# 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