N-(3-Chloro-4-fluoro­phen­yl)-2,2-diphenyl­acetamide

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

doi:10.1107/S1600536811036075

. 2011 Sep 14;67(Pt 10):o2604. doi: 10.1107/S1600536811036075

N-(3-Chloro-4-fluorophenyl)-2,2-diphenylacetamide

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

PMCID: PMC3201262 PMID: 22058752

Abstract

In the title compound, C₂₀H₁₅ClFNO, the dihedral angles between the mean planes of the acetamide group and the chlorofluoro-substituted benzene ring and the two phenyl rings are 10.8 (8), 81.9 (7) and 85.8 (5)°, respectively. The crystal packing is stabilized by N—H⋯O hydrogen bonds and weak C—H⋯O intermolecular interactions, forming infinite chains along the c 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 their coordination abilities, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Davis & Healy (2010 ▶); Li et al. (2010 ▶); Li & Wu (2010 ▶); Wang et al. (2010 ▶); Xiao et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₁₅ClFNO
M _r = 339.78
Monoclinic,
a = 9.3665 (17) Å
b = 10.2069 (12) Å
c = 9.7774 (16) Å
β = 114.42 (2)°
V = 851.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.35 × 0.12 × 0.12 mm

Data collection

Oxford Diffractio Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.921, T _max = 0.972
7456 measured reflections
3794 independent reflections
3265 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.109
S = 1.01
3794 reflections
220 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ▶), 1668 Friedel pairs
Flack parameter: −0.06 (6)

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) I. DOI: 10.1107/S1600536811036075/ya2145sup1.cif

e-67-o2604-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036075/ya2145Isup2.hkl

e-67-o2604-Isup2.hkl^{(186KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036075/ya2145Isup3.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
C1—H1A⋯O1ⁱ	0.95	2.49	3.256 (3)	138
N1—H1N⋯O1ⁱ	0.85 (2)	2.09 (2)	2.895 (2)	158 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

ASP thanks 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

Amides are extensively used as ligands due to their excellent coordination abilities (Wu et al., 2008; 2010). N-Substituted 2-arylacetamides are especially remarkable due to their structural similarity to the lateral chain of natural benzylpenicillin (Mijin & Marinkovic, 2006; Mijin et al., 2008). Crystal structures of some acetamide derivatives, viz., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al., 2010), N-benzyl-2-(3-chloro-4-hydroxyphenyl)acetamide (Davis & Healy, 2010), 2-(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yloxy)-N- (o-tolyl)acetamide (Li et al., 2010), N-benzyl-2-(2-bromophenyl)-2- (2-nitrophenoxy)acetamide (Li & Wu, 2010) and N-(4-chlorophenyl)-2-(8-quinolyloxy)acetamide monohydrate (Wang et al., 2010) have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound, C₂₀H₁₅ClFNO.

In the title compound, the dihedral angles between the mean planes of the acetamide group 01/N1/C6/C7/C8 and the chloro, fluoro substituted benzene ring C1-C6 and two phenyl rings C9-C14 and C15-C20 are 10.8 (8)°, 81.9 (7)° and 85.8 (5)°, respectively (Fig. 2). Crystal packing is stabilized by N1—H1N···O1ⁱ hydrogen bonds and weak C1—H1A···O1ⁱ (symmetry code i: x, 1-y, z+1/2) intermolecular interactions forming infinite one-dimensional chains along the c axis (Fig. 3, Table 1).

Experimental

Diphenylacetyl chloride (0.230 g, 1 mmol) and 3-chloro-4-fluoroaniline (0.145 g, 1 mmol) were dissolved in dichloromethane (20 mL). The mixture was stirred in the presence of triethylamine at 273 K for about 3 h (Fig. 1). The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted three times with dichloromethane. The organic layer was washed with saturated NaHCO₃ and brine solutions, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from toluene by the slow evaporation method (M.P.: 427 K).