(2,2'-Dimethyl-4,4'-bi-1,3-thia-zole-κN,N')bis(thio-cyanato-κS)mercury(II).

The Hg(II) atom in the title compound, [Hg(SCN)(2)(C(8)H(8)N(2)S(2))], is chelated by the bidentate heterocycle through the N atoms and is coordinated by the S atoms of two thiocyanate anions, resulting in a considerably distorted tetra-hedral coordination geometry.

Related literature

There are several examples of mercuric thio­cyanate–α,α′-dimine type of adducts which exist as four-coordinate, tetra­hedral mol­ecules. For the 4,4′,5,5′-tetra­methyl-2,2′-biimidazole adduct, see: Mahjoub et al. (2003 ▶); Morsali (2006 ▶). For the 2,2′-diamino-4,4′-bithia­zole adduct, see: Morsali et al. (2003 ▶). For the 2,2′-biquinoline adduct, see: Morsali et al. (2004 ▶); Ramazani et al. (2004 ▶). For the 2,2′-diphenyl-4,4′-bithia­zole adduct, see: Mahjoub & Morsali (2003 ▶).

Experimental

Crystal data

[Hg(NCS)2(C8H8N2S2)]

M = 513.03

Monoclinic,

a = 17.3764 (3) Å

b = 12.0534 (2) Å

c = 7.0601 (1) Å

β = 100.676 (1)°

V = 1453.10 (4) Å3

Z = 4

Mo Kα radiation

μ = 11.16 mm−1

T = 118 K

0.22 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.274, T max = 0.640

10030 measured reflections

3330 independent reflections

2982 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.054

S = 1.04

3330 reflections

174 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −1.32 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006904/xu2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006904/xu2488Isup2.hkl

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

[Hg(NCS)2(C8H8N2S2)]	F(000) = 960
Mr = 513.03	Dx = 2.345 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4390 reflections
a = 17.3764 (3) Å	θ = 2.4–28.3°
b = 12.0534 (2) Å	µ = 11.16 mm−1
c = 7.0601 (1) Å	T = 118 K
β = 100.676 (1)°	Block, colorless
V = 1453.10 (4) Å3	0.22 × 0.06 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	3330 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.274, Tmax = 0.640	k = −15→15
10030 measured reflections	l = −8→9

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) = 0.054	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0213P)2 + 2.1611P] where P = (Fo2 + 2Fc2)/3
3330 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 1.17 e Å−3
0 restraints	Δρmin = −1.31 e Å−3

	x	y	z	Uiso*/Ueq
Hg1	0.272849 (8)	0.578858 (12)	0.74895 (2)	0.01665 (6)
S1	0.37984 (5)	0.20867 (8)	0.65772 (15)	0.0156 (2)
S2	0.03250 (6)	0.34937 (8)	0.73374 (16)	0.0192 (2)
S3	0.34553 (7)	0.58014 (9)	1.07522 (18)	0.0287 (3)
S4	0.20772 (7)	0.68035 (9)	0.46884 (17)	0.0241 (2)
N1	0.30803 (18)	0.3905 (3)	0.6768 (5)	0.0132 (7)
N2	0.16170 (18)	0.4504 (3)	0.7495 (5)	0.0147 (7)
N3	0.4178 (2)	0.7908 (3)	1.1095 (6)	0.0317 (9)
N4	0.1421 (2)	0.4986 (3)	0.2409 (6)	0.0270 (8)
C1	0.4453 (2)	0.4223 (3)	0.6435 (7)	0.0221 (9)
H1A	0.4274	0.4900	0.5719	0.033*
H1B	0.4807	0.3815	0.5755	0.033*
H1C	0.4730	0.4421	0.7729	0.033*
C2	0.3765 (2)	0.3514 (3)	0.6592 (6)	0.0149 (8)
C3	0.2837 (2)	0.2028 (3)	0.6837 (6)	0.0148 (8)
H3	0.2549	0.1364	0.6912	0.018*
C4	0.2545 (2)	0.3082 (3)	0.6921 (6)	0.0128 (8)
C5	0.1758 (2)	0.3395 (3)	0.7151 (5)	0.0124 (7)
C6	0.1123 (2)	0.2727 (3)	0.7042 (6)	0.0163 (8)
H6	0.1121	0.1949	0.6834	0.020*
C7	0.0890 (2)	0.4686 (3)	0.7608 (6)	0.0158 (8)
C8	0.0558 (2)	0.5793 (3)	0.7950 (7)	0.0207 (9)
H8A	0.0831	0.6090	0.9186	0.031*
H8B	−0.0001	0.5716	0.7980	0.031*
H8C	0.0626	0.6301	0.6910	0.031*
C9	0.3879 (2)	0.7054 (3)	1.0890 (6)	0.0201 (9)
C10	0.1696 (2)	0.5709 (3)	0.3354 (6)	0.0188 (9)

	U11	U22	U33	U12	U13	U23
Hg1	0.01515 (8)	0.01369 (8)	0.01971 (10)	−0.00045 (5)	−0.00039 (6)	−0.00147 (6)
S1	0.0154 (5)	0.0132 (4)	0.0188 (5)	0.0017 (3)	0.0049 (4)	−0.0005 (4)
S2	0.0120 (5)	0.0188 (5)	0.0271 (6)	−0.0016 (4)	0.0043 (4)	0.0004 (4)
S3	0.0367 (6)	0.0183 (5)	0.0249 (6)	−0.0089 (4)	−0.0108 (5)	0.0058 (5)
S4	0.0294 (6)	0.0140 (5)	0.0254 (6)	−0.0040 (4)	−0.0044 (5)	0.0029 (4)
N1	0.0118 (16)	0.0143 (15)	0.0133 (17)	−0.0004 (12)	0.0023 (12)	−0.0001 (13)
N2	0.0144 (16)	0.0150 (16)	0.0147 (18)	−0.0021 (12)	0.0029 (13)	0.0006 (13)
N3	0.036 (2)	0.025 (2)	0.031 (2)	−0.0093 (17)	−0.0018 (18)	−0.0027 (18)
N4	0.028 (2)	0.0228 (19)	0.027 (2)	−0.0006 (16)	−0.0031 (16)	−0.0014 (17)
C1	0.0134 (19)	0.018 (2)	0.035 (3)	0.0010 (15)	0.0055 (18)	0.0017 (19)
C2	0.0156 (19)	0.0140 (18)	0.014 (2)	0.0022 (14)	0.0011 (15)	−0.0001 (16)
C3	0.0145 (19)	0.0154 (19)	0.015 (2)	−0.0006 (14)	0.0037 (15)	−0.0014 (16)
C4	0.0134 (18)	0.0146 (18)	0.0099 (19)	0.0005 (14)	0.0013 (14)	0.0004 (15)
C5	0.0137 (18)	0.0140 (18)	0.0092 (19)	0.0008 (14)	0.0010 (14)	0.0022 (15)
C6	0.0129 (18)	0.0169 (19)	0.020 (2)	0.0005 (14)	0.0050 (15)	−0.0002 (17)
C7	0.0174 (19)	0.0133 (18)	0.017 (2)	0.0022 (15)	0.0037 (15)	0.0009 (16)
C8	0.018 (2)	0.018 (2)	0.027 (2)	0.0052 (16)	0.0064 (17)	−0.0023 (18)
C9	0.017 (2)	0.021 (2)	0.022 (2)	0.0007 (16)	0.0020 (16)	−0.0014 (18)
C10	0.0113 (19)	0.019 (2)	0.026 (2)	0.0012 (15)	0.0019 (16)	0.0042 (18)

Hg1—S3	2.413 (1)	N4—C10	1.146 (6)
Hg1—S4	2.421 (1)	C1—C2	1.490 (5)
Hg1—N1	2.430 (3)	C1—H1A	0.9800
Hg1—N2	2.476 (3)	C1—H1B	0.9800
S1—C2	1.721 (4)	C1—H1C	0.9800
S1—C3	1.716 (4)	C3—C4	1.374 (5)
S2—C6	1.711 (4)	C3—H3	0.9500
S2—C7	1.731 (4)	C4—C5	1.455 (5)
S3—C9	1.675 (4)	C5—C6	1.356 (5)
S4—C10	1.684 (4)	C6—H6	0.9500
N1—C2	1.308 (5)	C7—C8	1.491 (5)
N1—C4	1.379 (5)	C8—H8A	0.9800
N2—C7	1.299 (5)	C8—H8B	0.9800
N2—C5	1.389 (5)	C8—H8C	0.9800
N3—C9	1.150 (5)
S3—Hg1—S4	149.25 (4)	C1—C2—S1	123.0 (3)
S3—Hg1—N1	95.66 (8)	C4—C3—S1	110.0 (3)
S3—Hg1—N2	105.84 (8)	C4—C3—H3	125.0
S4—Hg1—N1	113.49 (8)	S1—C3—H3	125.0
S4—Hg1—N2	94.04 (8)	C3—C4—N1	113.7 (3)
N1—Hg1—N2	69.1 (1)	C3—C4—C5	127.4 (3)
C2—S1—C3	90.37 (19)	N1—C4—C5	118.9 (3)
C6—S2—C7	90.33 (19)	C6—C5—N2	114.4 (3)
C9—S3—Hg1	102.01 (16)	C6—C5—C4	127.7 (4)
C10—S4—Hg1	97.89 (15)	N2—C5—C4	117.9 (3)
C2—N1—C4	112.8 (3)	C5—C6—S2	110.0 (3)
C2—N1—Hg1	128.7 (3)	C5—C6—H6	125.0
C4—N1—Hg1	117.1 (2)	S2—C6—H6	125.0
C7—N2—C5	112.2 (3)	N2—C7—C8	124.8 (4)
C7—N2—Hg1	131.5 (3)	N2—C7—S2	113.0 (3)
C5—N2—Hg1	116.0 (2)	C8—C7—S2	122.2 (3)
C2—C1—H1A	109.5	C7—C8—H8A	109.5
C2—C1—H1B	109.5	C7—C8—H8B	109.5
H1A—C1—H1B	109.5	H8A—C8—H8B	109.5
C2—C1—H1C	109.5	C7—C8—H8C	109.5
H1A—C1—H1C	109.5	H8A—C8—H8C	109.5
H1B—C1—H1C	109.5	H8B—C8—H8C	109.5
N1—C2—C1	123.8 (3)	N3—C9—S3	176.2 (4)
N1—C2—S1	113.1 (3)	N4—C10—S4	177.9 (4)
S4—Hg1—S3—C9	−25.10 (19)	C2—S1—C3—C4	0.0 (3)
N1—Hg1—S3—C9	136.75 (17)	S1—C3—C4—N1	0.4 (4)
N2—Hg1—S3—C9	−153.45 (17)	S1—C3—C4—C5	−179.5 (3)
S3—Hg1—S4—C10	−173.66 (15)	C2—N1—C4—C3	−0.7 (5)
N1—Hg1—S4—C10	26.10 (17)	Hg1—N1—C4—C3	−168.8 (3)
N2—Hg1—S4—C10	−42.80 (16)	C2—N1—C4—C5	179.2 (3)
S3—Hg1—N1—C2	−67.8 (3)	Hg1—N1—C4—C5	11.1 (4)
S4—Hg1—N1—C2	102.2 (3)	C7—N2—C5—C6	−1.3 (5)
N2—Hg1—N1—C2	−172.6 (4)	Hg1—N2—C5—C6	−176.0 (3)
S3—Hg1—N1—C4	98.2 (3)	C7—N2—C5—C4	177.8 (3)
S4—Hg1—N1—C4	−91.8 (3)	Hg1—N2—C5—C4	3.1 (4)
N2—Hg1—N1—C4	−6.6 (3)	C3—C4—C5—C6	−10.6 (7)
S3—Hg1—N2—C7	98.2 (4)	N1—C4—C5—C6	169.5 (4)
S4—Hg1—N2—C7	−58.1 (4)	C3—C4—C5—N2	170.4 (4)
N1—Hg1—N2—C7	−171.8 (4)	N1—C4—C5—N2	−9.5 (5)
S3—Hg1—N2—C5	−88.4 (3)	N2—C5—C6—S2	0.9 (4)
S4—Hg1—N2—C5	115.3 (3)	C4—C5—C6—S2	−178.1 (3)
N1—Hg1—N2—C5	1.7 (2)	C7—S2—C6—C5	−0.3 (3)
C4—N1—C2—C1	−178.9 (4)	C5—N2—C7—C8	−179.5 (4)
Hg1—N1—C2—C1	−12.4 (6)	Hg1—N2—C7—C8	−5.8 (6)
C4—N1—C2—S1	0.6 (4)	C5—N2—C7—S2	1.0 (4)
Hg1—N1—C2—S1	167.11 (18)	Hg1—N2—C7—S2	174.69 (19)
C3—S1—C2—N1	−0.3 (3)	C6—S2—C7—N2	−0.4 (3)
C3—S1—C2—C1	179.2 (4)	C6—S2—C7—C8	−179.9 (4)

Hg1—S3	2.413 (1)
Hg1—S4	2.421 (1)
Hg1—N1	2.430 (3)
Hg1—N2	2.476 (3)

S3—Hg1—S4	149.25 (4)
S3—Hg1—N1	95.66 (8)
S3—Hg1—N2	105.84 (8)
S4—Hg1—N1	113.49 (8)
S4—Hg1—N2	94.04 (8)
N1—Hg1—N2	69.1 (1)