data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Mimi Hii
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C15 H20 O5 S'
_chemical_absolute_configuration  ad
_chemical_formula_sum
 'C15 H20 O5 S'
_chemical_formula_weight          312.37
 
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
_symmetry_space_group_name_hall   'P 2yb'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.4663(2)
_cell_length_b                    17.8280(12)
_cell_length_c                    8.1473(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.423(3)
_cell_angle_gamma                 90.00
_cell_volume                      793.96(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6255
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.307
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              332
_exptl_absorpt_coefficient_mu     0.222
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9365
_exptl_absorpt_correction_T_max   0.9782
_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          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7744
_diffrn_reflns_av_R_equivalents   0.0593
_diffrn_reflns_av_sigmaI/netI     0.0522
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.39
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2685
_reflns_number_gt                 2315
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.1298P)²+0.0764P] 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        0.024(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.13(10)
_refine_ls_number_reflns          2685
_refine_ls_number_parameters      194
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0538
_refine_ls_R_factor_gt            0.0418
_refine_ls_wR_factor_ref          0.1301
_refine_ls_wR_factor_gt           0.1167
_refine_ls_goodness_of_fit_ref    0.761
_refine_ls_restrained_S_all       0.761
_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 0.66704(13) 0.77227(5) 0.99731(9) 0.0447(3) Uani 1 1 d . . .
O3 O 0.4624(4) 0.74059(12) 0.8801(2) 0.0381(5) Uani 1 1 d . . .
O2 O 0.3877(4) 0.63103(13) 0.6376(2) 0.0369(5) Uani 1 1 d . . .
C14 C 0.6009(5) 0.77872(19) 1.3252(4) 0.0387(7) Uani 1 1 d . . .
H14 H 0.7420 0.7478 1.3334 0.046 Uiso 1 1 calc R . .
C9 C 0.5100(5) 0.79983(17) 1.1737(3) 0.0303(6) Uani 1 1 d . . .
C11 C 0.1904(6) 0.86768(18) 1.3013(4) 0.0399(8) Uani 1 1 d . . .
H11 H 0.0483 0.8982 1.2930 0.048 Uiso 1 1 calc R . .
C12 C 0.2774(6) 0.84774(17) 1.4542(4) 0.0348(7) Uani 1 1 d . . .
O4 O 0.8313(4) 0.71302(18) 1.0394(3) 0.0635(9) Uani 1 1 d . . .
O1 O 0.1139(4) 0.53706(13) 0.6227(3) 0.0481(6) Uani 1 1 d . . .
C8 C 0.3570(6) 0.66752(18) 0.9154(4) 0.0356(7) Uani 1 1 d . . .
H8A H 0.2462 0.6704 1.0107 0.043 Uiso 1 1 calc R . .
H8B H 0.4871 0.6304 0.9394 0.043 Uiso 1 1 calc R . .
C15 C 0.1504(7) 0.8740(2) 1.6067(5) 0.0523(9) Uani 1 1 d . . .
H15A H 0.0724 0.9226 1.5856 0.078 Uiso 1 1 calc R . .
H15B H 0.2703 0.8792 1.6960 0.078 Uiso 1 1 calc R . .
H15C H 0.0257 0.8373 1.6379 0.078 Uiso 1 1 calc R . .
C13 C 0.4840(6) 0.80307(19) 1.4640(4) 0.0394(7) Uani 1 1 d . . .
H13 H 0.5463 0.7890 1.5687 0.047 Uiso 1 1 calc R . .
C7 C 0.2190(5) 0.64639(17) 0.7642(4) 0.0311(6) Uani 1 1 d . . .
H7 H 0.1113 0.6891 0.7301 0.037 Uiso 1 1 calc R . .
C10 C 0.3055(6) 0.8443(2) 1.1590(4) 0.0401(8) Uani 1 1 d . . .
H10 H 0.2445 0.8587 1.0542 0.048 Uiso 1 1 calc R . .
C3 C 0.0641(5) 0.57357(17) 0.7741(4) 0.0355(7) Uani 1 1 d . . .
H3 H -0.1136 0.5866 0.7798 0.043 Uiso 1 1 calc R . .
O5 O 0.7567(5) 0.83574(19) 0.9131(3) 0.0709(9) Uani 1 1 d . . .
C4 C 0.2623(6) 0.58342(19) 0.5241(4) 0.0368(7) Uani 1 1 d . . .
C6 C 0.1002(8) 0.6286(2) 0.4093(5) 0.0539(9) Uani 1 1 d . . .
H6A H 0.0226 0.5950 0.3293 0.081 Uiso 1 1 calc R . .
H6B H 0.1995 0.6659 0.3515 0.081 Uiso 1 1 calc R . .
H6C H -0.0262 0.6543 0.4729 0.081 Uiso 1 1 calc R . .
C1 C -0.0150(10) 0.5051(2) 1.0323(5) 0.0669(12) Uani 1 1 d . . .
H1A H -0.1730 0.5271 1.0377 0.080 Uiso 1 1 calc R . .
H1B H 0.0377 0.4714 1.1156 0.080 Uiso 1 1 calc R . .
C2 C 0.1298(8) 0.5213(2) 0.9105(5) 0.0517(9) Uani 1 1 d . . .
H2 H 0.2867 0.4984 0.9087 0.062 Uiso 1 1 calc R . .
C5 C 0.4473(7) 0.5366(3) 0.4366(5) 0.0629(12) Uani 1 1 d . . .
H5A H 0.5553 0.5123 0.5171 0.094 Uiso 1 1 calc R . .
H5B H 0.5446 0.5686 0.3643 0.094 Uiso 1 1 calc R . .
H5C H 0.3633 0.4982 0.3711 0.094 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 O5 1.413(3) . ?
S1 O4 1.427(3) . ?
S1 O3 1.571(2) . ?
S1 C9 1.749(3) . ?
O3 C8 1.454(4) . ?
O2 C7 1.415(3) . ?
O2 C4 1.427(4) . ?
C14 C13 1.373(4) . ?
C14 C9 1.380(4) . ?
C9 C10 1.375(4) . ?
C11 C12 1.377(5) . ?
C11 C10 1.386(4) . ?
C12 C13 1.384(5) . ?
C12 C15 1.502(4) . ?
O1 C4 1.413(4) . ?
O1 C3 1.423(4) . ?
C8 C7 1.488(4) . ?
C7 C3 1.552(4) . ?
C3 C2 1.493(5) . ?
C4 C5 1.496(5) . ?
C4 C6 1.516(5) . ?
C1 C2 1.306(6) . ?
 
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
O5 S1 O4 119.31(19) . . ?
O5 S1 O3 103.93(15) . . ?
O4 S1 O3 108.90(13) . . ?
O5 S1 C9 110.37(16) . . ?
O4 S1 C9 108.82(15) . . ?
O3 S1 C9 104.40(12) . . ?
C8 O3 S1 118.91(19) . . ?
C7 O2 C4 105.9(2) . . ?
C13 C14 C9 119.0(3) . . ?
C10 C9 C14 121.5(3) . . ?
C10 C9 S1 119.6(2) . . ?
C14 C9 S1 118.9(2) . . ?
C12 C11 C10 121.5(3) . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 C15 120.6(3) . . ?
C13 C12 C15 120.9(3) . . ?
C4 O1 C3 109.8(2) . . ?
O3 C8 C7 105.2(2) . . ?
C14 C13 C12 121.3(3) . . ?
O2 C7 C8 108.8(2) . . ?
O2 C7 C3 103.6(2) . . ?
C8 C7 C3 116.2(2) . . ?
C9 C10 C11 118.3(3) . . ?
O1 C3 C2 108.3(3) . . ?
O1 C3 C7 103.3(2) . . ?
C2 C3 C7 115.6(3) . . ?
O1 C4 O2 104.8(2) . . ?
O1 C4 C5 109.7(3) . . ?
O2 C4 C5 108.5(3) . . ?
O1 C4 C6 109.1(3) . . ?
O2 C4 C6 111.1(3) . . ?
C5 C4 C6 113.4(3) . . ?
C1 C2 C3 124.0(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.208
_refine_diff_density_min   -0.233
_refine_diff_density_rms    0.041
