data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Pete Skabara
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H22 O4 S3'
_chemical_formula_sum
 'C22 H22 O4 S3'
_chemical_formula_weight          446.58
 
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
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.6143(2)
_cell_length_b                    8.8758(2)
_cell_length_c                    13.8928(4)
_cell_angle_alpha                 77.3640(10)
_cell_angle_beta                  85.6280(10)
_cell_angle_gamma                 79.319(2)
_cell_volume                      1017.84(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     15460
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.457
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              468
_exptl_absorpt_coefficient_mu     0.392
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8591
_exptl_absorpt_correction_T_max   0.9619
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             12996
_diffrn_reflns_av_R_equivalents   0.0527
_diffrn_reflns_av_sigmaI/netI     0.0424
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4472
_reflns_number_gt                 4085
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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)+(0.0631P)²+0.6509P] 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
_refine_ls_number_reflns          4472
_refine_ls_number_parameters      267
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0458
_refine_ls_R_factor_gt            0.0411
_refine_ls_wR_factor_ref          0.1142
_refine_ls_wR_factor_gt           0.1106
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.033
_refine_ls_shift/su_max           0.030
_refine_ls_shift/su_mean          0.002
 
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 0.12139(19) 0.62112(19) 0.09416(12) 0.0149(3) Uani 1 1 d . . .
C2 C 0.16872(19) 0.76530(19) 0.09179(12) 0.0148(3) Uani 1 1 d . . .
C3 C 0.2718(2) 0.8247(2) 0.01818(12) 0.0170(3) Uani 1 1 d . . .
H3 H 0.3003 0.9237 0.0163 0.020 Uiso 1 1 calc R . .
C4 C 0.3337(2) 0.7394(2) -0.05324(12) 0.0184(3) Uani 1 1 d . . .
C5 C 0.2912(2) 0.5965(2) -0.05265(12) 0.0190(3) Uani 1 1 d . . .
H5 H 0.3334 0.5383 -0.1013 0.023 Uiso 1 1 calc R . .
C6 C 0.1846(2) 0.5397(2) 0.02125(12) 0.0175(3) Uani 1 1 d . . .
H6 H 0.1543 0.4419 0.0217 0.021 Uiso 1 1 calc R . .
C7 C 0.1214(2) 1.0000(2) 0.15567(14) 0.0233(4) Uani 1 1 d . . .
H7A H 0.2324 1.0122 0.1538 0.035 Uiso 1 1 calc R . .
H7B H 0.0647 1.0408 0.2110 0.035 Uiso 1 1 calc R . .
H7C H 0.0733 1.0583 0.0937 0.035 Uiso 1 1 calc R . .
C8 C 0.5184(2) 0.7190(2) -0.18895(14) 0.0257(4) Uani 1 1 d . . .
H8A H 0.5793 0.6214 -0.1526 0.039 Uiso 1 1 calc R . .
H8B H 0.5902 0.7800 -0.2321 0.039 Uiso 1 1 calc R . .
H8C H 0.4414 0.6943 -0.2290 0.039 Uiso 1 1 calc R . .
C9 C 0.0097(2) 0.55709(18) 0.17129(12) 0.0145(3) Uani 1 1 d . . .
C10 C -0.1323(2) 0.62904(19) 0.20536(12) 0.0154(3) Uani 1 1 d . . .
C11 C -0.4171(2) 0.8005(2) 0.16237(15) 0.0255(4) Uani 1 1 d . . .
H11A H -0.4804 0.8997 0.1279 0.031 Uiso 1 1 calc R . .
H11B H -0.4228 0.7189 0.1249 0.031 Uiso 1 1 calc R . .
C12 C -0.4890(2) 0.7542(2) 0.26432(16) 0.0285(4) Uani 1 1 d . . .
H12A H -0.5998 0.7432 0.2578 0.034 Uiso 1 1 calc R . .
H12B H -0.4918 0.8410 0.2990 0.034 Uiso 1 1 calc R . .
C13 C -0.2099(2) 0.52489(19) 0.27858(12) 0.0157(3) Uani 1 1 d . . .
C14 C -0.1247(2) 0.37527(19) 0.30021(12) 0.0154(3) Uani 1 1 d . . .
C15 C -0.1638(2) 0.23809(19) 0.37347(12) 0.0152(3) Uani 1 1 d . . .
C16 C -0.1557(2) 0.23168(19) 0.47525(12) 0.0156(3) Uani 1 1 d . . .
C17 C -0.1983(2) 0.10669(19) 0.54414(12) 0.0174(3) Uani 1 1 d . . .
H17 H -0.1946 0.1043 0.6126 0.021 Uiso 1 1 calc R . .
C18 C -0.2466(2) -0.01558(19) 0.51301(12) 0.0172(3) Uani 1 1 d . . .
C19 C -0.2505(2) -0.0152(2) 0.41320(13) 0.0180(3) Uani 1 1 d . . .
H19 H -0.2809 -0.0999 0.3920 0.022 Uiso 1 1 calc R . .
C20 C -0.2086(2) 0.11265(19) 0.34482(12) 0.0170(3) Uani 1 1 d . . .
H20 H -0.2109 0.1138 0.2764 0.020 Uiso 1 1 calc R . .
C21 C -0.0877(2) 0.3497(2) 0.60116(12) 0.0214(4) Uani 1 1 d . . .
H21A H -0.1923 0.3549 0.6347 0.032 Uiso 1 1 calc R . .
H21B H -0.0410 0.4392 0.6081 0.032 Uiso 1 1 calc R . .
H21C H -0.0194 0.2520 0.6308 0.032 Uiso 1 1 calc R . .
C22 C -0.3372(2) -0.2595(2) 0.55913(14) 0.0256(4) Uani 1 1 d . . .
H22A H -0.4358 -0.2212 0.5239 0.038 Uiso 1 1 calc R . .
H22B H -0.3551 -0.3388 0.6182 0.038 Uiso 1 1 calc R . .
H22C H -0.2558 -0.3060 0.5159 0.038 Uiso 1 1 calc R . .
O1 O 0.11245(15) 0.83773(14) 0.16796(9) 0.0181(3) Uani 1 1 d . . .
O2 O 0.43720(16) 0.80815(16) -0.12071(9) 0.0248(3) Uani 1 1 d . . .
O3 O -0.10313(16) 0.35403(14) 0.49905(9) 0.0209(3) Uani 1 1 d . . .
O4 O -0.28632(17) -0.13193(15) 0.58749(9) 0.0232(3) Uani 1 1 d . . .
S1 S 0.05122(5) 0.36400(5) 0.23229(3) 0.01621(13) Uani 1 1 d . . .
S2 S -0.21430(5) 0.82592(5) 0.16199(3) 0.02087(14) Uani 1 1 d . . .
S3 S -0.39022(6) 0.57427(6) 0.34163(4) 0.02712(15) 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 C6 1.391(2) . ?
C1 C2 1.406(2) . ?
C1 C9 1.475(2) . ?
C2 O1 1.368(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 O2 1.367(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.429(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.427(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.372(2) . ?
C9 S1 1.7225(16) . ?
C10 C13 1.432(2) . ?
C10 S2 1.7499(17) . ?
C11 C12 1.505(3) . ?
C11 S2 1.8021(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 S3 1.820(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.375(2) . ?
C13 S3 1.7550(17) . ?
C14 C15 1.480(2) . ?
C14 S1 1.7214(17) . ?
C15 C20 1.387(2) . ?
C15 C16 1.409(2) . ?
C16 O3 1.362(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 O4 1.3653(19) . ?
C18 C19 1.389(2) . ?
C19 C20 1.396(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O3 1.426(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O4 1.426(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C6 C1 C2 117.59(14) . . ?
C6 C1 C9 120.83(14) . . ?
C2 C1 C9 121.57(15) . . ?
O1 C2 C3 122.89(14) . . ?
O1 C2 C1 116.20(14) . . ?
C3 C2 C1 120.85(15) . . ?
C2 C3 C4 119.99(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O2 C4 C5 124.52(16) . . ?
O2 C4 C3 114.72(15) . . ?
C5 C4 C3 120.76(15) . . ?
C4 C5 C6 118.42(16) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 122.36(15) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 129.68(15) . . ?
C10 C9 S1 110.43(12) . . ?
C1 C9 S1 119.89(12) . . ?
C9 C10 C13 112.97(15) . . ?
C9 C10 S2 123.99(12) . . ?
C13 C10 S2 123.01(13) . . ?
C12 C11 S2 113.52(14) . . ?
C12 C11 H11A 108.9 . . ?
S2 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
S2 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 S3 116.41(14) . . ?
C11 C12 H12A 108.2 . . ?
S3 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
S3 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C14 C13 C10 112.92(15) . . ?
C14 C13 S3 120.63(13) . . ?
C10 C13 S3 126.40(13) . . ?
C13 C14 C15 128.49(15) . . ?
C13 C14 S1 110.39(12) . . ?
C15 C14 S1 121.06(13) . . ?
C20 C15 C16 118.07(14) . . ?
C20 C15 C14 121.61(15) . . ?
C16 C15 C14 120.32(14) . . ?
O3 C16 C17 123.87(15) . . ?
O3 C16 C15 115.58(14) . . ?
C17 C16 C15 120.55(15) . . ?
C16 C17 C18 119.95(15) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O4 C18 C19 124.45(15) . . ?
O4 C18 C17 114.72(15) . . ?
C19 C18 C17 120.83(15) . . ?
C18 C19 C20 118.37(15) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C15 C20 C19 122.17(15) . . ?
C15 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 O1 C7 117.73(13) . . ?
C4 O2 C8 117.43(14) . . ?
C16 O3 C21 117.50(13) . . ?
C18 O4 C22 116.73(14) . . ?
C14 S1 C9 93.23(8) . . ?
C10 S2 C11 97.49(8) . . ?
C13 S3 C12 104.98(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.956
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.956
_refine_diff_density_max    0.567
_refine_diff_density_min   -0.516
_refine_diff_density_rms    0.072
