(2-{[4-(Chlorido­mercur­yl)phen­yl]imino­meth­yl}pyridine-κ2N,N′)di­iodido­mercury(II) dimethyl sulfoxide monosolvate

Basu Baul, T.S.; Longkumer, I.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813029693

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m633-m634

doi:10.1107/S1600536813029693

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(2-{[4-(Chloridomercuryl)phenyl]iminomethyl}pyridine-κ²N,N′)diiodidomercury(II) dimethyl sulfoxide monosolvate

Tushar S. Basu Baul,^a ‡ Imliwati Longkumer,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong 793 022, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 October 2013; accepted 28 October 2013; online 6 November 2013)

The title dimethyl sulfoxide solvate, [Hg₂(C₁₂H₉ClN₂)I₂]·C₂H₆OS, features tetrahedrally 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 interactions are apparent in the crystal packing with the tetrahedrally 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] interactions, respectively. Mercury-containing molecules stack along the a axis, are connected by π–π interactions [inter-centroid distance between pyridine and benzene rings = 3.772 (7) Å] and define channels in which the dimethyl sulfoxide molecules reside. The latter are connected by the aforementioned Hg⋯O interactions as well as C—H⋯I and C—H⋯O interactions, resulting in a three-dimensional architecture.

CCDC reference: 969086

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_r = 949.77
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.143
S = 1.03
4848 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 4.40 e Å⁻³
Δρ_min = −1.45 e Å⁻³

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) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+2, -y+1, -z+1.

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 ).

Supporting information

CCDC reference: 969086

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536813029693/hg5358sup1.cif

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

checkCIF report

Comment top

Investigations in into the coordination chemistry of divalent zinc triad elements with (E)-N-(pyridin-2-ylmethylidene)arylamine ligands (Basu Baul, Kundu, Höpfl et al., 2013; Basu Baul, Kundu, Linden et al., 2013; Basu Baul, Kundu, Mitra et al. 2013) led to the isolation of the title compound, (I).

In (I), Fig. 1, the 2-[((4-chloromercuryl)phenyl)iminomethyl]pyridine, an organomercury ligand, chelates the Hg1 atom with the Hg1—N1(pyridyl) bond length being shorter than the Hg—N2(imino) bond in accord with related structures (Basu Baul, Kundu, Höpfl et al., 2013). The five-membered chelate ring is an envelope with the Hg1 atom lying 0.24 (2) Å out of the plane of the remaining four atoms (r.m.s. deviation = 0.0022 Å). In terms of angles, the major distortions from the ideal tetrahedral geometry about the Hg1 atom is found in the acute chelate angle (69.6 (3)°) and the wide angle subtended by the large I atoms (142.80 (4)°). The benzene ring carrying the HgCl atoms is almost co-planar to the pyridyl ring, forming a dihedral angle of 6.5 (6)°. The geometry about the Hg2 atom is linear as expected (177.0 (4)°).

In the crystal packing, centrosymmetrically related molecules associate via weak Hg···I secondary interactions: Hg1···I1ⁱ = 3.7027 (12) Å for symmetry operation i: -x, 1 - y, -z. These assemble into columns along the a axis via weak π—π interactions formed between the pyridyl and benzene rings [inter-centroid distance = 3.772 (7) Å for symmetry operation -1 + x, y, z]. In this way channels are formed in which reside the dimethyl sulfoxide molecules of solvation which are connected by weak Hg2···O1 secondary interactions [2.921 (12) Å] as well as weak C—H···I, O contacts, Fig. 2 and Table 2.

Related literature top

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 top

To a hot solution of 2-[((4-chloromercuryl)phenyl)iminomethyl]pyridine (0.50 g, 1.19 mmol) in methanol (70 ml) was added a solution of HgI₂ (0.54 g, 1.18 mmol) in methanol (10 ml) under stirring conditions, whereupon a yellow precipitate formed immediately. The mixture was stirred at ambient temperature for 4 h. The precipitate was filtered, washed with hot methanol (3 x 5 ml) and dried in vacuo. The yellow product (0.79 g, M. pt. 495–497 K (dec.)) so obtained was insoluble in common organic solvents. The yellow crystals of compound suitable for an X-ray crystal-structure determination were obtained from dimethyl sulfoxide by slow evaporation of the solvent at room temperature. M. pt. 447–449 K. CH&N elemental analysis, calculated for C₁₄H₁₅ClHg₂I₂N₂OS: C, 17.69, H, 1.59, N, 2.95%; Found: C, 17.82; H, 1.65; N, 3.07%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); 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).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the unit-cell contents in projection down the a axis in (I). The Hg···I, O secondary interactions are shown as pink and black dashed lines, respectively. The π—π, C—H···I and C—H···O interactions are shown as purple, green and orange dashed lines, respectively.

(2-{[4-(Chloridomercuryl)phenyl]iminomethyl}pyridine-κ²N,N')diiodidomercury(II) dimethyl sulfoxide monosolvate top

Crystal data top

[Hg₂(C₁₂H₉ClN₂)I₂]·C₂H₆OS	Z = 2
M_r = 949.77	F(000) = 840
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.038
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→11
T_min = 0.358, T_max = 1.000	l = −17→17
12862 measured reflections

Refinement top

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(F_o²) + (0.0612P)² + 7.0509P] where P = (F_o² + 2F_c²)/3
4848 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 4.40 e Å⁻³
0 restraints	Δρ_min = −1.45 e Å⁻³

Crystal data top

[Hg₂(C₁₂H₉ClN₂)I₂]·C₂H₆OS	γ = 79.362 (6)°
M_r = 949.77	V = 1050.74 (12) Å³
Triclinic, P1	Z = 2
a = 8.5795 (6) Å	Mo Kα radiation
b = 9.8373 (7) Å	µ = 17.76 mm⁻¹
c = 13.6999 (8) Å	T = 295 K
α = 70.030 (6)°	0.20 × 0.10 × 0.04 mm
β = 76.779 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4848 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	3470 reflections with I > 2σ(I)
T_min = 0.358, T_max = 1.000	R_int = 0.038
12862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.03	Δρ_max = 4.40 e Å⁻³
4848 reflections	Δρ_min = −1.45 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: basubaul@hotmail.com.

Acknowledgements

The financial support of the University Grants Commission, New Delhi, India (F. No. 42–396/2013 (SR) TSBB), is gratefully acknowledged. The authors also thank the Ministry of Higher Education (Malaysia) and the University of Malaya for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

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