(E)-3-(3-Chloro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Naveed Ahmad; Hamid Latif Siddiqui; Muhammad Zia-ur-Rehman; Masood Parvez

doi:10.1107/S1600536810017150

. 2010 May 15;66(Pt 6):o1346–o1347. doi: 10.1107/S1600536810017150

(E)-3-(3-Chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Naveed Ahmad ^a, Hamid Latif Siddiqui ^a, Muhammad Zia-ur-Rehman ^b,^*, Masood Parvez ^c

PMCID: PMC2979640 PMID: 21579435

Abstract

The title molecule, C₁₆H₁₃ClO₂, is trans with respect to the C=C double bond. The dihedral angles between the mean plane of the prop-2-en-1-one unit and those of the 3-chloro- and 4-methoxy-substituted benzene rings are 20.93 (9) and 20.42 (10)°, respectively, and the dihedral angle between the mean planes of the two benzene rings is 40.96 (5)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Opletalova & Sedivy (1999 ▶); Lin et al. (2002 ▶); Nowakowska (2007 ▶). For the synthesis and biological activity of related chalcone derivatives, see: Hussain et al. (2009 ▶). For non-linear optical studies of chalcones, see: Sarojini et al. (2006 ▶); Poornesh et al. (2009 ▶); Shettigar et al. (2006 ▶; 2008 ▶). For related structures, see: Rosli et al. (2006 ▶); Patil et al. (2006 ▶); Harrison et al. (2006 ▶); Fun et al. (2008 ▶); Jasinski et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₃ClO₂
M _r = 272.71
Monoclinic,
a = 10.3415 (6) Å
b = 3.8938 (1) Å
c = 16.9152 (10) Å
β = 107.582 (2)°
V = 649.32 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 K
0.18 × 0.16 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.950, T _max = 0.989
2099 measured reflections
2099 independent reflections
2075 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.073
S = 1.15
2099 reflections
173 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ▶), 687 Friedel pairs
Flack parameter: 0.08 (6)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017150/lh5044sup1.cif

e-66-o1346-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017150/lh5044Isup2.hkl

e-66-o1346-Isup2.hkl^{(101.1KB, hkl)}

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
C7—H7A⋯O2ⁱ	0.98	2.58	3.545 (2)	168
C16—H16⋯O1ⁱⁱ	0.95	2.51	3.424 (2)	162

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

Acknowledgments

The authors are grateful to the Institute of Chemistry, University of the Punjab, Lahore, and the PCSIR Laboratories Complex, Lahore, for the provision of necessary facilities.

supplementary crystallographic information

Comment

Chalcones are well known for their biological activities (Dimmock et al., 1999). These have been reported as potential anti-fungal chemotherapeutic (Opletalova & Sedivy, 1999), anti-tuberculosis (Lin et al., 2002) and anti-infective & anti-inflammatory agents (Nowakowska, 2007). In addition, few among these have found their use as organic non-linear optical materials (NLO) due to their good SHG (second-harmonic generation) conversion efficiencies (Sarojini et al., 2006; Poornesh et al., 2009; Shettigar et al., 2006; 2008). In continuation of our work on chalcones (Hussain et al., 2009) and in view of the importance of chloro chalcones, the synthesis and crystal structure of the title compound, (I), is presented in this article.

The title molecule (Fig. 1) exhibits an E configuration with respect to the C═C double bond, the torsion angle C–C═C–C being -177.75 (17)°. The dihedral angle between the mean planes of the 3-chloro and 4-methoxy substituted benzene rings is 40.96 (5)°. The dihedral angles between the mean planes of the prop-2-en-1-one unit and those of the 3-chloro and 4-methoxy substitued benzene rings are 20.93 (9) and 20.42 (10)°, respectively. The geometrical parameters for (I) are consistent with those of some recently reported chalcone derivatives closely related to (I) (Rosli et al., 2006; Patil et al., 2006; Harrison et al., 2006; Fun et al.; 2008; Jasinski et al., 2010). The structure is stabilized by intermolecular interactions of the type C—H···O resulting in polymeric chains along the b-axis (Fig. 2, Tab. 1)

Experimental

A mixture of 3-chlorobenzaldehyde (0.01 moles, 1.13 g), 4-methoxyacetophenone (0.01 moles, 1.37 ml) and sodium hydroxide solution (10%, 30 ml) was stirred at room temperature for 6 hrs. Precipitates obtained were poured into ice-cold water (500 ml) and left to stand for 2 hours followed by filtration of the resultant solid which was dried and crystallized from ethanol by slow evaporation.