Four 7-ar-yl-substituted pyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones: Similar mol-ecular structures but different crystal structures

Article abstract of DOI:10.1107/S0108270109005514

Mol-ecules of 1,3-dimethyl-7-(4-methyl-phen-yl)pyrido[2,3-d]pyrimidine-2, 4(1H,3H)-dione, C16H15N3O2, (I), are linked by paired C - H...O hydrogen bonds to form centrosymmetric R 2 ²(10) dimers, which are linked into chains by a single π-π stac

Full text of DOI:10.1107/S0108270109005514

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
prepared by cyclocondensation reactions between 6-amino-
pyrimidine-5-carbaldehydes and acetophenones, utilizing sol-
vent-free fusion reactions promoted by BF3–Et2O catalysis.
ISSN 0108-2701
Four 7-aryl-substituted pyrido[2,3-d]-
pyrimidine-2,4(1H,3H)-diones: similar
molecular structures but different
crystal structures
Jorge Trilleras,a Jairo Quiroga,a Justo Cobo,b Michael B.
Hursthousec and Christopher Glidewelld*
a
´
´
´
Grupo de Investigacion de Compuestos Heterocıclicos, Departamento de Quımica,
b
´
Universidad de Valle, AA 25360 Cali, Colombia, Departamento de Quımica
Inorganica y Organica, Universidad de Jaen, 23071 Jaen, Spain, cSchool of
Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England,
and dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
´
´
´
´
Received 3 February 2009
Accepted 16 February 2009
Online 21 February 2009
Molecules of 1,3-dimethyl-7-(4-methylphenyl)pyrido[2,3-d]-
pyrimidine-2,4(1H,3H)-dione, C16H15N3O2, (I), are linked by
paired C—Hꢀ ꢀ ꢀO hydrogen bonds to form centrosymmetric
R22(10) dimers, which are linked into chains by a single
ꢀ–ꢀ stacking interaction. A single C—Hꢀ ꢀ ꢀO hydrogen bond
links the molecules of 7-(biphenyl-4-yl)-1,3-dimethylpyrido-
[2,3-d]pyrimidine-2,4(1H,3H)-dione, C21H17N3O2, (II), into
C(10) chains, which are weakly linked into sheets by a ꢀ–ꢀ
stacking interaction. In 7-(4-fluorophenyl)-3-methylpyrido-
[2,3-d]pyrimidine-2,4(1H,3H)-dione, C14H10FN3O2, (III), an
N—Hꢀ ꢀ ꢀO hydrogen bond links the molecules into C(6)
chains, which are linked into sheets by a ꢀ–ꢀ stacking
interaction. The molecules of 7-(4-methoxyphenyl)-3-methyl-
pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, C15H13N3O3, (IV),
are also linked into C(6) chains by an N—Hꢀ ꢀ ꢀO hydrogen
bond, but here the chains are linked into sheets by a
combination of two independent C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen
bonds.
While the molecular structures of the pair of compounds
1,3-dimethyl-7-(4-methylphenyl)pyrido[2,3-d]pyrimidine-2,4-
(1H,3H)-dione, (I) (Fig. 1), and 7-(1,10-biphenyl-4-yl)-1,3-di-
methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, (II) (Fig. 2),
are broadly similar in constitution and very similar in
conformation, they exhibit significant differences in their
crystal structures, in particular in their space groups and in
their pattern of supramolecular aggregation. Similarly, the pair
of compounds 7-(4-fluorophenyl)-3-methylpyrido[2,3-d]pyri-
midine-2,4(1H,3H)-dione, (III) (Fig. 3), and 7-(4-methoxy
phenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione,
(IV) (Fig. 4), which are closely related to (I) and (II), have
Comment
Pyrido[2,3-d]pyrimidine heterocycles (also known as 5-de-
azapteridines) have received considerable attention over the
past decade as a result of the wide range of biological activity
that they exhibit (Devi et al., 2003; Tu et al., 2008), including,
for example, bronchodilator, vasodilator, antiallergic, cardio-
tonic, antihypertensive or hepatoprotective activities, as well
as for their role in the treatment of proliferative diseases
(Devi et al., 2004). As part of a wide-ranging project on the
synthesis and characterization of fused pyrimidine systems
under solvent-free conditions, we report here the structures
of four examples of 7-arylpyrido[2,3-d]pyrimidine derivatives
Figure 1
The molecular structure of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
o134 # 2009 International Union of Crystallography
doi:10.1107/S0108270109005514
Acta Cryst. (2009). C65, o134–o139

organic compounds
similar constitutions and conformations, but again they crys-
tallize in different space groups and exhibit different patterns
of supramolecular aggregation. Overall, no two of the
compounds reported here crystallize in the same space group
or have similar unit-cell dimensions or exhibit the same
pattern of direction-specific intermolecular interactions.
The molecular conformations are straightforwardly defin-
able in terms of the interplanar angle between the pyridine
ring and the pendent aryl ring (C71–C76), with an additional
angle between the two rings of the biphenyl-4-yl substituent in
(II) (Table 1). These angles indicate that the molecular
skeletons do not deviate much from overall planarity, a point
˚
emphasized by the very small deviation, 0.012 (5) A, of the
methoxy C atom from the plane of the adjacent aryl ring in
(IV). The bond distances and angles show no unexpected
values.
In our analysis of the intermolecular interactions, we have
discounted all intermolecular contacts involving methyl C—H
bonds on the usual grounds that these bonds are of low acidity,
while the rotation about the adjacent C—C bonds of methyl
groups bonded to planar rings are hindered by extremely low
barriers, typically a few J molꢁ1 (Tannenbaum et al., 1956;
Naylor & Wilson, 1957), and so are likely to be undergoing
very fast rotation about the adjacent C—C bonds.
In (I), there is a single C—Hꢀ ꢀ ꢀO hydrogen bond utilizing a
pyridine C—H bond as the donor (Table 2), and this links
pairs of molecules into centrosymmetric dimers characterized
by an R22(10) (Bernstein et al., 1995) motif. In addition, the
pyridine rings of the molecules at (x, y, z) and (ꢁx, ꢁy + 1,
ꢁz + 1) are strictly parallel, with an interplanar spacing
Figure 2
The molecular structure of (II), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
˚
of 3.439 (2) A; the corresponding ring-centroid separation is
˚
˚
3.693 (2) A, with a near-ideal ring-centroid offset of 1.345 (2) A.
The combined effect of these two interactions is to link the
molecules into a ꢀ-stacked chain of hydrogen-bonded dimers,
running parallel to the [010] direction, with R22(10) rings
centred at (0, n, 12 ), where n represents an integer, alternating
1
1
with ꢀ–ꢀ stacking interactions across (0, n + , ), where n
again represents an integer (Fig. 5).
2
2
The crystal structure of (II) also contains just one inter-
molecular C—Hꢀ ꢀ ꢀO hydrogen bond, but this now involves an
aryl C—H bond as the donor (Table 2), and its effect is to link
3
molecules related by the 21 screw axis along (12, y, ) into a
4
Figure 3
The molecular structure of (III), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
Figure 5
A stereoview of part of the crystal structure of (I), showing the formation
of a chain of ꢀ-stacked hydrogen-bonded dimers along [010]. For the sake
of clarity, H atoms not involved in the motif shown have been omitted.
Figure 4
The molecular structure of (IV), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
ꢂ
Acta Cryst. (2009). C65, o134–o139
Trilleras et al.
C16H15N3O2, C21H17N3O2, C14H10FN3O2 and C15H13N3O3 o135

organic compounds
C(10) chain running parallel to the [010] direction. The pyri-
dine and phenyl rings in the molecules at (x, y, z) and (ꢁx,
ꢁy + 1, ꢁz + 1), respectively, are not parallel, but the dihedral
angle between them is only 12.8 (2)ꢃ; the ring-centroid
(IV) consists of molecules related by translation along [100].
In addition, the subsequent linking of the chains is different in
the two structures. The pyridine ring in the molecule of (III) at
(x, y, z) makes angles of 1.1 (2)ꢃ with the phenyl ring in each of
1
1
1
1
˚
separation is 3.718 (2) A and the interplanar distance is ca
the molecules at (x + , ꢁy + , ꢁz + 1) and (x ꢁ , ꢁy + ,
2
2
2
2
˚
˚
3.53 A, corresponding to a ring-centroid offset of ca 1.17 A.
Thus, these centrosymmetrically related molecules are weakly
linked by the ꢀ–ꢀ stacking interaction and the overall effect of
this is to link the hydrogen-bonded chain into a sheet parallel
to (102) (Fig. 6).
ꢁz + 1), with ring-centroid separations of 3.759 (2) and
˚
3.748 (2) A, respectively. The interplanar spacings are ca 3.315
˚
and ca 3.39 A, respectively, corresponding to ring-centroid
˚
offsets of ca 1.77 and ca 1.60 A, respectively. The co-operative
action of these two independent stacking interactions along
[100] links the hydrogen-bonded chains along [010] into a
sheet parallel to (001) (Fig. 7). In the structure of (IV), by
contrast, the chains generated by the C—Hꢀ ꢀ ꢀO hydrogen
bond are linked by two independent C—Hꢀ ꢀ ꢀꢀ(arene)
hydrogen bonds, both involving the same ring as the acceptor.
The C71–C76 ring in the molecule at (x, y, z) acts as a
hydrogen-bond acceptor from atom C72 in the molecule at
In each of (III) and (IV), a single N—Hꢀ ꢀ ꢀO hydrogen-
bond links the molecules into a C(6) chain. Although the same
hydrogen-bond donor and acceptor are utilized in each
structure, the construction and orientation of the chains is
different. In (III), the chain consists of molecules related by a
21 screw axis parallel to the [010] direction, while the chain in
1
2
1
2
(x + , ꢁy, z) and from atom C75 in the molecule at (x ꢁ ,
ꢁy + 1, z), so forming a chain running parallel to the [110]
direction; the two C—Hꢀ ꢀ ꢀꢀ hydrogen bonds lie on opposite
faces of the ring, with Cꢀ ꢀ ꢀCgꢀ ꢀ ꢀC and Hꢀ ꢀ ꢀCgꢀ ꢀ ꢀH angles of
179 and 177ꢃ, respectively. The combination of the [100] and
[110] chains then generates a sheet parallel to (001) (Fig. 8).
In view of the different patterns of supramolecular aggre-
gation found here for (I)–(IV), it is of interest briefly to
compare these structures with those of the closely related
compounds (V) [Cambridge Structural Database (Allen,
2002) refcode QOQQIW (Sarkhel et al., 2001)] and (VI)
(refcode XEBCUD; Wang et al., 2006). The crystal structure of
(V) was described (Sarkhel et al., 2001) as containing C—
Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀBr hydrogen bonds and ꢀ–ꢀ stacking
interactions, although the structural effects of these inter-
actions were not specified. However, it is now well established
that Br and Cl bonded to carbon are both exceptionally poor
acceptors of hydrogen bonds, even from O—H and N—H
units, so that the C—Hꢀ ꢀ ꢀBr contacts in (V) and the C—
Hꢀ ꢀ ꢀCl contacts in (VI) are likely to be no more than normal
van der Waals contacts (Brammer et al., 2001; Thallypally &
Figure 6
A stereoview of part of the crystal structure of (II), showing the
formation of a sheet parallel to (102) built from ꢀ-stacked hydrogen-
bonded chains along [010]. For the sake of clarity, H atoms not involved in
the motif shown have been omitted.
Figure 7
Figure 8
A stereoview of part of the crystal structure of (III), showing the
formation of a sheet parallel to (001) built from ꢀ-stacked hydrogen-
bonded chains along [010]. For the sake of clarity, H atoms not involved in
the motif shown have been omitted.
A stereoview of part of the crystal structure of (IV), showing the
formation of a sheet parallel to (001) built from one C—Hꢀ ꢀ ꢀO hydrogen
bond and two C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds. For the sake of clarity,
H atoms not involved in the motif shown have been omitted.
ꢂ
o136 Trilleras et al. C16H15N3O2, C21H17N3O2, C14H10FN3O2 and C15H13N3O3
Acta Cryst. (2009). C65, o134–o139

organic compounds
Nangia, 2001). Accordingly, the structure of (V) consists of
C(10) hydrogen-bonded chains, running parallel to the [001]
direction and built from a single C—Hꢀ ꢀ ꢀO hydrogen bond;
antiparallel pairs of these chains, related by inversion, are
linked by the ꢀ–ꢀ stacking interaction (Fig. 9). The original
report on (VI) (Wang et al., 2006) stated that ‘the crystal
structure is stabilized by N—Hꢀ ꢀ ꢀO, C—Hꢀ ꢀ ꢀO and C—
Hꢀ ꢀ ꢀCl hydrogen bonds’, but it gave no information as to the
actions of these interactions. Re-examination of this structure
shows that most of the so-called hydrogen bonds listed by the
authors have Hꢀ ꢀ ꢀA distances far too long to be of structural
significance. In the event, only two hydrogen bonds linking the
heterocyclic components are significant, and they link these
molecules into chains of centrosymmetric rings running
parallel to the [001] direction; the dimethylformamide mol-
ecules are pendent from the chain, but they play no other role
in the hydrogen bonding. Within the chain, R22(8) rings
containing paired N—Hꢀ ꢀ ꢀO hydrogen bonds are centred at
(0, 0, n), where n represents an integer, and these alternate
with R22(16) rings containing paired C—Hꢀ ꢀ ꢀO hydrogen
bonds, which are centred at (0, 0, 12 + n), where n represents an
integer (Fig. 10). These chains are further linked by a ꢀ–ꢀ
stacking interaction to form a sheet parallel to (100).
Experimental
Equimolar quantities of the appropriate 6-aminopyrimidine-5-carb-
aldehyde, 6-amino-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
for (I) and (II) or 6-amino-5-formyl-2-methoxy-3-methylpyrimidin-
4(3H)-one for (III) and (IV), and the appropriate 4-substituted aceto-
phenone 4-RC6H4COCH3, where R is Me for (I), Ph for (II), F for (III)
and MeO for (IV), were mixed in the absence of solvent. Three drops of
BF3–Et2O were added to each mixture, which was then heated in an oil
bath at 443 K for 30 s. The resulting dark-brown liquids were diluted
with ethanol and cooled to ambient temperature. The solid products
were collected by filtration, washed with ethanol and then recrystallized
to give the pure pyrido[2,3-d]pyrimidine derivatives as crystals suitable
for single-crystal X-ray diffraction. For (I), yellow solid, crystallized
from ethanol/DMF, yield 50%, m.p. 458–460 K; HR–MS found:
281.1159; C16H15N3O2 requires: 281.1164. For (II), yellow solid, purified
by column chromatography using chloroform as eluant, and recrys-
tallized from ethanol/DMF, yield 60%, m.p. 506–509 K; HR–MS found:
343.1313; C21H17N3O2 requires: 343.1321. For (III), yellow solid, crys-
tallized from DMF, yield 60%, m.p. 568–570 K; HRMS found: 271.0752;
C14H10FN3O2 requires: 271.0757. For (IV), yellow solid, crystallized
from DMF, yield 70%, m.p. >573 K. HR–MS found: 283.0966;
C15H13N3O3 requires: 283.0957.
Figure 9
A stereoview of part of the crystal structure of QOQQIW (Sarkhel et al.,
2001), showing the formation of a ꢀ-stacked pair of C(10) hydrogen-
bonded chains. The original atom coordinates have been employed and,
for the sake of clarity, H atoms not involved in the motif shown have been
omitted.
Compound (I)
Crystal data
C16H15N3O2
Mr = 281.31
Triclinic, P1
a = 6.9953 (5) A
˚
b = 7.9221 (7) A
c = 12.5140 (13) A
ꢁ = 93.466 (4)ꢃ
ꢂ = 92.993 (6)ꢃ
ꢃ = 101.152 (6)ꢃ
3
˚
V = 677.71 (11) A
Z = 2
˚
Mo Kꢁ radiation
ꢄ = 0.09 mmꢁ1
T = 120 K
0.20 ꢄ 0.10 ꢄ 0.02 mm
˚
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.972, Tmax = 0.998
11686 measured reflections
2989 independent reflections
1699 reflections with I > 2ꢅ(I)
Rint = 0.080
Figure 10
Refinement
A stereoview of part of the crystal structure of XEBCUD (Wang et al.,
2006), showing the formation of a chain of hydrogen-bonded R22(8) and
R22(16) rings. The original atom coordinates have been employed and, for
the sake of clarity, H atoms not involved in the motifs shown have been
omitted, as have the dimethylformamide molecules.
R[F2 > 2ꢅ(F2)] = 0.065
wR(F2) = 0.200
S = 1.03
193 parameters
H-atom parameteꢁrs3 constrained
˚
Áꢆmax = 0.45 e A
Áꢆmin = ꢁ0.35 e A
ꢁ3
˚
2989 reflections
ꢂ
Acta Cryst. (2009). C65, o134–o139
Trilleras et al.
C16H15N3O2, C21H17N3O2, C14H10FN3O2 and C15H13N3O3 o137

organic compounds
Compound (II)
Refinement
R[F2 > 2ꢅ(F2)] = 0.057
wR(F2) = 0.147
S = 1.14
1439 reflections
192 parameters
1 restraint
H-atom parameteꢁrs3 constrained
Crystal data
˚
3
Áꢆmax = 0.36 e A
˚
C21H17N3O2
Mr = 343.38
Monoclinic, P21=c
˚
a = 7.2314 (5) A
b = 17.5834 (18) A
˚
c = 12.4864 (15) A
ꢂ = 97.782 (8)ꢃ
V = 1573.1 (3) A
Z = 4
ꢁ3
˚
Áꢆmin = ꢁ0.39 e A
Mo Kꢁ radiation
ꢄ = 0.10 mmꢁ1
T = 120 K
0.45 ꢄ 0.27 ꢄ 0.15 mm
˚
Table 1
Selected interplanar angles (ꢃ) for (I)–(IV).
(I)
(II)
(III)
15.3 (2)
(IV)
Data collection
Pyridine/C71–C76
C71–C76/C81–C86
Pyridine/C81–C86
19.7 (2)
12.8 (2)
33.0 (2)
20.3 (2)
21.7 (2)
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.947, Tmax = 0.986
40144 measured reflections
3612 independent reflections
1851 reflections with I > 2ꢅ(I)
Rint = 0.092
Table 2
Hydrogen bonds and short intramolecular contacts (A, ) for (I)–(IV).
ꢃ
˚
Refinement
Cg represents the centroid of the C71–C76 ring.
R[F2 > 2ꢅ(F2)] = 0.073
wR(F2) = 0.244
S = 1.03
237 parameters
H-atom parameteꢁrs3 constrained
Compound
D—Hꢀ ꢀ ꢀA
C5—H5ꢀ ꢀ ꢀO4i
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
˚
Áꢆmax = 0.48 e A
ꢁ3
(I)
0.95
2.39
3.306 (3)
161
˚
3612 reflections
Áꢆmin = ꢁ0.34 e A
(II)
C75—H75ꢀ ꢀ ꢀO2ii
0.95
0.95
2.39
2.48
3.294 (3)
2.805 (4)
158
100
C76—H76ꢀ ꢀ ꢀN8
Compound (III)
(III)
(IV)
N1—H1ꢀ ꢀ ꢀO4iii
C76—H76ꢀ ꢀ ꢀN8
N1—H1ꢀ ꢀ ꢀO4iv
C72—H72ꢀ ꢀ ꢀCgv
C75—H75ꢀ ꢀ ꢀCgvi
0.88
0.95
2.08
2.42
2.874 (4)
2.753 (5)
149
100
Crystal data
3
0.88
0.95
0.95
1.99
2.65
2.75
2.765 (5)
3.448 (5)
3.548 (5)
146
142
142
˚
V = 1155.7 (3) A
Z = 4
C14H10FN3O2
Mr = 271.25
Orthorhombic, P212121
˚
Mo Kꢁ radiation
ꢄ = 0.12 mmꢁ1
T = 120 K
0.10 ꢄ 0.10 ꢄ 0.10 mm
Symmetry codes: (i) ꢁx; ꢁy; ꢁz þ 1; (ii) ꢁx þ 1; y þ 12 ; ꢁz þ ; (iii) ꢁx þ 1; y þ ,
3
2
1
2
a = 6.7658 (8) A
˚
ꢁz þ ; (iv) x þ 1; y; z; (v) x ꢁ 12 ; ꢁy; z; (vi) x þ 21 ; ꢁy þ 1; z.
1
2
b = 12.978 (2) A
˚
c = 13.162 (2) A
With the exception of the methyl H atoms bonded to C31 in
compound (III), all H atoms were clearly located in difference maps.
H atoms bonded to C31 in compound (III) were placed in calculated
positions, and all H atoms were then treated as riding atoms in
geometrically idealized positions. The H atoms bonded to three-
connected C atoms in aromatic or heteroaromatic rings were placed
along the external bisectors of the ring angles, with C—H distances of
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.968, Tmax = 0.988
11820 measured reflections
1538 independent reflections
833 reflections with I > 2ꢅ(I)
Rint = 0.164
˚
0.95 A and with Uiso(H) = 1.2Ueq(C). H atoms bonded to ring N
atoms were placed along the external bisectors of the ring angles, with
˚
N—H distances of 0.88 A and with Uiso(H) = 1.2Ueq(N). The methyl
Refinement
R[F2 > 2ꢅ(F2)] = 0.064
wR(F2) = 0.155
S = 1.00
182 parameters
H-atom parameteꢁrs3 constrained
groups were all permitted to rotate about the adjacent C—X bonds
(X = C or O) but not to tilt, with all of the X—C—H and H—C—H
angles held fixed in each such group, and with C—H distances of
˚
Áꢆmax = 0.29 e A
ꢁ3
˚
1538 reflections
Áꢆmin = ꢁ0.36 e A
˚
0.98 A and with Uiso(H) = 1.5Ueq(C). In the absence of significant
resonant scattering, the Friedel-equivalent reflections were merged
for compounds (III) and (IV). Hence, the absolute configuration of
the molecules in (III) and the correct orientation of the structure of
(IV) with respect to the polar-axis direction are both undetermined.
For all compounds, data collection: COLLECT (Hooft, 1999); cell
refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction:
EVALCCD (Duisenberg et al., 2003); program(s) used to solve
structure: SIR2004 (Burla et al., 2005); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
PLATON (Spek, 2003); software used to prepare material for
publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
Compound (IV)
Crystal data
3
˚
V = 1249.2 (5) A
Z = 4
C15H13N3O3
Mr = 283.28
Orthorhombic, Pca21
˚
Mo Kꢁ radiation
ꢄ = 0.11 mmꢁ1
T = 120 K
0.28 ꢄ 0.24 ꢄ 0.22 mm
a = 6.6312 (11) A
˚
b = 6.8121 (15) A
˚
c = 27.653 (7) A
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.961, Tmax = 0.977
8019 measured reflections
1439 independent reflections
1181 reflections with I > 2ꢅ(I)
Rint = 0.051
´
´
The authors thank ‘Servicios Tecnicos de Investigacion of
Universidad de Jaen’ and the staff for the data collections for
´
´ ´
(II) and (IV). JC thanks the Consejerıa de Innovacion, Ciencia
ꢂ
o138 Trilleras et al. C16H15N3O2, C21H17N3O2, C14H10FN3O2 and C15H13N3O3
Acta Cryst. (2009). C65, o134–o139

organic compounds
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