Poly[aqua­[μ2-cis-1,2-bis­(4-pyrid­yl)ethyl­ene-κ2N:N′](μ2-5-nitro­isophthalato-κ3O:O′,O′′)nickel(II)]

Fan, Z.-Z.; Wang, G.-P.; Li, Y.-S.

doi:10.1107/S1600536809053872

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages m80-m81

doi:10.1107/S1600536809053872

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Poly[aqua[μ₂-cis-1,2-bis(4-pyridyl)ethylene-κ²N:N′](μ₂-5-nitroisophthalato-κ³O:O′,O′′)nickel(II)]

Zhen-Zhong Fan,^a ^* Guo-Ping Wang ^b and Yu-Sheng Li ^c

^aDepartment of Petroleum Engineering, Daqing Petroleum Institute, Heilongjiang 151400, People's Republic of China, ^bDepartment of Chemistry, Zhejiang University 310027, People's Republic of China, and ^cSecond Oil Recovery Plant, Daqing Oilfields Co, Daqing 163414, People's Republic of China
^*Correspondence e-mail: chem8618@126.com

(Received 5 December 2009; accepted 14 December 2009; online 19 December 2009)

In the title compound, [Ni(C₈H₃NO₆)(C₁₂H₁₀N₂)(H₂O)]_n, the Ni^II atom is octahedrally coordinated by two cis N atoms from two different 1,2-bis(4-pyridyl)ethylene (bpe) ligands, two O atoms from one chelating carboxyl group of the 5-nitroisophthalic acid (nip) ligand, one O atom from another monodentate nip ligand and one O atom from a water molecule, forming a three-dimensional network structure. Intermolecular O—H⋯O hydrogen bonding stabilizes this arrangement. The asymmetric unit of the structure contains one Ni^II atom, one water molecule, one nip ligand and two half-molecules of the bpe ligand with an inversion centre at the mid-point of the central C=C bond.

Related literature

For structures containing nip ligands, see: Xiao & Yuan (2004 ); Xiao et al. (2005 ). For structures containing bpe ligands, see: Bauer & Weber (2009 ); Jung et al. (2009 ); Zheng & Zhu (2009 ).

Experimental

Crystal data

[Ni(C₈H₃NO₆)(C₁₂H₁₀N₂)(H₂O)]
M_r = 468.06
Triclinic, $[P \overline 1]$
a = 9.3723 (6) Å
b = 10.9947 (7) Å
c = 11.1704 (8) Å
α = 109.970 (1)°
β = 90.190 (1)°
γ = 110.727 (1)°
V = 1001.68 (12) Å³
Z = 2
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.43 × 0.24 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.669, T_max = 0.862
5380 measured reflections
3580 independent reflections
3332 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.089
S = 1.04
3580 reflections
287 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O3ⁱ	2.0326 (14)
Ni1—N1	2.0417 (17)
Ni1—N2	2.0777 (17)
Ni1—O7	2.0797 (15)
Ni1—O1	2.1031 (14)
Ni1—O2	2.2021 (14)
Symmetry code: (i) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7C⋯O4ⁱ	0.82	1.88	2.612 (2)	149
O7—H7B⋯O2ⁱⁱ	0.81 (1)	2.00 (1)	2.786 (2)	163 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 I, global. DOI: 10.1107/S1600536809053872/wm2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053872/wm2289Isup2.hkl

checkCIF report

Comment top

Great interest has recently been focused on the crystal engineering of supramolecular architectures assembled by means of well designed organic ligands and metal ions under appropriate conditions. Previous reports have revealed that carboxylate ligands such as m-isophthalic acid can bind and bridge metal ions in various coordination modes, and bi-functional ligands, such as 4,4,-bipyridine or trans-1,2-bis(4-pyridyl)ethylene (bpe) also can link the metal ions to form network structures (Xiao & Yuan, 2004; Xiao et al., 2005; Bauer & Weber, 2009; Jung et al., 2009; Zheng & Zhu, 2009). Much less is known of systems containing two different ligands. Hence we have employed bpe and 5-nitroisophthalic acid (nip) as ligands in this work. We report herein the new three-dimensional structure of [Ni(nip)(bpe)(H₂O)]_n.

The asymmetric unit of the structure contains one Ni^II atom, one water molecule, one nip ligand and two half-molecules of the N-heterocycle with an inversion centre at the midpoint of the central C═C bond. The Ni1 site shows a slightly distorted octahedron with a NiN2O4 coordination set, as depicted in Fig.1, where the two equatorial N atoms (N1, N2) are from two different bpe ligands, four O atoms from two different nip (O1, O2 and O3ⁱ atoms [symmetry code: (i) x - 1, y, z]), and one water molecule, respectively, with O2 and O3ⁱ atoms [symmetry code: (i) x - 1, y, z] in the axial positions. The metal centres are connected in a three-dimensional fashion through the bpe and nip ligands. The Ni—O and Ni—N bond lengths fall in the ranges 2.0326 (14)–2.2021 (14) Å and 2.0417 (17)–2.0777 (17) Å, respectively. O—H···O hydrogen bonding between the water molecules and the O atoms of the free carboxylate groups stabilizes this assembly. The coordination water molecule forms strong hydrogen bonds O7—H7C···O4ⁱ and O7—H7B···O2^v to the oxygen atoms of the carboxylate anion of the nip ligand (see Table 2). Fig. 2 shows a part of the packed structure of the title compound.

Related literature top

For structures containing nip ligands, see: Xiao & Yuan (2004); Xiao et al. (2005). For structures containing bpe ligands, see: Bauer & Weber (2009); Jung et al. (2009); Zheng & Zhu (2009).

Experimental top

Nickel(II) acetate tetrahydrate (0.5 mmol), 5-nitroisophthalic acid (0.5 mmol) and 1,2-bis(4-pyridyl)ethylene] (0.5 mmol) were placed in a 30 ml teflon-lined, stainless-steel Parr autoclave together with water (20 ml). The autoclave was heated at 423 K for a week and was subsequently cooled slowly to room temperature. Green single crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 coordination of the Ni (II) atom in the structure of the title compound, with atom labels and 50% probability displacement ellipsoids for all non-H atoms. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z.]
	Fig. 2. A part of the network structure of the title compound.

Poly[aqua[µ₂-cis-1,2-bis(4-pyridyl)ethylene- κ²N:N'](µ₂-5-nitroisophthalato- κ³O:O',O'')nickel(II)] top

Crystal data top

[Ni(C₈H₃NO₆)(C₁₂H₁₀N₂)(H₂O)]	Z = 2
M_r = 468.06	F(000) = 480
Triclinic, P1	D_x = 1.552 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3723 (6) Å	Cell parameters from 563 reflections
b = 10.9947 (7) Å	θ = 2.3–25.2°
c = 11.1704 (8) Å	µ = 1.02 mm⁻¹
α = 109.970 (1)°	T = 293 K
β = 90.190 (1)°	Prism, green
γ = 110.727 (1)°	0.43 × 0.24 × 0.15 mm
V = 1001.68 (12) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3580 independent reflections
Radiation source: fine-focus sealed tube	3332 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→11
T_min = 0.669, T_max = 0.862	k = −13→13
5380 measured reflections	l = −13→12

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0584P)² + 0.2791P] where P = (F_o² + 2F_c²)/3
3580 reflections	(Δ/σ)_max = 0.001
287 parameters	Δρ_max = 1.05 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Ni(C₈H₃NO₆)(C₁₂H₁₀N₂)(H₂O)]	γ = 110.727 (1)°
M_r = 468.06	V = 1001.68 (12) Å³
Triclinic, P1	Z = 2
a = 9.3723 (6) Å	Mo Kα radiation
b = 10.9947 (7) Å	µ = 1.02 mm⁻¹
c = 11.1704 (8) Å	T = 293 K
α = 109.970 (1)°	0.43 × 0.24 × 0.15 mm
β = 90.190 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3580 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3332 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.862	R_int = 0.011
5380 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	1 restraint
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.05 e Å⁻³
3580 reflections	Δρ_min = −0.29 e Å⁻³
287 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	−0.10441 (3)	0.65566 (2)	0.40788 (2)	0.02504 (11)
O1	0.08218 (16)	0.83742 (14)	0.52003 (14)	0.0310 (3)
O2	0.12955 (16)	0.65335 (15)	0.40496 (14)	0.0317 (3)
O3	0.72083 (17)	0.72162 (16)	0.46313 (14)	0.0335 (3)
O4	0.7598 (2)	0.76834 (19)	0.67483 (15)	0.0452 (4)
O5	0.7148 (2)	1.2514 (2)	0.8534 (2)	0.0669 (6)
O6	0.4914 (3)	1.2513 (2)	0.8145 (3)	0.0922 (9)
O7	−0.10853 (19)	0.59321 (17)	0.56426 (15)	0.0368 (4)
H7C	−0.1478	0.6361	0.6203	0.055*
N1	−0.2423 (2)	0.45995 (18)	0.28631 (17)	0.0310 (4)
N2	−0.0886 (2)	0.73429 (18)	0.26156 (16)	0.0295 (4)
N3	0.5841 (2)	1.1956 (2)	0.79624 (19)	0.0459 (5)
C1	0.1744 (2)	0.7762 (2)	0.48722 (19)	0.0267 (4)
C2	0.3389 (2)	0.8505 (2)	0.55081 (19)	0.0274 (4)
C3	0.4422 (2)	0.7831 (2)	0.52789 (19)	0.0288 (4)
H3	0.4126	0.6938	0.4655	0.035*
C4	0.5902 (2)	0.8484 (2)	0.59767 (18)	0.0291 (4)
C5	0.6353 (2)	0.9824 (2)	0.6881 (2)	0.0328 (5)
H5	0.7322	1.0259	0.7372	0.039*
C6	0.5339 (2)	1.0506 (2)	0.70426 (19)	0.0314 (4)
C7	0.3861 (2)	0.9872 (2)	0.63851 (19)	0.0307 (4)
H7A	0.3195	1.0348	0.6525	0.037*
C8	0.6993 (2)	0.7724 (2)	0.57767 (19)	0.0296 (4)
C9	−0.1887 (3)	0.3572 (2)	0.2488 (2)	0.0427 (6)
H9	−0.0886	0.3762	0.2815	0.051*
C10	−0.2739 (3)	0.2259 (2)	0.1648 (2)	0.0444 (6)
H10	−0.2310	0.1581	0.1412	0.053*
C11	−0.4237 (3)	0.1925 (2)	0.1143 (2)	0.0363 (5)
C12	−0.4787 (3)	0.2997 (3)	0.1542 (2)	0.0475 (6)
H12	−0.5788	0.2831	0.1235	0.057*
C13	−0.3868 (3)	0.4297 (2)	0.2382 (2)	0.0436 (6)
H13	−0.4263	0.4998	0.2628	0.052*
C14	−0.5208 (3)	0.0535 (3)	0.0252 (2)	0.0428 (5)
C15	−0.0938 (3)	0.6642 (2)	0.1362 (2)	0.0435 (6)
H15	−0.1075	0.5704	0.1097	0.052*
C16	−0.0798 (3)	0.7238 (3)	0.0449 (2)	0.0478 (6)
H16	−0.0861	0.6701	−0.0412	0.057*
C17	−0.0564 (3)	0.8640 (2)	0.0810 (2)	0.0354 (5)
C18	−0.0545 (2)	0.9364 (2)	0.2110 (2)	0.0322 (5)
H18	−0.0422	1.0300	0.2400	0.039*
C19	−0.0710 (2)	0.8682 (2)	0.2961 (2)	0.0309 (4)
H19	−0.0697	0.9182	0.3824	0.037*
C20	−0.0330 (3)	0.9319 (2)	−0.0139 (2)	0.0388 (5)
H20	−0.0673	0.8748	−0.1000	0.047*
H14	−0.618 (3)	0.041 (3)	0.004 (3)	0.047*
H7B	−0.133 (3)	0.5144 (15)	0.564 (3)	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02416 (16)	0.02304 (16)	0.02844 (16)	0.01047 (11)	0.00144 (10)	0.00846 (11)
O1	0.0250 (7)	0.0272 (7)	0.0388 (8)	0.0123 (6)	0.0017 (6)	0.0073 (6)
O2	0.0295 (8)	0.0274 (8)	0.0372 (8)	0.0142 (6)	0.0026 (6)	0.0072 (6)
O3	0.0311 (8)	0.0437 (9)	0.0329 (8)	0.0228 (7)	0.0069 (6)	0.0135 (7)
O4	0.0518 (10)	0.0629 (11)	0.0355 (8)	0.0384 (9)	0.0058 (7)	0.0179 (8)
O5	0.0436 (11)	0.0469 (11)	0.0771 (14)	0.0061 (9)	−0.0101 (10)	−0.0050 (10)
O6	0.0737 (16)	0.0553 (13)	0.114 (2)	0.0416 (12)	−0.0254 (14)	−0.0269 (13)
O7	0.0449 (9)	0.0370 (9)	0.0391 (8)	0.0229 (8)	0.0077 (7)	0.0189 (7)
N1	0.0319 (9)	0.0260 (9)	0.0316 (9)	0.0085 (7)	0.0016 (7)	0.0090 (7)
N2	0.0318 (9)	0.0297 (9)	0.0308 (9)	0.0145 (8)	0.0059 (7)	0.0125 (7)
N3	0.0435 (12)	0.0380 (11)	0.0462 (11)	0.0147 (10)	0.0013 (9)	0.0043 (9)
C1	0.0270 (10)	0.0270 (10)	0.0312 (10)	0.0130 (8)	0.0064 (8)	0.0139 (8)
C2	0.0252 (10)	0.0300 (10)	0.0301 (10)	0.0116 (8)	0.0048 (8)	0.0135 (8)
C3	0.0283 (10)	0.0301 (10)	0.0296 (10)	0.0135 (9)	0.0052 (8)	0.0103 (8)
C4	0.0246 (10)	0.0365 (12)	0.0318 (10)	0.0144 (9)	0.0082 (8)	0.0163 (9)
C5	0.0260 (11)	0.0387 (12)	0.0335 (11)	0.0120 (9)	0.0030 (8)	0.0130 (9)
C6	0.0305 (11)	0.0299 (11)	0.0312 (10)	0.0114 (9)	0.0052 (8)	0.0084 (9)
C7	0.0295 (11)	0.0317 (11)	0.0364 (11)	0.0168 (9)	0.0089 (9)	0.0137 (9)
C8	0.0238 (10)	0.0314 (11)	0.0346 (11)	0.0111 (9)	0.0036 (8)	0.0127 (9)
C9	0.0386 (13)	0.0323 (12)	0.0490 (13)	0.0135 (10)	−0.0102 (10)	0.0054 (10)
C10	0.0458 (14)	0.0309 (12)	0.0492 (14)	0.0160 (11)	−0.0063 (11)	0.0045 (10)
C11	0.0381 (12)	0.0295 (11)	0.0323 (11)	0.0057 (9)	0.0034 (9)	0.0079 (9)
C12	0.0296 (12)	0.0428 (14)	0.0534 (14)	0.0097 (10)	−0.0032 (10)	0.0020 (11)
C13	0.0328 (12)	0.0363 (12)	0.0517 (14)	0.0142 (10)	0.0003 (10)	0.0030 (11)
C14	0.0392 (13)	0.0359 (12)	0.0383 (12)	0.0055 (10)	−0.0005 (10)	0.0049 (10)
C15	0.0657 (17)	0.0315 (12)	0.0374 (12)	0.0226 (11)	0.0145 (11)	0.0130 (10)
C16	0.0717 (18)	0.0380 (13)	0.0313 (11)	0.0197 (12)	0.0149 (11)	0.0110 (10)
C17	0.0340 (12)	0.0387 (12)	0.0363 (11)	0.0129 (10)	0.0078 (9)	0.0178 (10)
C18	0.0343 (11)	0.0307 (11)	0.0354 (11)	0.0144 (9)	0.0061 (9)	0.0144 (9)
C19	0.0323 (11)	0.0306 (11)	0.0314 (10)	0.0144 (9)	0.0046 (8)	0.0107 (9)
C20	0.0433 (13)	0.0434 (12)	0.0324 (11)	0.0161 (10)	0.0059 (10)	0.0174 (10)

Geometric parameters (Å, º) top

Ni1—O3ⁱ	2.0326 (14)	C4—C8	1.507 (3)
Ni1—N1	2.0417 (17)	C5—C6	1.383 (3)
Ni1—N2	2.0777 (17)	C5—H5	0.9300
Ni1—O7	2.0797 (15)	C6—C7	1.380 (3)
Ni1—O1	2.1031 (14)	C7—H7A	0.9300
Ni1—O2	2.2021 (14)	C9—C10	1.363 (3)
Ni1—C1	2.470 (2)	C9—H9	0.9300
O1—C1	1.257 (2)	C10—C11	1.383 (3)
O2—C1	1.262 (2)	C10—H10	0.9300
O3—C8	1.258 (2)	C11—C12	1.388 (3)
O3—Ni1ⁱⁱ	2.0326 (14)	C11—C14	1.458 (3)
O4—C8	1.244 (3)	C12—C13	1.368 (3)
O5—N3	1.217 (3)	C12—H12	0.9300
O6—N3	1.210 (3)	C13—H13	0.9300
O7—H7C	0.8200	C14—C14ⁱⁱⁱ	1.314 (5)
O7—H7B	0.814 (10)	C14—H14	0.89 (3)
N1—C9	1.335 (3)	C15—C16	1.372 (3)
N1—C13	1.337 (3)	C15—H15	0.9300
N2—C19	1.336 (3)	C16—C17	1.387 (3)
N2—C15	1.339 (3)	C16—H16	0.9300
N3—C6	1.471 (3)	C17—C18	1.394 (3)
C1—C2	1.501 (3)	C17—C20	1.468 (3)
C2—C3	1.390 (3)	C18—C19	1.377 (3)
C2—C7	1.391 (3)	C18—H18	0.9300
C3—C4	1.397 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C20^iv	1.322 (5)
C4—C5	1.382 (3)	C20—H20	0.9300

O3ⁱ—Ni1—N1	95.70 (7)	C3—C4—C8	120.55 (18)
O3ⁱ—Ni1—N2	89.29 (6)	C4—C5—C6	118.92 (19)
N1—Ni1—N2	91.76 (7)	C4—C5—H5	120.5
O3ⁱ—Ni1—O7	90.31 (6)	C6—C5—H5	120.5
N1—Ni1—O7	92.91 (7)	C7—C6—C5	122.42 (19)
N2—Ni1—O7	175.33 (6)	C7—C6—N3	118.54 (19)
O3ⁱ—Ni1—O1	98.89 (6)	C5—C6—N3	119.04 (19)
N1—Ni1—O1	165.38 (6)	C6—C7—C2	118.61 (19)
N2—Ni1—O1	89.30 (6)	C6—C7—H7A	120.7
O7—Ni1—O1	86.16 (6)	C2—C7—H7A	120.7
O3ⁱ—Ni1—O2	159.73 (6)	O4—C8—O3	127.14 (19)
N1—Ni1—O2	104.19 (6)	O4—C8—C4	117.32 (18)
N2—Ni1—O2	93.84 (6)	O3—C8—C4	115.52 (17)
O7—Ni1—O2	84.95 (6)	N1—C9—C10	123.1 (2)
O1—Ni1—O2	61.19 (5)	N1—C9—H9	118.5
O3ⁱ—Ni1—C1	129.22 (6)	C10—C9—H9	118.5
N1—Ni1—C1	134.81 (7)	C9—C10—C11	120.5 (2)
N2—Ni1—C1	93.28 (7)	C9—C10—H10	119.7
O7—Ni1—C1	83.37 (6)	C11—C10—H10	119.7
O1—Ni1—C1	30.59 (6)	C10—C11—C12	116.1 (2)
O2—Ni1—C1	30.66 (6)	C10—C11—C14	123.0 (2)
C1—O1—Ni1	91.05 (12)	C12—C11—C14	121.0 (2)
C1—O2—Ni1	86.48 (11)	C13—C12—C11	120.5 (2)
C8—O3—Ni1ⁱⁱ	125.17 (13)	C13—C12—H12	119.7
Ni1—O7—H7C	109.5	C11—C12—H12	119.7
Ni1—O7—H7B	128 (2)	N1—C13—C12	122.6 (2)
H7C—O7—H7B	108.7	N1—C13—H13	118.7
C9—N1—C13	117.23 (19)	C12—C13—H13	118.7
C9—N1—Ni1	120.54 (15)	C14ⁱⁱⁱ—C14—C11	126.5 (3)
C13—N1—Ni1	122.20 (15)	C14ⁱⁱⁱ—C14—H14	117.9 (18)
C19—N2—C15	116.78 (18)	C11—C14—H14	115.6 (18)
C19—N2—Ni1	116.73 (14)	N2—C15—C16	123.3 (2)
C15—N2—Ni1	126.49 (15)	N2—C15—H15	118.3
O6—N3—O5	123.4 (2)	C16—C15—H15	118.3
O6—N3—C6	118.2 (2)	C15—C16—C17	120.0 (2)
O5—N3—C6	118.3 (2)	C15—C16—H16	120.0
O1—C1—O2	121.02 (18)	C17—C16—H16	120.0
O1—C1—C2	118.64 (18)	C16—C17—C18	116.7 (2)
O2—C1—C2	120.31 (17)	C16—C17—C20	121.1 (2)
O1—C1—Ni1	58.36 (10)	C18—C17—C20	122.2 (2)
O2—C1—Ni1	62.86 (10)	C19—C18—C17	119.4 (2)
C2—C1—Ni1	173.30 (14)	C19—C18—H18	120.3
C3—C2—C7	119.69 (19)	C17—C18—H18	120.3
C3—C2—C1	121.18 (18)	N2—C19—C18	123.63 (19)
C7—C2—C1	119.07 (18)	N2—C19—H19	118.2
C2—C3—C4	120.61 (19)	C18—C19—H19	118.2
C2—C3—H3	119.7	C20^iv—C20—C17	124.9 (3)
C4—C3—H3	119.7	C20^iv—C20—H20	117.6
C5—C4—C3	119.60 (18)	C17—C20—H20	117.6
C5—C4—C8	119.83 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O4ⁱ	0.82	1.88	2.612 (2)	149
O7—H7B···O2^v	0.81 (1)	2.00 (1)	2.786 (2)	163 (3)

Symmetry codes: (i) x−1, y, z; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₃NO₆)(C₁₂H₁₀N₂)(H₂O)]
M_r	468.06
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3723 (6), 10.9947 (7), 11.1704 (8)
α, β, γ (°)	109.970 (1), 90.190 (1), 110.727 (1)
V (Å³)	1001.68 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.43 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.669, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	5380, 3580, 3332
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.089, 1.04
No. of reflections	3580
No. of parameters	287
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.29

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O3ⁱ	2.0326 (14)	Ni1—O7	2.0797 (15)
Ni1—N1	2.0417 (17)	Ni1—O1	2.1031 (14)
Ni1—N2	2.0777 (17)	Ni1—O2	2.2021 (14)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O4ⁱ	0.82	1.88	2.612 (2)	148.5
O7—H7B···O2ⁱⁱ	0.814 (10)	1.999 (13)	2.786 (2)	163 (3)

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

Acknowledgements

The project was supported by the Natural Science Foundation of Zhejiang Province, China (No. Y407091).

References

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