(E)-1-(2-Amino­phen­yl)-3-(thio­phen-2-yl)prop-2-en-1-one

Suchada Chantrapromma; Pumsak Ruanwas; Nawong Boonnak; Hoong-Kun Fun

doi:10.1107/S1600536813014189

. 2013 Jun 8;69(Pt 7):o1004–o1005. doi: 10.1107/S1600536813014189

(E)-1-(2-Aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one

Suchada Chantrapromma ^a,^*,^‡, Pumsak Ruanwas ^a, Nawong Boonnak ^b, Hoong-Kun Fun ^c,^d,^§

PMCID: PMC3772449 PMID: 24046592

Abstract

The molecule of the title heteroaryl chalcone derivative, C₁₃H₁₁NOS, exists in a trans-configuaration and is almost planar with a dihedral angle of 3.73 (8)° between the phenyl and thiophene rings. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, two adjacent molecules are linked into a dimer in an anti-parallel face-to-face manner by a pair of C—H⋯O interactions. Neighboring dimers are further linked into chains along the c-axis direction by N—H⋯N hydrogen bonds.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Go et al. (2005 ▶); Liu et al. (2008 ▶); Molyneux (2004 ▶); Nerya et al. (2004 ▶); Ni et al. (2004 ▶); Shenvi et al. (2013 ▶); Suwunwong et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶). graphic file with name e-69-o1004-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₁NOS
M _r = 229.30
Monoclinic,
a = 24.9335 (4) Å
b = 5.0278 (1) Å
c = 18.6813 (3) Å
β = 111.151 (1)°
V = 2184.13 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.36 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.908, T _max = 0.984
14827 measured reflections
3942 independent reflections
2620 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.127
S = 1.04
3942 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014189/rz5065sup1.cif

e-69-o1004-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014189/rz5065Isup2.hkl

e-69-o1004-Isup2.hkl^{(193.3KB, hkl)}

Click here for additional data file.^{(4.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813014189/rz5065Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.83 (2)	1.97 (2)	2.6253 (18)	135.6 (19)
N1—H2N1⋯N1ⁱ	0.86 (2)	2.34 (2)	3.184 (2)	169 (2)
C11—H11A⋯O1ⁱⁱ	0.95	2.56	3.278 (2)	133

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0314/2552) is gratefully acknowledged. The authors extend their appreciation to Prince of Songkla University, the Deanship of Scientific Research at King Saud University and Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

supplementary crystallographic information

Comment

The basic structure of chalcones consists of two aromatic rings bound by an α,β-unsaturated carbonyl group, a unique template associated with various biological activities such as analgesic, anti-inflammatory, antibacterial (Go et al., 2005; Liu et al., 2008; Ni et al., 2004), anticancer and antioxidant (Shenvi et al., 2013) as well as tyrosinase inhibitory (Nerya et al., 2004) and fluorescence (Suwunwong et al., 2011) properties. The title compound (I) was synthesized and studied for antioxidant activity by the DPPH scavenging method (Molyneux, 2004). Our result showed that (I) exhibits a weakly antioxidant activity. It was also tested for antityrosinase activity but found to be inactive. Herein we report the crystal structure of (I).

The molecular structure of (I) exists in a trans configuration with respect to the C8═C9 double bond [1.340 (2)°] as indicated by the torsion angle C7–C8–C9–C10 = 179.29 (15)° (Fig. 1). The whole molecule is almost planar, the interplanar angle between phenyl and thiophene rings being 3.73 (8)° (Fig. 2). The propenone unit (C7—C9/O1) is almost planar with the torsion angle O1–C7–C8–C9 = -7.8 (2)°. The mean plane through the propenone bridge makes the dihedral angles of 7.37 (10) and 3.66 (10)° with the phenyl and thiophene rings, respectively. Intramolecular N1—H1N1···O1 hydrogen bond between amino and enone groups (Fig. 1 and Table 1) generates S(6) ring motif (Bernstein et al., 1995). This intramolecular hydrogen bond helps to stabilize the planarity of the structure. However it may result in the prohibition of the α,β-unsaturated carbonyl moiety to be reactive. The bond distances in (I) agree with the literature values (Allen et al., 1987) and are comparable with those observed in related structures (Fun et al., 2011; Suwunwong et al., 2009).

In the crystal packing (Fig. 3), two adjacent molecules are linked in an anti-parallel face-to-face manner into a dimer by a pair of C_thiophene—H···O interactions and the neighboring dimers are further linked into chains along the c axis by N—H···N hydrogen bonds (Fig. 4 and Table 1).

Experimental

The title compound (I) was prepared by mixing 2-aminoacetophenone (0.40 g, 3 mmol) and 2-thiophenecarboxaldehyde (0.34 g, 3 mmol) in ethanol (30 ml). 30% NaOH aqueous solution (5 ml) was then added and the mixture was stirred at room temperature for 2 hr. The yellow solid formed was filtered and washed with distilled water. Yellow block-shaped single crystals of (I) suitable for x-ray structure determination were recrystallized from ethanol by slow evaporation at room temperature over a few weeks. M.p. 407–408 K.