Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization
Maria-Eleni Ragoussi; Stephen M. Walker; Andrea Piccanello; Benson M. Kariuki; Peter N. Horton; Neil Spencer; John S. Snaith; Journal of Organic Chemistry 75 (2010) 7347–7357; doi:10.1021/jo101631y

data_4025775
_publ_contact_author
;
B. Kariuki,
School of Chemistry,
Cardiff University,
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_contact_author_email       j.s.snaith@bham.ac.uk
_publ_section_title
;
 Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical
 Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7347
_journal_page_last               7357
_journal_paper_doi               10.1021/jo101631y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H39 N O4 S Si'
_chemical_formula_sum            'C24 H39 N O4 S Si'
_chemical_formula_weight         465.71
_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                66.224(17)
_cell_angle_beta                 81.948(19)
_cell_angle_gamma                80.06(4)
_cell_formula_units_Z            2
_cell_length_a                   10.751(4)
_cell_length_b                   11.432(4)
_cell_length_c                   11.761(6)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      65.64
_cell_measurement_theta_min      4.12
_cell_volume                     1299.0(10)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3914
_diffrn_reflns_theta_full        65.64
_diffrn_reflns_theta_max         65.64
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    1.773
_exptl_absorpt_correction_T_max  0.6184
_exptl_absorpt_correction_T_min  0.5026
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0569
_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^)+(0.1044P)^2^+0.6583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                1804
_reflns_number_total             3901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101631y_si_002.cif
_cod_data_source_block           mar1m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_original_cell_volume        1299.0(9)
_cod_database_code               4025775