#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151364.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151364
loop_
_publ_author_name
'Malassene, Richard'
'Vanquelef, Enguerran'
'Toupet, Loic'
'Hurvois, Jean-Pierre'
'Moinet, Claude'
_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 &  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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.1167P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.97900(18) 0.52740(18) 0.18938(13) 0.0504(4) Uani 1 1 d . . .
N2 N 0.76888(19) 0.2495(2) 0.08631(13) 0.0572(5) Uani 1 1 d . . .
H1A H 0.6946 0.1796 0.0416 0.050 Uiso 1 1 d . . .
H1B H 0.8541 0.2911 0.0633 0.050 Uiso 1 1 d . . .
N3 N 0.4020(2) 0.0157(3) 0.10750(18) 0.0838(7) Uani 1 1 d . . .
C1 C 1.1419(2) 0.5506(2) 0.19518(16) 0.0549(6) Uani 1 1 d . . .
H1 H 1.1737 0.5946 0.1341 0.066 Uiso 1 1 calc R . .
C2 C 1.1643(3) 0.3987(3) 0.1759(2) 0.0739(7) Uani 1 1 d . . .
H2A H 1.1362 0.3531 0.0999 0.089 Uiso 1 1 calc R . .
H2B H 1.2719 0.4168 0.1957 0.089 Uiso 1 1 calc R . .
C3 C 1.0735(3) 0.2861(3) 0.23661(19) 0.0633(6) Uani 1 1 d . . .
H3 H 0.9994 0.2009 0.1832 0.076 Uiso 1 1 calc R . .
C4 C 0.9838(2) 0.3536(2) 0.30798(16) 0.0539(5) Uani 1 1 d . . .
H4A H 1.0547 0.4269 0.3683 0.065 Uiso 1 1 calc R . .
H4B H 0.9162 0.2737 0.3362 0.065 Uiso 1 1 calc R . .
C5 C 0.8875(2) 0.4318(2) 0.25539(14) 0.0449(5) Uani 1 1 d . . .
C6 C 0.7483(2) 0.3038(2) 0.18512(15) 0.0450(5) Uani 1 1 d . . .
C7 C 0.6187(2) 0.2471(2) 0.22547(16) 0.0539(5) Uani 1 1 d . . .
C8 C 0.5901(3) 0.3153(3) 0.33210(18) 0.0767(7) Uani 1 1 d . . .
H8A H 0.5163 0.3636 0.3202 0.092 Uiso 1 1 calc R . .
H8B H 0.5449 0.2346 0.3682 0.092 Uiso 1 1 calc R . .
C9 C 0.7280(3) 0.4280(3) 0.40361(19) 0.0801(8) Uani 1 1 d . . .
H9A H 0.7802 0.3753 0.4413 0.096 Uiso 1 1 calc R . .
H9B H 0.6970 0.4924 0.4566 0.096 Uiso 1 1 calc R . .
C10 C 0.8374(2) 0.5252(2) 0.34466(16) 0.0547(5) Uani 1 1 d . . .
H10A H 0.9269 0.5931 0.3952 0.066 Uiso 1 1 calc R . .
H10B H 0.7892 0.5865 0.3136 0.066 Uiso 1 1 calc R . .
C11 C 0.9249(3) 0.6311(2) 0.14971(15) 0.0530(5) Uani 1 1 d . . .
C12 C 1.0258(3) 0.7691(2) 0.13516(17) 0.0653(6) Uani 1 1 d . . .
H12 H 1.1305 0.7928 0.1521 0.078 Uiso 1 1 calc R . .
C13 C 0.9717(4) 0.8692(3) 0.0963(2) 0.0772(8) Uani 1 1 d . . .
H13 H 1.0407 0.9594 0.0868 0.093 Uiso 1 1 calc R . .
C14 C 0.8202(4) 0.8395(3) 0.0716(2) 0.0810(8) Uani 1 1 d . . .
H14 H 0.7855 0.9099 0.0472 0.097 Uiso 1 1 calc R . .
C15 C 0.7169(3) 0.7031(3) 0.08286(19) 0.0729(7) Uani 1 1 d . . .
H15 H 0.6126 0.6811 0.0648 0.087 Uiso 1 1 calc R . .
C16 C 0.7690(3) 0.6004(3) 0.12085(17) 0.0620(6) Uani 1 1 d . . .
H16 H 0.6990 0.5089 0.1274 0.074 Uiso 1 1 calc R . .
C17 C 1.2463(3) 0.6646(3) 0.29543(17) 0.0630(6) Uani 1 1 d . . .
H17A H 1.2070 0.7452 0.3151 0.076 Uiso 1 1 calc R . .
H17B H 1.2438 0.6138 0.3544 0.076 Uiso 1 1 calc R . .
C18 C 1.4109(3) 0.7329(3) 0.2786(2) 0.0785(8) Uani 1 1 d . . .
H18A H 1.4475 0.6516 0.2545 0.094 Uiso 1 1 calc R . .
H18B H 1.4134 0.7883 0.2222 0.094 Uiso 1 1 calc R . .
C19 C 1.5177(3) 0.8379(4) 0.3770(2) 0.0978(10) Uani 1 1 d . . .
H19A H 1.5158 0.7817 0.4329 0.117 Uiso 1 1 calc R . .
H19B H 1.4792 0.9177 0.4018 0.117 Uiso 1 1 calc R . .
C20 C 1.6816(3) 0.9100(4) 0.3625(3) 0.1099(11) Uani 1 1 d . . .
H20A H 1.7176 0.8305 0.3321 0.132 Uiso 1 1 calc R . .
H20B H 1.6847 0.9733 0.3112 0.132 Uiso 1 1 calc R . .
C21 C 1.7860(4) 1.0010(5) 0.4595(3) 0.1387(15) Uani 1 1 d . . .
H21A H 1.8865 1.0440 0.4427 0.166 Uiso 1 1 calc R . .
H21B H 1.7883 0.9385 0.5098 0.166 Uiso 1 1 calc R . .
H21C H 1.7523 1.0807 0.4903 0.166 Uiso 1 1 calc R . .
C22 C 1.1710(3) 0.2222(4) 0.3000(3) 0.0945(9) Uani 1 1 d . . .
H22A H 1.2266 0.1790 0.2532 0.113 Uiso 1 1 calc R . .
H22B H 1.1066 0.1454 0.3310 0.113 Uiso 1 1 calc R . .
H22C H 1.2416 0.3018 0.3559 0.113 Uiso 1 1 calc R . .
C23 C 0.4981(3) 0.1194(3) 0.16011(18) 0.0613(6) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C1 118.49(17) . . ?
C11 N1 C5 119.07(17) . . ?
C1 N1 C5 119.39(16) . . ?
C6 N2 H1A 120.6 . . ?
C6 N2 H1B 120.7 . . ?
H1A N2 H1B 118.3 . . ?
N1 C1 C2 110.17(18) . . ?
N1 C1 C17 115.16(18) . . ?
C2 C1 C17 113.3(2) . . ?
N1 C1 H1 105.8 . . ?
C2 C1 H1 105.8 . . ?
C17 C1 H1 105.8 . . ?
C3 C2 C1 115.2(2) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C22 110.6(2) . . ?
C4 C3 C2 111.35(19) . . ?
C22 C3 C2 113.2(2) . . ?
C4 C3 H3 107.1 . . ?
C22 C3 H3 107.1 . . ?
C2 C3 H3 107.1 . . ?
C3 C4 C5 116.10(17) . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
N1 C5 C6 110.79(15) . . ?
N1 C5 C10 111.93(16) . . ?
C6 C5 C10 110.62(16) . . ?
N1 C5 C4 109.26(16) . . ?
C6 C5 C4 105.88(16) . . ?
C10 C5 C4 108.16(16) . . ?
N2 C6 C7 123.99(18) . . ?
N2 C6 C5 115.55(17) . . ?
C7 C6 C5 120.34(17) . . ?
C6 C7 C23 117.99(19) . . ?
C6 C7 C8 124.17(19) . . ?
C23 C7 C8 117.74(19) . . ?
C9 C8 C7 114.6(2) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 113.1(2) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C5 112.63(18) . . ?
C9 C10 H10A 109.1 . . ?
C5 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C5 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 116.9(2) . . ?
C16 C11 N1 121.65(19) . . ?
C12 C11 N1 121.4(2) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C1 112.88(19) . . ?
C18 C17 H17A 109.0 . . ?
C1 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C1 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 114.2(2) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 115.5(3) . . ?
C18 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C18 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 115.1(3) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C7 179.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.408(3) . ?
N1 C1 1.467(3) . ?
N1 C5 1.480(2) . ?
N2 C6 1.342(3) . ?
N2 H1A 0.8641 . ?
N2 H1B 0.8733 . ?
N3 C23 1.148(3) . ?
C1 C2 1.524(4) . ?
C1 C17 1.541(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(3) . ?
C3 C22 1.516(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.538(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.536(3) . ?
C5 C10 1.537(3) . ?
C6 C7 1.352(3) . ?
C7 C23 1.425(3) . ?
C7 C8 1.500(3) . ?
C8 C9 1.481(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.396(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.520(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.505(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.510(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.450(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 -147.30(18) . . . . ?
C5 N1 C1 C2 52.6(2) . . . . ?
C11 N1 C1 C17 83.0(2) . . . . ?
C5 N1 C1 C17 -77.1(2) . . . . ?
N1 C1 C2 C3 -45.6(3) . . . . ?
C17 C1 C2 C3 85.0(2) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
C1 C2 C3 C22 -127.8(2) . . . . ?
C22 C3 C4 C5 176.22(19) . . . . ?
C2 C3 C4 C5 49.4(3) . . . . ?
C11 N1 C5 C6 75.4(2) . . . . ?
C1 N1 C5 C6 -124.67(18) . . . . ?
C11 N1 C5 C10 -48.6(2) . . . . ?
C1 N1 C5 C10 111.36(19) . . . . ?
C11 N1 C5 C4 -168.34(16) . . . . ?
C1 N1 C5 C4 -8.4(2) . . . . ?
C3 C4 C5 N1 -44.4(2) . . . . ?
C3 C4 C5 C6 75.0(2) . . . . ?
C3 C4 C5 C10 -166.41(17) . . . . ?
N1 C5 C6 N2 33.0(2) . . . . ?
C10 C5 C6 N2 157.76(17) . . . . ?
C4 C5 C6 N2 -85.3(2) . . . . ?
N1 C5 C6 C7 -150.61(19) . . . . ?
C10 C5 C6 C7 -25.9(3) . . . . ?
C4 C5 C6 C7 91.0(2) . . . . ?
N2 C6 C7 C23 1.6(3) . . . . ?
C5 C6 C7 C23 -174.37(18) . . . . ?
N2 C6 C7 C8 -174.6(2) . . . . ?
C5 C6 C7 C8 9.4(3) . . . . ?
C6 C7 C8 C9 -14.6(4) . . . . ?
C23 C7 C8 C9 169.1(2) . . . . ?
C7 C8 C9 C10 37.4(3) . . . . ?
C8 C9 C10 C5 -56.2(3) . . . . ?
N1 C5 C10 C9 172.72(19) . . . . ?
C6 C5 C10 C9 48.7(2) . . . . ?
C4 C5 C10 C9 -66.9(2) . . . . ?
C1 N1 C11 C16 166.43(19) . . . . ?
C5 N1 C11 C16 -33.4(3) . . . . ?
C1 N1 C11 C12 -12.1(3) . . . . ?
C5 N1 C11 C12 147.98(19) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
N1 C11 C12 C13 179.91(19) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
C12 C11 C16 C15 -1.9(3) . . . . ?
N1 C11 C16 C15 179.47(19) . . . . ?
N1 C1 C17 C18 -156.5(2) . . . . ?
C2 C1 C17 C18 75.3(3) . . . . ?
C1 C17 C18 C19 -176.6(2) . . . . ?
C17 C18 C19 C20 -179.0(3) . . . . ?
C18 C19 C20 C21 -175.2(3) . . . . ?
C6 C7 C23 N3 65(19) . . . . ?
C8 C7 C23 N3 -119(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101229736
