Tris(2-hydroxy­ethyl)ammonium 1,3-benzo­thia­zole-2-thiol­ate

Ji-Qin Zhu; Hua-Cai Fang; Bi-Yun Chen; Mao-Song Feng; Jing-Ning Li

doi:10.1107/S160053680902248X

. 2009 Jun 20;65(Pt 7):o1640. doi: 10.1107/S160053680902248X

Tris(2-hydroxyethyl)ammonium 1,3-benzothiazole-2-thiolate

Ji-Qin Zhu ^a, Hua-Cai Fang ^a, Bi-Yun Chen ^a, Mao-Song Feng ^a, Jing-Ning Li ^a,^*

PMCID: PMC2969305 PMID: 21582904

Abstract

In the title compound, C₆H₁₆NO₃ ⁺·C₇H₄NS₂ ⁻, the cations and anions are connected by O—H⋯N and O—H⋯S hydrogen bonding. Weak C—H⋯O hydrogen bonding between adjacent cations helps to stabilize the crystal structure.

Related literature

For related structures, see Bethge et al. (2008 ▶); Siracusa et al. (2008 ▶); Solar et al. (2008 ▶); Varlamov et al. (2005 ▶).

Experimental

Crystal data

C₆H₁₆NO₃ ⁺·C₇H₄NS₂ ⁻
M _r = 316.43
Monoclinic,
a = 16.496 (2) Å
b = 5.7184 (8) Å
c = 17.462 (3) Å
β = 111.524 (2)°
V = 1532.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.56 × 0.38 × 0.23 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.803, T _max = 0.921
7572 measured reflections
2827 independent reflections
2185 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.092
S = 1.04
2827 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902248X/xu2531sup1.cif

e-65-o1640-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902248X/xu2531Isup2.hkl

e-65-o1640-Isup2.hkl^{(138.8KB, 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
O1—H1⋯N1ⁱ	0.82	1.96	2.770 (2)	168
O2—H2⋯S2ⁱ	0.82	2.43	3.2258 (17)	165
O3—H3⋯S2	0.82	2.35	3.1621 (16)	169
C8—H8A⋯O1ⁱⁱ	0.97	2.50	3.385 (3)	151
C10—H10B⋯O3ⁱⁱⁱ	0.97	2.47	3.425 (3)	167

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

Acknowledgments

The work was supported by the National Natural Science Foundation of China (No. 20772037) and the NSF of Guangdong Province, China (No. 06025033).

supplementary crystallographic information

Comment

Some related compounds involving the 2-mercaptobenzothiazole and its derivatives has reported previously (Varlamov et al., 2005; Solar et al., 2008; Siracusa et al. 2008; Bethge et al., 2008). The crystal structure of the title compound consists of tris(2-hydroxyethyl)ammonium cations and benzothiazole-2-thiolate anions (Fig. 1). The cations and anions are connected by O—H···N and O—H···S hydrogen bonding (Table 1).

Experimental

A mixture of benzothiazole (335 mg, 2 mmol), triethanolamine (0.4 ml and 3 mmol) in ethyl acetate (20 ml) was refluxed for 20 h. The resultant yellow solution was delaminated into two layers at room temperature and then filtered. Single crystals suitable for X-ray diffraction were obtained in two day by slow diffusion of diethyl ether into a dilute solution of the title complex in ethyl acetate. The elemental analysis; calculated for C₁₃H₂₀N₂O₃S₂: C 49.37, H 6.33, N 8.86%; found: C 49.31, H 6.38, N 8.82%.