 
data_00tam085
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H20 N3 O4 S' 
_chemical_formula_weight          350.41 
 
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                    8.8031(18) 
_cell_length_b                    9.6811(19) 
_cell_length_c                    10.862(2) 
_cell_angle_alpha                 83.99(3) 
_cell_angle_beta                  71.84(3) 
_cell_angle_gamma                 78.35(3) 
_cell_volume                      860.6(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       2.97 
_cell_measurement_theta_max       27.42
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.375
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.25
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.352 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              370 
_exptl_absorpt_coefficient_mu     0.213 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.926 
_exptl_absorpt_correction_T_max   0.948
_exptl_absorpt_process_details    ? 
 
_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'
_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             12927 
_diffrn_reflns_av_R_equivalents   0.0571 
_diffrn_reflns_av_sigmaI/netI     0.0490 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.97 
_diffrn_reflns_theta_max          27.42 
_reflns_number_total              3860 
_reflns_number_gt                 3055 
_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)+(0.0805P)²+0.3013P] 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          3860 
_refine_ls_number_parameters      297 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0644 
_refine_ls_R_factor_gt            0.0476 
_refine_ls_wR_factor_ref          0.1335 
_refine_ls_wR_factor_gt           0.1220 
_refine_ls_goodness_of_fit_ref    0.958 
_refine_ls_restrained_S_all       0.958 
_refine_ls_shift/su_max           0.019 
_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 
S11 S 0.26671(5) 0.25809(5) 0.69096(4) 0.02807(16) Uani 1 1 d . . . 
O11 O 0.21044(15) 0.32868(14) 0.58645(13) 0.0333(3) Uani 1 1 d . . . 
O12 O 0.15590(15) 0.25941(14) 0.81928(13) 0.0352(3) Uani 1 1 d . . . 
O32 O 0.17771(15) 0.54545(15) 0.00929(13) 0.0363(3) Uani 1 1 d . . . 
N12 N 0.33105(19) 0.09392(15) 0.64687(16) 0.0284(3) Uani 1 1 d . . . 
O31 O 0.03556(17) 0.61724(15) -0.13304(15) 0.0426(4) Uani 1 1 d . . . 
N11 N 0.8507(2) 0.46051(19) 0.7017(2) 0.0362(4) Uani 1 1 d . . . 
C35 C 0.0656(2) 0.54489(19) -0.03057(18) 0.0304(4) Uani 1 1 d . . . 
C12 C 0.6960(2) 0.3840(2) 0.58239(18) 0.0319(4) Uani 1 1 d . . . 
C17 C 0.4132(2) -0.01045(18) 0.71618(18) 0.0283(4) Uani 1 1 d . . . 
C16 C 0.5918(2) 0.3941(2) 0.81479(19) 0.0314(4) Uani 1 1 d . . . 
C13 C 0.5585(2) 0.3393(2) 0.57934(18) 0.0316(4) Uani 1 1 d . . . 
C14 C 0.4374(2) 0.32044(18) 0.69460(17) 0.0269(4) Uani 1 1 d . . . 
C15 C 0.4551(2) 0.34732(19) 0.81205(18) 0.0296(4) Uani 1 1 d . . . 
C11 C 0.7152(2) 0.41212(18) 0.70007(18) 0.0287(4) Uani 1 1 d . . . 
C34 C 0.1579(3) 0.7025(3) -0.2087(3) 0.0497(6) Uani 1 1 d . . . 
C32 C -0.0453(3) 0.9287(3) -0.2027(3) 0.0599(7) Uani 1 1 d . . . 
C33 C 0.0753(3) 0.8153(2) -0.2845(2) 0.0451(5) Uani 1 1 d . . . 
C31 C -0.1218(5) 1.0409(4) -0.2866(6) 0.0963(15) Uani 1 1 d . . . 
N13 N 0.52772(19) -0.10459(16) 0.64084(15) 0.0308(4) Uani 1 1 d . . . 
C18 C 0.6069(3) -0.2114(2) 0.7005(2) 0.0374(5) Uani 1 1 d . . . 
C19 C 0.5782(3) -0.2252(2) 0.8324(2) 0.0409(5) Uani 1 1 d . . . 
C21 C 0.3748(3) -0.0172(2) 0.85014(19) 0.0361(4) Uani 1 1 d . . . 
C20 C 0.4601(3) -0.1267(2) 0.9082(2) 0.0408(5) Uani 1 1 d . . . 
H12 H 0.778(3) 0.396(2) 0.505(2) 0.039(6) Uiso 1 1 d . . . 
H13 H 0.549(2) 0.319(2) 0.497(2) 0.033(5) Uiso 1 1 d . . . 
H18 H 0.692(3) -0.276(3) 0.645(2) 0.048(6) Uiso 1 1 d . . . 
H17 H 0.374(2) 0.091(2) 0.565(2) 0.030(5) Uiso 1 1 d . . . 
H16 H 0.607(2) 0.412(2) 0.894(2) 0.032(5) Uiso 1 1 d . . . 
H10 H 0.858(3) 0.463(2) 0.780(2) 0.044(7) Uiso 1 1 d . . . 
H33A H 0.013(3) 0.779(3) -0.340(2) 0.063(8) Uiso 1 1 d . . . 
H20 H 0.431(3) -0.133(2) 1.000(2) 0.041(6) Uiso 1 1 d . . . 
H15 H 0.372(3) 0.336(2) 0.891(2) 0.036(5) Uiso 1 1 d . . . 
H21 H 0.287(3) 0.053(2) 0.898(2) 0.039(6) Uiso 1 1 d . . . 
H19 H 0.638(3) -0.304(3) 0.866(2) 0.049(6) Uiso 1 1 d . . . 
H32B H 0.011(3) 0.962(3) -0.143(2) 0.054(7) Uiso 1 1 d . . . 
H11 H 0.935(3) 0.442(3) 0.637(2) 0.050(7) Uiso 1 1 d . . . 
H34A H 0.168(3) 0.756(3) -0.131(3) 0.064(8) Uiso 1 1 d . . . 
H34B H 0.262(4) 0.638(3) -0.269(3) 0.071(8) Uiso 1 1 d . . . 
H33B H 0.167(3) 0.865(3) -0.354(2) 0.055(7) Uiso 1 1 d . . . 
H32A H -0.125(4) 0.884(3) -0.137(3) 0.069(8) Uiso 1 1 d . . . 
H31C H -0.035(4) 1.081(3) -0.354(3) 0.083(10) Uiso 1 1 d . . . 
H31B H -0.184(6) 1.006(5) -0.325(5) 0.141(19) Uiso 1 1 d . . . 
H31A H -0.198(7) 1.106(6) -0.240(5) 0.17(2) 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 
S11 O12 1.4302(14) . ? 
S11 O11 1.4326(14) . ? 
S11 N12 1.6441(16) . ? 
S11 C14 1.7412(18) . ? 
O32 C35 1.196(2) . ? 
N12 C17 1.413(2) . ? 
O31 C35 1.321(2) . ? 
O31 C34 1.477(3) . ? 
N11 C11 1.373(2) . ? 
C35 C35 1.529(4) 2_565 ? 
C12 C13 1.376(3) . ? 
C12 C11 1.401(3) . ? 
C17 N13 1.337(2) . ? 
C17 C21 1.385(3) . ? 
C16 C15 1.378(3) . ? 
C16 C11 1.396(3) . ? 
C13 C14 1.392(3) . ? 
C14 C15 1.389(3) . ? 
C34 C33 1.504(3) . ? 
C32 C33 1.506(3) . ? 
C32 C31 1.531(5) . ? 
N13 C18 1.351(2) . ? 
C18 C19 1.371(3) . ? 
C19 C20 1.378(3) . ? 
C21 C20 1.386(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 
O12 S11 O11 119.15(8) . . ? 
O12 S11 N12 109.03(9) . . ? 
O11 S11 N12 103.70(8) . . ? 
O12 S11 C14 108.47(9) . . ? 
O11 S11 C14 109.59(8) . . ? 
N12 S11 C14 106.12(8) . . ? 
C17 N12 S11 122.78(13) . . ? 
C35 O31 C34 115.98(16) . . ? 
O32 C35 O31 126.81(18) . . ? 
O32 C35 C35 124.0(2) . 2_565 ? 
O31 C35 C35 109.19(19) . 2_565 ? 
C13 C12 C11 120.83(18) . . ? 
N13 C17 C21 123.16(17) . . ? 
N13 C17 N12 113.79(16) . . ? 
C21 C17 N12 123.02(17) . . ? 
C15 C16 C11 120.41(18) . . ? 
C12 C13 C14 119.70(18) . . ? 
C15 C14 C13 120.05(17) . . ? 
C15 C14 S11 120.33(14) . . ? 
C13 C14 S11 119.60(14) . . ? 
C16 C15 C14 120.19(17) . . ? 
N11 C11 C16 120.78(18) . . ? 
N11 C11 C12 120.38(18) . . ? 
C16 C11 C12 118.81(17) . . ? 
O31 C34 C33 107.20(18) . . ? 
C33 C32 C31 111.1(3) . . ? 
C34 C33 C32 114.1(2) . . ? 
C17 N13 C18 117.29(16) . . ? 
N13 C18 C19 123.4(2) . . ? 
C18 C19 C20 118.38(19) . . ? 
C17 C21 C20 118.12(19) . . ? 
C19 C20 C21 119.6(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.985 
_diffrn_reflns_theta_full              27.42 
_diffrn_measured_fraction_theta_full   0.985 
_refine_diff_density_max    0.427 
_refine_diff_density_min   -0.474 
_refine_diff_density_rms    0.059 
