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Volume 68 
Part 12 
Page o3499  
December 2012  

Received 22 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.081
Data-to-parameter ratio = 12.6
Details
Open access

N'-(3-Chlorobenzylidene)-4-hydroxybenzohydrazide

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bPCSIR Labortories Complex, Karachi, Shahrah-e-Dr. Salmuzzaman Siddiqui, Karachi 75280, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

The molecule of the title compound, C14H11ClN2O2 adopts an E conformation of the azomethine double bond and the dihedral angle between the benzene rings is 38.96 (13)°. In the crystal, molecules are linked by N-H...O and O-H...O (with the ketone O atom as acceptor) and C-H...O (with the hydroxy O atom as acceptor) hydrogen bonds, forming a three-dimensional network.

Related literature

For a related structure and background to the chemistry of the N-acylhydrazone unit, see: Taha et al. (2012[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.]). For a related structure, see: Hao (2009[Hao, Y.-M. (2009). Acta Cryst. E65, o2098.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11ClN2O2

  • Mr = 274.70

  • Orthorhombic, P n a 21

  • a = 9.0900 (8) Å

  • b = 9.9396 (9) Å

  • c = 13.8615 (12) Å

  • V = 1252.40 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.27 × 0.11 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.923, Tmax = 0.970

  • 6999 measured reflections

  • 2274 independent reflections

  • 1980 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.081

  • S = 1.02

  • 2274 reflections

  • 180 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1060 Friedel pairs

  • Flack parameter: 0.12 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1i 0.84 (2) 2.20 (2) 3.026 (3) 169 (3)
O2-H2B...O1ii 0.79 (3) 2.01 (3) 2.739 (3) 154 (3)
C4-H4A...O2iii 0.93 2.55 3.216 (3) 128
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (ii) [-x+2, -y+1, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-1].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6997 ).


Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan (project No. 20-2073) and Pakistan Academy of Sciences (PAS) for their financial support.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hao, Y.-M. (2009). Acta Cryst. E65, o2098.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3499  [ doi:10.1107/S1600536812048325 ]

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