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

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

doi:10.1107/S1600536808020965

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1467

doi:10.1107/S1600536808020965

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(E)-3-(2-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 3 July 2008; accepted 7 July 2008; online 12 July 2008)

The title compound, C₁₃H₉ClO₂, adopts an E configuration with respect to the C=C double bond of the propenone unit. The benzene and furyl rings are twisted slightly from each other, making a dihedral angle of 6.47 (7)°. Intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds generate an S(5)S(5)S(5) ring motif. In the crystal structure, molecules are stacked along the b axis and weak intermolecular C—H⋯O hydrogen bonds are observed.

Related literature

For related literature on chalcone derivatives, see: Patil et al. (2006 ); Patil, Ng et al. (2007 ); Patil, Fun et al. (2007 ). For bond-length data, see: Allen et al. (1987 ); Fun et al. (2008 ). 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 = 19.6826 (4) Å
b = 3.8395 (1) Å
c = 14.0491 (3) Å
V = 1061.71 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 100.0 (1) K
0.44 × 0.23 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.865, T_max = 0.952
30354 measured reflections
3902 independent reflections
3738 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.09
3902 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1881 Friedel pairs
Flack parameter: −0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.93	2.52	3.4126 (14)	161
C11—H11A⋯O2ⁱⁱ	0.93	2.55	3.1488 (17)	123
C7—H7A⋯Cl1	0.93	2.64	3.0675 (12)	108
C7—H7A⋯O2	0.93	2.50	2.8255 (14)	101
C8—H8A⋯O1	0.93	2.49	2.8249 (15)	101
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, -y-1, z-{\script{1\over 2}}]$ .

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/S1600536808020965/is2312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020965/is2312Isup2.hkl

checkCIF report

Comment top

The title compound, (I), whose structure is reported here, is a chalcone derivative that we have prepared; the crystal structures of some of these compounds have been studied previously (Patil et al., 2006; Patil, Ng et al., 2007; Patil, Fun et al., 2007).

In (I), the moleule exhibits an E configuration with respect to the C7═C8 double bond with the C6—C7—C8—C9 torsion angle being 178.45 (10)°. The bond lengths and bond angles in (I) are found to have normal values (Allen et al., 1987; Fun et al., 2008). The phenyl and furyl rings in the molecule is planar with the maximum deviation from planarity being 0.005 (13) Å for atom C6 and 0.004 (11) Å for atom O1, respectively. The dihedral angle between the phenyl and the furyl ring are 6.47 (7)°, indicating that they are slightly twisted from each other. The non-centrosymmmetric crystal of the title compound should exhibit 2nd-order NLO properties.

Intramolecular C—H···O and C—H···Cl hydrogen bonds generate an S(5)S(5)S(5) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are stacked along the b axis. The crystal packing is consolidated by inter and intramolecular C—H···O and C—H···Cl hydrogen bonding interactions.

Related literature top

For related literature on chalcone derivatives, see: Patil et al. (2006); Patil, Ng et al. (2007); Patil, Fun et al. (2007). For bond-length data, see: Allen et al. (1987); Fun et al. (2008). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The compound (I) was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol, 1.49 mg) 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. The 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. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₃H₉ClO₂	F(000) = 480
M_r = 232.65	D_x = 1.455 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9970 reflections
a = 19.6826 (4) Å	θ = 2.5–37.2°
b = 3.8395 (1) Å	µ = 0.34 mm⁻¹
c = 14.0491 (3) Å	T = 100 K
V = 1061.71 (4) Å³	Block, colourless
Z = 4	0.44 × 0.23 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3902 independent reflections
Radiation source: fine-focus sealed tube	3738 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 32.8°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −29→29
T_min = 0.865, T_max = 0.952	k = −5→5
30354 measured reflections	l = −21→21

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.06P)² + 0.0834P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
3902 reflections	Δρ_max = 0.42 e Å⁻³
145 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1881 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (4)

Crystal data top

C₁₃H₉ClO₂	V = 1061.71 (4) Å³
M_r = 232.65	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 19.6826 (4) Å	µ = 0.34 mm⁻¹
b = 3.8395 (1) Å	T = 100 K
c = 14.0491 (3) Å	0.44 × 0.23 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3902 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3738 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.952	R_int = 0.034
30354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.42 e Å⁻³
S = 1.10	Δρ_min = −0.19 e Å⁻³
3902 reflections	Absolute structure: Flack (1983), 1881 Friedel pairs
145 parameters	Absolute structure parameter: −0.01 (4)
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	0.717808 (15)	0.28404 (8)	0.54723 (2)	0.02583 (8)
O1	0.56257 (5)	−0.2638 (2)	0.10796 (7)	0.02292 (18)
O2	0.52989 (4)	−0.2045 (3)	0.35622 (8)	0.02328 (19)
C13	0.47093 (6)	−0.4899 (3)	0.17874 (10)	0.0209 (2)
H13A	0.4398	−0.5572	0.2251	0.025*
C1	0.75871 (6)	0.3597 (3)	0.43900 (8)	0.01692 (19)
C2	0.82334 (6)	0.5030 (3)	0.44283 (9)	0.0203 (2)
H2A	0.8429	0.5581	0.5012	0.024*
C3	0.85871 (6)	0.5636 (3)	0.35885 (10)	0.0205 (2)
H3A	0.9022	0.6575	0.3606	0.025*
C4	0.82839 (6)	0.4826 (3)	0.27213 (9)	0.0188 (2)
H4A	0.8516	0.5252	0.2157	0.023*
C5	0.76378 (6)	0.3389 (3)	0.26935 (8)	0.0173 (2)
H5A	0.7444	0.2862	0.2107	0.021*
C6	0.72688 (6)	0.2709 (3)	0.35301 (9)	0.01496 (19)
C7	0.65913 (5)	0.1151 (3)	0.35030 (8)	0.01663 (18)
H7A	0.6348	0.1105	0.4070	0.020*
C8	0.62901 (5)	−0.0215 (3)	0.27343 (8)	0.0177 (2)
H8A	0.6512	−0.0168	0.2150	0.021*
C9	0.56065 (6)	−0.1798 (3)	0.28067 (8)	0.01660 (19)
C10	0.53018 (6)	−0.3151 (3)	0.19325 (9)	0.0167 (2)
C11	0.52194 (7)	−0.4069 (4)	0.03974 (10)	0.0256 (2)
H11A	0.5316	−0.4062	−0.0251	0.031*
C12	0.46571 (7)	−0.5500 (4)	0.07910 (10)	0.0238 (2)
H12A	0.4307	−0.6644	0.0474	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02834 (15)	0.03521 (16)	0.01394 (11)	−0.00595 (11)	0.00082 (12)	0.00028 (14)
O1	0.0203 (4)	0.0318 (5)	0.0166 (4)	−0.0043 (3)	0.0011 (3)	−0.0022 (3)
O2	0.0198 (4)	0.0327 (5)	0.0174 (4)	−0.0050 (3)	0.0022 (3)	−0.0006 (4)
C13	0.0175 (5)	0.0221 (5)	0.0231 (5)	−0.0020 (4)	−0.0007 (4)	−0.0002 (4)
C1	0.0184 (5)	0.0190 (4)	0.0134 (4)	0.0011 (4)	−0.0005 (4)	0.0002 (4)
C2	0.0191 (5)	0.0228 (5)	0.0189 (5)	−0.0005 (4)	−0.0045 (4)	−0.0002 (4)
C3	0.0152 (4)	0.0215 (5)	0.0249 (5)	−0.0003 (4)	−0.0026 (4)	0.0012 (4)
C4	0.0169 (5)	0.0198 (5)	0.0196 (5)	0.0003 (4)	0.0013 (4)	0.0026 (4)
C5	0.0168 (5)	0.0191 (5)	0.0159 (5)	0.0005 (4)	−0.0001 (4)	0.0005 (4)
C6	0.0146 (4)	0.0153 (4)	0.0149 (5)	0.0013 (3)	−0.0011 (4)	0.0004 (4)
C7	0.0156 (4)	0.0183 (4)	0.0160 (4)	−0.0008 (3)	0.0001 (4)	0.0013 (4)
C8	0.0145 (4)	0.0211 (5)	0.0177 (5)	−0.0015 (4)	0.0005 (4)	−0.0010 (4)
C9	0.0151 (4)	0.0173 (4)	0.0174 (5)	0.0005 (3)	−0.0006 (4)	0.0000 (4)
C10	0.0162 (5)	0.0180 (5)	0.0160 (5)	0.0003 (3)	0.0010 (4)	−0.0005 (4)
C11	0.0267 (6)	0.0319 (6)	0.0182 (5)	−0.0006 (5)	−0.0020 (5)	−0.0040 (5)
C12	0.0221 (5)	0.0231 (5)	0.0263 (6)	−0.0013 (4)	−0.0063 (4)	−0.0036 (5)

Geometric parameters (Å, º) top

Cl1—C1	1.7449 (12)	C4—C5	1.3868 (16)
O1—C11	1.3637 (16)	C4—H4A	0.9300
O1—C10	1.3715 (15)	C5—C6	1.4061 (17)
O2—C9	1.2256 (15)	C5—H5A	0.9300
C13—C10	1.3610 (16)	C6—C7	1.4622 (16)
C13—C12	1.4224 (19)	C7—C8	1.3389 (16)
C13—H13A	0.9300	C7—H7A	0.9300
C1—C2	1.3869 (17)	C8—C9	1.4800 (15)
C1—C6	1.4030 (16)	C8—H8A	0.9300
C2—C3	1.3895 (18)	C9—C10	1.4621 (16)
C2—H2A	0.9300	C11—C12	1.3537 (19)
C3—C4	1.3918 (18)	C11—H11A	0.9300
C3—H3A	0.9300	C12—H12A	0.9300

C11—O1—C10	106.48 (10)	C1—C6—C7	121.95 (11)
C10—C13—C12	106.81 (11)	C5—C6—C7	121.69 (11)
C10—C13—H13A	126.6	C8—C7—C6	125.81 (11)
C12—C13—H13A	126.6	C8—C7—H7A	117.1
C2—C1—C6	122.63 (11)	C6—C7—H7A	117.1
C2—C1—Cl1	117.10 (9)	C7—C8—C9	120.53 (11)
C6—C1—Cl1	120.26 (9)	C7—C8—H8A	119.7
C1—C2—C3	119.54 (11)	C9—C8—H8A	119.7
C1—C2—H2A	120.2	O2—C9—C10	119.82 (10)
C3—C2—H2A	120.2	O2—C9—C8	122.72 (11)
C2—C3—C4	119.41 (10)	C10—C9—C8	117.46 (10)
C2—C3—H3A	120.3	C13—C10—O1	109.77 (11)
C4—C3—H3A	120.3	C13—C10—C9	130.74 (11)
C5—C4—C3	120.44 (11)	O1—C10—C9	119.49 (10)
C5—C4—H4A	119.8	C12—C11—O1	110.84 (12)
C3—C4—H4A	119.8	C12—C11—H11A	124.6
C4—C5—C6	121.60 (11)	O1—C11—H11A	124.6
C4—C5—H5A	119.2	C11—C12—C13	106.10 (11)
C6—C5—H5A	119.2	C11—C12—H12A	127.0
C1—C6—C5	116.36 (10)	C13—C12—H12A	127.0

C6—C1—C2—C3	0.14 (18)	C7—C8—C9—O2	−2.60 (17)
Cl1—C1—C2—C3	178.98 (9)	C7—C8—C9—C10	178.35 (11)
C1—C2—C3—C4	0.63 (17)	C12—C13—C10—O1	−0.30 (14)
C2—C3—C4—C5	−0.74 (18)	C12—C13—C10—C9	178.44 (12)
C3—C4—C5—C6	0.08 (18)	C11—O1—C10—C13	0.67 (14)
C2—C1—C6—C5	−0.76 (16)	C11—O1—C10—C9	−178.23 (11)
Cl1—C1—C6—C5	−179.57 (9)	O2—C9—C10—C13	−3.41 (19)
C2—C1—C6—C7	179.05 (11)	C8—C9—C10—C13	175.66 (12)
Cl1—C1—C6—C7	0.24 (15)	O2—C9—C10—O1	175.22 (11)
C4—C5—C6—C1	0.65 (16)	C8—C9—C10—O1	−5.70 (15)
C4—C5—C6—C7	−179.17 (10)	C10—O1—C11—C12	−0.80 (15)
C1—C6—C7—C8	−170.09 (11)	O1—C11—C12—C13	0.62 (15)
C5—C6—C7—C8	9.72 (17)	C10—C13—C12—C11	−0.19 (15)
C6—C7—C8—C9	178.45 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.93	2.52	3.4126 (14)	161
C11—H11A···O2ⁱⁱ	0.93	2.55	3.1488 (17)	123
C7—H7A···Cl1	0.93	2.64	3.0675 (12)	108
C7—H7A···O2	0.93	2.50	2.8255 (14)	101
C8—H8A···O1	0.93	2.49	2.8249 (15)	101

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+1, −y−1, 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)	19.6826 (4), 3.8395 (1), 14.0491 (3)
V (Å³)	1061.71 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.44 × 0.23 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.865, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	30354, 3902, 3738
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.762

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.10
No. of reflections	3902
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.19
Absolute structure	Flack (1983), 1881 Friedel pairs
Absolute structure parameter	−0.01 (4)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), 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
C3—H3A···O2ⁱ	0.93	2.52	3.4126 (14)	161.1
C11—H11A···O2ⁱⁱ	0.93	2.55	3.1488 (17)	122.9
C7—H7A···Cl1	0.93	2.64	3.0675 (12)	108.4
C7—H7A···O2	0.93	2.50	2.8255 (14)	101.0
C8—H8A···O1	0.93	2.49	2.8249 (15)	101.3

Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+1, −y−1, 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 Universiti Sains Malaysia for a post-doctoral 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

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. 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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Jebas, S. R., Razak, I. A., Patil, P. S., Dharmaprakash, S. M. & Deepak D'Silva, E. (2008). Acta Cryst. E64, o1177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497–o2498. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, P. S., Ng, S.-L., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o59–o60. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o896–o898. Web of Science CSD CrossRef IUCr Journals 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