organic compounds
Ê
C16A, and by � 0.05 (2) and 1.31 (2) A for C15B and C16B,
Table 2
CÐHÁ Á ÁO interactions (A, ).
Ê
ꢀ
respectively. In the other ethyl carboxylate group, atom O3
Ê
deviates by � 0.118 (4) A from the C10/C11/O2/C12/C13
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
ꢀ
plane, which makes an angle of 50.3 (3) with the pyrrolidine-
ring plane.
The molecular structure of (I) is maintained by an intra-
i
C8ÐH8AÁ Á ÁO4
C9ÐH9AÁ Á ÁO2
0.97
0.98
0.97
0.93
0.93
2.54
2.36
2.59
2.57
2.47
3.415 (4)
2.718 (3)
3.443 (5)
3.496 (5)
3.327 (4)
150
100
147
171
154
ii
i
C12ÐH12BÁ Á ÁO3
Ê
molecular interaction between C9 and O2 [2.718 (3) A]. In the
C18ÐH18AÁ Á ÁO4
iii
C20ÐH20BÁ Á ÁO1
crystal, the molecules form four CÐHÁ Á ÁO interactions
Symmetry codes: (i) � x; � y; 1 � z; (ii) � 1 � x; � y; � z; (iii) 1 x; 1 y; z.
(Table 2) which, together with van der Waals interactions,
stabilize the crystal structure (Fig. 2).
Re®nement
2
Re®nement on F
2
H-atom parameters constrained
2 2 2
2
R[F > 2ꢅ(F )] = 0.059
wR(F ) = 0.161
S = 0.95
w = 1/[ꢅ (F
where P = (F
(Á/ꢅ)max < 0.001
o
) + (0.096P) ]
Experimental
2
2 2
+ 2F )/3
o c
The title compound was synthesized (overall yield 80%) from
p-¯uoroaniline (Aldrich) through the formation of arylamino-
malonate (bromoethylmalonate) and condensation with 3-(2-thi-
enyl)acrloyl chloride in the presence of triethylamine.
Ê
� 3
3
2
391 re¯ections
73 parameters
Áꢆmax = 0.35 e A
Áꢆmin = � 0.44 e AÊ
� 3
After checking their presence in the difference map, all H atoms
were ®xed geometrically and allowed to ride on their parent atoms
Crystal data
Ê
CÐH = 0.93±0.98 A). Due to the large fraction of weak data at
(
C
M
20
H
20FNO
= 405.43
Triclinic, P1
a = 9.6560 (2) A
5
S
Z = 2
= 1.369 Mg m
Mo Kꢁ radiation
ꢀ
�
3
higher angles, 2ꢃ was limited to a maximum of 50 .
r
D
x
Data collection: SMART (Siemens, 1996); cell re®nement: SAINT
Siemens, 1996); data reduction: SAINT; program(s) used to solve
Ê
Cell parameters from 3864
re¯ections
(
Ê
b = 10.1195 (1) A
Ê
c = 12.3126 (2) A
ꢁ
ꢂ = 92.659 (1)
ꢀ = 115.856 (1)
V = 983.58 (3) A
structure: SHELXTL (Sheldrick, 1997); program(s) used to re®ne
structure: SHELXTL; molecular graphics: SHELXTL; software used
to prepare material for publication: SHELXTL, PARST (Nardelli,
1995) and PLATON (Spek, 1990).
ꢀ
ꢃ = 1.8±28.6
ꢀ
� 1
= 110.704 (1)
ꢀ
ꢄ = 0.21 mm
T = 293 (2) K
ꢀ
Ê
Slab, colourless
0.42 Â 0.32 Â 0.16 mm
3
The authors would like to thank the Malaysian Government
and Universiti Sains Malaysia for research grant R&D No.
305/PFIZIK/610961, and AU wishes to thank Universiti Sains
Malaysia for a Visiting Postdoctoral Fellowship.
Data collection
Siemens SMART CCD area-
detector diffractometer
3391 independent re¯ections
2358 re¯ections with I > 2ꢅ(I)
!
scans
Absorption correction: empirical
SADABS; Sheldrick, 1996)
min = 0.919, Tmax = 0.968
604 measured re¯ections
Rint = 0.045
ꢀ
ꢃ
max = 25.0
(
T
h = � 9 ! 11
k = � 11 ! 12
l = � 11 ! 14
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK1510). Services for accessing these data are
described at the back of the journal.
5
References
Table 1
Selected geometric parameters (A, ).
Ê
ꢀ
Baldwin, J. E., Chan, M. F., Gallecher, G. & Otsnka, M. (1984). Tetrahedron,
40, 4513±4517.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354±1358.
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Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
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S1ÐC17
F1ÐC3
O1ÐC7
O2ÐC11
O2ÐC12
O3ÐC11
O4ÐC14
O5ÐC14
N1ÐC7
1.704 (3)
1.724 (2)
1.361 (3)
1.213 (3)
1.315 (3)
1.465 (3)
1.194 (3)
1.201 (3)
1.318 (3)
1.372 (3)
N1ÐC6
1.442 (3)
1.471 (3)
1.503 (4)
1.533 (3)
1.497 (3)
1.573 (3)
1.531 (3)
1.369 (4)
1.419 (4)
1.337 (5)
N1ÐC10
C7ÐC8
C8ÐC9
C9ÐC17
C9ÐC10
C10ÐC11
C17ÐC18
C18ÐC19
C19ÐC20
2
, 1417.
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Sivakumar, K., Fun, H.-K., Ray, J. K., Roy, B. C. & Nigam, G. D. (1995a). Acta
Cryst. C51, 1942±1944.
C20ÐS1ÐC17
C7ÐN1ÐC6
N1ÐC7ÐC8
92.45 (14)
121.00 (19)
108.0 (2)
C8ÐC9ÐC10
N1ÐC10ÐC9
C9ÐC17ÐS1
102.68 (18)
101.06 (18)
121.57 (18)
Sivakumar, K., Fun, H.-K., Ray, J. K., Roy, B. C. & Nigam, G. D. (1995b). Acta
Cryst. C51, 2444±2446.
Spek, A. L. (1990). Acta Cryst. A46, C-34.
C12ÐO2ÐC11ÐC10
175.9 (2)
ꢁ
1442 Anwar Usman et al.
C
20
H20FNO
5
S
Acta Cryst. (2001). C57, 1441±1442