Dicarbon-yl(hexa-methyl-ene-1,3,5,7-tetra-mine-κN(1))(η(5)-penta-methyl-cyclo-penta-dien-yl)iron(II) tetra-fluoridoborate.

In the title compound, [Fe(C(10)H(15))(C(6)H(12)N(4))(CO)(2)]BF(4), the arrangement around the Fe(II) atom corresponds to a three-legged piano stool. The penta-methyl-cyclo-penta-dienyl (Cp*) ligand occupies three coordination sites, while two CO ligands and one N atom of the hexa-methyl-ene-tetra-mine ligand occupy the remaining coordination sites, completing a pseudo-octahedral geometry. Both the complex cation and the BF(4) (-) anion reside on crystallographic mirror planes. The Fe-N bond length is 2.069 (2) and the Fe-Cp*(centroid) distance is 1.7452 (3) Å.

Related literature

For the synthesis of the title compound and structure of the dinuclear compound [Fe2(η5-C5H5)2{n class="Chemical">N4(CH2)6}(CO)4](BF4)2 see: M’thiruaine et al. (2012. For other related compounds, see: Allan et al. (1970 ▶); Darensbourg et al. (2003 ▶); Lu et al. (2004 ▶); Matos & Verkade (2003 ▶); M’thiruaine et al. (2012b ▶); Shafiq et al. (2000 ▶). For mol­ecular structures of other metal complexes of hexa­methyl­ene­tetra­mine, see: Zheng et al. (2008 ▶); Xue et al. (2009 ▶). For applications of hexa­methyl­ene­tetra­mine, see: Greenwood (1981 ▶); Strom & Jun (1986 ▶); Garcia et al. (2010 ▶).

Experimental

Crystal data

[Fe(C10H15)(n class="CellLine">C6H12N4)(CO)2]BF4

M = 474.10

Orthorhombic,

a = 13.8388 (6) Å

b = 9.1771 (4) Å

c = 16.4365 (8) Å

V = 2087.44 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 173 K

0.40 × 0.40 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: integration (SADABS; Bruker, 2005 ▶) T min = 0.746, T max = 0.746

16663 measured reflections

2671 independent reflections

2065 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.04

2671 reflections

153 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAIn class="Chemical">NT-Plus and XPREP (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026360/fj2565sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026360/fj2565Isup2.hkl

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

[Fe(C10H15)(C6H12N4)(CO)2]BF4	F(000) = 984
Mr = 474.10	Dx = 1.509 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4126 reflections
a = 13.8388 (6) Å	θ = 2.5–26.9°
b = 9.1771 (4) Å	µ = 0.78 mm−1
c = 16.4365 (8) Å	T = 173 K
V = 2087.44 (16) Å3	Block, brown
Z = 4	0.40 × 0.40 × 0.40 mm

Bruker APEXII CCD diffractometer	2671 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: integration (SADABS; Bruker, 2005)	h = −17→18
Tmin = 0.746, Tmax = 0.746	k = −12→12
16663 measured reflections	l = −14→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3
2671 reflections	(Δ/σ)max = 0.008
153 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Experimental. face indexed absorption corrections carried out with XPREP; Bruker, 2005)

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	Occ. (<1)
C1	−0.07473 (16)	0.7500	0.29615 (16)	0.0216 (5)
C2	−0.04858 (13)	0.8758 (2)	0.25029 (10)	0.0225 (4)
C3	−0.01373 (12)	0.82727 (19)	0.17274 (10)	0.0239 (4)
C4	−0.13130 (18)	0.7500	0.37414 (16)	0.0286 (6)
H4A	−0.1161	0.6660	0.4052	0.043*	0.50
H4B	−0.1985	0.7500	0.3629	0.043*
H4C	−0.1161	0.8340	0.4052	0.043*	0.50
C5	−0.06466 (14)	1.0313 (2)	0.27470 (13)	0.0304 (4)
H5A	−0.1229	1.0685	0.2478	0.046*
H5B	−0.0088	1.0900	0.2584	0.046*
H5C	−0.0728	1.0370	0.3338	0.046*
C6	0.00822 (15)	0.9225 (2)	0.10053 (12)	0.0351 (5)
H6A	0.0601	0.8783	0.0683	0.053*
H6B	0.0287	1.0190	0.1194	0.053*
H6C	−0.0499	0.9324	0.0668	0.053*
C7	0.15593 (13)	0.6020 (2)	0.23589 (11)	0.0263 (4)
C8	0.09551 (13)	0.61629 (18)	0.43011 (11)	0.0220 (4)
H8A	0.0240	0.6120	0.4298	0.026*
H8B	0.1200	0.5280	0.4023	0.026*
C9	0.23775 (17)	0.7500	0.38815 (15)	0.0238 (5)
H9A	0.2629	0.6628	0.3597	0.029*	0.50
H9B	0.2629	0.8372	0.3597	0.029*	0.50
C10	0.23601 (14)	0.61969 (19)	0.51331 (11)	0.0295 (4)
H10A	0.2601	0.6186	0.5700	0.035*
H10B	0.2606	0.5313	0.4857	0.035*
C11	0.0944 (2)	0.7500	0.55398 (16)	0.0278 (6)
H11A	0.1160	0.7500	0.6114	0.033*
H11B	0.0228	0.7500	0.5537	0.033*
B1	0.2554 (3)	0.2500	0.4092 (2)	0.0361 (8)
F1	0.28284 (11)	0.12563 (13)	0.36756 (8)	0.0570 (4)
F2	0.29634 (17)	0.2500	0.48627 (13)	0.0660 (6)
F3	0.15679 (15)	0.2500	0.41946 (15)	0.0703 (7)
Fe1	0.07875 (2)	0.7500	0.26471 (2)	0.01882 (12)
N1	0.12822 (14)	0.7500	0.38349 (12)	0.0187 (4)
N2	0.12944 (12)	0.61662 (15)	0.51387 (9)	0.0253 (3)
N3	0.27327 (16)	0.7500	0.47139 (13)	0.0269 (5)
O1	0.19858 (10)	0.50678 (17)	0.21102 (9)	0.0410 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0185 (12)	0.0302 (13)	0.0161 (12)	0.000	−0.0015 (9)	0.000
C2	0.0204 (9)	0.0277 (9)	0.0194 (9)	0.0024 (7)	−0.0024 (7)	0.0002 (7)
C3	0.0224 (9)	0.0318 (10)	0.0174 (9)	0.0007 (7)	−0.0027 (7)	0.0037 (7)
C4	0.0205 (13)	0.0430 (16)	0.0223 (14)	0.000	0.0035 (11)	0.000
C5	0.0316 (11)	0.0271 (9)	0.0326 (12)	0.0070 (8)	−0.0011 (8)	−0.0017 (8)
C6	0.0375 (11)	0.0463 (12)	0.0216 (10)	−0.0025 (9)	−0.0019 (8)	0.0118 (9)
C7	0.0247 (10)	0.0361 (10)	0.0182 (9)	0.0006 (8)	−0.0031 (7)	−0.0028 (8)
C8	0.0296 (10)	0.0189 (8)	0.0177 (9)	−0.0013 (7)	−0.0010 (7)	0.0008 (7)
C9	0.0197 (12)	0.0320 (13)	0.0198 (13)	0.000	−0.0020 (10)	0.000
C10	0.0377 (11)	0.0289 (10)	0.0219 (10)	0.0049 (8)	−0.0073 (8)	0.0024 (8)
C11	0.0410 (16)	0.0265 (13)	0.0158 (13)	0.000	0.0015 (11)	0.000
B1	0.045 (2)	0.0277 (15)	0.036 (2)	0.000	0.0101 (15)	0.000
F1	0.0836 (11)	0.0364 (7)	0.0509 (9)	0.0058 (7)	0.0261 (7)	−0.0094 (6)
F2	0.0916 (17)	0.0588 (13)	0.0476 (13)	0.000	−0.0102 (12)	0.000
F3	0.0478 (13)	0.0654 (14)	0.0979 (19)	0.000	0.0209 (12)	0.000
Fe1	0.0191 (2)	0.02309 (19)	0.01423 (19)	0.000	0.00091 (13)	0.000
N1	0.0216 (10)	0.0195 (10)	0.0151 (10)	0.000	0.0006 (8)	0.000
N2	0.0361 (9)	0.0220 (7)	0.0178 (8)	0.0003 (6)	−0.0030 (6)	0.0009 (6)
N3	0.0295 (12)	0.0298 (11)	0.0213 (11)	0.000	−0.0066 (9)	0.000
O1	0.0396 (8)	0.0480 (9)	0.0354 (8)	0.0173 (7)	−0.0028 (7)	−0.0147 (7)

C1—C2	1.425 (2)	C8—H8B	0.9900
C1—C2i	1.425 (2)	C9—N3	1.454 (3)
C1—C4	1.502 (3)	C9—N1	1.518 (3)
C1—Fe1	2.186 (2)	C9—H9A	0.9900
C2—C3	1.434 (2)	C9—H9B	0.9900
C2—C5	1.499 (2)	C10—N3	1.473 (2)
C2—Fe1	2.1199 (18)	C10—N2	1.475 (3)
C3—C3i	1.418 (3)	C10—H10A	0.9900
C3—C6	1.505 (2)	C10—H10B	0.9900
C3—Fe1	2.1038 (17)	C11—N2	1.473 (2)
C4—H4A	0.9482	C11—N2i	1.473 (2)
C4—H4B	0.9477	C11—H11A	0.9900
C4—H4C	0.9482	C11—H11B	0.9900
C5—H5A	0.9800	B1—F3	1.375 (4)
C5—H5B	0.9800	B1—F1ii	1.384 (2)
C5—H5C	0.9800	B1—F1	1.384 (2)
C6—H6A	0.9800	B1—F2	1.388 (4)
C6—H6B	0.9800	Fe1—C7i	1.791 (2)
C6—H6C	0.9800	Fe1—N1	2.069 (2)
C7—O1	1.131 (2)	Fe1—C3i	2.1038 (17)
C7—Fe1	1.791 (2)	Fe1—C2i	2.1199 (18)
C8—N2	1.455 (2)	N1—C8i	1.516 (2)
C8—N1	1.516 (2)	N3—C10i	1.473 (2)
C8—H8A	0.9900
C2—C1—C2i	108.2 (2)	H10A—C10—H10B	108.0
C2—C1—C4	125.70 (11)	N2—C11—N2i	112.4 (2)
C2i—C1—C4	125.70 (11)	N2—C11—H11A	109.1
C2—C1—Fe1	68.18 (12)	N2i—C11—H11A	109.1
C2i—C1—Fe1	68.18 (12)	N2—C11—H11B	109.1
C4—C1—Fe1	135.09 (18)	N2i—C11—H11B	109.1
C1—C2—C3	107.69 (16)	H11A—C11—H11B	107.8
C1—C2—C5	126.29 (17)	F3—B1—F1ii	109.5 (2)
C3—C2—C5	125.70 (16)	F3—B1—F1	109.5 (2)
C1—C2—Fe1	73.19 (12)	F1ii—B1—F1	111.1 (3)
C3—C2—Fe1	69.55 (10)	F3—B1—F2	107.1 (3)
C5—C2—Fe1	127.73 (13)	F1ii—B1—F2	109.8 (2)
C3i—C3—C2	108.09 (10)	F1—B1—F2	109.8 (2)
C3i—C3—C6	125.52 (11)	C7—Fe1—C7i	98.58 (12)
C2—C3—C6	126.05 (16)	C7—Fe1—N1	93.00 (7)
C3i—C3—Fe1	70.30 (5)	C7i—Fe1—N1	93.00 (7)
C2—C3—Fe1	70.76 (10)	C7—Fe1—C3i	85.25 (8)
C6—C3—Fe1	129.76 (13)	C7i—Fe1—C3i	115.35 (8)
C1—C4—H4A	110.1	N1—Fe1—C3i	151.56 (6)
C1—C4—H4B	110.2	C7—Fe1—C3	115.35 (8)
H4A—C4—H4B	108.8	C7i—Fe1—C3	85.25 (8)
C1—C4—H4C	110.1	N1—Fe1—C3	151.56 (6)
H4A—C4—H4C	108.8	C3i—Fe1—C3	39.40 (10)
H4B—C4—H4C	108.8	C7—Fe1—C2i	93.05 (8)
C2—C5—H5A	109.5	C7i—Fe1—C2i	151.50 (8)
C2—C5—H5B	109.5	N1—Fe1—C2i	112.37 (7)
H5A—C5—H5B	109.5	C3i—Fe1—C2i	39.69 (7)
C2—C5—H5C	109.5	C3—Fe1—C2i	66.27 (7)
H5A—C5—H5C	109.5	C7—Fe1—C2	151.50 (8)
H5B—C5—H5C	109.5	C7i—Fe1—C2	93.05 (8)
C3—C6—H6A	109.5	N1—Fe1—C2	112.37 (7)
C3—C6—H6B	109.5	C3i—Fe1—C2	66.27 (7)
H6A—C6—H6B	109.5	C3—Fe1—C2	39.69 (7)
C3—C6—H6C	109.5	C2i—Fe1—C2	65.99 (10)
H6A—C6—H6C	109.5	C7—Fe1—C1	129.93 (6)
H6B—C6—H6C	109.5	C7i—Fe1—C1	129.93 (6)
O1—C7—Fe1	172.94 (17)	N1—Fe1—C1	95.65 (9)
N2—C8—N1	112.36 (14)	C3i—Fe1—C1	65.09 (8)
N2—C8—H8A	109.1	C3—Fe1—C1	65.09 (8)
N1—C8—H8A	109.1	C2i—Fe1—C1	38.62 (6)
N2—C8—H8B	109.1	C2—Fe1—C1	38.62 (6)
N1—C8—H8B	109.1	C8i—N1—C8	108.09 (18)
H8A—C8—H8B	107.9	C8i—N1—C9	105.83 (12)
N3—C9—N1	112.7 (2)	C8—N1—C9	105.83 (12)
N3—C9—H9A	109.1	C8i—N1—Fe1	112.22 (10)
N1—C9—H9A	109.1	C8—N1—Fe1	112.22 (10)
N3—C9—H9B	109.1	C9—N1—Fe1	112.21 (14)
N1—C9—H9B	109.1	C8—N2—C11	108.61 (16)
H9A—C9—H9B	107.8	C8—N2—C10	108.47 (14)
N3—C10—N2	111.61 (15)	C11—N2—C10	108.45 (16)
N3—C10—H10A	109.3	C9—N3—C10i	108.77 (13)
N2—C10—H10A	109.3	C9—N3—C10	108.77 (13)
N3—C10—H10B	109.3	C10i—N3—C10	108.5 (2)
N2—C10—H10B	109.3
C2i—C1—C2—C3	4.9 (3)	C2i—C1—Fe1—C7	−20.56 (17)
C4—C1—C2—C3	−168.0 (2)	C4—C1—Fe1—C7	98.70 (10)
Fe1—C1—C2—C3	61.35 (13)	C2—C1—Fe1—C7i	20.56 (17)
C2i—C1—C2—C5	178.72 (12)	C2i—C1—Fe1—C7i	142.04 (11)
C4—C1—C2—C5	5.8 (4)	C4—C1—Fe1—C7i	−98.70 (10)
Fe1—C1—C2—C5	−124.84 (19)	C2—C1—Fe1—N1	119.26 (11)
C2i—C1—C2—Fe1	−56.44 (17)	C2i—C1—Fe1—N1	−119.26 (11)
C4—C1—C2—Fe1	130.7 (2)	C4—C1—Fe1—N1	0.0
C1—C2—C3—C3i	−3.03 (16)	C2—C1—Fe1—C3i	−82.56 (13)
C5—C2—C3—C3i	−176.89 (15)	C2i—C1—Fe1—C3i	38.92 (11)
Fe1—C2—C3—C3i	60.69 (12)	C4—C1—Fe1—C3i	158.18 (5)
C1—C2—C3—C6	170.56 (18)	C2—C1—Fe1—C3	−38.92 (11)
C5—C2—C3—C6	−3.3 (3)	C2i—C1—Fe1—C3	82.56 (13)
Fe1—C2—C3—C6	−125.73 (18)	C4—C1—Fe1—C3	−158.18 (5)
C1—C2—C3—Fe1	−63.71 (14)	C2—C1—Fe1—C2i	−121.5 (2)
C5—C2—C3—Fe1	122.43 (19)	C4—C1—Fe1—C2i	119.26 (11)
C3i—C3—Fe1—C7	43.83 (7)	C2i—C1—Fe1—C2	121.5 (2)
C2—C3—Fe1—C7	162.15 (11)	C4—C1—Fe1—C2	−119.26 (11)
C6—C3—Fe1—C7	−76.48 (19)	N2—C8—N1—C8i	−55.2 (2)
C3i—C3—Fe1—C7i	141.10 (6)	N2—C8—N1—C9	57.82 (19)
C2—C3—Fe1—C7i	−100.59 (12)	N2—C8—N1—Fe1	−179.48 (11)
C6—C3—Fe1—C7i	20.78 (18)	N3—C9—N1—C8i	57.29 (11)
C3i—C3—Fe1—N1	−131.39 (13)	N3—C9—N1—C8	−57.29 (11)
C2—C3—Fe1—N1	−13.07 (18)	N3—C9—N1—Fe1	180.0
C6—C3—Fe1—N1	108.29 (19)	C7—Fe1—N1—C8i	168.40 (13)
C2—C3—Fe1—C3i	118.32 (9)	C7i—Fe1—N1—C8i	69.64 (13)
C6—C3—Fe1—C3i	−120.32 (16)	C3i—Fe1—N1—C8i	−106.04 (13)
C3i—C3—Fe1—C2i	−37.89 (6)	C3—Fe1—N1—C8i	−15.9 (2)
C2—C3—Fe1—C2i	80.43 (14)	C2i—Fe1—N1—C8i	−97.06 (12)
C6—C3—Fe1—C2i	−158.20 (19)	C2—Fe1—N1—C8i	−24.90 (14)
C3i—C3—Fe1—C2	−118.32 (9)	C1—Fe1—N1—C8i	−60.98 (12)
C6—C3—Fe1—C2	121.4 (2)	C7—Fe1—N1—C8	−69.64 (13)
C3i—C3—Fe1—C1	−80.43 (9)	C7i—Fe1—N1—C8	−168.40 (13)
C2—C3—Fe1—C1	37.89 (9)	C3i—Fe1—N1—C8	15.9 (2)
C6—C3—Fe1—C1	159.25 (19)	C3—Fe1—N1—C8	106.04 (13)
C1—C2—Fe1—C7	81.4 (2)	C2i—Fe1—N1—C8	24.90 (14)
C3—C2—Fe1—C7	−35.5 (2)	C2—Fe1—N1—C8	97.06 (12)
C5—C2—Fe1—C7	−155.42 (17)	C1—Fe1—N1—C8	60.98 (12)
C1—C2—Fe1—C7i	−164.35 (13)	C7—Fe1—N1—C9	49.38 (6)
C3—C2—Fe1—C7i	78.81 (12)	C7i—Fe1—N1—C9	−49.38 (6)
C5—C2—Fe1—C7i	−41.12 (17)	C3i—Fe1—N1—C9	134.94 (12)
C1—C2—Fe1—N1	−69.85 (12)	C3—Fe1—N1—C9	−134.94 (12)
C3—C2—Fe1—N1	173.31 (9)	C2i—Fe1—N1—C9	143.92 (6)
C5—C2—Fe1—N1	53.38 (17)	C2—Fe1—N1—C9	−143.92 (6)
C1—C2—Fe1—C3i	79.22 (12)	C1—Fe1—N1—C9	180.0
C3—C2—Fe1—C3i	−37.62 (11)	N1—C8—N2—C11	57.6 (2)
C5—C2—Fe1—C3i	−157.54 (18)	N1—C8—N2—C10	−60.06 (18)
C1—C2—Fe1—C3	116.84 (16)	N2i—C11—N2—C8	−60.0 (3)
C5—C2—Fe1—C3	−119.9 (2)	N2i—C11—N2—C10	57.7 (2)
C1—C2—Fe1—C2i	35.65 (13)	N3—C10—N2—C8	59.72 (18)
C3—C2—Fe1—C2i	−81.19 (10)	N3—C10—N2—C11	−58.1 (2)
C5—C2—Fe1—C2i	158.88 (14)	N1—C9—N3—C10i	−59.01 (14)
C3—C2—Fe1—C1	−116.84 (16)	N1—C9—N3—C10	59.01 (14)
C5—C2—Fe1—C1	123.2 (2)	N2—C10—N3—C9	−59.2 (2)
C2—C1—Fe1—C7	−142.04 (11)	N2—C10—N3—C10i	59.0 (2)