Bis[2-(1H-benzotriazol-1-yl)acetonitrile-κN]dibromidocopper(II).

In the title complex, [CuBr(2)(C(8)H(6)N(4))(2)], the Cu(II) atom is located on an inversion centre and the asymmetric unit comprises one half-mol-ecule. The Cu atom is coordinated by two Br ions and two N atoms in approximately square-planar geometry. In the crystal structure, inter-molecular C-H⋯Br hydrogen bonds and π-π inter-actions between benzotriazole rings (centroid-centroid distance = 3.651 Å) generate a three-dimensional network.

Related literature

For the synthesis of the organic ligand, see: Danan et al. (1997 ▶); Xu & Ye (2007 ▶). For the structure of a similar complex, see: Hang & Ye (2008 ▶).

Experimental

Crystal data

[CuBr2(C8H6N4)2]

M = 539.70

Triclinic,

a = 7.9034 (16) Å

b = 8.1434 (16) Å

c = 8.7849 (18) Å

α = 116.04 (3)°

β = 105.86 (3)°

γ = 100.74 (3)°

V = 456.9 (3) Å3

Z = 1

Mo Kα radiation

μ = 5.59 mm−1

T = 293 (2) K

0.20 × 0.12 × 0.12 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.702, T max = 1.000 (expected range = 0.359–0.511)

4726 measured reflections

2095 independent reflections

1809 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.218

S = 1.06

2095 reflections

124 parameters

H-atom parameters constrained

Δρmax = 3.13 e Å−3

Δρmin = −1.39 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019260/kp2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019260/kp2178Isup2.hkl

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

[CuBr2(C8H6N4)2]	Z = 1
Mr = 539.70	F000 = 263
Triclinic, P1	Dx = 1.961 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.9034 (16) Å	Cell parameters from 4665 reflections
b = 8.1434 (16) Å	θ = 6.2–57.6º
c = 8.7849 (18) Å	µ = 5.59 mm−1
α = 116.04 (3)º	T = 293 (2) K
β = 105.86 (3)º	Block, red
γ = 100.74 (3)º	0.20 × 0.12 × 0.12 mm
V = 456.9 (3) Å3

Rigaku Mercury2 diffractometer	2095 independent reflections
Radiation source: fine-focus sealed tube	1809 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.702, Tmax = 1.000	l = −11→11
4726 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.218	w = 1/[σ2(Fo2) + (0.1128P)2 + 5.2279P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2095 reflections	Δρmax = 3.13 e Å−3
124 parameters	Δρmin = −1.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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	0.13948 (13)	−0.20325 (12)	0.56625 (11)	0.0403 (3)
Cu1	0.0000	0.0000	0.5000	0.0170 (3)
C8	−0.2130 (9)	−0.4022 (9)	0.1349 (8)	0.0175 (12)
N4	−0.0651 (9)	−0.1575 (8)	0.1166 (7)	0.0240 (12)
N3	−0.1103 (9)	−0.2050 (8)	0.2291 (7)	0.0222 (12)
N2	−0.3749 (15)	−0.2480 (17)	−0.3869 (13)	0.065 (3)
C7	−0.1043 (11)	−0.3097 (11)	−0.2015 (9)	0.0242 (14)
H7A	−0.0935	−0.4308	−0.2836	0.029*
H7B	0.0128	−0.2042	−0.1526	0.029*
C6	−0.3269 (10)	−0.6762 (10)	−0.1849 (9)	0.0258 (14)
H6A	−0.3384	−0.7258	−0.3064	0.031*
N1	−0.1353 (8)	−0.3207 (8)	−0.0490 (7)	0.0210 (11)
C5	−0.2293 (9)	−0.4777 (9)	−0.0471 (8)	0.0181 (12)
C4	−0.4036 (11)	−0.7908 (11)	−0.1270 (11)	0.0316 (16)
H4A	−0.4675	−0.9237	−0.2119	0.038*
C3	−0.2596 (12)	−0.2759 (12)	−0.3062 (10)	0.0325 (17)
C2	−0.3899 (11)	−0.7159 (11)	0.0551 (11)	0.0297 (15)
H2A	−0.4465	−0.8002	0.0862	0.036*
C1	−0.2947 (10)	−0.5205 (10)	0.1897 (9)	0.0239 (13)
H1A	−0.2860	−0.4712	0.3103	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.0515 (6)	0.0375 (5)	0.0321 (5)	0.0196 (4)	0.0162 (4)	0.0169 (4)
Cu1	0.0271 (6)	0.0117 (5)	0.0069 (5)	0.0051 (4)	0.0055 (4)	0.0022 (4)
C8	0.025 (3)	0.015 (3)	0.008 (3)	0.008 (2)	0.003 (2)	0.003 (2)
N4	0.038 (3)	0.017 (3)	0.011 (2)	0.008 (2)	0.008 (2)	0.005 (2)
N3	0.038 (3)	0.015 (3)	0.011 (2)	0.007 (2)	0.008 (2)	0.006 (2)
N2	0.075 (7)	0.088 (8)	0.037 (5)	0.052 (6)	0.018 (4)	0.031 (5)
C7	0.039 (4)	0.027 (3)	0.017 (3)	0.016 (3)	0.018 (3)	0.014 (3)
C6	0.029 (3)	0.020 (3)	0.012 (3)	0.009 (3)	0.004 (3)	−0.002 (2)
N1	0.035 (3)	0.017 (2)	0.010 (2)	0.010 (2)	0.009 (2)	0.006 (2)
C5	0.021 (3)	0.019 (3)	0.013 (3)	0.009 (2)	0.006 (2)	0.008 (2)
C4	0.030 (4)	0.017 (3)	0.032 (4)	0.004 (3)	0.006 (3)	0.005 (3)
C3	0.049 (5)	0.037 (4)	0.014 (3)	0.021 (4)	0.015 (3)	0.013 (3)
C2	0.028 (3)	0.024 (4)	0.033 (4)	0.006 (3)	0.010 (3)	0.015 (3)
C1	0.029 (3)	0.024 (3)	0.018 (3)	0.010 (3)	0.009 (3)	0.010 (3)

Br1—Cu1	2.3385 (10)	C7—H7B	0.9700
Cu1—N3	2.012 (5)	C6—C4	1.368 (11)
C8—N3	1.379 (8)	C6—C5	1.407 (9)
C8—C1	1.387 (9)	C6—H6A	0.9300
C8—C5	1.395 (8)	N1—C5	1.363 (9)
N4—N3	1.316 (8)	C4—C2	1.402 (11)
N4—N1	1.333 (7)	C4—H4A	0.9300
N2—C3	1.118 (12)	C2—C1	1.383 (10)
C7—N1	1.462 (8)	C2—H2A	0.9300
C7—C3	1.470 (10)	C1—H1A	0.9300
C7—H7A	0.9700
N3—Cu1—Br1	89.46 (16)	N4—N1—C5	111.7 (5)
N3—C8—C1	132.2 (6)	N4—N1—C7	118.6 (6)
N3—C8—C5	106.6 (6)	C5—N1—C7	129.7 (6)
C1—C8—C5	121.2 (6)	N1—C5—C8	104.5 (5)
N3—N4—N1	107.1 (5)	N1—C5—C6	132.8 (6)
N4—N3—C8	110.1 (5)	C8—C5—C6	122.7 (6)
N4—N3—Cu1	118.1 (4)	C6—C4—C2	122.7 (7)
C8—N3—Cu1	131.4 (4)	C6—C4—H4A	118.7
N1—C7—C3	111.1 (6)	C2—C4—H4A	118.7
N1—C7—H7A	109.4	N2—C3—C7	178.4 (10)
C3—C7—H7A	109.4	C1—C2—C4	122.0 (7)
N1—C7—H7B	109.4	C1—C2—H2A	119.0
C3—C7—H7B	109.4	C4—C2—H2A	119.0
H7A—C7—H7B	108.0	C2—C1—C8	116.3 (6)
C4—C6—C5	115.1 (6)	C2—C1—H1A	121.9
C4—C6—H6A	122.5	C8—C1—H1A	121.9
C5—C6—H6A	122.5
N1—N4—N3—C8	−0.5 (8)	N4—N1—C5—C8	−0.4 (7)
N1—N4—N3—Cu1	172.6 (4)	C7—N1—C5—C8	179.9 (7)
C1—C8—N3—N4	−178.7 (7)	N4—N1—C5—C6	179.3 (7)
C5—C8—N3—N4	0.3 (8)	C7—N1—C5—C6	−0.5 (12)
C1—C8—N3—Cu1	9.4 (11)	N3—C8—C5—N1	0.0 (7)
C5—C8—N3—Cu1	−171.6 (5)	C1—C8—C5—N1	179.2 (6)
N3i—Cu1—N3—N4	−167 (92)	N3—C8—C5—C6	−179.7 (6)
Br1i—Cu1—N3—N4	59.4 (5)	C1—C8—C5—C6	−0.6 (10)
Br1—Cu1—N3—N4	−120.6 (5)	C4—C6—C5—N1	179.8 (7)
N3i—Cu1—N3—C8	4(93)	C4—C6—C5—C8	−0.5 (10)
Br1i—Cu1—N3—C8	−129.2 (6)	C5—C6—C4—C2	1.3 (11)
Br1—Cu1—N3—C8	50.8 (6)	N1—C7—C3—N2	150 (33)
N3—N4—N1—C5	0.5 (8)	C6—C4—C2—C1	−1.0 (12)
N3—N4—N1—C7	−179.7 (6)	C4—C2—C1—C8	−0.1 (11)
C3—C7—N1—N4	−91.8 (8)	N3—C8—C1—C2	179.7 (7)
C3—C7—N1—C5	87.9 (9)	C5—C8—C1—C2	0.9 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Br1ii	0.97	2.79	3.744 (7)	168
C7—H7B···Br1iii	0.97	2.91	3.421 (7)	114

Br1—Cu1	2.3385 (10)
Cu1—N3	2.012 (5)

N3—Cu1—Br1

89.46 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Br1i	0.97	2.79	3.744 (7)	168
C7—H7B⋯Br1ii	0.97	2.91	3.421 (7)	114

Symmetry codes: (i) ; (ii) .