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_7240808
_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         'C12 H8 F8 O2'
_chemical_formula_sum            'C12 H8 F8 O2'
_chemical_formula_weight         336.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-26
_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                 95.319(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8488(11)
_cell_length_b                   11.665(2)
_cell_length_c                   15.489(2)
_cell_measurement_reflns_used    893
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.6170
_cell_measurement_theta_min      3.4280
_cell_volume                     1232.1(3)
_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_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   95.00    --   30.00  54.00 150.00  193
  2  \w    -74.00 119.00   1.00   95.00    --   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      -0.0063068000
_diffrn_orient_matrix_UB_12      -0.0484319000
_diffrn_orient_matrix_UB_13      0.0273185000
_diffrn_orient_matrix_UB_21      0.0787810000
_diffrn_orient_matrix_UB_22      -0.0260777000
_diffrn_orient_matrix_UB_23      -0.0193533000
_diffrn_orient_matrix_UB_31      0.0676364000
_diffrn_orient_matrix_UB_32      0.0260791000
_diffrn_orient_matrix_UB_33      0.0314880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1947
_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         26.367
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58936
_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    1.812
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.840
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0840P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1031
_reflns_number_total             1947
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9575\% 
 around [0.00 -0.00 1.00] (reciprocal) or [0.20 0.00 0.98] (direct)
;
_cod_data_source_file            d0ra05295g2.cif
_cod_data_source_block           twin_1a
_cod_depositor_comments
'Adding full bibliography for 7240808--7240811.cif.'
_cod_original_cell_volume        1232.1(4)
_cod_database_code               7240808
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     'Cui 14diMeObenz cyclicperfluoro'
_diffrn_oxdiff_ac3_digest_frames
;
013c857432b67a020773a68214c6886bf0003866068
;
_diffrn_oxdiff_ac3_digest_hkl
;
011d3f8515c2ab83db74fd6e918c835049299b
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.673(2)
 0.327(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2