{2,2′-[o-Phenyl­enebis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) monohydrate

Ghaemi, A.; Fayyazi, K.; Keyvani, B.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811039730

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages m1481-m1482

doi:10.1107/S1600536811039730

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{2,2′-[o-Phenylenebis(nitrilomethanylylidene)]diphenolato-κ⁴O,N,N′,O′}nickel(II) monohydrate

Akbar Ghaemi,^a ‡ Kazem Fayyazi,^a Bahram Keyvani,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Saveh Branch, Islamic Azad University, Saveh, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 September 2011; accepted 27 September 2011; online 5 October 2011)

The Ni^II atom in the title monohydrate, [Ni(C₂₀H₁₄N₂O₂)]·H₂O, is coordinated within a cis-N₂O₂ square-planar donor set provided by the tetradentate Schiff base ligand. Overall, the molecule has a curved shape with the dihedral angle formed between the planes of the outer benzene rings being 13.92 (18)°. The water molecule was found to be disordered over two positions [ratio 0.80 (1):0.20 (1)] and the major component is linked to the complex via an O—H⋯O hydrogen bond.

Related literature

For background to the catalytic potential of transition metal Schiff base complexes, see: Gupta & Sutar (2008). For the structure of the unsolvated form of the title complex. see: Radha et al. (1985 ); Wang et al. (2003 ). For our recent work in this area, see: Ghaemi et al. (2011 ).

Experimental

Crystal data

[Ni(C₂₀H₁₄N₂O₂)]·H₂O
M_r = 391.06
Trigonal, $[R \overline 3]$
a = 31.5519 (13) Å
c = 9.0255 (6) Å
V = 7781.3 (6) Å³
Z = 18
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 294 K
0.30 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.732, T_max = 1.0
13452 measured reflections
3897 independent reflections
2850 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.04
3897 reflections
251 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni—O1	1.8865 (18)
Ni—O2	1.886 (2)
Ni—N1	1.930 (2)
Ni—N2	1.935 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯O1	0.83 (1)	2.06 (2)	2.842 (4)	158 (5)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039730/hb6421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039730/hb6421Isup2.hkl

checkCIF report

Comment top

Schiff base complexes of transition metal ions are efficient catalysts both in homo- and hetero-geneous reactions, and the activity of these complexes varies with the type of ligand, coordination sites and metal ions (Gupta & Sutar, 2008). In continuation of work in this area (Ghaemi et al., 2011), the title complex, (I), was isolated as a monohydrate and characterized crystallographically. An unsolvated form has been characterized previously (Radha et al., 1985; Wang et al., 2003).

The Ni^II atom in the complex exists within a cis-N₂O₂ donor set defined by the tetradentate Schiff base ligand, Fig. 1 and Table 1. The respective pairs of Ni—O and Ni—N bond distances are equal within experimental error. The greatest deviation from the ideal square planar angles is seen in the N1—Ni—N2 chelate angle of 83.98 (9)°. Some minor buckling is found in the N₂O₂ donor set with the r.m.s. deviation being 0.0548 Å. The maximum deviations from the least-squares plane are 0.0550 (10) and -0.0552 (10) Å for the N1 and N2 atoms, respectively, and the Ni atom lies 0.0002 (11) Å out of the least-squares plane. Each of the chelate rings is essentially planar. Thus, the r.m.s. deviation for the five-membered ring is 0.046 Å, and the equivalent values for the O1- and O2-containing six-membered chelate rings are 0.013 and 0.097 Å, respectively. The dihedral angle formed between the outer benzene rings is 13.92 (18)°, indicating that overall the molecule has a slightly curved shape.

The water molecule of solvation is associated with the complex molecule, forming a hydrogen bond with the O1 atom. Disorder in the position of the water molecule precludes a detailed analysis of the supramolecular structure.

Related literature top

For background to the catalytic potential of transition metal Schiff base complexes, see: Gupta & Sutar (2008). For the structure of the unsolvated form of the title complex. see: Radha et al. (1985); Wang et al.(2003). For our recent work in this area, see: Ghaemi et al. (2011).

Experimental top

N,N'-Bis(2-hydroxybenzylidene)-o-phenylenediamine was prepared by the following procedure. To a stirred ethanolic solution (30 ml) of o-phenylenediamine (0.108 g, 1 mmol), 2-hydroxybenzaldehyde (0.244 g, 2 mmol) was added. The bright-yellow solution was stirred and heated to reflux for 1 h. A yellow precipitate was obtained that was filtered off, washed with diethyl ether; yield: 75%. The title complex was obtained by the following procedure. The Schiff base ligand (0.316 g, 1 mmol) was dissolved in 20 ml e thanol. A solution of nickel(II) acetate (0.248 g, 1 mmol) in ethanol was added to the solution of ligand and the reaction mixture was refluxed for 1 h. The product washed with ethanol and air dried; yield: 85%. Dark brown blocks of the title complex were obtained from its 5:1 acetone and methanol mixture (v/v) by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level. Only the major component of the disordered water molecule is illustrated.

{2,2'-[o-Phenylenebis(nitrilomethanylylidene)]diphenolato- κ⁴O,N,N',O'}nickel(II) monohydrate top

Crystal data top

[Ni(C₂₀H₁₄N₂O₂)]·H₂O	D_x = 1.502 Mg m⁻³
M_r = 391.06	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 4020 reflections
Hall symbol: -R 3	θ = 2.2–29.2°
a = 31.5519 (13) Å	µ = 1.14 mm⁻¹
c = 9.0255 (6) Å	T = 294 K
V = 7781.3 (6) Å³	Block, dark-brown
Z = 18	0.30 × 0.15 × 0.15 mm
F(000) = 3636

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3897 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2850 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −40→39
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −30→40
T_min = 0.732, T_max = 1.0	l = −11→11
13452 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0632P)² + 2.9091P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.52 e Å⁻³
3 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₂₀H₁₄N₂O₂)]·H₂O	Z = 18
M_r = 391.06	Mo Kα radiation
Trigonal, R3	µ = 1.14 mm⁻¹
a = 31.5519 (13) Å	T = 294 K
c = 9.0255 (6) Å	0.30 × 0.15 × 0.15 mm
V = 7781.3 (6) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3897 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2850 reflections with I > 2σ(I)
T_min = 0.732, T_max = 1.0	R_int = 0.036
13452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.52 e Å⁻³
3897 reflections	Δρ_min = −0.43 e Å⁻³
251 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)
Ni	0.517165 (12)	0.069858 (12)	0.75915 (3)	0.04310 (14)
O1	0.46763 (7)	0.05129 (7)	0.9031 (2)	0.0534 (5)
O2	0.53199 (8)	0.13507 (8)	0.7881 (2)	0.0663 (6)
O1W	0.49982 (18)	0.12723 (16)	1.1173 (4)	0.0839 (16)	0.799 (10)
O1W'	0.5396 (7)	0.1609 (5)	1.128 (2)	0.081 (6)	0.201 (10)
H1	0.4901 (17)	0.1108 (15)	1.040 (3)	0.122*
H2	0.5295 (9)	0.149 (2)	1.109 (7)	0.122*
N1	0.50665 (8)	0.00460 (8)	0.7325 (2)	0.0433 (5)
N2	0.56480 (8)	0.08656 (8)	0.6025 (2)	0.0461 (5)
C1	0.43849 (9)	0.00727 (10)	0.9530 (3)	0.0442 (6)
C2	0.40283 (10)	0.00071 (12)	1.0577 (3)	0.0518 (7)
H2A	0.4003	0.0276	1.0871	0.062*
C3	0.37181 (10)	−0.04400 (12)	1.1177 (3)	0.0558 (7)
H3	0.3485	−0.0471	1.1865	0.067*
C4	0.37476 (11)	−0.08475 (12)	1.0770 (3)	0.0594 (8)
H4	0.3539	−0.1151	1.1191	0.071*
C5	0.40858 (10)	−0.07978 (12)	0.9743 (3)	0.0559 (7)
H5	0.4104	−0.1072	0.9465	0.067*
C6	0.44089 (10)	−0.03438 (10)	0.9090 (3)	0.0454 (6)
C7	0.47473 (10)	−0.03337 (10)	0.8036 (3)	0.0457 (6)
H7	0.4738	−0.0628	0.7842	0.055*
C8	0.53948 (9)	0.00265 (10)	0.6283 (3)	0.0440 (6)
C9	0.54204 (11)	−0.03870 (11)	0.5953 (3)	0.0523 (7)
H9	0.5209	−0.0685	0.6403	0.063*
C10	0.57666 (12)	−0.03518 (13)	0.4942 (3)	0.0616 (8)
H10	0.5784	−0.0630	0.4704	0.074*
C11	0.60844 (11)	0.00867 (13)	0.4287 (3)	0.0598 (8)
H11	0.6317	0.0105	0.3617	0.072*
C12	0.60606 (10)	0.04971 (12)	0.4617 (3)	0.0547 (7)
H12	0.6279	0.0795	0.4183	0.066*
C13	0.57083 (9)	0.04682 (11)	0.5604 (3)	0.0446 (6)
C14	0.58649 (11)	0.12823 (12)	0.5356 (3)	0.0573 (7)
H14	0.6062	0.1312	0.4551	0.069*
C15	0.58292 (11)	0.16991 (11)	0.5738 (3)	0.0585 (7)
C16	0.60823 (15)	0.21219 (14)	0.4862 (4)	0.0843 (11)
H16	0.6253	0.2110	0.4038	0.101*
C17	0.60896 (16)	0.25426 (14)	0.5161 (5)	0.0889 (11)
H17	0.6255	0.2813	0.4543	0.107*
C18	0.58475 (14)	0.25664 (13)	0.6400 (5)	0.0827 (11)
H18	0.5858	0.2858	0.6635	0.099*
C19	0.55925 (13)	0.21665 (13)	0.7291 (5)	0.0774 (10)
H19	0.5428	0.2191	0.8112	0.093*
C20	0.55721 (11)	0.17190 (11)	0.6999 (3)	0.0571 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0432 (2)	0.0485 (2)	0.0423 (2)	0.02653 (17)	0.00544 (14)	0.00408 (14)
O1	0.0591 (12)	0.0557 (12)	0.0528 (10)	0.0342 (10)	0.0125 (9)	0.0075 (9)
O2	0.0752 (15)	0.0579 (13)	0.0735 (13)	0.0390 (12)	0.0244 (11)	0.0102 (11)
O1W	0.104 (4)	0.077 (3)	0.073 (2)	0.047 (3)	0.0052 (19)	−0.0180 (17)
O1W'	0.085 (12)	0.046 (9)	0.123 (11)	0.041 (9)	0.002 (8)	−0.005 (7)
N1	0.0423 (12)	0.0541 (13)	0.0354 (10)	0.0255 (11)	−0.0041 (9)	−0.0004 (9)
N2	0.0407 (12)	0.0571 (14)	0.0417 (10)	0.0252 (11)	−0.0020 (9)	0.0009 (10)
C1	0.0427 (14)	0.0569 (16)	0.0363 (12)	0.0274 (13)	−0.0026 (11)	0.0060 (11)
C2	0.0486 (16)	0.0707 (19)	0.0419 (13)	0.0341 (15)	0.0008 (12)	0.0025 (13)
C3	0.0446 (15)	0.080 (2)	0.0409 (13)	0.0293 (16)	0.0013 (12)	0.0049 (14)
C4	0.0476 (16)	0.0648 (19)	0.0514 (15)	0.0172 (15)	0.0003 (13)	0.0110 (14)
C5	0.0515 (17)	0.0613 (18)	0.0531 (15)	0.0270 (15)	−0.0010 (13)	0.0019 (14)
C6	0.0429 (14)	0.0567 (16)	0.0391 (12)	0.0267 (13)	−0.0028 (11)	0.0027 (12)
C7	0.0473 (15)	0.0508 (15)	0.0419 (12)	0.0266 (13)	−0.0053 (12)	−0.0019 (12)
C8	0.0400 (14)	0.0608 (17)	0.0354 (12)	0.0284 (13)	−0.0068 (10)	−0.0063 (12)
C9	0.0538 (16)	0.0594 (18)	0.0474 (14)	0.0311 (15)	−0.0048 (13)	−0.0087 (13)
C10	0.066 (2)	0.076 (2)	0.0523 (16)	0.0428 (18)	−0.0050 (15)	−0.0175 (16)
C11	0.0526 (17)	0.084 (2)	0.0502 (15)	0.0399 (17)	0.0007 (13)	−0.0127 (15)
C12	0.0471 (16)	0.0686 (19)	0.0464 (14)	0.0274 (15)	0.0010 (12)	−0.0033 (14)
C13	0.0387 (14)	0.0627 (17)	0.0344 (11)	0.0269 (13)	−0.0063 (11)	−0.0053 (12)
C14	0.0477 (16)	0.066 (2)	0.0518 (15)	0.0237 (15)	0.0072 (13)	0.0060 (14)
C15	0.0519 (17)	0.0570 (18)	0.0622 (17)	0.0239 (15)	0.0021 (14)	0.0096 (14)
C16	0.088 (3)	0.072 (2)	0.085 (2)	0.034 (2)	0.020 (2)	0.021 (2)
C17	0.091 (3)	0.060 (2)	0.103 (3)	0.029 (2)	0.015 (2)	0.022 (2)
C18	0.079 (2)	0.054 (2)	0.115 (3)	0.0332 (19)	0.005 (2)	0.010 (2)
C19	0.068 (2)	0.059 (2)	0.108 (3)	0.0333 (18)	0.014 (2)	0.007 (2)
C20	0.0512 (17)	0.0544 (18)	0.0683 (18)	0.0283 (15)	0.0026 (14)	0.0082 (15)

Geometric parameters (Å, º) top

Ni—O1	1.8865 (18)	C6—C7	1.419 (4)
Ni—O2	1.886 (2)	C7—H7	0.9300
Ni—N1	1.930 (2)	C8—C9	1.379 (4)
Ni—N2	1.935 (2)	C8—C13	1.385 (4)
O1—C1	1.304 (3)	C9—C10	1.385 (4)
O2—C20	1.301 (3)	C9—H9	0.9300
O1W—O1W'	1.175 (15)	C10—C11	1.372 (5)
O1W—H1	0.829 (10)	C10—H10	0.9300
O1W—H2	0.841 (10)	C11—C12	1.367 (4)
O1W'—H2	0.39 (4)	C11—H11	0.9300
N1—C7	1.286 (3)	C12—C13	1.391 (4)
N1—C8	1.423 (3)	C12—H12	0.9300
N2—C14	1.289 (4)	C14—C15	1.417 (4)
N2—C13	1.411 (3)	C14—H14	0.9300
C1—C2	1.403 (4)	C15—C16	1.406 (5)
C1—C6	1.410 (4)	C15—C20	1.417 (4)
C2—C3	1.364 (4)	C16—C17	1.343 (5)
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.384 (4)	C17—C18	1.378 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.362 (4)	C18—C19	1.368 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.407 (4)	C19—C20	1.406 (4)
C5—H5	0.9300	C19—H19	0.9300

O2—Ni—O1	87.61 (9)	C9—C8—C13	120.4 (2)
O2—Ni—N1	176.06 (9)	C9—C8—N1	124.8 (3)
O1—Ni—N1	94.63 (9)	C13—C8—N1	114.7 (2)
O2—Ni—N2	93.96 (9)	C8—C9—C10	118.9 (3)
O1—Ni—N2	176.40 (9)	C8—C9—H9	120.6
N1—Ni—N2	83.98 (9)	C10—C9—H9	120.6
C1—O1—Ni	127.01 (17)	C11—C10—C9	121.0 (3)
C20—O2—Ni	126.63 (19)	C11—C10—H10	119.5
O1W'—O1W—H1	122 (4)	C9—C10—H10	119.5
O1W'—O1W—H2	12 (4)	C12—C11—C10	120.2 (3)
H1—O1W—H2	110.1 (18)	C12—C11—H11	119.9
O1W—O1W'—H2	27 (8)	C10—C11—H11	119.9
C7—N1—C8	122.5 (2)	C11—C12—C13	119.9 (3)
C7—N1—Ni	124.63 (18)	C11—C12—H12	120.1
C8—N1—Ni	112.83 (17)	C13—C12—H12	120.1
C14—N2—C13	122.8 (2)	C8—C13—C12	119.6 (3)
C14—N2—Ni	124.3 (2)	C8—C13—N2	115.4 (2)
C13—N2—Ni	112.72 (17)	C12—C13—N2	124.9 (3)
O1—C1—C2	118.4 (3)	N2—C14—C15	125.8 (3)
O1—C1—C6	123.9 (2)	N2—C14—H14	117.1
C2—C1—C6	117.7 (3)	C15—C14—H14	117.1
C3—C2—C1	121.8 (3)	C16—C15—C20	118.4 (3)
C3—C2—H2A	119.1	C16—C15—C14	118.2 (3)
C1—C2—H2A	119.1	C20—C15—C14	123.3 (3)
C2—C3—C4	120.6 (3)	C17—C16—C15	123.1 (4)
C2—C3—H3	119.7	C17—C16—H16	118.5
C4—C3—H3	119.7	C15—C16—H16	118.5
C5—C4—C3	119.1 (3)	C16—C17—C18	118.7 (4)
C5—C4—H4	120.5	C16—C17—H17	120.6
C3—C4—H4	120.5	C18—C17—H17	120.6
C4—C5—C6	122.0 (3)	C19—C18—C17	120.9 (4)
C4—C5—H5	119.0	C19—C18—H18	119.5
C6—C5—H5	119.0	C17—C18—H18	119.5
C5—C6—C1	118.8 (2)	C18—C19—C20	121.8 (4)
C5—C6—C7	117.3 (3)	C18—C19—H19	119.1
C1—C6—C7	123.9 (3)	C20—C19—H19	119.1
N1—C7—C6	125.8 (3)	O2—C20—C19	118.9 (3)
N1—C7—H7	117.1	O2—C20—C15	124.1 (3)
C6—C7—H7	117.1	C19—C20—C15	117.1 (3)

O2—Ni—O1—C1	−178.2 (2)	Ni—N1—C8—C9	175.7 (2)
N1—Ni—O1—C1	−1.4 (2)	C7—N1—C8—C13	179.0 (2)
N2—Ni—O1—C1	65.8 (15)	Ni—N1—C8—C13	−3.1 (3)
O1—Ni—O2—C20	−162.7 (3)	C13—C8—C9—C10	0.4 (4)
N1—Ni—O2—C20	72.5 (13)	N1—C8—C9—C10	−178.3 (2)
N2—Ni—O2—C20	14.1 (3)	C8—C9—C10—C11	0.8 (4)
O2—Ni—N1—C7	123.7 (12)	C9—C10—C11—C12	−0.6 (4)
O1—Ni—N1—C7	−0.9 (2)	C10—C11—C12—C13	−0.9 (4)
N2—Ni—N1—C7	−177.6 (2)	C9—C8—C13—C12	−1.9 (4)
O2—Ni—N1—C8	−54.1 (13)	N1—C8—C13—C12	177.0 (2)
O1—Ni—N1—C8	−178.72 (16)	C9—C8—C13—N2	179.9 (2)
N2—Ni—N1—C8	4.61 (16)	N1—C8—C13—N2	−1.2 (3)
O2—Ni—N2—C14	−13.2 (2)	C11—C12—C13—C8	2.2 (4)
O1—Ni—N2—C14	102.7 (14)	C11—C12—C13—N2	−179.8 (2)
N1—Ni—N2—C14	170.2 (2)	C14—N2—C13—C8	−170.6 (2)
O2—Ni—N2—C13	171.37 (17)	Ni—N2—C13—C8	5.0 (3)
O1—Ni—N2—C13	−72.8 (14)	C14—N2—C13—C12	11.3 (4)
N1—Ni—N2—C13	−5.26 (16)	Ni—N2—C13—C12	−173.1 (2)
Ni—O1—C1—C2	−178.18 (17)	C13—N2—C14—C15	−178.6 (3)
Ni—O1—C1—C6	2.5 (4)	Ni—N2—C14—C15	6.4 (4)
O1—C1—C2—C3	−178.4 (2)	N2—C14—C15—C16	−178.5 (3)
C6—C1—C2—C3	1.0 (4)	N2—C14—C15—C20	4.8 (5)
C1—C2—C3—C4	0.3 (4)	C20—C15—C16—C17	−0.4 (6)
C2—C3—C4—C5	−1.0 (4)	C14—C15—C16—C17	−177.2 (4)
C3—C4—C5—C6	0.5 (4)	C15—C16—C17—C18	1.5 (6)
C4—C5—C6—C1	0.8 (4)	C16—C17—C18—C19	−1.8 (7)
C4—C5—C6—C7	179.8 (3)	C17—C18—C19—C20	1.0 (6)
O1—C1—C6—C5	177.8 (2)	Ni—O2—C20—C19	171.7 (2)
C2—C1—C6—C5	−1.5 (4)	Ni—O2—C20—C15	−7.9 (4)
O1—C1—C6—C7	−1.1 (4)	C18—C19—C20—O2	−179.4 (3)
C2—C1—C6—C7	179.5 (2)	C18—C19—C20—C15	0.2 (5)
C8—N1—C7—C6	179.9 (2)	C16—C15—C20—O2	179.1 (3)
Ni—N1—C7—C6	2.3 (4)	C14—C15—C20—O2	−4.2 (5)
C5—C6—C7—N1	179.6 (2)	C16—C15—C20—C19	−0.5 (5)
C1—C6—C7—N1	−1.5 (4)	C14—C15—C20—C19	176.2 (3)
C7—N1—C8—C9	−2.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O1	0.83 (1)	2.06 (2)	2.842 (4)	158 (5)

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₁₄N₂O₂)]·H₂O
M_r	391.06
Crystal system, space group	Trigonal, R3
Temperature (K)	294
a, c (Å)	31.5519 (13), 9.0255 (6)
V (Å³)	7781.3 (6)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.30 × 0.15 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.732, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	13452, 3897, 2850
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.04
No. of reflections	3897
No. of parameters	251
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.43

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni—O1	1.8865 (18)	Ni—N1	1.930 (2)
Ni—O2	1.886 (2)	Ni—N2	1.935 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O1	0.829 (10)	2.06 (2)	2.842 (4)	158 (5)

Footnotes

‡Additional correspondence author, e-mail: akbarghaemi@yahoo.com.

Acknowledgements

We gratefully acknowledge practical support of this study by the Islamic Azad University (Saveh Branch), and thank the University of Malaya for supporting the crystallographic facility.

References

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