Dibromido[(tert-butyl-amino)dimeth-yl(piperidin-1-ylmeth-yl)silane-κN,N']zinc(II).

The title compound, [ZnBr(2)(C(12)H(28)N(2)Si)], is an example of a neutral coordination compound of a bidentate ligand to a metal centre with the Zn atom being coordinated by two Br and two N atoms, yielding a slightly distorted tetra-hedral coordination environment.

Related literature

For the synthesis and structure of cis-(2-amino-1,1-dimethyl­ethylamine)dichloro­palladium(II) ethanol hemisolvate, see: Farrugia et al. (2001 ▶). For niobium and tantalum complexes of silylamides, see: Herrmann et al. (1992 ▶). For the synthesis and structure of Bu2Si=N-SiClBu2, see: Lerner et al. (2005 ▶); for syntheses, structures and properties of chiral zinc halide catalysts, see: Mimoun et al. (1999 ▶). For the structure and reactivity of lithia­ted benzyl­silanes, see: Ott et al. (2008 ▶). For syntheses and structures of bis­{[diphen­yl(piperidinometh­yl)­sil­yl]meth­yl}cadmium and -magnesium, see: Strohmann & Schildbach (2002 ▶). For a highly diastereomerically enriched, silyl-substituted alkyl lithium, see: Strohmann et al. (2005 ▶). For the synthesis and structure of a monolithia­ted allyl­silane and its related 1,3-dilithia­ted allyl­silane, see: Strohmann et al. (2006 ▶). For the synthesis and structure of a lithia­ted [(benzyl­silyl)meth­yl]amine, see: Strohmann et al. (2002 ▶).

Experimental

Crystal data

[ZnBr2(C12H28N2Si)]

M = 453.64

Monoclinic,

a = 12.0284 (4) Å

b = 10.6505 (3) Å

c = 14.5633 (5) Å

β = 109.752 (4)°

V = 1755.91 (10) Å3

Z = 4

Mo Kα radiation

μ = 6.01 mm−1

T = 123 K

0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.698, T max = 1.000 (expected range = 0.210–0.301)

17826 measured reflections

3440 independent reflections

2673 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.035

S = 1.04

3440 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018364/fi2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018364/fi2078Isup2.hkl

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

[ZnBr2(C12H28N2Si)]	F(000) = 912
Mr = 453.64	Dx = 1.716 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9282 reflections
a = 12.0284 (4) Å	θ = 2.4–29.1°
b = 10.6505 (3) Å	µ = 6.01 mm−1
c = 14.5633 (5) Å	T = 123 K
β = 109.752 (4)°	Block, colourless
V = 1755.91 (10) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur S diffractometer	2673 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.034
graphite	θmax = 26.0°, θmin = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.698, Tmax = 1.000	l = −17→17
17826 measured reflections	1 standard reflections every 50 reflections
3440 independent reflections	intensity decay: none

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.035	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.012P)2] where P = (Fo2 + 2Fc2)/3
3440 reflections	(Δ/σ)max = 0.002
172 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. CrysAlis RED, Oxford Diffraction Ltd. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	0.034333 (19)	0.34304 (2)	0.425367 (16)	0.02008 (7)
Br2	0.36966 (2)	0.21717 (2)	0.546307 (18)	0.02735 (7)
C1	0.43775 (18)	0.4264 (2)	0.80678 (16)	0.0251 (6)
H1A	0.4537	0.3636	0.7637	0.038*
H1B	0.4397	0.3863	0.8679	0.038*
H1C	0.4980	0.4924	0.8209	0.038*
C2	0.2739 (2)	0.6418 (2)	0.80978 (17)	0.0296 (6)
H2A	0.3418	0.6969	0.8175	0.044*
H2B	0.2703	0.6207	0.8742	0.044*
H2C	0.2011	0.6850	0.7714	0.044*
C3	0.16458 (18)	0.3884 (2)	0.74214 (15)	0.0168 (5)
H3A	0.1720	0.3654	0.8098	0.020*
H3B	0.0894	0.4349	0.7138	0.020*
C4	0.03415 (18)	0.2212 (2)	0.65665 (15)	0.0178 (5)
H4A	−0.0202	0.2816	0.6117	0.021*
H4B	0.0116	0.2148	0.7159	0.021*
C5	0.0203 (2)	0.0941 (2)	0.60787 (16)	0.0234 (6)
H5A	0.0380	0.1013	0.5465	0.028*
H5B	−0.0625	0.0656	0.5912	0.028*
C6	0.10247 (19)	−0.0026 (2)	0.67401 (17)	0.0246 (6)
H6A	0.0809	−0.0159	0.7331	0.029*
H6B	0.0954	−0.0837	0.6394	0.029*
C7	0.22848 (19)	0.0459 (2)	0.70248 (17)	0.0215 (6)
H7A	0.2824	−0.0132	0.7490	0.026*
H7B	0.2522	0.0504	0.6437	0.026*
C8	0.23979 (19)	0.1747 (2)	0.74873 (15)	0.0176 (5)
H8A	0.2232	0.1680	0.8107	0.021*
H8B	0.3222	0.2043	0.7646	0.021*
C9	0.32287 (19)	0.5977 (2)	0.56932 (16)	0.0198 (5)
C10	0.2842 (2)	0.5668 (2)	0.46137 (16)	0.0271 (6)
H10A	0.3038	0.4793	0.4529	0.041*
H10B	0.3250	0.6223	0.4295	0.041*
H10C	0.1987	0.5790	0.4320	0.041*
C11	0.2945 (2)	0.7356 (2)	0.58157 (17)	0.0275 (6)
H11A	0.2090	0.7489	0.5533	0.041*
H11B	0.3349	0.7893	0.5481	0.041*
H11C	0.3214	0.7569	0.6511	0.041*
C12	0.45464 (18)	0.5736 (2)	0.61593 (17)	0.0283 (6)
H12A	0.4815	0.6038	0.6835	0.042*
H12B	0.4973	0.6182	0.5792	0.042*
H12C	0.4701	0.4833	0.6152	0.042*
H1N	0.1857 (18)	0.544 (2)	0.5961 (15)	0.024 (7)*
N1	0.25541 (17)	0.51356 (18)	0.61717 (13)	0.0169 (5)
N2	0.15788 (14)	0.26976 (16)	0.68447 (12)	0.0126 (4)
Si	0.29025 (5)	0.49627 (6)	0.74618 (5)	0.01692 (15)
Zn	0.20862 (2)	0.32732 (2)	0.565755 (18)	0.01447 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.01765 (13)	0.02519 (15)	0.01490 (13)	−0.00001 (11)	0.00222 (10)	0.00006 (11)
Br2	0.02695 (14)	0.02831 (15)	0.03360 (15)	0.01126 (12)	0.01917 (12)	0.00731 (13)
C1	0.0218 (14)	0.0238 (15)	0.0254 (15)	−0.0039 (11)	0.0025 (12)	0.0022 (12)
C2	0.0291 (15)	0.0299 (16)	0.0306 (16)	−0.0056 (12)	0.0112 (13)	−0.0105 (12)
C3	0.0175 (13)	0.0198 (14)	0.0152 (13)	0.0025 (11)	0.0081 (11)	−0.0013 (11)
C4	0.0144 (12)	0.0245 (14)	0.0156 (13)	−0.0032 (11)	0.0062 (11)	0.0008 (11)
C5	0.0199 (14)	0.0276 (16)	0.0214 (14)	−0.0114 (12)	0.0052 (12)	−0.0033 (12)
C6	0.0311 (15)	0.0174 (14)	0.0265 (15)	−0.0076 (12)	0.0115 (13)	−0.0007 (11)
C7	0.0254 (14)	0.0150 (14)	0.0252 (14)	0.0025 (11)	0.0099 (12)	0.0047 (11)
C8	0.0152 (12)	0.0183 (14)	0.0175 (13)	0.0015 (11)	0.0030 (10)	0.0054 (11)
C9	0.0178 (13)	0.0194 (14)	0.0220 (14)	−0.0037 (11)	0.0065 (11)	0.0027 (11)
C10	0.0347 (16)	0.0228 (15)	0.0268 (15)	−0.0032 (12)	0.0144 (13)	0.0059 (12)
C11	0.0279 (15)	0.0201 (15)	0.0353 (16)	−0.0060 (12)	0.0118 (13)	−0.0006 (12)
C12	0.0176 (14)	0.0345 (17)	0.0342 (16)	−0.0016 (12)	0.0106 (13)	0.0053 (12)
N1	0.0135 (11)	0.0187 (12)	0.0190 (11)	−0.0038 (9)	0.0064 (10)	−0.0013 (9)
N2	0.0101 (10)	0.0145 (11)	0.0121 (10)	−0.0007 (8)	0.0023 (8)	−0.0006 (8)
Si	0.0168 (4)	0.0177 (4)	0.0158 (4)	−0.0018 (3)	0.0049 (3)	−0.0033 (3)
Zn	0.01415 (14)	0.01651 (15)	0.01335 (15)	0.00006 (12)	0.00541 (12)	−0.00062 (12)

Br1—Zn	2.3887 (4)	C7—C8	1.513 (3)
Br2—Zn	2.3622 (3)	C7—H7A	0.9900
C1—Si	1.850 (2)	C7—H7B	0.9900
C1—H1A	0.9800	C8—N2	1.500 (2)
C1—H1B	0.9800	C8—H8A	0.9900
C1—H1C	0.9800	C8—H8B	0.9900
C2—Si	1.850 (2)	C9—C10	1.517 (3)
C2—H2A	0.9800	C9—C12	1.520 (3)
C2—H2B	0.9800	C9—N1	1.526 (3)
C2—H2C	0.9800	C9—C11	1.532 (3)
C3—N2	1.504 (3)	C10—H10A	0.9800
C3—Si	1.884 (2)	C10—H10B	0.9800
C3—H3A	0.9900	C10—H10C	0.9800
C3—H3B	0.9900	C11—H11A	0.9800
C4—N2	1.496 (2)	C11—H11B	0.9800
C4—C5	1.512 (3)	C11—H11C	0.9800
C4—H4A	0.9900	C12—H12A	0.9800
C4—H4B	0.9900	C12—H12B	0.9800
C5—C6	1.524 (3)	C12—H12C	0.9800
C5—H5A	0.9900	N1—Si	1.7909 (19)
C5—H5B	0.9900	N1—Zn	2.1276 (19)
C6—C7	1.520 (3)	N1—H1N	0.85 (2)
C6—H6A	0.9900	N2—Zn	2.1096 (16)
C6—H6B	0.9900
Si—C1—H1A	109.5	C10—C9—C12	109.55 (19)
Si—C1—H1B	109.5	C10—C9—N1	108.78 (18)
H1A—C1—H1B	109.5	C12—C9—N1	109.40 (18)
Si—C1—H1C	109.5	C10—C9—C11	109.01 (19)
H1A—C1—H1C	109.5	C12—C9—C11	110.46 (19)
H1B—C1—H1C	109.5	N1—C9—C11	109.62 (17)
Si—C2—H2A	109.5	C9—C10—H10A	109.5
Si—C2—H2B	109.5	C9—C10—H10B	109.5
H2A—C2—H2B	109.5	H10A—C10—H10B	109.5
Si—C2—H2C	109.5	C9—C10—H10C	109.5
H2A—C2—H2C	109.5	H10A—C10—H10C	109.5
H2B—C2—H2C	109.5	H10B—C10—H10C	109.5
N2—C3—Si	114.88 (13)	C9—C11—H11A	109.5
N2—C3—H3A	108.5	C9—C11—H11B	109.5
Si—C3—H3A	108.5	H11A—C11—H11B	109.5
N2—C3—H3B	108.5	C9—C11—H11C	109.5
Si—C3—H3B	108.5	H11A—C11—H11C	109.5
H3A—C3—H3B	107.5	H11B—C11—H11C	109.5
N2—C4—C5	112.22 (17)	C9—C12—H12A	109.5
N2—C4—H4A	109.2	C9—C12—H12B	109.5
C5—C4—H4A	109.2	H12A—C12—H12B	109.5
N2—C4—H4B	109.2	C9—C12—H12C	109.5
C5—C4—H4B	109.2	H12A—C12—H12C	109.5
H4A—C4—H4B	107.9	H12B—C12—H12C	109.5
C4—C5—C6	111.29 (19)	C9—N1—Si	124.57 (15)
C4—C5—H5A	109.4	C9—N1—Zn	120.32 (13)
C6—C5—H5A	109.4	Si—N1—Zn	102.34 (9)
C4—C5—H5B	109.4	C9—N1—H1N	102.9 (15)
C6—C5—H5B	109.4	Si—N1—H1N	105.6 (14)
H5A—C5—H5B	108.0	Zn—N1—H1N	96.6 (16)
C7—C6—C5	108.47 (18)	C4—N2—C8	108.62 (16)
C7—C6—H6A	110.0	C4—N2—C3	107.58 (15)
C5—C6—H6A	110.0	C8—N2—C3	108.60 (16)
C7—C6—H6B	110.0	C4—N2—Zn	114.54 (13)
C5—C6—H6B	110.0	C8—N2—Zn	113.37 (12)
H6A—C6—H6B	108.4	C3—N2—Zn	103.75 (12)
C8—C7—C6	111.13 (18)	N1—Si—C1	112.86 (10)
C8—C7—H7A	109.4	N1—Si—C2	114.35 (10)
C6—C7—H7A	109.4	C1—Si—C2	110.18 (11)
C8—C7—H7B	109.4	N1—Si—C3	97.42 (9)
C6—C7—H7B	109.4	C1—Si—C3	113.57 (10)
H7A—C7—H7B	108.0	C2—Si—C3	107.88 (10)
N2—C8—C7	113.13 (18)	N2—Zn—N1	95.62 (7)
N2—C8—H8A	109.0	N2—Zn—Br2	115.47 (5)
C7—C8—H8A	109.0	N1—Zn—Br2	112.03 (5)
N2—C8—H8B	109.0	N2—Zn—Br1	107.97 (5)
C7—C8—H8B	109.0	N1—Zn—Br1	106.69 (5)
H8A—C8—H8B	107.8	Br2—Zn—Br1	116.759 (13)