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#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_ad1
_database_code_depnum_ccdc_archive 'CCDC 267826'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O4 S'
_chemical_formula_weight         308.35

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   P2(1)2(1)2(1)

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                   7.7121(7)
_cell_length_b                   10.7290(9)
_cell_length_c                   17.409(1)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1440.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1018
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      28.22

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9265
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15178
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3572
_reflns_number_gt                3520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0453P)^2^+0.2095P] 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    refall
_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   -0.05(4)
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.47291(3) 0.43538(2) 0.202768(15) 0.01530(7) Uani 1 1 d . . .
O1 O 0.42175(11) 0.49725(8) 0.27226(5) 0.01969(17) Uani 1 1 d . . .
O2 O 0.37405(11) 0.33152(8) 0.17490(5) 0.02101(18) Uani 1 1 d . . .
O3 O 0.50643(14) 0.93484(9) -0.02260(6) 0.0320(2) Uani 1 1 d . . .
O4 O 0.43025(15) 0.79646(10) -0.10683(5) 0.0336(2) Uani 1 1 d . . .
N1 N 0.66937(12) 0.38875(9) 0.21287(6) 0.01668(18) Uani 1 1 d . . .
N2 N 0.46924(15) 0.82814(10) -0.04119(6) 0.0231(2) Uani 1 1 d . . .
C1 C 0.80341(15) 0.46806(11) 0.25079(7) 0.0182(2) Uani 1 1 d . . .
C2 C 0.97149(16) 0.41465(13) 0.21691(7) 0.0247(2) Uani 1 1 d . . .
C3 C 0.92784(16) 0.27733(12) 0.20285(8) 0.0258(2) Uani 1 1 d . . .
C4 C 0.74332(16) 0.28033(11) 0.16962(7) 0.0196(2) Uani 1 1 d . . .
C5 C 0.79810(15) 0.45464(11) 0.33664(7) 0.0197(2) Uani 1 1 d . . .
C6 C 0.75653(17) 0.54546(12) 0.38435(7) 0.0239(2) Uani 1 1 d . . .
C7 C 0.74185(15) 0.29815(11) 0.08417(7) 0.0208(2) Uani 1 1 d . . .
C8 C 0.66180(18) 0.22095(13) 0.03688(8) 0.0272(3) Uani 1 1 d . . .
C11 C 0.47114(14) 0.55169(10) 0.13026(6) 0.01591(19) Uani 1 1 d . . .
C12 C 0.51489(16) 0.67379(11) 0.14953(6) 0.0189(2) Uani 1 1 d . . .
C13 C 0.51612(16) 0.76543(10) 0.09297(7) 0.0200(2) Uani 1 1 d . . .
C14 C 0.47055(16) 0.73086(11) 0.01892(6) 0.0197(2) Uani 1 1 d . . .
C15 C 0.42470(16) 0.61034(11) -0.00118(7) 0.0211(2) Uani 1 1 d . . .
C16 C 0.42563(15) 0.51939(11) 0.05537(7) 0.0198(2) Uani 1 1 d . . .
H1 H 0.785(2) 0.5552(14) 0.2377(9) 0.020(4) Uiso 1 1 d . . .
H4 H 0.6786(19) 0.2072(14) 0.1816(8) 0.014(3) Uiso 1 1 d . . .
H5 H 0.826(2) 0.3777(15) 0.3545(9) 0.022(4) Uiso 1 1 d . . .
H7 H 0.802(2) 0.3659(17) 0.0630(11) 0.035(5) Uiso 1 1 d . . .
H12 H 0.550(2) 0.6944(15) 0.2004(9) 0.025(4) Uiso 1 1 d . . .
H13 H 0.545(2) 0.8463(15) 0.1048(9) 0.022(4) Uiso 1 1 d . . .
H15 H 0.389(2) 0.5917(15) -0.0533(9) 0.023(4) Uiso 1 1 d . . .
H16 H 0.396(2) 0.4395(16) 0.0434(9) 0.025(4) Uiso 1 1 d . . .
H2A H 1.004(2) 0.4568(16) 0.1679(10) 0.028(4) Uiso 1 1 d . . .
H3A H 1.005(2) 0.2382(18) 0.1682(11) 0.036(5) Uiso 1 1 d . . .
H6A H 0.761(2) 0.5317(16) 0.4387(11) 0.033(4) Uiso 1 1 d . . .
H8A H 0.597(3) 0.1556(19) 0.0567(11) 0.044(5) Uiso 1 1 d . . .
H2B H 1.068(2) 0.4294(15) 0.2516(9) 0.019(3) Uiso 1 1 d . . .
H3B H 0.925(2) 0.2314(16) 0.2499(10) 0.028(4) Uiso 1 1 d . . .
H6B H 0.721(2) 0.6251(16) 0.3671(9) 0.024(4) Uiso 1 1 d . . .
H8B H 0.667(2) 0.2305(15) -0.0166(10) 0.029(4) Uiso 1 1 d . . .

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 0.01435(12) 0.01384(11) 0.01771(12) 0.00010(9) 0.00146(9) 0.00090(9)
O1 0.0187(4) 0.0205(4) 0.0199(4) -0.0013(3) 0.0036(3) 0.0038(3)
O2 0.0184(4) 0.0172(4) 0.0274(4) -0.0005(3) 0.0010(3) -0.0024(3)
O3 0.0453(6) 0.0199(4) 0.0309(5) 0.0059(3) 0.0032(4) 0.0017(4)
O4 0.0459(6) 0.0332(5) 0.0216(4) 0.0062(4) -0.0017(4) 0.0069(4)
N1 0.0147(4) 0.0157(4) 0.0197(5) -0.0016(3) 0.0003(4) 0.0017(3)
N2 0.0238(5) 0.0227(5) 0.0228(5) 0.0044(4) 0.0036(4) 0.0074(4)
C1 0.0161(5) 0.0185(5) 0.0199(5) 0.0026(4) -0.0007(4) -0.0004(4)
C2 0.0160(5) 0.0342(6) 0.0238(5) 0.0030(5) 0.0013(5) 0.0028(5)
C3 0.0243(6) 0.0290(6) 0.0241(5) 0.0016(5) 0.0024(5) 0.0121(5)
C4 0.0220(5) 0.0155(5) 0.0212(5) 0.0010(4) 0.0042(4) 0.0048(4)
C5 0.0190(5) 0.0195(5) 0.0205(5) 0.0023(4) -0.0012(4) -0.0006(4)
C6 0.0232(6) 0.0242(6) 0.0243(6) -0.0007(4) -0.0007(5) -0.0019(5)
C7 0.0224(5) 0.0185(5) 0.0215(5) 0.0014(4) 0.0046(4) 0.0041(4)
C8 0.0298(6) 0.0250(6) 0.0266(6) -0.0039(5) 0.0024(5) 0.0022(5)
C11 0.0145(4) 0.0155(5) 0.0178(5) 0.0012(4) 0.0005(4) 0.0035(4)
C12 0.0214(5) 0.0164(5) 0.0188(5) -0.0013(4) -0.0004(4) 0.0030(4)
C13 0.0222(5) 0.0150(5) 0.0226(5) 0.0003(4) 0.0006(4) 0.0020(4)
C14 0.0202(5) 0.0192(5) 0.0196(5) 0.0037(4) 0.0022(4) 0.0050(4)
C15 0.0227(5) 0.0211(5) 0.0196(5) -0.0002(4) -0.0021(4) 0.0043(4)
C16 0.0214(5) 0.0172(5) 0.0208(5) -0.0018(4) -0.0021(4) 0.0013(4)

_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 1.4346(9) . ?
S1 O1 1.4353(8) . ?
S1 N1 1.6052(10) . ?
S1 C11 1.7751(11) . ?
O3 N2 1.2238(14) . ?
O4 N2 1.2294(15) . ?
N1 C1 1.4928(15) . ?
N1 C4 1.4984(14) . ?
N2 C14 1.4780(14) . ?
C1 C5 1.5021(15) . ?
C1 C2 1.5351(16) . ?
C1 H1 0.972(15) . ?
C2 C3 1.5310(19) . ?
C2 H2A 0.996(17) . ?
C2 H2B 0.974(16) . ?
C3 C4 1.5365(17) . ?
C3 H3A 0.947(19) . ?
C3 H3B 0.956(17) . ?
C4 C7 1.4999(16) . ?
C4 H4 0.953(15) . ?
C5 C6 1.3198(17) . ?
C5 H5 0.907(16) . ?
C6 H6A 0.958(18) . ?
C6 H6B 0.946(17) . ?
C7 C8 1.3210(18) . ?
C7 H7 0.940(19) . ?
C8 H8A 0.93(2) . ?
C8 H8B 0.937(17) . ?
C11 C12 1.3937(15) . ?
C11 C16 1.3940(15) . ?
C12 C13 1.3915(15) . ?
C12 H12 0.952(16) . ?
C13 C14 1.3868(16) . ?
C13 H13 0.918(16) . ?
C14 C15 1.3855(17) . ?
C15 C16 1.3860(16) . ?
C15 H15 0.969(15) . ?
C16 H16 0.912(17) . ?

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 O1 119.88(5) . . ?
O2 S1 N1 107.25(5) . . ?
O1 S1 N1 108.14(5) . . ?
O2 S1 C11 107.55(5) . . ?
O1 S1 C11 105.79(5) . . ?
N1 S1 C11 107.71(5) . . ?
C1 N1 C4 113.65(9) . . ?
C1 N1 S1 121.63(7) . . ?
C4 N1 S1 123.10(8) . . ?
O3 N2 O4 124.18(10) . . ?
O3 N2 C14 118.15(10) . . ?
O4 N2 C14 117.68(11) . . ?
N1 C1 C5 111.50(9) . . ?
N1 C1 C2 101.66(9) . . ?
C5 C1 C2 111.69(10) . . ?
N1 C1 H1 110.1(9) . . ?
C5 C1 H1 108.8(9) . . ?
C2 C1 H1 113.0(9) . . ?
C3 C2 C1 103.59(10) . . ?
C3 C2 H2A 110.8(10) . . ?
C1 C2 H2A 111.6(10) . . ?
C3 C2 H2B 115.1(9) . . ?
C1 C2 H2B 110.4(9) . . ?
H2A C2 H2B 105.5(13) . . ?
C2 C3 C4 104.10(10) . . ?
C2 C3 H3A 112.9(12) . . ?
C4 C3 H3A 110.7(11) . . ?
C2 C3 H3B 111.3(10) . . ?
C4 C3 H3B 108.1(11) . . ?
H3A C3 H3B 109.4(15) . . ?
N1 C4 C7 113.36(9) . . ?
N1 C4 C3 100.35(9) . . ?
C7 C4 C3 112.52(10) . . ?
N1 C4 H4 109.3(9) . . ?
C7 C4 H4 108.5(9) . . ?
C3 C4 H4 112.7(9) . . ?
C6 C5 C1 124.20(11) . . ?
C6 C5 H5 120.9(10) . . ?
C1 C5 H5 114.9(10) . . ?
C5 C6 H6A 119.9(11) . . ?
C5 C6 H6B 122.4(10) . . ?
H6A C6 H6B 117.6(15) . . ?
C8 C7 C4 122.81(12) . . ?
C8 C7 H7 118.2(11) . . ?
C4 C7 H7 119.0(11) . . ?
C7 C8 H8A 119.6(12) . . ?
C7 C8 H8B 122.1(11) . . ?
H8A C8 H8B 118.3(16) . . ?
C12 C11 C16 121.32(10) . . ?
C12 C11 S1 119.19(8) . . ?
C16 C11 S1 119.49(8) . . ?
C13 C12 C11 119.70(10) . . ?
C13 C12 H12 119.5(9) . . ?
C11 C12 H12 120.7(9) . . ?
C14 C13 C12 117.85(10) . . ?
C14 C13 H13 121.4(10) . . ?
C12 C13 H13 120.7(10) . . ?
C15 C14 C13 123.30(10) . . ?
C15 C14 N2 118.59(10) . . ?
C13 C14 N2 118.11(10) . . ?
C14 C15 C16 118.45(11) . . ?
C14 C15 H15 120.1(9) . . ?
C16 C15 H15 121.4(9) . . ?
C15 C16 C11 119.38(11) . . ?
C15 C16 H16 119.9(10) . . ?
C11 C16 H16 120.8(10) . . ?

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
O2 S1 N1 C1 -171.74(8) . . . . ?
O1 S1 N1 C1 -41.15(10) . . . . ?
C11 S1 N1 C1 72.75(10) . . . . ?
O2 S1 N1 C4 23.69(10) . . . . ?
O1 S1 N1 C4 154.28(9) . . . . ?
C11 S1 N1 C4 -91.81(9) . . . . ?
C4 N1 C1 C5 -109.82(11) . . . . ?
S1 N1 C1 C5 84.27(11) . . . . ?
C4 N1 C1 C2 9.32(12) . . . . ?
S1 N1 C1 C2 -156.60(8) . . . . ?
N1 C1 C2 C3 -30.65(11) . . . . ?
C5 C1 C2 C3 88.35(11) . . . . ?
C1 C2 C3 C4 41.82(12) . . . . ?
C1 N1 C4 C7 -104.61(12) . . . . ?
S1 N1 C4 C7 61.07(13) . . . . ?
C1 N1 C4 C3 15.59(12) . . . . ?
S1 N1 C4 C3 -178.73(8) . . . . ?
C2 C3 C4 N1 -34.37(11) . . . . ?
C2 C3 C4 C7 86.43(12) . . . . ?
N1 C1 C5 C6 -114.97(13) . . . . ?
C2 C1 C5 C6 132.05(13) . . . . ?
N1 C4 C7 C8 -121.85(13) . . . . ?
C3 C4 C7 C8 125.14(13) . . . . ?
O2 S1 C11 C12 162.31(9) . . . . ?
O1 S1 C11 C12 33.09(10) . . . . ?
N1 S1 C11 C12 -82.37(10) . . . . ?
O2 S1 C11 C16 -17.49(10) . . . . ?
O1 S1 C11 C16 -146.71(9) . . . . ?
N1 S1 C11 C16 97.82(10) . . . . ?
C16 C11 C12 C13 -1.03(17) . . . . ?
S1 C11 C12 C13 179.17(9) . . . . ?
C11 C12 C13 C14 0.92(17) . . . . ?
C12 C13 C14 C15 -0.16(18) . . . . ?
C12 C13 C14 N2 179.16(11) . . . . ?
O3 N2 C14 C15 178.51(11) . . . . ?
O4 N2 C14 C15 -1.31(17) . . . . ?
O3 N2 C14 C13 -0.84(17) . . . . ?
O4 N2 C14 C13 179.34(12) . . . . ?
C13 C14 C15 C16 -0.52(19) . . . . ?
N2 C14 C15 C16 -179.83(11) . . . . ?
C14 C15 C16 C11 0.42(18) . . . . ?
C12 C11 C16 C15 0.34(17) . . . . ?
S1 C11 C16 C15 -179.86(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043