Dibromido(di-2-pyridylamine-κ2N,N′)mercury(II)

Kalateh, K.; Norouzi, A.; Ebadi, A.; Ahmadi, R.; Amani, V.

doi:10.1107/S1600536808038129

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1583-m1584

doi:10.1107/S1600536808038129

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Dibromido(di-2-pyridylamine-κ²N,N′)mercury(II)

Khadijeh Kalateh,^a Ali Norouzi,^b Amin Ebadi,^c Roya Ahmadi ^a and Vahid Amani ^a ^*

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, ^bIslamic Azad University, Izeh Branch, Khozestan, Iran, and ^cDepartment of Chemistry, Islamic Azad University, Kazeroon Branch, Fars, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 13 November 2008; accepted 16 November 2008; online 20 November 2008)

In the molecule of the title compound, [HgBr₂(C₁₀H₉N₃)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the chelating di-2-pyridylamine ligand and by two Br atoms. In the crystal structure, intermolecular N—H⋯Br hydrogen bonds link the molecules 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(C₁₀H₉N₃)]
M_r = 531.59
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.140
S = 1.15
3350 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 4.33 e Å⁻³
Δρ_min = −6.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) -x+1, -y, -z+2; (ii) -x+2, -y, -z. Cg3 is the centroid of the N3/C6–C10 ring.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038129/hk2575sup1.cif

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

checkCIF report

Comment top

Recently, we reported the syntheses and crystal structures of [Hg(4,4'-dmbpy) I₂], (II), (Yousefi, Tadayon Pour et al., 2008), [Hg(5,5'-dmbpy)I₂], (III), (Tadayon Pour, et al., 2008), [Hg(dmphen)I₂], (IV), (Yousefi, Rashidi Vahid et al., 2008), {[HgCl(dm4bt)]₂(µ-Cl)₂}, (V), (Khavasi et al., 2008), [Hg(6-mbpy)Cl₂], (VI), (Ahmadi et al., 2008) and [{HgBr(4,4'-dmbpy)}₂(µ-Br)₂], (VII), (Kalateh et al., 2008) [where 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbpy is 5,5'-dimethyl-2,2'- bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, dmphen is 4,7-diphenyl-1,10- phenanthroline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are two Hg^II complexes, with formula, [Hg(N—N)Br₂], such as [Hg(TPA)Br₂], (VIII), (Xie et al., 2004) and [Hg(TPD)Br₂], (IX), (Hughes et al., 1985) [where TPA is tris(2-pyridyl)amine and TPD is N,N,N',N'-Tetramethyl-o-phenylenediamine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (Fig. 1), the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from di-2-pyridylamine and two Br atoms. The Hg-Br and Hg-N bond lengths and angles (Table 1) are within normal ranges, as in (VIII).

In the crystal structure, intermolecular N-H···Br hydrogen bonds link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the pyridine rings Cg2···Cg2ⁱ and Cg2···Cg3ⁱⁱ [symmetry codes: (i) x, -y, 2 - z, (ii) 1 - x,- y, 2 - z, where Cg2 and Cg3 are centroids of the rings A (N1/C1-C5) and B (N3/C6-C10), respectively] may further stabilize the structure, with centroid-centroid distances of 3.9662 (5) %A and 3.9321 (4) %A, respectively. There also exists a C—H···π contact (Table 1) between the pyridine CH group and pyridine ring.

Related literature top

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 top

For the preparation of the title compound, (I), a solution of di-2-pyridylamine (0.25 g, 1.43 mmol) in methanol (20 ml) was added to a solution of HgBr₂ (0.51 g, 1.43 mmol) in acetonitrile (20 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless prismatic crystals of the title compound were isolated (yield; 0.55 g, 72.3%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound.

Dibromido(di-2-pyridylamine-κ²N,N')mercury(II) top

Crystal data top

[HgBr₂(C₁₀H₉N₃)]	Z = 2
M_r = 531.59	F(000) = 480
Triclinic, P1	D_x = 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 = 2.3–29.2°
c = 9.912 (2) Å	µ = 18.65 mm⁻¹
α = 113.45 (3)°	T = 120 K
β = 98.41 (3)°	Prism, colorless
γ = 97.79 (3)°	0.40 × 0.35 × 0.25 mm
V = 626.1 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3350 independent reflections
Radiation source: fine-focus sealed tube	3234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.3°
Absorption correction: numerical (shape of crystal determined optically)	h = −11→11
T_min = 0.016, T_max = 0.080	k = −11→10
7839 measured reflections	l = −12→13

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0882P)² + 2.3955P] where P = (F_o² + 2F_c²)/3
3350 reflections	(Δ/σ)_max = 0.059
145 parameters	Δρ_max = 4.33 e Å⁻³
0 restraints	Δρ_min = −6.54 e Å⁻³

Crystal data top

[HgBr₂(C₁₀H₉N₃)]	γ = 97.79 (3)°
M_r = 531.59	V = 626.1 (3) Å³
Triclinic, P1	Z = 2
a = 8.1284 (16) Å	Mo Kα radiation
b = 8.7645 (18) Å	µ = 18.65 mm⁻¹
c = 9.912 (2) Å	T = 120 K
α = 113.45 (3)°	0.40 × 0.35 × 0.25 mm
β = 98.41 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3350 independent reflections
Absorption correction: numerical (shape of crystal determined optically)	3234 reflections with I > 2σ(I)
T_min = 0.016, T_max = 0.080	R_int = 0.087
7839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.15	Δρ_max = 4.33 e Å⁻³
3350 reflections	Δρ_min = −6.54 e Å⁻³
145 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[HgBr₂(C₁₀H₉N₃)]
M_r	531.59
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.1284 (16), 8.7645 (18), 9.912 (2)
α, β, γ (°)	113.45 (3), 98.41 (3), 97.79 (3)
V (Å³)	626.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	18.65
Crystal size (mm)	0.40 × 0.35 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Numerical (shape of crystal determined optically)
T_min, T_max	0.016, 0.080
No. of measured, independent and observed [I > 2σ(I)] reflections	7839, 3350, 3234
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.140, 1.15
No. of reflections	3350
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	4.33, −6.54

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br2ⁱ	0.86	2.620	3.472 (3)	170
C2—H2···Cg3ⁱⁱ	0.93	3.197	3.587 (3)	107

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+2, −y, −z.

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

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