Dibromido(di-2-pyridylamine-κN,N')mercury(II).

In the mol-ecule of the title compound, [HgBr(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 Br atoms. In the crystal structure, inter-molecular N-H⋯Br hydrogen bonds link the mol-ecules into centrosymmetric dimers. There are π-π contacts between the pyridine rings [centroid-centroid distances = 3.9662 (5) and 3.9321 (4) Å]. There also exists a C-H⋯π contact between the pyridine CH group and a pyridine ring.

Related literature

For related literature, see: Ahmadi et al. (2008 ▶); Kalateh 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: Xie et al. (2004 ▶); Hughes et al. (1985 ▶).

Experimental

Crystal data

[HgBr2(C10n class="Species">H9N3)]

M = 531.59

Triclinic,

a = 8.1284 (16) Å

b = 8.7645 (18) Å

c = 9.912 (2) Å

α = 113.45 (3)°

β = 98.41 (3)°

γ = 97.79 (3)°

V = 626.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 18.65 mm−1

T = 120 (2) K

0.40 × 0.35 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: numerical (shape of crystal determined optically) (X-SHAPE and X-RED; Stoe & Cie, 2005 ▶)T min = 0.016, T max = 0.080

7839 measured reflections

3350 independent reflections

3234 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.140

S = 1.15

3350 reflections

145 parameters

H-atom parameters constrained

Δρmax = 4.33 e Å−3

Δρmin = −6.54 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/S1600536808038129/hk2575sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038129/hk2575Isup2.hkl

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

[HgBr2(C10H9N3)]	Z = 2
Mr = 531.59	F000 = 480
Triclinic, P1	Dx = 2.820 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.1284 (16) Å	Cell parameters from 1657 reflections
b = 8.7645 (18) Å	θ = 2.3–29.2º
c = 9.912 (2) Å	µ = 18.65 mm−1
α = 113.45 (3)º	T = 120 (2) K
β = 98.41 (3)º	Prism, colorless
γ = 97.79 (3)º	0.40 × 0.35 × 0.25 mm
V = 626.1 (3) Å3

Bruker SMART CCD area-detector diffractometer	3350 independent reflections
Radiation source: fine-focus sealed tube	3234 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.087
T = 120(2) K	θmax = 29.2º
φ and ω scans	θmin = 2.3º
Absorption correction: numerical(shape of crystal determined optically)	h = −11→11
Tmin = 0.016, Tmax = 0.080	k = −11→10
7839 measured reflections	l = −12→13

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0882P)2 + 2.3955P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.059
3350 reflections	Δρmax = 4.33 e Å−3
145 parameters	Δρmin = −6.54 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.28140 (3)	0.22806 (4)	0.84793 (3)	0.02226 (15)
Br1	0.03376 (10)	0.29535 (11)	0.71493 (10)	0.0259 (2)
Br2	0.58403 (10)	0.34148 (10)	0.83842 (9)	0.0219 (2)
N1	0.2053 (9)	0.1755 (9)	1.0425 (8)	0.0195 (12)
N2	0.3018 (9)	−0.0818 (8)	0.9915 (8)	0.0190 (12)
H2A	0.3426	−0.1362	1.0395	0.023*
N3	0.3006 (9)	−0.0591 (8)	0.7601 (8)	0.0192 (12)
C1	0.1347 (11)	0.2988 (10)	1.1369 (11)	0.0239 (15)
H1	0.1098	0.3845	1.1096	0.029*
C2	0.0991 (11)	0.3023 (11)	1.2678 (11)	0.0248 (16)
H2	0.0516	0.3881	1.3288	0.030*
C3	0.1363 (11)	0.1728 (11)	1.3080 (10)	0.0247 (15)
H3	0.1151	0.1727	1.3977	0.030*
C4	0.2037 (11)	0.0462 (11)	1.2157 (10)	0.0225 (14)
H4	0.2279	−0.0412	1.2407	0.027*
C5	0.2355 (9)	0.0519 (10)	1.0815 (9)	0.0178 (13)
C6	0.3175 (9)	−0.1477 (10)	0.8430 (9)	0.0172 (13)
C7	0.3535 (10)	−0.3113 (10)	0.7834 (10)	0.0215 (14)
H7	0.3679	−0.3693	0.8437	0.026*
C8	0.3671 (11)	−0.3850 (11)	0.6355 (10)	0.0249 (15)
H8	0.3886	−0.4940	0.5944	0.030*
C9	0.3485 (12)	−0.2952 (11)	0.5481 (10)	0.0262 (16)
H9	0.3575	−0.3414	0.4479	0.031*
C10	0.3158 (11)	−0.1340 (12)	0.6165 (10)	0.0248 (16)
H10	0.3034	−0.0731	0.5587	0.030*

	U11	U22	U33	U12	U13	U23
Hg1	0.0242 (2)	0.0212 (2)	0.0290 (2)	0.00845 (13)	0.00573 (13)	0.01720 (14)
Br1	0.0239 (4)	0.0253 (4)	0.0341 (4)	0.0070 (3)	0.0012 (3)	0.0194 (3)
Br2	0.0237 (4)	0.0208 (4)	0.0267 (4)	0.0057 (3)	0.0061 (3)	0.0151 (3)
N1	0.023 (3)	0.016 (3)	0.019 (3)	0.006 (2)	0.001 (2)	0.008 (2)
N2	0.026 (3)	0.015 (3)	0.022 (3)	0.007 (2)	0.004 (2)	0.013 (2)
N3	0.024 (3)	0.016 (3)	0.018 (3)	0.005 (2)	0.002 (2)	0.009 (2)
C1	0.025 (4)	0.015 (3)	0.032 (4)	0.005 (3)	0.003 (3)	0.011 (3)
C2	0.024 (3)	0.020 (3)	0.030 (4)	0.007 (3)	0.007 (3)	0.009 (3)
C3	0.029 (4)	0.024 (4)	0.022 (3)	0.006 (3)	0.009 (3)	0.010 (3)
C4	0.026 (3)	0.021 (3)	0.024 (4)	0.005 (3)	0.003 (3)	0.012 (3)
C5	0.014 (3)	0.017 (3)	0.020 (3)	0.001 (2)	0.002 (2)	0.007 (3)
C6	0.013 (3)	0.016 (3)	0.020 (3)	−0.002 (2)	−0.002 (2)	0.009 (3)
C7	0.024 (3)	0.017 (3)	0.024 (4)	0.004 (3)	0.004 (3)	0.010 (3)
C8	0.027 (4)	0.022 (4)	0.023 (4)	0.005 (3)	0.002 (3)	0.008 (3)
C9	0.037 (4)	0.021 (4)	0.017 (3)	0.005 (3)	0.003 (3)	0.006 (3)
C10	0.030 (4)	0.029 (4)	0.020 (3)	0.008 (3)	0.004 (3)	0.015 (3)

Br1—Hg1	2.5106 (11)	C5—N1	1.327 (10)
Br2—Hg1	2.5549 (11)	C5—N2	1.393 (10)
N1—Hg1	2.301 (7)	C6—N3	1.342 (10)
N2—H2A	0.8600	C6—N2	1.384 (10)
N3—Hg1	2.350 (7)	C6—C7	1.408 (11)
C1—C2	1.360 (13)	C7—C8	1.376 (12)
C1—N1	1.376 (11)	C7—H7	0.9300
C1—H1	0.9300	C8—C9	1.389 (13)
C2—C3	1.398 (13)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.385 (12)
C3—C4	1.368 (12)	C9—H9	0.9300
C3—H3	0.9300	C10—N3	1.342 (11)
C4—C5	1.410 (11)	C10—H10	0.9300
C4—H4	0.9300
N1—Hg1—N3	81.1 (2)	C2—C3—H3	119.9
N1—Hg1—Br1	109.13 (17)	C3—C4—C5	118.2 (8)
N3—Hg1—Br1	117.16 (17)	C3—C4—H4	120.9
N1—Hg1—Br2	125.41 (17)	C5—C4—H4	120.9
N3—Hg1—Br2	96.23 (18)	N1—C5—N2	121.7 (7)
Br1—Hg1—Br2	119.68 (3)	N1—C5—C4	122.9 (7)
C1—N1—Hg1	114.3 (5)	N2—C5—C4	115.4 (7)
C5—N1—Hg1	128.2 (6)	N3—C6—N2	121.6 (7)
C5—N1—C1	117.2 (7)	N3—C6—C7	121.6 (7)
C6—N2—C5	135.0 (7)	N2—C6—C7	116.9 (7)
C6—N2—H2A	112.5	C8—C7—C6	119.6 (8)
C5—N2—H2A	112.5	C8—C7—H7	120.2
C6—N3—Hg1	126.5 (5)	C6—C7—H7	120.2
C10—N3—Hg1	115.6 (6)	C7—C8—C9	119.4 (8)
C10—N3—C6	117.4 (7)	C7—C8—H8	120.3
C2—C1—N1	123.6 (8)	C9—C8—H8	120.3
C2—C1—H1	118.1	C8—C9—C10	117.2 (8)
N1—C1—H1	118.3	C8—C9—H9	121.4
C1—C2—C3	117.9 (8)	C10—C9—H9	121.4
C1—C2—H2	121.0	N3—C10—C9	124.8 (8)
C3—C2—H2	121.1	N3—C10—H10	117.5
C4—C3—C2	120.2 (8)	C9—C10—H10	117.7
C4—C3—H3	120.0
C1—N1—Hg1—N3	−166.6 (6)	C6—C7—C8—C9	1.3 (12)
C5—N1—Hg1—N3	20.2 (6)	C7—C8—C9—C10	−0.3 (13)
C1—N1—Hg1—Br1	−50.8 (6)	C8—C9—C10—N3	−0.1 (14)
C5—N1—Hg1—Br1	136.0 (6)	N2—C5—N1—C1	178.0 (7)
C1—N1—Hg1—Br2	102.0 (5)	C4—C5—N1—C1	−2.2 (11)
C5—N1—Hg1—Br2	−71.1 (7)	N2—C5—N1—Hg1	−9.0 (10)
C10—N3—Hg1—N1	168.0 (6)	C4—C5—N1—Hg1	170.8 (6)
C6—N3—Hg1—N1	−20.2 (6)	C2—C1—N1—C5	1.8 (12)
C6—N3—Hg1—Br1	−127.2 (6)	C2—C1—N1—Hg1	−172.2 (7)
C10—N3—Hg1—Br1	61.0 (6)	N3—C6—N2—C5	16.3 (13)
C6—N3—Hg1—Br2	104.8 (6)	C7—C6—N2—C5	−164.2 (8)
C10—N3—Hg1—Br2	−67.0 (6)	N1—C5—N2—C6	−16.8 (13)
N1—C1—C2—C3	−0.2 (13)	C4—C5—N2—C6	163.3 (8)
C1—C2—C3—C4	−1.0 (13)	C9—C10—N3—C6	−0.4 (13)
C2—C3—C4—C5	0.6 (12)	C9—C10—N3—Hg1	172.2 (7)
C3—C4—C5—N1	1.0 (12)	N2—C6—N3—C10	−179.2 (7)
C3—C4—C5—N2	−179.1 (7)	C7—C6—N3—C10	1.4 (11)
N3—C6—C7—C8	−1.8 (11)	N2—C6—N3—Hg1	9.2 (10)
N2—C6—C7—C8	178.7 (7)	C7—C6—N3—Hg1	−170.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br2i	0.86	2.62	3.472 (3)	170
C2—H2···Cg3ii	0.93	3.20	3.587 (3)	107

Br1—Hg1	2.5106 (11)
Br2—Hg1	2.5549 (11)
N1—Hg1	2.301 (7)
N3—Hg1	2.350 (7)

N1—Hg1—N3	81.1 (2)
N1—Hg1—Br1	109.13 (17)
N3—Hg1—Br1	117.16 (17)
N1—Hg1—Br2	125.41 (17)
N3—Hg1—Br2	96.23 (18)
Br1—Hg1—Br2	119.68 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br2i	0.86	2.62	3.472 (3)	170
C2—H2⋯Cg3ii	0.93	3.20	3.587 (3)	107

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the N3/C6–C10 ring.