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_4124597
_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_absolute_configuration ad
_chemical_formula_moiety         'C27 H49 N6 O6.50'
_chemical_formula_sum            'C27 H49 N6 O6.5'
_chemical_formula_weight         561.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.716(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1717(11)
_cell_length_b                   9.3641(6)
_cell_length_c                   21.5606(15)
_cell_measurement_reflns_used    -189
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      2.8
_cell_volume                     3157.9(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1358
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            80164
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         2.825
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 2860 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         11274
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1113P)^2^+0.3367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1864
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                8029
_reflns_number_total             11274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07726_si_002.cif
_cod_data_source_block           007-15050
_cod_original_formula_sum        'C27 H49 N6 O6.50'
_cod_database_code               4124597
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              93828
_shelx_hkl_checksum              36531