(4,4'-Dimethyl-2,2'-bipyridine-κN,N')diiodidomercury(II).

In the mol-ecule of the title compound, [HgI(2)(C(12)H(12)N(2))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from the 4,4'-dimethyl-2,2'-bipyridine ligand and by two I atoms. There is a π-π contact between the pyridine rings [centroid-centroid distance = 3.775 (6) Å].

Related literature

For related literature, see: Khalighi et al. (2008 ▶); Ahmadi et al. (2008 ▶); Khavasi et al. (2008 ▶); Freire et al. (1999 ▶); Chen et al. (2006 ▶); Htoon & Ladd (1976 ▶).

Experimental

Crystal data

[HgI2(C12H12N2)]

M = 638.63

Triclinic,

a = 8.4214 (9) Å

b = 9.8391 (10) Å

c = 10.2983 (10) Å

α = 69.383 (8)°

β = 88.448 (8)°

γ = 74.670 (8)°

V = 768.18 (14) Å3

Z = 2

Mo Kα radiation

μ = 14.02 mm−1

T = 298 (2) K

0.38 × 0.25 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.022, T max = 0.183

8874 measured reflections

4123 independent reflections

3467 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.159

S = 0.95

4123 reflections

155 parameters

H-atom parameters constrained

Δρmax = 1.95 e Å−3

Δρmin = −1.38 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028791/hk2525sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028791/hk2525Isup2.hkl

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

[HgI2(C12H12N2)]	Z = 2
Mr = 638.63	F(000) = 568
Triclinic, P1	Dx = 2.761 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4214 (9) Å	Cell parameters from 2145 reflections
b = 9.8391 (10) Å	θ = 2.1–29.2°
c = 10.2983 (10) Å	µ = 14.02 mm−1
α = 69.383 (8)°	T = 298 K
β = 88.448 (8)°	Block, colourless
γ = 74.670 (8)°	0.38 × 0.25 × 0.12 mm
V = 768.18 (14) Å3

Bruker SMART CCD area-detector diffractometer	4123 independent reflections
Radiation source: fine-focus sealed tube	3467 reflections with I > 2σ(I)
graphite	Rint = 0.091
φ and ω scans	θmax = 29.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.022, Tmax = 0.183	k = −13→13
8874 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.108P)2 + 1.3499P] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.002
4123 reflections	Δρmax = 1.95 e Å−3
155 parameters	Δρmin = −1.38 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (13)

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	0.31760 (5)	0.15247 (5)	0.30109 (4)	0.05970 (19)
I1	0.03155 (9)	0.31134 (10)	0.35551 (9)	0.0704 (2)
I2	0.63357 (8)	0.13618 (9)	0.35681 (7)	0.0594 (2)
N1	0.3481 (10)	0.2223 (10)	0.0514 (8)	0.0520 (16)
N2	0.2438 (12)	−0.0160 (12)	0.2073 (9)	0.0595 (19)
C1	0.3943 (12)	0.3461 (12)	−0.0232 (12)	0.058 (2)
H1	0.4209	0.4042	0.0227	0.069*
C2	0.4037 (14)	0.3905 (12)	−0.1657 (13)	0.064 (3)
H2	0.4374	0.4763	−0.2141	0.077*
C3	0.3630 (12)	0.3066 (10)	−0.2355 (10)	0.053 (2)
C4	0.368 (2)	0.3537 (19)	−0.3901 (13)	0.080 (4)
H4A	0.2607	0.3701	−0.4313	0.096*
H4B	0.4460	0.2758	−0.4127	0.096*
H4C	0.4015	0.4454	−0.4256	0.096*
C5	0.3166 (12)	0.1780 (10)	−0.1574 (9)	0.0512 (18)
H5	0.2901	0.1178	−0.2009	0.061*
C6	0.3098 (10)	0.1393 (10)	−0.0149 (9)	0.0461 (16)
C7	0.2537 (10)	0.0050 (9)	0.0721 (9)	0.0438 (15)
C8	0.2150 (11)	−0.0932 (10)	0.0177 (10)	0.0488 (17)
H8	0.2260	−0.0777	−0.0762	0.059*
C9	0.1602 (11)	−0.2137 (10)	0.1003 (11)	0.0525 (19)
C10	0.1200 (14)	−0.3201 (12)	0.0393 (13)	0.065 (2)
H10A	0.2170	−0.3670	0.0034	0.079*
H10B	0.0348	−0.2648	−0.0346	0.079*
H10C	0.0825	−0.3962	0.1103	0.079*
C11	0.1411 (15)	−0.2305 (14)	0.2394 (12)	0.065 (3)
H11	0.1004	−0.3078	0.2981	0.078*
C12	0.1831 (16)	−0.1319 (15)	0.2875 (11)	0.066 (3)
H12	0.1698	−0.1438	0.3805	0.079*

	U11	U22	U33	U12	U13	U23
Hg1	0.0532 (2)	0.0783 (3)	0.0614 (3)	−0.02592 (18)	0.01400 (15)	−0.0362 (2)
I1	0.0537 (4)	0.0824 (5)	0.0729 (4)	−0.0159 (3)	0.0167 (3)	−0.0280 (4)
I2	0.0539 (3)	0.0771 (4)	0.0543 (3)	−0.0294 (3)	0.0096 (2)	−0.0241 (3)
N1	0.056 (4)	0.058 (4)	0.049 (3)	−0.022 (3)	0.010 (3)	−0.022 (3)
N2	0.063 (5)	0.077 (5)	0.047 (4)	−0.029 (4)	0.011 (3)	−0.026 (4)
C1	0.054 (5)	0.052 (5)	0.074 (6)	−0.023 (4)	0.005 (4)	−0.025 (4)
C2	0.061 (5)	0.047 (5)	0.079 (7)	−0.021 (4)	0.010 (5)	−0.013 (4)
C3	0.054 (5)	0.044 (4)	0.056 (5)	−0.013 (3)	0.006 (4)	−0.012 (3)
C4	0.089 (9)	0.089 (9)	0.056 (5)	−0.033 (7)	0.013 (5)	−0.013 (6)
C5	0.057 (5)	0.048 (4)	0.048 (4)	−0.015 (4)	0.009 (3)	−0.016 (3)
C6	0.041 (4)	0.044 (4)	0.052 (4)	−0.011 (3)	0.013 (3)	−0.017 (3)
C7	0.039 (3)	0.042 (3)	0.048 (4)	−0.010 (3)	0.008 (3)	−0.016 (3)
C8	0.047 (4)	0.048 (4)	0.053 (4)	−0.014 (3)	0.012 (3)	−0.020 (3)
C9	0.043 (4)	0.048 (4)	0.061 (5)	−0.012 (3)	0.004 (3)	−0.014 (3)
C10	0.067 (5)	0.049 (5)	0.078 (6)	−0.014 (4)	0.010 (5)	−0.021 (4)
C11	0.071 (6)	0.070 (6)	0.060 (5)	−0.040 (5)	0.007 (5)	−0.013 (5)
C12	0.075 (7)	0.079 (7)	0.050 (4)	−0.040 (5)	0.015 (4)	−0.017 (4)

Hg1—I1	2.6671 (9)	C6—N1	1.334 (12)
Hg1—I2	2.6885 (8)	C6—C7	1.498 (12)
N1—Hg1	2.442 (8)	C7—N2	1.337 (12)
N2—Hg1	2.402 (10)	C7—C8	1.383 (13)
C1—N1	1.342 (13)	C8—C9	1.378 (13)
C1—C2	1.382 (17)	C8—H8	0.9300
C1—H1	0.9300	C9—C11	1.392 (16)
C2—C3	1.377 (17)	C9—C10	1.506 (16)
C2—H2	0.9300	C10—H10A	0.9600
C3—C5	1.389 (13)	C10—H10B	0.9600
C3—C4	1.497 (16)	C10—H10C	0.9600
C4—H4A	0.9600	C11—C12	1.357 (18)
C4—H4B	0.9600	C11—H11	0.9300
C4—H4C	0.9600	C12—N2	1.366 (15)
C5—C6	1.384 (12)	C12—H12	0.9300
C5—H5	0.9300
I1—Hg1—I2	132.56 (3)	C6—C5—C3	120.2 (9)
N1—Hg1—I1	111.9 (2)	C6—C5—H5	119.7
N1—Hg1—I2	92.87 (19)	C3—C5—H5	120.2
N2—Hg1—N1	67.3 (3)	N1—C6—C5	121.6 (8)
N2—Hg1—I1	104.9 (2)	N1—C6—C7	116.6 (8)
N2—Hg1—I2	122.2 (2)	C5—C6—C7	121.7 (8)
C1—N1—Hg1	122.2 (7)	N2—C7—C8	121.2 (8)
C6—N1—Hg1	119.2 (6)	N2—C7—C6	116.1 (8)
C6—N1—C1	118.6 (8)	C8—C7—C6	122.6 (8)
C7—N2—Hg1	120.8 (7)	C9—C8—C7	121.0 (9)
C7—N2—C12	117.4 (9)	C9—C8—H8	119.4
C12—N2—Hg1	121.7 (7)	C7—C8—H8	119.6
N1—C1—C2	122.5 (10)	C8—C9—C11	117.7 (10)
N1—C1—H1	118.7	C8—C9—C10	120.2 (10)
C2—C1—H1	118.8	C11—C9—C10	122.1 (9)
C3—C2—C1	119.5 (10)	C9—C10—H10A	109.2
C3—C2—H2	120.1	C9—C10—H10B	109.6
C1—C2—H2	120.4	H10A—C10—H10B	109.5
C2—C3—C5	117.6 (10)	C9—C10—H10C	109.6
C2—C3—C4	120.8 (11)	H10A—C10—H10C	109.5
C5—C3—C4	121.6 (11)	H10B—C10—H10C	109.5
C3—C4—H4A	109.3	C12—C11—C9	118.7 (10)
C3—C4—H4B	109.5	C12—C11—H11	120.7
H4A—C4—H4B	109.5	C9—C11—H11	120.6
C3—C4—H4C	109.6	N2—C12—C11	123.8 (10)
H4A—C4—H4C	109.5	N2—C12—H12	118.1
H4B—C4—H4C	109.5	C11—C12—H12	118.2
C1—N1—Hg1—I1	79.7 (8)	C5—C6—N1—Hg1	176.7 (6)
C1—N1—Hg1—I2	−58.9 (7)	C7—C6—N1—Hg1	−1.4 (10)
C1—N1—Hg1—N2	177.2 (8)	C5—C6—N1—C1	−0.1 (13)
C6—N1—Hg1—I1	−96.9 (7)	C7—C6—N1—C1	−178.1 (8)
C6—N1—Hg1—I2	124.5 (7)	N1—C6—C7—N2	1.6 (11)
C6—N1—Hg1—N2	0.6 (7)	C5—C6—C7—N2	−176.5 (9)
C7—N2—Hg1—I1	108.1 (7)	N1—C6—C7—C8	−178.0 (8)
C7—N2—Hg1—I2	−78.2 (8)	C5—C6—C7—C8	4.0 (12)
C7—N2—Hg1—N1	0.2 (7)	C6—C7—N2—Hg1	−1.0 (10)
C12—N2—Hg1—I1	−68.7 (9)	C8—C7—N2—Hg1	178.6 (6)
C12—N2—Hg1—I2	104.9 (9)	C6—C7—N2—C12	176.0 (9)
C12—N2—Hg1—N1	−176.6 (10)	C8—C7—N2—C12	−4.5 (14)
C2—C1—N1—C6	−0.1 (15)	N2—C7—C8—C9	1.9 (13)
C2—C1—N1—Hg1	−176.7 (8)	C6—C7—C8—C9	−178.6 (8)
N1—C1—C2—C3	0.7 (16)	C7—C8—C9—C11	1.7 (13)
C1—C2—C3—C5	−1.2 (16)	C7—C8—C9—C10	−179.5 (8)
C1—C2—C3—C4	178.6 (11)	C8—C9—C11—C12	−2.5 (16)
C2—C3—C5—C6	1.1 (14)	C10—C9—C11—C12	178.7 (11)
C4—C3—C5—C6	−178.7 (10)	C9—C11—C12—N2	−0.1 (19)
C3—C5—C6—N1	−0.5 (14)	C11—C12—N2—Hg1	−179.4 (10)
C3—C5—C6—C7	177.4 (8)	C11—C12—N2—C7	3.6 (18)

Hg1—I1	2.6671 (9)
Hg1—I2	2.6885 (8)
N1—Hg1	2.442 (8)
N2—Hg1	2.402 (10)

I1—Hg1—I2	132.56 (3)
N1—Hg1—I1	111.9 (2)
N1—Hg1—I2	92.87 (19)
N2—Hg1—N1	67.3 (3)
N2—Hg1—I1	104.9 (2)
N2—Hg1—I2	122.2 (2)