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Acta Cryst. (2009). E65, o1065    [ doi:10.1107/S1600536809013944 ]

3-(3,4-Dimethoxyphenyl)-1-(3-pyridyl)prop-2-en-1-one monohydrate

A. Jayarama and S. W. Ng

Abstract top

The pyridyl and aryl rings in the title compound, C16H15NO3·H2O, which are located at the ends of the propenone unit, are nearly coplanar with this unit [dihedral angles = 3.74 (14) and 5.06 (13)°, respectively]; the rings are inclined at an angle of 6.2 (1)° with respect to each other. The solvent water molecule forms hydrogen bonds with the pyridyl N atom and also with a symmetry-related water molecule.

Comment top

Some chalcone derivatives exhibit high second-harmonic generation conversion efficiency (Gu et al., 2008; Ravindra et al., 2008a,b). The title compound was synthesized for the purpose of examining this property; unfortunately, the compound crystallizes in a centrosymmetric space group.

Related literature top

For 3-(4-chlorophenyl)-1-(3-pyridyl)prop-2-en-1-one, which belongs to a non-centrosymmetric space group, see: Uchida et al. (1998). For the general synthesis by the Claisen–Schmidt condensation, see: Vogel (1999). For literature on related compounds exhibiting second-harmonic generation activity, see: Gu et al. (2008); Ravindra et al. (2008a,b).

Experimental top

The compound was synthesized by the Claisen–Schmidt condensation (Vogel, 1999). To a mixture of ethanol (20 ml) and 10% sodium hydroxide solution (5 ml) was added an ethanol (15 ml) solution of 3-acetyl pyridine (0.001 mol) and 3,4-dimethoxybenzaldehyde (0.001 mol). The temperature of the mixture was maintained at below 298 K for 2 h. The solid product that formed was washed with water. The compound was recrystallized from methanol.

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) constrained to 1.2–1.5Ueq(C). The water H atoms were located in a difference Fourier map, and were refined with a distance restraint of O—H = 0.84 (1) Å; their isotropic temperature factors were refined.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.
3-(3,4-Dimethoxyphenyl)-1-(3-pyridyl)prop-2-en-1-one monohydrate top
Crystal data top
C16H15NO3·H2OF(000) = 608
Mr = 287.31Dx = 1.322 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2693 reflections
a = 17.9809 (4) Åθ = 2.3–28.2°
b = 4.5004 (1) ŵ = 0.10 mm−1
c = 18.2230 (4) ÅT = 100 K
β = 101.775 (2)°Prism, yellow
V = 1443.60 (6) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
graphiteθmax = 27.5°, θmin = 1.5°
ω scansh = −23→23
12630 measured reflectionsk = −5→5
3315 independent reflectionsl = −23→23
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.3539P]
where P = (Fo2 + 2Fc2)/3
3315 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.52 e Å−3
2 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C16H15NO3·H2OV = 1443.60 (6) Å3
Mr = 287.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.9809 (4) ŵ = 0.10 mm−1
b = 4.5004 (1) ÅT = 100 K
c = 18.2230 (4) Å0.20 × 0.15 × 0.10 mm
β = 101.775 (2)°
Data collection top
Bruker SMART APEX
diffractometer		2362 reflections with I > 2σ(I)
12630 measured reflectionsRint = 0.041
3315 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 0.52 e Å−3
S = 1.02Δρmin = −0.20 e Å−3
3315 reflectionsAbsolute structure: ?
200 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41877 (6)0.8369 (3)0.27622 (7)0.0397 (3)
O20.80564 (6)0.3782 (3)0.50243 (6)0.0340 (3)
O30.76194 (6)0.0474 (3)0.59966 (6)0.0332 (3)
O1W0.74070 (7)1.5349 (3)0.20508 (8)0.0402 (3)
H110.6951 (6)1.524 (5)0.1836 (11)0.059 (7)*
H120.748 (4)1.409 (13)0.241 (3)0.27 (3)*
N10.58178 (7)1.4202 (3)0.15840 (8)0.0308 (3)
C10.52118 (9)1.5143 (4)0.10854 (9)0.0316 (4)
H10.52901.65200.07130.038*
C20.44804 (9)1.4221 (4)0.10827 (10)0.0351 (4)
H20.40661.49380.07160.042*
C30.43629 (8)1.2243 (4)0.16218 (9)0.0313 (4)
H30.38641.15820.16330.038*
C40.49781 (8)1.1211 (3)0.21511 (8)0.0251 (3)
C50.56925 (8)1.2269 (4)0.21027 (9)0.0279 (4)
H50.61181.15770.24600.034*
C60.48429 (8)0.9066 (4)0.27391 (9)0.0271 (4)
C70.54975 (8)0.7857 (4)0.32741 (9)0.0274 (4)
H70.59960.85150.32570.033*
C80.53984 (8)0.5844 (4)0.37843 (9)0.0265 (3)
H80.48890.52640.37770.032*
C90.59780 (8)0.4441 (3)0.43488 (8)0.0244 (3)
C100.67609 (8)0.4868 (4)0.43855 (9)0.0260 (3)
H100.69270.60990.40270.031*
C110.72834 (8)0.3517 (4)0.49363 (9)0.0262 (3)
C120.70494 (8)0.1676 (3)0.54753 (9)0.0267 (4)
C130.62805 (9)0.1256 (4)0.54443 (9)0.0279 (4)
H130.61140.00450.58060.034*
C140.57558 (8)0.2614 (4)0.48808 (9)0.0267 (3)
H140.52300.22880.48580.032*
C150.83247 (9)0.5723 (4)0.45185 (10)0.0317 (4)
H15A0.88810.57950.46440.048*
H15B0.81200.77210.45580.048*
H15C0.81580.49880.40050.048*
C160.74125 (10)−0.1299 (4)0.65737 (10)0.0365 (4)
H16A0.7872−0.19160.69290.055*
H16B0.7136−0.30630.63500.055*
H16C0.7088−0.01360.68380.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0184 (6)0.0609 (9)0.0394 (7)−0.0013 (5)0.0049 (5)0.0074 (6)
O20.0173 (5)0.0427 (7)0.0417 (7)0.0009 (5)0.0052 (5)0.0096 (6)
O30.0228 (5)0.0391 (7)0.0363 (7)0.0030 (5)0.0029 (5)0.0096 (5)
O1W0.0225 (6)0.0420 (7)0.0526 (8)−0.0010 (5)−0.0007 (6)0.0041 (7)
N10.0228 (6)0.0373 (8)0.0318 (7)−0.0007 (6)0.0042 (5)−0.0019 (6)
C10.0300 (8)0.0321 (9)0.0312 (9)−0.0011 (7)0.0031 (7)0.0003 (7)
C20.0250 (8)0.0379 (10)0.0383 (10)0.0003 (7)−0.0034 (7)0.0035 (8)
C30.0200 (7)0.0346 (9)0.0368 (9)−0.0010 (7)0.0005 (7)−0.0015 (8)
C40.0205 (7)0.0283 (8)0.0256 (8)0.0018 (6)0.0030 (6)−0.0062 (6)
C50.0202 (7)0.0346 (9)0.0280 (8)0.0030 (6)0.0027 (6)−0.0035 (7)
C60.0215 (7)0.0328 (9)0.0267 (8)0.0023 (6)0.0038 (6)−0.0050 (7)
C70.0198 (7)0.0317 (9)0.0295 (8)0.0003 (6)0.0027 (6)−0.0043 (7)
C80.0195 (7)0.0307 (8)0.0289 (8)0.0004 (6)0.0036 (6)−0.0069 (7)
C90.0215 (7)0.0244 (8)0.0268 (8)−0.0004 (6)0.0036 (6)−0.0063 (6)
C100.0218 (7)0.0276 (8)0.0290 (8)−0.0001 (6)0.0063 (6)−0.0018 (7)
C110.0181 (7)0.0289 (8)0.0320 (8)−0.0002 (6)0.0060 (6)−0.0028 (7)
C120.0230 (7)0.0264 (8)0.0298 (8)0.0026 (6)0.0030 (6)−0.0027 (7)
C130.0264 (8)0.0271 (8)0.0308 (8)−0.0021 (6)0.0069 (6)−0.0013 (7)
C140.0194 (7)0.0279 (8)0.0328 (8)−0.0021 (6)0.0056 (6)−0.0038 (7)
C150.0213 (7)0.0362 (9)0.0386 (9)−0.0026 (7)0.0085 (7)0.0014 (8)
C160.0334 (9)0.0400 (10)0.0357 (9)0.0040 (8)0.0059 (7)0.0078 (8)
Geometric parameters (Å, °) top
O1—C61.2282 (18)C7—C81.336 (2)
O2—C111.3714 (17)C7—H70.9500
O2—C151.4237 (19)C8—C91.451 (2)
O3—C121.3596 (18)C8—H80.9500
O3—C161.429 (2)C9—C141.390 (2)
O1W—H110.84 (1)C9—C101.409 (2)
O1W—H120.85 (1)C10—C111.369 (2)
N1—C11.337 (2)C10—H100.9500
N1—C51.337 (2)C11—C121.413 (2)
C1—C21.378 (2)C12—C131.385 (2)
C1—H10.9500C13—C141.387 (2)
C2—C31.374 (2)C13—H130.9500
C2—H20.9500C14—H140.9500
C3—C41.391 (2)C15—H15A0.9800
C3—H30.9500C15—H15B0.9800
C4—C51.390 (2)C15—H15C0.9800
C4—C61.499 (2)C16—H16A0.9800
C5—H50.9500C16—H16B0.9800
C6—C71.471 (2)C16—H16C0.9800
C11—O2—C15116.54 (12)C14—C9—C8118.98 (13)
C12—O3—C16117.66 (12)C10—C9—C8122.71 (14)
H11—O1W—H12108 (5)C11—C10—C9120.24 (15)
C1—N1—C5117.06 (13)C11—C10—H10119.9
N1—C1—C2123.50 (16)C9—C10—H10119.9
N1—C1—H1118.3C10—C11—O2125.07 (14)
C2—C1—H1118.3C10—C11—C12120.85 (14)
C3—C2—C1118.58 (15)O2—C11—C12114.08 (13)
C3—C2—H2120.7O3—C12—C13125.32 (14)
C1—C2—H2120.7O3—C12—C11115.47 (13)
C2—C3—C4119.73 (15)C13—C12—C11119.21 (14)
C2—C3—H3120.1C12—C13—C14119.52 (15)
C4—C3—H3120.1C12—C13—H13120.2
C5—C4—C3117.15 (15)C14—C13—H13120.2
C5—C4—C6123.58 (14)C13—C14—C9121.87 (14)
C3—C4—C6119.27 (14)C13—C14—H14119.1
N1—C5—C4123.99 (14)C9—C14—H14119.1
N1—C5—H5118.0O2—C15—H15A109.5
C4—C5—H5118.0O2—C15—H15B109.5
O1—C6—C7121.76 (15)H15A—C15—H15B109.5
O1—C6—C4119.06 (14)O2—C15—H15C109.5
C7—C6—C4119.17 (13)H15A—C15—H15C109.5
C8—C7—C6120.64 (14)H15B—C15—H15C109.5
C8—C7—H7119.7O3—C16—H16A109.5
C6—C7—H7119.7O3—C16—H16B109.5
C7—C8—C9127.59 (14)H16A—C16—H16B109.5
C7—C8—H8116.2O3—C16—H16C109.5
C9—C8—H8116.2H16A—C16—H16C109.5
C14—C9—C10118.31 (14)H16B—C16—H16C109.5
C5—N1—C1—C2−0.1 (2)C14—C9—C10—C11−0.3 (2)
N1—C1—C2—C30.4 (3)C8—C9—C10—C11179.17 (14)
C1—C2—C3—C4−0.3 (3)C9—C10—C11—O2−179.94 (14)
C2—C3—C4—C50.1 (2)C9—C10—C11—C120.1 (2)
C2—C3—C4—C6179.67 (15)C15—O2—C11—C102.9 (2)
C1—N1—C5—C4−0.2 (2)C15—O2—C11—C12−177.12 (14)
C3—C4—C5—N10.2 (2)C16—O3—C12—C13−1.9 (2)
C6—C4—C5—N1−179.40 (15)C16—O3—C12—C11177.32 (14)
C5—C4—C6—O1176.30 (15)C10—C11—C12—O3−179.61 (14)
C3—C4—C6—O1−3.3 (2)O2—C11—C12—O30.4 (2)
C5—C4—C6—C7−3.6 (2)C10—C11—C12—C13−0.3 (2)
C3—C4—C6—C7176.84 (14)O2—C11—C12—C13179.69 (14)
O1—C6—C7—C83.0 (2)O3—C12—C13—C14−179.96 (14)
C4—C6—C7—C8−177.10 (14)C11—C12—C13—C140.8 (2)
C6—C7—C8—C9−179.94 (14)C12—C13—C14—C9−1.1 (2)
C7—C8—C9—C14173.53 (15)C10—C9—C14—C130.8 (2)
C7—C8—C9—C10−5.9 (3)C8—C9—C14—C13−178.66 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11···N10.83 (1)2.05 (1)2.857 (2)163 (2)
O1W—H12···O1Wi0.85 (1)1.94 (3)2.763 (2)162 (7)
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11···N10.83 (1)2.05 (1)2.857 (2)163 (2)
O1W—H12···O1Wi0.85 (1)1.94 (3)2.763 (2)162 (7)
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2.
Acknowledgements top

The authors thank the Mangalore Institute of Technology and Engineering and the University of Malaya for supporting this study.

references
References top

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