Dichlorido(di-2-pyridylamine)mercury(II).

In the mol-ecule of the title compound, [HgCl(2)(C(10)H(9)N(3))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from the chelating di-2-pyridylamine ligand and by two Cl atoms. In the crystal structure, inter-molecular N-H⋯Cl hydrogen bonds link the mol-ecules into centrosymmetric dimers. There is a π-π contact between the pyridine rings [centroid-centroid distance = 3.896 (5) Å].

Related literature

For related literature, see: Ahmadi et al. (2008 ▶); Kalateh, Ebadi et al. (2008 ▶); Kalateh, Norouzi et al. (2008 ▶); Khavasi et al. (2008 ▶); Tadayon Pour et al. (2008 ▶); Yousefi, Rashidi Vahid et al. (2008 ▶); Yousefi, Tadayon Pour et al. (2008 ▶). For related structures, see: Chen et al. (2006 ▶); Liu et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[HgCl2(C10H9N3)]

M = 442.69

Triclinic,

a = 8.0268 (12) Å

b = 8.6127 (11) Å

c = 9.6118 (14) Å

α = 110.606 (11)°

β = 98.958 (12)°

γ = 96.862 (11)°

V = 603.38 (15) Å3

Z = 2

Mo Kα radiation

μ = 13.17 mm−1

T = 298 (2) K

0.24 × 0.21 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi scan (SADABS; Sheldrick, 1998 ▶) T min = 0.061, T max = 0.142

7105 measured reflections

3214 independent reflections

2806 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.05

3214 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.43 e Å−3

Δρmin = −2.08 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/S1600536808040294/hk2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040294/hk2588Isup2.hkl

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

[HgCl2(C10H9N3)]	Z = 2
Mr = 442.69	F(000) = 408
Triclinic, P1	Dx = 2.437 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0268 (12) Å	Cell parameters from 1652 reflections
b = 8.6127 (11) Å	θ = 2.6–29.2°
c = 9.6118 (14) Å	µ = 13.17 mm−1
α = 110.606 (11)°	T = 298 K
β = 98.958 (12)°	Block, colorless
γ = 96.862 (11)°	0.24 × 0.21 × 0.15 mm
V = 603.38 (15) Å3

Bruker SMART CCD area-detector diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	2806 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 29.2°, θmin = 2.6°
Absorption correction: multi scan (SADABS; Sheldrick, 1998)	h = −10→10
Tmin = 0.061, Tmax = 0.142	k = −11→11
7105 measured reflections	l = −13→12

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.075P)2 + 0.8992P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.026
3214 reflections	Δρmax = 2.43 e Å−3
150 parameters	Δρmin = −2.08 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (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	0.21151 (4)	0.24646 (4)	0.63832 (4)	0.06055 (18)
Cl1	0.4456 (3)	0.1830 (3)	0.7818 (3)	0.0683 (5)
Cl2	−0.0856 (2)	0.1450 (2)	0.6448 (2)	0.0553 (4)
N1	0.1944 (8)	0.5364 (8)	0.7382 (7)	0.0497 (12)
N2	0.2047 (8)	0.5833 (7)	0.5110 (6)	0.0459 (11)
N3	0.2876 (7)	0.3143 (7)	0.4439 (7)	0.0447 (11)
C1	0.1758 (12)	0.5982 (12)	0.8836 (9)	0.0636 (19)
H1	0.1862	0.5294	0.9393	0.076*
C2	0.1428 (12)	0.7553 (13)	0.9537 (9)	0.069 (2)
H2	0.1285	0.7920	1.0537	0.083*
H2B	0.186 (18)	0.662 (18)	0.464 (16)	0.10 (4)*
C3	0.1312 (11)	0.8591 (11)	0.8713 (9)	0.0624 (18)
H3	0.1115	0.9683	0.9157	0.075*
C4	0.1493 (9)	0.7975 (9)	0.7231 (8)	0.0514 (14)
H4	0.1379	0.8635	0.6649	0.062*
C5	0.1848 (7)	0.6352 (7)	0.6597 (7)	0.0398 (11)
C6	0.2674 (7)	0.4531 (7)	0.4151 (7)	0.0395 (10)
C7	0.3045 (9)	0.4711 (10)	0.2836 (7)	0.0499 (13)
H7	0.2849	0.5656	0.2627	0.060*
C8	0.3715 (12)	0.3449 (13)	0.1842 (10)	0.067 (2)
H8	0.4006	0.3559	0.0977	0.080*
C9	0.3935 (9)	0.2066 (10)	0.2156 (9)	0.0587 (18)
H9	0.4365	0.1208	0.1498	0.070*
C10	0.3524 (9)	0.1931 (9)	0.3444 (10)	0.0556 (16)
H10	0.3694	0.0976	0.3648	0.067*

	U11	U22	U33	U12	U13	U23
Hg1	0.0618 (2)	0.0660 (2)	0.0781 (3)	0.02555 (14)	0.02487 (14)	0.04774 (18)
Cl1	0.0653 (11)	0.0710 (11)	0.0816 (13)	0.0210 (9)	0.0091 (9)	0.0445 (10)
Cl2	0.0623 (9)	0.0551 (8)	0.0628 (9)	0.0170 (7)	0.0277 (7)	0.0314 (7)
N1	0.051 (3)	0.058 (3)	0.050 (3)	0.019 (2)	0.014 (2)	0.027 (2)
N2	0.059 (3)	0.043 (2)	0.045 (3)	0.016 (2)	0.015 (2)	0.024 (2)
N3	0.043 (2)	0.041 (2)	0.056 (3)	0.006 (2)	0.013 (2)	0.023 (2)
C1	0.072 (5)	0.078 (5)	0.051 (4)	0.020 (4)	0.017 (3)	0.033 (4)
C2	0.071 (5)	0.084 (6)	0.047 (4)	0.019 (4)	0.012 (3)	0.017 (4)
C3	0.066 (4)	0.061 (4)	0.052 (4)	0.013 (4)	0.015 (3)	0.009 (3)
C4	0.053 (3)	0.045 (3)	0.052 (3)	0.007 (3)	0.008 (3)	0.014 (3)
C5	0.035 (2)	0.043 (3)	0.043 (3)	0.006 (2)	0.007 (2)	0.019 (2)
C6	0.037 (2)	0.040 (3)	0.042 (3)	0.005 (2)	0.008 (2)	0.017 (2)
C7	0.052 (3)	0.060 (4)	0.046 (3)	0.017 (3)	0.015 (2)	0.026 (3)
C8	0.064 (4)	0.088 (6)	0.057 (4)	0.013 (4)	0.025 (3)	0.032 (4)
C9	0.045 (3)	0.054 (4)	0.063 (4)	0.008 (3)	0.018 (3)	0.003 (3)
C10	0.049 (3)	0.047 (3)	0.072 (4)	0.011 (3)	0.020 (3)	0.021 (3)

Cl1—Hg1	2.3875 (19)	C5—N1	1.323 (8)
Cl2—Hg1	2.4579 (19)	C5—N2	1.381 (8)
N1—Hg1	2.369 (6)	C6—N3	1.341 (8)
N2—H2B	0.95 (14)	C6—N2	1.383 (8)
N3—Hg1	2.290 (6)	C6—C7	1.398 (9)
C1—N1	1.349 (10)	C7—C8	1.397 (11)
C1—C2	1.363 (13)	C7—H7	0.9300
C1—H1	0.9300	C8—C9	1.352 (14)
C2—C3	1.390 (14)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.369 (12)
C3—C4	1.372 (11)	C9—H9	0.9300
C3—H3	0.9300	C10—N3	1.362 (9)
C4—C5	1.399 (9)	C10—H10	0.9300
C4—H4	0.9300
N1—Hg1—Cl1	112.30 (15)	N2—C6—C7	116.6 (5)
N1—Hg1—Cl2	94.92 (15)	C8—C7—C6	119.0 (7)
N3—Hg1—Cl1	112.21 (15)	C8—C7—H7	120.5
N3—Hg1—Cl2	123.92 (14)	C6—C7—H7	120.5
N3—Hg1—N1	82.4 (2)	C9—C8—C7	119.0 (7)
Cl1—Hg1—Cl2	120.14 (7)	C9—C8—H8	120.6
N1—C1—C2	123.8 (8)	C7—C8—H8	120.4
N1—C1—H1	118.1	C8—C9—C10	119.9 (7)
C2—C1—H1	118.1	C8—C9—H9	120.0
C1—C2—C3	117.9 (8)	C10—C9—H9	120.1
C1—C2—H2	121.0	N3—C10—C9	122.5 (7)
C3—C2—H2	121.0	N3—C10—H10	118.7
C4—C3—C2	118.7 (8)	C9—C10—H10	118.8
C4—C3—H3	120.6	C5—N1—C1	118.4 (7)
C2—C3—H3	120.7	C5—N1—Hg1	125.5 (4)
C3—C4—C5	119.9 (7)	C1—N1—Hg1	115.7 (5)
C3—C4—H4	120.1	C6—N2—C5	136.0 (5)
C5—C4—H4	120.0	C6—N2—H2B	109 (8)
N1—C5—N2	122.3 (6)	C5—N2—H2B	115 (8)
N1—C5—C4	121.1 (6)	C6—N3—C10	118.2 (6)
N2—C5—C4	116.6 (6)	C6—N3—Hg1	127.3 (4)
N3—C6—N2	122.1 (6)	C10—N3—Hg1	114.4 (5)
N3—C6—C7	121.3 (6)
C1—N1—Hg1—N3	−169.7 (6)	C6—C7—C8—C9	2.0 (12)
C5—N1—Hg1—N3	17.3 (5)	C7—C8—C9—C10	−0.9 (13)
C1—N1—Hg1—Cl1	−58.7 (6)	C8—C9—C10—N3	0.6 (12)
C1—N1—Hg1—Cl2	66.7 (6)	N2—C5—N1—C1	179.1 (7)
C5—N1—Hg1—Cl1	128.2 (5)	C4—C5—N1—C1	−2.6 (10)
C5—N1—Hg1—Cl2	−106.3 (5)	N2—C5—N1—Hg1	−8.1 (9)
C6—N3—Hg1—N1	−15.5 (5)	C4—C5—N1—Hg1	170.3 (5)
C10—N3—Hg1—N1	168.0 (5)	C2—C1—N1—C5	1.9 (13)
C6—N3—Hg1—Cl1	−126.5 (5)	C2—C1—N1—Hg1	−171.6 (7)
C10—N3—Hg1—Cl1	57.0 (5)	N3—C6—N2—C5	17.7 (11)
C6—N3—Hg1—Cl2	75.3 (5)	C7—C6—N2—C5	−164.1 (7)
C10—N3—Hg1—Cl2	−101.2 (5)	N1—C5—N2—C6	−15.3 (11)
N1—C1—C2—C3	−1.4 (15)	C4—C5—N2—C6	166.3 (7)
C1—C2—C3—C4	1.5 (14)	N2—C6—N3—C10	−179.2 (6)
C2—C3—C4—C5	−2.3 (12)	C7—C6—N3—C10	2.7 (9)
C3—C4—C5—N1	2.8 (10)	N2—C6—N3—Hg1	4.5 (8)
C3—C4—C5—N2	−178.7 (7)	C7—C6—N3—Hg1	−173.7 (5)
N3—C6—C7—C8	−3.0 (10)	C9—C10—N3—C6	−1.5 (10)
N2—C6—C7—C8	178.7 (7)	C9—C10—N3—Hg1	175.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl2i	0.95 (16)	2.41 (16)	3.345 (6)	169 (13)

Cl1—Hg1	2.3875 (19)
Cl2—Hg1	2.4579 (19)
N1—Hg1	2.369 (6)
N3—Hg1	2.290 (6)

N1—Hg1—Cl1	112.30 (15)
N1—Hg1—Cl2	94.92 (15)
N3—Hg1—Cl1	112.21 (15)
N3—Hg1—Cl2	123.92 (14)
N3—Hg1—N1	82.4 (2)
Cl1—Hg1—Cl2	120.14 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl2i	0.95 (16)	2.41 (16)	3.345 (6)	169 (13)

Symmetry code: (i) .