9-(2-Hy­droxy-6-oxocyclo­hex-1-en-1-yl)-2,3,4,9-tetra­hydro-1H-xanthen-1-one

Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Aamer Saeed; Ulrich Flörke

doi:10.1107/S1600536813007952

. 2013 Mar 28;69(Pt 4):o616–o617. doi: 10.1107/S1600536813007952

9-(2-Hydroxy-6-oxocyclohex-1-en-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one

Shaaban K Mohamed ^a,^*, Mehmet Akkurt ^b, Antar A Abdelhamid ^a, Aamer Saeed ^c, Ulrich Flörke ^d

PMCID: PMC3629652 PMID: 23634139

Abstract

In the xanthene ring system in the title compound, C₁₉H₁₈O₄, the 4H-pyran ring has a maximum deviation of 0.110 (2) Å from planarity and the cyclohexene ring exhibits a puckered conformation [puckering parameters Q _T = 0.452 (3) Å, θ = 57.0 (4) and ϕ = 131.7 (4)°]. The cyclohexene ring attached to the xanthene system adopts an envelope conformation, with the middle of the three methylene C atoms as the flap atom. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds form infinite chains of R ₁ ²(6) ring motifs along [100] with the xanthene groups arranged in an alternating zigzag manner.

Related literature

For the bioactivity of xanthene compounds, see: Mohamed et al. (2012a ▶); Mo et al. (2010 ▶) and for their fluorescence properties, see: Menchen et al. (2003 ▶). For similar structures see: Mohamed et al. (2011 ▶, 2012b ▶); Kurbanova et al. (2012 ▶); Abdelhamid et al. (2011 ▶); Reddy et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₉H₁₈O₄
M _r = 310.33
Orthorhombic,
a = 13.4420 (18) Å
b = 8.0015 (10) Å
c = 14.2416 (18) Å
V = 1531.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 130 K
0.37 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.966, T _max = 0.986
13880 measured reflections
1901 independent reflections
1799 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.111
S = 1.06
1901 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: 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/S1600536813007952/nk2202sup1.cif

e-69-0o616-sup1.cif^{(27.7KB, cif)}

Click here for additional data file.^{(93.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007952/nk2202Isup2.hkl

e-69-0o616-Isup2.hkl^{(93.6KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S1600536813007952/nk2202Isup3.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
O2—H2⋯O1ⁱ	0.84	1.76	2.582 (2)	164
C5—H5A⋯O1ⁱ	0.99	2.42	3.034 (3)	119

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Symmetry code: (i) Inline graphic .

Acknowledgments

Manchester Metropolitan University, Universität Paderborn, Erciyes University and Quaid-I-Azam University are gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

Due to the great spectroscopic and biological applications of xanthene molecules, they attracted an excessive interest of researchers in different fields of medicinal and applied chemistry. Such derivatives have exhibited fluorescence properties (Menchen et al., 2003) in addition to their fungicidal, bactericidal and anti-inflammatory possessions (Mohamed et al., 2012a; Mo et al., 2010). As part of our on-going study on synthesis of potential biologically active molecules based xanthene core structure compounds, herein we report the synthesis and structural study of the title compound.

The title compound (I) is shown in Fig. 1. In the xanthene ring system (O3/C7–C19) of (I), the 4H-pyran ring (O3/C7/C8/C13/C14/C19) is nearly planar [maximum deviation = 0.110 (2) Å] and the cyclohexene ring (C14–C19) is puckered with the puckering parameters (Cremer & Pople, 1975) of Q_T = 0.452 (3) Å, θ = 57.0 (4) ° and φ = 131.7 (4) °. The cyclohexene ring (C1–C6) attached to the xanthene system adopts an envelope conformation with the puckering parameters of Q_T = 0.477 (3) Å, θ = 60.5 (2) ° and φ = 178.1 (3) °. The bond lengths and bond angles fall within a normal range and are comparable with those of the similar structures previously reported (Mohamed et al., 2012b; Kurbanova et al., 2012; Abdelhamid et al., 2011; Mohamed et al., 2011; Reddy et al., 2009).

Intermolecular O2—H···O1ⁱ and C5—H5A···O1ⁱ [(i): x - 0.5, -y + 1.5, z; Table 1] hydrogen bonds form infinite chains of R²₁(6)ring motifs (Bernstein et al., 1995; Fig. 2) along the a axis with xanthen groups in alternating zigzag manner.

Experimental

The title compound was obtained as a major product from a three component reaction of 112 mg (1 mmol) cyclohexane-1,3-dione, 112 mg(1 mmol)salicylaldehyde and 137 mg (1 mmol) 1-(3-aminophenyl)ethanol in 50 ml ethanol [the amino alcohol in this reaction has not been reacted instead acted as a Lewis base catalyst]. The reaction mixture was refluxed for 3 h at 350 K, then cooled at room temperature in fume cupboard where the excess solvent was evaporated. The solid that formed was filtered off, washed with cold ethanol and dried under vacuum. On crystallization from ethanol shiny crystals (m.p. 503 K) were collected in an excellent yield (92%). Crystals suitable for X-ray diffraction were grown by slow evaporation method over two days using ethanol solution.