Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination.
Diener, Matthew E.; Metrano, Anthony J.; Kusano, Shuhei; Miller, Scott J.; Journal of the American Chemical Society 137 (2015) 12369–12377; doi:10.1021/jacs.5b07726

data_4124596
_publ_section_title
;
 Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via
 Peptide-Catalyzed Atroposelective Bromination.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12369
_journal_page_last               12377
_journal_paper_doi               10.1021/jacs.5b07726
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C15 H9 Br3 N2 O2'
_chemical_formula_weight         488.97
_space_group_IT_number           1
_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                72.352(5)
_cell_angle_beta                 73.504(5)
_cell_angle_gamma                63.788(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9891(2)
_cell_length_b                   9.6537(2)
_cell_length_c                   10.6551(8)
_cell_measurement_reflns_used    13159
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      4.4
_cell_volume                     778.24(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'microfocus rotaing anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26413
_diffrn_reflns_theta_full        68.07
_diffrn_reflns_theta_max         68.07
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    9.691
_exptl_absorpt_correction_T_max  0.8298
_exptl_absorpt_correction_T_min  0.4441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.897
_refine_diff_density_min         -1.184
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5237
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0561P)^2^+1.2205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                5140
_reflns_number_total             5237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b07726_si_003.cif
_cod_data_source_block           12108
_cod_original_cell_volume        778.24(6)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               4124596