# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_BNTD
_database_code_depnum_ccdc_archive 'CCDC 2350924'
loop_
_audit_author_name
_audit_author_address
'Diane A. Dickie'
;University of Virginia
United States of America
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BNTD
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         266.30

_chemical_melting_point          ?

_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                   7.6112(4)
_cell_length_b                   8.5345(5)
_cell_length_c                   9.9571(6)
_cell_angle_alpha                111.229(2)
_cell_angle_beta                 102.154(2)
_cell_angle_gamma                93.290(2)
_cell_volume                     583.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7590
_cell_measurement_theta_min      2.2656
_cell_measurement_theta_max      27.4683
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.081
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276

_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'

_diffrn_measurement_device       'Kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            16732
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2657
_reflns_number_gt                2350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1089
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_number_reflns         2657
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.4148P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker Instrument Service v8.5.0.27'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.09697(6) 0.73223(5) 0.31613(5) 0.01980(14) Uani d . . . 1 . .
O O1 -0.06620(17) 0.80604(16) 0.33438(15) 0.0277(3) Uani d . . . 1 . .
O O2 0.19326(18) 0.77703(16) 0.22180(14) 0.0256(3) Uani d . . . 1 . .
C C1 0.0558(2) 0.5118(2) 0.26640(19) 0.0187(3) Uani d . . . 1 . .
C C2 -0.0539(2) 0.3986(2) 0.13312(19) 0.0206(3) Uani d . . . 1 . .
H H2 -0.113628 0.436511 0.059174 0.025000 Uiso calc U . R 1 . .
C C3 -0.0742(2) 0.2273(2) 0.11043(19) 0.0225(4) Uani d . . . 1 . .
H H3 -0.146329 0.145521 0.019001 0.027000 Uiso calc U . R 1 . .
C C4 0.0113(2) 0.1764(2) 0.2221(2) 0.0229(4) Uani d . . . 1 . .
H H4 -0.005582 0.059503 0.206734 0.027000 Uiso calc U . R 1 . .
C C5 0.1212(2) 0.2925(2) 0.35594(19) 0.0210(3) Uani d . . . 1 . .
H H5 0.178124 0.254467 0.430659 0.025000 Uiso calc U . R 1 . .
C C6 0.1478(2) 0.4651(2) 0.38056(18) 0.0178(3) Uani d . . . 1 . .
C C7 0.2593(2) 0.6143(2) 0.50978(18) 0.0173(3) Uani d . . . 1 . .
C C8 0.3753(2) 0.6235(2) 0.64670(18) 0.0185(3) Uani d . . . 1 . .
C C9 0.4067(2) 0.4817(2) 0.68590(19) 0.0219(3) Uani d . . . 1 . .
H H9 0.349332 0.371295 0.617990 0.026000 Uiso calc U . R 1 . .
C C10 0.5186(2) 0.5009(2) 0.8202(2) 0.0250(4) Uani d . . . 1 . .
H H10 0.537733 0.403798 0.843580 0.030000 Uiso calc U . R 1 . .
C C11 0.6049(2) 0.6622(3) 0.9233(2) 0.0262(4) Uani d . . . 1 . .
H H11 0.681039 0.674081 1.016273 0.031000 Uiso calc U . R 1 . .
C C12 0.5792(2) 0.8017(2) 0.8894(2) 0.0245(4) Uani d . . . 1 . .
H H12 0.638113 0.910602 0.959572 0.029000 Uiso calc U . R 1 . .
C C13 0.4661(2) 0.7873(2) 0.75148(19) 0.0208(3) Uani d . . . 1 . .
C C14 0.4447(2) 0.9346(2) 0.7188(2) 0.0233(4) Uani d . . . 1 . .
H H14 0.507914 1.041696 0.789281 0.028000 Uiso calc U . R 1 . .
C C15 0.3353(2) 0.9253(2) 0.5884(2) 0.0225(4) Uani d . . . 1 . .
H H15 0.321097 1.023785 0.566135 0.027000 Uiso calc U . R 1 . .
C C16 0.2444(2) 0.7647(2) 0.48814(18) 0.0188(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4402(13) ?
S1 O2 . 1.4434(13) ?
S1 C1 . 1.7539(17) ?
S1 C16 . 1.7550(17) ?
C1 C2 . 1.380(2) ?
C1 C6 . 1.402(2) ?
C2 C3 . 1.390(2) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.392(2) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.397(2) ?
C5 H5 . 0.950000 ?
C6 C7 . 1.492(2) ?
C7 C16 . 1.384(2) ?
C7 C8 . 1.432(2) ?
C8 C9 . 1.418(2) ?
C8 C13 . 1.431(2) ?
C9 C10 . 1.373(2) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.403(3) ?
C10 H10 . 0.950000 ?
C11 C12 . 1.364(3) ?
C11 H11 . 0.950000 ?
C12 C13 . 1.418(2) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.418(2) ?
C14 C15 . 1.359(3) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.401(2) ?
C15 H15 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 116.38(8) ?
O1 S1 C1 . . 110.63(8) ?
O2 S1 C1 . . 112.16(8) ?
O1 S1 C16 . . 111.64(8) ?
O2 S1 C16 . . 110.85(8) ?
C1 S1 C16 . . 92.77(8) ?
C2 C1 C6 . . 124.17(16) ?
C2 C1 S1 . . 124.68(13) ?
C6 C1 S1 . . 111.15(12) ?
C1 C2 C3 . . 117.93(16) ?
C1 C2 H2 . . 121.000000 ?
C3 C2 H2 . . 121.000000 ?
C4 C3 C2 . . 119.63(16) ?
C4 C3 H3 . . 120.200000 ?
C2 C3 H3 . . 120.200000 ?
C3 C4 C5 . . 121.61(16) ?
C3 C4 H4 . . 119.200000 ?
C5 C4 H4 . . 119.200000 ?
C4 C5 C6 . . 120.06(16) ?
C4 C5 H5 . . 120.000000 ?
C6 C5 H5 . . 120.000000 ?
C5 C6 C1 . . 116.56(15) ?
C5 C6 C7 . . 131.35(15) ?
C1 C6 C7 . . 112.08(14) ?
C16 C7 C8 . . 117.40(15) ?
C16 C7 C6 . . 112.10(14) ?
C8 C7 C6 . . 130.50(15) ?
C9 C8 C13 . . 117.57(15) ?
C9 C8 C7 . . 124.58(15) ?
C13 C8 C7 . . 117.84(15) ?
C10 C9 C8 . . 121.21(17) ?
C10 C9 H9 . . 119.400000 ?
C8 C9 H9 . . 119.400000 ?
C9 C10 C11 . . 120.89(17) ?
C9 C10 H10 . . 119.600000 ?
C11 C10 H10 . . 119.600000 ?
C12 C11 C10 . . 119.72(17) ?
C12 C11 H11 . . 120.100000 ?
C10 C11 H11 . . 120.100000 ?
C11 C12 C13 . . 121.20(17) ?
C11 C12 H12 . . 119.400000 ?
C13 C12 H12 . . 119.400000 ?
C12 C13 C14 . . 119.77(16) ?
C12 C13 C8 . . 119.40(16) ?
C14 C13 C8 . . 120.84(16) ?
C15 C14 C13 . . 121.19(16) ?
C15 C14 H14 . . 119.400000 ?
C13 C14 H14 . . 119.400000 ?
C14 C15 C16 . . 117.36(16) ?
C14 C15 H15 . . 121.300000 ?
C16 C15 H15 . . 121.300000 ?
C7 C16 C15 . . 125.35(16) ?
C7 C16 S1 . . 111.85(12) ?
C15 C16 S1 . . 122.80(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . 66.97(16) ?
O2 S1 C1 C2 . . . . -64.78(17) ?
C16 S1 C1 C2 . . . . -178.65(15) ?
O1 S1 C1 C6 . . . . -112.46(13) ?
O2 S1 C1 C6 . . . . 115.78(12) ?
C16 S1 C1 C6 . . . . 1.92(13) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
S1 C1 C2 C3 . . . . -179.51(12) ?
C1 C2 C3 C4 . . . . 1.6(2) ?
C2 C3 C4 C5 . . . . -1.5(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C4 C5 C6 C1 . . . . 1.4(2) ?
C4 C5 C6 C7 . . . . -178.59(16) ?
C2 C1 C6 C5 . . . . -1.4(2) ?
S1 C1 C6 C5 . . . . 178.09(12) ?
C2 C1 C6 C7 . . . . 178.66(15) ?
S1 C1 C6 C7 . . . . -1.90(17) ?
C5 C6 C7 C16 . . . . -179.13(16) ?
C1 C6 C7 C16 . . . . 0.86(19) ?
C5 C6 C7 C8 . . . . 1.2(3) ?
C1 C6 C7 C8 . . . . -178.82(16) ?
C16 C7 C8 C9 . . . . -179.51(15) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C16 C7 C8 C13 . . . . 0.4(2) ?
C6 C7 C8 C13 . . . . -179.92(15) ?
C13 C8 C9 C10 . . . . 0.7(2) ?
C7 C8 C9 C10 . . . . -179.34(15) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . -178.95(16) ?
C11 C12 C13 C8 . . . . 0.9(3) ?
C9 C8 C13 C12 . . . . -1.3(2) ?
C7 C8 C13 C12 . . . . 178.78(15) ?
C9 C8 C13 C14 . . . . 178.56(15) ?
C7 C8 C13 C14 . . . . -1.4(2) ?
C12 C13 C14 C15 . . . . -179.09(16) ?
C8 C13 C14 C15 . . . . 1.1(3) ?
C13 C14 C15 C16 . . . . 0.2(2) ?
C8 C7 C16 C15 . . . . 0.9(2) ?
C6 C7 C16 C15 . . . . -178.81(15) ?
C8 C7 C16 S1 . . . . -179.68(11) ?
C6 C7 C16 S1 . . . . 0.59(17) ?
C14 C15 C16 C7 . . . . -1.2(3) ?
C14 C15 C16 S1 . . . . 179.41(13) ?
O1 S1 C16 C7 . . . . 112.06(13) ?
O2 S1 C16 C7 . . . . -116.43(12) ?
C1 S1 C16 C7 . . . . -1.43(13) ?
O1 S1 C16 C15 . . . . -68.51(16) ?
O2 S1 C16 C15 . . . . 62.99(16) ?
C1 S1 C16 C15 . . . . 177.99(14) ?



