Poly[aqua­[μ2-1,1′-(butane-1,4-di­yl)diimidazole](μ2-naphthalene-1,4-dicarboxyl­ato)nickel(II)]

Zou, X.-Z.

doi:10.1107/S1600536808024008

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1105

doi:10.1107/S1600536808024008

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Poly[aqua[μ₂-1,1′-(butane-1,4-diyl)diimidazole](μ₂-naphthalene-1,4-dicarboxylato)nickel(II)]

Xian-Zhi Zou ^a ^*

^aDepartment of Chemistry, College of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jlsxzz@126.com

(Received 24 July 2008; accepted 29 July 2008; online 6 August 2008)

In the title compound, [Ni(C₁₂H₆O₄)(C₁₀H₁₄N₄)(H₂O)]_n, the coordination polyhedron around each Ni^II atom is a distorted cis-NiN₂O₄ octahedron. The naphthalene-1,4-dicarboxylate and 1,1′-(butane-1,4-diyl)diimidazole ligands bridge the Ni centres to form a two-dimensional (4,4)-network, and O—H⋯O hydrogen bonds complete the structure.

Related literature

For general background, see: Batten & Robson (1998 ). For a related structure, see: Ma et al., (2003 ).

Experimental

Crystal data

[Ni(C₁₂H₆O₄)(C₁₀H₁₄N₄)(H₂O)]
M_r = 481.15
Monoclinic, P 2₁ /n
a = 12.4213 (12) Å
b = 13.2543 (13) Å
c = 13.4328 (13) Å
β = 107.361 (2)°
V = 2110.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 293 (2) K
0.19 × 0.17 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.827, T_max = 0.866
11720 measured reflections
4157 independent reflections
2982 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.097
S = 1.05
4157 reflections
297 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1W	2.125 (2)
Ni1—O2	2.040 (2)
Ni1—O1ⁱ	2.116 (2)
Ni1—O3ⁱ	2.347 (2)
Ni1—N1	2.060 (3)
Ni1—N4ⁱⁱ	2.099 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—HW12⋯O1ⁱⁱⁱ	0.819 (16)	1.847 (18)	2.661 (3)	172 (3)
O1W—HW11⋯O4	0.83 (4)	1.83 (4)	2.651 (3)	169 (3)
Symmetry code: (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808024008/hb2770sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024008/hb2770Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks are currently of great interest because of their interesting structures and potential applications. So far, some interesting interpenetrated or entangled metal-organic networks with bis(imidazole)-containing ligands have been documented (Batten & Robson, 1998). Flexible ligands such as 1,1'-(1,4-butanediyl)bis(imidazole) (L) have been less explored to date (Ma et al., 2003). In this work, we selected 1,4-naphthalenedicarboxylic acid (H₂ndc) and L as linkers, generating a new coordination polymer, [Ni(ndc)(L)(H₂O)], (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 three carboxylate oxygen atoms (one bidentate, one monodentate) and one water molecule in a distorted cis-NiN₂O₄ octohedral coordination sphere (Fig. 1). The two neighbouring Ni^II atoms are bridged by the ndc and L ligands to form a two-dimensional (4,4) network (Fig. 2) and O—H···O hydrogen bonds arising from the water molecule (Table 2) complete the structure.

Related literature top

For general background, see: Batten & Robson (1998). For a related structure, see: Ma et al., (2003).

Experimental top

A mixture of H₂ndc (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 433 K for one week, the autoclave was slowly cooled to room temperature. Green blocks of (I) were collected, washed with deionized water and dried.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (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. The structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. Symmetry codes: (i) x, y - 1, z; (ii) 1/2 + x, 0.5 - y, z - 1/2.
	Fig. 2. View of part of the polymeric layer structure of (I).

Poly[aqua[µ₂-1,1'-(butane-1,4-diyl)diimidazole](µ₂-naphthalene-1,4- dicarboxylato)nickel(II)] top

Crystal data top

[Ni(C₁₂H₆O₄)(C₁₀H₁₄N₄)(H₂O)]	F(000) = 1000
M_r = 481.15	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4157 reflections
a = 12.4213 (12) Å	θ = 1.9–26.1°
b = 13.2543 (13) Å	µ = 0.96 mm⁻¹
c = 13.4328 (13) Å	T = 293 K
β = 107.361 (2)°	Block, green
V = 2110.8 (4) Å³	0.19 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 26.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→15
T_min = 0.827, T_max = 0.866	k = −16→14
11720 measured reflections	l = −16→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0253P)²] where P = (F_o² + 2F_c²)/3
4157 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.54 e Å⁻³
3 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Ni(C₁₂H₆O₄)(C₁₀H₁₄N₄)(H₂O)]	V = 2110.8 (4) Å³
M_r = 481.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4213 (12) Å	µ = 0.96 mm⁻¹
b = 13.2543 (13) Å	T = 293 K
c = 13.4328 (13) Å	0.19 × 0.17 × 0.15 mm
β = 107.361 (2)°

Data collection top

Bruker APEX CCD diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2982 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.866	R_int = 0.063
11720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.54 e Å⁻³
4157 reflections	Δρ_min = −0.40 e Å⁻³
297 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
C1	0.2969 (3)	0.1196 (2)	0.2222 (3)	0.0208 (8)
C2	0.2145 (3)	0.1584 (2)	0.2758 (2)	0.0190 (8)
C3	0.2114 (3)	0.2586 (2)	0.2946 (3)	0.0264 (9)
H3	0.2583	0.3019	0.2721	0.032*
C4	0.1392 (3)	0.2986 (2)	0.3472 (3)	0.0238 (8)
H4	0.1399	0.3677	0.3597	0.029*
C5	0.0674 (3)	0.2376 (2)	0.3805 (2)	0.0203 (8)
C6	−0.0034 (3)	0.2829 (2)	0.4420 (3)	0.0218 (8)
C7	0.0636 (3)	0.1328 (2)	0.3576 (2)	0.0180 (7)
C8	0.1382 (3)	0.0919 (2)	0.3055 (2)	0.0172 (7)
C9	0.1306 (3)	−0.0118 (2)	0.2806 (3)	0.0256 (8)
H9	0.1795	−0.0393	0.2473	0.031*
C10	0.0536 (3)	−0.0723 (3)	0.3042 (3)	0.0281 (9)
H10	0.0497	−0.1404	0.2868	0.034*
C11	−0.0196 (3)	−0.0320 (3)	0.3546 (3)	0.0312 (9)
H11	−0.0722	−0.0738	0.3706	0.037*
C12	−0.0157 (3)	0.0664 (2)	0.3806 (3)	0.0257 (8)
H12	−0.0657	0.0914	0.4141	0.031*
C13	0.1710 (3)	0.2460 (3)	−0.1581 (3)	0.0335 (10)
H13	0.1644	0.1937	−0.2056	0.040*
C14	0.1151 (4)	0.3340 (3)	−0.1787 (3)	0.0430 (11)
H14	0.0644	0.3537	−0.2418	0.052*
C15	0.2219 (3)	0.3312 (3)	−0.0198 (3)	0.0310 (9)
H15	0.2581	0.3510	0.0484	0.037*
C16	0.1118 (3)	0.4914 (2)	−0.0714 (3)	0.0274 (9)
H16A	0.1268	0.5024	0.0029	0.033*
H16B	0.0311	0.4976	−0.1039	0.033*
C17	0.1715 (3)	0.5711 (2)	−0.1149 (3)	0.0296 (9)
H17A	0.1498	0.5648	−0.1903	0.036*
H17B	0.2523	0.5605	−0.0882	0.036*
C18	0.1434 (3)	0.6771 (2)	−0.0863 (3)	0.0293 (9)
H18A	0.0622	0.6862	−0.1083	0.035*
H18B	0.1705	0.6855	−0.0112	0.035*
C19	0.1971 (3)	0.7560 (2)	−0.1379 (3)	0.0293 (9)
H19A	0.2754	0.7381	−0.1277	0.035*
H19B	0.1590	0.7559	−0.2123	0.035*
C20	0.1050 (3)	0.9021 (3)	−0.0704 (3)	0.0395 (11)
H20	0.0353	0.8734	−0.0749	0.047*
C21	0.2746 (3)	0.9270 (2)	−0.0777 (3)	0.0238 (8)
H21	0.3436	0.9163	−0.0898	0.029*
N4	0.2477 (2)	1.01080 (19)	−0.0399 (2)	0.0212 (7)
C23	0.1402 (3)	0.9948 (3)	−0.0365 (3)	0.0378 (10)
H23	0.0973	1.0419	−0.0137	0.045*
N1	0.2384 (2)	0.2446 (2)	−0.0581 (2)	0.0224 (7)
N2	0.1476 (2)	0.38862 (19)	−0.0887 (2)	0.0232 (7)
N3	0.1920 (2)	0.8579 (2)	−0.0970 (2)	0.0240 (7)
O1	−0.05860 (18)	0.36339 (16)	0.40707 (17)	0.0227 (5)
O2	0.3062 (2)	0.17401 (16)	0.14730 (18)	0.0266 (6)
O1W	0.4733 (2)	0.04150 (17)	0.12115 (19)	0.0208 (6)
O3	−0.00731 (19)	0.24467 (16)	0.52507 (17)	0.0265 (6)
O4	0.35191 (19)	0.04171 (16)	0.25344 (18)	0.0257 (6)
Ni1	0.35134 (4)	0.13565 (3)	0.01819 (3)	0.02231 (14)
HW12	0.495 (2)	−0.0135 (16)	0.107 (2)	0.020 (10)*
HW11	0.440 (3)	0.034 (2)	0.166 (2)	0.053 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (2)	0.0180 (19)	0.0236 (19)	−0.0040 (15)	0.0094 (15)	−0.0067 (15)
C2	0.025 (2)	0.0174 (19)	0.0172 (18)	0.0032 (14)	0.0099 (15)	0.0011 (14)
C3	0.034 (2)	0.0166 (19)	0.037 (2)	−0.0033 (16)	0.0226 (18)	0.0027 (16)
C4	0.033 (2)	0.0108 (18)	0.033 (2)	0.0005 (15)	0.0184 (18)	−0.0043 (15)
C5	0.024 (2)	0.0201 (19)	0.0198 (19)	0.0018 (15)	0.0110 (15)	0.0017 (15)
C6	0.023 (2)	0.0178 (19)	0.028 (2)	−0.0063 (15)	0.0133 (17)	−0.0083 (16)
C7	0.0207 (18)	0.0162 (18)	0.0187 (17)	0.0009 (14)	0.0085 (14)	0.0007 (14)
C8	0.0238 (19)	0.0136 (17)	0.0162 (17)	0.0012 (14)	0.0088 (15)	0.0009 (13)
C9	0.030 (2)	0.021 (2)	0.030 (2)	0.0018 (16)	0.0157 (17)	−0.0013 (16)
C10	0.034 (2)	0.0147 (19)	0.039 (2)	−0.0018 (16)	0.0167 (19)	−0.0041 (16)
C11	0.037 (2)	0.022 (2)	0.041 (2)	−0.0094 (17)	0.021 (2)	−0.0018 (17)
C12	0.030 (2)	0.025 (2)	0.028 (2)	−0.0024 (16)	0.0182 (17)	−0.0027 (16)
C13	0.047 (3)	0.023 (2)	0.029 (2)	0.0090 (18)	0.0076 (19)	−0.0050 (17)
C14	0.057 (3)	0.035 (2)	0.026 (2)	0.019 (2)	−0.004 (2)	0.0003 (18)
C15	0.035 (2)	0.024 (2)	0.027 (2)	0.0056 (17)	−0.0011 (18)	−0.0046 (16)
C16	0.027 (2)	0.019 (2)	0.037 (2)	0.0056 (15)	0.0124 (18)	−0.0005 (16)
C17	0.030 (2)	0.020 (2)	0.039 (2)	0.0018 (16)	0.0105 (18)	−0.0001 (17)
C18	0.029 (2)	0.020 (2)	0.039 (2)	0.0005 (16)	0.0105 (18)	0.0004 (17)
C19	0.033 (2)	0.020 (2)	0.036 (2)	−0.0053 (16)	0.0123 (18)	−0.0043 (17)
C20	0.025 (2)	0.025 (2)	0.074 (3)	−0.0038 (17)	0.023 (2)	−0.005 (2)
C21	0.019 (2)	0.024 (2)	0.031 (2)	−0.0005 (15)	0.0100 (16)	0.0025 (16)
N4	0.0213 (17)	0.0140 (15)	0.0293 (17)	−0.0003 (12)	0.0092 (13)	−0.0001 (13)
C23	0.025 (2)	0.023 (2)	0.071 (3)	−0.0001 (17)	0.023 (2)	−0.011 (2)
N1	0.0244 (17)	0.0182 (16)	0.0264 (17)	0.0042 (12)	0.0104 (14)	0.0006 (13)
N2	0.0265 (17)	0.0127 (16)	0.0304 (17)	0.0036 (12)	0.0086 (14)	0.0024 (12)
N3	0.0238 (17)	0.0149 (16)	0.0341 (17)	−0.0021 (13)	0.0099 (14)	−0.0015 (13)
O1	0.0282 (14)	0.0136 (12)	0.0333 (14)	0.0018 (10)	0.0196 (11)	0.0008 (11)
O2	0.0385 (16)	0.0226 (14)	0.0284 (14)	0.0093 (11)	0.0246 (12)	0.0068 (11)
O1W	0.0230 (15)	0.0157 (14)	0.0277 (15)	0.0028 (11)	0.0138 (12)	−0.0024 (11)
O3	0.0388 (16)	0.0215 (13)	0.0276 (14)	0.0028 (11)	0.0226 (12)	0.0014 (11)
O4	0.0309 (15)	0.0202 (14)	0.0316 (14)	0.0091 (11)	0.0178 (12)	0.0062 (11)
Ni1	0.0259 (3)	0.0180 (2)	0.0269 (3)	0.0016 (2)	0.0137 (2)	0.0008 (2)

Geometric parameters (Å, º) top

C1—O4	1.240 (4)	C16—C17	1.505 (5)
C1—O2	1.270 (4)	C16—H16A	0.9700
C1—C2	1.508 (4)	C16—H16B	0.9700
C2—C3	1.356 (4)	C17—C18	1.525 (4)
C2—C8	1.434 (4)	C17—H17A	0.9700
C3—C4	1.400 (4)	C17—H17B	0.9700
C3—H3	0.9300	C18—C19	1.515 (4)
C4—C5	1.375 (4)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C7	1.420 (4)	C19—N3	1.466 (4)
C5—C6	1.500 (4)	C19—H19A	0.9700
C6—O3	1.240 (4)	C19—H19B	0.9700
C6—O1	1.279 (4)	C20—C23	1.338 (5)
C7—C12	1.421 (4)	C20—N3	1.368 (4)
C7—C8	1.424 (4)	C20—H20	0.9300
C8—C9	1.412 (4)	C21—N4	1.306 (4)
C9—C10	1.356 (4)	C21—N3	1.341 (4)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.392 (5)	N4—C23	1.367 (4)
C10—H10	0.9300	N4—Ni1ⁱ	2.099 (3)
C11—C12	1.347 (4)	C23—H23	0.9300
C11—H11	0.9300	O1—Ni1ⁱⁱ	2.116 (2)
C12—H12	0.9300	O1W—HW12	0.819 (16)
C13—C14	1.343 (5)	O1W—HW11	0.83 (4)
C13—N1	1.355 (4)	O3—Ni1ⁱⁱ	2.347 (2)
C13—H13	0.9300	Ni1—O1W	2.125 (2)
C14—N2	1.363 (4)	Ni1—O2	2.040 (2)
C14—H14	0.9300	Ni1—O1ⁱⁱⁱ	2.116 (2)
C15—N1	1.299 (4)	Ni1—O3ⁱⁱⁱ	2.347 (2)
C15—N2	1.334 (4)	Ni1—N1	2.060 (3)
C15—H15	0.9300	Ni1—N4^iv	2.099 (3)
C16—N2	1.472 (4)

O4—C1—O2	124.8 (3)	H17A—C17—H17B	107.9
O4—C1—C2	120.4 (3)	C19—C18—C17	110.8 (3)
O2—C1—C2	114.8 (3)	C19—C18—H18A	109.5
C3—C2—C8	119.5 (3)	C17—C18—H18A	109.5
C3—C2—C1	118.9 (3)	C19—C18—H18B	109.5
C8—C2—C1	121.5 (3)	C17—C18—H18B	109.5
C2—C3—C4	121.6 (3)	H18A—C18—H18B	108.1
C2—C3—H3	119.2	N3—C19—C18	113.0 (3)
C4—C3—H3	119.2	N3—C19—H19A	109.0
C5—C4—C3	121.1 (3)	C18—C19—H19A	109.0
C5—C4—H4	119.5	N3—C19—H19B	109.0
C3—C4—H4	119.5	C18—C19—H19B	109.0
C4—C5—C7	119.2 (3)	H19A—C19—H19B	107.8
C4—C5—C6	119.1 (3)	C23—C20—N3	106.2 (3)
C7—C5—C6	121.7 (3)	C23—C20—H20	126.9
O3—C6—O1	120.7 (3)	N3—C20—H20	126.9
O3—C6—C5	121.2 (3)	N4—C21—N3	112.7 (3)
O1—C6—C5	118.1 (3)	N4—C21—H21	123.6
C5—C7—C12	122.5 (3)	N3—C21—H21	123.6
C5—C7—C8	119.6 (3)	C21—N4—C23	104.3 (3)
C12—C7—C8	117.8 (3)	C21—N4—Ni1ⁱ	128.0 (2)
C9—C8—C7	118.6 (3)	C23—N4—Ni1ⁱ	127.4 (2)
C9—C8—C2	122.4 (3)	C20—C23—N4	110.8 (3)
C7—C8—C2	118.9 (3)	C20—C23—H23	124.6
C10—C9—C8	121.5 (3)	N4—C23—H23	124.6
C10—C9—H9	119.2	C15—N1—C13	104.8 (3)
C8—C9—H9	119.2	C15—N1—Ni1	126.0 (2)
C9—C10—C11	119.7 (3)	C13—N1—Ni1	129.1 (2)
C9—C10—H10	120.2	C15—N2—C14	105.8 (3)
C11—C10—H10	120.2	C15—N2—C16	126.7 (3)
C12—C11—C10	121.3 (3)	C14—N2—C16	127.5 (3)
C12—C11—H11	119.4	C21—N3—C20	106.0 (3)
C10—C11—H11	119.4	C21—N3—C19	125.8 (3)
C11—C12—C7	121.1 (3)	C20—N3—C19	128.1 (3)
C11—C12—H12	119.5	C6—O1—Ni1ⁱⁱ	94.87 (19)
C7—C12—H12	119.5	C1—O2—Ni1	130.1 (2)
C14—C13—N1	110.2 (3)	Ni1—O1W—HW12	126 (2)
C14—C13—H13	124.9	Ni1—O1W—HW11	97 (3)
N1—C13—H13	124.9	HW12—O1W—HW11	110 (2)
C13—C14—N2	106.3 (3)	C6—O3—Ni1ⁱⁱ	85.3 (2)
C13—C14—H14	126.9	O2—Ni1—N1	85.93 (10)
N2—C14—H14	126.9	O2—Ni1—N4^iv	102.65 (10)
N1—C15—N2	112.9 (3)	N1—Ni1—N4^iv	96.70 (11)
N1—C15—H15	123.6	O2—Ni1—O1ⁱⁱⁱ	159.34 (9)
N2—C15—H15	123.6	N1—Ni1—O1ⁱⁱⁱ	94.01 (10)
N2—C16—C17	112.4 (3)	N4^iv—Ni1—O1ⁱⁱⁱ	97.87 (10)
N2—C16—H16A	109.1	O2—Ni1—O1W	85.20 (9)
C17—C16—H16A	109.1	N1—Ni1—O1W	169.33 (10)
N2—C16—H16B	109.1	N4^iv—Ni1—O1W	91.03 (10)
C17—C16—H16B	109.1	O1ⁱⁱⁱ—Ni1—O1W	92.20 (9)
H16A—C16—H16B	107.9	O2—Ni1—O3ⁱⁱⁱ	100.97 (9)
C16—C17—C18	111.9 (3)	N1—Ni1—O3ⁱⁱⁱ	86.35 (10)
C16—C17—H17A	109.2	N4^iv—Ni1—O3ⁱⁱⁱ	156.33 (9)
C18—C17—H17A	109.2	O1ⁱⁱⁱ—Ni1—O3ⁱⁱⁱ	58.47 (8)
C16—C17—H17B	109.2	O1W—Ni1—O3ⁱⁱⁱ	89.53 (8)
C18—C17—H17B	109.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O1^v	0.82 (2)	1.85 (2)	2.661 (3)	172 (3)
O1W—HW11···O4	0.83 (4)	1.83 (4)	2.651 (3)	169 (3)

Symmetry code: (v) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₆O₄)(C₁₀H₁₄N₄)(H₂O)]
M_r	481.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.4213 (12), 13.2543 (13), 13.4328 (13)
β (°)	107.361 (2)
V (Å³)	2110.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.19 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.827, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	11720, 4157, 2982
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.097, 1.05
No. of reflections	4157
No. of parameters	297
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)	0.54, −0.40

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

Selected bond lengths (Å) top

Ni1—O1W	2.125 (2)	Ni1—O3ⁱ	2.347 (2)
Ni1—O2	2.040 (2)	Ni1—N1	2.060 (3)
Ni1—O1ⁱ	2.116 (2)	Ni1—N4ⁱⁱ	2.099 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O1ⁱⁱⁱ	0.819 (16)	1.847 (18)	2.661 (3)	172 (3)
O1W—HW11···O4	0.83 (4)	1.83 (4)	2.651 (3)	169 (3)

Symmetry code: (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The author thanks Beihua University for supporting this work.

References

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494. Web of Science CrossRef Google Scholar
Bruker (1998). SMART, SAINT and SADABS. 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

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