Synthesis of Dibenzosuberones Bearing an Isoxazole Group via Palladium-Catalyzed Intramolecular C-H/C-Br Bond Cross-Coupling of Ortho-Aroylated 3,5-Diarylisoxazoles.
Chao, Tung; Su, Zhe-Hong; Yen, Ko-Wang; Wu, Ming-Jung; Chu, Jean-Ho; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00346

data_4038182
_publ_section_title
;
 Synthesis of Dibenzosuberones Bearing an Isoxazole Group via
 Palladium-Catalyzed Intramolecular C-H/C-Br Bond Cross-Coupling of
 Ortho-Aroylated 3,5-Diarylisoxazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00346
_journal_year                    2020
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.142(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8053(6)
_cell_length_b                   13.7494(8)
_cell_length_c                   23.7333(14)
_cell_measurement_reflns_used    6934
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.959
_cell_measurement_theta_min      2.274
_cell_volume                     3181.3(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47262
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+1.1186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                3594
_reflns_number_total             5645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00346_si_007.cif
_cod_data_source_block           d21233
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038182