(Di-2-pyridylamine-κ2N1,N1′)bis­(methacrylato-κO)nickel(II) sesqui­hydrate

Meng, F.; Xia, L.; Zhu, X.

doi:10.1107/S1600536808009008

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m640

doi:10.1107/S1600536808009008

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(Di-2-pyridylamine-κ²N¹,N^1′)bis(methacrylato-κO)nickel(II) sesquihydrate

Fankun Meng,^a ^* Lili Xia ^b and Xiaoxiao Zhu ^c

^aDepartment of Chemistry and Chemical Engineering, Daqing Normal University, 163712 Daqing, Heilongjiang, People's Republic of China, ^bThe No. 4 Middle School of Liaocheng, 252000 Liaocheng, Shandong, People's Republic of China, and ^cTaishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: klsz79@163.com

(Received 25 February 2008; accepted 3 April 2008; online 10 April 2008)

In the title mononuclear complex, [Ni(C₄H₅O₂)₂(C₁₀H₉N₃)]·1.5H₂O, the Ni^II ion is in a distorted square-planar coordination environment, formed by two O atoms from two methacrylate ligands and two N atoms from a bis-chelating dipyridylamine ligand. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link complex molecules and water molecules into one-dimensional chains.

Related literature

For the Cu analog of the title compound, see: Liu, et al. (2006 ). For related literature, see: Carabias-Martínez et al. (2006 ); Matsui et al. (1997 ); Wang et al. (1997 ); Wu et al. (2002 ).

Experimental

Crystal data

[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)]·1.5H₂O
M_r = 427.10
Monoclinic, P 2₁ /n
a = 8.3686 (9) Å
b = 15.7235 (16) Å
c = 15.5396 (17) Å
β = 101.483 (2)°
V = 2003.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 (2) K
0.29 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.740, T_max = 0.872
9960 measured reflections
3512 independent reflections
2720 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.084
S = 1.00
3512 reflections
311 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O3	1.9669 (18)
Ni1—N2	1.980 (2)
Ni1—N1	1.9801 (18)
Ni1—O1	1.9843 (17)

O3—Ni1—N2	93.16 (8)
O3—Ni1—N1	154.32 (8)
N2—Ni1—N1	92.47 (8)
O3—Ni1—O1	92.24 (8)
N2—Ni1—O1	153.74 (8)
N1—Ni1—O1	93.70 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯O3ⁱ	0.85	2.31	3.030	143
N3—H19⋯O5ⁱⁱ	0.86	1.99	2.837 (3)	170
O5—H20⋯O2	0.96 (3)	1.75 (3)	2.698 (3)	169 (2)
O5—H21⋯O4ⁱⁱⁱ	0.92 (3)	1.88 (3)	2.789 (3)	169 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) x-1, y, z.

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); 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/S1600536808009008/lh2600sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009008/lh2600Isup2.hkl

checkCIF report

Comment top

Methacrylic acid and its derivatives are biologically active compounds which are widely used as herbicides and plantgrowth substances (Matsui et al., 1997; Carabias-Martínez et al., 2006). Due to their versatile bonding modes with metal ions, they have also been used in the synthesis of mononuclear or multi-nuclear compounds (Wang et al., 1997; Wu et al., 2002). In order to develop some new topological structures, the reaction system of a nickel(II)chloride with methacrylic acid and dipyridin-2-ylamine has been explored.

Herein we report the structure of the title compound (Fig. 1). It is isostructural with the Cu analog (Liu et al., 2006) but we have located and refined an addtional half of a water solvent molecule. The Ni^II ion is in a distorted square-planar coordination environment, formed by two O atoms from two methacrylate ligands and two N atoms from a bis-chelataing dipyridin-2-ylamine ligand. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds link complex molecules and water molecules into a to form one-dimensional chains (Fig. 2).

Related literature top

For the Cu analog of the title compound, see: Liu, et al. (2006). For related literature, see: Carabias-Martínez et al. (2006); Matsui et al. (1997); Wang et al. (1997); Wu et al. (2002).

Experimental top

Methacrylic acid and dipyridin-2-ylamine are commercially available, and they were used without further purification. The reaction was carried out under an air atmoshpere. Methacrylic acid (2 mmol), dipyridin-2-ylamine (1 mmol) and nickel(II)chloride (1 mmol) were added to water and the mixture was stirred for 4 h at 323 K. After cooling to room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum, and the solid residue was recrystallized from ethanol to form yellow crystals which were suitable for X-Ray diffraction study. Yield, 78%. m.p. 547 K. Analysis, calculated for C₁₈H₂₂N₃NiO_5.50: C 50.62, H 5.19, N 9.84; found: C 50.38, H 5.43, N 9.52. The elemental analyses were performed with a Perkine Elemer PE2400II instrument.

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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 the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted.
	Fig. 2. The one-dimensional structure formed via intermolecular O—H···O and N—H···O hydrogen bonds. Hydrogen bonds are shown as red lines.

(Di-2-pyridylamine-κ²N¹,N^1')bis(methacrylato-κO)nickel(II) sesquihydrate top

Crystal data top

[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)]·1.5H₂O	F(000) = 892
M_r = 427.10	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4631 reflections
a = 8.3686 (9) Å	θ = 1.9–28.3°
b = 15.7235 (16) Å	µ = 1.00 mm⁻¹
c = 15.5396 (17) Å	T = 293 K
β = 101.483 (2)°	Block, blue
V = 2003.8 (4) Å³	0.29 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	2720 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.740, T_max = 0.872	k = −18→17
9960 measured reflections	l = −15→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.03P)²] where P = (F_o² + 2F_c²)/3
3512 reflections	(Δ/σ)_max = 0.013
311 parameters	Δρ_max = 0.32 e Å⁻³
13 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)]·1.5H₂O	V = 2003.8 (4) Å³
M_r = 427.10	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3686 (9) Å	µ = 1.00 mm⁻¹
b = 15.7235 (16) Å	T = 293 K
c = 15.5396 (17) Å	0.29 × 0.22 × 0.18 mm
β = 101.483 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3512 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2720 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.872	R_int = 0.077
9960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	13 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.32 e Å⁻³
3512 reflections	Δρ_min = −0.24 e Å⁻³
311 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)
Ni1	0.71669 (3)	0.166235 (18)	0.635377 (19)	0.05233 (13)
O1	0.6953 (2)	0.18663 (11)	0.75859 (11)	0.0676 (5)
O2	0.4520 (2)	0.16405 (13)	0.68304 (14)	0.0869 (6)
O3	0.6959 (2)	0.28811 (11)	0.60684 (13)	0.0744 (5)
O4	0.9584 (2)	0.26650 (12)	0.62783 (14)	0.0866 (6)
O5	0.1555 (3)	0.13886 (13)	0.58041 (14)	0.0871 (6)
O6	0.1576 (18)	0.8401 (6)	0.9099 (9)	0.365 (9)	0.50
H6A	0.2379	0.8070	0.9103	0.437*	0.50
H6B	0.0724	0.8139	0.8846	0.437*	0.50
N1	0.8388 (2)	0.05866 (11)	0.66380 (12)	0.0554 (5)
N2	0.6341 (2)	0.13116 (12)	0.51218 (13)	0.0555 (5)
N3	0.7837 (2)	0.00393 (12)	0.51996 (13)	0.0599 (5)
H19	0.8113	−0.0357	0.4877	0.072*
C1	0.9209 (4)	0.0486 (2)	0.74736 (19)	0.0786 (8)
C2	1.0198 (4)	−0.0173 (2)	0.7755 (2)	0.0922 (10)
C3	1.0384 (4)	−0.0799 (2)	0.7157 (2)	0.0857 (9)
C4	0.9597 (3)	−0.07131 (17)	0.63130 (19)	0.0682 (7)
C5	0.8605 (3)	−0.00130 (14)	0.60641 (16)	0.0530 (6)
C6	0.6718 (3)	0.05967 (14)	0.47463 (15)	0.0514 (5)
C7	0.5986 (3)	0.03930 (18)	0.38840 (17)	0.0659 (7)
C8	0.4874 (4)	0.0926 (2)	0.34175 (19)	0.0745 (8)
C9	0.4470 (4)	0.1665 (2)	0.38006 (19)	0.0724 (8)
C10	0.5214 (3)	0.18320 (18)	0.4632 (2)	0.0693 (7)
C11	0.5437 (3)	0.18002 (14)	0.75381 (19)	0.0612 (7)
C12	0.4763 (4)	0.18975 (16)	0.8346 (2)	0.0745 (8)
C13	0.5788 (7)	0.1974 (2)	0.9112 (3)	0.1023 (12)
C14	0.3001 (5)	0.1899 (3)	0.8252 (3)	0.1299 (14)
H13	0.2721	0.2052	0.8801	0.195*
H11	0.2583	0.1342	0.8081	0.195*
H12	0.2534	0.2304	0.7810	0.195*
C15	0.8403 (4)	0.31425 (16)	0.60955 (16)	0.0606 (6)
C16	0.8616 (4)	0.40609 (18)	0.58992 (18)	0.0745 (7)
C17	1.0179 (7)	0.4399 (3)	0.6099 (3)	0.1124 (13)
C18	0.7233 (5)	0.4528 (2)	0.5499 (3)	0.1287 (14)
H17	0.7563	0.5083	0.5343	0.193*
H18	0.6504	0.4584	0.5901	0.193*
H16	0.6688	0.4237	0.4980	0.193*
H1	0.913 (3)	0.0917 (18)	0.7842 (18)	0.083 (9)*
H2	1.086 (3)	−0.0193 (18)	0.8329 (14)	0.099 (10)*
H3	1.108 (4)	−0.131 (2)	0.733 (2)	0.117 (11)*
H4	0.964 (3)	−0.1118 (14)	0.5870 (14)	0.066 (7)*
H5	0.630 (2)	−0.0103 (11)	0.3650 (14)	0.058 (7)*
H6	0.430 (3)	0.0750 (19)	0.281 (2)	0.106 (10)*
H7	0.373 (3)	0.2059 (16)	0.3503 (17)	0.076 (8)*
H8	0.495 (3)	0.2368 (17)	0.4916 (17)	0.084 (8)*
H9	0.690 (2)	0.187 (2)	0.919 (2)	0.118 (16)*
H10	0.523 (5)	0.207 (2)	0.958 (3)	0.153 (15)*
H14	1.099 (4)	0.403 (2)	0.633 (2)	0.133 (17)*
H15	1.031 (4)	0.4937 (15)	0.592 (2)	0.134 (14)*
H20	0.257 (3)	0.1554 (17)	0.6173 (18)	0.099 (11)*
H21	0.082 (4)	0.1753 (18)	0.598 (2)	0.128 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0512 (2)	0.0530 (2)	0.0534 (2)	0.00317 (13)	0.01212 (15)	−0.00762 (14)
O1	0.0629 (12)	0.0792 (12)	0.0624 (11)	−0.0013 (9)	0.0162 (9)	−0.0175 (9)
O2	0.0608 (12)	0.1171 (17)	0.0832 (14)	−0.0144 (11)	0.0152 (11)	−0.0286 (12)
O3	0.0689 (12)	0.0613 (11)	0.0941 (13)	0.0041 (9)	0.0191 (10)	−0.0042 (10)
O4	0.0766 (13)	0.0790 (13)	0.1072 (16)	0.0182 (10)	0.0254 (12)	0.0057 (11)
O5	0.0704 (13)	0.0955 (14)	0.0905 (15)	0.0182 (11)	0.0041 (12)	−0.0320 (12)
O6	0.410 (19)	0.215 (11)	0.395 (19)	−0.049 (10)	−0.096 (16)	0.069 (10)
N1	0.0556 (12)	0.0580 (12)	0.0519 (11)	0.0019 (9)	0.0089 (10)	−0.0038 (9)
N2	0.0527 (12)	0.0598 (12)	0.0546 (12)	0.0037 (10)	0.0121 (10)	0.0011 (10)
N3	0.0686 (13)	0.0582 (12)	0.0528 (12)	0.0107 (10)	0.0121 (10)	−0.0075 (10)
C1	0.084 (2)	0.086 (2)	0.0597 (18)	0.0167 (17)	−0.0003 (15)	−0.0109 (16)
C2	0.096 (2)	0.105 (2)	0.0633 (19)	0.030 (2)	−0.0122 (18)	−0.0020 (18)
C3	0.088 (2)	0.078 (2)	0.084 (2)	0.0213 (17)	−0.0027 (18)	0.0054 (18)
C4	0.0713 (17)	0.0595 (16)	0.0708 (18)	0.0055 (13)	0.0066 (15)	−0.0046 (14)
C5	0.0500 (13)	0.0518 (13)	0.0579 (15)	−0.0019 (11)	0.0125 (11)	0.0015 (12)
C6	0.0490 (13)	0.0567 (14)	0.0504 (13)	−0.0009 (11)	0.0146 (11)	0.0006 (11)
C7	0.0716 (17)	0.0738 (18)	0.0531 (16)	0.0097 (14)	0.0147 (14)	−0.0050 (14)
C8	0.0739 (19)	0.098 (2)	0.0507 (16)	−0.0005 (17)	0.0103 (15)	0.0084 (16)
C9	0.0701 (19)	0.081 (2)	0.0639 (18)	0.0116 (16)	0.0085 (15)	0.0116 (16)
C10	0.0681 (18)	0.0674 (18)	0.0710 (19)	0.0138 (14)	0.0101 (15)	0.0034 (14)
C11	0.0621 (17)	0.0529 (15)	0.0728 (18)	−0.0060 (12)	0.0234 (15)	−0.0125 (12)
C12	0.104 (2)	0.0500 (14)	0.0812 (19)	−0.0052 (14)	0.0472 (18)	−0.0095 (14)
C13	0.155 (4)	0.084 (2)	0.081 (2)	−0.020 (3)	0.056 (3)	−0.0093 (19)
C14	0.119 (3)	0.144 (3)	0.153 (4)	0.010 (2)	0.089 (3)	0.005 (3)
C15	0.0705 (18)	0.0624 (16)	0.0520 (14)	0.0061 (14)	0.0193 (14)	−0.0061 (12)
C16	0.101 (2)	0.0637 (17)	0.0669 (17)	−0.0049 (15)	0.0361 (16)	−0.0069 (14)
C17	0.147 (4)	0.093 (3)	0.104 (3)	−0.034 (3)	0.044 (3)	0.000 (2)
C18	0.160 (3)	0.080 (2)	0.161 (4)	0.039 (2)	0.067 (3)	0.030 (2)

Geometric parameters (Å, º) top

Ni1—O3	1.9669 (18)	C4—H4	0.944 (16)
Ni1—N2	1.980 (2)	C6—C7	1.395 (3)
Ni1—N1	1.9801 (18)	C7—C8	1.351 (4)
Ni1—O1	1.9843 (17)	C7—H5	0.921 (15)
O1—C11	1.260 (3)	C8—C9	1.378 (4)
O2—C11	1.235 (3)	C8—H6	1.01 (3)
O3—C15	1.269 (3)	C9—C10	1.343 (4)
O4—C15	1.228 (3)	C9—H7	0.93 (3)
O5—H20	0.961 (18)	C10—H8	1.00 (3)
O5—H21	0.921 (18)	C11—C12	1.483 (4)
O6—H6A	0.8498	C12—C13	1.327 (5)
O6—H6B	0.8497	C12—C14	1.453 (4)
N1—C5	1.335 (3)	C13—H9	0.930 (18)
N1—C1	1.352 (3)	C13—H10	0.95 (4)
N2—C6	1.333 (3)	C14—H13	0.9600
N2—C10	1.361 (3)	C14—H11	0.9600
N3—C6	1.371 (3)	C14—H12	0.9600
N3—C5	1.371 (3)	C15—C16	1.494 (4)
N3—H19	0.8600	C16—C17	1.389 (5)
C1—C2	1.344 (4)	C16—C18	1.407 (4)
C1—H1	0.90 (3)	C17—H14	0.911 (18)
C2—C3	1.383 (4)	C17—H15	0.906 (19)
C2—H2	0.954 (18)	C18—H17	0.9600
C3—C4	1.353 (4)	C18—H18	0.9600
C3—H3	1.00 (3)	C18—H16	0.9600
C4—C5	1.387 (3)

O3—Ni1—N2	93.16 (8)	C7—C8—C9	119.6 (3)
O3—Ni1—N1	154.32 (8)	C7—C8—H6	118.8 (17)
N2—Ni1—N1	92.47 (8)	C9—C8—H6	121.5 (17)
O3—Ni1—O1	92.24 (8)	C10—C9—C8	118.3 (3)
N2—Ni1—O1	153.74 (8)	C10—C9—H7	118.8 (16)
N1—Ni1—O1	93.70 (7)	C8—C9—H7	122.9 (16)
C11—O1—Ni1	102.29 (16)	C9—C10—N2	123.9 (3)
C15—O3—Ni1	105.48 (16)	C9—C10—H8	119.4 (15)
H20—O5—H21	103 (3)	N2—C10—H8	116.7 (15)
H6A—O6—H6B	107.1	O2—C11—O1	120.6 (2)
C5—N1—C1	116.6 (2)	O2—C11—C12	120.0 (3)
C5—N1—Ni1	125.95 (16)	O1—C11—C12	119.3 (3)
C1—N1—Ni1	117.08 (18)	C13—C12—C14	123.5 (4)
C6—N2—C10	117.4 (2)	C13—C12—C11	118.8 (3)
C6—N2—Ni1	126.19 (16)	C14—C12—C11	117.7 (3)
C10—N2—Ni1	116.32 (18)	C12—C13—H9	124 (2)
C6—N3—C5	132.90 (19)	C12—C13—H10	112 (3)
C6—N3—H19	113.5	H9—C13—H10	124 (4)
C5—N3—H19	113.5	C12—C14—H13	109.5
C2—C1—N1	124.4 (3)	C12—C14—H11	109.5
C2—C1—H1	119.6 (17)	H13—C14—H11	109.5
N1—C1—H1	115.9 (18)	C12—C14—H12	109.5
C1—C2—C3	118.4 (3)	H13—C14—H12	109.5
C1—C2—H2	122.5 (18)	H11—C14—H12	109.5
C3—C2—H2	118.8 (17)	O4—C15—O3	121.8 (2)
C4—C3—C2	118.8 (3)	O4—C15—C16	121.0 (3)
C4—C3—H3	119 (2)	O3—C15—C16	117.2 (2)
C2—C3—H3	122 (2)	C17—C16—C18	123.6 (4)
C3—C4—C5	119.9 (3)	C17—C16—C15	118.1 (3)
C3—C4—H4	123.9 (15)	C18—C16—C15	118.3 (3)
C5—C4—H4	116.1 (15)	C16—C17—H14	116 (3)
N1—C5—N3	120.8 (2)	C16—C17—H15	117 (3)
N1—C5—C4	121.9 (2)	H14—C17—H15	126 (4)
N3—C5—C4	117.3 (2)	C16—C18—H17	109.5
N2—C6—N3	120.8 (2)	C16—C18—H18	109.5
N2—C6—C7	121.1 (2)	H17—C18—H18	109.5
N3—C6—C7	118.1 (2)	C16—C18—H16	109.5
C8—C7—C6	119.8 (3)	H17—C18—H16	109.5
C8—C7—H5	122.3 (14)	H18—C18—H16	109.5
C6—C7—H5	117.9 (14)

O3—Ni1—O1—C11	90.93 (15)	C6—N3—C5—C4	175.2 (2)
N2—Ni1—O1—C11	−10.8 (3)	C3—C4—C5—N1	−0.4 (4)
N1—Ni1—O1—C11	−114.07 (15)	C3—C4—C5—N3	−179.9 (3)
N2—Ni1—O3—C15	−105.33 (17)	C10—N2—C6—N3	−179.7 (2)
N1—Ni1—O3—C15	−2.9 (3)	Ni1—N2—C6—N3	−3.6 (3)
O1—Ni1—O3—C15	100.38 (17)	C10—N2—C6—C7	0.1 (3)
O3—Ni1—N1—C5	−94.3 (2)	Ni1—N2—C6—C7	176.25 (17)
N2—Ni1—N1—C5	8.28 (19)	C5—N3—C6—N2	9.6 (4)
O1—Ni1—N1—C5	162.74 (18)	C5—N3—C6—C7	−170.3 (2)
O3—Ni1—N1—C1	78.9 (3)	N2—C6—C7—C8	0.0 (4)
N2—Ni1—N1—C1	−178.6 (2)	N3—C6—C7—C8	179.8 (2)
O1—Ni1—N1—C1	−24.1 (2)	C6—C7—C8—C9	−0.3 (4)
O3—Ni1—N2—C6	151.52 (18)	C7—C8—C9—C10	0.5 (4)
N1—Ni1—N2—C6	−3.41 (19)	C8—C9—C10—N2	−0.4 (4)
O1—Ni1—N2—C6	−106.9 (2)	C6—N2—C10—C9	0.1 (4)
O3—Ni1—N2—C10	−32.28 (19)	Ni1—N2—C10—C9	−176.4 (2)
N1—Ni1—N2—C10	172.79 (18)	Ni1—O1—C11—O2	0.2 (3)
O1—Ni1—N2—C10	69.3 (3)	Ni1—O1—C11—C12	178.91 (18)
C5—N1—C1—C2	−0.7 (4)	O2—C11—C12—C13	172.6 (3)
Ni1—N1—C1—C2	−174.4 (3)	O1—C11—C12—C13	−6.1 (4)
N1—C1—C2—C3	−0.7 (5)	O2—C11—C12—C14	−7.1 (4)
C1—C2—C3—C4	1.6 (5)	O1—C11—C12—C14	174.2 (3)
C2—C3—C4—C5	−1.1 (5)	Ni1—O3—C15—O4	−0.5 (3)
C1—N1—C5—N3	−179.3 (2)	Ni1—O3—C15—C16	179.79 (18)
Ni1—N1—C5—N3	−6.1 (3)	O4—C15—C16—C17	−12.7 (4)
C1—N1—C5—C4	1.2 (4)	O3—C15—C16—C17	167.0 (3)
Ni1—N1—C5—C4	174.35 (18)	O4—C15—C16—C18	165.4 (3)
C6—N3—C5—N1	−4.3 (4)	O3—C15—C16—C18	−14.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O2ⁱ	0.85	2.57	3.172	129
O6—H6B···O3ⁱ	0.85	2.31	3.030	143
N3—H19···O5ⁱⁱ	0.86	1.99	2.837 (3)	170
O5—H20···O2	0.96 (3)	1.75 (3)	2.698 (3)	169 (2)
O5—H21···O4ⁱⁱⁱ	0.92 (3)	1.88 (3)	2.789 (3)	169 (3)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)]·1.5H₂O
M_r	427.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.3686 (9), 15.7235 (16), 15.5396 (17)
β (°)	101.483 (2)
V (Å³)	2003.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.29 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.740, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	9960, 3512, 2720
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.084, 1.00
No. of reflections	3512
No. of parameters	311
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O3	1.9669 (18)	Ni1—N1	1.9801 (18)
Ni1—N2	1.980 (2)	Ni1—O1	1.9843 (17)

O3—Ni1—N2	93.16 (8)	O3—Ni1—O1	92.24 (8)
O3—Ni1—N1	154.32 (8)	N2—Ni1—O1	153.74 (8)
N2—Ni1—N1	92.47 (8)	N1—Ni1—O1	93.70 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O3ⁱ	0.85	2.31	3.030	143
N3—H19···O5ⁱⁱ	0.86	1.99	2.837 (3)	170
O5—H20···O2	0.96 (3)	1.75 (3)	2.698 (3)	169 (2)
O5—H21···O4ⁱⁱⁱ	0.92 (3)	1.88 (3)	2.789 (3)	169 (3)

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

Acknowledgements

The authors thank the Postgraduate Foundation of Daqing Normal University for financial support.

References

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