(5,5'-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 5,5'-dimethyl-2,2'-bipyridine and two I atoms. There is a π-π contact between pyridine rings of adjacent molecules [centroid-centroid distance = 3.723 (5) Å].

Related literature

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

Experimental

Crystal data

[HgI2(C12H12N2)]

M = 638.63

Orthorhombic,

a = 15.0325 (8) Å

b = 15.0654 (8) Å

c = 14.0579 (10) Å

V = 3183.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 13.53 mm−1

T = 298 (2) K

0.35 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005) ▶] T min = 0.015, T max = 0.075

23007 measured reflections

4306 independent reflections

3418 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.124

S = 1.19

4306 reflections

154 parameters

H-atom parameters constrained

Δρmax = 1.44 e Å−3

Δρmin = −1.51 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. DOI: 10.1107/S160053680802953X/hk2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802953X/hk2531Isup2.hkl

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

[HgI2(C12H12N2)]	F(000) = 2272
Mr = 638.63	Dx = 2.665 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1768 reflections
a = 15.0325 (8) Å	θ = 2.4–29.3°
b = 15.0654 (8) Å	µ = 13.53 mm−1
c = 14.0579 (10) Å	T = 298 K
V = 3183.7 (3) Å3	Prism, colorless
Z = 8	0.35 × 0.31 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	3418 reflections with I > 2σ(I)
graphite	Rint = 0.083
φ and ω scans	θmax = 29.3°, θmin = 2.4°
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED32; Stoe& Cie, 2005)	h = −20→19
Tmin = 0.015, Tmax = 0.075	k = −20→17
23007 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0347P)2 + 17.4498P] where P = (Fo2 + 2Fc2)/3
4306 reflections	(Δ/σ)max = 0.010
154 parameters	Δρmax = 1.44 e Å−3
0 restraints	Δρmin = −1.51 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	0.11964 (2)	0.71065 (2)	0.60202 (3)	0.05197 (12)
I1	0.00810 (7)	0.80915 (5)	0.50004 (7)	0.0859 (3)
I2	0.25140 (5)	0.76000 (5)	0.71769 (6)	0.0687 (2)
N1	0.1696 (4)	0.5812 (5)	0.5214 (5)	0.0403 (14)
N2	0.0387 (4)	0.5836 (4)	0.6554 (5)	0.0381 (13)
C1	0.2371 (5)	0.5833 (6)	0.4598 (6)	0.0463 (18)
H1	0.2633	0.6377	0.4460	0.056*
C2	0.2697 (6)	0.5082 (7)	0.4155 (6)	0.049 (2)
C3	0.3485 (8)	0.5156 (9)	0.3481 (9)	0.077 (3)
H3A	0.3986	0.5399	0.3816	0.093*
H3B	0.3333	0.5538	0.2959	0.093*
H3C	0.3635	0.4578	0.3243	0.093*
C4	0.2299 (7)	0.4279 (7)	0.4391 (8)	0.063 (3)
H4	0.2506	0.3755	0.4121	0.076*
C5	0.1604 (7)	0.4257 (6)	0.5019 (7)	0.053 (2)
H5	0.1324	0.3723	0.5162	0.063*
C6	0.1322 (5)	0.5044 (5)	0.5440 (5)	0.0387 (16)
C7	0.0586 (5)	0.5057 (5)	0.6156 (5)	0.0378 (15)
C8	0.0140 (6)	0.4291 (6)	0.6412 (7)	0.054 (2)
H8	0.0270	0.3754	0.6118	0.065*
C9	−0.0503 (6)	0.4341 (6)	0.7113 (7)	0.054 (2)
H9	−0.0805	0.3829	0.7297	0.065*
C10	−0.0703 (6)	0.5135 (6)	0.7542 (6)	0.0477 (19)
C11	−0.1370 (7)	0.5206 (8)	0.8337 (8)	0.069 (3)
H11A	−0.1831	0.5615	0.8159	0.083*
H11B	−0.1078	0.5417	0.8901	0.083*
H11C	−0.1625	0.4633	0.8458	0.083*
C12	−0.0244 (5)	0.5873 (6)	0.7226 (6)	0.0465 (18)
H12	−0.0379	0.6422	0.7492	0.056*

	U11	U22	U33	U12	U13	U23
Hg1	0.0544 (2)	0.04113 (17)	0.0603 (2)	0.00092 (15)	0.00422 (17)	−0.00082 (14)
I1	0.0978 (6)	0.0521 (4)	0.1078 (7)	0.0131 (4)	−0.0354 (5)	0.0050 (4)
I2	0.0660 (4)	0.0555 (4)	0.0845 (5)	0.0031 (3)	−0.0154 (4)	−0.0110 (3)
N1	0.039 (3)	0.044 (3)	0.037 (3)	0.001 (3)	0.003 (3)	−0.002 (3)
N2	0.035 (3)	0.039 (3)	0.041 (3)	0.002 (3)	0.000 (3)	0.001 (3)
C1	0.040 (4)	0.053 (5)	0.046 (4)	−0.002 (4)	0.009 (3)	−0.006 (4)
C2	0.041 (4)	0.072 (6)	0.035 (4)	0.012 (4)	0.000 (3)	−0.002 (4)
C3	0.061 (6)	0.098 (9)	0.073 (7)	0.016 (6)	0.029 (6)	−0.004 (6)
C4	0.070 (7)	0.058 (6)	0.062 (6)	0.019 (5)	0.001 (5)	−0.020 (5)
C5	0.058 (5)	0.045 (4)	0.056 (5)	0.003 (4)	0.004 (4)	−0.002 (4)
C6	0.038 (4)	0.038 (4)	0.040 (4)	0.001 (3)	−0.004 (3)	−0.002 (3)
C7	0.039 (4)	0.040 (4)	0.035 (4)	0.003 (3)	−0.009 (3)	−0.001 (3)
C8	0.057 (5)	0.047 (5)	0.058 (5)	−0.009 (4)	−0.004 (4)	−0.002 (4)
C9	0.051 (5)	0.051 (5)	0.062 (6)	−0.016 (4)	0.003 (4)	0.007 (4)
C10	0.038 (4)	0.057 (5)	0.048 (5)	−0.001 (4)	−0.005 (3)	0.010 (4)
C11	0.059 (6)	0.080 (7)	0.067 (6)	−0.001 (5)	0.031 (5)	0.000 (5)
C12	0.042 (4)	0.048 (4)	0.050 (5)	0.003 (4)	0.009 (4)	−0.003 (4)

Hg1—I1	2.6587 (9)	C6—N1	1.325 (10)
Hg1—I2	2.6684 (8)	C6—C7	1.496 (11)
Hg1—N1	2.377 (7)	C7—N2	1.335 (10)
Hg1—N2	2.389 (6)	C7—C8	1.382 (12)
C1—N1	1.335 (10)	C8—C9	1.384 (14)
C1—C2	1.380 (13)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.373 (13)
C2—C4	1.390 (15)	C9—H9	0.9300
C2—C3	1.521 (13)	C10—C12	1.382 (12)
C3—H3A	0.9600	C10—C11	1.505 (13)
C3—H3B	0.9600	C11—H11A	0.9600
C3—H3C	0.9600	C11—H11B	0.9600
C4—C5	1.368 (14)	C11—H11C	0.9600
C4—H4	0.9300	C12—N2	1.339 (10)
C5—C6	1.392 (11)	C12—H12	0.9300
C5—H5	0.9300
I1—Hg1—I2	129.89 (3)	C4—C5—C6	119.1 (9)
N1—Hg1—I1	113.59 (16)	C4—C5—H5	120.5
N1—Hg1—N2	69.7 (2)	C6—C5—H5	120.5
N1—Hg1—I2	106.53 (16)	N1—C6—C5	120.9 (8)
N2—Hg1—I1	107.15 (15)	N1—C6—C7	117.6 (7)
N2—Hg1—I2	114.22 (15)	C5—C6—C7	121.5 (7)
C1—N1—Hg1	122.0 (6)	N2—C7—C8	121.1 (8)
C6—N1—Hg1	117.9 (5)	N2—C7—C6	117.4 (7)
C6—N1—C1	119.9 (7)	C8—C7—C6	121.5 (7)
C7—N2—Hg1	117.3 (5)	C7—C8—C9	118.7 (9)
C7—N2—C12	119.4 (7)	C7—C8—H8	120.7
C12—N2—Hg1	123.3 (5)	C9—C8—H8	120.7
N1—C1—C2	122.9 (9)	C10—C9—C8	120.8 (8)
N1—C1—H1	118.5	C10—C9—H9	119.6
C2—C1—H1	118.5	C8—C9—H9	119.6
C1—C2—C4	116.9 (8)	C9—C10—C12	116.8 (8)
C1—C2—C3	119.9 (10)	C9—C10—C11	122.3 (9)
C4—C2—C3	123.2 (9)	C12—C10—C11	120.9 (9)
C2—C3—H3A	109.5	C10—C11—H11A	109.5
C2—C3—H3B	109.5	C10—C11—H11B	109.5
H3A—C3—H3B	109.5	H11A—C11—H11B	109.5
C2—C3—H3C	109.5	C10—C11—H11C	109.5
H3A—C3—H3C	109.5	H11A—C11—H11C	109.5
H3B—C3—H3C	109.5	H11B—C11—H11C	109.5
C5—C4—C2	120.3 (9)	N2—C12—C10	123.2 (8)
C5—C4—H4	119.8	N2—C12—H12	118.4
C2—C4—H4	119.8	C10—C12—H12	118.4
I1—Hg1—N1—C1	82.9 (6)	C5—C6—N1—C1	−2.1 (12)
I1—Hg1—N1—C6	−101.5 (5)	C7—C6—N1—C1	178.3 (7)
I2—Hg1—N1—C1	−66.4 (6)	C5—C6—N1—Hg1	−177.8 (6)
I2—Hg1—N1—C6	109.2 (5)	C7—C6—N1—Hg1	2.6 (9)
N2—Hg1—N1—C1	−176.7 (7)	N1—C6—C7—N2	−3.3 (11)
N2—Hg1—N1—C6	−1.1 (5)	C5—C6—C7—N2	177.1 (8)
I1—Hg1—N2—C7	108.7 (5)	N1—C6—C7—C8	178.0 (8)
I1—Hg1—N2—C12	−71.7 (6)	C5—C6—C7—C8	−1.6 (12)
I2—Hg1—N2—C7	−100.3 (5)	C8—C7—N2—C12	1.4 (12)
I2—Hg1—N2—C12	79.3 (6)	C6—C7—N2—C12	−177.3 (7)
N1—Hg1—N2—C7	−0.8 (5)	C8—C7—N2—Hg1	−179.0 (6)
N1—Hg1—N2—C12	178.9 (7)	C6—C7—N2—Hg1	2.3 (9)
C2—C1—N1—C6	1.5 (13)	N2—C7—C8—C9	−1.9 (13)
C2—C1—N1—Hg1	177.0 (6)	C6—C7—C8—C9	176.7 (8)
N1—C1—C2—C4	−1.1 (13)	C7—C8—C9—C10	0.6 (15)
N1—C1—C2—C3	−178.3 (9)	C8—C9—C10—C12	1.2 (14)
C1—C2—C4—C5	1.4 (14)	C8—C9—C10—C11	−177.2 (9)
C3—C2—C4—C5	178.5 (10)	C9—C10—C12—N2	−1.8 (13)
C2—C4—C5—C6	−2.1 (15)	C11—C10—C12—N2	176.6 (9)
C4—C5—C6—N1	2.5 (14)	C10—C12—N2—C7	0.6 (13)
C4—C5—C6—C7	−178.0 (8)	C10—C12—N2—Hg1	−179.1 (6)

Hg1—I1	2.6587 (9)
Hg1—I2	2.6684 (8)
Hg1—N1	2.377 (7)
Hg1—N2	2.389 (6)

I1—Hg1—I2	129.89 (3)
N1—Hg1—I1	113.59 (16)
N1—Hg1—N2	69.7 (2)
N1—Hg1—I2	106.53 (16)
N2—Hg1—I1	107.15 (15)
N2—Hg1—I2	114.22 (15)