Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives.
Villuri, Bharath Kumar; Ichake, Sachin S.; Reddy, Sabbasani Rajasekhara; Kavala, Veerababurao; Bandi, Vijayalakshmi; Kuo, Chun-Wei; Yao, Ching-Fa; The Journal of organic chemistry 83 (2018) 10241–10247; doi:10.1021/acs.joc.8b01443

data_4035024
_publ_section_title
;
 Copper-Catalyzed Cascade Synthesis of 2-Aryl-3-cyanobenzofuran and
 Dibenzo[ b, f]oxepine-10-carbonitrile Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10241
_journal_page_last               10247
_journal_paper_doi               10.1021/acs.joc.8b01443
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H8 F N O'
_chemical_formula_sum            'C15 H8 F N O'
_chemical_formula_weight         237.22
_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                 92.452(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7895(8)
_cell_length_b                   21.669(5)
_cell_length_c                   13.318(4)
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.758
_cell_measurement_theta_min      2.418
_cell_volume                     1092.6(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1485
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10716
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.047(8)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0673P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                1246
_reflns_number_total             1955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01443_si_001.cif
_cod_data_source_block           d19331
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035024