1-(4-Chloro­phen­yl)-3-(5-methyl-2-fur­yl)prop-2-en-1-one

Guo, H.-M.

doi:10.1107/S1600536809044456

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2921

https://doi.org/10.1107/S1600536809044456

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1-(4-Chlorophenyl)-3-(5-methyl-2-furyl)prop-2-en-1-one

Huan-Mei Guo ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: huanmeiguo@163.com

(Received 8 October 2009; accepted 26 October 2009; online 31 October 2009)

The title compound, C₁₄H₁₁ClO₂, was prepared from 4-chlorohypnone and 5-methylfurfural 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 interactions.

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_r = 246.68
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.180
S = 1.07
2988 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) -x, -y, -z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044456/tk2555Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds with multiple biological actions, including anti-inflammatory (Hsieh et al., 1998) and anti-oxidant (Anto et al., 1994) activities. Of particular interest is the effectiveness of chalcones against cancer (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds, we synthesized the title chalcone, (I), and report its crystal structure herein.

The molecular structure of (I), Fig. 1, comprises a furan ring and a chlorophenyl group. These groups are not co-planar as seen in the value of the dihedral angle between them of 7.71 (2)°. Bond distances and angles conform to literature precedents (Guo, et al., 2008). There are intre- and inter-molecular C—H···O interactions that stabilize the molecular and crystal structures, respectively (Table 1). The intermolecular contacts lead to the formation of centrosymmetric dimers.

Related literature top

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 top

Compound (I) was prepared in 80% yield by stirring an ethanol (30 ml) mixture comprising 4-chlorohypnone (0.02 mol), 5-methylfurfural (0.02 mol) and 10% NaOH (10 ml) for 3 h. Single crystals were obtailed by recrystallization of (I) from ethyl acetate at room temperature.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

1-(4-Chlorophenyl)-3-(5-methyl-2-furyl)prop-2-en-1-one top

Crystal data top

C₁₄H₁₁ClO₂	F(000) = 512
M_r = 246.68	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0853P)² + 0.305P] where P = (F_o² + 2F_c²)/3
2988 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₁ClO₂	V = 1214.4 (6) Å³
M_r = 246.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.350 (3) Å	µ = 0.30 mm⁻¹
b = 15.732 (5) Å	T = 273 K
c = 9.660 (3) Å	0.50 × 0.30 × 0.25 mm
β = 106.882 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2055 reflections with I > 2σ(I)
7894 measured reflections	R_int = 0.018
2988 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.07	Δρ_max = 0.32 e Å⁻³
2988 reflections	Δρ_min = −0.36 e Å⁻³
154 parameters

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClO₂
M_r	246.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	8.350 (3), 15.732 (5), 9.660 (3)
β (°)	106.882 (5)
V (Å³)	1214.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.50 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7894, 2988, 2055
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.180, 1.07
No. of reflections	2988
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.36

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z.

Acknowledgements

The author would like to thank the National Natural Science Foundation of Shandong (Y2008B29) and Weifang University for research support.

References

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