#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/08/4020896.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_4020896
loop_
_publ_author_name
'Robert A. Stockman'
'Alex Sinclair'
'Louise G. Arini'
'Peter Szeto'
'David L. Hughes'
_publ_section_title
;
 A Two-Directional Synthesis of (+-)-Perhydrohistrionicotoxin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1598
_journal_page_last               1602
_journal_paper_doi               10.1021/jo035639a
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C13 H17 N3 O'
_chemical_formula_structural     'dinitrile histrionicotoxin derivative, II'
_chemical_formula_sum            'C13 H17 N3 O'
_chemical_formula_weight         231.30
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   28.183(6)
_cell_length_b                   9.3620(19)
_cell_length_c                   18.789(4)
_cell_measurement_temperature    140(1)
_cell_volume                     4903.7(17)
_diffrn_ambient_temperature      140(1)
_exptl_crystal_density_diffrn    1.253
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4020896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.40169(8) 0.4748(2) 0.58553(12) 0.0329(5) Uani 1 1 d . . .
N2 N 0.36444(6) 0.51748(18) 0.52506(10) 0.0282(4) Uani 1 1 d . . .
O3 O 0.37423(5) 0.66956(15) 0.51820(8) 0.0318(4) Uani 1 1 d . . .
C4 C 0.38403(8) 0.7268(2) 0.59160(12) 0.0334(5) Uani 1 1 d . . .
H4 H 0.3539 0.7587 0.6066 0.040 Uiso 1 1 calc R . .
C5 C 0.40489(9) 0.6014(2) 0.64028(13) 0.0374(6) Uani 1 1 d . . .
H5 H 0.3856 0.5828 0.6786 0.045 Uiso 1 1 calc R . .
C6 C 0.45790(10) 0.6114(3) 0.66985(17) 0.0600(8) Uani 1 1 d . . .
H6A H 0.4665 0.5427 0.7082 0.072 Uiso 1 1 calc R . .
H6B H 0.4661 0.7065 0.6882 0.072 Uiso 1 1 calc R . .
C7 C 0.48350(10) 0.5773(3) 0.6050(2) 0.0726(10) Uani 1 1 d . . .
H7A H 0.4875 0.6632 0.5776 0.087 Uiso 1 1 calc R . .
H7B H 0.5148 0.5359 0.6207 0.087 Uiso 1 1 calc R . .
C8 C 0.45160(9) 0.4720(3) 0.56012(16) 0.0473(7) Uani 1 1 d . . .
H8A H 0.4652 0.3768 0.5660 0.057 Uiso 1 1 calc R . .
H8B H 0.4486 0.4978 0.5097 0.057 Uiso 1 1 calc R . .
C9 C 0.39051(8) 0.3280(2) 0.61574(13) 0.0378(6) Uani 1 1 d . . .
H9A H 0.3980 0.2547 0.5826 0.045 Uiso 1 1 calc R . .
H9B H 0.4114 0.3133 0.6610 0.045 Uiso 1 1 calc R . .
C10 C 0.33885(9) 0.3092(3) 0.62823(13) 0.0399(6) Uani 1 1 d . . .
H10A H 0.3334 0.2107 0.6408 0.048 Uiso 1 1 calc R . .
H10B H 0.3325 0.3695 0.6678 0.048 Uiso 1 1 calc R . .
C11 C 0.30543(8) 0.3494(2) 0.56039(12) 0.0335(5) Uani 1 1 d . . .
H11A H 0.2724 0.3385 0.5682 0.040 Uiso 1 1 calc R . .
H11B H 0.3109 0.2866 0.5213 0.040 Uiso 1 1 calc R . .
C12 C 0.31460(8) 0.5044(2) 0.54045(12) 0.0283(5) Uani 1 1 d . . .
H12 H 0.3103 0.5669 0.5808 0.034 Uiso 1 1 calc R . .
C13 C 0.28165(8) 0.5542(2) 0.47269(12) 0.0322(5) Uani 1 1 d . . .
H13A H 0.2897 0.6516 0.4617 0.039 Uiso 1 1 calc R . .
H13B H 0.2869 0.4945 0.4324 0.039 Uiso 1 1 calc R . .
C14 C 0.23094(9) 0.5474(2) 0.48181(12) 0.0342(5) Uani 1 1 d . . .
N15 N 0.19171(8) 0.5409(2) 0.49169(12) 0.0478(6) Uani 1 1 d . . .
C16 C 0.41598(9) 0.8508(3) 0.58882(13) 0.0384(6) Uani 1 1 d . . .
N17 N 0.44003(9) 0.9487(2) 0.58768(12) 0.0532(6) Uani 1 1 d . . .
C21 C 0.09739(8) 0.5130(2) 0.16424(12) 0.0310(5) Uani 1 1 d . . .
N22 N 0.14501(6) 0.51297(17) 0.21030(10) 0.0292(4) Uani 1 1 d . . .
O23 O 0.15486(6) 0.36050(15) 0.21942(8) 0.0347(4) Uani 1 1 d . . .
C24 C 0.13989(8) 0.2941(2) 0.14930(12) 0.0323(5) Uani 1 1 d . . .
H24 H 0.1669 0.2932 0.1219 0.039 Uiso 1 1 calc R . .
C25 C 0.09908(8) 0.3877(2) 0.10965(12) 0.0299(5) Uani 1 1 d . . .
H25 H 0.1070 0.4224 0.0636 0.036 Uiso 1 1 calc R . .
C26 C 0.04892(8) 0.3226(2) 0.10082(13) 0.0365(6) Uani 1 1 d . . .
H26A H 0.0495 0.2242 0.0848 0.044 Uiso 1 1 calc R . .
H26B H 0.0269 0.3764 0.0663 0.044 Uiso 1 1 calc R . .
C27 C 0.03415(9) 0.3312(3) 0.17625(13) 0.0408(6) Uani 1 1 d . . .
H27A H -0.0005 0.3359 0.1733 0.049 Uiso 1 1 calc R . .
H27B H 0.0458 0.2488 0.2049 0.049 Uiso 1 1 calc R . .
C28 C 0.05754(9) 0.4687(3) 0.20882(14) 0.0425(6) Uani 1 1 d . . .
H28A H 0.0713 0.4527 0.2586 0.051 Uiso 1 1 calc R . .
H28B H 0.0337 0.5439 0.2074 0.051 Uiso 1 1 calc R . .
C29 C 0.08647(9) 0.6590(2) 0.12901(13) 0.0385(6) Uani 1 1 d . . .
H29A H 0.0581 0.6507 0.0932 0.046 Uiso 1 1 calc R . .
H29B H 0.0792 0.7259 0.1654 0.046 Uiso 1 1 calc R . .
C30 C 0.12706(9) 0.7194(3) 0.09339(13) 0.0416(6) Uani 1 1 d . . .
H30A H 0.1320 0.6603 0.0527 0.050 Uiso 1 1 calc R . .
H30B H 0.1190 0.8151 0.0759 0.050 Uiso 1 1 calc R . .
C31 C 0.17241(9) 0.7229(2) 0.14792(13) 0.0390(6) Uani 1 1 d . . .
H31A H 0.1677 0.7848 0.1877 0.047 Uiso 1 1 calc R . .
H31B H 0.1986 0.7612 0.1256 0.047 Uiso 1 1 calc R . .
C32 C 0.18516(8) 0.5725(2) 0.17616(12) 0.0319(5) Uani 1 1 d . . .
H32 H 0.1901 0.5113 0.1355 0.038 Uiso 1 1 calc R . .
C33 C 0.23061(8) 0.5680(3) 0.23225(14) 0.0398(6) Uani 1 1 d . . .
H33A H 0.2347 0.4721 0.2517 0.048 Uiso 1 1 calc R . .
H33B H 0.2582 0.5893 0.2086 0.048 Uiso 1 1 calc R . .
C34 C 0.22958(8) 0.6688(2) 0.29169(13) 0.0339(5) Uani 1 1 d . . .
N35 N 0.22911(7) 0.7499(2) 0.33736(12) 0.0456(5) Uani 1 1 d . . .
C36 C 0.12708(9) 0.1452(3) 0.16562(13) 0.0380(6) Uani 1 1 d . . .
N37 N 0.11805(9) 0.0311(2) 0.18082(13) 0.0551(6) Uani 1 1 d . . .
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
C1 N2 1.484(3) . ?
C1 C9 1.537(3) . ?
C1 C8 1.550(3) . ?
C1 C5 1.564(3) . ?
N2 O3 1.460(2) . ?
N2 C12 1.480(3) . ?
O3 C4 1.468(3) . ?
C4 C16 1.475(3) . ?
C4 C5 1.550(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.519(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.539(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.506(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.530(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.534(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.465(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N15 1.149(3) . ?
C16 N17 1.142(3) . ?
C21 N22 1.486(3) . ?
C21 C29 1.530(3) . ?
C21 C28 1.553(3) . ?
C21 C25 1.563(3) . ?
N22 O23 1.459(2) . ?
N22 C32 1.488(3) . ?
O23 C24 1.462(3) . ?
C24 C36 1.483(3) . ?
C24 C25 1.548(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.526(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.537(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.532(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.517(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.516(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.529(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.535(3) . ?
C32 H32 0.9800 . ?
C33 C34 1.465(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N35 1.148(3) . ?
C36 N37 1.145(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327505
