3-(5-Methyl-2-fur­yl)-1-(p-tol­yl)-2-propen-1-one

Guo, H.-M.; Wang, X.-B.; Jian, F.-F.

doi:10.1107/S1600536808029152

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1951

doi:10.1107/S1600536808029152

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3-(5-Methyl-2-furyl)-1-(p-tolyl)-2-propen-1-one

Huan-Mei Guo,^a Xian-Bing Wang ^b and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bDepartment of Equipment, Weifang University, Weifang 261061, People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 15 August 2008; accepted 11 September 2008; online 17 September 2008)

The title compound, C₁₅H₁₄O₂, was prepared from 4-methylhypnone and 5-methylfurfural by Clasion–Schmidt condensation. All of the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the benzene ring and furan ring is 5.31 (2).

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 ); Anto et al. (1994 ). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 ); Dimmock et al. (1998 ). For bond-length and angle data, see: Ali et al. (2005 ); Zhou (2007 ).

Experimental

Crystal data

C₁₅H₁₄O₂
M_r = 226.26
Monoclinic, P 2₁ /c
a = 8.0394 (8) Å
b = 17.0278 (17) Å
c = 10.6550 (8) Å
β = 121.347 (6)°
V = 1245.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
7980 measured reflections
2985 independent reflections
1706 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.136
S = 1.02
2985 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.11 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.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808029152/at2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029152/at2615Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al., 1994). Of particular interest, the effectiveness of chalcones against cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds we synthesized the title compound (I), and describe its structure here.

In the structure of (I) (Fig. 1), all of the bond lengths and bond angles fall in the normal range (Zhou, 2007; Ali et al., 2005). The dihedral angles formed by the benzene ring and furan ring is 5.31 (2)°. There are some weak C—H···O hydrogen bonds in the crystal structure (Table 1).

Related literature top

For the biological activity of chalcones, see: Hsieh et al. (1998);

Anto et al. (1994). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000); Dimmock et al. (1998).

For bond-length and angle data, see: Ali et al. (2005); Zhou (2007).

Experimental top

A mixture of the 5-methylfurfural (0.02 mol), and 4-methylhypnone (0.02 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 mL) for 3 h to afford the title compound (yield 85%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

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 structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

3-(5-Methyl-2-furyl)-1-(p-tolyl)-2-propen-1-one top

Crystal data top

C₁₅H₁₄O₂	F(000) = 480
M_r = 226.26	D_x = 1.206 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1770 reflections
a = 8.0394 (8) Å	θ = 0.4–27.5°
b = 17.0278 (17) Å	µ = 0.08 mm⁻¹
c = 10.6550 (8) Å	T = 293 K
β = 121.347 (6)°	Bar, colourless
V = 1245.7 (2) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.2°, θ_min = 2.4°
phi and ω scans	h = −8→10
7980 measured reflections	k = −17→22
2985 independent reflections	l = −13→13

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0613P)² + 0.0738P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2985 reflections	Δρ_max = 0.17 e Å⁻³
155 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Crystal data top

C₁₅H₁₄O₂	V = 1245.7 (2) Å³
M_r = 226.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0394 (8) Å	µ = 0.08 mm⁻¹
b = 17.0278 (17) Å	T = 293 K
c = 10.6550 (8) Å	0.2 × 0.2 × 0.2 mm
β = 121.347 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1706 reflections with I > 2σ(I)
7980 measured reflections	R_int = 0.026
2985 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
2985 reflections	Δρ_min = −0.11 e Å⁻³
155 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
O1	−0.32694 (14)	−0.22464 (6)	−0.56944 (10)	0.0574 (3)
O2	0.14482 (19)	−0.01503 (7)	−0.24561 (13)	0.0810 (4)
C1	−0.5507 (3)	−0.33021 (11)	−0.7020 (2)	0.0892 (6)
H1A	−0.6226	−0.3521	−0.7991	0.134*
H1B	−0.6395	−0.3140	−0.6722	0.134*
H1C	−0.4632	−0.3691	−0.6347	0.134*
C2	−0.4379 (2)	−0.26168 (9)	−0.70182 (17)	0.0582 (4)
C3	−0.4181 (2)	−0.22529 (10)	−0.80412 (18)	0.0656 (4)
H3A	−0.4779	−0.2393	−0.9026	0.079*
C4	−0.2899 (3)	−0.16169 (10)	−0.73553 (18)	0.0665 (4)
H4A	−0.2497	−0.1259	−0.7804	0.080*
C5	−0.2364 (2)	−0.16241 (8)	−0.59293 (16)	0.0545 (4)
C6	−0.1121 (2)	−0.11417 (9)	−0.47132 (18)	0.0590 (4)
H6A	−0.0541	−0.0723	−0.4903	0.071*
C7	−0.0686 (2)	−0.12165 (9)	−0.33318 (17)	0.0577 (4)
H7A	−0.1275	−0.1613	−0.3099	0.069*
C8	0.0699 (2)	−0.06898 (9)	−0.21687 (17)	0.0591 (4)
C9	0.1224 (2)	−0.08231 (9)	−0.06208 (16)	0.0558 (4)
C10	0.0379 (2)	−0.13889 (10)	−0.02027 (18)	0.0683 (5)
H10A	−0.0550	−0.1724	−0.0908	0.082*
C11	0.0888 (3)	−0.14648 (11)	0.1236 (2)	0.0761 (5)
H11A	0.0287	−0.1850	0.1483	0.091*
C12	0.2260 (3)	−0.09881 (10)	0.23223 (19)	0.0701 (5)
C13	0.3126 (3)	−0.04334 (11)	0.1911 (2)	0.0802 (5)
H13A	0.4077	−0.0108	0.2624	0.096*
C14	0.2624 (3)	−0.03474 (10)	0.04727 (19)	0.0734 (5)
H14A	0.3235	0.0036	0.0231	0.088*
C15	0.2803 (3)	−0.10657 (13)	0.3896 (2)	0.0940 (6)
H15A	0.2064	−0.1483	0.3979	0.141*
H15B	0.2525	−0.0582	0.4215	0.141*
H15C	0.4168	−0.1181	0.4500	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0672 (6)	0.0599 (6)	0.0517 (6)	−0.0065 (5)	0.0355 (5)	−0.0031 (5)
O2	0.1026 (9)	0.0684 (7)	0.0750 (8)	−0.0265 (7)	0.0484 (7)	−0.0067 (6)
C1	0.1063 (15)	0.0854 (13)	0.0788 (13)	−0.0308 (11)	0.0503 (11)	−0.0160 (10)
C2	0.0607 (9)	0.0627 (9)	0.0534 (9)	−0.0021 (7)	0.0313 (7)	−0.0068 (7)
C3	0.0744 (10)	0.0738 (10)	0.0502 (9)	0.0001 (9)	0.0335 (8)	−0.0025 (8)
C4	0.0812 (11)	0.0691 (10)	0.0588 (10)	−0.0043 (9)	0.0430 (9)	0.0049 (8)
C5	0.0587 (9)	0.0546 (9)	0.0566 (9)	0.0013 (7)	0.0345 (7)	0.0025 (7)
C6	0.0630 (9)	0.0544 (9)	0.0658 (10)	−0.0025 (7)	0.0379 (8)	−0.0015 (7)
C7	0.0614 (9)	0.0544 (9)	0.0602 (10)	−0.0044 (7)	0.0337 (8)	−0.0019 (7)
C8	0.0624 (9)	0.0513 (9)	0.0649 (10)	−0.0011 (7)	0.0341 (8)	−0.0021 (7)
C9	0.0567 (9)	0.0517 (8)	0.0568 (9)	0.0029 (7)	0.0280 (7)	−0.0030 (7)
C10	0.0672 (10)	0.0725 (11)	0.0608 (11)	−0.0082 (8)	0.0302 (8)	−0.0020 (8)
C11	0.0758 (12)	0.0849 (12)	0.0676 (12)	−0.0017 (10)	0.0374 (10)	0.0088 (9)
C12	0.0721 (11)	0.0747 (11)	0.0597 (11)	0.0223 (9)	0.0315 (9)	0.0060 (8)
C13	0.0872 (13)	0.0762 (12)	0.0610 (11)	−0.0049 (10)	0.0273 (10)	−0.0138 (9)
C14	0.0856 (12)	0.0631 (10)	0.0683 (12)	−0.0131 (9)	0.0378 (10)	−0.0096 (8)
C15	0.1016 (14)	0.1128 (16)	0.0632 (12)	0.0270 (12)	0.0398 (11)	0.0108 (10)

Geometric parameters (Å, º) top

O1—C2	1.3689 (17)	C7—H7A	0.9300
O1—C5	1.3800 (16)	C8—C9	1.492 (2)
O2—C8	1.2218 (17)	C9—C10	1.379 (2)
C1—C2	1.477 (2)	C9—C14	1.384 (2)
C1—H1A	0.9600	C10—C11	1.372 (2)
C1—H1B	0.9600	C10—H10A	0.9300
C1—H1C	0.9600	C11—C12	1.374 (2)
C2—C3	1.333 (2)	C11—H11A	0.9300
C3—C4	1.409 (2)	C12—C13	1.374 (2)
C3—H3A	0.9300	C12—C15	1.503 (2)
C4—C5	1.347 (2)	C13—C14	1.374 (2)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.416 (2)	C14—H14A	0.9300
C6—C7	1.330 (2)	C15—H15A	0.9600
C6—H6A	0.9300	C15—H15B	0.9600
C7—C8	1.464 (2)	C15—H15C	0.9600

C2—O1—C5	106.82 (11)	O2—C8—C9	119.91 (14)
C2—C1—H1A	109.5	C7—C8—C9	119.74 (14)
C2—C1—H1B	109.5	C10—C9—C14	117.28 (15)
H1A—C1—H1B	109.5	C10—C9—C8	124.02 (14)
C2—C1—H1C	109.5	C14—C9—C8	118.69 (15)
H1A—C1—H1C	109.5	C11—C10—C9	121.08 (16)
H1B—C1—H1C	109.5	C11—C10—H10A	119.5
C3—C2—O1	109.70 (14)	C9—C10—H10A	119.5
C3—C2—C1	134.46 (16)	C10—C11—C12	121.87 (17)
O1—C2—C1	115.83 (13)	C10—C11—H11A	119.1
C2—C3—C4	107.42 (15)	C12—C11—H11A	119.1
C2—C3—H3A	126.3	C11—C12—C13	117.08 (17)
C4—C3—H3A	126.3	C11—C12—C15	121.90 (18)
C5—C4—C3	107.23 (14)	C13—C12—C15	121.02 (18)
C5—C4—H4A	126.4	C12—C13—C14	121.72 (17)
C3—C4—H4A	126.4	C12—C13—H13A	119.1
C4—C5—O1	108.82 (13)	C14—C13—H13A	119.1
C4—C5—C6	133.33 (14)	C13—C14—C9	120.96 (17)
O1—C5—C6	117.85 (13)	C13—C14—H14A	119.5
C7—C6—C5	127.68 (15)	C9—C14—H14A	119.5
C7—C6—H6A	116.2	C12—C15—H15A	109.5
C5—C6—H6A	116.2	C12—C15—H15B	109.5
C6—C7—C8	121.64 (14)	H15A—C15—H15B	109.5
C6—C7—H7A	119.2	C12—C15—H15C	109.5
C8—C7—H7A	119.2	H15A—C15—H15C	109.5
O2—C8—C7	120.35 (15)	H15B—C15—H15C	109.5

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₂
M_r	226.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0394 (8), 17.0278 (17), 10.6550 (8)
β (°)	121.347 (6)
V (Å³)	1245.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7980, 2985, 1706
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.136, 1.02
No. of reflections	2985
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.11

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

Acknowledgements

The authors thank the Natural Science Foundation of Wei Fang University (grant No. 2008Z04).

References

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