3-(5-Methyl-2-fur-yl)-1-(p-tol-yl)-2-propen-1-one.

The title compound, C(15)H(14)O(2), was prepared from 4-methyl-hypnone and 5-methyl-furfural 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 = 226.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.136

S = 1.02

2985 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −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.

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

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

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

C15H14O2	F(000) = 480
Mr = 226.26	Dx = 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

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

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(Fo2) + (0.0613P)2 + 0.0738P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2985 reflections	Δρmax = 0.17 e Å−3
155 parameters	Δρmin = −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)

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
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*

	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)

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