# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2ffhcr
_database_code_depnum_ccdc_archive 'CCDC 2247294'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c00306 2023
loop_
_audit_author_name
_audit_author_address
Manas
;IIT Jammu
India
;
_audit_update_record             
;
2023-03-08 deposited with the CCDC.	2023-11-20 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         'C12 H12 O3 S'
_chemical_formula_sum            'C12 H12 O3 S'
_chemical_formula_weight         236.28

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.6096(16)
_cell_length_b                   8.7670(15)
_cell_length_c                   14.390(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.067(6)
_cell_angle_gamma                90
_cell_volume                     1176.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9402
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      33.68

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.264
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5528
_exptl_absorpt_correction_T_max  0.5966
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44612
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         33.849
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4326
_reflns_number_gt                3819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0693P)²+0.1695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4326
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.88997(3) 0.89978(3) 0.36612(2) 0.04460(10) Uani 1 1 d . . . . .
O1 O 0.62769(8) 0.88077(8) 0.46830(5) 0.03394(16) Uani 1 1 d . . . . .
O2 O 0.55561(8) 0.54286(9) 0.39430(6) 0.03672(17) Uani 1 1 d . . . . .
O3 O 0.72738(10) 0.36452(8) 0.41616(7) 0.04324(19) Uani 1 1 d . . . . .
C1 C 0.51035(9) 0.85821(9) 0.30378(6) 0.02386(15) Uani 1 1 d . . . . .
C2 C 0.51156(10) 0.79067(11) 0.21636(6) 0.03043(18) Uani 1 1 d . . . . .
H2A H 0.591681 0.731606 0.210141 0.037 Uiso 1 1 calc R U . . .
C3 C 0.39533(12) 0.80994(14) 0.13836(7) 0.0398(2) Uani 1 1 d . . . . .
H3A H 0.394826 0.761961 0.079089 0.048 Uiso 1 1 calc R U . . .
C4 C 0.27999(12) 0.89916(14) 0.14689(8) 0.0417(2) Uani 1 1 d . . . . .
H4A H 0.200346 0.911641 0.093480 0.050 Uiso 1 1 calc R U . . .
C5 C 0.28030(10) 0.97038(14) 0.23317(8) 0.0386(2) Uani 1 1 d . . . . .
H5A H 0.202477 1.034147 0.238080 0.046 Uiso 1 1 calc R U . . .
C6 C 0.39438(10) 0.94835(11) 0.31220(7) 0.03046(17) Uani 1 1 d . . . . .
H6A H 0.393502 0.994459 0.371794 0.037 Uiso 1 1 calc R U . . .
C7 C 0.62985(9) 0.83418(9) 0.38918(5) 0.02352(15) Uani 1 1 d . . . . .
C8 C 0.76725(8) 0.76030(10) 0.37698(5) 0.02471(15) Uani 1 1 d . . . . .
C9 C 1.04847(15) 0.7919(3) 0.36831(17) 0.0840(6) Uani 1 1 d . . . . .
H9A H 1.126827 0.861402 0.364576 0.126 Uiso 1 1 calc R U . . .
H9B H 1.030392 0.721975 0.313565 0.126 Uiso 1 1 calc R U . . .
H9C H 1.075129 0.733282 0.427975 0.126 Uiso 1 1 calc R U . . .
C10 C 0.79045(9) 0.60945(10) 0.38232(6) 0.02812(17) Uani 1 1 d . . . . .
H10A H 0.879918 0.569431 0.376711 0.034 Uiso 1 1 calc R U . . .
C11 C 0.67754(10) 0.50634(10) 0.39682(6) 0.02855(17) Uani 1 1 d . . . . .
C12 C 0.62325(18) 0.25853(14) 0.43777(14) 0.0632(4) Uani 1 1 d . . . . .
H12A H 0.667978 0.158180 0.452805 0.095 Uiso 1 1 calc R U . . .
H12B H 0.541262 0.249890 0.382152 0.095 Uiso 1 1 calc R U . . .
H12C H 0.590293 0.296064 0.492911 0.095 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 C8 1.7321(9) . ?
S1 C9 1.7865(17) . ?
O1 C7 1.2145(10) . ?
O2 C11 1.2067(12) . ?
O3 C11 1.3371(11) . ?
O3 C12 1.4535(16) . ?
C1 C2 1.3930(12) . ?
C1 C6 1.3952(12) . ?
C1 C7 1.4790(11) . ?
C2 C3 1.3879(13) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3862(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3891(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3879(13) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.5187(12) . ?
C8 C10 1.3403(12) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4656(13) . ?
C10 H10A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C8 S1 C9 102.77(7) . . ?
C11 O3 C12 114.11(10) . . ?
C2 C1 C6 120.08(8) . . ?
C2 C1 C7 120.97(8) . . ?
C6 C1 C7 118.94(7) . . ?
C3 C2 C1 119.79(9) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 120.05(10) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.31(9) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.96(9) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 119.75(9) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
O1 C7 C1 122.97(8) . . ?
O1 C7 C8 117.73(7) . . ?
C1 C7 C8 119.08(7) . . ?
C10 C8 C7 123.46(8) . . ?
C10 C8 S1 126.47(7) . . ?
C7 C8 S1 109.84(6) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 119.88(8) . . ?
C8 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
O2 C11 O3 123.30(9) . . ?
O2 C11 C10 125.39(8) . . ?
O3 C11 C10 111.29(8) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 C1 C2 C3 -1.74(14) . . . . ?
C7 C1 C2 C3 177.34(9) . . . . ?
C1 C2 C3 C4 1.55(16) . . . . ?
C2 C3 C4 C5 0.37(18) . . . . ?
C3 C4 C5 C6 -2.10(17) . . . . ?
C4 C5 C6 C1 1.89(16) . . . . ?
C2 C1 C6 C5 0.02(14) . . . . ?
C7 C1 C6 C5 -179.08(9) . . . . ?
C2 C1 C7 O1 -173.93(9) . . . . ?
C6 C1 C7 O1 5.16(13) . . . . ?
C2 C1 C7 C8 11.57(11) . . . . ?
C6 C1 C7 C8 -169.35(8) . . . . ?
O1 C7 C8 C10 94.82(10) . . . . ?
C1 C7 C8 C10 -90.39(10) . . . . ?
O1 C7 C8 S1 -80.06(8) . . . . ?
C1 C7 C8 S1 94.73(7) . . . . ?
C9 S1 C8 C10 -1.89(12) . . . . ?
C9 S1 C8 C7 172.80(9) . . . . ?
C7 C8 C10 C11 2.54(13) . . . . ?
S1 C8 C10 C11 176.56(6) . . . . ?
C12 O3 C11 O2 -2.32(16) . . . . ?
C12 O3 C11 C10 176.03(10) . . . . ?
C8 C10 C11 O2 8.65(14) . . . . ?
C8 C10 C11 O3 -169.66(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12A O1 0.98 2.48 3.3397(15) 146.1 1_545 yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052



