research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

trans-Di­chlorido­bis­­(di­methyl sulfoxide-κO)bis­­(4-fluoro­benzyl-κC1)tin(IV): crystal structure and Hirshfeld surface analysis

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, bResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, cDepartment of Chemistry, Lancaster University, Lancaster LA1 4YB, United Kingdom, and dDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India
*Correspondence e-mail: edwardt@sunway.edu.my

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 March 2017; accepted 2 April 2017; online 7 April 2017)

The SnIV atom in the title diorganotin compound, [Sn(C7H6F)2Cl2(C2H6OS)2], is located on a centre of inversion, resulting in the C2Cl2O2 donor set having an all-trans disposition of like atoms. The coordination geometry approximates an octa­hedron. The crystal features C—H⋯F, C—H⋯Cl and C—H⋯π inter­actions, giving rise to a three-dimensional network. The respective influences of the Cl⋯H/H⋯Cl and F⋯H/H⋯F contacts to the mol­ecular packing are clearly evident from the analysis of the Hirshfeld surface.

1. Chemical context

The structural chemistry of organotin(IV) compounds with multidentate Schiff base ligands has been of inter­est since the observation of the diversity in their supra­molecular association patterns (Teoh et al., 1997[Teoh, S.-G., Yeap, G.-Y., Loh, C.-C., Foong, L.-W., Teo, S.-B. & Fun, H.-K. (1997). Polyhedron, 16, 2213-2221.]; Dey et al., 1999[Dey, D. K., Dasa, M. K. & Nöth, H. (1999). Z. Naturforsch. Teil B, 54, 145-154.]). Typically, these multidentate ligands bind to the tin atom through the phenolic-O, imine-N, oxime-O or even oxime-N atoms. In view of this, the coordination of these multidentate ligands to (organo)tin may lead to more thermodynamically stable organotin complexes, in contrast to those with monodentate ligands (Vallet et al., 2003[Vallet, V., Wahlgren, U. & Grenthe, I. (2003). J. Am. Chem. Soc. 125, 14941-14950.]; Contreras et al., 2009[Contreras, R., Flores-Parra, A., Mijangos, E., Téllez, F., López-Sandoval, H. & Barba-Behrens, N. (2009). Coord. Chem. Rev. 253, 1979-1999.]), a feature which could potentially be useful in catalytic studies (Yearwood et al., 2002[Yearwood, B., Parkin, S. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124-131.]). In consideration of this and as part of on-going work with multidentate ligands of organotin compounds (Lee et al., 2004[Lee, S. M., Lo, K. M. & Ng, S. W. (2004). Acta Cryst. E60, m1614-m1616.]), an attempt to synthesize an adduct of the potentially tetra­dentate Schiff base N,N-1,1,2,2-di­nitrile­vinyl­enebis(5-bromo­salicylaldiminato) with di(p-fluoro­benz­yl)tin(IV) dichloride was made.

[Scheme 1]

The complex was obtained as an orange powder and was successfully characterized using various spectroscopic methods including 1H NMR spectroscopy. Upon inter­action with DMSO-d6, in the context of NMR studies, colourless crystals were obtained after several weeks standing. The formation of the new title compound, (I)[link], is likely due to degradation of the complex while stored in the NMR tube. In the present contribution, the crystal and mol­ecular structures of (I)[link] are described as well as a detailed analysis of the inter­molecular association through a Hirshfeld surface analysis.

2. Structural commentary

The mol­ecular structure of (I)[link], Fig. 1[link], has the SnIV atom situated on a crystallographic centre of inversion. The SnIV atom is coordinated by monodentate ligands, i.e. chloride, sulfoxide-O and methyl­ene-C atoms. From symmetry, each donor is trans to a like atom resulting in an all-trans-C2Cl2O2 donor set about the SnIV atom. The donor set defines a distorted octa­hedral geometry owing, in part, to the disparate Sn—donor atom bond lengths, Table 1[link]. The angles about the SnIV atom differ relatively little from the ideal octa­hedral angles with the maximum deviation of ca 6° noted for the C1—Sn—O1 angle, Table 1[link].

Table 1
Selected geometric parameters (Å, °)

Sn—C1 2.1628 (16) Sn—Cl1 2.5599 (4)
Sn—O1 2.2332 (11)    
       
C1—Sn—O1 95.99 (5) C1—Sn—Cl1i 89.95 (5)
C1—Sn—Cl1 90.05 (5) O1—Sn—Cl1 90.44 (3)
C1—Sn—O1i 84.01 (5) O1—Sn—Cl1i 89.56 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.
[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. The SnIV atom lies on a centre of inversion; unlabelled atoms are related by the symmetry operation 1 − x, 1 − y, 1 − z.

3. Supra­molecular features

The mol­ecular packing in (I)[link] comprises C—H⋯F, C—H⋯Cl and C—H⋯π inter­actions which combine to generate a three-dimensional network, Table 2[link]. The chloride atom participates in phenyl-C6—H⋯Cl1 and methyl-C8—H⋯Cl1 inter­actions. As each chloride atom is involved in two C—H⋯Cl inter­actions and there are two chloride atoms per mol­ecule, the C—H⋯Cl inter­actions extend laterally to give rise to a supra­molecular layer in the bc plane, Fig. 2[link]a. Layers are connected along the a axis by phenyl-C3—H⋯F1 and methyl-C9—H⋯π(phen­yl) inter­actions to consolidate the mol­ecular packing, Fig. 2[link]b.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯F1ii 0.95 2.49 3.333 (2) 147
C6—H6⋯Cl1iii 0.95 2.77 3.6129 (18) 148
C8—H8B⋯Cl1iv 0.98 2.76 3.6379 (17) 150
C9—H9CCg1v 0.98 2.67 3.3887 (19) 130
Symmetry codes: (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x+1, y, z.
[Figure 2]
Figure 2
The mol­ecular packing in (I)[link]: (a) supra­molecular layer in the bc plane sustained by C—H⋯Cl inter­actions and (b) a view of the unit-cell contents in projection down the c axis. The C—H⋯Cl, C—H⋯F and C—H⋯π inter­actions are shown as orange, blue and purple dashed lines, respectively.

4. Hirshfeld surface analysis

The Hirshfeld surface analysis on the structure of (I)[link] provides more insight into the mol­ecular packing and was performed as described recently (Wardell et al., 2016[Wardell, J. L., Jotani, M. M. & Tiekink, E. R. T. (2016). Acta Cryst. E72, 1618-1627.]). It is evident from the bright-red spots appearing near the chloride and fluoride atoms on the Hirshfeld surface mapped over dnorm in Fig. 3[link] that these atoms play a significant role in the mol­ecular packing. Thus, the bright-red spots near phenyl-H6, methyl-H8B and a pair near Cl1 in Fig. 3[link] indicate the presence of bifurcated C—H⋯Cl inter­actions formed by each of the chloride atoms. Similarly, the pair of red spots near phenyl-H3 and F1 atoms are associated with the donor and acceptor of C—H⋯F inter­actions, respectively. The donors and acceptors of C—H⋯Cl and C—H⋯F inter­actions are also represented with blue (positive potential) and red regions (negative potential), respectively, on the Hirshfeld surface mapped over the electrostatic potential in Fig. 4[link]. In addition to above, the Cl1 and F1 atoms also participate in short inter­atomic contacts with methyl-H atoms, Table 3[link]. The presence of faint-red spots near the phenyl-C4 and methyl-C9 atoms in Fig. 3[link] indicate their participation in a short inter­atomic C⋯C contact, Table 3[link], which compliments the methyl-C—H⋯π(phen­yl) contact described above. The presence of the C—H⋯π inter­action is also evident from the view of Hirshfeld surface mapped over the electrostatic potential around participating atoms, Fig. 4[link]; the donors and acceptors of these inter­actions are viewed as the convex surface around atoms of the methyl-C9 groups and the concave surface above the (C2–C7) phenyl ring, respectively. The immediate environments about a reference mol­ecule within dnorm- and shape-index-mapped Hirshfeld surfaces highlighting the various C—H⋯Cl, C—H⋯F and C—H⋯π inter­actions are illustrated in Fig. 5[link]ac, respectively.

Table 3
Summary of short inter­atomic contacts (Å) in (I)

Contact distance symmetry operation
C4⋯C9 3.371 (2) −1 + x, y, z
F1⋯H8A 2.66 1 − x, −y, 1 − z
Cl1⋯H9B 2.91 1 − x, [{1\over 2}] + y, [{1\over 2}] − z
Note: (a) the SnIV atom is located on a centre of inversion.
[Figure 3]
Figure 3
A view of the Hirshfeld surface for (I)[link] mapped over dnorm over the range −0.049 to 1.356 au.
[Figure 4]
Figure 4
A view of the Hirshfeld surface for (I)[link] mapped over the electrostatic potential in the range ±0.095 au.
[Figure 5]
Figure 5
Views of the Hirshfeld surfaces about a reference mol­ecule mapped over (a) shape-index, (b) dnorm and (c) shape-index, highlighting (a) C—H⋯F and short inter­atomic F⋯H/H⋯F contacts as black and red dashed lines, respectively, (b) C—H⋯Cl and short inter­atomic Cl⋯H/H⋯Cl contacts as black and red dashed lines, respectively, and (c) C—H⋯π and short inter­atomic C⋯C contacts as white and red dashed lines, respectively.

The overall two-dimensional fingerprint plot and those delineated into H⋯H, Cl⋯H/H⋯Cl, F⋯H/H⋯F, C⋯H/H⋯C and O⋯H/H⋯O contacts (McKinnon et al., 2007[McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814-3816.]) are illustrated in Fig. 6[link]af, respectively, and their relative contributions to the Hirshfeld surfaces are summarized in Table 4[link]. It is clear from the fingerprint plot delineated into H⋯H contacts, Fig. 6[link]b, that although these contacts have the greatest contribution, i.e. 45.7%, to the Hirshfeld surface, the dispersion forces acting between them keep these atoms at the distances greater than the sum of their van der Waals radii, hence they do not contribute significantly to the mol­ecular packing. The comparatively greater contribution of F⋯H/H⋯F contacts to the Hirshfeld surface cf. Cl⋯H/H⋯Cl contacts, Table 4[link], is due to the relative positions of the chloride and fluoride atoms in the mol­ecule, the fluoride atoms being at the extremities and the chloride atoms near the tin(IV) atom. However, the Cl⋯H/H⋯Cl contacts have a greater influence on the mol­ecular packing as viewed from the delineated fingerprint plot in Fig. 6[link]c. The forceps-like distribution of points in the plot with tips at de + di ∼2.8 Å result from the bifurcated C—H⋯Cl inter­actions, and points at positions less than the sum of their van der Waals radii are ascribed to the short inter­atomic Cl⋯H/H⋯Cl contacts, the green appearance due to high density of inter­actions. Similarly, a pair of short spikes at de + di ∼2.5 Å in the fingerprint plot delineated into F⋯H/H⋯F contacts, Fig. 6[link]d, are indicative of inter­molecular C—H⋯F inter­actions with the short inter­atomic F⋯H/H⋯F contacts merged within the fingerprint plot. It is important to note from the fingerprint plot delineated into C⋯H/H⋯C contacts, Fig. 6[link]e, that even though their inter­atomic distances are equal to or greater than the sum of their van der Waals radii, i.e. 2.9 Å, the 12.8% contribution from these to the Hirshfeld surfaces are indicative of the presence of C—H⋯π inter­actions in the structure. This is also justified from the presence of short inter­atomic C⋯C contacts, Fig. 5[link]c and Table 3[link]. The 4.1% contribution from O⋯H/H⋯O contributions to Hirshfeld surfaces, Fig. 6[link]f, and the small contributions from the other contacts listed in Table 2[link] have a negligible effect on the packing.

Table 4
Percentage contribution of inter­atomic contacts to the Hirshfeld surface for (I)

Contact percentage contribution
H⋯H 45.7
Cl⋯H/H⋯Cl 15.1
F⋯H/H⋯F 19.8
C⋯H/H⋯C 12.8
O⋯H/H⋯O 4.1
S⋯H/H⋯S 1.7
Cl⋯F/F⋯Cl 0.6
C⋯Cl/Cl⋯C 0.1
F⋯F 0.1
[Figure 6]
Figure 6
Fingerprint plots for (I)[link]: (a) overall and those delineated into (b) H⋯H, (c) Cl⋯H/H⋯Cl, (d) F⋯H/H⋯F, (e) C⋯H/H⋯C and (f) O⋯H/H⋯O contacts.

5. Database survey

There are three related structures of the general formula R2SnX2(DMSO)2 in the crystallographic literature (Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]). Key bond angles for these are listed in Table 5[link]. The Me2SnBr2(DMSO)2 compound (Aslanov et al., 1978[Aslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S. (1978). Zh. Strukt. Khim. 19, 109-115.]) is analogous to (I)[link] in that the SnIV atom is located on a centre of inversion and hence, is an all-trans isomer. The two remaining structures have a different arrangements of donor atoms with the common feature being the trans-disposition of the Sn-bound organic groups, with the halides and DMSO-O atoms being mutually cis, i.e. R = Me and X = Cl (Aslanov et al., 1978[Aslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S. (1978). Zh. Strukt. Khim. 19, 109-115.]; Isaacs & Kennard, 1970[Isaacs, N. W. & Kennard, C. H. L. (1970). J. Chem. Soc. A, pp. 1257-1261.]) and R = Ph and X = Cl (Sadiq-ur-Rehman et al., 2007[Sadiq-ur-Rehman, Saeed, S., Ali, S., Shahzadi, S. & Helliwell, M. (2007). Acta Cryst. E63, m1788.]). Clearly, further studies are required to ascertain the factor(s) determining the adoption of one coordination geometry over another.

Table 5
Selected geometric parameters (Å, °) for mol­ecules of the general formula R2SnX2(DMSO)2

Compound X—Sn—X O—Sn—O C—Sn—C Reference
Me2SnBr2(DMSO)2 180 180 180 Aslanov et al. (1978[Aslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S. (1978). Zh. Strukt. Khim. 19, 109-115.])
Me2SnCl2(DMSO)2 95.2 (3) 83.7 (5) 172.7 (3) Aslanov et al. (1978[Aslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S. (1978). Zh. Strukt. Khim. 19, 109-115.])
Ph2SnCl2(DMSO)2 97.43 (3) 79.34 (9) 172.17 (14) Sadiq-ur-Rehman et al. (2007[Sadiq-ur-Rehman, Saeed, S., Ali, S., Shahzadi, S. & Helliwell, M. (2007). Acta Cryst. E63, m1788.])
(4-FC6H4CH2)2SnCl2(DMSO)2 180 180 180 This work

6. Synthesis and crystallization

All chemicals and solvents were used as purchased without purification. Di(p-fluoro­benz­yl)tin dichloride was prepared in accordance with the literature method (Sisido et al., 1961[Sisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538-541.]). All reactions were carried out under ambient conditions. The melting point was determined using an Electrothermal digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Perkin Elmer Spectrum 400 FT Mid-IR/Far-IR spectrophotometer in the range 4000 to 400 cm−1. The 1H NMR spectrum was recorded at room temperature in CDCl3 solution on a Jeol ECA 400 MHz FT–NMR spectrometer.

N,N′-1,1,2,2-Di­nitrile­vinyl­enebis(5-bromo­salicylaldiminato) (1.0 mmol, 0.401 g; prepared by the condensation reaction between di­amino­maleo­nitrile and 5-bromo­sal­icyl­alde­hyde in a 2:1 molar ratio in ethanol) and tri­ethyl­amine (1.0 mmol, 0.14 ml) in ethyl acetate (25 ml) was added to di(p-fluoro­benz­yl)tin dichloride (1.0 mmol, 0.183 g) in ethyl acetate (10 ml). The resulting mixture was stirred and refluxed for 4 h. The filtrate was evaporated until a dark-orange precipitate was obtained. The precipitate was dissolved in DMSO-d6 solution in a NMR tube for 1H NMR spectroscopic characterization. After the analysis, the tube was set aside for a month and colourless crystals of (I)[link] suitable for X-ray crystallographic studies were obtained from the slow evaporation. Yield: 0.060 g, 11%; m.p: 399 K. IR (cm−1): 1595(m) ν(C=C), 1504(s) ν(S=O), 1161(m), 578(w), 508(m) ν(Sn—O). 1H NMR (in CDCl3): 6.90–7.11, 7.35–7.40 (m, 8H, aromatic-H), 3.11 (s, 6H, –CH3), 2.17 (m, 4H, –CH2).

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 6[link]. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

Table 6
Experimental details

Crystal data
Chemical formula [Sn(C7H6F)2Cl2(C2H6OS)2]
Mr 564.08
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 8.2363 (1), 12.7020 (2), 11.4038 (1)
β (°) 110.391 (2)
V3) 1118.28 (3)
Z 2
Radiation type Cu Kα
μ (mm−1) 13.28
Crystal size (mm) 0.24 × 0.12 × 0.10
 
Data collection
Diffractometer Agilent SuperNova, Dual, Cu at zero, AtlasS2
Absorption correction Multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.])
Tmin, Tmax 0.636, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 7792, 2292, 2228
Rint 0.020
(sin θ/λ)max−1) 0.631
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.018, 0.046, 1.08
No. of reflections 2292
No. of parameters 126
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.35, −0.76
Computer programs: CrysAlis PRO (Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Dichloridobis(dimethyl sulfoxide-κO)bis(4-fluorobenzyl-κC1)tin(IV) top
Crystal data top
[Sn(C7H6F)2Cl2(C2H6OS)2]F(000) = 564
Mr = 564.08Dx = 1.675 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.2363 (1) ÅCell parameters from 6127 reflections
b = 12.7020 (2) Åθ = 5.4–76.3°
c = 11.4038 (1) ŵ = 13.28 mm1
β = 110.391 (2)°T = 100 K
V = 1118.28 (3) Å3Prism, colourless
Z = 20.24 × 0.12 × 0.10 mm
Data collection top
Agilent SuperNova, Dual, Cu at zero, AtlasS2
diffractometer
2292 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source2228 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.020
ω scansθmax = 76.5°, θmin = 5.4°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
h = 109
Tmin = 0.636, Tmax = 1.000k = 1515
7792 measured reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.046 w = 1/[σ2(Fo2) + (0.0233P)2 + 0.7527P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2292 reflectionsΔρmax = 0.35 e Å3
126 parametersΔρmin = 0.76 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn0.50000.50000.50000.00673 (6)
Cl10.44665 (6)0.48762 (3)0.26545 (4)0.01508 (10)
S10.55778 (5)0.24628 (3)0.43015 (3)0.00881 (9)
F10.06456 (15)0.03219 (9)0.34347 (11)0.0248 (2)
O10.60349 (15)0.33583 (9)0.52752 (10)0.0106 (2)
C10.2332 (2)0.45714 (13)0.46551 (16)0.0130 (3)
H1A0.20540.47460.54100.016*
H1B0.15830.50130.39620.016*
C20.1878 (2)0.34437 (13)0.43339 (15)0.0098 (3)
C30.1093 (2)0.31260 (13)0.30871 (15)0.0111 (3)
H30.08380.36370.24400.013*
C40.0679 (2)0.20772 (14)0.27783 (15)0.0134 (3)
H40.01470.18680.19300.016*
C50.1058 (2)0.13487 (13)0.37280 (16)0.0140 (3)
C60.1822 (2)0.16192 (14)0.49747 (16)0.0144 (3)
H60.20620.11010.56130.017*
C70.2229 (2)0.26727 (14)0.52668 (15)0.0121 (3)
H70.27580.28730.61180.014*
C80.6371 (2)0.13286 (13)0.52466 (15)0.0154 (3)
H8A0.75760.14470.57860.023*
H8B0.63120.07180.47080.023*
H8C0.56620.11970.57660.023*
C90.7181 (2)0.25482 (14)0.35875 (16)0.0159 (3)
H9A0.70350.32090.31180.024*
H9B0.70550.19520.30170.024*
H9C0.83350.25300.42350.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.00785 (9)0.00543 (9)0.00565 (8)0.00005 (4)0.00078 (6)0.00080 (4)
Cl10.0208 (2)0.0153 (2)0.00719 (18)0.00143 (14)0.00249 (16)0.00013 (13)
S10.00860 (18)0.00802 (18)0.00877 (16)0.00079 (13)0.00171 (14)0.00157 (13)
F10.0250 (6)0.0089 (5)0.0328 (6)0.0026 (4)0.0006 (5)0.0014 (5)
O10.0135 (6)0.0067 (5)0.0095 (5)0.0016 (4)0.0012 (4)0.0021 (4)
C10.0082 (7)0.0131 (9)0.0172 (8)0.0007 (6)0.0039 (6)0.0030 (6)
C20.0059 (7)0.0112 (8)0.0122 (7)0.0000 (6)0.0032 (6)0.0012 (6)
C30.0087 (7)0.0129 (8)0.0105 (7)0.0005 (6)0.0018 (6)0.0023 (6)
C40.0115 (8)0.0152 (9)0.0117 (7)0.0004 (6)0.0020 (6)0.0028 (6)
C50.0110 (8)0.0078 (8)0.0211 (8)0.0014 (6)0.0030 (6)0.0018 (6)
C60.0117 (8)0.0151 (8)0.0152 (8)0.0015 (6)0.0032 (6)0.0065 (6)
C70.0089 (8)0.0176 (8)0.0090 (7)0.0006 (6)0.0022 (6)0.0000 (6)
C80.0228 (9)0.0080 (8)0.0141 (8)0.0027 (6)0.0049 (7)0.0002 (6)
C90.0166 (9)0.0175 (9)0.0167 (8)0.0005 (6)0.0097 (7)0.0019 (6)
Geometric parameters (Å, º) top
Sn—C12.1628 (16)C3—C41.390 (2)
Sn—C1i2.1628 (16)C3—H30.9500
Sn—O12.2332 (11)C4—C51.375 (2)
Sn—O1i2.2332 (11)C4—H40.9500
Sn—Cl1i2.5599 (4)C5—C61.383 (2)
Sn—Cl12.5599 (4)C6—C71.392 (2)
S1—O11.5417 (11)C6—H60.9500
S1—C91.7796 (17)C7—H70.9500
S1—C81.7815 (17)C8—H8A0.9800
F1—C51.360 (2)C8—H8B0.9800
C1—C21.494 (2)C8—H8C0.9800
C1—H1A0.9900C9—H9A0.9800
C1—H1B0.9900C9—H9B0.9800
C2—C71.400 (2)C9—H9C0.9800
C2—C31.401 (2)
C1—Sn—C1i180.0C4—C3—C2121.27 (15)
C1—Sn—O195.99 (5)C4—C3—H3119.4
C1—Sn—Cl190.05 (5)C2—C3—H3119.4
C1—Sn—Cl1i89.95 (5)C5—C4—C3118.50 (15)
C1—Sn—O1i84.01 (5)C5—C4—H4120.8
C1—Sn—Cl1i89.95 (5)C3—C4—H4120.8
O1—Sn—Cl190.44 (3)F1—C5—C4118.88 (15)
O1—Sn—Cl1i89.56 (3)F1—C5—C6118.46 (15)
C1i—Sn—O184.01 (5)C4—C5—C6122.66 (16)
C1i—Sn—O1i95.99 (5)C5—C6—C7118.07 (15)
O1—Sn—O1i180.0C5—C6—H6121.0
C1i—Sn—Cl1i90.05 (5)C7—C6—H6121.0
O1i—Sn—Cl1i90.44 (3)C6—C7—C2121.47 (15)
O1i—Sn—Cl189.56 (3)C6—C7—H7119.3
Cl1i—Sn—Cl1180.000 (18)C2—C7—H7119.3
O1—S1—C9104.51 (8)S1—C8—H8A109.5
O1—S1—C8102.41 (7)S1—C8—H8B109.5
C9—S1—C898.73 (8)H8A—C8—H8B109.5
S1—O1—Sn127.03 (6)S1—C8—H8C109.5
C2—C1—Sn115.97 (11)H8A—C8—H8C109.5
C2—C1—H1A108.3H8B—C8—H8C109.5
Sn—C1—H1A108.3S1—C9—H9A109.5
C2—C1—H1B108.3S1—C9—H9B109.5
Sn—C1—H1B108.3H9A—C9—H9B109.5
H1A—C1—H1B107.4S1—C9—H9C109.5
C7—C2—C3118.03 (15)H9A—C9—H9C109.5
C7—C2—C1121.12 (14)H9B—C9—H9C109.5
C3—C2—C1120.85 (15)
C9—S1—O1—Sn92.64 (10)C3—C4—C5—F1179.52 (15)
C8—S1—O1—Sn164.80 (9)C3—C4—C5—C60.4 (3)
Sn—C1—C2—C781.29 (17)F1—C5—C6—C7179.60 (15)
Sn—C1—C2—C398.42 (16)C4—C5—C6—C70.5 (3)
C7—C2—C3—C40.3 (2)C5—C6—C7—C20.1 (3)
C1—C2—C3—C4179.42 (15)C3—C2—C7—C60.2 (2)
C2—C3—C4—C50.0 (2)C1—C2—C7—C6179.50 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···F1ii0.952.493.333 (2)147
C6—H6···Cl1iii0.952.773.6129 (18)148
C8—H8B···Cl1iv0.982.763.6379 (17)150
C9—H9C···Cg1v0.982.673.3887 (19)130
Symmetry codes: (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x+1, y, z.
Summary of short interatomic contacts (Å) in (I) top
Contactdistancesymmetry operation
C4···C93.371 (2)-1 + x, y, z
F1···H8A2.661 - x, -y, 1 - z
Cl1···H9B2.911 - x, 1/2 + y, 1/2 - z
Note: (a) the SnIV atom is located on a centre of inversion.
Percentage contribution of interatomic contacts to the Hirshfeld surface for (I) top
Contactpercentage contribution
H···H45.7
Cl···H/H···Cl15.1
F···H/H···F19.8
C···H/H···C12.8
O···H/H···O4.1
S···H/H···S1.7
Cl···F/F···Cl0.6
C···Cl/Cl···C0.1
F···F0.1
Selected geometric parameters (Å, °) for molecules of the general formula R2SnX2(DMSO)2 top
CompoundX—Sn—XO—Sn—OC—Sn—CReference
Me2SnBr2(DMSO)2180180180Aslanov et al. (1978)
Me2SnCl2(DMSO)295.2 (3)83.7 (5)172.7 (3)Aslanov et al. (1978)
Ph2SnCl2(DMSO)297.43 (3)79.34 (9)172.17 (14)Sadiq-ur-Rehman et al. (2007)
(4-FC6H4CH2)2SnCl2(DMSO)2180180180This work
 

Footnotes

Additional correspondence author, e-mail: mmjotani@rediffmail.com.

Funding information

Funding for this research was provided by: Sunway University (award No. INT-RRO-2017–096); University of Malaya (award Nos. RP017A-2014AFR, PG239–2016\#65532;A); Ministry of Higher Education, Malaysia (MOHE) Fundamental Research Grant Scheme (award No. FP033–2014B).

References

First citationAslanov, L. A., Ionov, V. M., Attiya, V. M., Permin, A. B. & Petrosyan, V. S. (1978). Zh. Strukt. Khim. 19, 109–115.  CAS Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationContreras, R., Flores-Parra, A., Mijangos, E., Téllez, F., López-Sandoval, H. & Barba-Behrens, N. (2009). Coord. Chem. Rev. 253, 1979–1999.  Web of Science CrossRef CAS Google Scholar
First citationDey, D. K., Dasa, M. K. & Nöth, H. (1999). Z. Naturforsch. Teil B, 54, 145–154.  CAS Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationIsaacs, N. W. & Kennard, C. H. L. (1970). J. Chem. Soc. A, pp. 1257–1261.  CSD CrossRef Web of Science Google Scholar
First citationLee, S. M., Lo, K. M. & Ng, S. W. (2004). Acta Cryst. E60, m1614–m1616.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMcKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816.  Web of Science CrossRef Google Scholar
First citationRigaku Oxford Diffraction (2015). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.  Google Scholar
First citationSadiq-ur-Rehman, Saeed, S., Ali, S., Shahzadi, S. & Helliwell, M. (2007). Acta Cryst. E63, m1788.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSisido, K., Takeda, Y. & Kinugawa, Z. (1961). J. Am. Chem. Soc. 83, 538–541.  CrossRef Web of Science Google Scholar
First citationTeoh, S.-G., Yeap, G.-Y., Loh, C.-C., Foong, L.-W., Teo, S.-B. & Fun, H.-K. (1997). Polyhedron, 16, 2213–2221.  CSD CrossRef CAS Web of Science Google Scholar
First citationVallet, V., Wahlgren, U. & Grenthe, I. (2003). J. Am. Chem. Soc. 125, 14941–14950.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWardell, J. L., Jotani, M. M. & Tiekink, E. R. T. (2016). Acta Cryst. E72, 1618–1627.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYearwood, B., Parkin, S. & Atwood, D. A. (2002). Inorg. Chim. Acta, 333, 124–131.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds