Synthesis of Stereodefined Piperidines from Aziridines and Their Transformation into Conformationally Constrained Amino Acids, Amino Alcohols and 2,7-Diazabicyclo[3.3.1]nonanes
Karel Vervisch; Matthias D'hooghe; Karl W. Törnroos; Norbert De Kimpe; Journal of Organic Chemistry 75 (2010) 7734–7744; doi:10.1021/jo101646u

data_4025829
_publ_section_title
;
 Synthesis of Stereodefined Piperidines from Aziridines and Their
 Transformation into Conformationally Constrained Amino Acids, Amino
 Alcohols and 2,7-Diazabicyclo[3.3.1]nonanes
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7734
_journal_page_last               7744
_journal_paper_doi               10.1021/jo101646u
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H23 Cl N2'
_chemical_formula_sum            'C21 H23 Cl N2'
_chemical_formula_weight         338.86
_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                 92.3122(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3116(3)
_cell_length_b                   8.7530(2)
_cell_length_c                   17.0047(4)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.40
_cell_volume                     1830.99(7)
_computing_cell_refinement       'Bruker SAINT v. 7.56A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT v. 7.56A'
_computing_molecular_graphics    'Bruker SHELXTL version 2008/4'
_computing_publication_material  'Bruker SHELXTL version 2008/4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean '24 \um'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30645
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.95355
_exptl_absorpt_correction_T_min  0.91012
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;  
Bruker AXS (2003). SHELXTL. Version 6.14. 
Bruker AXS Inc., Madison, Wisconsin, USA.  
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pinacoid
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0572P)^2^+0.5173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                5333
_reflns_number_total             5650
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo101646u_si_002.cif
_cod_data_source_block           Compound11b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025829