# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_structure_I
_database_code_depnum_ccdc_archive 'CCDC 2165358'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj'
;University of Lodz
Poland
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N S, C H4 N2 S'
_chemical_formula_sum            'C6 H9 N3 S2'
_chemical_formula_weight         187.28
_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           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                   11.4353(2)
_cell_length_b                   8.35680(10)
_cell_length_c                   18.7182(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1788.76(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7894
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.4010
_cell_measurement_theta_min      6.0890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.922
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0265
2 0 1 0.0362
-2 0 -1 0.0184
0 -1 0 0.1466
0 1 0 0.1156
-1 0 2 0.0261
1 0 -2 0.0219

_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13805
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.489
_diffrn_reflns_theta_min         4.725
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  33.00   0.50    1.50    --   47.45 -34.00   5.00  118
  2  ω    -27.00  12.00   0.50    1.50    --   47.45 -19.00-120.00   78
  3  ω     33.00 120.00   0.50    1.50    --   47.45  57.00-150.00  174
  4  ω     92.00 176.00   0.50    4.50    --  105.86  15.00-150.00  168
  5  ω     33.00  75.00   0.50    4.50    --  105.86 -61.00 120.00   84
  6  ω     50.00 132.00   0.50    4.50    --  105.86-156.00 141.00  164
  7  ω     33.00  75.00   0.50    4.50    --  105.86 -61.00 -30.00   84
  8  ω     33.00  75.00   0.50    4.50    --  105.86 -61.00 -90.00   84
  9  ω     33.00  75.00   0.50    4.50    --  105.86 -61.00-120.00   84
 10  ω     25.00 120.00   0.50    1.50    --   47.45  77.00  30.00  190
 11  ω     35.00 122.00   0.50    1.50    --   47.45  34.00 163.00  174
 12  ω    -12.00  28.00   0.50    1.50    --  -47.45  19.00  60.00   80
 13  ω     25.00 120.00   0.50    1.50    --   47.45  77.00 -90.00  190
 14  ω    -75.00 -13.00   0.50    4.50    --  -86.25  61.00 -60.00  124
 15  ω    -79.00 -13.00   0.50    4.50    --  -86.25  89.00 -55.00  132
 16  ω   -159.00 -67.00   0.50    4.50    --  -86.25 -77.00 -30.00  184
 17  ω   -120.00 -73.00   0.50    1.50    --  -47.45-125.00   0.00   94
 18  ω   -120.00 -73.00   0.50    1.50    --  -47.45-125.00  90.00   94
 19  ω   -161.00 -73.00   0.50    4.50    --  -86.25 -34.00   5.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω 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                1466
_reflns_number_total             1630
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.373
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.076
_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)+(0.0919P)²+0.1246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
S12 S 0.53907(5) 0.29119(5) 0.75784(3) 0.0483(2) Uani 1 1 d . . . . .
S4 S 0.84168(4) 0.69795(6) 0.43164(3) 0.0538(2) Uani 1 1 d . . . . .
N13 N 0.38858(18) 0.1581(2) 0.66784(10) 0.0546(4) Uani 1 1 d . . . . .
N11 N 0.36935(18) 0.4249(2) 0.68327(11) 0.0548(5) Uani 1 1 d . . . . .
C12 C 0.42454(16) 0.29063(17) 0.69883(9) 0.0396(4) Uani 1 1 d . . . . .
N1 N 0.68000(19) 0.4972(3) 0.63008(11) 0.0671(5) Uani 1 1 d . . . . .
C4 C 0.77950(15) 0.62473(19) 0.50771(9) 0.0422(4) Uani 1 1 d . . . . .
C5 C 0.65889(16) 0.6330(3) 0.52174(12) 0.0570(5) Uani 1 1 d . . . . .
H5 H 0.610089 0.683922 0.489124 0.068 Uiso 1 1 calc R U . . .
C3 C 0.84622(18) 0.5489(3) 0.56090(12) 0.0605(6) Uani 1 1 d . . . . .
H3 H 0.926829 0.541111 0.555311 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6123(2) 0.5688(3) 0.58153(13) 0.0688(6) Uani 1 1 d . . . . .
H6 H 0.531970 0.574526 0.588976 0.083 Uiso 1 1 calc R U . . .
C2 C 0.7955(2) 0.4869(3) 0.62015(13) 0.0713(7) Uani 1 1 d . . . . .
H2 H 0.841635 0.436498 0.654335 0.086 Uiso 1 1 calc R U . . .
H11A H 0.395(2) 0.517(3) 0.7011(15) 0.072(7) Uiso 1 1 d . . . . .
H11B H 0.321(2) 0.424(3) 0.6584(15) 0.060(7) Uiso 1 1 d . . . . .
H13A H 0.424(2) 0.071(3) 0.6754(13) 0.063(7) Uiso 1 1 d . . . . .
H13B H 0.337(3) 0.159(3) 0.6399(14) 0.064(7) Uiso 1 1 d . . . . .
H1 H 0.655(2) 0.457(4) 0.6688(16) 0.079(8) Uiso 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
S12 C12 1.7133(19) . ?
S4 C4 1.7050(18) . ?
N13 C12 1.316(2) . ?
N13 H13A 0.84(3) . ?
N13 H13B 0.79(3) . ?
N11 C12 1.320(2) . ?
N11 H11A 0.89(3) . ?
N11 H11B 0.73(3) . ?
N1 C6 1.336(3) . ?
N1 C2 1.337(3) . ?
N1 H1 0.85(3) . ?
C4 C5 1.406(3) . ?
C4 C3 1.405(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.354(3) . ?
C6 H6 0.9300 . ?
C2 H2 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
C12 N13 H13A 119.8(17) . . ?
C12 N13 H13B 121(2) . . ?
H13A N13 H13B 119(3) . . ?
C12 N11 H11A 119.8(17) . . ?
C12 N11 H11B 120(2) . . ?
H11A N11 H11B 120(3) . . ?
N13 C12 S12 121.70(14) . . ?
N13 C12 N11 117.95(19) . . ?
N11 C12 S12 120.36(14) . . ?
C6 N1 C2 120.5(2) . . ?
C6 N1 H1 124.0(19) . . ?
C2 N1 H1 115.5(19) . . ?
C5 C4 S4 123.19(14) . . ?
C3 C4 S4 121.81(14) . . ?
C3 C4 C5 114.99(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.49(19) . . ?
C6 C5 H5 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
N1 C6 C5 120.9(2) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C2 C3 120.8(2) . . ?
N1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 S4 0.93 2.92 3.665(3) 138.6 4_466 yes
C6 H6 S4 0.93 2.92 3.665(3) 138.6 4_466 yes
N11 H11A S12 0.89(3) 2.53(3) 3.4177(19) 175(2) 3_656 yes
N11 H11A S12 0.89(3) 2.53(3) 3.4177(19) 175(2) 3_656 yes
N11 H11B S4 0.73(3) 2.71(3) 3.392(2) 158(3) 5_666 yes
N11 H11B S4 0.73(3) 2.71(3) 3.392(2) 158(3) 5_666 yes
N13 H13A S12 0.84(3) 2.69(3) 3.468(2) 154(2) 3_646 yes
N13 H13A S12 0.84(3) 2.69(3) 3.468(2) 154(2) 3_646 yes
N13 H13B S4 0.79(3) 2.72(3) 3.442(2) 153(3) 5_666 yes
N13 H13B S4 0.79(3) 2.72(3) 3.442(2) 153(3) 5_666 yes
N1 H1 S12 0.85(3) 2.54(3) 3.359(2) 162(3) . yes
N1 H1 S12 0.85(3) 2.54(3) 3.359(2) 162(3) . yes

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
S4 C4 C5 C6 177.70(19) . . . . ?
S4 C4 C3 C2 -178.0(2) . . . . ?
C4 C5 C6 N1 1.1(4) . . . . ?
C4 C3 C2 N1 -0.5(4) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C6 N1 C2 C3 0.1(4) . . . . ?
C2 N1 C6 C5 -0.4(4) . . . . ?

_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_strucutre_II
_database_code_depnum_ccdc_archive 'CCDC 2165361'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj'
;University of Lodz
Poland
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N S, C H4 N2 S'
_chemical_formula_sum            'C6 H9 N3 S2'
_chemical_formula_weight         187.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   10.5170(2)
_cell_length_b                   10.86720(10)
_cell_length_c                   8.42870(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.920(2)
_cell_angle_gamma                90
_cell_volume                     916.59(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.5100
_cell_measurement_theta_min      5.9890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.802
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1431
0 2 1 0.1107
1 1 -2 0.1612
1 2 -1 0.1193
0 -1 -1 0.2066
0 1 1 0.0805
0 -5 -4 0.1998
-3 -6 1 0.1265
-3 -4 4 0.1437
3 6 -1 0.1293
-7 -1 1 0.0562
7 1 0 0.0524
1 1 5 0.1196

_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -1.0000 0.0000 -0.1389 0.0149 0.0240
-0.0000 2.0000 1.0000 0.2505 0.0145 -0.2329
1.0000 1.0000 -2.0000 0.2073 0.0492 0.3311
1.0000 2.0000 -1.0000 0.3190 0.0786 0.1222
0.0000 -1.0000 -1.0000 -0.1116 -0.0294 0.2089
-0.0000 1.0000 1.0000 0.1116 0.0294 -0.2089
0.0000 -5.0000 -4.0000 -0.5854 -0.1027 0.8597
-3.0000 -6.0000 1.0000 -0.9022 -0.3244 0.0033
-3.0000 -4.0000 4.0000 -0.7063 -0.2214 -0.5994
3.0000 6.0000 -1.0000 0.9022 0.3244 -0.0033
-7.0000 -1.0000 1.0000 -0.2628 -1.0093 -0.0580
7.0000 1.0000 0.0000 0.2355 1.0536 -0.1269
1.0000 1.0000 5.0000 0.0162 0.3591 -0.9632

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.494
_diffrn_reflns_theta_min         4.418
_diffrn_ambient_temperature      298
_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 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 127.00   0.50    0.12    --  105.67  15.00  30.00   70
  2  ω    100.00 126.00   0.50    0.12    --  105.67  15.00 -30.00   52
  3  ω    144.00 169.00   0.50    0.12    --  105.67  15.00 -30.00   50
  4  ω    148.00 176.00   0.50    0.12    --  105.67  15.00  30.00   56
  5  ω    113.00 139.00   0.50    0.12    --  105.67 115.00  38.00   52
  6  ω     34.00  60.00   0.50    0.12    --  105.67 -61.00 -60.00   52
  7  ω     34.00  59.00   0.50    0.05    --   47.52-115.00 -51.00   50
  8  ω     48.00 108.00   0.50    0.12    --  105.67-115.00 -51.00  120
  9  ω     61.00 102.00   0.50    0.12    --  105.67 -95.00 -30.00   82
 10  ω     94.00 146.00   0.50    0.12    --  105.67-174.00 169.00  104
 11  ω     -3.00  25.00   0.50    0.05    --  -47.52  19.00-150.00   56
 12  ω     -6.00  21.00   0.50    0.05    --  -47.52  19.00-120.00   54
 13  ω     -6.00  23.00   0.50    0.05    --  -47.52  19.00 -90.00   58
 14  ω     -8.00  21.00   0.50    0.05    --  -47.52  19.00 -60.00   58
 15  ω    -10.00  16.00   0.50    0.05    --  -47.52  19.00 -30.00   52
 16  ω    -49.00 -21.00   0.50    0.12    --  -91.75  45.00 -90.00   56
 17  ω    -70.00 -40.00   0.50    0.12    --  -91.75  61.00-120.00   60
 18  ω    -49.00 -20.00   0.50    0.12    --  -91.75  45.00-180.00   58
 19  ω    -48.00 -23.00   0.50    0.12    --  -91.75  45.00-120.00   50
 20  ω    -71.00 -31.00   0.50    0.12    --  -91.75  61.00  30.00   80
 21  ω    -72.00 -19.00   0.50    0.12    --  -91.75  61.00  60.00  106
 22  ω    -48.00 -20.00   0.50    0.12    --  -91.75  45.00  60.00   56
 23  ω   -140.00 -85.00   0.50    0.12    --  -91.75-115.00 -51.00  110
 24  ω    -71.00 -45.00   0.50    0.05    --  -47.52-174.00 169.00   52
 25  ω    -48.00 -17.00   0.50    0.05    --  -47.52 115.00  38.00   62
 26  ω    -81.00 -54.00   0.50    0.05    --  -47.52 115.00  38.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0137904000
_diffrn_orient_matrix_UB_12      0.1389261000
_diffrn_orient_matrix_UB_13      -0.0273080000
_diffrn_orient_matrix_UB_21      0.1526332000
_diffrn_orient_matrix_UB_22      -0.0148725000
_diffrn_orient_matrix_UB_23      0.0442585000
_diffrn_orient_matrix_UB_31      -0.0147008000
_diffrn_orient_matrix_UB_32      -0.0240215000
_diffrn_orient_matrix_UB_33      -0.1848979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1528
_reflns_number_total             1685
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.336
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0051(10)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.089
_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)+(0.0673P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
S12 S -0.02732(6) 0.53881(5) 0.23781(6) 0.0535(2) Uani 1 1 d . . . . .
S2 S 0.64401(5) 0.85056(5) 0.58475(8) 0.0563(2) Uani 1 1 d . . . . .
N11 N 0.1384(2) 0.38308(18) 0.4397(2) 0.0502(5) Uani 1 1 d . . . . .
N13 N 0.1364(2) 0.37702(19) 0.1706(2) 0.0559(5) Uani 1 1 d . . . . .
N1 N 0.38533(19) 0.85845(18) 0.5531(3) 0.0561(5) Uani 1 1 d . . . . .
C12 C 0.08891(19) 0.42610(16) 0.2858(2) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.4950(2) 0.78768(17) 0.5840(3) 0.0454(5) Uani 1 1 d . . . . .
C3 C 0.4768(3) 0.6639(2) 0.6188(4) 0.0670(7) Uani 1 1 d . . . . .
H3 H 0.548454 0.609732 0.638952 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2649(3) 0.8184(3) 0.5590(4) 0.0746(8) Uani 1 1 d . . . . .
H6 H 0.193411 0.872817 0.538371 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3566(3) 0.6217(3) 0.6238(4) 0.0868(10) Uani 1 1 d . . . . .
H4 H 0.346951 0.539205 0.647075 0.104 Uiso 1 1 calc R U . . .
C5 C 0.2490(3) 0.6998(3) 0.5946(5) 0.0868(10) Uani 1 1 d . . . . .
H5 H 0.166920 0.671237 0.599464 0.104 Uiso 1 1 calc R U . . .
H11A H 0.106(2) 0.412(2) 0.515(3) 0.044(6) Uiso 1 1 d . . . . .
H11B H 0.193(3) 0.325(2) 0.457(3) 0.053(7) Uiso 1 1 d . . . . .
H1 H 0.390(3) 0.933(3) 0.534(3) 0.065(8) Uiso 1 1 d . . . . .
H13A H 0.102(3) 0.397(3) 0.072(3) 0.056(7) Uiso 1 1 d . . . . .
H13B H 0.193(3) 0.318(3) 0.197(3) 0.064(8) Uiso 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
S12 C12 1.6893(19) . ?
S2 C2 1.708(2) . ?
N11 C12 1.326(2) . ?
N11 H11A 0.87(2) . ?
N11 H11B 0.84(3) . ?
N13 C12 1.332(2) . ?
N13 H13A 0.82(3) . ?
N13 H13B 0.86(3) . ?
N1 C2 1.343(3) . ?
N1 C6 1.354(3) . ?
N1 H1 0.83(3) . ?
C2 C3 1.402(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.346(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(5) . ?
C5 H5 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
C12 N11 H11A 117.8(15) . . ?
C12 N11 H11B 118.8(17) . . ?
H11A N11 H11B 123(2) . . ?
C12 N13 H13A 118.6(18) . . ?
C12 N13 H13B 120.0(18) . . ?
H13A N13 H13B 121(3) . . ?
C2 N1 C6 124.5(2) . . ?
C2 N1 H1 120(2) . . ?
C6 N1 H1 116(2) . . ?
N11 C12 S12 121.80(14) . . ?
N11 C12 N13 116.74(18) . . ?
N13 C12 S12 121.45(15) . . ?
N1 C2 S2 120.26(15) . . ?
N1 C2 C3 115.2(2) . . ?
C3 C2 S2 124.56(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
N1 C6 H6 120.1 . . ?
C5 C6 N1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11A S12 0.87(2) 2.52(2) 3.3804(18) 170(2) 3_566 yes
N11 H11B S2 0.84(3) 2.66(3) 3.467(2) 163(2) 3_666 yes
N1 H1 S2 0.83(3) 2.54(3) 3.350(2) 166(3) 3_676 yes
N13 H13A S12 0.82(3) 2.58(3) 3.402(2) 172(2) 3_565 yes
N13 H13B S2 0.86(3) 2.78(3) 3.574(2) 154(2) 3_666 yes

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
S2 C2 C3 C4 176.8(2) . . . . ?
N1 C2 C3 C4 -1.3(4) . . . . ?
N1 C6 C5 C4 -0.3(5) . . . . ?
C2 N1 C6 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C6 N1 C2 S2 -176.2(2) . . . . ?
C6 N1 C2 C3 2.0(4) . . . . ?

_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.666
####################################################################### 
# 
# 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_structure_IV
_database_code_depnum_ccdc_archive 'CCDC 2165359'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj'
;University of Lodz
Poland
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 N3 S3, C5 H5 N S'
_chemical_formula_sum            'C8 H8 N4 S4'
_chemical_formula_weight         288.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   4.19560(10)
_cell_length_b                   10.8480(3)
_cell_length_c                   13.5301(4)
_cell_angle_alpha                99.138(2)
_cell_angle_beta                 93.308(2)
_cell_angle_gamma                93.370(2)
_cell_volume                     605.53(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3965
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.8390
_cell_measurement_theta_min      3.2930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.034
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.2434
-1 0 0 0.2689
0 2 1 0.0373
0 -2 -1 0.0074
0 -1 2 0.0490
0 1 -2 0.0010

_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.045
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -0.0000 -0.0000 0.0544 -0.0614 0.3594
-1.0000 0.0000 0.0000 -0.0544 0.0614 -0.3594
-0.0000 2.0000 1.0000 0.2837 -0.1585 -0.0416
0.0000 -2.0000 -1.0000 -0.2837 0.1585 0.0416
-0.0000 -1.0000 2.0000 0.1069 0.2262 0.0284
0.0000 1.0000 -2.0000 -0.1069 -0.2262 -0.0284

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.481
_diffrn_reflns_theta_min         3.316
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -80.00   0.50    0.05    --  -47.45-131.00 175.00   76
  2  ω   -139.00-114.00   0.50    0.15    --  -86.25-131.00 175.00   50
  3  ω   -114.00 -64.00   0.50    0.05    --  -47.45-139.00   0.00  100
  4  ω    -99.00 -26.00   0.50    0.05    --  -47.45 -77.00-120.00  146
  5  ω     -5.00  27.00   0.50    0.05    --  -47.45  19.00   0.00   64
  6  ω    -48.00 -14.00   0.50    0.15    --  -86.25  45.00   0.00   68
  7  ω    -46.00 -21.00   0.50    0.15    --  -86.25  45.00  30.00   50
  8  ω    -75.00 -50.00   0.50    0.05    --  -47.45 139.00  61.00   50
  9  ω    -89.00 -64.00   0.50    0.15    --  -86.25 139.00  61.00   50
 10  ω    -78.00 -50.00   0.50    0.05    --  -47.45 131.00-113.00   56
 11  ω    -77.00 -51.00   0.50    0.15    --  -86.25 131.00-113.00   52
 12  ω    -48.00 -15.00   0.50    0.15    --  -86.25  45.00-180.00   66
 13  ω    -49.00 -18.00   0.50    0.15    --  -86.25  45.00-150.00   62
 14  ω   -112.00 -73.00   0.50    0.15    --  -86.25 -15.00  30.00   78
 15  ω   -135.00-110.00   0.50    0.15    --  -86.25-139.00   0.00   50
 16  ω   -160.00-115.00   0.50    0.15    --  -86.25 -15.00  30.00   90
 17  ω    -25.00   1.00   0.50    0.05    --   47.45 -19.00-180.00   52
 18  ω    -14.00  11.00   0.50    0.05    --   47.45 -19.00 -90.00   50
 19  ω     49.00  75.00   0.50    0.15    --  105.86 -61.00 -30.00   52
 20  ω     78.00 105.00   0.50    0.15    --  105.86 -95.00   0.00   54
 21  ω     77.00 120.00   0.50    0.15    --  105.86-139.00   0.00   86
 22  ω     67.00  98.00   0.50    0.05    --   47.45-139.00   0.00   62
 23  ω     40.00  74.00   0.50    0.15    --  105.86 -61.00  60.00   68
 24  ω     34.00  63.00   0.50    0.15    --  105.86 -61.00  30.00   58
 25  ω     35.00  78.00   0.50    0.15    --  105.86-125.00  30.00   86
 26  ω     41.00  75.00   0.50    0.15    --  105.86 -61.00 150.00   68
 27  ω     69.00  94.00   0.50    0.15    --  105.86-131.00 175.00   50
 28  ω     67.00  93.00   0.50    0.05    --   47.45-131.00 175.00   52
 29  ω     93.00 176.00   0.50    0.15    --  105.86  45.00 -60.00  166
 30  ω    106.00 132.00   0.50    0.15    --  105.86 139.00  61.00   52
 31  ω    126.00 175.00   0.50    0.15    --  105.86 131.00-113.00   98
 32  ω    153.00 178.00   0.50    0.15    --  105.86 125.00-180.00   50
 33  ω    119.00 145.00   0.50    0.15    --  105.86 125.00-180.00   52
 34  ω     93.00 121.00   0.50    0.15    --  105.86 131.00-113.00   56
 35  ω    117.00 175.00   0.50    0.15    --  105.86  45.00-180.00  116
 36  ω     96.00 168.00   0.50    0.15    --  105.86  15.00 -90.00  144
 37  ω     72.00 102.00   0.50    0.15    --  105.86-125.00-150.00   60
 38  ω     49.00  74.00   0.50    0.15    --  105.86 -61.00-150.00   50
 39  ω     43.00  69.00   0.50    0.15    --  105.86 -61.00-120.00   52
 40  ω     42.00  75.00   0.50    0.15    --  105.86 -61.00-180.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0543887000
_diffrn_orient_matrix_UB_12      0.0921182000
_diffrn_orient_matrix_UB_13      0.0994962000
_diffrn_orient_matrix_UB_21      -0.0613745000
_diffrn_orient_matrix_UB_22      -0.1086543000
_diffrn_orient_matrix_UB_23      0.0587633000
_diffrn_orient_matrix_UB_31      0.3594391000
_diffrn_orient_matrix_UB_32      -0.0222963000
_diffrn_orient_matrix_UB_33      0.0030424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1940
_reflns_number_total             2201
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.300
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0206(13)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.061
_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)+(0.0466P)²+0.0050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_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
S16 S 0.95075(12) 0.90900(5) 0.25164(4) 0.04172(17) Uani 1 1 d . . . . .
S12 S 0.19238(13) 0.84319(5) -0.08055(4) 0.04467(18) Uani 1 1 d . . . . .
S14 S 0.25861(13) 0.48141(4) 0.13528(4) 0.04441(18) Uani 1 1 d . . . . .
S2 S 0.84356(14) 0.58823(5) 0.37484(4) 0.04635(18) Uani 1 1 d . . . . .
N13 N 0.2562(4) 0.67497(14) 0.03872(12) 0.0348(4) Uani 1 1 d . . . . .
N15 N 0.5872(4) 0.70063(14) 0.18324(12) 0.0340(4) Uani 1 1 d . . . . .
N11 N 0.5647(4) 0.85758(15) 0.08704(12) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.7576(5) 0.64575(17) 0.56843(13) 0.0442(4) Uani 1 1 d . . . . .
C2 C 0.7082(5) 0.67781(18) 0.47653(15) 0.0363(4) Uani 1 1 d . . . . .
C16 C 0.6915(4) 0.81968(17) 0.17236(14) 0.0317(4) Uani 1 1 d . . . . .
C12 C 0.3451(4) 0.79108(17) 0.01880(14) 0.0320(4) Uani 1 1 d . . . . .
C14 C 0.3719(4) 0.62449(16) 0.11881(14) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.5430(5) 0.7870(2) 0.47437(17) 0.0470(5) Uani 1 1 d . . . . .
H3 H 0.498500 0.813858 0.413415 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5113(6) 0.8161(2) 0.65271(18) 0.0538(6) Uani 1 1 d . . . . .
H5 H 0.449460 0.862438 0.711495 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4480(6) 0.8533(2) 0.55999(19) 0.0531(6) Uani 1 1 d . . . . .
H4 H 0.338845 0.924924 0.556756 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6652(7) 0.7106(2) 0.65441(18) 0.0558(6) Uani 1 1 d . . . . .
H6 H 0.707819 0.682479 0.714959 0.067 Uiso 1 1 calc R U . . .
H15 H 0.660(5) 0.676(2) 0.237(2) 0.044(6) Uiso 1 1 d . . . . .
H1 H 0.860(6) 0.580(3) 0.571(2) 0.053(7) Uiso 1 1 d . . . . .
H13 H 0.124(6) 0.633(2) -0.0047(19) 0.044(6) Uiso 1 1 d . . . . .
H11 H 0.621(6) 0.929(3) 0.0834(19) 0.045(6) Uiso 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
S16 C16 1.6382(19) . ?
S12 C12 1.6498(19) . ?
S14 C14 1.6493(18) . ?
S2 C2 1.700(2) . ?
N13 C12 1.365(2) . ?
N13 C14 1.367(2) . ?
N13 H13 0.84(3) . ?
N15 C16 1.372(2) . ?
N15 C14 1.361(2) . ?
N15 H15 0.86(3) . ?
N11 C16 1.375(2) . ?
N11 C12 1.354(3) . ?
N11 H11 0.81(3) . ?
N1 C2 1.351(3) . ?
N1 C6 1.350(3) . ?
N1 H1 0.86(3) . ?
C2 C3 1.410(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.394(4) . ?
C5 C6 1.349(4) . ?
C4 H4 0.9300 . ?
C6 H6 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
C12 N13 C14 125.39(17) . . ?
C12 N13 H13 113.9(17) . . ?
C14 N13 H13 120.7(17) . . ?
C16 N15 H15 115.2(17) . . ?
C14 N15 C16 124.97(16) . . ?
C14 N15 H15 119.7(17) . . ?
C16 N11 H11 112.7(18) . . ?
C12 N11 C16 126.12(17) . . ?
C12 N11 H11 120.9(18) . . ?
C2 N1 H1 116.1(18) . . ?
C6 N1 C2 124.92(19) . . ?
C6 N1 H1 118.9(18) . . ?
N1 C2 S2 119.75(15) . . ?
N1 C2 C3 115.02(19) . . ?
C3 C2 S2 125.23(15) . . ?
N15 C16 S16 123.68(14) . . ?
N15 C16 N11 114.06(17) . . ?
N11 C16 S16 122.24(14) . . ?
N13 C12 S12 121.67(15) . . ?
N11 C12 S12 124.04(14) . . ?
N11 C12 N13 114.29(16) . . ?
N13 C14 S14 122.15(15) . . ?
N15 C14 S14 122.74(14) . . ?
N15 C14 N13 115.11(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.91(19) . . ?
C4 C3 H3 119.5 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.8(2) . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C6 H6 119.9 . . ?
C5 C6 N1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 S14 0.93 2.90 3.794(2) 160.8 2_666 yes
N15 H15 S2 0.86(3) 2.34(3) 3.1937(17) 174(2) . yes
N1 H1 S2 0.86(3) 2.45(3) 3.2867(19) 165(2) 2_766 yes
N13 H13 S14 0.84(3) 2.45(3) 3.2862(18) 178(2) 2_565 yes
N11 H11 S12 0.81(3) 2.56(3) 3.3608(17) 177(2) 2_675 yes

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
S2 C2 C3 C4 -179.08(19) . . . . ?
N1 C2 C3 C4 0.8(3) . . . . ?
C2 N1 C6 C5 0.0(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C16 N15 C14 S14 179.31(15) . . . . ?
C16 N15 C14 N13 -0.4(3) . . . . ?
C16 N11 C12 S12 177.93(15) . . . . ?
C16 N11 C12 N13 -1.9(3) . . . . ?
C12 N13 C14 S14 -178.14(15) . . . . ?
C12 N13 C14 N15 1.6(3) . . . . ?
C12 N11 C16 S16 -178.54(14) . . . . ?
C12 N11 C16 N15 2.9(3) . . . . ?
C14 N13 C12 S12 179.64(15) . . . . ?
C14 N13 C12 N11 -0.5(3) . . . . ?
C14 N15 C16 S16 179.85(14) . . . . ?
C14 N15 C16 N11 -1.6(3) . . . . ?
C4 C5 C6 N1 1.1(4) . . . . ?
C6 N1 C2 S2 178.99(18) . . . . ?
C6 N1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -1.1(4) . . . . ?

_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.801
####################################################################### 
# 
# 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_structure_III
_database_code_depnum_ccdc_archive 'CCDC 2165360'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj'
;University of Lodz
Poland
;
_audit_update_record             
;
2022-06-15 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_audit_creation_date             2022-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 N3 S3, C5 H5 N S'
_chemical_formula_sum            'C8 H8 N4 S4'
_chemical_formula_weight         288.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.11400(10)
_cell_length_b                   12.37150(10)
_cell_length_c                   23.8214(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.3200(10)
_cell_angle_gamma                90
_cell_volume                     1212.40(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24921
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.2770
_cell_measurement_theta_min      3.7170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.026
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0130
-2 0 -1 0.0339
0 -1 -2 0.0166
0 1 2 0.0107
0 -1 15 0.0094
0 -6 11 0.0159
0 8 -1 0.0071
3 2 0 0.0139

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 1.0012 -1.9985 -0.1537 -0.0679 -0.0632
-1.9998 0.0008 -1.0053 0.0662 0.3402 -0.6675
0.0003 -0.9987 -2.0019 -0.0929 0.1448 0.0513
-0.0003 0.9987 2.0019 0.0929 -0.1448 -0.0513
0.0645 -0.7207 15.3964 0.9669 -0.2311 0.1084
0.3684 -5.6647 10.7432 0.8114 0.3356 0.4785
0.1747 8.0020 -0.8182 -0.3058 -0.8629 -0.4023
2.5743 2.1303 0.1066 -0.2234 -0.6416 0.7338

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            52585
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.500
_diffrn_reflns_theta_min         3.711
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  28.00   0.50    1.28    --  -47.64  19.00-180.00   80
  2  ω    -39.00  25.00   0.50    1.28    --  -47.64  38.00 -60.00  128
  3  ω    -62.00  25.00   0.50    1.28    --  -47.64  57.00 150.00  174
  4  ω   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00   0.00  170
  5  ω     34.00  95.00   0.50    1.28    --   47.64-125.00  30.00  122
  6  ω    -75.00 -19.00   0.50    5.13    --  -91.75  61.00 -30.00  112
  7  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00-120.00  168
  8  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00 -30.00   58
  9  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00   0.00   58
 10  ω   -114.00 -19.00   0.50    5.13    --  -91.75  77.00 -30.00  190
 11  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00-180.00   58
 12  ω   -114.00 -19.00   0.50    5.13    --  -91.75  77.00 150.00  190
 13  ω   -166.00 -79.00   0.50    5.13    --  -91.75 -30.00   0.00  174
 14  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00-120.00   58
 15  ω     33.00 105.00   0.50    5.13    --  105.80 -95.00 120.00  144
 16  ω     92.00 176.00   0.50    5.13    --  105.80  15.00 120.00  168
 17  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00-180.00   84
 18  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00 -30.00   84
 19  ω     33.00 105.00   0.50    5.13    --  105.80 -95.00 -30.00  144
 20  ω     34.00 112.00   0.50    5.13    --  105.80-125.00 120.00  156
 21  ω     34.00 112.00   0.50    5.13    --  105.80-125.00-180.00  156
 22  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00 150.00   84
 23  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00   0.00   84
 24  ω     92.00 176.00   0.50    5.13    --  105.80  15.00  90.00  168
 25  ω     92.00 176.00   0.50    5.13    --  105.80  15.00-180.00  168
 26  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00-150.00   84
 27  ω     33.00 105.00   0.50    5.13    --  105.80 -95.00  30.00  144
 28  ω   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00 -60.00  170
 29  ω   -120.00 -25.00   0.50    1.28    --  -47.64 -77.00 -60.00  190
 30  ω     25.00 120.00   0.50    1.28    --   47.64  77.00  60.00  190
 31  ω     25.00 120.00   0.50    1.28    --   47.64  77.00-150.00  190
 32  ω     25.00 120.00   0.50    1.28    --   47.64  77.00 150.00  190
 33  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-150.00  176
 34  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-180.00  188
 35  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00 -60.00  168
 36  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 150.00  188
 37  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  30.00  176
 38  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 120.00  176
 39  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-120.00  176
 40  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  60.00  188
 41  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 120.00  188
 42  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00   0.00  188
 43  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00  60.00   58
 44  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 -30.00  176
 45  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -60.00  188
 46  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-150.00  188
 47  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00  90.00  168
 48  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-180.00  176
 49  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 -90.00  176
 50  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  30.00  188
 51  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-120.00  188
 52  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  90.00  188
 53  ω   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00 150.00  170
 54  ω    -12.00  28.00   0.50    1.28    --  -47.64  19.00  30.00   80
 55  ω   -120.00 -25.00   0.50    1.28    --  -47.64 -77.00 -30.00  190
 56  ω     25.00 120.00   0.50    1.28    --   47.64  77.00   0.00  190
 57  ω     25.00 120.00   0.50    1.28    --   47.64  77.00 120.00  190
 58  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -90.00  188
 59  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  90.00  176
 60  ω   -163.00 -83.00   0.50    5.13    --  -91.75 -95.00   0.00  160
 61  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00  30.00   58
 62  ω    -49.00 -20.00   0.50    5.13    --  -91.75  45.00 -60.00   58
 63  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 150.00  176
 64  ω   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -30.00  188
 65  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00 150.00  168
 66  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00   0.00  176
 67  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00   0.00  168
 68  ω   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00-150.00  168
 69  ω   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  60.00  176
 70  ω     33.00  75.00   0.50    5.13    --  105.80 -61.00  60.00   84
 71  ω     33.00  94.00   0.50    5.13    --  105.80 -77.00 -30.00  122
 72  ω     33.00 129.00   0.50    5.13    --  105.80 -77.00 -60.00  192
 73  ω     33.00 129.00   0.50    5.13    --  105.80 -77.00 -90.00  192
 74  ω     33.00 129.00   0.50    5.13    --  105.80 -77.00-120.00  192
 75  ω     33.00 129.00   0.50    5.13    --  105.80 -77.00-150.00  192
 76  ω     33.00 129.00   0.50    5.13    --  105.80 -77.00-180.00  192
 77  ω     83.00 178.00   0.50    5.13    --  105.80  77.00 -60.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0640778000
_diffrn_orient_matrix_UB_12      -0.0305131000
_diffrn_orient_matrix_UB_13      0.0616391000
_diffrn_orient_matrix_UB_21      -0.1604611000
_diffrn_orient_matrix_UB_22      -0.1063130000
_diffrn_orient_matrix_UB_23      -0.0193136000
_diffrn_orient_matrix_UB_31      0.3322753000
_diffrn_orient_matrix_UB_32      -0.0572219000
_diffrn_orient_matrix_UB_33      0.0029686000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2076
_reflns_number_total             2210
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.263
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.053
_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)+(0.0260P)²+0.5741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
S12 S 0.29981(12) 0.47960(3) 0.57314(2) 0.04440(13) Uani 1 1 d . . . . .
S4 S 0.89460(12) 0.27112(3) 0.68090(2) 0.04399(13) Uani 1 1 d . . . . .
S14 S 0.67936(14) 0.07252(4) 0.57577(2) 0.05109(15) Uani 1 1 d . . . . .
S16 S 0.01849(16) 0.22455(4) 0.40245(2) 0.06422(18) Uani 1 1 d . . . . .
N13 N 0.4762(4) 0.27453(11) 0.56649(6) 0.0373(3) Uani 1 1 d . . . . .
N11 N 0.1768(4) 0.33907(12) 0.49206(6) 0.0398(3) Uani 1 1 d . . . . .
N15 N 0.3488(4) 0.16320(13) 0.49263(6) 0.0432(4) Uani 1 1 d . . . . .
N1 N 1.1523(5) 0.57320(14) 0.77404(7) 0.0548(4) Uani 1 1 d . . . . .
C12 C 0.3181(4) 0.36020(13) 0.54302(7) 0.0346(3) Uani 1 1 d . . . . .
C14 C 0.4936(4) 0.17403(13) 0.54391(7) 0.0368(4) Uani 1 1 d . . . . .
C4 C 0.9839(4) 0.38643(13) 0.71730(7) 0.0358(4) Uani 1 1 d . . . . .
C16 C 0.1879(5) 0.24287(14) 0.46427(7) 0.0403(4) Uani 1 1 d . . . . .
C5 C 0.8882(5) 0.48912(14) 0.69832(7) 0.0432(4) Uani 1 1 d . . . . .
H5 H 0.764137 0.495102 0.665717 0.052 Uiso 1 1 calc R U . . .
C3 C 1.1607(5) 0.38473(15) 0.76818(8) 0.0482(5) Uani 1 1 d . . . . .
H3 H 1.222587 0.318863 0.783723 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9737(6) 0.57938(16) 0.72671(8) 0.0525(5) Uani 1 1 d . . . . .
H6 H 0.908234 0.646620 0.713347 0.063 Uiso 1 1 calc R U . . .
C2 C 1.2415(6) 0.47803(17) 0.79472(9) 0.0551(5) Uani 1 1 d . . . . .
H2 H 1.361328 0.475265 0.827914 0.066 Uiso 1 1 calc R U . . .
H13 H 0.568(5) 0.2831(17) 0.5963(9) 0.048(6) Uiso 1 1 d . . . . .
H11 H 0.088(5) 0.3879(18) 0.4761(9) 0.047(6) Uiso 1 1 d . . . . .
H15 H 0.359(5) 0.1015(19) 0.4774(9) 0.053(6) Uiso 1 1 d . . . . .
H1 H 1.223(6) 0.630(2) 0.7893(11) 0.074(8) Uiso 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
S12 C12 1.6440(17) . ?
S4 C4 1.7083(17) . ?
S14 C14 1.6525(17) . ?
S16 C16 1.6415(17) . ?
N13 C12 1.362(2) . ?
N13 C14 1.357(2) . ?
N13 H13 0.81(2) . ?
N11 C12 1.368(2) . ?
N11 C16 1.363(2) . ?
N11 H11 0.80(2) . ?
N15 C14 1.363(2) . ?
N15 C16 1.364(2) . ?
N15 H15 0.85(2) . ?
N1 C6 1.344(3) . ?
N1 C2 1.327(3) . ?
N1 H1 0.84(3) . ?
C4 C5 1.404(2) . ?
C4 C3 1.410(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.357(3) . ?
C6 H6 0.9300 . ?
C2 H2 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
C12 N13 H13 118.5(15) . . ?
C14 N13 C12 125.20(15) . . ?
C14 N13 H13 116.3(15) . . ?
C12 N11 H11 117.9(15) . . ?
C16 N11 C12 125.63(15) . . ?
C16 N11 H11 116.4(15) . . ?
C14 N15 C16 125.55(15) . . ?
C14 N15 H15 116.9(15) . . ?
C16 N15 H15 117.6(15) . . ?
C6 N1 H1 120.2(18) . . ?
C2 N1 C6 120.70(17) . . ?
C2 N1 H1 118.9(18) . . ?
N13 C12 S12 122.89(13) . . ?
N13 C12 N11 114.52(15) . . ?
N11 C12 S12 122.59(13) . . ?
N13 C14 S14 122.65(13) . . ?
N13 C14 N15 114.95(15) . . ?
N15 C14 S14 122.40(13) . . ?
C5 C4 S4 122.21(13) . . ?
C5 C4 C3 115.63(16) . . ?
C3 C4 S4 122.16(13) . . ?
N11 C16 S16 122.76(13) . . ?
N11 C16 N15 114.08(15) . . ?
N15 C16 S16 123.16(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.00(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.79(18) . . ?
C2 C3 H3 119.6 . . ?
N1 C6 C5 120.82(18) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C2 C3 121.01(18) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 S12 0.93 2.92 3.8321(19) 168.7 . yes
N13 H13 S4 0.81(2) 2.42(2) 3.2153(15) 168(2) . yes
N11 H11 S12 0.80(2) 2.57(2) 3.3549(16) 169(2) 3_566 yes
N15 H15 S14 0.85(2) 2.50(2) 3.3423(16) 172(2) 3_656 yes
N1 H1 S4 0.84(3) 2.45(3) 3.2558(18) 160(2) 2_756 yes

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
S4 C4 C5 C6 -177.20(16) . . . . ?
S4 C4 C3 C2 176.76(17) . . . . ?
C12 N13 C14 S14 -177.84(14) . . . . ?
C12 N13 C14 N15 2.7(3) . . . . ?
C12 N11 C16 S16 -178.61(15) . . . . ?
C12 N11 C16 N15 2.1(3) . . . . ?
C14 N13 C12 S12 178.76(14) . . . . ?
C14 N13 C12 N11 -1.6(3) . . . . ?
C14 N15 C16 S16 179.97(15) . . . . ?
C14 N15 C16 N11 -0.7(3) . . . . ?
C4 C5 C6 N1 -0.2(3) . . . . ?
C4 C3 C2 N1 1.1(3) . . . . ?
C16 N11 C12 S12 178.64(15) . . . . ?
C16 N11 C12 N13 -1.0(3) . . . . ?
C16 N15 C14 S14 179.07(15) . . . . ?
C16 N15 C14 N13 -1.5(3) . . . . ?
C5 C4 C3 C2 -2.8(3) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C6 N1 C2 C3 1.3(3) . . . . ?
C2 N1 C6 C5 -1.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.308
_oxdiff_exptl_absorpt_empirical_full_min 0.645
