data_2008src0227
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H12 S3'
_chemical_formula_weight          372.50
 
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
 
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                    15.8475(14)
_cell_length_b                    15.8514(14)
_cell_length_c                    6.9724(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.498(6)
_cell_angle_gamma                 90.00
_cell_volume                      1732.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     31436
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              768
_exptl_absorpt_coefficient_mu     0.429
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8305
_exptl_absorpt_correction_T_max   0.9957
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             19708
_diffrn_reflns_av_R_equivalents   0.1068
_diffrn_reflns_av_sigmaI/netI     0.1097
_diffrn_reflns_limit_h_min        -20
_diffrn_reflns_limit_h_max        20
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.22
_diffrn_reflns_theta_max          27.49
_reflns_number_total              3940
_reflns_number_gt                 2605
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_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     'PLATON (Spek, 2003)'
_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)+(0.0995P)²+11.8093P] 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      SHELXL
_refine_ls_extinction_coef        0.013(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3940
_refine_ls_number_parameters      227
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1583
_refine_ls_R_factor_gt            0.1079
_refine_ls_wR_factor_ref          0.2819
_refine_ls_wR_factor_gt           0.2576
_refine_ls_goodness_of_fit_ref    1.104
_refine_ls_restrained_S_all       1.104
_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
C1 C 0.2012(4) 0.3217(4) 0.1690(8) 0.0203(12) Uani 1 1 d . . .
C2 C 0.2335(4) 0.2405(3) 0.1814(8) 0.0188(12) Uani 1 1 d . . .
C3 C 0.3237(4) 0.2380(4) 0.2023(9) 0.0204(12) Uani 1 1 d . . .
C4 C 0.3583(4) 0.3185(4) 0.2103(9) 0.0217(13) Uani 1 1 d . . .
C5 C 0.4536(4) 0.3180(4) 0.2340(9) 0.0235(13) Uani 1 1 d . . .
H5A H 0.4790 0.3465 0.3553 0.028 Uiso 1 1 calc R . .
H5B H 0.4750 0.3449 0.1224 0.028 Uiso 1 1 calc R . .
C6 C 0.4713(4) 0.2235(4) 0.2417(9) 0.0252(14) Uani 1 1 d . . .
C7 C 0.5490(4) 0.1813(4) 0.2653(9) 0.0295(15) Uani 1 1 d . . .
H7 H 0.6011 0.2117 0.2785 0.035 Uiso 1 1 calc R . .
C8 C 0.5488(5) 0.0934(5) 0.2692(10) 0.0344(17) Uani 1 1 d . . .
H8 H 0.6014 0.0637 0.2861 0.041 Uiso 1 1 calc R . .
C9 C 0.4714(5) 0.0479(4) 0.2485(11) 0.0357(17) Uani 1 1 d . . .
H9 H 0.4727 -0.0120 0.2499 0.043 Uiso 1 1 calc R . .
C10 C 0.3936(5) 0.0895(4) 0.2261(9) 0.0270(14) Uani 1 1 d . . .
H10 H 0.3417 0.0588 0.2142 0.032 Uiso 1 1 calc R . .
C11 C 0.3935(4) 0.1777(4) 0.2214(8) 0.0216(13) Uani 1 1 d . . .
C12 C 0.1108(4) 0.3242(4) 0.1450(8) 0.0195(12) Uani 1 1 d . . .
C13 C 0.0763(4) 0.2439(4) 0.1378(8) 0.0197(13) Uani 1 1 d . . .
C14 C -0.0149(4) 0.2451(4) 0.1074(8) 0.0202(13) Uani 1 1 d . . .
C15 C -0.0456(4) 0.3260(4) 0.0981(9) 0.0227(13) Uani 1 1 d . . .
C16 C -0.1423(4) 0.3291(4) 0.0653(9) 0.0256(14) Uani 1 1 d . . .
H16A H -0.1647 0.3569 -0.0589 0.031 Uiso 1 1 calc R . .
H16B H -0.1648 0.3581 0.1729 0.031 Uiso 1 1 calc R . .
C17 C -0.1625(4) 0.2353(4) 0.0609(8) 0.0217(13) Uani 1 1 d . . .
C18 C -0.2418(4) 0.1973(4) 0.0378(9) 0.0267(14) Uani 1 1 d . . .
H18 H -0.2925 0.2302 0.0250 0.032 Uiso 1 1 calc R . .
C19 C -0.2455(5) 0.1087(4) 0.0338(10) 0.0307(15) Uani 1 1 d . . .
H19 H -0.2994 0.0813 0.0147 0.037 Uiso 1 1 calc R . .
C20 C -0.1712(5) 0.0605(4) 0.0575(9) 0.0274(14) Uani 1 1 d . . .
H20 H -0.1750 0.0006 0.0572 0.033 Uiso 1 1 calc R . .
C21 C -0.0909(4) 0.0992(4) 0.0819(9) 0.0258(14) Uani 1 1 d . . .
H21 H -0.0402 0.0663 0.0971 0.031 Uiso 1 1 calc R . .
C22 C -0.0869(4) 0.1873(4) 0.0833(9) 0.0224(13) Uani 1 1 d . . .
S1 S 0.28189(11) 0.39734(9) 0.1875(2) 0.0246(4) Uani 1 1 d . . .
S2 S 0.15308(10) 0.16467(9) 0.1599(2) 0.0205(4) Uani 1 1 d . . .
S3 S 0.03317(10) 0.40211(9) 0.1195(2) 0.0236(4) Uani 1 1 d . . .
 
 
_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
C1 C2 1.383(8) . ?
C1 C12 1.417(8) . ?
C1 S1 1.745(6) . ?
C2 C3 1.415(9) . ?
C2 S2 1.743(6) . ?
C3 C4 1.387(8) . ?
C3 C11 1.454(8) . ?
C4 C5 1.495(9) . ?
C4 S1 1.731(6) . ?
C5 C6 1.524(9) . ?
C6 C7 1.389(9) . ?
C6 C11 1.421(9) . ?
C7 C8 1.393(10) . ?
C8 C9 1.411(11) . ?
C9 C10 1.386(10) . ?
C10 C11 1.398(9) . ?
C12 C13 1.384(8) . ?
C12 S3 1.734(6) . ?
C13 C14 1.429(9) . ?
C13 S2 1.740(6) . ?
C14 C15 1.369(8) . ?
C14 C22 1.454(9) . ?
C15 C16 1.516(9) . ?
C15 S3 1.726(6) . ?
C16 C17 1.520(8) . ?
C17 C18 1.382(9) . ?
C17 C22 1.410(9) . ?
C18 C19 1.407(9) . ?
C19 C20 1.393(10) . ?
C20 C21 1.400(9) . ?
C21 C22 1.397(9) . ?
 
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 C12 113.2(5) . . ?
C2 C1 S1 112.0(5) . . ?
C12 C1 S1 134.9(5) . . ?
C1 C2 C3 113.1(5) . . ?
C1 C2 S2 112.1(5) . . ?
C3 C2 S2 134.8(5) . . ?
C4 C3 C2 111.5(5) . . ?
C4 C3 C11 108.1(5) . . ?
C2 C3 C11 140.4(6) . . ?
C3 C4 C5 112.8(5) . . ?
C3 C4 S1 113.1(5) . . ?
C5 C4 S1 134.1(5) . . ?
C4 C5 C6 100.7(5) . . ?
C7 C6 C11 120.4(6) . . ?
C7 C6 C5 129.3(6) . . ?
C11 C6 C5 110.3(5) . . ?
C6 C7 C8 118.7(7) . . ?
C7 C8 C9 120.9(7) . . ?
C10 C9 C8 120.9(7) . . ?
C9 C10 C11 118.5(7) . . ?
C10 C11 C6 120.7(6) . . ?
C10 C11 C3 131.2(6) . . ?
C6 C11 C3 108.1(5) . . ?
C13 C12 C1 111.4(5) . . ?
C13 C12 S3 112.3(5) . . ?
C1 C12 S3 136.2(5) . . ?
C12 C13 C14 112.2(5) . . ?
C12 C13 S2 113.1(5) . . ?
C14 C13 S2 134.6(5) . . ?
C15 C14 C13 111.4(5) . . ?
C15 C14 C22 108.6(5) . . ?
C13 C14 C22 140.1(6) . . ?
C14 C15 C16 112.4(5) . . ?
C14 C15 S3 113.8(5) . . ?
C16 C15 S3 133.8(5) . . ?
C15 C16 C17 100.2(5) . . ?
C18 C17 C22 121.4(6) . . ?
C18 C17 C16 127.9(6) . . ?
C22 C17 C16 110.7(6) . . ?
C17 C18 C19 118.2(6) . . ?
C20 C19 C18 120.9(7) . . ?
C19 C20 C21 120.7(6) . . ?
C22 C21 C20 118.6(6) . . ?
C21 C22 C17 120.1(6) . . ?
C21 C22 C14 131.7(6) . . ?
C17 C22 C14 108.2(5) . . ?
C4 S1 C1 90.3(3) . . ?
C13 S2 C2 90.2(3) . . ?
C15 S3 C12 90.3(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    1.393
_refine_diff_density_min   -0.864
_refine_diff_density_rms    0.146
 
