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

Fun, H.-K.; Patil, P.S.; Jebas, S.R.; Dharmaprakash, S.M.

doi:10.1107/S1600536808021934

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1530

doi:10.1107/S1600536808021934

Open

access

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

Hoong-Kun Fun,^a ^* P. S. Patil,^b Samuel Robinson Jebas ^a ‡ and S. M. Dharmaprakash ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 2 July 2008; accepted 14 July 2008; online 19 July 2008)

In the title molecule, C₁₃H₉ClO₂, the benzene and furyl rings are slightly twisted from each other with a dihedral angle of 5.1 (1)°. An intramolecular C—H⋯O hydrogen-bond interaction generates an S(5) ring motif. In the crystal structure, molecules are stacked along the b axis and the crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related literature on the biological and nonlinear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999 ); Chopra et al. (2007 ); DiCesare & Lakowicz (2000 ); Patil et al. (2006 , 2007 ); Gu, Ji, Patil & Dharmaprakash (2008 ); Gu, Ji, Patil, Dharmaprakash & Wang (2008 ). For bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₉ClO₂
M_r = 232.65
Orthorhombic, P n a 2₁
a = 21.3399 (7) Å
b = 3.7912 (1) Å
c = 12.9444 (4) Å
V = 1047.25 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 100.0 (1) K
0.40 × 0.29 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.875, T_max = 0.931
13568 measured reflections
5209 independent reflections
4211 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.08
5209 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 2227 Friedel pairs
Flack parameter: 0.07 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2	0.93	2.52	2.8411 (17)	101
C13—H13A⋯O2ⁱ	0.93	2.48	3.2535 (18)	140
Symmetry code: (i) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021934/lh2657sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021934/lh2657Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives continue to attract the interest of chemists, biologists and physicists due to their remarkable biological and nonlinear optical properties (Chopra et al., 2007; DiCesare & Lakowicz, 2000; Patil, et al., 2006, 2007; Agrinskaya et al., 1999; Gu, Ji, Patil & Dharmaprakash, 2008; Gu, Ji, Patil, Dharmaprakash & Wang, 2008). We have synthesized the title compound (I) and its structure is reported here.

The bond lengths and bond angles in (I) have normal values (Allen et al., 1987). The benzene and furyl rings in the molecule are essentially planar with the maximum deviation from planarity being -0.003 (18)Å for atom C12 and -0.004 (14)Å for atom O1 respectively. The dihedral angle between the benzene and the furyl rings is 5.1 (1)°, indicating that they are only slightly twisted from each other.

An intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are are stacked along the b axis. The crystal packing is consolidated by C—H···O hydrogen bond interactions.

Related literature top

For related literature on the biological and nonlinear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999); Chopra et al. (2007); DiCesare & Lakowicz (2000); Patil et al. (2006, 2007); Gu, Ji, Patil & Dharmaprakash (2008); Gu, Ji, Patil, Dharmaprakash & Wang (2008). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The compound (I) was synthesized by the condensation of 4 -chlorobenzaldehyde (0.01 mol, 1.49 g m) with 2-acetylfuran (0.01 mol, 1.01 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. Then precipitated compound was recrystallized from N, N-dimethylformamide (DMF).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₃H₉ClO₂	F(000) = 480
M_r = 232.65	D_x = 1.476 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4886 reflections
a = 21.3399 (7) Å	θ = 2.5–37.2°
b = 3.7912 (1) Å	µ = 0.34 mm⁻¹
c = 12.9444 (4) Å	T = 100 K
V = 1047.25 (5) Å³	Block, colourless
Z = 4	0.40 × 0.29 × 0.21 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5209 independent reflections
Radiation source: fine-focus sealed tube	4211 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 38.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −31→37
T_min = 0.875, T_max = 0.931	k = −6→6
13568 measured reflections	l = −22→19

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0686P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5209 reflections	Δρ_max = 0.58 e Å⁻³
145 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2216 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (6)

Crystal data top

C₁₃H₉ClO₂	V = 1047.25 (5) Å³
M_r = 232.65	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 21.3399 (7) Å	µ = 0.34 mm⁻¹
b = 3.7912 (1) Å	T = 100 K
c = 12.9444 (4) Å	0.40 × 0.29 × 0.21 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5209 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4211 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.931	R_int = 0.025
13568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.126	Δρ_max = 0.58 e Å⁻³
S = 1.08	Δρ_min = −0.28 e Å⁻³
5209 reflections	Absolute structure: Flack (1983), 2216 Friedel pairs
145 parameters	Absolute structure parameter: 0.07 (6)
1 restraint

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl1	0.249271 (17)	0.53749 (9)	0.21078 (5)	0.02637 (9)
O1	0.03179 (5)	0.2805 (3)	0.94149 (7)	0.0225 (2)
O2	0.00152 (6)	0.1062 (3)	0.74067 (9)	0.0266 (2)
C1	0.06091 (7)	0.3896 (4)	1.02879 (11)	0.0246 (3)
H1A	0.0454	0.3557	1.0952	0.030*
C2	0.11562 (8)	0.5548 (4)	1.00653 (12)	0.0243 (3)
H2A	0.1437	0.6536	1.0533	0.029*
C3	0.12135 (7)	0.5463 (4)	0.89712 (12)	0.0215 (3)
H3A	0.1540	0.6388	0.8581	0.026*
C4	0.06937 (7)	0.3752 (4)	0.86037 (10)	0.0192 (2)
C5	0.04991 (6)	0.2723 (4)	0.75621 (9)	0.0198 (2)
C6	0.09349 (7)	0.3737 (4)	0.67253 (10)	0.0202 (2)
H6A	0.1274	0.5190	0.6875	0.024*
C7	0.08493 (6)	0.2600 (4)	0.57564 (10)	0.0188 (2)
H7A	0.0496	0.1223	0.5633	0.023*
C8	0.12568 (6)	0.3314 (4)	0.48732 (9)	0.0178 (2)
C9	0.18485 (6)	0.4918 (4)	0.49906 (11)	0.0188 (2)
H9A	0.1984	0.5579	0.5645	0.023*
C10	0.22299 (7)	0.5524 (4)	0.41438 (11)	0.0192 (2)
H10A	0.2621	0.6577	0.4223	0.023*
C11	0.20160 (7)	0.4524 (4)	0.31741 (11)	0.0186 (2)
C12	0.14356 (7)	0.2960 (4)	0.30286 (10)	0.0198 (2)
H12A	0.1301	0.2333	0.2370	0.024*
C13	0.10594 (6)	0.2350 (4)	0.38834 (9)	0.0185 (2)
H13A	0.0670	0.1284	0.3797	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02847 (16)	0.02869 (17)	0.02196 (14)	−0.00201 (13)	0.00812 (11)	0.00173 (17)
O1	0.0200 (4)	0.0321 (6)	0.0156 (4)	0.0000 (4)	0.0017 (3)	0.0021 (4)
O2	0.0241 (5)	0.0361 (6)	0.0196 (4)	−0.0065 (4)	0.0001 (4)	0.0017 (4)
C1	0.0265 (7)	0.0314 (8)	0.0161 (5)	0.0055 (6)	−0.0005 (5)	−0.0023 (5)
C2	0.0268 (7)	0.0249 (7)	0.0211 (6)	0.0033 (5)	−0.0045 (5)	−0.0027 (5)
C3	0.0201 (6)	0.0220 (7)	0.0223 (6)	0.0000 (5)	−0.0018 (5)	0.0026 (5)
C4	0.0201 (5)	0.0218 (6)	0.0157 (5)	0.0029 (5)	0.0008 (4)	0.0019 (4)
C5	0.0204 (6)	0.0236 (6)	0.0153 (5)	0.0028 (5)	0.0010 (4)	0.0013 (4)
C6	0.0196 (5)	0.0224 (6)	0.0185 (5)	−0.0008 (5)	0.0010 (4)	0.0006 (5)
C7	0.0186 (5)	0.0197 (6)	0.0181 (5)	−0.0006 (5)	0.0004 (4)	0.0011 (4)
C8	0.0171 (5)	0.0209 (6)	0.0153 (5)	0.0020 (5)	−0.0006 (4)	−0.0002 (4)
C9	0.0191 (5)	0.0212 (6)	0.0160 (5)	0.0004 (5)	−0.0007 (4)	−0.0011 (4)
C10	0.0181 (6)	0.0187 (6)	0.0208 (5)	−0.0012 (5)	−0.0005 (4)	0.0003 (5)
C11	0.0209 (6)	0.0166 (6)	0.0185 (5)	0.0013 (5)	0.0031 (4)	0.0016 (4)
C12	0.0217 (6)	0.0212 (6)	0.0164 (5)	−0.0006 (5)	−0.0006 (4)	−0.0014 (4)
C13	0.0173 (5)	0.0218 (6)	0.0164 (5)	−0.0001 (5)	−0.0023 (4)	0.0004 (4)

Geometric parameters (Å, º) top

Cl1—C11	1.7446 (14)	C6—H6A	0.9300
O1—C1	1.3543 (18)	C7—C8	1.4617 (18)
O1—C4	1.3691 (16)	C7—H7A	0.9300
O2—C5	1.2261 (18)	C8—C13	1.3974 (17)
C1—C2	1.356 (2)	C8—C9	1.410 (2)
C1—H1A	0.9300	C9—C10	1.384 (2)
C2—C3	1.422 (2)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.388 (2)
C3—C4	1.370 (2)	C10—H10A	0.9300
C3—H3A	0.9300	C11—C12	1.386 (2)
C4—C5	1.4637 (18)	C12—C13	1.3865 (18)
C5—C6	1.4786 (18)	C12—H12A	0.9300
C6—C7	1.3388 (18)	C13—H13A	0.9300

C1—O1—C4	106.93 (11)	C6—C7—H7A	116.9
O1—C1—C2	111.03 (13)	C8—C7—H7A	116.9
O1—C1—H1A	124.5	C13—C8—C9	118.80 (12)
C2—C1—H1A	124.5	C13—C8—C7	119.30 (12)
C1—C2—C3	105.97 (14)	C9—C8—C7	121.90 (11)
C1—C2—H2A	127.0	C10—C9—C8	120.85 (12)
C3—C2—H2A	127.0	C10—C9—H9A	119.6
C4—C3—C2	106.68 (14)	C8—C9—H9A	119.6
C4—C3—H3A	126.7	C9—C10—C11	118.51 (12)
C2—C3—H3A	126.7	C9—C10—H10A	120.7
O1—C4—C3	109.39 (12)	C11—C10—H10A	120.7
O1—C4—C5	118.06 (12)	C12—C11—C10	122.24 (12)
C3—C4—C5	132.51 (13)	C12—C11—Cl1	119.52 (11)
O2—C5—C4	121.81 (12)	C10—C11—Cl1	118.23 (11)
O2—C5—C6	122.90 (13)	C11—C12—C13	118.71 (12)
C4—C5—C6	115.27 (12)	C11—C12—H12A	120.6
C7—C6—C5	121.11 (13)	C13—C12—H12A	120.6
C7—C6—H6A	119.4	C12—C13—C8	120.89 (12)
C5—C6—H6A	119.4	C12—C13—H13A	119.6
C6—C7—C8	126.29 (13)	C8—C13—H13A	119.6

C4—O1—C1—C2	0.69 (17)	C5—C6—C7—C8	−177.75 (13)
O1—C1—C2—C3	−0.41 (18)	C6—C7—C8—C13	−171.24 (14)
C1—C2—C3—C4	−0.02 (18)	C6—C7—C8—C9	9.4 (2)
C1—O1—C4—C3	−0.69 (16)	C13—C8—C9—C10	−0.2 (2)
C1—O1—C4—C5	177.19 (12)	C7—C8—C9—C10	179.11 (14)
C2—C3—C4—O1	0.44 (17)	C8—C9—C10—C11	0.2 (2)
C2—C3—C4—C5	−177.02 (15)	C9—C10—C11—C12	0.2 (2)
O1—C4—C5—O2	0.0 (2)	C9—C10—C11—Cl1	178.75 (11)
C3—C4—C5—O2	177.28 (16)	C10—C11—C12—C13	−0.6 (2)
O1—C4—C5—C6	−178.30 (12)	Cl1—C11—C12—C13	−179.09 (11)
C3—C4—C5—C6	−1.0 (2)	C11—C12—C13—C8	0.5 (2)
O2—C5—C6—C7	−6.2 (2)	C9—C8—C13—C12	−0.2 (2)
C4—C5—C6—C7	172.11 (14)	C7—C8—C13—C12	−179.49 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2	0.93	2.52	2.8411 (17)	101
C13—H13A···O2ⁱ	0.93	2.48	3.2535 (18)	140

Symmetry code: (i) −x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClO₂
M_r	232.65
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	21.3399 (7), 3.7912 (1), 12.9444 (4)
V (Å³)	1047.25 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.40 × 0.29 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.875, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	13568, 5209, 4211
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.870

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.08
No. of reflections	5209
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.28
Absolute structure	Flack (1983), 2216 Friedel pairs
Absolute structure parameter	0.07 (6)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2	0.93	2.52	2.8411 (17)	100.8
C13—H13A···O2ⁱ	0.93	2.48	3.2535 (18)	140.2

Symmetry code: (i) −x, −y, z−1/2.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

References

Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914–1917. Web of Science CrossRef CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chopra, D., Mohan, T. P., Vishalakshi, B. & Guru Row, T. N. (2007). Acta Cryst. C63, o704–o710. Web of Science CSD CrossRef IUCr Journals Google Scholar
DiCesare, N. & Lakowicz, J. R. (2000). Tetrahedron Lett. 43, 2615–2618. Web of Science CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gu, B., Ji, W., Patil, P. S. & Dharmaprakash, S. M. (2008). J. Appl. Phys. 103, 103511. Web of Science CrossRef Google Scholar
Gu, B., Ji, W., Patil, P. S., Dharmaprakash, S. M. & Wang, H. T. (2008). Appl. Phys. Lett. 92, 091118. Web of Science CrossRef Google Scholar
Patil, P. S., Dharmaprakash, S. M., Fun, H.-K. & Karthikeyan, M. S. (2006). J. Cryst. Growth, 297, 111–116. Web of Science CrossRef CAS Google Scholar
Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar