Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via a Tandem Aza Prins-Ritter/Friedel-Crafts Type Reaction of Endocyclic N-Acyliminium Ions
Kiran Indukuri; R. Unnava; Manash J. Deka; Anil K. Saikia; Journal of Organic Chemistry 78 (2013) 10629–10641; doi:10.1021/jo401450j

data_4028696
_publ_section_title
;
 Stereoselective Synthesis of Amido and Phenyl Azabicyclic Derivatives via
 a Tandem Aza Prins-Ritter/Friedel-Crafts Type Reaction of Endocyclic
 N-Acyliminium Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10629
_journal_page_last               10641
_journal_paper_doi               10.1021/jo401450j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C25 H23 N O2'
_chemical_formula_weight         369.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.064(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.493(2)
_cell_length_b                   19.484(4)
_cell_length_c                   11.334(2)
_cell_measurement_reflns_used    3212
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.25
_cell_measurement_theta_min      2.01
_cell_volume                     1963.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12969
_diffrn_reflns_theta_full        25.65
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.695
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.695
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                1960
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401450j_si_004.cif
_cod_data_source_block           ki2
_cod_original_sg_symbol_H-M      ' P 21/c'
_cod_database_code               4028696