Poly[[[μ-1,1′-(butane-1,4-di­yl)diimidazole-κ2N3:N3′](μ-cyclo­hexane-1,4-dicarboxyl­ato-κ4O1,O1′:O4,O4′)nickel(II)] 0.25-hydrate]

Yang, C.-H.; Yang, G.; Du, Z.-W.; Lv, J.-F.; Yin, W.-T.

doi:10.1107/S1600536809004024

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m263

doi:10.1107/S1600536809004024

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Poly[[[μ-1,1′-(butane-1,4-diyl)diimidazole-κ²N³:N^3′](μ-cyclohexane-1,4-dicarboxylato-κ⁴O¹,O^1′:O⁴,O^4′)nickel(II)] 0.25-hydrate]

Chun-Hui Yang,^a Guang Yang,^a Zhen-Wu Du,^b Jun-Feng Lv ^c and Wei-Tian Yin ^a ^*

^aThe Third Hospital of Jilin University, Changchun 130000, People's Republic of China, ^bSchool of Pharmaceurtical Sciences, Jilin University, Changchun 130000, People's Republic of China, and ^cThe Second Hospital of Jilin University, Changchun 130000, People's Republic of China
^*Correspondence e-mail: weitianyin0431@yahoo.com.cn

(Received 31 January 2009; accepted 3 February 2009; online 11 February 2009)

In the title coordination polymer, {[Ni(C₈H₁₀O₄)(C₁₀H₁₄N₄)]·0.25H₂O}_n, the coordination of the Ni^II ion is distorted octahedral. The 1,1′-(butane-1,4-diyl)diimidazole ligand and the cyclohexane-1,4-dicarboxylate 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_r = 423.63
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.097
S = 1.03
3725 reflections
259 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) x+1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Metal-organic coordination polymers are currently of great interest due to their interesting structures and potential applications (Yang et al., 2008). So far, some interesting interpenetrated or entangled metal-organic networks with diimidazole-containing ligands have been documented (Batten & Robson, 1998). Flexible ligands such as 1,1'-(butane-1,4-diyl)diimidazole (L) have not been well explored to date (Ma et al., 2003). In this work, we selected cyclohexane-1,4-dicarboxylatic acid (H₂cdc) and L as linkers, generating a new coordination polymer, [Ni(cdc)(L)]^.0.25H₂O, (I), which is reported here.

In compound (I) each Ni^II atom is six-coordinated by two N atoms from two different L ligands, and four O atoms from two different cdc ligands in a distorted octohedral coordination sphere. The two neighbouring Ni^II atoms are bridged by the cdc and L ligands to form a two-dimensional (4,4) network. The O–H···O hydrogen bonds observed in the network consolidated the structure of (I) (Table 1).

Related literature top

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 top

A mixture of H₂cdc (0.5 mmol), L (0.5 mmol), NaOH (1 mmol) and NiCl₂^.6H₂O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 140°C for three days, the autoclave was slowly cooled to room temperature. The crystals were collected, washed with deionized water and dried.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot at the 30% probability level; hydrogen atoms are drawn as spheres of arbitrary radius; symmetry operations i: 2 - x, 1/2 + y, 1.5 - z; ii: -x, y - 1/2, 1.5 - z).
	Fig. 2. A view of the two-dimensional (4,4) network of (I).

Poly[[[µ-1,1'-(butane-1,4-diyl)diimidazole- κ²N³:N^3'](µ-cyclohexane-1,4-dicarboxylato- κ⁴O¹,O^1':O⁴,O^4')nickel(II)] 0.25-hydrate] top

Crystal data top

[Ni(C₈H₁₀O₄)(C₁₀H₁₄N₄)]·0.25H₂O	F(000) = 890
M_r = 423.63	D_x = 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

Data collection top

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

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)] = 0.040	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(F_o²) + (0.0493P)²] where P = (F_o² + 2F_c²)/3
3725 reflections	(Δ/σ)_max = 0.002
259 parameters	Δρ_max = 0.57 e Å⁻³
5 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Ni(C₈H₁₀O₄)(C₁₀H₁₄N₄)]·0.25H₂O	V = 1890.0 (3) Å³
M_r = 423.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0045 (9) Å	µ = 1.06 mm⁻¹
b = 11.9991 (12) Å	T = 293 K
c = 17.5811 (17) Å	0.31 × 0.27 × 0.22 mm
β = 95.755 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3725 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1998)	2999 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.793	R_int = 0.040
10421 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	5 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.57 e Å⁻³
3725 reflections	Δρ_min = −0.27 e Å⁻³
259 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O3^iv	2.0890 (17)
C11—O2	1.266 (3)	Ni1—O4^iv	2.1668 (19)
C11—C12	1.522 (4)	Ni1—C16^iv	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—O3^iv	97.95 (8)
N3—C10—H10	126.9	N4ⁱⁱⁱ—Ni1—O3^iv	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)	O3^iv—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)	O3^iv—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—O4^iv	159.91 (8)
C13—C12—C18	110.1 (2)	N4ⁱⁱⁱ—Ni1—O4^iv	90.69 (8)
C11—C12—H12	106.5	O3^iv—Ni1—O4^iv	61.99 (7)
C13—C12—H12	106.5	O2—Ni1—O4^iv	102.61 (7)
C18—C12—H12	106.5	O1—Ni1—O4^iv	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	O3^iv—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	O4^iv—Ni1—C11	97.49 (8)
C13—C14—C15	112.5 (2)	N1—Ni1—C16^iv	129.02 (9)
C13—C14—H14A	109.1	N4ⁱⁱⁱ—Ni1—C16^iv	96.21 (8)
C15—C14—H14A	109.1	O3^iv—Ni1—C16^iv	31.09 (8)
C13—C14—H14B	109.1	O2—Ni1—C16^iv	131.55 (8)
C15—C14—H14B	109.1	O1—Ni1—C16^iv	95.26 (8)
H14A—C14—H14B	107.8	O4^iv—Ni1—C16^iv	30.90 (8)
C16—C15—C14	113.6 (3)	C11—Ni1—C16^iv	116.26 (9)
C16—C15—C17	111.2 (3)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O2^v	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: (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₁₀O₄)(C₁₀H₁₄N₄)]·0.25H₂O
M_r	423.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.0045 (9), 11.9991 (12), 17.5811 (17)
β (°)	95.755 (2)
V (Å³)	1890.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.31 × 0.27 × 0.22

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SAINT; Bruker, 1998)
T_min, T_max	0.711, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	10421, 3725, 2999
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.03
No. of reflections	3725
No. of parameters	259
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.27

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Acknowledgements

We thank the Third Hospital of Jilin University for supporting this study.

References

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494. Web of Science CrossRef Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531–7534. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, J., Ma, J.-F., Batten, S. R. & Su, Z.-M. (2008). Chem. Commun. pp. 2233–2235. Web of Science CSD CrossRef Google Scholar

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