[(N,N-Dimethyl­amino)methyl­ferrocen­yl]meth­yl(N-methyl­anilino)phenyl­silane

The title compound, [Fe(C₅H₅)(C₂₂H₂₇N₂Si)], is a diasteromeric N,N-dimethyl­amino­methyl­ferrocenylsilane having chirality at the ferrocenyl unit and at the Si atom. The compound crystallizes in a centrosymmetric space group containing two out of the possible four isomers.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.030
• wR factor = 0.087
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

[(N,N-Dimethylamino)methylferrocenyl]methyl(N-methylanilino)phenylsilane

Crystal data

[Fe(C5H5)(C22H27N2Si)]	F(000) = 992
Mr = 468.49	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Melting point: 376 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.5905 (11) Å	Cell parameters from 9777 reflections
b = 8.6684 (6) Å	θ = 3.3–21.6°
c = 21.2931 (11) Å	µ = 0.71 mm^−1
β = 125.320 (4)°	T = 93 K
V = 2348.0 (3) Å^3	Prism, orange
Z = 4	0.33 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5389 independent reflections
Radiation source: sealed tube	4601 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −20→20
Tmin = 0.800, Tmax = 0.907	k = −11→11
47177 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.9734P] where P = (Fo^2 + 2Fc^2)/3
5389 reflections	(Δ/σ)max = 0.001
285 parameters	Δρmax = 0.95 e Å^−3
0 restraints	Δρmin = −0.66 e Å^−3

Special details

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. The hydrogen atoms at the methyl group C14 are rotational disordered.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.327847 (16)	0.20044 (2)	0.600816 (11)	0.01141 (7)
Si1	0.31352 (3)	0.50729 (4)	0.48605 (2)	0.01076 (9)
N1	0.06651 (10)	0.26283 (16)	0.35522 (7)	0.0167 (3)
N2	0.29663 (10)	0.52218 (14)	0.39727 (7)	0.0133 (2)
C1	0.31145 (12)	0.29930 (16)	0.50597 (8)	0.0120 (3)
C2	0.22440 (12)	0.19794 (16)	0.48325 (8)	0.0129 (3)
C3	0.26540 (12)	0.04693 (17)	0.51185 (8)	0.0154 (3)
H3	0.2240	−0.0446	0.5051	0.019*
C4	0.37664 (12)	0.05241 (17)	0.55290 (9)	0.0162 (3)
H4	0.4250	−0.0346	0.5788	0.019*
C5	0.40513 (12)	0.20619 (16)	0.54930 (8)	0.0135 (3)
H5	0.4771	0.2433	0.5733	0.016*
C6	0.26296 (13)	0.31078 (18)	0.64916 (9)	0.0179 (3)
H6	0.2021	0.3753	0.6236	0.021*
C7	0.26443 (13)	0.1487 (2)	0.65985 (9)	0.0194 (3)
H7	0.2046	0.0848	0.6419	0.023*
C8	0.37066 (13)	0.09757 (19)	0.70141 (9)	0.0191 (3)
H8	0.3943	−0.0064	0.7159	0.023*
C9	0.43529 (13)	0.22828 (19)	0.71712 (9)	0.0182 (3)
H9	0.5100	0.2279	0.7446	0.022*
C10	0.36874 (13)	0.36007 (18)	0.68467 (9)	0.0180 (3)
H10	0.3910	0.4635	0.6862	0.022*
C11	0.11011 (12)	0.23833 (18)	0.43664 (8)	0.0152 (3)
H11A	0.0709	0.1541	0.4410	0.018*
H11B	0.1005	0.3333	0.4578	0.018*
C12	0.07056 (13)	0.1216 (2)	0.32002 (9)	0.0228 (3)
H12A	0.0255	0.0434	0.3204	0.034*
H12B	0.1431	0.0838	0.3492	0.034*
H12C	0.0458	0.1427	0.2668	0.034*
C13	−0.04237 (13)	0.3136 (2)	0.31461 (10)	0.0243 (4)
H13A	−0.0714	0.3316	0.2603	0.036*
H13B	−0.0452	0.4095	0.3377	0.036*
H13C	−0.0837	0.2339	0.3185	0.036*
C14	0.44421 (12)	0.58640 (18)	0.56516 (9)	0.0164 (3)
H14A	0.4814	0.5101	0.6066	0.020*	0.51 (2)
H14B	0.4340	0.6811	0.5852	0.020*	0.51 (2)
H14C	0.4858	0.6095	0.5452	0.020*	0.51 (2)
H14D	0.4546	0.6877	0.5500	0.020*	0.49 (2)
H14E	0.4999	0.5160	0.5749	0.020*	0.49 (2)
H14F	0.4467	0.5970	0.6120	0.020*	0.49 (2)
C15	0.20442 (11)	0.61535 (16)	0.48000 (8)	0.0129 (3)
C16	0.11261 (12)	0.65346 (19)	0.40862 (9)	0.0180 (3)
H16	0.1068	0.6277	0.3629	0.022*
C17	0.02948 (13)	0.7283 (2)	0.40305 (10)	0.0227 (3)
H17	−0.0320	0.7537	0.3539	0.027*
C18	0.03626 (13)	0.7658 (2)	0.46901 (10)	0.0226 (3)
H18	−0.0208	0.8157	0.4652	0.027*
C19	0.12681 (14)	0.73007 (19)	0.54065 (10)	0.0212 (3)
H19	0.1320	0.7556	0.5861	0.025*
C20	0.20997 (13)	0.65674 (17)	0.54564 (9)	0.0167 (3)
H20	0.2721	0.6343	0.5950	0.020*
C21	0.26796 (12)	0.38739 (17)	0.34725 (9)	0.0164 (3)
H21A	0.2021	0.4082	0.2970	0.025*
H21B	0.2587	0.2977	0.3708	0.025*
H21C	0.3239	0.3661	0.3405	0.025*
C22	0.30766 (11)	0.66184 (17)	0.36919 (8)	0.0126 (3)
C23	0.30472 (12)	0.66837 (18)	0.30196 (8)	0.0149 (3)
H23	0.2955	0.5763	0.2745	0.018*
C24	0.31527 (12)	0.80856 (19)	0.27545 (9)	0.0175 (3)
H24	0.3123	0.8105	0.2296	0.021*
C25	0.32997 (12)	0.94567 (19)	0.31393 (9)	0.0184 (3)
H25	0.3374	1.0407	0.2953	0.022*
C26	0.33354 (13)	0.93988 (18)	0.38067 (9)	0.0180 (3)
H26	0.3445	1.0322	0.4084	0.022*
C27	0.32145 (12)	0.80192 (17)	0.40731 (9)	0.0156 (3)
H27	0.3225	0.8017	0.4524	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01308 (12)	0.01327 (12)	0.00688 (12)	0.00082 (7)	0.00520 (9)	0.00098 (7)
Si1	0.01195 (19)	0.01277 (18)	0.00703 (18)	0.00057 (14)	0.00519 (16)	0.00039 (14)
N1	0.0129 (6)	0.0237 (6)	0.0090 (6)	0.0001 (5)	0.0037 (5)	0.0010 (5)
N2	0.0165 (6)	0.0144 (6)	0.0102 (6)	−0.0009 (5)	0.0084 (5)	−0.0010 (5)
C1	0.0140 (7)	0.0151 (7)	0.0059 (6)	0.0005 (5)	0.0053 (6)	−0.0002 (5)
C2	0.0148 (7)	0.0153 (7)	0.0076 (7)	−0.0013 (5)	0.0060 (6)	−0.0016 (5)
C3	0.0205 (8)	0.0148 (7)	0.0113 (7)	−0.0017 (6)	0.0093 (6)	−0.0018 (5)
C4	0.0208 (8)	0.0152 (7)	0.0118 (7)	0.0030 (6)	0.0090 (6)	−0.0004 (5)
C5	0.0143 (7)	0.0162 (7)	0.0098 (7)	0.0013 (5)	0.0070 (6)	−0.0005 (5)
C6	0.0201 (8)	0.0248 (8)	0.0107 (7)	0.0044 (6)	0.0101 (6)	0.0012 (6)
C7	0.0207 (8)	0.0273 (8)	0.0137 (7)	−0.0004 (6)	0.0119 (7)	0.0035 (6)
C8	0.0232 (8)	0.0213 (8)	0.0117 (7)	0.0035 (6)	0.0096 (7)	0.0061 (6)
C9	0.0166 (8)	0.0265 (8)	0.0076 (7)	0.0017 (6)	0.0047 (6)	0.0005 (6)
C10	0.0224 (8)	0.0202 (7)	0.0107 (7)	0.0001 (6)	0.0092 (6)	−0.0017 (6)
C11	0.0143 (7)	0.0205 (7)	0.0093 (7)	−0.0024 (6)	0.0060 (6)	−0.0006 (6)
C12	0.0221 (8)	0.0299 (9)	0.0118 (7)	−0.0039 (7)	0.0072 (7)	−0.0052 (6)
C13	0.0147 (8)	0.0331 (9)	0.0165 (8)	0.0021 (7)	0.0041 (7)	0.0029 (7)
C14	0.0159 (7)	0.0182 (7)	0.0121 (7)	−0.0013 (6)	0.0064 (6)	−0.0013 (6)
C15	0.0153 (7)	0.0126 (6)	0.0121 (7)	−0.0001 (5)	0.0088 (6)	0.0013 (5)
C16	0.0172 (8)	0.0230 (8)	0.0126 (7)	0.0021 (6)	0.0080 (6)	0.0004 (6)
C17	0.0167 (8)	0.0284 (8)	0.0191 (8)	0.0053 (6)	0.0081 (7)	0.0028 (7)
C18	0.0210 (8)	0.0250 (8)	0.0280 (9)	0.0053 (6)	0.0178 (8)	0.0033 (7)
C19	0.0281 (9)	0.0233 (8)	0.0202 (8)	0.0044 (7)	0.0185 (8)	0.0024 (6)
C20	0.0201 (8)	0.0171 (7)	0.0133 (7)	0.0036 (6)	0.0100 (6)	0.0030 (6)
C21	0.0205 (8)	0.0179 (7)	0.0112 (7)	−0.0021 (6)	0.0094 (6)	−0.0028 (6)
C22	0.0110 (7)	0.0167 (7)	0.0091 (7)	0.0020 (5)	0.0053 (6)	0.0024 (5)
C23	0.0133 (7)	0.0216 (7)	0.0092 (7)	0.0008 (6)	0.0062 (6)	0.0000 (6)
C24	0.0145 (7)	0.0288 (8)	0.0092 (7)	0.0004 (6)	0.0068 (6)	0.0037 (6)
C25	0.0186 (8)	0.0207 (7)	0.0167 (7)	0.0023 (6)	0.0106 (6)	0.0068 (6)
C26	0.0218 (8)	0.0164 (7)	0.0187 (8)	0.0024 (6)	0.0134 (7)	0.0026 (6)
C27	0.0190 (8)	0.0179 (7)	0.0130 (7)	0.0020 (6)	0.0111 (6)	0.0015 (5)

Geometric parameters (Å, º)

Fe1—C4	2.0404 (15)	C11—H11B	0.9900
Fe1—C3	2.0432 (15)	C12—H12A	0.9800
Fe1—C8	2.0434 (15)	C12—H12B	0.9800
Fe1—C5	2.0458 (15)	C12—H12C	0.9800
Fe1—C10	2.0477 (15)	C13—H13A	0.9800
Fe1—C7	2.0484 (15)	C13—H13B	0.9800
Fe1—C2	2.0494 (15)	C13—H13C	0.9800
Fe1—C9	2.0495 (16)	C14—H14A	0.9800
Fe1—C6	2.0500 (15)	C14—H14B	0.9800
Fe1—C1	2.0692 (14)	C14—H14C	0.9800
Si1—N2	1.756 (1)	C14—H14D	0.9800
Si1—C1	1.857 (2)	C14—H14E	0.9800
Si1—C14	1.868 (2)	C14—H14F	0.9800
Si1—C15	1.880 (2)	C15—C20	1.396 (2)
N1—C12	1.455 (2)	C15—C16	1.397 (2)
N1—C13	1.458 (2)	C16—C17	1.392 (2)
N1—C11	1.4665 (19)	C16—H16	0.9500
N2—C22	1.4041 (18)	C17—C18	1.385 (2)
N2—C21	1.4659 (18)	C17—H17	0.9500
C1—C5	1.441 (2)	C18—C19	1.388 (2)
C1—C2	1.445 (2)	C18—H18	0.9500
C2—C3	1.429 (2)	C19—C20	1.392 (2)
C2—C11	1.496 (2)	C19—H19	0.9500
C3—C4	1.422 (2)	C20—H20	0.9500
C3—H3	0.9800	C21—H21A	0.9800
C4—C5	1.421 (2)	C21—H21B	0.9800
C4—H4	0.9800	C21—H21C	0.9800
C5—H5	0.9800	C22—C27	1.406 (2)
C6—C7	1.421 (2)	C22—C23	1.407 (2)
C6—C10	1.426 (2)	C23—C24	1.389 (2)
C6—H6	0.9551	C23—H23	0.9500
C7—C8	1.424 (2)	C24—C25	1.385 (2)
C7—H7	0.9549	C24—H24	0.9500
C8—C9	1.422 (2)	C25—C26	1.391 (2)
C8—H8	0.9550	C25—H25	0.9500
C9—C10	1.425 (2)	C26—C27	1.383 (2)
C9—H9	0.9549	C26—H26	0.9500
C10—H10	0.9549	C27—H27	0.9500
C11—H11A	0.9900
C4—Fe1—C3	40.75 (6)	C6—C7—C8	108.21 (14)
C4—Fe1—C8	105.03 (6)	C6—C7—Fe1	69.77 (9)
C3—Fe1—C8	112.30 (6)	C8—C7—Fe1	69.45 (9)
C4—Fe1—C5	40.70 (6)	C6—C7—H7	126.0
C3—Fe1—C5	68.37 (6)	C8—C7—H7	125.8
C8—Fe1—C5	129.49 (6)	Fe1—C7—H7	126.1
C4—Fe1—C10	147.44 (6)	C9—C8—C7	108.04 (14)
C3—Fe1—C10	171.81 (6)	C9—C8—Fe1	69.90 (9)
C8—Fe1—C10	68.44 (6)	C7—C8—Fe1	69.82 (9)
C5—Fe1—C10	117.91 (6)	C9—C8—H8	126.0
C4—Fe1—C7	128.38 (7)	C7—C8—H8	125.9
C3—Fe1—C7	106.62 (7)	Fe1—C8—H8	125.6
C8—Fe1—C7	40.73 (6)	C8—C9—C10	107.85 (14)
C5—Fe1—C7	167.73 (6)	C8—C9—Fe1	69.44 (9)
C10—Fe1—C7	68.31 (7)	C10—C9—Fe1	69.58 (9)
C4—Fe1—C2	68.91 (6)	C8—C9—H9	126.1
C3—Fe1—C2	40.88 (6)	C10—C9—H9	126.1
C8—Fe1—C2	145.62 (6)	Fe1—C9—H9	126.6
C5—Fe1—C2	68.70 (6)	C9—C10—C6	108.16 (14)
C10—Fe1—C2	134.48 (6)	C9—C10—Fe1	69.72 (9)
C7—Fe1—C2	115.41 (6)	C6—C10—Fe1	69.73 (9)
C4—Fe1—C9	113.43 (6)	C9—C10—H10	126.0
C3—Fe1—C9	144.63 (6)	C6—C10—H10	125.8
C8—Fe1—C9	40.65 (6)	Fe1—C10—H10	126.0
C5—Fe1—C9	108.76 (6)	N1—C11—C2	112.23 (12)
C10—Fe1—C9	40.70 (6)	N1—C11—H11A	109.2
C7—Fe1—C9	68.38 (7)	C2—C11—H11A	109.2
C2—Fe1—C9	173.45 (6)	N1—C11—H11B	109.2
C4—Fe1—C6	168.35 (6)	C2—C11—H11B	109.2
C3—Fe1—C6	131.34 (7)	H11A—C11—H11B	107.9
C8—Fe1—C6	68.54 (6)	N1—C12—H12A	109.5
C5—Fe1—C6	150.75 (6)	N1—C12—H12B	109.5
C10—Fe1—C6	40.72 (6)	H12A—C12—H12B	109.5
C7—Fe1—C6	40.59 (6)	N1—C12—H12C	109.5
C2—Fe1—C6	110.49 (6)	H12A—C12—H12C	109.5
C9—Fe1—C6	68.54 (6)	H12B—C12—H12C	109.5
C4—Fe1—C1	69.14 (6)	N1—C13—H13A	109.5
C3—Fe1—C1	68.97 (6)	N1—C13—H13B	109.5
C8—Fe1—C1	170.06 (6)	H13A—C13—H13B	109.5
C5—Fe1—C1	41.00 (6)	N1—C13—H13C	109.5
C10—Fe1—C1	111.82 (6)	H13A—C13—H13C	109.5
C7—Fe1—C1	149.16 (6)	H13B—C13—H13C	109.5
C2—Fe1—C1	41.08 (6)	Si1—C14—H14A	109.5
C9—Fe1—C1	133.16 (6)	Si1—C14—H14B	109.5
C6—Fe1—C1	118.59 (6)	Si1—C14—H14C	109.5
N2—Si1—C1	107.80 (6)	Si1—C14—H14D	109.5
N2—Si1—C14	110.50 (7)	Si1—C14—H14E	109.5
C1—Si1—C14	107.72 (7)	H14D—C14—H14E	109.5
N2—Si1—C15	108.84 (6)	Si1—C14—H14F	109.5
C1—Si1—C15	111.41 (6)	H14D—C14—H14F	109.5
C14—Si1—C15	110.54 (7)	H14E—C14—H14F	109.5
C12—N1—C13	109.32 (13)	C20—C15—C16	117.37 (14)
C12—N1—C11	111.01 (13)	C20—C15—Si1	121.97 (11)
C13—N1—C11	109.26 (13)	C16—C15—Si1	120.63 (11)
C22—N2—C21	116.03 (12)	C17—C16—C15	121.37 (15)
C22—N2—Si1	122.87 (10)	C17—C16—H16	119.3
C21—N2—Si1	121.10 (10)	C15—C16—H16	119.3
C5—C1—C2	106.36 (12)	C18—C17—C16	120.11 (16)
C5—C1—Si1	123.03 (11)	C18—C17—H17	119.9
C2—C1—Si1	130.60 (11)	C16—C17—H17	119.9
C5—C1—Fe1	68.63 (8)	C17—C18—C19	119.68 (15)
C2—C1—Fe1	68.73 (8)	C17—C18—H18	120.2
Si1—C1—Fe1	128.06 (7)	C19—C18—H18	120.2
C3—C2—C1	108.19 (13)	C18—C19—C20	119.78 (15)
C3—C2—C11	124.38 (13)	C18—C19—H19	120.1
C1—C2—C11	127.42 (13)	C20—C19—H19	120.1
C3—C2—Fe1	69.32 (8)	C19—C20—C15	121.67 (15)
C1—C2—Fe1	70.19 (8)	C19—C20—H20	119.2
C11—C2—Fe1	127.03 (10)	C15—C20—H20	119.2
C4—C3—C2	108.50 (13)	N2—C21—H21A	109.5
C4—C3—Fe1	69.52 (8)	N2—C21—H21B	109.5
C2—C3—Fe1	69.79 (8)	H21A—C21—H21B	109.5
C4—C3—H3	125.7	N2—C21—H21C	109.5
C2—C3—H3	125.8	H21A—C21—H21C	109.5
Fe1—C3—H3	125.7	H21B—C21—H21C	109.5
C5—C4—C3	107.84 (13)	N2—C22—C27	120.94 (13)
C5—C4—Fe1	69.85 (8)	N2—C22—C23	121.88 (13)
C3—C4—Fe1	69.73 (8)	C27—C22—C23	117.18 (14)
C5—C4—H4	126.1	C24—C23—C22	120.46 (14)
C3—C4—H4	126.0	C24—C23—H23	119.8
Fe1—C4—H4	126.1	C22—C23—H23	119.8
C4—C5—C1	109.10 (13)	C25—C24—C23	121.88 (14)
C4—C5—Fe1	69.45 (8)	C25—C24—H24	119.1
C1—C5—Fe1	70.37 (8)	C23—C24—H24	119.1
C4—C5—H5	125.4	C24—C25—C26	117.95 (14)
C1—C5—H5	125.5	C24—C25—H25	121.0
Fe1—C5—H5	125.5	C26—C25—H25	121.0
C7—C6—C10	107.74 (14)	C27—C26—C25	121.08 (15)
C7—C6—Fe1	69.65 (9)	C27—C26—H26	119.5
C10—C6—Fe1	69.55 (9)	C25—C26—H26	119.5
C7—C6—H6	126.1	C26—C27—C22	121.44 (14)
C10—C6—H6	126.2	C26—C27—H27	119.3
Fe1—C6—H6	127.1	C22—C27—H27	119.3
C1—Si1—N2—C22	−171.62 (11)	C7—Fe1—C5—C1	150.3 (3)
C14—Si1—N2—C22	−54.15 (13)	C2—Fe1—C5—C1	38.31 (8)
C15—Si1—N2—C22	67.40 (13)	C9—Fe1—C5—C1	−135.26 (9)
C1—Si1—N2—C21	9.49 (13)	C6—Fe1—C5—C1	−55.87 (16)
C14—Si1—N2—C21	126.96 (12)	C4—Fe1—C6—C7	20.7 (4)
C15—Si1—N2—C21	−111.48 (12)	C3—Fe1—C6—C7	63.81 (12)
N2—Si1—C1—C5	92.12 (13)	C8—Fe1—C6—C7	−37.56 (10)
C14—Si1—C1—C5	−27.13 (14)	C5—Fe1—C6—C7	−171.71 (12)
C15—Si1—C1—C5	−148.52 (12)	C10—Fe1—C6—C7	−119.02 (13)
N2—Si1—C1—C2	−86.67 (14)	C2—Fe1—C6—C7	105.54 (10)
C14—Si1—C1—C2	154.07 (13)	C9—Fe1—C6—C7	−81.39 (10)
C15—Si1—C1—C2	32.68 (16)	C1—Fe1—C6—C7	150.08 (9)
N2—Si1—C1—Fe1	179.65 (8)	C4—Fe1—C6—C10	139.7 (3)
C14—Si1—C1—Fe1	60.39 (11)	C3—Fe1—C6—C10	−177.17 (9)
C15—Si1—C1—Fe1	−61.00 (11)	C8—Fe1—C6—C10	81.46 (10)
C4—Fe1—C1—C5	−37.05 (9)	C5—Fe1—C6—C10	−52.69 (16)
C3—Fe1—C1—C5	−80.82 (9)	C7—Fe1—C6—C10	119.02 (13)
C10—Fe1—C1—C5	107.93 (9)	C2—Fe1—C6—C10	−135.44 (9)
C7—Fe1—C1—C5	−168.16 (11)	C9—Fe1—C6—C10	37.62 (9)
C2—Fe1—C1—C5	−118.49 (12)	C1—Fe1—C6—C10	−90.90 (10)
C9—Fe1—C1—C5	66.01 (11)	C10—C6—C7—C8	−0.35 (17)
C6—Fe1—C1—C5	152.57 (9)	Fe1—C6—C7—C8	58.99 (11)
C4—Fe1—C1—C2	81.44 (9)	C10—C6—C7—Fe1	−59.35 (11)
C3—Fe1—C1—C2	37.67 (8)	C4—Fe1—C7—C6	−174.77 (9)
C5—Fe1—C1—C2	118.49 (12)	C3—Fe1—C7—C6	−135.32 (10)
C10—Fe1—C1—C2	−133.58 (9)	C8—Fe1—C7—C6	119.59 (14)
C7—Fe1—C1—C2	−49.67 (15)	C5—Fe1—C7—C6	160.6 (3)
C9—Fe1—C1—C2	−175.50 (9)	C10—Fe1—C7—C6	37.88 (9)
C6—Fe1—C1—C2	−88.94 (10)	C2—Fe1—C7—C6	−92.36 (10)
C4—Fe1—C1—Si1	−152.95 (11)	C9—Fe1—C7—C6	81.82 (10)
C3—Fe1—C1—Si1	163.27 (12)	C1—Fe1—C7—C6	−58.67 (16)
C5—Fe1—C1—Si1	−115.91 (13)	C4—Fe1—C7—C8	65.63 (12)
C10—Fe1—C1—Si1	−7.97 (12)	C3—Fe1—C7—C8	105.08 (10)
C7—Fe1—C1—Si1	75.93 (16)	C5—Fe1—C7—C8	41.0 (3)
C2—Fe1—C1—Si1	125.60 (14)	C10—Fe1—C7—C8	−81.72 (10)
C9—Fe1—C1—Si1	−49.89 (13)	C2—Fe1—C7—C8	148.05 (9)
C6—Fe1—C1—Si1	36.66 (12)	C9—Fe1—C7—C8	−37.77 (10)
C5—C1—C2—C3	−0.57 (16)	C6—Fe1—C7—C8	−119.59 (14)
Si1—C1—C2—C3	178.37 (11)	C1—Fe1—C7—C8	−178.26 (11)
Fe1—C1—C2—C3	−59.11 (10)	C6—C7—C8—C9	0.50 (18)
C5—C1—C2—C11	−179.43 (14)	Fe1—C7—C8—C9	59.69 (11)
Si1—C1—C2—C11	−0.5 (2)	C6—C7—C8—Fe1	−59.19 (11)
Fe1—C1—C2—C11	122.03 (15)	C4—Fe1—C8—C9	108.62 (10)
C5—C1—C2—Fe1	58.54 (10)	C3—Fe1—C8—C9	151.08 (9)
Si1—C1—C2—Fe1	−122.52 (12)	C5—Fe1—C8—C9	71.35 (12)
C4—Fe1—C2—C3	37.34 (9)	C10—Fe1—C8—C9	−37.71 (9)
C8—Fe1—C2—C3	−48.57 (15)	C7—Fe1—C8—C9	−119.07 (14)
C5—Fe1—C2—C3	81.14 (9)	C2—Fe1—C8—C9	−176.88 (10)
C10—Fe1—C2—C3	−170.12 (9)	C6—Fe1—C8—C9	−81.63 (10)
C7—Fe1—C2—C3	−86.27 (10)	C4—Fe1—C8—C7	−132.32 (10)
C6—Fe1—C2—C3	−130.21 (9)	C3—Fe1—C8—C7	−89.85 (11)
C1—Fe1—C2—C3	119.38 (12)	C5—Fe1—C8—C7	−169.58 (9)
C4—Fe1—C2—C1	−82.04 (9)	C10—Fe1—C8—C7	81.36 (10)
C3—Fe1—C2—C1	−119.38 (12)	C2—Fe1—C8—C7	−57.82 (15)
C8—Fe1—C2—C1	−167.95 (10)	C9—Fe1—C8—C7	119.07 (14)
C5—Fe1—C2—C1	−38.24 (8)	C6—Fe1—C8—C7	37.44 (10)
C10—Fe1—C2—C1	70.50 (11)	C7—C8—C9—C10	−0.45 (17)
C7—Fe1—C2—C1	154.36 (9)	Fe1—C8—C9—C10	59.19 (11)
C6—Fe1—C2—C1	110.41 (9)	C7—C8—C9—Fe1	−59.64 (11)
C4—Fe1—C2—C11	155.46 (14)	C4—Fe1—C9—C8	−85.94 (10)
C3—Fe1—C2—C11	118.12 (16)	C3—Fe1—C9—C8	−50.62 (15)
C8—Fe1—C2—C11	69.55 (17)	C5—Fe1—C9—C8	−129.44 (9)
C5—Fe1—C2—C11	−160.74 (14)	C10—Fe1—C9—C8	119.27 (13)
C10—Fe1—C2—C11	−52.00 (16)	C7—Fe1—C9—C8	37.84 (9)
C7—Fe1—C2—C11	31.85 (15)	C6—Fe1—C9—C8	81.63 (10)
C6—Fe1—C2—C11	−12.09 (14)	C1—Fe1—C9—C8	−168.72 (9)
C1—Fe1—C2—C11	−122.50 (16)	C4—Fe1—C9—C10	154.79 (9)
C1—C2—C3—C4	0.74 (16)	C3—Fe1—C9—C10	−169.89 (10)
C11—C2—C3—C4	179.64 (13)	C8—Fe1—C9—C10	−119.27 (13)
Fe1—C2—C3—C4	−58.92 (10)	C5—Fe1—C9—C10	111.29 (10)
C1—C2—C3—Fe1	59.65 (10)	C7—Fe1—C9—C10	−81.43 (10)
C11—C2—C3—Fe1	−121.44 (14)	C6—Fe1—C9—C10	−37.64 (9)
C8—Fe1—C3—C4	−87.34 (10)	C1—Fe1—C9—C10	72.01 (12)
C5—Fe1—C3—C4	37.89 (9)	C8—C9—C10—C6	0.23 (17)
C7—Fe1—C3—C4	−130.26 (9)	Fe1—C9—C10—C6	59.33 (10)
C2—Fe1—C3—C4	119.90 (12)	C8—C9—C10—Fe1	−59.10 (11)
C9—Fe1—C3—C4	−54.37 (14)	C7—C6—C10—C9	0.08 (17)
C6—Fe1—C3—C4	−167.79 (9)	Fe1—C6—C10—C9	−59.33 (10)
C1—Fe1—C3—C4	82.05 (9)	C7—C6—C10—Fe1	59.40 (11)
C4—Fe1—C3—C2	−119.90 (12)	C4—Fe1—C10—C9	−46.57 (16)
C8—Fe1—C3—C2	152.76 (9)	C8—Fe1—C10—C9	37.67 (9)
C5—Fe1—C3—C2	−82.01 (9)	C5—Fe1—C10—C9	−86.70 (10)
C7—Fe1—C3—C2	109.85 (9)	C7—Fe1—C10—C9	81.64 (10)
C9—Fe1—C3—C2	−174.26 (10)	C2—Fe1—C10—C9	−173.49 (9)
C6—Fe1—C3—C2	72.31 (11)	C6—Fe1—C10—C9	119.39 (13)
C1—Fe1—C3—C2	−37.84 (9)	C1—Fe1—C10—C9	−131.64 (9)
C2—C3—C4—C5	−0.61 (17)	C4—Fe1—C10—C6	−165.96 (11)
Fe1—C3—C4—C5	−59.69 (10)	C8—Fe1—C10—C6	−81.73 (10)
C2—C3—C4—Fe1	59.08 (10)	C5—Fe1—C10—C6	153.91 (9)
C3—Fe1—C4—C5	118.91 (13)	C7—Fe1—C10—C6	−37.76 (9)
C8—Fe1—C4—C5	−134.23 (9)	C2—Fe1—C10—C6	67.11 (12)
C10—Fe1—C4—C5	−60.86 (15)	C9—Fe1—C10—C6	−119.39 (13)
C7—Fe1—C4—C5	−172.21 (9)	C1—Fe1—C10—C6	108.97 (10)
C2—Fe1—C4—C5	81.45 (9)	C12—N1—C11—C2	63.87 (16)
C9—Fe1—C4—C5	−91.93 (10)	C13—N1—C11—C2	−175.49 (13)
C6—Fe1—C4—C5	170.7 (3)	C3—C2—C11—N1	−105.98 (16)
C1—Fe1—C4—C5	37.31 (9)	C1—C2—C11—N1	72.71 (19)
C8—Fe1—C4—C3	106.86 (9)	Fe1—C2—C11—N1	165.16 (10)
C5—Fe1—C4—C3	−118.91 (13)	N2—Si1—C15—C20	−163.93 (12)
C10—Fe1—C4—C3	−179.77 (11)	C1—Si1—C15—C20	77.34 (14)
C7—Fe1—C4—C3	68.88 (11)	C14—Si1—C15—C20	−42.40 (14)
C2—Fe1—C4—C3	−37.46 (9)	N2—Si1—C15—C16	17.95 (14)
C9—Fe1—C4—C3	149.15 (9)	C1—Si1—C15—C16	−100.78 (13)
C6—Fe1—C4—C3	51.8 (3)	C14—Si1—C15—C16	139.48 (12)
C1—Fe1—C4—C3	−81.60 (9)	C20—C15—C16—C17	−0.6 (2)
C3—C4—C5—C1	0.25 (17)	Si1—C15—C16—C17	177.57 (13)
Fe1—C4—C5—C1	−59.37 (10)	C15—C16—C17—C18	−0.4 (3)
C3—C4—C5—Fe1	59.62 (10)	C16—C17—C18—C19	0.8 (3)
C2—C1—C5—C4	0.20 (16)	C17—C18—C19—C20	−0.1 (3)
Si1—C1—C5—C4	−178.84 (10)	C18—C19—C20—C15	−1.0 (2)
Fe1—C1—C5—C4	58.80 (10)	C16—C15—C20—C19	1.4 (2)
C2—C1—C5—Fe1	−58.60 (10)	Si1—C15—C20—C19	−176.81 (12)
Si1—C1—C5—Fe1	122.35 (11)	C21—N2—C22—C27	171.68 (13)
C3—Fe1—C5—C4	−37.93 (9)	Si1—N2—C22—C27	−7.3 (2)
C8—Fe1—C5—C4	63.74 (12)	C21—N2—C22—C23	−7.9 (2)
C10—Fe1—C5—C4	147.86 (9)	Si1—N2—C22—C23	173.19 (11)
C7—Fe1—C5—C4	30.0 (3)	N2—C22—C23—C24	179.63 (14)
C2—Fe1—C5—C4	−82.01 (9)	C27—C22—C23—C24	0.1 (2)
C9—Fe1—C5—C4	104.42 (10)	C22—C23—C24—C25	0.7 (2)
C6—Fe1—C5—C4	−176.18 (12)	C23—C24—C25—C26	−0.3 (2)
C1—Fe1—C5—C4	−120.32 (12)	C24—C25—C26—C27	−0.8 (2)
C4—Fe1—C5—C1	120.32 (12)	C25—C26—C27—C22	1.6 (2)
C3—Fe1—C5—C1	82.39 (9)	N2—C22—C27—C26	179.28 (14)
C8—Fe1—C5—C1	−175.95 (9)	C23—C22—C27—C26	−1.2 (2)
C10—Fe1—C5—C1	−91.82 (10)