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

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

doi:10.1107/S1600536812034423

. 2012 Aug 8;68(Pt 9):o2657. doi: 10.1107/S1600536812034423

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

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

PMCID: PMC3435683 PMID: 22969554

Abstract

In the title compound, C₁₈H₁₄BrNO, the naphthalene ring system [maximum deviation = 0.015 (3) Å] forms a dihedral angle of 67.70 (10)° with the benzene ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into C(4) chains propagating in [100]. A C—H⋯O interaction reinforces the chain connectivity, generating an R ₂ ¹(6) loop.

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2010 ▶, 2011a ▶,b ▶, 2012 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₄BrNO
M _r = 340.21
Orthorhombic,
a = 4.7603 (1) Å
b = 11.4614 (3) Å
c = 26.6255 (6) Å
V = 1452.68 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 100 K
0.32 × 0.16 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.463, T _max = 0.719
16642 measured reflections
3864 independent reflections
3516 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.061
S = 1.03
3864 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ▶), 1587 Friedel pairs
Flack parameter: 0.001 (8)

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/S1600536812034423/hb6923sup1.cif

e-68-o2657-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034423/hb6923Isup2.hkl

e-68-o2657-Isup2.hkl^{(189.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034423/hb6923Isup3.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	0.86 (3)	2.03 (3)	2.855 (3)	163 (2)
C11—H11A⋯O1ⁱ	0.99	2.55	3.279 (3)	130

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of amides (Fun et al., 2010, 2011a, 2011b, 2012), we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths are comparable to related structures (Fun et al., 2010, 2011a, 2011b, 2012). The naphthalene ring system (C1-C10, maximum deviation of 0.015 (3) Å at atom C9) forms a dihedral angle of 67.70 (10)° with the benzene ring (C13-C18).

In the crystal structure, Fig. 2, molecules are linked via N1–H1N1···O1 and C11–H11A···O1 hydrogen bonds (Table 1) into one-dimensional [100] chains which contain R₂¹ (6) ring motifs (Bernstein et al., 1995).

Experimental

1-Naphthaleneacetic acid (0.186 g, 1 mmol), 2-bromoaniline (0.1 ml, 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 concotion was then extracted thrice 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. Colourless blocks were grown from toluene solution by the slow evaporation method (m.p.: 421K).