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

In the title complex, [HgI2(C21H19N5)2], the Hg(II) ion is located on a twofold rotation axis and is coordinated by two I atoms and two N atoms from two (E)-2-{5,5-di-methyl-3-[4-(1H-1,2,4-triazol-1-yl)styr-yl]cyclo-hex-2-enyl-idene}malono-nitrile ligands in a distorted tetra-hedral geometry. In the crystal, the mol-ecules are linked by inter-molecular π-π inter-actions between the triazole and benzene rings [centroid-centroid distance = 3.794 (3) Å] into a band extending in [010]. These bands are further connected by C-H⋯N hydrogen bonds into a two-dimensional network parallel to (100).

Related literature

For background to metal-organic complexes, see: Haneda et al. (2007 ▶); Li et al. (2006 ▶); Liu et al. (2010 ▶, 2011 ▶); Satapathy et al. (2012 ▶); Sun et al. (2012 ▶). For the organic ligand of the title compound, see: Zheng et al. (2013 ▶). For related structures, see: Jin, Wang et al. (2013 ▶); Jin, Zhang et al. (2013 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

[HgI2(C21H19N5)2]

M = 1137.21

Monoclinic,

a = 38.9622 (16) Å

b = 5.5684 (12) Å

c = 21.9564 (14) Å

β = 117.738 (2)°

V = 4216.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 5.16 mm−1

T = 291 K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.307, T max = 0.457

14961 measured reflections

4078 independent reflections

3384 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.071

S = 1.01

4078 reflections

251 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S160053681302518X/hy2634sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302518X/hy2634Isup2.hkl

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

[HgI2(C21H19N5)2]	F(000) = 2184
Mr = 1137.21	Dx = 1.792 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 38.9622 (16) Å	Cell parameters from 3126 reflections
b = 5.5684 (12) Å	θ = 2.1–23.6°
c = 21.9564 (14) Å	µ = 5.16 mm−1
β = 117.738 (2)°	T = 291 K
V = 4216.2 (10) Å3	Needle, yellow
Z = 4	0.30 × 0.20 × 0.18 mm

Bruker APEX CCD diffractometer	4078 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −47→47
Tmin = 0.307, Tmax = 0.457	k = −6→6
14961 measured reflections	l = −26→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.04P)2 + 0.22P] where P = (Fo2 + 2Fc2)/3
4078 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.52 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.

	x	y	z	Uiso*/Ueq
Hg1	0.0000	1.49817 (4)	0.7500	0.04679 (9)
I1	0.06739 (2)	1.65983 (6)	0.84809 (2)	0.06479 (11)
C19	0.11064 (13)	0.4748 (8)	0.6784 (2)	0.0541 (11)
H19	0.1329	0.4209	0.7164	0.065*
C15	0.06588 (13)	0.4500 (8)	0.5599 (2)	0.0560 (11)
H15	0.0575	0.3788	0.5170	0.067*
C16	0.04479 (12)	0.6381 (8)	0.5667 (2)	0.0540 (10)
H16	0.0227	0.6937	0.5288	0.065*
N5	0.01215 (9)	1.2154 (6)	0.67843 (16)	0.0452 (7)
N3	0.03392 (9)	0.9312 (6)	0.63805 (16)	0.0409 (7)
C13	0.12305 (12)	0.1699 (7)	0.6110 (2)	0.0485 (9)
H13	0.1406	0.1013	0.6525	0.058*
C21	−0.01308 (12)	1.1596 (8)	0.6130 (2)	0.0590 (11)
H21	−0.0370	1.2354	0.5892	0.071*
C20	0.04150 (12)	1.0708 (7)	0.6927 (2)	0.0447 (9)
H20	0.0641	1.0659	0.7344	0.054*
C17	0.05698 (10)	0.7431 (6)	0.63072 (19)	0.0401 (8)
C14	0.09914 (11)	0.3646 (7)	0.6153 (2)	0.0439 (9)
N4	−0.00144 (11)	0.9900 (6)	0.58534 (19)	0.0614 (10)
C18	0.08964 (12)	0.6650 (8)	0.6862 (2)	0.0528 (10)
H18	0.0979	0.7374	0.7290	0.063*
C10	0.14855 (11)	−0.1065 (7)	0.5526 (2)	0.0430 (9)
C9	0.17746 (11)	−0.2203 (7)	0.61823 (19)	0.0481 (9)
H9A	0.1640	−0.3332	0.6333	0.058*
H9B	0.1885	−0.0966	0.6532	0.058*
C11	0.14662 (11)	−0.1692 (7)	0.4915 (2)	0.0468 (9)
H11	0.1295	−0.0878	0.4520	0.056*
C12	0.12256 (12)	0.0798 (7)	0.5548 (2)	0.0490 (10)
H12	0.1040	0.1402	0.5129	0.059*
C6	0.21068 (11)	−0.3527 (6)	0.61357 (19)	0.0451 (9)
C5	0.19376 (13)	−0.5051 (6)	0.5484 (2)	0.0504 (10)
H5A	0.2147	−0.5826	0.5437	0.061*
H5B	0.1775	−0.6298	0.5524	0.061*
C4	0.17029 (11)	−0.3582 (7)	0.4857 (2)	0.0448 (9)
C1	0.19109 (13)	−0.6083 (9)	0.4172 (2)	0.0556 (10)
C2	0.17018 (12)	−0.4045 (8)	0.4249 (2)	0.0493 (10)
C3	0.14937 (13)	−0.2621 (9)	0.3649 (2)	0.0566 (11)
N2	0.13295 (13)	−0.1425 (8)	0.3170 (2)	0.0772 (12)
N1	0.20731 (13)	−0.7689 (8)	0.4121 (2)	0.0824 (13)
C8	0.24041 (12)	−0.1776 (7)	0.6121 (2)	0.0580 (11)
H8A	0.2609	−0.2658	0.6095	0.087*
H8B	0.2510	−0.0819	0.6531	0.087*
H8C	0.2280	−0.0748	0.5726	0.087*
C7	0.23118 (16)	−0.5185 (7)	0.6758 (3)	0.0698 (14)
H7A	0.2131	−0.6351	0.6761	0.105*
H7B	0.2411	−0.4252	0.7173	0.105*
H7C	0.2522	−0.5992	0.6732	0.105*

	U11	U22	U33	U12	U13	U23
Hg1	0.05187 (14)	0.04752 (14)	0.04360 (14)	0.000	0.02444 (11)	0.000
I1	0.0631 (2)	0.0737 (2)	0.05467 (19)	−0.01842 (15)	0.02500 (15)	−0.00968 (15)
C19	0.056 (3)	0.069 (3)	0.043 (2)	0.019 (2)	0.027 (2)	0.012 (2)
C15	0.053 (3)	0.064 (3)	0.050 (3)	0.000 (2)	0.023 (2)	−0.023 (2)
C16	0.044 (2)	0.066 (3)	0.046 (2)	0.008 (2)	0.0154 (18)	−0.016 (2)
N5	0.0489 (19)	0.0457 (18)	0.0442 (18)	0.0023 (15)	0.0242 (16)	−0.0050 (15)
N3	0.0427 (18)	0.0461 (17)	0.0376 (17)	0.0000 (14)	0.0219 (15)	−0.0028 (14)
C13	0.056 (2)	0.045 (2)	0.053 (2)	0.0027 (18)	0.032 (2)	0.0038 (19)
C21	0.048 (2)	0.077 (3)	0.048 (2)	0.014 (2)	0.019 (2)	−0.007 (2)
C20	0.049 (2)	0.047 (2)	0.039 (2)	0.0000 (18)	0.0210 (18)	−0.0038 (17)
C17	0.046 (2)	0.0409 (19)	0.043 (2)	−0.0022 (17)	0.0285 (18)	−0.0026 (17)
C14	0.049 (2)	0.045 (2)	0.049 (2)	−0.0011 (18)	0.0314 (19)	−0.0004 (18)
N4	0.050 (2)	0.082 (3)	0.044 (2)	0.0147 (18)	0.0156 (17)	−0.0155 (18)
C18	0.064 (3)	0.065 (3)	0.035 (2)	0.016 (2)	0.028 (2)	−0.001 (2)
C10	0.047 (2)	0.0361 (19)	0.051 (2)	−0.0018 (17)	0.0268 (19)	−0.0027 (18)
C9	0.057 (2)	0.041 (2)	0.051 (2)	−0.0002 (18)	0.029 (2)	−0.0021 (19)
C11	0.050 (2)	0.045 (2)	0.045 (2)	0.0068 (18)	0.0219 (19)	−0.0007 (18)
C12	0.048 (2)	0.048 (2)	0.055 (3)	0.0043 (19)	0.027 (2)	−0.004 (2)
C6	0.055 (2)	0.0315 (19)	0.045 (2)	0.0024 (17)	0.0202 (18)	0.0003 (17)
C5	0.061 (3)	0.032 (2)	0.061 (3)	0.0023 (18)	0.031 (2)	−0.0009 (19)
C4	0.042 (2)	0.042 (2)	0.053 (2)	−0.0049 (17)	0.0240 (18)	−0.0077 (18)
C1	0.056 (3)	0.056 (3)	0.060 (3)	−0.002 (2)	0.031 (2)	−0.014 (2)
C2	0.047 (2)	0.045 (2)	0.054 (3)	−0.0012 (19)	0.023 (2)	−0.012 (2)
C3	0.053 (3)	0.070 (3)	0.045 (3)	0.000 (2)	0.021 (2)	−0.018 (2)
N2	0.081 (3)	0.087 (3)	0.055 (3)	0.007 (2)	0.024 (2)	−0.007 (2)
N1	0.082 (3)	0.075 (3)	0.103 (3)	0.003 (2)	0.053 (3)	−0.028 (3)
C8	0.051 (2)	0.047 (2)	0.071 (3)	−0.0008 (19)	0.024 (2)	−0.002 (2)
C7	0.091 (4)	0.048 (3)	0.062 (3)	0.014 (2)	0.028 (3)	0.009 (2)

Hg1—N5	2.422 (3)	C10—C9	1.495 (5)
Hg1—I1	2.6606 (8)	C9—C6	1.533 (5)
C19—C14	1.385 (6)	C9—H9A	0.9700
C19—C18	1.397 (5)	C9—H9B	0.9700
C19—H19	0.9300	C11—C4	1.444 (5)
C15—C16	1.381 (5)	C11—H11	0.9300
C15—C14	1.384 (6)	C12—H12	0.9300
C15—H15	0.9300	C6—C5	1.524 (5)
C16—C17	1.386 (5)	C6—C8	1.526 (5)
C16—H16	0.9300	C6—C7	1.531 (6)
N5—C20	1.312 (5)	C5—C4	1.494 (6)
N5—C21	1.346 (5)	C5—H5A	0.9700
N3—C20	1.342 (5)	C5—H5B	0.9700
N3—N4	1.364 (5)	C4—C2	1.357 (5)
N3—C17	1.437 (5)	C1—N1	1.131 (5)
C13—C12	1.324 (5)	C1—C2	1.452 (6)
C13—C14	1.461 (5)	C2—C3	1.424 (6)
C13—H13	0.9300	C3—N2	1.153 (5)
C21—N4	1.313 (5)	C8—H8A	0.9600
C21—H21	0.9300	C8—H8B	0.9600
C20—H20	0.9300	C8—H8C	0.9600
C17—C18	1.360 (5)	C7—H7A	0.9600
C18—H18	0.9300	C7—H7B	0.9600
C10—C11	1.354 (5)	C7—H7C	0.9600
C10—C12	1.466 (5)
N5i—Hg1—N5	98.89 (15)	C10—C9—H9A	108.6
N5i—Hg1—I1	96.43 (8)	C6—C9—H9A	108.6
N5—Hg1—I1	109.14 (7)	C10—C9—H9B	108.6
N5i—Hg1—I1i	109.15 (7)	C6—C9—H9B	108.6
N5—Hg1—I1i	96.43 (8)	H9A—C9—H9B	107.5
I1—Hg1—I1i	140.450 (19)	C10—C11—C4	122.2 (4)
C14—C19—C18	121.6 (4)	C10—C11—H11	118.9
C14—C19—H19	119.2	C4—C11—H11	118.9
C18—C19—H19	119.2	C13—C12—C10	126.0 (4)
C16—C15—C14	121.7 (4)	C13—C12—H12	117.0
C16—C15—H15	119.1	C10—C12—H12	117.0
C14—C15—H15	119.1	C5—C6—C8	109.7 (3)
C15—C16—C17	119.3 (4)	C5—C6—C7	108.7 (3)
C15—C16—H16	120.4	C8—C6—C7	108.6 (4)
C17—C16—H16	120.4	C5—C6—C9	108.7 (3)
C20—N5—C21	103.6 (3)	C8—C6—C9	111.5 (3)
C20—N5—Hg1	131.0 (3)	C7—C6—C9	109.6 (4)
C21—N5—Hg1	125.2 (3)	C4—C5—C6	111.9 (3)
C20—N3—N4	109.6 (3)	C4—C5—H5A	109.2
C20—N3—C17	129.3 (3)	C6—C5—H5A	109.2
N4—N3—C17	121.1 (3)	C4—C5—H5B	109.2
C12—C13—C14	127.5 (4)	C6—C5—H5B	109.2
C12—C13—H13	116.3	H5A—C5—H5B	107.9
C14—C13—H13	116.3	C2—C4—C11	121.1 (4)
N4—C21—N5	115.0 (4)	C2—C4—C5	121.6 (4)
N4—C21—H21	122.5	C11—C4—C5	117.3 (3)
N5—C21—H21	122.5	N1—C1—C2	178.8 (5)
N5—C20—N3	109.7 (4)	C4—C2—C3	122.9 (4)
N5—C20—H20	125.1	C4—C2—C1	121.2 (4)
N3—C20—H20	125.1	C3—C2—C1	115.9 (4)
C18—C17—C16	120.7 (3)	N2—C3—C2	178.6 (5)
C18—C17—N3	120.3 (3)	C6—C8—H8A	109.5
C16—C17—N3	119.0 (3)	C6—C8—H8B	109.5
C15—C14—C19	117.5 (3)	H8A—C8—H8B	109.5
C15—C14—C13	124.2 (4)	C6—C8—H8C	109.5
C19—C14—C13	118.3 (4)	H8A—C8—H8C	109.5
C21—N4—N3	102.1 (3)	H8B—C8—H8C	109.5
C17—C18—C19	119.2 (4)	C6—C7—H7A	109.5
C17—C18—H18	120.4	C6—C7—H7B	109.5
C19—C18—H18	120.4	H7A—C7—H7B	109.5
C11—C10—C12	119.6 (4)	C6—C7—H7C	109.5
C11—C10—C9	121.0 (3)	H7A—C7—H7C	109.5
C12—C10—C9	119.4 (3)	H7B—C7—H7C	109.5
C10—C9—C6	114.9 (3)
C14—C15—C16—C17	−0.6 (7)	N3—C17—C18—C19	177.2 (3)
C20—N5—C21—N4	−0.1 (5)	C14—C19—C18—C17	0.4 (6)
Hg1—N5—C21—N4	−175.7 (3)	C11—C10—C9—C6	16.2 (5)
C21—N5—C20—N3	−0.8 (4)	C12—C10—C9—C6	−162.3 (3)
Hg1—N5—C20—N3	174.5 (2)	C12—C10—C11—C4	−177.3 (4)
N4—N3—C20—N5	1.4 (5)	C9—C10—C11—C4	4.1 (6)
C17—N3—C20—N5	−178.0 (3)	C14—C13—C12—C10	176.2 (4)
C15—C16—C17—C18	1.0 (6)	C11—C10—C12—C13	−175.1 (4)
C15—C16—C17—N3	−177.2 (4)	C9—C10—C12—C13	3.4 (6)
C20—N3—C17—C18	8.1 (6)	C10—C9—C6—C5	−45.2 (4)
N4—N3—C17—C18	−171.2 (4)	C10—C9—C6—C8	75.8 (4)
C20—N3—C17—C16	−173.8 (4)	C10—C9—C6—C7	−163.9 (4)
N4—N3—C17—C16	6.9 (5)	C8—C6—C5—C4	−66.4 (4)
C16—C15—C14—C19	0.1 (6)	C7—C6—C5—C4	175.1 (4)
C16—C15—C14—C13	−178.7 (4)	C9—C6—C5—C4	55.8 (4)
C18—C19—C14—C15	0.0 (6)	C10—C11—C4—C2	−174.5 (4)
C18—C19—C14—C13	178.9 (4)	C10—C11—C4—C5	7.5 (6)
C12—C13—C14—C15	15.6 (7)	C6—C5—C4—C2	143.5 (4)
C12—C13—C14—C19	−163.3 (4)	C6—C5—C4—C11	−38.5 (5)
N5—C21—N4—N3	0.9 (5)	C11—C4—C2—C3	4.7 (6)
C20—N3—N4—C21	−1.3 (4)	C5—C4—C2—C3	−177.4 (4)
C17—N3—N4—C21	178.1 (3)	C11—C4—C2—C1	−174.2 (4)
C16—C17—C18—C19	−0.9 (6)	C5—C4—C2—C1	3.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2ii	0.93	2.48	3.354 (7)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N2i	0.93	2.48	3.354 (7)	157

Symmetry code: (i) .