Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D.
Reddy, P. Ganapati; Varghese, Babu; Baskaran, Sundarababu; Organic letters 5 (2003) 583–585; doi:10.1021/ol027563v

data_1507263
_publ_section_title
;
 Epoxide-initiated electrophilic cyclization of azides: a novel route for
 the stereoselective construction of azabicyclic ring systems and total
 synthesis of (+/-)-indolizidine 167B and 209D.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              583
_journal_page_last               585
_journal_paper_doi               10.1021/ol027563v
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C16 H21 Br Cl N O2'
_chemical_formula_weight         374.70
_chemical_name_systematic
;
 ?
;
_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                 97.29(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.517(7)
_cell_length_b                   7.363(10)
_cell_length_c                   18.932(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1592(3)
_computing_cell_refinement       'cad4 programs'
_computing_data_collection       'cad4 programs'
_computing_data_reduction        'XCAD4 (WINGX)'
_computing_molecular_graphics    'ORTEP3 (WINGX)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-96 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'cad4 diffractometer'
_diffrn_measurement_method       'omega twotheta'
_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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.1418
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2952
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '1 hour'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.753
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   1
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                1291
_reflns_number_total             2804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol027563vsi20021227_091604.cif
_cod_data_source_block           greddy
_cod_original_cell_volume        1592(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1507263
_exptl_absorpt_factor_mur        0.000