N′-[(3-Methyl-2-thien­yl)carbon­yl]isonicotinohydrazide

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536809033030

Volume 65
Part 9
Pages o2235-o2236
September 2009

Received 17 August 2009
Accepted 19 August 2009
Online 26 August 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 26.4
Details

N'-[(3-Methyl-2-thienyl)carbonyl]isonicotinohydrazide

H. S. Naveenkumar,^a Amirin Sadikun,^a ⁺ Pazilah Ibrahim,^a Jia Hao Goh ^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, C₁₂H₁₁N₃O₂S, the pyridine ring is inclined to the thiophene ring, forming a dihedral angle of 34.96 (7)°. The mean plane through the hydrazide unit forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thiophene rings. The two O atoms are twisted away from each other, as indicated by the C-N-N-C torsion angle of -81.27 (15)°. In the crystal structure, molecules are linked into an extended three-dimensional network by intermolecular N-HN, N-HO and C-HO hydrogen bonds. The crystal structure also features a short SO [3.2686 (10) Å] interaction and a weak intermolecular C-H [pi] interaction.

Related literature

For general background to and application of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden et al. (2000). For the preparation of the title compound, see: Besra et al. (1993). For bond-length data, see: Allen et al. (1987). For a closely related structure, see: Naveenkumar et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₂H₁₁N₃O₂S
M_r = 261.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9206 (1) Å
b = 10.7552 (2) Å
c = 12.4934 (2) Å
V = 1198.65 (3) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 100 K
0.58 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.861, T_max = 0.961
17333 measured reflections
4355 independent reflections
4078 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.097
S = 1.05
4355 reflections
165 parameters
H-atom parameters constrained
_max = 0.79 e Å^-3
_min = -0.43 e Å^-3
Absolute structure: Flack (1983), 1856 Friedel pairs
Flack parameter: -0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2N1ⁱ	0.86	2.14	2.9068 (17)	149
N3-H1N3O2ⁱⁱ	0.86	1.99	2.8034 (15)	158
C4-H4AO1ⁱⁱⁱ	0.93	2.58	3.2047 (17)	125
C10-H10AO2^iv	0.93	2.51	3.3928 (19)	159
C11-H11ACg1^v	0.93	2.80	3.3760 (17)	121
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is centroid of the C1/C2/N1/C3-C5 ring.

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: IS2451 ).

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). HSNK and JHG thank USM for the award of a USM Fellowship.

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.
Besra, G. S., Minnikin, D. E., Wheeler, P. R. & Ratledge, C. (1993). Chem. Phys. Lipids, 66, 23-34.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479-2513.
Maccari, R., Ottanà, R. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 2509-2513.
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.
Slayden, R. A. & Barry, C. E. (2000). Microbes Infect. 2, 659-669.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds