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Volume 69 
Part 5 
Pages o743-o744  
May 2013  

Received 23 March 2013
Accepted 11 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.107
Data-to-parameter ratio = 13.8
Details
Open access

5-{4'-[(5-Benzyl-2H-tetrazol-2-yl)methyl]biphenyl-2-yl}-1H-tetrazole monohydrate

aDepartment of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka, India,bDepartment of Physics, St. Philomena's College, Mysore 570 006, Karnataka, India, and cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
Correspondence e-mail: kamchem9@gmail.com, devarajegowda@yahoo.com

In the title compound, C22H18N8·H2O, the dihedral angle between the tetrazole rings is 69.58 (1)° while the terminal phenyl ring makes dihedral angles of 26.98 (8) and 39.75 (8)° with the other benzene rings. The rings of the biphenyl unit subtend a dihedral angle of 55.23 (8)°. In the crystal, the solvent water molecule is linked to the main molecule via an N-H...O hydrogen bond. In addition, C-H...N and O-H...N hydrogen bonds link the components into chains along [010]. The crystal structure also features C-H...[pi] and [pi]-[pi] interactions, with centroid-centroid distances of 3.6556 (9) and 3.826 (1) Å.

Related literature

For general background to biphenyl derivatives, see: Li et al. (2011[Li, W., Xu, Z., Sun, P., Jiang, X. & Fang, M. (2011). Org. Lett. 13, 1286-1289.]); Tomori et al. (2000[Tomori, H., Fox, J. M. & Buchwald, S. L. (2000). J. Org. Chem. 65, 5334-5341.]). For the synthesis and biological activity of tetrazole derivatives, see: Kamble et al. (2011[Kamble, R. R., Biradar, D. B., Meti, G. Y., Taj, T., Gireesh, T., Khazi, I. M., Vaidynathan, S. T., Mohandoss, R., Sridhar, B. & Parthasarathi, V. (2011). J. Chem. Sci. 123, 393-401.]); Rao & Babu (2011[Rao, S. N. & Babu, K. S. (2011). Org. Commun. 4, 105-111.]). For biological properties of tetrazole-derivatized biphenyl moieties, see: Zhang et al. (2008[Zhang, C. X., Zheng, G. J., Bi, F. Q. & Li, Y. L. (2008). Chin. Chem. Lett. 19, 759-761.]); Wang et al. (2010[Wang, P., Zheng, G., Wang, Y., Wang, X., Li, Y. & Xiang, W. (2010). Tetrahedron, 66, 5402-5406.]); Reddy et al. (2007[Reddy, K. S., Srinivasan, N., Reddy, C. R., Kolla, N., Anjaneyulu, Y., Venkatraman, S., Bhattacharya, A. & Mathad, V. T. (2007). Org. Process Res. Dev. 11, 81-85.]). For related structures, see: Zhang et al. (2004[Zhang, H., Yang, B., Zheng, Y., Yang, G., Ye, L., Ma, Y., Chen, X., Cheng, G. & Liu, S. (2004). J. Phys. Chem. 108, 9571-9573.]). For the extinction correction, see: Larson (1970[Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18N8·H2O

  • Mr = 412.45

  • Monoclinic, P 21 /c

  • a = 14.7659 (4) Å

  • b = 7.6507 (3) Å

  • c = 18.2922 (5) Å

  • [beta] = 97.153 (2)°

  • V = 2050.38 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: [psi] scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 18220 measured reflections

  • 3923 independent reflections

  • 3469 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.107

  • S = 1.00

  • 3881 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg4 and Cg5 are the centroids of the C6/N2-N5 tetrazole ring, the C8-C13 benzene ring, the C15-C20 benzene ring and the C21/C22/C28-C31 benzene ring, respectively.

D-H...A D-H H...A D...A D-H...A
C7-H71...N25i 0.99 2.59 3.514 (2) 156
N24-H241...O1ii 0.92 1.79 2.703 (2) 173
O1-H11...N27 0.83 2.35 2.950 (2) 130
C9-H91...Cg4iii 0.96 2.85 3.418 (1) 119
C12-H121...Cg1i 0.94 2.82 3.602 (1) 141
C14-H142...Cg3iv 0.96 2.72 3.676 (1) 171
C29-H291...Cg5v 0.96 2.80 3.682 (2) 153
C31-H311...Cg3vi 0.95 2.96 3.582 (1) 125
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) -x+2, -y+1, -z+1; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5301 ).


Acknowledgements

The authors thank the University Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the data collection and Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his constant support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kamble, R. R., Biradar, D. B., Meti, G. Y., Taj, T., Gireesh, T., Khazi, I. M., Vaidynathan, S. T., Mohandoss, R., Sridhar, B. & Parthasarathi, V. (2011). J. Chem. Sci. 123, 393-401.  [CSD] [CrossRef] [ChemPort]
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.
Li, W., Xu, Z., Sun, P., Jiang, X. & Fang, M. (2011). Org. Lett. 13, 1286-1289.  [ISI] [CrossRef] [ChemPort] [PubMed]
Rao, S. N. & Babu, K. S. (2011). Org. Commun. 4, 105-111.  [ChemPort]
Reddy, K. S., Srinivasan, N., Reddy, C. R., Kolla, N., Anjaneyulu, Y., Venkatraman, S., Bhattacharya, A. & Mathad, V. T. (2007). Org. Process Res. Dev. 11, 81-85.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Tomori, H., Fox, J. M. & Buchwald, S. L. (2000). J. Org. Chem. 65, 5334-5341.  [CrossRef] [PubMed] [ChemPort]
Wang, P., Zheng, G., Wang, Y., Wang, X., Li, Y. & Xiang, W. (2010). Tetrahedron, 66, 5402-5406.  [ISI] [CrossRef] [ChemPort]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.
Zhang, H., Yang, B., Zheng, Y., Yang, G., Ye, L., Ma, Y., Chen, X., Cheng, G. & Liu, S. (2004). J. Phys. Chem. 108, 9571-9573.  [ChemPort]
Zhang, C. X., Zheng, G. J., Bi, F. Q. & Li, Y. L. (2008). Chin. Chem. Lett. 19, 759-761.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o743-o744   [ doi:10.1107/S1600536813009963 ]

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