N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-2-eth­oxy­benzamide

S Naveen; Basappa; H R Manjunath; M A Sridhar; J Shashidhara Prasad; K S Rangappa

doi:10.1107/S1600536810019811

. 2010 Jun 5;66(Pt 7):o1533. doi: 10.1107/S1600536810019811

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-ethoxybenzamide

S Naveen ^a, Basappa ^b, H R Manjunath ^c, M A Sridhar ^c,^*, J Shashidhara Prasad ^c, K S Rangappa ^b

PMCID: PMC3006830 PMID: 21587782

Abstract

In the title compound, C₁₇H₁₃F₃N₂O₂, the two aromatic rings are essentially coplanar, forming a dihedral angle of 2.78 (12)°. The non-H atoms of the ethoxy group are coplanar with the attached ring [maximum deviation = 0.271 (3) Å]. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, molecules are linked by intermolecular C—H⋯N and C—H⋯F hydrogen bonds.

Related literature

For background to the biological activity of ethoxybenzamides, see: Mantelingu et al. (2007 ▶). For related structures, see: Ma et al. (2009 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₃F₃N₂O₂
M _r = 334.29
Monoclinic,
a = 10.5010 (13) Å
b = 12.8830 (16) Å
c = 11.6130 (14) Å
β = 101.653 (6)°
V = 1538.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.32 × 0.30 × 0.27 mm

Data collection

MacScience DIPLabo 32001 diffractometer
5043 measured reflections
2704 independent reflections
1896 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.176
S = 1.02
2704 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019811/wn2389sup1.cif

e-66-o1533-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019811/wn2389Isup2.hkl

e-66-o1533-Isup2.hkl^{(132.8KB, hkl)}

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
N7—H1⋯O15	0.96	1.82	2.661 (2)	145
C1—H16⋯N19ⁱ	0.96	2.47	3.377 (3)	157
C13—H18⋯F23ⁱⁱ	0.96	2.50	3.365 (3)	150

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

Acknowledgments

The authors are grateful to the DST and Government of India project SP/I2/FOO/93, also the University of Mysore, Mysore for financial assistance. HRM thanks the UGC-BRS and the University of Mysore for the award of a fellowship.

supplementary crystallographic information

Comment

Histone acetyl transfereses (HAT) are enzymes that acetylate conserved lysine amino acids on histone proteins by transferring the acetyl group from acetyl CoA to form ε-N-acetyl lysine. HAT functions to promote transcriptional activation and has significant histone acetyl transferase activity with core histones (H3 and H4), and also with nucleosome core particles. In addition, HAT inhibits cell-cycle progression and counteracts the mitogenic activity of the adenoviral oncoprotein E1A. A literature survey revealed that the small molecule KCN weakly activated the p300 histone acetyl transferase (Mantelingu et al. 2007). With this background, the title compound was synthesized and we report its crystal structure here.

A perspective view of the title compound is shown in Fig. 1. The bond lengths and bond angles are normal and are comparable with values reported earlier for N-(3,4-diethoxyphenyl)acetamide (Ma et al. 2009). The dihedral angle between the two aromatic rings is 2.78 (12)°, indicating that the two aromatic rings are essentially coplanar. This value differs from the value of 55.69 (3)° reported earlier (Saeed et al. 2010). The carbamide group connecting the two rings is -anti-periplanar, as indicated by the torsion angle value of -177.2 (2)° for C5—N7—C8—C9. The non-H atoms of the ethoxy group lie within the plane of the aromatic ring, as confirmed by the torsion angle value of 174.3 (2)° for C14—O15—C16—C17. In the crystal structure, the molecules exhibit both intramolecular N—H···O and intermolecular hydrogen bonds of the type C—H···N and C—H···F. The molecules exhibit layered stacking when viewed down the b axis, as shown in Fig. 2.

Experimental

N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-ethoxybenzamide was synthesized according to the procedure reported earlier (Mantelingu et al. 2007). The final product was obtained by crystallization using methanol as solvent. Slow evaporation of the solvent yielded colorless crystals after three days.