Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar Cycloaddition of 2-Acyl-5-aminooxazolium Salts
Corey H. Basch; Jameson A. Brinck; Joaquin E. Ramos; Stephen A. Habay; Glenn P.A. Yap; Journal of Organic Chemistry 77 (2012) 10416–10421; doi:10.1021/jo301600p

data_4027693
_publ_section_title
;
 Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar
 Cycloaddition of 2-Acyl-5-aminooxazolium Salts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10416
_journal_page_last               10421
_journal_paper_doi               10.1021/jo301600p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H29 B Cl2 F4 N2 O2'
_chemical_formula_weight         439.12
_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                78.489(4)
_cell_angle_beta                 87.071(4)
_cell_angle_gamma                82.042(4)
_cell_formula_units_Z            2
_cell_length_a                   8.654(2)
_cell_length_b                   9.693(2)
_cell_length_c                   12.619(3)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.38
_cell_volume                     1026.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13980
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5075
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0844
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1121P)^2^+1.2238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2521
_reflns_number_gt                3036
_reflns_number_total             5075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301600p_si_002.cif
_cod_data_source_block           step001
_cod_database_code               4027693