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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 [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.116
Data-to-parameter ratio = 13.1
Details
Open access

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

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 N3TC2 conformation which is distorted towards an EC2 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-H...O hydrogen bonds.

Related literature

For chemical background, see: Arduengo et al. (1991[Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.]); Enders et al. (2007[Enders, D., Niemeier, O. & Henseler, A. (2007). Chem. Rev. 107, 5606-5655.]); Biju et al. (2011[Biju, A. T., Kuhl, N. & Glorius, F. (2011). Acc. Chem. Res. 44, 1182-1195.]); Breslow (1958[Breslow, R. (1958). J. Am. Chem. Soc. 80, 3719-3726.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Nair et al. (2008[Nair, V., Mathew, S. C., Vallalath, S., Pillai, A. N. & Suresh, E. (2008). Synthesis, pp. 551-554.]).

[Scheme 1]

Experimental

Crystal data
  • C28H23N3O

  • Mr = 417.49

  • Monoclinic, P 21 /c

  • a = 5.8831 (2) Å

  • b = 10.5560 (2) Å

  • c = 35.0548 (8) Å

  • [beta] = 93.749 (1)°

  • V = 2172.31 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.116

  • S = 1.02

  • 3797 reflections

  • 290 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O1i 0.95 2.43 3.162 (3) 134
Symmetry code: (i) x-1, y, z.

Data collection: COLLECT (Nonius, 1998)[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]; cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.  [CrossRef] [ChemPort] [ISI]
Biju, A. T., Kuhl, N. & Glorius, F. (2011). Acc. Chem. Res. 44, 1182-1195.  [ISI] [CrossRef] [ChemPort] [PubMed]
Breslow, R. (1958). J. Am. Chem. Soc. 80, 3719-3726.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Enders, D., Niemeier, O. & Henseler, A. (2007). Chem. Rev. 107, 5606-5655.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Nair, V., Mathew, S. C., Vallalath, S., Pillai, A. N. & Suresh, E. (2008). Synthesis, pp. 551-554.  [ISI] [CSD] [CrossRef]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3307  [ doi:10.1107/S1600536812045692 ]

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