Accessing 2-substituted piperidine iminosugars by organometallic addition/intramolecular reductive amination: aldehyde vs nitrone route
Mirabella, Stefania; Fibbi, Giulia; Matassini, Camilla; Faggi, Cristina; Goti, Andrea; Cardona, Francesca; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01848G

data_7155922
_publ_section_title
;
 Accessing 2-substituted piperidine iminosugars by organometallic
 addition/intramolecular reductive amination: aldehyde vs nitrone route
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01848G
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H17 N O3'
_chemical_formula_sum            'C9 H17 N O3'
_chemical_formula_weight         187.23
_chemical_name_systematic
(2S,3R,4S,5R)-3-hydroxy-4,5-O-(1-methylethylidene)-2-methyl-piperidine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date
;
'Tue Dec 13 14:03:15 2016'
;
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-04-20 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5000(2)
_cell_length_b                   9.8160(3)
_cell_length_c                   18.5860(6)
_cell_measurement_reflns_used    1516
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.649
_cell_measurement_theta_min      4.758
_cell_volume                     1003.42(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details
;
  1 omega  -70.00   23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   57.0000  -30.0000 93

  2 omega   73.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000  -30.0000 45

  3 omega   28.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -60.0000 49

  4 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  150.0000 45

  5 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  -30.0000 45

  6 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   30.0000 45

  7 omega   24.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -120.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2631
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.649
_diffrn_reflns_theta_min         4.758
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.87478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(1)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0372P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.445
_reflns_Friedel_fraction_full    0.633
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                1228
_reflns_number_total             1516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01848g2.cif
_cod_data_source_block           145
_cod_original_cell_volume        1003.4(2)
_cod_database_code               7155922
_shelxl_version_number           2014/6
_shelx_res_checksum              37916