 
data_00tam079
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C10 H11 N3 O2 S2' 
_chemical_formula_weight          269.34 
 
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                    6.2197(12) 
_cell_length_b                    8.1201(16) 
_cell_length_c                    12.208(2) 
_cell_angle_alpha                 103.18(3) 
_cell_angle_beta                  91.76(3) 
_cell_angle_gamma                 104.15(3) 
_cell_volume                      579.7(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature    150(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       3.39
_cell_measurement_theta_max       27.44
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.75
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.543 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              280 
_exptl_absorpt_coefficient_mu     0.452 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.873
_exptl_absorpt_correction_T_max   0.978
_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             8358 
_diffrn_reflns_av_R_equivalents   0.0574 
_diffrn_reflns_av_sigmaI/netI     0.0536 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.39 
_diffrn_reflns_theta_max          27.44 
_reflns_number_total              2576 
_reflns_number_gt                 2023 
_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)+(0.0754P)²+1.4334P] 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        0.006(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2576 
_refine_ls_number_parameters      199 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0540 
_refine_ls_R_factor_gt            0.0369 
_refine_ls_wR_factor_ref          0.1054 
_refine_ls_wR_factor_gt           0.0908 
_refine_ls_goodness_of_fit_ref    0.669 
_refine_ls_restrained_S_all       0.669 
_refine_ls_shift/su_max           0.028 
_refine_ls_shift/su_mean          0.003 
 
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 
N13 N -0.2453(3) 0.5411(2) -0.07354(15) 0.0231(4) Uani 1 1 d . . . 
N14 N -0.4229(3) 0.5217(3) -0.14972(16) 0.0242(4) Uani 1 1 d . . . 
C18 C -0.4999(4) 0.6574(3) -0.12302(19) 0.0229(5) Uani 1 1 d . . . 
C19 C -0.6926(4) 0.6796(4) -0.1880(2) 0.0294(5) Uani 1 1 d . . . 
H13 H 0.233(5) 0.730(4) 0.335(2) 0.035(7) Uiso 1 1 d . . . 
H17 H -0.167(5) 0.456(4) -0.081(3) 0.049(9) Uiso 1 1 d . . . 
H15 H -0.317(5) 0.911(4) 0.300(2) 0.038(8) Uiso 1 1 d . . . 
H16 H -0.437(5) 0.835(4) 0.468(2) 0.040(8) Uiso 1 1 d . . . 
H19C H -0.742(5) 0.577(4) -0.249(3) 0.037(8) Uiso 1 1 d . . . 
H12 H 0.105(5) 0.649(4) 0.503(2) 0.039(8) Uiso 1 1 d . . . 
H19B H -0.657(5) 0.781(4) -0.216(2) 0.040(8) Uiso 1 1 d . . . 
H10A H -0.340(5) 0.760(4) 0.638(3) 0.045(9) Uiso 1 1 d . . . 
H19A H -0.812(6) 0.691(4) -0.145(3) 0.051(9) Uiso 1 1 d . . . 
H10C H -0.350(6) 0.562(5) 0.591(3) 0.055(10) Uiso 1 1 d . . . 
H10B H -0.134(7) 0.687(5) 0.663(3) 0.082(13) Uiso 1 1 d . . . 
S11 S 0.06459(9) 0.88882(7) 0.18275(4) 0.02174(17) Uani 1 1 d . . . 
S12 S -0.36202(9) 0.81827(7) -0.00481(5) 0.02272(17) Uani 1 1 d . . . 
O11 O 0.3031(3) 0.9320(2) 0.19831(14) 0.0278(4) Uani 1 1 d . . . 
O12 O -0.0423(3) 1.0194(2) 0.16351(14) 0.0271(4) Uani 1 1 d . . . 
N12 N -0.0100(3) 0.7129(2) 0.08182(15) 0.0229(4) Uani 1 1 d . . . 
C17 C -0.1841(4) 0.6883(3) 0.00875(17) 0.0197(4) Uani 1 1 d . . . 
C14 C -0.0342(4) 0.8250(3) 0.30417(18) 0.0215(4) Uani 1 1 d . . . 
C12 C 0.0203(4) 0.7041(3) 0.4606(2) 0.0289(5) Uani 1 1 d . . . 
C16 C -0.3018(4) 0.8076(3) 0.4397(2) 0.0311(5) Uani 1 1 d . . . 
C15 C -0.2327(4) 0.8548(3) 0.3417(2) 0.0284(5) Uani 1 1 d . . . 
C13 C 0.0924(4) 0.7492(3) 0.3630(2) 0.0262(5) Uani 1 1 d . . . 
C11 C -0.1779(4) 0.7319(3) 0.50061(19) 0.0283(5) Uani 1 1 d . . . 
C10 C -0.2583(5) 0.6801(4) 0.6060(2) 0.0377(6) Uani 1 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
N13 0.0280(11) 0.0234(10) 0.0213(9) 0.0057(7) 0.0034(7) 0.0126(8) 
N14 0.0243(10) 0.0269(10) 0.0235(10) 0.0076(8) 0.0023(7) 0.0089(8) 
C18 0.0216(11) 0.0237(11) 0.0266(11) 0.0112(9) 0.0077(8) 0.0062(9) 
C19 0.0234(13) 0.0302(13) 0.0367(14) 0.0097(11) 0.0007(10) 0.0095(10) 
S11 0.0235(3) 0.0200(3) 0.0236(3) 0.0057(2) 0.0036(2) 0.0086(2) 
S12 0.0236(3) 0.0207(3) 0.0275(3) 0.0072(2) 0.0047(2) 0.0109(2) 
O11 0.0219(9) 0.0300(9) 0.0334(9) 0.0105(7) 0.0054(6) 0.0075(7) 
O12 0.0324(9) 0.0215(8) 0.0302(9) 0.0059(7) 0.0023(7) 0.0123(7) 
N12 0.0284(10) 0.0228(9) 0.0205(9) 0.0037(7) 0.0012(7) 0.0137(8) 
C17 0.0242(11) 0.0191(10) 0.0207(10) 0.0100(8) 0.0099(8) 0.0094(8) 
C14 0.0213(11) 0.0185(10) 0.0218(10) 0.0010(8) 0.0008(8) 0.0037(8) 
C12 0.0307(13) 0.0307(13) 0.0250(12) 0.0079(10) -0.0008(9) 0.0067(10) 
C16 0.0230(13) 0.0345(13) 0.0324(13) 0.0021(10) 0.0068(9) 0.0064(10) 
C15 0.0271(13) 0.0297(12) 0.0283(12) 0.0032(10) 0.0032(9) 0.0109(10) 
C13 0.0238(12) 0.0275(12) 0.0273(12) 0.0064(9) 0.0018(9) 0.0068(9) 
C11 0.0306(13) 0.0259(12) 0.0202(11) -0.0020(9) 0.0015(9) -0.0007(9) 
C10 0.0442(17) 0.0401(16) 0.0237(13) 0.0041(11) 0.0091(11) 0.0042(13) 
 
_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 
N13 C17 1.338(3) . ? 
N13 N14 1.377(3) . ? 
N14 C18 1.286(3) . ? 
C18 C19 1.487(3) . ? 
C18 S12 1.744(2) . ? 
S11 O11 1.4345(17) . ? 
S11 O12 1.4389(16) . ? 
S11 N12 1.616(2) . ? 
S11 C14 1.759(2) . ? 
S12 C17 1.734(2) . ? 
N12 C17 1.327(3) . ? 
C14 C15 1.387(3) . ? 
C14 C13 1.385(3) . ? 
C12 C13 1.381(3) . ? 
C12 C11 1.390(4) . ? 
C16 C15 1.386(4) . ? 
C16 C11 1.389(4) . ? 
C11 C10 1.506(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 
C17 N13 N14 118.23(18) . . ? 
C18 N14 N13 108.92(19) . . ? 
N14 C18 C19 123.1(2) . . ? 
N14 C18 S12 115.74(18) . . ? 
C19 C18 S12 121.15(18) . . ? 
O11 S11 O12 118.97(10) . . ? 
O11 S11 N12 106.17(10) . . ? 
O12 S11 N12 111.07(10) . . ? 
O11 S11 C14 106.83(10) . . ? 
O12 S11 C14 107.82(10) . . ? 
N12 S11 C14 105.09(10) . . ? 
C17 S12 C18 88.52(11) . . ? 
C17 N12 S11 120.41(15) . . ? 
N12 C17 N13 119.69(19) . . ? 
N12 C17 S12 131.73(17) . . ? 
N13 C17 S12 108.57(16) . . ? 
C15 C14 C13 120.8(2) . . ? 
C15 C14 S11 120.27(18) . . ? 
C13 C14 S11 118.92(18) . . ? 
C13 C12 C11 121.3(2) . . ? 
C15 C16 C11 121.8(2) . . ? 
C14 C15 C16 118.6(2) . . ? 
C12 C13 C14 119.4(2) . . ? 
C16 C11 C12 118.0(2) . . ? 
C16 C11 C10 120.7(2) . . ? 
C12 C11 C10 121.3(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.975 
_diffrn_reflns_theta_full              27.44 
_diffrn_measured_fraction_theta_full   0.975 
_refine_diff_density_max    0.379 
_refine_diff_density_min   -0.445 
_refine_diff_density_rms    0.066 
