data_05src0198
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. C. D. Gabbutt
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H18 O2 S2'
_chemical_formula_sum
 'C21 H18 O2 S2'
_chemical_formula_weight          366.47
 
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'
 '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            monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    11.554(2)
_cell_length_b                    9.2919(17)
_cell_length_c                    17.255(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.194(12)
_cell_angle_gamma                 90.00
_cell_volume                      1810.6(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4279
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Rod
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.344
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              768
_exptl_absorpt_coefficient_mu     0.305
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9303
_exptl_absorpt_correction_T_max   0.9909
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_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    '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & 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             19643
_diffrn_reflns_av_R_equivalents   0.0597
_diffrn_reflns_av_sigmaI/netI     0.0571
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4136
_reflns_number_gt                 3232
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_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)+(0.0000P)²+2.3068P] 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        0.0086(15)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4136
_refine_ls_number_parameters      363
_refine_ls_number_restraints      534
_refine_ls_R_factor_all           0.0908
_refine_ls_R_factor_gt            0.0664
_refine_ls_wR_factor_ref          0.1232
_refine_ls_wR_factor_gt           0.1163
_refine_ls_goodness_of_fit_ref    1.210
_refine_ls_restrained_S_all       1.139
_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 -0.0225(2) 0.3660(3) -0.17241(16) 0.0330(6) Uani 1 1 d U A .
C2 C 0.1008(2) 0.4014(3) -0.13709(16) 0.0317(6) Uani 1 1 d U . .
C3 C 0.1385(2) 0.5393(3) -0.13289(15) 0.0294(6) Uani 1 1 d U A .
C4 C 0.0560(2) 0.6540(3) -0.16381(15) 0.0284(6) Uani 1 1 d U . .
C5 C -0.0607(2) 0.6180(3) -0.19753(15) 0.0302(6) Uani 1 1 d U A .
C6 C -0.1445(2) 0.7212(3) -0.22888(16) 0.0350(7) Uani 1 1 d U . .
H6 H -0.2233 0.6942 -0.2525 0.042 Uiso 1 1 calc R A .
C7 C -0.1106(3) 0.8631(3) -0.22491(17) 0.0366(7) Uani 1 1 d U A .
H7 H -0.1671 0.9350 -0.2459 0.044 Uiso 1 1 calc R . .
C8 C 0.0046(3) 0.9037(3) -0.19086(16) 0.0354(7) Uani 1 1 d U . .
H8 H 0.0264 1.0025 -0.1881 0.043 Uiso 1 1 calc R A .
C9 C 0.0871(2) 0.7999(3) -0.16110(16) 0.0319(6) Uani 1 1 d U A .
H9 H 0.1662 0.8275 -0.1385 0.038 Uiso 1 1 calc R . .
O1 O -0.09779(16) 0.47715(19) -0.20188(11) 0.0342(5) Uani 1 1 d U . .
O2 O -0.06505(17) 0.2470(2) -0.17871(12) 0.0402(5) Uani 1 1 d U . .
C11 C 0.1708(4) 0.1960(4) -0.0475(2) 0.0317(9) Uani 0.855(3) 1 d PDU A 1
C12 C 0.1809(4) 0.2778(5) -0.1112(2) 0.0270(9) Uani 0.855(3) 1 d PDU A 1
C13 C 0.2733(3) 0.2307(4) -0.1482(2) 0.0279(8) Uani 0.855(3) 1 d PDU A 1
H13 H 0.2925 0.2780 -0.1927 0.033 Uiso 0.855(3) 1 calc PR A 1
C14 C 0.3316(3) 0.1121(3) -0.11410(19) 0.0297(7) Uani 0.855(3) 1 d PDU A 1
C15 C 0.0849(4) 0.2088(5) 0.0056(2) 0.0500(11) Uani 0.855(3) 1 d PDU A 1
H15A H 0.0628 0.3100 0.0093 0.075 Uiso 0.855(3) 1 calc PR A 1
H15B H 0.1215 0.1729 0.0585 0.075 Uiso 0.855(3) 1 calc PR A 1
H15C H 0.0141 0.1520 -0.0162 0.075 Uiso 0.855(3) 1 calc PR A 1
C16 C 0.4319(3) 0.0325(4) -0.1365(2) 0.0386(9) Uani 0.855(3) 1 d PDU A 1
H16A H 0.4017 -0.0544 -0.1661 0.058 Uiso 0.855(3) 1 calc PR A 1
H16B H 0.4895 0.0055 -0.0885 0.058 Uiso 0.855(3) 1 calc PR A 1
H16C H 0.4703 0.0943 -0.1697 0.058 Uiso 0.855(3) 1 calc PR A 1
S11 S 0.27496(12) 0.05957(12) -0.03376(7) 0.0313(3) Uani 0.855(3) 1 d PDU A 1
C111 C 0.2576(16) 0.2152(18) -0.1125(10) 0.021(3) Uani 0.145(3) 1 d PDU A 2
C112 C 0.165(2) 0.271(3) -0.0852(14) 0.020(4) Uani 0.145(3) 1 d PDU A 2
C113 C 0.1351(17) 0.189(2) -0.0237(13) 0.023(4) Uani 0.145(3) 1 d PDU A 2
H113 H 0.0673 0.2092 -0.0026 0.028 Uiso 0.145(3) 1 calc PR A 2
C114 C 0.2102(15) 0.0782(17) 0.0034(9) 0.030(4) Uani 0.145(3) 1 d PDU A 2
C115 C 0.3091(19) 0.260(3) -0.1814(11) 0.041(5) Uani 0.145(3) 1 d PDU A 2
H11A H 0.2490 0.3110 -0.2201 0.061 Uiso 0.145(3) 1 calc PR A 2
H11B H 0.3348 0.1740 -0.2063 0.061 Uiso 0.145(3) 1 calc PR A 2
H11C H 0.3771 0.3230 -0.1629 0.061 Uiso 0.145(3) 1 calc PR A 2
C116 C 0.2087(18) -0.023(2) 0.0713(10) 0.040(5) Uani 0.145(3) 1 d PDU A 2
H11D H 0.2643 0.0114 0.1186 0.060 Uiso 0.145(3) 1 calc PR A 2
H11E H 0.2320 -0.1193 0.0575 0.060 Uiso 0.145(3) 1 calc PR A 2
H11F H 0.1287 -0.0263 0.0819 0.060 Uiso 0.145(3) 1 calc PR A 2
S111 S 0.3129(6) 0.0648(8) -0.0573(5) 0.0353(18) Uani 0.145(3) 1 d PDU A 2
C21 C 0.2995(4) 0.6327(7) -0.0231(3) 0.0300(13) Uani 0.805(14) 1 d PDU A 1
C22 C 0.2662(7) 0.5838(17) -0.0990(3) 0.0253(12) Uani 0.805(14) 1 d PDU A 1
C23 C 0.3583(5) 0.5923(10) -0.1418(3) 0.0298(14) Uani 0.805(14) 1 d PDU A 1
H23 H 0.3490 0.5634 -0.1956 0.036 Uiso 0.805(14) 1 calc PR A 1
C24 C 0.4607(5) 0.6455(8) -0.0984(3) 0.0297(11) Uani 0.805(14) 1 d PDU A 1
C25 C 0.2271(4) 0.6501(8) 0.0383(3) 0.0428(14) Uani 0.805(14) 1 d PDU A 1
H25A H 0.1922 0.7467 0.0343 0.064 Uiso 0.805(14) 1 calc PR A 1
H25B H 0.2777 0.6372 0.0911 0.064 Uiso 0.805(14) 1 calc PR A 1
H25C H 0.1638 0.5779 0.0299 0.064 Uiso 0.805(14) 1 calc PR A 1
C26 C 0.5767(6) 0.6688(7) -0.1236(4) 0.0410(13) Uani 0.805(14) 1 d PDU A 1
H26A H 0.5724 0.6261 -0.1761 0.062 Uiso 0.805(14) 1 calc PR A 1
H26B H 0.6408 0.6233 -0.0852 0.062 Uiso 0.805(14) 1 calc PR A 1
H26C H 0.5921 0.7723 -0.1260 0.062 Uiso 0.805(14) 1 calc PR A 1
S21 S 0.4453(2) 0.6868(4) -0.00410(15) 0.0313(5) Uani 0.805(14) 1 d PDU A 1
C121 C 0.2832(18) 0.594(3) -0.0077(12) 0.032(4) Uani 0.195(14) 1 d PDU A 2
C122 C 0.247(3) 0.577(7) -0.0874(14) 0.024(4) Uani 0.195(14) 1 d PDU A 2
C123 C 0.335(2) 0.610(5) -0.1299(15) 0.038(6) Uani 0.195(14) 1 d PDU A 2
H123 H 0.3249 0.5958 -0.1854 0.046 Uiso 0.195(14) 1 calc PR A 2
C124 C 0.436(2) 0.664(4) -0.0836(16) 0.051(6) Uani 0.195(14) 1 d PDU A 2
C125 C 0.2168(15) 0.570(3) 0.0563(10) 0.034(5) Uani 0.195(14) 1 d PDU A 2
H12A H 0.1410 0.6206 0.0434 0.051 Uiso 0.195(14) 1 calc PR A 2
H12B H 0.2634 0.6056 0.1067 0.051 Uiso 0.195(14) 1 calc PR A 2
H12C H 0.2024 0.4663 0.0609 0.051 Uiso 0.195(14) 1 calc PR A 2
C126 C 0.548(3) 0.704(4) -0.108(2) 0.085(11) Uani 0.195(14) 1 d PDU A 2
H12D H 0.5951 0.6171 -0.1115 0.128 Uiso 0.195(14) 1 calc PR A 2
H12E H 0.5936 0.7704 -0.0694 0.128 Uiso 0.195(14) 1 calc PR A 2
H12F H 0.5292 0.7507 -0.1605 0.128 Uiso 0.195(14) 1 calc PR A 2
S121 S 0.4250(15) 0.6621(17) 0.0136(12) 0.055(3) Uani 0.195(14) 1 d PDU A 2
 
 
_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 O2 1.206(3) . ?
C1 O1 1.377(3) . ?
C1 C2 1.463(4) . ?
C2 C3 1.350(4) . ?
C2 C12 1.483(4) . ?
C2 C112 1.597(19) . ?
C3 C122 1.38(2) . ?
C3 C4 1.455(3) . ?
C3 C22 1.524(6) . ?
C4 C5 1.391(4) . ?
C4 C9 1.400(4) . ?
C5 O1 1.375(3) . ?
C5 C6 1.388(4) . ?
C6 C7 1.373(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.362(5) . ?
C11 C15 1.490(5) . ?
C11 S11 1.730(4) . ?
C12 C13 1.423(5) . ?
C13 C14 1.359(4) . ?
C13 H13 0.9500 . ?
C14 C16 1.493(4) . ?
C14 S11 1.723(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C111 C112 1.357(15) . ?
C111 C115 1.495(15) . ?
C111 S111 1.735(15) . ?
C112 C113 1.408(16) . ?
C113 C114 1.363(15) . ?
C113 H113 0.9500 . ?
C114 C116 1.503(15) . ?
C114 S111 1.746(13) . ?
C115 H11A 0.9800 . ?
C115 H11B 0.9800 . ?
C115 H11C 0.9800 . ?
C116 H11D 0.9800 . ?
C116 H11E 0.9800 . ?
C116 H11F 0.9800 . ?
C21 C22 1.361(6) . ?
C21 C25 1.492(5) . ?
C21 S21 1.722(4) . ?
C22 C23 1.421(6) . ?
C23 C24 1.353(5) . ?
C23 H23 0.9500 . ?
C24 C26 1.509(5) . ?
C24 S21 1.718(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C121 C122 1.359(15) . ?
C121 C125 1.489(14) . ?
C121 S121 1.721(14) . ?
C122 C123 1.406(16) . ?
C123 C124 1.360(15) . ?
C123 H123 0.9500 . ?
C124 C126 1.499(15) . ?
C124 S121 1.707(15) . ?
C125 H12A 0.9800 . ?
C125 H12B 0.9800 . ?
C125 H12C 0.9800 . ?
C126 H12D 0.9800 . ?
C126 H12E 0.9800 . ?
C126 H12F 0.9800 . ?
 
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
O2 C1 O1 116.1(2) . . ?
O2 C1 C2 125.9(2) . . ?
O1 C1 C2 117.9(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 C12 123.0(3) . . ?
C1 C2 C12 116.2(3) . . ?
C3 C2 C112 125.8(12) . . ?
C1 C2 C112 111.0(11) . . ?
C2 C3 C122 121(3) . . ?
C2 C3 C4 119.8(2) . . ?
C122 C3 C4 118(3) . . ?
C2 C3 C22 123.6(7) . . ?
C4 C3 C22 116.6(6) . . ?
C5 C4 C9 117.8(2) . . ?
C5 C4 C3 118.6(2) . . ?
C9 C4 C3 123.6(2) . . ?
O1 C5 C6 116.9(2) . . ?
O1 C5 C4 121.0(2) . . ?
C6 C5 C4 122.1(3) . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C5 O1 C1 121.9(2) . . ?
C12 C11 C15 129.3(3) . . ?
C12 C11 S11 110.1(3) . . ?
C15 C11 S11 120.6(3) . . ?
C11 C12 C13 113.0(3) . . ?
C11 C12 C2 121.4(3) . . ?
C13 C12 C2 125.6(3) . . ?
C14 C13 C12 113.9(3) . . ?
C14 C13 H13 123.1 . . ?
C12 C13 H13 123.1 . . ?
C13 C14 C16 129.1(3) . . ?
C13 C14 S11 109.9(3) . . ?
C16 C14 S11 121.0(2) . . ?
C14 S11 C11 93.06(18) . . ?
C112 C111 C115 130.2(15) . . ?
C112 C111 S111 110.0(12) . . ?
C115 C111 S111 119.7(13) . . ?
C111 C112 C113 113.2(15) . . ?
C111 C112 C2 113.7(13) . . ?
C113 C112 C2 132.4(13) . . ?
C114 C113 C112 115.2(15) . . ?
C114 C113 H113 122.4 . . ?
C112 C113 H113 122.4 . . ?
C113 C114 C116 128.8(14) . . ?
C113 C114 S111 108.2(11) . . ?
C116 C114 S111 123.0(12) . . ?
C111 C115 H11A 109.5 . . ?
C111 C115 H11B 109.5 . . ?
H11A C115 H11B 109.5 . . ?
C111 C115 H11C 109.5 . . ?
H11A C115 H11C 109.5 . . ?
H11B C115 H11C 109.5 . . ?
C114 C116 H11D 109.5 . . ?
C114 C116 H11E 109.5 . . ?
H11D C116 H11E 109.5 . . ?
C114 C116 H11F 109.5 . . ?
H11D C116 H11F 109.5 . . ?
H11E C116 H11F 109.5 . . ?
C111 S111 C114 93.1(7) . . ?
C22 C21 C25 129.2(4) . . ?
C22 C21 S21 110.3(3) . . ?
C25 C21 S21 120.4(3) . . ?
C21 C22 C23 113.0(4) . . ?
C21 C22 C3 120.9(5) . . ?
C23 C22 C3 125.8(4) . . ?
C24 C23 C22 113.3(4) . . ?
C24 C23 H23 123.3 . . ?
C22 C23 H23 123.3 . . ?
C23 C24 C26 128.2(4) . . ?
C23 C24 S21 110.6(3) . . ?
C26 C24 S21 121.1(3) . . ?
C24 S21 C21 92.7(2) . . ?
C122 C121 C125 129.4(15) . . ?
C122 C121 S121 109.5(12) . . ?
C125 C121 S121 120.9(13) . . ?
C121 C122 C3 131.0(17) . . ?
C121 C122 C123 113.6(15) . . ?
C3 C122 C123 115.3(16) . . ?
C124 C123 C122 113.4(15) . . ?
C124 C123 H123 123.3 . . ?
C122 C123 H123 123.3 . . ?
C123 C124 C126 127.7(18) . . ?
C123 C124 S121 110.1(12) . . ?
C126 C124 S121 121.9(16) . . ?
C121 C125 H12A 109.5 . . ?
C121 C125 H12B 109.5 . . ?
H12A C125 H12B 109.5 . . ?
C121 C125 H12C 109.5 . . ?
H12A C125 H12C 109.5 . . ?
H12B C125 H12C 109.5 . . ?
C124 C126 H12D 109.5 . . ?
C124 C126 H12E 109.5 . . ?
H12D C126 H12E 109.5 . . ?
C124 C126 H12F 109.5 . . ?
H12D C126 H12F 109.5 . . ?
H12E C126 H12F 109.5 . . ?
C124 S121 C121 93.2(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.216
_refine_diff_density_min   -0.229
_refine_diff_density_rms    0.053
