(E)-1-(4-Amino-phen-yl)-3-(pyridin-3-yl)prop-2-en-1-one.

The title chalcone derivative, C(14)H(12)N(2)O, consists of 4-amino-phenyl and pyridine rings bridged by a prop-2-en-1-one unit and exists in a trans configuration with respect to the C=C double bond. The mol-ecule is slightly twisted with a dihedral angle of 29.38 (7)° between the benzene and pyridine rings. The prop-2-en-1-one bridge is nearly planar with an r.m.s. deviation of 0.0384 (1) Å and makes dihedral angles of 15.40 (9) and 16.30 (9)°, respectively, with the benzene and pyridine rings. In the crystal, mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds into a layer parallel to the ab plane. A π-π inter-action with a centroid-centroid distance of 3.6946 (10) Å is also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Horkaew et al. (2010 ▶). For background to and applications of chalcones, see: Gaber et al. (2008 ▶); Ávila et al. (2008 ▶); Mei et al. (2001 ▶); Ohad et al. (2004 ▶); Patil et al. (2007 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶); Wu et al. (2006 ▶); Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H12N2O

M = 224.26

Orthorhombic,

a = 12.0046 (12) Å

b = 7.9329 (9) Å

c = 22.925 (3) Å

V = 2183.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.52 × 0.32 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.956, T max = 0.985

12726 measured reflections

3177 independent reflections

2433 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.03

3177 reflections

202 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023634/is2731sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023634/is2731Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023634/is2731Isup3.cml

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

C14H12N2O	Dx = 1.365 Mg m−3
Mr = 224.26	Melting point = 453–454 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3177 reflections
a = 12.0046 (12) Å	θ = 2.5–30.0°
b = 7.9329 (9) Å	µ = 0.09 mm−1
c = 22.925 (3) Å	T = 100 K
V = 2183.2 (4) Å3	Block, yellow
Z = 8	0.52 × 0.32 × 0.18 mm
F(000) = 944

Bruker APEX DUO CCD area-detector diffractometer	3177 independent reflections
Radiation source: sealed tube	2433 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→14
Tmin = 0.956, Tmax = 0.985	k = −11→10
12726 measured reflections	l = −32→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.5761P] where P = (Fo2 + 2Fc2)/3
3177 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.87481 (8)	−0.00829 (13)	0.62116 (4)	0.0274 (2)
N1	0.88749 (10)	−0.40307 (16)	0.86417 (5)	0.0262 (3)
H1N1	0.9537 (17)	−0.447 (3)	0.8695 (9)	0.037 (5)*
H2N1	0.8278 (17)	−0.431 (3)	0.8878 (9)	0.043 (5)*
N2	0.34284 (10)	0.06758 (18)	0.57106 (5)	0.0317 (3)
C1	0.82037 (9)	−0.14511 (16)	0.70829 (6)	0.0195 (3)
C2	0.92774 (10)	−0.20798 (16)	0.72041 (6)	0.0210 (3)
H2A	0.9864 (14)	−0.193 (2)	0.6922 (7)	0.023 (4)*
C3	0.95058 (10)	−0.29288 (16)	0.77139 (6)	0.0214 (3)
H3A	1.0254 (14)	−0.340 (2)	0.7786 (7)	0.029 (4)*
C4	0.86642 (10)	−0.31820 (17)	0.81357 (6)	0.0208 (3)
C5	0.75956 (10)	−0.25227 (18)	0.80220 (6)	0.0234 (3)
H5A	0.7024 (17)	−0.265 (3)	0.8321 (9)	0.045 (5)*
C6	0.73797 (10)	−0.16943 (17)	0.75074 (6)	0.0214 (3)
H6A	0.6624 (14)	−0.121 (2)	0.7442 (7)	0.025 (4)*
C7	0.79831 (10)	−0.05897 (16)	0.65285 (6)	0.0205 (3)
C8	0.68037 (10)	−0.03488 (18)	0.63425 (6)	0.0226 (3)
H8A	0.6213 (16)	−0.097 (3)	0.6564 (9)	0.042 (5)*
C9	0.65435 (10)	0.06655 (17)	0.58997 (6)	0.0232 (3)
H9A	0.7163 (14)	0.126 (2)	0.5705 (7)	0.031 (4)*
C10	0.54235 (10)	0.10884 (17)	0.56899 (6)	0.0219 (3)
C11	0.52786 (11)	0.2397 (2)	0.52922 (6)	0.0284 (3)
H11A	0.5968 (15)	0.303 (2)	0.5147 (8)	0.030 (4)*
C12	0.42183 (12)	0.2841 (2)	0.51084 (7)	0.0313 (3)
H12A	0.4105 (16)	0.374 (3)	0.4827 (9)	0.040 (5)*
C13	0.33284 (12)	0.1966 (2)	0.53375 (7)	0.0313 (3)
H13A	0.2553 (16)	0.229 (2)	0.5245 (8)	0.041 (5)*
C14	0.44619 (11)	0.0255 (2)	0.58784 (6)	0.0267 (3)
H14A	0.4500 (15)	−0.070 (3)	0.6168 (8)	0.034 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0178 (4)	0.0354 (6)	0.0292 (5)	−0.0004 (4)	0.0009 (4)	0.0037 (4)
N1	0.0177 (5)	0.0342 (7)	0.0267 (6)	0.0028 (4)	−0.0018 (4)	0.0020 (5)
N2	0.0186 (5)	0.0466 (8)	0.0299 (6)	−0.0020 (5)	−0.0015 (5)	0.0051 (5)
C1	0.0148 (5)	0.0193 (6)	0.0245 (6)	0.0002 (4)	−0.0024 (4)	−0.0034 (5)
C2	0.0143 (5)	0.0216 (6)	0.0271 (6)	−0.0001 (4)	0.0004 (5)	−0.0027 (5)
C3	0.0135 (5)	0.0219 (6)	0.0286 (7)	0.0010 (4)	−0.0020 (4)	−0.0031 (5)
C4	0.0169 (5)	0.0219 (6)	0.0237 (6)	0.0004 (4)	−0.0026 (4)	−0.0043 (5)
C5	0.0156 (5)	0.0296 (7)	0.0248 (6)	0.0029 (5)	0.0011 (5)	−0.0027 (5)
C6	0.0142 (5)	0.0243 (6)	0.0255 (6)	0.0023 (4)	−0.0015 (4)	−0.0051 (5)
C7	0.0158 (5)	0.0210 (6)	0.0246 (6)	0.0004 (4)	−0.0013 (4)	−0.0038 (5)
C8	0.0159 (5)	0.0263 (7)	0.0257 (6)	−0.0015 (5)	−0.0013 (5)	−0.0001 (5)
C9	0.0162 (5)	0.0267 (7)	0.0267 (6)	0.0002 (5)	0.0014 (5)	−0.0009 (5)
C10	0.0186 (6)	0.0265 (7)	0.0205 (6)	0.0019 (4)	−0.0003 (4)	−0.0019 (5)
C11	0.0214 (6)	0.0339 (8)	0.0298 (7)	0.0001 (5)	0.0019 (5)	0.0049 (6)
C12	0.0264 (7)	0.0358 (8)	0.0316 (7)	0.0036 (5)	−0.0038 (6)	0.0071 (6)
C13	0.0210 (6)	0.0440 (9)	0.0290 (7)	0.0039 (6)	−0.0043 (5)	0.0027 (6)
C14	0.0190 (6)	0.0348 (8)	0.0262 (7)	−0.0019 (5)	−0.0015 (5)	0.0039 (6)

O1—C7	1.2381 (16)	C5—H5A	0.97 (2)
N1—C4	1.3649 (18)	C6—H6A	0.996 (17)
N1—H1N1	0.88 (2)	C7—C8	1.4909 (17)
N1—H2N1	0.93 (2)	C8—C9	1.332 (2)
N2—C13	1.339 (2)	C8—H8A	1.00 (2)
N2—C14	1.3410 (17)	C9—C10	1.4668 (17)
C1—C6	1.4011 (18)	C9—H9A	0.986 (18)
C1—C2	1.4097 (16)	C10—C11	1.392 (2)
C1—C7	1.4671 (18)	C10—C14	1.3986 (19)
C2—C3	1.3767 (19)	C11—C12	1.3864 (19)
C2—H2A	0.963 (16)	C11—H11A	1.023 (18)
C3—C4	1.4127 (18)	C12—C13	1.378 (2)
C3—H3A	0.988 (17)	C12—H12A	0.97 (2)
C4—C5	1.4097 (17)	C13—H13A	0.99 (2)
C5—C6	1.3749 (19)	C14—H14A	1.01 (2)
C4—N1—H1N1	118.9 (13)	O1—C7—C8	119.67 (12)
C4—N1—H2N1	118.2 (12)	C1—C7—C8	118.61 (11)
H1N1—N1—H2N1	121.7 (19)	C9—C8—C7	121.19 (12)
C13—N2—C14	117.14 (13)	C9—C8—H8A	121.1 (11)
C6—C1—C2	117.38 (12)	C7—C8—H8A	117.8 (11)
C6—C1—C7	122.58 (11)	C8—C9—C10	127.07 (12)
C2—C1—C7	120.04 (11)	C8—C9—H9A	117.1 (10)
C3—C2—C1	121.50 (12)	C10—C9—H9A	115.8 (10)
C3—C2—H2A	119.0 (10)	C11—C10—C14	116.83 (12)
C1—C2—H2A	119.5 (10)	C11—C10—C9	119.98 (12)
C2—C3—C4	120.55 (11)	C14—C10—C9	123.18 (12)
C2—C3—H3A	120.7 (10)	C12—C11—C10	120.21 (13)
C4—C3—H3A	118.8 (10)	C12—C11—H11A	121.3 (10)
N1—C4—C5	120.58 (12)	C10—C11—H11A	118.5 (10)
N1—C4—C3	121.28 (11)	C13—C12—C11	117.90 (14)
C5—C4—C3	118.13 (12)	C13—C12—H12A	121.0 (12)
C6—C5—C4	120.50 (12)	C11—C12—H12A	121.1 (12)
C6—C5—H5A	121.3 (12)	N2—C13—C12	123.98 (13)
C4—C5—H5A	118.2 (12)	N2—C13—H13A	115.0 (11)
C5—C6—C1	121.92 (11)	C12—C13—H13A	121.0 (11)
C5—C6—H6A	119.0 (10)	N2—C14—C10	123.89 (14)
C1—C6—H6A	119.0 (10)	N2—C14—H14A	114.7 (10)
O1—C7—C1	121.71 (11)	C10—C14—H14A	121.4 (10)
C6—C1—C2—C3	1.23 (18)	O1—C7—C8—C9	−12.5 (2)
C7—C1—C2—C3	−178.45 (12)	C1—C7—C8—C9	168.37 (12)
C1—C2—C3—C4	−0.56 (19)	C7—C8—C9—C10	−176.57 (13)
C2—C3—C4—N1	179.56 (12)	C8—C9—C10—C11	168.40 (14)
C2—C3—C4—C5	−0.85 (19)	C8—C9—C10—C14	−10.3 (2)
N1—C4—C5—C6	−178.84 (13)	C14—C10—C11—C12	1.1 (2)
C3—C4—C5—C6	1.57 (19)	C9—C10—C11—C12	−177.71 (14)
C4—C5—C6—C1	−0.9 (2)	C10—C11—C12—C13	0.9 (2)
C2—C1—C6—C5	−0.50 (19)	C14—N2—C13—C12	1.8 (2)
C7—C1—C6—C5	179.18 (12)	C11—C12—C13—N2	−2.5 (2)
C6—C1—C7—O1	165.18 (12)	C13—N2—C14—C10	0.5 (2)
C2—C1—C7—O1	−15.15 (19)	C11—C10—C14—N2	−1.9 (2)
C6—C1—C7—C8	−15.74 (19)	C9—C10—C14—N2	176.92 (14)
C2—C1—C7—C8	163.92 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.88 (2)	2.13 (2)	2.9920 (16)	170 (2)
N1—H2N1···N2ii	0.93 (2)	2.26 (2)	3.1471 (17)	161.7 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.88 (2)	2.13 (2)	2.9920 (16)	170 (2)
N1—H2N1⋯N2ii	0.93 (2)	2.26 (2)	3.1471 (17)	161.7 (19)

Symmetry codes: (i) ; (ii) .