(IUCr) 5-Bromo-1H-indole-3-carbaldehyde thiosemicarbazone

Volume 64
Part 5
Page o918
May 2008

Received 27 March 2008
Accepted 20 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.025
wR = 0.066
Data-to-parameter ratio = 15.9
Details

5-Bromo-1H-indole-3-carbaldehyde thiosemicarbazone

Mohd. Razali Rizal,^a Hapipah Mohd. Ali ^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 essentially planar title molecule, C₁₀H₉BrN₄S, the C=N double bond is in a trans configuration. In the crystal structure, the S atom acts as a hydrogen-bond acceptor for the aromatic NH, aliphatic NH and terminal NH₂ groups of three symmetry-related molecules, forming a weak hydrogen-bonded layer structure.

Related literature

For a previous synthesis of the title compound, see: Dubey & Babu (2006). For related literature, see: Doyle et al. (1956); French & Blanz (1966); Fukukawa et al. (1966); Libermann et al. (1953); Usi (1968); Weller et al. (1954).

Experimental

Crystal data

C₁₀H₉BrN₄S
M_r = 297.18
Triclinic, $[P \overline 1]$
a = 6.7731 (2) Å
b = 8.7551 (2) Å
c = 10.6539 (2) Å
= 69.280 (1)°
= 79.969 (1)°
= 72.886 (1)°
V = 563.00 (2) Å³
Z = 2
Mo K radiation
= 3.81 mm^-1
T = 100 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.381, T_max = 0.516 (expected range = 0.344-0.467)
6176 measured reflections
2563 independent reflections
2281 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.066
S = 1.06
2563 reflections
161 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1nS1ⁱ	0.88 (1)	2.60 (2)	3.390 (2)	150 (3)
N3-H3nS1ⁱⁱ	0.88 (1)	2.65 (1)	3.508 (2)	167 (2)
N4-H4n1S1ⁱⁱⁱ	0.88 (1)	2.74 (1)	3.569 (2)	158 (2)
Symmetry codes: (i) x, y+1, z-1; (ii) -x, -y+1, -z+2; (iii) -x, -y, -z+2.

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: LH2609 ).

Acknowledgements

We thank the Science Fund (12-02-03-2031) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Doyle, F. P., Ferrier, W., Holland, D. O., Mehta, M. D. & Nayler, J. H. C. (1956). J. Chem. Soc. pp. 2853-2857.
Dubey, P. K. & Babu, B. (2006). Ind. J. Heterocycl. Chem. 15, 209-219.
French, F. A. & Blanz, E. J. (1966). J. Med. Chem. 9, 585-589.
Fukukawa, F., Isao, Y., Seno, T., Sasaki, M., Naito, M. & Shunji, T. (1966). Yakaguka Zasshi, 86, 801-804.
Libermann, D., Moyeux, M., Rouaix, A., Maillard, J., Hengl, L., Himbert, J. & Theraplix, M. (1953). Bull. Soc. Chim. Fr. pp. 957-962.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Usi, Y. (1968). Ann. Rep. Takeda Res. Lab. 27, 144-158.
Weller, L. E., Sell, H. M. & Gotshall, R. Y. (1954). J. Am. Chem. Soc. 76, 1959.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds