# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exter168
_database_code_depnum_ccdc_archive 'CCDC 2241454'
loop_
_audit_author_name
_audit_author_address
'Tamilselvi A'
;Thiagarajar College, Madurai
India
;
_audit_update_record             
;
2023-02-13 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2023-01-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O6 S'
_chemical_formula_sum            'C17 H16 O6 S'
_chemical_formula_weight         348.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7764(2)
_cell_length_b                   24.8373(6)
_cell_length_c                   9.1903(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.534(3)
_cell_angle_gamma                90
_cell_volume                     1627.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    296.9
_cell_measurement_theta_max      26.3380
_cell_measurement_theta_min      2.5440
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19686
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.955
_diffrn_reflns_theta_min         2.553
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.9
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  52.00   0.50    3.20    --  -14.97  30.00  30.00  186
  2  ω     41.00  80.00   0.50    3.20    --   16.22  45.00 -30.00   78
  3  ω     -3.00  22.00   0.50    3.20    --   16.22  45.00 -30.00   50
  4  ω     -8.00  86.00   0.50    3.20    --   16.22  45.00 -90.00  188
  5  ω     17.00  79.00   0.50    3.20    --   16.22-138.00-177.00  124
  6  ω    -37.00  22.00   0.50    3.20    --  -14.97 -94.00 -60.00  118
  7  ω     13.00  74.00   0.50    3.20    --   16.22-131.00  -2.00  122
  8  ω     11.00  70.00   0.50    3.20    --   16.22-125.00  90.00  118
  9  ω     14.00  40.00   0.50    3.20    --   16.22 -30.00 120.00   52
 10  ω    -47.00   7.00   0.50    3.20    --   16.22 -30.00 120.00  108
 11  ω    -56.00  41.00   0.50    3.20    --   16.22 -30.00  30.00  194
 12  ω    -37.00  22.00   0.50    3.20    --  -14.97 -94.00   0.00  118
 13  ω    -47.00 -10.00   0.50    3.20    --  -14.97 125.00  90.00   74
 14  ω    -73.00 -13.00   0.50    3.20    --  -14.97 131.00  68.00  120
 15  ω    -78.00 -17.00   0.50    3.20    --  -14.97 138.00-116.00  122
 16  ω    -68.00 -37.00   0.50    3.20    --  -14.97 125.00-180.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213155000
_diffrn_orient_matrix_UB_12      0.0239518000
_diffrn_orient_matrix_UB_13      0.0458531000
_diffrn_orient_matrix_UB_21      -0.0370669000
_diffrn_orient_matrix_UB_22      0.0155400000
_diffrn_orient_matrix_UB_23      -0.0705505000
_diffrn_orient_matrix_UB_31      -0.0898117000
_diffrn_orient_matrix_UB_32      -0.0007262000
_diffrn_orient_matrix_UB_33      0.0027673000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2612
_reflns_number_total             3410
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.064
_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)+(0.0610P)²+0.5660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C1(H1A,H1B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C4(H4), C6(H6), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.68578(7) 0.57567(2) 0.61809(7) 0.0524(2) Uani 1 1 d . . . . .
O5 O 0.3787(2) 0.73212(6) 0.38107(17) 0.0498(4) Uani 1 1 d . . . . .
O6 O 0.2159(2) 0.67356(7) 0.1921(2) 0.0637(5) Uani 1 1 d . . . . .
O2 O 0.2535(3) 0.40981(7) 0.9353(2) 0.0706(5) Uani 1 1 d . . . . .
O1 O 0.0371(2) 0.47597(8) 0.8082(2) 0.0775(6) Uani 1 1 d . . . . .
O3 O 0.6921(3) 0.68886(8) 0.3279(3) 0.0800(6) Uani 1 1 d . . . . .
O4 O 0.9300(2) 0.64155(9) 0.5034(3) 0.0868(6) Uani 1 1 d . . . . .
C15 C 0.3327(3) 0.68297(8) 0.3220(2) 0.0416(5) Uani 1 1 d . . . . .
C5 C 0.4126(3) 0.52522(8) 0.6935(2) 0.0426(5) Uani 1 1 d . . . . .
C10 C 0.4350(3) 0.64025(8) 0.4382(2) 0.0413(5) Uani 1 1 d . . . . .
C8 C 0.4598(3) 0.56755(8) 0.6041(2) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.3422(3) 0.60492(8) 0.5028(2) 0.0424(5) Uani 1 1 d . . . . .
H9 H 0.214382 0.606726 0.479172 0.051 Uiso 1 1 calc R . . . .
C11 C 0.6229(3) 0.62900(9) 0.4893(3) 0.0465(5) Uani 1 1 d . . . . .
C4 C 0.5415(3) 0.48511(9) 0.7719(3) 0.0496(5) Uani 1 1 d . . . . .
H4 H 0.658881 0.485673 0.767446 0.060 Uiso 1 1 calc R . . . .
C7 C 0.1984(3) 0.48454(9) 0.7843(3) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.2348(3) 0.52480(9) 0.6997(3) 0.0496(5) Uani 1 1 d . . . . .
H6 H 0.145584 0.550934 0.648157 0.059 Uiso 1 1 calc R . . . .
C2 C 0.3274(3) 0.44525(9) 0.8613(3) 0.0511(5) Uani 1 1 d . . . . .
C16 C 0.2953(3) 0.77643(9) 0.2711(3) 0.0539(6) Uani 1 1 d . . . . .
H16A H 0.160355 0.771928 0.219686 0.065 Uiso 1 1 calc R . . . .
H16B H 0.345556 0.777367 0.190086 0.065 Uiso 1 1 calc R . . . .
C3 C 0.5007(3) 0.44426(9) 0.8564(3) 0.0557(6) Uani 1 1 d . . . . .
H3 H 0.587402 0.417465 0.907412 0.067 Uiso 1 1 calc R . . . .
C12 C 0.7662(3) 0.65350(10) 0.4438(3) 0.0561(6) Uani 1 1 d . . . . .
C1 C 0.0747(4) 0.43122(11) 0.9120(4) 0.0683(7) Uani 1 1 d . . . . .
H1A H -0.021215 0.403950 0.866504 0.082 Uiso 1 1 calc R . . . .
H1B H 0.074012 0.442383 1.012878 0.082 Uiso 1 1 calc R . . . .
C17 C 0.3419(5) 0.82708(10) 0.3650(3) 0.0750(8) Uani 1 1 d . . . . .
H17A H 0.288585 0.857126 0.295930 0.112 Uiso 1 1 calc GR . . . .
H17B H 0.475612 0.831160 0.414989 0.112 Uiso 1 1 calc GR . . . .
H17C H 0.291448 0.825677 0.444777 0.112 Uiso 1 1 calc GR . . . .
C13 C 0.8174(5) 0.71939(15) 0.2760(5) 0.1079(13) Uani 1 1 d . . . . .
H13A H 0.942262 0.703974 0.322772 0.129 Uiso 1 1 calc R . . . .
H13B H 0.773838 0.716851 0.161561 0.129 Uiso 1 1 calc R . . . .
C14 C 0.8251(6) 0.77338(16) 0.3198(6) 0.1198(14) Uani 1 1 d . . . . .
H14A H 0.883472 0.794006 0.263678 0.180 Uiso 1 1 calc GR . . . .
H14B H 0.896919 0.776750 0.431970 0.180 Uiso 1 1 calc GR . . . .
H14C H 0.700276 0.786544 0.293940 0.180 Uiso 1 1 calc GR . . . .


_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 C8 1.722(2) . ?
S1 C11 1.712(2) . ?
O5 C15 1.326(2) . ?
O5 C16 1.459(3) . ?
O6 C15 1.200(2) . ?
O2 C2 1.371(3) . ?
O2 C1 1.423(3) . ?
O1 C7 1.374(3) . ?
O1 C1 1.417(3) . ?
O3 C12 1.322(3) . ?
O3 C13 1.457(3) . ?
O4 C12 1.205(3) . ?
C15 C10 1.490(3) . ?
C5 C8 1.468(3) . ?
C5 C4 1.392(3) . ?
C5 C6 1.407(3) . ?
C10 C9 1.409(3) . ?
C10 C11 1.373(3) . ?
C8 C9 1.373(3) . ?
C9 H9 0.9300 . ?
C11 C12 1.470(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(3) . ?
C7 C6 1.364(3) . ?
C7 C2 1.376(3) . ?
C6 H6 0.9300 . ?
C2 C3 1.366(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.486(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.394(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C8 92.16(10) . . ?
C15 O5 C16 116.01(16) . . ?
C2 O2 C1 105.27(18) . . ?
C7 O1 C1 105.82(19) . . ?
C12 O3 C13 118.4(2) . . ?
O5 C15 C10 112.52(17) . . ?
O6 C15 O5 124.1(2) . . ?
O6 C15 C10 123.4(2) . . ?
C4 C5 C8 120.88(19) . . ?
C4 C5 C6 119.30(19) . . ?
C6 C5 C8 119.82(18) . . ?
C9 C10 C15 121.90(17) . . ?
C11 C10 C15 125.54(18) . . ?
C11 C10 C9 112.51(19) . . ?
C5 C8 S1 121.17(15) . . ?
C9 C8 S1 110.78(15) . . ?
C9 C8 C5 128.05(18) . . ?
C10 C9 H9 123.4 . . ?
C8 C9 C10 113.10(18) . . ?
C8 C9 H9 123.4 . . ?
C10 C11 S1 111.45(16) . . ?
C10 C11 C12 130.0(2) . . ?
C12 C11 S1 118.51(16) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 H4 118.9 . . ?
O1 C7 C2 109.44(19) . . ?
C6 C7 O1 128.0(2) . . ?
C6 C7 C2 122.6(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 H6 121.3 . . ?
O2 C2 C7 110.3(2) . . ?
C3 C2 O2 128.2(2) . . ?
C3 C2 C7 121.5(2) . . ?
O5 C16 H16A 110.2 . . ?
O5 C16 H16B 110.2 . . ?
O5 C16 C17 107.38(19) . . ?
H16A C16 H16B 108.5 . . ?
C17 C16 H16A 110.2 . . ?
C17 C16 H16B 110.2 . . ?
C4 C3 H3 121.5 . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 H3 121.5 . . ?
O3 C12 C11 111.62(19) . . ?
O4 C12 O3 124.9(2) . . ?
O4 C12 C11 123.5(2) . . ?
O2 C1 H1A 109.9 . . ?
O2 C1 H1B 109.9 . . ?
O1 C1 O2 108.7(2) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C13 H13A 109.4 . . ?
O3 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 O3 111.3(3) . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.452
