(IUCr) N,N'-Bis(1-ethynylcyclohexyl)pyromellitic diimide

Volume 65
Part 9
Page o2122
September 2009

Received 14 July 2009
Accepted 4 August 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.065
wR = 0.158
Data-to-parameter ratio = 13.8
Details

N,N'-Bis(1-ethynylcyclohexyl)pyromellitic diimide

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, England
Correspondence e-mail: hamilton@mtholyoke.edu

The title compound, C₂₆H₂₄N₂O₄, consists of a symmetrical molecule that lies across a crystallographic inversion centre. The C-C distance in the triple bond is 1.188 (2) Å and there is also an intermolecular C-HO contact from a terminal acetylene C-H to one of the dimiide O atoms [3.4349 (19) Å].

Related literature

For literature relating to the oxidative coupling of terminal acetylenes, see: Anderson, Anderson & Sanders (1995); Anderson, Walter et al. (1995); Hamilton et al. (1998); Raehm et al. (2002).

Experimental

Crystal data

C₂₆H₂₄N₂O₄
M_r = 428.47
Monoclinic, P 2₁ /c
a = 13.1774 (3) Å
b = 7.1519 (1) Å
c = 11.8104 (3) Å
= 112.495 (1)°
V = 1028.36 (4) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 120 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.963, T_max = 0.982
12939 measured reflections
2022 independent reflections
1898 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.158
S = 1.29
2022 reflections
146 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.80 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H12O2ⁱ	0.95	2.52	3.4349 (19)	161
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: PLATON97 (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: ZS2003 ).

Acknowledgements

We thank the National Science Foundation (award No. 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, England) for their support of this work.

References

Anderson, S., Anderson, H. L. & Sanders, J. K. M. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 2255-2267.
Anderson, H. L., Walter, C. J., VidalFerran, A., Hay, R. A., Lowden, P. A. & Sanders, J. K. M. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 2275-2279.
Hamilton, D. G., Davies, J. E., Prodi, L. & Sanders, J. K. M. (1998). Chem. Eur. J. 4, 608-620.
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. Version 2.10. 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