Ethyl N-(2-benzoyl-3-oxo-3-phenyl­propano­yl)carbamate

Mehmet Akkurt; Ahmet Oral Sarıoğlu; Mehmet Sönmez; Muhammad Nawaz Tahir

doi:10.1107/S1600536813000445

. 2013 Jan 12;69(Pt 2):o220. doi: 10.1107/S1600536813000445

Ethyl N-(2-benzoyl-3-oxo-3-phenylpropanoyl)carbamate

Mehmet Akkurt ^a,^*, Ahmet Oral Sarıoğlu ^b, Mehmet Sönmez ^b, Muhammad Nawaz Tahir ^c,^*

PMCID: PMC3569755 PMID: 23424501

Abstract

In the title compound, C₁₉H₁₇NO₅, the dihedral angle between the phenyl groups is 79.55 (15)°. The terminal ethoxy group is disordered over two orientations in a 0.873 (6):0.127 (6) ratio. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into [001] chains which incorporate R ₁ ²(6) loops. A very weak C—H⋯π contact also occurs.

Related literature

For background to the carboxamide [–C(O)NH–] group, see: Sönmez (2001 ▶). For further synthetic details, see: Fabian et al. (1992 ▶).

Experimental

Crystal data

C₁₉H₁₇NO₅
M _r = 339.34
Monoclinic,
a = 33.088 (8) Å
b = 12.732 (3) Å
c = 8.7110 (18) Å
β = 97.896 (9)°
V = 3635.0 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.35 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.981, T _max = 0.986
14531 measured reflections
3579 independent reflections
1910 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.132
S = 1.01
3579 reflections
234 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

Click here for additional data file.^{(27.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000445/hb7023sup1.cif

e-69-0o220-sup1.cif^{(27.7KB, cif)}

Click here for additional data file.^{(172KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000445/hb7023Isup2.hkl

e-69-0o220-Isup2.hkl^{(172KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000445/hb7023Isup3.cml

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

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

Cg2 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.37	3.025 (2)	133
N1—H1⋯O4ⁱ	0.86	2.08	2.842 (2)	147
C8—H8⋯O3ⁱ	0.98	2.38	3.263 (3)	150
C19B—H19F⋯Cg2ⁱⁱ	0.96	2.96	3.786 (5)	145

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The carboxamide [–C(O)NH–] group, which seems to be everywhere throughout nature in the primary structure of proteins, is an important ligand construction unit for coordination chemists (Sönmez, 2001). The high stability of the amide linkage toward hydrolysis is of crucial importance to biological systems, since it allows the construction of peptides from relatively simple amino acid precursors.

In the title compound (I), (Fig. 1), the C1–C6 and C10–C15 phenyl rings make a dihedral angle of 79.55 (15)° with each other. The C7–C8–C16–O3, C8–C16–N1–C17, O3–C16–N1–C17, C16–N1–C17–O4 and C16–N1–C17–O5 torsion angles are -23.0 (3), -176.6 (2), 3.9 (4), 2.6 (4) and -177.2 (2)°, respectively.

In the crystal structure, N—H···O and C—H···O hydrogen bonds (Table 1, Fig. 2) connect the neighbouring molecules, into chains running along the c axis, forming the R²₁(6) motifs (Fig. 2). Furthermore, C—H···π interactions between the H19F hydrogen atom of the methyl group and the C10–C15 phenyl ring (with centroid Cg2) is also observed (Table 1).

Experimental

Dibenzoylaceticacid-N-carboxyethylamide was prepared from reaction of 4-benzoyl-5-phenyl-2,3-furandione and ethyl urethane as the method reported earlier (Fabian et al., 1992). These compounds were refluxed in benzene for 5 h. The solvent was evaporated under reduced pressure to give an oily residue which was treated with ether and finally crystallized from absolute ethanol as colourless needles. Analysis calculated for (C₁₉H₁₇NO₅): C 67.25, H 5.01, N 4.14. Found: C 67.22, H 5.06, N 4.30.