# Supplementary Information (SI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2245406'
loop_
_audit_author_name
_audit_author_address
'Nan '
;South China University of Technology
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2023-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 S'
_chemical_formula_sum            'C15 H16 N2 S'
_chemical_formula_weight         256.36
_chemical_melting_point          ?
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'
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.6219(2)
_cell_length_b                   13.9013(2)
_cell_length_c                   8.4102(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1358.75(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8120
_cell_measurement_theta_min      4.9870
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4973
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.966
_diffrn_reflns_theta_min         4.960
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  37.00   0.50    0.50    --   -1.00   2.00 -67.00   50
  2  ω    -57.00 -32.00   0.50    0.50    --    5.00  -2.00 127.00   50
  3  ω    -81.00 -55.00   0.50    0.50    -- -100.10   2.00 -67.00   52
  4  ω   -162.00-137.00   0.50    0.50    -- -100.10  -2.00 127.00   50
  5  ω    -16.00   9.00   0.50    0.50    --   -1.00 -72.00  60.00   50
  6  ω    -73.00 -44.00   0.50    0.50    --   -1.00 -72.00  60.00   58
  7  ω    -58.00  12.00   0.50    0.50    --    1.00 -57.00 -30.00  140
  8  ω    -85.00 -60.00   0.50    0.50    --    1.00 -57.00 -30.00   50
  9  ω   -188.00-141.00   0.50    0.50    -- -100.10 -19.00 -30.00   94
 10  ω   -132.00 -92.00   0.50    0.50    -- -100.10 -19.00 -30.00   80
 11  ω    -98.00 -58.00   0.50    0.50    -- -100.10  72.00-180.00   80
 12  ω   -105.00 -12.00   0.50    0.50    -- -100.10  72.00  90.00  186
 13  ω   -114.00 -33.00   0.50    0.50    -- -100.10  19.00 150.00  162
 14  ω   -112.00 -87.00   0.50    0.50    -- -100.10  72.00 150.00   50
 15  ω   -114.00 -49.00   0.50    0.50    -- -100.10  72.00  30.00  130
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0292684000
_diffrn_orient_matrix_UB_12      -0.1080270000
_diffrn_orient_matrix_UB_13      0.0051924000
_diffrn_orient_matrix_UB_21      0.1291553000
_diffrn_orient_matrix_UB_22      -0.0244485000
_diffrn_orient_matrix_UB_23      0.0021824000
_diffrn_orient_matrix_UB_31      -0.0005590000
_diffrn_orient_matrix_UB_32      0.0035099000
_diffrn_orient_matrix_UB_33      0.1832774000
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1268
_reflns_number_total             1331
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.058
_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)+(0.0521P)²+0.5922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.500000 0.45921(3) 0.250000 0.02094(17) Uani 1 2 d S T P . .
N1 N 0.48797(9) 0.63020(8) 0.38714(14) 0.0224(3) Uani 1 1 d . . . . .
H1 H 0.512787 0.602534 0.471932 0.027 Uiso 1 1 calc R U . . .
C1 C 0.28323(14) 1.00178(10) 0.4780(2) 0.0374(4) Uani 1 1 d . . . . .
H1A H 0.275710 1.033549 0.377197 0.056 Uiso 1 1 calc R U . . .
H1B H 0.331314 1.039517 0.546738 0.056 Uiso 1 1 calc R U . . .
H1C H 0.208607 0.994489 0.525448 0.056 Uiso 1 1 calc R U . . .
C2 C 0.33679(11) 0.90394(9) 0.45388(17) 0.0262(3) Uani 1 1 d . . . . .
C3 C 0.43103(13) 0.87458(10) 0.54252(17) 0.0313(3) Uani 1 1 d . . . . .
H3 H 0.460877 0.915737 0.619323 0.038 Uiso 1 1 calc R U . . .
C4 C 0.48219(12) 0.78503(10) 0.51955(18) 0.0286(3) Uani 1 1 d . . . . .
H4 H 0.545485 0.766827 0.580159 0.034 Uiso 1 1 calc R U . . .
C5 C 0.43795(11) 0.72340(8) 0.40570(15) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.34229(11) 0.75060(9) 0.31706(16) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.311611 0.708884 0.241726 0.030 Uiso 1 1 calc R U . . .
C7 C 0.29295(11) 0.84002(9) 0.34147(17) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.229161 0.857841 0.281551 0.032 Uiso 1 1 calc R U . . .
C8 C 0.500000 0.58152(13) 0.250000 0.0192(4) Uani 1 2 d S T P . .


_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 C8 1.7003(18) . ?
N1 H1 0.8600 . ?
N1 C5 1.4286(15) . ?
N1 C8 1.3445(14) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.5094(18) . ?
C2 C3 1.386(2) . ?
C2 C7 1.3939(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3930(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.3839(18) . ?
C5 C6 1.3909(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.3843(18) . ?
C7 H7 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
C5 N1 H1 116.8 . . ?
C8 N1 H1 116.8 . . ?
C8 N1 C5 126.33(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.25(13) . . ?
C3 C2 C7 117.76(12) . . ?
C7 C2 C1 120.99(13) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.72(13) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.38(13) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 N1 119.07(12) . . ?
C4 C5 C6 119.97(12) . . ?
C6 C5 N1 120.87(11) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.72(12) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.44(12) . . ?
C6 C7 H7 119.3 . . ?
N1 C8 S1 120.22(8) 3_655 . ?
N1 C8 S1 120.22(8) . . ?
N1 C8 N1 119.57(16) . 3_655 ?

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
N1 C5 C6 C7 177.65(12) . . . . ?
C1 C2 C3 C4 -179.02(14) . . . . ?
C1 C2 C7 C6 179.20(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C3 C4 C5 N1 -177.53(12) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C5 N1 C8 S1 -150.99(9) . . . . ?
C5 N1 C8 N1 29.02(9) . . . 3_655 ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C7 C2 C3 C4 1.0(2) . . . . ?
C8 N1 C5 C4 -145.26(12) . . . . ?
C8 N1 C5 C6 38.14(18) . . . . ?

_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2407300'
loop_
_audit_author_name
_audit_author_address
'Nan '
;South China University of Technology
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2024-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O4 S3, C2 H6 O S'
_chemical_formula_sum            'C17 H22 N2 O5 S4'
_chemical_formula_weight         462.60
_chemical_melting_point          ?
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   8.74660(10)
_cell_length_b                   11.0403(2)
_cell_length_c                   22.1225(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.9720(10)
_cell_angle_gamma                90
_cell_volume                     2131.13(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3562
_cell_measurement_temperature    301.31(10)
_cell_measurement_theta_max      73.2850
_cell_measurement_theta_min      4.4980
_shelx_estimated_absorpt_T_max   0.669
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    4.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5086
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.653
_diffrn_reflns_theta_min         4.006
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -46.00   0.50    0.50    --    0.00 -19.00  30.00   86
  2  ω    -44.00  13.00   0.50    0.50    --    0.00 -37.00  60.00  114
  3  ω      8.00  56.00   0.50    0.50    --    5.00  57.00 -90.00   96
  4  ω   -107.00 -18.00   0.50    0.50    --  -98.80  57.00 150.00  178
  5  ω   -100.00 -49.00   0.50    0.50    --  -98.80  72.00-180.00  102
  6  ω    -38.00 -12.00   0.50    0.50    --  -98.80  72.00-180.00   52
  7  ω   -175.00 -85.00   0.50    0.50    --  -98.80 -37.00 -60.00  180
  8  ω    -89.00 -28.00   0.50    0.50    --  -98.80  72.00 -90.00  122
  9  ω   -100.00 -74.00   0.50    0.50    --  -98.80  72.00 150.00   52
 10  ω    -43.00 -18.00   0.50    0.50    --  -98.80  72.00 150.00   50
 11  ω   -109.00 -11.00   0.50    0.50    --  -98.80  72.00-120.00  196
 12  ω   -180.00-155.00   0.50    0.50    --  -98.80 -19.00-180.00   50
 13  ω   -176.00 -88.00   0.50    0.50    --  -98.80 -37.00  30.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0214432000
_diffrn_orient_matrix_UB_12      -0.1325477000
_diffrn_orient_matrix_UB_13      -0.0206798000
_diffrn_orient_matrix_UB_21      -0.0028085000
_diffrn_orient_matrix_UB_22      0.0408146000
_diffrn_orient_matrix_UB_23      -0.0666626000
_diffrn_orient_matrix_UB_31      0.1751947000
_diffrn_orient_matrix_UB_32      -0.0155827000
_diffrn_orient_matrix_UB_33      0.0012928000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1873
_reflns_number_total             2015
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00075(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.096
_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)+(0.0706P)²+1.1817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1191
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S01-O005 \\sim S003-O007
 with sigma of 0.02
 S01-C00F \\sim S003-C1 \\sim S003-C00G
 with sigma of 0.02
3. Others
 Fixed Sof: S003(0.5) O007(0.5) C00G(0.5) H00H(0.5) H00I(0.5) H00J(0.5)
 C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N006(H006), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E)
4.b Idealised Me refined as rotating group:
 C00F(H00B,H00F,H00G), C00G(H00H,H00I,H00J), C1(H1A,H1B,H1C)
;
_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
S01 S 0.52879(5) 0.60461(4) 0.80247(2) 0.0461(2) Uani 1 1 d D . . . .
S02 S 0.250000 0.74162(7) 0.500000 0.0745(3) Uani 1 2 d S T P . .
S003 S 0.17915(14) 0.15761(10) 0.48076(5) 0.0584(3) Uani 0.5 1 d D . P A -1
O004 O 0.66285(17) 0.68021(15) 0.80539(7) 0.0573(4) Uani 1 1 d . . . . .
O005 O 0.5401(2) 0.48772(15) 0.83135(7) 0.0629(4) Uani 1 1 d D . . . .
N006 N 0.3022(2) 0.52039(16) 0.54713(8) 0.0584(5) Uani 1 1 d . . . . .
H006 H 0.300614 0.444064 0.539355 0.070 Uiso 1 1 calc R U . . .
O007 O 0.225(3) 0.2828(3) 0.4981(17) 0.088(5) Uani 0.5 1 d D . P A -1
C008 C 0.4652(2) 0.58349(18) 0.72597(8) 0.0435(4) Uani 1 1 d . . . . .
C009 C 0.3586(2) 0.54934(18) 0.60648(8) 0.0466(4) Uani 1 1 d . . . . .
C00A C 0.3896(3) 0.47704(19) 0.70886(10) 0.0560(5) Uani 1 1 d . . . . .
H00A H 0.373714 0.417461 0.737481 0.067 Uiso 1 1 calc R U . . .
C00B C 0.250000 0.5909(3) 0.500000 0.0471(6) Uani 1 2 d S T P . .
C00C C 0.4886(3) 0.67198(19) 0.68346(9) 0.0533(5) Uani 1 1 d . . . . .
H00C H 0.540399 0.742737 0.695034 0.064 Uiso 1 1 calc R U . . .
C00D C 0.3385(3) 0.4604(2) 0.64954(10) 0.0588(6) Uani 1 1 d . . . . .
H00D H 0.289586 0.388486 0.637930 0.071 Uiso 1 1 calc R U . . .
C00E C 0.4350(3) 0.65555(19) 0.62356(9) 0.0545(5) Uani 1 1 d . . . . .
H00E H 0.450182 0.715320 0.594960 0.065 Uiso 1 1 calc R U . . .
C00F C 0.3794(3) 0.6851(3) 0.83315(11) 0.0663(6) Uani 1 1 d D . . . .
H00B H 0.405771 0.701119 0.875242 0.099 Uiso 1 1 calc R U . . .
H00F H 0.287107 0.637939 0.829133 0.099 Uiso 1 1 calc R U . . .
H00G H 0.363756 0.760355 0.811857 0.099 Uiso 1 1 calc R U . . .
C00G C 0.331(2) 0.0795(17) 0.4496(8) 0.082(5) Uani 0.5 1 d D . P A -1
H00H H 0.345586 0.111000 0.410044 0.123 Uiso 0.5 1 calc R U P A -1
H00I H 0.306022 -0.005148 0.446620 0.123 Uiso 0.5 1 calc R U P A -1
H00J H 0.422732 0.089979 0.475289 0.123 Uiso 0.5 1 calc R U P A -1
C1 C 0.187(2) 0.0839(19) 0.5523(6) 0.094(6) Uani 0.5 1 d D . P A -1
H1A H 0.290848 0.082471 0.569269 0.141 Uiso 0.5 1 calc R U P A -1
H1B H 0.149817 0.002445 0.547176 0.141 Uiso 0.5 1 calc R U P A -1
H1C H 0.124118 0.126979 0.578973 0.141 Uiso 0.5 1 calc R U P A -1


_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
S01 O004 1.4370(16) . ?
S01 O005 1.4404(16) . ?
S01 C008 1.7600(19) . ?
S01 C00F 1.755(2) . ?
S02 C00B 1.664(3) . ?
S003 O007 1.481(10) . ?
S003 C00G 1.760(12) . ?
S003 C1 1.776(10) . ?
N006 H006 0.8600 . ?
N006 C009 1.407(2) . ?
N006 C00B 1.355(2) . ?
C008 C00A 1.388(3) . ?
C008 C00C 1.381(3) . ?
C009 C00D 1.387(3) . ?
C009 C00E 1.389(3) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.369(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.387(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00B 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
O004 S01 O005 118.02(10) . . ?
O004 S01 C008 108.83(9) . . ?
O004 S01 C00F 108.38(12) . . ?
O005 S01 C008 108.38(10) . . ?
O005 S01 C00F 108.19(13) . . ?
C00F S01 C008 104.18(11) . . ?
O007 S003 C00G 111.2(14) . . ?
O007 S003 C1 101.8(16) . . ?
C00G S003 C1 98.1(7) . . ?
C009 N006 H006 114.1 . . ?
C00B N006 H006 114.1 . . ?
C00B N006 C009 131.72(19) . . ?
C00A C008 S01 119.16(15) . . ?
C00C C008 S01 120.61(15) . . ?
C00C C008 C00A 120.23(18) . . ?
C00D C009 N006 115.29(18) . . ?
C00D C009 C00E 119.46(19) . . ?
C00E C009 N006 125.20(18) . . ?
C008 C00A H00A 120.3 . . ?
C00D C00A C008 119.49(19) . . ?
C00D C00A H00A 120.3 . . ?
N006 C00B S02 125.06(13) . . ?
N006 C00B S02 125.06(13) 2_556 . ?
N006 C00B N006 109.9(3) 2_556 . ?
C008 C00C H00C 119.9 . . ?
C008 C00C C00E 120.13(18) . . ?
C00E C00C H00C 119.9 . . ?
C009 C00D H00D 119.5 . . ?
C00A C00D C009 121.01(19) . . ?
C00A C00D H00D 119.5 . . ?
C009 C00E H00E 120.2 . . ?
C00C C00E C009 119.66(18) . . ?
C00C C00E H00E 120.2 . . ?
S01 C00F H00B 109.5 . . ?
S01 C00F H00F 109.5 . . ?
S01 C00F H00G 109.5 . . ?
H00B C00F H00F 109.5 . . ?
H00B C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
S003 C00G H00H 109.5 . . ?
S003 C00G H00I 109.5 . . ?
S003 C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 109.5 . . ?
S003 C1 H1A 109.5 . . ?
S003 C1 H1B 109.5 . . ?
S003 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
S01 C008 C00A C00D 179.39(19) . . . . ?
S01 C008 C00C C00E -178.56(17) . . . . ?
O004 S01 C008 C00A 150.38(18) . . . . ?
O004 S01 C008 C00C -30.3(2) . . . . ?
O005 S01 C008 C00A 20.9(2) . . . . ?
O005 S01 C008 C00C -159.80(18) . . . . ?
N006 C009 C00D C00A 179.4(2) . . . . ?
N006 C009 C00E C00C -178.3(2) . . . . ?
C008 C00A C00D C009 -1.2(4) . . . . ?
C008 C00C C00E C009 -0.4(4) . . . . ?
C009 N006 C00B S02 4.2(3) . . . . ?
C009 N006 C00B N006 -175.8(3) . . . 2_556 ?
C00A C008 C00C C00E 0.8(4) . . . . ?
C00B N006 C009 C00D 152.5(2) . . . . ?
C00B N006 C009 C00E -29.9(4) . . . . ?
C00C C008 C00A C00D 0.1(4) . . . . ?
C00D C009 C00E C00C -0.8(4) . . . . ?
C00E C009 C00D C00A 1.6(4) . . . . ?
C00F S01 C008 C00A -94.2(2) . . . . ?
C00F S01 C008 C00C 85.2(2) . . . . ?

_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 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.726
####################################################################### 
# 
# 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_1_1
_database_code_depnum_ccdc_archive 'CCDC 2407294'
loop_
_audit_author_name
_audit_author_address
'Nan '
;South China University of Technology
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2024-09-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 F6 N2 S'
_chemical_formula_sum            'C15 H10 F6 N2 S'
_chemical_formula_weight         364.31
_chemical_melting_point          ?
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'
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                   14.2700(3)
_cell_length_b                   7.5957(2)
_cell_length_c                   14.4949(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.715(2)
_cell_angle_gamma                90
_cell_volume                     1532.58(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5159
_cell_measurement_temperature    302.36(10)
_cell_measurement_theta_max      73.2650
_cell_measurement_theta_min      6.2850
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    2.521
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_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  0.0203
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9056
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.583
_diffrn_reflns_theta_min         3.175
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.36(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  43.00   0.50    0.50    --    5.00   8.00 -82.00   50
  2  ω    -57.00 -32.00   0.50    0.50    --    5.00  -8.00 105.00   50
  3  ω    -98.00 -60.00   0.50    0.50    --  -98.80   8.00 -82.00   76
  4  ω    -45.00  13.00   0.50    0.50    --    0.00 -37.00-120.00  116
  5  ω    -46.00   9.00   0.50    0.50    --    0.00 -57.00-150.00  110
  6  ω    -79.00 -53.00   0.50    0.50    --    0.00 -37.00-120.00   52
  7  ω     17.00  42.00   0.50    0.50    --    5.00  72.00  60.00   50
  8  ω    -46.00  14.00   0.50    0.50    --    5.00 -72.00 -30.00  120
  9  ω   -113.00  -9.00   0.50    0.50    --  -98.80  57.00  30.00  208
 10  ω   -130.00-104.00   0.50    0.50    --  -98.80 -19.00 -60.00   52
 11  ω   -109.00 -68.00   0.50    0.50    --  -98.80  19.00 120.00   82
 12  ω    -64.00 -23.00   0.50    0.50    --  -98.80  57.00 -60.00   82
 13  ω   -106.00 -81.00   0.50    0.50    --  -98.80  57.00 -60.00   50
 14  ω   -110.00 -25.00   0.50    0.50    --  -98.80  72.00  60.00  170
 15  ω   -188.00-111.00   0.50    0.50    --  -98.80 -19.00-120.00  154
 16  ω    -58.00  -9.00   0.50    0.50    --  -98.80  19.00 120.00   98
 17  ω   -104.00 -12.00   0.50    0.50    --  -98.80  19.00  30.00  184
 18  ω   -109.00 -83.00   0.50    0.50    --  -98.80  72.00   0.00   52
 19  ω    -98.00 -22.00   0.50    0.50    --  -98.80  72.00 120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0163944000
_diffrn_orient_matrix_UB_12      0.0219031000
_diffrn_orient_matrix_UB_13      0.1009160000
_diffrn_orient_matrix_UB_21      0.1093783000
_diffrn_orient_matrix_UB_22      0.0088903000
_diffrn_orient_matrix_UB_23      0.0390052000
_diffrn_orient_matrix_UB_31      -0.0029695000
_diffrn_orient_matrix_UB_32      0.2015183000
_diffrn_orient_matrix_UB_33      -0.0127171000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2675
_reflns_number_total             2973
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.089
_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)+(0.0944P)²+0.9685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1795
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14)
;
_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 0.42044(5) 0.35266(9) 0.61652(4) 0.0528(3) Uani 1 1 d . . . . .
F1 F 0.92243(16) 0.2944(5) 0.54049(19) 0.1242(11) Uani 1 1 d . . . . .
F2 F 0.8427(2) 0.1648(4) 0.4210(2) 0.1306(12) Uani 1 1 d . . . . .
F3 F 0.8196(2) 0.4308(4) 0.4396(2) 0.1218(10) Uani 1 1 d . . . . .
F4 F 0.0170(3) 0.3933(7) 0.8008(4) 0.234(3) Uani 1 1 d . . . . .
F5 F 0.0807(2) 0.3371(6) 0.9363(3) 0.1750(19) Uani 1 1 d . . . . .
F6 F 0.0131(2) 0.1477(4) 0.8504(3) 0.1648(17) Uani 1 1 d . . . . .
N1 N 0.54742(17) 0.0997(3) 0.68340(17) 0.0596(6) Uani 1 1 d . . . . .
H1 H 0.561458 0.008251 0.718710 0.071 Uiso 1 1 calc R U . . .
N2 N 0.41479(16) 0.0997(3) 0.74350(16) 0.0582(6) Uani 1 1 d . . . . .
H2 H 0.441024 0.006887 0.771993 0.070 Uiso 1 1 calc R U . . .
C1 C 0.8364(2) 0.2812(5) 0.4861(2) 0.0725(9) Uani 1 1 d . . . . .
C2 C 0.7603(2) 0.2364(4) 0.5384(2) 0.0581(7) Uani 1 1 d . . . . .
C3 C 0.6666(2) 0.2161(4) 0.4888(2) 0.0623(7) Uani 1 1 d . . . . .
H3 H 0.651768 0.231366 0.423551 0.075 Uiso 1 1 calc R U . . .
C4 C 0.5945(2) 0.1734(4) 0.5348(2) 0.0599(7) Uani 1 1 d . . . . .
H4 H 0.531620 0.158714 0.500924 0.072 Uiso 1 1 calc R U . . .
C5 C 0.6172(2) 0.1526(3) 0.63249(19) 0.0530(7) Uani 1 1 d . . . . .
C6 C 0.7104(2) 0.1723(5) 0.6813(2) 0.0659(8) Uani 1 1 d . . . . .
H6 H 0.725674 0.156445 0.746493 0.079 Uiso 1 1 calc R U . . .
C7 C 0.7817(2) 0.2151(5) 0.6350(2) 0.0705(9) Uani 1 1 d . . . . .
H7 H 0.844517 0.229804 0.669131 0.085 Uiso 1 1 calc R U . . .
C8 C 0.46183(18) 0.1756(4) 0.68306(17) 0.0489(6) Uani 1 1 d . . . . .
C9 C 0.32724(19) 0.1536(4) 0.76616(18) 0.0518(6) Uani 1 1 d . . . . .
C10 C 0.2441(2) 0.1837(5) 0.6987(2) 0.0681(8) Uani 1 1 d . . . . .
H10 H 0.244605 0.175277 0.634801 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1604(2) 0.2265(5) 0.7262(2) 0.0723(9) Uani 1 1 d . . . . .
H11 H 0.104582 0.247444 0.680690 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1590(2) 0.2383(4) 0.8210(2) 0.0617(7) Uani 1 1 d . . . . .
C13 C 0.2421(2) 0.2068(5) 0.8879(2) 0.0655(8) Uani 1 1 d . . . . .
H13 H 0.241705 0.214565 0.951864 0.079 Uiso 1 1 calc R U . . .
C14 C 0.3256(2) 0.1641(4) 0.86074(19) 0.0600(7) Uani 1 1 d . . . . .
H14 H 0.381261 0.142275 0.906353 0.072 Uiso 1 1 calc R U . . .
C15 C 0.0683(2) 0.2813(6) 0.8513(3) 0.0789(10) 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
S1 C8 1.685(3) . ?
F1 C1 1.309(4) . ?
F2 C1 1.310(4) . ?
F3 C1 1.316(4) . ?
F4 C15 1.249(5) . ?
F5 C15 1.279(5) . ?
F6 C15 1.282(5) . ?
N1 H1 0.8600 . ?
N1 C5 1.422(3) . ?
N1 C8 1.350(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.345(3) . ?
N2 C9 1.420(3) . ?
C1 C2 1.494(4) . ?
C2 C3 1.381(4) . ?
C2 C7 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.370(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(4) . ?
C7 H7 0.9300 . ?
C9 C10 1.380(4) . ?
C9 C14 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(4) . ?
C12 C13 1.378(4) . ?
C12 C15 1.491(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 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
C5 N1 H1 116.0 . . ?
C8 N1 H1 116.0 . . ?
C8 N1 C5 127.9(2) . . ?
C8 N2 H2 115.9 . . ?
C8 N2 C9 128.2(2) . . ?
C9 N2 H2 115.9 . . ?
F1 C1 F2 106.4(3) . . ?
F1 C1 F3 106.5(3) . . ?
F1 C1 C2 113.7(3) . . ?
F2 C1 F3 104.4(3) . . ?
F2 C1 C2 112.5(3) . . ?
F3 C1 C2 112.7(3) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 121.4(3) . . ?
C7 C2 C3 119.3(3) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 N1 121.8(3) . . ?
C6 C5 N1 118.3(2) . . ?
C6 C5 C4 119.7(3) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
N1 C8 S1 123.1(2) . . ?
N2 C8 S1 123.6(2) . . ?
N2 C8 N1 113.3(2) . . ?
C10 C9 N2 123.1(2) . . ?
C14 C9 N2 117.1(2) . . ?
C14 C9 C10 119.6(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C15 120.7(3) . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 C15 120.0(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
F4 C15 F5 106.1(5) . . ?
F4 C15 F6 104.7(4) . . ?
F4 C15 C12 114.3(3) . . ?
F5 C15 F6 103.1(4) . . ?
F5 C15 C12 114.2(3) . . ?
F6 C15 C12 113.2(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
F1 C1 C2 C3 -179.0(3) . . . . ?
F1 C1 C2 C7 1.1(5) . . . . ?
F2 C1 C2 C3 -58.0(4) . . . . ?
F2 C1 C2 C7 122.1(4) . . . . ?
F3 C1 C2 C3 59.7(4) . . . . ?
F3 C1 C2 C7 -120.2(4) . . . . ?
N1 C5 C6 C7 176.9(3) . . . . ?
N2 C9 C10 C11 176.5(3) . . . . ?
N2 C9 C14 C13 -176.8(3) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C7 C6 -179.4(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C2 C7 C6 0.7(5) . . . . ?
C3 C4 C5 N1 -176.6(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C7 1.0(5) . . . . ?
C5 N1 C8 S1 1.5(4) . . . . ?
C5 N1 C8 N2 -176.2(3) . . . . ?
C5 C6 C7 C2 -1.0(5) . . . . ?
C7 C2 C3 C4 -0.6(5) . . . . ?
C8 N1 C5 C4 -55.0(4) . . . . ?
C8 N1 C5 C6 129.2(3) . . . . ?
C8 N2 C9 C10 53.0(4) . . . . ?
C8 N2 C9 C14 -131.2(3) . . . . ?
C9 N2 C8 S1 -2.9(4) . . . . ?
C9 N2 C8 N1 174.9(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C10 C11 C12 C15 -178.9(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C11 C12 C15 F4 -38.5(6) . . . . ?
C11 C12 C15 F5 -161.0(4) . . . . ?
C11 C12 C15 F6 81.3(5) . . . . ?
C12 C13 C14 C9 0.5(5) . . . . ?
C13 C12 C15 F4 142.6(5) . . . . ?
C13 C12 C15 F5 20.1(6) . . . . ?
C13 C12 C15 F6 -97.5(5) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C15 C12 C13 C14 178.9(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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2407295'
loop_
_audit_author_name
_audit_author_address
'Nan '
;South China University of Technology
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2024-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N4 S'
_chemical_formula_sum            'C15 H10 N4 S'
_chemical_formula_weight         278.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   24.3010(9)
_cell_length_b                   13.2694(4)
_cell_length_c                   8.6371(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2785.12(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    300.55(10)
_cell_measurement_theta_max      72.8790
_cell_measurement_theta_min      3.6440
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    2.016
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.12
_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  0.0125
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2627
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.486
_diffrn_reflns_theta_min         6.380
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -37.00   0.50    0.50    --    0.00 -70.00 -68.00   50
  2  ω     42.00  92.00   0.50    0.50    --    5.00  59.00-151.00  100
  3  ω    -85.00 -60.00   0.50    0.50    --  -98.80  70.00  62.00   50
  4  ω    -85.00 -60.00   0.50    0.50    --  -98.80  59.00-151.00   50
  5  ω   -161.00-136.00   0.50    0.50    --  -98.80 -70.00 -68.00   50
  6  ω   -154.00-128.00   0.50    0.50    --  -98.80 -59.00  68.00   52
  7  ω    -26.00   8.00   0.50    0.50    --    0.00 -19.00  90.00   68
  8  ω    -88.00 -34.00   0.50    0.50    --    0.00 -19.00  90.00  108
  9  ω   -188.00 -86.00   0.50    0.50    --  -98.80 -72.00-180.00  204
 10  ω   -172.00 -85.00   0.50    0.50    --  -98.80 -57.00  90.00  174
 11  ω   -113.00 -10.00   0.50    0.50    --  -98.80  57.00 -60.00  206
 12  ω   -159.00-134.00   0.50    0.50    --  -98.80 -19.00 -90.00   50
 13  ω    -62.00 -37.00   0.50    0.50    --  -98.80  19.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356637000
_diffrn_orient_matrix_UB_12      -0.0262602000
_diffrn_orient_matrix_UB_13      0.1417017000
_diffrn_orient_matrix_UB_21      -0.0251847000
_diffrn_orient_matrix_UB_22      -0.1064419000
_diffrn_orient_matrix_UB_23      0.0035930000
_diffrn_orient_matrix_UB_31      0.0459927000
_diffrn_orient_matrix_UB_32      -0.0381452000
_diffrn_orient_matrix_UB_33      -0.1082314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.636
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                1177
_reflns_number_total             1188
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(13)
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1188
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.090
_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)+(0.1205P)²+5.3069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.1902
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 H2-H2_$1
 2.1 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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 0.500000 0.500000 0.6406(3) 0.0777(8) Uani 1 2 d S T P . .
N1 N 0.3819(2) 0.3149(5) 0.3958(9) 0.0872(17) Uani 1 1 d . . . . .
N2 N 0.51355(16) 0.41821(11) 0.3595(5) 0.0510(10) Uani 1 1 d . . . . .
H2 H 0.514616 0.425717 0.260679 0.061 Uiso 1 1 calc DR U . . .
C1 C 0.4265(2) 0.2913(4) 0.4189(7) 0.0633(14) Uani 1 1 d . . . . .
C2 C 0.4819(2) 0.2614(4) 0.4505(7) 0.0553(12) Uani 1 1 d . . . . .
C3 C 0.4946(2) 0.1659(5) 0.5026(8) 0.0687(17) Uani 1 1 d . . . . .
H3 H 0.466421 0.119802 0.520494 0.082 Uiso 1 1 calc R U . . .
C4 C 0.5485(3) 0.1379(5) 0.5286(9) 0.0713(16) Uani 1 1 d . . . . .
H4 H 0.556784 0.074117 0.566777 0.086 Uiso 1 1 calc R U . . .
C5 C 0.5901(2) 0.2065(5) 0.4966(10) 0.0779(18) Uani 1 1 d . . . . .
H5 H 0.626601 0.187197 0.509715 0.093 Uiso 1 1 calc R U . . .
C6 C 0.5785(2) 0.3025(5) 0.4460(8) 0.0704(15) Uani 1 1 d . . . . .
H6 H 0.606676 0.348455 0.428152 0.084 Uiso 1 1 calc R U . . .
C7 C 0.5247(2) 0.3289(4) 0.4226(6) 0.0544(12) Uani 1 1 d . . . . .
C8 C 0.500000 0.500000 0.4554(10) 0.0521(16) Uani 1 2 d S T P . .


_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 C8 1.600(8) . ?
N1 C1 1.146(8) . ?
N2 H2 0.8600 . ?
N2 C7 1.332(5) . ?
N2 C8 1.404(6) . ?
C1 C2 1.428(7) . ?
C2 C3 1.381(8) . ?
C2 C7 1.395(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(8) . ?

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
C7 N2 H2 120.2 . . ?
C7 N2 C8 119.6(5) . . ?
C8 N2 H2 120.2 . . ?
N1 C1 C2 179.0(7) . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 C7 118.6(5) . . ?
C7 C2 C1 119.5(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.7(5) . . ?
C7 C6 H6 120.6 . . ?
N2 C7 C2 119.3(5) . . ?
N2 C7 C6 118.9(5) . . ?
C6 C7 C2 121.5(5) . . ?
N2 C8 S1 126.1(3) . . ?
N2 C8 S1 126.1(3) 2_665 . ?
N2 C8 N2 107.8(6) 2_665 . ?

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 178.3(7) . . . . ?
C1 C2 C7 N2 -3.4(8) . . . . ?
C1 C2 C7 C6 -177.7(6) . . . . ?
C2 C3 C4 C5 -2.0(11) . . . . ?
C3 C2 C7 N2 174.2(5) . . . . ?
C3 C2 C7 C6 -0.2(9) . . . . ?
C3 C4 C5 C6 2.7(11) . . . . ?
C4 C5 C6 C7 -2.0(11) . . . . ?
C5 C6 C7 N2 -173.6(6) . . . . ?
C5 C6 C7 C2 0.8(9) . . . . ?
C7 N2 C8 S1 4.1(5) . . . . ?
C7 N2 C8 N2 -175.9(5) . . . 2_665 ?
C7 C2 C3 C4 0.8(10) . . . . ?
C8 N2 C7 C2 88.3(6) . . . . ?
C8 N2 C7 C6 -97.2(6) . . . . ?

_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2407296'
loop_
_audit_author_name
_audit_author_address
'Nan '
;South China University of Technology
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2024-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N4 O4 S, C4 H8 O'
_chemical_formula_sum            'C17 H18 N4 O5 S'
_chemical_formula_weight         390.41
_chemical_melting_point          ?
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                   6.9039(2)
_cell_length_b                   10.6650(3)
_cell_length_c                   12.8313(6)
_cell_angle_alpha                69.245(4)
_cell_angle_beta                 89.785(3)
_cell_angle_gamma                83.280(2)
_cell_volume                     876.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5825
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6830
_cell_measurement_theta_min      4.4570
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7774
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.250
_diffrn_reflns_theta_min         3.687
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  26.00   0.50    0.50    --    1.00  72.00  30.00   64
  2  ω    -13.00  64.00   0.50    0.50    --    1.00  72.00 -60.00  154
  3  ω    -13.00  72.00   0.50    0.50    --    1.00  19.00-120.00  170
  4  ω    -84.00 -10.00   0.50    0.50    --    1.00 -57.00  90.00  148
  5  ω   -105.00 -56.00   0.50    0.50    -- -100.10  72.00 -90.00   98
  6  ω   -113.00 -12.00   0.50    0.50    -- -100.10  72.00 120.00  202
  7  ω   -114.00 -18.00   0.50    0.50    -- -100.10  19.00   0.00  192
  8  ω   -114.00 -56.00   0.50    0.50    -- -100.10  72.00   0.00  116
  9  ω    -52.00 -12.00   0.50    0.50    -- -100.10  72.00 -30.00   80
 10  ω   -107.00 -41.00   0.50    0.50    -- -100.10  72.00-150.00  132
 11  ω    -70.00 -31.00   0.50    0.50    -- -100.10  72.00  60.00   78
 12  ω   -178.00-145.00   0.50    0.50    -- -100.10 -19.00-180.00   66
 13  ω   -115.00 -88.00   0.50    0.50    -- -100.10 -19.00-180.00   54
 14  ω   -101.00 -49.00   0.50    0.50    -- -100.10  72.00 -60.00  104
 15  ω    -91.00 -22.00   0.50    0.50    -- -100.10  57.00 -90.00  138
 16  ω   -108.00 -83.00   0.50    0.50    -- -100.10  72.00 150.00   50
 17  ω   -188.00 -88.00   0.50    0.50    -- -100.10 -19.00 -60.00  200
 18  ω   -189.00 -91.00   0.50    0.50    -- -100.10 -19.00  30.00  196
 19  ω   -110.00 -57.00   0.50    0.50    -- -100.10  57.00-150.00  106
 20  ω   -103.00 -78.00   0.50    0.50    -- -100.10  72.00-180.00   50
 21  ω   -106.00 -80.00   0.50    0.50    -- -100.10  72.00  90.00   52
 22  ω   -110.00 -15.00   0.50    0.50    -- -100.10  57.00  60.00  190
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3145
_reflns_number_total             3349
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.078
_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)+(0.0607P)²+0.2580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 S1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C2(H2A), C3(H3A), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12),
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.18776(5) 0.69429(3) 0.45657(3) 0.03171(13) Uani 1 1 d . U . . .
O1 O 0.16116(19) 0.74884(12) -0.17450(9) 0.0446(3) Uani 1 1 d . . . . .
O2 O 0.12914(19) 0.93985(11) -0.14830(10) 0.0432(3) Uani 1 1 d . . . . .
O3 O 0.3660(2) 0.32153(12) 1.04546(10) 0.0478(3) Uani 1 1 d . . . . .
O4 O 0.3746(2) 0.11813(12) 1.04780(10) 0.0519(3) Uani 1 1 d . . . . .
N1 N 0.14708(19) 0.81574(13) -0.11314(11) 0.0331(3) Uani 1 1 d . . . . .
N2 N 0.20249(17) 0.51897(11) 0.34764(10) 0.0268(3) Uani 1 1 d . . . . .
H2 H 0.202246 0.432886 0.357998 0.032 Uiso 1 1 calc R U . . .
N3 N 0.27840(17) 0.42311(11) 0.53040(10) 0.0265(3) Uani 1 1 d . . . . .
H3 H 0.305396 0.354009 0.508253 0.032 Uiso 1 1 calc R U . . .
N4 N 0.36190(18) 0.24053(13) 0.99769(10) 0.0325(3) Uani 1 1 d . . . . .
C1 C 0.1538(2) 0.74343(14) 0.00738(12) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.1580(2) 0.81395(14) 0.07927(12) 0.0301(3) Uani 1 1 d . . . . .
H2A H 0.152479 0.909601 0.050447 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1704(2) 0.74444(14) 0.19360(12) 0.0283(3) Uani 1 1 d . . . . .
H3A H 0.172252 0.792451 0.243322 0.034 Uiso 1 1 calc R U . . .
C4 C 0.18002(19) 0.60353(14) 0.23551(11) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.1717(2) 0.53515(15) 0.16026(12) 0.0309(3) Uani 1 1 d . . . . .
H5 H 0.174485 0.439672 0.188248 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1598(2) 0.60376(15) 0.04713(13) 0.0316(3) Uani 1 1 d . . . . .
H6 H 0.155635 0.556555 -0.003073 0.038 Uiso 1 1 calc R U . . .
C7 C 0.22484(18) 0.54328(13) 0.44472(11) 0.0234(3) Uani 1 1 d . U . . .
C8 C 0.29865(19) 0.38854(14) 0.64599(11) 0.0243(3) Uani 1 1 d . . . . .
C9 C 0.3068(2) 0.47842(14) 0.70229(12) 0.0286(3) Uani 1 1 d . . . . .
H9 H 0.297543 0.572814 0.661671 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3283(2) 0.42961(15) 0.81756(12) 0.0295(3) Uani 1 1 d . . . . .
H10 H 0.333670 0.490385 0.856291 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3420(2) 0.29173(14) 0.87618(12) 0.0272(3) Uani 1 1 d . . . . .
C12 C 0.3374(2) 0.20059(15) 0.82182(13) 0.0317(3) Uani 1 1 d . . . . .
H12 H 0.349410 0.106194 0.862795 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3153(2) 0.24930(14) 0.70771(13) 0.0304(3) Uani 1 1 d . . . . .
H13 H 0.311248 0.187679 0.669679 0.036 Uiso 1 1 calc R U . . .
O5 O 0.30400(16) 0.23034(10) 0.40658(9) 0.0359(3) Uani 1 1 d . . . . .
C14 C 0.4794(2) 0.19694(16) 0.35350(14) 0.0376(4) Uani 1 1 d . . . . .
H14A H 0.596766 0.185951 0.401534 0.045 Uiso 1 1 calc R U . . .
H14B H 0.492833 0.269414 0.280862 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1638(2) 0.14066(17) 0.40311(15) 0.0400(4) Uani 1 1 d . . . . .
H15A H 0.033083 0.192119 0.378087 0.048 Uiso 1 1 calc R U . . .
H15B H 0.154391 0.071180 0.477843 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4567(2) 0.06650(16) 0.33705(13) 0.0366(4) Uani 1 1 d . . . . .
H16A H 0.507221 -0.012582 0.403233 0.044 Uiso 1 1 calc R U . . .
H16B H 0.524490 0.060839 0.270450 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2384(3) 0.07565(17) 0.32124(15) 0.0409(4) Uani 1 1 d . . . . .
H17A H 0.195985 -0.014976 0.339466 0.049 Uiso 1 1 calc R U . . .
H17B H 0.193708 0.132469 0.243865 0.049 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 C7 1.6611(13) . ?
O1 N1 1.2328(17) . ?
O2 N1 1.2287(17) . ?
O3 N4 1.2264(17) . ?
O4 N4 1.2263(17) . ?
N1 C1 1.4613(18) . ?
N2 H2 0.8800 . ?
N2 C4 1.3989(18) . ?
N2 C7 1.3720(17) . ?
N3 H3 0.8800 . ?
N3 C7 1.3717(18) . ?
N3 C8 1.3990(18) . ?
N4 C11 1.4590(19) . ?
C1 C2 1.384(2) . ?
C1 C6 1.389(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3987(19) . ?
C4 C5 1.4059(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.3956(19) . ?
C8 C13 1.4046(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.372(2) . ?
C13 H13 0.9500 . ?
O5 C14 1.4570(19) . ?
O5 C15 1.4494(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C16 1.505(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C17 1.509(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.509(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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 N1 C1 118.19(12) . . ?
O2 N1 O1 123.27(13) . . ?
O2 N1 C1 118.54(12) . . ?
C4 N2 H2 113.6 . . ?
C7 N2 H2 113.6 . . ?
C7 N2 C4 132.90(12) . . ?
C7 N3 H3 113.6 . . ?
C7 N3 C8 132.77(12) . . ?
C8 N3 H3 113.6 . . ?
O3 N4 O4 122.73(13) . . ?
O3 N4 C11 118.69(12) . . ?
O4 N4 C11 118.58(12) . . ?
C2 C1 N1 119.97(13) . . ?
C2 C1 C6 121.40(13) . . ?
C6 C1 N1 118.62(13) . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.75(13) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C2 C3 C4 119.85(13) . . ?
C4 C3 H3A 120.1 . . ?
N2 C4 C5 114.38(12) . . ?
C3 C4 N2 126.64(12) . . ?
C3 C4 C5 118.96(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.23(13) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.79(13) . . ?
C5 C6 H6 120.6 . . ?
N2 C7 S1 125.17(10) . . ?
N3 C7 S1 125.59(10) . . ?
N3 C7 N2 109.23(11) . . ?
N3 C8 C13 114.86(12) . . ?
C9 C8 N3 126.06(13) . . ?
C9 C8 C13 119.07(13) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.81(13) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.73(13) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 N4 119.70(13) . . ?
C12 C11 N4 118.91(13) . . ?
C12 C11 C10 121.39(14) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.72(13) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.27(13) . . ?
C12 C13 H13 119.4 . . ?
C15 O5 C14 108.15(11) . . ?
O5 C14 H14A 110.4 . . ?
O5 C14 H14B 110.4 . . ?
O5 C14 C16 106.43(13) . . ?
H14A C14 H14B 108.6 . . ?
C16 C14 H14A 110.4 . . ?
C16 C14 H14B 110.4 . . ?
O5 C15 H15A 110.5 . . ?
O5 C15 H15B 110.5 . . ?
O5 C15 C17 106.01(13) . . ?
H15A C15 H15B 108.7 . . ?
C17 C15 H15A 110.5 . . ?
C17 C15 H15B 110.5 . . ?
C14 C16 H16A 111.3 . . ?
C14 C16 H16B 111.3 . . ?
C14 C16 C17 102.25(13) . . ?
H16A C16 H16B 109.2 . . ?
C17 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
C15 C17 H17A 111.3 . . ?
C15 C17 H17B 111.3 . . ?
C16 C17 C15 102.25(13) . . ?
C16 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?

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 N1 C1 C2 173.60(14) . . . . ?
O1 N1 C1 C6 -5.2(2) . . . . ?
O2 N1 C1 C2 -5.9(2) . . . . ?
O2 N1 C1 C6 175.37(14) . . . . ?
O3 N4 C11 C10 0.0(2) . . . . ?
O3 N4 C11 C12 179.95(14) . . . . ?
O4 N4 C11 C10 -179.70(14) . . . . ?
O4 N4 C11 C12 0.2(2) . . . . ?
N1 C1 C2 C3 -178.07(13) . . . . ?
N1 C1 C6 C5 178.17(13) . . . . ?
N2 C4 C5 C6 -176.71(13) . . . . ?
N3 C8 C9 C10 -179.64(13) . . . . ?
N3 C8 C13 C12 179.53(13) . . . . ?
N4 C11 C12 C13 178.89(13) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 N2 176.62(13) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C3 C4 C5 C6 1.8(2) . . . . ?
C4 N2 C7 S1 12.8(2) . . . . ?
C4 N2 C7 N3 -168.45(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C7 N2 C4 C3 -1.6(2) . . . . ?
C7 N2 C4 C5 176.79(14) . . . . ?
C7 N3 C8 C9 -14.6(2) . . . . ?
C7 N3 C8 C13 166.62(14) . . . . ?
C8 N3 C7 S1 6.9(2) . . . . ?
C8 N3 C7 N2 -171.82(13) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C9 C10 C11 N4 -179.13(13) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C12 C13 C8 0.4(2) . . . . ?
C13 C8 C9 C10 -0.9(2) . . . . ?
O5 C14 C16 C17 30.66(16) . . . . ?
O5 C15 C17 C16 32.71(17) . . . . ?
C14 O5 C15 C17 -13.97(17) . . . . ?
C14 C16 C17 C15 -38.11(16) . . . . ?
C15 O5 C14 C16 -10.62(17) . . . . ?

_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
;
####################################################################### 
# 
# 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_chns_auto
_database_code_depnum_ccdc_archive 'CCDC 2407301'
loop_
_audit_author_name
_audit_author_address
Tao
;Nanjing University
China
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-04 downloaded from the CCDC.
;
_audit_creation_date             2024-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 N2 S'
_chemical_formula_sum            'C17 H20 N2 S'
_chemical_formula_weight         284.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNS
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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7780(2)
_cell_length_b                   9.33460(10)
_cell_length_c                   30.4546(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3063.99(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10677
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      76.8550
_cell_measurement_theta_min      2.8670
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.95a (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    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.285
_diffrn_reflns_theta_min         2.902
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  69.00   0.50    0.06    --  107.18 -57.00 150.00   68
  2  ω     35.00  69.00   0.50    0.06    --  107.18 -57.00 120.00   68
  3  ω     35.00  69.00   0.50    0.06    --  107.18 -57.00 -60.00   68
  4  ω     35.00  69.00   0.50    0.06    --  107.18 -57.00 -90.00   68
  5  ω     35.00  67.00   0.50    0.06    --  107.18 -56.00-134.00   64
  6  ω    -27.00  29.00   0.50    0.05    --   47.13 -19.00-150.00  112
  7  ω     90.00 178.00   0.50    0.06    --  107.18  95.00-123.00  176
  8  ω     94.00 178.00   0.50    0.06    --  107.18  38.00  30.00  168
  9  ω    -27.00  29.00   0.50    0.05    --   47.13 -19.00 120.00  112
 10  ω    -23.00  28.00   0.50    0.05    --  -47.13  19.00 150.00  102
 11  ω    -23.00  28.00   0.50    0.05    --  -47.13  19.00  30.00  102
 12  ω    -63.00 -30.00   0.50    0.06    -- -103.00  57.00  90.00   66
 13  ω   -119.00 -60.00   0.50    0.05    --  -47.13 -57.00 120.00  118
 14  ω   -174.00 -81.00   0.50    0.06    -- -103.00 -75.00  12.00  186
 15  ω   -119.00 -32.00   0.50    0.05    --  -47.13 -56.00-134.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0434060000
_diffrn_orient_matrix_UB_12      -0.0332862000
_diffrn_orient_matrix_UB_13      -0.0470989000
_diffrn_orient_matrix_UB_21      -0.0855216000
_diffrn_orient_matrix_UB_22      -0.1322807000
_diffrn_orient_matrix_UB_23      -0.0010733000
_diffrn_orient_matrix_UB_31      -0.1059437000
_diffrn_orient_matrix_UB_32      0.0930559000
_diffrn_orient_matrix_UB_33      -0.0183803000
_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'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             3129
_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 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.072
_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)+(0.0528P)²+1.1693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C006(H00a,H00b), C00C(H00d,H00e)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), N003(H003), C008(H008), C009(H009), C00B(H00c), C00D(H00f),
 C00E(H00g), C00G(H00h), C00H(H00i), C00I(H00j)
2.c Idealised Me refined as rotating group:
 C00J(H00k,H00l,H00m), C00K(H00n,H00o,H00p)
;
_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
S001 S 0.58461(3) -0.08619(3) 0.43353(2) 0.01986(12) Uani 1 1 d . . . . .
N002 N 0.67781(10) 0.16633(11) 0.40654(3) 0.0184(2) Uani 1 1 d . . . . .
H002 H 0.694634 0.256923 0.411883 0.022 Uiso 1 1 calc R U . . .
N003 N 0.59625(10) 0.16035(11) 0.47594(3) 0.0180(2) Uani 1 1 d . . . . .
H003 H 0.576282 0.107822 0.498874 0.022 Uiso 1 1 calc R U . . .
C004 C 0.50038(12) 0.39089(13) 0.45453(4) 0.0169(3) Uani 1 1 d . . . . .
C005 C 0.62207(12) 0.09144(13) 0.43850(4) 0.0167(3) Uani 1 1 d . . . . .
C006 C 0.59851(12) 0.31620(13) 0.48188(4) 0.0176(3) Uani 1 1 d . . . . .
H00A H 0.681350 0.353089 0.473556 0.021 Uiso 1 1 calc R U . . .
H00B H 0.584839 0.338855 0.513267 0.021 Uiso 1 1 calc R U . . .
C007 C 0.66348(12) 0.19702(14) 0.32569(4) 0.0186(3) Uani 1 1 d . . . . .
C008 C 0.53115(12) 0.50660(13) 0.42799(4) 0.0187(3) Uani 1 1 d . . . . .
H008 H 0.613971 0.541425 0.427890 0.022 Uiso 1 1 calc R U . . .
C009 C 0.55776(13) 0.28191(14) 0.32893(4) 0.0205(3) Uani 1 1 d . . . . .
H009 H 0.517881 0.293491 0.356516 0.025 Uiso 1 1 calc R U . . .
C00A C 0.32031(13) 0.52454(15) 0.40132(4) 0.0216(3) Uani 1 1 d . . . . .
C00B C 0.37743(13) 0.34556(14) 0.45548(4) 0.0226(3) Uani 1 1 d . . . . .
H00C H 0.353981 0.268563 0.474110 0.027 Uiso 1 1 calc R U . . .
C00C C 0.71283(13) 0.10994(15) 0.36366(4) 0.0225(3) Uani 1 1 d . . . . .
H00D H 0.681661 0.010545 0.361029 0.027 Uiso 1 1 calc R U . . .
H00E H 0.804478 0.106572 0.361727 0.027 Uiso 1 1 calc R U . . .
C00D C 0.51020(13) 0.34992(15) 0.29190(5) 0.0246(3) Uani 1 1 d . . . . .
H00F H 0.438188 0.407926 0.294633 0.030 Uiso 1 1 calc R U . . .
C00E C 0.44250(13) 0.57232(14) 0.40154(4) 0.0208(3) Uani 1 1 d . . . . .
H00G H 0.465753 0.650724 0.383437 0.025 Uiso 1 1 calc R U . . .
C00F C 0.56598(14) 0.33469(15) 0.25095(5) 0.0266(3) Uani 1 1 d . . . . .
C00G C 0.67302(14) 0.25198(17) 0.24825(4) 0.0288(3) Uani 1 1 d . . . . .
H00H H 0.713592 0.241446 0.220749 0.035 Uiso 1 1 calc R U . . .
C00H C 0.72162(13) 0.18451(15) 0.28509(4) 0.0252(3) Uani 1 1 d . . . . .
H00I H 0.795296 0.129277 0.282529 0.030 Uiso 1 1 calc R U . . .
C00I C 0.28848(13) 0.41215(15) 0.42934(5) 0.0242(3) Uani 1 1 d . . . . .
H00J H 0.204778 0.380536 0.430615 0.029 Uiso 1 1 calc R U . . .
C00J C 0.22537(14) 0.58813(17) 0.37061(5) 0.0305(3) Uani 1 1 d . . . . .
H00K H 0.240537 0.691137 0.367483 0.046 Uiso 1 1 calc R U . . .
H00L H 0.142035 0.572678 0.382574 0.046 Uiso 1 1 calc R U . . .
H00M H 0.231862 0.541883 0.341811 0.046 Uiso 1 1 calc R U . . .
C00K C 0.51222(17) 0.40765(19) 0.21095(5) 0.0386(4) Uani 1 1 d . . . . .
H00N H 0.421950 0.395080 0.210680 0.058 Uiso 1 1 calc R U . . .
H00O H 0.547817 0.365111 0.184361 0.058 Uiso 1 1 calc R U . . .
H00P H 0.532029 0.510071 0.211855 0.058 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
S001 C005 1.7132(13) . ?
N002 H002 0.8800 . ?
N002 C005 1.3404(16) . ?
N002 C00C 1.4578(15) . ?
N003 H003 0.8800 . ?
N003 C005 1.3387(16) . ?
N003 C006 1.4662(16) . ?
C004 C006 1.5161(18) . ?
C004 C008 1.3891(18) . ?
C004 C00B 1.3913(19) . ?
C006 H00A 0.9900 . ?
C006 H00B 0.9900 . ?
C007 C009 1.3913(19) . ?
C007 C00C 1.5101(17) . ?
C007 C00H 1.3912(18) . ?
C008 H008 0.9500 . ?
C008 C00E 1.3921(19) . ?
C009 H009 0.9500 . ?
C009 C00D 1.3920(19) . ?
C00A C00E 1.390(2) . ?
C00A C00I 1.3952(19) . ?
C00A C00J 1.5081(19) . ?
C00B H00C 0.9500 . ?
C00B C00I 1.392(2) . ?
C00C H00D 0.9900 . ?
C00C H00E 0.9900 . ?
C00D H00F 0.9500 . ?
C00D C00F 1.392(2) . ?
C00E H00G 0.9500 . ?
C00F C00G 1.391(2) . ?
C00F C00K 1.511(2) . ?
C00G H00H 0.9500 . ?
C00G C00H 1.3891(19) . ?
C00H H00I 0.9500 . ?
C00I H00J 0.9500 . ?
C00J H00K 0.9800 . ?
C00J H00L 0.9800 . ?
C00J H00M 0.9800 . ?
C00K H00N 0.9800 . ?
C00K H00O 0.9800 . ?
C00K H00P 0.9800 . ?

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
C005 N002 H002 117.3 . . ?
C005 N002 C00C 125.32(11) . . ?
C00C N002 H002 117.3 . . ?
C005 N003 H003 117.3 . . ?
C005 N003 C006 125.34(11) . . ?
C006 N003 H003 117.3 . . ?
C008 C004 C006 120.71(12) . . ?
C008 C004 C00B 118.42(12) . . ?
C00B C004 C006 120.87(11) . . ?
N002 C005 S001 123.12(10) . . ?
N003 C005 S001 119.42(10) . . ?
N003 C005 N002 117.46(11) . . ?
N003 C006 C004 112.14(10) . . ?
N003 C006 H00A 109.2 . . ?
N003 C006 H00B 109.2 . . ?
C004 C006 H00A 109.2 . . ?
C004 C006 H00B 109.2 . . ?
H00A C006 H00B 107.9 . . ?
C009 C007 C00C 122.74(11) . . ?
C00H C007 C009 118.66(12) . . ?
C00H C007 C00C 118.47(12) . . ?
C004 C008 H008 119.5 . . ?
C004 C008 C00E 121.02(12) . . ?
C00E C008 H008 119.5 . . ?
C007 C009 H009 119.9 . . ?
C007 C009 C00D 120.27(12) . . ?
C00D C009 H009 119.9 . . ?
C00E C00A C00I 118.11(12) . . ?
C00E C00A C00J 121.29(13) . . ?
C00I C00A C00J 120.57(13) . . ?
C004 C00B H00C 119.7 . . ?
C004 C00B C00I 120.54(12) . . ?
C00I C00B H00C 119.7 . . ?
N002 C00C C007 113.60(11) . . ?
N002 C00C H00D 108.8 . . ?
N002 C00C H00E 108.8 . . ?
C007 C00C H00D 108.8 . . ?
C007 C00C H00E 108.8 . . ?
H00D C00C H00E 107.7 . . ?
C009 C00D H00F 119.3 . . ?
C00F C00D C009 121.35(13) . . ?
C00F C00D H00F 119.3 . . ?
C008 C00E H00G 119.6 . . ?
C00A C00E C008 120.76(12) . . ?
C00A C00E H00G 119.6 . . ?
C00D C00F C00K 120.71(14) . . ?
C00G C00F C00D 117.91(13) . . ?
C00G C00F C00K 121.37(14) . . ?
C00F C00G H00H 119.4 . . ?
C00H C00G C00F 121.12(13) . . ?
C00H C00G H00H 119.4 . . ?
C007 C00H H00I 119.7 . . ?
C00G C00H C007 120.66(13) . . ?
C00G C00H H00I 119.7 . . ?
C00A C00I H00J 119.5 . . ?
C00B C00I C00A 121.06(13) . . ?
C00B C00I H00J 119.5 . . ?
C00A C00J H00K 109.5 . . ?
C00A C00J H00L 109.5 . . ?
C00A C00J H00M 109.5 . . ?
H00K C00J H00L 109.5 . . ?
H00K C00J H00M 109.5 . . ?
H00L C00J H00M 109.5 . . ?
C00F C00K H00N 109.5 . . ?
C00F C00K H00O 109.5 . . ?
C00F C00K H00P 109.5 . . ?
H00N C00K H00O 109.5 . . ?
H00N C00K H00P 109.5 . . ?
H00O C00K H00P 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
C004 C008 C00E C00A 0.61(19) . . . . ?
C004 C00B C00I C00A 0.7(2) . . . . ?
C005 N002 C00C C007 126.74(13) . . . . ?
C005 N003 C006 C004 64.93(16) . . . . ?
C006 N003 C005 S001 -166.52(10) . . . . ?
C006 N003 C005 N002 14.07(19) . . . . ?
C006 C004 C008 C00E 177.58(11) . . . . ?
C006 C004 C00B C00I -178.21(12) . . . . ?
C007 C009 C00D C00F 0.3(2) . . . . ?
C008 C004 C006 N003 -129.94(12) . . . . ?
C008 C004 C00B C00I 1.97(19) . . . . ?
C009 C007 C00C N002 -25.18(19) . . . . ?
C009 C007 C00H C00G -1.9(2) . . . . ?
C009 C00D C00F C00G -1.6(2) . . . . ?
C009 C00D C00F C00K 179.18(14) . . . . ?
C00B C004 C006 N003 50.25(16) . . . . ?
C00B C004 C008 C00E -2.60(18) . . . . ?
C00C N002 C005 S001 0.72(19) . . . . ?
C00C N002 C005 N003 -179.90(11) . . . . ?
C00C C007 C009 C00D -174.32(12) . . . . ?
C00C C007 C00H C00G 174.06(13) . . . . ?
C00D C00F C00G C00H 1.1(2) . . . . ?
C00E C00A C00I C00B -2.6(2) . . . . ?
C00F C00G C00H C007 0.6(2) . . . . ?
C00H C007 C009 C00D 1.4(2) . . . . ?
C00H C007 C00C N002 159.07(12) . . . . ?
C00I C00A C00E C008 2.01(19) . . . . ?
C00J C00A C00E C008 -175.81(12) . . . . ?
C00J C00A C00I C00B 175.20(13) . . . . ?
C00K C00F C00G C00H -179.64(15) . . . . ?

_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 2.178
_oxdiff_exptl_absorpt_empirical_full_min 0.461
