# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_lj-0704
_database_code_depnum_ccdc_archive 'CCDC 2190019'
loop_
_audit_author_name
_audit_author_address
'mingming zhao'
;Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_audit_creation_date             2022-07-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.211(C13 H14 N2 O3 S)'
_chemical_formula_sum            'C H N O S'
_chemical_formula_weight         75.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O H S '
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.5249(3)
_cell_length_b                   5.74470(10)
_cell_length_c                   12.9917(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.935(2)
_cell_angle_gamma                90
_cell_volume                     1307.76(4)
_cell_formula_units_Z            19
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.1130
_cell_measurement_theta_min      5.0390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             722
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6834
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.734
_diffrn_reflns_theta_min         5.048
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -31.00   0.50    0.50    --    0.90 -36.00  21.00   50
  2  ω     10.00  35.00   0.50    0.50    --    0.90  36.00 178.00   50
  3  ω     48.00  73.00   0.50    0.50    --  105.10 -36.00  21.00   50
  4  ω    138.00 182.00   0.50    0.50    --  105.10  36.00 178.00   88
  5  ω    -39.00  13.00   0.50    0.50    --   -0.90 -82.00 120.00  104
  6  ω    -37.00  26.00   0.50    0.50    --   -0.90 -82.00  30.00  126
  7  ω    -47.00 -13.00   0.50    0.50    --   -0.90 -77.00-180.00   68
  8  ω     82.00 127.00   0.50    0.50    --  105.10  82.00 120.00   90
  9  ω    150.00 191.00   0.50    0.50    --  105.10  38.00 -60.00   82
 10  ω     82.00 194.00   0.50    0.50    --  105.10  82.00  90.00  224
 11  ω     75.00 119.00   0.50    0.50    --  105.10 -77.00 150.00   88
 12  ω    110.00 136.00   0.50    0.50    --  105.10  38.00 -60.00   52
 13  ω     98.00 123.00   0.50    0.50    --  105.10  38.00  60.00   50
 14  ω    161.00 187.00   0.50    0.50    --  105.10  38.00  60.00   52
 15  ω     73.00 194.00   0.50    0.50    --  105.10  19.00-120.00  242
 16  ω     19.00 106.00   0.50    0.50    --  105.10 -38.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003178000
_diffrn_orient_matrix_UB_12      -0.0250901000
_diffrn_orient_matrix_UB_13      -0.1179187000
_diffrn_orient_matrix_UB_21      0.0779208000
_diffrn_orient_matrix_UB_22      0.1236714000
_diffrn_orient_matrix_UB_23      0.0312654000
_diffrn_orient_matrix_UB_31      0.0407478000
_diffrn_orient_matrix_UB_32      -0.2365693000
_diffrn_orient_matrix_UB_33      0.0288409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2488
_reflns_number_total             2654
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.111
_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)+(0.0622P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1029
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_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 0.31132(2) 0.26053(6) 0.64716(3) 0.02649(13) Uani 1 1 d . . . . .
O3 O 0.39120(5) 0.59007(17) 0.40106(7) 0.0281(2) Uani 1 1 d . . . . .
O2 O 0.36898(5) 0.63386(18) 0.56065(7) 0.0305(2) Uani 1 1 d . . . . .
O1 O 0.17342(7) -0.24493(17) 0.52033(9) 0.0351(3) Uani 1 1 d . . . . .
N2 N 0.31305(6) 0.3367(2) 0.43782(9) 0.0253(2) Uani 1 1 d . . . . .
N1 N 0.24019(6) 0.03944(19) 0.46851(9) 0.0245(2) Uani 1 1 d . . . . .
C11 C 0.35902(7) 0.5291(2) 0.47596(10) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.28949(7) 0.2229(2) 0.50645(10) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.14897(7) 0.1354(2) 0.28497(10) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.12404(7) 0.3313(2) 0.32635(11) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.1445 0.3668 0.4000 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21834(7) -0.0858(2) 0.54465(11) 0.0263(3) Uani 1 1 d . . . . .
C4 C 0.21197(7) -0.0222(2) 0.35331(10) 0.0250(3) Uani 1 1 d . . . . .
H4A H 0.1931 -0.1809 0.3464 0.030 Uiso 1 1 calc R U . . .
H4B H 0.2542 -0.0173 0.3246 0.030 Uiso 1 1 calc R U . . .
C6 C 0.11684(8) 0.0821(2) 0.17481(11) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.1325 -0.0505 0.1469 0.034 Uiso 1 1 calc R U . . .
C12 C 0.44274(8) 0.7875(2) 0.42869(11) 0.0280(3) Uani 1 1 d . . . . .
H12A H 0.4822 0.7618 0.4981 0.034 Uiso 1 1 calc R U . . .
H12B H 0.4151 0.9281 0.4337 0.034 Uiso 1 1 calc R U . . .
C9 C 0.06825(8) 0.4751(2) 0.25751(12) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.0518 0.6066 0.2854 0.036 Uiso 1 1 calc R U . . .
C8 C 0.06160(9) 0.2257(3) 0.10656(12) 0.0334(3) Uani 1 1 d . . . . .
H8 H 0.0408 0.1900 0.0330 0.040 Uiso 1 1 calc R U . . .
C1 C 0.25876(8) 0.0006(2) 0.65811(11) 0.0284(3) Uani 1 1 d . . . . .
H1A H 0.2934 -0.1175 0.6998 0.034 Uiso 1 1 calc R U . . .
H1B H 0.2220 0.0362 0.6947 0.034 Uiso 1 1 calc R U . . .
C10 C 0.03727(8) 0.4225(3) 0.14782(12) 0.0334(3) Uani 1 1 d . . . . .
H10 H 0.0003 0.5188 0.1020 0.040 Uiso 1 1 calc R U . . .
C13 C 0.47748(8) 0.8096(3) 0.33915(12) 0.0323(3) Uani 1 1 d . . . . .
H13A H 0.4377 0.8318 0.2709 0.048 Uiso 1 1 calc R U . . .
H13B H 0.5054 0.6705 0.3360 0.048 Uiso 1 1 calc R U . . .
H13C H 0.5114 0.9407 0.3535 0.048 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 C3 1.7529(13) . ?
S1 C1 1.8131(14) . ?
O3 C11 1.3422(15) . ?
O3 C12 1.4505(16) . ?
O2 C11 1.2145(16) . ?
O1 C2 1.2072(17) . ?
N2 C11 1.3850(17) . ?
N2 C3 1.2904(17) . ?
N1 C3 1.3770(17) . ?
N1 C2 1.3857(16) . ?
N1 C4 1.4597(16) . ?
C5 C7 1.3892(19) . ?
C5 C4 1.5158(18) . ?
C5 C6 1.3942(18) . ?
C7 H7 0.9300 . ?
C7 C9 1.3967(19) . ?
C2 C1 1.5045(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C8 1.387(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5064(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C10 1.388(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C3 S1 C1 91.85(6) . . ?
C11 O3 C12 115.86(10) . . ?
C3 N2 C11 117.62(11) . . ?
C3 N1 C2 117.09(11) . . ?
C3 N1 C4 121.87(11) . . ?
C2 N1 C4 121.04(11) . . ?
O3 C11 N2 108.36(11) . . ?
O2 C11 O3 123.70(12) . . ?
O2 C11 N2 127.92(12) . . ?
N2 C3 S1 130.01(10) . . ?
N2 C3 N1 118.31(12) . . ?
N1 C3 S1 111.68(9) . . ?
C7 C5 C4 123.14(12) . . ?
C7 C5 C6 119.37(12) . . ?
C6 C5 C4 117.46(11) . . ?
C5 C7 H7 120.0 . . ?
C5 C7 C9 120.08(12) . . ?
C9 C7 H7 120.0 . . ?
O1 C2 N1 122.86(12) . . ?
O1 C2 C1 126.02(12) . . ?
N1 C2 C1 111.12(11) . . ?
N1 C4 C5 114.02(10) . . ?
N1 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C6 H6 119.8 . . ?
C8 C6 C5 120.40(13) . . ?
C8 C6 H6 119.8 . . ?
O3 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
O3 C12 C13 106.66(11) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C7 C9 H9 119.9 . . ?
C10 C9 C7 120.20(13) . . ?
C10 C9 H9 119.9 . . ?
C6 C8 H8 119.9 . . ?
C6 C8 C10 120.15(14) . . ?
C10 C8 H8 119.9 . . ?
S1 C1 H1A 110.2 . . ?
S1 C1 H1B 110.2 . . ?
C2 C1 S1 107.71(9) . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C9 C10 C8 119.79(14) . . ?
C9 C10 H10 120.1 . . ?
C8 C10 H10 120.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 C2 C1 S1 -174.00(12) . . . . ?
N1 C2 C1 S1 7.08(13) . . . . ?
C11 O3 C12 C13 174.67(11) . . . . ?
C11 N2 C3 S1 -4.68(19) . . . . ?
C11 N2 C3 N1 176.30(11) . . . . ?
C3 S1 C1 C2 -6.85(10) . . . . ?
C3 N2 C11 O3 166.13(11) . . . . ?
C3 N2 C11 O2 -15.4(2) . . . . ?
C3 N1 C2 O1 177.43(12) . . . . ?
C3 N1 C2 C1 -3.62(16) . . . . ?
C3 N1 C4 C5 -77.53(14) . . . . ?
C5 C7 C9 C10 0.3(2) . . . . ?
C5 C6 C8 C10 -0.7(2) . . . . ?
C7 C5 C4 N1 4.50(17) . . . . ?
C7 C5 C6 C8 1.3(2) . . . . ?
C7 C9 C10 C8 0.3(2) . . . . ?
C2 N1 C3 S1 -1.85(15) . . . . ?
C2 N1 C3 N2 177.35(11) . . . . ?
C2 N1 C4 C5 102.61(14) . . . . ?
C4 N1 C3 S1 178.28(9) . . . . ?
C4 N1 C3 N2 -2.53(18) . . . . ?
C4 N1 C2 O1 -2.7(2) . . . . ?
C4 N1 C2 C1 176.26(11) . . . . ?
C4 C5 C7 C9 176.91(12) . . . . ?
C4 C5 C6 C8 -176.82(12) . . . . ?
C6 C5 C7 C9 -1.10(19) . . . . ?
C6 C5 C4 N1 -177.45(11) . . . . ?
C6 C8 C10 C9 -0.1(2) . . . . ?
C12 O3 C11 O2 2.61(19) . . . . ?
C12 O3 C11 N2 -178.88(11) . . . . ?
C1 S1 C3 N2 -173.87(13) . . . . ?
C1 S1 C3 N1 5.20(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.309
_oxdiff_exptl_absorpt_empirical_full_min 0.535
