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

T S Arul Jeevan; K S Nagaraja

doi:10.1107/S1600536808043183

. 2008 Dec 24;65(Pt 1):o206. doi: 10.1107/S1600536808043183

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

T S Arul Jeevan ^a,^*, K S Nagaraja ^a

PMCID: PMC2968111 PMID: 21581660

Abstract

The title compound, C₁₃H₁₇NO₂, has an intramolecular N—H⋯O hydrogen bond, forming a planar six-membered ring with a mean deviation of 0.015 (5) Å from the plane. This plane makes a dihedral angle of 7.19 (8)° with the adjacent phenyl ring. Through an intermolecular O—H⋯O hydrogen bond, the molecules with their 2₁ screw and b-translation equivalents form a helical chain running parallel to the b axis.

Related literature

For general background, see: Morozova et al. (2007 ▶). For a related structure, see: Shi (2005 ▶).

Experimental

Crystal data

C₁₃H₁₇NO₂
M _r = 219.28
Orthorhombic,
a = 5.9131 (3) Å
b = 8.0101 (4) Å
c = 24.9626 (13) Å
V = 1182.34 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.944, T _max = 0.984
11541 measured reflections
1236 independent reflections
1168 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.079
S = 1.05
1236 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.09 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043183/is2371sup1.cif

e-65-0o206-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043183/is2371Isup2.hkl

e-65-0o206-Isup2.hkl^{(59.8KB, 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
O2—H2A⋯O1ⁱ	0.82	1.99	2.805 (2)	176
N1—H1N⋯O1	0.85 (2)	1.94 (2)	2.642 (2)	139.1 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors express their thanks to the Sophisticated Analytical Instruments Facility, Indian Institute of Technology Madras, Chennai, for the collection of X-ray diffraction data. The authors are also grateful to the Department of Science and Technology (DST), India, for financial support (SR/S3/ME/03/2005-SERC) to carry out this work.

supplementary crystallographic information

Comment

The Schiff base 1-phenyl-3-[(3-hydroxypropyl)amino]-1-butanone could be a good chelating ligand and may find use in the field of coordination chemistry of transition metal complexes. The compound could act as a bidentate ligand through the N and O atoms. The replacement of oxygen by nitrogen in the ligand can increase the covalency of the complexes (Morozova et al., 2007).

Figure 1 gives ORTEP representation of the molecule with atoms represented as 50% anisotropic ellipsoids. Figure 2 gives packing of the molecules showing hydrogen bonded interactions. The molecules and their 2₁ screw translation equivalents are bound through O2—H2A···O1 hydrogen bonds (Table 1). These H-bonded pairs are further linked with their b-translation equivalents to form an one-dimensional hydrogen bonded network parallel to b axis. There is an intramolecular N1—H1···O1 hydrogen bond between the imino hydrogen and the keto oxygen (Table 1). The packing is further stabilized through van der Waals interactions. The crystal is found to cleave easily through the (001) plane. The closely related compound, C₁₂H₁₅O₂N, (3-[(2-hydroxyethyl)amino]-1-phenylbut-2-en-1-one) crystallizes in monoclinic system with centrosymmetric space group P2₁/n, forming hydrogen bonded dimers in the structure (Shi, 2005), while the title compound crystallizes in polar space group P2₁2₁2₁ and with extended hydrogen bonding in the structure.

Experimental

The title Schiff base ligand was synthesized by the condensation of 3-amino-1-propanol and benzoylacetone. To 0.1 molar solution of 3-amino-1-propanol (dissolved in 5 ml of ethanol) was slowly added to a 0.1 molar solution (in ethanol) of benzoylacetone. The reaction mixture was refluxed for 30 min. The solution was cooled overnight and the precipitate was washed with ethanol. The compound was crystallized in ethanol by slow evaporation (m.p. = 394 K). Anal. Calc. for C₁₃H₁₈O₂N: (Found %): C 70.88 (69.96), H 8.24 (8.13), N 6.35 (6.26). IR (KBr, cm^-1): 3170 = v(O—H); 3340, v(N—H); 1596, v[(C—N)—C=C)]; 1265, v(C—O). ¹H NMR (400 MHz, CDCl₃) δ values at 1.8, 2.0, 3.4, 3.6, 5.7 and 7.4 p.p.m. for CH₃, CH₂, NH—CH₂, CH₂—OH, H—C=C and aromatic protons respectively. ¹³C NMR (400 MHz, CDCl₃) δ values at 14.83, 32.53, 40.06, 92.46, 128, 140.39 and 187 for CH₃, CH₂,-HN—CH₂, –CH₂OH, Aromatic, C—CH=C– and C=O carbon respectively. Mass Spectra: M+, m/z = 220.29, (I = 19%); M [L-(O—CH₂—CH₂—CH₂—N)]+, 148.10, (22); M [(C₆H₅-C=O)]+, 104.52, (100); M [(O—CH₂—CH₂—CH₂—N)]+, 74.63, (65).