Direct Synthesis of Polysubstituted Quinoline Derivatives by InBr~3~-Promoted Dimerization of 2-Ethynylaniline Derivatives
Norio Sakai; Kimiyoshi Annaka; Takeo Konakahara; Journal of Organic Chemistry 71 (2006) 3653–3655; doi:10.1021/jo060245f

data_4021665
_publ_section_title
;
 Direct Synthesis of Polysubstituted Quinoline Derivatives by
 InBr~3~-Promoted Dimerization of 2-Ethynylaniline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3653
_journal_page_last               3655
_journal_paper_doi               10.1021/jo060245f
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7558(9)
_cell_length_b                   9.0365(9)
_cell_length_c                   26.814(3)
_cell_measurement_temperature    273(2)
_cell_volume                     2363.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12610
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.069
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+2.0400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1714
_reflns_number_gt                2377
_reflns_number_total             2763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060245fsi20060206_095028.cif
_cod_database_code               4021665