data_00src426
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H16 O3 S3'
_chemical_formula_weight          388.50
 
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'
 '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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.349(2)
_cell_length_b                    12.081(2)
_cell_length_c                    15.099(3)
_cell_angle_alpha                 91.00(3)
_cell_angle_beta                  103.07(3)
_cell_angle_gamma                 90.72(3)
_cell_volume                      1838.3(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     19216
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.404
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              808
_exptl_absorpt_coefficient_mu     0.418
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9210
_exptl_absorpt_correction_T_max   0.9594
_exptl_absorpt_process_details    'SORTAV (Blessing, 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 KappaCCD Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             27358
_diffrn_reflns_av_R_equivalents   0.0490
_diffrn_reflns_av_sigmaI/netI     0.0542
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.04
_diffrn_reflns_theta_max          27.49
_reflns_number_total              8248
_reflns_number_gt                 6108
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.0460P)²+0.5015P] 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        0.0032(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          8248
_refine_ls_number_parameters      456
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0651
_refine_ls_R_factor_gt            0.0412
_refine_ls_wR_factor_ref          0.1038
_refine_ls_wR_factor_gt           0.0948
_refine_ls_goodness_of_fit_ref    1.021
_refine_ls_restrained_S_all       1.021
_refine_ls_shift/su_max           0.002
_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 0.8309(2) 0.35761(17) 0.40131(13) 0.0332(5) Uani 1 1 d . . .
C2 C 0.88063(19) 0.53889(16) 0.32902(13) 0.0294(4) Uani 1 1 d . . .
C3 C 0.99856(19) 0.49802(16) 0.36563(13) 0.0287(4) Uani 1 1 d . . .
C4 C 0.89482(19) 0.64585(16) 0.28217(14) 0.0298(4) Uani 1 1 d . . .
H4 H 0.8523 0.6370 0.2160 0.036 Uiso 1 1 calc R . .
C5 C 1.10862(19) 0.57114(16) 0.34600(14) 0.0297(4) Uani 1 1 d . . .
H5 H 1.1650 0.6024 0.4039 0.036 Uiso 1 1 calc R . .
C6 C 0.83912(18) 0.74587(15) 0.32030(13) 0.0268(4) Uani 1 1 d . . .
C7 C 0.9181(2) 0.83117(17) 0.36601(14) 0.0337(5) Uani 1 1 d . . .
H7 H 1.0119 0.8260 0.3768 0.040 Uiso 1 1 calc R . .
C8 C 0.8628(2) 0.92429(18) 0.39648(15) 0.0396(5) Uani 1 1 d . . .
H8 H 0.9183 0.9828 0.4272 0.048 Uiso 1 1 calc R . .
C9 C 0.7272(2) 0.93157(18) 0.38197(14) 0.0366(5) Uani 1 1 d . . .
H9 H 0.6893 0.9956 0.4024 0.044 Uiso 1 1 calc R . .
C10 C 0.6453(2) 0.84625(17) 0.33782(14) 0.0326(5) Uani 1 1 d . . .
H10 H 0.5517 0.8507 0.3292 0.039 Uiso 1 1 calc R . .
C11 C 0.70175(18) 0.75472(15) 0.30653(13) 0.0272(4) Uani 1 1 d . . .
C12 C 0.4914(2) 0.6636(2) 0.25102(18) 0.0496(6) Uani 1 1 d . . .
H12A H 0.4705 0.6673 0.3111 0.074 Uiso 1 1 calc R . .
H12B H 0.4543 0.5948 0.2195 0.074 Uiso 1 1 calc R . .
H12C H 0.4528 0.7271 0.2155 0.074 Uiso 1 1 calc R . .
C13 C 1.19279(18) 0.51107(16) 0.29196(13) 0.0273(4) Uani 1 1 d . . .
C14 C 1.17715(19) 0.52215(17) 0.19970(13) 0.0312(4) Uani 1 1 d . . .
H14 H 1.1161 0.5742 0.1685 0.037 Uiso 1 1 calc R . .
C15 C 1.2493(2) 0.45830(19) 0.15175(15) 0.0404(5) Uani 1 1 d . . .
H15 H 1.2369 0.4658 0.0879 0.049 Uiso 1 1 calc R . .
C16 C 1.3386(2) 0.38414(19) 0.19701(17) 0.0457(6) Uani 1 1 d . . .
H16 H 1.3869 0.3395 0.1638 0.055 Uiso 1 1 calc R . .
C17 C 1.3597(2) 0.37319(18) 0.28992(17) 0.0431(6) Uani 1 1 d . . .
H17 H 1.4235 0.3230 0.3208 0.052 Uiso 1 1 calc R . .
C18 C 1.2865(2) 0.43636(17) 0.33748(14) 0.0345(5) Uani 1 1 d . . .
C19 C 1.3831(4) 0.3520(3) 0.4784(2) 0.0866(11) Uani 1 1 d . . .
H19A H 1.3564 0.2774 0.4540 0.130 Uiso 1 1 calc R . .
H19B H 1.3801 0.3560 0.5428 0.130 Uiso 1 1 calc R . .
H19C H 1.4736 0.3684 0.4723 0.130 Uiso 1 1 calc R . .
C20 C 0.6997(2) 0.84941(17) 0.08089(13) 0.0310(4) Uani 1 1 d . . .
C21 C 0.54653(19) 0.99325(15) 0.12857(12) 0.0260(4) Uani 1 1 d . . .
C22 C 0.66783(19) 1.03745(15) 0.15339(12) 0.0264(4) Uani 1 1 d . . .
C23 C 0.44660(19) 1.06932(15) 0.15610(13) 0.0275(4) Uani 1 1 d . . .
H23 H 0.3756 1.0871 0.1016 0.033 Uiso 1 1 calc R . .
C24 C 0.66452(19) 1.14924(16) 0.19845(13) 0.0280(4) Uani 1 1 d . . .
H24 H 0.7077 1.1446 0.2646 0.034 Uiso 1 1 calc R . .
C25 C 0.38491(18) 1.02218(15) 0.22915(13) 0.0259(4) Uani 1 1 d . . .
C26 C 0.41732(19) 1.06133(17) 0.31800(13) 0.0303(4) Uani 1 1 d . . .
H26 H 0.4780 1.1219 0.3341 0.036 Uiso 1 1 calc R . .
C27 C 0.3626(2) 1.0135(2) 0.38375(15) 0.0394(5) Uani 1 1 d . . .
H27 H 0.3851 1.0411 0.4447 0.047 Uiso 1 1 calc R . .
C28 C 0.2750(2) 0.9251(2) 0.36012(16) 0.0459(6) Uani 1 1 d . . .
H28 H 0.2391 0.8910 0.4057 0.055 Uiso 1 1 calc R . .
C29 C 0.2385(2) 0.88508(18) 0.27125(16) 0.0389(5) Uani 1 1 d . . .
H29 H 0.1768 0.8251 0.2554 0.047 Uiso 1 1 calc R . .
C30 C 0.29373(19) 0.93444(16) 0.20610(14) 0.0301(4) Uani 1 1 d . . .
C31 C 0.1714(3) 0.8173(2) 0.08481(19) 0.0602(7) Uani 1 1 d . . .
H31A H 0.2002 0.7498 0.1181 0.090 Uiso 1 1 calc R . .
H31B H 0.1632 0.8034 0.0196 0.090 Uiso 1 1 calc R . .
H31C H 0.0853 0.8393 0.0955 0.090 Uiso 1 1 calc R . .
C32 C 0.72661(19) 1.24314(16) 0.15792(13) 0.0279(4) Uani 1 1 d . . .
C33 C 0.6525(2) 1.32471(17) 0.10715(13) 0.0317(4) Uani 1 1 d . . .
H33 H 0.5584 1.3205 0.0943 0.038 Uiso 1 1 calc R . .
C34 C 0.7156(2) 1.41264(18) 0.07498(15) 0.0414(5) Uani 1 1 d . . .
H34 H 0.6649 1.4691 0.0411 0.050 Uiso 1 1 calc R . .
C35 C 0.8516(2) 1.41726(19) 0.09252(17) 0.0461(6) Uani 1 1 d . . .
H35 H 0.8945 1.4779 0.0712 0.055 Uiso 1 1 calc R . .
C36 C 0.9275(2) 1.33542(19) 0.14064(16) 0.0431(6) Uani 1 1 d . . .
H36 H 1.0215 1.3383 0.1508 0.052 Uiso 1 1 calc R . .
C37 C 0.8639(2) 1.24893(17) 0.17382(14) 0.0338(5) Uani 1 1 d . . .
C38 C 1.0694(2) 1.1604(2) 0.2373(2) 0.0642(8) Uani 1 1 d . . .
H38A H 1.0938 1.1539 0.1785 0.096 Uiso 1 1 calc R . .
H38B H 1.1025 1.0965 0.2743 0.096 Uiso 1 1 calc R . .
H38C H 1.1085 1.2286 0.2689 0.096 Uiso 1 1 calc R . .
O1 O 1.03638(13) 0.65740(11) 0.29338(10) 0.0381(4) Uani 1 1 d . . .
O2 O 0.63181(13) 0.66599(11) 0.26119(11) 0.0390(4) Uani 1 1 d . . .
O3 O 1.29416(16) 0.43115(14) 0.42897(10) 0.0485(4) Uani 1 1 d . . .
O4 O 0.52486(13) 1.16657(11) 0.18826(10) 0.0334(3) Uani 1 1 d . . .
O5 O 0.26685(14) 0.90395(12) 0.11560(10) 0.0407(4) Uani 1 1 d . . .
O6 O 0.92823(14) 1.16367(13) 0.22326(11) 0.0449(4) Uani 1 1 d . . .
S1 S 0.75545(6) 0.25211(5) 0.43791(4) 0.04380(16) Uani 1 1 d . . .
S2 S 0.74277(5) 0.46404(4) 0.34087(4) 0.03249(13) Uani 1 1 d . . .
S3 S 1.00183(5) 0.37415(4) 0.42094(3) 0.03389(14) Uani 1 1 d . . .
S4 S 0.76109(6) 0.74054(5) 0.03854(4) 0.04542(16) Uani 1 1 d . . .
S5 S 0.79727(5) 0.96096(4) 0.13219(4) 0.03169(13) Uani 1 1 d . . .
S6 S 0.53174(5) 0.86398(4) 0.07689(3) 0.03085(13) 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 S1 1.654(2) . ?
C1 S3 1.735(2) . ?
C1 S2 1.735(2) . ?
C2 C3 1.326(3) . ?
C2 C4 1.505(3) . ?
C2 S2 1.724(2) . ?
C3 C5 1.517(3) . ?
C3 S3 1.723(2) . ?
C4 O1 1.441(2) . ?
C4 C6 1.506(3) . ?
C5 O1 1.434(2) . ?
C5 C13 1.506(3) . ?
C6 C7 1.380(3) . ?
C6 C11 1.395(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.382(3) . ?
C11 O2 1.368(2) . ?
C12 O2 1.427(3) . ?
C13 C14 1.375(3) . ?
C13 C18 1.404(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.372(3) . ?
C16 C17 1.379(3) . ?
C17 C18 1.383(3) . ?
C18 O3 1.368(3) . ?
C19 O3 1.434(3) . ?
C20 S4 1.649(2) . ?
C20 S5 1.735(2) . ?
C20 S6 1.737(2) . ?
C21 C22 1.328(3) . ?
C21 C23 1.514(3) . ?
C21 S6 1.723(2) . ?
C22 C24 1.506(3) . ?
C22 S5 1.722(2) . ?
C23 O4 1.432(2) . ?
C23 C25 1.510(3) . ?
C24 O4 1.437(2) . ?
C24 C32 1.503(3) . ?
C25 C26 1.381(3) . ?
C25 C30 1.396(3) . ?
C26 C27 1.381(3) . ?
C27 C28 1.380(3) . ?
C28 C29 1.386(3) . ?
C29 C30 1.385(3) . ?
C30 O5 1.374(2) . ?
C31 O5 1.427(3) . ?
C32 C37 1.387(3) . ?
C32 C33 1.388(3) . ?
C33 C34 1.391(3) . ?
C34 C35 1.372(3) . ?
C35 C36 1.381(3) . ?
C36 C37 1.388(3) . ?
C37 O6 1.371(3) . ?
C38 O6 1.429(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
S1 C1 S3 124.05(13) . . ?
S1 C1 S2 121.82(13) . . ?
S3 C1 S2 114.12(12) . . ?
C3 C2 C4 110.85(17) . . ?
C3 C2 S2 117.38(16) . . ?
C4 C2 S2 131.77(15) . . ?
C2 C3 C5 110.72(17) . . ?
C2 C3 S3 117.40(16) . . ?
C5 C3 S3 131.82(15) . . ?
O1 C4 C6 110.88(16) . . ?
O1 C4 C2 102.74(15) . . ?
C6 C4 C2 115.25(16) . . ?
O1 C5 C13 110.44(16) . . ?
O1 C5 C3 102.48(15) . . ?
C13 C5 C3 112.41(16) . . ?
C7 C6 C11 118.40(18) . . ?
C7 C6 C4 122.76(18) . . ?
C11 C6 C4 118.81(17) . . ?
C6 C7 C8 121.03(19) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C10 120.6(2) . . ?
C11 C10 C9 119.06(19) . . ?
O2 C11 C10 124.64(18) . . ?
O2 C11 C6 114.18(17) . . ?
C10 C11 C6 121.18(18) . . ?
C14 C13 C18 118.86(18) . . ?
C14 C13 C5 122.90(18) . . ?
C18 C13 C5 118.16(17) . . ?
C13 C14 C15 120.8(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C17 121.2(2) . . ?
C16 C17 C18 119.1(2) . . ?
O3 C18 C17 125.1(2) . . ?
O3 C18 C13 114.34(17) . . ?
C17 C18 C13 120.5(2) . . ?
S4 C20 S5 122.87(13) . . ?
S4 C20 S6 123.25(13) . . ?
S5 C20 S6 113.88(11) . . ?
C22 C21 C23 110.36(17) . . ?
C22 C21 S6 117.04(15) . . ?
C23 C21 S6 132.56(15) . . ?
C21 C22 C24 110.68(17) . . ?
C21 C22 S5 117.61(15) . . ?
C24 C22 S5 131.69(14) . . ?
O4 C23 C25 111.30(16) . . ?
O4 C23 C21 102.54(15) . . ?
C25 C23 C21 113.18(16) . . ?
O4 C24 C32 110.34(16) . . ?
O4 C24 C22 102.67(15) . . ?
C32 C24 C22 115.68(16) . . ?
C26 C25 C30 118.99(18) . . ?
C26 C25 C23 122.39(18) . . ?
C30 C25 C23 118.61(17) . . ?
C25 C26 C27 120.8(2) . . ?
C28 C27 C26 119.4(2) . . ?
C27 C28 C29 121.3(2) . . ?
C30 C29 C28 118.5(2) . . ?
O5 C30 C29 125.07(19) . . ?
O5 C30 C25 113.97(17) . . ?
C29 C30 C25 120.97(19) . . ?
C37 C32 C33 119.10(18) . . ?
C37 C32 C24 118.12(18) . . ?
C33 C32 C24 122.77(18) . . ?
C32 C33 C34 120.3(2) . . ?
C35 C34 C33 119.6(2) . . ?
C34 C35 C36 121.3(2) . . ?
C35 C36 C37 118.8(2) . . ?
O6 C37 C32 114.81(18) . . ?
O6 C37 C36 124.24(19) . . ?
C32 C37 C36 120.9(2) . . ?
C5 O1 C4 113.13(15) . . ?
C11 O2 C12 117.95(17) . . ?
C18 O3 C19 116.93(19) . . ?
C23 O4 C24 112.64(14) . . ?
C30 O5 C31 118.14(18) . . ?
C37 O6 C38 117.89(19) . . ?
C2 S2 C1 95.53(10) . . ?
C3 S3 C1 95.57(10) . . ?
C22 S5 C20 95.62(10) . . ?
C21 S6 C20 95.83(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.977
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.977
_refine_diff_density_max    0.324
_refine_diff_density_min   -0.350
_refine_diff_density_rms    0.054
