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

In the title mol-ecule, C(16)H(16)N(2)O, the pyridine ring and non-H atoms of the =CH-C(=O)- unit are coplaner, the largest deviation being 0.045 (2) Å for the O atom. The dihedral angle between this plane and the benzene ring is 2.79 (2)°. The mol-ecular structure is stabilized by inter-molecular C-H⋯π and inter-actions.

Related literature

For a related structure, see: Butcher et al. (2007 ▶). For the phamacological activity of chalcones, see: Zhao et al. (2007 ▶); Fichou et al. (1988 ▶). For the blue-light transmittance of chalcone derivatives, see: Sarojini et al. (2006 ▶).

Experimental

Crystal data

C16H16N2O

M = 252.31

Monoclinic,

a = 8.1553 (4) Å

b = 17.4543 (12) Å

c = 12.1087 (5) Å

β = 125.032 (5)°

V = 1411.35 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

7572 measured reflections

2619 independent reflections

1608 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.02

2619 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.10 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809015244/hg2499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015244/hg2499Isup2.hkl

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

C16H16N2O	F(000) = 536
Mr = 252.31	Dx = 1.187 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2y bc	Cell parameters from 1586 reflections
a = 8.1553 (4) Å	θ = 2.0–25.4°
b = 17.4543 (12) Å	µ = 0.08 mm−1
c = 12.1087 (5) Å	T = 295 K
β = 125.032 (5)°	Block, red
V = 1411.35 (16) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1608 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.5°, θmin = 2.3°
φ and ω scans	h = −6→9
7572 measured reflections	k = −21→20
2619 independent reflections	l = −14→14

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.054P)2 + 0.1706P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2619 reflections	Δρmax = 0.13 e Å−3
175 parameters	Δρmin = −0.10 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (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	0.3917 (2)	0.59831 (8)	−0.12014 (13)	0.0974 (5)
N1	0.1005 (2)	0.75477 (9)	−0.13939 (15)	0.0741 (4)
N2	0.7635 (3)	0.56873 (11)	0.70210 (17)	0.0942 (6)
C1	−0.0344 (3)	0.80574 (12)	−0.2313 (2)	0.0888 (6)
H1A	−0.0832	0.8425	−0.2015	0.107*
C2	−0.1059 (3)	0.80743 (13)	−0.3672 (2)	0.0873 (6)
H2A	−0.1993	0.8438	−0.4256	0.105*
C3	−0.0344 (3)	0.75393 (13)	−0.41174 (19)	0.0831 (6)
H3A	−0.0778	0.7532	−0.5015	0.100*
C4	0.1047 (3)	0.70057 (11)	−0.32047 (18)	0.0717 (5)
H4A	0.1552	0.6637	−0.3489	0.086*
C5	0.1685 (2)	0.70242 (9)	−0.18518 (17)	0.0606 (4)
C6	0.3188 (3)	0.64457 (10)	−0.08317 (17)	0.0665 (5)
C7	0.3733 (3)	0.64595 (10)	0.05562 (17)	0.0662 (5)
H7A	0.3199	0.6844	0.0793	0.079*
C8	0.4975 (3)	0.59389 (9)	0.15074 (17)	0.0644 (5)
H8A	0.5468	0.5563	0.1227	0.077*
C9	0.5646 (2)	0.58887 (9)	0.29150 (16)	0.0598 (4)
C10	0.4985 (3)	0.63890 (10)	0.34847 (18)	0.0723 (5)
H10A	0.4098	0.6779	0.2955	0.087*
C11	0.5612 (3)	0.63226 (11)	0.48151 (19)	0.0784 (6)
H11A	0.5121	0.6666	0.5146	0.094*
C12	0.6978 (3)	0.57483 (11)	0.56871 (18)	0.0704 (5)
C13	0.7654 (3)	0.52452 (11)	0.51256 (18)	0.0728 (5)
H13A	0.8554	0.4859	0.5656	0.087*
C14	0.6996 (3)	0.53165 (10)	0.37868 (18)	0.0680 (5)
H14A	0.7470	0.4970	0.3449	0.082*
C15	0.9044 (4)	0.50919 (15)	0.7917 (2)	0.1197 (9)
H15A	1.0236	0.5121	0.7937	0.180*
H15B	0.8437	0.4597	0.7591	0.180*
H15C	0.9381	0.5167	0.8811	0.180*
C16	0.6813 (4)	0.61785 (15)	0.7560 (2)	0.1247 (10)
H16A	0.5384	0.6120	0.7031	0.187*
H16B	0.7140	0.6703	0.7528	0.187*
H16C	0.7371	0.6037	0.8478	0.187*

	U11	U22	U33	U12	U13	U23
O1	0.1348 (12)	0.0967 (10)	0.0907 (10)	0.0326 (9)	0.0822 (10)	0.0081 (8)
N1	0.0852 (11)	0.0825 (10)	0.0739 (10)	0.0124 (9)	0.0569 (9)	0.0096 (8)
N2	0.1095 (14)	0.1125 (14)	0.0666 (11)	−0.0230 (11)	0.0540 (10)	−0.0111 (10)
C1	0.1010 (15)	0.0973 (15)	0.0916 (14)	0.0264 (13)	0.0690 (13)	0.0204 (12)
C2	0.0818 (14)	0.1094 (16)	0.0779 (13)	0.0158 (12)	0.0500 (12)	0.0254 (12)
C3	0.0809 (13)	0.1099 (16)	0.0624 (11)	−0.0060 (12)	0.0433 (11)	0.0071 (11)
C4	0.0804 (13)	0.0803 (12)	0.0680 (12)	−0.0099 (10)	0.0506 (10)	−0.0070 (10)
C5	0.0655 (10)	0.0652 (10)	0.0655 (10)	−0.0091 (9)	0.0459 (9)	−0.0026 (8)
C6	0.0782 (12)	0.0663 (10)	0.0724 (11)	−0.0016 (9)	0.0534 (10)	−0.0032 (9)
C7	0.0756 (11)	0.0681 (11)	0.0684 (11)	0.0040 (9)	0.0491 (10)	−0.0014 (9)
C8	0.0711 (11)	0.0635 (10)	0.0718 (11)	−0.0008 (9)	0.0488 (10)	−0.0052 (9)
C9	0.0618 (10)	0.0621 (10)	0.0624 (10)	−0.0032 (8)	0.0398 (9)	−0.0043 (8)
C10	0.0753 (12)	0.0755 (12)	0.0694 (12)	0.0078 (9)	0.0434 (10)	−0.0048 (9)
C11	0.0841 (13)	0.0875 (13)	0.0743 (13)	−0.0014 (11)	0.0517 (11)	−0.0168 (11)
C12	0.0712 (12)	0.0834 (13)	0.0610 (11)	−0.0225 (10)	0.0404 (10)	−0.0124 (9)
C13	0.0752 (12)	0.0774 (12)	0.0690 (12)	0.0005 (10)	0.0431 (10)	0.0051 (9)
C14	0.0734 (12)	0.0678 (11)	0.0743 (12)	0.0026 (9)	0.0492 (10)	−0.0012 (9)
C15	0.122 (2)	0.150 (2)	0.0671 (14)	−0.0307 (18)	0.0424 (14)	0.0099 (15)
C16	0.170 (2)	0.141 (2)	0.0992 (17)	−0.0506 (19)	0.0988 (18)	−0.0452 (16)

O1—C6	1.2293 (19)	C8—C9	1.463 (2)
N1—C5	1.343 (2)	C8—H8A	0.9300
N1—C1	1.355 (2)	C9—C10	1.398 (2)
N2—C12	1.383 (2)	C9—C14	1.411 (2)
N2—C16	1.454 (3)	C10—C11	1.387 (2)
N2—C15	1.465 (3)	C10—H10A	0.9300
C1—C2	1.396 (3)	C11—C12	1.418 (3)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.365 (3)	C12—C13	1.403 (2)
C2—H2A	0.9300	C13—C14	1.390 (2)
C3—C4	1.391 (3)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.406 (2)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.520 (2)	C15—H15C	0.9600
C6—C7	1.472 (2)	C16—H16A	0.9600
C7—C8	1.356 (2)	C16—H16B	0.9600
C7—H7A	0.9300	C16—H16C	0.9600
C5—N1—C1	116.17 (16)	C10—C9—C8	123.02 (16)
C12—N2—C16	120.7 (2)	C14—C9—C8	121.56 (15)
C12—N2—C15	122.19 (19)	C11—C10—C9	122.09 (17)
C16—N2—C15	116.96 (19)	C11—C10—H10A	119.0
N1—C1—C2	125.10 (19)	C9—C10—H10A	119.0
N1—C1—H1A	117.4	C10—C11—C12	122.16 (17)
C2—C1—H1A	117.4	C10—C11—H11A	118.9
C3—C2—C1	117.86 (19)	C12—C11—H11A	118.9
C3—C2—H2A	121.1	N2—C12—C13	121.42 (19)
C1—C2—H2A	121.1	N2—C12—C11	122.41 (18)
C2—C3—C4	118.83 (18)	C13—C12—C11	116.17 (16)
C2—C3—H3A	120.6	C14—C13—C12	120.88 (18)
C4—C3—H3A	120.6	C14—C13—H13A	119.6
C3—C4—C5	119.88 (17)	C12—C13—H13A	119.6
C3—C4—H4A	120.1	C13—C14—C9	123.30 (16)
C5—C4—H4A	120.1	C13—C14—H14A	118.4
N1—C5—C4	122.16 (17)	C9—C14—H14A	118.4
N1—C5—C6	116.63 (15)	N2—C15—H15A	109.5
C4—C5—C6	121.22 (15)	N2—C15—H15B	109.5
O1—C6—C7	122.33 (17)	H15A—C15—H15B	109.5
O1—C6—C5	118.26 (15)	N2—C15—H15C	109.5
C7—C6—C5	119.41 (15)	H15A—C15—H15C	109.5
C8—C7—C6	123.19 (16)	H15B—C15—H15C	109.5
C8—C7—H7A	118.4	N2—C16—H16A	109.5
C6—C7—H7A	118.4	N2—C16—H16B	109.5
C7—C8—C9	128.81 (16)	H16A—C16—H16B	109.5
C7—C8—H8A	115.6	N2—C16—H16C	109.5
C9—C8—H8A	115.6	H16A—C16—H16C	109.5
C10—C9—C14	115.41 (15)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1	0.93	2.51	2.846 (2)	102
C8—H8A···O1	0.93	2.55	2.873 (2)	101
C10—H10A···Cg1i	0.93	2.90	3.662	140
C15—H15B···Cg2ii	0.96	3.20	3.870	128
C16—H16B···Cg1iii	0.96	3.17	3.908	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg1i	0.93	2.90	3.662	139
C15—H15B⋯Cg2ii	0.96	3.20	3.870	128
C16—H16B⋯Cg1iii	0.96	3.17	3.908	135

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the pyridine and phenyl rings, respectively.