Bis(2-amino-3-methyl-pyridine-κN(1))dichloridomercury(II).

In the title compound, [HgCl(2)(C(6)H(8)N(2))(2)], the two independent Hg(II) cations are each located on a twofold rotation axis and coordinated by two pyridine N atoms from two 2-amino-3-methyl-pyridine ligands and two Cl(-) anions in a distorted tetra-hedral geometry. An intra-molecular N-H⋯Cl hydrogen bond occurs in each independent complex mol-ecule. Inter-molecular N-H⋯Cl hydrogen bonds occur in the crystal structure.

Related literature

For coordination modes of 2-amino-3-methyl­pyridine (ampy), see: Arab Ahmadi et al. (2011 ▶); Tadjarodi et al. (2010 ▶); Amani Komaei et al. (1999 ▶); Ziegler et al. (2000 ▶); Castillo et al. (2001 ▶); Chen et al. (2005 ▶). For proton-transfer compounds incorporating ampy, see: Carnevale et al. (2010 ▶).

Experimental

Crystal data

[HgCl2(C6H8N2)2]

M = 487.78

Monoclinic,

a = 16.495 (3) Å

b = 6.6320 (13) Å

c = 16.273 (3) Å

β = 119.56 (3)°

V = 1548.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 10.28 mm−1

T = 298 K

0.30 × 0.30 × 0.27 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶)] T min = 0.149, T max = 0.168

5454 measured reflections

2912 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 1.03

2912 reflections

188 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.40 e Å−3

Δρmin = −2.67 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); 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/S1600536812032126/xu5594sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032126/xu5594Isup2.hkl

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

[HgCl2(C6H8N2)2]	F(000) = 920
Mr = 487.78	Dx = 2.092 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2912 reflections
a = 16.495 (3) Å	θ = 2.5–26.0°
b = 6.6320 (13) Å	µ = 10.28 mm−1
c = 16.273 (3) Å	T = 298 K
β = 119.56 (3)°	Block, colorless
V = 1548.5 (7) Å3	0.30 × 0.30 × 0.27 mm
Z = 4

Stoe IPDS 2T diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
rotation method scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie, 2005)]	h = −16→20
Tmin = 0.149, Tmax = 0.168	k = −7→8
5454 measured reflections	l = −19→20

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2912 reflections	Δρmax = 2.40 e Å−3
188 parameters	Δρmin = −2.67 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (5)

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	0.0000	0.19701 (7)	0.2500	0.04474 (19)
Hg2	0.5000	0.76184 (6)	0.2500	0.04007 (19)
Cl1	0.13755 (15)	0.0118 (3)	0.36667 (16)	0.0565 (6)
Cl2	0.35836 (16)	0.9352 (4)	0.22391 (16)	0.0590 (6)
N1	0.0500 (5)	0.4038 (9)	0.1715 (4)	0.0407 (15)
N2	0.1527 (6)	0.1618 (12)	0.1736 (6)	0.0497 (17)
N3	0.4556 (4)	0.5485 (9)	0.1232 (4)	0.0359 (14)
N4	0.3477 (6)	0.7778 (10)	0.0184 (5)	0.0472 (19)
C1	0.1163 (5)	0.3496 (11)	0.1495 (5)	0.0362 (16)
C2	0.1430 (6)	0.4814 (13)	0.1001 (5)	0.0441 (19)
C3	0.2151 (7)	0.4171 (18)	0.0751 (8)	0.069 (3)
H3A	0.2217	0.5192	0.0370	0.104*
H3B	0.1962	0.2928	0.0404	0.104*
H3C	0.2737	0.3980	0.1318	0.104*
C4	0.1028 (7)	0.6659 (13)	0.0756 (6)	0.051 (2)
H4	0.1206	0.7549	0.0432	0.061*
C5	0.0361 (7)	0.7229 (12)	0.0981 (6)	0.049 (2)
H5	0.0088	0.8499	0.0813	0.059*
C6	0.0103 (6)	0.5893 (13)	0.1459 (5)	0.0454 (19)
H6	−0.0352	0.6267	0.1609	0.055*
C7	0.3884 (6)	0.5942 (11)	0.0346 (5)	0.0373 (16)
C8	0.3618 (6)	0.4525 (12)	−0.0402 (5)	0.0403 (17)
C9	0.2853 (7)	0.5040 (17)	−0.1374 (6)	0.066 (3)
H9A	0.2783	0.3968	−0.1801	0.100*
H9B	0.3005	0.6267	−0.1581	0.100*
H9C	0.2280	0.5215	−0.1364	0.100*
C10	0.4071 (8)	0.2741 (12)	−0.0193 (6)	0.050 (2)
H10	0.3904	0.1785	−0.0668	0.060*
C11	0.4775 (7)	0.2304 (13)	0.0704 (6)	0.049 (2)
H11	0.5096	0.1087	0.0833	0.058*
C12	0.4993 (6)	0.3695 (12)	0.1401 (5)	0.0405 (17)
H12	0.5458	0.3394	0.2012	0.049*
H2A	0.158 (7)	0.107 (14)	0.224 (4)	0.061*
H4A	0.301 (5)	0.788 (14)	−0.038 (4)	0.061*
H2B	0.202 (4)	0.161 (15)	0.168 (7)	0.061*
H4B	0.348 (7)	0.845 (14)	0.064 (5)	0.061*

	U11	U22	U33	U12	U13	U23
Hg1	0.0379 (3)	0.0561 (3)	0.0446 (3)	0.000	0.0238 (2)	0.000
Hg2	0.0326 (3)	0.0476 (3)	0.0330 (3)	0.000	0.0108 (2)	0.000
Cl1	0.0393 (11)	0.0617 (13)	0.0566 (12)	−0.0032 (9)	0.0147 (10)	0.0151 (9)
Cl2	0.0442 (11)	0.0714 (14)	0.0564 (12)	0.0166 (10)	0.0210 (10)	−0.0068 (10)
N1	0.043 (4)	0.041 (4)	0.036 (3)	0.001 (3)	0.018 (3)	0.001 (2)
N2	0.048 (4)	0.051 (4)	0.063 (5)	0.006 (3)	0.037 (4)	0.001 (3)
N3	0.036 (3)	0.036 (3)	0.034 (3)	0.007 (3)	0.016 (3)	0.001 (2)
N4	0.049 (5)	0.039 (4)	0.040 (4)	0.008 (3)	0.012 (3)	0.003 (3)
C1	0.029 (4)	0.046 (4)	0.033 (3)	−0.007 (3)	0.014 (3)	−0.009 (3)
C2	0.045 (5)	0.054 (5)	0.039 (4)	−0.015 (4)	0.025 (4)	−0.009 (3)
C3	0.055 (6)	0.085 (8)	0.081 (7)	−0.007 (5)	0.044 (6)	0.003 (5)
C4	0.065 (6)	0.043 (4)	0.052 (5)	−0.015 (4)	0.034 (4)	−0.003 (4)
C5	0.058 (6)	0.042 (5)	0.042 (4)	0.002 (4)	0.020 (4)	0.002 (3)
C6	0.040 (4)	0.049 (5)	0.039 (4)	0.009 (4)	0.014 (4)	0.001 (3)
C7	0.045 (4)	0.037 (4)	0.030 (3)	−0.006 (3)	0.018 (3)	−0.001 (3)
C8	0.042 (4)	0.049 (4)	0.031 (4)	0.002 (3)	0.019 (3)	0.002 (3)
C9	0.054 (6)	0.087 (7)	0.029 (4)	0.010 (5)	−0.002 (4)	−0.007 (4)
C10	0.066 (6)	0.050 (5)	0.036 (4)	−0.001 (4)	0.027 (4)	−0.009 (3)
C11	0.058 (6)	0.049 (5)	0.045 (5)	0.012 (4)	0.030 (5)	0.004 (3)
C12	0.042 (4)	0.044 (4)	0.032 (3)	0.005 (3)	0.016 (3)	0.004 (3)

Hg1—N1	2.287 (7)	C2—C3	1.497 (14)
Hg1—N1i	2.287 (7)	C3—H3A	0.9600
Hg1—Cl1i	2.452 (2)	C3—H3B	0.9600
Hg1—Cl1	2.452 (2)	C3—H3C	0.9600
Hg2—N3	2.303 (6)	C4—C5	1.373 (15)
Hg2—N3ii	2.303 (6)	C4—H4	0.9300
Hg2—Cl2ii	2.446 (2)	C5—C6	1.378 (13)
Hg2—Cl2	2.446 (2)	C5—H5	0.9300
N1—C1	1.356 (11)	C6—H6	0.9300
N1—C6	1.360 (10)	C7—C8	1.425 (10)
N2—C1	1.354 (11)	C8—C10	1.351 (12)
N2—H2A	0.86 (2)	C8—C9	1.498 (11)
N2—H2B	0.87 (2)	C9—H9A	0.9600
N3—C12	1.345 (10)	C9—H9B	0.9600
N3—C7	1.350 (9)	C9—H9C	0.9600
N4—C7	1.352 (10)	C10—C11	1.375 (13)
N4—H4A	0.86 (2)	C10—H10	0.9300
N4—H4B	0.87 (2)	C11—C12	1.365 (12)
C1—C2	1.397 (11)	C11—H11	0.9300
C2—C4	1.355 (13)	C12—H12	0.9300
N1—Hg1—N1i	106.3 (3)	C2—C3—H3C	109.5
N1—Hg1—Cl1i	108.60 (16)	H3A—C3—H3C	109.5
N1i—Hg1—Cl1i	106.35 (17)	H3B—C3—H3C	109.5
N1—Hg1—Cl1	106.35 (17)	C2—C4—C5	120.7 (8)
N1i—Hg1—Cl1	108.60 (16)	C2—C4—H4	119.6
Cl1i—Hg1—Cl1	119.88 (11)	C5—C4—H4	119.6
N3—Hg2—N3ii	104.2 (3)	C4—C5—C6	119.0 (8)
N3—Hg2—Cl2ii	107.38 (18)	C4—C5—H5	120.5
N3ii—Hg2—Cl2ii	106.20 (16)	C6—C5—H5	120.5
N3—Hg2—Cl2	106.20 (16)	N1—C6—C5	121.3 (9)
N3ii—Hg2—Cl2	107.38 (18)	N1—C6—H6	119.4
Cl2ii—Hg2—Cl2	123.91 (13)	C5—C6—H6	119.4
C1—N1—C6	119.2 (7)	N3—C7—N4	118.5 (6)
C1—N1—Hg1	123.3 (5)	N3—C7—C8	120.6 (7)
C6—N1—Hg1	117.5 (6)	N4—C7—C8	120.9 (7)
C1—N2—H2A	119 (7)	C10—C8—C7	117.7 (7)
C1—N2—H2B	106 (7)	C10—C8—C9	122.6 (8)
H2A—N2—H2B	116 (10)	C7—C8—C9	119.7 (7)
C12—N3—C7	119.4 (6)	C8—C9—H9A	109.5
C12—N3—Hg2	117.3 (5)	C8—C9—H9B	109.5
C7—N3—Hg2	123.3 (5)	H9A—C9—H9B	109.5
C7—N4—H4A	112 (7)	C8—C9—H9C	109.5
C7—N4—H4B	120 (7)	H9A—C9—H9C	109.5
H4A—N4—H4B	120 (10)	H9B—C9—H9C	109.5
N2—C1—N1	117.8 (7)	C8—C10—C11	121.6 (8)
N2—C1—C2	121.4 (7)	C8—C10—H10	119.2
N1—C1—C2	120.7 (7)	C11—C10—H10	119.2
C4—C2—C1	119.1 (8)	C12—C11—C10	118.6 (8)
C4—C2—C3	121.1 (8)	C12—C11—H11	120.7
C1—C2—C3	119.8 (8)	C10—C11—H11	120.7
C2—C3—H3A	109.5	N3—C12—C11	122.1 (7)
C2—C3—H3B	109.5	N3—C12—H12	118.9
H3A—C3—H3B	109.5	C11—C12—H12	118.9
N1i—Hg1—N1—C1	152.6 (6)	C1—C2—C4—C5	−0.5 (12)
Cl1i—Hg1—N1—C1	−93.3 (5)	C3—C2—C4—C5	179.4 (8)
Cl1—Hg1—N1—C1	37.0 (6)	C2—C4—C5—C6	−0.2 (13)
N1i—Hg1—N1—C6	−27.8 (5)	C1—N1—C6—C5	−0.1 (11)
Cl1i—Hg1—N1—C6	86.3 (5)	Hg1—N1—C6—C5	−179.8 (6)
Cl1—Hg1—N1—C6	−143.4 (5)	C4—C5—C6—N1	0.5 (13)
N3ii—Hg2—N3—C12	−31.0 (5)	C12—N3—C7—N4	−177.6 (8)
Cl2ii—Hg2—N3—C12	81.4 (6)	Hg2—N3—C7—N4	2.9 (10)
Cl2—Hg2—N3—C12	−144.2 (6)	C12—N3—C7—C8	1.8 (12)
N3ii—Hg2—N3—C7	148.5 (7)	Hg2—N3—C7—C8	−177.7 (6)
Cl2ii—Hg2—N3—C7	−99.1 (6)	N3—C7—C8—C10	−1.2 (13)
Cl2—Hg2—N3—C7	35.3 (6)	N4—C7—C8—C10	178.3 (9)
C6—N1—C1—N2	−178.2 (7)	N3—C7—C8—C9	178.3 (8)
Hg1—N1—C1—N2	1.4 (9)	N4—C7—C8—C9	−2.3 (13)
C6—N1—C1—C2	−0.6 (10)	C7—C8—C10—C11	−0.9 (15)
Hg1—N1—C1—C2	179.0 (5)	C9—C8—C10—C11	179.7 (10)
N2—C1—C2—C4	178.4 (8)	C8—C10—C11—C12	2.1 (16)
N1—C1—C2—C4	0.9 (11)	C7—N3—C12—C11	−0.5 (13)
N2—C1—C2—C3	−1.5 (11)	Hg2—N3—C12—C11	179.0 (7)
N1—C1—C2—C3	−179.0 (7)	C10—C11—C12—N3	−1.5 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86 (2)	2.58 (4)	3.420 (9)	164 (10)
N2—H2B···Cl2iii	0.87 (2)	2.72 (7)	3.420 (8)	139 (8)
N4—H4A···Cl1iv	0.86 (2)	2.70 (7)	3.409 (8)	140 (9)
N4—H4B···Cl2	0.87 (2)	2.59 (4)	3.424 (9)	162 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.86 (2)	2.58 (4)	3.420 (9)	164 (10)
N2—H2B⋯Cl2i	0.87 (2)	2.72 (7)	3.420 (8)	139 (8)
N4—H4A⋯Cl1ii	0.86 (2)	2.70 (7)	3.409 (8)	140 (9)
N4—H4B⋯Cl2	0.87 (2)	2.59 (4)	3.424 (9)	162 (9)

Symmetry codes: (i) ; (ii) .