(6,6'-Dimethyl-2,2'-bipyridine-κN,N')diiodidomercury(II).

In the title complex, [HgI(2)(C(12)H(12)N(2))], the Hg(II) atom has a distorted tetra-hedral coordination formed by two N atoms of the 6,6'-dimethyl-2,2'-bipyridine ligand and two terminal I atoms [N-Hg-N = 70.1 (2) and I-Hg-I = 130.59 (3)°]. The crystal packing features π-π contacts between the pyridine rings of adjacent mol-ecules [centroid-centroid distance = 3.773 (5) Å] and also between a pyridine ring of one mol-ecule and the five-membered chelate ring of an adjacent mol-ecule [centroid-centroid distance = 3.668 (4) Å].

Related literature

For the structures of metal complexes with a 6,6′-dimethyl-2,2′-bipyridine ligand, see: Akbarzadeh Torbati et al. (2010 ▶); Alizadeh et al. (2010 ▶); Alizadeh, Kalateh, Ebadi et al. (2009 ▶); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ▶); Alizadeh, Khoshtarkib et al. (2009 ▶); Itoh et al. (2005 ▶); Kou et al. (2008 ▶); Onggo et al. (2005 ▶).

Experimental

Crystal data

[HgI2(C12H12N2)]

M = 638.63

Monoclinic,

a = 8.8096 (18) Å

b = 12.025 (2) Å

c = 14.693 (3) Å

β = 101.88 (3)°

V = 1523.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 14.14 mm−1

T = 298 K

0.16 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.128, T max = 0.186

9361 measured reflections

4057 independent reflections

3409 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.095

S = 1.10

4057 reflections

154 parameters

H-atom parameters constrained

Δρmax = 1.22 e Å−3

Δρmin = −1.23 e Å−3

Data collection: APEX2 (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: 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/S1600536811004041/ya2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004041/ya2136Isup2.hkl

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

[HgI2(C12H12N2)]	F(000) = 1136
Mr = 638.63	Dx = 2.785 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1223 reflections
a = 8.8096 (18) Å	θ = 2.2–29.2°
b = 12.025 (2) Å	µ = 14.14 mm−1
c = 14.693 (3) Å	T = 298 K
β = 101.88 (3)°	Prism, colorless
V = 1523.2 (5) Å3	0.16 × 0.15 × 0.12 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4057 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→12
Tmin = 0.128, Tmax = 0.186	k = −16→13
9361 measured reflections	l = −20→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0397P)2 + 3.5854P] where P = (Fo2 + 2Fc2)/3
4057 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 1.22 e Å−3
0 restraints	Δρmin = −1.23 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
C1	0.6805 (9)	0.4904 (8)	0.1498 (7)	0.065 (2)
H1A	0.6238	0.5560	0.1595	0.077*
H1B	0.7749	0.4868	0.1960	0.077*
H1C	0.6186	0.4258	0.1547	0.077*
C2	0.7174 (7)	0.4943 (6)	0.0569 (5)	0.0493 (16)
C3	0.6678 (9)	0.4111 (7)	−0.0091 (6)	0.061 (2)
H3	0.6079	0.3520	0.0042	0.073*
C4	0.7097 (10)	0.4188 (7)	−0.0941 (7)	0.069 (2)
H4	0.6773	0.3644	−0.1388	0.083*
C5	0.7983 (9)	0.5055 (7)	−0.1137 (6)	0.060 (2)
H5	0.8272	0.5100	−0.1710	0.072*
C6	0.8444 (7)	0.5869 (6)	−0.0461 (5)	0.0478 (15)
C7	0.9441 (7)	0.6807 (6)	−0.0608 (4)	0.0445 (14)
C8	0.9964 (10)	0.6955 (9)	−0.1438 (6)	0.066 (2)
H8	0.9628	0.6477	−0.1936	0.079*
C9	1.0961 (13)	0.7794 (10)	−0.1518 (8)	0.080 (3)
H9	1.1294	0.7900	−0.2073	0.096*
C10	1.1474 (10)	0.8489 (8)	−0.0772 (8)	0.074 (3)
H10	1.2190	0.9046	−0.0812	0.089*
C11	1.0915 (9)	0.8353 (7)	0.0045 (7)	0.0592 (19)
C12	1.1391 (11)	0.9092 (8)	0.0862 (8)	0.079 (3)
H12A	1.1882	0.8659	0.1389	0.094*
H12B	1.0493	0.9456	0.0998	0.094*
H12C	1.2106	0.9640	0.0728	0.094*
N1	0.8032 (6)	0.5792 (4)	0.0366 (4)	0.0399 (11)
N2	0.9903 (6)	0.7526 (5)	0.0104 (4)	0.0452 (12)
I1	1.05284 (6)	0.68838 (5)	0.30203 (4)	0.06506 (16)
I2	0.61128 (6)	0.85868 (4)	0.09788 (4)	0.05659 (14)
Hg1	0.86805 (3)	0.73253 (2)	0.139654 (19)	0.04718 (9)

	U11	U22	U33	U12	U13	U23
C1	0.051 (4)	0.060 (5)	0.081 (6)	−0.010 (3)	0.009 (4)	0.019 (4)
C2	0.041 (3)	0.037 (3)	0.066 (4)	0.003 (2)	0.003 (3)	0.005 (3)
C3	0.047 (3)	0.045 (4)	0.082 (6)	0.004 (3)	−0.005 (4)	−0.010 (4)
C4	0.062 (4)	0.056 (5)	0.077 (6)	0.008 (4)	−0.012 (4)	−0.027 (4)
C5	0.057 (4)	0.068 (5)	0.051 (4)	0.014 (4)	0.004 (3)	−0.018 (4)
C6	0.041 (3)	0.058 (4)	0.042 (3)	0.019 (3)	0.002 (2)	−0.005 (3)
C7	0.045 (3)	0.051 (4)	0.039 (3)	0.014 (3)	0.012 (2)	0.006 (3)
C8	0.066 (5)	0.088 (6)	0.047 (4)	0.020 (4)	0.020 (4)	0.009 (4)
C9	0.087 (6)	0.094 (8)	0.070 (6)	0.019 (6)	0.041 (5)	0.034 (6)
C10	0.062 (5)	0.065 (6)	0.107 (8)	0.009 (4)	0.046 (5)	0.028 (5)
C11	0.050 (4)	0.045 (4)	0.088 (6)	0.003 (3)	0.026 (4)	0.017 (4)
C12	0.074 (6)	0.053 (5)	0.116 (8)	−0.016 (4)	0.034 (6)	−0.012 (5)
N1	0.038 (2)	0.036 (3)	0.045 (3)	0.005 (2)	0.006 (2)	−0.002 (2)
N2	0.045 (3)	0.040 (3)	0.054 (3)	0.006 (2)	0.021 (2)	0.006 (2)
I1	0.0656 (3)	0.0743 (4)	0.0493 (3)	0.0076 (3)	−0.0020 (2)	−0.0064 (2)
I2	0.0534 (2)	0.0536 (3)	0.0609 (3)	0.0024 (2)	0.0073 (2)	−0.0054 (2)
Hg1	0.05023 (14)	0.04953 (15)	0.04286 (13)	−0.00229 (11)	0.01209 (10)	−0.00399 (11)

C1—C2	1.468 (12)	C8—C9	1.359 (15)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.379 (16)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.340 (9)	C10—C11	1.398 (13)
C2—C3	1.399 (10)	C10—H10	0.9300
C3—C4	1.377 (14)	C11—N2	1.351 (9)
C3—H3	0.9300	C11—C12	1.483 (14)
C4—C5	1.367 (13)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.394 (10)	C12—H12C	0.9600
C5—H5	0.9300	N1—Hg1	2.380 (5)
C6—N1	1.341 (9)	N2—Hg1	2.381 (6)
C6—C7	1.473 (11)	I1—Hg1	2.6503 (10)
C7—N2	1.354 (9)	I2—Hg1	2.6876 (7)
C7—C8	1.401 (10)
C2—C1—H1A	109.5	C8—C9—C10	119.5 (9)
C2—C1—H1B	109.5	C8—C9—H9	120.2
H1A—C1—H1B	109.5	C10—C9—H9	120.2
C2—C1—H1C	109.5	C9—C10—C11	119.8 (9)
H1A—C1—H1C	109.5	C9—C10—H10	120.1
H1B—C1—H1C	109.5	C11—C10—H10	120.1
N1—C2—C3	120.0 (8)	N2—C11—C10	119.7 (9)
N1—C2—C1	118.4 (7)	N2—C11—C12	118.1 (8)
C3—C2—C1	121.6 (7)	C10—C11—C12	122.3 (8)
C4—C3—C2	118.5 (8)	C11—C12—H12A	109.5
C4—C3—H3	120.8	C11—C12—H12B	109.5
C2—C3—H3	120.8	H12A—C12—H12B	109.5
C5—C4—C3	120.9 (8)	C11—C12—H12C	109.5
C5—C4—H4	119.5	H12A—C12—H12C	109.5
C3—C4—H4	119.5	H12B—C12—H12C	109.5
C4—C5—C6	118.7 (8)	C2—N1—C6	121.6 (6)
C4—C5—H5	120.6	C2—N1—Hg1	121.4 (5)
C6—C5—H5	120.6	C6—N1—Hg1	116.7 (5)
N1—C6—C5	120.2 (8)	C11—N2—C7	121.2 (7)
N1—C6—C7	117.8 (6)	C11—N2—Hg1	122.6 (6)
C5—C6—C7	121.9 (7)	C7—N2—Hg1	116.0 (4)
N2—C7—C8	119.4 (7)	N1—Hg1—N2	70.1 (2)
N2—C7—C6	118.0 (6)	N1—Hg1—I1	116.12 (12)
C8—C7—C6	122.6 (7)	N2—Hg1—I1	116.33 (14)
C9—C8—C7	120.3 (9)	N1—Hg1—I2	102.20 (12)
C9—C8—H8	119.8	N2—Hg1—I2	104.98 (13)
C7—C8—H8	119.8	I1—Hg1—I2	130.59 (3)
N1—C2—C3—C4	0.3 (10)	C5—C6—N1—Hg1	−174.1 (5)
C1—C2—C3—C4	−178.5 (7)	C7—C6—N1—Hg1	8.4 (7)
C2—C3—C4—C5	0.2 (12)	C10—C11—N2—C7	1.4 (11)
C3—C4—C5—C6	−0.7 (12)	C12—C11—N2—C7	−178.7 (7)
C4—C5—C6—N1	0.6 (10)	C10—C11—N2—Hg1	−173.7 (6)
C4—C5—C6—C7	177.9 (6)	C12—C11—N2—Hg1	6.2 (10)
N1—C6—C7—N2	1.0 (8)	C8—C7—N2—C11	−3.1 (10)
C5—C6—C7—N2	−176.4 (6)	C6—C7—N2—C11	174.8 (6)
N1—C6—C7—C8	178.7 (6)	C8—C7—N2—Hg1	172.3 (5)
C5—C6—C7—C8	1.3 (10)	C6—C7—N2—Hg1	−9.8 (7)
N2—C7—C8—C9	1.8 (11)	C2—N1—Hg1—N2	176.3 (5)
C6—C7—C8—C9	−175.9 (8)	C6—N1—Hg1—N2	−9.7 (4)
C7—C8—C9—C10	1.1 (14)	C2—N1—Hg1—I1	65.9 (5)
C8—C9—C10—C11	−2.7 (15)	C6—N1—Hg1—I1	−120.0 (4)
C9—C10—C11—N2	1.5 (13)	C2—N1—Hg1—I2	−82.0 (4)
C9—C10—C11—C12	−178.4 (9)	C6—N1—Hg1—I2	92.1 (4)
C3—C2—N1—C6	−0.4 (9)	C11—N2—Hg1—N1	−174.6 (6)
C1—C2—N1—C6	178.5 (6)	C7—N2—Hg1—N1	10.1 (4)
C3—C2—N1—Hg1	173.4 (5)	C11—N2—Hg1—I1	−64.5 (6)
C1—C2—N1—Hg1	−7.8 (8)	C7—N2—Hg1—I1	120.2 (4)
C5—C6—N1—C2	−0.1 (9)	C11—N2—Hg1—I2	87.6 (5)
C7—C6—N1—C2	−177.5 (5)	C7—N2—Hg1—I2	−87.7 (4)

Table 1

Selected bond lengths (Å)

N1—Hg1	2.380 (5)
N2—Hg1	2.381 (6)
I1—Hg1	2.6503 (10)
I2—Hg1	2.6876 (7)