Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control.
O'Brien, Matthew; Leach, Andrew; Armstrong, Roly J.; Chong, Keting; Sheridan, Ross; Organic & biomolecular chemistry 10 (2012) 2392–2394; doi:10.1039/c2ob07008a

data_7152265
_publ_section_title
;
 Furanyl cyclic amines: a diastereoselective synthesis of
 2,6-syn-disubstituted piperidines under thermodynamic control.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2392
_journal_page_last               2394
_journal_paper_doi               10.1039/c2ob07008a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C17 H21 N O3 S'
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41
_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                 109.528(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.0051(4)
_cell_length_b                   11.4052(2)
_cell_length_c                   15.9100(3)
_cell_measurement_reflns_used    35045
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     3250.23(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37289
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+1.7268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                5036
_reflns_number_total             7717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob07008a.txt
_cod_data_source_block           sl0972
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152265