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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

1-(4-Chlorophenacyl)-4-methyl-6,7,8,9tetrahydro-5H-cyclohepta[b]pyridin2(1H)-one
In the pyridone ring of the title compound, C19H20ClNO2, single and double bonds alternate, though allowing some degree of conjugation. One C atom in the cycloheptene ring is disordered over two positions, which form boat and chair conformations of cycloheptene, respectively.
Received 15 April 2004 Accepted 21 April 2004 Online 30 April 2004

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

Comment
In the course of our systematic study of the size effect of cycloalkane fragments on the reactivity of pyridine-based heterocycles (Albov, Rybakov, Babaev & Aslanov, 2004), we have described earlier the crystal structure of 2-methoxy-4methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine, (1) (Albov, Rybakov, Babaev, Fedyanin & Aslanov, 2004). We report here the crystal structure of the title compound, (2) (Fig. 1).

Key indicators Single-crystal X-ray study T = 293 K é Mean ' (CąC) = 0.002 A Disorder in main residue R factor = 0.041 wR factor = 0.106 Data-to-parameter ratio = 14.5 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

In the pyridone ring (N1/C11) of (2), the single and double bonds alternate (Table 1), though allowing some degree of conjugation. Atoms C7 and C9 are displaced from the plane of é the pyridone ring by 1.412 (4) and 1.322 (3) A, respectively. Atom C8 of the cycloheptene ring is disordered over two sites, with occupancies of 0.69 (1) and 0.31 (1), forming the boat and chair conformations of cycloheptene, respectively. The torsion angle C20 C15 C14 O14 is 24.4 (2) and the dihedral angle between the benzene and pyridone rings is 49.88 (6) .

Experimental
Compound (1) (2.50 g) and 4 chlorophenacyl bromide (3.06 g) were boiled in acetonitrile for 6 h. When thin layer chromatography showed only traces of the source compounds in the solution, the solvent was evaporated and the product was washed with acetone (yield 2.51 g, 58%). The product was recrystallized from acetone
DOI: 10.1107/S1600536804009730 Acta Cryst. (2004). E60, o894ąo895

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

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Dmitry V. Albov et al.



C19H20ClNO2


organic papers
(m.p. 481 483 K). 1H NMR (DMSO d6, 400 MHz, p.p.m.): 1.55 (m, 4H, 7 CH2 + 8 CH2), 1.78 (m, 2H, 9 CH2), 2.65 (m, 4H, 6 CH2 + 10 CH2), 5.66 (s, 2H, 13 CH2), 6.10 (s, 1H, 3 CH), 7.56, 8.08 (dd, 4 H, Ar). Crystal data
C19H20ClNO2 Mr = 329.81 Triclinic, P1 é a = 7.9540 (7) A é b = 8.6902 (7) A é c = 12.4984 (8) A = 108.342 (6) = 94.660 (6) = 96.760 (7) é V = 807.88 (11) A3 Z=2 Dx = 1.356 Mg m 3 Cu K radiation Cell parameters from 25 re¯ections = 30 35 " = 2.16 mm 1 T = 293 (2) K Prism, colourless 0.30 á 0.30 á 0.30 mm max = 74.7 h= 939 k = 10 3 10 l = 0 3 15 1 standard re¯ection every 200 re¯ections intensity decay: 1%

Data collection
Enraf Nonius CAD-4 diffractometer Non-proŽled 3 scans Absorption correction: none 3173 measured re¯ections 3173 independent re¯ections 2843 re¯ections with I > 2' (I)

ReŽnement
ReŽnement on F R[F 2 > 2' (F 2)] = 0.041 wR(F 2) = 0.106 S = 1.06 3173 re¯ections 219 parameters H-atom parameters constrained
2

Figure 1
w = 1/[' (Fo ) + (0.0448P) + 0.3555P] where P = (Fo2 + 2Fc2)/3 (ā/' )max = 0.001 é ā&max = 0.17 e A 3 é ā&min = 0.20 e A 3
2 2 2

ORTEP 3 (Farrugia, 1997) view of (2), with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of disordered atom C8, namely C8A, is shown.

Table 1

é Selected geometric parameters (A, ).
Cl1īC18 N1īC11 N1īC2 N1īC13 C2īO2 C2īC3 C3īC4 C4īC5 C4īC12 C5īC11 C5īC6 C11īN1īC2 C11īN1īC13 C2īN1īC13 O2īC2īN1 O2īC2īC3 N1īC2īC3 C4īC3īC2 C3īC4īC5 C3īC4īC12 C5īC4īC12 C11īC5īC4 1.7414 (16) 1.3747 (19) 1.399 (2) 1.4641 (17) 1.241 (2) 1.431 (2) 1.357 (2) 1.426 (2) 1.509 (2) 1.3730 (19) 1.507 (2) 122.99 121.37 115.56 120.49 124.82 114.69 123.28 119.42 119.76 120.82 118.58 (12) (12) (13) (14) (15) (14) (15) (13) (16) (16) (14) C6īC7 C7īC8B C7īC8A C8AīC9 C8BīC9 C9īC10 C10īC11 C13īC14 C14īO14 C14īC15 C11īC5īC6 C4īC5īC6 C8BīC9īC10 C5īC11īN1 C5īC11īC10 N1īC11īC10 N1īC13īC14 O14īC14īC15 O14īC14īC13 C15īC14īC13 1.538 (3) 1.485 (9) 1.511 (5) 1.434 (4) 1.461 (8) 1.542 (3) 1.509 (2) 1.5150 (19) 1.2122 (18) 1.490 (2) 118.81 (15) 122.58 (14) 120.8 (3) 120.98 (13) 119.17 (14) 119.85 (13) 111.69 (12) 121.28 (13) 120.76 (13) 117.95 (12)

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 (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).

References
Albov, D. V., 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 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.

All H atoms were positioned geometrically and reŽned as riding é (C H 0.93 0.97 A), with Uiso(H) 1.2 or 1.5Ueq(C).

Acta Cryst. (2004). E60, o894ąo895

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