(2E)-1-(Pyridin-2-yl)-3-(2,4,5-tri-meth-oxy-phen-yl)prop-2-en-1-one.

The title heteroaryl chalcone derivative, C17H17NO4, is close to planar: the dihedral angle between the pyridine and benzene rings is 3.71 (11)° and the meth-oxy C atoms deviate from their attached ring by 0.046 (3), -0.044 (2) and 0.127 (3) Å. The disposition of the pyridine N atom and the carbonyl group is anti [N-C-C-O = -177.7 (2)°]. In the crystal, mol-ecules are linked by weak C-H⋯N and C-H⋯O inter-actions into (100) sheets and an aromatic π-π stacking inter-action between the pyridine and benzene ring, with a centroid-centroid separation of 3.7036 (14) Å also occurs.

Related literature

For the fluorescence properties of heteroaryl chalcones, see: Suwunwong et al. (2011 ▶). For related structures, see: Chantrapromma et al. (2009 ▶); Fun et al. (2010 ▶, 2011 ▶); Suwunwong et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H17NO4

M = 299.32

Monoclinic,

a = 8.4047 (3) Å

b = 8.7285 (3) Å

c = 19.5086 (7) Å

β = 94.113 (2)°

V = 1427.47 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.32 × 0.27 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.969, T max = 0.984

14970 measured reflections

3792 independent reflections

2435 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.188

S = 1.07

3792 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.29 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015821/hb7090sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015821/hb7090Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015821/hb7090Isup3.cml

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

C17H17NO4	F(000) = 632
Mr = 299.32	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Melting point = 428–429 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.4047 (3) Å	Cell parameters from 3792 reflections
b = 8.7285 (3) Å	θ = 2.1–29.0°
c = 19.5086 (7) Å	µ = 0.10 mm−1
β = 94.113 (2)°	T = 100 K
V = 1427.47 (9) Å3	Block, yellow
Z = 4	0.32 × 0.27 × 0.16 mm

Bruker APEXII CCD diffractometer	3792 independent reflections
Radiation source: sealed tube	2435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.969, Tmax = 0.984	k = −11→11
14970 measured reflections	l = −26→26

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0802P)2 + 1.2643P] where P = (Fo2 + 2Fc2)/3
3792 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.29 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 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	0.6126 (2)	0.93348 (19)	−0.05940 (8)	0.0229 (4)
O2	0.9130 (2)	0.60091 (19)	0.09428 (8)	0.0234 (4)
O3	1.3110 (2)	0.78070 (19)	0.26882 (8)	0.0219 (4)
O4	1.2622 (2)	1.05914 (19)	0.22949 (8)	0.0234 (4)
N1	0.7107 (2)	1.3210 (2)	−0.02122 (10)	0.0194 (4)
C1	0.6314 (3)	1.2048 (3)	−0.05320 (11)	0.0166 (5)
C2	0.5113 (3)	1.2269 (3)	−0.10560 (12)	0.0221 (5)
H2A	0.4597	1.1436	−0.1270	0.027*
C3	0.4706 (3)	1.3755 (3)	−0.12499 (12)	0.0239 (5)
H3A	0.3901	1.3938	−0.1592	0.029*
C4	0.5517 (3)	1.4957 (3)	−0.09262 (12)	0.0234 (5)
H4A	0.5276	1.5964	−0.1050	0.028*
C5	0.6702 (3)	1.4634 (3)	−0.04114 (12)	0.0222 (5)
H5A	0.7241	1.5450	−0.0194	0.027*
C6	0.6774 (3)	1.0442 (3)	−0.03057 (11)	0.0184 (5)
C7	0.7993 (3)	1.0306 (3)	0.02671 (11)	0.0214 (5)
H7A	0.8459	1.1188	0.0459	0.026*
C8	0.8451 (3)	0.8932 (3)	0.05195 (11)	0.0199 (5)
H8A	0.7949	0.8080	0.0315	0.024*
C9	0.9661 (3)	0.8631 (3)	0.10836 (11)	0.0178 (5)
C10	0.9984 (3)	0.7123 (3)	0.12964 (11)	0.0172 (5)
C11	1.1109 (3)	0.6809 (3)	0.18425 (11)	0.0165 (5)
H11A	1.1281	0.5805	0.1989	0.020*
C12	1.1961 (3)	0.7987 (3)	0.21634 (11)	0.0173 (5)
C13	1.1689 (3)	0.9518 (3)	0.19514 (11)	0.0176 (5)
C14	1.0550 (3)	0.9814 (3)	0.14248 (11)	0.0177 (5)
H14A	1.0361	1.0824	0.1290	0.021*
C15	0.9402 (3)	0.4457 (3)	0.11480 (13)	0.0268 (6)
H15A	0.8753	0.3791	0.0853	0.040*
H15B	0.9130	0.4327	0.1614	0.040*
H15C	1.0507	0.4207	0.1115	0.040*
C16	1.3405 (3)	0.6280 (3)	0.29434 (12)	0.0230 (5)
H16A	1.4170	0.6315	0.3333	0.035*
H16B	1.3814	0.5662	0.2589	0.035*
H16C	1.2427	0.5844	0.3079	0.035*
C17	1.2442 (3)	1.2141 (3)	0.20699 (13)	0.0248 (5)
H17A	1.3223	1.2770	0.2319	0.037*
H17B	1.1392	1.2497	0.2153	0.037*
H17C	1.2590	1.2199	0.1587	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0286 (9)	0.0155 (9)	0.0246 (8)	−0.0034 (7)	0.0011 (7)	−0.0018 (7)
O2	0.0307 (10)	0.0092 (8)	0.0283 (8)	−0.0006 (7)	−0.0102 (7)	0.0001 (7)
O3	0.0235 (9)	0.0135 (8)	0.0271 (8)	0.0002 (7)	−0.0089 (7)	0.0034 (7)
O4	0.0269 (9)	0.0110 (9)	0.0307 (9)	−0.0018 (7)	−0.0094 (7)	0.0017 (7)
N1	0.0240 (10)	0.0142 (10)	0.0199 (9)	0.0012 (8)	0.0006 (8)	0.0004 (8)
C1	0.0188 (11)	0.0145 (11)	0.0168 (10)	0.0014 (9)	0.0030 (8)	0.0013 (9)
C2	0.0211 (12)	0.0231 (13)	0.0217 (11)	−0.0010 (10)	−0.0015 (9)	0.0009 (10)
C3	0.0214 (12)	0.0285 (14)	0.0216 (11)	0.0053 (11)	−0.0002 (9)	0.0035 (10)
C4	0.0250 (13)	0.0195 (13)	0.0263 (12)	0.0072 (10)	0.0063 (10)	0.0062 (10)
C5	0.0268 (13)	0.0155 (12)	0.0242 (11)	0.0022 (10)	0.0021 (9)	−0.0002 (9)
C6	0.0224 (12)	0.0167 (12)	0.0163 (10)	−0.0011 (10)	0.0033 (8)	−0.0007 (9)
C7	0.0249 (12)	0.0162 (12)	0.0225 (11)	−0.0009 (10)	−0.0031 (9)	−0.0013 (9)
C8	0.0206 (11)	0.0176 (12)	0.0214 (10)	−0.0014 (10)	−0.0007 (9)	−0.0009 (9)
C9	0.0210 (12)	0.0139 (11)	0.0183 (10)	0.0005 (9)	−0.0003 (9)	0.0011 (9)
C10	0.0189 (11)	0.0125 (11)	0.0202 (10)	−0.0009 (9)	0.0020 (9)	0.0005 (9)
C11	0.0167 (11)	0.0112 (11)	0.0216 (10)	0.0006 (9)	0.0008 (8)	0.0029 (9)
C12	0.0158 (11)	0.0172 (12)	0.0186 (10)	0.0023 (9)	−0.0014 (8)	0.0024 (9)
C13	0.0200 (11)	0.0110 (11)	0.0217 (10)	−0.0016 (9)	0.0009 (9)	0.0002 (9)
C14	0.0229 (12)	0.0108 (11)	0.0196 (10)	0.0013 (9)	0.0030 (9)	0.0018 (9)
C15	0.0369 (14)	0.0125 (12)	0.0295 (12)	−0.0012 (11)	−0.0089 (11)	0.0023 (10)
C16	0.0241 (12)	0.0163 (12)	0.0276 (12)	0.0004 (10)	−0.0049 (10)	0.0060 (10)
C17	0.0277 (13)	0.0115 (11)	0.0342 (13)	−0.0015 (10)	−0.0051 (10)	0.0025 (10)

O1—C6	1.226 (3)	C7—H7A	0.9300
O2—C10	1.366 (3)	C8—C9	1.468 (3)
O2—C15	1.427 (3)	C8—H8A	0.9300
O3—C12	1.365 (3)	C9—C10	1.400 (3)
O3—C16	1.438 (3)	C9—C14	1.413 (3)
O4—C13	1.366 (3)	C10—C11	1.400 (3)
O4—C17	1.427 (3)	C11—C12	1.378 (3)
N1—C5	1.339 (3)	C11—H11A	0.9300
N1—C1	1.343 (3)	C12—C13	1.412 (3)
C1—C2	1.397 (3)	C13—C14	1.377 (3)
C1—C6	1.511 (3)	C14—H14A	0.9300
C2—C3	1.388 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.379 (4)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.392 (3)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.466 (3)	C17—H17B	0.9600
C7—C8	1.343 (3)	C17—H17C	0.9600
C10—O2—C15	117.81 (18)	O2—C10—C9	115.8 (2)
C12—O3—C16	117.48 (18)	C11—C10—C9	121.0 (2)
C13—O4—C17	117.05 (18)	C12—C11—C10	120.0 (2)
C5—N1—C1	117.3 (2)	C12—C11—H11A	120.0
N1—C1—C2	123.0 (2)	C10—C11—H11A	120.0
N1—C1—C6	117.17 (19)	O3—C12—C11	124.8 (2)
C2—C1—C6	119.9 (2)	O3—C12—C13	114.8 (2)
C3—C2—C1	118.6 (2)	C11—C12—C13	120.3 (2)
C3—C2—H2A	120.7	O4—C13—C14	125.5 (2)
C1—C2—H2A	120.7	O4—C13—C12	115.46 (19)
C4—C3—C2	118.9 (2)	C14—C13—C12	119.0 (2)
C4—C3—H3A	120.6	C13—C14—C9	122.0 (2)
C2—C3—H3A	120.6	C13—C14—H14A	119.0
C3—C4—C5	118.7 (2)	C9—C14—H14A	119.0
C3—C4—H4A	120.6	O2—C15—H15A	109.5
C5—C4—H4A	120.6	O2—C15—H15B	109.5
N1—C5—C4	123.5 (2)	H15A—C15—H15B	109.5
N1—C5—H5A	118.3	O2—C15—H15C	109.5
C4—C5—H5A	118.3	H15A—C15—H15C	109.5
O1—C6—C7	123.3 (2)	H15B—C15—H15C	109.5
O1—C6—C1	120.1 (2)	O3—C16—H16A	109.5
C7—C6—C1	116.6 (2)	O3—C16—H16B	109.5
C8—C7—C6	121.2 (2)	H16A—C16—H16B	109.5
C8—C7—H7A	119.4	O3—C16—H16C	109.5
C6—C7—H7A	119.4	H16A—C16—H16C	109.5
C7—C8—C9	126.9 (2)	H16B—C16—H16C	109.5
C7—C8—H8A	116.6	O4—C17—H17A	109.5
C9—C8—H8A	116.6	O4—C17—H17B	109.5
C10—C9—C14	117.6 (2)	H17A—C17—H17B	109.5
C10—C9—C8	120.0 (2)	O4—C17—H17C	109.5
C14—C9—C8	122.5 (2)	H17A—C17—H17C	109.5
O2—C10—C11	123.1 (2)	H17B—C17—H17C	109.5
C5—N1—C1—C2	0.3 (3)	C8—C9—C10—O2	0.9 (3)
C5—N1—C1—C6	−180.0 (2)	C14—C9—C10—C11	2.1 (3)
N1—C1—C2—C3	−0.8 (3)	C8—C9—C10—C11	−178.7 (2)
C6—C1—C2—C3	179.5 (2)	O2—C10—C11—C12	178.1 (2)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	−2.4 (3)
C2—C3—C4—C5	−0.7 (3)	C16—O3—C12—C11	−2.8 (3)
C1—N1—C5—C4	0.0 (3)	C16—O3—C12—C13	177.9 (2)
C3—C4—C5—N1	0.2 (4)	C10—C11—C12—O3	−178.3 (2)
N1—C1—C6—O1	−177.7 (2)	C10—C11—C12—C13	1.0 (3)
C2—C1—C6—O1	2.0 (3)	C17—O4—C13—C14	−2.6 (3)
N1—C1—C6—C7	2.9 (3)	C17—O4—C13—C12	176.7 (2)
C2—C1—C6—C7	−177.4 (2)	O3—C12—C13—O4	0.7 (3)
O1—C6—C7—C8	−1.3 (4)	C11—C12—C13—O4	−178.7 (2)
C1—C6—C7—C8	178.0 (2)	O3—C12—C13—C14	−180.0 (2)
C6—C7—C8—C9	179.4 (2)	C11—C12—C13—C14	0.6 (3)
C7—C8—C9—C10	178.8 (2)	O4—C13—C14—C9	178.4 (2)
C7—C8—C9—C14	−2.0 (4)	C12—C13—C14—C9	−0.9 (3)
C15—O2—C10—C11	0.4 (3)	C10—C9—C14—C13	−0.4 (3)
C15—O2—C10—C9	−179.1 (2)	C8—C9—C14—C13	−179.7 (2)
C14—C9—C10—O2	−178.38 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.93	2.39	3.277 (3)	160
C15—H15A···N1ii	0.96	2.47	3.349 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.93	2.39	3.277 (3)	160
C15—H15A⋯N1ii	0.96	2.47	3.349 (3)	153

Symmetry codes: (i) ; (ii) .