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_1569343
_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         'C26 H20 F10 N4 Ni O4'
_chemical_formula_sum            'C26 H20 F10 N4 Ni O4'
_chemical_formula_weight         701.17
_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
_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                88.652(2)
_cell_angle_beta                 84.551(2)
_cell_angle_gamma                71.915(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6514(2)
_cell_length_b                   13.0136(3)
_cell_length_c                   13.6104(4)
_cell_measurement_reflns_used    13124
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.4550
_cell_measurement_theta_min      3.2720
_cell_volume                     1450.03(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 0.996
_diffrn_measured_fraction_theta_max 0.968
_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     16.00 139.00   0.50   12.00    --   49.60  77.00 120.00  246
  2  \w    -40.00 139.00   0.50   12.00    --   49.60   0.00  60.00  358
  3  \w    -40.00  77.00   0.50   12.00    --   49.60 -57.00 -90.00  234
  4  \w    -40.00  77.00   0.50   12.00    --   49.60 -57.00  30.00  234
  5  \w    -40.00  77.00   0.50   12.00    --   49.60 -57.00 150.00  234
  6  \w     83.00 200.00   0.50   80.00    --  110.20  30.00  30.00  234
  7  \w     21.00 144.00   0.50   80.00    --  110.20 -77.00 150.00  246
  8  \w     85.00 200.00   0.50   80.00    --  110.20  45.00  60.00  230
  9  \w     21.00 138.00   0.50   80.00    --  110.20 -30.00  60.00  234
 10  \w     21.00 146.00   0.50   80.00    --  110.20 -82.00  30.00  250
 11  \w     21.00 146.00   0.50   80.00    --  110.20 -82.00 120.00  250
 12  \w     83.00 200.00   0.50   80.00    --  110.20  30.00   0.00  234
 13  \w     21.00 146.00   0.50   80.00    --  110.20 -82.00-120.00  250
 14  \w     21.00 146.00   0.50   80.00    --  110.20 -82.00-180.00  250
 15  \w     21.00 139.00   0.50   80.00    --  110.20 -61.00   0.00  236
 16  \w     85.00 200.00   0.50   80.00    --  110.20  45.00  90.00  230
 17  \w     21.00 146.00   0.50   80.00    --  110.20 -82.00 -90.00  250
 18  \w     21.00 108.50   0.50   80.00    --  110.20 -82.00   0.00  175
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0866529000
_diffrn_orient_matrix_UB_12      0.0098888000
_diffrn_orient_matrix_UB_13      0.0914756000
_diffrn_orient_matrix_UB_21      -0.0989124000
_diffrn_orient_matrix_UB_22      -0.0632654000
_diffrn_orient_matrix_UB_23      0.0611823000
_diffrn_orient_matrix_UB_31      0.1345343000
_diffrn_orient_matrix_UB_32      -0.1068127000
_diffrn_orient_matrix_UB_33      -0.0286023000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.952
_diffrn_reflns_theta_min         3.262
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80377
_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    1.606
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         6117
_refine_ls_number_restraints     512
_refine_ls_restrained_S_all      1.236
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0668P)^2^+1.0414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5485
_reflns_number_total             6117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01861j3.cif
_cod_data_source_block           jk1210
_cod_original_cell_volume        1450.02(7)
_cod_database_code               1569343
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C27H16N4O8F10Ni1
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.847
_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
2. Restrained distances
 F5B-F4B \\sim F4A-F3A \\sim F4A-F5A \\sim F3A-F5A
 with sigma of 0.04
 C23-F5B \\sim C23-F4A \\sim C23-F3B \\sim C23-F3A \\sim C23-F5A \\sim C23-F4B
\\sim C23-C22A \\sim C23-C22B
 with sigma of 0.02
 C22B-F1B \\sim C22B-F2B \\sim C22B-C23
 with sigma of 0.02
 C26-F10A \\sim C26-F8B \\sim C26-F9A \\sim C26-F9B \\sim C26-F8A \\sim
C26-C25B \\sim C26-F10B \\sim C26-
 C25A
 with sigma of 0.02
 C21-C22A \\sim C21-O4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O3 \\sim F6A \\sim F7A \\sim F8A \\sim F9A \\sim F10A \\sim C24 \\sim
C25A \\sim C26: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
F1A \\sim F1B \\sim F2A \\sim F2B \\sim O2 \\sim F3A \\sim F3B \\sim F5A \\sim
F5B \\sim C21 \\sim C22A \\sim C22B \\sim C23: within 2A with sigma of 0.001
and sigma for terminal atoms of 0.004 within 2A
4. Rigid body (RIGU) restrains
 O1, O3, F6A, F6B, F7A, F7B, F8A, F8B, F9A, F9B, F10A, F10B, C24, C25A, C25B,
 C26
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F1A, F1B, F2A, F2B, O2, F3A, F3B, F5A, F5B, C21, C22A, C22B, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(F7B)=Sof(F8B)=
 Sof(F9B)=Sof(F10B)=Sof(C22B)=Sof(C25B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(F7A)=Sof(F8A)=
 Sof(F9A)=Sof(F10A)=Sof(C22A)=Sof(C25A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17), C18(H18)
6.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              38742
_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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.648