Four products from the cyano-acetyl-ation of pyrimidines: Hydrogen-bonded dimers, π-stacked hydrogen-bonded chains and hydrogen-bonded chains of edge-fused rings

Article abstract of DOI:10.1107/S0108270108003557

The mol-ecules of 2-[6-amino-3-methyl-2-(methyl-sulfanyl)-4-oxo-3,4- dihydro-pyrimidin-5-yl-carbonyl]-acetonitrile, C9H10N4O2S, (I), are linked in pairs by N - H...O hydrogen bonds to form cyclic centrosymmetric R 2 ²(4) dimers. Similar dimers formed by 2-(6-amino-1,3-dimethyl-2,4- dioxo-1,2,3,4-tetra-hy-dro-pyrimidin-5-yl-carbonyl)-acetonitrile, C9H10N4O3, (II), are reinforced by paired N - H...N hydrogen bonds and linked into chains of rings by C - H...O hydrogen bonds. The mol-ecules of 2-cyano-N-[6-meth-oxy-2-(methyl-sulfanyl)-pyrimidin-4-yl]-acetamide, C9H10N4O2S, (III), are linked into simple C(6) chains by an N - H...N hydrogen bond, and the chains are weakly linked into sheets by a π-π stacking inter-action. A combination of one two-centre N - H...N hydrogen bond and one three-centre C - H...(N,O) hydrogen bond links the mol-ecules of 2-cyano-N-[6-chloro-2-(methyl-sulfanyl)-pyrimidin-4-yl]-acetamide, C8H7ClN4OS, (IV), into a chain of alternating edge-fused R 2 ¹(6) and R 1 ²(6) rings. The crystal structures reported in this study, and those of some related examples from the recent literature, show a wide variation in hydrogen-bonded aggregation consequent upon rather small changes in molecular constitution.

Full text of DOI:10.1107/S0108270108003557

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
ones are used as substrates, substitution does indeed occur at
C5 to provide derivatives such as title compounds (I) and (II)
(Figs. 1 and 2). However, when the substrates are aromatic
pyrimidines, no ring substitution occurs. Instead, acylation
occurs at the exocyclic amino group, giving products such as
title compounds (III) and (IV) (Figs. 3 and 4). We report here
the molecular and supramolecular structures of compounds
(I)–(IV), which exhibit a range of different hydrogen-bonded
structures, and we compare the structure of (III) with that of
the closely related analogue, (V) (Low et al., 1996), and with
that of (VI) (Lynch & McClenaghan, 2001).
ISSN 0108-2701
Four products from the cyanoacetyl-
ation of pyrimidines: hydrogen-
bonded dimers, p-stacked hydrogen-
bonded chains and hydrogen-bonded
chains of edge-fused rings
Jorge Trilleras,a John N. Low,b Justo Cobo,c Antonio
Marchalc and Christopher Glidewelld*
a
´
Departamento de Quımica, Universidad de Valle, AA 25360 Cali, Colombia,
bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen
c
´
´
´
AB24 3UE, Scotland, Departamento de Quımica Inorganica y Organica,
Universidad de Jaen, 23071 Jaen, Spain, and dSchool of Chemistry, University of
´
´
St Andrews, Fife KY16 9ST, Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 13 December 2007
Accepted 1 February 2008
Online 9 February 2008
The molecules of 2-[6-amino-3-methyl-2-(methylsulfanyl)-4-
oxo-3,4-dihydropyrimidin-5-ylcarbonyl]acetonitrile, C9H10N4-
O2S, (I), are linked in pairs by N—Hꢀ ꢀ ꢀO hydrogen bonds to
form cyclic centrosymmetric R22(4) dimers. Similar dimers
formed by 2-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahy-
dropyrimidin-5-ylcarbonyl)acetonitrile, C9H10N4O3, (II), are
reinforced by paired N—Hꢀ ꢀ ꢀN hydrogen bonds and linked
into chains of rings by C—Hꢀ ꢀ ꢀO hydrogen bonds.
The molecules of 2-cyano-N-[6-methoxy-2-(methylsulfanyl)-
pyrimidin-4-yl]acetamide, C9H10N4O2S, (III), are linked into
simple C(6) chains by an N—Hꢀ ꢀ ꢀN hydrogen bond, and the
chains are weakly linked into sheets by a ꢀ–ꢀ stacking
interaction. A combination of one two-centre N—Hꢀ ꢀ ꢀN
hydrogen bond and one three-centre C—Hꢀ ꢀ ꢀ(N,O) hydrogen
bond links the molecules of 2-cyano-N-[6-chloro-2-(methyl-
sulfanyl)pyrimidin-4-yl]acetamide, C8H7ClN4OS, (IV), into a
chain of alternating edge-fused R21(6) and R12(6) rings. The
crystal structures reported in this study, and those of some
related examples from the recent literature, show a wide
variation in hydrogen-bonded aggregation consequent upon
rather small changes in molecular constitution.
In each of compounds (I) and (II), the exocyclic carbonyl
group is nearly coplanar with the ring, with a deviation of
carbonyl atom O51 from the mean plane of the ring of only
˚
˚
0.080 (2) A in (I) and 0.018 (2) A in (II); this is probably
associated both with the polarization of the molecular–elec-
tronic structure, discussed below, and with an intramolecular
N—Hꢀ ꢀ ꢀO hydrogen bond (Table 2), which is charge-assisted
(Gilli et al., 1994) as a consequence of the polarization. In each
of (III) [which is isomeric with (I)], (IV) and (V), the
conformation of the side chain at C6 may in part be controlled
by a rather short intramolecular C—Hꢀ ꢀ ꢀO contact. Here, the
deviation of carbonyl atom O61 from the ring plane, viz.
˚
˚
0.038 (2) A in (III) and 0.427 (3) A in (IV), may be contrasted
with the exact planarity in (V), where all of the non-H atoms
lie on a mirror plane in the Pnma space group (Low et al.,
1996). The conformation adopted by the methylsulfanyl group
in (IV) differs markedly from the conformations in (I) and
(III) (Figs. 1, 2 and 4, and Table 1), although it is similar to that
in (V).
Comment
As part of a wider programme on the development of
synthetic routes to new heterocyclic systems likely to exhibit
biological activity, we have attempted to develop a route to the
functionalization of the C5 position of pyrimidines. Accord-
ingly, we have investigated the reactions of pyrimidines and
their simple derivatives with cyanoacetic acid in the presence
of acetic anhydride as an activator. When pyrimidin-4(3H)-
The bond distances in compounds (I)–(III) (Table 1) show
some unexpected features. We consider firstly the pair (I) and
Acta Cryst. (2008). C64, o149–o154
doi:10.1107/S0108270108003557
# 2008 International Union of Crystallography o149

organic compounds
(II). In each of compounds (I) and (II), the exocyclic C6—N6
˚
bond is short for its type (mean value 1.353 A; Allen et al.,
1987) and certainly much shorter than the corresponding
bonds in compounds (III) and (IV). In addition, the C5—C6
bond, which is formally a double bond, is long for its type
˚
(expected value 1.331 A; Allen et al., 1987) and is only slightly
shorter than the C4—C5 and C5—C51 bonds, which are both
formally single bonds. Finally, the C51—O51 bond is long for
˚
its type (mean value 1.210 A; Allen et al., 1987), although the
length of the C4—O4 bond is typical of its type. Overall, these
effects are somewhat more marked in (II) than in (I), and they
indicate that polarized forms such as (IIa) and (IIb) (see
scheme below) are contributors to the overall molecular–
electronic structure.
Figure 2
The molecular structure of compound (II), showing the atom-labelling
scheme. Displacement ellipsoids are drawn at the 30% probability level
and H atoms are shown as small spheres of arbitrary radii.
In compound (III), there is some evidence for a measure of
bond fixation within the pyrimidine ring. Thus, the N1—C2
and N3—C4 bonds are slightly shorter than the C2—N3 and
Figure 3
The molecular structure of compound (III), showing the atom-labelling
scheme. Displacement ellipsoids are drawn at the 30% probability level
and H atoms are shown as small spheres of arbitrary radii.
˚
C6—N1 bonds, by ca 0.02 and 0.03 A, respectively, while C5—
˚
C6 is slightly shorter (ca 0.02 A) than C4—C5, indicative of a
modest contribution to the overall structure of the form (IIIa)
in addition to the dominant delocalized form (III). For
compound (IV), this pattern in the C—N bonds is not
apparent, while the C4—C5 and C5—C6 bond distances are
not distinguishable within experimental uncertainty. The
lower precision of the determination precludes any mean-
Figure 1
Figure 4
The molecular structure of compound (I), showing the atom-labelling
scheme. Displacement ellipsoids are drawn at the 30% probability level
and H atoms are shown as small spheres of arbitrary radii.
The molecular structure of compound (IV), showing the atom-labelling
scheme. Displacement ellipsoids are drawn at the 30% probability level
and H atoms are shown as small spheres of arbitrary radii.
ꢁ
o150 Trilleras et al. C9H10N4O2S, C9H10N4O3, C9H10N4O2S and C8H7ClN4OS
Acta Cryst. (2008). C64, o149–o154

organic compounds
Figure 5
Figure 7
Part of the crystal structure of compound (II), showing the formation of a
hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C
atoms have been omitted. Atoms marked with an asterisk (*) are at the
symmetry position (1 ꢂ x, ꢂy, 1 ꢂ z).
Part of the crystal structure of compound (III), showing the formation of
a hydrogen-bonded C(6) chain along [010]. For the sake of clarity, H
atoms bonded to C atoms have been omitted. Atoms marked with an
asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions
(32 ꢂ x, 21 + y, 23 ꢂ z), (32 ꢂ x, ꢂ + y, 32 ꢂ z) and (x, 1 + y, z), respectively.
1
2
Within this dimer, there is a pair of fairly long, possibly
adventitious, N—Hꢀ ꢀ ꢀN hydrogen bonds involving two
symmetry-related cyano N54 atoms as acceptors. The cyclic
dimers formed by (II) are linked into chains of rings by a
single C—Hꢀ ꢀ ꢀO hydrogen bond (eighth entry in Table 2);
atom C52 in the molecule at (x, y, z) acts as donor, via atom
1
H52B, to carbonyl atom O4 in the molecule at (32 ꢂ x, ꢂ y,
2
1 ꢂ z), so forming a centrosymmetric R22(12) motif. Propaga-
tion by inversion of the hydrogen bonds links the molecules of
(II) into a rather complex chain of edge-fused rings running
parallel to the [110] direction (Fig. 6).
The same R22(4) motif as found in (II) is also seen in (I), but
the N—Hꢀ ꢀ ꢀN and C—Hꢀ ꢀ ꢀO contacts in (I) corresponding to
the other intermolecular hydrogen bonds in (II) have Hꢀ ꢀ ꢀA
distances much longer than those in (II) (Table 2), such that
they are not structurally significant (first and fourth entries in
Table 2). Thus, the hydrogen bonding in (I) leads to finite
dimeric units, while that in (II) generates a chain of rings.
In compound (III), a single N—Hꢀ ꢀ ꢀN hydrogen bond links
the molecules related by a 21 screw axis into C(6) chains
running parallel to the [010] direction (Fig. 7), and the
hydrogen-bonded chains are weakly linked into sheets by a
ꢀ–ꢀ stacking interaction (not shown in Fig. 7). The molecules
Figure 6
A stereoview of part of the crystal structure of compound (II), showing
the formation of a hydrogen-bonded chain of rings along [110]. For the
sake of clarity, H atoms not involved in the hydrogen bonding have been
omitted.
ingful metrical comparisons at this level. In compound (V),
which was determined from diffraction data collected at 294 K
(Low et al., 1996), the distances provide no evidence for any
bond fixation in the ring, while in (VI), which crystallizes with
Z0 = 2 (Lynch & McClenaghan, 2001), no obvious pattern can
be discerned in the ring bond distances.
The hydrogen-bonded supramolecular structures of (I) and
(II) show both similarities and differences. In each compound,
a planar three-centre N—Hꢀ ꢀ ꢀ(O)2 hydrogen bond links the
molecules in pairs to form a centrosymmetric dimer char-
acterized by an R22(4) (Bernstein et al., 1995) motif (Fig. 5).
3
at (x, y, z) and (1 ꢂ x, y, ꢂ z) form parts of the hydrogen-
2
3
4
bonded chains around the 21 screw axes along (34, y, ) and
(14, y, 34), respectively. The pyrimidine rings of these molecules
make a dihedral angle of 5.9 (2)ꢃ; the ring centroid separation
˚
˚
is 3.819 (2) A and the interplanar spacing is ca 3.39 A. The
resulting ꢀ–ꢀ stacking interaction thus links two molecules,
ꢁ
Acta Cryst. (2008). C64, o149–o154
Trilleras et al.
C9H10N4O2S, C9H10N4O3, C9H10N4O2S and C8H7ClN4OS o151

organic compounds
pyrimidine for (III) and 6-amino-4-chloro-2-(methylsulfanyl)pyrimi-
dine for (IV) (50 mmol), was added to a solution of cyanoacetic acid
(50 mmol) in acetic anhydride (50 ml) at 323 K. The mixtures were
heated to 358 K for 5 min, whereupon the products started to crys-
tallize. After a further 5 min, the mixtures were allowed to cool to
ambient temperature, and the resulting solid products were collected
by filtration, washed with methanol and dried in air. Recrystallization
from dimethylformamide for (I) and (II) or from ethanol for (III) and
(IV) gave crystals suitable for single-crystal X-ray diffraction.
Analysis for (I): colourless crystals, yield 60%, m.p. 519–520 K
(HRMS: m/z found 238.0524; C9H10N4O2S requires 238.0523); (II):
yellow crystals, yield 87%, m.p. 435–436 K (HRMS: m/z found
222.0742; C9H10N4O3 requires 222.0753); (III): yellow crystals, yield
60%, m.p. 429–430 K (HRMS: m/z found 238.0524; C9H10N4O2S
requires 238.0533); (IV): yellow crystals, yield 70%, m.p. 529–530 K
(HRMS: m/z found 242.0029; C8H735ClN4OS requires 242.0028).
Compound (I)
Crystal data
C9H10N4O2S
Mr = 238.27
Triclinic, P1
ꢃ = 82.654 (4)ꢃ
3
Figure 8
˚
V = 521.48 (3) A
Z = 2
Part of the crystal structure of compound (IV), showing the formation of
a hydrogen-bonded chain of alternating R12(6) and R12(6) rings along [010].
For the sake of clarity, H atoms bonded to atoms C5 and C21 have been
omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand
˚
˚
a = 6.6449 (3) A
Mo Kꢁ radiation
ꢄ = 0.30 mmꢂ1
T = 120 (2) K
0.56 ꢄ 0.33 ꢄ 0.32 mm
b = 8.7262 (3) A
˚
c = 9.4092 (2) A
(&) are at the symmetry positions (1 ꢂ x, 12 + y, 21 ꢂ z), (1 ꢂ x, ꢂ + y, 21 ꢂ z)
1
2
ꢁ = 76.390 (3)ꢃ
ꢂ = 81.079 (2)ꢃ
and (x, 1 + y, z), respectively.
Data collection
related by the twofold rotation axis along (12, y, 43), and
propagation of this interaction by the twofold rotation axes
links the hydrogen-bonded chain along (34, y, 43) (Fig. 7) to those
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.849, Tmax = 0.910
14244 measured reflections
2386 independent reflections
1902 reflections with I > 2ꢅ(I)
Rint = 0.039
3
3
along (14, y, ) and (54, y, ), thereby generating a sheet of ꢀ-
4
4
stacked hydrogen-bonded chains parallel to (001).
As in compound (III), a single N—Hꢀ ꢀ ꢀN hydrogen bond in
(IV) links molecules related by a 21 screw axis into C(6) chains
running parallel to the [010] direction. However, this chain is
reinforced by two further interactions which together form a
planar three-centre C—Hꢀ ꢀ ꢀ(N,O) hydrogen bond, and the
combined effect of all three interactions is the generation of a
chain of edge-fused rings in which R12(6) and R12(6) rings
alternate (Fig. 8 and Table 2). There are no direction-specific
interactions between adjacent chains.
Refinement
R[F2 > 2ꢅ(F2)] = 0.038
wR(F2) = 0.107
S = 1.09
147 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢆmax = 0.37 e A
ꢂ3
˚
2386 reflections
Áꢆmin = ꢂ0.35 e A
Compound (II)
Crystal data
The molecules in compound (V) (Low et al., 1996) are
linked by N—Hꢀ ꢀ ꢀO hydrogen bonds into C(4) chains, and it is
interesting to note the contrast between the hydrogen bonding
in (III) and (V). Although both compounds contain a carbonyl
O atom, this is utilized as a hydrogen-bond acceptor only in
(V), where the cyano group is absent. In both (III) and (IV),
where a cyano group is present, N—Hꢀ ꢀ ꢀO hydrogen bonds
are absent. Compound (VI) contains neither carbonyl nor
cyano groups and each type of molecule is linked into a C(6)
chain by N—Hꢀ ꢀ ꢀN hydrogen bonds, both utilizing a ring N
atom as acceptor (Lynch & McClenaghan, 2001).
3
˚
V = 1892.0 (4) A
Z = 8
C9H10N4O3
Mr = 222.21
Monoclinic, C2=c
Mo Kꢁ radiation
ꢄ = 0.12 mmꢂ1
T = 120 (2) K
0.44 ꢄ 0.31 ꢄ 0.08 mm
˚
a = 22.488 (3) A
˚
b = 5.0709 (5) A
˚
c = 18.6139 (17) A
ꢂ = 116.956 (7)ꢃ
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.952, Tmax = 0.990
20693 measured reflections
2171 independent reflections
1603 reflections with I > 2ꢅ(I)
Rint = 0.042
Refinement
Experimental
R[F2 > 2ꢅ(F2)] = 0.048
wR(F2) = 0.136
S = 1.13
147 parameters
H-atom parameteꢂrs3 constrained
The appropriate pyrimidine, viz. 6-amino-3-methyl-2-(methylsulfan-
yl)pyrimidin-4(3H)-one for (I), 6-amino-1,3-dimethylpyrimidine-
2,4(1H,3H)-dione for (II), 6-amino-4-methoxy-2-(methylsulfanyl)-
˚
Áꢆmax = 0.33 e A
Áꢆmin = ꢂ0.31 e A
ꢂ3
˚
2171 reflections
ꢁ
o152 Trilleras et al. C9H10N4O2S, C9H10N4O3, C9H10N4O2S and C8H7ClN4OS
Acta Cryst. (2008). C64, o149–o154

organic compounds
Table 1
Selected geometric parameters (A, ) for compounds (I)–(IV).
Table 2
Hydrogen bonds and short inter- and intramolecular contacts (A, ) for
compounds (I)–(IV).
ꢃ
ꢃ
˚
˚
(I)
(II)
(III)
(IV)
Compound
(I)
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1—C2
C2—N3
N3—C4
C4—C5
C5—C6
C6—N1
C4—O4
C5—C51
C51—O51
C6—N6
1.308 (2)
1.357 (2)
1.426 (2)
1.439 (2)
1.414 (2)
1.372 (2)
1.227 (2)
1.454 (2)
1.234 (2)
1.333 (2)
1.397 (2)
1.372 (2)
1.400 (2)
1.438 (2)
1.421 (2)
1.368 (2)
1.231 (2)
1.434 (2)
1.243 (2)
1.320 (2)
1.320 (2)
1.343 (2)
1.324 (2)
1.397 (2)
1.375 (2)
1.356 (2)
1.344 (2)
1.339 (4)
1.349 (4)
1.318 (4)
1.379 (5)
1.390 (5)
1.339 (4)
N6—H6Aꢀ ꢀ ꢀN54i
N6—H6Bꢀ ꢀ ꢀO51
N6—H6Bꢀ ꢀ ꢀO51i
C52—H52Bꢀ ꢀ ꢀO4ii
N6—H6Aꢀ ꢀ ꢀN54iii
N6—H6Bꢀ ꢀ ꢀO51
N6—H6Bꢀ ꢀ ꢀO51iii
C52—H52Bꢀ ꢀ ꢀO4iv
N6—H6ꢀ ꢀ ꢀN64v
0.86
0.86
0.86
0.99
0.86
0.86
0.86
0.99
0.86
0.95
0.86
0.95
0.99
0.99
2.69
1.97
2.29
2.78
2.47
1.92
2.17
2.40
2.13
2.30
2.34
2.25
2.33
2.55
3.354 (2)
2.627 (2)
3.019 (2)
3.068 (3)
3.206 (3)
2.586 (2)
2.894 (2)
3.227 (3)
2.993 (3)
2.872 (2)
3.149 (4)
2.816 (5)
2.949 (5)
3.334 (5)
135
132
142
97
(II)
144
134
141
141
176
118
158
117
120
136
1.392 (2)
1.398 (4)
(III)
(IV)
C5—H5ꢀ ꢀ ꢀO61
N6—H6ꢀ ꢀ ꢀN64vi
N1—C2—S2—C21
C6—N6—C61—O61
0.20 (16)
1.00 (15)
2.2 (3)
ꢂ176.6 (3)
ꢂ8.3 (6)
C5—H5ꢀ ꢀ ꢀO61
C62—H62Bꢀ ꢀ ꢀO61vi
C62—H62Bꢀ ꢀ ꢀN64vi
Symmetry codes: (i) 1 ꢂ x; 1 ꢂ y; 1 ꢂ z; (ii) ꢂx; ꢂy; 1 ꢂ z; (iii) 1 ꢂ x; ꢂy; 1 ꢂ z; (iv)
3
2
3
2
ꢂ x; 12 ꢂ y; 1 ꢂ z; (v) ꢂ x; 21 þ y; 23 ꢂ z; (vi) 1 ꢂ x; 21 þ y; 12 ꢂ z.
Compound (III)
Crystal data
3
˚
Crystals of (I) are triclinic. Space group P1 was selected and
C9H10N4O2S
Mr = 238.27
Monoclinic, C2=c
˚
a = 17.106 (3) A
b = 11.8218 (13) A
˚
c = 13.7187 (19) A
ꢂ = 127.836 (8)ꢃ
V = 2191.0 (6) A
Z = 8
confirmed by the structure analysis. For each of (II) and (III), the
systematic absences permitted C2/c and Cc as possible space groups.
In each case, C2/c was selected and confirmed by the structure
analysis. For (IV), space group P21/c was uniquely assigned from the
systematic absences. For three low-angle reflections, viz. 112 in (I),
204 in (III) and 202 in (IV), satisfactory integration could not be
achieved, and they were therefore discarded from the data sets. All H
atoms were located in difference maps and then treated as riding
atoms in geometrically idealized positions, with distances C—H =
Mo Kꢁ radiation
ꢄ = 0.29 mmꢂ1
T = 120 (2) K
0.78 ꢄ 0.52 ꢄ 0.33 mm
˚
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.807, Tmax = 0.911
24464 measured reflections
2505 independent reflections
2078 reflections with I > 2ꢅ(I)
Rint = 0.067
˚
0.95 (aromatic and heteroaromatic), 0.98 (CH3) or 0.99 A (CH2), and
˚
N—H = 0.86 A, and with Uiso(H) = kUeq(carrier), where k = 1.5 for
the methyl groups and 1.2 for all other H atoms.
Refinement
For all compounds, data collection: COLLECT (Nonius, 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: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick,
2008); molecular graphics: PLATON (Spek, 2003); software used to
prepare material for publication: SHELXL97 and PRPKAPPA
(Ferguson, 1999).
R[F2 > 2ꢅ(F2)] = 0.040
wR(F2) = 0.111
S = 1.09
147 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢆmax = 0.34 e A
ꢂ3
˚
2505 reflections
Áꢆmin = ꢂ0.44 e A
Compound (IV)
´
´
The authors thank the Servicios Tecnicos de Investigacion
of the Universidad de Jaen and the staff for data collection. JC
Crystal data
´
3
˚
V = 1020.72 (18) A
Z = 4
Mo Kꢁ radiation
ꢄ = 0.56 mmꢂ1
T = 120 (2) K
C8H7ClN4OS
Mr = 242.69
´
and AM thank the Consejerıa de Innovacion, Ciencia y
Empresa (Junta de Andalucıa, Spain) and the Universidad de
Jaen for financial support. JT thanks COLCIENCIAS and
UNIVALLE (Universidad del Valle, Colombia) for financial
support and for supporting a research visit to the Universidad
´
de Jaen.
´
´
Monoclinic, P21=c
˚
a = 12.8655 (7) A
´
˚
b = 8.4390 (2) A
˚
c = 9.9327 (15) A
ꢂ = 108.827 (13)ꢃ
0.35 ꢄ 0.27 ꢄ 0.17 mm
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.843, Tmax = 0.910
22495 measured reflections
2336 independent reflections
1676 reflections with I > 2ꢅ(I)
Rint = 0.075
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GA3078). Services for accessing these data are
described at the back of the journal.
References
Refinement
R[F2 > 2ꢅ(F2)] = 0.061
wR(F2) = 0.175
S = 1.08
137 parameters
H-atom parameteꢂrs3 constrained
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˚
Áꢆmax = 0.66 e A
ꢂ3
˚
2336 reflections
Áꢆmin = ꢂ0.64 e A
ꢁ
Acta Cryst. (2008). C64, o149–o154
Trilleras et al.
C9H10N4O2S, C9H10N4O3, C9H10N4O2S and C8H7ClN4OS o153

organic compounds
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Acta Cryst. (2008). C64, o149–o154