2,2-Diphenyl­acetamide

Jerry P Jasinski; James A Golen; M S Siddegowda; H S Yathirajan; M T Swamy

doi:10.1107/S1600536811026717

. 2011 Jul 9;67(Pt 8):o1992–o1993. doi: 10.1107/S1600536811026717

2,2-Diphenylacetamide

Jerry P Jasinski ^a,^*, James A Golen ^a, M S Siddegowda ^b, H S Yathirajan ^b, M T Swamy ^c

PMCID: PMC3213448 PMID: 22091027

Abstract

In the title compound, C₁₄H₁₃NO, which has two molecules in the asymmetric unit, the dihedral angles between the mean planes of the benzene rings are 84.6 (7) and 85.0 (6)°. N—H⋯O hydrogen bonds [forming R ₂ ²(8) ring motifs] and C—H⋯O hydrogen bonds dominate the crystal packing, forming zigzag chains parallel to the a axis. In addition, weak intermolecular C—H⋯π interactions are observed.

Related literature

For the synthesis and antimycobacterial activity of 2,2-diphenylacetamide derivatives, see: Guzel et al. (2006 ▶). For related structures, see: Akkurt et al. (2007 ▶); Dutkiewicz et al. (2010 ▶); Gerkin (1998 ▶); Krigbaum et al. (1968 ▶); Narasegowda et al. (2005 ▶); Yathirajan et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₃NO
M _r = 211.25
Monoclinic,
a = 5.1687 (3) Å
b = 28.5511 (13) Å
c = 7.8006 (4) Å
β = 98.152 (5)°
V = 1139.52 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 173 K
0.40 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.792, T _max = 0.887
6490 measured reflections
3978 independent reflections
3869 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.107
S = 1.07
3978 reflections
303 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) global, I. DOI: 10.1107/S1600536811026717/jh2307sup1.cif

e-67-o1992-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026717/jh2307Isup2.hkl

e-67-o1992-Isup2.hkl^{(195KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026717/jh2307Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1ⁱ	0.89 (1)	2.20 (2)	2.9409 (17)	140 (2)
N1—H1A⋯O2ⁱⁱ	0.87 (1)	2.09 (1)	2.9575 (19)	177 (2)
N2—H2B⋯O1ⁱⁱⁱ	0.88 (1)	2.07 (1)	2.9526 (19)	176 (2)
N2—H2A⋯O2^iv	0.89 (1)	2.17 (2)	2.9407 (18)	145 (2)
N1—H1A⋯N2ⁱⁱ	0.87 (1)	3.06 (2)	3.7246 (18)	134 (2)
N2—H2B⋯N1ⁱⁱⁱ	0.88 (1)	3.10 (2)	3.7246 (18)	130 (2)
C10—H10A⋯O1	0.95	2.50	3.093 (2)	120
C18—H18A⋯O2	0.95	2.51	3.099 (2)	120
C2—H2C⋯Cg1ⁱ	1.00	2.96	3.9379 (18)	165
C16—H16A⋯Cg4^iv	1.00	2.95	3.9263 (18)	166

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

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer. MSS thanks the University of Mysore for the research facilities and R. L. Fine Chem, Bangalore, India, for the gift sample.

supplementary crystallographic information

Comment

The synthesis and antimycobacterial activity of some new 2,2-diphenylacetamide derivatives is described (Guzel et al., 2006). The title compound is used to synthesize various biologically active and pharmaceutical compounds viz., loperamide, darifenacin, fenpiverine, etc. The crystal structures of N,N-diphenylacetamide (Krigbaum et al., 1968), 4,4'-dimethylbiphenyl-2,2'-dicarboxylic acid (Gerkin, 1998), 4'-methylbiphenyl-2-carboxylic acid (Narasegowda et al., 2005) and 4'-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)biphenyl-2-carbonitrile (Yathirajan et al., 2005), 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide (Akkurt et al., 2007) and 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide (Dutkiewicz et al., 2010) have been reported. In view of the importance of the title compound, (I), C₁₄H₁₃NO, and in order to determine the conformation of this molecule, a crystal structure determination has been carried out.

In the title compound, (I), with two molecules in the asymmetric unit, the dihedral angle between the mean planes of the benzene rings is 84.6 (7)° or 85.0 (6)°, respectively (Fig. 1). Extensive N—H···O (forming an R₂²(8) ring-motif) intermolecular and C—H···O intramolecular hydrogen bonds and weak C—H···Cg π-ring intermolecular interactions (dominate the crystal packing forming a zigzag chain along [010] (Table 1, Fg. 2).

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of 1:1 acetone:methanol solution (m.p.: 430-433 K).