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Volume 69 
Part 11 
Page o1605  
November 2013  

Received 23 September 2013
Accepted 29 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.074
Data-to-parameter ratio = 12.6
Details
Open access

1H-Benzotriazole-4-hy­droxy­benzoic acid (1/1)

aDepartment of Physics, Presidency College, Chennai 600 005, India,bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India,cDepartment of Physics, Presidency College, Chennai 600 005, India, and dKunthavai Naacchiyaar Govt. Arts College (W), Thanjavur 613 007, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, kan_uma6@yahoo.com

The asymmetric unit of the title compound, C6H5N3·C7H6O3, comprises independent benzotriazole and 4-hydroxybenzoic acid molecules. The dihedral angle between the benzene ring and the benzotriazole ring system is 15.18 (7)°. The mean plane of the carb­oxyl group is twisted at an angle of 18.55 (1)° with respect to the benzene ring. The crystal structure is stabilized by weak inter­molecular N-H...N, O-H...N, O-H...O and C-H...O inter­actions, forming a three-dimensional network.

Related literature

For biological activities of benzotriazole derivates, see: Dubey et al. (2011[Dubey, A., Srivastava, S. K. & Srivastava, S. D. (2011). Bioorg. Med. Chem. Lett. 21, 569-573.]); Gaikwad, et al. (2012[Gaikwad, N. D., Patil, S. V. & Bodade, V. D. (2012). Bioorg. Med. Chem. Lett. 22, 3449-3454.]). For reported structures, see: Sieron (2007[Sieron, L. (2007). Acta Cryst. E63, o2089-o2090.]); Sudhahar et al.(2013[Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.]); Yang et al. (2010[Yang, Y. X., Li, K., Wang, Y. J. & Li, Q. (2010). Beijing Shifan Dax. Xue. Zir. Kex. (J. B. Norm. Univ.), 46, 160-165.]).

[Scheme 1]

Experimental

Crystal data
  • C6H5N3·C7H6O3

  • Mr = 257.25

  • Orthorhombic, P n a 21

  • a = 17.3634 (13) Å

  • b = 11.4669 (9) Å

  • c = 6.0818 (4) Å

  • V = 1210.91 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.30 × 0.26 × 0.24 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.970, Tmax = 0.976

  • 6611 measured reflections

  • 2195 independent reflections

  • 1925 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.074

  • S = 1.04

  • 2195 reflections

  • 174 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.20 2.982 (2) 152
O2-H2A...N3ii 0.82 1.87 2.6817 (19) 169
O3-H3A...O1iii 0.82 1.88 2.6912 (17) 171
C13-H13...O3iv 0.93 2.49 3.373 (2) 159
Symmetry codes: (i) [-x, -y+2, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+1]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2200 ).


Acknowledgements

The authors thanks SAIF, IIT, Madras, for data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dubey, A., Srivastava, S. K. & Srivastava, S. D. (2011). Bioorg. Med. Chem. Lett. 21, 569-573.  [CrossRef] [ChemPort] [PubMed]
Gaikwad, N. D., Patil, S. V. & Bodade, V. D. (2012). Bioorg. Med. Chem. Lett. 22, 3449-3454.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sieron, L. (2007). Acta Cryst. E63, o2089-o2090.  [CSD] [CrossRef] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.  [CSD] [CrossRef] [IUCr Journals]
Yang, Y. X., Li, K., Wang, Y. J. & Li, Q. (2010). Beijing Shifan Dax. Xue. Zir. Kex. (J. B. Norm. Univ.), 46, 160-165.  [ChemPort]


Acta Cryst (2013). E69, o1605  [ doi:10.1107/S1600536813026767 ]

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