[Benz-yl(2-pyridyl-methyl-idene)amine]-dichloridomercury(II).

The Hg(II) ion in the title complex, [HgCl(2)(C(13)H(12)N(2))], adopts a distorted tetra-hedral geometry being coordinated by two Cl anions and by two N atoms of the benz-yl(2-pyridyl-methyl-ene)amine ligand. The Cl-Hg-Cl plane is twisted at 70.1 (1)° from the mean plane of the chelate ring. In the crystal structure, inter-molecular π-π inter-actions [centroid-centroid distance = 3.793 (3) Å] between the aromatic rings link the mol-ecules into zigzag chains extending along [010].

Related literature

For chemosensors of mercury ions, see: Zhou et al. (2010 ▶). For electroluminescent devices, see: Fan et al. (2009 ▶). For the crystal structures and luminescence of related Hg complexes, see: Kim et al. (2008 ▶, 2010 ▶); Seo et al. (2009a ▶,b ▶).

Experimental

Crystal data

[HgCl2(C13H12N2)]

M = 467.74

Monoclinic,

a = 8.2736 (1) Å

b = 11.8828 (2) Å

c = 14.1191 (2) Å

β = 94.343 (1)°

V = 1384.11 (3) Å3

Z = 4

Mo Kα radiation

μ = 11.49 mm−1

T = 295 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.094, T max = 0.118

14227 measured reflections

3432 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.056

S = 1.03

3432 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −1.61 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035889/cv2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035889/cv2760Isup2.hkl

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

[HgCl2(C13H12N2)]	F(000) = 872
Mr = 467.74	Dx = 2.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5055 reflections
a = 8.2736 (1) Å	θ = 2.2–27.7°
b = 11.8828 (2) Å	µ = 11.49 mm−1
c = 14.1191 (2) Å	T = 295 K
β = 94.343 (1)°	Block, colourless
V = 1384.11 (3) Å3	0.22 × 0.2 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2797 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 28.3°, θmin = 2.2°
Tmin = 0.094, Tmax = 0.118	h = −11→11
14227 measured reflections	k = −15→15
3432 independent reflections	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0212P)2 + 1.9423P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.056	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 1.03 e Å−3
3432 reflections	Δρmin = −1.61 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	0.16420 (2)	0.368809 (15)	0.072427 (10)	0.04946 (7)
N1	0.2879 (3)	0.4688 (2)	0.1992 (2)	0.0354 (7)
C2	0.3837 (5)	0.5579 (3)	0.1919 (3)	0.0457 (9)
H2	0.4039	0.5842	0.1319	0.055*
C3	0.4543 (5)	0.6126 (3)	0.2713 (4)	0.0561 (12)
H3	0.5191	0.6756	0.2645	0.067*
C4	0.4283 (5)	0.5735 (4)	0.3594 (4)	0.0539 (11)
H4	0.474	0.6096	0.4133	0.065*
C5	0.3333 (5)	0.4797 (4)	0.3671 (3)	0.0471 (10)
H5	0.3157	0.4506	0.4266	0.056*
C6	0.2642 (4)	0.4290 (3)	0.2860 (2)	0.0341 (7)
C7	0.1618 (4)	0.3282 (3)	0.2917 (3)	0.0353 (8)
H7	0.1324	0.3039	0.3507	0.042*
N8	0.1135 (4)	0.2744 (2)	0.2183 (2)	0.0350 (6)
C9	0.0108 (5)	0.1746 (3)	0.2275 (3)	0.0430 (9)
H9A	−0.0839	0.1799	0.1828	0.052*
H9B	−0.0258	0.1717	0.2911	0.052*
C10	0.1029 (4)	0.0685 (3)	0.2085 (3)	0.0356 (8)
C11	0.1158 (5)	0.0304 (3)	0.1168 (3)	0.0441 (9)
H11	0.0678	0.0707	0.0657	0.053*
C12	0.1996 (5)	−0.0669 (4)	0.1011 (3)	0.0519 (10)
H12	0.2082	−0.0917	0.0392	0.062*
C13	0.2707 (6)	−0.1275 (3)	0.1754 (4)	0.0520 (10)
H13	0.3261	−0.1937	0.164	0.062*
C14	0.2598 (5)	−0.0905 (4)	0.2664 (3)	0.0517 (10)
H14	0.3086	−0.1312	0.3171	0.062*
C15	0.1764 (5)	0.0073 (3)	0.2832 (3)	0.0442 (9)
H15	0.1696	0.0323	0.3452	0.053*
Cl1	0.39293 (15)	0.30109 (10)	−0.00900 (8)	0.0599 (3)
Cl2	−0.10125 (14)	0.35992 (11)	−0.00837 (8)	0.0607 (3)

	U11	U22	U33	U12	U13	U23
Hg1	0.05046 (10)	0.06449 (12)	0.03322 (8)	−0.00618 (8)	0.00188 (6)	−0.00268 (7)
N1	0.0322 (15)	0.0313 (16)	0.0423 (16)	0.0000 (12)	−0.0001 (12)	0.0043 (13)
C2	0.037 (2)	0.037 (2)	0.063 (3)	−0.0032 (17)	0.0030 (18)	0.0095 (19)
C3	0.034 (2)	0.029 (2)	0.102 (4)	−0.0029 (16)	−0.009 (2)	−0.003 (2)
C4	0.052 (2)	0.042 (2)	0.065 (3)	0.003 (2)	−0.016 (2)	−0.014 (2)
C5	0.049 (2)	0.046 (2)	0.044 (2)	0.0038 (19)	−0.0083 (18)	−0.0101 (18)
C6	0.0327 (17)	0.0312 (18)	0.0380 (18)	0.0056 (15)	−0.0002 (14)	−0.0026 (15)
C7	0.0371 (19)	0.0343 (18)	0.0351 (18)	0.0044 (15)	0.0070 (14)	0.0033 (15)
N8	0.0356 (15)	0.0318 (16)	0.0379 (16)	−0.0032 (13)	0.0044 (12)	0.0003 (13)
C9	0.039 (2)	0.037 (2)	0.055 (2)	−0.0078 (17)	0.0115 (17)	−0.0017 (18)
C10	0.0355 (18)	0.0303 (19)	0.0414 (19)	−0.0094 (15)	0.0058 (15)	−0.0001 (15)
C11	0.054 (2)	0.038 (2)	0.039 (2)	−0.0025 (18)	−0.0003 (17)	0.0024 (17)
C12	0.059 (3)	0.047 (2)	0.050 (2)	−0.002 (2)	0.009 (2)	−0.012 (2)
C13	0.055 (2)	0.031 (2)	0.072 (3)	0.0005 (19)	0.012 (2)	0.003 (2)
C14	0.055 (3)	0.040 (2)	0.059 (3)	−0.005 (2)	−0.003 (2)	0.014 (2)
C15	0.056 (2)	0.042 (2)	0.0353 (19)	−0.0159 (19)	0.0032 (17)	0.0016 (17)
Cl1	0.0642 (7)	0.0605 (7)	0.0570 (6)	0.0117 (6)	0.0186 (5)	0.0063 (5)
Cl2	0.0559 (6)	0.0762 (8)	0.0479 (6)	−0.0078 (6)	−0.0095 (5)	−0.0080 (5)

Hg1—N1	2.321 (3)	C7—H7	0.93
Hg1—Cl2	2.3993 (11)	N8—C9	1.470 (5)
Hg1—N8	2.409 (3)	C9—C10	1.507 (5)
Hg1—Cl1	2.4249 (11)	C9—H9A	0.97
N1—C2	1.331 (5)	C9—H9B	0.97
N1—C6	1.342 (4)	C10—C11	1.382 (5)
C2—C3	1.387 (6)	C10—C15	1.384 (5)
C2—H2	0.93	C11—C12	1.375 (6)
C3—C4	1.359 (7)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.368 (6)
C4—C5	1.373 (6)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.368 (6)
C5—C6	1.379 (5)	C13—H13	0.93
C5—H5	0.93	C14—C15	1.381 (6)
C6—C7	1.473 (5)	C14—H14	0.93
C7—N8	1.258 (5)	C15—H15	0.93
Cg1···Cg2i	3.793 (3)
N1—Hg1—Cl2	136.35 (8)	C7—N8—C9	119.1 (3)
N1—Hg1—N8	71.00 (10)	C7—N8—Hg1	113.8 (2)
Cl2—Hg1—N8	99.99 (8)	C9—N8—Hg1	126.2 (2)
N1—Hg1—Cl1	102.78 (8)	N8—C9—C10	110.9 (3)
Cl2—Hg1—Cl1	118.63 (4)	N8—C9—H9A	109.5
N8—Hg1—Cl1	116.32 (8)	C10—C9—H9A	109.5
C2—N1—C6	118.7 (3)	N8—C9—H9B	109.5
C2—N1—Hg1	125.3 (3)	C10—C9—H9B	109.5
C6—N1—Hg1	115.9 (2)	H9A—C9—H9B	108.1
N1—C2—C3	121.8 (4)	C11—C10—C15	118.7 (4)
N1—C2—H2	119.1	C11—C10—C9	121.1 (4)
C3—C2—H2	119.1	C15—C10—C9	120.2 (3)
C4—C3—C2	119.6 (4)	C12—C11—C10	120.2 (4)
C4—C3—H3	120.2	C12—C11—H11	119.9
C2—C3—H3	120.2	C10—C11—H11	119.9
C3—C4—C5	118.8 (4)	C13—C12—C11	120.8 (4)
C3—C4—H4	120.6	C13—C12—H12	119.6
C5—C4—H4	120.6	C11—C12—H12	119.6
C4—C5—C6	119.5 (4)	C14—C13—C12	119.7 (4)
C4—C5—H5	120.3	C14—C13—H13	120.1
C6—C5—H5	120.3	C12—C13—H13	120.1
N1—C6—C5	121.6 (4)	C13—C14—C15	120.1 (4)
N1—C6—C7	117.5 (3)	C13—C14—H14	120
C5—C6—C7	120.9 (3)	C15—C14—H14	120
N8—C7—C6	121.1 (3)	C14—C15—C10	120.5 (4)
N8—C7—H7	119.5	C14—C15—H15	119.7
C6—C7—H7	119.5	C10—C15—H15	119.7