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

The title polymer, [Cu(2)Cl(2)(C(9)H(9)N(5))(2)](n), has been prepared by the solvothermal treatment of CuCl with 4-(2-allyl-2H-tetra-zol-5-yl)pyridine. The crystal structure shows that the title compound is a homometallic Cu(I)-olefin coordination polymer, in which the Cu(2)Cl(2) nodes are bridged by two olefin ligands. The asymmetric unit contains one-half of the monomer, the complete monomer having twofold rotation symmetry. The coordination environment of Cu(I) is slightly distorted tetra-hedral, with coordination sites being two μ(2)-Cl atoms, one pyridine N atom of an organic ligand and one allylic double bond of a symmetry-related ligand. Each organic mol-ecule behaves as a bidentate ligand, connecting two neighboring Cu(2)Cl(2) dimers in the polymeric chain, which runs along [010].

Related literature

For the solvothermal synthesis and for related structures, see: Ye et al. (2005 ▶, 2007 ▶). For related structures, see: Wang (2008a,b,c).

Experimental

Crystal data

[Cu2Cl2(C9H9N5)2]

M = 286.21

Monoclinic,

a = 17.270 (3) Å

b = 12.040 (2) Å

c = 13.064 (3) Å

β = 127.94 (3)°

V = 2142.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 2.27 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 = 0.643, T max = 0.800

10753 measured reflections

2451 independent reflections

1814 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.06

2451 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.39 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 XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017820/bh2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017820/bh2171Isup2.hkl

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

[Cu2Cl2(C9H9N5)2]	F(000) = 1152
Mr = 286.21	Dx = 1.775 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9724 reflections
a = 17.270 (3) Å	θ = 3.2–28.8°
b = 12.040 (2) Å	µ = 2.27 mm−1
c = 13.064 (3) Å	T = 293 K
β = 127.94 (3)°	Block, colourless
V = 2142.3 (7) Å3	0.2 × 0.15 × 0.1 mm
Z = 8

Rigaku Mercury2 diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	1814 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD_Profile_fitting scans	h = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.643, Tmax = 0.800	l = −16→16
10753 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.6044P] where P = (Fo2 + 2Fc2)/3
2451 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.39314 (3)	0.49203 (3)	0.59806 (4)	0.03726 (16)
Cl1	0.57394 (6)	0.49142 (6)	0.69868 (8)	0.0343 (2)
N1	0.3855 (2)	0.8479 (2)	0.3785 (3)	0.0460 (7)
N2	0.40548 (19)	0.91092 (19)	0.5524 (3)	0.0362 (6)
N3	0.3659 (2)	0.9552 (2)	0.3613 (3)	0.0435 (7)
N4	0.40899 (19)	0.82409 (19)	0.4924 (3)	0.0345 (6)
N5	0.36588 (18)	0.33219 (19)	0.5431 (2)	0.0304 (6)
C1	0.2946 (2)	0.5831 (2)	0.4346 (3)	0.0388 (8)
H1A	0.2411	0.5472	0.4259	0.068 (12)*
H1C	0.3062	0.5683	0.3729	0.052 (11)*
C2	0.3534 (2)	0.6549 (2)	0.5330 (3)	0.0350 (7)
H2A	0.3419	0.6698	0.5948	0.089 (15)*
C3	0.4367 (2)	0.7121 (2)	0.5475 (3)	0.0402 (8)
H3A	0.4545	0.6695	0.5027	0.030 (8)*
H3B	0.4928	0.7163	0.6374	0.052 (11)*
C4	0.3685 (2)	0.1086 (2)	0.4905 (3)	0.0273 (6)
C5	0.3489 (2)	0.2998 (2)	0.4331 (3)	0.0345 (7)
H5A	0.3356	0.3559	0.3720	0.041 (9)*
C6	0.3829 (2)	0.1409 (2)	0.6025 (3)	0.0321 (7)
H6A	0.3937	0.0860	0.6633	0.047 (10)*
C7	0.3811 (2)	0.2523 (2)	0.6256 (3)	0.0317 (7)
H7A	0.3911	0.2741	0.7037	0.033 (8)*
C8	0.3495 (2)	0.1902 (2)	0.4032 (3)	0.0346 (7)
H8A	0.3371	0.1704	0.3231	0.054 (11)*
C9	0.3785 (2)	0.9917 (2)	0.4676 (3)	0.0301 (7)

	U11	U22	U33	U12	U13	U23
Cu1	0.0528 (3)	0.0168 (2)	0.0349 (2)	−0.00049 (16)	0.0233 (2)	−0.00040 (15)
Cl1	0.0435 (4)	0.0304 (4)	0.0372 (4)	0.0055 (3)	0.0290 (4)	0.0058 (3)
N1	0.069 (2)	0.0269 (14)	0.0416 (16)	0.0058 (13)	0.0335 (16)	−0.0005 (12)
N2	0.0465 (15)	0.0205 (12)	0.0401 (15)	−0.0013 (11)	0.0259 (13)	0.0008 (11)
N3	0.067 (2)	0.0263 (14)	0.0390 (16)	0.0078 (13)	0.0332 (16)	0.0024 (12)
N4	0.0431 (16)	0.0165 (12)	0.0435 (16)	0.0016 (10)	0.0265 (14)	−0.0001 (11)
N5	0.0371 (14)	0.0179 (12)	0.0321 (13)	−0.0020 (10)	0.0191 (12)	−0.0013 (10)
C1	0.0421 (19)	0.0278 (16)	0.0394 (18)	0.0039 (14)	0.0215 (16)	0.0070 (14)
C2	0.052 (2)	0.0180 (14)	0.0432 (19)	0.0075 (13)	0.0337 (18)	0.0074 (13)
C3	0.043 (2)	0.0164 (14)	0.051 (2)	0.0045 (13)	0.0234 (18)	0.0053 (14)
C4	0.0293 (15)	0.0182 (14)	0.0291 (15)	−0.0021 (11)	0.0153 (13)	−0.0002 (11)
C5	0.0465 (19)	0.0197 (14)	0.0325 (18)	−0.0001 (13)	0.0218 (16)	0.0043 (12)
C6	0.0415 (18)	0.0191 (14)	0.0348 (17)	−0.0026 (12)	0.0229 (15)	0.0023 (13)
C7	0.0423 (18)	0.0228 (15)	0.0328 (17)	−0.0037 (12)	0.0245 (16)	−0.0014 (12)
C8	0.0468 (19)	0.0257 (15)	0.0319 (17)	−0.0024 (13)	0.0246 (15)	−0.0009 (13)
C9	0.0357 (16)	0.0170 (14)	0.0347 (16)	−0.0027 (12)	0.0202 (14)	−0.0002 (12)

Cu1—N5	2.006 (2)	C1—H1C	0.9600
Cu1—C1	2.047 (3)	C2—C3	1.497 (4)
Cu1—C2	2.079 (3)	C2—H2A	0.9599
Cu1—Cl1i	2.3491 (11)	C3—H3A	0.9598
Cu1—Cl1	2.5358 (12)	C3—H3B	0.9599
Cl1—Cu1i	2.3491 (11)	C4—C8	1.384 (4)
N1—N4	1.310 (4)	C4—C6	1.381 (4)
N1—N3	1.319 (4)	C4—C9ii	1.471 (4)
N2—C9	1.325 (4)	C5—C8	1.378 (4)
N2—N4	1.330 (3)	C5—H5A	0.9600
N3—C9	1.341 (4)	C6—C7	1.379 (4)
N4—C3	1.464 (3)	C6—H6A	0.9599
N5—C5	1.336 (4)	C7—H7A	0.9600
N5—C7	1.345 (4)	C8—H8A	0.9600
C1—C2	1.351 (4)	C9—C4iii	1.471 (4)
C1—H1A	0.9600
N5—Cu1—C1	106.18 (11)	C3—C2—Cu1	109.4 (2)
N5—Cu1—C2	144.35 (12)	C1—C2—H2A	119.7
C1—Cu1—C2	38.23 (12)	C3—C2—H2A	119.1
N5—Cu1—Cl1i	104.01 (8)	Cu1—C2—H2A	91.1
C1—Cu1—Cl1i	130.46 (11)	N4—C3—C2	111.3 (3)
C2—Cu1—Cl1i	104.77 (10)	N4—C3—H3A	108.8
N5—Cu1—Cl1	97.23 (8)	C2—C3—H3A	108.7
C1—Cu1—Cl1	120.78 (11)	N4—C3—H3B	109.4
C2—Cu1—Cl1	101.90 (10)	C2—C3—H3B	110.4
Cl1i—Cu1—Cl1	92.81 (5)	H3A—C3—H3B	108.2
Cu1i—Cl1—Cu1	87.19 (5)	C8—C4—C6	118.1 (3)
N4—N1—N3	106.1 (3)	C8—C4—C9ii	120.6 (3)
C9—N2—N4	101.8 (2)	C6—C4—C9ii	121.2 (3)
N1—N3—C9	106.4 (3)	N5—C5—C8	123.4 (3)
N1—N4—N2	113.7 (2)	N5—C5—H5A	118.0
N1—N4—C3	122.7 (3)	C8—C5—H5A	118.6
N2—N4—C3	123.6 (3)	C7—C6—C4	119.5 (3)
C5—N5—C7	117.3 (2)	C7—C6—H6A	120.5
C5—N5—Cu1	120.90 (19)	C4—C6—H6A	119.9
C7—N5—Cu1	120.8 (2)	N5—C7—C6	122.6 (3)
C2—C1—Cu1	72.17 (18)	N5—C7—H7A	118.4
C2—C1—H1A	120.4	C6—C7—H7A	119.0
Cu1—C1—H1A	90.3	C4—C8—C5	119.0 (3)
C2—C1—H1C	119.6	C4—C8—H8A	120.2
Cu1—C1—H1C	107.9	C5—C8—H8A	120.8
H1A—C1—H1C	120.0	N2—C9—N3	112.0 (3)
C1—C2—C3	121.1 (3)	N2—C9—C4iii	123.9 (3)
C1—C2—Cu1	69.60 (17)	N3—C9—C4iii	124.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1i	0.96	2.81	3.459 (3)	126.