# Supplementary Information (SI) for Chemical Science.
# 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. 
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data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2431275'
loop_
_audit_author_name
_audit_author_address
'Javier Carreras'
;Universidad de Alcala
Spain
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O6 S'
_chemical_formula_sum            'C19 H18 N2 O6 S'
_chemical_formula_weight         402.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.2636(3)
_cell_length_b                   10.5834(4)
_cell_length_c                   12.5316(4)
_cell_angle_alpha                72.0730(10)
_cell_angle_beta                 74.0080(10)
_cell_angle_gamma                67.2850(10)
_cell_volume                     946.44(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      6.41
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.767
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1226 before and 0.0784 after correction. The Ratio of minimum to maximum transmission is 0.6993. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_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            25306
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.429
_diffrn_reflns_theta_min         6.412
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3167
_reflns_number_total             3656
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.3451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C17(H17), C15(H15), C4(H4), C7(H7), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.13061(5) 0.55226(5) 0.75696(4) 0.05135(18) Uani 1 1 d . . . . .
O1 O 0.57117(17) 0.34292(15) 0.51288(11) 0.0568(4) Uani 1 1 d . . . . .
O3 O 0.19437(19) 0.46829(17) 0.43362(11) 0.0608(4) Uani 1 1 d . . . . .
O2 O 0.2734(2) 0.13370(17) 0.83861(12) 0.0686(4) Uani 1 1 d . . . . .
N1 N 0.19002(19) 0.50416(16) 0.63696(13) 0.0439(3) Uani 1 1 d . . . . .
N2 N 0.38382(18) 0.26075(15) 0.66708(11) 0.0423(3) Uani 1 1 d . . . . .
O6 O -0.01310(18) 0.5030(2) 0.82185(13) 0.0722(5) Uani 1 1 d . . . . .
O4 O 0.2525(2) 0.23475(16) 0.50037(13) 0.0639(4) Uani 1 1 d . . . . .
O5 O 0.1063(2) 0.69902(16) 0.72551(16) 0.0763(5) Uani 1 1 d . . . . .
C10 C 0.2194(2) 0.3648(2) 0.50849(15) 0.0474(4) Uani 1 1 d . . . . .
C2 C 0.3975(3) 0.16042(18) 0.77149(15) 0.0482(4) Uani 1 1 d . . . . .
C1 C 0.5501(2) 0.26598(18) 0.60572(15) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.2179(2) 0.36359(19) 0.63185(14) 0.0424(4) Uani 1 1 d . . . . .
H9 H 0.117694 0.334718 0.681537 0.051 Uiso 1 1 calc R . . . .
C3 C 0.5912(3) 0.10020(19) 0.77523(17) 0.0522(4) Uani 1 1 d . . . . .
C13 C 0.3116(2) 0.46535(19) 0.83069(15) 0.0448(4) Uani 1 1 d . . . . .
C8 C 0.6821(2) 0.16274(19) 0.67636(18) 0.0511(4) Uani 1 1 d . . . . .
C18 C 0.2846(3) 0.3930(2) 0.94281(16) 0.0563(5) Uani 1 1 d . . . . .
H18 H 0.172483 0.387026 0.979239 0.068 Uiso 1 1 calc R . . . .
C14 C 0.4780(2) 0.4748(2) 0.77666(15) 0.0480(4) Uani 1 1 d . . . . .
H14 H 0.494655 0.525438 0.701662 0.058 Uiso 1 1 calc R . . . .
C16 C 0.5963(3) 0.3346(2) 0.94722(17) 0.0548(5) Uani 1 1 d . . . . .
C17 C 0.4274(3) 0.3295(2) 0.99990(17) 0.0624(5) Uani 1 1 d . . . . .
H17 H 0.409436 0.281977 1.075804 0.075 Uiso 1 1 calc R . . . .
C15 C 0.6196(3) 0.4087(2) 0.83474(17) 0.0535(5) Uani 1 1 d . . . . .
H15 H 0.731908 0.413860 0.797947 0.064 Uiso 1 1 calc R . . . .
C4 C 0.6810(4) 0.0009(2) 0.8594(2) 0.0752(7) Uani 1 1 d . . . . .
H4 H 0.620501 -0.041448 0.926377 0.090 Uiso 1 1 calc R . . . .
C7 C 0.8651(3) 0.1299(3) 0.6569(3) 0.0734(6) Uani 1 1 d . . . . .
H7 H 0.925728 0.172381 0.590176 0.088 Uiso 1 1 calc R . . . .
C12 C 0.4762(4) 0.1481(3) 0.3467(2) 0.0801(7) Uani 1 1 d . . . . .
H12A H 0.495969 0.130316 0.272660 0.120 Uiso 1 1 calc GR . . . .
H12B H 0.520634 0.061001 0.399673 0.120 Uiso 1 1 calc GR . . . .
H12C H 0.537306 0.210711 0.342609 0.120 Uiso 1 1 calc GR . . . .
C19 C 0.7522(4) 0.2598(3) 1.0089(2) 0.0775(7) Uani 1 1 d . . . . .
H19A H 0.730259 0.297648 1.073982 0.116 Uiso 1 1 calc GR . . . .
H19B H 0.858285 0.272991 0.958492 0.116 Uiso 1 1 calc GR . . . .
H19C H 0.767497 0.161242 1.033514 0.116 Uiso 1 1 calc GR . . . .
C5 C 0.8628(4) -0.0325(3) 0.8402(3) 0.0962(10) Uani 1 1 d . . . . .
H5 H 0.926615 -0.099510 0.895099 0.115 Uiso 1 1 calc R . . . .
C11 C 0.2836(4) 0.2127(3) 0.3851(2) 0.0842(8) Uani 1 1 d . . . . .
H11A H 0.238731 0.302121 0.332941 0.101 Uiso 1 1 calc R . . . .
H11B H 0.220525 0.151881 0.385626 0.101 Uiso 1 1 calc R . . . .
C6 C 0.9536(4) 0.0307(3) 0.7416(3) 0.0958(10) Uani 1 1 d . . . . .
H6 H 1.076717 0.006003 0.731879 0.115 Uiso 1 1 calc R . . . .
H1 H 0.250(3) 0.546(2) 0.5877(19) 0.052(6) 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 N1 1.6226(15) . ?
S1 O6 1.4242(16) . ?
S1 O5 1.4262(17) . ?
S1 C13 1.7640(18) . ?
O1 C1 1.209(2) . ?
O3 C10 1.193(2) . ?
O2 C2 1.200(2) . ?
N1 C9 1.434(2) . ?
N1 H1 0.81(2) . ?
N2 C2 1.409(2) . ?
N2 C1 1.390(2) . ?
N2 C9 1.465(2) . ?
O4 C10 1.326(2) . ?
O4 C11 1.471(3) . ?
C10 C9 1.539(2) . ?
C2 C3 1.485(3) . ?
C1 C8 1.477(2) . ?
C9 H9 0.9800 . ?
C3 C8 1.379(3) . ?
C3 C4 1.384(3) . ?
C13 C18 1.381(3) . ?
C13 C14 1.383(2) . ?
C8 C7 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C16 C17 1.384(3) . ?
C16 C15 1.387(3) . ?
C16 C19 1.506(3) . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.382(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C11 1.474(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6 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
N1 S1 C13 107.67(8) . . ?
O6 S1 N1 107.37(9) . . ?
O6 S1 O5 120.39(11) . . ?
O6 S1 C13 107.85(9) . . ?
O5 S1 N1 104.77(10) . . ?
O5 S1 C13 108.18(9) . . ?
S1 N1 H1 114.1(16) . . ?
C9 N1 S1 122.03(12) . . ?
C9 N1 H1 116.8(16) . . ?
C2 N2 C9 125.69(14) . . ?
C1 N2 C2 111.74(14) . . ?
C1 N2 C9 121.97(13) . . ?
C10 O4 C11 116.81(18) . . ?
O3 C10 O4 126.68(17) . . ?
O3 C10 C9 123.98(18) . . ?
O4 C10 C9 109.34(16) . . ?
O2 C2 N2 124.60(18) . . ?
O2 C2 C3 130.40(18) . . ?
N2 C2 C3 104.99(15) . . ?
O1 C1 N2 123.38(16) . . ?
O1 C1 C8 130.26(17) . . ?
N2 C1 C8 106.36(15) . . ?
N1 C9 N2 113.72(13) . . ?
N1 C9 C10 108.13(14) . . ?
N1 C9 H9 108.6 . . ?
N2 C9 C10 109.17(13) . . ?
N2 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C8 C3 C2 108.85(16) . . ?
C8 C3 C4 120.9(2) . . ?
C4 C3 C2 130.2(2) . . ?
C18 C13 S1 119.85(15) . . ?
C18 C13 C14 120.64(17) . . ?
C14 C13 S1 119.47(14) . . ?
C3 C8 C1 108.06(16) . . ?
C3 C8 C7 121.9(2) . . ?
C7 C8 C1 130.0(2) . . ?
C13 C18 H18 120.6 . . ?
C13 C18 C17 118.77(19) . . ?
C17 C18 H18 120.6 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.64(17) . . ?
C15 C14 H14 120.2 . . ?
C17 C16 C15 118.25(18) . . ?
C17 C16 C19 121.3(2) . . ?
C15 C16 C19 120.5(2) . . ?
C18 C17 C16 121.84(18) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C14 C15 C16 120.84(18) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 H4 121.3 . . ?
C8 C7 H7 121.6 . . ?
C8 C7 C6 116.7(3) . . ?
C6 C7 H7 121.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
O4 C11 C12 109.50(19) . . ?
O4 C11 H11A 109.8 . . ?
O4 C11 H11B 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?

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
S1 N1 C9 N2 -74.49(17) . . . . ?
S1 N1 C9 C10 164.10(11) . . . . ?
S1 C13 C18 C17 -177.96(16) . . . . ?
S1 C13 C14 C15 179.01(14) . . . . ?
O1 C1 C8 C3 -179.48(19) . . . . ?
O1 C1 C8 C7 2.6(4) . . . . ?
O3 C10 C9 N1 -2.6(2) . . . . ?
O3 C10 C9 N2 -126.79(18) . . . . ?
O2 C2 C3 C8 178.5(2) . . . . ?
O2 C2 C3 C4 -3.1(4) . . . . ?
N1 S1 C13 C18 -129.51(16) . . . . ?
N1 S1 C13 C14 52.84(17) . . . . ?
N2 C2 C3 C8 -0.9(2) . . . . ?
N2 C2 C3 C4 177.6(2) . . . . ?
N2 C1 C8 C3 0.4(2) . . . . ?
N2 C1 C8 C7 -177.6(2) . . . . ?
O6 S1 N1 C9 -47.33(15) . . . . ?
O6 S1 C13 C18 -13.93(18) . . . . ?
O6 S1 C13 C14 168.42(15) . . . . ?
O4 C10 C9 N1 177.39(13) . . . . ?
O4 C10 C9 N2 53.20(18) . . . . ?
O5 S1 N1 C9 -176.43(13) . . . . ?
O5 S1 C13 C18 117.77(17) . . . . ?
O5 S1 C13 C14 -59.88(17) . . . . ?
C10 O4 C11 C12 102.6(2) . . . . ?
C2 N2 C1 O1 178.91(17) . . . . ?
C2 N2 C1 C8 -0.94(19) . . . . ?
C2 N2 C9 N1 105.09(18) . . . . ?
C2 N2 C9 C10 -134.08(17) . . . . ?
C2 C3 C8 C1 0.3(2) . . . . ?
C2 C3 C8 C7 178.47(19) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
C1 N2 C2 O2 -178.26(18) . . . . ?
C1 N2 C2 C3 1.11(19) . . . . ?
C1 N2 C9 N1 -65.3(2) . . . . ?
C1 N2 C9 C10 55.6(2) . . . . ?
C1 C8 C7 C6 177.8(2) . . . . ?
C9 N2 C2 O2 10.6(3) . . . . ?
C9 N2 C2 C3 -170.08(15) . . . . ?
C9 N2 C1 O1 -9.5(3) . . . . ?
C9 N2 C1 C8 170.63(14) . . . . ?
C3 C8 C7 C6 0.1(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C13 S1 N1 C9 68.56(15) . . . . ?
C13 C18 C17 C16 -1.1(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C8 C3 C4 C5 -0.2(3) . . . . ?
C8 C7 C6 C5 0.3(4) . . . . ?
C18 C13 C14 C15 1.4(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C17 C16 C15 C14 -0.4(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C4 C3 C8 C1 -178.30(18) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C19 C16 C17 C18 -177.4(2) . . . . ?
C19 C16 C15 C14 178.47(19) . . . . ?
C11 O4 C10 O3 8.2(3) . . . . ?
C11 O4 C10 C9 -171.80(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
