# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_ODJ19_78_a
_database_code_depnum_ccdc_archive 'CCDC 2351518'
loop_
_audit_author_name
_audit_author_address
'Hyeseung Lee'
;College of Pharmacy, Seoul National University
South Korea
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-08-14 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         'C22 H22 N2 O6 S'
_chemical_formula_sum            'C22 H22 N2 O6 S'
_chemical_formula_weight         442.47

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.8856(10)
_cell_length_b                   13.443(2)
_cell_length_c                   26.710(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2113.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4405
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      25.81

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(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            43950
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_av_R_equivalents  0.1348
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5242
_reflns_number_gt                2737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0818P)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_abs_structure_details 
; 
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5242
_refine_ls_number_parameters     318
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1510
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.061
_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 0.5131(3) 0.58647(11) 0.57794(5) 0.0487(4) Uani 1 1 d . . . . .
O1 O 0.7417(7) 0.5748(3) 0.56109(15) 0.0604(12) Uani 1 1 d . . . . .
O2 O 0.3392(8) 0.5229(3) 0.55936(14) 0.0612(12) Uani 1 1 d . . . . .
O3 O 0.8026(6) 0.6769(3) 0.65436(13) 0.0480(10) Uani 1 1 d . . . . .
O4 O 0.8609(6) 0.6185(3) 0.74934(13) 0.0501(11) Uani 1 1 d . . . . .
H4O H 0.935679 0.656823 0.731373 0.075 Uiso 1 1 calc R U . . .
O5 O 0.9177(8) 0.3650(3) 0.7787(2) 0.0740(14) Uani 1 1 d . . . . .
O6 O 0.7346(7) 0.2278(3) 0.78543(15) 0.0549(11) Uani 1 1 d . . . . .
N1 N 0.5117(8) 0.5657(3) 0.64199(15) 0.0425(10) Uani 1 1 d . . . . .
N2 N 0.7448(8) 0.3178(3) 0.78804(16) 0.0425(11) Uani 1 1 d . . . . .
C1 C 0.2022(15) 1.0107(5) 0.5552(3) 0.079(2) Uani 1 1 d . . . . .
H1A H 0.330061 1.051765 0.545220 0.118 Uiso 1 1 calc R U . . .
H1B H 0.141948 1.034624 0.586746 0.118 Uiso 1 1 calc R U . . .
H1C H 0.084866 1.014215 0.529708 0.118 Uiso 1 1 calc R U . . .
C2 C 0.2784(11) 0.9059(5) 0.5610(2) 0.0534(15) Uani 1 1 d . . . . .
C3 C 0.4938(12) 0.8762(4) 0.5434(2) 0.0555(16) Uani 1 1 d . . . . .
H3 H 0.588391 0.922984 0.527565 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5685(10) 0.7787(4) 0.54920(19) 0.0497(15) Uani 1 1 d . . . . .
H4 H 0.712704 0.759409 0.537617 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4266(9) 0.7106(4) 0.57232(19) 0.0429(13) Uani 1 1 d . . . . .
C6 C 0.2112(10) 0.7380(5) 0.5889(2) 0.0517(15) Uani 1 1 d . . . . .
H6 H 0.113566 0.690839 0.603427 0.062 Uiso 1 1 calc R U . . .
C7 C 0.1440(11) 0.8354(5) 0.5835(2) 0.0576(16) Uani 1 1 d . . . . .
H7 H 0.000650 0.854463 0.595680 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6759(9) 0.6115(4) 0.67115(19) 0.0394(12) Uani 1 1 d . . . . .
C9 C 0.6895(9) 0.5784(4) 0.72226(19) 0.0392(12) Uani 1 1 d . . . . .
C10 C 0.5391(9) 0.5129(4) 0.74291(18) 0.0373(12) Uani 1 1 d . . . . .
C11 C 0.3604(10) 0.4784(4) 0.7111(2) 0.0480(14) Uani 1 1 d . . . . .
H11 H 0.246888 0.437252 0.724690 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3499(10) 0.5030(4) 0.6626(2) 0.0510(15) Uani 1 1 d . . . . .
H12 H 0.232470 0.477710 0.642443 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5513(9) 0.4841(4) 0.79741(17) 0.0390(12) Uani 1 1 d . . . . .
H13 H 0.701451 0.505692 0.810071 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5369(9) 0.3726(4) 0.8047(2) 0.0423(13) Uani 1 1 d . . . . .
H14A H 0.510995 0.358705 0.840294 0.051 Uiso 1 1 calc R U . . .
H14B H 0.405656 0.347260 0.786091 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3693(10) 0.5373(4) 0.8291(2) 0.0452(14) Uani 1 1 d . . . . .
H15A H 0.219850 0.528533 0.813536 0.054 Uiso 1 1 calc R U . . .
H15B H 0.364144 0.507764 0.862616 0.054 Uiso 1 1 calc R U . . .
C16 C 0.4231(11) 0.6485(4) 0.8333(2) 0.0600(18) Uani 1 1 d . . . . .
H16A H 0.580919 0.656148 0.844402 0.072 Uiso 1 1 calc R U . A 1
H16B H 0.410456 0.678638 0.800036 0.072 Uiso 1 1 calc R U . A 1
C17A C 0.2712(12) 0.7043(4) 0.8688(2) 0.0554(16) Uani 0.811(10) 1 d . . P B 1
C18A C 0.0579(15) 0.7352(6) 0.8549(3) 0.060(2) Uani 0.811(10) 1 d . . P B 1
H18A H 0.005254 0.720257 0.822578 0.072 Uiso 0.811(10) 1 calc R U P B 1
C19A C -0.0812(16) 0.7875(6) 0.8869(4) 0.073(3) Uani 0.811(10) 1 d . . P B 1
H19A H -0.229266 0.804941 0.877109 0.087 Uiso 0.811(10) 1 calc R U P B 1
C20A C -0.0002(19) 0.8143(6) 0.9341(3) 0.106(3) Uani 0.811(10) 1 d . . P B 1
H20A H -0.088816 0.854391 0.955278 0.127 Uiso 0.811(10) 1 calc R U P B 1
C21A C 0.198(2) 0.7836(10) 0.9486(5) 0.105(4) Uani 0.811(10) 1 d . U P B 1
H21A H 0.248814 0.798245 0.981142 0.126 Uiso 0.811(10) 1 calc R U P B 1
C22A C 0.339(2) 0.7286(10) 0.9161(5) 0.089(4) Uani 0.811(10) 1 d . U P B 1
H22A H 0.482618 0.708001 0.927340 0.107 Uiso 0.811(10) 1 calc R U P B 1
C17B C 0.2712(12) 0.7043(4) 0.8688(2) 0.0554(16) Uani 0.189(10) 1 d . . P B 2
C18B C 0.226(7) 0.800(3) 0.8570(18) 0.087(15) Uani 0.189(10) 1 d . . P B 2
H18B H 0.270649 0.824138 0.825470 0.105 Uiso 0.189(10) 1 calc R U P B 2
C19B C 0.121(6) 0.860(3) 0.8883(15) 0.072(12) Uani 0.189(10) 1 d . U P B 2
H19B H 0.120830 0.928971 0.882997 0.086 Uiso 0.189(10) 1 calc R U P B 2
C20B C -0.0002(19) 0.8143(6) 0.9341(3) 0.106(3) Uani 0.189(10) 1 d . . P B 2
H20B H -0.137366 0.837463 0.947801 0.127 Uiso 0.189(10) 1 calc R U P B 2
C21B C 0.118(5) 0.738(2) 0.9511(12) 0.036(8) Uani 0.189(10) 1 d . U P B 2
H21B H 0.121575 0.723979 0.985582 0.044 Uiso 0.189(10) 1 calc R U P B 2
C22B C 0.242(7) 0.675(3) 0.9162(16) 0.068(13) Uani 0.189(10) 1 d . . P B 2
H22B H 0.300806 0.613172 0.926931 0.082 Uiso 0.189(10) 1 calc R U P B 2


_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 O2 1.423(4) . ?
S1 O1 1.427(4) . ?
S1 N1 1.733(4) . ?
S1 C5 1.751(6) . ?
O3 C8 1.237(6) . ?
O4 C9 1.353(6) . ?
O4 H4O 0.8300 . ?
O5 N2 1.225(6) . ?
O6 N2 1.214(6) . ?
N1 C8 1.385(6) . ?
N1 C12 1.385(7) . ?
N2 C14 1.496(7) . ?
C1 C2 1.487(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C7 1.373(9) . ?
C2 C3 1.409(9) . ?
C3 C4 1.391(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(8) . ?
C6 C7 1.376(8) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.438(7) . ?
C9 C10 1.365(7) . ?
C10 C11 1.429(8) . ?
C10 C13 1.508(7) . ?
C11 C12 1.340(8) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.514(7) . ?
C13 C15 1.541(7) . ?
C13 H13 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.532(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17B 1.504(8) . ?
C16 C17A 1.504(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17A C22A 1.364(12) . ?
C17A C18A 1.374(10) . ?
C18A C19A 1.376(12) . ?
C18A H18A 0.9400 . ?
C19A C20A 1.394(12) . ?
C19A H19A 0.9400 . ?
C20A C21A 1.298(15) . ?
C20A H20A 0.9400 . ?
C21A C22A 1.408(16) . ?
C21A H21A 0.9400 . ?
C22A H22A 0.9400 . ?
C17B C22B 1.34(4) . ?
C17B C18B 1.35(4) . ?
C18B C19B 1.32(5) . ?
C18B H18B 0.9400 . ?
C19B C20B 1.54(4) . ?
C19B H19B 0.9400 . ?
C20B C21B 1.32(3) . ?
C20B H20B 0.9400 . ?
C21B C22B 1.46(5) . ?
C21B H21B 0.9400 . ?
C22B H22B 0.9400 . ?

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
O2 S1 O1 120.2(3) . . ?
O2 S1 N1 104.1(2) . . ?
O1 S1 N1 107.4(2) . . ?
O2 S1 C5 109.5(3) . . ?
O1 S1 C5 110.6(3) . . ?
N1 S1 C5 103.7(2) . . ?
C9 O4 H4O 109.5 . . ?
C8 N1 C12 121.7(4) . . ?
C8 N1 S1 118.7(3) . . ?
C12 N1 S1 119.5(4) . . ?
O6 N2 O5 123.0(5) . . ?
O6 N2 C14 117.9(5) . . ?
O5 N2 C14 119.1(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.0(6) . . ?
C7 C2 C1 121.7(6) . . ?
C3 C2 C1 120.3(6) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.1(6) . . ?
C4 C5 S1 119.5(4) . . ?
C6 C5 S1 119.3(4) . . ?
C7 C6 C5 118.7(6) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C2 C7 C6 122.5(6) . . ?
C2 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
O3 C8 N1 122.1(4) . . ?
O3 C8 C9 122.0(5) . . ?
N1 C8 C9 115.8(4) . . ?
O4 C9 C10 121.6(5) . . ?
O4 C9 C8 115.2(5) . . ?
C10 C9 C8 123.2(5) . . ?
C9 C10 C11 116.5(5) . . ?
C9 C10 C13 121.7(5) . . ?
C11 C10 C13 121.6(5) . . ?
C12 C11 C10 121.9(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 N1 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
N1 C12 H12 119.9 . . ?
C10 C13 C14 112.1(4) . . ?
C10 C13 C15 112.2(4) . . ?
C14 C13 C15 110.5(4) . . ?
C10 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C15 C13 H13 107.2 . . ?
N2 C14 C13 113.8(5) . . ?
N2 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C13 110.5(5) . . ?
C16 C15 H15A 109.6 . . ?
C13 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C13 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17B C16 C15 114.2(5) . . ?
C17A C16 C15 114.2(5) . . ?
C17A C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17A C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C22A C17A C18A 116.4(8) . . ?
C22A C17A C16 122.0(8) . . ?
C18A C17A C16 121.6(6) . . ?
C17A C18A C19A 122.0(7) . . ?
C17A C18A H18A 119.0 . . ?
C19A C18A H18A 119.0 . . ?
C18A C19A C20A 119.3(8) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A H19A 120.3 . . ?
C21A C20A C19A 119.7(9) . . ?
C21A C20A H20A 120.2 . . ?
C19A C20A H20A 120.2 . . ?
C20A C21A C22A 120.8(11) . . ?
C20A C21A H21A 119.6 . . ?
C22A C21A H21A 119.6 . . ?
C17A C22A C21A 121.7(11) . . ?
C17A C22A H22A 119.2 . . ?
C21A C22A H22A 119.2 . . ?
C22B C17B C18B 119(3) . . ?
C22B C17B C16 121.6(16) . . ?
C18B C17B C16 116.3(18) . . ?
C19B C18B C17B 122(4) . . ?
C19B C18B H18B 119.1 . . ?
C17B C18B H18B 119.1 . . ?
C18B C19B C20B 119(4) . . ?
C18B C19B H19B 120.7 . . ?
C20B C19B H19B 120.7 . . ?
C21B C20B C19B 110(2) . . ?
C21B C20B H20B 125.1 . . ?
C19B C20B H20B 125.1 . . ?
C20B C21B C22B 120(3) . . ?
C20B C21B H21B 120.1 . . ?
C22B C21B H21B 120.1 . . ?
C17B C22B C21B 120(3) . . ?
C17B C22B H22B 120.2 . . ?
C21B C22B H22B 120.2 . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061

