000 0.03818 0.05648 = 0.07468 -0.00206 0.00450 0.00068 AFIX 43 H24 2 0.748645 -0.444766 -0.039729 11.00000 -1.20000 AFIX 0 C4 1 1.133246 0.370394 0.376713 11.00000 0.04460 0.06561 = 0.05280 0.00012 -0.00222 -0.00115 C11 1 0.955805 0.166055 0.023099 11.00000 0.05086 0.04698 = 0.05590 -0.00060 0.00632 -0.00114 AFIX 43 H11 2 0.992016 0.178245 -0.025541 11.00000 -1.20000 AFIX 0 C12 1 0.851592 0.122908 0.020183 11.00000 0.04532 0.04759 = 0.05673 0.00100 0.00217 -0.00173 AFIX 43 H12 2 0.815470 0.112071 -0.030592 11.00000 -1.20000 AFIX 0 C15 1 0.569076 0.623818 0.362878 11.00000 0.04604 0.06489 = 0.06162 -0.00663 0.00993 0.00298 C22 1 0.565742 -0.246610 -0.161464 11.00000 0.05795 0.07576 = 0.06807 -0.00340 -0.00437 0.00241 AFIX 43 H22 2 0.532220 -0.271438 -0.212456 11.00000 -1.20000 AFIX 0 C21 1 0.532315 -0.075724 -0.115612 11.00000 0.04372 0.06667 = 0.07260 0.00419 -0.00742 0.01124 AFIX 43 H21 2 0.478922 0.021012 -0.135935 11.00000 -1.20000 AFIX 0 C1 1 0.787176 0.090073 0.092850 11.00000 0.04268 0.04448 = 0.05483 0.00086 -0.00118 0.00222 AFIX 13 H1 2 0.734031 0.209784 0.096193 11.00000 -1.20000 AFIX 0 C5 1 1.182602 0.565302 0.420089 11.00000 0.05110 0.07159 = 0.07027 -0.00310 -0.01009 0.00579 AFIX 137 H5A 2 1.217783 0.519500 0.470503 11.00000 -1.50000 H5B 2 1.125417 0.668443 0.430860 11.00000 -1.50000 H5C 2 1.236113 0.632383 0.386594 11.00000 -1.50000 AFIX 0 C17 1 0.501606 0.791049 0.320000 11.00000 0.06686 0.08455 = 0.06933 -0.00272 0.00979 0.01778 AFIX 137 H17A 2 0.548624 0.885371 0.290187 11.00000 -1.50000 H17B 2 0.462704 0.875324 0.358866 11.00000 -1.50000 H17C 2 0.449554 0.721349 0.283024 11.00000 -1.50000 AFIX 0 C18 1 0.655475 0.726280 0.416025 11.00000 0.06118 0.06747 = 0.07009 -0.01088 0.01390 -0.00136 AFIX 137 H18A 2 0.700258 0.614798 0.441621 11.00000 -1.50000 H18B 2 0.621454 0.812067 0.456954 11.00000 -1.50000 H18C 2 0.700803 0.818493 0.384003 11.00000 -1.50000 AFIX 0 C6 1 1.223258 0.224996 0.348650 11.00000 0.05630 0.07422 = 0.06720 -0.00914 -0.00709 0.00568 AFIX 137 H6A 2 1.267209 0.175589 0.394815 11.00000 -1.50000 H6B 2 1.268897 0.304556 0.312586 11.00000 -1.50000 H6C 2 1.191428 0.101546 0.320541 11.00000 -1.50000 AFIX 0 C7 1 1.061904 0.246884 0.432509 11.00000 0.06530 0.08311 = 0.06435 0.00664 0.00093 -0.00275 AFIX 137 H7A 2 1.026070 0.129588 0.403232 11.00000 -1.50000 H7B 2 1.007262 0.343015 0.453358 11.00000 -1.50000 H7C 2 1.106475 0.188576 0.476841 11.00000 -1.50000 AFIX 0 C8 1 1.132633 0.632950 0.218539 11.00000 0.07381 0.06758 = 0.06727 0.00044 0.00746 -0.01702 AFIX 137 H8A 2 1.197159 0.552671 0.204543 11.00000 -1.50000 H8B 2 1.154424 0.766322 0.245210 11.00000 -1.50000 H8C 2 1.089326 0.665874 0.170020 11.00000 -1.50000 AFIX 0 C9 1 0.932006 0.629355 0.317061 11.00000 0.05909 0.06036 = 0.07392 -0.00339 -0.01150 0.00431 AFIX 137 H9A 2 0.879468 0.639668 0.272074 11.00000 -1.50000 H9B 2 0.956183 0.773006 0.332716 11.00000 -1.50000 H9C 2 0.898139 0.560157 0.362118 11.00000 -1.50000 HKLF 4 REM xl in P2(1) REM R1 = 0.0677 for 3362 Fo > 4sig(Fo) and 0.0729 for all 3639 data REM 298 parameters refined using 1 restraints END WGHT 0.0971 1.3715 REM Highest difference peak 0.450, deepest hole -0.372, 1-sigma level 0.125 Q1 1 0.7100 -0.1547 0.1571 11.00000 0.05 0.45 Q2 1 0.6411 -0.2536 0.0823 11.00000 0.05 0.36 Q3 1 0.7067 0.2944 0.1839 11.00000 0.05 0.34 Q4 1 0.6643 -0.0279 0.1533 11.00000 0.05 0.32 Q5 1 0.6918 -0.1667 0.0333 11.00000 0.05 0.32 Q6 1 0.6351 -0.1552 0.1976 11.00000 0.05 0.32 Q7 1 0.7535 0.3629 0.2751 11.00000 0.05 0.31 Q8 1 1.0176 0.2355 0.0385 11.00000 0.05 0.31 Q9 1 0.7623 -0.2016 0.2620 11.00000 0.05 0.30 Q10 1 1.1341 0.6735 0.1594 11.00000 0.05 0.30 Q11 1 0.6181 -0.1682 0.0653 11.00000 0.05 0.30 Q12 1 0.7265 -0.0376 0.2266 11.00000 0.05 0.30 Q13 1 1.1863 0.5934 0.1914 11.00000 0.05 0.27 Q14 1 0.9800 0.2122 -0.0539 11.00000 0.05 0.27 Q15 1 0.3958 -0.0381 -0.1319 11.00000 0.05 0.27 Q16 1 1.0030 0.2848 0.4593 11.00000 0.05 0.27 Q17 1 0.9952 0.1738 0.4380 11.00000 0.05 0.26 Q18 1 0.9581 -0.0426 0.4370 11.00000 0.05 0.26 Q19 1 1.2013 0.6381 0.2107 11.00000 0.05 0.26 Q20 1 0.4630 0.2857 0.4819 11.00000 0.05 0.26 ;