Radical-mediated nitrile translocation as the key step in the stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates.
Vervisch, Karel; D'hooghe, Matthias; Törnroos, Karl W; De Kimpe, Norbert; Organic & biomolecular chemistry 10 (2012) 3308–3314; doi:10.1039/c2ob07062f

data_7152284
_publ_section_title
;
 Radical-mediated nitrile translocation as the key step in the
 stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to
 methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3308
_journal_page_last               3314
_journal_paper_doi               10.1039/c2ob07062f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.40
_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                74.9440(10)
_cell_angle_beta                 84.1930(10)
_cell_angle_gamma                77.5330(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7575(3)
_cell_length_b                   10.4335(5)
_cell_length_c                   14.3548(7)
_cell_measurement_reflns_used    6774
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.215
_cell_volume                     812.14(7)
_computing_cell_refinement
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_data_collection
;
Bruker (2008). APEX2, version 2008.5-0, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_data_reduction
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_molecular_graphics
;
Brandenburg, K. (2009). DIAMOND. Version 3.2c. Crystal Impact GbR, Bonn,
Germany.
;
_computing_publication_material
;
Bruker AXS (2008). SHELXTL. Version 2008/1. Bruker AXS Inc., Madison,
Wisconsin, USA.
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_computing_structure_solution
;
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker TXS Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12358
_diffrn_reflns_theta_full        28.77
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS version 2008/1, G.M Sheldrick, University of
G\"ttingen, Germany, 2008.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0642P)^2^+0.2362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                3688
_reflns_number_total             4224
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ob07062f.txt
_cod_data_source_block           kv234
_cod_database_code               7152284