Dichlorido[N,N-diethyl-N'-(2-pyridyl-methyl-ene)ethane-1,2-diamine]mercury(II).

The Hg atom in the title compound, [HgCl(2)(C(12)H(19)N(3))], adopts a distorted trigonal-bipyramidal geometry, being ligated by two Cl atoms and three N atoms of the N,N-diethyl-N'-(2-pyridylmethyl-ene)ethane-1,2-diamine ligand. The dihedral angle between the HgN(3) and HgCl(2 )least-squares planes is 88.6 (1)°. The Hg-N distances including the pyridine N and the ammonium N atom are about 0.20 Å longer than the Hg-N distance including the imino N atom.

Related literature

For general background to luminescent mercury compounds, see: Elena et al. (2006 ▶); Durantaye et al. (2006 ▶); n class="Gene">Fan et al. (2009 ▶). For the syntheses and structures of these compounds, see: Kim et al. (2008 ▶); Seo et al. (2009 ▶).

Experimental

Crystal data

[HgCl2(C12H19N3)]

M = 476.79

Monoclinic,

a = 8.0028 (5) Å

b = 16.6507 (9) Å

c = 12.4541 (8) Å

β = 101.630 (5)°

V = 1625.47 (17) Å3

Z = 4

Mo Kα radiation

μ = 9.79 mm−1

T = 295 K

0.27 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.085, T max = 0.102

17026 measured reflections

4039 independent reflections

3124 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.059

S = 1.04

4039 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.92 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000103/tk2606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000103/tk2606Isup2.hkl

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

[HgCl2(C12H19N3)]	F(000) = 904
Mr = 476.79	Dx = 1.948 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5949 reflections
a = 8.0028 (5) Å	θ = 2.5–26.4°
b = 16.6507 (9) Å	µ = 9.79 mm−1
c = 12.4541 (8) Å	T = 295 K
β = 101.630 (5)°	Block, colourless
V = 1625.47 (17) Å3	0.27 × 0.24 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3124 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 28.3°, θmin = 2.1°
Tmin = 0.085, Tmax = 0.102	h = −10→10
17026 measured reflections	k = −22→22
4039 independent reflections	l = −14→16

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.026P)2 + 0.5659P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.059	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.71 e Å−3
4039 reflections	Δρmin = −0.92 e Å−3
163 parameters

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.

	x	y	z	Uiso*/Ueq
Hg1	0.208069 (19)	0.190628 (9)	0.561325 (12)	0.05266 (7)
Cl1	0.04834 (16)	0.20511 (8)	0.70474 (10)	0.0766 (3)
Cl2	0.06896 (15)	0.15227 (8)	0.37542 (9)	0.0756 (3)
N1	0.3474 (4)	0.0549 (2)	0.6108 (3)	0.0533 (8)
C2	0.2740 (6)	−0.0156 (3)	0.6201 (4)	0.0654 (11)
H2	0.1555	−0.0177	0.6057	0.078*
C3	0.3629 (7)	−0.0862 (3)	0.6499 (4)	0.0697 (12)
H3	0.3058	−0.1342	0.6553	0.084*
C4	0.5359 (7)	−0.0830 (3)	0.6708 (4)	0.0731 (13)
H4	0.5996	−0.1292	0.6915	0.088*
C5	0.6169 (6)	−0.0108 (3)	0.6612 (3)	0.0659 (11)
H5	0.7353	−0.0078	0.6745	0.079*
C6	0.5184 (5)	0.0570 (2)	0.6313 (3)	0.0527 (9)
C7	0.5949 (5)	0.1352 (3)	0.6185 (3)	0.0584 (10)
H7	0.713	0.1391	0.6283	0.07*
N8	0.5056 (4)	0.19763 (19)	0.5946 (3)	0.0554 (8)
C9	0.5810 (6)	0.2749 (3)	0.5783 (4)	0.0706 (12)
H9A	0.6906	0.2671	0.5578	0.085*
H9B	0.599	0.3057	0.6458	0.085*
C10	0.4618 (7)	0.3196 (2)	0.4886 (4)	0.0721 (14)
H10A	0.5111	0.3715	0.4782	0.087*
H10B	0.451	0.2899	0.4206	0.087*
N11	0.2900 (5)	0.33175 (19)	0.5129 (3)	0.0545 (8)
C12	0.2909 (6)	0.3827 (2)	0.6098 (3)	0.0597 (10)
H12A	0.3544	0.3549	0.6736	0.072*
H12B	0.1743	0.388	0.6197	0.072*
C13	0.3658 (7)	0.4666 (3)	0.6073 (4)	0.0860 (15)
H13A	0.3604	0.4942	0.6742	0.129*
H13B	0.3016	0.496	0.5463	0.129*
H13C	0.4825	0.4627	0.5996	0.129*
C14	0.1738 (7)	0.3608 (3)	0.4138 (4)	0.0836 (15)
H14A	0.1783	0.3241	0.354	0.1*
H14B	0.2134	0.4128	0.3942	0.1*
C15	−0.0096 (8)	0.3686 (4)	0.4267 (5)	0.112 (2)
H15A	−0.0782	0.3881	0.3595	0.168*
H15B	−0.0157	0.4057	0.4849	0.168*
H15C	−0.051	0.3171	0.444	0.168*

	U11	U22	U33	U12	U13	U23
Hg1	0.04281 (9)	0.06545 (11)	0.05013 (10)	−0.00279 (7)	0.01033 (7)	0.00321 (7)
Cl1	0.0616 (7)	0.1078 (9)	0.0680 (7)	−0.0054 (6)	0.0312 (6)	−0.0045 (6)
Cl2	0.0637 (7)	0.0923 (8)	0.0615 (7)	−0.0041 (6)	−0.0097 (6)	−0.0122 (6)
N1	0.0474 (18)	0.065 (2)	0.0478 (18)	0.0010 (15)	0.0114 (15)	0.0030 (15)
C2	0.060 (3)	0.076 (3)	0.066 (3)	−0.002 (2)	0.025 (2)	0.011 (2)
C3	0.082 (3)	0.070 (3)	0.065 (3)	−0.001 (2)	0.033 (3)	0.011 (2)
C4	0.092 (4)	0.068 (3)	0.062 (3)	0.023 (3)	0.024 (3)	0.014 (2)
C5	0.057 (3)	0.080 (3)	0.059 (3)	0.020 (2)	0.009 (2)	0.000 (2)
C6	0.051 (2)	0.067 (2)	0.040 (2)	0.0014 (19)	0.0081 (17)	−0.0043 (17)
C7	0.037 (2)	0.080 (3)	0.058 (2)	0.003 (2)	0.0084 (18)	−0.014 (2)
N8	0.0451 (18)	0.066 (2)	0.057 (2)	−0.0078 (15)	0.0133 (16)	−0.0080 (16)
C9	0.052 (3)	0.069 (3)	0.095 (4)	−0.008 (2)	0.025 (3)	−0.004 (3)
C10	0.089 (4)	0.063 (3)	0.078 (3)	−0.019 (2)	0.050 (3)	−0.005 (2)
N11	0.065 (2)	0.0620 (19)	0.0372 (17)	−0.0039 (16)	0.0116 (16)	0.0066 (14)
C12	0.068 (3)	0.066 (3)	0.047 (2)	0.003 (2)	0.016 (2)	0.0030 (19)
C13	0.115 (4)	0.070 (3)	0.078 (3)	−0.006 (3)	0.031 (3)	−0.012 (3)
C14	0.115 (5)	0.080 (3)	0.048 (3)	−0.004 (3)	−0.003 (3)	0.019 (2)
C15	0.099 (5)	0.117 (5)	0.102 (4)	0.024 (4)	−0.024 (4)	0.018 (4)

Hg1—Cl1	2.4088 (11)	C9—H9A	0.97
Hg1—Cl2	2.4431 (11)	C9—H9B	0.97
Hg1—N1	2.540 (3)	C10—N11	1.480 (6)
Hg1—N8	2.336 (3)	C10—H10A	0.97
Hg1—N11	2.544 (3)	C10—H10B	0.97
N1—C2	1.328 (5)	N11—C14	1.470 (5)
N1—C6	1.341 (5)	N11—C12	1.473 (5)
C2—C3	1.385 (6)	C12—C13	1.524 (6)
C2—H2	0.93	C12—H12A	0.97
C3—C4	1.357 (6)	C12—H12B	0.97
C3—H3	0.93	C13—H13A	0.96
C4—C5	1.384 (6)	C13—H13B	0.96
C4—H4	0.93	C13—H13C	0.96
C5—C6	1.383 (6)	C14—C15	1.514 (8)
C5—H5	0.93	C14—H14A	0.97
C6—C7	1.462 (6)	C14—H14B	0.97
C7—N8	1.262 (5)	C15—H15A	0.96
C7—H7	0.93	C15—H15B	0.96
N8—C9	1.452 (5)	C15—H15C	0.96
C9—C10	1.511 (7)
N8—Hg1—Cl1	122.54 (9)	C10—C9—H9B	109.9
N8—Hg1—Cl2	115.75 (9)	H9A—C9—H9B	108.3
Cl1—Hg1—Cl2	121.35 (4)	N11—C10—C9	113.0 (3)
N8—Hg1—N1	67.63 (11)	N11—C10—H10A	109
Cl1—Hg1—N1	100.47 (8)	C9—C10—H10A	109
Cl2—Hg1—N1	95.24 (8)	N11—C10—H10B	109
N8—Hg1—N11	72.16 (12)	C9—C10—H10B	109
Cl1—Hg1—N11	106.49 (8)	H10A—C10—H10B	107.8
Cl2—Hg1—N11	96.14 (8)	C14—N11—C12	113.3 (4)
N1—Hg1—N11	139.24 (11)	C14—N11—C10	109.3 (4)
C2—N1—C6	117.3 (4)	C12—N11—C10	113.2 (4)
C2—N1—Hg1	128.9 (3)	C14—N11—Hg1	110.7 (3)
C6—N1—Hg1	113.9 (3)	C12—N11—Hg1	107.2 (2)
N1—C2—C3	124.1 (4)	C10—N11—Hg1	102.5 (2)
N1—C2—H2	117.9	N11—C12—C13	116.6 (3)
C3—C2—H2	117.9	N11—C12—H12A	108.1
C4—C3—C2	117.9 (4)	C13—C12—H12A	108.1
C4—C3—H3	121.1	N11—C12—H12B	108.1
C2—C3—H3	121.1	C13—C12—H12B	108.1
C3—C4—C5	119.6 (4)	H12A—C12—H12B	107.3
C3—C4—H4	120.2	C12—C13—H13A	109.5
C5—C4—H4	120.2	C12—C13—H13B	109.5
C6—C5—C4	118.7 (4)	H13A—C13—H13B	109.5
C6—C5—H5	120.6	C12—C13—H13C	109.5
C4—C5—H5	120.6	H13A—C13—H13C	109.5
N1—C6—C5	122.4 (4)	H13B—C13—H13C	109.5
N1—C6—C7	115.8 (3)	N11—C14—C15	113.7 (4)
C5—C6—C7	121.8 (4)	N11—C14—H14A	108.8
N8—C7—C6	122.0 (4)	C15—C14—H14A	108.8
N8—C7—H7	119	N11—C14—H14B	108.8
C6—C7—H7	119	C15—C14—H14B	108.8
C7—N8—C9	122.0 (4)	H14A—C14—H14B	107.7
C7—N8—Hg1	120.6 (3)	C14—C15—H15A	109.5
C9—N8—Hg1	117.2 (3)	C14—C15—H15B	109.5
N8—C9—C10	108.7 (4)	H15A—C15—H15B	109.5
N8—C9—H9A	109.9	C14—C15—H15C	109.5
C10—C9—H9A	109.9	H15A—C15—H15C	109.5
N8—C9—H9B	109.9	H15B—C15—H15C	109.5

Table 1

Selected bond lengths (Å)

Hg1—Cl1	2.4088 (11)
Hg1—Cl2	2.4431 (11)
Hg1—N1	2.540 (3)
Hg1—N8	2.336 (3)
Hg1—N11	2.544 (3)