Di-μ-chlorido-bis-[(2-amino-4-methyl-pyridine-κN)-chloridomercury(II)].

In the centrosymmetric dinuclear title compound, [Hg(2)Cl(4)(C(6)H(8)N(2))(2)], the Hg(II) ion is four-coordinated by one pyridine N atom from a 2-amino-4-methyl-pyridine ligand, one terminal Cl atom and two bridging Cl atoms. A distorted tetra-hedral geometry is formed around each Hg(II) ion. The crystal packing is stabilized by intra- and inter-molecular N-H⋯Cl hydrogen bonding. There are also π-π stacking inter-actions in the structure, with centroid-to-centroid distances of 3.594 (6) Å.

Related literature

For a coordination compound of 2-amino-4-methyl­pyridine, see: Arab Ahmadi et al. (2011 ▶). For proton-transfer compounds of 2-amino-4-methyl­pyridine, see: Gharbia et al. (2008 ▶); Choudhury et al. (2009 ▶); Das et al. (2010 ▶); Hemamalini & Fun (2010 ▶); Aghabozorg et al. (2011 ▶); Eshtiagh-Hosseini et al. (2010 ▶). For mixed-ligand complexes of 2-amino-4-methyl­pyridine, see: Zhang et al. (2008 ▶); Castillo et al. (2001 ▶); Yenikaya et al. (2011 ▶). For similar structures, see: Baul et al. (2004 ▶).

Experimental

Crystal data

[Hg2Cl4(C6H8N2)2]

M = 759.27

Monoclinic,

a = 7.1777 (14) Å

b = 9.1672 (18) Å

c = 14.546 (3) Å

β = 101.92 (3)°

V = 936.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 16.94 mm−1

T = 120 K

0.25 × 0.25 × 0.20 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (shape of crystal determined optically; X-RED and X-SHAPE, Stoe & Cie, 2005 ▶) T min = 0.101, T max = 0.133

6495 measured reflections

2507 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.111

S = 1.00

2507 reflections

109 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.35 e Å−3

Δρmin = −2.80 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039803/bt6826sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039803/bt6826Isup2.hkl

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

C12H16Cl4Hg2N4	F(000) = 688
Mr = 759.27	Dx = 2.693 Mg m−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 2507 reflections
a = 7.1777 (14) Å	θ = 2.6–29.1°
b = 9.1672 (18) Å	µ = 16.94 mm−1
c = 14.546 (3) Å	T = 120 K
β = 101.92 (3)°	Block, colorless
V = 936.5 (3) Å3	0.25 × 0.25 × 0.20 mm
Z = 2

Stoe IPDS 2T diffractometer	2507 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.1°, θmin = 2.6°
rotation method scans	h = −9→9
Absorption correction: numerical shape of crystal determined optically	k = −12→10
Tmin = 0.101, Tmax = 0.133	l = −19→19
6495 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0604P)2] where P = (Fo2 + 2Fc2)/3
2507 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 2.35 e Å−3
2 restraints	Δρmin = −2.80 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	0.21238 (5)	0.47797 (4)	0.94011 (2)	0.02164 (12)
Cl1	0.3952 (3)	0.6882 (3)	0.98493 (15)	0.0237 (4)
Cl2	0.1382 (3)	0.3856 (2)	1.10331 (13)	0.0205 (4)
N1	0.1135 (11)	0.2841 (9)	0.8633 (5)	0.0210 (15)
N2	0.0000 (13)	0.4145 (10)	0.7272 (5)	0.0278 (18)
C1	0.0312 (12)	0.2842 (11)	0.7714 (6)	0.0221 (18)
C2	−0.0152 (13)	0.1524 (12)	0.7224 (6)	0.025 (2)
H2	−0.0709	0.1541	0.6572	0.030*
C3	0.0199 (16)	0.0208 (12)	0.7685 (7)	0.031 (2)
C4	−0.022 (2)	−0.1198 (14)	0.7162 (8)	0.046 (3)
H4A	−0.1242	−0.1048	0.6610	0.068*
H4B	−0.0612	−0.1931	0.7573	0.068*
H4C	0.0930	−0.1536	0.6959	0.068*
C5	0.0993 (15)	0.0221 (12)	0.8661 (7)	0.028 (2)
H5	0.1206	−0.0662	0.9009	0.034*
C6	0.1444 (14)	0.1542 (11)	0.9089 (6)	0.0241 (18)
H6	0.2003	0.1550	0.9741	0.029*
H2A	−0.080 (14)	0.429 (19)	0.675 (5)	0.06 (4)*
H2B	−0.028 (19)	0.495 (7)	0.753 (9)	0.03 (3)*

	U11	U22	U33	U12	U13	U23
Hg1	0.02222 (18)	0.0215 (2)	0.01994 (17)	−0.00052 (14)	0.00134 (11)	−0.00125 (13)
Cl1	0.0237 (10)	0.0218 (12)	0.0245 (10)	−0.0020 (8)	0.0025 (8)	0.0015 (8)
Cl2	0.0194 (9)	0.0248 (11)	0.0177 (8)	0.0030 (8)	0.0047 (7)	0.0008 (7)
N1	0.021 (4)	0.020 (4)	0.022 (3)	−0.003 (3)	0.005 (3)	−0.001 (3)
N2	0.040 (5)	0.026 (5)	0.016 (3)	0.010 (4)	0.001 (3)	−0.001 (3)
C1	0.010 (4)	0.033 (5)	0.024 (4)	0.001 (3)	0.005 (3)	0.003 (3)
C2	0.020 (4)	0.038 (6)	0.017 (4)	−0.004 (4)	0.006 (3)	−0.010 (4)
C3	0.038 (6)	0.033 (6)	0.026 (4)	−0.015 (4)	0.017 (4)	−0.012 (4)
C4	0.073 (9)	0.036 (7)	0.033 (5)	−0.030 (6)	0.023 (6)	−0.022 (5)
C5	0.033 (5)	0.023 (5)	0.031 (5)	0.003 (4)	0.014 (4)	0.002 (4)
C6	0.025 (5)	0.026 (5)	0.019 (4)	0.001 (4)	0.002 (3)	0.002 (3)

Hg1—N1	2.141 (8)	C2—C3	1.377 (16)
Hg1—Cl1	2.347 (2)	C2—H2	0.9500
Hg1—Cl2	2.6755 (19)	C3—C5	1.417 (16)
Hg1—Cl2i	2.763 (2)	C3—C4	1.496 (14)
Cl2—Hg1i	2.763 (2)	C4—H4A	0.9800
N1—C1	1.345 (12)	C4—H4B	0.9800
N1—C6	1.359 (13)	C4—H4C	0.9800
N2—C1	1.353 (13)	C5—C6	1.369 (15)
N2—H2A	0.87 (2)	C5—H5	0.9500
N2—H2B	0.87 (2)	C6—H6	0.9500
C1—C2	1.407 (14)
N1—Hg1—Cl1	158.87 (19)	C3—C2—H2	119.8
N1—Hg1—Cl2	95.45 (19)	C1—C2—H2	119.8
Cl1—Hg1—Cl2	102.46 (7)	C2—C3—C5	118.4 (9)
N1—Hg1—Cl2i	93.9 (2)	C2—C3—C4	120.6 (10)
Cl1—Hg1—Cl2i	97.04 (8)	C5—C3—C4	120.9 (11)
Cl2—Hg1—Cl2i	90.41 (7)	C3—C4—H4A	109.5
Hg1—Cl2—Hg1i	89.59 (7)	C3—C4—H4B	109.5
C1—N1—C6	118.7 (9)	H4A—C4—H4B	109.5
C1—N1—Hg1	123.2 (7)	C3—C4—H4C	109.5
C6—N1—Hg1	118.0 (6)	H4A—C4—H4C	109.5
C1—N2—H2A	125 (10)	H4B—C4—H4C	109.5
C1—N2—H2B	125 (9)	C6—C5—C3	118.1 (10)
H2A—N2—H2B	94 (10)	C6—C5—H5	121.0
N1—C1—N2	117.9 (9)	C3—C5—H5	121.0
N1—C1—C2	120.8 (9)	N1—C6—C5	123.6 (9)
N2—C1—C2	121.3 (8)	N1—C6—H6	118.2
C3—C2—C1	120.3 (8)	C5—C6—H6	118.2
N1—Hg1—Cl2—Hg1i	−94.0 (2)	C6—N1—C1—C2	−2.5 (12)
Cl1—Hg1—Cl2—Hg1i	97.30 (8)	Hg1—N1—C1—C2	174.1 (6)
Cl2i—Hg1—Cl2—Hg1i	0.0	N1—C1—C2—C3	1.2 (12)
Cl1—Hg1—N1—C1	−64.4 (10)	N2—C1—C2—C3	179.2 (9)
Cl2—Hg1—N1—C1	147.6 (6)	C1—C2—C3—C5	1.4 (14)
Cl2i—Hg1—N1—C1	56.8 (6)	C1—C2—C3—C4	−177.6 (9)
Cl1—Hg1—N1—C6	112.2 (7)	C2—C3—C5—C6	−2.6 (15)
Cl2—Hg1—N1—C6	−35.8 (6)	C4—C3—C5—C6	176.3 (9)
Cl2i—Hg1—N1—C6	−126.6 (6)	C1—N1—C6—C5	1.2 (13)
C6—N1—C1—N2	179.4 (8)	Hg1—N1—C6—C5	−175.6 (7)
Hg1—N1—C1—N2	−4.0 (11)	C3—C5—C6—N1	1.4 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl2i	0.87 (2)	2.62 (7)	3.380 (8)	146 (11)
N2—H2A···Cl2ii	0.87 (2)	2.68 (11)	3.379 (9)	139 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl2i	0.87 (2)	2.62 (7)	3.380 (8)	146 (11)
N2—H2A⋯Cl2ii	0.87 (2)	2.68 (11)	3.379 (9)	139 (13)

Symmetry codes: (i) ; (ii) .