# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_sd_47_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2118371'
loop_
_audit_author_name
_audit_author_address
'PROF. INDUBHUSAN DEB'
;CSIR Indian institute of chemical biology
India
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        9-tosyl-9H-xanthene
_chemical_formula_moiety         'C20 H16 O3 S'
_chemical_formula_sum            'C20 H16 O3 S'
_chemical_formula_weight         336.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   8.7563(10)
_cell_length_b                   5.3376(7)
_cell_length_c                   33.444(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.906(4)
_cell_angle_gamma                90
_cell_volume                     1557.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.43
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.693
_shelx_estimated_absorpt_T_min   0.438
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1088 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.6590. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            21860
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.530
_diffrn_reflns_theta_max         66.530
_diffrn_reflns_theta_min         2.652
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2667
_reflns_number_total             2690
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+0.7790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C3(H3), C9(H9), C10(H10), C6(H6), C11(H11), C15(H15),
 C4(H4), C5(H5), C16(H16), C12(H12)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.47627(4) 0.58962(7) 0.65196(2) 0.01559(17) Uani 1 1 d . . . . .
O3 O 0.46989(13) 0.8532(2) 0.64212(4) 0.0208(3) Uani 1 1 d . . . . .
O1 O 0.58200(13) 0.8283(2) 0.55548(4) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.33631(13) 0.4634(2) 0.65993(4) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.71239(19) 0.7383(3) 0.57718(5) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.55569(19) 0.4246(3) 0.61043(5) 0.0164(4) Uani 1 1 d . . . . .
H1 H 0.567172 0.242257 0.616845 0.020 Uiso 1 1 calc R U . . .
C2 C 0.70803(19) 0.5346(3) 0.60285(5) 0.0171(4) Uani 1 1 d . . . . .
C14 C 0.60846(19) 0.5512(3) 0.69446(5) 0.0164(4) Uani 1 1 d . . . . .
C19 C 0.59479(19) 0.3445(3) 0.71920(5) 0.0191(4) Uani 1 1 d . . . . .
H19 H 0.522003 0.216800 0.711993 0.023 Uiso 1 1 calc R U . . .
C13 C 0.44176(19) 0.4607(3) 0.57459(5) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.45894(19) 0.6653(3) 0.54961(5) 0.0176(4) Uani 1 1 d . . . . .
C18 C 0.6894(2) 0.3279(3) 0.75465(5) 0.0200(4) Uani 1 1 d . . . . .
H18 H 0.681996 0.185847 0.771491 0.024 Uiso 1 1 calc R U . . .
C17 C 0.79492(19) 0.5157(3) 0.76593(5) 0.0203(4) Uani 1 1 d . . . . .
C3 C 0.8458(2) 0.4434(3) 0.62133(5) 0.0205(4) Uani 1 1 d . . . . .
H3 H 0.844847 0.301621 0.638485 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3541(2) 0.7146(3) 0.51698(5) 0.0197(4) Uani 1 1 d . . . . .
H9 H 0.366667 0.855766 0.500281 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2308(2) 0.5537(3) 0.50928(5) 0.0214(4) Uani 1 1 d . . . . .
H10 H 0.157445 0.586309 0.487308 0.026 Uiso 1 1 calc R U . . .
C6 C 0.8491(2) 0.8592(4) 0.57142(5) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.849902 1.002727 0.554645 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2134(2) 0.3448(4) 0.53340(5) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.129625 0.233759 0.527536 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7172(2) 0.7355(3) 0.70416(5) 0.0197(4) Uani 1 1 d . . . . .
H15 H 0.728612 0.872431 0.686511 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9841(2) 0.5571(4) 0.61498(5) 0.0237(4) Uani 1 1 d . . . . .
H4 H 1.077561 0.491711 0.627253 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9848(2) 0.7672(4) 0.59056(6) 0.0251(4) Uani 1 1 d . . . . .
H5 H 1.078923 0.848929 0.586877 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8091(2) 0.7171(3) 0.73996(5) 0.0215(4) Uani 1 1 d . . . . .
H16 H 0.882890 0.843803 0.746890 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3182(2) 0.2991(3) 0.56595(5) 0.0194(4) Uani 1 1 d . . . . .
H12 H 0.305948 0.157013 0.582482 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8867(2) 0.5049(4) 0.80603(5) 0.0271(4) Uani 1 1 d . . . . .
H20A H 0.821809 0.554916 0.827131 0.041 Uiso 1 1 calc R U . . .
H20B H 0.974262 0.619170 0.805989 0.041 Uiso 1 1 calc R U . . .
H20C H 0.923721 0.333615 0.811095 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4447(13) . ?
S1 O2 1.4432(12) . ?
S1 C1 1.8313(17) . ?
S1 C14 1.7666(18) . ?
O1 C7 1.385(2) . ?
O1 C8 1.386(2) . ?
C7 C2 1.388(2) . ?
C7 C6 1.387(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.499(2) . ?
C1 C13 1.505(2) . ?
C2 C3 1.395(2) . ?
C14 C19 1.390(2) . ?
C14 C15 1.388(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.390(2) . ?
C13 C8 1.391(2) . ?
C13 C12 1.394(2) . ?
C8 C9 1.390(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.393(3) . ?
C17 C16 1.394(3) . ?
C17 C20 1.504(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O3 S1 C1 107.78(7) . . ?
O3 S1 C14 107.84(8) . . ?
O2 S1 O3 118.67(7) . . ?
O2 S1 C1 107.41(8) . . ?
O2 S1 C14 107.78(8) . . ?
C14 S1 C1 106.81(8) . . ?
C7 O1 C8 116.90(13) . . ?
O1 C7 C2 122.05(15) . . ?
O1 C7 C6 116.62(15) . . ?
C6 C7 C2 121.32(16) . . ?
S1 C1 H1 110.1 . . ?
C2 C1 S1 109.95(11) . . ?
C2 C1 H1 110.1 . . ?
C2 C1 C13 110.75(14) . . ?
C13 C1 S1 105.89(11) . . ?
C13 C1 H1 110.1 . . ?
C7 C2 C1 118.91(15) . . ?
C7 C2 C3 118.62(16) . . ?
C3 C2 C1 122.45(16) . . ?
C19 C14 S1 119.16(13) . . ?
C15 C14 S1 119.66(13) . . ?
C15 C14 C19 121.03(16) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 C14 118.88(16) . . ?
C18 C19 H19 120.6 . . ?
C8 C13 C1 118.71(15) . . ?
C8 C13 C12 118.89(16) . . ?
C12 C13 C1 122.39(15) . . ?
O1 C8 C13 122.04(15) . . ?
O1 C8 C9 116.48(15) . . ?
C9 C8 C13 121.47(16) . . ?
C19 C18 H18 119.4 . . ?
C19 C18 C17 121.21(16) . . ?
C17 C18 H18 119.4 . . ?
C18 C17 C16 118.59(16) . . ?
C18 C17 C20 120.35(17) . . ?
C16 C17 C20 121.02(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.83(17) . . ?
C4 C3 H3 119.6 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.70(16) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.73(16) . . ?
C11 C10 H10 119.6 . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 119.03(17) . . ?
C5 C6 H6 120.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.88(17) . . ?
C12 C11 H11 120.1 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.14(16) . . ?
C16 C15 H15 120.4 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.44(16) . . ?
C5 C4 H4 120.3 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.66(17) . . ?
C4 C5 H5 119.7 . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.05(16) . . ?
C15 C16 H16 119.5 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.31(16) . . ?
C11 C12 H12 119.8 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
S1 C1 C2 C7 -87.19(16) . . . . ?
S1 C1 C2 C3 91.35(17) . . . . ?
S1 C1 C13 C8 90.95(16) . . . . ?
S1 C1 C13 C12 -87.86(17) . . . . ?
S1 C14 C19 C18 -173.77(13) . . . . ?
S1 C14 C15 C16 172.85(13) . . . . ?
O3 S1 C1 C2 55.54(13) . . . . ?
O3 S1 C1 C13 -64.14(13) . . . . ?
O3 S1 C14 C19 155.31(13) . . . . ?
O3 S1 C14 C15 -20.27(16) . . . . ?
O1 C7 C2 C1 -6.2(2) . . . . ?
O1 C7 C2 C3 175.25(15) . . . . ?
O1 C7 C6 C5 -176.13(15) . . . . ?
O1 C8 C9 C10 178.57(15) . . . . ?
O2 S1 C1 C2 -175.52(11) . . . . ?
O2 S1 C1 C13 64.81(12) . . . . ?
O2 S1 C14 C19 26.08(16) . . . . ?
O2 S1 C14 C15 -149.51(14) . . . . ?
C7 O1 C8 C13 22.1(2) . . . . ?
C7 O1 C8 C9 -156.98(14) . . . . ?
C7 C2 C3 C4 1.5(3) . . . . ?
C7 C6 C5 C4 0.2(3) . . . . ?
C1 S1 C14 C19 -89.08(15) . . . . ?
C1 S1 C14 C15 95.34(15) . . . . ?
C1 C2 C3 C4 -177.07(15) . . . . ?
C1 C13 C8 O1 3.6(2) . . . . ?
C1 C13 C8 C9 -177.36(15) . . . . ?
C1 C13 C12 C11 177.76(15) . . . . ?
C2 C7 C6 C5 2.7(3) . . . . ?
C2 C1 C13 C8 -28.2(2) . . . . ?
C2 C1 C13 C12 152.99(15) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C14 S1 C1 C2 -60.11(13) . . . . ?
C14 S1 C1 C13 -179.79(11) . . . . ?
C14 C19 C18 C17 1.1(2) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C19 C14 C15 C16 -2.7(3) . . . . ?
C19 C18 C17 C16 -2.9(3) . . . . ?
C19 C18 C17 C20 174.76(16) . . . . ?
C13 C1 C2 C7 29.5(2) . . . . ?
C13 C1 C2 C3 -151.98(16) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C8 O1 C7 C2 -20.8(2) . . . . ?
C8 O1 C7 C6 157.95(15) . . . . ?
C8 C13 C12 C11 -1.0(2) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C18 C17 C16 C15 2.0(3) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C6 C7 C2 C1 175.12(15) . . . . ?
C6 C7 C2 C3 -3.5(2) . . . . ?
C15 C14 C19 C18 1.8(3) . . . . ?
C12 C13 C8 O1 -177.56(14) . . . . ?
C12 C13 C8 C9 1.5(2) . . . . ?
C20 C17 C16 C15 -175.67(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pet ether-chloroform'
