# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1811536'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 O5 S'
_chemical_formula_weight         236.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7445(3)
_cell_length_b                   7.5360(3)
_cell_length_c                   9.9477(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.123(4)
_cell_angle_gamma                90
_cell_volume                     580.17(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    1491
_cell_measurement_theta_min      3.2689
_cell_measurement_theta_max      31.3116

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_min  0.96124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.2060
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            2882
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.276
_diffrn_reflns_theta_max         29.066
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2427
_reflns_number_gt                2356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro 1.171.36.20 (Agilent Technologies, 2012)'
_computing_cell_refinement       
'CrysAlisPro 1.171.36.20 (Agilent Technologies, 2012)'
_computing_data_reduction        
'CrysAlisPro 1.171.36.20 (Agilent Technologies, 2012)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.0254P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.27(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2427
_refine_ls_number_parameters     158
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25054(6) 0.92180(7) 0.68367(5) 0.01875(14) Uani 1 1 d . . . . .
O1 O 0.2598(2) 1.0995(3) 0.62647(17) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.0863(2) 0.8375(3) 0.64284(16) 0.0243(4) Uani 1 1 d . . . . .
O3 O 0.3973(2) 0.8104(3) 0.65086(17) 0.0274(4) Uani 1 1 d . . . . .
C1 C 0.1022(3) 0.9093(4) 0.92639(19) 0.0188(4) Uani 1 1 d . . . . .
H1D H 0.006339 0.866286 0.877609 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0922(3) 0.9357(3) 1.0645(2) 0.0200(4) Uani 1 1 d . . . . .
C3 C 0.2384(3) 1.0002(3) 1.1360(2) 0.0212(5) Uani 1 1 d . . . . .
C4 C 0.3887(3) 1.0369(4) 1.0671(2) 0.0214(5) Uani 1 1 d . . . . .
H4A H 0.484590 1.080083 1.115674 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4010(3) 1.0115(3) 0.9290(2) 0.0193(4) Uani 1 1 d . . . . .
C6 C 0.2537(3) 0.9465(3) 0.8601(2) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.2360(3) 1.0294(4) 1.2858(2) 0.0291(6) Uani 1 1 d . . . . .
H7A H 0.348432 1.066769 1.318424 0.044 Uiso 1 1 calc R U . . .
H7B H 0.205446 0.920747 1.329254 0.044 Uiso 1 1 calc R U . . .
H7C H 0.152699 1.119344 1.305017 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5694(3) 1.0540(4) 0.8633(3) 0.0274(5) Uani 1 1 d . . . . .
H8A H 0.619039 0.946716 0.829985 0.041 Uiso 1 1 calc R U . . .
H8B H 0.648030 1.107452 0.928285 0.041 Uiso 1 1 calc R U . . .
H8C H 0.547726 1.134898 0.790065 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0725(3) 0.8954(4) 1.1347(2) 0.0278(6) Uani 1 1 d . . . . .
H9A H -0.118104 1.003018 1.170940 0.042 Uiso 1 1 calc R U . . .
H9B H -0.048848 0.812553 1.206295 0.042 Uiso 1 1 calc R U . . .
H9C H -0.155444 0.845079 1.071499 0.042 Uiso 1 1 calc R U . . .
OW1 O 0.1572(2) 0.5713(3) 0.45974(19) 0.0295(4) Uani 1 1 d D . . . .
HW1A H 0.254(7) 0.499(9) 0.480(7) 0.044 Uiso 0.5 1 d D U P . .
HW1B H 0.077(3) 0.492(4) 0.427(3) 0.044 Uiso 1 1 d D U . . .
HW1C H 0.124(4) 0.653(4) 0.524(3) 0.044 Uiso 1 1 d D U . . .
OW2 O 0.3964(2) 0.3843(3) 0.53878(19) 0.0301(5) Uani 1 1 d D . . . .
HW2A H 0.308(7) 0.464(8) 0.520(7) 0.045 Uiso 0.5 1 d D U P . .
HW2B H 0.366(4) 0.279(4) 0.579(3) 0.045 Uiso 1 1 d D U . . .
HW2C H 0.462(4) 0.352(5) 0.468(3) 0.045 Uiso 1 1 d D U . . .


_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 1.458(2) . ?
S1 O3 1.4596(18) . ?
S1 O2 1.4656(17) . ?
S1 C6 1.764(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 H1D 0.9300 . ?
C2 C3 1.402(3) . ?
C2 C9 1.508(3) . ?
C3 C4 1.400(3) . ?
C3 C7 1.507(3) . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(3) . ?
C5 C8 1.514(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
OW1 HW1A 0.94(2) . ?
OW1 HW1B 0.91(2) . ?
OW1 HW1C 0.93(2) . ?
OW2 HW2A 0.92(2) . ?
OW2 HW2B 0.92(2) . ?
OW2 HW2C 0.91(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
O1 S1 O3 113.03(11) . . ?
O1 S1 O2 110.16(11) . . ?
O3 S1 O2 111.32(11) . . ?
O1 S1 C6 106.99(11) . . ?
O3 S1 C6 107.51(10) . . ?
O2 S1 C6 107.54(10) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 H1D 119.5 . . ?
C6 C1 H1D 119.5 . . ?
C1 C2 C3 118.47(19) . . ?
C1 C2 C9 120.5(2) . . ?
C3 C2 C9 121.06(19) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 C7 119.8(2) . . ?
C2 C3 C7 120.9(2) . . ?
C5 C4 C3 123.0(2) . . ?
C5 C4 H4A 118.5 . . ?
C3 C4 H4A 118.5 . . ?
C4 C5 C6 116.57(19) . . ?
C4 C5 C8 119.2(2) . . ?
C6 C5 C8 124.2(2) . . ?
C1 C6 C5 121.6(2) . . ?
C1 C6 S1 117.91(16) . . ?
C5 C6 S1 120.43(16) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
HW1A OW1 HW1B 103(5) . . ?
HW1A OW1 HW1C 118(5) . . ?
HW1B OW1 HW1C 118(3) . . ?
HW2A OW2 HW2B 117(5) . . ?
HW2A OW2 HW2C 117(5) . . ?
HW2B OW2 HW2C 105(3) . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.062

