metal-organic compounds

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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Pentakis(2-oxo-2,3-dihydropyrimidin-1- ium) di-l 3 -chlorido-tri-l 2 -chlorido-hexachloridotricadmate(ii) Mukhtar A. Kurawa, Christopher J. Adams and A. Guy Orpen* School of Chemistry, University of Bristol, Bristol BS8 1TS, England Correspondence guy.orpen@bris.ac.uk Received 10 June 2008; accepted 19 June 2008 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.026; wr factor = 0.058; data-to-parameter ratio = Experimental Crystal data (C 4 H 5 N 2 O) 5 [Cd 3 Cl 11 ] M r = Monoclinic, P2 1 =c a = (2) Å b = (2) Å c = (6) Å = (2) Data collection Oxford Diffraction Gemini-R Ultra diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) T min = 0.522, T max = 0.91 Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (10) Å 3 Z =4 Mo K radiation = 2.53 mm 1 T = 100 (2) K mm measured reflections independent reflections 7919 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.99 e Å 3 min = 1.09 e Å 3 The title compound, (C 4 H 5 N 2 O) 5 [Cd 3 Cl 11 ], was obtained from the reaction of 2-hydroxypyrimidine hydrochloride and cadmium(ii) chloride in concentrated HCl solution. The crystal structure consists of planar 2-oxo-1,2-dihydropyrimidin-3-ium cations with both N atoms protonated and the O atom unprotonated, and a complex trinuclear [Cd 3 Cl 11 ] 5 anion of approximately D 3h symmetry, which has a triangle of three octahedrally coordinated Cd II centres bonded to 11 chloride ions. Three of the chloride ions bridge adjacent Cd atoms, two cap the faces of the Cd 3 triangle and the remaining six are terminally bonded and act as hydrogenbond acceptors. Various N HCl hydrogen bonds connect the anions and cations and, in addition, intermolecular N HO hydrogen bonds contribute to the formation of a threedimensional network. Related literature A related salt of the same anion in the orthorhombic crystal system has been reported with [(CH 3 ) 2 NH 2 ] + cations (Waśkowska et al., 1990), while Furberg & Aas (1975) described the structure of the same cation as its chloride salt. Table 1 Selected bond lengths (Å). Cd1 Cl (6) Cd1 Cl (6) Cd1 Cl (6) Cd1 Cl (6) Cd1 Cl (6) Cd1 Cl (6) Cd2 Cl (6) Cd2 Cl (6) Cd2 Cl (6) Table 2 Hydrogen-bond geometry (Å, ). Cd2 Cl (6) Cd2 Cl (6) Cd2 Cl (6) Cd3 Cl (6) Cd3 Cl (6) Cd3 Cl (6) Cd3 Cl (6) Cd3 Cl (6) Cd3 Cl (6) D HA D H HA DA D HA N2 H2ACl11 i (2) 138 N3 H3ACl8 ii (2) 144 N4 H4ACl10 iii (2) 169 N5 H5ACl7 iv (2) 151 N6 H6ACl1 v (2) 162 N7 H7AO2 vi (3) 167 N10 H10BCl7 vi (2) 157 N8 H8AO5 vii (3) 120 N8 H8AO4 viii (4) 150 N9 H9BO (3) 152 Symmetry codes: (i) x; y þ 1 2 ; z þ 1 2 ; (ii) x; y þ 1; z; (iii) x; y þ 1; z; (iv) x þ 1; y þ 1; z þ 1; (v) x; y þ 1 2 ; z þ 1 2 ; (vi) x; y; z þ 1; (vii) x þ 1; y þ 1; z þ 2; (viii) x þ 1; y þ 2; z þ 2. Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. MAK thanks Bayero University, Kano, Nigeria for funding. Oxford Diffraction Ltd are thanked for the loan of an Oxford Gemini-R Ultra diffractometer to the University of Bristol. m960 Kurawa et al. doi: /s x Acta Cryst. (2008). E64, m960 m961

2 metal-organic compounds Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2641). References Furberg, S. & Aas, J. B. (1975). Acta Chem. Scand. A29, Oxford Diffraction (2007). CrysAlis CCD. and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Sheldrick, G. M. (2008). Acta Cryst. A64, Waśkowska, A., Lis, T., Krzewska, U. & Czapla, Z. (1990). Acta Cryst. C46, Acta Cryst. (2008). E64, m960 m961 Kurawa et al. (C 4 H 5 N 2 O) 5 [Cd 3 Cl 11 ] m961

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4 Acta Cryst. (2008). E64, m960-m961 [ doi: /s x ] di- 3 -chlorido-tri- 2 -chlorido- Pentakis(2-oxo-2,3-dihydropyrimidin-1-ium) hexachloridotricadmate(ii) M. A. Kurawa, C. J. Adams and A. G. Orpen Comment We sought to widen the use and exploitation of N H Cl interactions in the preparation of crystalline metal complexes by preparing [CdCl 4 ][C 4 H 5 N 2 O] 2 and the coordination network [CdCl 2 (C 4 H 4 N 2 O) 2 ]. However, the title compound I was obtained instead, crystallizing in a monoclinic cell with the P2 1 /c space group and an asymmetric unit consisting of five [C 4 H 5 N 2 O] + cations and one [Cd 3 Cl 11 ] 5- anion. The crystal structure of a related complex determined at room temperature with a [Cd 3 Cl 11 ] 5- anion and [(CH 3 ) 2 NH 2 ] + cations in the Cmcm space group revealed two alternating layers of cations and anions parallel to the (0 0 1) plane. This arrangement differs from that in the title compound I due to a complex three-dimensional hydrogen bond network involving anion-cation N H Cl and cation-cation N H O bonds. In contrast, the pyrimidin-2-onium cations reported in the related crystal structure (Furberg & Aas, 1975) display no N H O interactions. Experimental The title compound was obtained from an attempt to synthesize bis-2-hydroxypyrimidinium tetrachlorocadmate(ii). 2-hydroxypyrimidine hydrochloride and cadmium(ii) chloride in a 2:1 molar ratio were dissolved in concentrated hydrochloric acid solution. This was left to evaporate slowly at room temperature and resulted in the formation of needle-shaped colourless crystals. Refinement H atoms were positioned geometrically and refined using a riding model, with C H = 0.93 Å and N H = 0.86 Å and U iso (H) = 1.2 times U eq (C, N). Figures Fig. 1. The molecular structure of I with atom labels and 50% probability displacement ellipsoids for non-h atoms. sup-1

5 Fig. 2. Geometry of the [Cd 3 Cl 11 ] 5- anion. Fig. 3. Hydrogen bond (dotted lines) environment around the [Cd 3 Cl 11 ] 5- anion. Pentakis(2-oxo-2,3-dihydropyrimidin-1-ium) di-µ 3 -chlorido-tri-µ 2 -chlorido-hexachloridotricadmium(ii) Crystal data C 4 H 5 N 2 O) 5 [Cd 3 Cl 11 ] F 000 = 2344 M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc D x = Mg m 3 Mo Kα radiation λ = Å a = (2) Å θ = º b = (2) Å c = (6) Å β = (2)º V = (10) Å 3 Z = 4 Cell parameters from reflections µ = 2.53 mm 1 T = 100 (2) K Needle, colourless mm Data collection Oxford Diffraction Gemini-R Ultra diffractometer Radiation source: fine-focus sealed tube Monochromator: graphite R int = Detector resolution: pixels mm -1 θ max = 30.1º T = 100(2) K θ min = 2.4º 1 width ω scans h = Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) T min = 0.522, T max = measured reflections independent reflections 7919 reflections with I > 2σ(I) k = l = Refinement Refinement on F 2 Secondary atom site location: difference Fourier map sup-2

6 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained wr(f 2 ) = w = 1/[σ 2 (F 2 o ) + (0.0307P) 2 ] where P = (F 2 o + 2F 2 c )/3 S = 0.96 (Δ/σ) max = reflections Δρ max = 0.99 e Å parameters Δρ min = 1.09 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none Special details 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq Cd (10) (2) (6) (4) Cd (10) (2) (6) (4) Cd (10) (2) (6) (4) Cl (3) (8) (2) (13) Cl (4) (8) (2) (13) Cl (3) (8) (2) (12) Cl (3) (7) (2) (12) Cl (3) (8) (2) (12) Cl (3) (7) (2) (11) Cl (4) (8) (2) (12) Cl (3) (8) (2) (12) Cl (3) (8) (2) (12) Cl (3) (8) (2) (12) Cl (3) (8) (2) (12) N (12) (3) (8) (4) H1A * N (12) (3) (8) (5) H2A * N (13) (3) (8) (5) H3A * N (11) (3) (7) (4) H4A * sup-3

7 N (12) (3) (8) (5) H5A * N (12) (3) (7) (5) H6A * N (12) (3) (8) (5) H7A * N (14) (3) (10) (7) H8A * N (12) (3) (8) (5) H9B * N (13) (3) (8) (5) H10B * O (11) (2) (6) (4) O (11) (3) (7) (4) O (11) (3) (7) (5) O (14) (3) (8) (7) O (11) (3) (7) (5) C (14) (3) (9) (5) H1B * C (15) (3) (9) (5) H2B * C (15) (3) (9) (5) H3B * C (14) (3) (9) (5) C (17) (3) (10) (6) H5B * C (16) (3) (10) (6) H6B * C (15) (3) (9) (6) H7B * C (14) (3) (9) (5) C (14) (3) (9) (5) H9A * C (15) (3) (10) (6) H10A * C (15) (3) (10) (6) H11A * C (14) (3) (9) (5) C (16) (3) (10) (6) H13A * C (15) (3) (10) (6) H14A * C (16) (4) (11) (6) H15A * C (17) (4) (10) (7) C (16) (3) (10) (6) H17A * C (15) (3) (10) (6) H18A * sup-4

8 C (16) (4) (9) (6) H19A * C (16) (3) (9) (6) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Cd (9) (10) (8) (7) (6) (7) Cd (8) (10) (8) (7) (6) (7) Cd (8) (10) (8) (7) (6) (7) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (3) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) Cl (3) (3) (3) (2) (2) (2) N (11) (12) (10) (9) (8) (9) N (11) (12) (10) (10) (9) (9) N (11) (12) (11) (10) (9) (9) N (10) (11) (10) (9) (8) (8) N (10) (12) (11) (9) (8) (9) N (10) (12) (11) (9) (8) (9) N (11) (13) (11) (10) (9) (10) N (13) (18) (15) (12) (11) (13) N (11) (14) (10) (10) (9) (9) N (12) (14) (10) (10) (9) (9) O (10) (12) (9) (9) (8) (8) O (10) (12) (10) (9) (8) (9) O (9) (14) (10) (9) (8) (9) O (15) (17) (11) (13) (10) (11) O (10) (13) (10) (9) (8) (9) C (12) (14) (13) (10) (10) (11) C (13) (14) (12) (11) (10) (10) C (13) (14) (12) (11) (10) (10) C (12) (14) (13) (11) (10) (10) C (17) (15) (12) (13) (11) (11) C (15) (16) (12) (13) (11) (11) C (12) (15) (13) (11) (10) (11) C (12) (14) (12) (10) (9) (10) C (13) (14) (12) (11) (10) (10) C (12) (15) (13) (11) (10) (11) C (12) (14) (14) (10) (10) (11) C (12) (15) (12) (11) (10) (11) sup-5

9 C (13) (14) (13) (11) (11) (11) C (14) (14) (13) (12) (11) (11) C (13) (16) (17) (12) (12) (13) C (14) (19) (13) (14) (11) (13) C (14) (16) (12) (12) (10) (11) C (13) (15) (13) (11) (10) (11) C (14) (17) (13) (12) (11) (12) C (14) (15) (12) (12) (10) (10) Geometric parameters (Å, ) Cd1 Cl (6) N8 C (4) Cd1 Cl (6) N8 H8A Cd1 Cl (6) N9 C (3) Cd1 Cl (6) N9 C (3) Cd1 Cl (6) N9 H9B Cd1 Cl (6) N10 C (3) Cd2 Cl (6) N10 C (3) Cd2 Cl (6) N10 H10B Cd2 Cl (6) O1 C (3) Cd2 Cl (6) O2 C (3) Cd2 Cl (6) O3 C (3) Cd2 Cl (6) O4 C (3) Cd3 Cl (6) O5 C (3) Cd3 Cl (6) C1 C (3) Cd3 Cl (6) C1 H1B Cd3 Cl (6) C2 C (4) Cd3 Cl (6) C2 H2B Cd3 Cl (6) C3 H3B N1 C (3) C5 C (4) N1 C (3) C5 H5B N1 H1A C6 C (4) N2 C (3) C6 H6B N2 C (3) C7 H7B N2 H2A C9 C (4) N3 C (3) C9 H9A N3 C (3) C10 C (4) N3 H3A C10 H10A N4 C (3) C11 H11A N4 C (3) C12 O (3) N4 H4A C13 C (4) N5 C (3) C13 H13A N5 C (3) C14 C (4) N5 H5A C14 H14A N6 C (3) C15 H15A N6 C (3) C17 C (4) N6 H6A C17 H17A N7 C (3) C18 C (4) N7 C (4) C18 H18A sup-6

10 N7 H7A C19 H19A N8 C (4) Cl2 Cd1 Cl (2) C13 N7 H7A Cl2 Cd1 Cl (2) C16 N7 H7A Cl1 Cd1 Cl (2) C15 N8 C (2) Cl2 Cd1 Cl (2) C15 N8 H8A Cl1 Cd1 Cl (2) C16 N8 H8A Cl5 Cd1 Cl (18) C17 N9 C (2) Cl2 Cd1 Cl (2) C17 N9 H9B Cl1 Cd1 Cl (19) C20 N9 H9B Cl5 Cd1 Cl (18) C19 N10 C (2) Cl3 Cd1 Cl (18) C19 N10 H10B Cl2 Cd1 Cl (19) C20 N10 H10B Cl1 Cd1 Cl (19) N2 C1 C (2) Cl5 Cd1 Cl (18) N2 C1 H1B Cl3 Cd1 Cl (18) C2 C1 H1B Cl4 Cd1 Cl (18) C1 C2 C (2) Cl10 Cd2 Cl (2) C1 C2 H2B Cl10 Cd2 Cl (2) C3 C2 H2B Cl11 Cd2 Cl (19) N1 C3 C (2) Cl10 Cd2 Cl (19) N1 C3 H3B Cl11 Cd2 Cl (19) C2 C3 H3B Cl6 Cd2 Cl (18) O1 C4 N (2) Cl10 Cd2 Cl (19) O1 C4 N (2) Cl11 Cd2 Cl (19) N1 C4 N (2) Cl6 Cd2 Cl (18) N3 C5 C (2) Cl3 Cd2 Cl (19) N3 C5 H5B Cl10 Cd2 Cl (19) C6 C5 H5B Cl11 Cd2 Cl (19) C5 C6 C (2) Cl6 Cd2 Cl (18) C5 C6 H6B Cl3 Cd2 Cl (18) C7 C6 H6B Cl9 Cd2 Cl (18) N4 C7 C (2) Cl8 Cd3 Cl (2) N4 C7 H7B Cl8 Cd3 Cl (2) C6 C7 H7B Cl7 Cd3 Cl (19) O2 C8 N (2) Cl8 Cd3 Cl (19) O2 C8 N (2) Cl7 Cd3 Cl (19) N3 C8 N (2) Cl5 Cd3 Cl (19) N6 C9 C (2) Cl8 Cd3 Cl (2) N6 C9 H9A Cl7 Cd3 Cl (2) C10 C9 H9A Cl5 Cd3 Cl (18) C9 C10 C (2) Cl9 Cd3 Cl (18) C9 C10 H10A Cl8 Cd3 Cl (2) C11 C10 H10A Cl7 Cd3 Cl (19) N5 C11 C (2) Cl5 Cd3 Cl (18) N5 C11 H11A Cl9 Cd3 Cl (18) C10 C11 H11A Cl4 Cd3 Cl (18) O3 C12 N (2) Cd2 Cl3 Cd (18) O3 C12 N (2) Cd1 Cl4 Cd (17) O3 C12 N (2) sup-7

11 Cd1 Cl4 Cd (17) O3 C12 N (2) Cd3 Cl4 Cd (17) N5 C12 N (2) Cd3 Cl5 Cd (17) N7 C13 C (2) Cd2 Cl6 Cd (17) N7 C13 H13A Cd2 Cl6 Cd (17) C14 C13 H13A Cd3 Cl6 Cd (17) C15 C14 C (3) Cd3 Cl9 Cd (16) C15 C14 H14A C3 N1 C (2) C13 C14 H14A C3 N1 H1A N8 C15 C (3) C4 N1 H1A N8 C15 H15A C1 N2 C (2) C14 C15 H15A C1 N2 H2A O4 C16 N (3) C4 N2 H2A O4 C16 N (3) C5 N3 C (2) N8 C16 N (2) C5 N3 H3A N9 C17 C (2) C8 N3 H3A N9 C17 H17A C7 N4 C (2) C18 C17 H17A C7 N4 H4A C19 C18 C (2) C8 N4 H4A C19 C18 H18A C11 N5 C (2) C17 C18 H18A C11 N5 H5A N10 C19 C (2) C12 N5 H5A N10 C19 H19A C9 N6 C (2) C18 C19 H19A C9 N6 H6A O5 C20 N (2) C12 N6 H6A O5 C20 N (2) C13 N7 C (2) N10 C20 N (2) Cl10 Cd2 Cl3 Cd (19) Cl4 Cd3 Cl6 Cd (15) Cl11 Cd2 Cl3 Cd (19) Cl2 Cd1 Cl6 Cd (19) Cl6 Cd2 Cl3 Cd (17) Cl5 Cd1 Cl6 Cd (18) Cl9 Cd2 Cl3 Cd (5) Cl3 Cd1 Cl6 Cd (17) Cl4 Cd2 Cl3 Cd (17) Cl4 Cd1 Cl6 Cd (17) Cl2 Cd1 Cl3 Cd (19) Cl2 Cd1 Cl6 Cd (19) Cl1 Cd1 Cl3 Cd (19) Cl5 Cd1 Cl6 Cd (16) Cl5 Cd1 Cl3 Cd (5) Cl3 Cd1 Cl6 Cd (18) Cl4 Cd1 Cl3 Cd (17) Cl4 Cd1 Cl6 Cd (16) Cl6 Cd1 Cl3 Cd (16) Cl8 Cd3 Cl9 Cd (19) Cl2 Cd1 Cl4 Cd (10) Cl7 Cd3 Cl9 Cd (19) Cl1 Cd1 Cl4 Cd (18) Cl5 Cd3 Cl9 Cd (6) Cl5 Cd1 Cl4 Cd (16) Cl4 Cd3 Cl9 Cd (17) Cl3 Cd1 Cl4 Cd (18) Cl6 Cd3 Cl9 Cd (17) Cl6 Cd1 Cl4 Cd (16) Cl10 Cd2 Cl9 Cd (19) Cl2 Cd1 Cl4 Cd (10) Cl11 Cd2 Cl9 Cd (18) Cl1 Cd1 Cl4 Cd (18) Cl6 Cd2 Cl9 Cd (17) Cl5 Cd1 Cl4 Cd (18) Cl3 Cd2 Cl9 Cd (5) Cl3 Cd1 Cl4 Cd (17) Cl4 Cd2 Cl9 Cd (17) Cl6 Cd1 Cl4 Cd (16) C4 N2 C1 C2 0.5 (4) Cl8 Cd3 Cl4 Cd (10) N2 C1 C2 C3 1.0 (4) Cl7 Cd3 Cl4 Cd (17) C4 N1 C3 C2 1.4 (4) Cl5 Cd3 Cl4 Cd (17) C1 C2 C3 N1 1.5 (4) sup-8

12 Cl9 Cd3 Cl4 Cd (19) C3 N1 C4 O (2) Cl6 Cd3 Cl4 Cd (16) C3 N1 C4 N2 0.8 (3) Cl8 Cd3 Cl4 Cd (10) C1 N2 C4 O (2) Cl7 Cd3 Cl4 Cd (17) C1 N2 C4 N1 0.3 (3) Cl5 Cd3 Cl4 Cd (18) C8 N3 C5 C6 0.2 (4) Cl9 Cd3 Cl4 Cd (16) N3 C5 C6 C7 0.8 (4) Cl6 Cd3 Cl4 Cd (15) C8 N4 C7 C6 0.4 (4) Cl10 Cd2 Cl4 Cd (18) C5 C6 C7 N4 0.7 (4) Cl6 Cd2 Cl4 Cd (16) C5 N3 C8 O (2) Cl3 Cd2 Cl4 Cd (17) C5 N3 C8 N4 1.2 (3) Cl9 Cd2 Cl4 Cd (18) C7 N4 C8 O (2) Cl10 Cd2 Cl4 Cd (18) C7 N4 C8 N3 1.3 (3) Cl6 Cd2 Cl4 Cd (16) C12 N6 C9 C (4) Cl3 Cd2 Cl4 Cd (18) N6 C9 C10 C (4) Cl9 Cd2 Cl4 Cd (16) C12 N5 C11 C (4) Cl8 Cd3 Cl5 Cd (19) C9 C10 C11 N5 1.0 (4) Cl7 Cd3 Cl5 Cd (19) O3 O3 C12 N5 0.0 (7) Cl9 Cd3 Cl5 Cd (6) O3 O3 C12 N6 0.0 (6) Cl4 Cd3 Cl5 Cd (17) C11 N5 C12 O (2) Cl6 Cd3 Cl5 Cd (17) C11 N5 C12 O (2) Cl2 Cd1 Cl5 Cd (19) C11 N5 C12 N6 1.4 (3) Cl1 Cd1 Cl5 Cd (19) C9 N6 C12 O (3) Cl3 Cd1 Cl5 Cd (5) C9 N6 C12 O (3) Cl4 Cd1 Cl5 Cd (17) C9 N6 C12 N5 1.5 (3) Cl6 Cd1 Cl5 Cd (17) C16 N7 C13 C (4) Cl11 Cd2 Cl6 Cd (17) N7 C13 C14 C (4) Cl3 Cd2 Cl6 Cd (18) C16 N8 C15 C (5) Cl9 Cd2 Cl6 Cd (16) C13 C14 C15 N8 5.8 (4) Cl4 Cd2 Cl6 Cd (16) C15 N8 C16 O (3) Cl11 Cd2 Cl6 Cd (17) C15 N8 C16 N7 4.8 (5) Cl3 Cd2 Cl6 Cd (17) C13 N7 C16 O (3) Cl9 Cd2 Cl6 Cd (18) C13 N7 C16 N8 7.2 (4) Cl4 Cd2 Cl6 Cd (16) C20 N9 C17 C (4) Cl8 Cd3 Cl6 Cd (18) N9 C17 C18 C (4) Cl5 Cd3 Cl6 Cd (18) C20 N10 C19 C (4) Cl9 Cd3 Cl6 Cd (17) C17 C18 C19 N (4) Cl4 Cd3 Cl6 Cd (16) C19 N10 C20 O (3) Cl8 Cd3 Cl6 Cd (18) C19 N10 C20 N9 3.0 (4) Cl5 Cd3 Cl6 Cd (17) C17 N9 C20 O (3) Cl9 Cd3 Cl6 Cd (18) C17 N9 C20 N (4) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A N2 H2A Cl11 i (2) 138 N3 H3A Cl8 ii (2) 144 N4 H4A Cl10 iii (2) 169 N5 H5A Cl7 iv (2) 151 sup-9

13 N6 H6A Cl1 v (2) 162 N7 H7A O2 vi (3) 167 N10 H10B Cl7 vi (2) 157 N8 H8A O5 vii (3) 120 N8 H8A O4 viii (4) 150 N9 H9B O (3) 152 Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x, y+1, z; (iv) x+1, y+1, z+1; (v) x, y+1/2, z+1/2; (vi) x, y, z+1; (vii) x+1, y+1, z+2; (viii) x+1, y+2, z+2. sup-10

14 Fig. 1 sup-11

15 Fig. 2 sup-12

16 Fig. 3 sup-13