Di-μ-chlorido-bis-{[2-(2-pyridylmethyl-amino)ethanesulfonato-κN,N',O]copper(II)}.

In the title compound, [Cu(2)(C(8)H(11)N(2)O(3)S)(2)Cl(2)], the Cu atoms are five-coordinated in a distorted square-pyramidal geometry by three donor atoms of the deprotonated anionic 2-(2-pyridylmethyl-amino)ethanesulfonate (pmt) ligand and two Cl atoms. The Cl atoms bridge two Cu atoms, giving a binuclear structure; the centroid of the Cu(2)Cl(2) ring lies on a crystallographic center of inversion. The complex is stabilized by hydrogen bonds and π-π stacking inter-actions [average inter-planar distance = 3.4969 (1) Å and ring-centroid separation distance = 4.1068 (4) Å].

Related literature

For related literature, see: Li et al. (2006 ▶, 2007a ▶,b ▶).

Experimental

Crystal data

[Cu2(C8H11N2O3S)2Cl2]

M = 628.48

Triclinic,

a = 8.294 (1) Å

b = 8.362 (1) Å

c = 9.110 (1) Å

α = 103.773 (2)°

β = 98.118 (2)°

γ = 113.043 (2)°

V = 544.9 (1) Å3

Z = 1

Mo Kα radiation

μ = 2.43 mm−1

T = 291 (2) K

0.33 × 0.20 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.504, T max = 0.811

3270 measured reflections

2385 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.067

S = 1.10

2385 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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 global, I. DOI: 10.1107/S1600536808000779/im2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000779/im2051Isup2.hkl

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

[Cu2(C8H11N2O3S)2Cl2]	Z = 1
Mr = 628.28	F000 = 318
Triclinic, P1	Dx = 1.915 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.294 (1) Å	Cell parameters from 2667 reflections
b = 8.362 (1) Å	θ = 2.4–28.3º
c = 9.110 (1) Å	µ = 2.43 mm−1
α = 103.773 (2)º	T = 291 (2) K
β = 98.118 (2)º	Block, blue
γ = 113.043 (2)º	0.33 × 0.20 × 0.09 mm
V = 544.9 (1) Å3

Bruker APEXII CCD area-detector diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.009
T = 291(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.505, Tmax = 0.811	k = −10→10
3270 measured reflections	l = −9→11

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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.037P)2 + 0.2091P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2385 reflections	Δρmax = 0.48 e Å−3
149 parameters	Δρmin = −0.34 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
Cu1	−0.00815 (3)	0.79189 (3)	0.40050 (2)	0.02480 (9)
Cl1	0.21525 (6)	1.15056 (7)	0.48221 (5)	0.02695 (12)
S1	0.25729 (6)	0.72960 (7)	0.64825 (6)	0.02540 (12)
O1	0.09412 (19)	0.7556 (2)	0.59265 (16)	0.0311 (3)
O2	0.4160 (2)	0.9013 (2)	0.72554 (19)	0.0385 (4)
O3	0.2140 (2)	0.6050 (2)	0.74013 (19)	0.0381 (4)
N1	−0.1223 (2)	0.7825 (2)	0.18742 (18)	0.0257 (3)
N2	0.1380 (2)	0.6952 (2)	0.2771 (2)	0.0276 (3)
C1	−0.2789 (3)	0.7931 (4)	0.1445 (3)	0.0382 (5)
H1	−0.3426	0.8078	0.2188	0.046*
C2	−0.3480 (3)	0.7828 (4)	−0.0065 (3)	0.0443 (6)
H2	−0.4578	0.7878	−0.0340	0.053*
C3	−0.2519 (3)	0.7652 (3)	−0.1151 (2)	0.0391 (5)
H3	−0.2961	0.7581	−0.2174	0.047*
C4	−0.0881 (3)	0.7580 (3)	−0.0712 (2)	0.0332 (5)
H4	−0.0203	0.7481	−0.1430	0.040*
C5	−0.0275 (3)	0.7659 (3)	0.0813 (2)	0.0264 (4)
C6	0.1491 (3)	0.7631 (3)	0.1417 (2)	0.0314 (4)
H6A	0.1726	0.6835	0.0600	0.038*
H6B	0.2478	0.8857	0.1731	0.038*
C7	0.3187 (3)	0.7178 (3)	0.3579 (2)	0.0287 (4)
H7A	0.3988	0.8472	0.4099	0.034*
H7B	0.3725	0.6699	0.2812	0.034*
C8	0.2998 (3)	0.6170 (3)	0.4776 (2)	0.0296 (4)
H8A	0.4104	0.6049	0.5074	0.035*
H8B	0.2011	0.4944	0.4297	0.035*
H1N	0.051 (4)	0.570 (4)	0.233 (3)	0.045 (7)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02148 (14)	0.03819 (16)	0.02055 (13)	0.01626 (11)	0.00702 (9)	0.01323 (10)
Cl1	0.0222 (2)	0.0363 (3)	0.0269 (2)	0.01426 (19)	0.01029 (18)	0.01360 (18)
S1	0.0178 (2)	0.0297 (3)	0.0285 (2)	0.00845 (19)	0.00306 (18)	0.01438 (19)
O1	0.0270 (7)	0.0504 (9)	0.0255 (7)	0.0230 (7)	0.0082 (6)	0.0174 (6)
O2	0.0268 (8)	0.0346 (8)	0.0401 (8)	0.0044 (6)	0.0010 (6)	0.0087 (6)
O3	0.0324 (8)	0.0455 (9)	0.0432 (9)	0.0154 (7)	0.0091 (7)	0.0296 (7)
N1	0.0243 (8)	0.0332 (9)	0.0211 (7)	0.0132 (7)	0.0053 (6)	0.0109 (6)
N2	0.0229 (8)	0.0328 (9)	0.0281 (8)	0.0125 (7)	0.0071 (7)	0.0112 (7)
C1	0.0324 (11)	0.0617 (15)	0.0289 (10)	0.0259 (11)	0.0085 (9)	0.0196 (10)
C2	0.0384 (13)	0.0680 (17)	0.0339 (11)	0.0295 (12)	0.0035 (10)	0.0217 (11)
C3	0.0485 (14)	0.0455 (13)	0.0227 (10)	0.0210 (11)	0.0021 (9)	0.0139 (9)
C4	0.0422 (12)	0.0353 (11)	0.0224 (9)	0.0166 (10)	0.0103 (9)	0.0096 (8)
C5	0.0294 (10)	0.0245 (9)	0.0236 (9)	0.0101 (8)	0.0073 (8)	0.0080 (7)
C6	0.0297 (10)	0.0429 (12)	0.0262 (9)	0.0174 (9)	0.0123 (8)	0.0139 (8)
C7	0.0204 (9)	0.0343 (11)	0.0319 (10)	0.0118 (8)	0.0072 (8)	0.0115 (8)
C8	0.0246 (10)	0.0280 (10)	0.0388 (11)	0.0132 (8)	0.0078 (8)	0.0130 (8)

Cu1—O1	1.9775 (14)	C1—H1	0.9300
Cu1—N1	2.0051 (16)	C2—C3	1.371 (4)
Cu1—N2	2.0268 (17)	C2—H2	0.9300
Cu1—Cl1i	2.2901 (5)	C3—C4	1.390 (3)
Cu1—Cl1	2.6796 (7)	C3—H3	0.9300
Cl1—Cu1i	2.2901 (5)	C4—C5	1.386 (3)
S1—O2	1.4380 (16)	C4—H4	0.9300
S1—O3	1.4568 (15)	C5—C6	1.501 (3)
S1—O1	1.4916 (14)	C6—H6A	0.9700
S1—C8	1.774 (2)	C6—H6B	0.9700
N1—C5	1.345 (3)	C7—C8	1.519 (3)
N1—C1	1.346 (3)	C7—H7A	0.9700
N2—C6	1.475 (3)	C7—H7B	0.9700
N2—C7	1.492 (2)	C8—H8A	0.9700
N2—H1N	0.95 (3)	C8—H8B	0.9700
C1—C2	1.382 (3)
O1—Cu1—N1	169.95 (7)	C3—C2—C1	118.9 (2)
O1—Cu1—N2	92.73 (6)	C3—C2—H2	120.5
N1—Cu1—N2	81.18 (7)	C1—C2—H2	120.5
O1—Cu1—Cl1i	89.03 (4)	C2—C3—C4	119.45 (19)
N1—Cu1—Cl1i	95.57 (5)	C2—C3—H3	120.3
N2—Cu1—Cl1i	169.68 (5)	C4—C3—H3	120.3
O1—Cu1—Cl1	96.00 (5)	C5—C4—C3	118.9 (2)
N1—Cu1—Cl1	92.76 (5)	C5—C4—H4	120.5
N2—Cu1—Cl1	97.82 (5)	C3—C4—H4	120.5
Cl1i—Cu1—Cl1	92.091 (19)	N1—C5—C4	121.49 (19)
Cu1i—Cl1—Cu1	87.910 (19)	N1—C5—C6	115.27 (16)
O2—S1—O3	114.61 (10)	C4—C5—C6	123.21 (18)
O2—S1—O1	112.23 (10)	N2—C6—C5	108.83 (16)
O3—S1—O1	109.38 (9)	N2—C6—H6A	109.9
O2—S1—C8	107.16 (10)	C5—C6—H6A	109.9
O3—S1—C8	106.96 (10)	N2—C6—H6B	109.9
O1—S1—C8	105.98 (9)	C5—C6—H6B	109.9
S1—O1—Cu1	134.45 (9)	H6A—C6—H6B	108.3
C5—N1—C1	119.10 (17)	N2—C7—C8	110.64 (16)
C5—N1—Cu1	114.53 (13)	N2—C7—H7A	109.5
C1—N1—Cu1	126.36 (14)	C8—C7—H7A	109.5
C6—N2—C7	111.18 (16)	N2—C7—H7B	109.5
C6—N2—Cu1	108.32 (13)	C8—C7—H7B	109.5
C7—N2—Cu1	120.32 (13)	H7A—C7—H7B	108.1
C6—N2—H1N	104.2 (16)	C7—C8—S1	113.05 (14)
C7—N2—H1N	112.8 (16)	C7—C8—H8A	109.0
Cu1—N2—H1N	98.3 (16)	S1—C8—H8A	109.0
N1—C1—C2	122.1 (2)	C7—C8—H8B	109.0
N1—C1—H1	119.0	S1—C8—H8B	109.0
C2—C1—H1	119.0	H8A—C8—H8B	107.8
O1—Cu1—Cl1—Cu1i	−89.25 (4)	N1—Cu1—N2—C7	158.15 (16)
N1—Cu1—Cl1—Cu1i	95.68 (5)	Cl1i—Cu1—N2—C7	−129.6 (2)
N2—Cu1—Cl1—Cu1i	177.15 (5)	Cl1—Cu1—N2—C7	66.55 (14)
Cl1i—Cu1—Cl1—Cu1i	0.0	C5—N1—C1—C2	1.6 (4)
O2—S1—O1—Cu1	86.40 (15)	Cu1—N1—C1—C2	−179.12 (19)
O3—S1—O1—Cu1	−145.24 (13)	N1—C1—C2—C3	−1.4 (4)
C8—S1—O1—Cu1	−30.26 (16)	C1—C2—C3—C4	0.0 (4)
N1—Cu1—O1—S1	70.6 (4)	C2—C3—C4—C5	1.1 (4)
N2—Cu1—O1—S1	18.24 (15)	C1—N1—C5—C4	−0.5 (3)
Cl1i—Cu1—O1—S1	−171.93 (14)	Cu1—N1—C5—C4	−179.82 (16)
Cl1—Cu1—O1—S1	−79.93 (14)	C1—N1—C5—C6	177.54 (19)
O1—Cu1—N1—C5	−68.7 (4)	Cu1—N1—C5—C6	−1.8 (2)
N2—Cu1—N1—C5	−15.48 (14)	C3—C4—C5—N1	−0.9 (3)
Cl1i—Cu1—N1—C5	174.39 (13)	C3—C4—C5—C6	−178.7 (2)
Cl1—Cu1—N1—C5	82.02 (14)	C7—N2—C6—C5	−170.83 (17)
O1—Cu1—N1—C1	112.1 (4)	Cu1—N2—C6—C5	−36.51 (19)
N2—Cu1—N1—C1	165.2 (2)	N1—C5—C6—N2	25.8 (2)
Cl1i—Cu1—N1—C1	−4.89 (19)	C4—C5—C6—N2	−156.21 (19)
Cl1—Cu1—N1—C1	−97.27 (19)	C6—N2—C7—C8	−169.70 (17)
O1—Cu1—N2—C6	−159.28 (14)	Cu1—N2—C7—C8	62.2 (2)
N1—Cu1—N2—C6	28.76 (14)	N2—C7—C8—S1	−74.07 (19)
Cl1i—Cu1—N2—C6	101.0 (3)	O2—S1—C8—C7	−65.44 (17)
Cl1—Cu1—N2—C6	−62.84 (13)	O3—S1—C8—C7	171.21 (14)
O1—Cu1—N2—C7	−29.89 (15)	O1—S1—C8—C7	54.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O3ii	0.95 (3)	2.20 (3)	2.966 (2)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O3i	0.95 (3)	2.20 (3)	2.966 (2)	137 (2)

Symmetry code: (i) .