Ligand-free nickel catalyzed perfluoroalkylation of arenes and heteroarenes.
Deolka, Shubham; Govindarajan, Ramadoss; Vasylevskyi, Serhii; Roy, Michael C.; Khusnutdinova, Julia R.; Khaskin, Eugene; Chemical science 13 (2022) 12971–12979; doi:10.1039/d2sc03879j

data_1567791
_publ_section_title
;
 Ligand-free nickel catalyzed perfluoroalkylation of arenes and
 heteroarenes.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              12971
_journal_page_last               12979
_journal_paper_doi               10.1039/d2sc03879j
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C9 H9 F5 N2 O3'
_chemical_formula_sum            'C9 H9 F5 N2 O3'
_chemical_formula_weight         288.18
_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             2022-03-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                82.449(6)
_cell_angle_beta                 72.420(7)
_cell_angle_gamma                77.031(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9519(6)
_cell_length_b                   8.3267(6)
_cell_length_c                   9.1611(7)
_cell_measurement_reflns_used    3768
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.9680
_cell_measurement_theta_min      5.0840
_cell_volume                     562.18(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.959
_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     24.00 139.00   0.50    5.00    --   49.60  38.00-120.00  230
  2  \w     22.00 139.00   0.50    5.00    --   49.60  57.00 -90.00  234
  3  \w    -40.00  85.00   0.50    5.00    --   49.60 -82.00  90.00  250
  4  \w    -40.00  75.00   0.50    5.00    --   49.60 -38.00 -30.00  230
  5  \w    -40.00  75.00   0.50    5.00    --   49.60 -38.00  60.00  230
  6  \w     21.00 146.00   0.50   50.00    --  110.20 -82.00  30.00  250
  7  \w     75.00 200.00   0.50   50.00    --  110.20  82.00  60.00  250
  8  \w     75.00 200.00   0.50   50.00    --  110.20  82.00 -30.00  250
  9  \w     21.00 146.00   0.50   50.00    --  110.20 -82.00-180.00  250
 10  \w     65.00 200.00   0.50   50.00    --  110.20  15.00  30.00  270
 11  \w     83.00 200.00   0.50   50.00    --  110.20  30.00 -90.00  234
 12  \w     21.00 139.00   0.50   50.00    --  110.20 -61.00  30.00  236
 13  \w     21.00 146.00   0.50   50.00    --  110.20 -82.00 -30.00  250
 14  \w     77.00 200.00   0.50   50.00    --  110.20  77.00  90.00  246
 15  \w     65.00 200.00   0.50   50.00    --  110.20  15.00   0.00  270
 16  \w     21.00 121.00   0.50   50.00    --  110.20 -82.00 120.00  200
;
_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      0.1190836000
_diffrn_orient_matrix_UB_12      -0.1062615000
_diffrn_orient_matrix_UB_13      0.0958857000
_diffrn_orient_matrix_UB_21      0.1688392000
_diffrn_orient_matrix_UB_22      0.0144277000
_diffrn_orient_matrix_UB_23      -0.1347647000
_diffrn_orient_matrix_UB_31      0.0159576000
_diffrn_orient_matrix_UB_32      0.1572130000
_diffrn_orient_matrix_UB_33      0.0625207000
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7514
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.873
_diffrn_reflns_theta_min         5.076
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59899
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0887P)^2^+0.0766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2051
_reflns_number_total             2353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03879j2.cif
_cod_data_source_block           jk1286
_cod_depositor_comments
'Adding full bibliography for 1567790--1567793.cif.'
_cod_database_code               1567791
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C5H4O3F5N2
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.815
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              62273
_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 0.774