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_7714920
_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         'C39.92 H47.28 Cl0.12 N7 Ni O6.16'
_chemical_formula_sum            'C39.92 H47.28 Cl0.12 N7 Ni O6.16'
_chemical_formula_weight         786.69
_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             2023-11-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2879(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.26757(15)
_cell_length_b                   13.99843(13)
_cell_length_c                   22.5929(2)
_cell_measurement_reflns_used    19755
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      72.8240
_cell_measurement_theta_min      3.1460
_cell_volume                     3848.46(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.91a 64-bit (release 29-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     30.00 106.00   0.50   10.00    --   62.92   9.00  43.00  152
  2  \w     30.00 106.00   0.50   10.00    --   62.92   9.00  43.00  152
  3  \w   -107.00 -30.00   0.50   10.00    --  -63.82  -9.00-130.00  154
  4  \w     43.00 119.00   0.50   10.00    --   75.87   9.00  43.00  152
  5  \w   -119.00 -43.00   0.50   10.00    --  -76.65  -9.00-130.00  152
  6  \w    -90.00 -58.00   0.50   10.00    --  -50.00 -65.00  80.24   64
  7  \w     25.00  71.00   0.50   10.00    --   62.92 -95.00-150.00   92
  8  \w     25.00  71.00   0.50   10.00    --   62.92 -95.00 150.00   92
  9  \w   -106.00 -75.00   0.50   10.00    --  -70.00 -74.00-109.13   62
 10  \w   -113.00 -80.00   0.50   10.00    --  -70.00 -54.00-173.72   66
 11  \w   -100.00 -32.00   0.50   10.00    --  -73.68 125.00  90.00  136
 12  \w   -116.00 -40.00   0.50   10.00    --  -73.68  -9.00-130.00  152
 13  \w   -100.00 -32.00   0.50   10.00    --  -73.68 125.00  90.00  136
 14  \w   -120.00 -87.00   0.50   10.00    --  -74.00 -41.00-151.06   66
 15  \w   -110.00 -79.00   0.50   10.00    --  -74.00 -74.00 -20.75   62
 16  \w     38.00  84.00   0.50   10.00    --   75.87 -95.00-180.00   92
 17  \w   -117.00 -86.00   0.50   10.00    --  -78.25 -67.00 108.08   62
 18  \w   -114.00 -79.00   0.50   10.00    --  -78.25 -90.00-145.15   70
 19  \w   -112.00 -36.00   0.50   10.00    --  -78.25 135.00  79.99  152
 20  \w    -91.00 -39.00   0.50   10.00    --  -78.25 102.00 144.73  104
 21  \w     68.00 127.00   0.50   10.00    --   79.75  24.00-155.94  118
 22  \w     90.00 127.00   0.50   10.00    --   79.75  36.00-121.52   74
 23  \w     38.00 105.00   0.50   10.00    --   79.75-122.00  50.60  134
 24  \w     48.00 124.00   0.50   10.00    --   79.75  13.00  28.95  152
 25  \w     68.00 127.00   0.50   10.00    --   79.75  24.00 162.11  118
 26  \w     37.00 108.00   0.50   10.00    --   79.75-126.00 135.61  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356826000
_diffrn_orient_matrix_UB_12      0.0100496000
_diffrn_orient_matrix_UB_13      0.0675898000
_diffrn_orient_matrix_UB_21      -0.1206777000
_diffrn_orient_matrix_UB_22      -0.0084267000
_diffrn_orient_matrix_UB_23      0.0114022000
_diffrn_orient_matrix_UB_31      0.0127880000
_diffrn_orient_matrix_UB_32      -0.1093464000
_diffrn_orient_matrix_UB_33      0.0054048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47663
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.440
_diffrn_reflns_theta_min         3.723
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       plate
_exptl_crystal_F_000             1660
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         7565
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0638
_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/[\s^2^(Fo^2^)+(0.0560P)^2^+6.9852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6505
_reflns_number_total             7565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt03746k2.cif
_cod_data_source_block           ni_malon4_abs
_cod_depositor_comments
'Adding full bibliography for 7714908--7714920.cif.'
_cod_database_code               7714920
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C102  H0  N66  O62  Cl0  Ni4  '
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.905
_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
 C29-C28A \\sim C29-C28 \\sim C28A-C27 \\sim C28-C27
 with sigma of 0.02
 C19A-C17 \\sim C19-C17 \\sim C20A-C17 \\sim C20-C17 \\sim C18A-C17 \\sim
C18-C17
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C28A \\sim C28: within 1.9A with sigma of 0.02 and sigma for terminal atoms of
0.02 within 1.9A
C20 \\sim C20A \\sim C19 \\sim C19A \\sim C17 \\sim C18A \\sim C18: within 1.9A
with sigma of 0.02 and sigma for terminal atoms of 0.02 within 1.9A
4. Rigid body (RIGU) restrains
 C19, C19A, C17, C20, C20A, C18A, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Ni1(0.88) O1(0.88) O3(0.88) O2(0.88) O5(0.88) O7(0.88) O4(0.88)
 O6(0.88) H27A(0.8) H27B(0.8) H27C(0.2) H27D(0.2) C34(0.88) C39(0.88)
 H39A(0.88) H39B(0.88) C33(0.88) C35(0.88) C38(0.88) H38A(0.88) H38B(0.88)
 H38C(0.88) C40(0.88) C18(0.86) H18A(0.86) H18B(0.86) H18C(0.86) C37(0.88)
 C28(0.8) H28A(0.8) H28B(0.8) H29A(0.8) H29B(0.8) C36(0.88) H36A(0.88)
 H36B(0.88) H36C(0.88) C20(0.86) H20A(0.86) H20B(0.86) H20C(0.86) C19(0.86)
 H19A(0.86) H19B(0.86) H19C(0.86) C41(0.88) H41A(0.88) H41B(0.88) H41C(0.88)
 Ni1A(0.12) Cl1A(0.12) C20A(0.14) H20D(0.14) H20E(0.14) H20F(0.14) C18A(0.14)
 H18D(0.14) H18E(0.14) H18F(0.14) C19A(0.14) H19D(0.14) H19E(0.14) H19F(0.14)
 C28A(0.2) H28C(0.2) H28D(0.2)
6.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27(H27C,H27D), C30(H30A,H30B), C39(H39A,H39B), C21(H21A,
 H21B), C24(H24A,H24B), C22(H22A,H22B), C28(H28A,H28B), C23(H23A,H23B),
 C29(H29A,H29B), C28A(H28C,H28D)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C3(H3), C10(H10)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C38(H38A,H38B,H38C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C36(H36A,H36B,H36C), C20(H20A,H20B,H20C), C19(H19A,
 H19B,H19C), C41(H41A,H41B,H41C), C20A(H20D,H20E,H20F), C18A(H18D,H18E,H18F),
 C19A(H19D,H19E,H19F)
;
_shelx_res_checksum              884
_shelx_hkl_checksum              13435
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, Cryostream 700'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.781