(2,2'-Bipyridine-κN,N')bis-(4-chloro-benzoato-κO)zinc.

In the title compound, [Zn(C(7)H(4)ClO(2))(2)(C(10)H(8)N(2))], the Zn(II) atom is coordinated by two O atoms from two 4-chloro-benzoate ligands and two N atoms from a chelating 2,2'-bipyridine (bpy) mol-ecule in a distorted N(2)O(2) tetra-hedral geometry. The Zn(II) atom is located on a twofold rotation axis, which also passes through the mid-point of the central C-C bond of the bpy ligand. In the crystal, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions between the pyridine rings of the bpy ligands [centroid-centroid distance = 3.642 (3) Å] link the complex mol-ecules into a two-dimensional supra-molecular structure parallel to (100). An intra-molecular C-H⋯O hydrogen bond is also observed.

Related literature

For zinc(II) complexes with substituted n class="Chemical">benzoate ligands, see: Aghabozorg et al. (2005 ▶); Chen et al. (2006 ▶); Hökelek et al. (2008 ▶); Lemoine et al. (2004 ▶); Liu et al. (1998 ▶); Wei et al. (2002 ▶, 2004 ▶); Xu et al. (2004 ▶); Ye & Zhang (2010 ▶); Zhang et al. (2009 ▶, 2010 ▶); Zhou et al. (2005 ▶).

Experimental

Crystal data

[Zn(C7H4ClO2)2(C10n class="Species">H8N2)]

M = 532.68

Monoclinic,

a = 11.453 (2) Å

b = 8.4896 (17) Å

c = 12.337 (3) Å

β = 107.12 (3)°

V = 1146.4 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.34 mm−1

T = 290 K

0.32 × 0.25 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.675, T max = 0.787

8641 measured reflections

2012 independent reflections

1560 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.17

2012 reflections

150 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.36 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200699X/hy2516sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200699X/hy2516Isup2.hkl

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

[Zn(C7H4ClO2)2(C10H8N2)]	F(000) = 540
Mr = 532.68	Dx = 1.543 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 6683 reflections
a = 11.453 (2) Å	θ = 3.0–25.0°
b = 8.4896 (17) Å	µ = 1.34 mm−1
c = 12.337 (3) Å	T = 290 K
β = 107.12 (3)°	Block, colorless
V = 1146.4 (5) Å3	0.32 × 0.25 × 0.18 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2012 independent reflections
Radiation source: rotation anode	1560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.675, Tmax = 0.787	k = −9→10
8641 measured reflections	l = −14→14

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) = 0.121	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.051P)2 + 0.432P] where P = (Fo2 + 2Fc2)/3
2012 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.53 e Å−3
48 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.78102 (6)	0.2500	0.0564 (2)
Cl2	0.59680 (10)	1.35611 (14)	0.61254 (11)	0.0912 (4)
O1	0.1788 (3)	0.9459 (3)	0.2186 (2)	0.0738 (7)
O2	0.1206 (2)	0.8948 (3)	0.3696 (2)	0.0650 (7)
C1	−0.1402 (4)	0.6021 (6)	0.3867 (4)	0.0889 (13)
H1	−0.1636	0.7013	0.4048	0.107*
C2	−0.1780 (5)	0.4710 (8)	0.4330 (5)	0.122 (2)
H2	−0.2269	0.4814	0.4808	0.146*
C3	−0.1427 (7)	0.3267 (9)	0.4076 (6)	0.144 (3)
H3	−0.1657	0.2369	0.4394	0.172*
C4	−0.0731 (6)	0.3138 (6)	0.3351 (5)	0.121 (2)
H4	−0.0493	0.2150	0.3168	0.145*
C5	−0.0377 (4)	0.4489 (4)	0.2888 (3)	0.0827 (13)
N1	−0.0713 (3)	0.5916 (3)	0.3171 (3)	0.0686 (8)
C6	0.2915 (3)	1.0622 (4)	0.3941 (3)	0.0512 (8)
C7	0.3756 (4)	1.1328 (5)	0.3489 (3)	0.0679 (10)
H7	0.3691	1.1184	0.2726	0.082*
C8	0.4688 (4)	1.2242 (5)	0.4152 (4)	0.0741 (11)
H8	0.5246	1.2720	0.3842	0.089*
C9	0.4779 (3)	1.2436 (4)	0.5275 (4)	0.0629 (10)
C10	0.3952 (4)	1.1763 (5)	0.5739 (3)	0.0690 (10)
H10	0.4017	1.1915	0.6501	0.083*
C11	0.3019 (3)	1.0853 (4)	0.5063 (3)	0.0614 (9)
H11	0.2455	1.0391	0.5375	0.074*
C12	0.1909 (3)	0.9613 (4)	0.3207 (3)	0.0553 (8)

	U11	U22	U33	U12	U13	U23
Zn1	0.0659 (4)	0.0427 (3)	0.0618 (4)	0.000	0.0206 (3)	0.000
Cl2	0.0755 (7)	0.0805 (7)	0.1037 (9)	−0.0151 (6)	0.0048 (6)	−0.0030 (6)
O1	0.097 (2)	0.0728 (16)	0.0544 (16)	−0.0092 (15)	0.0258 (14)	−0.0083 (13)
O2	0.0722 (16)	0.0637 (15)	0.0639 (16)	−0.0123 (13)	0.0275 (13)	−0.0042 (12)
C1	0.080 (3)	0.105 (3)	0.081 (3)	−0.019 (2)	0.021 (2)	0.025 (2)
C2	0.104 (4)	0.151 (4)	0.097 (4)	−0.054 (4)	0.009 (3)	0.050 (4)
C3	0.165 (6)	0.116 (4)	0.110 (5)	−0.073 (4)	−0.021 (4)	0.058 (4)
C4	0.161 (5)	0.059 (3)	0.103 (4)	−0.040 (3)	−0.023 (3)	0.024 (3)
C5	0.104 (3)	0.0480 (18)	0.069 (3)	−0.013 (2)	−0.018 (2)	0.0074 (17)
N1	0.073 (2)	0.0545 (17)	0.070 (2)	−0.0075 (15)	0.0080 (16)	0.0108 (14)
C6	0.0590 (19)	0.0428 (16)	0.055 (2)	0.0036 (15)	0.0216 (15)	0.0031 (14)
C7	0.077 (3)	0.072 (2)	0.064 (2)	−0.006 (2)	0.035 (2)	−0.0049 (19)
C8	0.070 (3)	0.075 (3)	0.086 (3)	−0.012 (2)	0.038 (2)	0.002 (2)
C9	0.061 (2)	0.0511 (19)	0.074 (3)	0.0037 (17)	0.0154 (19)	0.0019 (17)
C10	0.079 (3)	0.072 (2)	0.054 (2)	−0.007 (2)	0.0172 (19)	−0.0008 (18)
C11	0.068 (2)	0.064 (2)	0.056 (2)	−0.0094 (18)	0.0234 (17)	0.0027 (17)
C12	0.065 (2)	0.0435 (17)	0.058 (2)	0.0065 (16)	0.0180 (17)	−0.0001 (15)

Zn1—O2	1.954 (2)	C4—H4	0.9300
Zn1—N1	2.082 (3)	C5—N1	1.347 (5)
Zn1—O1	2.602 (3)	C5—C5i	1.466 (10)
Cl2—C9	1.740 (4)	C6—C11	1.368 (5)
O1—C12	1.233 (4)	C6—C7	1.384 (5)
O2—C12	1.272 (4)	C6—C12	1.506 (5)
C1—N1	1.329 (6)	C7—C8	1.377 (6)
C1—C2	1.377 (6)	C7—H7	0.9300
C1—H1	0.9300	C8—C9	1.368 (6)
C2—C3	1.356 (10)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.368 (5)
C3—C4	1.366 (11)	C10—C11	1.382 (5)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.394 (6)	C11—H11	0.9300
O2—Zn1—O2i	120.76 (15)	C2—C3—C4	119.6 (5)
O2—Zn1—N1	110.75 (11)	C2—C3—H3	120.2
O2i—Zn1—N1	114.15 (11)	C4—C3—H3	120.2
O2—Zn1—N1i	114.15 (11)	C3—C4—C5	119.9 (6)
O2i—Zn1—N1i	110.75 (11)	C3—C4—H4	120.1
N1—Zn1—N1i	78.9 (2)	C5—C4—H4	120.1
O2—Zn1—C12	28.13 (10)	N1—C5—C4	119.6 (5)
O2i—Zn1—C12	107.47 (11)	N1—C5—C5i	115.9 (2)
N1—Zn1—C12	135.29 (12)	C4—C5—C5i	124.5 (4)
N1i—Zn1—C12	101.44 (12)	C1—N1—C5	119.8 (4)
O2—Zn1—C12i	107.47 (11)	C1—N1—Zn1	125.5 (3)
O2i—Zn1—C12i	28.13 (10)	C5—N1—Zn1	114.6 (3)
N1—Zn1—C12i	101.44 (12)	C11—C6—C7	118.8 (3)
N1i—Zn1—C12i	135.29 (12)	C11—C6—C12	120.9 (3)
C12—Zn1—C12i	107.90 (14)	C7—C6—C12	120.3 (3)
O2—Zn1—O1	55.55 (9)	C8—C7—C6	120.9 (4)
O2i—Zn1—O1	91.94 (10)	C8—C7—H7	119.6
N1—Zn1—O1	153.21 (11)	C6—C7—H7	119.6
N1i—Zn1—O1	86.47 (11)	C9—C8—C7	119.0 (4)
C12—Zn1—O1	27.42 (9)	C9—C8—H8	120.5
C12i—Zn1—O1	104.74 (10)	C7—C8—H8	120.5
O2—Zn1—O1i	91.94 (10)	C10—C9—C8	121.2 (4)
O2i—Zn1—O1i	55.55 (9)	C10—C9—Cl2	119.5 (3)
N1—Zn1—O1i	86.47 (11)	C8—C9—Cl2	119.3 (3)
N1i—Zn1—O1i	153.21 (11)	C9—C10—C11	119.3 (4)
C12—Zn1—O1i	104.74 (10)	C9—C10—H10	120.4
C12i—Zn1—O1i	27.42 (9)	C11—C10—H10	120.4
O1—Zn1—O1i	114.90 (12)	C6—C11—C10	120.8 (4)
C12—O1—Zn1	76.2 (2)	C6—C11—H11	119.6
C12—O2—Zn1	105.5 (2)	C10—C11—H11	119.6
N1—C1—C2	122.1 (5)	O1—C12—O2	122.8 (3)
N1—C1—H1	118.9	O1—C12—C6	120.7 (3)
C2—C1—H1	118.9	O2—C12—C6	116.5 (3)
C3—C2—C1	118.9 (6)	O1—C12—Zn1	76.4 (2)
C3—C2—H2	120.5	O2—C12—Zn1	46.41 (16)
C1—C2—H2	120.5	C6—C12—Zn1	162.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.55	3.172 (6)	125
C3—H3···O2ii	0.93	2.52	3.278 (5)	139
C11—H11···O1iii	0.93	2.57	3.330 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.55	3.172 (6)	125
C3—H3⋯O2ii	0.93	2.52	3.278 (5)	139
C11—H11⋯O1iii	0.93	2.57	3.330 (5)	139

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