catena-Poly[[di-μ-bromido-dicopper(I)]bis-[μ-η,σ-4-(2-allyl-2H-tetra-zol-5-yl)pyridine]].

The title compound, [CuBr(C(9)H(9)N(5))](n), prepared by the solvothermal treatment of CuBr with 4-(2-allyl-2H-tetra-zol-5-yl)pyridine, is a new homometallic Cu(I)-olefin coordination polymer in which dinuclear Cu(2)Br(2) units are linked by the organic olefin ligand 4-(2-allyl-2H-tetra-zol-5-yl)pyridine, which acts as a bidentate ligand connecting two neighbouring Cu(2)Br(2) units through the pyridine N atom and the double bond of the allyl group. The coordination of Cu(I) is slightly distorted tetrahedral.

Related literature

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

Experimental

Crystal data

[CuBr(C9H9N5)]

M = 330.66

Monoclinic,

a = 17.502 (3) Å

b = 12.047 (2) Å

c = 13.664 (3) Å

β = 129.52 (3)°

V = 2222.4 (12) Å3

Z = 8

Mo Kα radiation

μ = 5.54 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 = 0.661, T max = 1 (expected range = 0.380–0.575)

11222 measured reflections

2552 independent reflections

1962 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.088

S = 1.07

2552 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.77 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: ORTEPIII (Johnson & Burnett, 1997 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012439/dn2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012439/dn2345Isup2.hkl

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

[CuBr(C9H9N5)]	F(000) = 1296
Mr = 330.66	Dx = 1.977 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10074 reflections
a = 17.502 (3) Å	θ = 3.0–28.8°
b = 12.047 (2) Å	µ = 5.54 mm−1
c = 13.664 (3) Å	T = 293 K
β = 129.52 (3)°	Block, colorless
V = 2222.4 (12) Å3	0.2 × 0.15 × 0.1 mm
Z = 8

Rigaku Mercury2 diffractometer	2552 independent reflections
Radiation source: fine-focus sealed tube	1962 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.661, Tmax = 1	l = −17→17
11222 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.03P)2 + 4.1679P] where P = (Fo2 + 2Fc2)/3
2552 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.77 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
Cu1	0.39530 (4)	−0.00789 (3)	0.59335 (4)	0.03898 (15)
Br1	0.41669 (3)	−0.00735 (3)	0.79367 (3)	0.03492 (12)
N1	0.4034 (2)	0.4106 (2)	0.5433 (3)	0.0379 (8)
N2	0.3650 (3)	0.4582 (3)	0.3597 (3)	0.0448 (8)
N3	0.3835 (3)	0.3508 (3)	0.3743 (3)	0.0475 (9)
N4	0.4055 (2)	0.3250 (2)	0.4833 (3)	0.0363 (7)
N5	0.3645 (2)	0.8317 (2)	0.5386 (3)	0.0319 (7)
C1	0.2905 (3)	0.0849 (3)	0.4367 (4)	0.0397 (9)
H1A	0.2909	0.0807	0.3661	0.048*
H1B	0.2243	0.0836	0.4105	0.048*
C2	0.3548 (3)	0.1574 (3)	0.5299 (4)	0.0376 (9)
H2	0.3295	0.2001	0.5648	0.045*
C3	0.4350 (3)	0.2120 (3)	0.5368 (4)	0.0449 (10)
H3A	0.4950	0.2157	0.6246	0.054*
H3B	0.4488	0.1681	0.4902	0.054*
C4	0.3456 (3)	0.6920 (3)	0.4013 (3)	0.0356 (9)
H4	0.3317	0.6742	0.3251	0.043*
C5	0.3673 (2)	0.6090 (3)	0.4859 (3)	0.0285 (7)
C6	0.3807 (3)	0.7513 (3)	0.6168 (3)	0.0338 (8)
H6	0.3909	0.7711	0.6901	0.041*
C7	0.3451 (3)	0.8007 (3)	0.4310 (3)	0.0366 (9)
H7	0.3304	0.8554	0.3732	0.044*
C8	0.3830 (3)	0.6403 (3)	0.5945 (3)	0.0338 (8)
H8	0.3951	0.5871	0.6522	0.041*
C9	0.3769 (3)	0.4926 (3)	0.4619 (3)	0.0315 (8)

	U11	U22	U33	U12	U13	U23
Cu1	0.0551 (3)	0.0158 (2)	0.0379 (3)	0.0008 (2)	0.0258 (2)	−0.00052 (17)
Br1	0.0433 (2)	0.0305 (2)	0.0396 (2)	−0.00627 (16)	0.03041 (19)	−0.00676 (15)
N1	0.0484 (19)	0.0190 (15)	0.0431 (19)	0.0017 (14)	0.0276 (17)	0.0017 (13)
N2	0.062 (2)	0.0236 (16)	0.043 (2)	0.0066 (16)	0.0307 (18)	0.0007 (14)
N3	0.068 (2)	0.0244 (17)	0.048 (2)	0.0036 (16)	0.036 (2)	−0.0030 (14)
N4	0.0409 (18)	0.0135 (14)	0.050 (2)	0.0011 (13)	0.0271 (17)	−0.0007 (13)
N5	0.0372 (17)	0.0154 (14)	0.0352 (17)	0.0002 (12)	0.0193 (15)	−0.0010 (12)
C1	0.039 (2)	0.0268 (19)	0.048 (2)	0.0042 (16)	0.0248 (19)	0.0102 (17)
C2	0.057 (2)	0.0164 (17)	0.047 (2)	0.0117 (17)	0.037 (2)	0.0068 (15)
C3	0.044 (2)	0.0163 (18)	0.064 (3)	0.0055 (16)	0.029 (2)	0.0065 (17)
C4	0.051 (2)	0.0209 (17)	0.031 (2)	−0.0029 (16)	0.0243 (19)	−0.0024 (14)
C5	0.0269 (17)	0.0171 (16)	0.0332 (18)	−0.0031 (14)	0.0153 (16)	−0.0011 (13)
C6	0.045 (2)	0.0199 (17)	0.038 (2)	−0.0036 (15)	0.0272 (19)	−0.0026 (15)
C7	0.049 (2)	0.0185 (17)	0.037 (2)	0.0002 (16)	0.0248 (19)	0.0047 (15)
C8	0.042 (2)	0.0199 (17)	0.036 (2)	−0.0025 (15)	0.0236 (18)	0.0034 (14)
C9	0.0322 (17)	0.0168 (17)	0.0372 (19)	−0.0029 (14)	0.0182 (16)	0.0003 (14)

Cu1—N5i	2.017 (3)	C1—H1A	0.9700
Cu1—C1	2.050 (4)	C1—H1B	0.9700
Cu1—C2	2.106 (3)	C2—C3	1.496 (6)
Cu1—Br1	2.5156 (9)	C2—H2	0.9800
Cu1—Br1ii	2.5973 (11)	C3—H3A	0.9700
Br1—Cu1ii	2.5973 (11)	C3—H3B	0.9700
N1—C9	1.330 (4)	C4—C7	1.373 (5)
N1—N4	1.332 (4)	C4—C5	1.386 (5)
N2—N3	1.317 (4)	C4—H4	0.9300
N2—C9	1.340 (5)	C5—C8	1.378 (5)
N3—N4	1.317 (5)	C5—C9	1.475 (4)
N4—C3	1.475 (4)	C6—C8	1.378 (5)
N5—C6	1.332 (4)	C6—H6	0.9300
N5—C7	1.334 (4)	C7—H7	0.9300
N5—Cu1iii	2.017 (3)	C8—H8	0.9300
C1—C2	1.351 (5)
N5i—Cu1—C1	106.55 (13)	C3—C2—Cu1	109.5 (2)
N5i—Cu1—C2	144.30 (14)	C1—C2—H2	115.7
C1—Cu1—C2	37.93 (14)	C3—C2—H2	115.7
N5i—Cu1—Br1	103.04 (9)	Cu1—C2—H2	115.7
C1—Cu1—Br1	123.33 (12)	N4—C3—C2	110.9 (3)
C2—Cu1—Br1	102.94 (10)	N4—C3—H3A	109.5
N5i—Cu1—Br1ii	99.28 (9)	C2—C3—H3A	109.5
C1—Cu1—Br1ii	124.96 (11)	N4—C3—H3B	109.5
C2—Cu1—Br1ii	102.07 (11)	C2—C3—H3B	109.5
Br1—Cu1—Br1ii	95.64 (4)	H3A—C3—H3B	108.0
Cu1—Br1—Cu1ii	84.36 (4)	C7—C4—C5	119.4 (3)
C9—N1—N4	101.0 (3)	C7—C4—H4	120.3
N3—N2—C9	106.6 (3)	C5—C4—H4	120.3
N4—N3—N2	105.6 (3)	C8—C5—C4	117.6 (3)
N3—N4—N1	114.3 (3)	C8—C5—C9	121.8 (3)
N3—N4—C3	122.5 (3)	C4—C5—C9	120.6 (3)
N1—N4—C3	123.2 (3)	N5—C6—C8	123.3 (3)
C6—N5—C7	117.1 (3)	N5—C6—H6	118.3
C6—N5—Cu1iii	121.9 (2)	C8—C6—H6	118.3
C7—N5—Cu1iii	119.8 (2)	N5—C7—C4	123.2 (3)
C2—C1—Cu1	73.3 (2)	N5—C7—H7	118.4
C2—C1—H1A	116.2	C4—C7—H7	118.4
Cu1—C1—H1A	116.2	C6—C8—C5	119.3 (3)
C2—C1—H1B	116.2	C6—C8—H8	120.3
Cu1—C1—H1B	116.2	C5—C8—H8	120.3
H1A—C1—H1B	113.2	N1—C9—N2	112.5 (3)
C1—C2—C3	122.0 (4)	N1—C9—C5	123.2 (3)
C1—C2—Cu1	68.8 (2)	N2—C9—C5	124.2 (3)