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Volume 70 
Part 1 
Pages o95-o96  
January 2014  

Received 13 December 2013
Accepted 17 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.119
Data-to-parameter ratio = 16.8
Details
Open access

2-{[5-(Pyridin-4-yl)-4-p-tolyl-4H-1,2,4-triazol-3-yl]meth­yl}acrylic acid hemi­hydrate

aDepartment of Organic Chemistry, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. A. Jurasza 2, 85-089 Bydgoszcz, Poland, and bDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland
Correspondence e-mail: akgzella@ump.edu.pl

The asymmetric unit of the title compound, 2C18H16N4O2·H2O, consists of two organic molecules and one solvent molecule. The symmetry-independent organic mol­ecules have slightly different conformations: the 1,2,4-triazole ring forms dihedral angles of 84.61 (4), 89.68 (5) and 22.38 (6)°, respectively, with the 2-propenecarbocylic, p-tolyl and 4-pyridyl groups in one independent molecule, and 71.35 (4), 82.13 (5) and 24.82 (6)°, respectively, in the second. In the crystal, mol­ecules ralated by the 21 screw axes are assembled via O-H...N and O-H...O hydrogen bonds into infinite chains and these are linked by further O-H...N hydrogen bonds into undulating sheets parallel to the bc plane. Adjacent sheets are connected by weak C-H...O inter­actions, forming a three-dimensional structure.

Related literature

For the pharmacological activity of 1,2,4-triazole derivatives, see: Amir & Shikha (2004[Amir, M. & Shikha, K. (2004). Eur. J. Med. Chem. 39, 535-545.]); El-Serwy et al. (2013[El-Serwy, W. S., Mohamed, N. A., Abbas, E. M. & Abdel-Rahman, R. F. (2013). Res. Chem. Intermed. 39, 2543-2554.]); McDowell et al. (2010[McDowell, M., Gonzales, S. R., Kumarapperuma, S. C., Jeselnik, M., Arterburn, J. B. & Hanley, K. A. (2010). Antiviral Res. 87, 78-80.]); Modzelewska-Banachiewicz, Paprocka et al. (2012[Modzelewska-Banachiewicz, B., Paprocka, R., Mazur, L., Saczewski, J., Kutkowska, J., St\,epien, D. K. & Cyranski, M. (2012). J. Mol. Struct. 1022, 211-219.]); Modzelewska-Banachiewicz, Ucherek et al. (2012[Modzelewska-Banachiewicz, B., Ucherek, M., Zimecki, M., Kutkowska, J., Kaminska, T., Morak-Mlodawska, B., Paprocka, R., Szulc, M., Lewandowski, G., Marciniak, J. & Bobkiewicz-Kozlowska, T. (2012). Arch. Pharm. Chem. Life Sci. 345, 486-494.]); Siddiqui & Ahsan (2010[Siddiqui, N. & Ahsan, W. (2010). Eur. J. Med. Chem. 45, 1536-1543.]); Sztanke et al. (2008[Sztanke, K., Tuzimski, T., Rzymowska, J., Pasternak, K. & Kandefer-Szerszen, M. (2008). Eur. J. Med. Chem. 43, 404-419.]); Wang et al. (2000[Wang, W., Wang, S., Liu, Y., Dong, G., Cao, Y., Miao, Z., Yao, J., Zhang, W. & Sheng, C. (2000). Eur. J. Med. Chem. 45, 6020-6026.]).

[Scheme 1]

Experimental

Crystal data
  • 2C18H16N4O2·H2O

  • Mr = 658.71

  • Monoclinic, P 21 /n

  • a = 10.0344 (1) Å

  • b = 16.1485 (2) Å

  • c = 20.1650 (3) Å

  • [beta] = 98.699 (1)°

  • V = 3229.96 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 130 K

  • 0.55 × 0.30 × 0.10 mm

Data collection
  • Agilent Xcalibur Atlas diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.991, Tmax = 1.000

  • 22090 measured reflections

  • 7724 independent reflections

  • 6542 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.119

  • S = 1.03

  • 7724 reflections

  • 460 parameters

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

  • [Delta][rho]max = 0.80 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O11A-H11A...N22Ai 0.92 (3) 1.77 (3) 2.6838 (17) 178 (2)
O11B-H11B...O25 0.98 (2) 1.59 (2) 2.5619 (16) 174 (2)
O25-H25A...N1A 0.86 (2) 2.00 (2) 2.8373 (17) 166 (2)
O25-H25B...N22Bii 0.94 (2) 1.87 (2) 2.8050 (18) 171 (2)
C6A-H6A2...O10Biii 0.97 2.51 3.3300 (18) 142
C24A-H24A...O10Biv 0.93 2.41 3.2683 (18) 153
C24B-H24B...O10Aiii 0.93 2.57 3.4628 (18) 162
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6951 ).


References

Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Amir, M. & Shikha, K. (2004). Eur. J. Med. Chem. 39, 535-545.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
El-Serwy, W. S., Mohamed, N. A., Abbas, E. M. & Abdel-Rahman, R. F. (2013). Res. Chem. Intermed. 39, 2543-2554.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
McDowell, M., Gonzales, S. R., Kumarapperuma, S. C., Jeselnik, M., Arterburn, J. B. & Hanley, K. A. (2010). Antiviral Res. 87, 78-80.  [CrossRef] [ChemPort] [PubMed]
Modzelewska-Banachiewicz, B., Paprocka, R., Mazur, L., Saczewski, J., Kutkowska, J., St\,epien, D. K. & Cyranski, M. (2012). J. Mol. Struct. 1022, 211-219.
Modzelewska-Banachiewicz, B., Ucherek, M., Zimecki, M., Kutkowska, J., Kaminska, T., Morak-Mlodawska, B., Paprocka, R., Szulc, M., Lewandowski, G., Marciniak, J. & Bobkiewicz-Kozlowska, T. (2012). Arch. Pharm. Chem. Life Sci. 345, 486-494.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddiqui, N. & Ahsan, W. (2010). Eur. J. Med. Chem. 45, 1536-1543.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sztanke, K., Tuzimski, T., Rzymowska, J., Pasternak, K. & Kandefer-Szerszen, M. (2008). Eur. J. Med. Chem. 43, 404-419.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Wang, W., Wang, S., Liu, Y., Dong, G., Cao, Y., Miao, Z., Yao, J., Zhang, W. & Sheng, C. (2000). Eur. J. Med. Chem. 45, 6020-6026.  [CrossRef]


Acta Cryst (2014). E70, o95-o96   [ doi:10.1107/S1600536813034077 ]

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