Synthesis of Axially Chiral Amino Acid and Amino Alcohols via Additive-Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent Transformations of the Product Amidoaza[5]helicene
Takumi Furuta; Junya Yamamoto; Yuki Kitamura; Ayano Hashimoto; Hyuma Masu; Isao Azumaya; Toshiyuki Kan; Takeo Kawabata; Journal of Organic Chemistry 75 (2010) 7010–7013; doi:10.1021/jo101524t

data_4025734
_publ_section_title
;
 Synthesis of Axially Chiral Amino Acid and Amino Alcohols via
 Additive-Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent
 Transformations of the Product Amidoaza[5]helicene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7010
_journal_page_last               7013
_journal_paper_doi               10.1021/jo101524t
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C28 H19 N O2'
_chemical_formula_weight         401.44
_chemical_name_systematic
; 3-(4-Methoxyphenyl)dibenzo[a,k]phenanthridin-4(3H)-one
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.801(4)
_cell_angle_beta                 74.011(4)
_cell_angle_gamma                68.931(4)
_cell_formula_units_Z            2
_cell_length_a                   10.029(3)
_cell_length_b                   10.126(4)
_cell_length_c                   10.939(4)
_cell_measurement_reflns_used    633
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.48
_cell_measurement_theta_min      2.52
_cell_volume                     941.1(6)
_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      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0849
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4610
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[s^2^(Fo^2^)+(0.0644P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                2115
_reflns_number_total             3559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101524t_si_003.cif
_cod_data_source_block           a0902141mas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025734