2-Meth­oxy-N-[5-(2-methoxy­phen­yl)-1,3,4-thia­diazol-2-yl]benzamide hemi­hydrate

Li-he Yin; Rong Wan; Feng Han; Bin Wang; Jin-tang Wang

doi:10.1107/S1600536808019934

. 2008 Jul 31;64(Pt 8):o1637. doi: 10.1107/S1600536808019934

2-Methoxy-N-[5-(2-methoxyphenyl)-1,3,4-thiadiazol-2-yl]benzamide hemihydrate

Li-he Yin ^a, Rong Wan ^a,^*, Feng Han ^a, Bin Wang ^a, Jin-tang Wang ^a

PMCID: PMC2962244 PMID: 21203326

Abstract

In the molecule of the title compound, C₁₇H₁₅N₃O₃S·0.5H₂O, the thiadiazole ring is oriented with respect to the two 2-methoxyphenyl rings at dihedral angles of 3.70 (3) and 1.74 (2)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the thiadiazole ring at a dihedral angle of 1.33 (3)°. Thus, all of the rings are nearly coplanar. In the crystal structure, intermolecular O—H⋯N and C—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶).

Experimental

Crystal data

C₁₇H₁₅N₃O₃S·0.5H₂O
M _r = 350.40
Monoclinic,
a = 29.950 (6) Å
b = 14.561 (3) Å
c = 7.6520 (15) Å
β = 94.78 (3)°
V = 3325.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.937, T _max = 0.989
6340 measured reflections
3003 independent reflections
1602 reflections with I > 2σ(I)
R _int = 0.060
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.079
wR(F ²) = 0.240
S = 1.04
3003 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019934/hk2483sup1.cif

e-64-o1637-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019934/hk2483Isup2.hkl

e-64-o1637-Isup2.hkl^{(147.5KB, 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—H3A⋯O3	0.86	2.04	2.706 (5)	134
O4—H4⋯N1ⁱ	0.85	2.24	2.796 (6)	123
C14—H14A⋯O2ⁱⁱ	0.93	2.49	3.316 (6)	148

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

Acknowledgments

The authors gratefully acknowledge Professor Hua-qin Wang, Analysis Centre, Nanjing University, for providing diffractometer time.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C2-C7), B (S/N1/N2/C8/C9) and C (C12-C17) are, of course, planar. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a six-membered planar ring D (N3/H3A/O3/C10/C12/C13). The dihedral angles between the rings are A/B = 3.70 (3)°, A/C = 2.81 (3)°, A/D = 2.45 (3)°, B/C = 1.74 (2)°, B/D = 1.33 (3)° and C/D = 0.90 (3)°. So, all of the rings are nearly coplanar.

In the crystal structure, intermolecular O-H···N and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For preparation of the title compound, a solution of 5-(2-methoxyphenyl) -1,3,4-thiadiazol-2-amine (5 mmol) in pyridine (50 ml) was cooled to 273 K. To this solution, 2-methoxybenzoyl chloride (5 mmol) was added via a drop funnel over period of 30 min. The mixture was stirred at 273 K for 1 h, raised to room temperature and reacted for 1 h. The pyridine was distilled and the solid residue was recrystallized from ethanol to give the title compound (m.p. 513-514 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.