[Benzyl(2-pyridylmeth-yl)amine]dichloridomercury(II).

The Hg atom in the title compound, [HgCl(2)(C(13)H(14)N(2))], adopts a distorted tetra-hedral geometry, being ligated by two N atoms of the benzyl(2-pyridylmeth-yl)amine (bpma) ligand and two Cl atoms. The dihedral angle between the least-squares planes through the chelate ring and Cl-Hg-Cl atoms is 85.4 (1)°. The phenyl ring on the bpma ligand is twisted out of the pyridine plane, forming a dihedral angle of 76.0 (3)°. Disorder in this ring is also noted with two coplanar conformations having equal site occupancies.

Related literature

For general background, see: Ojida et al. (2004 ▶). For background on luminescent mercury compounds, see: Yordanov & Roundhill (1998 ▶); Das et al. (2003 ▶); Haneline et al. (2002 ▶); Atoub et al. (2007 ▶). For related structures, see Kim et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

[HgCl2(C13H14N2)]

M = 469.75

Monoclinic,

a = 13.1045 (3) Å

b = 13.8233 (3) Å

c = 8.3201 (2) Å

β = 91.135 (1)°

V = 1506.87 (6) Å3

Z = 4

Mo Kα radiation

μ = 10.55 mm−1

T = 174 (2) K

0.12 × 0.11 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.290, T max = 0.345

16218 measured reflections

3751 independent reflections

3258 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.045

S = 1.03

3751 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.82 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040695/tk2337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040695/tk2337Isup2.hkl

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

[HgCl2(C13H14N2)]	F(000) = 880
Mr = 469.75	Dx = 2.071 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6766 reflections
a = 13.1045 (3) Å	θ = 2.9–28.3°
b = 13.8233 (3) Å	µ = 10.55 mm−1
c = 8.3201 (2) Å	T = 174 K
β = 91.135 (1)°	Block, colourless
V = 1506.87 (6) Å3	0.12 × 0.11 × 0.1 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3258 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.027
Absorption correction: multi-scan (SADABS; Bruker, 2002)	θmax = 28.3°, θmin = 1.6°
Tmin = 0.290, Tmax = 0.345	h = −15→17
16218 measured reflections	k = −18→18
3751 independent reflections	l = −11→11

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.021	w = 1/[σ2(Fo2) + (0.0166P)2 + 1.085P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.045	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.69 e Å−3
3751 reflections	Δρmin = −0.82 e Å−3
195 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	Occ. (<1)
Hg1	0.212834 (9)	0.445793 (9)	0.162371 (14)	0.03875 (5)
N1	0.05042 (19)	0.39726 (18)	0.2591 (3)	0.0381 (6)
C2	−0.0374 (3)	0.3898 (3)	0.1748 (4)	0.0468 (8)
H2	−0.0373	0.4027	0.0651	0.056*
C3	−0.1277 (3)	0.3639 (3)	0.2442 (5)	0.0550 (9)
H3	−0.1876	0.3594	0.1829	0.066*
C4	−0.1275 (3)	0.3447 (3)	0.4051 (5)	0.0540 (9)
H4	−0.1878	0.3278	0.4551	0.065*
C5	−0.0378 (3)	0.3505 (2)	0.4930 (4)	0.0462 (8)
H5	−0.0365	0.3367	0.6024	0.055*
C6	0.0507 (2)	0.3773 (2)	0.4161 (4)	0.0361 (6)
C7	0.1496 (2)	0.3892 (3)	0.5091 (4)	0.0463 (8)
H7A	0.1518	0.4535	0.5559	0.056*
H7B	0.1517	0.3428	0.5966	0.056*
N8	0.24046 (19)	0.37557 (19)	0.4098 (3)	0.0348 (5)
H8	0.247 (3)	0.312 (3)	0.391 (4)	0.050 (10)*
C9	0.3360 (3)	0.4089 (3)	0.4915 (4)	0.0526 (9)
H9A	0.346	0.3736	0.5913	0.063*
H9B	0.3302	0.4771	0.5173	0.063*
C10	0.4254 (2)	0.3936 (3)	0.3868 (4)	0.0411 (7)
C11	0.4612 (3)	0.4674 (3)	0.2916 (5)	0.0605 (11)
H11	0.4251	0.5248	0.3025	0.073*
C12	0.5321 (13)	0.473 (2)	0.1940 (19)	0.052 (4)	0.50 (4)
H12	0.5498	0.5298	0.1412	0.062*	0.50 (4)
C13	0.5821 (16)	0.384 (3)	0.173 (3)	0.066 (7)	0.50 (4)
H13	0.6361	0.381	0.1022	0.079*	0.50 (4)
C14	0.5540 (15)	0.304 (2)	0.252 (2)	0.065 (6)	0.50 (4)
H14	0.5862	0.2457	0.2295	0.078*	0.50 (4)
C12A	0.5511 (15)	0.4286 (18)	0.1850 (19)	0.053 (5)	0.50 (4)
H12A	0.5797	0.4699	0.1099	0.063*	0.50 (4)
C13A	0.5883 (19)	0.337 (2)	0.199 (4)	0.075 (7)	0.50 (4)
H13A	0.6418	0.3166	0.1356	0.09*	0.50 (4)
C14A	0.5477 (16)	0.2739 (17)	0.307 (4)	0.076 (6)	0.50 (4)
H14A	0.5745	0.2125	0.3251	0.092*	0.50 (4)
C15	0.4712 (3)	0.3051 (3)	0.3786 (6)	0.0694 (12)
H15	0.4541	0.2522	0.4419	0.083*
Cl1	0.22317 (7)	0.61872 (6)	0.18426 (10)	0.0500 (2)
Cl2	0.23761 (8)	0.36292 (6)	−0.08585 (10)	0.0558 (2)

	U11	U22	U33	U12	U13	U23
Hg1	0.03980 (7)	0.04565 (7)	0.03086 (7)	−0.00518 (5)	0.00190 (5)	0.00120 (5)
N1	0.0373 (14)	0.0425 (14)	0.0344 (13)	−0.0046 (11)	0.0005 (11)	0.0004 (11)
C2	0.0426 (19)	0.058 (2)	0.0401 (18)	−0.0070 (16)	−0.0046 (15)	−0.0019 (16)
C3	0.0386 (19)	0.065 (2)	0.062 (2)	−0.0093 (16)	−0.0023 (17)	−0.0102 (19)
C4	0.044 (2)	0.055 (2)	0.064 (2)	−0.0122 (16)	0.0201 (17)	−0.0085 (18)
C5	0.048 (2)	0.0474 (18)	0.0439 (18)	−0.0041 (15)	0.0132 (15)	0.0000 (15)
C6	0.0383 (16)	0.0338 (14)	0.0365 (16)	0.0025 (13)	0.0069 (13)	−0.0041 (13)
C7	0.0431 (19)	0.068 (2)	0.0275 (16)	0.0032 (16)	0.0037 (13)	−0.0025 (15)
N8	0.0344 (13)	0.0390 (13)	0.0309 (13)	0.0012 (11)	−0.0024 (10)	−0.0015 (11)
C9	0.043 (2)	0.080 (2)	0.0349 (18)	−0.0055 (18)	−0.0100 (15)	−0.0113 (17)
C10	0.0325 (16)	0.062 (2)	0.0285 (15)	−0.0043 (14)	−0.0112 (12)	−0.0002 (14)
C11	0.046 (2)	0.085 (3)	0.050 (2)	−0.021 (2)	−0.0177 (18)	0.013 (2)
C12	0.031 (5)	0.083 (11)	0.040 (5)	−0.018 (7)	−0.014 (4)	0.018 (7)
C13	0.028 (7)	0.12 (2)	0.053 (6)	0.000 (11)	−0.008 (6)	0.011 (14)
C14	0.031 (8)	0.103 (18)	0.062 (9)	0.025 (10)	0.006 (6)	0.009 (8)
C12A	0.045 (11)	0.063 (14)	0.051 (6)	−0.013 (8)	−0.007 (8)	0.013 (10)
C13A	0.032 (8)	0.101 (18)	0.093 (18)	−0.006 (10)	0.013 (8)	−0.027 (13)
C14A	0.044 (7)	0.073 (9)	0.111 (18)	−0.005 (6)	−0.001 (10)	−0.003 (9)
C15	0.039 (2)	0.073 (3)	0.096 (3)	0.0058 (19)	−0.016 (2)	0.002 (2)
Cl1	0.0564 (5)	0.0400 (4)	0.0539 (5)	−0.0043 (4)	0.0104 (4)	−0.0042 (4)
Cl2	0.0875 (7)	0.0456 (4)	0.0346 (4)	0.0015 (4)	0.0060 (4)	−0.0064 (3)

Hg1—N8	2.298 (2)	C9—H9A	0.97
Hg1—N1	2.387 (3)	C9—H9B	0.97
Hg1—Cl2	2.3895 (8)	C10—C15	1.365 (5)
Hg1—Cl1	2.4010 (8)	C10—C11	1.380 (5)
N1—C6	1.334 (4)	C11—C12	1.248 (17)
N1—C2	1.340 (4)	C11—C12A	1.58 (2)
C2—C3	1.375 (5)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.403 (19)
C3—C4	1.365 (5)	C12—H12	0.93
C3—H3	0.93	C13—C14	1.35 (3)
C4—C5	1.375 (5)	C13—H13	0.93
C4—H4	0.93	C14—C15	1.524 (19)
C5—C6	1.386 (4)	C14—H14	0.93
C5—H5	0.93	C12A—C13A	1.37 (3)
C6—C7	1.506 (4)	C12A—H12A	0.93
C7—N8	1.475 (4)	C13A—C14A	1.36 (2)
C7—H7A	0.97	C13A—H13A	0.93
C7—H7B	0.97	C14A—C15	1.25 (2)
N8—C9	1.486 (4)	C14A—H14A	0.93
N8—H8	0.89 (4)	C15—H15	0.93
C9—C10	1.489 (5)
N8—Hg1—N1	72.83 (9)	N8—C9—C10	110.7 (3)
N8—Hg1—Cl2	123.37 (7)	N8—C9—H9A	109.5
N1—Hg1—Cl2	107.11 (7)	C10—C9—H9A	109.5
N8—Hg1—Cl1	110.18 (7)	N8—C9—H9B	109.5
N1—Hg1—Cl1	107.67 (7)	C10—C9—H9B	109.5
Cl2—Hg1—Cl1	122.31 (3)	H9A—C9—H9B	108.1
C6—N1—C2	118.8 (3)	C15—C10—C11	118.6 (4)
C6—N1—Hg1	113.8 (2)	C15—C10—C9	120.6 (4)
C2—N1—Hg1	127.4 (2)	C11—C10—C9	120.8 (4)
N1—C2—C3	122.5 (3)	C12—C11—C10	133.4 (14)
N1—C2—H2	118.7	C10—C11—C12A	109.8 (9)
C3—C2—H2	118.7	C12—C11—H11	113.3
C4—C3—C2	118.5 (3)	C10—C11—H11	113.3
C4—C3—H3	120.7	C11—C12—C13	112.4 (18)
C2—C3—H3	120.7	C11—C12—H12	123.8
C3—C4—C5	119.7 (3)	C13—C12—H12	123.8
C3—C4—H4	120.1	C14—C13—C12	122 (2)
C5—C4—H4	120.1	C14—C13—H13	119.1
C4—C5—C6	119.0 (3)	C12—C13—H13	119.1
C4—C5—H5	120.5	C13—C14—C15	122.2 (14)
C6—C5—H5	120.5	C13—C14—H14	118.9
N1—C6—C5	121.4 (3)	C15—C14—H14	118.9
N1—C6—C7	117.8 (3)	C13A—C12A—C11	122.2 (15)
C5—C6—C7	120.8 (3)	C13A—C12A—H12A	118.9
N8—C7—C6	113.2 (2)	C11—C12A—H12A	118.9
N8—C7—H7A	108.9	C14A—C13A—C12A	120 (2)
C6—C7—H7A	108.9	C14A—C13A—H13A	119.8
N8—C7—H7B	108.9	C12A—C13A—H13A	119.8
C6—C7—H7B	108.9	C15—C14A—C13A	115 (2)
H7A—C7—H7B	107.8	C15—C14A—H14A	122.5
C7—N8—C9	112.7 (2)	C13A—C14A—H14A	122.5
C7—N8—Hg1	109.47 (18)	C14A—C15—C10	133.5 (13)
C9—N8—Hg1	113.3 (2)	C10—C15—C14	111.4 (11)
C7—N8—H8	108 (2)	C14A—C15—H15	101.8
C9—N8—H8	107 (2)	C10—C15—H15	124.3
Hg1—N8—H8	106 (2)	C14—C15—H15	124.3

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···Cl2i	0.89 (4)	2.44 (4)	3.297 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯Cl2i	0.89 (4)	2.44 (4)	3.297 (3)	163 (3)

Symmetry code: (i) .