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

The title compound, [CuCl(C(9)H(9)N(5))](n), prepared by solvo-thermal synthesis, is a new homometallic Cu(I)-olefin coordination polymer in which the Cu(I) atoms are linked by the 3-(2-allyl-2H-tetra-zol-5-yl)pyridine ligands and are each bonded to one terminal Cl atom. The organic ligand acts as a bidentate ligand bridging two neighboring Cu centers through the bonds to the N atom of the pyridine ring and the double bond of the allyl group. Weak Cu⋯Cl [3.136 (8) Å), C-H⋯Cl and C-H⋯N inter-actions connect the coordination polymers into a three-dimensional structure.

Related literature

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

Experimental

Crystal data

[CuCl(C9H9N5)]

M = 286.21

Triclinic,

a = 7.3005 (15) Å

b = 7.6560 (15) Å

c = 9.981 (2) Å

α = 80.51 (3)°

β = 77.00 (3)°

γ = 84.68 (3)°

V = 535.23 (19) Å3

Z = 2

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 = 0.806, T max = 1.000 (expected range = 0.643–0.797)

5572 measured reflections

2443 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.103

S = 1.16

2443 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.46 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 SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013895/gk2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013895/gk2142Isup2.hkl

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

[CuCl(C9H9N5)]	Z = 2
Mr = 286.21	F(000) = 288
Triclinic, P1	Dx = 1.776 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3005 (15) Å	Cell parameters from 5070 reflections
b = 7.6560 (15) Å	θ = 3.2–27.5°
c = 9.981 (2) Å	µ = 2.27 mm−1
α = 80.51 (3)°	T = 293 K
β = 77.00 (3)°	Block, colorless
γ = 84.68 (3)°	0.2 × 0.15 × 0.1 mm
V = 535.23 (19) Å3

Rigaku Mercury2 diffractometer	2443 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.806, Tmax = 1	l = −12→12
5572 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0388P)2] where P = (Fo2 + 2Fc2)/3
2443 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.46 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
Cu1	0.15988 (6)	−0.16243 (6)	0.38989 (4)	0.03499 (17)
Cl3	−0.15148 (11)	−0.11291 (11)	0.40805 (10)	0.0362 (2)
N1	0.2905 (4)	0.0083 (4)	0.2319 (3)	0.0273 (6)
N2	0.0888 (4)	0.4924 (4)	−0.2268 (3)	0.0288 (6)
N3	0.2403 (4)	0.4402 (4)	−0.1738 (3)	0.0307 (7)
N4	−0.0077 (4)	0.2863 (4)	−0.0651 (3)	0.0365 (7)
N5	−0.0620 (4)	0.4030 (4)	−0.1640 (3)	0.0363 (7)
C1	0.4677 (5)	0.0501 (5)	0.2253 (3)	0.0345 (8)
H1A	0.5306	−0.0055	0.2974	0.039 (10)*
C2	0.5620 (5)	0.1711 (5)	0.1194 (4)	0.0375 (9)
H2A	0.6894	0.1957	0.1169	0.034 (10)*
C3	0.4697 (5)	0.2565 (5)	0.0182 (4)	0.0344 (8)
H3A	0.5327	0.3399	−0.0568	0.040 (10)*
C4	0.2031 (5)	0.0904 (4)	0.1323 (3)	0.0266 (7)
H4A	0.0779	0.0591	0.1349	0.029 (9)*
C5	0.2858 (4)	0.2174 (4)	0.0256 (3)	0.0256 (7)
C6	0.0802 (5)	0.6439 (4)	−0.3365 (3)	0.0307 (8)
H6A	0.1222	0.7458	−0.3100	0.030 (10)*
H6B	−0.0483	0.6696	−0.3450	0.037 (10)*
C7	0.1745 (5)	0.3120 (4)	−0.0734 (3)	0.0266 (7)
C8	0.1990 (5)	0.6128 (4)	−0.4751 (3)	0.0303 (8)
H8A	0.1838	0.5028	−0.5045	0.028 (9)*
C9	0.3666 (5)	0.6878 (5)	−0.5325 (4)	0.0414 (10)
H9A	0.4217	0.7393	−0.4705	0.075 (16)*
H9B	0.4567	0.6248	−0.5960	0.066 (14)*

	U11	U22	U33	U12	U13	U23
Cu1	0.0274 (3)	0.0380 (3)	0.0312 (3)	−0.00009 (18)	−0.00526 (18)	0.01645 (19)
Cl3	0.0272 (5)	0.0346 (5)	0.0449 (5)	−0.0015 (3)	−0.0117 (4)	0.0051 (4)
N1	0.0277 (15)	0.0261 (14)	0.0234 (13)	−0.0003 (11)	−0.0041 (12)	0.0069 (11)
N2	0.0307 (15)	0.0278 (15)	0.0243 (14)	−0.0005 (12)	−0.0062 (12)	0.0058 (12)
N3	0.0346 (16)	0.0295 (15)	0.0253 (14)	−0.0053 (12)	−0.0076 (13)	0.0070 (12)
N4	0.0345 (17)	0.0377 (17)	0.0304 (16)	−0.0084 (13)	−0.0051 (13)	0.0160 (14)
N5	0.0321 (17)	0.0388 (18)	0.0335 (16)	−0.0084 (13)	−0.0049 (13)	0.0086 (14)
C1	0.0304 (19)	0.045 (2)	0.0252 (17)	−0.0044 (16)	−0.0086 (15)	0.0090 (16)
C2	0.0280 (19)	0.042 (2)	0.043 (2)	−0.0100 (16)	−0.0110 (16)	0.0004 (18)
C3	0.037 (2)	0.033 (2)	0.0295 (18)	−0.0104 (16)	−0.0036 (16)	0.0069 (16)
C4	0.0246 (17)	0.0270 (17)	0.0235 (16)	−0.0051 (13)	−0.0012 (13)	0.0061 (13)
C5	0.0284 (17)	0.0243 (16)	0.0221 (15)	−0.0020 (13)	−0.0028 (14)	−0.0010 (13)
C6	0.037 (2)	0.0258 (18)	0.0246 (17)	0.0003 (15)	−0.0068 (15)	0.0069 (14)
C7	0.0304 (18)	0.0234 (17)	0.0223 (16)	−0.0028 (14)	−0.0014 (14)	0.0024 (13)
C8	0.036 (2)	0.0221 (17)	0.0275 (17)	0.0038 (14)	−0.0066 (15)	0.0073 (14)
C9	0.0293 (19)	0.041 (2)	0.046 (2)	0.0094 (16)	−0.0110 (18)	0.0140 (18)

Cu1—N1	1.995 (3)	C2—H2A	0.9600
Cu1—C9i	2.026 (3)	C3—C5	1.386 (5)
Cu1—C8i	2.044 (3)	C3—H3A	0.9600
Cu1—Cl3	2.2408 (10)	C4—C5	1.387 (4)
N1—C4	1.340 (4)	C4—H4A	0.9601
N1—C1	1.345 (4)	C5—C7	1.476 (4)
N2—N5	1.327 (4)	C6—C8	1.501 (5)
N2—N3	1.332 (4)	C6—H6A	0.9600
N2—C6	1.465 (4)	C6—H6B	0.9600
N3—C7	1.321 (4)	C8—C9	1.364 (5)
N4—N5	1.323 (4)	C8—Cu1ii	2.044 (3)
N4—C7	1.344 (4)	C8—H8A	0.9600
C1—C2	1.384 (5)	C9—Cu1ii	2.026 (3)
C1—H1A	0.9599	C9—H9A	0.9600
C2—C3	1.382 (5)	C9—H9B	0.9600
N1—Cu1—C9i	105.86 (13)	C5—C4—H4A	118.6
N1—Cu1—C8i	143.90 (13)	C3—C5—C4	118.7 (3)
C9i—Cu1—C8i	39.16 (14)	C3—C5—C7	121.7 (3)
N1—Cu1—Cl3	108.44 (9)	C4—C5—C7	119.6 (3)
C9i—Cu1—Cl3	145.70 (11)	N2—C6—C8	113.1 (3)
C8i—Cu1—Cl3	106.88 (10)	N2—C6—H6A	108.9
C4—N1—C1	117.8 (3)	C8—C6—H6A	108.7
C4—N1—Cu1	121.4 (2)	N2—C6—H6B	109.0
C1—N1—Cu1	120.7 (2)	C8—C6—H6B	109.1
N5—N2—N3	113.9 (3)	H6A—C6—H6B	107.9
N5—N2—C6	121.6 (3)	N3—C7—N4	112.9 (3)
N3—N2—C6	124.2 (3)	N3—C7—C5	123.1 (3)
C7—N3—N2	101.4 (3)	N4—C7—C5	123.8 (3)
N5—N4—C7	106.3 (3)	C9—C8—C6	123.7 (4)
N4—N5—N2	105.5 (3)	C9—C8—Cu1ii	69.73 (19)
N1—C1—C2	122.6 (3)	C6—C8—Cu1ii	105.9 (2)
N1—C1—H1A	118.6	C9—C8—H8A	115.7
C2—C1—H1A	118.8	C6—C8—H8A	115.7
C3—C2—C1	119.0 (3)	Cu1ii—C8—H8A	116.0
C3—C2—H2A	120.6	C8—C9—Cu1ii	71.11 (19)
C1—C2—H2A	120.4	C8—C9—H9A	115.8
C2—C3—C5	118.8 (3)	Cu1ii—C9—H9A	116.3
C2—C3—H3A	120.5	C8—C9—H9B	117.2
C5—C3—H3A	120.7	Cu1ii—C9—H9B	116.7
N1—C4—C5	123.0 (3)	H9A—C9—H9B	113.5
N1—C4—H4A	118.4

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl3iii	0.96	2.79	3.675 (4)	154.
C2—H2A···N4iii	0.96	2.59	3.379 (5)	139.
C4—H4A···N4	0.96	2.57	2.909 (4)	101.
C6—H6A···Cl3iv	0.96	2.83	3.607 (4)	139.

Cu1—N1	1.995 (3)
Cu1—C9i	2.026 (3)
Cu1—C8i	2.044 (3)
Cu1—Cl3	2.2408 (10)

N1—Cu1—C9i	105.86 (13)
N1—Cu1—C8i	143.90 (13)
C9i—Cu1—C8i	39.16 (14)
N1—Cu1—Cl3	108.44 (9)
C9i—Cu1—Cl3	145.70 (11)
C8i—Cu1—Cl3	106.88 (10)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl3ii	0.96	2.79	3.675 (4)	154
C2—H2A⋯N4ii	0.96	2.59	3.379 (5)	139
C4—H4A⋯N4	0.96	2.57	2.909 (4)	101
C6—H6A⋯Cl3iii	0.96	2.83	3.607 (4)	139

Symmetry codes: (ii) ; (iii) .