(2E)-1-(2,4-Dichloro­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Tze Shyang Chia; M Sapnakumari; B Narayana; B K Sarojini

doi:10.1107/S1600536812016339

. 2012 Apr 21;68(Pt 5):o1465. doi: 10.1107/S1600536812016339

(2E)-1-(2,4-Dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, M Sapnakumari ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3344577 PMID: 22590339

Abstract

In the title compound, C₁₈H₁₆Cl₂O₄, the dihedral angle between the benzene rings is 82.40 (4)°. The methoxy groups at both meta positions of the 3,4,5-trimethoxyphenyl ring are slightly twisted from the aromatic ring [C—O—C—C = −166.60 (8) and −6.18 (13)°], whereas the methoxy group at the para position is almost perpendicular [C—O—C—C = 112.08 (9)°]. The ketone O atom is connected to the 2,4-dichlorophenyl group through a C_ar—C_ar—C—O (ar = aromatic) torsion angle of −116.43 (9)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into infinite chains along the b axis. The crystal structure also features C—H⋯π interactions.

Related literature

For a related structure, see: Fun et al. (2012 ▶). For background to various chalcone derivatives, see: Samshuddin et al. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₆Cl₂O₄
M _r = 367.21
Orthorhombic,
a = 9.4305 (5) Å
b = 13.9334 (8) Å
c = 25.6417 (14) Å
V = 3369.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 100 K
0.48 × 0.39 × 0.22 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.829, T _max = 0.917
24763 measured reflections
6139 independent reflections
5445 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.086
S = 1.03
6139 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.52 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/S1600536812016339/hb6742sup1.cif

e-68-o1465-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016339/hb6742Isup2.hkl

e-68-o1465-Isup2.hkl^{(300.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016339/hb6742Isup3.cml

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

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

Cg1 is the centroid of the C10—C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O3ⁱ	0.93	2.53	3.3442 (11)	147
C17—H17A⋯Cg1ⁱⁱ	0.96	2.60	3.2965 (11)	130

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. BN thanks the UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

supplementary crystallographic information

Comment

In continuation of our work on the synthesis of chalcones (Fun et al., 2012, Samshuddin et al., 2011) as potential precursors for biodynamic functionalized derivatives, the title compound was prepared and its crystal structure is now reported.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings (C1–C6 & C10–C15) is 82.40 (4)°. The two methoxy groups at both meta positions (at atoms C12 & C14) are slightly twisted from the attached benzene ring with torsion angles C16—O1—C12—C13 = -166.60 (8)° and C18—O3—C14—C15 = -6.18 (13)°, whereas the methoxy group at para position (at atom C13) is almost perpendicular with C17—O2—C13—C14 = 112.08 (9)°. The atom O4 is connected to 2,4-dichlorophenyl group (Cl1/Cl2/C1–C6) through torsion angle [C5—C6—C7—O4] of -116.43 (9)°. Bond lengths and angles are comparable to a related structure (Fun et al., 2012).

In the crystal (Fig. 2), molecules are linked by C9—H9A—O3 hydrogen bonds into infinite chains along the b axis. The crystal is further stabilized by C—H···π interactions (Table 1), involving Cg1 which is the centroid of C10—C15 ring.

Experimental

To a mixture of 2,4-dichloroacetophenone (1.89 g, 0.01 mol) and 3,4,5-trimethoxybenzaldehyde (1.96 g, 0.01 mol) in ethanol (50 ml), 15 ml of 10% sodium hydroxide solution was added and stirred at 0–5 °C for 1 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless blocks were grown from toluene as solvent by slow evaporation method (M.P.: 335–337 K).