catena-Poly[[bromidocopper(I)]-μ-η,σ-3-(2-allyl-2H-tetra-zol-5-yl)pyridine].

The title compound, [CuBr(C(9)H(9)N(5))](n), has been prepared by the solvothermal treatment of CuBr with 3-(2-allyl-2H-tetra-zol-5-yl)pyridine. It is a new homometallic Cu(I) olefin coord-ination polymer in which the Cu(I) atoms are linked by the 3-(2-allyl-2H-tetra-zol-5-yl)pyridine ligands and bonded to one terminal Br atom each. The organic ligand acts as a bidentate ligand connecting two neighboring Cu centers through the N atom of the pyridine ring and the double bond of the allyl group. A three-dimensional structure is formed through weak Cu-Br [3.1579 (8) Å], C-H⋯Br and C-H⋯N inter-actions.

Related literature

For the solvothermal synthesis and related structures, see: Ye et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

[CuBr(C9H9N5)]

M = 330.66

Triclinic,

a = 7.4464 (15) Å

b = 7.7982 (16) Å

c = 9.940 (2) Å

α = 80.15 (3)°

β = 76.02 (3)°

γ = 85.13 (3)°

V = 551.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.58 mm−1

T = 293 (2) K

0.2 × 0.15 × 0.1 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.720, T max = 1 (expected range = 0.412–0.572)

5748 measured reflections

2522 independent reflections

2173 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.072

S = 1.11

2522 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and CAMERON (Pearce et al., 2000 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010313/dn2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010313/dn2335Isup2.hkl

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

[CuBr(C9H9N5)]	Z = 2
Mr = 330.66	F(000) = 324
Triclinic, P1	Dx = 1.992 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4464 (15) Å	Cell parameters from 5524 reflections
b = 7.7982 (16) Å	θ = 3.1–28.8°
c = 9.940 (2) Å	µ = 5.58 mm−1
α = 80.15 (3)°	T = 293 K
β = 76.02 (3)°	Block, colorless
γ = 85.13 (3)°	0.2 × 0.15 × 0.1 mm
V = 551.3 (2) Å3

Rigaku Mercury2 diffractometer	2522 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.720, Tmax = 1	l = −12→12
5748 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0241P)2 + 0.2889P] where P = (Fo2 + 2Fc2)/3
2522 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.16126 (4)	0.38319 (4)	0.41251 (3)	0.03175 (10)
Cu1	0.16354 (5)	0.33917 (5)	0.39002 (4)	0.03347 (12)
N1	0.2917 (3)	0.5093 (3)	0.2281 (2)	0.0267 (5)
N2	0.0895 (4)	0.9916 (3)	−0.2237 (2)	0.0269 (5)
N3	0.2398 (4)	0.9414 (3)	−0.1753 (2)	0.0282 (5)
N4	−0.0584 (4)	0.9032 (4)	−0.1582 (3)	0.0357 (6)
N5	−0.0058 (4)	0.7876 (4)	−0.0601 (3)	0.0344 (6)
C1	0.4652 (4)	0.5523 (4)	0.2192 (3)	0.0346 (7)
H1	0.5264	0.4971	0.2872	0.042*
C2	0.5561 (5)	0.6741 (5)	0.1144 (4)	0.0380 (8)
H2	0.6777	0.6985	0.1099	0.046*
C3	0.4632 (4)	0.7608 (4)	0.0144 (3)	0.0325 (7)
H3	0.5213	0.8450	−0.0573	0.039*
C4	0.2039 (4)	0.5909 (4)	0.1310 (3)	0.0251 (6)
H4	0.0844	0.5603	0.1355	0.030*
C5	0.2839 (4)	0.7195 (4)	0.0238 (3)	0.0244 (6)
C6	0.1752 (4)	0.8133 (4)	−0.0724 (3)	0.0256 (6)
C8	0.0820 (5)	1.1435 (4)	−0.3331 (3)	0.0311 (7)
H8A	0.1252	1.2437	−0.3063	0.037*
H8B	−0.0457	1.1694	−0.3395	0.037*
C7	0.1968 (4)	0.1148 (4)	0.5261 (3)	0.0275 (6)
H7	0.1777	0.0060	0.4956	0.033*
C9	0.3637 (4)	0.1859 (4)	0.4666 (4)	0.0377 (8)
H9A	0.4502	0.1221	0.4010	0.045*
H9B	0.4217	0.2348	0.5280	0.045*

	U11	U22	U33	U12	U13	U23
Br1	0.02503 (17)	0.03096 (17)	0.03858 (18)	−0.00123 (12)	−0.01088 (13)	0.00150 (13)
Cu1	0.0248 (2)	0.0368 (2)	0.0298 (2)	0.00004 (16)	−0.00487 (16)	0.01707 (17)
N1	0.0230 (13)	0.0300 (13)	0.0224 (12)	0.0013 (10)	−0.0036 (10)	0.0059 (10)
N2	0.0302 (13)	0.0260 (12)	0.0209 (11)	−0.0013 (10)	−0.0060 (10)	0.0063 (10)
N3	0.0328 (14)	0.0269 (13)	0.0206 (11)	−0.0037 (10)	−0.0046 (10)	0.0065 (10)
N4	0.0316 (15)	0.0371 (15)	0.0316 (14)	−0.0044 (12)	−0.0035 (12)	0.0096 (12)
N5	0.0296 (14)	0.0376 (15)	0.0295 (13)	−0.0074 (11)	−0.0056 (11)	0.0140 (12)
C1	0.0295 (17)	0.0415 (18)	0.0306 (16)	−0.0001 (14)	−0.0104 (13)	0.0048 (14)
C2	0.0269 (17)	0.0453 (19)	0.0396 (18)	−0.0110 (14)	−0.0080 (14)	0.0048 (15)
C3	0.0337 (17)	0.0300 (16)	0.0296 (15)	−0.0072 (13)	−0.0048 (13)	0.0065 (13)
C4	0.0240 (15)	0.0265 (14)	0.0209 (13)	−0.0017 (12)	−0.0028 (11)	0.0040 (11)
C5	0.0273 (15)	0.0246 (14)	0.0187 (13)	−0.0004 (12)	−0.0033 (11)	0.0006 (11)
C6	0.0307 (16)	0.0242 (14)	0.0185 (13)	−0.0028 (12)	−0.0020 (12)	0.0014 (11)
C8	0.0387 (18)	0.0250 (15)	0.0246 (14)	0.0021 (13)	−0.0069 (13)	0.0075 (12)
C7	0.0307 (16)	0.0217 (14)	0.0258 (14)	0.0031 (12)	−0.0078 (12)	0.0075 (12)
C9	0.0286 (17)	0.0375 (18)	0.0389 (18)	0.0074 (14)	−0.0084 (14)	0.0130 (15)

Br1—Cu1	2.3752 (7)	C2—H2	0.9300
Cu1—N1	2.001 (2)	C3—C5	1.377 (4)
Cu1—C9	2.040 (3)	C3—H3	0.9300
Cu1—C7	2.057 (3)	C4—C5	1.387 (4)
N1—C4	1.337 (3)	C4—H4	0.9300
N1—C1	1.341 (4)	C5—C6	1.463 (4)
N2—N4	1.320 (3)	C8—C7i	1.495 (4)
N2—N3	1.326 (3)	C8—H8A	0.9700
N2—C8	1.472 (3)	C8—H8B	0.9700
N3—C6	1.330 (4)	C7—C9	1.361 (4)
N4—N5	1.320 (4)	C7—C8ii	1.495 (4)
N5—C6	1.353 (4)	C7—H7	0.9800
C1—C2	1.370 (4)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.395 (4)
N1—Cu1—C9	107.38 (12)	C5—C4—H4	118.7
N1—Cu1—C7	145.02 (11)	C3—C5—C4	118.6 (3)
C9—Cu1—C7	38.80 (12)	C3—C5—C6	121.4 (3)
N1—Cu1—Br1	108.50 (7)	C4—C5—C6	119.9 (3)
C9—Cu1—Br1	144.01 (9)	N3—C6—N5	112.7 (3)
C7—Cu1—Br1	105.36 (9)	N3—C6—C5	123.6 (3)
C4—N1—C1	118.2 (3)	N5—C6—C5	123.5 (3)
C4—N1—Cu1	121.3 (2)	N2—C8—C7i	112.7 (2)
C1—N1—Cu1	120.37 (19)	N2—C8—H8A	109.1
N4—N2—N3	114.7 (2)	C7i—C8—H8A	109.1
N4—N2—C8	122.0 (3)	N2—C8—H8B	109.1
N3—N2—C8	123.1 (2)	C7i—C8—H8B	109.1
N2—N3—C6	101.0 (2)	H8A—C8—H8B	107.8
N2—N4—N5	105.8 (2)	C9—C7—C8ii	123.7 (3)
N4—N5—C6	105.9 (2)	C9—C7—Cu1	69.93 (17)
N1—C1—C2	122.8 (3)	C8ii—C7—Cu1	106.21 (19)
N1—C1—H1	118.6	C9—C7—H7	115.6
C2—C1—H1	118.6	C8ii—C7—H7	115.6
C1—C2—C3	118.9 (3)	Cu1—C7—H7	115.6
C1—C2—H2	120.6	C7—C9—Cu1	71.26 (18)
C3—C2—H2	120.6	C7—C9—H9A	116.5
C5—C3—C2	118.8 (3)	Cu1—C9—H9A	116.5
C5—C3—H3	120.6	C7—C9—H9B	116.5
C2—C3—H3	120.6	Cu1—C9—H9B	116.5
N1—C4—C5	122.7 (3)	H9A—C9—H9B	113.5
N1—C4—H4	118.7

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1iii	0.93	2.90	3.776 (3)	157.
C2—H2···N5iii	0.93	2.62	3.415 (4)	144.
C9—H9A···N3iv	0.97	2.88	3.800 (4)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1i	0.93	2.90	3.776 (3)	157
C2—H2⋯N5i	0.93	2.62	3.415 (4)	144
C9—H9A⋯N3ii	0.97	2.88	3.800 (4)	159

Symmetry codes: (i) ; (ii) .