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Journal ArticleDOI

1,5-bis(3-bromo-2-thienyl)-3-(3-nitrophenyl)-pentane-1,5-dione

TL;DR: In the title compound, C19H13Br2NO4S2, the two bromo-thienyl rings have different orientations with respect to the carbonyl groups as discussed by the authors.
Abstract: In the title compound, C19H13Br2NO4S2, the two bromo­thienyl rings have different orientations with respect to the carbonyl groups. The nitro group is almost coplanar with the benzene ring to which it is attached.

Summary (1 min read)

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

Key indicators

  • For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
  • In the title compound, C19H13Br2NO4S2, the two bromothienyl rings have different orientations with respect to the carbonyl groups.
  • The nitro group is almost coplanar with the benzene ring to which it is attached.

Comment

  • Today, crystals play an important role in electronic and photonic industries, such as in the production of high-effi- ciency photovoltaic cells, fabrication of bright and long-lasting light emitting diodes (LEDs) and in liquid crystal displays (LCDs).
  • The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application.
  • The molecular structure of the title compound is shown in Fig.
  • The nitro group is almost coplanar with the benzene ring to which it is attached.

Experimental

  • The reaction mixture was then brought to room temperature and stirred for 4 h.
  • The solid that precipitated was filtered off, washed with water, dried and recrystallized from an acetone/methanol mixture (1:1) (yield 75%, m.p. 439–441 K).

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organic papers
o4554 Yathirajan et al.
C
19
H
13
Br
2
NO
4
S
2
doi:10.1107/S1600536806036993 Acta Cryst. (2006). E62, o4554–o4555
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
1,5-Bis(3-bromo-2-thienyl)-3-(3-nitrophenyl)-
pentane-1,5-dione
H. S. Yathirajan,
a
B. K. Sarojini,
b
B. V Ashalatha,
c
B. Narayana
c
and Michael Bolte
d
*
a
Department of Studies in Chemistry, University
of Mysore, Manasagangotri, Mysore 570 006,
India,
b
Department of Chemistry, P.A. College
of Engineering, Nadupadavu, Mangalore 574
153, India,
c
Department of Chemistry,
Mangalore University, Mangalagangotri 574
199, India, and
d
Institut fu
¨
r Anorganische
Chemie, J. W. Goethe-Universita
¨
t Frankfurt,
Max-von-Laue-Strasse 7, 60438 Frankfurt/Ma in,
Germany
Correspondence e-mail:
bolte@chemie.uni-frankfurt.de
Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C–C) = 0.005 A
˚
R factor = 0.042
wR factor = 0.112
Data-to-parameter ratio = 17.4
For details of how these key indicators were
automatically derived from the article, see
http://journals.iucr.org/e.
Received 21 August 2006
Accepted 12 September 2006
# 2006 International Union of Crystallography
All rights reserved
In the title compound, C
19
H
13
Br
2
NO
4
S
2
, the two bromothienyl
rings have different orientations with respect to the carbonyl
groups. The nitro group is almost coplanar with the benzene
ring to which it is attached.
Comment
Today, crystals play an important role in electronic and
photonic industries, such as in the production of high-effi-
ciency photovoltaic cells, fabrication of bright and long-lasting
light emitting diodes (LEDs) and in liquid crystal disp lays
(LCDs). Crystal growth is a multidisciplinary field, which
demands collaboration of chemical and process engineers,
electrical and mechanical engineers, instrumentation engi-
neers, materials scientists, numerical simulation specialists,
physicists and crystallographers (Tareen & Kutty, 2001). The
present day demand is for large and high-quality ferroelectric,
piezoelectric single crystals with minimum defects and inho-
mogeneities. The important goal of crystal growth is the
improvement of microscopic and macroscopic homogeneity,
which is a necessity for any application. The crystal structures
of 3-hydroxy-1,3-bis(2-thienyl)prop-2-en-1-one (Baxter et al.,
1990) and 1-(4-chloropheny l)-3-(2-thienyl)prop-2-en-1-one
(Ng et al., 2006) have been reported. In continuation of our
work on crystal structures of new organic compounds and
chalcones (Yathirajan et al., 2006a,b), the title compound has
been synthesized and its crystal structure is reported.
The molecular structure of the title compound is shown in
Fig. 1. Bond lengths and angles can be regarded as normal
(Cambridge Structural Database, Version 5.27, November
2005, updated August 2006; Mogul, Version 1.1; Allen, 2002).
Whereas one of the carbonyl groups is trans to the nearest C—
S bond, the other is cis configured (Table 1). The nitro group is
almost coplanar with the benzene ring to which it is attached.
Experimental
2-Acetyl-3-bromothiophene (20 g, 0.096 mol) in methanol (50 ml)
was mixed with 3-nitrobenzaldehyde (7.2 g, 0.048 mol) and the

mixture was treated with 10 ml of a 30% potassium hydroxide solu-
tion at 278 K. The reaction mixture was then brought to room
temperature and stirred for 4 h. The solid that precipitated was
filtered off, washed with water, dried and recrystallized from an
acetone/methanol mixture (1:1) (yield 75%, m.p. 439–441 K).
Analysis for C
19
H
13
Br
2
NO
4
S
2
: found (calculated): C 41.91 (42.01), H
2.32 (2.41), N 2.46 (2.58), S 11.72 (11.80)%.
Crystal data
C
19
H
13
Br
2
NO
4
S
2
M
r
= 543.24
Monoclinic, Cc
a = 17.5329 (13) A
˚
b = 15.6345 (9) A
˚
c = 7.4723 (6) A
˚
= 96.932 (6)
V = 2033.3 (3) A
˚
3
Z =4
D
x
= 1.775 Mg m
3
Mo K radiation
= 4.22 mm
1
T = 173 (2) K
Rod, colourless
0.26 0.13 0.12 mm
Data collection
Stoe IPDS-II two-circle
diffractometer
! scans
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing,
1995)
T
min
= 0.407, T
max
= 0.632
13028 measured reflections
4431 independent reflections
4195 reflections with I >2(I)
R
int
= 0.058
max
= 27.6
Refinement
Refinement on F
2
R[F
2
>2(F
2
)] = 0.042
wR(F
2
) = 0.112
S = 1.04
4431 reflections
254 parameters
H-atom parameters constrained
w = 1/[
2
(F
o
2
) + (0.0814P)
2
+ 0.7776P]
where P =(F
o
2
+2F
c
2
)/3
(/)
max
< 0.001
max
= 0.61 e A
˚
3
min
= 0.69 e A
˚
3
Extinction correction: SHELXL97
Extinction coefficient: 0.0066 (6)
Absolute structure: Flack (1983),
2083 Friedel pair
Flack parameter: 0.002 (8)
Table 1
Selected torsion angles (
).
O1—N1—C3—C2 3.8 (5)
O2—N1—C3—C4 5.4 (5)
S11—C11—C15—O15 170.7 (3)
S21—C21—C25—O25 2.9 (4)
H atoms were found in a difference map, but placed geometrically
and allowed to ride on their parent C atoms at distances ranging from
0.95 to 1.00 A
˚
and with U
iso
(H) = 1.2U
eq
(C).
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: XP in
SHELXTL-Plus (Sheldrick, 1991); software used to prepare material
for publication: SHELXL97 and PLATON (Spek, 2003).
BKS thanks AICTE, Government of India, New Delhi, for
financial assistance under the project ‘Career Award for
Young Teachers’ (CAYT) scheme and BVA thanks Mangalore
University for permission to carry out the research work.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388.
Baxter, L. A. M., Blake, A. J., Heath, G. A. & Stephenson, T. A. (1990). Acta
Cryst. C46, 508–510.
Blessing, R. H. (1995). Acta Cryst. A51, 33–38.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Ng, S.-L., Patil, P. S., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006).
Acta Cryst. E62, o3200–o3202.
Sheldrick, G. M. (1991). SHELXTL-Plus. Release 4.1. Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin, USA.
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.
Tareen, J. A. K. & Kutty, T. R. N. (2001). A Basic Course in Crystallography.
Hyderabad, India: Universities Press (India) Limited.
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. ( 2006a).
Acta Cryst. E62, o3629–o3630.
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. ( 2006b).
Acta Cryst. E62, o3631–o3632.
organic papers
Acta Cryst. (2006). E62, o4554–o4555 Yathirajan et al.
C
19
H
13
Br
2
NO
4
S
2
o4555
Figure 1
The molecular structure of the title compound with the atom numbering;
displacement ellipsoids are at the 50% probability level.
References
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  • ...…2 + 2Fc 2)/3 ( / )max < 0.001 max = 0.61 e Å 3 min = 0.69 e Å 3 Extinction correction: SHELXL97 Extinction coefficient: 0.0066 (6) Absolute structure: Flack (1983), 2083 Friedel pair Flack parameter: 0.002 (8) structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97…...

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  • ...…+ (0.0814P)2 + 0.7776P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.61 e Å−3 Δρmin = −0.69 e Å−3 Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0066 (6) Absolute structure: Flack (1983) Absolute structure parameter: 0.002 (8) sup-2Acta Cryst....

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"1,5-bis(3-bromo-2-thienyl)-3-(3-nit..." refers methods in this paper

  • ...…IPDS-II two-circle diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) Tmin = 0.407, Tmax = 0.632 13028 measured reflections 4431 independent reflections 4195 reflections with I >…...

    [...]

  • ...…Rod, colourless 0.26 0.13 0.12 mm Data collection Stoe IPDS-II two-circle diffractometer ! scans Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) Tmin = 0.407, Tmax = 0.632 13028 measured reflections 4431 independent reflections 4195 reflections with I > 2 (I) Rint = 0.058…...

    [...]

Frequently Asked Questions (1)
Q1. What are the contributions in this paper?

The crystal structures of 3-hydroxy-1,3-bis ( 2-thienyl ) prop-2-en-1-one ( Baxter et al., 1990 ) and 1- ( 4-chlorophenyl ) -3- ( 2-thienyl ) prop-2-en-1-one ( Ng et al., 2006 ) have been reported. In continuation of their work on crystal structures of new organic compounds and chalcones ( Yathirajan et al., 2006a, b ), the title compound has been synthesized and its crystal structure is reported.