 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C10 H8 S2'
_chemical_formula_sum
 'C10 H8 S2'
_chemical_formula_weight          192.28
 
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'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pccn
_symmetry_space_group_name_hall   '-P 2ab 2ac'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z'
 'x+1/2, -y, -z+1/2'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z'
 '-x-1/2, y, z-1/2'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    7.4172(4)
_cell_length_b                    21.2420(6)
_cell_length_c                    5.6592(17)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      891.6(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     11814
_cell_measurement_theta_min       3.24
_cell_measurement_theta_max       25.03
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.432
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              400
_exptl_absorpt_coefficient_mu     0.531
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.8787
_exptl_absorpt_correction_T_max   0.9895
_exptl_absorpt_process_details    'SORTAV (R.H. Blessing, 1995, 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 Kappa CCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_decay_%         0
_diffrn_reflns_number             2663
_diffrn_reflns_av_R_equivalents   0.0411
_diffrn_reflns_av_sigmaI/netI     0.0485
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        25
_diffrn_reflns_limit_l_min        -5
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_theta_min          3.84
_diffrn_reflns_theta_max          25.03
_reflns_number_total              775
_reflns_number_gt                 606
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'Cameron'
_computing_publication_material   SHELXL-97
 
_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 > 2σ(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)+(0.0707P)²+0.0781P] 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        0
_refine_ls_number_reflns          775
_refine_ls_number_parameters      71
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0582
_refine_ls_R_factor_gt            0.0423
_refine_ls_wR_factor_ref          0.1205
_refine_ls_wR_factor_gt           0.1115
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_restrained_S_all       1.043
_refine_ls_shift/su_max           0.007
_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
C1 C 0.9279(3) 0.35740(11) 0.0533(4) 0.0249(6) Uani 1 1 d . . .
C2 C 0.9856(3) 0.41567(11) 0.1233(4) 0.0242(6) Uani 1 1 d . . .
C3 C 1.0750(3) 0.41288(12) 0.3472(4) 0.0277(6) Uani 1 1 d . . .
C4 C 1.0842(3) 0.35277(11) 0.4381(4) 0.0239(6) Uani 1 1 d . . .
C5 C 0.9629(3) 0.47189(11) -0.0211(4) 0.0287(6) Uani 1 1 d . . .
S1 S 0.98519(9) 0.29983(3) 0.25179(8) 0.0286(4) Uani 1 1 d . . .
H1 H 0.866(3) 0.3470(9) -0.081(4) 0.021(6) Uiso 1 1 d . . .
H3 H 1.123(4) 0.4520(12) 0.436(5) 0.047(8) Uiso 1 1 d . . .
H4 H 1.123(3) 0.3417(10) 0.567(4) 0.025(7) Uiso 1 1 d . . .
H5 H 0.891(4) 0.4662(12) -0.163(5) 0.052(8) 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
C1 0.0195(13) 0.0300(14) 0.0254(12) -0.0006(11) -0.0004(11) -0.0016(10)
C2 0.0186(13) 0.0264(13) 0.0277(13) -0.0019(12) 0.0010(9) 0.0022(9)
C3 0.0259(14) 0.0293(14) 0.0279(14) -0.0031(11) -0.0013(11) -0.0003(11)
C4 0.0197(13) 0.0319(14) 0.0202(12) -0.0007(11) -0.0016(11) 0.0024(10)
C5 0.0224(14) 0.0350(14) 0.0287(15) -0.0003(12) -0.0012(10) 0.0021(11)
S1 0.0295(5) 0.0247(5) 0.0315(6) 0.0007(2) 0.0009(3) -0.0019(2)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.368(3) . ?
C1 S1 1.714(2) . ?
C1 H1 0.91(2) . ?
C2 C3 1.432(4) . ?
C2 C5 1.457(3) . ?
C3 C4 1.378(3) . ?
C3 H3 1.03(3) . ?
C4 S1 1.708(2) . ?
C4 H4 0.82(2) . ?
C5 C5 1.337(5) 5_765 ?
C5 H5 0.97(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
C2 C1 S1 112.22(19) . . ?
C2 C1 H1 128.0(13) . . ?
S1 C1 H1 119.8(13) . . ?
C1 C2 C3 111.3(2) . . ?
C1 C2 C5 122.9(2) . . ?
C3 C2 C5 125.7(2) . . ?
C4 C3 C2 113.1(2) . . ?
C4 C3 H3 123.1(14) . . ?
C2 C3 H3 123.7(14) . . ?
C3 C4 S1 110.99(18) . . ?
C3 C4 H4 128.1(16) . . ?
S1 C4 H4 120.8(16) . . ?
C5 C5 C2 125.8(3) 5_765 . ?
C5 C5 H5 119.0(16) 5_765 . ?
C2 C5 H5 115.2(16) . . ?
C4 S1 C1 92.38(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.982
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.982
_refine_diff_density_max    0.440
_refine_diff_density_min   -0.372
_refine_diff_density_rms    0.068
