4-(1H-Tetra­zol-5-yl)benzene-1,3-diol

Kim, Y.

doi:10.1107/S160053681300411X

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.168
Data-to-parameter ratio = 19.8
Details

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

Youngjo Kim ^a ^*

^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-HO hydrogen bond occurs. In the crystal, the molecules are linked by O-HN and N-HO 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). For the synthesis, see: Meyer et al. (1998).

Experimental

Crystal data

C₇H₆N₄O₂
M_r = 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 radiation
= 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) T_min = 0.96, T_max = 0.98
20096 measured reflections
2452 independent reflections
1273 reflections with I > 2(I)
R_int = 0.110

Refinement

R[F² > 2(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
_max = 0.35 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N4ⁱ	0.82	1.94	2.759 (3)	173
O2-H2N3ⁱⁱ	0.82	2.00	2.817 (3)	173
N1-H101O1	0.89 (3)	2.22 (3)	2.701 (3)	113 (2)
N1-H101O2ⁱⁱⁱ	0.89 (3)	2.40 (3)	3.034 (3)	129 (2)
C3-H3N2ⁱⁱ	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
Gallardo, H., Meyer, E. & Vencato, I. (1995). Acta Cryst. C51, 2430-2432.
Meyer, E., Zucco, C. & Gallardo, H. (1998). J. Mater. Chem., 8, 1351-1354.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds