N-(4-Chloro-1,3-benzothia­zol-2-yl)-2-(3-methyl­phen­yl)acetamide monohydrate

A S Praveen; Jerry P Jasinski; James A Golen; H S Yathirajan; B Narayana

doi:10.1107/S1600536811035872

. 2011 Sep 14;67(Pt 10):o2602–o2603. doi: 10.1107/S1600536811035872

N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate

A S Praveen ^a, Jerry P Jasinski ^b,^*, James A Golen ^b, H S Yathirajan ^a, B Narayana ^c

PMCID: PMC3201351 PMID: 22064942

Abstract

In the title compound, C₁₆H₁₃ClN₂OS·H₂O, the dihedral angle between the mean planes of the benzothiazole ring system and the methylphenyl ring is 79.3 (6)°. The crystal packing features intermolecular O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds involving the water molecule and weak C—H⋯O, C—H⋯Cg and π–π stacking interactions [centroid–centroid distances = 3.8743 (7), 3.7229 (7) and 3.7076 (8) Å].

Related literature

For the biological activity of compounds with benzothiazole skeletons, see: Aiello et al. (2008 ▶); Cho et al. (2008 ▶). For their structural similarity to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2006 ▶, 2008 ▶) and for their coordination abilities, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Davis & Healy (2010 ▶); John et al. (2010 ▶); Nogueira et al. (2010 ▶); Praveen et al. (2011 ▶); Selig et al. (2010 ▶); Wen et al. (2010 ▶); Xiao et al. (2010 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₃ClN₂OS·H₂O
M _r = 334.81
Triclinic,
a = 7.2771 (3) Å
b = 9.2568 (5) Å
c = 12.0851 (5) Å
α = 83.948 (4)°
β = 84.306 (3)°
γ = 72.133 (4)°
V = 768.58 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 173 K
0.25 × 0.21 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.908, T _max = 0.926
10307 measured reflections
4303 independent reflections
3834 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.089
S = 1.01
4303 reflections
209 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811035872/im2316sup1.cif

e-67-o2602-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035872/im2316Isup2.hkl

e-67-o2602-Isup2.hkl^{(210.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811035872/im2316Isup3.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
O2—H2OB⋯N1ⁱ	0.88 (1)	2.10 (2)	2.924 (1)	158 (2)
O2—H2OA⋯O1ⁱⁱ	0.88 (1)	2.05 (1)	2.904 (1)	164 (2)
N2—H2N⋯O2	0.87 (1)	1.92 (1)	2.785 (1)	177 (2)
C5—H5A⋯O1ⁱⁱⁱ	0.95	2.56	3.351 (2)	141
C3—H3A⋯Cg3^iv	0.95	2.66	3.502 (1)	148

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

Acknowledgments

ASP and HSY thank the UoM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

The biological activity of compounds with benzothiazole skeletons includes anticancer, antibacterial, antifungal and anthelmintic properties (Aiello et al., 2008; Cho et al., 2008) N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2008; Mijin et al., 2006). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008; 2010). Crystal structures of some acetamidederivatives, viz., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al., 2010), N-benzyl-2-(3-chloro-4-hydroxyphenyl)acetamide (Davis et al., 2010), 2-[(5,7-dibromoquinolin-8-yl)oxy]-N-(2-methoxyphenyl)acetamide (Wen et al., 2010), N-(4-bromophenyl)-2-(2-thienyl)acetamide (Nogueira et al., 2010), N-[4-(benzylsulfamoyl)phenyl]acetamide (John et al., 2010), 2-(4-fluorophenyl)-N-{4-[6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3] thiazol-5-yl]pyridin-2-yl}acetamide (Selig et al., 2010) and N-(3-chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011) have been reported. As part of our ongoing studies of amides, the title compound is synthesized and its crystal structure is reported.

In the title hydrated compound, C₁₆H₁₃ClN₂OS × H₂O, the dihedral angle between the mean planes of the benzothiazole and benzenes is 79.3 (6)° (Fig. 1). Crystal packing is realized by O–H···N, O—H···O and N—H···O hydrogen bonds involving the water molecule and weak O—H···O, C—H···O, C—H···Cg (Table 1) and π–π stacking (Table 2) intermolecular interactions (Fig. 2).

Experimental

To a stirred solution of (3-methylphenyl)acetic acid (1 g, 6.65 mmol), triethylamine (1.34 g, 13.31 mmol) and 4-chloro-1,3-benzothiazol-2-amine (1.27 g, 6.65 mmol) in dichloromethane (10 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (1.52 g, 7.93 mmol) was added at 273 K. The reaction mixture was stirred at room temperature for 3 h. After the completion of the reaction, the reaction mixture was poured into ice cold water and the layers were separated. The organic layer was washed with 10% aq. NaHCO₃ solution (10 ml), brine (10 ml), dried over anhydrous Na₂SO₄, filtered and concentrated under vacuum to obtain the crude product which was triturated with ethanol and filtered to afford 1.92 g of the title compound (I) as a white solid in 91 % yield. Single crystals were grown from ethanol by slow evaporation method (m.p.: 397-398 K).