Bis­(di­methyl sulfoxide-κO)­bis(1-phenyl­butane-1,3-dionato-κ²O,O′)­nickel(II)

In the reaction of bis(1-phenyl­butane-1,3-dionato)­nickel(II) with di­methyl sulfoxide, the adduct bis­(di­methyl sulfoxide)­bis(1-phenyl­butane-1,3-dionato)­nickel(II), [Ni(C₁₀H₉O₂)₂(C₂H₆OS)₂], is formed, in which two di­methyl sulfoxide (DMSO) mol­ecules are coordinated to the Ni atom through their O atoms in a trans arrangement. The compound crystallizes in space group P2₁/a with the Ni atom lying on a center of inversion. The coordination polyhedron around the Ni atom is a distorted octahedron. The chelate ring deviates slightly from planarity. The Ni—O bond distance to the DMSO O atom is slightly longer than that to the 1-phenyl­;butane-1,3-dionate ligand. In the crystal structure, two-dimensional frameworks are formed by C–H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.064
• Data-to-parameter ratio = 22.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C24 H30 Ni O6 S2

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

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST97 (Nardelli, 1995).

Bis(dimethyl sulfoxide-κO)bis(1-phenylbutane-1,3-dionate-κ²O,O')nickel(II)

Crystal data

[Ni(C10H9O2)2(C2H6OS)2]	F(000) = 564
Mr = 537.31	Dx = 1.489 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 5096 reflections
a = 7.3772 (17) Å	θ = 2.1–21.3°
b = 13.453 (2) Å	µ = 1.02 mm^−1
c = 12.085 (2) Å	T = 100 K
β = 92.026 (18)°	Block, green
V = 1198.7 (4) Å^3	0.30 × 0.14 × 0.10 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	3516 independent reflections
Radiation source: fine-focus sealed tube	2561 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 30.1°, θmin = 4.1°
Absorption correction: analytical (Alcock, 1970)	h = −10→10
Tmin = 0.818, Tmax = 0.912	k = −18→18
32533 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0219P)^2] where P = (Fo^2 + 2Fc^2)/3
3516 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni	−0.5000	0.0000	0.5000	0.01175 (9)
O12	−0.57523 (16)	−0.12538 (9)	0.57711 (10)	0.0143 (3)
O11	−0.42381 (16)	0.05995 (9)	0.64556 (10)	0.0142 (3)
O2	−0.23567 (17)	−0.05838 (9)	0.49094 (10)	0.0156 (3)
S2	−0.16864 (6)	−0.11127 (4)	0.38974 (4)	0.01535 (11)
C21	−0.0646 (3)	−0.01827 (14)	0.30905 (16)	0.0213 (5)
H21B	0.0288	0.0143	0.3529	0.032*
H21A	−0.1540	0.0296	0.2850	0.032*
H21C	−0.0123	−0.0485	0.2457	0.032*
C22	0.0312 (2)	−0.17378 (14)	0.43539 (16)	0.0183 (4)
H22C	−0.0001	−0.2295	0.4804	0.028*
H22B	0.1071	−0.1290	0.4781	0.028*
H22A	0.0952	−0.1967	0.3725	0.028*
C11	−0.6024 (3)	−0.24838 (14)	0.71412 (16)	0.0199 (4)
H11A	−0.6916	−0.2751	0.6626	0.030*
H11C	−0.6515	−0.2457	0.7866	0.030*
H11B	−0.4967	−0.2901	0.7159	0.030*
C12	−0.5510 (2)	−0.14487 (14)	0.67841 (16)	0.0150 (4)
C13	−0.4801 (2)	−0.07943 (14)	0.75847 (15)	0.0159 (4)
H13	−0.4732	−0.1019	0.8313	0.019*
C14	−0.4186 (2)	0.01675 (14)	0.73870 (14)	0.0132 (4)
C15	−0.3386 (2)	0.07743 (15)	0.83229 (15)	0.0150 (4)
C16	−0.2716 (3)	0.03618 (17)	0.93050 (16)	0.0263 (5)
H16	−0.2812	−0.0319	0.9423	0.032*
C17	−0.1906 (3)	0.09593 (19)	1.01094 (17)	0.0333 (6)
H17	−0.1454	0.0677	1.0765	0.040*
C18	−0.1761 (3)	0.19714 (18)	0.99491 (17)	0.0293 (5)
H18	−0.1213	0.2368	1.0495	0.035*
C19	−0.2425 (3)	0.23897 (16)	0.89860 (17)	0.0252 (5)
H19	−0.2337	0.3072	0.8875	0.030*
C110	−0.3227 (2)	0.17923 (15)	0.81806 (16)	0.0186 (4)
H110	−0.3671	0.2080	0.7526	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.01212 (16)	0.01274 (19)	0.01040 (17)	−0.00004 (15)	0.00074 (12)	−0.00066 (15)
O12	0.0155 (6)	0.0140 (7)	0.0136 (7)	−0.0005 (5)	0.0011 (5)	0.0002 (5)
O11	0.0173 (7)	0.0133 (7)	0.0120 (7)	0.0001 (6)	−0.0001 (5)	0.0010 (6)
O2	0.0134 (6)	0.0196 (8)	0.0140 (7)	0.0023 (6)	0.0009 (5)	−0.0039 (6)
S2	0.0122 (2)	0.0167 (3)	0.0172 (2)	0.0000 (2)	0.00126 (18)	−0.0035 (2)
C21	0.0193 (10)	0.0251 (13)	0.0197 (10)	0.0073 (9)	0.0041 (8)	0.0068 (9)
C22	0.0176 (10)	0.0152 (11)	0.0225 (11)	0.0041 (8)	0.0039 (8)	0.0031 (9)
C11	0.0205 (10)	0.0186 (11)	0.0206 (11)	−0.0015 (9)	0.0003 (8)	0.0033 (9)
C12	0.0099 (8)	0.0157 (11)	0.0196 (10)	0.0033 (8)	0.0032 (7)	0.0027 (8)
C13	0.0171 (9)	0.0174 (11)	0.0131 (10)	0.0013 (8)	0.0005 (7)	0.0032 (8)
C14	0.0084 (8)	0.0190 (12)	0.0124 (9)	0.0042 (8)	0.0013 (7)	−0.0014 (8)
C15	0.0118 (9)	0.0205 (11)	0.0129 (9)	−0.0002 (8)	0.0023 (7)	−0.0029 (8)
C16	0.0306 (12)	0.0291 (13)	0.0189 (11)	−0.0059 (10)	−0.0035 (9)	0.0031 (9)
C17	0.0363 (13)	0.0505 (17)	0.0125 (11)	−0.0073 (12)	−0.0068 (9)	0.0033 (10)
C18	0.0249 (11)	0.0438 (16)	0.0193 (11)	−0.0100 (11)	0.0016 (9)	−0.0132 (10)
C19	0.0231 (11)	0.0255 (13)	0.0272 (12)	−0.0041 (9)	0.0031 (9)	−0.0093 (10)
C110	0.0163 (9)	0.0229 (12)	0.0165 (10)	0.0010 (9)	−0.0003 (8)	−0.0032 (9)

Geometric parameters (Å, º)

Ni—O11	1.9978 (12)	C11—H11B	0.9600
Ni—O12	2.0145 (13)	C12—C13	1.396 (3)
Ni—O2	2.1087 (13)	C13—C14	1.394 (2)
O12—C12	1.259 (2)	C13—H13	0.9300
O11—C14	1.266 (2)	C14—C15	1.499 (2)
O2—S2	1.5131 (13)	C15—C16	1.385 (3)
S2—C22	1.7688 (18)	C15—C110	1.386 (3)
S2—C21	1.7772 (19)	C16—C17	1.381 (3)
C21—H21B	0.9600	C16—H16	0.9300
C21—H21A	0.9600	C17—C18	1.380 (3)
C21—H21C	0.9600	C17—H17	0.9300
C22—H22C	0.9600	C18—C19	1.368 (3)
C22—H22B	0.9600	C18—H18	0.9300
C22—H22A	0.9600	C19—C110	1.379 (3)
C11—C12	1.510 (3)	C19—H19	0.9300
C11—H11A	0.9600	C110—H110	0.9300
C11—H11C	0.9600
O11—Ni—O12	90.24 (5)	O12—C12—C13	125.43 (18)
O11—Ni—O2	87.95 (5)	O12—C12—C11	116.20 (17)
O12—Ni—O2	89.00 (5)	C13—C12—C11	118.37 (17)
C12—O12—Ni	126.33 (12)	C14—C13—C12	125.63 (17)
C14—O11—Ni	126.60 (12)	C14—C13—H13	117.2
S2—O2—Ni	123.12 (7)	C12—C13—H13	117.2
O2—S2—C22	105.31 (8)	O11—C14—C13	125.34 (16)
O2—S2—C21	105.80 (9)	O11—C14—C15	114.80 (16)
C22—S2—C21	97.72 (9)	C13—C14—C15	119.86 (16)
S2—C21—H21B	109.5	C16—C15—C110	118.23 (18)
S2—C21—H21A	109.5	C16—C15—C14	123.18 (18)
H21B—C21—H21A	109.5	C110—C15—C14	118.52 (16)
S2—C21—H21C	109.5	C17—C16—C15	120.1 (2)
H21B—C21—H21C	109.5	C17—C16—H16	119.9
H21A—C21—H21C	109.5	C15—C16—H16	119.9
S2—C22—H22C	109.5	C18—C17—C16	120.6 (2)
S2—C22—H22B	109.5	C18—C17—H17	119.7
H22C—C22—H22B	109.5	C16—C17—H17	119.7
S2—C22—H22A	109.5	C19—C18—C17	119.9 (2)
H22C—C22—H22A	109.5	C19—C18—H18	120.1
H22B—C22—H22A	109.5	C17—C18—H18	120.1
C12—C11—H11A	109.5	C18—C19—C110	119.5 (2)
C12—C11—H11C	109.5	C18—C19—H19	120.2
H11A—C11—H11C	109.5	C110—C19—H19	120.2
C12—C11—H11B	109.5	C19—C110—C15	121.63 (19)
H11A—C11—H11B	109.5	C19—C110—H110	119.2
H11C—C11—H11B	109.5	C15—C110—H110	119.2