Bis(acetato-κ(2)O,O')(4,4'-dimethyl-2,2'-bipyridine-κ(2)N,N')-zinc.

The mol-ecular structure of the title compound, [Zn(CH(3)COO)(2)(C(12)H(12)N(2))], consists of isolated mol-ecules bis-ected by a twofold rotation axis which goes through the Zn(II) cation and halves the organic base through the central C-C bond. The Zn(II) ion is coordinated by two N atoms from one mol-ecule of the aromatic base and four O atoms from two bidentate, symmetry-related acetate anions, which coordinate asym-metrically [Zn-O distances of 2.058 (2) and 2.362 (3) Å], while the two Zn-N bond distances are equal as imposed by symmetry [2.079 (2) Å]. The crystal structure is supported by a number of weak C-H⋯O inter-actions and C-H⋯π contacts, with no π-π inter-actions present, mainly hindered by the substituent methyl groups and the relative mol-ecular orientation. The result is a three-dimensional structure in which each mol-ecule is linked to eight different neighbors.

Related literature

For properties of polypyridyl compounds, see: Steed & Atwood (2009 ▶). For related structures, see: Barquín et al. (2010 ▶). For details of the vectorial bond–valence model, see Harvey et al. (2006 ▶).

Experimental

Crystal data

[Zn(C2H3O2)2(n class="CellLine">C12H12N2)]

M = 367.71

Orthorhombic,

a = 14.4779 (5) Å

b = 28.5700 (15) Å

c = 8.0854 (3) Å

V = 3344.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.49 mm−1

T = 295 K

0.3 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.65, T max = 0.75

3945 measured reflections

1563 independent reflections

1481 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.09

1563 reflections

107 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 374 Friedel pairs

Flack parameter: 0.010 (16)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97 and PLATON (Spek, 2009) ▶.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042699/br2212sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042699/br2212Isup2.hkl

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

[Zn(C2H3O2)2(C12H12N2)]	F(000) = 1520
Mr = 367.71	Dx = 1.461 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1985 reflections
a = 14.4779 (5) Å	θ = 3.6–28.9°
b = 28.5700 (15) Å	µ = 1.49 mm−1
c = 8.0854 (3) Å	T = 295 K
V = 3344.4 (2) Å3	Prism, white
Z = 8	0.3 × 0.3 × 0.2 mm

Oxford Diffraction Gemini CCD S Ultra diffractometer	1481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans, thick slices	θmax = 29.0°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −17→18
Tmin = 0.65, Tmax = 0.75	k = −37→17
3945 measured reflections	l = −10→5
1563 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0402P)2 + 1.025P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1563 reflections	Δρmax = 0.28 e Å−3
107 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 374 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (16)

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	0	0.08552 (5)	0.04845 (13)
O1	−0.10026 (14)	0.03972 (8)	−0.0279 (3)	0.0745 (6)
N1	0.02563 (14)	0.04418 (7)	0.2846 (2)	0.0456 (4)
O2	−0.12535 (18)	−0.03328 (9)	−0.0599 (3)	0.0843 (7)
C4	0.01794 (12)	0.05180 (7)	0.5779 (5)	0.0421 (5)
H4	0.0071	0.038	0.6803	0.051*
C7	−0.14861 (19)	0.00731 (10)	−0.0837 (4)	0.0548 (7)
C5	0.01168 (12)	0.02544 (8)	0.4354 (3)	0.0361 (4)
C8	−0.2331 (2)	0.01806 (14)	−0.1800 (9)	0.0900 (14)
H8B	−0.2777	0.0328	−0.1093	0.135*
H8C	−0.2584	−0.0104	−0.2238	0.135*
H8A	−0.2178	0.0388	−0.2694	0.135*
C3	0.04052 (15)	0.09917 (8)	0.5683 (4)	0.0502 (5)
C1	0.0483 (2)	0.08971 (10)	0.2769 (4)	0.0604 (7)
H1	0.0586	0.103	0.1735	0.073*
C2	0.05697 (19)	0.11722 (9)	0.4128 (4)	0.0607 (7)
H2	0.0741	0.1484	0.401	0.073*
C6	0.0449 (2)	0.12828 (10)	0.7225 (4)	0.0719 (9)
H6A	0.0721	0.1103	0.8101	0.108*
H6C	−0.0164	0.1376	0.7538	0.108*
H6B	0.0818	0.1556	0.7024	0.108*

	U11	U22	U33	U12	U13	U23
Zn1	0.04289 (17)	0.0737 (3)	0.02871 (17)	0.01368 (17)	0	0
O1	0.0622 (11)	0.0907 (14)	0.0706 (15)	−0.0028 (10)	−0.0158 (11)	−0.0093 (12)
N1	0.0478 (10)	0.0549 (11)	0.0342 (11)	0.0047 (8)	0.0032 (8)	0.0080 (8)
O2	0.0909 (16)	0.0871 (15)	0.0749 (17)	0.0313 (12)	−0.0146 (13)	−0.0022 (13)
C4	0.0424 (11)	0.0480 (10)	0.0361 (11)	0.0034 (8)	−0.0042 (16)	0.0013 (12)
C7	0.0399 (12)	0.0850 (19)	0.0393 (14)	0.0085 (11)	0.0013 (10)	−0.0056 (13)
C5	0.0329 (9)	0.0459 (12)	0.0296 (11)	0.0036 (7)	−0.0017 (8)	0.0031 (9)
C8	0.061 (2)	0.109 (3)	0.100 (4)	0.0012 (17)	−0.037 (3)	0.017 (3)
C3	0.0452 (10)	0.0462 (11)	0.0593 (16)	0.0006 (9)	−0.0095 (12)	−0.0025 (12)
C1	0.0654 (15)	0.0602 (15)	0.0557 (18)	−0.0014 (12)	0.0060 (12)	0.0240 (13)
C2	0.0621 (16)	0.0440 (12)	0.076 (2)	−0.0032 (11)	−0.0005 (14)	0.0087 (14)
C6	0.080 (2)	0.0559 (15)	0.079 (2)	−0.0007 (14)	−0.0190 (17)	−0.0158 (16)

Zn1—O1i	2.058 (2)	C4—H4	0.93
Zn1—O1	2.058 (2)	C7—C8	1.482 (5)
Zn1—N1	2.079 (2)	C5—C5i	1.493 (4)
Zn1—N1i	2.079 (2)	C8—H8B	0.96
Zn1—O2	2.362 (3)	C8—H8C	0.96
Zn1—O2i	2.362 (3)	C8—H8A	0.96
Zn1—C7	2.558 (3)	C3—C2	1.380 (4)
Zn1—C7i	2.558 (3)	C3—C6	1.500 (4)
O1—C7	1.246 (3)	C1—C2	1.357 (4)
N1—C1	1.343 (3)	C1—H1	0.93
N1—C5	1.347 (3)	C2—H2	0.93
O2—C7	1.223 (3)	C6—H6A	0.96
C4—C5	1.380 (4)	C6—H6C	0.96
C4—C3	1.394 (3)	C6—H6B	0.96
O1i—Zn1—O1	127.09 (15)	C5—C4—C3	119.9 (3)
O1i—Zn1—N1	123.63 (9)	C5—C4—H4	120
O1—Zn1—N1	97.82 (8)	C3—C4—H4	120
O1i—Zn1—N1i	97.82 (8)	O2—C7—O1	119.6 (3)
O1—Zn1—N1i	123.63 (9)	O2—C7—C8	120.4 (3)
N1—Zn1—N1i	78.52 (11)	O1—C7—C8	120.0 (3)
O1i—Zn1—O2	95.63 (10)	O2—C7—Zn1	66.85 (17)
O1—Zn1—O2	57.21 (9)	O1—C7—Zn1	52.72 (15)
N1—Zn1—O2	140.08 (8)	C8—C7—Zn1	172.7 (2)
N1i—Zn1—O2	90.22 (9)	N1—C5—C4	122.0 (2)
O1i—Zn1—O2i	57.21 (9)	N1—C5—C5i	114.92 (13)
O1—Zn1—O2i	95.63 (10)	C4—C5—C5i	123.13 (15)
N1—Zn1—O2i	90.22 (9)	C7—C8—H8B	109.5
N1i—Zn1—O2i	140.08 (8)	C7—C8—H8C	109.5
O2—Zn1—O2i	120.30 (15)	H8B—C8—H8C	109.5
O1i—Zn1—C7	113.57 (9)	C7—C8—H8A	109.5
O1—Zn1—C7	28.79 (8)	H8B—C8—H8A	109.5
N1—Zn1—C7	120.97 (8)	H8C—C8—H8A	109.5
N1i—Zn1—C7	108.27 (9)	C2—C3—C4	117.0 (3)
O2—Zn1—C7	28.42 (8)	C2—C3—C6	122.9 (2)
O2i—Zn1—C7	110.31 (10)	C4—C3—C6	120.1 (3)
O1i—Zn1—C7i	28.79 (8)	N1—C1—C2	123.1 (2)
O1—Zn1—C7i	113.57 (9)	N1—C1—H1	118.5
N1—Zn1—C7i	108.27 (9)	C2—C1—H1	118.5
N1i—Zn1—C7i	120.97 (8)	C1—C2—C3	120.4 (2)
O2—Zn1—C7i	110.31 (10)	C1—C2—H2	119.8
O2i—Zn1—C7i	28.42 (8)	C3—C2—H2	119.8
C7—Zn1—C7i	115.34 (13)	C3—C6—H6A	109.5
C7—O1—Zn1	98.50 (18)	C3—C6—H6C	109.5
C1—N1—C5	117.6 (2)	H6A—C6—H6C	109.5
C1—N1—Zn1	126.56 (18)	C3—C6—H6B	109.5
C5—N1—Zn1	115.64 (15)	H6A—C6—H6B	109.5
C7—O2—Zn1	84.73 (19)	H6C—C6—H6B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ii	0.93	2.53	3.354 (4)	147
C6—H6A···O2iii	0.96	2.56	3.438 (4)	153
C4—H4···Cg1iv	0.93	2.99	3.874 (4)	160
C4—H4···Cg1iii	0.93	2.96	3.766 (4)	145
C8—H8B···Cg2v	0.96	2.96	3.804 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the Zn1,O1,C7,O2 and N1,C1–C5 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.53	3.354 (4)	147
C6—H6A⋯O2ii	0.96	2.56	3.438 (4)	153
C4—H4⋯Cg1iii	0.93	2.99	3.874 (4)	160
C4—H4⋯Cg1ii	0.93	2.96	3.766 (4)	145
C8—H8B⋯Cg2iv	0.96	2.96	3.804 (4)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .