 
data_lyj5 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety           'C17 H15 N O4 S'
_chemical_formula_sum 
 'C17 H15 N O4 S' 
_chemical_formula_weight          329.36 
 
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    'P 21 21 21' 
 
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                    8.3958(4) 
_cell_length_b                    9.7344(5) 
_cell_length_c                    18.4678(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1509.34(13) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used      3184 
_cell_measurement_theta_min       3.8740 
_cell_measurement_theta_max       27.8850 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.17 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.449 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              688 
_exptl_absorpt_coefficient_mu     0.235 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9612 
_exptl_absorpt_correction_T_max   0.9769 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(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   'SuperNova, Dual, Cu at zero, Atlas' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             5829 
_diffrn_reflns_av_R_equivalents   0.0405 
_diffrn_reflns_av_sigmaI/netI     0.0564 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          3.39 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              2885 
_reflns_number_gt                 2614 
_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 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)+(0.0470P)²+0.3254P] 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    -0.08(9)
_chemical_absolute_configuration  R 
_refine_ls_number_reflns          2885 
_refine_ls_number_parameters      208 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0464 
_refine_ls_R_factor_gt            0.0399 
_refine_ls_wR_factor_ref          0.1009 
_refine_ls_wR_factor_gt           0.0936 
_refine_ls_goodness_of_fit_ref    1.026 
_refine_ls_restrained_S_all       1.026 
_refine_ls_shift/su_max           0.003 
_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 0.31935(8) 0.36351(7) 0.60893(3) 0.02586(18) Uani 1 1 d . . . 
O1 O 0.2913(2) 0.3491(2) 0.53323(9) 0.0368(5) Uani 1 1 d . . . 
N1 N 0.2625(3) 0.5184(2) 0.63779(11) 0.0216(5) Uani 1 1 d . . . 
C1 C 0.5332(3) 0.4943(3) 0.67939(13) 0.0208(5) Uani 1 1 d . . . 
O2 O 0.2528(3) 0.2651(2) 0.65736(11) 0.0350(5) Uani 1 1 d . . . 
C2 C 0.6824(3) 0.5291(3) 0.70500(12) 0.0226(5) Uani 1 1 d . . . 
H2B H 0.6945 0.6000 0.7399 0.027 Uiso 1 1 calc R . . 
O3 O 0.4003(2) 0.48411(19) 0.82003(9) 0.0264(4) Uani 1 1 d . . . 
C3 C 0.8140(3) 0.4594(3) 0.67904(13) 0.0270(6) Uani 1 1 d . . . 
H3A H 0.9173 0.4854 0.6950 0.032 Uiso 1 1 calc R . . 
O4 O 0.1571(2) 0.53160(18) 0.77667(9) 0.0242(4) Uani 1 1 d . . . 
C4 C 0.7979(3) 0.3519(3) 0.63002(13) 0.0273(6) Uani 1 1 d . . . 
H4A H 0.8899 0.3046 0.6134 0.033 Uiso 1 1 calc R . . 
C5 C 0.6501(3) 0.3133(3) 0.60534(13) 0.0252(6) Uani 1 1 d . . . 
H5A H 0.6373 0.2389 0.5726 0.030 Uiso 1 1 calc R . . 
C6 C 0.5211(3) 0.3875(3) 0.63027(13) 0.0234(6) Uani 1 1 d . . . 
C7 C 0.3739(3) 0.5616(2) 0.69695(12) 0.0195(5) Uani 1 1 d . . . 
C8 C 0.3127(3) 0.5178(2) 0.77188(12) 0.0205(5) Uani 1 1 d . . . 
C9 C 0.0854(3) 0.4837(3) 0.84451(13) 0.0277(6) Uani 1 1 d . . . 
H9A H -0.0215 0.5252 0.8506 0.033 Uiso 1 1 calc R . . 
H9B H 0.1524 0.5122 0.8860 0.033 Uiso 1 1 calc R . . 
C10 C 0.0718(3) 0.3306(3) 0.84271(15) 0.0327(7) Uani 1 1 d . . . 
H10A H 0.0239 0.2981 0.8880 0.049 Uiso 1 1 calc R . . 
H10B H 0.1780 0.2901 0.8371 0.049 Uiso 1 1 calc R . . 
H10C H 0.0046 0.3031 0.8018 0.049 Uiso 1 1 calc R . . 
C11 C 0.3788(3) 0.7197(2) 0.69333(13) 0.0235(6) Uani 1 1 d . . . 
H11A H 0.3103 0.7613 0.7310 0.028 Uiso 1 1 calc R . . 
H11B H 0.4889 0.7545 0.6990 0.028 Uiso 1 1 calc R . . 
C12 C 0.3157(3) 0.7487(3) 0.61881(12) 0.0237(5) Uani 1 1 d . . . 
C13 C 0.3067(3) 0.8745(3) 0.58263(14) 0.0300(6) Uani 1 1 d . . . 
H13A H 0.3487 0.9560 0.6036 0.036 Uiso 1 1 calc R . . 
C14 C 0.2346(3) 0.8765(3) 0.51519(15) 0.0363(7) Uani 1 1 d . . . 
H14A H 0.2290 0.9603 0.4890 0.044 Uiso 1 1 calc R . . 
C15 C 0.1711(4) 0.7594(3) 0.48570(14) 0.0369(7) Uani 1 1 d . . . 
H15A H 0.1226 0.7640 0.4393 0.044 Uiso 1 1 calc R . . 
C16 C 0.1756(3) 0.6346(3) 0.52165(12) 0.0296(6) Uani 1 1 d . . . 
H16A H 0.1287 0.5542 0.5017 0.036 Uiso 1 1 calc R . . 
C17 C 0.2523(3) 0.6328(3) 0.58839(12) 0.0236(5) Uani 1 1 d . . . 
 
 
_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 1.425(2) . ? 
S1 O1 1.4247(18) . ? 
S1 N1 1.669(2) . ? 
S1 C6 1.755(3) . ? 
N1 C17 1.442(3) . ? 
N1 C7 1.498(3) . ? 
C1 C2 1.382(4) . ? 
C1 C6 1.383(4) . ? 
C1 C7 1.524(3) . ? 
C2 C3 1.382(4) . ? 
C2 H2B 0.9500 . ? 
O3 C8 1.200(3) . ? 
C3 C4 1.390(4) . ? 
C3 H3A 0.9500 . ? 
O4 C8 1.316(3) . ? 
O4 C9 1.466(3) . ? 
C4 C5 1.374(4) . ? 
C4 H4A 0.9500 . ? 
C5 C6 1.381(3) . ? 
C5 H5A 0.9500 . ? 
C7 C8 1.537(3) . ? 
C7 C11 1.541(3) . ? 
C9 C10 1.496(4) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C11 C12 1.501(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C17 1.369(4) . ? 
C12 C13 1.397(3) . ? 
C13 C14 1.385(4) . ? 
C13 H13A 0.9500 . ? 
C14 C15 1.371(5) . ? 
C14 H14A 0.9500 . ? 
C15 C16 1.385(4) . ? 
C15 H15A 0.9500 . ? 
C16 C17 1.391(3) . ? 
C16 H16A 0.9500 . ? 
 
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 119.03(13) . . ? 
O2 S1 N1 107.15(11) . . ? 
O1 S1 N1 110.79(11) . . ? 
O2 S1 C6 109.09(12) . . ? 
O1 S1 C6 113.13(12) . . ? 
N1 S1 C6 94.82(12) . . ? 
C17 N1 C7 106.37(19) . . ? 
C17 N1 S1 120.82(16) . . ? 
C7 N1 S1 107.92(15) . . ? 
C2 C1 C6 118.4(2) . . ? 
C2 C1 C7 128.1(2) . . ? 
C6 C1 C7 113.5(2) . . ? 
C3 C2 C1 119.1(2) . . ? 
C3 C2 H2B 120.5 . . ? 
C1 C2 H2B 120.5 . . ? 
C2 C3 C4 121.2(2) . . ? 
C2 C3 H3A 119.4 . . ? 
C4 C3 H3A 119.4 . . ? 
C8 O4 C9 115.62(19) . . ? 
C5 C4 C3 120.6(2) . . ? 
C5 C4 H4A 119.7 . . ? 
C3 C4 H4A 119.7 . . ? 
C4 C5 C6 117.1(2) . . ? 
C4 C5 H5A 121.5 . . ? 
C6 C5 H5A 121.5 . . ? 
C5 C6 C1 123.7(2) . . ? 
C5 C6 S1 127.8(2) . . ? 
C1 C6 S1 108.54(18) . . ? 
N1 C7 C1 105.78(19) . . ? 
N1 C7 C8 111.72(19) . . ? 
C1 C7 C8 111.5(2) . . ? 
N1 C7 C11 105.4(2) . . ? 
C1 C7 C11 113.3(2) . . ? 
C8 C7 C11 109.0(2) . . ? 
O3 C8 O4 125.9(2) . . ? 
O3 C8 C7 122.6(2) . . ? 
O4 C8 C7 111.3(2) . . ? 
O4 C9 C10 109.2(2) . . ? 
O4 C9 H9A 109.8 . . ? 
C10 C9 H9A 109.8 . . ? 
O4 C9 H9B 109.8 . . ? 
C10 C9 H9B 109.8 . . ? 
H9A C9 H9B 108.3 . . ? 
C9 C10 H10A 109.5 . . ? 
C9 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C9 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C11 C7 102.6(2) . . ? 
C12 C11 H11A 111.2 . . ? 
C7 C11 H11A 111.2 . . ? 
C12 C11 H11B 111.2 . . ? 
C7 C11 H11B 111.2 . . ? 
H11A C11 H11B 109.2 . . ? 
C17 C12 C13 120.4(2) . . ? 
C17 C12 C11 111.0(2) . . ? 
C13 C12 C11 128.5(2) . . ? 
C14 C13 C12 117.8(3) . . ? 
C14 C13 H13A 121.1 . . ? 
C12 C13 H13A 121.1 . . ? 
C15 C14 C13 121.0(3) . . ? 
C15 C14 H14A 119.5 . . ? 
C13 C14 H14A 119.5 . . ? 
C14 C15 C16 121.9(2) . . ? 
C14 C15 H15A 119.1 . . ? 
C16 C15 H15A 119.1 . . ? 
C15 C16 C17 116.7(3) . . ? 
C15 C16 H16A 121.7 . . ? 
C17 C16 H16A 121.7 . . ? 
C12 C17 C16 122.2(3) . . ? 
C12 C17 N1 110.7(2) . . ? 
C16 C17 N1 126.7(3) . . ? 
 
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 C17 -154.7(2) . . . . ? 
O1 S1 N1 C17 -23.4(2) . . . . ? 
C6 S1 N1 C17 93.6(2) . . . . ? 
O2 S1 N1 C7 82.72(17) . . . . ? 
O1 S1 N1 C7 -145.96(16) . . . . ? 
C6 S1 N1 C7 -28.97(17) . . . . ? 
C6 C1 C2 C3 2.0(3) . . . . ? 
C7 C1 C2 C3 -176.4(2) . . . . ? 
C1 C2 C3 C4 -2.5(3) . . . . ? 
C2 C3 C4 C5 0.9(4) . . . . ? 
C3 C4 C5 C6 1.2(4) . . . . ? 
C4 C5 C6 C1 -1.7(4) . . . . ? 
C4 C5 C6 S1 -179.98(19) . . . . ? 
C2 C1 C6 C5 0.1(4) . . . . ? 
C7 C1 C6 C5 178.7(2) . . . . ? 
C2 C1 C6 S1 178.63(18) . . . . ? 
C7 C1 C6 S1 -2.7(3) . . . . ? 
O2 S1 C6 C5 87.3(2) . . . . ? 
O1 S1 C6 C5 -47.6(3) . . . . ? 
N1 S1 C6 C5 -162.7(2) . . . . ? 
O2 S1 C6 C1 -91.2(2) . . . . ? 
O1 S1 C6 C1 133.91(18) . . . . ? 
N1 S1 C6 C1 18.86(19) . . . . ? 
C17 N1 C7 C1 -100.8(2) . . . . ? 
S1 N1 C7 C1 30.3(2) . . . . ? 
C17 N1 C7 C8 137.8(2) . . . . ? 
S1 N1 C7 C8 -91.2(2) . . . . ? 
C17 N1 C7 C11 19.6(3) . . . . ? 
S1 N1 C7 C11 150.57(17) . . . . ? 
C2 C1 C7 N1 161.2(2) . . . . ? 
C6 C1 C7 N1 -17.3(3) . . . . ? 
C2 C1 C7 C8 -77.2(3) . . . . ? 
C6 C1 C7 C8 104.4(2) . . . . ? 
C2 C1 C7 C11 46.3(3) . . . . ? 
C6 C1 C7 C11 -132.2(2) . . . . ? 
C9 O4 C8 O3 -8.5(4) . . . . ? 
C9 O4 C8 C7 176.07(19) . . . . ? 
N1 C7 C8 O3 145.8(2) . . . . ? 
C1 C7 C8 O3 27.7(3) . . . . ? 
C11 C7 C8 O3 -98.2(3) . . . . ? 
N1 C7 C8 O4 -38.6(3) . . . . ? 
C1 C7 C8 O4 -156.7(2) . . . . ? 
C11 C7 C8 O4 77.5(3) . . . . ? 
C8 O4 C9 C10 -78.5(3) . . . . ? 
N1 C7 C11 C12 -18.2(3) . . . . ? 
C1 C7 C11 C12 97.0(2) . . . . ? 
C8 C7 C11 C12 -138.3(2) . . . . ? 
C7 C11 C12 C17 10.9(3) . . . . ? 
C7 C11 C12 C13 -173.5(3) . . . . ? 
C17 C12 C13 C14 -1.1(4) . . . . ? 
C11 C12 C13 C14 -176.3(3) . . . . ? 
C12 C13 C14 C15 1.4(4) . . . . ? 
C13 C14 C15 C16 0.1(4) . . . . ? 
C14 C15 C16 C17 -1.9(4) . . . . ? 
C13 C12 C17 C16 -0.8(4) . . . . ? 
C11 C12 C17 C16 175.2(2) . . . . ? 
C13 C12 C17 N1 -174.8(2) . . . . ? 
C11 C12 C17 N1 1.2(3) . . . . ? 
C15 C16 C17 C12 2.2(4) . . . . ? 
C15 C16 C17 N1 175.3(2) . . . . ? 
C7 N1 C17 C12 -13.3(3) . . . . ? 
S1 N1 C17 C12 -136.59(19) . . . . ? 
C7 N1 C17 C16 172.9(2) . . . . ? 
S1 N1 C17 C16 49.7(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.989 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.989 
_refine_diff_density_max    0.317 
_refine_diff_density_min   -0.276 
_refine_diff_density_rms    0.054 
