2,2′,2′′-[Nitrilo­tris(methyl­ene-p-phenyl­ene)]tribenzonitrile

Chen, L.-Z.

doi:10.1107/S1600536808029784

Volume 64
Part 10
Page o1980
October 2008

Received 29 August 2008
Accepted 16 September 2008
Online 20 September 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.066
wR = 0.188
Data-to-parameter ratio = 18.1
Details

2,2',2''-[Nitrilotris(methylene-p-phenylene)]tribenzonitrile

Li-Zhuang Chen ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: clz1977@sina.com

In the title compound, C₄₂H₃₀N₄, the conformations of the three wings of the molecule are not similar to each other as the torsion angles between the planes of the benzene rings are significantly different. In addition to van der Waals interactions, the crystal structure is stabilized only by intramolecular C-HN hydrogen bonds.

Related literature

For related structures, see: Fox et al. (1996); Menage et al. (1992); Murthy & Karlin (1993); Schrock (1997); Foces-Foces et al. (1999); Chen et al. (2005); Iwasaki & Iwasaki (1972).

Experimental

Crystal data

C₄₂H₃₀N₄
M_r = 590.70
Monoclinic, P 2₁ /c
a = 21.257 (4) Å
b = 15.085 (3) Å
c = 10.294 (2) Å
= 94.73 (3)°
V = 3289.5 (11) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 298 (2) K
0.27 × 0.18 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.985, T_max = 0.989
32746 measured reflections
7524 independent reflections
4007 reflections with I > 2(I)
R_int = 0.081

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.187
S = 1.02
7524 reflections
415 parameters
6 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4AN3ⁱ	0.93	2.55	3.446 (5)	162
C24-H24AN2ⁱⁱ	0.93	2.59	3.350 (4)	139
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2103 ).

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

Chen, Q., Buss, C. E., Young, V. G. Jr & Fox, S. (2005). J. Chem. Crystallogr. 35, 177-181.
Foces-Foces, C., Llamas-Saiz, A. L., Alajarín, M., López-Lázaro, A. & Molina, P. (1999). Acta Cryst. C55, 373-377.
Fox, S., Nanthakumar, A., Wikström, M., Karlin, K. D. & Blackburn, N. J. (1996). J. Am. Chem. Soc. 118, 24-34.
Iwasaki, F. & Iwasaki, H. (1972). Acta Cryst. B28, 3370-3376.
Menage, S., Zang, Y., Hendrich, M. P. & Que, L. Jr (1992). J. Am. Chem. Soc. 114, 7786-7792.
Murthy, N. N. & Karlin, K. D. (1993). J. Am. Chem. Soc. 115, 1236-1238.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Schrock, R. R. (1997). Acc. Chem. Res. 30, 9-16.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds