(2R)-N-[5-(4-Chloro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(cinnamoylamino)propanamide

Shao-Hua Li; Hui-Ming Huang; Bin-Hai Kuang; Guo-Gang Tu; Cheng-Mei Liu

doi:10.1107/S1600536808030353

. 2008 Sep 24;64(Pt 10):o2006. doi: 10.1107/S1600536808030353

(2R)-N-[5-(4-Chlorophenyl)-1,3,4-thiadiazol-2-yl]-2-(cinnamoylamino)propanamide

Shao-Hua Li ^a,^b, Hui-Ming Huang ^b, Bin-Hai Kuang ^b, Guo-Gang Tu ^b,^*, Cheng-Mei Liu ^a,^‡

PMCID: PMC2959416 PMID: 21201204

Abstract

In the title compound, C₂₀H₁₇ClN₄O₂S, the dihedral angle between the two benzene rings is 65.9 (1)°; the corresponding angle between the 4-chlorophenyl and thiadiazole rings is 3.4 (8)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The structure displays intermolecular N—H⋯O, C—H⋯N, C—H⋯S and C—H⋯O hydrogen bonding.

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: Fun et al. (2008 ▶); Gowda et al. (2008 ▶) Thiruvalluvar et al. (2008 ▶).

Experimental

Crystal data

C₂₀H₁₇ClN₄O₂S
M _r = 412.89
Orthorhombic,
a = 6.6324 (15) Å
b = 8.575 (2) Å
c = 34.367 (8) Å
V = 1954.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 (2) K
0.41 × 0.17 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
14721 measured reflections
4706 independent reflections
2807 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.099
S = 1.02
4706 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1876 Friedel pairs
Flack parameter: −0.12 (7)

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; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030353/gw2052sup1.cif

e-64-o2006-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030353/gw2052Isup2.hkl

e-64-o2006-Isup2.hkl^{(230.6KB, 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
N2—H2A⋯O1ⁱ	0.86	1.94	2.802 (3)	175
C7—H7A⋯N3ⁱⁱ	0.93	2.54	3.446 (3)	164
C11—H11C⋯S1ⁱⁱⁱ	0.96	2.77	3.526 (3)	136
C20—H20A⋯O2^iv	0.93	2.48	3.380 (3)	162

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

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. The structure of title compound, C₂₀H₁₇ClN₄O₂S, has orthorhombic (P2₁2₁2₁) symmetry. The dihedral angles between the p-cholobenzene and thiadiazol rings is 3.4 (8) °, the corresponding values between the two benzene rings are measured to 65.9 (1)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The enone groups are trans configurated. Bond lengths and angles are in normal ranges and comparable to those in related structures (Gowda et al., 2008; Fun et al., 2008; Thiruvalluvar et al., 2008). In the crystal structure, molecules are linked through intermolecular 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-cinnamoyl-D-alanine (5.6 mmol) and N-hydroxysuccinimide (5.6 mmol) in freshly distillation 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-choloxyphenyl)-1,3,4-thiadiazole (5.5 mmol) was added to the filtrate and the reaction mixture was stirred for 48 hr at room temperature. The solvent was removed under reduced pressure. The residual 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, the residual was recrystallized from methanol. Colorless block-shaped single crystals of the title compound suitable for X-ray diffraction analysis precipitated after several days.