Palladium-Catalyzed Regioselective Carbonylation of C-H Bonds of N-Alkyl Anilines for Synthesis of Isatoic Anhydrides
Zheng-Hui Guan; Ming Chen; Zhi-Hui Ren; Journal of the American Chemical Society 134 (2012) 17490–17493; doi:10.1021/ja308976x

data_4118831
_publ_contact_author_name
;
;
_publ_section_title
;
 Palladium-Catalyzed Regioselective Carbonylation of C-H Bonds of N-Alkyl
 Anilines for Synthesis of Isatoic Anhydrides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17490
_journal_page_last               17493
_journal_paper_doi               10.1021/ja308976x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C50 H46 Br2 N2 P2 Pd2'
_chemical_formula_sum            'C50 H46 Br2 N2 P2 Pd2'
_chemical_formula_weight         1115.36
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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  1 omega  -14.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 38

  2 omega  -81.00  -43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 38

  3 omega  -68.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 34

  4 omega  -68.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 31

  5 omega -130.00  -27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000 -150.0000 103

  6 omega -122.00  -83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000    0.0000 39

  7 omega  -48.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   25.0000    0.0000 59

  8 omega  -87.00   -5.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   63.0000    0.0000 82

  9 omega  -43.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   38.0000  120.0000 52

 10 omega   54.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  150.0000 50

 11 omega   45.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -120.0000 53

 12 omega  128.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 42

 13 omega   47.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 40

 14 omega   90.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  -30.0000 87

 15 omega  110.00  141.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   60.0000 31

 16 omega   56.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   30.0000 37

 17 omega   72.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -90.0000 26

 18 omega   60.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   30.0000 32

 19 omega   62.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 52

 20 omega  153.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   60.0000 25

 21 omega   43.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   90.0000 42

 22 omega  100.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1088684000
_diffrn_orient_matrix_UB_12      0.0220136000
_diffrn_orient_matrix_UB_13      -0.0441469000
_diffrn_orient_matrix_UB_21      0.1009492000
_diffrn_orient_matrix_UB_22      -0.0384559000
_diffrn_orient_matrix_UB_23      0.0352188000
_diffrn_orient_matrix_UB_31      -0.0435019000
_diffrn_orient_matrix_UB_32      -0.0342712000
_diffrn_orient_matrix_UB_33      -0.0678399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19472
_diffrn_reflns_theta_full        72.55
_diffrn_reflns_theta_max         72.55
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    8.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             2129
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.667
_refine_diff_density_min         -2.607
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9411
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+20.8826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                8324
_reflns_number_total             9411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja308976x_si_004.cif
_cod_data_source_block           guanzhhui_3
_cod_original_cell_volume        4816.94(13)
_cod_database_code               4118831
_chemical_oxdiff_formula         c1
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95