Dichloridobis(pyridine-2-seleno-lato-κ(2) N,Se)tin(IV).

The title compound, [SnCl2(C5H4NSe)2], is the product of a reaction of 2,2'-dipyridyl diselenide with tin tetra-chloride. The mol-ecule is located about a twofold rotation axis. The coordination environment of the Sn(IV) atom is a distorted octa-hedron, with two bidentate 2-pyridine-seleno-late ligands inclined to each other at an angle of 83.96 (7)°. The two Sn-Cl and two Sn-N bonds are in cis configurations, while the two Sn-Se bonds of 2.5917 (3) Å are in a trans configuration, with an Se-Sn-Se angle of 157.988 (15)°. In the crystal, π-π inter-actions between the pyridine rings [centroid-to-centroid distance of 3.758 (3) Å] and weak inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into chains along the c axis.

Related literature

For metal complexes with 2,2′-dipyridyl dichalcogenides, see: Kadooka et al. (1976a ▶,b ▶); Cheng et al. (1996 ▶); Kienitz et al. (1996 ▶); Bell et al. (2000 ▶); Kita et al. (2001 ▶); Kedarnath et al. (2009 ▶). For syntheses and structures of related tin(IV) compounds, see: Masaki & Matsunami (1976 ▶); Masaki et al. (1978 ▶); Labisbal et al. (1993 ▶); Chopra et al. (1996 ▶); Ismaylova et al. (2012 ▶).

Experimental

Crystal data

[SnCl2(C5H4NSe)2]

M = 503.69

Monoclinic,

a = 6.5174 (4) Å

b = 13.1221 (8) Å

c = 16.3066 (9) Å

β = 100.194 (1)°

V = 1372.56 (14) Å3

Z = 4

Mo Kα radiation

μ = 7.53 mm−1

T = 100 K

0.18 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.344, T max = 0.398

9918 measured reflections

2464 independent reflections

2149 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.063

S = 1.00

2464 reflections

78 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.87 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014657/cv5413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014657/cv5413Isup2.hkl

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

[SnCl2(C5H4NSe)2]	F(000) = 936
Mr = 503.69	Dx = 2.438 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4192 reflections
a = 6.5174 (4) Å	θ = 2.5–32.4°
b = 13.1221 (8) Å	µ = 7.53 mm−1
c = 16.3066 (9) Å	T = 100 K
β = 100.194 (1)°	Prism, yellow
V = 1372.56 (14) Å3	0.18 × 0.15 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	2464 independent reflections
Radiation source: fine-focus sealed tube	2149 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 32.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.344, Tmax = 0.398	k = −19→19
9918 measured reflections	l = −24→24

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3
2464 reflections	(Δ/σ)max = 0.001
78 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.87 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
Sn1	0.5000	0.622617 (17)	0.2500	0.01852 (6)
Se1	0.16999 (4)	0.584912 (19)	0.140130 (15)	0.02190 (7)
Cl1	0.67676 (9)	0.74412 (5)	0.17723 (4)	0.02544 (12)
N1	0.5494 (3)	0.49464 (16)	0.16204 (12)	0.0204 (4)
C2	0.3618 (4)	0.48906 (18)	0.11081 (14)	0.0209 (4)
C3	0.3249 (4)	0.41919 (19)	0.04601 (16)	0.0237 (5)
H3	0.1933	0.4158	0.0101	0.028*
C4	0.4867 (4)	0.35439 (19)	0.03530 (16)	0.0263 (5)
H4	0.4663	0.3060	−0.0087	0.032*
C5	0.6780 (4)	0.35981 (19)	0.08840 (17)	0.0257 (5)
H5	0.7885	0.3153	0.0814	0.031*
C6	0.7045 (4)	0.4308 (2)	0.15137 (16)	0.0235 (5)
H6	0.8348	0.4350	0.1881	0.028*

	U11	U22	U33	U12	U13	U23
Sn1	0.01985 (11)	0.01864 (11)	0.01647 (10)	0.000	0.00155 (8)	0.000
Se1	0.01990 (12)	0.02333 (13)	0.02113 (12)	0.00098 (8)	−0.00005 (9)	−0.00003 (8)
Cl1	0.0290 (3)	0.0255 (3)	0.0217 (3)	−0.0056 (2)	0.0040 (2)	0.0025 (2)
N1	0.0221 (9)	0.0210 (9)	0.0176 (9)	−0.0009 (7)	0.0018 (7)	0.0003 (7)
C2	0.0218 (10)	0.0201 (10)	0.0203 (10)	−0.0017 (8)	0.0026 (8)	0.0022 (8)
C3	0.0270 (11)	0.0237 (11)	0.0191 (11)	−0.0029 (9)	0.0001 (9)	0.0003 (8)
C4	0.0353 (13)	0.0206 (11)	0.0231 (11)	−0.0035 (9)	0.0055 (10)	−0.0029 (9)
C5	0.0317 (12)	0.0215 (11)	0.0247 (12)	0.0035 (9)	0.0074 (10)	0.0004 (9)
C6	0.0245 (11)	0.0239 (11)	0.0227 (11)	0.0007 (9)	0.0054 (9)	0.0033 (9)

Sn1—N1	2.268 (2)	C3—C4	1.389 (4)
Sn1—Cl1	2.4002 (6)	C3—H3	0.9500
Sn1—Se1	2.5917 (3)	C4—C5	1.388 (4)
Se1—C2	1.893 (2)	C4—H4	0.9500
N1—C6	1.348 (3)	C5—C6	1.375 (4)
N1—C2	1.355 (3)	C5—H5	0.9500
C2—C3	1.388 (3)	C6—H6	0.9500
N1—Sn1—N1i	84.47 (10)	N1—C2—Se1	111.86 (17)
N1—Sn1—Cl1	92.57 (5)	C3—C2—Se1	126.74 (19)
N1i—Sn1—Cl1	159.83 (5)	C2—C3—C4	117.9 (2)
Cl1—Sn1—Cl1i	96.75 (3)	C2—C3—H3	121.1
N1—Sn1—Se1	67.34 (5)	C4—C3—H3	121.1
N1i—Sn1—Se1	95.89 (5)	C5—C4—C3	120.5 (2)
Cl1—Sn1—Se1	101.376 (16)	C5—C4—H4	119.7
Cl1i—Sn1—Se1	93.231 (16)	C3—C4—H4	119.7
N1—Sn1—Se1i	95.89 (5)	C6—C5—C4	118.8 (2)
Se1—Sn1—Se1i	157.988 (15)	C6—C5—H5	120.6
C2—Se1—Sn1	78.30 (7)	C4—C5—H5	120.6
C6—N1—C2	120.2 (2)	N1—C6—C5	121.3 (2)
C6—N1—Sn1	137.34 (17)	N1—C6—H6	119.4
C2—N1—Sn1	102.49 (15)	C5—C6—H6	119.4
N1—C2—C3	121.4 (2)
N1—Sn1—Se1—C2	−0.40 (9)	Se1i—Sn1—N1—C2	165.79 (14)
N1i—Sn1—Se1—C2	−81.89 (9)	C6—N1—C2—C3	−0.8 (3)
Cl1—Sn1—Se1—C2	87.63 (7)	Sn1—N1—C2—C3	179.55 (19)
Cl1i—Sn1—Se1—C2	−174.81 (7)	C6—N1—C2—Se1	178.91 (17)
Se1i—Sn1—Se1—C2	−43.00 (7)	Sn1—N1—C2—Se1	−0.77 (17)
N1i—Sn1—N1—C6	−80.3 (2)	Sn1—Se1—C2—N1	0.67 (15)
Cl1—Sn1—N1—C6	79.7 (2)	Sn1—Se1—C2—C3	−179.7 (2)
Cl1i—Sn1—N1—C6	−162.64 (17)	N1—C2—C3—C4	0.3 (4)
Se1—Sn1—N1—C6	−179.0 (3)	Se1—C2—C3—C4	−179.38 (18)
Se1i—Sn1—N1—C6	−13.8 (2)	C2—C3—C4—C5	0.3 (4)
N1i—Sn1—N1—C2	99.31 (15)	C3—C4—C5—C6	−0.4 (4)
Cl1—Sn1—N1—C2	−100.69 (14)	C2—N1—C6—C5	0.7 (4)
Cl1i—Sn1—N1—C2	16.9 (3)	Sn1—N1—C6—C5	−179.76 (18)
Se1—Sn1—N1—C2	0.56 (12)	C4—C5—C6—N1	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1ii	0.95	2.82	3.675 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1i	0.95	2.82	3.675 (3)	151

Symmetry code: (i) .