# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_KB327_0m
_database_code_depnum_ccdc_archive 'CCDC 2270963'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-06-20 deposited with the CCDC.	2023-07-18 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         'C26 H15 N O2 S'
_chemical_formula_sum            'C26 H15 N O2 S'
_chemical_formula_weight         405.45

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.0366(6)
_cell_length_b                   9.9845(6)
_cell_length_c                   12.3996(8)
_cell_angle_alpha                93.071(2)
_cell_angle_beta                 104.114(2)
_cell_angle_gamma                110.0625(17)
_cell_volume                     1007.52(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8021
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4381
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18080
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.605
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4584
_reflns_number_gt                3435
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4584
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_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 0.18194(5) 0.45461(5) 0.01574(4) 0.05072(19) Uani 1 1 d . . . . .
O1 O 0.8598(3) 1.12858(16) 0.44151(16) 0.1006(6) Uani 1 1 d . . . . .
O2 O 0.41628(18) 0.30773(13) 0.06207(12) 0.0638(4) Uani 1 1 d . . . . .
N2 N 0.0237(3) 0.2441(2) 0.13515(19) 0.0854(6) Uani 1 1 d . . . . .
C1 C 0.1781(3) 0.9403(2) 0.13839(19) 0.0670(6) Uani 1 1 d . . . . .
H1 H 0.122794 1.004056 0.132051 0.080 Uiso 1 1 calc R U . . .
C2 C 0.1365(2) 0.8280(2) 0.19842(17) 0.0627(5) Uani 1 1 d . . . . .
H3 H 0.051315 0.814448 0.231360 0.075 Uiso 1 1 calc R U . . .
C3 C 0.2205(2) 0.7360(2) 0.20974(16) 0.0521(4) Uani 1 1 d . . . . .
H4 H 0.192369 0.660939 0.251211 0.063 Uiso 1 1 calc R U . . .
C4 C 0.34644(19) 0.75301(17) 0.16044(13) 0.0386(4) Uani 1 1 d . . . . .
C5 C 0.60913(19) 0.71339(16) 0.26065(13) 0.0356(3) Uani 1 1 d . . . . .
C6 C 0.5855(2) 0.75627(18) 0.37418(13) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.6695(2) 0.8944(2) 0.43403(15) 0.0527(5) Uani 1 1 d . . . . .
C8 C 0.6481(4) 0.9259(3) 0.53892(19) 0.0808(7) Uani 1 1 d . . . . .
H7 H 0.705678 1.017804 0.579909 0.097 Uiso 1 1 calc R U . . .
C9 C 0.5437(4) 0.8235(3) 0.5822(2) 0.0848(8) Uani 1 1 d . . . . .
H2 H 0.529858 0.846411 0.651838 0.102 Uiso 1 1 calc R U . . .
C10 C 0.7828(3) 1.0081(2) 0.38814(18) 0.0620(5) Uani 1 1 d . . . . .
C11 C 0.7973(2) 0.9702(2) 0.27770(17) 0.0543(5) Uani 1 1 d . . . . .
H5 H 0.864482 1.040945 0.246611 0.065 Uiso 1 1 calc R U . . .
C12 C 0.71903(19) 0.83915(17) 0.21934(14) 0.0413(4) Uani 1 1 d . . . . .
H6 H 0.732432 0.823343 0.148338 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4590(3) 0.6865(3) 0.52289(17) 0.0685(6) Uani 1 1 d . . . . .
H9 H 0.387098 0.617324 0.552096 0.082 Uiso 1 1 calc R U . . .
C14 C 0.4810(2) 0.6519(2) 0.41981(15) 0.0503(4) Uani 1 1 d . . . . .
H8 H 0.425872 0.558647 0.380810 0.060 Uiso 1 1 calc R U . . .
C15 C 0.69555(19) 0.60522(17) 0.27596(13) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.6313(2) 0.46996(17) 0.21041(13) 0.0387(4) Uani 1 1 d . . . . .
C17 C 0.4716(2) 0.42239(16) 0.12518(13) 0.0412(4) Uani 1 1 d . . . . .
C18 C 0.37965(18) 0.52032(16) 0.11736(12) 0.0369(4) Uani 1 1 d . . . . .
C19 C 0.0875(2) 0.3277(2) 0.08621(17) 0.0538(5) Uani 1 1 d . . . . .
C20 C 0.7194(2) 0.3770(2) 0.22575(16) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.676436 0.286540 0.182079 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8689(3) 0.4202(2) 0.30535(17) 0.0595(5) Uani 1 1 d . . . . .
H12 H 0.926990 0.358739 0.315502 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9330(2) 0.5544(2) 0.37017(17) 0.0567(5) Uani 1 1 d . . . . .
H10 H 1.034452 0.583319 0.423613 0.068 Uiso 1 1 calc R U . . .
C23 C 0.8474(2) 0.6459(2) 0.35616(15) 0.0490(4) Uani 1 1 d . . . . .
H11 H 0.891453 0.735827 0.400718 0.059 Uiso 1 1 calc R U . . .
C24 C 0.3839(2) 0.8638(2) 0.09786(17) 0.0560(5) Uani 1 1 d . . . . .
H14 H 0.465516 0.875472 0.061836 0.067 Uiso 1 1 calc R U . . .
C25 C 0.2999(3) 0.9580(2) 0.0885(2) 0.0707(6) Uani 1 1 d . . . . .
H15 H 0.327568 1.033762 0.047581 0.085 Uiso 1 1 calc R U . . .
C26 C 0.43939(19) 0.65425(16) 0.17493(12) 0.0343(3) Uani 1 1 d . . . . .


_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 C19 1.685(2) . ?
S1 C18 1.7943(15) . ?
O1 C10 1.219(2) . ?
O2 C17 1.2221(18) . ?
N2 C19 1.137(3) . ?
C1 C25 1.356(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H4 0.9300 . ?
C4 C24 1.380(2) . ?
C4 C26 1.491(2) . ?
C5 C12 1.512(2) . ?
C5 C15 1.530(2) . ?
C5 C26 1.532(2) . ?
C5 C6 1.535(2) . ?
C6 C7 1.388(2) . ?
C6 C14 1.395(2) . ?
C7 C8 1.396(3) . ?
C7 C10 1.489(3) . ?
C8 C9 1.366(4) . ?
C8 H7 0.9300 . ?
C9 C13 1.377(3) . ?
C9 H2 0.9300 . ?
C10 C11 1.450(3) . ?
C11 C12 1.323(2) . ?
C11 H5 0.9300 . ?
C12 H6 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H9 0.9300 . ?
C14 H8 0.9300 . ?
C15 C16 1.391(2) . ?
C15 C23 1.395(2) . ?
C16 C20 1.408(2) . ?
C16 C17 1.469(2) . ?
C17 C18 1.478(2) . ?
C18 C26 1.343(2) . ?
C20 C21 1.375(3) . ?
C20 H13 0.9300 . ?
C21 C22 1.379(3) . ?
C21 H12 0.9300 . ?
C22 C23 1.377(2) . ?
C22 H10 0.9300 . ?
C23 H11 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H14 0.9300 . ?
C25 H15 0.9300 . ?

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
C19 S1 C18 96.65(8) . . ?
C25 C1 C2 119.84(18) . . ?
C25 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.01(18) . . ?
C3 C2 H3 120.0 . . ?
C1 C2 H3 120.0 . . ?
C2 C3 C4 121.07(18) . . ?
C2 C3 H4 119.5 . . ?
C4 C3 H4 119.5 . . ?
C24 C4 C3 118.28(15) . . ?
C24 C4 C26 120.95(14) . . ?
C3 C4 C26 120.78(15) . . ?
C12 C5 C15 105.98(12) . . ?
C12 C5 C26 108.56(12) . . ?
C15 C5 C26 114.02(12) . . ?
C12 C5 C6 112.82(13) . . ?
C15 C5 C6 108.29(12) . . ?
C26 C5 C6 107.30(12) . . ?
C7 C6 C14 119.38(16) . . ?
C7 C6 C5 121.72(15) . . ?
C14 C6 C5 118.86(14) . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 C10 120.76(16) . . ?
C8 C7 C10 119.96(18) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H7 119.5 . . ?
C7 C8 H7 119.5 . . ?
C8 C9 C13 120.1(2) . . ?
C8 C9 H2 119.9 . . ?
C13 C9 H2 119.9 . . ?
O1 C10 C11 121.4(2) . . ?
O1 C10 C7 121.0(2) . . ?
C11 C10 C7 117.55(15) . . ?
C12 C11 C10 122.70(18) . . ?
C12 C11 H5 118.7 . . ?
C10 C11 H5 118.7 . . ?
C11 C12 C5 124.21(16) . . ?
C11 C12 H6 117.9 . . ?
C5 C12 H6 117.9 . . ?
C9 C13 C14 120.0(2) . . ?
C9 C13 H9 120.0 . . ?
C14 C13 H9 120.0 . . ?
C13 C14 C6 120.28(18) . . ?
C13 C14 H8 119.9 . . ?
C6 C14 H8 119.9 . . ?
C16 C15 C23 118.78(14) . . ?
C16 C15 C5 122.55(13) . . ?
C23 C15 C5 118.63(14) . . ?
C15 C16 C20 119.94(15) . . ?
C15 C16 C17 120.69(13) . . ?
C20 C16 C17 119.37(15) . . ?
O2 C17 C16 122.15(14) . . ?
O2 C17 C18 120.70(15) . . ?
C16 C17 C18 117.14(13) . . ?
C26 C18 C17 124.24(14) . . ?
C26 C18 S1 120.09(11) . . ?
C17 C18 S1 115.52(11) . . ?
N2 C19 S1 178.68(19) . . ?
C21 C20 C16 119.96(17) . . ?
C21 C20 H13 120.0 . . ?
C16 C20 H13 120.0 . . ?
C20 C21 C22 120.15(15) . . ?
C20 C21 H12 119.9 . . ?
C22 C21 H12 119.9 . . ?
C23 C22 C21 120.34(17) . . ?
C23 C22 H10 119.8 . . ?
C21 C22 H10 119.8 . . ?
C22 C23 C15 120.83(17) . . ?
C22 C23 H11 119.6 . . ?
C15 C23 H11 119.6 . . ?
C4 C24 C25 120.22(18) . . ?
C4 C24 H14 119.9 . . ?
C25 C24 H14 119.9 . . ?
C1 C25 C24 120.5(2) . . ?
C1 C25 H15 119.7 . . ?
C24 C25 H15 119.7 . . ?
C18 C26 C4 122.79(14) . . ?
C18 C26 C5 120.94(13) . . ?
C4 C26 C5 116.27(12) . . ?

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
C25 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C24 -1.0(3) . . . . ?
C2 C3 C4 C26 178.82(16) . . . . ?
C12 C5 C6 C7 -5.0(2) . . . . ?
C15 C5 C6 C7 111.97(17) . . . . ?
C26 C5 C6 C7 -124.53(16) . . . . ?
C12 C5 C6 C14 177.22(13) . . . . ?
C15 C5 C6 C14 -65.80(18) . . . . ?
C26 C5 C6 C14 57.70(17) . . . . ?
C14 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 -177.51(18) . . . . ?
C14 C6 C7 C10 179.59(16) . . . . ?
C5 C6 C7 C10 1.8(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C10 C7 C8 C9 179.5(2) . . . . ?
C7 C8 C9 C13 0.7(4) . . . . ?
C6 C7 C10 O1 -178.23(19) . . . . ?
C8 C7 C10 O1 1.1(3) . . . . ?
C6 C7 C10 C11 2.0(3) . . . . ?
C8 C7 C10 C11 -178.6(2) . . . . ?
O1 C10 C11 C12 177.9(2) . . . . ?
C7 C10 C11 C12 -2.3(3) . . . . ?
C10 C11 C12 C5 -1.4(3) . . . . ?
C15 C5 C12 C11 -113.45(18) . . . . ?
C26 C5 C12 C11 123.68(17) . . . . ?
C6 C5 C12 C11 4.9(2) . . . . ?
C8 C9 C13 C14 0.7(4) . . . . ?
C9 C13 C14 C6 -1.7(3) . . . . ?
C7 C6 C14 C13 1.2(3) . . . . ?
C5 C6 C14 C13 178.99(16) . . . . ?
C12 C5 C15 C16 -113.96(16) . . . . ?
C26 C5 C15 C16 5.4(2) . . . . ?
C6 C5 C15 C16 124.74(16) . . . . ?
C12 C5 C15 C23 63.77(18) . . . . ?
C26 C5 C15 C23 -176.89(13) . . . . ?
C6 C5 C15 C23 -57.53(19) . . . . ?
C23 C15 C16 C20 0.0(2) . . . . ?
C5 C15 C16 C20 177.73(15) . . . . ?
C23 C15 C16 C17 179.82(15) . . . . ?
C5 C15 C16 C17 -2.5(2) . . . . ?
C15 C16 C17 O2 175.78(16) . . . . ?
C20 C16 C17 O2 -4.4(2) . . . . ?
C15 C16 C17 C18 -3.5(2) . . . . ?
C20 C16 C17 C18 176.32(14) . . . . ?
O2 C17 C18 C26 -172.51(16) . . . . ?
C16 C17 C18 C26 6.8(2) . . . . ?
O2 C17 C18 S1 3.0(2) . . . . ?
C16 C17 C18 S1 -177.73(11) . . . . ?
C19 S1 C18 C26 -112.84(14) . . . . ?
C19 S1 C18 C17 71.47(13) . . . . ?
C15 C16 C20 C21 -0.1(3) . . . . ?
C17 C16 C20 C21 -179.93(15) . . . . ?
C16 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C15 -0.5(3) . . . . ?
C16 C15 C23 C22 0.3(3) . . . . ?
C5 C15 C23 C22 -177.53(16) . . . . ?
C3 C4 C24 C25 2.1(3) . . . . ?
C26 C4 C24 C25 -177.73(18) . . . . ?
C2 C1 C25 C24 -0.3(3) . . . . ?
C4 C24 C25 C1 -1.5(3) . . . . ?
C17 C18 C26 C4 176.67(14) . . . . ?
S1 C18 C26 C4 1.4(2) . . . . ?
C17 C18 C26 C5 -3.7(2) . . . . ?
S1 C18 C26 C5 -178.97(10) . . . . ?
C24 C4 C26 C18 -102.5(2) . . . . ?
C3 C4 C26 C18 77.7(2) . . . . ?
C24 C4 C26 C5 77.87(19) . . . . ?
C3 C4 C26 C5 -101.99(18) . . . . ?
C12 C5 C26 C18 115.56(15) . . . . ?
C15 C5 C26 C18 -2.3(2) . . . . ?
C6 C5 C26 C18 -122.23(15) . . . . ?
C12 C5 C26 C4 -64.77(16) . . . . ?
C15 C5 C26 C4 177.36(12) . . . . ?
C6 C5 C26 C4 57.44(16) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.047

