# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'CRICH, David' _publ_contact_author_address ;Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; _publ_contact_author_email david.crich@icsn.cnrs-gif.fr _publ_contact_author_phone +33169823089 _publ_contact_author_fax +33169077247 loop_ _publ_author_name _publ_author_address S.AUBRY ;Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; P.RETAILLEAU ;Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; D.CRICH ;Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; _audit_creation_date 23-12-10 _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Sheldrick, G.M. (2008).Acta Cryst. A64, 112-122. Spek, A. L. (2003). J.Appl. Cryst. 36, 7-13. Welter, R. (2006). The Crystalbuilder Project Acta Cryst. A62, s252. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_sa217 _database_code_depnum_ccdc_archive 'CCDC 805687' #TrackingRef 'web_deposit_cif_file_0_PascalRetailleau_1293116303.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-tert-butyl (2-oxothietan-3-yl)carbamate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H13 N O3 S' _chemical_formula_sum 'C8 H13 N O3 S' _chemical_formula_weight 203.25 _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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1207(4) _cell_length_b 18.0019(11) _cell_length_c 5.8831(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.066(8) _cell_angle_gamma 90.00 _cell_volume 512.57(7) _cell_formula_units_Z 2 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 1563 _cell_measurement_theta_min 7.4 _cell_measurement_theta_max 71.9 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 2.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_type 'RAPID II large area curved imaging plate detector ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3523 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 7.97 _diffrn_reflns_theta_max 68.24 _reflns_number_total 1510 _reflns_number_gt 1295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0550P)^2^+0.9664P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881;552 Friedel pairs' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 1510 _refine_ls_number_parameters 121 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.6825(4) 0.57877(9) -0.0337(3) 0.0590(5) Uani 1 1 d . . . O3 O 0.8629(9) 0.7574(3) 0.2521(8) 0.0476(11) Uani 1 1 d . . . O4 O 0.6167(8) 0.8394(2) 0.3983(8) 0.0444(11) Uani 1 1 d . . . O2 O 0.7608(12) 0.5982(3) 0.4439(9) 0.0676(15) Uani 1 1 d . . . N1 N 0.4140(10) 0.7380(3) 0.2164(9) 0.0438(13) Uani 1 1 d . . . H1N H 0.2635 0.7619 0.2602 0.053 Uiso 1 1 d R . . C5 C 0.6489(11) 0.7780(3) 0.2907(11) 0.0392(14) Uani 1 1 d . . . C6 C 0.8511(13) 0.8919(4) 0.5025(10) 0.0428(15) Uani 1 1 d . . . C3 C 0.4162(14) 0.6658(4) 0.1108(12) 0.0493(17) Uani 1 1 d . . . H3 H 0.2374 0.6412 0.0998 0.059 Uiso 1 1 calc R . . C2 C 0.6453(15) 0.6120(4) 0.2391(12) 0.0502(16) Uani 1 1 d . . . C9 C 1.0777(15) 0.8521(5) 0.6991(12) 0.0555(19) Uani 1 1 d . . . H9A H 0.9975 0.8281 0.8104 0.083 Uiso 1 1 calc R . . H9B H 1.2175 0.8882 0.7871 0.083 Uiso 1 1 calc R . . H9C H 1.1640 0.8145 0.6264 0.083 Uiso 1 1 calc R . . C4 C 0.4515(16) 0.6587(5) -0.1363(11) 0.059(2) Uani 1 1 d . . . H4A H 0.5427 0.7022 -0.1809 0.071 Uiso 1 1 calc R . . H4B H 0.2779 0.6464 -0.2664 0.071 Uiso 1 1 calc R . . C7 C 0.9438(15) 0.9244(4) 0.3057(11) 0.0488(17) Uani 1 1 d . . . H7A H 1.0446 0.8866 0.2476 0.073 Uiso 1 1 calc R . . H7B H 1.0650 0.9670 0.3686 0.073 Uiso 1 1 calc R . . H7C H 0.7821 0.9407 0.1727 0.073 Uiso 1 1 calc R . . C8 C 0.7177(16) 0.9520(4) 0.6076(13) 0.0562(19) Uani 1 1 d . . . H8A H 0.5695 0.9758 0.4783 0.084 Uiso 1 1 calc R . . H8B H 0.8567 0.9892 0.6883 0.084 Uiso 1 1 calc R . . H8C H 0.6406 0.9299 0.7241 0.084 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0571(10) 0.0487(11) 0.0649(10) -0.0180(9) 0.0112(8) 0.0039(10) O3 0.035(2) 0.038(3) 0.069(3) -0.007(2) 0.0161(19) 0.003(2) O4 0.035(2) 0.037(3) 0.061(3) -0.012(2) 0.0156(18) 0.000(2) O2 0.082(4) 0.055(4) 0.065(3) 0.012(3) 0.023(3) 0.012(3) N1 0.036(3) 0.037(3) 0.058(3) -0.011(2) 0.013(2) 0.002(2) C5 0.030(3) 0.033(4) 0.051(3) 0.000(3) 0.009(2) 0.005(3) C6 0.044(4) 0.034(4) 0.042(3) -0.005(3) 0.004(3) -0.005(3) C3 0.045(4) 0.038(4) 0.060(4) -0.008(3) 0.010(3) -0.009(3) C2 0.063(4) 0.032(4) 0.054(4) -0.004(3) 0.017(3) -0.001(3) C9 0.051(4) 0.060(5) 0.048(4) 0.004(3) 0.007(3) 0.005(4) C4 0.064(4) 0.058(5) 0.045(4) -0.011(3) 0.003(3) 0.018(4) C7 0.059(4) 0.040(4) 0.049(4) 0.002(3) 0.020(3) -0.003(3) C8 0.063(4) 0.044(4) 0.060(4) -0.016(3) 0.019(3) -0.003(4) _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 C2 1.780(7) . ? S1 C4 1.835(7) . ? O3 C5 1.246(7) . ? O4 C5 1.311(7) . ? O4 C6 1.493(7) . ? O2 C2 1.183(8) . ? N1 C5 1.346(8) . ? N1 C3 1.443(8) . ? N1 H1N 0.9872 . ? C6 C7 1.506(9) . ? C6 C8 1.515(9) . ? C6 C9 1.523(9) . ? C3 C2 1.519(10) . ? C3 C4 1.528(9) . ? C3 H3 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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_3 _geom_angle_publ_flag C2 S1 C4 77.7(3) . . ? C5 O4 C6 121.4(5) . . ? C5 N1 C3 119.3(5) . . ? C5 N1 H1N 112.0 . . ? C3 N1 H1N 128.4 . . ? O3 C5 O4 126.6(5) . . ? O3 C5 N1 121.9(6) . . ? O4 C5 N1 111.6(5) . . ? O4 C6 C7 110.1(5) . . ? O4 C6 C8 102.1(5) . . ? C7 C6 C8 109.5(6) . . ? O4 C6 C9 109.0(5) . . ? C7 C6 C9 114.4(6) . . ? C8 C6 C9 111.0(5) . . ? N1 C3 C2 118.3(5) . . ? N1 C3 C4 120.3(6) . . ? C2 C3 C4 96.1(6) . . ? N1 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? O2 C2 C3 133.5(7) . . ? O2 C2 S1 133.1(6) . . ? C3 C2 S1 93.4(4) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C4 S1 90.9(4) . . ? C3 C4 H4A 113.5 . . ? S1 C4 H4A 113.5 . . ? C3 C4 H4B 113.5 . . ? S1 C4 H4B 113.5 . . ? H4A C4 H4B 110.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C6 O4 C5 O3 -3.4(10) . . . . ? C6 O4 C5 N1 178.2(5) . . . . ? C3 N1 C5 O3 6.4(9) . . . . ? C3 N1 C5 O4 -175.2(5) . . . . ? C5 O4 C6 C7 64.7(7) . . . . ? C5 O4 C6 C8 -179.1(6) . . . . ? C5 O4 C6 C9 -61.6(7) . . . . ? C5 N1 C3 C2 47.7(9) . . . . ? C5 N1 C3 C4 -69.4(8) . . . . ? N1 C3 C2 O2 37.8(12) . . . . ? C4 C3 C2 O2 167.2(9) . . . . ? N1 C3 C2 S1 -140.8(5) . . . . ? C4 C3 C2 S1 -11.4(5) . . . . ? C4 S1 C2 O2 -169.0(9) . . . . ? C4 S1 C2 C3 9.6(5) . . . . ? N1 C3 C4 S1 139.0(6) . . . . ? C2 C3 C4 S1 11.0(5) . . . . ? C2 S1 C4 C3 -9.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.305 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.086