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#$Date: 2025-04-05 05:28:31 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573879.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_1573879
loop_
_publ_author_name
'Luff, Martin S.'
'Filipovic, Tin M.'
'Corsei, Celine S.'
'Oppel, Kai'
'Krummenacher, Ivo'
'Bertermann, Rüdiger'
'Finze, Maik'
'Braunschweig, Holger'
'Radius, Udo'
_publ_section_title
;
 Azolium-2-dithiocarboxylates as redox active ligands in nickel chemistry.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              5142
_journal_page_last               5154
_journal_paper_doi               10.1039/d4sc08449g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C42 H62 N2 Ni S4, C6 H6'
_chemical_formula_sum            'C48 H68 N2 Ni S4'
_chemical_formula_weight         859.99
_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_block_doi                 10.5517/ccdc.csd.cc2lwp28
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-12 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                94.4900(10)
_cell_angle_beta                 97.7310(10)
_cell_angle_gamma                97.2310(10)
_cell_formula_units_Z            1
_cell_length_a                   8.83580(10)
_cell_length_b                   9.0954(2)
_cell_length_c                   14.2686(2)
_cell_measurement_reflns_used    18640
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1710
_cell_measurement_theta_min      3.1820
_cell_volume                     1121.94(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20196
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        72.000
_diffrn_reflns_theta_max         77.339
_diffrn_reflns_theta_min         4.924
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.616
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0299
_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)+(0.0463P)²+0.5566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4462
_reflns_number_total             4581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc08449g2.cif
_cod_data_source_block           Compound_3a
_cod_depositor_comments
'Adding full bibliography for 1573879--1573889.cif.'
_cod_database_code               1573879
_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_min   0.528
_shelx_estimated_absorpt_t_max   0.762
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
Ni01 Ni 0.500000 0.000000 0.000000 0.01241(9) Uani 1 2 d S . P . .
S002 S 0.27297(3) 0.02044(3) 0.03564(2) 0.01510(9) Uani 1 1 d . . . . .
S003 S 0.55081(3) 0.19367(3) 0.10613(2) 0.01396(9) Uani 1 1 d . . . . .
N004 N 0.33308(12) 0.39457(11) 0.21811(7) 0.0116(2) Uani 1 1 d . . . . .
C005 C 0.60466(14) 0.51662(13) 0.24939(9) 0.0129(2) Uani 1 1 d . . . . .
C006 C 0.77706(15) 0.44437(15) 0.37929(9) 0.0166(3) Uani 1 1 d . . . . .
H006 H 0.876346 0.455450 0.416226 0.020 Uiso 1 1 calc R U . . .
C007 C 0.48667(14) 0.41179(13) 0.27126(8) 0.0115(2) Uani 1 1 d . . . . .
C008 C 0.09361(14) 0.25512(14) 0.14772(9) 0.0136(2) Uani 1 1 d . . . . .
C009 C 0.27044(14) 0.27172(13) 0.15831(8) 0.0114(2) Uani 1 1 d . . . . .
C00A C 0.65958(15) 0.34035(14) 0.39901(9) 0.0158(3) Uani 1 1 d . . . . .
H00A H 0.679958 0.279845 0.449319 0.019 Uiso 1 1 calc R U . . .
C00B C 0.06803(15) 0.37552(15) 0.22396(9) 0.0160(3) Uani 1 1 d . . . . .
H00B H -0.022540 0.423804 0.201119 0.019 Uiso 1 1 calc R U . . .
H00C H 0.049386 0.330400 0.283014 0.019 Uiso 1 1 calc R U . . .
C00C C 0.21389(15) 0.49023(14) 0.24291(9) 0.0152(3) Uani 1 1 d . . . . .
C00D C 0.58271(15) 0.61365(14) 0.16805(9) 0.0157(3) Uani 1 1 d . . . . .
H00D H 0.475361 0.585040 0.133741 0.019 Uiso 1 1 calc R U . . .
C00E C 0.20296(16) 0.61746(15) 0.17842(10) 0.0202(3) Uani 1 1 d . . . . .
H00E H 0.198213 0.577843 0.112056 0.030 Uiso 1 1 calc R U . . .
H00F H 0.293927 0.692900 0.196267 0.030 Uiso 1 1 calc R U . . .
H00G H 0.109778 0.662700 0.185855 0.030 Uiso 1 1 calc R U . . .
C00F C 0.02051(15) 0.28376(15) 0.04803(9) 0.0160(3) Uani 1 1 d . . . . .
H00H H 0.063190 0.382852 0.033691 0.024 Uiso 1 1 calc R U . . .
H00I H -0.091397 0.278410 0.045848 0.024 Uiso 1 1 calc R U . . .
H00J H 0.043120 0.208288 0.000974 0.024 Uiso 1 1 calc R U . . .
C00G C 0.74875(15) 0.53189(14) 0.30550(9) 0.0154(2) Uani 1 1 d . . . . .
H00K H 0.829156 0.603885 0.292796 0.019 Uiso 1 1 calc R U . . .
C00H C 0.35379(14) 0.17714(13) 0.11125(8) 0.0123(2) Uani 1 1 d . . . . .
C00I C 0.51253(14) 0.32261(14) 0.34677(9) 0.0129(2) Uani 1 1 d . . . . .
C00J C 0.38896(15) 0.20712(14) 0.37350(9) 0.0151(2) Uani 1 1 d . . . . .
H00L H 0.286983 0.223692 0.339314 0.018 Uiso 1 1 calc R U . . .
C00K C 0.02177(15) 0.10169(15) 0.17166(9) 0.0172(3) Uani 1 1 d . . . . .
H00M H -0.086497 0.104661 0.179079 0.026 Uiso 1 1 calc R U . . .
H00N H 0.078195 0.077004 0.231007 0.026 Uiso 1 1 calc R U . . .
H00O H 0.027953 0.025880 0.120107 0.026 Uiso 1 1 calc R U . . .
C00L C 0.24877(16) 0.55600(16) 0.34639(10) 0.0215(3) Uani 1 1 d . . . . .
H00P H 0.347484 0.621753 0.356627 0.032 Uiso 1 1 calc R U . . .
H00Q H 0.254631 0.475372 0.387884 0.032 Uiso 1 1 calc R U . . .
H00R H 0.166624 0.613154 0.361146 0.032 Uiso 1 1 calc R U . . .
C00M C 0.60064(18) 0.77819(15) 0.20657(11) 0.0238(3) Uani 1 1 d . . . . .
H00S H 0.565871 0.837245 0.155314 0.036 Uiso 1 1 calc R U . . .
H00T H 0.709248 0.813223 0.231136 0.036 Uiso 1 1 calc R U . . .
H00U H 0.538245 0.789163 0.257857 0.036 Uiso 1 1 calc R U . . .
C00N C 0.69494(17) 0.59203(17) 0.09672(10) 0.0225(3) Uani 1 1 d . . . . .
H00V H 0.682879 0.486724 0.072539 0.034 Uiso 1 1 calc R U . . .
H00W H 0.800957 0.623388 0.128244 0.034 Uiso 1 1 calc R U . . .
H00X H 0.672790 0.652142 0.043746 0.034 Uiso 1 1 calc R U . . .
C00O C 0.95756(17) 0.14001(16) 0.51559(10) 0.0223(3) Uani 1 1 d . . . . .
H00Y H 0.928689 0.236381 0.526299 0.027 Uiso 1 1 calc R U . . .
C00P C 0.38067(16) 0.22215(16) 0.48058(9) 0.0204(3) Uani 1 1 d . . . . .
H00Z H 0.369429 0.325069 0.501130 0.031 Uiso 1 1 calc R U . . .
H010 H 0.475445 0.195929 0.515273 0.031 Uiso 1 1 calc R U . . .
H011 H 0.291831 0.155028 0.493681 0.031 Uiso 1 1 calc R U . . .
C00Q C 0.93916(17) 0.07100(16) 0.42377(10) 0.0215(3) Uani 1 1 d . . . . .
H012 H 0.897219 0.119704 0.371785 0.026 Uiso 1 1 calc R U . . .
C00R C 0.98211(16) -0.06909(16) 0.40815(10) 0.0212(3) Uani 1 1 d . . . . .
H013 H 0.970298 -0.116520 0.345365 0.025 Uiso 1 1 calc R U . . .
C00S C 0.41704(18) 0.04924(15) 0.34149(10) 0.0216(3) Uani 1 1 d . . . . .
H014 H 0.417095 0.039316 0.272605 0.032 Uiso 1 1 calc R U . . .
H015 H 0.335030 -0.023182 0.357616 0.032 Uiso 1 1 calc R U . . .
H016 H 0.516945 0.030660 0.373776 0.032 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 0.0181 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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4DT03497J 2025
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
S002 Ni01 S002 180.0 2_655 . ?
S002 Ni01 S003 78.830(11) 2_655 2_655 ?
S002 Ni01 S003 101.171(11) . 2_655 ?
S002 Ni01 S003 101.170(11) 2_655 . ?
S002 Ni01 S003 78.829(11) . . ?
S003 Ni01 S003 180.000(12) 2_655 . ?
C00H S002 Ni01 88.38(4) . . ?
C00H S003 Ni01 87.24(4) . . ?
C009 N004 C007 123.37(10) . . ?
C009 N004 C00C 112.48(10) . . ?
C007 N004 C00C 122.30(10) . . ?
C00G C005 C007 118.10(11) . . ?
C00G C005 C00D 118.62(11) . . ?
C007 C005 C00D 123.27(11) . . ?
C00G C006 C00A 119.61(12) . . ?
C00G C006 H006 120.2 . . ?
C00A C006 H006 120.2 . . ?
C005 C007 C00I 121.43(11) . . ?
C005 C007 N004 120.81(11) . . ?
C00I C007 N004 117.74(11) . . ?
C009 C008 C00F 112.35(10) . . ?
C009 C008 C00B 101.81(10) . . ?
C00F C008 C00B 111.51(10) . . ?
C009 C008 C00K 112.61(10) . . ?
C00F C008 C00K 109.38(10) . . ?
C00B C008 C00K 108.97(10) . . ?
N004 C009 C00H 125.11(11) . . ?
N004 C009 C008 110.09(10) . . ?
C00H C009 C008 124.77(11) . . ?
C006 C00A C00I 121.51(12) . . ?
C006 C00A H00A 119.2 . . ?
C00I C00A H00A 119.2 . . ?
C00C C00B C008 107.37(10) . . ?
C00C C00B H00B 110.2 . . ?
C008 C00B H00B 110.2 . . ?
C00C C00B H00C 110.2 . . ?
C008 C00B H00C 110.2 . . ?
H00B C00B H00C 108.5 . . ?
N004 C00C C00L 111.46(10) . . ?
N004 C00C C00B 100.66(10) . . ?
C00L C00C C00B 112.20(11) . . ?
N004 C00C C00E 111.54(10) . . ?
C00L C00C C00E 109.09(11) . . ?
C00B C00C C00E 111.74(11) . . ?
C005 C00D C00N 112.25(11) . . ?
C005 C00D C00M 110.29(11) . . ?
C00N C00D C00M 109.98(11) . . ?
C005 C00D H00D 108.1 . . ?
C00N C00D H00D 108.1 . . ?
C00M C00D H00D 108.1 . . ?
C00C C00E H00E 109.5 . . ?
C00C C00E H00F 109.5 . . ?
H00E C00E H00F 109.5 . . ?
C00C C00E H00G 109.5 . . ?
H00E C00E H00G 109.5 . . ?
H00F C00E H00G 109.5 . . ?
C008 C00F H00H 109.5 . . ?
C008 C00F H00I 109.5 . . ?
H00H C00F H00I 109.5 . . ?
C008 C00F H00J 109.5 . . ?
H00H C00F H00J 109.5 . . ?
H00I C00F H00J 109.5 . . ?
C006 C00G C005 121.39(12) . . ?
C006 C00G H00K 119.3 . . ?
C005 C00G H00K 119.3 . . ?
C009 C00H S002 124.77(9) . . ?
C009 C00H S003 129.62(10) . . ?
S002 C00H S003 105.44(7) . . ?
C00A C00I C007 117.94(11) . . ?
C00A C00I C00J 118.42(11) . . ?
C007 C00I C00J 123.64(11) . . ?
C00I C00J C00S 110.64(11) . . ?
C00I C00J C00P 112.01(10) . . ?
C00S C00J C00P 110.09(11) . . ?
C00I C00J H00L 108.0 . . ?
C00S C00J H00L 108.0 . . ?
C00P C00J H00L 108.0 . . ?
C008 C00K H00M 109.5 . . ?
C008 C00K H00N 109.5 . . ?
H00M C00K H00N 109.5 . . ?
C008 C00K H00O 109.5 . . ?
H00M C00K H00O 109.5 . . ?
H00N C00K H00O 109.5 . . ?
C00C C00L H00P 109.5 . . ?
C00C C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C00C C00L H00R 109.5 . . ?
H00P C00L H00R 109.5 . . ?
H00Q C00L H00R 109.5 . . ?
C00D C00M H00S 109.5 . . ?
C00D C00M H00T 109.5 . . ?
H00S C00M H00T 109.5 . . ?
C00D C00M H00U 109.5 . . ?
H00S C00M H00U 109.5 . . ?
H00T C00M H00U 109.5 . . ?
C00D C00N H00V 109.5 . . ?
C00D C00N H00W 109.5 . . ?
H00V C00N H00W 109.5 . . ?
C00D C00N H00X 109.5 . . ?
H00V C00N H00X 109.5 . . ?
H00W C00N H00X 109.5 . . ?
C00R C00O C00Q 120.38(13) 2_756 . ?
C00R C00O H00Y 119.8 2_756 . ?
C00Q C00O H00Y 119.8 . . ?
C00J C00P H00Z 109.5 . . ?
C00J C00P H010 109.5 . . ?
H00Z C00P H010 109.5 . . ?
C00J C00P H011 109.5 . . ?
H00Z C00P H011 109.5 . . ?
H010 C00P H011 109.5 . . ?
C00R C00Q C00O 119.78(13) . . ?
C00R C00Q H012 120.1 . . ?
C00O C00Q H012 120.1 . . ?
C00Q C00R C00O 119.84(13) . 2_756 ?
C00Q C00R H013 120.1 . . ?
C00O C00R H013 120.1 2_756 . ?
C00J C00S H014 109.5 . . ?
C00J C00S H015 109.5 . . ?
H014 C00S H015 109.5 . . ?
C00J C00S H016 109.5 . . ?
H014 C00S H016 109.5 . . ?
H015 C00S H016 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
Ni01 S002 2.1612(3) 2_655 ?
Ni01 S002 2.1612(3) . ?
Ni01 S003 2.1904(3) 2_655 ?
Ni01 S003 2.1904(3) . ?
S002 C00H 1.7323(12) . ?
S003 C00H 1.7402(12) . ?
N004 C009 1.3605(16) . ?
N004 C007 1.4465(15) . ?
N004 C00C 1.5080(16) . ?
C005 C00G 1.3945(18) . ?
C005 C007 1.4062(17) . ?
C005 C00D 1.5187(16) . ?
C006 C00G 1.3841(18) . ?
C006 C00A 1.3874(18) . ?
C006 H006 0.9500 . ?
C007 C00I 1.4101(17) . ?
C008 C009 1.5364(17) . ?
C008 C00F 1.5368(17) . ?
C008 C00B 1.5412(17) . ?
C008 C00K 1.5418(17) . ?
C009 C00H 1.3911(17) . ?
C00A C00I 1.3920(18) . ?
C00A H00A 0.9500 . ?
C00B C00C 1.5318(18) . ?
C00B H00B 0.9900 . ?
C00B H00C 0.9900 . ?
C00C C00L 1.5250(17) . ?
C00C C00E 1.5383(18) . ?
C00D C00N 1.5321(18) . ?
C00D C00M 1.5345(18) . ?
C00D H00D 1.0000 . ?
C00E H00E 0.9800 . ?
C00E H00F 0.9800 . ?
C00E H00G 0.9800 . ?
C00F H00H 0.9800 . ?
C00F H00I 0.9800 . ?
C00F H00J 0.9800 . ?
C00G H00K 0.9500 . ?
C00I C00J 1.5255(17) . ?
C00J C00S 1.5328(18) . ?
C00J C00P 1.5358(17) . ?
C00J H00L 1.0000 . ?
C00K H00M 0.9800 . ?
C00K H00N 0.9800 . ?
C00K H00O 0.9800 . ?
C00L H00P 0.9800 . ?
C00L H00Q 0.9800 . ?
C00L H00R 0.9800 . ?
C00M H00S 0.9800 . ?
C00M H00T 0.9800 . ?
C00M H00U 0.9800 . ?
C00N H00V 0.9800 . ?
C00N H00W 0.9800 . ?
C00N H00X 0.9800 . ?
C00O C00R 1.387(2) 2_756 ?
C00O C00Q 1.388(2) . ?
C00O H00Y 0.9500 . ?
C00P H00Z 0.9800 . ?
C00P H010 0.9800 . ?
C00P H011 0.9800 . ?
C00Q C00R 1.385(2) . ?
C00Q H012 0.9500 . ?
C00R H013 0.9500 . ?
C00S H014 0.9800 . ?
C00S H015 0.9800 . ?
C00S H016 0.9800 . ?
