4-Fluoro-N-[3-(2-fluoro­phen­yl)-4-methyl-2,3-dihydro-2-thienyl­idene]benzamide

Aamer Saeed; Uzma Shaheen; Muhammad Latif; Michael Bolte

doi:10.1107/S1600536809022314

. 2009 Jun 20;65(Pt 7):o1643. doi: 10.1107/S1600536809022314

4-Fluoro-N-[3-(2-fluorophenyl)-4-methyl-2,3-dihydro-2-thienylidene]benzamide

Aamer Saeed ^a,^*, Uzma Shaheen ^a, Muhammad Latif ^b, Michael Bolte ^c

PMCID: PMC2969331 PMID: 21582907

Abstract

In the title compound, C₁₇H₁₂F₂N₂OS, the planar thiazole ring (r.m.s. deviation = 0.012 Å) makes dihedral angles of 15.08 (9) and 81.81 (6)° with the 4-fluorophenyl and 2-fluorophenyl rings, respectively. The 2-fluorophenyl ring is disordered over two orientations with site-occupancy factors of 0.810 (3) and 0.190 (3). The structure contains intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of imino-1,3-thiazoline derivatives, see: Kim et al. (2007 ▶); Vicini et al. (2006 ▶); Hosseinimehr et al. (2001 ▶); Zhang et al. (2000 ▶); Pietrancosta et al. (2006 ▶). For details of the synthesis, see: Saeed et al. (2008a ▶). For a related structure, see: Saeed et al. (2008b ▶).

Experimental

Crystal data

C₁₇H₁₂F₂N₂OS
M _r = 330.35
Orthorhombic,
a = 7.0982 (14) Å
b = 11.423 (2) Å
c = 18.949 (4) Å
V = 1536.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.36 × 0.34 × 0.28 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T _min = 0.920, T _max = 0.937
10484 measured reflections
3531 independent reflections
3213 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.082
S = 0.99
3531 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 1491 Friedel pairs
Flack parameter: −0.15 (6)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022314/bi2375sup1.cif

e-65-o1643-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022314/bi2375Isup2.hkl

e-65-o1643-Isup2.hkl^{(173.2KB, 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
C5—H5⋯O1ⁱ	0.95	2.41	3.322 (2)	160

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The imino-1,3-thiazoline group is found in a variety of biologically active natural products and finds extensive applications in medicinal chemistry. 2-Thiazolylimino-5-arylidene-4-thiazolidinones show noticeable antimicrobial activity against bacteria, yeasts and mould (Kim et al., 2007). 3-Substituted 2-(cyanoimino)thiazolidines can be used in agriculture due to their neonicotinoid insecticidal activity (Vicini et al., 2006). 3-Substituted thiazolidines show radioprotective properties against γ-radiation (Hosseinimehr et al., 2001). KHG22394, a 2-imino-1,3-thiazoline derivative, significantly inhibits melanin production in a dose-dependent manner, thus acting as a skin whitening agent (Zhang et al., 2000) and pifithrin-alpha, another iminothiazoline, is a reversible inhibitor of p53-mediated apoptosis and p53-dependent gene transcription (Pietrancosta et al., 2006).

Experimental

The title compound was prepared according to the procedure reported earlier (Saeed et al. (2008a). Crystallization of the residue in CHCl₃ afforded the title compound (81%) as white needles: Anal. calcd. for C₁₄H₁₂Cl_NO1: C 68.44, H 4.92, N 5.70%; found: C 68.39, H 4.90, N 5.67%