N-(4-Bromo­phen­yl)-2-(naphthalen-1-yl)acetamide

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

doi:10.1107/S1600536811041110

. 2011 Oct 12;67(Pt 11):o2926–o2927. doi: 10.1107/S1600536811041110

N-(4-Bromophenyl)-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: PMC3247340 PMID: 22219958

Abstract

In the title compound, C₁₈H₁₄BrNO, the naphthalene ring system and the benzene ring form dihedral angles of 78.8 (2) and 19.7 (2)°, respectively, with the acetamide C—C(=O)—N plane. The naphthalene ring system forms a dihedral angle of 64.88 (19)° with the benzene ring. In the crystal, molecules are linked via intermolecular bifurcated (N,C)—H⋯O hydrogen bonds, generating an R ₂ ¹(6) ring motif, forming chains along the b axis.

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 studies of amides in therapy, myocardial infarction and ischemic disease, see: Dorsch et al. (2002 ▶); Wang, Li & Li (2010 ▶); Wang, Beck et al. (2010 ▶). For related structures, see: Fun et al. (2010 ▶); Li & Wu (2010 ▶); Xiao et al. (2010 ▶); Praveen et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the definition of graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₄BrNO
M _r = 340.21
Orthorhombic,
a = 12.6837 (11) Å
b = 9.4047 (11) Å
c = 25.641 (3) Å
V = 3058.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.415, T _max = 0.523
18691 measured reflections
2999 independent reflections
1864 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.182
S = 1.02
2999 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.53 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/S1600536811041110/is2786sup1.cif

e-67-o2926-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041110/is2786Isup2.hkl

e-67-o2926-Isup2.hkl^{(147.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041110/is2786Isup3.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	2.09	2.879 (3)	167
C11—H11A⋯O1ⁱ	0.97	2.59	3.422 (4)	143

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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) and for the therapy of thromboembolic disorder and effective anticoagulants for myocardial infarction and ischemic disease (Dorsch et al., 2002; Wang, Li & Li, 2010; Wang, Beck et al., 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 a related structure (Fun et al., 2010). The naphthalene ring system (C1–C10, maximum deviation of 0.022 (7) Å at atom C7) and the benzene ring (C13–C18) form dihedral angles of 78.8 (2) and 19.7 (2)°, respectively, with the acetamide moiety [O1/N1/C11/C12, maximum deviation of 0.014 (4) Å at atom C12]. The naphthalene ring system also forms dihedral angle of 64.88 (19)° with the benzene ring.

In the crystal packing (Fig. 2), molecules are linked via intermolecular bifurcated N1—H1N1···O1 and C11—H11A···O1 acceptor bonds (Table 1), generating an R₂¹(6) ring motif, (Bernstein et al., 1995) to form one-dimensional chains along the [010] direction.

Experimental

Naphthalen-1-acetic acid (0.186g, 1 mmol) and 4-bromoaniline (0.172g, 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.: 476-478 K).