Synthesis of 2,3-Dihydroquinolin-4(1H)-ones through Catalytic Metathesis of o-Alkynylanilines and Aldehydes
Akio Saito; Jun Kasai; Yu Odaira; Haruhiko Fukaya; Yuji Hanzawa; Journal of Organic Chemistry 74 (2009) 5644–5647; doi:10.1021/jo900857c

data_4024699
_publ_section_title
;
Synthesis of 2,3-Dihydroquinolin-4(1H)-ones through Catalytic Metathesis
of o-Alkynylanilines and Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5644
_journal_page_last               5647
_journal_paper_doi               10.1021/jo900857c
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C24 H21 N O3'
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42
_space_group_IT_number           2
_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                89.696(3)
_cell_angle_beta                 71.752(3)
_cell_angle_gamma                65.373(3)
_cell_formula_units_Z            2
_cell_length_a                   8.654(3)
_cell_length_b                   9.142(3)
_cell_length_c                   13.383(4)
_cell_measurement_reflns_used    4492
_cell_measurement_temperature    90
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     904.4(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10340
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0632P)^2^+0.3661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                3452
_reflns_number_total             4098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900857c_si_002.cif
_cod_data_source_block           trans-2,3-ph-othq
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1      '
_cod_database_code               4024699