1,4-Bis[(1H-pyrazol-1-yl)meth­yl]benzene dihydrate

Shi, A.-E.; Hou, Y.-J.; Zhang, Y.-M.; Hou, G.-F.; Gao, J.-S.

doi:10.1107/S1600536809007521

Volume 65
Part 4
Page o690
April 2009

Received 19 February 2009
Accepted 2 March 2009
Online 6 March 2009

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.123
Data-to-parameter ratio = 18.6
Details

1,4-Bis[(1H-pyrazol-1-yl)methyl]benzene dihydrate

Ai-E Shi,^a Yan-Jun Hou,^a Yi-Ming Zhang,^a Guang-Feng Hou ^a and Jin-Sheng Gao ^a ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hgf1000@163.com

The asymmetric unit of the title compound, C₁₄H₁₄N₄·2H₂O consists of two half-molecules of the main molecule, each situated on an inversion center, and two molecules of water. One-dimensional chains of water molecules are built up by O-HO hydrogen bonds which are then linked with the main molecule via O-HN hydrogen bonds, forming a two-dimensional supramolecular network in the ac plane.

Related literature

For background and the synthesis, see: Chang et al. (1993). For similar structures, see: Bourne et al. (2006).

Experimental

Crystal data

C₁₄H₁₄N₄·2H₂O
M_r = 274.32
Monoclinic, P 2₁ /c
a = 4.680 (2) Å
b = 18.640 (8) Å
c = 16.974 (10) Å
= 91.15 (2)°
V = 1480.6 (13) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 291 K
0.29 × 0.27 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.956, T_max = 0.984
14065 measured reflections
3361 independent reflections
1735 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.123
S = 1.00
3361 reflections
181 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H15N4	0.85	2.08	2.929 (3)	178
O1-H16O2ⁱ	0.85	1.87	2.717 (2)	177
O2-H17N2ⁱⁱ	0.85	2.08	2.923 (2)	170
O2-H18O1	0.85	1.89	2.733 (2)	172
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2236 ).

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20872030), the Research Foundation of Heilongjiang Provincial Education Department (grant No. 11513073), the Project of the Special Fund of the Science and Technology Innovation People of Harbin (grant No. RC2006QN018001) and Heilongjiang University.

References

Bourne, S. A., De Villiers, K. & Egan, T. J. (2006). Acta Cryst. C62, o53-o57.
Chang, W.-K., Sheu, S.-C., Lee, G.-H., Wang, Y., Ho, T.-I. & Lin, Y.-C. (1993). Dalton Trans. pp. 687-694.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds