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_4033779
_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         'C22 H18 Br N O2'
_chemical_formula_sum            'C22 H18 Br N O2'
_chemical_formula_weight         408.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-03
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
_cell_angle_beta                 104.568(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6497(6)
_cell_length_b                   20.2453(10)
_cell_length_c                   9.9639(6)
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0550
_cell_measurement_theta_min      3.9400
_cell_volume                     1883.98(19)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2542
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details
;
  1 omega   37.00   83.00   1.0000   59.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4644  178.0000 -180.0000 46

  2 omega  -13.00   37.00   1.0000   59.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4644   19.0000 -120.0000 50

  3 omega  -17.00   54.00   1.0000   59.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4644  -99.0000 -120.0000 71

  4 omega   25.00   73.00   1.0000   59.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4644   57.0000  -60.0000 48

  5 omega  -36.00   -6.00   1.0000   59.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.6988   37.0000   60.0000 30
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_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0126563000
_diffrn_orient_matrix_UB_12      0.0265750000
_diffrn_orient_matrix_UB_13      0.0479019000
_diffrn_orient_matrix_UB_21      0.0746463000
_diffrn_orient_matrix_UB_22      -0.0060643000
_diffrn_orient_matrix_UB_23      0.0145221000
_diffrn_orient_matrix_UB_31      0.0054078000
_diffrn_orient_matrix_UB_32      0.0220313000
_diffrn_orient_matrix_UB_33      -0.0538856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9704
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description
;
;
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.7137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2567
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03193_si_002.cif
_cod_data_source_block           sxj-j-593
_cod_original_cell_volume        1883.97(19)
_cod_database_code               4033779
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N Br'
_shelx_estimated_absorpt_t_max   0.644
_shelx_estimated_absorpt_t_min   0.599
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), N1(H1)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'