(E)-3-[4-(Dimethyl­amino)phen­yl]-1-(2-pyrid­yl)prop-2-en-1-one

Lin, S.; Jia, R.; Zhang, X.; Wang, Z.; Yuan, Y.

doi:10.1107/S1600536809015244

organic compounds

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Volume 65| Part 5| May 2009| Page o1161

doi:10.1107/S1600536809015244

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(E)-3-[4-(Dimethylamino)phenyl]-1-(2-pyridyl)prop-2-en-1-one

Songzhu Lin,^a ^* Ruokun Jia,^a Xiaojun Zhang,^a Zhiwen Wang ^a and Yanlin Yuan ^a

^aCollege of Chemical Engineering, Northest Dianli University, 132012 Jilin, People's Republic of China
^*Correspondence e-mail: Songzhulin@hotmail.com

(Received 7 April 2009; accepted 23 April 2009; online 30 April 2009)

In the title molecule, C₁₆H₁₆N₂O, 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 molecular structure is stabilized by intermolecular C—H⋯π and interactions.

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_r = 252.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.02
2619 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.10 e Å⁻³

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) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) x-1, y, z-1. Cg1 and Cg2 are the centroids of the pyridine and phenyl rings, respectively.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015244/hg2499sup1.cif

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

checkCIF report

Comment top

As an intermediate in the biosynthetic pathway of flavonoids, isoflavonoids, and aurone, chalcones have been shown to display a diverse array of phamacological activities, among which are antifungal, antibacterial, antiprotozoal, anti-inflammatory, antitumor, antimalarial, and anti-HIV activities (Zhao et al., 2007; Fichou et al., 1988; Butcher et al., 2007). In addition, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability (Sarojini et al., 2006). In order to research this kind of complex, we synthesis the title compound (I) and report its crystal structure (Fig. 1).

In the title molecule, C₁₆H₁₆N₂O, the pyridine ring and the atoms C6,C7,O1 are coplaner (p1), with the largest deviation of 0.045Å for O1. The dihedral angle between p1 and phenyl ring is 2.79 (2)°.

It is interesting to note that the molecular structure is stabilized by intermolecular C—H···π interactions and C—H···N intramolecular interactions (Table 1) [C_g(1) and C_g(2) refer to pyridine and phenyl ring, respectively].

Related literature top

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). Cg1 and Cg2 are the centroids of the pyridine and phenyl rings, respectively.

Experimental top

5 ml of 10% KOH solution was added to solution of 2-acetylpyridine (1.21 g, 0.01 mol) and 4-(dimethylamino)benzaldehyde (1.49 g, 0.01 mol) in 30 ml ethanol. The solution was stirred for 10 h and filtered. The product obtained was crystallized from acetone/toluene (1:1).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Sheldrick, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the c axis.

(E)-3-[4-(Dimethylamino)phenyl]-1-(2-pyridyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₆N₂O	F(000) = 536
M_r = 252.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.054P)² + 0.1706P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2619 reflections	Δρ_max = 0.13 e Å⁻³
175 parameters	Δρ_min = −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)

Crystal data top

C₁₆H₁₆N₂O	V = 1411.35 (16) Å³
M_r = 252.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1553 (4) Å	µ = 0.08 mm⁻¹
b = 17.4543 (12) Å	T = 295 K
c = 12.1087 (5) Å	0.25 × 0.20 × 0.18 mm
β = 125.032 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1608 reflections with I > 2σ(I)
7572 measured reflections	R_int = 0.026
2619 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
2619 reflections	Δρ_min = −0.10 e Å⁻³
175 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x+1, −y, −z; (iii) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O
M_r	252.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.1553 (4), 17.4543 (12), 12.1087 (5)
β (°)	125.032 (5)
V (Å³)	1411.35 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7572, 2619, 1608
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.02
No. of reflections	2619
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.10

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1	0.9300	2.5100	2.846 (2)	101.95
C8—H8A···O1	0.9300	2.5500	2.873 (2)	100.77
C10—H10A···Cg1ⁱ	0.9300	2.904	3.662	139.48
C15—H15B···Cg2ⁱⁱ	0.9600	3.202	3.870	128.22
C16—H16B···Cg1ⁱⁱⁱ	0.9600	3.173	3.908	134.62

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x+1, −y, −z; (iii) x−1, y, z−1.

References

Butcher, R. J., Jasinski, J. P., Narayana, B., Mayekar, A. N. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3546. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, 429–430. CrossRef Web of Science Google Scholar
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. J. (2006). J. Cryst. Growth, 295, 54–59. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Zhao, P. L., Liu, C. L., Huang, W., Wang, Y. Z. & Yang, G. F. (2007). J. Agric. Food Chem. 55, 5697–5700. Web of Science CrossRef PubMed CAS Google Scholar

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