7-Bromo-4-(7-bromo-3,3-dimethyl-1-oxo-2,3,4,9-tetra­hydro-1H-xanthen-9-yl)-3,3-dimethyl-2,3-dihydroxanthen-1(4H)-one ethanol solvate

Chaomei Lian; Pingping Lu; Yulin Zhu

doi:10.1107/S1600536809035922

. 2009 Sep 12;65(Pt 10):o2448. doi: 10.1107/S1600536809035922

7-Bromo-4-(7-bromo-3,3-dimethyl-1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-3,3-dimethyl-2,3-dihydroxanthen-1(4H)-one ethanol solvate

Chaomei Lian ^a, Pingping Lu ^a, Yulin Zhu ^a,^*

PMCID: PMC2970291 PMID: 21577903

Abstract

The title compound, C₃₀H₂₆Br₂O₄·C₂H₅OH, was synthesized from the reaction between 5-bromosalicybenzaldehyde and 5,5-dimethyl-1,3-cyclohexanedione. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds and C—H⋯O interactions.

Related literature

For the properties and applications of xanthenes, see: Gusak et al. (2000 ▶); Sato et al. (2008 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C₃₀H₂₆Br₂O₄·C₂H₆O
M _r = 656.40
Orthorhombic,
a = 15.016 (2) Å
b = 10.2459 (14) Å
c = 18.740 (3) Å
V = 2883.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 298 K
0.26 × 0.18 × 0.12 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.546, T _max = 0.710
14442 measured reflections
5155 independent reflections
3685 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.078
S = 1.01
5155 reflections
357 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ▶), 2379 Friedel pairs
Flack parameter: 0.020 (8)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035922/jh2097sup1.cif

e-65-o2448-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035922/jh2097Isup2.hkl

e-65-o2448-Isup2.hkl^{(252.5KB, 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
C14—H14B⋯O3	0.96	2.40	3.280 (6)	152
O5—H5⋯O1ⁱ	0.82	2.13	2.908 (7)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank South China Normal University for financial support (grant Nos. SCNU033038 and SCNU524002).

supplementary crystallographic information

Comment

Organic molecules containing xanthene are of biological importance and useful in drug discovery. They are also very efficient laser dyes and outstanding photophysical properties. (Gusak et al., 2000; Sato et al., 2008; Wang et al., 2005). As one part of our on going studies on the synthesis of xanthene-containing heterocyclic compounds, the title compound was isolated unexpectedly.

The reaction between 5-bromosalicybenzaldehyde and 5,5-dimethyl-1,3-cyclohexanedione proceeded to give the title compound in excellent yield in the presence of palladium(II) chloride as catalyst in acetonitrile under reflux (Figure 1). The structure of the title compound is illustrated in Figure 2. There are no unusual bond lengths and angles in the compound. The phenyl rings show no interactions in the crystal. The compound contains two similar linked rings: a pyranoid ring connected two six-membered rings, the structure about two big rings connected each other via C3—C23 bond. The two big rings are approximately planar (Figure 3). In addition, the molecule is connected with the ethanol molecule by O(5)—H(5)···O(1) and interior C(14)—H(14)···O(3), which is less than the sum of their van der Waals.

Experimental

A mixture of 5-bromosalicybenzaldehyde (1.00g, 5mmol), 5,5-dimethyl-1,3-cyclohexanedione (1.12 g, 10 mmol), thiourea (0.76 g, 10 mmol), and palladium(II) chloride was refluxed in acetonitrile (12 ml) at 298 K for 12 h. After being cooled to room temperature, The red precipitation was filtered through a silica pad, and then washed twice with water, dried under vacuum to yield the product. Single crystal of the title compound was obtained by slow evaporation from ethanol at room temperature. The compound is isolated as red, block-shaped crystal from ethanol at room temperature.