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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

2-Methoxy-4-methyl-6,7,8,9-tetrahydro5H-cyclohepta[b]pyridine

Dmitry V. Albov,a* Victor B. Rybakov,a Eugene V. Babaev, Ivan V. Fedyaninb and Leonid A. Aslanova
a

a

The title compound, C12H17NO, was synthesized and characterized by 1H NMR and X-ray diffraction techniques.

Received 15 April 2004 Accepted 21 April 2004 Online 30 April 2004

Comment
In the course of systematic investigations of the size effect of cycloalkane fragments on the reactivity of corresponding heterocycles based on pyridine, we have described earlier the crystal structure of 4-methyl-1,5,6,7,8,9-hexahydro-2H-cyclohepta[b]pyridin-2-one, (1) (Albov, Mazina et al., 2004). According to the procedure of Albov, Rybakov et al. (2004), we have synthesized and characterized the title compound, (2).

Department of Chemistry, Moscow State University, 119992 Moscow, Russian Federation, and bInstitute of Organoelement Compounds, 117813 Moscow, Russian Federation Correspondence e-mail: albov@biocryst.phys.msu.su

Key indicators Single-crystal X-ray study T = 120 K é Mean ' (CąC) = 0.003 A R factor = 0.067 wR factor = 0.165 Data-to-parameter ratio = 12.6 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In (2), the pyridine ring (N1/C11) is planar within é 0.0072 (12) A. The attached atoms C6, C10, O2, C12 and C13 lie in that plane. Atoms C7, C8 and C9 are displaced from the é plane by 1.324 (5), 1.367 (5) and 1.324 (5) A, respectively. Bond lengths in the pyridine ring conŽrm its aromatic character. The cycloheptene ring is in a chair conformation (Fig. 1). The above results should be compared with the crystal structures of Žve- and eight-membered cycloalkane derivatives, which are in progress, as well as with published (Albov, Rybakov et al., 2004) six-membered cycloalkane derivatives.

Experimental
For the preparation of the title compound, (2), 4 methyl 1,5,6,7,8,9 hexahydro 2H cyclohepta[b]pyridin 2 one [(1); 7.69 g], methyl iodide (7.78 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 by rotary evaporation (yield: 3.14 g, 38%). The product was recrystallized from chloroform (m.p. 310 314 K). 1H NMR (DMSO d6, 400 MHz, p.p.m.): 1.55 (m, 2H, 8 CH2), 1.62 (m, 2H, 7 CH2), 1.84 (m, 2H, 9 CH2), 2.21 (s, 3H, 41 CH3), 2.67 (t, 2H, 6 CH2), 2.86 (t, 2H, 10 CH2), 3.77 (s, 3H, 21 CH3), 6.27 (s, 1H, 3 CH). Crystal data
C12H17NO Mr = 191.27 Monoclinic, P21 ac é a = 8.762 (2) A é b = 14.937 (4) A é c = 8.542 (7) A = 109.659 (6) é V = 1052.8 (9) A3 Z=4 Dx = 1.207 Mg m 3 Mo K radiation Cell parameters from 450 re¯ections = 3 26 " = 0.08 mm 1 T = 120 (2) K Needle, colourless 0.3 á 0.1 á 0.1 mm Acta Cryst. (2004). E60, o892ąo893

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

o892

Dmitry V. Albov et al.



C12H17NO

DOI: 10.1107/S1600536804009651


organic papers
Data collection
Bruker SMART 1000 CCD areadetector diffractometer 9 and 3 scans Absorption correction: multi-scan (SADABS; Sheldrick, 1998) Tmin = 0.991, Tmax = 0.992 7211 measured re¯ections 2498 independent re¯ections 1435 re¯ections with I > 2' (I) Rint = 0.007 max = 28.0 h = 10 3 11 k = 19 3 19 l = 9 3 11 H-atom parameters constrained w = 1/[' 2(Fo2) + (0.1049P)2] where P = (Fo2 + 2Fc2)/3 (ā/' )max < 0.001 é ā&max = 0.43 e A 3 é ā&min = 0.25 e A 3

ReŽnement
ReŽnement on F 2 R[F 2 > 2' (F 2)] = 0.067 wR(F 2) = 0.165 S = 0.90 2498 re¯ections 129 parameters

Figure 1

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

Table 1
N1īC2 N1īC11 O2īC2 O2īC13 C2īC3 C3īC4 C4īC5 C4īC12

é Selected geometric parameters (A, ).
1.325 1.358 1.359 1.428 1.383 1.381 1.412 1.495 117.40 116.29 118.95 123.75 117.31 119.32 118.05 119.29 122.65 118.35 (2) (2) (2) (3) (3) (3) (3) (3) C5īC11 C5īC6 C6īC7 C7īC8 C8īC9 C9īC10 C10īC11 C11īC5īC6 C4īC5īC6 C5īC6īC7 C8īC7īC6 C9īC8īC7 C8īC9īC10 C11īC10īC9 N1īC11īC5 N1īC11īC10 C5īC11īC10 1.383 1.512 1.548 1.520 1.513 1.537 1.498 119.94 121.70 114.66 114.11 115.69 114.26 114.20 123.11 114.34 122.52 (3) (3) (3) (3) (3) (3) (2)

Data collection: SMART (Bruker, 1998); cell reŽnement: SAINT Plus (Bruker, 1998); data reduction: SAINT Plus; 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 (Farrugia, 1999).

C2īN1īC11 C2īO2īC13 N1īC2īO2 N1īC2īC3 O2īC2īC3 C4īC3īC2 C3īC4īC5 C3īC4īC12 C5īC4īC12 C11īC5īC4

(16) (16) (17) (17) (17) (17) (17) (18) (17) (17)

(17) (17) (16) (17) (17) (17) (16) (17) (16) (17)

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).

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. & Aslanov, L. A. (2004). Crystallogr. Rep. 49. In the press. Bruker (1998). SAINT-Plus (Version 6.01) and SMART (Version 5.059) Bruker AXS Inc., Madison, Wisconsin, USA. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837 838. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of õ Gottingen, Germany. Sheldrick G. M. (1998). SADABS. Version 2.01. Bruker AXS Inc., Madison, Wisconsin, USA.

H atoms were included in calculated positions and reŽned as riding é atoms, with C H lengths in the range 0.95 0.99 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.

Acta Cryst. (2004). E60, o892ąo893

Dmitry V. Albov et al.



C12H17NO

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