Dichlorido(6-methyl-2,2'-bipyridine-κN,N')mercury(II).

In the mol-ecule of the title compound, [HgCl(2)(C(11)H(10)N(2))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from a 6-methyl-2,2'-bipyridine ligand and two Cl atoms. There is a π-π contact between the pyridine rings [centroid-centroid distance = 3.9758 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh, Ebadi et al. (2008 ▶); Ahmadi, Khalighi et al. (2008 ▶); Ahmadi, Kalateh, Abedi et al. (2008 ▶); Kalateh, Ahmadi et al. (2008 ▶); Kalateh, Ebadi et al. (2008 ▶); Khalighi et al. (2008 ▶); Khavasi et al. (2008 ▶); Tadayon Pour et al. (2008 ▶); Yousefi, Rashidi Vahid et al. (2008 ▶); Yousefi, Tadayon Pour et al. (2008 ▶); Yousefi, Khalighi et al. (2008 ▶). For related structures, see: Chen et al. (2006 ▶); Liu et al. (2004 ▶).

Experimental

Crystal data

[HgCl2(C11H10N2)]

M = 441.70

Monoclinic,

a = 9.4742 (19) Å

b = 16.164 (3) Å

c = 8.2107 (16) Å

β = 105.70 (3)°

V = 1210.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 13.13 mm−1

T = 120 (2) K

0.50 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: numerical via shape of crystal determined optically ( and ; Stoe & Cie, 2005 ▶) T min = 0.108, T max = 0.307

14334 measured reflections

3263 independent reflections

2925 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.092

wR(F 2) = 0.197

S = 1.14

3263 reflections

147 parameters

H-atom parameters constrained

Δρmax = 1.39 e Å−3

Δρmin = −1.12 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/S1600536808032777/hk2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032777/hk2551Isup2.hkl

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

[HgCl2(C11H10N2)]	F(000) = 816
Mr = 441.70	Dx = 2.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1234 reflections
a = 9.4742 (19) Å	θ = 2.2–29.2°
b = 16.164 (3) Å	µ = 13.13 mm−1
c = 8.2107 (16) Å	T = 120 K
β = 105.70 (3)°	Needle, colorless
V = 1210.4 (4) Å3	0.50 × 0.15 × 0.09 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3263 independent reflections
Radiation source: fine-focus sealed tube	2925 reflections with I > 2σ(I)
graphite	Rint = 0.100
φ and ω scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: numerical via shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)	h = −12→11
Tmin = 0.108, Tmax = 0.307	k = −22→22
14334 measured reflections	l = −9→11

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)] = 0.092	H-atom parameters constrained
wR(F2) = 0.197	w = 1/[σ2(Fo2) + (0.1638P)2 + 3.9978P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.005
3263 reflections	Δρmax = 1.39 e Å−3
147 parameters	Δρmin = −1.12 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: 0.020 (2)

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	0.81647 (4)	0.05913 (2)	0.29276 (5)	0.0248 (3)
Cl1	0.8330 (3)	−0.00698 (17)	0.5642 (3)	0.0244 (5)
Cl2	0.7288 (3)	−0.03469 (19)	0.0569 (4)	0.0299 (6)
N1	0.6912 (9)	0.1861 (5)	0.3103 (11)	0.0187 (16)
N2	0.9427 (10)	0.1664 (6)	0.2138 (11)	0.0227 (18)
C1	0.4897 (12)	0.1134 (9)	0.3776 (14)	0.032 (2)
H1A	0.4493	0.0873	0.2700	0.048*
H1B	0.4123	0.1261	0.4285	0.048*
H1C	0.5585	0.0767	0.4500	0.048*
C2	0.5650 (11)	0.1903 (7)	0.3534 (13)	0.024 (2)
C3	0.5077 (11)	0.2686 (8)	0.3770 (14)	0.030 (2)
H3	0.4196	0.2725	0.4058	0.036*
C4	0.5820 (12)	0.3385 (8)	0.3573 (14)	0.029 (2)
H4	0.5457	0.3900	0.3764	0.034*
C5	0.7106 (11)	0.3335 (6)	0.3093 (15)	0.024 (2)
H5	0.7601	0.3811	0.2924	0.028*
C6	0.7649 (11)	0.2543 (6)	0.2868 (11)	0.0175 (17)
C7	0.9018 (10)	0.2430 (6)	0.2327 (11)	0.0175 (17)
C8	0.9819 (11)	0.3114 (7)	0.2004 (15)	0.025 (2)
H8	0.9522	0.3648	0.2181	0.030*
C9	1.1063 (13)	0.2995 (8)	0.1417 (14)	0.031 (2)
H9	1.1609	0.3437	0.1191	0.037*
C10	1.1450 (11)	0.2146 (8)	0.1183 (13)	0.028 (2)
H10	1.2258	0.2029	0.0784	0.033*
C11	1.0615 (10)	0.1513 (7)	0.1553 (12)	0.0211 (19)
H11	1.0870	0.0969	0.1399	0.025*

	U11	U22	U33	U12	U13	U23
Hg1	0.0291 (4)	0.0223 (4)	0.0234 (4)	−0.00241 (12)	0.0075 (2)	−0.00050 (12)
Cl1	0.0251 (11)	0.0254 (12)	0.0226 (10)	0.0004 (9)	0.0061 (8)	0.0033 (9)
Cl2	0.0307 (13)	0.0297 (13)	0.0264 (12)	−0.0031 (11)	0.0032 (10)	−0.0077 (11)
N1	0.012 (3)	0.021 (4)	0.020 (4)	−0.001 (3)	0.000 (3)	−0.003 (3)
N2	0.022 (4)	0.032 (5)	0.014 (3)	0.001 (3)	0.004 (3)	−0.007 (3)
C1	0.019 (4)	0.050 (7)	0.023 (5)	−0.005 (5)	0.002 (4)	0.002 (5)
C2	0.014 (4)	0.034 (5)	0.023 (5)	0.002 (4)	0.001 (3)	0.002 (4)
C3	0.015 (4)	0.044 (7)	0.026 (5)	0.001 (4)	−0.003 (4)	−0.012 (5)
C4	0.025 (5)	0.039 (6)	0.020 (4)	0.005 (4)	0.003 (4)	−0.004 (4)
C5	0.018 (4)	0.018 (4)	0.031 (5)	0.003 (3)	0.000 (4)	−0.005 (4)
C6	0.025 (4)	0.014 (4)	0.008 (3)	0.000 (3)	−0.005 (3)	0.001 (3)
C7	0.018 (4)	0.023 (4)	0.009 (3)	−0.002 (3)	0.000 (3)	0.004 (3)
C8	0.018 (4)	0.030 (5)	0.025 (5)	−0.006 (4)	0.003 (3)	0.000 (4)
C9	0.025 (5)	0.042 (7)	0.018 (4)	0.004 (4)	−0.008 (4)	0.017 (5)
C10	0.017 (4)	0.045 (7)	0.019 (4)	0.004 (4)	0.001 (3)	0.004 (5)
C11	0.019 (4)	0.027 (5)	0.017 (4)	0.008 (4)	0.003 (3)	0.009 (4)

Cl1—Hg1	2.438 (2)	C5—C6	1.410 (13)
Cl2—Hg1	2.423 (3)	C5—H5	0.9300
N1—Hg1	2.394 (9)	C6—N1	1.347 (13)
N2—Hg1	2.297 (10)	C6—C7	1.492 (14)
C1—C2	1.473 (17)	C7—N2	1.319 (14)
C1—H1A	0.9600	C7—C8	1.406 (14)
C1—H1B	0.9600	C8—C9	1.402 (17)
C1—H1C	0.9600	C8—H8	0.9300
C2—N1	1.338 (13)	C9—C10	1.446 (18)
C2—C3	1.411 (17)	C9—H9	0.9300
C3—C4	1.363 (18)	C10—C11	1.377 (16)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.381 (16)	C11—N2	1.360 (13)
C4—H4	0.9300	C11—H11	0.9300
Cl2—Hg1—Cl1	112.32 (10)	C3—C4—C5	120.6 (11)
N1—Hg1—Cl1	103.4 (2)	C3—C4—H4	119.7
N1—Hg1—Cl2	121.1 (2)	C5—C4—H4	119.7
N2—Hg1—Cl1	132.8 (2)	C4—C5—C6	118.1 (10)
N2—Hg1—Cl2	109.8 (2)	C4—C5—H5	121.0
N2—Hg1—N1	71.0 (3)	C6—C5—H5	121.0
C2—N1—Hg1	123.6 (7)	N1—C6—C5	120.3 (10)
C2—N1—C6	122.1 (9)	N1—C6—C7	117.9 (9)
C6—N1—Hg1	114.1 (6)	C5—C6—C7	121.8 (9)
C7—N2—Hg1	118.9 (7)	N2—C7—C8	121.7 (9)
C7—N2—C11	120.4 (10)	N2—C7—C6	117.2 (9)
C11—N2—Hg1	120.6 (8)	C8—C7—C6	121.1 (9)
C2—C1—H1A	109.5	C9—C8—C7	120.2 (11)
C2—C1—H1B	109.5	C9—C8—H8	119.9
H1A—C1—H1B	109.5	C7—C8—H8	119.9
C2—C1—H1C	109.5	C8—C9—C10	116.3 (11)
H1A—C1—H1C	109.5	C8—C9—H9	121.8
H1B—C1—H1C	109.5	C10—C9—H9	121.8
N1—C2—C3	119.1 (10)	C11—C10—C9	119.6 (10)
N1—C2—C1	119.5 (10)	C11—C10—H10	120.2
C3—C2—C1	121.3 (10)	C9—C10—H10	120.2
C4—C3—C2	119.8 (11)	N2—C11—C10	121.7 (10)
C4—C3—H3	120.1	N2—C11—H11	119.2
C2—C3—H3	120.1	C10—C11—H11	119.2
C2—N1—Hg1—Cl1	−51.3 (8)	C5—C6—C7—C8	−0.5 (13)
C2—N1—Hg1—Cl2	75.5 (8)	N2—C7—C8—C9	2.0 (15)
C2—N1—Hg1—N2	177.6 (8)	C6—C7—C8—C9	−176.9 (9)
C6—N1—Hg1—Cl1	123.3 (6)	C7—C8—C9—C10	−0.2 (14)
C6—N1—Hg1—Cl2	−109.9 (6)	C8—C9—C10—C11	−0.7 (14)
C6—N1—Hg1—N2	−7.7 (6)	C9—C10—C11—N2	0.0 (15)
C7—N2—Hg1—Cl1	−83.2 (8)	C3—C2—N1—C6	−0.7 (14)
C7—N2—Hg1—Cl2	124.8 (7)	C1—C2—N1—C6	−179.9 (9)
C7—N2—Hg1—N1	7.6 (7)	C3—C2—N1—Hg1	173.6 (7)
C11—N2—Hg1—Cl1	94.0 (7)	C1—C2—N1—Hg1	−5.7 (13)
C11—N2—Hg1—Cl2	−58.0 (7)	C5—C6—N1—C2	0.7 (14)
C11—N2—Hg1—N1	−175.2 (8)	C7—C6—N1—C2	−177.8 (8)
N1—C2—C3—C4	−0.7 (16)	C5—C6—N1—Hg1	−174.0 (7)
C1—C2—C3—C4	178.5 (10)	C7—C6—N1—Hg1	7.5 (10)
C2—C3—C4—C5	2.0 (16)	C8—C7—N2—C11	−2.7 (14)
C3—C4—C5—C6	−2.0 (16)	C6—C7—N2—C11	176.2 (8)
C4—C5—C6—N1	0.6 (14)	C8—C7—N2—Hg1	174.5 (7)
C4—C5—C6—C7	179.1 (9)	C6—C7—N2—Hg1	−6.6 (11)
N1—C6—C7—N2	−1.0 (12)	C10—C11—N2—C7	1.7 (14)
C5—C6—C7—N2	−179.4 (9)	C10—C11—N2—Hg1	−175.4 (7)
N1—C6—C7—C8	177.9 (9)

Cl1—Hg1	2.438 (2)
Cl2—Hg1	2.423 (3)
N1—Hg1	2.394 (9)
N2—Hg1	2.297 (10)

Cl2—Hg1—Cl1	112.32 (10)
N1—Hg1—Cl1	103.4 (2)
N1—Hg1—Cl2	121.1 (2)
N2—Hg1—Cl1	132.8 (2)
N2—Hg1—Cl2	109.8 (2)
N2—Hg1—N1	71.0 (3)