Synthesis of benzo[1,3]oxazines via copper(i)-catalyzed cascade annulation of nitriles, aldehydes and diaryliodonium salts
Sheng, Jinyu; Su, Xiang; Cao, Chengyao; Chen, Chao; Organic Chemistry Frontiers 3 (2016) 501–; doi:10.1039/C6QO00012F

data_1553418
_publ_section_title
;
 Synthesis of benzo[1,3]oxazines via copper(i)-catalyzed cascade
 annulation of nitriles, aldehydes and diaryliodonium salts
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              501
_journal_paper_doi               10.1039/C6QO00012F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C21 H15 Br F N O'
_chemical_formula_weight         396.24
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2015-08-28 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                96.05(3)
_cell_angle_beta                 99.59(3)
_cell_angle_gamma                101.21(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9396(12)
_cell_length_b                   11.302(2)
_cell_length_c                   13.413(3)
_cell_measurement_reflns_used    3034
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4282
_cell_measurement_theta_min      1.5557
_cell_volume                     862.0(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7905
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0689P)^2^+0.8767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1315
_reflns_number_gt                3496
_reflns_number_total             3856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00012f2.cif
_cod_data_source_block           b
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1553418