 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H16 O6 S'
_chemical_formula_weight          288.31
 
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    P21/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                    10.9623(4)
_cell_length_b                    10.1397(4)
_cell_length_c                    11.9175(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.078(2)
_cell_angle_gamma                 90.00
_cell_volume                      1323.81(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     6502
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       34.97
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.447
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              608
_exptl_absorpt_coefficient_mu     0.264
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9564
_exptl_absorpt_correction_T_max   0.9839
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source                  
'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator    'graphite'
_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             7489
_diffrn_reflns_av_R_equivalents   0.0314
_diffrn_reflns_av_sigmaI/netI     0.0441
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.19
_diffrn_reflns_theta_max          26.00
_reflns_number_total              2572
_reflns_number_gt                 2051
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_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)+(0.0001P)²+0.8020P] 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        0.0109(13)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2572
_refine_ls_number_parameters      189
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0522
_refine_ls_R_factor_gt            0.0384
_refine_ls_wR_factor_ref          0.0830
_refine_ls_wR_factor_gt           0.0786
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_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
S1 S 0.51487(4) 0.13123(5) 0.15251(4) 0.03509(16) Uani 1 1 d . . .
O1 O 0.55341(13) 0.21369(14) 0.24524(12) 0.0492(4) Uani 1 1 d . . .
O3 O 0.42965(12) 0.00930(13) 0.39092(10) 0.0384(4) Uani 1 1 d . . .
O2 O 0.60365(12) 0.04477(16) 0.10522(12) 0.0489(4) Uani 1 1 d . . .
O4 O 0.25864(11) 0.11173(13) 0.33462(10) 0.0365(3) Uani 1 1 d . . .
O5 O 0.21852(11) -0.11637(11) 0.07154(10) 0.0292(3) Uani 1 1 d . . .
O6 O 0.13870(10) 0.05242(12) -0.02838(10) 0.0306(3) Uani 1 1 d . . .
C1 C 0.38224(15) 0.03537(17) 0.19151(13) 0.0237(4) Uani 1 1 d . . .
H1 H 0.3909 -0.0591 0.1690 0.033(5) Uiso 1 1 calc R . .
C3 C 0.30563(18) 0.23329(17) 0.08282(15) 0.0341(4) Uani 1 1 d . . .
H3 H 0.2518 0.2511 0.0150 0.031(5) Uiso 1 1 calc R . .
C2 C 0.26953(15) 0.09791(17) 0.13356(13) 0.0245(4) Uani 1 1 d . . .
C4 C 0.43726(18) 0.2267(2) 0.04759(16) 0.0399(5) Uani 1 1 d . . .
H4A H 0.4729 0.3163 0.0438 0.040(5) Uiso 1 1 calc R . .
H4B H 0.4424 0.1843 -0.0269 0.051(6) Uiso 1 1 calc R . .
C5 C 0.36394(16) 0.04730(17) 0.31581(14) 0.0288(4) Uani 1 1 d . . .
C6 C 0.18315(17) 0.1327(2) 0.23237(15) 0.0338(5) Uani 1 1 d . . .
C7 C 0.1605(2) 0.2801(2) 0.22130(18) 0.0520(6) Uani 1 1 d . . .
H7A H 0.0896 0.2980 0.1698 0.056(6) Uiso 1 1 calc R . .
H7B H 0.1453 0.3200 0.2953 0.074(8) Uiso 1 1 calc R . .
C8 C 0.2771(2) 0.33400(19) 0.17387(19) 0.0510(6) Uani 1 1 d . . .
H8A H 0.3436 0.3381 0.2322 0.054(6) Uiso 1 1 calc R . .
H8B H 0.2641 0.4230 0.1415 0.069(7) Uiso 1 1 calc R . .
C9 C 0.07093(18) 0.0482(3) 0.24392(17) 0.0479(6) Uani 1 1 d . . .
H9A H 0.0952 -0.0446 0.2508 0.049(6) Uiso 1 1 calc R . .
H9B H 0.0166 0.0594 0.1775 0.051(6) Uiso 1 1 calc R . .
H9C H 0.0281 0.0749 0.3111 0.073(8) Uiso 1 1 calc R . .
C10 C 0.20299(15) 0.01067(17) 0.04773(13) 0.0249(4) Uani 1 1 d . . .
C11 C 0.15521(18) -0.20898(18) -0.00314(16) 0.0360(5) Uani 1 1 d . . .
H11A H 0.1788 -0.1949 -0.0816 0.046(6) Uiso 1 1 calc R . .
H11B H 0.0657 -0.1978 0.0007 0.049(6) Uiso 1 1 calc R . .
C12 C 0.1925(2) -0.34367(19) 0.03614(19) 0.0434(5) Uani 1 1 d . . .
H12A H 0.1519 -0.4102 -0.0117 0.081(8) Uiso 1 1 calc R . .
H12B H 0.1689 -0.3559 0.1140 0.046(6) Uiso 1 1 calc R . .
H12C H 0.2812 -0.3531 0.0319 0.057(7) Uiso 1 1 calc R . .
 
 
_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
S1 O1 1.4370(14) . ?
S1 O2 1.4399(15) . ?
S1 C4 1.7741(19) . ?
S1 C1 1.8230(17) . ?
O3 C5 1.192(2) . ?
O4 C5 1.352(2) . ?
O4 C6 1.464(2) . ?
O5 C10 1.329(2) . ?
O5 C11 1.453(2) . ?
O6 C10 1.2052(19) . ?
C1 C5 1.507(2) . ?
C1 C2 1.531(2) . ?
C1 H1 1.0000 . ?
C3 C4 1.519(3) . ?
C3 C8 1.530(3) . ?
C3 C2 1.557(2) . ?
C3 H3 1.0000 . ?
C2 C10 1.519(2) . ?
C2 C6 1.578(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C9 1.510(3) . ?
C6 C7 1.520(3) . ?
C7 C8 1.518(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.496(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
O1 S1 O2 118.11(9) . . ?
O1 S1 C4 110.16(9) . . ?
O2 S1 C4 111.72(10) . . ?
O1 S1 C1 109.22(8) . . ?
O2 S1 C1 109.37(8) . . ?
C4 S1 C1 95.98(8) . . ?
C5 O4 C6 113.12(13) . . ?
C10 O5 C11 116.18(13) . . ?
C5 C1 C2 106.03(14) . . ?
C5 C1 S1 110.10(11) . . ?
C2 C1 S1 107.59(11) . . ?
C5 C1 H1 111.0 . . ?
C2 C1 H1 111.0 . . ?
S1 C1 H1 111.0 . . ?
C4 C3 C8 116.46(17) . . ?
C4 C3 C2 109.03(15) . . ?
C8 C3 C2 104.57(16) . . ?
C4 C3 H3 108.8 . . ?
C8 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C10 C2 C1 115.00(14) . . ?
C10 C2 C3 112.00(13) . . ?
C1 C2 C3 109.15(14) . . ?
C10 C2 C6 110.26(14) . . ?
C1 C2 C6 104.63(13) . . ?
C3 C2 C6 105.10(14) . . ?
C3 C4 S1 105.38(13) . . ?
C3 C4 H4A 110.7 . . ?
S1 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
S1 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
O3 C5 O4 121.86(16) . . ?
O3 C5 C1 127.85(17) . . ?
O4 C5 C1 110.28(14) . . ?
O4 C6 C9 106.23(16) . . ?
O4 C6 C7 107.51(15) . . ?
C9 C6 C7 115.80(18) . . ?
O4 C6 C2 104.61(13) . . ?
C9 C6 C2 117.01(16) . . ?
C7 C6 C2 104.82(17) . . ?
C8 C7 C6 104.43(16) . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C7 C8 C3 102.71(17) . . ?
C7 C8 H8A 111.2 . . ?
C3 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C3 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C10 O5 124.63(15) . . ?
O6 C10 C2 123.76(16) . . ?
O5 C10 C2 111.48(13) . . ?
O5 C11 C12 106.23(15) . . ?
O5 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
O5 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.984
_diffrn_reflns_theta_full              26.00
_diffrn_measured_fraction_theta_full   0.984
_refine_diff_density_max    0.237
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.045
