Dichlorido(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

In the title compound, [ZnCl(2)(C(12)H(12)N(2))], the complete mol-ecule is generated by crystallographic mirror symmetry, with the Zn atom and both chloride ions lying on the reflecting plane, yielding a distorted ZnN(2)Cl(2) tetra-hedral coordination for the metal ion. In the crystal, there are π-π contacts between the pyridine rings [centroid-centroid distance = 3.7857 (17) Å].

Related literature

For related structures containing Zn bonded to two n class="Chemical">chloride ions and a phenanthroline/bipyridine derivative, see: Ahmadi et al. (2008 ▶, 2009a ▶,b ▶); Alizadeh et al. (2009 ▶); Gruia et al. (2007 ▶); Khalighi et al. (2008 ▶); Khan & Tuck (1984 ▶); Khavasi et al. (2008 ▶); Khoshtarkib et al. (2009 ▶); Kozhevnikov et al. (2006 ▶); Liu et al. (2004 ▶); Preston & Kennard (1969 ▶); Reimann et al. (1966 ▶).

Experimental

Crystal data

[ZnCl2(n class="CellLine">C12H12N2)]

M = 320.53

Monoclinic,

a = 7.6957 (15) Å

b = 11.266 (2) Å

c = 8.1431 (16) Å

β = 110.61 (3)°

V = 660.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.24 mm−1

T = 298 K

0.40 × 0.33 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.421, T max = 0.512

8852 measured reflections

2075 independent reflections

1972 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.101

S = 1.26

2075 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038215/hb5106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038215/hb5106Isup2.hkl

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

[ZnCl2(C12H12N2)]	F(000) = 324
Mr = 320.53	Dx = 1.611 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1170 reflections
a = 7.6957 (15) Å	θ = 2.8–30.6°
b = 11.266 (2) Å	µ = 2.24 mm−1
c = 8.1431 (16) Å	T = 298 K
β = 110.61 (3)°	Prism, colourless
V = 660.8 (3) Å3	0.40 × 0.33 × 0.30 mm
Z = 2

Bruker SMART CCD diffractometer	2075 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 30.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→10
Tmin = 0.421, Tmax = 0.512	k = −16→16
8852 measured reflections	l = −11→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.26	w = 1/[σ2(Fo2) + (0.036P)2 + 0.4143P] where P = (Fo2 + 2Fc2)/3
2075 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.55 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
C1	0.9103 (5)	1.0397 (3)	0.7493 (4)	0.0605 (7)
H1A	0.8626	1.0161	0.8386	0.091*
H1B	0.9085	1.1247	0.7405	0.091*
H1C	1.0355	1.0117	0.7793	0.091*
C2	0.7921 (3)	0.9875 (2)	0.5768 (3)	0.0415 (5)
C3	0.6959 (4)	1.0566 (2)	0.4331 (4)	0.0525 (6)
H3	0.7041	1.1389	0.4413	0.063*
C4	0.5891 (4)	1.0046 (3)	0.2791 (4)	0.0524 (6)
H4	0.5246	1.0512	0.1825	0.063*
C5	0.5776 (3)	0.8820 (2)	0.2679 (3)	0.0424 (5)
H5	0.5053	0.8449	0.1644	0.051*
C6	0.6762 (3)	0.81599 (18)	0.4143 (3)	0.0317 (4)
N1	0.7813 (2)	0.86822 (16)	0.5661 (2)	0.0330 (3)
Cl1	1.20088 (11)	0.7500	0.88188 (13)	0.0521 (2)
Cl2	0.74082 (14)	0.7500	0.94980 (13)	0.0511 (2)
Zn1	0.89560 (5)	0.7500	0.76788 (4)	0.03392 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0688 (19)	0.0401 (13)	0.0625 (17)	−0.0094 (12)	0.0104 (15)	−0.0154 (12)
C2	0.0457 (12)	0.0306 (10)	0.0480 (12)	−0.0039 (8)	0.0162 (10)	−0.0032 (8)
C3	0.0694 (17)	0.0281 (10)	0.0616 (16)	0.0033 (10)	0.0249 (14)	0.0063 (10)
C4	0.0641 (16)	0.0434 (13)	0.0473 (13)	0.0122 (12)	0.0168 (12)	0.0161 (11)
C5	0.0453 (12)	0.0424 (12)	0.0342 (10)	0.0048 (9)	0.0074 (9)	0.0057 (9)
C6	0.0326 (9)	0.0308 (9)	0.0300 (8)	0.0014 (7)	0.0091 (7)	0.0016 (7)
N1	0.0341 (8)	0.0288 (8)	0.0328 (8)	−0.0010 (6)	0.0075 (6)	−0.0002 (6)
Cl1	0.0325 (4)	0.0642 (6)	0.0492 (5)	0.000	0.0014 (3)	0.000
Cl2	0.0548 (5)	0.0567 (5)	0.0479 (4)	0.000	0.0255 (4)	0.000
Zn1	0.03172 (18)	0.03621 (19)	0.02830 (18)	0.000	0.00368 (12)	0.000

C1—C2	1.499 (4)	C4—H4	0.9300
C1—H1A	0.9600	C5—C6	1.383 (3)
C1—H1B	0.9600	C5—H5	0.9300
C1—H1C	0.9600	C6—N1	1.350 (3)
C2—N1	1.347 (3)	C6—C6i	1.487 (4)
C2—C3	1.384 (4)	Zn1—N1	2.0569 (18)
C3—C4	1.366 (4)	Zn1—Cl1	2.2013 (11)
C3—H3	0.9300	Zn1—Cl2	2.2035 (10)
C4—C5	1.386 (4)	Zn1—N1i	2.0569 (18)
C2—C1—H1A	109.5	C6—C5—C4	118.4 (2)
C2—C1—H1B	109.5	C6—C5—H5	120.8
H1A—C1—H1B	109.5	C4—C5—H5	120.8
C2—C1—H1C	109.5	N1—C6—C5	121.6 (2)
H1A—C1—H1C	109.5	N1—C6—C6i	115.83 (11)
H1B—C1—H1C	109.5	C5—C6—C6i	122.51 (14)
N1—C2—C3	120.3 (2)	C2—N1—C6	119.82 (19)
N1—C2—C1	117.1 (2)	C2—N1—Zn1	126.50 (16)
C3—C2—C1	122.6 (2)	C6—N1—Zn1	113.51 (13)
C4—C3—C2	120.3 (2)	N1i—Zn1—N1	80.71 (10)
C4—C3—H3	119.8	N1i—Zn1—Cl1	115.45 (6)
C2—C3—H3	119.8	N1—Zn1—Cl1	115.45 (6)
C3—C4—C5	119.5 (2)	N1i—Zn1—Cl2	110.90 (6)
C3—C4—H4	120.3	N1—Zn1—Cl2	110.90 (6)
C5—C4—H4	120.3	Cl1—Zn1—Cl2	117.76 (5)
N1—C2—C3—C4	0.0 (4)	C5—C6—N1—C2	−0.2 (3)
C1—C2—C3—C4	−179.6 (3)	C6i—C6—N1—C2	178.78 (16)
C2—C3—C4—C5	0.1 (5)	C5—C6—N1—Zn1	175.34 (17)
C3—C4—C5—C6	−0.2 (4)	C6i—C6—N1—Zn1	−5.7 (3)
C4—C5—C6—N1	0.3 (4)	C2—N1—Zn1—N1i	−178.10 (16)
C4—C5—C6—C6i	−178.63 (19)	C6—N1—Zn1—N1i	6.69 (17)
C3—C2—N1—C6	0.0 (4)	C2—N1—Zn1—Cl1	−64.2 (2)
C1—C2—N1—C6	179.7 (2)	C6—N1—Zn1—Cl1	120.55 (13)
C3—C2—N1—Zn1	−174.88 (19)	C2—N1—Zn1—Cl2	73.0 (2)
C1—C2—N1—Zn1	4.7 (3)	C6—N1—Zn1—Cl2	−102.24 (14)

Zn1—N1	2.0569 (18)
Zn1—Cl1	2.2013 (11)
Zn1—Cl2	2.2035 (10)

N1i—Zn1—N1

80.71 (10)

Symmetry code: (i) .