1-(4-Chloro-phen-yl)-3-(5-methyl-2-fur-yl)prop-2-en-1-one.

The title compound, C(14)H(11)ClO(2), was prepared from 4-chloro-hypnone and 5-methyl-furfural by an aldol condensation reaction. The dihedral angle formed between the two benzene rings is 7.71 (2)°. The crystal structure is stabilized by C-H⋯O inter-actions.

Related literature

For the biological activity of chalcones, see: Anto et al. (1994 ▶); Dimmock et al. (1998 ▶); Hsieh et al. (1998 ▶); De Vincenzo et al. (2000 ▶). For a related structure, see: Guo et al. (2008 ▶).

Experimental

Crystal data

C14H11ClO2

M = 246.68

Monoclinic,

a = 8.350 (3) Å

b = 15.732 (5) Å

c = 9.660 (3) Å

β = 106.882 (5)°

V = 1214.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 273 K

0.50 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

7894 measured reflections

2988 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.180

S = 1.07

2988 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.36 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044456/tk2555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044456/tk2555Isup2.hkl

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

C14H11ClO2	F(000) = 512
Mr = 246.68	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2055 reflections
a = 8.350 (3) Å	θ = 2.6–28.4°
b = 15.732 (5) Å	µ = 0.30 mm−1
c = 9.660 (3) Å	T = 273 K
β = 106.882 (5)°	Block, yellow
V = 1214.4 (6) Å3	0.50 × 0.30 × 0.25 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
graphite	θmax = 28.4°, θmin = 2.6°
φ and ω scans	h = −10→11
7894 measured reflections	k = −20→21
2988 independent reflections	l = −11→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0853P)2 + 0.305P] where P = (Fo2 + 2Fc2)/3
2988 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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
Cl	0.67915 (10)	0.11664 (5)	0.96441 (7)	0.0964 (3)
O2	0.29242 (17)	0.21735 (9)	0.00449 (14)	0.0596 (4)
C14	0.1656 (3)	0.10736 (14)	0.1064 (3)	0.0658 (5)
H14A	0.0836	0.0655	0.0908	0.079*
C13	0.2634 (3)	0.11657 (13)	0.2411 (2)	0.0626 (5)
H13A	0.3490	0.1566	0.2598	0.075*
C10	0.1736 (3)	0.15490 (15)	−0.0158 (2)	0.0629 (5)
C12	0.2409 (3)	0.06591 (13)	0.3607 (3)	0.0650 (5)
C5	0.4834 (3)	0.13765 (16)	0.5410 (2)	0.0710 (6)
H5A	0.5052	0.1688	0.4666	0.085*
C6	0.3508 (3)	0.08210 (12)	0.5095 (2)	0.0587 (5)
C4	0.5843 (3)	0.14810 (17)	0.6800 (3)	0.0774 (7)
H4A	0.6746	0.1854	0.6994	0.093*
O1	0.1329 (2)	0.01152 (11)	0.3404 (2)	0.0909 (6)
C3	0.5513 (3)	0.10340 (14)	0.7892 (2)	0.0670 (6)
C11	0.2738 (3)	0.25576 (15)	−0.1251 (2)	0.0653 (6)
C2	0.4203 (4)	0.04941 (17)	0.7630 (3)	0.0860 (8)
H2A	0.3984	0.0195	0.8386	0.103*
C9	0.0819 (3)	0.15581 (19)	−0.1574 (3)	0.0800 (7)
H9A	−0.0076	0.1203	−0.2009	0.096*
C8	0.1463 (3)	0.21949 (18)	−0.2252 (3)	0.0783 (7)
H8A	0.1079	0.2343	−0.3224	0.094*
C1	0.3202 (4)	0.03911 (16)	0.6244 (3)	0.0844 (8)
H1A	0.2293	0.0023	0.6067	0.101*
C7	0.3947 (3)	0.32399 (17)	−0.1277 (3)	0.0853 (7)
H7A	0.4700	0.3315	−0.0324	0.128*
H7B	0.3355	0.3761	−0.1594	0.128*
H7C	0.4572	0.3086	−0.1932	0.128*

	U11	U22	U33	U12	U13	U23
Cl	0.1060 (6)	0.1184 (6)	0.0598 (4)	0.0105 (4)	0.0160 (4)	0.0124 (3)
O2	0.0562 (8)	0.0653 (8)	0.0492 (7)	0.0017 (6)	0.0026 (6)	−0.0025 (6)
C14	0.0611 (12)	0.0613 (12)	0.0731 (14)	−0.0025 (10)	0.0163 (10)	−0.0093 (10)
C13	0.0600 (12)	0.0571 (11)	0.0675 (13)	−0.0025 (9)	0.0137 (10)	−0.0028 (9)
C10	0.0532 (11)	0.0707 (13)	0.0586 (12)	0.0006 (9)	0.0068 (9)	−0.0124 (9)
C12	0.0682 (13)	0.0501 (11)	0.0779 (14)	−0.0017 (10)	0.0231 (11)	−0.0008 (10)
C5	0.0748 (14)	0.0776 (14)	0.0610 (12)	−0.0125 (12)	0.0201 (11)	0.0129 (11)
C6	0.0644 (12)	0.0462 (10)	0.0682 (12)	0.0024 (9)	0.0232 (10)	0.0047 (9)
C4	0.0774 (15)	0.0846 (16)	0.0666 (14)	−0.0147 (13)	0.0151 (11)	0.0133 (12)
O1	0.0971 (13)	0.0774 (11)	0.0948 (13)	−0.0329 (10)	0.0224 (10)	−0.0050 (9)
C3	0.0738 (14)	0.0675 (13)	0.0610 (12)	0.0142 (11)	0.0213 (10)	0.0084 (10)
C11	0.0633 (12)	0.0738 (13)	0.0535 (11)	0.0127 (10)	0.0088 (9)	−0.0016 (9)
C2	0.104 (2)	0.0835 (17)	0.0741 (16)	−0.0067 (15)	0.0314 (15)	0.0243 (13)
C9	0.0655 (13)	0.1002 (18)	0.0643 (13)	−0.0104 (13)	0.0028 (11)	−0.0208 (13)
C8	0.0738 (14)	0.1012 (18)	0.0504 (11)	0.0100 (13)	0.0030 (10)	−0.0061 (11)
C1	0.0927 (17)	0.0735 (15)	0.0897 (19)	−0.0194 (13)	0.0306 (15)	0.0162 (13)
C7	0.0932 (18)	0.0817 (16)	0.0752 (15)	0.0017 (14)	0.0154 (14)	0.0149 (13)

Cl—C3	1.731 (2)	C4—C3	1.361 (3)
O2—C11	1.358 (3)	C4—H4A	0.9300
O2—C10	1.370 (3)	C3—C2	1.349 (4)
C14—C13	1.328 (3)	C11—C8	1.340 (3)
C14—C10	1.415 (3)	C11—C7	1.479 (4)
C14—H14A	0.9300	C2—C1	1.367 (4)
C13—C12	1.460 (3)	C2—H2A	0.9300
C13—H13A	0.9300	C9—C8	1.388 (4)
C10—C9	1.360 (3)	C9—H9A	0.9300
C12—O1	1.217 (3)	C8—H8A	0.9300
C12—C6	1.485 (3)	C1—H1A	0.9300
C5—C4	1.372 (3)	C7—H7A	0.9600
C5—C6	1.373 (3)	C7—H7B	0.9600
C5—H5A	0.9300	C7—H7C	0.9600
C6—C1	1.385 (3)
C11—O2—C10	107.65 (16)	C2—C3—Cl	119.68 (19)
C13—C14—C10	126.5 (2)	C4—C3—Cl	119.3 (2)
C13—C14—H14A	116.7	C8—C11—O2	109.3 (2)
C10—C14—H14A	116.7	C8—C11—C7	134.4 (2)
C14—C13—C12	122.1 (2)	O2—C11—C7	116.28 (19)
C14—C13—H13A	118.9	C3—C2—C1	119.4 (2)
C12—C13—H13A	118.9	C3—C2—H2A	120.3
C9—C10—O2	108.0 (2)	C1—C2—H2A	120.3
C9—C10—C14	134.1 (2)	C10—C9—C8	107.5 (2)
O2—C10—C14	117.89 (17)	C10—C9—H9A	126.3
O1—C12—C13	121.0 (2)	C8—C9—H9A	126.3
O1—C12—C6	119.8 (2)	C11—C8—C9	107.6 (2)
C13—C12—C6	119.15 (18)	C11—C8—H8A	126.2
C4—C5—C6	121.3 (2)	C9—C8—H8A	126.2
C4—C5—H5A	119.4	C2—C1—C6	121.6 (2)
C6—C5—H5A	119.4	C2—C1—H1A	119.2
C5—C6—C1	117.3 (2)	C6—C1—H1A	119.2
C5—C6—C12	123.70 (19)	C11—C7—H7A	109.5
C1—C6—C12	119.0 (2)	C11—C7—H7B	109.5
C3—C4—C5	119.4 (2)	H7A—C7—H7B	109.5
C3—C4—H4A	120.3	C11—C7—H7C	109.5
C5—C4—H4A	120.3	H7A—C7—H7C	109.5
C2—C3—C4	121.0 (2)	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.93	2.53	3.380 (4)	153
C14—H14A···O1	0.93	2.47	2.795 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.93	2.53	3.380 (4)	153
C14—H14A⋯O1	0.93	2.47	2.795 (2)	100

Symmetry code: (i) .