catena-Poly[[(2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)zinc(II)]-μ-2,2′-oxydibenzo­ato-κ2O:O′]

Gong, H.-Y.; Bai, Y.; Liu, W.

doi:10.1107/S1600536809047679

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1589

doi:10.1107/S1600536809047679

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catena-Poly[[(2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)zinc(II)]-μ-2,2′-oxydibenzoato-κ²O:O′]

Hai-Yan Gong,^a ^* Yan Bai ^a and Wei Liu ^a

^aThe Center of Analysis and Determination, Henan University of Traditional Chinese Medicine, No. 1 Jinshui Road, Zhengzhou 450008, Henan, People's Republic of China
^*Correspondence e-mail: haiyangong@yeah.net

(Received 20 October 2009; accepted 11 November 2009; online 14 November 2009)

In the title compound, [Zn(C₁₄H₈O₅)(C₁₅H₁₁N₃)]_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 interactions 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_r = 554.84
Orthorhombic, P c c n
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.098
S = 1.08
2924 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

2,2':6',2''-Terpyridine and its derivatives have been intensively explored because of the interesting electronic, photonic, magnetic, reactive and structural properties shown by the transition metal complexes of these ligands (Andres & Schubert, 2004; Constable, 1986; Hofmeier & Schubert, 2004). We report here the synthesis and structure of the Zn^II complex based on the 2,2':6',2''-terpyridine ligand.

In the crystal structure of the title compound, the Zn atoms are coordinated by three N atoms from a chelating terpy ligand and two O atoms from two 2,2'-oxydibenzoate ligands, forming a distorted trigonal bipyramidal coordination environment (Figure 1). The Zinc atoms are linked by the 2,2-oxydibenzoate anions into a one-dimensional coordination polymer.

Aromatic stacking interactions between Cg1 and Cg2 [Cg1 and Cg2 are (N2, C8 – C12) and (N2ⁱ, C8ⁱ – C12ⁱ) ring centroids, respectively, symmetry code:(i) -1/2 - x,1/2 - y,z] are observed, with a centroid–centroid distances of 3.568 (2) Å.

Related literature top

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

Experimental top

The title complound was synthesized hydrothermally in a Teflon-lined autoclave (25 ml) by heating a mixture of 2,2':6',2''-terpyridine (0.2 mmol), 2,2'-oxydibenzoic acid (0.4 mmol) and ZnSO₄.H₂O (0.2 mmol) in water (10 ml) at 393 K for 3 d. The autoclave was slowly cooled to room temperature. Crystals suitable for X-ray analysis were obtained.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. [Symmetry codes: (i) -x+1/2, -y+1/2, z; (ii) -x+1/2, -y-1/2, z.]

catena-Poly[[(2,2':6',2''-terpyridine- κ³N,N',N'')zinc(II)]-µ-2,2'-oxydibenzoato- κ²O:O'] top

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₅H₁₁N₃)]	F(000) = 1136
M_r = 554.84	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0319P)² + 2.226P] where P = (F_o² + 2F_c²)/3
2924 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Zn(C₁₄H₈O₅)(C₁₅H₁₁N₃)]	V = 2402.6 (8) Å³
M_r = 554.84	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 8.7985 (17) Å	µ = 1.07 mm⁻¹
b = 10.694 (2) Å	T = 296 K
c = 25.535 (5) Å	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2924 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2347 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.847	R_int = 0.043
15388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.08	Δρ_max = 0.39 e Å⁻³
2924 reflections	Δρ_min = −0.31 e Å⁻³
174 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1/2, −y+1/2, z; (ii) −x+1/2, −y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₈O₅)(C₁₅H₁₁N₃)]
M_r	554.84
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	296
a, b, c (Å)	8.7985 (17), 10.694 (2), 25.535 (5)
V (Å³)	2402.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.815, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	15388, 2924, 2347
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.098, 1.08
No. of reflections	2924
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

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