 
data_pb113 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H15 N3 O S2' 
_chemical_formula_weight          329.43 
 
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    'C 2/c' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
 
_cell_length_a                    16.1495(7) 
_cell_length_b                    12.7748(5) 
_cell_length_c                    16.1233(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  111.003(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      3105.3(2) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3060 
_cell_measurement_theta_min       2.09 
_cell_measurement_theta_max       28.36 
 
_exptl_crystal_description        'rod' 
_exptl_crystal_colour             'pale yellow' 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.409 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1376 
_exptl_absorpt_coefficient_mu     0.347 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(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   'Bruker APEX II CCD' 
_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             22185 
_diffrn_reflns_av_R_equivalents   0.1099 
_diffrn_reflns_av_sigmaI/netI     0.0482 
_diffrn_reflns_limit_h_min        -21 
_diffrn_reflns_limit_h_max        21 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.09 
_diffrn_reflns_theta_max          28.36 
_reflns_number_total              3879 
_reflns_number_gt                 3060 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'APEX II v.2.2 (Bruker, 2007)' 
_computing_cell_refinement        'APEX II v.2.2 (Bruker, 2007)' 
_computing_data_reduction         'APEX II v.2.2 (Bruker, 2007)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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)+(0.1000P)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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3879 
_refine_ls_number_parameters      256 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0739 
_refine_ls_R_factor_gt            0.0579 
_refine_ls_wR_factor_ref          0.1969 
_refine_ls_wR_factor_gt           0.1717 
_refine_ls_goodness_of_fit_ref    1.407 
_refine_ls_restrained_S_all       1.407 
_refine_ls_shift/su_max           0.035 
_refine_ls_shift/su_mean          0.002 
 
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 0.23454(4) 0.45752(5) 0.22893(4) 0.0584(2) Uani 1 1 d . . . 
S2 S 0.14459(5) 0.28401(5) 0.28279(4) 0.0620(2) Uani 1 1 d . . . 
N2 N -0.06045(10) 0.70194(12) 0.08285(10) 0.0385(4) Uani 1 1 d . . . 
N1 N -0.13129(12) 0.73774(14) 0.01746(11) 0.0484(4) Uani 1 1 d . . . 
N3 N -0.00714(14) 0.77386(13) 0.13504(12) 0.0542(5) Uani 1 1 d . . . 
O1 O 0.09063(9) 0.62383(10) 0.22627(8) 0.0437(3) Uani 1 1 d . . . 
H1 H 0.0740 0.6846 0.2149 0.065 Uiso 1 1 calc R . . 
C5 C -0.09568(12) 0.52194(15) 0.03502(11) 0.0377(4) Uani 1 1 d . . . 
C4 C -0.04058(11) 0.59305(14) 0.09494(11) 0.0355(4) Uani 1 1 d . . . 
C7 C -0.04669(16) 0.86508(16) 0.10043(14) 0.0524(5) Uani 1 1 d . . . 
C2 C 0.05218(12) 0.45172(14) 0.17486(11) 0.0364(4) Uani 1 1 d . . . 
C15 C 0.2105(3) 0.2500(3) 0.2188(2) 0.0831(9) Uani 1 1 d . . . 
C3 C 0.03386(12) 0.55901(14) 0.16551(11) 0.0345(4) Uani 1 1 d . . . 
C13 C 0.13487(14) 0.41991(16) 0.25198(12) 0.0440(4) Uani 1 1 d . . . 
C8 C -0.12304(15) 0.84244(17) 0.02812(14) 0.0495(5) Uani 1 1 d . . . 
C9 C -0.1785(2) 0.9237(2) -0.02260(19) 0.0679(7) Uani 1 1 d . . . 
C1 C -0.00343(13) 0.38232(14) 0.11519(12) 0.0405(4) Uani 1 1 d . . . 
C6 C -0.07838(13) 0.41624(15) 0.04461(11) 0.0392(4) Uani 1 1 d . . . 
C11 C -0.0753(3) 1.0455(2) 0.0763(2) 0.0876(10) Uani 1 1 d . . . 
C14 C 0.2786(3) 0.3286(3) 0.2285(4) 0.0971(12) Uani 1 1 d . . . 
C10 C -0.1536(2) 1.0224(2) 0.0028(2) 0.0792(8) Uani 1 1 d . . . 
C12 C -0.0212(3) 0.9692(2) 0.1266(2) 0.0814(9) Uani 1 1 d . . . 
C16 C -0.13830(18) 0.33866(19) -0.01862(15) 0.0514(5) Uani 1 1 d . . . 
H7 H 0.035(2) 0.990(2) 0.1726(19) 0.075(9) Uiso 1 1 d . . . 
H5 H -0.190(2) 1.087(3) -0.034(2) 0.093(10) Uiso 1 1 d . . . 
H11 H 0.235(2) 0.182(3) 0.242(2) 0.083(9) Uiso 1 1 d . . . 
H2 H 0.0058(18) 0.301(2) 0.1236(16) 0.058(7) Uiso 1 1 d . . . 
H3 H -0.143(2) 0.552(2) -0.0091(19) 0.074(8) Uiso 1 1 d . . . 
H4 H -0.235(3) 0.909(3) -0.070(2) 0.085(9) Uiso 1 1 d . . . 
H8 H 0.1347(18) 0.4560(19) 0.3020(17) 0.052(6) Uiso 1 1 d . . . 
H14 H -0.107(3) 0.291(3) -0.037(2) 0.096(11) Uiso 1 1 d . . . 
H15 H -0.1679(18) 0.298(2) 0.0114(16) 0.055(7) Uiso 1 1 d . . . 
H13 H -0.187(3) 0.362(4) -0.072(3) 0.147(17) Uiso 1 1 d . . . 
H10 H 0.308(3) 0.317(4) 0.185(3) 0.120(13) Uiso 1 1 d . . . 
H6 H -0.066(2) 1.125(3) 0.091(2) 0.089(9) Uiso 1 1 d . . . 
H9 H 0.332(4) 0.309(5) 0.291(3) 0.156(18) Uiso 1 1 d . . . 
H12 H 0.159(11) 0.233(8) 0.154(9) 0.44(7) Uiso 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 C14 1.795(3) . ? 
S1 C13 1.841(2) . ? 
S2 C15 1.782(3) . ? 
S2 C13 1.797(2) . ? 
N2 N1 1.329(2) . ? 
N2 N3 1.332(2) . ? 
N2 C4 1.425(2) . ? 
N1 C8 1.349(3) . ? 
N3 C7 1.350(3) . ? 
O1 C3 1.357(2) . ? 
C5 C6 1.376(3) . ? 
C5 C4 1.391(2) . ? 
C4 C3 1.396(2) . ? 
C7 C8 1.390(3) . ? 
C7 C12 1.411(3) . ? 
C2 C1 1.378(3) . ? 
C2 C3 1.399(2) . ? 
C2 C13 1.518(3) . ? 
C15 C14 1.455(6) . ? 
C8 C9 1.422(3) . ? 
C9 C10 1.342(4) . ? 
C1 C6 1.400(3) . ? 
C6 C16 1.500(3) . ? 
C11 C12 1.364(4) . ? 
C11 C10 1.420(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 
C14 S1 C13 97.93(14) . . ? 
C15 S2 C13 94.96(13) . . ? 
N1 N2 N3 116.21(16) . . ? 
N1 N2 C4 122.15(15) . . ? 
N3 N2 C4 121.60(15) . . ? 
N2 N1 C8 102.86(16) . . ? 
N2 N3 C7 103.38(17) . . ? 
C6 C5 C4 120.61(16) . . ? 
C5 C4 C3 120.83(16) . . ? 
C5 C4 N2 119.08(15) . . ? 
C3 C4 N2 120.09(15) . . ? 
N3 C7 C8 108.24(18) . . ? 
N3 C7 C12 130.2(2) . . ? 
C8 C7 C12 121.5(2) . . ? 
C1 C2 C3 119.70(16) . . ? 
C1 C2 C13 124.16(16) . . ? 
C3 C2 C13 116.14(16) . . ? 
C14 C15 S2 110.8(3) . . ? 
O1 C3 C4 124.06(16) . . ? 
O1 C3 C2 117.25(15) . . ? 
C4 C3 C2 118.69(16) . . ? 
C2 C13 S2 116.69(15) . . ? 
C2 C13 S1 109.93(13) . . ? 
S2 C13 S1 108.17(11) . . ? 
N1 C8 C7 109.31(18) . . ? 
N1 C8 C9 129.6(2) . . ? 
C7 C8 C9 121.1(2) . . ? 
C10 C9 C8 116.9(3) . . ? 
C2 C1 C6 121.71(17) . . ? 
C5 C6 C1 118.45(17) . . ? 
C5 C6 C16 121.08(18) . . ? 
C1 C6 C16 120.47(18) . . ? 
C12 C11 C10 122.4(3) . . ? 
C15 C14 S1 110.4(2) . . ? 
C9 C10 C11 122.0(3) . . ? 
C11 C12 C7 116.1(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              28.36 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.681 
_refine_diff_density_min   -0.633 
_refine_diff_density_rms    0.172 
