# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_AHIC326
_database_code_depnum_ccdc_archive 'CCDC 2045193'
loop_
_audit_author_name
_audit_author_address
'Ha-Jin Lee'
;Korea Basic Science Institute
South Korea
;
_audit_update_record             
;
2020-11-18 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O4 S'
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        Cc
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   13.738(13)
_cell_length_b                   15.885(13)
_cell_length_c                   7.706(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.13(4)
_cell_angle_gamma                90
_cell_volume                     1569(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5377
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.07

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker 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  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10297
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.564
_diffrn_reflns_theta_max         28.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3782
_reflns_number_gt                3516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.963

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0388P)²+0.2434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1529 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_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 0.40962(5) 0.26168(4) 0.03625(7) 0.03335(15) Uani 1 1 d . . . . .
O1 O 0.41877(16) 0.17492(12) 0.0774(3) 0.0440(5) Uani 1 1 d . . . . .
O2 O 0.43677(15) 0.29447(13) -0.1108(3) 0.0433(5) Uani 1 1 d . . . . .
O3 O 0.29064(13) 0.28339(11) -0.0037(3) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.26679(19) 0.36977(17) -0.0100(3) 0.0351(5) Uani 1 1 d . . . . .
C2 C 0.1643(2) 0.3903(2) -0.1052(4) 0.0449(7) Uani 1 1 d . . . . .
H2 H 0.1149 0.3481 -0.1603 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1351(2) 0.4735(2) -0.1188(4) 0.0497(7) Uani 1 1 d . . . . .
H3 H 0.0652 0.4880 -0.1854 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2066(2) 0.53631(19) -0.0364(4) 0.0434(6) Uani 1 1 d . . . . .
C5 C 0.3087(2) 0.51376(17) 0.0623(3) 0.0373(6) Uani 1 1 d . . . . .
H5 H 0.3575 0.5559 0.1210 0.045 Uiso 1 1 calc R U . . .
C6 C 0.34107(18) 0.43052(16) 0.0769(3) 0.0326(5) Uani 1 1 d . . . . .
C7 C 0.45439(18) 0.40862(14) 0.1741(3) 0.0302(5) Uani 1 1 d . . . . .
H7 H 0.4938 0.4241 0.0936 0.036 Uiso 1 1 calc R U . . .
O4 O 0.49264(12) 0.45391(10) 0.3386(2) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.59893(19) 0.43577(14) 0.4495(3) 0.0324(5) Uani 1 1 d . . . . .
H8A H 0.6333 0.4873 0.5116 0.039 Uiso 1 1 calc R U . . .
H8B H 0.6355 0.4160 0.3690 0.039 Uiso 1 1 calc R U . . .
C9 C 0.60586(18) 0.36978(14) 0.5932(3) 0.0280(5) Uani 1 1 d . . . . .
C10 C 0.53576(19) 0.30869(15) 0.5607(3) 0.0319(5) Uani 1 1 d . . . . .
H10 H 0.5442 0.2708 0.6587 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4453(2) 0.29375(15) 0.3857(3) 0.0322(5) Uani 1 1 d . . . . .
H11A H 0.4258 0.2341 0.3779 0.039 Uiso 1 1 calc R U . . .
H11B H 0.3855 0.3269 0.3878 0.039 Uiso 1 1 calc R U . . .
N1 N 0.46933(15) 0.31698(12) 0.2200(3) 0.0291(4) Uani 1 1 d . . . . .
C12 C 0.1749(3) 0.6275(2) -0.0571(5) 0.0575(9) Uani 1 1 d . . . . .
H12A H 0.2309 0.6613 0.0273 0.086 Uiso 1 1 calc R U . . .
H12B H 0.1124 0.6346 -0.0278 0.086 Uiso 1 1 calc R U . . .
H12C H 0.1611 0.6455 -0.1841 0.086 Uiso 1 1 calc R U . . .
C13 C 0.69261(18) 0.37800(13) 0.7750(3) 0.0280(5) Uani 1 1 d . . . . .
C14 C 0.7853(2) 0.41728(15) 0.7886(4) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.7934 0.4390 0.6811 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8661(2) 0.42485(17) 0.9593(4) 0.0431(6) Uani 1 1 d . . . . .
H15 H 0.9285 0.4516 0.9665 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8558(2) 0.39365(17) 1.1171(4) 0.0409(6) Uani 1 1 d . . . . .
H16 H 0.9110 0.3983 1.2323 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7637(2) 0.35533(17) 1.1057(4) 0.0397(6) Uani 1 1 d . . . . .
H17 H 0.7558 0.3340 1.2137 0.048 Uiso 1 1 calc R U . . .
C18 C 0.6832(2) 0.34811(16) 0.9364(4) 0.0343(5) Uani 1 1 d . . . . .
H18 H 0.6206 0.3223 0.9307 0.041 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 O1 1.410(2) . ?
S1 O2 1.414(2) . ?
S1 O3 1.588(2) . ?
S1 N1 1.616(2) . ?
O3 C1 1.408(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(4) . ?
C4 C12 1.505(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.505(4) . ?
C7 O4 1.386(3) . ?
C7 N1 1.495(3) . ?
C7 H7 0.9900 . ?
O4 C8 1.430(3) . ?
C8 C9 1.503(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.326(3) . ?
C9 C13 1.482(3) . ?
C10 C11 1.487(4) . ?
C10 H10 0.9400 . ?
C11 N1 1.477(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C18 1.380(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9400 . ?
C18 H18 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
O1 S1 O2 120.83(12) . . ?
O1 S1 O3 104.95(11) . . ?
O2 S1 O3 108.35(12) . . ?
O1 S1 N1 111.01(12) . . ?
O2 S1 N1 107.74(12) . . ?
O3 S1 N1 102.35(11) . . ?
C1 O3 S1 115.40(15) . . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 O3 115.6(2) . . ?
C6 C1 O3 122.6(2) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C12 120.4(3) . . ?
C3 C4 C12 121.1(3) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C7 120.3(2) . . ?
C1 C6 C7 121.9(2) . . ?
O4 C7 N1 108.35(18) . . ?
O4 C7 C6 108.6(2) . . ?
N1 C7 C6 111.84(19) . . ?
O4 C7 H7 109.3 . . ?
N1 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C7 O4 C8 114.26(18) . . ?
O4 C8 C9 111.1(2) . . ?
O4 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
O4 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C13 121.7(2) . . ?
C10 C9 C8 121.5(2) . . ?
C13 C9 C8 116.8(2) . . ?
C9 C10 C11 126.9(2) . . ?
C9 C10 H10 116.5 . . ?
C11 C10 H10 116.5 . . ?
N1 C11 C10 111.7(2) . . ?
N1 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 N1 C7 113.17(18) . . ?
C11 N1 S1 114.87(16) . . ?
C7 N1 S1 109.83(16) . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.9(2) . . ?
C18 C13 C9 121.1(2) . . ?
C14 C13 C9 120.9(2) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 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
O1 S1 O3 C1 167.16(17) . . . . ?
O2 S1 O3 C1 -62.49(19) . . . . ?
N1 S1 O3 C1 51.16(19) . . . . ?
S1 O3 C1 C2 158.13(19) . . . . ?
S1 O3 C1 C6 -23.0(3) . . . . ?
C6 C1 C2 C3 1.7(4) . . . . ?
O3 C1 C2 C3 -179.4(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C12 177.9(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C12 C4 C5 C6 -177.2(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 175.7(2) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
O3 C1 C6 C5 -179.7(2) . . . . ?
C2 C1 C6 C7 -177.2(2) . . . . ?
O3 C1 C6 C7 4.0(4) . . . . ?
C5 C6 C7 O4 45.2(3) . . . . ?
C1 C6 C7 O4 -138.6(2) . . . . ?
C5 C6 C7 N1 164.7(2) . . . . ?
C1 C6 C7 N1 -19.1(3) . . . . ?
N1 C7 O4 C8 55.5(2) . . . . ?
C6 C7 O4 C8 177.15(18) . . . . ?
C7 O4 C8 C9 -94.5(2) . . . . ?
O4 C8 C9 C10 32.7(3) . . . . ?
O4 C8 C9 C13 -145.3(2) . . . . ?
C13 C9 C10 C11 179.7(2) . . . . ?
C8 C9 C10 C11 1.9(4) . . . . ?
C9 C10 C11 N1 34.0(3) . . . . ?
C10 C11 N1 C7 -84.1(2) . . . . ?
C10 C11 N1 S1 148.66(17) . . . . ?
O4 C7 N1 C11 41.3(3) . . . . ?
C6 C7 N1 C11 -78.4(3) . . . . ?
O4 C7 N1 S1 171.10(15) . . . . ?
C6 C7 N1 S1 51.5(2) . . . . ?
O1 S1 N1 C11 -48.6(2) . . . . ?
O2 S1 N1 C11 177.02(17) . . . . ?
O3 S1 N1 C11 62.92(19) . . . . ?
O1 S1 N1 C7 -177.52(16) . . . . ?
O2 S1 N1 C7 48.11(19) . . . . ?
O3 S1 N1 C7 -65.99(17) . . . . ?
C10 C9 C13 C18 -26.8(3) . . . . ?
C8 C9 C13 C18 151.2(2) . . . . ?
C10 C9 C13 C14 154.3(2) . . . . ?
C8 C9 C13 C14 -27.8(3) . . . . ?
C18 C13 C14 C15 0.9(4) . . . . ?
C9 C13 C14 C15 179.9(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 0.6(4) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
C9 C13 C18 C17 179.8(2) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.034

