5-(2-Meth­oxy­phen­yl)-1,3,4-thia­diazol-2-yl 2-meth­oxy­benzoate hemihydrate

Jin-hua Yao; Bing Guo; Kang An; Jian-ning Guan

doi:10.1107/S1600536811010373

. 2011 Apr 7;67(Pt 5):o1046. doi: 10.1107/S1600536811010373

5-(2-Methoxyphenyl)-1,3,4-thiadiazol-2-yl 2-methoxybenzoate hemihydrate

Jin-hua Yao ^a, Bing Guo ^a, Kang An ^a, Jian-ning Guan ^a,^*

PMCID: PMC3089082 PMID: 21754373

Abstract

In the title compound, C₁₇H₁₄N₂O₄S·0.5H₂O, the molecule, with the exception of the two methoxyphenyl groups, is nearly planar with an r.m.s. deviation of 0.0305 Å. The two 2-methoxyphenyl rings make dihedral angles of 4.1 (3) and 2.3 (3)° with the thiadiazole ring. In the crystal, intermolecular C—H⋯O and O—H⋯N hydrogen bonds link the molecules.

Related literature

For general background to 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006 ▶). Alireza et al. (2005 ▶). Wang et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the synthesis, see: Kurzer (1971 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₄S·0.5H₂O
M _r = 356.37
Monoclinic,
a = 29.858 (6) Å
b = 14.542 (3) Å
c = 7.6710 (15) Å
β = 95.19 (3)°
V = 3317.1 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.936, T _max = 0.978
3108 measured reflections
3050 independent reflections
1881 reflections with I > 2σ(I)
R _int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.176
S = 1.00
3050 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994) ▶; cell refinement: CAD-4 EXPRESS ▶; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010373/bq2283sup1.cif

e-67-o1046-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010373/bq2283Isup2.hkl

e-67-o1046-Isup2.hkl^{(149.8KB, 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
O1W—H1W⋯N2ⁱ	1.05 (9)	1.81 (9)	2.821 (4)	159 (7)
C11—H11⋯O3ⁱⁱ	0.93	2.50	3.324 (4)	148

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

Acknowledgments

The authors would like to thank Professor Hua-qin Wang of Nanjing University, for carrying out the X-ray crystallographic analysis.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives are of great interest because of their chemical and pharmaceutical properties. Some derivatives play a key role in preparing intermediate for anticarcinogen. Recently new derivatives with 1,3,4-thiadiazole nucleus have been synthesized and evaluated for their antiproliferative effect in vitro against the cells of various human tumor cell lines (Matysiak & Opolski, 2006). Some derivatives have effective antibacterial activity. They are of great potential value for killing bacteria (Alireza et al. 2005). In addition, this kind of compounds are known to exhibit diverse biological effects, such as insecticidal activity (Wang et al. 1999).

Herein we report on the crystal structure of the titled compound, (I). The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al. 1987) and angles are within normal ranges. In this structure, there are three rings, ring A (C1/C2/C3/C4/C5/C6), ring B (N1/C7/S/C8/N2) and ring C (C10/C11/C12/C13/C14/C15), all of which are almost planar. Ring B(N1/C7/S/C8/N2) is a planar five-membered ring and the mean deviation from plane is 0.0020 Å. The dihedral angle between ring A and ring B is 4.1 (3)°, ring B and ring C is 2.3 (3)°. In the crystal structure, intermolecular C11—H11···O3 and O1W—H1W···N2 hydrogen bonds (Table 1.) link the molecules to form network structure (Fig. 2), in which they may be effective for the stabilization of the structure.

Experimental

3-Methoxy-phthalic anhydride(8 mmol) and 2-(2-methoxyphenyl)-5-hydroxy-1,3,4-thiadiazol(8 mmol) were added in ethanol(50 ml) (Kurzer, 1971). The mixture was refluxed for 5 h. Reactions were monitored by thin-layer chromatography (TLC) with visualization by ultraviolet light and then the solvent was totally evaporated. Then the white power was obtained. The solid was recrystallized from tetrahydrofuran to give the compound (I) (m.p. 520 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a mixed solution of chloroform and tetrahydrofuran.