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

In the title compound, [Fe(C(5)H(6)ClO(2))(3)], the Fe(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 a slightly distorted octa-hedral environment. Fe-O bond lengths are in the range 1.9818 (18)-1.9957 (18) Å. The trans O-Fe-O angles are 169.06 (13) and 171.54 (8)°, whereas the corresponding cis angles are in the range 84.81 (10)-100.68 (12)°. In the crystal, mol-ecules are linked via C-H⋯Cl inter-actions.

Related literature

For applications of metal complexes with β-diketonate ligands, see: Bray et al. (2007 ▶); Garibay et al. (2009 ▶); Perdih (2011 ▶); Schröder et al. (2011 ▶). For related structures, see: Iball & Morgan (1967 ▶); Perdih (2012 ▶); Pfluger & Haradem (1983 ▶).

Experimental

Crystal data

[Fe(C5H6ClO2)3]

M = 456.49

Monoclinic,

a = 15.7745 (4) Å

b = 9.5424 (2) Å

c = 12.9833 (3) Å

β = 100.610 (1)°

V = 1920.92 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.23 mm−1

T = 293 K

0.25 × 0.25 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.749, T max = 0.857

4155 measured reflections

2155 independent reflections

1927 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.07

2155 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.62 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023215/im2375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023215/im2375Isup2.hkl

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

[Fe(C5H6ClO2)3]	F(000) = 932
Mr = 456.49	Dx = 1.578 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2278 reflections
a = 15.7745 (4) Å	θ = 2.6–27.5°
b = 9.5424 (2) Å	µ = 1.23 mm−1
c = 12.9833 (3) Å	T = 293 K
β = 100.610 (1)°	Prism, red
V = 1920.92 (8) Å3	0.25 × 0.25 × 0.13 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	2155 independent reflections
Radiation source: fine-focus sealed tube	1927 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Detector resolution: 0.055 pixels mm-1	θmax = 27.4°, θmin = 3.9°
ω scans	h = −20→20
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.749, Tmax = 0.857	l = −16→16
4155 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0748P)2 + 1.6605P] where P = (Fo2 + 2Fc2)/3
2155 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Experimental. 192 frames in 5 sets of ω scans. Rotation/frame = 2.0 °. Crystal-detector distance = 25.00 mm. Measuring time = 60 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
Fe1	0.5	0.20825 (5)	0.75	0.04488 (18)
Cl1	0.20617 (6)	0.40123 (14)	0.58549 (12)	0.1198 (5)
Cl2	0.5	−0.33055 (10)	0.75	0.0684 (3)
O1	0.38591 (12)	0.2280 (2)	0.79173 (16)	0.0642 (5)
O2	0.45438 (12)	0.3417 (2)	0.63475 (15)	0.0593 (4)
O3	0.46568 (12)	0.05417 (17)	0.64737 (13)	0.0528 (4)
C1	0.2404 (2)	0.2638 (6)	0.7991 (4)	0.0987 (13)
H1A	0.261	0.2436	0.8718	0.148*
H1B	0.2042	0.1885	0.7677	0.148*
H1C	0.2077	0.3493	0.7928	0.148*
C2	0.31593 (17)	0.2797 (3)	0.7439 (3)	0.0622 (7)
C3	0.30871 (17)	0.3467 (3)	0.6477 (3)	0.0680 (8)
C4	0.37767 (19)	0.3776 (3)	0.5971 (2)	0.0613 (7)
C5	0.3663 (3)	0.4565 (4)	0.4949 (3)	0.0931 (12)
H5A	0.4217	0.4738	0.477	0.14*
H5B	0.338	0.5441	0.502	0.14*
H5C	0.3318	0.4018	0.4407	0.14*
C6	0.44210 (19)	−0.1585 (3)	0.5553 (2)	0.0621 (6)
H6A	0.4189	−0.0946	0.5001	0.093*
H6B	0.3986	−0.2251	0.5649	0.093*
H6C	0.4906	−0.207	0.5371	0.093*
C7	0.47040 (14)	−0.0786 (2)	0.65475 (17)	0.0450 (5)
C8	0.5	−0.1469 (3)	0.75	0.0458 (6)

	U11	U22	U33	U12	U13	U23
Fe1	0.0379 (3)	0.0458 (3)	0.0498 (3)	0	0.00487 (18)	0
Cl1	0.0618 (5)	0.1015 (7)	0.1759 (12)	0.0164 (5)	−0.0313 (6)	0.0217 (8)
Cl2	0.0768 (6)	0.0450 (5)	0.0797 (6)	0	0.0049 (5)	0
O1	0.0414 (9)	0.0889 (14)	0.0627 (11)	0.0061 (9)	0.0104 (8)	0.0053 (10)
O2	0.0604 (10)	0.0518 (10)	0.0645 (10)	0.0054 (8)	0.0086 (8)	0.0092 (8)
O3	0.0610 (10)	0.0481 (9)	0.0457 (8)	−0.0038 (7)	0.0005 (7)	0.0015 (7)
C1	0.0466 (17)	0.135 (4)	0.119 (3)	0.0057 (19)	0.0246 (18)	−0.012 (3)
C2	0.0405 (12)	0.0661 (16)	0.0778 (17)	0.0025 (11)	0.0050 (11)	−0.0189 (13)
C3	0.0476 (13)	0.0521 (14)	0.095 (2)	0.0087 (11)	−0.0113 (13)	−0.0039 (14)
C4	0.0675 (16)	0.0383 (11)	0.0687 (15)	0.0023 (10)	−0.0117 (12)	−0.0008 (11)
C5	0.115 (3)	0.0650 (19)	0.085 (2)	−0.0019 (19)	−0.019 (2)	0.0217 (17)
C6	0.0720 (17)	0.0623 (15)	0.0495 (13)	−0.0082 (13)	0.0049 (11)	−0.0076 (11)
C7	0.0369 (10)	0.0515 (12)	0.0462 (11)	−0.0034 (8)	0.0066 (8)	−0.0030 (9)
C8	0.0390 (14)	0.0463 (16)	0.0520 (16)	0	0.0079 (12)	0

Fe1—O1i	1.9818 (18)	C1—H1C	0.96
Fe1—O1	1.9818 (18)	C2—C3	1.388 (5)
Fe1—O3	1.9912 (17)	C3—C4	1.402 (4)
Fe1—O3i	1.9912 (17)	C4—C5	1.507 (4)
Fe1—O2i	1.9957 (18)	C5—H5A	0.96
Fe1—O2	1.9957 (18)	C5—H5B	0.96
Cl1—C3	1.749 (3)	C5—H5C	0.96
Cl2—C8	1.753 (3)	C6—C7	1.495 (3)
O1—C2	1.263 (3)	C6—H6A	0.96
O2—C4	1.266 (3)	C6—H6B	0.96
O3—C7	1.271 (3)	C6—H6C	0.96
C1—C2	1.507 (5)	C7—C8	1.400 (3)
C1—H1A	0.96	C8—C7i	1.400 (3)
C1—H1B	0.96
O1i—Fe1—O1	169.06 (13)	C3—C2—C1	122.2 (3)
O1i—Fe1—O3	92.07 (8)	C2—C3—C4	125.2 (2)
O1—Fe1—O3	96.00 (9)	C2—C3—Cl1	117.9 (2)
O1i—Fe1—O3i	96.00 (9)	C4—C3—Cl1	116.9 (2)
O1—Fe1—O3i	92.07 (8)	O2—C4—C3	122.1 (3)
O3—Fe1—O3i	84.81 (10)	O2—C4—C5	115.2 (3)
O1i—Fe1—O2i	85.63 (8)	C3—C4—C5	122.7 (3)
O1—Fe1—O2i	87.39 (8)	C4—C5—H5A	109.5
O3—Fe1—O2i	171.54 (8)	C4—C5—H5B	109.5
O3i—Fe1—O2i	87.33 (8)	H5A—C5—H5B	109.5
O1i—Fe1—O2	87.39 (8)	C4—C5—H5C	109.5
O1—Fe1—O2	85.63 (8)	H5A—C5—H5C	109.5
O3—Fe1—O2	87.33 (8)	H5B—C5—H5C	109.5
O3i—Fe1—O2	171.54 (8)	C7—C6—H6A	109.5
O2i—Fe1—O2	100.68 (12)	C7—C6—H6B	109.5
C2—O1—Fe1	131.2 (2)	H6A—C6—H6B	109.5
C4—O2—Fe1	130.47 (19)	C7—C6—H6C	109.5
C7—O3—Fe1	132.86 (15)	H6A—C6—H6C	109.5
C2—C1—H1A	109.5	H6B—C6—H6C	109.5
C2—C1—H1B	109.5	O3—C7—C8	122.4 (2)
H1A—C1—H1B	109.5	O3—C7—C6	116.0 (2)
C2—C1—H1C	109.5	C8—C7—C6	121.6 (2)
H1A—C1—H1C	109.5	C7—C8—C7i	124.5 (3)
H1B—C1—H1C	109.5	C7—C8—Cl2	117.75 (16)
O1—C2—C3	122.8 (3)	C7i—C8—Cl2	117.75 (16)
O1—C2—C1	115.0 (3)
O1i—Fe1—O1—C2	64.1 (3)	C1—C2—C3—C4	173.3 (3)
O3—Fe1—O1—C2	−73.3 (3)	O1—C2—C3—Cl1	175.1 (2)
O3i—Fe1—O1—C2	−158.3 (3)	C1—C2—C3—Cl1	−5.2 (4)
O2i—Fe1—O1—C2	114.5 (3)	Fe1—O2—C4—C3	13.5 (4)
O2—Fe1—O1—C2	13.6 (3)	Fe1—O2—C4—C5	−167.0 (2)
O1i—Fe1—O2—C4	170.7 (2)	C2—C3—C4—O2	2.2 (5)
O1—Fe1—O2—C4	−17.7 (2)	Cl1—C3—C4—O2	−179.3 (2)
O3—Fe1—O2—C4	78.5 (2)	C2—C3—C4—C5	−177.2 (3)
O2i—Fe1—O2—C4	−104.2 (2)	Cl1—C3—C4—C5	1.3 (4)
O1i—Fe1—O3—C7	93.7 (2)	Fe1—O3—C7—C8	4.1 (3)
O1—Fe1—O3—C7	−93.7 (2)	Fe1—O3—C7—C6	−176.07 (17)
O3i—Fe1—O3—C7	−2.14 (17)	O3—C7—C8—C7i	−2.01 (16)
O2—Fe1—O3—C7	−179.0 (2)	C6—C7—C8—C7i	178.2 (2)
Fe1—O1—C2—C3	−5.3 (4)	O3—C7—C8—Cl2	177.99 (16)
Fe1—O1—C2—C1	174.9 (2)	C6—C7—C8—Cl2	−1.8 (2)
O1—C2—C3—C4	−6.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cl1ii	0.96	2.78	3.642 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cl1i	0.96	2.78	3.642 (3)	150

Symmetry code: (i) .