# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc2840yd
_database_code_depnum_ccdc_archive 'CCDC 2089243'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2CC01322C 2022
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.	2022-12-22 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 . . .


_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

####################################################################### 
# 
# 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_s21ab1
_database_code_depnum_ccdc_archive 'CCDC 2095960'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2022-12-22 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 H10 O2 S2'
_chemical_formula_sum            'C7 H10 O2 S2'
_chemical_formula_weight         190.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.33251(11)
_cell_length_b                   7.69444(17)
_cell_length_c                   8.95591(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.8866(17)
_cell_angle_gamma                90
_cell_volume                     433.229(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5568
_cell_measurement_theta_min      4.9630
_cell_measurement_theta_max      73.4230

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    5.163
_shelx_estimated_absorpt_T_min   0.181
_shelx_estimated_absorpt_T_max   0.608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -6 0.0517
0 0 6 0.0371
0 -5 1 0.1998
4 1 0 0.1573
-4 1 0 0.1671
0 5 -1 0.2632
1 5 -1 0.2452
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.2695 0.2113 -5.7077 -0.9809 0.1287 -0.1456
0.2515 0.2349 5.7113 0.9899 -0.1298 0.0566
0.0776 -4.9683 0.5626 0.0020 0.0351 0.9994
4.0827 0.5531 -0.4899 -0.0256 -0.9982 -0.0539
-4.0120 1.0441 0.2991 0.0244 0.9637 -0.2660
-0.2040 4.9625 -0.5487 -0.0013 -0.0043 -1.0000
1.0231 4.8171 -0.6602 -0.0088 -0.3010 -0.9536
_exptl_absorpt_correction_T_min  0.136
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.850
_oxdiff_exptl_absorpt_empirical_full_max 1.533
_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                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            6162
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.974
_diffrn_reflns_theta_max         73.426
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             1504
_reflns_number_gt                1504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_max     0.699
_reflns_Friedel_fraction_full    0.717

_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_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)+(0.0636P)²+0.0078P] 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 563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1504
_refine_ls_number_parameters     100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.35416(8) 0.52115(8) 0.33855(6) 0.02844(18) Uani 1 1 d . . . . .
S2 S 0.79903(8) 0.58381(9) 0.43746(5) 0.03059(19) Uani 1 1 d . . . . .
O1 O 1.0049(2) 0.5071(3) 0.86922(17) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.4979(2) 0.5174(3) 0.61892(16) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.5457(3) 0.5408(3) 0.4804(2) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.9645(3) 0.5934(4) 0.6167(2) 0.0294(5) Uani 1 1 d . . . . .
H2A H 1.108614 0.549737 0.604912 0.035 Uiso 1 1 calc R U . . .
H2B H 0.977692 0.715486 0.651344 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8693(3) 0.4851(3) 0.7322(2) 0.0231(5) Uani 1 1 d . . . . .
H3 H 0.864857 0.359958 0.701723 0.028 Uiso 1 1 calc R U . . .
C4 C 0.9350(4) 0.4050(4) 0.9886(3) 0.0353(6) Uani 1 1 d . . . . .
H4A H 1.037814 0.417532 1.080315 0.042 Uiso 1 1 calc R U . . .
H4B H 0.930027 0.280892 0.959359 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7166(4) 0.4625(4) 1.0220(3) 0.0345(6) Uani 1 1 d . . . . .
H5A H 0.723437 0.583794 1.059156 0.041 Uiso 1 1 calc R U . . .
H5B H 0.668672 0.387640 1.101280 0.041 Uiso 1 1 calc R U . . .
C6 C 0.5583(4) 0.4503(4) 0.8794(2) 0.0297(5) Uani 1 1 d . . . . .
H6A H 0.534051 0.326987 0.850806 0.036 Uiso 1 1 calc R U . . .
H6B H 0.420465 0.501924 0.897546 0.036 Uiso 1 1 calc R U . . .
C7 C 0.6485(3) 0.5476(3) 0.7537(2) 0.0229(5) Uani 1 1 d . . . . .
H7 H 0.653609 0.674673 0.777292 0.027 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 C1 1.655(2) . ?
S2 C1 1.726(2) . ?
S2 C2 1.810(2) . ?
O1 C3 1.421(2) . ?
O1 C4 1.438(3) . ?
O2 C1 1.324(2) . ?
O2 C7 1.464(2) . ?
C2 C3 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.513(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?

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 C2 105.34(9) . . ?
C3 O1 C4 111.61(17) . . ?
C1 O2 C7 123.46(16) . . ?
O2 C1 S1 118.56(15) . . ?
O2 C1 S2 123.92(15) . . ?
S1 C1 S2 117.49(12) . . ?
C3 C2 S2 110.44(16) . . ?
C3 C2 H2A 109.6 . . ?
S2 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
S2 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C2 106.04(17) . . ?
O1 C3 C7 108.93(17) . . ?
C2 C3 C7 111.27(19) . . ?
O1 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C7 C3 H3 110.2 . . ?
O1 C4 C5 110.9(2) . . ?
O1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 109.86(18) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 108.76(19) . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O2 C7 C3 111.40(16) . . ?
O2 C7 C6 105.50(18) . . ?
C3 C7 C6 111.89(19) . . ?
O2 C7 H7 109.3 . . ?
C3 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?

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
C7 O2 C1 S1 -173.91(18) . . . . ?
C7 O2 C1 S2 8.3(4) . . . . ?
C2 S2 C1 O2 -1.4(3) . . . . ?
C2 S2 C1 S1 -179.21(15) . . . . ?
C1 S2 C2 C3 26.4(2) . . . . ?
C4 O1 C3 C2 -178.1(2) . . . . ?
C4 O1 C3 C7 62.0(3) . . . . ?
S2 C2 C3 O1 -177.55(17) . . . . ?
S2 C2 C3 C7 -59.2(2) . . . . ?
C3 O1 C4 C5 -62.7(3) . . . . ?
O1 C4 C5 C6 57.0(3) . . . . ?
C4 C5 C6 C7 -52.3(3) . . . . ?
C1 O2 C7 C3 -39.9(3) . . . . ?
C1 O2 C7 C6 -161.5(2) . . . . ?
O1 C3 C7 O2 -176.23(19) . . . . ?
C2 C3 C7 O2 67.2(3) . . . . ?
O1 C3 C7 C6 -58.4(3) . . . . ?
C2 C3 C7 C6 -174.94(19) . . . . ?
C5 C6 C7 O2 175.22(19) . . . . ?
C5 C6 C7 C3 53.9(3) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_e22ab1
_database_code_depnum_ccdc_archive 'CCDC 2177255'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-12-22 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 H10 O3 S'
_chemical_formula_sum            'C7 H10 O3 S'
_chemical_formula_weight         174.21

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                   6.0382(2)
_cell_length_b                   6.9857(2)
_cell_length_c                   18.8158(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     793.67(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9215
_cell_measurement_theta_min      3.5370
_cell_measurement_theta_max      30.1630

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.696
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.448
_exptl_absorpt_coefficient_mu    0.361
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_T_min  0.92518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.917
_oxdiff_exptl_absorpt_empirical_full_max 1.095
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(6)
_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            13165
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_max         30.232
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2192
_reflns_number_gt                2152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_max     0.894
_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 1.171.41.118a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_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)+(0.0367P)²+0.1501P] 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 831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2192
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_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
S S 0.65664(6) 0.00041(6) 0.28448(2) 0.02351(11) Uani 1 1 d . . . . .
O1 O 0.3244(2) -0.05162(19) 0.36670(7) 0.0349(3) Uani 1 1 d . . . . .
O2 O 0.51852(19) 0.19783(18) 0.40104(6) 0.0249(3) Uani 1 1 d . . . . .
O3 O 1.04326(19) 0.42816(17) 0.34852(6) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.4801(3) 0.0531(2) 0.35638(8) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.6717(2) 0.3517(2) 0.38445(7) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.605140 0.437349 0.347609 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7016(3) 0.4620(2) 0.45332(8) 0.0234(3) Uani 1 1 d . . . . .
H3A H 0.749585 0.373840 0.491525 0.028 Uiso 1 1 calc R U . . .
H3B H 0.559119 0.520507 0.467658 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8753(3) 0.6179(2) 0.44262(9) 0.0281(4) Uani 1 1 d . . . . .
H4A H 0.818758 0.715475 0.409048 0.034 Uiso 1 1 calc R U . . .
H4B H 0.906794 0.681729 0.488509 0.034 Uiso 1 1 calc R U . . .
C5 C 1.0862(3) 0.5294(2) 0.41338(8) 0.0249(3) Uani 1 1 d . . . . .
H5A H 1.196660 0.631371 0.404498 0.030 Uiso 1 1 calc R U . . .
H5B H 1.148972 0.440064 0.448913 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8921(2) 0.27425(19) 0.35778(7) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.953258 0.179001 0.392257 0.019 Uiso 1 1 calc R U . . .
C7 C 0.8682(3) 0.1843(2) 0.28506(8) 0.0230(3) Uani 1 1 d . . . . .
H7A H 1.011542 0.127505 0.270655 0.028 Uiso 1 1 calc R U . . .
H7B H 0.829349 0.284580 0.250038 0.028 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
S C1 1.7610(16) . ?
S C7 1.8116(16) . ?
O1 C1 1.2070(19) . ?
O2 C1 1.3351(18) . ?
O2 C2 1.4522(18) . ?
O3 C6 1.4211(16) . ?
O3 C5 1.4342(18) . ?
C2 C3 1.5184(19) . ?
C2 C6 1.5216(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.526(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5125(19) . ?
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 S C7 105.90(7) . . ?
C1 O2 C2 122.40(11) . . ?
C6 O3 C5 112.64(11) . . ?
O1 C1 O2 119.53(14) . . ?
O1 C1 S 117.93(12) . . ?
O2 C1 S 122.46(11) . . ?
O2 C2 C3 105.53(11) . . ?
O2 C2 C6 111.39(11) . . ?
C3 C2 C6 110.98(12) . . ?
O2 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C6 C2 H2 109.6 . . ?
C2 C3 C4 109.36(13) . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C3 109.48(12) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
O3 C5 C4 110.95(12) . . ?
O3 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
O3 C6 C7 105.35(11) . . ?
O3 C6 C2 109.45(11) . . ?
C7 C6 C2 111.26(11) . . ?
O3 C6 H6 110.2 . . ?
C7 C6 H6 110.2 . . ?
C2 C6 H6 110.2 . . ?
C6 C7 S 111.55(10) . . ?
C6 C7 H7A 109.3 . . ?
S C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
S C7 H7B 109.3 . . ?
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 O2 C1 O1 -166.84(14) . . . . ?
C2 O2 C1 S 16.3(2) . . . . ?
C7 S C1 O1 179.99(13) . . . . ?
C7 S C1 O2 -3.12(16) . . . . ?
C1 O2 C2 C3 -169.06(14) . . . . ?
C1 O2 C2 C6 -48.53(18) . . . . ?
O2 C2 C3 C4 175.46(12) . . . . ?
C6 C2 C3 C4 54.66(16) . . . . ?
C2 C3 C4 C5 -53.68(17) . . . . ?
C6 O3 C5 C4 -61.41(16) . . . . ?
C3 C4 C5 O3 56.69(17) . . . . ?
C5 O3 C6 C7 -179.59(12) . . . . ?
C5 O3 C6 C2 60.68(15) . . . . ?
O2 C2 C6 O3 -174.63(11) . . . . ?
C3 C2 C6 O3 -57.36(15) . . . . ?
O2 C2 C6 C7 69.35(15) . . . . ?
C3 C2 C6 C7 -173.38(12) . . . . ?
O3 C6 C7 S -173.64(10) . . . . ?
C2 C6 C7 S -55.12(15) . . . . ?
C1 S C7 C6 22.81(13) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: layering CHCl3 with n-hexane'
####################################################################### 
# 
# 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_e22ab3
_database_code_depnum_ccdc_archive 'CCDC 2177256'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-12-22 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 H10 O3 S'
_chemical_formula_sum            'C7 H10 O3 S'
_chemical_formula_weight         174.21

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           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'

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

_cell_length_a                   12.5990(3)
_cell_length_b                   6.90114(15)
_cell_length_c                   18.8705(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.949(3)
_cell_angle_gamma                90
_cell_volume                     1599.02(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8370
_cell_measurement_theta_min      3.8290
_cell_measurement_theta_max      27.4400

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.358
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_T_min  0.94340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.915
_oxdiff_exptl_absorpt_empirical_full_max 1.097
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.9(6)
_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            12814
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.153
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3659
_reflns_number_gt                3565
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.999
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_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)+(0.0315P)²+0.3966P] 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 1555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3659
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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 0.68972(4) 1.09214(7) 0.68856(3) 0.02727(13) Uani 1 1 d . . . . .
O1 O 0.65144(11) 0.8362(2) 0.58660(8) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.79766(11) 0.4116(2) 0.54205(7) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.82550(11) 0.8435(2) 0.65781(7) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.72475(15) 0.9119(3) 0.64115(10) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.67135(17) 0.6642(3) 0.54626(11) 0.0246(4) Uani 1 1 d . . . . .
H2A H 0.685133 0.703497 0.498669 0.029 Uiso 1 1 calc R U . . .
H2B H 0.606129 0.579848 0.537143 0.029 Uiso 1 1 calc R U . . .
C3 C 0.76792(15) 0.5537(3) 0.58860(10) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.749486 0.490545 0.632007 0.022 Uiso 1 1 calc R U . . .
C4 C 0.89197(17) 0.3035(3) 0.57968(11) 0.0259(4) Uani 1 1 d . . . . .
H4A H 0.910932 0.205142 0.546368 0.031 Uiso 1 1 calc R U . . .
H4B H 0.874099 0.234662 0.621542 0.031 Uiso 1 1 calc R U . . .
C5 C 0.98911(16) 0.4345(3) 0.60657(11) 0.0239(4) Uani 1 1 d . . . . .
H5A H 1.011970 0.493366 0.564519 0.029 Uiso 1 1 calc R U . . .
H5B H 1.050756 0.357191 0.634336 0.029 Uiso 1 1 calc R U . . .
C6 C 0.96036(15) 0.5951(3) 0.65533(10) 0.0207(4) Uani 1 1 d . . . . .
H6A H 0.945431 0.538895 0.700380 0.025 Uiso 1 1 calc R U . . .
H6B H 1.021415 0.687998 0.668838 0.025 Uiso 1 1 calc R U . . .
C7 C 0.86028(15) 0.6958(3) 0.61212(10) 0.0174(4) Uani 1 1 d . . . . .
H7 H 0.877639 0.758529 0.568309 0.021 Uiso 1 1 calc R U . . .
S2 S 0.86521(5) -0.09205(8) 0.41799(3) 0.03132(14) Uani 1 1 d . . . . .
O4 O 0.68987(13) 0.0531(2) 0.44385(8) 0.0305(4) Uani 1 1 d . . . . .
O5 O 0.51422(12) 0.4640(2) 0.37549(9) 0.0320(4) Uani 1 1 d . . . . .
O6 O 0.76271(11) 0.2122(2) 0.35932(8) 0.0242(3) Uani 1 1 d . . . . .
C8 C 0.76631(16) 0.0694(3) 0.40653(10) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.59467(17) 0.1809(3) 0.43542(12) 0.0280(5) Uani 1 1 d . . . . .
H9A H 0.602603 0.264555 0.478915 0.034 Uiso 1 1 calc R U . . .
H9B H 0.528221 0.101445 0.431648 0.034 Uiso 1 1 calc R U . . .
C10 C 0.58267(16) 0.3054(3) 0.36897(11) 0.0238(4) Uani 1 1 d . . . . .
H10 H 0.550009 0.228130 0.324597 0.029 Uiso 1 1 calc R U . . .
C11 C 0.49689(19) 0.5821(4) 0.31070(13) 0.0383(6) Uani 1 1 d . . . . .
H11A H 0.446586 0.689525 0.314893 0.046 Uiso 1 1 calc R U . . .
H11B H 0.462659 0.502726 0.267978 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6039(2) 0.6649(4) 0.29951(13) 0.0345(5) Uani 1 1 d . . . . .
H12A H 0.634099 0.755502 0.339647 0.041 Uiso 1 1 calc R U . . .
H12B H 0.590326 0.738759 0.253370 0.041 Uiso 1 1 calc R U . . .
C13 C 0.68687(18) 0.5041(3) 0.29715(11) 0.0274(5) Uani 1 1 d . . . . .
H13A H 0.663217 0.425088 0.252615 0.033 Uiso 1 1 calc R U . . .
H13B H 0.758988 0.560859 0.297013 0.033 Uiso 1 1 calc R U . . .
C14 C 0.69368(15) 0.3802(3) 0.36380(10) 0.0201(4) Uani 1 1 d . . . . .
H14 H 0.725942 0.457303 0.408286 0.024 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 C1 1.649(2) . ?
O1 C1 1.327(2) . ?
O1 C2 1.462(3) . ?
O2 C3 1.422(2) . ?
O2 C4 1.447(2) . ?
O3 C1 1.324(2) . ?
O3 C7 1.464(2) . ?
C2 C3 1.505(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.510(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.515(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.535(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.509(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
S2 C8 1.649(2) . ?
O4 C8 1.319(2) . ?
O4 C9 1.468(3) . ?
O5 C10 1.416(2) . ?
O5 C11 1.445(3) . ?
O6 C8 1.322(2) . ?
O6 C14 1.463(2) . ?
C9 C10 1.499(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.514(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.522(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.532(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.507(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?

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 C2 123.57(15) . . ?
C3 O2 C4 110.70(14) . . ?
C1 O3 C7 120.38(14) . . ?
O3 C1 O1 120.50(17) . . ?
O3 C1 S1 119.93(14) . . ?
O1 C1 S1 119.57(14) . . ?
O1 C2 C3 110.34(16) . . ?
O1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C2 108.37(15) . . ?
O2 C3 C7 109.70(15) . . ?
C2 C3 C7 107.76(16) . . ?
O2 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
C7 C3 H3 110.3 . . ?
O2 C4 C5 111.69(17) . . ?
O2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 110.51(16) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 106.83(15) . . ?
C7 C6 H6A 110.4 . . ?
C5 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O3 C7 C6 109.06(15) . . ?
O3 C7 C3 108.21(14) . . ?
C6 C7 C3 110.81(16) . . ?
O3 C7 H7 109.6 . . ?
C6 C7 H7 109.6 . . ?
C3 C7 H7 109.6 . . ?
C8 O4 C9 124.55(17) . . ?
C10 O5 C11 110.00(16) . . ?
C8 O6 C14 118.86(14) . . ?
O4 C8 O6 120.29(18) . . ?
O4 C8 S2 119.52(16) . . ?
O6 C8 S2 120.18(14) . . ?
O4 C9 C10 111.20(16) . . ?
O4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O5 C10 C9 108.63(16) . . ?
O5 C10 C14 109.33(17) . . ?
C9 C10 C14 109.13(16) . . ?
O5 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
C14 C10 H10 109.9 . . ?
O5 C11 C12 111.02(17) . . ?
O5 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
O5 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.3(2) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 107.35(17) . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O6 C14 C13 108.94(15) . . ?
O6 C14 C10 107.64(15) . . ?
C13 C14 C10 111.50(16) . . ?
O6 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C10 C14 H14 109.6 . . ?

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
C7 O3 C1 O1 5.7(3) . . . . ?
C7 O3 C1 S1 -174.40(13) . . . . ?
C2 O1 C1 O3 6.3(3) . . . . ?
C2 O1 C1 S1 -173.58(15) . . . . ?
C1 O1 C2 C3 17.7(3) . . . . ?
C4 O2 C3 C2 178.74(17) . . . . ?
C4 O2 C3 C7 61.3(2) . . . . ?
O1 C2 C3 O2 -168.51(15) . . . . ?
O1 C2 C3 C7 -49.9(2) . . . . ?
C3 O2 C4 C5 -59.3(2) . . . . ?
O2 C4 C5 C6 56.1(2) . . . . ?
C4 C5 C6 C7 -54.4(2) . . . . ?
C1 O3 C7 C6 -160.29(16) . . . . ?
C1 O3 C7 C3 -39.7(2) . . . . ?
C5 C6 C7 O3 176.73(15) . . . . ?
C5 C6 C7 C3 57.71(19) . . . . ?
O2 C3 C7 O3 178.06(14) . . . . ?
C2 C3 C7 O3 60.28(19) . . . . ?
O2 C3 C7 C6 -62.41(19) . . . . ?
C2 C3 C7 C6 179.81(16) . . . . ?
C9 O4 C8 O6 2.4(3) . . . . ?
C9 O4 C8 S2 -176.40(15) . . . . ?
C14 O6 C8 O4 17.5(3) . . . . ?
C14 O6 C8 S2 -163.67(14) . . . . ?
C8 O4 C9 C10 11.8(3) . . . . ?
C11 O5 C10 C9 -177.35(17) . . . . ?
C11 O5 C10 C14 63.7(2) . . . . ?
O4 C9 C10 O5 -161.54(16) . . . . ?
O4 C9 C10 C14 -42.4(2) . . . . ?
C10 O5 C11 C12 -61.4(2) . . . . ?
O5 C11 C12 C13 55.8(3) . . . . ?
C11 C12 C13 C14 -51.7(2) . . . . ?
C8 O6 C14 C13 -169.73(17) . . . . ?
C8 O6 C14 C10 -48.7(2) . . . . ?
C12 C13 C14 O6 173.60(16) . . . . ?
C12 C13 C14 C10 54.9(2) . . . . ?
O5 C10 C14 O6 178.36(15) . . . . ?
C9 C10 C14 O6 59.67(19) . . . . ?
O5 C10 C14 C13 -62.2(2) . . . . ?
C9 C10 C14 C13 179.10(17) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: layering CHCl3 with n-hexane'
####################################################################### 
# 
# 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_s22ab1
_database_code_depnum_ccdc_archive 'CCDC 2177257'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-12-22 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 H10 O4'
_chemical_formula_sum            'C7 H10 O4'
_chemical_formula_weight         158.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   8.79278(12)
_cell_length_b                   6.11294(9)
_cell_length_c                   13.39685(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.4175(12)
_cell_angle_gamma                90
_cell_volume                     720.058(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8353
_cell_measurement_theta_min      5.0270
_cell_measurement_theta_max      72.7690

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.029
_shelx_estimated_absorpt_T_min   0.734
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_T_min  0.67311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.648
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_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                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            11144
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.030
_diffrn_reflns_theta_max         72.888
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2780
_reflns_number_gt                2734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.941

_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_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)+(0.0394P)²+0.0781P] 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 1160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2780
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
O1 O 0.45713(14) 0.6902(2) 0.21514(9) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.39630(15) 0.3494(2) 0.18225(10) 0.0312(3) Uani 1 1 d . . . . .
O3 O 0.20738(14) 0.11697(19) -0.03635(9) 0.0258(3) Uani 1 1 d . . . . .
O4 O 0.31359(13) 0.63425(19) 0.08210(8) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.39032(17) 0.5627(3) 0.16214(12) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.3276(2) 0.1814(3) 0.11935(13) 0.0286(4) Uani 1 1 d . . . . .
H2A H 0.230747 0.132168 0.149082 0.034 Uiso 1 1 calc R U . . .
H2B H 0.396593 0.053738 0.115321 0.034 Uiso 1 1 calc R U . . .
C3 C 0.29815(18) 0.2700(3) 0.01635(12) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.396432 0.293803 -0.019145 0.026 Uiso 1 1 calc R U . . .
C4 C 0.17155(19) 0.1962(3) -0.13534(12) 0.0251(4) Uani 1 1 d . . . . .
H4A H 0.109888 0.085374 -0.171245 0.030 Uiso 1 1 calc R U . . .
H4B H 0.266915 0.218151 -0.172867 0.030 Uiso 1 1 calc R U . . .
C5 C 0.08447(18) 0.4096(3) -0.13123(11) 0.0230(3) Uani 1 1 d . . . . .
H5A H -0.015159 0.384864 -0.099174 0.028 Uiso 1 1 calc R U . . .
H5B H 0.065471 0.463230 -0.199923 0.028 Uiso 1 1 calc R U . . .
C6 C 0.17375(19) 0.5824(3) -0.07226(12) 0.0230(3) Uani 1 1 d . . . . .
H6A H 0.267170 0.623373 -0.108583 0.028 Uiso 1 1 calc R U . . .
H6B H 0.111035 0.715352 -0.063279 0.028 Uiso 1 1 calc R U . . .
C7 C 0.21439(17) 0.4849(3) 0.02783(11) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.119467 0.460426 0.066947 0.023 Uiso 1 1 calc R U . . .
O5 O 0.05683(15) 0.3263(2) 0.28091(10) 0.0362(3) Uani 1 1 d . . . . .
O6 O 0.12837(14) 0.6633(2) 0.31174(9) 0.0314(3) Uani 1 1 d . . . . .
O7 O 0.33197(14) 0.8846(2) 0.52708(8) 0.0269(3) Uani 1 1 d . . . . .
O8 O 0.14121(14) 0.3944(2) 0.43264(9) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.10675(18) 0.4563(3) 0.33956(12) 0.0253(4) Uani 1 1 d . . . . .
C9 C 0.2038(2) 0.8278(3) 0.37337(12) 0.0259(4) Uani 1 1 d . . . . .
H9A H 0.127046 0.929772 0.400625 0.031 Uiso 1 1 calc R U . . .
H9B H 0.275201 0.913345 0.332006 0.031 Uiso 1 1 calc R U . . .
C10 C 0.28936(17) 0.7207(3) 0.45787(11) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.381778 0.644794 0.431963 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4141(2) 0.7900(3) 0.60996(12) 0.0300(4) Uani 1 1 d . . . . .
H11A H 0.444475 0.907490 0.656902 0.036 Uiso 1 1 calc R U . . .
H11B H 0.507854 0.719467 0.585139 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3193(2) 0.6220(3) 0.66487(12) 0.0278(4) Uani 1 1 d . . . . .
H12A H 0.231483 0.695332 0.696352 0.033 Uiso 1 1 calc R U . . .
H12B H 0.381495 0.554022 0.718400 0.033 Uiso 1 1 calc R U . . .
C13 C 0.26193(19) 0.4443(3) 0.59333(12) 0.0260(4) Uani 1 1 d . . . . .
H13A H 0.348132 0.354945 0.569282 0.031 Uiso 1 1 calc R U . . .
H13B H 0.189396 0.346765 0.627836 0.031 Uiso 1 1 calc R U . . .
C14 C 0.18436(17) 0.5572(3) 0.50678(11) 0.0218(3) Uani 1 1 d . . . . .
H14 H 0.091269 0.634174 0.530946 0.026 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
O1 C1 1.204(2) . ?
O2 C1 1.333(2) . ?
O2 C2 1.456(2) . ?
O3 C3 1.4152(19) . ?
O3 C4 1.4444(19) . ?
O4 C1 1.3363(19) . ?
O4 C7 1.4539(18) . ?
C2 C3 1.503(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.514(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.532(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.508(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
O5 C8 1.199(2) . ?
O6 C8 1.333(2) . ?
O6 C9 1.458(2) . ?
O7 C10 1.4140(19) . ?
O7 C11 1.441(2) . ?
O8 C8 1.336(2) . ?
O8 C14 1.454(2) . ?
C9 C10 1.505(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.513(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.516(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.532(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.508(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14 1.0000 . ?

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 O2 C2 123.87(14) . . ?
C3 O3 C4 110.79(12) . . ?
C1 O4 C7 119.57(12) . . ?
O1 C1 O2 119.72(15) . . ?
O1 C1 O4 120.18(16) . . ?
O2 C1 O4 120.08(15) . . ?
O2 C2 C3 110.19(14) . . ?
O2 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
O2 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O3 C3 C2 108.21(13) . . ?
O3 C3 C7 110.56(12) . . ?
C2 C3 C7 107.47(14) . . ?
O3 C3 H3 110.2 . . ?
C2 C3 H3 110.2 . . ?
C7 C3 H3 110.2 . . ?
O3 C4 C5 111.25(13) . . ?
O3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.83(13) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 107.65(13) . . ?
C7 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O4 C7 C6 109.51(12) . . ?
O4 C7 C3 107.76(12) . . ?
C6 C7 C3 111.40(13) . . ?
O4 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
C3 C7 H7 109.4 . . ?
C8 O6 C9 124.18(13) . . ?
C10 O7 C11 110.48(13) . . ?
C8 O8 C14 120.00(14) . . ?
O5 C8 O6 119.89(16) . . ?
O5 C8 O8 120.25(18) . . ?
O6 C8 O8 119.86(15) . . ?
O6 C9 C10 110.40(13) . . ?
O6 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
O6 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O7 C10 C9 108.27(13) . . ?
O7 C10 C14 110.10(12) . . ?
C9 C10 C14 108.05(13) . . ?
O7 C10 H10 110.1 . . ?
C9 C10 H10 110.1 . . ?
C14 C10 H10 110.1 . . ?
O7 C11 C12 111.80(14) . . ?
O7 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O7 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 110.89(13) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 107.55(14) . . ?
C14 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O8 C14 C13 109.03(13) . . ?
O8 C14 C10 108.25(12) . . ?
C13 C14 C10 111.18(13) . . ?
O8 C14 H14 109.5 . . ?
C13 C14 H14 109.5 . . ?
C10 C14 H14 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
C2 O2 C1 O1 -175.97(16) . . . . ?
C2 O2 C1 O4 2.4(3) . . . . ?
C7 O4 C1 O1 -170.41(13) . . . . ?
C7 O4 C1 O2 11.2(2) . . . . ?
C1 O2 C2 C3 19.0(2) . . . . ?
C4 O3 C3 C2 178.39(13) . . . . ?
C4 O3 C3 C7 60.94(17) . . . . ?
O2 C2 C3 O3 -169.55(13) . . . . ?
O2 C2 C3 C7 -50.13(18) . . . . ?
C3 O3 C4 C5 -60.20(17) . . . . ?
O3 C4 C5 C6 56.66(18) . . . . ?
C4 C5 C6 C7 -53.27(17) . . . . ?
C1 O4 C7 C6 -165.32(13) . . . . ?
C1 O4 C7 C3 -44.00(17) . . . . ?
C5 C6 C7 O4 173.75(12) . . . . ?
C5 C6 C7 C3 54.66(17) . . . . ?
O3 C3 C7 O4 -179.86(11) . . . . ?
C2 C3 C7 O4 62.24(16) . . . . ?
O3 C3 C7 C6 -59.72(17) . . . . ?
C2 C3 C7 C6 -177.62(13) . . . . ?
C9 O6 C8 O5 -172.89(15) . . . . ?
C9 O6 C8 O8 6.9(2) . . . . ?
C14 O8 C8 O5 -172.64(15) . . . . ?
C14 O8 C8 O6 7.5(2) . . . . ?
C8 O6 C9 C10 15.3(2) . . . . ?
C11 O7 C10 C9 179.78(13) . . . . ?
C11 O7 C10 C14 61.86(16) . . . . ?
O6 C9 C10 O7 -167.35(12) . . . . ?
O6 C9 C10 C14 -48.13(17) . . . . ?
C10 O7 C11 C12 -59.94(18) . . . . ?
O7 C11 C12 C13 55.5(2) . . . . ?
C11 C12 C13 C14 -52.41(18) . . . . ?
C8 O8 C14 C13 -162.90(14) . . . . ?
C8 O8 C14 C10 -41.83(18) . . . . ?
C12 C13 C14 O8 174.60(12) . . . . ?
C12 C13 C14 C10 55.34(17) . . . . ?
O7 C10 C14 O8 178.94(12) . . . . ?
C9 C10 C14 O8 60.89(16) . . . . ?
O7 C10 C14 C13 -61.33(17) . . . . ?
C9 C10 C14 C13 -179.38(14) . . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: layering CHCl3 with n-hexane'
