Palladium-Catalyzed C-N Bond Cleavage of 2 H-Azirines for the Synthesis of Functionalized α-Amido Ketones.
Xu, Fen; Si, Xiao-Ju; Song, Yuan-Yuan; Wang, Xing-Dong; Liu, Chun-Sen; Geng, Peng-Fei; Du, Miao; The Journal of organic chemistry 84 (2019) 2200–2208; doi:10.1021/acs.joc.8b03193

data_4033782
_publ_section_title
;
 Palladium-Catalyzed C-N Bond Cleavage of 2 H-Azirines for the Synthesis
 of Functionalized \a-Amido Ketones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2200
_journal_page_last               2208
_journal_paper_doi               10.1021/acs.joc.8b03193
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C23 H15 F6 N O2'
_chemical_formula_sum            'C23 H15 F6 N O2'
_chemical_formula_weight         451.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                74.933(8)
_cell_angle_beta                 75.154(9)
_cell_angle_gamma                63.737(10)
_cell_formula_units_Z            4
_cell_length_a                   11.1320(12)
_cell_length_b                   11.8213(11)
_cell_length_c                   18.4912(16)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      72.7470
_cell_measurement_theta_min      4.4310
_cell_volume                     2078.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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    -56.00  33.00   1.00    5.59    --  -40.30  57.00   0.00   89
  2  \w      2.00  76.00   1.00    5.59    --   40.30 -99.00  90.00   74
  3  \w     25.00 109.00   1.00   22.35    --  107.14 -95.00 -30.00   84
  4  \w     87.00 113.00   1.00   22.35    --  107.14 -61.00 -90.00   26
  5  \w     55.00  95.00   1.00    5.59    --   40.30-125.00-150.00   40
  6  \w     37.00  62.00   1.00   22.35    --  107.14 -61.00 -90.00   25
  7  \w     46.00 121.00   1.00   22.35    --  107.14 -30.00 -90.00   75
  8  \w    110.00 147.00   1.00   22.35    --  107.14  30.00 -30.00   37
  9  \w     79.00 178.00   1.00   22.35    --  107.14  30.00  90.00   99
 10  \w     87.00 140.00   1.00   22.35    --  107.14 -77.00  90.00   53
 11  \w     82.00 109.00   1.00   22.35    --  107.14 -95.00  90.00   27
 12  \w     43.00 117.00   1.00   22.35    --  107.14 -45.00  30.00   74
 13  \w     49.00 121.00   1.00   22.35    --  107.14-125.00 -60.00   72
 14  \w     40.00 102.00   1.00   22.35    --  107.14 -95.00  60.00   62
 15  \w     33.00 126.00   1.00   22.35    --  107.14 -30.00 150.00   93
 16  \w     83.00 135.00   1.00   22.35    --  107.14  45.00-180.00   52
 17  \w    138.00 167.00   1.00   22.35    --  107.14  45.00-180.00   29
 18  \w   -108.00 -11.00   1.00    5.59    --  -40.30 -77.00 150.00   97
 19  \w   -115.00 -16.00   1.00    5.59    --  -40.30 -38.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1123301000
_diffrn_orient_matrix_UB_12      0.0105750000
_diffrn_orient_matrix_UB_13      0.0286846000
_diffrn_orient_matrix_UB_21      0.0226913000
_diffrn_orient_matrix_UB_22      -0.1288218000
_diffrn_orient_matrix_UB_23      0.0538018000
_diffrn_orient_matrix_UB_31      0.1064520000
_diffrn_orient_matrix_UB_32      -0.0709424000
_diffrn_orient_matrix_UB_33      -0.0626900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.841
_diffrn_reflns_theta_min         4.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0705
_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^)+(0.1256P)^2^+0.3161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5745
_reflns_number_total             8104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03193_si_003.cif
_cod_data_source_block           sxj-20180412-j-579
_cod_database_code               4033782
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C N O H F'
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.759
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C30(H30), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C26(H26), C41(H41), C6(H6), C18(H18), C43(H43), C37(H37),
 C28(H28), C33(H33), C42(H42), C20(H20), C10(H10), C25(H25), C19(H19), C14(H14),
  C24(H24), C5(H5), C2(H2A), C35(H35), C36(H36), C12(H12), C29(H29), C4(H4),
 C11(H11), C34(H34), C13(H13), C3(H3)
;
_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 2.441
_oxdiff_exptl_absorpt_empirical_full_min 0.686