 
data_01sot057 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H22 N2 O2 S' 
_chemical_formula_weight          306.42 
 
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    C2/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                    12.8588(2) 
_cell_length_b                    10.7382(2) 
_cell_length_c                    23.1122(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.811(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      3184.28(9) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     7530
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.278 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1312 
_exptl_absorpt_coefficient_mu     0.210 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9593 
_exptl_absorpt_correction_T_max   0.9593 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1998)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8166 
_diffrn_reflns_av_R_equivalents   0.0554 
_diffrn_reflns_av_sigmaI/netI     0.0544 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        27 
_diffrn_reflns_theta_min          2.98 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              2784 
_reflns_number_gt                 2306 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_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)+(0.0493P)²+0.7825P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     difmap
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0023(5) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2784 
_refine_ls_number_parameters      279 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0492 
_refine_ls_R_factor_gt            0.0376 
_refine_ls_wR_factor_ref          0.0986 
_refine_ls_wR_factor_gt           0.0928 
_refine_ls_goodness_of_fit_ref    1.055 
_refine_ls_restrained_S_all       1.055 
_refine_ls_shift/su_max           0.004 
_refine_ls_shift/su_mean          0.001 
 
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 0.43208(3) 0.01335(4) 0.341113(16) 0.01980(18) Uani 1 1 d . . . 
N1 N 0.53206(11) -0.06940(15) 0.32441(6) 0.0192(4) Uani 1 1 d . . . 
N2 N 0.58695(10) -0.13013(14) 0.37203(5) 0.0194(4) Uani 1 1 d . . . 
O1 O 0.36349(9) -0.06334(12) 0.37163(5) 0.0256(3) Uani 1 1 d . . . 
O2 O 0.39592(9) 0.06968(13) 0.28698(5) 0.0263(3) Uani 1 1 d . . . 
C1 C 0.6453(2) 0.3823(3) 0.50715(11) 0.0460(6) Uani 1 1 d . . . 
C2 C 0.58623(15) 0.29496(19) 0.46560(8) 0.0291(5) Uani 1 1 d . . . 
C3 C 0.52525(14) 0.20004(18) 0.48614(8) 0.0256(4) Uani 1 1 d . . . 
C4 C 0.47310(14) 0.11720(18) 0.44827(7) 0.0223(4) Uani 1 1 d . . . 
C5 C 0.48182(13) 0.12978(17) 0.38905(7) 0.0199(4) Uani 1 1 d . . . 
C6 C 0.54001(15) 0.2262(2) 0.36772(8) 0.0313(5) Uani 1 1 d . . . 
C7 C 0.59203(17) 0.3075(2) 0.40585(8) 0.0360(5) Uani 1 1 d . . . 
C8 C 0.68679(13) -0.06908(18) 0.39223(7) 0.0214(4) Uani 1 1 d . . . 
C9 C 0.72957(15) -0.16644(19) 0.43597(7) 0.0249(4) Uani 1 1 d . . . 
C10 C 0.69300(15) -0.29103(19) 0.40801(8) 0.0261(4) Uani 1 1 d . . . 
C11 C 0.62103(13) -0.25655(17) 0.35427(7) 0.0216(4) Uani 1 1 d . . . 
C12 C 0.68281(14) -0.24522(19) 0.29947(7) 0.0253(4) Uani 1 1 d . . . 
C13 C 0.75725(14) -0.13684(19) 0.30088(7) 0.0265(5) Uani 1 1 d . . . 
C14 C 0.75796(15) -0.05402(19) 0.34356(7) 0.0255(4) Uani 1 1 d . . . 
C15 C 0.82754(18) -0.1270(3) 0.25181(9) 0.0392(6) Uani 1 1 d . . . 
C16 C 0.52886(16) -0.3424(2) 0.34442(9) 0.0296(5) Uani 1 1 d . . . 
H1A H 0.702(2) 0.410(3) 0.4907(10) 0.057(8) Uiso 1 1 d . . . 
H1B H 0.598(2) 0.447(3) 0.5213(11) 0.076(9) Uiso 1 1 d . . . 
H1C H 0.670(2) 0.339(3) 0.5451(12) 0.071(8) Uiso 1 1 d . . . 
H1N H 0.5671(17) -0.031(2) 0.3012(9) 0.034(6) Uiso 1 1 d . . . 
H3 H 0.5172(14) 0.1885(19) 0.5252(9) 0.029(5) Uiso 1 1 d . . . 
H4 H 0.4309(14) 0.0489(19) 0.4624(7) 0.020(5) Uiso 1 1 d . . . 
H6 H 0.5465(15) 0.234(2) 0.3280(9) 0.034(5) Uiso 1 1 d . . . 
H7 H 0.6374(19) 0.369(3) 0.3920(10) 0.057(7) Uiso 1 1 d . . . 
H8 H 0.6719(13) 0.0119(18) 0.4095(7) 0.015(4) Uiso 1 1 d . . . 
H9A H 0.8070(14) -0.1644(17) 0.4408(7) 0.019(4) Uiso 1 1 d . . . 
H9B H 0.7000(14) -0.1529(18) 0.4724(9) 0.026(5) Uiso 1 1 d . . . 
H10A H 0.6525(16) -0.339(2) 0.4354(9) 0.037(6) Uiso 1 1 d . . . 
H10B H 0.7531(15) -0.3438(19) 0.3981(7) 0.027(5) Uiso 1 1 d . . . 
H12A H 0.7199(16) -0.321(2) 0.2924(8) 0.041(6) Uiso 1 1 d . . . 
H12B H 0.6356(15) -0.235(2) 0.2651(9) 0.034(5) Uiso 1 1 d . . . 
H14 H 0.8069(15) 0.0101(19) 0.3421(8) 0.025(5) Uiso 1 1 d . . . 
H15A H 0.7876(17) -0.127(2) 0.2143(10) 0.043(6) Uiso 1 1 d . . . 
H15B H 0.875(2) -0.201(3) 0.2526(10) 0.061(8) Uiso 1 1 d . . . 
H15C H 0.871(2) -0.046(3) 0.2556(9) 0.055(7) Uiso 1 1 d . . . 
H16A H 0.5542(17) -0.423(2) 0.3326(8) 0.040(6) Uiso 1 1 d . . . 
H16B H 0.4803(16) -0.309(2) 0.3109(9) 0.039(6) Uiso 1 1 d . . . 
H16C H 0.4912(15) -0.3485(19) 0.3791(9) 0.031(5) 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 O1 1.4270(13) . ? 
S1 O2 1.4388(12) . ? 
S1 N1 1.6301(15) . ? 
S1 C5 1.7622(17) . ? 
N1 N2 1.4254(18) . ? 
N2 C8 1.489(2) . ? 
N2 C11 1.492(2) . ? 
C1 C2 1.510(3) . ? 
C2 C3 1.389(3) . ? 
C2 C7 1.394(3) . ? 
C3 C4 1.389(3) . ? 
C4 C5 1.387(2) . ? 
C5 C6 1.387(3) . ? 
C6 C7 1.381(3) . ? 
C8 C14 1.505(3) . ? 
C8 C9 1.531(2) . ? 
C9 C10 1.545(3) . ? 
C10 C11 1.544(2) . ? 
C11 C16 1.507(3) . ? 
C11 C12 1.544(2) . ? 
C12 C13 1.506(3) . ? 
C13 C14 1.328(3) . ? 
C13 C15 1.500(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 
O1 S1 O2 119.85(8) . . ? 
O1 S1 N1 109.00(8) . . ? 
O2 S1 N1 103.74(7) . . ? 
O1 S1 C5 108.01(8) . . ? 
O2 S1 C5 109.35(8) . . ? 
N1 S1 C5 106.06(8) . . ? 
N2 N1 S1 115.11(11) . . ? 
N1 N2 C8 114.40(14) . . ? 
N1 N2 C11 110.07(12) . . ? 
C8 N2 C11 102.94(13) . . ? 
C3 C2 C7 118.55(17) . . ? 
C3 C2 C1 120.64(18) . . ? 
C7 C2 C1 120.80(19) . . ? 
C4 C3 C2 120.97(16) . . ? 
C5 C4 C3 119.48(18) . . ? 
C6 C5 C4 120.28(16) . . ? 
C6 C5 S1 119.21(13) . . ? 
C4 C5 S1 120.10(14) . . ? 
C7 C6 C5 119.66(17) . . ? 
C6 C7 C2 121.02(19) . . ? 
N2 C8 C14 111.57(14) . . ? 
N2 C8 C9 99.84(14) . . ? 
C14 C8 C9 110.92(15) . . ? 
C8 C9 C10 103.24(13) . . ? 
C11 C10 C9 106.16(15) . . ? 
N2 C11 C16 110.82(15) . . ? 
N2 C11 C10 99.68(13) . . ? 
C16 C11 C10 113.47(16) . . ? 
N2 C11 C12 109.30(15) . . ? 
C16 C11 C12 111.52(15) . . ? 
C10 C11 C12 111.42(15) . . ? 
C13 C12 C11 113.84(15) . . ? 
C14 C13 C15 122.7(2) . . ? 
C14 C13 C12 120.44(17) . . ? 
C15 C13 C12 116.89(18) . . ? 
C13 C14 C8 120.58(19) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N1 H1N O2  0.83(2) 2.38(2) 3.167(2) 157.4(19) 2_655 
 
_diffrn_measured_fraction_theta_max    0.990 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.990 
_refine_diff_density_max    0.242 
_refine_diff_density_min   -0.371 
_refine_diff_density_rms    0.050 
