organic compounds
Table 1
Selected geometric parameters (A, ).
of April 2002; Allen, 2002), gives 68 hits for ClÁ Á ÁO(ring)
contacts. Of these contacts, only three are less than the sum of
the van der Waals radii, and all the others range between 3.294
ꢀ
Ê
C3ÐC31
1.415 (3)
177.9 (2)
C31ÐN31
1.151 (3)
Ê
Ê
and 4.247 A. Thus, contacts less than 3.27 A are rare. In
3,4,5,6,7-pentachloro-8-oxatricyclo[4.3.0.03,7]non-4-ene (ref-
code JEMXUU; Shnulin et al., 1989), the ClÁ Á ÁO distance is
N31ÐC31ÐC3
ꢀ
Ê
3.049 A and the angle at Cl is 153.8 . In N-(2,6-dichloro-
phenyl)-1,2-epimino-3,4-epoxycyclopentane (refcode KOJ-
Ê
and the angle at Cl is 165.7ꢀ. In N-(2,2-dichlorovinyl)-1,2-
epimino-4,5-epoxy-cyclopentane (refcode XZCVIN10; Van
Table 2
Hydrogen-bonding geometry (A, ).
JUO; Rousselle et al., 1991), the ClÁ Á ÁO distance is 3.114 A
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Ê
Meerssche et al., 1977), the ClÁ Á ÁO distance is 2.961 A and the
N2ÐH2AÁ Á ÁO5i
0.92
0.92
2.00
2.26
2.894 (3)
3.118 (3)
165
155
angle at Cl is 179.0ꢀ. It is also worth noting that in (I) and the
compounds cited above, the angles at Cl are all greater than
153ꢀ, whereas the angles at Cl for the rest of the compounds in
the search range between 60 and 170ꢀ, randomly.
N2ÐH2BÁ Á ÁN31ii
Symmetry codes: (i) 1 x; 12 y; 21 z; (ii) x; 21 y; 12 z.
There are no unusual bond lengths and angles in (I), which
are in agreement with those found in (II).
therefore the use of AFIX 93 would give a false position for the
amino H atoms.
Data collection: KappaCCD Server Software (Nonius, 1997); cell
re®nement: DENZO±SMN (Otwinowski & Minor, 1997); data
reduction: DENZO±SMN; program(s) used to solve structure:
SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:
SHELXL97; molecular graphics: PLATON (Spek, 2002); software
used to prepare material for publication: SHELXL97 and
PRPKAPPA (Ferguson, 1999).
Experimental
A solution of p-chlorobenzylidenemalonodinitrile (1 mmol) and 5,5-
dimethylcyclohexane-1,3-dione (1 mmol) in absolute ethanol (10 ml)
was heated under re¯ux for 6 h according to the method of Tu et al.
(2001). The resulting precipitate was isolated by ®ltration, washed
with ethanol, dried and recrystallized from ethanol (yield 80%, m.p.
491 K). Analysis, required for C18H17ClN2O2: C 65.8, H 5.2, N 8.5%;
found: C 65.7, H 5.2, N 8.6%.
The X-ray data were collected at the EPSRC X-ray Crys-
tallographic Service, University of Southampton, England; the
authors thank the staff for all their help and advice. JNL
thanks NCR Self-Service, Dundee, for grants which have
provided computing facilities for this work. MN, AS and JC
Crystal data
3
C18H17ClN2O2
Mr = 328.79
Monoclinic, P21=c
Dx = 1.410 Mg m
Mo Kꢁ radiation
Cell parameters from 3487
re¯ections
Â
thank the Ministerio de Educacion, Cultura y Deportes
(Programa de Cooperacion con Iberoamerica, AECI), Spain,
Ê
a = 9.3867 (3) A
Â
Â
b = 16.5328 (5) A
ꢂ = 3.2±27.5ꢀ
ꢃ = 0.26 mm
T = 120 (1) K
Ê
for ®nancial support of part of this work.
1
Ê
c = 11.3189 (3) A
ꢀ = 118.118 (2)ꢀ
V = 1549.25 (8) A
Z = 4
3
Ê
Plate, colourless
0.20 Â 0.08 Â 0.08 mm
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GD1236). Services for accessing these data are
described at the back of the journal.
Data collection
Nonius KappaCCD area-detector
diffractometer
' scans, and ! scans with ꢄ offsets
Absorption correction: multi-scan
(DENZO±SMN; Otwinowski &
Minor, 1997)
3487 independent re¯ections
2262 re¯ections with I > 2ꢅ(I)
Rint = 0.066
References
Allen, F. H. (2002). Acta Cryst. B58, 380±388.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Gilli, G. (1994). Fundamentals of Crystallography, edited by G. Giacovazzo,
p. 466. Oxford University Press.
ꢂ
max = 27.5ꢀ
h = 12 ! 12
k = 18 ! 21
l = 14 ! 13
Tmin = 0.950, Tmax = 0.980
12 189 measured re¯ections
Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius
BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307±326. New York: Academic Press.
Rousselle, D., Francotte, E., Feneau-Dupont, J., Tinant, B., Declercq, J. P. &
Viehe, H. G. (1991). Tetrahedron, 47, 8323±8330.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Re®nement
Re®nement on F2
R[F2 > 2ꢅ(F2)] = 0.047
wR(F2) = 0.130
S = 1.02
3487 re¯ections
210 parameters
H-atom parameters constrained
w = 1/[ꢅ2(Fo2) + (0.066P)2]
where P = (Fo2 + 2Fc2)/3
(Á/ꢅ)max < 0.001
3
Ê
Áꢆmax = 0.29 e A
3
Ê
0.36 e A
Áꢆmin
=
È
Gottingen, Germany.
Shnulin, A. N., Ismailov, S. A. & Shil'nikov, V. I. (1989). Zh. Strukt. Khim. 30,
124±129.
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The Netherlands.
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Cryst. E57, o358±o359.
Van Meerssche, M., Germain, G., Declercq, J. P., Bodart-Gilmont, J., Viehe,
Space group P21/c was deduced from the systematic absences. H
atoms were treated as riding atoms, with CÐH distances in the range
Ê
Ê
0.95±1.00 A and NÐH distances of 0.92 A. These latter atoms were
DFIXed to this value based on positions found in a difference map,
and then AFIXed in the ®nal cycles (SHELXL97; Sheldrick, 1997). It
is worth noting that the amino group is not planar in (I), and
Â
H. G., Merenyi, R. & Francotte, E. (1977). Acta Cryst. B33, 3553±3554.
ꢁ
Acta Cryst. (2003). C59, o38±o39
John N. Low et al. C18H17ClN2O2 o39