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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

1,4-Dimethyl-1,5,6,7-tetrahydro-2Hcyclopenta[b]pyridin-2-one

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@biocryst.phys.msu.su

In the pyridone ring of the title compound, C10H13NO, single and double bonds alternate, though allowing some degree of delocalization.

Received 22 April 2004 Accepted 26 April 2004 Online 30 April 2004

Comment
In the course of our systematic study of the size effect of cycloalkane fragments on the reactivity of pyridine based heterocycles, we have described earlier the crystal structure of 4-methyl-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one, (1) (Albov, Mazina et al., 2004). Our attempt to increase the yield in the reaction of O-methylation (Albov, Rybakov et al., 2004), using excess methyl iodide, caused the subsequent methylation at the N atom and led to the title compound, (2) (Fig. 1).

Key indicators Single-crystal X-ray study T = 293 K é Mean ' (CąC) = 0.002 A R factor = 0.045 wR factor = 0.103 Data-to-parameter ratio = 15.7 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the planar pyridone ring (N1/C9) of (2) the single and double bonds alternate, though allowing some degree of delocalization. Atom C7 is displaced from the plane of the é pyridone ring by 0.179 (2) A. Methylation of the N atom excludes hydrogen bonding and greatly changes the packing, but, in general, the structure of the bicyclic ring systems in (1) and (2) are identical.

Experimental
1,5,6,7 Tetrahydro 2H cyclopenta[b]pyridin 2 one (6.48 g), (1), methyl iodide (12.35 g) and silver carbonate (6.00 g) were boiled in benzene (70 ml) for 50 h. The reaction ¯ask was protected against light. The mixture was then Žltered and the solvent was evaporated (yield 3.14 g, 38%). The product was recrystallized from benzene (m.p. 383 K). 1H NMR (DMSO d6, 400 MHz, p.p.m.): 2.05 (s, 3H, 10 CH3), 2.10 (m, 2H, 7 CH2), 2.68 (t, 2H, 6 CH2), 2.90 (t, 3H, 8 CH3), 3.31 (s, 3H, 11 CH3), 5.96 (s, 1H, 3 CH). Crystal data
C10H13NO Mr = 163.21 Monoclinic, P21 ac é a = 9.7125 (15) A é b = 6.8262 (16) A é c = 15.285 (3) A = 121.233 (11) é V = 866.5 (3) A3 Z=4 Dx = 1.251 Mg m 3 Cu K radiation Cell parameters from 25 re¯ections = 30 33 " = 0.64 mm 1 T = 293 (2) K Prism, colourless 0.43 á 0.40 á 0.36 mm

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

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Dmitry V. Albov et al.



C10H13NO

DOI: 10.1107/S1600536804010025

Acta Cryst. (2004). E60, o922ąo923


organic papers
Data collection
Enraf Nonius CAD-4 diffractometer Non-proŽled 3 scans Absorption correction: none 1740 measured re¯ections 1740 independent re¯ections 1183 re¯ections with I > 2' (I) max = 74.9 h = 12 3 10 k=038 l = 0 3 16 1 standard re¯ection every 200 re¯ections intensity decay: 2% H-atom parameters constrained w = 1/[' 2(Fo2) + (0.0733P)2] where P = (Fo2 + 2Fc2)/3 (ā/' )max < 0.001 é ā&max = 0.18 e A 3 é ā&min = 0.16 e A 3

ReŽnement
ReŽnement on F 2 R[F 2 > 2' (F 2)] = 0.045 wR(F 2) = 0.103 S = 0.87 1740 re¯ections 111 parameters

Table 1
N1īC9 N1īC2 N1īC11 C2īO2 C2īC3 C3īC4 C4īC5

Figure 1
1.3666 (16) 1.4027 (18) 1.4574 (17) 1.2469 (16) 1.427 (2) 1.3568 (19) 1.4232 (18) 120.81 120.91 118.28 119.67 124.94 115.38 123.92 117.55 122.49 119.93 (10) (12) (11) (13) (14) (11) (13) (12) (13) (12) C4īC10 C5īC9 C5īC6 C6īC7 C7īC8 C8īC9 C9īC5īC4 C9īC5īC6 C4īC5īC6 C5īC6īC7 C8īC7īC6 C9īC8īC7 C5īC9īN1 C5īC9īC8 N1īC9īC8 1.4940 (19) 1.3490 (17) 1.5052 (18) 1.537 (2) 1.525 (2) 1.5044 (18) 119.64 111.04 129.21 103.41 107.84 102.93 122.57 112.87 124.55 (11) (12) (12) (11) (12) (11) (12) (11) (11)

é Selected geometric parameters (A, ).

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

(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 (Farrugia, 1999).

C9īN1īC2 C9īN1īC11 C2īN1īC11 O2īC2īN1 O2īC2īC3 N1īC2īC3 C4īC3īC2 C3īC4īC5 C3īC4īC10 C5īC4īC10

The authors are indebted to the Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database (project 02-07-90322).

References
Albov, D. V., Mazina, O. S., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004). Crystallogr. Rep. 49. In the press. Albov, D. V., Rybakov, V. B., Babaev, E. V., Fedyanin, I. V. & Aslanov, L. A. (2004). Acta Cryst. E60, o892 o893. 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.

In (2), H atoms were included in calculated positions and reŽned as riding atoms. Calculated C H bond lengths are in the range 0.93 é 0.97 A. For methyl H atoms, Uiso values were set equal to 1.5Ueq of the carrier atoms; for other H atoms, Uiso values were set to 1.2Ueq of the carrier atoms. 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

Acta Cryst. (2004). E60, o922ąo923

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C10H13NO

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