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

In the title heteroaryl chalcone derivative, C(17)H(17)NO(4), the dihedral angle between the pyridine and benzene rings is 10.82 (5)°. The two meth-oxy groups at the meta positions are essentially coplanar with the attached benzene rings [C-O-C-C torsion angles = -0.97 (14) and 179.47 (9)°], whereas the meth-oxy group at the para position is twisted from the attached ring with a C-O-C-C torsion angle of -104.48 (11)°. A C-H⋯O close contact involving two of the meth-oxy groups generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into columns along the b axis.

Related literature

For background and applications of chalcones, see: Gacche et al. (2008 ▶); Isomoto et al. (2005 ▶); Jung et al. (2008 ▶); Nowakowska et al. (2001 ▶); Patil & Dharmaprakash (2008 ▶); Shibata (1994 ▶); Tewtrakul et al. (2003 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶); Suwunwong, Chantrapromma & Fun (2009 ▶); Suwunwong, Chantrapromma, Pakdeevanich & Fun (2009 ▶). 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 = 25.0498 (5) Å

b = 3.9799 (1) Å

c = 14.3267 (3) Å

V = 1428.31 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.58 × 0.41 × 0.32 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.969

26700 measured reflections

3245 independent reflections

3130 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.08

3245 reflections

202 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.21 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/S1600536811033198/lh5312sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033198/lh5312Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033198/lh5312Isup3.cml

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

C17H17NO4	Dx = 1.392 Mg m−3
Mr = 299.32	Melting point = 434–435 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3245 reflections
a = 25.0498 (5) Å	θ = 2.2–35.0°
b = 3.9799 (1) Å	µ = 0.10 mm−1
c = 14.3267 (3) Å	T = 100 K
V = 1428.31 (5) Å3	Block, pale yellow
Z = 4	0.58 × 0.41 × 0.32 mm
F(000) = 632

Bruker APEXII CCD area-detector diffractometer	3245 independent reflections
Radiation source: sealed tube	3130 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 35.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −34→40
Tmin = 0.945, Tmax = 0.969	k = −6→6
26700 measured reflections	l = −23→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.087P] where P = (Fo2 + 2Fc2)/3
3245 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.21 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	0.24601 (4)	−0.1060 (3)	0.05761 (7)	0.02596 (19)
O2	0.08957 (3)	0.0024 (2)	0.50009 (5)	0.01754 (15)
O3	0.00155 (3)	0.3315 (2)	0.44825 (6)	0.01804 (15)
O4	−0.01556 (3)	0.5094 (2)	0.26892 (6)	0.01841 (15)
C4	0.23610 (4)	−0.0027 (3)	−0.13617 (8)	0.01727 (17)
H4A	0.2657	−0.1252	−0.1167	0.021*
C3	0.22725 (5)	0.0591 (3)	−0.23046 (8)	0.01872 (18)
H3A	0.2504	−0.0255	−0.2754	0.022*
C2	0.18322 (5)	0.2495 (3)	−0.25613 (7)	0.01913 (18)
H2A	0.1766	0.2978	−0.3186	0.023*
C1	0.14921 (4)	0.3668 (3)	−0.18655 (8)	0.01865 (19)
H1A	0.1198	0.4947	−0.2042	0.022*
N1	0.15656 (4)	0.3053 (2)	−0.09560 (6)	0.01632 (16)
C5	0.19958 (4)	0.1232 (2)	−0.07164 (7)	0.01393 (16)
C6	0.20623 (4)	0.0461 (3)	0.03063 (7)	0.01630 (17)
C7	0.16244 (4)	0.1520 (3)	0.09225 (7)	0.01565 (17)
H7A	0.1354	0.2880	0.0687	0.019*
C8	0.16076 (4)	0.0553 (3)	0.18220 (7)	0.01548 (16)
H8A	0.1893	−0.0724	0.2037	0.019*
C9	0.11859 (4)	0.1310 (3)	0.24945 (7)	0.01371 (16)
C10	0.12577 (4)	0.0284 (3)	0.34211 (7)	0.01412 (16)
H10A	0.1570	−0.0816	0.3596	0.017*
C11	0.08615 (4)	0.0913 (2)	0.40822 (6)	0.01337 (16)
C12	0.03898 (4)	0.2565 (3)	0.38196 (7)	0.01385 (15)
C13	0.03186 (4)	0.3557 (2)	0.28851 (7)	0.01376 (16)
C14	0.07153 (4)	0.2953 (3)	0.22275 (7)	0.01422 (16)
H14A	0.0669	0.3638	0.1612	0.017*
C15	0.13684 (5)	−0.1702 (3)	0.52820 (8)	0.01924 (18)
H15A	0.1339	−0.2324	0.5927	0.029*
H15B	0.1672	−0.0258	0.5199	0.029*
H15C	0.1412	−0.3686	0.4909	0.029*
C16	−0.04469 (5)	0.1175 (3)	0.44731 (9)	0.02059 (19)
H16A	−0.0727	0.2196	0.4831	0.031*
H16B	−0.0357	−0.0964	0.4740	0.031*
H16C	−0.0565	0.0864	0.3841	0.031*
C17	−0.02386 (5)	0.6161 (3)	0.17457 (8)	0.01905 (19)
H17A	−0.0580	0.7245	0.1695	0.029*
H17B	−0.0229	0.4244	0.1339	0.029*
H17C	0.0038	0.7709	0.1570	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0183 (4)	0.0404 (5)	0.0192 (4)	0.0113 (3)	0.0019 (3)	0.0060 (4)
O2	0.0191 (4)	0.0228 (4)	0.0107 (3)	0.0004 (3)	−0.0005 (2)	0.0022 (2)
O3	0.0168 (3)	0.0225 (3)	0.0148 (3)	−0.0011 (3)	0.0040 (3)	−0.0044 (3)
O4	0.0152 (3)	0.0256 (4)	0.0144 (3)	0.0049 (3)	0.0000 (3)	0.0018 (3)
C4	0.0158 (4)	0.0190 (4)	0.0171 (4)	0.0019 (3)	0.0036 (3)	0.0001 (3)
C3	0.0215 (5)	0.0190 (4)	0.0157 (4)	−0.0015 (3)	0.0065 (4)	−0.0015 (3)
C2	0.0220 (5)	0.0218 (4)	0.0136 (4)	−0.0027 (4)	0.0009 (3)	0.0001 (3)
C1	0.0178 (4)	0.0238 (5)	0.0144 (4)	0.0007 (3)	−0.0011 (3)	0.0019 (3)
N1	0.0134 (3)	0.0218 (4)	0.0137 (3)	0.0011 (3)	0.0000 (3)	0.0012 (3)
C5	0.0126 (4)	0.0168 (4)	0.0124 (3)	−0.0001 (3)	0.0017 (3)	0.0006 (3)
C6	0.0136 (4)	0.0210 (4)	0.0143 (4)	0.0013 (3)	0.0012 (3)	0.0012 (3)
C7	0.0140 (4)	0.0203 (4)	0.0126 (3)	0.0018 (3)	0.0013 (3)	0.0003 (3)
C8	0.0146 (4)	0.0188 (4)	0.0131 (4)	0.0012 (3)	0.0006 (3)	0.0003 (3)
C9	0.0132 (4)	0.0162 (4)	0.0117 (3)	−0.0009 (3)	0.0002 (3)	0.0000 (3)
C10	0.0133 (4)	0.0178 (4)	0.0112 (3)	0.0003 (3)	−0.0006 (3)	0.0003 (3)
C11	0.0149 (4)	0.0149 (4)	0.0103 (3)	−0.0014 (3)	−0.0004 (3)	−0.0001 (3)
C12	0.0144 (4)	0.0157 (4)	0.0114 (3)	−0.0005 (3)	0.0003 (3)	−0.0014 (3)
C13	0.0129 (4)	0.0157 (4)	0.0127 (3)	0.0003 (3)	−0.0005 (3)	−0.0011 (3)
C14	0.0130 (4)	0.0179 (4)	0.0118 (3)	−0.0001 (3)	−0.0001 (3)	0.0003 (3)
C15	0.0227 (5)	0.0193 (4)	0.0157 (4)	−0.0006 (3)	−0.0038 (4)	0.0031 (3)
C16	0.0180 (4)	0.0202 (4)	0.0235 (5)	−0.0009 (3)	0.0060 (4)	0.0008 (4)
C17	0.0177 (4)	0.0226 (5)	0.0168 (4)	0.0018 (3)	−0.0027 (3)	0.0038 (3)

O1—C6	1.2285 (13)	C7—H7A	0.9300
O2—C11	1.3656 (12)	C8—C9	1.4611 (14)
O2—C15	1.4269 (14)	C8—H8A	0.9300
O3—C12	1.3676 (12)	C9—C10	1.4005 (14)
O3—C16	1.4376 (14)	C9—C14	1.4013 (14)
O4—C13	1.3654 (13)	C10—C11	1.3946 (14)
O4—C17	1.4320 (14)	C10—H10A	0.9300
C4—C3	1.3909 (16)	C11—C12	1.4034 (14)
C4—C5	1.3938 (14)	C12—C13	1.4072 (13)
C4—H4A	0.9300	C13—C14	1.3904 (14)
C3—C2	1.3877 (17)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9600
C2—C1	1.3918 (16)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C1—N1	1.3386 (14)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
N1—C5	1.3434 (13)	C16—H16C	0.9600
C5—C6	1.5061 (14)	C17—H17A	0.9600
C6—C7	1.4697 (14)	C17—H17B	0.9600
C7—C8	1.3456 (14)	C17—H17C	0.9600
C11—O2—C15	116.68 (9)	C11—C10—H10A	120.0
C12—O3—C16	114.63 (8)	C9—C10—H10A	120.0
C13—O4—C17	116.95 (8)	O2—C11—C10	124.28 (9)
C3—C4—C5	118.42 (10)	O2—C11—C12	115.64 (9)
C3—C4—H4A	120.8	C10—C11—C12	120.08 (9)
C5—C4—H4A	120.8	O3—C12—C11	119.55 (9)
C2—C3—C4	118.73 (9)	O3—C12—C13	120.83 (9)
C2—C3—H3A	120.6	C11—C12—C13	119.56 (9)
C4—C3—H3A	120.6	O4—C13—C14	124.05 (9)
C3—C2—C1	118.68 (10)	O4—C13—C12	115.58 (8)
C3—C2—H2A	120.7	C14—C13—C12	120.37 (9)
C1—C2—H2A	120.7	C13—C14—C9	119.80 (9)
N1—C1—C2	123.48 (10)	C13—C14—H14A	120.1
N1—C1—H1A	118.3	C9—C14—H14A	120.1
C2—C1—H1A	118.3	O2—C15—H15A	109.5
C1—N1—C5	117.24 (9)	O2—C15—H15B	109.5
N1—C5—C4	123.44 (9)	H15A—C15—H15B	109.5
N1—C5—C6	116.56 (8)	O2—C15—H15C	109.5
C4—C5—C6	119.96 (9)	H15A—C15—H15C	109.5
O1—C6—C7	123.89 (10)	H15B—C15—H15C	109.5
O1—C6—C5	119.75 (10)	O3—C16—H16A	109.5
C7—C6—C5	116.32 (9)	O3—C16—H16B	109.5
C8—C7—C6	121.12 (9)	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	126.53 (9)	H16B—C16—H16C	109.5
C7—C8—H8A	116.7	O4—C17—H17A	109.5
C9—C8—H8A	116.7	O4—C17—H17B	109.5
C10—C9—C14	120.19 (9)	H17A—C17—H17B	109.5
C10—C9—C8	118.17 (9)	O4—C17—H17C	109.5
C14—C9—C8	121.63 (9)	H17A—C17—H17C	109.5
C11—C10—C9	120.00 (9)	H17B—C17—H17C	109.5
C5—C4—C3—C2	1.43 (16)	C15—O2—C11—C12	179.12 (9)
C4—C3—C2—C1	−0.96 (17)	C9—C10—C11—O2	−179.72 (9)
C3—C2—C1—N1	−0.13 (18)	C9—C10—C11—C12	0.18 (15)
C2—C1—N1—C5	0.71 (17)	C16—O3—C12—C11	−104.48 (11)
C1—N1—C5—C4	−0.19 (15)	C16—O3—C12—C13	78.28 (12)
C1—N1—C5—C6	−177.94 (10)	O2—C11—C12—O3	3.10 (14)
C3—C4—C5—N1	−0.88 (16)	C10—C11—C12—O3	−176.82 (9)
C3—C4—C5—C6	176.80 (10)	O2—C11—C12—C13	−179.63 (8)
N1—C5—C6—O1	−176.67 (11)	C10—C11—C12—C13	0.45 (14)
C4—C5—C6—O1	5.50 (16)	C17—O4—C13—C14	−0.67 (15)
N1—C5—C6—C7	5.36 (14)	C17—O4—C13—C12	179.47 (9)
C4—C5—C6—C7	−172.47 (10)	O3—C12—C13—O4	−3.86 (14)
O1—C6—C7—C8	−7.16 (18)	C11—C12—C13—O4	178.91 (9)
C5—C6—C7—C8	170.72 (10)	O3—C12—C13—C14	176.28 (9)
C6—C7—C8—C9	−177.30 (10)	C11—C12—C13—C14	−0.96 (14)
C7—C8—C9—C10	−175.49 (10)	O4—C13—C14—C9	−179.04 (9)
C7—C8—C9—C14	5.80 (17)	C12—C13—C14—C9	0.81 (14)
C14—C9—C10—C11	−0.33 (15)	C10—C9—C14—C13	−0.16 (15)
C8—C9—C10—C11	−179.06 (9)	C8—C9—C14—C13	178.52 (9)
C15—O2—C11—C10	−0.97 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O3i	0.96	2.49	3.3358 (14)	147
C16—H16C···O4	0.96	2.57	3.0817 (15)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O3i	0.96	2.49	3.3358 (14)	147
C16—H16C⋯O4	0.96	2.57	3.0817 (15)	113

Symmetry code: (i) .