[Bis(pyridin-2-yl) selenide-κ(2)N,N']tetra-chloridotin(IV).

The title compound, [SnCl(4)(C(10)H(8)N(2)Se)], was obtained by the reaction of 2,2'-dipyridyl diselenide with tin tetra-chloride. The Sn(IV) ion is coordinated by two N atoms [Sn-N = 2.266 (2) and 2.274 (2) Å] from the bis-(2-pyrid-yl)selenide ligand and four chloride anions [Sn-Cl = 2.3717 (6)-2.3939 (6) Å] in a distorted octa-hedral geometry. The central six-membered chelate ring has a boat conformation with the Se and Sn atoms deviating by 0.692 (3) and 0.855 (3) Å, respectively, from the mean plane through the remaining four ring atoms. The pyridine rings are inclined to each other by a dihedral angle of 49.62 (8)°. The crystal packing exhibits short inter-molecular Se⋯Cl contacts [3.5417 (7) and 3.5648 (7) Å], weak C-H⋯Cl hydrogen bonds and π-π stacking inter-actions between the pyridine rings with a centroid-centroid distance of 3.683 (3) Å.

Related literature

For the crystal structure of the 2,2′-dipyridyl-selenide ligand, see: Dunne et al. (1995 ▶). For the crystal structures of related compounds, see: Tresoldi et al. (1992 ▶); Kondo et al. (1995 ▶); Blake et al. (2002 ▶); Teles et al. (2006 ▶); Zhao et al. (2007 ▶); Wriedt et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

[SnCl4(C10H8N2Se)]

M = 495.63

Monoclinic,

a = 8.0835 (4) Å

b = 12.2153 (5) Å

c = 14.4710 (6) Å

β = 101.208 (1)°

V = 1401.65 (11) Å3

Z = 4

Mo Kα radiation

μ = 5.16 mm−1

T = 100 K

0.30 × 0.24 × 0.15 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan [SADABS; Sheldrick, 1998 ▶) T min = 0.306, T max = 0.511

16245 measured reflections

4096 independent reflections

3723 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.058

S = 1.00

4096 reflections

163 parameters

H-atom parameters constrained

Δρmax = 1.64 e Å−3

Δρmin = −1.10 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: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202586X/cv5309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202586X/cv5309Isup2.hkl

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

[SnCl4(C10H8N2Se)]	F(000) = 936
Mr = 495.63	Dx = 2.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9615 reflections
a = 8.0835 (4) Å	θ = 2.2–30.0°
b = 12.2153 (5) Å	µ = 5.16 mm−1
c = 14.4710 (6) Å	T = 100 K
β = 101.208 (1)°	Prism, yellow
V = 1401.65 (11) Å3	0.30 × 0.24 × 0.15 mm
Z = 4

Bruker SMART 1K CCD diffractometer	4096 independent reflections
Radiation source: fine-focus sealed tube	3723 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan [SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.306, Tmax = 0.511	k = −17→17
16245 measured reflections	l = −20→20

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.018P)2 + 5.2P] where P = (Fo2 + 2Fc2)/3
4096 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 1.64 e Å−3
0 restraints	Δρmin = −1.10 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	0.381830 (19)	0.755376 (12)	0.120929 (11)	0.01034 (5)
Se1	−0.08948 (3)	0.76213 (2)	0.108418 (18)	0.01534 (6)
Cl1	0.46143 (7)	0.84715 (5)	−0.00939 (4)	0.01648 (11)
Cl2	0.59551 (7)	0.84559 (5)	0.23278 (4)	0.01729 (11)
Cl3	0.27580 (8)	0.67096 (5)	0.24510 (4)	0.01741 (11)
Cl4	0.54619 (7)	0.59645 (5)	0.10454 (4)	0.01745 (11)
N1	0.2061 (3)	0.89921 (17)	0.12452 (14)	0.0129 (4)
N2	0.1674 (3)	0.68416 (17)	0.01238 (14)	0.0131 (4)
C1	0.0371 (3)	0.8955 (2)	0.11795 (17)	0.0145 (4)
C2	−0.0569 (3)	0.9903 (2)	0.12213 (18)	0.0177 (5)
H2	−0.1758	0.9862	0.1167	0.021*
C3	0.0241 (3)	1.0905 (2)	0.13423 (18)	0.0182 (5)
H3	−0.0382	1.1556	0.1387	0.022*
C4	0.1969 (3)	1.0950 (2)	0.13974 (18)	0.0184 (5)
H4	0.2551	1.1629	0.1477	0.022*
C5	0.2831 (3)	0.9981 (2)	0.13332 (17)	0.0156 (4)
H5	0.4011	1.0012	0.1352	0.019*
C6	0.0019 (3)	0.68436 (19)	0.01536 (17)	0.0134 (4)
C7	−0.1159 (3)	0.6267 (2)	−0.04941 (18)	0.0167 (5)
H7	−0.2316	0.6271	−0.0450	0.020*
C8	−0.0625 (3)	0.5688 (2)	−0.12034 (18)	0.0187 (5)
H8	−0.1401	0.5266	−0.1639	0.022*
C9	0.1063 (3)	0.5734 (2)	−0.12678 (17)	0.0176 (5)
H9	0.1451	0.5369	−0.1765	0.021*
C10	0.2175 (3)	0.6317 (2)	−0.06004 (17)	0.0153 (4)
H10	0.3328	0.6351	−0.0651	0.018*

	U11	U22	U33	U12	U13	U23
Sn1	0.00923 (7)	0.01100 (8)	0.01039 (8)	0.00012 (5)	0.00091 (5)	−0.00026 (5)
Se1	0.01033 (11)	0.01823 (12)	0.01802 (12)	−0.00126 (8)	0.00412 (9)	−0.00212 (9)
Cl1	0.0171 (3)	0.0176 (3)	0.0157 (3)	−0.0012 (2)	0.0055 (2)	0.0024 (2)
Cl2	0.0152 (2)	0.0166 (3)	0.0178 (3)	−0.0017 (2)	−0.0023 (2)	−0.0027 (2)
Cl3	0.0206 (3)	0.0184 (3)	0.0138 (2)	−0.0021 (2)	0.0049 (2)	0.0021 (2)
Cl4	0.0161 (3)	0.0151 (3)	0.0203 (3)	0.0045 (2)	0.0014 (2)	−0.0015 (2)
N1	0.0133 (9)	0.0124 (9)	0.0131 (9)	0.0010 (7)	0.0025 (7)	0.0002 (7)
N2	0.0120 (9)	0.0135 (9)	0.0132 (9)	0.0004 (7)	0.0012 (7)	−0.0006 (7)
C1	0.0154 (10)	0.0161 (11)	0.0120 (10)	0.0006 (8)	0.0028 (8)	0.0000 (8)
C2	0.0177 (11)	0.0197 (12)	0.0168 (11)	0.0035 (9)	0.0058 (9)	0.0009 (9)
C3	0.0261 (13)	0.0138 (11)	0.0165 (11)	0.0055 (9)	0.0087 (10)	0.0033 (9)
C4	0.0250 (13)	0.0122 (10)	0.0184 (11)	0.0015 (9)	0.0053 (10)	−0.0007 (9)
C5	0.0160 (11)	0.0142 (10)	0.0169 (11)	0.0004 (8)	0.0038 (9)	0.0016 (9)
C6	0.0130 (10)	0.0112 (10)	0.0157 (11)	0.0003 (8)	0.0018 (8)	0.0012 (8)
C7	0.0138 (10)	0.0155 (11)	0.0187 (11)	−0.0013 (8)	−0.0018 (9)	0.0017 (9)
C8	0.0206 (12)	0.0142 (11)	0.0174 (11)	0.0022 (9)	−0.0061 (9)	0.0004 (9)
C9	0.0226 (12)	0.0159 (11)	0.0127 (11)	0.0031 (9)	−0.0007 (9)	−0.0016 (8)
C10	0.0154 (10)	0.0166 (11)	0.0138 (10)	0.0030 (8)	0.0024 (8)	−0.0021 (8)

Sn1—N1	2.266 (2)	C2—H2	0.9500
Sn1—N2	2.274 (2)	C3—C4	1.385 (4)
Sn1—Cl3	2.3717 (6)	C3—H3	0.9500
Sn1—Cl1	2.3873 (6)	C4—C5	1.385 (3)
Sn1—Cl4	2.3901 (6)	C4—H4	0.9500
Sn1—Cl2	2.3939 (6)	C5—H5	0.9500
Se1—C6	1.910 (2)	C6—C7	1.391 (3)
Se1—C1	1.914 (2)	C7—C8	1.383 (4)
N1—C1	1.351 (3)	C7—H7	0.9500
N1—C5	1.353 (3)	C8—C9	1.387 (4)
N2—C6	1.347 (3)	C8—H8	0.9500
N2—C10	1.356 (3)	C9—C10	1.382 (3)
C1—C2	1.393 (3)	C9—H9	0.9500
C2—C3	1.383 (4)	C10—H10	0.9500
N1—Sn1—N2	85.14 (7)	C3—C2—H2	120.2
N1—Sn1—Cl3	89.95 (5)	C1—C2—H2	120.2
N2—Sn1—Cl3	91.02 (5)	C2—C3—C4	119.3 (2)
N1—Sn1—Cl1	85.44 (5)	C2—C3—H3	120.4
N2—Sn1—Cl1	85.43 (5)	C4—C3—H3	120.4
Cl3—Sn1—Cl1	174.40 (2)	C3—C4—C5	118.5 (2)
N1—Sn1—Cl4	174.23 (5)	C3—C4—H4	120.7
N2—Sn1—Cl4	89.11 (5)	C5—C4—H4	120.7
Cl3—Sn1—Cl4	90.68 (2)	N1—C5—C4	122.7 (2)
Cl1—Sn1—Cl4	93.59 (2)	N1—C5—H5	118.6
N1—Sn1—Cl2	90.05 (5)	C4—C5—H5	118.6
N2—Sn1—Cl2	174.98 (5)	N2—C6—C7	122.1 (2)
Cl3—Sn1—Cl2	90.42 (2)	N2—C6—Se1	123.11 (18)
Cl1—Sn1—Cl2	92.76 (2)	C7—C6—Se1	114.76 (18)
Cl4—Sn1—Cl2	95.68 (2)	C8—C7—C6	119.2 (2)
C6—Se1—C1	101.51 (10)	C8—C7—H7	120.4
C1—N1—C5	118.5 (2)	C6—C7—H7	120.4
C1—N1—Sn1	127.01 (16)	C7—C8—C9	118.8 (2)
C5—N1—Sn1	114.52 (16)	C7—C8—H8	120.6
C6—N2—C10	118.3 (2)	C9—C8—H8	120.6
C6—N2—Sn1	127.28 (16)	C10—C9—C8	119.2 (2)
C10—N2—Sn1	114.38 (16)	C10—C9—H9	120.4
N1—C1—C2	121.4 (2)	C8—C9—H9	120.4
N1—C1—Se1	123.52 (18)	N2—C10—C9	122.2 (2)
C2—C1—Se1	114.99 (18)	N2—C10—H10	118.9
C3—C2—C1	119.5 (2)	C9—C10—H10	118.9
N2—Sn1—N1—C1	37.1 (2)	C6—Se1—C1—C2	136.94 (19)
Cl3—Sn1—N1—C1	−53.95 (19)	N1—C1—C2—C3	−0.7 (4)
Cl1—Sn1—N1—C1	122.9 (2)	Se1—C1—C2—C3	176.52 (19)
Cl2—Sn1—N1—C1	−144.38 (19)	C1—C2—C3—C4	1.5 (4)
N2—Sn1—N1—C5	−142.22 (17)	C2—C3—C4—C5	−0.3 (4)
Cl3—Sn1—N1—C5	126.76 (17)	C1—N1—C5—C4	2.7 (4)
Cl1—Sn1—N1—C5	−56.43 (16)	Sn1—N1—C5—C4	−177.9 (2)
Cl2—Sn1—N1—C5	36.33 (17)	C3—C4—C5—N1	−1.9 (4)
N1—Sn1—N2—C6	−42.8 (2)	C10—N2—C6—C7	4.4 (3)
Cl3—Sn1—N2—C6	47.1 (2)	Sn1—N2—C6—C7	−172.03 (18)
Cl1—Sn1—N2—C6	−128.6 (2)	C10—N2—C6—Se1	−176.05 (18)
Cl4—Sn1—N2—C6	137.7 (2)	Sn1—N2—C6—Se1	7.5 (3)
N1—Sn1—N2—C10	140.65 (18)	C1—Se1—C6—N2	40.4 (2)
Cl3—Sn1—N2—C10	−129.48 (17)	C1—Se1—C6—C7	−140.06 (19)
Cl1—Sn1—N2—C10	54.85 (17)	N2—C6—C7—C8	−1.2 (4)
Cl4—Sn1—N2—C10	−38.82 (17)	Se1—C6—C7—C8	179.23 (19)
C5—N1—C1—C2	−1.4 (4)	C6—C7—C8—C9	−2.4 (4)
Sn1—N1—C1—C2	179.31 (17)	C7—C8—C9—C10	2.7 (4)
C5—N1—C1—Se1	−178.36 (18)	C6—N2—C10—C9	−4.1 (4)
Sn1—N1—C1—Se1	2.4 (3)	Sn1—N2—C10—C9	172.81 (19)
C6—Se1—C1—N1	−45.9 (2)	C8—C9—C10—N2	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl3i	0.95	2.79	3.3965 (18)	122
C8—H8···Cl2ii	0.95	2.83	3.3126 (18)	113
C8—H8···Cl3iii	0.95	2.81	3.6870 (19)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl3i	0.95	2.79	3.3965 (18)	122
C8—H8⋯Cl2ii	0.95	2.83	3.3126 (18)	113

Symmetry codes: (i) ; (ii) .