#------------------------------------------------------------------------------
#$Date: 2021-11-11 01:14:42 +0200 (Thu, 11 Nov 2021) $
#$Revision: 270582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1565179
loop_
_publ_author_name
'Tuttle, Madison R.'
'Walter, Christopher'
'Brackman, Emma'
'Moore, Curtis'
'Espe, Matthew'
'Rasik, Chris'
'Adams, Paul'
'Zhang, Shiyu'
_publ_section_title
;
 Redox-Active Zinc Thiolates for Low-Cost Rechargeable Aqueous Zn-ion
 Batteries
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04231A
_journal_year                    2021
_chemical_formula_moiety         'C6 H6 N4 S6'
_chemical_formula_sum            'C6 H6 N4 S6'
_chemical_formula_weight         326.51
_chemical_name_common            DMcTMe2
_chemical_name_systematic
1,2-bis(5-(methylthio)-1,3,4-thiadiazol-2-yl)disulfane
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-09 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                85.493(2)
_cell_angle_beta                 86.271(2)
_cell_angle_gamma                80.637(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7096(5)
_cell_length_b                   8.5742(6)
_cell_length_c                   9.4537(6)
_cell_measurement_reflns_used    9570
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.504
_cell_measurement_theta_min      3.129
_cell_volume                     613.82(7)
_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)'
_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_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_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
_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_crystal_colour            Yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       Rod
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.051
_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_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0196
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3480
_reflns_number_total             3732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04231a2.cif
_cod_data_source_block           Zhang_DMcTMe2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_primary' value 'Yellow' was changed
to 'yellow' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1565179
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.708
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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_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_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) . . . . ?
