data_global #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# ##CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-07-21 at 09:22:42 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx2\files\cifdoc.dat # CIF files read : bs34c dreduc struct #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2005-07-21 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ SUBMISSION DETAILS --------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Max Malacria' _publ_contact_author_address ; 'Institut de Chimie Moleculaire (FR2769), Laboratoire de Chimie Organique (UMR7611), Universite Pierre et Marie Curie, 4, Place Jussieu, 75005 Paris, France' ; _publ_contact_author_email max.malacria@upmc.fr _publ_contact_author_fax '33 1 44 27 73 60' _publ_contact_author_phone '33 1 44 27 35 86' _publ_requested_journal 'Organic Letters' _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Acta Crystallographica C. ; _publ_requested_category ? #------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------# _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #------------------ TITLE AND AUTHOR LIST------------------------------------# _publ_section_title ; 'A stereoselective route towards polyhydroxylated piperidines. A total synthesis of deoxymannojirimycin' ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address 'C. Boglio' ; 'Institut de Chimie Moleculaire (FR2769), Laboratoire de Chimie Organique' (UMR7611), Universite Pierre et Marie Curie,' 4, Place Jussieu, 75005 Paris, France' ; 'S. Stahlke' ; 'Institut de Chimie Moleculaire (FR2769), Laboratoire de Chimie Organique' (UMR7611), Universite Pierre et Marie Curie,' 4, Place Jussieu, 75005 Paris, France' ; 'S. Thorimbert' ; 'Institut de Chimie Moleculaire (FR2769), Laboratoire de Chimie Organique' (UMR7611), Universite Pierre et Marie Curie,' 4, Place Jussieu, 75005 Paris, France' ; 'M. Malacria' ; 'Institut de Chimie Moleculaire (FR2769), Laboratoire de Chimie Organique' (UMR7611), Universite Pierre et Marie Curie,' 4, Place Jussieu, 75005 Paris, France' ; #------------------ TEXT ----------------------------------------------------# _publ_section_synopsis ; # Insert blank lines between paragraphs ? ; _publ_section_abstract ; # Insert blank lines between paragraphs ? ; _publ_section_comment ; # Insert blank lines between paragraphs ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H., Kennard, O. & Taylor, R. (1983). Acc. Chem. Res. 16, 146-153. Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350. Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Beurskens, P.T., Beurskens, G., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft, The Netherlands. Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4 Diffractometer Data. University of Marburg, Germany. Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA. Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst, A24, 351-359 Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G., & Taylor, R. (1992). International Tables for Crystallography, Volume C. Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3, edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189. Oxford University Press. Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Spek, A.L. (1990). Acta Cryst. A46, C34 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; Figure 1. View of (I) (50% probability displacement ellipsoids) ; _publ_section_acknowledgements ; ? ; _publ_section_table_legends ; Table 1. Fractional atomic coordinates and equivalent isotropic displacement parameters (\%A^2^) Table 2. Selected geometric parameters (\%A ,\% ) ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_bs34c _audit_creation_date 2005-07-21T09:22:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C23 H37 N O8 S Si' _chemical_formula_sum 'C23 H37 N O8 S Si' _chemical_formula_weight 515.69 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5810(17) _cell_length_b 14.2050(10) _cell_length_c 14.3610(18) _cell_angle_alpha 90 _cell_angle_beta 98.096(11) _cell_angle_gamma 90 _cell_volume 2742.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 180 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 21.2 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type none #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 50118 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_full 30 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 7978 _reflns_number_gt 4766 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0643P)^2^+0.7617P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_number_reflns 7978 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1447 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.461 _refine_diff_density_min -0.312 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' S S 0.1246 0.1234 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Si1 Si 0.07100(4) 0.30986(4) 0.15017(4) 0.03420(15) Uani 1 d . . . S1 S 0.39486(4) 0.37551(3) 0.30816(3) 0.03337(14) Uani 1 d . . . N1 N 0.40073(12) 0.38307(10) 0.19500(10) 0.0286(3) Uani 1 d . . . O1 O 0.49452(11) 0.22952(9) 0.10285(10) 0.0382(3) Uani 1 d . . . O2 O 0.60215(14) 0.34260(12) 0.07923(14) 0.0639(5) Uani 1 d . . . O3 O 0.18351(10) 0.35658(9) 0.15722(9) 0.0351(3) Uani 1 d . . . O4 O 0.30481(10) 0.45500(9) -0.03193(9) 0.0347(3) Uani 1 d . . . O5 O 0.16238(14) 0.44185(16) -0.12905(12) 0.0724(6) Uani 1 d . . . O6 O 0.31303(14) 0.61215(9) 0.08796(12) 0.0506(4) Uani 1 d . . . H6 H 0.3343 0.6108 0.0373 0.076 Uiso 1 calc R . . O7 O 0.33538(11) 0.45000(11) 0.33854(10) 0.0460(4) Uani 1 d . . . O8 O 0.37043(12) 0.27963(10) 0.32660(10) 0.0465(4) Uani 1 d . . . C2 C 0.34685(14) 0.31486(12) 0.12890(12) 0.0286(4) Uani 1 d . . . H2 H 0.3341 0.259 0.1655 0.034 Uiso 1 calc R . . C3 C 0.24529(14) 0.35397(13) 0.08531(12) 0.0297(4) Uani 1 d . . . H3 H 0.2157 0.3124 0.0344 0.036 Uiso 1 calc R . . C4 C 0.25021(15) 0.45440(13) 0.04826(13) 0.0322(4) Uani 1 d . . . H4 H 0.1827 0.4784 0.0292 0.039 Uiso 1 calc R . . C5 C 0.30574(16) 0.51900(13) 0.12185(14) 0.0344(4) Uani 1 d . . . H5 H 0.268 0.5215 0.1752 0.041 Uiso 1 calc R . . C6 C 0.40788(15) 0.47926(13) 0.15754(13) 0.0325(4) Uani 1 d . . . H6A H 0.4477 0.4781 0.1066 0.039 Uiso 1 calc R . . H6B H 0.4409 0.5198 0.2067 0.039 Uiso 1 calc R . . C7 C 0.41201(16) 0.28381(14) 0.05655(13) 0.0362(5) Uani 1 d . . . H7A H 0.3734 0.246 0.0084 0.043 Uiso 1 calc R . . H7B H 0.4366 0.3385 0.0266 0.043 Uiso 1 calc R . . C8 C 0.58559(17) 0.26673(15) 0.10948(15) 0.0417(5) Uani 1 d . . . C9 C 0.66215(18) 0.20229(18) 0.15902(19) 0.0558(6) Uani 1 d . . . H9A H 0.6307 0.1458 0.1766 0.084 Uiso 1 calc R . . H9B H 0.6953 0.2328 0.2144 0.084 Uiso 1 calc R . . H9C H 0.7098 0.1868 0.118 0.084 Uiso 1 calc R . . C10 C 0.0814(2) 0.18062(16) 0.13625(19) 0.0584(7) Uani 1 d . . . H10A H 0.1235 0.1551 0.1896 0.088 Uiso 1 calc R . . H10B H 0.1095 0.1672 0.08 0.088 Uiso 1 calc R . . H10C H 0.0166 0.1527 0.132 0.088 Uiso 1 calc R . . C11 C -0.01045(19) 0.36046(18) 0.04743(18) 0.0555(6) Uani 1 d . . . H11A H -0.0155 0.4273 0.0553 0.083 Uiso 1 calc R . . H11B H -0.0754 0.3328 0.043 0.083 Uiso 1 calc R . . H11C H 0.0175 0.3474 -0.009 0.083 Uiso 1 calc R . . C12 C 0.02882(17) 0.34280(18) 0.26466(17) 0.0499(6) Uani 1 d . . . C13 C -0.0788(2) 0.3105(3) 0.2642(3) 0.1002(13) Uani 1 d . . . H13A H -0.1204 0.3391 0.2123 0.15 Uiso 1 calc R . . H13B H -0.1012 0.3289 0.322 0.15 Uiso 1 calc R . . H13C H -0.0823 0.2433 0.258 0.15 Uiso 1 calc R . . C14 C 0.0344(2) 0.4502(2) 0.2774(2) 0.0743(9) Uani 1 d . . . H14A H 0.1018 0.4708 0.278 0.111 Uiso 1 calc R . . H14B H 0.0123 0.4669 0.3359 0.111 Uiso 1 calc R . . H14C H -0.0075 0.4801 0.2264 0.111 Uiso 1 calc R . . C15 C 0.0970(2) 0.2979(2) 0.34723(18) 0.0704(8) Uani 1 d . . . H15A H 0.1641 0.319 0.3466 0.106 Uiso 1 calc R . . H15B H 0.0944 0.2306 0.3413 0.106 Uiso 1 calc R . . H15C H 0.0752 0.3161 0.4054 0.106 Uiso 1 calc R . . C16 C 0.25075(17) 0.45094(15) -0.11811(14) 0.0405(5) Uani 1 d . . . C17 C 0.31476(19) 0.45518(18) -0.19369(15) 0.0524(6) Uani 1 d . . . H17A H 0.3604 0.4032 -0.1871 0.079 Uiso 1 calc R . . H17B H 0.3513 0.5132 -0.1889 0.079 Uiso 1 calc R . . H17C H 0.274 0.4519 -0.2539 0.079 Uiso 1 calc R . . C18 C 0.51857(15) 0.39701(13) 0.35967(12) 0.0315(4) Uani 1 d . . . C19 C 0.54689(16) 0.48565(14) 0.39415(13) 0.0366(5) Uani 1 d . . . H19 H 0.5012 0.5348 0.3893 0.044 Uiso 1 calc R . . C20 C 0.64403(17) 0.50003(14) 0.43580(14) 0.0388(5) Uani 1 d . . . H20 H 0.6631 0.5594 0.459 0.047 Uiso 1 calc R . . C21 C 0.71341(16) 0.42813(15) 0.44379(14) 0.0384(5) Uani 1 d . . . C23 C 0.58726(16) 0.32423(14) 0.36673(15) 0.0393(5) Uani 1 d . . . H23 H 0.5685 0.2648 0.3434 0.047 Uiso 1 calc R . . C22 C 0.68313(17) 0.34028(15) 0.40835(16) 0.0428(5) Uani 1 d . . . H22 H 0.7288 0.2912 0.4129 0.051 Uiso 1 calc R . . C24 C 0.81745(18) 0.44504(19) 0.49193(19) 0.0590(7) Uani 1 d . . . H24A H 0.8555 0.3881 0.4913 0.089 Uiso 1 calc R . . H24B H 0.8154 0.464 0.5558 0.089 Uiso 1 calc R . . H24C H 0.8479 0.4938 0.4595 0.089 Uiso 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0349(3) 0.0366(3) 0.0310(3) 0.0011(2) 0.0044(2) -0.0049(2) S1 0.0403(3) 0.0408(3) 0.0188(2) 0.00075(18) 0.00334(18) -0.0047(2) N1 0.0377(9) 0.0283(8) 0.0192(7) 0.0005(6) 0.0018(6) -0.0076(7) O1 0.0430(9) 0.0286(7) 0.0437(8) 0.0037(6) 0.0085(7) 0.0011(6) O2 0.0692(12) 0.0465(10) 0.0799(13) 0.0106(9) 0.0245(10) -0.0168(9) O3 0.0365(8) 0.0429(8) 0.0270(7) -0.0007(6) 0.0083(6) -0.0104(6) O4 0.0361(8) 0.0445(8) 0.0225(6) 0.0075(5) 0.0008(6) -0.0058(6) O5 0.0501(12) 0.1226(17) 0.0404(10) -0.0038(10) -0.0074(8) -0.0010(11) O6 0.0752(12) 0.0241(7) 0.0529(10) 0.0076(6) 0.0109(9) -0.0028(7) O7 0.0427(9) 0.0660(10) 0.0301(7) -0.0115(7) 0.0080(6) 0.0055(7) O8 0.0602(10) 0.0489(9) 0.0290(7) 0.0120(6) 0.0014(7) -0.0180(8) C2 0.0397(11) 0.0250(9) 0.0208(8) -0.0007(7) 0.0034(8) -0.0055(8) C3 0.0366(11) 0.0322(10) 0.0205(8) 0.0002(7) 0.0045(7) -0.0084(8) C4 0.0356(11) 0.0349(10) 0.0257(9) 0.0060(7) 0.0033(8) -0.0014(8) C5 0.0467(12) 0.0257(9) 0.0310(10) 0.0039(7) 0.0060(9) -0.0035(9) C6 0.0439(12) 0.0292(10) 0.0241(9) -0.0001(7) 0.0032(8) -0.0116(9) C7 0.0469(13) 0.0352(10) 0.0266(10) -0.0025(8) 0.0051(9) 0.0011(9) C8 0.0486(14) 0.0385(12) 0.0405(12) -0.0066(9) 0.0150(10) -0.0073(10) C9 0.0441(14) 0.0620(16) 0.0615(16) -0.0062(12) 0.0079(12) 0.0042(12) C10 0.0755(19) 0.0416(13) 0.0562(16) -0.0007(11) 0.0023(13) -0.0137(12) C11 0.0487(14) 0.0695(16) 0.0456(14) -0.0006(12) -0.0032(11) 0.0068(12) C12 0.0435(14) 0.0659(15) 0.0420(13) -0.0048(11) 0.0120(10) -0.0034(12) C13 0.062(2) 0.167(4) 0.081(2) -0.032(2) 0.0407(18) -0.036(2) C14 0.085(2) 0.0764(19) 0.0594(17) -0.0241(14) 0.0046(15) 0.0191(16) C15 0.088(2) 0.091(2) 0.0345(13) 0.0112(13) 0.0173(13) 0.0014(17) C16 0.0465(14) 0.0451(12) 0.0275(10) 0.0054(8) -0.0032(9) -0.0027(10) C17 0.0714(17) 0.0594(15) 0.0268(10) 0.0050(10) 0.0080(11) -0.0127(12) C18 0.0412(11) 0.0331(10) 0.0194(8) 0.0000(7) 0.0016(8) 0.0000(8) C19 0.0482(13) 0.0327(10) 0.0280(10) -0.0035(8) 0.0021(9) 0.0051(9) C20 0.0531(13) 0.0351(11) 0.0274(10) -0.0057(8) 0.0027(9) -0.0067(10) C21 0.0425(12) 0.0455(12) 0.0268(10) 0.0013(8) 0.0030(8) -0.0039(10) C23 0.0502(13) 0.0306(10) 0.0355(11) -0.0035(8) 0.0000(9) -0.0016(9) C22 0.0464(13) 0.0373(11) 0.0434(12) 0.0009(9) 0.0012(10) 0.0082(10) C24 0.0470(15) 0.0707(17) 0.0567(15) -0.0038(13) -0.0020(12) -0.0062(13) #------------------ 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_2 _geom_bond_publ_flag Si1 O3 1.6559(14) . ? Si1 C10 1.854(2) . ? Si1 C11 1.859(2) . ? Si1 C12 1.875(2) . ? S1 O8 1.4353(15) . ? S1 O7 1.4358(15) . ? S1 N1 1.6417(15) . ? S1 C18 1.764(2) . ? N1 C6 1.477(2) . ? N1 C2 1.476(2) . ? O1 C8 1.336(3) . ? O1 C7 1.443(2) . ? O2 C8 1.195(3) . ? O3 C3 1.420(2) . ? O4 C16 1.348(2) . ? O4 C4 1.455(2) . ? O5 C16 1.195(3) . ? O6 C5 1.418(2) . ? O6 H6 0.82 . ? C2 C7 1.522(3) . ? C2 C3 1.536(3) . ? C2 H2 0.98 . ? C3 C4 1.527(3) . ? C3 H3 0.98 . ? C4 C5 1.518(3) . ? C4 H4 0.98 . ? C5 C6 1.518(3) . ? C5 H5 0.98 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.489(3) . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 C13 1.531(4) . ? C12 C15 1.537(4) . ? C12 C14 1.538(4) . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 C17 1.484(3) . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? C18 C23 1.387(3) . ? C18 C19 1.387(3) . ? C19 C20 1.385(3) . ? C19 H19 0.93 . ? C20 C21 1.383(3) . ? C20 H20 0.93 . ? C21 C22 1.388(3) . ? C21 C24 1.502(3) . ? C23 C22 1.373(3) . ? C23 H23 0.93 . ? C22 H22 0.93 . ? C24 H24A 0.96 . ? C24 H24B 0.96 . ? C24 H24C 0.96 . ? 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 C10 108.65(10) . . ? O3 Si1 C11 109.53(10) . . ? C10 Si1 C11 110.06(12) . . ? O3 Si1 C12 103.86(9) . . ? C10 Si1 C12 112.27(12) . . ? C11 Si1 C12 112.23(12) . . ? O8 S1 O7 119.25(10) . . ? O8 S1 N1 106.83(8) . . ? O7 S1 N1 111.12(9) . . ? O8 S1 C18 108.54(9) . . ? O7 S1 C18 106.76(9) . . ? N1 S1 C18 103.16(8) . . ? C6 N1 C2 115.16(14) . . ? C6 N1 S1 115.85(12) . . ? C2 N1 S1 120.31(12) . . ? C8 O1 C7 118.19(16) . . ? C3 O3 Si1 125.44(12) . . ? C16 O4 C4 116.99(16) . . ? C5 O6 H6 109.5 . . ? N1 C2 C7 110.24(16) . . ? N1 C2 C3 111.10(15) . . ? C7 C2 C3 113.68(15) . . ? N1 C2 H2 107.2 . . ? C7 C2 H2 107.2 . . ? C3 C2 H2 107.2 . . ? O3 C3 C4 106.76(15) . . ? O3 C3 C2 107.56(14) . . ? C4 C3 C2 113.51(15) . . ? O3 C3 H3 109.6 . . ? C4 C3 H3 109.6 . . ? C2 C3 H3 109.6 . . ? O4 C4 C5 106.80(15) . . ? O4 C4 C3 109.47(15) . . ? C5 C4 C3 111.35(15) . . ? O4 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? O6 C5 C6 110.99(16) . . ? O6 C5 C4 112.16(16) . . ? C6 C5 C4 110.55(16) . . ? O6 C5 H5 107.6 . . ? C6 C5 H5 107.6 . . ? C4 C5 H5 107.6 . . ? N1 C6 C5 111.30(15) . . ? N1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108 . . ? O1 C7 C2 109.19(15) . . ? O1 C7 H7A 109.8 . . ? C2 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? C2 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O2 C8 O1 123.4(2) . . ? O2 C8 C9 125.0(2) . . ? O1 C8 C9 111.60(19) . . ? 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 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 . . ? 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 . . ? C13 C12 C15 110.5(3) . . ? C13 C12 C14 109.2(3) . . ? C15 C12 C14 107.8(2) . . ? C13 C12 Si1 109.31(18) . . ? C15 C12 Si1 110.35(17) . . ? C14 C12 Si1 109.65(18) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O4 122.2(2) . . ? O5 C16 C17 126.1(2) . . ? O4 C16 C17 111.72(19) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 120.05(19) . . ? C23 C18 S1 119.52(15) . . ? C19 C18 S1 120.42(15) . . ? C20 C19 C18 119.17(19) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 121.55(19) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C20 C21 C22 118.0(2) . . ? C20 C21 C24 120.4(2) . . ? C22 C21 C24 121.6(2) . . ? C22 C23 C18 119.67(19) . . ? C22 C23 H23 120.2 . . ? C18 C23 H23 120.2 . . ? C23 C22 C21 121.5(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ?