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Volume 68 
Part 4 
Page o1079  
April 2012  

Received 10 March 2012
Accepted 11 March 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 9.6
Details
Open access

N'-(5-Chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide

aSchool of Chemistry and Environmental Engineering, Chongqing Three Gorges University, Chongqing 404000, People's Republic of China
Correspondence e-mail: tanyao1984@yahoo.cn

The asymmetric unit of the title compound, C15H13ClN2O3, contains two independent hydrazone molecules. Each molecule adopts an E configuration with respect to the methylidene unit and forms an intramolecular O-H...N hydrogen bond. The principal difference between the two unique molecules is the relative orientation of the two benzene rings, the dihedral angles between them being 4.0 (3) and 65.9 (3)°, respectively. In the crystal, molecules are linked through N-H...O hydrogen bonds, forming chains running along the c axis.

Related literature

For similar hydrazone derivatives, see: Li (2012[Li, X.-Y. (2012). Acta Cryst. E68, o709.]); Zhu et al. (2012[Zhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559.]); Shen et al. (2012[Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.]); Liu et al. (2011[Liu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139.]); Lei (2011[Lei, Y. (2011). Acta Cryst. E67, o162.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13ClN2O3

  • Mr = 304.72

  • Monoclinic, P 21 /c

  • a = 17.569 (3) Å

  • b = 8.367 (2) Å

  • c = 19.454 (3) Å

  • [beta] = 93.683 (3)°

  • V = 2853.8 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 298 K

  • 0.11 × 0.08 × 0.07 mm

Data collection
  • Bruker SMART CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.981

  • 11127 measured reflections

  • 3752 independent reflections

  • 2545 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • [theta]max = 22.7°

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.02

  • 3752 reflections

  • 389 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.15 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
N4-H4B...O2i 0.89 (1) 1.98 (1) 2.843 (3) 164 (2)
N2-H2...O5 0.89 (1) 2.01 (1) 2.883 (3) 166 (2)
O4-H4...N3 0.82 1.82 2.540 (3) 145
O1-H1...N1 0.82 1.80 2.526 (3) 146
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, 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: 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5210 ).


References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Lei, Y. (2011). Acta Cryst. E67, o162.  [CrossRef] [details]
Li, X.-Y. (2012). Acta Cryst. E68, o709.  [CrossRef] [details]
Liu, H., Cai, Y., Wu, J., Li, Z. & Li, G. (2011). Acta Cryst. E67, o2139.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, X.-H., Zhu, L.-X., Shao, L.-J. & Zhu, Z.-F. (2012). Acta Cryst. E68, o297.  [CSD] [CrossRef] [details]
Zhu, Z.-F., Shao, L.-J. & Shen, X.-H. (2012). Acta Cryst. E68, o559.  [CrossRef] [details]


Acta Cryst (2012). E68, o1079  [ doi:10.1107/S1600536812010707 ]

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