Electrochemically driven, cobalt–carbon bond-mediated direct intramolecular cyclic and acyclic perfluoroalkylation of (hetero)arenes using X(CF2)4X
Cui, Luxia; Ono, Toshikazu; Hossain, Md. Jakir; Hisaeda, Yoshio; RSC Advances 10 (2020) 24862–24866; doi:10.1039/D0RA05295G

data_7240810
_publ_section_title
;
 Electrochemically driven, cobalt--carbon bond-mediated direct
 intramolecular cyclic and acyclic perfluoroalkylation of (hetero)arenes
 using X(CF2)4X
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              24862
_journal_page_last               24866
_journal_paper_doi               10.1039/D0RA05295G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         '0.5(C26 H14 F16 N2)'
_chemical_formula_sum            'C13 H7 F8 N'
_chemical_formula_weight         329.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1069(9)
_cell_length_b                   6.8506(6)
_cell_length_c                   13.7875(12)
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      3.2580
_cell_volume                     1237.98(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
  2  \w    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0055181000
_diffrn_orient_matrix_UB_12      -0.0065695000
_diffrn_orient_matrix_UB_13      0.0510798000
_diffrn_orient_matrix_UB_21      -0.0536812000
_diffrn_orient_matrix_UB_22      -0.0072805000
_diffrn_orient_matrix_UB_23      0.0050021000
_diffrn_orient_matrix_UB_31      0.0034910000
_diffrn_orient_matrix_UB_32      -0.1031355000
_diffrn_orient_matrix_UB_33      -0.0036259000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.955
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0520P)^2^+0.2960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra05295g2.cif
_cod_data_source_block           7a
_cod_depositor_comments
'Adding full bibliography for 7240808--7240811.cif.'
_cod_database_code               7240810
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     'Cui methylindole Cyclicperfluoroalkylation'
_diffrn_oxdiff_ac3_digest_frames
;
01b263afbe41efe93db275c1d0ebd0a7a600386f4cd
;
_diffrn_oxdiff_ac3_digest_hkl
;
01c50784b16bcf86964afc2c1b772243b53fbc
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
F8 \\sim C7 \\sim C8 \\sim C10 \\sim C13 \\sim F1 \\sim F4 \\sim F6 \\sim C12
\\sim C11 \\sim F7 \\sim F5 \\sim F2 \\sim F3 \\sim C8 \\sim C7 \\sim C13 \\sim
C8 \\sim C10 \\sim C7 \\sim F7 \\sim C13 \\sim F8 \\sim C13 \\sim C12 \\sim C13
\\sim F1 \\sim C10 \\sim F2 \\sim C10 \\sim C11 \\sim C10 \\sim F6 \\sim C12
\\sim C12 \\sim C11 \\sim F5 \\sim C12 \\sim F4 \\sim C11 \\sim F3 \\sim C11:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F8(0.5) C10(0.5) F1(0.5) H9A(0.5) H9B(0.5) H9C(0.5) F4(0.5)
 F6(0.5) C12(0.5) C11(0.5) F7(0.5) F5(0.5) F2(0.5) F3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.883