catena-Poly[[(2,2':6',2''-terpyridine-κN,N',N'')zinc(II)]-μ-2,2'-oxydibenzo-ato-κO:O'].

In the title compound, [Zn(C(14)H(8)O(5))(C(15)H(11)N(3))](n), both the Zn(II) ion and the oxydibenzoate ligand are located on a twofold rotation axis. The Zn(II) centre is coordinated by three N atoms from a chelating 2,2':6',2''-terpyridine ligand and two O atoms from two 2,2'-oxydibenzoate ligands, forming a distorted trigonal-bipyramidal coordination environment. Further coordination via the 2,2'-oxydibenzoate anions forms a one-dimensional coordination polymer extending parallel to [010]. Aromatic π-π stacking inter-actions are observed between adjacent terpyridine ligands with a centroid-centroid distance of 3.568 (2) Å.

Related literature

For related structures, see: Zhao & Li (2009 ▶); Andres & Schubert (2004 ▶); Constable (1986 ▶); Hofmeier & Schubert (2004 ▶).

Experimental

Crystal data

[Zn(C14H8O5)(C15H11N3)]

M = 554.84

Orthorhombic,

a = 8.7985 (17) Å

b = 10.694 (2) Å

c = 25.535 (5) Å

V = 2402.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.07 mm−1

T = 296 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.815, T max = 0.847

15388 measured reflections

2924 independent reflections

2347 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.098

S = 1.08

2924 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047679/nk2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047679/nk2011Isup2.hkl

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

[Zn(C14H8O5)(C15H11N3)]	F(000) = 1136
Mr = 554.84	Dx = 1.534 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2235 reflections
a = 8.7985 (17) Å	θ = 2.1–25.4°
b = 10.694 (2) Å	µ = 1.07 mm−1
c = 25.535 (5) Å	T = 296 K
V = 2402.6 (8) Å3	Block, colourless
Z = 4	0.20 × 0.18 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	2924 independent reflections
Radiation source: sealed tube	2347 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 28.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.815, Tmax = 0.847	k = −10→14
15388 measured reflections	l = −27→33

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0319P)2 + 2.226P] where P = (Fo2 + 2Fc2)/3
2924 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.31 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	0.1521 (3)	0.0127 (2)	0.37317 (9)	0.0328 (5)
C2	0.0873 (3)	−0.0769 (2)	0.33333 (8)	0.0279 (5)
C3	−0.0284 (3)	−0.0330 (2)	0.30090 (10)	0.0371 (6)
H3	−0.0602	0.0495	0.3044	0.045*
C4	−0.0974 (3)	−0.1075 (3)	0.26391 (11)	0.0461 (7)
H4	−0.1743	−0.0756	0.2428	0.055*
C5	−0.0514 (3)	−0.2295 (3)	0.25857 (11)	0.0484 (7)
H5	−0.0971	−0.2807	0.2337	0.058*
C6	0.0626 (3)	−0.2760 (2)	0.29012 (11)	0.0428 (6)
H6	0.0930	−0.3589	0.2866	0.051*
C7	0.1323 (3)	−0.2002 (2)	0.32707 (9)	0.0311 (5)
C8	−0.0782 (4)	0.3622 (3)	0.39283 (15)	0.0611 (9)
H8	−0.0598	0.3578	0.3570	0.073*
C9	−0.2154 (4)	0.4118 (4)	0.4104 (2)	0.0781 (12)
H9	−0.2872	0.4412	0.3866	0.094*
C10	−0.2425 (4)	0.4166 (3)	0.4628 (2)	0.0807 (13)
H10	−0.3337	0.4489	0.4752	0.097*
C11	−0.1361 (4)	0.3741 (3)	0.49663 (16)	0.0647 (10)
H11	−0.1540	0.3766	0.5325	0.078*
C12	−0.0007 (3)	0.3269 (2)	0.47753 (11)	0.0450 (7)
C13	0.1247 (3)	0.2844 (2)	0.51128 (10)	0.0437 (7)
C14	0.1214 (5)	0.2817 (3)	0.56602 (12)	0.0699 (11)
H14	0.0327	0.3013	0.5840	0.084*
C15	0.2500	0.2500	0.59255 (18)	0.084 (2)
H15	0.2500	0.2500	0.6290	0.101*
N1	0.2500	0.2500	0.48583 (10)	0.0370 (7)
N2	0.0271 (3)	0.3210 (2)	0.42577 (9)	0.0423 (5)
O3	0.1871 (2)	0.11853 (16)	0.35496 (7)	0.0425 (4)
O4	0.1571 (3)	−0.0158 (2)	0.41919 (8)	0.0732 (8)
O5	0.2500	−0.2500	0.35744 (9)	0.0370 (5)
Zn1	0.2500	0.2500	0.404461 (14)	0.03014 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0402 (13)	0.0278 (13)	0.0305 (12)	0.0013 (10)	−0.0055 (10)	−0.0016 (10)
C2	0.0331 (12)	0.0246 (11)	0.0259 (11)	−0.0057 (10)	0.0003 (9)	0.0003 (8)
C3	0.0432 (14)	0.0287 (13)	0.0395 (13)	−0.0004 (11)	−0.0055 (11)	0.0021 (10)
C4	0.0428 (15)	0.0493 (17)	0.0460 (16)	−0.0070 (13)	−0.0156 (13)	0.0017 (13)
C5	0.0465 (15)	0.0482 (18)	0.0505 (16)	−0.0109 (13)	−0.0102 (13)	−0.0148 (13)
C6	0.0459 (15)	0.0295 (15)	0.0528 (16)	−0.0025 (11)	−0.0031 (13)	−0.0125 (11)
C7	0.0347 (13)	0.0285 (12)	0.0301 (11)	−0.0033 (10)	0.0026 (10)	−0.0012 (9)
C8	0.0508 (18)	0.057 (2)	0.076 (2)	0.0010 (16)	−0.0083 (17)	−0.0014 (17)
C9	0.051 (2)	0.052 (2)	0.132 (4)	0.0036 (16)	−0.014 (2)	−0.005 (2)
C10	0.0508 (19)	0.047 (2)	0.145 (4)	−0.0045 (18)	0.026 (3)	−0.028 (2)
C11	0.059 (2)	0.0445 (19)	0.090 (3)	−0.0147 (16)	0.029 (2)	−0.0232 (17)
C12	0.0480 (16)	0.0293 (14)	0.0577 (17)	−0.0145 (12)	0.0178 (14)	−0.0113 (12)
C13	0.0644 (18)	0.0292 (14)	0.0377 (14)	−0.0192 (12)	0.0137 (13)	−0.0066 (10)
C14	0.120 (3)	0.051 (2)	0.0386 (17)	−0.018 (2)	0.0285 (19)	−0.0064 (13)
C15	0.160 (6)	0.065 (3)	0.028 (2)	−0.020 (4)	0.000	0.000
N1	0.0537 (18)	0.0297 (15)	0.0277 (13)	−0.0183 (15)	0.000	0.000
N2	0.0406 (12)	0.0377 (13)	0.0487 (13)	−0.0046 (10)	0.0024 (10)	−0.0027 (10)
O3	0.0645 (12)	0.0274 (9)	0.0355 (9)	−0.0114 (9)	−0.0081 (9)	−0.0014 (7)
O4	0.134 (2)	0.0536 (14)	0.0323 (11)	−0.0204 (15)	−0.0225 (12)	0.0056 (9)
O5	0.0421 (13)	0.0365 (13)	0.0324 (12)	0.0100 (12)	0.000	0.000
Zn1	0.0392 (2)	0.02603 (19)	0.02521 (19)	−0.00652 (18)	0.000	0.000

C1—O4	1.215 (3)	C10—C11	1.353 (6)
C1—O3	1.261 (3)	C10—H10	0.9300
C1—C2	1.509 (3)	C11—C12	1.383 (4)
C2—C7	1.387 (3)	C11—H11	0.9300
C2—C3	1.394 (3)	C12—N2	1.346 (3)
C3—C4	1.377 (4)	C12—C13	1.472 (4)
C3—H3	0.9300	C13—N1	1.332 (3)
C4—C5	1.372 (4)	C13—C14	1.398 (4)
C4—H4	0.9300	C14—C15	1.362 (5)
C5—C6	1.379 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—C14i	1.362 (5)
C6—C7	1.387 (3)	C15—H15	0.9300
C6—H6	0.9300	N1—C13i	1.332 (3)
C7—O5	1.399 (3)	N1—Zn1	2.078 (3)
C8—N2	1.326 (4)	N2—Zn1	2.172 (2)
C8—C9	1.393 (5)	O3—Zn1	1.9699 (17)
C8—H8	0.9300	O5—C7ii	1.399 (3)
C9—C10	1.360 (6)	Zn1—O3i	1.9699 (17)
C9—H9	0.9300	Zn1—N2i	2.172 (2)
O4—C1—O3	124.9 (2)	C12—C11—H11	120.2
O4—C1—C2	120.4 (2)	N2—C12—C11	121.3 (3)
O3—C1—C2	114.4 (2)	N2—C12—C13	115.1 (2)
C7—C2—C3	117.4 (2)	C11—C12—C13	123.5 (3)
C7—C2—C1	125.0 (2)	N1—C13—C14	119.9 (3)
C3—C2—C1	117.6 (2)	N1—C13—C12	114.8 (2)
C4—C3—C2	122.3 (2)	C14—C13—C12	125.2 (3)
C4—C3—H3	118.8	C15—C14—C13	119.0 (4)
C2—C3—H3	118.8	C15—C14—H14	120.5
C5—C4—C3	119.2 (3)	C13—C14—H14	120.5
C5—C4—H4	120.4	C14—C15—C14i	120.3 (4)
C3—C4—H4	120.4	C14—C15—H15	119.8
C4—C5—C6	119.9 (2)	C14i—C15—H15	119.8
C4—C5—H5	120.0	C13—N1—C13i	121.6 (3)
C6—C5—H5	120.0	C13—N1—Zn1	119.20 (16)
C5—C6—C7	120.5 (2)	C13i—N1—Zn1	119.20 (16)
C5—C6—H6	119.7	C8—N2—C12	118.7 (3)
C7—C6—H6	119.7	C8—N2—Zn1	126.0 (2)
C6—C7—C2	120.5 (2)	C12—N2—Zn1	115.24 (19)
C6—C7—O5	118.8 (2)	C1—O3—Zn1	118.19 (15)
C2—C7—O5	120.6 (2)	C7ii—O5—C7	112.7 (2)
N2—C8—C9	121.9 (4)	O3—Zn1—O3i	100.17 (10)
N2—C8—H8	119.1	O3—Zn1—N1	129.91 (5)
C9—C8—H8	119.1	O3i—Zn1—N1	129.92 (5)
C10—C9—C8	118.9 (4)	O3—Zn1—N2i	99.49 (9)
C10—C9—H9	120.6	O3i—Zn1—N2i	99.01 (9)
C8—C9—H9	120.6	N1—Zn1—N2i	75.49 (6)
C11—C10—C9	119.6 (4)	O3—Zn1—N2	99.01 (9)
C11—C10—H10	120.2	O3i—Zn1—N2	99.49 (9)
C9—C10—H10	120.2	N1—Zn1—N2	75.49 (6)
C10—C11—C12	119.6 (4)	N2i—Zn1—N2	150.99 (12)
C10—C11—H11	120.2
O4—C1—C2—C7	−52.7 (4)	C9—C8—N2—C12	0.4 (5)
O3—C1—C2—C7	132.5 (3)	C9—C8—N2—Zn1	−176.8 (3)
O4—C1—C2—C3	126.2 (3)	C11—C12—N2—C8	0.4 (4)
O3—C1—C2—C3	−48.6 (3)	C13—C12—N2—C8	−177.4 (2)
C7—C2—C3—C4	0.2 (4)	C11—C12—N2—Zn1	177.9 (2)
C1—C2—C3—C4	−178.8 (2)	C13—C12—N2—Zn1	0.1 (3)
C2—C3—C4—C5	0.1 (4)	O4—C1—O3—Zn1	−1.7 (4)
C3—C4—C5—C6	0.1 (4)	C2—C1—O3—Zn1	172.90 (16)
C4—C5—C6—C7	−0.5 (4)	C6—C7—O5—C7ii	55.47 (19)
C5—C6—C7—C2	0.7 (4)	C2—C7—O5—C7ii	−123.7 (2)
C5—C6—C7—O5	−178.5 (2)	C1—O3—Zn1—O3i	173.4 (2)
C3—C2—C7—C6	−0.6 (3)	C1—O3—Zn1—N1	−6.6 (2)
C1—C2—C7—C6	178.3 (2)	C1—O3—Zn1—N2i	72.4 (2)
C3—C2—C7—O5	178.6 (2)	C1—O3—Zn1—N2	−85.2 (2)
C1—C2—C7—O5	−2.5 (4)	C13—N1—Zn1—O3	−86.96 (14)
N2—C8—C9—C10	−0.8 (6)	C13i—N1—Zn1—O3	93.04 (14)
C8—C9—C10—C11	0.4 (6)	C13—N1—Zn1—O3i	93.04 (14)
C9—C10—C11—C12	0.3 (5)	C13i—N1—Zn1—O3i	−86.96 (14)
C10—C11—C12—N2	−0.8 (4)	C13—N1—Zn1—N2i	−177.27 (13)
C10—C11—C12—C13	176.9 (3)	C13i—N1—Zn1—N2i	2.73 (13)
N2—C12—C13—N1	2.2 (3)	C13—N1—Zn1—N2	2.72 (13)
C11—C12—C13—N1	−175.6 (2)	C13i—N1—Zn1—N2	−177.27 (13)
N2—C12—C13—C14	−179.8 (3)	C8—N2—Zn1—O3	−55.0 (3)
C11—C12—C13—C14	2.5 (4)	C12—N2—Zn1—O3	127.67 (18)
N1—C13—C14—C15	3.4 (4)	C8—N2—Zn1—O3i	47.0 (3)
C12—C13—C14—C15	−174.5 (2)	C12—N2—Zn1—O3i	−130.35 (18)
C13—C14—C15—C14i	−1.67 (19)	C8—N2—Zn1—N1	175.9 (3)
C14—C13—N1—C13i	−1.7 (2)	C12—N2—Zn1—N1	−1.39 (17)
C12—C13—N1—C13i	176.5 (2)	C8—N2—Zn1—N2i	175.9 (3)
C14—C13—N1—Zn1	178.3 (2)	C12—N2—Zn1—N2i	−1.39 (17)
C12—C13—N1—Zn1	−3.5 (2)