Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C-H Amidation.
Liang, Dongdong; Yu, Wenbo; Nguyen, Nam; Deschamps, Jeffrey R.; Imler, Gregory H.; Li, Yue; MacKerell, Jr, Alexander D; Jiang, Chao; Xue, Fengtian; The Journal of organic chemistry 82 (2017) 3589–3596; doi:10.1021/acs.joc.7b00106

data_4032378
_publ_section_title
;
 Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C-H
 Amidation.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3589
_journal_page_last               3596
_journal_paper_doi               10.1021/acs.joc.7b00106
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C14 H10 F N O2'
_chemical_formula_sum            'C14 H10 F N O2'
_chemical_formula_weight         243.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.134(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.2186(9)
_cell_length_b                   9.333(2)
_cell_length_c                   13.852(3)
_cell_measurement_reflns_used    1727
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.3575
_cell_measurement_theta_min      2.6325
_cell_volume                     544.6(2)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w 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  0.0260
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4850
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.633
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0368P)^2^+0.0151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.837
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                1688
_reflns_number_total             2041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00106_si_004.cif
_cod_data_source_block           xue040
_cod_depositor_comments
'Adding full bibliography for 4032377--4032380.cif.'
_cod_database_code               4032378
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.994