9-[(E)-2-(4-Chloro­phen­yl)ethen­yl]-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

Byung-Yong Yu; Jae Kyun Lee; Yong Seo Cho; Sun-Joon Min; Jae Chun Woo

doi:10.1107/S1600536813025026

. 2013 Sep 18;69(Pt 10):o1542. doi: 10.1107/S1600536813025026

9-[(E)-2-(4-Chlorophenyl)ethenyl]-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

Byung-Yong Yu ^a, Jae Kyun Lee ^b,^*, Yong Seo Cho ^b, Sun-Joon Min ^b, Jae Chun Woo ^c

PMCID: PMC3790409 PMID: 24098228

Abstract

In the title compound, C₂₅H₂₇ClO₃, each of the cyclohexenone rings adopts an envelope conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. The C=C double bond is in the trans conformation. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains running parallel to the b axis.

Related literature

For the synthesis and the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2013 ▶); Lee et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C₂₅H₂₇ClO₃
M _r = 410.94
Monoclinic,
a = 5.9686 (4) Å
b = 18.7567 (13) Å
c = 20.1089 (13) Å
β = 100.9322 (18)°
V = 2210.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.40 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR, Rigaku, 1995 ▶) T _min = 0.629, T _max = 0.981
21185 measured reflections
5042 independent reflections
2842 reflections with F ² > 2.0σ(F ²)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.194
S = 1.11
5042 reflections
274 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813025026/ff2119sup1.cif

e-69-o1542-sup1.cif^{(44KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025026/ff2119Isup2.hkl

e-69-o1542-Isup2.hkl^{(246.9KB, hkl)}

Click here for additional data file.^{(8.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813025026/ff2119Isup3.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
C23—H23B⋯O2ⁱ	0.96	2.53	3.461 (4)	163

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Symmetry code: (i) Inline graphic .

Acknowledgments

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

supplementary crystallographic information

1. Comment

As part of our ongoing study of the substituent effect on the solid state structures of xanthene derivatives (Cha et al., 2013; Lee et al., 2012, 2013). We present here the crystal structure of the title compound (I) (Fig. 1).

The starting material, (E)-2.2-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl) bis(3-hydroxy-5,5-δimethylcyclohex-2-enone) was prepared according to the reported method (Cha et al., 2013). In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Lee et al., 2013).

The torsion angle C2—C1—C14—C15 between the benzene ring (C16 - C21) system and the pyran ring (C1—C2—C7—O3—C8—C13) is 41.74 (2)°. The double bond [C14=C15] is in the trans conformation. All two cyclohexenone rings in (Fig.1) display envelope conformation, whereas the pyran ring adopts a boat conformation.

In the crystal, weak intermolecular C—H···O hydrogen bonds link molecules into chains running parallel to the b-axis.

2. Experimental

To solution of (E)-2.2-(3-(4-Chlorophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxy-5,5-dimethylcyclohex-2-enone) (1.25 mmol) was added methanol and catalytic amounts of sulfuric acid in under nitrogen atmosphere. After stirring for 4 h, the progress of reaction was monitored by TLC. The solvent was evaporated and the remaining residue dissolved in ethyl acetate. The mixture was neutralized with saturated sodium bicarbonate and the solution was extracted with ethyl acetate. The resulting solid residue was purified by recrystallization from ethanol and methylene chloride (1:7 v/v) to afford (yield 95%) colorless block type crystals suitable for X-ray analysis.