2-(1,3-Benzothia­zol-2-yl)guanidine

Shaaban Kamel Mohamed; Mahmoud A A El-Remaily; Ahmed M Soliman; Atash V Gurbanov; Seik Weng Ng

doi:10.1107/S160053681100732X

. 2011 Mar 5;67(Pt 4):o786. doi: 10.1107/S160053681100732X

2-(1,3-Benzothiazol-2-yl)guanidine

Shaaban Kamel Mohamed ^a, Mahmoud A A El-Remaily ^b, Ahmed M Soliman ^b, Atash V Gurbanov ^c, Seik Weng Ng ^d,^*

PMCID: PMC3099861 PMID: 21754077

Abstract

In the title comound, C₈H₈N₄S, one of the two independent molecules is essentially planar (r.m.s. deviation = 0.025 Å), while the other is slightly buckled (r.m.s. deviation = 0.131 Å) with the guanidine unit bent out of the plane of the fused-ring system by 16.8 (1)°. In the crystal, intermolecular N—H⋯N hydrogen bonds between the two independent molecules give rise to a hydrogen-bonded dimer. Addtional weak intermolecular N—H⋯N hydrogen bonds connect these dimers into chains along [010]. An intramolecular N—H⋯N hydrogen bond is also observed in each independent molecule.

Related literature

For the synthesis, see: Dolzhenko et al. (2006 ▶).

Experimental

Crystal data

C₈H₈N₄S
M _r = 192.24
Orthorhombic,
a = 10.2970 (3) Å
b = 10.0817 (3) Å
c = 33.5158 (11) Å
V = 3479.32 (18) Å³
Z = 16
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 295 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII diffractometer
35704 measured reflections
3996 independent reflections
3345 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.13
3996 reflections
267 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100732X/lh5214sup1.cif

e-67-0o786-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100732X/lh5214Isup2.hkl

e-67-0o786-Isup2.hkl^{(195.9KB, 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
N3—H31⋯N1	0.86 (1)	2.00 (2)	2.679 (2)	134 (2)
N3—H32⋯N2ⁱ	0.86 (1)	2.40 (2)	3.228 (2)	161 (2)
N4—H41⋯N6	0.86 (1)	2.25 (1)	3.084 (3)	165 (3)
N4—H42⋯N8ⁱ	0.86 (1)	2.50 (2)	3.350 (3)	176 (2)
N7—H71⋯N5	0.86 (1)	2.03 (2)	2.717 (3)	136 (2)
N8—H81⋯N2	0.86 (1)	2.24 (1)	3.096 (3)	177 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The title compound was synthesized as an intermediate for the synthesis of other heterocyclic compounds (Dolzhenko et al., 2006). In the title comound, C₈H₈N₄, one of the two independent molecules of is essentially planar (r.m.s. deviation 0.025 Å) while the other is slightly buckled (r.m.s. deviation 0.131 Å) with the guanidine unit bent out of the plane of the fused-ring system by 16.8 (1) °. In the crystal a pair of intermolecular N-H···N hydrogen bonds between the two independent molecules give rise to a hydrogen-bonded dimer (Fig. 1). Addtional weak intermolecular N-H···N hydrogen bonds connect these dimers into one-dimensional chains along [010].

Experimental

2-Aminothiophenol (0.050 mol) was dissolved in 10% sulfuric acid (50 ml) and to the solution was added cyanoduanidine (0.075 mol). The mixture was heated to give a clear solution. To the cool solution was added 50% sodium hydroxide (10 mol) to precipitate the product. X-ray quality crystals were recrystallized from ethanol in 90% yield. The synthesis was based on a reported procedure (Dolzhenko et al., 2006).