Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides.
Pintori, Didier G.; Greaney, Michael F.; Organic letters 12 (2010) 168–171; doi:10.1021/ol902568x

data_1503361
_publ_section_title
;
 Insertion of benzene rings into the amide bond: one-step synthesis of
 acridines and acridones from aryl amides.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              168
_journal_page_last               171
_journal_paper_doi               10.1021/ol902568x
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'Didier Pintori'
_chemical_formula_moiety         'C23 H16 I N O2'
_chemical_formula_sum            'C23 H16 I N O2'
_chemical_formula_weight         465.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.0787(12)
_cell_angle_beta                 79.3543(11)
_cell_angle_gamma                85.5743(11)
_cell_formula_units_Z            2
_cell_length_a                   8.3396(2)
_cell_length_b                   9.1524(2)
_cell_length_c                   12.1045(3)
_cell_measurement_reflns_used    6941
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.213
_cell_measurement_theta_min      2.236
_cell_volume                     903.91(4)
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16144
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         29.73
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    1.790
_exptl_absorpt_correction_T_max  0.7757
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method
'Evaporation of Pet ether/Et2O/DCM solution'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.4411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                4104
_reflns_number_total             4728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902568x_si_002.cif
_cod_data_source_block           mg9005
_cod_database_code               1503361