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_4032377
_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         'C15 H10 F3 N O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24
_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                 99.6040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6464(5)
_cell_length_b                   5.6834(3)
_cell_length_c                   12.7817(7)
_cell_measurement_reflns_used    3704
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.51
_cell_volume                     619.30(6)
_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 0.917
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.917
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3568
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         3.507
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       rod
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1789
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.0463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_full    0.637
_reflns_Friedel_fraction_max     0.630
_reflns_number_gt                1785
_reflns_number_total             1789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00106_si_006.cif
_cod_data_source_block           xue043
_cod_depositor_comments
'Adding full bibliography for 4032377--4032380.cif.'
_cod_database_code               4032377
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.913