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Journal ArticleDOI

5-Phenyl-1-(2-thienyl)penta-2,4-dien-1-one

01 Jan 2007-Acta Crystallographica Section E-structure Reports Online (International Union of Crystallography)-Vol. 63, Iss: 1

AbstractBoth acyclic double bonds in the title mol­ecule, C15H12OS, are trans configured. Geometric parameters are in the usual ranges.

Topics: Double bond (56%)

Summary (1 min read)

Jump to: [Key indicators][Comment][Experimental] and [Refinement]

Key indicators

  • For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
  • All rights reserved Both acyclic double bonds in the title molecule, C15H12OS, are trans configured.
  • Geometric parameters are in the usual ranges.

Comment

  • , -Unsaturated ketones have been used as starting materials for the synthesis of various chemicals, including plastics, resins, pesticides, dyes and pharmaceuticals (Opdyke, 1973).
  • The synthesis and biological evaluation of cyclopenta[c]thiophene- related compounds as new antitumour agents have been reported (Dallemagne et al., 2002) and the title compound, (I), is a biologically active compound.
  • Chalcones and penta- dienones are found to exhibit non-linear optical activity (Uchida et al., 1998).
  • Bond lengths and angles can be regarded as normal (Allen et al., 1987).
  • The central butadiene unit makes dihedral angles of 19.2 (1) and 16.8 (1) with the thienyl group and the phenyl ring, respec- tively.

Experimental

  • The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989).
  • The compound was purified by recrystallization from ethanol.

Refinement

  • Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
  • BKS thanks AICTE, Government of India, for financial assistance through the Career Award for Young Teachers Scheme and SB thanks the University of Mysore for research facilities.

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organic papers
Acta Cryst. (2007). E63, o61–o62 doi:10.1107/S1600536806050860 Yathirajan et al.
C
15
H
12
OS o61
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
5-Phenyl-1-(2-thienyl)penta- 2,4-dien-1-one
H. S. Yathirajan,
a
S. Bindya,
a
A. Mithun,
b
B. Narayana
b
and
Michael Bolte
c
*
a
Department of Studies in Chemistry, University
of Mysore, Manasagangotri, Mysore 570 006,
India,
b
Department of Chemistry, Mangalore
University, Mangalagangotri 574 199, India,
and
c
Institut fu
¨
r Anorganische Chemie, J. W.
Goethe-Universita
¨
t Frankfurt, Max-von-Laue-
Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail:
bolte@chemie.uni-frankfurt.de
Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C–C) = 0.002 A
˚
R factor = 0.038
wR factor = 0.104
Data-to-parameter ratio = 15.3
For details of how these key indicators were
automatically derived from the article, see
http://journals.iucr.org/e.
Received 24 November 2006
Accepted 24 November 2006
# 2007 International Union of Crystallography
All rights reserved
Both acyclic double bonds in the title molecule, C
15
H
12
OS, are
trans configured. Geometric parameters are in the usual
ranges.
Comment
,-Unsaturated ketones have been used as starting materials
for the synthesis of various chemicals, including plastics, resins,
pesticides, dyes and pharmaceuticals (Opdyke, 1973). The
synthesis and biological evaluation of cyclopenta[c]thiophene-
related compounds as new antitumour agents have been
reported (Dallemagne et al., 2002) and the title compound, (I),
is a biologically active compound. Chalcones and penta-
dienones are found to exhibit non-linear optical activity
(Uchida et al., 1998). The crystal structure of 1,5-bis(4-
chlorophenyl)penta-1,4-dien-3-one has been reported
previously (Butcher et al., 2006). In view of the importance of
pentadienones, the crystal structure of compound (I) is
reported here.
The molecular structure of (I) is shown in Fig. 1. Bond
lengths and angles can be regarded as normal (Allen et al.,
1987). Both acyclic double bonds are trans configured. The
dihedral angle between the two aromatic rings is 4.68 (9)
.The
central butadiene unit makes dihedral angles of 19.2 (1) and
16.8 (1)
with the thienyl group and the phenyl ring, respec-
tively.
Experimental
The title compound was synthesized according to the method
reported in the literature (Furniss et al., 1989). The compound was
Figure 1
The molecular structure of the title compound, with the atom-numbering
scheme. Displacement ellipsoids are drawn at the 50% probability level.

purified by recrystallization from ethanol. Crystals were grown by
slow evaporation of a solution of (I) in ethanol (yield 75%; m.p. 353–
357 K). Analysis, found (calculated) for C
15
H
12
OS: C 74.20%
(74.97%), H 5.08% (5.03%).
Crystal data
C
15
H
12
OS
M
r
= 240.31
Orthorhombic, Pbca
a = 15.5571 (12) A
˚
b = 10.2136 (7) A
˚
c = 15.8883 (11) A
˚
V = 2524.6 (3) A
˚
3
Z =8
D
x
= 1.265 Mg m
3
Mo K radiation
= 0.24 mm
1
T = 173 (2) K
Block, light yellow
0.42 0.35 0.22 mm
Data collection
Stoe IPDSII two-circle
diffractometer
! scans
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing,
1995)
T
min
= 0.909, T
max
= 0.970
10971 measured reflections
2353 independent reflections
2080 reflections with I >2(I)
R
int
= 0.028
max
= 25.6
Refinement
Refinement on F
2
R[F
2
>2(F
2
)] = 0.038
wR(F
2
) = 0.104
S = 1.05
2353 reflections
154 parameters
H-atom parameters constrained
w = 1/[
2
(F
o
2
) + (0.0578P)
2
+ 0.7828P]
where P =(F
o
2
+2F
c
2
)/3
(/)
max
= 0.001
max
= 0.26 e A
˚
3
min
= 0.34 e A
˚
3
H atoms were found in a difference map but they were refined
using a riding model, with C—H = 0.95 A
˚
for C
aromatic
and C
methylene
,
or 0.98 A
˚
for methyl groups, and with U
iso
(H)=1.2U
eq
(C), or
1.5U
eq
(C
methyl
).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement:
X-AREA; data reduction: X-AREA; program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine
structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
PLATON (Spek, 2003); software used to prepare material for
publication: SHELXL97 and PLATON.
BKS thanks AICTE, Government of India, for financial
assistance through the Career Award for Young Teachers
Scheme and SB thanks the University of Mysore for research
facilities.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Blessing, R. H. (1995). Acta Cryst. A51, 33–38.
Butcher, R. J., Yathirajan, H. S., Anilkumar, H. G., Sarojini, B. K. & Narayana,
B. (2006). Acta Cryst. E62, o1659–o1661.
Dallemagne, P., Khanh, L. P., Alsadi, A., Renault, O., Varlet, I., Collot, V. ,
Bureau, R. & Rault, S. (2002). Bioorg. Med. Chem. 10, 2185–2191.
Furniss, B. S., Hannaford, A. J., Smith, P. W. G. & Tatchell, A. R. (1989).
Vogel’s Textbook of Practical Organic Chemistry, 5th ed, p. 1034. London:
Longman Group UK Ltd.
Opdyke, D. L. J. (1973). Food Cosmet. Toxicol. 11, 1011–1081.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go
¨
ttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. &
Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140.
organic papers
o62 Yathirajan et al.
C
15
H
12
OS Acta Cryst. (2007). E63, o61–o62
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Frequently Asked Questions (1)
Q1. What are the contributions in this paper?

The synthesis and biological evaluation of cyclopenta [ c ] thiophenerelated compounds as new antitumour agents have been reported ( Dallemagne et al., 2002 ) and the title compound, ( I ), is a biologically active compound. The crystal structure of 1,5-bis ( 4chlorophenyl ) penta-1,4-dien-3-one has been reported previously ( Butcher et al., 2006 ). In view of the importance of pentadienones, the crystal structure of compound ( I ) is reported here.