Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C–H Activation–Lossen Rearrangement–Wallach Reaction
Tan, Jin-Fay; Bormann, Carl Thomas; Severin, Kay; Cramer, Nicolai; ACS Catalysis 10 (2020) 3790–3796; doi:10.1021/acscatal.0c00499

data_4517482
_publ_section_title
;
 Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to
 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C--H Activation--Lossen
 Rearrangement--Wallach Reaction
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3790
_journal_page_last               3796
_journal_paper_doi               10.1021/acscatal.0c00499
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 F N O'
_chemical_formula_sum            'C18 H14 F N O'
_chemical_formula_weight         279.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                109.851(3)
_cell_angle_beta                 92.169(3)
_cell_angle_gamma                112.466(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2367(3)
_cell_length_b                   11.4102(4)
_cell_length_c                   13.7829(5)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    140.00(11)
_cell_measurement_theta_max      72.6110
_cell_measurement_theta_min      3.4570
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_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
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_computing_molecular_graphics    'Mercury 4.1.2 (CCDC, 2019)'
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_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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    -77.00  45.00   1.00    2.00    --  -40.91   0.00 150.00  122
  2  \w   -107.00 -66.00   1.00    2.00    --  -40.91-138.00  51.00   41
  3  \w    -46.00  22.00   1.00    2.00    --  -40.91  38.00  30.00   68
  4  \w     36.00  72.00   1.00    2.00    --   40.91-125.00 -60.00   36
  5  \w     31.00  93.00   1.00    2.00    --   40.91-125.00 150.00   62
  6  \w     58.00  88.00   1.00    8.00    --  105.15 178.00 150.00   30
  7  \w    101.00 178.00   1.00    8.00    --  105.15 111.00-120.00   77
  8  \w     36.00  64.00   1.00    8.00    --  105.15 -61.00 -30.00   28
  9  \w     32.00 133.00   1.00    8.00    --  105.15 -77.00-150.00  101
 10  \w     29.00  91.00   1.00    8.00    --  105.15-111.00  60.00   62
 11  \w     78.00 173.00   1.00    8.00    --  105.15  30.00   0.00   95
 12  \w    135.00 160.00   1.00    8.00    --  105.15 111.00 -90.00   25
 13  \w    140.00 174.00   1.00    8.00    --  105.15  30.00 -60.00   34
 14  \w     85.00 111.00   1.00    8.00    --  105.15  30.00 -60.00   26
 15  \w     87.00 112.00   1.00    8.00    --  105.15-111.00 -30.00   25
 16  \w     29.00  86.00   1.00    8.00    --  105.15 -30.00   0.00   57
 17  \w     30.00 123.00   1.00    8.00    --  105.15 -30.00-180.00   93
 18  \w     60.00 110.00   1.00    8.00    --  105.15-111.00  90.00   50
 19  \w     35.00 120.00   1.00    8.00    --  105.15-131.00-133.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.752
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         5303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0727P)^2^+0.2069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4732
_reflns_number_total             5303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00499_si_002.cif
_cod_data_source_block           jft-1-414
_cod_depositor_comments
;Adding full bibliography for 4517481--4517482.cif.

 Adding full bibliography for 4517481--4517482.cif.
;
_cod_original_cell_volume        1373.04(9)
_cod_database_code               4517482
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.668
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              28607
_shelx_hkl_checksum              19583