(E)-3-(4-Chloro-phen-yl)-1-(2-fur-yl)prop-2-en-1-one.

In the title mol-ecule, C(13)H(9)ClO(2), the benzene and furyl rings are slightly twisted from each other with a dihedral angle of 5.1 (1)°. An intra-molecular C-H⋯O hydrogen-bond inter-action generates an S(5) ring motif. In the crystal structure, mol-ecules are stacked along the b axis and the crystal packing is stabilized by weak inter-molecular 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 = 232.65

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.08

5209 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 2227 Friedel pairs

Flack parameter: 0.07 (6)

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 ▶).

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

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

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

C13H9ClO2	F000 = 480
Mr = 232.65	Dx = 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 = 2.5–37.2º
b = 3.79120 (10) Å	µ = 0.34 mm−1
c = 12.9444 (4) Å	T = 100.0 (1) K
V = 1047.25 (5) Å3	Block, colourless
Z = 4	0.40 × 0.29 × 0.21 mm

Bruker SMART APEXII CCD area-detector diffractometer	5209 independent reflections
Radiation source: fine-focus sealed tube	4211 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 100.0(1) K	θmax = 38.2º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −31→37
Tmin = 0.875, Tmax = 0.931	k = −6→6
13568 measured reflections	l = −22→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.58 e Å−3
5209 reflections	Δρmin = −0.27 e Å−3
145 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 2216 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (6)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .