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Volume 69 
Part 10 
Page o1591  
October 2013  

Received 17 September 2013
Accepted 22 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.123
Data-to-parameter ratio = 15.4
Details
Open access

N,N'-(2-Hydroxypropane-1,3-diyl)bis(2-hydroxybenzamide) monohydrate

aLaboratoire de Chimie Inorganiue et d'Environment, Université def Tlemcen, BP 119, Tlemcen, 13 000, Algeria,bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 , Algeria,cLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif, 19000 , Algeria, and dCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title hydrate, C17H18N2O5·H2O, the complete organic molecule is generated by a crystallographic mirror plane with one C and one O atom lying on the mirror plane. The O atom of the water molecule has m site symmetry. Two symmetry-related intramolecular O-H...O hydrogen bonds complete S(6) rings in the organic molecule. In the crystal, the components are linked into (010) sheets by O-H...O and N-H...O hydrogen bonds.

Related literature

For the synthesis of similar compounds and their complexes see: Kumar & Debashis (2006[Kumar, P. N. & Debashis, R. (2006). J. Chem. Res. pp. 632-635.]); Azam et al. (2012[Azam, M., Zahid, H., Warad, I., Al-Resayes, S. I., Shahnawaz Khan, M., Shakir, M., Trzesowska-Kruszynska, A. & Kruszynski, R. (2012). Dalton Trans. 41, 10854-10864.]); Sarkar (1999[Sarkar, B. (1999). Chem. Rev. 99, 2535-2544.]); Louhibi et al. (2007[Louhibi, S., Yacouta, A., Vendier, L., Costes, J. P. & Tuchagues, J. P. (2007). Polyhedron, 26, 3448-3454.]); Kui et al. (2009[Kui, C., Zheng, Q. Z., Qian, Y., Shi, L., Jing Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 7, 7861-7871.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N2O5·H2O

  • Mr = 348.35

  • Orthorhombic, P n m a

  • a = 12.8969 (10) Å

  • b = 28.001 (2) Å

  • c = 4.5330 (4) Å

  • V = 1637.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 150 K

  • 0.38 × 0.12 × 0.04 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.877, Tmax = 0.996

  • 7880 measured reflections

  • 1904 independent reflections

  • 1195 reflections with I > 2[sigma](I)

  • Rint = 0.062

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

  • wR(F2) = 0.123

  • S = 1.04

  • 1904 reflections

  • 124 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1Wi 0.96 (3) 1.82 (3) 2.778 (3) 179 (3)
O1W-H1W...O6ii 0.92 (2) 1.92 (2) 2.827 (2) 174 (2)
O13-H13...O6 0.84 1.75 2.500 (2) 147
N4-H4...O13iii 0.88 2.07 2.915 (2) 160
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y, z+1; (iii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CRYSCAL (T. Roisnel, local program).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7142 ).


Acknowledgements

Thanks are due to MESRS and DG-RSDT (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la Direction Générale de la Recherche - Algeria) for financial support.

References

Azam, M., Zahid, H., Warad, I., Al-Resayes, S. I., Shahnawaz Khan, M., Shakir, M., Trzesowska-Kruszynska, A. & Kruszynski, R. (2012). Dalton Trans. 41, 10854-10864.  [CSD] [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kui, C., Zheng, Q. Z., Qian, Y., Shi, L., Jing Zhao, J. & Zhu, H. (2009). Bioorg. Med. Chem. 7, 7861-7871.
Kumar, P. N. & Debashis, R. (2006). J. Chem. Res. pp. 632-635.
Louhibi, S., Yacouta, A., Vendier, L., Costes, J. P. & Tuchagues, J. P. (2007). Polyhedron, 26, 3448-3454.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sarkar, B. (1999). Chem. Rev. 99, 2535-2544.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1591  [ doi:10.1107/S1600536813026184 ]

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