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_1556247
_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 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.45
_chemical_melting_point          416(2)
_chemical_name_systematic
; 
(Z)-2-tert-butyl-4-((4-nitrophenyl)(phenyl)methylene)
-4H-benzo[d][1,3]oxazine
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.2730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.98980(10)
_cell_length_b                   19.4167(5)
_cell_length_c                   18.1253(4)
_cell_measurement_reflns_used    5870
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      69.91
_cell_measurement_theta_min      6.72
_cell_volume                     2086.07(8)
_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 0.929
_diffrn_measured_fraction_theta_max 0.929
_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  0.0775
_diffrn_reflns_av_sigmaI/netI    0.1037
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9647
_diffrn_reflns_theta_full        55.08
_diffrn_reflns_theta_max         55.08
_diffrn_reflns_theta_min         6.72
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0634P)^2^+0.0723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                1507
_reflns_number_total             2451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402600r_si_003.cif
_cod_data_source_block           3j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556247
_iucr_refine_reflections_details 3j.hkl