Acta Crystallographica Section E: Crystallographic Communications

Acta Crystallogr E Crystallogr Commun. 71(Pt 3): o214-o215

Crystal structure of 2-benzamido-N-(2,2-diethoxyethyl)benzamide

Abdelaaziz Ouahroucha, Moha Taourirtea, Hassan B. Lazrekb, Joachim W. Engelsc, Michael Bolted*

a. Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Guéliz (FSTG), BP 549, Marrakech, Morocco

b. Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakech, Morocco

c. Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany

d. Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany

Correspondence e-mail: bolte@chemie.uni-frankfurt.de

© Ouahrouch et al. 2015

DOI: 10.1107/S2056989015003370

Published online: 28 February 2015

Abstract

In the title compound, C₂₀H₂₄N₂O₄, both peptide bonds adopt a trans configuration with respect to the —N—H and —C=O groups. The dihedral angle between the aromatic rings is 53.58 (4)°. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. The crystal packing is characterized by zigzag chains of N—H⋯O hydrogen-bonded molecules running along the b-axis direction.

Related literature  

For the synthesis of the title compound, see: Xingwen et al. (2007 ▶); Chandrika et al. (2008 ▶). Compounds with quinazoline scaffolds are of biological importance due to their pharmacological activities such as antimicrobial (Jantova et al., 2004 ▶; Shi et al., 2013 ▶), antitumorigenic (Kubo et al., 2005 ▶), antifungal (Dandia et al., 2005 ▶), antihyperglycemic (Ram et al., 2003 ▶), anti-inflammatory (Gineinah et al., 2002 ▶; Baba et al., 1996 ▶), antitumor (Forsch et al., 2002 ▶) and protein kinase inhibitor (Levitzky, 2003 ▶).

Experimental  

Crystal data  

C₂₀H₂₄N₂O₄

M r = 356.41

Monoclinic,

a = 8.4901 (4) Å

b = 14.2281 (7) Å

c = 15.3864 (7) Å

β = 98.659 (4)°

V = 1837.46 (15) Å³

Z = 4

Mo Kα radiation

μ = 0.09 mm⁻¹

T = 173 K

0.36 × 0.35 × 0.32 mm

Data collection  

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.874, T max = 0.892

56243 measured reflections

5148 independent reflections

4676 reflections with I > 2σ(I)

R int = 0.065

Refinement  

R[F ² > 2σ(F ²)] = 0.041

wR(F ²) = 0.110

S = 1.08

5148 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å⁻³

Δρmin = −0.18 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

See full table Table 1. Hydrogen-bond geometry (, )

Supplementary Material

Open In Web Browser

Footnotes

Supporting information for this paper is available from the IUCr electronic archives (Reference: LH5750).

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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References

Baba, A., Kawamura, N., Makino, H., Ohta, Y., Taketomi, S. & Sohda, T. J. (1996). Med. Chem. 39, 5176–5182.

Chandrika, P. M., Yakaiah, T., Raghu Ram Rao, A., Narsaiah, B., Chakra Reddy, N., Sridhar, V. & Venkateshwara Rao, J. (2008). Eur. J. Med. Chem. 43, 846–852.

Dandia, A., Singh, R. & Sarawgi, P. (2005). J. Fluorine Chem. 126, 307–312.

Forsch, R. A., Wright, J. E. & Rosowsky, A. (2002). Bioorg. Med. Chem. 10, 2067–2076.

Gineinah, M. M., El-Sherbeny, M. A., Nasr, M. N. & Maarou, A. R. (2002). Arch. Pharm. Pharm. Med. Chem. 11, 556–562.

Jantova, S., Stankovsky, S. & Spirkova, K. (2004). Biol. Bratislava, 59, 741–752.

Kubo, K., Shimizu, T., Ohyama, S. I., Murooka, H., Iwai, A., Nakamura, K., Hasegawa, K., Kobayashi, Y., Takahashi, N., Takahashi, K., Kato, S., Izawa, T. & Isoe, T. (2005). J. Med. Chem. 48, 1359–1366.

Levitzky, A. (2003). Acc. Chem. Res. 36, 462–469.

Ram, V. J., Farhanullah Tripathi, B. K. & Srivastava, A. K. (2003). Bioorg. Med. Chem. 11, 2439–2444.

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Shi, L. P., Jiang, K. M., Jiang, J. J., Jin, Y., Tao, Y. H., Li, K., Wang, X. H. & Lin, J. (2013). Bioorg. Med. Chem. Lett. 23, 5958–5960.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Xingwen, G., Xuejian, C., Kai, Y., Baoan, S., Lili, G. & Zhuo, C. (2007). Molecules, 12, 2621–2642.

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Table 1. Hydrogen-bond geometry (, )

DHA | DH | HA | D A | DHA
N1H1O2 | 0.886(16) | 1.914(15) | 2.6434(11) | 138.6(14)
N2H2O1i | 0.848(15) | 2.132(15) | 2.9338(12) | 157.6(13)

Symmetry code: (i) .

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