Bis(μ-2,2'-disulfanediyldibenzoato)bis-[aqua-(2,2'-bipyridine)-nickel(II)].

In the centrosymmetric title complex, [Ni(2)(C(14)H(8)O(4)S(2))(2)(C(10)H(8)N(2))(2)(H(2)O)(2)], the Ni(II) atom is coordinated by two N atoms from one 2,2'-bipyridine ligand, three carboxyl-ate O atoms (one bidentate and one monodentate) from two different disulfanediyldibenzoate ligands and one O atom from a coordinated water mol-ecule in an octa-hedral coordination geometry. The disulfanediyldibenzo-ate dianion bridges two Ni(II )atoms. Adjacent mol-ecules are linked through the coordinated water mol-ecules, forming a O-H⋯O hydrogen-bonded chain running along the a axis.

Related literature

For complexes of 2,2′-disulfanediyldibenzoic acid, see: Feng et al. (2009 ▶); Humphrey et al. (2004 ▶); Li et al. (2007 ▶); Murugavel et al. (2001 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

[Ni2(C14H8O4S2)2(C10H8N2)2(H2O)2]

M = 1074.47

Monoclinic,

a = 13.498 (4) Å

b = 16.769 (5) Å

c = 10.238 (3) Å

β = 93.196 (4)°

V = 2313.7 (12) Å3

Z = 2

Mo Kα radiation

μ = 1.06 mm−1

T = 296 K

0.35 × 0.33 × 0.28 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.708, T max = 0.756

19861 measured reflections

5302 independent reflections

4428 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.06

5302 reflections

307 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002) ▶; cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045824/ng5064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045824/ng5064Isup2.hkl

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

[Ni2(C14H8O4S2)2(C10H8N2)2(H2O)2]	F(000) = 1104
Mr = 1074.47	Dx = 1.542 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7893 reflections
a = 13.498 (4) Å	θ = 2.3–27.5°
b = 16.769 (5) Å	µ = 1.06 mm−1
c = 10.238 (3) Å	T = 296 K
β = 93.196 (4)°	Block, green
V = 2313.7 (12) Å3	0.35 × 0.33 × 0.28 mm
Z = 2

Bruker SMART APEX CCD diffractometer	5302 independent reflections
Radiation source: fine-focus sealed tube	4428 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→17
Tmin = 0.708, Tmax = 0.756	k = −21→20
19861 measured reflections	l = −13→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.5543P] where P = (Fo2 + 2Fc2)/3
5302 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.34 e Å−3
3 restraints	Δρmin = −0.26 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
Ni1	0.847531 (15)	0.055670 (13)	0.87112 (2)	0.035
C1	0.71145 (13)	−0.16433 (10)	0.72485 (16)	0.0372 (4)
C2	0.61332 (13)	−0.15067 (10)	0.75883 (16)	0.0361 (4)
C3	0.54059 (16)	−0.20699 (12)	0.7226 (2)	0.0516 (5)
H3	0.4753	−0.1986	0.7440	0.062*
C4	0.56481 (19)	−0.27532 (13)	0.6549 (2)	0.0630 (6)
H4	0.5157	−0.3124	0.6317	0.076*
C5	0.66066 (19)	−0.28886 (13)	0.6217 (2)	0.0635 (6)
H5	0.6763	−0.3347	0.5760	0.076*
C6	0.73315 (17)	−0.23407 (12)	0.65659 (19)	0.0514 (5)
H6	0.7980	−0.2435	0.6344	0.062*
C7	0.79432 (13)	−0.10570 (11)	0.75377 (16)	0.0375 (4)
C8	0.26979 (12)	0.00106 (10)	0.79602 (16)	0.0364 (4)
C9	0.37029 (12)	−0.01665 (10)	0.77860 (15)	0.0352 (3)
C10	0.41443 (15)	0.01522 (13)	0.67009 (18)	0.0493 (5)
H10	0.4808	0.0044	0.6576	0.059*
C11	0.36100 (17)	0.06275 (15)	0.5808 (2)	0.0609 (6)
H11	0.3919	0.0836	0.5094	0.073*
C12	0.26263 (17)	0.07935 (15)	0.5966 (2)	0.0631 (6)
H12	0.2268	0.1108	0.5359	0.076*
C13	0.21750 (15)	0.04884 (13)	0.70385 (19)	0.0509 (5)
H13	0.1511	0.0603	0.7149	0.061*
C14	0.21825 (12)	−0.02608 (10)	0.91345 (16)	0.0345 (3)
O1	0.76966 (9)	−0.04232 (7)	0.81054 (13)	0.0430 (3)
O2	0.87892 (10)	−0.12087 (10)	0.71985 (16)	0.0652 (4)
O3	0.26151 (9)	−0.07316 (7)	0.99322 (11)	0.0361 (3)
O4	0.13146 (8)	−0.00058 (8)	0.93571 (12)	0.0437 (3)
S1	0.58588 (3)	−0.06272 (3)	0.85144 (4)	0.03707 (9)
S2	0.44006 (3)	−0.07593 (3)	0.89692 (4)	0.03871 (10)
C15	0.71731 (16)	0.10390 (13)	0.6351 (2)	0.0548 (5)
H15	0.7039	0.0497	0.6255	0.066*
C16	0.66890 (17)	0.15698 (15)	0.5504 (2)	0.0650 (6)
H16	0.6246	0.1389	0.4841	0.078*
C17	0.68751 (18)	0.23695 (15)	0.5661 (2)	0.0652 (6)
H17	0.6560	0.2739	0.5103	0.078*
C18	0.75337 (18)	0.26211 (13)	0.6655 (2)	0.0577 (5)
H18	0.7656	0.3162	0.6782	0.069*
C19	0.80122 (14)	0.20630 (11)	0.74626 (18)	0.0430 (4)
C20	0.87518 (14)	0.22631 (11)	0.85377 (18)	0.0441 (4)
C21	0.90507 (19)	0.30399 (14)	0.8850 (2)	0.0629 (6)
H21	0.8783	0.3471	0.8380	0.075*
C22	0.9751 (2)	0.31585 (16)	0.9869 (3)	0.0739 (7)
H22	0.9951	0.3673	1.0099	0.089*
C23	1.01454 (18)	0.25211 (16)	1.0536 (2)	0.0671 (6)
H23	1.0621	0.2593	1.1219	0.081*
C24	0.98269 (15)	0.17672 (14)	1.0180 (2)	0.0564 (5)
H24	1.0101	0.1332	1.0631	0.068*
N1	0.78256 (11)	0.12735 (9)	0.73016 (14)	0.0413 (3)
N2	0.91367 (11)	0.16354 (9)	0.92081 (15)	0.0432 (3)
O5	0.96680 (9)	0.01730 (9)	0.77302 (14)	0.0491 (3)
H5A	1.0177 (12)	0.0183 (13)	0.824 (2)	0.074*
H5B	0.9511 (17)	−0.0306 (7)	0.754 (2)	0.074*

	U11	U22	U33	U12	U13	U23
Ni1	0.026	0.039	0.040	−0.001	0.003	0.007
C1	0.0405 (9)	0.0373 (9)	0.0332 (8)	0.0051 (7)	−0.0024 (7)	0.0006 (7)
C2	0.0394 (9)	0.0346 (9)	0.0338 (8)	0.0004 (7)	−0.0025 (7)	0.0028 (6)
C3	0.0476 (11)	0.0493 (11)	0.0572 (11)	−0.0082 (9)	−0.0033 (9)	−0.0062 (9)
C4	0.0699 (15)	0.0470 (12)	0.0703 (14)	−0.0087 (11)	−0.0129 (12)	−0.0120 (10)
C5	0.0832 (17)	0.0434 (12)	0.0624 (13)	0.0081 (11)	−0.0098 (12)	−0.0160 (10)
C6	0.0570 (12)	0.0489 (11)	0.0476 (10)	0.0123 (10)	−0.0028 (9)	−0.0067 (9)
C7	0.0341 (9)	0.0441 (10)	0.0340 (8)	0.0070 (7)	0.0008 (7)	0.0009 (7)
C8	0.0318 (8)	0.0419 (9)	0.0356 (8)	−0.0026 (7)	0.0020 (7)	−0.0001 (7)
C9	0.0343 (8)	0.0380 (9)	0.0333 (8)	−0.0011 (7)	0.0009 (6)	−0.0010 (7)
C10	0.0398 (10)	0.0672 (13)	0.0416 (9)	0.0035 (9)	0.0100 (8)	0.0056 (9)
C11	0.0549 (13)	0.0874 (17)	0.0411 (10)	0.0048 (11)	0.0106 (9)	0.0210 (10)
C12	0.0552 (13)	0.0885 (17)	0.0455 (11)	0.0112 (12)	0.0017 (10)	0.0251 (11)
C13	0.0362 (10)	0.0692 (14)	0.0474 (10)	0.0067 (9)	0.0025 (8)	0.0131 (9)
C14	0.0282 (8)	0.0361 (8)	0.0392 (8)	−0.0051 (7)	0.0015 (7)	−0.0012 (7)
O1	0.0318 (6)	0.0405 (7)	0.0576 (7)	−0.0019 (5)	0.0097 (6)	−0.0059 (6)
O2	0.0349 (7)	0.0753 (11)	0.0862 (11)	0.0066 (7)	0.0110 (7)	−0.0292 (9)
O3	0.0303 (6)	0.0369 (6)	0.0414 (6)	−0.0006 (5)	0.0051 (5)	0.0039 (5)
O4	0.0268 (6)	0.0562 (8)	0.0483 (7)	0.0033 (5)	0.0052 (5)	0.0090 (6)
S1	0.0287 (2)	0.0389 (2)	0.0437 (2)	−0.00063 (17)	0.00326 (17)	−0.00318 (18)
S2	0.0290 (2)	0.0452 (2)	0.0422 (2)	−0.00065 (18)	0.00338 (17)	0.00589 (18)
C15	0.0550 (12)	0.0520 (12)	0.0560 (12)	0.0005 (10)	−0.0092 (9)	0.0086 (9)
C16	0.0598 (14)	0.0721 (16)	0.0610 (13)	0.0092 (12)	−0.0150 (11)	0.0087 (11)
C17	0.0726 (16)	0.0638 (15)	0.0585 (13)	0.0257 (12)	−0.0014 (11)	0.0158 (11)
C18	0.0692 (14)	0.0450 (11)	0.0594 (12)	0.0142 (10)	0.0079 (10)	0.0108 (9)
C19	0.0429 (10)	0.0420 (10)	0.0453 (9)	0.0038 (8)	0.0128 (8)	0.0075 (8)
C20	0.0432 (10)	0.0435 (10)	0.0470 (10)	−0.0060 (8)	0.0150 (8)	0.0060 (8)
C21	0.0758 (16)	0.0470 (12)	0.0670 (14)	−0.0151 (11)	0.0128 (12)	0.0067 (10)
C22	0.0807 (18)	0.0650 (16)	0.0771 (16)	−0.0348 (14)	0.0130 (14)	−0.0062 (13)
C23	0.0585 (14)	0.0775 (17)	0.0652 (14)	−0.0287 (13)	0.0014 (11)	−0.0046 (12)
C24	0.0410 (11)	0.0672 (14)	0.0604 (12)	−0.0145 (10)	−0.0024 (9)	0.0069 (10)
N1	0.0360 (8)	0.0433 (8)	0.0444 (8)	0.0004 (7)	0.0023 (6)	0.0083 (7)
N2	0.0338 (8)	0.0477 (9)	0.0487 (8)	−0.0080 (7)	0.0068 (6)	0.0061 (7)
O5	0.0286 (7)	0.0674 (9)	0.0516 (8)	0.0012 (6)	0.0054 (5)	0.0055 (7)

Ni1—O1	2.0290 (13)	C12—H12	0.9300
Ni1—N1	2.0385 (15)	C13—H13	0.9300
Ni1—O5	2.0481 (14)	C14—O3	1.256 (2)
Ni1—N2	2.0682 (16)	C14—O4	1.279 (2)
Ni1—O3i	2.0999 (13)	C14—Ni1i	2.4734 (18)
Ni1—O4i	2.1869 (13)	O3—Ni1i	2.0999 (13)
Ni1—C14i	2.4733 (18)	O4—Ni1i	2.1870 (13)
C1—C6	1.402 (3)	S1—S2	2.0596 (8)
C1—C2	1.407 (2)	C15—N1	1.335 (2)
C1—C7	1.506 (2)	C15—C16	1.381 (3)
C2—C3	1.398 (2)	C15—H15	0.9300
C2—S1	1.8029 (18)	C16—C17	1.372 (3)
C3—C4	1.387 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.379 (3)
C4—C5	1.375 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.385 (3)
C5—C6	1.375 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—N1	1.356 (2)
C6—H6	0.9300	C19—C20	1.483 (3)
C7—O2	1.238 (2)	C20—N2	1.345 (2)
C7—O1	1.265 (2)	C20—C21	1.395 (3)
C8—C13	1.399 (2)	C21—C22	1.383 (3)
C8—C9	1.410 (2)	C21—H21	0.9300
C8—C14	1.493 (2)	C22—C23	1.361 (4)
C9—C10	1.396 (2)	C22—H22	0.9300
C9—S2	1.7932 (17)	C23—C24	1.378 (3)
C10—C11	1.385 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—N2	1.343 (2)
C11—C12	1.375 (3)	C24—H24	0.9300
C11—H11	0.9300	O5—H5A	0.841 (9)
C12—C13	1.383 (3)	O5—H5B	0.850 (9)
O1—Ni1—N1	93.79 (6)	C11—C12—H12	120.3
O1—Ni1—O5	90.21 (6)	C13—C12—H12	120.3
N1—Ni1—O5	99.03 (6)	C12—C13—C8	121.29 (19)
O1—Ni1—N2	173.06 (6)	C12—C13—H13	119.4
N1—Ni1—N2	79.70 (6)	C8—C13—H13	119.4
O5—Ni1—N2	93.16 (6)	O3—C14—O4	119.43 (15)
O1—Ni1—O3i	86.85 (5)	O3—C14—C8	119.62 (15)
N1—Ni1—O3i	95.52 (6)	O4—C14—C8	120.92 (15)
O5—Ni1—O3i	165.32 (5)	O3—C14—Ni1i	58.08 (9)
N2—Ni1—O3i	91.37 (5)	O4—C14—Ni1i	62.00 (9)
O1—Ni1—O4i	88.47 (5)	C8—C14—Ni1i	170.27 (12)
N1—Ni1—O4i	156.68 (6)	C7—O1—Ni1	132.52 (12)
O5—Ni1—O4i	104.18 (5)	C14—O3—Ni1i	91.41 (10)
N2—Ni1—O4i	96.58 (6)	C14—O4—Ni1i	86.90 (10)
O3i—Ni1—O4i	61.39 (5)	C2—S1—S2	104.94 (6)
O1—Ni1—C14i	84.52 (5)	C9—S2—S1	105.08 (6)
N1—Ni1—C14i	126.01 (6)	N1—C15—C16	122.5 (2)
O5—Ni1—C14i	134.86 (6)	N1—C15—H15	118.7
N2—Ni1—C14i	97.33 (6)	C16—C15—H15	118.7
O3i—Ni1—C14i	30.51 (5)	C17—C16—C15	118.6 (2)
O4i—Ni1—C14i	31.10 (5)	C17—C16—H16	120.7
C6—C1—C2	119.01 (17)	C15—C16—H16	120.7
C6—C1—C7	117.97 (17)	C16—C17—C18	119.46 (19)
C2—C1—C7	122.97 (15)	C16—C17—H17	120.3
C3—C2—C1	118.77 (17)	C18—C17—H17	120.3
C3—C2—S1	122.05 (15)	C17—C18—C19	119.6 (2)
C1—C2—S1	119.15 (13)	C17—C18—H18	120.2
C4—C3—C2	120.6 (2)	C19—C18—H18	120.2
C4—C3—H3	119.7	N1—C19—C18	120.67 (19)
C2—C3—H3	119.7	N1—C19—C20	115.09 (16)
C5—C4—C3	120.7 (2)	C18—C19—C20	124.23 (19)
C5—C4—H4	119.6	N2—C20—C21	121.00 (19)
C3—C4—H4	119.6	N2—C20—C19	115.26 (16)
C4—C5—C6	119.4 (2)	C21—C20—C19	123.75 (19)
C4—C5—H5	120.3	C22—C21—C20	118.9 (2)
C6—C5—H5	120.3	C22—C21—H21	120.5
C5—C6—C1	121.4 (2)	C20—C21—H21	120.5
C5—C6—H6	119.3	C23—C22—C21	119.8 (2)
C1—C6—H6	119.3	C23—C22—H22	120.1
O2—C7—O1	124.88 (17)	C21—C22—H22	120.1
O2—C7—C1	119.81 (17)	C22—C23—C24	118.7 (2)
O1—C7—C1	115.29 (15)	C22—C23—H23	120.7
C13—C8—C9	119.23 (16)	C24—C23—H23	120.7
C13—C8—C14	118.52 (16)	N2—C24—C23	122.7 (2)
C9—C8—C14	122.18 (15)	N2—C24—H24	118.6
C10—C9—C8	118.46 (16)	C23—C24—H24	118.6
C10—C9—S2	121.23 (14)	C15—N1—C19	119.12 (16)
C8—C9—S2	120.27 (13)	C15—N1—Ni1	125.65 (14)
C11—C10—C9	121.06 (18)	C19—N1—Ni1	114.83 (12)
C11—C10—H10	119.5	C24—N2—C20	118.79 (18)
C9—C10—H10	119.5	C24—N2—Ni1	126.75 (14)
C12—C11—C10	120.63 (19)	C20—N2—Ni1	114.19 (12)
C12—C11—H11	119.7	Ni1—O5—H5A	108.9 (17)
C10—C11—H11	119.7	Ni1—O5—H5B	102.6 (18)
C11—C12—C13	119.32 (19)	H5A—O5—H5B	110.3 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O2	0.85 (1)	1.82 (1)	2.646 (2)	162 (2)
O5—H5A···O4ii	0.84 (1)	1.89 (1)	2.7187 (18)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O2	0.85 (1)	1.82 (1)	2.646 (2)	162 (2)
O5—H5A⋯O4i	0.84 (1)	1.89 (1)	2.7187 (18)	169 (2)

Symmetry code: (i) .