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Volume 69 
Part 2 
Page o276  
February 2013  

Received 12 January 2013
Accepted 17 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 14.6
Details
Open access

(E)-N'-(4-Chlorobenzylidene)-2-methoxybenzohydrazide

aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia,bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D. E. Malaysia,cDepartment of Pharmacology and Chemistry, Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Puncak Alam, Selangor D. E., Malaysia, and dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title hydrazone derivative, C15H13ClN2O2, the dihedral angle between the benzene rings is 2.36 (2)°. An intramolecular N-H...O hydrogen bond is present. In the crystal, N-H...O and C-H...O hydrogen bonds link the molecules into chains running parallel to the b axis.

Related literature

For applications and biological activity of hydrazone derivatives, see: Khan et al. (2011[Khan, K. M., Shah, Z., Ahmad, V. U., Khan, M., Taha, M., Rahim, F., Jahan, H., Perveen, S. & Choudhary, M. I. (2011). Med. Chem. 7, 572-580.], 2012[Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Ali, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.]); Kuçukguzel et al. (1999[Kuçukguzel, S. G., Rollas, S., Kuçukguzel, I. & Kiraz, M. (1999). Eur. J. Med. Chem. 34, 1093-1100.]); Patel et al. (1984[Patel, J. M., Dave, M. P., Langalia, N. A. & Thaker, K. A. (1984). J. Indian Chem. Soc. 61, 718-720.]); Wilder (1967[Wilder, S. A. E. (1967). Arzneimittelforschung, 17, 1150-1156.]); Glasser & Doughty (1962[Glasser, A. C. & Doughty, R. M. (1962). J. Pharm. Sci. 51, 1031-1033.]). For a related structure, see: Cao (2009[Cao, G.-B. (2009). Acta Cryst. E65, o2650.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13ClN2O2

  • Mr = 288.72

  • Orthorhombic, P b c a

  • a = 12.5830 (7) Å

  • b = 9.8335 (5) Å

  • c = 23.6377 (13) Å

  • V = 2924.8 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 273 K

  • 0.48 × 0.27 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.884, Tmax = 0.974

  • 16194 measured reflections

  • 2713 independent reflections

  • 2021 reflections with I > 2[sigma](I)

  • Rint = 0.030

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

  • wR(F2) = 0.124

  • S = 1.06

  • 2713 reflections

  • 186 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2 0.76 (2) 2.04 (2) 2.632 (2) 135.7 (19)
N1-H1A...O1i 0.76 (2) 2.58 (2) 3.163 (3) 135.5 (19)
C8-H8A...O1i 0.93 2.42 3.127 (3) 132
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

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: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: RZ5038 ).


References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, G.-B. (2009). Acta Cryst. E65, o2650.  [CSD] [CrossRef] [details]
Glasser, A. C. & Doughty, R. M. (1962). J. Pharm. Sci. 51, 1031-1033.  [CrossRef] [PubMed] [ChemPort] [ISI]
Khan, K. M., Shah, Z., Ahmad, V. U., Khan, M., Taha, M., Rahim, F., Jahan, H., Perveen, S. & Choudhary, M. I. (2011). Med. Chem. 7, 572-580.  [ChemPort] [PubMed]
Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Ali, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705-710.  [ChemPort] [PubMed]
Kuçukguzel, S. G., Rollas, S., Kuçukguzel, I. & Kiraz, M. (1999). Eur. J. Med. Chem. 34, 1093-1100.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Patel, J. M., Dave, M. P., Langalia, N. A. & Thaker, K. A. (1984). J. Indian Chem. Soc. 61, 718-720.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wilder, S. A. E. (1967). Arzneimittelforschung, 17, 1150-1156.  [PubMed]


Acta Cryst (2013). E69, o276  [ doi:10.1107/S160053681300175X ]

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