#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:27:06 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/26/4342646.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_4342646
loop_
_publ_author_name
'Olechnowicz, Frank'
'Hillhouse, Gregory L.'
'Jordan, Richard F.'
_publ_section_title
;
 Synthesis and Reactivity of NHC-Supported
 Ni2(μ(2)-η(2),η(2)-S2)-Bridging Disulfide and Ni2(μ-S)2-Bridging
 Sulfide Complexes.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2705
_journal_page_last               2712
_journal_paper_doi               10.1021/ic502892r
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C54 H74 N4 Ni2 S2'
_chemical_formula_sum            'C54 H74 N4 Ni2 S2'
_chemical_formula_weight         960.70
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 118.0870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8714(9)
_cell_length_b                   12.3451(5)
_cell_length_c                   19.5255(13)
_cell_measurement_reflns_used    9695
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5423
_cell_measurement_theta_min      2.4763
_cell_volume                     5076.4(4)
_computing_cell_refinement       'APEX2 v2013.10-0 (Bruker AXS)'
_computing_data_collection       ShelXtl
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Mercury v3.3.1 (CCDC, 2014)'
_computing_publication_material  enCIFer
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.242
_diffrn_source                   'Incoatec I\mS micro-focus tube'
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.81989
_exptl_absorpt_correction_T_min  0.77226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2013/10 (Bruker AXS Inc.)'
_exptl_crystal_colour            'fluorescent light green'
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.251
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0273
_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)+(0.0350P)²+5.6292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5488
_reflns_number_total             5859
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic502892r_si_002.cif
_cod_data_source_block           FDO05
_cod_depositor_comments
'Adding full bibliography for 4342642--4342646.cif.'
_cod_database_code               4342646
#BEGIN Tags that were not found in dictionaries:
_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   0.794
_shelx_estimated_absorpt_t_max   0.813
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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 0.05073(2) 0.72373(2) 0.25354(2) 0.01474(6) Uani 1 1 d . . . . .
S1 S -0.03703(2) 0.72207(3) 0.14243(2) 0.02580(9) Uani 1 1 d . . . . .
H1A H -0.0403(19) 0.628(3) 0.124(2) 0.045(11) Uiso 0.5 1 d . . P A 1
H1B H -0.043(2) 0.823(4) 0.125(3) 0.067(15) Uiso 0.5 1 d . . P B 2
N1 N 0.16789(5) 0.67418(8) 0.24388(6) 0.01275(19) Uani 1 1 d . . . . .
N2 N 0.16959(5) 0.83077(8) 0.29248(6) 0.01301(19) Uani 1 1 d . . . . .
C1 C 0.13158(6) 0.74147(10) 0.26241(7) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.22651(6) 0.72034(10) 0.26202(7) 0.0144(2) Uani 1 1 d . . . . .
H19 H 0.2594 0.6885 0.2545 0.017 Uiso 1 1 calc R U . . .
C3 C 0.22757(5) 0.81884(10) 0.29231(7) 0.0148(2) Uani 1 1 d . . . . .
H18 H 0.2612 0.8701 0.3100 0.018 Uiso 1 1 calc R U . . .
C4 C 0.14884(6) 0.92992(10) 0.31283(7) 0.0145(2) Uani 1 1 d . . . . .
C5 C 0.10797(6) 0.99887(10) 0.25254(7) 0.0172(2) Uani 1 1 d . . . . .
C6 C 0.09075(6) 1.09629(11) 0.27351(8) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.0634 1.1447 0.2341 0.026 Uiso 1 1 calc R U . . .
C7 C 0.11280(7) 1.12390(11) 0.35069(9) 0.0242(3) Uani 1 1 d . . . . .
H9 H 0.1012 1.1914 0.3638 0.029 Uiso 1 1 calc R U . . .
C8 C 0.15160(7) 1.05343(11) 0.40857(8) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.1661 1.0729 0.4613 0.026 Uiso 1 1 calc R U . . .
C9 C 0.16990(6) 0.95425(10) 0.39109(7) 0.0168(2) Uani 1 1 d . . . . .
C10 C 0.21181(6) 0.87772(10) 0.45575(7) 0.0174(2) Uani 1 1 d . . . . .
H50 H 0.2076 0.8038 0.4329 0.021 Uiso 1 1 calc R U . . .
C11 C 0.28153(6) 0.91209(12) 0.49014(8) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.2947 0.9095 0.4497 0.034 Uiso 1 1 calc R U . . .
H3 H 0.3080 0.8627 0.5323 0.034 Uiso 1 1 calc R U . . .
H2 H 0.2864 0.9860 0.5104 0.034 Uiso 1 1 calc R U . . .
C12 C 0.19159(7) 0.87094(11) 0.51939(8) 0.0223(3) Uani 1 1 d . . . . .
H6 H 0.2164 0.8147 0.5569 0.033 Uiso 1 1 calc R U . . .
H7 H 0.1463 0.8529 0.4960 0.033 Uiso 1 1 calc R U . . .
H5 H 0.1991 0.9409 0.5460 0.033 Uiso 1 1 calc R U . . .
C13 C 0.08408(6) 0.97062(11) 0.16754(7) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.0859 0.8900 0.1637 0.024 Uiso 1 1 calc R U . . .
C14 C 0.12733(8) 1.01939(15) 0.13783(9) 0.0354(4) Uani 1 1 d . . . . .
H13 H 0.1710 0.9949 0.1706 0.053 Uiso 1 1 calc R U . . .
H12 H 0.1256 1.0986 0.1396 0.053 Uiso 1 1 calc R U . . .
H14 H 0.1131 0.9960 0.0842 0.053 Uiso 1 1 calc R U . . .
C15 C 0.01542(7) 1.00531(15) 0.11683(9) 0.0342(3) Uani 1 1 d . . . . .
H15 H 0.0132 1.0845 0.1127 0.051 Uiso 1 1 calc R U . . .
H16 H -0.0107 0.9801 0.1402 0.051 Uiso 1 1 calc R U . . .
H17 H -0.0004 0.9737 0.0650 0.051 Uiso 1 1 calc R U . . .
C16 C 0.14257(5) 0.58016(10) 0.19455(7) 0.0142(2) Uani 1 1 d . . . . .
C17 C 0.12399(6) 0.59306(10) 0.11518(7) 0.0163(2) Uani 1 1 d . . . . .
C18 C 0.10028(6) 0.50255(11) 0.06746(8) 0.0211(3) Uani 1 1 d . . . . .
H29 H 0.0875 0.5091 0.0136 0.025 Uiso 1 1 calc R U . . .
C19 C 0.09500(6) 0.40327(11) 0.09691(8) 0.0229(3) Uani 1 1 d . . . . .
H28 H 0.0793 0.3422 0.0636 0.027 Uiso 1 1 calc R U . . .
C20 C 0.11267(6) 0.39327(11) 0.17521(8) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.1084 0.3251 0.1949 0.025 Uiso 1 1 calc R U . . .
C21 C 0.13663(6) 0.48170(10) 0.22572(7) 0.0164(2) Uani 1 1 d . . . . .
C22 C 0.15280(6) 0.46840(10) 0.31032(7) 0.0180(2) Uani 1 1 d . . . . .
H21 H 0.1711 0.5382 0.3377 0.022 Uiso 1 1 calc R U . . .
C23 C 0.20225(6) 0.37916(11) 0.34982(8) 0.0218(3) Uani 1 1 d . . . . .
H24 H 0.2409 0.3967 0.3464 0.033 Uiso 1 1 calc R U . . .
H23 H 0.1852 0.3099 0.3239 0.033 Uiso 1 1 calc R U . . .
H22 H 0.2124 0.3738 0.4045 0.033 Uiso 1 1 calc R U . . .
C24 C 0.09216(7) 0.44484(12) 0.31625(8) 0.0243(3) Uani 1 1 d . . . . .
H27 H 0.0737 0.3762 0.2902 0.036 Uiso 1 1 calc R U . . .
H26 H 0.0615 0.5035 0.2914 0.036 Uiso 1 1 calc R U . . .
H25 H 0.1025 0.4398 0.3710 0.036 Uiso 1 1 calc R U . . .
C25 C 0.12849(6) 0.70079(11) 0.08037(7) 0.0189(2) Uani 1 1 d . . . . .
H30 H 0.1460 0.7556 0.1231 0.023 Uiso 1 1 calc R U . . .
C26 C 0.06296(7) 0.73980(14) 0.01926(9) 0.0304(3) Uani 1 1 d . . . . .
H32 H 0.0670 0.8111 0.0000 0.046 Uiso 1 1 calc R U . . .
H31 H 0.0346 0.7450 0.0426 0.046 Uiso 1 1 calc R U . . .
H33 H 0.0453 0.6882 -0.0240 0.046 Uiso 1 1 calc R U . . .
C27 C 0.17398(7) 0.69247(12) 0.04564(8) 0.0240(3) Uani 1 1 d . . . . .
H35 H 0.2156 0.6676 0.0856 0.036 Uiso 1 1 calc R U . . .
H34 H 0.1784 0.7637 0.0266 0.036 Uiso 1 1 calc R U . . .
H36 H 0.1570 0.6408 0.0025 0.036 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'
Ni Ni 0.3393 1.1124 '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
C1 Ni1 S1 123.82(4) . .
C1 Ni1 S1 120.72(4) . 2
S1 Ni1 S1 115.096(12) . 2
C1 Ni1 Ni1 173.04(4) . 2
S1 Ni1 Ni1 57.753(11) . 2
S1 Ni1 Ni1 57.354(11) 2 2
Ni1 S1 Ni1 64.891(12) . 2
Ni1 S1 H1A 101.7(19) . .
Ni1 S1 H1A 105.6(19) 2 .
Ni1 S1 H1B 101(2) . .
Ni1 S1 H1B 101(2) 2 .
C1 N1 C2 111.74(10) . .
C1 N1 C16 123.08(10) . .
C2 N1 C16 123.52(10) . .
C1 N2 C3 111.82(10) . .
C1 N2 C4 123.72(10) . .
C3 N2 C4 124.05(10) . .
N1 C1 N2 103.16(10) . .
N1 C1 Ni1 131.36(9) . .
N2 C1 Ni1 125.47(9) . .
C3 C2 N1 106.85(10) . .
C3 C2 H19 126.6 . .
N1 C2 H19 126.6 . .
C2 C3 N2 106.44(10) . .
C2 C3 H18 126.8 . .
N2 C3 H18 126.8 . .
C9 C4 C5 122.36(11) . .
C9 C4 N2 119.29(11) . .
C5 C4 N2 118.35(11) . .
C6 C5 C4 117.42(12) . .
C6 C5 C13 120.53(11) . .
C4 C5 C13 122.04(11) . .
C7 C6 C5 121.25(12) . .
C7 C6 H10 119.4 . .
C5 C6 H10 119.4 . .
C8 C7 C6 120.03(12) . .
C8 C7 H9 120.0 . .
C6 C7 H9 120.0 . .
C7 C8 C9 121.29(12) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C8 C9 C4 117.58(12) . .
C8 C9 C10 120.21(11) . .
C4 C9 C10 122.21(11) . .
C9 C10 C11 110.31(10) . .
C9 C10 C12 111.90(11) . .
C11 C10 C12 110.57(11) . .
C9 C10 H50 108.0 . .
C11 C10 H50 108.0 . .
C12 C10 H50 108.0 . .
C10 C11 H4 109.5 . .
C10 C11 H3 109.5 . .
H4 C11 H3 109.5 . .
C10 C11 H2 109.5 . .
H4 C11 H2 109.5 . .
H3 C11 H2 109.5 . .
C10 C12 H6 109.5 . .
C10 C12 H7 109.5 . .
H6 C12 H7 109.5 . .
C10 C12 H5 109.5 . .
H6 C12 H5 109.5 . .
H7 C12 H5 109.5 . .
C5 C13 C15 112.38(11) . .
C5 C13 C14 110.58(11) . .
C15 C13 C14 110.82(12) . .
C5 C13 H11 107.6 . .
C15 C13 H11 107.6 . .
C14 C13 H11 107.6 . .
C13 C14 H13 109.5 . .
C13 C14 H12 109.5 . .
H13 C14 H12 109.5 . .
C13 C14 H14 109.5 . .
H13 C14 H14 109.5 . .
H12 C14 H14 109.5 . .
C13 C15 H15 109.5 . .
C13 C15 H16 109.5 . .
H15 C15 H16 109.5 . .
C13 C15 H17 109.5 . .
H15 C15 H17 109.5 . .
H16 C15 H17 109.5 . .
C21 C16 C17 122.35(11) . .
C21 C16 N1 120.31(10) . .
C17 C16 N1 117.34(11) . .
C18 C17 C16 117.67(12) . .
C18 C17 C25 119.65(11) . .
C16 C17 C25 122.68(11) . .
C19 C18 C17 121.33(12) . .
C19 C18 H29 119.3 . .
C17 C18 H29 119.3 . .
C18 C19 C20 119.79(12) . .
C18 C19 H28 120.1 . .
C20 C19 H28 120.1 . .
C19 C20 C21 121.23(12) . .
C19 C20 H20 119.4 . .
C21 C20 H20 119.4 . .
C16 C21 C20 117.60(11) . .
C16 C21 C22 122.86(11) . .
C20 C21 C22 119.51(11) . .
C21 C22 C23 111.52(11) . .
C21 C22 C24 109.71(11) . .
C23 C22 C24 110.90(11) . .
C21 C22 H21 108.2 . .
C23 C22 H21 108.2 . .
C24 C22 H21 108.2 . .
C22 C23 H24 109.5 . .
C22 C23 H23 109.5 . .
H24 C23 H23 109.5 . .
C22 C23 H22 109.5 . .
H24 C23 H22 109.5 . .
H23 C23 H22 109.5 . .
C22 C24 H27 109.5 . .
C22 C24 H26 109.5 . .
H27 C24 H26 109.5 . .
C22 C24 H25 109.5 . .
H27 C24 H25 109.5 . .
H26 C24 H25 109.5 . .
C17 C25 C27 110.71(11) . .
C17 C25 C26 111.23(11) . .
C27 C25 C26 110.70(11) . .
C17 C25 H30 108.0 . .
C27 C25 H30 108.0 . .
C26 C25 H30 108.0 . .
C25 C26 H32 109.5 . .
C25 C26 H31 109.5 . .
H32 C26 H31 109.5 . .
C25 C26 H33 109.5 . .
H32 C26 H33 109.5 . .
H31 C26 H33 109.5 . .
C25 C27 H35 109.5 . .
C25 C27 H34 109.5 . .
H35 C27 H34 109.5 . .
C25 C27 H36 109.5 . .
H35 C27 H36 109.5 . .
H34 C27 H36 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.8677(12) .
Ni1 S1 2.1945(4) .
Ni1 S1 2.2042(4) 2
Ni1 Ni1 2.3600(3) 2
S1 Ni1 2.2042(4) 2
S1 H1A 1.21(4) .
S1 H1B 1.28(5) .
N1 C1 1.3666(15) .
N1 C2 1.3934(15) .
N1 C16 1.4464(15) .
N2 C1 1.3718(16) .
N2 C3 1.3934(15) .
N2 C4 1.4446(15) .
C2 C3 1.3472(17) .
C2 H19 0.9500 .
C3 H18 0.9500 .
C4 C9 1.3982(17) .
C4 C5 1.4073(17) .
C5 C6 1.3934(18) .
C5 C13 1.5199(17) .
C6 C7 1.385(2) .
C6 H10 0.9500 .
C7 C8 1.381(2) .
C7 H9 0.9500 .
C8 C9 1.3952(18) .
C8 H8 0.9500 .
C9 C10 1.5159(17) .
C10 C11 1.5326(18) .
C10 C12 1.5327(18) .
C10 H50 1.0000 .
C11 H4 0.9800 .
C11 H3 0.9800 .
C11 H2 0.9800 .
C12 H6 0.9800 .
C12 H7 0.9800 .
C12 H5 0.9800 .
C13 C15 1.5239(19) .
C13 C14 1.5260(19) .
C13 H11 1.0000 .
C14 H13 0.9800 .
C14 H12 0.9800 .
C14 H14 0.9800 .
C15 H15 0.9800 .
C15 H16 0.9800 .
C15 H17 0.9800 .
C16 C21 1.3963(17) .
C16 C17 1.4059(16) .
C17 C18 1.3930(18) .
C17 C25 1.5201(18) .
C18 C19 1.385(2) .
C18 H29 0.9500 .
C19 C20 1.3868(19) .
C19 H28 0.9500 .
C20 C21 1.4002(18) .
C20 H20 0.9500 .
C21 C22 1.5178(17) .
C22 C23 1.5312(18) .
C22 C24 1.5336(18) .
C22 H21 1.0000 .
C23 H24 0.9800 .
C23 H23 0.9800 .
C23 H22 0.9800 .
C24 H27 0.9800 .
C24 H26 0.9800 .
C24 H25 0.9800 .
C25 C27 1.5306(19) .
C25 C26 1.5315(19) .
C25 H30 1.0000 .
C26 H32 0.9800 .
C26 H31 0.9800 .
C26 H33 0.9800 .
C27 H35 0.9800 .
C27 H34 0.9800 .
C27 H36 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139142866
