Bis[μ-2-(pyridin-2-yl)ethano-lato]bis-[bromidocopper(II)].

The title compound, [Cu(2)Br(2)(C(7)H(8)NO)(2)], was synthesized by reaction of CuBr(2) with 2-(pyridin-2-yl)ethanol (hep-H) in methanol. The asymmetric unit consists of one hep ligand and a CuBr unit. The Cu(2+) ion is thereby coordinated by the N atom and the deprotonated hydroxy O atom in a distorted square-planar geometry that is completed by another O atom. The latter acts as bridging ligand towards the second, symmetry-equivalent, Cu atom, thus generating a centrosymmetric dimeric unit, with the inversion centre halfway between the Cu atoms. These units are linked via C-H⋯Br and C-H⋯O hydrogen bonds, leading to the formation of a hydrogen-bonded one-dimensional-polymeric chain along a..

Related literature

For similar dinuclear copper complexes see Lah et al. (2006 ▶); Shaikh et al. (2010 ▶).

Experimental

Crystal data

[Cu2Br2(C7H8NO)2]

M = 531.19

Triclinic,

a = 4.2066 (2) Å

b = 8.4338 (3) Å

c = 11.5113 (6) Å

α = 91.122 (4)°

β = 90.195 (3)°

γ = 97.033 (1)°

V = 405.24 (3) Å3

Z = 1

Mo Kα radiation

μ = 7.56 mm−1

T = 150 K

0.28 × 0.21 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶)T min = 0.226, T max = 0.360

3453 measured reflections

1388 independent reflections

1298 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.087

S = 1.05

1388 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.74 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043637/fi2115sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043637/fi2115Isup2.hkl

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

[Cu2Br2(C7H8NO)2]	Z = 1
Mr = 531.19	F(000) = 258
Triclinic, P1	Dx = 2.177 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.2066 (2) Å	Cell parameters from 3586 reflections
b = 8.4338 (3) Å	θ = 3.5–30.0°
c = 11.5113 (6) Å	µ = 7.56 mm−1
α = 91.122 (4)°	T = 150 K
β = 90.195 (3)°	Block, blue
γ = 97.033 (1)°	0.28 × 0.21 × 0.17 mm
V = 405.24 (3) Å3

Oxford Diffraction Xcalibur-S diffractometer	1388 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1298 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 15.9948 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω/q scans	h = −5→4
Absorption correction: multi-scan (CrysAlis PRO-RED; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.226, Tmax = 0.360	l = −13→13
3453 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.5089P] where P = (Fo2 + 2Fc2)/3
1388 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cu1	0.91306 (11)	0.96968 (5)	0.87303 (4)	0.01736 (18)
Br1	0.60658 (9)	0.76112 (4)	0.76674 (3)	0.02191 (18)
O1	1.0535 (7)	1.1399 (3)	0.9846 (2)	0.0219 (6)
N1	1.0035 (8)	1.1189 (4)	0.7436 (3)	0.0174 (7)
C1	1.1498 (10)	1.0720 (5)	0.6475 (4)	0.0220 (9)
H1	1.1873	0.9635	0.6396	0.026*
C2	1.2475 (10)	1.1759 (5)	0.5598 (4)	0.0254 (9)
H2	1.3495	1.1398	0.4925	0.030*
C3	1.1933 (10)	1.3341 (5)	0.5722 (4)	0.0266 (10)
H3	1.2575	1.4082	0.5131	0.032*
C4	1.0444 (10)	1.3833 (5)	0.6716 (4)	0.0226 (9)
H4	1.0082	1.4917	0.6817	0.027*
C5	0.9486 (9)	1.2720 (5)	0.7564 (3)	0.0186 (8)
C6	0.7862 (9)	1.3159 (5)	0.8657 (4)	0.0197 (8)
H6A	0.5811	1.2456	0.8729	0.024*
H6B	0.7365	1.4273	0.8605	0.024*
C7	0.9894 (10)	1.3012 (4)	0.9745 (3)	0.0195 (8)
H7A	1.1934	1.3728	0.9691	0.023*
H7B	0.8737	1.3335	1.0441	0.023*

	U11	U22	U33	U12	U13	U23
Cu1	0.0243 (3)	0.0158 (3)	0.0116 (3)	0.0008 (2)	0.0009 (2)	0.0016 (2)
Br1	0.0253 (3)	0.0211 (3)	0.0183 (3)	−0.00140 (17)	−0.00193 (18)	0.00043 (17)
O1	0.0347 (17)	0.0151 (14)	0.0161 (15)	0.0033 (12)	−0.0002 (12)	0.0032 (11)
N1	0.0201 (17)	0.0206 (17)	0.0117 (17)	0.0031 (13)	−0.0019 (13)	0.0001 (13)
C1	0.025 (2)	0.024 (2)	0.018 (2)	0.0060 (16)	0.0004 (17)	0.0012 (17)
C2	0.025 (2)	0.035 (2)	0.016 (2)	0.0017 (18)	0.0049 (17)	−0.0003 (18)
C3	0.028 (2)	0.029 (2)	0.022 (2)	−0.0008 (18)	0.0017 (18)	0.0086 (18)
C4	0.027 (2)	0.019 (2)	0.021 (2)	−0.0008 (16)	−0.0011 (17)	0.0030 (16)
C5	0.0153 (19)	0.023 (2)	0.018 (2)	0.0019 (15)	−0.0031 (15)	0.0012 (16)
C6	0.020 (2)	0.0186 (19)	0.021 (2)	0.0043 (16)	0.0010 (16)	0.0007 (16)
C7	0.023 (2)	0.0172 (19)	0.018 (2)	0.0034 (15)	0.0048 (16)	0.0000 (16)

Cu1—O1i	1.910 (3)	C2—H2	0.9500
Cu1—O1	1.943 (3)	C3—C4	1.387 (6)
Cu1—N1	1.977 (3)	C3—H3	0.9500
Cu1—Br1	2.3670 (6)	C4—C5	1.394 (6)
Cu1—Cu1i	3.0294 (9)	C4—H4	0.9500
O1—C7	1.426 (4)	C5—C6	1.496 (6)
O1—Cu1i	1.910 (3)	C6—C7	1.529 (6)
N1—C5	1.344 (5)	C6—H6A	0.9900
N1—C1	1.344 (5)	C6—H6B	0.9900
C1—C2	1.380 (6)	C7—H7A	0.9900
C1—H1	0.9500	C7—H7B	0.9900
C2—C3	1.385 (6)
O1i—Cu1—O1	76.32 (12)	C2—C3—C4	119.4 (4)
O1i—Cu1—N1	162.34 (14)	C2—C3—H3	120.3
O1—Cu1—N1	90.44 (12)	C4—C3—H3	120.3
O1i—Cu1—Br1	98.08 (8)	C3—C4—C5	119.3 (4)
O1—Cu1—Br1	163.87 (9)	C3—C4—H4	120.4
N1—Cu1—Br1	97.69 (10)	C5—C4—H4	120.4
O1i—Cu1—Cu1i	38.54 (8)	N1—C5—C4	120.8 (4)
O1—Cu1—Cu1i	37.78 (8)	N1—C5—C6	116.9 (3)
N1—Cu1—Cu1i	127.28 (10)	C4—C5—C6	122.4 (4)
Br1—Cu1—Cu1i	134.80 (3)	C5—C6—C7	112.9 (3)
C7—O1—Cu1i	125.6 (2)	C5—C6—H6A	109.0
C7—O1—Cu1	124.4 (2)	C7—C6—H6A	109.0
Cu1i—O1—Cu1	103.68 (12)	C5—C6—H6B	109.0
C5—N1—C1	119.7 (3)	C7—C6—H6B	109.0
C5—N1—Cu1	119.9 (3)	H6A—C6—H6B	107.8
C1—N1—Cu1	120.0 (3)	O1—C7—C6	109.4 (3)
N1—C1—C2	122.3 (4)	O1—C7—H7A	109.8
N1—C1—H1	118.9	C6—C7—H7A	109.8
C2—C1—H1	118.9	O1—C7—H7B	109.8
C1—C2—C3	118.5 (4)	C6—C7—H7B	109.8
C1—C2—H2	120.8	H7A—C7—H7B	108.2
C3—C2—H2	120.8
O1i—Cu1—O1—C7	−153.1 (4)	Cu1—N1—C1—C2	−173.3 (3)
N1—Cu1—O1—C7	38.7 (3)	N1—C1—C2—C3	0.3 (6)
Br1—Cu1—O1—C7	−81.8 (4)	C1—C2—C3—C4	0.2 (6)
Cu1i—Cu1—O1—C7	−153.1 (4)	C2—C3—C4—C5	−0.8 (6)
O1i—Cu1—O1—Cu1i	0.0	C1—N1—C5—C4	−0.6 (6)
N1—Cu1—O1—Cu1i	−168.20 (15)	Cu1—N1—C5—C4	172.6 (3)
Br1—Cu1—O1—Cu1i	71.3 (3)	C1—N1—C5—C6	−179.7 (4)
O1i—Cu1—N1—C5	−77.1 (5)	Cu1—N1—C5—C6	−6.5 (5)
O1—Cu1—N1—C5	−36.2 (3)	C3—C4—C5—N1	1.1 (6)
Br1—Cu1—N1—C5	129.8 (3)	C3—C4—C5—C6	−179.9 (4)
Cu1i—Cu1—N1—C5	−45.2 (3)	N1—C5—C6—C7	65.4 (5)
O1i—Cu1—N1—C1	96.1 (5)	C4—C5—C6—C7	−113.7 (4)
O1—Cu1—N1—C1	137.0 (3)	Cu1i—O1—C7—C6	−145.3 (3)
Br1—Cu1—N1—C1	−56.9 (3)	Cu1—O1—C7—C6	1.9 (4)
Cu1i—Cu1—N1—C1	128.0 (3)	C5—C6—C7—O1	−60.6 (4)
C5—N1—C1—C2	−0.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1ii	0.95	3.00	3.716 (4)	134.
C6—H6A···O1iii	0.99	2.64	3.545 (5)	153.

Cu1—O1i	1.910 (3)
Cu1—O1	1.943 (3)
Cu1—N1	1.977 (3)
Cu1—Br1	2.3670 (6)
Cu1—Cu1i	3.0294 (9)

O1i—Cu1—O1	76.32 (12)
Cu1i—O1—Cu1	103.68 (12)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1ii	0.95	3.00	3.716 (4)	134
C6—H6A⋯O1iii	0.99	2.64	3.545 (5)	153

Symmetry codes: (ii) ; (iii) .