# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1817479'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Mar 30 2012 14:54:36, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H16 O5 S'
_chemical_formula_sum            'C10 H16 O5 S'
_chemical_formula_weight         248.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.457(2)
_cell_length_b                   10.698(5)
_cell_length_c                   21.399(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1249.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6442
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.69
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ab
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9757
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.90
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2450
_reflns_number_total             2548
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.225
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1026
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 1.01099(8) 0.66993(4) 0.249545(19) 0.03151(14) Uani 1 1 d . . .
O1 O 1.1901(3) 0.72057(14) 0.36912(6) 0.0449(4) Uani 1 1 d . . .
O2 O 0.9636(3) 0.58572(13) 0.42569(6) 0.0439(4) Uani 1 1 d . . .
O3 O 0.6283(3) 0.46563(13) 0.26294(6) 0.0406(3) Uani 1 1 d . . .
O4 O 0.8014(3) 0.32210(12) 0.37933(7) 0.0461(4) Uani 1 1 d . . .
O5 O 0.4794(3) 0.44914(13) 0.39681(6) 0.0390(3) Uani 1 1 d . . .
C1 C 1.1025(4) 0.5504(2) 0.19600(9) 0.0424(5) Uani 1 1 d . . .
H1A H 0.9709 0.4918 0.1907 0.064 Uiso 1 1 calc R . .
H1B H 1.2438 0.5078 0.2121 0.064 Uiso 1 1 calc R . .
H1C H 1.1421 0.5874 0.1564 0.064 Uiso 1 1 calc R . .
C2 C 0.7395(4) 0.7283(2) 0.21179(11) 0.0486(5) Uani 1 1 d . . .
H2A H 0.7852 0.7786 0.1765 0.073 Uiso 1 1 calc R . .
H2B H 0.6475 0.7782 0.2408 0.073 Uiso 1 1 calc R . .
H2C H 0.6409 0.6594 0.1979 0.073 Uiso 1 1 calc R . .
C3 C 1.4882(6) 0.8607(2) 0.40772(12) 0.0608(6) Uani 1 1 d . . .
H3A H 1.6019 0.8291 0.3774 0.091 Uiso 1 1 calc R . .
H3B H 1.5760 0.8882 0.4441 0.091 Uiso 1 1 calc R . .
H3C H 1.3992 0.9297 0.3902 0.091 Uiso 1 1 calc R . .
C4 C 1.3143(5) 0.7604(2) 0.42552(9) 0.0502(5) Uani 1 1 d . . .
H4A H 1.4018 0.6907 0.4441 0.060 Uiso 1 1 calc R . .
H4B H 1.1966 0.7916 0.4557 0.060 Uiso 1 1 calc R . .
C5 C 1.0209(3) 0.62900(16) 0.37533(8) 0.0320(4) Uani 1 1 d . . .
C6 C 0.9149(3) 0.59217(17) 0.31614(8) 0.0310(4) Uani 1 1 d . . .
C7 C 0.7384(3) 0.49698(16) 0.31135(8) 0.0294(4) Uani 1 1 d . . .
C8 C 0.6844(3) 0.41494(16) 0.36828(8) 0.0302(4) Uani 1 1 d . . .
C9 C 0.3968(4) 0.3710(2) 0.44868(10) 0.0490(5) Uani 1 1 d . . .
H9A H 0.4384 0.2845 0.4403 0.059 Uiso 1 1 calc R . .
H9B H 0.2201 0.3769 0.4525 0.059 Uiso 1 1 calc R . .
C10 C 0.5130(7) 0.4110(2) 0.50833(11) 0.0657(7) Uani 1 1 d . . .
H10A H 0.6880 0.4106 0.5037 0.099 Uiso 1 1 calc R . .
H10B H 0.4670 0.3543 0.5411 0.099 Uiso 1 1 calc R . .
H10C H 0.4590 0.4938 0.5187 0.099 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0332(2) 0.0331(2) 0.0283(2) 0.00496(15) -0.00075(17) -0.00642(16)
O1 0.0582(9) 0.0467(7) 0.0300(6) 0.0019(6) -0.0072(7) -0.0238(7)
O2 0.0505(8) 0.0542(8) 0.0270(6) 0.0019(6) 0.0016(6) -0.0152(7)
O3 0.0430(7) 0.0448(7) 0.0340(7) 0.0030(5) -0.0077(6) -0.0147(6)
O4 0.0551(9) 0.0360(7) 0.0472(8) 0.0090(6) 0.0076(7) 0.0108(7)
O5 0.0337(6) 0.0434(7) 0.0398(7) 0.0113(6) 0.0096(6) 0.0015(6)
C1 0.0434(10) 0.0486(11) 0.0352(9) 0.0029(8) 0.0077(8) 0.0083(9)
C2 0.0428(10) 0.0471(11) 0.0560(12) 0.0189(10) -0.0002(10) 0.0120(10)
C3 0.0639(15) 0.0647(14) 0.0539(13) -0.0050(11) -0.0112(12) -0.0251(14)
C4 0.0664(14) 0.0508(11) 0.0334(10) -0.0047(9) -0.0122(10) -0.0205(11)
C5 0.0329(8) 0.0325(8) 0.0305(8) -0.0010(7) -0.0003(7) -0.0047(7)
C6 0.0347(8) 0.0330(8) 0.0253(8) 0.0024(7) 0.0007(6) -0.0067(7)
C7 0.0294(8) 0.0299(8) 0.0288(8) 0.0027(7) 0.0006(6) -0.0009(7)
C8 0.0298(8) 0.0295(8) 0.0312(8) 0.0015(7) -0.0009(7) -0.0034(7)
C9 0.0428(11) 0.0573(12) 0.0468(12) 0.0161(10) 0.0128(9) -0.0068(10)
C10 0.094(2) 0.0626(14) 0.0406(12) 0.0091(10) 0.0108(13) 0.0060(18)

_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 C1 1.788(2) . ?
S1 C2 1.799(2) . ?
S1 C6 1.7314(18) . ?
O1 C4 1.448(2) . ?
O1 C5 1.353(2) . ?
O2 C5 1.214(2) . ?
O3 C7 1.244(2) . ?
O4 C8 1.204(2) . ?
O5 C8 1.326(2) . ?
O5 C9 1.461(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.482(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.447(2) . ?
C6 C7 1.405(2) . ?
C7 C8 1.530(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.488(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 S1 C2 100.98(12) . . ?
C6 S1 C1 105.57(9) . . ?
C6 S1 C2 106.67(10) . . ?
C5 O1 C4 116.77(15) . . ?
C8 O5 C9 116.90(15) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O1 C4 C3 107.35(17) . . ?
O1 C4 H4A 110.2 . . ?
O1 C4 H4B 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
O1 C5 C6 112.58(14) . . ?
O2 C5 O1 122.63(16) . . ?
O2 C5 C6 124.77(16) . . ?
C5 C6 S1 117.94(13) . . ?
C7 C6 S1 119.72(13) . . ?
C7 C6 C5 122.35(15) . . ?
O3 C7 C6 125.97(16) . . ?
O3 C7 C8 114.53(15) . . ?
C6 C7 C8 119.32(15) . . ?
O4 C8 O5 125.76(17) . . ?
O4 C8 C7 121.83(17) . . ?
O5 C8 C7 111.78(15) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
O5 C9 C10 110.9(2) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
S1 C6 C7 O3 -4.6(3) . . . . ?
S1 C6 C7 C8 170.33(13) . . . . ?
O1 C5 C6 S1 -1.4(2) . . . . ?
O1 C5 C6 C7 178.80(17) . . . . ?
O2 C5 C6 S1 177.11(17) . . . . ?
O2 C5 C6 C7 -2.7(3) . . . . ?
O3 C7 C8 O4 88.4(2) . . . . ?
O3 C7 C8 O5 -82.9(2) . . . . ?
C1 S1 C6 C5 127.50(16) . . . . ?
C1 S1 C6 C7 -52.72(18) . . . . ?
C2 S1 C6 C5 -125.65(17) . . . . ?
C2 S1 C6 C7 54.13(18) . . . . ?
C4 O1 C5 O2 3.9(3) . . . . ?
C4 O1 C5 C6 -177.53(18) . . . . ?
C5 O1 C4 C3 -179.7(2) . . . . ?
C5 C6 C7 O3 175.21(19) . . . . ?
C5 C6 C7 C8 -9.9(3) . . . . ?
C6 C7 C8 O4 -87.1(2) . . . . ?
C6 C7 C8 O5 101.60(19) . . . . ?
C8 O5 C9 C10 86.8(2) . . . . ?
C9 O5 C8 O4 3.9(3) . . . . ?
C9 O5 C8 C7 174.82(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
