Rhodium(II)-catalyzed transannulation approach to <i>N</i>-fluoroalkylated indoles.
Bakhanovich, Olga; Klepetářová, Blanka; Beier, Petr; Organic & biomolecular chemistry 21 (2023) 7924–7927; doi:10.1039/d3ob01415k

data_7159571
_publ_section_title
;
 Rhodium(II)-catalyzed transannulation approach to
 <i>N</i>-fluoroalkylated indoles.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7924
_journal_page_last               7927
_journal_paper_doi               10.1039/d3ob01415k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C11 H6 F5 N O2'
_chemical_formula_sum            'C11 H6 F5 N O2'
_chemical_formula_weight         279.16
_chemical_name_systematic
'1-(perfluoroethyl)-1H-indole-2-carboxylic acid'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2023-08-28 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                107.8102(12)
_cell_angle_beta                 94.3444(13)
_cell_angle_gamma                95.6658(13)
_cell_formula_units_Z            2
_cell_length_a                   7.6612(3)
_cell_length_b                   8.6533(3)
_cell_length_c                   8.7731(3)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    180
_cell_measurement_theta_max      68.1760
_cell_measurement_theta_min      5.3293
_cell_volume                     547.57(3)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Unknown
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  Unknown
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15955
_diffrn_reflns_theta_full        66.850
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         5.329
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.557
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       21(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.0047659
_refine_ls_shift/su_mean         0.0008702
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method = Chebychev polynomial, (Carruthers & Watkin, 1979) 
 W = 1.0/[A[0]*T[0]'(X)+A[1]*T[1]'(X) ... +A[NP-1]*T[NP-1]'(X)] 
 0.298 0.393 0.123 0.970E-03 -0.156E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0555
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0555
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1887
_reflns_number_total             2004
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.05
_oxford_diffrn_Wilson_scale      7.52
_oxford_refine_ls_r_factor_ref   0.0438
_oxford_refine_ls_scale          0.3947(13)
_oxford_reflns_number_all        2004
_cod_data_source_file            d3ob01415k2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159571.cif.
;
_cod_database_code               7159571
_oxford_refine_reflns_threshold_expression I>2.0\s(I)
_oxford_refine_ls_r_factor_all   0.0464
_oxford_refine_ls_wr_factor_all  0.0613