organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1066

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

aDepartment of Physics, Mangalore Institute of Technology and Engineering, Badagamijar, Moodabidri 574 225, India, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 13 April 2009; accepted 14 April 2009; online 18 April 2009)

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.

Related literature

For 3-(4-chloro­phenyl)-1-(3-pyridyl)prop-2-en-1-one, which crystallizes in a non-centrosymmetric space group, see: Uchida et al. (1998[Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abdureyim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135-140.]). For the general synthesis by the Claisen–Schmidt condensation, see: Vogel (1999[Vogel, A. I. (1999). Vogel's Textbook of Practical Organic Chemistry, 5th ed., p. 1033. London: Longman.]). For literature on related compounds exhibiting second-harmonic generation activity, see: Gu et al. (2008[Gu, B., Ji, W., Patil, P. S. & Dharmaprakash, S. M. (2008). J. Appl. Phys. 103, 103511-103516.]); Ravindra et al. (2008a[Ravindra, H. J., Kiran, A. J., Satheesh, R. N., Dharmaprakash, S. M., Chandrasekharan, K., Balakrishna, K. & Rotermund, F. (2008a). J. Cryst. Growth, 310, 2543-2549.],b[Ravindra, H. J., Kiran, A. J., Satheesh, R. N., Dharmaprakash, S. M., Chandrasekharan, K., Balakrishna, K. & Rotermund, F. (2008b). J. Cryst. Growth, 310, 4169-4176.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O

  • Mr = 252.31

  • Monoclinic, C 2/c

  • a = 14.6672 (6) Å

  • b = 11.0644 (4) Å

  • c = 16.7272 (6) Å

  • β = 107.205 (3)°

  • V = 2593.1 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.20 × 0.20 × 0.03 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 11747 measured reflections

  • 2976 independent reflections

  • 1817 reflections with I > 2˘I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.147

  • S = 1.02

  • 2976 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ω scansh = 1918
11747 measured reflectionsk = 1414
2976 independent reflectionsl = 2121
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 Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H16N2OV = 2593.1 (2) Å3
Mr = 252.31Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.6672 (6) ŵ = 0.08 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.02Δρmax = 0.22 e Å3
2976 reflectionsΔρmin = 0.28 e Å3
174 parameters
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, º) 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—C30.1 (3)C14—C9—C10—C111.5 (3)
C1—C2—C3—C40.4 (3)C8—C9—C10—C11178.42 (18)
C2—C3—C4—C50.8 (3)C9—C10—C11—C120.6 (3)
C2—C3—C4—C6179.95 (18)C15—N2—C12—C13176.60 (17)
C1—N1—C5—C40.1 (3)C16—N2—C12—C1318.5 (3)
C3—C4—C5—N10.6 (3)C15—N2—C12—C115.1 (3)
C6—C4—C5—N1179.85 (19)C16—N2—C12—C11163.19 (18)
C3—C4—C6—O115.8 (3)C10—C11—C12—N2177.40 (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—C717.8 (3)C11—C12—C13—C141.7 (3)
O1—C6—C7—C80.4 (3)C12—C13—C14—C90.8 (3)
C4—C6—C7—C8179.08 (18)C10—C9—C14—C130.8 (3)
C6—C7—C8—C9179.34 (18)C8—C9—C14—C13179.16 (18)
C7—C8—C9—C10177.03 (19)

Experimental details

Crystal data
Chemical formulaC16H16N2O
Mr252.31
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)14.6672 (6), 11.0644 (4), 16.7272 (6)
β (°) 107.205 (3)
V3)2593.1 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.20 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11747, 2976, 1817
Rint0.063
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.147, 1.02
No. of reflections2976
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGu, B., Ji, W., Patil, P. S. & Dharmaprakash, S. M. (2008). J. Appl. Phys. 103, 103511–103516.  Web of Science CrossRef Google Scholar
First citationRavindra, H. J., Kiran, A. J., Satheesh, R. N., Dharmaprakash, S. M., Chandrasekharan, K., Balakrishna, K. & Rotermund, F. (2008a). J. Cryst. Growth, 310, 2543–2549.  Web of Science CrossRef CAS Google Scholar
First citationRavindra, H. J., Kiran, A. J., Satheesh, R. N., Dharmaprakash, S. M., Chandrasekharan, K., Balakrishna, K. & Rotermund, F. (2008b). J. Cryst. Growth, 310, 4169–4176.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abdureyim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140.  Web of Science CrossRef Google Scholar
First citationVogel, A. I. (1999). Vogel's Textbook of Practical Organic Chemistry, 5th ed., p. 1033. London: Longman.  Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1066
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