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Volume 66 
Part 3 
Page o637  
March 2010  

Received 26 January 2010
Accepted 7 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 13.8
Details
Open access

1-Mesitylmethyl-1Hbenzotriazole 3-oxide

aDepartment of Chemistry, Popes College, Sawyerpuram 628251, Tamilnadu, India,bDepartment of Physics, Sethupathy Government Arts College, Ramanathapuram 623502, Tamilnadu, India,cDepartment of Chemistry, Sarah Tucker College, Tirunelveli 627007, Tamilnadu, India,dDepartment of Chemistry, T.D.M.N.S. College, T. Kallikulam, Tamilnadu, India, and eInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

In the title compound, C16H17N3O, the benzotriazole ring forms a dihedral angle of 77.25 (6)° with the phenyl ring. The benzotriazole ring is essentially planar with a maximum deviation of 0.012 (19) Å. Weak intermolecular C-H...O hydrogen bonds form R22(10) motifs. The crystal packing is consolidated by [pi]-[pi] interactions with centroid-centroid distances of 3.5994 (12) Å together with very weak C-H...[pi] interactions.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem.Soc. Perkin Trans. 2, pp. S1-S19.]). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17N3O

  • Mr = 267.33

  • Monoclinic, P 21 /c

  • a = 8.6269 (19) Å

  • b = 7.3422 (4) Å

  • c = 21.890 (5) Å

  • [beta] = 103.133 (11)°

  • V = 1350.2 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 193 K

  • 0.35 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (CORINC; Draeger & Gattow (1971[Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]) Tmin = 0.799, Tmax = 0.936

  • 2722 measured reflections

  • 2545 independent reflections

  • 2243 reflections with I > 2[sigma](I)

  • Rint = 0.091

  • 3 standard reflections every 60 min intensity decay: 2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.132

  • S = 1.09

  • 2546 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12-C17 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O10i 0.95 2.35 3.190 (2) 147
C16-H16...O10ii 0.95 2.58 3.506 (2) 165
C18-H18A...Cg3iii 0.98 2.98 3.810 (18) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971[Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and 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: BT5182 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem.Soc. Perkin Trans. 2, pp. S1-S19.  [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.  [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
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 (2010). E66, o637  [ doi:10.1107/S1600536810004824 ]

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