# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_V-21-000692
_database_code_depnum_ccdc_archive 'CCDC 2116804'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;OSU Crystallography Facility
United States of America
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_database_code_CSD               1G5KSP01
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            VRT-2433340
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 O4 S'
_chemical_formula_sum            'C13 H14 O4 S'
_chemical_formula_weight         266.30
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6416(9)
_cell_length_b                   6.2775(6)
_cell_length_c                   10.9475(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.634(4)
_cell_angle_gamma                90
_cell_volume                     589.90(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.302
_cell_measurement_theta_min      2.849
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8675.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0010
0.00 0.00 1.00 0.0390
0.00 1.00 0.00 0.0890
0.00 -1.00 0.00 0.2170
1.00 0.00 -1.00 0.0330
-1.00 0.00 1.00 0.0210
1.00 1.00 -1.00 0.0740
-1.00 1.00 0.00 0.0650
1.00 0.00 0.00 0.0400
-1.00 0.00 0.00 0.0140

_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30549
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_min         3.189
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2873
_reflns_number_total             2918
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O2-H2
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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_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 0.32901(5) 0.81642(7) 1.01547(3) 0.01520(11) Uani 1 1 d . . . . .
O1 O 0.10417(16) 0.6606(2) 0.53774(13) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.14051(17) 0.5160(2) 0.32374(13) 0.0224(3) Uani 1 1 d D . . . .
H2 H 0.112(4) 0.609(5) 0.379(3) 0.054(10) Uiso 1 1 d D . . . .
O3 O 0.23161(17) 0.9977(2) 1.03577(14) 0.0232(3) Uani 1 1 d . . . . .
O4 O 0.47282(15) 0.7921(3) 1.09666(12) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.36049(19) 0.8153(4) 0.85736(14) 0.0170(3) Uani 1 1 d . . . . .
H1A H 0.379967 0.961187 0.828297 0.020 Uiso 1 1 calc R U . . .
H1B H 0.449894 0.723332 0.843603 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2077(2) 0.7255(3) 0.79205(16) 0.0152(3) Uani 1 1 d . . . . .
H2A H 0.146866 0.833960 0.739606 0.018 Uiso 1 1 calc R U . . .
C3 C 0.1080(2) 0.6140(3) 0.88561(17) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.007802 0.688633 0.894878 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2122(2) 0.5825(3) 1.00691(18) 0.0188(4) Uani 1 1 d . . . . .
H4A H 0.276751 0.452584 1.004830 0.023 Uiso 1 1 calc R U . . .
H4B H 0.149847 0.573380 1.077134 0.023 Uiso 1 1 calc R U . . .
C5 C 0.0889(2) 0.4174(3) 0.79927(18) 0.0195(4) Uani 1 1 d . . . . .
H5A H -0.014681 0.407691 0.750500 0.023 Uiso 1 1 calc R U . . .
H5B H 0.117475 0.280808 0.841203 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2190(2) 0.5095(3) 0.72568(16) 0.0155(3) Uani 1 1 d . . . . .
H6 H 0.321466 0.438980 0.750822 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1819(2) 0.5128(3) 0.58737(16) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.23940(19) 0.3397(3) 0.51379(15) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.2172(2) 0.3523(3) 0.38371(16) 0.0165(4) Uani 1 1 d . . . . .
C10 C 0.2764(2) 0.1917(3) 0.31374(17) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.263920 0.201636 0.226566 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3528(2) 0.0191(3) 0.37044(19) 0.0207(4) Uani 1 1 d . . . . .
H11 H 0.391510 -0.089652 0.321820 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3739(2) 0.0020(3) 0.49887(18) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.425913 -0.117824 0.537459 0.023 Uiso 1 1 calc R U . . .
C13 C 0.3179(2) 0.1621(3) 0.56875(17) 0.0170(4) Uani 1 1 d . . . . .
H13 H 0.333018 0.151667 0.655880 0.020 Uiso 1 1 calc R 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 O3 1.4478(15) . ?
S1 O4 1.4500(13) . ?
S1 C1 1.7830(16) . ?
S1 C4 1.778(2) . ?
O1 C7 1.234(2) . ?
O2 H2 0.89(2) . ?
O2 C9 1.351(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.534(2) . ?
C2 H2A 1.0000 . ?
C2 C3 1.577(3) . ?
C2 C6 1.547(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.529(3) . ?
C3 C5 1.552(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.567(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.511(2) . ?
C7 C8 1.473(2) . ?
C8 C9 1.417(2) . ?
C8 C13 1.404(3) . ?
C9 C10 1.398(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?

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
O3 S1 O4 117.45(9) . . ?
O3 S1 C1 107.98(10) . . ?
O3 S1 C4 108.70(9) . . ?
O4 S1 C1 112.25(8) . . ?
O4 S1 C4 112.74(10) . . ?
C4 S1 C1 95.46(9) . . ?
C9 O2 H2 109(3) . . ?
S1 C1 H1A 111.1 . . ?
S1 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 S1 103.55(12) . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C1 C2 H2A 112.6 . . ?
C1 C2 C3 111.47(14) . . ?
C1 C2 C6 116.36(16) . . ?
C3 C2 H2A 112.6 . . ?
C6 C2 H2A 112.6 . . ?
C6 C2 C3 89.10(14) . . ?
C2 C3 H3 113.7 . . ?
C4 C3 C2 108.08(15) . . ?
C4 C3 H3 113.7 . . ?
C4 C3 C5 115.90(17) . . ?
C5 C3 C2 89.14(14) . . ?
C5 C3 H3 113.7 . . ?
S1 C4 H4A 111.3 . . ?
S1 C4 H4B 111.3 . . ?
C3 C4 S1 102.30(13) . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C3 C5 H5A 113.8 . . ?
C3 C5 H5B 113.8 . . ?
C3 C5 C6 89.29(14) . . ?
H5A C5 H5B 111.0 . . ?
C6 C5 H5A 113.8 . . ?
C6 C5 H5B 113.8 . . ?
C2 C6 C5 89.69(14) . . ?
C2 C6 H6 111.1 . . ?
C5 C6 H6 111.1 . . ?
C7 C6 C2 116.17(16) . . ?
C7 C6 C5 116.02(15) . . ?
C7 C6 H6 111.1 . . ?
O1 C7 C6 119.54(17) . . ?
O1 C7 C8 120.98(16) . . ?
C8 C7 C6 119.48(16) . . ?
C9 C8 C7 119.57(17) . . ?
C13 C8 C7 121.89(16) . . ?
C13 C8 C9 118.53(16) . . ?
O2 C9 C8 122.18(17) . . ?
O2 C9 C10 118.17(16) . . ?
C10 C9 C8 119.65(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.42(18) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.81(18) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.07(18) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.49(17) . . ?
C12 C13 H13 119.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.89(2) 1.78(3) 2.565(2) 145(4) . yes

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 C1 C2 C3 -15.7(2) . . . . ?
S1 C1 C2 C6 -115.87(15) . . . . ?
O1 C7 C8 C9 5.6(3) . . . . ?
O1 C7 C8 C13 -175.17(18) . . . . ?
O2 C9 C10 C11 -178.67(17) . . . . ?
O3 S1 C1 C2 -77.76(16) . . . . ?
O3 S1 C4 C3 69.05(14) . . . . ?
O4 S1 C1 C2 151.22(14) . . . . ?
O4 S1 C4 C3 -158.92(12) . . . . ?
C1 S1 C4 C3 -42.03(14) . . . . ?
C1 C2 C3 C4 -13.7(2) . . . . ?
C1 C2 C3 C5 -130.70(17) . . . . ?
C1 C2 C6 C5 126.10(16) . . . . ?
C1 C2 C6 C7 -114.81(18) . . . . ?
C2 C3 C4 S1 36.34(17) . . . . ?
C2 C3 C5 C6 12.44(14) . . . . ?
C2 C6 C7 O1 -20.7(2) . . . . ?
C2 C6 C7 C8 159.14(15) . . . . ?
C3 C2 C6 C5 12.48(14) . . . . ?
C3 C2 C6 C7 131.57(16) . . . . ?
C3 C5 C6 C2 -12.68(14) . . . . ?
C3 C5 C6 C7 -131.90(17) . . . . ?
C4 S1 C1 C2 33.92(16) . . . . ?
C4 C3 C5 C6 -97.30(17) . . . . ?
C5 C3 C4 S1 134.45(14) . . . . ?
C5 C6 C7 O1 82.8(2) . . . . ?
C5 C6 C7 C8 -97.4(2) . . . . ?
C6 C2 C3 C4 104.44(16) . . . . ?
C6 C2 C3 C5 -12.60(14) . . . . ?
C6 C7 C8 C9 -174.22(16) . . . . ?
C6 C7 C8 C13 5.0(3) . . . . ?
C7 C8 C9 O2 -1.9(3) . . . . ?
C7 C8 C9 C10 177.82(16) . . . . ?
C7 C8 C13 C12 -178.89(17) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C13 C8 C9 O2 178.84(16) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
