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)

Herget, K.; Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536813003498

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 (C-C) = 0.012 Å
Disorder in main residue
R = 0.061
wR = 0.153
Data-to-parameter ratio = 15.7
Details

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)

Karoline Herget,^a Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^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); Huisgen et al. (1961); Glang et al. (2008). For structures of tetrazoles, see: Rieth et al. (2011). For structures of related tristriazolotriazines, see: Christiano et al. (2008). For liquid-crystalline tristriazolotriazines, see: Christiano et al. (2008, 2012); Glang et al. (2013). For isomeric tristriazolotriazines, see: Tartakovsky et al. (2005); Borchmann et al. (2010). For star-shaped conjugated oligomers, see: Schmitt et al. (2011); Detert et al. (2010).

Experimental

Crystal data

C₅₄H₆₉N₉O₃·CHCl₃·C₂H₆O
M_r = 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 radiation
= 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(I)
R_int = 0.168

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.153
S = 0.78
10791 reflections
687 parameters
26 restraints
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 4585 Friedel pairs
Flack parameter: 0.03 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2L-H2LN12ⁱ	0.84	2.11	2.896 (10)	156
Symmetry code: (i) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2011); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2011); 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: NC2304 ).

Acknowledgements

The authors are grateful to Heinz Kolshorn for helpful discussions.

References

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