Tetra­carbonyl-1κ2C,3κ2C-bis[1,3(η5)-cyclo­penta­dien­yl]dihydroxido-2κ2O-diirontin(2 Fe—Sn) monohydrate

Kössel, S.; Wagner, C.; Merzweiler, K.

doi:10.1107/S1600536810021975

metal-organic compounds

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Volume 66| Part 7| July 2010| Page m811

doi:10.1107/S1600536810021975

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Tetracarbonyl-1κ²C,3κ²C-bis[1,3(η⁵)-cyclopentadienyl]dihydroxido-2κ²O-diirontin(2 Fe—Sn) monohydrate

Stefanie Kössel,^a Christoph Wagner ^a and Kurt Merzweiler ^a ^*

^aInstitut für Chemie, Naturwissenschaftliche Fakulät II, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Strasse 2, 06120 Halle, Germany
^*Correspondence e-mail: kurt.merzweiler@chemie.uni-halle.de

(Received 14 May 2010; accepted 8 June 2010; online 18 June 2010)

In the title hydrate, [Fe₂Sn(C₅H₅)₂(OH)₂(CO)₄]·H₂O, the central Sn atom is tetrahedrally coordinated by two {Cp(CO)₂Fe} fragments and two hydroxide groups. The [{Cp(CO)₂Fe}₂Sn(OH)₂] and water molecules are linked by O—H⋯O hydrogen bridges, giving two-dimensional arrays with 4.8² topology that stack along the c axis.

Related literature

For the crystal structures of diorganotin dihydroxides, see: Pu et al. (2001 ); Tajima et al. (2006 ). For the related structure of [{Cp(CO)₂Fe}₂Sn(OH)₂] (without experimental details), see: Nesmeyanov et al. (1966 ). For related structures [{Cp(CO)₂Fe}₃SnOH, see: O'Connor & Corey (1967 ); Fässler & Schütz (1997 ).

Experimental

Crystal data

[Fe₂Sn(C₅H₅)₂(OH)₂(CO)₄]·H₂O
M_r = 524.64
Triclinic, $[P \overline 1]$
a = 7.1760 (6) Å
b = 9.7262 (9) Å
c = 12.063 (1) Å
α = 92.046 (7)°
β = 90.822 (7)°
γ = 97.560 (7)°
V = 833.93 (12) Å³
Z = 2
Mo Kα radiation
μ = 3.24 mm⁻¹
T = 200 K
0.16 × 0.15 × 0.07 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: numerical (X-AREA; Stoe & Cie, 2009 ) T_min = 0.607, T_max = 0.806
7904 measured reflections
3641 independent reflections
3374 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.048
S = 1.05
3641 reflections
233 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O7ⁱ	0.80 (4)	2.01 (4)	2.778 (2)	159 (4)
O6—H2⋯O1ⁱⁱ	0.80 (3)	2.44 (3)	3.212 (2)	160 (3)
O7—H3⋯O5ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.773 (3)	176 (4)
O7—H4⋯O6	0.82 (3)	1.90 (3)	2.709 (2)	174 (4)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021975/tk2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021975/tk2678Isup2.hkl

checkCIF report

Comment top

In the structure of the title compound, (I), a known material but with limited characterisation data (Nesmeyanov et al., 1966), the tin atom is surrounded by two {Cp(CO)₂Fe} fragments and two OH groups in a distorted tetrahedral arrangement (Fig. 1). The {Cp(CO)₂Fe}₂Sn unit shows experimentally equivalent Sn—Fe bond lengths of 2.534 (1) and 2.535 (1) Å, and a Fe—Sn—Fe angle of 122.8 (1) °. Compared to [{Cp(CO)₂Fe}₂SnCl₂] (Sn—Fe: 2.492 (8) Å; Fe—Sn—Fe: 128.6 (3) °), the Sn—Fe distances are around 0.05 Å longer and the Fe—Sn—Fe angle is reduced by 6° (O'Connor & Corey, 1967). Compound (I) also contains two Sn—O bonds of 2.016 (2) and 2.026 (2) Å which are close to the Sn—O distance found in [{Cp(CO)₂Fe}₃SnOH] (Fässler & Schütz, 1997). As compared to the dihydroxy derivatives (2,6-Mes₂H₃C₆)₂Sn(OH)₂ (Sn—O: 1.97 (4) Å ) (Pu et al., 2001) and (Bbt)(Titp)Sn(OH)₂ (Sn—O: 1.990 (4) and 2.005 (4) Å) ((Bbt = 2,6-{(CH(SiMe₃)₂}₂-4-{CSiMe₃}₃H₂C₆; Titp = 2,6-{2,4-(i-Pr)₂H₃C₆}H₄C₆) (Tajima et al., 2006), the Sn—O bonds in (I) are slightly enlongated. This might be due to the presence of hydrogen bonds involving both OH groups but in different types of hydrogen bridges, Fig. 2. Two hydrogen bridges are formed between the O7-water molecule as donator and the hydroxyl oxygen atoms O5ⁱⁱⁱ and O6 as acceptors. Additionally, the hydroxyl group O5–H1 forms a hydrogen bridge to the water oxygen atom O7ⁱ and the hydroxyl group O6–H2 is involved in a hydrogen bridge with the carbonyl oxygen atom O1ⁱⁱ. Consequently, a two-dimensional array is formed that comprises 8-membered O₄H₄ rings (I in Fig. 2), 12-membered Sn₂O₆H₄ rings (II), 12-membered Sn₂Fe₂C₂O₄H₂ rings (III) and 20-membered Sn₂Fe₂C₂O₈H₆ rings (IV). The interconnection of theses rings leads to a three-connected net with 4.8²topology.

Related literature top

For the crystal structures of diorganotin dihydroxides, see: Pu et al. (2001); Tajima et al. (2006). For a short reference to [{Cp(CO)₂Fe}₂Sn(OH)₂] (without experimental details), see: Nesmeyanov et al. (1966). For related structures [{Cp(CO)₂Fe}₃SnOH, see: O'Connor & Corey (1967); Fässler & Schütz (1997).

Experimental top

To a solution of 3.24 g (6.2 mmol) [{Cp(CO)₂Fe}₂SnCl₂] in CH₂Cl₂ (15 ml), a solution of NaOH (2.4 g, 60 mmol) in water (9 ml) was added at 273 K. Within 3 h, yellow-orange crystals of (I) were formed at the CH₂Cl₂/H₂O interface. The precipitate was filtered, washed with water, and dried. Yield: 2.37 g (73 %). Anal. Calcd. for C₁₄H₁₄Fe₂O₇Sn (524.64): C 32.05, H 2.69 %. Found: C 31.33, H 2.61 %. ¹H-NMR (methanol-d₄): d = 5.11 (s, 10 H, Cp) p.p.m. ¹³C-NMR (methanol-d₄): d = 84.3 (Cp), 214.0 (CO) p.p.m. ¹¹⁹Sn-NMR (methanol-d₄): d = 454 (s) p.p.m.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing displacement ellipsoids at the 40 % probability level.
	Fig. 2. Part of the hydrogen bond network of (I) exhibiting 4.8² topology (Cp groups and CO groups not involved in hydrogen bonding are omitted for clarity).

Tetracarbonyl-1κ²C,3κ²C-bis[1,3(η⁵)- cyclopentadienyl]dihydroxido-2κ²O-diirontin(2 Fe—Sn) monohydrate top

Crystal data top

[Fe₂Sn(C₅H₅)₂(OH)₂(CO)₄]·H₂O	Z = 2
M_r = 524.64	F(000) = 512
Triclinic, P1	D_x = 2.089 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1760 (6) Å	Cell parameters from 8934 reflections
b = 9.7262 (9) Å	θ = 5.3–53.6°
c = 12.063 (1) Å	µ = 3.24 mm⁻¹
α = 92.046 (7)°	T = 200 K
β = 90.822 (7)°	Prism, orange
γ = 97.560 (7)°	0.16 × 0.15 × 0.07 mm
V = 833.93 (12) Å³

Data collection top

Stoe IPDS 2T diffractometer	3641 independent reflections
Radiation source: fine-focus sealed tube	3374 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.0°, θ_min = 2.7°
rotation method scans	h = −9→9
Absorption correction: numerical (X-AREA; Stoe & Cie, 2009)	k = −12→11
T_min = 0.607, T_max = 0.806	l = −15→15
7904 measured reflections

Refinement top

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0325P)² + 0.1254P] where P = (F_o² + 2F_c²)/3
3641 reflections	(Δ/σ)_max = 0.002
233 parameters	Δρ_max = 0.44 e Å⁻³
4 restraints	Δρ_min = −0.62 e Å⁻³
0 constraints

Crystal data top

[Fe₂Sn(C₅H₅)₂(OH)₂(CO)₄]·H₂O	γ = 97.560 (7)°
M_r = 524.64	V = 833.93 (12) Å³
Triclinic, P1	Z = 2
a = 7.1760 (6) Å	Mo Kα radiation
b = 9.7262 (9) Å	µ = 3.24 mm⁻¹
c = 12.063 (1) Å	T = 200 K
α = 92.046 (7)°	0.16 × 0.15 × 0.07 mm
β = 90.822 (7)°

Data collection top

Stoe IPDS 2T diffractometer	3641 independent reflections
Absorption correction: numerical (X-AREA; Stoe & Cie, 2009)	3374 reflections with I > 2σ(I)
T_min = 0.607, T_max = 0.806	R_int = 0.018
7904 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	4 restraints
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.44 e Å⁻³
3641 reflections	Δρ_min = −0.62 e Å⁻³
233 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.7075 (3)	1.0222 (2)	0.84442 (18)	0.0283 (4)
C2	0.7280 (4)	0.9336 (2)	0.64429 (19)	0.0350 (5)
C3	1.1193 (3)	0.9698 (3)	0.8631 (2)	0.0393 (5)
H3A	1.1195	0.9477	0.9384	0.047*
C4	1.1382 (3)	0.8774 (3)	0.7722 (2)	0.0367 (5)
H4A	1.1547	0.7834	0.7761	0.044*
C5	1.1278 (3)	0.9515 (3)	0.6750 (2)	0.0395 (5)
H5A	1.1349	0.9151	0.6022	0.047*
C6	1.1047 (3)	1.0908 (3)	0.7051 (2)	0.0418 (6)
H6A	1.0946	1.1626	0.6561	0.050*
C7	1.0999 (3)	1.1017 (3)	0.8212 (2)	0.0418 (6)
H7A	1.0861	1.1824	0.8638	0.050*
C8	0.4498 (3)	0.5867 (2)	0.65282 (18)	0.0318 (5)
C9	0.7911 (3)	0.6018 (2)	0.58481 (18)	0.0298 (4)
C10	0.6902 (6)	0.3898 (3)	0.8208 (2)	0.0596 (10)
H10A	0.7103	0.4226	0.8948	0.072*
C11	0.5143 (4)	0.3457 (3)	0.7690 (2)	0.0482 (7)
H11A	0.3964	0.3455	0.8019	0.058*
C12	0.5462 (3)	0.3020 (2)	0.6590 (2)	0.0356 (5)
H12A	0.4534	0.2666	0.6059	0.043*
C13	0.7395 (4)	0.3204 (2)	0.6431 (2)	0.0378 (5)
H13A	0.7997	0.2992	0.5771	0.045*
C14	0.8301 (4)	0.3761 (3)	0.7426 (3)	0.0509 (8)
H14A	0.9604	0.3997	0.7543	0.061*
O1	0.5976 (3)	1.06847 (19)	0.89760 (16)	0.0420 (4)
O2	0.6339 (3)	0.9215 (2)	0.56601 (17)	0.0582 (6)
O3	0.3141 (3)	0.6314 (2)	0.63030 (16)	0.0492 (5)
O4	0.8793 (3)	0.6577 (2)	0.51681 (15)	0.0450 (4)
O5	0.9048 (2)	0.67485 (17)	0.94997 (13)	0.0328 (3)
H1	0.851 (5)	0.625 (4)	0.994 (3)	0.080 (13)*
O6	0.5023 (2)	0.71819 (18)	0.90976 (14)	0.0353 (4)
H2	0.502 (4)	0.783 (3)	0.953 (2)	0.049 (9)*
O7	0.1945 (2)	0.5242 (2)	0.89430 (15)	0.0376 (4)
H4	0.292 (3)	0.578 (3)	0.901 (3)	0.057 (10)*
H3	0.112 (5)	0.572 (4)	0.910 (4)	0.090 (15)*
Sn1	0.740305 (17)	0.716117 (13)	0.821699 (10)	0.02046 (5)
Fe1	0.87665 (4)	0.95526 (3)	0.76220 (2)	0.02269 (7)
Fe2	0.65366 (4)	0.51278 (3)	0.68520 (2)	0.02259 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0331 (11)	0.0212 (9)	0.0303 (10)	0.0017 (8)	0.0000 (8)	0.0036 (8)
C2	0.0458 (13)	0.0272 (11)	0.0330 (12)	0.0079 (10)	−0.0006 (10)	0.0060 (9)
C3	0.0238 (10)	0.0580 (16)	0.0360 (12)	0.0042 (10)	−0.0036 (9)	0.0052 (11)
C4	0.0243 (10)	0.0338 (12)	0.0533 (14)	0.0064 (9)	0.0080 (9)	0.0078 (10)
C5	0.0337 (12)	0.0454 (14)	0.0392 (13)	0.0034 (10)	0.0146 (10)	0.0015 (10)
C6	0.0324 (12)	0.0335 (12)	0.0581 (16)	−0.0056 (10)	0.0098 (11)	0.0155 (11)
C7	0.0286 (11)	0.0352 (13)	0.0580 (16)	−0.0055 (10)	0.0021 (10)	−0.0119 (11)
C8	0.0340 (11)	0.0346 (12)	0.0260 (10)	0.0036 (9)	−0.0002 (8)	−0.0065 (8)
C9	0.0341 (11)	0.0287 (11)	0.0274 (10)	0.0079 (9)	0.0007 (8)	−0.0018 (8)
C10	0.124 (3)	0.0198 (11)	0.0302 (12)	−0.0077 (14)	−0.0171 (15)	0.0043 (9)
C11	0.0671 (18)	0.0231 (11)	0.0522 (15)	−0.0056 (11)	0.0291 (14)	0.0042 (10)
C12	0.0409 (12)	0.0214 (10)	0.0424 (13)	−0.0020 (9)	−0.0056 (10)	−0.0036 (9)
C13	0.0450 (13)	0.0246 (11)	0.0454 (13)	0.0110 (10)	0.0065 (10)	0.0010 (9)
C14	0.0486 (15)	0.0267 (12)	0.077 (2)	0.0026 (11)	−0.0287 (15)	0.0095 (12)
O1	0.0448 (10)	0.0374 (9)	0.0466 (10)	0.0143 (8)	0.0139 (8)	0.0006 (8)
O2	0.0768 (15)	0.0588 (13)	0.0399 (11)	0.0149 (11)	−0.0259 (10)	0.0021 (9)
O3	0.0404 (10)	0.0665 (13)	0.0441 (10)	0.0240 (9)	−0.0098 (8)	−0.0100 (9)
O4	0.0508 (11)	0.0462 (10)	0.0377 (9)	0.0021 (8)	0.0165 (8)	0.0090 (8)
O5	0.0357 (8)	0.0326 (8)	0.0294 (8)	0.0022 (7)	−0.0083 (6)	0.0059 (6)
O6	0.0304 (8)	0.0329 (9)	0.0414 (9)	0.0003 (7)	0.0125 (7)	−0.0051 (7)
O7	0.0282 (8)	0.0444 (10)	0.0398 (9)	0.0015 (8)	0.0035 (7)	0.0093 (8)
Sn1	0.02214 (7)	0.01840 (7)	0.02058 (7)	0.00165 (5)	0.00004 (5)	0.00084 (5)
Fe1	0.02485 (14)	0.01989 (14)	0.02322 (14)	0.00213 (11)	0.00141 (11)	0.00217 (10)
Fe2	0.02546 (14)	0.02059 (14)	0.02121 (14)	0.00140 (11)	0.00051 (10)	−0.00018 (10)

Geometric parameters (Å, º) top

C1—O1	1.151 (3)	C10—C14	1.404 (5)
C1—Fe1	1.754 (2)	C10—C11	1.408 (5)
C2—O2	1.147 (3)	C10—Fe2	2.094 (3)
C2—Fe1	1.755 (2)	C10—H10A	0.9500
C3—C4	1.412 (4)	C11—C12	1.409 (4)
C3—C7	1.419 (4)	C11—Fe2	2.093 (2)
C3—Fe1	2.097 (2)	C11—H11A	0.9500
C3—H3A	0.9500	C12—C13	1.393 (3)
C4—C5	1.405 (4)	C12—Fe2	2.105 (2)
C4—Fe1	2.118 (2)	C12—H12A	0.9500
C4—H4A	0.9500	C13—C14	1.413 (4)
C5—C6	1.422 (4)	C13—Fe2	2.094 (2)
C5—Fe1	2.103 (2)	C13—H13A	0.9500
C5—H5A	0.9500	C14—Fe2	2.082 (3)
C6—C7	1.401 (4)	C14—H14A	0.9500
C6—Fe1	2.103 (2)	O5—Sn1	2.0164 (15)
C6—H6A	0.9500	O5—H1	0.80 (4)
C7—Fe1	2.097 (2)	O6—Sn1	2.0264 (15)
C7—H7A	0.9500	O6—H2	0.80 (3)
C8—O3	1.150 (3)	O7—H4	0.82 (4)
C8—Fe2	1.758 (2)	O7—H3	0.82 (3)
C9—O4	1.151 (3)	Sn1—Fe1	2.5344 (4)
C9—Fe2	1.753 (2)	Sn1—Fe2	2.5345 (4)

O1—C1—Fe1	178.8 (2)	Sn1—O6—H2	116 (2)
O2—C2—Fe1	178.4 (2)	H4—O7—H3	104 (4)
C4—C3—C7	108.1 (2)	O5—Sn1—O6	96.19 (7)
C4—C3—Fe1	71.22 (14)	O5—Sn1—Fe1	105.28 (5)
C7—C3—Fe1	70.21 (14)	O6—Sn1—Fe1	112.76 (5)
C4—C3—H3A	125.9	O5—Sn1—Fe2	114.09 (5)
C7—C3—H3A	125.9	O6—Sn1—Fe2	102.65 (5)
Fe1—C3—H3A	124.2	Fe1—Sn1—Fe2	122.793 (12)
C5—C4—C3	107.6 (2)	C1—Fe1—C2	93.08 (11)
C5—C4—Fe1	70.02 (14)	C1—Fe1—C7	94.64 (10)
C3—C4—Fe1	69.62 (13)	C2—Fe1—C7	136.18 (11)
C5—C4—H4A	126.2	C1—Fe1—C3	105.40 (10)
C3—C4—H4A	126.2	C2—Fe1—C3	161.02 (11)
Fe1—C4—H4A	125.7	C7—Fe1—C3	39.57 (11)
C4—C5—C6	108.6 (2)	C1—Fe1—C6	119.32 (10)
C4—C5—Fe1	71.11 (13)	C2—Fe1—C6	101.41 (11)
C6—C5—Fe1	70.21 (13)	C7—Fe1—C6	38.99 (11)
C4—C5—H5A	125.7	C3—Fe1—C6	65.91 (11)
C6—C5—H5A	125.7	C1—Fe1—C5	158.47 (10)
Fe1—C5—H5A	124.6	C2—Fe1—C5	95.64 (11)
C7—C6—C5	107.6 (2)	C7—Fe1—C5	65.68 (10)
C7—C6—Fe1	70.27 (13)	C3—Fe1—C5	65.51 (10)
C5—C6—Fe1	70.28 (13)	C6—Fe1—C5	39.51 (10)
C7—C6—H6A	126.2	C1—Fe1—C4	142.15 (10)
C5—C6—H6A	126.2	C2—Fe1—C4	123.75 (11)
Fe1—C6—H6A	124.8	C7—Fe1—C4	65.92 (10)
C6—C7—C3	108.1 (2)	C3—Fe1—C4	39.16 (10)
C6—C7—Fe1	70.73 (14)	C6—Fe1—C4	65.89 (10)
C3—C7—Fe1	70.22 (13)	C5—Fe1—C4	38.87 (10)
C6—C7—H7A	125.9	C1—Fe1—Sn1	87.56 (7)
C3—C7—H7A	125.9	C2—Fe1—Sn1	89.50 (8)
Fe1—C7—H7A	124.7	C7—Fe1—Sn1	133.84 (8)
O3—C8—Fe2	178.0 (2)	C3—Fe1—Sn1	95.50 (8)
O4—C9—Fe2	178.2 (2)	C6—Fe1—Sn1	149.88 (8)
C14—C10—C11	108.0 (2)	C5—Fe1—Sn1	112.11 (8)
C14—C10—Fe2	69.88 (15)	C4—Fe1—Sn1	84.64 (7)
C11—C10—Fe2	70.31 (16)	C9—Fe2—C8	94.65 (11)
C14—C10—H10A	126.0	C9—Fe2—C14	102.33 (12)
C11—C10—H10A	126.0	C8—Fe2—C14	161.44 (12)
Fe2—C10—H10A	125.4	C9—Fe2—C11	159.00 (10)
C10—C11—C12	108.0 (3)	C8—Fe2—C11	95.48 (12)
C10—C11—Fe2	70.39 (14)	C14—Fe2—C11	66.05 (12)
C12—C11—Fe2	70.83 (13)	C9—Fe2—C13	94.25 (10)
C10—C11—H11A	126.0	C8—Fe2—C13	132.50 (10)
C12—C11—H11A	126.0	C14—Fe2—C13	39.55 (11)
Fe2—C11—H11A	124.4	C11—Fe2—C13	65.48 (10)
C13—C12—C11	107.8 (2)	C9—Fe2—C10	138.61 (14)
C13—C12—Fe2	70.21 (13)	C8—Fe2—C10	125.93 (14)
C11—C12—Fe2	69.93 (13)	C14—Fe2—C10	39.28 (14)
C13—C12—H12A	126.1	C11—Fe2—C10	39.30 (13)
C11—C12—H12A	126.1	C13—Fe2—C10	65.69 (11)
Fe2—C12—H12A	125.4	C9—Fe2—C12	120.77 (10)
C12—C13—C14	108.6 (2)	C8—Fe2—C12	98.94 (10)
C12—C13—Fe2	71.05 (13)	C14—Fe2—C12	65.94 (10)
C14—C13—Fe2	69.75 (15)	C11—Fe2—C12	39.23 (10)
C12—C13—H13A	125.7	C13—Fe2—C12	38.74 (10)
C14—C13—H13A	125.7	C10—Fe2—C12	65.76 (10)
Fe2—C13—H13A	125.1	C9—Fe2—Sn1	89.66 (7)
C10—C14—C13	107.5 (2)	C8—Fe2—Sn1	87.25 (7)
C10—C14—Fe2	70.84 (17)	C14—Fe2—Sn1	100.14 (8)
C13—C14—Fe2	70.70 (14)	C11—Fe2—Sn1	109.15 (8)
C10—C14—H14A	126.2	C13—Fe2—Sn1	139.34 (8)
C13—C14—H14A	126.2	C10—Fe2—Sn1	85.09 (7)
Fe2—C14—H14A	123.9	C12—Fe2—Sn1	147.97 (7)
Sn1—O5—H1	114 (3)

C7—C3—C4—C5	−0.8 (3)	Fe2—Sn1—Fe1—C2	37.77 (8)
Fe1—C3—C4—C5	60.01 (17)	O5—Sn1—Fe1—C7	−2.24 (11)
C7—C3—C4—Fe1	−60.82 (16)	O6—Sn1—Fe1—C7	101.40 (11)
C3—C4—C5—C6	0.7 (3)	Fe2—Sn1—Fe1—C7	−135.05 (10)
Fe1—C4—C5—C6	60.48 (17)	O5—Sn1—Fe1—C3	8.91 (9)
C3—C4—C5—Fe1	−59.76 (16)	O6—Sn1—Fe1—C3	112.55 (9)
C4—C5—C6—C7	−0.3 (3)	Fe2—Sn1—Fe1—C3	−123.89 (7)
Fe1—C5—C6—C7	60.69 (17)	O5—Sn1—Fe1—C6	58.28 (17)
C4—C5—C6—Fe1	−61.04 (17)	O6—Sn1—Fe1—C6	161.92 (17)
C5—C6—C7—C3	−0.2 (3)	Fe2—Sn1—Fe1—C6	−74.52 (16)
Fe1—C6—C7—C3	60.54 (16)	O5—Sn1—Fe1—C5	74.68 (10)
C5—C6—C7—Fe1	−60.69 (17)	O6—Sn1—Fe1—C5	178.33 (10)
C4—C3—C7—C6	0.6 (3)	Fe2—Sn1—Fe1—C5	−58.12 (8)
Fe1—C3—C7—C6	−60.86 (17)	O5—Sn1—Fe1—C4	46.59 (9)
C4—C3—C7—Fe1	61.46 (16)	O6—Sn1—Fe1—C4	150.23 (9)
C14—C10—C11—C12	1.2 (3)	Fe2—Sn1—Fe1—C4	−86.21 (7)
Fe2—C10—C11—C12	61.16 (18)	C10—C14—Fe2—C9	161.03 (16)
C14—C10—C11—Fe2	−59.95 (18)	C13—C14—Fe2—C9	−81.63 (17)
C10—C11—C12—C13	−0.6 (3)	C10—C14—Fe2—C8	−43.2 (4)
Fe2—C11—C12—C13	60.25 (17)	C13—C14—Fe2—C8	74.2 (4)
C10—C11—C12—Fe2	−60.88 (17)	C10—C14—Fe2—C11	−37.42 (16)
C11—C12—C13—C14	−0.2 (3)	C13—C14—Fe2—C11	79.92 (17)
Fe2—C12—C13—C14	59.89 (17)	C10—C14—Fe2—C13	−117.3 (2)
C11—C12—C13—Fe2	−60.08 (17)	C13—C14—Fe2—C10	117.3 (2)
C11—C10—C14—C13	−1.3 (3)	C10—C14—Fe2—C12	−80.55 (17)
Fe2—C10—C14—C13	−61.54 (17)	C13—C14—Fe2—C12	36.79 (15)
C11—C10—C14—Fe2	60.22 (19)	C10—C14—Fe2—Sn1	69.15 (15)
C12—C13—C14—C10	0.9 (3)	C13—C14—Fe2—Sn1	−173.52 (14)
Fe2—C13—C14—C10	61.63 (18)	C10—C11—Fe2—C9	97.1 (4)
C12—C13—C14—Fe2	−60.70 (17)	C12—C11—Fe2—C9	−21.1 (4)
C6—C7—Fe1—C1	−132.89 (16)	C10—C11—Fe2—C8	−144.44 (19)
C3—C7—Fe1—C1	108.66 (15)	C12—C11—Fe2—C8	97.44 (17)
C6—C7—Fe1—C2	−33.6 (2)	C10—C11—Fe2—C14	37.40 (18)
C3—C7—Fe1—C2	−152.00 (17)	C12—C11—Fe2—C14	−80.73 (18)
C6—C7—Fe1—C3	118.4 (2)	C10—C11—Fe2—C13	81.0 (2)
C3—C7—Fe1—C6	−118.4 (2)	C12—C11—Fe2—C13	−37.17 (16)
C6—C7—Fe1—C5	38.06 (16)	C12—C11—Fe2—C10	−118.1 (3)
C3—C7—Fe1—C5	−80.38 (16)	C10—C11—Fe2—C12	118.1 (3)
C6—C7—Fe1—C4	80.86 (17)	C10—C11—Fe2—Sn1	−55.45 (19)
C3—C7—Fe1—C4	−37.59 (15)	C12—C11—Fe2—Sn1	−173.58 (14)
C6—C7—Fe1—Sn1	136.03 (14)	C12—C13—Fe2—C9	−136.65 (16)
C3—C7—Fe1—Sn1	17.59 (19)	C14—C13—Fe2—C9	104.26 (18)
C4—C3—Fe1—C1	163.50 (15)	C12—C13—Fe2—C8	−36.4 (2)
C7—C3—Fe1—C1	−78.37 (16)	C14—C13—Fe2—C8	−155.46 (18)
C4—C3—Fe1—C2	−30.2 (4)	C12—C13—Fe2—C14	119.1 (2)
C7—C3—Fe1—C2	88.0 (4)	C12—C13—Fe2—C11	37.63 (16)
C4—C3—Fe1—C7	−118.1 (2)	C14—C13—Fe2—C11	−81.46 (19)
C4—C3—Fe1—C6	−80.82 (16)	C12—C13—Fe2—C10	80.98 (18)
C7—C3—Fe1—C6	37.30 (15)	C14—C13—Fe2—C10	−38.11 (18)
C4—C3—Fe1—C5	−37.30 (15)	C14—C13—Fe2—C12	−119.1 (2)
C7—C3—Fe1—C5	80.83 (16)	C12—C13—Fe2—Sn1	128.91 (14)
C7—C3—Fe1—C4	118.1 (2)	C14—C13—Fe2—Sn1	9.8 (2)
C4—C3—Fe1—Sn1	74.52 (14)	C14—C10—Fe2—C9	−28.7 (2)
C7—C3—Fe1—Sn1	−167.35 (14)	C11—C10—Fe2—C9	−147.46 (18)
C7—C6—Fe1—C1	56.88 (19)	C14—C10—Fe2—C8	164.40 (15)
C5—C6—Fe1—C1	174.86 (16)	C11—C10—Fe2—C8	45.6 (2)
C7—C6—Fe1—C2	157.02 (16)	C11—C10—Fe2—C14	−118.8 (2)
C5—C6—Fe1—C2	−85.00 (17)	C14—C10—Fe2—C11	118.8 (2)
C5—C6—Fe1—C7	118.0 (2)	C14—C10—Fe2—C13	38.37 (15)
C7—C6—Fe1—C3	−37.85 (16)	C11—C10—Fe2—C13	−80.39 (17)
C5—C6—Fe1—C3	80.13 (17)	C14—C10—Fe2—C12	81.04 (16)
C7—C6—Fe1—C5	−118.0 (2)	C11—C10—Fe2—C12	−37.72 (15)
C7—C6—Fe1—C4	−80.93 (17)	C14—C10—Fe2—Sn1	−112.59 (15)
C5—C6—Fe1—C4	37.05 (16)	C11—C10—Fe2—Sn1	128.65 (17)
C7—C6—Fe1—Sn1	−93.7 (2)	C13—C12—Fe2—C9	52.82 (19)
C5—C6—Fe1—Sn1	24.3 (3)	C11—C12—Fe2—C9	171.38 (18)
C4—C5—Fe1—C1	106.5 (3)	C13—C12—Fe2—C8	153.73 (16)
C6—C5—Fe1—C1	−12.3 (4)	C11—C12—Fe2—C8	−87.71 (19)
C4—C5—Fe1—C2	−140.10 (16)	C13—C12—Fe2—C14	−37.55 (17)
C6—C5—Fe1—C2	101.11 (17)	C11—C12—Fe2—C14	81.0 (2)
C4—C5—Fe1—C7	81.22 (17)	C13—C12—Fe2—C11	−118.6 (2)
C6—C5—Fe1—C7	−37.57 (17)	C11—C12—Fe2—C13	118.6 (2)
C4—C5—Fe1—C3	37.57 (16)	C13—C12—Fe2—C10	−80.77 (19)
C6—C5—Fe1—C3	−81.22 (18)	C11—C12—Fe2—C10	37.8 (2)
C4—C5—Fe1—C6	118.8 (2)	C13—C12—Fe2—Sn1	−107.06 (17)
C6—C5—Fe1—C4	−118.8 (2)	C11—C12—Fe2—Sn1	11.5 (2)
C4—C5—Fe1—Sn1	−48.34 (16)	O5—Sn1—Fe2—C9	−112.12 (9)
C6—C5—Fe1—Sn1	−167.13 (14)	O6—Sn1—Fe2—C9	145.09 (9)
C5—C4—Fe1—C1	−145.01 (17)	Fe1—Sn1—Fe2—C9	17.05 (8)
C3—C4—Fe1—C1	−26.5 (2)	O5—Sn1—Fe2—C8	153.20 (9)
C5—C4—Fe1—C2	50.15 (19)	O6—Sn1—Fe2—C8	50.41 (9)
C3—C4—Fe1—C2	168.67 (16)	Fe1—Sn1—Fe2—C8	−77.63 (8)
C5—C4—Fe1—C7	−80.53 (17)	O5—Sn1—Fe2—C14	−9.65 (11)
C3—C4—Fe1—C7	37.98 (16)	O6—Sn1—Fe2—C14	−112.44 (11)
C5—C4—Fe1—C3	−118.5 (2)	Fe1—Sn1—Fe2—C14	119.52 (9)
C5—C4—Fe1—C6	−37.65 (16)	O5—Sn1—Fe2—C11	58.36 (11)
C3—C4—Fe1—C6	80.87 (17)	O6—Sn1—Fe2—C11	−44.43 (11)
C3—C4—Fe1—C5	118.5 (2)	Fe1—Sn1—Fe2—C11	−172.47 (10)
C5—C4—Fe1—Sn1	135.96 (15)	O5—Sn1—Fe2—C13	−15.99 (12)
C3—C4—Fe1—Sn1	−105.53 (14)	O6—Sn1—Fe2—C13	−118.78 (12)
O5—Sn1—Fe1—C1	−96.33 (9)	Fe1—Sn1—Fe2—C13	113.18 (11)
O6—Sn1—Fe1—C1	7.31 (9)	O5—Sn1—Fe2—C10	26.78 (13)
Fe2—Sn1—Fe1—C1	130.86 (7)	O6—Sn1—Fe2—C10	−76.01 (13)
O5—Sn1—Fe1—C2	170.57 (9)	Fe1—Sn1—Fe2—C10	155.95 (12)
O6—Sn1—Fe1—C2	−85.79 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O7ⁱ	0.80 (4)	2.01 (4)	2.778 (2)	159 (4)
O6—H2···O1ⁱⁱ	0.80 (3)	2.44 (3)	3.212 (2)	160 (3)
O7—H3···O5ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.773 (3)	176 (4)
O7—H4···O6	0.82 (3)	1.90 (3)	2.709 (2)	174 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe₂Sn(C₅H₅)₂(OH)₂(CO)₄]·H₂O
M_r	524.64
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	7.1760 (6), 9.7262 (9), 12.063 (1)
α, β, γ (°)	92.046 (7), 90.822 (7), 97.560 (7)
V (Å³)	833.93 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.16 × 0.15 × 0.07

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	Numerical (X-AREA; Stoe & Cie, 2009)
T_min, T_max	0.607, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	7904, 3641, 3374
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.048, 1.05
No. of reflections	3641
No. of parameters	233
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.62

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O7ⁱ	0.80 (4)	2.01 (4)	2.778 (2)	159 (4)
O6—H2···O1ⁱⁱ	0.80 (3)	2.44 (3)	3.212 (2)	160 (3)
O7—H3···O5ⁱⁱⁱ	0.82 (4)	1.96 (4)	2.773 (3)	176 (4)
O7—H4···O6	0.82 (3)	1.90 (3)	2.709 (2)	174 (4)

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

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Fässler, T. F. & Schütz, U. (1997). J. Organomet. Chem. 541, 269–276. CSD CrossRef CAS Web of Science Google Scholar
Nesmeyanov, A. N., Anisimov, K. N., Kolobova, N. E. & Skirpkin, V. V. (1966). Izv. Akad. Nauk Ser. Khim. 7, 1292–1292. Google Scholar
O'Connor, J. E. & Corey, E. R. (1967). Inorg. Chem. 6, 968–971. CSD CrossRef CAS Web of Science Google Scholar
Pu, L., Hardman, N. J. & Power, P. P. (2001). Organometallics, 20, 5105–5109. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2009). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Tajima, T., Takeda, N., Sasamori, T. & Tokitoh, N. (2006). Organometallics, 25, 3552–3553. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 7| July 2010| Page m811

doi:10.1107/S1600536810021975

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