Aqua(4,4-bi­pyridine)­phthalatonickel(II) trihydrate

Yang, S.-Y.; Long, L.-S.; Huang, R.-B.; Zheng, L.-S.; Ng, S.W.

doi:10.1107/S1600536803013448

Aqua(4,4-bipyridine)phthalatonickel(II) trihydrate

S.-Y. Yang, L.-S. Long, R.-B. Huang, L.-S. Zheng and S. W. Ng

The (H₂O)(C₁₀H₈N₂)Ni(C₈H₄O₄) portion of the title compound, [Ni(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·3H₂O, adopts a layer architecture in which the dianionic entity chelates to the Ni atom [Ni-O = 2.053 (5) and 2.056 (4) Å, and O-Ni-O = 91.5 (2)°]. The two chelating O atoms, a water molecule [Ni-O = 2.083 (5) Å], the carboxyl O atom from an adjacent dianion, and the N atoms of two 4,4'-bipyridine heterocycles comprise the octahedron around the Ni atom. Adjacent layers are linked into a network motif by hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013448/cv6200sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013448/cv6200Isup2.hkl Contains datablock I

CCDC reference: 217387

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.060
wR factor = 0.153
Data-to-parameter ratio = 11.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



ABSTM_02  Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
          Tmin and Tmax reported:      0.455     0.939
          Tmin' and Tmax expected:      0.703     0.938
          RR' =      0.646
          Please check that your absorption correction is appropriate.

PLAT_420  Alert B D-H Without Acceptor       O2W    -   H2W1   ...          ?

PLAT_420  Alert B D-H Without Acceptor       O3W    -   H3W2   ...          ?

PLAT_420  Alert B D-H Without Acceptor       O4W    -   H4W2   ...          ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.00
         From the CIF: _reflns_number_total               2936
         Count of symmetry unique reflns         2947
         Completeness (_total/calc)             99.63%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 4 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

In our studies on the complexes of transition metal benzenedicarboxylates, we have documented the 4,4'-bipyridine adduct of nickel(II) terephthalate (Yang et al., 2003). The use of phthalic anhydride as the reagent in place of terephthalic acid in the synthesis afforded the analogous nickel phthalate, but the compound crystallizes with four water molecules, one of which is coordinated to the Ni atom (Fig. 1 and Table 1). In the (H₂O)(C₁₀H₈N₂)Ni(C₈H₄O₄) unit, the phthalate dianion chelates to the Ni atom [Ni—O = 2.053 (5) and 2.056 (4) Å, and O—Ni—O = 91.5 (2)°]. The two chelating O atoms, a water molecule [Ni—O = 2.083 (5) Å], the carboxyl O atom from an adjacent dianion, and the N atoms of two 4,4'-bipyridine heterocycles comprise the octahedron around the Ni atom. The dianion links adjacent Ni atoms into a chain, and adjacent chains are held together through the space heterocycle into layers (Fig. 2). Adjacent layers are linked into a network motif by hydrogen bonds (Table 2). The dianion is only monodentate in the 2,2'-bipyridine adduct of nickel phthalate, which exists as a triaqua monohydrate (Poleti et al., 1990).

Experimental top

The compound was synthesized hydrothermally from nickel nitrate hexahydrate (0.29 g, 1 mmol), phthalic anhydride (0.16 g, 1 mmol), 4,4'-bipyridine (0.16 g, 1 mmol) and sodium hydroxide (0.08 g, 2 mmol) in water (18 ml). The mixture was placed into a 20 ml Teflon-lined stainless-steel vessel, which was heated to 443 K for 120 h. The vessel was cooled to room temperature at 5 K h⁻¹. The compound separated from the solution as fine crystals.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1988); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of a fragment of the structure of the title compound at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. [Symmetry codes: (i) x, 1 − y, z; (ii) x, y, 1 + z.]
	Fig. 2. Layer structure of the title compound. The lattice water molecules are not shown.

Aqua(4,4-bipyridine)phthalatonickel(II) trihydrate top

Crystal data top

[Ni(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·3H₂O	F(000) = 468
M_r = 451.07	D_x = 1.578 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 11.134 (2) Å	Cell parameters from 25 reflections
b = 8.379 (2) Å	θ = 12.0–14.0°
c = 11.265 (2) Å	µ = 1.07 mm⁻¹
β = 115.39 (3)°	T = 298 K
V = 949.4 (3) Å³	Plate, green
Z = 2	0.32 × 0.29 × 0.06 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	2171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 30.0°, θ_min = 2.0°
ω scans	h = 0→15
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→11
T_min = 0.455, T_max = 0.939	l = −15→14
3070 measured reflections	2 standard reflections every 60 min
2936 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0777P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.03
2936 reflections	Δρ_max = 0.62 e Å⁻³
262 parameters	Δρ_min = −0.64 e Å⁻³
1 restraint	Absolute structure: Flack & Schwarzenbach (1988)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

[Ni(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·3H₂O	V = 949.4 (3) Å³
M_r = 451.07	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.134 (2) Å	µ = 1.07 mm⁻¹
b = 8.379 (2) Å	T = 298 K
c = 11.265 (2) Å	0.32 × 0.29 × 0.06 mm
β = 115.39 (3)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	2171 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	R_int = 0.059
T_min = 0.455, T_max = 0.939	2 standard reflections every 60 min
3070 measured reflections	intensity decay: none
2936 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.153	Δρ_max = 0.62 e Å⁻³
S = 1.03	Δρ_min = −0.64 e Å⁻³
2936 reflections	Absolute structure: Flack & Schwarzenbach (1988)
262 parameters	Absolute structure parameter: 0.00 (3)
1 restraint

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

	x	y	z	U_iso*/U_eq
Ni1	0.85558 (7)	0.50005 (9)	0.91180 (6)	0.0200 (2)
O1	0.8954 (5)	0.7404 (6)	0.9307 (4)	0.026 (1)
O2	0.9420 (4)	0.9772 (6)	1.0274 (4)	0.025 (1)
O3	0.5322 (6)	0.7523 (8)	0.7245 (5)	0.056 (2)
O4	0.6542 (4)	0.5418 (5)	0.8217 (4)	0.027 (1)
O1w	0.8144 (5)	0.2564 (6)	0.8959 (4)	0.034 (1)
O2w	0.6123 (8)	0.0756 (9)	0.7096 (7)	0.079 (2)
O3w	0.633 (1)	0.049 (2)	0.475 (1)	0.146 (5)
O4w	0.412 (1)	0.240 (2)	0.516 (1)	0.165 (5)
N1	0.8702 (5)	0.4862 (9)	1.1030 (4)	0.025 (1)
N2	0.8460 (4)	0.512 (1)	1.7206 (4)	0.026 (1)
C1	0.8712 (6)	0.8514 (8)	0.9919 (5)	0.021 (1)
C2	0.7571 (6)	0.8385 (8)	1.0286 (6)	0.026 (1)
C3	0.7726 (7)	0.909 (1)	1.1465 (7)	0.036 (2)
C4	0.6773 (8)	0.889 (1)	1.1949 (7)	0.042 (2)
C5	0.5662 (8)	0.805 (1)	1.1237 (7)	0.045 (2)
C6	0.5455 (6)	0.7411 (9)	1.0045 (7)	0.035 (2)
C7	0.6413 (6)	0.7576 (8)	0.9560 (6)	0.027 (1)
C8	0.6107 (6)	0.6764 (9)	0.8250 (6)	0.027 (1)
C9	0.7668 (7)	0.432 (1)	1.1187 (6)	0.033 (2)
C10	0.7576 (6)	0.435 (1)	1.2374 (6)	0.034 (2)
C11	0.8640 (5)	0.496 (1)	1.3483 (5)	0.026 (1)
C12	0.9754 (6)	0.5424 (9)	1.3329 (6)	0.034 (2)
C13	0.9739 (6)	0.5369 (7)	1.2110 (5)	0.027 (2)
C14	0.7780 (7)	0.404 (1)	1.6307 (6)	0.039 (2)
C15	0.7801 (8)	0.395 (1)	1.5076 (7)	0.040 (2)
C16	0.8569 (5)	0.504 (1)	1.4766 (5)	0.027 (1)
C17	0.9257 (7)	0.615 (1)	1.5707 (6)	0.033 (2)
C18	0.9177 (7)	0.6158 (9)	1.6887 (6)	0.031 (2)
H1w1	0.8547	0.1888	0.9573	0.050*
H1w2	0.7415	0.2151	0.8415	0.050*
H2w1	0.5570	0.1183	0.7397	0.050*
H2w2	0.6176	−0.0226	0.7348	0.050*
H3w1	0.6102	−0.0525	0.4557	0.050*
H3w2	0.7171	0.0422	0.5287	0.050*
H4w1	0.4917	0.2320	0.5152	0.050*
H4w2	0.3660	0.1618	0.4628	0.050*
H3	0.8477	0.9701	1.1937	0.043*
H4	0.6902	0.9328	1.2753	0.050*
H5	0.5029	0.7894	1.1560	0.054*
H6	0.4670	0.6866	0.9553	0.042*
H9	0.6959	0.3901	1.0459	0.039*
H10	0.6819	0.3968	1.2433	0.041*
H12	1.0509	0.5771	1.4049	0.041*
H13	1.0495	0.5703	1.2026	0.033*
H14	0.7268	0.3300	1.6505	0.047*
H15	0.7305	0.3180	1.4471	0.048*
H17	0.9781	0.6902	1.5543	0.040*
H18	0.9650	0.6934	1.7499	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0263 (3)	0.0231 (3)	0.0141 (3)	−0.0001 (4)	0.0122 (2)	0.0004 (4)
O1	0.036 (2)	0.021 (2)	0.028 (2)	−0.001 (2)	0.022 (2)	−0.004 (2)
O2	0.027 (2)	0.024 (3)	0.026 (2)	−0.001 (2)	0.013 (2)	−0.004 (2)
O3	0.064 (4)	0.046 (3)	0.036 (3)	0.014 (3)	0.002 (3)	−0.001 (3)
O4	0.027 (2)	0.029 (3)	0.028 (2)	0.003 (2)	0.014 (2)	−0.001 (2)
O1w	0.037 (2)	0.028 (3)	0.031 (2)	0.000 (2)	0.010 (2)	0.005 (2)
O2w	0.088 (5)	0.052 (4)	0.074 (5)	−0.015 (4)	0.014 (4)	0.006 (4)
O3w	0.18 (1)	0.13 (1)	0.105 (7)	−0.055 (9)	0.037 (7)	0.008 (7)
O4w	0.16 (1)	0.14 (1)	0.19 (1)	−0.03 (1)	0.073 (9)	0.01 (1)
N1	0.031 (2)	0.030 (3)	0.020 (2)	0.001 (3)	0.016 (2)	0.001 (3)
N2	0.028 (2)	0.034 (3)	0.018 (2)	−0.001 (3)	0.013 (2)	−0.002 (3)
C1	0.023 (3)	0.025 (3)	0.013 (2)	0.001 (2)	0.006 (2)	0.005 (2)
C2	0.027 (3)	0.029 (3)	0.026 (3)	0.004 (3)	0.015 (2)	−0.002 (3)
C3	0.035 (3)	0.047 (4)	0.034 (3)	0.003 (3)	0.023 (3)	−0.006 (3)
C4	0.049 (4)	0.054 (5)	0.036 (4)	0.006 (4)	0.031 (3)	−0.008 (3)
C5	0.044 (4)	0.061 (5)	0.049 (4)	0.012 (4)	0.037 (3)	0.010 (4)
C6	0.029 (3)	0.036 (4)	0.049 (4)	−0.005 (3)	0.026 (3)	0.001 (3)
C7	0.026 (3)	0.027 (3)	0.033 (3)	0.005 (3)	0.018 (2)	0.003 (3)
C8	0.023 (3)	0.035 (4)	0.026 (3)	−0.002 (3)	0.012 (2)	−0.001 (3)
C9	0.039 (4)	0.044 (4)	0.019 (3)	−0.004 (3)	0.017 (3)	−0.005 (3)
C10	0.030 (3)	0.057 (4)	0.021 (3)	−0.011 (3)	0.017 (3)	−0.002 (3)
C11	0.038 (3)	0.030 (3)	0.016 (2)	0.003 (4)	0.018 (2)	0.002 (4)
C12	0.033 (3)	0.054 (5)	0.017 (2)	−0.010 (3)	0.014 (2)	−0.008 (3)
C13	0.033 (3)	0.032 (4)	0.021 (2)	−0.005 (3)	0.015 (2)	0.004 (2)
C14	0.054 (4)	0.048 (4)	0.018 (3)	−0.022 (4)	0.019 (3)	−0.002 (3)
C15	0.063 (5)	0.044 (4)	0.024 (3)	−0.022 (4)	0.029 (3)	−0.012 (3)
C16	0.032 (3)	0.036 (3)	0.019 (2)	−0.006 (4)	0.017 (2)	−0.004 (4)
C17	0.044 (4)	0.039 (4)	0.025 (3)	−0.014 (3)	0.022 (3)	−0.003 (3)
C18	0.043 (4)	0.039 (4)	0.016 (3)	−0.012 (3)	0.017 (3)	−0.007 (3)

Geometric parameters (Å, º) top

Ni1—O1	2.053 (5)	C12—C13	1.367 (8)
Ni1—O2ⁱ	2.065 (4)	C14—C15	1.398 (9)
Ni1—O4	2.056 (4)	C15—C16	1.39 (1)
Ni1—O1w	2.083 (5)	C16—C17	1.37 (1)
Ni1—N1	2.093 (4)	C17—C18	1.370 (8)
Ni1—N2ⁱⁱ	2.112 (4)	O1w—H1w1	0.86
O1—C1	1.254 (8)	O1w—H1w2	0.85
O2—C1	1.273 (8)	O2w—H2w1	0.90
O3—C8	1.266 (8)	O2w—H2w2	0.87
N1—C9	1.317 (8)	O3w—H3w1	0.88
N1—C13	1.337 (8)	O3w—H3w2	0.87
N2—C14	1.328 (9)	O4w—H4w1	0.89
N2—C18	1.332 (9)	O4w—H4w2	0.89
C1—C2	1.499 (8)	C3—H3	0.93
C2—C7	1.374 (9)	C4—H4	0.93
C2—C3	1.394 (9)	C5—H5	0.93
C3—C4	1.40 (1)	C6—H6	0.93
O4—C8	1.234 (8)	C9—H9	0.93
C4—C5	1.35 (1)	C10—H10	0.93
C5—C6	1.37 (1)	C12—H12	0.93
C7—C8	1.525 (9)	C13—H13	0.93
C9—C10	1.384 (8)	C14—H14	0.93
C10—C11	1.399 (9)	C15—H15	0.93
C11—C12	1.380 (8)	C17—H17	0.93
C11—C16	1.482 (6)	C18—H18	0.93

O1—Ni1—O2ⁱ	84.3 (2)	C12—C11—C10	117.0 (5)
O1—Ni1—O4	91.5 (2)	C12—C11—C16	122.5 (5)
O1—Ni1—O1w	178.9 (2)	C10—C11—C16	120.5 (5)
O1—Ni1—N1	91.7 (2)	C13—C12—C11	119.5 (6)
O1—Ni1—N2ⁱⁱ	88.5 (3)	N1—C13—C12	123.9 (6)
O2ⁱ—Ni1—O4	169.7 (2)	N2—C14—C15	123.0 (6)
O2ⁱ—Ni1—O1w	96.1 (2)	C16—C15—C14	119.3 (6)
O2ⁱ—Ni1—N1	93.6 (2)	C17—C16—C15	116.7 (5)
O2ⁱ—Ni1—N2ⁱⁱ	85.0 (2)	C17—C16—C11	122.5 (6)
O4—Ni1—O1w	88.4 (2)	C15—C16—C11	120.9 (6)
O4—Ni1—N1	96.0 (2)	C18—C17—C16	120.4 (6)
O4—Ni1—N2ⁱⁱ	85.5 (2)	N2—C18—C17	123.7 (6)
O1w—Ni1—N1	87.2 (2)	Ni1—O1w—H1w1	124
O1w—Ni1—N2ⁱⁱ	92.6 (3)	Ni1—O1w—H1w2	124
N1—Ni1—N2ⁱⁱ	178.5 (2)	H1w1—O1w—H1w2	109
C1—O1—Ni1	134.2 (4)	H2w1—O2w—H2w2	103
C1—O2—Ni1ⁱⁱⁱ	128.4 (4)	H3w1—O3w—H3w2	103
C8—O4—Ni1	120.0 (4)	H4w1—O4w—H4w2	103
C9—N1—C13	116.8 (5)	C2—C3—H3	119.4
C9—N1—Ni1	118.1 (4)	C4—C3—H3	119.4
C13—N1—Ni1	125.0 (4)	C5—C4—H4	120.4
C14—N2—C18	116.8 (5)	C3—C4—H4	120.4
C14—N2—Ni1^iv	120.6 (5)	C4—C5—H5	119.6
C18—N2—Ni1^iv	122.1 (4)	C6—C5—H5	119.6
O1—C1—O2	122.5 (5)	C5—C6—H6	119.7
O1—C1—C2	120.3 (6)	C7—C6—H6	119.7
O2—C1—C2	117.1 (5)	N1—C9—H9	118.2
C7—C2—C3	118.4 (6)	C10—C9—H9	118.2
C7—C2—C1	124.2 (5)	C9—C10—H10	120.5
C3—C2—C1	117.3 (6)	C11—C10—H10	120.5
C2—C3—C4	121.2 (7)	C13—C12—H12	120.3
C5—C4—C3	119.2 (7)	C11—C12—H12	120.3
C4—C5—C6	120.7 (7)	N1—C13—H13	118.0
C5—C6—C7	120.7 (7)	C12—C13—H13	118.0
C2—C7—C6	119.6 (6)	N2—C14—H14	118.5
C2—C7—C8	124.0 (5)	C15—C14—H14	118.5
C6—C7—C8	116.3 (6)	C16—C15—H15	120.3
O4—C8—O3	124.2 (6)	C14—C15—H15	120.3
O4—C8—C7	120.6 (6)	C18—C17—H17	119.8
O3—C8—C7	115.1 (6)	C16—C17—H17	119.8
N1—C9—C10	123.7 (6)	N2—C18—H18	118.1
C9—C10—C11	118.9 (6)	C17—C18—H18	118.1

O4—Ni1—O1—C1	63.6 (6)	C1—C2—C7—C8	−3 (1)
O2ⁱ—Ni1—O1—C1	−125.8 (6)	C5—C6—C7—C2	0 (1)
N1—Ni1—O1—C1	−32.4 (6)	C5—C6—C7—C8	177.5 (7)
N2ⁱⁱ—Ni1—O1—C1	149.1 (6)	Ni1—O4—C8—O3	127.4 (6)
O1—Ni1—O4—C8	−13.5 (5)	Ni1—O4—C8—C7	−57.6 (7)
O2ⁱ—Ni1—O4—C8	−79 (1)	C2—C7—C8—O4	82.2 (9)
O1w—Ni1—O4—C8	165.3 (5)	C6—C7—C8—O4	−95.3 (7)
N1—Ni1—O4—C8	78.3 (5)	C2—C7—C8—O3	−102.3 (8)
N2ⁱⁱ—Ni1—O4—C8	−102.0 (5)	C6—C7—C8—O3	80.2 (8)
O1—Ni1—N1—C9	122.3 (6)	C13—N1—C9—C10	4 (1)
O4—Ni1—N1—C9	30.6 (6)	Ni1—N1—C9—C10	−172.1 (6)
O2ⁱ—Ni1—N1—C9	−153.4 (6)	N1—C9—C10—C11	−1 (1)
O1w—Ni1—N1—C9	−57.4 (6)	C9—C10—C11—C12	−3 (1)
O1—Ni1—N1—C13	−53.6 (6)	C9—C10—C11—C16	178.9 (7)
O4—Ni1—N1—C13	−145.2 (6)	C10—C11—C12—C13	4 (1)
O2ⁱ—Ni1—N1—C13	30.8 (6)	C16—C11—C12—C13	−178.1 (7)
O1w—Ni1—N1—C13	126.8 (6)	C9—N1—C13—C12	−3 (1)
Ni1—O1—C1—O2	154.7 (4)	Ni1—N1—C13—C12	172.7 (5)
Ni1—O1—C1—C2	−24.0 (8)	C11—C12—C13—N1	−1 (1)
Ni1ⁱⁱⁱ—O2—C1—O1	−34.6 (8)	C18—N2—C14—C15	0 (1)
Ni1ⁱⁱⁱ—O2—C1—C2	144.2 (4)	Ni1^iv—N2—C14—C15	−172.8 (6)
O1—C1—C2—C7	−31.5 (9)	N2—C14—C15—C16	1 (1)
O2—C1—C2—C7	149.7 (6)	C14—C15—C16—C17	−1 (1)
O1—C1—C2—C3	146.2 (6)	C14—C15—C16—C11	178.6 (7)
O2—C1—C2—C3	−32.6 (8)	C12—C11—C16—C17	30 (1)
C7—C2—C3—C4	4 (1)	C10—C11—C16—C17	−152.4 (9)
C1—C2—C3—C4	−173.4 (7)	C12—C11—C16—C15	−149.4 (9)
C2—C3—C4—C5	−2 (1)	C10—C11—C16—C15	28 (1)
C3—C4—C5—C6	−1 (1)	C15—C16—C17—C18	0 (1)
C4—C5—C6—C7	2 (1)	C11—C16—C17—C18	−179.0 (7)
C3—C2—C7—C6	−3 (1)	C14—N2—C18—C17	−1 (1)
C1—C2—C7—C6	174.6 (6)	Ni1^iv—N2—C18—C17	172.2 (6)
C3—C2—C7—C8	179.5 (7)	C16—C17—C18—N2	1 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w2···O2w	0.85	1.95	2.778 (9)	162
O1w—H1w1···O2^v	0.86	2.01	2.807 (7)	154
O2w—H2w2···O3^v	0.87	2.09	2.88 (1)	151
O3w—H3w1···O4w^vi	0.88	1.80	2.64 (2)	158
O4w—H4w1···O2w	0.89	2.40	2.73 (2)	102
O4w—H4w1···O3w	0.89	2.38	3.14 (2)	142

Symmetry codes: (v) x, y−1, z; (vi) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₄O₄)(C₁₀H₈N₂)(H₂O)]·3H₂O
M_r	451.07
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	11.134 (2), 8.379 (2), 11.265 (2)
β (°)	115.39 (3)
V (Å³)	949.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.32 × 0.29 × 0.06

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	Empirical (using intensity measurements) via ψ scan (North et al., 1968)
T_min, T_max	0.455, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	3070, 2936, 2171
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.153, 1.03
No. of reflections	2936
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.64
Absolute structure	Flack & Schwarzenbach (1988)
Absolute structure parameter	0.00 (3)

Computer programs: CAD-4 Software (Enraf-Nonius, 1988), CAD-4 Software, XCAD4 (Harms, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top

Ni1—O1	2.053 (5)	Ni1—O1w	2.083 (5)
Ni1—O2ⁱ	2.065 (4)	Ni1—N1	2.093 (4)
Ni1—O4	2.056 (4)	Ni1—N2ⁱⁱ	2.112 (4)

O1—Ni1—O2ⁱ	84.3 (2)	O2ⁱ—Ni1—N2ⁱⁱ	85.0 (2)
O1—Ni1—O4	91.5 (2)	O4—Ni1—O1w	88.4 (2)
O1—Ni1—O1w	178.9 (2)	O4—Ni1—N1	96.0 (2)
O1—Ni1—N1	91.7 (2)	O4—Ni1—N2ⁱⁱ	85.5 (2)
O1—Ni1—N2ⁱⁱ	88.5 (3)	O1w—Ni1—N1	87.2 (2)
O2ⁱ—Ni1—O4	169.7 (2)	O1w—Ni1—N2ⁱⁱ	92.6 (3)
O2ⁱ—Ni1—O1w	96.1 (2)	N1—Ni1—N2ⁱⁱ	178.5 (2)
O2ⁱ—Ni1—N1	93.6 (2)

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