2-Methyl-4-phenyl-3,4-dihydro­quinazoline

Valkonen, A.; Kolehmainen, E.; Zakrzewska, A.; Skotnicka, A.; Gawinecki, R.

doi:10.1107/S1600536811009664

Volume 67
Part 4
Pages o923-o924
April 2011

Received 9 March 2011
Accepted 14 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.004 Å
R = 0.046
wR = 0.095
Data-to-parameter ratio = 9.5
Details

2-Methyl-4-phenyl-3,4-dihydroquinazoline

Arto Valkonen,^a ^* Erkki Kolehmainen,^a Anna Zakrzewska,^b Agnieszka Skotnicka ^b and Ryszard Gawinecki ^b

^aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FIN-40014 Jyväskylä, Finland, and ^bUniversity of Technology and Life Sciences, Department of Chemistry, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland
Correspondence e-mail: arto.m.valkonen@jyu.fi

The title compound, C₁₅H₁₄N₂, was formed during the lithiation of 2-methylquinazoline with phenyllithium followed by hydrolysis of the intermediate lithium 2-methyl-4-phenyl-4H-quinazolin-3-ide. NMR spectra as well as single-crystal X-ray structural data indicate that the reaction product to have the same structure in chloroform solution as in the crystalline state. The phenyl substituent is twisted out of the plane of the 3,4-dihydroquinazoline ring system by 86.47 (7)°. In the crystal, intermolecular N-HN interactions connect the molecules into infinite chains.

Related literature

For organolithium compounds and lithiation, see: Gawinecki et al. (2006); Kolehmainen et al. (2000); Wakefield (1976); Armarego (1967). For previous characterizations of the title compound, see: Suri et al. (1993). For related structures, see: Rajnikant et al. (2002).

Experimental

Crystal data

C₁₅H₁₄N₂
M_r = 222.28
Trigonal, P 3₁
a = 9.5600 (4) Å
c = 11.2569 (5) Å
V = 890.97 (7) Å³
Z = 3
Mo K radiation
= 0.07 mm^-1
T = 123 K
0.35 × 0.13 × 0.12 mm

Data collection

Bruker-Nonius KappaCCD with APEXII detector diffractometer
6729 measured reflections
1468 independent reflections
1215 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.095
S = 1.06
1468 reflections
155 parameters
1 restraint
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3N1ⁱ	0.88	2.04	2.908 (3)	169
Symmetry code: (i) $[-y, x-y+1, z+{\script{1\over 3}}]$ .

Data collection: COLLECT (Bruker, 2008); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae, et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2274 ).

Acknowledgements

Academy Professor Kari Rissanen and the Academy of Finland (project No. 212588 for KR) are gratefully acknowledged for funding. Dr Katri Laihia is thanked for characterization of the NMR spectra.

References

Armarego, W. L. F. (1967). The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part I, Quinazolines, edited by D. J. Brown, p. 35. New York: Interscience.
Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA..
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gawinecki, R., Kolehmainen, E., Loghmani-Khouzani, H., Osmialowski, B., Lovász, T. & Rosa, P. (2006). Eur. J. Org. Chem. pp. 2817-2824.
Kolehmainen, E., Osmialowski, B., Krygowski, T. M., Kauppinen, R., Nissinen, M. & Gawinecki, R. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 1259-1266.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rajnikant, Gupta, V. K., Suri, O. P. & Lal, M. (2002). Indian J. Pure Appl. Phys. 40, 59-61.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suri, K. A., Satti, N. K., Mahajan, B., Suri, O. P. & Dhar, K. L. (1993). Indian J. Chem. Sect. B, 32, 1171-1172.
Wakefield, B. J. (1976). The Chemistry of Organolithium Compounds, pp. 26, 32, 112, 138, 190. Oxford: Pergamon Press.

organic compounds