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

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ISSN: 2056-9890
Volume 68| Part 11| November 2012| Pages m1405-m1406

Hexa­kis­(μ3-1-methyl­thio­urea-κ3S:S:S)hexa­kis­[iodidocopper(I)]

aDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan, bDepartment of Chemistry, Government College of Science, Wahdat Road, Lahore, Pakistan, cDepartment of Chemistry, Government College University, Lahore, Pakistan, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: saeed_a786@hotmail.com

(Received 16 October 2012; accepted 18 October 2012; online 24 October 2012)

The title compound, [Cu6I6(C2H6N2S)6], was obtained from the reaction of copper(I) iodide with N-methyl­thio­urea (Metu) in equimolar amounts in acetonitile. The complex consists of two six-membered trinuclear Cu3S3I3 cores that combine through triply bridging Metu, forming a hexa­nuclear core which has -3 symmetry. The CuII atom is coordinated by three S atoms of Metu and one iodide ion in a distorted tetra­hedral geometry. The crystal structure is stabilized by N—H⋯I hydrogen bonds and cuprophilic inter­actions [Cu⋯Cu = 3.0264 (9) Å].

Related literature

For crystal structures of copper(I) complexes of thio­urea-type ligands, see: Ahmad et al. (2010[Ahmad, S., Altaf, M., Stoeckli-Evans, H., Ruffer, T., Lang, H., Mufakkar, M. & Abdul Waheed, A. (2010). J. Chem. Crystallogr. 40, 639-645.]); Bowmaker et al. (2009[Bowmaker, G. A., Hanna, J. V., Pakawatchai, C., Skelton, B. W., Thanyasirikul, Y. & White, A. H. (2009). Inorg. Chem. 48, 350-368.]); Li et al. (2005[Li, D., Shi, W. J. & Hou, L. (2005). Inorg. Chem. 44, 3907-3913.]); Lobana et al. (2003[Lobana, T. S., Sharma, R., Bermejo, E. & Castineiras, A. (2003). Inorg. Chem. 42, 7728-7730.], 2005[Lobana, T. S., Sharma, R., Sharma, R., Mehra, S., Castineiras, A. & Turner, R. (2005). Inorg. Chem. 44, 1914-1921.]); Khan et al. (2007[Khan, I. U., Mufakkar, M., Ahmad, S., Fun, H.-K. & Chantrapromma, S. (2007). Acta Cryst. E63, m2550-m2551.]); Mufakkar et al. (2007[Mufakkar, M., Ahmad, S., Khan, I. U., Fun, H.-K. & Chantrapromma, S. (2007). Acta Cryst. E63, m2384.], 2009[Mufakkar, M., Tahir, M. N., Ahmad, S., Shaheen, M. A. & Waheed, A. (2009). Acta Cryst. E65, m892-m893.], 2011[Mufakkar, M., Isab, A. A., Ruffer, T., Lang, H., Ahmad, S., Arshad, N. & Waheed, A. (2011). Transition Met. Chem. 36, 505-512.]); Stocker et al. (1997[Stocker, F. B., Troester, M. A. & Britton, D. (1997). Inorg. Chem. 35, 3145-3153.]); Zoufala et al. (2007[Zoufala, P., Rüffer, T., Lang, H., Ahmad, S. & Mufakkar, M. (2007). X-ray Struct. Anal. Online 23, x219-x220.]). For van der Waals radii and cuprophilic inter­actions, see: Siemeling et al. (1997[Siemeling, U., Vorfeld, U., Neumann, B. & Stammler, H.-G. (1997). Chem. Commun. pp. 1723-1724.]); Singh et al. (1997[Singh, K., Long, J. R. & Stavropoulos, P. (1997). J. Am. Chem. Soc. 119, 2942-2943.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu6I6(C2H6N2S)6]

  • Mr = 1683.65

  • Trigonal, [R \overline 3]

  • a = 21.7517 (1) Å

  • c = 7.6269 (1) Å

  • V = 3125.11 (5) Å3

  • Z = 3

  • Mo Kα radiation

  • μ = 7.79 mm−1

  • T = 296 K

  • 0.28 × 0.15 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]) Tmin = 0.179, Tmax = 0.338

  • 14898 measured reflections

  • 1995 independent reflections

  • 1649 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.061

  • S = 1.06

  • 1995 reflections

  • 65 parameters

  • H-atom parameters constrained

  • Δρmax = 1.32 e Å−3

  • Δρmin = −1.64 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯I1i 0.83 2.95 3.744 (3) 161
N1—H2N1⋯I1 0.80 2.90 3.698 (4) 173
N2—H1N2⋯I1ii 0.80 2.95 3.756 (3) 177
Symmetry codes: (i) [-y+{\script{2\over 3}}, x-y+{\script{4\over 3}}, z+{\script{1\over 3}}]; (ii) -x+y-1, -x+1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Copper(I) complexes with thiones possess a variety of structures ranging from mononuclear three- or four- coordinate species with trigonal planar and tetrahedral Cu(I) respectively to hexameric species with pseudo-four-coordinated geometry (Ahmad et al. 2010; Bowmaker et al., 2009; Li et al., 2005; Lobana et al., 2003, 2005; Khan et al. 2007; Mufakkar et al., 2007, 2009, 2011; Stocker et al., 1997; Zoufala et al., 2007). In some cases mononuclear units further aggregate to form polymeric structures, for example, [Cu6(PyT)6I6]n (where Pyt = pyridine-2-thione) (Li et al., 2005; Lobana et al., 2003, 2005). The present report describes the structure of a hexameric copper(I) complex, iodido(N-methylthiourea)copper(I), that is characterized by significant copper-copper interactions.

The structure of the title complex is shown in Figure 1. The complex is hexanuclear consisting of six [Metu-Cu—I] units, associated through sulfur atoms of N-methylthiourea. Three copper(I) iodides and three Metu ligands are combined through bridging sulfur atoms to form a six-membered trinuclear core, Cu3S3I3. Two six-membered trinuclear cores combine via µ3-sulfur atoms of Metu to form the centrosymmetric hexanuclear core, Cu6S6I6. Each copper within the complex is coordinated to three sulfur atoms of N-methylthiourea and with one iodide as a terminal ligand adopting a distorted tetrahedral geometry. The angles around Cu vary over the range 98.22 (5)–122.56 (3) °. The Cu—S bond distances are unequal; two are short (2.3164 (10) and 2.3210 (10) Å) and one is long (2.6057 (13) Å). However, they are within the range (2.30–2.60 Å) of the Cu—S bond distances found in other complexes. All of the Cu—I distances are equal (2.5379 (5) Å) and are in agreement with the values reported in the literature. The hexanuclear structure is supported by significant intermolecular N—H···I hydrogen bonding (Table 1) and Cu···Cu interactions. The Cu···Cu distance of 3.0264 (9) Å is close to similar distances observed in other complexes. However, this value is slightly larger than the sum of the van der Waals radii of two copper atoms (2.80 Å) (Siemeling et al. 1997; Singh et al., 1997). Similar hexanuclear core structures have been reported for [Cu6(Imt)6I6]n and [Cu6(Pyt)6I6]n (Imt = imidazolidine-2-thione and Pyt = pyridine-2-thione; Lobana et al., 2003, 2005).

Related literature top

For crystal structures of copper(I) complexes of thiourea-type ligands, see: Ahmad et al. (2010); Bowmaker et al. (2009); Li et al. (2005); Lobana et al. (2003, 2005); Khan et al. (2007); Mufakkar et al. (2007, 2009, 2011); Stocker et al. (1997); Zoufala et al. (2007). For van der Waals radii and cuprophilic interactions, see: Siemeling et al. (1997); Singh et al. (1997).

Experimental top

The title compund was prepared by mixing solutions of copper(I) iodide (1.0 mmol) in 10 ml acetonitrile and N-methylthiourea (1.0 mmol) in acetonitrile (15 ml). The mixture was stirred for half an hour and then filtered. The resulting colourless solution when allowed to stand for 24 h yielded white crystals suitable for X-ray structure analysis.

Refinement top

All H atoms were placed in calculated positions with C—H = 0.96 Å, N—H = 0.80-0.83 Å, and with Uiso(H) = 1.2 Ueq(N) or 1.5 Ueq(C)

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. Symmetry codes: (a) 1-y, 2+x-y, z; (b) -1-x+y, 1-x, z; (c) -x, 2-y, -z; (d) -1+y, -x+y, -z; (e) 1+x-y, 1+x, -z.
Hexakis(µ3-1-methylthiourea- κ3S:S:S)hexakis[iodidocopper(I)] top
Crystal data top
[Cu6I6(C2H6N2S)6]Dx = 2.684 Mg m3
Mr = 1683.65Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 4617 reflections
Hall symbol: -R 3θ = 2.2–26.6°
a = 21.7517 (1) ŵ = 7.79 mm1
c = 7.6269 (1) ÅT = 296 K
V = 3125.11 (5) Å3Block, colourless
Z = 30.28 × 0.15 × 0.14 mm
F(000) = 2340
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
1995 independent reflections
Radiation source: fine-focus sealed tube1649 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 29.8°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 3030
Tmin = 0.179, Tmax = 0.338k = 3030
14898 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0202P)2 + 17.0381P]
where P = (Fo2 + 2Fc2)/3
1995 reflections(Δ/σ)max < 0.001
65 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = 1.64 e Å3
Crystal data top
[Cu6I6(C2H6N2S)6]Z = 3
Mr = 1683.65Mo Kα radiation
Trigonal, R3µ = 7.79 mm1
a = 21.7517 (1) ÅT = 296 K
c = 7.6269 (1) Å0.28 × 0.15 × 0.14 mm
V = 3125.11 (5) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
1995 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
1649 reflections with I > 2σ(I)
Tmin = 0.179, Tmax = 0.338Rint = 0.035
14898 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.061H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0202P)2 + 17.0381P]
where P = (Fo2 + 2Fc2)/3
1995 reflectionsΔρmax = 1.32 e Å3
65 parametersΔρmin = 1.64 e Å3
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
xyzUiso*/Ueq
I10.082885 (13)0.829523 (13)0.17796 (4)0.04164 (9)
Cu10.04125 (3)0.91805 (3)0.12398 (9)0.05416 (16)
N10.10312 (17)0.76485 (17)0.3103 (5)0.0478 (8)
H1N10.12640.72320.34550.057*
H2N10.06160.78050.29090.057*
N20.19615 (15)0.78569 (16)0.2972 (4)0.0394 (7)
H1N20.20670.81510.27210.047*
C10.12810 (18)0.80754 (17)0.2777 (5)0.0330 (7)
C20.2500 (2)0.7132 (2)0.3356 (6)0.0489 (10)
H2A0.29450.71110.35730.073*
H2B0.23630.69700.43750.073*
H2C0.25490.68340.23750.073*
S10.07031 (4)0.89448 (4)0.21477 (14)0.0388 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04018 (14)0.03935 (13)0.05508 (16)0.02713 (11)0.00274 (11)0.00505 (11)
Cu10.0380 (3)0.0348 (2)0.0945 (4)0.0218 (2)0.0005 (3)0.0007 (3)
N10.0340 (16)0.0398 (17)0.071 (2)0.0197 (14)0.0127 (16)0.0209 (17)
N20.0316 (14)0.0353 (15)0.0534 (19)0.0182 (13)0.0053 (13)0.0115 (14)
C10.0318 (16)0.0306 (16)0.0369 (17)0.0157 (13)0.0033 (14)0.0031 (13)
C20.0305 (17)0.042 (2)0.063 (3)0.0101 (16)0.0039 (18)0.0181 (19)
S10.0266 (4)0.0264 (4)0.0635 (6)0.0133 (3)0.0024 (4)0.0039 (4)
Geometric parameters (Å, º) top
I1—Cu12.5379 (5)N2—C11.317 (4)
Cu1—S1i2.3164 (10)N2—C21.449 (5)
Cu1—S12.3210 (10)N2—H1N20.8028
Cu1—S1ii2.6057 (13)C1—S11.735 (3)
Cu1—Cu1iii3.0264 (9)C2—H2A0.9600
Cu1—Cu1ii3.0264 (9)C2—H2B0.9600
N1—C11.313 (4)C2—H2C0.9600
N1—H1N10.8316S1—Cu1iv2.3164 (10)
N1—H2N10.8039S1—Cu1iii2.6057 (13)
S1i—Cu1—S198.22 (5)C1—N2—C2124.5 (3)
S1i—Cu1—I1122.56 (3)C1—N2—H1N2113.8
S1—Cu1—I1120.95 (3)C2—N2—H1N2121.2
S1i—Cu1—S1ii102.80 (4)N1—C1—N2120.7 (3)
S1—Cu1—S1ii102.67 (4)N1—C1—S1119.5 (3)
I1—Cu1—S1ii106.80 (3)N2—C1—S1119.7 (3)
S1i—Cu1—Cu1iii118.09 (3)N2—C2—H2A109.5
S1—Cu1—Cu1iii56.49 (3)N2—C2—H2B109.5
I1—Cu1—Cu1iii118.39 (2)H2A—C2—H2B109.5
S1ii—Cu1—Cu1iii47.86 (3)N2—C2—H2C109.5
S1i—Cu1—Cu1ii56.52 (3)H2A—C2—H2C109.5
S1—Cu1—Cu1ii118.03 (3)H2B—C2—H2C109.5
I1—Cu1—Cu1ii119.84 (2)C1—S1—Cu1iv115.65 (12)
S1ii—Cu1—Cu1ii47.96 (3)C1—S1—Cu1115.53 (12)
Cu1iii—Cu1—Cu1ii85.08 (3)Cu1iv—S1—Cu1123.88 (5)
C1—N1—H1N1126.2C1—S1—Cu1iii98.60 (12)
C1—N1—H2N1116.1Cu1iv—S1—Cu1iii75.63 (3)
H1N1—N1—H2N1117.6Cu1—S1—Cu1iii75.55 (3)
C2—N2—C1—N17.1 (6)Cu1iii—Cu1—S1—C192.76 (14)
C2—N2—C1—S1174.9 (3)Cu1ii—Cu1—S1—C1154.78 (14)
N1—C1—S1—Cu1iv171.7 (3)S1i—Cu1—S1—Cu1iv57.15 (8)
N2—C1—S1—Cu1iv10.3 (4)I1—Cu1—S1—Cu1iv166.73 (4)
N1—C1—S1—Cu115.6 (4)S1ii—Cu1—S1—Cu1iv48.03 (7)
N2—C1—S1—Cu1166.4 (3)Cu1iii—Cu1—S1—Cu1iv61.20 (5)
N1—C1—S1—Cu1iii93.6 (3)Cu1ii—Cu1—S1—Cu1iv0.83 (8)
N2—C1—S1—Cu1iii88.4 (3)S1i—Cu1—S1—Cu1iii118.35 (4)
S1i—Cu1—S1—C1148.90 (13)I1—Cu1—S1—Cu1iii105.53 (3)
I1—Cu1—S1—C112.78 (15)S1ii—Cu1—S1—Cu1iii13.17 (4)
S1ii—Cu1—S1—C1105.92 (14)Cu1ii—Cu1—S1—Cu1iii62.03 (4)
Symmetry codes: (i) y+1, xy+2, z; (ii) xy+1, x+1, z; (iii) y1, x+y, z; (iv) x+y1, x+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···I1v0.832.953.744 (3)161
N1—H2N1···I10.802.903.698 (4)173
N2—H1N2···I1iv0.802.953.756 (3)177
Symmetry codes: (iv) x+y1, x+1, z; (v) y+2/3, xy+4/3, z+1/3.

Experimental details

Crystal data
Chemical formula[Cu6I6(C2H6N2S)6]
Mr1683.65
Crystal system, space groupTrigonal, R3
Temperature (K)296
a, c (Å)21.7517 (1), 7.6269 (1)
V3)3125.11 (5)
Z3
Radiation typeMo Kα
µ (mm1)7.79
Crystal size (mm)0.28 × 0.15 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.179, 0.338
No. of measured, independent and
observed [I > 2σ(I)] reflections
14898, 1995, 1649
Rint0.035
(sin θ/λ)max1)0.700
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.061, 1.06
No. of reflections1995
No. of parameters65
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0202P)2 + 17.0381P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.32, 1.64

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···I1i0.83002.95003.744 (3)161.00
N1—H2N1···I10.80002.90003.698 (4)173.00
N2—H1N2···I1ii0.80002.95003.756 (3)177.00
Symmetry codes: (i) y+2/3, xy+4/3, z+1/3; (ii) x+y1, x+1, z.
 

Acknowledgements

The authors gratefully acknowledge Universiti Sains Malaysia and Government College University, Lahore, for providing X-ray facilities.

References

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Volume 68| Part 11| November 2012| Pages m1405-m1406
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