(Z)-N-[3-(2-Methoxy­phen­yl)-4-phenyl-2,3-dihydro­thia­zol-2-yl­idene]-2-methyl­benzamide

Aamer Saeed; Sabah Zaman; Ulrich Flörke

doi:10.1107/S1600536807062290

. 2007 Dec 6;64(Pt 1):o66. doi: 10.1107/S1600536807062290

(Z)-N-[3-(2-Methoxyphenyl)-4-phenyl-2,3-dihydrothiazol-2-ylidene]-2-methylbenzamide

Aamer Saeed ^a,^*, Sabah Zaman ^a, Ulrich Flörke ^b

PMCID: PMC2915024 PMID: 21200943

Abstract

In the title molecule, C₂₄H₂₀N₂O₂S, the thiazole and amide groups are essentially coplanar. The thiazole ring forms dihedral angles of 61.62 (4) and 26.75 (5)° with the benzene rings of the methoxyphenyl and methylphenyl groups, respectively, and 33.69 (6)° with the phenyl ring. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Arcadi et al. (2003 ▶); Bonde & Gaikwad (2004 ▶); Kim et al. (2007 ▶); Lee & Sim (2000 ▶); Saeed & Parvez (2006 ▶); Shehata et al. (1996 ▶); Venkatachalan et al. (2001 ▶).

Experimental

Crystal data

C₂₄H₂₀N₂O₂S
M _r = 400.48
Monoclinic,
a = 9.7826 (18) Å
b = 15.010 (3) Å
c = 13.917 (3) Å
β = 105.092 (4)°
V = 1973.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 153 (2) K
0.50 × 0.40 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.912, T _max = 0.955
16940 measured reflections
4697 independent reflections
4150 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.102
S = 1.04
4697 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062290/lh2546sup1.cif

e-64-00o66-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062290/lh2546Isup2.hkl

e-64-00o66-Isup2.hkl^{(230.1KB, 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
C3—H3A⋯N1	0.95	2.42	2.7572 (18)	101
C14—H14A⋯O1ⁱ	0.95	2.52	3.4635 (19)	171
C22—H22A⋯O1ⁱⁱ	0.95	2.48	3.4240 (18)	170

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

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

supplementary crystallographic information

Comment

2-Imino derivatives of 1,3-thiazolines posses a wide range of pharmacological and synthetic applications. Thus, these show potent bioactivities ranging from antitubercular (Shehata et al., 1996) to anti-HIV (Venkatachalan et al., 2001) activities. Iminothiazolines containing a pyrazine ring show significant antibacterial and antimicrobial activity (Bonde & Gaikwad 2004), derivatives of rhodanine show antibacterial, anti-inflammatory and antiviral activities (Lee & Sim et al., 2000) and bis-thiazoline derivatives show marked anti-cancer activity against human cell lines (Arcadi et al., 2003). A 2-imino-1,3-thiazoline derivative KHG22394 acts as a skin whitening agent (Kim et al., 2007).

Experimental

The title compound was prepared according to the method reported earlier (Saeed & Parvez 2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Full spectroscopic and physical characterization will be reported elsewhere.