catena-Poly­[[di­aqua­bis(1H-benz­imidazole-κN³)­nickel(II)]-μ-fumarato-κ²O:O′]

The title compound, [Ni(μ-C₄H₂O₄)(C₇H₆N₂)₂(H₂O)₂]_n, is a one-dimensional polymeric complex bridged by fumarate dianions. The Ni atom lies on one inversion centre and the fumarate on another. The molecular chains are linked by hydrogen bonding. π–π stacking between parallel benz­imidazole rings exists in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.084
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

[Ni(C4H2O4)(C7H6N2)2(H2O)2]	Z = 1
Mr = 445.07	F(000) = 230
Triclinic, P1	Dx = 1.641 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.065 (1) Å	Cell parameters from 2668 reflections
b = 8.4842 (10) Å	θ = 3.0–26.0°
c = 8.6617 (9) Å	µ = 1.12 mm^−1
α = 98.471 (7)°	T = 295 K
β = 112.685 (4)°	Prism, green
γ = 103.098 (4)°	0.27 × 0.14 × 0.10 mm
V = 450.37 (10) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	1616 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 10.00 pixels mm^-1	θmax = 25.2°, θmin = 2.6°
ω scans	h = −8→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.74, Tmax = 0.89	l = −10→10
3114 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.3701P] where P = (Fo^2 + 2Fc^2)/3
1616 reflections	(Δ/σ)max = 0.001
139 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.5000	0.5000	0.5000	0.01881 (15)
O1	0.2747 (3)	0.26834 (19)	0.4323 (2)	0.0241 (4)
O2	0.1056 (3)	0.3179 (2)	0.5970 (2)	0.0270 (4)
O3	0.3007 (3)	0.6170 (2)	0.5673 (2)	0.0287 (4)
N1	0.7654 (4)	0.5579 (3)	1.0396 (3)	0.0305 (5)
H1	0.8118	0.6199	1.1427	0.037*
N3	0.6318 (3)	0.4840 (2)	0.7531 (2)	0.0248 (4)
C2	0.6916 (4)	0.6049 (3)	0.8925 (3)	0.0290 (5)
H2	0.6834	0.7123	0.8889	0.035*
C4	0.6353 (4)	0.1839 (3)	0.7276 (3)	0.0316 (6)
H4	0.5788	0.1519	0.6074	0.038*
C5	0.6882 (5)	0.0718 (4)	0.8249 (4)	0.0404 (7)
H5	0.6671	−0.0376	0.7694	0.049*
C6	0.7730 (6)	0.1205 (4)	1.0056 (4)	0.0478 (8)
H6	0.8065	0.0423	1.0678	0.057*
C7	0.8080 (5)	0.2797 (4)	1.0934 (4)	0.0411 (7)
H7	0.8660	0.3115	1.2137	0.049*
C8	0.7536 (4)	0.3922 (3)	0.9957 (3)	0.0276 (5)
C9	0.6692 (4)	0.3454 (3)	0.8153 (3)	0.0230 (5)
C11	0.1524 (4)	0.2216 (3)	0.5016 (3)	0.0220 (5)
C12	0.0593 (4)	0.0364 (3)	0.4650 (3)	0.0266 (5)
H12	0.0871	−0.0319	0.3874	0.032*
H3A	0.205 (7)	0.653 (6)	0.500 (6)	0.080*
H3B	0.216 (7)	0.534 (6)	0.581 (6)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0220 (2)	0.0152 (2)	0.0197 (2)	0.00365 (16)	0.01040 (17)	0.00524 (16)
O1	0.0284 (9)	0.0193 (8)	0.0249 (8)	0.0023 (7)	0.0148 (7)	0.0057 (6)
O2	0.0326 (9)	0.0212 (8)	0.0309 (9)	0.0066 (7)	0.0186 (8)	0.0061 (7)
O3	0.0313 (9)	0.0258 (9)	0.0344 (10)	0.0098 (7)	0.0185 (8)	0.0102 (8)
N1	0.0382 (12)	0.0326 (12)	0.0184 (10)	0.0113 (9)	0.0117 (9)	0.0016 (8)
N3	0.0298 (11)	0.0200 (10)	0.0235 (10)	0.0054 (8)	0.0115 (9)	0.0058 (8)
C2	0.0341 (13)	0.0237 (12)	0.0273 (12)	0.0073 (10)	0.0126 (11)	0.0055 (10)
C4	0.0413 (15)	0.0279 (13)	0.0276 (13)	0.0133 (11)	0.0155 (12)	0.0078 (11)
C5	0.0583 (18)	0.0312 (14)	0.0402 (15)	0.0213 (13)	0.0241 (14)	0.0141 (12)
C6	0.075 (2)	0.0460 (17)	0.0444 (17)	0.0369 (16)	0.0320 (16)	0.0284 (14)
C7	0.0569 (18)	0.0530 (18)	0.0246 (13)	0.0306 (15)	0.0189 (13)	0.0175 (13)
C8	0.0312 (12)	0.0311 (13)	0.0246 (12)	0.0129 (10)	0.0142 (10)	0.0083 (10)
C9	0.0245 (12)	0.0251 (12)	0.0228 (11)	0.0085 (9)	0.0120 (9)	0.0100 (9)
C11	0.0227 (11)	0.0200 (11)	0.0196 (11)	0.0038 (9)	0.0070 (9)	0.0053 (9)
C12	0.0311 (13)	0.0201 (12)	0.0311 (13)	0.0045 (10)	0.0185 (11)	0.0053 (10)

Geometric parameters (Å, º)

Ni—O1	2.0646 (15)	C4—C5	1.382 (4)
Ni—O3	2.0984 (18)	C4—C9	1.384 (4)
Ni—N3	2.0647 (19)	C4—H4	0.9300
O1—C11	1.257 (3)	C5—C6	1.398 (4)
O2—C11	1.263 (3)	C5—H5	0.9300
O3—H3A	0.85 (5)	C6—C7	1.366 (4)
O3—H3B	0.87 (5)	C6—H6	0.9300
N1—C2	1.336 (3)	C7—C8	1.388 (4)
N1—C8	1.376 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.395 (3)
N3—C2	1.316 (3)	C11—C12	1.492 (3)
N3—C9	1.401 (3)	C12—C12^i	1.310 (5)
C2—H2	0.9300	C12—H12	0.9300
O1—Ni—N3	89.40 (7)	C4—C5—H5	119.6
O1—Ni—O3	90.36 (7)	C6—C5—H5	119.6
N3—Ni—O3	86.66 (8)	C7—C6—C5	121.8 (3)
C11—O1—Ni	127.73 (15)	C7—C6—H6	119.1
Ni—O3—H3A	126 (3)	C5—C6—H6	119.1
Ni—O3—H3B	101 (3)	C6—C7—C8	117.3 (3)
H3A—O3—H3B	99 (4)	C6—C7—H7	121.3
C2—N1—C8	107.4 (2)	C8—C7—H7	121.3
C2—N1—H1	126.3	N1—C8—C7	132.8 (2)
C8—N1—H1	126.3	N1—C8—C9	105.8 (2)
C2—N3—C9	104.98 (19)	C7—C8—C9	121.4 (2)
C2—N3—Ni	126.05 (17)	C4—C9—C8	120.8 (2)
C9—N3—Ni	128.93 (16)	C4—C9—N3	130.6 (2)
N3—C2—N1	113.2 (2)	C8—C9—N3	108.6 (2)
N3—C2—H2	123.4	O1—C11—O2	125.2 (2)
N1—C2—H2	123.4	O1—C11—C12	115.3 (2)
C5—C4—C9	117.7 (2)	O2—C11—C12	119.4 (2)
C5—C4—H4	121.1	C12^i—C12—C11	124.3 (3)
C9—C4—H4	121.1	C12^i—C12—H12	117.8
C4—C5—C6	120.9 (3)	C11—C12—H12	117.8

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	0.86	2.05	2.868 (3)	159
O3—H3A···O2^iii	0.86 (5)	2.11 (5)	2.893 (3)	151 (5)
O3—H3B···O2	0.87 (5)	1.87 (5)	2.699 (3)	159 (5)

Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+1.