# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
K.Szabo
H.-J.Federsel
A.Ertan
M.Seenivasaperumal

_publ_contact_author_name        'Kalman Szabo'
_publ_contact_author_address     
;
Department of Organic Chemistry
Stockholm University
Arrhenius Laboratory
Stockholm
10691
SWEDEN
;

_publ_contact_author_email       KALMAN@ORGAN.SU.SE

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Factors Influencing the Selectivity in
Asymmetric Oxidation of Sulfides Attached to Nitrogen
Containing Heterocycles
;

#==============================================================================
data_MSPC806P
_database_code_depnum_ccdc_archive 'CCDC 634379'
#==============================================================================
_audit_creation_method           'maXus, shelxl and PLATON'
_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N2 O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C4 H6 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         130.18
_chemical_compound_source        'Local laboratory'

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_cell_measurement_temperature    293
_refine_ls_hydrogen_treatment    constr
_diffrn_measurement_device       KappaCCD
_computing_data_collection       'KappaCCD Software (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEPII (Johnson, 1976), PLATON (Spek, 2003) and MERCURY (CCDC, Cam.UK, 2004)
;
_computing_publication_material  'PLATON (Spek, 2003)'

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  all

_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.13988
_diffrn_orient_matrix_UB_12      -0.01776
_diffrn_orient_matrix_UB_13      -0.03019
_diffrn_orient_matrix_UB_21      -0.03705
_diffrn_orient_matrix_UB_22      0.02859
_diffrn_orient_matrix_UB_23      -0.09507
_diffrn_orient_matrix_UB_31      0.03373
_diffrn_orient_matrix_UB_32      0.10504
_diffrn_orient_matrix_UB_33      0.02077

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
?
;
_diffrn_radiation_type           ' MoK\a'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z

_cell_length_a                   6.7302(4)
_cell_length_b                   9.0666(6)
_cell_length_c                   9.8149(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     598.91(6)
_diffrn_reflns_number            1376
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_full        27.47
_cell_measurement_reflns_used    4295
_cell_measurement_theta_min      1.018
_cell_measurement_theta_max      27.485
_diffrn_measurement_method       CCD

_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_exptl_absorpt_coefficient_mu    0.436
_reflns_number_total             1354
_reflns_number_gt                889
_reflns_threshold_expression     >2sigma(I)

_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^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_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   0.07(11)
_refine_ls_number_reflns         1354
_chemical_absolute_configuration ad
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.891
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS/PLATON 2003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S6 S Uani 0.05598(10) -0.17315(6) 0.07446(6) 1.000 0.0531(2) . .
O7 O Uani 0.1277(3) -0.27459(19) 0.18329(18) 1.000 0.0760(7) . .
N1 N Uani 0.2738(3) 0.0474(2) -0.04046(17) 1.000 0.0516(7) . .
N4 N Uani 0.3143(3) 0.0334(2) 0.18177(16) 1.000 0.0497(7) . .
C2 C Uani 0.4065(3) 0.1536(3) 0.0020(3) 1.000 0.0559(9) . .
C3 C Uani 0.4337(4) 0.1451(3) 0.1388(2) 1.000 0.0516(9) . .
C5 C Uani 0.2215(3) -0.0212(2) 0.0720(2) 1.000 0.0429(7) . .
C8 C Uani -0.1540(4) -0.0773(3) 0.1394(3) 1.000 0.0751(11) . .
H2 H Uiso 0.46302 0.22045 -0.06326 1.000 0.0723 . .
H3 H Uiso 0.51241 0.19872 0.20358 1.000 0.0586 . .
H4 H Uiso 0.29206 -0.01312 0.25657 1.000 0.0649 . .
H8A H Uiso -0.20475 -0.01076 0.07175 1.000 0.0677 . .
H8B H Uiso -0.11435 -0.02246 0.21855 1.000 0.0677 . .
H8C H Uiso -0.25536 -0.14676 0.16405 1.000 0.0677 . .

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
S6 0.0638(4) 0.0490(3) 0.0466(3) -0.0061(3) -0.0022(3) -0.0020(3)
O7 0.1020(15) 0.0527(11) 0.0734(12) 0.0130(10) -0.0120(11) -0.0032(11)
N1 0.0579(12) 0.0589(12) 0.0381(10) 0.0015(9) 0.0026(9) -0.0005(11)
N4 0.0541(11) 0.0608(13) 0.0342(10) -0.0010(9) 0.0006(8) -0.0025(10)
C2 0.0603(16) 0.0591(16) 0.0483(13) 0.0035(12) 0.0046(12) -0.0034(15)
C3 0.0488(13) 0.0597(17) 0.0464(14) -0.0048(11) -0.0003(12) -0.0032(15)
C5 0.0470(12) 0.0467(12) 0.0350(10) -0.0026(12) -0.0031(11) 0.0047(10)
C8 0.0564(16) 0.070(2) 0.099(2) -0.0192(17) 0.0079(16) -0.0086(15)

#===============================================================================

# MOLECULAR GEOMETRY/PLATON 2003

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All esds are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

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
S6 O7 1.4899(19) . . yes
S6 C5 1.772(2) . . yes
S6 C8 1.777(3) . . yes
N1 C2 1.378(3) . . yes
N1 C5 1.315(3) . . yes
N4 C3 1.360(3) . . yes
N4 C5 1.340(3) . . yes
N4 H4 0.8598 . . yes
C2 C3 1.357(4) . . yes
C2 H2 0.9604 . . yes
C3 H3 0.9598 . . yes
C8 H8A 0.9600 . . yes
C8 H8B 0.9602 . . yes
C8 H8C 0.9594 . . yes

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
O7 S6 C5 106.62(10) . . . yes
O7 S6 C8 107.60(12) . . . yes
C5 S6 C8 97.16(11) . . . yes
C2 N1 C5 104.49(19) . . . yes
C3 N4 C5 107.53(16) . . . yes
C5 N4 H4 115.09 . . . no
C3 N4 H4 137.14 . . . no
N1 C2 C3 110.3(2) . . . yes
N4 C3 C2 105.6(2) . . . yes
N1 C5 N4 112.05(18) . . . yes
S6 C5 N1 123.20(15) . . . yes
S6 C5 N4 124.70(15) . . . yes
N1 C2 H2 119.74 . . . no
C3 C2 H2 129.95 . . . no
N4 C3 H3 119.86 . . . no
C2 C3 H3 134.51 . . . no
S6 C8 H8A 110.01 . . . no
S6 C8 H8B 108.81 . . . no
S6 C8 H8C 109.56 . . . no
H8A C8 H8B 109.45 . . . no
H8A C8 H8C 109.51 . . . no
H8B C8 H8C 109.48 . . . no

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
O7 S6 C5 N1 144.21(18) . . . . no
O7 S6 C5 N4 -32.8(2) . . . . no
C8 S6 C5 N1 -105.0(2) . . . . no
C8 S6 C5 N4 78.0(2) . . . . no
C2 N1 C5 N4 -0.8(2) . . . . no
C5 N1 C2 C3 1.0(3) . . . . no
C2 N1 C5 S6 -178.19(16) . . . . no
C3 N4 C5 N1 0.4(3) . . . . no
C5 N4 C3 C2 0.2(3) . . . . no
C3 N4 C5 S6 177.69(17) . . . . no
N1 C2 C3 N4 -0.8(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S6 C8 3.652(3) . 3_545 no
S6 H8C 3.1239 . 3_545 no
O7 N4 3.062(3) . . no
O7 C8 3.255(3) . 4_545 no
O7 C2 3.323(3) . 2_555 no
O7 H2 2.6081 . 2_555 no
O7 H4 2.7132 . . no
O7 H3 2.6754 . 4_645 no
O7 H8B 2.4469 . 4_545 no
N1 N4 2.202(2) . . no
N1 N4 2.885(2) . 2_554 no
N4 N1 2.885(2) . 2_555 no
N4 O7 3.062(3) . . no
N4 N1 2.202(2) . . no
N1 H4 2.0644 . 2_554 no
C2 O7 3.323(3) . 2_554 no
C3 C8 3.430(4) . 1_655 no
C8 O7 3.255(3) . 4_555 no
C8 S6 3.652(3) . 3_445 no
C8 C3 3.430(4) . 1_455 no
C2 H8A 3.0878 . 1_655 no
C2 H4 3.0349 . 2_554 no
C3 H8A 2.8898 . 1_655 no
C3 H8C 2.9574 . 4_555 no
H2 O7 2.6081 . 2_554 no
H3 O7 2.6754 . 4_655 no
H3 H8C 2.5775 . 4_555 no
H4 O7 2.7132 . . no
H4 N1 2.0644 . 2_555 no
H4 C2 3.0349 . 2_555 no
H8A C2 3.0878 . 1_455 no
H8A C3 2.8898 . 1_455 no
H8B O7 2.4469 . 4_555 no
H8C S6 3.1239 . 3_445 no
H8C C3 2.9574 . 4_545 no
H8C H3 2.5775 . 4_545 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N4 H4 N1 0.8600 2.0600 2.885(2) 159.00 2_555 yes
C8 H8B O7 0.9600 2.4500 3.255(3) 142.00 4_555 yes

#===End of Crystallographic Information File