electronic reprint Tetraaquabis(thiourea-κS)cadmium(II) triaquatris(thiourea-κs)cadmium(ii) disulfate
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1 ISSN Inorgani c compounds Metal-orga nic compounds Organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Editors: W.T. A. Harrison, H. Stoeckli-Evans, E. R.T. Tiekink and M. Weil Tetraaquabis(thiourea-κS)cadmium(II) triaquatris(thiourea-κs)cadmium(ii) disulfate Masood Parvez, Farideh Jalilehvand and Zahra Amini This open-access article is distributed under the terms of the Creative Commons Attribution Licence which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. Volume 61 Part 11 November 2005 Acta Crystallographica Section E Structure Reports Online Editors: W. Clegg and D. G. Watson Acta Crystallographica Section E: Structure Reports Online is the IUCr s highly popular open-access structural journal. It provides a simple and easily accessible publication mechanism for the growing number of inorganic, metal-organic and organic crystal structure determinations. The electronic submission, validation, refereeing and publication facilities of the journal ensure very rapid and high-quality publication, whilst key indicators and validation reports provide measures of structural reliability. The journal publishes over 4000 structures per year. The average publication time is less than one month. journals.iucr.org International Union of Crystallography * Chester Crystallography Journals Online is available from journals.iucr.org Parvez et al. [Cd(CH 4 N 2 S) 2 (H 2 O) 4 ][Cd(CH 4 N 2 S) 3 (H 2 O) 3 ](SO 4 ) 2
2 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Tetraaquabis(thiourea-jS)cadmium(II) triaquatris(thiourea-js)cadmium(ii) disulfate Masood Parvez, Farideh Jalilehvand* and Zahra Amini Department of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4 Correspondence faridehj@ucalgary.ca a = (3) Å b = (3) A c = (5) Å f = (12) 0 V = (13) Å 3 Data collection Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1997) T min = 0.876, T max = Refinement R[F 2 >2a(F 2 )] = wr(f 2 ) = S = reflections 453 parameters Z = 4 Mo Ka radiation f = 1.94 mm -1 T = 173 K 0.07 x 0.06 x 0.05 mm measured reflections 9995 independent reflections 8817 reflections with I > 2a(I) R int = restraints H-atom parameters constrained -3!p max = 0.78 e A!p min = e A -3 Received 18 May 2012; accepted 12 June 2012 Key indicators: single-crystal X-ray study; T = 173 K; mean a(n C) = Å; disorder in solvent or counterion; R factor = 0.047; wr factor = 0.099; data-toparameter ratio = Table 1 Hydrogen-bond geometry (Å, 0 ). D H---A D H H---A D---A D H---A The title compound, [Cd(CH 4 N 2 S) 2 (H 2 O) 4 ][Cd(CH 4 N 2 S) 3 (H 2 O) 3 ](SO 4 ) 2, contains two molecules of each of the Cd complexes and four sulfate ions in the asymmetric unit: all the Cd atoms exhibit distorted octahedral geometries. The Cd S and Cd O bond lengths around the Cd atoms in the bis(thiourea) cations are in the ranges (4) (4) and (8) (9) Å, respectively, and the S atoms are in a cis orientation. In the tris(thiourea) cations, the corresponding bond lengths around the Cd atoms are slightly longer and are in the ranges (4) (3) and (7) (10) A, respectively, and the S atoms are in a fac disposition. The crystal structure features numerous N H---O, N H---N, O H---O and O H---N hydrogen bonds. Two O atoms of a sulfate anion were found to be disordered over two orientations in a (9):0.380 (9) ratio. The crystal studied was a racemic twin with BASF = 0.17 (5) Related literature For the structures of other cadmium sulfate thiourea compounds, see: Cavaica et al. (1970); Corao & Baggio (1969); Oussaid et al. (2000). For the NMR measurement, see: Jalilehvand et al. (2012). Experimental Crystal data [Cd(CH 4 N 2 S) 2 (H 2 O) 4 ]- M r = [Cd(CH 4 N 2 S) 3 (H 2 O) 3 ](SO 4 ) 2 Monoclinic, Pc N1 H1A---O26 i 0.88 N1 H1A---O26 0i 0.88 N1 H1B---O17 i 0.88 N1 H1B---O15 i 0.88 N2 H2A---O24 i 0.88 N2 H2B---O N3 H3A---O N4 H4A---O N4 H4B---O N4 H4B---O O1 H11---O29 ii 0.82 O1 H12---O O2 H21---O26 ii 0.82 O2 H21---O26 0ii 0.82 O3 H32---O18 ii 0.82 O4 H41---O15 ii 0.82 O4 H42---O29 ii 0.81 N5 H5A---O24 i 0.88 N6 H6A---O23 i 0.88 N6 H6B---O N6 H6B---O N7 H7A---O N7 H7B---O N8 H8A---O N8 H8B---O N8 H8B---O19 iii 0.88 O5 H52---O O5 H51---N O6 H62---O30 iv 0.83 O7 H72---O22 v 0.82 O8 H81---O16 iv 0.83 O8 H82---O N9 H9A---O N9 H9A---O N9 H9B---O N10 H10A---O N10 H10B---O N11 H11A---O18 i 0.88 N11 H11B---O N12 H12A---O17 i 0.88 N13 H13A---O N13 H13B---O28 iv 0.88 N14 H14A---O26 i 0.88 O9 H91---O28 iv 0.82 O9 H92---O20 iv 0.82 O9 H92---O22 iv 0.82 O10 H101---O O10 H102---O25 0iv 0.82 O10 H102---O25 iv 0.82 O11 H111---O25 iv 0.82 O11 H111---O26 0iv (16) (2) (15) (14) (15) (14) (14) (13) (12) (12) (13) (12) (12) (18) (10) (13) (12) (11) (11) (12) (12) (17) (14) (15) (15) (14) (13) (14) (11) (11) (12) (13) (17) (16) (17) (17) (15) (12) (12) (12) (11) (13) (13) (12) (11) (10) (11) (2) (13) (14) (18) 163 doi: /s Parvez et al. m949
3 metal-organic compounds D H---A D H H---A D---A D H---A O11 H112---O29 iv (13) 153 N15 H15A---O (12) 148 N15 H15A---N (15) 131 N16 H16A---O6 vi (11) 161 N16 H16B---O23 ii (11) 172 N17 H17A---O21 iii (13) 176 N18 H18A---O22 iii (12) 169 N18 H18B---O (11) 163 N19 H19A---O17 vii (15) 145 N19 H19A---O16 vii (15) 156 N19 H19B---O24 i (15) 163 N19 H19B---O25 0i (2) 129 N20 H20A---O17 vii (16) 153 N20 H20B---O (15) 165 O12 H121---O23 ii (10) 167 O12 H122---O16 viii (9) 140 O13 H131---O19 ii (12) 171 O13 H132---O4 iii (12) 153 O14 H141---O20 ii (11) 173 O14 H142---O25 ii (14) 135 O14 H142---O25 0ii (2) 161 Symmetry codes: (i) x þ 1; -y þ 1; z - 1 2; (ii) x; -y þ 1; z - 1 2; (iii) x; y þ 1; z; (iv) x þ 1; y; z; (v) x þ 1; y þ 1; z; (vi) x - 1; y; z; (vii) x þ 1; -y þ 2; z - 1 2; (viii) x; -y þ 2; z Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALE PACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97. This research was supported by the National Science and Engineering Research Council (NSERC) of Canada, the Canadian Foundation for Innovation (CFI) and the Province of Alberta (Department of Innovation and Science). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6807). References Blessing, R. H. (1997). J. Appl. Cryst. 30, Cavaica, L., Villa, A. C., Mangia, A. & Palmeiri, C. (1970). Inorg. Chim. Acta, 4, Corao, E. & Baggio, S. (1969). Inorg. Chim. Acta, 3, Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands. Jalilehvand, F., Amini, Z. & Parmar, K. (2012). Inorg. Chem. Submitted. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp New York: Academic Press. Oussaid, M., Becker, P. & Carabatos-Né delec, C. (2000). J. Raman Spectrosc. 31, Sheldrick, G. M. (2008). Acta Cryst. A64, m950 Parvez et al. [Cd(CH 4 N 2 S) 2 (H 2 O) 4 ][Cd(CH 4 N 2 S) 3 (H 2 O) 3 ](SO 4 ) 2
4 supplementary materials [doi: /s ] Tetraaquabis(thiourea-κS)cadmium(II) triaquatris(thiourea-κs)cadmium(ii) disulfate Masood Parvez, Farideh Jalilehvand and Zahra Amini Comment A survey in the crystal structure database shows that mixing cadmium sulfate (CdSO 4 ) with thiourea (TU) in the mole ratio 1:3 results in either monomeric [Cd(TU) 3 (SO 4 )] (Oussaid et al., 2000; Cavaica et al., 1970), (or dimeric [Cd(µ-TU) (TU) 2 (SO 4 )] 2 complexes (Corao & Baggio, 1969) with the cadmium ion coordinating four (CdS 3 O) or five (CdS 4 O) ligand atoms, respectively. With intention to prepare the mononuclear [Cd(TU) 3 (SO 4 )] complex for a solid state 113 Cd NMR measurement (Jalilehvand et al., 2012), a solution was prepared of a mixture of CdSO 4. 8/3H 2 O and thiourea in 1:3.8 mole ratio in hot water, and slowly evaporated resulting in colorless crystals. Elemental analysis of a ground sample (i) used for the solid state 113 Cd NMR spectroscopy showed that the bulk of the crystalline solid mainly consisted of the [Cd(TU) 3 (SO 4 )] complex (see Special details section). However, elemental analyses of two random samples of the colorless crystals (ii and iii) showed that the sample was inhomogeneous. An X-ray crystallographic structure determination of the colorless crystal, revealed that cis-[cd(tu) 2 (H 2 O) 4 ] 2+ and fac-[cd(tu) 3 (H 2 O) 3 ] 2+ complexes had co-crystallized in the crystal. To our knowledge, this is the first report on the structure of hydrated Cd(II) thiourea complexes. The asymmetric unit of the title co-crystal contains two cadmium(ii) complexes of each type together with four sulfate ions (Fig. 1). All Cd atoms exhibit distorted octahedral geometry. The Cd S and Cd O distances around Cd1 and Cd2 atoms in the bis(thiourea) complex, cis-[cd(tu) 2 (H 2 O) 4 ] 2+, lie in the ranges (4) (4) Å and (8) (9) Å, respectively. In the tris(thiourea) complex, fac-[cd(tu) 3 (H 2 O) 3 ] 2+, the corresponding bond lengths around Cd3 and Cd4 atoms are slightly longer and lie in the ranges (4) (3) Å and (7) (10) Å, respectively. The crystal structure is stabilized by strong hydrogen bonds (Tab. 1). Experimental A colorless solution containing a mixture of CdSO 4. 8/3(H 2 O) (1.505 g, 5.87 mmol) and thiourea (1.340 g, mmol) in hot water (10 ml) was prepared. Slow evaporation of this solution resulted in an inhomogeneous mixture of colorless crystals, mainly consisting of [Cd(TU) 3 (SO 4 )] complex, as well as cis-[cd(tu) 2 (H 2 O) 4 ](SO 4 ) and fac-[cd(tu) 3 (H 2 O) 3 ] (SO 4 ) complexes that were co-crystallized in the same unit cell. Refinement All H atoms were positioned geometrically and refined using a riding model, and the U iso (H) were allowed at 1.2U eq (parent atom). Water H-atoms were contrained at distances O H = 0.82 Å and EADP commands were used to model the disorder. An absolute structure using Flack method was not determined as the crystals were composed of racemic twins with BASF = 0.17 (5); Fridel pairs were merged. Two oxygen atoms of a sulfate anion were disordered over two sites each in a ratio (9):0.380 (9). A refinement of the structure with half the current length of the cell sup-1
5 axis-b, allowing half of the contents of the unit cell, resulted in a grossly disordered model which was therefore ruled out as the unit cell. Therefore, the model was refined in the current supercell presented in this paper. Computing details Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008). Figure 1 The molecular structure of the contents of an asymmetric unit of the title compound with displacement ellipsoids drawn at the 30% probability level. sup-2
6 Figure 2 The content of a unit cell. For the cadmium complexes in the left part of the cell only the sulfur atoms are shown for clarity. Tetraaquabis(thiourea-κS)cadmium(II) triaquatris(thiourea-κs)cadmium(ii) disulfate Crystal data [Cd(CH 4 N 2 S) 2 (H 2 O) 4 ][Cd(CH 4 N 2 S) 3 (H 2 O) 3 ] Z = 4 (SO 4 ) 2 F(000) = 1848 M r = D x = Mg m 3 Monoclinic, Pc Mo Kα radiation, λ = Å Hall symbol: P -2yc Cell parameters from 2175 reflections a = (3) Å θ = b = (3) Å µ = 1.94 mm 1 c = (5) Å T = 173 K β = (12) Prism, colorless V = (13) Å mm Data collection Nonius KappaCCD measured reflections diffractometer 9995 independent reflections Radiation source: fine-focus sealed tube 8817 reflections with I > 2σ(I) Graphite monochromator R int = ω and φ scans θ max = 25.0, θ min = 2.4 Absorption correction: multi-scan h = (SORTAV; Blessing, 1997) k = T min = 0.876, T max = l = Refinement Refinement on F 2 Primary atom site location: structure-invariant Least-squares matrix: full direct methods R[F 2 > 2σ(F 2 )] = Secondary atom site location: difference Fourier wr(f 2 ) = map S = 1.08 Hydrogen site location: inferred from 9995 reflections neighbouring sites 453 parameters H-atom parameters constrained 2 restraints w = 1/[σ 2 (F 2 o ) + (0.0102P) P] 2 where P = (F o + 2F 2 c )/3 sup-3
7 (Δ/σ) max = Absolute structure: Flack, H. D. (1983). Acta Δρ max = 0.78 e Å 3 Cryst. A39, Δρ min = 0.64 e Å 3 Flack parameter: 0.15 (5) Special details Experimental. Elemental analysis of a ground sample (i) used for the solid state 113 Cd NMR spectroscopy: C = 8.44%, H = 2.62%, N = 19.27% (calculated for [Cd(TU) 3 (SO 4 )]: CdC 3 H 12 N 6 O 4 S 4 (M.W. = 436.7), C = 8.24%, H = 2.75%, N = 19.23%). Elemental analyses of two random samples of the colorless crystals: (ii) exp.: C = 8.23%, H = 2.68%, N = 19.08%, and (iii) exp.: C = 7.44%, H = 3.01%, N = 17.22% (calculated for [Cd(TU) 3 (H 2 O) 3 ](SO 4 ): CdC 3 H 18 N 6 O 7 S 4 (M.W. = 490.7), C = 7.33%, H = 3.67%, N = 17.12%). 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. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x Cd (7) S (4) S (3) C (13) C (9) N (12) H1A H1B N (11) H2A H2B N (8) H3A H3B N (8) H4A H4B O (8) H H O (7) H H O (7) H H O (9) H H Cd (7) S (3) S (4) C (10) y z (8) (3) (3) (17) (3) (14) (12) (5) (8) (4) (10) (5) (11) (5) (8) (4) (8) (4) (8) (4) (6) (3) (6) (3) (7) (4) (9) (3) (3) (14) (3) (17) (9) (4) U iso */U eq (3) (9) (6) (17) (17) (12) 0.031* 0.031* (12) 0.031* 0.031* (12) 0.031* 0.031* (12) 0.031* 0.031* (9) 0.027* 0.027* (9) 0.027* 0.027* (9) 0.027* 0.027* (9) 0.027* 0.027* (3) (6) (9) (2) Occ. (<1) sup-4
8 C (13) (12) (5) (2) N (8) (7) (4) (11) H5A * H5B * N (8) (7) (4) (11) H6A * H6B * N (10) (11) (5) (11) H7A * H7B * N (12) (10) (5) (11) H8A * H8B * O (8) (8) (4) (10) H * H * O (7) (7) (3) (10) H * H * O (7) (6) (3) (10) H * H * O (10) (8) (4) (10) H * H * Cd (7) (8) (3) (3) S (4) (3) (17) (8) S (3) (3) (14) (6) S (3) (2) (14) (6) C (14) (12) (6) (14) C (10) (9) (4) (14) C (10) (9) (4) (14) N (12) (12) (5) (10) H9A * H9B * N (11) (12) (5) (10) H10A * H10B * N (9) (8) (4) (10) H11A * H11B * N (9) (9) (4) (10) H12A * H12B * N (9) (8) (4) (10) H13A * H13B * N (9) (9) (4) (10) H14A * sup-5
9 H14B * O (7) (6) (3) (10) H * H * O (7) (7) (4) (10) H * H * O (9) (8) (4) (10) H * H * Cd (7) (8) (3) (3) S (3) (2) (13) (6) S (3) (2) (14) (6) S (4) (3) (18) (9) C (10) (8) (4) (14) C (10) (8) (4) (14) C (15) (12) (6) (14) N (9) (8) (4) (9) H15A * H15B * N (9) (7) (4) (9) H16A * H16B * N (9) (8) (4) (9) H17A * H17B * N (8) (7) (4) (9) H18A * H18B * N (12) (10) (5) (9) H19A * H19B * N (11) (10) (5) (9) H20A * H20B * O (7) (6) (3) (10) H * H * O (7) (7) (3) (10) H * H * O (9) (7) (4) (10) H * H * S (4) (3) (15) (8) O (7) (6) (3) (9) O (6) (6) (3) (9) O (8) (7) (3) (9) O (7) (6) (3) (9) sup-6
10 S (4) (3) (15) (8) O (8) (7) (4) (11) O (8) (7) (3) (11) O (9) (8) (4) (11) O (8) (7) (4) (11) S (3) (3) (15) (8) O (7) (6) (3) (9) O (8) (7) (3) (9) O (9) (9) (4) (9) (9) O (9) (9) (4) (9) (9) O (16) (16) (7) (9) (9) O (15) (14) (7) (9) (9) S (4) (3) (17) (8) O (10) (9) (5) (11) O (8) (7) (4) (11) O (8) (7) (4) (11) O (8) (7) (4) (11) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Cd (6) (5) (5) (4) (5) (4) S (19) (16) (2) (13) (15) (13) S (13) (18) (13) (13) (11) (13) C (4) (4) (3) (3) (3) (3) C (4) (4) (3) (3) (3) (3) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) O (2) (2) (2) (17) (17) (17) O (2) (2) (2) (17) (17) (17) O (2) (2) (2) (17) (17) (17) O (2) (2) (2) (17) (17) (17) Cd (6) (5) (5) (4) (4) (4) S (14) (19) (13) (13) (11) (13) S (2) (16) (18) (14) (15) (13) C (6) (6) (5) (5) (4) (4) C (5) (5) (4) (4) (4) (4) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) N (3) (3) (3) (2) (2) (2) O (2) (2) (2) (18) (18) (18) O (2) (2) (2) (18) (18) (18) O (2) (2) (2) (18) (18) (18) O (2) (2) (2) (18) (18) (18) Cd (6) (5) (6) (4) (4) (4) S (19) (15) (18) (13) (14) (12) S (15) (16) (13) (12) (11) (11) sup-7
11 S (14) (14) (13) (11) (11) (11) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) N (2) (3) (2) (2) (17) (18) N (2) (3) (2) (2) (17) (18) N (2) (3) (2) (2) (17) (18) N (2) (3) (2) (2) (17) (18) N (2) (3) (2) (2) (17) (18) N (2) (3) (2) (2) (17) (18) O (2) (2) (2) (19) (18) (19) O (2) (2) (2) (19) (18) (19) O (2) (2) (2) (19) (18) (19) Cd (6) (5) (5) (4) (4) (4) S (14) (14) (13) (11) (11) (11) S (14) (15) (12) (11) (10) (11) S (2) (16) (19) (13) (15) (13) C (4) (3) (3) (3) (3) (3) C (4) (3) (3) (3) (3) (3) C (4) (3) (3) (3) (3) (3) N (2) (2) (2) (18) (17) (17) N (2) (2) (2) (18) (17) (17) N (2) (2) (2) (18) (17) (17) N (2) (2) (2) (18) (17) (17) N (2) (2) (2) (18) (17) (17) N (2) (2) (2) (18) (17) (17) O (2) (2) (2) (2) (18) (18) O (2) (2) (2) (2) (18) (18) O (2) (2) (2) (2) (18) (18) S (18) (15) (16) (13) (13) (12) O (2) (2) (17) (16) (15) (15) O (2) (2) (17) (16) (15) (15) O (2) (2) (17) (16) (15) (15) O (2) (2) (17) (16) (15) (15) S (17) (15) (17) (13) (13) (13) O (2) (2) (2) (18) (18) (19) O (2) (2) (2) (18) (18) (19) O (2) (2) (2) (18) (18) (19) O (2) (2) (2) (18) (18) (19) S (17) (16) (15) (12) (12) (12) O (2) (2) (19) (17) (16) (16) O (2) (2) (19) (17) (16) (16) O (2) (2) (19) (17) (16) (16) O (2) (2) (19) (17) (16) (16) O (2) (2) (19) (17) (16) (16) O (2) (2) (19) (17) (16) (16) S (19) (16) (18) (14) (14) (13) O (3) (3) (3) (2) (2) (2) O (3) (3) (3) (2) (2) (2) sup-8
12 O (3) (3) (3) (2) (2) (2) O (3) (3) (3) (2) (2) (2) Geometric parameters (Å, º) Cd1 O (7) C7 N (13) Cd1 O (7) N9 H9A Cd1 O (10) N9 H9B Cd1 O (9) N10 H10A Cd1 S (4) N10 H10B Cd1 S (4) N11 H11A S1 C (16) N11 H11B S2 C (9) N12 H12A C1 N (18) N12 H12B C1 N (2) N13 H13A C2 N (13) N13 H13B C2 N (12) N14 H14A N1 H1A N14 H14B N1 H1B O9 H N2 H2A O9 H N2 H2B O10 H N3 H3A O10 H N3 H3B O11 H N4 H4A O11 H N4 H4B Cd4 O (7) O1 H Cd4 O (9) O1 H Cd4 O (9) O2 H Cd4 S (4) O2 H Cd4 S (3) O3 H Cd4 S (3) O3 H S8 C (10) O4 H S9 C (10) O4 H S10 C (15) Cd2 O (11) C8 N (14) Cd2 O (8) C8 N (14) Cd2 O (8) C9 N (13) Cd2 O (10) C9 N (13) Cd2 S (4) C10 N (18) Cd2 S (4) C10 N (2) S3 C (11) N15 H15A S4 C (15) N15 H15B C3 N (13) N16 H16A C3 N (13) N16 H16B C4 N (19) N17 H17A C4 N (18) N17 H17B N5 H5A N18 H18A N5 H5B N18 H18B N6 H6A N19 H19A N6 H6B N19 H19B N7 H7A N20 H20A sup-9
13 N7 H7B N20 H20B N8 H8A O12 H N8 H8B O12 H O5 H O13 H O5 H O13 H O6 H O14 H O6 H O14 H O7 H S11 O (8) O7 H S11 O (8) O8 H S11 O (9) O8 H S11 O (8) Cd3 O (8) S12 O (10) Cd3 O (9) S12 O (11) Cd3 O (10) S12 O (9) Cd3 S (4) S12 O (9) Cd3 S (3) S13 O (17) Cd3 S (3) S13 O (10) S5 C (15) S13 O (9) S6 C (10) S13 O (8) S7 C (10) S13 O (11) C5 N (2) S13 O (18) C5 N (2) S14 O (10) C6 N (13) S14 O (11) C6 N (13) S14 O (10) C7 N (14) S14 O (9) O2 Cd1 O (3) N11 C6 S (8) O2 Cd1 O (3) N13 C7 N (9) O3 Cd1 O (3) N13 C7 S (8) O2 Cd1 O (3) N14 C7 S (8) O3 Cd1 O (3) C5 N9 H9A O4 Cd1 O (3) C5 N9 H9B O2 Cd1 S (2) H9A N9 H9B O3 Cd1 S (2) C5 N10 H10A O4 Cd1 S (3) C5 N10 H10B O1 Cd1 S (2) H10A N10 H10B O2 Cd1 S (2) C6 N11 H11A O3 Cd1 S (2) C6 N11 H11B O4 Cd1 S (2) H11A N11 H11B O1 Cd1 S (2) C6 N12 H12A S1 Cd1 S (13) C6 N12 H12B C1 S1 Cd (4) H12A N12 H12B C2 S2 Cd (4) C7 N13 H13A N2 C1 N (14) C7 N13 H13B N2 C1 S (11) H13A N13 H13B N1 C1 S (11) C7 N14 H14A N4 C2 N (9) C7 N14 H14B N4 C2 S (8) H14A N14 H14B N3 C2 S (8) Cd3 O9 H sup-10
14 C1 N1 H1A Cd3 O9 H C1 N1 H1B H91 O9 H H1A N1 H1B Cd3 O10 H C1 N2 H2A H101 O10 H C1 N2 H2B Cd3 O11 H H2A N2 H2B Cd3 O11 H C2 N3 H3A H111 O11 H C2 N3 H3B O12 Cd4 O (3) H3A N3 H3B O12 Cd4 O (3) C2 N4 H4A O14 Cd4 O (3) C2 N4 H4B O12 Cd4 S (2) H4A N4 H4B O14 Cd4 S (2) Cd1 O1 H O13 Cd4 S (2) Cd1 O1 H O12 Cd4 S (19) H11 O1 H O14 Cd4 S (2) Cd1 O2 H O13 Cd4 S (2) H21 O2 H S10 Cd4 S (13) Cd1 O3 H O12 Cd4 S (19) Cd1 O3 H O14 Cd4 S (2) H31 O3 H O13 Cd4 S (2) Cd1 O4 H S10 Cd4 S (12) Cd1 O4 H S9 Cd4 S (11) H41 O4 H C8 S8 Cd (3) O8 Cd2 O (3) C9 S9 Cd (4) O8 Cd2 O (3) C10 S10 Cd (5) O6 Cd2 O (3) N15 C8 N (9) O8 Cd2 O (3) N15 C8 S (8) O6 Cd2 O (3) N16 C8 S (8) O7 Cd2 O (3) N18 C9 N (9) O8 Cd2 S (3) N18 C9 S (8) O6 Cd2 S (2) N17 C9 S (8) O7 Cd2 S (2) N20 C10 N (14) O5 Cd2 S (2) N20 C10 S (12) O8 Cd2 S (2) N19 C10 S (11) O6 Cd2 S (2) C8 N15 H15A O7 Cd2 S (2) C8 N15 H15B O5 Cd2 S (2) H15A N15 H15B S4 Cd2 S (13) C8 N16 H16A C3 S3 Cd (4) C8 N16 H16B C4 S4 Cd (4) H16A N16 H16B N5 C3 N (10) C9 N17 H17A N5 C3 S (8) C9 N17 H17B N6 C3 S (8) H17A N17 H17B N8 C4 N (13) C9 N18 H18A N8 C4 S (11) C9 N18 H18B N7 C4 S (11) H18A N18 H18B C3 N5 H5A C10 N19 H19A C3 N5 H5B C10 N19 H19B H5A N5 H5B H19A N19 H19B sup-11
15 C3 N6 H6A C10 N20 H20A C3 N6 H6B C10 N20 H20B H6A N6 H6B H20A N20 H20B C4 N7 H7A Cd4 O12 H C4 N7 H7B H121 O12 H H7A N7 H7B Cd4 O13 H C4 N8 H8A Cd4 O13 H C4 N8 H8B H131 O13 H H8A N8 H8B Cd4 O14 H Cd2 O5 H Cd4 O14 H Cd2 O5 H H141 O14 H H51 O5 H O16 S11 O (5) Cd2 O6 H O16 S11 O (5) Cd2 O6 H O18 S11 O (5) H61 O6 H O16 S11 O (4) Cd2 O7 H O18 S11 O (4) H71 O7 H O17 S11 O (5) Cd2 O8 H O19 S12 O (6) H81 O8 H O19 S12 O (5) O9 Cd3 O (3) O21 S12 O (6) O9 Cd3 O (3) O19 S12 O (5) O10 Cd3 O (3) O21 S12 O (6) O9 Cd3 S (2) O22 S12 O (5) O10 Cd3 S (2) O26 S13 O (8) O11 Cd3 S (3) O26 S13 O (8) O9 Cd3 S (2) O25 S13 O (6) O10 Cd3 S (2) O26 S13 O (8) O11 Cd3 S (2) O25 S13 O (5) S5 Cd3 S (13) O24 S13 O (5) O9 Cd3 S (2) O25 S13 O (6) O10 Cd3 S (2) O24 S13 O (5) O11 Cd3 S (2) O23 S13 O (5) S5 Cd3 S (12) O26 S13 O (9) S6 Cd3 S (12) O24 S13 O (7) C5 S5 Cd (5) O23 S13 O (7) C6 S6 Cd (4) O26 S13 O (8) C7 S7 Cd (4) O29 S14 O (6) N10 C5 N (14) O29 S14 O (6) N10 C5 S (11) O27 S14 O (6) N9 C5 S (11) O29 S14 O (5) N12 C6 N (10) O27 S14 O (6) N12 C6 S (8) O28 S14 O (6) O2 Cd1 S1 C (11) O9 Cd3 S6 C (4) O3 Cd1 S1 C (5) O10 Cd3 S6 C (4) O4 Cd1 S1 C (6) S5 Cd3 S6 C (4) O1 Cd1 S1 C (6) S7 Cd3 S6 C (4) S2 Cd1 S1 C (5) O9 Cd3 S7 C (4) O2 Cd1 S2 C (4) O11 Cd3 S7 C (5) sup-12
16 O3 Cd1 S2 C (4) S5 Cd3 S7 C (4) O4 Cd1 S2 C (8) S6 Cd3 S7 C (4) O1 Cd1 S2 C (5) Cd3 S5 C5 N (12) S1 Cd1 S2 C (4) Cd3 S5 C5 N (10) Cd1 S1 C1 N (12) Cd3 S6 C6 N (8) Cd1 S1 C1 N (10) Cd3 S6 C6 N (10) Cd1 S2 C2 N (10) Cd3 S7 C7 N (9) Cd1 S2 C2 N (7) Cd3 S7 C7 N (9) O8 Cd2 S3 C (8) O12 Cd4 S8 C (5) O6 Cd2 S3 C (4) O14 Cd4 S8 C (5) O7 Cd2 S3 C (4) S10 Cd4 S8 C (4) O5 Cd2 S3 C (5) S9 Cd4 S8 C (4) S4 Cd2 S3 C (4) O12 Cd4 S9 C (4) O8 Cd2 S4 C (6) O13 Cd4 S9 C (4) O6 Cd2 S4 C (11) S10 Cd4 S9 C (4) O7 Cd2 S4 C (5) S8 Cd4 S9 C (4) O5 Cd2 S4 C (5) O12 Cd4 S10 C (8) S3 Cd2 S4 C (5) O14 Cd4 S10 C (6) Cd2 S3 C3 N (8) O13 Cd4 S10 C (6) Cd2 S3 C3 N (10) S9 Cd4 S10 C (6) Cd2 S4 C4 N (10) S8 Cd4 S10 C (6) Cd2 S4 C4 N (11) Cd4 S8 C8 N (8) O9 Cd3 S5 C (7) Cd4 S8 C8 N (8) O10 Cd3 S5 C (6) Cd4 S9 C9 N (9) O11 Cd3 S5 C (6) Cd4 S9 C9 N (7) S6 Cd3 S5 C (5) Cd4 S10 C10 N (13) S7 Cd3 S5 C (5) Cd4 S10 C10 N (10) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A N1 H1A O26 i (16) 154 N1 H1A O26 i (2) 168 N1 H1B O17 i (15) 156 N1 H1B O15 i (14) 122 N2 H2A O24 i (15) 163 N2 H2B O (14) 165 N3 H3A O (14) 169 N4 H4A O (13) 157 N4 H4B O (12) 155 N4 H4B O (12) 121 O1 H11 O29 ii (13) 160 O1 H12 O (12) 164 O2 H21 O26 ii (12) 128 O2 H21 O26 ii (18) 150 O3 H32 O18 ii (10) 156 O4 H41 O15 ii (13) 172 O4 H42 O29 ii (12) 173 N5 H5A O24 i (11) 171 sup-13
17 N6 H6A O23 i (11) 162 N6 H6B O (12) 153 N6 H6B O (12) 123 N7 H7A O (17) 165 N7 H7B O (14) 163 N8 H8A O (15) 162 N8 H8B O21 iii (15) 159 N8 H8B O19 iii (14) 124 O5 H52 O (13) 164 O5 H51 N (14) 114 O6 H62 O30 iv (11) 162 O7 H72 O22 v (11) 155 O8 H81 O16 iv (12) 162 O8 H82 O10 iii (13) 152 N9 H9A O (17) 143 N9 H9A O (16) 156 N9 H9B O (17) 164 N10 H10A O (17) 148 N10 H10B O (15) 163 N11 H11A O18 i (12) 177 N11 H11B O (12) 167 N12 H12A O17 i (12) 169 N13 H13A O2 iv (11) 158 N13 H13B O28 iv (13) 168 N14 H14A O26 i (13) 145 O9 H91 O28 iv (12) 159 O9 H92 O20 iv (11) 159 O9 H92 O22 iv (10) 137 O10 H101 O (11) 139 O10 H102 O25 iv (2) 164 O10 H102 O25 iv (13) 156 O11 H111 O25 iv (14) 143 O11 H111 O26 iv (18) 163 O11 H112 O29 iv (13) 153 N15 H15A O (12) 148 N15 H15A N (15) 131 N16 H16A O6 vi (11) 161 N16 H16B O23 ii (11) 172 N17 H17A O21 iii (13) 176 N18 H18A O22 iii (12) 169 N18 H18B O (11) 163 N19 H19A O17 vii (15) 145 N19 H19A O16 vii (15) 156 N19 H19B O24 i (15) 163 N19 H19B O25 i (2) 129 N20 H20A O17 vii (16) 153 N20 H20B O (15) 165 O12 H121 O23 ii (10) 167 O12 H122 O16 viii (9) 140 sup-14
18 O13 H131 O19 ii (12) 171 O13 H132 O4 iii (12) 153 O14 H141 O20 ii (11) 173 O14 H142 O25 ii (14) 135 O14 H142 O25 ii (2) 161 Symmetry codes: (i) x+1, y+1, z 1/2; (ii) x, y+1, z 1/2; (iii) x, y+1, z; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) x 1, y, z; (vii) x+1, y+2, z 1/2; (viii) x, y+2, z 1/2. sup-15
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