 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H12 S2'
_chemical_formula_weight          292.40
 
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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    11.5930(7)
_cell_length_b                    12.0590(5)
_cell_length_c                    10.7530(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  105.680(2)
_cell_angle_gamma                 90.00
_cell_volume                      1447.33(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unknown
_exptl_crystal_colour             unknown
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           0.1
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              608
_exptl_absorpt_coefficient_mu     0.353
_exptl_absorpt_correction_type    none

 

 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'

_diffrn_reflns_number             5723
_diffrn_reflns_av_R_equivalents   0.0288
_diffrn_reflns_av_sigmaI/netI     0.0429
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.38
_diffrn_reflns_theta_max          26.37
_reflns_number_total              2942
_reflns_number_gt                 2434
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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)+(0.0908P)²+1.5568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2942
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0680
_refine_ls_R_factor_gt            0.0557
_refine_ls_wR_factor_ref          0.1673
_refine_ls_wR_factor_gt           0.1571
_refine_ls_goodness_of_fit_ref    1.063
_refine_ls_restrained_S_all       1.063
_refine_ls_shift/su_max           0.001
_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
S1 S -0.00293(6) 0.12245(6) 0.38634(7) 0.0321(2) Uani 1 1 d . . .
S2 S -0.34755(9) -0.00582(8) 0.40007(9) 0.0474(3) Uani 1 1 d . . .
C11 C -0.3014(2) 0.0866(2) 0.3021(2) 0.0236(5) Uani 1 1 d . . .
C10 C -0.2715(2) 0.0486(2) 0.1841(2) 0.0210(5) Uani 1 1 d . . .
C15 C -0.0813(2) 0.1665(2) 0.2345(2) 0.0221(5) Uani 1 1 d . . .
C8 C -0.3236(2) -0.0603(2) -0.0142(2) 0.0240(5) Uani 1 1 d . . .
C2 C -0.1529(2) 0.0662(2) 0.0301(2) 0.0227(5) Uani 1 1 d . . .
H2 H -0.0898 0.0984 0.0050 0.027 Uiso 1 1 calc R . .
C9 C -0.3434(2) -0.0266(2) 0.1039(3) 0.0240(5) Uani 1 1 d . . .
H9 H -0.4079 -0.0567 0.1283 0.029 Uiso 1 1 calc R . .
C1 C -0.1700(2) 0.0942(2) 0.1478(2) 0.0204(5) Uani 1 1 d . . .
C12 C -0.30200(19) 0.2024(2) 0.3468(2) 0.0208(5) Uani 1 1 d . . .
H12 H -0.2801 0.2656 0.3091 0.025 Uiso 1 1 calc R . .
C16 C -0.0416(2) 0.2721(2) 0.2059(3) 0.0237(5) Uani 1 1 d . . .
H16 H -0.0712 0.3102 0.1287 0.028 Uiso 1 1 calc R . .
C4 C -0.2088(3) -0.0417(3) -0.1745(3) 0.0309(6) Uani 1 1 d . . .
H4 H -0.1476 -0.0088 -0.2021 0.037 Uiso 1 1 calc R . .
C7 C -0.3951(2) -0.1420(2) -0.0948(3) 0.0321(6) Uani 1 1 d . . .
H7 H -0.4573 -0.1759 -0.0697 0.039 Uiso 1 1 calc R . .
C3 C -0.2285(2) -0.0103(2) -0.0545(2) 0.0237(5) Uani 1 1 d . . .
C17 C 0.0513(3) 0.3115(2) 0.3143(3) 0.0332(6) Uani 1 1 d . . .
H17 H 0.0888 0.3797 0.3144 0.040 Uiso 1 1 calc R . .
C18 C 0.0795(2) 0.2412(3) 0.4159(3) 0.0317(6) Uani 1 1 d . . .
H18 H 0.1371 0.2559 0.4930 0.038 Uiso 1 1 calc R . .
C13 C -0.3445(2) 0.1966(3) 0.4638(3) 0.0367(7) Uani 1 1 d . . .
H13 H -0.3536 0.2597 0.5101 0.044 Uiso 1 1 calc R . .
C5 C -0.2802(3) -0.1208(3) -0.2494(3) 0.0359(7) Uani 1 1 d . . .
H5 H -0.2669 -0.1412 -0.3278 0.043 Uiso 1 1 calc R . .
C14 C -0.3695(3) 0.0943(3) 0.4997(3) 0.0444(8) Uani 1 1 d . . .
H14 H -0.3961 0.0806 0.5724 0.053 Uiso 1 1 calc R . .
C6 C -0.3727(3) -0.1709(3) -0.2092(3) 0.0372(7) Uani 1 1 d . . .
H6 H -0.4197 -0.2248 -0.2609 0.045 Uiso 1 1 calc R . .
 
 
_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
S1 C18 1.703(3) . ?
S1 C15 1.724(3) . ?
S2 C14 1.679(4) . ?
S2 C11 1.716(3) . ?
C11 C10 1.475(3) . ?
C11 C12 1.478(4) . ?
C10 C9 1.368(4) . ?
C10 C1 1.445(3) . ?
C15 C16 1.416(4) . ?
C15 C1 1.473(3) . ?
C8 C9 1.411(4) . ?
C8 C7 1.421(4) . ?
C8 C3 1.422(4) . ?
C2 C1 1.375(3) . ?
C2 C3 1.419(4) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C12 C13 1.471(3) . ?
C12 H12 0.9300 . ?
C16 C17 1.436(4) . ?
C16 H16 0.9300 . ?
C4 C5 1.372(4) . ?
C4 C3 1.421(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.370(4) . ?
C7 H7 0.9300 . ?
C17 C18 1.352(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C13 C14 1.347(5) . ?
C13 H13 0.9300 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
 
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
C18 S1 C15 92.50(13) . . ?
C14 S2 C11 92.92(16) . . ?
C10 C11 C12 126.6(2) . . ?
C10 C11 S2 120.8(2) . . ?
C12 C11 S2 112.58(18) . . ?
C9 C10 C1 119.0(2) . . ?
C9 C10 C11 120.2(2) . . ?
C1 C10 C11 120.8(2) . . ?
C16 C15 C1 127.4(2) . . ?
C16 C15 S1 111.31(19) . . ?
C1 C15 S1 121.10(19) . . ?
C9 C8 C7 122.6(2) . . ?
C9 C8 C3 118.7(2) . . ?
C7 C8 C3 118.7(2) . . ?
C1 C2 C3 122.1(2) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C10 C9 C8 122.6(2) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C2 C1 C10 119.1(2) . . ?
C2 C1 C15 118.6(2) . . ?
C10 C1 C15 122.3(2) . . ?
C13 C12 C11 105.4(2) . . ?
C13 C12 H12 127.3 . . ?
C11 C12 H12 127.3 . . ?
C15 C16 C17 109.8(2) . . ?
C15 C16 H16 125.1 . . ?
C17 C16 H16 125.1 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 C8 118.4(2) . . ?
C4 C3 C8 119.4(2) . . ?
C18 C17 C16 114.4(3) . . ?
C18 C17 H17 122.8 . . ?
C16 C17 H17 122.8 . . ?
C17 C18 S1 112.0(2) . . ?
C17 C18 H18 124.0 . . ?
S1 C18 H18 124.0 . . ?
C14 C13 C12 115.9(3) . . ?
C14 C13 H13 122.1 . . ?
C12 C13 H13 122.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C13 C14 S2 113.2(2) . . ?
C13 C14 H14 123.4 . . ?
S2 C14 H14 123.4 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              26.37
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.742
_refine_diff_density_min   -0.486
_refine_diff_density_rms    0.076
