(E)-N′-(3-Benz­yloxy-4-methoxy­benzyl­idene)isonicotinohydrazide

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Loh, W.-S.; Fun, H.-K.

doi:10.1107/S1600536809037921

Volume 65
Part 10
Pages o2540-o2541
October 2009

Received 18 September 2009
Accepted 19 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.060
wR = 0.145
Data-to-parameter ratio = 25.8
Details

(E)-N'-(3-Benzyloxy-4-methoxybenzylidene)isonicotinohydrazide

H. S. Naveenkumar,^a Amirin Sadikun,^a ⁺ Pazilah Ibrahim,^a Wan-Sin Loh ^b and Hoong-Kun Fun ^b ^*⁺⁺

^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, C₂₁H₁₉N₃O₃, the pyridine ring forms a dihedral angle of 15.25 (6)° with the benzene ring. The dihedral angle between the two benzene rings is 83.66 (7)°. The methoxy group is slightly twisted away from the attached ring [C-O-C-C = 7.5 (2)°]. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N-HN and C-HO hydrogen bonds. The structure is further stabilized by C-H [pi] interactions.

Related literature

For bond-length data, see: Allen et al. (1987). For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the preparation, see: Lourenço et al. (2008). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar, Sadikun, Ibrahim, Goh & Fun (2009); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2009); Shi (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₁H₁₉N₃O₃
M_r = 361.39
Monoclinic, P 2₁ /c
a = 18.3930 (6) Å
b = 11.5574 (4) Å
c = 8.3508 (3) Å
= 93.436 (2)°
V = 1771.98 (11) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.71 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.937, T_max = 0.992
27863 measured reflections
6434 independent reflections
3841 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.145
S = 1.06
6433 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.37 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8-C13 ring.

D-HA	D-H	HA	DA	D-HA
N2-H1N2N1ⁱ	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9-H9AO1ⁱⁱ	0.93	2.55	3.3524 (17)	144
C19-H19AO3ⁱⁱⁱ	0.93	2.54	3.3960 (17)	153
C17-H17ACg1^iv	0.93	2.93	3.6694 (17)	137
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z+1; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2917 ).

Acknowledgements

This research is supported by Universiti Sains Malaysia (USM) under the University Research Grant No. 1001/PFARMASI/815005. H-KF and W-SL thank USM for the Research University Golden Goose Grant No. 1001/PFIZIK/811012. W-SL also thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under Research University Golden Goose Grant No. 1001/PFIZIK/811012. HSN is grateful for a USM fellowship for financial assistance.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479-2513.
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.
Lourenço, M. C. da S., Ferreira, M. de L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A., Henriques, M. & das, G. M. O. (2008). Eur. J. Med. Chem. 43, 1344-1347.
Maccari, R., Ottana, R. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 2509-2513.
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Goh, J. H. & Fun, H.-K. (2009). Acta Cryst. E65, o2235-o2236.
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2009). Acta Cryst. E65, o1912.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, J. (2005). Acta Cryst. E61, o3933-o3934.
Slayden, R. A. & Barry, C. E. (2000). Microbes Infect. 2, 659-669.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds