1-(1-Benzofuran-2-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one.

In the title compound, C(17)H(11)ClO(2), the benzofuran ring system is almost planar (r.m.s. deviation = 0.011 Å) and forms a dihedral angle of 10.53 (6)° with the chloro-phenyl ring. No significant inter-molecular inter-actions are observed.

Related literature

For general background to chalcone, see: Dhar (1981 ▶). For the biological properties of benzofuran derivatives, see: Nasef et al. (1992 ▶); Bogolyubsakaya & Perovich (1964 ▶); Deshmukh et al. (2004 ▶); Stanislav et al. (2000 ▶); Brady et al. (1973 ▶); Kamal et al. (2006 ▶); Alejandro et al. (2008 ▶); Rajesh et al. (2006 ▶). For related structures, see: Devarajegowda et al. (2001 ▶); Kant et al. (2009 ▶).

Experimental

Crystal data

C17H11ClO2

M = 282.71

Monoclinic,

a = 15.9034 (12) Å

b = 14.1393 (12) Å

c = 5.9572 (5) Å

β = 93.039 (4)°

V = 1337.67 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.22 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.940, T max = 0.972

12871 measured reflections

3323 independent reflections

2665 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.02

3323 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003004/ci5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003004/ci5024Isup2.hkl

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

C17H11ClO2	F(000) = 584
Mr = 282.71	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Melting point: 398 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.9034 (12) Å	Cell parameters from 3323 reflections
b = 14.1393 (12) Å	θ = 1.3–28.4°
c = 5.9572 (5) Å	µ = 0.28 mm−1
β = 93.039 (4)°	T = 293 K
V = 1337.67 (19) Å3	Plate, white
Z = 4	0.22 × 0.20 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3323 independent reflections
Radiation source: fine-focus sealed tube	2665 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −21→20
Tmin = 0.940, Tmax = 0.972	k = −18→18
12871 measured reflections	l = −7→7

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.3221P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3323 reflections	Δρmax = 0.21 e Å−3
182 parameters	Δρmin = −0.24 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: 0.0117 (16)

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.

	x	y	z	Uiso*/Ueq
C1	1.22464 (9)	0.64723 (11)	0.5466 (3)	0.0508 (4)
H1	1.1909	0.6671	0.4232	0.061*
C2	1.31402 (10)	0.64001 (11)	0.5583 (2)	0.0497 (3)
C3	1.37837 (12)	0.65858 (13)	0.4117 (3)	0.0628 (4)
H3	1.3660	0.6820	0.2679	0.075*
C4	1.45972 (12)	0.64125 (15)	0.4865 (3)	0.0717 (5)
H4	1.5031	0.6535	0.3920	0.086*
C5	1.47890 (11)	0.60577 (15)	0.7004 (3)	0.0692 (5)
H5	1.5349	0.5939	0.7447	0.083*
C6	1.41797 (10)	0.58781 (13)	0.8476 (3)	0.0595 (4)
H6	1.4311	0.5644	0.9911	0.071*
C7	1.33559 (9)	0.60625 (11)	0.7727 (2)	0.0485 (3)
C8	1.19823 (9)	0.62016 (11)	0.7456 (3)	0.0517 (4)
C9	1.11355 (10)	0.61170 (12)	0.8310 (3)	0.0540 (4)
C10	1.04368 (10)	0.62421 (13)	0.6625 (3)	0.0560 (4)
H10	1.0546	0.6508	0.5242	0.067*
C11	0.96572 (9)	0.59891 (11)	0.7013 (3)	0.0493 (3)
H11	0.9572	0.5719	0.8407	0.059*
C12	0.89149 (8)	0.60906 (10)	0.5471 (2)	0.0440 (3)
C13	0.81273 (9)	0.58296 (11)	0.6193 (2)	0.0480 (3)
H13	0.8090	0.5549	0.7596	0.058*
C14	0.74015 (9)	0.59803 (11)	0.4862 (3)	0.0501 (3)
H14	0.6879	0.5812	0.5368	0.060*
C15	0.74645 (9)	0.63839 (11)	0.2773 (2)	0.0473 (3)
C16	0.82376 (9)	0.66272 (11)	0.1978 (2)	0.0493 (3)
H16	0.8271	0.6888	0.0553	0.059*
C17	0.89576 (9)	0.64786 (11)	0.3322 (2)	0.0489 (3)
H17	0.9479	0.6638	0.2792	0.059*
O1	1.26490 (6)	0.59456 (8)	0.89122 (17)	0.0552 (3)
O2	1.10294 (8)	0.59470 (11)	1.0286 (2)	0.0755 (4)
Cl1	0.65624 (3)	0.66004 (4)	0.10847 (8)	0.06940 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0515 (8)	0.0488 (8)	0.0506 (8)	0.0031 (6)	−0.0110 (6)	0.0007 (6)
C2	0.0542 (8)	0.0455 (8)	0.0481 (8)	0.0008 (6)	−0.0081 (6)	−0.0025 (6)
C3	0.0775 (11)	0.0621 (10)	0.0489 (8)	0.0026 (8)	0.0042 (8)	0.0027 (7)
C4	0.0633 (11)	0.0824 (13)	0.0706 (11)	−0.0021 (9)	0.0149 (9)	−0.0053 (10)
C5	0.0491 (8)	0.0854 (13)	0.0723 (11)	0.0035 (8)	−0.0041 (8)	−0.0112 (10)
C6	0.0537 (8)	0.0719 (11)	0.0515 (8)	0.0067 (8)	−0.0108 (7)	−0.0022 (8)
C7	0.0486 (7)	0.0495 (8)	0.0466 (7)	−0.0014 (6)	−0.0050 (6)	−0.0008 (6)
C8	0.0480 (7)	0.0488 (8)	0.0567 (8)	0.0013 (6)	−0.0114 (6)	−0.0001 (7)
C9	0.0519 (8)	0.0550 (9)	0.0541 (9)	−0.0010 (7)	−0.0061 (6)	0.0060 (7)
C10	0.0483 (8)	0.0646 (10)	0.0544 (9)	0.0013 (7)	−0.0038 (6)	0.0095 (7)
C11	0.0496 (7)	0.0517 (8)	0.0462 (7)	0.0034 (6)	−0.0015 (6)	0.0019 (6)
C12	0.0445 (7)	0.0425 (7)	0.0450 (7)	0.0025 (6)	0.0014 (5)	−0.0011 (6)
C13	0.0502 (7)	0.0496 (8)	0.0444 (7)	−0.0016 (6)	0.0041 (6)	0.0045 (6)
C14	0.0442 (7)	0.0533 (9)	0.0530 (8)	−0.0057 (6)	0.0052 (6)	0.0002 (7)
C15	0.0456 (7)	0.0467 (8)	0.0490 (7)	−0.0011 (6)	−0.0042 (6)	−0.0034 (6)
C16	0.0529 (8)	0.0536 (8)	0.0414 (7)	−0.0046 (6)	0.0013 (6)	0.0026 (6)
C17	0.0444 (7)	0.0559 (9)	0.0468 (7)	−0.0025 (6)	0.0061 (6)	−0.0008 (6)
O1	0.0499 (6)	0.0655 (7)	0.0491 (6)	0.0006 (5)	−0.0073 (4)	0.0076 (5)
O2	0.0602 (7)	0.1083 (11)	0.0573 (7)	−0.0042 (7)	−0.0050 (5)	0.0175 (7)
Cl1	0.0526 (2)	0.0844 (3)	0.0690 (3)	−0.00645 (19)	−0.01679 (19)	0.0098 (2)

C1—C8	1.335 (2)	C9—C10	1.468 (2)
C1—C2	1.423 (2)	C10—C11	1.323 (2)
C1—H1	0.93	C10—H10	0.93
C2—C7	1.389 (2)	C11—C12	1.4641 (19)
C2—C3	1.405 (2)	C11—H11	0.93
C3—C4	1.368 (3)	C12—C13	1.3954 (19)
C3—H3	0.93	C12—C17	1.398 (2)
C4—C5	1.388 (3)	C13—C14	1.382 (2)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.365 (3)	C14—C15	1.377 (2)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.386 (2)	C15—C16	1.384 (2)
C6—H6	0.93	C15—Cl1	1.7352 (15)
C7—O1	1.3690 (18)	C16—C17	1.378 (2)
C8—O1	1.3820 (17)	C16—H16	0.93
C8—C9	1.469 (2)	C17—H17	0.93
C9—O2	1.2216 (19)
C8—C1—C2	107.24 (13)	C10—C9—C8	115.33 (14)
C8—C1—H1	126.4	C11—C10—C9	122.03 (15)
C2—C1—H1	126.4	C11—C10—H10	119.0
C7—C2—C3	118.89 (14)	C9—C10—H10	119.0
C7—C2—C1	105.49 (14)	C10—C11—C12	126.58 (15)
C3—C2—C1	135.61 (15)	C10—C11—H11	116.7
C4—C3—C2	118.14 (16)	C12—C11—H11	116.7
C4—C3—H3	120.9	C13—C12—C17	118.30 (13)
C2—C3—H3	120.9	C13—C12—C11	119.20 (13)
C3—C4—C5	121.44 (17)	C17—C12—C11	122.45 (13)
C3—C4—H4	119.3	C14—C13—C12	121.23 (13)
C5—C4—H4	119.3	C14—C13—H13	119.4
C6—C5—C4	121.88 (17)	C12—C13—H13	119.4
C6—C5—H5	119.1	C15—C14—C13	118.93 (13)
C4—C5—H5	119.1	C15—C14—H14	120.5
C5—C6—C7	116.70 (16)	C13—C14—H14	120.5
C5—C6—H6	121.7	C14—C15—C16	121.37 (13)
C7—C6—H6	121.7	C14—C15—Cl1	119.95 (12)
O1—C7—C6	126.81 (14)	C16—C15—Cl1	118.68 (11)
O1—C7—C2	110.25 (12)	C17—C16—C15	119.29 (13)
C6—C7—C2	122.94 (15)	C17—C16—H16	120.4
C1—C8—O1	111.44 (14)	C15—C16—H16	120.4
C1—C8—C9	131.92 (14)	C16—C17—C12	120.83 (13)
O1—C8—C9	116.62 (14)	C16—C17—H17	119.6
O2—C9—C10	122.98 (15)	C12—C17—H17	119.6
O2—C9—C8	121.69 (14)	C7—O1—C8	105.57 (12)
C8—C1—C2—C7	0.86 (17)	O2—C9—C10—C11	−14.3 (3)
C8—C1—C2—C3	−178.91 (18)	C8—C9—C10—C11	165.10 (16)
C7—C2—C3—C4	0.8 (2)	C9—C10—C11—C12	179.27 (15)
C1—C2—C3—C4	−179.41 (18)	C10—C11—C12—C13	−176.76 (16)
C2—C3—C4—C5	0.4 (3)	C10—C11—C12—C17	0.4 (3)
C3—C4—C5—C6	−1.0 (3)	C17—C12—C13—C14	−2.4 (2)
C4—C5—C6—C7	0.4 (3)	C11—C12—C13—C14	174.96 (14)
C5—C6—C7—O1	−179.32 (16)	C12—C13—C14—C15	0.9 (2)
C5—C6—C7—C2	0.9 (3)	C13—C14—C15—C16	0.9 (2)
C3—C2—C7—O1	178.67 (14)	C13—C14—C15—Cl1	−178.88 (12)
C1—C2—C7—O1	−1.15 (17)	C14—C15—C16—C17	−1.2 (2)
C3—C2—C7—C6	−1.5 (2)	Cl1—C15—C16—C17	178.57 (12)
C1—C2—C7—C6	178.64 (15)	C15—C16—C17—C12	−0.3 (2)
C2—C1—C8—O1	−0.28 (18)	C13—C12—C17—C16	2.0 (2)
C2—C1—C8—C9	−179.04 (16)	C11—C12—C17—C16	−175.20 (14)
C1—C8—C9—O2	−172.20 (18)	C6—C7—O1—C8	−178.80 (16)
O1—C8—C9—O2	9.1 (2)	C2—C7—O1—C8	0.98 (16)
C1—C8—C9—C10	8.3 (3)	C1—C8—O1—C7	−0.42 (17)
O1—C8—C9—C10	−170.36 (14)	C9—C8—O1—C7	178.55 (13)