# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Sean Bew'
'David L. Hughes'
'Vladimir Savic'
'Katy M. Soapi'
'Martin A. Wilson'

_publ_contact_author_name        'Sean Bew'
_publ_contact_author_address     
;
Department of Chemical Sciences
University of East Anglia
University Plain
Norwich
Norfolk
NR4 7TJ
UNITED KINGDOM
;

_publ_contact_author_email       S.BEW@UEA.AC.UK

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
expedient synthesis of substituted
(S)-N-(a-methylbenzyl)aziridines
;

data_martinw8
_database_code_depnum_ccdc_archive 'CCDC 606486'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Compound 14'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_structural     PhCHMe-cyclo-NCH2CH-SO2Ph
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.37
_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 0.0033 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 212121'

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

_cell_length_a                   8.587(3)
_cell_length_b                   11.452(2)
_cell_length_c                   15.080(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1483.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      12

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'EMPABS, (Sheldrick et al, 1977)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Nonius CAD4 diffractometer'
_diffrn_measurement_method       'scintillation counter; \w/\q scans'
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  '10000 s'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2573
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2394
_reflns_number_gt                2189
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'CAD4/EXPRESS (Enraf-Nonius, 1992)'
_computing_cell_refinement       'CAD4/EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'CAD4 (Hursthouse, 1976)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0534P)^2^+0.1111P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_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'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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
N1 N 0.33981(18) 0.39955(14) 0.30583(11) 0.0435(4) Uani 1 1 d . . .
C1 C 0.2601(2) 0.36953(19) 0.22148(13) 0.0471(5) Uani 1 1 d . . .
H1 H 0.2619 0.4378 0.1823 0.057 Uiso 1 1 calc R . .
C11 C 0.0934(2) 0.33817(17) 0.24130(13) 0.0425(4) Uani 1 1 d . . .
C12 C -0.0284(3) 0.3890(2) 0.19618(17) 0.0612(6) Uani 1 1 d . . .
H12 H -0.0079 0.4436 0.1521 0.073 Uiso 1 1 calc R . .
C13 C -0.1809(3) 0.3597(3) 0.21559(19) 0.0737(8) Uani 1 1 d . . .
H13 H -0.2617 0.3941 0.1839 0.088 Uiso 1 1 calc R . .
C14 C -0.2140(3) 0.2810(2) 0.28075(16) 0.0621(6) Uani 1 1 d . . .
H14 H -0.3169 0.2637 0.2948 0.075 Uiso 1 1 calc R . .
C15 C -0.0961(3) 0.2283(2) 0.32480(17) 0.0637(6) Uani 1 1 d . . .
H15 H -0.1180 0.1735 0.3686 0.076 Uiso 1 1 calc R . .
C16 C 0.0578(3) 0.2560(2) 0.30482(17) 0.0611(6) Uani 1 1 d . . .
H16 H 0.1379 0.2183 0.3349 0.073 Uiso 1 1 calc R . .
C17 C 0.3489(3) 0.2707(3) 0.17761(17) 0.0681(7) Uani 1 1 d . . .
H17A H 0.4540 0.2951 0.1662 0.102 Uiso 1 1 calc R . .
H17B H 0.2993 0.2504 0.1227 0.102 Uiso 1 1 calc R . .
H17C H 0.3497 0.2040 0.2162 0.102 Uiso 1 1 calc R . .
C2 C 0.3107(2) 0.51748(16) 0.33610(12) 0.0446(4) Uani 1 1 d . . .
H2 H 0.2411 0.5652 0.2995 0.054 Uiso 1 1 calc R . .
S2 S 0.30048(6) 0.53913(4) 0.45228(3) 0.04683(14) Uani 1 1 d . . .
O21 O 0.40813(17) 0.46048(16) 0.49419(10) 0.0600(4) Uani 1 1 d . . .
O22 O 0.3171(2) 0.66212(14) 0.46638(12) 0.0698(5) Uani 1 1 d . . .
C21 C 0.1091(2) 0.49733(17) 0.48184(13) 0.0438(4) Uani 1 1 d . . .
C22 C 0.0835(3) 0.38802(19) 0.51638(15) 0.0508(5) Uani 1 1 d . . .
H22 H 0.1659 0.3364 0.5242 0.061 Uiso 1 1 calc R . .
C23 C -0.0673(3) 0.3554(2) 0.53956(16) 0.0583(5) Uani 1 1 d . . .
H23 H -0.0865 0.2820 0.5635 0.070 Uiso 1 1 calc R . .
C24 C -0.1874(3) 0.4326(2) 0.52678(16) 0.0618(6) Uani 1 1 d . . .
H24 H -0.2883 0.4104 0.5415 0.074 Uiso 1 1 calc R . .
C25 C -0.1611(3) 0.5412(2) 0.49290(18) 0.0662(6) Uani 1 1 d . . .
H25 H -0.2440 0.5923 0.4847 0.079 Uiso 1 1 calc R . .
C26 C -0.0111(3) 0.5757(2) 0.47059(17) 0.0590(6) Uani 1 1 d . . .
H26 H 0.0079 0.6502 0.4485 0.071 Uiso 1 1 calc R . .
C3 C 0.4633(2) 0.4871(2) 0.29709(17) 0.0567(5) Uani 1 1 d . . .
H3A H 0.4868 0.5162 0.2382 0.068 Uiso 1 1 calc R . .
H3B H 0.5521 0.4814 0.3366 0.068 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
N1 0.0357(8) 0.0476(8) 0.0472(8) 0.0017(7) -0.0041(7) 0.0001(7)
C1 0.0424(10) 0.0570(11) 0.0419(9) 0.0033(9) -0.0033(8) 0.0009(9)
C11 0.0405(9) 0.0473(9) 0.0398(9) -0.0012(8) -0.0054(8) -0.0020(8)
C12 0.0472(11) 0.0762(15) 0.0603(11) 0.0238(13) -0.0008(11) 0.0053(12)
C13 0.0418(12) 0.102(2) 0.0772(16) 0.0261(15) -0.0018(12) 0.0071(14)
C14 0.0447(11) 0.0762(14) 0.0655(13) -0.0038(12) -0.0010(11) -0.0125(12)
C15 0.0644(15) 0.0659(14) 0.0607(13) 0.0159(12) -0.0038(12) -0.0169(13)
C16 0.0516(12) 0.0696(14) 0.0620(13) 0.0231(12) -0.0144(12) -0.0077(12)
C17 0.0548(13) 0.0870(17) 0.0626(13) -0.0209(13) 0.0010(12) 0.0089(13)
C2 0.0407(9) 0.0466(10) 0.0465(9) 0.0059(8) 0.0005(8) -0.0019(9)
S2 0.0428(2) 0.0496(2) 0.0481(2) -0.0020(2) -0.0032(2) -0.0069(2)
O21 0.0434(7) 0.0803(10) 0.0563(8) 0.0080(9) -0.0112(7) 0.0003(8)
O22 0.0714(11) 0.0571(8) 0.0809(11) -0.0142(8) 0.0096(11) -0.0173(9)
C21 0.0441(10) 0.0452(9) 0.0421(8) -0.0033(8) 0.0009(8) -0.0022(9)
C22 0.0459(10) 0.0473(10) 0.0593(11) 0.0041(10) -0.0012(10) 0.0025(9)
C23 0.0565(12) 0.0535(11) 0.0648(13) 0.0084(11) 0.0061(12) -0.0053(10)
C24 0.0444(11) 0.0762(14) 0.0649(13) 0.0055(11) 0.0098(11) -0.0006(11)
C25 0.0489(12) 0.0728(14) 0.0771(15) 0.0135(14) 0.0082(12) 0.0164(12)
C26 0.0558(13) 0.0511(11) 0.0701(14) 0.0112(11) 0.0044(12) 0.0061(10)
C3 0.0410(10) 0.0685(14) 0.0605(11) -0.0037(11) 0.0053(10) -0.0130(10)

_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
N1 C2 1.447(2) . ?
N1 C3 1.465(3) . ?
N1 C1 1.485(3) . ?
C1 C11 1.506(3) . ?
C1 C17 1.517(3) . ?
C1 H1 0.9800 . ?
C11 C12 1.377(3) . ?
C11 C16 1.377(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.353(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C2 C3 1.478(3) . ?
C2 S2 1.772(2) . ?
C2 H2 0.9800 . ?
S2 O22 1.4316(17) . ?
S2 O21 1.4372(17) . ?
S2 C21 1.769(2) . ?
C21 C22 1.374(3) . ?
C21 C26 1.378(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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 N1 C3 60.98(14) . . ?
C2 N1 C1 113.99(16) . . ?
C3 N1 C1 114.53(17) . . ?
N1 C1 C11 108.88(16) . . ?
N1 C1 C17 108.33(17) . . ?
C11 C1 C17 112.74(19) . . ?
N1 C1 H1 108.9 . . ?
C11 C1 H1 108.9 . . ?
C17 C1 H1 108.9 . . ?
C12 C11 C16 117.6(2) . . ?
C12 C11 C1 121.56(18) . . ?
C16 C11 C1 120.79(19) . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.1(2) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C2 C3 60.10(13) . . ?
N1 C2 S2 116.81(13) . . ?
C3 C2 S2 118.08(16) . . ?
N1 C2 H2 116.6 . . ?
C3 C2 H2 116.6 . . ?
S2 C2 H2 116.6 . . ?
O22 S2 O21 119.17(12) . . ?
O22 S2 C21 108.74(11) . . ?
O21 S2 C21 108.50(10) . . ?
O22 S2 C2 106.24(10) . . ?
O21 S2 C2 108.37(10) . . ?
C21 S2 C2 104.92(10) . . ?
C22 C21 C26 121.4(2) . . ?
C22 C21 S2 119.39(16) . . ?
C26 C21 S2 119.23(16) . . ?
C21 C22 C23 119.2(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 121.1(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 118.6(2) . . ?
C21 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
N1 C3 C2 58.91(13) . . ?
N1 C3 H3A 117.9 . . ?
C2 C3 H3A 117.9 . . ?
N1 C3 H3B 117.9 . . ?
C2 C3 H3B 117.9 . . ?
H3A C3 H3B 115.0 . . ?

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
C2 N1 C1 C11 -81.0(2) . . . . ?
C3 N1 C1 C11 -148.61(17) . . . . ?
C2 N1 C1 C17 156.10(18) . . . . ?
C3 N1 C1 C17 88.5(2) . . . . ?
N1 C1 C11 C12 128.9(2) . . . . ?
C17 C1 C11 C12 -110.8(2) . . . . ?
N1 C1 C11 C16 -52.0(3) . . . . ?
C17 C1 C11 C16 68.3(3) . . . . ?
C16 C11 C12 C13 1.3(4) . . . . ?
C1 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C13 C14 C15 -2.2(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C12 C11 C16 C15 -2.2(4) . . . . ?
C1 C11 C16 C15 178.6(2) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?
C1 N1 C2 C3 -105.82(19) . . . . ?
C3 N1 C2 S2 -108.52(18) . . . . ?
C1 N1 C2 S2 145.65(15) . . . . ?
N1 C2 S2 O22 163.51(15) . . . . ?
C3 C2 S2 O22 94.82(18) . . . . ?
N1 C2 S2 O21 34.34(18) . . . . ?
C3 C2 S2 O21 -34.35(19) . . . . ?
N1 C2 S2 C21 -81.41(16) . . . . ?
C3 C2 S2 C21 -150.10(16) . . . . ?
O22 S2 C21 C22 -147.86(17) . . . . ?
O21 S2 C21 C22 -16.85(19) . . . . ?
C2 S2 C21 C22 98.81(17) . . . . ?
O22 S2 C21 C26 31.4(2) . . . . ?
O21 S2 C21 C26 162.44(17) . . . . ?
C2 S2 C21 C26 -81.89(19) . . . . ?
C26 C21 C22 C23 0.7(3) . . . . ?
S2 C21 C22 C23 180.00(19) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -0.9(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C22 C21 C26 C25 -1.6(4) . . . . ?
S2 C21 C26 C25 179.1(2) . . . . ?
C24 C25 C26 C21 1.3(4) . . . . ?
C1 N1 C3 C2 104.95(18) . . . . ?
S2 C2 C3 N1 106.44(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049