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_1567792
_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         'C11 H8 F5 N'
_chemical_formula_sum            'C11 H8 F5 N'
_chemical_formula_weight         249.18
_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   mixed
_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                90
_cell_angle_beta                 93.678(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8320(7)
_cell_length_b                   6.1313(5)
_cell_length_c                   22.4930(17)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      21.9990
_cell_measurement_theta_min      3.6170
_cell_volume                     1077.90(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -60.46 169.54   1.00   15.00   5.96  -1.62 -31.50    --   230
  2  \w    -85.28  18.72   1.00   15.00    --   -1.62 -59.25  20.08  104
  3  \w    -85.28  18.72   1.00   15.00    --   -1.62 -59.25  92.08  104
  4  \w    -85.28  18.72   1.00   15.00    --   -1.62 -59.25-123.92  104
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091482000
_diffrn_orient_matrix_UB_12      0.0942843000
_diffrn_orient_matrix_UB_13      0.0177892000
_diffrn_orient_matrix_UB_21      0.0003667000
_diffrn_orient_matrix_UB_22      0.0664741000
_diffrn_orient_matrix_UB_23      -0.0258017000
_diffrn_orient_matrix_UB_31      -0.0902806000
_diffrn_orient_matrix_UB_32      -0.0093323000
_diffrn_orient_matrix_UB_33      -0.0039466000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9790
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.445
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
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    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0599P)^2^+0.0148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1458
_reflns_number_total             2111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03879j2.cif
_cod_data_source_block           mo_ds3_a
_cod_depositor_comments
'Adding full bibliography for 1567790--1567793.cif.'
_cod_database_code               1567792
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.962
_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.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_shelx_res_checksum              65854
_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 3.984
_oxdiff_exptl_absorpt_empirical_full_min 0.533