11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.02,7.015,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene

Xia Tian; Jian-Rong Han; Xiao-Li Zhen; Zhen-Chao Li; Shou-Xin Liu

doi:10.1107/S1600536809025070

. 2009 Jul 8;65(Pt 8):o1792. doi: 10.1107/S1600536809025070

11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.0^2,7.0^15,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene

Xia Tian ^a, Jian-Rong Han ^a,^*, Xiao-Li Zhen ^a, Zhen-Chao Li ^a, Shou-Xin Liu ^b,^‡

PMCID: PMC2977147 PMID: 21583498

Abstract

In the title compound, C₂₅H₂₃N₃O₅S, the central 1,3,4-oxadiazole ring makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, with the three benzene rings. In the crystal structure, the packing is stabilized by weak non-classical intermolecular C—H⋯O hydrogen bonds, which link the molecules into an infinite network.

Related literature

For related structures, see: Du, Hua & Jin (2001 ▶). For applications and synthesis of fluorescent sensors, see: Tong et al. (2000 ▶); Silva et al. (2000 ▶); Valeur & Leray (2000 ▶). For reference geometrical data, see: Du, Hua, Wang & Yan (2001 ▶).

Experimental

Crystal data

C₂₅H₂₃N₃O₅S
M _r = 477.52
Monoclinic,
a = 13.0474 (19) Å
b = 9.6809 (14) Å
c = 18.261 (3) Å
β = 97.479 (3)°
V = 2286.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 294 K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.932, T _max = 0.964
12599 measured reflections
4656 independent reflections
2878 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.106
S = 1.01
4656 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 I, global. DOI: 10.1107/S1600536809025070/pv2175sup1.cif

e-65-o1792-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025070/pv2175Isup2.hkl

e-65-o1792-Isup2.hkl^{(228.1KB, 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
C10—H10A⋯O4ⁱ	0.97	2.52	3.424 (3)	154
C20—H20⋯O4ⁱ	0.93	2.39	3.314 (3)	173
C5—H5⋯O4ⁱⁱ	0.93	2.51	3.253 (3)	137

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the NSFC of Hebei Province (No. B2009000670), the Foundation of the Education Department of Hebei Province and the Foundation of Hebei University of Science & Technology (No. XL200746), which are gratefully acknowledged.

supplementary crystallographic information

Comment

The development of fluorescent sensors for organic molecules is of great practical importance in chemical, biological, and pharmaceutical sciences (Silva et al., 2000; Valeur et al., 2000). Therefore, the design and synthesis of new functionalized macrocycles for selective recognition of other species is of great interest to chemists. Many functionalized macrocycles have been synthesized and employed to develop fluorescent sensors (Tong et al., 2000). 2,5-Diaryl-1,3,4-oxadizole forms chiral macrocyclic phosphoramidate receptors with phosphorus oxychloride, and their crystal structures have been reported (Du, Hua & Jin, 2001). As part of an investigation of the potential recognition properties of macrocycles, we now reported the synthesis and structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The oxadizole ring (O1/C1/N1/N2/C18) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0017 Å. It makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, respectively, with the benzene rings (C2—C7), (C12—C17) and (C19—C24). The crystal packing is stabilized by weak non-classical intermolecular C—H···O hydrogen bonds which link the molecules into an infinite network. The bond lengths and angles in (I) are within their normal ranges (Du, Hua, Wang & Yan 2001).

Experimental

2,5-Di(o-hydroxyphenyl)-1,3,4-oxadiazole (0.8 g, 3.0 mmol), K₂CO₃ (1.4 g, 10 mmol) and tri-(p-phenylsulfonyl) diethanol amine (2.3 g, 4 mmol) were added and dissolved in 50 ml of DMF and the mixture was stirred at 413 K for 20 h giving a colourless precipitate. The product was isolated, recrystallized from ethyl acetate then dried in a vacuum to give the pure compound in 65% yield. colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of ethyl acetate.