 
data_ab08 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C13 H17 N O4 S' 
_chemical_formula_weight          283.34 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'   0.3331   0.5567 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/a 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z' 
 
_cell_length_a                    8.367(4) 
_cell_length_b                    19.764(8) 
_cell_length_c                    8.672(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.16(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1428.2(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     290(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       15 
_cell_measurement_theta_max       20 
 
_exptl_crystal_description        Block 
_exptl_crystal_colour             Transparent 
_exptl_crystal_size_max           0.38 
_exptl_crystal_size_mid           0.35 
_exptl_crystal_size_min           0.19 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.318 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              600 
_exptl_absorpt_coefficient_mu     2.111 
_exptl_absorpt_correction_type    None 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       290(2) 
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Siemens R3m' 
_diffrn_measurement_method        '\w/2\q scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             2255 
_diffrn_reflns_av_R_equivalents   0.0181 
_diffrn_reflns_av_sigmaI/netI     0.0155 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -21 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          4.47 
_diffrn_reflns_theta_max          57.33 
_reflns_number_total              1959 
_reflns_number_observed           1809 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'Siemens control software' 
_computing_cell_refinement        'Siemens control software' 
_computing_data_reduction         'Siemens XDISK' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'SHELXTL-PLUS (Sheldrick 1990)' 
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)' 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses 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 observed criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+0.4093P] 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     'Riding atom' 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0065(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          1959 
_refine_ls_number_parameters      187 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0477 
_refine_ls_R_factor_obs           0.0459 
_refine_ls_wR_factor_all          0.1310 
_refine_ls_wR_factor_obs          0.1284 
_refine_ls_goodness_of_fit_all    1.028 
_refine_ls_goodness_of_fit_obs    1.053 
_refine_ls_restrained_S_all       1.028 
_refine_ls_restrained_S_obs       1.053 
_refine_ls_shift/esd_max          -0.044 
_refine_ls_shift/esd_mean         0.003 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
N1 N 0.0887(2) 0.55103(9) 0.6991(2) 0.0399(5) Uani 1 d . . 
H1 H 0.1327(2) 0.59208(9) 0.6504(2) 0.067(8) Uiso 1 calc R . 
C1 C 0.1758(2) 0.50783(10) 0.8008(2) 0.0395(5) Uani 1 d . . 
C2 C 0.0699(2) 0.45693(10) 0.8417(2) 0.0391(5) Uani 1 d . . 
C3 C -0.0796(2) 0.47079(10) 0.7631(2) 0.0403(5) Uani 1 d . . 
C4 C -0.0643(2) 0.52925(11) 0.6758(2) 0.0410(5) Uani 1 d . . 
C5 C -0.1856(3) 0.56737(14) 0.5730(3) 0.0559(7) Uani 1 d G . 
H5A H -0.2736(21) 0.5384(12) 0.5380(30) 0.109(4) Uiso 1 calc G . 
H5B H -0.1353(32) 0.5841(12) 0.4854(20) 0.109(4) Uiso 1 calc G . 
H5C H -0.2248(29) 0.6047(8) 0.6295(29) 0.109(4) Uiso 1 calc G . 
C6 C 0.3390(3) 0.51662(11) 0.8475(3) 0.0457(6) Uani 1 d . . 
H6 H 0.3858(3) 0.48408(11) 0.9146(3) 0.053(6) Uiso 1 calc R . 
S1 S 0.45771(7) 0.57750(3) 0.79792(8) 0.0645(3) Uani 1 d . . 
C7 C 0.1175(3) 0.39801(11) 0.9449(2) 0.0452(5) Uani 1 d . . 
H7A H 0.0232(3) 0.38018(11) 0.9882(2) 0.071(3) Uiso 1 calc R . 
H7B H 0.1922(3) 0.41320(11) 1.0299(2) 0.071(3) Uiso 1 calc R . 
C8 C 0.1948(3) 0.34263(12) 0.8571(3) 0.0580(7) Uani 1 d . . 
H8A H 0.1150(3) 0.32570(12) 0.7785(3) 0.071(3) Uiso 1 calc R . 
H8B H 0.2797(3) 0.36298(12) 0.8037(3) 0.071(3) Uiso 1 calc R . 
C9 C 0.2642(3) 0.28342(11) 0.9464(3) 0.0520(6) Uani 1 d . . 
O1 O 0.3296(3) 0.23730(11) 0.8878(2) 0.0894(7) Uani 1 d . . 
O2 O 0.2480(2) 0.28692(8) 1.0975(2) 0.0579(5) Uani 1 d . . 
C10 C 0.3162(4) 0.2312(2) 1.1894(4) 0.0749(8) Uani 1 d G . 
H10A H 0.3017(31) 0.2376(14) 1.2969(10) 0.109(4) Uiso 1 calc G . 
H10B H 0.4288(8) 0.2298(14) 1.1759(30) 0.109(4) Uiso 1 calc G . 
H10C H 0.2671(29) 0.1894(8) 1.1543(29) 0.109(4) Uiso 1 calc G . 
C11 C -0.2321(3) 0.43171(11) 0.7738(3) 0.0495(6) Uani 1 d . . 
H11A H -0.2276(3) 0.41015(11) 0.8746(3) 0.071(3) Uiso 1 calc R . 
H11B H -0.3211(3) 0.46333(11) 0.7675(3) 0.071(3) Uiso 1 calc R . 
C12 C -0.2658(2) 0.37848(11) 0.6517(2) 0.0428(5) Uani 1 d . . 
O3 O -0.1771(2) 0.35978(8) 0.5591(2) 0.0516(4) Uani 1 d . . 
O4 O -0.4126(2) 0.35270(9) 0.6612(2) 0.0619(5) Uani 1 d . . 
C13 C -0.4592(4) 0.29824(15) 0.5577(3) 0.0725(8) Uani 1 d G . 
H13A H -0.5564(16) 0.2783(13) 0.5875(30) 0.109(4) Uiso 1 calc G . 
H13B H -0.3762(24) 0.2646(11) 0.5620(30) 0.109(4) Uiso 1 calc G . 
H13C H -0.4770(29) 0.3155(14) 0.4541(13) 0.109(4) Uiso 1 calc G . 
 
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 
N1 0.0365(10) 0.0416(10) 0.0420(9) 0.0031(7) 0.0060(7) 0.0026(7) 
C1 0.0381(11) 0.0418(11) 0.0385(11) -0.0012(8) 0.0031(9) 0.0028(9) 
C2 0.0400(12) 0.0419(11) 0.0361(10) -0.0029(8) 0.0068(9) 0.0016(9) 
C3 0.0368(11) 0.0440(11) 0.0411(11) -0.0049(9) 0.0088(9) 0.0003(8) 
C4 0.0355(12) 0.0490(12) 0.0392(11) -0.0038(9) 0.0065(9) 0.0059(9) 
C5 0.0448(14) 0.072(2) 0.0509(13) 0.0076(11) 0.0040(10) 0.0138(11) 
C6 0.0401(12) 0.0469(12) 0.0497(12) 0.0041(10) 0.0011(10) 0.0047(9) 
S1 0.0370(4) 0.0642(5) 0.0921(6) 0.0226(3) 0.0047(3) -0.0025(3) 
C7 0.0465(12) 0.0447(12) 0.0452(12) 0.0013(9) 0.0089(9) 0.0002(10) 
C8 0.075(2) 0.0503(14) 0.0486(13) -0.0017(10) 0.0083(12) 0.0105(12) 
C9 0.0550(14) 0.0436(13) 0.0575(14) -0.0021(10) 0.0063(11) 0.0024(11) 
O1 0.124(2) 0.0672(13) 0.0785(13) -0.0035(10) 0.0157(12) 0.0411(13) 
O2 0.0681(11) 0.0505(9) 0.0550(10) 0.0078(7) 0.0053(8) 0.0051(8) 
C10 0.078(2) 0.068(2) 0.076(2) 0.0225(14) -0.0044(14) 0.0018(15) 
C11 0.0385(13) 0.0555(13) 0.0560(13) -0.0050(10) 0.0126(10) -0.0030(10) 
C12 0.0339(11) 0.0475(12) 0.0469(12) 0.0092(9) 0.0025(9) -0.0016(9) 
O3 0.0498(10) 0.0570(9) 0.0493(9) -0.0027(7) 0.0120(7) -0.0054(7) 
O4 0.0417(9) 0.0739(12) 0.0709(11) -0.0078(9) 0.0096(8) -0.0164(8) 
C13 0.065(2) 0.077(2) 0.074(2) -0.0051(14) -0.0014(14) -0.0295(14) 
 
_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 
N1 C4 1.349(3) . ? 
N1 C1 1.387(3) . ? 
C1 C6 1.400(3) . ? 
C1 C2 1.407(3) . ? 
C2 C3 1.397(3) . ? 
C2 C7 1.501(3) . ? 
C3 C4 1.393(3) . ? 
C3 C11 1.501(3) . ? 
C4 C5 1.493(3) . ? 
C6 S1 1.642(2) . ? 
C7 C8 1.511(3) . ? 
C8 C9 1.491(3) . ? 
C9 O1 1.199(3) . ? 
C9 O2 1.332(3) . ? 
O2 C10 1.446(3) . ? 
C11 C12 1.501(3) . ? 
C12 O3 1.199(3) . ? 
C12 O4 1.340(3) . ? 
O4 C13 1.432(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 
C4 N1 C1 109.6(2) . . ? 
N1 C1 C6 123.4(2) . . ? 
N1 C1 C2 107.1(2) . . ? 
C6 C1 C2 129.5(2) . . ? 
C3 C2 C1 107.1(2) . . ? 
C3 C2 C7 128.4(2) . . ? 
C1 C2 C7 124.5(2) . . ? 
C4 C3 C2 107.8(2) . . ? 
C4 C3 C11 125.5(2) . . ? 
C2 C3 C11 126.7(2) . . ? 
N1 C4 C3 108.4(2) . . ? 
N1 C4 C5 120.9(2) . . ? 
C3 C4 C5 130.7(2) . . ? 
C1 C6 S1 127.8(2) . . ? 
C2 C7 C8 111.3(2) . . ? 
C9 C8 C7 118.1(2) . . ? 
O1 C9 O2 123.2(2) . . ? 
O1 C9 C8 123.2(2) . . ? 
O2 C9 C8 113.6(2) . . ? 
C9 O2 C10 115.6(2) . . ? 
C12 C11 C3 115.0(2) . . ? 
O3 C12 O4 123.4(2) . . ? 
O3 C12 C11 126.9(2) . . ? 
O4 C12 C11 109.8(2) . . ? 
C12 O4 C13 116.5(2) . . ? 
 
_refine_diff_density_max    0.328 
_refine_diff_density_min   -0.294 
_refine_diff_density_rms    0.055 
