Poly[[[μ-1,1'-(butane-1,4-di-yl)diimidazole-κN:N](μ-cyclo-hexane-1,4-dicarboxyl-ato-κO,O:O,O)nickel(II)] 0.25-hydrate].

In the title coordination polymer, {[Ni(C(8)H(10)O(4))(C(10)H(14)N(4))]·0.25H(2)O}(n), the coordination of the Ni(II) ion is distorted octa-hedral. The 1,1'-(butane-1,4-di-yl)diimidazole ligand and the cyclo-hexane-1,4-dicarboxyl-ate dianion bridge metal centres, forming a two-dimensional (4,4) network. The network is consolidated by O-H⋯O hydrogen bonds between the statistically occupied water molecules and O atoms of the two carboxylate groups.

Related literature

For potential applications of metal-organic coordination polymers, see: Yang et al. (2008 ▶). For metal-organic networks with diimidazole-containing ligands, see: Batten & Robson (1998 ▶). For flexible ligands such as 1,1′-(butane-1,4-di­yl)diimidazole, see: Ma et al. (2003 ▶).

Experimental

Crystal data

[Ni(C8H10O4)(C10H14N4)]·0.25H2O

M = 423.63

Monoclinic,

a = 9.0045 (9) Å

b = 11.9991 (12) Å

c = 17.5811 (17) Å

β = 95.755 (2)°

V = 1890.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.06 mm−1

T = 293 (2) K

0.31 × 0.27 × 0.22 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SAINT; Bruker, 1998 ▶) T min = 0.711, T max = 0.793

10421 measured reflections

3725 independent reflections

2999 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.03

3725 reflections

259 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004024/bt2863sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004024/bt2863Isup2.hkl

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

[Ni(C8H10O4)(C10H14N4)]·0.25H2O	F(000) = 890
Mr = 423.63	Dx = 1.489 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3725 reflections
a = 9.0045 (9) Å	θ = 1.1–26.0°
b = 11.9991 (12) Å	µ = 1.06 mm−1
c = 17.5811 (17) Å	T = 293 K
β = 95.755 (2)°	Block, green
V = 1890.0 (3) Å3	0.31 × 0.27 × 0.22 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	3725 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SAINT; Bruker, 1998)	h = −11→6
Tmin = 0.711, Tmax = 0.793	k = −14→14
10421 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3
3725 reflections	(Δ/σ)max = 0.002
259 parameters	Δρmax = 0.57 e Å−3
5 restraints	Δρmin = −0.27 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	Occ. (<1)
C1	0.4322 (3)	0.2316 (2)	0.81343 (15)	0.0268 (6)
H1	0.4040	0.2702	0.7684	0.032*
C2	0.5387 (3)	0.1159 (2)	0.89461 (16)	0.0324 (7)
H2	0.5993	0.0591	0.9162	0.039*
C3	0.4442 (3)	0.1774 (2)	0.93221 (16)	0.0348 (7)
H3	0.4277	0.1707	0.9834	0.042*
C4	0.2636 (3)	0.3356 (2)	0.89436 (17)	0.0299 (6)
H4A	0.2869	0.4051	0.8700	0.036*
H4B	0.2666	0.3491	0.9489	0.036*
C5	0.1088 (3)	0.2991 (2)	0.86426 (15)	0.0266 (6)
H5A	0.0832	0.2318	0.8906	0.032*
H5B	0.1070	0.2818	0.8103	0.032*
C6	−0.0072 (3)	0.3893 (2)	0.87522 (16)	0.0259 (6)
H6A	0.0055	0.4157	0.9276	0.031*
H6B	0.0076	0.4518	0.8418	0.031*
C7	−0.1640 (3)	0.3435 (2)	0.85724 (15)	0.0260 (6)
H7A	−0.1745	0.3144	0.8055	0.031*
H7B	−0.1788	0.2823	0.8917	0.031*
C8	−0.3756 (3)	0.4666 (2)	0.80760 (15)	0.0257 (6)
H8	−0.3762	0.4445	0.7569	0.031*
C9	−0.4306 (3)	0.5472 (2)	0.90939 (16)	0.0307 (6)
H9	−0.4775	0.5923	0.9427	0.037*
C10	−0.3131 (3)	0.4788 (2)	0.92988 (16)	0.0315 (7)
H10	−0.2652	0.4686	0.9788	0.038*
C11	0.8358 (3)	−0.0059 (2)	0.81662 (15)	0.0281 (6)
C12	0.9464 (3)	−0.0679 (2)	0.87253 (16)	0.0322 (7)
H12	0.9330	−0.0388	0.9235	0.039*
C13	1.1072 (3)	−0.0430 (2)	0.85861 (17)	0.0341 (7)
H13A	1.1218	0.0371	0.8576	0.041*
H13B	1.1264	−0.0724	0.8092	0.041*
C14	1.2175 (4)	−0.0939 (2)	0.92035 (17)	0.0426 (8)
H14A	1.2078	−0.0566	0.9685	0.051*
H14B	1.3183	−0.0815	0.9072	0.051*
C15	1.1929 (3)	−0.2187 (2)	0.93014 (16)	0.0365 (7)
H15	1.2505	−0.2404	0.9781	0.044*
C16	1.2504 (3)	−0.2892 (2)	0.86740 (15)	0.0270 (6)
C17	1.0291 (4)	−0.2452 (3)	0.93920 (17)	0.0432 (8)
H17A	1.0155	−0.3254	0.9388	0.052*
H17B	1.0048	−0.2175	0.9883	0.052*
C18	0.9220 (3)	−0.1936 (2)	0.87602 (17)	0.0370 (7)
H18A	0.8199	−0.2088	0.8858	0.044*
H18B	0.9385	−0.2269	0.8273	0.044*
N1	0.5319 (2)	0.14977 (17)	0.81948 (12)	0.0241 (5)
N2	0.3770 (2)	0.25174 (17)	0.88028 (12)	0.0260 (5)
N3	−0.2796 (2)	0.42811 (17)	0.86446 (12)	0.0233 (5)
N4	−0.4696 (2)	0.53970 (17)	0.83217 (12)	0.0243 (5)
O1	0.8555 (2)	0.09615 (14)	0.80581 (12)	0.0330 (5)
O2	0.7224 (2)	−0.05498 (15)	0.78388 (10)	0.0297 (4)
O1W	1.5782 (13)	−0.1622 (11)	0.8909 (6)	0.076 (3)	0.25
HW12	1.597 (7)	−0.104 (6)	0.865 (8)	0.115*	0.25
HW11	1.521 (4)	−0.200 (10)	0.858 (6)	0.115*	0.25
O3	1.3285 (2)	−0.24602 (14)	0.81902 (10)	0.0283 (4)
O4	1.2237 (2)	−0.39253 (14)	0.86564 (11)	0.0328 (5)
Ni1	0.65187 (3)	0.09925 (3)	0.733512 (18)	0.02147 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0233 (14)	0.0298 (14)	0.0270 (15)	0.0035 (11)	0.0003 (12)	0.0035 (12)
C2	0.0332 (16)	0.0337 (15)	0.0296 (15)	0.0115 (12)	−0.0007 (13)	0.0045 (12)
C3	0.0381 (17)	0.0397 (16)	0.0266 (15)	0.0086 (14)	0.0025 (13)	0.0046 (13)
C4	0.0230 (14)	0.0305 (14)	0.0365 (16)	0.0039 (12)	0.0046 (12)	−0.0050 (12)
C5	0.0243 (14)	0.0287 (14)	0.0272 (15)	0.0011 (11)	0.0048 (12)	−0.0024 (11)
C6	0.0224 (14)	0.0244 (13)	0.0313 (15)	0.0024 (11)	0.0041 (12)	−0.0001 (11)
C7	0.0242 (14)	0.0230 (13)	0.0303 (15)	0.0043 (11)	0.0007 (12)	−0.0027 (11)
C8	0.0243 (14)	0.0284 (14)	0.0241 (14)	0.0022 (11)	0.0009 (12)	−0.0028 (11)
C9	0.0273 (15)	0.0346 (15)	0.0302 (15)	0.0081 (12)	0.0032 (12)	−0.0073 (12)
C10	0.0290 (16)	0.0365 (15)	0.0280 (15)	0.0064 (12)	−0.0017 (12)	−0.0077 (12)
C11	0.0257 (15)	0.0274 (14)	0.0318 (16)	0.0069 (12)	0.0060 (12)	−0.0040 (12)
C12	0.0320 (16)	0.0341 (15)	0.0299 (15)	0.0124 (12)	0.0005 (13)	−0.0042 (12)
C13	0.0291 (16)	0.0247 (14)	0.0464 (18)	0.0060 (12)	−0.0067 (14)	−0.0076 (13)
C14	0.0414 (18)	0.0394 (17)	0.0433 (19)	0.0163 (14)	−0.0137 (15)	−0.0166 (14)
C15	0.0401 (18)	0.0447 (17)	0.0231 (15)	0.0223 (14)	−0.0046 (13)	−0.0018 (13)
C16	0.0215 (14)	0.0299 (14)	0.0277 (15)	0.0083 (11)	−0.0064 (12)	0.0022 (12)
C17	0.050 (2)	0.0512 (19)	0.0307 (17)	0.0219 (16)	0.0155 (15)	0.0141 (14)
C18	0.0321 (17)	0.0372 (16)	0.0432 (18)	0.0090 (13)	0.0115 (14)	0.0138 (14)
N1	0.0179 (11)	0.0246 (11)	0.0298 (13)	0.0026 (9)	0.0018 (10)	0.0000 (9)
N2	0.0202 (11)	0.0275 (11)	0.0305 (13)	0.0030 (9)	0.0034 (10)	−0.0006 (10)
N3	0.0197 (11)	0.0241 (11)	0.0260 (12)	0.0033 (9)	0.0013 (9)	−0.0034 (9)
N4	0.0189 (11)	0.0251 (11)	0.0292 (12)	0.0018 (9)	0.0034 (9)	−0.0022 (9)
O1	0.0229 (10)	0.0256 (10)	0.0488 (13)	0.0049 (8)	−0.0052 (9)	−0.0014 (9)
O2	0.0280 (10)	0.0236 (9)	0.0366 (11)	0.0021 (8)	−0.0016 (9)	−0.0010 (8)
O1W	0.087 (8)	0.089 (9)	0.053 (7)	−0.006 (7)	−0.001 (6)	0.003 (6)
O3	0.0332 (11)	0.0220 (9)	0.0298 (10)	0.0014 (8)	0.0041 (9)	0.0013 (8)
O4	0.0275 (11)	0.0276 (10)	0.0448 (12)	0.0037 (8)	0.0100 (9)	0.0034 (9)
Ni1	0.01688 (19)	0.01940 (18)	0.0281 (2)	−0.00028 (13)	0.00193 (14)	−0.00012 (14)

C1—N1	1.327 (3)	C12—C13	1.522 (4)
C1—N2	1.343 (3)	C12—C18	1.527 (4)
C1—H1	0.9300	C12—H12	0.9800
C2—C3	1.348 (4)	C13—C14	1.524 (4)
C2—N1	1.378 (3)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—N2	1.373 (3)	C14—C15	1.527 (4)
C3—H3	0.9300	C14—H14A	0.9700
C4—N2	1.472 (3)	C14—H14B	0.9700
C4—C5	1.506 (4)	C15—C16	1.521 (4)
C4—H4A	0.9700	C15—C17	1.533 (4)
C4—H4B	0.9700	C15—H15	0.9800
C5—C6	1.529 (3)	C16—O4	1.262 (3)
C5—H5A	0.9700	C16—O3	1.268 (3)
C5—H5B	0.9700	C16—Ni1i	2.455 (3)
C6—C7	1.519 (3)	C17—C18	1.527 (4)
C6—H6A	0.9700	C17—H17A	0.9700
C6—H6B	0.9700	C17—H17B	0.9700
C7—N3	1.469 (3)	C18—H18A	0.9700
C7—H7A	0.9700	C18—H18B	0.9700
C7—H7B	0.9700	N1—Ni1	2.036 (2)
C8—N4	1.322 (3)	N4—Ni1ii	2.039 (2)
C8—N3	1.336 (3)	O1—Ni1	2.1237 (18)
C8—H8	0.9300	O2—Ni1	2.1213 (18)
C9—C10	1.359 (4)	O1W—HW12	0.87 (2)
C9—N4	1.371 (3)	O1W—HW11	0.87 (2)
C9—H9	0.9300	O3—Ni1i	2.0890 (17)
C10—N3	1.361 (3)	O4—Ni1i	2.1668 (19)
C10—H10	0.9300	Ni1—N4iii	2.039 (2)
C11—O1	1.254 (3)	Ni1—O3iv	2.0890 (17)
C11—O2	1.266 (3)	Ni1—O4iv	2.1668 (19)
C11—C12	1.522 (4)	Ni1—C16iv	2.455 (3)
C11—Ni1	2.446 (3)
N1—C1—N2	111.7 (2)	C14—C15—C17	111.5 (2)
N1—C1—H1	124.1	C16—C15—H15	106.7
N2—C1—H1	124.1	C14—C15—H15	106.7
C3—C2—N1	109.8 (2)	C17—C15—H15	106.7
C3—C2—H2	125.1	O4—C16—O3	120.2 (2)
N1—C2—H2	125.1	O4—C16—C15	119.1 (3)
C2—C3—N2	106.7 (2)	O3—C16—C15	120.7 (2)
C2—C3—H3	126.7	O4—C16—Ni1i	61.85 (14)
N2—C3—H3	126.7	O3—C16—Ni1i	58.32 (13)
N2—C4—C5	112.0 (2)	C15—C16—Ni1i	178.8 (2)
N2—C4—H4A	109.2	C18—C17—C15	112.6 (2)
C5—C4—H4A	109.2	C18—C17—H17A	109.1
N2—C4—H4B	109.2	C15—C17—H17A	109.1
C5—C4—H4B	109.2	C18—C17—H17B	109.1
H4A—C4—H4B	107.9	C15—C17—H17B	109.1
C4—C5—C6	111.7 (2)	H17A—C17—H17B	107.8
C4—C5—H5A	109.3	C17—C18—C12	110.3 (3)
C6—C5—H5A	109.3	C17—C18—H18A	109.6
C4—C5—H5B	109.3	C12—C18—H18A	109.6
C6—C5—H5B	109.3	C17—C18—H18B	109.6
H5A—C5—H5B	107.9	C12—C18—H18B	109.6
C7—C6—C5	110.5 (2)	H18A—C18—H18B	108.1
C7—C6—H6A	109.5	C1—N1—C2	105.0 (2)
C5—C6—H6A	109.5	C1—N1—Ni1	124.44 (18)
C7—C6—H6B	109.5	C2—N1—Ni1	130.41 (18)
C5—C6—H6B	109.5	C1—N2—C3	106.7 (2)
H6A—C6—H6B	108.1	C1—N2—C4	126.5 (2)
N3—C7—C6	112.6 (2)	C3—N2—C4	126.8 (2)
N3—C7—H7A	109.1	C8—N3—C10	107.2 (2)
C6—C7—H7A	109.1	C8—N3—C7	125.8 (2)
N3—C7—H7B	109.1	C10—N3—C7	126.9 (2)
C6—C7—H7B	109.1	C8—N4—C9	105.0 (2)
H7A—C7—H7B	107.8	C8—N4—Ni1ii	123.59 (18)
N4—C8—N3	111.9 (2)	C9—N4—Ni1ii	130.52 (17)
N4—C8—H8	124.1	C11—O1—Ni1	88.94 (16)
N3—C8—H8	124.1	C11—O2—Ni1	88.73 (15)
C10—C9—N4	109.8 (2)	HW12—O1W—HW11	102 (3)
C10—C9—H9	125.1	C16—O3—Ni1i	90.59 (15)
N4—C9—H9	125.1	C16—O4—Ni1i	87.25 (16)
C9—C10—N3	106.2 (2)	N1—Ni1—N4iii	93.90 (8)
C9—C10—H10	126.9	N1—Ni1—O3iv	97.95 (8)
N3—C10—H10	126.9	N4iii—Ni1—O3iv	99.21 (8)
O1—C11—O2	120.3 (2)	N1—Ni1—O2	96.24 (8)
O1—C11—C12	118.8 (2)	N4iii—Ni1—O2	96.94 (8)
O2—C11—C12	120.8 (2)	O3iv—Ni1—O2	157.65 (7)
O1—C11—Ni1	60.23 (14)	N1—Ni1—O1	92.94 (8)
O2—C11—Ni1	60.11 (13)	N4iii—Ni1—O1	158.47 (7)
C12—C11—Ni1	176.46 (19)	O3iv—Ni1—O1	100.02 (7)
C11—C12—C13	111.8 (2)	O2—Ni1—O1	62.00 (7)
C11—C12—C18	114.9 (2)	N1—Ni1—O4iv	159.91 (8)
C13—C12—C18	110.1 (2)	N4iii—Ni1—O4iv	90.69 (8)
C11—C12—H12	106.5	O3iv—Ni1—O4iv	61.99 (7)
C13—C12—H12	106.5	O2—Ni1—O4iv	102.61 (7)
C18—C12—H12	106.5	O1—Ni1—O4iv	89.85 (8)
C12—C13—C14	111.7 (3)	N1—Ni1—C11	95.04 (8)
C12—C13—H13A	109.3	N4iii—Ni1—C11	128.02 (9)
C14—C13—H13A	109.3	O3iv—Ni1—C11	129.80 (8)
C12—C13—H13B	109.3	O2—Ni1—C11	31.17 (8)
C14—C13—H13B	109.3	O1—Ni1—C11	30.83 (8)
H13A—C13—H13B	107.9	O4iv—Ni1—C11	97.49 (8)
C13—C14—C15	112.5 (2)	N1—Ni1—C16iv	129.02 (9)
C13—C14—H14A	109.1	N4iii—Ni1—C16iv	96.21 (8)
C15—C14—H14A	109.1	O3iv—Ni1—C16iv	31.09 (8)
C13—C14—H14B	109.1	O2—Ni1—C16iv	131.55 (8)
C15—C14—H14B	109.1	O1—Ni1—C16iv	95.26 (8)
H14A—C14—H14B	107.8	O4iv—Ni1—C16iv	30.90 (8)
C16—C15—C14	113.6 (3)	C11—Ni1—C16iv	116.26 (9)
C16—C15—C17	111.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O2v	0.87 (2)	1.99 (5)	2.714 (11)	141 (7)
O1W—HW11···O3	0.87 (2)	1.88 (2)	2.663 (12)	149 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—HW12⋯O2i	0.87 (2)	1.99 (5)	2.714 (11)	141 (7)
O1W—HW11⋯O3	0.87 (2)	1.88 (2)	2.663 (12)	149 (4)

Symmetry code: (i) .