Poly[diaqua-[μ-1,4-bis-(1H-imidazol-1-yl)benzene-κ(2)N(3):N(3')](μ-fumarato-κ(2)O(1):O(4))nickel(II)].

In the title compound, [Ni(C(4)H(2)O(4))(C(12)H(10)N(4))(H(2)O)(2)](n), the Ni(II) ion has a distorted octa-hedral coordination geometry. The asymmetric unit is composed of an Ni(2+) ion, located on a twofold rotation axis, one half of a 1,4-bis-(1H-imidazol-1-yl)benzene (BIMB) ligand and one half of a fumarte (fum(2-)) dianion, both ligands being located about inversion centers, and a coordinating water mol-ecule. The Ni(II) ions are linked by two BIMB ligands and two fum(2-) dianions, forming a four-connected layered structure parallel to (010) with a 4(4)-sql topology. Within each layer, there are rhombic grids with dimensions of ca 13.5 × 9.0 Å and approximate angles of 109 and 70°. The crystal packing features a two-dimensional → two-dimensional parallel/parallel interpenetration in which one undulating layer is catenated to another equivalent one, forming a new bilayer. Moreover, the entangled two-dimensional layers are connected by O-H⋯O and C-H⋯O hydrogen bonds, generating a three-dimensional structure.

Related literature

For multi-dimensional coordination polymers and their applications, see: Batten & Robson (1998 ▶); Carlucci et al. (2003a ▶,b ▶); Moulton & Zaworotko (2001 ▶); Sun et al. (2006 ▶); Wu et al. (2011 ▶); Bu et al. (2004 ▶). For their potential applications in electron transfer and drug delivery, see: Harriman & Sauvage (1996 ▶); Raymo & Sauvage (1999 ▶). For the structures of some related compounds, see: Chen et al. (2010 ▶); Li et al. (2012 ▶); Bu et al. (2004 ▶).

Experimental

Crystal data

[Ni(C4H2O4)(C12H10N4)(H2O)2]

M = 419.04

Orthorhombic,

a = 11.2806 (4) Å

b = 16.3703 (7) Å

c = 9.0253 (3) Å

V = 1666.67 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.21 mm−1

T = 296 K

0.23 × 0.22 × 0.20 mm

Data collection

Bruke APEXII CCD area-dector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.768, T max = 0.794

8512 measured reflections

2108 independent reflections

1827 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.093

S = 1.08

2108 reflections

123 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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 (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038895/su2481sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038895/su2481Isup2.hkl

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

[Ni(C4H2O4)(C12H10N4)(H2O)2]	F(000) = 864
Mr = 419.04	Dx = 1.670 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4217 reflections
a = 11.2806 (4) Å	θ = 2.5–28.4°
b = 16.3703 (7) Å	µ = 1.21 mm−1
c = 9.0253 (3) Å	T = 296 K
V = 1666.67 (11) Å3	Block, green
Z = 4	0.23 × 0.22 × 0.20 mm

Bruke APEXII CCD area-dector diffractometer	2108 independent reflections
Radiation source: fine-focus sealed tube	1827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
CCD rotation images, thin slices scans	θmax = 28.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
Tmin = 0.768, Tmax = 0.794	k = −18→21
8512 measured reflections	l = −12→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.047P)2 + 1.0911P] where P = (Fo2 + 2Fc2)/3
2108 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.36 e Å−3
2 restraints	Δρmin = −0.48 e Å−3

Experimental. Spectroscopic data for the title compound :IR (KBr, cm-1): 3380m, 3133m, 1564s, 1533s, 1385s, 1307w, 1269w, 1130w, 1195w, 1074m, 970w, 880w, 829m, 751m, 682w, 656w, 534w, 495w.

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
C1	0.85967 (16)	0.48653 (12)	0.8087 (2)	0.0337 (4)
H1	0.9127	0.5069	0.8785	0.040*
C2	0.76108 (18)	0.52549 (13)	0.7609 (2)	0.0353 (4)
H2	0.7344	0.5768	0.7899	0.042*
C3	0.77741 (16)	0.40688 (11)	0.6505 (2)	0.0294 (4)
H3	0.7616	0.3627	0.5889	0.035*
C4	0.57558 (18)	0.56487 (12)	0.5293 (3)	0.0409 (5)
H4	0.6266	0.6082	0.5487	0.049*
C5	0.60153 (15)	0.48748 (11)	0.5802 (2)	0.0290 (4)
C6	0.52718 (19)	0.42289 (12)	0.5509 (3)	0.0408 (5)
H6	0.5461	0.3709	0.5851	0.049*
C7	1.08521 (15)	0.29993 (11)	0.43626 (19)	0.0266 (3)
C8	1.05530 (18)	0.30159 (14)	0.2748 (2)	0.0348 (4)
H8	1.1169	0.3027	0.2064	0.042*
N1	0.86960 (13)	0.41195 (10)	0.73829 (16)	0.0261 (3)
N2	0.70833 (13)	0.47384 (9)	0.66080 (18)	0.0288 (3)
Ni1	1.0000	0.323481 (18)	0.7500	0.01981 (12)
O1	1.00329 (10)	0.31848 (9)	0.52371 (16)	0.0310 (3)
O2	1.18776 (11)	0.27709 (9)	0.47076 (14)	0.0347 (3)
O3	0.86671 (12)	0.23178 (8)	0.74938 (13)	0.0291 (3)
H3Y	0.8214	0.2383	0.8237	0.044*
H3X	0.8264	0.2356	0.6701	0.044*

	U11	U22	U33	U12	U13	U23
C1	0.0277 (8)	0.0378 (10)	0.0358 (10)	0.0029 (7)	−0.0078 (8)	−0.0101 (8)
C2	0.0317 (9)	0.0328 (9)	0.0414 (11)	0.0050 (8)	−0.0073 (8)	−0.0121 (8)
C3	0.0260 (8)	0.0294 (9)	0.0327 (9)	0.0065 (7)	−0.0078 (7)	−0.0043 (7)
C4	0.0341 (10)	0.0268 (9)	0.0617 (14)	0.0004 (7)	−0.0200 (10)	−0.0014 (9)
C5	0.0221 (8)	0.0304 (9)	0.0344 (9)	0.0059 (6)	−0.0081 (7)	−0.0022 (7)
C6	0.0358 (10)	0.0244 (8)	0.0621 (14)	0.0050 (7)	−0.0197 (10)	0.0031 (9)
C7	0.0272 (8)	0.0337 (9)	0.0189 (7)	0.0008 (7)	−0.0008 (6)	−0.0015 (7)
C8	0.0321 (10)	0.0489 (11)	0.0233 (8)	0.0010 (9)	0.0014 (7)	0.0001 (8)
N1	0.0212 (7)	0.0307 (8)	0.0266 (7)	0.0027 (6)	−0.0046 (5)	−0.0025 (6)
N2	0.0230 (7)	0.0287 (7)	0.0346 (8)	0.0049 (6)	−0.0086 (6)	−0.0031 (6)
Ni1	0.01593 (17)	0.02772 (18)	0.01579 (17)	0.000	−0.00177 (9)	0.000
O1	0.0255 (6)	0.0512 (9)	0.0164 (6)	0.0054 (5)	−0.0009 (4)	−0.0025 (5)
O2	0.0270 (6)	0.0532 (8)	0.0238 (6)	0.0093 (6)	0.0004 (5)	−0.0013 (6)
O3	0.0263 (6)	0.0357 (7)	0.0253 (7)	−0.0042 (5)	−0.0021 (5)	−0.0035 (5)

C1—C2	1.353 (3)	C6—H6	0.9300
C1—N1	1.381 (2)	C7—O1	1.253 (2)
C1—H1	0.9300	C7—O2	1.255 (2)
C2—N2	1.373 (2)	C7—C8	1.496 (3)
C2—H2	0.9300	C8—C8ii	1.326 (4)
C3—N1	1.310 (2)	C8—H8	0.9300
C3—N2	1.348 (2)	N1—Ni1	2.0670 (15)
C3—H3	0.9300	Ni1—O1	2.0443 (15)
C4—C5	1.379 (3)	Ni1—O1iii	2.0443 (15)
C4—C6i	1.381 (3)	Ni1—N1iii	2.0671 (15)
C4—H4	0.9300	Ni1—O3iii	2.1247 (13)
C5—C6	1.375 (3)	Ni1—O3	2.1247 (13)
C5—N2	1.425 (2)	O3—H3Y	0.8500
C6—C4i	1.381 (3)	O3—H3X	0.8501
C2—C1—N1	109.66 (16)	C3—N1—Ni1	123.47 (13)
C2—C1—H1	125.2	C1—N1—Ni1	130.81 (12)
N1—C1—H1	125.2	C3—N2—C2	107.19 (15)
C1—C2—N2	106.02 (17)	C3—N2—C5	125.53 (15)
C1—C2—H2	127.0	C2—N2—C5	127.28 (15)
N2—C2—H2	127.0	O1—Ni1—O1iii	175.41 (8)
N1—C3—N2	111.46 (16)	O1—Ni1—N1	89.42 (5)
N1—C3—H3	124.3	O1iii—Ni1—N1	93.80 (5)
N2—C3—H3	124.3	O1—Ni1—N1iii	93.79 (5)
C5—C4—C6i	119.07 (18)	O1iii—Ni1—N1iii	89.42 (5)
C5—C4—H4	120.5	N1—Ni1—N1iii	91.04 (9)
C6i—C4—H4	120.5	O1—Ni1—O3iii	87.80 (5)
C6—C5—C4	120.85 (16)	O1iii—Ni1—O3iii	88.96 (5)
C6—C5—N2	119.55 (16)	N1—Ni1—O3iii	177.19 (5)
C4—C5—N2	119.57 (16)	N1iii—Ni1—O3iii	89.51 (6)
C5—C6—C4i	120.07 (18)	O1—Ni1—O3	88.96 (5)
C5—C6—H6	120.0	O1iii—Ni1—O3	87.79 (5)
C4i—C6—H6	120.0	N1—Ni1—O3	89.50 (6)
O1—C7—O2	126.58 (16)	N1iii—Ni1—O3	177.19 (5)
O1—C7—C8	116.29 (16)	O3iii—Ni1—O3	90.09 (8)
O2—C7—C8	117.06 (16)	C7—O1—Ni1	130.74 (12)
C8ii—C8—C7	122.8 (2)	Ni1—O3—H3Y	109.6
C8ii—C8—H8	118.6	Ni1—O3—H3X	109.3
C7—C8—H8	118.6	H3Y—O3—H3X	109.5
C3—N1—C1	105.67 (15)
N1—C1—C2—N2	0.8 (2)	C4—C5—N2—C2	36.9 (3)
C6i—C4—C5—C6	0.6 (4)	C3—N1—Ni1—O1	45.30 (16)
C6i—C4—C5—N2	178.9 (2)	C1—N1—Ni1—O1	−131.70 (17)
C4—C5—C6—C4i	−0.6 (4)	C3—N1—Ni1—O1iii	−131.42 (15)
N2—C5—C6—C4i	−178.9 (2)	C1—N1—Ni1—O1iii	51.58 (17)
O1—C7—C8—C8ii	−16.9 (2)	C3—N1—Ni1—N1iii	139.09 (17)
O2—C7—C8—C8ii	160.34 (12)	C1—N1—Ni1—N1iii	−37.91 (15)
N2—C3—N1—C1	−0.2 (2)	C3—N1—Ni1—O3iii	38.0 (12)
N2—C3—N1—Ni1	−177.88 (12)	C1—N1—Ni1—O3iii	−139.0 (10)
C2—C1—N1—C3	−0.4 (2)	C3—N1—Ni1—O3	−43.66 (15)
C2—C1—N1—Ni1	177.04 (15)	C1—N1—Ni1—O3	139.33 (17)
N1—C3—N2—C2	0.7 (2)	O2—C7—O1—Ni1	2.1 (3)
N1—C3—N2—C5	−179.97 (17)	C8—C7—O1—Ni1	179.05 (13)
C1—C2—N2—C3	−0.9 (2)	O1iii—Ni1—O1—C7	−73.40 (17)
C1—C2—N2—C5	179.80 (19)	N1—Ni1—O1—C7	152.04 (17)
C6—C5—N2—C3	36.0 (3)	N1iii—Ni1—O1—C7	61.04 (17)
C4—C5—N2—C3	−142.3 (2)	O3iii—Ni1—O1—C7	−28.32 (17)
C6—C5—N2—C2	−144.8 (2)	O3—Ni1—O1—C7	−118.44 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3Y···O2iii	0.85	1.96	2.7033 (18)	146
O3—H3X···O2iv	0.85	2.03	2.8361 (18)	159
C3—H3···O2iv	0.93	2.49	3.360 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3Y⋯O2i	0.85	1.96	2.7033 (18)	146
O3—H3X⋯O2ii	0.85	2.03	2.8361 (18)	159
C3—H3⋯O2ii	0.93	2.49	3.360 (2)	155

Symmetry codes: (i) ; (ii) .