Dichloridobis(2-phenyl-pyridine-κN)zinc(II).

In the title compound, [ZnCl(2)(C(11)H(9)N)(2)], the Zn(2+) cation lies on a twofold axis and is coordinated by two Cl(-) anions and the N atoms of two 2-phenyl-pyridine ligands, forming a ZnN(2)Cl(2) polyhedron with a slightly distorted tetra-hedral coordination geometry. The dihedral angle between the phenyl ring and the metal-bound pyridine ring is 50.3 (4)° for each 2-phenyl-pyridine ligand. This arranges the phenyl ring from one ligand in the complex above the pyridine ring of the other resulting in an intra-molecular π-π inter-action, with a centroid-centroid distance of 3.6796 (17) Å. Weak C-H⋯Cl hydrogen bonds stabilize the crystal packing, linking mol-ecules into chains along the c axis.

Related literature

For background to metal complexes with 2-phenyl­pyridine ligands, see: Samha et al. (1993 ▶); Yoshinari et al. (2010 ▶); Zhao et al. (2008 ▶). For those involving substituted 2-phenyl­pyridine ligands, see: Santoro et al. (2011 ▶).

Experimental

Crystal data

[ZnCl2(C11H9N)2]

M = 446.67

Tetragonal,

a = 15.2803 (3) Å

c = 16.4339 (7) Å

V = 3837.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.57 mm−1

T = 200 K

0.31 × 0.29 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.814, T max = 1.00

13165 measured reflections

2231 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.074

S = 1.09

2231 reflections

123 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 997 Friedel pairs

Flack parameter: 0.02 (2)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010616/sj5207sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010616/sj5207Isup2.hkl

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

[ZnCl2(C11H9N)2]	Dx = 1.546 Mg m−3
Mr = 446.67	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41cd	Cell parameters from 4803 reflections
Hall symbol: I 4bw -2c	θ = 2.7–28.1°
a = 15.2803 (3) Å	µ = 1.57 mm−1
c = 16.4339 (7) Å	T = 200 K
V = 3837.1 (2) Å3	Block, colorless
Z = 8	0.31 × 0.29 × 0.14 mm
F(000) = 1824

Bruker SMART CCD area-detector diffractometer	2231 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→20
Tmin = 0.814, Tmax = 1.00	k = −20→20
13165 measured reflections	l = −21→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0275P)2 + 1.0418P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2231 reflections	Δρmax = 0.37 e Å−3
123 parameters	Δρmin = −0.36 e Å−3
1 restraint	Absolute structure: Flack (1983), 997 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (2)

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
Zn1	0.0000	0.0000	0.48912 (7)	0.02540 (12)
N1	0.08480 (15)	−0.05713 (15)	0.40397 (14)	0.0207 (5)
C1	0.08984 (19)	−0.14499 (19)	0.40824 (18)	0.0265 (6)
H1	0.0670	−0.1733	0.4551	0.032*
C2	0.12652 (19)	−0.19583 (19)	0.34786 (19)	0.0298 (7)
H2	0.1299	−0.2576	0.3536	0.036*
C3	0.1581 (2)	−0.1554 (2)	0.27923 (19)	0.0329 (7)
H3	0.1834	−0.1888	0.2365	0.039*
C4	0.1525 (2)	−0.0650 (2)	0.27340 (18)	0.0291 (7)
H4	0.1735	−0.0361	0.2261	0.035*
C5	0.11645 (16)	−0.01706 (17)	0.33602 (17)	0.0222 (6)
C6	0.11275 (18)	0.07988 (17)	0.33127 (17)	0.0226 (6)
C7	0.1446 (2)	0.13120 (19)	0.39417 (19)	0.0298 (7)
H7	0.1688	0.1040	0.4411	0.036*
C8	0.1416 (2)	0.2216 (2)	0.3894 (2)	0.0373 (8)
H8	0.1634	0.2564	0.4328	0.045*
C9	0.1067 (2)	0.2607 (2)	0.3209 (2)	0.0389 (8)
H9	0.1040	0.3227	0.3174	0.047*
C10	0.0756 (2)	0.2102 (2)	0.2572 (2)	0.0353 (8)
H10	0.0520	0.2376	0.2102	0.042*
C11	0.0787 (2)	0.1198 (2)	0.26203 (17)	0.0285 (7)
H11	0.0577	0.0851	0.2182	0.034*
Cl1	0.04582 (6)	0.10755 (6)	0.57169 (5)	0.0421 (2)

	U11	U22	U33	U12	U13	U23
Zn1	0.0278 (3)	0.0310 (3)	0.0174 (2)	0.0033 (2)	0.000	0.000
N1	0.0218 (12)	0.0206 (12)	0.0196 (12)	0.0022 (10)	−0.0029 (10)	0.0004 (10)
C1	0.0260 (17)	0.0283 (16)	0.0253 (15)	0.0001 (13)	−0.0036 (13)	0.0026 (13)
C2	0.0321 (17)	0.0206 (15)	0.0368 (18)	0.0012 (12)	−0.0012 (13)	−0.0022 (13)
C3	0.0350 (18)	0.0287 (18)	0.0350 (18)	0.0024 (14)	0.0066 (15)	−0.0096 (15)
C4	0.0316 (17)	0.0297 (17)	0.0260 (15)	−0.0030 (13)	0.0089 (13)	0.0005 (13)
C5	0.0164 (13)	0.0272 (15)	0.0229 (16)	−0.0006 (11)	−0.0030 (11)	0.0014 (12)
C6	0.0216 (14)	0.0202 (13)	0.0262 (16)	0.0004 (12)	0.0049 (12)	0.0025 (12)
C7	0.0288 (17)	0.0308 (17)	0.0297 (17)	0.0000 (13)	−0.0015 (13)	0.0027 (13)
C8	0.0353 (19)	0.0274 (17)	0.049 (2)	−0.0038 (15)	0.0000 (16)	−0.0047 (15)
C9	0.0400 (18)	0.0252 (15)	0.051 (2)	0.0026 (15)	0.0091 (17)	0.0056 (17)
C10	0.0346 (17)	0.0371 (18)	0.0344 (19)	0.0056 (14)	0.0054 (14)	0.0184 (14)
C11	0.0266 (16)	0.0325 (17)	0.0264 (18)	0.0005 (13)	0.0038 (12)	0.0050 (13)
Cl1	0.0487 (5)	0.0513 (5)	0.0262 (4)	−0.0041 (4)	−0.0028 (4)	−0.0125 (4)

Zn1—N1	2.097 (2)	C4—H4	0.9500
Zn1—N1i	2.097 (2)	C5—C6	1.484 (4)
Zn1—Cl1i	2.2432 (11)	C6—C7	1.386 (4)
Zn1—Cl1	2.2432 (11)	C6—C11	1.392 (4)
N1—C1	1.347 (4)	C7—C8	1.384 (4)
N1—C5	1.362 (3)	C7—H7	0.9500
C1—C2	1.379 (4)	C8—C9	1.382 (5)
C1—H1	0.9500	C8—H8	0.9500
C2—C3	1.374 (4)	C9—C10	1.384 (5)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.388 (4)	C10—C11	1.384 (4)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.378 (4)	C11—H11	0.9500
N1—Zn1—N1i	96.30 (13)	N1—C5—C4	121.0 (2)
N1—Zn1—Cl1i	106.95 (7)	N1—C5—C6	118.6 (2)
N1i—Zn1—Cl1i	121.04 (6)	C4—C5—C6	120.4 (2)
N1—Zn1—Cl1	121.04 (6)	C7—C6—C11	119.6 (3)
N1i—Zn1—Cl1	106.95 (7)	C7—C6—C5	120.8 (2)
Cl1i—Zn1—Cl1	105.55 (7)	C11—C6—C5	119.6 (3)
C1—N1—C5	118.1 (2)	C8—C7—C6	120.7 (3)
C1—N1—Zn1	114.56 (19)	C8—C7—H7	119.6
C5—N1—Zn1	125.39 (18)	C6—C7—H7	119.6
N1—C1—C2	123.2 (3)	C9—C8—C7	119.3 (3)
N1—C1—H1	118.4	C9—C8—H8	120.3
C2—C1—H1	118.4	C7—C8—H8	120.3
C3—C2—C1	118.7 (3)	C8—C9—C10	120.5 (3)
C3—C2—H2	120.6	C8—C9—H9	119.7
C1—C2—H2	120.6	C10—C9—H9	119.7
C2—C3—C4	118.8 (3)	C9—C10—C11	120.1 (3)
C2—C3—H3	120.6	C9—C10—H10	120.0
C4—C3—H3	120.6	C11—C10—H10	120.0
C5—C4—C3	120.2 (3)	C10—C11—C6	119.8 (3)
C5—C4—H4	119.9	C10—C11—H11	120.1
C3—C4—H4	119.9	C6—C11—H11	120.1

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ii	0.95	2.90	3.666 (3)	138

Table 1

Selected bond lengths (Å)

Zn1—N1	2.097 (2)
Zn1—Cl1	2.2432 (11)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1i	0.95	2.90	3.666 (3)	138

Symmetry code: (i) .