(IUCr) 2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate

Volume 64
Part 6
Page o960
June 2008

Received 22 April 2008
Accepted 24 April 2008
Online 3 May 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.162
Data-to-parameter ratio = 17.2
Details

2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate

Wagee A. Yehye,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title compound, C₁₇H₁₅N₃O₂·C₂H₆O, Schiff base molecules are linked by a hydroxy-amido hydrogen bond into a helical chain running along the b axis. This chain is consolidated by two other hydrogen bonds; the ethanol solvent molecule is a hydrogen-bond donor to the amide group and a hydrogen-bond acceptor for the indolyl NH group of an adjacent Schiff base molecule.

Related literature

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide, see: Alemany et al. (1967); Fujikawa et al. (1966); Nakata et al. (1966); Singh et al. (1984).

Experimental

Crystal data

C₁₇H₁₅N₃O₂·C₂H₆O
M_r = 339.39
Monoclinic, P 2₁ /c
a = 7.5907 (1) Å
b = 11.2269 (2) Å
c = 20.3014 (3) Å
= 91.924 (1)°
V = 1729.11 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 (2) K
0.34 × 0.27 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
20827 measured reflections
3967 independent reflections
2869 reflections with I > 2(I)
R_int = 0.056

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.162
S = 1.13
3967 reflections
230 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oO2ⁱ	0.84	1.76	2.594 (2)	176
O3-H3oO2	0.84	2.02	2.843 (2)	165
N1-H1nO1	0.88	1.91	2.618 (2)	136
N3-H3nO3ⁱⁱ	0.88	1.96	2.824 (2)	168
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2238 ).

Acknowledgements

We acknowledge the SAGA grant (06-02-03-0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

References

Alemany, A., Bernabe Pajares, M. F., Fernandez Alvarez, E., Lora-Tamayo, M. & Nieto Lopez, O. (1967). Bull. Soc. Chim. Fr. pp. 780-786.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fujikawa, F., Yamashita, I., Seno, T., Sasaki, M., Naito, M. & Tsukuma, S. (1966). Yakugaku Zasshi, 86, 801-804.
Nakata, H., Harada, H. & Hirata, Y. (1966). Tetrahedron Lett. pp. 2515-2522.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, I. P., Gurtu, S., Kumar, A., Sinha, J. N., Bhargava, K. P. & Shanker, K. (1984). Archiv Pharm. (Weinheim), 317, 609-614.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds