N-(3,5-Dichloro­phen­yl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun; Ching Kheng Quah; B Narayana; Prakash S Nayak; B K Sarojini

doi:10.1107/S1600536811041468

. 2011 Oct 12;67(Pt 11):o2941–o2942. doi: 10.1107/S1600536811041468

N-(3,5-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, B Narayana ^b, Prakash S Nayak ^b, B K Sarojini ^c

PMCID: PMC3247353 PMID: 22219971

Abstract

In the title compound, C₁₈H₁₃Cl₂NO, the naphthalene ring system [maximum deviation = 0.038 (4) Å] and the benzene ring form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the essentially planar acetamide unit [maximum deviation = 0.004 (4) Å]. The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring. In the crystal, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming chains along [001].

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 related structures, see: Fun et al. (2010 ▶, 2011 ▶); Li & Wu (2010 ▶); Xiao et al. (2010 ▶); Praveen et al. (2011 ▶); Wang et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₃Cl₂NO
M _r = 330.19
Monoclinic,
a = 7.8090 (14) Å
b = 24.811 (4) Å
c = 9.6783 (13) Å
β = 125.05 (1)°
V = 1535.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.38 × 0.29 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.855, T _max = 0.974
16035 measured reflections
4453 independent reflections
2621 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.198
S = 1.03
4453 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.33 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/S1600536811041468/lh5351sup1.cif

e-67-o2941-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041468/lh5351Isup2.hkl

e-67-o2941-Isup2.hkl^{(218.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041468/lh5351Isup3.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
N1—H1N1⋯O1ⁱ	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC-New Delhi, Government of India, for financial assistance for the purchase of chemicals through a BSR one-time grant.

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 & Marinkovic, 2006; Mijin et al., 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., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al., 2010), N-benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy) acetamide (Li & Wu, 2010) and N-(3-chloro-4-fluorophenyl)-2- (naphthalen-1-yl)acetamide (Praveen et al., 2011)have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2010, 2011; Wang et al., 2010). The naphthalene ring system (C9-C18, maximum deviation of 0.038 (4) Å at atom C9) and the benzene ring (C1-C6) form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the acetamide moiety (O1/N1/C7/C8, maximum deviation of 0.004 (4) Å at atom C7). The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring.

In the crystal, (Fig. 2), molecules are linked via intermolecular N1–H1N1···O1ⁱ hydrogen bonds (Table 1) to form one-dimensional chains along [001].

Experimental

Naphthalen-1-acetic acid (0.186g, 1 mmol) and 3,5-dichloroaniline (0.162g, 1 mmol) 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, and was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from toluene and acetone mixture by the slow evaporation method (m.p.: 422-425 K).