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

The title compound, C(19)H(18)O, crystallizes in a non-centrosymmetric space group although the mol-ecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43 (13)°. The structure is stabilized by two intra-molecular hydrogen bonds, and by four π-π and three C-H⋯π inter-actions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the π-π inter-actions have values of 1.996, 2.061, 2.181 and 2.189 Å.

Related literature

For related literature, see: Butcher et al. (2006 ▶); Conard & Dolliver (1943 ▶); Harrison et al. (2006 ▶).

Experimental

Crystal data

C19H18O

M = 262.33

Monoclinic,

a = 19.937 (2) Å

b = 5.8637 (5) Å

c = 14.9207 (14) Å

β = 121.001 (3)°

V = 1495.1 (2) Å3

Z = 4

Mo Kα radiation radiation

μ = 0.07 mm−1

T = 296 (2) K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.988

9611 measured reflections

2288 independent reflections

1800 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.04

2288 reflections

183 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020084/bq2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020084/bq2087Isup2.hkl

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

C19H18O	F000 = 560
Mr = 262.33	Dx = 1.165 Mg m−3
Monoclinic, C2	Mo Kα radiation radiation λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3173 reflections
a = 19.937 (2) Å	θ = 2.1–29.6º
b = 5.8637 (5) Å	µ = 0.07 mm−1
c = 14.9207 (14) Å	T = 296 (2) K
β = 121.001 (3)º	Prism, yellow
V = 1495.1 (2) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2288 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
Detector resolution: 7.40 pixels mm-1	θmax = 29.6º
T = 296(2) K	θmin = 2.1º
ω scans	h = −26→27
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −8→4
Tmin = 0.980, Tmax = 0.988	l = −20→18
9611 measured reflections

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.4143P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2288 reflections	Δρmax = 0.22 e Å−3
183 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 726 Friedel pairs

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	0.49937 (12)	1.0189 (4)	0.63720 (18)	0.0745 (7)
C1	0.51762 (14)	0.8202 (5)	0.6423 (2)	0.0495 (6)
C2	0.59839 (13)	0.7416 (5)	0.71598 (18)	0.0470 (6)
H2	0.6115	0.5906	0.7132	0.056*
C3	0.65267 (13)	0.8809 (4)	0.78604 (17)	0.0429 (5)
H3	0.6374	1.0308	0.7861	0.051*
C4	0.73402 (12)	0.8232 (4)	0.86323 (17)	0.0383 (5)
C5	0.77901 (14)	0.9756 (4)	0.94391 (19)	0.0469 (5)
H5	0.7576	1.1150	0.9460	0.056*
C6	0.85484 (15)	0.9234 (5)	1.0209 (2)	0.0520 (6)
H6	0.8835	1.0278	1.0741	0.062*
C7	0.88884 (13)	0.7179 (5)	1.02006 (18)	0.0482 (6)
C8	0.84507 (14)	0.5688 (5)	0.9386 (2)	0.0523 (6)
H8	0.8672	0.4316	0.9355	0.063*
C9	0.76890 (13)	0.6194 (4)	0.86135 (18)	0.0459 (6)
H9	0.7407	0.5157	0.8076	0.055*
C10	0.97104 (15)	0.6567 (8)	1.1064 (2)	0.0751 (10)
H10A	0.9802	0.7163	1.1717	0.113*
H10B	1.0082	0.7211	1.0910	0.113*
H10C	0.9767	0.4938	1.1112	0.113*
C11	0.46029 (14)	0.6396 (4)	0.57787 (19)	0.0474 (6)
H11	0.4775	0.4907	0.5810	0.057*
C12	0.38539 (13)	0.6886 (5)	0.51634 (17)	0.0439 (5)
H12	0.3713	0.8398	0.5164	0.053*
C13	0.32183 (13)	0.5337 (4)	0.44805 (17)	0.0405 (5)
C14	0.33464 (13)	0.3184 (4)	0.41838 (19)	0.0447 (5)
H14	0.3856	0.2673	0.4444	0.054*
C15	0.27265 (14)	0.1824 (4)	0.35119 (18)	0.0444 (5)
H15	0.2822	0.0410	0.3318	0.053*
C16	0.19537 (14)	0.2537 (4)	0.31160 (18)	0.0432 (5)
C17	0.18269 (14)	0.4658 (4)	0.34177 (19)	0.0455 (5)
H17	0.1318	0.5159	0.3167	0.055*
C18	0.24460 (13)	0.6022 (4)	0.40822 (18)	0.0438 (5)
H18	0.2348	0.7438	0.4271	0.053*
C19	0.12788 (15)	0.1027 (5)	0.2395 (2)	0.0596 (7)
H19A	0.1447	−0.0047	0.2065	0.089*
H19B	0.0862	0.1944	0.1871	0.089*
H19C	0.1097	0.0220	0.2790	0.089*

	U11	U22	U33	U12	U13	U23
O1	0.0515 (11)	0.0599 (12)	0.0763 (14)	0.0052 (10)	0.0073 (10)	−0.0046 (11)
C1	0.0385 (12)	0.0582 (15)	0.0410 (13)	0.0011 (11)	0.0128 (10)	−0.0008 (12)
C2	0.0365 (11)	0.0545 (14)	0.0420 (12)	0.0027 (11)	0.0146 (10)	0.0004 (11)
C3	0.0392 (11)	0.0471 (12)	0.0406 (12)	0.0013 (11)	0.0194 (10)	0.0008 (10)
C4	0.0339 (10)	0.0444 (11)	0.0356 (11)	−0.0026 (9)	0.0171 (9)	0.0000 (10)
C5	0.0474 (13)	0.0427 (11)	0.0500 (13)	−0.0041 (10)	0.0247 (11)	−0.0086 (11)
C6	0.0436 (13)	0.0587 (15)	0.0446 (13)	−0.0127 (12)	0.0162 (11)	−0.0164 (12)
C7	0.0342 (11)	0.0621 (15)	0.0434 (13)	−0.0031 (11)	0.0164 (10)	0.0021 (13)
C8	0.0422 (12)	0.0522 (14)	0.0591 (15)	0.0055 (11)	0.0236 (11)	−0.0037 (13)
C9	0.0398 (12)	0.0466 (12)	0.0456 (13)	−0.0060 (10)	0.0179 (10)	−0.0144 (11)
C10	0.0380 (13)	0.098 (3)	0.0664 (18)	0.0033 (17)	0.0103 (13)	0.0052 (19)
C11	0.0432 (12)	0.0502 (13)	0.0443 (13)	0.0016 (11)	0.0193 (10)	0.0002 (11)
C12	0.0431 (12)	0.0469 (11)	0.0406 (12)	0.0004 (11)	0.0208 (10)	0.0016 (10)
C13	0.0415 (11)	0.0430 (11)	0.0341 (11)	−0.0038 (10)	0.0173 (9)	0.0034 (10)
C14	0.0403 (11)	0.0485 (12)	0.0451 (12)	0.0046 (10)	0.0219 (10)	0.0066 (11)
C15	0.0518 (13)	0.0388 (10)	0.0449 (12)	−0.0001 (10)	0.0265 (11)	0.0004 (10)
C16	0.0461 (12)	0.0426 (11)	0.0384 (11)	−0.0039 (10)	0.0201 (10)	0.0035 (9)
C17	0.0368 (11)	0.0469 (12)	0.0483 (13)	0.0041 (10)	0.0187 (10)	0.0076 (11)
C18	0.0445 (12)	0.0418 (11)	0.0459 (13)	0.0042 (10)	0.0238 (10)	0.0041 (10)
C19	0.0507 (14)	0.0595 (16)	0.0560 (15)	−0.0103 (13)	0.0185 (12)	−0.0065 (14)

O1—C1	1.211 (4)	C10—H10C	0.9600
C1—C2	1.480 (3)	C11—C12	1.320 (3)
C1—C11	1.490 (4)	C11—H11	0.9300
C2—C3	1.329 (3)	C12—C13	1.463 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.465 (3)	C13—C18	1.394 (3)
C3—H3	0.9300	C13—C14	1.404 (3)
C4—C9	1.390 (3)	C14—C15	1.375 (3)
C4—C5	1.393 (3)	C14—H14	0.9300
C5—C6	1.382 (4)	C15—C16	1.400 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.386 (4)	C16—C17	1.390 (3)
C6—H6	0.9300	C16—C19	1.503 (3)
C7—C8	1.383 (4)	C17—C18	1.373 (3)
C7—C10	1.516 (3)	C17—H17	0.9300
C8—C9	1.385 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—H10A	0.9600	C19—H19C	0.9600
C10—H10B	0.9600
O1—C1—C2	121.5 (3)	H10B—C10—H10C	109.5
O1—C1—C11	122.5 (2)	C12—C11—C1	120.7 (2)
C2—C1—C11	116.0 (2)	C12—C11—H11	119.6
C3—C2—C1	121.8 (2)	C1—C11—H11	119.6
C3—C2—H2	119.1	C11—C12—C13	127.8 (2)
C1—C2—H2	119.1	C11—C12—H12	116.1
C2—C3—C4	126.8 (2)	C13—C12—H12	116.1
C2—C3—H3	116.6	C18—C13—C14	117.7 (2)
C4—C3—H3	116.6	C18—C13—C12	119.2 (2)
C9—C4—C5	117.6 (2)	C14—C13—C12	123.0 (2)
C9—C4—C3	123.1 (2)	C15—C14—C13	120.7 (2)
C5—C4—C3	119.4 (2)	C15—C14—H14	119.7
C6—C5—C4	121.2 (2)	C13—C14—H14	119.7
C6—C5—H5	119.4	C14—C15—C16	121.0 (2)
C4—C5—H5	119.4	C14—C15—H15	119.5
C5—C6—C7	121.1 (2)	C16—C15—H15	119.5
C5—C6—H6	119.5	C17—C16—C15	118.3 (2)
C7—C6—H6	119.5	C17—C16—C19	120.9 (2)
C8—C7—C6	117.9 (2)	C15—C16—C19	120.7 (2)
C8—C7—C10	120.9 (3)	C18—C17—C16	120.6 (2)
C6—C7—C10	121.2 (3)	C18—C17—H17	119.7
C7—C8—C9	121.4 (3)	C16—C17—H17	119.7
C7—C8—H8	119.3	C17—C18—C13	121.7 (2)
C9—C8—H8	119.3	C17—C18—H18	119.2
C8—C9—C4	120.9 (2)	C13—C18—H18	119.2
C8—C9—H9	119.6	C16—C19—H19A	109.5
C4—C9—H9	119.6	C16—C19—H19B	109.5
C7—C10—H10A	109.5	H19A—C19—H19B	109.5
C7—C10—H10B	109.5	C16—C19—H19C	109.5
H10A—C10—H10B	109.5	H19A—C19—H19C	109.5
C7—C10—H10C	109.5	H19B—C19—H19C	109.5
H10A—C10—H10C	109.5
O1—C1—C2—C3	6.0 (4)	O1—C1—C11—C12	−4.0 (4)
C11—C1—C2—C3	−172.2 (2)	C2—C1—C11—C12	174.1 (2)
C1—C2—C3—C4	179.6 (2)	C1—C11—C12—C13	179.6 (2)
C2—C3—C4—C9	11.2 (4)	C11—C12—C13—C18	164.8 (2)
C2—C3—C4—C5	−167.6 (2)	C11—C12—C13—C14	−16.6 (4)
C9—C4—C5—C6	−1.7 (4)	C18—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	177.1 (2)	C12—C13—C14—C15	−177.9 (2)
C4—C5—C6—C7	0.4 (4)	C13—C14—C15—C16	−0.7 (3)
C5—C6—C7—C8	1.3 (4)	C14—C15—C16—C17	0.1 (3)
C5—C6—C7—C10	−177.9 (3)	C14—C15—C16—C19	−179.0 (2)
C6—C7—C8—C9	−1.6 (4)	C15—C16—C17—C18	0.4 (3)
C10—C7—C8—C9	177.6 (3)	C19—C16—C17—C18	179.5 (2)
C7—C8—C9—C4	0.2 (4)	C16—C17—C18—C13	−0.3 (3)
C5—C4—C9—C8	1.5 (4)	C14—C13—C18—C17	−0.3 (3)
C3—C4—C9—C8	−177.4 (2)	C12—C13—C18—C17	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.49	2.817 (4)	101
C12—H12···O1	0.93	2.48	2.819 (3)	102
C5—H5···CgAi	0.93	2.82	3.523 (3)	133
C9—H9···CgBii	0.93	2.89	3.604 (3)	134
C18—H18···CgBiii	0.93	2.95	3.621 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

CgA and CgB are the centroids of the C4–C9 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.93	2.49	2.817 (4)	101
C12—H12⋯O1	0.93	2.48	2.819 (3)	102
C5—H5⋯CgAi	0.93	2.82	3.523 (3)	133
C9—H9⋯CgBii	0.93	2.89	3.604 (3)	134
C18—H18⋯CgBiii	0.93	2.95	3.621 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) .