2,2-Diphenyl-N-(1,3-thia­zol-2-yl)acetamide

Hoong-Kun Fun; Chin Wei Ooi; Prakash S Nayak; B Narayana; B K Sarojini

doi:10.1107/S1600536812013840

. 2012 Apr 6;68(Pt 5):o1312–o1313. doi: 10.1107/S1600536812013840

2,2-Diphenyl-N-(1,3-thiazol-2-yl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Chin Wei Ooi ^a, Prakash S Nayak ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3344455 PMID: 22590217

Abstract

In the title molecule, C₁₇H₁₄N₂OS, the mean plane of the acetamide group forms dihedral angles of 75.79 (5), 81.85 (6) and 12.32 (5)° with the two phenyl rings and the thiazole ring, respectively. In the crystal, N—H⋯N hydrogen bonds link pairs of molecules into inversion dimers with R ₂ ²(8) ring motifs. The crystal packing is further stabilized by C—H⋯π interactions and by π–π interactions with a centroid–centroid distance of 3.6977 (5) Å.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶,2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶); Fun et al. (2011a ▶,b ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂OS
M _r = 294.36
Monoclinic,
a = 5.6915 (1) Å
b = 15.1889 (2) Å
c = 16.5967 (2) Å
β = 97.845 (1)°
V = 1421.32 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.41 × 0.22 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.912, T _max = 0.967
23915 measured reflections
6275 independent reflections
5255 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.106
S = 1.05
6275 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013840/lh5446sup1.cif

e-68-o1312-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013840/lh5446Isup2.hkl

e-68-o1312-Isup2.hkl^{(307.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013840/lh5446Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2ⁱ	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A⋯Cg2ⁱⁱ	0.95	2.88	3.6647 (11)	141
C12—H12A⋯Cg1ⁱⁱⁱ	0.95	2.92	3.6143 (13)	131
C17—H17A⋯Cg1^iv	0.95	2.61	3.4381 (11)	146

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

Acknowledgments

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

supplementary crystallographic information

Comment

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006;2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008;2010). Crystal structures of some acetamide derivatives viz., N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl) acetamide monohydrate, N-(3-Chloro-4-fluorophenyl)-2,2-diphenylacetamide and N-(3-Chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011a,b,c) have been reported. In continuation of our work on synthesis of amides (Fun et al., 2011 a, b), we report herein the crystal structure of the title compound (I).

In the title compound (Fig. 1), the mean plane of acetamide (O1/N1/C7/C14) group makes dihedral angles of 75.79 (5)°, 81.85 (6)° and 12.32 (5)° with the two terminal phenyl rings (C1–C6 & C8–C13) and thiazole (S1/N2/C15–C17) ring, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Praveen et al., 2011a,b,c; Fun et al., 2011a,b).

In the crystal (Fig. 2), intermolecular N1—H1N1···N26ⁱ hydrogen bonds (Table 1) link molecules to form R₂² (8) ring motifs (Bernstein et al., 1995), leading to the formation of dimers. The crystal packing is further stabilized by C—H···π interactions, involving the C1–C6 ring (centroid Cg1) and C8–C13 ring (centroid Cg2). Weak π–π interactions are observed with Cg3···Cg3 = 3.6977 (5) Å [symmetry code: 2-x, 1-y, 1-z], where Cg3 is the centroid of thiazole ring (S1/N2/C15–C17).

Experimental

Diphenylacetic acid (0.212 g, 1 mmol), 2-amino thiazole (0.1 g, 1 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The resultant mixture was then extracted three times with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methylene chloride and methanol (1:1) mixture by the slow evaporation method. (M.P.: 409–411 K).