# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cs310 _database_code_depnum_ccdc_archive 'CCDC 870052' #TrackingRef '9930_web_deposit_cif_file_0_TatsuyaUchida_1330906757.cs310.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H23 N O2 S Si' _chemical_formula_sum 'C17 H23 N O2 S Si' _chemical_formula_weight 333.51 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 '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+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.0186(10) _cell_length_b 11.5512(18) _cell_length_c 24.941(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1733.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 9935 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9617 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 19254 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3960 _reflns_number_gt 3676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.1534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.05(6) _refine_ls_number_reflns 3960 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0682 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 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 S1 S 0.62775(6) 0.15009(3) 0.112172(14) 0.01670(9) Uani 1 1 d . . . Si1 Si 0.60977(7) 0.42181(3) 0.238974(16) 0.01786(10) Uani 1 1 d . . . O2 O 0.7032(2) 0.21225(9) 0.06573(4) 0.0252(3) Uani 1 1 d . . . O1 O 0.78158(19) 0.07243(10) 0.13730(5) 0.0242(3) Uani 1 1 d . . . N1 N 0.3970(2) 0.07437(10) 0.10039(5) 0.0180(3) Uani 1 1 d . . . C11 C 0.8530(3) 0.50236(15) 0.26586(7) 0.0284(4) Uani 1 1 d . . . H11A H 0.8081 0.5468 0.2965 0.043 Uiso 1 1 calc R . . H11B H 0.9099 0.5533 0.2387 0.043 Uiso 1 1 calc R . . H11C H 0.9666 0.4485 0.2762 0.043 Uiso 1 1 calc R . . C17 C 0.4642(3) 0.34061(15) 0.29285(7) 0.0260(4) Uani 1 1 d . . . H17A H 0.3998 0.3943 0.3178 0.039 Uiso 1 1 calc R . . H17B H 0.5685 0.2918 0.3112 0.039 Uiso 1 1 calc R . . H17C H 0.3491 0.2938 0.2774 0.039 Uiso 1 1 calc R . . C10 C 0.4133(3) 0.52326(13) 0.20570(7) 0.0250(4) Uani 1 1 d . . . H10A H 0.2911 0.4804 0.1909 0.038 Uiso 1 1 calc R . . H10B H 0.4888 0.5638 0.1775 0.038 Uiso 1 1 calc R . . H10C H 0.3585 0.5779 0.2315 0.038 Uiso 1 1 calc R . . C2 C 0.3321(3) -0.54685(14) 0.05040(6) 0.0222(3) Uani 1 1 d . . . H2 H 0.4050 -0.6137 0.0393 0.027 Uiso 1 1 calc R . . C12 C 0.2798(3) 0.09366(13) 0.04900(6) 0.0224(3) Uani 1 1 d . . . H12A H 0.3385 0.1524 0.0251 0.027 Uiso 1 1 calc R . . H12B H 0.1193 0.0865 0.0489 0.027 Uiso 1 1 calc R . . C1 C 0.1204(3) -0.55472(13) 0.07416(6) 0.0222(3) Uani 1 1 d . . . H1 H 0.0525 -0.6266 0.0780 0.027 Uiso 1 1 calc R . . C13 C 0.0142(3) -0.45725(14) 0.09165(6) 0.0213(3) Uani 1 1 d . . . H13 H -0.1242 -0.4637 0.1080 0.026 Uiso 1 1 calc R . . C15 C 0.0078(3) -0.24303(14) 0.10266(6) 0.0204(3) Uani 1 1 d . . . H15 H -0.1286 -0.2471 0.1201 0.025 Uiso 1 1 calc R . . C9 C 0.7143(3) 0.31710(14) 0.18681(6) 0.0199(3) Uani 1 1 d . . . H9A H 0.7943 0.3596 0.1594 0.024 Uiso 1 1 calc R . . H9B H 0.8174 0.2635 0.2034 0.024 Uiso 1 1 calc R . . C16 C 0.1036(3) -0.13753(13) 0.09437(6) 0.0196(3) Uani 1 1 d . . . H16 H 0.0321 -0.0708 0.1061 0.023 Uiso 1 1 calc R . . C3 C 0.4309(3) -0.44159(13) 0.04355(6) 0.0186(3) Uani 1 1 d . . . H3 H 0.5706 -0.4375 0.0278 0.022 Uiso 1 1 calc R . . C7 C 0.4127(3) -0.01367(12) 0.05657(6) 0.0189(3) Uani 1 1 d . . . H7 H 0.5549 -0.0156 0.0374 0.023 Uiso 1 1 calc R . . C8 C 0.5262(3) 0.24881(13) 0.16064(6) 0.0186(3) Uani 1 1 d . . . H8A H 0.4237 0.3022 0.1436 0.022 Uiso 1 1 calc R . . H8B H 0.4454 0.2066 0.1880 0.022 Uiso 1 1 calc R . . C6 C 0.3122(3) -0.12901(13) 0.06796(6) 0.0170(3) Uani 1 1 d . . . C5 C 0.4188(2) -0.22714(13) 0.05180(6) 0.0172(3) Uani 1 1 d . . . H5 H 0.5563 -0.2212 0.0350 0.021 Uiso 1 1 calc R . . C14 C 0.1118(3) -0.34649(13) 0.08526(6) 0.0170(3) Uani 1 1 d . . . C4 C 0.3238(2) -0.33852(12) 0.06014(6) 0.0159(3) 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 S1 0.01667(17) 0.01506(16) 0.01837(18) -0.00269(14) 0.00107(15) 0.00093(15) Si1 0.0169(2) 0.0180(2) 0.0187(2) -0.00375(16) 0.00023(17) -0.00048(18) O2 0.0290(6) 0.0240(6) 0.0226(6) -0.0022(5) 0.0050(5) -0.0048(5) O1 0.0203(6) 0.0197(5) 0.0326(6) -0.0038(5) -0.0040(5) 0.0039(5) N1 0.0180(6) 0.0167(6) 0.0193(6) -0.0032(5) -0.0015(5) 0.0003(6) C11 0.0229(9) 0.0313(9) 0.0310(9) -0.0120(8) -0.0006(8) -0.0012(7) C17 0.0311(9) 0.0238(8) 0.0231(8) -0.0038(7) 0.0034(7) -0.0017(7) C10 0.0258(9) 0.0239(8) 0.0253(8) -0.0025(6) -0.0006(7) 0.0043(7) C2 0.0286(9) 0.0196(7) 0.0185(8) -0.0012(6) -0.0015(7) 0.0045(6) C12 0.0252(8) 0.0206(8) 0.0216(8) -0.0008(7) -0.0076(7) 0.0001(7) C1 0.0287(9) 0.0180(7) 0.0200(8) 0.0034(6) -0.0050(7) -0.0055(7) C13 0.0177(8) 0.0280(9) 0.0183(8) 0.0039(7) -0.0007(6) -0.0039(6) C15 0.0143(8) 0.0279(8) 0.0191(8) 0.0010(7) 0.0024(6) 0.0008(6) C9 0.0174(8) 0.0206(8) 0.0218(8) -0.0034(6) 0.0025(6) -0.0006(6) C16 0.0206(7) 0.0190(7) 0.0191(7) -0.0018(6) 0.0010(6) 0.0058(7) C3 0.0182(8) 0.0208(8) 0.0169(7) -0.0013(6) 0.0010(6) 0.0018(6) C7 0.0225(8) 0.0188(7) 0.0155(7) -0.0035(6) -0.0004(6) 0.0001(6) C8 0.0201(8) 0.0176(7) 0.0182(7) -0.0040(6) 0.0016(6) 0.0026(6) C6 0.0182(8) 0.0186(8) 0.0141(7) -0.0010(6) -0.0027(6) -0.0016(6) C5 0.0156(8) 0.0218(7) 0.0141(7) -0.0002(6) 0.0001(6) 0.0000(6) C14 0.0151(7) 0.0211(7) 0.0148(7) 0.0026(6) -0.0020(6) 0.0003(7) C4 0.0163(7) 0.0184(7) 0.0131(7) 0.0001(6) -0.0017(5) 0.0010(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 S1 O1 1.4334(12) . ? S1 O2 1.4366(12) . ? S1 N1 1.6675(13) . ? S1 C8 1.7707(15) . ? Si1 C17 1.8582(17) . ? Si1 C10 1.8603(17) . ? Si1 C11 1.8599(17) . ? Si1 C9 1.8844(16) . ? N1 C12 1.4797(19) . ? N1 C7 1.4958(18) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C2 C3 1.364(2) . ? C2 C1 1.408(2) . ? C2 H2 0.9300 . ? C12 C7 1.487(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C1 C13 1.366(2) . ? C1 H1 0.9300 . ? C13 C14 1.417(2) . ? C13 H13 0.9300 . ? C15 C16 1.364(2) . ? C15 C14 1.417(2) . ? C15 H15 0.9300 . ? C9 C8 1.526(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C16 C6 1.421(2) . ? C16 H16 0.9300 . ? C3 C4 1.416(2) . ? C3 H3 0.9300 . ? C7 C6 1.491(2) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C6 C5 1.363(2) . ? C5 C4 1.423(2) . ? C5 H5 0.9300 . ? C14 C4 1.425(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 O1 S1 O2 117.45(7) . . ? O1 S1 N1 106.67(7) . . ? O2 S1 N1 112.55(7) . . ? O1 S1 C8 109.12(7) . . ? O2 S1 C8 109.74(7) . . ? N1 S1 C8 99.83(7) . . ? C17 Si1 C10 109.93(8) . . ? C17 Si1 C11 111.28(8) . . ? C10 Si1 C11 110.26(8) . . ? C17 Si1 C9 109.43(8) . . ? C10 Si1 C9 107.97(8) . . ? C11 Si1 C9 107.90(8) . . ? C12 N1 C7 59.98(9) . . ? C12 N1 S1 118.07(10) . . ? C7 N1 S1 115.62(10) . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C2 C1 120.30(15) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? N1 C12 C7 60.54(9) . . ? N1 C12 H12A 117.7 . . ? C7 C12 H12A 117.7 . . ? N1 C12 H12B 117.7 . . ? C7 C12 H12B 117.7 . . ? H12A C12 H12B 114.8 . . ? C13 C1 C2 120.29(14) . . ? C13 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C13 C14 120.96(15) . . ? C1 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C16 C15 C14 121.35(14) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C8 C9 Si1 112.31(11) . . ? C8 C9 H9A 109.1 . . ? Si1 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? Si1 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C15 C16 C6 120.38(14) . . ? C15 C16 H16 119.8 . . ? C6 C16 H16 119.8 . . ? C2 C3 C4 120.97(14) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C12 C7 C6 123.42(14) . . ? C12 C7 N1 59.47(9) . . ? C6 C7 N1 116.28(12) . . ? C12 C7 H7 115.3 . . ? C6 C7 H7 115.3 . . ? N1 C7 H7 115.3 . . ? C9 C8 S1 111.66(11) . . ? C9 C8 H8A 109.3 . . ? S1 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? S1 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C5 C6 C16 119.69(14) . . ? C5 C6 C7 119.71(13) . . ? C16 C6 C7 120.58(13) . . ? C6 C5 C4 121.28(14) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C13 C14 C15 122.96(14) . . ? C13 C14 C4 118.63(14) . . ? C15 C14 C4 118.41(13) . . ? C3 C4 C5 122.31(14) . . ? C3 C4 C14 118.82(13) . . ? C5 C4 C14 118.86(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.351 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.043 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual = -1, Ralpha = 0.065 ; data_cd864 _database_code_depnum_ccdc_archive 'CCDC 870579' #TrackingRef '9996_web_deposit_cif_file_0_TatsuyaUchida_1331133132.cd864.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H23 N O2 S Si' _chemical_formula_sum 'C14 H23 N O2 S Si' _chemical_formula_weight 297.48 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P12(1)1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8858(17) _cell_length_b 5.9432(9) _cell_length_c 12.636(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.350(2) _cell_angle_gamma 90.00 _cell_volume 808.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 6778 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details ? _exptl_special_details ; SADABS Sheldrick 1996 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 8897 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3621 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.0333P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.04(6) _refine_ls_number_reflns 3621 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.036 _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 S1 S 0.43432(3) 0.41443(7) 0.31729(3) 0.02090(10) Uani 1 1 d . . . Si1 Si 0.27134(4) 0.60863(7) -0.01538(3) 0.01862(10) Uani 1 1 d . . . O1 O 0.39287(11) 0.4886(2) 0.41474(9) 0.0311(3) Uani 1 1 d . . . O2 O 0.42717(11) 0.1782(2) 0.29342(10) 0.0287(3) Uani 1 1 d . . . N1 N 0.57866(12) 0.4933(2) 0.30943(9) 0.0192(3) Uani 1 1 d . . . C9 C 1.12535(17) 0.0240(4) 0.31445(15) 0.0396(5) Uani 1 1 d . . . H9A H 1.1964 0.0837 0.3596 0.059 Uiso 1 1 calc R . . H9B H 1.1334 0.0515 0.2409 0.059 Uiso 1 1 calc R . . H9C H 1.1201 -0.1351 0.3262 0.059 Uiso 1 1 calc R . . C14 C 0.26738(17) 0.9201(3) -0.01019(13) 0.0315(4) Uani 1 1 d . . . H14A H 0.3489 0.9786 -0.0137 0.047 Uiso 1 1 calc R . . H14B H 0.2406 0.9672 0.0555 0.047 Uiso 1 1 calc R . . H14C H 0.2105 0.9759 -0.0696 0.047 Uiso 1 1 calc R . . C1 C 0.11270(15) 0.5001(3) -0.00483(15) 0.0291(4) Uani 1 1 d . . . H1A H 0.0836 0.5661 0.0563 0.044 Uiso 1 1 calc R . . H1B H 0.1157 0.3395 0.0031 0.044 Uiso 1 1 calc R . . H1C H 0.0572 0.5389 -0.0684 0.044 Uiso 1 1 calc R . . C11 C 0.63036(16) 0.6779(3) 0.38179(12) 0.0266(4) Uani 1 1 d . . . H11A H 0.6895 0.7792 0.3563 0.032 Uiso 1 1 calc R . . H11B H 0.5757 0.7479 0.4263 0.032 Uiso 1 1 calc R . . C7 C 0.96902(15) 0.3409(3) 0.29302(13) 0.0262(4) Uani 1 1 d . . . H7 H 1.0156 0.4086 0.2456 0.031 Uiso 1 1 calc R . . C10 C 0.32362(16) 0.5076(3) -0.14110(12) 0.0262(4) Uani 1 1 d . . . H10A H 0.2620 0.5441 -0.2009 0.039 Uiso 1 1 calc R . . H10B H 0.3352 0.3475 -0.1375 0.039 Uiso 1 1 calc R . . H10C H 0.4006 0.5791 -0.1497 0.039 Uiso 1 1 calc R . . C8 C 1.00895(15) 0.1373(3) 0.34067(12) 0.0259(4) Uani 1 1 d . . . C6 C 0.86119(14) 0.4451(3) 0.31471(12) 0.0242(3) Uani 1 1 d . . . H6 H 0.8360 0.5807 0.2818 0.029 Uiso 1 1 calc R . . C12 C 0.93945(14) 0.0420(3) 0.41281(12) 0.0232(3) Uani 1 1 d . . . H12 H 0.9652 -0.0928 0.4463 0.028 Uiso 1 1 calc R . . C2 C 0.38305(14) 0.5018(3) 0.10111(11) 0.0222(3) Uani 1 1 d . . . H2A H 0.3855 0.3389 0.0975 0.027 Uiso 1 1 calc R . . H2B H 0.4654 0.5572 0.0945 0.027 Uiso 1 1 calc R . . C3 C 0.35150(14) 0.5701(3) 0.21040(12) 0.0222(3) Uani 1 1 d . . . H3A H 0.2632 0.5492 0.2108 0.027 Uiso 1 1 calc R . . H3B H 0.3697 0.7287 0.2218 0.027 Uiso 1 1 calc R . . C4 C 0.67095(13) 0.4437(3) 0.40746(11) 0.0217(3) Uani 1 1 d . . . H4 H 0.6358 0.3747 0.4668 0.026 Uiso 1 1 calc R . . C13 C 0.83163(14) 0.1457(3) 0.43565(11) 0.0212(3) Uani 1 1 d . . . H13 H 0.7866 0.0801 0.4847 0.025 Uiso 1 1 calc R . . C5 C 0.79064(14) 0.3455(3) 0.38614(11) 0.0200(3) 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 S1 0.01757(19) 0.0267(2) 0.01871(16) 0.00304(16) 0.00350(13) 0.00212(17) Si1 0.0195(2) 0.0171(2) 0.01878(19) 0.00101(16) 0.00129(15) -0.00046(18) O1 0.0264(6) 0.0464(8) 0.0221(5) 0.0067(5) 0.0088(4) 0.0075(6) O2 0.0206(6) 0.0270(7) 0.0383(6) 0.0053(6) 0.0031(5) -0.0015(5) N1 0.0177(6) 0.0221(7) 0.0170(6) -0.0015(5) 0.0001(5) 0.0004(5) C9 0.0244(9) 0.0547(13) 0.0407(10) 0.0063(10) 0.0081(7) 0.0053(9) C14 0.0422(11) 0.0218(9) 0.0313(8) -0.0003(8) 0.0082(8) -0.0014(9) C1 0.0198(8) 0.0258(9) 0.0406(9) 0.0030(8) 0.0003(7) 0.0000(7) C11 0.0273(9) 0.0265(9) 0.0251(7) -0.0082(7) 0.0013(6) -0.0017(7) C7 0.0203(8) 0.0346(10) 0.0244(7) 0.0026(7) 0.0052(6) -0.0066(7) C10 0.0357(9) 0.0234(8) 0.0191(7) 0.0003(7) 0.0026(6) 0.0008(8) C8 0.0169(8) 0.0366(11) 0.0231(7) -0.0025(7) -0.0014(6) -0.0024(7) C6 0.0239(8) 0.0262(9) 0.0213(7) 0.0019(7) -0.0006(6) -0.0027(7) C12 0.0193(8) 0.0262(9) 0.0223(7) 0.0010(6) -0.0030(6) -0.0018(7) C2 0.0181(7) 0.0284(9) 0.0192(7) -0.0030(6) 0.0004(6) 0.0029(7) C3 0.0188(8) 0.0273(9) 0.0202(7) 0.0019(6) 0.0018(5) 0.0048(7) C4 0.0202(7) 0.0303(9) 0.0138(6) -0.0007(6) -0.0002(5) -0.0003(7) C13 0.0181(7) 0.0274(9) 0.0171(6) -0.0009(6) -0.0005(5) -0.0070(7) C5 0.0166(7) 0.0267(9) 0.0154(6) -0.0022(6) -0.0015(5) -0.0036(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 S1 O2 1.4358(13) . ? S1 O1 1.4405(11) . ? S1 N1 1.6564(13) . ? S1 C3 1.7717(16) . ? Si1 C14 1.853(2) . ? Si1 C10 1.8630(16) . ? Si1 C1 1.8663(17) . ? Si1 C2 1.8783(16) . ? N1 C11 1.486(2) . ? N1 C4 1.5063(18) . ? C9 C8 1.513(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C11 C4 1.482(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C7 C6 1.389(2) . ? C7 C8 1.393(3) . ? C7 H7 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C8 C12 1.387(2) . ? C6 C5 1.399(2) . ? C6 H6 0.9300 . ? C12 C13 1.393(2) . ? C12 H12 0.9300 . ? C2 C3 1.5254(19) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.488(2) . ? C4 H4 0.9800 . ? C13 C5 1.385(2) . ? C13 H13 0.9300 . ? 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 O2 S1 O1 117.68(8) . . ? O2 S1 N1 106.68(7) . . ? O1 S1 N1 112.47(7) . . ? O2 S1 C3 110.14(8) . . ? O1 S1 C3 107.70(7) . . ? N1 S1 C3 100.87(7) . . ? C14 Si1 C10 111.33(8) . . ? C14 Si1 C1 108.43(8) . . ? C10 Si1 C1 110.48(8) . . ? C14 Si1 C2 109.00(8) . . ? C10 Si1 C2 108.43(7) . . ? C1 Si1 C2 109.13(8) . . ? C11 N1 C4 59.37(11) . . ? C11 N1 S1 116.74(10) . . ? C4 N1 S1 114.87(10) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C1 H1A 109.5 . . ? Si1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Si1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C11 N1 61.01(10) . . ? C4 C11 H11A 117.7 . . ? N1 C11 H11A 117.7 . . ? C4 C11 H11B 117.7 . . ? N1 C11 H11B 117.7 . . ? H11A C11 H11B 114.8 . . ? C6 C7 C8 121.44(15) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C8 C7 118.24(15) . . ? C12 C8 C9 121.06(17) . . ? C7 C8 C9 120.70(15) . . ? C7 C6 C5 119.85(16) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C12 C13 120.78(16) . . ? C8 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C3 C2 Si1 114.48(11) . . ? C3 C2 H2A 108.6 . . ? Si1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? Si1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2 C3 S1 113.26(11) . . ? C2 C3 H3A 108.9 . . ? S1 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? S1 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C11 C4 C5 124.75(14) . . ? C11 C4 N1 59.62(10) . . ? C5 C4 N1 115.14(11) . . ? C11 C4 H4 115.1 . . ? C5 C4 H4 115.1 . . ? N1 C4 H4 115.1 . . ? C5 C13 C12 120.78(14) . . ? C5 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C5 C6 118.88(15) . . ? C13 C5 C4 119.19(13) . . ? C6 C5 C4 121.90(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.298 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.050 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual = -1, Ralpha = 0.044 ;