# Supplementary Information (SI) for Analytical Methods.
# 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_ex-anph_auto
_database_code_depnum_ccdc_archive 'CCDC 2416231'
loop_
_audit_author_name
_audit_author_address
'Sushil Kumar'
;UPES Dehradun
India
;
_audit_update_record             
;
2025-01-10 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2024-11-12
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 N S'
_chemical_formula_sum            'C27 H19 N S'
_chemical_formula_weight         389.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N 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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9312(5)
_cell_length_b                   10.4343(7)
_cell_length_c                   12.5929(7)
_cell_angle_alpha                73.098(5)
_cell_angle_beta                 70.992(5)
_cell_angle_gamma                65.822(6)
_cell_volume                     995.24(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8841
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7160
_cell_measurement_theta_min      3.4590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15707
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.133
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -54.00   0.50    6.77    --   -9.32 167.00 103.00   54
  2  ω    -48.00 -23.00   0.50    6.77    --   -9.32 116.00 -42.00   50
  3  ω      0.00  25.00   0.50    6.77    --    9.60-116.00-131.00   50
  4  ω     48.00  73.00   0.50    6.77    --    9.60-167.00  83.00   50
  5  ω    -27.00   7.00   0.50    6.77    --   -9.32  57.00  60.00   68
  6  ω     24.00  50.00   0.50    6.77    --   -9.32  38.00 -90.00   52
  7  ω    -23.00  13.00   0.50    6.77    --   -9.32  38.00 -90.00   72
  8  ω     16.00  53.00   0.50    6.77    --   -9.32  57.00  60.00   74
  9  ω    -18.00  56.00   0.50    6.77    --   -9.32  19.00   0.00  148
 10  ω    -56.00 -31.00   0.50    6.77    --   -9.32 125.00  60.00   50
 11  ω     -7.00  22.00   0.50    6.77    --    9.60 -99.00 -30.00   58
 12  ω    -54.00  22.00   0.50    6.77    --    9.60 -38.00 150.00  152
 13  ω      7.00  32.00   0.50    6.77    --    9.60-125.00 -30.00   50
 14  ω    -34.00  -9.00   0.50    6.77    --    9.60 128.00-115.72   50
 15  ω    -12.00  36.00   0.50    6.77    --    9.60 -99.00 -90.00   96
 16  ω     14.00  54.00   0.50    6.77    --    9.60-125.00-150.00   80
 17  ω    -31.00  -5.00   0.50    6.77    --    9.60 119.00 156.77   52
 18  ω    -16.00  33.00   0.50    6.77    --    9.60  77.00 120.00   98
 19  ω      9.00  79.00   0.50    6.77    --    9.60  19.00  90.00  140
 20  ω    -11.00  32.00   0.50    6.77    --    9.60  77.00 -30.00   86
 21  ω    -10.00  16.00   0.50    6.77    --    9.60 -77.00 120.00   52
 22  ω    -53.00  12.00   0.50    6.77    --    9.60 -38.00  90.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, 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      -0.0193182000
_diffrn_orient_matrix_UB_12      0.0719236000
_diffrn_orient_matrix_UB_13      0.0034940000
_diffrn_orient_matrix_UB_21      0.0328320000
_diffrn_orient_matrix_UB_22      0.0154075000
_diffrn_orient_matrix_UB_23      -0.0597875000
_diffrn_orient_matrix_UB_31      -0.0811001000
_diffrn_orient_matrix_UB_32      0.0182494000
_diffrn_orient_matrix_UB_33      -0.0091896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2988
_reflns_number_total             4120
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.1055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1411
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C20(H20), C27(H27), C11(H11), C15(H15), C5(H5), C14(H14), C12(H12),
 C17(H17), C2(H2), C26(H26), C19(H19), C23(H23), C13(H13), C25(H25), C18(H18),
 C6(H6), C1(H1), C24(H24)
;
_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 0.39696(6) 0.69002(6) 0.87658(4) 0.0640(2) Uani 1 1 d . . . . .
N1 N 0.67136(17) 0.66946(17) 0.67521(12) 0.0502(4) Uani 1 1 d . . . . .
C10 C 0.73339(19) 0.5724(2) 0.50806(14) 0.0444(4) Uani 1 1 d . . . . .
C8 C 0.70281(19) 0.4190(2) 0.40671(15) 0.0442(4) Uani 1 1 d . . . . .
C16 C 0.7199(2) 0.67168(18) 0.77096(14) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.75819(19) 0.43484(19) 0.49551(14) 0.0445(4) Uani 1 1 d . . . . .
C4 C 0.6656(2) 0.6939(2) 0.42894(14) 0.0473(4) Uani 1 1 d . . . . .
C22 C 0.2603(2) 0.7653(2) 0.99778(14) 0.0478(4) Uani 1 1 d . . . . .
C21 C 0.5978(2) 0.68467(18) 0.87450(14) 0.0437(4) Uani 1 1 d . . . . .
C7 C 0.6302(2) 0.5398(2) 0.33229(15) 0.0489(4) Uani 1 1 d . . . . .
H7 H 0.593027 0.529192 0.275503 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6114(2) 0.6757(2) 0.33990(14) 0.0488(4) Uani 1 1 d . . . . .
C20 C 0.6431(2) 0.6855(2) 0.96971(16) 0.0531(5) Uani 1 1 d . . . . .
H20 H 0.564301 0.690227 1.039540 0.064 Uiso 1 1 calc R U . . .
C27 C 0.1482(2) 0.6995(2) 1.07027(15) 0.0525(5) Uani 1 1 d . . . . .
H27 H 0.155733 0.611966 1.060396 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7208(2) 0.2802(2) 0.39825(17) 0.0543(5) Uani 1 1 d . . . . .
H11 H 0.683060 0.269950 0.341554 0.065 Uiso 1 1 calc R U . . .
C15 C 0.7717(2) 0.5850(2) 0.60916(16) 0.0523(5) Uani 1 1 d . . . . .
H15 H 0.876365 0.526954 0.624700 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6491(2) 0.8339(2) 0.43157(17) 0.0585(5) Uani 1 1 d . . . . .
H5 H 0.686475 0.847912 0.486742 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8304(2) 0.3073(2) 0.57050(17) 0.0591(5) Uani 1 1 d . . . . .
H14 H 0.866636 0.313624 0.629580 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7912(2) 0.1634(2) 0.47051(19) 0.0616(5) Uani 1 1 d . . . . .
H12 H 0.802747 0.073473 0.463125 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8794(2) 0.6673(2) 0.76531(17) 0.0582(5) Uani 1 1 d . . . . .
H17 H 0.959756 0.662099 0.696164 0.070 Uiso 1 1 calc R U . . .
C2 C 0.5363(3) 0.7989(2) 0.26373(16) 0.0633(6) Uani 1 1 d . . . . .
H2 H 0.497866 0.788796 0.207375 0.076 Uiso 1 1 calc R U . . .
C26 C 0.0253(2) 0.7641(3) 1.15720(17) 0.0652(6) Uani 1 1 d . . . . .
H26 H -0.052093 0.721079 1.204557 0.078 Uiso 1 1 calc R U . . .
C19 C 0.8029(3) 0.6793(2) 0.96228(18) 0.0636(6) Uani 1 1 d . . . . .
H19 H 0.830871 0.681086 1.026659 0.076 Uiso 1 1 calc R U . . .
C23 C 0.2493(3) 0.8939(2) 1.01548(18) 0.0634(5) Uani 1 1 d . . . . .
H23 H 0.323304 0.939532 0.966657 0.076 Uiso 1 1 calc R U . . .
C13 C 0.8473(3) 0.1776(2) 0.55730(19) 0.0669(6) Uani 1 1 d . . . . .
H13 H 0.896833 0.096300 0.606511 0.080 Uiso 1 1 calc R U . . .
C25 C 0.0160(3) 0.8911(3) 1.17455(19) 0.0694(6) Uani 1 1 d . . . . .
H25 H -0.067269 0.933851 1.233530 0.083 Uiso 1 1 calc R U . . .
C18 C 0.9208(2) 0.6706(2) 0.86035(19) 0.0668(6) Uani 1 1 d . . . . .
H18 H 1.028668 0.666818 0.855366 0.080 Uiso 1 1 calc R U . . .
C6 C 0.5805(3) 0.9473(2) 0.35573(19) 0.0701(6) Uani 1 1 d . . . . .
H6 H 0.573075 1.037797 0.358710 0.084 Uiso 1 1 calc R U . . .
C1 C 0.5197(3) 0.9309(2) 0.27187(19) 0.0725(6) Uani 1 1 d . . . . .
H1 H 0.468383 1.010678 0.222262 0.087 Uiso 1 1 calc R U . . .
C24 C 0.1292(3) 0.9547(2) 1.10504(19) 0.0694(6) Uani 1 1 d . . . . .
H24 H 0.125192 1.039387 1.118239 0.083 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 C22 1.7702(18) . ?
S1 C21 1.7635(17) . ?
N1 C16 1.417(2) . ?
N1 C15 1.251(2) . ?
C10 C9 1.408(2) . ?
C10 C4 1.413(2) . ?
C10 C15 1.474(2) . ?
C8 C9 1.434(2) . ?
C8 C7 1.388(3) . ?
C8 C11 1.422(2) . ?
C16 C21 1.401(2) . ?
C16 C17 1.385(2) . ?
C9 C14 1.429(3) . ?
C4 C3 1.442(2) . ?
C4 C5 1.417(3) . ?
C22 C27 1.382(2) . ?
C22 C23 1.383(3) . ?
C21 C20 1.388(2) . ?
C7 C3 1.387(2) . ?
C3 C2 1.421(3) . ?
C20 C19 1.375(3) . ?
C27 C26 1.378(3) . ?
C11 C12 1.345(3) . ?
C5 C6 1.348(3) . ?
C14 C13 1.353(3) . ?
C12 C13 1.407(3) . ?
C17 C18 1.376(3) . ?
C2 C1 1.354(3) . ?
C26 C25 1.370(3) . ?
C19 C18 1.369(3) . ?
C23 C24 1.377(3) . ?
C25 C24 1.366(3) . ?
C6 C1 1.412(3) . ?

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
C21 S1 C22 104.78(8) . . ?
C15 N1 C16 119.11(15) . . ?
C9 C10 C4 120.44(15) . . ?
C9 C10 C15 117.75(16) . . ?
C4 C10 C15 121.73(16) . . ?
C7 C8 C9 119.18(16) . . ?
C7 C8 C11 121.56(16) . . ?
C11 C8 C9 119.25(17) . . ?
C21 C16 N1 117.87(14) . . ?
C17 C16 N1 123.01(15) . . ?
C17 C16 C21 119.06(15) . . ?
C10 C9 C8 119.66(16) . . ?
C10 C9 C14 123.33(16) . . ?
C14 C9 C8 116.96(17) . . ?
C10 C4 C3 118.95(16) . . ?
C10 C4 C5 123.31(17) . . ?
C5 C4 C3 117.74(18) . . ?
C27 C22 S1 117.80(15) . . ?
C27 C22 C23 119.17(17) . . ?
C23 C22 S1 122.65(14) . . ?
C16 C21 S1 117.07(12) . . ?
C20 C21 S1 124.00(13) . . ?
C20 C21 C16 118.84(15) . . ?
C3 C7 C8 122.12(16) . . ?
C7 C3 C4 119.49(17) . . ?
C7 C3 C2 121.79(17) . . ?
C2 C3 C4 118.70(18) . . ?
C19 C20 C21 120.95(17) . . ?
C26 C27 C22 119.78(19) . . ?
C12 C11 C8 121.37(18) . . ?
N1 C15 C10 123.65(17) . . ?
C6 C5 C4 121.3(2) . . ?
C13 C14 C9 121.34(18) . . ?
C11 C12 C13 119.85(19) . . ?
C18 C17 C16 121.06(17) . . ?
C1 C2 C3 121.1(2) . . ?
C25 C26 C27 120.63(19) . . ?
C18 C19 C20 120.16(17) . . ?
C24 C23 C22 120.33(19) . . ?
C14 C13 C12 121.2(2) . . ?
C24 C25 C26 119.9(2) . . ?
C19 C18 C17 119.85(17) . . ?
C5 C6 C1 121.1(2) . . ?
C2 C1 C6 119.9(2) . . ?
C25 C24 C23 120.2(2) . . ?

_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.633
