1,1′-[2,3,5,6-Tetra­methyl-p-phenyl­ene­bis(methyl­eneoxy)]di-1H-benzotriazole

Ravindran Durai Nayagam, B.; Jebas, S.R.; Daisy, C.; Schollmeyer, D.

doi:10.1107/S1600536809010782

Volume 65
Part 4
Page o918
April 2009

Received 23 March 2009
Accepted 24 March 2009
Online 28 March 2009

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.052
wR = 0.147
Data-to-parameter ratio = 13.6
Details

1,1'-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]di-1H-benzotriazole

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b Caroline Daisy ^a and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India,^bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

The complete molecule of the title compound, C₂₄H₂₄N₆O₂, is generated by a crystallographic inversion centre. The benzotriazole rings form dihedral angles of 2.10 (7)° with the central aromatic ring. The crystal packing is consolidated by [pi] - [pi] interactions, with centroid-centroid distances of 3.6234 (10) Å, together with weak C-H [pi] interactions.

Related literature

For the biological activity of N-oxide and benzotriazole derivatives see: Katarzyna et al.(2005); Sarala et al. (2007). For applications of benzotriazole, see: Kopec et al. (2008); Krawczyk & Gdaniec (2005); Smith et al. (2001); Sha et al. (1996). For 1-hydroxybenzotriazole, see: Anderson et al. (1963); Bosch et al. (1983).

Experimental

Crystal data

C₂₄H₂₄N₆O₂
M_r = 428.49
Monoclinic, P 2₁ /c
a = 9.3895 (6) Å
b = 7.5960 (2) Å
c = 15.7471 (13) Å
= 110.770 (3)°
V = 1050.13 (11) Å³
Z = 2
Cu K radiation
= 0.73 mm^-1
T = 193 K
0.51 × 0.26 × 0.19 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (CORINC; Draeger & Gattow, 1971) T_min = 0.707, T_max = 0.873
2075 measured reflections
1996 independent reflections
1905 reflections with I > 2(I)
R_int = 0.026
3 standard reflections frequency: 60 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.147
S = 1.10
1996 reflections
147 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6Cg2ⁱ	0.95	2.82	3.700 (2)	154
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 is the centroid of the C4-C9 ring.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971); 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: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2912 ).

References

Anderson, G. W., Zimmerman, J. E. & Calahan, F. M. (1963). J. Am. Chem. Soc. 85, 3039-3039.
Bosch, R., Jung, G. & Winter, W. (1983). Acta Cryst. C39, 1089-1092.
Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Katarzyna, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2005). Bioorg. Med. Chem. 13, 3601-3616.
Kopec, E. A., Zwolska, Z. & Kazimierczuk, A. O. Z. (2008). Acta Pol. Pharm. Drug Res. 65, 435-439.
Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967-o2969.
Sarala, G., Swamy, S. N., Prabhuswamy, B., Andalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2007). Anal. Sci. 23, 25-26.
Sha, G., Wang, W. & Ren, T. (1996). Mocha Xuebao, 16, 344-350.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Bottle, S. E., Reid, D. A., Schweinsberg, D. P. & Bott, R. C. (2001). Acta Cryst. E57, o531-o532.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds