Copper-Catalyzed Selective ortho-C-H/N-H Annulation of Benzamides with Arynes: Synthesis of Phenanthridinone Alkaloids.
Zhang, Ting-Yu; Lin, Jun-Bing; Li, Quan-Zhe; Kang, Jun-Chen; Pan, Jin-Long; Hou, Si-Hua; Chen, Chao; Zhang, Shu-Yu; Organic letters 19 (2017) 1764–1767; doi:10.1021/acs.orglett.7b00442

data_1545958
_publ_section_title
;
 Copper-Catalyzed Selective ortho-C-H/N-H Annulation of Benzamides with
 Arynes: Synthesis of Phenanthridinone Alkaloids.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1764
_journal_page_last               1767
_journal_paper_doi               10.1021/acs.orglett.7b00442
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H13 F3 N2 O'
_chemical_formula_sum            'C23 H13 F3 N2 O'
_chemical_formula_weight         390.35
_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
_cell_angle_alpha                90
_cell_angle_beta                 105.554(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6208(3)
_cell_length_b                   21.2775(7)
_cell_length_c                   11.1815(4)
_cell_measurement_reflns_used    8642
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.60
_cell_volume                     1746.70(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13194
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.286
_diffrn_reflns_theta_min         4.601
_exptl_absorpt_coefficient_mu    0.966
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0760P)^2^+0.8693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2756
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00442_si_003.cif
_cod_data_source_block           t_0m
_cod_database_code               1545958
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.830
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              12339
_shelx_hkl_checksum              35948