# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_Zhang_DMcTMe2
_database_code_depnum_ccdc_archive 'CCDC 2095600'
loop_
_audit_author_name
_audit_author_address
'Curtis Moore'
;The Ohio State University
United States of America
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            DMcTMe2
_chemical_name_systematic        
1,2-bis(5-(methylthio)-1,3,4-thiadiazol-2-yl)disulfane
_chemical_formula_moiety         'C6 H6 N4 S6'
_chemical_formula_sum            'C6 H6 N4 S6'
_chemical_formula_weight         326.51
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7096(5)
_cell_length_b                   8.5742(6)
_cell_length_c                   9.4537(6)
_cell_angle_alpha                85.493(2)
_cell_angle_beta                 86.271(2)
_cell_angle_gamma                80.637(2)
_cell_volume                     613.82(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9570
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.504
_cell_measurement_theta_min      3.129
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_T_max  0.2657
_exptl_absorpt_correction_T_min  0.2186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8227.
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    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40620
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.532
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Photon II MoTRIUMPH'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Curved-Graphite, Bruker TRIUMPH'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_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                3480
_reflns_number_total             3732
_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 v8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.086
_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)+(0.0157P)²+0.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.33087(4) 0.98890(3) 0.23914(3) 0.01845(6) Uani 1 1 d . . . . .
S2 S 0.57470(4) 0.89984(3) 0.31283(3) 0.01840(6) Uani 1 1 d . . . . .
S3 S 0.24210(3) 0.78289(3) 0.50980(3) 0.01692(6) Uani 1 1 d . . . . .
S4 S 0.71444(4) 0.70670(3) 0.05723(3) 0.02622(7) Uani 1 1 d . . . . .
S5 S -0.04732(4) 0.62985(3) 0.66576(3) 0.01801(6) Uani 1 1 d . . . . .
S6 S 0.79940(4) 0.37669(4) -0.04588(3) 0.02582(7) Uani 1 1 d . . . . .
N1 N 0.03074(13) 0.88336(11) 0.31059(10) 0.01916(18) Uani 1 1 d . . . . .
N2 N -0.06613(12) 0.80236(11) 0.41233(10) 0.01864(18) Uani 1 1 d . . . . .
N3 N 0.59973(13) 0.58527(11) 0.29361(10) 0.01919(18) Uani 1 1 d . . . . .
N4 N 0.65272(13) 0.45961(11) 0.21019(10) 0.01875(18) Uani 1 1 d . . . . .
C1 C 0.18953(14) 0.88363(12) 0.34832(11) 0.01571(18) Uani 1 1 d . . . . .
C2 C 0.02691(13) 0.74395(12) 0.52088(11) 0.01536(18) Uani 1 1 d . . . . .
C3 C 0.62365(14) 0.72005(13) 0.22902(11) 0.01720(19) Uani 1 1 d . . . . .
C4 C 0.71492(14) 0.50488(13) 0.08405(12) 0.0183(2) Uani 1 1 d . . . . .
C5 C -0.26750(15) 0.62362(15) 0.61595(13) 0.0219(2) Uani 1 1 d . . . . .
H5A H -0.262586 0.578124 0.523592 0.033 Uiso 1 1 calc R U . . .
H5B H -0.334025 0.731309 0.609435 0.033 Uiso 1 1 calc R U . . .
H5C H -0.325715 0.558052 0.687720 0.033 Uiso 1 1 calc R U . . .
C6 C 0.81370(19) 0.18997(14) 0.05653(13) 0.0270(2) Uani 1 1 d . . . . .
H6A H 0.866341 0.104575 -0.003401 0.040 Uiso 1 1 calc R U . . .
H6B H 0.695480 0.172554 0.091659 0.040 Uiso 1 1 calc R U . . .
H6C H 0.887079 0.190886 0.137212 0.040 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 S2 2.0547(4) . ?
S1 C1 1.7592(11) . ?
S2 C3 1.7636(11) . ?
S3 C1 1.7321(11) . ?
S3 C2 1.7398(11) . ?
S4 C3 1.7309(11) . ?
S4 C4 1.7286(11) . ?
S5 C2 1.7407(11) . ?
S5 C5 1.8010(12) . ?
S6 C4 1.7367(12) . ?
S6 C6 1.7960(13) . ?
N1 N2 1.3912(13) . ?
N1 C1 1.2976(14) . ?
N2 C2 1.3102(14) . ?
N3 N4 1.3777(13) . ?
N3 C3 1.2985(14) . ?
N4 C4 1.3100(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C1 S1 S2 103.04(4) . . ?
C3 S2 S1 101.13(4) . . ?
C1 S3 C2 85.77(5) . . ?
C4 S4 C3 86.58(5) . . ?
C2 S5 C5 100.12(5) . . ?
C4 S6 C6 100.27(6) . . ?
C1 N1 N2 111.84(9) . . ?
C2 N2 N1 111.91(9) . . ?
C3 N3 N4 112.66(9) . . ?
C4 N4 N3 112.15(9) . . ?
S3 C1 S1 125.01(6) . . ?
N1 C1 S1 119.28(8) . . ?
N1 C1 S3 115.67(8) . . ?
S3 C2 S5 120.10(6) . . ?
N2 C2 S3 114.79(8) . . ?
N2 C2 S5 125.07(8) . . ?
S4 C3 S2 123.23(6) . . ?
N3 C3 S2 122.36(8) . . ?
N3 C3 S4 114.37(8) . . ?
S4 C4 S6 121.41(6) . . ?
N4 C4 S4 114.23(8) . . ?
N4 C4 S6 124.32(9) . . ?
S5 C5 H5A 109.5 . . ?
S5 C5 H5B 109.5 . . ?
S5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
S6 C6 H6A 109.5 . . ?
S6 C6 H6B 109.5 . . ?
S6 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
S1 S2 C3 S4 84.06(7) . . . . ?
S1 S2 C3 N3 -98.35(9) . . . . ?
S2 S1 C1 S3 18.26(7) . . . . ?
S2 S1 C1 N1 -164.23(8) . . . . ?
N1 N2 C2 S3 0.24(12) . . . . ?
N1 N2 C2 S5 -177.71(8) . . . . ?
N2 N1 C1 S1 -176.60(7) . . . . ?
N2 N1 C1 S3 1.14(12) . . . . ?
N3 N4 C4 S4 0.25(12) . . . . ?
N3 N4 C4 S6 177.96(8) . . . . ?
N4 N3 C3 S2 -177.72(8) . . . . ?
N4 N3 C3 S4 0.06(12) . . . . ?
C1 S3 C2 S5 178.36(7) . . . . ?
C1 S3 C2 N2 0.30(8) . . . . ?
C1 N1 N2 C2 -0.87(13) . . . . ?
C2 S3 C1 S1 176.76(8) . . . . ?
C2 S3 C1 N1 -0.83(9) . . . . ?
C3 S4 C4 S6 -177.96(8) . . . . ?
C3 S4 C4 N4 -0.18(9) . . . . ?
C3 N3 N4 C4 -0.20(14) . . . . ?
C4 S4 C3 S2 177.82(8) . . . . ?
C4 S4 C3 N3 0.06(9) . . . . ?
C5 S5 C2 S3 -177.69(7) . . . . ?
C5 S5 C2 N2 0.16(11) . . . . ?
C6 S6 C4 S4 166.44(8) . . . . ?
C6 S6 C4 N4 -11.11(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
