[Bis(pyridin-2-yl) selenide-κ2N,N′]tetra­chloridotin(IV)

Mammadova, G.Z.; Matsulevich, Z.V.; Osmanov, V.K.; Borisov, A.V.; Khrustalev, V.N.

doi:10.1107/S160053681202586X

metal-organic compounds

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Volume 68| Part 7| July 2012| Page m983

https://doi.org/10.1107/S160053681202586X

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[Bis(pyridin-2-yl) selenide-κ²N,N′]tetrachloridotin(IV)

Gunay Z. Mammadova,^a ^* Zhanna V. Matsulevich,^b Vladimir K. Osmanov,^b Alexander V. Borisov ^b and Victor N. Khrustalev ^c

^aBaku State University, Z. Khalilov St 23, Baku, AZ-1148, Azerbaijan, ^bR.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St, Nizhny Novgorod, 603950, Russian Federation, and ^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: gunka479@mail.ru

(Received 4 June 2012; accepted 7 June 2012; online 30 June 2012)

The title compound, [SnCl₄(C₁₀H₈N₂Se)], was obtained by the reaction of 2,2′-dipyridyl diselenide with tin tetrachloride. The Sn^IV ion is coordinated by two N atoms [Sn—N = 2.266 (2) and 2.274 (2) Å] from the bis(2-pyridyl)selenide ligand and four chloride anions [Sn—Cl = 2.3717 (6)–2.3939 (6) Å] in a distorted octahedral 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 intermolecular Se⋯Cl contacts [3.5417 (7) and 3.5648 (7) Å], weak C—H⋯Cl hydrogen bonds and π–π stacking interactions 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_r = 495.63
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.058
S = 1.00
4096 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 1.64 e Å⁻³
Δρ_min = −1.10 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202586X/cv5309sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202586X/cv5309Isup2.hkl

checkCIF report

Comment top

2,2'-Dipyridyl sulfide plays prominent role as useful ligand in coordination chemistry (Tresoldi et al., 1992; Kondo et al., 1995; Blake et al., 2002; Teles et al., 2006; Zhao et al., 2007; Wriedt et al., 2008a, 2008b, 2008c). The important structural feature of these complexes is the practically unchangeable bond angle at sulfur atom. On the other hand, the most labile geometrical parameters in them are the dihedral angle between two pyridine rings as well as the deviation of metal atom from the mean plane of the central six-membered chelate ring passed through the two nitrogen and two carbon atoms due to the different coordination environment. It is interesting to note that 2,2'-dipyridyl selenide is also known (Dunne et al., 1995), however, no structurally characterized metal complexes with this ligand were reported till now.

This article is dedicated to the first structural characterization of metal complex with 2,2'-dipyridyl selenide ligand - [bis(2-pyridyl)selenide-k²N,N')]tetrachlorido-tin(IV), C₁₀H₈Cl₄N₂SeSn (I), which was obtained by the reaction of 2,2'-dipyridyl diselenide with tin tetrachloride (Figure 1).

The molecule of I possesses overall intrinsic C_s (m) symmetry (Figure 2). The tin ion is coordinated by two N atoms [Sn—N 2.266 (2), 2.274 (2) Å] from bis(2-pyridyl)selenide ligand and four chloride anions [Sn—Cl 2.3717 (6)–2.3939 (6) Å] in a distorted octahedral geometry. The central six-membered chelate ring has a boat conformation with the Se and Sn atoms deviating from the mean plane passed through the rest four atoms of the ring at 0.692 (3) and 0.855 (3) Å, respectively. Two pyridine rings are inclined to each other with a dihedral angle of 49.62 (8)°. Remarkably, the value of the bond angle at selenium atom in I (101.51 (10)°) is almost equal to that in the free 2,2'-dipyridyl selenide ligand (101.9 (2)°) (Dunne et al., 1995).

In the crystal, the molecules of I form the chains along the a axis by the attractive intermolecular Se1···Cl2ⁱ [3.5417 (7) Å] and Se1···Cl4ⁱ [3.5648 (7) Å] interactions. The chains are further linked into a three-dimensional framework by weak C—H···Cl hydrogen bonds (Table 1) and π···π stacking interactions between the pyridine rings with a centroid-centroid distance of 3.683 (3) Å. Symmetry code: (i) x - 1, y, z.

Related literature top

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 top

A solution of SnCl₄ (0.13 g, 0.5 mmol) in CH₂Cl₂ (25 ml) was added to a solution of 2,2'-dipyridyl diselenide (0.16 g, 0.5 mmol) in CH₂Cl₂ (25 ml) with stirring at room temperature. After 10 min, solvent was evaporated in vacuo. An attempt to re-crystallization of the solid residue from CH₃CN led to formation of the powder Se which was separated by filtration of hot solution. The filtrate was concentrated in vacuo. The solid was re-crystallized from CH₃CN to give I as yellow crystals. Yield is 82%. M.p. = 541–543 K. ¹H NMR (DMSO-d₆, 300 MHz, 302 K): δ = 8.48 (d, 2H, J = 4.8), 7.70 (t, 2H, J = 7.8), 7.55 (d, 2H, J = 7.8), 7.28 (dd, 2H, J = 7.8, J = 4.8). Anal. Calcd for C₁₀H₈Cl₄N₂SeSn: C, 24.23; H, 1.63; N, 5.65. Found: C, 24.14;H, 1.59; N, 5.57.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction of 2,2'-dipyridyl diselenide with tin tetrachloride.
	Fig. 2. The molecular structure of I showing the atomic numbering and 50% probability displacement ellipsoids.

[Bis(pyridin-2-yl) selenide-κ²N,N']tetrachloridotin(IV) top

Crystal data top

[SnCl₄(C₁₀H₈N₂Se)]	F(000) = 936
M_r = 495.63	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.018P)² + 5.2P] where P = (F_o² + 2F_c²)/3
4096 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 1.64 e Å⁻³
0 restraints	Δρ_min = −1.10 e Å⁻³

Crystal data top

[SnCl₄(C₁₀H₈N₂Se)]	V = 1401.65 (11) Å³
M_r = 495.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0835 (4) Å	µ = 5.16 mm⁻¹
b = 12.2153 (5) Å	T = 100 K
c = 14.4710 (6) Å	0.30 × 0.24 × 0.15 mm
β = 101.208 (1)°

Data collection top

Bruker SMART 1K CCD diffractometer	4096 independent reflections
Absorption correction: multi-scan [SADABS; Sheldrick, 1998)	3723 reflections with I > 2σ(I)
T_min = 0.306, T_max = 0.511	R_int = 0.026
16245 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.00	Δρ_max = 1.64 e Å⁻³
4096 reflections	Δρ_min = −1.10 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[SnCl₄(C₁₀H₈N₂Se)]
M_r	495.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.0835 (4), 12.2153 (5), 14.4710 (6)
β (°)	101.208 (1)
V (Å³)	1401.65 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.16
Crystal size (mm)	0.30 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART 1K CCD
Absorption correction	Multi-scan [SADABS; Sheldrick, 1998)
T_min, T_max	0.306, 0.511
No. of measured, independent and observed [I > 2σ(I)] reflections	16245, 4096, 3723
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.058, 1.00
No. of reflections	4096
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.64, −1.10

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) x−1, −y+3/2, z−1/2.

Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help in this work.

References

Blake, A. J., George, M. W., Hubberstey, P., Garcia, R. L. & Wilson, C. (2002). Acta Cryst. E58, m96–m98. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dunne, S. J., von Nagy-Felsobuki, E. I. & Mackay, M. F. (1995). Acta Cryst. C51, 1454–1457. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kondo, M., Kawata, S., Kitagawa, S., Kiso, H. & Munakata, M. (1995). Acta Cryst. C51, 567–569. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Teles, W. M., Marinho, M. V., Yoshida, M. I., Speziali, N. L., Krambrock, K., Pinheiro, C. B., Pinhal, N. M., Leitão, A. A. & Machado, F. C. (2006). Inorg. Chim. Acta, 359, 4613–4618. Web of Science CSD CrossRef CAS Google Scholar
Tresoldi, G., Rotondo, E., Piraino, P., Lanfranchi, M. & Tiripicchio, A. (1992). Inorg. Chim. Acta, 194, 233–241. CSD CrossRef CAS Web of Science Google Scholar
Wriedt, M., Jess, I. & Näther, C. (2008a). Acta Cryst. E64, m10. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wriedt, M., Jess, I. & Näther, C. (2008b). Acta Cryst. E64, m11. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wriedt, M., Jess, I. & Näther, C. (2008c). Acta Cryst. E64, m315. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, Q.-H., Mu, X.-M. & Fang, R.-B. (2007). Pol. J. Chem. 81, 1369–1373. CAS Google Scholar