Tetra­aqua­bis­[4-(4H-1,2,4-triazol-4-yl)benzoato-κN1]nickel(II) deca­hydrate

Sun, W.; Yu, Y.; Wang, G.; Wu, X.

doi:10.1107/S1600536811051063

metal-organic compounds

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Volume 68| Part 1| January 2012| Page m10

doi:10.1107/S1600536811051063

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Tetraaquabis[4-(4H-1,2,4-triazol-4-yl)benzoato-κN¹]nickel(II) decahydrate

Weixuan Sun,^a Yaqin Yu,^a Guanjun Wang ^b ^* and Xiaohui Wu ^c

^aDepartment of Preventive Medicine, School of Public Health, Jilin University, Changchun 130021, People's Republic of China, ^bDepartment of Hematology, the First Hospital of Jilin University, Changchun 130021, People's Republic of China, and ^cSchool of Public Health, Jilin University, Changchun 130021, People's Republic of China
^*Correspondence e-mail: doctorwanggj@163.com

(Received 19 November 2011; accepted 28 November 2011; online 3 December 2011)

In the title compound, [Ni(C₉H₆N₃O₂)₂(H₂O)₄]·10H₂O, the Ni^II ion lies on a twofold rotation axis and displays a slightly distorted octahedral geometry defined by two N atoms from two monodentate 4-(1,2,4-triazol-4-yl)benzoate ligands and four water molecules, two of which also lie on the twofold rotation axis. In the crystal, the complex molecules and uncoordinated water molecules are linked via intermolecular O—H⋯N and O—H⋯O hydrogen bonds, forming a three-dimensional supramolecular network. π–π interactions between the benzene rings provide additional stability of the crystal packing [centroid–centroid distance = 3.792 (2) Å].

Related literature

For general background to the applications and structures of metal coordination polymers, see: Rowsell & Yaghi (2005 ); Su et al. (2010 ); Wang et al. (2009 ); Zhang & Chen (2008 ). For a related structure, see: Cui & Zhao (2011 ).

Experimental

Crystal data

[Ni(C₉H₆N₃O₂)₂(H₂O)₄]·10H₂O
M_r = 687.25
Monoclinic, C 2/c
a = 25.840 (3) Å
b = 7.8664 (8) Å
c = 16.8013 (17) Å
β = 112.712 (1)°
V = 3150.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.83, T_max = 0.90
8290 measured reflections
3079 independent reflections
2273 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.119
S = 1.04
3079 reflections
238 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.84 (2)	1.93 (2)	2.751 (3)	167 (4)
O4—H4A⋯O1ⁱⁱ	0.84 (2)	1.86 (2)	2.692 (3)	172 (4)
O5—H5A⋯O8	0.82 (2)	1.94 (2)	2.752 (3)	169 (4)
O5—H5B⋯O7	0.83 (2)	1.84 (2)	2.670 (3)	171 (4)
O6—H6A⋯O7	0.82 (2)	1.95 (2)	2.773 (4)	178 (4)
O6—H6B⋯O10	0.84 (2)	1.91 (3)	2.747 (4)	177 (6)
O7—H7A⋯O2ⁱⁱⁱ	0.84 (2)	1.84 (2)	2.674 (3)	170 (4)
O7—H7B⋯O9^iv	0.84 (2)	1.88 (2)	2.715 (4)	171 (4)
O8—H8A⋯N3^v	0.82 (2)	2.16 (2)	2.943 (3)	160 (4)
O8—H8B⋯O2^vi	0.85 (2)	1.92 (2)	2.763 (3)	175 (4)
O9—H9A⋯O1ⁱⁱ	0.84 (2)	1.93 (2)	2.751 (3)	169 (4)
O9—H9B⋯O8	0.85 (2)	1.93 (2)	2.757 (3)	164 (4)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z; (v) $[x, -y+1, z-{\script{1\over 2}}]$ ; (vi) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051063/hy2491sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051063/hy2491Isup2.hkl

checkCIF report

Comment top

Recently, the chemists have devoted themselves to design and synthesize coordination polymers, not only due to their potential applications in the realm of gas adsorption and separation, catalysis, magnetism, luminescence, host–guest chemistry etc, but also for their aesthetic and often complicated architectures and topologies (Su et al., 2010; Wang et al., 2009). It is well known that carboxylic acids are excellent building blocks for the construction of coordination polymers because the carboxylate groups may induce core aggregation and link these discrete clusters into an extended framework by virtue of its bridging ability (Rowsell & Yaghi, 2005; Zhang & Chen, 2008). Taking these into account, we chose a carboxylate ligand, 4-(1,2,4-triazol-4-yl)benzoic acid, generating the title compound, which is reported here.

In the title compound, the Ni^II ion lies on a twofold rotation axis and displays a slightly distorted octahedral geometry defined by two N atoms from two 4-(1,2,4-triazol-4-yl)benzoate ligands and four water molecules, two of which lie on the twofold rotation axis (Fig. 1). The bond lengths and angles are in a normal range (Cui & Zhao, 2011). In the crystal, the complex molecules and uncoordinated water molecules are linked via intermolecular O—H···N and O—H···O hydrogen bonds, forming a three-dimensional supramolecular network (Fig. 2). π–π interactions between the benzene rings, with a centroid–centroid distance of 3.792 (2) Å, provide additional stability of the crystal packing.

Related literature top

For general background to the applications and structures of metal coordination polymers, see: Rowsell & Yaghi (2005); Su et al. (2010); Wang et al. (2009); Zhang & Chen (2008). For a related structure, see: Cui & Zhao (2011).

Experimental top

The synthesis was performed under hydrothermal conditions. A mixture of Ni(CH₃COO)₂.4H₂O (0.2 mmol, 0.050 g), 4-(1,2,4-triazol-4-yl)benzoic acid (0.4 mmol, 0.075 g), NaOH (0.4 mmol, 0.016 g) and H₂O (15 ml) in a 25 ml stainless steel reactor with a Teflon liner was heated from 293 to 443 K in 2 h and a constant temperature was maintained at 443 K for 72 h. After the mixture was cooled to 298 K, pink crystals of the title compound were obtained from the reaction.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structute of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) 1-x, y, 3/2-z.]
	Fig. 2. View of the three-dimensional structure of the title compound built by hydrogen bonds (dashed lines).

Tetraaquabis[4-(4H-1,2,4-triazol-4-yl)benzoato-κN¹]nickel(II) decahydrate top

Crystal data top

[Ni(C₉H₆N₃O₂)₂(H₂O)₄]·10H₂O	F(000) = 1448
M_r = 687.25	D_x = 1.449 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3079 reflections
a = 25.840 (3) Å	θ = 1.0–25.9°
b = 7.8664 (8) Å	µ = 0.70 mm⁻¹
c = 16.8013 (17) Å	T = 293 K
β = 112.712 (1)°	Block, pink
V = 3150.3 (6) Å³	0.22 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3079 independent reflections
Radiation source: fine-focus sealed tube	2273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −31→31
T_min = 0.83, T_max = 0.90	k = −6→9
8290 measured reflections	l = −20→17

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) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 2.4003P] where P = (F_o² + 2F_c²)/3
3079 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.55 e Å⁻³
14 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Ni(C₉H₆N₃O₂)₂(H₂O)₄]·10H₂O	V = 3150.3 (6) Å³
M_r = 687.25	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.840 (3) Å	µ = 0.70 mm⁻¹
b = 7.8664 (8) Å	T = 293 K
c = 16.8013 (17) Å	0.22 × 0.20 × 0.19 mm
β = 112.712 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3079 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2273 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.90	R_int = 0.057
8290 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	14 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.55 e Å⁻³
3079 reflections	Δρ_min = −0.63 e Å⁻³
238 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.59822 (8)	0.7500	0.01918 (19)
C1	0.83480 (12)	0.4306 (4)	1.04342 (19)	0.0186 (7)
C2	0.79863 (12)	0.3835 (4)	0.96082 (19)	0.0200 (7)
H2	0.8126	0.3236	0.9257	0.024*
C3	0.74225 (13)	0.4242 (4)	0.93015 (19)	0.0205 (7)
H3	0.7182	0.3890	0.8755	0.025*
C4	0.72201 (12)	0.5180 (4)	0.98169 (19)	0.0163 (7)
C5	0.75769 (13)	0.5702 (4)	1.0635 (2)	0.0209 (7)
H5	0.7441	0.6351	1.0975	0.025*
C6	0.81360 (12)	0.5246 (4)	1.0939 (2)	0.0194 (7)
H6	0.8374	0.5575	1.1491	0.023*
C7	0.89538 (13)	0.3748 (4)	1.0778 (2)	0.0196 (7)
C8	0.62534 (12)	0.5537 (4)	0.86818 (19)	0.0192 (7)
H8	0.6334	0.5222	0.8209	0.023*
C9	0.63313 (13)	0.6112 (4)	0.9971 (2)	0.0231 (7)
H9	0.6480	0.6275	1.0565	0.028*
N1	0.66358 (10)	0.5587 (3)	0.95053 (15)	0.0170 (6)
N2	0.57580 (10)	0.5986 (3)	0.86385 (15)	0.0193 (6)
N3	0.58082 (11)	0.6353 (4)	0.94733 (16)	0.0230 (7)
O1	0.92384 (9)	0.3974 (3)	1.15821 (13)	0.0218 (5)
O2	0.91424 (9)	0.3070 (3)	1.02773 (14)	0.0302 (6)
O3	0.5000	0.8594 (4)	0.7500	0.0294 (8)
O4	0.5000	0.3349 (4)	0.7500	0.0228 (7)
O5	0.54970 (9)	0.5800 (3)	0.67831 (14)	0.0211 (5)
O6	0.70477 (12)	0.6665 (4)	0.74921 (19)	0.0430 (7)
O7	0.60752 (10)	0.8271 (3)	0.64103 (15)	0.0280 (6)
O8	0.52147 (10)	0.3127 (3)	0.56372 (15)	0.0255 (6)
O9	0.60244 (10)	0.1461 (3)	0.69923 (16)	0.0315 (6)
O10	0.69525 (11)	0.3274 (4)	0.70686 (17)	0.0363 (7)
H3A	0.5254 (13)	0.921 (4)	0.784 (2)	0.054*
H4A	0.5231 (14)	0.265 (4)	0.783 (2)	0.054*
H5A	0.5411 (17)	0.510 (4)	0.639 (2)	0.054*
H5B	0.5653 (16)	0.656 (4)	0.661 (3)	0.054*
H6A	0.6758 (12)	0.715 (5)	0.718 (2)	0.054*
H6B	0.7026 (18)	0.562 (3)	0.738 (3)	0.054*
H7A	0.6022 (17)	0.833 (5)	0.5885 (14)	0.054*
H7B	0.6041 (18)	0.929 (3)	0.654 (3)	0.054*
H8A	0.5304 (17)	0.319 (6)	0.5218 (19)	0.054*
H8B	0.4879 (10)	0.279 (5)	0.550 (3)	0.054*
H9A	0.5962 (17)	0.146 (6)	0.7445 (18)	0.054*
H9B	0.5732 (12)	0.191 (5)	0.662 (2)	0.054*
H10A	0.7237 (12)	0.268 (5)	0.727 (2)	0.054*
H10B	0.6695 (14)	0.275 (5)	0.712 (3)	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0147 (3)	0.0216 (3)	0.0196 (3)	0.000	0.0049 (2)	0.000
C1	0.0117 (15)	0.0238 (18)	0.0189 (16)	0.0005 (13)	0.0044 (13)	0.0017 (14)
C2	0.0179 (17)	0.0281 (19)	0.0144 (16)	0.0013 (14)	0.0069 (13)	−0.0005 (14)
C3	0.0155 (16)	0.0305 (19)	0.0121 (15)	−0.0005 (14)	0.0014 (12)	0.0006 (14)
C4	0.0105 (15)	0.0197 (16)	0.0172 (16)	0.0021 (13)	0.0035 (13)	0.0023 (14)
C5	0.0188 (17)	0.0258 (19)	0.0174 (16)	0.0041 (14)	0.0062 (13)	−0.0042 (14)
C6	0.0153 (16)	0.0223 (17)	0.0170 (16)	−0.0007 (13)	0.0024 (13)	−0.0029 (14)
C7	0.0145 (16)	0.0217 (18)	0.0214 (17)	0.0004 (13)	0.0057 (14)	0.0031 (15)
C8	0.0144 (16)	0.0263 (18)	0.0148 (15)	0.0000 (13)	0.0034 (13)	−0.0012 (14)
C9	0.0170 (17)	0.037 (2)	0.0146 (16)	0.0034 (15)	0.0055 (13)	−0.0029 (15)
N1	0.0123 (13)	0.0229 (15)	0.0136 (13)	0.0014 (11)	0.0026 (10)	−0.0014 (11)
N2	0.0151 (13)	0.0272 (15)	0.0155 (13)	−0.0008 (12)	0.0058 (11)	−0.0021 (12)
N3	0.0144 (14)	0.0370 (17)	0.0149 (14)	0.0017 (12)	0.0026 (11)	−0.0043 (13)
O1	0.0167 (11)	0.0254 (12)	0.0180 (11)	0.0023 (10)	0.0010 (9)	0.0010 (10)
O2	0.0169 (13)	0.0498 (17)	0.0221 (13)	0.0123 (12)	0.0056 (10)	0.0020 (12)
O3	0.0210 (19)	0.0179 (18)	0.032 (2)	0.000	−0.0087 (15)	0.000
O4	0.0194 (18)	0.0150 (17)	0.0248 (19)	0.000	−0.0015 (14)	0.000
O5	0.0195 (12)	0.0248 (13)	0.0213 (12)	−0.0055 (10)	0.0106 (10)	−0.0034 (10)
O6	0.0341 (17)	0.0381 (17)	0.0489 (18)	0.0012 (14)	0.0073 (14)	0.0007 (15)
O7	0.0318 (14)	0.0289 (14)	0.0249 (13)	−0.0017 (12)	0.0126 (12)	0.0015 (12)
O8	0.0190 (13)	0.0378 (15)	0.0209 (12)	−0.0077 (11)	0.0090 (10)	−0.0023 (11)
O9	0.0255 (14)	0.0388 (15)	0.0315 (15)	0.0064 (12)	0.0123 (12)	0.0047 (13)
O10	0.0282 (16)	0.0390 (17)	0.0373 (16)	−0.0016 (12)	0.0080 (13)	0.0061 (13)

Geometric parameters (Å, º) top

Ni1—O3	2.054 (3)	C8—H8	0.9300
Ni1—O4	2.071 (3)	C9—N3	1.300 (4)
Ni1—O5	2.077 (2)	C9—N1	1.370 (4)
Ni1—N2	2.145 (2)	C9—H9	0.9300
C1—C6	1.387 (4)	N2—N3	1.388 (3)
C1—C2	1.391 (4)	O3—H3A	0.836 (18)
C1—C7	1.510 (4)	O4—H4A	0.840 (18)
C2—C3	1.382 (4)	O5—H5A	0.822 (19)
C2—H2	0.9300	O5—H5B	0.835 (19)
C3—C4	1.385 (4)	O6—H6A	0.824 (19)
C3—H3	0.9300	O6—H6B	0.838 (19)
C4—C5	1.389 (4)	O7—H7A	0.840 (18)
C4—N1	1.430 (4)	O7—H7B	0.844 (19)
C5—C6	1.381 (4)	O8—H8A	0.823 (18)
C5—H5	0.9300	O8—H8B	0.848 (19)
C6—H6	0.9300	O9—H9A	0.836 (19)
C7—O2	1.243 (4)	O9—H9B	0.847 (19)
C7—O1	1.277 (4)	O10—H10A	0.824 (19)
C8—N2	1.303 (4)	O10—H10B	0.817 (19)
C8—N1	1.355 (4)

O3—Ni1—O4	180.000 (2)	C5—C6—C1	121.1 (3)
O3—Ni1—O5ⁱ	93.97 (6)	C5—C6—H6	119.5
O4—Ni1—O5ⁱ	86.03 (7)	C1—C6—H6	119.5
O3—Ni1—O5	93.97 (7)	O2—C7—O1	124.0 (3)
O4—Ni1—O5	86.03 (7)	O2—C7—C1	119.0 (3)
O5ⁱ—Ni1—O5	172.07 (13)	O1—C7—C1	116.9 (3)
O3—Ni1—N2	89.93 (7)	N2—C8—N1	111.3 (3)
O4—Ni1—N2	90.07 (7)	N2—C8—H8	124.4
O5ⁱ—Ni1—N2	92.24 (9)	N1—C8—H8	124.4
O5—Ni1—N2	87.77 (9)	N3—C9—N1	111.2 (3)
O3—Ni1—N2ⁱ	89.93 (7)	N3—C9—H9	124.4
O4—Ni1—N2ⁱ	90.07 (7)	N1—C9—H9	124.4
O5ⁱ—Ni1—N2ⁱ	87.77 (9)	C8—N1—C9	103.8 (3)
O5—Ni1—N2ⁱ	92.24 (9)	C8—N1—C4	128.2 (3)
N2—Ni1—N2ⁱ	179.85 (16)	C9—N1—C4	128.1 (2)
C6—C1—C2	118.7 (3)	C8—N2—N3	107.1 (2)
C6—C1—C7	121.1 (3)	C8—N2—Ni1	126.1 (2)
C2—C1—C7	120.1 (3)	N3—N2—Ni1	126.73 (18)
C3—C2—C1	121.0 (3)	C9—N3—N2	106.7 (2)
C3—C2—H2	119.5	Ni1—O3—H3A	125 (3)
C1—C2—H2	119.5	Ni1—O4—H4A	131 (3)
C2—C3—C4	119.3 (3)	Ni1—O5—H5A	118 (3)
C2—C3—H3	120.4	Ni1—O5—H5B	130 (3)
C4—C3—H3	120.4	H5A—O5—H5B	103 (4)
C3—C4—C5	120.6 (3)	H6A—O6—H6B	110 (4)
C3—C4—N1	119.4 (3)	H7A—O7—H7B	103 (4)
C5—C4—N1	120.0 (3)	H8A—O8—H8B	112 (4)
C6—C5—C4	119.3 (3)	H9A—O9—H9B	103 (4)
C6—C5—H5	120.4	H10A—O10—H10B	108 (4)
C4—C5—H5	120.4

C6—C1—C2—C3	−2.1 (5)	C3—C4—N1—C8	−17.2 (5)
C7—C1—C2—C3	175.9 (3)	C5—C4—N1—C8	163.8 (3)
C1—C2—C3—C4	2.0 (5)	C3—C4—N1—C9	162.5 (3)
C2—C3—C4—C5	−0.3 (5)	C5—C4—N1—C9	−16.5 (5)
C2—C3—C4—N1	−179.3 (3)	N1—C8—N2—N3	−0.1 (4)
C3—C4—C5—C6	−1.3 (5)	N1—C8—N2—Ni1	−176.2 (2)
N1—C4—C5—C6	177.7 (3)	O3—Ni1—N2—C8	−109.7 (3)
C4—C5—C6—C1	1.2 (5)	O4—Ni1—N2—C8	70.3 (3)
C2—C1—C6—C5	0.4 (5)	O5ⁱ—Ni1—N2—C8	156.4 (3)
C7—C1—C6—C5	−177.5 (3)	O5—Ni1—N2—C8	−15.7 (3)
C6—C1—C7—O2	−172.3 (3)	O3—Ni1—N2—N3	75.0 (2)
C2—C1—C7—O2	9.8 (5)	O4—Ni1—N2—N3	−105.0 (2)
C6—C1—C7—O1	9.3 (5)	O5ⁱ—Ni1—N2—N3	−19.0 (3)
C2—C1—C7—O1	−168.6 (3)	O5—Ni1—N2—N3	169.0 (3)
N2—C8—N1—C9	−0.1 (4)	N1—C9—N3—N2	−0.4 (4)
N2—C8—N1—C4	179.7 (3)	C8—N2—N3—C9	0.3 (4)
N3—C9—N1—C8	0.3 (4)	Ni1—N2—N3—C9	176.4 (2)
N3—C9—N1—C4	−179.5 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱⁱ	0.84 (2)	1.93 (2)	2.751 (3)	167 (4)
O4—H4A···O1ⁱⁱⁱ	0.84 (2)	1.86 (2)	2.692 (3)	172 (4)
O5—H5A···O8	0.82 (2)	1.94 (2)	2.752 (3)	169 (4)
O5—H5B···O7	0.83 (2)	1.84 (2)	2.670 (3)	171 (4)
O6—H6A···O7	0.82 (2)	1.95 (2)	2.773 (4)	178 (4)
O6—H6B···O10	0.84 (2)	1.91 (3)	2.747 (4)	177 (6)
O7—H7A···O2^iv	0.84 (2)	1.84 (2)	2.674 (3)	170 (4)
O7—H7B···O9^v	0.84 (2)	1.88 (2)	2.715 (4)	171 (4)
O8—H8A···N3^vi	0.82 (2)	2.16 (2)	2.943 (3)	160 (4)
O8—H8B···O2^vii	0.85 (2)	1.92 (2)	2.763 (3)	175 (4)
O9—H9A···O1ⁱⁱⁱ	0.84 (2)	1.93 (2)	2.751 (3)	169 (4)
O9—H9B···O8	0.85 (2)	1.93 (2)	2.757 (3)	164 (4)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₆N₃O₂)₂(H₂O)₄]·10H₂O
M_r	687.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	25.840 (3), 7.8664 (8), 16.8013 (17)
β (°)	112.712 (1)
V (Å³)	3150.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.83, 0.90
No. of measured, independent and observed [I > 2σ(I)] reflections	8290, 3079, 2273
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.119, 1.04
No. of reflections	3079
No. of parameters	238
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.63

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.84 (2)	1.93 (2)	2.751 (3)	167 (4)
O4—H4A···O1ⁱⁱ	0.84 (2)	1.86 (2)	2.692 (3)	172 (4)
O5—H5A···O8	0.82 (2)	1.94 (2)	2.752 (3)	169 (4)
O5—H5B···O7	0.83 (2)	1.84 (2)	2.670 (3)	171 (4)
O6—H6A···O7	0.82 (2)	1.95 (2)	2.773 (4)	178 (4)
O6—H6B···O10	0.84 (2)	1.91 (3)	2.747 (4)	177 (6)
O7—H7A···O2ⁱⁱⁱ	0.84 (2)	1.84 (2)	2.674 (3)	170 (4)
O7—H7B···O9^iv	0.84 (2)	1.88 (2)	2.715 (4)	171 (4)
O8—H8A···N3^v	0.82 (2)	2.16 (2)	2.943 (3)	160 (4)
O8—H8B···O2^vi	0.85 (2)	1.918 (19)	2.763 (3)	175 (4)
O9—H9A···O1ⁱⁱ	0.84 (2)	1.93 (2)	2.751 (3)	169 (4)
O9—H9B···O8	0.85 (2)	1.93 (2)	2.757 (3)	164 (4)

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

Acknowledgements

The authors thank Jilin University for supporting this work.

References

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