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Volume 68 
Part 12 
Page o3297  
December 2012  

Received 27 October 2012
Accepted 30 October 2012
Online 7 November 2012

[tk5165sup1]
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Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.052
wR = 0.140
Data-to-parameter ratio = 10.2
Details
Open access

1-Benzyl-1H-benzotriazole 3-oxide monohydrate

P. Selvarathy Grace,a Samuel Robinson Jebas,b B. Ravindran Durai Nayagama* and Dieter Schollmeyerc

aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India,bDepartment of Physics, Sethupathy Government Arts College, Ramanathapuram 623 502, Tamilnadu, India, and cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

In the title hydrate, C13H11N3O·H2O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methylene group, forming a dihedral angle of 81.87 (15)°. In the crystal, molecules are linked into chains along [001] by O-H...O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C-H...O, C-H...[pi] and [pi]-[pi] [centroid-centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] interactions.

Related literature

For the biological activity of benzotriazole derivatives, see: Kopanska et al. (2005[Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2005). Bioorg. Med. Chem. 13, 3601-3616.]); Sarala et al. (2007[Sarala, G., Swamy, S. N., Prabhuswamy, B., Andalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2007). Anal. Sci. 23, 25-26.]). For their applications, see: Kopec et al. (2008[Kopec, E. A., Zwolska, Z. & Kazimierczuk, A. O. Z. (2008). Acta Pol. Pharm. Drug Res. 65, 435-439.]); Krawczyk & Gdaniec (2005[Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967-o2969.]); Smith et al. (2001[Smith, G., Bottle, S. E., Reid, D. A., Schweinsberg, D. P. & Bott, R. C. (2001). Acta Cryst. E57, o531-o532.]); Sha et al. (1996[Sha, G., Wang, W. & Ren, T. (1996). Mocha Xuebao, 16, 344-350.]). For a related structure, see: Selvarathy Grace et al. (2012[Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11N3O·H2O

  • Mr = 243.26

  • Orthorhombic, P n a 21

  • a = 12.556 (5) Å

  • b = 20.881 (8) Å

  • c = 4.6651 (18) Å

  • V = 1223.1 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.40 × 0.05 × 0.04 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • 15911 measured reflections

  • 1677 independent reflections

  • 1118 reflections with I > 2[sigma](I)

  • Rint = 0.132
Refinement

  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.140

  • S = 0.98

  • 1677 reflections

  • 164 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11-C16 phenyl ring.
D-H...A D-H H...A D...A D-H...A
O1W-H1W...O1Wi 0.82 1.93 2.744 (3) 169
O1W-H2W...O17 0.85 1.95 2.800 (3) 180
C10-H10A...O17ii 0.99 2.45 3.400 (5) 161
C10-H10B...Cg3iii 0.99 2.51 3.382 (4) 147
Symmetry codes: (i) [-x+1, -y, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iii) x, y, z-1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: 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: TK5165 ).

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2005). Bioorg. Med. Chem. 13, 3601-3616.
Kopec, E. A., Zwolska, Z. & Kazimierczuk, A. O. Z. (2008). Acta Pol. Pharm. Drug Res. 65, 435-439.
Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967-o2969.  [CSD] [CrossRef] [details]
Sarala, G., Swamy, S. N., Prabhuswamy, B., Andalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2007). Anal. Sci. 23, 25-26.  [PubMed]
Selvarathy Grace, P., Jebas, S. R., Ravindran Durai Nayagam, B. & Schollmeyer, D. (2012). Acta Cryst. E68, o1132.  [CSD] [CrossRef] [details]
Sha, G., Wang, W. & Ren, T. (1996). Mocha Xuebao, 16, 344-350.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Bottle, S. E., Reid, D. A., Schweinsberg, D. P. & Bott, R. C. (2001). Acta Cryst. E57, o531-o532.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o3297  [ doi:10.1107/S1600536812044868 ]

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