(E)-3,3,6,6-Tetra­methyl-9-(2-nitro­styr­yl)-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

Jae Kyun Lee; Sun-Joon Min; Yong Seo Cho; Ki Soo Lee; Joo Hwan Cha

doi:10.1107/S1600536812023495

. 2012 May 31;68(Pt 6):o1947. doi: 10.1107/S1600536812023495

(E)-3,3,6,6-Tetramethyl-9-(2-nitrostyryl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Jae Kyun Lee ^a, Sun-Joon Min ^a, Yong Seo Cho ^a, Ki Soo Lee ^b, Joo Hwan Cha ^b,^*

PMCID: PMC3379499 PMID: 22719697

Abstract

In the title compound, C₂₅H₂₇NO₅, each of the cyclohexenone rings adopts a half-chair 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. In the crystal, weak C—H⋯O hydrogen bonds link molecules into chains parallel to the c axis.

Related literature

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

Experimental

Crystal data

C₂₅H₂₇NO₅
M _r = 421.49
Monoclinic,
a = 33.312 (3) Å
b = 9.4144 (6) Å
c = 14.4581 (10) Å
β = 102.3931 (19)°
V = 4428.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.753, T _max = 0.974
20666 measured reflections
5066 independent reflections
3965 reflections with F ² > 2.0σ(F ²)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.153
S = 1.05
5066 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 in 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) global, I. DOI: 10.1107/S1600536812023495/ff2067sup1.cif

e-68-o1947-sup1.cif^{(45.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023495/ff2067Isup2.hkl

e-68-o1947-Isup2.hkl^{(248.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023495/ff2067Isup3.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
C17—H17⋯O5ⁱ	0.93	2.49	3.420 (3)	176

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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

Comment

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

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Cha et al., 2012). All two cyclohexenone rings in (I) display half-chair conformation, whereas the pyran ring adopts a boat conformation.

In the crystal, weak intermolecular C17—H17···O5 hydrogen bonds into chains parallel to the c axis.

Experimental

To solution of (E)-2.2-(3-(2-Nitrophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxy-5,5-δimethylcyclohex-2-enone) (1.25 mmol) in methanol (12.5 ml) was added catalytic amount of sulfuric acid under nitrogen atmosphere. After stirring for 3 h, 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 residue solid was purified by recrystallization from a mixture of ethanol and methylene chloride (1:1) to afford colorless block type crystals suitable for X-ray analysis.