Copper-catalyzed oxidative ring closure and carboarylation of 2-ethynylanilides.
Sinai, Ádám; Mészáros, Ádám; Gáti, Tamás; Kudar, Veronika; Palló, Anna; Novák, Zoltán; Organic letters 15 (2013) 5654–5657; doi:10.1021/ol402600r

data_1556248
_publ_section_title
;
 Copper-catalyzed oxidative ring closure and carboarylation of
 2-ethynylanilides.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5654
_journal_page_last               5657
_journal_paper_doi               10.1021/ol402600r
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C25 H21 F2 N O'
_chemical_formula_sum            'C25 H21 F2 N O'
_chemical_formula_weight         389.43
_chemical_melting_point          397(2)
_chemical_name_systematic
; 
4-(bis(4-fluorophenyl)methylene)-2-tert-butyl
-2,4-dihydro-1H-benzo[d][1,3]oxazine
;
_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_Hall  '-P 1'
_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
_cell_angle_alpha                75.170(2)
_cell_angle_beta                 88.700(2)
_cell_angle_gamma                85.311(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0188(2)
_cell_length_b                   9.7294(3)
_cell_length_c                   17.4629(6)
_cell_measurement_reflns_used    2991
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.06
_cell_measurement_theta_min      7.39
_cell_volume                     985.24(6)
_computing_cell_refinement
;
'CrystalClear (Rigaku/MSC Inc., 2006)'          
;
_computing_data_collection
;
'CrystalClear (Rigaku/MSC Inc., 2006)'          
;
_computing_data_reduction
;
'CrystalClear (Rigaku/MSC Inc., 2006)'          
;
_computing_molecular_graphics
;
'ORTEP-3 for Windows (Farrugia, 1997)' 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6765
_diffrn_reflns_theta_full        51.14
_diffrn_reflns_theta_max         51.14
_diffrn_reflns_theta_min         7.38
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.0023(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0741
_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^)+(0.1225P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.2521
_reflns_number_gt                1070
_reflns_number_total             1936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402600r_si_002.cif
_cod_data_source_block           3gg
_cod_database_code               1556248
_iucr_refine_reflections_details 3aa.hkl