Bis((E)-2-{3-[4-(1H-imidazol-1-yl-κN (3))styr-yl]-5,5-di-methyl-cyclo-hex-2-enyl-idene}malono-nitrile)-diiodido-mercury(II).

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 tetra-hedral geometry. In the crystal, C-H⋯I inter-actions link the mol-ecules into chains extending in [010], which are further linked into sheets parallel to (100) through C-H⋯N hydrogen bonding inter-actions.

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 = 1135.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.04

3889 reflections

251 parameters

H-atom parameters constrained

Δρmax = 2.28 e Å−3

Δρmin = −1.86 e Å−3

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.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536813025191/cq2006sup1.cif

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

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

[HgI2(C22H20N4)2]	Z = 2
Mr = 1135.23	F(000) = 1092
Monoclinic, P2/c	Dx = 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

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

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(Fo2) + (0.0496P)2 + 4.7641P] where P = (Fo2 + 2Fc2)/3
3889 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 2.28 e Å−3
0 restraints	Δρmin = −1.86 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	0.5000	−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*

	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)

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)

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

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) ; (ii) .