Diastereoselective preparation of 2,4,6-trisubstituted-2'-cyanopiperidines: application to the construction of the carbon framework of perhydrohistrionicotoxin
Malassene, Richard; Vanquelef, Enguerran; Toupet, Loic; Hurvois, Jean-Pierre; Moinet, Claude; Organic & Biomolecular Chemistry 1 (2003) 547–; doi:10.1039/b209387a

data_7151364
_publ_section_title
;
 Diastereoselective preparation of
 2,4,6-trisubstituted-2'-cyanopiperidines: application to the
 construction of the carbon framework of perhydrohistrionicotoxin
;
_journal_issue                   3
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              547
_journal_paper_doi               10.1039/b209387a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C23 H33 N3'
_chemical_formula_weight         351.52
_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                100.19(4)
_cell_angle_beta                 95.29(3)
_cell_angle_gamma                109.46(5)
_cell_formula_units_Z            2
_cell_length_a                   9.413(3)
_cell_length_b                   9.609(6)
_cell_length_c                   12.855(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1064.6(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4976
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.065
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.000(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.517
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1167P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2077
_reflns_number_gt                2601
_reflns_number_total             4625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209387a.txt
_cod_data_source_block           ev
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1064.6(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151364