Tris(3-chloro-pentane-2,4-dionato-κ(2)O,O')aluminium.

In the title compound, [Al(C(5)H(6)ClO(2))(3)], the Al(III) cation is situated on a twofold rotation axis and is coordinated by six O atoms from three 3-chloro-pentane-2,4-dionate ligands in an octa-hedral environment. Al-O bond lengths are in the range 1.8741 (14)-1.8772 (14) Å. In the crystal, mol-ecules are linked via C-H⋯Cl contacts.

Related literature

For applications of metal complexes with β-diketonate ligands, see: Bray et al. (2007 ▶); Garibay et al. (2009 ▶); Lichtenberger et al. (2010 ▶); Perdih (2011 ▶); Vreshch et al. (2004 ▶); Wu & Wang (2009 ▶). For related structures, see: Hon & Pfluger (1973 ▶); Perdih (2012 ▶).

Experimental

Crystal data

[Al(C5H6ClO2)3]

M = 427.62

Monoclinic,

a = 12.8790 (3) Å

b = 9.9086 (2) Å

c = 15.5311 (4) Å

β = 106.368 (2)°

V = 1901.64 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.33 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.838, T max = 0.957

3916 measured reflections

2156 independent reflections

1759 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.05

2156 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023203/im2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023203/im2374Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Al(C5H6ClO2)3]	F(000) = 880
Mr = 427.62	Dx = 1.494 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2269 reflections
a = 12.8790 (3) Å	θ = 2.6–27.5°
b = 9.9086 (2) Å	µ = 0.56 mm−1
c = 15.5311 (4) Å	T = 293 K
β = 106.368 (2)°	Plate, pink
V = 1901.64 (8) Å3	0.33 × 0.25 × 0.08 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	2156 independent reflections
Graphite monochromator	1759 reflections with I > 2σ(I)
Detector resolution: 0.055 pixels mm-1	Rint = 0.014
ω scans	θmax = 27.5°, θmin = 5.6°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −16→16
Tmin = 0.838, Tmax = 0.957	k = −10→12
3916 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0632P)2 + 1.1678P] where P = (Fo2 + 2Fc2)/3
2156 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. 211 frames in 5 sets of ω scans. Rotation/frame = 2.0 °. Crystal-detector distance = 25.00 mm. Measuring time = 55 s/°.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Al1	0.5	0.15245 (8)	0.25	0.0454 (2)
Cl1	0.36200 (7)	0.39260 (8)	−0.04272 (5)	0.0995 (3)
Cl2	0.5	−0.35153 (8)	0.25	0.0799 (3)
O1	0.39394 (11)	0.28432 (14)	0.20496 (10)	0.0575 (4)
O2	0.53620 (11)	0.15368 (15)	0.14118 (9)	0.0565 (4)
O3	0.39461 (10)	0.01885 (13)	0.20911 (9)	0.0527 (3)
C1	0.2712 (2)	0.4373 (3)	0.1141 (2)	0.0824 (8)
H1A	0.2095	0.4025	0.0694	0.124*
H1B	0.292	0.5223	0.0945	0.124*
H1C	0.2532	0.4496	0.1695	0.124*
C2	0.36336 (15)	0.33939 (18)	0.12819 (15)	0.0558 (5)
C3	0.41130 (17)	0.3110 (2)	0.06059 (14)	0.0587 (5)
C4	0.49653 (15)	0.2202 (2)	0.06969 (12)	0.0529 (4)
C5	0.5460 (2)	0.1956 (3)	−0.00518 (15)	0.0756 (7)
H5A	0.6094	0.1406	0.016	0.113*
H5B	0.5656	0.2803	−0.0262	0.113*
H5C	0.4947	0.1502	−0.0534	0.113*
C6	0.29806 (17)	−0.1843 (2)	0.17442 (17)	0.0671 (6)
H6A	0.2393	−0.1214	0.156	0.101*
H6B	0.2852	−0.2439	0.2191	0.101*
H6C	0.3034	−0.2359	0.1235	0.101*
C7	0.40167 (15)	−0.10871 (18)	0.21301 (11)	0.0468 (4)
C8	0.5	−0.1744 (3)	0.25	0.0493 (6)

	U11	U22	U33	U12	U13	U23
Al1	0.0412 (4)	0.0466 (4)	0.0457 (4)	0	0.0078 (3)	0
Cl1	0.1147 (6)	0.0930 (5)	0.0719 (4)	0.0188 (4)	−0.0043 (4)	0.0304 (3)
Cl2	0.0779 (6)	0.0479 (4)	0.0966 (6)	0	−0.0039 (4)	0
O1	0.0517 (7)	0.0531 (8)	0.0671 (8)	0.0097 (6)	0.0155 (6)	0.0005 (6)
O2	0.0512 (7)	0.0686 (8)	0.0482 (7)	0.0139 (6)	0.0116 (5)	0.0076 (6)
O3	0.0422 (6)	0.0522 (7)	0.0565 (7)	0.0005 (5)	0.0021 (5)	−0.0059 (6)
C1	0.0621 (13)	0.0577 (12)	0.114 (2)	0.0167 (11)	0.0029 (13)	−0.0025 (13)
C2	0.0430 (9)	0.0406 (9)	0.0739 (13)	−0.0008 (7)	0.0002 (8)	−0.0001 (8)
C3	0.0546 (11)	0.0536 (10)	0.0573 (11)	−0.0005 (9)	−0.0015 (8)	0.0105 (9)
C4	0.0461 (9)	0.0589 (10)	0.0483 (9)	−0.0071 (8)	0.0043 (7)	0.0034 (8)
C5	0.0700 (14)	0.1046 (19)	0.0528 (11)	0.0003 (14)	0.0182 (10)	0.0051 (12)
C6	0.0496 (11)	0.0674 (13)	0.0775 (14)	−0.0105 (10)	0.0066 (10)	−0.0102 (11)
C7	0.0457 (9)	0.0526 (10)	0.0400 (8)	−0.0046 (7)	0.0088 (7)	−0.0045 (7)
C8	0.0512 (14)	0.0484 (13)	0.0443 (12)	0	0.0072 (10)	0

Al1—O3	1.8741 (14)	C1—H1C	0.96
Al1—O3i	1.8741 (14)	C2—C3	1.389 (3)
Al1—O2i	1.8756 (13)	C3—C4	1.395 (3)
Al1—O2	1.8756 (13)	C4—C5	1.495 (3)
Al1—O1i	1.8772 (14)	C5—H5A	0.96
Al1—O1	1.8772 (14)	C5—H5B	0.96
Cl1—C3	1.748 (2)	C5—H5C	0.96
Cl2—C8	1.755 (3)	C6—C7	1.500 (3)
O1—C2	1.269 (3)	C6—H6A	0.96
O2—C4	1.268 (2)	C6—H6B	0.96
O3—C7	1.267 (2)	C6—H6C	0.96
C1—C2	1.500 (3)	C7—C8	1.396 (2)
C1—H1A	0.96	C8—C7i	1.396 (2)
C1—H1B	0.96
O3—Al1—O3i	90.12 (8)	C3—C2—C1	121.5 (2)
O3—Al1—O2i	88.26 (6)	C2—C3—C4	123.97 (18)
O3i—Al1—O2i	92.26 (6)	C2—C3—Cl1	118.44 (16)
O3—Al1—O2	92.26 (6)	C4—C3—Cl1	117.59 (17)
O3i—Al1—O2	88.26 (6)	O2—C4—C3	122.35 (18)
O2i—Al1—O2	179.26 (10)	O2—C4—C5	116.20 (19)
O3—Al1—O1i	178.02 (6)	C3—C4—C5	121.44 (19)
O3i—Al1—O1i	89.08 (6)	C4—C5—H5A	109.5
O2i—Al1—O1i	89.96 (6)	C4—C5—H5B	109.5
O2—Al1—O1i	89.53 (7)	H5A—C5—H5B	109.5
O3—Al1—O1	89.08 (6)	C4—C5—H5C	109.5
O3i—Al1—O1	178.02 (6)	H5A—C5—H5C	109.5
O2i—Al1—O1	89.53 (7)	H5B—C5—H5C	109.5
O2—Al1—O1	89.96 (6)	C7—C6—H6A	109.5
O1i—Al1—O1	91.78 (9)	C7—C6—H6B	109.5
C2—O1—Al1	130.55 (13)	H6A—C6—H6B	109.5
C4—O2—Al1	130.63 (13)	C7—C6—H6C	109.5
C7—O3—Al1	130.76 (12)	H6A—C6—H6C	109.5
C2—C1—H1A	109.5	H6B—C6—H6C	109.5
C2—C1—H1B	109.5	O3—C7—C8	121.98 (17)
H1A—C1—H1B	109.5	O3—C7—C6	115.78 (17)
C2—C1—H1C	109.5	C8—C7—C6	122.24 (19)
H1A—C1—H1C	109.5	C7i—C8—C7	124.4 (2)
H1B—C1—H1C	109.5	C7i—C8—Cl2	117.82 (12)
O1—C2—C3	122.47 (17)	C7—C8—Cl2	117.82 (12)
O1—C2—C1	116.0 (2)
O3—Al1—O1—C2	−89.43 (17)	C1—C2—C3—C4	−179.5 (2)
O2i—Al1—O1—C2	−177.70 (17)	O1—C2—C3—Cl1	179.76 (15)
O2—Al1—O1—C2	2.83 (18)	C1—C2—C3—Cl1	0.1 (3)
O1i—Al1—O1—C2	92.36 (17)	Al1—O2—C4—C3	−0.2 (3)
O3—Al1—O2—C4	87.74 (18)	Al1—O2—C4—C5	179.99 (15)
O3i—Al1—O2—C4	177.79 (18)	C2—C3—C4—O2	1.3 (3)
O1i—Al1—O2—C4	−93.12 (18)	Cl1—C3—C4—O2	−178.31 (15)
O1—Al1—O2—C4	−1.34 (18)	C2—C3—C4—C5	−179.0 (2)
O3i—Al1—O3—C7	1.05 (13)	Cl1—C3—C4—C5	1.4 (3)
O2i—Al1—O3—C7	−91.21 (17)	Al1—O3—C7—C8	−2.0 (3)
O2—Al1—O3—C7	89.32 (16)	Al1—O3—C7—C6	178.65 (13)
O1—Al1—O3—C7	179.24 (16)	O3—C7—C8—C7i	1.01 (12)
Al1—O1—C2—C3	−2.7 (3)	C6—C7—C8—C7i	−179.72 (19)
Al1—O1—C2—C1	176.98 (15)	O3—C7—C8—Cl2	−178.99 (12)
O1—C2—C3—C4	0.2 (3)	C6—C7—C8—Cl2	0.28 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cl1ii	0.96	2.94	3.796 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cl1i	0.96	2.94	3.796 (2)	149

Symmetry code: (i) .