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

Hanton, L.R.; Moratti, S.C.; Shi, Z.; Simpson, J.

doi:10.1107/S1600536810018994

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 (C-C) = 0.005 Å
R = 0.054
wR = 0.152
Data-to-parameter ratio = 7.8
Details

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

Lyall R. Hanton,^a Stephen C. Moratti,^a Zheng Shi ^a and Jim Simpson ^a ^*

^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-N_pip 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-HO hydrogen bonds link adjacent molecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-HO 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, 2010); Flood et al. (2007). For their incorporation into polymer systems, see: Dana et al. (2007); Munro et al. (2008). For related structures, see: McAdam et al. (2003); Easton et al. (1992); Batchelor et al. (1997); Tagg et al. (2008). For comparative bond-length data, see: Allen et al. (1987) and for ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₁H₂₀N₂O₃
M_r = 348.39
Monoclinic, C 2/c
a = 29.049 (3) Å
b = 6.9852 (7) Å
c = 17.1503 (17) Å
= 102.013 (6)°
V = 3403.7 (6) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.838, T_max = 1.000
12211 measured reflections
1843 independent reflections
1440 reflections with I > 2(I)
R_int = 0.075
_max = 21.2°

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.152
S = 1.12
1843 reflections
236 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C21-H21BO12ⁱ	0.99	2.54	3.485 (4)	160
C24-H24AO12ⁱⁱ	0.99	2.67	3.365 (4)	127
C21-H21AO11ⁱⁱⁱ	0.99	2.36	3.258 (4)	150
C25-H25BO11^iv	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); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
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.
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.
Dana, B. H., McAdam, C. J., Robinson, B. H., Simpson, J. & Wang, H. (2007). J. Inorg. Organomet. Polym. Mater. 17, 547-559.
Easton, C. J., Gulbis, J. M., Hoskins, B. F., Scharfbillig, I. M. & Tiekink, E. R. T. (1992). Z. Kristallogr. 199, 249-254.
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.
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.
McAdam, C. J., Morgan, J. L., Robinson, B. H., Simpson, J., Rieger, P. H. & Rieger, A. L. (2003). Organometallics, 22, 5126- 5136.
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 .
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tagg, T., McAdam, C. J., Robinson, B. H. & Simpson, J. (2008). Acta Cryst. C64, o388-o391.
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References