organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Ê
0
�
.023 (1) A, respectively, in (II), and by � 0.110 (1) and
Ê
0.174 (1) A in (III). The bending of the heterocycle along
the lines O1Á Á ÁC4, C2Á Á ÁC6 and C3Á Á ÁC5 is 4.1 (1), 5.1 (1) and
ꢀ
ISSN 0108-2701
1.9 (1) , respectively, in (II), compared with 13.2 (1), 9.3 (1)
ꢀ
and 11.6 (1) in (III). The dihedral angle between the pseudo-
axial phenyl substituent and the ¯at part of the pyran ring is
ꢀ
ꢀ
5-Acetyl-2-amino-6-methyl-4-phenyl-
4H-pyran-3-carbonitrile and 2-amino-
5-benzoyl-6-methyl-4-phenyl-4H-
92.7 (1) in (II) and 93.2 (1) in (III).
pyran-3-carbonitrile acetonitrile
solvate
a
b
Vladimir N. Nesterov, * David J. Wiedenfeld, *
a
a
Svitlana V. Nesterova and Lucas F. Hastings
The C O group has interesting orientational preferences
relative to the C5 C6 double bond. In compound (II), the
groups are syn (`cisoid') [torsion angle C6ÐC5ÐC8ÐO2 =
a
Department of Natural Sciences, New Mexico Highlands University, Las Vegas,
b
NM 87701, USA, and Department of Chemistry, Marshall University, Huntington,
ꢀ
3
8.0 (2) ], while in (III) they are anti (`transoid') [torsion angle
ꢀ
WV 25755, USA
C6ÐC5ÐC8ÐO2 = � 141.4 (2) ]. In the ®rst case, a short
Ê
intramolecular contact (O2Á Á ÁH7A = 2.31 A) is present. In the
Received 26 October 2006
Accepted 13 November 2006
Online 30 November 2006
latter case, there is a short steric intramolecular contact
Ê
[
C7Á Á ÁC20 = 3.298 (2) A] which is shorter than the sum of the
van der Waals radii of two C atoms (Rowland & Taylor, 1996).
Probably, the CÁ Á ÁC contact plays a role in the orientation of
the bulky phenyl substituent in the molecule of (III) relative
The syntheses, X-ray structural investigations and calculations
of the conformational preferences of the carbonyl substituent
with respect to the pyran ring have been carried out for the
two title compounds, viz. C H N O , (II), and C H N -
to the heterocycle [torsion angle C5ÐC8ÐC9ÐC20 =
ꢀ
2
9.9 (2) ].
Similar to related compounds (Nesterov et al., 2004), both
1
5
14
2
2
20 16
2
O ÁC H N, (III), respectively. In both molecules, the hetero-
2
2
3
(
II) and (III) display a conjugation between the donor NH2
cyclic ring adopts a ¯attened boat conformation. In (II), the
carbonyl group and a double bond of the heterocyclic ring are
syn, but in (III) they are anti. The carbonyl group forms a short
contact with a methyl group H atom in (II). The dihedral
and the acceptor CN groups via the C2 C3 double bond. In
addition, the H atoms of the NH group participate in inter-
2
angles between the pseudo-axial phenyl substituent and the
ꢀ
¯at part of the pyran ring are 92.7 (1) and 93.2 (1) in (II) and
(
III), respectively. In the crystal structure of (II), inter-
molecular NÐHÁ Á ÁN and NÐHÁ Á ÁO hydrogen bonds link the
molecules into a sheet along the (103) plane, while in (III),
they link the molecules into ribbons along the a axis.
Comment
The present investigation of the title compounds, (II) and
(
III), is a continuation of our work that includes the syntheses
and structural studies of heterocyclic compounds, such as 4H-
pyran derivatives (Nesterov & Viltchinskaia, 2001; Nesterov et
al., 2004, 2005), that can be obtained starting from different
unsaturated nitriles (Nesterov et al., 2001a,b). Some 4H-pyran
derivatives are potential bioactive compounds, such as calcium
antagonists (Suarez et al., 2002) and potent apoptosis inducers
(
Kemnitzer et al., 2004; Zhang et al., 2005).
X-ray analysis shows that the molecules of (II) and (III)
have slightly different structures (Figs. 1 and 2). In both
molecules, the pyran ring adopts a ¯attened boat conforma-
tion: atoms O1 and C4 are displaced out of the C2/C3/C5/C6
Figure 1
A view of compound (II), showing the atom numbering used.
Displacement ellipsoids are drawn at the 50% probability level and H
atoms are shown as small spheres of arbitrary radii.
Ê
plane [planar to within 0.026 (1) and 0.021 (1) A in
compounds (II) and (III), respectively] by 0.060 (1) and
Acta Cryst. (2006). C62, o705±o708
DOI: 10.1107/S010827010604844X
# 2006 International Union of Crystallography o705