N-(2,6-Dichloro­phen­yl)-2-(naphthalen-1-yl)acetamide

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

doi:10.1107/S1600536812014869

. 2012 Apr 13;68(Pt 5):o1385. doi: 10.1107/S1600536812014869

N-(2,6-Dichlorophenyl)-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: PMC3344513 PMID: 22590275

Abstract

In the title compound, C₁₈H₁₃Cl₂NO, the naphthalene ring system and the benzene ring form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide grouping [maximum deviation = 0.005 (3) Å]. The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010]. The O atom also accepts two C—H⋯O interactions.

Related literature

For related structures, see: Fun et al. (2010 ▶, 2011a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₃Cl₂NO
M _r = 330.19
Monoclinic,
a = 13.1918 (13) Å
b = 4.7199 (5) Å
c = 24.878 (2) Å
β = 103.127 (3)°
V = 1508.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100 K
0.38 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.853, T _max = 0.968
13545 measured reflections
4397 independent reflections
3245 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.168
S = 1.08
4397 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.56 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/S1600536812014869/hb6731sup1.cif

e-68-o1385-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014869/hb6731Isup2.hkl

e-68-o1385-Isup2.hkl^{(215.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014869/hb6731Isup3.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	0.84 (4)	2.00 (4)	2.823 (3)	165 (3)
C8—H8A⋯O1ⁱ	0.99	2.37	3.242 (4)	146
C8—H8B⋯O1ⁱⁱ	0.99	2.53	3.488 (4)	163

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

Acknowledgments

The authors would like to thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the 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 and structures of amides (Fun et al., 2010, 2011a,b) 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,b). The naphthalene ring system (C9-C18, maximum deviation of 0.017 (3) Å at atom C9) and the benzene ring (C1-C6) form dihedral angles of 74.73 (13) and 62.53 (16)°, respectively, with the acetamide moiety (O1/N1/C7/C8, maximum deviation of 0.005 (3) Å at atom C7). The naphthalene ring system forms a dihedral angle of 75.14 (13)° with the benzene ring.

In the crystal, Fig. 2, molecules are linked via N1–H1N1···O1, C8–H8A···O1 and C8–H8B···O1 hydrogen bonds (Table 1) into two-molecule-thick chains along [010].

Experimental

1-Naphthalene acetic acid (0.186 g, 1 mmol) and 2,6-dichloroaniline (0.162 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20ml). 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, which 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. Colourless needles were grown from N,N-dimethyl formamide solution by the slow evaporation method (m.p.: 463K).