# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_aks157
_database_code_depnum_ccdc_archive 'CCDC 2299357'
loop_
_audit_author_name
_audit_author_address
mahesh
;chambrize crystallography
India
;
_audit_update_record             
;
2025-05-25 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-14
_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         'C18 H15 N O5 S'
_chemical_formula_sum            'C18 H15 N O5 S'
_chemical_formula_weight         357.37
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   5.13980(10)
_cell_length_b                   9.2922(2)
_cell_length_c                   34.4165(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1643.73(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    299.06
_cell_measurement_theta_max      25.3140
_cell_measurement_theta_min      2.2700
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68208
_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    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            11884
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.866
_diffrn_reflns_theta_min         2.270
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.06
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  32.22   0.38    4.00    --   16.22  45.00 -30.00   69
  2  ω     44.00  70.22   0.38    4.00    --   16.22  45.00 -30.00   69
  3  ω     36.00  82.36   0.38    4.00    --   16.22  45.00-120.00  122
  4  ω     -7.00  32.14   0.38    4.00    --   16.22  45.00-120.00  103
  5  ω    -63.00  74.18   0.38    4.00    --   16.22 -15.00-112.00  361
  6  ω    -56.00  40.14   0.38    4.00    --   16.22 -30.00-120.00  253
  7  ω     16.00  76.80   0.38    4.00    --   16.22-136.00-144.00  160
  8  ω    -56.00 -14.96   0.38    4.00    --  -14.97 112.00-156.00  108
  9  ω    -69.00 -10.86   0.38    4.00    --  -14.97 125.00  90.00  153
;
_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      -0.0240624000
_diffrn_orient_matrix_UB_12      0.0689606000
_diffrn_orient_matrix_UB_13      0.0080735000
_diffrn_orient_matrix_UB_21      0.0124452000
_diffrn_orient_matrix_UB_22      -0.0291422000
_diffrn_orient_matrix_UB_23      0.0189664000
_diffrn_orient_matrix_UB_31      0.1352690000
_diffrn_orient_matrix_UB_32      0.0149116000
_diffrn_orient_matrix_UB_33      -0.0002979000
_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         0.626
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                2654
_reflns_number_total             3339
_reflns_odcompleteness_completeness 99.61
_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         0.135
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.053
_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)+(0.0458P)²+0.0962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0994
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 1.03618(18) 0.46678(10) 0.61279(3) 0.0763(3) Uani 1 1 d . . . . .
O5 O 0.1526(4) 0.9694(2) 0.71896(6) 0.0731(6) Uani 1 1 d . . . . .
O3 O 0.8852(5) 0.7789(2) 0.62047(7) 0.0801(7) Uani 1 1 d . . . . .
N1 N 0.8391(5) 0.5477(3) 0.64510(7) 0.0600(7) Uani 1 1 d . . . . .
O2 O 1.2624(4) 0.5542(3) 0.60975(7) 0.1015(10) Uani 1 1 d . . . . .
O4 O 0.6698(6) 0.3541(2) 0.68125(7) 0.0928(9) Uani 1 1 d . . . . .
O1 O 1.0533(7) 0.3210(3) 0.62471(7) 0.1145(11) Uani 1 1 d . . . . .
C4 C 0.5871(6) 0.7264(3) 0.67304(7) 0.0476(6) Uani 1 1 d . . . . .
C3 C 0.4624(6) 0.8523(3) 0.68324(8) 0.0482(6) Uani 1 1 d . . . . .
C10 C 0.2696(6) 0.8423(3) 0.71133(8) 0.0549(7) Uani 1 1 d . . . . .
C5 C 0.7856(6) 0.6984(3) 0.64311(8) 0.0555(7) Uani 1 1 d . . . . .
C11 C 0.8658(6) 0.4761(3) 0.56896(8) 0.0564(7) Uani 1 1 d . . . . .
C7 C 0.5228(6) 0.5970(3) 0.69106(8) 0.0530(7) Uani 1 1 d . . . . .
C6 C 0.6741(7) 0.4801(3) 0.67379(8) 0.0635(8) Uani 1 1 d . . . . .
C8 C 0.3302(7) 0.5902(3) 0.71894(8) 0.0645(9) Uani 1 1 d . . . . .
H8 H 0.287191 0.502788 0.730405 0.077 Uiso 1 1 calc R . . . .
C2 C 0.4796(6) 1.0058(3) 0.66911(9) 0.0603(8) Uani 1 1 d . . . . .
H2 H 0.650489 1.045744 0.675699 0.072 Uiso 1 1 calc R . . . .
C14 C 0.6030(7) 0.4841(3) 0.49858(9) 0.0649(8) Uani 1 1 d . . . . .
C12 C 0.6728(7) 0.3776(3) 0.56119(9) 0.0658(9) Uani 1 1 d . . . . .
H12 H 0.630006 0.307854 0.579472 0.079 Uiso 1 1 calc R . . . .
C9 C 0.2028(7) 0.7139(3) 0.72957(8) 0.0649(8) Uani 1 1 d . . . . .
H9 H 0.074346 0.711918 0.748584 0.078 Uiso 1 1 calc R . . . .
C13 C 0.5433(7) 0.3830(4) 0.52617(9) 0.0699(9) Uani 1 1 d . . . . .
H13 H 0.412435 0.316456 0.521130 0.084 Uiso 1 1 calc R . . . .
C15 C 0.7978(7) 0.5810(3) 0.50670(10) 0.0755(10) Uani 1 1 d . . . . .
H15 H 0.843222 0.649276 0.488160 0.091 Uiso 1 1 calc R . . . .
C16 C 0.9277(7) 0.5788(3) 0.54193(10) 0.0712(9) Uani 1 1 d . . . . .
H16 H 1.056053 0.646572 0.547215 0.085 Uiso 1 1 calc R . . . .
C1 C 0.2696(7) 1.0774(3) 0.69426(10) 0.0754(10) Uani 1 1 d . . . . .
H1A H 0.346652 1.152611 0.710050 0.090 Uiso 1 1 calc R . . . .
H1B H 0.137832 1.120592 0.677790 0.090 Uiso 1 1 calc R . . . .
C17 C 0.4598(10) 0.4888(5) 0.46009(10) 0.1033(13) Uani 1 1 d . . . . .
H17A H 0.521384 0.412546 0.443673 0.155 Uiso 1 1 calc GR . . . .
H17B H 0.490808 0.579744 0.447688 0.155 Uiso 1 1 calc GR . . . .
H17C H 0.276684 0.477095 0.464545 0.155 Uiso 1 1 calc GR . . . .
C18 C 0.4304(10) 1.0238(4) 0.62654(11) 0.1039(15) Uani 1 1 d . . . . .
H18A H 0.568066 0.978825 0.612109 0.156 Uiso 1 1 calc GR . . . .
H18B H 0.423940 1.124384 0.620298 0.156 Uiso 1 1 calc GR . . . .
H18C H 0.267536 0.979553 0.619883 0.156 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 N1 1.681(2) . ?
S1 O2 1.422(3) . ?
S1 O1 1.418(3) . ?
S1 C11 1.746(3) . ?
O5 C10 1.351(3) . ?
O5 C1 1.446(4) . ?
O3 C5 1.195(3) . ?
N1 C5 1.429(4) . ?
N1 C6 1.445(4) . ?
O4 C6 1.199(3) . ?
C4 C3 1.380(3) . ?
C4 C5 1.473(4) . ?
C4 C7 1.393(4) . ?
C3 C10 1.388(4) . ?
C3 C2 1.509(3) . ?
C10 C9 1.391(4) . ?
C11 C12 1.375(4) . ?
C11 C16 1.370(4) . ?
C7 C6 1.462(4) . ?
C7 C8 1.380(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(4) . ?
C2 H2 0.9800 . ?
C2 C1 1.535(4) . ?
C2 C18 1.496(4) . ?
C14 C13 1.371(4) . ?
C14 C15 1.375(4) . ?
C14 C17 1.516(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
N1 S1 C11 104.30(13) . . ?
O2 S1 N1 106.63(14) . . ?
O2 S1 C11 108.55(16) . . ?
O1 S1 N1 105.85(16) . . ?
O1 S1 O2 121.07(19) . . ?
O1 S1 C11 109.15(16) . . ?
C10 O5 C1 107.9(2) . . ?
C5 N1 S1 121.5(2) . . ?
C5 N1 C6 110.2(2) . . ?
C6 N1 S1 127.7(2) . . ?
C3 C4 C5 130.5(2) . . ?
C3 C4 C7 120.6(3) . . ?
C7 C4 C5 108.8(2) . . ?
C4 C3 C10 116.9(2) . . ?
C4 C3 C2 133.8(3) . . ?
C10 C3 C2 109.2(2) . . ?
O5 C10 C3 113.3(2) . . ?
O5 C10 C9 123.5(3) . . ?
C3 C10 C9 123.2(3) . . ?
O3 C5 N1 124.2(3) . . ?
O3 C5 C4 129.9(3) . . ?
N1 C5 C4 105.8(2) . . ?
C12 C11 S1 119.8(2) . . ?
C16 C11 S1 120.3(3) . . ?
C16 C11 C12 119.9(3) . . ?
C4 C7 C6 109.5(3) . . ?
C8 C7 C4 121.3(3) . . ?
C8 C7 C6 129.1(3) . . ?
N1 C6 C7 105.5(2) . . ?
O4 C6 N1 125.5(3) . . ?
O4 C6 C7 129.0(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C3 C2 H2 109.6 . . ?
C3 C2 C1 100.8(2) . . ?
C1 C2 H2 109.6 . . ?
C18 C2 C3 114.3(3) . . ?
C18 C2 H2 109.6 . . ?
C18 C2 C1 112.6(3) . . ?
C13 C14 C15 118.1(3) . . ?
C13 C14 C17 121.1(3) . . ?
C15 C14 C17 120.8(3) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9 120.6 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 119.5(3) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O5 C1 C2 108.8(2) . . ?
O5 C1 H1A 109.9 . . ?
O5 C1 H1B 109.9 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.641
