PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m1023.
Published online 2010 July 31. doi:  10.1107/S1600536810029302
PMCID: PMC3007489

(2,2′-Dimethyl-4,4′-bi-1,3-thia­zole-κ2 N,N′)diiodidomercury(II)

Abstract

In the title compound, [HgI2(C8H8N2S2)], the HgII atom is four-coordinated in a distorted tetra­hedral geometry by two N atoms from a 2,2′-dimethyl-4,4′-bithia­zole ligand and two I atoms. In the crystal structure, adjacent mol­ecules are connected by π–π contacts between the thia­zole rings [centroid–centroid distance = 3.591 (3) Å].

Related literature

For metal complexes with the 2,2′-dimethyl-4,4′-bithia­zole ligand, see: Al-Hashemi et al. (2009 [triangle]); Khavasi et al. (2008 [triangle]); Notash et al. (2008 [triangle]). For related structures, see: Safari et al. (2009 [triangle]); Tadayon Pour et al. (2008 [triangle]); Yousefi et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1023-scheme1.jpg

Experimental

Crystal data

  • [HgI2(C8H8N2S2)]
  • M r = 650.67
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1023-efi1.jpg
  • a = 12.9059 (10) Å
  • b = 14.8605 (11) Å
  • c = 14.9432 (11) Å
  • V = 2865.9 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 15.31 mm−1
  • T = 100 K
  • 0.18 × 0.16 × 0.11 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.085, T max = 0.191
  • 27850 measured reflections
  • 3135 independent reflections
  • 2746 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.058
  • S = 1.00
  • 3135 reflections
  • 138 parameters
  • H-atom parameters constrained
  • Δρmax = 0.74 e Å−3
  • Δρmin = −1.36 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810029302/hy2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029302/hy2334Isup2.hkl

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

Acknowledgments

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

supplementary crystallographic information

Comment

Khavasi et al. (2008) reported the synthesis and structure of 2,2'-dimethyl-4,4'-bithiazole (dm4bt) by single crystal X-ray diffraction methods. Dm4bt is a good bidentate ligand, and numerous complexes with dm4bt have been prepared, such as those of zinc (Khavasi et al., 2008), thallium (Notash et al., 2008), cadmium (Notash et al., 2008) and copper (Al-Hashemi et al., 2009). For further investigation of dm4bt, we synthezised the title complex, and report herein its crystal structure.

In the title compound (Fig. 1), the HgII atom is four-coordinated in a distorted tetrahedral geometry by two N atoms from a 2,2'-dimethyl-4,4'-bithiazole ligand and two I atoms. The Hg—N and Hg—I bond lengths and angles (Table 1) are within normal range of [Hg(SCN)2(dm4bt)] (Safari et al., 2009), [HgI2(4,4'-dmbpy)] (Yousefi et al., 2008) and [HgI2(5,5'-dmbpy)] (Tadayon Pour et al., 2008) (4,4'-dmbpy = 4,4'-dimethyl-2,2'-bipyridine; 5,5'-dmbpy = 5,5'-dimethyl-2, 2'-bipyridine). In the crystal structure, π–π contacts (Fig. 2) between the thiazole rings, Cg2···Cg3i [symmetry code: (i) 1-x, 1-y, -z. Cg2 and Cg3 are centroids of the S1, C1, N1, C3, C2 ring and the S2, C5, C4, N2, C6 ring], stabilize the structure, with a centroid–centroid distance of 3.591 (3) Å.

Experimental

A solution of 2,2'-dimethyl-4,4'-bithiazole (0.20 g, 1.00 mmol) in methanol (15 ml) was added to a solution of HgI2 (0.46 g, 1.00 mmol) in methanol (15 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained after one week by methanol diffusion to a colorless solution of the title compound in DMSO (yield: 0.48 g, 73.8%).

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 (CH) and 0.98 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing diagram of the title compound.

Crystal data

[HgI2(C8H8N2S2)]Dx = 3.016 Mg m3
Mr = 650.67Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 4823 reflections
a = 12.9059 (10) Åθ = 4–27°
b = 14.8605 (11) ŵ = 15.31 mm1
c = 14.9432 (11) ÅT = 100 K
V = 2865.9 (4) Å3Prism, colorless
Z = 80.18 × 0.16 × 0.11 mm
F(000) = 2304

Data collection

Bruker APEXII CCD diffractometer3135 independent reflections
Radiation source: fine-focus sealed tube2746 reflections with I > 2σ(I)
graphiteRint = 0.060
[var phi] and ω scansθmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −16→16
Tmin = 0.085, Tmax = 0.191k = −18→18
27850 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.030P)2 + 3.P] where P = (Fo2 + 2Fc2)/3
3135 reflections(Δ/σ)max = 0.002
138 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = −1.36 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Hg10.510845 (16)0.378820 (14)0.225249 (14)0.01739 (7)
I10.59477 (3)0.23923 (3)0.14062 (3)0.02478 (10)
I20.46410 (3)0.41700 (2)0.39435 (2)0.02213 (9)
S10.61688 (11)0.68779 (9)0.15627 (10)0.0197 (3)
S20.24214 (11)0.45250 (10)0.00224 (9)0.0209 (3)
N10.5553 (3)0.5267 (3)0.1740 (3)0.0169 (9)
N20.3846 (3)0.4293 (3)0.1177 (3)0.0158 (9)
C10.6287 (4)0.5813 (4)0.2004 (4)0.0177 (11)
C20.5076 (4)0.6562 (4)0.1008 (4)0.0203 (12)
H2A0.46780.69480.06370.024*
C30.4849 (4)0.5682 (4)0.1169 (4)0.0181 (11)
C40.3987 (4)0.5150 (4)0.0821 (3)0.0166 (11)
C50.3287 (4)0.5378 (4)0.0189 (4)0.0186 (11)
H5A0.32780.5936−0.01210.022*
C60.3056 (4)0.3887 (4)0.0811 (4)0.0177 (11)
C70.7144 (5)0.5550 (4)0.2603 (4)0.0271 (13)
H7A0.68600.53500.31780.041*
H7B0.76020.60660.27000.041*
H7C0.75370.50570.23300.041*
C80.2714 (5)0.2959 (4)0.1047 (4)0.0260 (13)
H8A0.25840.29230.16920.039*
H8B0.32570.25280.08820.039*
H8C0.20760.28150.07210.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.01885 (11)0.01823 (11)0.01509 (11)0.00215 (8)−0.00002 (8)0.00063 (8)
I10.0298 (2)0.0248 (2)0.01979 (19)0.01150 (16)0.00339 (16)0.00036 (15)
I20.0271 (2)0.0226 (2)0.01672 (18)0.00144 (15)0.00188 (14)−0.00428 (14)
S10.0204 (7)0.0173 (7)0.0214 (7)0.0005 (5)−0.0012 (5)0.0021 (5)
S20.0201 (7)0.0259 (8)0.0166 (7)0.0026 (5)−0.0042 (5)0.0006 (6)
N10.018 (2)0.019 (2)0.013 (2)0.0015 (18)0.0012 (18)0.0033 (18)
N20.016 (2)0.018 (2)0.013 (2)0.0047 (17)0.0009 (17)−0.0022 (18)
C10.018 (3)0.021 (3)0.014 (3)0.002 (2)0.000 (2)0.000 (2)
C20.015 (3)0.025 (3)0.021 (3)0.005 (2)0.000 (2)−0.001 (2)
C30.017 (3)0.026 (3)0.011 (3)0.005 (2)0.004 (2)0.001 (2)
C40.015 (3)0.022 (3)0.013 (3)0.002 (2)0.001 (2)−0.003 (2)
C50.020 (3)0.018 (3)0.018 (3)0.002 (2)0.007 (2)−0.003 (2)
C60.018 (3)0.019 (3)0.016 (3)0.004 (2)0.001 (2)−0.005 (2)
C70.027 (3)0.027 (3)0.028 (3)−0.004 (2)−0.010 (3)0.006 (3)
C80.028 (3)0.023 (3)0.027 (3)−0.001 (2)−0.007 (3)0.000 (3)

Geometric parameters (Å, °)

Hg1—N12.397 (4)C2—C31.361 (8)
Hg1—N22.408 (4)C2—H2A0.9500
Hg1—I12.6600 (4)C3—C41.462 (8)
Hg1—I22.6592 (4)C4—C51.349 (7)
S1—C21.701 (6)C5—H5A0.9500
S1—C11.721 (6)C6—C81.491 (8)
S2—C51.708 (6)C7—H7A0.9800
S2—C61.720 (6)C7—H7B0.9800
N1—C11.309 (7)C7—H7C0.9800
N1—C31.390 (7)C8—H8A0.9800
N2—C61.304 (7)C8—H8B0.9800
N2—C41.393 (7)C8—H8C0.9800
C1—C71.475 (8)
N1—Hg1—N270.32 (15)N1—C3—C4118.4 (5)
N1—Hg1—I299.35 (11)C5—C4—N2114.2 (5)
N2—Hg1—I2114.46 (10)C5—C4—C3128.5 (5)
N1—Hg1—I1117.74 (11)N2—C4—C3117.3 (5)
N2—Hg1—I1101.61 (10)C4—C5—S2110.7 (4)
I2—Hg1—I1135.280 (14)C4—C5—H5A124.7
C2—S1—C190.4 (3)S2—C5—H5A124.7
C5—S2—C689.9 (3)N2—C6—C8124.1 (5)
C1—N1—C3112.5 (5)N2—C6—S2113.9 (4)
C1—N1—Hg1130.2 (4)C8—C6—S2122.1 (4)
C3—N1—Hg1116.5 (3)C1—C7—H7A109.5
C6—N2—C4111.4 (4)C1—C7—H7B109.5
C6—N2—Hg1131.7 (4)H7A—C7—H7B109.5
C4—N2—Hg1116.9 (3)C1—C7—H7C109.5
N1—C1—C7124.1 (5)H7A—C7—H7C109.5
N1—C1—S1113.0 (4)H7B—C7—H7C109.5
C7—C1—S1122.9 (4)C6—C8—H8A109.5
C3—C2—S1110.9 (4)C6—C8—H8B109.5
C3—C2—H2A124.5H8A—C8—H8B109.5
S1—C2—H2A124.5C6—C8—H8C109.5
C2—C3—N1113.2 (5)H8A—C8—H8C109.5
C2—C3—C4128.4 (5)H8B—C8—H8C109.5
N2—Hg1—N1—C1174.2 (5)C1—N1—C3—C20.1 (7)
I2—Hg1—N1—C161.5 (5)Hg1—N1—C3—C2171.1 (4)
I1—Hg1—N1—C1−92.7 (5)C1—N1—C3—C4180.0 (5)
N2—Hg1—N1—C35.1 (3)Hg1—N1—C3—C4−9.0 (6)
I2—Hg1—N1—C3−107.6 (4)C6—N2—C4—C50.4 (6)
I1—Hg1—N1—C398.2 (4)Hg1—N2—C4—C5176.8 (4)
N1—Hg1—N2—C6174.7 (5)C6—N2—C4—C3−179.8 (5)
I2—Hg1—N2—C6−93.8 (5)Hg1—N2—C4—C3−3.5 (6)
I1—Hg1—N2—C659.1 (5)C2—C3—C4—C58.0 (9)
N1—Hg1—N2—C4−0.7 (3)N1—C3—C4—C5−171.9 (5)
I2—Hg1—N2—C490.8 (3)C2—C3—C4—N2−171.8 (5)
I1—Hg1—N2—C4−116.3 (3)N1—C3—C4—N28.4 (7)
C3—N1—C1—C7−179.2 (5)N2—C4—C5—S20.3 (6)
Hg1—N1—C1—C711.3 (8)C3—C4—C5—S2−179.5 (4)
C3—N1—C1—S1−0.4 (6)C6—S2—C5—C4−0.6 (4)
Hg1—N1—C1—S1−169.9 (2)C4—N2—C6—C8179.5 (5)
C2—S1—C1—N10.4 (4)Hg1—N2—C6—C83.9 (8)
C2—S1—C1—C7179.3 (5)C4—N2—C6—S2−0.9 (6)
C1—S1—C2—C3−0.4 (4)Hg1—N2—C6—S2−176.6 (2)
S1—C2—C3—N10.2 (6)C5—S2—C6—N20.9 (4)
S1—C2—C3—C4−179.6 (4)C5—S2—C6—C8−179.5 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2334).

References

  • Al-Hashemi, R., Safari, N., Abedi, A., Notash, B., Amani, V. & Khavasi, H. R. (2009). J. Coord. Chem.62, 2909–2918.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848–1854.
  • Notash, B., Safari, N., Khavasi, H. R., Amani, V. & Abedi, A. (2008). J. Organomet. Chem.693, 3553–3557.
  • Safari, N., Amani, V., Abedi, A., Notash, B. & Ng, S. W. (2009). Acta Cryst. E65, m372. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305. [PMC free article] [PubMed]
  • Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography