# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Marino Petrini'
'Elisabetta Foresti'
'Gianni Palmieri'
'Roberto Profeta'

_publ_contact_author_name        'Prof Marino Petrini'
_publ_contact_author_address     
;
Dip. Scienze Chimiche
Università di Camerino
via S.Agostino, 1
Camerino
I-62032
ITALY
;

_publ_contact_author_email       MARINO.PETRINI@UNICAM.IT

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Highly diastereoselective addition of nitromethane
anion to chiral a-amidoalkylphenyl sulfones. Synthesis of optically
active a-amino acid derivatives.
;

data_pet
_database_code_CSD               216822

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 N O6 S'
_chemical_formula_weight         371.44

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           ?
_symmetry_space_group_name_H-M   ?

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                   9.9643(4)
_cell_length_b                   11.1330(4)
_cell_length_c                   17.3159(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1920.90(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9426
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25018
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.07
_reflns_number_total             5606
_reflns_number_gt                5339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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/[σ²(Fo²)+(0.0693P)²+0.0347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.00(4)
_refine_ls_number_reflns         5606
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
S1 S 0.59563(3) 0.94708(3) 0.104011(14) 0.03913(7) Uani 1 1 d . . .
N1 N 0.39018(9) 0.99252(8) 0.00823(5) 0.03498(17) Uani 1 1 d . . .
H1 H 0.4068 1.0590 -0.0132 0.050 Uiso 1 1 d . . .
O1 O 0.64636(10) 1.06699(10) 0.09299(6) 0.0537(2) Uani 1 1 d . . .
O2 O 0.68829(10) 0.84975(11) 0.11670(6) 0.0599(3) Uani 1 1 d . . .
O3 O 0.62389(8) 0.99849(8) -0.07957(5) 0.04396(19) Uani 1 1 d . . .
O4 O 0.50500(11) 0.91851(9) -0.17728(5) 0.0517(2) Uani 1 1 d . . .
O5 O 0.22356(9) 0.87794(8) 0.05885(6) 0.0505(2) Uani 1 1 d . . .
O6 O 0.18439(8) 1.06664(8) 0.01241(5) 0.04282(18) Uani 1 1 d . . .
C1 C 0.47935(8) 0.95074(8) 0.18002(4) 0.0397(2) Uani 1 1 d G . .
C2 C 0.41274(10) 1.05692(6) 0.19773(5) 0.0505(3) Uani 1 1 d G . .
H2 H 0.4296 1.1260 0.1692 0.076 Uiso 1 1 calc R . .
C3 C 0.32090(10) 1.05981(8) 0.25812(6) 0.0641(4) Uani 1 1 d G . .
H3 H 0.2763 1.1309 0.2700 0.096 Uiso 1 1 calc R . .
C4 C 0.29568(11) 0.95651(11) 0.30081(5) 0.0670(4) Uani 1 1 d G . .
H4 H 0.2342 0.9584 0.3412 0.100 Uiso 1 1 calc R . .
C5 C 0.36228(12) 0.85032(8) 0.28310(5) 0.0674(4) Uani 1 1 d G . .
H5 H 0.3454 0.7812 0.3117 0.101 Uiso 1 1 calc R . .
C6 C 0.45412(10) 0.84744(7) 0.22270(5) 0.0537(3) Uani 1 1 d G . .
H6 H 0.4987 0.7764 0.2109 0.080 Uiso 1 1 calc R . .
C7 C 0.49269(10) 0.90533(9) 0.02063(6) 0.03437(18) Uani 1 1 d . . .
H7 H 0.4486 0.8289 0.0327 0.052 Uiso 1 1 calc R . .
C8 C 0.58066(11) 0.88526(10) -0.05062(6) 0.0387(2) Uani 1 1 d . . .
H8 H 0.6582 0.8350 -0.0375 0.058 Uiso 1 1 calc R . .
C9 C 0.50113(15) 0.82916(11) -0.11852(7) 0.0494(3) Uani 1 1 d . . .
H91 H 0.5432 0.7554 -0.1360 0.074 Uiso 1 1 calc R . .
H92 H 0.4094 0.8119 -0.1034 0.074 Uiso 1 1 calc R . .
C10 C 0.61979(14) 0.99091(13) -0.16234(7) 0.0480(3) Uani 1 1 d . . .
C11 C 0.5977(3) 1.11365(15) -0.19502(10) 0.0749(5) Uani 1 1 d . . .
H111 H 0.5168 1.1471 -0.1738 0.112 Uiso 1 1 calc R . .
H112 H 0.5896 1.1084 -0.2502 0.112 Uiso 1 1 calc R . .
H113 H 0.6723 1.1643 -0.1820 0.112 Uiso 1 1 calc R . .
C12 C 0.74636(19) 0.9303(2) -0.19265(10) 0.0805(6) Uani 1 1 d . . .
H12A H 0.8226 0.9804 -0.1822 0.121 Uiso 1 1 calc R . .
H12B H 0.7384 0.9183 -0.2474 0.121 Uiso 1 1 calc R . .
H12C H 0.7578 0.8542 -0.1675 0.121 Uiso 1 1 calc R . .
C13 C 0.26014(10) 0.97102(9) 0.02944(6) 0.03464(19) Uani 1 1 d . . .
C14 C 0.03815(11) 1.06523(12) 0.02879(7) 0.0447(2) Uani 1 1 d . . .
C15 C 0.01402(16) 1.05436(16) 0.11481(9) 0.0600(3) Uani 1 1 d . . .
H151 H 0.0607 1.1176 0.1412 0.090 Uiso 1 1 calc R . .
H152 H 0.0464 0.9780 0.1326 0.090 Uiso 1 1 calc R . .
H153 H -0.0804 1.0605 0.1251 0.090 Uiso 1 1 calc R . .
C16 C -0.00625(16) 1.18727(15) -0.00061(12) 0.0688(4) Uani 1 1 d . . .
H161 H -0.0118 1.1855 -0.0559 0.103 Uiso 1 1 calc R . .
H162 H 0.0576 1.2471 0.0150 0.103 Uiso 1 1 calc R . .
H163 H -0.0927 1.2065 0.0205 0.103 Uiso 1 1 calc R . .
C17 C -0.02815(15) 0.96466(16) -0.01650(11) 0.0661(4) Uani 1 1 d . . .
H171 H -0.1237 0.9687 -0.0097 0.099 Uiso 1 1 calc R . .
H172 H 0.0042 0.8886 0.0019 0.099 Uiso 1 1 calc R . .
H173 H -0.0069 0.9731 -0.0703 0.099 Uiso 1 1 calc R . .


_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 O1 1.4402(10) . ?
S1 O2 1.4405(10) . ?
S1 C1 1.7539 . ?
S1 C7 1.8311(11) . ?
N1 C13 1.3678(13) . ?
N1 C7 1.4254(13) . ?
O3 C8 1.4233(14) . ?
O3 C10 1.4361(14) . ?
O4 C10 1.4230(16) . ?
O4 C9 1.4235(16) . ?
O5 C13 1.2108(13) . ?
O6 C13 1.3379(12) . ?
O6 C14 1.4846(13) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C7 C8 1.5298(15) . ?
C8 C9 1.5494(16) . ?
C10 C11 1.495(2) . ?
C10 C12 1.523(2) . ?
C14 C15 1.514(2) . ?
C14 C16 1.5170(18) . ?
C14 C17 1.518(2) . ?

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 O2 119.51(7) . . ?
O1 S1 C1 108.04(5) . . ?
O2 S1 C1 109.05(5) . . ?
O1 S1 C7 109.11(5) . . ?
O2 S1 C7 106.76(6) . . ?
C1 S1 C7 103.15(5) . . ?
C13 N1 C7 121.28(8) . . ?
C8 O3 C10 106.91(9) . . ?
C10 O4 C9 106.71(10) . . ?
C13 O6 C14 120.21(9) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 S1 120.05(5) . . ?
C6 C1 S1 119.95(5) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
N1 C7 C8 112.87(8) . . ?
N1 C7 S1 110.32(7) . . ?
C8 C7 S1 110.61(7) . . ?
O3 C8 C7 109.16(8) . . ?
O3 C8 C9 104.15(9) . . ?
C7 C8 C9 112.20(10) . . ?
O4 C9 C8 104.29(10) . . ?
O4 C10 O3 103.75(10) . . ?
O4 C10 C11 109.29(13) . . ?
O3 C10 C11 109.15(12) . . ?
O4 C10 C12 110.62(13) . . ?
O3 C10 C12 110.26(12) . . ?
C11 C10 C12 113.33(16) . . ?
O5 C13 O6 127.14(10) . . ?
O5 C13 N1 123.22(10) . . ?
O6 C13 N1 109.63(8) . . ?
O6 C14 C15 110.17(11) . . ?
O6 C14 C16 102.27(10) . . ?
C15 C14 C16 110.83(13) . . ?
O6 C14 C17 109.65(11) . . ?
C15 C14 C17 112.35(13) . . ?
C16 C14 C17 111.11(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.07
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.112


