Triaqua­(2,2′-bipyridine)(5-nitro­isophthal­ato-κO)nickel(II) monohydrate

Liu, Y.; He, Q.; Zhang, X.; Xue, Z.; Lv, C.

doi:10.1107/S1600536808038233

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m27

doi:10.1107/S1600536808038233

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Triaqua(2,2′-bipyridine)(5-nitroisophthalato-κO)nickel(II) monohydrate

Ying Liu,^a ^* Qingpeng He,^a Xianxi Zhang,^a Zechun Xue ^a and Chunyan Lv ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: yllctu@yahoo.com.cn

(Received 9 November 2008; accepted 17 November 2008; online 10 December 2008)

In the title compound, [Ni(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O, the Ni^II cation is six-coordinated by a chelating 2,2′-bipyridine ligand, one carboxylate O atom from a 5-nitroisophthalate dianion and three water molecules, with a slightly distorted cis-NiN₂O₄ octahedral geometry. The neutral complex is isolated, in contrast to coordination polymers formed by Mn^II, Co^II and Cu^II with the same ligand set, but forms an extensive network of O—H⋯O hydrogen bonds between the coordinated and uncoordinated water molecules and carboxylate groups of the 5-nitroisophthalate ions.

Related literature

For the related coordination polymers containing Co^II, Mn^II and Cu^II, see: Xiao et al. (2005 ); Xie et al. (2005 , 2006 ), respectively. For background, see: Kim et al. (2001 ).

Experimental

Crystal data

[Ni(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O
M_r = 496.05
Triclinic, $[P \overline 1]$
a = 7.4867 (10) Å
b = 10.717 (3) Å
c = 12.773 (2) Å
α = 89.798 (10)°
β = 87.89 (2)°
γ = 74.675 (10)°
V = 987.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.885, T_max = 0.921
5649 measured reflections
3823 independent reflections
3271 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.01
3823 reflections
314 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.051 (2)
Ni1—O2W	2.079 (2)
Ni1—O1W	2.088 (2)
Ni1—O3W	2.142 (2)
Ni1—N2	2.097 (2)
Ni1—N3	2.100 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2	0.81 (3)	2.00 (3)	2.727 (3)	150 (5)
O1W—H2W⋯O4ⁱ	0.82 (4)	1.96 (5)	2.715 (3)	154 (4)
O2W—H3W⋯O4Wⁱⁱ	0.82 (3)	1.82 (4)	2.614 (4)	166 (4)
O2W—H4W⋯O4ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.757 (3)	164 (4)
O3W—H5W⋯O4W^iv	0.82 (4)	2.42 (2)	3.185 (7)	156 (5)
O3W—H6W⋯O4^v	0.82 (3)	1.97 (2)	2.735 (3)	155 (4)
O4W—H7W⋯O2^vi	0.81 (4)	1.91 (2)	2.697 (4)	161 (5)
O4W—H8W⋯O3^vii	0.81 (3)	1.98 (4)	2.639 (4)	138 (5)
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z+1; (iii) x+1, y-1, z; (iv) x, y-1, z+1; (v) -x+1, -y+1, -z+2; (vi) -x+1, -y+1, -z+1; (vii) x+1, y, z-1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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/S1600536808038233/hb2841sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038233/hb2841Isup2.hkl

checkCIF report

Comment top

In recent years, carboxylic acids have been widely used in materials science as polydentate ligands which can coordinate to transition-metal or rare-earth cations to yield complexes with interesting or useful properties. For example, Kim et al. (2001) have focused on the syntheses of transition-metal complexes containing benzene carboxylate and rigid aromatic pyridine ligands in order to study their electronic conductivity and magnetic properties. The importance of transition-metal dicarboxylate complexes motivated us to pursue synthetic strategies for these compounds, using 5-nitroisophthalic acid as a polydentate ligand and we now report the synthesis and structure of the title compound, (I) (Fig. 1).

The Ni^II cation in (I) is hexa-coordinated by a chelating 2,2'-bipyridine ligand, one carboxylate O atom from a 5-nitroisophthalate dianion and three water molecules, with a slightly distorted cis-NiN₂O₄ octahedral geometry (Table 1). The neutral complex is isolated, in contrast to coordination polymers formed by Mn^II, Co^II and Cu^II with the same ligand set, but forms an extensive network of O—H···O hydrogen bonds (Table 2) between the coordinated and uncoordinated water molecules and carboxylate groups of the 5-nitroisophthalate ions.

Related literature top

For the related coordination polymers containing Co^II, Mn^II and Cu^II, see: Xiao et al. (2005); Xie et al. (2005; Xie et al., 2006), respectively. For background, see: Kim et al. (2001).

Experimental top

A mixture of nickel dichloride (0.5 mmol), 2,2'-bipyridine (0.5 mmol), and 5-nitroisophthalic acid (0.5 mmol) in H₂O (8 ml) and ethanol (8 ml) was sealed in a 25-ml Teflon-lined stainless steel autoclave and heated to 413 K for three days. Green blocks of (I) were obtained after cooling to room temperature with a yield of 27%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. A view of the molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms.

Triaqua(2,2'-bipyridine)(5-nitroisophthalato-κO)nickel(II) monohydrate top

Crystal data top

[Ni(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O	Z = 2
M_r = 496.05	F(000) = 512
Triclinic, P1	D_x = 1.668 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4867 (10) Å	Cell parameters from 3823 reflections
b = 10.717 (3) Å	θ = 1.6–26.0°
c = 12.773 (2) Å	µ = 1.05 mm⁻¹
α = 89.798 (10)°	T = 293 K
β = 87.89 (2)°	Block, green
γ = 74.675 (10)°	0.12 × 0.10 × 0.08 mm
V = 987.7 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3823 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.885, T_max = 0.921	k = −13→11
5649 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: difmap and geom
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.071P)² + 0.9983P] where P = (F_o² + 2F_c²)/3
3823 reflections	(Δ/σ)_max < 0.001
314 parameters	Δρ_max = 0.99 e Å⁻³
12 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[Ni(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O	γ = 74.675 (10)°
M_r = 496.05	V = 987.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.4867 (10) Å	Mo Kα radiation
b = 10.717 (3) Å	µ = 1.05 mm⁻¹
c = 12.773 (2) Å	T = 293 K
α = 89.798 (10)°	0.12 × 0.10 × 0.08 mm
β = 87.89 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3823 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3271 reflections with I > 2σ(I)
T_min = 0.885, T_max = 0.921	R_int = 0.016
5649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	12 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.99 e Å⁻³
3823 reflections	Δρ_min = −0.73 e Å⁻³
314 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
Ni1	0.72908 (5)	−0.02881 (3)	0.78571 (3)	0.02430 (16)
C1	0.8232 (5)	−0.3096 (3)	0.8659 (2)	0.0303 (7)
H1	0.7701	−0.2738	0.9296	0.036*
C2	0.8972 (5)	−0.4404 (3)	0.8591 (3)	0.0371 (8)
H2	0.8903	−0.4931	0.9163	0.044*
C3	0.9816 (5)	−0.4922 (3)	0.7667 (3)	0.0385 (8)
H3	1.0368	−0.5807	0.7612	0.046*
C4	0.9848 (5)	−0.4139 (3)	0.6820 (3)	0.0321 (7)
H4	1.0424	−0.4480	0.6187	0.038*
C5	0.9009 (4)	−0.2836 (3)	0.6926 (2)	0.0227 (6)
C6	0.8764 (4)	−0.1940 (3)	0.6036 (2)	0.0254 (6)
C7	0.7338 (5)	0.0090 (3)	0.5475 (3)	0.0360 (8)
H7	0.6633	0.0927	0.5628	0.043*
C8	0.7884 (6)	−0.0224 (4)	0.4454 (3)	0.0476 (9)
H8	0.7524	0.0376	0.3922	0.057*
C9	0.8975 (7)	−0.1445 (4)	0.4233 (3)	0.0532 (11)
H9	0.9406	−0.1680	0.3551	0.064*
C10	0.9418 (6)	−0.2309 (4)	0.5028 (3)	0.0429 (9)
H10	1.0157	−0.3141	0.4893	0.052*
C11	0.5174 (4)	0.2464 (3)	0.8072 (3)	0.0296 (7)
C12	0.4966 (4)	0.3864 (3)	0.7871 (2)	0.0245 (6)
C13	0.4091 (4)	0.4774 (3)	0.8608 (2)	0.0244 (6)
H13	0.3675	0.4506	0.9243	0.029*
C14	0.3821 (4)	0.6079 (3)	0.8421 (2)	0.0218 (6)
C15	0.2887 (4)	0.7042 (3)	0.9250 (2)	0.0229 (6)
C16	0.4381 (4)	0.6470 (3)	0.7464 (2)	0.0242 (6)
H16	0.4168	0.7345	0.7311	0.029*
C17	0.5258 (4)	0.5548 (3)	0.6739 (2)	0.0237 (6)
C18	0.5605 (4)	0.4251 (3)	0.6923 (2)	0.0267 (6)
H18	0.6250	0.3647	0.6429	0.032*
H1W	0.394 (6)	0.0433 (19)	0.814 (4)	0.080*
H2W	0.430 (7)	−0.089 (3)	0.824 (3)	0.080*
H3W	1.002 (7)	0.0536 (18)	0.815 (4)	0.080*
H4W	1.071 (6)	−0.077 (3)	0.827 (3)	0.080*
H5W	0.784 (5)	−0.065 (3)	0.979 (4)	0.080*
H6W	0.696 (6)	0.062 (2)	0.980 (4)	0.080*
H7W	0.857 (4)	0.785 (5)	0.129 (4)	0.080*
H8W	1.005 (6)	0.792 (5)	0.064 (2)	0.080*
N1	0.5843 (4)	0.5975 (3)	0.5725 (2)	0.0317 (6)
N2	0.7764 (3)	−0.0739 (2)	0.62575 (19)	0.0254 (5)
N3	0.8242 (3)	−0.2316 (2)	0.78473 (18)	0.0236 (5)
O1	0.6531 (3)	0.16736 (19)	0.76279 (17)	0.0296 (5)
O2	0.3983 (4)	0.2176 (2)	0.8663 (3)	0.0569 (8)
O3	0.2273 (3)	0.6637 (2)	1.00532 (18)	0.0380 (6)
O4	0.2779 (3)	0.82113 (19)	0.90681 (17)	0.0294 (5)
O5	0.5189 (4)	0.7083 (2)	0.54771 (19)	0.0495 (7)
O6	0.6974 (4)	0.5196 (2)	0.51729 (18)	0.0413 (6)
O1W	0.4496 (3)	−0.0279 (2)	0.79179 (19)	0.0316 (5)
O2W	1.0016 (3)	−0.0185 (2)	0.79477 (19)	0.0318 (5)
O3W	0.7027 (4)	−0.0088 (2)	0.95279 (18)	0.0391 (6)
O4W	0.9500 (5)	0.8091 (4)	0.1199 (5)	0.115 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0280 (2)	0.0187 (2)	0.0255 (2)	−0.00530 (16)	0.00210 (15)	−0.00138 (14)
C1	0.0380 (18)	0.0296 (16)	0.0247 (15)	−0.0118 (14)	−0.0005 (13)	0.0040 (12)
C2	0.043 (2)	0.0311 (18)	0.0399 (19)	−0.0143 (15)	−0.0094 (15)	0.0133 (14)
C3	0.043 (2)	0.0190 (15)	0.051 (2)	−0.0035 (14)	−0.0063 (16)	0.0027 (14)
C4	0.0348 (17)	0.0220 (15)	0.0365 (17)	−0.0031 (13)	0.0035 (14)	−0.0048 (13)
C5	0.0252 (15)	0.0196 (14)	0.0234 (14)	−0.0059 (11)	0.0000 (11)	−0.0005 (11)
C6	0.0297 (16)	0.0206 (14)	0.0260 (15)	−0.0072 (12)	0.0024 (12)	−0.0012 (11)
C7	0.046 (2)	0.0288 (17)	0.0308 (17)	−0.0059 (15)	−0.0046 (14)	0.0077 (13)
C8	0.072 (3)	0.043 (2)	0.0282 (18)	−0.016 (2)	−0.0062 (17)	0.0108 (15)
C9	0.086 (3)	0.051 (2)	0.0237 (17)	−0.023 (2)	0.0098 (18)	−0.0020 (16)
C10	0.064 (2)	0.0338 (18)	0.0284 (17)	−0.0100 (17)	0.0155 (16)	−0.0061 (14)
C11	0.0266 (16)	0.0163 (14)	0.0451 (18)	−0.0048 (12)	0.0056 (14)	−0.0013 (13)
C12	0.0228 (14)	0.0147 (13)	0.0349 (16)	−0.0032 (11)	0.0015 (12)	0.0003 (11)
C13	0.0242 (15)	0.0192 (14)	0.0292 (15)	−0.0053 (11)	0.0028 (12)	0.0023 (11)
C14	0.0218 (14)	0.0180 (14)	0.0256 (14)	−0.0053 (11)	−0.0004 (11)	0.0000 (11)
C15	0.0230 (14)	0.0168 (13)	0.0276 (15)	−0.0030 (11)	−0.0022 (11)	0.0005 (11)
C16	0.0289 (15)	0.0158 (13)	0.0284 (15)	−0.0069 (11)	−0.0034 (12)	0.0014 (11)
C17	0.0274 (15)	0.0230 (14)	0.0210 (14)	−0.0069 (12)	−0.0013 (11)	−0.0001 (11)
C18	0.0287 (15)	0.0210 (14)	0.0296 (15)	−0.0053 (12)	0.0009 (12)	−0.0049 (12)
N1	0.0414 (16)	0.0322 (15)	0.0241 (13)	−0.0147 (12)	−0.0001 (11)	−0.0007 (11)
N2	0.0306 (13)	0.0224 (12)	0.0237 (12)	−0.0079 (10)	−0.0006 (10)	0.0018 (10)
N3	0.0288 (13)	0.0186 (12)	0.0234 (12)	−0.0066 (10)	−0.0006 (10)	−0.0007 (9)
O1	0.0319 (12)	0.0136 (10)	0.0401 (12)	−0.0018 (8)	0.0103 (10)	−0.0012 (8)
O2	0.0483 (16)	0.0202 (12)	0.100 (2)	−0.0103 (11)	0.0408 (16)	−0.0044 (13)
O3	0.0522 (15)	0.0225 (11)	0.0353 (12)	−0.0055 (10)	0.0178 (11)	0.0009 (9)
O4	0.0399 (12)	0.0151 (10)	0.0314 (11)	−0.0049 (9)	0.0044 (9)	−0.0014 (8)
O5	0.080 (2)	0.0305 (14)	0.0337 (13)	−0.0095 (13)	0.0069 (13)	0.0105 (10)
O6	0.0484 (15)	0.0429 (14)	0.0293 (12)	−0.0085 (12)	0.0131 (11)	−0.0061 (10)
O1W	0.0281 (12)	0.0221 (11)	0.0443 (13)	−0.0073 (9)	0.0061 (10)	0.0013 (10)
O2W	0.0297 (12)	0.0237 (11)	0.0424 (13)	−0.0070 (9)	−0.0075 (10)	0.0023 (10)
O3W	0.0660 (18)	0.0267 (12)	0.0248 (11)	−0.0132 (12)	0.0003 (11)	−0.0043 (9)
O4W	0.0426 (19)	0.079 (3)	0.227 (6)	−0.0297 (18)	0.054 (3)	−0.107 (3)

Geometric parameters (Å, º) top

Ni1—O1	2.051 (2)	C11—O2	1.246 (4)
Ni1—O2W	2.079 (2)	C11—O1	1.256 (4)
Ni1—O1W	2.088 (2)	C11—C12	1.490 (4)
Ni1—O3W	2.142 (2)	C12—C13	1.375 (4)
Ni1—N2	2.097 (2)	C12—C18	1.387 (4)
Ni1—N3	2.100 (2)	C13—C14	1.380 (4)
C1—N3	1.331 (4)	C13—H13	0.9300
C1—C2	1.365 (5)	C14—C16	1.377 (4)
C1—H1	0.9300	C14—C15	1.499 (4)
C2—C3	1.366 (5)	C15—O3	1.232 (4)
C2—H2	0.9300	C15—O4	1.256 (3)
C3—C4	1.371 (5)	C16—C17	1.372 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.376 (4)	C17—C18	1.366 (4)
C4—H4	0.9300	C17—N1	1.463 (4)
C5—N3	1.345 (4)	C18—H18	0.9300
C5—C6	1.471 (4)	N1—O5	1.205 (4)
C6—N2	1.331 (4)	N1—O6	1.224 (3)
C6—C10	1.382 (4)	O1W—H1W	0.81 (3)
C7—N2	1.326 (4)	O1W—H2W	0.82 (4)
C7—C8	1.369 (5)	O2W—H3W	0.82 (3)
C7—H7	0.9300	O2W—H4W	0.82 (4)
C8—C9	1.371 (6)	O3W—H5W	0.82 (4)
C8—H8	0.9300	O3W—H6W	0.82 (3)
C9—C10	1.361 (5)	O4W—H7W	0.81 (4)
C9—H9	0.9300	O4W—H8W	0.81 (3)
C10—H10	0.9300

O1—Ni1—O2W	88.23 (9)	O2—C11—O1	125.6 (3)
O1—Ni1—O1W	89.39 (9)	O2—C11—C12	117.3 (3)
O2W—Ni1—O1W	173.81 (9)	O1—C11—C12	117.1 (3)
O1—Ni1—N2	94.35 (9)	C13—C12—C18	120.0 (3)
O2W—Ni1—N2	89.63 (10)	C13—C12—C11	120.1 (3)
O1W—Ni1—N2	96.25 (10)	C18—C12—C11	119.9 (3)
O1—Ni1—N3	170.92 (9)	C14—C13—C12	121.1 (3)
O2W—Ni1—N3	89.18 (9)	C14—C13—H13	119.5
O1W—Ni1—N3	94.02 (9)	C12—C13—H13	119.5
N2—Ni1—N3	76.92 (9)	C13—C14—C16	119.1 (3)
O1—Ni1—O3W	93.00 (9)	C13—C14—C15	119.5 (3)
O2W—Ni1—O3W	88.23 (10)	C16—C14—C15	121.3 (3)
O1W—Ni1—O3W	86.19 (10)	O3—C15—O4	124.8 (3)
N2—Ni1—O3W	172.27 (9)	O3—C15—C14	118.2 (2)
N3—Ni1—O3W	95.62 (9)	O4—C15—C14	117.1 (3)
N3—C1—C2	122.5 (3)	C17—C16—C14	119.0 (3)
N3—C1—H1	118.8	C17—C16—H16	120.5
C2—C1—H1	118.8	C14—C16—H16	120.5
C1—C2—C3	118.7 (3)	C18—C17—C16	122.9 (3)
C1—C2—H2	120.7	C18—C17—N1	118.6 (3)
C3—C2—H2	120.6	C16—C17—N1	118.5 (3)
C2—C3—C4	120.0 (3)	C17—C18—C12	117.8 (3)
C2—C3—H3	120.0	C17—C18—H18	121.1
C4—C3—H3	120.0	C12—C18—H18	121.1
C3—C4—C5	118.5 (3)	O5—N1—O6	123.2 (3)
C3—C4—H4	120.8	O5—N1—C17	118.1 (3)
C5—C4—H4	120.8	O6—N1—C17	118.7 (3)
N3—C5—C4	121.7 (3)	C7—N2—C6	118.3 (3)
N3—C5—C6	115.5 (2)	C7—N2—Ni1	125.9 (2)
C4—C5—C6	122.7 (3)	C6—N2—Ni1	115.4 (2)
N2—C6—C10	121.4 (3)	C1—N3—C5	118.7 (3)
N2—C6—C5	114.9 (3)	C1—N3—Ni1	126.6 (2)
C10—C6—C5	123.5 (3)	C5—N3—Ni1	114.67 (18)
N2—C7—C8	123.3 (3)	C11—O1—Ni1	125.67 (19)
N2—C7—H7	118.4	Ni1—O1W—H1W	105 (4)
C8—C7—H7	118.4	Ni1—O1W—H2W	113 (4)
C9—C8—C7	118.3 (3)	H1W—O1W—H2W	116 (3)
C9—C8—H8	120.8	Ni1—O2W—H3W	109 (3)
C7—C8—H8	120.8	Ni1—O2W—H4W	116 (4)
C10—C9—C8	119.0 (3)	H3W—O2W—H4W	113 (3)
C10—C9—H9	120.5	Ni1—O3W—H5W	109 (3)
C8—C9—H9	120.5	Ni1—O3W—H6W	120 (4)
C9—C10—C6	119.6 (3)	H5W—O3W—H6W	111 (3)
C9—C10—H10	120.2	H7W—O4W—H8W	116 (3)
C6—C10—H10	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.81 (3)	2.00 (3)	2.727 (3)	150 (5)
O1W—H2W···O4ⁱ	0.82 (4)	1.96 (5)	2.715 (3)	154 (4)
O2W—H3W···O4Wⁱⁱ	0.82 (3)	1.82 (4)	2.614 (4)	166 (4)
O2W—H4W···O4ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.757 (3)	164 (4)
O3W—H5W···O4W^iv	0.82 (4)	2.42 (2)	3.185 (7)	156 (5)
O3W—H6W···O4^v	0.82 (3)	1.97 (2)	2.735 (3)	155 (4)
O4W—H7W···O2^vi	0.81 (4)	1.91 (2)	2.697 (4)	161 (5)
O4W—H8W···O3^vii	0.81 (3)	1.98 (4)	2.639 (4)	138 (5)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)₃]·H₂O
M_r	496.05
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4867 (10), 10.717 (3), 12.773 (2)
α, β, γ (°)	89.798 (10), 87.89 (2), 74.675 (10)
V (Å³)	987.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.885, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	5649, 3823, 3271
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.01
No. of reflections	3823
No. of parameters	314
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.73

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O1	2.051 (2)	Ni1—O3W	2.142 (2)
Ni1—O2W	2.079 (2)	Ni1—N2	2.097 (2)
Ni1—O1W	2.088 (2)	Ni1—N3	2.100 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.81 (3)	2.00 (3)	2.727 (3)	150 (5)
O1W—H2W···O4ⁱ	0.82 (4)	1.96 (5)	2.715 (3)	154 (4)
O2W—H3W···O4Wⁱⁱ	0.82 (3)	1.82 (4)	2.614 (4)	166 (4)
O2W—H4W···O4ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.757 (3)	164 (4)
O3W—H5W···O4W^iv	0.82 (4)	2.42 (2)	3.185 (7)	156 (5)
O3W—H6W···O4^v	0.82 (3)	1.97 (2)	2.735 (3)	155 (4)
O4W—H7W···O2^vi	0.81 (4)	1.91 (2)	2.697 (4)	161 (5)
O4W—H8W···O3^vii	0.81 (3)	1.98 (4)	2.639 (4)	138 (5)

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

Acknowledgements

The authors thank the NSFC (grant No. 20501011) and Liaocheng University for financial support (grant No. X071011).

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Xiao, H. P., Li, X.-H. & Cheng, Y.-Q. (2005). Acta Cryst. E61, m158–m159. Web of Science CSD CrossRef IUCr Journals Google Scholar
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