Oxygen transfer reactivity mediated by nickel perfluoroalkyl complexes using molecular oxygen as a terminal oxidant
Deolka, Shubham; Govindarajan, R.; Khaskin, Eugene; Vasylevskyi, Serhii; Bahri, Janet; Fayzullin, Robert R.; Roy, Michael C.; Khusnutdinova, Julia R.; Chemical Science 14 (2023) 7026–7035; doi:10.1039/D3SC01861J

data_1569340
_publ_section_title
;
 Oxygen transfer reactivity mediated by nickel perfluoroalkyl complexes
 using molecular oxygen as a terminal oxidant
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              7026
_journal_page_last               7035
_journal_paper_doi               10.1039/D3SC01861J
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H20 F6 N4 Ni O6, C6 H6'
_chemical_formula_sum            'C28 H26 F6 N4 Ni O6'
_chemical_formula_weight         687.24
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-02-14 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                99.771(4)
_cell_angle_beta                 105.008(4)
_cell_angle_gamma                105.431(4)
_cell_formula_units_Z            1
_cell_length_a                   7.4720(4)
_cell_length_b                   8.6669(4)
_cell_length_c                   12.3403(6)
_cell_measurement_reflns_used    7970
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.8930
_cell_measurement_theta_min      3.8240
_cell_volume                     719.21(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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    -40.00  75.00   0.50   20.30    --   49.60 -38.00 -30.00  230
  2  \w     14.00 139.00   0.50   20.30    --   49.60  82.00  90.00  250
  3  \w    -40.00  85.00   0.50   20.30    --   49.60 -82.00  90.00  250
  4  \w    -40.00  75.00   0.50   20.30    --   49.60 -38.00-180.00  230
  5  \w    -40.00  85.00   0.50   20.30    --   49.60 -82.00 -60.00  250
  6  \w     65.00 200.00   0.50   20.30    --  110.20  15.00  90.00  270
  7  \w     77.00 200.00   0.50   20.30    --  110.20  77.00-120.00  246
  8  \w     21.00 139.00   0.50   20.30    --  110.20 -61.00 150.00  236
  9  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00 -60.00  250
 10  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00-180.00  250
 11  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00  30.00  250
 12  \w     21.00 138.00   0.50   20.30    --  110.20 -30.00 -60.00  234
 13  \w     83.00 200.00   0.50   20.30    --  110.20  30.00   0.00  234
 14  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00 150.00  250
 15  \w     65.00 200.00   0.50   20.30    --  110.20  15.00-180.00  270
 16  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00 -30.00  250
 17  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00-120.00  250
 18  \w     21.00 146.00   0.50   20.30    --  110.20 -82.00  60.00  250
 19  \w     22.00 139.00   0.50   20.30    --   49.60  57.00  30.00  234
 20  \w     14.00 139.00   0.50   20.30    --   49.60  82.00 -90.00  250
 21  \w     22.00 139.00   0.50   20.30    --   49.60  57.00 -60.00  234
 22  \w     16.00 139.00   0.50   20.30    --   49.60  77.00  60.00  246
 23  \w     24.00 139.00   0.50   20.30    --   49.60  38.00-150.00  230
 24  \w     16.00 139.00   0.50   20.30    --   49.60  77.00-180.00  246
 25  \w     83.00 145.00   0.50   20.30    --  110.20  30.00 -30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1377799000
_diffrn_orient_matrix_UB_12      -0.0878489000
_diffrn_orient_matrix_UB_13      0.0580734000
_diffrn_orient_matrix_UB_21      0.1454151000
_diffrn_orient_matrix_UB_22      0.1686310000
_diffrn_orient_matrix_UB_23      0.0774731000
_diffrn_orient_matrix_UB_31      -0.1041311000
_diffrn_orient_matrix_UB_32      -0.0154591000
_diffrn_orient_matrix_UB_33      0.0922209000
_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  0.0703
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14220
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.360
_diffrn_reflns_theta_min         3.837
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0482
_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/[\s^2^(Fo^2^)+(0.0841P)^2^+0.1653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2610
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01861j3.cif
_cod_data_source_block           jk1166
_cod_original_cell_volume        719.22(7)
_cod_database_code               1569340
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C10H8Ni1N4F6O2
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.683
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.85 with sigma of 0.02
 H1A-H1B
 1.34 with sigma of 0.04
 Ni1-H1A \\sim Ni1-H1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1A \\sim C1A \\sim N2A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim
C7A \\sim C8A \\sim C9A: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
N1B \\sim C1B \\sim N2B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim
C7B \\sim C8B \\sim C9B: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
F1A \\sim F1B \\sim F2A \\sim F2B \\sim F3A \\sim F3B: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(F1B)=Sof(N1B)=Sof(C1B)=Sof(H1BA)=Sof(F2B)=Sof(N2B)=Sof(C2B)=Sof(H2B)=
 Sof(F3B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=
 Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=1-FVAR(1)
 Sof(F1A)=Sof(N1A)=Sof(C1A)=Sof(H1AA)=Sof(F2A)=Sof(N2A)=Sof(C2A)=Sof(H2A)=
 Sof(F3A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=
 Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1A(H1AA), C1B(H1BA), C2A(H2A), C2B(H2B), C3A(H3A), C3B(H3B), C6A(H6A),
 C6B(H6B), C7A(H7A), C7B(H7B), C12(H12), C13(H13), C14(H14)
5.b Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC)
;
_shelx_res_checksum              99915
_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 5.418
_oxdiff_exptl_absorpt_empirical_full_min 0.363