Enantioselective Synthesis of Atropisomeric Benzamides through Peptide-Catalyzed Bromination
Kimberly T. Barrett; Scott J. Miller; Journal of the American Chemical Society 135 (2013) 2963–2966; doi:10.1021/ja400082x

data_4119395
_publ_section_title
;
 Enantioselective Synthesis of Atropisomeric Benzamides through
 Peptide-Catalyzed Bromination
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2963
_journal_page_last               2966
_journal_paper_doi               10.1021/ja400082x
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'Br3 O2 N C14 H18'
_chemical_formula_sum            'C14 H18 Br3 N O2'
_chemical_formula_weight         472.01
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.6495(14)
_cell_length_b                   9.4852(18)
_cell_length_c                   24.586(4)
_cell_measurement_reflns_used    7511
_cell_measurement_temperature    223
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      3.13
_cell_volume                     1783.9(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD (SCX mini)'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8639
_diffrn_reflns_theta_full        24.36
_diffrn_reflns_theta_max         24.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.805
_exptl_absorpt_correction_T_max  0.256
_exptl_absorpt_correction_T_min  0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       Prism
_exptl_crystal_F_000             920.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.860
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1196 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0416P)^2^+2.4104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2320
_reflns_number_total             2895
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja400082x_si_003.cif
_cod_data_source_block           '_User-defined'
_cod_original_formula_sum        'Br3 O2 N C14 H18'
_cod_database_code               4119395