# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

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

data_tor_thinb
_database_code_depnum_ccdc_archive 'CCDC 2091571'
loop_
_audit_author_name
_audit_author_address
'Jake Bailey'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 O S'
_chemical_formula_sum            'C6 H4 N2 O S'
_chemical_formula_weight         152.17
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   13.0765(12)
_cell_length_b                   3.7722(4)
_cell_length_c                   25.105(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.809(5)
_cell_angle_gamma                90
_cell_volume                     1207.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1067 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8513. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7242
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         1.629
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1804
_reflns_number_total             2454
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.049
_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)+(0.0364P)²+0.7216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0948
_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
 N1-H1 = N1'-H1'
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C1'(H1'A), 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
S1 S -0.02614(5) 0.0056(2) 0.37322(3) 0.01636(18) Uani 1 1 d . . . . .
O1 O 0.17420(15) 0.4006(5) 0.53986(7) 0.0180(5) Uani 1 1 d . . . . .
N1 N 0.30194(18) 0.1393(6) 0.50483(9) 0.0152(5) Uani 1 1 d D . . . .
H1 H 0.3511(18) 0.215(7) 0.5316(9) 0.018 Uiso 1 1 d DR . . . .
N2 N 0.27596(17) -0.1393(6) 0.41842(9) 0.0155(5) Uani 1 1 d . . . . .
C1 C 0.0220(2) 0.1662(7) 0.43752(10) 0.0140(6) Uani 1 1 d . . . . .
H1A H -0.027(2) 0.283(8) 0.4555(11) 0.017 Uiso 1 1 d R . . . .
C2 C 0.1281(2) 0.1181(7) 0.45257(10) 0.0127(6) Uani 1 1 d . . . . .
C3 C 0.1985(2) 0.2343(7) 0.50277(10) 0.0138(6) Uani 1 1 d . . . . .
C4 C 0.3346(2) -0.0389(7) 0.46422(10) 0.0154(6) Uani 1 1 d . . . . .
H4 H 0.407178 -0.093842 0.470282 0.018 Uiso 1 1 calc R . . . .
C5 C 0.1698(2) -0.0540(7) 0.41100(10) 0.0141(6) Uani 1 1 d . . . . .
C6 C 0.0943(2) -0.1259(7) 0.36474(10) 0.0150(6) Uani 1 1 d . . . . .
H6 H 0.107188 -0.233384 0.332638 0.018 Uiso 1 1 calc R . . . .
S1' S 0.30061(5) 0.9684(2) 0.69789(3) 0.01666(19) Uani 1 1 d . . . . .
O1' O 0.47505(14) 0.4468(5) 0.57472(7) 0.0192(5) Uani 1 1 d . . . . .
N1' N 0.61140(17) 0.5292(7) 0.64714(8) 0.0153(5) Uani 1 1 d D . . . .
H1' H 0.6515(19) 0.432(7) 0.6279(10) 0.018 Uiso 1 1 d DR . . . .
N2' N 0.60347(18) 0.8082(6) 0.73099(9) 0.0168(5) Uani 1 1 d . . . . .
C1' C 0.3386(2) 0.7781(7) 0.64404(10) 0.0164(6) Uani 1 1 d . . . . .
H1'A H 0.292596 0.717894 0.610363 0.020 Uiso 1 1 calc R . . . .
C2' C 0.4451(2) 0.7234(7) 0.65602(10) 0.0136(6) Uani 1 1 d . . . . .
C3' C 0.5079(2) 0.5565(7) 0.62180(10) 0.0140(6) Uani 1 1 d . . . . .
C4' C 0.6541(2) 0.6552(7) 0.69871(10) 0.0157(6) Uani 1 1 d . . . . .
H4' H 0.727613 0.627108 0.711755 0.019 Uiso 1 1 calc R . . . .
C5' C 0.4954(2) 0.8411(7) 0.70988(10) 0.0139(6) Uani 1 1 d . . . . .
C6' C 0.4247(2) 0.9800(8) 0.73707(10) 0.0158(6) Uani 1 1 d . . . . .
H6' H 0.442637 1.071139 0.773222 0.019 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.708(3) . ?
S1 C6 1.709(3) . ?
O1 C3 1.222(3) . ?
N1 H1 0.869(17) . ?
N1 C3 1.390(3) . ?
N1 C4 1.366(3) . ?
N2 C4 1.289(3) . ?
N2 C5 1.397(3) . ?
C1 H1A 0.97(3) . ?
C1 C2 1.367(4) . ?
C2 C3 1.453(4) . ?
C2 C5 1.435(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9500 . ?
S1' C1' 1.699(3) . ?
S1' C6' 1.701(3) . ?
O1' C3' 1.236(3) . ?
N1' H1' 0.869(17) . ?
N1' C3' 1.366(3) . ?
N1' C4' 1.376(3) . ?
N2' C4' 1.291(3) . ?
N2' C5' 1.400(3) . ?
C1' H1'A 0.9500 . ?
C1' C2' 1.373(4) . ?
C2' C3' 1.457(4) . ?
C2' C5' 1.437(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.370(4) . ?
C6' H6' 0.9500 . ?

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
C1 S1 C6 93.68(13) . . ?
C3 N1 H1 119.3(19) . . ?
C4 N1 H1 116.1(19) . . ?
C4 N1 C3 124.2(2) . . ?
C4 N2 C5 115.4(2) . . ?
S1 C1 H1A 117.4(16) . . ?
C2 C1 S1 110.7(2) . . ?
C2 C1 H1A 131.8(16) . . ?
C1 C2 C3 127.5(2) . . ?
C1 C2 C5 112.6(2) . . ?
C5 C2 C3 119.8(2) . . ?
O1 C3 N1 121.3(2) . . ?
O1 C3 C2 126.5(3) . . ?
N1 C3 C2 112.2(2) . . ?
N1 C4 H4 117.0 . . ?
N2 C4 N1 126.0(2) . . ?
N2 C4 H4 117.0 . . ?
N2 C5 C2 122.2(2) . . ?
C6 C5 N2 125.0(2) . . ?
C6 C5 C2 112.7(2) . . ?
S1 C6 H6 124.9 . . ?
C5 C6 S1 110.3(2) . . ?
C5 C6 H6 124.9 . . ?
C1' S1' C6' 93.52(13) . . ?
C3' N1' H1' 115.5(18) . . ?
C3' N1' C4' 124.5(2) . . ?
C4' N1' H1' 120.0(18) . . ?
C4' N2' C5' 114.7(2) . . ?
S1' C1' H1'A 124.8 . . ?
C2' C1' S1' 110.5(2) . . ?
C2' C1' H1'A 124.8 . . ?
C1' C2' C3' 127.8(2) . . ?
C1' C2' C5' 113.0(2) . . ?
C5' C2' C3' 119.2(2) . . ?
O1' C3' N1' 121.2(2) . . ?
O1' C3' C2' 125.9(2) . . ?
N1' C3' C2' 112.8(2) . . ?
N1' C4' H4' 117.0 . . ?
N2' C4' N1' 126.0(3) . . ?
N2' C4' H4' 117.0 . . ?
N2' C5' C2' 122.9(2) . . ?
C6' C5' N2' 125.6(2) . . ?
C6' C5' C2' 111.6(2) . . ?
S1' C6' H6' 124.3 . . ?
C5' C6' S1' 111.4(2) . . ?
C5' C6' H6' 124.3 . . ?

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
N1 H1 O1' 0.869(17) 1.945(18) 2.791(3) 164(3) . yes
N1' H1' N2 0.869(17) 1.990(18) 2.849(3) 170(3) 3_656 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_tor_this_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2091575'
loop_
_audit_author_name
_audit_author_address
'Jake Bailey'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 S2'
_chemical_formula_sum            'C6 H4 N2 S2'
_chemical_formula_weight         168.23
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.523(5)
_cell_length_b                   9.208(4)
_cell_length_c                   7.108(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.375(15)
_cell_angle_gamma                90
_cell_volume                     677.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.410
_cell_measurement_theta_min      2.967
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0719 before and 0.0330 after correction. The Ratio of minimum to maximum transmission is 0.8657. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1247
_reflns_number_total             1385
_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       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.065
_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)+(0.0367P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0704
_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), C1(H1A), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.06548(4) 0.85885(4) 0.40237(5) 0.01954(13) Uani 1 1 d . . . . .
S1 S 0.24129(4) 0.36423(4) 0.50776(6) 0.02400(14) Uani 1 1 d . . . . .
N1 N 0.42168(11) 0.55004(14) 0.67298(17) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.468961 0.472829 0.709757 0.020 Uiso 1 1 calc R . . . .
N2 N 0.41825(11) 0.80777(14) 0.68075(18) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.23046(14) 0.66333(16) 0.5212(2) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.29240(14) 0.79951(16) 0.5773(2) 0.0152(3) Uani 1 1 d . . . . .
C1 C 0.47434(14) 0.68347(16) 0.7224(2) 0.0169(3) Uani 1 1 d . . . . .
H1A H 0.559817 0.685315 0.793814 0.020 Uiso 1 1 calc R . . . .
C2 C 0.29949(14) 0.52884(16) 0.5694(2) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.10584(14) 0.68032(16) 0.4243(2) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.049910 0.602636 0.376229 0.021 Uiso 1 1 calc R . . . .
C5 C 0.21310(15) 0.91628(17) 0.5206(2) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.236993 1.015049 0.543799 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C4 1.6979(16) . ?
S2 C5 1.7113(17) . ?
S1 C2 1.6636(16) . ?
N1 H1 0.8800 . ?
N1 C1 1.367(2) . ?
N1 C2 1.3757(19) . ?
N2 C6 1.3963(19) . ?
N2 C1 1.297(2) . ?
C3 C6 1.436(2) . ?
C3 C2 1.445(2) . ?
C3 C4 1.376(2) . ?
C6 C5 1.376(2) . ?
C1 H1A 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?

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
C4 S2 C5 93.68(8) . . ?
C1 N1 H1 117.9 . . ?
C1 N1 C2 124.16(12) . . ?
C2 N1 H1 117.9 . . ?
C1 N2 C6 114.93(13) . . ?
C6 C3 C2 119.90(13) . . ?
C4 C3 C6 112.56(13) . . ?
C4 C3 C2 127.53(14) . . ?
N2 C6 C3 122.27(13) . . ?
C5 C6 N2 125.40(14) . . ?
C5 C6 C3 112.32(14) . . ?
N1 C1 H1A 117.0 . . ?
N2 C1 N1 125.97(13) . . ?
N2 C1 H1A 117.0 . . ?
N1 C2 S1 122.31(11) . . ?
N1 C2 C3 112.75(13) . . ?
C3 C2 S1 124.93(12) . . ?
S2 C4 H4 124.6 . . ?
C3 C4 S2 110.87(11) . . ?
C3 C4 H4 124.6 . . ?
S2 C5 H5 124.7 . . ?
C6 C5 S2 110.57(12) . . ?
C6 C5 H5 124.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
