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


data_global

#------------------ AUDIT DETAILS-------------------------------------------#

_audit_creation_date             2002-11-05
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#------------------ SUBMISSION DETAILS --------------------------------------#

_journal_coden_Cambridge         177

_publ_contact_letter             # Include date of submission
;
Date of submission 06.27.2003

Please consider this CIF submission for supplement to our
publication in O.B.C..
;

_publ_section_title              
;
C-Glycosylmethylene Carbenes: Synthesis of Anhydro-aldose Tosylhydrazones as
Precursors, Generation, and a New Route to exo-Glycals
;

_publ_section_title_footnote     
;
?
;

loop_
_publ_author_name
_publ_author_address
'Toth, Marietta'
;
Department of Organic Chemistry
University of Debrecen
Debrecen, H-4010
Hungary
;
'Kover,E. Katalin'
;
Department of Inorganic and Analytical Chemistry
University of Debrecen
Debrecen, H-4010
Hungary
;
'Benyei, Attila C.'
;
Department of Physical Chemistry
University of Debrecen
Debrecen, H-4010
Hungary
;
'Somsak, Laszlo'
;
Department of Organic Chemistry
University of Debrecen
Debrecen, H-4010
Hungary
;

_publ_contact_author_name        'Prof Laszlo Somsak'
_publ_contact_author_address     
;
Department of Organic Chemistry
University of Debrecen
Egyetem ter 1. POB 20
Debrecen
H-4010
HUNGARY
;

_publ_contact_author_email       SOMSAK@TIGRIS.KLTE.HU

_publ_section_references         
;

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
(1993) J. Appl. Cryst. 26, 343-350.

Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G.
& Spagna, R. (1999) J. Appl. Cryst. 32, 115-119.

Enraf-Nonius (1996). MACH3/PC Software. Enraf-Nonius, Delft,
The Netherlands.

Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
Laboratory, Tennessee, USA.

Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
& Taylor, R. (1992). International Tables for Crystallography,
Volume C.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Spek, A.L. (1990). Acta Cryst. A46, C34

Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr.
34, 824-828

Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr.
35, 281.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
A.C.B. is indebted for the Hungarian Academy of Sciences for
a Bolyai Postdoctoral Fellowship.
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (Å²)

Table 2. Selected geometric parameters (Å ,° )
;

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_0044b
_database_code_CSD               213880

_audit_creation_date             2002-11-05T10:01:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C19 H24 N2 O9 S1'
_chemical_formula_sum            'C19 H24 N2 O9 S'
_chemical_formula_weight         456.46
_chemical_melting_point          83

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           orthorhombic
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.939(7)
_cell_length_b                   12.907(5)
_cell_length_c                   20.160(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2586(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.75
_cell_measurement_theta_max      13.89

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.17
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.8686
_exptl_absorpt_correction_T_max  0.9295

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_refln_scan_mode          ot
_diffrn_refln_scan_width         2.64
_diffrn_refln_scan_mode_backgd   mo
_diffrn_standards_number         4
_diffrn_standards_interval_count 39
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        38
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -7 4
-3 -2 7
3 -1 8
-4 0 9

_diffrn_reflns_number            5867
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total             5867
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'MACH3/PC (Enraf Nonius, 1996)'
_computing_cell_refinement       'MACH3/PC (Enraf Nonius, 1996)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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)+(0.0991P)²+0.0233P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5867
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1828
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.196

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.2367(7) 0.1079(6) 0.7504(4) 0.0753(18) Uani 1 d . . .
C2 C 0.3229(5) 0.1897(5) 0.7787(3) 0.0728(18) Uani 1 d . . .
H2 H 0.3012 0.2567 0.7584 0.087 Uiso 1 calc R . .
C3 C 0.4762(5) 0.1643(5) 0.7686(3) 0.0656(15) Uani 1 d . . .
H3 H 0.4946 0.0945 0.7855 0.079 Uiso 1 calc R . .
C4 C 0.5593(5) 0.2398(5) 0.8054(3) 0.0650(16) Uani 1 d . . .
H4 H 0.5518 0.3081 0.7845 0.078 Uiso 1 calc R . .
C5 C 0.5207(6) 0.2476(5) 0.8761(3) 0.0772(17) Uani 1 d . . .
H5 H 0.5719 0.3028 0.8978 0.093 Uiso 1 calc R . .
C6 C 0.3701(7) 0.2679(5) 0.8828(3) 0.093(2) Uani 1 d . . .
H6A H 0.3452 0.266 0.9293 0.111 Uiso 1 calc R . .
H6B H 0.3494 0.3363 0.8658 0.111 Uiso 1 calc R . .
C7 C 0.5304(7) 0.0789(8) 0.6670(4) 0.094(2) Uani 1 d . . .
C8 C 0.5628(8) 0.0980(7) 0.5983(3) 0.123(3) Uani 1 d . . .
H8A H 0.5621 0.1712 0.59 0.184 Uiso 1 calc R . .
H8B H 0.4975 0.0647 0.5705 0.184 Uiso 1 calc R . .
H8C H 0.6506 0.0707 0.5888 0.184 Uiso 1 calc R . .
C9 C 0.7925(7) 0.2723(8) 0.7992(3) 0.090(2) Uani 1 d . . .
C10 C 0.9317(7) 0.2267(6) 0.7993(4) 0.121(3) Uani 1 d . . .
H10A H 0.9257 0.1524 0.7992 0.182 Uiso 1 calc R . .
H10B H 0.9789 0.249 0.8383 0.182 Uiso 1 calc R . .
H10C H 0.9794 0.2494 0.7606 0.182 Uiso 1 calc R . .
C11 C 0.6630(11) 0.1418(9) 0.9378(4) 0.113(3) Uani 1 d . . .
C12 C 0.6900(9) 0.0305(9) 0.9542(4) 0.160(4) Uani 1 d . . .
H12A H 0.6132 -0.0107 0.9424 0.24 Uiso 1 calc R . .
H12B H 0.7069 0.0238 1.0009 0.24 Uiso 1 calc R . .
H12C H 0.7671 0.0069 0.9298 0.24 Uiso 1 calc R . .
C13 C 0.1224(7) 0.0603(8) 0.5527(3) 0.095(2) Uani 1 d . . .
C14 C 0.1645(9) 0.1529(8) 0.5280(5) 0.123(3) Uani 1 d . . .
H14 H 0.1265 0.214 0.5438 0.148 Uiso 1 calc . . .
C15 C 0.2608(11) 0.1573(7) 0.4808(5) 0.130(3) Uani 1 d . . .
H15 H 0.2916 0.2218 0.467 0.156 Uiso 1 calc . . .
C16 C 0.3156(9) 0.0688(10) 0.4521(4) 0.115(2) Uani 1 d . . .
C17 C 0.2760(11) -0.0275(7) 0.4801(5) 0.122(3) Uani 1 d . . .
H17 H 0.3158 -0.0888 0.4659 0.147 Uiso 1 calc . . .
C18 C 0.1781(10) -0.0296(7) 0.5286(5) 0.114(3) Uani 1 d . . .
H18 H 0.1492 -0.0929 0.5453 0.136 Uiso 1 calc . . .
C19 C 0.4202(10) 0.0749(8) 0.3984(5) 0.154(3) Uani 1 d . . .
H19A H 0.4364 0.1462 0.3873 0.231 Uiso 1 calc R . .
H19B H 0.3888 0.0387 0.3598 0.231 Uiso 1 calc R . .
H19C H 0.5022 0.0438 0.4137 0.231 Uiso 1 calc R . .
N1 N 0.1597(6) 0.1264(4) 0.7033(3) 0.0848(16) Uani 1 d . . .
N2 N 0.0760(6) 0.0458(6) 0.6838(3) 0.093(2) Uani 1 d . . .
O1 O 0.2937(4) 0.1921(3) 0.8472(2) 0.0809(12) Uani 1 d . . .
O2 O 0.5056(4) 0.1675(3) 0.7005(2) 0.0736(10) Uani 1 d . . .
O3 O 0.5274(7) -0.0028(5) 0.6940(3) 0.133(2) Uani 1 d . . .
O4 O 0.6963(4) 0.2032(3) 0.8002(2) 0.0788(12) Uani 1 d . . .
O5 O 0.7720(5) 0.3641(4) 0.7983(3) 0.1196(19) Uani 1 d . . .
O6 O 0.5462(5) 0.1508(4) 0.9075(2) 0.0886(14) Uani 1 d . . .
O7 O 0.7377(7) 0.2111(6) 0.9505(3) 0.148(3) Uani 1 d . . .
O8 O -0.0715(5) 0.1525(5) 0.6140(3) 0.139(2) Uani 1 d . . .
O9 O -0.0722(5) -0.0426(4) 0.6068(3) 0.137(2) Uani 1 d . . .
S1 S -0.0015(2) 0.05454(18) 0.61358(10) 0.1065(7) Uani 1 d . . .
H1 H 0.248(5) 0.032(4) 0.777(2) 0.068(16) Uiso 1 d . . .
H2N H 0.095(4) -0.003(3) 0.698(2) 0.012(13) Uiso 1 d . . .


#------------------ 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_2
_geom_bond_publ_flag
C1 N1 1.243(7) . ?
C1 C2 1.474(8) . ?
C2 O1 1.412(6) . ?
C2 C3 1.572(8) . ?
C3 O2 1.404(6) . ?
C3 C4 1.478(7) . ?
C4 O4 1.446(6) . ?
C4 C5 1.478(7) . ?
C5 O6 1.424(7) . ?
C5 C6 1.525(9) . ?
C6 O1 1.431(7) . ?
C7 O3 1.188(8) . ?
C7 O2 1.351(8) . ?
C7 C8 1.442(9) . ?
C9 O5 1.202(8) . ?
C9 O4 1.308(8) . ?
C9 C10 1.504(9) . ?
C11 O7 1.189(10) . ?
C11 O6 1.317(10) . ?
C11 C12 1.499(12) . ?
C13 C14 1.361(10) . ?
C13 C18 1.374(10) . ?
C13 S1 1.741(8) . ?
C14 C15 1.350(12) . ?
C15 C16 1.392(12) . ?
C16 C17 1.421(11) . ?
C16 C19 1.503(11) . ?
C17 C18 1.379(12) . ?
N1 N2 1.390(7) . ?
N2 S1 1.615(6) . ?
O8 S1 1.443(5) . ?
O9 S1 1.444(5) . ?

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
N1 C1 C2 120.9(7) . . ?
O1 C2 C1 105.9(5) . . ?
O1 C2 C3 109.2(5) . . ?
C1 C2 C3 111.3(5) . . ?
O2 C3 C4 110.8(5) . . ?
O2 C3 C2 108.7(5) . . ?
C4 C3 C2 109.8(5) . . ?
O4 C4 C5 109.7(5) . . ?
O4 C4 C3 105.9(4) . . ?
C5 C4 C3 112.6(5) . . ?
O6 C5 C4 108.9(5) . . ?
O6 C5 C6 106.6(5) . . ?
C4 C5 C6 110.6(5) . . ?
O1 C6 C5 111.0(5) . . ?
O3 C7 O2 121.2(7) . . ?
O3 C7 C8 126.6(9) . . ?
O2 C7 C8 112.2(8) . . ?
O5 C9 O4 123.3(6) . . ?
O5 C9 C10 122.8(7) . . ?
O4 C9 C10 113.9(7) . . ?
O7 C11 O6 125.7(10) . . ?
O7 C11 C12 124.1(10) . . ?
O6 C11 C12 110.1(10) . . ?
C14 C13 C18 119.2(8) . . ?
C14 C13 S1 120.9(8) . . ?
C18 C13 S1 119.9(8) . . ?
C15 C14 C13 120.8(9) . . ?
C14 C15 C16 122.4(9) . . ?
C15 C16 C17 116.3(8) . . ?
C15 C16 C19 121.8(10) . . ?
C17 C16 C19 121.6(11) . . ?
C18 C17 C16 119.6(9) . . ?
C13 C18 C17 121.2(8) . . ?
C1 N1 N2 116.2(6) . . ?
N1 N2 S1 118.8(6) . . ?
C2 O1 C6 113.4(5) . . ?
C7 O2 C3 120.2(5) . . ?
C9 O4 C4 117.8(5) . . ?
C11 O6 C5 116.2(7) . . ?
O8 S1 O9 121.8(3) . . ?
O8 S1 N2 106.6(4) . . ?
O9 S1 N2 104.8(4) . . ?
O8 S1 C13 107.9(4) . . ?
O9 S1 C13 108.4(4) . . ?
N2 S1 C13 106.5(3) . . ?

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
N2 H2N O5 0.72(4) 2.17(4) 2.813(9) 150(4) 4_646


