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

Saad, S.M.; Fatima, I.; Perveen, S.; Khan, K.M.; Yousuf, S.

doi:10.1107/S1600536812048325

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 (C-C) = 0.004 Å
R = 0.037
wR = 0.081
Data-to-parameter ratio = 12.6
Details

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

Syed Muhammad Saad,^a Itrat Fatima,^a Shahnaz Perveen,^b Khalid M. Khan ^a and Sammer Yousuf ^a ^*

^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-HO and O-HO (with the ketone O atom as acceptor) and C-HO (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). For a related structure, see: Hao (2009).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 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 radiation
= 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) T_min = 0.923, T_max = 0.970
6999 measured reflections
2274 independent reflections
1980 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(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
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3
Absolute structure: Flack (1983), 1060 Friedel pairs
Flack parameter: 0.12 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO1ⁱ	0.84 (2)	2.20 (2)	3.026 (3)	169 (3)
O2-H2BO1ⁱⁱ	0.79 (3)	2.01 (3)	2.739 (3)	154 (3)
C4-H4AO2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Hao, Y.-M. (2009). Acta Cryst. E65, o2098.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.

organic compounds