data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H4 N2 S2'
_chemical_formula_weight          240.29
 
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'
 '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                    3.8247(2)
_cell_length_b                    7.8279(4)
_cell_length_c                    17.0839(10)
_cell_angle_alpha                 99.951(3)
_cell_angle_beta                  95.698(3)
_cell_angle_gamma                 94.805(4)
_cell_volume                      498.63(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.600
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              244
_exptl_absorpt_coefficient_mu     0.499
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.9289
_exptl_absorpt_correction_T_max   0.9901
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8790
_diffrn_reflns_av_R_equivalents   0.0598
_diffrn_reflns_av_sigmaI/netI     0.0553
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.44
_diffrn_reflns_theta_max          26.00
_reflns_number_total              1942
_reflns_number_gt                 1517
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_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 w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.1615P] where P=(Fo^2^+2Fc^2^)/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        0.004(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1942
_refine_ls_number_parameters      162
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0609
_refine_ls_R_factor_gt            0.0399
_refine_ls_wR_factor_ref          0.0979
_refine_ls_wR_factor_gt           0.0911
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_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_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.59129(16) 0.39260(7) 0.41013(4) 0.0262(2) Uani 1 d . . .
S2 S 0.48188(16) 0.43704(7) 0.17775(4) 0.0254(2) Uani 1 d . . .
N1 N 1.1898(6) -0.2986(3) 0.33355(14) 0.0337(5) Uani 1 d . . .
N2 N 1.0751(6) -0.2532(3) 0.08192(14) 0.0366(6) Uani 1 d . . .
C1 C 0.7228(7) 0.2277(3) 0.45785(16) 0.0277(6) Uani 1 d . . .
H1 H 0.718(7) 0.231(3) 0.5139(19) 0.042(8) Uiso 1 d . . .
C2 C 0.8124(6) 0.0880(3) 0.40645(15) 0.0248(6) Uani 1 d . . .
H2 H 0.885(6) -0.014(3) 0.4200(14) 0.018(6) Uiso 1 d . . .
C3 C 0.7730(6) 0.1174(3) 0.32648(14) 0.0207(5) Uani 1 d . . .
C4 C 0.6503(6) 0.2770(3) 0.31987(14) 0.0210(5) Uani 1 d . . .
C5 C 0.6116(6) 0.2935(3) 0.23565(14) 0.0207(5) Uani 1 d . . .
C6 C 0.7154(6) 0.1444(3) 0.19042(14) 0.0219(5) Uani 1 d . . .
C7 C 0.6869(6) 0.1496(3) 0.10688(15) 0.0246(5) Uani 1 d . . .
H7 H 0.737(6) 0.058(3) 0.0663(15) 0.022(6) Uiso 1 d . . .
C8 C 0.5648(6) 0.3011(3) 0.09208(16) 0.0272(6) Uani 1 d . . .
H8 H 0.513(7) 0.343(3) 0.0402(17) 0.031(7) Uiso 1 d . . .
C9 C 0.8273(6) 0.0293(3) 0.24589(14) 0.0209(5) Uani 1 d . . .
C10 C 0.9665(6) -0.1251(3) 0.22638(14) 0.0220(5) Uani 1 d . . .
C11 C 1.0852(6) -0.2210(3) 0.28609(15) 0.0256(6) Uani 1 d . . .
C12 C 1.0229(6) -0.1954(3) 0.14550(15) 0.0253(6) Uani 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
S1 0.0315(4) 0.0248(4) 0.0228(4) 0.0019(3) 0.0055(3) 0.0085(3)
S2 0.0290(4) 0.0234(3) 0.0248(4) 0.0064(3) 0.0026(3) 0.0062(3)
N1 0.0435(13) 0.0299(12) 0.0282(13) 0.0046(10) 0.0039(10) 0.0086(10)
N2 0.0472(14) 0.0357(13) 0.0283(14) 0.0044(11) 0.0083(11) 0.0115(11)
C1 0.0326(14) 0.0303(14) 0.0222(15) 0.0063(11) 0.0057(11) 0.0086(11)
C2 0.0287(13) 0.0242(13) 0.0228(14) 0.0059(11) 0.0035(10) 0.0061(11)
C3 0.0198(12) 0.0183(11) 0.0240(14) 0.0031(10) 0.0047(9) 0.0010(9)
C4 0.0200(11) 0.0201(12) 0.0227(13) 0.0022(10) 0.0032(9) 0.0030(10)
C5 0.0195(11) 0.0196(11) 0.0234(13) 0.0050(10) 0.0025(9) 0.0026(9)
C6 0.0202(12) 0.0204(12) 0.0254(14) 0.0049(10) 0.0029(10) 0.0020(10)
C7 0.0242(12) 0.0247(12) 0.0235(14) 0.0011(11) 0.0024(10) 0.0015(10)
C8 0.0290(13) 0.0301(13) 0.0230(14) 0.0059(11) 0.0034(10) 0.0029(11)
C9 0.0180(11) 0.0221(12) 0.0218(13) 0.0032(10) 0.0016(9) 0.0004(10)
C10 0.0244(12) 0.0220(12) 0.0199(13) 0.0034(10) 0.0039(10) 0.0033(10)
C11 0.0279(13) 0.0222(12) 0.0260(15) 0.0000(11) 0.0060(11) 0.0053(11)
C12 0.0261(13) 0.0218(12) 0.0296(16) 0.0069(11) 0.0032(11) 0.0075(10)
 
_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 C4 1.694(2) . ?
S1 C1 1.725(3) . ?
S2 C5 1.693(2) . ?
S2 C8 1.728(3) . ?
N1 C11 1.154(3) . ?
N2 C12 1.146(3) . ?
C1 C2 1.370(3) . ?
C2 C3 1.420(3) . ?
C3 C4 1.389(3) . ?
C3 C9 1.472(3) . ?
C4 C5 1.461(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.428(3) . ?
C6 C9 1.474(3) . ?
C7 C8 1.364(3) . ?
C9 C10 1.364(3) . ?
C10 C11 1.429(3) . ?
C10 C12 1.440(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
C4 S1 C1 91.38(12) . . ?
C5 S2 C8 91.59(12) . . ?
C2 C1 S1 113.1(2) . . ?
C1 C2 C3 110.6(2) . . ?
C4 C3 C2 113.0(2) . . ?
C4 C3 C9 108.0(2) . . ?
C2 C3 C9 139.0(2) . . ?
C3 C4 C5 108.9(2) . . ?
C3 C4 S1 111.86(18) . . ?
C5 C4 S1 139.22(18) . . ?
C6 C5 C4 108.8(2) . . ?
C6 C5 S2 111.84(18) . . ?
C4 C5 S2 139.35(17) . . ?
C5 C6 C7 112.6(2) . . ?
C5 C6 C9 107.8(2) . . ?
C7 C6 C9 139.6(2) . . ?
C8 C7 C6 111.0(2) . . ?
C7 C8 S2 113.0(2) . . ?
C10 C9 C3 127.0(2) . . ?
C10 C9 C6 126.5(2) . . ?
C3 C9 C6 106.49(18) . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 C12 122.2(2) . . ?
C11 C10 C12 116.1(2) . . ?
N1 C11 C10 178.2(3) . . ?
N2 C12 C10 178.2(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              26.00
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.336
_refine_diff_density_min   -0.390
_refine_diff_density_rms    0.109
