1-(3-Bromo­prop­yl)-4-(2-pyrid­yl)-1H-1,2,3-triazole

Crowley, J.D.; Bandeen, P.H.; Hanton, L.R.

doi:10.1107/S1600536809012148

Volume 65
Part 5
Pages o999-o1000
May 2009

Received 20 March 2009
Accepted 1 April 2009
Online 8 April 2009

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 13.8
Details

1-(3-Bromopropyl)-4-(2-pyridyl)-1H-1,2,3-triazole

James D. Crowley,^a ^* Pauline H. Bandeen ^a and Lyall R. Hanton ^a

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
Correspondence e-mail: jcrowley@chemistry.otago.ac.nz

In the structure of the title compound, C₁₀H₁₁BrN₄, the plane of the substituted 1,2,3-triazole ring is tilted by 14.84 (10)° with respect to the mean plane of the pyridine ring. The pyridine and closest triazole N atoms adopt an anti arrangement which removes any lone pair-lone pair repulsions between the N atoms. This conformation is further stabilized by weak intermolecular C-HN interactions. There are two molecules in the unit cell, which form a centrosymmetric head-to-tail dimer. The dimers are stabilized through [pi] - [pi] interactions [centroid-centroid distance = 3.733 (4) Å and mean interplanar distance = 3.806 (12) Å] between the substituted 1,2,3-triazole ring and the pyridine rings in adjacent molecules. Each dimer interacts with two neighbouring dimers above and below, forming a slipped stack of dimers through the crystal. The 3-bromopropyl chain sits over the pyridine ring of a neighbouring molecule and the triazole rings of nearby molecules are adjacent.

Related literature

For details of the Cu(I)-catalysed 1,3-cycloaddition of organic azides with terminal alkynes, see: Rostovtsev et al. (2002); Tornoe et al. (2002); Meldal & Tornoe (2008). For applications of pyridyl-functionalized 1,2,3-triazoles, see: Li & Flood (2008); Meudtner & Hecht (2008); Krivopalov & Shkurko (2005); Li et al. (2007); Richardson et al. (2008). For related structures, see Schweinfurth et al. (2008); Obata et al. (2008).

Experimental

Crystal data

C₁₀H₁₁BrN₄
M_r = 267.14
Triclinic, $[P \overline 1]$
a = 5.658 (2) Å
b = 9.688 (4) Å
c = 10.191 (4) Å
= 84.498 (3)°
= 85.663 (2)°
= 83.854 (2)°
V = 551.6 (4) Å³
Z = 2
Mo K radiation
= 3.70 mm^-1
T = 90 K
0.53 × 0.23 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.358, T_max = 0.66
8776 measured reflections
1879 independent reflections
1759 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.071
S = 0.97
1879 reflections
136 parameters
H-atom parameters constrained
_max = 0.64 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7N2ⁱ	0.93	2.62	3.449 (4)	149
C10-H10BN1ⁱⁱ	0.97	2.51	3.450 (4)	164
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2204 ).

Acknowledgements

We thank the Chemistry Department, University of Otago, for financial assistance.

References

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organic compounds