A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines.
Ebule, Rene; Mudshinge, Sagar; Nantz, Michael H.; Mashuta, Mark S.; Hammond, Gerald B.; Xu, Bo; The Journal of organic chemistry 84 (2019) 3249–3259; doi:10.1021/acs.joc.8b03162

data_4033928
_publ_section_title
;
 A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of
 4-Chloropiperidines from Homoallylic Amines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3249
_journal_page_last               3259
_journal_paper_doi               10.1021/acs.joc.8b03162
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C11 H13 Cl N2 O2'
_chemical_formula_sum            'C11 H13 Cl N2 O2'
_chemical_formula_weight         240.68
_chemical_name_common
; 
 1-(4-nitrophenyl)-4-chloro-piperidine
;
_chemical_name_systematic
; 
 1-(4-nitrophenyl)-4-chloro-piperidine
;
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.33.66 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2486(2)
_cell_length_b                   10.17867(17)
_cell_length_c                   6.17147(11)
_cell_measurement_reflns_used    12554
_cell_measurement_temperature    101.95(10)
_cell_measurement_theta_max      33.7450
_cell_measurement_theta_min      3.8430
_cell_volume                     1083.51(3)
_computing_cell_refinement       '<i>CrysAlis PRO</i> (Agilent, 2010)'
_computing_data_collection       '<i>CrysAlis PRO</i> (Agilent, 2010)'
_computing_data_reduction        '<i>CrysAlis PRO</i> (Agilent, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae<i>et al.</i>, 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  '<i>SHELXL</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      101.95(10)
_diffrn_detector_area_resol_mean 10.2836
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -82.00  -56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759  -57.0000   30.0000 26

  2 omega  -97.00  -55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759  -57.0000  150.0000 42

  3 omega   -8.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   77.0000 -150.0000 103

  4 omega  -54.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446  -77.0000  150.0000 111

  5 omega   65.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   57.0000  -90.0000 25

  6 omega   -5.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   57.0000  120.0000 92

  7 omega  -52.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759   57.0000  -60.0000 103

  8 omega  -52.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.7759   57.0000   60.0000 103

  9 omega  -10.00  102.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446   77.0000    0.0000 112

 10 omega  -55.00   14.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2446  -77.0000  -90.0000 69

;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26127
_diffrn_reflns_theta_full        33.12
_diffrn_reflns_theta_max         33.12
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0214P)^2^+0.5871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                1941
_reflns_number_total             2160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b03162_si_002.cif
_cod_data_source_block           2n
_cod_original_sg_symbol_Hall     '-P 2ac 2n  '
_cod_database_code               4033928
_exptl_absorpt_correction_details
;
(CrysAlisPro SCALE3 ABSPACK, Oxford Diffraction Ltd., 2010) 
;