Enantioselective bromination of axially chiral cyanoarenes in the presence of bifunctional organocatalysts
Wada, Yuuki; Matsumoto, Akira; Asano, Keisuke; Matsubara, Seijiro; RSC Advances 9 (2019) 31654–; doi:10.1039/C9RA05532K

data_7234396
_publ_section_title
;
 Enantioselective bromination of axially chiral cyanoarenes in the
 presence of bifunctional organocatalysts
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              31654
_journal_paper_doi               10.1039/C9RA05532K
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C19 H12 Br3 N O'
_chemical_formula_sum            'C19 H12 Br3 N O'
_chemical_formula_weight         510.02
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-06-25 deposited with the CCDC.    2019-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.052(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.3302(14)
_cell_length_b                   7.9001(9)
_cell_length_c                   18.630(2)
_cell_measurement_reflns_used    10727
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1804.6(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13812
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.731
_exptl_absorpt_correction_T_max  0.546
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             984.00
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.380
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3336 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.020(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7729
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0284P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                4766
_reflns_number_total             7729
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9ra05532k2.cif
_cod_data_source_block           2018_10_17_1_B
_cod_original_cell_volume        1804.6(4)
_cod_database_code               7234396