data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. P. J. Skabara
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H20 O4 S3'
_chemical_formula_sum
 'C21 H20 O4 S3'
_chemical_formula_weight          432.55
 
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)/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                    8.5912(2)
_cell_length_b                    7.70070(10)
_cell_length_c                    30.6182(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.7610(10)
_cell_angle_gamma                 90.00
_cell_volume                      2024.69(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4776
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Slab
_exptl_crystal_colour             Yellow
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.419
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              904
_exptl_absorpt_coefficient_mu     0.391
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9259
_exptl_absorpt_correction_T_max   0.9769
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(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        'φ and ω 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             20897
_diffrn_reflns_av_R_equivalents   0.0626
_diffrn_reflns_av_sigmaI/netI     0.0554
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -39
_diffrn_reflns_limit_l_max        38
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4601
_reflns_number_gt                 3576
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0417P)²+0.8676P] 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        ?
_refine_ls_number_reflns          4601
_refine_ls_number_parameters      333
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0616
_refine_ls_R_factor_gt            0.0423
_refine_ls_wR_factor_ref          0.1070
_refine_ls_wR_factor_gt           0.0973
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_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
C1 C 0.8616(2) 0.0218(3) 0.91508(7) 0.0279(4) Uani 1 1 d . . .
C2 C 0.7833(2) -0.1201(3) 0.89881(7) 0.0280(4) Uani 1 1 d . . .
C3 C 0.8562(2) -0.1996(3) 0.86246(7) 0.0281(4) Uani 1 1 d . . .
C4 C 0.9899(2) -0.1195(3) 0.85048(7) 0.0276(4) Uani 1 1 d . . .
C5 C 0.6636(4) -0.4288(3) 0.89107(10) 0.0473(6) Uani 1 1 d . . .
C6 C 0.8300(2) 0.1337(3) 0.95284(7) 0.0276(4) Uani 1 1 d . . .
C7 C 0.6780(2) 0.1877(3) 0.96193(7) 0.0281(4) Uani 1 1 d . . .
C8 C 0.6489(3) 0.2890(3) 0.99791(7) 0.0311(5) Uani 1 1 d . . .
C9 C 0.7717(3) 0.3389(3) 1.02615(7) 0.0316(5) Uani 1 1 d . . .
C10 C 0.9228(3) 0.2915(3) 1.01771(7) 0.0340(5) Uani 1 1 d . . .
C11 C 0.9499(3) 0.1904(3) 0.98108(7) 0.0323(5) Uani 1 1 d . . .
C12 C 0.4058(3) 0.1526(4) 0.94516(10) 0.0442(6) Uani 1 1 d . . .
C13 C 0.8471(3) 0.4883(4) 1.09187(8) 0.0430(6) Uani 1 1 d . . .
C14 C 1.0987(2) -0.1624(3) 0.81604(7) 0.0276(4) Uani 1 1 d . . .
C15 C 1.0448(2) -0.1974(3) 0.77336(7) 0.0269(4) Uani 1 1 d . . .
C16 C 1.1472(2) -0.2376(3) 0.74061(7) 0.0303(5) Uani 1 1 d . . .
C17 C 1.3063(2) -0.2415(3) 0.75041(7) 0.0348(5) Uani 1 1 d . . .
C18 C 1.3625(3) -0.2065(3) 0.79240(8) 0.0387(5) Uani 1 1 d . . .
C19 C 1.2596(2) -0.1678(3) 0.82461(8) 0.0349(5) Uani 1 1 d . . .
C20 C 0.8239(3) -0.2009(4) 0.72331(8) 0.0392(6) Uani 1 1 d . . .
C21 C 1.3656(3) -0.3467(3) 0.67927(8) 0.0381(5) Uani 1 1 d . . .
O1 O 0.56456(16) 0.13553(19) 0.93254(5) 0.0350(4) Uani 1 1 d . . .
O2 O 0.72696(19) 0.43478(19) 1.06137(5) 0.0396(4) Uani 1 1 d . . .
O3 O 0.88693(15) -0.18422(19) 0.76674(5) 0.0317(3) Uani 1 1 d . . .
O4 O 1.41619(18) -0.2783(2) 0.72036(6) 0.0470(4) Uani 1 1 d . . .
S1 S 1.02379(6) 0.06051(7) 0.883906(17) 0.03014(14) Uani 1 1 d . . .
S2 S 0.61230(7) -0.22228(7) 0.915870(19) 0.03688(16) Uani 1 1 d . . .
S3 S 0.76367(7) -0.38465(7) 0.840515(19) 0.03607(15) Uani 1 1 d . . .
H5A H 0.738(3) -0.489(3) 0.9123(8) 0.040(7) Uiso 1 1 d . . .
H5B H 0.573(3) -0.489(4) 0.8842(8) 0.053(8) Uiso 1 1 d . . .
H8 H 0.547(3) 0.324(3) 1.0040(8) 0.038(6) Uiso 1 1 d . . .
H10 H 1.005(3) 0.321(3) 1.0354(8) 0.039(6) Uiso 1 1 d . . .
H11 H 1.053(3) 0.154(3) 0.9766(8) 0.041(7) Uiso 1 1 d . . .
H12A H 0.383(3) 0.270(3) 0.9470(7) 0.035(6) Uiso 1 1 d . . .
H12B H 0.389(3) 0.094(4) 0.9732(11) 0.066(9) Uiso 1 1 d . . .
H12C H 0.347(3) 0.094(4) 0.9202(9) 0.061(8) Uiso 1 1 d . . .
H13A H 0.797(3) 0.548(3) 1.1150(8) 0.045(7) Uiso 1 1 d . . .
H13B H 0.925(3) 0.564(3) 1.0788(8) 0.040(7) Uiso 1 1 d . . .
H13C H 0.900(3) 0.385(3) 1.1039(8) 0.046(7) Uiso 1 1 d . . .
H16 H 1.110(2) -0.261(3) 0.7137(7) 0.029(6) Uiso 1 1 d . . .
H18 H 1.465(3) -0.214(3) 0.8004(8) 0.047(7) Uiso 1 1 d . . .
H19 H 1.300(3) -0.142(3) 0.8544(8) 0.037(6) Uiso 1 1 d . . .
H20A H 0.839(3) -0.316(4) 0.7116(8) 0.048(7) Uiso 1 1 d . . .
H20B H 0.870(3) -0.110(3) 0.7047(9) 0.046(7) Uiso 1 1 d . . .
H20C H 0.714(3) -0.173(3) 0.7245(8) 0.047(7) Uiso 1 1 d . . .
H21A H 1.462(3) -0.372(3) 0.6631(8) 0.050(7) Uiso 1 1 d . . .
H21B H 1.299(3) -0.262(4) 0.6620(9) 0.060(8) Uiso 1 1 d . . .
H21C H 1.302(3) -0.454(3) 0.6844(8) 0.044(7) Uiso 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 1.369(3) . ?
C1 C6 1.474(3) . ?
C1 S1 1.739(2) . ?
C2 C3 1.431(3) . ?
C2 S2 1.760(2) . ?
C3 C4 1.364(3) . ?
C3 S3 1.755(2) . ?
C4 C14 1.468(3) . ?
C4 S1 1.742(2) . ?
C5 S2 1.823(3) . ?
C5 S3 1.825(3) . ?
C5 H5A 1.01(2) . ?
C5 H5B 0.93(3) . ?
C6 C11 1.394(3) . ?
C6 C7 1.407(3) . ?
C7 O1 1.366(2) . ?
C7 C8 1.379(3) . ?
C8 C9 1.397(3) . ?
C8 H8 0.94(2) . ?
C9 O2 1.372(2) . ?
C9 C10 1.380(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.91(2) . ?
C11 H11 0.95(2) . ?
C12 O1 1.435(3) . ?
C12 H12A 0.93(2) . ?
C12 H12B 0.99(3) . ?
C12 H12C 1.01(3) . ?
C13 O2 1.431(3) . ?
C13 H13A 0.96(3) . ?
C13 H13B 0.98(3) . ?
C13 H13C 0.98(3) . ?
C14 C19 1.399(3) . ?
C14 C15 1.399(3) . ?
C15 O3 1.369(2) . ?
C15 C16 1.389(3) . ?
C16 C17 1.391(3) . ?
C16 H16 0.89(2) . ?
C17 O4 1.368(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.91(3) . ?
C19 H19 0.99(2) . ?
C20 O3 1.426(3) . ?
C20 H20A 0.97(3) . ?
C20 H20B 0.99(3) . ?
C20 H20C 0.97(3) . ?
C21 O4 1.420(3) . ?
C21 H21A 0.99(3) . ?
C21 H21B 1.01(3) . ?
C21 H21C 1.01(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 C6 130.70(19) . . ?
C2 C1 S1 109.28(15) . . ?
C6 C1 S1 120.02(15) . . ?
C1 C2 C3 113.74(18) . . ?
C1 C2 S2 130.86(16) . . ?
C3 C2 S2 115.38(15) . . ?
C4 C3 C2 114.07(18) . . ?
C4 C3 S3 129.75(16) . . ?
C2 C3 S3 116.17(15) . . ?
C3 C4 C14 130.65(19) . . ?
C3 C4 S1 109.19(15) . . ?
C14 C4 S1 120.16(15) . . ?
S2 C5 S3 108.48(13) . . ?
S2 C5 H5A 106.9(14) . . ?
S3 C5 H5A 109.0(14) . . ?
S2 C5 H5B 108.6(17) . . ?
S3 C5 H5B 108.4(16) . . ?
H5A C5 H5B 115(2) . . ?
C11 C6 C7 117.20(19) . . ?
C11 C6 C1 121.31(19) . . ?
C7 C6 C1 121.49(18) . . ?
O1 C7 C8 123.34(19) . . ?
O1 C7 C6 115.49(18) . . ?
C8 C7 C6 121.16(19) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.9(15) . . ?
C9 C8 H8 119.2(14) . . ?
O2 C9 C10 125.3(2) . . ?
O2 C9 C8 114.22(19) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C11 118.7(2) . . ?
C9 C10 H10 123.0(15) . . ?
C11 C10 H10 118.2(16) . . ?
C10 C11 C6 122.5(2) . . ?
C10 C11 H11 117.6(15) . . ?
C6 C11 H11 119.8(15) . . ?
O1 C12 H12A 108.2(15) . . ?
O1 C12 H12B 111.2(17) . . ?
H12A C12 H12B 111(2) . . ?
O1 C12 H12C 102.4(16) . . ?
H12A C12 H12C 112(2) . . ?
H12B C12 H12C 112(2) . . ?
O2 C13 H13A 106.9(15) . . ?
O2 C13 H13B 113.0(14) . . ?
H13A C13 H13B 110(2) . . ?
O2 C13 H13C 109.2(15) . . ?
H13A C13 H13C 109(2) . . ?
H13B C13 H13C 108(2) . . ?
C19 C14 C15 117.78(19) . . ?
C19 C14 C4 121.28(19) . . ?
C15 C14 C4 120.94(17) . . ?
O3 C15 C16 123.79(19) . . ?
O3 C15 C14 114.96(17) . . ?
C16 C15 C14 121.22(18) . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16 119.5(14) . . ?
C17 C16 H16 121.2(14) . . ?
O4 C17 C18 115.88(19) . . ?
O4 C17 C16 123.6(2) . . ?
C18 C17 C16 120.5(2) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 117.3(16) . . ?
C17 C18 H18 123.0(16) . . ?
C18 C19 C14 121.6(2) . . ?
C18 C19 H19 119.6(13) . . ?
C14 C19 H19 118.8(13) . . ?
O3 C20 H20A 112.1(15) . . ?
O3 C20 H20B 109.1(15) . . ?
H20A C20 H20B 112(2) . . ?
O3 C20 H20C 106.7(15) . . ?
H20A C20 H20C 111(2) . . ?
H20B C20 H20C 106(2) . . ?
O4 C21 H21A 106.1(15) . . ?
O4 C21 H21B 112.4(16) . . ?
H21A C21 H21B 110(2) . . ?
O4 C21 H21C 108.6(14) . . ?
H21A C21 H21C 112(2) . . ?
H21B C21 H21C 108(2) . . ?
C7 O1 C12 117.40(18) . . ?
C9 O2 C13 117.03(19) . . ?
C15 O3 C20 118.52(17) . . ?
C17 O4 C21 118.30(17) . . ?
C1 S1 C4 93.66(10) . . ?
C2 S2 C5 92.97(11) . . ?
C3 S3 C5 92.66(11) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.336
_refine_diff_density_min   -0.318
_refine_diff_density_rms    0.058
