supporting information


Acta Cryst. (2013). E69, o1076-o1077    [ doi:10.1107/S1600536813015821 ]

(2E)-1-(Pyridin-2-yl)-3-(2,4,5-tri­meth­oxy­phen­yl)prop-2-en-1-one

S. Chantrapromma, T. Suwunwong, N. Boonnak and H.-K. Fun

Abstract top

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 meth­oxy 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, mol­ecules are linked by weak C-H...N and C-H...O inter­actions into (100) sheets and an aromatic [pi]-[pi] stacking inter­action between the pyridine and benzene ring, with a centroid-centroid separation of 3.7036 (14) Å also occurs.

Comment top

As part of our ongoing studies of the crystal structures and fluorescent properties of chalcones and heteroaryl chalcones (Chantrapromma et al., 2009; Fun et al., 2010, 2011; Suwunwong et al., 2011, 2012), the title heteroaryl chalcone derivative (I) was synthesized and studied for fluorescent property and for further cyclization purpose. It was also screened for antibacterial and antityrosinase activities and found to be inactive. However it exhibited fluorescence with the emission wavelength at 530 nm when excited at 401 nm. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E conformation with respect to the C7C8 double bond [1.343 (3) Å] and the torsion angle C6–C7–C8–C9 = 179.4 (2)°. The molecule is close to planar with the dihedral angle between pyridine and benzene rings being 3.71 (11)°. Atoms of the middle propenone bridge (C6, C7, C8 and O1) lie almost on the same plane as indicated by the torsion angle O1–C6–C7–C8 = -1.3 (4)°. The mean plane through this bridge makes dihedral angles of 3.03 (15) and 3.06 (15)° with the planes of pyridine and benzene rings, respectively. All the three substituted methoxy groups of 2,4,5-trimethoxyphenyl unit are close to co-planar with the bound benzene ring with the r.m.s. deviation of 0.0290 (2) Å for the twelve non H atoms and the torsion angles C15–O2–C10–C11 = 0.4 (3)°, C16–O3–C12–C13 = 177.9 (2)° and C17–O4–C13–C14 = -2.6 (3)°. The bond distances are comparable with those in related structures (Chantrapromma et al., 2009; Fun et al., 2010; 2011 and Suwunwong et al., 2012).

In the crystal (Fig. 2), only one methoxy group (at atom C10) is involved in weak C—H···N and C—H···O interactions (Table 1). The molecules are linked by weak C15—H15A···N1 and C3—H3A···O4 interactions (Table 1) into (100) sheets. ππ interaction with the Cg1···Cg2iii distance of 3.7036 (14) Å (iii = 2 - x, 2 - y, -z) was presented (Fig. 3); Cg1 and Cg2 are the centroids of N1/C1–C5 and C9–C14 rings, respectively.

Related literature top

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 top

The title compound was synthesized by the condensation of 2,4,5-trimethoxybenzaldehyde (0.40 g, 2 mmol) with 2-acetylpyridine (0.20 g, 2 mmol) in ethanol (30 ml) in the presence of 30% NaOH(aq) (5 ml). After stirring in ice bath at 278 K for 4 h, the resulting yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Yellow blocks of (I) were recrystallized from acetone solution by the slow evaporation of the solvent at room temperature after several days, Mp. 428–429 K.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.93 Å for aromatic and CH, and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of (I) viewed along the a axis, showing molecular sheets parallel to the bc plane. C—H···O and C—H···N interactions are shown as dashed lines.
[Figure 3] Fig. 3. The crystal packing of (I) viewed approximately along the b axis, showing ππ interactions; Cg1 and Cg2 are the centroids of N1/C1–C5 and C9–C14 rings, respectively. H atoms were omitted for clarity.
(2E)-1-(Pyridin-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C17H17NO4F(000) = 632
Mr = 299.32Dx = 1.393 Mg m3
Monoclinic, P21/cMelting point = 428–429 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.4047 (3) ÅCell parameters from 3792 reflections
b = 8.7285 (3) Åθ = 2.1–29.0°
c = 19.5086 (7) ŵ = 0.10 mm1
β = 94.113 (2)°T = 100 K
V = 1427.47 (9) Å3Block, yellow
Z = 40.32 × 0.27 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
3792 independent reflections
Radiation source: sealed tube2435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1011
Tmin = 0.969, Tmax = 0.984k = 1111
14970 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-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 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C17H17NO4V = 1427.47 (9) Å3
Mr = 299.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4047 (3) ŵ = 0.10 mm1
b = 8.7285 (3) ÅT = 100 K
c = 19.5086 (7) Å0.32 × 0.27 × 0.16 mm
β = 94.113 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3792 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2435 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.984Rint = 0.054
14970 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.188H-atom parameters constrained
S = 1.07Δρmax = 0.58 e Å3
3792 reflectionsΔρmin = 0.29 e Å3
202 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6126 (2)0.93348 (19)0.05940 (8)0.0229 (4)
O20.9130 (2)0.60091 (19)0.09428 (8)0.0234 (4)
O31.3110 (2)0.78070 (19)0.26882 (8)0.0219 (4)
O41.2622 (2)1.05914 (19)0.22949 (8)0.0234 (4)
N10.7107 (2)1.3210 (2)0.02122 (10)0.0194 (4)
C10.6314 (3)1.2048 (3)0.05320 (11)0.0166 (5)
C20.5113 (3)1.2269 (3)0.10560 (12)0.0221 (5)
H2A0.45971.14360.12700.027*
C30.4706 (3)1.3755 (3)0.12499 (12)0.0239 (5)
H3A0.39011.39380.15920.029*
C40.5517 (3)1.4957 (3)0.09262 (12)0.0234 (5)
H4A0.52761.59640.10500.028*
C50.6702 (3)1.4634 (3)0.04114 (12)0.0222 (5)
H5A0.72411.54500.01940.027*
C60.6774 (3)1.0442 (3)0.03057 (11)0.0184 (5)
C70.7993 (3)1.0306 (3)0.02671 (11)0.0214 (5)
H7A0.84591.11880.04590.026*
C80.8451 (3)0.8932 (3)0.05195 (11)0.0199 (5)
H8A0.79490.80800.03150.024*
C90.9661 (3)0.8631 (3)0.10836 (11)0.0178 (5)
C100.9984 (3)0.7123 (3)0.12964 (11)0.0172 (5)
C111.1109 (3)0.6809 (3)0.18425 (11)0.0165 (5)
H11A1.12810.58050.19890.020*
C121.1961 (3)0.7987 (3)0.21634 (11)0.0173 (5)
C131.1689 (3)0.9518 (3)0.19514 (11)0.0176 (5)
C141.0550 (3)0.9814 (3)0.14248 (11)0.0177 (5)
H14A1.03611.08240.12900.021*
C150.9402 (3)0.4457 (3)0.11480 (13)0.0268 (6)
H15A0.87530.37910.08530.040*
H15B0.91300.43270.16140.040*
H15C1.05070.42070.11150.040*
C161.3405 (3)0.6280 (3)0.29434 (12)0.0230 (5)
H16A1.41700.63150.33330.035*
H16B1.38140.56620.25890.035*
H16C1.24270.58440.30790.035*
C171.2442 (3)1.2141 (3)0.20699 (13)0.0248 (5)
H17A1.32231.27700.23190.037*
H17B1.13921.24970.21530.037*
H17C1.25901.21990.15870.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0286 (9)0.0155 (9)0.0246 (8)0.0034 (7)0.0011 (7)0.0018 (7)
O20.0307 (10)0.0092 (8)0.0283 (8)0.0006 (7)0.0102 (7)0.0001 (7)
O30.0235 (9)0.0135 (8)0.0271 (8)0.0002 (7)0.0089 (7)0.0034 (7)
O40.0269 (9)0.0110 (9)0.0307 (9)0.0018 (7)0.0094 (7)0.0017 (7)
N10.0240 (10)0.0142 (10)0.0199 (9)0.0012 (8)0.0006 (8)0.0004 (8)
C10.0188 (11)0.0145 (11)0.0168 (10)0.0014 (9)0.0030 (8)0.0013 (9)
C20.0211 (12)0.0231 (13)0.0217 (11)0.0010 (10)0.0015 (9)0.0009 (10)
C30.0214 (12)0.0285 (14)0.0216 (11)0.0053 (11)0.0002 (9)0.0035 (10)
C40.0250 (13)0.0195 (13)0.0263 (12)0.0072 (10)0.0063 (10)0.0062 (10)
C50.0268 (13)0.0155 (12)0.0242 (11)0.0022 (10)0.0021 (9)0.0002 (9)
C60.0224 (12)0.0167 (12)0.0163 (10)0.0011 (10)0.0033 (8)0.0007 (9)
C70.0249 (12)0.0162 (12)0.0225 (11)0.0009 (10)0.0031 (9)0.0013 (9)
C80.0206 (11)0.0176 (12)0.0214 (10)0.0014 (10)0.0007 (9)0.0009 (9)
C90.0210 (12)0.0139 (11)0.0183 (10)0.0005 (9)0.0003 (9)0.0011 (9)
C100.0189 (11)0.0125 (11)0.0202 (10)0.0009 (9)0.0020 (9)0.0005 (9)
C110.0167 (11)0.0112 (11)0.0216 (10)0.0006 (9)0.0008 (8)0.0029 (9)
C120.0158 (11)0.0172 (12)0.0186 (10)0.0023 (9)0.0014 (8)0.0024 (9)
C130.0200 (11)0.0110 (11)0.0217 (10)0.0016 (9)0.0009 (9)0.0002 (9)
C140.0229 (12)0.0108 (11)0.0196 (10)0.0013 (9)0.0030 (9)0.0018 (9)
C150.0369 (14)0.0125 (12)0.0295 (12)0.0012 (11)0.0089 (11)0.0023 (10)
C160.0241 (12)0.0163 (12)0.0276 (12)0.0004 (10)0.0049 (10)0.0060 (10)
C170.0277 (13)0.0115 (11)0.0342 (13)0.0015 (10)0.0051 (10)0.0025 (10)
Geometric parameters (Å, º) top
O1—C61.226 (3)C7—H7A0.9300
O2—C101.366 (3)C8—C91.468 (3)
O2—C151.427 (3)C8—H8A0.9300
O3—C121.365 (3)C9—C101.400 (3)
O3—C161.438 (3)C9—C141.413 (3)
O4—C131.366 (3)C10—C111.400 (3)
O4—C171.427 (3)C11—C121.378 (3)
N1—C51.339 (3)C11—H11A0.9300
N1—C11.343 (3)C12—C131.412 (3)
C1—C21.397 (3)C13—C141.377 (3)
C1—C61.511 (3)C14—H14A0.9300
C2—C31.388 (4)C15—H15A0.9600
C2—H2A0.9300C15—H15B0.9600
C3—C41.379 (4)C15—H15C0.9600
C3—H3A0.9300C16—H16A0.9600
C4—C51.392 (3)C16—H16B0.9600
C4—H4A0.9300C16—H16C0.9600
C5—H5A0.9300C17—H17A0.9600
C6—C71.466 (3)C17—H17B0.9600
C7—C81.343 (3)C17—H17C0.9600
C10—O2—C15117.81 (18)O2—C10—C9115.8 (2)
C12—O3—C16117.48 (18)C11—C10—C9121.0 (2)
C13—O4—C17117.05 (18)C12—C11—C10120.0 (2)
C5—N1—C1117.3 (2)C12—C11—H11A120.0
N1—C1—C2123.0 (2)C10—C11—H11A120.0
N1—C1—C6117.17 (19)O3—C12—C11124.8 (2)
C2—C1—C6119.9 (2)O3—C12—C13114.8 (2)
C3—C2—C1118.6 (2)C11—C12—C13120.3 (2)
C3—C2—H2A120.7O4—C13—C14125.5 (2)
C1—C2—H2A120.7O4—C13—C12115.46 (19)
C4—C3—C2118.9 (2)C14—C13—C12119.0 (2)
C4—C3—H3A120.6C13—C14—C9122.0 (2)
C2—C3—H3A120.6C13—C14—H14A119.0
C3—C4—C5118.7 (2)C9—C14—H14A119.0
C3—C4—H4A120.6O2—C15—H15A109.5
C5—C4—H4A120.6O2—C15—H15B109.5
N1—C5—C4123.5 (2)H15A—C15—H15B109.5
N1—C5—H5A118.3O2—C15—H15C109.5
C4—C5—H5A118.3H15A—C15—H15C109.5
O1—C6—C7123.3 (2)H15B—C15—H15C109.5
O1—C6—C1120.1 (2)O3—C16—H16A109.5
C7—C6—C1116.6 (2)O3—C16—H16B109.5
C8—C7—C6121.2 (2)H16A—C16—H16B109.5
C8—C7—H7A119.4O3—C16—H16C109.5
C6—C7—H7A119.4H16A—C16—H16C109.5
C7—C8—C9126.9 (2)H16B—C16—H16C109.5
C7—C8—H8A116.6O4—C17—H17A109.5
C9—C8—H8A116.6O4—C17—H17B109.5
C10—C9—C14117.6 (2)H17A—C17—H17B109.5
C10—C9—C8120.0 (2)O4—C17—H17C109.5
C14—C9—C8122.5 (2)H17A—C17—H17C109.5
O2—C10—C11123.1 (2)H17B—C17—H17C109.5
C5—N1—C1—C20.3 (3)C8—C9—C10—O20.9 (3)
C5—N1—C1—C6180.0 (2)C14—C9—C10—C112.1 (3)
N1—C1—C2—C30.8 (3)C8—C9—C10—C11178.7 (2)
C6—C1—C2—C3179.5 (2)O2—C10—C11—C12178.1 (2)
C1—C2—C3—C41.0 (3)C9—C10—C11—C122.4 (3)
C2—C3—C4—C50.7 (3)C16—O3—C12—C112.8 (3)
C1—N1—C5—C40.0 (3)C16—O3—C12—C13177.9 (2)
C3—C4—C5—N10.2 (4)C10—C11—C12—O3178.3 (2)
N1—C1—C6—O1177.7 (2)C10—C11—C12—C131.0 (3)
C2—C1—C6—O12.0 (3)C17—O4—C13—C142.6 (3)
N1—C1—C6—C72.9 (3)C17—O4—C13—C12176.7 (2)
C2—C1—C6—C7177.4 (2)O3—C12—C13—O40.7 (3)
O1—C6—C7—C81.3 (4)C11—C12—C13—O4178.7 (2)
C1—C6—C7—C8178.0 (2)O3—C12—C13—C14180.0 (2)
C6—C7—C8—C9179.4 (2)C11—C12—C13—C140.6 (3)
C7—C8—C9—C10178.8 (2)O4—C13—C14—C9178.4 (2)
C7—C8—C9—C142.0 (4)C12—C13—C14—C90.9 (3)
C15—O2—C10—C110.4 (3)C10—C9—C14—C130.4 (3)
C15—O2—C10—C9179.1 (2)C8—C9—C14—C13179.7 (2)
C14—C9—C10—O2178.38 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O4i0.932.393.277 (3)160
C15—H15A···N1ii0.962.473.349 (3)153
Symmetry codes: (i) x1, y+5/2, z1/2; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H17NO4
Mr299.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.4047 (3), 8.7285 (3), 19.5086 (7)
β (°) 94.113 (2)
V3)1427.47 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.32 × 0.27 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.969, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
14970, 3792, 2435
Rint0.054
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.188, 1.07
No. of reflections3792
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O4i0.932.393.277 (3)160
C15—H15A···N1ii0.962.473.349 (3)153
Symmetry codes: (i) x1, y+5/2, z1/2; (ii) x, y1, z.
 
Acknowledgements top

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) is gratefully acknowledged. The authors extend their appreciation to Prince of Songkla University, the Deanship of Scientific Research at the King Saud University and Universiti Sains Malaysia for the APEX DE2012 grant No.1002/PFIZIK/910323.