# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_20240389_auto
_database_code_depnum_ccdc_archive 'CCDC 2354860'
loop_
_audit_author_name
_audit_author_address
'Yifan Guo'
;Zhengzhou university
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Cl N O5 S'
_chemical_formula_sum            'C18 H18 Cl N O5 S'
_chemical_formula_weight         395.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S1Cl1
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'
Cl Cl 0.3639 0.7018 '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                   8.4788(4)
_cell_length_b                   10.2215(7)
_cell_length_c                   11.5235(8)
_cell_angle_alpha                70.241(6)
_cell_angle_beta                 85.293(4)
_cell_angle_gamma                83.638(4)
_cell_volume                     933.06(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4870
_cell_measurement_theta_min      4.0630
_shelx_estimated_absorpt_T_max   0.746
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    3.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.040
_diffrn_reflns_theta_max         67.040
_diffrn_reflns_theta_min         4.081
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00-180.00   87
  2  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 120.00   87
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  30.00   93
  5  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00-180.00   93
  6  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -90.00   73
  7  ω      3.00  78.00   1.00    1.00    --   36.47-102.00 -86.00   75
  8  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 120.00   75
  9  ω     61.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   49
 10  ω     38.00 107.00   1.00    3.00    --  108.00-102.00 -86.00   69
 11  ω     63.00 176.00   1.00    3.00    --  108.00  15.00-180.00  113
 12  ω     43.00 120.00   1.00    3.00    --  108.00 -45.00-180.00   77
 13  ω     54.00  94.00   1.00    3.00    --  108.00 -94.00 -30.00   40
 14  ω     43.00 126.00   1.00    3.00    --  108.00 -45.00  90.00   83
 15  ω     38.00  94.00   1.00    3.00    --  108.00 -94.00  90.00   56
 16  ω    101.00 175.00   1.00    3.00    --  108.00  77.00-120.00   74
 17  ω    120.00 154.00   1.00    3.00    --  108.00 111.00  90.00   34
 18  ω    112.00 157.00   1.00    3.00    --  108.00  77.00-150.00   45
 19  ω     65.00 108.00   1.00    3.00    --  108.00-111.00  60.00   43
 20  ω     65.00 109.00   1.00    3.00    --  108.00-111.00-180.00   44
 21  ω     39.00 109.00   1.00    3.00    --  108.00 -45.00 -60.00   70
 22  ω     55.00 120.00   1.00    3.00    --  108.00 -77.00 150.00   65
 23  ω    150.00 178.00   1.00    3.00    --  108.00   0.00-150.00   28
 24  ω     41.00 124.00   1.00    3.00    --  108.00   0.00-150.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310961000
_diffrn_orient_matrix_UB_12      0.0518601000
_diffrn_orient_matrix_UB_13      0.1114393000
_diffrn_orient_matrix_UB_21      0.0612560000
_diffrn_orient_matrix_UB_22      0.1411752000
_diffrn_orient_matrix_UB_23      -0.0780999000
_diffrn_orient_matrix_UB_31      -0.1696476000
_diffrn_orient_matrix_UB_32      0.0568306000
_diffrn_orient_matrix_UB_33      -0.0413094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2792
_reflns_number_total             3330
_reflns_odcompleteness_completeness 99.97
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.023
_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)+(0.0786P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1347
_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. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cl1 Cl -0.48252(8) 0.23274(7) -0.00161(7) 0.0666(2) Uani 1 1 d . . . . .
S1 S -0.15235(6) 0.74317(6) 0.23621(6) 0.0473(2) Uani 1 1 d . . . . .
O1 O -0.2952(2) 0.7689(2) 0.3025(2) 0.0698(6) Uani 1 1 d . . . . .
O2 O -0.1504(3) 0.77432(19) 0.10574(18) 0.0658(5) Uani 1 1 d . . . . .
O3 O 0.17493(19) 0.51305(19) 0.43023(14) 0.0509(4) Uani 1 1 d . . . . .
O4 O 0.32167(18) 0.51796(19) 0.25803(14) 0.0494(4) Uani 1 1 d . . . . .
O5 O 0.1183(2) 0.27451(19) 0.3194(2) 0.0670(6) Uani 1 1 d . . . . .
N1 N -0.1023(2) 0.57443(19) 0.29616(17) 0.0400(4) Uani 1 1 d D . . . .
H1 H -0.113(3) 0.546(3) 0.3733(15) 0.039(6) Uiso 1 1 d D . . . .
C1 C -0.0005(3) 0.8280(2) 0.2691(2) 0.0432(5) Uani 1 1 d . . . . .
C2 C 0.1156(3) 0.8818(3) 0.1800(3) 0.0595(6) Uani 1 1 d . . . . .
H2 H 0.1107 0.8795 0.1004 0.071 Uiso 1 1 calc R . . . .
C3 C 0.2396(3) 0.9395(3) 0.2107(3) 0.0711(8) Uani 1 1 d . . . . .
H3 H 0.3180 0.9764 0.1508 0.085 Uiso 1 1 calc R . . . .
C4 C 0.2491(3) 0.9432(3) 0.3276(3) 0.0602(7) Uani 1 1 d . . . . .
C5 C 0.1308(3) 0.8894(3) 0.4150(3) 0.0588(6) Uani 1 1 d . . . . .
H5 H 0.1359 0.8921 0.4945 0.071 Uiso 1 1 calc R . . . .
C6 C 0.0047(3) 0.8317(3) 0.3873(2) 0.0513(6) Uani 1 1 d . . . . .
H6 H -0.0746 0.7963 0.4470 0.062 Uiso 1 1 calc R . . . .
C7 C 0.3848(4) 1.0052(4) 0.3609(4) 0.0880(12) Uani 1 1 d . . . . .
H7A H 0.4814 0.9470 0.3594 0.132 Uiso 1 1 calc GR . . . .
H7B H 0.3640 1.0114 0.4421 0.132 Uiso 1 1 calc GR . . . .
H7C H 0.3956 1.0968 0.3024 0.132 Uiso 1 1 calc GR . . . .
C8 C 0.0459(2) 0.5190(2) 0.24971(19) 0.0385(5) Uani 1 1 d . . . . .
H8 H 0.0669 0.5767 0.1637 0.046 Uiso 1 1 calc R . . . .
C9 C 0.1870(2) 0.5165(2) 0.32494(19) 0.0396(5) Uani 1 1 d . . . . .
C10 C 0.4693(3) 0.5087(3) 0.3201(2) 0.0552(6) Uani 1 1 d . . . . .
H10A H 0.4516 0.5612 0.3768 0.066 Uiso 1 1 calc R . . . .
H10B H 0.5512 0.5502 0.2590 0.066 Uiso 1 1 calc R . . . .
C11 C 0.5240(3) 0.3624(3) 0.3887(3) 0.0687(8) Uani 1 1 d . . . . .
H11A H 0.4435 0.3213 0.4497 0.103 Uiso 1 1 calc GR . . . .
H11B H 0.6199 0.3599 0.4285 0.103 Uiso 1 1 calc GR . . . .
H11C H 0.5442 0.3108 0.3323 0.103 Uiso 1 1 calc GR . . . .
C12 C 0.0307(3) 0.3682(2) 0.2549(2) 0.0429(5) Uani 1 1 d . . . . .
C13 C -0.0937(2) 0.3398(2) 0.1853(2) 0.0403(5) Uani 1 1 d . . . . .
C14 C -0.1828(2) 0.4454(2) 0.09723(19) 0.0403(5) Uani 1 1 d . . . . .
H14 H -0.1638 0.5383 0.0790 0.048 Uiso 1 1 calc R . . . .
C15 C -0.2984(3) 0.4111(2) 0.0378(2) 0.0438(5) Uani 1 1 d . . . . .
H15 H -0.3559 0.4807 -0.0220 0.053 Uiso 1 1 calc R . . . .
C16 C -0.3287(3) 0.2740(3) 0.0671(2) 0.0474(5) Uani 1 1 d . . . . .
C17 C -0.2408(3) 0.1684(3) 0.1513(3) 0.0555(6) Uani 1 1 d . . . . .
H17 H -0.2607 0.0758 0.1689 0.067 Uiso 1 1 calc R . . . .
C18 C -0.1226(3) 0.2018(2) 0.2092(2) 0.0501(6) Uani 1 1 d . . . . .
H18 H -0.0615 0.1308 0.2650 0.060 Uiso 1 1 calc R . . . .


_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
Cl1 C16 1.738(2) . ?
S1 O1 1.426(2) . ?
S1 O2 1.427(2) . ?
S1 N1 1.6470(19) . ?
S1 C1 1.761(2) . ?
O3 C9 1.198(3) . ?
O4 C9 1.323(3) . ?
O4 C10 1.470(3) . ?
O5 C12 1.213(3) . ?
N1 H1 0.837(16) . ?
N1 C8 1.457(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(4) . ?
C4 C5 1.380(4) . ?
C4 C7 1.507(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C9 1.527(3) . ?
C8 C12 1.542(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.478(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.484(3) . ?
C13 C14 1.403(3) . ?
C13 C18 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(3) . ?
C16 C17 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C18 H18 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
O1 S1 O2 120.35(13) . . ?
O1 S1 N1 105.38(11) . . ?
O1 S1 C1 109.04(11) . . ?
O2 S1 N1 106.55(11) . . ?
O2 S1 C1 108.19(12) . . ?
N1 S1 C1 106.50(10) . . ?
C9 O4 C10 117.00(17) . . ?
S1 N1 H1 112.5(17) . . ?
C8 N1 S1 117.47(15) . . ?
C8 N1 H1 112.9(17) . . ?
C2 C1 S1 120.17(19) . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 S1 118.66(18) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 C7 121.1(3) . . ?
C5 C4 C7 120.3(3) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8 109.0 . . ?
N1 C8 C9 112.45(17) . . ?
N1 C8 C12 109.58(17) . . ?
C9 C8 H8 109.0 . . ?
C9 C8 C12 107.87(17) . . ?
C12 C8 H8 109.0 . . ?
O3 C9 O4 125.56(19) . . ?
O3 C9 C8 123.78(19) . . ?
O4 C9 C8 110.66(17) . . ?
O4 C10 H10A 109.3 . . ?
O4 C10 H10B 109.3 . . ?
O4 C10 C11 111.5(2) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C8 118.8(2) . . ?
O5 C12 C13 121.5(2) . . ?
C13 C12 C8 119.71(18) . . ?
C14 C13 C12 123.2(2) . . ?
C18 C13 C12 117.97(19) . . ?
C18 C13 C14 118.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 Cl1 119.62(18) . . ?
C15 C16 C17 121.2(2) . . ?
C17 C16 Cl1 119.14(19) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(2) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?

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
Cl1 C16 C17 C18 -177.6(2) . . . . ?
S1 N1 C8 C9 91.79(19) . . . . ?
S1 N1 C8 C12 -148.24(15) . . . . ?
S1 C1 C2 C3 -175.6(2) . . . . ?
S1 C1 C6 C5 175.35(18) . . . . ?
O1 S1 N1 C8 -176.96(16) . . . . ?
O1 S1 C1 C2 -146.6(2) . . . . ?
O1 S1 C1 C6 37.2(2) . . . . ?
O2 S1 N1 C8 54.11(18) . . . . ?
O2 S1 C1 C2 -14.1(2) . . . . ?
O2 S1 C1 C6 169.75(18) . . . . ?
O5 C12 C13 C14 -171.1(2) . . . . ?
O5 C12 C13 C18 9.0(3) . . . . ?
N1 S1 C1 C2 100.2(2) . . . . ?
N1 S1 C1 C6 -76.0(2) . . . . ?
N1 C8 C9 O3 24.1(3) . . . . ?
N1 C8 C9 O4 -156.15(18) . . . . ?
N1 C8 C12 O5 -118.1(2) . . . . ?
N1 C8 C12 C13 59.7(2) . . . . ?
C1 S1 N1 C8 -61.21(18) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C7 179.6(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C7 C4 C5 C6 -180.0(3) . . . . ?
C8 C12 C13 C14 11.1(3) . . . . ?
C8 C12 C13 C18 -168.7(2) . . . . ?
C9 O4 C10 C11 83.7(3) . . . . ?
C9 C8 C12 O5 4.6(3) . . . . ?
C9 C8 C12 C13 -177.61(18) . . . . ?
C10 O4 C9 O3 2.7(4) . . . . ?
C10 O4 C9 C8 -176.99(19) . . . . ?
C12 C8 C9 O3 -96.8(3) . . . . ?
C12 C8 C9 O4 82.9(2) . . . . ?
C12 C13 C14 C15 -178.8(2) . . . . ?
C12 C13 C18 C17 177.4(2) . . . . ?
C13 C14 C15 C16 1.6(3) . . . . ?
C14 C13 C18 C17 -2.4(4) . . . . ?
C14 C15 C16 Cl1 176.25(17) . . . . ?
C14 C15 C16 C17 -2.9(4) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C13 1.1(4) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?

_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.835
####################################################################### 
# 
# 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_20240391_auto
_database_code_depnum_ccdc_archive 'CCDC 2354862'
loop_
_audit_author_name
_audit_author_address
'Yifan Guo'
;Zhengzhou university
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O5 S2'
_chemical_formula_sum            'C16 H17 N O5 S2'
_chemical_formula_weight         367.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S1Cl1
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                   9.7599(5)
_cell_length_b                   9.9262(7)
_cell_length_c                   10.5536(7)
_cell_angle_alpha                62.799(7)
_cell_angle_beta                 88.789(5)
_cell_angle_gamma                72.976(5)
_cell_volume                     861.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2395
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2090
_cell_measurement_theta_min      4.7390
_shelx_estimated_absorpt_T_max   0.751
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    3.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.753
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  90.00   93
  2  ω   -105.00  38.00   1.00    1.00    --  -33.50   0.00 120.00  143
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00-180.00   75
  5  ω     61.00 110.00   1.00    1.00    --   36.47 178.00 150.00   49
  6  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00  60.00   75
  7  ω     61.00 110.00   1.00    1.00    --   36.47 178.00 120.00   49
  8  ω     61.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   49
  9  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 -30.00   75
 10  ω    104.00 176.00   1.00    1.00    --  108.00 111.00 -90.00   72
 11  ω     40.00 109.00   1.00    1.00    --  108.00-111.00  30.00   69
 12  ω     82.00 178.00   1.00    1.00    --  108.00  30.00-120.00   96
 13  ω     37.00 123.00   1.00    1.00    --  108.00 -30.00 -60.00   86
 14  ω     66.00 109.00   1.00    1.00    --  108.00-111.00 150.00   43
 15  ω     89.00 177.00   1.00    1.00    --  108.00  45.00 -30.00   88
 16  ω    102.00 150.00   1.00    1.00    --  108.00  77.00  90.00   48
 17  ω    119.00 170.00   1.00    1.00    --  108.00  77.00   0.00   51
 18  ω     55.00 101.00   1.00    1.00    --  108.00 -61.00 -90.00   46
 19  ω     40.00  98.00   1.00    1.00    --  108.00-114.00 -32.00   58
 20  ω    123.00 171.00   1.00    1.00    --  108.00 111.00 -60.00   48
 21  ω     42.00 108.00   1.00    1.00    --  108.00-111.00-120.00   66
 22  ω     62.00 125.00   1.00    1.00    --  108.00 178.00   0.00   63
 23  ω    100.00 127.00   1.00    1.00    --  108.00  45.00  90.00   27
 24  ω     40.00 126.00   1.00    1.00    --  108.00 -61.00   0.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0407982000
_diffrn_orient_matrix_UB_12      0.1276150000
_diffrn_orient_matrix_UB_13      -0.1592053000
_diffrn_orient_matrix_UB_21      -0.0291124000
_diffrn_orient_matrix_UB_22      -0.1224195000
_diffrn_orient_matrix_UB_23      -0.0381296000
_diffrn_orient_matrix_UB_31      -0.1588275000
_diffrn_orient_matrix_UB_32      0.0511148000
_diffrn_orient_matrix_UB_33      0.0248754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2178
_reflns_number_total             3058
_reflns_odcompleteness_completeness 99.71
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0665
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²+0.0797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.2106
_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. Restrained distances
 C14-C13
 1.39 with sigma of 0.02
 C14-C15
 1.39 with sigma of 0.02
 C15-C16
 1.39 with sigma of 0.02
 H1-N1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.27479(10) 0.55216(11) 0.73157(9) 0.0452(3) Uani 1 1 d . . . . .
S2 S 0.42699(14) -0.10977(13) 0.80044(15) 0.0734(4) Uani 1 1 d . . . . .
O1 O 0.3844(3) 0.5676(3) 0.8049(3) 0.0570(7) Uani 1 1 d . . . . .
O2 O 0.1597(3) 0.5016(3) 0.8043(3) 0.0542(7) Uani 1 1 d . . . . .
O3 O 0.3532(3) 0.5544(3) 0.3808(3) 0.0530(7) Uani 1 1 d . . . . .
O4 O 0.1473(3) 0.5049(3) 0.3625(3) 0.0511(7) Uani 1 1 d . . . . .
O5 O 0.3780(4) 0.1841(4) 0.5255(3) 0.0679(9) Uani 1 1 d . . . . .
N1 N 0.3577(3) 0.4195(3) 0.6807(3) 0.0427(7) Uani 1 1 d D . . . .
H1 H 0.435(3) 0.438(4) 0.655(4) 0.051(12) Uiso 1 1 d D . . . .
C1 C 0.1983(4) 0.7326(4) 0.5733(4) 0.0450(9) Uani 1 1 d . . . . .
C2 C 0.0587(4) 0.7702(5) 0.5134(5) 0.0546(10) Uani 1 1 d . . . . .
H2 H 0.0016 0.7066 0.5609 0.065 Uiso 1 1 calc R . . . .
C3 C 0.0061(5) 0.9048(5) 0.3812(5) 0.0614(11) Uani 1 1 d . . . . .
H3 H -0.0874 0.9304 0.3403 0.074 Uiso 1 1 calc R . . . .
C4 C 0.0867(5) 1.0012(5) 0.3086(4) 0.0580(11) Uani 1 1 d . . . . .
C5 C 0.2250(5) 0.9626(5) 0.3735(5) 0.0599(11) Uani 1 1 d . . . . .
H5 H 0.2805 1.0286 0.3274 0.072 Uiso 1 1 calc R . . . .
C6 C 0.2819(4) 0.8292(5) 0.5040(4) 0.0508(9) Uani 1 1 d . . . . .
H6 H 0.3751 0.8044 0.5451 0.061 Uiso 1 1 calc R . . . .
C7 C 0.0270(6) 1.1442(6) 0.1633(5) 0.0867(16) Uani 1 1 d . . . . .
H7A H -0.0036 1.1108 0.0995 0.130 Uiso 1 1 calc GR . . . .
H7B H 0.1005 1.1926 0.1250 0.130 Uiso 1 1 calc GR . . . .
H7C H -0.0541 1.2202 0.1728 0.130 Uiso 1 1 calc GR . . . .
C8 C 0.2707(4) 0.3850(4) 0.5956(4) 0.0409(8) Uani 1 1 d . . . . .
H8 H 0.1726 0.4004 0.6221 0.049 Uiso 1 1 calc R . . . .
C9 C 0.2636(4) 0.4928(4) 0.4339(4) 0.0422(8) Uani 1 1 d . . . . .
C10 C 0.1366(5) 0.5856(5) 0.2051(4) 0.0605(11) Uani 1 1 d . . . . .
H10A H 0.1707 0.6770 0.1732 0.073 Uiso 1 1 calc R . . . .
H10B H 0.0364 0.6238 0.1638 0.073 Uiso 1 1 calc R . . . .
C11 C 0.2241(6) 0.4741(7) 0.1551(5) 0.0850(16) Uani 1 1 d . . . . .
H11A H 0.2117 0.5263 0.0520 0.127 Uiso 1 1 calc GR . . . .
H11B H 0.1932 0.3814 0.1905 0.127 Uiso 1 1 calc GR . . . .
H11C H 0.3243 0.4424 0.1906 0.127 Uiso 1 1 calc GR . . . .
C12 C 0.3390(4) 0.2099(5) 0.6246(4) 0.0477(9) Uani 1 1 d . . . . .
C13 C 0.3515(4) 0.0827(4) 0.7709(4) 0.0483(9) Uani 1 1 d D . . . .
C14 C 0.3041(4) 0.0890(4) 0.8971(4) 0.0457(9) Uani 1 1 d D . . . .
H14 H 0.2594 0.1816 0.9040 0.055 Uiso 1 1 calc R . . . .
C15 C 0.3361(6) -0.0679(6) 1.0098(5) 0.0728(13) Uani 1 1 d D . . . .
H15 H 0.3151 -0.0905 1.1024 0.087 Uiso 1 1 calc R . . . .
C16 C 0.3991(5) -0.1826(5) 0.9735(5) 0.0719(14) Uani 1 1 d D . . . .
H16 H 0.4248 -0.2912 1.0376 0.086 Uiso 1 1 calc R . . . .


_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 1.416(3) . ?
S1 O2 1.430(3) . ?
S1 N1 1.637(3) . ?
S1 C1 1.758(4) . ?
S2 C13 1.712(4) . ?
S2 C16 1.679(5) . ?
O3 C9 1.197(4) . ?
O4 C9 1.320(4) . ?
O4 C10 1.467(4) . ?
O5 C12 1.215(5) . ?
N1 H1 0.844(19) . ?
N1 C8 1.460(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.383(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 C5 1.391(6) . ?
C4 C7 1.506(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C9 1.534(5) . ?
C8 C12 1.550(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.480(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.458(5) . ?
C13 C14 1.424(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.342(7) . ?
C16 H16 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
O1 S1 O2 120.16(17) . . ?
O1 S1 N1 105.74(16) . . ?
O1 S1 C1 109.30(17) . . ?
O2 S1 N1 106.35(16) . . ?
O2 S1 C1 108.13(17) . . ?
N1 S1 C1 106.31(16) . . ?
C16 S2 C13 91.5(2) . . ?
C9 O4 C10 116.8(3) . . ?
S1 N1 H1 106(3) . . ?
C8 N1 S1 117.7(2) . . ?
C8 N1 H1 120(3) . . ?
C2 C1 S1 119.6(3) . . ?
C6 C1 S1 119.6(3) . . ?
C6 C1 C2 120.7(4) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 C7 120.8(4) . . ?
C5 C4 C7 121.5(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.0(4) . . ?
C5 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8 109.3 . . ?
N1 C8 C9 111.7(3) . . ?
N1 C8 C12 109.8(3) . . ?
C9 C8 H8 109.3 . . ?
C9 C8 C12 107.3(3) . . ?
C12 C8 H8 109.3 . . ?
O3 C9 O4 125.2(3) . . ?
O3 C9 C8 124.1(3) . . ?
O4 C9 C8 110.7(3) . . ?
O4 C10 H10A 109.6 . . ?
O4 C10 H10B 109.6 . . ?
O4 C10 C11 110.3(4) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C8 119.1(4) . . ?
O5 C12 C13 122.9(4) . . ?
C13 C12 C8 118.0(3) . . ?
C12 C13 S2 117.2(3) . . ?
C14 C13 S2 111.9(3) . . ?
C14 C13 C12 130.8(4) . . ?
C13 C14 H14 125.7 . . ?
C15 C14 C13 108.7(4) . . ?
C15 C14 H14 125.7 . . ?
C14 C15 H15 122.6 . . ?
C16 C15 C14 114.9(5) . . ?
C16 C15 H15 122.6 . . ?
S2 C16 H16 123.5 . . ?
C15 C16 S2 113.0(3) . . ?
C15 C16 H16 123.5 . . ?

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
S1 N1 C8 C9 91.0(3) . . . . ?
S1 N1 C8 C12 -150.2(3) . . . . ?
S1 C1 C2 C3 -173.5(3) . . . . ?
S1 C1 C6 C5 174.1(3) . . . . ?
S2 C13 C14 C15 0.6(4) . . . . ?
O1 S1 N1 C8 -177.1(2) . . . . ?
O1 S1 C1 C2 -155.2(3) . . . . ?
O1 S1 C1 C6 29.8(4) . . . . ?
O2 S1 N1 C8 54.1(3) . . . . ?
O2 S1 C1 C2 -22.8(4) . . . . ?
O2 S1 C1 C6 162.2(3) . . . . ?
O5 C12 C13 S2 0.8(5) . . . . ?
O5 C12 C13 C14 -175.5(4) . . . . ?
N1 S1 C1 C2 91.1(3) . . . . ?
N1 S1 C1 C6 -83.9(3) . . . . ?
N1 C8 C9 O3 24.9(5) . . . . ?
N1 C8 C9 O4 -156.5(3) . . . . ?
N1 C8 C12 O5 -119.5(4) . . . . ?
N1 C8 C12 C13 61.3(4) . . . . ?
C1 S1 N1 C8 -61.0(3) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C2 C3 C4 C7 178.5(4) . . . . ?
C3 C4 C5 C6 2.1(7) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C6 C1 C2 C3 1.4(6) . . . . ?
C7 C4 C5 C6 -177.9(4) . . . . ?
C8 C12 C13 S2 179.9(2) . . . . ?
C8 C12 C13 C14 3.6(6) . . . . ?
C9 O4 C10 C11 80.9(4) . . . . ?
C9 C8 C12 O5 2.0(5) . . . . ?
C9 C8 C12 C13 -177.1(3) . . . . ?
C10 O4 C9 O3 7.1(6) . . . . ?
C10 O4 C9 C8 -171.6(3) . . . . ?
C12 C8 C9 O3 -95.5(4) . . . . ?
C12 C8 C9 O4 83.2(4) . . . . ?
C12 C13 C14 C15 177.1(4) . . . . ?
C13 S2 C16 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C14 C15 C16 S2 0.8(6) . . . . ?
C16 S2 C13 C12 -177.2(3) . . . . ?
C16 S2 C13 C14 -0.2(3) . . . . ?

_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 4.109
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# 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_20240390_auto
_database_code_depnum_ccdc_archive 'CCDC 2354861'
loop_
_audit_author_name
_audit_author_address
'Yifan Guo'
;Zhengzhou university
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 F N O5 S'
_chemical_formula_sum            'C18 H18 F N O5 S'
_chemical_formula_weight         379.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S1Cl1
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'
F F 0.0727 0.0534 '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                   9.9859(6)
_cell_length_b                   10.0673(6)
_cell_length_c                   10.7587(7)
_cell_angle_alpha                114.717(6)
_cell_angle_beta                 93.857(5)
_cell_angle_gamma                106.344(5)
_cell_volume                     921.33(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4880
_cell_measurement_theta_min      4.6290
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6578
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         4.630
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00-120.00   87
  2  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 120.00   93
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -90.00   73
  5  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00  30.00   87
  6  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  60.00   73
  7  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 -90.00   75
  8  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 120.00   75
  9  ω     61.00 110.00   1.00    1.00    --   36.47 178.00-150.00   49
 10  ω     14.00 107.00   1.00    1.00    --   36.47  37.00 150.00   93
 11  ω    101.00 177.00   1.00    5.00    --  108.00  77.00  90.00   76
 12  ω     40.00 109.00   1.00    5.00    --  108.00-111.00 -90.00   69
 13  ω     39.00 103.00   1.00    5.00    --  108.00 -94.00 -60.00   64
 14  ω     41.00 109.00   1.00    5.00    --  108.00-111.00 150.00   68
 15  ω     68.00  95.00   1.00    5.00    --  108.00 -94.00-180.00   27
 16  ω     40.00  65.00   1.00    5.00    --  108.00 -77.00-120.00   25
 17  ω     39.00  65.00   1.00    5.00    --  108.00 -94.00-180.00   26
 18  ω    115.00 168.00   1.00    5.00    --  108.00  77.00-120.00   53
 19  ω    102.00 129.00   1.00    5.00    --  108.00 -77.00-120.00   27
 20  ω    105.00 169.00   1.00    5.00    --  108.00 111.00 -30.00   64
 21  ω     43.00 128.00   1.00    5.00    --  108.00 -30.00 150.00   85
 22  ω     69.00 109.00   1.00    5.00    --  108.00-111.00  90.00   40
 23  ω     36.00 145.00   1.00    5.00    --  108.00 -15.00 -90.00  109
 24  ω    118.00 145.00   1.00    5.00    --  108.00 111.00-180.00   27
 25  ω    103.00 175.00   1.00    5.00    --  108.00  61.00 -60.00   72
 26  ω     43.00 128.00   1.00    5.00    --  108.00 -61.00 -30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354045000
_diffrn_orient_matrix_UB_12      0.0356097000
_diffrn_orient_matrix_UB_13      0.1452702000
_diffrn_orient_matrix_UB_21      0.0527533000
_diffrn_orient_matrix_UB_22      0.1751224000
_diffrn_orient_matrix_UB_23      0.0413705000
_diffrn_orient_matrix_UB_31      -0.1517525000
_diffrn_orient_matrix_UB_32      -0.0137906000
_diffrn_orient_matrix_UB_33      -0.0566092000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             3273
_reflns_odcompleteness_completeness 99.70
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0855P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1615
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C14(H14), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.6998(3) -0.2204(4) 0.5712(3) 0.0567(7) Uani 1 1 d . . . . .
C2 C 0.7761(3) -0.3173(4) 0.5092(3) 0.0650(8) Uani 1 1 d . . . . .
H2 H 0.8712 -0.2911 0.5490 0.078 Uiso 1 1 calc R . . . .
C3 C 0.7092(4) -0.4528(4) 0.3879(4) 0.0746(9) Uani 1 1 d . . . . .
H3 H 0.7599 -0.5185 0.3461 0.089 Uiso 1 1 calc R . . . .
C4 C 0.5672(4) -0.4936(4) 0.3265(4) 0.0720(9) Uani 1 1 d . . . . .
C5 C 0.4945(4) -0.3969(4) 0.3915(4) 0.0775(10) Uani 1 1 d . . . . .
H5 H 0.3989 -0.4240 0.3526 0.093 Uiso 1 1 calc R . . . .
C6 C 0.5588(3) -0.2593(4) 0.5139(4) 0.0688(8) Uani 1 1 d . . . . .
H6 H 0.5074 -0.1947 0.5562 0.083 Uiso 1 1 calc R . . . .
C7 C 0.4947(5) -0.6424(5) 0.1922(4) 0.1014(14) Uani 1 1 d . . . . .
H7A H 0.4923 -0.6189 0.1145 0.152 Uiso 1 1 calc GR . . . .
H7B H 0.3990 -0.6903 0.1976 0.152 Uiso 1 1 calc GR . . . .
H7C H 0.5470 -0.7123 0.1795 0.152 Uiso 1 1 calc GR . . . .
C8 C 0.7818(3) 0.1164(3) 0.5756(3) 0.0538(6) Uani 1 1 d . . . . .
H8 H 0.6868 0.1033 0.5979 0.065 Uiso 1 1 calc R . . . .
C9 C 0.7652(3) 0.0095(4) 0.4205(3) 0.0562(7) Uani 1 1 d . . . . .
C10 C 0.6271(4) -0.0855(5) 0.1939(3) 0.0814(11) Uani 1 1 d . . . . .
H10A H 0.5266 -0.1224 0.1514 0.098 Uiso 1 1 calc R . . . .
H10B H 0.6575 -0.1752 0.1691 0.098 Uiso 1 1 calc R . . . .
C11 C 0.7109(6) 0.0180(6) 0.1400(4) 0.1134(16) Uani 1 1 d . . . . .
H11A H 0.8105 0.0528 0.1809 0.170 Uiso 1 1 calc GR . . . .
H11B H 0.6802 0.1062 0.1642 0.170 Uiso 1 1 calc GR . . . .
H11C H 0.6962 -0.0382 0.0400 0.170 Uiso 1 1 calc GR . . . .
C12 C 0.8523(3) 0.2864(4) 0.6028(3) 0.0583(7) Uani 1 1 d . . . . .
C13 C 0.8679(3) 0.4158(3) 0.7432(3) 0.0562(7) Uani 1 1 d . . . . .
C14 C 0.8079(3) 0.3906(4) 0.8472(3) 0.0635(7) Uani 1 1 d . . . . .
H14 H 0.7608 0.2903 0.8340 0.076 Uiso 1 1 calc R . . . .
C15 C 0.8201(4) 0.5181(4) 0.9703(4) 0.0732(9) Uani 1 1 d . . . . .
C16 C 0.8905(4) 0.6674(4) 0.9971(4) 0.0782(10) Uani 1 1 d . . . . .
H16 H 0.8962 0.7507 1.0820 0.094 Uiso 1 1 calc R . . . .
C17 C 0.9527(4) 0.6910(4) 0.8947(4) 0.0825(10) Uani 1 1 d . . . . .
H17 H 1.0032 0.7917 0.9109 0.099 Uiso 1 1 calc R . . . .
C18 C 0.9411(4) 0.5674(4) 0.7684(4) 0.0716(8) Uani 1 1 d . . . . .
H18 H 0.9825 0.5853 0.6995 0.086 Uiso 1 1 calc R . . . .
F1 F 0.7606(3) 0.4930(3) 1.0717(2) 0.1147(9) Uani 1 1 d . . . . .
N1 N 0.8679(3) 0.0834(3) 0.6658(2) 0.0537(6) Uani 1 1 d . . . . .
H1 H 0.939(3) 0.068(3) 0.642(3) 0.037(7) Uiso 1 1 d . . . . .
O1 O 0.8991(2) -0.0547(3) 0.7992(2) 0.0735(6) Uani 1 1 d . . . . .
O2 O 0.6804(2) 0.0130(3) 0.7858(2) 0.0725(6) Uani 1 1 d . . . . .
O3 O 0.8493(2) -0.0524(3) 0.3744(2) 0.0682(6) Uani 1 1 d . . . . .
O4 O 0.6480(2) -0.0011(3) 0.3458(2) 0.0703(6) Uani 1 1 d . . . . .
O5 O 0.8926(3) 0.3107(3) 0.5081(3) 0.0832(7) Uani 1 1 d . . . . .
S1 S 0.78764(8) -0.04139(9) 0.72078(7) 0.0582(2) Uani 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
C1 C2 1.386(4) . ?
C1 C6 1.374(4) . ?
C1 S1 1.762(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C4 C5 1.364(5) . ?
C4 C7 1.515(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C9 1.527(4) . ?
C8 C12 1.544(4) . ?
C8 N1 1.453(3) . ?
C9 O3 1.196(3) . ?
C9 O4 1.326(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.484(6) . ?
C10 O4 1.460(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.487(4) . ?
C12 O5 1.212(3) . ?
C13 C14 1.384(4) . ?
C13 C18 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C15 C16 1.361(5) . ?
C15 F1 1.356(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(5) . ?
C18 H18 0.9300 . ?
N1 H1 0.80(3) . ?
N1 S1 1.640(2) . ?
O1 S1 1.422(2) . ?
O2 S1 1.431(2) . ?

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
C2 C1 S1 119.3(2) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 S1 119.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 120.9(4) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.9(3) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8 108.8 . . ?
C9 C8 C12 108.4(2) . . ?
C12 C8 H8 108.8 . . ?
N1 C8 H8 108.8 . . ?
N1 C8 C9 112.4(2) . . ?
N1 C8 C12 109.4(2) . . ?
O3 C9 C8 123.8(2) . . ?
O3 C9 O4 125.6(3) . . ?
O4 C9 C8 110.6(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
O4 C10 H10A 109.7 . . ?
O4 C10 H10B 109.7 . . ?
O4 C10 C11 110.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 119.6(2) . . ?
O5 C12 C8 118.8(3) . . ?
O5 C12 C13 121.6(3) . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 C18 119.2(3) . . ?
C18 C13 C12 118.5(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 123.7(3) . . ?
F1 C15 C14 117.9(3) . . ?
F1 C15 C16 118.4(3) . . ?
C15 C16 H16 121.1 . . ?
C15 C16 C17 117.8(3) . . ?
C17 C16 H16 121.1 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C8 N1 H1 115.6(19) . . ?
C8 N1 S1 118.63(19) . . ?
S1 N1 H1 110.3(19) . . ?
C9 O4 C10 116.5(2) . . ?
N1 S1 C1 107.06(13) . . ?
O1 S1 C1 109.74(15) . . ?
O1 S1 N1 105.33(13) . . ?
O1 S1 O2 120.51(15) . . ?
O2 S1 C1 107.54(14) . . ?
O2 S1 N1 105.89(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.80(3) 2.18(3) 2.968(3) 167(3) 2_756

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
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C2 C1 S1 N1 82.9(3) . . . . ?
C2 C1 S1 O1 -30.9(3) . . . . ?
C2 C1 S1 O2 -163.6(2) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C2 C3 C4 C7 179.5(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C6 C1 S1 N1 -94.2(3) . . . . ?
C6 C1 S1 O1 152.0(3) . . . . ?
C6 C1 S1 O2 19.2(3) . . . . ?
C7 C4 C5 C6 -179.5(4) . . . . ?
C8 C9 O4 C10 173.3(3) . . . . ?
C8 C12 C13 C14 -7.0(4) . . . . ?
C8 C12 C13 C18 175.3(3) . . . . ?
C8 N1 S1 C1 60.3(2) . . . . ?
C8 N1 S1 O1 177.1(2) . . . . ?
C8 N1 S1 O2 -54.2(2) . . . . ?
C9 C8 C12 C13 174.0(2) . . . . ?
C9 C8 C12 O5 -5.4(4) . . . . ?
C9 C8 N1 S1 -91.1(3) . . . . ?
C11 C10 O4 C9 -81.9(4) . . . . ?
C12 C8 C9 O3 95.5(3) . . . . ?
C12 C8 C9 O4 -83.1(3) . . . . ?
C12 C8 N1 S1 148.3(2) . . . . ?
C12 C13 C14 C15 -175.8(3) . . . . ?
C12 C13 C18 C17 177.1(3) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C13 C14 C15 F1 179.7(3) . . . . ?
C14 C13 C18 C17 -0.6(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C16 C17 C18 C13 -1.0(6) . . . . ?
C18 C13 C14 C15 1.9(5) . . . . ?
F1 C15 C16 C17 178.7(3) . . . . ?
N1 C8 C9 O3 -25.6(4) . . . . ?
N1 C8 C9 O4 155.9(2) . . . . ?
N1 C8 C12 C13 -63.0(3) . . . . ?
N1 C8 C12 O5 117.5(3) . . . . ?
O3 C9 O4 C10 -5.3(5) . . . . ?
O5 C12 C13 C14 172.5(3) . . . . ?
O5 C12 C13 C18 -5.2(4) . . . . ?
S1 C1 C2 C3 -176.3(3) . . . . ?
S1 C1 C6 C5 176.3(3) . . . . ?

_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 2.381
_oxdiff_exptl_absorpt_empirical_full_min 0.784
