(Z)-3-(2-Amino­anilino)-1-phenyl­but-2-en-1-one

Subramani Karthikeyan; Thothadri Srinivasan; Elumalai Sundaravadivel; Muthusamy Kandaswamy; Devadasan Velmurugan

doi:10.1107/S160053681301060X

. 2013 Apr 24;69(Pt 5):o780. doi: 10.1107/S160053681301060X

(Z)-3-(2-Aminoanilino)-1-phenylbut-2-en-1-one

Subramani Karthikeyan ^a, Thothadri Srinivasan ^a, Elumalai Sundaravadivel ^b, Muthusamy Kandaswamy ^b, Devadasan Velmurugan ^a,^*

PMCID: PMC3648304 PMID: 23723924

Abstract

In the title compound, C₁₆H₁₆N₂O, the phenyl and 2-aminophenyl rings are almost perpendicular to one another, with a dihedral angle of 82.77 (8)°. There is an intramolecular N—H⋯O hydrogen bond in the molecule. In the crystal, molecules are linked via N—H⋯O hydrogen bonds forming chains along [001]. There are also C—H⋯π interactions present, linking the chains to form a three-dimensional structure.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Lin et al. (2002 ▶). For a related chalcone structure, see: Ranjith et al. (2010 ▶). graphic file with name e-69-0o780-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O
M _r = 252.31
Monoclinic,
a = 15.489 (5) Å
b = 16.422 (5) Å
c = 11.684 (5) Å
β = 110.646 (5)°
V = 2781.1 (17) Å³
Z = 8
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 = 0.977, T _max = 0.985
18172 measured reflections
4023 independent reflections
2805 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.152
S = 1.01
4023 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 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

Click here for additional data file.^{(23.8KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301060X/su2583sup1.cif

e-69-0o780-sup1.cif^{(23.8KB, cif)}

Click here for additional data file.^{(193.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301060X/su2583Isup2.hkl

e-69-0o780-Isup2.hkl^{(193.3KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681301060X/su2583Isup3.cml

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

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

Cg1 is the centroid of ring C1–C6.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.95	2.6311 (19)	135
N1—H1A⋯O1ⁱ	0.86	2.28	3.001 (2)	142
N1—H1B⋯O1ⁱⁱ	0.86	2.18	3.034 (2)	174
C14—H14⋯Cg1ⁱⁱⁱ	0.93	2.96	3.773 (3)	147

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

Acknowledgments

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

supplementary crystallographic information

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 anti-tuberculosis agents (Lin et al., 2002). Against this background and in order to obtain detailed information on molecular conformations in the solid state of such compounds, an X-ray study of the title compound was carried out.

In the title compound, Fig. 1, the phenyl ring (C1-C6) makes a dihedral angle of 82.77 (8)° with the 2-aminophenyl ring (C11-C16), which shows that they are almost orthogonal to each other. The amine attached with phenyl ring (C11-C16) deviates by 0.0827 (14) Å. There is an intramolecular N-H···O hydrogen bond in the molecule (Table 1 and Fig. 1)

In the crystal, molecules are linked via N–H···O hydrogen bonds forming chains along the c axis direction. There are also C-H···π interactions present linking the chains to form a three-dimensional structure (see Table 1 and Fig. 2).

Experimental

To a solution of 1-benzoylacetone (2 g, 12.3 mmol) in chloroform (25 ml), 1,2-diaminobenzene (1.33 g, 12.3 mmol) in chloroform (25 ml) was added with stirring. The yellow coloured solid product was collected by filtration and washed with water to remove unreacted 1,2-diaminobenzene. The microcrystalline compound was recrystallized from hot chloroform giving yellow crystals of the title compound, suitable for X-ray diffraction analysis, on slow evaporation of the solvent [Yield: 51%; M.p. 382 K].