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

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810000371

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.110
Data-to-parameter ratio = 19.9
Details

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

H. S. Naveenkumar,^a Amirin Sadikun,^a ⁺ Pazilah Ibrahim,^a Ching Kheng Quah ^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, C₁₆H₁₅N₃O₃, the dihedral angle between the pyridine and benzene rings is 7.66 (5)°. The crystal packing is consolidated by intermolecular C-HO and O-HN interactions, which link the molecules into zigzag chains propagating along [010]. The chains are further linked into a three-dimensional network by N-HO, C-HN, C-HO and C-H [pi] interactions.

Related literature

For the synthesis, see: Lourenco et al. (2008). For the tuberculostatic activities of isoniazid derivatives, see: Janin (2007). For related structures, see: Naveenkumar et al. (2009a,b,c); Shi (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₆H₁₅N₃O₃
M_r = 297.31
Monoclinic, P 2₁ /c
a = 5.0470 (1) Å
b = 28.9314 (6) Å
c = 9.6446 (2) Å
= 90.010 (1)°
V = 1408.27 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.950, T_max = 0.992
33857 measured reflections
4144 independent reflections
3534 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(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
_max = 0.43 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
N2-H1N2O1ⁱ	0.886 (15)	1.999 (15)	2.8622 (12)	164.4 (14)
O2-H1O2N1ⁱⁱ	0.87 (2)	1.96 (2)	2.7750 (13)	156.9 (19)
C2-H2AO3ⁱⁱⁱ	0.93	2.55	3.1651 (14)	124
C4-H4AN3^iv	0.93	2.60	3.4747 (14)	156
C7-H7AO1ⁱ	0.93	2.52	3.2405 (14)	135
C16-H16BCg1^v	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); cell refinement: SAINT (Bruker, 2009); 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: 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.
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479-2513.
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.
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Goh, J. H. & Fun, H.-K. (2009a). Acta Cryst. E65, o2235-o2236.
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009b). Acta Cryst. E65, o2540-o2541.
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2009c). Acta Cryst. E65, o1912.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, J. (2005). Acta Cryst. E61, o3933-o3934.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds