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Volume 66 
Part 2 
Page o291  
February 2010  

Received 4 January 2010
Accepted 5 January 2010
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.110
Data-to-parameter ratio = 19.9
Details
Open access

(E)-N'-[(E)-3-(4-Hydroxy-3-methoxyphenyl)allylidene]isonicotinohydrazide

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C16H15N3O3, the dihedral angle between the pyridine and benzene rings is 7.66 (5)°. The crystal packing is consolidated by intermolecular C-H...O and O-H...N interactions, which link the molecules into zigzag chains propagating along [010]. The chains are further linked into a three-dimensional network by N-H...O, C-H...N, C-H...O and C-H...[pi] interactions.

Related literature

For the synthesis, see: Lourenco et al. (2008[Lourenco, M. C. S., Ferreira, M. L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A. & Henriques, M. G. M. O. (2008). Eur. J. Med. Chem. 43, 1344-1347.]). For the tuberculostatic activities of isoniazid derivatives, see: Janin (2007[Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479-2513.]). For related structures, see: Naveenkumar et al. (2009a[Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Goh, J. H. & Fun, H.-K. (2009a). Acta Cryst. E65, o2235-o2236.],b[Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009b). Acta Cryst. E65, o2540-o2541.],c[Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2009c). Acta Cryst. E65, o1912.]); Shi (2005[Shi, J. (2005). Acta Cryst. E61, o3933-o3934.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O3

  • Mr = 297.31

  • Monoclinic, P 21 /c

  • a = 5.0470 (1) Å

  • b = 28.9314 (6) Å

  • c = 9.6446 (2) Å

  • [beta] = 90.010 (1)°

  • V = 1408.27 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.53 × 0.20 × 0.08 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.992

  • 33857 measured reflections

  • 4144 independent reflections

  • 3534 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.110

  • S = 1.05

  • 4144 reflections

  • 208 parameters

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 benzene ring.

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O1i 0.886 (15) 1.999 (15) 2.8622 (12) 164.4 (14)
O2-H1O2...N1ii 0.87 (2) 1.96 (2) 2.7750 (13) 156.9 (19)
C2-H2A...O3iii 0.93 2.55 3.1651 (14) 124
C4-H4A...N3iv 0.93 2.60 3.4747 (14) 156
C7-H7A...O1i 0.93 2.52 3.2405 (14) 135
C16-H16B...Cg1v 0.96 2.65 3.4556 (12) 142
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) -x+2, -y+1, -z+2; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: HB5304 ).


Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and CKQ thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). HSNK and CKQ are grateful financial assistance through a USM fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479-2513.  [CrossRef] [PubMed] [ChemPort]
Lourenco, M. C. S., Ferreira, M. L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A. & Henriques, M. G. M. O. (2008). Eur. J. Med. Chem. 43, 1344-1347.  [ISI] [CrossRef] [PubMed] [ChemPort]
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Goh, J. H. & Fun, H.-K. (2009a). Acta Cryst. E65, o2235-o2236.  [CSD] [CrossRef] [details]
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009b). Acta Cryst. E65, o2540-o2541.  [CSD] [CrossRef] [details]
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2009c). Acta Cryst. E65, o1912.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, J. (2005). Acta Cryst. E61, o3933-o3934.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2010). E66, o291  [ doi:10.1107/S1600536810000371 ]

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