1-[(5-Bromo­pent­yloxy)meth­yl]pyrene

Xixi Bian; Tongjiang Cai; Jin Zhou; Qin Huang; Xunwen Xiao

doi:10.1107/S1600536811018253

. 2011 May 20;67(Pt 6):o1456. doi: 10.1107/S1600536811018253

1-[(5-Bromopentyloxy)methyl]pyrene

Xixi Bian ^a, Tongjiang Cai ^a, Jin Zhou ^a, Qin Huang ^a, Xunwen Xiao ^a,^*

PMCID: PMC3120293 PMID: 21754829

Abstract

In the title compound, C₂₂H₂₁BrO, other than the Br atom, the non-H atoms are approximately co-planar [maxium deviation = 0.178 (2) Å] and the alkoxy chain shows an all-anti conformation. A weak intermolecular C—H⋯Br hydrogen bond contributes to the stabilization of the crystal structure.

Related literature

For the synthesis of pyrene derivatives, see Filby & Steed (2006 ▶). For the use of pyrenes as fluorescence sensors, see: Bell & Hext (2004 ▶). For related structures, see: Fun et al. (2009 ▶); Gruber et al. (2010 ▶); Xiao et al. (2005 ▶).

Experimental

Crystal data

C₂₂H₂₁BrO
M _r = 381.30
Triclinic,
a = 7.417 (2) Å
b = 7.4817 (16) Å
c = 17.545 (5) Å
α = 79.924 (19)°
β = 88.90 (2)°
γ = 64.295 (12)°
V = 861.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.39 mm⁻¹
T = 223 K
0.45 × 0.40 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.373, T _max = 0.616
7097 measured reflections
3085 independent reflections
2399 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.047
S = 0.88
3085 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018253/ng5165sup1.cif

e-67-o1456-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018253/ng5165Isup2.hkl

e-67-o1456-Isup2.hkl^{(151.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018253/ng5165Isup3.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
C6—H6⋯Br1ⁱ	0.94	3.02	3.869 (2)	151

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the NNS (20902051), the Education Committee of Zhejiang Province (Z200906833), Ningbo Natural Science (2010 A610186) and the Ministry of Education Scientific Research Foundation for Returned Overseas Scholars.

supplementary crystallographic information

Comment

As a fluorogenic unit, pyrene is one of the most useful fluorescene probe because of its relatively efficient excimer formation and emission. In this respect, the title compound was prepared as part of our research on the solid state structure of fluorogenic tetrathiafulvalene with possible molecular switch (Xiao et al.., 2005).

The bond lengths and bond angles of the title compound are found to have norml values (Fun et al.., 2009 Gruber et al.., 2010). Expect the Br atom and H atoms, the molecule is essentially planar with the maximum deviation from planarity being 0.1781 (21) Å. In the substitute alkoxy chain, expect the Br atom, it shows the typical all-anti conformation (Fig.1).

The crystal packing is stabilized by C—H···Br intermolecular hydrogen bonding (table.1) (Fig.2).

Experimental

The title compound was synthesiaed according to a literature procedure (Xiao et al.., 2005). Slow evaporation of a solution in THF gave single crystals suitable for X–ray analysis.