4-Amino-3,5-bis­(2-pyrid­yl)-4H-1,2,4-triazole–benzene-1,2,3-tricarboxylic acid–water (1/1/2)

Jiang, X.-J.

doi:10.1107/S1600536810010470

Volume 66
Part 5
Pages o1075-o1076
May 2010

Received 10 March 2010
Accepted 20 March 2010
Online 14 April 2010

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.105
Data-to-parameter ratio = 11.8
Details

4-Amino-3,5-bis(2-pyridyl)-4H-1,2,4-triazole-benzene-1,2,3-tricarboxylic acid-water (1/1/2)

Xiu-Juan Jiang ^a ^*

^aSchool of Biological and Chemical Engineering, Jiaxing University, Zhejiang Jiaxing 314001, People's Republic of China
Correspondence e-mail: jxj1106@163.com

Cocrystallization of 4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole (2-bpt) with hemimellitic acid (benzene-1,2,3-tricarboxylic acid) dihydrate (H₃HMA·2H₂O) produces the supramolecular title compound, C₁₂H₁₀N₆·C₉H₆O₆·2H₂O. Intermolecular N-HN hydrogen bonds are observed between the terminal pyridyl and amino groups of the 2-bpt molecule and the dihedral angles between the central ring and the pendant pyridine rings are 3.4 (7) and 13.8 (7)°. In the structure, homosynthons of graph set R₂²(8) are observed to form centrosymmetric H₃HMA dimers, which are extended into a two-dimensional supramolecular layer via intermolecular O-HN and C-HO hydrogen bonds and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.541 (3) Å]. In addition, interlayer uncoordinated water molecules connect the layers through O-HO hydrogen bonds, generating a three-dimensional network.

Related literature

For background to the use of carboxylic acid in synthesis, see: Kuduva et al. (1999); Das et al. (2006). For the structure of trimesic acid, see: Biradha et al. (1998); Paz et al. (2003). For co-crystals of H₃HMA, see: Dale et al. (2004); Du et al. (2005); For organic crystals of 4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole (2-bpt), see: Mernari et al. (1998); Ramos Silva et al. (2008). For the preparation of 2-bpt, see: Bentiss et al. (1999).

Experimental

Crystal data

C₁₂H₁₀N₆·C₉H₆O₆·2H₂O
M_r = 484.43
Triclinic, $[P \overline 1]$
a = 8.4266 (10) Å
b = 8.6317 (10) Å
c = 15.7318 (18) Å
= 75.152 (12)°
= 77.179 (12)°
= 88.417 (13)°
V = 1078.0 (2) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 294 K
0.24 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.967, T_max = 0.980
5932 measured reflections
3765 independent reflections
2832 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.105
S = 1.05
3765 reflections
320 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O7ⁱ	0.82	1.79	2.600 (2)	171
O3-H3N3ⁱⁱ	0.82	1.90	2.698 (2)	166
O5-H5O6ⁱⁱⁱ	0.82	1.85	2.674 (2)	177
N5-H5AN6	0.90	2.08	2.786 (2)	134
N5-H5BN1	0.90	2.17	2.804 (2)	127
O7-H7AO8^iv	0.85	1.92	2.766 (2)	172
O7-H7BO4^v	0.85	2.06	2.908 (2)	173
O8-H8AN2	0.85	2.03	2.881 (2)	177
O8-H8BO2^vi	0.85	2.12	2.867 (2)	147
C14-H14O8	0.93	2.51	3.348 (2)	149
C19-H19O4^vii	0.93	2.58	3.427 (2)	152
C20-H20O6^viii	0.93	2.47	3.386 (3)	167
Symmetry codes: (i) x-1, y, z; (ii) x-1, y-1, z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y, -z+1; (vi) x+1, y+1, z; (vii) -x+2, -y+1, -z; (viii) -x+2, -y+2, -z.

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2426 ).

Acknowledgements

The author gratefully acknowledges the financial support of Tianjin Normal University and Jiaxing University.

References

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Biradha, K., Dennis, D., MacKinnon, V. A., Sharma, C. V. K. & Zaworotko, M. J. (1998). J. Am. Chem. Soc. 120, 11894-11903.
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Dale, S. H., Elsegood, M. R. J. & Coombs, A. E. L. (2004). CrystEngComm, 6, 328-335 .
Das, D. & Desiraju, G. R. (2006). CrystEngComm, 8, 674-679.
Du, M., Zhang, Z.-H. & You, Y.-P. (2005). Acta Cryst. C61, o574-o576.
Kuduva, S. S., Craig, D. C., Nangia, A. & Desiraju, G. R. (1999). J. Am. Chem. Soc. 121, 1936-1944.
Mernari, B., El Azhar, M., El Attari, H., Lagrenée, M. & Pierrot, M. (1998). Acta Cryst. C54, 1983-1986.
Paz, F. A. A. & Klinowski, J. (2003). CrystEngComm, 5, 238-244.
Ramos Silva, M., Silva, J. A., Martins, N. D., Matos Beja, A. & Sobral, A. J. F. N. (2008). Acta Cryst. E64, o1762.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds