catena-Poly[[diaqua-(2,2'-bipyridine-κN,N')zinc]-μ-2,2'-[1,4-phenylene-bis(sulfanedi-yl)]diacetato-κO:O'].

In the polymeric title complex, [Zn(C(10)H(8)O(4)S(2))(C(10)H(8)N(2))(H(2)O)(2)](n), the Zn(2+) ion lies on a twofold rotation axis and exhibits an octa-hedral environment, in which it is coordinated by two trans O atoms from two symmetry-related 2,2'-[1,4-phenyl-enebis(sulfanedi-yl)]diacetate anions, two N atoms from one 2,2'-bipyridine ligand, and two cis O atoms from water mol-ecules. The dihedral angle between the two pyridine rings is 11.5 (1)°. Adjacent Zn(2+) ions are bridged in a monodentate manner by the diacetate anions, forming a chain structure extending parallel to [101], and are further linked into the final three-dimensional structure by O-H⋯O hydrogen bonds between the coordinating water mol-ecules as donor and the non-coordinating carboxyl-ate O atoms as acceptor atoms.

Related literature

For background to 1,4-benzene­bis­(thio­acetic acid), including its synthesis and coordination behaviour, see: Yin & Feng (2009 ▶); Yin et al. (2009 ▶); Chen et al. (2010 ▶); Wang et al. (2011 ▶); Jiang et al. (2012 ▶).

Experimental

Crystal data

[Zn(C10H8O4S2)(C10H8N2)(H2O)2]

M = 513.87

Monoclinic,

a = 20.4396 (8) Å

b = 12.8695 (8) Å

c = 7.9798 (4) Å

β = 90.765 (3)°

V = 2098.88 (19) Å3

Z = 4

Mo Kα radiation

μ = 1.41 mm−1

T = 296 K

0.22 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.761, T max = 0.853

16253 measured reflections

2448 independent reflections

2237 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.070

S = 1.04

2448 reflections

147 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Crystal Impact, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055310/wm2568sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055310/wm2568Isup2.hkl

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

[Zn(C10H8O4S2)(C10H8N2)(H2O)2]	F(000) = 1056
Mr = 513.87	Dx = 1.626 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7952 reflections
a = 20.4396 (8) Å	θ = 1.9–27.7°
b = 12.8695 (8) Å	µ = 1.41 mm−1
c = 7.9798 (4) Å	T = 296 K
β = 90.765 (3)°	Block, colourless
V = 2098.88 (19) Å3	0.22 × 0.16 × 0.11 mm
Z = 4

Bruker APEXII CCD diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	2237 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
Tmin = 0.761, Tmax = 0.853	k = −15→16
16253 measured reflections	l = −10→10

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.043P)2 + 0.7442P] where P = (Fo2 + 2Fc2)/3
2448 reflections	(Δ/σ)max = 0.001
147 parameters	Δρmax = 0.31 e Å−3
3 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
Zn1	0.5000	0.725191 (16)	0.2500	0.03569 (9)
S1	0.676748 (19)	0.62114 (4)	0.78141 (5)	0.04863 (12)
N1	0.44065 (7)	0.85617 (9)	0.31662 (16)	0.0391 (3)
O1W	0.57320 (6)	0.61941 (8)	0.18683 (14)	0.0435 (3)
H1WA	0.5703 (10)	0.5693 (13)	0.123 (2)	0.052*
H1WB	0.5785 (10)	0.5933 (15)	0.2793 (18)	0.052*
O1	0.54190 (6)	0.72445 (7)	0.49896 (13)	0.0398 (2)
O2	0.57240 (6)	0.55857 (8)	0.50514 (13)	0.0446 (3)
C1	0.38250 (9)	0.85086 (14)	0.3913 (2)	0.0484 (4)
H1A	0.3633	0.7861	0.4061	0.058*
C2	0.34980 (10)	0.93842 (17)	0.4477 (2)	0.0597 (5)
H2A	0.3089	0.9329	0.4966	0.072*
C3	0.37950 (11)	1.03389 (15)	0.4292 (3)	0.0618 (5)
H3A	0.3594	1.0937	0.4688	0.074*
C4	0.43876 (10)	1.03996 (13)	0.3523 (2)	0.0532 (4)
H4A	0.4592	1.1040	0.3391	0.064*
C5	0.46836 (8)	0.94978 (11)	0.29374 (19)	0.0403 (3)
C6	0.56711 (6)	0.64669 (10)	0.56961 (17)	0.0319 (3)
C7	0.59312 (7)	0.66315 (13)	0.74760 (18)	0.0395 (3)
H7A	0.5652	0.6258	0.8245	0.047*
H7B	0.5901	0.7365	0.7746	0.047*
C8	0.71752 (7)	0.69346 (13)	0.6228 (2)	0.0408 (3)
C9	0.71738 (8)	0.65950 (13)	0.4586 (2)	0.0479 (4)
H9A	0.6958	0.5983	0.4300	0.057*
C10	0.75080 (8)	0.78402 (14)	0.6640 (2)	0.0475 (4)
H10A	0.7518	0.8070	0.7745	0.057*

	U11	U22	U33	U12	U13	U23
Zn1	0.04999 (16)	0.02228 (13)	0.03467 (14)	0.000	−0.00485 (10)	0.000
S1	0.0406 (2)	0.0562 (3)	0.0490 (2)	0.00141 (17)	−0.00659 (17)	0.01881 (18)
N1	0.0518 (7)	0.0284 (6)	0.0367 (6)	0.0019 (5)	−0.0129 (5)	−0.0020 (5)
O1W	0.0664 (7)	0.0291 (5)	0.0349 (5)	0.0064 (5)	−0.0039 (5)	−0.0045 (4)
O1	0.0540 (6)	0.0316 (5)	0.0336 (5)	0.0051 (4)	−0.0085 (5)	−0.0008 (4)
O2	0.0661 (7)	0.0290 (5)	0.0385 (5)	0.0007 (5)	−0.0048 (5)	0.0043 (4)
C1	0.0531 (9)	0.0449 (9)	0.0468 (9)	0.0033 (7)	−0.0084 (7)	−0.0017 (7)
C2	0.0590 (11)	0.0643 (12)	0.0555 (11)	0.0169 (9)	−0.0085 (8)	−0.0076 (9)
C3	0.0744 (13)	0.0478 (10)	0.0626 (11)	0.0254 (9)	−0.0234 (9)	−0.0171 (8)
C4	0.0680 (11)	0.0309 (8)	0.0600 (10)	0.0107 (7)	−0.0274 (9)	−0.0082 (7)
C5	0.0546 (8)	0.0258 (6)	0.0398 (7)	0.0028 (6)	−0.0231 (6)	−0.0023 (5)
C6	0.0324 (6)	0.0328 (7)	0.0304 (6)	−0.0034 (5)	0.0012 (5)	0.0042 (5)
C7	0.0400 (7)	0.0479 (8)	0.0307 (7)	0.0045 (6)	−0.0003 (6)	0.0028 (6)
C8	0.0310 (7)	0.0437 (8)	0.0475 (8)	0.0024 (6)	−0.0010 (6)	0.0051 (7)
C9	0.0418 (8)	0.0454 (9)	0.0564 (10)	−0.0066 (7)	0.0025 (7)	−0.0064 (7)
C10	0.0420 (8)	0.0553 (10)	0.0452 (9)	−0.0039 (7)	0.0003 (7)	−0.0075 (7)

Zn1—O1Wi	2.0896 (11)	C2—C3	1.379 (3)
Zn1—O1W	2.0896 (11)	C2—H2A	0.9300
Zn1—N1i	2.1477 (13)	C3—C4	1.367 (3)
Zn1—N1	2.1477 (13)	C3—H3A	0.9300
Zn1—O1i	2.1529 (10)	C4—C5	1.392 (2)
Zn1—O1	2.1529 (10)	C4—H4A	0.9300
S1—C8	1.7861 (16)	C5—C5i	1.478 (4)
S1—C7	1.8095 (15)	C6—C7	1.5247 (19)
N1—C1	1.339 (2)	C7—H7A	0.9700
N1—C5	1.3447 (19)	C7—H7B	0.9700
O1W—H1WA	0.825 (14)	C8—C9	1.382 (2)
O1W—H1WB	0.817 (14)	C8—C10	1.387 (2)
O1—C6	1.2557 (16)	C9—C10ii	1.388 (2)
O2—C6	1.2506 (17)	C9—H9A	0.9300
C1—C2	1.388 (3)	C10—C9ii	1.388 (2)
C1—H1A	0.9300	C10—H10A	0.9300
O1Wi—Zn1—O1W	98.69 (7)	C1—C2—H2A	120.8
O1Wi—Zn1—N1i	168.43 (5)	C4—C3—C2	119.51 (17)
O1W—Zn1—N1i	92.47 (5)	C4—C3—H3A	120.2
O1Wi—Zn1—N1	92.47 (5)	C2—C3—H3A	120.2
O1W—Zn1—N1	168.43 (5)	C3—C4—C5	119.63 (17)
N1i—Zn1—N1	76.59 (7)	C3—C4—H4A	120.2
O1Wi—Zn1—O1i	86.70 (4)	C5—C4—H4A	120.2
O1W—Zn1—O1i	92.97 (4)	N1—C5—C4	121.03 (16)
N1i—Zn1—O1i	89.66 (4)	N1—C5—C5i	115.91 (9)
N1—Zn1—O1i	90.74 (4)	C4—C5—C5i	123.05 (11)
O1Wi—Zn1—O1	92.97 (4)	O2—C6—O1	125.11 (13)
O1W—Zn1—O1	86.70 (4)	O2—C6—C7	118.57 (12)
N1i—Zn1—O1	90.74 (4)	O1—C6—C7	116.32 (12)
N1—Zn1—O1	89.66 (4)	C6—C7—S1	114.48 (10)
O1i—Zn1—O1	179.49 (5)	C6—C7—H7A	108.6
C8—S1—C7	100.80 (7)	S1—C7—H7A	108.6
C1—N1—C5	118.97 (14)	C6—C7—H7B	108.6
C1—N1—Zn1	125.31 (11)	S1—C7—H7B	108.6
C5—N1—Zn1	115.42 (11)	H7A—C7—H7B	107.6
Zn1—O1W—H1WA	127.8 (14)	C9—C8—C10	119.04 (15)
Zn1—O1W—H1WB	97.9 (14)	C9—C8—S1	120.80 (13)
H1WA—O1W—H1WB	104.3 (17)	C10—C8—S1	120.15 (13)
C6—O1—Zn1	125.00 (9)	C8—C9—C10ii	120.52 (16)
N1—C1—C2	122.49 (17)	C8—C9—H9A	119.7
N1—C1—H1A	118.8	C10ii—C9—H9A	119.7
C2—C1—H1A	118.8	C8—C10—C9ii	120.43 (16)
C3—C2—C1	118.3 (2)	C8—C10—H10A	119.8
C3—C2—H2A	120.8	C9ii—C10—H10A	119.8
O1Wi—Zn1—N1—C1	7.41 (13)	C2—C3—C4—C5	0.0 (3)
O1W—Zn1—N1—C1	−157.1 (2)	C1—N1—C5—C4	2.5 (2)
N1i—Zn1—N1—C1	−176.39 (15)	Zn1—N1—C5—C4	−171.45 (11)
O1i—Zn1—N1—C1	94.13 (13)	C1—N1—C5—C5i	−178.37 (15)
O1—Zn1—N1—C1	−85.55 (13)	Zn1—N1—C5—C5i	7.63 (19)
O1Wi—Zn1—N1—C5	−179.03 (10)	C3—C4—C5—N1	−2.3 (2)
O1W—Zn1—N1—C5	16.4 (3)	C3—C4—C5—C5i	178.72 (18)
N1i—Zn1—N1—C5	−2.82 (7)	Zn1—O1—C6—O2	1.0 (2)
O1i—Zn1—N1—C5	−92.30 (10)	Zn1—O1—C6—C7	−179.21 (9)
O1—Zn1—N1—C5	88.01 (10)	O2—C6—C7—S1	51.79 (17)
O1Wi—Zn1—O1—C6	63.39 (12)	O1—C6—C7—S1	−128.01 (12)
O1W—Zn1—O1—C6	−35.15 (12)	C8—S1—C7—C6	55.61 (13)
N1i—Zn1—O1—C6	−127.58 (12)	C7—S1—C8—C9	−80.93 (14)
N1—Zn1—O1—C6	155.84 (12)	C7—S1—C8—C10	100.14 (14)
O1i—Zn1—O1—C6	14.13 (13)	C10—C8—C9—C10ii	−1.0 (3)
C5—N1—C1—C2	−0.6 (2)	S1—C8—C9—C10ii	−179.94 (13)
Zn1—N1—C1—C2	172.80 (13)	C9—C8—C10—C9ii	1.0 (3)
N1—C1—C2—C3	−1.7 (3)	S1—C8—C10—C9ii	179.95 (13)
C1—C2—C3—C4	1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2iii	0.83 (1)	1.90 (2)	2.7107 (15)	170 (2)
O1W—H1WB···O2	0.82 (1)	1.86 (2)	2.6582 (16)	164 (2)

Table 1

Selected bond lengths (Å)

Zn1—O1W	2.0896 (11)
Zn1—N1	2.1477 (13)
Zn1—O1	2.1529 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2i	0.83 (1)	1.90 (2)	2.7107 (15)	170 (2)
O1W—H1WB⋯O2	0.82 (1)	1.86 (2)	2.6582 (16)	164 (2)

Symmetry code: (i) .