Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives.
Hirata, Tomoaki; Takahashi, Isao; Suzuki, Yuya; Yoshida, Hiroaki; Hasegawa, Hiroshi; Kitagawa, Osamu; The Journal of organic chemistry 81 (2016) 318–323; doi:10.1021/acs.joc.5b02387

data_4036515
_publ_section_title
;
 Catalytic Enantioselective Synthesis of N-C Axially Chiral
 Phenanthridin-6-one Derivatives.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              318
_journal_page_last               323
_journal_paper_doi               10.1021/acs.joc.5b02387
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H20 Br N O'
_chemical_formula_sum            'C23 H20 Br N O'
_chemical_formula_weight         406.31
_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_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_creation_date             'June 12 2015'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-12 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.845(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4683(9)
_cell_length_b                   13.4256(19)
_cell_length_c                   11.0713(16)
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.42
_cell_volume                     941.0(2)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4514
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    2.195
_exptl_absorpt_correction_T_max  0.7942
_exptl_absorpt_correction_T_min  0.6098
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0171
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0147P)^2^+0.0440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0414
_refine_ls_wR_factor_ref         0.0417
_reflns_number_gt                2259
_reflns_number_total             2320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02387_si_002.cif
_cod_data_source_block           p21_b
_cod_original_sg_symbol_H-M      'P 21     '
_cod_database_code               4036515