#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:46:37 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/84/7718468.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_7718468
loop_
_publ_author_name
'Kharraz, Haia'
'Alemany, Pere'
'Canadell, Enric'
'Roisnel, Thierry'
'Cui, Hengbo'
'Kim, Kee Hoon'
'Fourmigué, Marc'
'Lorcy, Dominique'
_publ_section_title
;
 Gold bis(dithiolene) radical with fused pyrazine and dithiine rings on
 dithiolene ligand turns metallic under pressure.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7240
_journal_page_last               7251
_journal_paper_doi               10.1039/d5dt00380f
_journal_volume                  54
_journal_year                    2025
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H4 N4 Ni S8, C8 H20 N'
_chemical_formula_sum            'C20 H24 N5 Ni S8'
_chemical_formula_weight         649.63
_chemical_melting_point          513
_chemical_name_common            (Et4N)[Ni(pzdtdt)2]
_chemical_name_systematic
(tetraethylammonium)[bis([1,4]dithiino[2,3-b]pyrazine-2,3-bis(thiolate))nickelate]
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2025-02-10 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.994(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.976(2)
_cell_length_b                   8.3085(8)
_cell_length_c                   16.7017(17)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5162
_cell_measurement_theta_min      2.5466
_cell_measurement_wavelength     0.710730
_cell_volume                     2641.1(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0149202
_diffrn_orient_matrix_UB_12      -0.0371525
_diffrn_orient_matrix_UB_13      -0.0445388
_diffrn_orient_matrix_UB_21      0.0013934
_diffrn_orient_matrix_UB_22      -0.1136028
_diffrn_orient_matrix_UB_23      0.0206301
_diffrn_orient_matrix_UB_31      -0.0503581
_diffrn_orient_matrix_UB_32      -0.0141511
_diffrn_orient_matrix_UB_33      -0.0486826
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15252
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.675
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    1.389
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0373P)²+1.9565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                2822
_reflns_number_total             3026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5dt00380f2.cif
_cod_data_source_block           HK317_2
_cod_depositor_comments
'Adding full bibliography for 7718467--7718471.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7718468
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ni1 Ni 0.500000 0.000000 0.500000 0.02684(9) Uani 1 2 d S . P . .
S1 S 0.61039(2) -0.03193(5) 0.59756(3) 0.03304(10) Uani 1 1 d . . . . .
S2 S 0.51464(2) 0.25035(5) 0.48173(3) 0.02978(10) Uani 1 1 d . . . . .
S3 S 0.73554(2) 0.18337(5) 0.68642(3) 0.03614(11) Uani 1 1 d . . . . .
S4 S 0.63234(2) 0.48424(4) 0.57034(3) 0.03238(10) Uani 1 1 d . . . . .
C1 C 0.64439(7) 0.16013(19) 0.60995(10) 0.0293(3) Uani 1 1 d . . . . .
C2 C 0.60214(8) 0.28407(18) 0.56050(10) 0.0281(3) Uani 1 1 d . . . . .
C3 C 0.75628(8) 0.31836(18) 0.62149(11) 0.0300(3) Uani 1 1 d . . . . .
C4 C 0.71262(8) 0.44913(18) 0.57373(10) 0.0293(3) Uani 1 1 d . . . . .
N5 N 0.73011(7) 0.55607(16) 0.52946(10) 0.0348(3) Uani 1 1 d . . . . .
C6 C 0.79094(9) 0.5310(2) 0.53174(13) 0.0385(4) Uani 1 1 d . . . . .
H6 H 0.805662 0.604816 0.501375 0.046 Uiso 1 1 calc R U . . .
C7 C 0.83293(9) 0.4006(2) 0.57705(12) 0.0370(4) Uani 1 1 d . . . . .
H7 H 0.875430 0.386701 0.575974 0.044 Uiso 1 1 calc R U . . .
N8 N 0.81628(7) 0.29295(16) 0.62241(10) 0.0343(3) Uani 1 1 d . . . . .
N21 N 0.500000 0.3653(2) 0.750000 0.0311(4) Uani 1 2 d S T P . .
C23 C 0.500000 0.6718(3) 0.750000 0.0622(9) Uani 1 2 d S T P . .
H23A H 0.504537 0.768669 0.786046 0.075 Uiso 0.5 1 calc R U P A .
H23B H 0.536943 0.671194 0.733429 0.075 Uiso 0.5 1 calc R U P . .
H23C H 0.453871 0.671193 0.693591 0.075 Uiso 0.5 1 calc R U P . .
C22 C 0.5077(2) 0.5142(3) 0.8108(2) 0.0350(7) Uani 0.5 1 d . . P A -1
H22A H 0.554071 0.513246 0.868087 0.042 Uiso 0.5 1 calc R U P A -1
H22B H 0.470619 0.513245 0.828066 0.042 Uiso 0.5 1 calc R U P A -1
C24 C 0.51387(18) 0.2241(4) 0.8180(2) 0.0328(6) Uani 0.5 1 d . . P A -1
H24A H 0.562369 0.233104 0.870823 0.039 Uiso 0.5 1 calc R U P A -1
H24B H 0.481250 0.233418 0.842468 0.039 Uiso 0.5 1 calc R U P A -1
C25 C 0.5048(3) 0.0616(4) 0.7741(2) 0.0405(9) Uani 0.5 1 d . . P A -1
H25A H 0.514134 -0.022419 0.820053 0.049 Uiso 0.5 1 calc R U P A -1
H25B H 0.456501 0.050656 0.722593 0.049 Uiso 0.5 1 calc R U P A -1
H25C H 0.537667 0.050341 0.750964 0.049 Uiso 0.5 1 calc R U P A -1
C26 C 0.42386(18) 0.3561(4) 0.6719(2) 0.0360(7) Uani 0.5 1 d . . P A -1
H26A H 0.413829 0.454404 0.633884 0.043 Uiso 0.5 1 calc R U P A -1
H26B H 0.419843 0.263546 0.632217 0.043 Uiso 0.5 1 calc R U P A -1
C27 C 0.3675(6) 0.3394(12) 0.6966(7) 0.049(2) Uani 0.5 1 d . . P A -1
H27A H 0.321559 0.334935 0.639958 0.059 Uiso 0.5 1 calc R U P A -1
H27B H 0.375002 0.240256 0.732153 0.059 Uiso 0.5 1 calc R U P A -1
H27C H 0.368958 0.432035 0.733828 0.059 Uiso 0.5 1 calc R U P A -1
C28 C 0.54772(18) 0.3670(4) 0.7147(2) 0.0352(7) Uani 0.5 1 d . . P A -1
H28A H 0.535387 0.459225 0.671724 0.042 Uiso 0.5 1 calc R U P A -1
H28B H 0.540233 0.267621 0.678192 0.042 Uiso 0.5 1 calc R U P A -1
C29 C 0.6250(6) 0.3787(12) 0.7859(7) 0.0444(18) Uani 0.5 1 d . . P A -1
H29A H 0.652664 0.378951 0.754641 0.053 Uiso 0.5 1 calc R U P A -1
H29B H 0.633699 0.478435 0.821317 0.053 Uiso 0.5 1 calc R U P A -1
H29C H 0.638559 0.286257 0.827804 0.053 Uiso 0.5 1 calc R U P A -1
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'
Ni Ni 0.3393 1.1124 '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
S2 Ni1 S2 180.0 5_656 . ?
S2 Ni1 S1 88.019(14) 5_656 . ?
S2 Ni1 S1 91.982(14) . . ?
S2 Ni1 S1 91.981(14) 5_656 5_656 ?
S2 Ni1 S1 88.019(14) . 5_656 ?
S1 Ni1 S1 180.00(2) . 5_656 ?
C1 S1 Ni1 103.42(5) . . ?
C2 S2 Ni1 103.75(5) . . ?
C1 S3 C3 99.93(7) . . ?
C4 S4 C2 99.82(7) . . ?
C2 C1 S1 120.30(12) . . ?
C2 C1 S3 122.74(12) . . ?
S1 C1 S3 116.93(9) . . ?
C1 C2 S2 120.26(12) . . ?
C1 C2 S4 123.17(12) . . ?
S2 C2 S4 116.56(8) . . ?
N8 C3 C4 121.47(14) . . ?
N8 C3 S3 116.76(12) . . ?
C4 C3 S3 121.74(12) . . ?
N5 C4 C3 121.85(14) . . ?
N5 C4 S4 115.77(12) . . ?
C3 C4 S4 122.37(12) . . ?
C4 N5 C6 116.32(14) . . ?
N5 C6 C7 121.65(16) . . ?
N5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N8 C7 C6 122.64(15) . . ?
N8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C3 N8 C7 116.03(14) . . ?
C28 N21 C26 111.31(18) . . ?
C28 N21 C24 113.0(2) . . ?
C26 N21 C24 108.50(19) . . ?
C28 N21 C22 113.4(2) . . ?
C26 N21 C22 108.2(2) . . ?
C24 N21 C22 101.88(17) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C23 H23A 179.01(12) . 2_656 ?
H23A C23 H23A 69.5 . 2_656 ?
H23B C23 H23A 71.0 . 2_656 ?
H23C C23 H23A 71.0 . 2_656 ?
C22 C23 H23B 70.04(14) . 2_656 ?
H23A C23 H23B 71.0 . 2_656 ?
H23B C23 H23B 179.4 . 2_656 ?
H23C C23 H23B 70.5 . 2_656 ?
H23A C23 H23B 109.5 2_656 2_656 ?
C22 C23 H23C 70.04(14) . 2_656 ?
H23A C23 H23C 71.0 . 2_656 ?
H23B C23 H23C 70.5 . 2_656 ?
H23C C23 H23C 179.4 . 2_656 ?
H23A C23 H23C 109.5 2_656 2_656 ?
H23B C23 H23C 109.5 2_656 2_656 ?
N21 C22 C23 106.9(2) . . ?
N21 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
N21 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.6 . . ?
N21 C22 H23B 120.9(2) . 2_656 ?
C23 C22 H23B 35.76(8) . 2_656 ?
H22A C22 H23B 123.9 . 2_656 ?
H22B C22 H23B 74.6 . 2_656 ?
N21 C22 H23C 120.9(2) . 2_656 ?
C23 C22 H23C 35.76(8) . 2_656 ?
H22A C22 H23C 74.6 . 2_656 ?
H22B C22 H23C 123.9 . 2_656 ?
H23B C22 H23C 61.0 2_656 2_656 ?
C25 C24 N21 113.1(2) . . ?
C25 C24 H24A 109.0 . . ?
N21 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
N21 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N21 118.4(5) . . ?
C27 C26 H26A 107.7 . . ?
N21 C26 H26A 107.7 . . ?
C27 C26 H26B 107.7 . . ?
N21 C26 H26B 107.7 . . ?
H26A C26 H26B 107.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N21 C28 C29 116.1(4) . . ?
N21 C28 H28A 108.3 . . ?
C29 C28 H28A 108.3 . . ?
N21 C28 H28B 108.3 . . ?
C29 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
Ni1 S2 2.1497(4) 5_656 ?
Ni1 S2 2.1497(4) . ?
Ni1 S1 2.1583(4) . ?
Ni1 S1 2.1584(4) 5_656 ?
S1 C1 1.7300(16) . ?
S2 C2 1.7256(15) . ?
S3 C1 1.7673(15) . ?
S3 C3 1.7707(16) . ?
S4 C4 1.7611(15) . ?
S4 C2 1.7675(16) . ?
C1 C2 1.356(2) . ?
C3 N8 1.328(2) . ?
C3 C4 1.404(2) . ?
C4 N5 1.330(2) . ?
N5 C6 1.335(2) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 N8 1.336(2) . ?
C7 H7 0.9500 . ?
N21 C28 1.438(3) . ?
N21 C26 1.525(3) . ?
N21 C24 1.553(3) . ?
N21 C22 1.555(3) . ?
C23 C22 1.613(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 2_656 ?
C23 H23B 0.9800 2_656 ?
C23 H23C 0.9800 2_656 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C25 1.501(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.494(13) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.512(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
Ni1 S1 C1 C2 -1.85(14) . . . . ?
Ni1 S1 C1 S3 179.85(7) . . . . ?
C3 S3 C1 C2 -39.44(15) . . . . ?
C3 S3 C1 S1 138.81(9) . . . . ?
S1 C1 C2 S2 -2.25(19) . . . . ?
S3 C1 C2 S2 175.94(8) . . . . ?
S1 C1 C2 S4 178.99(8) . . . . ?
S3 C1 C2 S4 -2.8(2) . . . . ?
Ni1 S2 C2 C1 5.09(14) . . . . ?
Ni1 S2 C2 S4 -176.08(7) . . . . ?
C4 S4 C2 C1 42.43(15) . . . . ?
C4 S4 C2 S2 -136.37(9) . . . . ?
C1 S3 C3 N8 -139.98(12) . . . . ?
C1 S3 C3 C4 42.02(14) . . . . ?
N8 C3 C4 N5 -2.0(2) . . . . ?
S3 C3 C4 N5 175.95(12) . . . . ?
N8 C3 C4 S4 179.27(12) . . . . ?
S3 C3 C4 S4 -2.83(19) . . . . ?
C2 S4 C4 N5 142.33(12) . . . . ?
C2 S4 C4 C3 -38.82(14) . . . . ?
C3 C4 N5 C6 1.0(2) . . . . ?
S4 C4 N5 C6 179.83(12) . . . . ?
C4 N5 C6 C7 0.4(2) . . . . ?
N5 C6 C7 N8 -1.0(3) . . . . ?
C4 C3 N8 C7 1.3(2) . . . . ?
S3 C3 N8 C7 -176.67(12) . . . . ?
C6 C7 N8 C3 0.1(2) . . . . ?
C28 N21 C22 C23 54.2(3) . . . . ?
C26 N21 C22 C23 -69.9(3) . . . . ?
C24 N21 C22 C23 175.9(2) . . . . ?
C28 N21 C24 C25 -61.9(3) . . . . ?
C26 N21 C24 C25 62.0(3) . . . . ?
C22 N21 C24 C25 176.1(3) . . . . ?
C28 N21 C26 C27 175.0(5) . . . . ?
C24 N21 C26 C27 50.1(5) . . . . ?
C22 N21 C26 C27 -59.7(5) . . . . ?
C26 N21 C28 C29 179.1(5) . . . . ?
C24 N21 C28 C29 -58.5(5) . . . . ?
C22 N21 C28 C29 56.8(5) . . . . ?
