N-(1,3-Benzo­thia­zol-2-yl)acetamide

Prakash S Nayak; B Narayana; Jerry P Jasinski; H S Yathirajan; Manpreet Kaur

doi:10.1107/S160053681302730X

. 2013 Oct 9;69(Pt 11):o1622. doi: 10.1107/S160053681302730X

N-(1,3-Benzothiazol-2-yl)acetamide

Prakash S Nayak ^a, B Narayana ^a, Jerry P Jasinski ^b,^*, H S Yathirajan ^c, Manpreet Kaur ^c

PMCID: PMC3884296 PMID: 24454072

Abstract

The title compound, C₉H₈N₂OS, crystallizes with two molecules (A and B) in the asymmetric unit. The dihedral angles between the mean planes of the 1,3-benzothiazol-2-yl ring system and the acetamide group are 2.7 (4) (molecule A) and 7.2 (2) Å (molecule B). In the crystal, pairs of N—H⋯N hydrogen bonds link the A and B molecules into dimers, generating R ₂ ²(8) loops. The dimers stack along [100].

Related literature

For the related crystal structure of the acetamide derivatives, see: Jasinski et al. (2013 ▶); Fun et al. (2011a ▶,b ▶, 2012 ▶). graphic file with name e-69-o1622-scheme1.jpg

Experimental

Crystal data

C₉H₈N₂OS
M _r = 192.24
Monoclinic,
a = 11.1852 (4) Å
b = 7.4037 (4) Å
c = 20.9189 (8) Å
β = 94.408 (3)°
V = 1727.21 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 173 K
0.45 × 0.24 × 0.15 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶)T _min = 0.770, T _max = 1.000
20845 measured reflections
5918 independent reflections
4622 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.109
S = 1.08
5918 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302730X/hb7144sup1.cif

e-69-o1622-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302730X/hb7144Isup2.hkl

e-69-o1622-Isup2.hkl^{(324.3KB, hkl)}

Click here for additional data file.^{(3.6KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681302730X/hb7144Isup3.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
N2A—H2A⋯N1B	0.86	2.11	2.9700 (16)	176
N2B—H2B⋯N1A	0.86	2.14	2.9749 (16)	165

Open in a new tab

Acknowledgments

BN thanks the UGC for financial assistance through BSR one time grant for the purchase of chemicals and DST–PURSE for financial assistance. HSY thanks University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

1. Comment

In continuation of our work on the synthesis of acetamide derivatives (Jasinski et al. 2013), we report herein the crystal structure of the title compound, C₉H₈N₂OS, (I). Some of the related crystal structures of similar acetamide derivatives include, N-(3-chloro-4-fluorophenyl)acetamide, N-(4-bromophenyl)-2-(naphthalen-1- yl)acetamide and N-(3,5-dichlorophenyl)-2-(naphthalen-1-yl)acetamide (Fun et al. 2011a,b, 2012).

The title compound, (I) crystallizes with two independent molecules (A & B) in the asymmetric unit (Fig.1). The dihedral angle between the mean planes of the 1,3-benzothiazol-2-yl ring and the acetamide group is 2.7 (4)° (A) and 7.2 (2)Å (B),(Fig. 2). In the crystal, N—H···N hydrogen bonds forming R₂²(8) graph set motifs which link the molecules into dimers, which stack along [100].

2. Experimental

2-Aminobenzothiazole (1 mmol) were dissolved in a 30 ml acetic acid and it was refluxed for 3 hrs (Fig.3). The reaction mixture was cooled and poured into ice cold water. The precipitate obtained was obtained by filtration and recrystallized in ethanol. Colorless blocks were grown from methanol solution by the slow evaporation method and was used as such for X-ray studies (M.P.: 453-455 K).