(2-{[4-(Chlorido-mercur-yl)phen-yl]imino-meth-yl}pyridine-κ(2) N,N')di-iodido-mercury(II) dimethyl sulfoxide monosolvate.

The title dimethyl sulfoxide solvate, [Hg2(C12H9ClN2)I2]·C2H6OS, features tetra-hedrally and linearly coordinated Hg(II) atoms. The distorted tetrahedral coordination sphere is defined by chelating N atoms that define an acute angle [69.6 (3)°] and two I atoms that form a wide angle [142.80 (4)°]. The linearly coordinated Hg(II) atom [177.0 (4)°] exists with a donor set defined by C and Cl atoms. Secondary inter-actions are apparent in the crystal packing with the tetra-hedrally and linearly coordinated Hg(II) atoms expanding their coordination environments by forming weak Hg⋯I [3.772 (7) Å] and Hg⋯O [2.921 (12) Å] inter-actions, respectively. Mercury-containing mol-ecules stack along the a axis, are connected by π-π inter-actions [inter-centroid distance between pyridine and benzene rings = 3.772 (7) Å] and define channels in which the dimethyl sulfoxide mol-ecules reside. The latter are connected by the aforementioned Hg⋯O inter-actions as well as C-H⋯I and C-H⋯O inter-actions, resulting in a three-dimensional architecture.

Related literature

For background to the structural, spectroscopic and biological properties of zinc triad elements with (E)-N-(pyridin-2-yl­methyl­idene)aryl­amine-type ligands, see: Basu Baul, Kundu, Höpfl et al. (2013 ▶); Basu Baul, Kundu, Linden et al. (2013 ▶); Basu Baul, Kundu, Mitra et al. (2013 ▶).

Experimental

Crystal data

[Hg2(C12H9ClN2)I2]·C2H6OS

M = 949.77

Triclinic,

a = 8.5795 (6) Å

b = 9.8373 (7) Å

c = 13.6999 (8) Å

α = 70.030 (6)°

β = 76.779 (5)°

γ = 79.362 (6)°

V = 1050.74 (12) Å3

Z = 2

Mo Kα radiation

μ = 17.76 mm−1

T = 295 K

0.20 × 0.10 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.358, T max = 1.000

12862 measured reflections

4848 independent reflections

3470 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.143

S = 1.03

4848 reflections

208 parameters

H-atom parameters constrained

Δρmax = 4.40 e Å−3

Δρmin = −1.45 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536813029693/hg5358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029693/hg5358Isup2.hkl

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

[Hg2(C12H9ClN2)I2]·C2H6OS	Z = 2
Mr = 949.77	F(000) = 840
Triclinic, P1	Dx = 3.002 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5795 (6) Å	Cell parameters from 3179 reflections
b = 9.8373 (7) Å	θ = 2.9–27.5°
c = 13.6999 (8) Å	µ = 17.76 mm−1
α = 70.030 (6)°	T = 295 K
β = 76.779 (5)°	Prism, yellow
γ = 79.362 (6)°	0.20 × 0.10 × 0.04 mm
V = 1050.74 (12) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4848 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3470 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→11
Tmin = 0.358, Tmax = 1.000	l = −17→17
12862 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0612P)2 + 7.0509P] where P = (Fo2 + 2Fc2)/3
4848 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 4.40 e Å−3
0 restraints	Δρmin = −1.45 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
Hg1	0.20510 (6)	0.31203 (6)	0.05498 (4)	0.05488 (18)
Hg2	0.86627 (6)	0.16239 (6)	0.39910 (4)	0.05315 (17)
I1	0.45868 (12)	0.28767 (13)	−0.09397 (7)	0.0740 (3)
I2	0.03457 (13)	0.49555 (11)	0.15600 (8)	0.0681 (3)
Cl1	1.0870 (4)	0.1770 (4)	0.4659 (3)	0.0679 (10)
S1	0.7709 (5)	0.4377 (4)	0.5467 (3)	0.0681 (10)
O1	0.6835 (13)	0.3252 (12)	0.5397 (10)	0.083 (3)
N1	0.0365 (11)	0.1207 (10)	0.1108 (6)	0.040 (2)
N2	0.2980 (10)	0.1073 (11)	0.2044 (7)	0.041 (2)
C1	−0.0913 (14)	0.1244 (14)	0.0724 (9)	0.047 (3)
H1	−0.1221	0.2088	0.0207	0.057*
C2	−0.1844 (13)	0.0080 (15)	0.1050 (9)	0.046 (3)
H2	−0.2765	0.0153	0.0777	0.056*
C3	−0.1338 (15)	−0.1155 (16)	0.1780 (10)	0.054 (3)
H3	−0.1900	−0.1963	0.2004	0.065*
C4	−0.0009 (14)	−0.1216 (14)	0.2188 (10)	0.052 (3)
H4	0.0327	−0.2057	0.2698	0.063*
C5	0.0836 (12)	−0.0018 (12)	0.1837 (7)	0.036 (2)
C6	0.2212 (13)	−0.0050 (14)	0.2305 (9)	0.046 (3)
H6	0.2548	−0.0902	0.2806	0.056*
C7	0.4272 (13)	0.1129 (13)	0.2514 (8)	0.039 (2)
C8	0.4834 (14)	−0.0020 (15)	0.3326 (9)	0.048 (3)
H8	0.4374	−0.0889	0.3593	0.058*
C9	0.6106 (14)	0.0163 (16)	0.3731 (9)	0.054 (3)
H9	0.6495	−0.0600	0.4272	0.065*
C10	0.6798 (13)	0.1435 (14)	0.3355 (9)	0.043 (3)
C11	0.6269 (15)	0.2541 (14)	0.2524 (10)	0.050 (3)
H11	0.6760	0.3393	0.2234	0.060*
C12	0.4978 (16)	0.2369 (13)	0.2117 (10)	0.050 (3)
H12	0.4605	0.3124	0.1565	0.060*
C13	0.632 (2)	0.541 (2)	0.6187 (12)	0.092 (6)
H13A	0.6148	0.4852	0.6922	0.138*
H13B	0.5322	0.5648	0.5934	0.138*
H13C	0.6752	0.6289	0.6096	0.138*
C14	0.774 (2)	0.570 (2)	0.4243 (12)	0.093 (6)
H14A	0.8405	0.5315	0.3709	0.140*
H14B	0.8175	0.6531	0.4245	0.140*
H14C	0.6665	0.5984	0.4098	0.140*

	U11	U22	U33	U12	U13	U23
Hg1	0.0592 (3)	0.0483 (3)	0.0548 (3)	−0.0123 (2)	−0.0089 (2)	−0.0109 (2)
Hg2	0.0496 (3)	0.0575 (4)	0.0632 (3)	−0.0044 (2)	−0.0222 (2)	−0.0257 (2)
I1	0.0623 (6)	0.0922 (8)	0.0572 (5)	−0.0182 (5)	0.0016 (4)	−0.0137 (5)
I2	0.0842 (7)	0.0544 (6)	0.0677 (6)	0.0013 (5)	−0.0185 (5)	−0.0232 (4)
Cl1	0.062 (2)	0.064 (2)	0.090 (2)	−0.0103 (17)	−0.0408 (18)	−0.0204 (19)
S1	0.068 (2)	0.056 (2)	0.084 (2)	−0.0134 (18)	−0.0129 (18)	−0.0236 (19)
O1	0.079 (7)	0.053 (7)	0.118 (9)	−0.012 (6)	−0.014 (6)	−0.030 (6)
N1	0.043 (5)	0.039 (6)	0.036 (4)	−0.007 (4)	−0.008 (4)	−0.008 (4)
N2	0.033 (5)	0.040 (6)	0.047 (5)	−0.006 (4)	−0.006 (4)	−0.010 (4)
C1	0.043 (6)	0.044 (7)	0.051 (6)	−0.005 (5)	−0.005 (5)	−0.012 (5)
C2	0.037 (6)	0.061 (8)	0.058 (7)	−0.001 (5)	−0.003 (5)	−0.046 (6)
C3	0.048 (7)	0.054 (8)	0.066 (8)	−0.024 (6)	−0.005 (6)	−0.019 (6)
C4	0.050 (7)	0.042 (7)	0.064 (8)	−0.010 (6)	−0.013 (6)	−0.012 (6)
C5	0.041 (6)	0.040 (6)	0.033 (5)	−0.014 (5)	−0.001 (4)	−0.016 (4)
C6	0.046 (6)	0.045 (7)	0.047 (6)	−0.013 (5)	−0.012 (5)	−0.008 (5)
C7	0.040 (6)	0.036 (6)	0.044 (6)	−0.005 (5)	−0.004 (4)	−0.018 (5)
C8	0.048 (7)	0.054 (8)	0.044 (6)	−0.015 (6)	−0.008 (5)	−0.013 (5)
C9	0.046 (7)	0.066 (9)	0.048 (6)	0.003 (6)	−0.017 (5)	−0.015 (6)
C10	0.042 (6)	0.047 (7)	0.050 (6)	−0.004 (5)	−0.014 (5)	−0.025 (5)
C11	0.052 (7)	0.036 (7)	0.065 (7)	−0.008 (5)	−0.016 (6)	−0.016 (6)
C12	0.070 (8)	0.027 (6)	0.059 (7)	−0.008 (6)	−0.031 (6)	−0.007 (5)
C13	0.119 (15)	0.087 (14)	0.063 (9)	−0.042 (11)	0.027 (9)	−0.028 (9)
C14	0.131 (15)	0.085 (13)	0.071 (10)	−0.061 (12)	0.014 (9)	−0.029 (9)

Hg1—I1	2.6581 (11)	C4—H4	0.9300
Hg1—I2	2.6684 (12)	C5—C6	1.458 (14)
Hg1—N1	2.395 (9)	C6—H6	0.9300
Hg1—N2	2.493 (9)	C7—C12	1.350 (16)
Hg2—Cl1	2.330 (3)	C7—C8	1.391 (16)
Hg2—C10	2.052 (10)	C8—C9	1.396 (16)
S1—O1	1.485 (11)	C8—H8	0.9300
S1—C14	1.734 (16)	C9—C10	1.370 (18)
S1—C13	1.766 (19)	C9—H9	0.9300
N1—C1	1.310 (14)	C10—C11	1.375 (16)
N1—C5	1.340 (13)	C11—C12	1.408 (16)
N2—C6	1.293 (14)	C11—H11	0.9300
N2—C7	1.421 (13)	C12—H12	0.9300
C1—C2	1.405 (17)	C13—H13A	0.9600
C1—H1	0.9300	C13—H13B	0.9600
C2—C3	1.356 (18)	C13—H13C	0.9600
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.363 (16)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.384 (15)
N1—Hg1—N2	69.6 (3)	N2—C6—H6	119.1
N1—Hg1—I1	114.5 (2)	C5—C6—H6	119.1
N2—Hg1—I1	98.0 (2)	C12—C7—C8	120.1 (10)
N1—Hg1—I2	102.0 (2)	C12—C7—N2	116.4 (10)
N2—Hg1—I2	101.1 (2)	C8—C7—N2	123.4 (10)
I1—Hg1—I2	142.80 (4)	C7—C8—C9	118.4 (11)
C10—Hg2—Cl1	177.0 (4)	C7—C8—H8	120.8
O1—S1—C14	103.7 (8)	C9—C8—H8	120.8
O1—S1—C13	107.2 (8)	C10—C9—C8	121.9 (11)
C14—S1—C13	96.1 (9)	C10—C9—H9	119.1
C1—N1—C5	118.4 (9)	C8—C9—H9	119.1
C1—N1—Hg1	125.4 (7)	C11—C10—C9	119.0 (10)
C5—N1—Hg1	116.1 (6)	C11—C10—Hg2	121.3 (9)
C6—N2—C7	124.2 (9)	C9—C10—Hg2	119.7 (8)
C6—N2—Hg1	112.9 (7)	C10—C11—C12	119.4 (11)
C7—N2—Hg1	122.8 (7)	C10—C11—H11	120.3
N1—C1—C2	123.7 (11)	C12—C11—H11	120.3
N1—C1—H1	118.1	C7—C12—C11	121.2 (11)
C2—C1—H1	118.1	C7—C12—H12	119.4
C3—C2—C1	117.0 (11)	C11—C12—H12	119.4
C3—C2—H2	121.5	S1—C13—H13A	109.5
C1—C2—H2	121.5	S1—C13—H13B	109.5
C4—C3—C2	120.2 (11)	H13A—C13—H13B	109.5
C4—C3—H3	119.9	S1—C13—H13C	109.5
C2—C3—H3	119.9	H13A—C13—H13C	109.5
C3—C4—C5	119.6 (11)	H13B—C13—H13C	109.5
C3—C4—H4	120.2	S1—C14—H14A	109.5
C5—C4—H4	120.2	S1—C14—H14B	109.5
N1—C5—C4	121.1 (10)	H14A—C14—H14B	109.5
N1—C5—C6	118.9 (9)	S1—C14—H14C	109.5
C4—C5—C6	119.9 (10)	H14A—C14—H14C	109.5
N2—C6—C5	121.9 (10)	H14B—C14—H14C	109.5
N2—Hg1—N1—C1	177.0 (10)	C1—N1—C5—C6	−177.2 (11)
I1—Hg1—N1—C1	−93.4 (10)	Hg1—N1—C5—C6	5.9 (13)
I2—Hg1—N1—C1	79.5 (10)	C3—C4—C5—N1	0.5 (19)
N2—Hg1—N1—C5	−6.4 (7)	C3—C4—C5—C6	177.1 (12)
I1—Hg1—N1—C5	83.2 (8)	C7—N2—C6—C5	176.5 (10)
I2—Hg1—N1—C5	−103.9 (8)	Hg1—N2—C6—C5	−6.5 (15)
N1—Hg1—N2—C6	6.6 (8)	N1—C5—C6—N2	0.7 (18)
I1—Hg1—N2—C6	−106.7 (8)	C4—C5—C6—N2	−176.0 (12)
I2—Hg1—N2—C6	105.4 (8)	C6—N2—C7—C12	177.5 (12)
N1—Hg1—N2—C7	−176.3 (9)	Hg1—N2—C7—C12	0.8 (15)
I1—Hg1—N2—C7	70.4 (8)	C6—N2—C7—C8	−1.3 (18)
I2—Hg1—N2—C7	−77.5 (8)	Hg1—N2—C7—C8	−178.0 (9)
C5—N1—C1—C2	1.4 (18)	C12—C7—C8—C9	1.7 (19)
Hg1—N1—C1—C2	177.9 (9)	N2—C7—C8—C9	−179.6 (11)
N1—C1—C2—C3	−2.0 (19)	C8—C9—C10—Hg2	180.0 (10)
C1—C2—C3—C4	1.8 (19)	Hg2—C10—C11—C12	−179.5 (10)
C1—N1—C5—C4	−0.6 (17)	N2—C7—C12—C11	−180.0 (12)
Hg1—N1—C5—C4	−177.4 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.54	3.458 (18)	171
C9—H9···Cl1ii	0.93	2.83	3.625 (13)	145
C13—H13C···Cl1iii	0.96	2.83	3.721 (19)	155

Table 1

Selected bond lengths (Å)

Hg1—I1	2.6581 (11)
Hg1—I2	2.6684 (12)
Hg1—N1	2.395 (9)
Hg1—N2	2.493 (9)
Hg2—Cl1	2.330 (3)
Hg2—C10	2.052 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.54	3.458 (18)	171
C9—H9⋯Cl1ii	0.93	2.83	3.625 (13)	145
C13—H13C⋯Cl1iii	0.96	2.83	3.721 (19)	155

Symmetry codes: (i) ; (ii) ; (iii) .