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Volume 66 
Part 6 
Pages o1476-o1477  
June 2010  

Received 20 May 2010
Accepted 20 May 2010
Online 29 May 2010

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.005 Å
R = 0.054
wR = 0.152
Data-to-parameter ratio = 7.8
Details
Open access

N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide

aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
Correspondence e-mail: jsimpson@alkali.otago.ac.nz

In the title compound, C21H20N2O3, the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). The carboximide N atom and the five C atoms of the 2-methylprop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84.34 (7)° to the naphthalamide plane. This orients the =CH2 group of the vinyl fragment towards the naphthalimide rings, giving the molecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C-Npip bond length being 1.404 (4) Å. In the crystal structure, [pi]-[pi] contacts with centroid-centroid distances of 3.5351 (18) and 3.7794 (18) Å supported by C-H...O hydrogen bonds link adjacent molecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-H...O contacts of varying strength, which stack the molecules down the b axis.

Related literature

For background to the applications of 1,8-naphthalamides, see: McAdam et al. (2003[McAdam, C. J., Morgan, J. L., Robinson, B. H., Simpson, J., Rieger, P. H. & Rieger, A. L. (2003). Organometallics, 22, 5126- 5136.], 2010[McAdam, C. J., Robinson, B. H., Simpson, J. & Tagg, T. (2010). Organometallics, doi: 10.1021/om1000452.]); Flood et al. (2007[Flood, A. H., McAdam, C. J., Gordon, K. C., Kjaergaard, H. G., Manning, A. R., Robinson, B. H. & Simpson, J. (2007). Polyhedron, 26, 448-455.]). For their incorporation into polymer systems, see: Dana et al. (2007[Dana, B. H., McAdam, C. J., Robinson, B. H., Simpson, J. & Wang, H. (2007). J. Inorg. Organomet. Polym. Mater. 17, 547-559.]); Munro et al. (2008[Munro, N. H., Hanton, L. R., Robinson, B. H. & Simpson, J. (2008). React. Funct. Polym. 68 671-678 .]). For related structures, see: McAdam et al. (2003[McAdam, C. J., Morgan, J. L., Robinson, B. H., Simpson, J., Rieger, P. H. & Rieger, A. L. (2003). Organometallics, 22, 5126- 5136.]); Easton et al. (1992[Easton, C. J., Gulbis, J. M., Hoskins, B. F., Scharfbillig, I. M. & Tiekink, E. R. T. (1992). Z. Kristallogr. 199, 249-254.]); Batchelor et al. (1997[Batchelor, R. A., Hunter, C. A. & Simpson, J. (1997). Acta Cryst. C53, 1117-1119.]); Tagg et al. (2008[Tagg, T., McAdam, C. J., Robinson, B. H. & Simpson, J. (2008). Acta Cryst. C64, o388-o391.]). For comparative bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]) and for ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20N2O3

  • Mr = 348.39

  • Monoclinic, C 2/c

  • a = 29.049 (3) Å

  • b = 6.9852 (7) Å

  • c = 17.1503 (17) Å

  • [beta] = 102.013 (6)°

  • V = 3403.7 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 90 K

  • 0.65 × 0.11 × 0.04 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.838, Tmax = 1.000

  • 12211 measured reflections

  • 1843 independent reflections

  • 1440 reflections with I > 2[sigma](I)

  • Rint = 0.075

  • [theta]max = 21.2°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.152

  • S = 1.12

  • 1843 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21B...O12i 0.99 2.54 3.485 (4) 160
C24-H24A...O12ii 0.99 2.67 3.365 (4) 127
C21-H21A...O11iii 0.99 2.36 3.258 (4) 150
C25-H25B...O11iv 0.99 2.72 3.278 (4) 117
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iv) [-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. 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.]) and TITAN2000 (Hunter & Simpson, 1999[Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5457 ).


Acknowledgements

We thank the New Economy Research Fund; grant No. UOO-X0808 for support of this work and the University of Otago for purchase of the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Batchelor, R. A., Hunter, C. A. & Simpson, J. (1997). Acta Cryst. C53, 1117-1119.  [CrossRef] [details]
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dana, B. H., McAdam, C. J., Robinson, B. H., Simpson, J. & Wang, H. (2007). J. Inorg. Organomet. Polym. Mater. 17, 547-559.  [CrossRef] [ChemPort]
Easton, C. J., Gulbis, J. M., Hoskins, B. F., Scharfbillig, I. M. & Tiekink, E. R. T. (1992). Z. Kristallogr. 199, 249-254.  [ChemPort]
Flood, A. H., McAdam, C. J., Gordon, K. C., Kjaergaard, H. G., Manning, A. R., Robinson, B. H. & Simpson, J. (2007). Polyhedron, 26, 448-455.  [ISI] [CrossRef] [ChemPort]
Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
McAdam, C. J., Morgan, J. L., Robinson, B. H., Simpson, J., Rieger, P. H. & Rieger, A. L. (2003). Organometallics, 22, 5126- 5136.  [CSD] [CrossRef] [ChemPort]
McAdam, C. J., Robinson, B. H., Simpson, J. & Tagg, T. (2010). Organometallics, doi: 10.1021/om1000452.
Munro, N. H., Hanton, L. R., Robinson, B. H. & Simpson, J. (2008). React. Funct. Polym. 68 671-678 .  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tagg, T., McAdam, C. J., Robinson, B. H. & Simpson, J. (2008). Acta Cryst. C64, o388-o391.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.


Acta Cryst (2010). E66, o1476-o1477   [ doi:10.1107/S1600536810018994 ]

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