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organic papers
Acta Crystallographica Section E

Structure Reports Online
ISSN 1600-5368

4-Methyl-1-(3-nitrophenacyl)-5,6,7,8-tetrahydroquinolin-2(1H)-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@struct.chem.msu.ru

In the pyridone ring of the title compound, C18H18N2O4, single and double bonds alternate, showing some degree of conjugation.

Received 24 September 2004 Accepted 29 September 2004 Online 9 October 2004

Comment
In the course of our systematic study of the effect of the size of cycloalkane fragments on the reactivity of pyridine-based heterocycles, we have previously described the crystal structure of 2-methoxy-4-methyl-5,6,7,8-tetrahydroquinoline, (1) (Albov et al., 2004a). We report here the crystal structure of 4methyl-1-(3-nitrophenacyl)-5,6,7,8-tetrahydroquinolin-2(1H)one, (2) (Fig. 1).

Key indicators Single-crystal X-ray study T = 293 K é Mean ' (CąC) = 0.003 A R factor = 0.049 wR factor = 0.129 Data-to-parameter ratio = 14.2 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 C10 of (2), the single and double bonds alternate, showing some degree of delocalization. Atoms C6, C7 and C8 are displaced from this plane by é ū0.144 (4), 0.258 (4) and 0.332 (5) A, respectively. Atoms C12, C13, O13, N2 and O21 lie in the plane of the benzene é ring; only atom O22 is displaced from the plane by 0.136 (3) A, and the torsion angle O13 C13 C14 C15 is 0.0 (2) . It is evident that the 3-nitrobenzoyl fragment is completely conjugated. The dihedral angle between the benzene and pyridone rings is 85.45 (6) . These angles are almost the same as in the 4-chlorophenacyl relative, but do not agree with cycloheptene and cyclooctene derivatives (Albov et al., 2004b,c).

Experimental
Compound (1) (4.00 g) and 3 nitrophenacyl bromide (4.10 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 washed with acetone (yield 3.83 g, 52%). The product was recrystallized from acetone (m.p. 441 443 K). 1H NMR (DMSO d6, 400 MHz, p.p.m.): 1.73 (m, 4H, 7 CH2 + 8 CH2), 2.12 (s, 3H, 11 CH3), 2.48 (m, 4H, 6 CH2 + 9 CH2), 5.56 (s, 2H, 12 CH2), 6.13 (s, 1H, 3 CH), 7.84 (t, 1H, 16 CH), 8.49 (m, 2H, 15 CH + 17 CH), 8.80 (s, 1H, 19 CH).
doi: 10.1107/S1600536804024468 Acta Cryst. (2004). E60, o1952ąo1953

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

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Dmitry V. Albov et al.



C18H18N2O4


organic papers
Crystal data
C18H18N2O4 Mr = 326.34 Triclinic, P1 é a = 9.115 (3) A é b = 9.271 (3) A é c = 11.248 (3) A = 92.00 (2) = 105.09 (2) = 118.82 (2) é V = 789.5 (5) A3 Z=2 Dx = 1.373 Mg m 3 Mo K radiation Cell parameters from 25 re¯ections = 12 14 " = 0.10 mm 1 T = 293 (2) K Prism, light yellow 0.25 á 0.24 á 0.22 mm max = 26.0 h = 11 3 10 k = 11 3 11 l = 0 3 13 1 standard re¯ection every 200 re¯ections intensity decay: 8% H-atom parameters constrained w = 1/[' 2(Fo2) + (0.0704P)2] where P = (Fo2 + 2Fc2)/3 (ā/' )max < 0.001 é ā&max = 0.13 e A 3 é ā&min = 0.15 e A 3

Data collection
Enraf Nonius CAD-4 diffractometer Non-proŽled 3 scans Absorption correction: none 3103 measured re¯ections 3103 independent re¯ections 1936 re¯ections with I > 2' (I)

Refinement
ReŽnement on F 2 R[F 2 > 2' (F 2)] = 0.050 wR(F 2) = 0.129 S = 1.06 3103 re¯ections 218 parameters

Table 1
N1īC2 N1īC10 N1īC12 C2īO2 C2īC3 C3īC4 C4īC5 C4īC11 C5īC10 C5īC6 C6īC7

é Selected geometric parameters (A, ).
1.391 1.399 1.450 1.225 1.414 1.356 1.434 1.495 1.351 1.517 1.531 (3) (2) (2) (3) (2) (3) (3) (3) (3) (3) (4) C7īC8 C8īC9 C9īC10 C12īC13 C13īO13 C13īC14 C18īN2 N2īO22 N2īO21 1.526 1.493 1.533 1.509 1.210 1.475 1.454 1.202 1.233 (4) (4) (3) (3) (3) (2) (3) (2) (2)

Figure 1

ORTEP 3 view (Farrugia, 1997) of (2) with the atom numbering scheme. Atomic 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).

C2īN1īC10 C2īN1īC12 C10īN1īC12 O2īC2īN1 O2īC2īC3 N1īC2īC3 C4īC3īC2 C3īC4īC5 C3īC4īC11 C5īC4īC11 C10īC5īC4 C10īC5īC6 C4īC5īC6 C5īC6īC7 C8īC7īC6

123.62 (14) 115.07 (15) 121.23 (16) 121.02 (16) 125.00 (18) 113.90 (16) 123.90 (18) 119.34 (17) 120.02 (19) 120.63 (19) 118.61 (17) 123.68 (19) 117.71 (17) 113.9 (2) 118.4 (2)

C9īC8īC7 C8īC9īC10 C5īC10īN1 C5īC10īC9 N1īC10īC9 N1īC12īC13 O13īC13īC14 O13īC13īC12 C14īC13īC12 C17īC18īN2 C19īC18īN2 O22īN2īO21 O22īN2īC18 O21īN2īC18

122.5 (2) 112.8 (2) 120.12 (17) 124.37 (18) 115.50 (16) 114.26 (15) 121.47 (15) 120.32 (16) 118.21 (14) 118.21 (15) 119.15 (15) 121.65 (18) 120.14 (18) 118.20 (14)

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).

References
Albov, D. V., Rybakov, V. B., Babaev, E. V. & Aslanov, L. A. (2004a). Crystallogr. Rep. 49, 430 436. 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, o1219 o1221. 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.

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). The methyl group was allowed to rotate but not to tip. 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, o1952ąo1953

Dmitry V. Albov et al.



C18H18N2O4

o1953