# 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_2_DBAHMeTzS
_database_code_depnum_ccdc_archive 'CCDC 2084096'
loop_
_audit_author_name
_audit_author_address
'Olivier Renier'
;Stockholm University
Sweden
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2_DBAHMeTzS         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: High angle data are absent due to poor crystal quality 
;
_vrf_PLAT089_2_DBAHMeTzS         
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.12 Note
RESPONSE: High angle data are absent due to poor crystal quality 
;
_vrf_PLAT213_2_DBAHMeTzS         
;
PROBLEM: Atom C5              has ADP max/min Ratio .....        4.1 prolat
RESPONSE: Poor crystal quality and twinning
;
_vrf_PLAT340_2_DBAHMeTzS         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01783 Ang.
RESPONSE: Poor crystal quality
;
# Added during the CSD deposition process: Monday 17 May 2021 08:49 AM
# end Validation Reply Form

_audit_creation_date             2021-05-17
_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         'C2 H3 N4 S, C8 H20 N'
_chemical_formula_sum            'C10 H23 N5 S'
_chemical_formula_weight         245.39
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.089(3)
_cell_length_b                   11.287(3)
_cell_length_c                   13.926(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1428.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1214
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.273
_cell_measurement_theta_min      5.04
_shelx_estimated_absorpt_T_max   0.601
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1201 before and 0.0916 after correction. The Ratio of minimum to maximum transmission is 0.6476. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1739
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        36.369
_diffrn_reflns_theta_max         36.369
_diffrn_reflns_theta_min         5.044
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                591
_reflns_number_total             665
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.35(8)
_refine_ls_extinction_coef       0.0035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.082
_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)+(0.0586P)²+0.2328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.65(8)
 0.35(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(N5) = Uanis(C1)
Uanis(N1) = Uanis(C2)
Uanis(C8) = Uanis(C7)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C1(H1C,H1D,H1E), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C10(H10A,
 H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2451(3) 0.6389(3) 0.4155(2) 0.0325(15) Uani 1 1 d . . . . .
N1 N 0.0211(9) 0.3848(8) 0.4584(7) 0.017(2) Uani 1 1 d . . . . .
H1A H 0.003600 0.307920 0.474484 0.020 Uiso 1 1 calc R U . . .
H1B H 0.119843 0.397351 0.461497 0.020 Uiso 1 1 calc R U . . .
N5 N 0.5119(14) 0.5358(11) 0.4454(7) 0.024(3) Uani 1 1 d . . . . .
N3 N 0.4583(18) 0.3619(11) 0.4855(6) 0.024(3) Uani 1 1 d . . . . .
N4 N 0.5706(15) 0.4294(13) 0.4721(7) 0.028(4) Uani 1 1 d . . . . .
N2 N 0.3301(13) 0.4185(12) 0.4684(7) 0.024(3) Uani 1 1 d . . . . .
C5 C 0.0310(16) 0.4695(12) 0.6227(9) 0.026(4) Uani 1 1 d . . . . .
H5 H 0.126789 0.509350 0.608596 0.032 Uiso 1 1 calc R U . . .
C2 C 0.3646(17) 0.5312(12) 0.4439(8) 0.017(2) Uani 1 1 d . . . . .
C6 C 0.0696(15) 0.3510(12) 0.2808(8) 0.030(4) Uani 1 1 d . . . . .
H6 H 0.168869 0.388088 0.288468 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0315(14) 0.4068(10) 0.3575(9) 0.025(4) Uani 1 1 d . . . . .
H4A H -0.037278 0.493305 0.346326 0.030 Uiso 1 1 calc R U . . .
H4B H -0.131904 0.373900 0.350224 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0893(15) 0.2224(11) 0.2918(8) 0.058(5) Uani 1 1 d . . . . .
H9A H -0.004457 0.182224 0.279901 0.087 Uiso 1 1 calc R U . . .
H9B H 0.122617 0.204997 0.357279 0.087 Uiso 1 1 calc R U . . .
H9C H 0.162991 0.194375 0.245755 0.087 Uiso 1 1 calc R U . . .
C1 C 0.6046(10) 0.6380(9) 0.4242(7) 0.024(3) Uani 1 1 d . . . . .
H1C H 0.707299 0.618974 0.439243 0.036 Uiso 1 1 calc R U . . .
H1D H 0.572821 0.705626 0.463129 0.036 Uiso 1 1 calc R U . . .
H1E H 0.596095 0.658019 0.355953 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0138(13) 0.3850(10) 0.1811(8) 0.040(3) Uani 1 1 d . . . . .
H8A H 0.080471 0.353113 0.132206 0.061 Uiso 1 1 calc R U . . .
H8B H 0.009918 0.471487 0.175573 0.061 Uiso 1 1 calc R U . . .
H8C H -0.084986 0.352165 0.171509 0.061 Uiso 1 1 calc R U . . .
C3 C -0.0546(15) 0.4640(10) 0.5282(10) 0.029(4) Uani 1 1 d . . . . .
H3A H -0.155245 0.434018 0.540443 0.034 Uiso 1 1 calc R U . . .
H3B H -0.062904 0.544586 0.500643 0.034 Uiso 1 1 calc R U . . .
C7 C -0.0514(15) 0.5484(9) 0.6928(8) 0.040(3) Uani 1 1 d . . . . .
H7A H -0.062906 0.627575 0.664894 0.061 Uiso 1 1 calc R U . . .
H7B H 0.004238 0.554126 0.752881 0.061 Uiso 1 1 calc R U . . .
H7C H -0.148596 0.514433 0.705747 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0672(14) 0.3493(11) 0.6670(7) 0.041(4) Uani 1 1 d . . . . .
H10A H 0.135456 0.306498 0.625004 0.062 Uiso 1 1 calc R U . . .
H10B H -0.023400 0.303183 0.674501 0.062 Uiso 1 1 calc R U . . .
H10C H 0.112957 0.361059 0.730051 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.678(14) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C4 1.506(12) . ?
N1 C3 1.488(12) . ?
N5 N4 1.365(13) . ?
N5 C2 1.340(13) . ?
N5 C1 1.459(12) . ?
N3 N4 1.288(11) . ?
N3 N2 1.350(12) . ?
N2 C2 1.354(13) . ?
C5 H5 1.0000 . ?
C5 C3 1.531(15) . ?
C5 C7 1.518(12) . ?
C5 C10 1.526(14) . ?
C6 H6 1.0000 . ?
C6 C4 1.544(13) . ?
C6 C9 1.470(13) . ?
C6 C8 1.527(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 108.0 . . ?
C4 N1 H1A 109.4 . . ?
C4 N1 H1B 109.4 . . ?
C3 N1 H1A 109.4 . . ?
C3 N1 H1B 109.4 . . ?
C3 N1 C4 111.3(9) . . ?
N4 N5 C1 121.7(14) . . ?
C2 N5 N4 111.2(12) . . ?
C2 N5 C1 127.2(13) . . ?
N4 N3 N2 112.3(14) . . ?
N3 N4 N5 104.5(14) . . ?
N3 N2 C2 106.8(12) . . ?
C3 C5 H5 106.9 . . ?
C7 C5 H5 106.9 . . ?
C7 C5 C3 109.0(11) . . ?
C7 C5 C10 111.6(10) . . ?
C10 C5 H5 106.9 . . ?
C10 C5 C3 114.9(10) . . ?
N5 C2 S1 128.5(13) . . ?
N5 C2 N2 105.3(12) . . ?
N2 C2 S1 126.2(14) . . ?
C4 C6 H6 107.0 . . ?
C9 C6 H6 107.0 . . ?
C9 C6 C4 113.7(10) . . ?
C9 C6 C8 112.6(11) . . ?
C8 C6 H6 107.0 . . ?
C8 C6 C4 109.2(10) . . ?
N1 C4 C6 112.9(9) . . ?
N1 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C6 C4 H4A 109.0 . . ?
C6 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C1 H1C 109.5 . . ?
N5 C1 H1D 109.5 . . ?
N5 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C3 C5 110.5(10) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C5 C3 H3A 109.5 . . ?
C5 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 C2 S1 -180.0(8) . . . . ?
N3 N2 C2 N5 1.4(12) . . . . ?
N4 N5 C2 S1 -179.8(8) . . . . ?
N4 N5 C2 N2 -1.2(14) . . . . ?
N4 N3 N2 C2 -1.2(11) . . . . ?
N2 N3 N4 N5 0.4(11) . . . . ?
C2 N5 N4 N3 0.5(13) . . . . ?
C4 N1 C3 C5 -162.2(9) . . . . ?
C9 C6 C4 N1 57.2(14) . . . . ?
C1 N5 N4 N3 179.5(9) . . . . ?
C1 N5 C2 S1 1.3(19) . . . . ?
C1 N5 C2 N2 179.9(10) . . . . ?
C8 C6 C4 N1 -176.1(9) . . . . ?
C3 N1 C4 C6 165.4(10) . . . . ?
C7 C5 C3 N1 -178.6(9) . . . . ?
C10 C5 C3 N1 -52.4(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.65(8)
2 0.35(8)

####################################################################### 
# 
# 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_4_DBAHPhTzS
_database_code_depnum_ccdc_archive 'CCDC 2084098'
loop_
_audit_author_name
_audit_author_address
'Olivier Renier'
;Stockholm University
Sweden
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_4_DBAHPhTzS         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: High angle data are absent due to poor crystal quality 
;
_vrf_PLAT088_4_DBAHPhTzS         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.88 Note
RESPONSE: High angle data are absent due to poor crystal quality 
;
# Added during the CSD deposition process: Monday 17 May 2021 08:49 AM
# end Validation Reply Form

_audit_creation_date             2021-05-17
_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         'C7 H5 N4 S, C8 H20 N'
_chemical_formula_sum            'C15 H25 N5 S'
_chemical_formula_weight         307.46
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   9.1606(16)
_cell_length_b                   17.221(3)
_cell_length_c                   21.778(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3435.6(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4741
_cell_measurement_temperature    100
_cell_measurement_theta_max      44.489
_cell_measurement_theta_min      4.060
_shelx_estimated_absorpt_T_max   0.633
_shelx_estimated_absorpt_T_min   0.488
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.5660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0987 after correction. The Ratio of minimum to maximum transmission is 0.7559. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6816
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        44.557
_diffrn_reflns_theta_max         44.557
_diffrn_reflns_theta_min         4.060
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_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                1210
_reflns_number_total             1349
_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, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0584
_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)+(0.0920P)²+7.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1574
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42552(13) 0.73579(7) 0.32769(5) 0.0247(7) Uani 1 1 d . . . . .
N5 N 0.4904(4) 0.6393(2) 0.42428(18) 0.0191(12) Uani 1 1 d . . . . .
N1 N 0.9591(4) 0.6919(2) 0.31895(16) 0.0207(12) Uani 1 1 d . . . . .
H1A H 0.861699 0.683535 0.323921 0.025 Uiso 1 1 calc R . . . .
H1B H 0.975915 0.700391 0.278317 0.025 Uiso 1 1 calc R . . . .
N2 N 0.6740(5) 0.6602(2) 0.36495(18) 0.0258(12) Uani 1 1 d . . . . .
N4 N 0.6063(5) 0.5992(2) 0.44841(19) 0.0278(12) Uani 1 1 d . . . . .
N3 N 0.7148(5) 0.6125(2) 0.4125(2) 0.0294(13) Uani 1 1 d . . . . .
C1 C 0.3526(6) 0.6359(3) 0.4557(2) 0.0175(13) Uani 1 1 d . . . . .
C7 C 0.5331(6) 0.6776(3) 0.3722(2) 0.0208(13) Uani 1 1 d . . . . .
C6 C 0.2768(5) 0.7035(3) 0.4681(2) 0.0193(13) Uani 1 1 d . . . . .
H6 H 0.312928 0.752083 0.454238 0.023 Uiso 1 1 calc R . . . .
C5 C 0.1479(6) 0.6996(3) 0.5010(2) 0.0230(14) Uani 1 1 d . . . . .
H5 H 0.094557 0.745725 0.509294 0.028 Uiso 1 1 calc R . . . .
C8 C 1.0409(5) 0.6215(3) 0.3389(2) 0.0242(14) Uani 1 1 d . . . . .
H8A H 1.033586 0.617274 0.384173 0.029 Uiso 1 1 calc R . . . .
H8B H 1.145286 0.628807 0.328659 0.029 Uiso 1 1 calc R . . . .
C2 C 0.3024(6) 0.5648(3) 0.4766(2) 0.0211(14) Uani 1 1 d . . . . .
H2 H 0.355739 0.518717 0.468249 0.025 Uiso 1 1 calc R . . . .
C9 C 1.0026(6) 0.7623(3) 0.3545(2) 0.0304(15) Uani 1 1 d . . . . .
H9A H 1.110392 0.763049 0.357774 0.036 Uiso 1 1 calc R . . . .
H9B H 0.963145 0.757399 0.396660 0.036 Uiso 1 1 calc R . . . .
C3 C 0.1741(6) 0.5615(3) 0.5097(2) 0.0257(14) Uani 1 1 d . . . . .
H3 H 0.138788 0.513032 0.524193 0.031 Uiso 1 1 calc R . . . .
C4 C 0.0966(5) 0.6292(3) 0.5218(2) 0.0276(15) Uani 1 1 d . . . . .
H4 H 0.008047 0.626825 0.544435 0.033 Uiso 1 1 calc R . . . .
C13 C 0.7922(5) 0.8438(3) 0.3153(3) 0.0352(16) Uani 1 1 d . . . . .
H13A H 0.769398 0.895186 0.298570 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.736936 0.835587 0.353273 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.765469 0.803819 0.285266 0.053 Uiso 1 1 calc GR . . . .
C15 C 1.0031(6) 0.9020(3) 0.3738(3) 0.0495(17) Uani 1 1 d . . . . .
H15A H 1.108893 0.898518 0.379884 0.074 Uiso 1 1 calc GR . . . .
H15B H 0.953375 0.894841 0.413234 0.074 Uiso 1 1 calc GR . . . .
H15C H 0.978490 0.953178 0.357017 0.074 Uiso 1 1 calc GR . . . .
C11 C 0.9538(6) 0.8387(3) 0.3288(2) 0.0335(15) Uani 1 1 d . . . . .
H11 H 1.007200 0.847038 0.289272 0.040 Uiso 1 1 calc R . . . .
C14 C 1.0814(7) 0.4801(3) 0.3380(3) 0.0543(19) Uani 1 1 d . . . . .
H14A H 1.182529 0.484790 0.323794 0.081 Uiso 1 1 calc GR . . . .
H14B H 1.041010 0.430311 0.324438 0.081 Uiso 1 1 calc GR . . . .
H14C H 1.078935 0.482798 0.382944 0.081 Uiso 1 1 calc GR . . . .
C12 C 0.9520(13) 0.5389(4) 0.2512(5) 0.120(4) Uani 1 1 d . . . . .
H12A H 0.875215 0.576520 0.241470 0.144 Uiso 1 1 calc GR . . . .
H12B H 0.915730 0.486173 0.243775 0.144 Uiso 1 1 calc GR . . . .
H12C H 1.037261 0.548624 0.225125 0.48(18) Uiso 1 1 calc GR . . . .
C10 C 0.9908(9) 0.5462(4) 0.3113(3) 0.079(3) Uani 1 1 d . . . . .
H10 H 0.895002 0.538371 0.332450 0.095 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 C7 1.707(5) . ?
N5 N4 1.371(5) . ?
N5 C1 1.437(6) . ?
N5 C7 1.371(6) . ?
N1 C8 1.491(6) . ?
N1 C9 1.493(6) . ?
N2 N3 1.373(5) . ?
N2 C7 1.334(6) . ?
N4 N3 1.286(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.385(6) . ?
C6 C5 1.382(7) . ?
C5 C4 1.378(6) . ?
C8 C10 1.500(8) . ?
C2 C3 1.379(6) . ?
C9 C11 1.497(7) . ?
C3 C4 1.389(7) . ?
C13 C11 1.512(7) . ?
C15 C11 1.535(7) . ?
C14 C10 1.524(8) . ?
C12 C10 1.362(10) . ?

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
N4 N5 C1 118.5(4) . . ?
C7 N5 N4 109.8(4) . . ?
C7 N5 C1 131.7(4) . . ?
C8 N1 C9 112.0(4) . . ?
C7 N2 N3 108.0(4) . . ?
N3 N4 N5 106.0(4) . . ?
N4 N3 N2 110.8(4) . . ?
C6 C1 N5 120.1(4) . . ?
C6 C1 C2 120.8(5) . . ?
C2 C1 N5 119.0(4) . . ?
N5 C7 S1 126.0(4) . . ?
N2 C7 S1 128.6(4) . . ?
N2 C7 N5 105.4(4) . . ?
C1 C6 C5 119.4(4) . . ?
C4 C5 C6 120.3(5) . . ?
N1 C8 C10 115.6(4) . . ?
C3 C2 C1 119.4(4) . . ?
N1 C9 C11 116.0(4) . . ?
C2 C3 C4 120.0(5) . . ?
C5 C4 C3 120.1(5) . . ?
C9 C11 C13 114.6(4) . . ?
C9 C11 C15 107.3(4) . . ?
C13 C11 C15 111.8(4) . . ?
C8 C10 C14 109.0(5) . . ?
C12 C10 C8 123.1(6) . . ?
C12 C10 C14 116.0(6) . . ?

_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_5_Et3NHMeDiTS
_database_code_depnum_ccdc_archive 'CCDC 2084100'
loop_
_audit_author_name
_audit_author_address
'Olivier Renier'
;Stockholm University
Sweden
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_5_Et3NHMeDiTS       
;
PROBLEM: Hirshfeld Test Diff for    S2       --C1       .        8.0 s.u.
RESPONSE: High angle data are absent due to poor crystal quality 
;
# Added during the CSD deposition process: Monday 17 May 2021 08:49 AM
# end Validation Reply Form

_audit_creation_date             2021-05-17
_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         'C3 H3 N2 S2, C6 H16 N'
_chemical_formula_sum            'C9 H19 N3 S2'
_chemical_formula_weight         233.39
_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      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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.9568(6)
_cell_length_b                   13.7361(7)
_cell_length_c                   16.5427(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2489.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1099 before and 0.0550 after correction. The Ratio of minimum to maximum transmission is 0.9281. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.996
_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       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20106
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.462
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_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_source_current           1.4
_diffrn_source_power             0.07
_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                2319
_reflns_number_total             2534
_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, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.153
_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)+(0.0148P)²+1.5824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C4(H4A,H4B), C6(H6A,H6B)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71528(3) 0.61204(3) 0.27401(2) 0.01650(10) Uani 1 1 d . . . . .
S2 S 0.48819(3) 0.70737(3) 0.34227(2) 0.02285(11) Uani 1 1 d . . . . .
N1 N 0.57844(11) 0.68739(8) 0.56830(7) 0.0135(2) Uani 1 1 d . . . . .
H1 H 0.6153(16) 0.6683(13) 0.5212(11) 0.025(5) Uiso 1 1 d . . . . .
N2 N 0.78364(11) 0.57378(9) 0.41738(7) 0.0160(3) Uani 1 1 d . . . . .
N3 N 0.67416(11) 0.62347(9) 0.42487(7) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.38554(14) 0.64893(12) 0.64618(10) 0.0239(3) Uani 1 1 d . . . . .
H9A H 0.432226 0.651958 0.696650 0.036 Uiso 1 1 calc R U . . .
H9B H 0.320979 0.599928 0.651231 0.036 Uiso 1 1 calc R U . . .
H9C H 0.348868 0.712660 0.635251 0.036 Uiso 1 1 calc R U . . .
C8 C 0.46992(13) 0.62147(11) 0.57721(9) 0.0190(3) Uani 1 1 d . . . . .
H8A H 0.499174 0.554076 0.585842 0.023 Uiso 1 1 calc R U . . .
H8B H 0.422837 0.622344 0.526135 0.023 Uiso 1 1 calc R U . . .
C4 C 0.54048(14) 0.79162(10) 0.55873(9) 0.0189(3) Uani 1 1 d . . . . .
H4A H 0.520914 0.819019 0.612542 0.023 Uiso 1 1 calc R U . . .
H4B H 0.465600 0.794577 0.525323 0.023 Uiso 1 1 calc R U . . .
C5 C 0.63910(17) 0.85303(11) 0.51942(10) 0.0277(4) Uani 1 1 d . . . . .
H5A H 0.711998 0.853188 0.553750 0.041 Uiso 1 1 calc R U . . .
H5B H 0.609477 0.919866 0.512734 0.041 Uiso 1 1 calc R U . . .
H5C H 0.659533 0.825710 0.466398 0.041 Uiso 1 1 calc R U . . .
C7 C 0.73673(16) 0.57925(13) 0.63050(10) 0.0285(4) Uani 1 1 d . . . . .
H7A H 0.678061 0.526314 0.638710 0.043 Uiso 1 1 calc R U . . .
H7B H 0.799287 0.576703 0.672786 0.043 Uiso 1 1 calc R U . . .
H7C H 0.775420 0.572084 0.577424 0.043 Uiso 1 1 calc R U . . .
C6 C 0.67100(13) 0.67595(11) 0.63449(9) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.629561 0.681727 0.687452 0.022 Uiso 1 1 calc R U . . .
H6B H 0.731549 0.729237 0.630541 0.022 Uiso 1 1 calc R U . . .
C3 C 0.92769(13) 0.50585(11) 0.31851(9) 0.0196(3) Uani 1 1 d . . . . .
H3A H 0.982678 0.499864 0.364964 0.029 Uiso 1 1 calc R U . . .
H3B H 0.969458 0.540475 0.274715 0.029 Uiso 1 1 calc R U . . .
H3C H 0.903981 0.440831 0.299857 0.029 Uiso 1 1 calc R U . . .
C2 C 0.81643(12) 0.56128(10) 0.34285(9) 0.0143(3) Uani 1 1 d . . . . .
C1 C 0.62337(13) 0.64829(10) 0.35517(9) 0.0155(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7353(14) . ?
S1 C1 1.7506(14) . ?
S2 C1 1.7023(15) . ?
N1 H1 0.916(19) . ?
N1 C8 1.5018(18) . ?
N1 C4 1.4993(18) . ?
N1 C6 1.5006(18) . ?
N2 N3 1.3858(16) . ?
N2 C2 1.2955(18) . ?
N3 C1 1.3249(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.516(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.517(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.512(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C2 1.4927(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 88.76(7) . . ?
C8 N1 H1 105.1(11) . . ?
C4 N1 H1 107.8(11) . . ?
C4 N1 C8 111.49(11) . . ?
C4 N1 C6 111.38(11) . . ?
C6 N1 H1 107.0(11) . . ?
C6 N1 C8 113.60(11) . . ?
C2 N2 N3 112.98(12) . . ?
C1 N3 N2 114.36(12) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
N1 C8 C9 113.99(12) . . ?
N1 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.6 . . ?
N1 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
N1 C4 C5 112.25(12) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
N1 C6 C7 112.45(12) . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
N2 C2 S1 113.22(11) . . ?
N2 C2 C3 123.42(13) . . ?
C3 C2 S1 123.33(11) . . ?
S2 C1 S1 122.69(9) . . ?
N3 C1 S1 110.65(10) . . ?
N3 C1 S2 126.67(11) . . ?

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
N2 N3 C1 S1 -1.53(15) . . . . ?
N2 N3 C1 S2 178.59(10) . . . . ?
N3 N2 C2 S1 1.01(15) . . . . ?
N3 N2 C2 C3 -177.00(12) . . . . ?
C8 N1 C4 C5 -158.71(13) . . . . ?
C8 N1 C6 C7 69.17(16) . . . . ?
C4 N1 C8 C9 -55.93(17) . . . . ?
C4 N1 C6 C7 -163.93(13) . . . . ?
C6 N1 C8 C9 70.91(16) . . . . ?
C6 N1 C4 C5 73.24(16) . . . . ?
C2 S1 C1 S2 -178.42(10) . . . . ?
C2 S1 C1 N3 1.70(11) . . . . ?
C2 N2 N3 C1 0.37(17) . . . . ?
C1 S1 C2 N2 -1.55(11) . . . . ?
C1 S1 C2 C3 176.46(13) . . . . ?

_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_6_DBAHMeDiTS
_database_code_depnum_ccdc_archive 'CCDC 2084099'
loop_
_audit_author_name
_audit_author_address
'Olivier Renier'
;Stockholm University
Sweden
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT109_6_DBAHMeDiTS        
;
PROBLEM: Twinning Matrix is inverted Laue group operation          ? Check
RESPONSE: Checked but no twinning has been detected
;
# Added during the CSD deposition process: Monday 17 May 2021 08:49 AM
# end Validation Reply Form

_audit_creation_date             2021-05-17
_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         'C3 H3 N2 S2, 0.5(C8 H20.463 N), 0.5(C8 H20 N)'
_chemical_formula_sum            'C11 H23.23 N3 S2'
_chemical_formula_weight         261.68
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.8848(14)
_cell_length_b                   6.9574(4)
_cell_length_c                   23.6250(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2939.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9214
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1056 before and 0.0784 after correction. The Ratio of minimum to maximum transmission is 0.8526. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1138
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27448
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.583
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6754
_reflns_number_total             8128
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Flack x determined using 2366 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.097
_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)+(0.0131P)²+4.8729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.73(13)
 0.27(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
3. Others
 Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(H8AA)=Sof(H8AB)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=Sof(C11)=Sof(H11)=1-FVAR(1)
 Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C10)=Sof(H8BC)=Sof(H8BD)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C19(H19), C18(H18), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N1'(H1'A,H1'B), C8(H8BC,H8BD), C8(H8AA,H8AB), C7(H7A,H7B),
 C17(H17A,H17B), C16(H16A,H16B)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12D,H12E,H12F), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C13(H13D,H13E,H13F), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C3(H3A,
 H3B,H3C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S4 S 0.56186(7) 0.19988(16) 0.66361(6) 0.0219(3) Uani 1 1 d . . . . .
S3 S 0.43054(6) 0.13626(15) 0.58278(5) 0.0178(2) Uani 1 1 d . . . . .
S2 S 0.81121(7) 0.18580(16) 0.33748(6) 0.0235(3) Uani 1 1 d . . . . .
S1 S 0.67837(6) 0.11456(15) 0.41552(5) 0.0169(2) Uani 1 1 d . . . . .
N2' N 0.4204(2) 0.5010(6) 0.57306(18) 0.0201(9) Uani 1 1 d . . . . .
N1 N 0.8161(2) 0.7200(5) 0.3337(2) 0.0132(8) Uani 1 1 d . . . . .
H1A H 0.787803 0.641476 0.355787 0.016 Uiso 1 1 calc R U . . .
H1B H 0.804327 0.843645 0.342442 0.016 Uiso 1 1 calc R U . . .
N2 N 0.6686(2) 0.4766(6) 0.42919(17) 0.0191(9) Uani 1 1 d . . . . .
N3 N 0.7284(2) 0.4477(5) 0.39261(17) 0.0160(8) Uani 1 1 d . . . . .
N1' N 0.5669(2) 0.7321(5) 0.6681(2) 0.0130(8) Uani 1 1 d . . . . .
H1'A H 0.539228 0.644982 0.648408 0.016 Uiso 1 1 calc R U . . .
H1'B H 0.553160 0.851520 0.656272 0.016 Uiso 1 1 calc R U . . .
C4 C 0.4933(3) 0.2832(6) 0.6203(2) 0.0148(10) Uani 1 1 d . . . . .
C5 C 0.3896(3) 0.3430(7) 0.5559(2) 0.0194(10) Uani 1 1 d . . . . .
C6 C 0.3243(3) 0.3419(8) 0.5158(3) 0.0313(13) Uani 1 1 d . . . . .
H6A H 0.305150 0.473027 0.511443 0.047 Uiso 1 1 calc R U . . .
H6B H 0.284741 0.259130 0.530988 0.047 Uiso 1 1 calc R U . . .
H6C H 0.340450 0.292821 0.478915 0.047 Uiso 1 1 calc R U . . .
N3' N 0.4796(2) 0.4665(5) 0.60993(17) 0.0154(8) Uani 1 1 d . . . . .
C12 C 0.7069(4) 0.6761(10) 0.1949(3) 0.0386(16) Uani 1 1 d . . . . .
H12D H 0.749861 0.616731 0.175939 0.058 Uiso 0.537(18) 1 calc R U P A 2
H12E H 0.704964 0.813077 0.185420 0.058 Uiso 0.537(18) 1 calc R U P A 2
H12F H 0.660789 0.613318 0.182324 0.058 Uiso 0.537(18) 1 calc R U P A 2
H12A H 0.739876 0.723962 0.164910 0.058 Uiso 0.463(18) 1 calc R U P A 1
H12B H 0.655039 0.709627 0.186031 0.058 Uiso 0.463(18) 1 calc R U P A 1
H12C H 0.711708 0.536033 0.197636 0.058 Uiso 0.463(18) 1 calc R U P A 1
C10 C 0.7153(5) 0.6522(12) 0.2604(3) 0.010(2) Uani 0.537(18) 1 d . . P A 2
H10 H 0.704497 0.514210 0.269061 0.012 Uiso 1 1 calc R U . A 2
C8 C 0.7979(3) 0.6835(7) 0.2729(2) 0.0181(10) Uani 1 1 d . . . . .
H8BC H 0.825978 0.568738 0.260162 0.022 Uiso 0.537(18) 1 calc R U P A 2
H8BD H 0.815637 0.794229 0.250220 0.022 Uiso 0.537(18) 1 calc R U P A 2
H8AA H 0.839842 0.731996 0.249535 0.022 Uiso 0.463(18) 1 calc R U P A 1
H8AB H 0.795076 0.542811 0.267057 0.022 Uiso 0.463(18) 1 calc R U P A 1
C7 C 0.8972(3) 0.6858(6) 0.3463(2) 0.0165(9) Uani 1 1 d . . . . .
H7A H 0.927865 0.750981 0.317176 0.020 Uiso 1 1 calc R U . . .
H7B H 0.907552 0.546261 0.343836 0.020 Uiso 1 1 calc R U . . .
C9 C 0.9206(3) 0.7571(7) 0.4040(2) 0.0214(10) Uani 1 1 d . . . . .
H9 H 0.913445 0.899597 0.405364 0.026 Uiso 1 1 calc R U . . .
C15 C 0.8759(4) 0.6665(9) 0.4521(2) 0.0360(14) Uani 1 1 d . . . . .
H15A H 0.823099 0.702296 0.448353 0.054 Uiso 1 1 calc R U . . .
H15B H 0.895115 0.712533 0.488443 0.054 Uiso 1 1 calc R U . . .
H15C H 0.880643 0.526267 0.450238 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6619(4) 0.7630(11) 0.2914(3) 0.0389(17) Uani 1 1 d . . . . .
H13D H 0.672143 0.900162 0.285836 0.058 Uiso 0.537(18) 1 calc R U P A 2
H13E H 0.665563 0.731748 0.331705 0.058 Uiso 0.537(18) 1 calc R U P A 2
H13F H 0.611479 0.733325 0.277742 0.058 Uiso 0.537(18) 1 calc R U P A 2
H13A H 0.622287 0.845275 0.276072 0.058 Uiso 0.463(18) 1 calc R U P A 1
H13B H 0.676570 0.809696 0.328893 0.058 Uiso 0.463(18) 1 calc R U P A 1
H13C H 0.643577 0.630740 0.294435 0.058 Uiso 0.463(18) 1 calc R U P A 1
C14 C 1.0038(3) 0.7130(8) 0.4116(3) 0.0351(13) Uani 1 1 d . . . . .
H14A H 1.012524 0.575406 0.405543 0.053 Uiso 1 1 calc R U . . .
H14B H 1.019324 0.748051 0.450007 0.053 Uiso 1 1 calc R U . . .
H14C H 1.032931 0.787141 0.384053 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7410(3) 0.2659(6) 0.3808(2) 0.0130(10) Uani 1 1 d . . . . .
C2 C 0.6374(3) 0.3178(7) 0.4446(2) 0.0186(9) Uani 1 1 d . . . . .
C3 C 0.5707(3) 0.3082(8) 0.4828(3) 0.0303(13) Uani 1 1 d . . . . .
H3A H 0.556589 0.438388 0.494491 0.045 Uiso 1 1 calc R U . . .
H3B H 0.582955 0.231503 0.516359 0.045 Uiso 1 1 calc R U . . .
H3C H 0.528899 0.248337 0.462606 0.045 Uiso 1 1 calc R U . . .
C20 C 0.4593(4) 0.7012(11) 0.8081(3) 0.0423(17) Uani 1 1 d . . . . .
H20A H 0.470434 0.834121 0.818944 0.063 Uiso 1 1 calc R U . . .
H20B H 0.494538 0.614251 0.826885 0.063 Uiso 1 1 calc R U . . .
H20C H 0.408160 0.668963 0.819603 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4669(4) 0.6792(12) 0.7420(3) 0.0433(17) Uani 1 1 d . . . . .
H19 H 0.456258 0.541529 0.732856 0.052 Uiso 1 1 calc R U . . .
C17 C 0.5497(3) 0.7127(7) 0.7297(2) 0.0164(9) Uani 1 1 d . . . . .
H17A H 0.566020 0.831004 0.749453 0.020 Uiso 1 1 calc R U . . .
H17B H 0.578861 0.604001 0.745312 0.020 Uiso 1 1 calc R U . . .
C16 C 0.6474(3) 0.7021(7) 0.6547(2) 0.0169(9) Uani 1 1 d . . . . .
H16A H 0.666093 0.590860 0.676738 0.020 Uiso 1 1 calc R U . . .
H16B H 0.675993 0.816850 0.666816 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6619(3) 0.6660(6) 0.5918(2) 0.0172(9) Uani 1 1 d . . . . .
H18 H 0.636610 0.543075 0.581027 0.021 Uiso 1 1 calc R U . . .
C22 C 0.6311(3) 0.8237(8) 0.5547(2) 0.0274(12) Uani 1 1 d . . . . .
H22A H 0.653274 0.946855 0.565891 0.041 Uiso 1 1 calc R U . . .
H22B H 0.576712 0.830019 0.559154 0.041 Uiso 1 1 calc R U . . .
H22C H 0.643453 0.796724 0.515112 0.041 Uiso 1 1 calc R U . . .
C23 C 0.4131(4) 0.7927(10) 0.7114(4) 0.0399(17) Uani 1 1 d . . . . .
H23A H 0.425200 0.929315 0.715641 0.060 Uiso 1 1 calc R U . . .
H23B H 0.362965 0.768306 0.726623 0.060 Uiso 1 1 calc R U . . .
H23C H 0.414375 0.757760 0.671267 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7456(3) 0.6406(8) 0.5830(3) 0.0324(12) Uani 1 1 d . . . . .
H21A H 0.755645 0.613540 0.542990 0.049 Uiso 1 1 calc R U . . .
H21B H 0.763521 0.533265 0.606189 0.049 Uiso 1 1 calc R U . . .
H21C H 0.771660 0.758642 0.594133 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7294(6) 0.7684(19) 0.2520(5) 0.019(3) Uani 0.463(18) 1 d . . P A 1
H11 H 0.740275 0.906838 0.244157 0.022 Uiso 0.463(18) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S4 C4 1.699(6) . ?
S3 C4 1.758(5) . ?
S3 C5 1.734(5) . ?
S2 C1 1.713(6) . ?
S1 C1 1.742(5) . ?
S1 C2 1.735(5) . ?
N2' C5 1.295(6) . ?
N2' N3' 1.392(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C8 1.494(7) . ?
N1 C7 1.500(6) . ?
N2 N3 1.389(6) . ?
N2 C2 1.290(6) . ?
N3 C1 1.315(6) . ?
N1' H1'A 0.9100 . ?
N1' H1'B 0.9100 . ?
N1' C17 1.495(7) . ?
N1' C16 1.489(6) . ?
C4 N3' 1.322(6) . ?
C5 C6 1.503(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C10 1.564(10) . ?
C12 C11 1.546(13) . ?
C10 H10 1.0000 . ?
C10 C8 1.523(10) . ?
C10 C13 1.428(10) . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 C11 1.448(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C9 1.509(7) . ?
C9 H9 1.0000 . ?
C9 C15 1.525(8) . ?
C9 C14 1.531(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C11 1.524(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C2 C3 1.497(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.576(9) . ?
C19 H19 1.0000 . ?
C19 C17 1.527(9) . ?
C19 C23 1.439(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C18 1.531(7) . ?
C18 H18 1.0000 . ?
C18 C22 1.507(7) . ?
C18 C21 1.523(7) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C11 H11 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S3 C4 88.4(2) . . ?
C2 S1 C1 88.0(2) . . ?
C5 N2' N3' 112.0(4) . . ?
H1A N1 H1B 107.9 . . ?
C8 N1 H1A 109.2 . . ?
C8 N1 H1B 109.2 . . ?
C8 N1 C7 112.1(4) . . ?
C7 N1 H1A 109.2 . . ?
C7 N1 H1B 109.2 . . ?
C2 N2 N3 112.7(4) . . ?
C1 N3 N2 113.8(4) . . ?
H1'A N1' H1'B 107.8 . . ?
C17 N1' H1'A 109.0 . . ?
C17 N1' H1'B 109.0 . . ?
C16 N1' H1'A 109.0 . . ?
C16 N1' H1'B 109.0 . . ?
C16 N1' C17 113.1(4) . . ?
S4 C4 S3 124.5(3) . . ?
N3' C4 S4 125.0(4) . . ?
N3' C4 S3 110.5(4) . . ?
N2' C5 S3 114.2(4) . . ?
N2' C5 C6 122.1(5) . . ?
C6 C5 S3 123.7(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 N3' N2' 115.0(4) . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C12 H12D 109.5 . . ?
C10 C12 H12E 109.5 . . ?
C10 C12 H12F 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C12 C10 H10 106.6 . . ?
C8 C10 C12 105.6(6) . . ?
C8 C10 H10 106.6 . . ?
C13 C10 C12 112.7(6) . . ?
C13 C10 H10 106.6 . . ?
C13 C10 C8 118.2(6) . . ?
N1 C8 C10 114.9(5) . . ?
N1 C8 H8BC 108.5 . . ?
N1 C8 H8BD 108.5 . . ?
N1 C8 H8AA 108.2 . . ?
N1 C8 H8AB 108.2 . . ?
C10 C8 H8BC 108.5 . . ?
C10 C8 H8BD 108.5 . . ?
H8BC C8 H8BD 107.5 . . ?
H8AA C8 H8AB 107.4 . . ?
C11 C8 N1 116.3(6) . . ?
C11 C8 H8AA 108.2 . . ?
C11 C8 H8AB 108.2 . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C9 113.3(4) . . ?
H7A C7 H7B 107.7 . . ?
C9 C7 H7A 108.9 . . ?
C9 C7 H7B 108.9 . . ?
C7 C9 H9 108.6 . . ?
C7 C9 C15 113.0(4) . . ?
C7 C9 C14 108.0(4) . . ?
C15 C9 H9 108.6 . . ?
C15 C9 C14 109.9(5) . . ?
C14 C9 H9 108.6 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C13 H13D 109.5 . . ?
C10 C13 H13E 109.5 . . ?
C10 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S2 C1 S1 123.8(3) . . ?
N3 C1 S2 124.4(4) . . ?
N3 C1 S1 111.8(4) . . ?
N2 C2 S1 113.8(4) . . ?
N2 C2 C3 123.6(4) . . ?
C3 C2 S1 122.6(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C20 C19 H19 106.9 . . ?
C17 C19 C20 104.9(6) . . ?
C17 C19 H19 106.9 . . ?
C23 C19 C20 112.7(6) . . ?
C23 C19 H19 106.9 . . ?
C23 C19 C17 118.0(6) . . ?
N1' C17 C19 113.5(5) . . ?
N1' C17 H17A 108.9 . . ?
N1' C17 H17B 108.9 . . ?
C19 C17 H17A 108.9 . . ?
C19 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N1' C16 H16A 109.0 . . ?
N1' C16 H16B 109.0 . . ?
N1' C16 C18 113.1(4) . . ?
H16A C16 H16B 107.8 . . ?
C18 C16 H16A 109.0 . . ?
C18 C16 H16B 109.0 . . ?
C16 C18 H18 108.1 . . ?
C22 C18 C16 112.5(4) . . ?
C22 C18 H18 108.1 . . ?
C22 C18 C21 111.4(4) . . ?
C21 C18 C16 108.5(4) . . ?
C21 C18 H18 108.1 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C11 H11 106.9 . . ?
C8 C11 C12 110.4(8) . . ?
C8 C11 C13 116.9(8) . . ?
C8 C11 H11 106.9 . . ?
C13 C11 C12 108.5(8) . . ?
C13 C11 H11 106.9 . . ?

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 N3' N2' -179.9(4) . . . . ?
S3 C4 N3' N2' 0.2(6) . . . . ?
N1 C8 C11 C12 -164.7(6) . . . . ?
N1 C8 C11 C13 -40.2(11) . . . . ?
N1 C7 C9 C15 58.0(6) . . . . ?
N1 C7 C9 C14 179.8(4) . . . . ?
N2 N3 C1 S2 -179.4(4) . . . . ?
N2 N3 C1 S1 -0.5(5) . . . . ?
N3 N2 C2 S1 -0.1(5) . . . . ?
N3 N2 C2 C3 -178.5(5) . . . . ?
N1' C16 C18 C22 55.4(5) . . . . ?
N1' C16 C18 C21 179.1(4) . . . . ?
C4 S3 C5 N2' 0.6(4) . . . . ?
C4 S3 C5 C6 -179.9(5) . . . . ?
C5 S3 C4 S4 179.7(4) . . . . ?
C5 S3 C4 N3' -0.4(4) . . . . ?
C5 N2' N3' C4 0.2(6) . . . . ?
N3' N2' C5 S3 -0.5(6) . . . . ?
N3' N2' C5 C6 179.9(5) . . . . ?
C12 C10 C8 N1 164.3(4) . . . . ?
C8 N1 C7 C9 168.9(4) . . . . ?
C7 N1 C8 C10 161.3(5) . . . . ?
C7 N1 C8 C11 -160.9(7) . . . . ?
C13 C10 C8 N1 37.2(9) . . . . ?
C1 S1 C2 N2 -0.1(4) . . . . ?
C1 S1 C2 C3 178.3(5) . . . . ?
C2 S1 C1 S2 179.3(4) . . . . ?
C2 S1 C1 N3 0.3(4) . . . . ?
C2 N2 N3 C1 0.4(6) . . . . ?
C20 C19 C17 N1' -169.9(5) . . . . ?
C17 N1' C16 C18 163.9(4) . . . . ?
C16 N1' C17 C19 -161.6(5) . . . . ?
C23 C19 C17 N1' -43.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.73(13)
2 0.27(13)

####################################################################### 
# 
# 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_oli_3_Et3NHPhTzS
_database_code_depnum_ccdc_archive 'CCDC 2084097'
loop_
_audit_author_name
_audit_author_address
'Olivier Renier'
;Stockholm University
Sweden
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_oli_3_Et3NHPhTzS    
;
PROBLEM: Hirshfeld Test Diff for    N2       --N3       .       14.0 s.u.
RESPONSE: High angle data are absent due to poor crystal quality 
;
# Added during the CSD deposition process: Monday 17 May 2021 08:49 AM
# end Validation Reply Form

_audit_creation_date             2021-05-17
_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         'C7 H5 N4 S, C6 H16 N'
_chemical_formula_sum            'C13 H21 N5 S'
_chemical_formula_weight         279.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/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                   9.0734(9)
_cell_length_b                   13.2194(13)
_cell_length_c                   13.1558(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.249(4)
_cell_angle_gamma                90
_cell_volume                     1507.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9298
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0997 before and 0.0599 after correction. The Ratio of minimum to maximum transmission is 0.9626. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29013
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.236
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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_source_current           1.4
_diffrn_source_power             0.07
_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                2709
_reflns_number_total             3066
_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, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.201
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.854
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0853P)²+3.8134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.1937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-N4
 2.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C11(H11), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.41984(9) 0.31954(6) 0.80065(6) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.0880(3) 0.21527(17) 0.67938(18) 0.0193(5) Uani 1 1 d . . . . .
H1 H 0.178(4) 0.229(3) 0.690(3) 0.022(8) Uiso 1 1 d . . . . .
C4 C -0.1182(4) 0.1070(3) 0.5595(3) 0.0375(8) Uani 1 1 d . . . . .
H4A H -0.144106 0.078200 0.620726 0.056 Uiso 1 1 calc R U . . .
H4B H -0.136427 0.056389 0.502749 0.056 Uiso 1 1 calc R U . . .
H4C H -0.183046 0.166442 0.533531 0.056 Uiso 1 1 calc R U . . .
N2 N 0.3778(3) 0.2643(2) 0.5940(2) 0.0377(7) Uani 1 1 d . . . . .
C1 C 0.0491(3) 0.1379(2) 0.5927(2) 0.0254(6) Uani 1 1 d . . . . .
H1A H 0.113750 0.077132 0.617233 0.031 Uiso 1 1 calc R U . . .
H1B H 0.074854 0.165270 0.530064 0.031 Uiso 1 1 calc R U . . .
C2 C 0.0005(3) 0.3126(2) 0.6497(2) 0.0277(6) Uani 1 1 d . . . . .
H2A H 0.033667 0.359928 0.710570 0.033 Uiso 1 1 calc R U . . .
H2B H -0.110788 0.298820 0.637044 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0221(4) 0.3630(2) 0.5526(3) 0.0357(7) Uani 1 1 d . . . . .
H5A H 0.132617 0.370283 0.561152 0.054 Uiso 1 1 calc R U . . .
H5B H -0.026467 0.429894 0.543779 0.054 Uiso 1 1 calc R U . . .
H5C H -0.025680 0.321532 0.489708 0.054 Uiso 1 1 calc R U . . .
N5 N 0.5774(3) 0.36021(19) 0.65620(19) 0.0250(5) Uani 1 1 d . . . . .
C6 C 0.1669(4) 0.0844(2) 0.8236(3) 0.0347(7) Uani 1 1 d . . . . .
H6A H 0.120237 0.026634 0.778948 0.052 Uiso 1 1 calc R U . . .
H6B H 0.169068 0.071286 0.897331 0.052 Uiso 1 1 calc R U . . .
H6C H 0.272387 0.094482 0.820364 0.052 Uiso 1 1 calc R U . . .
C3 C 0.0730(4) 0.1780(2) 0.7838(2) 0.0277(6) Uani 1 1 d . . . . .
H3A H -0.036979 0.163309 0.775511 0.033 Uiso 1 1 calc R U . . .
H3B H 0.106303 0.232239 0.837651 0.033 Uiso 1 1 calc R U . . .
N3 N 0.4504(4) 0.2832(2) 0.5200(2) 0.0385(7) Uani 1 1 d D . . . .
C7 C 0.4628(3) 0.3140(2) 0.6817(2) 0.0244(6) Uani 1 1 d . . . . .
C8 C 0.7035(3) 0.4211(2) 0.7196(2) 0.0232(6) Uani 1 1 d . . . . .
C13 C 0.7366(3) 0.5084(2) 0.6736(2) 0.0253(6) Uani 1 1 d . . . . .
H13 H 0.672178 0.530262 0.606243 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8668(4) 0.5643(2) 0.7278(3) 0.0376(8) Uani 1 1 d . . . . .
H12 H 0.894216 0.623918 0.697453 0.045 Uiso 1 1 calc R U . . .
C11 C 0.9570(4) 0.5301(3) 0.8291(3) 0.0388(8) Uani 1 1 d . . . . .
H11 H 1.045703 0.566964 0.867840 0.047 Uiso 1 1 calc R U . . .
N4 N 0.5667(4) 0.3390(2) 0.5521(2) 0.0384(7) Uani 1 1 d D . . . .
C9 C 0.7907(3) 0.3879(2) 0.8173(2) 0.0277(6) Uani 1 1 d . . . . .
H9 H 0.764414 0.327473 0.847034 0.033 Uiso 1 1 calc R U . . .
C10 C 0.9156(4) 0.4432(3) 0.8710(3) 0.0344(7) Uani 1 1 d . . . . .
H10 H 0.975988 0.421239 0.939424 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.723(3) . ?
N1 H1 0.81(4) . ?
N1 C1 1.494(3) . ?
N1 C2 1.501(4) . ?
N1 C3 1.504(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C1 1.506(4) . ?
N2 N3 1.350(4) . ?
N2 C7 1.352(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C5 1.505(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N5 C7 1.332(4) . ?
N5 C8 1.444(4) . ?
N5 N4 1.373(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C3 1.505(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N3 N4 1.254(4) . ?
C8 C13 1.377(4) . ?
C8 C9 1.367(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.396(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.415(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.374(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.358(5) . ?
C10 H10 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 N1 H1 106(2) . . ?
C1 N1 C2 113.7(2) . . ?
C1 N1 C3 114.1(2) . . ?
C2 N1 H1 107(2) . . ?
C2 N1 C3 109.5(2) . . ?
C3 N1 H1 106(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
N3 N2 C7 104.4(3) . . ?
N1 C1 C4 113.4(2) . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C4 C1 H1A 108.9 . . ?
C4 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
N1 C2 C5 114.1(2) . . ?
H2A C2 H2B 107.6 . . ?
C5 C2 H2A 108.7 . . ?
C5 C2 H2B 108.7 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 N5 C8 130.9(2) . . ?
C7 N5 N4 109.1(3) . . ?
N4 N5 C8 120.0(3) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
N1 C3 C6 113.0(2) . . ?
N1 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C6 C3 H3A 109.0 . . ?
C6 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N4 N3 N2 114.1(3) . . ?
N2 C7 S1 124.8(2) . . ?
N5 C7 S1 127.8(2) . . ?
N5 C7 N2 107.4(3) . . ?
C13 C8 N5 116.9(3) . . ?
C9 C8 N5 120.1(3) . . ?
C9 C8 C13 122.8(3) . . ?
C8 C13 H13 120.7 . . ?
C8 C13 C12 118.7(3) . . ?
C12 C13 H13 120.7 . . ?
C13 C12 H12 120.7 . . ?
C13 C12 C11 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
N3 N4 N5 105.0(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.8 . . ?
C11 C10 H10 119.1 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?

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
N2 N3 N4 N5 0.5(3) . . . . ?
C1 N1 C2 C5 -57.7(3) . . . . ?
C1 N1 C3 C6 55.5(3) . . . . ?
C2 N1 C1 C4 -60.6(3) . . . . ?
C2 N1 C3 C6 -175.9(2) . . . . ?
N5 C8 C13 C12 -173.8(3) . . . . ?
N5 C8 C9 C10 174.9(3) . . . . ?
C3 N1 C1 C4 65.9(3) . . . . ?
C3 N1 C2 C5 173.5(3) . . . . ?
N3 N2 C7 S1 177.9(2) . . . . ?
N3 N2 C7 N5 1.0(3) . . . . ?
C7 N2 N3 N4 -1.0(4) . . . . ?
C7 N5 C8 C13 -136.3(3) . . . . ?
C7 N5 C8 C9 48.3(4) . . . . ?
C7 N5 N4 N3 0.1(3) . . . . ?
C8 N5 C7 S1 4.9(4) . . . . ?
C8 N5 C7 N2 -178.3(3) . . . . ?
C8 N5 N4 N3 178.0(3) . . . . ?
C8 C13 C12 C11 -1.6(4) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C13 C12 C11 C10 0.4(5) . . . . ?
C12 C11 C10 C9 0.8(5) . . . . ?
N4 N5 C7 S1 -177.5(2) . . . . ?
N4 N5 C7 N2 -0.7(3) . . . . ?
N4 N5 C8 C13 46.4(4) . . . . ?
N4 N5 C8 C9 -129.1(3) . . . . ?
C9 C8 C13 C12 1.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
