Aqua­bis(but-2-enoato-κO)(di-2-pyridyl­amine-κ2N,N′)nickel(II)

Yu, J.; Zhang, L.

doi:10.1107/S1600536807049100

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Aquabis(but-2-enoato-κO)(di-2-pyridylamine-κ²N,N′)nickel(II)

J. Yu and L. Zhang

In the title complex, [Ni(C₄H₅O₂)₂(C₁₀H₉N₃)(H₂O)], the Ni atom adopts a square-pyramidal NiO₃N₂ geometry, with the water molecule at the apical position and N₂O₂ donors in the basal plane. A network of O—H

O and N—H

O hydrogen bonds helps to establish the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049100/hb2571sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049100/hb2571Isup2.hkl Contains datablock I

CCDC reference: 669122

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.037
wR factor = 0.086
Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         18
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.36 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       5.78 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1      ..       5.82 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT245_ALERT_2_C U(iso) H21     Smaller than U(eq) O5      by ...       0.02 AngSq
PLAT351_ALERT_3_C Long    C-H Bond (0.96A)   C18    -   H18    ...       1.13 Ang.

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       1.94
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The molecular title complex, (I), complements related materials (Yang et al., 1997).

As shown in Fig. 1, the Ni(II) ion in (I) is coordinated by two N atoms of one chelating dipyridin-2-ylamine ligand, two O atoms of monodentate crotonictate anions and one O atom of a water molecule, forming a square-pyramidal coordination environment (Table 1). The N atoms occupy sites in the basal plane and the water molecule occupies the apical site.

A network of O—H···O and N—H···O hydrogen bonds helps to stabilize the packing (Table 2).

Related literature top

For background, see: Yang et al. (1997).

Experimental top

Dipyridin-2-ylamine (0.031 g, 0.016 mmol), crotonictic acid (0.028 g, 0.032 mmol), Ni(CH₃COO)₂ (0.18 g, 0.018 mmol) and NaOH (0.048 g, 0.12 mmol), were added to a mixed solvent of ethanol and acetonitrile. The mixture was heated for five hours under reflux with stirring. The resultant filtrate was infiltrated with diethyl ether in a closed vessel, and green blocks of (I) grew after one week.

Structure description top

The molecular title complex, (I), complements related materials (Yang et al., 1997).

A network of O—H···O and N—H···O hydrogen bonds helps to stabilize the packing (Table 2).

For background, see: Yang et al. (1997).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms).

Aquabis(but-2-enoato-κO)(di-2-pyridylamine-κ²N,N')nickel(II) top

Crystal data top

[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)(H₂O)]	F(000) = 872
M_r = 418.09	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3448 reflections
a = 7.1113 (7) Å	θ = 1.8–25.2°
b = 16.8303 (15) Å	µ = 1.05 mm⁻¹
c = 15.9850 (14) Å	T = 298 K
β = 91.291 (2)°	Block, green
V = 1912.7 (3) Å³	0.28 × 0.20 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3448 independent reflections
Radiation source: fine-focus sealed tube	2714 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
φ and ω scans	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→8
T_min = 0.758, T_max = 0.842	k = −20→20
9697 measured reflections	l = −17→19

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ²(F_o²) + (0.0445P)² + 0.001P] where P = (F_o² + 2F_c²)/3
3448 reflections	(Δ/σ)_max = 0.001
328 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)(H₂O)]	V = 1912.7 (3) Å³
M_r = 418.09	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1113 (7) Å	µ = 1.05 mm⁻¹
b = 16.8303 (15) Å	T = 298 K
c = 15.9850 (14) Å	0.28 × 0.20 × 0.17 mm
β = 91.291 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3448 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2714 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.842	R_int = 0.064
9697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	4 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.29 e Å⁻³
3448 reflections	Δρ_min = −0.33 e Å⁻³
328 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	0.19266 (4)	0.572833 (16)	0.669656 (17)	0.04340 (13)
O1	0.0960 (3)	0.68412 (10)	0.67000 (11)	0.0608 (5)
O2	−0.1803 (3)	0.62915 (11)	0.64370 (12)	0.0671 (5)
O3	0.0968 (3)	0.56323 (11)	0.78220 (12)	0.0723 (6)
O4	0.3460 (4)	0.59215 (14)	0.86344 (14)	0.0888 (7)
O5	0.4813 (4)	0.6002 (2)	0.71520 (16)	0.1188 (10)
N1	0.2755 (3)	0.58874 (10)	0.55233 (12)	0.0433 (5)
N2	0.2024 (3)	0.45996 (11)	0.50416 (12)	0.0449 (5)
N3	0.1835 (3)	0.45412 (12)	0.65126 (12)	0.0468 (5)
C1	0.3433 (4)	0.66180 (14)	0.53393 (17)	0.0514 (6)
C2	0.3911 (4)	0.68475 (16)	0.45623 (17)	0.0563 (7)
C3	0.3701 (4)	0.63070 (15)	0.39151 (17)	0.0560 (7)
C4	0.3075 (4)	0.55611 (15)	0.40780 (16)	0.0495 (6)
C5	0.2626 (3)	0.53616 (13)	0.48997 (14)	0.0399 (5)
C6	0.1751 (3)	0.41812 (12)	0.57651 (15)	0.0427 (6)
C7	0.1412 (4)	0.33687 (14)	0.56819 (18)	0.0536 (7)
C8	0.1230 (4)	0.29112 (17)	0.6374 (2)	0.0666 (8)
C9	0.1385 (5)	0.32646 (18)	0.7143 (2)	0.0741 (9)
C10	0.1671 (5)	0.40643 (17)	0.71917 (18)	0.0658 (8)
C11	−0.0792 (4)	0.68798 (15)	0.65862 (15)	0.0538 (6)
C12	−0.1703 (5)	0.76715 (19)	0.6610 (2)	0.0725 (9)
C13	−0.0853 (6)	0.83326 (18)	0.65710 (19)	0.0694 (8)
C14	−0.1754 (8)	0.9141 (2)	0.6553 (3)	0.0914 (12)
C15	0.1761 (5)	0.58259 (14)	0.85134 (18)	0.0604 (8)
C16	0.0516 (6)	0.59262 (17)	0.9241 (2)	0.0715 (9)
C17	−0.1283 (6)	0.59352 (17)	0.9198 (2)	0.0746 (9)
C18	−0.2552 (8)	0.6050 (3)	0.9942 (3)	0.1003 (13)
H9	0.195 (3)	0.4304 (11)	0.4590 (11)	0.044 (7)*
H1	0.356 (3)	0.6974 (14)	0.5834 (16)	0.060 (7)*
H4	0.292 (4)	0.5178 (16)	0.3622 (17)	0.070 (8)*
H3	0.398 (4)	0.6468 (13)	0.3352 (15)	0.054 (7)*
H19	−0.161 (5)	0.6191 (18)	1.047 (2)	0.092 (11)*
H6	0.098 (4)	0.2320 (16)	0.6302 (15)	0.068 (8)*
H2	0.437 (3)	0.7340 (15)	0.4474 (15)	0.056 (7)*
H5	0.130 (4)	0.3151 (15)	0.5107 (16)	0.062 (8)*
H15	0.100 (5)	0.6118 (19)	0.986 (2)	0.104 (11)*
H14	−0.320 (7)	0.912 (2)	0.663 (3)	0.14 (2)*
H18	−0.349 (6)	0.658 (2)	0.982 (2)	0.148 (16)*
H12	−0.149 (6)	0.940 (2)	0.602 (3)	0.133 (16)*
H8	0.179 (5)	0.4376 (17)	0.777 (2)	0.090 (10)*
H7	0.138 (4)	0.3000 (17)	0.7626 (18)	0.077 (9)*
H21	0.5918 (19)	0.610 (2)	0.6968 (19)	0.098 (11)*
H20	0.467 (6)	0.604 (2)	0.7683 (4)	0.117 (14)*
H10	−0.304 (6)	0.774 (3)	0.656 (2)	0.144 (17)*
H11	0.051 (6)	0.824 (2)	0.658 (2)	0.125 (15)*
H16	−0.186 (6)	0.587 (2)	0.864 (3)	0.142 (17)*
H17	−0.315 (6)	0.560 (2)	1.012 (3)	0.133 (17)*
H13	−0.120 (5)	0.947 (2)	0.700 (2)	0.113 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0463 (2)	0.03944 (18)	0.0448 (2)	−0.00627 (13)	0.00914 (14)	−0.00722 (12)
O1	0.0586 (12)	0.0435 (10)	0.0810 (13)	−0.0096 (9)	0.0216 (10)	−0.0161 (8)
O2	0.0676 (13)	0.0583 (11)	0.0758 (13)	−0.0152 (10)	0.0092 (10)	−0.0227 (9)
O3	0.0816 (15)	0.0798 (14)	0.0563 (12)	−0.0182 (11)	0.0211 (11)	−0.0110 (10)
O4	0.0887 (18)	0.1121 (19)	0.0657 (13)	0.0090 (15)	0.0046 (13)	−0.0040 (12)
O5	0.0608 (16)	0.232 (3)	0.0634 (16)	−0.0454 (19)	0.0058 (13)	−0.0179 (18)
N1	0.0430 (12)	0.0356 (10)	0.0515 (12)	−0.0028 (8)	0.0071 (9)	−0.0044 (8)
N2	0.0556 (13)	0.0323 (10)	0.0469 (12)	−0.0020 (9)	0.0042 (10)	−0.0058 (9)
N3	0.0493 (13)	0.0411 (10)	0.0500 (12)	0.0018 (9)	0.0034 (10)	0.0044 (9)
C1	0.0549 (16)	0.0387 (13)	0.0608 (16)	−0.0069 (12)	0.0108 (13)	−0.0050 (12)
C2	0.0583 (17)	0.0379 (14)	0.0734 (19)	−0.0023 (13)	0.0145 (14)	0.0062 (13)
C3	0.0602 (17)	0.0517 (16)	0.0567 (16)	0.0042 (13)	0.0138 (14)	0.0119 (13)
C4	0.0556 (16)	0.0455 (15)	0.0477 (15)	0.0031 (12)	0.0064 (12)	−0.0032 (12)
C5	0.0356 (12)	0.0325 (11)	0.0518 (14)	0.0026 (10)	0.0043 (10)	−0.0008 (10)
C6	0.0366 (13)	0.0358 (12)	0.0559 (15)	0.0004 (10)	0.0039 (11)	0.0022 (11)
C7	0.0565 (17)	0.0365 (13)	0.0679 (18)	−0.0009 (12)	0.0037 (14)	−0.0009 (12)
C8	0.0668 (19)	0.0420 (16)	0.091 (2)	0.0006 (14)	0.0043 (16)	0.0139 (15)
C9	0.093 (3)	0.0577 (19)	0.072 (2)	−0.0030 (16)	0.0045 (18)	0.0257 (17)
C10	0.084 (2)	0.0581 (17)	0.0552 (17)	−0.0019 (15)	0.0033 (15)	0.0114 (14)
C11	0.0607 (18)	0.0491 (15)	0.0523 (15)	−0.0026 (14)	0.0159 (13)	−0.0137 (12)
C12	0.068 (2)	0.0622 (19)	0.088 (2)	0.0017 (17)	0.0144 (18)	−0.0167 (16)
C13	0.088 (3)	0.0544 (18)	0.0661 (19)	0.0018 (18)	0.0069 (17)	−0.0039 (14)
C14	0.127 (4)	0.056 (2)	0.092 (3)	0.021 (2)	0.007 (3)	0.003 (2)
C15	0.089 (2)	0.0418 (15)	0.0513 (17)	0.0103 (15)	0.0145 (16)	0.0011 (12)
C16	0.098 (3)	0.0581 (18)	0.0585 (19)	0.0079 (18)	0.0128 (18)	−0.0005 (14)
C17	0.095 (3)	0.0511 (17)	0.079 (2)	−0.0052 (18)	0.021 (2)	−0.0035 (15)
C18	0.117 (4)	0.088 (3)	0.098 (3)	−0.006 (3)	0.050 (3)	−0.010 (2)

Geometric parameters (Å, º) top

Ni1—N1	1.9965 (19)	C4—H4	0.98 (3)
Ni1—N3	2.020 (2)	C6—C7	1.394 (3)
Ni1—O3	1.9449 (19)	C7—C8	1.357 (4)
Ni1—O1	1.9953 (17)	C7—H5	0.99 (3)
Ni1—O5	2.211 (3)	C8—C9	1.367 (4)
O1—C11	1.257 (3)	C8—H6	1.02 (3)
O2—C11	1.243 (3)	C9—C10	1.363 (4)
O3—C15	1.272 (4)	C9—H7	0.89 (3)
O4—C15	1.230 (4)	C10—H8	1.06 (3)
O5—H21	0.864 (18)	C11—C12	1.482 (4)
O5—H20	0.860 (9)	C12—C13	1.268 (4)
N1—C5	1.335 (3)	C12—H10	0.96 (4)
N1—C1	1.355 (3)	C13—C14	1.505 (5)
N2—C6	1.372 (3)	C13—H11	0.99 (4)
N2—C5	1.373 (3)	C14—H14	1.04 (5)
N2—H9	0.877 (15)	C14—H12	0.97 (4)
N3—C6	1.340 (3)	C14—H13	0.98 (4)
N3—C10	1.357 (3)	C15—C16	1.486 (4)
C1—C2	1.351 (4)	C16—C17	1.280 (5)
C1—H1	0.99 (3)	C16—H15	1.08 (3)
C2—C3	1.383 (4)	C17—C18	1.522 (5)
C2—H2	0.90 (2)	C17—H16	0.98 (4)
C3—C4	1.359 (3)	C18—H19	1.09 (3)
C3—H3	0.97 (2)	C18—H18	1.13 (4)
C4—C5	1.400 (3)	C18—H17	0.92 (4)

O3—Ni1—O1	86.99 (8)	C8—C7—C6	119.9 (3)
O3—Ni1—N1	175.62 (8)	C8—C7—H5	122.6 (15)
O1—Ni1—N1	89.18 (7)	C6—C7—H5	117.5 (15)
O3—Ni1—N3	92.38 (8)	C7—C8—C9	118.6 (3)
O1—Ni1—N3	156.74 (8)	C7—C8—H6	118.9 (14)
N1—Ni1—N3	90.30 (7)	C9—C8—H6	122.5 (14)
O3—Ni1—O5	93.14 (9)	C8—C9—C10	119.3 (3)
O1—Ni1—O5	96.93 (12)	C8—C9—H7	124.0 (19)
N1—Ni1—O5	89.42 (9)	C10—C9—H7	116.6 (19)
N3—Ni1—O5	106.32 (11)	N3—C10—C9	123.6 (3)
C11—O1—Ni1	112.88 (16)	N3—C10—H8	113.4 (16)
C15—O3—Ni1	128.7 (2)	C9—C10—H8	123.0 (16)
Ni1—O5—H21	141 (2)	O2—C11—O1	123.6 (2)
Ni1—O5—H20	102 (3)	O2—C11—C12	118.0 (3)
H21—O5—H20	117 (3)	O1—C11—C12	118.4 (3)
C5—N1—C1	117.3 (2)	C13—C12—C11	125.4 (3)
C5—N1—Ni1	126.58 (15)	C13—C12—H10	111 (3)
C1—N1—Ni1	116.07 (15)	C11—C12—H10	123 (3)
C6—N2—C5	132.0 (2)	C12—C13—C14	126.3 (4)
C6—N2—H9	113.3 (14)	C12—C13—H11	109 (2)
C5—N2—H9	114.1 (14)	C14—C13—H11	125 (2)
C6—N3—C10	116.3 (2)	C13—C14—H14	113 (2)
C6—N3—Ni1	125.28 (16)	C13—C14—H12	109 (2)
C10—N3—Ni1	118.14 (19)	H14—C14—H12	110 (3)
C2—C1—N1	123.8 (2)	C13—C14—H13	109 (2)
C2—C1—H1	122.5 (14)	H14—C14—H13	108 (3)
N1—C1—H1	113.7 (14)	H12—C14—H13	108 (3)
C1—C2—C3	118.3 (2)	O4—C15—O3	125.8 (3)
C1—C2—H2	120.4 (16)	O4—C15—C16	117.5 (3)
C3—C2—H2	121.3 (16)	O3—C15—C16	116.7 (3)
C4—C3—C2	119.6 (2)	C17—C16—C15	124.8 (3)
C4—C3—H3	121.0 (14)	C17—C16—H15	109.8 (18)
C2—C3—H3	119.4 (14)	C15—C16—H15	124.3 (19)
C3—C4—C5	118.9 (2)	C16—C17—C18	124.7 (4)
C3—C4—H4	119.8 (16)	C16—C17—H16	117 (3)
C5—C4—H4	121.2 (16)	C18—C17—H16	119 (3)
N1—C5—N2	120.8 (2)	C17—C18—H19	105.4 (18)
N1—C5—C4	121.9 (2)	C17—C18—H18	109 (2)
N2—C5—C4	117.2 (2)	H19—C18—H18	108 (3)
N3—C6—N2	121.0 (2)	C17—C18—H17	116 (3)
N3—C6—C7	122.2 (2)	H19—C18—H17	103 (3)
N2—C6—C7	116.8 (2)	H18—C18—H17	115 (4)

O3—Ni1—O1—C11	−76.91 (18)	Ni1—N1—C5—C4	173.39 (18)
N1—Ni1—O1—C11	100.97 (18)	C6—N2—C5—N1	−11.9 (4)
N3—Ni1—O1—C11	12.1 (3)	C6—N2—C5—C4	168.7 (2)
O5—Ni1—O1—C11	−169.71 (18)	C3—C4—C5—N1	1.5 (4)
O1—Ni1—O3—C15	−85.3 (2)	C3—C4—C5—N2	−179.1 (2)
O5—Ni1—O3—C15	11.5 (2)	C10—N3—C6—N2	−175.7 (2)
O1—Ni1—N1—C5	−140.0 (2)	Ni1—N3—C6—N2	10.6 (3)
N3—Ni1—N1—C5	16.7 (2)	C10—N3—C6—C7	3.4 (4)
O5—Ni1—N1—C5	123.1 (2)	Ni1—N3—C6—C7	−170.30 (19)
O1—Ni1—N1—C1	36.66 (19)	C5—N2—C6—N3	9.3 (4)
N3—Ni1—N1—C1	−166.59 (19)	C5—N2—C6—C7	−169.9 (2)
O5—Ni1—N1—C1	−60.3 (2)	N3—C6—C7—C8	−2.7 (4)
O3—Ni1—N3—C6	157.6 (2)	N2—C6—C7—C8	176.5 (3)
O1—Ni1—N3—C6	69.7 (3)	C6—C7—C8—C9	0.0 (5)
N1—Ni1—N3—C6	−18.9 (2)	C7—C8—C9—C10	1.6 (5)
O5—Ni1—N3—C6	−108.4 (2)	C6—N3—C10—C9	−1.7 (4)
O3—Ni1—N3—C10	−16.0 (2)	Ni1—N3—C10—C9	172.4 (3)
O1—Ni1—N3—C10	−103.9 (3)	C8—C9—C10—N3	−0.8 (5)
N1—Ni1—N3—C10	167.4 (2)	Ni1—O1—C11—O2	−4.1 (3)
O5—Ni1—N3—C10	78.0 (2)	Ni1—O1—C11—C12	177.52 (19)
C5—N1—C1—C2	2.6 (4)	O2—C11—C12—C13	−163.8 (3)
Ni1—N1—C1—C2	−174.4 (2)	O1—C11—C12—C13	14.7 (5)
N1—C1—C2—C3	−0.1 (4)	C11—C12—C13—C14	176.9 (3)
C1—C2—C3—C4	−1.8 (4)	Ni1—O3—C15—O4	−20.2 (4)
C2—C3—C4—C5	1.1 (4)	Ni1—O3—C15—C16	161.29 (19)
C1—N1—C5—N2	177.4 (2)	O4—C15—C16—C17	171.7 (3)
Ni1—N1—C5—N2	−5.9 (3)	O3—C15—C16—C17	−9.6 (4)
C1—N1—C5—C4	−3.2 (4)	C15—C16—C17—C18	−179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H20···O4	0.86 (1)	1.78 (2)	2.581 (3)	155 (4)
O5—H21···O2ⁱ	0.86 (2)	1.87 (2)	2.731 (3)	173 (3)
N2—H9···O2ⁱⁱ	0.88 (2)	1.93 (2)	2.801 (3)	177 (2)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₄H₅O₂)₂(C₁₀H₉N₃)(H₂O)]
M_r	418.09
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.1113 (7), 16.8303 (15), 15.9850 (14)
β (°)	91.291 (2)
V (Å³)	1912.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.28 × 0.20 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.758, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	9697, 3448, 2714
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 0.91
No. of reflections	3448
No. of parameters	328
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004).

Selected bond lengths (Å) top

Ni1—N1	1.9965 (19)	Ni1—O1	1.9953 (17)
Ni1—N3	2.020 (2)	Ni1—O5	2.211 (3)
Ni1—O3	1.9449 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H20···O4	0.860 (9)	1.776 (17)	2.581 (3)	155 (4)
O5—H21···O2ⁱ	0.861 (18)	1.874 (19)	2.731 (3)	173 (3)
N2—H9···O2ⁱⁱ	0.877 (15)	1.925 (16)	2.801 (3)	177 (2)

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

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