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_7240811
_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         'C14 H12 F8 O2'
_chemical_formula_sum            'C14 H12 F8 O2'
_chemical_formula_weight         364.24
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-07
_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                 94.317(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7335(7)
_cell_length_b                   19.260(2)
_cell_length_c                   15.5646(18)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.0740
_cell_measurement_theta_min      3.3880
_cell_volume                     2909.6(5)
_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_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_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   40.00    --   30.00  54.00  30.00  193
  2  \w    -71.00 111.00   1.00   40.00    --   30.00  54.00-180.00  182
  3  \w    -59.00 -32.00   1.00   40.00    --   30.00  54.00  30.00   27
;
_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      0.0406259000
_diffrn_orient_matrix_UB_12      0.0221616000
_diffrn_orient_matrix_UB_13      -0.0242765000
_diffrn_orient_matrix_UB_21      -0.0172254000
_diffrn_orient_matrix_UB_22      0.0285785000
_diffrn_orient_matrix_UB_23      0.0257668000
_diffrn_orient_matrix_UB_31      0.0582830000
_diffrn_orient_matrix_UB_32      -0.0069766000
_diffrn_orient_matrix_UB_33      0.0288758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0587
_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       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20021
_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         26.372
_diffrn_reflns_theta_min         2.489
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64598
_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    1.663
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0830P)^2^+1.3320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3793
_reflns_number_total             5937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra05295g2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7240808--7240811.cif.'
_cod_original_cell_volume        2909.5(5)
_cod_database_code               7240811
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     'ono114 Cui 14diethoxybenzene cyclic'
_diffrn_oxdiff_ac3_digest_frames
;
01468f81c44acc098743bb34c2a6691d8a004024540
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a45ac8e85e18eec2d1874918b0497129b79a
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C9A(H9AA,H9AB), C7B(H7BA,H7BB), C9B(H9BA,H9BB)
2.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C2B(H2B), C3B(H3B)
2.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C10A(H10A,H10B,H10C), C8B(H8BA,H8BB,H8BC), C10B(H10D,
 H10E,H10F)
;
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.802