2,2-Diphenyl-N-(2,4,5-trichloro­phen­yl)acetamide

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

doi:10.1107/S160053681203440X

. 2012 Aug 8;68(Pt 9):o2659–o2660. doi: 10.1107/S160053681203440X

2,2-Diphenyl-N-(2,4,5-trichlorophenyl)acetamide

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

PMCID: PMC3435685 PMID: 22969556

Abstract

The asymmetric unit of the title compound, C₂₀H₁₄Cl₃NO, consists of two independent molecules. In one molecule, the chlorinated benzene ring forms dihedral angles of 12.00 (9) and 77.04 (9)° with the phenyl rings. The dihedral angle between the phenyl rings is 80.37 (10)°. The corresponding dihedral angles for the other molecule are 26.34 (10), 62.98 (10) and 88.47 (11)°, respectively. One of the molecules features an intramolecular C—H⋯O hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into [100] chains. The chains are further linked by C—H⋯O and C—H⋯Cl hydrogen bonds into a three-dimensional network.

Related literature

For general background to and related structures of the title compound, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). 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

C₂₀H₁₄Cl₃NO
M _r = 390.67
Orthorhombic,
a = 18.6630 (16) Å
b = 17.1713 (15) Å
c = 22.5648 (19) Å
V = 7231.3 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 100 K
0.38 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.830, T _max = 0.946
45180 measured reflections
10676 independent reflections
7536 reflections with I > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.114
S = 1.02
10676 reflections
459 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.49 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/S160053681203440X/hb6924sup1.cif

e-68-o2659-sup1.cif^{(40.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203440X/hb6924Isup2.hkl

e-68-o2659-Isup2.hkl^{(522.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681203440X/hb6924Isup3.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
N1A—H1NA⋯O1B ⁱ	0.78 (2)	2.09 (2)	2.8379 (19)	161 (2)
N1B—H1NB⋯O1A	0.84 (2)	1.94 (2)	2.7684 (19)	168 (2)
C7A—H7AA⋯O1B ⁱ	1.00	2.33	3.234 (2)	151
C1B—H1BA⋯O1B	0.95	2.48	3.116 (3)	125
C3B—H3BA⋯O1B ⁱⁱ	0.95	2.42	3.368 (3)	172
C12B—H12B⋯Cl2B ⁱⁱⁱ	0.95	2.82	3.641 (3)	145
C7B—H7BA⋯O1A	1.00	2.46	3.341 (2)	147

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

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., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, the benzene ring (C15A-C20A) forms dihedral angles of 12.00 (9) and 77.04 (9)° with two phenyl rings (C1A-C6A and C8A-C13A). The dihedral angle between two phenyl rings is 80.37 (10)°. The corresponding dihedral angles for molecule B are 26.34 (10), 62.98 (10) and 88.47 (11)°, respectively. Bond lengths and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a, 2011b, 2012a, 2012b). The molecular structure is stabilized by intramolecular C1B–H1BA···O1B hydrogen bond, forming an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure, Fig. 2, molecules are linked by N1A–H1NA···O1B, N1B–H1NB···O1A, C7A–H7AA···O1B, C3B–H3BA···O1B, C12B–H12B···Cl2B and C7B–H7BA···O1A hydrogen bonds (Table 1) into a three-dimensional network.

Experimental

Diphenylacetic acid (0.212 g, 1 mmol), 2,4,5-trichloroaniline (0.196 g, 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 the 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 concoction was 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 (I). Colourless needles were grown from ethanol solution by the slow evaporation method (m.p.: 391-393K).