(2E)-1-(4-Amino-phen-yl)-3-(2-thien-yl)prop-2-en-1-one ethanol hemisolvate.

Abstract

In the title compound, C(13)H(11)NOS·0.5C(2)H(6)O, the chalcone derivative is close to planar, the dihedral angle between the thio-phene and 4-amino-phenyl rings being 3.1 (2)°. The thio-phene ring is disordered over two orientations with occupancies of 0.842 (3) and 0.158 (3). In the crystal structure, mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds. The chains are crosslinked via N-H⋯π inter-actions involving the thio-phene ring. The ethanol solvent mol-ecule is also disordered over two positions, each with an occupancy of 0.25.

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(2E)-1-(4-Aminophenyl)-3-(2-thienyl)-
prop-2-en-1-one ethanol hemisolvate
Hoong-Kun Fun,a*‡ Thawanrat Kobkeatthawinband
Suchada Chantraprommac§
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800
USM, Penang, Malaysia,bDepartment of Chemistry and Center of Excellence for
Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai,
Songkhla 90112, Thailand, andcCrystal Materials Research Unit, Department of
Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla
90112, Thailand
Correspondence e-mail: hkfun@usm.my
Received 11 September 2009; accepted 19 September 2009
Key indicators: single-crystal X-ray study; T = 100 K; mean ?(C–C) = 0.003 A ˚;
disorder in main residue; R factor = 0.061; wR factor = 0.205; data-to-parameter
ratio = 22.5.
In the title compound, C13H11NOS?0.5C2H6O, the chalcone
derivative is close to planar, the dihedral angle between the
thiophene and 4-aminophenyl rings being 3.1 (2)?. The
thiophene ring is disordered over two orientations with
occupancies of 0.842 (3) and 0.158 (3). In the crystal structure,
molecules are linked into chains along the b axis by N—H???O
hydrogen bonds. The chains are crosslinked via N—H????
interactions involving the thiophene ring. The ethanol solvent
molecule is also disordered over two positions, each with an
occupancy of 0.25.
Related literature
For bond-length data, see: Allen et al. (1987). For related
structures, see: Fun et al. (2009); Suwunwong et al. (2009). For
background and applications of chalcones, see: Dimmock et al.
(1999); Go et al. (2005); Ni et al. (2004); Patil & Dharmapra-
kash (2008). For the stability of the temperature controller
used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
C13H11NOS?0.5C2H6O
Mr= 252.32
Orthorhombic, P212121
a = 5.1413 (1) A˚
b = 13.9754 (2) A˚
c = 18.2647 (2) A˚
V = 1312.35 (3) A˚3
Z = 4
Mo K? radiation
? = 0.24 mm?1
T = 100 K
0.56 ? 0.22 ? 0.17 mm
Data collection
Bruker APEXII CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
Tmin= 0.879, Tmax= 0.961
22258 measured reflections
4225 independent reflections
3893 reflections with I > 2?(I)
Rint= 0.026
Refinement
R[F2> 2?(F2)] = 0.061
wR(F2) = 0.205
S = 1.09
4225 reflections
188 parameters
14 restraints
H-atom parameters constrained
??max= 1.04 e A˚?3
??min= ?0.31 e A˚?3
Absolute structure: Flack (1983),
1874 Friedel pairs
Flack parameter: 0.00 (12)
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N1—H1A???O1i
N1—H1B???Cg1ii
Symmetry codes: (i) ?x;y þ1
S1/C10–C13 ring.
D—H H???AD???AD—H???A
0.86
0.86
2.16
2.80
2.931 (3)
3.597 (3)
149
156
2;?z þ1
2; (ii) ?x þ1
2;?y;z þ1
2. Cg1 is the centroid of the
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT
(Bruker, 2005); data reduction: SAINT; program(s) used to solve
structure: SHELXTL (Sheldrick, 2008); program(s) used to refine
structure: SHELXTL; molecular graphics: SHELXTL; software used
to prepare material for publication: SHELXTL and PLATON (Spek,
2009).
TK thanks the Center of Excellence for Innovation in
Chemistry (PERCH-CIC), Commission on Higher Education,
Ministry of Education and the Graduate School, Prince of
Songkla University for financial support. The authors thank
Universiti Sains Malaysia for the Research University Golden
Goose grant No. 1001/PFIZIK/811012.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: CI2908).
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.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,
Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr.
Med. Chem. 6, 1125–1149.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Fun, H.-K., Suwunwong, T., Boonnak, N. & Chantrapromma, S. (2009). Acta
Cryst. E65, o2168–o2169.
Go, M.-L., Wu, X. & Liu, X.-L. (2005). Curr. Med. Chem. 12, 483–499.
organic compounds
o2532
Fun et al.
doi:10.1107/S1600536809037933
Acta Cryst. (2009). E65, o2532–o2533
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
‡ Thomson Reuters ResearcherID: A-3561-2009.
§ Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson
Reuters ResearcherID: A-5085-2009.

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Ni, L., Meng, C. Q. & Sikorski, J. A. (2004). Expert Opin. Ther. Pat. 14, 1669–
1691.
Patil, P. S. & Dharmaprakash, S. M. (2008). Mater. Lett. 62, 451–453.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Suwunwong, T., Chantrapromma, S., Pakdeevanich, P. & Fun, H.-K. (2009).
Acta Cryst. E65, o1575–o1576.
organic compounds
Acta Cryst. (2009). E65, o2532–o2533Fun et al.
? C13H11NOS?0.5C2H6O
o2533

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supplementary materials

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supplementary materials
sup-1
Acta Cryst. (2009). E65, o2532-o2533 [ doi:10.1107/S1600536809037933 ]
(2E)-1-(4-Aminophenyl)-3-(2-thienyl)prop-2-en-1-one ethanol hemisolvate
H.-K. Fun, T. Kobkeatthawin and S. Chantrapromma
Comment
Chalcones have been reported to be responsible for a variety of biological activities such as analgesic, anti-inflammatory,
antibacterial and antimycotic properties (Dimmock et al., 1999; Go et al., 2005; Ni et al., 2004). Some of the synthetic
chalcones have also been found to be non-linear optical (NLO) materials (Patil & Dharmaprakash, 2008). These interesting
activities have led us to synthesize the title heteroaryl chalcone, (I), in order to study its NLO properties and biological
activities. Herein we report the crystal strcuture of (I). The title compound crystallizes in orthorhombic noncentrosymmetric
space group P212121 and therefore it is expected to exhibit second-order non-linear optic properties.
The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E configuration with respect to the C8═C9 double
bond [1.346 (3) Å], with C7—C8—C9—C10 torsion angle of 179.1 (2)°. The molecule is essentially planar as indicated
by the dihedral angle between thiophene (C10–C13/S1) and 4-aminophenyl rings of 3.1 (2)°. Bond distances (Allen et al.,
1987) and angles show normal values and are comparable with those observed in closely related structures (Fun et al., 2009;
Suwunwong et al., 2009).
In the crystal, molecules are linked into chains along the b axis through N—H···O hydrogen bonds (Fig. 2 and Table 1).
The chains are interlinked via N—H···π interactions (Table 1) involving the C10-C13/S1 ring (Fig.2).
Experimental
The title compound was synthesized by the condensation of 4-aminoacetophenone (0.40 g, 3 mmol) with thiophene-2-car-
boxaldehyde (0.28 ml, 3 mmol) in ethanol (30 ml) in the presence of 10% NaOH (aq) (5 ml). After stirring for 2 hr at room
temperature, the resulting yellow solid was collected by filtration, washed with distilled water, dried and purified by repeated
recrystallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determ-
ination were grown by slow evaporation of an ethanol solution at room temperature after several days, (m.p. 378–379 K).
Refinement
The thiophene ring of the chalcone is disordered over two orientations with occupancies of 0.842 (3) and 0.158 (3). The same
anisotropic displacement parameters were used for atoms pairs C12A/C11, C11A/C12 and C13A/C13. Atoms S1A, C11A,
C12A, C13A and C10 were restrained to be coplanar. The ethanol solvent molecule is also disordered over two positions
across a center of symmetry. Their occupanicies were initially refined to 0.248 (5) and 0.242 (5) and later both were fixed at
0.25. Both disorder components were refined isotropically. The C—O, C—C and O···C distances were restrained to 1.42 (1),
1.51 (1) and 2.43 (1) Å, respectively. All H atoms were placed in calculated positions, with N-H = 0.86 Å, C-H = 0.93-0.97
Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl and hydroxyl H atoms and 1.2Ueq(C) for
the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak
is located at 0.96 Å from H2B and the deepest hole is located at 0.30 Å from H14B. The final difference density features
indicate that the solvent molecule may be disordered over multiple sites.

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supplementary materials
sup-2
Figures
Fig. 1. The molecular structure of the title compound, showing 50% probability displacement
ellipsoids and the atom-numbering scheme. The minor disorder components are shown in
open bonds.
Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing chains
running along the b axis. N—H···O hydrogen bonds and N—H···π interactions are shown as
dashed lines. Only the major disorder component is shown. For clarity, the disordered ethanol
solvent molecules are not shown.
(2E)-1-(4-Aminophenyl)-3-(2-thienyl)prop-2-en-1-one ethanol hemisolvate
Crystal data
C13H11NOS·0.5C2H6O
Dx = 1.277 Mg m−3
Melting point = 378–379 K
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4225 reflections
θ = 1.8–31.1º
µ = 0.24 mm−1
T = 100 K
Mr = 252.32
Orthorhombic, P212121
Hall symbol: P 2ac 2ab
a = 5.1413 (1) Å
b = 13.9754 (2) Å
c = 18.2647 (2) Å
V = 1312.35 (3) Å3
Z = 4
F000 = 532
Plate, yellow
0.56 × 0.22 × 0.17 mm
Data collection
Bruker APEXII CCD area-detector
diffractometer
Radiation source: sealed tube
Monochromator: graphite
T = 100 K
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
Tmin = 0.879, Tmax = 0.961
22258 measured reflections
4225 independent reflections
3893 reflections with I > 2σ(I)
Rint = 0.026
θmax = 31.1º
θmin = 1.8º
h = −7→7
k = −20→15
l = −26→24
Refinement
Refinement on F2
Hydrogen site location: inferred from neighbouring
sites