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

Baharudin, M.S.; Taha, M.; Ismail, N.H.; Shah, S.A.A.; Yousuf, S.

doi:10.1107/S160053681300175X

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 14.6
Details

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

M. Syukri. Baharudin,^a Muhammad Taha,^a Nor Hadiani Ismail,^b Syed Adnan Ali Shah ^a,^c and Sammer Yousuf ^d ^*

^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-HO hydrogen bond is present. In the crystal, N-HO and C-HO 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, 2012); Kuçukguzel et al. (1999); Patel et al. (1984); Wilder (1967); Glasser & Doughty (1962). For a related structure, see: Cao (2009).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M_r = 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 radiation
= 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) T_min = 0.884, T_max = 0.974
16194 measured reflections
2713 independent reflections
2021 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(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
_max = 0.32 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2	0.76 (2)	2.04 (2)	2.632 (2)	135.7 (19)
N1-H1AO1ⁱ	0.76 (2)	2.58 (2)	3.163 (3)	135.5 (19)
C8-H8AO1ⁱ	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); 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: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

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.
Glasser, A. C. & Doughty, R. M. (1962). J. Pharm. Sci. 51, 1031-1033.
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.
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, S. G., Rollas, S., Kuçukguzel, I. & Kiraz, M. (1999). Eur. J. Med. Chem. 34, 1093-1100.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Patel, J. M., Dave, M. P., Langalia, N. A. & Thaker, K. A. (1984). J. Indian Chem. Soc. 61, 718-720.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wilder, S. A. E. (1967). Arzneimittelforschung, 17, 1150-1156.

organic compounds