[Journal logo]

Volume 70 
Part 5 
Page o612  
May 2014  

Received 10 April 2014
Accepted 18 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.097
Data-to-parameter ratio = 19.4
Details
Open access

4-Chloro-N'-[(E)-2-chloro­benzyl­idene]benzohydrazide monohydrate

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,eAnalytical Development Division, Manchester Metropolitan University, Manchester M1 5GD, England, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C14H10Cl2N2O·H2O, has a nearly planar extended conformation [C-N-N-C = -173.66 (15)°]. The dihedral angle between the aromatic rings is 4.6 (2)°. The water mol­ecules alternate with benzohydrazide mol­ecules in chains formed by O-H...O hydrogen bonds which run parallel to the a axis. These chains are linked to neighboring chains through N-H...O and C-H...O inter­actions, forming a layer parallel to (001).

Related literature

For the biological activity of hydrazone compounds, see: Koopaei et al. (2013[Koopaei, M. N., Assarzadeh, M. J., Almasirad, A., Ghasemi-Niri, S. F., Amini, M., Kebriaeezadeh, A., Koopaei, N. N., Ghadimi, M. & Tabei, A. (2013). Iran. J. Pharm. Res. 12, 721-727.]); Almasirad et al. (2005[Almasirad, A., Tajik, M., Bakhtiari, D., Shafiee, A., Abdollahi, M., Zamani, M. J. & Esmaily, H. (2005). J. Pharm. Pharm. Sci. 8, 419-425.], 2006[Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180-1185.]). For a similar structure, see: Cao (2009[Cao, G.-B. (2009). Acta Cryst. E65, o2384.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl2N2O·H2O

  • Mr = 311.16

  • Monoclinic, P 21 /n

  • a = 4.6160 (5) Å

  • b = 12.8664 (15) Å

  • c = 23.681 (3) Å

  • [beta] = 92.6760 (17)°

  • V = 1404.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.46 mm-1

  • T = 150 K

  • 0.17 × 0.08 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.78, Tmax = 0.97

  • 24861 measured reflections

  • 3511 independent reflections

  • 2604 reflections with I > 2[sigma](I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.097

  • S = 1.02

  • 3511 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.91 1.95 2.8510 (19) 168
O2-H2A...O1ii 0.84 1.93 2.7632 (19) 172
O2-H2B...O1 0.84 1.95 2.7864 (19) 172
C2-H2...O2i 0.95 2.43 3.286 (2) 150
C8-H8...O2i 0.95 2.44 3.242 (2) 143
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: RZ5119 ).


Acknowledgements

We thank Tulane University for support of the Tulane Crystallography Laboratory.

References

Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180-1185.  [CrossRef] [PubMed] [ChemPort]
Almasirad, A., Tajik, M., Bakhtiari, D., Shafiee, A., Abdollahi, M., Zamani, M. J. & Esmaily, H. (2005). J. Pharm. Pharm. Sci. 8, 419-425.  [PubMed] [ChemPort]
Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, G.-B. (2009). Acta Cryst. E65, o2384.  [CSD] [CrossRef] [IUCr Journals]
Koopaei, M. N., Assarzadeh, M. J., Almasirad, A., Ghasemi-Niri, S. F., Amini, M., Kebriaeezadeh, A., Koopaei, N. N., Ghadimi, M. & Tabei, A. (2013). Iran. J. Pharm. Res. 12, 721-727.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o612  [ doi:10.1107/S1600536814008885 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.