A mesoionic carbene stabilized nickel(II) hydroxide complex: a facile precursor for C-H activation chemistry.
Pavun, Anna; Niess, Raffael; Scheibel, Lucas A.; Seidl, Michael; Hohloch, Stephan; Dalton transactions (Cambridge, England : 2003) 53 (2024) 2749–2761; doi:10.1039/d3dt03746k

data_7714917
_publ_section_title
;
 A mesoionic carbene stabilized nickel(II) hydroxide complex: a facile
 precursor for C-H activation chemistry.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2749
_journal_page_last               2761
_journal_paper_doi               10.1039/d3dt03746k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C33 H38 N8 Ni, 0.471(C7 H8), 0.487(C2 H3 N)'
_chemical_formula_sum            'C37.27 H43.23 N8.49 Ni'
_chemical_formula_weight         668.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.01.27 svn.rdd5efbe3 for OlexSys, GUI svn.r6708)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5534(4)
_cell_length_b                   11.2678(4)
_cell_length_c                   23.8559(10)
_cell_measurement_reflns_used    9490
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      27.509
_cell_measurement_theta_min      2.505
_cell_volume                     3322.6(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest, PhotonIII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            74517
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         2.497
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8885.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1417
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7637
_refine_ls_number_restraints     254
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+2.1050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6760
_reflns_number_total             7637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03746k2.cif
_cod_data_source_block           sh_169n_0m
_cod_depositor_comments
'Adding full bibliography for 7714908--7714920.cif.'
_cod_database_code               7714917
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.766
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N7-C1H
 1.14 with sigma of 0.02
 C1A-C1B
 1.51 with sigma of 0.02
 C1B-C1C = C1B-C1G = C1D-C1E
 1.39 with sigma of 0.02
 C1H-N7
 1.137 with sigma of 0.01
 C1C-C1D = C1E-C1F = C1F-C1G
 1.38 with sigma of 0.02
 C1H-C1I
 1.456 with sigma of 0.01
 C1I-N7
 2.593 with sigma of 0.02
 C1A-C1C = C1A-C1G
 2.52 with sigma of 0.04
 N7-C1I
 2.59 with sigma of 0.04
 C1B-C1D
 2.42 with sigma of 0.04
 C1B-C1F
 2.41 with sigma of 0.04
 C1C-C1E
 2.39 with sigma of 0.04
 C1D-C1F = C1E-C1G
 2.4 with sigma of 0.04
 C25-C27 \\sim C25-C27A
 with sigma of 0.02
 C25-C26 \\sim C25-C26A
 with sigma of 0.02
 C25-C28 \\sim C25-C28A
 with sigma of 0.02
 C6-C8 \\sim C6-C8A
 with sigma of 0.02
 C12-C10 \\sim C12-C10A
 with sigma of 0.02
 C10-C8 \\sim C10A-C8A
 with sigma of 0.02
 C6-C10 \\sim C6-C10A
 with sigma of 0.04
 C1B-C1C \\sim C1C-C1D \\sim C1D-C1E \\sim C1E-C1F \\sim C1F-C1G \\sim C1G-C1B
 with sigma of 0.02
 C1B-C1F \\sim C1B-C1D \\sim C1G-C1E \\sim C1C-C1G \\sim C1D-C1F \\sim C1C-C1E
 with sigma of 0.04
 C12-C8 \\sim C12-C8A
 with sigma of 0.04
 C1A-C1G \\sim C1A-C1C
 with sigma of 0.04
3. Restrained planarity
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N7 \\sim C1H \\sim C1I: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F \\sim C1G: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C1B \\sim C1A \\sim C1C \\sim C1G \\sim N7 \\sim C1H \\sim C1D \\sim C1F \\sim
C1I \\sim C1E: within 1.9A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 1.9A
Uanis(C27A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C26A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C28) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 N7, C1H, C1I
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H6BC)=Sof(H6BD)=Sof(H12C)=Sof(H12D)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(C10A)=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(H12A)=Sof(H12B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=FVAR(1)
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(2)
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(2)
 Sof(N7)=Sof(C1H)=Sof(C1I)=Sof(H1IA)=Sof(H1IB)=Sof(H1IC)=FVAR(3)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(C1C)=Sof(H1C)=Sof(C1D)=
 Sof(H1D)=Sof(C1E)=Sof(H1E)=Sof(C1F)=Sof(H1F)=Sof(C1G)=Sof(H1G)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C6(H6AA,H6AB), C6(H6BC,H6BD), C12(H12A,H12B), C12(H12C,H12D), C9(H9A,H9B),
 C7(H7A,H7B), C5(H5A,H5B), C11(H11A,H11B), C10(H10A,H10B), C8(H8A,H8B),
 C8A(H8AA,H8AB), C10A(H10C,H10D)
7.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C17(H17), C22(H22), C15(H15), C1C(H1C), C1D(H1D), C1E(H1E),
 C1F(H1F), C1G(H1G)
7.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C27(H27A,H27B,
 H27C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C28A(H28D,H28E,H28F),
 C27A(H27D,H27E,H27F), C26A(H26D,H26E,H26F), C1A(H1AA,H1AB,H1AC), C1I(H1IA,H1IB,
 H1IC)
;
_shelx_res_checksum              46114
_shelx_hkl_checksum              50765
_olex2_submission_special_instructions 'No special instructions were received'