Dibromido(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)mercury(II)

Alizadeh, R.; Heidari, A.; Ahmadi, R.; Amani, V.

doi:10.1107/S1600536809009994

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m483-m484

doi:10.1107/S1600536809009994

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Dibromido(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)mercury(II)

Robabeh Alizadeh,^a ^* Amene Heidari,^b Roya Ahmadi ^c and Vahid Amani ^c

^aSchool of Chemistry, Damghan University of Basic Sciences, Damghan, Iran, ^bDepartment of Chemistry, University of Zabol, Zabol, Iran, and ^cIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: alizadeh@dubs.ac.ir

(Received 17 March 2009; accepted 18 March 2009; online 2 April 2009)

In the molecule of the title compound, [HgBr₂(C₁₄H₁₂N₂)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand and by two Br atoms. In the crystal structure, weak intermolecular C—H⋯Br hydrogen bonds link the molecules into chains along the b axis. There are π–π contacts between the phenanthroline rings [centroid–centroid distances = 3.806 (4), 3.819 (4), 3.739 (3), 3.690 (3), 3.619 (4) and 3.674 (3) Å].

Related literature

For related structures, see: Ahmadi et al. (2008 ); Craig et al. (1974 ); Hughes et al. (1985 ); Kalateh, Ebadi et al. (2008 ); Kalateh, Norouzi et al. (2008 ); Perlepes et al. (1995 ); Tadayon Pour et al. (2008 ); Xie et al. (2004 ); Yousefi et al. (2009 ); Yousefi, Rashidi Vahid et al. (2008 ); Yousefi, Tadayon Pour et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[HgBr₂(C₁₄H₁₂N₂)]
M_r = 568.65
Monoclinic, P 2₁ /c
a = 7.8587 (7) Å
b = 10.5556 (8) Å
c = 18.7304 (13) Å
β = 97.517 (6)°
V = 1540.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 15.17 mm⁻¹
T = 298 K
0.49 × 0.44 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 )T_min = 0.008, T_max = 0.022
11121 measured reflections
4161 independent reflections
3006 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.183
S = 1.12
4161 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 1.23 e Å⁻³
Δρ_min = −2.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Hg1—Br2	2.5053 (16)
Hg1—Br1	2.5156 (17)
N1—Hg1	2.345 (8)
N2—Hg1	2.340 (8)

Br2—Hg1—Br1	116.23 (6)
N1—Hg1—Br1	109.6 (2)
N1—Hg1—Br2	115.7 (2)
N2—Hg1—Br1	117.3 (2)
N2—Hg1—Br2	118.2 (2)
N2—Hg1—N1	71.2 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Br2ⁱ	0.96	2.85	3.812 (18)	178
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809009994/hk2645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009994/hk2645Isup2.hkl

checkCIF report

Comment top

There are several Hg^II complexes, with formula, [Hg(N—N)X₂], (X=Br, Cl and I), such as [Hg(TPA)Br₂], (II), (Xie et al., 2004), [Hg(TPD)Br₂], (III), (Hughes et al., 1985), [Hg(NH(py)₂)Br₂], (IV), (Kalateh, Norouzi et al., 2008), [Hg(6-mbpy)Cl₂], (V), (Ahmadi et al., 2008), [Hg(NH(py)₂)Cl₂], (VI), (Yousefi, Allahgholi Ghasri et al., 2009), [Hg(4,4'-dmbpy)I₂], (VII), (Yousefi, Tadayon Pour et al., 2008), [Hg(5,5'-dmbpy)I₂], (VIII), (Tadayon Pour et al., 2008) and [Hg(dmphen)I₂], (IX), (Yousefi, Rashidi Vahid et al., 2008) [where TPA is tris(2-pyridyl)amine, TPD is N,N,N',N'-Tetramethyl-o-phenylenediamine, NH(py)₂ is di-2-pyridylamine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine and dmphen is 4,7-diphenyl-1,10-phenanthroline] have been synthesized and characterized by single-crystal X-ray diffraction methods.

There are also several Hg^II dimer complexes, with formula, [{HgBr(N—N)}₂(µ-Br)₂], such as [{HgBr(bipy)}₂(µ-Br)₂], (X), (Craig et al., 1974),[{HgBr(pquin)}₂(µ-Br)₂], (XI), (Perlepes et al., 1995) and [{HgBr(4,4'-dmbpy)}₂(µ-Br)₂], (XII), (Kalateh, Ebadi et al., 2008) [where bipy is 2,2'-bipyridine and pquin is 2-(2'-pyridyl)quinoxaline] 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 2,9-dimethyl-1,10-phenanthroline and by two Br atoms. The Hg-Br and Hg-N bond lengths (Allen et al., 1987) and angles (Table 1) are within normal ranges, and comparable with the corresponding values in (II) and (III).

In the crystal structure, weak intermolecular C-H···Br hydrogen bonds (Table 2) link the molecules into chains along the b-axis, in which they may be effective in the stabilization of the crystal structure (Fig. 2). The π-π contacts between the phenanthroline rings, Cg3···Cg2ⁱ, Cg3···Cg3ⁱⁱ, Cg4···Cg1ⁱ, Cg4···Cg2ⁱ, Cg4···Cg3ⁱⁱ and Cg4···Cg4ⁱ [symmetry codes: (i) 1 - x, -y, -z; (ii) 2 - x, -y, -z, where Cg1, Cg2, Cg3 and Cg4 are centroids of the rings A (Hg1/N1/N2/C13/C14), B (N1/C2-C5/C14), C (N2/C8-C11/C13) and D (C5-C8/C13/C14), respectively] may further stabilize the structure, with centroid-centroid distances of 3.806 (4), 3.819 (4), 3.739 (3), 3.690 (3), 3.619 (4) and 3.674 (3) Å, respectively.

Related literature top

For related structures, see: Ahmadi et al. (2008); Craig et al. (1974); Hughes et al. (1985); Kalateh, Ebadi et al. (2008); Kalateh, Norouzi et al. (2008); Perlepes et al. (1995); Tadayon Pour et al. (2008); Xie et al. (2004); Yousefi, Allahgholi Ghasri et al. (2009); Yousefi, Rashidi Vahid et al. (2008); Yousefi, Tadayon Pour et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, (I), a solution of 2,9-dimethyl-1,10-phenanthroline (0.25 g, 1.20 mmol) in methanol (10 ml) was added to a solution of HgBr₂ (0.43 g, 1.20 mmol) in methanol (20 ml) at room temperature. Crystals suitable for X-ray analysis were obtained by methanol diffusion to a colorless solution in DMSO and isolated after one week (yield; 0.51 g, 74.7%).

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 40% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Dibromido(2,9-dimethyl-1,10-phenanthroline-κ²N,N')mercury(II) top

Crystal data top

[HgBr₂(C₁₄H₁₂N₂)]	F(000) = 1040
M_r = 568.65	D_x = 2.452 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1005 reflections
a = 7.8587 (7) Å	θ = 2.2–29.2°
b = 10.5556 (8) Å	µ = 15.17 mm⁻¹
c = 18.7304 (13) Å	T = 298 K
β = 97.517 (6)°	Block, colorless
V = 1540.4 (2) Å³	0.49 × 0.44 × 0.26 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4161 independent reflections
Radiation source: fine-focus sealed tube	3006 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.2°
Absorption correction: numerical Shape of crystal determined optically	h = −10→10
T_min = 0.008, T_max = 0.022	k = −13→14
11121 measured reflections	l = −19→25

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0825P)² + 6.5584P] where P = (F_o² + 2F_c²)/3
4161 reflections	(Δ/σ)_max = 0.007
172 parameters	Δρ_max = 1.23 e Å⁻³
0 restraints	Δρ_min = −2.40 e Å⁻³

Crystal data top

[HgBr₂(C₁₄H₁₂N₂)]	V = 1540.4 (2) Å³
M_r = 568.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8587 (7) Å	µ = 15.17 mm⁻¹
b = 10.5556 (8) Å	T = 298 K
c = 18.7304 (13) Å	0.49 × 0.44 × 0.26 mm
β = 97.517 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4161 independent reflections
Absorption correction: numerical Shape of crystal determined optically	3006 reflections with I > 2σ(I)
T_min = 0.008, T_max = 0.022	R_int = 0.093
11121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.12	Δρ_max = 1.23 e Å⁻³
4161 reflections	Δρ_min = −2.40 e Å⁻³
172 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	0.21080 (7)	0.79014 (4)	0.39095 (3)	0.05349 (18)
Br1	−0.0605 (2)	0.8266 (2)	0.30622 (9)	0.0836 (5)
Br2	0.4351 (2)	0.95948 (12)	0.39430 (9)	0.0783 (5)
N1	0.3074 (11)	0.5823 (8)	0.3777 (5)	0.0424 (18)
N2	0.1876 (11)	0.6779 (8)	0.4970 (5)	0.0376 (17)
C1	0.376 (3)	0.6301 (15)	0.2566 (8)	0.086 (5)
H1A	0.4518	0.6985	0.2730	0.103*
H1B	0.2641	0.6632	0.2400	0.103*
H1C	0.4200	0.5866	0.2179	0.103*
C2	0.3645 (15)	0.5411 (10)	0.3164 (5)	0.043 (2)
C3	0.4185 (17)	0.4150 (11)	0.3120 (7)	0.056 (3)
H3	0.4595	0.3857	0.2706	0.067*
C4	0.4101 (14)	0.3354 (11)	0.3692 (7)	0.052 (3)
H4	0.4445	0.2515	0.3659	0.062*
C5	0.3508 (12)	0.3775 (9)	0.4323 (6)	0.040 (2)
C6	0.3390 (15)	0.2991 (10)	0.4931 (8)	0.054 (3)
H6	0.3745	0.2151	0.4925	0.065*
C7	0.2778 (17)	0.3444 (11)	0.5512 (8)	0.059 (3)
H7	0.2710	0.2909	0.5901	0.071*
C8	0.2221 (14)	0.4732 (10)	0.5553 (6)	0.045 (2)
C9	0.1555 (16)	0.5221 (12)	0.6139 (6)	0.052 (3)
H9	0.1428	0.4704	0.6531	0.063*
C10	0.1082 (17)	0.6457 (15)	0.6147 (7)	0.060 (3)
H10	0.0646	0.6789	0.6546	0.072*
C11	0.1255 (15)	0.7242 (11)	0.5544 (6)	0.049 (2)
C12	0.078 (2)	0.8630 (13)	0.5530 (8)	0.068 (4)
H12A	−0.0089	0.8790	0.5129	0.081*
H12B	0.1773	0.9133	0.5483	0.081*
H12C	0.0340	0.8847	0.5970	0.081*
C13	0.2361 (12)	0.5538 (9)	0.4964 (5)	0.0353 (18)
C14	0.2975 (11)	0.5055 (9)	0.4335 (6)	0.038 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0797 (3)	0.0314 (2)	0.0497 (3)	0.00853 (18)	0.0099 (2)	0.00815 (17)
Br1	0.0775 (9)	0.1107 (13)	0.0618 (9)	0.0161 (9)	0.0063 (7)	0.0348 (9)
Br2	0.1172 (12)	0.0377 (6)	0.0795 (10)	−0.0148 (7)	0.0114 (9)	0.0107 (6)
N1	0.059 (5)	0.029 (4)	0.039 (4)	−0.004 (3)	0.002 (4)	−0.004 (3)
N2	0.046 (4)	0.034 (4)	0.033 (4)	0.002 (3)	0.005 (3)	0.001 (3)
C1	0.148 (16)	0.056 (8)	0.059 (9)	0.013 (9)	0.030 (10)	−0.006 (7)
C2	0.062 (6)	0.038 (5)	0.029 (5)	0.000 (4)	0.003 (4)	−0.005 (4)
C3	0.080 (8)	0.040 (6)	0.050 (6)	0.001 (5)	0.016 (6)	−0.015 (5)
C4	0.046 (6)	0.034 (5)	0.074 (8)	0.005 (4)	0.004 (5)	−0.007 (5)
C5	0.037 (5)	0.031 (4)	0.050 (6)	0.002 (4)	−0.005 (4)	0.001 (4)
C6	0.055 (6)	0.034 (5)	0.071 (8)	0.006 (4)	−0.001 (6)	0.015 (5)
C7	0.073 (8)	0.036 (6)	0.064 (8)	−0.006 (5)	−0.002 (6)	0.023 (5)
C8	0.050 (6)	0.041 (5)	0.041 (5)	−0.010 (4)	−0.002 (4)	0.013 (4)
C9	0.064 (7)	0.052 (6)	0.039 (6)	−0.008 (5)	0.000 (5)	0.007 (5)
C10	0.059 (7)	0.078 (9)	0.045 (6)	−0.015 (6)	0.020 (5)	−0.013 (6)
C11	0.057 (6)	0.045 (6)	0.043 (6)	0.001 (5)	0.001 (5)	−0.002 (4)
C12	0.102 (11)	0.048 (7)	0.055 (7)	0.008 (7)	0.014 (7)	−0.008 (6)
C13	0.036 (4)	0.032 (4)	0.037 (5)	−0.003 (3)	−0.001 (4)	0.006 (4)
C14	0.031 (4)	0.035 (4)	0.045 (5)	−0.001 (3)	−0.005 (4)	0.005 (4)

Geometric parameters (Å, º) top

Hg1—Br2	2.5053 (16)	C6—H6	0.9300
Hg1—Br1	2.5156 (17)	C7—C8	1.433 (16)
N1—Hg1	2.345 (8)	C7—H7	0.9300
N2—Hg1	2.340 (8)	C8—C9	1.377 (17)
C1—C2	1.474 (19)	C8—C13	1.409 (13)
C1—H1A	0.9600	C9—C10	1.36 (2)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.422 (18)
C2—N1	1.359 (13)	C10—H10	0.9300
C2—C3	1.403 (15)	C11—N2	1.330 (14)
C3—C4	1.370 (18)	C11—C12	1.512 (18)
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.400 (17)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—C14	1.416 (13)	C13—N2	1.365 (12)
C5—C6	1.421 (16)	C13—C14	1.425 (15)
C6—C7	1.33 (2)	C14—N1	1.333 (13)

Br2—Hg1—Br1	116.23 (6)	C7—C6—C5	120.9 (10)
N1—Hg1—Br1	109.6 (2)	C7—C6—H6	119.6
N1—Hg1—Br2	115.7 (2)	C5—C6—H6	119.6
N2—Hg1—Br1	117.3 (2)	C6—C7—C8	122.0 (11)
N2—Hg1—Br2	118.2 (2)	C6—C7—H7	119.0
N2—Hg1—N1	71.2 (3)	C8—C7—H7	119.0
C14—N1—C2	121.8 (9)	C9—C8—C13	118.3 (10)
C14—N1—Hg1	115.7 (7)	C9—C8—C7	123.4 (11)
C2—N1—Hg1	122.5 (7)	C13—C8—C7	118.4 (11)
C11—N2—C13	119.4 (9)	C10—C9—C8	120.2 (11)
C11—N2—Hg1	125.3 (7)	C10—C9—H9	119.9
C13—N2—Hg1	115.2 (6)	C8—C9—H9	119.9
C2—C1—H1A	109.5	C9—C10—C11	119.8 (12)
C2—C1—H1B	109.5	C9—C10—H10	120.1
H1A—C1—H1B	109.5	C11—C10—H10	120.1
C2—C1—H1C	109.5	N2—C11—C10	120.8 (11)
H1A—C1—H1C	109.5	N2—C11—C12	117.3 (11)
H1B—C1—H1C	109.5	C10—C11—C12	121.9 (11)
N1—C2—C3	119.4 (10)	C11—C12—H12A	109.5
N1—C2—C1	119.9 (10)	C11—C12—H12B	109.5
C3—C2—C1	120.7 (11)	H12A—C12—H12B	109.5
C4—C3—C2	119.3 (11)	C11—C12—H12C	109.5
C4—C3—H3	120.3	H12A—C12—H12C	109.5
C2—C3—H3	120.3	H12B—C12—H12C	109.5
C3—C4—C5	121.5 (10)	N2—C13—C8	121.5 (10)
C3—C4—H4	119.3	N2—C13—C14	118.4 (8)
C5—C4—H4	119.3	C8—C13—C14	120.1 (9)
C4—C5—C14	116.7 (10)	N1—C14—C5	121.3 (10)
C4—C5—C6	123.8 (10)	N1—C14—C13	119.4 (9)
C14—C5—C6	119.5 (10)	C5—C14—C13	119.2 (9)

N1—C2—C3—C4	1.0 (18)	C13—C14—N1—C2	−179.8 (9)
C1—C2—C3—C4	178.4 (13)	C5—C14—N1—Hg1	179.7 (7)
C2—C3—C4—C5	−0.8 (19)	C13—C14—N1—Hg1	−2.0 (11)
C3—C4—C5—C14	1.0 (16)	C3—C2—N1—C14	−1.6 (16)
C3—C4—C5—C6	179.8 (11)	C1—C2—N1—C14	−178.9 (12)
C4—C5—C6—C7	−178.5 (11)	C3—C2—N1—Hg1	−179.2 (9)
C14—C5—C6—C7	0.3 (17)	C1—C2—N1—Hg1	3.4 (16)
C5—C6—C7—C8	−0.3 (19)	C10—C11—N2—C13	−0.4 (16)
C6—C7—C8—C9	178.8 (12)	C12—C11—N2—C13	178.6 (10)
C6—C7—C8—C13	−1.1 (18)	C10—C11—N2—Hg1	176.5 (8)
C13—C8—C9—C10	−1.3 (17)	C12—C11—N2—Hg1	−4.5 (15)
C7—C8—C9—C10	178.8 (12)	C8—C13—N2—C11	0.0 (15)
C8—C9—C10—C11	0.9 (19)	C14—C13—N2—C11	178.2 (9)
C9—C10—C11—N2	0.0 (19)	C8—C13—N2—Hg1	−177.2 (7)
C9—C10—C11—C12	−178.9 (12)	C14—C13—N2—Hg1	1.0 (11)
C9—C8—C13—N2	0.9 (15)	C11—N2—Hg1—N1	−178.4 (9)
C7—C8—C13—N2	−179.2 (10)	C13—N2—Hg1—N1	−1.4 (6)
C9—C8—C13—C14	−177.3 (9)	C11—N2—Hg1—Br2	71.9 (9)
C7—C8—C13—C14	2.6 (15)	C13—N2—Hg1—Br2	−111.1 (6)
C4—C5—C14—N1	−1.6 (14)	C11—N2—Hg1—Br1	−75.5 (9)
C6—C5—C14—N1	179.6 (9)	C13—N2—Hg1—Br1	101.6 (6)
C4—C5—C14—C13	−179.9 (9)	C14—N1—Hg1—N2	1.7 (7)
C6—C5—C14—C13	1.2 (14)	C2—N1—Hg1—N2	179.6 (9)
N2—C13—C14—N1	0.7 (14)	C14—N1—Hg1—Br2	114.7 (7)
C8—C13—C14—N1	178.9 (9)	C2—N1—Hg1—Br2	−67.5 (8)
N2—C13—C14—C5	179.1 (8)	C14—N1—Hg1—Br1	−111.4 (7)
C8—C13—C14—C5	−2.7 (14)	C2—N1—Hg1—Br1	66.4 (8)
C5—C14—N1—C2	1.9 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br2ⁱ	0.96	2.85	3.812 (18)	178

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[HgBr₂(C₁₄H₁₂N₂)]
M_r	568.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.8587 (7), 10.5556 (8), 18.7304 (13)
β (°)	97.517 (6)
V (Å³)	1540.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	15.17
Crystal size (mm)	0.49 × 0.44 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Numerical Shape of crystal determined optically
T_min, T_max	0.008, 0.022
No. of measured, independent and observed [I > 2σ(I)] reflections	11121, 4161, 3006
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.183, 1.12
No. of reflections	4161
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.23, −2.40

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

Hg1—Br2	2.5053 (16)	N1—Hg1	2.345 (8)
Hg1—Br1	2.5156 (17)	N2—Hg1	2.340 (8)

Br2—Hg1—Br1	116.23 (6)	N2—Hg1—Br1	117.3 (2)
N1—Hg1—Br1	109.6 (2)	N2—Hg1—Br2	118.2 (2)
N1—Hg1—Br2	115.7 (2)	N2—Hg1—N1	71.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br2ⁱ	0.96	2.85	3.812 (18)	178.00

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

We are grateful to Damghan University of Basic Sciences for financial support.

References

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