Bis(1,3-dibutylthiourea)dicyanido-mercury(II).

In the title compound, [Hg(CN)(2)(C(9)H(20)N(2)S)(2)], the Hg atom lies on a twofold rotation axis. There is only half a mol-ecule in the asymmetric unit. The Hg atom has a distorted tetra-hedral coordination involving the S atoms of two 1-butyl-3-propyl-thio-urea groups and the C atoms of the two CN(-) anions. In the crystal packing, adjacent mol-ecules are connected by inter-molecular N-H⋯N and N-H⋯S hydrogen bonds, forming infinite chains in three dimensions.

Related literature

For the coordination chemistry of thio­urea-type ligands, see: Nadeem et al. (2009 ▶, 2008 ▶); Zoufalá et al. (2007 ▶); Khan et al. (2007 ▶); Hanif et al. (2007 ▶); Fuks et al. (2005 ▶); Moro et al. (2009 ▶); Matesanz & Souza (2007 ▶). For crystallographic reports about mercury(II) complexes containing thio­amides, see: Popovic et al. (2000 ▶, 2002 ▶); Pavlović et al. (2000 ▶); Jiang et al. (2001 ▶); Wu et al. (2004 ▶). For the spectroscopy and structural chemistry of cyanide complexes of silver(I) and gold(I) with thio­nes, see: Hanif et al. (2007 ▶); Wu et al. (2004 ▶); Ahmad, Isab & Ashraf (2002 ▶); Ahmad, Isab & Perzanowski (2002 ▶); Ashraf et al. (2002 ▶); Ahmad & Isab (2001 ▶); Ahmad (2004 ▶).

Experimental

Crystal data

[Hg(CN)2(C9H20N2S)2]

M = 629.31

Monoclinic,

a = 17.4692 (3) Å

b = 9.5928 (2) Å

c = 17.4699 (4) Å

β = 111.540 (1)°

V = 2723.12 (10) Å3

Z = 4

Mo Kα radiation

μ = 5.82 mm−1

T = 296 K

0.14 × 0.15 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: none

15120 measured reflections

3372 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.044

S = 1.02

3372 reflections

134 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.72 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035594/bt5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035594/bt5052Isup2.hkl

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

[Hg(CN)2(C9H20N2S)2]	F(000) = 1256
Mr = 629.31	Dx = 1.535 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6609 reflections
a = 17.4692 (3) Å	θ = 2.5–27.2°
b = 9.5928 (2) Å	µ = 5.82 mm−1
c = 17.4699 (4) Å	T = 296 K
β = 111.540 (1)°	Irregular, white
V = 2723.12 (10) Å3	0.17 × 0.15 × 0.14 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	2918 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.032
graphite	θmax = 28.3°, θmin = 2.5°
φ and ω scans	h = −23→23
15120 measured reflections	k = −12→12
3372 independent reflections	l = −20→23

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.044	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0211P)2], where P = (Fo2 + 2Fc2)/3
3372 reflections	(Δ/σ)max = 0.001
134 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	1.00000	0.20478 (1)	0.75000	0.0405 (1)
S1	1.08516 (3)	0.39691 (7)	0.86634 (4)	0.0414 (2)
N1	0.86048 (15)	0.1224 (3)	0.81955 (17)	0.0718 (10)
N2	1.11488 (12)	0.5094 (2)	0.74219 (12)	0.0422 (7)
N3	1.22801 (11)	0.4758 (2)	0.85840 (12)	0.0411 (7)
C1	0.91098 (16)	0.1498 (3)	0.79668 (17)	0.0475 (9)
C2	1.14750 (13)	0.4655 (2)	0.81878 (15)	0.0341 (7)
C3	1.16093 (17)	0.5591 (3)	0.69240 (17)	0.0548 (10)
C4	1.10347 (17)	0.6051 (3)	0.60900 (17)	0.0534 (10)
C5	1.0548 (2)	0.7334 (4)	0.6094 (2)	0.0633 (12)
C6	0.9979 (3)	0.7767 (4)	0.5243 (3)	0.0875 (17)
C7	1.27223 (15)	0.4387 (3)	0.94375 (16)	0.0441 (8)
C8	1.27906 (17)	0.5571 (3)	1.00242 (16)	0.0473 (9)
C9	1.3311 (2)	0.5232 (3)	1.09034 (17)	0.0586 (11)
C10	1.3434 (3)	0.6466 (4)	1.1477 (2)	0.0795 (14)
H2	1.06210	0.50880	0.71950	0.0510*
H3	1.25650	0.50710	0.83120	0.0490*
H3A	1.19600	0.48500	0.68630	0.0660*
H3B	1.19580	0.63660	0.72020	0.0660*
H4A	1.13530	0.62230	0.57470	0.0640*
H4B	1.06550	0.52970	0.58410	0.0640*
H5A	1.09240	0.80930	0.63420	0.0760*
H5B	1.02240	0.71650	0.64330	0.0760*
H6A	1.02880	0.78550	0.48910	0.1310*
H6B	0.97300	0.86460	0.52750	0.1310*
H6C	0.95580	0.70750	0.50240	0.1310*
H7A	1.32710	0.40780	0.95010	0.0530*
H7B	1.24430	0.36120	0.95810	0.0530*
H8A	1.22430	0.58250	0.99950	0.0570*
H8B	1.30250	0.63730	0.98510	0.0570*
H9A	1.38450	0.49040	1.09270	0.0700*
H9B	1.30520	0.44820	1.10920	0.0700*
H10A	1.36760	0.72220	1.12850	0.1190*
H10B	1.37910	0.62040	1.20210	0.1190*
H10C	1.29110	0.67540	1.14870	0.1190*

	U11	U22	U33	U12	U13	U23
Hg1	0.0323 (1)	0.0459 (1)	0.0478 (1)	0.0000	0.0199 (1)	0.0000
S1	0.0359 (3)	0.0566 (4)	0.0340 (3)	−0.0115 (3)	0.0154 (3)	−0.0005 (3)
N1	0.0516 (14)	0.104 (2)	0.0668 (17)	−0.0297 (15)	0.0300 (13)	−0.0046 (17)
N2	0.0326 (10)	0.0594 (14)	0.0352 (12)	−0.0068 (9)	0.0133 (9)	0.0057 (11)
N3	0.0313 (10)	0.0545 (13)	0.0383 (12)	−0.0043 (9)	0.0136 (9)	0.0051 (10)
C1	0.0385 (13)	0.0553 (16)	0.0463 (16)	−0.0125 (12)	0.0126 (12)	−0.0037 (14)
C2	0.0330 (11)	0.0369 (13)	0.0340 (14)	−0.0030 (9)	0.0142 (10)	−0.0015 (11)
C3	0.0473 (15)	0.076 (2)	0.0491 (17)	−0.0018 (14)	0.0270 (14)	0.0144 (15)
C4	0.0563 (16)	0.069 (2)	0.0396 (16)	−0.0019 (14)	0.0232 (13)	0.0039 (15)
C5	0.076 (2)	0.066 (2)	0.052 (2)	0.0065 (17)	0.0285 (17)	0.0103 (16)
C6	0.084 (3)	0.101 (3)	0.074 (3)	0.026 (2)	0.025 (2)	0.020 (2)
C7	0.0353 (12)	0.0476 (15)	0.0446 (16)	0.0040 (11)	0.0089 (11)	0.0054 (13)
C8	0.0477 (14)	0.0466 (15)	0.0427 (16)	0.0038 (12)	0.0110 (12)	0.0064 (13)
C9	0.0665 (19)	0.0565 (19)	0.0433 (17)	0.0044 (15)	0.0090 (15)	0.0050 (15)
C10	0.107 (3)	0.066 (2)	0.051 (2)	−0.005 (2)	0.012 (2)	−0.0008 (19)

Hg1—S1	2.7424 (7)	C3—H3A	0.9700
Hg1—C1	2.072 (3)	C3—H3B	0.9700
Hg1—S1i	2.7424 (7)	C4—H4A	0.9700
Hg1—C1i	2.072 (3)	C4—H4B	0.9700
S1—C2	1.724 (2)	C5—H5A	0.9700
N1—C1	1.125 (4)	C5—H5B	0.9700
N2—C2	1.316 (3)	C6—H6A	0.9600
N2—C3	1.465 (4)	C6—H6B	0.9600
N3—C2	1.324 (3)	C6—H6C	0.9600
N3—C7	1.449 (3)	C7—H7A	0.9700
N2—H2	0.8600	C7—H7B	0.9700
N3—H3	0.8600	C8—H8A	0.9700
C3—C4	1.500 (4)	C8—H8B	0.9700
C4—C5	1.497 (5)	C9—H9A	0.9700
C5—C6	1.512 (6)	C9—H9B	0.9700
C7—C8	1.505 (4)	C10—H10A	0.9600
C8—C9	1.505 (4)	C10—H10B	0.9600
C9—C10	1.514 (5)	C10—H10C	0.9600
S1···C1	3.693 (3)	H3A···N3	2.8500
S1···C8	3.684 (3)	H3A···H3	2.3700
S1···N2i	3.479 (2)	H3A···H10Cvi	2.5200
S1···H7B	2.6700	H3B···N3	2.7400
S1···H2i	2.6800	H3B···H3	2.2200
S1···H6Aii	3.1900	H3B···H5A	2.5000
N1···N3iii	2.991 (3)	H3B···N1iv	2.7600
N1···C3iii	3.431 (4)	H4A···H6A	2.4700
N2···S1i	3.479 (2)	H4B···H2	2.4000
N3···N1iv	2.991 (3)	H4B···H6C	2.5700
N1···H3Biii	2.7600	H5A···H3B	2.5000
N1···H3iii	2.2000	H5A···H7Avii	2.5600
N2···H5B	2.7400	H5B···N2	2.7400
N3···H3A	2.8500	H5B···H2	2.3500
N3···H3B	2.7400	H6A···H4A	2.4700
C1···S1	3.693 (3)	H6A···S1vi	3.1900
C1···C2i	3.574 (4)	H6C···H4B	2.5700
C3···N1iv	3.431 (4)	H7A···H9A	2.4500
C8···S1	3.684 (3)	H7A···H5Aviii	2.5600
C1···H10Bv	3.0100	H7B···S1	2.6700
C3···H3	2.4400	H7B···H9B	2.6000
C5···H2	2.8600	H7B···H7Bix	2.5500
H2···C5	2.8600	H8A···H10C	2.5900
H2···H4B	2.4000	H8B···H10A	2.4800
H2···H5B	2.3500	H9A···H7A	2.4500
H2···S1i	2.6800	H9B···H7B	2.6000
H3···C3	2.4400	H10A···H8B	2.4800
H3···H3A	2.3700	H10B···C1x	3.0100
H3···H3B	2.2200	H10C···H8A	2.5900
H3···N1iv	2.2000	H10C···H3Aii	2.5200
S1—Hg1—C1	99.25 (8)	C4—C5—H5A	109.00
S1—Hg1—S1i	95.55 (2)	C4—C5—H5B	109.00
S1—Hg1—C1i	100.45 (8)	C6—C5—H5A	109.00
S1i—Hg1—C1	100.45 (8)	C6—C5—H5B	109.00
C1—Hg1—C1i	150.51 (11)	H5A—C5—H5B	108.00
S1i—Hg1—C1i	99.25 (8)	C5—C6—H6A	109.00
Hg1—S1—C2	99.56 (8)	C5—C6—H6B	109.00
C2—N2—C3	125.5 (2)	C5—C6—H6C	109.00
C2—N3—C7	125.6 (2)	H6A—C6—H6B	109.00
C2—N2—H2	117.00	H6A—C6—H6C	110.00
C3—N2—H2	117.00	H6B—C6—H6C	109.00
C2—N3—H3	117.00	N3—C7—H7A	109.00
C7—N3—H3	117.00	N3—C7—H7B	109.00
Hg1—C1—N1	177.4 (3)	C8—C7—H7A	109.00
S1—C2—N2	119.84 (19)	C8—C7—H7B	109.00
S1—C2—N3	120.95 (18)	H7A—C7—H7B	108.00
N2—C2—N3	119.2 (2)	C7—C8—H8A	109.00
N2—C3—C4	110.8 (2)	C7—C8—H8B	109.00
C3—C4—C5	114.6 (2)	C9—C8—H8A	109.00
C4—C5—C6	113.0 (3)	C9—C8—H8B	109.00
N3—C7—C8	113.2 (2)	H8A—C8—H8B	108.00
C7—C8—C9	113.5 (2)	C8—C9—H9A	109.00
C8—C9—C10	113.1 (3)	C8—C9—H9B	109.00
N2—C3—H3A	109.00	C10—C9—H9A	109.00
N2—C3—H3B	109.00	C10—C9—H9B	109.00
C4—C3—H3A	109.00	H9A—C9—H9B	108.00
C4—C3—H3B	109.00	C9—C10—H10A	109.00
H3A—C3—H3B	108.00	C9—C10—H10B	109.00
C3—C4—H4A	109.00	C9—C10—H10C	109.00
C3—C4—H4B	109.00	H10A—C10—H10B	110.00
C5—C4—H4A	109.00	H10A—C10—H10C	109.00
C5—C4—H4B	109.00	H10B—C10—H10C	110.00
H4A—C4—H4B	108.00
C1—Hg1—S1—C2	−169.87 (11)	C7—N3—C2—S1	−2.8 (3)
S1i—Hg1—S1—C2	−68.30 (8)	C7—N3—C2—N2	176.7 (2)
C1i—Hg1—S1—C2	32.19 (11)	C2—N3—C7—C8	−88.9 (3)
Hg1—S1—C2—N2	51.24 (18)	N2—C3—C4—C5	67.9 (3)
Hg1—S1—C2—N3	−129.28 (17)	C3—C4—C5—C6	179.8 (3)
C3—N2—C2—S1	−174.74 (19)	N3—C7—C8—C9	−175.0 (2)
C3—N2—C2—N3	5.8 (3)	C7—C8—C9—C10	175.2 (3)
C2—N2—C3—C4	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.68	3.479 (2)	155
N3—H3···N1iv	0.86	2.20	2.991 (3)	153
C7—H7B···S1	0.97	2.67	3.070 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.68	3.479 (2)	155
N3—H3⋯N1ii	0.86	2.20	2.991 (3)	153
C7—H7B⋯S1	0.97	2.67	3.070 (3)	105

Symmetry codes: (i) ; (ii) .