# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_MKB_INDOLE_QUINO_THIO18_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2449281'
_audit_update_record             
;
2025-05-07 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N2 S2'
_chemical_formula_weight         408.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.6925(19)
_cell_length_b                   15.819(2)
_cell_length_c                   10.5522(16)
_cell_angle_alpha                90
_cell_angle_beta                 112.458(5)
_cell_angle_gamma                90
_cell_volume                     1958.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    45337
_cell_measurement_theta_min      1.735
_cell_measurement_theta_max      24.895

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44247
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_max         23.511
_diffrn_reflns_theta_full        23.511
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2887
_reflns_number_gt                2248
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1126P)²+7.0915P] 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         2887
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2479
_refine_ls_wR_factor_gt          0.2232
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.8410(2) 0.61315(15) 1.0143(2) 0.0964(9) Uani 1 1 d . . . . .
S2 S 0.90328(13) 0.49751(10) 0.74031(16) 0.0499(5) Uani 1 1 d . . . . .
N1 N 0.6351(4) 0.4598(3) 0.9524(5) 0.0473(12) Uani 1 1 d . . . . .
N2 N 0.7376(4) 0.3252(3) 0.8684(4) 0.0375(11) Uani 1 1 d . . . . .
C1 C 0.6590(4) 0.3070(3) 0.9294(5) 0.0363(12) Uani 1 1 d . . . . .
C2 C 0.6296(5) 0.2255(4) 0.9533(6) 0.0458(14) Uani 1 1 d . . . . .
H2 H 0.662351 0.179051 0.928498 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5515(5) 0.2139(4) 1.0141(6) 0.0494(15) Uani 1 1 d . . . . .
H3 H 0.532632 0.159124 1.029757 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5016(5) 0.2803(4) 1.0517(7) 0.0546(16) Uani 1 1 d . . . . .
H4 H 0.448887 0.271088 1.091867 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5301(5) 0.3612(4) 1.0293(6) 0.0515(15) Uani 1 1 d . . . . .
H5 H 0.496553 0.406841 1.055063 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6088(5) 0.3759(3) 0.9684(6) 0.0405(13) Uani 1 1 d . . . . .
C7 C 0.7089(5) 0.4749(3) 0.8973(6) 0.0417(13) Uani 1 1 d . . . . .
C8 C 0.7635(4) 0.4096(3) 0.8504(5) 0.0354(12) Uani 1 1 d . . . . .
C9 C 0.8396(4) 0.4103(3) 0.7859(6) 0.0411(13) Uani 1 1 d . . . . .
C10 C 0.8624(4) 0.3251(3) 0.7633(5) 0.0390(13) Uani 1 1 d . . . . .
C11 C 0.7994(4) 0.2731(3) 0.8162(5) 0.0361(12) Uani 1 1 d . . . . .
C12 C 0.9309(5) 0.2892(4) 0.7004(6) 0.0489(15) Uani 1 1 d . . . . .
H12 H 0.972442 0.323465 0.664720 0.059 Uiso 1 1 calc R U . . .
C13 C 0.9360(5) 0.2031(4) 0.6922(6) 0.0541(16) Uani 1 1 d . . . . .
H13 H 0.982122 0.178728 0.651757 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8730(5) 0.1518(4) 0.7436(6) 0.0522(15) Uani 1 1 d . . . . .
H14 H 0.877178 0.093442 0.735820 0.063 Uiso 1 1 calc R U . . .
C15 C 0.8046(5) 0.1847(4) 0.8057(6) 0.0452(14) Uani 1 1 d . . . . .
H15 H 0.763000 0.149482 0.839846 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7373(5) 0.5657(3) 0.8871(6) 0.0457(14) Uani 1 1 d . . . . .
C17 C 0.7365(6) 0.7045(4) 0.8129(8) 0.071(2) Uani 1 1 d . . . . .
H17 H 0.717051 0.752332 0.757447 0.085 Uiso 1 1 calc R U . . .
C18 C 0.8201(7) 0.7051(5) 0.9342(8) 0.073(2) Uiso 1 1 d . . . . .
H18 H 0.863455 0.752957 0.971551 0.088 Uiso 1 1 calc R U . . .
C19 C 0.8148(5) 0.5135(3) 0.5656(6) 0.0419(13) Uani 1 1 d . . . . .
C20 C 0.7005(5) 0.4938(4) 0.5102(7) 0.0543(16) Uani 1 1 d . . . . .
H20 H 0.665668 0.470018 0.564964 0.065 Uiso 1 1 calc R U . . .
C21 C 0.6372(6) 0.5096(5) 0.3721(7) 0.071(2) Uani 1 1 d . . . . .
H21 H 0.560009 0.496143 0.334912 0.085 Uiso 1 1 calc R U . . .
C22 C 0.6871(8) 0.5446(5) 0.2907(7) 0.076(2) Uani 1 1 d . . . . .
H22 H 0.644553 0.554125 0.198128 0.091 Uiso 1 1 calc R U . . .
C23 C 0.7996(7) 0.5654(4) 0.3461(7) 0.069(2) Uani 1 1 d . . . . .
H23 H 0.833567 0.590016 0.291137 0.083 Uiso 1 1 calc R U . . .
C24 C 0.8635(6) 0.5507(4) 0.4818(7) 0.0548(16) Uani 1 1 d . . . . .
H24 H 0.940142 0.565740 0.518121 0.066 Uiso 1 1 calc R U . . .
C25 C 0.6746(4) 0.6228(3) 0.7692(5) 0.0293(11) Uiso 1 1 d . . . . .
H25 H 0.612589 0.610471 0.689014 0.035 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 C18 1.653(8) . ?
S1 C16 1.658(6) . ?
S2 C9 1.757(5) . ?
S2 C19 1.773(6) . ?
N1 C7 1.299(7) . ?
N1 C6 1.395(7) . ?
N2 C11 1.388(6) . ?
N2 C8 1.406(7) . ?
N2 C1 1.407(6) . ?
C1 C2 1.392(8) . ?
C1 C6 1.402(7) . ?
C2 C3 1.383(8) . ?
C3 C4 1.363(9) . ?
C4 C5 1.375(9) . ?
C5 C6 1.398(8) . ?
C7 C8 1.433(8) . ?
C7 C16 1.495(8) . ?
C8 C9 1.378(7) . ?
C9 C10 1.418(8) . ?
C10 C12 1.399(8) . ?
C10 C11 1.404(7) . ?
C11 C15 1.407(8) . ?
C12 C13 1.368(9) . ?
C13 C14 1.387(9) . ?
C14 C15 1.374(8) . ?
C16 C25 1.497(7) . ?
C17 C18 1.314(10) . ?
C17 C25 1.491(9) . ?
C19 C24 1.388(8) . ?
C19 C20 1.378(8) . ?
C20 C21 1.392(9) . ?
C21 C22 1.364(10) . ?
C22 C23 1.362(11) . ?
C23 C24 1.369(9) . ?

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
C18 S1 C16 93.5(4) . . ?
C9 S2 C19 102.8(3) . . ?
C7 N1 C6 118.4(5) . . ?
C11 N2 C8 108.3(4) . . ?
C11 N2 C1 131.8(4) . . ?
C8 N2 C1 119.9(4) . . ?
C2 C1 C6 118.9(5) . . ?
C2 C1 N2 123.9(5) . . ?
C6 C1 N2 117.2(5) . . ?
C1 C2 C3 119.8(5) . . ?
C4 C3 C2 121.8(6) . . ?
C3 C4 C5 119.1(5) . . ?
C4 C5 C6 121.0(6) . . ?
C1 C6 N1 123.2(5) . . ?
C1 C6 C5 119.4(5) . . ?
N1 C6 C5 117.4(5) . . ?
N1 C7 C8 123.3(5) . . ?
N1 C7 C16 116.3(5) . . ?
C8 C7 C16 120.4(5) . . ?
C9 C8 N2 108.6(4) . . ?
C9 C8 C7 133.4(5) . . ?
N2 C8 C7 118.0(5) . . ?
C8 C9 C10 107.6(5) . . ?
C8 C9 S2 128.6(4) . . ?
C10 C9 S2 123.7(4) . . ?
C12 C10 C11 120.2(5) . . ?
C12 C10 C9 132.1(5) . . ?
C11 C10 C9 107.8(5) . . ?
N2 C11 C10 107.7(4) . . ?
N2 C11 C15 132.2(5) . . ?
C10 C11 C15 120.0(5) . . ?
C13 C12 C10 119.1(5) . . ?
C14 C13 C12 120.7(6) . . ?
C13 C14 C15 121.9(6) . . ?
C14 C15 C11 118.2(5) . . ?
C25 C16 C7 125.0(5) . . ?
C25 C16 S1 113.9(4) . . ?
C7 C16 S1 121.0(4) . . ?
C18 C17 C25 116.2(6) . . ?
C17 C18 S1 113.8(6) . . ?
C24 C19 C20 118.6(6) . . ?
C24 C19 S2 117.6(5) . . ?
C20 C19 S2 123.7(5) . . ?
C19 C20 C21 119.8(6) . . ?
C22 C21 C20 120.8(7) . . ?
C23 C22 C21 119.4(7) . . ?
C22 C23 C24 120.9(7) . . ?
C23 C24 C19 120.6(6) . . ?
C17 C25 C16 102.5(5) . . ?

_refine_diff_density_max         0.892
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.082

