Carbon-yl(η-cyclo-penta-dien-yl)(pyridine)(triethyl-stann-yl)iron(II).

In the title complex, [Fe(C(5)H(5)){Sn(C(2)H(5))(3)}(C(5)H(5)N)(CO)], the Fe atom is coordinated by carbonyl, pyridine, triethyl-stannyl and cyclo-penta-dienyl ligands in a typical three-legged piano-stool configuration. The Fe-Sn and Fe-N bond distances are 2.5455 (13) and 1.984 (6) Å, respectively.

Related literature

For background, see: Nakazawa et al. (2007 ▶). Applications of transition metal complexes with a stannyl ligand are reviewed by Smith et al. (2000 ▶). For a related transition metal stannyl complex having a pyridine ligand, see: Rickard et al. (1999 ▶). For structures of related silyl analogues, see: Iwata et al. (2003 ▶); Nakazawa et al. (2007 ▶); Itazaki et al. (2007 ▶).

Experimental

Crystal data

[FeSn(C2H5)3(C5H5)(C5H5N)(CO)]

M = 433.92

Monoclinic,

a = 15.038 (4) Å

b = 7.8271 (19) Å

c = 15.717 (4) Å

β = 96.783 (5)°

V = 1837.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.15 mm−1

T = 200 (2) K

0.13 × 0.13 × 0.02 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.768, T max = 0.958

17586 measured reflections

4174 independent reflections

3439 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.138

S = 1.07

4174 reflections

193 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, FePySnR3. DOI: 10.1107/S1600536808037781/wm2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037781/wm2203Isup2.hkl

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

[FeSn(C2H5)3(C5H5)(C5H5N)(CO)]	F000 = 872
Mr = 433.92	Dx = 1.569 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 4766 reflections
a = 15.038 (4) Å	θ = 4.1–27.5º
b = 7.8271 (19) Å	µ = 2.15 mm−1
c = 15.717 (4) Å	T = 200 (2) K
β = 96.783 (5)º	Platelet, red
V = 1837.1 (8) Å3	0.13 × 0.13 × 0.02 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	3439 reflections with I > 2σ(I)
Detector resolution: 14.6199 pixels mm-1	Rint = 0.069
ω scans	θmax = 27.5º
Absorption correction: multi-scan(Jacobson, 1998)	θmin = 4.1º
Tmin = 0.768, Tmax = 0.958	h = −19→18
17586 measured reflections	k = −10→8
4174 independent reflections	l = −20→19

Refinement on F2	3 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.088	w = 1/[σ2(Fo2) + 25.1156P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.54 e Å−3
4174 reflections	Δρmin = −0.49 e Å−3
193 parameters	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Fe1	0.17373 (7)	0.08483 (15)	0.47425 (7)	0.0262 (3)
C1	0.2299 (11)	−0.1470 (15)	0.5222 (7)	0.078 (4)
H1A	0.2698	−0.2160	0.4944	0.093*
C2	0.1358 (12)	−0.1582 (16)	0.5128 (7)	0.086 (4)
H2A	0.1004	−0.2352	0.4764	0.103*
C3	0.1044 (7)	−0.0394 (19)	0.5652 (7)	0.070 (3)
H3A	0.0433	−0.0214	0.5725	0.084*
C4	0.1768 (8)	0.0509 (14)	0.6059 (6)	0.052 (3)
H4A	0.1738	0.1426	0.6451	0.062*
C5	0.2532 (7)	−0.0163 (15)	0.5796 (6)	0.054 (3)
H5A	0.3125	0.0210	0.5978	0.065*
N1	0.1412 (4)	0.0387 (8)	0.3504 (4)	0.0274 (14)
C6	0.1798 (6)	−0.0873 (12)	0.3099 (5)	0.040 (2)
H6A	0.2255	−0.1524	0.3419	0.048*
C7	0.1574 (7)	−0.1279 (13)	0.2252 (6)	0.049 (2)
H7A	0.1872	−0.2181	0.1996	0.059*
C8	0.0916 (7)	−0.0367 (13)	0.1782 (5)	0.045 (2)
H8A	0.0745	−0.0626	0.1195	0.054*
C9	0.0508 (6)	0.0922 (13)	0.2171 (5)	0.042 (2)
H9A	0.0048	0.1577	0.1858	0.050*
C10	0.0771 (6)	0.1266 (11)	0.3024 (5)	0.0334 (19)
H10A	0.0483	0.2173	0.3285	0.040*
C11	0.1287 (6)	0.2880 (12)	0.4731 (5)	0.035 (2)
O1	0.0971 (5)	0.4230 (9)	0.4738 (4)	0.0531 (18)
Sn1	0.31362 (4)	0.23728 (8)	0.43713 (3)	0.03269 (17)
C12	0.3938 (8)	0.3606 (18)	0.5443 (7)	0.072 (4)
H12A	0.4362	0.2750	0.5719	0.086*
H12B	0.4297	0.4514	0.5209	0.086*
C13	0.3452 (9)	0.4377 (17)	0.6116 (8)	0.083 (4)
H13A	0.2973	0.5118	0.5848	0.107*
H13B	0.3870	0.5054	0.6506	0.107*
H13C	0.3193	0.3470	0.6438	0.107*
C14	0.4046 (8)	0.0648 (16)	0.3820 (8)	0.071 (3)
H14A	0.4156	−0.0345	0.4208	0.086*
H14B	0.3739	0.0217	0.3270	0.086*
C15	0.4914 (9)	0.134 (2)	0.3659 (11)	0.108 (5)
H15A	0.4826	0.2192	0.3202	0.141*
H15B	0.5291	0.0410	0.3485	0.141*
H15C	0.5206	0.1871	0.4183	0.141*
C16	0.2821 (7)	0.4348 (14)	0.3418 (7)	0.061 (3)
H16A	0.2572	0.3782	0.2878	0.073*
H16B	0.2338	0.5063	0.3608	0.073*
C17	0.3541 (8)	0.5497 (17)	0.3217 (8)	0.081 (4)
H17A	0.3804	0.6069	0.3742	0.105*
H17B	0.3295	0.6355	0.2800	0.105*
H17C	0.4004	0.4833	0.2975	0.105*

	U11	U22	U33	U12	U13	U23
Fe1	0.0280 (6)	0.0289 (6)	0.0216 (5)	−0.0011 (5)	0.0021 (4)	0.0025 (5)
C1	0.136 (9)	0.048 (7)	0.053 (7)	0.046 (7)	0.027 (7)	0.031 (6)
C2	0.150 (10)	0.053 (7)	0.044 (6)	−0.052 (8)	−0.029 (7)	0.025 (5)
C3	0.039 (5)	0.113 (10)	0.055 (6)	−0.010 (6)	0.000 (5)	0.053 (6)
C4	0.075 (8)	0.053 (6)	0.030 (5)	0.013 (6)	0.012 (5)	0.014 (4)
C5	0.038 (5)	0.075 (8)	0.046 (6)	−0.001 (5)	−0.006 (4)	0.034 (6)
N1	0.029 (3)	0.026 (4)	0.028 (3)	0.000 (3)	0.009 (3)	0.000 (3)
C6	0.043 (5)	0.040 (5)	0.037 (4)	0.007 (4)	0.002 (4)	−0.009 (4)
C7	0.058 (6)	0.048 (6)	0.043 (5)	−0.004 (5)	0.006 (5)	−0.018 (4)
C8	0.057 (6)	0.051 (6)	0.027 (4)	−0.017 (5)	0.007 (4)	−0.007 (4)
C9	0.044 (5)	0.051 (6)	0.028 (4)	−0.002 (5)	−0.004 (4)	0.000 (4)
C10	0.037 (5)	0.033 (5)	0.029 (4)	0.004 (4)	0.002 (3)	0.002 (3)
C11	0.035 (4)	0.046 (6)	0.023 (4)	0.004 (4)	−0.001 (3)	−0.004 (4)
O1	0.066 (5)	0.039 (4)	0.052 (4)	0.020 (4)	−0.001 (3)	−0.010 (3)
Sn1	0.0279 (3)	0.0395 (3)	0.0304 (3)	−0.0058 (3)	0.00236 (19)	0.0041 (3)
C12	0.061 (7)	0.095 (10)	0.056 (7)	−0.042 (7)	−0.004 (5)	−0.002 (7)
C13	0.107 (11)	0.073 (9)	0.067 (8)	−0.018 (8)	0.003 (7)	−0.019 (7)
C14	0.060 (7)	0.066 (8)	0.094 (9)	0.004 (6)	0.031 (6)	0.000 (7)
C15	0.066 (9)	0.121 (14)	0.148 (14)	0.026 (9)	0.051 (9)	0.016 (11)
C16	0.059 (7)	0.052 (7)	0.069 (7)	−0.015 (6)	0.000 (5)	0.029 (6)
C17	0.068 (8)	0.081 (9)	0.095 (9)	0.000 (7)	0.019 (7)	0.046 (8)

Fe1—C11	1.728 (9)	C9—C10	1.379 (11)
Fe1—N1	1.984 (6)	C9—H9A	0.9500
Fe1—C5	2.080 (8)	C10—H10A	0.9500
Fe1—C4	2.082 (9)	C11—O1	1.159 (10)
Fe1—C2	2.096 (11)	Sn1—C16	2.166 (9)
Fe1—C1	2.103 (10)	Sn1—C14	2.174 (11)
Fe1—C3	2.104 (10)	Sn1—C12	2.177 (10)
Fe1—Sn1	2.5455 (13)	C12—C13	1.483 (16)
C1—C5	1.381 (16)	C12—H12A	0.9900
C1—C2	1.408 (19)	C12—H12B	0.9900
C1—H1A	0.9500	C13—H13A	0.9800
C2—C3	1.362 (19)	C13—H13B	0.9800
C2—H2A	0.9500	C13—H13C	0.9800
C3—C4	1.389 (15)	C14—C15	1.461 (17)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C5	1.372 (14)	C14—H14B	0.9900
C4—H4A	0.9500	C15—H15A	0.9800
C5—H5A	0.9500	C15—H15B	0.9800
N1—C10	1.341 (10)	C15—H15C	0.9800
N1—C6	1.343 (10)	C16—C17	1.471 (14)
C6—C7	1.371 (12)	C16—H16A	0.9900
C6—H6A	0.9500	C16—H16B	0.9900
C7—C8	1.364 (13)	C17—H17A	0.9800
C7—H7A	0.9500	C17—H17B	0.9800
C8—C9	1.362 (13)	C17—H17C	0.9800
C8—H8A	0.9500
C11—Fe1—N1	96.1 (3)	C6—N1—Fe1	121.9 (5)
C11—Fe1—C5	123.1 (4)	N1—C6—C7	124.0 (9)
N1—Fe1—C5	139.8 (4)	N1—C6—H6A	118.0
C11—Fe1—C4	95.2 (4)	C7—C6—H6A	118.0
N1—Fe1—C4	157.9 (4)	C8—C7—C6	118.9 (9)
C5—Fe1—C4	38.5 (4)	C8—C7—H7A	120.6
C11—Fe1—C2	136.0 (6)	C6—C7—H7A	120.6
N1—Fe1—C2	94.3 (4)	C9—C8—C7	118.8 (8)
C5—Fe1—C2	64.8 (5)	C9—C8—H8A	120.6
C4—Fe1—C2	64.6 (4)	C7—C8—H8A	120.6
C11—Fe1—C1	159.7 (4)	C8—C9—C10	119.2 (9)
N1—Fe1—C1	103.7 (4)	C8—C9—H9A	120.4
C5—Fe1—C1	38.5 (5)	C10—C9—H9A	120.4
C4—Fe1—C1	64.7 (4)	N1—C10—C9	123.5 (8)
C2—Fe1—C1	39.2 (5)	N1—C10—H10A	118.3
C11—Fe1—C3	102.0 (5)	C9—C10—H10A	118.3
N1—Fe1—C3	119.9 (4)	O1—C11—Fe1	178.3 (8)
C5—Fe1—C3	64.4 (4)	C16—Sn1—C14	105.3 (5)
C4—Fe1—C3	38.8 (4)	C16—Sn1—C12	105.9 (5)
C2—Fe1—C3	37.9 (5)	C14—Sn1—C12	105.5 (5)
C1—Fe1—C3	64.4 (5)	C16—Sn1—Fe1	111.9 (3)
C11—Fe1—Sn1	84.2 (3)	C14—Sn1—Fe1	112.1 (3)
N1—Fe1—Sn1	88.59 (19)	C12—Sn1—Fe1	115.3 (3)
C5—Fe1—Sn1	87.0 (3)	C13—C12—Sn1	117.3 (8)
C4—Fe1—Sn1	111.5 (3)	C13—C12—H12A	108.0
C2—Fe1—Sn1	138.8 (5)	Sn1—C12—H12A	108.0
C1—Fe1—Sn1	100.3 (4)	C13—C12—H12B	108.0
C3—Fe1—Sn1	149.5 (3)	Sn1—C12—H12B	108.0
C5—C1—C2	106.8 (11)	H12A—C12—H12B	107.2
C5—C1—Fe1	69.8 (6)	C12—C13—H13A	109.5
C2—C1—Fe1	70.1 (6)	C12—C13—H13B	109.5
C5—C1—H1A	126.6	H13A—C13—H13B	109.5
C2—C1—H1A	126.6	C12—C13—H13C	109.5
Fe1—C1—H1A	125.0	H13A—C13—H13C	109.5
C3—C2—C1	108.1 (11)	H13B—C13—H13C	109.5
C3—C2—Fe1	71.4 (7)	C15—C14—Sn1	117.2 (10)
C1—C2—Fe1	70.7 (6)	C15—C14—H14A	108.0
C3—C2—H2A	126.0	Sn1—C14—H14A	108.0
C1—C2—H2A	126.0	C15—C14—H14B	108.0
Fe1—C2—H2A	123.6	Sn1—C14—H14B	108.0
C2—C3—C4	108.5 (11)	H14A—C14—H14B	107.2
C2—C3—Fe1	70.8 (6)	C14—C15—H15A	109.5
C4—C3—Fe1	69.8 (6)	C14—C15—H15B	109.5
C2—C3—H3A	125.7	H15A—C15—H15B	109.5
C4—C3—H3A	125.7	C14—C15—H15C	109.5
Fe1—C3—H3A	125.3	H15A—C15—H15C	109.5
C5—C4—C3	107.7 (10)	H15B—C15—H15C	109.5
C5—C4—Fe1	70.7 (5)	C17—C16—Sn1	118.6 (8)
C3—C4—Fe1	71.5 (6)	C17—C16—H16A	107.7
C5—C4—H4A	126.2	Sn1—C16—H16A	107.7
C3—C4—H4A	126.2	C17—C16—H16B	107.7
Fe1—C4—H4A	123.4	Sn1—C16—H16B	107.7
C4—C5—C1	109.0 (10)	H16A—C16—H16B	107.1
C4—C5—Fe1	70.8 (5)	C16—C17—H17A	109.5
C1—C5—Fe1	71.6 (6)	C16—C17—H17B	109.5
C4—C5—H5A	125.5	H17A—C17—H17B	109.5
C1—C5—H5A	125.5	C16—C17—H17C	109.5
Fe1—C5—H5A	123.6	H17A—C17—H17C	109.5
C10—N1—C6	115.6 (7)	H17B—C17—H17C	109.5
C10—N1—Fe1	122.4 (5)
C11—Fe1—C1—C5	−30 (2)	N1—Fe1—C5—C4	−144.9 (6)
N1—Fe1—C1—C5	162.9 (6)	C2—Fe1—C5—C4	−80.2 (8)
C4—Fe1—C1—C5	−37.2 (6)	C1—Fe1—C5—C4	−118.5 (10)
C2—Fe1—C1—C5	−117.3 (10)	C3—Fe1—C5—C4	−38.1 (7)
C3—Fe1—C1—C5	−80.3 (7)	Sn1—Fe1—C5—C4	130.9 (7)
Sn1—Fe1—C1—C5	71.8 (7)	C11—Fe1—C5—C1	168.2 (8)
C11—Fe1—C1—C2	87.8 (18)	N1—Fe1—C5—C1	−26.3 (10)
N1—Fe1—C1—C2	−79.8 (8)	C4—Fe1—C5—C1	118.5 (10)
C5—Fe1—C1—C2	117.3 (10)	C2—Fe1—C5—C1	38.3 (8)
C4—Fe1—C1—C2	80.1 (8)	C3—Fe1—C5—C1	80.4 (9)
C3—Fe1—C1—C2	37.0 (7)	Sn1—Fe1—C5—C1	−110.6 (8)
Sn1—Fe1—C1—C2	−170.8 (7)	C11—Fe1—N1—C10	−19.8 (7)
C5—C1—C2—C3	−1.4 (12)	C5—Fe1—N1—C10	172.4 (7)
Fe1—C1—C2—C3	−61.9 (8)	C4—Fe1—N1—C10	100.5 (11)
C5—C1—C2—Fe1	60.5 (7)	C2—Fe1—N1—C10	117.3 (8)
C11—Fe1—C2—C3	−32.4 (10)	C1—Fe1—N1—C10	155.9 (7)
N1—Fe1—C2—C3	−135.8 (7)	C3—Fe1—N1—C10	87.8 (8)
C5—Fe1—C2—C3	80.0 (7)	Sn1—Fe1—N1—C10	−103.8 (6)
C4—Fe1—C2—C3	37.3 (6)	C11—Fe1—N1—C6	162.7 (7)
C1—Fe1—C2—C3	117.7 (10)	C5—Fe1—N1—C6	−5.1 (9)
Sn1—Fe1—C2—C3	131.4 (7)	C4—Fe1—N1—C6	−77.0 (11)
C11—Fe1—C2—C1	−150.1 (8)	C2—Fe1—N1—C6	−60.2 (8)
N1—Fe1—C2—C1	106.5 (8)	C1—Fe1—N1—C6	−21.6 (8)
C5—Fe1—C2—C1	−37.7 (7)	C3—Fe1—N1—C6	−89.7 (8)
C4—Fe1—C2—C1	−80.4 (7)	Sn1—Fe1—N1—C6	78.7 (6)
C3—Fe1—C2—C1	−117.7 (10)	C10—N1—C6—C7	0.0 (13)
Sn1—Fe1—C2—C1	13.8 (10)	Fe1—N1—C6—C7	177.7 (7)
C1—C2—C3—C4	1.7 (12)	N1—C6—C7—C8	−0.4 (15)
Fe1—C2—C3—C4	−59.8 (7)	C6—C7—C8—C9	0.4 (15)
C1—C2—C3—Fe1	61.5 (7)	C7—C8—C9—C10	0.0 (14)
C11—Fe1—C3—C2	157.6 (8)	C6—N1—C10—C9	0.4 (12)
N1—Fe1—C3—C2	53.3 (8)	Fe1—N1—C10—C9	−177.3 (7)
C5—Fe1—C3—C2	−81.3 (8)	C8—C9—C10—N1	−0.4 (14)
C4—Fe1—C3—C2	−119.1 (11)	C11—Fe1—Sn1—C16	−42.6 (4)
C1—Fe1—C3—C2	−38.3 (7)	N1—Fe1—Sn1—C16	53.7 (4)
Sn1—Fe1—C3—C2	−103.3 (11)	C5—Fe1—Sn1—C16	−166.2 (5)
C11—Fe1—C3—C4	−83.3 (7)	C4—Fe1—Sn1—C16	−135.9 (5)
N1—Fe1—C3—C4	172.4 (6)	C2—Fe1—Sn1—C16	148.6 (6)
C5—Fe1—C3—C4	37.9 (7)	C1—Fe1—Sn1—C16	157.4 (5)
C2—Fe1—C3—C4	119.1 (11)	C3—Fe1—Sn1—C16	−146.4 (9)
C1—Fe1—C3—C4	80.8 (8)	C11—Fe1—Sn1—C14	−160.6 (5)
Sn1—Fe1—C3—C4	15.8 (13)	N1—Fe1—Sn1—C14	−64.4 (4)
C2—C3—C4—C5	−1.3 (11)	C5—Fe1—Sn1—C14	75.7 (5)
Fe1—C3—C4—C5	−61.8 (7)	C4—Fe1—Sn1—C14	106.1 (5)
C2—C3—C4—Fe1	60.4 (7)	C2—Fe1—Sn1—C14	30.5 (6)
C11—Fe1—C4—C5	−140.1 (7)	C1—Fe1—Sn1—C14	39.3 (5)
N1—Fe1—C4—C5	99.5 (11)	C3—Fe1—Sn1—C14	95.5 (9)
C2—Fe1—C4—C5	80.8 (8)	C11—Fe1—Sn1—C12	78.7 (5)
C1—Fe1—C4—C5	37.3 (7)	N1—Fe1—Sn1—C12	174.9 (5)
C3—Fe1—C4—C5	117.2 (10)	C5—Fe1—Sn1—C12	−45.0 (6)
Sn1—Fe1—C4—C5	−54.3 (7)	C4—Fe1—Sn1—C12	−14.6 (5)
C11—Fe1—C4—C3	102.7 (8)	C2—Fe1—Sn1—C12	−90.2 (7)
N1—Fe1—C4—C3	−17.7 (14)	C1—Fe1—Sn1—C12	−81.4 (6)
C5—Fe1—C4—C3	−117.2 (10)	C3—Fe1—Sn1—C12	−25.2 (9)
C2—Fe1—C4—C3	−36.4 (8)	C16—Sn1—C12—C13	89.4 (10)
C1—Fe1—C4—C3	−80.0 (9)	C14—Sn1—C12—C13	−159.2 (10)
Sn1—Fe1—C4—C3	−171.5 (7)	Fe1—Sn1—C12—C13	−35.0 (11)
C3—C4—C5—C1	0.4 (11)	C16—Sn1—C14—C15	64.0 (12)
Fe1—C4—C5—C1	−61.8 (7)	C12—Sn1—C14—C15	−47.8 (12)
C3—C4—C5—Fe1	62.3 (7)	Fe1—Sn1—C14—C15	−174.1 (10)
C2—C1—C5—C4	0.6 (11)	C14—Sn1—C16—C17	−65.9 (11)
Fe1—C1—C5—C4	61.3 (7)	C12—Sn1—C16—C17	45.6 (11)
C2—C1—C5—Fe1	−60.7 (7)	Fe1—Sn1—C16—C17	172.0 (9)
C11—Fe1—C5—C4	49.7 (8)