Bis((E)-2-{3-[4-(1H-imidazol-1-yl-κN3)styr­yl]-5,5-di­methyl­cyclo­hex-2-enyl­idene}malono­nitrile)­diiodido­mercury(II)

Xi, W.-G.; Wu, Z.-C.; Zhou, H.-P.

doi:10.1107/S1600536813025191

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page m548

doi:10.1107/S1600536813025191

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Bis((E)-2-{3-[4-(1H-imidazol-1-yl-κN³)styryl]-5,5-dimethylcyclohex-2-enylidene}malononitrile)diiodidomercury(II)

Wen-Gang Xi,^a,^b Zhi-Chao Wu ^a,^b and Hong-Ping Zhou ^a,^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 21 July 2013; accepted 11 September 2013; online 21 September 2013)

In the title compound, [HgI₂(C₂₂H₂₀N₄)₂], the Hg^II cation is situated on a twofold rotation axis and is coordinated by two iodide anions and two imidazolyl N atoms in a distorted tetrahedral geometry. In the crystal, C—H⋯I interactions link the molecules into chains extending in [010], which are further linked into sheets parallel to (100) through C—H⋯N hydrogen bonding interactions.

CCDC reference: 957793

Related literature

For the crystal structure of the organic ligand of the title compound, see: Zheng et al. (2013 ). For mercury(II) complexes in which the Hg(II) cation is four-coordinated by two terminal iodide ions and two N atoms from organic ligands in a distorted tetrahedral geometry, see: Li (2011 ); Shirvan et al. (2012 ).

Experimental

Crystal data

[HgI₂(C₂₂H₂₀N₄)₂]
M_r = 1135.23
Monoclinic, P 2/c
a = 18.768 (3) Å
b = 6.4890 (9) Å
c = 18.681 (3) Å
β = 103.896 (10)°
V = 2208.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 4.92 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.320, T_max = 0.439
14665 measured reflections
3889 independent reflections
3647 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.092
S = 1.04
3889 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 2.28 e Å⁻³
Δρ_min = −1.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2ⁱ	0.93	2.70	3.541 (15)	151
C18—H18⋯I1ⁱⁱ	0.93	3.09	3.864 (5)	142
Symmetry codes: (i) $[x, -y+3, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 957793

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536813025191/cq2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025191/cq2006Isup2.hkl

checkCIF report

Comment top

The organic ligand of the title compound has previously been investigated for its optical properties (Zheng et al., 2013). In addition, some mercury(II) complexes in which the Hg(II) cation is four-coordinated by two terminal iodide ions and two nitrogen atoms from organic ligands to form distorted tetrahedral geometry have been reported (Li, 2011; Shirvan et al., 2012). In this study, we report the crystal structure of the title compound (Fig. 1). In the molecular packing structure of the compound, intermolecular C—H···I interactions link the molecules into chains. The neighboring chains are further linked into sheets through C—H···N hydrogen bonding interactions (Fig.2). Intermolecular hydrogen bonds lengths and angles are reported in Table.1.

Related literature top

For the crystal structure of the organic ligand of the title compound, see: Zheng et al. (2013). For mercury(II) complexes in which the Hg(II) cation is four-coordinated by two terminal iodide ions and two N atoms from organic ligands in a distorted tetrahedral geometry, see: Li (2011); Shirvan et al. (2012).

Experimental top

For the preparation of the title compound, a solution of HgI₂ (0.1 g, 0.22 mmol) in methanol (10 mL) was carefully layered on top of the surface of the solution of (E)-2-(3-(4-(1H-imidazol-1-yl)styryl)-5,5-dimethylcyclohex-2- enylidene) malononitrile (0.15 g, 0.44 mmol) in chloroform (10 mL). Crystals were obtained after a week at about 298 K (yield 0.16 g, 64.0%).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of the title molecule. [Symmetry code: #1: -x + 1,y,-z + 3/2].
	Fig. 2. : Packing diagram of the title compound viewed along b axis. Intermolecular C—H···I and C—H···N interactions are shown as dashed lines in pink and yellow, respectively.

Bis((E)-2-{3-[4-(1H-imidazol-1-yl-κN³)styryl]-5,5-dimethylcyclohex-2-enylidene}malononitrile)diiodidomercury(II) top

Crystal data top

[HgI₂(C₂₂H₂₀N₄)₂]	Z = 2
M_r = 1135.23	F(000) = 1092
Monoclinic, P2/c	D_x = 1.707 Mg m⁻³
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71069 Å
a = 18.768 (3) Å	µ = 4.92 mm⁻¹
b = 6.4890 (9) Å	T = 298 K
c = 18.681 (3) Å	Block, red
β = 103.896 (10)°	0.30 × 0.20 × 0.20 mm
V = 2208.5 (5) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3889 independent reflections
Radiation source: fine-focus sealed tube	3647 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→22
T_min = 0.320, T_max = 0.439	k = −7→7
14665 measured reflections	l = −22→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0496P)² + 4.7641P] where P = (F_o² + 2F_c²)/3
3889 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 2.28 e Å⁻³
0 restraints	Δρ_min = −1.86 e Å⁻³

Crystal data top

[HgI₂(C₂₂H₂₀N₄)₂]	V = 2208.5 (5) Å³
M_r = 1135.23	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 18.768 (3) Å	µ = 4.92 mm⁻¹
b = 6.4890 (9) Å	T = 298 K
c = 18.681 (3) Å	0.30 × 0.20 × 0.20 mm
β = 103.896 (10)°

Data collection top

Bruker SMART APEX CCD diffractometer	3889 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3647 reflections with I > 2σ(I)
T_min = 0.320, T_max = 0.439	R_int = 0.042
14665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.04	Δρ_max = 2.28 e Å⁻³
3889 reflections	Δρ_min = −1.86 e Å⁻³
251 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	0.5000	−0.05717 (4)	0.7500	0.04225 (11)
I1	0.40548 (2)	−0.27343 (6)	0.811929 (18)	0.05948 (14)
N1	0.0943 (6)	2.1499 (14)	0.1997 (5)	0.136 (4)
N2	0.2337 (6)	1.6553 (14)	0.1582 (5)	0.125 (3)
N3	0.4072 (2)	0.4228 (6)	0.5797 (2)	0.0361 (8)
N4	0.4591 (2)	0.1711 (6)	0.6528 (2)	0.0393 (9)
C1	0.2004 (5)	1.7214 (12)	0.1961 (4)	0.083 (2)
C2	0.1228 (5)	1.9987 (13)	0.2193 (5)	0.081 (2)
C3	0.1591 (3)	1.8091 (9)	0.2440 (4)	0.0589 (15)
C4	0.1556 (3)	1.7198 (8)	0.3090 (3)	0.0465 (12)
C5	0.1146 (3)	1.8174 (9)	0.3589 (3)	0.0541 (13)
H5A	0.0727	1.8906	0.3293	0.065*
H5B	0.1461	1.9179	0.3896	0.065*
C6	0.0875 (3)	1.6647 (9)	0.4086 (3)	0.0521 (13)
C7	0.0272 (4)	1.5276 (13)	0.3621 (4)	0.0748 (19)
H7A	0.0469	1.4494	0.3277	0.112*
H7B	−0.0124	1.6123	0.3356	0.112*
H7C	0.0092	1.4352	0.3939	0.112*
C8	0.0573 (5)	1.7859 (13)	0.4649 (4)	0.088 (2)
H8A	0.0171	1.8704	0.4396	0.132*
H8B	0.0953	1.8718	0.4935	0.132*
H8C	0.0406	1.6918	0.4969	0.132*
C9	0.1524 (3)	1.5320 (8)	0.4483 (3)	0.0501 (13)
H9A	0.1849	1.6155	0.4853	0.060*
H9B	0.1341	1.4208	0.4736	0.060*
C10	0.1955 (3)	1.4417 (7)	0.3981 (3)	0.0419 (11)
C11	0.1948 (3)	1.5315 (8)	0.3326 (3)	0.0474 (12)
H11	0.2206	1.4693	0.3017	0.057*
C12	0.2392 (3)	1.2574 (8)	0.4195 (3)	0.0471 (12)
H12	0.2619	1.2009	0.3849	0.057*
C13	0.2497 (3)	1.1623 (8)	0.4841 (3)	0.0454 (11)
H13	0.2279	1.2220	0.5188	0.055*
C14	0.2919 (3)	0.9732 (7)	0.5066 (3)	0.0421 (11)
C15	0.3278 (3)	0.8633 (8)	0.4615 (3)	0.0487 (12)
H15	0.3264	0.9124	0.4145	0.058*
C16	0.3653 (3)	0.6840 (8)	0.4851 (3)	0.0461 (12)
H16	0.3890	0.6139	0.4540	0.055*
C17	0.3677 (3)	0.6079 (7)	0.5546 (2)	0.0366 (10)
C18	0.3317 (3)	0.7111 (8)	0.6003 (3)	0.0469 (12)
H18	0.3324	0.6597	0.6470	0.056*
C19	0.2945 (3)	0.8915 (8)	0.5759 (3)	0.0485 (12)
H19	0.2705	0.9605	0.6069	0.058*
C20	0.4439 (3)	0.3009 (9)	0.5405 (3)	0.0488 (12)
H20	0.4467	0.3207	0.4920	0.059*
C21	0.4750 (3)	0.1469 (8)	0.5857 (3)	0.0476 (12)
H21	0.5030	0.0407	0.5732	0.057*
C22	0.4183 (3)	0.3371 (7)	0.6475 (3)	0.0413 (11)
H22	0.3995	0.3893	0.6856	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0579 (2)	0.04093 (17)	0.03286 (16)	0.000	0.02053 (12)	0.000
I1	0.0757 (3)	0.0706 (3)	0.0394 (2)	−0.0295 (2)	0.02794 (18)	−0.01058 (15)
N1	0.165 (8)	0.101 (6)	0.144 (8)	0.062 (6)	0.038 (6)	0.065 (6)
N2	0.177 (8)	0.111 (6)	0.123 (6)	0.046 (6)	0.104 (7)	0.048 (5)
N3	0.040 (2)	0.037 (2)	0.0310 (19)	−0.0014 (16)	0.0078 (16)	0.0001 (15)
N4	0.054 (2)	0.035 (2)	0.0290 (18)	0.0050 (18)	0.0109 (17)	0.0047 (15)
C1	0.102 (6)	0.079 (5)	0.079 (5)	0.022 (4)	0.046 (5)	0.039 (4)
C2	0.094 (6)	0.073 (4)	0.078 (5)	0.021 (4)	0.021 (4)	0.030 (4)
C3	0.056 (3)	0.055 (3)	0.068 (4)	0.009 (3)	0.018 (3)	0.021 (3)
C4	0.039 (3)	0.044 (3)	0.054 (3)	0.001 (2)	0.008 (2)	0.008 (2)
C5	0.058 (3)	0.042 (3)	0.062 (3)	0.009 (2)	0.014 (3)	0.004 (2)
C6	0.049 (3)	0.055 (3)	0.054 (3)	0.005 (3)	0.017 (2)	−0.001 (3)
C7	0.048 (4)	0.090 (5)	0.085 (5)	−0.011 (3)	0.014 (3)	0.004 (4)
C8	0.105 (6)	0.091 (5)	0.081 (5)	0.036 (5)	0.047 (5)	0.005 (4)
C9	0.058 (3)	0.045 (3)	0.047 (3)	−0.001 (2)	0.013 (3)	0.001 (2)
C10	0.038 (3)	0.037 (3)	0.048 (3)	−0.0038 (19)	0.006 (2)	0.002 (2)
C11	0.049 (3)	0.043 (3)	0.053 (3)	0.003 (2)	0.018 (2)	0.008 (2)
C12	0.050 (3)	0.041 (3)	0.053 (3)	0.001 (2)	0.018 (2)	0.005 (2)
C13	0.050 (3)	0.040 (3)	0.046 (3)	0.000 (2)	0.010 (2)	−0.002 (2)
C14	0.046 (3)	0.037 (2)	0.041 (3)	−0.002 (2)	0.007 (2)	0.002 (2)
C15	0.060 (3)	0.046 (3)	0.043 (3)	0.003 (3)	0.019 (2)	0.012 (2)
C16	0.055 (3)	0.046 (3)	0.043 (3)	0.007 (2)	0.023 (2)	0.007 (2)
C17	0.041 (3)	0.033 (2)	0.033 (2)	−0.002 (2)	0.0049 (19)	−0.0004 (18)
C18	0.062 (3)	0.048 (3)	0.030 (2)	0.006 (2)	0.011 (2)	0.003 (2)
C19	0.059 (3)	0.048 (3)	0.039 (3)	0.012 (3)	0.013 (2)	−0.002 (2)
C20	0.063 (3)	0.055 (3)	0.033 (2)	0.013 (3)	0.020 (2)	0.006 (2)
C21	0.061 (3)	0.049 (3)	0.037 (2)	0.015 (3)	0.019 (2)	0.002 (2)
C22	0.054 (3)	0.040 (3)	0.034 (2)	0.002 (2)	0.018 (2)	0.0008 (19)

Geometric parameters (Å, º) top

Hg1—N4ⁱ	2.326 (4)	C8—H8B	0.9600
Hg1—N4	2.326 (4)	C8—H8C	0.9600
Hg1—I1ⁱ	2.7277 (4)	C9—C10	1.499 (8)
Hg1—I1	2.7277 (4)	C9—H9A	0.9700
N1—C2	1.135 (10)	C9—H9B	0.9700
N2—C1	1.135 (10)	C10—C11	1.351 (7)
N3—C22	1.353 (6)	C10—C12	1.451 (7)
N3—C20	1.371 (6)	C11—H11	0.9300
N3—C17	1.430 (6)	C12—C13	1.328 (7)
N4—C22	1.311 (6)	C12—H12	0.9300
N4—C21	1.366 (6)	C13—C14	1.466 (7)
C1—C3	1.435 (10)	C13—H13	0.9300
C2—C3	1.429 (9)	C14—C19	1.389 (7)
C3—C4	1.362 (8)	C14—C15	1.394 (8)
C4—C11	1.440 (7)	C15—C16	1.375 (7)
C4—C5	1.486 (8)	C15—H15	0.9300
C5—C6	1.525 (8)	C16—C17	1.380 (7)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—C18	1.384 (7)
C6—C8	1.527 (9)	C18—C19	1.383 (7)
C6—C9	1.529 (8)	C18—H18	0.9300
C6—C7	1.535 (9)	C19—H19	0.9300
C7—H7A	0.9600	C20—C21	1.348 (7)
C7—H7B	0.9600	C20—H20	0.9300
C7—H7C	0.9600	C21—H21	0.9300
C8—H8A	0.9600	C22—H22	0.9300

N4ⁱ—Hg1—N4	100.90 (19)	C10—C9—H9A	108.8
N4ⁱ—Hg1—I1ⁱ	122.15 (10)	C6—C9—H9A	108.8
N4—Hg1—I1ⁱ	97.07 (10)	C10—C9—H9B	108.8
N4ⁱ—Hg1—I1	97.07 (10)	C6—C9—H9B	108.8
N4—Hg1—I1	122.15 (10)	H9A—C9—H9B	107.7
I1ⁱ—Hg1—I1	118.08 (2)	C11—C10—C12	119.1 (5)
C22—N3—C20	106.1 (4)	C11—C10—C9	120.6 (5)
C22—N3—C17	127.2 (4)	C12—C10—C9	120.3 (5)
C20—N3—C17	126.6 (4)	C10—C11—C4	122.4 (5)
C22—N4—C21	106.1 (4)	C10—C11—H11	118.8
C22—N4—Hg1	131.2 (3)	C4—C11—H11	118.8
C21—N4—Hg1	122.6 (3)	C13—C12—C10	125.7 (5)
N2—C1—C3	178.8 (10)	C13—C12—H12	117.1
N1—C2—C3	179.6 (10)	C10—C12—H12	117.1
C4—C3—C2	122.2 (6)	C12—C13—C14	127.0 (5)
C4—C3—C1	122.5 (5)	C12—C13—H13	116.5
C2—C3—C1	115.3 (6)	C14—C13—H13	116.5
C3—C4—C11	120.2 (5)	C19—C14—C15	117.0 (5)
C3—C4—C5	121.4 (5)	C19—C14—C13	118.8 (5)
C11—C4—C5	118.3 (5)	C15—C14—C13	124.1 (5)
C4—C5—C6	113.7 (5)	C16—C15—C14	121.6 (5)
C4—C5—H5A	108.8	C16—C15—H15	119.2
C6—C5—H5A	108.8	C14—C15—H15	119.2
C4—C5—H5B	108.8	C15—C16—C17	120.2 (5)
C6—C5—H5B	108.8	C15—C16—H16	119.9
H5A—C5—H5B	107.7	C17—C16—H16	119.9
C5—C6—C8	108.5 (5)	C16—C17—C18	119.8 (5)
C5—C6—C9	108.6 (5)	C16—C17—N3	120.5 (4)
C8—C6—C9	109.8 (5)	C18—C17—N3	119.7 (4)
C5—C6—C7	109.9 (5)	C19—C18—C17	119.2 (5)
C8—C6—C7	110.0 (6)	C19—C18—H18	120.4
C9—C6—C7	110.0 (5)	C17—C18—H18	120.4
C6—C7—H7A	109.5	C18—C19—C14	122.2 (5)
C6—C7—H7B	109.5	C18—C19—H19	118.9
H7A—C7—H7B	109.5	C14—C19—H19	118.9
C6—C7—H7C	109.5	C21—C20—N3	106.9 (4)
H7A—C7—H7C	109.5	C21—C20—H20	126.5
H7B—C7—H7C	109.5	N3—C20—H20	126.5
C6—C8—H8A	109.5	C20—C21—N4	109.4 (4)
C6—C8—H8B	109.5	C20—C21—H21	125.3
H8A—C8—H8B	109.5	N4—C21—H21	125.3
C6—C8—H8C	109.5	N4—C22—N3	111.4 (4)
H8A—C8—H8C	109.5	N4—C22—H22	124.3
H8B—C8—H8C	109.5	N3—C22—H22	124.3
C10—C9—C6	113.8 (5)

N4ⁱ—Hg1—N4—C22	−46.1 (4)	C11—C10—C12—C13	174.5 (5)
I1ⁱ—Hg1—N4—C22	−170.9 (4)	C9—C10—C12—C13	−5.0 (8)
I1—Hg1—N4—C22	59.5 (5)	C10—C12—C13—C14	178.3 (5)
N4ⁱ—Hg1—N4—C21	134.9 (4)	C12—C13—C14—C19	−177.6 (5)
I1ⁱ—Hg1—N4—C21	10.1 (4)	C12—C13—C14—C15	−0.3 (9)
I1—Hg1—N4—C21	−119.5 (4)	C19—C14—C15—C16	−1.1 (8)
N1—C2—C3—C4	113 (100)	C13—C14—C15—C16	−178.4 (5)
N1—C2—C3—C1	−67 (100)	C14—C15—C16—C17	0.3 (8)
N2—C1—C3—C4	−128 (47)	C15—C16—C17—C18	0.7 (8)
N2—C1—C3—C2	51 (48)	C15—C16—C17—N3	−179.3 (5)
C2—C3—C4—C11	−178.3 (6)	C22—N3—C17—C16	175.5 (5)
C1—C3—C4—C11	0.8 (10)	C20—N3—C17—C16	−1.7 (8)
C2—C3—C4—C5	−1.2 (10)	C22—N3—C17—C18	−4.6 (7)
C1—C3—C4—C5	177.9 (7)	C20—N3—C17—C18	178.2 (5)
C3—C4—C5—C6	154.3 (6)	C16—C17—C18—C19	−1.0 (8)
C11—C4—C5—C6	−28.5 (7)	N3—C17—C18—C19	179.1 (5)
C4—C5—C6—C8	171.2 (6)	C17—C18—C19—C14	0.1 (9)
C4—C5—C6—C9	51.9 (6)	C15—C14—C19—C18	0.9 (8)
C4—C5—C6—C7	−68.5 (7)	C13—C14—C19—C18	178.4 (5)
C5—C6—C9—C10	−49.4 (6)	C22—N3—C20—C21	0.4 (6)
C8—C6—C9—C10	−167.9 (5)	C17—N3—C20—C21	178.1 (5)
C7—C6—C9—C10	70.9 (6)	N3—C20—C21—N4	−0.5 (7)
C6—C9—C10—C11	23.9 (7)	C22—N4—C21—C20	0.4 (6)
C6—C9—C10—C12	−156.7 (5)	Hg1—N4—C21—C20	179.7 (4)
C12—C10—C11—C4	−177.0 (5)	C21—N4—C22—N3	−0.2 (6)
C9—C10—C11—C4	2.4 (8)	Hg1—N4—C22—N3	−179.3 (3)
C3—C4—C11—C10	177.1 (6)	C20—N3—C22—N4	−0.2 (6)
C5—C4—C11—C10	−0.1 (8)	C17—N3—C22—N4	−177.8 (4)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱⁱ	0.93	2.70	3.541 (15)	151
C18—H18···I1ⁱⁱⁱ	0.93	3.09	3.864 (5)	142

Symmetry codes: (ii) x, −y+3, z+1/2; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2ⁱ	0.93	2.70	3.541 (15)	151
C18—H18···I1ⁱⁱ	0.93	3.09	3.864 (5)	142

Symmetry codes: (i) x, −y+3, z+1/2; (ii) x, y+1, z.

Acknowledgements

This work was supported by the Program for New Century Excellent Talents in University (China), the Doctoral Program Foundation of the Ministry of Education of China (20113401110004), the National Natural Science Foundation of China (21271003 and 21271004), the Natural Science Foundation of the Education Committee of Anhui Province (KJ2012A024), the Natural Science Foundation of Anhui Province (1208085MB22) and the 211 Project of Anhui University

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