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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN n-butyldichlorido{4-cyclohexyl-1-[1- (pyridin-2-yl-jn)ethylidene]thiosemicarbazidato-j 2 N 1,S}tin(IV) Md. Abu Affan, a Md. Abdus Salam, a Mohd Razip Asaruddin, a Seik Weng Ng b,c and Edward R. T. Tiekink b * a Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, Kota Samaharan, Sawarak, Malaysia, b Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia, and c Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box Jeddah, Saudi Arabia Correspondence Edward.Tiekink@gmail.com Received 5 June 2012; accepted 7 June 2012 Experimental Crystal data [Sn(C 4 H 9 )(C 14 H 19 N 4 S)Cl 2 ] M r = Monoclinic, P2 1 =n a = (3) Å b = (4) Å c = (6) Å = (3) Data collection Agilent SuperNova Dual diffractometer with Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T min = 0.794, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (19) Å 3 Z =8 Mo K radiation = 1.54 mm 1 T = 100 K mm measured reflections 9861 independent reflections 8503 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 1.64 e Å 3 min = 1.11 e Å 3 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.035; wr factor = 0.085; data-to-parameter ratio = Two independent molecules comprise the asymmetric unit in the title compound, [Sn(C 4 H 9 )(C 14 H 19 N 4 S)Cl 2 ]. In each molecule, the Sn IV atom exists within a distorted octahedral geometry defined by the N,N 0,S-tridentate mono-deprotonated Schiff base ligand, two mutually trans Cl atoms, and the -C atom of the n-butyl group; the latter is trans to the azo-n atom. The greatest distortion from the ideal geometry is found in the nominally trans angle formed by the S and pyridyl-n atoms at Sn [ (7) and (7), respectively]. In the crystal, molecules are consolidated into a three-dimensional architecture by a combination of N HCl, C H and interactions [inter-centroid distances = (19) and (2) Å]. Related literature For the structures of the methyltin and phenyltin derivatives, see: Salam et al. (2010a,b). Table 1 Selected bond lengths (Å). Sn1 C (3) Sn1 N (2) Sn1 N (2) Sn1 S (8) Sn1 Cl (8) Sn1 Cl (8) Table 2 Hydrogen-bond geometry (Å, ). Cg1 is the centroid of the N1,C5 C9 ring. Sn2 C (3) Sn2 N (3) Sn2 N (3) Sn2 S (8) Sn2 Cl (8) Sn2 Cl (8) D HA D H HA DA D HA N4 H4Cl (3) 167 C15 H15ACg1 i (4) 143 Symmetry code: (i) x þ 1; y þ 1; z þ 1. Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publcif (Westrip, 2010). This work was supported financially by the Ministry of Science Technology and Innovation (MOSTI) under research grant No SF0046. The authors would like to thank Universiti Malaysia Sarawak (UNIMAS) for the facilities to carry out the research work. They also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/ MOHE/SC/12). doi: /s Affan et al. m909

2 metal-organic compounds Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2072). References Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, Salam, M. A., Affan, M. A., Ahmad, F. B., Tahir, M. I. M. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, m1503 m1504. Salam, M. A., Affan, M. A., Shamsuddin, M. & Ng, S. W. (2010b). Acta Cryst. E66, m570. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2010). J. Appl. Cryst. 43, m910 Affan et al. [Sn(C 4 H 9 )(C 14 H 19 N 4 S)Cl 2 ]

3 supporting information [ n-butyldichlorido{4-cyclohexyl-1-[1-(pyridin-2-yl-κn)ethylidene]thiosemicarbazidato-κ 2 N 1,S}tin(IV) Md. Abu Affan, Md. Abdus Salam, Mohd Razip Asaruddin, Seik Weng Ng and Edward R. T. Tiekink S1. Comment Previous structural studies have described the methyltin (Salam et al., 2010a) and phenyltin (Salam et al., 2010b) derivatives of the title compound. The molecular structure of the title compound, (I), resembles these. There are two independent molecules in the asymmetric unit of (I), Fig. 1. These differ in terms of the relative dispositions of the n-butyl and cycohexyl rings, Fig. 2. The Sn atom in each molecule exists within a six atom CCl 2 N 2 S donor set defined by the tridentate mono-deprotonated Schiff base ligand, two mutually trans chlorido atoms, and the α-c atom of the Sn-bound n-butyl group which is trans to the azo-n atom, Table 1. Distortions from the ideal octahedral geometry are ascribed primarily to the restricted bite distances formed by the Schiff base which results in an angle of (7) [ (7) for the second molecule] for the nominally trans S Sn N angle. The molecules are consolidated into a three-dimensional architecture by a combination of N H Cl and C H π, Table 1, as well as π π interactions, the latter occurring between centrosymmetrically related pairs of (N1,C5 C9) and (N5,C23 C27) rings [inter-centroid distances = (19) and (2) Å for symmetry operations: 2 - x, 1 - y, 1 - z and -x, 1 - y, -z, respectively], Fig. 3 and Table 2. S2. Experimental 2-Acetylpyridine-N(4)-cyclohexylthiosemicarbazone (0.28 g, 1.0 mmol) was dissolved in absolute methanol (10 ml) in a Schlenk round bottom flask under a nitrogen atmosphere. Then, a 10 ml me thanolic solution of butyltin(iv) trichloride (0.282 g, 1.0 mmol) was added drop-wise while stirring which resulted in the formation of a yellow solution. The reaction mixture was refluxed for 4 h and then cooled to room temperature. The yellow microcrystals that formed were filtered off, washed with a small amount of cold methanol and dried in vacuo over silica gel. Yellow crystals suitable for X-ray diffraction were obtained from the slow evaporation of a chloroform/methanol (1:1 ratio) solution at room temperature. Yield: g, 78%: M.pt: K: FT IR (KBr, cm -1 ) ν max : 3308 (s, NH), 2931, 2855 (s, cyclohexyl), 1602 (m, C N N C), 1020 (w, N N), 1345, 833 (m, C S), 652 (w, pyridine in plane), 570 (w, Sn C), 475 (w, Sn N). Anal. Calc. for C 18 H 28 Cl 2 N 4 SSn: C, 41.40; H, 5.40; N, 10.73%. Found: C, 41.24; H, 5.17; N, 10.59%. S3. Refinement Carbon-bound H-atoms were placed in calculated positions [C H 0.95 to 0.98 Å, U iso (H) 1.2 to 1.5U eq (C)] and were included in the refinement in the riding model approximation. The amino H-atoms were similarly treated [N H 0.88 Å; U iso (H) 1.2U eq (N)]. The (0 1 2) reflection was omitted from the final refinement as it was affected by the beam-stop. The maximum and minimum residual electron density peaks of 1.64 and 1.11 e Å -3, respectively, were located 0.73 Å and 0.74 Å from the Sn1 and Sn2 atoms, respectively. sup-1

4 Figure 1 The molecular structures of the two independent molecules of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. sup-2

5 Figure 2 Superimposition of the two independent molecules in (I). The S,N-chelate rings have been superimposed, and the Sn1 and and Sn2-containing molecules are shown as red and blue images, respectively. sup-3

6 Figure 3 A view in projection down the a axis of the unit-cell contents for (I). The N H Cl, C H π and π π interactions are shown as orange, purple and brown dashed lines, respectively. n-butyldichlorido{4-cyclohexyl-1-[1-(pyridin-2-yl- κn)ethylidene]thiosemicarbazidato-κ 2 N 1,S}tin(IV) Crystal data [Sn(C 4 H 9 )(C 14 H 19 N 4 S)Cl 2 ] M r = Monoclinic, P2 1 /n Hall symbol: -P 2yn a = (3) Å b = (4) Å c = (6) Å β = (3) V = (19) Å 3 Z = 8 Data collection Agilent SuperNova Dual diffractometer with Atlas detector Radiation source: SuperNova (Mo) X-ray Source Mirror monochromator Detector resolution: pixels mm -1 F(000) = 2112 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from reflections θ = µ = 1.54 mm 1 T = 100 K Block, dark-yellow mm ω scan Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T min = 0.794, T max = measured reflections 9861 independent reflections sup-4

7 8503 reflections with I > 2σ(I) R int = θ max = 27.6, θ min = 2.2 Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 471 parameters 0 restraints Primary atom site location: structure-invariant direct methods h = k = l = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0351P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 1.64 e Å 3 Δρ min = 1.11 e Å 3 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Sn (17) (13) (9) (6) Sn (17) (13) (9) (6) Cl (6) (5) (3) (16) Cl (7) (6) (4) (19) Cl (6) (5) (3) (16) Cl (7) (5) (4) (19) S (7) (5) (3) (17) S (7) (5) (4) (17) N (2) (16) (11) (5) N (2) (16) (11) (5) N (2) (16) (11) (5) N (2) (17) (12) (6) H * N (2) (17) (11) (6) N (2) (16) (11) (5) N (2) (17) (11) (6) N (2) (17) (12) (6) H * C (3) (19) (13) (7) H1A * H1B * C (4) (3) (19) (10) H2A * H2B * C (4) (3) (2) (10) H3A * H3B * C (4) (3) (2) (13) H4A * H4B * H4C * sup-5

8 C (3) (2) (15) (7) H * C (3) (2) (15) (8) H * C (3) (3) (15) (8) H * C (3) (2) (14) (7) H8A * C (2) (2) (13) (6) C (3) (2) (14) (6) C (3) (2) (17) (9) H11A * H11B * H11C * C (3) (2) (14) (6) C (3) (19) (13) (6) H * C (3) (2) (15) (7) H14A * H14B * C (3) (2) (16) (8) H15A * H15B * C (3) (2) (18) (9) H16A * H16B * C (4) (2) (17) (10) H17A * H17B * C (3) (2) (15) (8) H18A * H18B * C (3) (18) (13) (6) H19A * H19B * C (3) (2) (16) (8) H20A * H20B * C (3) (2) (16) (8) H21A * H21B * C (3) (2) (17) (8) H22A * H22B * H22C * C (3) (2) (15) (7) H * C (3) (2) (16) (8) sup-6

9 H * C (3) (2) (15) (7) H * C (3) (2) (14) (7) H * C (3) (2) (14) (7) C (3) (2) (14) (6) C (3) (2) (15) (8) H29A * H29B * H29C * C (3) (19) (14) (6) C (3) (2) (14) (6) H * C (3) (2) (16) (7) H32A * H32B * C (3) (2) (16) (8) H33A * H33B * C (3) (2) (15) (7) H34A * H34B * C (3) (2) (15) (7) H35A * H35B * C (3) (2) (14) (7) H36A * H36B * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Sn (11) (11) (11) (8) (8) (7) Sn (11) (11) (12) (8) (9) (8) Cl (4) (4) (4) (3) (3) (3) Cl (4) (5) (4) (4) (4) (4) Cl (4) (4) (4) (3) (3) (3) Cl (4) (4) (5) (3) (4) (3) S (4) (4) (4) (3) (3) (3) S (4) (4) (4) (3) (3) (3) N (12) (13) (13) (11) (10) (10) N (12) (12) (13) (10) (10) (10) N (12) (13) (14) (11) (11) (11) N (13) (13) (13) (11) (11) (11) N (13) (13) (14) (11) (11) (11) N (12) (13) (14) (11) (10) (11) N (12) (13) (14) (11) (11) (11) sup-7

10 N (13) (13) (14) (11) (11) (11) C (16) (15) (14) (13) (12) (12) C (2) (2) (2) (19) (2) (18) C (3) (2) (3) (2) (2) (2) C (3) (3) (3) (3) (2) (2) C (15) (17) (17) (14) (13) (14) C (16) (2) (17) (15) (14) (15) C (16) (2) (16) (16) (13) (16) C (16) (19) (17) (15) (14) (14) C (14) (16) (15) (13) (12) (13) C (15) (16) (16) (13) (13) (13) C (19) (19) (2) (16) (16) (16) C (15) (15) (16) (13) (13) (12) C (15) (14) (16) (12) (13) (12) C (17) (16) (17) (14) (14) (13) C (19) (18) (2) (16) (16) (15) C (19) (2) (2) (16) (18) (17) C (3) (19) (2) (19) (19) (16) C (2) (18) (18) (16) (15) (14) C (15) (13) (14) (12) (12) (11) C (19) (17) (2) (15) (16) (15) C (19) (18) (2) (15) (16) (15) C (19) (19) (2) (16) (17) (17) C (16) (17) (18) (14) (14) (14) C (16) (19) (19) (15) (14) (15) C (16) (2) (17) (15) (13) (15) C (16) (18) (17) (14) (13) (14) C (15) (16) (16) (13) (12) (13) C (15) (16) (16) (13) (12) (13) C (17) (18) (18) (15) (14) (14) C (15) (15) (16) (12) (13) (12) C (15) (15) (16) (13) (13) (13) C (16) (16) (2) (14) (15) (15) C (18) (16) (2) (15) (16) (14) C (18) (16) (18) (15) (15) (14) C (16) (18) (18) (14) (14) (14) C (15) (15) (16) (13) (13) (13) Geometric parameters (Å, º) Sn1 C (3) C13 H Sn1 N (2) C14 C (4) Sn1 N (2) C14 H14A Sn1 S (8) C14 H14B Sn1 Cl (8) C15 C (5) Sn1 Cl (8) C15 H15A Sn2 C (3) C15 H15B Sn2 N (3) C16 C (5) sup-8

11 Sn2 N (3) C16 H16A Sn2 S (8) C16 H16B Sn2 Cl (8) C17 C (5) Sn2 Cl (8) C17 H17A S1 C (3) C17 H17B S2 C (3) C18 H18A N1 C (4) C18 H18B N1 C (4) C19 C (5) N2 C (4) C19 H19A N2 N (3) C19 H19B N3 C (4) C20 C (5) N4 C (4) C20 H20A N4 C (4) C20 H20B N4 H C21 C (5) N5 C (4) C21 H21A N5 C (4) C21 H21B N6 C (4) C22 H22A N6 N (3) C22 H22B N7 C (4) C22 H22C N8 C (4) C23 C (5) N8 C (4) C23 H N8 H C24 C (5) C1 C (5) C24 H C1 H1A C25 C (5) C1 H1B C25 H C2 C (6) C26 C (5) C2 H2A C26 H C2 H2B C27 C (4) C3 C (6) C28 C (4) C3 H3A C29 H29A C3 H3B C29 H29B C4 H4A C29 H29C C4 H4B C31 C (4) C4 H4C C31 C (4) C5 C (5) C31 H C5 H C32 C (5) C6 C (5) C32 H32A C6 H C32 H32B C7 C (5) C33 C (5) C7 H C33 H33A C8 C (4) C33 H33B C8 H8A C34 C (5) C9 C (4) C34 H34A C10 C (4) C34 H34B C11 H11A C35 C (4) C11 H11B C35 H35A C11 H11C C35 H35B C13 C (4) C36 H36A sup-9

12 C13 C (4) C36 H36B C1 Sn1 N (11) C15 C14 H14B C1 Sn1 N (10) H14A C14 H14B N2 Sn1 N (9) C16 C15 C (3) C1 Sn1 S (8) C16 C15 H15A N2 Sn1 S (7) C14 C15 H15A N1 Sn1 S (7) C16 C15 H15B C1 Sn1 Cl (9) C14 C15 H15B N2 Sn1 Cl (7) H15A C15 H15B N1 Sn1 Cl (7) C15 C16 C (3) S1 Sn1 Cl (3) C15 C16 H16A C1 Sn1 Cl (9) C17 C16 H16A N2 Sn1 Cl (7) C15 C16 H16B N1 Sn1 Cl (6) C17 C16 H16B S1 Sn1 Cl (3) H16A C16 H16B Cl2 Sn1 Cl (3) C16 C17 C (3) C19 Sn2 N (10) C16 C17 H17A C19 Sn2 N (10) C18 C17 H17A N6 Sn2 N (9) C16 C17 H17B C19 Sn2 S (8) C18 C17 H17B N6 Sn2 S (7) H17A C17 H17B N5 Sn2 S (7) C13 C18 C (3) C19 Sn2 Cl (8) C13 C18 H18A N6 Sn2 Cl (7) C17 C18 H18A N5 Sn2 Cl (7) C13 C18 H18B S2 Sn2 Cl (3) C17 C18 H18B C19 Sn2 Cl (8) H18A C18 H18B N6 Sn2 Cl (7) C20 C19 Sn (19) N5 Sn2 Cl (7) C20 C19 H19A S2 Sn2 Cl (3) Sn2 C19 H19A Cl3 Sn2 Cl (3) C20 C19 H19B C12 S1 Sn (11) Sn2 C19 H19B C30 S2 Sn (11) H19A C19 H19B C5 N1 C (3) C21 C20 C (3) C5 N1 Sn (2) C21 C20 H20A C9 N1 Sn (19) C19 C20 H20A C10 N2 N (3) C21 C20 H20B C10 N2 Sn (2) C19 C20 H20B N3 N2 Sn (18) H20A C20 H20B C12 N3 N (2) C22 C21 C (3) C12 N4 C (3) C22 C21 H21A C12 N4 H C20 C21 H21A C13 N4 H C22 C21 H21B C23 N5 C (3) C20 C21 H21B C23 N5 Sn (2) H21A C21 H21B C27 N5 Sn (19) C21 C22 H22A C28 N6 N (3) C21 C22 H22B sup-10

13 C28 N6 Sn (2) H22A C22 H22B N7 N6 Sn (19) C21 C22 H22C C30 N7 N (3) H22A C22 H22C C30 N8 C (3) H22B C22 H22C C30 N8 H N5 C23 C (3) C31 N8 H N5 C23 H C2 C1 Sn (2) C24 C23 H C2 C1 H1A C25 C24 C (3) Sn1 C1 H1A C25 C24 H C2 C1 H1B C23 C24 H Sn1 C1 H1B C24 C25 C (3) H1A C1 H1B C24 C25 H C1 C2 C (3) C26 C25 H C1 C2 H2A C27 C26 C (3) C3 C2 H2A C27 C26 H C1 C2 H2B C25 C26 H C3 C2 H2B N5 C27 C (3) H2A C2 H2B N5 C27 C (3) C4 C3 C (4) C26 C27 C (3) C4 C3 H3A N6 C28 C (3) C2 C3 H3A N6 C28 C (3) C4 C3 H3B C27 C28 C (3) C2 C3 H3B C28 C29 H29A H3A C3 H3B C28 C29 H29B C3 C4 H4A H29A C29 H29B C3 C4 H4B C28 C29 H29C H4A C4 H4B H29A C29 H29C C3 C4 H4C H29B C29 H29C H4A C4 H4C N7 C30 N (3) H4B C4 H4C N7 C30 S (2) N1 C5 C (3) N8 C30 S (2) N1 C5 H N8 C31 C (3) C6 C5 H N8 C31 C (2) C7 C6 C (3) C32 C31 C (3) C7 C6 H N8 C31 H C5 C6 H C32 C31 H C6 C7 C (3) C36 C31 H C6 C7 H C31 C32 C (3) C8 C7 H C31 C32 H32A C9 C8 C (3) C33 C32 H32A C9 C8 H8A C31 C32 H32B C7 C8 H8A C33 C32 H32B N1 C9 C (3) H32A C32 H32B N1 C9 C (3) C32 C33 C (3) C8 C9 C (3) C32 C33 H33A N2 C10 C (3) C34 C33 H33A N2 C10 C (3) C32 C33 H33B C9 C10 C (3) C34 C33 H33B sup-11

14 C10 C11 H11A H33A C33 H33B C10 C11 H11B C35 C34 C (3) H11A C11 H11B C35 C34 H34A C10 C11 H11C C33 C34 H34A H11A C11 H11C C35 C34 H34B H11B C11 H11C C33 C34 H34B N3 C12 N (3) H34A C34 H34B N3 C12 S (2) C34 C35 C (3) N4 C12 S (2) C34 C35 H35A N4 C13 C (3) C36 C35 H35A N4 C13 C (3) C34 C35 H35B C18 C13 C (3) C36 C35 H35B N4 C13 H H35A C35 H35B C18 C13 H C31 C36 C (3) C14 C13 H C31 C36 H36A C13 C14 C (3) C35 C36 H36A C13 C14 H14A C31 C36 H36B C15 C14 H14A C35 C36 H36B C13 C14 H14B H36A C36 H36B C1 Sn1 S1 C (14) C7 C8 C9 C (3) N2 Sn1 S1 C (12) N3 N2 C10 C (2) N1 Sn1 S1 C (18) Sn1 N2 C10 C9 0.4 (4) Cl2 Sn1 S1 C (11) N3 N2 C10 C (5) Cl1 Sn1 S1 C (11) Sn1 N2 C10 C (3) C19 Sn2 S2 C (13) N1 C9 C10 N2 1.9 (4) N6 Sn2 S2 C (12) C8 C9 C10 N (3) N5 Sn2 S2 C (18) N1 C9 C10 C (3) Cl3 Sn2 S2 C (11) C8 C9 C10 C (5) Cl4 Sn2 S2 C (11) N2 N3 C12 N (2) C1 Sn1 N1 C5 3.2 (3) N2 N3 C12 S1 1.6 (4) N2 Sn1 N1 C (3) C13 N4 C12 N3 0.2 (4) S1 Sn1 N1 C (18) C13 N4 C12 S (2) Cl2 Sn1 N1 C (2) Sn1 S1 C12 N3 0.5 (3) Cl1 Sn1 N1 C (2) Sn1 S1 C12 N (2) C1 Sn1 N1 C (2) C12 N4 C13 C (3) N2 Sn1 N1 C9 1.6 (2) C12 N4 C13 C (4) S1 Sn1 N1 C9 5.7 (3) N4 C13 C14 C (3) Cl2 Sn1 N1 C (2) C18 C13 C14 C (4) Cl1 Sn1 N1 C (2) C13 C14 C15 C (4) N1 Sn1 N2 C (2) C14 C15 C16 C (4) S1 Sn1 N2 C (2) C15 C16 C17 C (4) Cl2 Sn1 N2 C (2) N4 C13 C18 C (3) Cl1 Sn1 N2 C (2) C14 C13 C18 C (4) N1 Sn1 N2 N (2) C16 C17 C18 C (4) S1 Sn1 N2 N3 1.3 (2) N5 Sn2 C19 C (2) Cl2 Sn1 N2 N (2) S2 Sn2 C19 C (2) Cl1 Sn1 N2 N (2) Cl3 Sn2 C19 C (2) sup-12

15 C10 N2 N3 C (3) Cl4 Sn2 C19 C (2) Sn1 N2 N3 C (4) Sn2 C19 C20 C (2) C19 Sn2 N5 C (3) C19 C20 C21 C (3) N6 Sn2 N5 C (3) C27 N5 C23 C (5) S2 Sn2 N5 C (18) Sn2 N5 C23 C (2) Cl3 Sn2 N5 C (2) N5 C23 C24 C (5) Cl4 Sn2 N5 C (2) C23 C24 C25 C (5) C19 Sn2 N5 C (2) C24 C25 C26 C (5) N6 Sn2 N5 C (2) C23 N5 C27 C (5) S2 Sn2 N5 C (3) Sn2 N5 C27 C (2) Cl3 Sn2 N5 C (2) C23 N5 C27 C (3) Cl4 Sn2 N5 C (2) Sn2 N5 C27 C (3) N5 Sn2 N6 C (2) C25 C26 C27 N5 0.2 (5) S2 Sn2 N6 C (2) C25 C26 C27 C (3) Cl3 Sn2 N6 C (2) N7 N6 C28 C (3) Cl4 Sn2 N6 C (2) Sn2 N6 C28 C (4) N5 Sn2 N6 N (2) N7 N6 C28 C (5) S2 Sn2 N6 N7 0.9 (2) Sn2 N6 C28 C (2) Cl3 Sn2 N6 N (2) N5 C27 C28 N6 2.3 (4) Cl4 Sn2 N6 N (2) C26 C27 C28 N (3) C28 N6 N7 C (3) N5 C27 C28 C (3) Sn2 N6 N7 C (4) C26 C27 C28 C (5) N1 Sn1 C1 C (3) N6 N7 C30 N (3) S1 Sn1 C1 C (2) N6 N7 C30 S2 3.6 (4) Cl2 Sn1 C1 C (3) C31 N8 C30 N7 0.9 (4) Cl1 Sn1 C1 C (2) C31 N8 C30 S (2) Sn1 C1 C2 C (4) Sn2 S2 C30 N7 3.7 (3) C1 C2 C3 C (5) Sn2 S2 C30 N (2) C9 N1 C5 C6 0.6 (5) C30 N8 C31 C (4) Sn1 N1 C5 C (2) C30 N8 C31 C (3) N1 C5 C6 C7 0.5 (5) N8 C31 C32 C (3) C5 C6 C7 C8 0.1 (5) C36 C31 C32 C (4) C6 C7 C8 C9 0.2 (5) C31 C32 C33 C (4) C5 N1 C9 C8 0.3 (4) C32 C33 C34 C (4) Sn1 N1 C9 C (2) C33 C34 C35 C (4) C5 N1 C9 C (3) N8 C31 C36 C (3) Sn1 N1 C9 C (3) C32 C31 C36 C (4) C7 C8 C9 N1 0.1 (5) C34 C35 C36 C (4) Hydrogen-bond geometry (Å, º) Cg1 is the centroid of the N1,C5 C9 ring. D H A D H H A D A D H A N4 H4 Cl (3) 167 C15 H15A Cg1 i (4) 143 Symmetry code: (i) x+1, y+1, z+1. sup-13