5-Methyl-3-(3-methyl­phen­yl)-7-phenyl-1,2,4-triazolo[4,3-c]pyrimidine

Preis, J.; Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536811010683

Volume 67
Part 4
Page o987
April 2011

Received 21 March 2011
Accepted 22 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 13.9
Details

5-Methyl-3-(3-methylphenyl)-7-phenyl-1,2,4-triazolo[4,3-c]pyrimidine

Jasmin Preis,^a Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: detert@uni-mainz.de

The title compound, C₁₉H₁₆N₄, is one of the few known 3,7-diaryl-1,2,4-triazolo[4,3-c]pyrimidines. The triazolopyrimidine unit is essentially planar (r.m.s. deviation = 0.048 Å). The phenyl ring and the heterocyclic core subtend a dihedral angle of only 15.09 (6)°, whereas the m-tolyl ring is twisted by 71.80 (6)° out of the plane of the triazole ring. Two C-HN hydrogen bonds and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.7045 (8) Å] stabilize the crystal packing.

Related literature

For the synthesis of higher conjugated and annulated heterocyclic [pi] -systems, see: Detert & Schollmeyer (1999); Sugiono & Detert (2001). The acylation of tetrazoles with chloroazines and thermal ring transformation leads to triazolo annulated azines, see: Huisgen, Sauer & Seidel (1960); Huisgen, Sturm & Markgraf (1960); Huisgen et al. (1961); Glang et al. (2008). Whereas a broad variety of triazolopyrimidines are known, only two further [1,2,4]triazolo[4,3-c]pyrimidines with a 3,7-diaryl substitution have been reported so far, see: Seada et al. (1992).

Experimental

Crystal data

C₁₉H₁₆N₄
M_r = 300.36
Triclinic, $[P \overline 1]$
a = 6.4270 (4) Å
b = 11.1706 (6) Å
c = 11.3672 (7) Å
= 79.963 (5)°
= 74.894 (5)°
= 81.877 (5)°
V = 771.88 (8) Å³
Z = 2
Cu K radiation
= 0.63 mm^-1
T = 193 K
0.45 × 0.40 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
3207 measured reflections
2924 independent reflections
2573 reflections with I > 2(I)
R_int = 0.088
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.03
2924 reflections
211 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6N8ⁱ	0.95	2.53	3.4597 (17)	166
C23-H23N8ⁱ	0.95	2.61	3.5374 (19)	167
Symmetry code: (i) -x, -y, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5497 ).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Detert, H. & Schollmeyer, D. (1999). Synthesis, pp. 999-1004.
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Glang, S., Schmitt, V. & Detert, H. (2008). Proc. 36th German Topical Meeting Liq. Cryst. Otto-von-Guericke Universität, Magdeburg,12-14 March , pp. 125-128.
Huisgen, R., Sauer, J. & Seidel, M. (1960). Chem. Ber. 93, 2885-2891.
Huisgen, R., Sturm, H. J. & Markgraf, J. H. (1960). Chem. Ber. 93, 2106-2124.
Huisgen, R., Sturm, H. J. & Seidel, M. (1961). Chem. Ber. 94, 1555-1562.
Seada, M., Abdel-Halim, A. M., Ibrahim, S. S. & Abdel-Megid, M. (1992). Asian J. Chem. 4, 544-552.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sugiono, E. & Detert, H. (2001). Synthesis, pp. 893-896.

organic compounds