Dichloridobis(N,N,N',N'-tetra-methyl-thio-urea-κS)mercury(II).

In the title compound, [HgCl(2)(C(5)H(12)N(2)S)(2)], the Hg(II) atom is located on a twofold rotation axis and is bonded in a distorted tetra-hedral coordination mode to two chloride ions and to two tetra-methyl-thio-urea (tmtu) mol-ecules through their S atoms. The crystal structure is stabilized by C-H⋯N and C-H⋯S hydrogen bonds.

Related literature

For background to Hg(II) complexes with thio­urea ligands, see: Ahmad et al. (2009 ▶); Chieh (1977 ▶); Lobana et al. (2008 ▶); Popovic et al. (2000 ▶, 2002 ▶). The structure of the title compound is isotypic with [Cd(tmtu)2Br2] (Nawaz et al., 2010a ▶) and [Cd(tmtu)2I2] (Nawaz et al., 2010b ▶).

Experimental

Crystal data

[HgCl2(C5H12N2S)2]

M = 535.94

Monoclinic,

a = 18.7418 (12) Å

b = 9.5920 (6) Å

c = 13.5177 (9) Å

β = 130.834 (1)°

V = 1838.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 8.88 mm−1

T = 293 K

0.29 × 0.24 × 0.11 mm

Data collection

Bruker SMART APEX area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.183, T max = 0.442

12167 measured reflections

2281 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.040

S = 1.07

2281 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.79 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536810028138/wm2376sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028138/wm2376Isup2.hkl

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

[HgCl2(C5H12N2S)2]	F(000) = 1032
Mr = 535.94	Dx = 1.936 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12167 reflections
a = 18.7418 (12) Å	θ = 2.6–28.3°
b = 9.5920 (6) Å	µ = 8.88 mm−1
c = 13.5177 (9) Å	T = 293 K
β = 130.834 (1)°	Colourless, plate
V = 1838.6 (2) Å3	0.29 × 0.24 × 0.11 mm
Z = 4

Bruker SMART APEX area detector diffractometer	2281 independent reflections
Radiation source: normal-focus sealed tube	2103 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.183, Tmax = 0.442	k = −12→12
12167 measured reflections	l = −18→18

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)] = 0.020	H-atom parameters constrained
wR(F2) = 0.040	w = 1/[σ2(Fo2) + (0.0109P)2 + 2.5249P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
2281 reflections	Δρmax = 0.72 e Å−3
92 parameters	Δρmin = −0.79 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00244 (8)

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.

	x	y	z	Uiso*/Ueq
Hg1	1.0000	0.703186 (17)	0.2500	0.04539 (7)
Cl1	1.14323 (5)	0.55933 (9)	0.34397 (8)	0.0591 (2)
S1	1.02994 (5)	0.83371 (9)	0.43697 (7)	0.04983 (18)
N1	0.91286 (18)	0.7622 (3)	0.4747 (3)	0.0482 (6)
N2	0.84430 (16)	0.8798 (3)	0.2830 (2)	0.0488 (6)
C1	0.92029 (18)	0.8240 (3)	0.3933 (3)	0.0367 (5)
C2	0.8466 (3)	0.8103 (4)	0.4900 (4)	0.0704 (10)
H2A	0.8192	0.8971	0.4446	0.106*
H2B	0.8793	0.8232	0.5812	0.106*
H2C	0.7977	0.7421	0.4542	0.106*
C3	0.9842 (3)	0.6647 (4)	0.5756 (4)	0.0769 (11)
H3A	1.0131	0.6182	0.5468	0.115*
H3B	0.9549	0.5970	0.5914	0.115*
H3C	1.0313	0.7149	0.6548	0.115*
C4	0.7491 (2)	0.8240 (5)	0.2114 (4)	0.0802 (12)
H4A	0.7531	0.7329	0.2441	0.120*
H4B	0.7174	0.8179	0.1200	0.120*
H4C	0.7144	0.8847	0.2231	0.120*
C5	0.8518 (3)	0.9798 (4)	0.2094 (4)	0.0774 (11)
H5A	0.9121	1.0250	0.2669	0.116*
H5B	0.8027	1.0483	0.1711	0.116*
H5C	0.8454	0.9323	0.1414	0.116*

	U11	U22	U33	U12	U13	U23
Hg1	0.05014 (10)	0.04849 (10)	0.05259 (11)	0.000	0.04018 (9)	0.000
Cl1	0.0519 (4)	0.0599 (5)	0.0652 (5)	0.0126 (3)	0.0381 (4)	0.0065 (4)
S1	0.0386 (3)	0.0716 (5)	0.0453 (4)	−0.0091 (3)	0.0300 (3)	−0.0142 (3)
N1	0.0611 (15)	0.0488 (13)	0.0566 (14)	0.0005 (11)	0.0480 (13)	0.0002 (11)
N2	0.0439 (13)	0.0560 (15)	0.0465 (13)	0.0051 (11)	0.0295 (11)	0.0020 (11)
C1	0.0415 (13)	0.0364 (13)	0.0415 (13)	−0.0023 (10)	0.0312 (12)	−0.0061 (10)
C2	0.085 (2)	0.081 (3)	0.092 (3)	−0.011 (2)	0.078 (2)	−0.014 (2)
C3	0.098 (3)	0.070 (2)	0.076 (2)	0.015 (2)	0.063 (2)	0.024 (2)
C4	0.0387 (17)	0.116 (3)	0.070 (2)	−0.0013 (18)	0.0292 (17)	−0.015 (2)
C5	0.088 (3)	0.081 (3)	0.069 (2)	0.027 (2)	0.054 (2)	0.029 (2)

Hg1—Cl1i	2.5028 (8)	C2—H2B	0.9600
Hg1—Cl1	2.5028 (8)	C2—H2C	0.9600
Hg1—S1	2.5329 (7)	C3—H3A	0.9600
Hg1—S1i	2.5329 (7)	C3—H3B	0.9600
S1—C1	1.730 (3)	C3—H3C	0.9600
N1—C1	1.336 (3)	C4—H4A	0.9600
N1—C2	1.460 (4)	C4—H4B	0.9600
N1—C3	1.461 (4)	C4—H4C	0.9600
N2—C1	1.327 (3)	C5—H5A	0.9600
N2—C5	1.453 (4)	C5—H5B	0.9600
N2—C4	1.466 (4)	C5—H5C	0.9600
C2—H2A	0.9600
Cl1i—Hg1—Cl1	113.08 (4)	H2A—C2—H2C	109.5
Cl1i—Hg1—S1	104.08 (3)	H2B—C2—H2C	109.5
Cl1—Hg1—S1	107.56 (3)	N1—C3—H3A	109.5
Cl1i—Hg1—S1i	107.56 (3)	N1—C3—H3B	109.5
Cl1—Hg1—S1i	104.08 (3)	H3A—C3—H3B	109.5
S1—Hg1—S1i	120.75 (4)	N1—C3—H3C	109.5
C1—S1—Hg1	101.20 (9)	H3A—C3—H3C	109.5
C1—N1—C2	122.2 (3)	H3B—C3—H3C	109.5
C1—N1—C3	121.9 (3)	N2—C4—H4A	109.5
C2—N1—C3	114.4 (3)	N2—C4—H4B	109.5
C1—N2—C5	121.5 (3)	H4A—C4—H4B	109.5
C1—N2—C4	122.9 (3)	N2—C4—H4C	109.5
C5—N2—C4	114.2 (3)	H4A—C4—H4C	109.5
N2—C1—N1	119.5 (2)	H4B—C4—H4C	109.5
N2—C1—S1	121.6 (2)	N2—C5—H5A	109.5
N1—C1—S1	118.9 (2)	N2—C5—H5B	109.5
N1—C2—H2A	109.5	H5A—C5—H5B	109.5
N1—C2—H2B	109.5	N2—C5—H5C	109.5
H2A—C2—H2B	109.5	H5A—C5—H5C	109.5
N1—C2—H2C	109.5	H5B—C5—H5C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N2	0.96	2.52	2.849 (6)	100
C3—H3A···S1	0.96	2.68	2.996 (6)	100
C5—H5A···S1	0.96	2.62	3.024 (5)	105

Table 1

Selected bond lengths (Å)

Hg1—Cl1	2.5028 (8)
Hg1—S1	2.5329 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯N2	0.96	2.52	2.849 (6)	100
C3—H3A⋯S1	0.96	2.68	2.996 (6)	100
C5—H5A⋯S1	0.96	2.62	3.024 (5)	105