 
data_00tam043
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H14 N2 O2 S'
_chemical_formula_weight          262.32
 
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    P21/n
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.778(2)
_cell_length_b                    15.436(3)
_cell_length_c                    15.688(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.46(3)
_cell_angle_gamma                 90.00
_cell_volume                      2548.6(9)
_cell_formula_units_Z             8
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       2.96
_cell_measurement_theta_max       27.37
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.367
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1104
_exptl_absorpt_coefficient_mu     0.249
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.956
_exptl_absorpt_correction_T_max   0.993
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD'
_diffrn_measurement_method        'φ and 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             24439
_diffrn_reflns_av_R_equivalents   0.1853
_diffrn_reflns_av_sigmaI/netI     0.2045
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.37
_reflns_number_total              5279
_reflns_number_gt                 2172
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection      
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0332P)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      SHELXL
_refine_ls_extinction_coef        0.0009(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5279
_refine_ls_number_parameters      438
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2038
_refine_ls_R_factor_gt            0.0570
_refine_ls_wR_factor_ref          0.1342
_refine_ls_wR_factor_gt           0.0976
_refine_ls_goodness_of_fit_ref    0.911
_refine_ls_restrained_S_all       0.911
_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
H13 H 0.680(3) 0.011(2) 0.6461(19) 0.034(10) Uiso 1 1 d . . .
H17 H 1.000(3) 0.124(2) 0.606(2) 0.037(10) Uiso 1 1 d . . .
H14 H 0.658(3) 0.124(2) 0.745(2) 0.054(11) Uiso 1 1 d . . .
H36 H 0.566(3) 0.060(2) 0.316(2) 0.043(11) Uiso 1 1 d . . .
H34 H 0.815(3) -0.088(2) 0.228(2) 0.033(10) Uiso 1 1 d . . .
H19 H 0.474(3) 0.517(2) 0.6045(19) 0.032(9) Uiso 1 1 d . . .
H39 H 1.093(3) 0.280(2) 0.449(2) 0.041(10) Uiso 1 1 d . . .
H22 H 0.869(3) 0.389(2) 0.689(2) 0.038(11) Uiso 1 1 d . . .
H33 H 0.763(3) -0.207(2) 0.302(2) 0.037(10) Uiso 1 1 d . . .
H37 H 0.519(3) -0.053(2) 0.401(2) 0.038(10) Uiso 1 1 d . . .
H37N H 1.062(3) 0.192(2) 0.339(2) 0.057(12) Uiso 1 1 d . . .
H42 H 0.678(3) 0.190(2) 0.340(2) 0.054(12) Uiso 1 1 d . . .
H20 H 0.649(3) 0.566(2) 0.5474(19) 0.022(9) Uiso 1 1 d . . .
H17N H 0.514(3) 0.412(2) 0.703(2) 0.036(10) Uiso 1 1 d . . .
H11B H 0.947(4) -0.028(3) 0.560(2) 0.071(14) Uiso 1 1 d . . .
H11A H 0.842(4) 0.009(3) 0.499(3) 0.066(17) Uiso 1 1 d . . .
H40 H 0.931(3) 0.325(2) 0.524(2) 0.040(10) Uiso 1 1 d . . .
H16 H 0.989(4) 0.235(3) 0.710(2) 0.074(14) Uiso 1 1 d . . .
H11C H 0.799(5) -0.047(3) 0.554(3) 0.10(2) Uiso 1 1 d . . .
H43C H 0.677(4) 0.339(3) 0.486(3) 0.075(17) Uiso 1 1 d . . .
H43B H 0.603(5) 0.255(3) 0.454(3) 0.098(19) Uiso 1 1 d . . .
H43A H 0.694(4) 0.253(3) 0.539(3) 0.071(16) Uiso 1 1 d . . .
H23B H 0.961(3) 0.474(2) 0.595(2) 0.052(12) Uiso 1 1 d . . .
H23C H 0.915(4) 0.573(3) 0.604(3) 0.090(17) Uiso 1 1 d . . .
H23A H 0.872(4) 0.520(3) 0.522(3) 0.09(2) Uiso 1 1 d . . .
H31C H 0.599(4) -0.204(3) 0.469(3) 0.081(17) Uiso 1 1 d . . .
H31A H 0.661(4) -0.268(3) 0.422(3) 0.090(18) Uiso 1 1 d . . .
H31B H 0.517(5) -0.245(3) 0.388(3) 0.13(2) Uiso 1 1 d . . .
S31 S 0.73740(9) 0.08239(7) 0.20094(6) 0.0421(3) Uani 1 1 d . . .
S11 S 0.80441(9) 0.26900(7) 0.81308(7) 0.0436(3) Uani 1 1 d . . .
O12 O 0.9216(2) 0.31718(16) 0.83425(16) 0.0473(7) Uani 1 1 d . . .
O11 O 0.7656(2) 0.22354(16) 0.88346(16) 0.0449(7) Uani 1 1 d . . .
O31 O 0.7748(2) 0.04458(17) 0.12626(15) 0.0466(7) Uani 1 1 d . . .
O32 O 0.6305(2) 0.14091(16) 0.18410(16) 0.0454(7) Uani 1 1 d . . .
N13 N 0.5767(3) 0.4287(2) 0.6782(2) 0.0395(8) Uani 1 1 d . . .
N12 N 0.6838(3) 0.3267(2) 0.77014(19) 0.0395(8) Uani 1 1 d . . .
N32 N 0.8657(3) 0.1252(2) 0.2563(2) 0.0401(8) Uani 1 1 d . . .
C18 C 0.6897(3) 0.3882(3) 0.7086(2) 0.0367(10) Uani 1 1 d . . .
C38 C 0.8658(3) 0.1768(2) 0.3261(3) 0.0384(10) Uani 1 1 d . . .
N33 N 0.9834(3) 0.2084(2) 0.3626(2) 0.0409(9) Uani 1 1 d . . .
C22 C 0.7918(4) 0.4150(3) 0.6740(2) 0.0388(10) Uani 1 1 d . . .
C12 C 0.8446(4) 0.0597(3) 0.6155(3) 0.0456(11) Uani 1 1 d . . .
C14 C 0.7312(4) 0.1241(3) 0.7169(3) 0.0437(11) Uani 1 1 d . . .
C20 C 0.6609(4) 0.5202(3) 0.5863(3) 0.0414(10) Uani 1 1 d . . .
C34 C 0.7557(4) -0.0840(3) 0.2615(3) 0.0486(11) Uani 1 1 d . . .
C35 C 0.6982(3) -0.0043(3) 0.2638(2) 0.0387(10) Uani 1 1 d . . .
C21 C 0.7796(3) 0.4807(3) 0.6135(2) 0.0388(10) Uani 1 1 d . . .
C15 C 0.8207(3) 0.1898(3) 0.7345(2) 0.0396(10) Uani 1 1 d . . .
C37 C 0.5847(4) -0.0629(3) 0.3664(3) 0.0461(11) Uani 1 1 d . . .
C32 C 0.6399(4) -0.1428(3) 0.3626(3) 0.0459(11) Uani 1 1 d . . .
C42 C 0.7666(4) 0.2022(3) 0.3658(3) 0.0416(11) Uani 1 1 d . . .
C16 C 0.9223(4) 0.1917(3) 0.6934(3) 0.0458(11) Uani 1 1 d . . .
C36 C 0.6107(4) 0.0059(3) 0.3165(3) 0.0442(11) Uani 1 1 d . . .
C41 C 0.7880(3) 0.2532(3) 0.4395(3) 0.0450(11) Uani 1 1 d . . .
C31 C 0.6047(6) -0.2191(4) 0.4128(4) 0.0615(14) Uani 1 1 d . . .
C13 C 0.7450(4) 0.0596(3) 0.6583(3) 0.0469(11) Uani 1 1 d . . .
C40 C 0.9117(4) 0.2818(3) 0.4746(3) 0.0476(11) Uani 1 1 d . . .
C17 C 0.9316(4) 0.1269(3) 0.6336(3) 0.0515(12) Uani 1 1 d . . .
C19 C 0.5613(4) 0.4933(3) 0.6185(3) 0.0418(10) Uani 1 1 d . . .
C43 C 0.6795(5) 0.2781(5) 0.4811(4) 0.0625(15) Uani 1 1 d . . .
C39 C 1.0071(4) 0.2593(3) 0.4350(3) 0.0449(11) Uani 1 1 d . . .
C23 C 0.8921(4) 0.5125(4) 0.5797(4) 0.0512(13) Uani 1 1 d . . .
C33 C 0.7266(4) -0.1524(3) 0.3104(3) 0.0493(12) Uani 1 1 d . . .
C11 C 0.8584(6) -0.0113(4) 0.5522(4) 0.0631(15) 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
S31 O31 1.442(2) . ?
S31 O32 1.443(2) . ?
S31 N32 1.608(3) . ?
S31 C35 1.766(4) . ?
S11 O12 1.441(3) . ?
S11 O11 1.444(2) . ?
S11 N12 1.600(3) . ?
S11 C15 1.772(4) . ?
N13 C19 1.355(5) . ?
N13 C18 1.361(4) . ?
N12 C18 1.366(4) . ?
N32 C38 1.353(4) . ?
C18 C22 1.391(5) . ?
C38 N33 1.364(4) . ?
C38 C42 1.404(5) . ?
N33 C39 1.359(5) . ?
C22 C21 1.375(5) . ?
C12 C13 1.384(5) . ?
C12 C17 1.386(5) . ?
C12 C11 1.508(6) . ?
C14 C13 1.386(5) . ?
C14 C15 1.386(5) . ?
C20 C19 1.346(5) . ?
C20 C21 1.398(5) . ?
C34 C33 1.380(6) . ?
C34 C35 1.382(5) . ?
C35 C36 1.391(5) . ?
C21 C23 1.507(5) . ?
C15 C16 1.386(5) . ?
C37 C32 1.375(5) . ?
C37 C36 1.384(5) . ?
C32 C33 1.378(5) . ?
C32 C31 1.510(6) . ?
C42 C41 1.376(5) . ?
C16 C17 1.389(6) . ?
C41 C40 1.400(5) . ?
C41 C43 1.507(6) . ?
C40 C39 1.356(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
O31 S31 O32 117.18(16) . . ?
O31 S31 N32 104.29(15) . . ?
O32 S31 N32 113.65(17) . . ?
O31 S31 C35 106.83(17) . . ?
O32 S31 C35 107.39(17) . . ?
N32 S31 C35 106.90(16) . . ?
O12 S11 O11 117.28(16) . . ?
O12 S11 N12 113.71(16) . . ?
O11 S11 N12 104.43(15) . . ?
O12 S11 C15 107.66(17) . . ?
O11 S11 C15 106.56(17) . . ?
N12 S11 C15 106.52(17) . . ?
C19 N13 C18 123.1(3) . . ?
C18 N12 S11 121.8(2) . . ?
C38 N32 S31 122.0(2) . . ?
N13 C18 N12 113.1(3) . . ?
N13 C18 C22 116.8(4) . . ?
N12 C18 C22 130.2(3) . . ?
N32 C38 N33 112.9(3) . . ?
N32 C38 C42 130.9(4) . . ?
N33 C38 C42 116.2(4) . . ?
C39 N33 C38 123.2(3) . . ?
C21 C22 C18 121.5(4) . . ?
C13 C12 C17 117.7(4) . . ?
C13 C12 C11 120.9(4) . . ?
C17 C12 C11 121.4(4) . . ?
C13 C14 C15 119.2(4) . . ?
C19 C20 C21 120.1(4) . . ?
C33 C34 C35 120.7(4) . . ?
C34 C35 C36 118.8(4) . . ?
C34 C35 S31 119.9(3) . . ?
C36 C35 S31 121.4(3) . . ?
C22 C21 C20 118.5(4) . . ?
C22 C21 C23 121.2(4) . . ?
C20 C21 C23 120.2(4) . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 S11 121.1(3) . . ?
C14 C15 S11 118.3(3) . . ?
C32 C37 C36 121.4(4) . . ?
C37 C32 C33 118.5(4) . . ?
C37 C32 C31 121.2(4) . . ?
C33 C32 C31 120.3(4) . . ?
C41 C42 C38 121.8(4) . . ?
C15 C16 C17 118.6(4) . . ?
C37 C36 C35 119.7(4) . . ?
C42 C41 C40 118.9(4) . . ?
C42 C41 C43 120.3(4) . . ?
C40 C41 C43 120.8(4) . . ?
C12 C13 C14 121.7(4) . . ?
C39 C40 C41 119.4(4) . . ?
C12 C17 C16 122.1(4) . . ?
C20 C19 N13 119.9(4) . . ?
C40 C39 N33 120.4(4) . . ?
C32 C33 C34 120.8(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.913
_diffrn_reflns_theta_full              27.37
_diffrn_measured_fraction_theta_full   0.913
_refine_diff_density_max    0.262
_refine_diff_density_min   -0.272
_refine_diff_density_rms    0.059
