(2E)-1-(2,5-Dimeth­oxy­phen­yl)-3-(3-nitro­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Tze Shyang Chia; B Narayana; Prakash S Nayak; B K Sarojini

doi:10.1107/S1600536811043224

. 2011 Oct 29;67(Pt 11):o3058–o3059. doi: 10.1107/S1600536811043224

(2E)-1-(2,5-Dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, B Narayana ^b, Prakash S Nayak ^b, B K Sarojini ^c

PMCID: PMC3247450 PMID: 22220068

Abstract

In the title compound, C₁₇H₁₅NO₅, an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The benzene rings form a dihedral angle of 6.45 (7)° with each other. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R ₂ ²(8) loops. Adjacent dimers are further connected by C—H⋯O hydrogen bonds into an infinite chain along the [011] direction.

Related literature

For biological activities of chalcones, see: Dimmock et al. (1999 ▶). For the structures of chalcone derivatives, see: Samshuddin et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011a ▶,b ▶). For related crystal structures, see: Jasinski et al. (2008 ▶); Sarojini et al. (2007 ▶); Ma (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₅NO₅
M _r = 313.30
Triclinic,
a = 7.5015 (5) Å
b = 7.9962 (5) Å
c = 13.2468 (8) Å
α = 86.507 (1)°
β = 80.342 (1)°
γ = 76.332 (1)°
V = 760.96 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.41 × 0.38 × 0.13 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.987
16631 measured reflections
4381 independent reflections
3195 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.179
S = 1.02
4381 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043224/is2794sup1.cif

e-67-o3058-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043224/is2794Isup2.hkl

e-67-o3058-Isup2.hkl^{(214.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043224/is2794Isup3.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
C3—H3A⋯O2ⁱ	0.93	2.55	3.4773 (18)	172
C8—H8A⋯O1	0.93	2.12	2.7727 (16)	126
C17—H17A⋯O5ⁱⁱ	0.96	2.50	3.309 (2)	142

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under a Research University Grant (No. 1001/PSKBP/8630013). BN thanks UGC-New Delhi, Government of India, for financial assistance for the purchase of chemicals through a BSR one-off grant.

supplementary crystallographic information

Comment

Chalcones can be easily obtained from the Claisen–Schmidt reaction of aromatic aldehydes and aromatic ketones. Chalcones have been reported to possess many useful properties including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumour and anticancer activities (Dimmock et al., 1999). The basic skeleton of chalcones which possess the α,β-unsaturated carbonyl group is a useful synthone for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; Fun et al., 2010a,b; Jasinski et al., 2010; Baktır et al., 2011a,b). The crystal structures of some related chalcones which contain the nitro and methoxy groups viz: (2E)-3-(4-methylphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Jasinski et al., 2008), (2E)-3-(2-chlorophenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007) and (E)-3-(4-methoxyphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Ma, 2007) have been reported. In view of the importance of chalcones, the crystal structure of the title compound is reported here.

The molecular structure of the title compound is shown in Fig. 1. The benzene rings (C1–C6 and C10–C15) make a dihedral angle of 6.45 (7)° with each other. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Jasinski et al., 2008; Sarojini et al., 2007; Ma, 2007). The molecular structure is stabilized by an intramolecular C8—H8A···O1 hydrogen bond (Table 1) which generates an S(6) ring motif (Fig. 1; Bernstein et al., 1995).

In the crystal structure (Fig. 2), the molecules are interconnected by C3—H3A···O2 hydrogen bonds (Table 1), forming a dimer with an R₂²(8) ring motif. These dimers are further linked by intermolecular C17—H17A···O5 hydrogen bonds into an infinite chains along the [011] direction.

Experimental

To a mixture of 2,5-dimethoxy acetophenone (1.5 ml, 0.01 mol) and 3-nitrobenzaldehyde (1.51 g, 0.01 mol) in ethanol (50 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10 °C for 3 h. The precipitate formed was collected by filtration and then purified by recrystallization from ethanol. The single crystals were grown from a DMF solution by slow evaporation method (m.p. 377–379 K).