(E)-4-(4-Eth­oxy­phen­yl)but-3-en-2-one

Kamalini, G.J.S.; Sugaraj, S.R.; Reuben Jonathan, D.; Revathi, B.K.; Usha, G.

doi:10.1107/S2414314616006106

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160610

doi:10.1107/S2414314616006106

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(E)-4-(4-Ethoxyphenyl)but-3-en-2-one

G. Joseline Sheeba Kamalini,^a Samuel R. Sugaraj,^b D. Reuben Jonathan,^c B. K. Revathi ^d and G. Usha ^d ^*

^aDepartment of Physics, St. Peter's University, Chennai 600 054, Tamilnadu, India, ^bDepartment of Physics, The New College, Chennai 600 014, Tamilnadu, India, ^cDepartment of Chemistry, Madras Christian College, Chennai-59, India, and ^dPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 30 March 2016; accepted 12 April 2016; online 22 April 2016)

In the title compound, C₁₂H₁₄O₂, the benzene ring makes dihedral angles of 5.03 (8) and 5.37 (15)° with the mean planes of the but-3-en-2-one group and the ethoxy group, respectively. In the crystal, molecules are linked by two pairs of C—H⋯O hydrogen bonds forming inversion dimers, which enclose an R₂²(8) ring motif flanked by two R₂¹(7) loops.

Keywords: crystal structure; chalcones; but-3-en-2-one; C—H⋯O hydrogen bonds; inversion dimers.

CCDC reference: 1452611

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Chemical scheme

Structure description

Chalcones belonging to the flavonoid family constitute an important group of natural products due to their unforeseen pharmacological potential. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. Chalcones have been reported to possess numerous biological activities such as antimicrobial, anti-inflammatory, antimalarial, antileishmanial, antioxidant and antitubercular activities (Lin et al., 2002 ; Sivakumar et al., 2007 ). The reactive α,β-unsaturated keto group in chalcone derivatives was observed to be responsible for their antimicrobial activity.

In the title compound, Fig. 1, both the but-3-en-2-one group and the ethoxy group are −antiperiplanar (−ap) with respect to the benzene ring, as indicated by the torsion angles C7—C6—C9—C10 = −179.84 (14)° and C7—C8—C3—O1 = −178.41 (13)°. The but-3-en-2-one group and the ethoxy group make dihedral angles of 5.03 (8) and 5.37 (15)°, respectively, with the benzene ring.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, molecules are linked by two pairs of C—H⋯O hydrogen bonds forming inversion dimers, which enclose an R₂²(8) ring motif flanked by two R₂¹(7) loops (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.93	2.50	3.4298 (17)	178
C10—H10⋯O2ⁱ	0.93	2.57	3.5006 (17)	179
Symmetry code: (i) -x, -y-1, -z.

Figure 2
The crystal packing of the title compound, viewed along the a axis. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

Synthesis and crystallization

In a 250 ml round-bottom flask acetone (0.5 mmol) and 4-ethoxybenzaldehyde (0.5 mmol) were taken and 120 ml of absolute alcohol was added. The mixture was stirred at room temperature for 5 min, then 10% sodium hydroxide solution was added and the mixture was stirred for 2 h. The yellow-coloured precipitate generated by adding a sufficient amount of ice-cold water was filtered, washed with distilled water and then dried. The crude product was recrystallized twice from absolute alcohol yielding colourless block-like crystals (yield 78%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₄O₂
M_r	190.23
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	5.7634 (2), 8.2218 (2), 12.0915 (3)
α, β, γ (°)	105.5413 (14), 102.5395 (16), 97.4291 (14)
V (Å³)	528.03 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	7360, 1858, 1589
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.121, 1.03
No. of reflections	1842
No. of parameters	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13
Computer programs: APEX2, SAINT and XPREP (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1452611

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616006106/su4027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006106/su4027Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006106/su4027Isup3.cml

checkCIF report

Experimental top

Structure description top

Chalcones belonging to the flavonoid family constitute an important group of natural products due to their unforeseen pharmacological potential. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. Chalcones have been reported to possess numerous biological activities such as antimicrobial, anti-inflammatory, antimalarial, antileishmanial, antioxidant and antitubercular activities (Lin et al., 2002; Sivakumar et al., 2007). The reactive α,β-unsaturated keto group in chalcone derivatives was observed to be responsible for their antimicrobial activity.

In the title compound, Fig. 1, both the but-3-en-2-one group and the ethoxy group are -antiperiplanar (-ap) with respect to the benzene ring, as indicated by the torsion angles C7—C6—C9—C10 = -179.84 (14)° and C7—C8—C3—O1 = -178.41 (13)°. The but-3-en-2-one group and the ethoxy group make dihedral angles of 5.03 (8) and 5.37 (15)°, respectively, with the benzene ring.

In the crystal, molecules are linked by two pairs of C—H···O hydrogen bonds forming inversion dimers, which enclose an R₂²(8) ring motif flanked by two R₂¹(7) loops (Table 1 and Fig. 2).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. The C—H···O hydrogen bonds are shown as dashed lines (see Table 1).

(E)-4-(4-Ethoxyphenyl)but-3-en-2-one top

Crystal data top

C₁₂H₁₄O₂	Z = 2
M_r = 190.23	F(000) = 204
Triclinic, P1	D_x = 1.196 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7634 (2) Å	Cell parameters from 1858 reflections
b = 8.2218 (2) Å	θ = 1.8–25.0°
c = 12.0915 (3) Å	µ = 0.08 mm⁻¹
α = 105.5413 (14)°	T = 296 K
β = 102.5395 (16)°	Block, colorless
γ = 97.4291 (14)°	0.30 × 0.25 × 0.25 mm
V = 528.03 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	1858 independent reflections
Radiation source: fine-focus sealed tube	1589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and φ scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
T_min = 0.976, T_max = 0.980	k = −9→9
7360 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0652P)² + 0.0923P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1842 reflections	Δρ_max = 0.17 e Å⁻³
130 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (7)

Crystal data top

C₁₂H₁₄O₂	γ = 97.4291 (14)°
M_r = 190.23	V = 528.03 (3) Å³
Triclinic, P1	Z = 2
a = 5.7634 (2) Å	Mo Kα radiation
b = 8.2218 (2) Å	µ = 0.08 mm⁻¹
c = 12.0915 (3) Å	T = 296 K
α = 105.5413 (14)°	0.30 × 0.25 × 0.25 mm
β = 102.5395 (16)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1858 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1589 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.020
7360 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
1842 reflections	Δρ_min = −0.13 e Å⁻³
130 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.0703 (4)	0.3733 (2)	0.64921 (17)	0.0787 (6)
H1A	1.1266	0.4691	0.6242	0.118*
H1B	1.2069	0.3329	0.6860	0.118*
H1C	0.9777	0.4089	0.7053	0.118*
C2	0.9134 (3)	0.2306 (2)	0.54296 (13)	0.0568 (4)
H2A	1.0055	0.1920	0.4860	0.068*
H2B	0.8529	0.1336	0.5671	0.068*
C3	0.5377 (3)	0.19381 (18)	0.39674 (12)	0.0474 (4)
C4	0.5370 (3)	0.02313 (18)	0.33933 (13)	0.0504 (4)
H4	0.6675	−0.0263	0.3639	0.060*
C5	0.3417 (3)	−0.07347 (17)	0.24538 (12)	0.0485 (4)
H5	0.3427	−0.1878	0.2076	0.058*
C6	0.1442 (2)	−0.00352 (17)	0.20622 (11)	0.0439 (3)
C7	0.1524 (3)	0.16901 (19)	0.26405 (13)	0.0526 (4)
H7	0.0239	0.2197	0.2389	0.063*
C8	0.3449 (3)	0.26628 (19)	0.35711 (13)	0.0552 (4)
H8	0.3457	0.3814	0.3937	0.066*
C9	−0.0692 (2)	−0.10142 (18)	0.10940 (12)	0.0458 (4)
H9	−0.1907	−0.0412	0.0912	0.055*
C10	−0.1105 (2)	−0.26480 (17)	0.04465 (12)	0.0476 (4)
H10	0.0082	−0.3277	0.0617	0.057*
C11	−0.3285 (3)	−0.35470 (17)	−0.05185 (12)	0.0468 (4)
C12	−0.5374 (3)	−0.26762 (19)	−0.07783 (14)	0.0553 (4)
H12A	−0.4946	−0.1819	−0.1143	0.083*
H12B	−0.5756	−0.2137	−0.0050	0.083*
H12C	−0.6759	−0.3514	−0.1308	0.083*
O1	0.71689 (19)	0.29938 (13)	0.49135 (9)	0.0613 (3)
O2	−0.3390 (2)	−0.50178 (14)	−0.11143 (10)	0.0720 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0714 (12)	0.0707 (12)	0.0673 (11)	−0.0023 (9)	−0.0184 (9)	0.0142 (9)
C2	0.0512 (9)	0.0588 (9)	0.0510 (8)	0.0044 (7)	0.0005 (7)	0.0147 (7)
C3	0.0465 (8)	0.0436 (8)	0.0425 (7)	0.0015 (6)	0.0051 (6)	0.0061 (6)
C4	0.0476 (8)	0.0454 (8)	0.0509 (8)	0.0119 (6)	0.0038 (6)	0.0090 (6)
C5	0.0524 (8)	0.0375 (7)	0.0469 (7)	0.0077 (6)	0.0066 (6)	0.0043 (6)
C6	0.0429 (7)	0.0427 (7)	0.0415 (7)	0.0052 (6)	0.0082 (6)	0.0089 (6)
C7	0.0472 (8)	0.0467 (8)	0.0545 (8)	0.0132 (6)	0.0038 (6)	0.0058 (6)
C8	0.0546 (9)	0.0416 (8)	0.0556 (8)	0.0102 (7)	0.0038 (7)	0.0005 (6)
C9	0.0427 (7)	0.0443 (8)	0.0462 (7)	0.0100 (6)	0.0064 (6)	0.0107 (6)
C10	0.0431 (8)	0.0443 (8)	0.0492 (8)	0.0109 (6)	0.0032 (6)	0.0104 (6)
C11	0.0471 (8)	0.0408 (8)	0.0455 (7)	0.0069 (6)	0.0040 (6)	0.0093 (6)
C12	0.0475 (8)	0.0515 (9)	0.0555 (8)	0.0108 (7)	0.0000 (6)	0.0080 (7)
O1	0.0563 (7)	0.0474 (6)	0.0569 (6)	0.0046 (5)	−0.0103 (5)	0.0007 (5)
O2	0.0704 (8)	0.0453 (6)	0.0747 (8)	0.0177 (5)	−0.0096 (6)	−0.0035 (5)

Geometric parameters (Å, º) top

C1—C2	1.502 (2)	C6—C7	1.393 (2)
C1—H1A	0.9600	C6—C9	1.4648 (19)
C1—H1B	0.9600	C7—C8	1.372 (2)
C1—H1C	0.9600	C7—H7	0.9300
C2—O1	1.4281 (18)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.322 (2)
C2—H2B	0.9700	C9—H9	0.9300
C3—O1	1.3608 (17)	C10—C11	1.4653 (19)
C3—C8	1.383 (2)	C10—H10	0.9300
C3—C4	1.388 (2)	C11—O2	1.2166 (17)
C4—C5	1.385 (2)	C11—C12	1.4966 (19)
C4—H4	0.9300	C12—H12A	0.9600
C5—C6	1.3897 (19)	C12—H12B	0.9600
C5—H5	0.9300	C12—H12C	0.9600

C2—C1—H1A	109.5	C7—C6—C9	119.14 (13)
C2—C1—H1B	109.5	C8—C7—C6	121.84 (14)
H1A—C1—H1B	109.5	C8—C7—H7	119.1
C2—C1—H1C	109.5	C6—C7—H7	119.1
H1A—C1—H1C	109.5	C7—C8—C3	120.25 (13)
H1B—C1—H1C	109.5	C7—C8—H8	119.9
O1—C2—C1	106.73 (13)	C3—C8—H8	119.9
O1—C2—H2A	110.4	C10—C9—C6	128.01 (13)
C1—C2—H2A	110.4	C10—C9—H9	116.0
O1—C2—H2B	110.4	C6—C9—H9	116.0
C1—C2—H2B	110.4	C9—C10—C11	125.16 (13)
H2A—C2—H2B	108.6	C9—C10—H10	117.4
O1—C3—C8	115.88 (13)	C11—C10—H10	117.4
O1—C3—C4	124.88 (13)	O2—C11—C10	119.43 (13)
C8—C3—C4	119.25 (13)	O2—C11—C12	119.80 (13)
C5—C4—C3	119.86 (13)	C10—C11—C12	120.77 (12)
C5—C4—H4	120.1	C11—C12—H12A	109.5
C3—C4—H4	120.1	C11—C12—H12B	109.5
C4—C5—C6	121.55 (13)	H12A—C12—H12B	109.5
C4—C5—H5	119.2	C11—C12—H12C	109.5
C6—C5—H5	119.2	H12A—C12—H12C	109.5
C5—C6—C7	117.24 (13)	H12B—C12—H12C	109.5
C5—C6—C9	123.62 (13)	C3—O1—C2	119.21 (12)

O1—C3—C4—C5	178.51 (13)	C4—C3—C8—C7	1.7 (2)
C8—C3—C4—C5	−1.6 (2)	C5—C6—C9—C10	−0.4 (2)
C3—C4—C5—C6	0.2 (2)	C7—C6—C9—C10	−179.84 (14)
C4—C5—C6—C7	1.1 (2)	C6—C9—C10—C11	−179.57 (12)
C4—C5—C6—C9	−178.37 (12)	C9—C10—C11—O2	174.48 (14)
C5—C6—C7—C8	−1.0 (2)	C9—C10—C11—C12	−5.5 (2)
C9—C6—C7—C8	178.49 (13)	C8—C3—O1—C2	175.46 (13)
C6—C7—C8—C3	−0.4 (2)	C4—C3—O1—C2	−4.6 (2)
O1—C3—C8—C7	−178.41 (13)	C1—C2—O1—C3	−176.21 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.50	3.4298 (17)	178
C10—H10···O2ⁱ	0.93	2.57	3.5006 (17)	179

Symmetry code: (i) −x, −y−1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.50	3.4298 (17)	178
C10—H10···O2ⁱ	0.93	2.57	3.5006 (17)	179

Symmetry code: (i) −x, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄O₂
M_r	190.23
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.7634 (2), 8.2218 (2), 12.0915 (3)
α, β, γ (°)	105.5413 (14), 102.5395 (16), 97.4291 (14)
V (Å³)	528.03 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	7360, 1858, 1589
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.121, 1.03
No. of reflections	1842
No. of parameters	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

The authors thank the Department of Chemistry, IIT, Madras, for use of the X-ray data collection facility.

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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