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Volume 69 
Part 3 
Pages o365-o366  
March 2013  

Received 28 January 2013
Accepted 4 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.012 Å
Disorder in main residue
R = 0.061
wR = 0.153
Data-to-parameter ratio = 15.7
Details
Open access

3,7,11-Tris{4-[(1R,3S,4S)-neomenthyloxy]phenyl}tri[1,2,4]triazolo[4,3-a:4',3'-c:4'',3''-e][1,3,5]triazine-chloroform-ethanol (1/1/1)

aUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: detert@uni-mainz.de

The title compound, C54H69N9O3·CHCl3·C2H5OH, was prepared by a threefold nucleophilic substitution of p-neomenthyloxyphenyltetrazole on cyanuric chloride followed by threefold cycloelimination of nitrogen and ring closure. The central tristriazolotriazine is roughly planar with a maximum deviation of 0.089 (7) Å but the adjacent benzene rings are twisted out of this plane. N-C-C-C torsion angles of -80.2 (9), 159.3 (7) and 50.6 (10)° destroy the formal C3 symmetry. Cavities are found between the phenoxy residues: one is occupied by a chloroform molecule, another by ethanol forming a hydrogen bond to a triazole ring while two isopropyl groups point into the third void. One methyl group and the chlorofrm molecule are disorderd and were refined using a split model.

Related literature

For the synthesis of related tristriazolotriazines, see: Hofmann & Erhardt (1912[Hofmann, K. A. & Erhardt, O. (1912). Chem. Ber. 45, 2731-2740.]); Huisgen et al. (1961[Huisgen, R., Sturm, H. J. & Seidel, M. (1961). Chem. Ber. 94, 1555-1562.]); Glang et al. (2008[Glang, S., Schmitt, V. & Detert, H. (2008). Proceedings of the 36th German Topical Meeting on Liquid Crystals, pp. 125-128.]). For structures of tetrazoles, see: Rieth et al. (2011[Rieth, T., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o156.]). For structures of related tristriazolotriazines, see: Christiano et al. (2008[Christiano, R., Gallardo, H., Bortoluzzi, A. J., Bechtold, I. H., Campos, C. E. M. & Longo, L. R. (2008). Chem. Commun. pp. 5134-5136.]). For liquid-crystalline tristriazolotriazines, see: Christiano et al. (2008[Christiano, R., Gallardo, H., Bortoluzzi, A. J., Bechtold, I. H., Campos, C. E. M. & Longo, L. R. (2008). Chem. Commun. pp. 5134-5136.], 2012[Christiano, R., Eccher, J., Bechtold, I. H., Tironi, C. N., Vieira, A. A., Molin, F. & Gallardo, H. (2012). Langmuir, 28, 11590-11598.]); Glang et al. (2013[Glang, S., Borchmann, D., Rieth, T. & Detert, H. (2013). Adv. Sci. Technol. 77, 118-123.]). For isomeric tristriazolotriazines, see: Tartakovsky et al. (2005[Tartakovsky, V. A., Frumkin, A. E., Churakov, A. M. & Strelenko, Y. A. (2005). Russ. Chem. Bull. 54, 719-725.]); Borchmann et al. (2010[Borchmann, D., Kratochwil, M., Glang, S. & Detert, H. (2010). Proceedings of the 38th GermanTopical Meeting on Liquid Crystals, pp. 133-138.]). For star-shaped conjugated oligomers, see: Schmitt et al. (2011[Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o1553.]); Detert et al. (2010[Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218-3330.]).

[Scheme 1]

Experimental

Crystal data
  • C54H69N9O3·CHCl3·C2H6O

  • Mr = 1057.62

  • Orthorhombic, P 21 21 21

  • a = 6.6562 (5) Å

  • b = 14.1000 (14) Å

  • c = 60.756 (5) Å

  • V = 5702.1 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 193 K

  • 0.5 × 0.06 × 0.02 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • 32105 measured reflections

  • 10791 independent reflections

  • 2815 reflections with I > 2[sigma](I)

  • Rint = 0.168

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.153

  • S = 0.78

  • 10791 reflections

  • 687 parameters

  • 26 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4585 Friedel pairs

  • Flack parameter: 0.03 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2L-H2L...N12i 0.84 2.11 2.896 (10) 156
Symmetry code: (i) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2011[Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2011[Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2304 ).


Acknowledgements

The authors are grateful to Heinz Kolshorn for helpful discussions.

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]
Borchmann, D., Kratochwil, M., Glang, S. & Detert, H. (2010). Proceedings of the 38th GermanTopical Meeting on Liquid Crystals, pp. 133-138.
Christiano, R., Eccher, J., Bechtold, I. H., Tironi, C. N., Vieira, A. A., Molin, F. & Gallardo, H. (2012). Langmuir, 28, 11590-11598.  [ISI] [PubMed]
Christiano, R., Gallardo, H., Bortoluzzi, A. J., Bechtold, I. H., Campos, C. E. M. & Longo, L. R. (2008). Chem. Commun. pp. 5134-5136.
Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218-3330.  [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Glang, S., Borchmann, D., Rieth, T. & Detert, H. (2013). Adv. Sci. Technol. 77, 118-123.  [CrossRef]
Glang, S., Schmitt, V. & Detert, H. (2008). Proceedings of the 36th German Topical Meeting on Liquid Crystals, pp. 125-128.
Hofmann, K. A. & Erhardt, O. (1912). Chem. Ber. 45, 2731-2740.
Huisgen, R., Sturm, H. J. & Seidel, M. (1961). Chem. Ber. 94, 1555-1562.  [CrossRef] [ChemPort]
Rieth, T., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o156.  [CrossRef] [details]
Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o1553.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany.
Tartakovsky, V. A., Frumkin, A. E., Churakov, A. M. & Strelenko, Y. A. (2005). Russ. Chem. Bull. 54, 719-725.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o365-o366   [ doi:10.1107/S1600536813003498 ]

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