2-Benzoyl­amino-N-[5-(4-bromo­phen­yl)-1,3,4-thia­diazol-2-yl]ethanamide

Hui-Ming Huang; Shi-Yuan Luo; Shao-Hua Li; Cheng-Mei Liu; Guo-Gang Tu

doi:10.1107/S160053680900124X

. 2009 Jan 17;65(Pt 2):o325. doi: 10.1107/S160053680900124X

2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide

Hui-Ming Huang ^a,^b, Shi-Yuan Luo ^b, Shao-Hua Li ^b, Cheng-Mei Liu ^a,^‡, Guo-Gang Tu ^b,^*

PMCID: PMC2968191 PMID: 21581930

Abstract

In the structure of the title compound, C₁₇H₁₃BrN₄O₂S, the dihedral angle between the two benzene rings is 38.5 (1)°; the angle between the 4-bromobenzene and thiadiazole rings is 1.3 (1)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The structure displays intermolecular N—H⋯O and C—H⋯O hydrogen bonding, with both interactions leading to inversion dimers.

Related literature

For 1,3,4-thiadiazole scaffold compounds and their biological activity, see: Tu et al. (2008 ▶). For the synthesis, see: Foroumadi et al. (1999 ▶); Levy & Palmer (1942 ▶); Song et al. (1992 ▶). For related structures, see: Gowda et al. (2008 ▶); Li, Huang et al. (2008 ▶); Li, Li et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₃BrN₄O₂S
M _r = 417.28
Triclinic,
a = 4.020 (4) Å
b = 13.706 (9) Å
c = 16.210 (5) Å
α = 113.334 (17)°
β = 94.018 (19)°
γ = 92.78 (2)°
V = 815.2 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 298 (2) K
0.54 × 0.17 × 0.04 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.591, T _max = 0.914
4633 measured reflections
2592 independent reflections
1097 reflections with I > 2σ(I)
R _int = 0.082

Refinement

R[F ² > 2σ(F ²)] = 0.109
wR(F ²) = 0.281
S = 0.82
2592 reflections
227 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.67 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: APEX2 (Bruker, 2004 ▶); software used to prepare material for publication: APEX2 (Bruker, 2004 ▶) and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900124X/wn2304sup1.cif

e-65-0o325-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900124X/wn2304Isup2.hkl

e-65-0o325-Isup2.hkl^{(127.3KB, 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
C16—H16A⋯O2ⁱ	0.93	2.49	3.400 (5)	168
N2—H2A⋯O1ⁱⁱ	0.86	1.99	2.835 (5)	167

Open in a new tab

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

Acknowledgments

The work was supported by the Science and Technology Research Project of JiangXi Provincial Educational Department (No. GJJ09076), the Science and Technology Planning Project of JiangXi Provincial Health Department (No. 20082015) and the Natural Science Foundation of JiangXi Province, China.

supplementary crystallographic information

Comment

In our previous work, 1,3,4-thiadiazole scaffold compounds and their biological activity have been studied (Tu et al., 2008). In view of the importance of these organic materials, the title compound (Fig. 1) was synthesized (Foroumadi et al., 1999; Levy & Palmer 1942; Song et al., 1992) and its crystal structure is reported here.

In the structure of the title compound, C₁₇H₁₃BrN₄O₂S, the dihedral angle between the p-bromobenzene and thiadiazole rings is 1.3 (1)°; the angle between the two benzene rings is 38.5 (1)°. The conformations of the N—H and C═O bonds are anti with respect to each other. Bond lengths and angles are in normal ranges and comparable to those in related structures (Gowda et al., 2008; Li, Huang et al., 2008; Li, Li et al., 2008). In the crystal structure, molecules are linked through intermolecular C—H···O and N—H···O hydrogen bonds, forming a three-dimensional network (Table 1, Figure 2).

Experimental

N,N-Dicyclohexylcarbodiimide (5.7 mmol) was added to a cooled solution of N-benzoylglycine (5.6 mmol) and N-hydroxysuccinimide (5.6 mmol) in freshly distilled dioxane (30 ml). The reaction mixture was stirred overnight at room temperature. The insoluble material was filtered off and washed with cold dioxane. 2-Amino-5-(4-bromophenyl)-1,3,4-thiadiazole (5.5 mmol) was added to the filtrate and the reaction mixture was stirred for 48 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and the insoluble material was filtered off. The filtrate was washed successively with saturated Na₂CO₃ solution (20 ml, x 3), water (20 ml, x 1), 0.1 M HCl (20 ml, x 3) and water (20 ml, x 1). The organic layer evaporated in vacuo, and the residue was recrystallized from methanol. Colorless block-shaped single crystals of the title compound suitable for X-ray diffraction analysis precipitated after several days.Yield: 37.0%; mp: 271–273°C.