metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages m69-m70

catena-Poly[[(N,N-di­methyl­cyanamide-κN)lithium]-μ3-bromido]

aInstitute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China
*Correspondence e-mail: mszhou@sxu.edu.cn

(Received 13 January 2014; accepted 23 January 2014; online 29 January 2014)

The title complex, [LiBr(C3H6N2)]n, is the unexpected product of a reaction beteween (Dipp)N(Li)SiMe3 (Dipp = 2,6-diiso­propyl­phen­yl), Me2NCN and CuBr. The compound is a one-dimensional polymer with a step structure derived from the association of inversion dimers, formed by bromido ligands bridging two Li+ cations, each of which carries a di­methyl­cyanamide ligand. The planar (LiBr)2 unit of the polymer core has a regular rhombic shape [Li—Br—Li 77.55 (16)° and Br—Li—Br 102.45 (16)°]. These (LiBr·NCNMe2)2 dimers represent the repeat unit of a polymer system propagated by additional Br—Li and Li—Br bonds generating an infinite step structure along the a-axis direction.

Related literature

For examples of lithium halides solvated by Lewis bases, see: Snaith & Wright (1995[Snaith, R. & Wright, D. S. (1995). In Lithium Chemistry: A Theoretical and Experimental Overview, edited by A.-M. Sapse & P. von R. Schleyer, pp. 227-294. New York: Wiley.]); Mulvey (1991[Mulvey, R. E. (1991). Chem. Soc. Rev. 20, 167-209.]); Raston, Skelton et al. (1988[Raston, C. L., Skelton, B. W., Whitaker, C. R. & White, A. H. (1988). Aust. J. Chem. 41, 1925-1934.]), Raston, Whitaker & White (1988[Raston, C. L., Whitaker, C. R. & White, A. H. (1988). J. Chem. Soc. Dalton Trans. pp. 991-995.], 1989a[Raston, C. L., Whitaker, C. R. & White, A. H. (1989a). Inorg. Chem. 28, 163-165.],b[Raston, C. L., Whitaker, C. R. & White, A. H. (1989b). Aust. J. Chem. 42, 201-207.]); Edwards et al. (1993[Edwards, A. J., Paver, M. A., Raithby, P. R., Russell, C. A. & Wright, D. S. (1993). J. Chem. Soc. Dalton Trans. pp. 3265-3266.]); Neumann et al. (1995[Neumann, F., Hampel, F. & Schleyer, P. von R. (1995). Inorg. Chem. 34, 6553-6555.]); Gregory et al. (1991[Gregory, K., Schleyer, P. von R. & Snaith, R. (1991). Adv. Inorg. Chem. 37, 47-142.]). For related crystal structures, see: Edwards et al. (1993[Edwards, A. J., Paver, M. A., Raithby, P. R., Russell, C. A. & Wright, D. S. (1993). J. Chem. Soc. Dalton Trans. pp. 3265-3266.]); Raston, Skelton et al. (1988[Raston, C. L., Skelton, B. W., Whitaker, C. R. & White, A. H. (1988). Aust. J. Chem. 41, 1925-1934.]). A 1,3,5,7-tetra­aza­hepta­trien­yl–lithium salt was reported by Boesveld et al. (2009[Boesveld, W. M., Hitchcock, P. B. & Lappert, M. F. (2009). Inorg. Chem. 48, 11444-11450.])

[Scheme 1]

Experimental

Crystal data
  • [LiBr(C3H6N2)]

  • Mr = 156.85

  • Monoclinic, P 21 /c

  • a = 4.2680 (8) Å

  • b = 17.214 (3) Å

  • c = 8.9685 (17) Å

  • β = 100.089 (3)°

  • V = 648.7 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.22 mm−1

  • T = 200 K

  • 0.35 × 0.33 × 0.32 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.220, Tmax = 0.241

  • 3498 measured reflections

  • 1140 independent reflections

  • 965 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.061

  • S = 1.03

  • 1140 reflections

  • 67 parameters

  • H-atom parameters constrained

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Experimental top

Synthesis and crystallization top

Me2NCN (0.76 mL, 9.38 mmol) was added to a solution of (Dipp)N(Li)SiMe3 (0.60 g, 2.35 mmol) in Et2O (30 mL) at -78°C. The resulting mixture was warmed to ca. 25°C and stirred for overnight. The resulting mixture was added dropwise into a suspension of CuBr (0.34 g, 2.35 mmol) in Et2O (10 mL) at -78°C. The resulting mixture was warmed to ca. 25°C and stirred for 24 h, then filtered. The filtrate was concentrated in vacuo and stored at 20°C for ten days, yielding colorless crystals of the title compound (0.503 g, 68%) .

Anal. calcd. for C6H12Br2Li2N4(%): C, 22.96; H, 3.85; N, 17.85. Found: C, 22.93; H, 3.89; N, 17.87. All manipulations were performed under argon using standard Schlenk and vacuum line techniques. Et2O was dried and distilled over Na under argon prior to use. Elemental analysis is completely in agreement with the structure of the compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The methyl H atoms were constrained to an ideal geometry, with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(C).

Comment top

Lithium halidies solvated by Lewis bases have been studied extensively in the past and the various crystal structures exhibit remarkable structural diversity (Snaith et al., 1995; Mulvey, 1991, Gregory et al., 1991). Monomers, dimers, tetra­mers, larger oligomers and polymers are known (Raston, Whitaker & White 1988, 1989a,b; Raston, Skelton et al. 1988; Edwards et al.,1993). Pyridines, chelating amines and Lewis bases containing oxygen usually serve as ligands (Neumann et al., 1995). A 1,3,5,7-tetra­aza­heptatrienyl-lithium salt was reported by W. Marco Boesveld (Boesveld et al., 2009) and we were attempting to synthesize a 1,3,5,7-tetra­aza­heptatrienylcopper complex by the reaction of (Dipp)N(Li)SiMe3 (Dipp = 2,6-diiso­propyl­phenyl), Me2NCN and CuBr. No copper complex was obtained but instead the title polymeric lithium complex (I), (C6H12Br2Li2N4), was isolated from the reaction mixture. Here we present the synthesis and crystal structure of the complex (I).

A low-temperature X-ray crystallographic study shows the basic unit (Fig. 1) of the step structure of complex (I) is centrosymmetric, and to have a polymeric structure (Fig. 2) in the solid state. In the unit, atoms Li1, Br1, Li1A and Br1A are exactly co-planar and constitute a regular rhombic shape [Li—Br—Li 77.55 (16)° and Br—Li—Br 102.45 (16)° ]. The Li1—Br1 and Li1—N1 bond lengths are 2.543 (5) (av.) and 1.999 (5) Å. The bond angles N1—Li1—Br1, N1—Li1—Br1A are 113.1 (2) and 119.6 (2)°, respectively.

Related literature top

For examples of lithium halides solvated by Lewis bases, see: Snaith & Wright (1995); Mulvey (1991); Raston, Skelton et al. (1988), Raston, Whitaker & White (1988, 1989a,b); Edwards et al. (1993); Neumann et al. (1995); Gregory et al. (1991). For related crystal structures, see: Edwards et al. (1993); Raston, Skelton et al. (1988). A 1,3,5,7-tetraazaheptatrienyl–lithium salt was reported by Boesveld et al. (2009).

Structure description top

Lithium halidies solvated by Lewis bases have been studied extensively in the past and the various crystal structures exhibit remarkable structural diversity (Snaith et al., 1995; Mulvey, 1991, Gregory et al., 1991). Monomers, dimers, tetra­mers, larger oligomers and polymers are known (Raston, Whitaker & White 1988, 1989a,b; Raston, Skelton et al. 1988; Edwards et al.,1993). Pyridines, chelating amines and Lewis bases containing oxygen usually serve as ligands (Neumann et al., 1995). A 1,3,5,7-tetra­aza­heptatrienyl-lithium salt was reported by W. Marco Boesveld (Boesveld et al., 2009) and we were attempting to synthesize a 1,3,5,7-tetra­aza­heptatrienylcopper complex by the reaction of (Dipp)N(Li)SiMe3 (Dipp = 2,6-diiso­propyl­phenyl), Me2NCN and CuBr. No copper complex was obtained but instead the title polymeric lithium complex (I), (C6H12Br2Li2N4), was isolated from the reaction mixture. Here we present the synthesis and crystal structure of the complex (I).

A low-temperature X-ray crystallographic study shows the basic unit (Fig. 1) of the step structure of complex (I) is centrosymmetric, and to have a polymeric structure (Fig. 2) in the solid state. In the unit, atoms Li1, Br1, Li1A and Br1A are exactly co-planar and constitute a regular rhombic shape [Li—Br—Li 77.55 (16)° and Br—Li—Br 102.45 (16)° ]. The Li1—Br1 and Li1—N1 bond lengths are 2.543 (5) (av.) and 1.999 (5) Å. The bond angles N1—Li1—Br1, N1—Li1—Br1A are 113.1 (2) and 119.6 (2)°, respectively.

For examples of lithium halides solvated by Lewis bases, see: Snaith & Wright (1995); Mulvey (1991); Raston, Skelton et al. (1988), Raston, Whitaker & White (1988, 1989a,b); Edwards et al. (1993); Neumann et al. (1995); Gregory et al. (1991). For related crystal structures, see: Edwards et al. (1993); Raston, Skelton et al. (1988). A 1,3,5,7-tetraazaheptatrienyl–lithium salt was reported by Boesveld et al. (2009).

Synthesis and crystallization top

Me2NCN (0.76 mL, 9.38 mmol) was added to a solution of (Dipp)N(Li)SiMe3 (0.60 g, 2.35 mmol) in Et2O (30 mL) at -78°C. The resulting mixture was warmed to ca. 25°C and stirred for overnight. The resulting mixture was added dropwise into a suspension of CuBr (0.34 g, 2.35 mmol) in Et2O (10 mL) at -78°C. The resulting mixture was warmed to ca. 25°C and stirred for 24 h, then filtered. The filtrate was concentrated in vacuo and stored at 20°C for ten days, yielding colorless crystals of the title compound (0.503 g, 68%) .

Anal. calcd. for C6H12Br2Li2N4(%): C, 22.96; H, 3.85; N, 17.85. Found: C, 22.93; H, 3.89; N, 17.87. All manipulations were performed under argon using standard Schlenk and vacuum line techniques. Et2O was dried and distilled over Na under argon prior to use. Elemental analysis is completely in agreement with the structure of the compound.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. The methyl H atoms were constrained to an ideal geometry, with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The basic repeat unit of the polymer (I) showing the atom numbering scheme with displacement ellipsoids drawn at the 50% probability level. Atoms labelled with a trailing A are related to the other atoms by the symmetry operation 1-x, 1-y, -z
[Figure 2] Fig. 2. The expanded step polymeric structure of (I) viewed along the crystallographic c axis.
catena-Poly[[(N,N-dimethylcyanamide-κN)lithium]-µ3-bromido] top
Crystal data top
[LiBr(C3H6N2)]F(000) = 304
Mr = 156.85Dx = 1.607 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.2680 (8) ÅCell parameters from 1538 reflections
b = 17.214 (3) Åθ = 2.4–26.5°
c = 8.9685 (17) ŵ = 6.22 mm1
β = 100.089 (3)°T = 200 K
V = 648.7 (2) Å3Block, colourless
Z = 40.35 × 0.33 × 0.32 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
1140 independent reflections
Radiation source: fine-focus sealed tube965 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 53
Tmin = 0.220, Tmax = 0.241k = 2018
3498 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.061 w = 1/[σ2(Fo2) + (0.0285P)2 + 0.3312P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1140 reflectionsΔρmax = 0.57 e Å3
67 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (16)
Crystal data top
[LiBr(C3H6N2)]V = 648.7 (2) Å3
Mr = 156.85Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.2680 (8) ŵ = 6.22 mm1
b = 17.214 (3) ÅT = 200 K
c = 8.9685 (17) Å0.35 × 0.33 × 0.32 mm
β = 100.089 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
1140 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
965 reflections with I > 2σ(I)
Tmin = 0.220, Tmax = 0.241Rint = 0.032
3498 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.061H-atom parameters constrained
S = 1.03Δρmax = 0.57 e Å3
1140 reflectionsΔρmin = 0.38 e Å3
67 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
xyzUiso*/Ueq
Li10.2655 (11)0.4372 (3)0.0594 (6)0.0289 (11)
Br10.81425 (7)0.485193 (18)0.18525 (3)0.03230 (16)
N10.2914 (7)0.32132 (16)0.0517 (3)0.0475 (8)
N20.5102 (8)0.18972 (16)0.0853 (3)0.0509 (8)
C10.3896 (8)0.25987 (19)0.0667 (4)0.0352 (8)
C20.3986 (11)0.1281 (2)0.0201 (5)0.0672 (12)
H2A0.23840.14870.10230.101*
H2B0.30370.08680.03270.101*
H2C0.57790.10700.06210.101*
C30.7254 (9)0.1720 (2)0.2260 (5)0.0581 (11)
H3A0.79970.22060.27750.087*
H3B0.90810.14260.20350.087*
H3C0.61300.14100.29160.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.025 (3)0.022 (3)0.038 (3)0.0034 (19)0.001 (2)0.004 (2)
Br10.0248 (2)0.0371 (2)0.0339 (2)0.00073 (13)0.00223 (13)0.00497 (14)
N10.052 (2)0.0287 (17)0.057 (2)0.0056 (14)0.0034 (15)0.0025 (14)
N20.068 (2)0.0252 (16)0.053 (2)0.0129 (14)0.0071 (16)0.0022 (14)
C10.035 (2)0.032 (2)0.0363 (19)0.0027 (15)0.0003 (14)0.0015 (14)
C20.108 (4)0.036 (2)0.062 (3)0.003 (2)0.027 (2)0.0161 (19)
C30.050 (2)0.058 (3)0.065 (3)0.0178 (19)0.003 (2)0.019 (2)
Geometric parameters (Å, º) top
Li1—N11.999 (5)N2—C11.312 (4)
Li1—Br1i2.535 (5)N2—C21.445 (5)
Li1—Br1ii2.541 (5)N2—C31.457 (5)
Li1—Br12.553 (5)C2—H2A0.9800
Li1—Li1iii3.179 (9)C2—H2B0.9800
Li1—Li1ii3.251 (10)C2—H2C0.9800
Br1—Li1iv2.535 (5)C3—H3A0.9800
Br1—Li1ii2.541 (5)C3—H3B0.9800
N1—C11.137 (4)C3—H3C0.9800
N1—Li1—Br1i113.1 (2)C1—N1—Li1161.0 (3)
N1—Li1—Br1ii119.6 (2)C1—N2—C2121.0 (3)
Br1i—Li1—Br1ii102.45 (16)C1—N2—C3118.4 (3)
N1—Li1—Br1106.6 (2)C2—N2—C3119.9 (3)
Br1i—Li1—Br1114.03 (19)N1—C1—N2178.5 (4)
Br1ii—Li1—Br1100.67 (17)N2—C2—H2A109.5
N1—Li1—Li1iii135.1 (3)N2—C2—H2B109.5
Br1i—Li1—Li1iii51.30 (14)H2A—C2—H2B109.5
Br1ii—Li1—Li1iii51.15 (14)N2—C2—H2C109.5
Br1—Li1—Li1iii118.2 (2)H2A—C2—H2C109.5
N1—Li1—Li1ii127.7 (3)H2B—C2—H2C109.5
Br1i—Li1—Li1ii119.2 (2)N2—C3—H3A109.5
Br1ii—Li1—Li1ii50.50 (13)N2—C3—H3B109.5
Br1—Li1—Li1ii50.17 (13)H3A—C3—H3B109.5
Li1iii—Li1—Li1ii83.2 (2)N2—C3—H3C109.5
Li1iv—Br1—Li1ii77.55 (16)H3A—C3—H3C109.5
Li1iv—Br1—Li1114.03 (19)H3B—C3—H3C109.5
Li1ii—Br1—Li179.33 (17)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula[LiBr(C3H6N2)]
Mr156.85
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)4.2680 (8), 17.214 (3), 8.9685 (17)
β (°) 100.089 (3)
V3)648.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)6.22
Crystal size (mm)0.35 × 0.33 × 0.32
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.220, 0.241
No. of measured, independent and
observed [I > 2σ(I)] reflections
3498, 1140, 965
Rint0.032
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.061, 1.03
No. of reflections1140
No. of parameters67
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.57, 0.38

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge the financial support of the Natural Science Foundation of China (No. 21371111) and Shanxi Scholarship Council of China (No. 2013–025).

References

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages m69-m70
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