 
data_00tam037
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H9 N3 O2 S2'
_chemical_formula_weight          255.31
 
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                    6.5117(13)
_cell_length_b                    7.9405(16)
_cell_length_c                    11.213(2)
_cell_angle_alpha                 75.67(3)
_cell_angle_beta                  86.60(3)
_cell_angle_gamma                 75.93(3)
_cell_volume                      544.88(19)
_cell_formula_units_Z             2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.46
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.275
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.556
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              264
_exptl_absorpt_coefficient_mu     0.476
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.855
_exptl_absorpt_correction_T_max   0.954
_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             4557
_diffrn_reflns_av_R_equivalents   0.0359
_diffrn_reflns_av_sigmaI/netI     0.0433
_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        -11
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          27.46
_reflns_number_total              2143
_reflns_number_gt                 1822
_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)+(0.0499P)²+0.1374P] 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          2143
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0432
_refine_ls_R_factor_gt            0.0355
_refine_ls_wR_factor_ref          0.1005
_refine_ls_wR_factor_gt           0.0951
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_restrained_S_all       1.069
_refine_ls_shift/su_max           0.000
_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
S12 S 0.14895(8) 0.17301(6) 0.00690(5) 0.03962(17) Uani 1 1 d . . .
S11 S 0.53736(7) 0.10621(6) 0.20365(4) 0.03738(17) Uani 1 1 d . . .
O12 O 0.4406(2) -0.03103(19) 0.18724(14) 0.0479(4) Uani 1 1 d . . .
O11 O 0.7623(2) 0.0654(2) 0.21804(15) 0.0518(4) Uani 1 1 d . . .
N12 N 0.4785(3) 0.2827(2) 0.09109(15) 0.0401(4) Uani 1 1 d . . .
N13 N 0.2774(3) 0.4509(2) -0.07808(16) 0.0402(4) Uani 1 1 d . . .
C14 C 0.4228(3) 0.1792(2) 0.33374(17) 0.0373(4) Uani 1 1 d . . .
N14 N 0.1148(3) 0.4691(2) -0.15712(16) 0.0420(4) Uani 1 1 d . . .
C17 C 0.3221(3) 0.3046(2) 0.01418(17) 0.0339(4) Uani 1 1 d . . .
C19 C 0.0329(3) 0.3327(3) -0.12262(19) 0.0385(4) Uani 1 1 d . . .
C13 C 0.5452(4) 0.2359(3) 0.4047(2) 0.0557(6) Uani 1 1 d . . .
C15 C 0.2149(4) 0.1784(4) 0.3649(2) 0.0571(6) Uani 1 1 d . . .
C20 C -0.1464(4) 0.3094(4) -0.1879(3) 0.0530(6) Uani 1 1 d . . .
C12 C 0.4601(5) 0.2905(4) 0.5084(3) 0.0683(7) Uani 1 1 d . . .
C11 C 0.2538(5) 0.2914(4) 0.5391(3) 0.0676(8) Uani 1 1 d . . .
C16 C 0.1333(5) 0.2362(5) 0.4684(3) 0.0747(9) Uani 1 1 d . . .
H20B H -0.106(4) 0.208(4) -0.224(3) 0.072(8) Uiso 1 1 d . . .
H15 H 0.140(5) 0.133(4) 0.320(3) 0.080(9) Uiso 1 1 d . . .
H17 H 0.341(4) 0.532(3) -0.084(2) 0.055(7) Uiso 1 1 d . . .
H20A H -0.270(5) 0.290(4) -0.135(3) 0.082(9) Uiso 1 1 d . . .
H13 H 0.690(5) 0.231(4) 0.382(3) 0.084(9) Uiso 1 1 d . . .
H12 H 0.554(5) 0.321(5) 0.563(3) 0.104(11) Uiso 1 1 d . . .
H16 H -0.004(6) 0.237(5) 0.488(3) 0.104(11) Uiso 1 1 d . . .
H11 H 0.195(5) 0.332(4) 0.608(3) 0.092(10) Uiso 1 1 d . . .
H20C H -0.190(5) 0.412(5) -0.253(3) 0.085(10) Uiso 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
S12 0.0438(3) 0.0352(3) 0.0431(3) -0.0071(2) 0.0004(2) -0.0178(2)
S11 0.0420(3) 0.0349(3) 0.0359(3) -0.0052(2) 0.0009(2) -0.0139(2)
O12 0.0641(9) 0.0368(8) 0.0469(9) -0.0066(6) -0.0022(7) -0.0226(7)
O11 0.0389(8) 0.0591(10) 0.0543(9) -0.0110(8) 0.0019(6) -0.0091(7)
N12 0.0515(9) 0.0391(9) 0.0331(9) -0.0020(7) -0.0016(7) -0.0236(8)
N13 0.0472(9) 0.0395(9) 0.0375(9) -0.0029(7) -0.0034(7) -0.0228(8)
C14 0.0430(10) 0.0331(10) 0.0318(10) -0.0003(8) -0.0030(8) -0.0086(8)
N14 0.0441(9) 0.0412(9) 0.0416(10) -0.0062(7) -0.0043(7) -0.0144(7)
C17 0.0399(10) 0.0339(9) 0.0304(9) -0.0091(8) 0.0066(7) -0.0136(8)
C19 0.0377(9) 0.0377(10) 0.0406(11) -0.0107(9) 0.0010(8) -0.0090(8)
C13 0.0604(14) 0.0651(15) 0.0498(14) -0.0182(11) -0.0023(11) -0.0252(12)
C15 0.0469(12) 0.0782(18) 0.0465(13) -0.0143(12) 0.0003(10) -0.0159(12)
C20 0.0469(12) 0.0517(14) 0.0633(16) -0.0133(13) -0.0104(11) -0.0151(11)
C12 0.092(2) 0.0684(17) 0.0499(15) -0.0229(13) -0.0069(14) -0.0195(15)
C11 0.087(2) 0.0603(16) 0.0439(14) -0.0131(12) 0.0033(13) 0.0032(14)
C16 0.0529(14) 0.105(2) 0.0581(17) -0.0202(16) 0.0127(12) -0.0052(15)
 
_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
S12 C17 1.7311(19) . ?
S12 C19 1.744(2) . ?
S11 O11 1.4311(15) . ?
S11 O12 1.4372(14) . ?
S11 N12 1.6199(17) . ?
S11 C14 1.761(2) . ?
N12 C17 1.324(3) . ?
N13 C17 1.334(3) . ?
N13 N14 1.378(2) . ?
C14 C13 1.378(3) . ?
C14 C15 1.379(3) . ?
N14 C19 1.286(3) . ?
C19 C20 1.486(3) . ?
C13 C12 1.379(4) . ?
C15 C16 1.383(4) . ?
C12 C11 1.366(4) . ?
C11 C16 1.360(4) . ?
 
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 S12 C19 88.86(9) . . ?
O11 S11 O12 118.75(10) . . ?
O11 S11 N12 106.17(10) . . ?
O12 S11 N12 111.11(9) . . ?
O11 S11 C14 107.42(10) . . ?
O12 S11 C14 108.13(9) . . ?
N12 S11 C14 104.27(9) . . ?
C17 N12 S11 120.90(13) . . ?
C17 N13 N14 118.32(16) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 S11 118.80(17) . . ?
C15 C14 S11 120.74(17) . . ?
C19 N14 N13 109.10(17) . . ?
N12 C17 N13 119.72(17) . . ?
N12 C17 S12 131.85(15) . . ?
N13 C17 S12 108.43(14) . . ?
N14 C19 C20 123.2(2) . . ?
N14 C19 S12 115.29(16) . . ?
C20 C19 S12 121.51(17) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C15 C16 118.3(3) . . ?
C11 C12 C13 120.0(3) . . ?
C16 C11 C12 120.0(3) . . ?
C11 C16 C15 121.4(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.857
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.857
_refine_diff_density_max    0.205
_refine_diff_density_min   -0.350
_refine_diff_density_rms    0.051
