Bromidotetra-kis-(1H-2-ethyl-5-methyl-imidazole-κN)copper(II) bromide.

The Cu(II) ion in the title compound, [CuBr(C(6)H(10)N(2))(4)]Br, is coordinated in a square-based-pyramidal geometry by the N atoms of four imidazole ligands and a bromide anion in the apical site. Both the Cu(II) and Br(-) atoms lie on a crystallographic fourfold axis. In the crystal, the [CuBr(C(6)H(10)N(2))(4)](+) complex cations are linked to the uncoordinated Br(-) anions (site symmetry [Formula: see text]) by N-H⋯Br hydrogen bonds, generating a three-dimensional network. The ethyl group of the imidazole ligand was modelled as disordered over two orientations with occupancies of 0.620 (8) and 0.380 (8).

Related literature

For more copper(II) complexes with bromido and imidazole ligands, see: Godlewska et al. (2011 ▶); Hossaini Sadr et al. (2004 ▶); Li et al. (2007 ▶); Liu et al. (2007 ▶); Näther et al. (2002 ▶). For the alignment of dipoles in crystalline materials, see: Anthony & Radhakrishnan (2001 ▶).

Experimental

Crystal data

[CuBr(C6H10N2)4]Br

M = 664

Tetragonal,

a = 14.0961 (4) Å

c = 7.5236 (4) Å

V = 1494.94 (10) Å3

Z = 2

Mo Kα radiation

μ = 3.43 mm−1

T = 294 K

0.54 × 0.45 × 0.33 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2006 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.248, T max = 0.44

5099 measured reflections

1395 independent reflections

898 reflections with I > 2s(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.076

S = 0.95

1395 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051117/hb6533sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051117/hb6533Isup2.hkl

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

[CuBr(C6H10N2)4]Br	Dx = 1.475 Mg m−3
Mr = 664	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/n	Cell parameters from 2155 reflections
Hall symbol: -P 4a	θ = 2.7–28.8°
a = 14.0961 (4) Å	µ = 3.43 mm−1
c = 7.5236 (4) Å	T = 294 K
V = 1494.94 (10) Å3	Prism, blue
Z = 2	0.54 × 0.45 × 0.33 mm
F(000) = 678

Oxford Diffraction Xcalibur Sapphire2 diffractometer	1395 independent reflections
graphite	898 reflections with I > 2s(I)
Detector resolution: 8.1883 pixels mm-1	Rint = 0.025
ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2006), based on expressions derived by Clark & Reid (1995)]	h = −17→10
Tmin = 0.248, Tmax = 0.44	k = −17→15
5099 measured reflections	l = −9→7

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
1395 reflections	(Δ/σ)max = 0.004
103 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. CrysAlisPro (Oxford Diffraction Ltd., 2006) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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	Occ. (<1)
Br1	0.25	0.25	0.31140 (7)	0.0495 (2)
Br2	0.75	0.25	0	0.05286 (19)
Cu1	0.25	0.25	0.67466 (8)	0.0366 (2)
N1	0.22250 (14)	0.39093 (14)	0.6939 (3)	0.0397 (5)
N2	0.21196 (15)	0.54003 (15)	0.7653 (3)	0.0486 (6)
H2	0.2195	0.5922	0.823	0.058*
C1	0.16846 (19)	0.4385 (2)	0.5685 (4)	0.0481 (7)
H1	0.141	0.4104	0.4693	0.058*
C2	0.16140 (19)	0.5299 (2)	0.6100 (4)	0.0520 (8)
C3	0.24764 (19)	0.4552 (2)	0.8122 (4)	0.0446 (7)
C4	0.1150 (3)	0.6113 (2)	0.5178 (5)	0.0900 (14)
H4A	0.0826	0.5888	0.4138	0.135*
H4B	0.1623	0.6568	0.4836	0.135*
H4C	0.0702	0.6408	0.5966	0.135*
C5	0.2915 (9)	0.4385 (17)	0.980 (3)	0.059 (3)	0.620 (8)
H5A	0.2972	0.3709	1.001	0.071*	0.620 (8)
H5B	0.2533	0.4658	1.0744	0.071*	0.620 (8)
C6	0.3952 (5)	0.4870 (5)	0.9776 (9)	0.087 (3)	0.620 (8)
H6A	0.3886	0.5546	0.9672	0.131*	0.620 (8)
H6B	0.4307	0.4632	0.8783	0.131*	0.620 (8)
H6C	0.4279	0.4721	1.0859	0.131*	0.620 (8)
C5A	0.3233 (13)	0.438 (2)	0.966 (4)	0.043 (5)	0.380 (8)
H5A1	0.3232	0.3711	0.9977	0.052*	0.380 (8)
H5A2	0.386	0.4535	0.9218	0.052*	0.380 (8)
C6A	0.3036 (11)	0.4935 (7)	1.1209 (14)	0.123 (6)	0.380 (8)
H6A1	0.3115	0.5595	1.0934	0.184*	0.380 (8)
H6A2	0.3466	0.476	1.2143	0.184*	0.380 (8)
H6A3	0.2395	0.4822	1.1588	0.184*	0.380 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.0587 (3)	0.0587 (3)	0.0311 (3)	0	0	0
Br2	0.0394 (2)	0.0394 (2)	0.0798 (5)	0	0	0
Cu1	0.0350 (2)	0.0350 (2)	0.0397 (4)	0	0	0
N1	0.0396 (13)	0.0367 (12)	0.0428 (14)	0.0018 (10)	−0.0011 (10)	−0.0029 (10)
N2	0.0519 (15)	0.0364 (13)	0.0576 (17)	−0.0021 (11)	0.0071 (13)	−0.0080 (12)
C1	0.0411 (17)	0.0519 (19)	0.0514 (18)	0.0037 (14)	−0.0084 (14)	−0.0031 (15)
C2	0.0455 (18)	0.0466 (19)	0.064 (2)	0.0092 (14)	−0.0011 (16)	0.0027 (16)
C3	0.0485 (18)	0.0436 (17)	0.0418 (17)	−0.0049 (13)	0.0058 (14)	−0.0022 (14)
C4	0.086 (3)	0.058 (2)	0.127 (4)	0.0231 (19)	−0.030 (2)	0.007 (2)
C5	0.060 (9)	0.070 (5)	0.048 (6)	−0.003 (8)	−0.003 (7)	−0.007 (4)
C6	0.104 (6)	0.079 (4)	0.079 (6)	0.010 (4)	−0.047 (4)	−0.021 (3)
C5A	0.038 (11)	0.060 (8)	0.033 (8)	−0.024 (10)	−0.007 (8)	0.007 (6)
C6A	0.252 (18)	0.065 (7)	0.051 (7)	0.045 (8)	−0.051 (9)	−0.023 (6)

Cu1—Br1	2.7330 (8)	C4—H4A	0.96
Cu1—N1i	2.029 (2)	C4—H4B	0.96
Cu1—N1	2.029 (2)	C4—H4C	0.96
Cu1—N1ii	2.029 (2)	C5—C6	1.613 (14)
Cu1—N1iii	2.029 (2)	C5—H5A	0.97
N1—C3	1.319 (3)	C5—H5B	0.97
N1—C1	1.385 (3)	C6—H6A	0.96
N2—C3	1.344 (3)	C6—H6B	0.96
N2—C2	1.376 (4)	C6—H6C	0.96
N2—H2	0.86	C5A—C6A	1.43 (3)
C1—C2	1.330 (4)	C5A—H5A1	0.97
C1—H1	0.93	C5A—H5A2	0.97
C2—C4	1.492 (4)	C6A—H6A1	0.96
C3—C5	1.42 (2)	C6A—H6A2	0.96
C3—C5A	1.59 (3)	C6A—H6A3	0.96
N1i—Cu1—N1	89.708 (9)	N2—C3—C5A	125.4 (12)
N1i—Cu1—N1ii	89.707 (9)	C2—C4—H4A	109.5
N1—Cu1—N1ii	171.81 (12)	C2—C4—H4B	109.5
N1i—Cu1—N1iii	171.81 (12)	H4A—C4—H4B	109.5
N1—Cu1—N1iii	89.707 (9)	C2—C4—H4C	109.5
N1ii—Cu1—N1iii	89.708 (9)	H4A—C4—H4C	109.5
N1i—Cu1—Br1	94.10 (6)	H4B—C4—H4C	109.5
N1—Cu1—Br1	94.10 (6)	C3—C5—C6	108.3 (12)
N1ii—Cu1—Br1	94.10 (6)	C3—C5—H5A	110
N1iii—Cu1—Br1	94.10 (6)	C6—C5—H5A	110
C3—N1—C1	106.0 (2)	C3—C5—H5B	110
C3—N1—Cu1	132.03 (19)	C6—C5—H5B	110
C1—N1—Cu1	122.00 (18)	H5A—C5—H5B	108.4
C3—N2—C2	108.9 (2)	C6A—C5A—C3	112.1 (18)
C3—N2—H2	125.5	C6A—C5A—H5A1	109.2
C2—N2—H2	125.5	C3—C5A—H5A1	109.2
C2—C1—N1	110.5 (3)	C6A—C5A—H5A2	109.2
C2—C1—H1	124.7	C3—C5A—H5A2	109.2
N1—C1—H1	124.7	H5A1—C5A—H5A2	107.9
C1—C2—N2	105.1 (2)	C5A—C6A—H6A1	109.5
C1—C2—C4	132.0 (3)	C5A—C6A—H6A2	109.5
N2—C2—C4	122.8 (3)	H6A1—C6A—H6A2	109.5
N1—C3—N2	109.5 (2)	C5A—C6A—H6A3	109.5
N1—C3—C5	127.0 (10)	H6A1—C6A—H6A3	109.5
N2—C3—C5	122.8 (10)	H6A2—C6A—H6A3	109.5
N1—C3—C5A	124.3 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br2iv	0.86	2.63	3.488 (2)	178

Cu1—Br1	2.7330 (8)
Cu1—N1i	2.029 (2)

N1i—Cu1—N1	89.708 (9)
N1—Cu1—N1ii	171.81 (12)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Br2iii	0.86	2.63	3.488 (2)	178

Symmetry code: (iii) .