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Acta Cryst. (2007). E63, m2437    [ doi:10.1107/S1600536807041700 ]

Dibromidotetrakis(1-vinyl-1H-imidazole-[kappa]N3)copper(II)

F.-Q. Liu, R.-X. Li, S.-X. Li, C.-Q. Li and G.-Y. Liu

Abstract top

In the title compound, [CuBr2(C5H6N2)4], the CuII cation is located on a crystallographic centre of symmetry and coordinated by four N atoms from four 1-vinylimidazole ligands and two trans coordinated Br- anions in a distorted octahedral geometry. In the crystal structure, intra- and intermolecular C-H...Br hydrogen bonds form three-dimensional hydrogen-bond networks which stabilize the structure.

Comment top

In the title compound,(I), The CuII cation is coordinated by four N atoms from four 1-vinylimidazole ligand and two trans coordinated Br− anions in a distorted octahedral geometry (Fig. 1). The equatorial planes are formed by four Cu—N(1-vinylimadazole) bonds [Cu—N2 = 2.007 (6) Å, Cu—N4 = 2.029 (6) Å] and the axial positions are occupied by two Br− ions [Cu—Br = 3.0340 (11) Å]. The Cu—N bond lengths agree well with those observed in [Cu(imidazole)Br2] (Parker & Breneman, 1995), but the Cu—Br bond length is shorter than that in [Cu(imidazole)Br2]. In the crystal, the intramolecular and intermolecular C—H···Br hydrogen bonds form three-dimensional hydrogen bond networks to stabilize the structure.

Related literature top

For related literature, see: Parker & Breneman (1995).

Experimental top

The title compound was prepared by the reaction of 1-vinylimidazole (0.47 g, 5 mmol) with CuBr2 (0.72 g, 5 mmol) by means of hydrothermal synthesis in a stainless-steel reactor with a Teflon liner at 383 K for 24 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

H atoms were positioned geometrically (C—H = 0.93 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme [symmetry code: (A):-x + 1,-y + 1,-z + 1].
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis.
Dibromidotetrakis(1-vinyl-1H-imidazole-κN3)copper(II) top
Crystal data top
[CuBr2(C5H6N2)4]F000 = 598
Mr = 599.82Dx = 1.614 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2268 reflections
a = 7.7280 (15) Åθ = 4–15º
b = 15.144 (3) ŵ = 4.15 mm−1
c = 11.039 (2) ÅT = 293 (2) K
β = 107.23 (3)ºBlock, blue
V = 1234.0 (5) Å30.40 × 0.10 × 0.10 mm
Z = 2
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2416 independent reflections
Radiation source: fine-focus sealed tube1446 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.013
T = 293(2) Kθmax = 26.0º
Thin–slice ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −9→9
Tmin = 0.605, Tmax = 0.659k = 0→18
2568 measured reflectionsl = 0→13
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)] = 0.065H-atom parameters constrained
wR(F2) = 0.164  w = 1/[σ2(Fo2) + (0.07P)2 + P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2416 reflectionsΔρmax = 0.82 e Å−3
124 parametersΔρmin = −0.84 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[CuBr2(C5H6N2)4]V = 1234.0 (5) Å3
Mr = 599.82Z = 2
Monoclinic, P21/nMo Kα
a = 7.7280 (15) ŵ = 4.15 mm−1
b = 15.144 (3) ÅT = 293 (2) K
c = 11.039 (2) Å0.40 × 0.10 × 0.10 mm
β = 107.23 (3)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2416 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1446 reflections with I > 2σ(I)
Tmin = 0.605, Tmax = 0.659Rint = 0.013
2568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0652 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.03Δρmax = 0.82 e Å−3
2416 reflectionsΔρmin = −0.84 e Å−3
124 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
Br0.17188 (11)0.38082 (6)0.45787 (8)0.054
Cu0.50000.50000.50000.0477 (4)
N10.3333 (10)0.5776 (5)0.8077 (7)0.0598 (19)
N20.4621 (8)0.5408 (4)0.6632 (6)0.0460 (16)
N30.0973 (9)0.6672 (4)0.2833 (7)0.0514 (17)
N40.3382 (8)0.5963 (4)0.3984 (6)0.0452 (16)
C10.1989 (17)0.6136 (7)0.9774 (11)0.100
H1A0.31350.61201.03610.120*
H1B0.09800.62621.00390.120*
C20.1776 (18)0.5966 (8)0.8455 (11)0.104
H2A0.06350.59810.78610.125*
C30.3085 (11)0.5535 (5)0.6875 (8)0.053 (2)
H3A0.19540.54660.62820.064*
C40.5950 (13)0.5582 (7)0.7757 (9)0.066 (3)
H4A0.71930.55560.78800.079*
C50.5153 (15)0.5795 (7)0.8639 (9)0.076 (3)
H5A0.57380.59310.94830.091*
C6−0.1584 (14)0.7383 (7)0.1260 (10)0.089 (3)
H6A−0.07960.76190.08510.106*
H6B−0.28200.74970.09520.106*
C7−0.0897 (13)0.6847 (6)0.2360 (8)0.072 (3)
H7A−0.16870.66120.27670.086*
C80.2447 (13)0.7082 (6)0.2648 (8)0.060 (2)
H8A0.24340.75730.21400.072*
C90.3952 (12)0.6632 (6)0.3353 (8)0.059 (2)
H9A0.51470.67580.33960.071*
C100.1625 (11)0.6012 (5)0.3668 (8)0.052 (2)
H10A0.09020.56380.39800.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0540.0540.0540.0000.0160.000
Cu0.0553 (8)0.0510 (8)0.0381 (8)0.0152 (7)0.0157 (6)0.0062 (7)
N10.071 (5)0.066 (5)0.050 (5)0.006 (4)0.029 (4)−0.002 (4)
N20.039 (3)0.052 (4)0.046 (4)0.009 (3)0.012 (3)0.003 (3)
N30.060 (4)0.041 (4)0.052 (4)0.008 (3)0.014 (3)0.009 (3)
N40.050 (4)0.047 (4)0.040 (4)0.007 (3)0.015 (3)0.010 (3)
C10.1000.1000.1000.0000.0300.000
C20.1040.1040.1040.0000.0310.000
C30.056 (5)0.049 (5)0.056 (6)0.001 (4)0.018 (4)−0.002 (4)
C40.063 (6)0.086 (7)0.049 (6)0.007 (5)0.018 (5)−0.010 (5)
C50.093 (8)0.076 (7)0.048 (6)0.007 (6)0.007 (6)−0.004 (5)
C60.076 (7)0.085 (8)0.090 (8)0.018 (6)0.002 (6)0.024 (7)
C70.068 (6)0.074 (7)0.065 (7)0.019 (5)0.008 (5)0.000 (5)
C80.083 (6)0.043 (5)0.056 (6)0.016 (5)0.021 (5)0.011 (4)
C90.063 (5)0.061 (6)0.060 (6)0.005 (5)0.027 (5)0.013 (5)
C100.055 (5)0.036 (5)0.068 (6)0.007 (4)0.024 (4)0.008 (4)
Geometric parameters (Å, °) top
Cu—Br3.0340 (11)C1—H1A0.9300
Cu—N22.007 (6)C1—H1B0.9300
Cu—N2i2.007 (6)C2—H2A0.9300
Cu—N4i2.029 (6)C3—H3A0.9300
Cu—N42.029 (6)C4—C51.336 (13)
N1—C31.334 (10)C4—H4A0.9300
N1—C51.359 (12)C5—H5A0.9300
N1—C21.414 (13)C6—C71.427 (8)
N2—C31.306 (9)C6—H6A0.9300
N2—C41.383 (11)C6—H6B0.9300
N3—C101.351 (10)C7—H7A0.9300
N3—C81.365 (11)C8—C91.374 (12)
N3—C71.408 (10)C8—H8A0.9300
N4—C101.301 (10)C9—H9A0.9300
N4—C91.373 (10)C10—H10A0.9300
C1—C21.439 (9)
N2—Cu—N2i180.000 (1)N2—C3—N1111.9 (8)
N2—Cu—N4i87.4 (2)N2—C3—H3A124.0
N2i—Cu—N4i92.6 (2)N1—C3—H3A124.0
N2—Cu—N492.6 (2)C5—C4—N2108.6 (9)
N2i—Cu—N487.4 (2)C5—C4—H4A125.7
N4i—Cu—N4180.000 (1)N2—C4—H4A125.7
C3—N1—C5106.5 (8)C4—C5—N1107.5 (9)
C3—N1—C2117.7 (9)C4—C5—H5A126.2
C5—N1—C2135.8 (9)N1—C5—H5A126.2
C3—N2—C4105.4 (7)C7—C6—H6A120.0
C3—N2—Cu127.8 (6)C7—C6—H6B120.0
C4—N2—Cu126.7 (5)H6A—C6—H6B120.0
C10—N3—C8106.2 (7)N3—C7—C6120.3 (9)
C10—N3—C7121.8 (7)N3—C7—H7A119.8
C8—N3—C7132.0 (7)C6—C7—H7A119.8
C10—N4—C9106.7 (7)N3—C8—C9107.1 (7)
C10—N4—Cu127.8 (5)N3—C8—H8A126.5
C9—N4—Cu124.9 (5)C9—C8—H8A126.5
C2—C1—H1A120.0N4—C9—C8108.0 (8)
C2—C1—H1B120.0N4—C9—H9A126.0
H1A—C1—H1B120.0C8—C9—H9A126.0
N1—C2—C1118.8 (11)N4—C10—N3112.0 (7)
N1—C2—H2A120.6N4—C10—H10A124.0
C1—C2—H2A120.6N3—C10—H10A124.0
N4i—Cu—N2—C3−126.5 (7)Cu—N2—C4—C5−176.9 (6)
N4—Cu—N2—C353.5 (7)N2—C4—C5—N1−1.3 (12)
N4i—Cu—N2—C451.0 (7)C3—N1—C5—C41.2 (11)
N4—Cu—N2—C4−129.0 (7)C2—N1—C5—C4−176.8 (11)
N2—Cu—N4—C10−73.6 (7)C10—N3—C7—C6−164.0 (9)
N2i—Cu—N4—C10106.4 (7)C8—N3—C7—C618.7 (15)
N2—Cu—N4—C9115.8 (7)C10—N3—C8—C92.0 (10)
N2i—Cu—N4—C9−64.2 (7)C7—N3—C8—C9179.6 (9)
C3—N1—C2—C1173.5 (10)C10—N4—C9—C80.0 (10)
C5—N1—C2—C1−8.7 (19)Cu—N4—C9—C8172.3 (6)
C4—N2—C3—N1−0.2 (10)N3—C8—C9—N4−1.3 (10)
Cu—N2—C3—N1177.6 (5)C9—N4—C10—N31.3 (10)
C5—N1—C3—N2−0.6 (10)Cu—N4—C10—N3−170.7 (5)
C2—N1—C3—N2177.8 (8)C8—N3—C10—N4−2.1 (10)
C3—N2—C4—C51.0 (11)C7—N3—C10—N4−180.0 (7)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Brii0.932.793.643 (12)154
C3—H3A···Brii0.932.933.717 (9)144
C8—H8A···Briii0.932.873.772 (9)163
C10—H10A···Br0.932.883.480 (8)124
Symmetry codes: (ii) −x, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Bri0.932.793.643 (12)154
C3—H3A···Bri0.932.933.717 (9)144
C8—H8A···Brii0.932.873.772 (9)163
C10—H10A···Br0.932.883.480 (8)124
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+1/2.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (grant No. Y2006B12).

references
References top

Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.

Parker, O. J. & Breneman, G. L. (1995). Acta Cryst. C51, 1097–1099.

Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.