The palladium(ii)-catalyzed regioselective ortho-C-H bromination/iodination of arylacetamides with in situ generated imidic acid as the directing group: mechanistic exploration.
Jaiswal, Yogesh; Kumar, Yogesh; Kumar, Amit; Organic & biomolecular chemistry 17 (2019) 6809–6820; doi:10.1039/c9ob01082c

data_7156925
_publ_section_title
;
 The palladium(ii)-catalyzed regioselective ortho-C-H
 bromination/iodination of arylacetamides with in situ generated imidic
 acid as the directing group: mechanistic exploration.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6809
_journal_page_last               6820
_journal_paper_doi               10.1039/c9ob01082c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.346(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.336(7)
_cell_length_b                   4.975(2)
_cell_length_c                   16.193(8)
_cell_measurement_reflns_used    5550
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.555
_cell_measurement_theta_min      2.961
_cell_volume                     1108.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15699
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.555
_diffrn_reflns_theta_max         24.555
_diffrn_reflns_theta_min         2.961
_exptl_absorpt_coefficient_mu    2.861
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0499P)^2^+3.3221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01082c2.cif
_cod_data_source_block           M_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156924--7156925.cif.'
_cod_original_cell_volume        1108.3(9)
_cod_database_code               7156925
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.481
_shelx_estimated_absorpt_t_max   0.598
_shelx_res_checksum              76158