organic compounds
In compound (II) (Fig. 2), aryl atom C56 in the molecule at
x, y, z) acts as hydrogen-bond donor to atom O4 in the
Compound (I)
(
Crystal data
molecule at (1 � x, 1 � y, 1 � z), so generating by inversion
� 3
C
M = 244.25
13
H
12
N
2
O
3
x
D = 1.441 Mg m
2
2
an R (14) ring analogous to that in compound (I), although
1
Mo Kꢃ radiation
Cell parameters from 2573
re¯ections
r
1 1
2 2
Monoclinic, P2 =n
now centred at ( , , ) (Fig. 6). At the same time, atom C54 at
1
2
Ê
a = 6.1293 (3) A
b = 13.9633 (8) A
(
1
x, y, z) acts as donor to atom O2 in the molecule at (x � 2,
ꢀ
Ê
ꢁ = 2.9±27.6
c = 13.2727 (8) AÊ
�
1
+ y, z), so generating by translation a C(11) chain running
ꢄ = 0.10 mm
T = 120 (2) K
Plate, colourless
ꢀ
ꢂ = 97.688 (4)
V = 1125.74 (11) A
Z = 4
parallel to the [210] direction. The combination of the two
hydrogen bonds then generates a [210] chain of centrosym-
Ê
3
0.34 Â 0.25 Â 0.09 mm
2
4
metric edge-fused R (14) and R (20) rings. Of the four mol-
4
2
4
Data collection
ecules which participate in the formation of an R (20) ring,
4
Bruker±Nonius KappaCCD area-
detector diffractometer
2573 independent re¯ections
1885 re¯ections with I > 2ꢅ(I)
two act as double donors and two as double acceptors of
hydrogen bonds (Fig. 7). Again, there are no direction-speci®c
interactions between adjacent chains.
The chain formation in compound (III) is rather different
from that in the isomeric compound, (II). In (III), aryl atoms
C53 and C55 in the molecule at (x, y, z) act as hydrogen-bond
donors to, respectively, atoms O6 and O4 in the molecules at
'
and ! scans
Absorption correction: multi-scan
SADABS; Sheldrick, 2003)
min = 0.954, Tmax = 0.991
2 444 measured re¯ections
Rint = 0.050
ꢀ
ꢁ
max = 27.6
(
T
h = � 7 ! 7
k = � 18 ! 16
l = � 17 ! 17
1
Re®nement
2
2
2
2
Re®nement on F
2
o
w = 1/[ꢅ (F ) + (0.1092P)
(
inversion a chain of edge-fused rings along [110] in which
1 � x, � y, 1 � z) and (� x, 1 � y, 1 � z), so generating by
2
R[F > 2ꢅ(F )] = 0.069
wR(F ) = 0.201, S = 1.05
2573 re¯ections
+ 0.6873P]
where P = (F
2
2
o
2
c
+ 2F
)/3
2
2
there are two distinct types of centrosymmetric R (16) ring
(Á/ꢅ)max < 0.001
Ê
� 3
� 3
165 parameters
H-atom parameters constrained
Áꢆmax = 0.47 e A
Áꢆmin = � 0.30 e AÊ
(Fig. 8), one involving O4 as the sole hydrogen-bond acceptor
and the other involving O6 only.
In contrast with the chain formation in compounds (I)±(III),
that in compound (IV) (Fig. 4) depends upon just one inter-
molecular CÐHÁ Á ÁO hydrogen bond. Atom C53 in the mol-
ecule at (x, y, z) acts as hydrogen-bond donor to atom O4 in
the molecule at (x, y, z � 1), thereby generating by translation
a simple C(8) chain running parallel to the [001] direction
Compound (II)
Crystal data
C
14
H N
14 2
O
4
Z = 2
� 3
M
r
= 274.27
Triclinic, P1
D
x
= 1.469 Mg m
Mo Kꢃ radiation
Cell parameters from 2847
re¯ections
ꢁ = 3.0±27.5
ꢄ = 0.11 mm
T = 120 (2) K
Block, colourless
0.52 Â 0.34 Â 0.16 mm
Ê
a = 5.6946 (2) A
Ê
b = 8.2994 (3) A
(
Fig. 9). Two such chains, antiparallel to one another, pass
Ê
ꢀ
c = 14.0411 (5) A
ꢃ = 73.5580 (17)
ꢀ
� 1
through each unit cell, but there are no direction-speci®c
interactions between adjacent chains.
ꢀ
ꢂ = 87.393 (2)
ꢇ = 77.037 (2)
V = 620.13 (4) A
ꢀ
In compound (V), there are no direction-speci®c inter-
molecular interactions. In particular, neither of the hydroxyl
groups participates in hydrogen-bond formation, because of
the steric shielding provided by the two adjacent tert-butyl
substituents. The nearest plausible donor/acceptor atoms to
O154 and O254 are, respectively, O154 at (1 � x, � y, 1 � z),
Ê
3
Data collection
Bruker±Nonius KappaCCD area-
detector diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2847 independent re¯ections
2331 re¯ections with I > 2ꢅ(I)
Rint = 0.034
ꢀ
ꢁmax = 27.5
i
i
h = � 7 ! 7
Ê
with OÁ Á ÁO and OÁ Á ÁH distances of 3.391 (2) and 3.56 A,
Tmin = 0.953, Tmax = 0.983
14 859 measured re¯ections
k = � 10 ! 10
l = � 18 ! 18
ii
respectively, and O254 at (2 � x, 1 � y, 1 � z), with OÁ Á ÁO
ii
Ê
and OÁ Á ÁH distances of 3.010 (2) and 2.91 A, respectively
Re®nement
[
symmetry codes: (i) 1 � x, � y, 1 � z; (ii) 2 � x, 1 � y,
2
2
2
2
Re®nement on F
2
o
w = 1/[ꢅ (F ) + (0.0732P)
+ 0.1975P]
where P = (F
1
� z].
2
R[F > 2ꢅ(F )] = 0.040
wR(F ) = 0.132, S = 1.11
2
2
2
c
o
+ 2F
)/3
2847 re¯ections
184 parameters
H-atom parameters constrained
(Á/ꢅ)max < 0.001
Ê
� 3
� 3
Experimental
Áꢆmax = 0.40 e A
Áꢆmin = � 0.40 e AÊ
0
For the preparation of compounds (I)±(V), mixtures of N,N -di-
methylbarbituric acid (0.50 g, 3.2 mmol) and the appropriate aryl-
aldehyde (3.2 mmol) in glacial acetic acid (4 ml) were heated under
re¯ux for 2 h, cooled and ®ltered. The resulting solids were washed
with diethyl ether (5 ml). Crystals suitable for single-crystal X-ray
diffraction were grown by slow evaporation of solutions in acetic acid
for (I) and (II), in acetonitrile for (III) and (IV), or in ethanol for (V).
For (I), m.p. 430±432 K (literature value 430±431 K; Suzuki et al.,
Compound (III)
Crystal data
C
14
H N
14 2
O
4
Z = 2
� 3
M
r
= 274.27
Triclinic, P1
D
x
= 1.454 Mg m
Mo Kꢃ radiation
a = 7.5906 (6) AÊ
Cell parameters from 2860
re¯ections
Ê
b = 8.2989 (7) A
Ê
c = 10.3010 (10) A
ꢀ
ꢁ = 3.1±27.5
1
976); for (II), m.p. 406±408 K; for (III), m.p. 416±418 K (literature
value 417±418 K; Suzuki et al., 1976); for (IV), m.p. 497±499 K
literature value 497±499 K; Rezende et al., 2001); for (V), m.p. 467±
69 K.
ꢀ
ꢀ
� 1
ꢃ = 92.544 (6)
ꢂ = 93.074 (5)
ꢇ = 104.456 (6)
V = 626.33 (10) A
ꢄ = 0.11 mm
T = 120 (2) K
(
ꢀ
Block, yellow
0.48 Â 0.44 Â 0.34 mm
Ê
3
4
ꢁ
Acta Cryst. (2005). C61, o306±o311
Rezende et al.
13 12
C H N
O , C14H
2 3 14
2 4
N O , C14
H N O
14 2 4
17 3
, C15H N O
3
and C21H N
28 2
O
4
o309