(2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.

The title heteroaryl chalcone derivative, C(17)H(17)NO(4), is a condensation product of 2-acetyl-pyridine and 2,4,6-trimeth-oxy-benzaldehyde. The mol-ecule is roughly planar, the dihedral angle between the pyridine and benzene rings being 5.51 (10)°. All the three meth-oxy groups are almost co-planar with the bound benzene ring [r.m.s. deviation of 0.0306 (2) Å]. A weak C-H⋯O intra-molecular inter-action involving one of the ortho-meth-oxy groups generates an S(6) ring motif. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions into anti-parallel face-to-face pairs. Adjacent pairs are further connected into sheets parallel to the ab plane.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Fun et al. (2010 ▶, 2011 ▶). For background to and applications of chalcones and heteroaryl chalcones, see: Bandgar et al. (2010 ▶); Gacche et al. (2008 ▶); Go et al. (2005 ▶); Isomoto et al. (2005 ▶); Jung et al. (2008 ▶); Suwunwong et al. (2011 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C17H17NO4

M = 299.32

Orthorhombic,

a = 31.563 (2) Å

b = 44.508 (3) Å

c = 3.9504 (3) Å

V = 5549.6 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.58 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.943, T max = 0.996

31465 measured reflections

2309 independent reflections

1908 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.105

S = 1.09

2309 reflections

267 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536811039110/rz2642sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039110/rz2642Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039110/rz2642Isup3.cml

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

C17H17NO4	Dx = 1.433 Mg m−3
Mr = 299.32	Melting point = 392–393 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2309 reflections
a = 31.563 (2) Å	θ = 1.6–30.0°
b = 44.508 (3) Å	µ = 0.10 mm−1
c = 3.9504 (3) Å	T = 100 K
V = 5549.6 (7) Å3	Plate, pale yellow
Z = 16	0.58 × 0.14 × 0.04 mm
F(000) = 2528

Bruker APEXII CCD area detector diffractometer	2309 independent reflections
Radiation source: sealed tube	1908 reflections with I > 2σ(I)
graphite	Rint = 0.100
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −44→44
Tmin = 0.943, Tmax = 0.996	k = −62→62
31465 measured reflections	l = −5→5

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.0467P)2 + 4.8268P] where P = (Fo2 + 2Fc2)/3
2309 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.27 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 120.0 (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	0.18610 (5)	0.11217 (3)	1.2030 (5)	0.0298 (4)
O2	0.07115 (4)	0.04799 (3)	1.1758 (5)	0.0239 (3)
O3	0.05980 (4)	−0.04831 (3)	0.6752 (5)	0.0248 (4)
O4	0.19307 (4)	0.00496 (3)	0.6918 (5)	0.0242 (4)
N1	0.27419 (5)	0.08486 (4)	0.7393 (6)	0.0245 (4)
C1	0.31419 (7)	0.09271 (5)	0.6662 (7)	0.0263 (5)
C2	0.33299 (7)	0.11932 (5)	0.7701 (7)	0.0266 (5)
C3	0.30912 (7)	0.13912 (5)	0.9612 (7)	0.0270 (5)
C4	0.26779 (7)	0.13153 (5)	1.0406 (7)	0.0254 (5)
C5	0.25139 (6)	0.10419 (4)	0.9256 (7)	0.0225 (4)
C6	0.20685 (6)	0.09511 (4)	1.0251 (7)	0.0226 (4)
C7	0.19132 (7)	0.06578 (4)	0.9048 (7)	0.0228 (4)
C8	0.15391 (7)	0.05521 (4)	1.0129 (7)	0.0228 (4)
C9	0.13222 (6)	0.02737 (4)	0.9251 (6)	0.0213 (4)
C10	0.08883 (6)	0.02411 (4)	1.0100 (6)	0.0217 (4)
C11	0.06569 (6)	−0.00125 (4)	0.9267 (7)	0.0225 (4)
C12	0.08555 (6)	−0.02465 (4)	0.7554 (6)	0.0216 (4)
C13	0.12828 (6)	−0.02332 (4)	0.6760 (7)	0.0220 (4)
C14	0.15094 (6)	0.00253 (4)	0.7601 (6)	0.0217 (4)
C15	0.02726 (7)	0.04603 (5)	1.2600 (7)	0.0252 (5)
C16	0.07863 (7)	−0.07331 (5)	0.5027 (7)	0.0259 (5)
C17	0.21410 (7)	−0.02095 (5)	0.5537 (7)	0.0261 (5)
H1A	0.3305 (7)	0.0785 (5)	0.524 (8)	0.023 (6)*
H2A	0.3622 (7)	0.1239 (5)	0.708 (9)	0.027 (6)*
H3A	0.3216 (7)	0.1581 (5)	1.051 (8)	0.025 (6)*
H4A	0.2489 (7)	0.1445 (5)	1.187 (9)	0.030 (7)*
H8A	0.1375 (8)	0.0676 (6)	1.166 (9)	0.039 (8)*
H11A	0.0350 (7)	−0.0029 (5)	0.980 (8)	0.023 (6)*
H11B	0.2095 (7)	0.0554 (5)	0.747 (9)	0.025 (6)*
H13A	0.1415 (7)	−0.0402 (5)	0.545 (8)	0.025 (6)*
H15A	0.0101 (8)	0.0457 (6)	1.054 (9)	0.033 (8)*
H15B	0.0223 (8)	0.0281 (6)	1.428 (10)	0.038 (7)*
H15C	0.0194 (7)	0.0634 (5)	1.389 (8)	0.024 (7)*
H16A	0.0549 (7)	−0.0874 (5)	0.453 (8)	0.023 (6)*
H16B	0.0916 (7)	−0.0668 (5)	0.282 (9)	0.023 (6)*
H16C	0.1003 (8)	−0.0827 (5)	0.644 (9)	0.031 (7)*
H17A	0.2010 (8)	−0.0257 (6)	0.328 (9)	0.030 (8)*
H17B	0.2445 (7)	−0.0160 (5)	0.542 (8)	0.025 (6)*
H17C	0.2105 (7)	−0.0383 (5)	0.714 (9)	0.028 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0320 (8)	0.0216 (7)	0.0360 (11)	−0.0005 (6)	0.0043 (8)	−0.0058 (8)
O2	0.0246 (7)	0.0189 (6)	0.0283 (9)	0.0001 (5)	0.0026 (7)	−0.0024 (7)
O3	0.0251 (7)	0.0175 (6)	0.0317 (10)	−0.0026 (5)	0.0018 (7)	−0.0032 (7)
O4	0.0236 (7)	0.0194 (6)	0.0295 (10)	−0.0009 (5)	0.0026 (7)	−0.0034 (7)
N1	0.0284 (9)	0.0189 (8)	0.0264 (11)	0.0003 (6)	−0.0011 (8)	−0.0007 (8)
C1	0.0279 (10)	0.0233 (9)	0.0276 (13)	0.0008 (8)	0.0002 (10)	0.0019 (10)
C2	0.0290 (11)	0.0239 (9)	0.0270 (13)	−0.0012 (8)	−0.0014 (10)	0.0061 (10)
C3	0.0320 (11)	0.0203 (9)	0.0288 (14)	−0.0037 (8)	−0.0050 (11)	0.0023 (10)
C4	0.0313 (11)	0.0197 (9)	0.0251 (12)	−0.0004 (8)	−0.0021 (10)	0.0009 (9)
C5	0.0274 (10)	0.0188 (9)	0.0214 (11)	−0.0013 (7)	−0.0012 (9)	0.0033 (9)
C6	0.0267 (10)	0.0185 (9)	0.0224 (11)	0.0004 (7)	−0.0010 (9)	0.0029 (9)
C7	0.0278 (10)	0.0162 (9)	0.0242 (12)	0.0008 (7)	−0.0007 (9)	0.0012 (9)
C8	0.0266 (10)	0.0173 (8)	0.0245 (12)	0.0013 (7)	−0.0014 (9)	0.0017 (9)
C9	0.0258 (10)	0.0181 (9)	0.0200 (12)	0.0013 (7)	−0.0009 (9)	0.0019 (9)
C10	0.0287 (10)	0.0162 (8)	0.0201 (11)	0.0015 (7)	−0.0017 (9)	0.0011 (9)
C11	0.0233 (9)	0.0195 (9)	0.0248 (12)	0.0001 (7)	0.0002 (9)	0.0027 (9)
C12	0.0287 (10)	0.0156 (8)	0.0206 (12)	−0.0024 (7)	−0.0039 (9)	0.0021 (8)
C13	0.0263 (10)	0.0176 (8)	0.0220 (12)	−0.0009 (7)	−0.0012 (9)	−0.0009 (9)
C14	0.0245 (10)	0.0191 (9)	0.0214 (12)	0.0007 (7)	−0.0014 (9)	0.0028 (9)
C15	0.0247 (10)	0.0231 (9)	0.0279 (13)	0.0018 (8)	0.0003 (10)	−0.0022 (10)
C16	0.0305 (11)	0.0179 (9)	0.0292 (13)	−0.0016 (8)	−0.0011 (10)	−0.0026 (10)
C17	0.0264 (11)	0.0194 (9)	0.0325 (14)	0.0009 (8)	0.0045 (10)	−0.0029 (10)

O1—C6	1.224 (3)	C7—H11B	0.96 (3)
O2—C10	1.368 (2)	C8—C9	1.458 (3)
O2—C15	1.427 (3)	C8—H8A	0.97 (3)
O3—C12	1.367 (2)	C9—C14	1.413 (3)
O3—C16	1.434 (3)	C9—C10	1.417 (3)
O4—C14	1.361 (2)	C10—C11	1.384 (3)
O4—C17	1.438 (3)	C11—C12	1.392 (3)
N1—C5	1.341 (3)	C11—H11A	0.99 (2)
N1—C1	1.342 (3)	C12—C13	1.386 (3)
C1—C2	1.387 (3)	C13—C14	1.395 (3)
C1—H1A	0.99 (3)	C13—H13A	1.00 (3)
C2—C3	1.383 (3)	C15—H15A	0.98 (3)
C2—H2A	0.97 (2)	C15—H15B	1.05 (3)
C3—C4	1.384 (3)	C15—H15C	0.96 (3)
C3—H3A	1.00 (2)	C16—H16A	1.00 (2)
C4—C5	1.398 (3)	C16—H16B	1.01 (3)
C4—H4A	1.01 (3)	C16—H16C	0.98 (3)
C5—C6	1.515 (3)	C17—H17A	1.01 (3)
C6—C7	1.474 (3)	C17—H17B	0.99 (2)
C7—C8	1.341 (3)	C17—H17C	1.00 (3)
C10—O2—C15	117.39 (16)	O2—C10—C9	115.35 (17)
C12—O3—C16	117.48 (16)	C11—C10—C9	122.49 (19)
C14—O4—C17	117.55 (16)	C10—C11—C12	119.22 (19)
C5—N1—C1	117.13 (18)	C10—C11—H11A	121.7 (14)
N1—C1—C2	124.1 (2)	C12—C11—H11A	119.1 (14)
N1—C1—H1A	116.3 (13)	O3—C12—C13	123.98 (18)
C2—C1—H1A	119.5 (13)	O3—C12—C11	114.91 (18)
C3—C2—C1	118.2 (2)	C13—C12—C11	121.11 (18)
C3—C2—H2A	121.2 (15)	C12—C13—C14	118.69 (19)
C1—C2—H2A	120.6 (15)	C12—C13—H13A	119.3 (13)
C2—C3—C4	118.8 (2)	C14—C13—H13A	121.8 (13)
C2—C3—H3A	121.3 (14)	O4—C14—C13	121.27 (19)
C4—C3—H3A	119.8 (14)	O4—C14—C9	115.97 (17)
C3—C4—C5	119.2 (2)	C13—C14—C9	122.75 (18)
C3—C4—H4A	123.1 (13)	O2—C15—H15A	110.2 (17)
C5—C4—H4A	117.7 (13)	O2—C15—H15B	109.8 (14)
N1—C5—C4	122.54 (19)	H15A—C15—H15B	115 (2)
N1—C5—C6	117.99 (17)	O2—C15—H15C	109.0 (14)
C4—C5—C6	119.4 (2)	H15A—C15—H15C	108 (2)
O1—C6—C7	123.82 (19)	H15B—C15—H15C	104 (2)
O1—C6—C5	118.70 (18)	O3—C16—H16A	105.8 (14)
C7—C6—C5	117.47 (19)	O3—C16—H16B	111.0 (14)
C8—C7—C6	120.1 (2)	H16A—C16—H16B	108 (2)
C8—C7—H11B	124.1 (14)	O3—C16—H16C	110.5 (17)
C6—C7—H11B	115.8 (14)	H16A—C16—H16C	112 (2)
C7—C8—C9	129.5 (2)	H16B—C16—H16C	109 (2)
C7—C8—H8A	118.2 (15)	O4—C17—H17A	108.4 (15)
C9—C8—H8A	112.3 (15)	O4—C17—H17B	106.7 (14)
C14—C9—C10	115.68 (17)	H17A—C17—H17B	114 (2)
C14—C9—C8	125.35 (18)	O4—C17—H17C	109.0 (16)
C10—C9—C8	118.97 (18)	H17A—C17—H17C	111 (2)
O2—C10—C11	122.16 (18)	H17B—C17—H17C	108 (2)
C5—N1—C1—C2	−0.2 (4)	C8—C9—C10—O2	−1.0 (3)
N1—C1—C2—C3	0.0 (4)	C14—C9—C10—C11	−2.2 (3)
C1—C2—C3—C4	0.1 (4)	C8—C9—C10—C11	178.1 (2)
C2—C3—C4—C5	−0.1 (4)	O2—C10—C11—C12	179.5 (2)
C1—N1—C5—C4	0.3 (3)	C9—C10—C11—C12	0.5 (4)
C1—N1—C5—C6	−177.1 (2)	C16—O3—C12—C13	0.9 (3)
C3—C4—C5—N1	−0.1 (4)	C16—O3—C12—C11	−179.1 (2)
C3—C4—C5—C6	177.2 (2)	C10—C11—C12—O3	−178.1 (2)
N1—C5—C6—O1	178.0 (2)	C10—C11—C12—C13	1.9 (4)
C4—C5—C6—O1	0.5 (3)	O3—C12—C13—C14	177.6 (2)
N1—C5—C6—C7	−1.1 (3)	C11—C12—C13—C14	−2.3 (3)
C4—C5—C6—C7	−178.5 (2)	C17—O4—C14—C13	−4.7 (3)
O1—C6—C7—C8	−5.8 (4)	C17—O4—C14—C9	174.2 (2)
C5—C6—C7—C8	173.2 (2)	C12—C13—C14—O4	179.2 (2)
C6—C7—C8—C9	179.0 (2)	C12—C13—C14—C9	0.4 (3)
C7—C8—C9—C14	14.7 (4)	C10—C9—C14—O4	−177.1 (2)
C7—C8—C9—C10	−165.6 (2)	C8—C9—C14—O4	2.6 (3)
C15—O2—C10—C11	−0.4 (3)	C10—C9—C14—C13	1.8 (3)
C15—O2—C10—C9	178.7 (2)	C8—C9—C14—C13	−178.6 (2)
C14—C9—C10—O2	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B···O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B···O4ii	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	1.00 (2)	2.45 (3)	3.369 (2)	157.8 (17)
C7—H11B⋯O4	0.97 (3)	2.31 (2)	2.835 (2)	113.1 (18)
C17—H17B⋯O4ii	0.99 (2)	2.46 (2)	3.337 (3)	148 (2)

Symmetry codes: (i) ; (ii) .