 
data_a1 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C16 H13 N O2 S'
_chemical_formula_sum             'C16 H13 N O2 S' 
_chemical_formula_weight          283.33 
 
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    'P 21/c'
_symmetry_space_group_name_Hall   '-P 2ybc'
 
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                    7.2703(14) 
_cell_length_b                    23.841(5) 
_cell_length_c                    7.9637(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.852(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1345.8(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     4489 
_cell_measurement_theta_min       2.76 
_cell_measurement_theta_max       26.96 
 
_exptl_crystal_description        'Rodlike' 
_exptl_crystal_colour             'Colorless' 
_exptl_crystal_size_max           0.22 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.398 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              592 
_exptl_absorpt_coefficient_mu     0.240 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9490 
_exptl_absorpt_correction_T_max   0.9535 
_exptl_absorpt_process_details    'SADABS (Bruker, 2005)' 
 
_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 APEX2 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             9446 
_diffrn_reflns_av_R_equivalents   0.0266 
_diffrn_reflns_av_sigmaI/netI     0.0217 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -28 
_diffrn_reflns_limit_k_max        28 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          1.71 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              2373 
_reflns_number_gt                 2116 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'APEX2 (Bruker, 2005)'  
_computing_cell_refinement        'SAINT (Bruker, 2005)' 
_computing_data_reduction         'SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material   '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)+(0.0635P)²+0.5742P] 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          2373 
_refine_ls_number_parameters      183 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0452 
_refine_ls_R_factor_gt            0.0407 
_refine_ls_wR_factor_ref          0.1160 
_refine_ls_wR_factor_gt           0.1126 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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 0.14513(7) 0.56310(2) 0.33159(6) 0.04202(19) Uani 1 1 d . . . 
C1 C 0.2675(3) 0.59049(7) 0.6476(2) 0.0374(4) Uani 1 1 d . . . 
C9 C 0.2025(2) 0.42990(8) 0.2878(2) 0.0356(4) Uani 1 1 d . . . 
C8 C 0.2589(2) 0.45317(8) 0.4520(2) 0.0331(4) Uani 1 1 d . . . 
C13 C 0.3327(3) 0.41711(8) 0.5892(2) 0.0373(4) Uani 1 1 d . . . 
H4 H 0.3717 0.4322 0.6991 0.045 Uiso 1 1 calc R . . 
C7 C 0.2425(2) 0.51341(7) 0.4888(2) 0.0333(4) Uani 1 1 d . . . 
C10 C 0.2128(3) 0.37209(8) 0.2641(2) 0.0416(4) Uani 1 1 d . . . 
C12 C 0.3499(3) 0.35993(8) 0.5681(2) 0.0413(4) Uani 1 1 d . . . 
C6 C 0.1846(3) 0.61460(8) 0.4884(3) 0.0409(4) Uani 1 1 d . . . 
C11 C 0.2870(3) 0.33784(8) 0.4044(3) 0.0445(5) Uani 1 1 d . . . 
H9 H 0.2946 0.2994 0.3879 0.053 Uiso 1 1 calc R . . 
C2 C 0.3127(3) 0.62445(9) 0.7945(3) 0.0473(5) Uani 1 1 d . . . 
H10 H 0.3673 0.6091 0.9013 0.057 Uiso 1 1 calc R . . 
C5 C 0.1436(3) 0.67174(9) 0.4740(3) 0.0506(5) Uani 1 1 d . . . 
H11 H 0.0862 0.6874 0.3684 0.061 Uiso 1 1 calc R . . 
C3 C 0.2747(3) 0.68095(9) 0.7781(3) 0.0530(5) Uani 1 1 d . . . 
H12 H 0.3060 0.7039 0.8746 0.064 Uiso 1 1 calc R . . 
C15 C 0.2629(3) 0.47726(10) 0.0447(3) 0.0530(5) Uani 1 1 d . . . 
H13A H 0.3776 0.4914 0.1162 0.080 Uiso 1 1 calc R . . 
H13B H 0.2094 0.5051 -0.0390 0.080 Uiso 1 1 calc R . . 
H13C H 0.2895 0.4439 -0.0133 0.080 Uiso 1 1 calc R . . 
C14 C 0.4327(4) 0.32289(9) 0.7203(3) 0.0597(6) Uani 1 1 d . . . 
H14A H 0.5620 0.3332 0.7654 0.090 Uiso 1 1 calc R . . 
H14B H 0.4264 0.2844 0.6841 0.090 Uiso 1 1 calc R . . 
H14C H 0.3624 0.3276 0.8080 0.090 Uiso 1 1 calc R . . 
C4 C 0.1902(3) 0.70423(9) 0.6195(3) 0.0564(6) Uani 1 1 d . . . 
H15 H 0.1648 0.7425 0.6120 0.068 Uiso 1 1 calc R . . 
C16 C 0.1376(3) 0.34684(10) 0.0920(3) 0.0596(6) Uani 1 1 d . . . 
H16 H 0.0712 0.3704 0.0067 0.072 Uiso 1 1 calc R . . 
N1 N 0.2983(2) 0.53322(6) 0.64412(19) 0.0378(4) Uani 1 1 d . . . 
O1 O 0.13110(18) 0.46427(6) 0.14984(16) 0.0424(3) Uani 1 1 d . . . 
O2 O 0.1543(3) 0.29982(9) 0.0539(3) 0.0912(6) 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 C6 1.729(2) . ? 
S1 C7 1.7542(18) . ? 
C1 N1 1.385(2) . ? 
C1 C2 1.400(3) . ? 
C1 C6 1.401(3) . ? 
C9 O1 1.376(2) . ? 
C9 C8 1.395(2) . ? 
C9 C10 1.396(3) . ? 
C8 C13 1.400(3) . ? 
C8 C7 1.476(3) . ? 
C13 C12 1.383(3) . ? 
C13 H4 0.9300 . ? 
C7 N1 1.302(2) . ? 
C10 C11 1.392(3) . ? 
C10 C16 1.485(3) . ? 
C12 C11 1.386(3) . ? 
C12 C14 1.512(3) . ? 
C6 C5 1.394(3) . ? 
C11 H9 0.9300 . ? 
C2 C3 1.375(3) . ? 
C2 H10 0.9300 . ? 
C5 C4 1.373(3) . ? 
C5 H11 0.9300 . ? 
C3 C4 1.391(3) . ? 
C3 H12 0.9300 . ? 
C15 O1 1.439(2) . ? 
C15 H13A 0.9600 . ? 
C15 H13B 0.9600 . ? 
C15 H13C 0.9600 . ? 
C14 H14A 0.9600 . ? 
C14 H14B 0.9600 . ? 
C14 H14C 0.9600 . ? 
C4 H15 0.9300 . ? 
C16 O2 1.175(3) . ? 
C16 H16 0.9300 . ? 
 
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 
C6 S1 C7 89.34(9) . . ? 
N1 C1 C2 125.30(17) . . ? 
N1 C1 C6 115.19(16) . . ? 
C2 C1 C6 119.51(17) . . ? 
O1 C9 C8 119.43(16) . . ? 
O1 C9 C10 120.12(16) . . ? 
C8 C9 C10 120.42(17) . . ? 
C9 C8 C13 117.97(17) . . ? 
C9 C8 C7 123.58(16) . . ? 
C13 C8 C7 118.45(16) . . ? 
C12 C13 C8 122.66(17) . . ? 
C12 C13 H4 118.7 . . ? 
C8 C13 H4 118.7 . . ? 
N1 C7 C8 121.32(16) . . ? 
N1 C7 S1 115.09(13) . . ? 
C8 C7 S1 123.58(13) . . ? 
C11 C10 C9 119.56(17) . . ? 
C11 C10 C16 120.01(19) . . ? 
C9 C10 C16 120.38(19) . . ? 
C13 C12 C11 117.99(18) . . ? 
C13 C12 C14 120.58(18) . . ? 
C11 C12 C14 121.42(18) . . ? 
C5 C6 C1 121.13(19) . . ? 
C5 C6 S1 129.54(16) . . ? 
C1 C6 S1 109.33(14) . . ? 
C12 C11 C10 121.33(18) . . ? 
C12 C11 H9 119.3 . . ? 
C10 C11 H9 119.3 . . ? 
C3 C2 C1 118.8(2) . . ? 
C3 C2 H10 120.6 . . ? 
C1 C2 H10 120.6 . . ? 
C4 C5 C6 118.3(2) . . ? 
C4 C5 H11 120.9 . . ? 
C6 C5 H11 120.9 . . ? 
C2 C3 C4 121.1(2) . . ? 
C2 C3 H12 119.5 . . ? 
C4 C3 H12 119.5 . . ? 
O1 C15 H13A 109.5 . . ? 
O1 C15 H13B 109.5 . . ? 
H13A C15 H13B 109.5 . . ? 
O1 C15 H13C 109.5 . . ? 
H13A C15 H13C 109.5 . . ? 
H13B C15 H13C 109.5 . . ? 
C12 C14 H14A 109.5 . . ? 
C12 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C12 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C5 C4 C3 121.2(2) . . ? 
C5 C4 H15 119.4 . . ? 
C3 C4 H15 119.4 . . ? 
O2 C16 C10 126.0(3) . . ? 
O2 C16 H16 117.0 . . ? 
C10 C16 H16 117.0 . . ? 
C7 N1 C1 111.05(15) . . ? 
C9 O1 C15 114.26(14) . . ? 
 
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 
O1 C9 C8 C13 -179.35(15) . . . . ? 
C10 C9 C8 C13 2.6(3) . . . . ? 
O1 C9 C8 C7 1.5(3) . . . . ? 
C10 C9 C8 C7 -176.54(16) . . . . ? 
C9 C8 C13 C12 -0.6(3) . . . . ? 
C7 C8 C13 C12 178.66(17) . . . . ? 
C9 C8 C7 N1 -179.52(16) . . . . ? 
C13 C8 C7 N1 1.3(3) . . . . ? 
C9 C8 C7 S1 1.5(2) . . . . ? 
C13 C8 C7 S1 -177.63(13) . . . . ? 
C6 S1 C7 N1 0.37(15) . . . . ? 
C6 S1 C7 C8 179.37(15) . . . . ? 
O1 C9 C10 C11 179.36(16) . . . . ? 
C8 C9 C10 C11 -2.6(3) . . . . ? 
O1 C9 C10 C16 -3.3(3) . . . . ? 
C8 C9 C10 C16 174.75(17) . . . . ? 
C8 C13 C12 C11 -1.5(3) . . . . ? 
C8 C13 C12 C14 179.29(18) . . . . ? 
N1 C1 C6 C5 179.18(18) . . . . ? 
C2 C1 C6 C5 -0.9(3) . . . . ? 
N1 C1 C6 S1 0.1(2) . . . . ? 
C2 C1 C6 S1 179.95(14) . . . . ? 
C7 S1 C6 C5 -179.3(2) . . . . ? 
C7 S1 C6 C1 -0.22(14) . . . . ? 
C13 C12 C11 C10 1.5(3) . . . . ? 
C14 C12 C11 C10 -179.28(19) . . . . ? 
C9 C10 C11 C12 0.5(3) . . . . ? 
C16 C10 C11 C12 -176.88(19) . . . . ? 
N1 C1 C2 C3 179.63(18) . . . . ? 
C6 C1 C2 C3 -0.3(3) . . . . ? 
C1 C6 C5 C4 1.3(3) . . . . ? 
S1 C6 C5 C4 -179.76(17) . . . . ? 
C1 C2 C3 C4 1.0(3) . . . . ? 
C6 C5 C4 C3 -0.5(3) . . . . ? 
C2 C3 C4 C5 -0.6(3) . . . . ? 
C11 C10 C16 O2 -10.1(4) . . . . ? 
C9 C10 C16 O2 172.5(2) . . . . ? 
C8 C7 N1 C1 -179.43(15) . . . . ? 
S1 C7 N1 C1 -0.4(2) . . . . ? 
C2 C1 N1 C7 -179.67(17) . . . . ? 
C6 C1 N1 C7 0.2(2) . . . . ? 
C8 C9 O1 C15 101.8(2) . . . . ? 
C10 C9 O1 C15 -80.1(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.682 
_refine_diff_density_min   -0.255 
_refine_diff_density_rms    0.059 
