1-(3-Bromo-prop-yl)-4-(2-pyrid-yl)-1H-1,2,3-triazole.

In the structure of the title compound, C(10)H(11)BrN(4), 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-H⋯N inter-actions. There are two mol-ecules in the unit cell, which form a centrosymmetric head-to-tail dimer. The dimers are stabilized through π-π inter-actions [centroid-centroid distance = 3.733 (4) Å and mean inter-planar distance = 3.806 (12) Å] between the substituted 1,2,3-triazole ring and the pyridine rings in adjacent mol-ecules. Each dimer inter-acts with two neighbouring dimers above and below, forming a slipped stack of dimers through the crystal. The 3-bromo-propyl chain sits over the pyridine ring of a neighbouring mol-ecule and the triazole rings of nearby mol-ecules are adjacent.

Related literature

For details of the Cu(I)-catalysed 1,3-cyclo­addition of organic n class="Chemical">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 = 267.14

Triclinic,

a = 5.658 (2) Å

b = 9.688 (4) Å

c = 10.191 (4) Å

α = 84.498 (3)°

β = 85.663 (2)°

γ = 83.854 (2)°

V = 551.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.071

S = 0.97

1879 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012148/fj2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012148/fj2204Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H11BrN4	Z = 2
Mr = 267.14	F(000) = 268
Triclinic, P1	Dx = 1.608 Mg m−3
Hall symbol: -P 1	Melting point: 362 K
a = 5.658 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.688 (4) Å	Cell parameters from 5048 reflections
c = 10.191 (4) Å	θ = 3.1–33.3°
α = 84.498 (3)°	µ = 3.70 mm−1
β = 85.663 (2)°	T = 90 K
γ = 83.854 (2)°	Irregular, colourless
V = 551.6 (4) Å3	0.53 × 0.23 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	1879 independent reflections
Radiation source: fine-focus sealed tube	1759 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.358, Tmax = 0.66	k = −11→11
8776 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.5592P] where P = (Fo2 + 2Fc2)/3
1879 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.84285 (5)	−0.19395 (3)	0.97535 (3)	0.03839 (13)
N3	0.3211 (3)	0.1602 (2)	0.6731 (2)	0.0243 (4)
C6	0.4287 (4)	0.2879 (2)	0.4946 (2)	0.0177 (5)
N2	0.2396 (4)	0.2401 (2)	0.5713 (2)	0.0236 (4)
N1	0.6005 (4)	0.4000 (2)	0.2965 (2)	0.0230 (4)
N4	0.5611 (3)	0.15753 (19)	0.66118 (19)	0.0188 (4)
C5	0.3999 (4)	0.3838 (2)	0.3747 (2)	0.0179 (5)
C7	0.6350 (4)	0.2341 (2)	0.5518 (2)	0.0185 (5)
H7	0.7908	0.2476	0.5215	0.022*
C4	0.1805 (4)	0.4545 (2)	0.3468 (2)	0.0216 (5)
H4	0.0447	0.4385	0.4010	0.026*
C8	0.7073 (4)	0.0790 (2)	0.7608 (2)	0.0212 (5)
H8A	0.6075	0.0576	0.8403	0.025*
H8B	0.8267	0.1360	0.7832	0.025*
C2	0.3717 (5)	0.5674 (2)	0.1552 (2)	0.0244 (5)
H2	0.3677	0.6302	0.0802	0.029*
C1	0.5814 (4)	0.4892 (2)	0.1884 (2)	0.0249 (5)
H1	0.7170	0.4993	0.1322	0.030*
C9	0.8298 (5)	−0.0555 (3)	0.7124 (2)	0.0291 (6)
H9A	0.7101	−0.1168	0.7002	0.035*
H9B	0.9133	−0.0349	0.6273	0.035*
C3	0.1681 (4)	0.5495 (2)	0.2364 (2)	0.0242 (5)
H3	0.0245	0.6008	0.2172	0.029*
C10	1.0035 (5)	−0.1294 (3)	0.8062 (3)	0.0309 (6)
H10A	1.1188	−0.0667	0.8222	0.037*
H10B	1.0890	−0.2087	0.7663	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.04089 (19)	0.03674 (19)	0.03195 (18)	0.00206 (12)	0.00069 (13)	0.01657 (12)
N3	0.0180 (10)	0.0273 (11)	0.0260 (11)	−0.0011 (8)	−0.0002 (9)	0.0033 (9)
C6	0.0187 (11)	0.0154 (10)	0.0191 (11)	−0.0011 (9)	−0.0003 (9)	−0.0032 (9)
N2	0.0191 (10)	0.0265 (10)	0.0241 (11)	−0.0024 (8)	−0.0010 (8)	0.0032 (9)
N1	0.0214 (10)	0.0240 (10)	0.0227 (10)	−0.0008 (8)	0.0001 (9)	−0.0013 (8)
N4	0.0171 (9)	0.0191 (9)	0.0194 (10)	0.0001 (8)	−0.0017 (8)	0.0001 (8)
C5	0.0187 (11)	0.0152 (10)	0.0200 (11)	−0.0024 (9)	−0.0012 (9)	−0.0028 (9)
C7	0.0159 (11)	0.0181 (10)	0.0212 (11)	−0.0013 (9)	−0.0002 (9)	−0.0014 (9)
C4	0.0170 (11)	0.0229 (11)	0.0246 (12)	−0.0011 (9)	−0.0006 (10)	−0.0021 (10)
C8	0.0240 (12)	0.0200 (11)	0.0187 (11)	0.0020 (9)	−0.0037 (10)	−0.0007 (9)
C2	0.0344 (14)	0.0183 (11)	0.0208 (12)	−0.0028 (10)	−0.0075 (11)	0.0015 (9)
C1	0.0251 (12)	0.0266 (12)	0.0220 (12)	−0.0039 (10)	0.0024 (10)	0.0015 (10)
C9	0.0424 (15)	0.0230 (12)	0.0198 (12)	0.0072 (11)	−0.0026 (11)	−0.0027 (10)
C3	0.0239 (12)	0.0204 (11)	0.0281 (13)	0.0029 (10)	−0.0067 (11)	−0.0030 (10)
C10	0.0357 (15)	0.0261 (13)	0.0264 (13)	0.0093 (11)	0.0030 (12)	0.0028 (10)

Br1—C10	1.966 (3)	C8—C9	1.516 (3)
N3—N2	1.315 (3)	C8—H8A	0.9700
N3—N4	1.352 (3)	C8—H8B	0.9700
C6—N2	1.371 (3)	C2—C3	1.383 (4)
C6—C7	1.373 (3)	C2—C1	1.384 (4)
C6—C5	1.471 (3)	C2—H2	0.9300
N1—C1	1.337 (3)	C1—H1	0.9300
N1—C5	1.351 (3)	C9—C10	1.501 (4)
N4—C7	1.344 (3)	C9—H9A	0.9700
N4—C8	1.463 (3)	C9—H9B	0.9700
C5—C4	1.388 (3)	C3—H3	0.9300
C7—H7	0.9300	C10—H10A	0.9700
C4—C3	1.384 (3)	C10—H10B	0.9700
C4—H4	0.9300
N2—N3—N4	106.83 (18)	H8A—C8—H8B	107.9
N2—C6—C7	108.4 (2)	C3—C2—C1	118.2 (2)
N2—C6—C5	122.9 (2)	C3—C2—H2	120.9
C7—C6—C5	128.7 (2)	C1—C2—H2	120.9
N3—N2—C6	108.78 (19)	N1—C1—C2	123.8 (2)
C1—N1—C5	117.1 (2)	N1—C1—H1	118.1
C7—N4—N3	111.53 (18)	C2—C1—H1	118.1
C7—N4—C8	127.7 (2)	C10—C9—C8	112.8 (2)
N3—N4—C8	120.73 (19)	C10—C9—H9A	109.0
N1—C5—C4	122.9 (2)	C8—C9—H9A	109.0
N1—C5—C6	115.7 (2)	C10—C9—H9B	109.0
C4—C5—C6	121.4 (2)	C8—C9—H9B	109.0
N4—C7—C6	104.5 (2)	H9A—C9—H9B	107.8
N4—C7—H7	127.8	C2—C3—C4	119.3 (2)
C6—C7—H7	127.8	C2—C3—H3	120.4
C3—C4—C5	118.6 (2)	C4—C3—H3	120.4
C3—C4—H4	120.7	C9—C10—Br1	111.7 (2)
C5—C4—H4	120.7	C9—C10—H10A	109.3
N4—C8—C9	111.80 (19)	Br1—C10—H10A	109.3
N4—C8—H8A	109.3	C9—C10—H10B	109.3
C9—C8—H8A	109.3	Br1—C10—H10B	109.3
N4—C8—H8B	109.3	H10A—C10—H10B	107.9
C9—C8—H8B	109.3

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N2i	0.93	2.62	3.449 (4)	149
C10—H10B···N1ii	0.97	2.51	3.450 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N2i	0.93	2.62	3.449 (4)	149
C10—H10B⋯N1ii	0.97	2.51	3.450 (4)	164

Symmetry codes: (i) ; (ii) .