Chloridobis{N-[(dimethyl-amino)dimethyl-silyl]-2,6-dimethyl-anilido-κN,N'}iron(III).

The title iron(III) compound, [Fe(C(12)H(21)N(2)Si)(2)Cl], is monomeric. The Fe atom is N,N'-chelated by the N-silylated anilide ligand. The two ligands around the Fe atom are arranged trans to each other. The Fe-N(amino) bond is longer than the Fe-N(anilide) bond by about 0.37 Å. The mol-ecule displays a pseudo-twofold rotation. The five-coordinate Fe atom demonstrates a highly distorted trigonal-bipyramidal geometry.

Related literature

For related chelate iron(III) compounds and their applications, involving, for example, porphyrin, bypyridine, n class="Chemical">amidinate as well as guanidinate, see: Rath et al. (2004 ▶); Schunemann et al. (1999 ▶); Collomb et al. (1999 ▶); O’Keefe et al. (2002 ▶); Foley et al. (2000 ▶). For related zinc compounds with analogous analido ligands, see: Schumann et al. (2000 ▶).

Experimental

Crystal data

[Fe(C12H21N2Si)2Cl]

M = 534.10

Monoclinic,

a = 34.213 (5) Å

b = 9.3555 (14) Å

c = 20.769 (4) Å

β = 122.924 (5)°

V = 5580.1 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.74 mm−1

T = 293 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.808, T max = 0.866

11193 measured reflections

4880 independent reflections

4359 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.06

4880 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018114/rk2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018114/rk2098Isup2.hkl

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

[Fe(C12H21N2Si)2Cl]	F000 = 2280
Mr = 534.10	Dx = 1.271 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7222 reflections
a = 34.213 (5) Å	θ = 2.3–27.6º
b = 9.3555 (14) Å	µ = 0.74 mm−1
c = 20.769 (4) Å	T = 293 (2) K
β = 122.924 (5)º	Prism, black
V = 5580.1 (16) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART area-detector diffractometer	4880 independent reflections
Radiation source: Fine–focus sealed tube	4359 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.031
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −40→33
Tmin = 0.808, Tmax = 0.866	k = −11→11
11193 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0505P)2 + 4.0594P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4880 reflections	Δρmax = 0.48 e Å−3
301 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: Direct	Extinction correction: none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.152240 (10)	0.34361 (3)	0.065107 (16)	0.03404 (12)
Cl1	0.22982 (2)	0.30852 (7)	0.13642 (4)	0.05195 (17)
Si1	0.14458 (2)	0.46111 (7)	0.18176 (3)	0.04116 (17)
Si2	0.12728 (2)	0.23365 (7)	−0.07896 (3)	0.04149 (17)
N1	0.12489 (6)	0.31269 (19)	0.12496 (10)	0.0340 (4)
N2	0.15405 (6)	0.5619 (2)	0.11810 (10)	0.0406 (4)
N3	0.12899 (6)	0.3964 (2)	−0.04016 (10)	0.0378 (4)
N4	0.13464 (7)	0.1293 (2)	−0.00134 (11)	0.0429 (5)
C1	0.10023 (8)	0.1984 (2)	0.13210 (11)	0.0353 (5)
C2	0.12431 (9)	0.0830 (3)	0.18117 (12)	0.0436 (5)
C3	0.09884 (11)	−0.0285 (3)	0.18479 (15)	0.0602 (7)
H3	0.1146	−0.1061	0.2165	0.072*
C4	0.05127 (12)	−0.0272 (3)	0.14302 (17)	0.0735 (9)
H4	0.0349	−0.1021	0.1471	0.088*
C5	0.02808 (10)	0.0852 (4)	0.09519 (17)	0.0655 (8)
H5	−0.0043	0.0856	0.0664	0.079*
C6	0.05161 (8)	0.1980 (3)	0.08872 (14)	0.0454 (6)
C7	0.17639 (9)	0.0764 (3)	0.22785 (15)	0.0592 (7)
H7A	0.1884	0.1382	0.2716	0.089*
H7B	0.1880	0.1067	0.1971	0.089*
H7C	0.1862	−0.0200	0.2449	0.089*
C8	0.02459 (9)	0.3161 (3)	0.03210 (17)	0.0633 (8)
H8A	−0.0076	0.2892	0.0003	0.095*
H8B	0.0369	0.3318	0.0007	0.095*
H8C	0.0273	0.4022	0.0594	0.095*
C9	0.10149 (11)	0.5424 (3)	0.19894 (18)	0.0663 (8)
H9A	0.0733	0.5628	0.1507	0.099*
H9B	0.1140	0.6295	0.2275	0.099*
H9C	0.0950	0.4770	0.2276	0.099*
C10	0.20056 (10)	0.4460 (3)	0.27514 (14)	0.0636 (8)
H10A	0.1963	0.3900	0.3096	0.095*
H10B	0.2114	0.5396	0.2963	0.095*
H10C	0.2231	0.4004	0.2680	0.095*
C11	0.19600 (10)	0.6507 (3)	0.15052 (17)	0.0588 (7)
H11A	0.1986	0.6870	0.1098	0.088*
H11B	0.2229	0.5940	0.1846	0.088*
H11C	0.1939	0.7290	0.1783	0.088*
C12	0.11329 (10)	0.6484 (3)	0.06259 (14)	0.0519 (6)
H12A	0.1105	0.7291	0.0884	0.078*
H12B	0.0856	0.5911	0.0406	0.078*
H12C	0.1173	0.6814	0.0227	0.078*
C13	0.12223 (9)	0.5265 (3)	−0.07968 (12)	0.0423 (5)
C14	0.16070 (10)	0.6008 (3)	−0.07176 (14)	0.0513 (6)
C15	0.15268 (13)	0.7255 (3)	−0.11318 (18)	0.0683 (8)
H15	0.1779	0.7744	−0.1081	0.082*
C16	0.10921 (15)	0.7785 (3)	−0.16087 (19)	0.0781 (10)
H16	0.1047	0.8606	−0.1894	0.094*
C17	0.07203 (13)	0.7101 (3)	−0.16673 (16)	0.0698 (9)
H17	0.0424	0.7488	−0.1981	0.084*
C18	0.07738 (9)	0.5847 (3)	−0.12716 (13)	0.0518 (6)
C19	0.20951 (10)	0.5485 (4)	−0.02041 (18)	0.0703 (8)
H19A	0.2145	0.4681	−0.0438	0.106*
H19B	0.2146	0.5202	0.0280	0.106*
H19C	0.2308	0.6236	−0.0124	0.106*
C20	0.03569 (10)	0.5156 (4)	−0.13425 (16)	0.0689 (8)
H20A	0.0120	0.5862	−0.1486	0.103*
H20B	0.0444	0.4740	−0.0859	0.103*
H20C	0.0240	0.4424	−0.1728	0.103*
C21	0.17490 (11)	0.1969 (4)	−0.09351 (19)	0.0697 (8)
H21A	0.1721	0.2593	−0.1325	0.105*
H21B	0.1731	0.0993	−0.1092	0.105*
H21C	0.2043	0.2130	−0.0464	0.105*
C22	0.07192 (11)	0.1936 (4)	−0.17116 (15)	0.0676 (8)
H22A	0.0464	0.1994	−0.1642	0.101*
H22B	0.0734	0.0991	−0.1878	0.101*
H22C	0.0674	0.2618	−0.2092	0.101*
C23	0.17204 (12)	0.0207 (3)	0.03273 (17)	0.0708 (9)
H23A	0.1764	−0.0137	0.0798	0.106*
H23B	0.2005	0.0628	0.0430	0.106*
H23C	0.1635	−0.0575	−0.0024	0.106*
C24	0.09130 (11)	0.0623 (3)	−0.01730 (16)	0.0653 (8)
H24A	0.0824	−0.0128	−0.0542	0.098*
H24B	0.0670	0.1328	−0.0373	0.098*
H24C	0.0962	0.0233	0.0293	0.098*

	U11	U22	U33	U12	U13	U23
Fe1	0.03341 (19)	0.0380 (2)	0.02983 (18)	0.00023 (12)	0.01659 (14)	0.00240 (12)
Cl1	0.0352 (3)	0.0610 (4)	0.0520 (4)	0.0044 (3)	0.0187 (3)	0.0056 (3)
Si1	0.0515 (4)	0.0366 (4)	0.0383 (3)	−0.0044 (3)	0.0262 (3)	−0.0041 (3)
Si2	0.0463 (4)	0.0460 (4)	0.0349 (3)	−0.0003 (3)	0.0238 (3)	−0.0015 (3)
N1	0.0364 (10)	0.0324 (10)	0.0327 (9)	−0.0003 (7)	0.0184 (8)	0.0014 (7)
N2	0.0453 (11)	0.0340 (10)	0.0378 (10)	−0.0027 (8)	0.0195 (9)	−0.0011 (8)
N3	0.0398 (10)	0.0421 (11)	0.0309 (9)	0.0008 (8)	0.0188 (8)	0.0046 (8)
N4	0.0540 (12)	0.0366 (11)	0.0417 (10)	−0.0031 (9)	0.0283 (10)	−0.0028 (8)
C1	0.0443 (13)	0.0349 (12)	0.0311 (10)	−0.0026 (9)	0.0235 (10)	−0.0021 (9)
C2	0.0594 (15)	0.0361 (13)	0.0357 (11)	−0.0013 (11)	0.0262 (11)	0.0001 (10)
C3	0.090 (2)	0.0411 (15)	0.0479 (14)	−0.0125 (14)	0.0362 (15)	0.0017 (12)
C4	0.094 (2)	0.066 (2)	0.0643 (18)	−0.0380 (18)	0.0450 (18)	−0.0039 (16)
C5	0.0549 (16)	0.082 (2)	0.0620 (17)	−0.0256 (15)	0.0330 (14)	−0.0072 (16)
C6	0.0433 (13)	0.0517 (15)	0.0446 (13)	−0.0067 (11)	0.0261 (11)	−0.0054 (11)
C7	0.0598 (17)	0.0522 (17)	0.0521 (15)	0.0127 (13)	0.0217 (13)	0.0133 (12)
C8	0.0403 (15)	0.072 (2)	0.0651 (18)	0.0058 (13)	0.0207 (13)	0.0056 (15)
C9	0.093 (2)	0.0542 (18)	0.0779 (19)	0.0006 (15)	0.0636 (19)	−0.0101 (15)
C10	0.0754 (19)	0.0621 (18)	0.0380 (13)	−0.0143 (15)	0.0210 (13)	−0.0044 (12)
C11	0.0670 (18)	0.0471 (16)	0.0627 (17)	−0.0190 (13)	0.0355 (15)	−0.0070 (13)
C12	0.0638 (17)	0.0430 (15)	0.0462 (14)	0.0108 (12)	0.0281 (13)	0.0065 (11)
C13	0.0580 (15)	0.0417 (14)	0.0306 (11)	0.0025 (11)	0.0263 (11)	0.0014 (9)
C14	0.0726 (18)	0.0434 (14)	0.0493 (14)	−0.0058 (13)	0.0406 (14)	−0.0016 (11)
C15	0.114 (3)	0.0445 (17)	0.0706 (19)	−0.0082 (17)	0.066 (2)	0.0001 (14)
C16	0.131 (3)	0.0469 (18)	0.067 (2)	0.010 (2)	0.060 (2)	0.0141 (15)
C17	0.093 (2)	0.0611 (19)	0.0468 (15)	0.0274 (17)	0.0328 (16)	0.0147 (14)
C18	0.0639 (16)	0.0548 (16)	0.0344 (12)	0.0122 (13)	0.0251 (12)	0.0048 (11)
C19	0.0643 (18)	0.073 (2)	0.079 (2)	−0.0185 (16)	0.0427 (17)	0.0017 (16)
C20	0.0528 (16)	0.090 (2)	0.0506 (15)	0.0207 (16)	0.0198 (13)	0.0096 (15)
C21	0.086 (2)	0.069 (2)	0.084 (2)	0.0023 (16)	0.0652 (19)	−0.0030 (16)
C22	0.070 (2)	0.072 (2)	0.0424 (14)	−0.0015 (15)	0.0191 (14)	−0.0119 (14)
C23	0.100 (2)	0.0492 (17)	0.0574 (16)	0.0246 (16)	0.0392 (17)	0.0058 (13)
C24	0.088 (2)	0.0653 (19)	0.0614 (16)	−0.0338 (16)	0.0529 (16)	−0.0209 (14)

Fe1—N3	1.9406 (17)	C10—H10A	0.9600
Fe1—N1	1.9412 (18)	C10—H10B	0.9600
Fe1—Cl1	2.2523 (7)	C10—H10C	0.9600
Fe1—N2	2.3050 (19)	C11—H11A	0.9600
Fe1—N4	2.3203 (19)	C11—H11B	0.9600
Si1—N1	1.7058 (18)	C11—H11C	0.9600
Si1—N2	1.791 (2)	C12—H12A	0.9600
Si1—C10	1.847 (3)	C12—H12B	0.9600
Si1—C9	1.858 (3)	C12—H12C	0.9600
Si2—N3	1.709 (2)	C13—C18	1.407 (3)
Si2—N4	1.782 (2)	C13—C14	1.417 (4)
Si2—C21	1.844 (3)	C14—C15	1.386 (4)
Si2—C22	1.858 (3)	C14—C19	1.493 (4)
N1—C1	1.419 (3)	C15—C16	1.355 (5)
N2—C11	1.467 (3)	C15—H15	0.9300
N2—C12	1.477 (3)	C16—C17	1.369 (5)
N3—C13	1.415 (3)	C16—H16	0.9300
N4—C24	1.472 (3)	C17—C18	1.386 (4)
N4—C23	1.478 (3)	C17—H17	0.9300
C1—C6	1.396 (3)	C18—C20	1.499 (4)
C1—C2	1.404 (3)	C19—H19A	0.9600
C2—C3	1.387 (4)	C19—H19B	0.9600
C2—C7	1.497 (4)	C19—H19C	0.9600
C3—C4	1.366 (4)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.366 (4)	C20—H20C	0.9600
C4—H4	0.9300	C21—H21A	0.9600
C5—C6	1.377 (4)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C8	1.508 (4)	C22—H22A	0.9600
C7—H7A	0.9600	C22—H22B	0.9600
C7—H7B	0.9600	C22—H22C	0.9600
C7—H7C	0.9600	C23—H23A	0.9600
C8—H8A	0.9600	C23—H23B	0.9600
C8—H8B	0.9600	C23—H23C	0.9600
C8—H8C	0.9600	C24—H24A	0.9600
C9—H9A	0.9600	C24—H24B	0.9600
C9—H9B	0.9600	C24—H24C	0.9600
C9—H9C	0.9600
N3—Fe1—N1	135.57 (8)	H9A—C9—H9C	109.5
N3—Fe1—Cl1	113.14 (6)	H9B—C9—H9C	109.5
N1—Fe1—Cl1	111.29 (6)	Si1—C10—H10A	109.5
N3—Fe1—N2	101.58 (7)	Si1—C10—H10B	109.5
N1—Fe1—N2	73.95 (7)	H10A—C10—H10B	109.5
Cl1—Fe1—N2	95.68 (5)	Si1—C10—H10C	109.5
N3—Fe1—N4	74.63 (7)	H10A—C10—H10C	109.5
N1—Fe1—N4	101.10 (7)	H10B—C10—H10C	109.5
Cl1—Fe1—N4	95.59 (5)	N2—C11—H11A	109.5
N2—Fe1—N4	168.71 (7)	N2—C11—H11B	109.5
N1—Si1—N2	94.59 (9)	H11A—C11—H11B	109.5
N1—Si1—C10	117.27 (12)	N2—C11—H11C	109.5
N2—Si1—C10	108.36 (11)	H11A—C11—H11C	109.5
N1—Si1—C9	114.20 (12)	H11B—C11—H11C	109.5
N2—Si1—C9	114.01 (12)	N2—C12—H12A	109.5
C10—Si1—C9	107.93 (15)	N2—C12—H12B	109.5
N3—Si2—N4	96.30 (9)	H12A—C12—H12B	109.5
N3—Si2—C21	115.89 (13)	N2—C12—H12C	109.5
N4—Si2—C21	110.08 (13)	H12A—C12—H12C	109.5
N3—Si2—C22	114.84 (12)	H12B—C12—H12C	109.5
N4—Si2—C22	112.69 (13)	C18—C13—N3	120.8 (2)
C21—Si2—C22	106.86 (15)	C18—C13—C14	118.8 (2)
C1—N1—Si1	125.09 (14)	N3—C13—C14	120.4 (2)
C1—N1—Fe1	134.44 (14)	C15—C14—C13	118.9 (3)
Si1—N1—Fe1	100.08 (9)	C15—C14—C19	119.1 (3)
C11—N2—C12	108.7 (2)	C13—C14—C19	122.0 (2)
C11—N2—Si1	118.92 (16)	C16—C15—C14	122.0 (3)
C12—N2—Si1	113.07 (16)	C16—C15—H15	119.0
C11—N2—Fe1	119.09 (16)	C14—C15—H15	119.0
C12—N2—Fe1	110.11 (14)	C15—C16—C17	119.5 (3)
Si1—N2—Fe1	85.25 (8)	C15—C16—H16	120.3
C13—N3—Si2	122.68 (14)	C17—C16—H16	120.3
C13—N3—Fe1	135.24 (15)	C16—C17—C18	121.7 (3)
Si2—N3—Fe1	101.10 (9)	C16—C17—H17	119.1
C24—N4—C23	108.6 (2)	C18—C17—H17	119.1
C24—N4—Si2	113.57 (17)	C17—C18—C13	119.1 (3)
C23—N4—Si2	117.99 (17)	C17—C18—C20	119.7 (3)
C24—N4—Fe1	113.94 (16)	C13—C18—C20	121.3 (2)
C23—N4—Fe1	115.57 (16)	C14—C19—H19A	109.5
Si2—N4—Fe1	85.87 (8)	C14—C19—H19B	109.5
C6—C1—C2	119.3 (2)	H19A—C19—H19B	109.5
C6—C1—N1	120.2 (2)	C14—C19—H19C	109.5
C2—C1—N1	120.5 (2)	H19A—C19—H19C	109.5
C3—C2—C1	118.7 (2)	H19B—C19—H19C	109.5
C3—C2—C7	119.7 (2)	C18—C20—H20A	109.5
C1—C2—C7	121.6 (2)	C18—C20—H20B	109.5
C4—C3—C2	121.7 (3)	H20A—C20—H20B	109.5
C4—C3—H3	119.1	C18—C20—H20C	109.5
C2—C3—H3	119.1	H20A—C20—H20C	109.5
C5—C4—C3	119.3 (3)	H20B—C20—H20C	109.5
C5—C4—H4	120.4	Si2—C21—H21A	109.5
C3—C4—H4	120.4	Si2—C21—H21B	109.5
C4—C5—C6	121.4 (3)	H21A—C21—H21B	109.5
C4—C5—H5	119.3	Si2—C21—H21C	109.5
C6—C5—H5	119.3	H21A—C21—H21C	109.5
C5—C6—C1	119.6 (2)	H21B—C21—H21C	109.5
C5—C6—C8	119.6 (2)	Si2—C22—H22A	109.5
C1—C6—C8	120.8 (2)	Si2—C22—H22B	109.5
C2—C7—H7A	109.5	H22A—C22—H22B	109.5
C2—C7—H7B	109.5	Si2—C22—H22C	109.5
H7A—C7—H7B	109.5	H22A—C22—H22C	109.5
C2—C7—H7C	109.5	H22B—C22—H22C	109.5
H7A—C7—H7C	109.5	N4—C23—H23A	109.5
H7B—C7—H7C	109.5	N4—C23—H23B	109.5
C6—C8—H8A	109.5	H23A—C23—H23B	109.5
C6—C8—H8B	109.5	N4—C23—H23C	109.5
H8A—C8—H8B	109.5	H23A—C23—H23C	109.5
C6—C8—H8C	109.5	H23B—C23—H23C	109.5
H8A—C8—H8C	109.5	N4—C24—H24A	109.5
H8B—C8—H8C	109.5	N4—C24—H24B	109.5
Si1—C9—H9A	109.5	H24A—C24—H24B	109.5
Si1—C9—H9B	109.5	N4—C24—H24C	109.5
H9A—C9—H9B	109.5	H24A—C24—H24C	109.5
Si1—C9—H9C	109.5	H24B—C24—H24C	109.5