Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis­(dimethyl sulfoxide)nickel(II)

Djedouani, A.; Boufas, S.; Bendaas, A.; Allain, M.; Bouet, G.

doi:10.1107/S1600536809034655

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1205-m1206

doi:10.1107/S1600536809034655

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Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis(dimethyl sulfoxide)nickel(II)

Amel Djedouani,^a Sihem Boufas,^b ^* Abderrahmen Bendaas,^a Magali Allain ^c and Gilles Bouet ^d

^aLaboratoire d'Electrochimie des Matériaux, Moléculaires et Complexes, Département de Génie des Procédés, Faculté des Science de l'Ingénieur, Université Farhet Abbas de Setif, DZ-19000 Sétif, Algeria, ^bUniversité 20 Aout 1955, Skikda, Algeria, ^cCIMM, CNRS UMR 6200, Faculté des Science, Angers Cedex, France, and ^dSONAS, EA 921, Université D'Angers, Faculté de Pharmacie, Angers Cedex, France
^*Correspondence e-mail: boufas_sihem@yahoo.fr

(Received 20 August 2009; accepted 28 August 2009; online 12 September 2009)

In the title compound, [Ni(C₈H₇O₄)₂{(CH₃)₂SO}₂], the Ni^II atom is located on a crystallographic centre of symmetry and has a distorted octahedral coordination geometry of type MO₆. The bidentate dehydroacetic acid (DHA) ligands occupy the equatorial plane of the complex in a trans configuration, and the dimethyl sulfoxide (DMSO) ligands are weakly coordinated through their O atoms in the axial positions.

Related literature

3-Acetyl-4-hydroxy-6-methyl-2-oxo-2H-pyran (dehydroacetic acid) (Arndt et al., 1936 ) is a versatile starting material for the synthesis of a wide variety of heterocyclic ring systems (Tan & Ang, 1988 ). It has been shown to possess modest antifungal properties, see: Rao et al. (1978 ). For natural fungicides possessing structures analogous to 5,6-dihydrodehydroacetic acid, see: Bartels-Keith (1960 ); Miyakado et al. (1982 ); Ayer et al. (1988 ). The complexes of DHA with copper and with several other transition metal cations are fungistatic, see: Rao et al. (1978). For the nickel–DHA complex, see: Casabò et al. (1987 ). The configuration of the complex molecule is similar to that found in [Zn(DHA)₂·2(DMSO) and Cd(DHA)₂·2(DMSO)] (Zucolotto Chalaça et al., 2002 ), [Cu(DHA)₂·2(DMSO)] (Djedouani et al., 2006 ) and bis(4,6-dibromo-2-formylphenolato-κ²O,O′)-bis(dimethyl sulfoxide)nickel(II) (Zhang et al., 2007 ). For Ni—O_DMSO distances in similar structures, see: Ma et al. (2003 ); Tahir et al. (2007 ); Zhang et al. (2007).

Experimental

Crystal data

[Ni(C₈H₇O₄)₂(C₂H₆OS)₂]
M_r = 549.24
Monoclinic, P 2₁ /c
a = 11.3850 (10) Å
b = 6.2833 (4) Å
c = 19.7434 (15) Å
β = 123.525 (6)°
V = 1177.40 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.902, T_max = 0.902
14084 measured reflections
2628 independent reflections
1962 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.11
2628 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O2	1.9849 (16)
Ni1—O3	2.0159 (15)
Ni1—O1	2.1255 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O4ⁱⁱ	0.96	2.55	3.384 (4)	145
C2—H2B⋯O4ⁱⁱ	0.96	2.53	3.370 (4)	146
C2—H2C⋯O2ⁱⁱⁱ	0.96	2.46	3.378 (4)	160
Symmetry codes: (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 1998 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034655/hg2559sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034655/hg2559Isup2.hkl

checkCIF report

Comment top

3-Acetyl-4-hydroxy-6-methyl-2-oxo-2H-pyran (dehydroacetic acid) (Arndt et al., 1936) is a versatile starting material for the synthesis of a wide variety of heterocyclic ring systems (Tan & Ang, 1988). It has been shown to possess modest antifungal properties (Rao et al., 1978). The importance of similar pyrones as potential fungicides is reinforced by the existence of several natural fungicides possessing structures analogous to 5,6-dihydrodehydroacetic acid, such as alternaric acid (Bartels-Keith, 1960), the podoblastins (Miyakado et al., 1982) and lachnelluloic acid (Ayer et al., 1988). Also, it has been shown that the complexes of DHA with copper and with several other transition metal cations are fungistatic (Rao et al., 1978). This has motivated our study of the structural characterization of complexes of dehydroacetic acid. The complex of DHA with nickel was previously reported by Casabò et al. (1987), but their characterization of the compound was based only on thermal and elemental analysis, and on IR and NMR spectroscopy.

We present here the crystal structure determination of the title complex, [Ni(DHA)₂.2(DMSO)], (I) (DMSO = dimethylsulfoxide). The nature of the title compound, (I), was established by an X-ray structure determination and is shown in Fig. 1

The Ni atom lies on a crystallographic centre of symmetry with the ligands bonded to nickel in an all-trans fashion. The configuration of the complex molecule is similar to that found in [Zn(DHA)₂. 2(DMSO); Cd(DHA)2.2(DMSO)] (Zucolotto Chalaça et al., 2002), [Cu(DHA)₂. 2(DMSO)] (Djedouani et al., 2006), with (DHA: dehydroacetic acid) and Bis(4,6-dibromo-2-formylphenolato-κ² O,O')-bis(dimethyl sulfoxide)nickel(II), [Ni(C₇H₃Br₂O₂)₂(C₂H₆OS)₂] (Zhang et al., 2007).

The coordination polyhedron around the Ni atom is a slightly distorted octahedron (Table 1), with the O atoms of the DMSO groups in axial positions; and the Ni—O_DMSO distance is in agreement with literature values: [2.1139 (12) Å - 1.9897 (13) Å (Tahir et al., 2007), 1.998 (3) Å - 2.105 (3) Å (Zhang et al. 2007), 2.030 (2) Å- 2.057 (2)Å (Ma et al., 2003)].

The orientation of the DMSO molecule can be described by the torsion angles O3—Ni—O1—S [43.32 (4) °] and O2—Ni—O1—S [-137.70 (4) °]. The packing of (I) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 2) which form a three-dimensional network (Fig. 2).

Related literature top

3-Acetyl-4-hydroxy-6-methyl-2-oxo-2H-pyran (dehydroacetic acid) (Arndt et al., 1936) is a versatile starting material for the synthesis of a wide variety of heterocyclic ring systems (Tan & Ang, 1988). It has been shown to possess modest antifungal properties, see: Rao et al. (1978). For natural fungicides possessing structures analogous to 5,6-dihydrodehydroacetic acid, see: Bartels-Keith (1960); Miyakado et al. (1982); Ayer et al. (1988). The complexes of DHA with copper and with several other transition metal cations are fungistatic, see: Rao et al. (1978). For the nickel–DHA complex, see: Casabò et al. (1987). The configuration of the complex molecule is similar to that found in [Zn(DHA)₂.2(DMSO) and Cd(DHA)2.2(DMSO)] (Zucolotto Chalaça et al., 2002), [Cu(DHA)₂.2(DMSO)] (Djedouani et al., 2006) and bis(4,6-dibromo-2-formylphenolato-κ²O,O')-bis(dimethyl sulfoxide)nickel(II) (Zhang et al., 2007). For Ni—O_DMSO distances in similar structures, see: Ma et al. (2003); Tahir et al. (2007); Zhang et al. (2007).

Experimental top

Compound (I) was prepared by the reaction of dehydroacetic acid with nickel (II) chloride hexahydrate in the presence of sodium acetate (Casabò et al. 1987). Crystals of (I) were grown by slow evaporation of a dimethylsulfoxide solution..

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I); Hydrogen atoms have been omitted for clarity.

Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis(dimethyl sulfoxide)nickel(II) top

Crystal data top

[Ni(C₈H₇O₄)₂(C₂H₆OS)₂]	F(000) = 572
M_r = 549.24	D_x = 1.549 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2190 reflections
a = 11.385 (1) Å	θ = 2.8–27.3°
b = 6.2833 (4) Å	µ = 1.05 mm⁻¹
c = 19.7434 (15) Å	T = 100 K
β = 123.525 (6)°	Plates, colourless
V = 1177.40 (16) Å³	0.25 × 0.15 × 0.1 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	2628 independent reflections
Radiation source: fine-focus sealed X-ray tube	1962 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→14
T_min = 0.902, T_max = 0.902	k = −8→7
14084 measured reflections	l = −25→25

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o² + 0.3428P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
2628 reflections	Δρ_max = 0.55 e Å⁻³
156 parameters	Δρ_min = −0.97 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (19)

Crystal data top

[Ni(C₈H₇O₄)₂(C₂H₆OS)₂]	V = 1177.40 (16) Å³
M_r = 549.24	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.385 (1) Å	µ = 1.05 mm⁻¹
b = 6.2833 (4) Å	T = 100 K
c = 19.7434 (15) Å	0.25 × 0.15 × 0.1 mm
β = 123.525 (6)°

Data collection top

Nonius KappaCCD diffractometer	2628 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1962 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.902	R_int = 0.071
14084 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.11	Δρ_max = 0.55 e Å⁻³
2628 reflections	Δρ_min = −0.97 e Å⁻³
156 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.

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

	x	y	z	U_iso*/U_eq
Ni1	0.5	0.5	0.5	0.02521 (16)
S1	0.75777 (6)	0.76611 (10)	0.53190 (4)	0.03283 (19)
O5	0.22643 (18)	0.1935 (3)	0.18093 (9)	0.0384 (4)
O1	0.62169 (17)	0.6626 (3)	0.46467 (10)	0.0387 (4)
O2	0.47029 (16)	0.2626 (3)	0.42577 (9)	0.0307 (4)
O3	0.32165 (16)	0.6292 (3)	0.40600 (9)	0.0316 (4)
O4	0.1020 (2)	0.4798 (3)	0.15900 (11)	0.0478 (5)
C6	0.2779 (2)	0.4022 (4)	0.29848 (13)	0.0252 (5)
C3	0.1192 (3)	0.7190 (4)	0.28219 (15)	0.0378 (6)
H3A	0.1101	0.8133	0.3173	0.057*
H3B	0.0368	0.631	0.2527	0.057*
H3C	0.1291	0.801	0.2446	0.057*
C10	0.3256 (3)	0.0457 (4)	0.23083 (15)	0.0317 (6)
C8	0.3859 (2)	0.2500 (4)	0.34964 (14)	0.0253 (5)
C9	0.3994 (2)	0.0651 (4)	0.31075 (14)	0.0296 (5)
H9	0.4616	−0.0426	0.3428	0.036*
C5	0.2474 (2)	0.5807 (4)	0.33237 (13)	0.0265 (5)
C2	0.7743 (3)	1.0036 (4)	0.48915 (18)	0.0469 (7)
H2A	0.7626	0.9718	0.4382	0.07*
H2B	0.8659	1.0642	0.5256	0.07*
H2C	0.7034	1.1033	0.4805	0.07*
C7	0.1958 (2)	0.3697 (4)	0.21184 (14)	0.0312 (6)
C4	0.3357 (3)	−0.1273 (5)	0.18287 (17)	0.0470 (7)
H4A	0.4053	−0.2289	0.2191	0.071*
H4B	0.3623	−0.0679	0.1484	0.071*
H4C	0.246	−0.1966	0.1501	0.071*
C1	0.8954 (3)	0.6199 (5)	0.53594 (19)	0.0526 (8)
H1A	0.8972	0.4776	0.5542	0.079*
H1B	0.9841	0.6879	0.573	0.079*
H1C	0.8792	0.6154	0.4828	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0190 (2)	0.0297 (3)	0.0197 (2)	0.00047 (17)	0.00610 (17)	−0.00322 (16)
S1	0.0280 (3)	0.0421 (4)	0.0247 (3)	−0.0061 (3)	0.0122 (3)	−0.0037 (3)
O5	0.0403 (10)	0.0450 (11)	0.0241 (9)	0.0070 (8)	0.0141 (8)	−0.0024 (7)
O1	0.0292 (9)	0.0534 (11)	0.0275 (9)	−0.0120 (8)	0.0119 (8)	−0.0051 (8)
O2	0.0245 (8)	0.0336 (9)	0.0212 (8)	0.0057 (7)	0.0046 (7)	−0.0021 (7)
O3	0.0257 (8)	0.0336 (10)	0.0260 (9)	0.0043 (7)	0.0083 (7)	−0.0040 (7)
O4	0.0461 (12)	0.0539 (12)	0.0237 (9)	0.0148 (10)	0.0068 (8)	0.0052 (8)
C6	0.0210 (11)	0.0284 (13)	0.0226 (11)	−0.0001 (10)	0.0099 (9)	0.0003 (9)
C3	0.0292 (13)	0.0375 (15)	0.0335 (13)	0.0092 (11)	0.0090 (11)	−0.0011 (11)
C10	0.0273 (13)	0.0352 (14)	0.0342 (13)	−0.0012 (11)	0.0179 (11)	−0.0038 (10)
C8	0.0209 (11)	0.0285 (12)	0.0255 (11)	−0.0034 (10)	0.0122 (9)	−0.0008 (9)
C9	0.0225 (12)	0.0309 (13)	0.0286 (13)	0.0003 (10)	0.0098 (10)	−0.0023 (10)
C5	0.0202 (11)	0.0286 (13)	0.0266 (12)	−0.0018 (10)	0.0104 (10)	0.0025 (9)
C2	0.0358 (15)	0.0372 (16)	0.0524 (17)	0.0002 (12)	0.0148 (13)	0.0047 (12)
C7	0.0292 (13)	0.0347 (14)	0.0264 (12)	0.0010 (11)	0.0132 (10)	0.0013 (10)
C4	0.0510 (17)	0.0524 (18)	0.0395 (15)	0.0046 (15)	0.0262 (14)	−0.0127 (13)
C1	0.0350 (15)	0.0460 (18)	0.0587 (19)	0.0043 (14)	0.0144 (14)	−0.0056 (14)

Geometric parameters (Å, º) top

Ni1—O2ⁱ	1.9849 (16)	C3—C5	1.507 (3)
Ni1—O2	1.9849 (16)	C3—H3A	0.96
Ni1—O3	2.0159 (15)	C3—H3B	0.96
Ni1—O3ⁱ	2.0159 (15)	C3—H3C	0.96
Ni1—O1ⁱ	2.1255 (18)	C10—C9	1.321 (3)
Ni1—O1	2.1255 (18)	C10—C4	1.487 (4)
S1—O1	1.5211 (17)	C8—C9	1.447 (3)
S1—C2	1.775 (3)	C9—H9	0.93
S1—C1	1.780 (3)	C2—H2A	0.96
O5—C10	1.371 (3)	C2—H2B	0.96
O5—C7	1.398 (3)	C2—H2C	0.96
O2—C8	1.262 (3)	C4—H4A	0.96
O3—C5	1.250 (3)	C4—H4B	0.96
O4—C7	1.215 (3)	C4—H4C	0.96
C6—C8	1.440 (3)	C1—H1A	0.96
C6—C7	1.441 (3)	C1—H1B	0.96
C6—C5	1.443 (3)	C1—H1C	0.96

O2ⁱ—Ni1—O2	180	C9—C10—C4	127.3 (2)
O2ⁱ—Ni1—O3	92.94 (6)	O5—C10—C4	111.1 (2)
O2—Ni1—O3	87.06 (6)	O2—C8—C6	125.9 (2)
O2ⁱ—Ni1—O3ⁱ	87.06 (6)	O2—C8—C9	116.6 (2)
O2—Ni1—O3ⁱ	92.94 (6)	C6—C8—C9	117.4 (2)
O3—Ni1—O3ⁱ	180.0000 (10)	C10—C9—C8	121.6 (2)
O2ⁱ—Ni1—O1ⁱ	89.72 (7)	C10—C9—H9	119.2
O2—Ni1—O1ⁱ	90.28 (7)	C8—C9—H9	119.2
O3—Ni1—O1ⁱ	89.31 (7)	O3—C5—C6	123.2 (2)
O3ⁱ—Ni1—O1ⁱ	90.69 (7)	O3—C5—C3	114.3 (2)
O2ⁱ—Ni1—O1	90.28 (7)	C6—C5—C3	122.51 (19)
O2—Ni1—O1	89.72 (7)	S1—C2—H2A	109.5
O3—Ni1—O1	90.69 (7)	S1—C2—H2B	109.5
O3ⁱ—Ni1—O1	89.31 (7)	H2A—C2—H2B	109.5
O1ⁱ—Ni1—O1	180	S1—C2—H2C	109.5
O1—S1—C2	105.60 (12)	H2A—C2—H2C	109.5
O1—S1—C1	105.41 (12)	H2B—C2—H2C	109.5
C2—S1—C1	97.65 (15)	O4—C7—O5	112.9 (2)
C10—O5—C7	121.85 (18)	O4—C7—C6	128.7 (2)
S1—O1—Ni1	116.97 (9)	O5—C7—C6	118.4 (2)
C8—O2—Ni1	129.32 (15)	C10—C4—H4A	109.5
C5—O3—Ni1	131.49 (15)	C10—C4—H4B	109.5
C8—C6—C7	118.8 (2)	H4A—C4—H4B	109.5
C8—C6—C5	121.45 (19)	C10—C4—H4C	109.5
C7—C6—C5	119.74 (19)	H4A—C4—H4C	109.5
C5—C3—H3A	109.5	H4B—C4—H4C	109.5
C5—C3—H3B	109.5	S1—C1—H1A	109.5
H3A—C3—H3B	109.5	S1—C1—H1B	109.5
C5—C3—H3C	109.5	H1A—C1—H1B	109.5
H3A—C3—H3C	109.5	S1—C1—H1C	109.5
H3B—C3—H3C	109.5	H1A—C1—H1C	109.5
C9—C10—O5	121.6 (2)	H1B—C1—H1C	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱⁱ	0.96	2.55	3.384 (4)	145
C2—H2B···O4ⁱⁱ	0.96	2.53	3.370 (4)	146
C2—H2C···O2ⁱⁱⁱ	0.96	2.46	3.378 (4)	160

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₇O₄)₂(C₂H₆OS)₂]
M_r	549.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.385 (1), 6.2833 (4), 19.7434 (15)
β (°)	123.525 (6)
V (Å³)	1177.40 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.25 × 0.15 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.902, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	14084, 2628, 1962
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.11
No. of reflections	2628
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.97

Computer programs: COLLECT (Nonius, 2002), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1998) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Selected bond lengths (Å) top

Ni1—O2ⁱ	1.9849 (16)	Ni1—O3ⁱ	2.0159 (15)
Ni1—O2	1.9849 (16)	Ni1—O1ⁱ	2.1255 (18)
Ni1—O3	2.0159 (15)	Ni1—O1	2.1255 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱⁱ	0.9600	2.5500	3.384 (4)	145.00
C2—H2B···O4ⁱⁱ	0.9600	2.5300	3.370 (4)	146.00
C2—H2C···O2ⁱⁱⁱ	0.9600	2.4600	3.378 (4)	160.00

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

Acknowledgements

This work was supported by Université Farhet Abbas de Sétif, Sétif, Algeria.

References

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Volume 65| Part 10| October 2009| Pages m1205-m1206

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis­­(di­methyl sulfoxide)nickel(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis(dimethyl sulfoxide)nickel(II)