(IUCr) N,N'-Bis(1-acetylcyclohexyl)-1,8:4,5-naphthalenetetracarboximide

Volume 65
Part 9
Page o2184
September 2009

Received 4 August 2009
Accepted 13 August 2009
Online 19 August 2009

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.063
wR = 0.150
Data-to-parameter ratio = 13.8
Details

N,N'-Bis(1-acetylcyclohexyl)-1,8:4,5-naphthalenetetracarboximide

Chenaimwoyo A. Gondo,^a Daniel E. Lynch ^b and Darren G. Hamilton ^a ^*

^aDepartment of Chemistry, Mount Holyoke College, South Hadley, Masssachusetts 01075, USA, and ^bExilica Limited, The Technocentre, Puma Way, Coventry CV1 2TT, UK
Correspondence e-mail: hamilton@mtholyoke.edu

The title compound, C₃₀H₃₀N₂O₆, has crystallographic inversion symmetry with the nitrogen atom and the two oxygen atoms of the naphthalene diimide system deviating by -0.243 (2), 0.109 (3) and 0.247 (2) Å, respectively, from the plane defined by the carbon atoms.

Related literature

For the structure of a related benzene diimide derivative with terminal acetylene groups, see: Gondo et al. (2009). For preparative procedures for compounds of this type and for the title compound, see Hamilton et al. (1998, 1999); Raehm et al. (2002); Ahn et al. (1997).

Experimental

Crystal data

C₃₀H₃₀N₂O₆
M_r = 514.56
Monoclinic, P 2₁ /c
a = 5.8553 (2) Å
b = 13.6603 (6) Å
c = 15.2820 (6) Å
= 94.001 (2)°
V = 1219.35 (8) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 120 K
0.20 × 0.18 × 0.06 mm

Data collection

Bruker-Nonius 95 mm CCD camera on -goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.981, T_max = 0.994
11932 measured reflections
2397 independent reflections
1949 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.150
S = 1.17
2397 reflections
174 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.59 e Å^-3

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2005 ).

Acknowledgements

We thank the National Science Foundation (Award 0314514), the Camille and Henry Dreyfus Foundation (Henry Dreyfus Teacher Scholar Award to DGH, 2005-2010), and the EPSRC National Crystallography Service (University of Southampton, UK) for their support of this work.

References

Ahn, C., Campbell, R. F. & Feldman, K. S. (1997). Bull. Korean Chem. Soc. 18, 441-442.
Gondo, C. A., Lynch, D. E. & Hamilton, D. G. (2009). Acta Cryst. E65, o2122.
Hamilton, D. G., Davies, J. E., Prodi, L. & Sanders, J. K. M. (1998). Chem. Eur. J. 4, 608-620.
Hamilton, D. G., Prodi, L., Feeder, N. & Sanders, J. K. M. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 1057-1065.
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology. Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Raehm, L., Hamilton, D. G. & Sanders, J. K. M. (2002). Synlett. pp. 1743-1761.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds