Dibromido(2,9-dimethyl-1,10-phenanthroline-κN,N')mercury(II).

In the mol-ecule of the title compound, [HgBr(2)(C(14)H(12)N(2))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand and by two Br atoms. In the crystal structure, weak inter-molecular C-H⋯Br hydrogen bonds link the mol-ecules 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 = 568.65

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.183

S = 1.12

4161 reflections

172 parameters

H-atom parameters constrained

Δρmax = 1.23 e Å−3

Δρmin = −2.40 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/S1600536809009994/hk2645sup1.cif

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

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

[HgBr2(C14H12N2)]	F(000) = 1040
Mr = 568.65	Dx = 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

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

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(Fo2) + (0.0825P)2 + 6.5584P] where P = (Fo2 + 2Fc2)/3
4161 reflections	(Δ/σ)max = 0.007
172 parameters	Δρmax = 1.23 e Å−3
0 restraints	Δρmin = −2.40 e Å−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	0.21080 (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)

	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)

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)

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

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) .