Bifunctional organocatalysts for the enantioselective synthesis of axially chiral isoquinoline N-oxides.
Miyaji, Ryota; Asano, Keisuke; Matsubara, Seijiro; Journal of the American Chemical Society 137 (2015) 6766–6769; doi:10.1021/jacs.5b04151

data_4123709
_publ_section_title
;
 Bifunctional organocatalysts for the enantioselective synthesis of
 axially chiral isoquinoline N-oxides.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6766
_journal_page_last               6769
_journal_paper_doi               10.1021/jacs.5b04151
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C15 H8 Br3 N O2'
_chemical_formula_sum            'C15 H8 Br3 N O2'
_chemical_formula_weight         473.95
_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                   7.4600(10)
_cell_length_b                   9.0181(12)
_cell_length_c                   22.359(3)
_cell_measurement_reflns_used    14759
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.29
_cell_volume                     1504.2(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    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0584
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16000
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.071
_exptl_absorpt_correction_T_max  0.113
_exptl_absorpt_correction_T_min  0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             904.00
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.620
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1450 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.004(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                3043
_reflns_number_total             3448
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja5b04151_si_002.cif
_cod_data_source_block           User-defined
_cod_depositor_comments
'Adding full bibliography for 4123708--4123709.cif.'
_cod_original_cell_volume        1504.2(4)
_cod_database_code               4123709