[Journal logo]

Volume 69 
Part 3 
Page o380  
March 2013  

Received 24 January 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.168
Data-to-parameter ratio = 19.8
Details
Open access

4-(1H-Tetrazol-5-yl)benzene-1,3-diol

aDepartment of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Republic of Korea
Correspondence e-mail: ykim@chungbuk.ac.kr

In the title compound, C7H6N4O2, rings are almost coplanar, the dihedral angle between them being 8.45 (13)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, the molecules are linked by O-H...N and N-H...O hydrogen bonds into a three-dimensional network.

Related literature

For the structure of 4-(5-tetrazolyl)-1,3-benzenediol sesquihydrate, see: Gallardo et al. (1995[Gallardo, H., Meyer, E. & Vencato, I. (1995). Acta Cryst. C51, 2430-2432.]). For the synthesis, see: Meyer et al. (1998[Meyer, E., Zucco, C. & Gallardo, H. (1998). J. Mater. Chem., 8, 1351-1354.]).

[Scheme 1]

Experimental

Crystal data
  • C7H6N4O2

  • Mr = 178.16

  • Orthorhombic, P c c n

  • a = 16.109 (2) Å

  • b = 7.2931 (11) Å

  • c = 12.8708 (17) Å

  • V = 1512.2 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.10 × 0.10 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.96, Tmax = 0.98

  • 20096 measured reflections

  • 2452 independent reflections

  • 1273 reflections with I > 2[sigma](I)

  • Rint = 0.110

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.168

  • S = 1.05

  • 2452 reflections

  • 124 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N4i 0.82 1.94 2.759 (3) 173
O2-H2...N3ii 0.82 2.00 2.817 (3) 173
N1-H101...O1 0.89 (3) 2.22 (3) 2.701 (3) 113 (2)
N1-H101...O2iii 0.89 (3) 2.40 (3) 3.034 (3) 129 (2)
C3-H3...N2ii 0.93 2.57 3.439 (3) 155
Symmetry codes: (i) [-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+2]; (iii) [x+{\script{1\over 2}}, -y+2, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2096 ).


Acknowledgements

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MEST) (No. 2010-0007092).

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gallardo, H., Meyer, E. & Vencato, I. (1995). Acta Cryst. C51, 2430-2432.  [CrossRef] [details]
Meyer, E., Zucco, C. & Gallardo, H. (1998). J. Mater. Chem., 8, 1351-1354.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o380  [ doi:10.1107/S160053681300411X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.