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Acta Cryst. (2009). E65, o1066    [ doi:10.1107/S1600536809013956 ]

3-[4-(Dimethylamino)phenyl]-1-(3-pyridyl)prop-2-en-1-one

A. Jayarama and S. W. Ng

Abstract top

The pyridyl and aryl rings in the title compound, C16H16N2O, which are located at the ends of the propenone unit, are inclined at an angle of 17.1 (1)° with respect to each other.

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-(pyrid-3-yl)prop-2-en-1-one, which crystallizes in 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 4-dimethylaminobenzaldehyde (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

H atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) restrained to 1.2–1.5Ueq(C).

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 C16H16N2O at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.
3-[4-(Dimethylamino)phenyl]-1-(3-pyridyl)prop-2-en-1-one top
Crystal data top
C16H16N2OF(000) = 1072
Mr = 252.31Dx = 1.293 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1330 reflections
a = 14.6672 (6) Åθ = 2.5–24.9°
b = 11.0644 (4) ŵ = 0.08 mm−1
c = 16.7272 (6) ÅT = 100 K
β = 107.205 (3)°Plate, orange
V = 2593.1 (2) Å30.20 × 0.20 × 0.03 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		1817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
graphiteθmax = 27.5°, θmin = 2.4°
ω scansh = −19→18
11747 measured reflectionsk = −14→14
2976 independent reflectionsl = −21→21
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.8849P]
where P = (Fo2 + 2Fc2)/3
2976 reflections(Δ/σ)max = 0.001
174 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C16H16N2OV = 2593.1 (2) Å3
Mr = 252.31Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.6672 (6) ŵ = 0.08 mm−1
b = 11.0644 (4) ÅT = 100 K
c = 16.7272 (6) Å0.20 × 0.20 × 0.03 mm
β = 107.205 (3)°
Data collection top
Bruker SMART APEX
diffractometer		1817 reflections with I > 2σ(I)
11747 measured reflectionsRint = 0.063
2976 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.22 e Å−3
S = 1.02Δρmin = −0.28 e Å−3
2976 reflectionsAbsolute structure: ?
174 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.70214 (10)0.23165 (12)0.74962 (8)0.0328 (4)
N10.60015 (14)0.57819 (16)0.86721 (11)0.0408 (5)
N20.89331 (12)0.58854 (14)0.38128 (10)0.0270 (4)
C10.55057 (16)0.5062 (2)0.90340 (14)0.0394 (6)
H10.51850.54230.93900.047*
C20.54329 (15)0.3828 (2)0.89203 (13)0.0314 (5)
H20.50730.33540.91920.038*
C30.58905 (14)0.33046 (18)0.84076 (12)0.0273 (5)
H30.58550.24550.83220.033*
C40.64088 (13)0.40126 (16)0.80103 (11)0.0242 (4)
C50.64452 (15)0.52517 (17)0.81678 (12)0.0292 (5)
H50.68020.57460.79050.035*
C60.69040 (13)0.34254 (16)0.74515 (12)0.0240 (4)
C70.72162 (14)0.41654 (17)0.68607 (12)0.0268 (5)
H70.71080.50130.68460.032*
C80.76531 (13)0.36800 (17)0.63362 (11)0.0250 (4)
H80.77500.28310.63800.030*
C90.79945 (13)0.42798 (16)0.57141 (11)0.0226 (4)
C100.83957 (14)0.35986 (17)0.51975 (12)0.0259 (5)
H100.84510.27480.52770.031*
C110.87122 (14)0.41098 (16)0.45818 (12)0.0254 (4)
H110.89730.36100.42430.030*
C120.86545 (13)0.53701 (16)0.44457 (11)0.0225 (4)
C130.82739 (14)0.60643 (17)0.49786 (12)0.0258 (5)
H130.82400.69180.49160.031*
C140.79515 (14)0.55355 (17)0.55848 (12)0.0258 (4)
H140.76920.60320.59270.031*
C150.93708 (15)0.51553 (18)0.33043 (13)0.0316 (5)
H15A0.89720.44450.30970.047*
H15B1.00060.48940.36440.047*
H15C0.94290.56350.28290.047*
C160.91164 (16)0.71857 (17)0.38199 (13)0.0332 (5)
H16A0.85210.76270.37610.050*
H16B0.93640.73920.33530.050*
H16C0.95870.74090.43500.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0461 (9)0.0199 (7)0.0374 (8)−0.0033 (6)0.0201 (7)−0.0016 (6)
N10.0568 (13)0.0308 (10)0.0438 (11)0.0060 (9)0.0286 (10)0.0004 (8)
N20.0349 (10)0.0210 (8)0.0292 (9)0.0003 (7)0.0159 (8)0.0011 (7)
C10.0485 (15)0.0406 (13)0.0372 (13)0.0114 (11)0.0252 (12)0.0032 (10)
C20.0320 (12)0.0370 (12)0.0291 (11)−0.0004 (9)0.0152 (9)0.0073 (9)
C30.0316 (11)0.0232 (10)0.0268 (11)−0.0005 (9)0.0083 (9)0.0011 (8)
C40.0254 (10)0.0241 (10)0.0228 (10)0.0011 (8)0.0069 (8)0.0009 (8)
C50.0373 (12)0.0242 (10)0.0307 (11)0.0013 (9)0.0170 (10)0.0012 (8)
C60.0268 (11)0.0210 (10)0.0245 (10)−0.0036 (8)0.0079 (9)−0.0016 (8)
C70.0311 (11)0.0207 (10)0.0295 (11)0.0012 (8)0.0105 (9)0.0016 (8)
C80.0302 (11)0.0196 (9)0.0262 (10)−0.0024 (8)0.0099 (9)−0.0016 (8)
C90.0231 (10)0.0207 (9)0.0248 (10)−0.0010 (8)0.0084 (8)−0.0013 (8)
C100.0318 (11)0.0179 (9)0.0289 (11)−0.0004 (8)0.0106 (9)−0.0005 (8)
C110.0292 (11)0.0211 (10)0.0281 (10)0.0001 (8)0.0119 (9)−0.0046 (8)
C120.0216 (10)0.0226 (10)0.0231 (10)−0.0014 (8)0.0065 (8)−0.0003 (8)
C130.0315 (11)0.0163 (9)0.0311 (11)0.0000 (8)0.0115 (9)−0.0004 (8)
C140.0285 (11)0.0216 (9)0.0302 (11)0.0024 (8)0.0130 (9)−0.0023 (8)
C150.0349 (12)0.0307 (11)0.0335 (11)−0.0019 (9)0.0164 (10)0.0003 (9)
C160.0405 (13)0.0233 (10)0.0394 (12)−0.0023 (9)0.0174 (10)0.0045 (9)
Geometric parameters (Å, °) top
O1—C61.238 (2)C8—C91.443 (2)
N1—C11.338 (3)C8—H80.9500
N1—C51.343 (2)C9—C101.401 (2)
N2—C121.367 (2)C9—C141.405 (3)
N2—C151.453 (2)C10—C111.371 (3)
N2—C161.463 (2)C10—H100.9500
C1—C21.378 (3)C11—C121.411 (2)
C1—H10.9500C11—H110.9500
C2—C31.365 (3)C12—C131.411 (3)
C2—H20.9500C13—C141.370 (3)
C3—C41.390 (3)C13—H130.9500
C3—H30.9500C14—H140.9500
C4—C51.394 (3)C15—H15A0.9800
C4—C61.492 (2)C15—H15B0.9800
C5—H50.9500C15—H15C0.9800
C6—C71.458 (3)C16—H16A0.9800
C7—C81.342 (2)C16—H16B0.9800
C7—H70.9500C16—H16C0.9800
C1—N1—C5116.96 (18)C10—C9—C8119.74 (17)
C12—N2—C15120.43 (15)C14—C9—C8123.82 (17)
C12—N2—C16120.01 (16)C11—C10—C9122.61 (17)
C15—N2—C16116.07 (16)C11—C10—H10118.7
N1—C1—C2123.9 (2)C9—C10—H10118.7
N1—C1—H1118.1C10—C11—C12120.76 (18)
C2—C1—H1118.1C10—C11—H11119.6
C3—C2—C1118.4 (2)C12—C11—H11119.6
C3—C2—H2120.8N2—C12—C13121.80 (16)
C1—C2—H2120.8N2—C12—C11121.30 (17)
C2—C3—C4120.10 (18)C13—C12—C11116.87 (17)
C2—C3—H3120.0C14—C13—C12121.51 (17)
C4—C3—H3120.0C14—C13—H13119.2
C3—C4—C5117.36 (18)C12—C13—H13119.2
C3—C4—C6119.39 (17)C13—C14—C9121.77 (18)
C5—C4—C6123.24 (17)C13—C14—H14119.1
N1—C5—C4123.34 (19)C9—C14—H14119.1
N1—C5—H5118.3N2—C15—H15A109.5
C4—C5—H5118.3N2—C15—H15B109.5
O1—C6—C7122.12 (17)H15A—C15—H15B109.5
O1—C6—C4118.59 (17)N2—C15—H15C109.5
C7—C6—C4119.28 (16)H15A—C15—H15C109.5
C8—C7—C6121.66 (17)H15B—C15—H15C109.5
C8—C7—H7119.2N2—C16—H16A109.5
C6—C7—H7119.2N2—C16—H16B109.5
C7—C8—C9128.46 (18)H16A—C16—H16B109.5
C7—C8—H8115.8N2—C16—H16C109.5
C9—C8—H8115.8H16A—C16—H16C109.5
C10—C9—C14116.44 (17)H16B—C16—H16C109.5
C5—N1—C1—C20.3 (3)C7—C8—C9—C142.9 (3)
N1—C1—C2—C3−0.1 (3)C14—C9—C10—C11−1.5 (3)
C1—C2—C3—C4−0.4 (3)C8—C9—C10—C11178.42 (18)
C2—C3—C4—C50.8 (3)C9—C10—C11—C120.6 (3)
C2—C3—C4—C6−179.95 (18)C15—N2—C12—C13176.60 (17)
C1—N1—C5—C40.1 (3)C16—N2—C12—C1318.5 (3)
C3—C4—C5—N1−0.6 (3)C15—N2—C12—C11−5.1 (3)
C6—C4—C5—N1−179.85 (19)C16—N2—C12—C11−163.19 (18)
C3—C4—C6—O1−15.8 (3)C10—C11—C12—N2−177.40 (18)
C5—C4—C6—O1163.44 (19)C10—C11—C12—C131.0 (3)
C3—C4—C6—C7162.98 (18)N2—C12—C13—C14176.66 (18)
C5—C4—C6—C7−17.8 (3)C11—C12—C13—C14−1.7 (3)
O1—C6—C7—C8−0.4 (3)C12—C13—C14—C90.8 (3)
C4—C6—C7—C8−179.08 (18)C10—C9—C14—C130.8 (3)
C6—C7—C8—C9179.34 (18)C8—C9—C14—C13−179.16 (18)
C7—C8—C9—C10−177.03 (19)
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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