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Volume 69 
Part 2 
Page o277  
February 2013  

Received 11 January 2013
Accepted 17 January 2013
Online 23 January 2013

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Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.080
Data-to-parameter ratio = 12.2
Details
Open access

(E)-2-Methoxy-N'-(2,4,6-trihydroxybenzylidene)benzohydrazide

Muhammad Taha,a M. Syukri Baharudin,a Nor Hadiani Ismail,b Syed Adnan Ali Shaha,c and Sammer Yousufd*

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, C15H14N2O5, the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The molecular structure is stabilized by intramolecular O-H...N and N-H...O hydrogen bonds, generating S6 ring motifs. In the crystal, molecules are linked into a three-dimensional network by O-H...O hydrogen bonds.

Related literature

For applications and biological activity of Schiff bases, 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.]); Rada & Leto (2008[Rada, B. & Leto, T. (2008). Contrib. Microbiol. 15, 164-187.]); Almasirad et al. (2006[Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180-1185.]). For related structures, see: Taha et al. (2012[Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.]); Shen et al. (2012[Shen, T., Li, G. & Zheng, B. (2012). Acta Cryst. E68, o2034.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O5

  • Mr = 302.28

  • Orthorhombic, P 21 21 21

  • a = 6.4580 (4) Å

  • b = 13.4772 (8) Å

  • c = 16.3169 (9) Å

  • V = 1420.15 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 273 K

  • 0.34 × 0.23 × 0.21 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 = 0.964, Tmax = 0.978

  • 8414 measured reflections

  • 2643 independent reflections

  • 2481 reflections with I > 2[sigma](I)

  • Rint = 0.019
Refinement

  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.080

  • S = 1.07

  • 2643 reflections

  • 216 parameters

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1 0.84 (3) 1.88 (2) 2.6243 (18) 147 (2)
N2-H2A...O5 0.851 (19) 1.923 (19) 2.5981 (18) 135.4 (17)
O3-H2B...O4i 0.86 (2) 1.79 (2) 2.6452 (17) 175 (2)
O2-H3A...O1ii 0.93 (3) 1.92 (3) 2.8513 (18) 172 (3)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [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: RZ5037 ).

References

Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180-1185.  [CrossRef] [PubMed] [ChemPort]
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Rada, B. & Leto, T. (2008). Contrib. Microbiol. 15, 164-187.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, T., Li, G. & Zheng, B. (2012). Acta Cryst. E68, o2034.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846.  [CSD] [CrossRef] [details]

Acta Cryst (2013). E69, o277  [ doi:10.1107/S1600536813001748 ]

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