Chlorido{N-[(diethyl-amino)-dimethyl-sil-yl]anilido-κN}(N,N,N',N'-tetra-methyl-ethane-1,2-diamine-κ(2) N,N')iron(II).

In the title iron(II) complex, [Fe(C12H21N2Si)Cl(C6H16N2)], the Fe(II) cation is coordinated by two N atoms from the tetramethylethane-1,2-diamine ligand [Fe-N = 2.191 (5) and 2.215 (4) Å], one N atom from the N-[(diethyl-amino)-dimethyl-sil-yl]anilide ligand [Fe-N = 1.943 (4) Å] and a chloride ligand [Fe-Cl = 2.2798 (16) Å] in a distorted tetra-hedral geometry. The N-Si-N angle is 113.9 (3)°. The crystal packing exhibits no short inter-molecular contacts.

Related literature

For FeII complexes with n class="Chemical">N-donor ligand and utility in fixation of dinitro­gen, see: Smith et al. (2001 ▶); Rodriguez et al. (2011 ▶). For reviews of related metal amides, see: Holm et al. (1996 ▶); Kempe (2000 ▶). For catalytic applications of the related N-silylated anilido group 4 metal compounds towards olefin polymerization, see: Gibson et al. (1998 ▶); Hill & Hitchcock (2002 ▶); Yuan et al. (2010 ▶). For related organometallic compounds with analogous anilido ligands, see: Schumann et al. (2000 ▶); Chen (2008 ▶, 2009 ▶).

Experimental

Crystal data

[Fe(n class="CellLine">C12H21N2Si)Cl(C6H16N2)]

M = 428.91

Monoclinic,

a = 16.2317 (10) Å

b = 10.7821 (6) Å

c = 14.2098 (8) Å

β = 105.157 (1)°

V = 2400.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.826, T max = 0.890

12665 measured reflections

4222 independent reflections

2584 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.190

S = 1.02

4222 reflections

226 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044741/cv5351sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044741/cv5351Isup2.hkl

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

[Fe(C12H21N2Si)Cl(C6H16N2)]	F(000) = 920
Mr = 428.91	Dx = 1.187 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3162 reflections
a = 16.2317 (10) Å	θ = 2.2–25.3°
b = 10.7821 (6) Å	µ = 0.80 mm−1
c = 14.2098 (8) Å	T = 293 K
β = 105.157 (1)°	Block, colourless
V = 2400.4 (2) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker SMART area-detector diffractometer	4222 independent reflections
Radiation source: fine-focus sealed tube	2584 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scan	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→14
Tmin = 0.826, Tmax = 0.890	k = −11→12
12665 measured reflections	l = −15→16

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1016P)2 + 1.3944P] where P = (Fo2 + 2Fc2)/3
4222 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.71 e Å−3
14 restraints	Δρmin = −0.65 e Å−3

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	0.82680 (5)	0.53246 (6)	0.32605 (5)	0.0438 (3)
Si1	0.67995 (11)	0.45040 (15)	0.42532 (12)	0.0577 (5)
Cl1	0.89234 (12)	0.69105 (14)	0.42333 (13)	0.0771 (5)
N1	0.7543 (3)	0.4097 (4)	0.3648 (3)	0.0482 (11)
N2	0.5867 (4)	0.3658 (6)	0.3912 (5)	0.0988 (17)
N3	0.7721 (3)	0.6122 (4)	0.1794 (3)	0.0625 (13)
N4	0.9258 (3)	0.4720 (4)	0.2568 (3)	0.0591 (12)
C1	0.7874 (3)	0.2877 (4)	0.3770 (3)	0.0434 (12)
C2	0.8678 (4)	0.2640 (5)	0.4374 (4)	0.0542 (14)
H2A	0.8987	0.3286	0.4734	0.065*
C3	0.9035 (4)	0.1458 (5)	0.4455 (4)	0.0598 (15)
H3A	0.9585	0.1331	0.4847	0.072*
C4	0.8583 (5)	0.0484 (5)	0.3961 (5)	0.0659 (17)
H4A	0.8816	−0.0309	0.4024	0.079*
C5	0.7778 (5)	0.0696 (5)	0.3371 (5)	0.0732 (19)
H5A	0.7464	0.0038	0.3032	0.088*
C6	0.7430 (4)	0.1871 (5)	0.3275 (4)	0.0622 (16)
H6A	0.6885	0.1992	0.2869	0.075*
C7	0.7246 (5)	0.4311 (8)	0.5602 (5)	0.095 (2)
H7A	0.7376	0.3452	0.5749	0.142*
H7B	0.6833	0.4585	0.5933	0.142*
H7C	0.7757	0.4795	0.5816	0.142*
C8	0.6537 (5)	0.6178 (6)	0.3978 (6)	0.084 (2)
H8A	0.6307	0.6283	0.3288	0.126*
H8B	0.7046	0.6667	0.4193	0.126*
H8C	0.6124	0.6442	0.4312	0.126*
C9	0.5430 (6)	0.3069 (9)	0.4576 (7)	0.1194 (19)
H9A	0.5635	0.3436	0.5218	0.143*
H9B	0.4823	0.3241	0.4349	0.143*
C10	0.5550 (7)	0.1785 (11)	0.4652 (9)	0.166 (3)
H10A	0.5250	0.1455	0.5095	0.250*
H10B	0.6148	0.1607	0.4891	0.250*
H10C	0.5335	0.1412	0.4022	0.250*
C11	0.5383 (5)	0.3602 (8)	0.2873 (7)	0.102 (3)
H11A	0.5274	0.2740	0.2685	0.123*
H11B	0.5730	0.3952	0.2478	0.123*
C12	0.4542 (6)	0.4289 (10)	0.2661 (11)	0.170 (5)
H12A	0.4257	0.4217	0.1980	0.255*
H12B	0.4645	0.5149	0.2827	0.255*
H12C	0.4190	0.3939	0.3041	0.255*
C13	0.6850 (5)	0.5640 (8)	0.1353 (6)	0.106 (3)
H13A	0.6629	0.6002	0.0720	0.159*
H13B	0.6484	0.5852	0.1762	0.159*
H13C	0.6871	0.4755	0.1293	0.159*
C14	0.7685 (6)	0.7484 (6)	0.1864 (5)	0.099 (3)
H14A	0.7449	0.7828	0.1227	0.148*
H14B	0.8251	0.7804	0.2126	0.148*
H14C	0.7333	0.7708	0.2285	0.148*
C15	0.8280 (5)	0.5752 (7)	0.1178 (5)	0.079 (2)
H15A	0.8251	0.6371	0.0676	0.095*
H15B	0.8083	0.4970	0.0861	0.095*
C16	0.9170 (5)	0.5619 (6)	0.1763 (5)	0.079 (2)
H16A	0.9380	0.6421	0.2032	0.095*
H16B	0.9519	0.5351	0.1342	0.095*
C17	1.0132 (5)	0.4808 (8)	0.3220 (6)	0.097 (2)
H17A	1.0536	0.4534	0.2878	0.145*
H17B	1.0175	0.4293	0.3782	0.145*
H17C	1.0251	0.5653	0.3423	0.145*
C18	0.9109 (5)	0.3440 (6)	0.2185 (5)	0.087 (2)
H18A	0.9555	0.3209	0.1891	0.131*
H18B	0.8569	0.3401	0.1707	0.131*
H18C	0.9106	0.2882	0.2710	0.131*

	U11	U22	U33	U12	U13	U23
Fe1	0.0509 (5)	0.0347 (4)	0.0478 (4)	−0.0028 (3)	0.0164 (3)	−0.0015 (3)
Si1	0.0617 (11)	0.0552 (10)	0.0614 (10)	0.0002 (8)	0.0253 (9)	−0.0016 (7)
Cl1	0.0842 (12)	0.0554 (9)	0.0855 (11)	−0.0140 (8)	0.0114 (10)	−0.0227 (8)
N1	0.052 (3)	0.035 (2)	0.060 (3)	−0.001 (2)	0.019 (2)	0.000 (2)
N2	0.086 (4)	0.094 (4)	0.127 (4)	−0.019 (3)	0.047 (3)	0.011 (3)
N3	0.068 (3)	0.060 (3)	0.057 (3)	0.007 (3)	0.013 (3)	0.010 (2)
N4	0.063 (3)	0.060 (3)	0.063 (3)	0.006 (2)	0.030 (3)	0.004 (2)
C1	0.049 (3)	0.042 (3)	0.043 (3)	−0.002 (2)	0.018 (3)	−0.002 (2)
C2	0.066 (4)	0.047 (3)	0.052 (3)	−0.005 (3)	0.019 (3)	−0.005 (2)
C3	0.065 (4)	0.062 (4)	0.055 (3)	0.011 (3)	0.019 (3)	0.012 (3)
C4	0.087 (5)	0.043 (3)	0.076 (4)	0.009 (3)	0.037 (4)	0.007 (3)
C5	0.080 (5)	0.041 (3)	0.103 (5)	−0.010 (3)	0.032 (4)	−0.018 (3)
C6	0.057 (4)	0.054 (3)	0.073 (4)	−0.005 (3)	0.012 (3)	−0.016 (3)
C7	0.108 (6)	0.116 (6)	0.065 (4)	0.014 (5)	0.032 (4)	−0.007 (4)
C8	0.084 (5)	0.062 (4)	0.119 (6)	0.013 (4)	0.050 (5)	−0.002 (4)
C9	0.107 (4)	0.114 (4)	0.143 (5)	−0.024 (4)	0.043 (4)	0.020 (4)
C10	0.151 (6)	0.146 (6)	0.186 (6)	−0.016 (6)	0.015 (6)	0.038 (6)
C11	0.062 (5)	0.099 (6)	0.135 (7)	−0.013 (4)	0.006 (5)	0.007 (5)
C12	0.087 (7)	0.137 (9)	0.260 (15)	0.010 (7)	0.001 (9)	0.013 (9)
C13	0.087 (6)	0.140 (7)	0.075 (5)	−0.002 (5)	−0.006 (5)	0.015 (5)
C14	0.131 (7)	0.059 (4)	0.102 (6)	0.027 (4)	0.022 (5)	0.034 (4)
C15	0.098 (6)	0.083 (5)	0.063 (4)	0.013 (4)	0.034 (4)	0.021 (3)
C16	0.092 (6)	0.076 (4)	0.085 (5)	0.002 (4)	0.049 (4)	0.016 (4)
C17	0.060 (5)	0.128 (7)	0.102 (6)	0.022 (4)	0.022 (4)	0.007 (5)
C18	0.128 (7)	0.072 (4)	0.082 (5)	0.022 (4)	0.064 (5)	−0.001 (4)

Fe1—N1	1.943 (4)	C8—H8B	0.9600
Fe1—N4	2.191 (5)	C8—H8C	0.9600
Fe1—N3	2.215 (4)	C9—C10	1.399 (11)
Fe1—Cl1	2.2798 (16)	C9—H9A	0.9700
Si1—N1	1.713 (5)	C9—H9B	0.9700
Si1—N2	1.726 (7)	C10—H10A	0.9600
Si1—C8	1.872 (7)	C10—H10B	0.9600
Si1—C7	1.876 (7)	C10—H10C	0.9600
N1—C1	1.414 (6)	C11—C12	1.513 (11)
N2—C9	1.464 (10)	C11—H11A	0.9700
N2—C11	1.481 (9)	C11—H11B	0.9700
N3—C15	1.470 (8)	C12—H12A	0.9600
N3—C14	1.474 (8)	C12—H12B	0.9600
N3—C13	1.483 (9)	C12—H12C	0.9600
N4—C16	1.477 (8)	C13—H13A	0.9600
N4—C18	1.479 (8)	C13—H13B	0.9600
N4—C17	1.481 (9)	C13—H13C	0.9600
C1—C2	1.386 (7)	C14—H14A	0.9600
C1—C6	1.387 (7)	C14—H14B	0.9600
C2—C3	1.392 (8)	C14—H14C	0.9600
C2—H2A	0.9300	C15—C16	1.473 (10)
C3—C4	1.365 (8)	C15—H15A	0.9700
C3—H3A	0.9300	C15—H15B	0.9700
C4—C5	1.375 (9)	C16—H16A	0.9700
C4—H4A	0.9300	C16—H16B	0.9700
C5—C6	1.379 (8)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—H6A	0.9300	C17—H17C	0.9600
C7—H7A	0.9600	C18—H18A	0.9600
C7—H7B	0.9600	C18—H18B	0.9600
C7—H7C	0.9600	C18—H18C	0.9600
C8—H8A	0.9600
N1—Fe1—N4	119.58 (18)	C10—C9—N2	113.4 (9)
N1—Fe1—N3	114.07 (19)	C10—C9—H9A	108.9
N4—Fe1—N3	81.55 (19)	N2—C9—H9A	108.9
N1—Fe1—Cl1	124.06 (14)	C10—C9—H9B	108.9
N4—Fe1—Cl1	102.41 (14)	N2—C9—H9B	108.9
N3—Fe1—Cl1	106.74 (14)	H9A—C9—H9B	107.7
N1—Si1—N2	113.9 (3)	C9—C10—H10A	109.5
N1—Si1—C8	107.1 (3)	C9—C10—H10B	109.5
N2—Si1—C8	108.4 (3)	H10A—C10—H10B	109.5
N1—Si1—C7	110.5 (3)	C9—C10—H10C	109.5
N2—Si1—C7	107.7 (4)	H10A—C10—H10C	109.5
C8—Si1—C7	109.1 (4)	H10B—C10—H10C	109.5
C1—N1—Si1	118.1 (3)	N2—C11—C12	113.2 (9)
C1—N1—Fe1	115.5 (3)	N2—C11—H11A	108.9
Si1—N1—Fe1	121.7 (2)	C12—C11—H11A	108.9
C9—N2—C11	113.9 (7)	N2—C11—H11B	108.9
C9—N2—Si1	125.8 (6)	C12—C11—H11B	108.9
C11—N2—Si1	119.9 (5)	H11A—C11—H11B	107.7
C15—N3—C14	110.7 (5)	C11—C12—H12A	109.5
C15—N3—C13	108.8 (6)	C11—C12—H12B	109.5
C14—N3—C13	109.1 (6)	H12A—C12—H12B	109.5
C15—N3—Fe1	107.3 (4)	C11—C12—H12C	109.5
C14—N3—Fe1	109.6 (4)	H12A—C12—H12C	109.5
C13—N3—Fe1	111.4 (4)	H12B—C12—H12C	109.5
C16—N4—C18	110.7 (5)	N3—C13—H13A	109.5
C16—N4—C17	109.0 (6)	N3—C13—H13B	109.5
C18—N4—C17	109.1 (6)	H13A—C13—H13B	109.5
C16—N4—Fe1	102.6 (4)	N3—C13—H13C	109.5
C18—N4—Fe1	112.0 (4)	H13A—C13—H13C	109.5
C17—N4—Fe1	113.2 (4)	H13B—C13—H13C	109.5
C2—C1—C6	116.7 (5)	N3—C14—H14A	109.5
C2—C1—N1	120.8 (4)	N3—C14—H14B	109.5
C6—C1—N1	122.4 (5)	H14A—C14—H14B	109.5
C1—C2—C3	121.6 (5)	N3—C14—H14C	109.5
C1—C2—H2A	119.2	H14A—C14—H14C	109.5
C3—C2—H2A	119.2	H14B—C14—H14C	109.5
C4—C3—C2	120.3 (6)	N3—C15—C16	110.9 (6)
C4—C3—H3A	119.8	N3—C15—H15A	109.5
C2—C3—H3A	119.8	C16—C15—H15A	109.5
C3—C4—C5	118.9 (6)	N3—C15—H15B	109.5
C3—C4—H4A	120.5	C16—C15—H15B	109.5
C5—C4—H4A	120.5	H15A—C15—H15B	108.0
C4—C5—C6	120.8 (6)	C15—C16—N4	112.5 (6)
C4—C5—H5A	119.6	C15—C16—H16A	109.1
C6—C5—H5A	119.6	N4—C16—H16A	109.1
C5—C6—C1	121.6 (6)	C15—C16—H16B	109.1
C5—C6—H6A	119.2	N4—C16—H16B	109.1
C1—C6—H6A	119.2	H16A—C16—H16B	107.8
Si1—C7—H7A	109.5	N4—C17—H17A	109.5
Si1—C7—H7B	109.5	N4—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
Si1—C7—H7C	109.5	N4—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
Si1—C8—H8A	109.5	N4—C18—H18A	109.5
Si1—C8—H8B	109.5	N4—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
Si1—C8—H8C	109.5	N4—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5