# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_130703b
_database_code_depnum_ccdc_archive 'CCDC 952617'
_audit_update_record             
;
2013-07-26 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 O8 S'
_chemical_formula_weight         358.35

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.5675(5)
_cell_length_b                   7.6532(8)
_cell_length_c                   45.491(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1590.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2326
_cell_measurement_theta_min      2.808
_cell_measurement_theta_max      22.65

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7980
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2790
_reflns_number_gt                2222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0320P)²+1.4491P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(15)
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 1.1853(6) 0.4982(4) 0.94241(5) 0.0445(7) Uani 1 1 d . . .
O2 O 1.0403(7) -0.0246(4) 0.95010(6) 0.0559(8) Uani 1 1 d . . .
O3 O 1.4045(8) -0.0771(3) 0.90708(6) 0.0486(8) Uani 1 1 d . . .
H3 H 1.2896 -0.1009 0.9203 0.073 Uiso 1 1 calc R . .
O4 O 1.8675(7) 0.4099(3) 0.86532(6) 0.0396(7) Uani 1 1 d . . .
O5 O 1.5063(8) 0.4542(4) 0.75876(6) 0.0593(9) Uani 1 1 d . . .
O6 O 1.3957(8) 0.5334(4) 0.80433(6) 0.0587(9) Uani 1 1 d . . .
H6 H 1.3181 0.6164 0.7960 0.088 Uiso 1 1 calc R . .
O7 O 1.8243(6) 0.1769(3) 0.77747(6) 0.0427(7) Uani 1 1 d . . .
H7 H 1.7060 0.1331 0.7661 0.064 Uiso 1 1 calc R . .
O8 O 1.0706(10) 0.7788(4) 0.78503(7) 0.0858(13) Uani 1 1 d . . .
H8C H 1.0480 0.7645 0.7666 0.103 Uiso 1 1 d R . .
H8D H 0.9205 0.8301 0.7919 0.103 Uiso 1 1 d R . .
S1 S 1.5831(2) -0.02551(12) 0.83341(2) 0.0399(3) Uani 1 1 d . . .
C1 C 0.9952(10) 0.4336(6) 0.96278(9) 0.0466(11) Uani 1 1 d . . .
C2 C 0.9415(10) 0.2634(5) 0.96569(9) 0.0469(11) Uani 1 1 d . . .
H2 H 0.8087 0.2256 0.9798 0.056 Uiso 1 1 calc R . .
C3 C 1.0866(10) 0.1364(5) 0.94720(8) 0.0411(10) Uani 1 1 d . . .
C4 C 1.2849(9) 0.2055(5) 0.92583(8) 0.0339(10) Uani 1 1 d . . .
C5 C 1.4426(10) 0.0987(5) 0.90582(9) 0.0362(10) Uani 1 1 d . . .
C6 C 1.6314(9) 0.1686(4) 0.88557(7) 0.0296(9) Uani 1 1 d . . .
C7 C 1.6702(9) 0.3515(5) 0.88520(8) 0.0320(9) Uani 1 1 d . . .
C8 C 1.5221(8) 0.4601(5) 0.90422(7) 0.0337(9) Uani 1 1 d . . .
H8 H 1.5514 0.5803 0.9038 0.040 Uiso 1 1 calc R . .
C9 C 1.3286(9) 0.3858(5) 0.92402(8) 0.0350(10) Uani 1 1 d . . .
C10 C 0.8623(13) 0.5782(6) 0.97994(10) 0.0657(15) Uani 1 1 d . . .
H10A H 0.7069 0.5330 0.9919 0.099 Uiso 1 1 calc R . .
H10B H 0.7853 0.6645 0.9667 0.099 Uiso 1 1 calc R . .
H10C H 1.0087 0.6306 0.9922 0.099 Uiso 1 1 calc R . .
C11 C 1.7965(9) 0.0547(5) 0.86460(9) 0.0395(10) Uani 1 1 d . . .
H11A H 1.8726 -0.0450 0.8753 0.047 Uiso 1 1 calc R . .
H11B H 1.9626 0.1199 0.8571 0.047 Uiso 1 1 calc R . .
C12 C 1.9116(12) 0.5937(5) 0.86320(10) 0.0491(12) Uani 1 1 d . . .
H12A H 1.7290 0.6498 0.8587 0.074 Uiso 1 1 calc R . .
H12B H 2.0504 0.6180 0.8479 0.074 Uiso 1 1 calc R . .
H12C H 1.9850 0.6372 0.8816 0.074 Uiso 1 1 calc R . .
C13 C 1.5201(9) 0.4315(5) 0.78471(9) 0.0376(10) Uani 1 1 d . . .
C14 C 1.6742(9) 0.2766(5) 0.79870(8) 0.0329(9) Uani 1 1 d . . .
H14 H 1.8198 0.3225 0.8125 0.039 Uiso 1 1 calc R . .
C15 C 1.4512(9) 0.1712(5) 0.81640(8) 0.0366(9) Uani 1 1 d . . .
H15A H 1.2906 0.1404 0.8034 0.044 Uiso 1 1 calc R . .
H15B H 1.3724 0.2462 0.8317 0.044 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
O1 C1 1.362(5) . ?
O1 C9 1.367(4) . ?
O2 C3 1.257(5) . ?
O3 C5 1.358(4) . ?
O3 H3 0.8200 . ?
O4 C7 1.353(5) . ?
O4 C12 1.425(4) . ?
O5 C13 1.194(4) . ?
O6 C13 1.315(4) . ?
O6 H6 0.8200 . ?
O7 C14 1.409(4) . ?
O7 H7 0.8200 . ?
O8 H8C 0.8500 . ?
O8 H8D 0.8500 . ?
S1 C15 1.797(4) . ?
S1 C11 1.827(4) . ?
C1 C2 1.332(6) . ?
C1 C10 1.484(6) . ?
C2 C3 1.446(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.430(6) . ?
C4 C9 1.397(5) . ?
C4 C5 1.420(5) . ?
C5 C6 1.370(5) . ?
C6 C7 1.412(5) . ?
C6 C11 1.496(5) . ?
C7 C8 1.377(5) . ?
C8 C9 1.384(5) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.519(5) . ?
C14 C15 1.529(5) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C1 O1 C9 119.6(3) . . ?
C5 O3 H3 109.5 . . ?
C7 O4 C12 117.7(3) . . ?
C13 O6 H6 109.5 . . ?
C14 O7 H7 109.5 . . ?
H8C O8 H8D 108.9 . . ?
C15 S1 C11 103.41(19) . . ?
C2 C1 O1 122.6(4) . . ?
C2 C1 C10 127.0(4) . . ?
O1 C1 C10 110.4(4) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
O2 C3 C4 122.7(4) . . ?
O2 C3 C2 121.4(4) . . ?
C4 C3 C2 115.9(4) . . ?
C9 C4 C5 117.3(4) . . ?
C9 C4 C3 119.7(4) . . ?
C5 C4 C3 123.0(4) . . ?
O3 C5 C6 119.7(4) . . ?
O3 C5 C4 118.6(4) . . ?
C6 C5 C4 121.7(3) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C11 121.2(3) . . ?
C7 C6 C11 120.5(4) . . ?
O4 C7 C8 123.3(3) . . ?
O4 C7 C6 114.8(3) . . ?
C8 C7 C6 122.0(4) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C8 116.5(3) . . ?
O1 C9 C4 121.1(4) . . ?
C8 C9 C4 122.4(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 S1 115.0(3) . . ?
C6 C11 H11A 108.5 . . ?
S1 C11 H11A 108.5 . . ?
C6 C11 H11B 108.5 . . ?
S1 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 124.2(4) . . ?
O5 C13 C14 123.5(4) . . ?
O6 C13 C14 112.3(3) . . ?
O7 C14 C13 111.2(3) . . ?
O7 C14 C15 113.5(3) . . ?
C13 C14 C15 108.9(3) . . ?
O7 C14 H14 107.7 . . ?
C13 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C14 C15 S1 116.5(3) . . ?
C14 C15 H15A 108.2 . . ?
S1 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
S1 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C2 0.0(6) . . . . ?
C9 O1 C1 C10 -179.2(4) . . . . ?
O1 C1 C2 C3 0.5(7) . . . . ?
C10 C1 C2 C3 179.6(5) . . . . ?
C1 C2 C3 O2 178.9(4) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
O2 C3 C4 C9 -179.3(4) . . . . ?
C2 C3 C4 C9 0.4(6) . . . . ?
O2 C3 C4 C5 1.0(7) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C9 C4 C5 O3 180.0(4) . . . . ?
C3 C4 C5 O3 -0.3(6) . . . . ?
C9 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 C6 -179.9(4) . . . . ?
O3 C5 C6 C7 -178.8(4) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
O3 C5 C6 C11 0.3(6) . . . . ?
C4 C5 C6 C11 180.0(4) . . . . ?
C12 O4 C7 C8 -3.2(6) . . . . ?
C12 O4 C7 C6 178.3(4) . . . . ?
C5 C6 C7 O4 177.8(3) . . . . ?
C11 C6 C7 O4 -1.4(5) . . . . ?
C5 C6 C7 C8 -0.8(6) . . . . ?
C11 C6 C7 C8 -179.9(3) . . . . ?
O4 C7 C8 C9 -178.9(4) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C1 O1 C9 C8 -178.9(4) . . . . ?
C1 O1 C9 C4 -0.4(5) . . . . ?
C7 C8 C9 O1 -179.7(3) . . . . ?
C7 C8 C9 C4 1.7(6) . . . . ?
C5 C4 C9 O1 179.9(3) . . . . ?
C3 C4 C9 O1 0.1(6) . . . . ?
C5 C4 C9 C8 -1.6(6) . . . . ?
C3 C4 C9 C8 178.6(4) . . . . ?
C5 C6 C11 S1 77.8(4) . . . . ?
C7 C6 C11 S1 -103.1(4) . . . . ?
C15 S1 C11 C6 57.0(3) . . . . ?
O5 C13 C14 O7 6.8(6) . . . . ?
O6 C13 C14 O7 -175.5(3) . . . . ?
O5 C13 C14 C15 -119.1(4) . . . . ?
O6 C13 C14 C15 58.7(4) . . . . ?
O7 C14 C15 S1 52.5(4) . . . . ?
C13 C14 C15 S1 176.9(3) . . . . ?
C11 S1 C15 C14 74.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052
