3-[(1-Hy­droxy-1-phenyl­propan-2-yl)amino]-5,5-dimethyl­cyclo­hex-2-enone

Mostafa M Ghorab; Mansour S Al-Said; Saleh I Alqasoumi; Tze Shyang Chia; Hoong-Kun Fun

doi:10.1107/S160053681201570X

. 2012 Apr 18;68(Pt 5):o1436–o1437. doi: 10.1107/S160053681201570X

3-[(1-Hydroxy-1-phenylpropan-2-yl)amino]-5,5-dimethylcyclohex-2-enone

Mostafa M Ghorab ^a, Mansour S Al-Said ^a, Saleh I Alqasoumi ^b, Tze Shyang Chia ^c, Hoong-Kun Fun ^c,^*,^‡

PMCID: PMC3344556 PMID: 22590318

Abstract

The asymmetric unit of the title compound, C₁₇H₂₃NO₂, consists of two crystallographically independent molecules (A and B). The cyclohexene rings in both molecules adopt an envelope conformation. In the crystal, independent molecules, A and B, are each linked by intermolecular bifurcated (N,O)—H⋯O hydrogen bonds, generating R ₂ ¹(7) ring motifs and forming infinite chains along the b axis.

Related literature

For cyclohex-2-enone derivatives and their biological activity, see: Ghorab et al. (2009 ▶, 2010 ▶); Ghorab, Al-Said & El-Hossary (2011 ▶); Aghil et al. (1992 ▶); Li & Strobel (2001 ▶). For the biological activity of phenylpropan-2-ylamino, see: Zhang et al. (2011 ▶). For the synthesis of biologically active heterocyclic compounds, see: Ghorab et al. (2012 ▶); Ghorab, Ragab et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₂₃NO₂
M _r = 273.36
Monoclinic,
a = 10.4357 (6) Å
b = 12.4953 (8) Å
c = 12.8706 (5) Å
β = 107.019 (3)°
V = 1604.79 (15) Å³
Z = 4
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 296 K
0.80 × 0.59 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.654, T _max = 0.983
8364 measured reflections
3114 independent reflections
2426 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.150
S = 1.08
3114 reflections
379 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201570X/is5115sup1.cif

e-68-o1436-sup1.cif^{(38.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201570X/is5115Isup2.hkl

e-68-o1436-Isup2.hkl^{(152.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201570X/is5115Isup3.cml

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
N1B—H1NB⋯O1Bⁱ	0.82 (6)	2.12 (6)	2.874 (4)	155 (5)
O2B—H1OB⋯O1Bⁱ	0.96 (7)	1.75 (7)	2.701 (4)	170 (6)
N1A—H1NA⋯O1Aⁱⁱ	0.85 (6)	2.04 (6)	2.853 (4)	160 (5)
O2A—H1OA⋯O1Aⁱⁱ	0.91 (7)	1.88 (7)	2.724 (4)	155 (6)

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

Acknowledgments

MMG, MSAS and SIA are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University, Riyadh, Saudia Arabia. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of research fellowship.

supplementary crystallographic information

Comment

From literature survey it was found that cyclohex-2-enone derivatives are useful in the synthesis of heterocyclic compounds, especially quinoline derivatives (Ghorab et al., 2009, 2010; Ghorab, Al-Said & El-Hossary, 2011). Cyclohex-2-enone derivatives also exhibit a wide range of biological activities such as anticancer (Aghil et al., 1992) and antimicrobial (Li & Strobel, 2001) activities. On the other hand, compounds having the phenylpropan-2-ylamino moiety are also known to possess a wide range of biological and pharmacological activities, especially anticancer activity (Zhang et al., 2011). In the light of these facts and as a continuation of our efforts towards synthesizing biologically active heterocyclic compounds (Ghorab, Ragab et al., 2011; Ghorab et al., 2012), we prepared a novel cyclohex-2-enone carrying a biologically active phenylpropan-2-ylamino moiety to evaluate its anticancer activity.

The asymmetric unit of the title compound consists of two crystallographically independent molecules (A and B) as shown in Fig. 1. In both molecules, the cyclohexene rings adopt an envelope conformation with puckering parameters (Cremer & Pople, 1975), Q = 0.436 (5) Å, θ = 128.6 (7)° and φ = 45.0 (8)° in molecule A [Q = 0.448 (4) Å, θ = 124.1 (5)° and φ = 54.4 (6)° in molecule B]. The distance of atom C5 from the mean plane of C1–C4/C6 is 0.5989 (68) Å in molecule A, whereas in molecule B, the corresponding distance is 0.6264 (51) Å. In molecule A, the mean plane of O1/C1–C4/C6 [maximum deviation = 0.0704 (30) Å at atom C6] forms dihedral angle of 61.13 (18)° with the terminal C9–C14 benzene ring, whereas in molecule B, the corresponding maximum deviation and dihedral angle are 0.0261 (27) Å at atom C1 and 56.20 (16)°, respectively.

In the crystal (Fig. 2), molecules are linked by intermolecular bifurcated N1A—H1NA···O1A, N1B—H1NB···O1B, O2A—H1OA···O1A and O2B—H1OB···O1B hydrogen bonds (Table 1), generating R₂¹(7) ring motifs (Bernstein et al., 1995) and forming infinite chains along the b axis.

Experimental

A mixture of 5,5-dimethylcyclohexane-1,3-dione (1.4 g, 0.01 mole) and 2-amino-1-phenylpropan-1-ol (1.51 g, 0.01 mole) in dry dimethylformamide (10 ml) containing triethylamine (3 drops) as catalyst was refluxed for 8 h. The obtained solid was recrystallized from ethanol to give the title compound. Single crystals which are suitable for an X-ray structural analysis were obtained by slow evaporation from ethanol at room temperature.