(Z)-3-[(2-Amino­benz­yl)amino]-1-phenyl­but-2-en-1-one

Vedavalli Sairaj; Thothadri Srinivasan; Muthusamy Kandaswamy; Devadasan Velmurugan

doi:10.1107/S1600536814012070

. 2014 Jun 4;70(Pt 7):o742. doi: 10.1107/S1600536814012070

(Z)-3-[(2-Aminobenzyl)amino]-1-phenylbut-2-en-1-one

Vedavalli Sairaj ^a, Thothadri Srinivasan ^b, Muthusamy Kandaswamy ^a, Devadasan Velmurugan ^b,^*

PMCID: PMC4120556 PMID: 25161539

Abstract

In the title compound, C₁₇H₁₈N₂O, the aromatic rings are almost normal to one another, making a dihedral angle of 89.00 (8)°. There is an intramolecular N—H⋯O hydrogen bond in the molecule enclosing an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains along [010].

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Lin et al. (2002 ▶). For a related structure, see: Ranjith et al. (2010 ▶). graphic file with name e-70-0o742-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₈N₂O
M _r = 266.33
Monoclinic,
a = 11.3197 (4) Å
b = 9.8341 (3) Å
c = 13.4207 (4) Å
β = 106.387 (2)°
V = 1433.29 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.698, T _max = 0.746
14860 measured reflections
3921 independent reflections
2528 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.156
S = 1.03
3921 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012070/su2735sup1.cif

e-70-0o742-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012070/su2735Isup2.hkl

e-70-0o742-Isup2.hkl^{(188.3KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814012070/su2735Isup3.cml

CCDC reference: 1005094

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.99	2.6619 (17)	134
N1—H1A⋯O1ⁱ	0.86	2.27	3.0009 (19)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for data collection. TS also thanks the DST for an Inspire Fellowship. The UGC (SAP–CAS) is acknowleged for departmental facilities.

supplementary crystallographic information

S1. Comment

Chalcones are a major class of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff and have recently been the subject of great interest for their interesting pharmacological activities (Di Carlo et al., 1999). Chalcones and flavonoids have been reported to be active anti-tuberculosis agents (Lin et al.,2002). Against this background and in order to obtain detailed information on molecular conformation in the solid state, an X-ray study of the title compound was carried out.

In the title compound, Fig. 1, the aminobenzyl ring (C1-C6) and the phenyl ring (C12-C17) are normal to one another with a dihedral angle of 89.00 (8)°. The amine N atom, N1, attached to phenyl ring (C1-C6), deviates by only -0.0020 (16) Å from the ring plane. There is an intramolecular N-H···O hydrogen bonds enclosing an S(6) ring motif.

In the crystal, molecules are linked by N–H···O hydrogen bonds forming chains along the b axis direction (Table 1 and Fig. 2).

S2. Experimental

To a warm ethanolic solution (25 ml) of 2-aminobenzylamine (0.25 g, 0.2 mmol), an ethanolic solution of benzylacetone (0.3 g, 0.2 mmol) was added dropwise and the resulting solution was refluxed for 3 h. The solution was then filtered hot and allowed to stand at room temperature. After slow evaporation of the solvent at 298 K, block-like colourless crystals of the title compound were obtained. They were filtered off, washed with cold methanol and dried [Yield 0.45 g, 83%].