N-[4-Acetyl-5-(4-fluoro­phen­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl]acetamide

H D Kavitha; Sheetal B Marganakop; Ravindra R Kamble; K R Roopashree; H C Devarajegowda

doi:10.1107/S1600536813009367

. 2013 Apr 13;69(Pt 5):o701–o702. doi: 10.1107/S1600536813009367

N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

H D Kavitha ^a, Sheetal B Marganakop ^b, Ravindra R Kamble ^b, K R Roopashree ^c, H C Devarajegowda ^c,^*

PMCID: PMC3648237 PMID: 23723857

Abstract

The title molecule, C₁₂H₁₂FN₃O₂S, shows a short intramolecular S⋯O contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring and the benzene ring is 86.82 (11)°. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds generate an R ₂ ¹(6) graph-set motif between adjacent molecules. Pairs of futher C—H⋯O hydrogen bonds form inversion dimers with R ₂ ²(8) ring motifs. These combine to generate a three-dimensional network and stack the molecules along the b axis.

Related literature

For biological applications of 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006 ▶); Kumar et al. (2012 ▶); Oruç et al. (2004 ▶); Kadi et al. (2007 ▶); Noolvi et al. (2011 ▶); Matysiak et al. (2006 ▶); Marganakop et al. (2012 ▶). For a related structure, see: Zhang (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-69-0o701-scheme1.jpg

Experimental

Crystal data

C₁₂H₁₂FN₃O₂S
M _r = 281.31
Monoclinic,
a = 9.5061 (6) Å
b = 11.2152 (7) Å
c = 12.7752 (7) Å
β = 101.823 (4)°
V = 1333.11 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.770, T _max = 1.000
11372 measured reflections
2352 independent reflections
2035 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.121
S = 1.07
2352 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(21.9KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009367/sj5314sup1.cif

e-69-0o701-sup1.cif^{(21.9KB, cif)}

Click here for additional data file.^{(113.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009367/sj5314Isup2.hkl

e-69-0o701-Isup2.hkl^{(113.2KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813009367/sj5314Isup3.cml

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
N5—H5⋯O4ⁱ	0.86	1.96	2.815 (2)	171
C10—H10⋯O3ⁱⁱ	0.93	2.58	3.267 (3)	131
C17—H17A⋯O4ⁱ	0.96	2.46	3.316 (3)	148
C19—H19B⋯O4ⁱⁱⁱ	0.96	2.55	3.335 (3)	139

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

Acknowledgments

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives are of great importance to chemists as well as biologists as they are found in a large variety of naturally occurring compounds and also pharmacologically potent molecules. These derivatives are known to exhibit a broad spectrum of activities including antiproliferative, antituberculosis, anti-inflammatory, anticancer and antimicrobial activities (Matysiak et al., 2006; Kumar et al., 2012; Oruç et al., 2004; Kadi et al., 2007; Noolvi et al., 2011; Matysiak & Opolski, 2006; Marganakop et al., 2012).

The asymmetric unit of the structure of N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl] -acetamide is shown in Fig. 1 and exhibits a short intramolecular S2···O3 contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring (S2/N6/N7/C14/C15) and the benzene ring (C8–C13) is 86.82 (11)°. In the structure, all bond lengths and angles are within normal ranges (Zhang, 2009).

In the crystal, the N5—H5···O4 and C17—H17A···O4 hydrogen bonds (Table 1) link adjacent molecules forming rings with an R¹₂(6) graph-set motif (Bernstein et al., 1995). The crystal structure is further stabilized by other intermolecular C—H···O hydrogen bonds, (Table 1), that generate inversion dimers with R²₂(8) ring motifs. The overall crystal packing components generate a three-dimensional network, stacking molecules along the b axis, (Fig. 2).

Experimental

A mixture of p-fluorobenzaldehyde (0.005 mole), and thiosemicarbazide (0.005 mole) was refluxed in ethanol (10 ml) and acetic acid (2 drops), after completion of the reaction the resulting pale yellow powder was filtered, dried and crystallized in ethanol to obtain (E)-1-(4-fluoro benzylidene)thiosemicarbazide, which was further heated at 80–90°C for about 4 hrs and the reaction mixture was cooled to room temperature and poured into ice cold water. The precipitate obtained was filtered off, washed with water, dried and purified by crystallization in aqueous alcohol (80%, v/v) to yield pale yellow crystals of N– [4-acetyl-5-(4-fluorophenyl)-4,5-dihydro-[1,3,4]thiadiazol-2-yl]- acetamide. Yield: (70%), m. p: 490 K.