# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 1966217'
loop_
_audit_author_name
_audit_author_address
'Aymen Skhiri'
;Graduated school of engineering,Osaka University
Japan
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2023-02-12 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H18 N2 O3 S'
_chemical_formula_moiety         'C20 H18 N2 O3 S'
_chemical_formula_weight         366.43
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3302(6)
_cell_length_b                   7.6156(5)
_cell_length_c                   15.7854(10)
_cell_angle_alpha                85.339(5)
_cell_angle_beta                 82.972(6)
_cell_angle_gamma                83.511(6)
_cell_volume                     866.94(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2807
_cell_measurement_theta_min      5.61
_cell_measurement_theta_max      67.66
_cell_measurement_temperature    148
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.00
_exptl_absorpt_coefficient_mu    1.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_T_max  0.911

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      148
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7088
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_min         5.661
_diffrn_reflns_theta_full        68.160
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3093
_reflns_number_gt                2605
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1620
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     307
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1237P)²+0.0143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.40
_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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28482(8) 0.37492(7) 0.41973(4) 0.0418(2) Uani 1 1 d . . .
O1 O 0.1620(2) 0.3808(2) 0.20548(11) 0.0407(4) Uani 1 1 d . . .
O2 O 0.7608(2) 0.1099(2) 0.11878(11) 0.0432(4) Uani 1 1 d . . .
O3 O 0.9138(3) 0.1434(3) 0.38701(12) 0.0536(5) Uani 1 1 d . . .
N1 N 0.4536(2) 0.2895(2) 0.24492(12) 0.0315(4) Uani 1 1 d . . .
N2 N 0.8674(3) 0.0924(3) 0.25016(14) 0.0391(5) Uani 1 1 d . . .
C1 C 0.8440(4) 0.8021(4) -0.01197(17) 0.0433(6) Uani 1 1 d . . .
C2 C 0.7016(3) 0.7064(3) 0.04510(14) 0.0373(5) Uani 1 1 d . . .
C3 C 0.5140(3) 0.7407(3) 0.03366(15) 0.0391(6) Uani 1 1 d . . .
C4 C 0.3798(3) 0.6495(3) 0.08194(15) 0.0383(5) Uani 1 1 d . . .
C5 C 0.4372(3) 0.5191(3) 0.14278(14) 0.0332(5) Uani 1 1 d . . .
C6 C 0.6212(3) 0.4848(3) 0.15544(13) 0.0311(5) Uani 1 1 d . . .
C7 C 0.7563(3) 0.5772(3) 0.10736(15) 0.0349(5) Uani 1 1 d . . .
C8 C 0.3279(3) 0.3933(3) 0.19929(14) 0.0321(5) Uani 1 1 d . . .
C9 C 0.6460(3) 0.3333(3) 0.22221(14) 0.0322(5) Uani 1 1 d . . .
C10 C 0.7405(3) 0.3663(3) 0.30020(15) 0.0361(5) Uani 1 1 d . . .
C11 C 0.8499(3) 0.1918(3) 0.32105(16) 0.0407(6) Uani 1 1 d . . .
C12 C 0.7648(3) 0.1685(3) 0.18691(15) 0.0350(5) Uani 1 1 d . . .
C13 C 0.9761(4) -0.0793(4) 0.2432(2) 0.0544(7) Uani 1 1 d . . .
C14 C 0.4107(3) 0.1371(3) 0.30100(14) 0.0311(5) Uani 1 1 d . . .
C15 C 0.3377(3) 0.1581(3) 0.38654(14) 0.0321(5) Uani 1 1 d . . .
C16 C 0.3077(3) 0.0068(3) 0.44014(16) 0.0374(5) Uani 1 1 d . . .
C17 C 0.3490(3) -0.1595(3) 0.40922(16) 0.0394(6) Uani 1 1 d . . .
C18 C 0.4165(3) -0.1798(3) 0.32516(17) 0.0392(5) Uani 1 1 d . . .
C19 C 0.4473(3) -0.0309(3) 0.27039(15) 0.0361(5) Uani 1 1 d . . .
C20 C 0.1779(4) 0.3381(4) 0.52777(16) 0.0430(6) Uani 1 1 d . . .
H1 H 0.904(8) 0.861(7) 0.021(4) 0.127(19) Uiso 1 1 d . . .
H2 H 0.953(7) 0.718(6) -0.027(3) 0.113(16) Uiso 1 1 d . . .
H3 H 0.790(8) 0.877(7) -0.055(4) 0.15(2) Uiso 1 1 d . . .
H4 H 0.485(4) 0.837(4) -0.0133(19) 0.044(7) Uiso 1 1 d . . .
H5 H 0.249(3) 0.674(3) 0.0730(16) 0.029(6) Uiso 1 1 d . . .
H6 H 0.876(3) 0.551(3) 0.1169(15) 0.021(5) Uiso 1 1 d . . .
H7 H 0.833(4) 0.443(4) 0.2838(19) 0.047(8) Uiso 1 1 d . . .
H8 H 0.654(4) 0.405(3) 0.3463(18) 0.032(6) Uiso 1 1 d . . .
H9 H 0.902(6) -0.166(6) 0.234(3) 0.095(14) Uiso 1 1 d . . .
H10 H 1.033(8) -0.110(7) 0.300(4) 0.129(18) Uiso 1 1 d . . .
H11 H 1.082(6) -0.079(5) 0.203(3) 0.091(13) Uiso 1 1 d . . .
H12 H 0.489(3) -0.041(3) 0.2083(17) 0.030(6) Uiso 1 1 d . . .
H13 H 0.448(4) -0.285(4) 0.307(2) 0.046(8) Uiso 1 1 d . . .
H14 H 0.323(4) -0.264(4) 0.448(2) 0.053(8) Uiso 1 1 d . . .
H15 H 0.261(3) 0.020(3) 0.4965(18) 0.032(6) Uiso 1 1 d . . .
H16 H 0.069(5) 0.269(4) 0.524(2) 0.063(9) Uiso 1 1 d . . .
H17 H 0.138(4) 0.458(4) 0.547(2) 0.053(8) Uiso 1 1 d . . .
H18 H 0.260(4) 0.280(4) 0.5643(19) 0.044(7) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C15 1.760(2) . ?
S1 C20 1.802(3) . ?
O1 C8 1.222(3) . ?
O2 C12 1.202(3) . ?
O3 C11 1.207(3) . ?
N1 C8 1.378(3) . ?
N1 C14 1.441(3) . ?
N1 C9 1.480(3) . ?
N2 C12 1.375(3) . ?
N2 C11 1.387(4) . ?
N2 C13 1.457(4) . ?
C1 C2 1.506(3) . ?
C1 H1 0.90(6) . ?
C1 H2 0.98(5) . ?
C1 H3 0.94(6) . ?
C2 C7 1.394(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.384(3) . ?
C3 H4 1.03(3) . ?
C4 C5 1.391(3) . ?
C4 H5 0.98(2) . ?
C5 C6 1.381(3) . ?
C5 C8 1.488(3) . ?
C6 C7 1.392(3) . ?
C6 C9 1.509(3) . ?
C7 H6 0.91(2) . ?
C9 C10 1.536(3) . ?
C9 C12 1.547(3) . ?
C10 C11 1.506(4) . ?
C10 H7 0.94(3) . ?
C10 H8 0.95(3) . ?
C13 H9 0.93(5) . ?
C13 H10 1.04(6) . ?
C13 H11 0.94(5) . ?
C14 C19 1.390(3) . ?
C14 C15 1.405(3) . ?
C15 C16 1.395(3) . ?
C16 C17 1.383(4) . ?
C16 H15 0.92(3) . ?
C17 C18 1.373(4) . ?
C17 H14 0.99(3) . ?
C18 C19 1.391(3) . ?
C18 H13 0.87(3) . ?
C19 H12 1.00(3) . ?
C20 H16 1.01(4) . ?
C20 H17 0.99(3) . ?
C20 H18 0.94(3) . ?

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
C15 S1 C20 102.51(12) . . ?
C8 N1 C14 124.34(17) . . ?
C8 N1 C9 113.48(17) . . ?
C14 N1 C9 121.67(17) . . ?
C12 N2 C11 113.2(2) . . ?
C12 N2 C13 122.3(2) . . ?
C11 N2 C13 124.4(2) . . ?
C2 C1 H1 108(4) . . ?
C2 C1 H2 109(3) . . ?
H1 C1 H2 93(4) . . ?
C2 C1 H3 111(4) . . ?
H1 C1 H3 113(5) . . ?
H2 C1 H3 120(5) . . ?
C7 C2 C3 119.4(2) . . ?
C7 C2 C1 120.2(2) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H4 123.0(16) . . ?
C2 C3 H4 114.8(16) . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 H5 121.4(14) . . ?
C5 C4 H5 121.0(14) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 C8 109.38(19) . . ?
C4 C5 C8 129.6(2) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 C9 110.00(18) . . ?
C7 C6 C9 128.4(2) . . ?
C6 C7 C2 118.3(2) . . ?
C6 C7 H6 119.3(14) . . ?
C2 C7 H6 122.4(14) . . ?
O1 C8 N1 125.77(19) . . ?
O1 C8 C5 128.7(2) . . ?
N1 C8 C5 105.57(18) . . ?
N1 C9 C6 101.56(16) . . ?
N1 C9 C10 113.17(18) . . ?
C6 C9 C10 117.53(18) . . ?
N1 C9 C12 108.57(17) . . ?
C6 C9 C12 113.33(18) . . ?
C10 C9 C12 102.76(18) . . ?
C11 C10 C9 104.2(2) . . ?
C11 C10 H7 103.3(18) . . ?
C9 C10 H7 110.1(18) . . ?
C11 C10 H8 113.2(15) . . ?
C9 C10 H8 112.0(15) . . ?
H7 C10 H8 113(2) . . ?
O3 C11 N2 124.6(3) . . ?
O3 C11 C10 127.3(3) . . ?
N2 C11 C10 108.09(19) . . ?
O2 C12 N2 125.5(2) . . ?
O2 C12 C9 126.7(2) . . ?
N2 C12 C9 107.6(2) . . ?
N2 C13 H9 111(3) . . ?
N2 C13 H10 107(3) . . ?
H9 C13 H10 110(4) . . ?
N2 C13 H11 114(2) . . ?
H9 C13 H11 111(4) . . ?
H10 C13 H11 103(4) . . ?
C19 C14 C15 120.42(19) . . ?
C19 C14 N1 119.4(2) . . ?
C15 C14 N1 120.12(19) . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 S1 123.49(19) . . ?
C14 C15 S1 118.04(15) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H15 121.0(16) . . ?
C15 C16 H15 118.6(16) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H14 120.3(19) . . ?
C16 C17 H14 118.6(19) . . ?
C17 C18 C19 119.6(2) . . ?
C17 C18 H13 121(2) . . ?
C19 C18 H13 120(2) . . ?
C14 C19 C18 120.0(2) . . ?
C14 C19 H12 118.6(14) . . ?
C18 C19 H12 121.4(14) . . ?
S1 C20 H16 106(2) . . ?
S1 C20 H17 104.9(18) . . ?
H16 C20 H17 112(3) . . ?
S1 C20 H18 112.8(18) . . ?
H16 C20 H18 112(2) . . ?
H17 C20 H18 108(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
C7 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C8 -175.6(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C8 C5 C6 C7 176.6(2) . . . . ?
C4 C5 C6 C9 -177.8(2) . . . . ?
C8 C5 C6 C9 -0.3(3) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C9 C6 C7 C2 176.1(2) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C1 C2 C7 C6 -176.4(2) . . . . ?
C14 N1 C8 O1 6.8(4) . . . . ?
C9 N1 C8 O1 178.7(2) . . . . ?
C14 N1 C8 C5 -173.1(2) . . . . ?
C9 N1 C8 C5 -1.2(2) . . . . ?
C6 C5 C8 O1 -179.0(2) . . . . ?
C4 C5 C8 O1 -1.8(4) . . . . ?
C6 C5 C8 N1 0.9(2) . . . . ?
C4 C5 C8 N1 178.1(2) . . . . ?
C8 N1 C9 C6 1.0(2) . . . . ?
C14 N1 C9 C6 173.13(19) . . . . ?
C8 N1 C9 C10 127.9(2) . . . . ?
C14 N1 C9 C10 -60.0(3) . . . . ?
C8 N1 C9 C12 -118.7(2) . . . . ?
C14 N1 C9 C12 53.5(3) . . . . ?
C5 C6 C9 N1 -0.3(2) . . . . ?
C7 C6 C9 N1 -177.0(2) . . . . ?
C5 C6 C9 C10 -124.3(2) . . . . ?
C7 C6 C9 C10 59.0(3) . . . . ?
C5 C6 C9 C12 115.9(2) . . . . ?
C7 C6 C9 C12 -60.7(3) . . . . ?
N1 C9 C10 C11 97.0(2) . . . . ?
C6 C9 C10 C11 -145.06(19) . . . . ?
C12 C9 C10 C11 -19.9(2) . . . . ?
C12 N2 C11 O3 173.0(2) . . . . ?
C13 N2 C11 O3 -4.5(4) . . . . ?
C12 N2 C11 C10 -7.3(2) . . . . ?
C13 N2 C11 C10 175.2(2) . . . . ?
C9 C10 C11 O3 -162.9(2) . . . . ?
C9 C10 C11 N2 17.5(2) . . . . ?
C11 N2 C12 O2 178.1(2) . . . . ?
C13 N2 C12 O2 -4.4(4) . . . . ?
C11 N2 C12 C9 -6.2(2) . . . . ?
C13 N2 C12 C9 171.4(2) . . . . ?
N1 C9 C12 O2 72.1(3) . . . . ?
C6 C9 C12 O2 -39.9(3) . . . . ?
C10 C9 C12 O2 -167.8(2) . . . . ?
N1 C9 C12 N2 -103.61(19) . . . . ?
C6 C9 C12 N2 144.35(18) . . . . ?
C10 C9 C12 N2 16.5(2) . . . . ?
C8 N1 C14 C19 96.2(3) . . . . ?
C9 N1 C14 C19 -75.2(3) . . . . ?
C8 N1 C14 C15 -85.7(3) . . . . ?
C9 N1 C14 C15 103.0(2) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
N1 C14 C15 C16 -176.44(19) . . . . ?
C19 C14 C15 S1 -177.14(16) . . . . ?
N1 C14 C15 S1 4.8(3) . . . . ?
C20 S1 C15 C16 -3.9(2) . . . . ?
C20 S1 C15 C14 174.87(18) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
S1 C15 C16 C17 178.62(18) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C19 1.2(4) . . . . ?
C15 C14 C19 C18 -1.8(3) . . . . ?
N1 C14 C19 C18 176.3(2) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
