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_4033780
_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         'C16 H12 F3 N O2'
_chemical_formula_sum            'C16 H12 F3 N O2'
_chemical_formula_weight         307.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2120(6)
_cell_length_b                   9.2803(3)
_cell_length_c                   10.3264(3)
_cell_measurement_reflns_used    2103
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3130
_cell_measurement_theta_min      4.7400
_cell_volume                     1457.80(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.978
_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    -70.00  -5.00   1.00    1.50    --  -40.55 -19.00   0.00   65
  2  \w   -111.00 -26.00   1.00    1.50    --  -40.55 -38.00 -30.00   85
  3  \w     66.00  96.00   1.00    4.00    --  107.14 -61.00  30.00   30
  4  \w     56.00  88.00   1.00    4.00    --  107.14  15.00 -60.00   32
  5  \w    107.00 174.00   1.00    4.00    --  107.14  15.00 -60.00   67
  6  \w    103.00 171.00   1.00    4.00    --  107.14 125.00-180.00   68
  7  \w     91.00 167.00   1.00    4.00    --  107.14  45.00   0.00   76
;
_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      0.1266705000
_diffrn_orient_matrix_UB_12      0.0514256000
_diffrn_orient_matrix_UB_13      0.0596383000
_diffrn_orient_matrix_UB_21      -0.1037089000
_diffrn_orient_matrix_UB_22      0.0747546000
_diffrn_orient_matrix_UB_23      0.0379408000
_diffrn_orient_matrix_UB_31      -0.0276854000
_diffrn_orient_matrix_UB_32      -0.0449396000
_diffrn_orient_matrix_UB_33      0.1313784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3446
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.708
_diffrn_reflns_theta_min         4.765
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74756
_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    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 571 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0471
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.418
_reflns_Friedel_fraction_full    0.493
_reflns_Friedel_fraction_max     0.461
_reflns_number_gt                2057
_reflns_number_total             2164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03193_si_004.cif
_cod_data_source_block           sxj-20180623-j-611
_cod_database_code               4033780
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N F'
_shelx_estimated_absorpt_t_max   0.807
_shelx_estimated_absorpt_t_min   0.777
_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:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_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 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.612