Electrochemically enabled functionalization of indoles or anilines for the synthesis of hexafluoroisopropoxy indole and aniline derivatives.
Mo, Zu-Yu; Wang, Xin-Yu; Zhang, Yu-Zhen; Yang, Li; Tang, Hai-Tao; Pan, Ying-Ming; Organic & biomolecular chemistry 18 (2020) 3832–3837; doi:10.1039/d0ob00157k

data_7157488
_publ_section_title
;
 Electrochemically enabled functionalization of indoles or anilines for
 the synthesis of hexafluoroisopropoxy indole and aniline derivatives.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3832
_journal_page_last               3837
_journal_paper_doi               10.1039/d0ob00157k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C16 H10 Cl F12 N O3'
_chemical_formula_sum            'C16 H10 Cl F12 N O3'
_chemical_formula_weight         527.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.189(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7099(6)
_cell_length_b                   16.5285(15)
_cell_length_c                   15.8165(16)
_cell_measurement_reflns_used    4429
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3160
_cell_measurement_theta_min      3.6010
_cell_volume                     2010.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -20.00  60.00   1.00   15.00    --   17.93 -99.00   0.00   80
  2  \w    -55.00  91.00   1.00   15.00    --   17.93   0.00-180.00  146
  3  \w    -96.00 -35.00   1.00   15.00    --  -19.72-178.00 150.00   61
  4  \w    -92.00 -44.00   1.00   15.00    --  -19.72 -38.00-120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0814085000
_diffrn_orient_matrix_UB_12      -0.0149628000
_diffrn_orient_matrix_UB_13      0.0113607000
_diffrn_orient_matrix_UB_21      0.0382585000
_diffrn_orient_matrix_UB_22      -0.0105171000
_diffrn_orient_matrix_UB_23      0.0406806000
_diffrn_orient_matrix_UB_31      -0.0209997000
_diffrn_orient_matrix_UB_32      0.0387889000
_diffrn_orient_matrix_UB_33      0.0153525000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11847
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+1.0065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                2975
_reflns_number_total             3944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob00157k2.cif
_cod_data_source_block           20200428-pym-mzy-claaa
_cod_depositor_comments          'Adding full bibliography for 7157488.cif.'
_cod_database_code               7157488
_reflns_odcompleteness_completeness 99.53
_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.a Ternary CH refined with riding coordinates:
 C14(H14), C2(H2), C1(H1), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.589