Bis[μ-1,1′-(ferrocene-1,1′-di­yl)bis(butane-1,3-dionato)]di-μ-methanol-diiron(II)

Xiao, Y.-F.; Li, H.-F.; Yan, P.-F.; Li, G.-M.

doi:10.1107/S1600536809016353

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m624

doi:10.1107/S1600536809016353

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Bis[μ-1,1′-(ferrocene-1,1′-diyl)bis(butane-1,3-dionato)]di-μ-methanol-diiron(II)

Yan-Feng Xiao,^a Hong-Feng Li,^a Peng-Fei Yan ^a and Guang-Ming Li ^a ^*

^aKey Laboratory of Functional Inorganic Material Chemistry (Heilongjiang University), Ministry of Education, School of Chemistry and Materials Science, Heilongjiang University, 74 Xuefu Road, Nangang District, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 31 March 2009; accepted 30 April 2009; online 7 May 2009)

The asymmetric unit of the title compound, [Fe₄(C₉H₈O₂)₄(CH₃OH)₂], contains one half-molecule located on a twofold rotational axis. In the molecule, the two Fe^II ions bridged by two coordinating methanol molecules are separated by 3.1286 (7) Å. Two crystallographically independent methanol molecules are situated on a twofold rotational axis; all attached H atoms are rotationally disordered between two equal orientations.

Related literature

For the similar cobalt and manganese complexes of the same beta-diketone, see: Yan et al. (2007 ).

Experimental

Crystal data

[Fe₄(C₉H₈O₂)₄(CH₄O)₂]
M_r = 880.10
Orthorhombic, A b a 2
a = 14.599 (3) Å
b = 19.290 (4) Å
c = 12.955 (3) Å
V = 3648.5 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 291 K
0.25 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.685, T_max = 0.737
16837 measured reflections
4079 independent reflections
3473 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.069
S = 1.05
4079 reflections
242 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1899 Friedel pairs
Flack parameter: −0.001 (16)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016353/cv2543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016353/cv2543Isup2.hkl

checkCIF report

Comment top

Recently, the cobalt and manganese complexes of the specific beta-diketone were published by Yan et al. (2007). Herewith we present the crystal structure of the title Fe^II complex with the same ligand, (I),

In (I) (Fig. 1), the tetradentate ferrocene-containing bis-beta-diketones ligand links Fe atoms into a complex through four O atoms of the two beta-diketone from two ligands. The two Fe^II ions and two 1,1'-bis(acetoacetyl)ferrocenes are bridged by two methanols molecules, dividing this macrocyclic framework into two small cyclic subunits.The four atoms - C19, C20, O5 and O6 - of the two methanol molecules lie on a twofold axis.

Related literature top

For the similar cobalt and manganese complexes of the same beta-diketone, see: Yan et al. (2007).

Experimental top

The title complex was obtained by the treatment of iron(II) chloride tetrahydrate (0.5 mmol, 0.099 g) with 1,1'-bis(acetoacetyl)ferrocene (0.5 mmol, 0.177 g) in methanol. The first two reactants were stirred for 12 h. The resulting precipitates were filtered, washed with methanol several times and dried; The deep red crystals were grown by slow evaporation of methanol. Single crystals were obtained after several weeks. Analysis calculated for C₃₈H₃₈Fe₄O₁₀: C, 51.98; H, 4.36; found: C, 50.83; H, 4.02%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 66% probability displacement ellipsoids. Unlabelled atoms are related to labelled atoms by the symmetry code (-x, 2 - y, z). H atoms omitted for clarity.

Bis[µ-1,1'-(Ferrocene-1,1'-diyl)bis(butane-1,3-dionato)]di-µ-methanol- diiron(II) top

Crystal data top

[Fe₄(C₉H₈O₂)₄(CH₄O)₂]	F(000) = 1808
M_r = 880.10	D_x = 1.602 Mg m⁻³
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 13899 reflections
a = 14.599 (3) Å	θ = 3.2–27.5°
b = 19.290 (4) Å	µ = 1.62 mm⁻¹
c = 12.955 (3) Å	T = 291 K
V = 3648.5 (13) Å³	Block, colourless
Z = 4	0.25 × 0.22 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4079 independent reflections
Radiation source: fine-focus sealed tube	3473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→18
T_min = 0.685, T_max = 0.737	k = −24→24
16837 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0338P)² + 0.1021P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.069	(Δ/σ)_max = 0.002
S = 1.05	Δρ_max = 0.24 e Å⁻³
4079 reflections	Δρ_min = −0.28 e Å⁻³
242 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.00077 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1899 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.001 (16)

Crystal data top

[Fe₄(C₉H₈O₂)₄(CH₄O)₂]	V = 3648.5 (13) Å³
M_r = 880.10	Z = 4
Orthorhombic, Aba2	Mo Kα radiation
a = 14.599 (3) Å	µ = 1.62 mm⁻¹
b = 19.290 (4) Å	T = 291 K
c = 12.955 (3) Å	0.25 × 0.22 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4079 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3473 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.737	R_int = 0.042
16837 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.069	Δρ_max = 0.24 e Å⁻³
S = 1.05	Δρ_min = −0.28 e Å⁻³
4079 reflections	Absolute structure: Flack (1983), 1899 Friedel pairs
242 parameters	Absolute structure parameter: −0.001 (16)
13 restraints

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.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.19291 (19)	0.81289 (13)	0.8190 (2)	0.0354 (7)
C2	0.26358 (18)	0.76630 (12)	0.7841 (4)	0.0447 (7)
H2	0.2613	0.7380	0.7213	0.054*
C3	0.3373 (2)	0.76887 (17)	0.8546 (3)	0.0512 (9)
H3	0.3945	0.7425	0.8498	0.061*
C4	0.3135 (2)	0.81604 (17)	0.9337 (3)	0.0506 (8)
H4	0.3518	0.8282	0.9931	0.061*
C5	0.2264 (2)	0.84401 (15)	0.9114 (2)	0.0407 (7)
H5	0.1938	0.8784	0.9533	0.049*
C6	0.3017 (2)	0.93295 (15)	0.6728 (2)	0.0423 (7)
H6	0.2494	0.9363	0.6257	0.051*
C7	0.3795 (2)	0.88989 (17)	0.6594 (3)	0.0504 (8)
H7	0.3905	0.8584	0.6013	0.060*
C8	0.4386 (2)	0.90046 (18)	0.7442 (3)	0.0534 (9)
H8	0.4974	0.8772	0.7553	0.064*
C9	0.39808 (19)	0.94907 (15)	0.8111 (3)	0.0445 (8)
H9	0.4241	0.9658	0.8763	0.053*
C10	0.31223 (18)	0.96990 (14)	0.7674 (2)	0.0345 (7)
C11	0.10328 (17)	0.83008 (12)	0.7745 (2)	0.0330 (7)
C12	0.0715 (2)	0.79896 (15)	0.6841 (2)	0.0374 (7)
H12	0.1085	0.7663	0.6518	0.045*
C13	−0.0128 (2)	0.81460 (14)	0.6404 (2)	0.0360 (6)
C14	−0.0418 (2)	0.77915 (17)	0.5423 (3)	0.0506 (8)
H14A	−0.1028	0.7613	0.5503	0.076*
H14B	−0.0005	0.7417	0.5276	0.076*
H14C	−0.0406	0.8118	0.4864	0.076*
C15	0.24318 (18)	1.01769 (12)	0.8099 (2)	0.0318 (7)
C16	0.2553 (2)	1.04853 (15)	0.9063 (3)	0.0444 (7)
H16	0.3070	1.0368	0.9445	0.053*
C17	0.1943 (2)	1.09561 (14)	0.9477 (2)	0.0387 (7)
C18	0.2130 (3)	1.12866 (18)	1.0513 (3)	0.0588 (10)
H18A	0.2171	1.1780	1.0432	0.088*
H18B	0.2696	1.1112	1.0785	0.088*
H18C	0.1640	1.1178	1.0980	0.088*
C19	0.0000	1.0000	0.5883 (5)	0.087 (2)
H19A	−0.0225	1.0437	0.5636	0.130*	0.50
H19B	−0.0388	0.9634	0.5636	0.130*	0.50
H19C	0.0613	0.9929	0.5636	0.130*	0.50
C20	0.0000	1.0000	0.9899 (4)	0.078 (2)
H20A	−0.0137	0.9542	1.0146	0.117*	0.50
H20B	−0.0455	1.0319	1.0146	0.117*	0.50
H20C	0.0592	1.0139	1.0146	0.117*	0.50
Fe1	−0.05321 (2)	0.929603 (15)	0.78857 (4)	0.02974 (10)
Fe2	0.31370 (2)	0.865393 (17)	0.79403 (4)	0.03331 (10)
O1	0.05773 (13)	0.87374 (10)	0.82598 (15)	0.0409 (5)
O2	−0.06968 (14)	0.85889 (10)	0.67618 (17)	0.0406 (5)
O3	0.17416 (13)	1.02878 (10)	0.75155 (16)	0.0367 (5)
O4	0.11978 (14)	1.11480 (9)	0.90521 (16)	0.0382 (5)
O5	0.0000	1.0000	0.6928 (2)	0.0346 (7)
H20	−0.0100	1.0397	0.7126	0.052*	0.50
O6	0.0000	1.0000	0.8820 (2)	0.0319 (7)
H21	0.0530	1.0026	0.8623	0.048*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0409 (16)	0.0301 (12)	0.0351 (19)	0.0054 (11)	0.0030 (11)	0.0041 (12)
C2	0.0463 (15)	0.0309 (12)	0.0568 (18)	0.0085 (10)	0.004 (2)	−0.0019 (19)
C3	0.0468 (19)	0.0421 (17)	0.065 (2)	0.0151 (15)	−0.0060 (17)	0.0099 (17)
C4	0.055 (2)	0.059 (2)	0.0379 (18)	0.0072 (16)	−0.0096 (15)	0.0118 (16)
C5	0.0437 (18)	0.0459 (17)	0.0327 (15)	0.0087 (13)	−0.0019 (13)	0.0055 (14)
C6	0.0486 (19)	0.0465 (17)	0.0320 (16)	0.0059 (13)	0.0039 (14)	0.0056 (14)
C7	0.056 (2)	0.0577 (19)	0.0376 (17)	0.0114 (16)	0.0106 (15)	−0.0005 (16)
C8	0.0356 (17)	0.058 (2)	0.066 (2)	0.0113 (15)	0.0113 (16)	0.0046 (18)
C9	0.0336 (14)	0.0454 (15)	0.055 (3)	0.0009 (12)	−0.0060 (14)	−0.0036 (16)
C10	0.0340 (14)	0.0336 (13)	0.036 (2)	0.0000 (10)	−0.0001 (12)	0.0033 (12)
C11	0.0377 (14)	0.0269 (11)	0.0345 (18)	−0.0003 (10)	0.0080 (13)	−0.0012 (13)
C12	0.0381 (16)	0.0370 (15)	0.0371 (16)	0.0054 (12)	0.0066 (13)	−0.0091 (13)
C13	0.0421 (17)	0.0307 (13)	0.0352 (15)	−0.0099 (12)	0.0066 (13)	−0.0059 (12)
C14	0.049 (2)	0.055 (2)	0.0480 (19)	−0.0067 (15)	0.0030 (15)	−0.0194 (17)
C15	0.0344 (14)	0.0265 (11)	0.0347 (19)	−0.0048 (9)	−0.0053 (12)	0.0027 (12)
C16	0.0420 (17)	0.0434 (15)	0.0479 (19)	0.0061 (13)	−0.0190 (15)	−0.0071 (16)
C17	0.0453 (18)	0.0296 (14)	0.0412 (17)	−0.0037 (12)	−0.0112 (14)	−0.0044 (13)
C18	0.066 (2)	0.061 (2)	0.0492 (19)	0.0117 (16)	−0.023 (2)	−0.0177 (18)
C19	0.146 (7)	0.085 (4)	0.030 (3)	−0.044 (4)	0.000	0.000
C20	0.103 (5)	0.102 (5)	0.028 (3)	−0.047 (4)	0.000	0.000
Fe1	0.03050 (18)	0.02938 (16)	0.02933 (18)	−0.00004 (12)	0.0040 (2)	−0.0034 (2)
Fe2	0.03464 (19)	0.03372 (17)	0.03157 (19)	0.00768 (13)	−0.0017 (3)	−0.0015 (2)
O1	0.0402 (11)	0.0450 (11)	0.0374 (11)	0.0151 (9)	−0.0024 (8)	−0.0119 (9)
O2	0.0365 (12)	0.0411 (11)	0.0442 (12)	0.0003 (9)	−0.0024 (10)	−0.0119 (10)
O3	0.0345 (11)	0.0389 (10)	0.0366 (10)	0.0042 (8)	−0.0050 (8)	−0.0024 (9)
O4	0.0397 (12)	0.0296 (10)	0.0452 (12)	0.0028 (9)	−0.0111 (10)	−0.0053 (9)
O5	0.038 (2)	0.0422 (18)	0.0235 (15)	−0.0045 (14)	0.000	0.000
O6	0.042 (2)	0.0326 (16)	0.0215 (14)	−0.0051 (13)	0.000	0.000

Geometric parameters (Å, º) top

C1—C5	1.426 (4)	C13—O2	1.279 (3)
C1—C2	1.441 (4)	C13—C14	1.503 (4)
C1—C11	1.468 (4)	C14—H14A	0.9600
C1—Fe2	2.059 (3)	C14—H14B	0.9600
C2—C3	1.412 (5)	C14—H14C	0.9600
C2—Fe2	2.051 (3)	C15—O3	1.278 (3)
C2—H2	0.9800	C15—C16	1.394 (4)
C3—C4	1.413 (5)	C16—C17	1.381 (4)
C3—Fe2	2.050 (3)	C16—H16	0.9300
C3—H3	0.9800	C17—O4	1.274 (3)
C4—C5	1.412 (4)	C17—C18	1.511 (4)
C4—Fe2	2.044 (3)	C18—H18A	0.9600
C4—H4	0.9800	C18—H18B	0.9600
C5—Fe2	2.027 (3)	C18—H18C	0.9600
C5—H5	0.9800	C19—O5	1.355 (7)
C6—C7	1.418 (4)	C19—H19A	0.9600
C6—C10	1.426 (4)	C19—H19B	0.9600
C6—Fe2	2.048 (3)	C19—H19C	0.9600
C6—H6	0.9800	C20—O6	1.398 (6)
C7—C8	1.412 (5)	C20—H20A	0.9600
C7—Fe2	2.047 (3)	C20—H20B	0.9600
C7—H7	0.9800	C20—H20C	0.9600
C8—C9	1.407 (4)	Fe1—O6	1.9783 (17)
C8—Fe2	2.049 (3)	Fe1—O4ⁱ	1.991 (2)
C8—H8	0.9800	Fe1—O5	1.9964 (18)
C9—C10	1.433 (4)	Fe1—O3ⁱ	1.9982 (19)
C9—Fe2	2.043 (3)	Fe1—O1	2.0048 (19)
C9—H9	0.9800	Fe1—O2	2.010 (2)
C10—C15	1.473 (4)	O3—Fe1ⁱ	1.9982 (19)
C10—Fe2	2.045 (3)	O4—Fe1ⁱ	1.991 (2)
C11—O1	1.263 (3)	O5—Fe1ⁱ	1.9964 (18)
C11—C12	1.395 (4)	O5—H20	0.8211
C12—C13	1.389 (4)	O6—Fe1ⁱ	1.9783 (17)
C12—H12	0.9300	O6—H21	0.8158

C5—C1—C2	106.3 (3)	H18B—C18—H18C	109.5
C5—C1—C11	122.7 (2)	O5—C19—H19A	109.5
C2—C1—C11	131.0 (3)	O5—C19—H19B	109.5
C5—C1—Fe2	68.37 (17)	H19A—C19—H19B	109.5
C2—C1—Fe2	69.16 (15)	O5—C19—H19C	109.5
C11—C1—Fe2	126.20 (18)	H19A—C19—H19C	109.5
C3—C2—C1	108.7 (3)	H19B—C19—H19C	109.5
C3—C2—Fe2	69.82 (18)	O6—C20—H20A	109.5
C1—C2—Fe2	69.79 (15)	O6—C20—H20B	109.5
C3—C2—H2	125.6	H20A—C20—H20B	109.5
C1—C2—H2	125.6	O6—C20—H20C	109.5
Fe2—C2—H2	125.6	H20A—C20—H20C	109.5
C2—C3—C4	107.7 (3)	H20B—C20—H20C	109.5
C2—C3—Fe2	69.89 (16)	O6—Fe1—O4ⁱ	91.29 (9)
C4—C3—Fe2	69.60 (18)	O6—Fe1—O5	76.14 (7)
C2—C3—H3	126.1	O4ⁱ—Fe1—O5	162.62 (7)
C4—C3—H3	126.1	O6—Fe1—O3ⁱ	102.60 (6)
Fe2—C3—H3	126.1	O4ⁱ—Fe1—O3ⁱ	85.61 (8)
C5—C4—C3	108.6 (3)	O5—Fe1—O3ⁱ	85.50 (6)
C5—C4—Fe2	69.05 (18)	O6—Fe1—O1	84.48 (6)
C3—C4—Fe2	70.0 (2)	O4ⁱ—Fe1—O1	88.83 (9)
C5—C4—H4	125.7	O5—Fe1—O1	101.62 (6)
C3—C4—H4	125.7	O3ⁱ—Fe1—O1	171.08 (8)
Fe2—C4—H4	125.7	O6—Fe1—O2	163.02 (7)
C4—C5—C1	108.6 (3)	O4ⁱ—Fe1—O2	101.51 (8)
C4—C5—Fe2	70.37 (19)	O5—Fe1—O2	93.34 (9)
C1—C5—Fe2	70.80 (17)	O3ⁱ—Fe1—O2	89.60 (8)
C4—C5—H5	125.7	O1—Fe1—O2	84.66 (8)
C1—C5—H5	125.7	C5—Fe2—C9	117.30 (13)
Fe2—C5—H5	125.7	C5—Fe2—C4	40.58 (12)
C7—C6—C10	108.2 (3)	C9—Fe2—C4	105.82 (14)
C7—C6—Fe2	69.68 (18)	C5—Fe2—C10	108.69 (11)
C10—C6—Fe2	69.52 (17)	C9—Fe2—C10	41.04 (11)
C7—C6—H6	125.9	C4—Fe2—C10	127.46 (13)
C10—C6—H6	125.9	C5—Fe2—C7	169.03 (13)
Fe2—C6—H6	125.9	C9—Fe2—C7	68.09 (14)
C8—C7—C6	108.0 (3)	C4—Fe2—C7	149.56 (14)
C8—C7—Fe2	69.91 (19)	C10—Fe2—C7	68.51 (12)
C6—C7—Fe2	69.78 (18)	C5—Fe2—C6	130.60 (12)
C8—C7—H7	126.0	C9—Fe2—C6	68.41 (14)
C6—C7—H7	126.0	C4—Fe2—C6	167.07 (13)
Fe2—C7—H7	126.0	C10—Fe2—C6	40.77 (12)
C9—C8—C7	108.6 (3)	C7—Fe2—C6	40.54 (12)
C9—C8—Fe2	69.65 (17)	C5—Fe2—C8	149.67 (14)
C7—C8—Fe2	69.76 (19)	C9—Fe2—C8	40.23 (13)
C9—C8—H8	125.7	C4—Fe2—C8	115.68 (15)
C7—C8—H8	125.7	C10—Fe2—C8	68.34 (12)
Fe2—C8—H8	125.7	C7—Fe2—C8	40.33 (14)
C8—C9—C10	108.1 (3)	C6—Fe2—C8	67.97 (14)
C8—C9—Fe2	70.11 (18)	C5—Fe2—C3	68.49 (13)
C10—C9—Fe2	69.58 (15)	C9—Fe2—C3	125.10 (14)
C8—C9—H9	125.9	C4—Fe2—C3	40.38 (14)
C10—C9—H9	125.9	C10—Fe2—C3	164.08 (13)
Fe2—C9—H9	125.9	C7—Fe2—C3	117.22 (14)
C6—C10—C9	107.1 (3)	C6—Fe2—C3	152.39 (14)
C6—C10—C15	124.1 (3)	C8—Fe2—C3	105.73 (14)
C9—C10—C15	128.8 (3)	C5—Fe2—C2	68.45 (15)
C6—C10—Fe2	69.71 (16)	C9—Fe2—C2	163.45 (11)
C9—C10—Fe2	69.37 (16)	C4—Fe2—C2	67.72 (17)
C15—C10—Fe2	124.13 (18)	C10—Fe2—C2	154.74 (12)
O1—C11—C12	123.7 (2)	C7—Fe2—C2	109.24 (16)
O1—C11—C1	114.4 (2)	C6—Fe2—C2	120.98 (16)
C12—C11—C1	121.9 (2)	C8—Fe2—C2	127.27 (13)
C13—C12—C11	123.0 (2)	C3—Fe2—C2	40.29 (14)
C13—C12—H12	118.5	C5—Fe2—C1	40.83 (11)
C11—C12—H12	118.5	C9—Fe2—C1	152.63 (12)
O2—C13—C12	124.9 (3)	C4—Fe2—C1	68.34 (12)
O2—C13—C14	115.3 (3)	C10—Fe2—C1	120.15 (10)
C12—C13—C14	119.7 (3)	C7—Fe2—C1	130.52 (13)
C13—C14—H14A	109.5	C6—Fe2—C1	111.11 (12)
C13—C14—H14B	109.5	C8—Fe2—C1	166.90 (13)
H14A—C14—H14B	109.5	C3—Fe2—C1	68.70 (12)
C13—C14—H14C	109.5	C2—Fe2—C1	41.05 (10)
H14A—C14—H14C	109.5	C11—O1—Fe1	131.01 (19)
H14B—C14—H14C	109.5	C13—O2—Fe1	129.69 (19)
O3—C15—C16	124.0 (3)	C15—O3—Fe1ⁱ	128.48 (19)
O3—C15—C10	115.0 (2)	C17—O4—Fe1ⁱ	128.29 (18)
C16—C15—C10	121.0 (3)	C19—O5—Fe1ⁱ	128.41 (7)
C17—C16—C15	123.1 (3)	C19—O5—Fe1	128.41 (7)
C17—C16—H16	118.4	Fe1ⁱ—O5—Fe1	103.19 (13)
C15—C16—H16	118.4	C19—O5—H20	108.2
O4—C17—C16	125.1 (3)	Fe1ⁱ—O5—H20	40.6
O4—C17—C18	114.5 (3)	Fe1—O5—H20	111.8
C16—C17—C18	120.4 (3)	C20—O6—Fe1	127.74 (6)
C17—C18—H18A	109.5	C20—O6—Fe1ⁱ	127.74 (6)
C17—C18—H18B	109.5	Fe1—O6—Fe1ⁱ	104.52 (13)
H18A—C18—H18B	109.5	C20—O6—H21	108.2
C17—C18—H18C	109.5	Fe1—O6—H21	102.9
H18A—C18—H18C	109.5	Fe1ⁱ—O6—H21	52.7

Symmetry code: (i) −x, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O4ⁱ	0.96	2.49	3.028 (3)	116
C20—H20C···O4	0.96	2.57	3.028 (3)	110
C19—H19B···O2	0.96	2.53	3.121 (3)	120
C3—H3···O4ⁱⁱ	0.98	2.57	3.107 (4)	114
O6—H21···O4	0.82	2.44	2.8377 (19)	111
O6—H21···O3	0.82	2.33	3.103 (3)	158
O5—H20···O1ⁱ	0.82	2.33	3.101 (3)	157
O5—H20···O2ⁱ	0.82	2.32	2.914 (2)	129

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

Experimental details

Crystal data
Chemical formula	[Fe₄(C₉H₈O₂)₄(CH₄O)₂]
M_r	880.10
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	291
a, b, c (Å)	14.599 (3), 19.290 (4), 12.955 (3)
V (Å³)	3648.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.685, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	16837, 4079, 3473
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.069, 1.05
No. of reflections	4079
No. of parameters	242
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28
Absolute structure	Flack (1983), 1899 Friedel pairs
Absolute structure parameter	−0.001 (16)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yan, C.-G., Zhu, M.-J., Sun, J., Liu, W.-L. & Shi, Y.-C. (2007). J. Coord. Chem. 60, 1083–1091. Web of Science CSD CrossRef CAS Google Scholar

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