Crystal structure of {bis-[(1H-benzimid-azol-2-yl-κN (3))meth-yl]sulfane}dichloridomercury(II).

In the asymmetric unit of the title compound, [HgCl2(C16H14N4S)], the Hg(II) cation is linked to two Cl atoms and two imidazole N atoms of the chelating bis-[(1H-benzimidazol-2-yl)meth-yl]sulfane ligand, forming a slightly distorted tetra-hedral environment. The substitued imidazole rings of the ligand are almost perfectly planar [with maximum deviations of 0.017 (3) and 0.012 (3) Å] and form a dihedral angle of 42.51 (5)°. The crystal packing can be described as alternating layers parallel to (010). In this arrangement, N-H⋯Cl hydrogen bonds between the N-H groups of the benzimidazole moieties and chloride ligands are responsible for the formation of the chain-like packing pattern along [010] exhibiting a C(6) graph-set motif.

Related literature

For the synthesis and applications of benzimiazole derivatives, see: Tiwari et al. (2007 ▸); Gowda et al. (2009 ▸); Sondhi et al., (2010 ▸). For the coordination of benzimiazole derivatives, see: Téllez et al. (2008 ▸); Sundberg & Martin (1974 ▸); Reedijk (1987 ▸).

Experimental

Crystal data

[HgCl2(C16H14N4S)]

M = 565.86

Orthorhombic,

a = 13.8558 (3) Å

b = 15.4983 (4) Å

c = 16.1108 (4) Å

V = 3459.66 (14) Å3

Z = 8

Mo Kα radiation

μ = 9.33 mm−1

T = 295 K

0.16 × 0.11 × 0.09 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▸) T min = 0.646, T max = 0.746

78309 measured reflections

5594 independent reflections

4351 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.046

S = 1.01

5594 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.93 e Å−3

Data collection: APEX2 (Bruker, 2011 ▸); cell refinement: SAINT (Bruker, 2011 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▸); program(s) used to refine structure: SHELXT (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg & Berndt, 2001 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S205698901502349X/im2475sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901502349X/im2475Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S205698901502349X/im2475fig1.tif

The mol­ecular structure of the title compound with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Click here for additional data file.

b b a . DOI: 10.1107/S205698901502349X/im2475fig2.tif

Alternating layers parallel to (010) plane of (I) at b = 1/4 and b = 3/4, viewed down the a axis.

CCDC reference: 1440754

Additional supporting information: crystallographic information; 3D view; checkCIF report

[HgCl2(C16H14N4S)]	Dx = 2.173 Mg m−3
Mr = 565.86	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9958 reflections
a = 13.8558 (3) Å	θ = 2.3–29.6°
b = 15.4983 (4) Å	µ = 9.33 mm−1
c = 16.1108 (4) Å	T = 295 K
V = 3459.66 (14) Å3	Prism, colorless
Z = 8	0.16 × 0.11 × 0.09 mm
F(000) = 2144

Bruker APEXII diffractometer	5594 independent reflections
Radiation source: Enraf Nonius FR590	4351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
CCD rotation images, thick slices scans	θmax = 31.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −20→20
Tmin = 0.646, Tmax = 0.746	k = −22→22
78309 measured reflections	l = −22→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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0162P)2 + 4.119P] where P = (Fo2 + 2Fc2)/3
5594 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.93 e Å−3

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
C1	−0.02521 (16)	0.28013 (15)	0.20752 (14)	0.0275 (5)
C2	−0.08439 (18)	0.21383 (18)	0.17932 (16)	0.0350 (5)
H2	−0.0882	0.1613	0.207	0.042*
C3	−0.13721 (19)	0.2296 (2)	0.10828 (17)	0.0425 (7)
H3	−0.1779	0.1868	0.088	0.051*
C4	−0.1311 (2)	0.3079 (2)	0.06612 (17)	0.0447 (7)
H4	−0.1673	0.3155	0.0181	0.054*
C5	−0.07323 (19)	0.3743 (2)	0.09337 (17)	0.0404 (6)
H5	−0.0696	0.4266	0.0652	0.048*
C6	−0.02053 (17)	0.35897 (16)	0.16529 (15)	0.0289 (5)
C7	0.07692 (16)	0.36125 (15)	0.27412 (15)	0.0272 (5)
C8	0.14891 (18)	0.39298 (16)	0.33483 (16)	0.0332 (5)
H8A	0.193	0.4319	0.3068	0.04*
H8B	0.1862	0.3444	0.3551	0.04*
C9	0.0330 (2)	0.36181 (17)	0.47575 (17)	0.0355 (5)
H9A	−0.0062	0.3861	0.5198	0.043*
H9B	−0.0101	0.3339	0.4366	0.043*
C10	0.09852 (17)	0.29578 (15)	0.51189 (14)	0.0272 (4)
C11	0.17866 (16)	0.17664 (14)	0.53263 (14)	0.0247 (4)
C12	0.21845 (18)	0.09428 (16)	0.52899 (16)	0.0321 (5)
H12	0.2047	0.0568	0.4855	0.039*
C13	0.27933 (19)	0.07089 (18)	0.59296 (17)	0.0388 (6)
H13	0.3068	0.0161	0.5925	0.047*
C14	0.30100 (19)	0.12684 (19)	0.65845 (17)	0.0394 (6)
H14	0.3426	0.1085	0.7001	0.047*
C15	0.26224 (19)	0.20829 (18)	0.66267 (16)	0.0362 (6)
H15	0.277	0.2458	0.7059	0.043*
C16	0.19957 (16)	0.23173 (15)	0.59886 (14)	0.0274 (5)
N1	0.03651 (14)	0.28386 (12)	0.27585 (12)	0.0272 (4)
N2	0.11618 (14)	0.21920 (12)	0.47882 (12)	0.0268 (4)
N3	0.04426 (15)	0.40839 (13)	0.20965 (13)	0.0311 (4)
H3N	0.061	0.4605	0.1981	0.037*
N4	0.14764 (15)	0.30614 (13)	0.58354 (12)	0.0310 (4)
H4N	0.1468	0.3514	0.6144	0.037*
S1	0.09600 (6)	0.44882 (4)	0.42297 (4)	0.04249 (16)
Cl1	−0.09138 (5)	0.08943 (4)	0.37366 (4)	0.04179 (15)
Cl2	0.17398 (6)	0.08112 (5)	0.27101 (5)	0.0583 (2)
Hg1	0.063397 (7)	0.164790 (6)	0.357762 (6)	0.03372 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0263 (10)	0.0325 (12)	0.0237 (11)	0.0028 (9)	0.0011 (9)	−0.0008 (9)
C2	0.0365 (13)	0.0382 (14)	0.0305 (13)	−0.0066 (10)	−0.0014 (10)	−0.0039 (11)
C3	0.0328 (13)	0.0611 (19)	0.0336 (14)	−0.0083 (12)	−0.0045 (11)	−0.0068 (13)
C4	0.0345 (13)	0.072 (2)	0.0279 (13)	0.0039 (13)	−0.0069 (11)	0.0007 (13)
C5	0.0421 (14)	0.0491 (16)	0.0301 (13)	0.0088 (12)	0.0002 (11)	0.0075 (12)
C6	0.0299 (11)	0.0332 (12)	0.0236 (11)	0.0046 (9)	0.0023 (9)	0.0005 (9)
C7	0.0309 (11)	0.0238 (10)	0.0268 (11)	0.0003 (8)	0.0015 (9)	0.0001 (9)
C8	0.0380 (12)	0.0284 (12)	0.0331 (13)	−0.0074 (10)	−0.0037 (10)	−0.0004 (10)
C9	0.0421 (13)	0.0332 (12)	0.0311 (13)	0.0104 (11)	0.0032 (11)	−0.0015 (10)
C10	0.0309 (11)	0.0270 (11)	0.0238 (11)	0.0008 (9)	0.0030 (9)	−0.0001 (9)
C11	0.0265 (10)	0.0259 (11)	0.0216 (10)	−0.0032 (8)	0.0019 (8)	0.0019 (8)
C12	0.0374 (12)	0.0281 (11)	0.0309 (13)	0.0009 (10)	0.0024 (10)	−0.0010 (10)
C13	0.0382 (13)	0.0357 (13)	0.0426 (15)	0.0062 (11)	0.0017 (11)	0.0098 (11)
C14	0.0355 (13)	0.0461 (15)	0.0366 (15)	−0.0004 (12)	−0.0050 (11)	0.0117 (12)
C15	0.0407 (14)	0.0405 (14)	0.0274 (12)	−0.0082 (11)	−0.0055 (10)	0.0009 (10)
C16	0.0299 (11)	0.0272 (11)	0.0250 (11)	−0.0042 (9)	0.0020 (9)	0.0019 (9)
N1	0.0315 (9)	0.0242 (9)	0.0259 (10)	−0.0014 (7)	−0.0034 (8)	0.0016 (8)
N2	0.0299 (9)	0.0253 (9)	0.0252 (10)	−0.0001 (7)	0.0000 (8)	−0.0015 (8)
N3	0.0395 (11)	0.0247 (9)	0.0291 (10)	−0.0005 (8)	−0.0004 (8)	0.0045 (8)
N4	0.0426 (11)	0.0249 (9)	0.0254 (10)	−0.0004 (8)	0.0015 (9)	−0.0043 (8)
S1	0.0708 (5)	0.0221 (3)	0.0345 (3)	0.0013 (3)	−0.0047 (3)	−0.0040 (3)
Cl1	0.0454 (3)	0.0340 (3)	0.0460 (4)	−0.0095 (3)	0.0061 (3)	−0.0095 (3)
Cl2	0.0735 (5)	0.0413 (4)	0.0601 (5)	0.0137 (4)	0.0196 (4)	−0.0056 (3)
Hg1	0.04398 (6)	0.02599 (5)	0.03120 (5)	−0.00193 (4)	−0.00583 (4)	−0.00131 (4)

C1—C2	1.391 (3)	C9—H9B	0.97
C1—N1	1.395 (3)	C10—N2	1.324 (3)
C1—C6	1.400 (3)	C10—N4	1.350 (3)
C2—C3	1.380 (4)	C11—N2	1.391 (3)
C2—H2	0.93	C11—C12	1.392 (3)
C3—C4	1.393 (4)	C11—C16	1.397 (3)
C3—H3	0.93	C12—C13	1.380 (4)
C4—C5	1.378 (4)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.398 (4)
C5—C6	1.390 (4)	C13—H13	0.93
C5—H5	0.93	C14—C15	1.373 (4)
C6—N3	1.380 (3)	C14—H14	0.93
C7—N1	1.324 (3)	C15—C16	1.394 (3)
C7—N3	1.348 (3)	C15—H15	0.93
C7—C8	1.481 (3)	C16—N4	1.382 (3)
C8—S1	1.817 (3)	N1—Hg1	2.2991 (19)
C8—H8A	0.97	N2—Hg1	2.2471 (19)
C8—H8B	0.97	N3—H3N	0.86
C9—C10	1.487 (3)	N4—H4N	0.86
C9—S1	1.818 (3)	Cl1—Hg1	2.4554 (7)
C9—H9A	0.97	Cl2—Hg1	2.4459 (7)
C2—C1—N1	130.5 (2)	N2—C11—C16	108.38 (19)
C2—C1—C6	120.9 (2)	C12—C11—C16	120.7 (2)
N1—C1—C6	108.6 (2)	C13—C12—C11	116.8 (2)
C3—C2—C1	116.9 (3)	C13—C12—H12	121.6
C3—C2—H2	121.5	C11—C12—H12	121.6
C1—C2—H2	121.5	C12—C13—C14	122.1 (3)
C2—C3—C4	121.8 (3)	C12—C13—H13	118.9
C2—C3—H3	119.1	C14—C13—H13	118.9
C4—C3—H3	119.1	C15—C14—C13	121.6 (2)
C5—C4—C3	122.1 (3)	C15—C14—H14	119.2
C5—C4—H4	119	C13—C14—H14	119.2
C3—C4—H4	119	C14—C15—C16	116.5 (2)
C4—C5—C6	116.3 (3)	C14—C15—H15	121.7
C4—C5—H5	121.8	C16—C15—H15	121.7
C6—C5—H5	121.8	N4—C16—C15	132.4 (2)
N3—C6—C5	132.7 (2)	N4—C16—C11	105.41 (19)
N3—C6—C1	105.2 (2)	C15—C16—C11	122.2 (2)
C5—C6—C1	122.0 (2)	C7—N1—C1	106.27 (19)
N1—C7—N3	111.4 (2)	C7—N1—Hg1	132.12 (16)
N1—C7—C8	124.9 (2)	C1—N1—Hg1	121.26 (15)
N3—C7—C8	123.7 (2)	C10—N2—C11	106.81 (19)
C7—C8—S1	113.73 (18)	C10—N2—Hg1	128.73 (16)
C7—C8—H8A	108.8	C11—N2—Hg1	124.43 (14)
S1—C8—H8A	108.8	C7—N3—C6	108.5 (2)
C7—C8—H8B	108.8	C7—N3—H3N	125.8
S1—C8—H8B	108.8	C6—N3—H3N	125.8
H8A—C8—H8B	107.7	C10—N4—C16	108.43 (19)
C10—C9—S1	113.62 (19)	C10—N4—H4N	125.8
C10—C9—H9A	108.8	C16—N4—H4N	125.8
S1—C9—H9A	108.8	C8—S1—C9	101.89 (12)
C10—C9—H9B	108.8	N2—Hg1—N1	104.46 (7)
S1—C9—H9B	108.8	N2—Hg1—Cl2	119.40 (5)
H9A—C9—H9B	107.7	N1—Hg1—Cl2	101.48 (5)
N2—C10—N4	111.0 (2)	N2—Hg1—Cl1	111.85 (5)
N2—C10—C9	124.9 (2)	N1—Hg1—Cl1	107.47 (5)
N4—C10—C9	124.1 (2)	Cl2—Hg1—Cl1	110.77 (3)
N2—C11—C12	130.9 (2)
N1—C1—C2—C3	−179.5 (2)	C2—C1—N1—Hg1	5.2 (3)
C6—C1—C2—C3	0.3 (4)	C6—C1—N1—Hg1	−174.53 (15)
C1—C2—C3—C4	0.6 (4)	N4—C10—N2—C11	1.2 (3)
C2—C3—C4—C5	−0.9 (5)	C9—C10—N2—C11	−178.4 (2)
C3—C4—C5—C6	0.3 (4)	N4—C10—N2—Hg1	−176.69 (15)
C4—C5—C6—N3	179.2 (3)	C9—C10—N2—Hg1	3.7 (3)
C4—C5—C6—C1	0.5 (4)	C12—C11—N2—C10	178.5 (2)
C2—C1—C6—N3	−179.8 (2)	C16—C11—N2—C10	−1.2 (2)
N1—C1—C6—N3	0.0 (3)	C12—C11—N2—Hg1	−3.4 (3)
C2—C1—C6—C5	−0.8 (4)	C16—C11—N2—Hg1	176.80 (14)
N1—C1—C6—C5	178.9 (2)	N1—C7—N3—C6	−0.9 (3)
N1—C7—C8—S1	−91.1 (3)	C8—C7—N3—C6	179.1 (2)
N3—C7—C8—S1	88.9 (3)	C5—C6—N3—C7	−178.3 (3)
S1—C9—C10—N2	−102.2 (3)	C1—C6—N3—C7	0.6 (3)
S1—C9—C10—N4	78.2 (3)	N2—C10—N4—C16	−0.8 (3)
N2—C11—C12—C13	179.7 (2)	C9—C10—N4—C16	178.9 (2)
C16—C11—C12—C13	−0.6 (3)	C15—C16—N4—C10	179.2 (3)
C11—C12—C13—C14	−0.3 (4)	C11—C16—N4—C10	0.0 (3)
C12—C13—C14—C15	0.3 (4)	C7—C8—S1—C9	67.4 (2)
C13—C14—C15—C16	0.7 (4)	C10—C9—S1—C8	67.0 (2)
C14—C15—C16—N4	179.2 (2)	C10—N2—Hg1—N1	26.7 (2)
C14—C15—C16—C11	−1.6 (4)	C11—N2—Hg1—N1	−150.88 (17)
N2—C11—C16—N4	0.8 (2)	C10—N2—Hg1—Cl2	139.14 (18)
C12—C11—C16—N4	−179.0 (2)	C11—N2—Hg1—Cl2	−38.46 (19)
N2—C11—C16—C15	−178.6 (2)	C10—N2—Hg1—Cl1	−89.2 (2)
C12—C11—C16—C15	1.6 (3)	C11—N2—Hg1—Cl1	93.18 (17)
N3—C7—N1—C1	0.9 (3)	C7—N1—Hg1—N2	29.2 (2)
C8—C7—N1—C1	−179.1 (2)	C1—N1—Hg1—N2	−158.52 (16)
N3—C7—N1—Hg1	173.99 (16)	C7—N1—Hg1—Cl2	−95.5 (2)
C8—C7—N1—Hg1	−6.0 (4)	C1—N1—Hg1—Cl2	76.74 (17)
C2—C1—N1—C7	179.2 (3)	C7—N1—Hg1—Cl1	148.2 (2)
C6—C1—N1—C7	−0.5 (3)	C1—N1—Hg1—Cl1	−39.57 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl1i	0.86	2.35	3.178 (2)	163
N4—H4N···Cl2ii	0.86	2.76	3.508 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯Cl1i	0.86	2.35	3.178 (2)	163
N4—H4N⋯Cl2ii	0.86	2.76	3.508 (2)	147

Symmetry codes: (i) ; (ii) .