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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

2-(4-Bromophenyl)-8-cyano-5,7-dimethyloxazolo[3,2-a]pyridin-1-ylium perchlorate

Dmitry V. Albov,* Eugenia I. Turubanova, Victor B. Rybakov, Eugene V. Babaev and Leonid A. Aslanov
Department of Chemistry, Moscow State University, 119992 Moscow, Russian Federation Correspondence e-mail: albov@biocryst.phys.msu.su

The title compound, C16H12BrN2O+āClO4ū, was synthesized, and characterized by 1H NMR and X-ray diffraction techniques.

Received 22 June 2004 Accepted 30 June 2004 Online 9 July 2004

Comment
We have described earlier the crystal structure of N-(4bromophenacyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-2carbonitrile, (1) (Albov et al., 2004). Now, we report here the synthesis and crystal structure of the title compound, (2).

Key indicators Single-crystal X-ray study T = 293 K é Mean ' (CąC) = 0.004 A R factor = 0.045 wR factor = 0.132 Data-to-parameter ratio = 14.4 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

An analysis of bond lengths in the oxazolopyridinium ring system of (2) (Fig. 1) shows its aromaticity. The nineé membered bicyclic system is planar to within 0.018 (2) A; atoms C61, C71, C91 and C10 lie in the same plane. The é benzene ring is planar to within 0.007 (2) A, with atoms Br1 and C2 in the same plane. The dihedral angle between the oxazolopyridinium and benzene fragments is 2.62 (7) , indicating that there is considerable conjugation between these aromatic fragments.

Experimental
For the preparation of (2), compound (1) (0.5 g, 1.448 mmol) was dissolved in 20 ml of sulfuric acid and the reaction mixture was allowed to stand for 5 min. It was then poured into a mixture of 100 ml of water and 5 ml of a 70% solution of perchloric acid. The resulting precipitate was Žltered off, washed with water and dried in air (yield 0.51 g, 82%; m.p. 512 514 K). The compound was recrys tallized from acetonitrile. 1H NMR (DMSO d6, 400 MHz, p.p.m.): 2.86 (s, 3H, 5 CH3), 3.05 (s, 3H, 5 CH3), 8.0 (s, 1H, 6 CH), 7.82 7.84, 7.88 8.02 (dd, 4H, Ar), 9.6 (s, 1H, 3 CH). Crystal data
C16H12BrN2O+āClO4 Mr = 427.64 Triclinic, P1 é a = 7.150 (3) A é b = 7.800 (2) A é c = 15.481 (5) A = 90.68 (2) = 102.62 (3) = 98.48 (3) é V = 832.4 (5) A3 DOI: 10.1107/S1600536804015995 Z=2 Dx = 1.706 Mg m 3 Cu K radiation Cell parameters from 25 re¯ections = 32 35 " = 5.13 mm 1 T = 293 (2) K Prism, yellow 0.30 á 0.30 á 0.30 mm Dmitry V. Albov et al.


# 2004 International Union of Crystallography Printed in Great Britain ą all rights reserved

Acta Cryst. (2004). E60, o1303ąo1304

C16H12BrN2O+āClO4

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organic papers
Data collection
Enraf Nonius CAD-4 diffractometer Non-proŽled 3 scans Absorption correction: none 3288 measured re¯ections 3288 independent re¯ections 2825 re¯ections with I > 2' (I) max = 74.8 h= 838 k= 939 l = 0 3 19 1 standard re¯ection frequency: 60 min intensity decay: 2% w = 1/[' 2(Fo2) + (0.0738P)2 + 0.5105P] where P = (Fo2 + 2Fc2)/3 (ā/' )max < 0.001 é ā&max = 0.35 e A 3 é ā&min = 0.47 e A 3

ReŽnement
ReŽnement on F 2 R[F 2 > 2' (F 2)] = 0.045 wR(F 2) = 0.132 S = 1.06 3288 re¯ections 228 parameters H-atom parameters constrained

Figure 1

Table 1

ORTEP 3 (Farrugia, 1997) plot of (2), with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

é Selected geometric parameters (A, ).
Br1īC13 N1īC5 N1īC9 N1īC2 C2īC3 C3īO4 C3īC10 O4īC5 C5īC6 C6īC7 C6īC61 C7īC8 C7īC71 C5īN1īC9 C5īN1īC2 C9īN1īC2 C3īC2īN1 C2īC3īO4 C2īC3īC10 O4īC3īC10 C5īO4īC3 O4īC5īN1 O4īC5īC6 N1īC5īC6 C5īC6īC7 C5īC6īC61 C7īC6īC61 C6īC7īC8 C6īC7īC71 C8īC7īC71 C9īC8īC7 C8īC9īN1 1.895 1.348 1.383 1.398 1.338 1.405 1.450 1.328 1.390 1.396 1.426 1.406 1.494 122.0 107.8 130.2 106.7 108.8 133.9 117.3 106.7 110.0 127.7 122.3 117.4 119.8 122.8 118.7 120.4 120.9 123.1 116.5 (3) (3) (4) (4) (4) (3) (4) (4) (4) (4) (4) (4) (4) (3) (2) (2) (2) (3) (3) (2) (2) (2) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) C8īC9 C9īC91 C10īC11 C10īC15 C11īC12 C12īC13 C13īC14 C14īC15 C61īN61 Cl1īO14 Cl1īO13 Cl1īO11 Cl1īO12 C8īC9īC91 N1īC9īC91 C11īC10īC15 C11īC10īC3 C15īC10īC3 C12īC11īC10 C11īC12īC13 C12īC13īC14 C12īC13īBr1 C14īC13īBr1 C15īC14īC13 C14īC15īC10 N61īC61īC6 O14īCL1īO13 O14īCL1īO11 O13īCL1īO11 O14īCL1īO12 O13īCL1īO12 O11īCL1īO12 1.370 1.476 1.393 1.394 1.373 1.375 1.385 1.373 1.140 1.408 1.414 1.415 1.418 126.6 116.9 118.9 119.4 121.7 120.6 119.5 121.0 119.4 119.6 119.4 120.5 178.0 110.2 107.2 109.8 109.8 109.9 109.9 (4) (4) (4) (4) (5) (5) (5) (5) (4) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (3) (4) (2) (2) (2) (3) (2) (3)

H atoms were included in calculated positions (C H 0.93 é 0.96 A) and reŽned as riding, with Uiso(H) 1.5Ueq(methyl C) or 1.2Ueq(C) (others). Data collection: CAD 4 EXPRESS (Enraf Nonius, 1994); cell reŽnement: CAD 4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to reŽne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP 3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

The authors are indebted to the Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database (Allen, 2002) (project No. 0207-90322).

References
Albov, D. V., Turubanova, E. I., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004). Acta Cryst. E60, o1222 o1223. Allen, F. H. (2002). Acta Cryst. B58, 380 388. Enraf Nonius (1994). CAD-4 EXPRESS. Version 5.0. Enraf Nonius, Delft, The Netherlands. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837 838. Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of õ Gottingen, Germany.

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Dmitry V. Albov et al.



C16H12BrN2O+āClO4

Acta Cryst. (2004). E60, o1303ąo1304