Diaqua­bis­{2-hy­droxy-5-[(pyridin-2-yl)methyl­idene­amino]­benzoato-κ2N,N′}nickel(II) dihydrate

Zha, M.; Li, X.; Bing, Y.; Luo, Z.

doi:10.1107/S1600536810046118

metal-organic compounds

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Volume 66| Part 12| December 2010| Page m1570

https://doi.org/10.1107/S1600536810046118

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Diaquabis{2-hydroxy-5-[(pyridin-2-yl)methylideneamino]benzoato-κ²N,N′}nickel(II) dihydrate

Meiqin Zha,^a Xing Li,^a ^* Yue Bing ^a and Zhengbing Luo ^a

^aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: lix905@126.com

(Received 29 October 2010; accepted 9 November 2010; online 13 November 2010)

In the title complex, [Ni(C₁₃H₉N₂O₃)₂(H₂O)₂]·2H₂O, the Ni^II atom, located on a twofold rotation axis, is in a distorted octahedral geometry, defined by four N atoms from two 2-hydroxy-5-[(pyridin-2-yl)methylideneamino]benzoate ligands and two O atoms from two water molecules. In the crystal, intermolecular O—H⋯O hydrogen bonds link the complex molecules and uncoordinated water molecules into a three-dimensional network. Intramolecular O—H⋯O hydrogen bonds are present between the hydroxy and carboxylate groups.

Related literature

For the biological activity of Schiff base compounds, see: Ali et al. (2002 ); Cukurovali et al. (2002 ); Tarafder et al. (2002 ).

Experimental

Crystal data

[Ni(C₁₃H₉N₂O₃)₂(H₂O)₂]·2H₂O
M_r = 613.22
Orthorhombic, P b c n
a = 15.7628 (6) Å
b = 10.5672 (3) Å
c = 15.6178 (6) Å
V = 2601.44 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 173 K
0.41 × 0.34 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.725, T_max = 0.907
14975 measured reflections
2294 independent reflections
1599 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.074
S = 0.89
2294 reflections
202 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1	0.84	1.72	2.475 (2)	149
O4—H4B⋯O2ⁱ	0.83 (2)	1.81 (2)	2.621 (2)	168 (3)
O4—H4C⋯O5	0.84 (2)	1.91 (2)	2.744 (3)	173 (2)
O5—H5B⋯O3ⁱⁱ	0.82 (2)	2.05 (2)	2.870 (3)	178 (3)
O5—H5C⋯O1ⁱⁱⁱ	0.84 (2)	1.99 (2)	2.793 (3)	160 (3)
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: https://doi.org/10.1107/S1600536810046118/hy2372sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046118/hy2372Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in antitumor, antimicrobial and antiviral activities (Ali et al., 2002; Cukurovali et al., 2002; Tarafder et al., 2002). As an extension of the work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

The title compound is a mononuclear nickel(II) complex, as shown in Fig. 1. The Ni^II atom, lying on a twofold rotation axis, is six-coordinated in a distorted octahedral geometry, defined by four N donors from two Schiff base ligands, two O atoms from two coordinated water molecules. The molecular formula contains two uncoordinated water molecules. The Ni—N bond lengths are 2.0754 (18) and 2.1347 (17) Å, and the Ni—O distance is 2.0380 (17) Å. Intramolecular O—H···O hydrogen bonds between the hydroxy and carboxylate groups are observed (Table 1). In the crystal, intermolecular O—H···O hydrogen bonds link the complex molecules and uncoordinated water molecules into a three-dimensional network (Fig. 2).

Related literature top

For the biological activity of Schiff base compounds, see: Ali et al. (2002); Cukurovali et al. (2002); Tarafder et al. (2002).

Experimental top

5-Aminosalicylic acid (1.53 g, 10 mmol), 2-pyridinecarboxaldehyde (1 ml, 10 mmol) and triethylamine (1 ml, 10 mmol) were mixed in 50 ml ethanol in a round flask. The mixture was refluxed with agitation for 4 h at 323 K to give a yellow precipitate. After filtration and washing the precipitate with ethanol, a pure Schiff base ligand, 5-[(pyridin-2-yl)methyleneamino]-2-hydroxybenzoic acid (yield: 2.02 g, 84%) was obtained.

A mixture of 5-[(pyridin-2-yl)methyleneamino]-2-hydroxybenzoic acid (0.024 g, 0.1 mmol), Ni(CH₃CO₂)₂.2H₂O (0.025 g, 0.1 mmol) and ethanol (20 ml) was heated at 273 K for 30 min to give a red solution. After evaporating the solution at room temperature for one week, red crystals were obtained (yield: 65%).

Structure description top

For the biological activity of Schiff base compounds, see: Ali et al. (2002); Cukurovali et al. (2002); Tarafder et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (A) -x+1, y, -z+1/2.]
	Fig. 2. Three-dimensional supramolecular network in the title compound. Dashed lines denote hydrogen bonds.

Diaquabis{2-hydroxy-5-[(pyridin-2-yl)methylideneamino]benzoato- κ²N,N'}nickel(II) dihydrate top

Crystal data top

[Ni(C₁₃H₉N₂O₃)₂(H₂O)₂]·2H₂O	F(000) = 1272
M_r = 613.22	D_x = 1.566 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 14975 reflections
a = 15.7628 (6) Å	θ = 3.9–25.0°
b = 10.5672 (3) Å	µ = 0.81 mm⁻¹
c = 15.6178 (6) Å	T = 173 K
V = 2601.44 (16) Å³	Platelet, red
Z = 4	0.41 × 0.34 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	2294 independent reflections
Radiation source: fine-focus sealed tube	1599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 25.0°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.725, T_max = 0.907	k = −12→12
14975 measured reflections	l = −18→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.045P)²] where P = (F_o² + 2F_c²)/3
2294 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.20 e Å⁻³
4 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ni(C₁₃H₉N₂O₃)₂(H₂O)₂]·2H₂O	V = 2601.44 (16) Å³
M_r = 613.22	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 15.7628 (6) Å	µ = 0.81 mm⁻¹
b = 10.5672 (3) Å	T = 173 K
c = 15.6178 (6) Å	0.41 × 0.34 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	2294 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1599 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.907	R_int = 0.044
14975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	4 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.20 e Å⁻³
2294 reflections	Δρ_min = −0.41 e Å⁻³
202 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.40233 (3)	0.2500	0.02879 (13)
C1	0.42670 (16)	−0.1813 (2)	0.09408 (16)	0.0418 (6)
C2	0.42072 (13)	−0.04024 (19)	0.08275 (14)	0.0314 (5)
C3	0.35591 (14)	0.0140 (2)	0.03319 (15)	0.0371 (6)
C4	0.34858 (15)	0.1436 (2)	0.02799 (15)	0.0422 (6)
H4A	0.3049	0.1798	−0.0061	0.051*
C5	0.40373 (14)	0.2213 (2)	0.07156 (14)	0.0376 (5)
H5A	0.3975	0.3106	0.0685	0.045*
C6	0.47632 (13)	0.03895 (19)	0.12562 (13)	0.0306 (5)
H6A	0.5204	0.0032	0.1593	0.037*
C7	0.46889 (13)	0.16841 (18)	0.12030 (13)	0.0281 (5)
C8	0.60516 (14)	0.2224 (2)	0.16257 (13)	0.0340 (5)
H8A	0.6237	0.1479	0.1343	0.041*
C9	0.66617 (13)	0.3041 (2)	0.20555 (14)	0.0333 (5)
C10	0.75249 (14)	0.2905 (2)	0.19473 (15)	0.0463 (6)
H10A	0.7747	0.2214	0.1629	0.056*
C11	0.80586 (17)	0.3784 (3)	0.23054 (17)	0.0543 (7)
H11A	0.8656	0.3711	0.2242	0.065*
C12	0.77113 (16)	0.4765 (3)	0.27551 (17)	0.0529 (7)
H12A	0.8067	0.5404	0.2989	0.064*
C13	0.68392 (16)	0.4830 (2)	0.28702 (16)	0.0445 (6)
H13A	0.6608	0.5500	0.3202	0.053*
N1	0.52662 (11)	0.25156 (15)	0.16309 (11)	0.0290 (4)
N2	0.63159 (11)	0.39730 (16)	0.25264 (11)	0.0347 (4)
O1	0.37216 (11)	−0.24708 (15)	0.05397 (12)	0.0591 (5)
O2	0.48289 (12)	−0.22398 (14)	0.14171 (12)	0.0561 (5)
O3	0.29873 (10)	−0.06080 (16)	−0.00716 (11)	0.0531 (5)
H3A	0.3095	−0.1370	0.0035	0.080*
O4	0.50698 (13)	0.53118 (16)	0.15316 (12)	0.0501 (5)
O5	0.62630 (14)	0.48046 (19)	0.02994 (14)	0.0614 (5)
H4B	0.4935 (15)	0.6066 (17)	0.1536 (18)	0.062 (9)*
H4C	0.5432 (14)	0.522 (2)	0.1140 (13)	0.055 (9)*
H5C	0.618 (2)	0.419 (2)	−0.0026 (18)	0.084 (11)*
H5B	0.6754 (14)	0.505 (3)	0.024 (2)	0.109 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0350 (2)	0.0170 (2)	0.0344 (2)	0.000	0.00107 (18)	0.000
C1	0.0476 (16)	0.0267 (13)	0.0512 (15)	−0.0005 (11)	0.0112 (13)	−0.0075 (12)
C2	0.0363 (13)	0.0238 (12)	0.0340 (12)	0.0022 (9)	0.0041 (10)	−0.0050 (10)
C3	0.0412 (14)	0.0343 (14)	0.0359 (12)	0.0005 (10)	0.0030 (11)	−0.0131 (10)
C4	0.0479 (15)	0.0378 (14)	0.0409 (13)	0.0117 (11)	−0.0143 (11)	−0.0048 (11)
C5	0.0493 (14)	0.0233 (12)	0.0402 (13)	0.0051 (10)	−0.0040 (11)	−0.0003 (10)
C6	0.0308 (13)	0.0253 (11)	0.0357 (13)	0.0038 (9)	0.0029 (10)	0.0004 (10)
C7	0.0325 (12)	0.0212 (11)	0.0306 (12)	0.0003 (9)	0.0036 (10)	−0.0048 (9)
C8	0.0411 (15)	0.0244 (12)	0.0364 (13)	0.0011 (10)	0.0046 (11)	0.0001 (10)
C9	0.0329 (13)	0.0308 (13)	0.0362 (13)	−0.0016 (9)	−0.0001 (11)	0.0065 (11)
C10	0.0385 (15)	0.0470 (16)	0.0534 (16)	−0.0012 (11)	0.0037 (12)	0.0096 (13)
C11	0.0358 (14)	0.0617 (19)	0.0654 (19)	−0.0079 (13)	−0.0070 (13)	0.0216 (15)
C12	0.0469 (17)	0.0557 (18)	0.0563 (17)	−0.0195 (14)	−0.0180 (13)	0.0137 (14)
C13	0.0522 (16)	0.0393 (15)	0.0419 (14)	−0.0103 (12)	−0.0117 (12)	0.0048 (12)
N1	0.0346 (11)	0.0211 (9)	0.0313 (10)	0.0009 (7)	−0.0002 (8)	0.0019 (8)
N2	0.0387 (10)	0.0290 (10)	0.0365 (10)	−0.0064 (8)	−0.0045 (9)	0.0039 (9)
O1	0.0604 (12)	0.0302 (10)	0.0869 (13)	−0.0087 (8)	−0.0029 (10)	−0.0191 (9)
O2	0.0731 (13)	0.0220 (9)	0.0731 (12)	0.0054 (8)	−0.0089 (10)	0.0025 (9)
O3	0.0497 (11)	0.0443 (10)	0.0654 (12)	−0.0009 (8)	−0.0160 (9)	−0.0216 (9)
O4	0.0730 (13)	0.0260 (10)	0.0512 (11)	0.0140 (9)	0.0232 (10)	0.0116 (8)
O5	0.0665 (15)	0.0488 (13)	0.0688 (14)	−0.0066 (11)	0.0228 (12)	−0.0147 (11)

Geometric parameters (Å, º) top

Ni1—O4	2.0380 (17)	C8—C9	1.456 (3)
Ni1—N2	2.0754 (18)	C8—H8A	0.9500
Ni1—N1	2.1347 (17)	C9—N2	1.345 (3)
C1—O2	1.241 (3)	C9—C10	1.378 (3)
C1—O1	1.271 (3)	C10—C11	1.372 (3)
C1—C2	1.504 (3)	C10—H10A	0.9500
C2—C6	1.384 (3)	C11—C12	1.367 (4)
C2—C3	1.404 (3)	C11—H11A	0.9500
C3—O3	1.354 (3)	C12—C13	1.388 (3)
C3—C4	1.377 (3)	C12—H12A	0.9500
C4—C5	1.376 (3)	C13—N2	1.337 (3)
C4—H4A	0.9500	C13—H13A	0.9500
C5—C7	1.395 (3)	O3—H3A	0.8400
C5—H5A	0.9500	O4—H4B	0.825 (16)
C6—C7	1.376 (3)	O4—H4C	0.843 (16)
C6—H6A	0.9500	O5—H5C	0.837 (17)
C7—N1	1.431 (3)	O5—H5B	0.823 (18)
C8—N1	1.276 (3)

O4ⁱ—Ni1—O4	96.16 (11)	C6—C7—C5	119.61 (19)
O4ⁱ—Ni1—N2	93.23 (8)	C6—C7—N1	121.90 (19)
O4—Ni1—N2	88.74 (7)	C5—C7—N1	118.48 (18)
O4ⁱ—Ni1—N2ⁱ	88.74 (7)	N1—C8—C9	119.7 (2)
O4—Ni1—N2ⁱ	93.23 (8)	N1—C8—H8A	120.2
N2—Ni1—N2ⁱ	177.06 (9)	C9—C8—H8A	120.2
O4ⁱ—Ni1—N1	168.85 (7)	N2—C9—C10	122.9 (2)
O4—Ni1—N1	90.93 (7)	N2—C9—C8	114.73 (19)
N2—Ni1—N1	78.29 (7)	C10—C9—C8	122.3 (2)
N2ⁱ—Ni1—N1	99.48 (7)	C11—C10—C9	119.0 (2)
O4ⁱ—Ni1—N1ⁱ	90.93 (7)	C11—C10—H10A	120.5
O4—Ni1—N1ⁱ	168.85 (7)	C9—C10—H10A	120.5
N2—Ni1—N1ⁱ	99.48 (6)	C12—C11—C10	118.5 (2)
N2ⁱ—Ni1—N1ⁱ	78.29 (7)	C12—C11—H11A	120.7
N1—Ni1—N1ⁱ	83.45 (9)	C10—C11—H11A	120.7
O2—C1—O1	125.4 (2)	C11—C12—C13	120.0 (2)
O2—C1—C2	118.4 (2)	C11—C12—H12A	120.0
O1—C1—C2	116.2 (2)	C13—C12—H12A	120.0
C6—C2—C3	118.72 (19)	N2—C13—C12	121.7 (2)
C6—C2—C1	120.2 (2)	N2—C13—H13A	119.1
C3—C2—C1	121.0 (2)	C12—C13—H13A	119.1
O3—C3—C4	119.8 (2)	C8—N1—C7	117.79 (18)
O3—C3—C2	120.2 (2)	C8—N1—Ni1	112.01 (14)
C4—C3—C2	120.0 (2)	C7—N1—Ni1	129.08 (13)
C5—C4—C3	120.8 (2)	C13—N2—C9	117.7 (2)
C5—C4—H4A	119.6	C13—N2—Ni1	127.38 (16)
C3—C4—H4A	119.6	C9—N2—Ni1	114.39 (14)
C4—C5—C7	119.7 (2)	C3—O3—H3A	109.5
C4—C5—H5A	120.2	Ni1—O4—H4B	129 (2)
C7—C5—H5A	120.2	Ni1—O4—H4C	120.0 (17)
C7—C6—C2	121.2 (2)	H4B—O4—H4C	107 (3)
C7—C6—H6A	119.4	H5C—O5—H5B	109 (3)
C2—C6—H6A	119.4

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.84	1.72	2.475 (2)	149
O4—H4B···O2ⁱⁱ	0.83 (2)	1.81 (2)	2.621 (2)	168 (3)
O4—H4C···O5	0.84 (2)	1.91 (2)	2.744 (3)	173 (2)
O5—H5B···O3ⁱⁱⁱ	0.82 (2)	2.05 (2)	2.870 (3)	178 (3)
O5—H5C···O1^iv	0.84 (2)	1.99 (2)	2.793 (3)	160 (3)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₉N₂O₃)₂(H₂O)₂]·2H₂O
M_r	613.22
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	173
a, b, c (Å)	15.7628 (6), 10.5672 (3), 15.6178 (6)
V (Å³)	2601.44 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.41 × 0.34 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.725, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	14975, 2294, 1599
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 0.89
No. of reflections	2294
No. of parameters	202
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)	0.20, −0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.84	1.72	2.475 (2)	149
O4—H4B···O2ⁱ	0.825 (16)	1.808 (18)	2.621 (2)	168 (3)
O4—H4C···O5	0.843 (16)	1.906 (17)	2.744 (3)	173 (2)
O5—H5B···O3ⁱⁱ	0.823 (18)	2.047 (19)	2.870 (3)	178 (3)
O5—H5C···O1ⁱⁱⁱ	0.837 (17)	1.99 (2)	2.793 (3)	160 (3)

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

Acknowledgements

This work was supported by the Ningbo Natural Science Foundation (grant No. 2010 A610060), the `Qianjiang Talent' Projects of Zhejiang Province (grant No. 2009R10032), the Ningbo University Foundation (grant No. XK1066), the Program for Innovative Research Team of Ningbo Novel Photoelectric Materials and Devices (grant No. 2009B21007) and the K. C. Wong Magna Fund in Ningbo University.

References

Ali, M. A., Mirza, A. H., Butcher, R. J. & Tarafder, M. T. H. (2002). Inorg. Biochem. 92, 141–148. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cukurovali, A., Yilmaz, I., Ozmen, H. & Ahmedzade, M. (2002). Transition Met. Chem. 27, 171–176. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M. & Yamin, B. M. (2002). Polyhedron, 21, 2547–2554. Web of Science CSD CrossRef CAS Google Scholar

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