catena-Poly[[bis-(2-hydr-oxy-2-phenyl-acetato-κO,O)zinc(II)]-μ-1,2-di-4-pyridylethane-κN:N'].

The title compound, [Zn(C(8)H(6)O(3))(2)(C(12)H(12)N(2))](n), consists of [Zn(Hopa)(2)] (H(2)opa = 2-hydr-oxy-2-phenyl-acetic acid or mandelic acid) units bridged by 1,2-di-4-pyridylethane (bpe) ligands, forming a polymeric chain developing parallel to the b axis. The bridging bpe ligand is arranged around a twofold axis passing through the middle of the ethane C-C bond. The geometry around the Zn(II) ion is distorted octa-hedral, constructed by four O atoms from two Hopa(-) ligands and two N atoms from two bridging bpe ligands. O-H⋯O hydrogen bonds link the chains, forming a three-dimensional network.

Related literature

Transition metal ions are the major cationic contributors to the inorganic composition of natural water and biological fluids, see: Daniele et al. (2008 ▶). For related structures, see: Balboa et al. (2008 ▶); Beghidja et al. (2005 ▶); Hao et al. (2009 ▶); Lee et al. (2008 ▶); Park et al. (2008 ▶); Shin et al. (2009 ▶); Wermester et al. (2007 ▶); Yu et al. (2008 ▶).

Experimental

Crystal data

[Zn(C8H6O3)2(C12H12N2)]

M = 551.90

Hexagonal,

a = 11.1360 (6) Å

c = 33.110 (3) Å

V = 3555.9 (4) Å3

Z = 6

Mo Kα radiation

μ = 1.09 mm−1

T = 293 K

0.10 × 0.05 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.933, T max = 0.944

17715 measured reflections

2347 independent reflections

2045 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.068

S = 1.04

2347 reflections

168 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 870 Friedel pairs

Flack parameter: −0.002 (16)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030281/dn2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030281/dn2478Isup2.hkl

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

[Zn(C8H6O3)2(C12H12N2)]	Dx = 1.546 Mg m−3
Mr = 551.90	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P6122	Cell parameters from 1751 reflections
Hall symbol: P 61 2 (0 0 -1)	θ = 2.2–18.9°
a = 11.1360 (6) Å	µ = 1.09 mm−1
c = 33.110 (3) Å	T = 293 K
V = 3555.9 (4) Å3	Rod, colorless
Z = 6	0.10 × 0.05 × 0.05 mm
F(000) = 1716

Bruker SMART CCD diffractometer	2347 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
graphite	Rint = 0.077
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.933, Tmax = 0.944	k = −11→13
17715 measured reflections	l = −40→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.016P)2 + 1.0575P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2347 reflections	Δρmax = 0.22 e Å−3
168 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 870 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.002 (16)

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 > 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	0.73603 (4)	0.86802 (2)	0.0833	0.01944 (12)
O11	0.76202 (18)	0.84579 (18)	0.02239 (5)	0.0216 (4)
O12	0.89644 (18)	0.82448 (18)	−0.02384 (5)	0.0245 (5)
O13	0.89365 (17)	0.81243 (17)	0.08319 (5)	0.0233 (4)
H13O	0.9568	0.8433	0.1013	0.035*
N21	0.5928 (2)	0.9386 (2)	0.07376 (7)	0.0223 (5)
C11	0.8619 (3)	0.8302 (2)	0.01183 (8)	0.0191 (6)
C12	0.9540 (3)	0.8194 (3)	0.04470 (8)	0.0179 (6)
H12	1.0448	0.9043	0.0438	0.022*
C13	0.9761 (3)	0.6975 (3)	0.03869 (8)	0.0201 (6)
C14	1.1078 (3)	0.7159 (3)	0.03588 (9)	0.0284 (7)
H14	1.1839	0.8052	0.0368	0.034*
C15	1.1293 (4)	0.6038 (4)	0.03167 (10)	0.0394 (8)
H15	1.2189	0.6185	0.0295	0.047*
C16	1.0181 (4)	0.4716 (4)	0.03078 (10)	0.0423 (9)
H16	1.0316	0.3960	0.0283	0.051*
C17	0.8862 (4)	0.4520 (3)	0.03359 (9)	0.0382 (8)
H17	0.8105	0.3624	0.0328	0.046*
C18	0.8639 (3)	0.5636 (3)	0.03754 (8)	0.0280 (6)
H18	0.7741	0.5486	0.0394	0.034*
C21	0.6235 (3)	1.0429 (3)	0.04786 (9)	0.0310 (8)
H21	0.7018	1.0742	0.0317	0.037*
C22	0.5445 (3)	1.1057 (3)	0.04412 (10)	0.0357 (8)
H22	0.5682	1.1757	0.0252	0.043*
C23	0.4294 (3)	1.0642 (3)	0.06862 (10)	0.0289 (7)
C24	0.4001 (3)	0.9599 (3)	0.09618 (9)	0.0288 (7)
H24	0.3251	0.9299	0.1136	0.035*
C25	0.4832 (3)	0.9009 (3)	0.09751 (8)	0.0252 (6)
H25	0.4613	0.8304	0.1161	0.030*
C26	0.3364 (3)	1.1263 (3)	0.06523 (12)	0.0520 (11)
H26A	0.2422	1.0517	0.0607	0.062*
H26B	0.3641	1.1857	0.0416	0.062*

	U11	U22	U33	U12	U13	U23
Zn1	0.0209 (2)	0.01972 (17)	0.0181 (2)	0.01044 (12)	0.000	−0.00108 (18)
O11	0.0248 (10)	0.0247 (10)	0.0185 (10)	0.0148 (8)	−0.0010 (8)	0.0008 (8)
O12	0.0311 (12)	0.0325 (11)	0.0154 (10)	0.0200 (9)	0.0007 (9)	0.0017 (8)
O13	0.0270 (10)	0.0352 (10)	0.0135 (9)	0.0198 (9)	−0.0050 (9)	−0.0048 (8)
N21	0.0218 (12)	0.0224 (12)	0.0213 (14)	0.0101 (10)	0.0011 (10)	0.0006 (10)
C11	0.0231 (13)	0.0141 (14)	0.0176 (15)	0.0074 (12)	−0.0024 (13)	−0.0004 (11)
C12	0.0190 (13)	0.0189 (13)	0.0142 (14)	0.0083 (10)	−0.0012 (11)	−0.0025 (11)
C13	0.0274 (15)	0.0231 (15)	0.0113 (13)	0.0137 (12)	−0.0034 (11)	0.0004 (12)
C14	0.0297 (17)	0.0309 (16)	0.0296 (18)	0.0189 (14)	−0.0055 (13)	−0.0065 (14)
C15	0.048 (2)	0.057 (2)	0.0319 (19)	0.040 (2)	−0.0055 (17)	−0.0054 (17)
C16	0.080 (3)	0.049 (2)	0.0260 (18)	0.053 (2)	−0.0044 (18)	−0.0044 (16)
C17	0.062 (2)	0.0242 (17)	0.0226 (17)	0.0172 (17)	−0.0001 (16)	−0.0020 (14)
C18	0.0350 (16)	0.0237 (16)	0.0215 (15)	0.0117 (14)	−0.0015 (14)	−0.0003 (13)
C21	0.0241 (16)	0.0359 (18)	0.0286 (18)	0.0118 (14)	0.0005 (13)	0.0089 (14)
C22	0.0329 (18)	0.0310 (18)	0.0393 (19)	0.0131 (16)	−0.0083 (15)	0.0094 (14)
C23	0.0298 (17)	0.0265 (15)	0.0344 (19)	0.0172 (14)	−0.0179 (14)	−0.0153 (14)
C24	0.0275 (17)	0.0359 (18)	0.0293 (17)	0.0206 (14)	0.0010 (13)	−0.0039 (14)
C25	0.0306 (16)	0.0239 (16)	0.0219 (15)	0.0143 (12)	0.0033 (13)	0.0018 (12)
C26	0.039 (2)	0.0319 (17)	0.093 (3)	0.0242 (16)	−0.0356 (19)	−0.0234 (19)

Zn1—O11	2.0707 (17)	C15—C16	1.371 (5)
Zn1—O11i	2.0707 (17)	C15—H15	0.9300
Zn1—N21	2.125 (2)	C16—C17	1.376 (5)
Zn1—N21i	2.125 (2)	C16—H16	0.9300
Zn1—O13i	2.1332 (17)	C17—C18	1.390 (4)
Zn1—O13	2.1332 (17)	C17—H17	0.9300
O11—C11	1.258 (3)	C18—H18	0.9300
O12—C11	1.254 (3)	C21—C22	1.376 (4)
O13—C12	1.425 (3)	C21—H21	0.9300
O13—H13O	0.8543	C22—C23	1.386 (4)
N21—C25	1.332 (3)	C22—H22	0.9300
N21—C21	1.344 (3)	C23—C24	1.381 (4)
C11—C12	1.541 (4)	C23—C26	1.511 (4)
C12—C13	1.509 (4)	C24—C25	1.378 (4)
C12—H12	0.9800	C24—H24	0.9300
C13—C14	1.379 (4)	C25—H25	0.9300
C13—C18	1.387 (4)	C26—C26ii	1.519 (7)
C14—C15	1.390 (4)	C26—H26A	0.9700
C14—H14	0.9300	C26—H26B	0.9700
O11—Zn1—O11i	166.10 (10)	C13—C14—H14	119.3
O11—Zn1—N21	94.27 (8)	C15—C14—H14	119.3
O11i—Zn1—N21	94.75 (8)	C16—C15—C14	119.8 (3)
O11—Zn1—N21i	94.75 (8)	C16—C15—H15	120.1
O11i—Zn1—N21i	94.27 (8)	C14—C15—H15	120.1
N21—Zn1—N21i	98.92 (11)	C15—C16—C17	119.3 (3)
O11—Zn1—O13i	92.80 (7)	C15—C16—H16	120.4
O11i—Zn1—O13i	77.21 (7)	C17—C16—H16	120.4
N21—Zn1—O13i	86.60 (7)	C16—C17—C18	121.2 (3)
N21i—Zn1—O13i	170.28 (8)	C16—C17—H17	119.4
O11—Zn1—O13	77.21 (7)	C18—C17—H17	119.4
O11i—Zn1—O13	92.80 (7)	C13—C18—C17	119.8 (3)
N21—Zn1—O13	170.28 (8)	C13—C18—H18	120.1
N21i—Zn1—O13	86.60 (7)	C17—C18—H18	120.1
O13i—Zn1—O13	89.11 (9)	N21—C21—C22	123.1 (3)
C11—O11—Zn1	118.26 (16)	N21—C21—H21	118.5
C12—O13—Zn1	114.85 (15)	C22—C21—H21	118.5
C12—O13—H13O	109.5	C21—C22—C23	119.8 (3)
Zn1—O13—H13O	120.8	C21—C22—H22	120.1
C25—N21—C21	116.5 (2)	C23—C22—H22	120.1
C25—N21—Zn1	122.35 (18)	C24—C23—C22	117.2 (3)
C21—N21—Zn1	120.11 (19)	C24—C23—C26	120.4 (3)
O12—C11—O11	125.7 (3)	C22—C23—C26	122.4 (3)
O12—C11—C12	115.4 (2)	C25—C24—C23	119.3 (3)
O11—C11—C12	118.9 (2)	C25—C24—H24	120.4
O13—C12—C13	110.7 (2)	C23—C24—H24	120.4
O13—C12—C11	108.8 (2)	N21—C25—C24	124.0 (3)
C13—C12—C11	113.0 (2)	N21—C25—H25	118.0
O13—C12—H12	108.1	C24—C25—H25	118.0
C13—C12—H12	108.1	C23—C26—C26ii	115.7 (3)
C11—C12—H12	108.1	C23—C26—H26A	108.4
C14—C13—C18	118.5 (3)	C26ii—C26—H26A	108.4
C14—C13—C12	121.0 (3)	C23—C26—H26B	108.4
C18—C13—C12	120.4 (2)	C26ii—C26—H26B	108.4
C13—C14—C15	121.4 (3)	H26A—C26—H26B	107.4

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13O···O12iii	0.85	1.77	2.619 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13O⋯O12i	0.85	1.77	2.619 (3)	173

Symmetry code: (i) .