(E)-3-[4-(Dimethyl-amino)phen-yl]-1-(4-methyl-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(19)NO, the dihedral angle between 4-methyl-phenyl and 4-(dimethyl-amino)phenyl rings is 45.5 (3)°. The C-C=C-C torsion angle of 173.8 (3)° indicates that the mol-ecule adopts an E configuration. The dimethyl-amino group is nearly coplanar with the attached benzene ring, making a dihedral angle of 2.7 (3)°. Weak inter-molecular C-H⋯π inter-actions are observed in the crystal structure.

Related literature

The title compound is a chalcone derivative; for the biological activiy of chalcones, see: Modzelewska et al. (2006 ▶); Opletalova & Sedivy (1999 ▶); Lin et al. (2002 ▶); Hsieh et al. (1998 ▶); Lunardi et al. (2003 ▶); Tang et al. (2008 ▶). For the organic non-linear optical properties of chalcones, see: Indira et al. (2002 ▶); Ravindra et al. (2009 ▶). For related structures, see: Wang et al. (2004 ▶); Yang et al. (2006 ▶).

Experimental

Crystal data

C18H19NO

M = 265.34

Orthorhombic,

a = 7.276 (2) Å

b = 11.567 (3) Å

c = 17.642 (5) Å

V = 1484.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 193 K

0.59 × 0.35 × 0.18 mm

Data collection

Rigaku Mercury diffractometer

16704 measured reflections

1958 independent reflections

1846 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.136

S = 1.31

1958 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052398/xu2690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052398/xu2690Isup2.hkl

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

C18H19NO	F(000) = 568
Mr = 265.34	Dx = 1.187 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: p 2ac 2ab	Cell parameters from 5334 reflections
a = 7.276 (2) Å	θ = 3.0–27.5°
b = 11.567 (3) Å	µ = 0.07 mm−1
c = 17.642 (5) Å	T = 193 K
V = 1484.8 (7) Å3	Block, yellow
Z = 4	0.59 × 0.35 × 0.18 mm

Rigaku Mercury diffractometer	1846 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
graphite	θmax = 27.5°, θmin = 3.0°
Detector resolution: 7.31 pixels mm-1	h = −9→9
ω scans	k = −14→14
16704 measured reflections	l = −19→22
1958 independent reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.31	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.3222P] where P = (Fo2 + 2Fc2)/3
1958 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 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	0.9451 (4)	0.62914 (17)	0.28002 (11)	0.0570 (7)
N1	1.0052 (4)	0.9449 (2)	−0.14961 (12)	0.0474 (7)
C1	0.9388 (4)	0.8121 (2)	0.07087 (15)	0.0340 (6)
C2	1.0071 (4)	0.9237 (2)	0.05857 (14)	0.0342 (6)
H2	1.0393	0.9701	0.1010	0.041*
C3	1.0288 (4)	0.9681 (2)	−0.01345 (15)	0.0355 (6)
H3	1.0754	1.0442	−0.0195	0.043*
C4	0.9833 (4)	0.9029 (2)	−0.07801 (15)	0.0361 (6)
C5	0.9100 (4)	0.7916 (2)	−0.06585 (15)	0.0389 (6)
H5	0.8734	0.7458	−0.1079	0.047*
C6	0.8909 (4)	0.7489 (3)	0.00638 (17)	0.0377 (6)
H6	0.8431	0.6732	0.0127	0.045*
C7	0.9790 (4)	0.7943 (2)	0.35669 (14)	0.0339 (6)
C8	1.0590 (4)	0.7345 (2)	0.41698 (16)	0.0395 (6)
H8	1.1025	0.6580	0.4094	0.047*
C9	1.0757 (4)	0.7849 (2)	0.48706 (16)	0.0424 (7)
H9	1.1343	0.7435	0.5268	0.051*
C10	1.0082 (4)	0.8956 (3)	0.50109 (15)	0.0399 (6)
C11	0.9305 (4)	0.9556 (3)	0.44122 (15)	0.0410 (7)
H11	0.8854	1.0317	0.4493	0.049*
C12	0.9174 (4)	0.9066 (2)	0.36960 (15)	0.0371 (6)
H12	0.8659	0.9499	0.3291	0.045*
C13	0.9252 (4)	0.7595 (2)	0.14493 (15)	0.0370 (6)
H13	0.8853	0.6813	0.1455	0.044*
C14	0.9611 (4)	0.8060 (2)	0.21291 (14)	0.0377 (6)
H14	0.9896	0.8860	0.2163	0.045*
C15	0.9573 (4)	0.7358 (2)	0.28210 (15)	0.0382 (6)
C16	1.0849 (5)	1.0576 (3)	−0.16376 (19)	0.0606 (9)
H16A	1.2040	1.0631	−0.1381	0.091*
H16B	1.0025	1.1177	−0.1444	0.091*
H16C	1.1022	1.0681	−0.2184	0.091*
C17	0.9558 (6)	0.8769 (3)	−0.21540 (16)	0.0685 (11)
H17A	0.8250	0.8568	−0.2129	0.103*
H17B	1.0294	0.8059	−0.2164	0.103*
H17C	0.9794	0.9218	−0.2615	0.103*
C18	1.0179 (5)	0.9481 (3)	0.57936 (17)	0.0571 (9)
H18A	0.9012	0.9352	0.6058	0.086*
H18B	1.0408	1.0314	0.5751	0.086*
H18C	1.1179	0.9119	0.6080	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0875 (18)	0.0342 (10)	0.0492 (12)	−0.0048 (12)	0.0013 (13)	0.0026 (9)
N1	0.0567 (17)	0.0519 (14)	0.0335 (12)	−0.0061 (14)	0.0025 (12)	0.0008 (11)
C1	0.0297 (12)	0.0345 (12)	0.0378 (13)	−0.0005 (12)	0.0019 (11)	−0.0026 (11)
C2	0.0345 (13)	0.0343 (13)	0.0339 (13)	0.0001 (12)	−0.0010 (12)	−0.0039 (11)
C3	0.0337 (14)	0.0334 (13)	0.0394 (14)	−0.0019 (11)	−0.0012 (12)	−0.0015 (11)
C4	0.0335 (13)	0.0400 (13)	0.0348 (13)	0.0043 (12)	−0.0008 (12)	−0.0008 (11)
C5	0.0375 (14)	0.0431 (14)	0.0360 (14)	−0.0043 (13)	−0.0030 (12)	−0.0099 (12)
C6	0.0354 (14)	0.0350 (12)	0.0426 (14)	−0.0062 (12)	−0.0010 (12)	−0.0056 (11)
C7	0.0297 (13)	0.0369 (13)	0.0351 (13)	−0.0004 (12)	0.0021 (11)	0.0058 (11)
C8	0.0390 (15)	0.0337 (12)	0.0458 (15)	−0.0025 (13)	0.0022 (13)	0.0076 (12)
C9	0.0421 (15)	0.0443 (15)	0.0409 (14)	−0.0033 (14)	−0.0048 (13)	0.0132 (12)
C10	0.0346 (14)	0.0496 (15)	0.0353 (13)	−0.0105 (13)	0.0030 (12)	0.0029 (12)
C11	0.0370 (14)	0.0441 (15)	0.0418 (15)	0.0014 (13)	0.0039 (13)	−0.0037 (12)
C12	0.0351 (14)	0.0385 (13)	0.0377 (14)	0.0056 (13)	−0.0015 (12)	0.0033 (12)
C13	0.0341 (14)	0.0352 (13)	0.0416 (14)	−0.0020 (12)	0.0035 (12)	0.0000 (11)
C14	0.0420 (15)	0.0344 (13)	0.0367 (14)	−0.0035 (13)	0.0011 (12)	0.0015 (11)
C15	0.0388 (14)	0.0365 (14)	0.0393 (14)	−0.0007 (12)	0.0034 (13)	−0.0003 (12)
C16	0.060 (2)	0.072 (2)	0.0499 (18)	−0.016 (2)	0.0025 (17)	0.0142 (16)
C17	0.086 (3)	0.085 (3)	0.0346 (16)	−0.017 (2)	0.0006 (19)	−0.0049 (16)
C18	0.063 (2)	0.074 (2)	0.0347 (14)	−0.017 (2)	0.0046 (16)	−0.0016 (15)

O1—C15	1.238 (3)	C9—C10	1.393 (4)
N1—C4	1.363 (3)	C9—H9	0.9500
N1—C17	1.448 (4)	C10—C11	1.385 (4)
N1—C16	1.448 (4)	C10—C18	1.510 (4)
C1—C6	1.396 (4)	C11—C12	1.388 (4)
C1—C2	1.400 (4)	C11—H11	0.9500
C1—C13	1.445 (4)	C12—H12	0.9500
C2—C3	1.380 (4)	C13—C14	1.340 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.405 (4)	C14—C15	1.466 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.410 (4)	C16—H16A	0.9800
C5—C6	1.374 (4)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C7—C12	1.393 (4)	C17—H17B	0.9800
C7—C8	1.396 (4)	C17—H17C	0.9800
C7—C15	1.488 (4)	C18—H18A	0.9800
C8—C9	1.372 (4)	C18—H18B	0.9800
C8—H8	0.9500	C18—H18C	0.9800
C4—N1—C17	121.4 (3)	C10—C11—C12	121.1 (3)
C4—N1—C16	121.8 (2)	C10—C11—H11	119.4
C17—N1—C16	116.8 (2)	C12—C11—H11	119.4
C6—C1—C2	116.4 (2)	C11—C12—C7	120.5 (3)
C6—C1—C13	120.0 (2)	C11—C12—H12	119.7
C2—C1—C13	123.6 (2)	C7—C12—H12	119.7
C3—C2—C1	121.8 (2)	C14—C13—C1	128.8 (2)
C3—C2—H2	119.1	C14—C13—H13	115.6
C1—C2—H2	119.1	C1—C13—H13	115.6
C2—C3—C4	121.3 (2)	C13—C14—C15	121.3 (2)
C2—C3—H3	119.3	C13—C14—H14	119.4
C4—C3—H3	119.3	C15—C14—H14	119.4
N1—C4—C3	122.2 (2)	O1—C15—C14	121.9 (2)
N1—C4—C5	120.7 (2)	O1—C15—C7	119.1 (2)
C3—C4—C5	117.1 (2)	C14—C15—C7	118.9 (2)
C6—C5—C4	120.5 (2)	N1—C16—H16A	109.5
C6—C5—H5	119.8	N1—C16—H16B	109.5
C4—C5—H5	119.8	H16A—C16—H16B	109.5
C5—C6—C1	122.9 (3)	N1—C16—H16C	109.5
C5—C6—H6	118.6	H16A—C16—H16C	109.5
C1—C6—H6	118.6	H16B—C16—H16C	109.5
C12—C7—C8	118.1 (2)	N1—C17—H17A	109.5
C12—C7—C15	122.3 (2)	N1—C17—H17B	109.5
C8—C7—C15	119.5 (2)	H17A—C17—H17B	109.5
C9—C8—C7	120.9 (2)	N1—C17—H17C	109.5
C9—C8—H8	119.6	H17A—C17—H17C	109.5
C7—C8—H8	119.6	H17B—C17—H17C	109.5
C8—C9—C10	121.3 (3)	C10—C18—H18A	109.5
C8—C9—H9	119.4	C10—C18—H18B	109.5
C10—C9—H9	119.4	H18A—C18—H18B	109.5
C11—C10—C9	118.0 (3)	C10—C18—H18C	109.5
C11—C10—C18	121.0 (3)	H18A—C18—H18C	109.5
C9—C10—C18	121.1 (3)	H18B—C18—H18C	109.5
C6—C1—C2—C3	−1.1 (4)	C8—C9—C10—C11	−2.7 (4)
C13—C1—C2—C3	175.8 (3)	C8—C9—C10—C18	176.7 (3)
C1—C2—C3—C4	−0.1 (4)	C9—C10—C11—C12	1.0 (4)
C17—N1—C4—C3	−179.3 (3)	C18—C10—C11—C12	−178.4 (3)
C16—N1—C4—C3	3.0 (4)	C10—C11—C12—C7	1.4 (4)
C17—N1—C4—C5	−0.5 (4)	C8—C7—C12—C11	−2.0 (4)
C16—N1—C4—C5	−178.3 (3)	C15—C7—C12—C11	176.2 (3)
C2—C3—C4—N1	−179.5 (3)	C6—C1—C13—C14	−178.7 (3)
C2—C3—C4—C5	1.7 (4)	C2—C1—C13—C14	4.6 (5)
N1—C4—C5—C6	179.0 (3)	C1—C13—C14—C15	−173.8 (3)
C3—C4—C5—C6	−2.2 (4)	C13—C14—C15—O1	9.7 (5)
C4—C5—C6—C1	1.1 (4)	C13—C14—C15—C7	−173.7 (3)
C2—C1—C6—C5	0.6 (4)	C12—C7—C15—O1	−151.9 (3)
C13—C1—C6—C5	−176.4 (3)	C8—C7—C15—O1	26.3 (4)
C12—C7—C8—C9	0.3 (4)	C12—C7—C15—C14	31.4 (4)
C15—C7—C8—C9	−178.0 (3)	C8—C7—C15—C14	−150.4 (3)
C7—C8—C9—C10	2.1 (4)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1i	0.95	2.94	3.697 (3)	138
C9—H9···Cg2ii	0.95	2.93	3.712 (3)	141
C16—H16B···Cg2iii	0.98	2.70	3.643 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1i	0.95	2.94	3.697 (3)	138
C9—H9⋯Cg2ii	0.95	2.93	3.712 (3)	141
C16—H16B⋯Cg2iii	0.98	2.70	3.643 (3)	161

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