Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids
Wen-Hua Chiou; Gau-Hong Lin; Chih-Wei Liang; Journal of Organic Chemistry 75 (2010) 1748–1751; doi:10.1021/jo902324h

data_4025258
_publ_section_title
;
 Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and
 3-Hydroxypipecolic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1748
_journal_page_last               1751
_journal_paper_doi               10.1021/jo902324h
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C11 H21 N O4'
_chemical_formula_sum            'C11 H21 N O4'
_chemical_formula_weight         231.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.068(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7989(5)
_cell_length_b                   12.0265(10)
_cell_length_c                   9.0540(8)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.0822
_cell_measurement_theta_min      2.8905
_cell_volume                     603.62(9)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7989
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) 
(compiled Feb 27 2009,15:38:38) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallepied
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0630
_reflns_number_gt                1957
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902324h_si_002.cif
_cod_data_source_block           swdebn
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025258