(1E,4E)-1,5-Bis(2,4-dimethyl-phen-yl)penta-1,4-dien-3-one.

In the title compound, C(21)H(22)O, a derivative of the biologically active compound curcumin, the dihedral angle between the aromatic ring planes is 20.57 (11)°.

Related literature

For backgound to cucucmin and its biological properties, see: Began et al. (1999 ▶); Gautam et al. (2007 ▶); Liang et al. (2008 ▶); Liang, Shao et al. (2009 ▶); Liang, Tian et al. (2007 ▶); Liang, Yang et al. (2007 ▶); Liang, Zhou et al. (2009 ▶); Maheshwari et al. (2006 ▶); Zhao et al. (2009 ▶).

Experimental

Crystal data

C21H22O

M = 290.39

Monoclinic,

a = 4.9548 (7) Å

b = 26.555 (4) Å

c = 12.9632 (19) Å

β = 94.090 (3)°

V = 1701.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.42 × 0.37 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.769, T max = 1.000

8842 measured reflections

3128 independent reflections

2007 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.173

S = 0.97

3128 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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, global. DOI: 10.1107/S1600536809033583/hb5050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033583/hb5050Isup2.hkl

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

C21H22O	F(000) = 624
Mr = 290.39	Dx = 1.134 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1845 reflections
a = 4.9548 (7) Å	θ = 4.4–44.1°
b = 26.555 (4) Å	µ = 0.07 mm−1
c = 12.9632 (19) Å	T = 293 K
β = 94.090 (3)°	Prism, green
V = 1701.3 (4) Å3	0.42 × 0.37 × 0.26 mm
Z = 4

Bruker SMART CCD diffractometer	3128 independent reflections
Radiation source: fine-focus sealed tube	2007 reflections with I > 2σ(I)
graphite	Rint = 0.095
ω scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→6
Tmin = 0.769, Tmax = 1.000	k = −31→32
8842 measured reflections	l = −7→15

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0858P)2] where P = (Fo2 + 2Fc2)/3
3128 reflections	(Δ/σ)max = 0.057
203 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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
O1	1.4353 (4)	0.35616 (7)	0.08357 (12)	0.0700 (5)
C1	1.2047 (5)	0.36963 (8)	0.09662 (16)	0.0510 (6)
C2	1.0758 (5)	0.35782 (8)	0.19171 (16)	0.0528 (6)
H2	0.9031	0.3703	0.1994	0.063*
C3	1.1920 (4)	0.33037 (8)	0.26714 (16)	0.0479 (6)
H3	1.3621	0.3173	0.2566	0.057*
C4	1.0435 (5)	0.39838 (8)	0.01739 (16)	0.0545 (6)
H4	0.8698	0.4083	0.0313	0.065*
C5	1.1329 (5)	0.41070 (8)	−0.07216 (16)	0.0516 (6)
H5	1.3019	0.3982	−0.0860	0.062*
C6	0.9942 (4)	0.44212 (7)	−0.15263 (16)	0.0473 (6)
C7	1.0565 (4)	0.43873 (7)	−0.25633 (16)	0.0493 (6)
C8	0.9237 (5)	0.47084 (8)	−0.32771 (17)	0.0557 (6)
H8	0.9633	0.4684	−0.3966	0.067*
C9	0.7367 (5)	0.50614 (8)	−0.30192 (18)	0.0570 (6)
C10	0.6759 (5)	0.50852 (9)	−0.19985 (19)	0.0645 (7)
H10	0.5482	0.5316	−0.1801	0.077*
C11	0.8023 (5)	0.47709 (9)	−0.12683 (18)	0.0603 (6)
H11	0.7577	0.4794	−0.0585	0.072*
C12	1.0812 (4)	0.31833 (7)	0.36552 (15)	0.0455 (5)
C13	0.8956 (5)	0.34978 (8)	0.40688 (17)	0.0564 (6)
H13	0.8429	0.3789	0.3710	0.068*
C14	0.7855 (5)	0.33986 (9)	0.49876 (18)	0.0614 (7)
H14	0.6607	0.3620	0.5239	0.074*
C15	0.8597 (5)	0.29692 (9)	0.55428 (16)	0.0544 (6)
C16	1.0474 (4)	0.26532 (9)	0.51378 (16)	0.0535 (6)
H16	1.0998	0.2365	0.5506	0.064*
C17	1.1613 (4)	0.27453 (8)	0.42090 (15)	0.0466 (5)
C18	1.2581 (5)	0.40116 (8)	−0.29188 (17)	0.0626 (7)
H18A	1.2595	0.4025	−0.3658	0.094*
H18B	1.2081	0.3679	−0.2712	0.094*
H18C	1.4350	0.4091	−0.2613	0.094*
C19	0.5986 (6)	0.54084 (9)	−0.3819 (2)	0.0795 (8)
H19A	0.6863	0.5383	−0.4453	0.119*
H19B	0.6098	0.5749	−0.3572	0.119*
H19C	0.4120	0.5313	−0.3938	0.119*
C20	1.3587 (5)	0.23772 (9)	0.38199 (18)	0.0640 (7)
H20A	1.3890	0.2110	0.4313	0.096*
H20B	1.5267	0.2545	0.3725	0.096*
H20C	1.2871	0.2240	0.3172	0.096*
C21	0.7377 (5)	0.28438 (12)	0.65406 (18)	0.0784 (8)
H21A	0.6361	0.3127	0.6761	0.118*
H21B	0.8792	0.2765	0.7060	0.118*
H21C	0.6198	0.2559	0.6438	0.118*

	U11	U22	U33	U12	U13	U23
O1	0.0565 (11)	0.0924 (13)	0.0619 (11)	0.0062 (9)	0.0100 (9)	0.0172 (9)
C1	0.0505 (14)	0.0541 (13)	0.0482 (13)	−0.0077 (11)	0.0023 (11)	0.0032 (10)
C2	0.0491 (13)	0.0618 (14)	0.0476 (13)	−0.0010 (11)	0.0044 (11)	0.0058 (11)
C3	0.0476 (13)	0.0479 (12)	0.0482 (13)	−0.0034 (10)	0.0043 (10)	−0.0009 (10)
C4	0.0522 (14)	0.0625 (14)	0.0492 (13)	0.0007 (11)	0.0061 (11)	0.0072 (11)
C5	0.0558 (14)	0.0491 (13)	0.0498 (13)	−0.0050 (10)	0.0036 (11)	−0.0002 (10)
C6	0.0546 (14)	0.0411 (11)	0.0459 (13)	−0.0053 (10)	0.0016 (10)	−0.0001 (9)
C7	0.0548 (13)	0.0456 (12)	0.0474 (13)	−0.0087 (10)	0.0037 (11)	0.0022 (10)
C8	0.0668 (16)	0.0528 (13)	0.0474 (13)	−0.0088 (12)	0.0034 (11)	0.0045 (11)
C9	0.0682 (16)	0.0427 (12)	0.0588 (15)	−0.0048 (12)	−0.0049 (12)	0.0009 (11)
C10	0.0678 (17)	0.0532 (14)	0.0716 (17)	0.0092 (12)	−0.0008 (13)	−0.0069 (13)
C11	0.0715 (17)	0.0579 (14)	0.0520 (14)	−0.0001 (12)	0.0084 (12)	−0.0018 (11)
C12	0.0447 (12)	0.0481 (12)	0.0435 (12)	−0.0012 (10)	0.0020 (10)	−0.0009 (10)
C13	0.0607 (15)	0.0549 (13)	0.0539 (14)	0.0141 (11)	0.0074 (12)	0.0058 (11)
C14	0.0598 (15)	0.0696 (16)	0.0564 (15)	0.0172 (13)	0.0156 (12)	0.0002 (12)
C15	0.0517 (14)	0.0657 (15)	0.0461 (13)	0.0025 (12)	0.0056 (11)	0.0027 (11)
C16	0.0531 (14)	0.0586 (14)	0.0487 (13)	0.0035 (11)	0.0031 (11)	0.0115 (11)
C17	0.0455 (12)	0.0462 (12)	0.0479 (13)	0.0023 (10)	0.0015 (10)	0.0012 (10)
C18	0.0700 (16)	0.0639 (15)	0.0549 (14)	0.0062 (13)	0.0110 (12)	−0.0017 (12)
C19	0.095 (2)	0.0616 (16)	0.0795 (19)	0.0047 (14)	−0.0140 (16)	0.0103 (14)
C20	0.0720 (17)	0.0580 (14)	0.0632 (15)	0.0108 (13)	0.0140 (13)	0.0003 (12)
C21	0.0716 (18)	0.107 (2)	0.0586 (16)	0.0085 (16)	0.0199 (13)	0.0149 (15)

O1—C1	1.221 (3)	C12—C17	1.409 (3)
C1—C2	1.462 (3)	C13—C14	1.370 (3)
C1—C4	1.469 (3)	C13—H13	0.9300
C2—C3	1.319 (3)	C14—C15	1.384 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C12	1.459 (3)	C15—C16	1.383 (3)
C3—H3	0.9300	C15—C21	1.504 (3)
C4—C5	1.313 (3)	C16—C17	1.388 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.468 (3)	C17—C20	1.496 (3)
C5—H5	0.9300	C18—H18A	0.9600
C6—C11	1.387 (3)	C18—H18B	0.9600
C6—C7	1.403 (3)	C18—H18C	0.9600
C7—C8	1.389 (3)	C19—H19A	0.9600
C7—C18	1.507 (3)	C19—H19B	0.9600
C8—C9	1.376 (3)	C19—H19C	0.9600
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.379 (3)	C20—H20B	0.9600
C9—C19	1.513 (3)	C20—H20C	0.9600
C10—C11	1.379 (3)	C21—H21A	0.9601
C10—H10	0.9300	C21—H21B	0.9601
C11—H11	0.9300	C21—H21C	0.9601
C12—C13	1.379 (3)
O1—C1—C2	121.6 (2)	C12—C13—H13	118.7
O1—C1—C4	121.5 (2)	C13—C14—C15	120.2 (2)
C2—C1—C4	116.9 (2)	C13—C14—H14	119.9
C3—C2—C1	123.4 (2)	C15—C14—H14	119.9
C3—C2—H2	118.3	C14—C15—C16	117.6 (2)
C1—C2—H2	118.3	C14—C15—C21	121.4 (2)
C2—C3—C12	126.7 (2)	C16—C15—C21	121.0 (2)
C2—C3—H3	116.6	C15—C16—C17	123.3 (2)
C12—C3—H3	116.7	C15—C16—H16	118.4
C5—C4—C1	123.1 (2)	C17—C16—H16	118.4
C5—C4—H4	118.4	C16—C17—C12	118.1 (2)
C1—C4—H4	118.4	C16—C17—C20	119.59 (19)
C4—C5—C6	126.8 (2)	C12—C17—C20	122.3 (2)
C4—C5—H5	116.6	C7—C18—H18A	109.5
C6—C5—H5	116.6	C7—C18—H18B	109.5
C11—C6—C7	118.4 (2)	H18A—C18—H18B	109.5
C11—C6—C5	120.2 (2)	C7—C18—H18C	109.5
C7—C6—C5	121.4 (2)	H18A—C18—H18C	109.5
C8—C7—C6	118.2 (2)	H18B—C18—H18C	109.5
C8—C7—C18	119.7 (2)	C9—C19—H19A	109.5
C6—C7—C18	122.09 (19)	C9—C19—H19B	109.5
C9—C8—C7	123.5 (2)	H19A—C19—H19B	109.5
C9—C8—H8	118.3	C9—C19—H19C	109.5
C7—C8—H8	118.3	H19A—C19—H19C	109.5
C8—C9—C10	117.5 (2)	H19B—C19—H19C	109.5
C8—C9—C19	121.9 (2)	C17—C20—H20A	109.5
C10—C9—C19	120.7 (2)	C17—C20—H20B	109.5
C11—C10—C9	120.8 (2)	H20A—C20—H20B	109.5
C11—C10—H10	119.6	C17—C20—H20C	109.5
C9—C10—H10	119.6	H20A—C20—H20C	109.5
C10—C11—C6	121.7 (2)	H20B—C20—H20C	109.5
C10—C11—H11	119.2	C15—C21—H21A	109.5
C6—C11—H11	119.1	C15—C21—H21B	109.5
C13—C12—C17	118.2 (2)	H21A—C21—H21B	109.5
C13—C12—C3	120.67 (19)	C15—C21—H21C	109.5
C17—C12—C3	121.08 (19)	H21A—C21—H21C	109.5
C14—C13—C12	122.6 (2)	H21B—C21—H21C	109.5
C14—C13—H13	118.7
O1—C1—C2—C3	−3.1 (3)	C9—C10—C11—C6	0.1 (4)
C4—C1—C2—C3	176.8 (2)	C7—C6—C11—C10	−0.8 (3)
C1—C2—C3—C12	177.8 (2)	C5—C6—C11—C10	177.5 (2)
O1—C1—C4—C5	1.1 (4)	C2—C3—C12—C13	−26.1 (3)
C2—C1—C4—C5	−178.8 (2)	C2—C3—C12—C17	154.2 (2)
C1—C4—C5—C6	−175.49 (19)	C17—C12—C13—C14	−0.5 (3)
C4—C5—C6—C11	24.6 (3)	C3—C12—C13—C14	179.7 (2)
C4—C5—C6—C7	−157.2 (2)	C12—C13—C14—C15	0.1 (4)
C11—C6—C7—C8	0.4 (3)	C13—C14—C15—C16	0.4 (4)
C5—C6—C7—C8	−177.83 (18)	C13—C14—C15—C21	−178.5 (2)
C11—C6—C7—C18	−178.7 (2)	C14—C15—C16—C17	−0.4 (3)
C5—C6—C7—C18	3.0 (3)	C21—C15—C16—C17	178.4 (2)
C6—C7—C8—C9	0.7 (3)	C15—C16—C17—C12	0.1 (3)
C18—C7—C8—C9	179.9 (2)	C15—C16—C17—C20	−178.8 (2)
C7—C8—C9—C10	−1.4 (3)	C13—C12—C17—C16	0.4 (3)
C7—C8—C9—C19	179.3 (2)	C3—C12—C17—C16	−179.83 (19)
C8—C9—C10—C11	1.0 (4)	C13—C12—C17—C20	179.2 (2)
C19—C9—C10—C11	−179.7 (2)	C3—C12—C17—C20	−1.0 (3)