2,2′-Bis(9-hydr­oxy-9-fluoren­yl)biphen­yl–ethyl acetate (1/1)

Lidiya Izotova; Jamshid Ashurov; Bakhtiyar Ibragimov; Edwin Weber

doi:10.1107/S1600536808023271

. 2008 Jul 31;64(Pt 8):o1627. doi: 10.1107/S1600536808023271

2,2′-Bis(9-hydroxy-9-fluorenyl)biphenyl–ethyl acetate (1/1)

Lidiya Izotova ^a,^*, Jamshid Ashurov ^a, Bakhtiyar Ibragimov ^a, Edwin Weber ^b

PMCID: PMC2962236 PMID: 21203317

Abstract

In the title host–guest compound, C₃₈H₂₆O₂·C₄H₈O₂, the ethyl acetate molecule (guest), which adopts a fully extended conformation, and the biphenyl derivative (host) are connected via O—H⋯O hydrogen bonds [H⋯O = 1.90 (3) Å] into discrete assemblies. The hydrocarbon skeleton of the host molecule deviates only slightly from C₂ symmetry. The OH groups of the host are involved in intramolecular O—H⋯O hydrogen bonding [H⋯O = 1.83 (3) Å].

Related literature

For related literature, see: Barbour et al. (1993 ▶); Ibragimov et al. (2001 ▶); Sardone (1996 ▶); Sumarna et al. (2003 ▶); Weber et al. (1993 ▶).

Experimental

Crystal data

C₃₈H₂₆O₂·C₄H₈O₂
M _r = 602.69
Monoclinic,
a = 11.645 (2) Å
b = 16.364 (3) Å
c = 17.471 (3) Å
β = 97.72 (3)°
V = 3299.1 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.4 × 0.2 × 0.2 mm

Data collection

Stoe STADI4 diffractometer
Absorption correction: none
5807 measured reflections
5650 independent reflections
3654 reflections with I > 2σ(I)
3 standard reflections every 100 reflections intensity decay: 2.6%

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.141
S = 1.20
5650 reflections
424 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023271/gk2155sup1.cif

e-64-o1627-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023271/gk2155Isup2.hkl

e-64-o1627-Isup2.hkl^{(276.6KB, 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
O2—H1⋯O3ⁱ	0.88 (4)	1.90 (4)	2.779 (3)	173 (4)
O1—H2⋯O2	0.93 (4)	1.84 (4)	2.739 (3)	161 (3)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Crystalline inclusion compounds (clathrates, host–guest complexes) are of increasing importance in supramolecular chemistry because of their significant potential in addressing a variety of fundamental and practical issues. 2,2'-Bis(9-hydroxy-9-fluorenyl)biphenyl (I) is a host compound with good clathrate-forming ability and the crystal structures of its inclusion compounds with acetonitrile, cyclohexanone, n-propylamine (Barbour et al., 1993), acetone (three solvates) (Sardone, 1996; Ibragimov et al., 2001) and chloroform (two solvates) (Sumarna et al., 2003) were reported. Here, we report the crystal structure of a host–guest complex of (I) with ethyl acetate which resembles closely that of (I) with acetone (1/1) (Sardone, 1996). The molecule of (I) has three conformational degrees of freedom (rotation around the central aryl–aryl single bond and rotations around the aryl–fluorenyl bonds), however it exhibits considerable conformational rigidity due to the stabilizing effect of the intramolecular O—H···O hydrogen bond between the hydroxyl groups (Fig. 1, Table 1). The crystal packing is mainly stabilized by van der Waals forces (Fig.2).

Experimental

2,2'-Bis(9-hydroxy-9-fluorenyl)biphenyl was synthesized according to the procedure described by Weber et al., (1993). The stable in the air crystals were grown by slow evaporation from ethyl acetate solution.