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

Mohd Razali Rizal; Hapipah Mohd Ali; Seik Weng Ng

doi:10.1107/S160053680801101X

. 2008 Apr 26;64(Pt 5):o918. doi: 10.1107/S160053680801101X

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

Mohd Razali Rizal ^a, Hapipah Mohd Ali ^a, Seik Weng Ng ^a,^*

PMCID: PMC2961179 PMID: 21202400

Abstract

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,
a = 6.7731 (2) Å
b = 8.7551 (2) Å
c = 10.6539 (2) Å
α = 69.280 (1)°
β = 79.969 (1)°
γ = 72.886 (1)°
V = 563.00 (2) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.066
S = 1.06
2563 reflections
161 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801101X/lh2609sup1.cif

e-64-0o918-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801101X/lh2609Isup2.hkl

e-64-0o918-Isup2.hkl^{(125.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S1ⁱ	0.88 (1)	2.60 (2)	3.390 (2)	150 (3)
N3—H3n⋯S1ⁱⁱ	0.88 (1)	2.65 (1)	3.508 (2)	167 (2)
N4—H4n1⋯S1ⁱⁱⁱ	0.88 (1)	2.74 (1)	3.569 (2)	158 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Indole-3-carboxaldehyde thiosemicarbazone and its substituted analogs possess useful medicinal properties; such activity has been known for a long time (Doyle et al., 1956; French & Blanz, 1966; Fukukawa et al., 1966; Libermann et al., 1953; Usi, 1968; Weller et al., 1954). The compounds, in the form of their metal derivatives, have been assesses for similar activity.

In the title compound (I) (Fig. 1), the double-bonded sulfur atom is a hydrogen-bond acceptor for the aromatic -N-H, aliphatic -N-H and terminal -NH₂ groups of three adjacent molecules, forming a weak hydrogen-bonded layer structure.

Experimental

5-Bromoindole-3-carboxaldehyde (0.3 g, 1.3 mmol) and thiosemicarbazide (0.12 g, 1.3 mmol) were heated in ethanol (50 ml) for an hour. The solvent was removed and the product and recrystallized from ethanol.