data_99sot062
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H21 N3 O3 S'
_chemical_formula_weight          311.40
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.661(2)
_cell_length_b                    11.852(2)
_cell_length_c                    13.501(3)
_cell_angle_alpha                 76.85(3)
_cell_angle_beta                  81.35(3)
_cell_angle_gamma                 72.12(3)
_cell_volume                      1575.1(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     20603
_cell_measurement_theta_min       1.84
_cell_measurement_theta_max       26.00
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.1
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              664
_exptl_absorpt_coefficient_mu     0.219
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.879
_exptl_absorpt_correction_T_max   0.986
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(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 Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             20603
_diffrn_reflns_av_R_equivalents   0.0465
_diffrn_reflns_av_sigmaI/netI     0.0479
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          1.84
_diffrn_reflns_theta_max          26.00
_reflns_number_total              6191
_reflns_number_gt                 4949
_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     'CAMERON (Watkin, Pearce 1995)'
_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     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.007(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          6191
_refine_ls_number_parameters      388
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0681
_refine_ls_R_factor_gt            0.0522
_refine_ls_wR_factor_ref          0.1652
_refine_ls_wR_factor_gt           0.1532
_refine_ls_goodness_of_fit_ref    1.192
_refine_ls_restrained_S_all       1.192
_refine_ls_shift/su_max           0.038
_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 0.26281(6) 0.26433(5) 0.36041(4) 0.02859(19) Uani 1 1 d . . .
S2 S 0.58596(5) 0.23711(5) 0.77624(5) 0.02896(19) Uani 1 1 d . . .
O1 O 0.04947(14) 0.34602(13) 0.62645(12) 0.0253(4) Uani 1 1 d . . .
O2 O 0.03554(14) 0.38649(14) 0.82005(12) 0.0283(4) Uani 1 1 d . . .
O3 O -0.18714(13) 0.46374(13) 0.82071(11) 0.0252(4) Uani 1 1 d . . .
N1 N 0.32975(14) 0.06836(13) 0.50639(11) 0.0110(3) Uani 1 1 d . . .
H1 H 0.3405 0.0355 0.5694 0.013 Uiso 1 1 calc R . .
N2 N 0.29676(16) 0.23833(15) 0.55714(13) 0.0221(4) Uani 1 1 d . . .
H2 H 0.3213 0.1910 0.6136 0.027 Uiso 1 1 calc R . .
N3 N 0.34790(17) 0.42436(16) 0.51736(14) 0.0262(4) Uani 1 1 d . . .
N4 N 0.38394(14) 0.43715(13) 0.76871(12) 0.0102(3) Uani 1 1 d . . .
H4 H 0.3012 0.4727 0.7802 0.012 Uiso 1 1 calc R . .
N5 N 0.32614(16) 0.26881(15) 0.80970(13) 0.0223(4) Uani 1 1 d . . .
H5 H 0.2470 0.3166 0.8106 0.027 Uiso 1 1 calc R . .
N6 N 0.35824(16) 0.08615(16) 0.75673(14) 0.0239(4) Uani 1 1 d . . .
O5 O 0.08680(15) 0.12372(15) 1.06432(13) 0.0334(4) Uani 1 1 d . . .
O4 O 0.33225(14) 0.15089(13) 1.00732(11) 0.0236(3) Uani 1 1 d . . .
O6 O 0.14635(13) 0.02384(13) 1.22208(11) 0.0257(4) Uani 1 1 d . . .
C1 C 0.29710(19) 0.18897(19) 0.47740(16) 0.0214(5) Uani 1 1 d . . .
C2 C 0.3469(2) -0.00649(19) 0.43122(17) 0.0260(5) Uani 1 1 d . . .
H2A H 0.4274 -0.0055 0.3871 0.031 Uiso 1 1 calc R . .
H2B H 0.2727 0.0232 0.3894 0.031 Uiso 1 1 calc R . .
C3 C 0.3548(2) -0.1320(2) 0.48865(18) 0.0313(5) Uani 1 1 d . . .
H3A H 0.4259 -0.1588 0.5321 0.047 Uiso 1 1 calc R . .
H3B H 0.3705 -0.1852 0.4412 0.047 Uiso 1 1 calc R . .
H3C H 0.2729 -0.1325 0.5294 0.047 Uiso 1 1 calc R . .
C4 C 0.2578(2) 0.36535(19) 0.55358(16) 0.0215(5) Uani 1 1 d . . .
C5 C 0.3117(2) 0.5433(2) 0.51661(17) 0.0269(5) Uani 1 1 d . . .
H5A H 0.3733 0.5861 0.4909 0.032 Uiso 1 1 calc R . .
C6 C 0.1867(2) 0.6051(2) 0.55235(17) 0.0265(5) Uani 1 1 d . . .
H6 H 0.1652 0.6879 0.5501 0.032 Uiso 1 1 calc R . .
C7 C 0.0942(2) 0.54289(19) 0.59142(17) 0.0252(5) Uani 1 1 d . . .
H7 H 0.0101 0.5823 0.6170 0.030 Uiso 1 1 calc R . .
C8 C 0.12995(19) 0.42037(18) 0.59151(16) 0.0211(5) Uani 1 1 d . . .
C9 C -0.0767(2) 0.3969(2) 0.67505(17) 0.0242(5) Uani 1 1 d . . .
H9A H -0.1323 0.3443 0.6798 0.029 Uiso 1 1 calc R . .
H9B H -0.1184 0.4744 0.6340 0.029 Uiso 1 1 calc R . .
C10 C -0.06624(19) 0.41381(18) 0.78026(16) 0.0214(5) Uani 1 1 d . . .
C11 C -0.2066(2) 0.5008(2) 0.92125(18) 0.0302(5) Uani 1 1 d . . .
C12 C -0.1708(3) 0.3882(2) 1.00372(19) 0.0400(6) Uani 1 1 d . . .
H12A H -0.2215 0.3352 0.9999 0.060 Uiso 1 1 calc R . .
H12B H -0.1900 0.4107 1.0695 0.060 Uiso 1 1 calc R . .
H12C H -0.0782 0.3476 0.9939 0.060 Uiso 1 1 calc R . .
C13 C -0.3528(2) 0.5651(3) 0.9304(2) 0.0462(7) Uani 1 1 d . . .
H13A H -0.3741 0.6287 0.8719 0.069 Uiso 1 1 calc R . .
H13B H -0.3748 0.5988 0.9912 0.069 Uiso 1 1 calc R . .
H13C H -0.4022 0.5087 0.9339 0.069 Uiso 1 1 calc R . .
C14 C -0.1275(2) 0.5882(2) 0.9173(2) 0.0344(6) Uani 1 1 d . . .
H14A H -0.0350 0.5455 0.9162 0.052 Uiso 1 1 calc R . .
H14B H -0.1537 0.6250 0.9764 0.052 Uiso 1 1 calc R . .
H14C H -0.1436 0.6497 0.8568 0.052 Uiso 1 1 calc R . .
C15 C 0.4281(2) 0.31670(18) 0.78514(16) 0.0216(5) Uani 1 1 d . . .
C16 C 0.4775(2) 0.50746(19) 0.73122(18) 0.0271(5) Uani 1 1 d . . .
H16A H 0.5099 0.5010 0.6611 0.032 Uiso 1 1 calc R . .
H16B H 0.5523 0.4778 0.7724 0.032 Uiso 1 1 calc R . .
C17 C 0.4067(2) 0.6359(2) 0.7378(2) 0.0325(5) Uani 1 1 d . . .
H17A H 0.3313 0.6635 0.6984 0.049 Uiso 1 1 calc R . .
H17B H 0.4654 0.6851 0.7114 0.049 Uiso 1 1 calc R . .
H17C H 0.3777 0.6417 0.8078 0.049 Uiso 1 1 calc R . .
C18 C 0.34403(19) 0.14224(18) 0.83428(16) 0.0199(4) Uani 1 1 d . . .
C19 C 0.3742(2) -0.03282(19) 0.77709(17) 0.0252(5) Uani 1 1 d . . .
H19 H 0.3857 -0.0728 0.7231 0.030 Uiso 1 1 calc R . .
C20 C 0.3743(2) -0.09857(19) 0.87599(18) 0.0260(5) Uani 1 1 d . . .
H20 H 0.3853 -0.1813 0.8878 0.031 Uiso 1 1 calc R . .
C21 C 0.35806(19) -0.04102(19) 0.95686(17) 0.0238(5) Uani 1 1 d . . .
H21 H 0.3568 -0.0838 1.0237 0.029 Uiso 1 1 calc R . .
C22 C 0.34355(19) 0.08250(19) 0.93638(16) 0.0210(5) Uani 1 1 d . . .
C23 C 0.3043(2) 0.09736(19) 1.11072(16) 0.0227(5) Uani 1 1 d . . .
H23A H 0.3134 0.1472 1.1556 0.027 Uiso 1 1 calc R . .
H23B H 0.3673 0.0184 1.1273 0.027 Uiso 1 1 calc R . .
C24 C 0.1648(2) 0.08448(19) 1.12755(17) 0.0237(5) Uani 1 1 d . . .
C25 C 0.0179(2) -0.0028(2) 1.25785(19) 0.0292(5) Uani 1 1 d . . .
C26 C -0.0071(2) -0.0791(2) 1.1912(2) 0.0363(6) Uani 1 1 d . . .
H26A H -0.0359 -0.0288 1.1275 0.054 Uiso 1 1 calc R . .
H26B H -0.0743 -0.1162 1.2252 0.054 Uiso 1 1 calc R . .
H26C H 0.0731 -0.1406 1.1785 0.054 Uiso 1 1 calc R . .
C27 C -0.0901(2) 0.1157(2) 1.2603(2) 0.0429(7) Uani 1 1 d . . .
H27A H -0.0617 0.1653 1.2943 0.064 Uiso 1 1 calc R . .
H27B H -0.1693 0.0995 1.2964 0.064 Uiso 1 1 calc R . .
H27C H -0.1075 0.1572 1.1917 0.064 Uiso 1 1 calc R . .
C28 C 0.0425(3) -0.0758(3) 1.3651(2) 0.0438(7) Uani 1 1 d . . .
H28A H 0.1218 -0.1415 1.3623 0.066 Uiso 1 1 calc R . .
H28B H -0.0310 -0.1074 1.3929 0.066 Uiso 1 1 calc R . .
H28C H 0.0521 -0.0247 1.4076 0.066 Uiso 1 1 calc R . .
 
 
_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 C1 1.661(2) . ?
S2 C15 1.659(2) . ?
O1 C8 1.374(3) . ?
O1 C9 1.421(2) . ?
O2 C10 1.205(2) . ?
O3 C10 1.333(2) . ?
O3 C11 1.486(3) . ?
N1 C1 1.341(3) . ?
N1 C2 1.451(3) . ?
N2 C1 1.336(3) . ?
N2 C4 1.425(3) . ?
N3 C4 1.329(3) . ?
N3 C5 1.341(3) . ?
N4 C15 1.335(3) . ?
N4 C16 1.453(3) . ?
N5 C15 1.341(3) . ?
N5 C18 1.419(3) . ?
N6 C18 1.330(3) . ?
N6 C19 1.335(3) . ?
O5 C24 1.197(3) . ?
O4 C22 1.359(3) . ?
O4 C23 1.424(3) . ?
O6 C24 1.334(3) . ?
O6 C25 1.485(3) . ?
C2 C3 1.496(3) . ?
C4 C8 1.394(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.383(3) . ?
C9 C10 1.504(3) . ?
C11 C13 1.510(3) . ?
C11 C14 1.512(4) . ?
C11 C12 1.518(3) . ?
C16 C17 1.494(3) . ?
C18 C22 1.399(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.390(3) . ?
C23 C24 1.519(3) . ?
C25 C26 1.513(4) . ?
C25 C28 1.523(4) . ?
C25 C27 1.522(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
C8 O1 C9 117.13(16) . . ?
C10 O3 C11 120.81(16) . . ?
C1 N1 C2 119.84(17) . . ?
C1 N2 C4 123.44(17) . . ?
C4 N3 C5 117.46(19) . . ?
C15 N4 C16 119.16(16) . . ?
C15 N5 C18 122.45(17) . . ?
C18 N6 C19 118.55(19) . . ?
C22 O4 C23 116.34(16) . . ?
C24 O6 C25 119.88(16) . . ?
N2 C1 N1 109.35(18) . . ?
N2 C1 S1 125.64(16) . . ?
N1 C1 S1 125.00(17) . . ?
N1 C2 C3 107.07(18) . . ?
N3 C4 C8 123.4(2) . . ?
N3 C4 N2 117.74(18) . . ?
C8 C4 N2 118.77(18) . . ?
N3 C5 C6 122.9(2) . . ?
C7 C6 C5 119.4(2) . . ?
C6 C7 C8 118.3(2) . . ?
O1 C8 C7 125.50(18) . . ?
O1 C8 C4 115.96(18) . . ?
C7 C8 C4 118.54(19) . . ?
O1 C9 C10 111.66(17) . . ?
O2 C10 O3 126.5(2) . . ?
O2 C10 C9 124.87(19) . . ?
O3 C10 C9 108.66(17) . . ?
O3 C11 C13 102.69(18) . . ?
O3 C11 C14 109.32(19) . . ?
C13 C11 C14 110.0(2) . . ?
O3 C11 C12 108.8(2) . . ?
C13 C11 C12 111.6(2) . . ?
C14 C11 C12 113.8(2) . . ?
N4 C15 N5 110.19(17) . . ?
N4 C15 S2 125.18(16) . . ?
N5 C15 S2 124.63(16) . . ?
N4 C16 C17 107.60(18) . . ?
N6 C18 C22 122.98(19) . . ?
N6 C18 N5 116.93(18) . . ?
C22 C18 N5 120.08(19) . . ?
N6 C19 C20 122.1(2) . . ?
C21 C20 C19 119.8(2) . . ?
C20 C21 C22 118.6(2) . . ?
O4 C22 C21 125.54(19) . . ?
O4 C22 C18 116.41(18) . . ?
C21 C22 C18 118.0(2) . . ?
O4 C23 C24 110.48(17) . . ?
O5 C24 O6 127.2(2) . . ?
O5 C24 C23 123.9(2) . . ?
O6 C24 C23 108.91(17) . . ?
O6 C25 C26 109.58(19) . . ?
O6 C25 C28 102.10(17) . . ?
C26 C25 C28 110.5(2) . . ?
O6 C25 C27 108.87(19) . . ?
C26 C25 C27 113.8(2) . . ?
C28 C25 C27 111.4(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              26.00
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.658
_refine_diff_density_min   -0.915
_refine_diff_density_rms    0.103
