# Electronic Supplementary Material (ESI) for ChemComm.
# 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_e20ab1
_database_code_depnum_ccdc_archive 'CCDC 2089243'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2021-06-10 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O2 S2'
_chemical_formula_sum            'C7 H8 O2 S2'
_chemical_formula_weight         188.25

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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2400(3)
_cell_length_b                   7.3164(4)
_cell_length_c                   17.7083(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     808.46(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3575
_cell_measurement_theta_min      4.2770
_cell_measurement_theta_max      29.8990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.601
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_T_min  0.90790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.901
_oxdiff_exptl_absorpt_empirical_full_max 1.125
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            7475
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.462
_diffrn_reflns_theta_max         30.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2183
_reflns_number_gt                1985
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_max     0.848
_reflns_Friedel_fraction_full    1.000

_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2183
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0673
_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 0.34062(8) 0.50836(9) 0.20589(3) 0.02220(14) Uani 1 1 d . . . . .
S2 S 0.78444(8) 0.49895(10) 0.25384(3) 0.02125(14) Uani 1 1 d . . . . .
O1 O 0.4433(2) 0.5411(2) 0.34594(8) 0.0200(4) Uani 1 1 d . . . . .
O2 O 0.8920(2) 0.4622(2) 0.47551(8) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.5148(3) 0.5197(3) 0.27554(11) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.5925(4) 0.5827(3) 0.40690(12) 0.0168(5) Uani 1 1 d . . . . .
H2 H 0.653275 0.708041 0.399816 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4669(4) 0.5748(3) 0.47880(13) 0.0223(5) Uani 1 1 d . . . . .
H3 H 0.327342 0.626449 0.480766 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5486(3) 0.4967(4) 0.53953(11) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.464668 0.492497 0.584263 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7682(4) 0.4145(4) 0.54066(14) 0.0251(5) Uani 1 1 d . . . . .
H5A H 0.844495 0.456467 0.586519 0.030 Uiso 1 1 calc R U . . .
H5B H 0.755422 0.279844 0.543469 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7722(4) 0.4423(3) 0.40751(12) 0.0179(5) Uani 1 1 d . . . . .
H6 H 0.711510 0.316106 0.404088 0.021 Uiso 1 1 calc R U . . .
C7 C 0.9258(3) 0.4756(4) 0.34317(12) 0.0264(6) Uani 1 1 d . . . . .
H7A H 1.028005 0.372442 0.339808 0.032 Uiso 1 1 calc R U . . .
H7B H 1.008840 0.588340 0.353199 0.032 Uiso 1 1 calc R U . . .

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 0.0200(2) 0.0316(3) 0.0150(3) -0.0004(3) -0.0031(2) -0.0001(3)
S2 0.0162(2) 0.0336(3) 0.0139(2) 0.0027(3) 0.00337(19) 0.0020(3)
O1 0.0141(7) 0.0339(10) 0.0122(7) -0.0016(7) 0.0001(6) -0.0003(7)
O2 0.0172(7) 0.0396(10) 0.0142(8) 0.0010(7) -0.0029(6) -0.0022(7)
C1 0.0159(9) 0.0173(10) 0.0141(9) -0.0005(9) 0.0014(7) -0.0014(11)
C2 0.0156(10) 0.0216(10) 0.0133(11) -0.0013(8) -0.0025(9) -0.0011(9)
C3 0.0203(11) 0.0276(12) 0.0189(12) -0.0060(9) 0.0019(10) 0.0047(10)
C4 0.0234(10) 0.0322(12) 0.0149(10) -0.0029(13) 0.0040(9) 0.0027(14)
C5 0.0228(11) 0.0377(14) 0.0149(12) 0.0029(10) 0.0003(11) 0.0022(11)
C6 0.0146(9) 0.0262(11) 0.0128(11) -0.0015(9) -0.0010(9) -0.0003(9)
C7 0.0137(9) 0.0490(17) 0.0164(10) 0.0027(12) 0.0008(9) 0.0025(12)

_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 1.646(2) . ?
S2 C1 1.733(2) . ?
S2 C7 1.819(2) . ?
O1 C1 1.333(2) . ?
O1 C2 1.458(3) . ?
O2 C6 1.425(3) . ?
O2 C5 1.431(3) . ?
C2 C3 1.496(3) . ?
C2 C6 1.521(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.320(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.497(3) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.509(3) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 S2 C7 106.63(10) . . ?
C1 O1 C2 120.23(16) . . ?
C6 O2 C5 111.93(16) . . ?
O1 C1 S1 119.06(15) . . ?
O1 C1 S2 122.85(15) . . ?
S1 C1 S2 118.08(12) . . ?
O1 C2 C3 106.71(17) . . ?
O1 C2 C6 109.57(17) . . ?
C3 C2 C6 110.74(18) . . ?
O1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C6 C2 H2 109.9 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 122.6(2) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
O2 C5 C4 112.68(19) . . ?
O2 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
O2 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O2 C6 C7 106.77(17) . . ?
O2 C6 C2 108.90(17) . . ?
C7 C6 C2 110.73(19) . . ?
O2 C6 H6 110.1 . . ?
C7 C6 H6 110.1 . . ?
C2 C6 H6 110.1 . . ?
C6 C7 S2 111.33(15) . . ?
C6 C7 H7A 109.4 . . ?
S2 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
S2 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?

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
C2 O1 C1 S1 -169.50(15) . . . . ?
C2 O1 C1 S2 11.7(3) . . . . ?
C7 S2 C1 O1 8.9(3) . . . . ?
C7 S2 C1 S1 -169.88(15) . . . . ?
C1 O1 C2 C3 -173.13(19) . . . . ?
C1 O1 C2 C6 -53.2(3) . . . . ?
O1 C2 C3 C4 138.0(2) . . . . ?
C6 C2 C3 C4 18.8(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C6 O2 C5 C4 -46.0(3) . . . . ?
C3 C4 C5 O2 11.8(3) . . . . ?
C5 O2 C6 C7 -173.8(2) . . . . ?
C5 O2 C6 C2 66.6(2) . . . . ?
O1 C2 C6 O2 -168.58(16) . . . . ?
C3 C2 C6 O2 -51.1(2) . . . . ?
O1 C2 C6 C7 74.3(2) . . . . ?
C3 C2 C6 C7 -168.24(19) . . . . ?
O2 C6 C7 S2 -168.77(16) . . . . ?
C2 C6 C7 S2 -50.4(3) . . . . ?
C1 S2 C7 C6 11.5(2) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.061

_shelx_res_file                  
;
TITL shelxt_a.res in P2(1)2(1)2(1)
    e20ab1.res
    created by SHELXL-2018/3 at 11:36:14 on 14-Feb-2020
CELL  0.71073   6.2400   7.3164  17.7083   90.000   90.000   90.000
ZERR     4.00   0.0003   0.0004   0.0008    0.000    0.000    0.000
LATT  -1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SYMM  1/2 + X, 1/2 - Y, - Z
SFAC  C    H    O    S
UNIT 28 32 8 8
ACTA
FMAP   2
PLAN   5
BOND $H
CONF
TEMP -123
SIZE 0.101 0.327 0.429
LIST  4
L.S.  10
WGHT    0.031600    0.065400
FVAR       4.28473
S1    4    0.340617    0.508359    0.205893    11.00000    0.02001    0.03160 =
         0.01501   -0.00040   -0.00314   -0.00011
S2    4    0.784440    0.498954    0.253837    11.00000    0.01617    0.03363 =
         0.01394    0.00268    0.00337    0.00199
O1    3    0.443335    0.541090    0.345941    11.00000    0.01408    0.03388 =
         0.01218   -0.00161    0.00005   -0.00030
O2    3    0.891998    0.462165    0.475508    11.00000    0.01716    0.03956 =
         0.01417    0.00100   -0.00290   -0.00218
C1    1    0.514791    0.519703    0.275540    11.00000    0.01590    0.01734 =
         0.01412   -0.00048    0.00140   -0.00144
C2    1    0.592532    0.582729    0.406904    11.00000    0.01561    0.02156 =
         0.01331   -0.00129   -0.00250   -0.00105
AFIX  13
H2    2    0.653275    0.708041    0.399816    11.00000   -1.20000
AFIX   0
C3    1    0.466933    0.574841    0.478802    11.00000    0.02035    0.02756 =
         0.01885   -0.00599    0.00193    0.00473
AFIX  43
H3    2    0.327342    0.626449    0.480766    11.00000   -1.20000
AFIX   0
C4    1    0.548581    0.496721    0.539535    11.00000    0.02343    0.03216 =
         0.01491   -0.00290    0.00400    0.00271
AFIX  43
H4    2    0.464668    0.492497    0.584263    11.00000   -1.20000
AFIX   0
C5    1    0.768245    0.414541    0.540655    11.00000    0.02276    0.03774 =
         0.01490    0.00289    0.00026    0.00219
AFIX  23
H5A   2    0.844495    0.456467    0.586519    11.00000   -1.20000
H5B   2    0.755422    0.279844    0.543469    11.00000   -1.20000
AFIX   0
C6    1    0.772223    0.442326    0.407509    11.00000    0.01464    0.02622 =
         0.01285   -0.00151   -0.00097   -0.00032
AFIX  13
H6    2    0.711510    0.316106    0.404088    11.00000   -1.20000
AFIX   0
C7    1    0.925808    0.475621    0.343173    11.00000    0.01369    0.04904 =
         0.01643    0.00270    0.00083    0.00247
AFIX  23
H7A   2    1.028005    0.372442    0.339808    11.00000   -1.20000
H7B   2    1.008840    0.588340    0.353199    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0692, GooF = S = 1.094, Restrained GooF = 1.094 for all data
REM R1 = 0.0328 for 1985 Fo > 4sig(Fo) and 0.0382 for all 2183 data
REM 100 parameters refined using 0 restraints

END

WGHT      0.0316      0.0654

REM Highest difference peak  0.388,  deepest hole -0.337,  1-sigma level  0.061
Q1    1   0.6670  0.4972  0.4079  11.00000  0.05    0.39
Q2    1   0.4191  0.5597  0.2466  11.00000  0.05    0.27
Q3    1   0.8367  0.4627  0.2965  11.00000  0.05    0.24
Q4    1   0.3496  0.4264  0.1672  11.00000  0.05    0.22
Q5    1   0.3833  0.4653  0.2581  11.00000  0.05    0.21
;
_shelx_res_checksum              6752
