Di-μ-chlorido-bis­{aqua­chlorido[2,2′-thio­bis(pyridine N-oxide)-κO]copper(II)}

Seidel, R.W.; Oppel, I.M.

doi:10.1107/S1600536809011076

metal-organic compounds

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doi:10.1107/S1600536809011076

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Di-μ-chlorido-bis{aquachlorido[2,2′-thiobis(pyridine N-oxide)-κO]copper(II)}

Rüdiger W. Seidel ^a ^* and Iris M. Oppel ^a

^aAnalytische Chemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44780 Bochum, Germany
^*Correspondence e-mail: ruediger.seidel@rub.de

(Received 24 March 2009; accepted 25 March 2009; online 28 March 2009)

The crystal structure of the title compound, [Cu₂Cl₄(C₁₀H₈N₂O₂S)₂(H₂O)₂], comprises neutral centrosymmetric μ-chloride-bridged dinuclear units. Each Cu^II ion is pentacoordinated by three chloride ligands, a pyridine N-oxide O atom and a water molecule. Intra- and intermolecular O—H⋯O hydrogen bonds occur between the coordinated water molecules and the uncoordinated and coordinated pyridine N-oxide groups of the 2,2′-thiobis(pyridine N-oxide) ligands, respectively.

Related literature

For the potential of pyridine N-oxide-based building blocks in the construction of coordination polymers and crystal engineering, see: Sun et al. (2008 ) and references cited therein. For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For a copper-catalysed example of in situ S—S and S—Csp² bond cleavage and rearrangement of an related disulfide, see: Wang et al. (2007 ).

Experimental

Crystal data

[Cu₂Cl₄(C₁₀H₈N₂O₂S)₂(H₂O)₂]
M_r = 745.40
Monoclinic, P 2₁ /c
a = 6.7552 (18) Å
b = 11.430 (3) Å
c = 17.375 (3) Å
β = 95.516 (17)°
V = 1335.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.19 mm⁻¹
T = 294 K
0.27 × 0.21 × 0.19 mm

Data collection

Siemens P4 four-circle diffractometer
Absorption correction: ψ scan (ABSPsiScan in PLATON; Spek, 2009 ) T_min = 0.529, T_max = 0.663
3316 measured reflections
2349 independent reflections
1736 reflections with I > 2(I)
R_int = 0.058
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.088
S = 1.02
2349 reflections
178 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.81 (2)	2.13 (2)	2.919 (4)	167 (5)
O2—H2B⋯O11ⁱⁱ	0.82 (2)	1.97 (2)	2.789 (5)	177 (5)
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

Data collection: XSCANS (Bruker, 1999 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011076/dn2439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011076/dn2439Isup2.hkl

checkCIF report

Comment top

Pyridine-N-oxide based ligands have attracted a considerable interest in crystal engineering and the synthesis of coordination polymers (Sun et al., 2008).

The title compound, namely bis(µ-chlorido)-diaqua-dichlorido- bis(2,2'-thiobis(pyridine-N-oxide-κO)-dicopper(II), is a neutral dinuclear complex with a central Cu₂Cl₂-ring exhibiting C_i point symmetry (Fig. 1). The unit cell contains two molecules which reside on a crystallographic centre of inversion. Each Cu²⁺ ion adopts a distorted square-pyramidal coordination sphere. Two equatorial cis-coordination sites are occupied by the two bridging chlorido ligands. Another chlorido ligand in monodentate coordination mode and an oxygen atom of the pyridine-N-oxide group of the 2,2'-thiobis(pyridine-N-oxide) are located at the remaining two cis-sites. A water molecule binds to the axial position. The molecular geometry parameters are within normal ranges. The dihedral angle Cu(µ-Cl)₂/CuClO(N-oxide) is 17.0 (1)°. The angle between the mean planes of the rings N1—C6 and N11—C16 is 66.4 (1)°.

The coordinated water molecule forms an intramolecular hydrogen bond to O11 of the non-coordinating pyridine-N-oxide group of the 2,2'-thiobis(pyridine-N-oxide) ligand. The graph set here is S(12) (Bernstein et al., 1995). The second water hydrogen atom is involved in an intermolecular hydrogen bond to O1 of the coordinating pyridine-N-oxide group with a centrosymmetric R²₂(8) motif. This leads to the formation of infitine chains via hydrogen bonding extending in the [100] direction with a period corresponding to the crystallographic a axis. Hydrogen bonding details are listed in Table 2.

To the best of our knowledge the title compound is the first coordination compound and the first crystal structure comprising 2,2-thiobis(pyridine-N-oxide).

Related literature top

For the potential of pyridine N-oxide-based building blocks in the construction of coordination polymers and crystal engineering, see: Sun et al. (2008) and references cited therein. For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For a copper-catalysed example of in situ S—S and S—Csp² bond cleavage and rearrangement of an related disulfide, see: Wang et al. (2007).

Experimental top

A dark-yellow crystal of the title compound suitable for X-ray diffraction was obtained when equimolar amounts of CuCl₂ and 2,2'-dithiobis(pyridine-N-oxide) (Aldrich) were dissolved in methanol and the solution was left at ambient temperature. The crystal was found whithin dark-green unidentified material. The origin of the new 2,2'-thiobis(pyridine-N-oxide) ligand is not clear. Either a trace impurity in the starting material or an in situ cleavage and rearrangement of S—S and S—C(sp²) bonds can be considered. A copper catalysed example of the latter with an related disulfide was reported by Wang et al. (2007). As far we can ascertain no synthetic route to 2,2'-thiobis(pyridine-N-oxide) has been reported in the literature.

Computing details top

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS (Bruker, 1999); data reduction: XSCANS (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the title compound with 50% probability of the displacement ellipsoids. Hydrogen atoms are drawn at arbitrary size. Hydrogen bonds are represented by dashed lines. For the symmetry codes see Table 1.
	Fig. 2. Hydrogen bonding interactions between to adjacent molecules in the crystal structure of the title compound. Hydrogen bonds are represented by dashed lines. For the symmetry codes see Table 2.

Di-µ-chlorido-bis{aquachlorido[2,2'-thiobis(pyridine N-oxide)-κO]copper(II)} top

Crystal data top

[Cu₂Cl₄(C₁₀H₈N₂O₂S)₂(H₂O)₂]	F(000) = 748
M_r = 745.40	D_x = 1.854 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.7552 (18) Å	θ = 5.1–18.0°
b = 11.430 (3) Å	µ = 2.19 mm⁻¹
c = 17.375 (3) Å	T = 294 K
β = 95.516 (17)°	Prism, dark-yellow
V = 1335.4 (6) Å³	0.27 × 0.21 × 0.19 mm
Z = 2

Data collection top

Siemens P4 four-circle diffractometer	1736 reflections with I > 2(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω scans	h = −8→1
Absorption correction: ψ scan (ABSPsiScan in PLATON; Spek, 2009)	k = −1→13
T_min = 0.529, T_max = 0.663	l = −20→20
3316 measured reflections	3 standard reflections every 97 reflections
2349 independent reflections	intensity decay: none

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0347P)²] where P = (F_o² + 2F_c²)/3
2349 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Cu₂Cl₄(C₁₀H₈N₂O₂S)₂(H₂O)₂]	V = 1335.4 (6) Å³
M_r = 745.40	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7552 (18) Å	µ = 2.19 mm⁻¹
b = 11.430 (3) Å	T = 294 K
c = 17.375 (3) Å	0.27 × 0.21 × 0.19 mm
β = 95.516 (17)°

Data collection top

Siemens P4 four-circle diffractometer	1736 reflections with I > 2(I)
Absorption correction: ψ scan (ABSPsiScan in PLATON; Spek, 2009)	R_int = 0.058
T_min = 0.529, T_max = 0.663	3 standard reflections every 97 reflections
3316 measured reflections	intensity decay: none
2349 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.40 e Å⁻³
2349 reflections	Δρ_min = −0.53 e Å⁻³
178 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

	x	y	z	U_iso*/U_eq
Cu1	0.36057 (7)	0.52270 (5)	0.07537 (3)	0.02340 (16)
Cl1	0.42569 (17)	0.52142 (11)	0.20449 (6)	0.0365 (3)
Cl2	0.34708 (15)	0.57187 (10)	−0.05629 (6)	0.0273 (3)
S1	0.42443 (17)	0.79699 (11)	0.11518 (7)	0.0343 (3)
O1	0.1176 (4)	0.6210 (3)	0.07498 (15)	0.0272 (7)
O2	0.1784 (5)	0.3623 (3)	0.05848 (18)	0.0325 (8)
H2A	0.086 (5)	0.372 (4)	0.026 (2)	0.039*
H2B	0.231 (7)	0.305 (3)	0.040 (2)	0.039*
N1	0.0804 (5)	0.6857 (3)	0.13620 (19)	0.0250 (8)
C2	−0.0843 (6)	0.6616 (4)	0.1706 (2)	0.0290 (11)
H2	−0.1683	0.6013	0.1521	0.035*
C3	−0.1287 (7)	0.7269 (4)	0.2335 (3)	0.0378 (12)
H3	−0.2435	0.7108	0.2572	0.045*
C4	−0.0060 (7)	0.8142 (4)	0.2611 (3)	0.0386 (12)
H4	−0.0342	0.8569	0.3043	0.046*
C5	0.1619 (7)	0.8391 (4)	0.2242 (3)	0.0352 (11)
H5	0.2461	0.8996	0.2423	0.042*
C6	0.2049 (6)	0.7744 (4)	0.1606 (2)	0.0250 (10)
O11	0.6518 (4)	0.8360 (3)	0.00176 (19)	0.0412 (9)
N11	0.4647 (5)	0.8581 (3)	−0.0254 (2)	0.0315 (9)
C12	0.3202 (7)	0.8442 (4)	0.0239 (2)	0.0276 (11)
C13	0.1254 (6)	0.8656 (4)	−0.0018 (2)	0.0292 (11)
H13	0.0267	0.8566	0.0315	0.035*
C14	0.0761 (7)	0.9005 (4)	−0.0771 (3)	0.0378 (12)
H14	−0.0560	0.9141	−0.0951	0.045*
C15	0.2246 (8)	0.9151 (4)	−0.1254 (3)	0.0425 (13)
H15	0.1930	0.9400	−0.1761	0.051*
C16	0.4167 (8)	0.8932 (4)	−0.0992 (3)	0.0395 (13)
H16	0.5161	0.9024	−0.1322	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0210 (3)	0.0273 (3)	0.0224 (3)	0.0022 (3)	0.0041 (2)	−0.0021 (2)
Cl1	0.0376 (7)	0.0499 (7)	0.0224 (6)	0.0122 (6)	0.0045 (5)	0.0007 (5)
Cl2	0.0246 (6)	0.0331 (6)	0.0249 (6)	0.0063 (5)	0.0050 (4)	−0.0017 (5)
S1	0.0216 (6)	0.0443 (7)	0.0370 (7)	−0.0053 (6)	0.0028 (5)	0.0023 (6)
O1	0.0223 (16)	0.0342 (17)	0.0250 (16)	0.0056 (14)	0.0018 (13)	−0.0109 (14)
O2	0.0259 (19)	0.0323 (19)	0.038 (2)	−0.0022 (16)	−0.0030 (15)	−0.0023 (16)
N1	0.0210 (19)	0.029 (2)	0.0253 (19)	0.0026 (17)	0.0042 (16)	−0.0004 (17)
C2	0.021 (2)	0.031 (3)	0.036 (3)	−0.001 (2)	0.006 (2)	0.000 (2)
C3	0.029 (3)	0.053 (3)	0.033 (3)	0.006 (3)	0.008 (2)	−0.001 (2)
C4	0.046 (3)	0.042 (3)	0.030 (3)	0.008 (3)	0.011 (2)	−0.006 (2)
C5	0.041 (3)	0.028 (3)	0.037 (3)	−0.005 (2)	−0.001 (2)	−0.005 (2)
C6	0.019 (2)	0.030 (2)	0.027 (2)	0.001 (2)	0.0029 (19)	0.0001 (19)
O11	0.0196 (17)	0.047 (2)	0.059 (2)	−0.0015 (16)	0.0111 (16)	−0.0083 (17)
N11	0.023 (2)	0.026 (2)	0.047 (2)	−0.0057 (17)	0.0112 (18)	−0.0080 (19)
C12	0.028 (3)	0.022 (2)	0.035 (3)	−0.008 (2)	0.011 (2)	−0.007 (2)
C13	0.020 (2)	0.032 (3)	0.037 (3)	−0.002 (2)	0.012 (2)	−0.002 (2)
C14	0.037 (3)	0.037 (3)	0.040 (3)	−0.002 (2)	0.002 (2)	0.007 (2)
C15	0.048 (3)	0.049 (3)	0.030 (3)	−0.006 (3)	0.007 (2)	0.002 (2)
C16	0.049 (3)	0.045 (3)	0.028 (3)	−0.010 (3)	0.020 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.988 (3)	C3—H3	0.9300
Cu1—O2	2.212 (3)	C4—C5	1.386 (6)
Cu1—Cl1	2.2443 (12)	C4—H4	0.9300
Cu1—Cl2ⁱ	2.3031 (12)	C5—C6	1.384 (6)
Cu1—Cl2	2.3489 (12)	C5—H5	0.9300
Cl2—Cu1ⁱ	2.3031 (12)	O11—N11	1.331 (5)
S1—C12	1.758 (5)	N11—C16	1.353 (6)
S1—C6	1.764 (4)	N11—C12	1.369 (5)
O1—N1	1.339 (4)	C12—C13	1.370 (6)
O2—H2A	0.81 (2)	C13—C14	1.378 (6)
O2—H2B	0.82 (2)	C13—H13	0.9300
N1—C2	1.341 (5)	C14—C15	1.379 (6)
N1—C6	1.359 (5)	C14—H14	0.9300
C2—C3	1.381 (6)	C15—C16	1.357 (7)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.355 (7)	C16—H16	0.9300

O1—Cu1—O2	91.10 (12)	C3—C4—H4	120.4
O1—Cu1—Cl1	95.13 (8)	C5—C4—H4	120.4
O2—Cu1—Cl1	100.39 (9)	C6—C5—C4	120.3 (4)
O1—Cu1—Cl2ⁱ	169.61 (9)	C6—C5—H5	119.9
O2—Cu1—Cl2ⁱ	93.77 (9)	C4—C5—H5	119.9
Cl1—Cu1—Cl2ⁱ	93.00 (4)	N1—C6—C5	118.5 (4)
O1—Cu1—Cl2	84.65 (8)	N1—C6—S1	119.4 (3)
O2—Cu1—Cl2	95.75 (9)	C5—C6—S1	121.9 (3)
Cl1—Cu1—Cl2	163.86 (5)	O11—N11—C16	121.7 (4)
Cl2ⁱ—Cu1—Cl2	85.74 (4)	O11—N11—C12	117.8 (4)
Cu1ⁱ—Cl2—Cu1	94.26 (4)	C16—N11—C12	120.5 (4)
C12—S1—C6	99.6 (2)	N11—C12—C13	119.7 (4)
N1—O1—Cu1	121.8 (2)	N11—C12—S1	110.7 (3)
Cu1—O2—H2A	111 (4)	C13—C12—S1	129.6 (3)
Cu1—O2—H2B	117 (3)	C12—C13—C14	119.9 (4)
H2A—O2—H2B	100 (5)	C12—C13—H13	120.1
O1—N1—C2	117.9 (4)	C14—C13—H13	120.1
O1—N1—C6	120.1 (3)	C13—C14—C15	119.3 (5)
C2—N1—C6	122.0 (4)	C13—C14—H14	120.3
N1—C2—C3	119.6 (4)	C15—C14—H14	120.3
N1—C2—H2	120.2	C16—C15—C14	120.1 (5)
C3—C2—H2	120.2	C16—C15—H15	120.0
C4—C3—C2	120.4 (4)	C14—C15—H15	120.0
C4—C3—H3	119.8	N11—C16—C15	120.5 (4)
C2—C3—H3	119.8	N11—C16—H16	119.7
C3—C4—C5	119.2 (4)	C15—C16—H16	119.7

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱⁱ	0.81 (2)	2.13 (2)	2.919 (4)	167 (5)
O2—H2B···O11ⁱ	0.82 (2)	1.97 (2)	2.789 (5)	177 (5)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₄(C₁₀H₈N₂O₂S)₂(H₂O)₂]
M_r	745.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	6.7552 (18), 11.430 (3), 17.375 (3)
β (°)	95.516 (17)
V (Å³)	1335.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.19
Crystal size (mm)	0.27 × 0.21 × 0.19

Data collection
Diffractometer	Siemens P4 four-circle diffractometer
Absorption correction	ψ scan (ABSPsiScan in PLATON; Spek, 2009)
T_min, T_max	0.529, 0.663
No. of measured, independent and observed [I > 2(I)] reflections	3316, 2349, 1736
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.088, 1.02
No. of reflections	2349
No. of parameters	178
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.53

Computer programs: XSCANS (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.81 (2)	2.13 (2)	2.919 (4)	167 (5)
O2—H2B···O11ⁱⁱ	0.82 (2)	1.97 (2)	2.789 (5)	177 (5)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z.

Acknowledgements

Professor William S. Sheldrick is gratefully acknowledged for generous support. RWS thanks Dr Tobias van Almsick for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1999). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, H.-L., Wang, Z.-M., Gao, S. & Batten, S. R. (2008). CrystEngComm, 10, 1796–1802. Web of Science CSD CrossRef CAS Google Scholar
Wang, J., Zheng, S.-L., Hu, S., Zhang, Y.-H. & Tong, M.-L. (2007). Inorg. Chem. 46, 795–800. Web of Science CSD CrossRef PubMed CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di-μ-chlorido-bis­­{aqua­chlorido[2,2′-thio­bis­(pyridine N-oxide)-κO]copper(II)}

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Di-μ-chlorido-bis{aquachlorido[2,2′-thiobis(pyridine N-oxide)-κO]copper(II)}