# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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 
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data_3BTHMB
_database_code_depnum_ccdc_archive 'CCDC 2250779'
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        3BTHMB
_chemical_name_common            3BTHMB
_chemical_melting_point          463
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O3 S'
_chemical_formula_weight         285.31

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   27.449(6)
_cell_length_b                   5.9185(12)
_cell_length_c                   7.8408(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1273.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9414
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      33.2

_exptl_crystal_description       rhombic
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26134
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.442
_diffrn_reflns_theta_max         33.885
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4928
_reflns_number_gt                4581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.995

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0499P)²+0.2226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4928
_refine_ls_number_parameters     187
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

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 0.75867(2) 1.02859(7) 0.61945(7) 0.03463(11) Uani 1 1 d . . . . .
O2 O 0.58511(5) 0.3939(2) 0.3528(2) 0.0420(3) Uani 1 1 d . . . . .
O1 O 0.52325(6) 1.1066(3) 0.6844(3) 0.0596(5) Uani 1 1 d . . . . .
O3 O 0.67933(5) 0.4203(2) 0.3776(2) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.75761(5) 0.6378(3) 0.4711(2) 0.0312(3) Uani 1 1 d . . . . .
C11 C 0.89214(7) 0.6418(4) 0.4729(3) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.918831 0.555524 0.439749 0.055 Uiso 1 1 calc R U . . .
C10 C 0.84574(7) 0.5615(4) 0.4414(3) 0.0398(4) Uani 1 1 d . . . . .
H9 H 0.840968 0.422958 0.388033 0.048 Uiso 1 1 calc R U . . .
C15 C 0.80622(6) 0.6940(3) 0.4919(2) 0.0312(3) Uani 1 1 d . . . . .
C9 C 0.72893(6) 0.7945(3) 0.5326(2) 0.0291(3) Uani 1 1 d . . . . .
C4 C 0.67598(6) 0.7781(3) 0.5261(2) 0.0284(3) Uani 1 1 d . . . . .
C5 C 0.65392(6) 0.5903(3) 0.4469(2) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.60228(6) 0.5782(3) 0.4362(2) 0.0317(3) Uani 1 1 d . . . . .
C8 C 0.53412(7) 0.3877(4) 0.3162(4) 0.0505(5) Uani 1 1 d . . . . .
H6 H 0.516116 0.381045 0.421054 0.076 Uiso 1 1 calc R U . . .
H5 H 0.526909 0.256610 0.248644 0.076 Uiso 1 1 calc R U . . .
H7 H 0.525082 0.521244 0.254349 0.076 Uiso 1 1 calc R U . . .
C12 C 0.89991(7) 0.8483(4) 0.5529(3) 0.0446(4) Uani 1 1 d . . . . .
H11 H 0.931648 0.896986 0.572234 0.053 Uiso 1 1 calc R U . . .
C13 C 0.86121(6) 0.9837(3) 0.6046(3) 0.0397(4) Uani 1 1 d . . . . .
H12 H 0.866395 1.121383 0.658751 0.048 Uiso 1 1 calc R U . . .
C14 C 0.81411(6) 0.9038(3) 0.5717(2) 0.0319(3) Uani 1 1 d . . . . .
C3 C 0.64642(6) 0.9465(3) 0.5974(2) 0.0332(3) Uani 1 1 d . . . . .
H2 H 0.660682 1.070784 0.650070 0.040 Uiso 1 1 calc R U . . .
C2 C 0.59628(6) 0.9294(3) 0.5902(2) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.56709(8) 1.1048(4) 0.6734(3) 0.0442(4) Uani 1 1 d . . . . .
H1 H 0.583817 1.225296 0.721969 0.053 Uiso 1 1 calc R U . . .
C7 C 0.57408(6) 0.7458(3) 0.5082(3) 0.0347(3) Uani 1 1 d . . . . .
H3 H 0.540294 0.736997 0.502417 0.042 Uiso 1 1 calc R U . . .
H8 H 0.7093(12) 0.451(5) 0.387(5) 0.056(8) Uiso 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 C14 1.7325(18) . ?
S1 C9 1.7463(17) . ?
O2 C6 1.356(2) . ?
O2 C8 1.429(2) . ?
O1 C1 1.207(3) . ?
O3 C5 1.340(2) . ?
O3 H8 0.85(3) . ?
N1 C9 1.309(2) . ?
N1 C15 1.385(2) . ?
C11 C10 1.382(3) . ?
C11 C12 1.390(3) . ?
C11 H10 0.9300 . ?
C10 C15 1.396(2) . ?
C10 H9 0.9300 . ?
C15 C14 1.407(3) . ?
C9 C4 1.458(2) . ?
C4 C3 1.402(2) . ?
C4 C5 1.410(2) . ?
C5 C6 1.422(2) . ?
C6 C7 1.379(2) . ?
C8 H6 0.9600 . ?
C8 H5 0.9600 . ?
C8 H7 0.9600 . ?
C12 C13 1.391(3) . ?
C12 H11 0.9300 . ?
C13 C14 1.401(2) . ?
C13 H12 0.9300 . ?
C3 C2 1.381(2) . ?
C3 H2 0.9300 . ?
C2 C7 1.402(3) . ?
C2 C1 1.464(3) . ?
C1 H1 0.9300 . ?
C7 H3 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
C14 S1 C9 89.31(8) . . ?
C6 O2 C8 117.24(16) . . ?
C5 O3 H8 108(2) . . ?
C9 N1 C15 111.47(15) . . ?
C10 C11 C12 121.62(19) . . ?
C10 C11 H10 119.2 . . ?
C12 C11 H10 119.2 . . ?
C11 C10 C15 118.22(19) . . ?
C11 C10 H9 120.9 . . ?
C15 C10 H9 120.9 . . ?
N1 C15 C10 125.50(17) . . ?
N1 C15 C14 114.37(15) . . ?
C10 C15 C14 120.13(16) . . ?
N1 C9 C4 122.66(14) . . ?
N1 C9 S1 115.14(12) . . ?
C4 C9 S1 122.18(12) . . ?
C3 C4 C5 119.18(14) . . ?
C3 C4 C9 121.05(14) . . ?
C5 C4 C9 119.76(14) . . ?
O3 C5 C4 123.18(14) . . ?
O3 C5 C6 117.20(15) . . ?
C4 C5 C6 119.62(15) . . ?
O2 C6 C7 125.51(15) . . ?
O2 C6 C5 114.56(15) . . ?
C7 C6 C5 119.93(16) . . ?
O2 C8 H6 109.5 . . ?
O2 C8 H5 109.5 . . ?
H6 C8 H5 109.5 . . ?
O2 C8 H7 109.5 . . ?
H6 C8 H7 109.5 . . ?
H5 C8 H7 109.5 . . ?
C13 C12 C11 121.38(18) . . ?
C13 C12 H11 119.3 . . ?
C11 C12 H11 119.3 . . ?
C12 C13 C14 117.19(19) . . ?
C12 C13 H12 121.4 . . ?
C14 C13 H12 121.4 . . ?
C13 C14 C15 121.45(17) . . ?
C13 C14 S1 128.84(15) . . ?
C15 C14 S1 109.70(12) . . ?
C2 C3 C4 120.56(15) . . ?
C2 C3 H2 119.7 . . ?
C4 C3 H2 119.7 . . ?
C3 C2 C7 120.58(15) . . ?
C3 C2 C1 118.36(17) . . ?
C7 C2 C1 121.04(16) . . ?
O1 C1 C2 125.7(2) . . ?
O1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C6 C7 C2 120.08(15) . . ?
C6 C7 H3 120.0 . . ?
C2 C7 H3 120.0 . . ?

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
C12 C11 C10 C15 0.1(3) . . . . ?
C9 N1 C15 C10 179.33(18) . . . . ?
C9 N1 C15 C14 -0.5(2) . . . . ?
C11 C10 C15 N1 -179.50(19) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C15 N1 C9 C4 179.58(15) . . . . ?
C15 N1 C9 S1 0.92(19) . . . . ?
C14 S1 C9 N1 -0.84(14) . . . . ?
C14 S1 C9 C4 -179.51(14) . . . . ?
N1 C9 C4 C3 178.29(16) . . . . ?
S1 C9 C4 C3 -3.1(2) . . . . ?
N1 C9 C4 C5 -1.7(2) . . . . ?
S1 C9 C4 C5 176.84(12) . . . . ?
C3 C4 C5 O3 -179.06(16) . . . . ?
C9 C4 C5 O3 1.0(2) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C9 C4 C5 C6 -178.10(15) . . . . ?
C8 O2 C6 C7 9.0(3) . . . . ?
C8 O2 C6 C5 -171.27(18) . . . . ?
O3 C5 C6 O2 -1.1(2) . . . . ?
C4 C5 C6 O2 178.03(15) . . . . ?
O3 C5 C6 C7 178.66(17) . . . . ?
C4 C5 C6 C7 -2.2(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C12 C13 C14 S1 179.79(16) . . . . ?
N1 C15 C14 C13 178.99(17) . . . . ?
C10 C15 C14 C13 -0.9(3) . . . . ?
N1 C15 C14 S1 -0.11(18) . . . . ?
C10 C15 C14 S1 -179.97(15) . . . . ?
C9 S1 C14 C13 -178.51(18) . . . . ?
C9 S1 C14 C15 0.49(13) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C9 C4 C3 C2 179.87(16) . . . . ?
C4 C3 C2 C7 -1.4(3) . . . . ?
C4 C3 C2 C1 177.29(17) . . . . ?
C3 C2 C1 O1 -176.3(2) . . . . ?
C7 C2 C1 O1 2.3(3) . . . . ?
O2 C6 C7 C2 -179.51(18) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C1 C2 C7 C6 -177.59(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H8 N1 0.85(3) 1.85(3) 2.610(2) 149(3) .
C13 H12 O2 0.93 2.59 3.443(3) 153.4 3_665
C8 H7 O1 0.96 2.63 3.536(3) 157.8 2_674
C8 H5 O1 0.96 2.60 3.479(3) 152.1 2_664
C8 H6 O1 0.96 2.63 3.345(4) 131.2 1_545
O3 H8 N1 0.85(3) 1.85(3) 2.610(2) 149(3) .
C13 H12 O2 0.93 2.59 3.443(3) 153.4 3_665
C8 H7 O1 0.96 2.63 3.536(3) 157.8 2_674
C8 H5 O1 0.96 2.60 3.479(3) 152.1 2_664
C8 H6 O1 0.96 2.63 3.345(4) 131.2 1_545
O3 H8 N1 0.85(3) 1.85(3) 2.610(2) 149(3) .
O3 H8 N1 0.85(3) 1.85(3) 2.610(2) 149(3) .

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062

