# 1. SUBMISSION DETAILS

_publ_contact_author           # Name and address of author for correspondence
;       Maxim A. Voinov
        North Carolina State University
        College of Physical and
        Mathematical Sciences
        Campus Box 8204
        Raleigh, NC 27695-8204
        USA
;
_publ_contact_author_phone        '(919) 515 3209'
_publ_contact_author_fax          '(919) 513 7353'
_publ_contact_author_email        mvoynov@ncsu.edu
   
_publ_requested_journal           ?
_publ_requested_coeditor_name     ?

_publ_contact_letter
; Please consider this CIF submission for deposition in the Cambridge
  Structural Database.
;

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

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic     ?
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted            ?
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code            ?
_journal_coeditor_notes
; ?
;
_journal_techeditor_code          ?
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM               ?
_journal_name_full                ?
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

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

# 3. TITLE AND AUTHOR LIST

_publ_section_title
;

;

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

loop_
	_publ_author_name
	_publ_author_address
 'Voinov, Maxim A.'                #<--'Last name, first name' 
;    North Carolina State University
     College of Physical and
     Mathematical Sciences
     Campus Box 8204
     Raleigh, NC 27695-8204
     USA
;
  'Shevelev, Tikhon G.'               
;    Novosibirsk Institute of Organic Chemistry 
     Ave. akad. Lavrent'eva 9 
     630090 Novosibirsk 
     Russia
;
  'Rybalova, Tatyana V.'
;    Novosibirsk Institute of Organic Chemistry 
     Ave. akad. Lavrent'eva 9 
     630090 Novosibirsk 
     Russia
;
  'Gatilov, Yury V.'
;    Novosibirsk Institute of Organic Chemistry 
     Ave. akad. Lavrent'eva 9 
     630090 Novosibirsk 
     Russia
;
  'Pervukhina, Natalie V.'
;    Institute of Inorganic Chemistry, 
     Ave. akad. Lavrent'eva 5,  
     630090 Novosibirsk 
     Russia
;
  'Burdukov, Aleksei B.'
;    Institute of Inorganic Chemistry, 
     Ave. akad. Lavrent'eva 5,  
     630090 Novosibirsk
     Russia 
;
  'Grigor'ev, Igor A.'
;    Novosibirsk Institute of Organic Chemistry 
     Ave. akad. Lavrent'eva 9 
     630090 Novosibirsk 
     Russia
;
#==============================================================================

# 4. TEXT

_publ_section_abstract
; 	

;
_publ_section_comment
;

;
_publ_section_exptl_prep
;

;
_publ_section_exptl_refinement
;
  
;
_publ_section_references
;
  
;
_publ_section_figure_captions
; 

;
_publ_section_acknowledgements
; 

;

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

# 5. CHEMICAL DATA

data_compound_9i_Voinov 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 2,2,4,4-Tetramethyl-5-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyrrole 1-oxide 
; 
_chemical_name_common             ? 
_chemical_melting_point           523 
_chemical_formula_moiety          'C15 H21 N O3 S' 
_chemical_formula_sum 
 'C15 H21 N O3 S' 
_chemical_formula_weight          295.39 
 
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            'Monoclinic' 
_symmetry_space_group_name_H-M    'P 21/n'     
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    6.5914(9) 
_cell_length_b                    27.895(4) 
_cell_length_c                    8.8022(12) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.128(15) 
_cell_angle_gamma                 90.00 
_cell_volume                      1617.3(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     36   
_cell_measurement_theta_min       12.2 
_cell_measurement_theta_max       13.0 
 
_exptl_crystal_description        'elongated prism' 
_exptl_crystal_colour             'colorless'       
_exptl_crystal_size_max           1.00 
_exptl_crystal_size_mid           0.17 
_exptl_crystal_size_min           0.17 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.213 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     0.206 
_exptl_absorpt_correction_type    'integration' 
_exptl_absorpt_correction_T_min   0.9222        
_exptl_absorpt_correction_T_max   0.9760        
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
  Melting point grater 523 K from hexane:EtOAc 4:1
; 
 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker P4'    
_diffrn_measurement_method        '2\q/\w scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         3.0
_diffrn_reflns_number             3073 
_diffrn_reflns_av_R_equivalents   0.0150 
_diffrn_reflns_av_sigmaI/netI     0.0302 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -33 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.43 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              2817 
_reflns_number_gt                 2338 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker XSCANS'  
_computing_cell_refinement        'Bruker XSCANS'  
_computing_data_reduction         'Bruker SHELXTL' 
_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 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^)+(0.0772P)^2^+0.5329P] 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_number_reflns          2817 
_refine_ls_number_parameters      181 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0593 
_refine_ls_R_factor_gt            0.0494 
_refine_ls_wR_factor_ref          0.1436 
_refine_ls_wR_factor_gt           0.1346 
_refine_ls_goodness_of_fit_ref    1.047 
_refine_ls_restrained_S_all       1.047 
_refine_ls_shift/su_max           0.004 
_refine_ls_shift/su_mean          0.001 
 
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_symetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S 0.55908(8) 0.158749(19) 0.01872(6) 0.0476(2) Uani 1 1 d . . . 
O1 O 0.4147(4) 0.09173(6) -0.2255(2) 0.0828(6) Uani 1 1 d . . . 
O2 O 0.3492(3) 0.15271(7) 0.0494(2) 0.0657(5) Uani 1 1 d . . . 
O3 O 0.6644(3) 0.19944(6) 0.0821(2) 0.0699(5) Uani 1 1 d . . . 
N1 N 0.5087(3) 0.12888(6) -0.2655(2) 0.0541(5) Uani 1 1 d . . . 
C5 C 0.5855(3) 0.16240(7) -0.1793(2) 0.0465(5) Uani 1 1 d . . . 
C4 C 0.6947(4) 0.20125(9) -0.2637(3) 0.0668(7) Uani 1 1 d . . . 
C3 C 0.6477(7) 0.18501(15) -0.4295(4) 0.1187(15) Uani 1 1 d . . . 
H3A H 0.5604 0.2084 -0.4804 0.142 Uiso 1 1 calc R . . 
H3B H 0.7731 0.1832 -0.4835 0.142 Uiso 1 1 calc R . . 
C2 C 0.5456(4) 0.13703(10) -0.4334(3) 0.0666(7) Uani 1 1 d . . . 
C9 C 0.9212(5) 0.20142(12) -0.2226(4) 0.0905(10) Uani 1 1 d . . . 
H9A H 0.9771 0.1704 -0.2425 0.136 Uiso 1 1 calc R . . 
H9B H 0.9418 0.2090 -0.1168 0.136 Uiso 1 1 calc R . . 
H9C H 0.9875 0.2250 -0.2827 0.136 Uiso 1 1 calc R . . 
C8 C 0.6031(6) 0.25074(11) -0.2356(5) 0.1078(13) Uani 1 1 d . . . 
H8A H 0.4606 0.2501 -0.2624 0.162 Uiso 1 1 calc R . . 
H8B H 0.6690 0.2741 -0.2967 0.162 Uiso 1 1 calc R . . 
H8C H 0.6221 0.2590 -0.1302 0.162 Uiso 1 1 calc R . . 
C7 C 0.6800(9) 0.09727(17) -0.4834(4) 0.160(2) Uani 1 1 d . . . 
H7A H 0.6066 0.0676 -0.4826 0.241 Uiso 1 1 calc R . . 
H7B H 0.7969 0.0951 -0.4154 0.241 Uiso 1 1 calc R . . 
H7C H 0.7229 0.1037 -0.5845 0.241 Uiso 1 1 calc R . . 
C6 C 0.3433(6) 0.13757(18) -0.5161(4) 0.1146(13) Uani 1 1 d . . . 
H6A H 0.2874 0.1058 -0.5179 0.172 Uiso 1 1 calc R . . 
H6B H 0.3593 0.1485 -0.6184 0.172 Uiso 1 1 calc R . . 
H6C H 0.2534 0.1588 -0.4652 0.172 Uiso 1 1 calc R . . 
C10 C 0.6934(3) 0.10705(7) 0.0765(2) 0.0434(5) Uani 1 1 d . . . 
C11 C 0.5926(3) 0.06387(8) 0.0920(2) 0.0512(5) Uani 1 1 d . . . 
H11A H 0.4551 0.0615 0.0653 0.061 Uiso 1 1 calc R . . 
C12 C 0.6974(4) 0.02452(8) 0.1471(3) 0.0598(6) Uani 1 1 d . . . 
H12A H 0.6293 -0.0044 0.1583 0.072 Uiso 1 1 calc R . . 
C13 C 0.9018(4) 0.02717(9) 0.1861(3) 0.0608(6) Uani 1 1 d . . . 
C14 C 1.0004(4) 0.07090(10) 0.1678(3) 0.0660(7) Uani 1 1 d . . . 
H14A H 1.1383 0.0732 0.1929 0.079 Uiso 1 1 calc R . . 
C15 C 0.8989(3) 0.11060(9) 0.1136(3) 0.0570(6) Uani 1 1 d . . . 
H15A H 0.9670 0.1395 0.1019 0.068 Uiso 1 1 calc R . . 
C16 C 1.0166(6) -0.01585(11) 0.2482(4) 0.0911(10) Uani 1 1 d . . . 
H16A H 0.9262 -0.0428 0.2529 0.137 Uiso 1 1 calc R . . 
H16B H 1.0710 -0.0087 0.3483 0.137 Uiso 1 1 calc R . . 
H16C H 1.1255 -0.0234 0.1828 0.137 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 0.0509(4) 0.0508(3) 0.0415(3) -0.0086(2) 0.0084(2) -0.0019(2) 
O1 0.1353(18) 0.0635(11) 0.0488(9) 0.0043(8) -0.0089(10) -0.0451(11) 
O2 0.0507(10) 0.0860(12) 0.0616(10) 0.0000(8) 0.0186(8) 0.0067(8) 
O3 0.0825(13) 0.0557(10) 0.0710(11) -0.0248(8) -0.0057(9) -0.0031(8) 
N1 0.0743(13) 0.0517(10) 0.0365(9) 0.0033(8) 0.0055(8) -0.0057(9) 
C5 0.0517(12) 0.0448(11) 0.0431(11) 0.0026(9) 0.0050(9) -0.0055(9) 
C4 0.0693(17) 0.0639(15) 0.0673(16) 0.0237(12) 0.0050(12) -0.0158(12) 
C3 0.156(4) 0.139(3) 0.0620(19) 0.035(2) 0.009(2) -0.056(3) 
C2 0.0931(19) 0.0734(16) 0.0336(11) 0.0074(11) 0.0066(11) 0.0139(14) 
C9 0.0708(19) 0.103(2) 0.099(2) 0.0284(19) 0.0187(16) -0.0269(17) 
C8 0.117(3) 0.0580(18) 0.148(4) 0.036(2) -0.005(2) -0.0031(17) 
C7 0.264(6) 0.159(4) 0.061(2) 0.011(2) 0.045(3) 0.120(4) 
C6 0.117(3) 0.173(4) 0.0525(17) 0.022(2) -0.0187(18) -0.015(3) 
C10 0.0456(12) 0.0511(12) 0.0341(10) -0.0051(8) 0.0072(8) -0.0059(9) 
C11 0.0510(13) 0.0574(13) 0.0452(11) -0.0042(10) 0.0019(9) -0.0140(10) 
C12 0.0741(17) 0.0534(13) 0.0519(13) 0.0005(10) 0.0038(11) -0.0116(11) 
C13 0.0715(17) 0.0620(14) 0.0491(13) -0.0006(11) 0.0070(11) 0.0088(12) 
C14 0.0457(13) 0.0809(17) 0.0717(16) 0.0046(13) 0.0053(11) -0.0007(12) 
C15 0.0473(13) 0.0607(14) 0.0634(14) 0.0020(11) 0.0071(10) -0.0096(11) 
C16 0.107(3) 0.0787(19) 0.087(2) 0.0104(16) -0.0001(18) 0.0232(18) 
 
_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 O2 1.4293(18) . ? 
S1 O3 1.4327(17) . ? 
S1 C10 1.758(2) . ? 
S1 C5 1.761(2) . ? 
O1 N1 1.264(2) . ? 
N1 C5 1.296(3) . ? 
N1 C2 1.523(3) . ? 
C5 C4 1.512(3) . ? 
C4 C9 1.523(4) . ? 
C4 C8 1.531(4) . ? 
C4 C3 1.548(4) . ? 
C3 C2 1.498(5) . ? 
C2 C6 1.495(4) . ? 
C2 C7 1.496(4) . ? 
C10 C11 1.385(3) . ? 
C10 C15 1.385(3) . ? 
C11 C12 1.376(3) . ? 
C12 C13 1.380(4) . ? 
C13 C14 1.394(3) . ? 
C13 C16 1.510(4) . ? 
C14 C15 1.370(3) . ? 
 
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 
O2 S1 O3 118.58(11) . . ? 
O2 S1 C10 109.23(10) . . ? 
O3 S1 C10 107.80(10) . . ? 
O2 S1 C5 109.02(11) . . ? 
O3 S1 C5 105.96(11) . . ? 
C10 S1 C5 105.47(9) . . ? 
O1 N1 C5 127.83(19) . . ? 
O1 N1 C2 119.36(19) . . ? 
C5 N1 C2 112.80(19) . . ? 
N1 C5 C4 114.3(2) . . ? 
N1 C5 S1 119.15(15) . . ? 
C4 C5 S1 126.49(17) . . ? 
C5 C4 C9 111.5(2) . . ? 
C5 C4 C8 111.7(2) . . ? 
C9 C4 C8 110.4(3) . . ? 
C5 C4 C3 99.9(2) . . ? 
C9 C4 C3 112.6(3) . . ? 
C8 C4 C3 110.5(3) . . ? 
C2 C3 C4 110.9(2) . . ? 
C6 C2 C7 113.0(4) . . ? 
C6 C2 C3 113.2(3) . . ? 
C7 C2 C3 113.5(4) . . ? 
C6 C2 N1 107.6(2) . . ? 
C7 C2 N1 107.0(2) . . ? 
C3 C2 N1 101.5(2) . . ? 
C11 C10 C15 120.5(2) . . ? 
C11 C10 S1 120.24(17) . . ? 
C15 C10 S1 119.16(16) . . ? 
C12 C11 C10 119.5(2) . . ? 
C11 C12 C13 121.2(2) . . ? 
C12 C13 C14 118.2(2) . . ? 
C12 C13 C16 121.3(3) . . ? 
C14 C13 C16 120.5(3) . . ? 
C15 C14 C13 121.6(2) . . ? 
C14 C15 C10 119.0(2) . . ? 
 
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 
C5 S1 C10 C15 87.74(18) . . . . ? 
O3 S1 C10 C15 -25.1(2) . . . . ? 
O2 S1 C10 C11 21.63(19) . . . . ? 
N1 C5 S1 C10 63.9(2) . . . . ? 
C4 C5 S1 C10 -115.1(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.989 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.989 
_refine_diff_density_max    0.202 
_refine_diff_density_min   -0.379 
_refine_diff_density_rms    0.063 
