(E)-1-(4-Methoxyanthracen-1-yl)-2-phenyldiazene

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( E )-1-(4-Methoxyanthracen-1-yl)-2- phenyldiazene

Aurelien Crochet,^aKatharina M. Fromm,^a* Vanya Kurteva^band Liudmil Antonov^b*

aUniversity of Fribourg, Department of Chemistry, Chemin du Musee 9, CH-1700 Fribourg, Switzerland, and^bInstitute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bdg 9, Sofia 1113, Bulgaria

Correspondence e-mail: [email protected], [email protected] Received 10 February 2011; accepted 23 March 2011

Key indicators: single-crystal X-ray study;T= 150 K; mean(C–C) = 0.004 A˚;

Rfactor = 0.047;wRfactor = 0.086; data-to-parameter ratio = 11.9.

The title compound, C21H16N2O, has anE-conformation about the diazene N N bond. It is reasonably planar with the phenyl ring being inclined to the mean plane of the anthracene moiety [planar to within 0.077 (3) A˚ ] by 6.43 (10). The crystal structure is stabilized by C—H and weak–interactions [centroid–centroid distances of 3.7192 (16) and 3.8382 (15) A˚ ], leading to the formation of two-dimensional networks stacking along [001] and lying parallel to (110).

Related literature

For background to sensing molecules based on tautomeric switches, see: Nedeltchevaet al.(2009); Antonovet al.(2009, 2010). For investigations of the tautomerism of azodyes, see:

Kelemen (1981). For the synthesis of the title compound, see:

Nedeltchevaet al.(2010).

Experimental

Crystal data

C21H16N2O M_r= 312.36

Orthorhombic,P212121

a= 6.3021 (3) A˚ b= 9.0481 (4) A˚ c= 27.3935 (17) A˚ V= 1562.03 (14) A˚³

Z= 4

MoKradiation = 0.08 mm¹ T= 150 K

0.540.320.12 mm

Data collection

STOE IPDS 2T diffractometer 12181 measured reﬂections 2584 independent reﬂections

2096 reﬂections withI> 2(I) Rint= 0.072

Reﬁnement

R[F²> 2(F²)] = 0.047 wR(F²) = 0.086 S= 1.10 2584 reﬂections

218 parameters

H-atom parameters constrained max= 0.13 e A˚³

min=0.15 e A˚³

Table 1

C—H interactions (A˚ ,).

Cg1,Cg2 andCg3 are the centroids of the C1–C6, C7,C8,C17–C20 and C8–

C10,C15–C17) rings, respectively.

C—H Cg C—H H Cg C Cg C—H Cg

C21—H21A Cg1ⁱ 0.98 2.83 3.646 (4) 141

C12—H12 Cg2ⁱⁱ 0.95 2.80 3.681 (4) 154

C11—H11 Cg3ⁱⁱ 0.95 2.83 3.543 (3) 132

Symmetry codes: (i)xþ1;yþ1;z; (ii)xþ2;yþ¹2;zþ¹2.

Data collection:X-AREA(Stoe & Cie, 2009); cell reﬁnement:X- AREA; data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97(Sheldrick, 2008); program(s) used to reﬁne structure: SHELXL97 (Sheldrick, 2008); molecular graphics:PLATON(Spek, 2009) andMercury(Macraeet al., 2006);

software used to prepare material for publication: SHELXL97, PLATONandpublCIF(Westrip, 2010).

The authors thank the Bulgarian National Science Fund (Project TK–X-1716), the SCOPES program of the Swiss National Science Foundation and FriMat for generous funding. They also thank Professor Helen Stoekli-Evans for valuable advice and assistance.

Supplementary data and ﬁgures for this paper are available from the IUCr electronic archives (Reference: NC2221).

References

Antonov, L., Deneva, V., Simeonov, S., Kurteva, V., Nedeltcheva, D. & Wirz, J.

(2009).Angew. Chem. Int. Ed.48, 7875–7878.

Antonov, L. M., Kurteva, V. B., Simeonov, S. P., Deneva, V. V., Crochet, A. &

Fromm, K. (2010).Tetrahedron,66, 4292–4297.

Kelemen, J. (1981).J. Dyes Pigm.2, 73–91.

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).J. Appl. Cryst.39, 453–457.

Nedeltcheva, D., Antonov, L., Lycka, A., Damyanova, B. & Popov, S. (2009).

Curr. Org. Chem.13, 217–240.

Nedeltcheva, D., Kurteva, V. & Topalova, I. (2010).Rapid Commun. Mass Spectrom.24, 714–720.

Sheldrick, G. M. (2008).Acta Cryst.A64, 112–122.

Spek, A. L. (2009).Acta Cryst.D65, 148–155.

Stoe & Cie (2009).X-AREAandX-RED32. Stoe & Cie GmbH, Darmstadt, Germany.

Westrip, S. P. (2010).J. Appl. Cryst.43, 920–925.

organic compounds

Acta Cryst.(2011). E67, o993 doi:10.1107/S1600536811010932 Crochetet al.

o993

Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

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(E)-1-(4-Methoxyanthracen-1-yl)-2-phenyldiazene