 
data_mp 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H20 O4 S2' 
_chemical_formula_weight          364.46 
 
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)/n 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    5.6850(4) 
_cell_length_b                    15.5496(13) 
_cell_length_c                    20.7033(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.1020(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1829.8(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     8622
_cell_measurement_theta_min       2.36 
_cell_measurement_theta_max       25.32 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.23 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.323 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              768 
_exptl_absorpt_coefficient_mu     0.309 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9323 
_exptl_absorpt_correction_T_max   0.9408 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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 APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             18211 
_diffrn_reflns_av_R_equivalents   0.0269 
_diffrn_reflns_av_sigmaI/netI     0.0182 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          1.64 
_diffrn_reflns_theta_max          25.37 
_reflns_number_total              3340 
_reflns_number_gt                 2804 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
 
_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)+(0.0898P)²+1.5464P] 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          3340 
_refine_ls_number_parameters      220 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0673 
_refine_ls_R_factor_gt            0.0578 
_refine_ls_wR_factor_ref          0.1709 
_refine_ls_wR_factor_gt           0.1613 
_refine_ls_goodness_of_fit_ref    1.055 
_refine_ls_restrained_S_all       1.055 
_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 
C1 C 0.6257(5) 0.61494(17) 0.28072(12) 0.0399(6) Uani 1 1 d . . . 
C2 C 0.7679(5) 0.6337(2) 0.22902(14) 0.0532(7) Uani 1 1 d . . . 
H2 H 0.9088 0.6632 0.2353 0.064 Uiso 1 1 calc R . . 
C3 C 0.6968(6) 0.6077(2) 0.16791(14) 0.0621(9) Uani 1 1 d . . . 
H3 H 0.7913 0.6203 0.1330 0.074 Uiso 1 1 calc R . . 
C4 C 0.4895(6) 0.5635(2) 0.15735(15) 0.0577(8) Uani 1 1 d . . . 
C5 C 0.3512(6) 0.5458(2) 0.20978(16) 0.0573(8) Uani 1 1 d . . . 
H5 H 0.2102 0.5164 0.2034 0.069 Uiso 1 1 calc R . . 
C6 C 0.4177(5) 0.57072(18) 0.27156(14) 0.0493(7) Uani 1 1 d . . . 
H6 H 0.3233 0.5578 0.3065 0.059 Uiso 1 1 calc R . . 
C7 C 0.4149(9) 0.5338(3) 0.09019(18) 0.0900(13) Uani 1 1 d . . . 
H7A H 0.3305 0.5792 0.0685 0.135 Uiso 1 1 calc R . . 
H7B H 0.3153 0.4843 0.0935 0.135 Uiso 1 1 calc R . . 
H7C H 0.5518 0.5193 0.0661 0.135 Uiso 1 1 calc R . . 
C8 C 0.5624(5) 0.74029(18) 0.38173(13) 0.0467(7) Uani 1 1 d . . . 
H8 H 0.3926 0.7313 0.3760 0.056 Uiso 1 1 calc R . . 
C9 C 0.6410(6) 0.8157(2) 0.33939(17) 0.0624(9) Uani 1 1 d . . . 
C10 C 0.5250(5) 0.83282(17) 0.27633(14) 0.0441(6) Uani 1 1 d . . . 
C11 C 0.3141(5) 0.79598(18) 0.25550(14) 0.0481(7) Uani 1 1 d . . . 
H11 H 0.2360 0.7579 0.2824 0.058 Uiso 1 1 calc R . . 
C12 C 0.2202(5) 0.8151(2) 0.19596(15) 0.0550(8) Uani 1 1 d . . . 
H12 H 0.0788 0.7900 0.1827 0.066 Uiso 1 1 calc R . . 
C13 C 0.3342(6) 0.87174(19) 0.15483(14) 0.0505(7) Uani 1 1 d . . . 
C14 C 0.5439(6) 0.90855(19) 0.17464(15) 0.0523(7) Uani 1 1 d . . . 
H14 H 0.6221 0.9462 0.1475 0.063 Uiso 1 1 calc R . . 
C15 C 0.6373(5) 0.88938(18) 0.23475(15) 0.0513(7) Uani 1 1 d . . . 
H15 H 0.7784 0.9147 0.2479 0.062 Uiso 1 1 calc R . . 
C16 C 0.3180(8) 0.9522(2) 0.05684(16) 0.0754(11) Uani 1 1 d . . . 
H16A H 0.3292 1.0053 0.0804 0.113 Uiso 1 1 calc R . . 
H16B H 0.2167 0.9598 0.0197 0.113 Uiso 1 1 calc R . . 
H16C H 0.4717 0.9353 0.0432 0.113 Uiso 1 1 calc R . . 
C17 C 0.6214(7) 0.7572(2) 0.45350(16) 0.0650(9) Uani 1 1 d . . . 
H17A H 0.7693 0.7882 0.4567 0.078 Uiso 1 1 calc R . . 
H17B H 0.6423 0.7026 0.4754 0.078 Uiso 1 1 calc R . . 
C18 C 0.2192(9) 0.7314(4) 0.5211(3) 0.1187(19) Uani 1 1 d . . . 
H18A H 0.1563 0.7006 0.4845 0.178 Uiso 1 1 calc R . . 
H18B H 0.0925 0.7539 0.5460 0.178 Uiso 1 1 calc R . . 
H18C H 0.3126 0.6931 0.5474 0.178 Uiso 1 1 calc R . . 
O1 O 0.9651(4) 0.66289(19) 0.35882(11) 0.0694(7) Uani 1 1 d . . . 
O2 O 0.6405(5) 0.57746(14) 0.40233(10) 0.0643(6) Uani 1 1 d . . . 
O3 O 0.8042(7) 0.8585(2) 0.35826(18) 0.1358(18) Uani 1 1 d . . . 
O4 O 0.2239(5) 0.88709(17) 0.09737(11) 0.0749(7) Uani 1 1 d . . . 
S1 S 0.71856(12) 0.64364(5) 0.35932(3) 0.0448(2) Uani 1 1 d . . . 
S2 S 0.3986(2) 0.81808(8) 0.49396(5) 0.0890(4) 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 1.378(4) . ? 
C1 C2 1.385(4) . ? 
C1 S1 1.759(3) . ? 
C2 C3 1.381(4) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.378(5) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.380(5) . ? 
C4 C7 1.517(4) . ? 
C5 C6 1.382(4) . ? 
C5 H5 0.9300 . ? 
C6 H6 0.9300 . ? 
C7 H7A 0.9600 . ? 
C7 H7B 0.9600 . ? 
C7 H7C 0.9600 . ? 
C8 C9 1.536(4) . ? 
C8 C17 1.540(4) . ? 
C8 S1 1.811(3) . ? 
C8 H8 0.9800 . ? 
C9 O3 1.201(4) . ? 
C9 C10 1.475(4) . ? 
C10 C11 1.390(4) . ? 
C10 C15 1.394(4) . ? 
C11 C12 1.366(4) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.394(4) . ? 
C12 H12 0.9300 . ? 
C13 O4 1.355(4) . ? 
C13 C14 1.378(4) . ? 
C14 C15 1.376(4) . ? 
C14 H14 0.9300 . ? 
C15 H15 0.9300 . ? 
C16 O4 1.426(4) . ? 
C16 H16A 0.9600 . ? 
C16 H16B 0.9600 . ? 
C16 H16C 0.9600 . ? 
C17 S2 1.801(4) . ? 
C17 H17A 0.9700 . ? 
C17 H17B 0.9700 . ? 
C18 S2 1.787(6) . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 0.9600 . ? 
O1 S1 1.434(2) . ? 
O2 S1 1.437(2) . ? 
 
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 120.7(3) . . ? 
C6 C1 S1 119.7(2) . . ? 
C2 C1 S1 119.5(2) . . ? 
C3 C2 C1 118.8(3) . . ? 
C3 C2 H2 120.6 . . ? 
C1 C2 H2 120.6 . . ? 
C4 C3 C2 121.7(3) . . ? 
C4 C3 H3 119.1 . . ? 
C2 C3 H3 119.1 . . ? 
C3 C4 C5 118.2(3) . . ? 
C3 C4 C7 121.3(3) . . ? 
C5 C4 C7 120.4(3) . . ? 
C4 C5 C6 121.5(3) . . ? 
C4 C5 H5 119.3 . . ? 
C6 C5 H5 119.3 . . ? 
C1 C6 C5 119.1(3) . . ? 
C1 C6 H6 120.5 . . ? 
C5 C6 H6 120.5 . . ? 
C4 C7 H7A 109.5 . . ? 
C4 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
C4 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
C9 C8 C17 111.1(3) . . ? 
C9 C8 S1 109.8(2) . . ? 
C17 C8 S1 106.9(2) . . ? 
C9 C8 H8 109.7 . . ? 
C17 C8 H8 109.7 . . ? 
S1 C8 H8 109.7 . . ? 
O3 C9 C10 121.1(3) . . ? 
O3 C9 C8 118.0(3) . . ? 
C10 C9 C8 120.8(3) . . ? 
C11 C10 C15 118.1(3) . . ? 
C11 C10 C9 124.6(3) . . ? 
C15 C10 C9 117.3(3) . . ? 
C12 C11 C10 120.6(3) . . ? 
C12 C11 H11 119.7 . . ? 
C10 C11 H11 119.7 . . ? 
C11 C12 C13 120.7(3) . . ? 
C11 C12 H12 119.6 . . ? 
C13 C12 H12 119.6 . . ? 
O4 C13 C14 124.8(3) . . ? 
O4 C13 C12 115.8(3) . . ? 
C14 C13 C12 119.4(3) . . ? 
C15 C14 C13 119.7(3) . . ? 
C15 C14 H14 120.1 . . ? 
C13 C14 H14 120.1 . . ? 
C14 C15 C10 121.5(3) . . ? 
C14 C15 H15 119.3 . . ? 
C10 C15 H15 119.3 . . ? 
O4 C16 H16A 109.5 . . ? 
O4 C16 H16B 109.5 . . ? 
H16A C16 H16B 109.5 . . ? 
O4 C16 H16C 109.5 . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 109.5 . . ? 
C8 C17 S2 113.4(2) . . ? 
C8 C17 H17A 108.9 . . ? 
S2 C17 H17A 108.9 . . ? 
C8 C17 H17B 108.9 . . ? 
S2 C17 H17B 108.9 . . ? 
H17A C17 H17B 107.7 . . ? 
S2 C18 H18A 109.5 . . ? 
S2 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
S2 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C13 O4 C16 118.0(3) . . ? 
O1 S1 O2 117.88(16) . . ? 
O1 S1 C1 108.82(13) . . ? 
O2 S1 C1 107.51(13) . . ? 
O1 S1 C8 108.23(15) . . ? 
O2 S1 C8 106.08(14) . . ? 
C1 S1 C8 107.92(13) . . ? 
C18 S2 C17 99.3(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.37 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    1.171 
_refine_diff_density_min   -0.704 
_refine_diff_density_rms    0.069 
