# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Rajender Reddy Leleti'
_publ_contact_author_email       RAJENDER.LELETI@NOVARTIS.COM

_publ_section_title              
;
Asymmetric Synthesis of 2-Substituted Pyrrolidines
by Addition of Grignard Reagents to ?-Chlorinated N-tert-Butanesulfinyl
Imine
;
loop_
_publ_author_name
'Rajender Reddy Leleti'
'Mahavir Prashad'

# Attachment 'reddy1full.cif'

#============================================================================
data_REDDY1
_database_code_depnum_ccdc_archive 'CCDC 747534'
#TrackingRef 'reddy1full.cif'

# 5. CRYSTAL DATA

_chemical_compound_source        ?
_exptl_crystal_description       chunk
_exptl_crystal_colour_primary    colourless
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_chemical_name_systematic        
; ?
;
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H20 Br1 N1 O1 S1'
_chemical_formula_moiety         'C14 H20 Br1 N1 O1 S1'
_chemical_formula_structural     ?
_chemical_formula_weight         330.29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1888(4)
_cell_length_b                   10.0920(6)
_cell_length_c                   24.6826(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1541.61(17)
_cell_measurement_reflns_used    3679
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_formula_units_z            4
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'

loop_
_atom_type_symbol
_atom_type_radius_bond
Br 1.14
S 1.02
O 0.73
N 0.75
C 0.77
H 0.32

_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    1.954
_cell_measurement_temperature    298(2)
_exptl_crystal_F_000             680

# 6. DATA COLLECTION

_diffrn_ambient_temperature      298
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.7432
_exptl_absorpt_correction_T_max  0.9922
_diffrn_reflns_number            3679
_diffrn_measured_fraction_theta_max 0.9415
_diffrn_reflns_theta_full        23.0
_diffrn_measured_fraction_theta_full 0.9855
_reflns_number_total             3654
_reflns_Friedel_coverage         0.7767
_reflns_number_gt                2390
_reflns_threshold_expression     >2.0\s(I)
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_max       35
_diffrn_special_details          'mosaicity from Denzo/Scalepack is 0.00'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

# 7. REFINEMENT DATA

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors. Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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_R_factor_all          0.071
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.077
_refine_ls_wR_factor_gt          0.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_weighting_scheme      'calc '
_refine_ls_weighting_details     
'1/[\s^2^(Fo^2^)+(0.0201P)^2^+0.1612P] where P=(Fo^2^+2Fc^2^)/3 '

_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.066(9)
_atom_type_scat_source           
'International Tables for Crystallography (Vol C)'

# 8. COMPUTING DATA

_computing_data_collection       'Collect (Nonius, 1998)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_structure_solution    
;
Direct methods (SIR2004, Burla et al., 2005)
;
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP (Johnson, 1976)
PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'

# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br24 Br 0.47893(6) 0.97402(3) 0.646145(15) 0.08731(15) Uani 1 1 d . . .
S1 S -0.11138(11) 1.69274(6) 0.62629(3) 0.05570(19) Uani 1 1 d . . .
O1 O -0.3377(3) 1.6617(2) 0.61109(9) 0.0741(6) Uani 1 1 d . . .
N1 N 0.0585(3) 1.59616(19) 0.59136(8) 0.0511(6) Uani 1 1 d . . .
C2 C -0.0232(4) 1.4693(2) 0.56910(11) 0.0558(6) Uani 1 1 d . . .
H2 H -0.1761 1.4590 0.5785 0.067 Uiso 1 1 calc R . .
C3 C -0.0013(6) 1.4880(3) 0.50795(12) 0.0794(9) Uani 1 1 d . . .
H3A H 0.0165 1.4035 0.4897 0.095 Uiso 1 1 calc R . .
H3B H -0.1266 1.5329 0.4931 0.095 Uiso 1 1 calc R . .
C4 C 0.1997(6) 1.5725(4) 0.50241(13) 0.0832(10) Uani 1 1 d . . .
H4A H 0.3294 1.5191 0.5058 0.100 Uiso 1 1 calc R . .
H4B H 0.2020 1.6182 0.4678 0.100 Uiso 1 1 calc R . .
C5 C 0.1808(5) 1.6691(3) 0.54859(12) 0.0660(8) Uani 1 1 d . . .
H5A H 0.3225 1.6948 0.5617 0.079 Uiso 1 1 calc R . .
H5B H 0.1032 1.7480 0.5374 0.079 Uiso 1 1 calc R . .
C11 C -0.0811(4) 1.6325(3) 0.69629(11) 0.0549(7) Uani 1 1 d . . .
C12 C 0.1558(5) 1.6425(4) 0.71163(15) 0.0777(10) Uani 1 1 d . . .
H12A H 0.2069 1.7305 0.7044 0.117 Uiso 1 1 calc R . .
H12B H 0.2378 1.5800 0.6907 0.117 Uiso 1 1 calc R . .
H12C H 0.1724 1.6233 0.7495 0.117 Uiso 1 1 calc R . .
C13 C -0.1708(5) 1.4925(3) 0.70230(13) 0.0709(9) Uani 1 1 d . . .
H13A H -0.1792 1.4700 0.7400 0.106 Uiso 1 1 calc R . .
H13B H -0.0771 1.4311 0.6841 0.106 Uiso 1 1 calc R . .
H13C H -0.3124 1.4883 0.6865 0.106 Uiso 1 1 calc R . .
C14 C -0.2167(6) 1.7304(3) 0.72937(14) 0.0729(9) Uani 1 1 d . . .
H14A H -0.3664 1.7205 0.7200 0.109 Uiso 1 1 calc R . .
H14B H -0.1709 1.8192 0.7215 0.109 Uiso 1 1 calc R . .
H14C H -0.1977 1.7127 0.7673 0.109 Uiso 1 1 calc R . .
C21 C 0.1029(4) 1.3505(2) 0.58968(11) 0.0516(6) Uani 1 1 d . . .
C22 C 0.0124(5) 1.2252(2) 0.58572(11) 0.0617(7) Uani 1 1 d . . .
H22 H -0.1252 1.2162 0.5710 0.074 Uiso 1 1 calc R . .
C23 C 0.1215(5) 1.1131(3) 0.60304(12) 0.0677(8) Uani 1 1 d . . .
H23 H 0.0570 1.0301 0.6009 0.081 Uiso 1 1 calc R . .
C24 C 0.3259(5) 1.1269(3) 0.62332(12) 0.0599(7) Uani 1 1 d . . .
C25 C 0.4215(4) 1.2487(2) 0.62743(12) 0.0578(7) Uani 1 1 d . . .
H25 H 0.5602 1.2565 0.6416 0.069 Uiso 1 1 calc R . .
C26 C 0.3096(4) 1.3609(3) 0.61027(11) 0.0542(7) Uani 1 1 d . . .
H26 H 0.3748 1.4437 0.6127 0.065 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
Br24 0.1099(3) 0.06036(17) 0.0917(3) 0.01523(17) 0.0153(2) 0.02941(19)
S1 0.0606(4) 0.0449(3) 0.0616(4) 0.0052(3) -0.0057(4) 0.0093(3)
O1 0.0539(12) 0.0877(14) 0.0806(16) -0.0016(12) -0.0163(10) 0.0200(11)
N1 0.0528(14) 0.0471(11) 0.0534(14) 0.0022(10) 0.0001(10) 0.0010(10)
C2 0.0516(15) 0.0538(13) 0.0621(17) -0.0031(13) -0.0036(13) 0.0016(15)
C3 0.101(3) 0.0791(19) 0.0583(18) -0.0050(15) -0.0194(18) 0.012(2)
C4 0.093(2) 0.098(2) 0.059(2) 0.0146(19) 0.0080(17) 0.003(2)
C5 0.0644(19) 0.0714(19) 0.062(2) 0.0143(17) 0.0021(14) -0.0027(15)
C11 0.0562(17) 0.0533(15) 0.0551(17) 0.0018(13) -0.0038(13) 0.0069(13)
C12 0.065(2) 0.096(2) 0.072(2) -0.002(2) -0.0122(16) 0.0088(18)
C13 0.089(2) 0.0562(17) 0.068(2) 0.0096(15) 0.0027(16) -0.0029(16)
C14 0.076(2) 0.075(2) 0.068(2) -0.0108(17) 0.0057(17) 0.0101(17)
C21 0.0519(16) 0.0454(13) 0.0574(17) -0.0056(12) 0.0009(13) 0.0027(12)
C22 0.0544(16) 0.0562(15) 0.0744(19) -0.0129(13) -0.0013(16) -0.0027(15)
C23 0.077(2) 0.0457(15) 0.080(2) -0.0078(15) 0.0135(18) -0.0027(15)
C24 0.073(2) 0.0504(14) 0.0558(18) 0.0009(13) 0.0135(15) 0.0123(14)
C25 0.0604(17) 0.0555(14) 0.0574(18) 0.0005(13) 0.0023(14) 0.0052(13)
C26 0.0548(17) 0.0480(14) 0.0597(19) -0.0007(13) 0.0021(14) 0.0017(13)

# 10. 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_1
_geom_bond_publ_flag
Br24 C24 1.896(3) . ?
S1 O1 1.483(2) . ?
S1 N1 1.673(2) . ?
S1 C11 1.841(3) . ?
N1 C2 1.482(3) . ?
N1 C5 1.493(3) . ?
C2 C21 1.518(3) . ?
C2 C3 1.527(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.514(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.505(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C12 1.518(4) . ?
C11 C13 1.525(4) . ?
C11 C14 1.531(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 C26 1.380(4) . ?
C21 C22 1.386(3) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(4) . ?
C25 C26 1.394(4) . ?
C25 H25 0.9300 . ?
C26 H26 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
O1 S1 N1 109.89(12) . . ?
O1 S1 C11 105.29(13) . . ?
N1 S1 C11 103.15(11) . . ?
C2 N1 C5 109.7(2) . . ?
C2 N1 S1 118.69(18) . . ?
C5 N1 S1 113.30(17) . . ?
N1 C2 C21 112.5(2) . . ?
N1 C2 C3 103.3(2) . . ?
C21 C2 C3 112.5(2) . . ?
N1 C2 H2 109.5 . . ?
C21 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C4 C3 C2 103.4(2) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C3 103.5(3) . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
N1 C5 C4 104.8(2) . . ?
N1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C12 C11 C13 112.9(3) . . ?
C12 C11 C14 110.7(3) . . ?
C13 C11 C14 110.3(3) . . ?
C12 C11 S1 108.1(2) . . ?
C13 C11 S1 111.1(2) . . ?
C14 C11 S1 103.42(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 C21 C22 118.0(3) . . ?
C26 C21 C2 122.6(2) . . ?
C22 C21 C2 119.3(2) . . ?
C23 C22 C21 121.7(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C24 C23 C22 118.7(3) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C25 C24 C23 121.2(3) . . ?
C25 C24 Br24 119.5(2) . . ?
C23 C24 Br24 119.2(2) . . ?
C24 C25 C26 119.5(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 120.7(3) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?

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
O1 S1 N1 C2 -22.6(2) . . . . ?
C11 S1 N1 C2 89.22(19) . . . . ?
O1 S1 N1 C5 108.2(2) . . . . ?
C11 S1 N1 C5 -140.0(2) . . . . ?
C5 N1 C2 C21 105.8(2) . . . . ?
S1 N1 C2 C21 -121.8(2) . . . . ?
C5 N1 C2 C3 -15.8(3) . . . . ?
S1 N1 C2 C3 116.7(2) . . . . ?
N1 C2 C3 C4 33.8(3) . . . . ?
C21 C2 C3 C4 -87.7(3) . . . . ?
C2 C3 C4 C5 -39.5(3) . . . . ?
C2 N1 C5 C4 -8.6(3) . . . . ?
S1 N1 C5 C4 -143.7(2) . . . . ?
C3 C4 C5 N1 29.6(3) . . . . ?
O1 S1 C11 C12 171.7(2) . . . . ?
N1 S1 C11 C12 56.5(2) . . . . ?
O1 S1 C11 C13 47.4(2) . . . . ?
N1 S1 C11 C13 -67.8(2) . . . . ?
O1 S1 C11 C14 -70.9(2) . . . . ?
N1 S1 C11 C14 173.9(2) . . . . ?
N1 C2 C21 C26 -21.3(4) . . . . ?
C3 C2 C21 C26 94.9(3) . . . . ?
N1 C2 C21 C22 161.6(2) . . . . ?
C3 C2 C21 C22 -82.3(3) . . . . ?
C26 C21 C22 C23 1.7(4) . . . . ?
C2 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 -1.6(5) . . . . ?
C22 C23 C24 C25 1.0(5) . . . . ?
C22 C23 C24 Br24 -179.0(2) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
Br24 C24 C25 C26 179.5(2) . . . . ?
C22 C21 C26 C25 -1.2(4) . . . . ?
C2 C21 C26 C25 -178.3(3) . . . . ?
C24 C25 C26 C21 0.6(4) . . . . ?