N′-[(E)-2,3-Dihy­droxy­benzyl­idene]-2-meth­oxy­benzohydrazide

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

doi:10.1107/S1600536812042390

Volume 68
Part 12
Page o3256
December 2012

Received 5 October 2012
Accepted 10 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.115
Data-to-parameter ratio = 12.7
Details

N'-[(E)-2,3-Dihydroxybenzylidene]-2-methoxybenzohydrazide

Muhammad Taha,^a M. Syukri. Baharudin,^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, Malaysia,^cFaculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam, 42300, Selangor, 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

The title compound, C₁₅H₁₄N₂O₄ adopts an E conformation about the azomethine double bond. Intramolecular N-HO and O-HN hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, molecules are linked by O-HO and C-HO hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Related literature

For applications and the biological activity of Schiff bases, see: Panneerselvam et al. (2009); Khan et al. (2009); Jarahpour et al. (2007). For related structures, see: Baharudin et al. (2012); Taha et al. (2012); Promdet et al. (2011).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Orthorhombic, P b c a
a = 14.1479 (17) Å
b = 8.6567 (11) Å
c = 22.570 (3) Å
V = 2764.2 (6) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 273 K
0.56 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.945, T_max = 0.996
15288 measured reflections
2574 independent reflections
1658 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.115
S = 1.03
2574 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3-H3AO1ⁱ	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4-H4AN2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8-H8AO3ⁱⁱ	0.93	2.33	3.189 (2)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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: PV2594 ).

References

Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jarahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules. 12, 1720-1730.
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Panneerselvam, P., Rather, B. A., Reddy, D. R. S. & Kumar, R. N. (2009). Eur. J. Med. Chem. 44, 2328-2333.
Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.

organic compounds