2,2′-Bis(4-methoxy­phen­yl)-2,2′-bis­(tri­methyl­silan­yloxy)-2,2′-(ferrocene-1,1′-diyl)diacetonitrile

Wang, X.; Bao, H.

doi:10.1107/S1600536807064513

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m123

https://doi.org/10.1107/S1600536807064513

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2,2′-Bis(4-methoxyphenyl)-2,2′-bis(trimethylsilanyloxy)-2,2′-(ferrocene-1,1′-diyl)diacetonitrile

Xiao-li Wang ^a and Huaying Bao ^a ^*

^aCollege of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China
^*Correspondence e-mail: hxxwangxiaoli@163.com

(Received 8 November 2007; accepted 29 November 2007; online 6 December 2007)

In the title compound, [Fe(C₁₇H₂₀NO₂Si)₂], the Fe atom is situated on a crystallographic centre of inversion, leading to a perfectly staggered conformation of the Cp rings.

Related literature

For related literature, see: Evans & Truesdale (1973 ); Evans et al. (1974 ); Lidy & Sundermeyer (1973 ); Dunitz et al. (1956 ); Fischer & Hüning (1987 ); Fleming & Woolias (1979 ); Gassman & Talley (1978 ); Groutas & Felker (1980 ); Rasmussen & Heilmann (1978 ); Zhou (1989 ).

Experimental

Crystal data

[Fe(C₁₇H₂₀NO₂Si)₂]
M_r = 652.71
Triclinic, $[P \overline 1]$
a = 7.129 (2) Å
b = 10.500 (4) Å
c = 11.449 (4) Å
α = 95.613 (5)°
β = 97.253 (6)°
γ = 97.441 (6)°
V = 837.3 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 (2) K
0.24 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.822, T_max = 1.000 (expected range = 0.768–0.935)
4803 measured reflections
3367 independent reflections
2156 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.204
S = 1.03
3367 reflections
196 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: SHELXTL (Bruker, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064513/im2048sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064513/im2048Isup2.hkl

checkCIF report

Comment top

Cyanohydrin trimethylsilyl ethers are useful in organic synthesis as they serve not only for the protection of carbonyl groups (Rasmussen et al., 1978; Groutas et al., 1980; Fischer et al., 1987) but also as versatile intermediates (Gassman et al., 1978; Evans et al., 1974; Fleming et al., 1979) in the synthesis of cyanohydrins, α,β-unsaturated nitriles and β-aminoalcohols. The general method for the preparation of cyanohydrin trimethylsilyl ethers is the addition of trimethylsilyl cyanide (TMSCN) to carbonyl compounds with the aid of a catalyst including Lewis acids, such as ZnI₂ (Evans et al.,1974) and AlCl₃ (Lidy et al., 1973), as well as solubilized anionic species, such as K⁺CN^--18-Crown-6 and ⁿBu₄N⁺CN^- (Evans et al.,1973).

The molecular structure of the title compound, (I), shows the Fe atom on a crystallographic center of inversion and two Cp ligands with a cyanohydrin ether substituents. Because of the inversion symmetry the Cp ligands show a staggered conformation. The central tetrahedral C(6) atom is bound to C≡N, (CH₃)₃SiO and (CH₃O)C₆H₄ groups in compound and is therefore a new stereogenic center which is formed during the reaction sequence. Due to the internal symmetry of the molecule Figure 1 shows the R,S diastereomer. There is no evidence for the formation of R,R- or S,S-diastereomers even from NMR spectra of the crude reaction product. The bond angle of C(6)–C(7)–N(1) is 178.9 (6)° showing sp hybridization for the C≡N carbon atom. The Si(1)—O(1)—C(6) bond angle measures to 131.6 (3)° which is significantly larger compared to that of a regular tetrahedron (109.5°). The influence of neighbouring Csp and Csp² atoms shorten the C(6)–C(1), C(6)–C(7) and C(6)–C(8) bond distances (1.511 (6) Å, 1.483 (7) Å and 1.531 (6), respectively) compared to normal C—C bond distances (app. 1.54 Å). It shows there may be a super conjugate effect in the molecule of the title compound.

Related literature top

For related literature, see: Evans & Truesdale (1973); Evans et al. (1974); Lidy & Sundermeyer (1973); Dunitz et al. (1956); Fischer & Hüning (1987); Fleming & Woolias (1979); Gassman & Talley (1978); Groutas & Felker (1980); Rasmussen & Heilmann (1978); Zhou (1989).

Experimental top

Into a 100 ml 3-neck round-bottomed flask equipped with magnetic stirring bar, reflux condenser and CaCl₂ drying tube was placed 1.1 mmol (297 mg) bisacetylferrocene in 15 ml dry CH₂Cl₂ and 1 mmol (319 mg) ZnI₂. After stirring for 20 minutes, 4.4 mmol TMSCN (374 mg) were added and the was solution stirred for 10 h. During the reaction the progress of the reaction was monitored by TLC (benzene). After completion the solvent was evaporated under reduced pressure with the residue obtained being extracted with pentane. The solution was washed with saturated cold aqueous NaHSO₃ and dried over Na₂SO₄. Filtration and removal of the solvent under reduced pressure yielded the crude product which was recrystallized from ether/light petroleum (b.p. 60–90°) to obtain single crystals the title compound.

Structure description top

For related literature, see: Evans & Truesdale (1973); Evans et al. (1974); Lidy & Sundermeyer (1973); Dunitz et al. (1956); Fischer & Hüning (1987); Fleming & Woolias (1979); Gassman & Talley (1978); Groutas & Felker (1980); Rasmussen & Heilmann (1978); Zhou (1989).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented by circles of arbitrary size.

2,2'-Bis(4-methoxyphenyl)-2,2'-bis(trimethylsilanyloxy)-2,2'-(ferrocene-1,1'- diyl)diacetonitrile top

Crystal data top

[Fe(C₁₇H₂₀NO₂Si)₂]	Z = 1
M_r = 652.71	F(000) = 344
Triclinic, P1	D_x = 1.295 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.129 (2) Å	Cell parameters from 749 reflections
b = 10.500 (4) Å	θ = 2.5–25.4°
c = 11.449 (4) Å	µ = 0.56 mm⁻¹
α = 95.613 (5)°	T = 293 K
β = 97.253 (6)°	Needle, yellow
γ = 97.441 (6)°	0.24 × 0.14 × 0.12 mm
V = 837.3 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3367 independent reflections
Radiation source: fine-focus sealed tube	2156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −7→8
T_min = 0.822, T_max = 1.000	k = −10→13
4803 measured reflections	l = −14→14

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.111P)² + 0.2987P] where P = (F_o² + 2F_c²)/3
3367 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.98 e Å⁻³
21 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Fe(C₁₇H₂₀NO₂Si)₂]	γ = 97.441 (6)°
M_r = 652.71	V = 837.3 (5) Å³
Triclinic, P1	Z = 1
a = 7.129 (2) Å	Mo Kα radiation
b = 10.500 (4) Å	µ = 0.56 mm⁻¹
c = 11.449 (4) Å	T = 293 K
α = 95.613 (5)°	0.24 × 0.14 × 0.12 mm
β = 97.253 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2156 reflections with I > 2σ(I)
T_min = 0.822, T_max = 1.000	R_int = 0.030
4803 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	21 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.03	Δρ_max = 0.98 e Å⁻³
3367 reflections	Δρ_min = −0.43 e Å⁻³
196 parameters

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
Fe2	1.0000	0.0000	0.0000	0.0414 (3)
Si1	1.0979 (2)	0.43619 (14)	0.25558 (15)	0.0644 (5)
N1	0.6209 (8)	0.2641 (6)	0.0446 (5)	0.0789 (15)
O1	1.0478 (5)	0.2772 (3)	0.2175 (3)	0.0539 (9)
O2	0.6132 (6)	0.1608 (4)	0.6498 (3)	0.0687 (11)
C1	0.9125 (6)	0.0596 (4)	0.1571 (4)	0.0410 (10)
C2	1.0873 (7)	0.0084 (5)	0.1784 (4)	0.0480 (11)
H2	1.2020	0.0520	0.2196	0.058*
C3	1.0536 (9)	−0.1225 (5)	0.1245 (4)	0.0597 (14)
H3	1.1433	−0.1794	0.1250	0.072*
C4	0.8633 (10)	−0.1509 (5)	0.0708 (4)	0.0635 (16)
H4	0.8054	−0.2297	0.0294	0.076*
C5	0.7750 (8)	−0.0411 (5)	0.0897 (4)	0.0532 (13)
H5	0.6483	−0.0343	0.0630	0.064*
C6	0.8760 (6)	0.1923 (4)	0.2043 (4)	0.0423 (10)
C7	0.7336 (8)	0.2337 (5)	0.1153 (4)	0.0544 (13)
C8	0.7960 (6)	0.1835 (4)	0.3217 (4)	0.0416 (10)
C9	0.9140 (7)	0.1609 (5)	0.4202 (4)	0.0521 (12)
H9	1.0403	0.1511	0.4138	0.063*
C10	0.8494 (7)	0.1524 (5)	0.5273 (4)	0.0538 (12)
H10	0.9319	0.1371	0.5924	0.065*
C11	0.6624 (7)	0.1664 (5)	0.5393 (4)	0.0492 (12)
C12	0.5414 (7)	0.1855 (5)	0.4407 (4)	0.0543 (12)
H12	0.4139	0.1919	0.4462	0.065*
C13	0.6097 (7)	0.1950 (5)	0.3340 (4)	0.0503 (12)
H13	0.5272	0.2096	0.2686	0.060*
C14	0.4225 (9)	0.1780 (7)	0.6651 (5)	0.0824 (19)
H14A	0.4054	0.1719	0.7463	0.124*
H14B	0.3345	0.1121	0.6148	0.124*
H14C	0.3989	0.2615	0.6446	0.124*
C15	1.2315 (13)	0.4614 (8)	0.4056 (7)	0.122 (3)
H15A	1.3430	0.4189	0.4066	0.183*
H15B	1.1520	0.4262	0.4598	0.183*
H15C	1.2695	0.5523	0.4291	0.183*
C16	0.8845 (10)	0.5181 (7)	0.2564 (7)	0.098 (2)
H16A	0.8091	0.4851	0.3136	0.146*
H16B	0.8101	0.5025	0.1792	0.146*
H16C	0.9232	0.6094	0.2770	0.146*
C17	1.2491 (13)	0.4952 (9)	0.1477 (8)	0.133 (3)
H17A	1.3593	0.4512	0.1500	0.200*
H17B	1.2894	0.5865	0.1671	0.200*
H17C	1.1776	0.4788	0.0695	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe2	0.0614 (7)	0.0322 (5)	0.0294 (5)	−0.0005 (4)	0.0117 (4)	0.0011 (3)
Si1	0.0751 (11)	0.0402 (8)	0.0728 (10)	−0.0016 (7)	0.0095 (8)	−0.0043 (7)
N1	0.084 (4)	0.087 (4)	0.070 (3)	0.018 (3)	0.012 (3)	0.025 (3)
O1	0.055 (2)	0.0387 (17)	0.066 (2)	−0.0051 (14)	0.0222 (16)	−0.0050 (15)
O2	0.083 (3)	0.082 (3)	0.050 (2)	0.017 (2)	0.0323 (19)	0.0128 (19)
C1	0.049 (3)	0.040 (2)	0.034 (2)	0.0011 (19)	0.0119 (19)	0.0049 (18)
C2	0.066 (3)	0.049 (3)	0.030 (2)	0.012 (2)	0.007 (2)	0.0025 (19)
C3	0.099 (5)	0.047 (3)	0.042 (3)	0.025 (3)	0.025 (3)	0.011 (2)
C4	0.113 (5)	0.034 (3)	0.042 (3)	−0.008 (3)	0.026 (3)	0.003 (2)
C5	0.061 (3)	0.050 (3)	0.042 (2)	−0.016 (2)	0.012 (2)	0.003 (2)
C6	0.046 (3)	0.039 (2)	0.040 (2)	−0.0013 (19)	0.014 (2)	−0.0024 (18)
C7	0.069 (3)	0.054 (3)	0.048 (3)	0.017 (3)	0.023 (3)	0.017 (2)
C8	0.048 (3)	0.038 (2)	0.038 (2)	0.0016 (19)	0.009 (2)	−0.0005 (18)
C9	0.045 (3)	0.060 (3)	0.054 (3)	0.012 (2)	0.015 (2)	0.002 (2)
C10	0.060 (3)	0.061 (3)	0.042 (3)	0.013 (2)	0.009 (2)	0.004 (2)
C11	0.062 (3)	0.044 (3)	0.043 (2)	0.003 (2)	0.023 (2)	0.000 (2)
C12	0.047 (3)	0.063 (3)	0.057 (3)	0.013 (2)	0.019 (2)	0.007 (2)
C13	0.042 (3)	0.062 (3)	0.047 (3)	0.008 (2)	0.008 (2)	0.007 (2)
C14	0.092 (5)	0.092 (5)	0.076 (4)	0.016 (4)	0.053 (4)	0.018 (3)
C15	0.136 (5)	0.096 (4)	0.122 (5)	0.017 (4)	−0.015 (4)	−0.007 (4)
C16	0.101 (4)	0.079 (4)	0.112 (4)	0.022 (3)	0.012 (3)	−0.001 (3)
C17	0.141 (5)	0.118 (5)	0.143 (5)	−0.004 (4)	0.045 (4)	0.023 (4)

Geometric parameters (Å, º) top

Fe2—C5	2.034 (5)	C4—H4	0.9300
Fe2—C5ⁱ	2.034 (5)	C5—H5	0.9300
Fe2—C4	2.042 (5)	C6—C7	1.483 (7)
Fe2—C4ⁱ	2.042 (5)	C6—C8	1.531 (6)
Fe2—C1	2.044 (4)	C8—C13	1.373 (6)
Fe2—C1ⁱ	2.044 (4)	C8—C9	1.379 (6)
Fe2—C3	2.045 (5)	C9—C10	1.370 (6)
Fe2—C3ⁱ	2.045 (5)	C9—H9	0.9300
Fe2—C2	2.048 (4)	C10—C11	1.382 (7)
Fe2—C2ⁱ	2.048 (4)	C10—H10	0.9300
Si1—O1	1.663 (3)	C11—C12	1.378 (7)
Si1—C15	1.833 (7)	C12—C13	1.378 (6)
Si1—C17	1.841 (8)	C12—H12	0.9300
Si1—C16	1.842 (7)	C13—H13	0.9300
N1—C7	1.164 (7)	C14—H14A	0.9600
O1—C6	1.401 (5)	C14—H14B	0.9600
O2—C11	1.360 (5)	C14—H14C	0.9600
O2—C14	1.425 (7)	C15—H15A	0.9600
C1—C2	1.422 (7)	C15—H15B	0.9600
C1—C5	1.433 (6)	C15—H15C	0.9600
C1—C6	1.511 (6)	C16—H16A	0.9600
C2—C3	1.428 (7)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.399 (8)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.395 (8)	C17—H17C	0.9600

C5—Fe2—C5ⁱ	180.0 (3)	C4—C3—Fe2	69.9 (3)
C5—Fe2—C4	40.0 (2)	C2—C3—Fe2	69.7 (3)
C5ⁱ—Fe2—C4	140.0 (2)	C4—C3—H3	125.7
C5—Fe2—C4ⁱ	140.0 (2)	C2—C3—H3	125.7
C5ⁱ—Fe2—C4ⁱ	40.0 (2)	Fe2—C3—H3	126.3
C4—Fe2—C4ⁱ	180.0 (3)	C5—C4—C3	108.5 (4)
C5—Fe2—C1	41.15 (17)	C5—C4—Fe2	69.7 (3)
C5ⁱ—Fe2—C1	138.85 (17)	C3—C4—Fe2	70.1 (3)
C4—Fe2—C1	68.36 (18)	C5—C4—H4	125.8
C4ⁱ—Fe2—C1	111.64 (18)	C3—C4—H4	125.8
C5—Fe2—C1ⁱ	138.85 (17)	Fe2—C4—H4	126.0
C5ⁱ—Fe2—C1ⁱ	41.15 (17)	C4—C5—C1	108.5 (5)
C4—Fe2—C1ⁱ	111.64 (18)	C4—C5—Fe2	70.3 (3)
C4ⁱ—Fe2—C1ⁱ	68.36 (18)	C1—C5—Fe2	69.8 (2)
C1—Fe2—C1ⁱ	180.00 (11)	C4—C5—H5	125.8
C5—Fe2—C3	67.6 (2)	C1—C5—H5	125.8
C5ⁱ—Fe2—C3	112.4 (2)	Fe2—C5—H5	125.7
C4—Fe2—C3	40.0 (2)	O1—C6—C7	109.7 (4)
C4ⁱ—Fe2—C3	140.0 (2)	O1—C6—C1	108.4 (4)
C1—Fe2—C3	68.23 (19)	C7—C6—C1	107.3 (4)
C1ⁱ—Fe2—C3	111.77 (19)	O1—C6—C8	112.2 (3)
C5—Fe2—C3ⁱ	112.4 (2)	C7—C6—C8	110.0 (4)
C5ⁱ—Fe2—C3ⁱ	67.6 (2)	C1—C6—C8	108.9 (4)
C4—Fe2—C3ⁱ	140.0 (2)	N1—C7—C6	178.9 (6)
C4ⁱ—Fe2—C3ⁱ	40.0 (2)	C13—C8—C9	117.6 (4)
C1—Fe2—C3ⁱ	111.77 (19)	C13—C8—C6	123.2 (4)
C1ⁱ—Fe2—C3ⁱ	68.23 (19)	C9—C8—C6	119.2 (4)
C3—Fe2—C3ⁱ	180.0 (4)	C10—C9—C8	121.5 (4)
C5—Fe2—C2	68.5 (2)	C10—C9—H9	119.3
C5ⁱ—Fe2—C2	111.5 (2)	C8—C9—H9	119.3
C4—Fe2—C2	68.3 (2)	C9—C10—C11	120.5 (5)
C4ⁱ—Fe2—C2	111.7 (2)	C9—C10—H10	119.8
C1—Fe2—C2	40.67 (18)	C11—C10—H10	119.8
C1ⁱ—Fe2—C2	139.33 (18)	O2—C11—C12	125.1 (5)
C3—Fe2—C2	40.83 (19)	O2—C11—C10	116.2 (5)
C3ⁱ—Fe2—C2	139.17 (19)	C12—C11—C10	118.7 (4)
C5—Fe2—C2ⁱ	111.5 (2)	C13—C12—C11	120.0 (4)
C5ⁱ—Fe2—C2ⁱ	68.5 (2)	C13—C12—H12	120.0
C4—Fe2—C2ⁱ	111.7 (2)	C11—C12—H12	120.0
C4ⁱ—Fe2—C2ⁱ	68.3 (2)	C8—C13—C12	121.8 (5)
C1—Fe2—C2ⁱ	139.33 (18)	C8—C13—H13	119.1
C1ⁱ—Fe2—C2ⁱ	40.67 (18)	C12—C13—H13	119.1
C3—Fe2—C2ⁱ	139.17 (19)	O2—C14—H14A	109.5
C3ⁱ—Fe2—C2ⁱ	40.83 (19)	O2—C14—H14B	109.5
C2—Fe2—C2ⁱ	180.00 (7)	H14A—C14—H14B	109.5
O1—Si1—C15	107.0 (3)	O2—C14—H14C	109.5
O1—Si1—C17	105.0 (3)	H14A—C14—H14C	109.5
C15—Si1—C17	110.9 (4)	H14B—C14—H14C	109.5
O1—Si1—C16	113.7 (3)	Si1—C15—H15A	109.5
C15—Si1—C16	108.6 (4)	Si1—C15—H15B	109.5
C17—Si1—C16	111.7 (4)	H15A—C15—H15B	109.5
C6—O1—Si1	131.6 (3)	Si1—C15—H15C	109.5
C11—O2—C14	117.4 (4)	H15A—C15—H15C	109.5
C2—C1—C5	107.2 (4)	H15B—C15—H15C	109.5
C2—C1—C6	126.1 (4)	Si1—C16—H16A	109.5
C5—C1—C6	126.6 (4)	Si1—C16—H16B	109.5
C2—C1—Fe2	69.8 (2)	H16A—C16—H16B	109.5
C5—C1—Fe2	69.0 (2)	Si1—C16—H16C	109.5
C6—C1—Fe2	129.5 (3)	H16A—C16—H16C	109.5
C1—C2—C3	107.2 (4)	H16B—C16—H16C	109.5
C1—C2—Fe2	69.5 (2)	Si1—C17—H17A	109.5
C3—C2—Fe2	69.5 (3)	Si1—C17—H17B	109.5
C1—C2—H2	126.4	H17A—C17—H17B	109.5
C3—C2—H2	126.4	Si1—C17—H17C	109.5
Fe2—C2—H2	126.2	H17A—C17—H17C	109.5
C4—C3—C2	108.6 (5)	H17B—C17—H17C	109.5

C15—Si1—O1—C6	108.2 (5)	C4ⁱ—Fe2—C4—C5	17 (100)
C17—Si1—O1—C6	−134.0 (5)	C1—Fe2—C4—C5	38.1 (3)
C16—Si1—O1—C6	−11.6 (5)	C1ⁱ—Fe2—C4—C5	−141.9 (3)
C5—Fe2—C1—C2	118.6 (4)	C3—Fe2—C4—C5	119.6 (4)
C5ⁱ—Fe2—C1—C2	−61.4 (4)	C3ⁱ—Fe2—C4—C5	−60.4 (4)
C4—Fe2—C1—C2	81.5 (3)	C2—Fe2—C4—C5	82.0 (3)
C4ⁱ—Fe2—C1—C2	−98.5 (3)	C2ⁱ—Fe2—C4—C5	−98.0 (3)
C1ⁱ—Fe2—C1—C2	−51 (100)	C5—Fe2—C4—C3	−119.6 (4)
C3—Fe2—C1—C2	38.2 (3)	C5ⁱ—Fe2—C4—C3	60.4 (4)
C3ⁱ—Fe2—C1—C2	−141.8 (3)	C4ⁱ—Fe2—C4—C3	−102 (100)
C2ⁱ—Fe2—C1—C2	180.0	C1—Fe2—C4—C3	−81.5 (3)
C5ⁱ—Fe2—C1—C5	180.0	C1ⁱ—Fe2—C4—C3	98.5 (3)
C4—Fe2—C1—C5	−37.1 (3)	C3ⁱ—Fe2—C4—C3	180.0
C4ⁱ—Fe2—C1—C5	142.9 (3)	C2—Fe2—C4—C3	−37.6 (3)
C1ⁱ—Fe2—C1—C5	−170 (100)	C2ⁱ—Fe2—C4—C3	142.4 (3)
C3—Fe2—C1—C5	−80.3 (3)	C3—C4—C5—C1	0.0 (5)
C3ⁱ—Fe2—C1—C5	99.7 (3)	Fe2—C4—C5—C1	−59.6 (3)
C2—Fe2—C1—C5	−118.6 (4)	C3—C4—C5—Fe2	59.6 (3)
C2ⁱ—Fe2—C1—C5	61.4 (4)	C2—C1—C5—C4	0.3 (5)
C5—Fe2—C1—C6	−120.8 (5)	C6—C1—C5—C4	−175.9 (4)
C5ⁱ—Fe2—C1—C6	59.2 (5)	Fe2—C1—C5—C4	59.9 (3)
C4—Fe2—C1—C6	−157.9 (5)	C2—C1—C5—Fe2	−59.6 (3)
C4ⁱ—Fe2—C1—C6	22.1 (5)	C6—C1—C5—Fe2	124.3 (4)
C1ⁱ—Fe2—C1—C6	69 (100)	C5ⁱ—Fe2—C5—C4	−170 (100)
C3—Fe2—C1—C6	158.9 (5)	C4ⁱ—Fe2—C5—C4	180.0
C3ⁱ—Fe2—C1—C6	−21.1 (5)	C1—Fe2—C5—C4	−119.4 (4)
C2—Fe2—C1—C6	120.7 (5)	C1ⁱ—Fe2—C5—C4	60.6 (4)
C2ⁱ—Fe2—C1—C6	−59.3 (5)	C3—Fe2—C5—C4	−37.2 (3)
C5—C1—C2—C3	−0.4 (5)	C3ⁱ—Fe2—C5—C4	142.8 (3)
C6—C1—C2—C3	175.8 (4)	C2—Fe2—C5—C4	−81.4 (3)
Fe2—C1—C2—C3	−59.5 (3)	C2ⁱ—Fe2—C5—C4	98.6 (3)
C5—C1—C2—Fe2	59.1 (3)	C5ⁱ—Fe2—C5—C1	−50 (100)
C6—C1—C2—Fe2	−124.7 (4)	C4—Fe2—C5—C1	119.4 (4)
C5—Fe2—C2—C1	−38.4 (3)	C4ⁱ—Fe2—C5—C1	−60.6 (4)
C5ⁱ—Fe2—C2—C1	141.6 (3)	C1ⁱ—Fe2—C5—C1	180.0
C4—Fe2—C2—C1	−81.6 (3)	C3—Fe2—C5—C1	82.1 (3)
C4ⁱ—Fe2—C2—C1	98.4 (3)	C3ⁱ—Fe2—C5—C1	−97.9 (3)
C1ⁱ—Fe2—C2—C1	180.0	C2—Fe2—C5—C1	38.0 (3)
C3—Fe2—C2—C1	−118.5 (4)	C2ⁱ—Fe2—C5—C1	−142.0 (3)
C3ⁱ—Fe2—C2—C1	61.5 (4)	Si1—O1—C6—C7	58.0 (5)
C2ⁱ—Fe2—C2—C1	22 (100)	Si1—O1—C6—C1	174.9 (3)
C5—Fe2—C2—C3	80.1 (3)	Si1—O1—C6—C8	−64.7 (5)
C5ⁱ—Fe2—C2—C3	−99.9 (3)	C2—C1—C6—O1	30.2 (6)
C4—Fe2—C2—C3	36.9 (3)	C5—C1—C6—O1	−154.4 (4)
C4ⁱ—Fe2—C2—C3	−143.1 (3)	Fe2—C1—C6—O1	−62.5 (5)
C1—Fe2—C2—C3	118.5 (4)	C2—C1—C6—C7	148.7 (4)
C1ⁱ—Fe2—C2—C3	−61.5 (4)	C5—C1—C6—C7	−35.9 (6)
C3ⁱ—Fe2—C2—C3	180.0	Fe2—C1—C6—C7	56.0 (5)
C2ⁱ—Fe2—C2—C3	140 (100)	C2—C1—C6—C8	−92.2 (5)
C1—C2—C3—C4	0.4 (5)	C5—C1—C6—C8	83.2 (5)
Fe2—C2—C3—C4	−59.2 (3)	Fe2—C1—C6—C8	175.1 (3)
C1—C2—C3—Fe2	59.6 (3)	O1—C6—C7—N1	137 (29)
C5—Fe2—C3—C4	37.2 (3)	C1—C6—C7—N1	19 (29)
C5ⁱ—Fe2—C3—C4	−142.8 (3)	C8—C6—C7—N1	−99 (29)
C4ⁱ—Fe2—C3—C4	180.0	O1—C6—C8—C13	131.0 (5)
C1—Fe2—C3—C4	81.8 (3)	C7—C6—C8—C13	8.5 (6)
C1ⁱ—Fe2—C3—C4	−98.2 (3)	C1—C6—C8—C13	−109.0 (5)
C3ⁱ—Fe2—C3—C4	127 (100)	O1—C6—C8—C9	−50.2 (6)
C2—Fe2—C3—C4	119.9 (4)	C7—C6—C8—C9	−172.7 (4)
C2ⁱ—Fe2—C3—C4	−60.1 (4)	C1—C6—C8—C9	69.9 (5)
C5—Fe2—C3—C2	−82.7 (3)	C13—C8—C9—C10	−1.2 (7)
C5ⁱ—Fe2—C3—C2	97.3 (3)	C6—C8—C9—C10	179.9 (4)
C4—Fe2—C3—C2	−119.9 (4)	C8—C9—C10—C11	0.1 (8)
C4ⁱ—Fe2—C3—C2	60.1 (4)	C14—O2—C11—C12	−1.0 (8)
C1—Fe2—C3—C2	−38.1 (3)	C14—O2—C11—C10	178.6 (5)
C1ⁱ—Fe2—C3—C2	141.9 (3)	C9—C10—C11—O2	−177.9 (5)
C3ⁱ—Fe2—C3—C2	7 (100)	C9—C10—C11—C12	1.8 (7)
C2ⁱ—Fe2—C3—C2	180.0	O2—C11—C12—C13	177.2 (5)
C2—C3—C4—C5	−0.2 (5)	C10—C11—C12—C13	−2.4 (8)
Fe2—C3—C4—C5	−59.3 (3)	C9—C8—C13—C12	0.5 (7)
C2—C3—C4—Fe2	59.1 (3)	C6—C8—C13—C12	179.4 (4)
C5ⁱ—Fe2—C4—C5	180.0	C11—C12—C13—C8	1.3 (8)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₇H₂₀NO₂Si)₂]
M_r	652.71
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.129 (2), 10.500 (4), 11.449 (4)
α, β, γ (°)	95.613 (5), 97.253 (6), 97.441 (6)
V (Å³)	837.3 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.24 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.822, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4803, 3367, 2156
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.204, 1.03
No. of reflections	3367
No. of parameters	196
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.43

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20062004) for financial support.

References

Bruker (1999) SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dunitz, J. D., Orgel, L. E. & Rich, A. (1956). Acta Cryst. 9, 373–375. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Evans, D. A., Carroll, G. L. & Truesdale, L. K. (1974). J. Org. Chem. 39, 914–917. CrossRef CAS Web of Science Google Scholar
Evans, D. A. & Truesdale, L. K. (1973). Tetrahedron Lett. 49, 4929–4932. CrossRef Google Scholar
Fischer, K. & Hüning, S. (1987). J. Org. Chem. 52, 564–569. CrossRef CAS Web of Science Google Scholar
Fleming, L. & Woolias, M. (1979). J. Chem. Soc. Perkin Trans. 1, pp. 829–837. CrossRef Web of Science Google Scholar
Gassman, P. G. & Talley, J. J. (1978). Tetrahedron Lett. 40, 3773–3776. CrossRef Google Scholar
Groutas, W. C. & Felker, D. (1980). Synthesis, pp. 861–868. CrossRef Google Scholar
Lidy, W. & Sundermeyer, W. (1973). Chem. Ber. 106, 587–593. CrossRef CAS Web of Science Google Scholar
Rasmussen, J. K. & Heilmann, S. M. (1978). Synthesis, pp. 219–221. CrossRef Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Zhou, G. D. (1989). Foundations of Structural Chemistry, 1st ed., p. 230. Beijing University Press. Google Scholar

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