Highly Enantioselective Synthesis of 2,3-Dihydroquinazolinones through Intramolecular Amidation of Imines.
Prakash, Muthuraj; Kesavan, Venkitasamy; Organic letters 14 (2012) 1896–1899; doi:10.1021/ol300518m

data_1507599
_publ_section_title
;
 Highly Enantioselective Synthesis of 2,3-Dihydroquinazolinones through
 Intramolecular Amidation of Imines.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1896
_journal_page_last               1899
_journal_paper_doi               10.1021/ol300518m
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 98.727(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.7827(18)
_cell_length_b                   11.5084(10)
_cell_length_c                   11.8588(7)
_cell_measurement_reflns_used    3028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.75
_cell_volume                     2803.5(4)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7922
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+1.9262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                3015
_reflns_number_total             3584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300518m_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1507599