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

Liu, Z.; Qu, B.; Yu, J.; Yuan, L.; Liu, W.

doi:10.1107/S1600536810045824

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1563

https://doi.org/10.1107/S1600536810045824

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

Zhengming Liu,^a Botao Qu,^b Jianghua Yu,^b Limin Yuan ^a and Wenlong Liu ^b ^*

^aTesting Center, Yangzhou Universitry, Yangzhou, 225002, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Yangzhou Universitry, Yangzhou, 225002, People's Republic of China
^*Correspondence e-mail: liuwl@yzu.edu.cn

(Received 7 November 2010; accepted 8 November 2010; online 13 November 2010)

In the centrosymmetric title complex, [Ni₂(C₁₄H₈O₄S₂)₂(C₁₀H₈N₂)₂(H₂O)₂], the Ni^II atom is coordinated by two N atoms from one 2,2′-bipyridine ligand, three carboxylate O atoms (one bidentate and one monodentate) from two different disulfanediyldibenzoate ligands and one O atom from a coordinated water molecule in an octahedral coordination geometry. The disulfanediyldibenzoate dianion bridges two Ni^IIatoms. Adjacent molecules are linked through the coordinated water molecules, 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_r = 1074.47
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.06
5302 reflections
307 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) x+1, y, z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045824/ng5064Isup2.hkl

checkCIF report

Comment top

The flexible 2,2'-disulfanediyldibenzoic acid, a multifunctional ligand containing both carboxylic and thio groups, can potentially afford various coordination modes and diverse coordination architectures. Many complexes with this ligand show unique structural topologies and interesting properties (Murugavel et al., 2001; Humphrey et al., 2004; Li et al., 2007; Zhou et al., 2009; Feng et al., 2009). In this work, we have used this ligand to react with a Ni^II salt in the presence of 2,2'-bipyridine as a chelating co-ligand, to obtain the title binuclear compound, Ni₂(H₂O)₂(C₁₀H₈N₂)₂(C₁₄H₈O₄S₂)₂.

The asymmetric unit of the title compound is composed of one Ni^II ion, one 2,2'-disulfanediyldibenzoate ligand, one 2,2'-bipyridine ligand and one coordinated water molecule (Fig. 1). The Ni^II center is six-coordinated, in a distorted octahedral geometry, by two N atoms from one 2,2'-bipyridine ligand, three carboxylate O atoms from two different disulfanediyldibenzoate ligands and one O atom from a coordinated water molecule Two disulfanediyldibenzoate dianions bridge two Ni^IIions about a center of inversion with its two carboxylate groups in bidentate chelating and monodentate modes, respectively, generating the title binuclear compound. The Ni···Ni distance bridged by two 2, 2'-disulfanediyldibenzoate is 10.061 (3) Å. Adjacent molecules are linked through both O5—H5A···O2 and O5—H5B···O4(x + 1, y, z) hydrogen bonds and lead to the formation of a one-dimensional hydrogen-bonded chain running along the a axis (Fig. 2).

Related literature top

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 top

A mixture of Ni(NO₃)₂.6H₂O (21.0 mg, 0.1 mmol) with 2,2'-disulfanediyldibenzoic acid (30.6 mg, 0.1 mmol), 2,2'-bipyridine (15.6 mg, 0.1 mmol) and water (10 ml) was sealed in a 25 ml Teflon-lined stainless steel vessel, and heated at 383 K for 3 d. A number of green block crystals of (I) were obtained after cooling the solution to room temperature. The yield of (I) was ca 65%, based on 2, 2'-disulfanediyldibenzoic acid.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids drawn at the 35% probability level. Hydrogen atoms and are omitted for clarity.
	Fig. 2. View of the one-dimensional hydrogen-bonded chain of the title compound running along the a axis.

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

Crystal data top

[Ni₂(C₁₄H₈O₄S₂)₂(C₁₀H₈N₂)₂(H₂O)₂]	F(000) = 1104
M_r = 1074.47	D_x = 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

Data collection top

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

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)] = 0.029	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(F_o²) + (0.0369P)² + 0.5543P] where P = (F_o² + 2F_c²)/3
5302 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.34 e Å⁻³
3 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni₂(C₁₄H₈O₄S₂)₂(C₁₀H₈N₂)₂(H₂O)₂]	V = 2313.7 (12) Å³
M_r = 1074.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.498 (4) Å	µ = 1.06 mm⁻¹
b = 16.769 (5) Å	T = 296 K
c = 10.238 (3) Å	0.35 × 0.33 × 0.28 mm
β = 93.196 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	5302 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4428 reflections with I > 2σ(I)
T_min = 0.708, T_max = 0.756	R_int = 0.034
19861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	3 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.34 e Å⁻³
5302 reflections	Δρ_min = −0.26 e Å⁻³
307 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₄H₈O₄S₂)₂(C₁₀H₈N₂)₂(H₂O)₂]
M_r	1074.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.498 (4), 16.769 (5), 10.238 (3)
β (°)	93.196 (4)
V (Å³)	2313.7 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.35 × 0.33 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.708, 0.756
No. of measured, independent and observed [I > 2σ(I)] reflections	19861, 5302, 4428
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.06
No. of reflections	5302
No. of parameters	307
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O2	0.850 (9)	1.824 (11)	2.646 (2)	162 (2)
O5—H5A···O4ⁱ	0.841 (9)	1.888 (11)	2.7187 (18)	169 (2)

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by the Foundation of the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province.

References

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