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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

2-(4-Chlorophenyl)-5-methyl-7,8-dihydro-6H-cyclopenta[e][1,3]oxazolo[3,2-a]pyridin-9-ium perchlorate

Dmitry V. Albov,* Victor B. Rybakov, Eugene V. Babaev and Leonid A. Aslanov
Department of Chemistry, Moscow State University, 119992 Moscow, Russian Federation Correspondence e-mail: albov@struct.chem.msu.ru

The title compound, C17H15ClNO+āClO4ū, has been synthesized and characterized by 1H NMR and X-ray diffraction techniques. The bicyclic system is aromatic, with positively charged nitrogen, and is conjugated with the benzene ring.

Received 21 September 2004 Accepted 21 October 2004 Online 13 November 2004

Comment
In the course of systematic investigations of the effect of the size of cycloalkane fragments on the reactivity of pyridinebased heterocycles, we have previously described the crystal structure of 4-methyl-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one, (1) (Albov, Mazina et al., 2004). Following a study with cycloheptene derivatives (Albov, Rybakov et al., 2004a,b,c), we synthesized the title compound, (4).

Key indicators Single-crystal X-ray study T = 293 K é Mean ' (CąC) = 0.002 A R factor = 0.045 wR factor = 0.102 Data-to-parameter ratio = 15.0 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 of (4) (Fig. 1 and Table 1) reveals that this bicyclic system is certainly aromatic, with the positive charge located on atom N1. The nine-membered bicyclic system is planar to within é 0.0127 (11) A, with atoms C10, C12, C13 and C14 lying in the same plane. Atom C11 is displaced from this plane by é 0.187 (2) A. The dihedral angle between the oxazolopyridinium and benzene fragments is 4.82 (6) , indicating that there is considerable conjugation between these aromatic fragments. All these results will be compared with crystal structures of other six-, seven- and eight-membered cycloalkane derivatives which are in progress.

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

The title compound was prepared according to the method of Albov, Mazina et al. (2004) (m.p. 571 K, with explosion). 1H NMR (DMSO
doi: 10.1107/S1600536804026777 Dmitry V. Albov et al.


Acta Cryst. (2004). E60, o2313 o2314

C17H15ClNO+āClO4

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organic papers
Table 1
é Selected geometric parameters (A, ).
Cl1īC17 O4īC5 O4īC3 N1īC5 N1īC2 N1īC9 C2īC3 C3īC14 C5īC6 C6īC7 C7īC8 C5īO4īC3 C5īN1īC2 C5īN1īC9 C2īN1īC9 C3īC2īN1 C2īC3īO4 C2īC3īC14 O4īC3īC14 N1īC5īO4 N1īC5īC6 O4īC5īC6 C7īC6īC5 1.7572 (13) 1.3432 (16) 1.3959 (16) 1.3225 (18) 1.4136 (16) 1.4153 (16) 1.3364 (17) 1.4608 (17) 1.3986 (19) 1.347 (2) 1.422 (2) 106.04 109.70 118.66 131.62 104.22 110.59 132.91 116.50 109.40 125.25 125.30 116.49 (10) (10) (11) (11) (11) (11) (11) (10) (11) (13) (13) (14) C7īC13 C8īC9 C8īC10 C9īC12 C10īC11 C11īC12 Cl2īO23 Cl2īO24 Cl2īO22 Cl2īO21 C6īC7īC8 C6īC7īC13 C8īC7īC13 C9īC8īC7 C9īC8īC10 C7īC8īC10 C8īC9īN1 C8īC9īC12 N1īC9īC12 C8īC10īC11 C10īC11īC12 C9īC12īC11 1.499 (2) 1.3461 (19) 1.491 (2) 1.430 (2) 1.538 (3) 1.551 (2) 1.3231 (19) 1.3574 (19) 1.3647 (17) 1.4066 (16) 119.50 120.19 120.32 122.56 108.31 128.96 117.50 117.82 124.50 103.39 107.23 100.52 (12) (14) (13) (13) (13) (13) (13) (13) (12) (13) (13) (13)

Figure 1

ORTEP 3 (Farrugia, 1997) plot of the molecule and atom numbering scheme of compound (4). Displacement ellipsoids are drawn at the 50% probability level.

d6, 400 MHz, p.p.m.): 2.33 (m, 2H, 11 CH2), 2.62 (s, 3H, 13 CH3), 3.17 (t, 2H, 10 CH2), 3.45 (t, 2H, 12 CH2), 7.64, 8.01 (dd, 4H, Ar), 8.04 (s, 1H, 6 CH), 9.33 (s, 1H, 2 CH) (using the crystallographic numbering scheme of Fig. 1). Crystal data
C17H15ClNO+āClO4 Mr = 384.20 Monoclinic, P21 ac é a = 12.631 (5) A é b = 8.329 (5) A é c = 17.982 (8) A = 119.11 (3) é V = 1652.8 (14) A3 Z=4 Dx = 1.544 Mg m 3 Cu K radiation Cell parameters from 25 re¯ections = 25 26 " = 3.80 mm 1 T = 293 (2) K Prism, colourless 0.22 á 0.21 á 0.20 mm max = 74.8 h = 15 3 13 k = 0 3 10 l = 0 3 22 1 standard re¯ection frequency: 30 min intensity decay: 2% H-atom parameters constrained w = 1/[' 2(Fo2) + (0.1086P)2] where P = (Fo2 + 2Fc2)/3 (ā/' )max = 0.001 é ā&max = 0.24 e A 3 é ā&min = 0.29 e A 3

All H atoms were placed in calculated positions and reŽned as é riding atoms, with C H bond lengths in the range 0.93 0.97 A. For methyl H atoms, Uiso values were set equal to 1.5Ueq(C), and for other H atoms to 1.2Ueq(C). 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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (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 (project No. 02-07-90322).

Data collection
Enraf Nonius CAD-4 diffractometer Non-proŽled 3 scans Absorption correction: none 3411 measured re¯ections 3411 independent re¯ections 2899 re¯ections with I > 2' (I)

References
Albov, D. V., Mazina, O. S., Rybakov, V. B., Babaev, E. V., Chernyshev, V. V. & Aslanov, L. A. (2004). Crystallogr. Rep. 49, 158 168. Albov, D. V., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004a). Acta Cryst. E60, o892 o893. Albov, D. V., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004b). Acta Cryst. E60, o894 o895. Albov, D. V., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004c). Acta Cryst. E60, o1096 o1097. Enraf Nonius (1994). CAD-4 Software. 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.

Refinement
ReŽnement on F 2 R[F 2 > 2' (F 2)] = 0.045 wR(F 2) = 0.102 S = 0.79 3411 re¯ections 227 parameters

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Dmitry V. Albov et al.



C17H15ClNO+āClO4

Acta Cryst. (2004). E60, o2313 o2314