# 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
'Frances Heaney'
'Desmond Cunningham'
'Julie Fenlon'
'Patrick McArdle'
;
Colm O'Mahony
;

_publ_contact_author_name        'Dr Frances Heaney'
_publ_contact_author_address     
;
Chemistry
National University of Ireland, Maynooth
Maynooth
Maynooth
Kildare
REPUBLIC OF IRELAND
;

_publ_contact_author_email       MARY.F.HEANEY@MAY.IE

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
a-Oximono-esters as precursors to heterocycles -
generation of oxazinone N-oxides and cycloaddition to alkene
dipolarophiles
;

data_fh1
_database_code_CSD               213558

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N O5 S'
_chemical_formula_weight         350.40

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   P21/c

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

_cell_length_a                   9.286(2)
_cell_length_b                   18.246(2)
_cell_length_c                   10.204(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.77(2)
_cell_angle_gamma                90.00
_cell_volume                     1728.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      18

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'scintillation counter'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4975
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.97
_reflns_number_total             4154
_reflns_number_gt                3062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_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)+(0.1501P)²+0.0000P] where P=(Fo²+2Fc²)/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         4154
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1956
_refine_ls_wR_factor_gt          0.1830
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_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 0.68186(5) 0.70531(3) 0.16744(5) 0.0455(2) Uani 1 1 d . . .
N1 N 1.04802(17) 0.77832(10) 0.11034(15) 0.0426(4) Uani 1 1 d . . .
O1 O 0.92612(14) 0.74091(7) 0.04720(12) 0.0416(3) Uani 1 1 d . . .
O2 O 1.1647(2) 0.85356(13) 0.32693(19) 0.0816(6) Uani 1 1 d . . .
O3 O 0.7571(2) 0.67704(11) 0.28143(14) 0.0644(5) Uani 1 1 d . . .
O4 O 0.54528(18) 0.74035(11) 0.1846(2) 0.0747(6) Uani 1 1 d . . .
O5 O 1.0403(3) 0.95216(13) 0.2783(3) 0.1010(8) Uani 1 1 d . . .
C2A C 0.9872(2) 0.85066(11) 0.1423(2) 0.0478(5) Uani 1 1 d . . .
C1 C 0.7945(2) 0.77259(10) 0.08883(18) 0.0397(4) Uani 1 1 d . . .
H1 H 0.7430 0.7928 0.0126 0.052 Uiso 1 1 calc R . .
C2 C 0.8317(2) 0.83441(11) 0.1834(2) 0.0479(5) Uani 1 1 d . . .
H2A H 0.8271 0.8185 0.2739 0.062 Uiso 1 1 calc R . .
H2B H 0.7693 0.8765 0.1703 0.062 Uiso 1 1 calc R . .
C3 C 1.0669(3) 0.88962(16) 0.2543(3) 0.0671(7) Uani 1 1 d . . .
C4 C 1.2088(3) 0.7813(2) 0.2929(3) 0.0741(8) Uani 1 1 d . . .
H4A H 1.2411 0.7561 0.3717 0.096 Uiso 1 1 calc R . .
H4B H 1.2899 0.7844 0.2343 0.096 Uiso 1 1 calc R . .
C5 C 1.0912(2) 0.73699(13) 0.2280(2) 0.0500(5) Uani 1 1 d . . .
H5 H 1.0094 0.7314 0.2869 0.065 Uiso 1 1 calc R . .
C6 C 0.6629(2) 0.63447(10) 0.05272(18) 0.0411(4) Uani 1 1 d . . .
C7 C 0.5543(2) 0.63898(13) -0.0409(2) 0.0534(5) Uani 1 1 d . . .
H7 H 0.4925 0.6791 -0.0431 0.069 Uiso 1 1 calc R . .
C8 C 0.5391(3) 0.58333(14) -0.1304(2) 0.0639(6) Uani 1 1 d . . .
H8 H 0.4663 0.5856 -0.1938 0.083 Uiso 1 1 calc R . .
C9 C 0.6306(3) 0.52434(14) -0.1271(2) 0.0653(7) Uani 1 1 d . . .
H9 H 0.6197 0.4870 -0.1885 0.085 Uiso 1 1 calc R . .
C10 C 0.7378(3) 0.51997(14) -0.0341(3) 0.0664(6) Uani 1 1 d . . .
H10 H 0.7990 0.4796 -0.0325 0.086 Uiso 1 1 calc R . .
C11 C 0.7557(2) 0.57517(12) 0.0575(2) 0.0540(5) Uani 1 1 d . . .
H11 H 0.8284 0.5725 0.1209 0.070 Uiso 1 1 calc R . .
C12 C 0.9888(3) 0.89881(14) 0.0209(3) 0.0653(6) Uani 1 1 d . . .
H12A H 0.9500 0.9461 0.0416 0.085 Uiso 1 1 calc R . .
H12B H 0.9313 0.8765 -0.0470 0.085 Uiso 1 1 calc R . .
H12C H 1.0859 0.9042 -0.0085 0.085 Uiso 1 1 calc R . .
C13 C 1.1481(3) 0.66236(17) 0.1875(3) 0.0721(7) Uani 1 1 d . . .
H13A H 1.1878 0.6377 0.2628 0.094 Uiso 1 1 calc R . .
H13B H 1.2217 0.6686 0.1232 0.094 Uiso 1 1 calc R . .
H13C H 1.0709 0.6337 0.1508 0.094 Uiso 1 1 calc R . .
C14 C 0.4696(5) 0.0669(3) 0.0498(3) 0.0995(13) Uani 1 1 d . . .
H14 H 0.4488 0.1130 0.0834 0.129 Uiso 1 1 calc R . .
C15 C 0.3831(4) 0.0108(3) 0.0768(3) 0.1029(14) Uani 1 1 d . . .
H15 H 0.3037 0.0183 0.1297 0.134 Uiso 1 1 calc R . .
C16 C 0.4092(4) -0.0579(3) 0.0280(3) 0.0994(11) Uani 1 1 d . . .
H16 H 0.3485 -0.0970 0.0460 0.129 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 O4 1.4331(18) . ?
S1 O3 1.4440(17) . ?
S1 C6 1.7512(19) . ?
S1 C1 1.8074(19) . ?
N1 O1 1.4639(19) . ?
N1 C5 1.469(3) . ?
N1 C2A 1.474(3) . ?
O1 C1 1.422(2) . ?
O2 C3 1.338(4) . ?
O2 C4 1.425(4) . ?
O5 C3 1.194(4) . ?
C2A C12 1.519(3) . ?
C2A C3 1.528(3) . ?
C2A C2 1.538(3) . ?
C1 C2 1.521(3) . ?
C4 C5 1.505(3) . ?
C5 C13 1.520(4) . ?
C6 C7 1.383(3) . ?
C6 C11 1.383(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.371(4) . ?
C9 C10 1.369(4) . ?
C10 C11 1.382(3) . ?
C14 C15 1.332(6) . ?
C14 C16 1.395(5) 3_655 ?
C15 C16 1.371(6) . ?
C16 C14 1.395(5) 3_655 ?

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
O4 S1 O3 118.71(12) . . ?
O4 S1 C6 109.26(10) . . ?
O3 S1 C6 108.53(10) . . ?
O4 S1 C1 105.64(11) . . ?
O3 S1 C1 108.87(9) . . ?
C6 S1 C1 104.96(9) . . ?
O1 N1 C5 108.74(15) . . ?
O1 N1 C2A 102.65(14) . . ?
C5 N1 C2A 112.33(16) . . ?
C1 O1 N1 109.97(13) . . ?
C3 O2 C4 121.03(19) . . ?
N1 C2A C12 109.24(18) . . ?
N1 C2A C3 113.53(19) . . ?
C12 C2A C3 109.33(19) . . ?
N1 C2A C2 104.56(15) . . ?
C12 C2A C2 110.65(19) . . ?
C3 C2A C2 109.45(17) . . ?
O1 C1 C2 107.60(14) . . ?
O1 C1 S1 111.18(13) . . ?
C2 C1 S1 110.48(14) . . ?
C1 C2 C2A 100.15(15) . . ?
O5 C3 O2 119.8(2) . . ?
O5 C3 C2A 119.9(3) . . ?
O2 C3 C2A 120.2(2) . . ?
O2 C4 C5 113.3(2) . . ?
N1 C5 C4 105.8(2) . . ?
N1 C5 C13 109.26(18) . . ?
C4 C5 C13 110.4(2) . . ?
C7 C6 C11 121.3(2) . . ?
C7 C6 S1 118.92(17) . . ?
C11 C6 S1 119.82(15) . . ?
C8 C7 C6 118.9(2) . . ?
C9 C8 C7 120.4(2) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C11 120.4(2) . . ?
C10 C11 C6 118.5(2) . . ?
C15 C14 C16 121.4(4) . 3_655 ?
C14 C15 C16 121.1(3) . . ?
C15 C16 C14 117.5(4) . 3_655 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.104

data_jf1
_database_code_CSD               213559

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N O5 S'
_chemical_formula_weight         325.37

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   P212121

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                   8.3850(10)
_cell_length_b                   11.2710(10)
_cell_length_c                   16.603(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1569.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      18

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Marresearch image plate'
_diffrn_measurement_method       '180 mm image plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6779
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         21.17
_reflns_number_total             1683
_reflns_number_gt                1641
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Marresearch MarControl software'
_computing_cell_refinement       'XDS (W.Kabsch, 2000)'
_computing_data_reduction        'XDS (W.Kabsch, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_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)+(0.0579P)²+0.4149P] where P=(Fo²+2Fc²)/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   -0.02(8)
_refine_ls_number_reflns         1683
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.859
_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 0.22893(7) 0.42943(5) 0.54172(3) 0.0346(2) Uani 1 1 d . . .
O1 O 0.13093(17) 0.38186(13) 0.69023(10) 0.0350(4) Uani 1 1 d . . .
O2 O 0.3597(2) 0.07251(16) 0.75564(10) 0.0479(5) Uani 1 1 d . . .
O3 O 0.2107(2) 0.31120(14) 0.51157(9) 0.0469(5) Uani 1 1 d . . .
O4 O 0.3490(2) 0.50510(15) 0.50738(10) 0.0492(5) Uani 1 1 d . . .
O5 O 0.5693(2) 0.17629(17) 0.78673(13) 0.0660(6) Uani 1 1 d . . .
N1 N 0.1731(2) 0.27582(15) 0.73660(11) 0.0325(5) Uani 1 1 d . . .
C2A C 0.3467(3) 0.29109(19) 0.74975(14) 0.0326(6) Uani 1 1 d . . .
C1 C 0.2685(3) 0.4250(2) 0.64853(12) 0.0315(5) Uani 1 1 d . . .
H1 H 0.2913 0.5058 0.6672 0.041 Uiso 1 1 calc R . .
C2 C 0.4078(3) 0.3459(2) 0.67052(14) 0.0338(6) Uani 1 1 d . . .
H2A H 0.5046 0.3913 0.6788 0.044 Uiso 1 1 calc R . .
H2B H 0.4265 0.2857 0.6298 0.044 Uiso 1 1 calc R . .
C3 C 0.4316(3) 0.1757(2) 0.76630(15) 0.0413(6) Uani 1 1 d . . .
C4 C 0.1887(3) 0.0645(2) 0.73694(15) 0.0385(6) Uani 1 1 d . . .
H4 H 0.1288 0.0626 0.7876 0.046 Uiso 1 1 calc R . .
C5 C 0.1336(3) 0.1698(2) 0.68822(15) 0.0353(6) Uani 1 1 d . . .
H5 H 0.1896 0.1723 0.6364 0.046 Uiso 1 1 calc R . .
C6 C 0.0424(3) 0.5010(2) 0.53716(14) 0.0324(6) Uani 1 1 d . . .
C7 C 0.0351(3) 0.6224(2) 0.54684(16) 0.0403(6) Uani 1 1 d . . .
H7 H 0.1278 0.6665 0.5540 0.052 Uiso 1 1 calc R . .
C8 C -0.1117(3) 0.6771(2) 0.54572(17) 0.0525(7) Uani 1 1 d . . .
H8 H -0.1185 0.7591 0.5513 0.068 Uiso 1 1 calc R . .
C9 C -0.2475(3) 0.6114(3) 0.53651(15) 0.0528(7) Uani 1 1 d . . .
H9 H -0.3463 0.6489 0.5366 0.069 Uiso 1 1 calc R . .
C10 C -0.2395(3) 0.4904(2) 0.52718(15) 0.0495(7) Uani 1 1 d . . .
H10 H -0.3326 0.4465 0.5209 0.064 Uiso 1 1 calc R . .
C11 C -0.0944(3) 0.4344(2) 0.52719(14) 0.0400(6) Uani 1 1 d . . .
H11 H -0.0881 0.3526 0.5206 0.052 Uiso 1 1 calc R . .
C12 C 0.3708(3) 0.3768(2) 0.82013(15) 0.0437(6) Uani 1 1 d . . .
H12A H 0.3231 0.4519 0.8073 0.061 Uiso 1 1 calc R . .
H12B H 0.4828 0.3874 0.8296 0.061 Uiso 1 1 calc R . .
H12C H 0.3215 0.3448 0.8676 0.061 Uiso 1 1 calc R . .
C13 C 0.1692(3) -0.0528(2) 0.69547(17) 0.0514(7) Uani 1 1 d . . .
H13A H 0.2256 -0.0515 0.6452 0.072 Uiso 1 1 calc R . .
H13B H 0.0580 -0.0672 0.6857 0.072 Uiso 1 1 calc R . .
H13C H 0.2115 -0.1146 0.7290 0.072 Uiso 1 1 calc R . .
C14 C -0.0447(3) 0.1653(3) 0.67489(18) 0.0531(7) Uani 1 1 d . . .
H14A H -0.0976 0.1531 0.7255 0.074 Uiso 1 1 calc R . .
H14B H -0.0699 0.1012 0.6390 0.074 Uiso 1 1 calc R . .
H14C H -0.0798 0.2389 0.6517 0.074 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 O3 1.4316(17) . ?
S1 O4 1.4375(18) . ?
S1 C6 1.762(2) . ?
S1 C1 1.805(2) . ?
O1 C1 1.431(3) . ?
O1 N1 1.465(2) . ?
O2 C3 1.322(3) . ?
O2 C4 1.470(3) . ?
O5 C3 1.204(3) . ?
N1 C5 1.478(3) . ?
N1 C2A 1.482(3) . ?
C2A C3 1.508(4) . ?
C2A C12 1.529(4) . ?
C2A C2 1.541(3) . ?
C1 C2 1.514(3) . ?
C4 C13 1.499(4) . ?
C4 C5 1.509(3) . ?
C5 C14 1.512(3) . ?
C6 C7 1.378(3) . ?
C6 C11 1.381(3) . ?
C7 C8 1.378(4) . ?
C8 C9 1.367(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.371(4) . ?

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
O3 S1 O4 119.24(11) . . ?
O3 S1 C6 108.45(11) . . ?
O4 S1 C6 109.45(11) . . ?
O3 S1 C1 109.74(10) . . ?
O4 S1 C1 106.09(10) . . ?
C6 S1 C1 102.59(10) . . ?
C1 O1 N1 109.71(15) . . ?
C3 O2 C4 121.8(2) . . ?
O1 N1 C5 108.68(16) . . ?
O1 N1 C2A 102.70(15) . . ?
C5 N1 C2A 113.21(18) . . ?
N1 C2A C3 112.97(19) . . ?
N1 C2A C12 108.37(19) . . ?
C3 C2A C12 110.1(2) . . ?
N1 C2A C2 104.30(18) . . ?
C3 C2A C2 110.2(2) . . ?
C12 C2A C2 110.82(18) . . ?
O1 C1 C2 107.73(16) . . ?
O1 C1 S1 109.67(14) . . ?
C2 C1 S1 113.24(15) . . ?
C1 C2 C2A 100.71(17) . . ?
O5 C3 O2 118.7(2) . . ?
O5 C3 C2A 120.0(2) . . ?
O2 C3 C2A 121.3(2) . . ?
O2 C4 C13 104.9(2) . . ?
O2 C4 C5 111.3(2) . . ?
C13 C4 C5 114.4(2) . . ?
N1 C5 C4 106.04(18) . . ?
N1 C5 C14 109.1(2) . . ?
C4 C5 C14 110.8(2) . . ?
C7 C6 C11 121.1(2) . . ?
C7 C6 S1 119.26(19) . . ?
C11 C6 S1 119.55(17) . . ?
C8 C7 C6 118.8(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C10 C11 C6 119.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        21.17
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.077



