5-[(E)-Meth­oxy(phen­yl)methyl­idene]-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole

Maji, B.; Berionni, G.; Mayr, H.; Mayer, P.

doi:10.1107/S1600536812045692

Volume 68
Part 12
Page o3307
December 2012

Received 19 July 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.116
Data-to-parameter ratio = 13.1
Details

5-[(E)-Methoxy(phenyl)methylidene]-1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazole

Biplab Maji,^a Guillaume Berionni,^a Herbert Mayr ^a and Peter Mayer ^a ^*

^aLudwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany
Correspondence e-mail: pemay@cup.uni-muenchen.de

In the title compound, C₂₈H₂₃N₃O, the 1,2,4-triazole ring deviates slightly from planarity adopting a ^N3T_C2 conformation which is distorted towards an E_C2 conformation. The plane around the ethylene unit makes a dihedral angle of 17.32 (11)° with the mean plane [r.m.s. deviation = 0.036 (1) Å] of the 1,2,4-triazole fragment. The dihedral angles between the four phenyl rings and the 1,2,4-triazole ring are 31.01 (10), 49.01 (8), 78.55 (6) and 41.51 (9)°. In the crystal, molecules are linked along [100] by weak C-HO hydrogen bonds.

Related literature

For chemical background, see: Arduengo et al. (1991); Enders et al. (2007); Biju et al. (2011); Breslow (1958). For puckering analysis, see: Cremer & Pople (1975). For a related structure, see: Nair et al. (2008).

Experimental

Crystal data

C₂₈H₂₃N₃O
M_r = 417.49
Monoclinic, P 2₁ /c
a = 5.8831 (2) Å
b = 10.5560 (2) Å
c = 35.0548 (8) Å
= 93.749 (1)°
V = 2172.31 (10) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 200 K
0.35 × 0.09 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
12170 measured reflections
3797 independent reflections
2601 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.116
S = 1.02
3797 reflections
290 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C20-H20O1ⁱ	0.95	2.43	3.162 (3)	134
Symmetry code: (i) x-1, y, z.

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2259 ).

Acknowledgements

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

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.
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.
Biju, A. T., Kuhl, N. & Glorius, F. (2011). Acc. Chem. Res. 44, 1182-1195.
Breslow, R. (1958). J. Am. Chem. Soc. 80, 3719-3726.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Enders, D., Niemeier, O. & Henseler, A. (2007). Chem. Rev. 107, 5606-5655.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nair, V., Mathew, S. C., Vallalath, S., Pillai, A. N. & Suresh, E. (2008). Synthesis, pp. 551-554.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds