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ISSN: 2056-9890

Unexpected reactions of NHC*—CuI and —AgI bromides with potassium thio- or seleno­cyanate

aSchool of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland
*Correspondence e-mail: helge.muellerbunz@ucd.ie

Edited by M. Weil, Vienna University of Technology, Austria (Received 22 August 2019; accepted 8 October 2019; online 22 October 2019)

The reactions of N-heterocyclic carbene CuI and AgI halides with potassium thio- or seleno­cyanate gave unexpected products. The attempted substitution reaction of bromido­(1,3-dibenzyl-4,5-di­phenyl­imidazol-2-yl­idene)silver (NHC*—Ag—Br) with KSCN yielded bis­[bis­(1,3-dibenzyl-4,5-di­phenyl­imidazol-2-yl­idene)silver(I)] tris­(thio­cyanato)­argentate(I) diethyl ether disolvate, [Ag(C29H24N2)2][Ag(NCS)3]·2C4H10O or [NHC*2Ag]2[Ag(SCN)3]·2Et2O, (1), while reaction with KSeCN led to bis­(μ-1,3-dibenzyl-4,5-diphenyl-2-seleno­imidazole-κ2Se:Se)bis­[bromido­(1,3-dibenzyl-4,5-diphenyl-2-seleno­imid­azole-κSe)silver(I)] di­chloro­methane hexa­solvate, [Ag2Br2(C29H24N2Se)4]·6CH2Cl2 or (NHC*Se)4Ag2Br2·6CH2Cl2, (2), via oxidation of the NHC* fragment to 2-seleno­imidazole. This oxidation was observed again in the reaction of NHC*—Cu—Br with KSeCN, yielding catena-poly[[[(1,3-dibenzyl-4,5-diphenyl-2-seleno­imidazole-κSe)copper(I)]-μ-cyanido-κ2C:N] aceto­nitrile monosolvate], {[Cu(CN)(C29H24N2Se)]·C2H3N}n or NHC*Se—CuCN·CH3CN, (3). Compound (1) represents an organic/inorganic salt with AgI in a linear coordination in each of the two cations and in a trigonal coordination in the anion, accompanied by diethyl ether solvent mol­ecules. The tri-blade boomerang-shaped complex anion [Ag(SCN)3]2− present in (1) is characterized by X-ray diffraction for the first time. Compound (2) comprises an isolated centrosymmetric mol­ecule with AgI in a distorted tetra­hedral BrSe3 coordination, together with di­chloro­methane solvent mol­ecules. Compound (3) exhibits a linear polymeric 1[Cu—C≡N—Cu—] chain structure with a seleno­imidazole moiety additionally coordinating to each CuI atom, and completed by aceto­nitrile solvent mol­ecules. Electron densities associated with an additional ether solvent mol­ecule in (1) and two additional di­chloro­methane solvent mol­ecules in (2) were removed with the SQUEEZE procedure [Spek (2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]). Acta Cryst. C71, 9–18] in PLATON.

1. Chemical context

Copper and silver and their compounds exhibit fungicidal properties. For example, a copper di­hydroxide suspension in water – The Bordeaux Mixture – is a well-known early fungicide used in vineyards, while metallic silver has been used as an anti­microbial agent to purify drinking water for a long time. Alexander the Great stored drinking water in silver vessels during his military campaigns (White, 2002[White, R. J. (2002). Br. J. Nurs. 15, 3-8.]). Later, silver nitrate was used to treat wounds and infectious diseases even before the discovery of bacteria (Klasen, 2000[Klasen, H. J. (2000). Burns, 26, 117-130.]). Silver sulfadiazine, discovered in the 1960s, was found to be more effective and safer than silver nitrate in treating burn wounds and is currently the most widely used remedy in burn centres (Fox, 1968[Fox, C. L. (1968). Arch. Surg. 96, 184-188.]). Silver is considered nontoxic to mammalian cells within the determined exposure limits of 0.01–0.1 mg m−3 (Drake & Hazelwood, 2005[Drake, P. L. & Hazelwood, K. J. (2005). Ann. Occup. Hyg. 49, 575-585.]). Nevertheless, silver compounds may cause skin discoloration, known as Argyria (Kim et al., 2009[Kim, Y., Suh, H. S., Cha, H. J., Kim, S. H., Jeong, K. S. & Kim, D. H. (2009). Am. J. Ind. Med. 52, 246-250.]). The active species, the AgI cation, inhibits the respiratory path of sensitive strain organisms, destroys the cell wall, impairs essential enzymes, obstructs metabolic activity and/or causes RNA and DNA alteration (Silver, 2003[Silver, S. (2003). FEMS Microbiol. Rev. 27, 341-353.]; Starodub & Trevors, 1989[Starodub, M. E. & Trevors, J. T. (1989). J. Med. Microbiol. 29, 101-110.]). This topic saw renewed inter­est when Youngs and co-workers published the clean synthesis of N-heterocyclic (NHC) silver acetate derivatives from easily accessible imidazolium halides (Liang et al., 2018[Liang, X., Luan, S., Yin, Z., He, M., He, C., Yin, L., Zou, Y., Yuan, Z., Li, L., Song, X., Lv, C. & Zhang, W. (2018). Eur. J. Med. Chem. 157, 62-80.]); NHC–silver acetates exhibit good chemical stability through covalently bonded silver, which results in significant anti­biotic activity. Particularly well suited are complexes with benzyl-substituted ligands like 1,3-dibenzyl-4,5-di­phenyl­imidazol-2-yl­idene (NHC*; Fig. 1[link]), e.g. NHC*–Ag–OAc (SBC3) (Patil et al., 2011[Patil, S., Deally, A., Gleeson, B., Müller-Bunz, H., Paradisi, F. & Tacke, M. (2011). Metallomics, 3, 74-88.]; Streciwilk et al., 2014[Streciwilk, W., Cassidy, J., Hackenberg, F., Müller-Bunz, H., Paradisi, F. & Tacke, M. (2014). J. Organomet. Chem. 749, 88-99.]; Hackenberg & Tacke, 2014[Hackenberg, F. & Tacke, M. (2014). Dalton Trans. 43, 8144-8153.]), which combine synthesis from a commercially available precursor (4,5-di­phenyl­imidazole) with high anti­microbial activity in vitro (Sharkey et al., 2012[Sharkey, M. A., O'Gara, J. P., Gordon, S. V., Hackenberg, F., Healy, C., Paradisi, F., Patil, S., Schaible, B. & Tacke, M. (2012). Antibiotics, 1, 25-28.]) and in vivo (Browne et al. 2014[Browne, N., Hackenberg, F., Streciwilk, W., Tacke, M. & Kavanagh, K. (2014). Biometals, 27, 745-752.]). In the homologue gold series, the introduction of pseudohalide anions led to stable and bioactive compounds (Dada et al., 2017[Dada, O., Curran, D., O'Beirne, C., Müller-Bunz, H., Zhu, X. & Tacke, M. (2017). J. Organomet. Chem. 840, 30-37.]). In this context, the attempted syntheses of the analogous NHC*—AgI and —CuI thio- and seleno­cyanates as potential anti­microbial species led to unexpected results with the formation of bis­[bis­(1,3-dibenzyl-4,5-di­phenyl­imidazol-2-yl­idene)silver(I)] tris­(thio­cyanato)­argentate(I) diethyl ether disolvate, (1), bis­(μ-1,3-dibenzyl-4,5-diphenyl-2-seleno­imid­azole-κ2Se:Se)bis­[bromido­(1,3-dibenzyl-4,5-diphenyl-2-seleno­imidazole-κSe)silver(I)] di­chloro­methane hexa­solvate, (2), and catena-poly[[[(1,3-dibenzyl-4,5-diphenyl-2-seleno­imidazole-κSe)copper(I)]-μ-cyanido-κ2C:N] aceto­nitrile monosolvate], {[Cu(CN)(C29H24N2Se)]·C2H3N}n or NHC*Se—CuCN·CH3CN, (3), the crystal structures of which are reported in this communication.

[Scheme 1]
[Scheme 2]
[Figure 1]
Figure 1
Lewis structures of the ligands NHC* and NHC*Se.

2. Structural commentary

2.1. [NHC*2Ag]2[Ag(SCN)3]·2Et2O, (1)

Both of the crystallographically distinct [NHC*2Ag]+ cations (Ag1 and Ag2) in the organic/inorganic salt show a nearly linear C—Ag—C angle and two almost identical Ag—C bond lengths (Table 1[link]). In between these two bulky cations is located one [Ag(SCN)3]2− anion with a rare coordination number of three for monovalent silver(I) (Ag3). The corresponding Ag—S bond lengths cover the range 2.4657 (5)–2.5377 (6) Å. The flexibility of the [Ag(SCN)3]2− anion also shows itself in the bond angles, with Ag—S—C angles ranging from 93.45 (8) to 105.56 (9)°, and S—Ag—S angles ranging from 104.96 (2) to 127.68 (2)° (Table 1[link]). As expected, all three SCN ligands are virtually linear. The sum of the S—Ag—S bond angles (Table 1[link]) indicates that the anion is almost planar [the deviation of the Ag3 from the least-squares plane of the three S atoms is 0.1270 (5) Å]. The [Ag(SCN)3]2− anion is situated between the two crystallographically independent cations, but not in the middle (Fig. 2[link]): cation 1 (Ag1) has a shortest distance of 4.161 (2) Å from N3 to Ag3 (line 2 in Fig. 2[link]), whereas cation 2 (Ag2) has a shortest distance of 3.069 (2) Å from C66 to Ag3 (line 1 in Fig. 2[link]). As a consequence of this close association, the benzyl groups in cation 2 are all aligned away from the anion. Due to its greater distance from the anion, the benzyl groups of cation 1 have greater flexibility, allowing it to take a shape suitable to fill gaps in the packing caused by the constraint on cation 2 (Fig. 3[link]). The remaining gaps are filled by two noncoordinating diethyl ether mol­ecules, one of which is highly disordered and could not be refined in terms of atomic sites. The SQUEEZE option (Spek, 2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]) in PLATON was used to compensate for the ill-defined electron density.

[Scheme 3]

Table 1
Selected inter­nuclear distances and bond angles (Å, °) for (1), (2) and (3)

Atoms Distance Atoms Angle
(1)      
Ag1—C8 2.091 (2) S1—Ag3—S2 127.68 (2)
Ag1—C37 2.085 (2) S2—Ag3—S3 103.96 (2)
Ag2—C66 2.097 (2) S3—Ag3—S1 126.94 (2)
Ag2—C95 2.102 (2) Sum 358.58
Ag3—S1 2.4657 (5) C8—Ag1—C37 173.06 (8)
Ag3—S2 2.5377 (6) C66—Ag2—C95 172.01 (7)
Ag3—S3 2.4940 (6) Ag3—S —C117 100.90 (7)
    Ag3—S2—C118 93.45 (8)
Ag3⋯N3 4.161 (2) Ag3—S3—C119 105.56 (9)
Ag3⋯C66 3.069 (2) S1—C117—N9 177.8 (2)
    S2—C118—N10 179.4 (3)
    S3—C119—N11 177.1 (2)
       
(2)      
Ag—Se1 2.6899 (4) Br—Ag—Se1 102.274 (13)
Ag—Se2 2.7677 (4) Br—Ag—Se2 109.628 (12)
Ag—Se2#1 2.7187 (4) Br—Ag—Se2#1 126.883 (14)
Ag—Br 2.6631 (4) Se1—Ag—Se2 110.623 (12)
    Se1—Ag—Se2#1 100.026 (11)
    Se2—Ag—Se2#1 106.352 (11)
    Ag—Se1—C8 94.72 (8)
    Ag—Se2—C37 100.72 (8)
    Ag#1—Se2—C37 108.43 (8)
    Ag—Se2—Ag#1 73.649 (11)
       
(3)      
Cu1—Se1 2.3900 (6) Se1—Cu1—C59 125.06 (12)
Cu1—C59 1.898 (4) Se1—Cu1—N6#2 110.25 (9)
Cu1—N6#2 1.939 (3) C59—Cu1—N6#2 124.68 (14)
    Sum 359.99
Cu2—Se2 2.3861 (6) Se2—Cu2—C60 126.88 (11)
Cu2—C60 1.895 (4) Se2—Cu2—N5 110.28 (10)
Cu2—N5 1.937 (3) C60—Cu2—N5 122.84 (15)
    Sum 360.00
    Cu1—Se1—C8 95.96 (10)
    Cu2—Se2—C37 93.84 (11)
Symmetry codes: (#1) −x + 1, −y + 1, −z + 2; (#2) −x + 2, y + [{1\over 2}], −z + [{3\over 2}].
[Figure 2]
Figure 2
The [Ag(SCN)3]2− anion in (1) with the two closest [Ag(NHC*)2]+ cations. Substituents on the imidazole moiety have been omitted for clarity and displacement ellipsoids are drawn at the 50% probability level.
[Figure 3]
Figure 3
The [Ag(SCN)3]2− anion in (1) with the two closest [Ag(NHC*)2]+ cations. Displacement ellipsoids are drawn at the 50% probability level.

2.2. (NHC*Se)4Ag2Br2·6CH2Cl2, (2)

Compound (2) is characterized by a mol­ecular structure complemented by di­chloro­methane solvent mol­ecules. Two AgI cations and two bridging NHC*Se ligands build up a centrosymmetric four-membered Ag2Se2 ring. Each silver cation carries a further terminal NHC*Se ligand and a terminal bromide ligand, in each case leading to a coordination number of 4 in the shape of a distorted tetra­hedron (Table 1[link] and Fig. 4[link]). One of the bridging Ag—Se distances is 2.7677 (4) Å, significantly longer than the other [2.7187 (4) Å] or the terminal one [2.6899 (4) Å], suggesting that two AgBr(NHC*Se)2 moieties are weakly attached to each other. The Ag—Se—C angles are all strongly bent (Table 1[link]), as one would expect. The bridging and terminal NHC*Se ligand pairs, as well as the two bromide ligands, end up in pseudo-trans positions with respect to each other, allowing an overall compact shape of the uncharged [AgBr(NHC*Se)2]2 complex. Gaps in the packing are filled by di­chloro­methane solvent mol­ecules, two of which were treated with the SQUEEZE option in PLATON.

[Figure 4]
Figure 4
The mol­ecular structure of (2), with phenyl groups represented by their ipso carbon atoms only. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (I) −x + 1, −y + 1, −z + 1.]

2.3. NHC*Se—CuCN·CH3CN, (3)

The structure of (3) is polymeric in nature and contains two distinct CuI atoms. The backbone of the structure is a linear copper–cyanide polymer 1[Cu1—C≡N—Cu2—], where every CuI atom is also coordinated by selenium from a terminal NHC*Se ligand (Fig. 5[link]). The Cu—Se—C angles are in the same region as those in (2) (Table 1[link]). The carbon and nitro­gen atoms of the two cyanide anions can be distinguished, not only by their electron densities, but also by their different bond lengths to CuI atoms, with Cu—N shorter by ≃ 0.04 Å (Table 1[link]). The relatively bulky NHC*Se ligands, which lead to the rare coordination number of 3 of the two CuI cations, move to opposite positions with respect to the copper cyanide polymer, allowing better packing for the overall structure (Fig. 5[link]). The sum of the three angles at Cu1 and Cu2 (Table 1[link]) indicate that the coordination is practically planar at the central copper(I) atoms (the displacement of Cu1 from the least-squares Se1/N6/C5 plane is 0.099 Å and of Cu2 from the least-squares Se2/N5/C60 plane is 0.054 Å). Aceto­nitrile solvent mol­ecules fill voids in the crystal packing.

[Figure 5]
Figure 5
Section of the polymeric structure of (3), with displacement ellipsoids drawn at the 50% probability level. Phenyl groups are represented by their ipso carbons only and aceto­nitrile solvent mol­ecules have been omitted for clarity. [Symmetry codes: (I) −x + 2, y + [{1\over 2}], −z + [{3\over 2}]; (II) −x + 2, y − [{1\over 2}], −z + [{3\over 2}].]

All reactions reported here include cleavage of an Ag– or Cu–carbene bond, suggesting that even at room temperature (Cu) or in refluxing di­chloro­methane (Ag) the targeted NHC*—M—SeCN complexes are not very stable in solution, but are liable to Schlenk-type equilibrium exchange. It is worth mentioning that the syntheses of (2) and (3) require SeCN acting as a selenating agent similar to selenium powder (Verlinden et al., 2015[Verlinden, K., Buhl, H., Frank, W. & Ganter, C. (2015). Eur. J. Inorg. Chem. 2015, 2416-2425.]) or Woollins Reagent (Bockfeld et al., 2017[Bockfeld, D., Bannenberg, T., Jones, P. G. & Tamm, M. (2017). Eur. J. Inorg. Chem. 2017, 3452-3458.]), even under the relatively mild conditions reported here. Thus, neither thio­cyanate nor seleno­cyanate take up their roles as unreactive substituents in these planned substitution reactions. These findings raise questions about the suitability of NHC—MX (M = Cu and Ag; X = pseudohalide) as drugs because drug mol­ecules need to be stable in solution under ambient conditions.

3. Supra­molecular features

In (1), there are some weak nonclassical hydrogen bonds between the cations and the solvent mol­ecules, as detailed in Table 2[link]. One anion has connections to the two cations closest to it, as described above, and one to the cation of an adjacent ion triplet (Fig. 6[link]), linking the ion triplets into a one-dimensional chain. Fig. 7[link] shows a view of (1) along [100] with these contacts shown as dashed lines.

Table 2
Hydrogen-bond geometry (Å, °) for (1)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
C31—H31⋯O1 0.95 2.57 3.361 (4) 141
C32—H32⋯N10i 0.95 2.43 3.327 (4) 157
C40—H40⋯S1ii 0.95 2.82 3.684 (2) 152
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x, y, z-1.
[Figure 6]
Figure 6
The [Ag(SCN)3]2− anion in (1) involved in nonclassical hydrogen-bonding inter­actions, shown as pink dashed lines. Phenyl groups are represented by their ipso carbons only and displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (I) −x + 2, −y + 2, −z + 1; (II) x, y, z + 1.]
[Figure 7]
Figure 7
View of the crystal structure of (1) along [100]. Displacement ellipsoids are drawn at the 50% probability level and hydrogen-bonding inter­actions are shown as pink dashed lines.

All nonclassical hydrogen bonds in (2) and (3) are intra­molecular, and we are not aware of any other noteworthy inter­molecular features in these structures.

4. Database survey

To the best of our knowledge, the crystal structure of (1) is the first report of a salt with the tri-blade boomerang-shaped [Ag(SCN)3]2− ion. The alkaline metals salts Rb2Ag(SCN)3 and Rb2Ag(SCN)3 have one-dimensional polymeric chains as anions rather than isolated [Ag(SCN)3]2− (Thiele & Kehr, 1984[Thiele, G. & Kehr, W. (1984). Z. Anorg. Allg. Chem. 515, 199-206.]). Hathaway et al. (1970[Hathaway, B. J., Billing, D. E., Dudley, R. J., Fereday, R. J. & Tomlinson, A. A. G. (1970). J. Chem. Soc. A, pp. 806-811.]) reported the spectroscopic properties of [Cu(NH3)2Ag(SCN)3] and indicated that they had determined its crystal structure as well. However, in this article, only the space group type (P[\overline{6}]2c) and the number of formula units (Z = 2) were given, not the crystal structure itself. From what is reported it can be gleaned that the anion must be situated on a [\overline{6}] position, i.e. it is planar and adhering to threefold rotation symmetry. If this is true then this is in stark contrast to the [Ag(SCN)3]2− anion reported here, where the Ag—S bond lengths and S—Ag—S and Ag—S—C bond angles cover a wide range. However, since together with the information above only a schematic drawing of the surrounding of the CuII atom was given, we cannot establish structural details of the anion in [Cu(NH3)2Ag(SCN)3] with any degree of certainty.

The Ag—Se distances in (2) fall well within the region reported for similar compounds (Perras et al., 2018[Perras, J. H., Mezibroski, S. M. J., Wiebe, M. & Ritch, J. S. (2018). Dalton Trans. 47, 1471-1478.]; Nahra et al., 2018[Nahra, F., Van Hecke, K., Kennedy, A. R. & Nelson, D. J. (2018). Dalton Trans. 47, 10671-10684.]). Remarkably, at least for the neutral compounds, the distances do not depend on whether the coordination number around the silver is 3 or 4: In N,N-dimesityl­seleno­imidazole–silver nitrate, the Ag—Se bond lengths range from 2.65 to 2.68 Å for the four-coordinate atom and from 2.63 to 2.71 for the three-coordinate atom (Perras et al., 2018[Perras, J. H., Mezibroski, S. M. J., Wiebe, M. & Ritch, J. S. (2018). Dalton Trans. 47, 1471-1478.]).

A comparison with the compounds reported by Kimani et al. (2011[Kimani, M. M., Bayse, C. A. & Brumaghim, J. L. (2011). Dalton Trans. 40, 3711-3723.]) shows a remarkable impact of the cyanide anion on the Cu—Se bond length compared with the corresponding halides. For threefold-coordinated Cu, the distances between Cu and nonbridging Se range from 2.33 to 2.35 Å, whereas both of them in (3) are about 2.39 Å (Table 1[link]). This is closer to the Cu—μ-Se distances (2.41–2.42 Å) reported by Kimani et al. (2011[Kimani, M. M., Bayse, C. A. & Brumaghim, J. L. (2011). Dalton Trans. 40, 3711-3723.]). In other words, cyanide is the better ligand for CuI when compared with halides, and as a result relatively long Cu—Se distances are observed for cyanide derivative (3).

5. Synthesis and crystallization

5.1. [NHC*2Ag]2[Ag(SCN)3]·2Et2O, (1)

1,3-Dibenzyl-4,5-di­phenyl­imidazolium bromide (481 mg, 1.00 mmol), silver oxide (116 mg, 0.500 mmol) and potassium thio­cyanate (107 mg, 1.10 mmol) were suspended in di­chloro­methane (35 ml). After stirring for 20 h under reflux, the solution was filtered and the volume of the solvent was reduced to approximately 5 ml. Pentane (40 ml) was then added and a colourless solid precipitated. The product was filtered off, washed with pentane and dried in vacuo (yield: 366 mg, 0.647 mmol, 65%) as a colourless powder. 1H NMR (300 MHz, CDCl3): δ 1.60 (s, 2H, H2O), 5.49 (s, 4H, Caliph—H), 6.90–7.43 (m, 20H, Car—H). IR (ATR, cm−1): 3028 [ν(CHar)], 2924 [ν(CHaliph)], 2053 [ν(S—C≡N)], 1445, 1348, 1021, 764, 731, 696. Elemental analysis calculated (%): C 63.61, H 4.27, N 7.42; found: C 64.52, H 4.69, N 6.64.

Diethyl ether was diffused into a saturated solution of the crude product in THF; from this solution, that was kept for 10 d at 277 K, the title compound [NHC*2Ag]2[Ag(SCN)3] crystallized in the form of needles of the diethyl ether disolvate.

5.2. (NHC*Se)4Ag2Br2·6CH2Cl2, (2)

1,3-Dibenzyl-4,5-di­phenyl­imidazolium bromide (481 mg, 1.00 mmol), silver oxide (116 mg, 0.500 mmol) and potassium seleno­cyanate (159 mg, 1.10 mmol) were suspended in 35 ml of di­chloro­methane. After stirring for 20 h under reflux, the solution was filtered and the volume of the solvent was reduced to approximately 5 ml. Then 40 ml of pentane were added and a yellow solid precipitated. The product was filtered off, washed with pentane and dried in vacuo (yield: 365 mg, 0.159 mmol, 64%) as a yellow powder. 1H NMR (300 MHz, CDCl3): δ 5.23–5.57 (m, 16H, Caliph—H), 6.77–7.43 (m, 80H, Car—H). IR (ATR, cm−1): 3029 [ν(CHar)], 2926 [ν(CHaliph)], 1447, 1402, 764, 732, 696, 520. Elemental analysis calculated (%): C 59.08, H 4.15, N 4.71; found: C 58.39, H 3.86, N 5.08.

A saturated solution of the compound in di­chloro­methane was prepared at 313 K; from this solution, that was kept for 7 d at 253 K, the title compound (NHC*Se)4Ag2Br2 crystallized as clear pale-yellow block-like prisms of the di­chloro­methane hexa­solvate.

5.3. NHC*Se—CuCN·CH3CN, (3)

(1,3-Dibenzyl-4,5-di­phenyl­imidazol-2-yl­idene)copper(I) bro­mide (270 mg, 0.50 mmol) and potassium seleno­cyanate (72 mg, 0.50 mmol) were suspended in 15 ml of di­chloro­methane followed by 5 ml of water. After stirring for 16 h at room temperature (ca 295K) under nitro­gen, the solutions were filtered and the two phases separated. The aqueous phase was washed with di­chloro­methane (2 × 10 ml) and the organic phase was washed with deionized water (2 × 10 ml). The organic phases were combined and dried over magnesium sulfate. The volume of the solvent was reduced to approximately 5 ml before 20 ml of pentane were added and a colourless solid precipitated. The product was filtered off, washed with pentane and dried in vacuo (yield: 121 mg, 0.212 mmol, 42%) as a colourless powder. 1H NMR (300MHz, CDCl3): δ 7.29–6.97 (m, 20H, CHarom), 5.50 (s, 4H, CH2benz­yl). IR (ATR, cm−1): 3048 (w), 2105 (s) (νCN), 1445 (m, v), 695 (s). M.p. 368 K. Elemental analysis calculated (%) for C30H25N3CuSe: C 63.21, H 4.97, N 7.37; found: C 61.68, H 4.06, N 7.11.

Pentane was diffused into a saturated solution of the crude product in di­chloro­methane/aceto­nitrile 1:1 (v:v). From this solution, kept for 10 d at 277 K, the title compound [(NHC*Se)CuCN] crystallized as needles of the aceto­nitrile solvate.

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. H atoms were placed at calculated positions and treated as riders, with Uiso values set at 1.2Ueq or 1.5Ueq of their respective bonding partners.

Table 3
Experimental details

  (1) (2) (3)
Crystal data
Chemical formula [Ag(C29H24N2)2][Ag(NCS)3]·2C4H10O [Ag2Br2(C29H24N2Se)4]·6CH2Cl2 [Cu(CN)(C29H24N2Se)]·C2H3N
Mr 2248.09 2802.96 610.07
Crystal system, space group Triclinic, P[\overline{1}] Triclinic, P[\overline{1}] Monoclinic, P21/c
Temperature (K) 100 150 100
a, b, c (Å) 14.86462 (8), 19.3714 (1), 19.85451 (9) 13.6265 (1), 14.7422 (1), 16.9397 (2) 13.7704 (3), 14.3398 (3), 28.4102 (7)
α, β, γ (°) 102.7710 (4), 100.8268 (4), 99.5778 (4) 106.4172 (7), 112.2820 (8), 96.2211 (6) 90, 93.024 (2), 90
V3) 5345.84 (5) 2930.04 (5) 5602.2 (2)
Z 2 1 8
Radiation type Cu Kα Mo Kα Mo Kα
μ (mm−1) 5.37 2.58 2.11
Crystal size (mm) 0.32 × 0.06 × 0.04 0.37 × 0.26 × 0.20 0.35 × 0.12 × 0.11
 
Data collection
Diffractometer Rigaku SuperNova, Dual, Cu at zero, Atlas Rigaku SuperNova, Dual, Cu at zero, Atlas Rigaku SuperNova, Dual, Cu at zero, Atlas
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.]) Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.]) Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.])
Tmin, Tmax 0.437, 0.848 0.517, 0.664 0.643, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections 140384, 22376, 19576 119415, 12002, 10726 71725, 11392, 10122
Rint 0.045 0.037 0.038
(sin θ/λ)max−1) 0.632 0.626 0.626
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.080, 1.03 0.035, 0.096, 1.03 0.048, 0.119, 1.06
No. of reflections 22376 12002 11392
No. of parameters 1309 654 687
H-atom treatment H-atom parameters constrained H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.98, −1.13 1.05, −1.49 2.04, −0.56
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

In the crystal structure of (1), one of the phenyl groups was refined as partially disordered over two positions rotated against each other around the ipsopara axis [occupancy ratio 0.55 (2):0.45 (2)]. In the crystal structure of (2), one of the dichoro­methane solvent mol­ecules was refined over two positions [ratio 0.898 (4):0.102 (4)] due to positional disorder around one C—Cl bond.

The SQUEEZE procedure (Spek, 2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]) in PLATON was used to treat regions of disordered solvent mol­ecules in (1) and (2) which could not be modelled in terms of atomic sites. In (1), the number of electrons found in these regions in the unit cell, 82, was assigned to two diethyl ether solvent mol­ecules (ideal 84 electrons). In (2), 84 electrons were found and assigned to two solvent mol­ecules of di­chloro­methane in the unit cell (ideal 84 electrons). Since Z = 2 for (1) and Z = 1 for (2), one solvent mol­ecule of diethyl ether in (1) and two solvent mol­ecules of di­chloro­methane in (2) are missing in the final models and the given chemical formulae and other crystal data given in Table 3[link] take into account these solvent mol­ecules.

Supporting information


Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[bis(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)silver(I)] tris(thiocyanato)argentate(I) diethyl ether disolvate (1) top
Crystal data top
[Ag(C29H24N2)2][Ag(NCS)3]·2C4H10OZ = 2
Mr = 2248.09F(000) = 2320
Triclinic, P1Dx = 1.397 Mg m3
a = 14.86462 (8) ÅCu Kα radiation, λ = 1.54184 Å
b = 19.3714 (1) ÅCell parameters from 59132 reflections
c = 19.85451 (9) Åθ = 3.7–76.7°
α = 102.7710 (4)°µ = 5.37 mm1
β = 100.8268 (4)°T = 100 K
γ = 99.5778 (4)°Needle, colourless
V = 5345.84 (5) Å30.32 × 0.06 × 0.04 mm
Data collection top
Rigaku SuperNova, Dual, Cu at zero, Atlas
diffractometer
22376 independent reflections
Radiation source: micro-focus sealed X-ray tube19576 reflections with I > 2σ(I)
Detector resolution: 10.3196 pixels mm-1Rint = 0.045
ω scansθmax = 76.9°, θmin = 3.4°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 1817
Tmin = 0.437, Tmax = 0.848k = 2424
140384 measured reflectionsl = 2425
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: other
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0438P)2 + 3.189P]
where P = (Fo2 + 2Fc2)/3
22376 reflections(Δ/σ)max = 0.003
1309 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = 1.13 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.

Refinement. The structure was first solved by the Patterson method as implemented in SHELXS. The three silver atoms and one sulfur atom were located. The result was subjected to the Tangens Expansion formula as implemented in SHELXS. Almost all non-hydrogen atoms were located. The remainder was found in the difference fourier map from SHELXL refinements. The PLATON SQUEEZE procedure (A. L. Spek. Acta Cryst. C71, 2015, 9-18) was used to treat regions of disordered solvent which could not be modelled in terms of atomic sites. The number of electrons found in these regions, 82, was assigned to 2 molecules of diethylether. 2 diethylethers would give 84 electrons.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.98105 (2)0.78382 (2)0.03379 (2)0.02968 (4)
C11.21022 (18)0.70910 (14)0.00838 (13)0.0331 (5)
H11.23390.75170.02970.040*
C21.2083 (2)0.64179 (15)0.00485 (16)0.0424 (6)
H21.22960.63830.05190.051*
C31.1753 (2)0.57962 (15)0.05035 (18)0.0507 (7)
H31.17550.53340.04150.061*
C41.1422 (2)0.58496 (15)0.11839 (18)0.0519 (7)
H41.11800.54230.15620.062*
C51.14406 (19)0.65222 (14)0.13158 (13)0.0364 (5)
H51.12210.65550.17870.044*
C61.17778 (15)0.71508 (12)0.07678 (11)0.0252 (4)
C71.17739 (17)0.78740 (12)0.09409 (11)0.0266 (4)
H7A1.22990.79940.11660.032*
H7B1.11810.78390.12840.032*
N11.18670 (13)0.84520 (10)0.03008 (9)0.0227 (3)
C81.11579 (15)0.85001 (12)0.00299 (11)0.0249 (4)
C91.27183 (15)0.88709 (11)0.01320 (11)0.0222 (4)
C101.36079 (17)0.89170 (12)0.01006 (13)0.0295 (5)
C111.3764 (2)0.92388 (17)0.06298 (14)0.0426 (6)
H111.32960.94500.08500.051*
C121.4622 (2)0.9258 (2)0.08513 (16)0.0554 (9)
H121.47150.94610.12340.066*
C131.5306 (3)0.8988 (2)0.0515 (2)0.0630 (9)
H131.58800.90030.06620.076*
C141.5177 (3)0.8688 (2)0.0043 (3)0.0773 (13)
H141.56690.85130.02850.093*
C151.4337 (2)0.8643 (2)0.0246 (2)0.0573 (9)
H151.42460.84270.06200.069*
C161.25234 (14)0.92016 (11)0.07505 (11)0.0226 (4)
C171.31529 (15)0.96909 (12)0.14136 (11)0.0256 (4)
C181.31124 (18)1.04121 (14)0.16332 (13)0.0344 (5)
H181.26791.06040.13510.041*
C191.3699 (2)1.08602 (16)0.22635 (14)0.0423 (6)
H191.36661.13550.24060.051*
C201.4316 (2)1.05965 (17)0.26750 (14)0.0467 (7)
H201.47261.09080.30980.056*
C211.4348 (3)0.9874 (2)0.24781 (18)0.0632 (10)
H211.47640.96840.27760.076*
C221.3773 (2)0.94223 (17)0.18435 (17)0.0533 (8)
H221.38080.89270.17060.064*
N21.15577 (13)0.89728 (10)0.06686 (9)0.0247 (4)
C231.10662 (16)0.91377 (14)0.12398 (12)0.0326 (5)
H23A1.03820.89580.10460.039*
H23B1.11890.96690.14370.039*
C241.13906 (18)0.87875 (14)0.18219 (13)0.0343 (5)
C251.1708 (2)0.92001 (16)0.25172 (14)0.0421 (6)
H251.17030.97020.26300.051*
C261.2033 (3)0.88852 (19)0.30501 (15)0.0544 (8)
H261.22440.91710.35280.065*
C271.2051 (3)0.8163 (2)0.28929 (18)0.0653 (10)
H271.22870.79510.32590.078*
C281.1725 (3)0.77426 (18)0.21979 (18)0.0627 (10)
H281.17350.72410.20870.075*
C291.1384 (2)0.80514 (15)0.16650 (15)0.0467 (7)
H291.11460.77600.11910.056*
C300.7594 (2)0.86196 (16)0.02635 (14)0.0430 (6)
H300.71510.82030.02600.052*
C310.7872 (3)0.9201 (2)0.08573 (18)0.0684 (11)
H310.76140.91810.12570.082*
C320.8500 (4)0.9794 (2)0.0880 (2)0.0846 (17)
H320.86781.01930.12900.102*
C330.8881 (3)0.98228 (17)0.0312 (3)0.0818 (16)
H330.93291.02420.03310.098*
C340.8622 (2)0.92402 (15)0.03031 (18)0.0521 (8)
H340.88980.92590.06950.063*
C350.79556 (17)0.86395 (12)0.03230 (12)0.0312 (5)
C360.76054 (18)0.80201 (12)0.09808 (11)0.0297 (5)
H36A0.69470.80140.11990.036*
H36B0.79860.80930.13280.036*
N30.76572 (13)0.73222 (10)0.08206 (9)0.0238 (4)
C370.84843 (15)0.71588 (12)0.05818 (11)0.0252 (4)
C380.68993 (15)0.67697 (11)0.08559 (10)0.0220 (4)
C390.59068 (15)0.67846 (11)0.11029 (11)0.0233 (4)
C400.55652 (17)0.68480 (13)0.17863 (11)0.0288 (5)
H400.59770.68850.20950.035*
C410.46292 (18)0.68568 (15)0.20165 (13)0.0358 (5)
H410.44040.69010.24820.043*
C420.40217 (18)0.68017 (16)0.15754 (15)0.0404 (6)
H420.33820.68130.17340.049*
C430.4349 (2)0.67302 (18)0.08997 (15)0.0450 (7)
H430.39310.66870.05960.054*
C440.52835 (18)0.67213 (15)0.06656 (13)0.0344 (5)
H440.55020.66720.02010.041*
C450.72822 (15)0.62438 (12)0.06349 (11)0.0231 (4)
C460.68002 (15)0.55211 (12)0.06161 (11)0.0250 (4)
C47A0.6756 (10)0.4947 (3)0.1191 (3)0.0382 (19)0.55 (2)
H47A0.70540.50190.15610.046*0.55 (2)
C48A0.6263 (11)0.4262 (4)0.1213 (4)0.047 (2)0.55 (2)
H48A0.62230.38580.15980.057*0.55 (2)
C47B0.6300 (10)0.4998 (4)0.1238 (4)0.030 (2)0.45 (2)
H47B0.63060.51010.16830.036*0.45 (2)
C48B0.5799 (10)0.4335 (4)0.1225 (4)0.035 (2)0.45 (2)
H48B0.54490.39990.16570.042*0.45 (2)
C490.5803 (2)0.41677 (14)0.06271 (16)0.0413 (6)
H49A0.54960.36950.06330.050*0.45 (2)
H490.54450.37100.06370.050*0.55 (2)
C50A0.5907 (9)0.4743 (5)0.0091 (7)0.046 (2)0.55 (2)
H50A0.56380.46900.02970.056*0.55 (2)
C51A0.6397 (9)0.5417 (5)0.0082 (6)0.0385 (19)0.55 (2)
H51A0.64510.58170.03100.046*0.55 (2)
C50B0.6251 (10)0.4670 (7)0.0033 (6)0.039 (2)0.45 (2)
H50B0.62140.45480.04670.046*0.45 (2)
C51B0.6748 (9)0.5350 (6)0.0034 (5)0.032 (2)0.45 (2)
H51B0.70520.56960.04720.038*0.45 (2)
N40.82539 (13)0.64955 (10)0.04759 (9)0.0253 (4)
C520.89538 (16)0.60961 (13)0.02429 (12)0.0309 (5)
H52A0.95190.62410.04180.037*
H52B0.86990.55720.04640.037*
C530.92407 (16)0.62147 (12)0.05521 (12)0.0275 (4)
C540.9906 (2)0.58529 (14)0.08136 (15)0.0407 (6)
H541.01790.55610.04930.049*
C551.0175 (2)0.59117 (17)0.15341 (17)0.0513 (8)
H551.06250.56580.17060.062*
C560.9789 (2)0.6341 (2)0.20018 (17)0.0566 (9)
H560.99650.63760.24960.068*
C570.9145 (2)0.6719 (2)0.17531 (16)0.0555 (8)
H570.88920.70250.20770.067*
C580.88663 (18)0.66519 (17)0.10261 (13)0.0387 (6)
H580.84180.69070.08560.046*
Ag20.75371 (2)0.69309 (2)0.54662 (2)0.01911 (4)
C590.76475 (15)0.50709 (11)0.46307 (11)0.0225 (4)
H590.82470.53040.45980.027*
C600.69686 (16)0.46941 (12)0.40157 (11)0.0260 (4)
H600.71080.46700.35640.031*
C610.60914 (16)0.43546 (12)0.40584 (12)0.0263 (4)
H610.56330.40950.36380.032*
C620.58851 (16)0.43949 (12)0.47170 (12)0.0274 (4)
H620.52820.41660.47470.033*
C630.65595 (15)0.47693 (12)0.53319 (11)0.0249 (4)
H630.64160.47960.57820.030*
C640.74483 (14)0.51063 (10)0.52924 (11)0.0198 (4)
C650.81645 (14)0.54679 (11)0.59853 (10)0.0199 (4)
H65A0.78390.56960.63370.024*
H65B0.84300.50900.61650.024*
N50.89381 (11)0.60198 (9)0.59393 (8)0.0176 (3)
C660.88138 (14)0.66826 (11)0.58793 (10)0.0183 (4)
C670.98878 (14)0.60157 (11)0.61353 (10)0.0180 (4)
C681.02285 (14)0.53624 (11)0.62232 (10)0.0190 (4)
C690.98347 (14)0.46886 (11)0.57308 (11)0.0218 (4)
H690.93430.46520.53340.026*
C701.01597 (16)0.40742 (11)0.58206 (12)0.0255 (4)
H700.98840.36190.54880.031*
C711.08858 (17)0.41245 (12)0.63940 (13)0.0286 (5)
H711.11090.37050.64530.034*
C721.12857 (17)0.47899 (13)0.68824 (12)0.0288 (5)
H721.17820.48250.72760.035*
C731.09603 (15)0.54048 (12)0.67962 (11)0.0239 (4)
H731.12390.58590.71310.029*
C741.03660 (14)0.66983 (10)0.62029 (10)0.0176 (4)
C751.13793 (14)0.70362 (10)0.64412 (10)0.0190 (4)
C761.20124 (15)0.68387 (11)0.60387 (11)0.0229 (4)
H761.17990.64670.56070.027*
C771.29550 (15)0.71837 (12)0.62661 (12)0.0262 (4)
H771.33830.70490.59880.031*
C781.32722 (15)0.77236 (12)0.68963 (13)0.0278 (4)
H781.39150.79630.70470.033*
C791.26479 (16)0.79140 (12)0.73066 (11)0.0265 (4)
H791.28680.82790.77430.032*
C801.17026 (15)0.75747 (11)0.70843 (11)0.0231 (4)
H801.12780.77070.73670.028*
N60.96896 (11)0.70968 (9)0.60418 (8)0.0174 (3)
C810.98813 (14)0.78589 (10)0.60104 (10)0.0203 (4)
H81A1.04330.81350.63950.024*
H81B0.93370.80700.60930.024*
C821.00677 (15)0.79387 (10)0.53060 (11)0.0208 (4)
C831.09775 (16)0.80758 (12)0.52096 (12)0.0266 (4)
H831.14950.81350.55950.032*
C841.11334 (18)0.81269 (13)0.45497 (14)0.0337 (5)
H841.17560.82190.44870.040*
C851.0382 (2)0.80441 (14)0.39856 (13)0.0379 (6)
H851.04880.80700.35340.045*
C860.9477 (2)0.79239 (15)0.40830 (13)0.0377 (6)
H860.89610.78760.36990.045*
C870.93200 (17)0.78729 (13)0.47376 (12)0.0293 (5)
H870.86960.77920.48000.035*
C880.66481 (17)0.64638 (13)0.33252 (12)0.0301 (5)
H880.69230.68880.37010.036*
C890.6978 (2)0.63552 (17)0.27051 (13)0.0405 (6)
H890.74810.67030.26620.049*
C900.6575 (2)0.57434 (18)0.21551 (14)0.0491 (7)
H900.67970.56720.17320.059*
C910.5850 (3)0.52357 (17)0.22198 (14)0.0540 (8)
H910.55740.48130.18420.065*
C920.5522 (2)0.53423 (14)0.28367 (13)0.0412 (6)
H920.50200.49930.28780.049*
C930.59255 (16)0.59583 (12)0.33951 (11)0.0246 (4)
C940.55979 (15)0.60271 (11)0.40821 (11)0.0214 (4)
H94A0.49550.57270.39770.026*
H94B0.60120.58300.44080.026*
N70.55944 (12)0.67719 (9)0.44431 (8)0.0182 (3)
C950.63428 (14)0.72101 (11)0.49374 (10)0.0186 (4)
C960.48627 (14)0.71328 (11)0.43243 (10)0.0202 (4)
C970.38961 (14)0.67823 (11)0.39126 (11)0.0230 (4)
C980.36889 (17)0.63429 (14)0.32221 (12)0.0321 (5)
H980.41790.62800.29840.039*
C990.27620 (19)0.59946 (15)0.28787 (14)0.0408 (6)
H990.26250.56860.24120.049*
C1000.20452 (17)0.60977 (14)0.32153 (15)0.0395 (6)
H1000.14170.58560.29810.047*
C1010.22370 (16)0.65493 (13)0.38890 (15)0.0357 (5)
H1010.17400.66320.41140.043*
C1020.31620 (16)0.68858 (12)0.42410 (13)0.0292 (5)
H1020.32930.71890.47100.035*
C1030.51846 (14)0.78202 (11)0.47479 (10)0.0198 (4)
C1040.46956 (14)0.84285 (11)0.48426 (11)0.0230 (4)
C1050.43043 (16)0.85935 (12)0.54279 (12)0.0276 (4)
H1050.43870.83380.57840.033*
C1060.37929 (18)0.91328 (14)0.54867 (14)0.0365 (5)
H1060.35200.92440.58830.044*
C1070.3679 (2)0.95088 (15)0.49722 (17)0.0437 (6)
H1070.33280.98770.50150.052*
C1080.4073 (2)0.93514 (17)0.43954 (18)0.0477 (7)
H1080.39970.96140.40440.057*
C1090.45788 (19)0.88118 (14)0.43285 (14)0.0360 (5)
H1090.48470.87030.39300.043*
N80.60883 (12)0.78514 (9)0.51169 (8)0.0188 (3)
C1100.67195 (14)0.84941 (11)0.56130 (10)0.0212 (4)
H11A0.70900.83470.60050.025*
H11B0.63420.88230.58210.025*
C1110.73840 (14)0.89022 (11)0.52734 (11)0.0214 (4)
C1120.81556 (17)0.94234 (12)0.57147 (12)0.0294 (5)
H1120.82720.94900.62140.035*
C1130.87523 (19)0.98436 (14)0.54315 (15)0.0394 (6)
H1130.92701.02010.57380.047*
C1140.85991 (19)0.97460 (14)0.47042 (16)0.0394 (6)
H1140.90061.00390.45110.047*
C1150.78475 (18)0.92178 (14)0.42575 (13)0.0333 (5)
H1150.77480.91420.37570.040*
C1160.72393 (16)0.87995 (12)0.45408 (12)0.0258 (4)
H1160.67230.84420.42330.031*
Ag30.79941 (2)0.72828 (2)0.71384 (2)0.02795 (4)
S10.64189 (4)0.65134 (3)0.65701 (3)0.02631 (10)
C1170.57874 (15)0.71425 (12)0.64988 (11)0.0240 (4)
N90.53253 (14)0.75603 (11)0.64467 (11)0.0297 (4)
S20.84839 (4)0.86528 (3)0.74115 (3)0.03126 (12)
C1180.96150 (18)0.86638 (12)0.77086 (12)0.0295 (5)
N101.04011 (16)0.86674 (12)0.79091 (13)0.0412 (5)
S30.93489 (4)0.69294 (3)0.78243 (3)0.02904 (11)
C1190.89197 (18)0.61118 (13)0.79230 (12)0.0322 (5)
N110.8653 (2)0.55532 (13)0.80169 (13)0.0496 (6)
C1200.9168 (4)0.8774 (4)0.2474 (3)0.136 (3)
H12A0.88180.84630.27080.204*
H12B0.98330.87580.25910.204*
H12C0.89220.86030.19580.204*
C1210.9060 (3)0.9548 (4)0.2729 (2)0.099 (2)
H12D0.93710.97470.32390.119*
H12E0.93500.98580.24580.119*
O10.81017 (17)0.95296 (14)0.26223 (11)0.0551 (5)
C1220.7881 (4)1.0237 (2)0.2809 (2)0.0799 (14)
H12F0.81571.05520.25360.096*
H12G0.81411.04690.33220.096*
C1230.6848 (4)1.0135 (2)0.2638 (3)0.0803 (14)
H12H0.66000.99200.21270.120*
H12I0.66781.06060.27730.120*
H12J0.65810.98120.29010.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02005 (8)0.03206 (9)0.02983 (8)0.00063 (6)0.00112 (6)0.00219 (6)
C10.0323 (12)0.0319 (12)0.0317 (11)0.0030 (10)0.0026 (9)0.0088 (9)
C20.0401 (15)0.0414 (14)0.0482 (15)0.0082 (12)0.0044 (12)0.0220 (12)
C30.0563 (19)0.0295 (13)0.069 (2)0.0084 (12)0.0133 (15)0.0201 (13)
C40.062 (2)0.0268 (13)0.0566 (17)0.0042 (13)0.0075 (15)0.0003 (12)
C50.0387 (14)0.0317 (12)0.0320 (12)0.0053 (10)0.0048 (10)0.0007 (10)
C60.0200 (10)0.0262 (10)0.0272 (10)0.0038 (8)0.0049 (8)0.0039 (8)
C70.0324 (12)0.0255 (10)0.0180 (9)0.0041 (9)0.0037 (8)0.0015 (8)
N10.0224 (9)0.0235 (8)0.0191 (8)0.0029 (7)0.0026 (7)0.0029 (6)
C80.0208 (10)0.0271 (10)0.0235 (10)0.0031 (8)0.0027 (8)0.0033 (8)
C90.0197 (10)0.0222 (9)0.0224 (9)0.0023 (8)0.0028 (8)0.0047 (7)
C100.0263 (11)0.0249 (10)0.0349 (11)0.0015 (9)0.0135 (9)0.0006 (9)
C110.0337 (14)0.0584 (17)0.0352 (13)0.0010 (12)0.0091 (10)0.0169 (12)
C120.0501 (18)0.068 (2)0.0377 (14)0.0167 (16)0.0157 (13)0.0104 (14)
C130.0454 (18)0.060 (2)0.093 (3)0.0130 (16)0.0425 (19)0.0166 (19)
C140.046 (2)0.085 (3)0.135 (4)0.0338 (19)0.046 (2)0.063 (3)
C150.0392 (16)0.065 (2)0.089 (2)0.0229 (15)0.0283 (16)0.0452 (19)
C160.0175 (10)0.0250 (10)0.0227 (9)0.0016 (8)0.0046 (8)0.0036 (8)
C170.0201 (10)0.0302 (11)0.0216 (9)0.0008 (8)0.0038 (8)0.0022 (8)
C180.0320 (12)0.0346 (12)0.0287 (11)0.0054 (10)0.0024 (9)0.0027 (9)
C190.0379 (14)0.0408 (14)0.0337 (13)0.0011 (11)0.0046 (11)0.0093 (11)
C200.0368 (14)0.0554 (17)0.0295 (12)0.0097 (13)0.0041 (10)0.0020 (11)
C210.055 (2)0.061 (2)0.0525 (18)0.0052 (16)0.0274 (15)0.0109 (15)
C220.0471 (17)0.0408 (15)0.0533 (17)0.0046 (13)0.0198 (14)0.0044 (13)
N20.0189 (9)0.0286 (9)0.0231 (8)0.0021 (7)0.0052 (7)0.0019 (7)
C230.0227 (11)0.0401 (13)0.0298 (11)0.0012 (9)0.0117 (9)0.0021 (9)
C240.0317 (12)0.0361 (13)0.0306 (11)0.0052 (10)0.0163 (10)0.0013 (9)
C250.0488 (16)0.0429 (14)0.0308 (12)0.0014 (12)0.0169 (11)0.0015 (11)
C260.073 (2)0.0573 (19)0.0298 (13)0.0016 (16)0.0200 (14)0.0077 (12)
C270.102 (3)0.060 (2)0.0434 (16)0.007 (2)0.0323 (18)0.0267 (15)
C280.102 (3)0.0379 (16)0.0513 (17)0.0022 (17)0.0335 (19)0.0163 (13)
C290.0625 (19)0.0358 (14)0.0361 (13)0.0103 (13)0.0218 (13)0.0046 (11)
C300.0438 (15)0.0458 (15)0.0346 (13)0.0136 (12)0.0040 (11)0.0024 (11)
C310.082 (3)0.070 (2)0.0405 (16)0.041 (2)0.0061 (16)0.0142 (16)
C320.103 (3)0.0426 (19)0.070 (3)0.036 (2)0.050 (3)0.0195 (18)
C330.077 (3)0.0232 (14)0.105 (3)0.0062 (15)0.058 (3)0.0122 (17)
C340.0423 (16)0.0340 (14)0.0654 (19)0.0093 (12)0.0200 (14)0.0238 (13)
C350.0315 (12)0.0228 (10)0.0330 (11)0.0024 (9)0.0048 (9)0.0076 (9)
C360.0367 (13)0.0270 (11)0.0233 (10)0.0010 (9)0.0017 (9)0.0110 (8)
N30.0248 (9)0.0221 (8)0.0206 (8)0.0003 (7)0.0020 (7)0.0046 (6)
C370.0215 (10)0.0283 (11)0.0212 (9)0.0006 (8)0.0026 (8)0.0024 (8)
C380.0223 (10)0.0224 (10)0.0193 (9)0.0021 (8)0.0032 (7)0.0047 (7)
C390.0236 (10)0.0215 (10)0.0241 (10)0.0051 (8)0.0038 (8)0.0055 (8)
C400.0284 (11)0.0362 (12)0.0222 (10)0.0102 (9)0.0050 (8)0.0067 (9)
C410.0316 (13)0.0481 (15)0.0285 (11)0.0157 (11)0.0014 (9)0.0106 (10)
C420.0241 (12)0.0563 (16)0.0450 (14)0.0175 (11)0.0054 (10)0.0175 (12)
C430.0320 (14)0.071 (2)0.0445 (14)0.0209 (13)0.0181 (11)0.0255 (14)
C440.0318 (13)0.0485 (14)0.0300 (11)0.0148 (11)0.0103 (9)0.0172 (10)
C450.0216 (10)0.0262 (10)0.0205 (9)0.0053 (8)0.0037 (8)0.0050 (8)
C460.0237 (10)0.0252 (10)0.0264 (10)0.0076 (8)0.0023 (8)0.0087 (8)
C47A0.051 (6)0.030 (3)0.032 (3)0.004 (3)0.008 (3)0.0094 (19)
C48A0.069 (7)0.023 (3)0.039 (3)0.003 (3)0.004 (3)0.007 (2)
C47B0.037 (5)0.026 (3)0.025 (3)0.002 (3)0.003 (3)0.008 (2)
C48B0.043 (5)0.023 (3)0.032 (3)0.003 (3)0.001 (3)0.002 (2)
C490.0378 (14)0.0285 (12)0.0535 (16)0.0001 (10)0.0000 (12)0.0165 (11)
C50A0.049 (6)0.037 (3)0.065 (5)0.010 (4)0.028 (5)0.027 (3)
C51A0.043 (5)0.029 (3)0.043 (4)0.006 (3)0.012 (4)0.009 (3)
C50B0.044 (6)0.037 (4)0.035 (4)0.000 (4)0.012 (4)0.013 (3)
C51B0.035 (5)0.037 (4)0.018 (3)0.007 (4)0.003 (3)0.008 (2)
N40.0211 (9)0.0272 (9)0.0237 (8)0.0052 (7)0.0012 (7)0.0023 (7)
C520.0224 (11)0.0345 (12)0.0315 (11)0.0105 (9)0.0001 (9)0.0020 (9)
C530.0207 (10)0.0269 (11)0.0326 (11)0.0009 (8)0.0019 (8)0.0099 (9)
C540.0360 (14)0.0294 (12)0.0478 (15)0.0095 (10)0.0071 (11)0.0045 (11)
C550.0502 (17)0.0448 (16)0.0539 (17)0.0109 (13)0.0110 (14)0.0216 (13)
C560.0475 (17)0.090 (3)0.0409 (15)0.0136 (17)0.0064 (13)0.0389 (16)
C570.0427 (16)0.099 (3)0.0359 (14)0.0271 (17)0.0180 (12)0.0252 (16)
C580.0291 (12)0.0615 (17)0.0331 (12)0.0190 (12)0.0101 (10)0.0188 (12)
Ag20.01516 (7)0.02111 (7)0.02099 (7)0.00652 (5)0.00277 (5)0.00464 (5)
C590.0174 (9)0.0244 (10)0.0258 (10)0.0048 (8)0.0069 (8)0.0048 (8)
C600.0256 (11)0.0266 (10)0.0239 (10)0.0059 (9)0.0068 (8)0.0015 (8)
C610.0241 (11)0.0218 (10)0.0271 (10)0.0019 (8)0.0019 (8)0.0000 (8)
C620.0207 (10)0.0269 (11)0.0313 (11)0.0019 (8)0.0057 (8)0.0060 (9)
C630.0214 (10)0.0267 (10)0.0257 (10)0.0010 (8)0.0074 (8)0.0066 (8)
C640.0171 (9)0.0171 (9)0.0247 (9)0.0046 (7)0.0045 (7)0.0045 (7)
C650.0163 (9)0.0213 (9)0.0226 (9)0.0034 (7)0.0059 (7)0.0063 (7)
N50.0148 (8)0.0178 (8)0.0195 (7)0.0044 (6)0.0031 (6)0.0037 (6)
C660.0170 (9)0.0207 (9)0.0175 (8)0.0058 (7)0.0044 (7)0.0040 (7)
C670.0160 (9)0.0209 (9)0.0172 (8)0.0056 (7)0.0047 (7)0.0029 (7)
C680.0165 (9)0.0198 (9)0.0235 (9)0.0063 (7)0.0077 (7)0.0072 (7)
C690.0182 (9)0.0215 (9)0.0261 (9)0.0042 (8)0.0064 (8)0.0058 (8)
C700.0245 (11)0.0193 (9)0.0341 (11)0.0055 (8)0.0120 (9)0.0048 (8)
C710.0297 (12)0.0250 (10)0.0395 (12)0.0124 (9)0.0147 (9)0.0150 (9)
C720.0275 (11)0.0328 (11)0.0299 (11)0.0122 (9)0.0047 (9)0.0138 (9)
C730.0236 (10)0.0254 (10)0.0230 (9)0.0073 (8)0.0044 (8)0.0064 (8)
C740.0158 (9)0.0202 (9)0.0173 (8)0.0067 (7)0.0044 (7)0.0035 (7)
C750.0163 (9)0.0181 (9)0.0222 (9)0.0041 (7)0.0033 (7)0.0056 (7)
C760.0206 (10)0.0190 (9)0.0282 (10)0.0059 (8)0.0056 (8)0.0035 (8)
C770.0198 (10)0.0243 (10)0.0373 (11)0.0078 (8)0.0109 (9)0.0077 (9)
C780.0171 (10)0.0258 (10)0.0388 (12)0.0025 (8)0.0022 (8)0.0103 (9)
C790.0243 (11)0.0234 (10)0.0258 (10)0.0016 (8)0.0006 (8)0.0021 (8)
C800.0204 (10)0.0254 (10)0.0223 (9)0.0046 (8)0.0055 (8)0.0038 (8)
N60.0156 (8)0.0181 (8)0.0192 (7)0.0057 (6)0.0043 (6)0.0045 (6)
C810.0209 (10)0.0171 (9)0.0227 (9)0.0055 (7)0.0052 (7)0.0034 (7)
C820.0230 (10)0.0157 (9)0.0247 (9)0.0051 (7)0.0066 (8)0.0054 (7)
C830.0250 (11)0.0246 (10)0.0315 (11)0.0055 (8)0.0071 (9)0.0097 (8)
C840.0338 (13)0.0337 (12)0.0413 (13)0.0085 (10)0.0193 (10)0.0160 (10)
C850.0512 (16)0.0351 (13)0.0322 (12)0.0061 (11)0.0168 (11)0.0153 (10)
C860.0406 (14)0.0409 (14)0.0306 (12)0.0025 (11)0.0019 (10)0.0170 (10)
C870.0255 (11)0.0316 (11)0.0327 (11)0.0052 (9)0.0051 (9)0.0146 (9)
C880.0298 (12)0.0352 (12)0.0263 (10)0.0080 (10)0.0099 (9)0.0065 (9)
C890.0397 (14)0.0568 (17)0.0314 (12)0.0135 (12)0.0169 (11)0.0152 (11)
C900.067 (2)0.0628 (19)0.0240 (12)0.0252 (16)0.0191 (12)0.0097 (12)
C910.086 (2)0.0454 (16)0.0249 (12)0.0105 (16)0.0151 (14)0.0025 (11)
C920.0588 (18)0.0314 (13)0.0261 (11)0.0009 (12)0.0077 (11)0.0007 (9)
C930.0260 (11)0.0257 (10)0.0216 (9)0.0085 (8)0.0046 (8)0.0041 (8)
C940.0208 (10)0.0191 (9)0.0238 (9)0.0052 (7)0.0052 (8)0.0042 (7)
N70.0163 (8)0.0189 (8)0.0197 (7)0.0052 (6)0.0034 (6)0.0050 (6)
C950.0173 (9)0.0207 (9)0.0193 (9)0.0059 (7)0.0058 (7)0.0058 (7)
C960.0175 (9)0.0218 (9)0.0230 (9)0.0069 (8)0.0045 (7)0.0079 (7)
C970.0175 (10)0.0204 (9)0.0300 (10)0.0041 (8)0.0005 (8)0.0096 (8)
C980.0248 (11)0.0384 (13)0.0283 (11)0.0035 (10)0.0021 (9)0.0082 (9)
C990.0340 (14)0.0413 (14)0.0355 (13)0.0008 (11)0.0102 (10)0.0085 (11)
C1000.0207 (11)0.0328 (12)0.0566 (16)0.0027 (9)0.0117 (10)0.0182 (11)
C1010.0169 (11)0.0299 (12)0.0615 (16)0.0046 (9)0.0062 (10)0.0171 (11)
C1020.0217 (11)0.0245 (10)0.0410 (12)0.0052 (8)0.0044 (9)0.0096 (9)
C1030.0168 (9)0.0221 (9)0.0206 (9)0.0063 (7)0.0023 (7)0.0061 (7)
C1040.0170 (9)0.0224 (10)0.0283 (10)0.0062 (8)0.0018 (8)0.0051 (8)
C1050.0250 (11)0.0268 (11)0.0278 (10)0.0094 (9)0.0019 (8)0.0017 (8)
C1060.0303 (12)0.0353 (13)0.0402 (13)0.0149 (10)0.0071 (10)0.0024 (10)
C1070.0358 (14)0.0348 (13)0.0654 (18)0.0231 (11)0.0098 (13)0.0130 (12)
C1080.0467 (16)0.0485 (16)0.0673 (19)0.0299 (14)0.0192 (14)0.0349 (15)
C1090.0350 (13)0.0412 (14)0.0444 (13)0.0202 (11)0.0155 (11)0.0228 (11)
N80.0167 (8)0.0202 (8)0.0192 (7)0.0066 (6)0.0024 (6)0.0042 (6)
C1100.0193 (10)0.0212 (9)0.0206 (9)0.0044 (8)0.0027 (7)0.0021 (7)
C1110.0193 (10)0.0192 (9)0.0271 (10)0.0083 (8)0.0054 (8)0.0056 (7)
C1120.0268 (11)0.0262 (11)0.0315 (11)0.0031 (9)0.0046 (9)0.0039 (9)
C1130.0318 (13)0.0320 (12)0.0484 (14)0.0032 (10)0.0084 (11)0.0066 (11)
C1140.0359 (14)0.0339 (13)0.0558 (16)0.0050 (11)0.0217 (12)0.0192 (11)
C1150.0374 (13)0.0367 (12)0.0362 (12)0.0163 (10)0.0175 (10)0.0170 (10)
C1160.0251 (11)0.0260 (10)0.0286 (10)0.0098 (8)0.0073 (8)0.0077 (8)
Ag30.02101 (8)0.03363 (9)0.02613 (8)0.00446 (6)0.00344 (6)0.00431 (6)
S10.0207 (2)0.0273 (2)0.0305 (2)0.00565 (19)0.00707 (19)0.0052 (2)
C1170.0205 (10)0.0260 (10)0.0217 (9)0.0006 (8)0.0063 (8)0.0015 (8)
N90.0246 (9)0.0307 (10)0.0347 (10)0.0072 (8)0.0097 (8)0.0069 (8)
S20.0326 (3)0.0309 (3)0.0323 (3)0.0114 (2)0.0085 (2)0.0083 (2)
C1180.0350 (13)0.0242 (10)0.0266 (10)0.0047 (9)0.0089 (9)0.0006 (8)
N100.0338 (12)0.0299 (11)0.0511 (13)0.0025 (9)0.0049 (10)0.0003 (9)
S30.0251 (3)0.0338 (3)0.0254 (2)0.0032 (2)0.0011 (2)0.0084 (2)
C1190.0343 (13)0.0339 (12)0.0232 (10)0.0057 (10)0.0007 (9)0.0032 (9)
N110.0614 (16)0.0344 (12)0.0413 (12)0.0008 (11)0.0036 (11)0.0076 (10)
C1200.090 (4)0.268 (9)0.169 (6)0.122 (5)0.092 (4)0.182 (6)
C1210.047 (2)0.195 (6)0.073 (3)0.014 (3)0.0118 (19)0.083 (4)
O10.0558 (13)0.0739 (15)0.0417 (11)0.0120 (11)0.0185 (10)0.0230 (10)
C1220.132 (4)0.049 (2)0.057 (2)0.007 (2)0.046 (2)0.0105 (16)
C1230.120 (4)0.056 (2)0.102 (3)0.041 (2)0.077 (3)0.036 (2)
Geometric parameters (Å, º) top
Ag1—C372.085 (2)C60—H600.9500
Ag1—C82.091 (2)C61—C621.387 (3)
C1—C21.383 (4)C61—H610.9500
C1—C61.390 (3)C62—C631.388 (3)
C1—H10.9500C62—H620.9500
C2—C31.382 (4)C63—C641.397 (3)
C2—H20.9500C63—H630.9500
C3—C41.381 (5)C64—C651.514 (3)
C3—H30.9500C65—N51.465 (2)
C4—C51.382 (4)C65—H65A0.9900
C4—H40.9500C65—H65B0.9900
C5—C61.387 (3)N5—C661.355 (3)
C5—H50.9500N5—C671.394 (3)
C6—C71.515 (3)C66—N61.350 (3)
C7—N11.463 (3)C67—C741.358 (3)
C7—H7A0.9900C67—C681.472 (3)
C7—H7B0.9900C68—C731.396 (3)
N1—C81.348 (3)C68—C691.403 (3)
N1—C91.393 (3)C69—C701.391 (3)
C8—N21.350 (3)C69—H690.9500
C9—C161.360 (3)C70—C711.387 (3)
C9—C101.476 (3)C70—H700.9500
C10—C111.371 (4)C71—C721.390 (3)
C10—C151.414 (4)C71—H710.9500
C11—C121.423 (4)C72—C731.390 (3)
C11—H110.9500C72—H720.9500
C12—C131.353 (5)C73—H730.9500
C12—H120.9500C74—N61.398 (2)
C13—C141.389 (6)C74—C751.479 (3)
C13—H130.9500C75—C761.392 (3)
C14—C151.378 (5)C75—C801.401 (3)
C14—H140.9500C76—C771.390 (3)
C15—H150.9500C76—H760.9500
C16—N21.397 (3)C77—C781.385 (3)
C16—C171.482 (3)C77—H770.9500
C17—C221.382 (4)C78—C791.388 (3)
C17—C181.383 (3)C78—H780.9500
C18—C191.392 (3)C79—C801.390 (3)
C18—H180.9500C79—H790.9500
C19—C201.352 (4)C80—H800.9500
C19—H190.9500N6—C811.474 (2)
C20—C211.378 (5)C81—C821.511 (3)
C20—H200.9500C81—H81A0.9900
C21—C221.394 (4)C81—H81B0.9900
C21—H210.9500C82—C831.391 (3)
C22—H220.9500C82—C871.394 (3)
N2—C231.467 (3)C83—C841.394 (3)
C23—C241.508 (4)C83—H830.9500
C23—H23A0.9900C84—C851.385 (4)
C23—H23B0.9900C84—H840.9500
C24—C251.382 (3)C85—C861.385 (4)
C24—C291.389 (4)C85—H850.9500
C25—C261.384 (5)C86—C871.384 (3)
C25—H250.9500C86—H860.9500
C26—C271.371 (5)C87—H870.9500
C26—H260.9500C88—C931.378 (3)
C27—C281.387 (5)C88—C891.396 (3)
C27—H270.9500C88—H880.9500
C28—C291.383 (5)C89—C901.379 (4)
C28—H280.9500C89—H890.9500
C29—H290.9500C90—C911.379 (5)
C30—C351.376 (4)C90—H900.9500
C30—C311.380 (4)C91—C921.387 (4)
C30—H300.9500C91—H910.9500
C31—C321.341 (7)C92—C931.393 (3)
C31—H310.9500C92—H920.9500
C32—C331.360 (8)C93—C941.519 (3)
C32—H320.9500C94—N71.463 (3)
C33—C341.409 (5)C94—H94A0.9900
C33—H330.9500C94—H94B0.9900
C34—C351.385 (4)N7—C951.352 (3)
C34—H340.9500N7—C961.399 (3)
C35—C361.503 (3)C95—N81.351 (3)
C36—N31.466 (3)C96—C1031.361 (3)
C36—H36A0.9900C96—C971.477 (3)
C36—H36B0.9900C97—C981.392 (3)
N3—C371.347 (3)C97—C1021.392 (3)
N3—C381.398 (3)C98—C991.397 (3)
C37—N41.346 (3)C98—H980.9500
C38—C451.361 (3)C99—C1001.379 (4)
C38—C391.472 (3)C99—H990.9500
C39—C441.392 (3)C100—C1011.375 (4)
C39—C401.396 (3)C100—H1000.9500
C40—C411.385 (3)C101—C1021.394 (3)
C40—H400.9500C101—H1010.9500
C41—C421.378 (4)C102—H1020.9500
C41—H410.9500C103—N81.389 (3)
C42—C431.384 (4)C103—C1041.480 (3)
C42—H420.9500C104—C1091.391 (3)
C43—C441.384 (4)C104—C1051.394 (3)
C43—H430.9500C105—C1061.388 (3)
C44—H440.9500C105—H1050.9500
C45—N41.396 (3)C106—C1071.381 (4)
C45—C461.475 (3)C106—H1060.9500
C46—C51A1.348 (9)C107—C1081.380 (4)
C46—C47A1.390 (7)C107—H1070.9500
C46—C47B1.399 (8)C108—C1091.383 (4)
C46—C51B1.415 (9)C108—H1080.9500
C47A—C48A1.392 (9)C109—H1090.9500
C47A—H47A0.9500N8—C1101.457 (3)
C48A—C491.484 (12)C110—C1111.510 (3)
C48A—H48A0.9500C110—H11A0.9900
C47B—C48B1.382 (10)C110—H11B0.9900
C47B—H47B0.9500C111—C1161.394 (3)
C48B—C491.297 (8)C111—C1121.396 (3)
C48B—H48B0.9500C112—C1131.384 (4)
C49—C50A1.325 (11)C112—H1120.9500
C49—C50B1.415 (11)C113—C1141.384 (4)
C49—H49A0.9500C113—H1130.9500
C49—H490.9500C114—C1151.388 (4)
C50A—C51A1.379 (13)C114—H1140.9500
C50A—H50A0.9500C115—C1161.393 (3)
C51A—H51A0.9500C115—H1150.9500
C50B—C51B1.399 (15)C116—H1160.9500
C50B—H50B0.9500Ag3—S12.4657 (5)
C51B—H51B0.9500Ag3—S32.4940 (6)
N4—C521.463 (3)Ag3—S22.5377 (6)
C52—C531.510 (3)S1—C1171.671 (2)
C52—H52A0.9900C117—N91.154 (3)
C52—H52B0.9900S2—C1181.669 (3)
C53—C581.384 (4)C118—N101.160 (3)
C53—C541.392 (3)S3—C1191.674 (3)
C54—C551.385 (4)C119—N111.156 (4)
C54—H540.9500C120—C1211.517 (9)
C55—C561.379 (5)C120—H12A0.9800
C55—H550.9500C120—H12B0.9800
C56—C571.384 (5)C120—H12C0.9800
C56—H560.9500C121—O11.394 (5)
C57—C581.395 (4)C121—H12D0.9900
C57—H570.9500C121—H12E0.9900
C58—H580.9500O1—C1221.447 (5)
Ag2—C662.097 (2)C122—C1231.479 (7)
Ag2—C952.102 (2)C122—H12F0.9900
C59—C641.390 (3)C122—H12G0.9900
C59—C601.393 (3)C123—H12H0.9800
C59—H590.9500C123—H12I0.9800
C60—C611.386 (3)C123—H12J0.9800
C37—Ag1—C8173.06 (8)C60—C61—H61120.1
C2—C1—C6120.6 (2)C62—C61—H61120.1
C2—C1—H1119.7C61—C62—C63120.0 (2)
C6—C1—H1119.7C61—C62—H62120.0
C3—C2—C1120.0 (3)C63—C62—H62120.0
C3—C2—H2120.0C62—C63—C64120.4 (2)
C1—C2—H2120.0C62—C63—H63119.8
C4—C3—C2119.7 (3)C64—C63—H63119.8
C4—C3—H3120.1C59—C64—C63119.32 (19)
C2—C3—H3120.1C59—C64—C65123.21 (18)
C3—C4—C5120.2 (3)C63—C64—C65117.42 (18)
C3—C4—H4119.9N5—C65—C64114.90 (16)
C5—C4—H4119.9N5—C65—H65A108.5
C4—C5—C6120.7 (3)C64—C65—H65A108.5
C4—C5—H5119.7N5—C65—H65B108.5
C6—C5—H5119.7C64—C65—H65B108.5
C5—C6—C1118.7 (2)H65A—C65—H65B107.5
C5—C6—C7118.5 (2)C66—N5—C67111.26 (16)
C1—C6—C7122.8 (2)C66—N5—C65121.43 (16)
N1—C7—C6111.19 (17)C67—N5—C65125.21 (16)
N1—C7—H7A109.4N6—C66—N5104.81 (16)
C6—C7—H7A109.4N6—C66—Ag2128.78 (14)
N1—C7—H7B109.4N5—C66—Ag2125.76 (14)
C6—C7—H7B109.4C74—C67—N5106.39 (17)
H7A—C7—H7B108.0C74—C67—C68130.61 (18)
C8—N1—C9111.66 (17)N5—C67—C68122.99 (17)
C8—N1—C7121.59 (18)C73—C68—C69118.72 (19)
C9—N1—C7124.57 (18)C73—C68—C67120.38 (18)
N1—C8—N2104.69 (18)C69—C68—C67120.90 (18)
N1—C8—Ag1125.14 (15)C70—C69—C68120.41 (19)
N2—C8—Ag1129.44 (16)C70—C69—H69119.8
C16—C9—N1106.11 (18)C68—C69—H69119.8
C16—C9—C10131.06 (19)C71—C70—C69120.2 (2)
N1—C9—C10122.82 (19)C71—C70—H70119.9
C11—C10—C15118.6 (2)C69—C70—H70119.9
C11—C10—C9122.0 (2)C70—C71—C72119.9 (2)
C15—C10—C9119.4 (2)C70—C71—H71120.0
C10—C11—C12120.4 (3)C72—C71—H71120.0
C10—C11—H11119.8C71—C72—C73120.1 (2)
C12—C11—H11119.8C71—C72—H72120.0
C13—C12—C11119.8 (3)C73—C72—H72120.0
C13—C12—H12120.1C72—C73—C68120.7 (2)
C11—C12—H12120.1C72—C73—H73119.7
C12—C13—C14120.6 (3)C68—C73—H73119.7
C12—C13—H13119.7C67—C74—N6106.25 (17)
C14—C13—H13119.7C67—C74—C75131.52 (18)
C15—C14—C13120.1 (4)N6—C74—C75122.10 (17)
C15—C14—H14119.9C76—C75—C80119.53 (19)
C13—C14—H14119.9C76—C75—C74121.65 (18)
C14—C15—C10120.3 (3)C80—C75—C74118.82 (18)
C14—C15—H15119.8C77—C76—C75120.21 (19)
C10—C15—H15119.8C77—C76—H76119.9
C9—C16—N2106.17 (18)C75—C76—H76119.9
C9—C16—C17130.6 (2)C78—C77—C76120.3 (2)
N2—C16—C17123.25 (18)C78—C77—H77119.9
C22—C17—C18118.4 (2)C76—C77—H77119.9
C22—C17—C16120.0 (2)C77—C78—C79119.8 (2)
C18—C17—C16121.6 (2)C77—C78—H78120.1
C17—C18—C19120.7 (3)C79—C78—H78120.1
C17—C18—H18119.6C78—C79—C80120.5 (2)
C19—C18—H18119.6C78—C79—H79119.8
C20—C19—C18120.5 (3)C80—C79—H79119.8
C20—C19—H19119.7C79—C80—C75119.7 (2)
C18—C19—H19119.7C79—C80—H80120.2
C19—C20—C21119.8 (2)C75—C80—H80120.2
C19—C20—H20120.1C66—N6—C74111.27 (16)
C21—C20—H20120.1C66—N6—C81122.92 (17)
C20—C21—C22120.2 (3)C74—N6—C81125.73 (17)
C20—C21—H21119.9N6—C81—C82112.59 (16)
C22—C21—H21119.9N6—C81—H81A109.1
C17—C22—C21120.3 (3)C82—C81—H81A109.1
C17—C22—H22119.8N6—C81—H81B109.1
C21—C22—H22119.8C82—C81—H81B109.1
C8—N2—C16111.32 (18)H81A—C81—H81B107.8
C8—N2—C23123.91 (19)C83—C82—C87118.8 (2)
C16—N2—C23124.17 (18)C83—C82—C81121.23 (19)
N2—C23—C24110.6 (2)C87—C82—C81119.93 (19)
N2—C23—H23A109.5C82—C83—C84120.3 (2)
C24—C23—H23A109.5C82—C83—H83119.8
N2—C23—H23B109.5C84—C83—H83119.8
C24—C23—H23B109.5C85—C84—C83120.1 (2)
H23A—C23—H23B108.1C85—C84—H84119.9
C25—C24—C29119.4 (3)C83—C84—H84119.9
C25—C24—C23120.1 (2)C86—C85—C84119.7 (2)
C29—C24—C23120.5 (2)C86—C85—H85120.1
C24—C25—C26120.3 (3)C84—C85—H85120.1
C24—C25—H25119.9C87—C86—C85120.2 (2)
C26—C25—H25119.9C87—C86—H86119.9
C27—C26—C25120.4 (3)C85—C86—H86119.9
C27—C26—H26119.8C86—C87—C82120.7 (2)
C25—C26—H26119.8C86—C87—H87119.7
C26—C27—C28119.7 (3)C82—C87—H87119.7
C26—C27—H27120.1C93—C88—C89120.3 (2)
C28—C27—H27120.1C93—C88—H88119.8
C29—C28—C27120.1 (3)C89—C88—H88119.8
C29—C28—H28119.9C90—C89—C88120.1 (3)
C27—C28—H28119.9C90—C89—H89120.0
C28—C29—C24120.0 (3)C88—C89—H89120.0
C28—C29—H29120.0C91—C90—C89120.0 (2)
C24—C29—H29120.0C91—C90—H90120.0
C35—C30—C31120.3 (3)C89—C90—H90120.0
C35—C30—H30119.8C90—C91—C92120.0 (3)
C31—C30—H30119.8C90—C91—H91120.0
C32—C31—C30121.2 (4)C92—C91—H91120.0
C32—C31—H31119.4C91—C92—C93120.4 (3)
C30—C31—H31119.4C91—C92—H92119.8
C31—C32—C33119.7 (3)C93—C92—H92119.8
C31—C32—H32120.1C88—C93—C92119.2 (2)
C33—C32—H32120.1C88—C93—C94121.89 (19)
C32—C33—C34121.0 (4)C92—C93—C94118.8 (2)
C32—C33—H33119.5N7—C94—C93113.90 (17)
C34—C33—H33119.5N7—C94—H94A108.8
C35—C34—C33118.4 (4)C93—C94—H94A108.8
C35—C34—H34120.8N7—C94—H94B108.8
C33—C34—H34120.8C93—C94—H94B108.8
C30—C35—C34119.3 (3)H94A—C94—H94B107.7
C30—C35—C36119.7 (2)C95—N7—C96111.11 (16)
C34—C35—C36121.0 (3)C95—N7—C94122.37 (17)
N3—C36—C35111.53 (17)C96—N7—C94126.49 (17)
N3—C36—H36A109.3N8—C95—N7104.77 (17)
C35—C36—H36A109.3N8—C95—Ag2125.79 (14)
N3—C36—H36B109.3N7—C95—Ag2128.50 (14)
C35—C36—H36B109.3C103—C96—N7106.17 (17)
H36A—C36—H36B108.0C103—C96—C97128.07 (19)
C37—N3—C38111.70 (18)N7—C96—C97125.00 (18)
C37—N3—C36121.70 (19)C98—C97—C102118.8 (2)
C38—N3—C36126.54 (19)C98—C97—C96123.2 (2)
N4—C37—N3104.74 (18)C102—C97—C96118.02 (19)
N4—C37—Ag1128.26 (16)C97—C98—C99120.1 (2)
N3—C37—Ag1126.73 (16)C97—C98—H98119.9
C45—C38—N3105.77 (18)C99—C98—H98119.9
C45—C38—C39129.59 (19)C100—C99—C98120.2 (2)
N3—C38—C39124.63 (19)C100—C99—H99119.9
C44—C39—C40118.5 (2)C98—C99—H99119.9
C44—C39—C38120.78 (19)C101—C100—C99120.2 (2)
C40—C39—C38120.7 (2)C101—C100—H100119.9
C41—C40—C39120.4 (2)C99—C100—H100119.9
C41—C40—H40119.8C100—C101—C102119.9 (2)
C39—C40—H40119.8C100—C101—H101120.1
C42—C41—C40120.5 (2)C102—C101—H101120.1
C42—C41—H41119.7C97—C102—C101120.7 (2)
C40—C41—H41119.7C97—C102—H102119.6
C41—C42—C43119.7 (2)C101—C102—H102119.6
C41—C42—H42120.2C96—C103—N8106.35 (17)
C43—C42—H42120.2C96—C103—C104129.11 (19)
C44—C43—C42120.2 (2)N8—C103—C104124.51 (18)
C44—C43—H43119.9C109—C104—C105119.6 (2)
C42—C43—H43119.9C109—C104—C103120.2 (2)
C43—C44—C39120.8 (2)C105—C104—C103120.07 (19)
C43—C44—H44119.6C106—C105—C104119.6 (2)
C39—C44—H44119.6C106—C105—H105120.2
C38—C45—N4106.32 (18)C104—C105—H105120.2
C38—C45—C46128.4 (2)C107—C106—C105120.3 (2)
N4—C45—C46125.13 (19)C107—C106—H106119.9
C51A—C46—C47A121.0 (5)C105—C106—H106119.9
C47B—C46—C51B116.9 (5)C108—C107—C106120.2 (2)
C51A—C46—C45122.4 (4)C108—C107—H107119.9
C47A—C46—C45116.6 (3)C106—C107—H107119.9
C47B—C46—C45121.5 (3)C107—C108—C109120.0 (3)
C51B—C46—C45121.4 (4)C107—C108—H108120.0
C46—C47A—C48A118.4 (6)C109—C108—H108120.0
C46—C47A—H47A120.8C108—C109—C104120.2 (2)
C48A—C47A—H47A120.8C108—C109—H109119.9
C47A—C48A—C49119.4 (6)C104—C109—H109119.9
C47A—C48A—H48A120.3C95—N8—C103111.58 (16)
C49—C48A—H48A120.3C95—N8—C110122.79 (17)
C48B—C47B—C46122.0 (6)C103—N8—C110125.57 (17)
C48B—C47B—H47B119.0N8—C110—C111113.24 (16)
C46—C47B—H47B119.0N8—C110—H11A108.9
C49—C48B—C47B120.5 (6)C111—C110—H11A108.9
C49—C48B—H48B119.8N8—C110—H11B108.9
C47B—C48B—H48B119.8C111—C110—H11B108.9
C48B—C49—C50B121.9 (6)H11A—C110—H11B107.7
C50A—C49—C48A117.9 (5)C116—C111—C112118.8 (2)
C48B—C49—H49A119.0C116—C111—C110122.77 (19)
C50B—C49—H49A119.0C112—C111—C110118.43 (19)
C50A—C49—H49121.1C113—C112—C111120.7 (2)
C48A—C49—H49121.1C113—C112—H112119.7
C49—C50A—C51A121.7 (8)C111—C112—H112119.7
C49—C50A—H50A119.2C114—C113—C112120.4 (2)
C51A—C50A—H50A119.2C114—C113—H113119.8
C46—C51A—C50A121.6 (8)C112—C113—H113119.8
C46—C51A—H51A119.2C113—C114—C115119.6 (2)
C50A—C51A—H51A119.2C113—C114—H114120.2
C51B—C50B—C49118.5 (8)C115—C114—H114120.2
C51B—C50B—H50B120.7C114—C115—C116120.2 (2)
C49—C50B—H50B120.7C114—C115—H115119.9
C50B—C51B—C46120.0 (8)C116—C115—H115119.9
C50B—C51B—H51B120.0C115—C116—C111120.4 (2)
C46—C51B—H51B120.0C115—C116—H116119.8
C37—N4—C45111.46 (18)C111—C116—H116119.8
C37—N4—C52122.88 (19)S1—Ag3—S3126.936 (19)
C45—N4—C52125.64 (19)S1—Ag3—S2127.68 (2)
N4—C52—C53114.39 (19)S3—Ag3—S2103.957 (19)
N4—C52—H52A108.7C117—S1—Ag3100.90 (7)
C53—C52—H52A108.7N9—C117—S1177.8 (2)
N4—C52—H52B108.7C118—S2—Ag393.45 (8)
C53—C52—H52B108.7N10—C118—S2179.4 (3)
H52A—C52—H52B107.6C119—S3—Ag3105.56 (9)
C58—C53—C54118.9 (2)N11—C119—S3177.1 (2)
C58—C53—C52123.4 (2)C121—C120—H12A109.5
C54—C53—C52117.7 (2)C121—C120—H12B109.5
C55—C54—C53120.9 (3)H12A—C120—H12B109.5
C55—C54—H54119.5C121—C120—H12C109.5
C53—C54—H54119.5H12A—C120—H12C109.5
C56—C55—C54119.7 (3)H12B—C120—H12C109.5
C56—C55—H55120.1O1—C121—C120107.2 (4)
C54—C55—H55120.1O1—C121—H12D110.3
C55—C56—C57120.1 (3)C120—C121—H12D110.3
C55—C56—H56119.9O1—C121—H12E110.3
C57—C56—H56119.9C120—C121—H12E110.3
C56—C57—C58120.0 (3)H12D—C121—H12E108.5
C56—C57—H57120.0C121—O1—C122113.9 (4)
C58—C57—H57120.0O1—C122—C123107.7 (3)
C53—C58—C57120.3 (3)O1—C122—H12F110.2
C53—C58—H58119.9C123—C122—H12F110.2
C57—C58—H58119.9O1—C122—H12G110.2
C66—Ag2—C95172.01 (7)C123—C122—H12G110.2
C64—C59—C60120.02 (19)H12F—C122—H12G108.5
C64—C59—H59120.0C122—C123—H12H109.5
C60—C59—H59120.0C122—C123—H12I109.5
C61—C60—C59120.4 (2)H12H—C123—H12I109.5
C61—C60—H60119.8C122—C123—H12J109.5
C59—C60—H60119.8H12H—C123—H12J109.5
C60—C61—C62119.8 (2)H12I—C123—H12J109.5
C6—C1—C2—C31.1 (4)C46—C45—N4—C522.1 (3)
C1—C2—C3—C41.6 (5)C37—N4—C52—C5392.3 (3)
C2—C3—C4—C51.6 (5)C45—N4—C52—C5389.6 (3)
C3—C4—C5—C61.0 (5)N4—C52—C53—C581.2 (3)
C4—C5—C6—C10.4 (4)N4—C52—C53—C54179.9 (2)
C4—C5—C6—C7179.4 (3)C58—C53—C54—C551.6 (4)
C2—C1—C6—C50.5 (4)C52—C53—C54—C55177.4 (3)
C2—C1—C6—C7179.4 (2)C53—C54—C55—C560.7 (5)
C5—C6—C7—N1162.3 (2)C54—C55—C56—C571.0 (5)
C1—C6—C7—N117.5 (3)C55—C56—C57—C581.7 (5)
C6—C7—N1—C872.3 (3)C54—C53—C58—C570.8 (4)
C6—C7—N1—C989.5 (2)C52—C53—C58—C57178.1 (3)
C9—N1—C8—N22.0 (2)C56—C57—C58—C530.8 (5)
C7—N1—C8—N2165.95 (18)C64—C59—C60—C610.2 (3)
C9—N1—C8—Ag1169.00 (15)C59—C60—C61—C620.5 (3)
C7—N1—C8—Ag15.1 (3)C60—C61—C62—C630.6 (3)
C8—N1—C9—C161.1 (2)C61—C62—C63—C640.1 (3)
C7—N1—C9—C16164.48 (19)C60—C59—C64—C630.8 (3)
C8—N1—C9—C10179.9 (2)C60—C59—C64—C65176.41 (19)
C7—N1—C9—C1016.8 (3)C62—C63—C64—C590.8 (3)
C16—C9—C10—C11111.4 (3)C62—C63—C64—C65176.6 (2)
N1—C9—C10—C1167.0 (3)C59—C64—C65—N523.7 (3)
C16—C9—C10—C1566.5 (4)C63—C64—C65—N5158.98 (18)
N1—C9—C10—C15115.1 (3)C64—C65—N5—C6674.7 (2)
C15—C10—C11—C123.5 (4)C64—C65—N5—C67123.2 (2)
C9—C10—C11—C12178.5 (2)C67—N5—C66—N60.3 (2)
C10—C11—C12—C133.1 (5)C65—N5—C66—N6164.03 (16)
C11—C12—C13—C140.3 (6)C67—N5—C66—Ag2171.15 (13)
C12—C13—C14—C152.0 (7)C65—N5—C66—Ag224.5 (2)
C13—C14—C15—C101.5 (7)C66—N5—C67—C740.4 (2)
C11—C10—C15—C141.3 (5)C65—N5—C67—C74163.23 (17)
C9—C10—C15—C14179.3 (4)C66—N5—C67—C68178.55 (17)
N1—C9—C16—N20.3 (2)C65—N5—C67—C6817.8 (3)
C10—C9—C16—N2178.3 (2)C74—C67—C68—C7343.9 (3)
N1—C9—C16—C17177.8 (2)N5—C67—C68—C73137.5 (2)
C10—C9—C16—C173.7 (4)C74—C67—C68—C69135.4 (2)
C9—C16—C17—C2269.5 (4)N5—C67—C68—C6943.3 (3)
N2—C16—C17—C22108.2 (3)C73—C68—C69—C701.0 (3)
C9—C16—C17—C18113.1 (3)C67—C68—C69—C70179.74 (19)
N2—C16—C17—C1869.2 (3)C68—C69—C70—C710.8 (3)
C22—C17—C18—C191.6 (4)C69—C70—C71—C720.4 (3)
C16—C17—C18—C19179.0 (2)C70—C71—C72—C730.1 (3)
C17—C18—C19—C200.4 (4)C71—C72—C73—C680.3 (3)
C18—C19—C20—C211.6 (5)C69—C68—C73—C720.8 (3)
C19—C20—C21—C222.5 (6)C67—C68—C73—C72180.00 (19)
C18—C17—C22—C210.7 (5)N5—C67—C74—N60.3 (2)
C16—C17—C22—C21178.1 (3)C68—C67—C74—N6178.52 (19)
C20—C21—C22—C171.3 (6)N5—C67—C74—C75175.57 (19)
N1—C8—N2—C162.2 (2)C68—C67—C74—C755.6 (4)
Ag1—C8—N2—C16168.31 (16)C67—C74—C75—C7668.8 (3)
N1—C8—N2—C23173.7 (2)N6—C74—C75—C76115.9 (2)
Ag1—C8—N2—C233.2 (3)C67—C74—C75—C80112.0 (2)
C9—C16—N2—C81.6 (3)N6—C74—C75—C8063.3 (3)
C17—C16—N2—C8176.6 (2)C80—C75—C76—C771.3 (3)
C9—C16—N2—C23173.0 (2)C74—C75—C76—C77177.84 (19)
C17—C16—N2—C235.2 (3)C75—C76—C77—C780.3 (3)
C8—N2—C23—C24106.1 (2)C76—C77—C78—C790.8 (3)
C16—N2—C23—C2464.3 (3)C77—C78—C79—C801.0 (3)
N2—C23—C24—C25126.8 (2)C78—C79—C80—C750.0 (3)
N2—C23—C24—C2952.5 (3)C76—C75—C80—C791.1 (3)
C29—C24—C25—C261.2 (4)C74—C75—C80—C79178.06 (19)
C23—C24—C25—C26178.0 (3)N5—C66—N6—C740.1 (2)
C24—C25—C26—C270.6 (5)Ag2—C66—N6—C74170.99 (13)
C25—C26—C27—C281.3 (6)N5—C66—N6—C81177.12 (16)
C26—C27—C28—C290.2 (6)Ag2—C66—N6—C816.0 (3)
C27—C28—C29—C241.6 (5)C67—C74—N6—C660.1 (2)
C25—C24—C29—C282.3 (4)C75—C74—N6—C66176.22 (17)
C23—C24—C29—C28176.9 (3)C67—C74—N6—C81176.79 (17)
C35—C30—C31—C320.4 (5)C75—C74—N6—C816.9 (3)
C30—C31—C32—C330.8 (6)C66—N6—C81—C8293.6 (2)
C31—C32—C33—C340.5 (5)C74—N6—C81—C8283.0 (2)
C32—C33—C34—C351.1 (5)N6—C81—C82—C8394.5 (2)
C31—C30—C35—C342.0 (4)N6—C81—C82—C8785.3 (2)
C31—C30—C35—C36176.5 (3)C87—C82—C83—C841.7 (3)
C33—C34—C35—C302.3 (4)C81—C82—C83—C84178.2 (2)
C33—C34—C35—C36176.2 (3)C82—C83—C84—C850.2 (4)
C30—C35—C36—N352.4 (3)C83—C84—C85—C861.2 (4)
C34—C35—C36—N3129.1 (2)C84—C85—C86—C871.2 (4)
C35—C36—N3—C3765.3 (3)C85—C86—C87—C820.2 (4)
C35—C36—N3—C38111.4 (2)C83—C82—C87—C861.7 (3)
C38—N3—C37—N41.0 (2)C81—C82—C87—C86178.1 (2)
C36—N3—C37—N4178.19 (18)C93—C88—C89—C900.7 (4)
C38—N3—C37—Ag1173.48 (14)C88—C89—C90—C910.5 (5)
C36—N3—C37—Ag13.7 (3)C89—C90—C91—C920.4 (5)
C37—N3—C38—C450.6 (2)C90—C91—C92—C930.4 (5)
C36—N3—C38—C45177.58 (19)C89—C88—C93—C920.7 (4)
C37—N3—C38—C39179.36 (19)C89—C88—C93—C94175.1 (2)
C36—N3—C38—C393.6 (3)C91—C92—C93—C880.5 (4)
C45—C38—C39—C4459.2 (3)C91—C92—C93—C94175.4 (3)
N3—C38—C39—C44122.3 (2)C88—C93—C94—N738.4 (3)
C45—C38—C39—C40119.5 (3)C92—C93—C94—N7145.8 (2)
N3—C38—C39—C4059.0 (3)C93—C94—N7—C9591.0 (2)
C44—C39—C40—C410.8 (4)C93—C94—N7—C9687.2 (2)
C38—C39—C40—C41179.6 (2)C96—N7—C95—N81.4 (2)
C39—C40—C41—C420.1 (4)C94—N7—C95—N8177.10 (16)
C40—C41—C42—C430.6 (4)C96—N7—C95—Ag2167.96 (14)
C41—C42—C43—C440.6 (5)C94—N7—C95—Ag213.6 (3)
C42—C43—C44—C390.1 (5)C95—N7—C96—C1031.5 (2)
C40—C39—C44—C430.8 (4)C94—N7—C96—C103176.87 (18)
C38—C39—C44—C43179.5 (2)C95—N7—C96—C97169.15 (19)
N3—C38—C45—N40.1 (2)C94—N7—C96—C9712.5 (3)
C39—C38—C45—N4178.6 (2)C103—C96—C97—C98137.9 (2)
N3—C38—C45—C46175.4 (2)N7—C96—C97—C9853.6 (3)
C39—C38—C45—C463.3 (4)C103—C96—C97—C10243.7 (3)
C38—C45—C46—C51A82.0 (7)N7—C96—C97—C102124.9 (2)
N4—C45—C46—C51A103.5 (7)C102—C97—C98—C992.2 (3)
C38—C45—C46—C47A96.2 (7)C96—C97—C98—C99176.3 (2)
N4—C45—C46—C47A78.3 (7)C97—C98—C99—C1001.5 (4)
C38—C45—C46—C47B63.6 (8)C98—C99—C100—C1010.6 (4)
N4—C45—C46—C47B110.8 (7)C99—C100—C101—C1022.0 (4)
C38—C45—C46—C51B110.3 (8)C98—C97—C102—C1010.7 (3)
N4—C45—C46—C51B75.2 (8)C96—C97—C102—C101177.8 (2)
C51A—C46—C47A—C48A1.6 (9)C100—C101—C102—C971.3 (4)
C47B—C46—C47A—C48A69.1 (10)N7—C96—C103—N81.0 (2)
C51B—C46—C47A—C48A28.6 (9)C97—C96—C103—N8169.28 (19)
C45—C46—C47A—C48A176.6 (5)N7—C96—C103—C104178.8 (2)
C46—C47A—C48A—C490.2 (10)C97—C96—C103—C1048.5 (4)
C51A—C46—C47B—C48B26.2 (9)C96—C103—C104—C10976.7 (3)
C47A—C46—C47B—C48B95.3 (12)N8—C103—C104—C109105.8 (3)
C51B—C46—C47B—C48B1.8 (10)C96—C103—C104—C10599.7 (3)
C45—C46—C47B—C48B176.0 (6)N8—C103—C104—C10577.8 (3)
C46—C47B—C48B—C492.2 (12)C109—C104—C105—C1060.8 (3)
C47B—C48B—C49—C50A30.1 (10)C103—C104—C105—C106175.7 (2)
C47B—C48B—C49—C50B5.1 (11)C104—C105—C106—C1070.6 (4)
C47B—C48B—C49—C48A77.0 (11)C105—C106—C107—C1080.0 (4)
C47A—C48A—C49—C48B84.6 (11)C106—C107—C108—C1090.5 (5)
C47A—C48A—C49—C50A2.2 (9)C107—C108—C109—C1040.3 (5)
C47A—C48A—C49—C50B28.6 (9)C105—C104—C109—C1080.3 (4)
C48B—C49—C50A—C51A29.5 (10)C103—C104—C109—C108176.1 (2)
C50B—C49—C50A—C51A89 (2)N7—C95—N8—C1030.7 (2)
C48A—C49—C50A—C51A2.3 (10)Ag2—C95—N8—C103168.99 (14)
C47A—C46—C51A—C50A1.5 (9)N7—C95—N8—C110176.58 (17)
C47B—C46—C51A—C50A27.0 (9)Ag2—C95—N8—C11013.7 (3)
C51B—C46—C51A—C50A88.1 (18)C96—C103—N8—C950.2 (2)
C45—C46—C51A—C50A176.6 (6)C104—C103—N8—C95178.16 (19)
C49—C50A—C51A—C460.6 (11)C96—C103—N8—C110177.40 (18)
C48B—C49—C50B—C51B3.8 (12)C104—C103—N8—C1104.6 (3)
C50A—C49—C50B—C51B77.2 (19)C95—N8—C110—C11182.2 (2)
C48A—C49—C50B—C51B28.1 (10)C103—N8—C110—C11194.7 (2)
C49—C50B—C51B—C460.4 (13)N8—C110—C111—C11616.9 (3)
C51A—C46—C51B—C50B77.3 (16)N8—C110—C111—C112165.55 (19)
C47A—C46—C51B—C50B29.3 (10)C116—C111—C112—C1131.7 (3)
C47B—C46—C51B—C50B3.0 (11)C110—C111—C112—C113175.9 (2)
C45—C46—C51B—C50B177.2 (7)C111—C112—C113—C1140.9 (4)
N3—C37—N4—C451.1 (2)C112—C113—C114—C1150.7 (4)
Ag1—C37—N4—C45173.29 (15)C113—C114—C115—C1161.4 (4)
N3—C37—N4—C52177.28 (18)C114—C115—C116—C1110.6 (4)
Ag1—C37—N4—C528.4 (3)C112—C111—C116—C1150.9 (3)
C38—C45—N4—C370.8 (2)C110—C111—C116—C115176.6 (2)
C46—C45—N4—C37176.21 (19)C120—C121—O1—C122177.1 (3)
C38—C45—N4—C52177.54 (19)C121—O1—C122—C123177.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C31—H31···O10.952.573.361 (4)141
C32—H32···N10i0.952.433.327 (4)157
C40—H40···S1ii0.952.823.684 (2)152
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y, z1.
Bis(µ-1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-κ2Se:Se)bis[bromido(1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-κSe)silver(I)] dichloromethane hexasolvate (2) top
Crystal data top
[Ag2Br2(C29H24N2Se)4]·6CH2Cl2Z = 1
Mr = 2802.96F(000) = 1400
Triclinic, P1Dx = 1.589 Mg m3
a = 13.6265 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.7422 (1) ÅCell parameters from 42526 reflections
c = 16.9397 (2) Åθ = 3.0–26.4°
α = 106.4172 (7)°µ = 2.58 mm1
β = 112.2820 (8)°T = 150 K
γ = 96.2211 (6)°Prism, clear pale yellow
V = 2930.04 (5) Å30.37 × 0.26 × 0.20 mm
Data collection top
Rigaku SuperNova, Dual, Cu at zero, Atlas
diffractometer
12002 independent reflections
Radiation source: micro-focus sealed X-ray tube10726 reflections with I > 2σ(I)
Detector resolution: 10.3196 pixels mm-1Rint = 0.037
ω scansθmax = 26.4°, θmin = 2.8°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 1717
Tmin = 0.517, Tmax = 0.664k = 1818
119415 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0468P)2 + 5.4618P]
where P = (Fo2 + 2Fc2)/3
12002 reflections(Δ/σ)max = 0.002
654 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 1.48 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.

Refinement. The PLATON SQUEEZE procedure (A. L. Spek. Acta Cryst. C71, 2015, 9-18) was used to treat regions of disordered solvent which could not be modelled in terms of atomic sites. The number of electrons found in these regions, 84, was assigned to 2 molecules of dichloromethane. 2 dichloromethanes would give 84 electrons.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.2991 (3)0.2585 (2)0.5958 (2)0.0303 (6)
H10.36860.24530.62240.036*
C20.2264 (3)0.2008 (3)0.5078 (2)0.0390 (8)
H20.24600.14830.47430.047*
C30.1255 (3)0.2194 (3)0.4687 (3)0.0476 (9)
H30.07520.17960.40830.057*
C40.0978 (3)0.2950 (3)0.5167 (3)0.0530 (10)
H40.02830.30780.48940.064*
C50.1709 (3)0.3540 (3)0.6060 (3)0.0422 (8)
H50.15090.40650.63900.051*
C60.2721 (2)0.3356 (2)0.6459 (2)0.0281 (6)
C70.3529 (2)0.3973 (2)0.7424 (2)0.0277 (6)
H7A0.32010.44770.76800.033*
H7B0.36770.35550.78010.033*
N10.45650 (19)0.44492 (16)0.74753 (15)0.0228 (5)
C80.5529 (2)0.42207 (19)0.78510 (18)0.0227 (5)
Se10.57786 (3)0.32825 (2)0.83916 (2)0.02863 (8)
C90.4711 (2)0.52088 (19)0.71564 (18)0.0232 (5)
C100.3796 (2)0.5572 (2)0.66477 (19)0.0246 (6)
C110.3552 (3)0.5471 (2)0.5752 (2)0.0351 (7)
H110.39980.51970.54810.042*
C120.2666 (3)0.5764 (3)0.5246 (2)0.0444 (9)
H120.25070.56910.46320.053*
C130.2019 (3)0.6158 (3)0.5630 (3)0.0462 (9)
H130.14140.63620.52830.055*
C140.2241 (4)0.6259 (3)0.6511 (3)0.0519 (10)
H140.17810.65210.67710.062*
C150.3137 (3)0.5981 (3)0.7029 (2)0.0412 (8)
H150.33000.60700.76470.049*
C160.5788 (2)0.54519 (19)0.73583 (18)0.0227 (5)
C170.6406 (2)0.6262 (2)0.72556 (19)0.0252 (6)
C180.6984 (3)0.6095 (2)0.6728 (2)0.0329 (7)
H180.69780.54460.64180.039*
C190.7568 (3)0.6868 (3)0.6651 (3)0.0418 (8)
H190.79590.67490.62880.050*
C200.7583 (3)0.7811 (3)0.7102 (3)0.0441 (8)
H200.79910.83410.70550.053*
C210.7003 (3)0.7986 (2)0.7623 (3)0.0436 (8)
H210.70110.86380.79290.052*
C220.6411 (3)0.7217 (2)0.7702 (2)0.0331 (7)
H220.60110.73400.80580.040*
N20.62857 (19)0.48262 (16)0.77814 (15)0.0220 (5)
C230.7469 (2)0.4912 (2)0.82079 (19)0.0267 (6)
H23A0.76440.46990.87390.032*
H23B0.78520.56080.84390.032*
C240.7915 (2)0.4329 (2)0.75860 (19)0.0273 (6)
C250.7432 (3)0.3347 (2)0.7062 (2)0.0311 (6)
H250.67730.30420.70500.037*
C260.7911 (3)0.2812 (3)0.6557 (2)0.0387 (7)
H260.75800.21420.62060.046*
C270.8863 (3)0.3247 (3)0.6561 (2)0.0393 (8)
H270.91870.28750.62160.047*
C280.9342 (3)0.4220 (3)0.7065 (2)0.0413 (8)
H280.99960.45240.70690.050*
C290.8862 (3)0.4759 (3)0.7571 (2)0.0351 (7)
H290.91900.54320.79120.042*
C300.5585 (3)0.1771 (3)1.0909 (2)0.0491 (9)
H300.62020.22401.10180.059*
C310.5587 (4)0.1424 (4)1.1588 (3)0.0648 (13)
H310.61990.16661.21670.078*
C320.4709 (4)0.0730 (3)1.1427 (3)0.0563 (12)
H320.47210.04741.18850.068*
C330.3819 (4)0.0412 (3)1.0607 (3)0.0651 (13)
H330.31990.00521.04980.078*
C340.3818 (4)0.0765 (3)0.9930 (3)0.0558 (11)
H340.31970.05310.93560.067*
C350.4684 (3)0.1437 (2)1.00705 (19)0.0283 (6)
C360.4722 (2)0.1824 (2)0.93410 (18)0.0236 (5)
H36A0.53240.24190.96260.028*
H36B0.48780.13310.89000.028*
N30.36874 (18)0.20544 (16)0.88532 (14)0.0195 (4)
C370.3351 (2)0.28258 (19)0.92241 (17)0.0208 (5)
Se20.41926 (2)0.38665 (2)1.03116 (2)0.02432 (7)
C380.2820 (2)0.14190 (19)0.80476 (17)0.0208 (5)
C390.2888 (2)0.0524 (2)0.74254 (18)0.0222 (5)
C400.3653 (2)0.0541 (2)0.7071 (2)0.0280 (6)
H400.41780.11290.72580.034*
C410.3649 (3)0.0308 (2)0.6440 (2)0.0344 (7)
H410.41750.02970.61990.041*
C420.2887 (3)0.1161 (2)0.6165 (2)0.0348 (7)
H420.28870.17360.57330.042*
C430.2124 (3)0.1183 (2)0.6515 (2)0.0315 (7)
H430.16010.17730.63250.038*
C440.2119 (2)0.0345 (2)0.71439 (19)0.0261 (6)
H440.15920.03620.73830.031*
C450.1938 (2)0.18073 (19)0.79410 (18)0.0217 (5)
C460.0815 (2)0.14143 (19)0.72006 (18)0.0224 (5)
C470.0640 (2)0.1324 (2)0.63145 (19)0.0273 (6)
H470.12290.15500.61940.033*
C480.0397 (3)0.0901 (2)0.5609 (2)0.0336 (7)
H480.05210.08470.50040.040*
C490.1246 (3)0.0560 (2)0.5781 (2)0.0359 (7)
H490.19540.02680.52940.043*
C500.1075 (3)0.0638 (2)0.6657 (2)0.0358 (7)
H500.16640.03950.67690.043*
C510.0047 (2)0.1073 (2)0.7372 (2)0.0301 (6)
H510.00680.11360.79760.036*
N40.22814 (18)0.26809 (16)0.86718 (15)0.0210 (4)
C520.1591 (2)0.3352 (2)0.87987 (19)0.0236 (5)
H52A0.10310.32880.81930.028*
H52B0.20480.40280.90880.028*
C530.1023 (2)0.3184 (2)0.93731 (19)0.0262 (6)
C540.1310 (3)0.2618 (2)0.9917 (2)0.0325 (7)
H540.18740.22900.99220.039*
C550.0770 (3)0.2531 (3)1.0453 (2)0.0434 (8)
H550.09620.21391.08200.052*
C560.0046 (3)0.3012 (3)1.0454 (3)0.0464 (9)
H560.04070.29561.08270.056*
C570.0336 (3)0.3573 (3)0.9915 (3)0.0463 (9)
H570.08980.39030.99140.056*
C580.0191 (3)0.3656 (3)0.9375 (2)0.0375 (7)
H580.00170.40400.90010.045*
Ag0.59867 (2)0.44437 (2)1.00177 (2)0.03306 (7)
Br0.77487 (3)0.41077 (3)1.11754 (2)0.04318 (9)
C590.4858 (4)0.7506 (4)0.5306 (3)0.0671 (13)
H59A0.53890.76340.59410.081*
H59B0.41150.73980.52810.081*
Cl10.49731 (8)0.64544 (7)0.45851 (6)0.0459 (2)
Cl20.50991 (12)0.85328 (9)0.50091 (11)0.0817 (4)
C600.7655 (4)0.1514 (3)0.8195 (3)0.0628 (12)
H60A0.74390.19610.86230.075*0.898 (4)
H60B0.81570.19140.80580.075*0.898 (4)
H60C0.79120.21670.81920.075*0.102 (4)
H60D0.82530.11730.82710.075*0.102 (4)
Cl30.64844 (9)0.08367 (10)0.71812 (10)0.0764 (4)
Cl4A0.83340 (11)0.07387 (9)0.87093 (9)0.0670 (5)0.898 (4)
Cl4B0.7203 (18)0.1617 (16)0.9129 (15)0.120 (7)*0.102 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0294 (15)0.0298 (15)0.0306 (15)0.0035 (12)0.0132 (13)0.0099 (12)
C20.0415 (19)0.0386 (18)0.0322 (17)0.0023 (14)0.0181 (15)0.0073 (14)
C30.041 (2)0.055 (2)0.0329 (18)0.0089 (17)0.0050 (16)0.0178 (17)
C40.0272 (18)0.057 (2)0.064 (3)0.0042 (16)0.0014 (17)0.032 (2)
C50.0316 (17)0.0375 (18)0.056 (2)0.0100 (14)0.0151 (16)0.0194 (16)
C60.0261 (15)0.0273 (14)0.0339 (16)0.0040 (11)0.0143 (13)0.0138 (12)
C70.0294 (15)0.0283 (14)0.0292 (15)0.0058 (12)0.0173 (13)0.0094 (12)
N10.0287 (12)0.0201 (11)0.0191 (11)0.0052 (9)0.0111 (10)0.0054 (9)
C80.0306 (15)0.0183 (12)0.0171 (12)0.0058 (11)0.0103 (11)0.0030 (10)
Se10.04242 (18)0.02315 (14)0.02676 (15)0.01194 (12)0.01801 (13)0.01214 (12)
C90.0297 (15)0.0211 (13)0.0175 (12)0.0055 (11)0.0101 (11)0.0053 (10)
C100.0269 (14)0.0212 (13)0.0252 (14)0.0067 (11)0.0115 (12)0.0068 (11)
C110.0392 (18)0.0455 (18)0.0283 (16)0.0242 (15)0.0173 (14)0.0147 (14)
C120.048 (2)0.054 (2)0.0320 (17)0.0304 (18)0.0127 (16)0.0164 (16)
C130.041 (2)0.047 (2)0.057 (2)0.0287 (17)0.0187 (18)0.0240 (18)
C140.061 (2)0.057 (2)0.068 (3)0.042 (2)0.045 (2)0.032 (2)
C150.059 (2)0.0440 (19)0.0388 (18)0.0285 (17)0.0317 (17)0.0190 (15)
C160.0283 (14)0.0220 (13)0.0169 (12)0.0072 (11)0.0090 (11)0.0060 (10)
C170.0267 (14)0.0259 (14)0.0211 (13)0.0065 (11)0.0067 (11)0.0107 (11)
C180.0386 (17)0.0327 (16)0.0321 (16)0.0095 (13)0.0182 (14)0.0134 (13)
C190.044 (2)0.047 (2)0.048 (2)0.0112 (16)0.0277 (17)0.0258 (17)
C200.0414 (19)0.0384 (18)0.056 (2)0.0012 (15)0.0201 (17)0.0258 (17)
C210.051 (2)0.0247 (16)0.050 (2)0.0044 (14)0.0191 (18)0.0113 (15)
C220.0392 (17)0.0256 (15)0.0346 (17)0.0069 (13)0.0166 (14)0.0102 (13)
N20.0263 (12)0.0204 (11)0.0182 (11)0.0069 (9)0.0085 (9)0.0063 (9)
C230.0255 (14)0.0277 (14)0.0185 (13)0.0042 (11)0.0031 (11)0.0059 (11)
C240.0247 (14)0.0347 (15)0.0221 (14)0.0121 (12)0.0058 (11)0.0133 (12)
C250.0315 (16)0.0305 (15)0.0330 (16)0.0108 (12)0.0140 (13)0.0120 (13)
C260.0450 (19)0.0378 (17)0.0352 (17)0.0201 (15)0.0166 (15)0.0127 (14)
C270.0399 (18)0.054 (2)0.0351 (17)0.0282 (16)0.0193 (15)0.0210 (16)
C280.0298 (17)0.062 (2)0.0378 (18)0.0155 (16)0.0146 (15)0.0229 (17)
C290.0288 (16)0.0428 (18)0.0293 (16)0.0059 (13)0.0086 (13)0.0128 (14)
C300.038 (2)0.080 (3)0.0338 (18)0.0264 (19)0.0095 (16)0.0301 (19)
C310.064 (3)0.106 (4)0.040 (2)0.045 (3)0.017 (2)0.046 (2)
C320.104 (4)0.054 (2)0.041 (2)0.054 (3)0.041 (2)0.0347 (19)
C330.096 (4)0.051 (2)0.046 (2)0.004 (2)0.030 (2)0.024 (2)
C340.070 (3)0.050 (2)0.0279 (18)0.0117 (19)0.0063 (18)0.0170 (16)
C350.0396 (17)0.0255 (14)0.0216 (14)0.0170 (12)0.0115 (13)0.0096 (11)
C360.0210 (13)0.0240 (13)0.0201 (13)0.0064 (10)0.0026 (11)0.0080 (11)
N30.0195 (11)0.0202 (11)0.0158 (10)0.0044 (8)0.0049 (9)0.0060 (9)
C370.0234 (13)0.0202 (12)0.0154 (12)0.0034 (10)0.0061 (10)0.0054 (10)
Se20.02608 (15)0.02286 (14)0.01577 (13)0.00262 (11)0.00472 (11)0.00219 (10)
C380.0199 (13)0.0222 (13)0.0154 (12)0.0030 (10)0.0035 (10)0.0062 (10)
C390.0215 (13)0.0240 (13)0.0156 (12)0.0093 (10)0.0020 (10)0.0062 (10)
C400.0247 (14)0.0323 (15)0.0244 (14)0.0096 (12)0.0077 (12)0.0093 (12)
C410.0331 (16)0.0427 (18)0.0276 (15)0.0167 (14)0.0142 (13)0.0084 (13)
C420.0388 (17)0.0315 (16)0.0228 (15)0.0169 (13)0.0053 (13)0.0012 (12)
C430.0307 (16)0.0229 (14)0.0270 (15)0.0073 (12)0.0012 (12)0.0041 (12)
C440.0258 (14)0.0253 (14)0.0221 (13)0.0068 (11)0.0053 (11)0.0080 (11)
C450.0233 (13)0.0209 (13)0.0164 (12)0.0044 (10)0.0055 (11)0.0049 (10)
C460.0202 (13)0.0210 (13)0.0200 (13)0.0074 (10)0.0036 (11)0.0050 (10)
C470.0294 (15)0.0276 (14)0.0213 (14)0.0084 (12)0.0071 (12)0.0082 (11)
C480.0373 (17)0.0317 (16)0.0198 (14)0.0104 (13)0.0013 (13)0.0064 (12)
C490.0260 (15)0.0278 (15)0.0321 (16)0.0048 (12)0.0040 (13)0.0031 (13)
C500.0234 (15)0.0359 (17)0.0383 (18)0.0030 (12)0.0079 (13)0.0083 (14)
C510.0265 (15)0.0343 (16)0.0253 (15)0.0063 (12)0.0093 (12)0.0076 (12)
N40.0216 (11)0.0202 (11)0.0175 (11)0.0054 (9)0.0059 (9)0.0046 (9)
C520.0249 (14)0.0214 (13)0.0221 (13)0.0094 (11)0.0080 (11)0.0057 (11)
C530.0246 (14)0.0258 (14)0.0197 (13)0.0034 (11)0.0065 (11)0.0014 (11)
C540.0337 (16)0.0324 (16)0.0297 (16)0.0061 (13)0.0127 (13)0.0107 (13)
C550.047 (2)0.045 (2)0.0382 (19)0.0003 (16)0.0190 (16)0.0175 (16)
C560.042 (2)0.051 (2)0.0402 (19)0.0052 (16)0.0238 (17)0.0052 (16)
C570.0378 (19)0.050 (2)0.048 (2)0.0116 (16)0.0242 (17)0.0057 (17)
C580.0346 (17)0.0434 (19)0.0366 (18)0.0158 (14)0.0170 (15)0.0125 (15)
Ag0.03885 (14)0.03004 (12)0.02210 (12)0.00221 (10)0.00806 (10)0.00678 (9)
Br0.03466 (18)0.0598 (2)0.03813 (19)0.01376 (16)0.01402 (15)0.02296 (16)
C590.078 (3)0.079 (3)0.044 (2)0.035 (3)0.031 (2)0.008 (2)
Cl10.0467 (5)0.0523 (5)0.0417 (5)0.0182 (4)0.0221 (4)0.0143 (4)
Cl20.0795 (8)0.0507 (6)0.1100 (11)0.0188 (6)0.0553 (8)0.0001 (6)
C600.056 (3)0.046 (2)0.070 (3)0.0032 (19)0.023 (2)0.006 (2)
Cl30.0393 (6)0.0724 (8)0.0863 (9)0.0018 (5)0.0126 (6)0.0080 (6)
Cl4A0.0709 (9)0.0580 (8)0.0583 (8)0.0081 (6)0.0150 (6)0.0272 (6)
Geometric parameters (Å, º) top
C1—C21.381 (5)C33—C341.387 (5)
C1—C61.390 (4)C33—H330.9500
C1—H10.9500C34—C351.352 (5)
C2—C31.379 (5)C34—H340.9500
C2—H20.9500C35—C361.515 (4)
C3—C41.362 (6)C36—N31.471 (3)
C3—H30.9500C36—H36A0.9900
C4—C51.400 (6)C36—H36B0.9900
C4—H40.9500N3—C371.351 (3)
C5—C61.383 (5)N3—C381.397 (3)
C5—H50.9500C37—N41.353 (3)
C6—C71.512 (4)C37—Se21.866 (3)
C7—N11.466 (4)Se2—Agi2.7187 (4)
C7—H7A0.9900Se2—Ag2.7677 (4)
C7—H7B0.9900C38—C451.359 (4)
N1—C81.352 (4)C38—C391.475 (4)
N1—C91.400 (3)C39—C401.386 (4)
C8—N21.351 (4)C39—C441.397 (4)
C8—Se11.857 (3)C40—C411.395 (4)
Se1—Ag2.6899 (4)C40—H400.9500
C9—C161.354 (4)C41—C421.377 (5)
C9—C101.475 (4)C41—H410.9500
C10—C111.384 (4)C42—C431.380 (5)
C10—C151.386 (4)C42—H420.9500
C11—C121.384 (4)C43—C441.387 (4)
C11—H110.9500C43—H430.9500
C12—C131.368 (5)C44—H440.9500
C12—H120.9500C45—N41.392 (3)
C13—C141.365 (6)C45—C461.481 (4)
C13—H130.9500C46—C511.389 (4)
C14—C151.389 (5)C46—C471.392 (4)
C14—H140.9500C47—C481.387 (4)
C15—H150.9500C47—H470.9500
C16—N21.402 (3)C48—C491.374 (5)
C16—C171.476 (4)C48—H480.9500
C17—C181.389 (4)C49—C501.380 (5)
C17—C221.396 (4)C49—H490.9500
C18—C191.384 (5)C50—C511.386 (4)
C18—H180.9500C50—H500.9500
C19—C201.377 (5)C51—H510.9500
C19—H190.9500N4—C521.465 (3)
C20—C211.384 (5)C52—C531.507 (4)
C20—H200.9500C52—H52A0.9900
C21—C221.387 (5)C52—H52B0.9900
C21—H210.9500C53—C541.389 (4)
C22—H220.9500C53—C581.395 (4)
N2—C231.469 (4)C54—C551.392 (5)
C23—C241.518 (4)C54—H540.9500
C23—H23A0.9900C55—C561.383 (6)
C23—H23B0.9900C55—H550.9500
C24—C291.387 (4)C56—C571.378 (6)
C24—C251.393 (4)C56—H560.9500
C25—C261.391 (5)C57—C581.381 (5)
C25—H250.9500C57—H570.9500
C26—C271.381 (5)C58—H580.9500
C26—H260.9500Ag—Br2.6631 (4)
C27—C281.377 (5)Ag—Se2i2.7186 (4)
C27—H270.9500C59—Cl11.746 (4)
C28—C291.395 (5)C59—Cl21.761 (6)
C28—H280.9500C59—H59A0.9900
C29—H290.9500C59—H59B0.9900
C30—C311.384 (6)C60—Cl31.760 (5)
C30—C351.385 (5)C60—Cl4A1.762 (5)
C30—H300.9500C60—Cl4B1.88 (2)
C31—C321.372 (7)C60—H60A0.9900
C31—H310.9500C60—H60B0.9900
C32—C331.360 (7)C60—H60C0.9900
C32—H320.9500C60—H60D0.9900
C2—C1—C6120.9 (3)C35—C34—H34119.4
C2—C1—H1119.5C33—C34—H34119.4
C6—C1—H1119.5C34—C35—C30118.8 (3)
C3—C2—C1119.9 (3)C34—C35—C36122.7 (3)
C3—C2—H2120.0C30—C35—C36118.4 (3)
C1—C2—H2120.0N3—C36—C35112.0 (2)
C4—C3—C2119.9 (3)N3—C36—H36A109.2
C4—C3—H3120.0C35—C36—H36A109.2
C2—C3—H3120.0N3—C36—H36B109.2
C3—C4—C5120.7 (3)C35—C36—H36B109.2
C3—C4—H4119.7H36A—C36—H36B107.9
C5—C4—H4119.7C37—N3—C38109.6 (2)
C6—C5—C4119.8 (4)C37—N3—C36123.6 (2)
C6—C5—H5120.1C38—N3—C36125.3 (2)
C4—C5—H5120.1N3—C37—N4106.8 (2)
C5—C6—C1118.7 (3)N3—C37—Se2126.4 (2)
C5—C6—C7121.4 (3)N4—C37—Se2126.8 (2)
C1—C6—C7119.8 (3)C37—Se2—Agi108.43 (8)
N1—C7—C6112.7 (2)C37—Se2—Ag100.72 (8)
N1—C7—H7A109.1Agi—Se2—Ag73.649 (11)
C6—C7—H7A109.1C45—C38—N3106.9 (2)
N1—C7—H7B109.1C45—C38—C39127.7 (2)
C6—C7—H7B109.1N3—C38—C39125.4 (2)
H7A—C7—H7B107.8C40—C39—C44119.5 (3)
C8—N1—C9109.8 (2)C40—C39—C38121.4 (3)
C8—N1—C7124.5 (2)C44—C39—C38118.9 (3)
C9—N1—C7125.7 (2)C39—C40—C41119.9 (3)
N2—C8—N1106.8 (2)C39—C40—H40120.1
N2—C8—Se1126.4 (2)C41—C40—H40120.1
N1—C8—Se1126.8 (2)C42—C41—C40120.3 (3)
C8—Se1—Ag94.72 (8)C42—C41—H41119.9
C16—C9—N1106.7 (2)C40—C41—H41119.9
C16—C9—C10130.3 (3)C41—C42—C43120.2 (3)
N1—C9—C10122.8 (3)C41—C42—H42119.9
C11—C10—C15118.5 (3)C43—C42—H42119.9
C11—C10—C9119.6 (3)C42—C43—C44120.2 (3)
C15—C10—C9121.9 (3)C42—C43—H43119.9
C10—C11—C12120.7 (3)C44—C43—H43119.9
C10—C11—H11119.6C43—C44—C39120.0 (3)
C12—C11—H11119.6C43—C44—H44120.0
C13—C12—C11120.1 (3)C39—C44—H44120.0
C13—C12—H12120.0C38—C45—N4106.9 (2)
C11—C12—H12120.0C38—C45—C46128.4 (2)
C14—C13—C12120.2 (3)N4—C45—C46124.7 (2)
C14—C13—H13119.9C51—C46—C47119.9 (3)
C12—C13—H13119.9C51—C46—C45120.6 (3)
C13—C14—C15120.2 (3)C47—C46—C45119.3 (3)
C13—C14—H14119.9C48—C47—C46119.7 (3)
C15—C14—H14119.9C48—C47—H47120.2
C10—C15—C14120.3 (3)C46—C47—H47120.2
C10—C15—H15119.8C49—C48—C47120.2 (3)
C14—C15—H15119.8C49—C48—H48119.9
C9—C16—N2107.2 (2)C47—C48—H48119.9
C9—C16—C17129.5 (3)C48—C49—C50120.4 (3)
N2—C16—C17123.1 (2)C48—C49—H49119.8
C18—C17—C22119.4 (3)C50—C49—H49119.8
C18—C17—C16121.6 (3)C49—C50—C51120.2 (3)
C22—C17—C16119.0 (3)C49—C50—H50119.9
C19—C18—C17120.5 (3)C51—C50—H50119.9
C19—C18—H18119.8C50—C51—C46119.6 (3)
C17—C18—H18119.8C50—C51—H51120.2
C20—C19—C18120.0 (3)C46—C51—H51120.2
C20—C19—H19120.0C37—N4—C45109.7 (2)
C18—C19—H19120.0C37—N4—C52125.6 (2)
C19—C20—C21120.1 (3)C45—N4—C52124.7 (2)
C19—C20—H20120.0N4—C52—C53114.1 (2)
C21—C20—H20120.0N4—C52—H52A108.7
C20—C21—C22120.4 (3)C53—C52—H52A108.7
C20—C21—H21119.8N4—C52—H52B108.7
C22—C21—H21119.8C53—C52—H52B108.7
C21—C22—C17119.6 (3)H52A—C52—H52B107.6
C21—C22—H22120.2C54—C53—C58118.9 (3)
C17—C22—H22120.2C54—C53—C52123.7 (3)
C8—N2—C16109.5 (2)C58—C53—C52117.3 (3)
C8—N2—C23124.8 (2)C53—C54—C55119.9 (3)
C16—N2—C23125.1 (2)C53—C54—H54120.0
N2—C23—C24115.0 (2)C55—C54—H54120.0
N2—C23—H23A108.5C56—C55—C54120.4 (3)
C24—C23—H23A108.5C56—C55—H55119.8
N2—C23—H23B108.5C54—C55—H55119.8
C24—C23—H23B108.5C57—C56—C55120.0 (3)
H23A—C23—H23B107.5C57—C56—H56120.0
C29—C24—C25118.5 (3)C55—C56—H56120.0
C29—C24—C23119.8 (3)C56—C57—C58120.0 (3)
C25—C24—C23121.6 (3)C56—C57—H57120.0
C26—C25—C24120.2 (3)C58—C57—H57120.0
C26—C25—H25119.9C57—C58—C53120.8 (3)
C24—C25—H25119.9C57—C58—H58119.6
C27—C26—C25120.7 (3)C53—C58—H58119.6
C27—C26—H26119.7Br—Ag—Se1102.274 (13)
C25—C26—H26119.7Br—Ag—Se2i126.883 (14)
C28—C27—C26119.8 (3)Se1—Ag—Se2i100.026 (11)
C28—C27—H27120.1Br—Ag—Se2109.628 (12)
C26—C27—H27120.1Se1—Ag—Se2110.623 (12)
C27—C28—C29119.7 (3)Se2i—Ag—Se2106.352 (11)
C27—C28—H28120.2Cl1—C59—Cl2112.3 (3)
C29—C28—H28120.2Cl1—C59—H59A109.1
C24—C29—C28121.2 (3)Cl2—C59—H59A109.1
C24—C29—H29119.4Cl1—C59—H59B109.1
C28—C29—H29119.4Cl2—C59—H59B109.1
C31—C30—C35120.1 (4)H59A—C59—H59B107.9
C31—C30—H30119.9Cl3—C60—Cl4A110.9 (2)
C35—C30—H30119.9Cl3—C60—Cl4B104.9 (7)
C32—C31—C30120.2 (4)Cl3—C60—H60A109.5
C32—C31—H31119.9Cl4A—C60—H60A109.5
C30—C31—H31119.9Cl3—C60—H60B109.5
C33—C32—C31119.5 (4)Cl4A—C60—H60B109.5
C33—C32—H32120.2H60A—C60—H60B108.0
C31—C32—H32120.2Cl3—C60—H60C110.8
C32—C33—C34120.0 (4)Cl4B—C60—H60C110.8
C32—C33—H33120.0Cl3—C60—H60D110.8
C34—C33—H33120.0Cl4B—C60—H60D110.8
C35—C34—C33121.2 (4)H60C—C60—H60D108.8
C6—C1—C2—C30.0 (5)C30—C31—C32—C332.3 (7)
C1—C2—C3—C40.3 (5)C31—C32—C33—C342.0 (7)
C2—C3—C4—C50.3 (6)C32—C33—C34—C351.0 (8)
C3—C4—C5—C60.1 (6)C33—C34—C35—C300.1 (6)
C4—C5—C6—C10.2 (5)C33—C34—C35—C36178.7 (4)
C4—C5—C6—C7179.6 (3)C31—C30—C35—C340.4 (6)
C2—C1—C6—C50.2 (5)C31—C30—C35—C36179.0 (4)
C2—C1—C6—C7179.6 (3)C34—C35—C36—N344.2 (4)
C5—C6—C7—N1120.5 (3)C30—C35—C36—N3137.3 (3)
C1—C6—C7—N159.7 (4)C35—C36—N3—C3772.1 (3)
C6—C7—N1—C8111.0 (3)C35—C36—N3—C3892.7 (3)
C6—C7—N1—C969.7 (3)C38—N3—C37—N40.8 (3)
C9—N1—C8—N20.4 (3)C36—N3—C37—N4166.1 (2)
C7—N1—C8—N2179.0 (2)C38—N3—C37—Se2178.82 (19)
C9—N1—C8—Se1178.68 (19)C36—N3—C37—Se211.9 (4)
C7—N1—C8—Se10.7 (4)N3—C37—Se2—Agi128.8 (2)
N2—C8—Se1—Ag94.9 (2)N4—C37—Se2—Agi53.6 (2)
N1—C8—Se1—Ag83.1 (2)N3—C37—Se2—Ag52.6 (2)
C8—N1—C9—C161.0 (3)N4—C37—Se2—Ag129.7 (2)
C7—N1—C9—C16178.4 (2)C37—N3—C38—C451.2 (3)
C8—N1—C9—C10175.2 (2)C36—N3—C38—C45165.5 (2)
C7—N1—C9—C105.5 (4)C37—N3—C38—C39176.5 (3)
C16—C9—C10—C1159.5 (4)C36—N3—C38—C3916.9 (4)
N1—C9—C10—C11115.8 (3)C45—C38—C39—C40123.0 (3)
C16—C9—C10—C15123.2 (4)N3—C38—C39—C4054.1 (4)
N1—C9—C10—C1561.6 (4)C45—C38—C39—C4452.8 (4)
C15—C10—C11—C120.5 (5)N3—C38—C39—C44130.1 (3)
C9—C10—C11—C12176.9 (3)C44—C39—C40—C410.1 (4)
C10—C11—C12—C130.0 (6)C38—C39—C40—C41176.0 (3)
C11—C12—C13—C140.3 (6)C39—C40—C41—C420.2 (5)
C12—C13—C14—C151.2 (7)C40—C41—C42—C430.3 (5)
C11—C10—C15—C141.4 (5)C41—C42—C43—C440.2 (5)
C9—C10—C15—C14176.0 (3)C42—C43—C44—C390.1 (4)
C13—C14—C15—C101.8 (6)C40—C39—C44—C430.1 (4)
N1—C9—C16—N21.2 (3)C38—C39—C44—C43176.0 (2)
C10—C9—C16—N2174.6 (3)N3—C38—C45—N41.0 (3)
N1—C9—C16—C17173.6 (3)C39—C38—C45—N4176.5 (3)
C10—C9—C16—C1710.6 (5)N3—C38—C45—C46179.5 (3)
C9—C16—C17—C18121.8 (3)C39—C38—C45—C462.9 (5)
N2—C16—C17—C1864.1 (4)C38—C45—C46—C51111.2 (3)
C9—C16—C17—C2258.3 (4)N4—C45—C46—C5169.5 (4)
N2—C16—C17—C22115.7 (3)C38—C45—C46—C4764.2 (4)
C22—C17—C18—C190.6 (5)N4—C45—C46—C47115.2 (3)
C16—C17—C18—C19179.3 (3)C51—C46—C47—C480.7 (4)
C17—C18—C19—C200.2 (5)C45—C46—C47—C48176.1 (3)
C18—C19—C20—C210.8 (6)C46—C47—C48—C491.0 (4)
C19—C20—C21—C220.5 (6)C47—C48—C49—C500.3 (5)
C20—C21—C22—C170.3 (5)C48—C49—C50—C510.7 (5)
C18—C17—C22—C210.9 (5)C49—C50—C51—C461.0 (5)
C16—C17—C22—C21179.0 (3)C47—C46—C51—C500.3 (4)
N1—C8—N2—C160.4 (3)C45—C46—C51—C50175.0 (3)
Se1—C8—N2—C16177.93 (19)N3—C37—N4—C450.1 (3)
N1—C8—N2—C23171.8 (2)Se2—C37—N4—C45178.15 (19)
Se1—C8—N2—C236.5 (4)N3—C37—N4—C52178.2 (2)
C9—C16—N2—C81.0 (3)Se2—C37—N4—C523.8 (4)
C17—C16—N2—C8174.2 (2)C38—C45—N4—C370.6 (3)
C9—C16—N2—C23172.4 (2)C46—C45—N4—C37180.0 (2)
C17—C16—N2—C232.8 (4)C38—C45—N4—C52177.5 (2)
C8—N2—C23—C2497.6 (3)C46—C45—N4—C522.0 (4)
C16—N2—C23—C2492.3 (3)C37—N4—C52—C5389.4 (3)
N2—C23—C24—C29134.4 (3)C45—N4—C52—C5392.9 (3)
N2—C23—C24—C2549.4 (4)N4—C52—C53—C5414.8 (4)
C29—C24—C25—C261.5 (4)N4—C52—C53—C58167.5 (3)
C23—C24—C25—C26174.7 (3)C58—C53—C54—C550.1 (5)
C24—C25—C26—C270.6 (5)C52—C53—C54—C55177.5 (3)
C25—C26—C27—C280.3 (5)C53—C54—C55—C560.5 (5)
C26—C27—C28—C290.2 (5)C54—C55—C56—C570.7 (6)
C25—C24—C29—C281.7 (5)C55—C56—C57—C580.1 (6)
C23—C24—C29—C28174.7 (3)C56—C57—C58—C530.5 (5)
C27—C28—C29—C240.8 (5)C54—C53—C58—C570.7 (5)
C35—C30—C31—C321.5 (7)C52—C53—C58—C57177.2 (3)
Symmetry code: (i) x+1, y+1, z+2.
catena-Poly[[[(1,3-dibenzyl-4,5-diphenyl-2-selenoimidazole-κSe)copper(I)]-µ-cyanido-κ2C:N] acetonitrile monosolvate] (3) top
Crystal data top
[Cu(CN)(C29H24N2Se)]·C2H3NF(000) = 2480
Mr = 610.07Dx = 1.447 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7704 (3) ÅCell parameters from 23662 reflections
b = 14.3398 (3) Åθ = 3.0–26.3°
c = 28.4102 (7) ŵ = 2.11 mm1
β = 93.024 (2)°T = 100 K
V = 5602.2 (2) Å3Rod, colourless
Z = 80.35 × 0.12 × 0.11 mm
Data collection top
Rigaku SuperNova, Dual, Cu at zero, Atlas
diffractometer
11392 independent reflections
Radiation source: micro-focus sealed X-ray tube10122 reflections with I > 2σ(I)
Detector resolution: 10.3196 pixels mm-1Rint = 0.038
ω scansθmax = 26.4°, θmin = 2.8°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
h = 1717
Tmin = 0.643, Tmax = 0.851k = 1717
71725 measured reflectionsl = 3435
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.045P)2 + 17.9881P]
where P = (Fo2 + 2Fc2)/3
11392 reflections(Δ/σ)max = 0.002
687 parametersΔρmax = 2.04 e Å3
0 restraintsΔρmin = 0.56 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
C10.7661 (3)0.8105 (3)0.56492 (13)0.0266 (8)
H10.81510.79090.54480.032*
C20.6869 (3)0.8612 (3)0.54673 (14)0.0324 (9)
H20.68190.87580.51410.039*
C30.6153 (3)0.8906 (3)0.57562 (15)0.0332 (9)
H30.56200.92650.56310.040*
C40.6218 (3)0.8673 (3)0.62283 (15)0.0343 (9)
H40.57200.88590.64270.041*
C50.7008 (3)0.8171 (3)0.64125 (13)0.0253 (7)
H50.70510.80190.67380.030*
C60.7738 (2)0.7886 (2)0.61249 (12)0.0189 (7)
C70.8551 (2)0.7292 (2)0.63438 (12)0.0204 (7)
H7A0.87270.75320.66640.024*
H7B0.83100.66460.63770.024*
N10.9424 (2)0.72729 (19)0.60732 (9)0.0183 (6)
C80.9750 (2)0.6511 (2)0.58509 (11)0.0200 (7)
C91.0034 (2)0.8028 (2)0.60041 (11)0.0174 (6)
C100.9878 (2)0.8956 (2)0.62140 (11)0.0177 (6)
C110.9911 (2)0.9067 (2)0.67034 (12)0.0218 (7)
H111.00390.85450.69030.026*
C120.9757 (3)0.9937 (3)0.68992 (13)0.0262 (8)
H120.97731.00070.72320.031*
C130.9580 (3)1.0703 (3)0.66121 (14)0.0281 (8)
H130.94761.12980.67470.034*
C140.9554 (3)1.0602 (3)0.61274 (14)0.0284 (8)
H140.94381.11300.59300.034*
C150.9697 (3)0.9730 (2)0.59275 (12)0.0237 (7)
H150.96710.96630.55940.028*
C161.0749 (2)0.7722 (2)0.57321 (11)0.0188 (7)
C171.1600 (2)0.8218 (2)0.55600 (11)0.0180 (6)
C181.1500 (3)0.8798 (3)0.51648 (13)0.0301 (8)
H181.08830.88670.50030.036*
C191.2298 (3)0.9274 (3)0.50083 (15)0.0357 (9)
H191.22270.96670.47390.043*
C201.3199 (3)0.9176 (3)0.52444 (14)0.0313 (8)
H201.37430.95080.51390.038*
C211.3312 (3)0.8598 (3)0.56325 (13)0.0281 (8)
H211.39330.85250.57900.034*
C221.2508 (3)0.8122 (3)0.57926 (12)0.0235 (7)
H221.25820.77300.60620.028*
N21.0562 (2)0.67822 (19)0.56411 (9)0.0195 (6)
C231.1121 (3)0.6179 (2)0.53376 (12)0.0224 (7)
H23A1.14950.65760.51270.027*
H23B1.06630.58000.51370.027*
C241.1821 (3)0.5528 (3)0.56083 (13)0.0253 (7)
C251.2045 (3)0.5611 (3)0.60863 (13)0.0269 (8)
H251.17800.61110.62570.032*
C261.2657 (3)0.4965 (3)0.63204 (15)0.0384 (10)
H261.28120.50330.66480.046*
C271.3040 (3)0.4226 (4)0.60772 (16)0.0453 (11)
H271.34350.37740.62390.054*
C281.2840 (3)0.4152 (3)0.55930 (16)0.0464 (11)
H281.31210.36610.54210.056*
C291.2230 (3)0.4793 (3)0.53623 (15)0.0390 (10)
H291.20890.47330.50330.047*
Se10.92117 (3)0.53117 (2)0.58409 (2)0.02398 (10)
Cu10.95522 (3)0.49927 (3)0.66587 (2)0.02577 (11)
C590.9042 (3)0.3973 (3)0.69925 (13)0.0282 (8)
N50.8749 (2)0.3390 (2)0.72193 (12)0.0322 (7)
Cu20.82825 (3)0.24571 (3)0.76454 (2)0.02719 (12)
Se20.66152 (3)0.27327 (3)0.77892 (2)0.02914 (10)
C300.5614 (4)0.3668 (4)0.59119 (16)0.0474 (11)
H300.50370.40330.59050.057*
C310.6036 (5)0.3434 (5)0.54929 (18)0.0644 (16)
H310.57580.36490.52000.077*
C320.6879 (4)0.2878 (4)0.55079 (18)0.0641 (17)
H320.71360.26590.52240.077*
C330.7316 (5)0.2661 (5)0.5926 (2)0.084 (2)
H330.79240.23470.59370.101*
C340.6894 (4)0.2887 (4)0.63443 (18)0.0614 (16)
H340.72050.27060.66360.074*
C350.6040 (3)0.3366 (3)0.63423 (13)0.0280 (8)
C360.5573 (3)0.3625 (3)0.67936 (13)0.0262 (8)
H36A0.49600.39650.67140.031*
H36B0.54040.30470.69610.031*
N30.6190 (2)0.4204 (2)0.71106 (10)0.0216 (6)
C370.6612 (3)0.3937 (2)0.75286 (12)0.0232 (7)
C380.6364 (2)0.5153 (2)0.70361 (12)0.0199 (7)
C390.6004 (2)0.5646 (2)0.66026 (12)0.0208 (7)
C400.6554 (3)0.5642 (3)0.62088 (13)0.0283 (8)
H400.71640.53300.62190.034*
C410.6218 (3)0.6090 (3)0.57994 (14)0.0364 (10)
H410.66000.60910.55310.044*
C420.5336 (3)0.6530 (3)0.57830 (15)0.0427 (11)
H420.51040.68350.55020.051*
C430.4786 (3)0.6529 (4)0.61719 (19)0.0559 (14)
H430.41700.68310.61570.067*
C440.5114 (3)0.6097 (3)0.65840 (16)0.0430 (11)
H440.47320.61090.68530.052*
C450.6898 (2)0.5460 (2)0.74189 (12)0.0194 (7)
C460.7299 (2)0.6395 (2)0.75337 (11)0.0194 (7)
C470.8295 (3)0.6547 (2)0.75481 (12)0.0233 (7)
H470.87230.60510.74800.028*
C480.8669 (3)0.7425 (3)0.76618 (12)0.0276 (8)
H480.93520.75250.76730.033*
C490.8050 (3)0.8150 (3)0.77590 (13)0.0313 (9)
H490.83050.87500.78360.038*
C500.7054 (3)0.7999 (3)0.77436 (13)0.0314 (8)
H500.66290.84970.78110.038*
C510.6676 (3)0.7132 (3)0.76306 (12)0.0251 (7)
H510.59930.70350.76190.030*
N40.7045 (2)0.4698 (2)0.77188 (10)0.0214 (6)
C520.7539 (3)0.4747 (2)0.81887 (12)0.0235 (7)
H52A0.82090.49840.81590.028*
H52B0.75860.41120.83250.028*
C530.7010 (3)0.5374 (2)0.85174 (12)0.0223 (7)
C540.5996 (3)0.5417 (3)0.84997 (13)0.0292 (8)
H540.56270.50490.82770.035*
C550.5525 (3)0.5998 (3)0.88072 (15)0.0381 (10)
H550.48350.60280.87930.046*
C560.6058 (3)0.6533 (3)0.91339 (16)0.0426 (10)
H560.57360.69320.93420.051*
C570.7057 (3)0.6483 (3)0.91558 (15)0.0411 (10)
H570.74240.68460.93810.049*
C580.7534 (3)0.5903 (3)0.88486 (13)0.0302 (8)
H580.82240.58710.88670.036*
C600.9083 (3)0.1490 (2)0.79035 (12)0.0238 (7)
N60.9596 (2)0.0943 (2)0.80625 (11)0.0280 (7)
N70.5766 (3)0.4987 (3)0.24282 (14)0.0445 (9)
C610.6400 (3)0.4766 (3)0.22229 (16)0.0365 (9)
C620.7238 (4)0.4507 (4)0.1964 (2)0.0624 (16)
H62A0.70240.41550.16820.094*
H62B0.76770.41210.21640.094*
H62C0.75810.50720.18710.094*
N80.9405 (3)0.7629 (3)0.47523 (14)0.0484 (10)
C630.9333 (3)0.7302 (3)0.43914 (15)0.0340 (9)
C640.9265 (4)0.6919 (3)0.39148 (16)0.0476 (11)
H64A0.87530.72450.37270.071*
H64B0.91090.62530.39290.071*
H64C0.98880.70010.37690.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0223 (18)0.035 (2)0.0229 (18)0.0024 (15)0.0034 (14)0.0067 (15)
C20.030 (2)0.039 (2)0.028 (2)0.0039 (17)0.0033 (16)0.0129 (17)
C30.0228 (19)0.029 (2)0.047 (2)0.0033 (15)0.0051 (17)0.0048 (17)
C40.0237 (19)0.038 (2)0.041 (2)0.0055 (16)0.0071 (17)0.0092 (18)
C50.0246 (18)0.0293 (19)0.0222 (18)0.0007 (14)0.0043 (14)0.0037 (14)
C60.0183 (16)0.0174 (15)0.0212 (16)0.0028 (12)0.0018 (13)0.0007 (13)
C70.0200 (16)0.0244 (17)0.0173 (16)0.0015 (13)0.0062 (13)0.0041 (13)
N10.0178 (14)0.0198 (14)0.0172 (13)0.0013 (11)0.0015 (11)0.0004 (11)
C80.0218 (17)0.0209 (16)0.0170 (16)0.0032 (13)0.0014 (13)0.0002 (13)
C90.0169 (16)0.0216 (16)0.0135 (15)0.0027 (12)0.0005 (12)0.0018 (12)
C100.0155 (15)0.0195 (16)0.0184 (16)0.0019 (12)0.0037 (12)0.0004 (12)
C110.0187 (16)0.0263 (17)0.0204 (17)0.0001 (13)0.0004 (13)0.0008 (14)
C120.0219 (18)0.0318 (19)0.0251 (18)0.0009 (14)0.0047 (14)0.0084 (15)
C130.0225 (18)0.0231 (18)0.039 (2)0.0000 (14)0.0069 (16)0.0098 (16)
C140.0283 (19)0.0226 (18)0.035 (2)0.0040 (15)0.0062 (16)0.0042 (15)
C150.0266 (18)0.0240 (17)0.0207 (17)0.0031 (14)0.0040 (14)0.0003 (14)
C160.0223 (17)0.0209 (16)0.0131 (15)0.0050 (13)0.0019 (12)0.0016 (12)
C170.0193 (16)0.0207 (16)0.0144 (15)0.0036 (13)0.0035 (12)0.0014 (12)
C180.0244 (18)0.040 (2)0.0260 (19)0.0019 (16)0.0010 (15)0.0080 (16)
C190.032 (2)0.043 (2)0.033 (2)0.0007 (18)0.0044 (17)0.0143 (18)
C200.0261 (19)0.032 (2)0.037 (2)0.0038 (16)0.0085 (16)0.0020 (17)
C210.0207 (18)0.033 (2)0.031 (2)0.0021 (15)0.0011 (15)0.0050 (16)
C220.0243 (18)0.0279 (18)0.0185 (16)0.0024 (14)0.0021 (14)0.0005 (14)
N20.0196 (14)0.0224 (14)0.0165 (14)0.0035 (11)0.0022 (11)0.0019 (11)
C230.0254 (18)0.0247 (17)0.0172 (16)0.0039 (14)0.0035 (14)0.0032 (13)
C240.0227 (18)0.0296 (19)0.0235 (18)0.0052 (14)0.0008 (14)0.0017 (15)
C250.0266 (19)0.0305 (19)0.0237 (18)0.0027 (15)0.0015 (14)0.0045 (15)
C260.035 (2)0.053 (3)0.026 (2)0.0072 (19)0.0058 (17)0.0002 (18)
C270.038 (2)0.057 (3)0.040 (2)0.016 (2)0.0028 (19)0.009 (2)
C280.048 (3)0.050 (3)0.041 (2)0.025 (2)0.000 (2)0.004 (2)
C290.046 (2)0.044 (2)0.027 (2)0.017 (2)0.0013 (18)0.0035 (18)
Se10.02574 (19)0.02198 (18)0.02412 (19)0.00181 (13)0.00024 (14)0.00282 (13)
Cu10.0309 (2)0.0204 (2)0.0263 (2)0.00198 (17)0.00483 (18)0.00115 (17)
C590.036 (2)0.0238 (18)0.0250 (19)0.0014 (15)0.0041 (16)0.0006 (15)
N50.0349 (18)0.0259 (17)0.0360 (18)0.0016 (14)0.0032 (14)0.0023 (14)
Cu20.0365 (3)0.0186 (2)0.0263 (2)0.00050 (18)0.00004 (19)0.00181 (17)
Se20.0374 (2)0.02157 (18)0.0290 (2)0.00150 (15)0.00708 (16)0.00452 (14)
C300.043 (3)0.065 (3)0.035 (2)0.007 (2)0.001 (2)0.007 (2)
C310.072 (4)0.090 (4)0.031 (3)0.021 (3)0.002 (2)0.013 (3)
C320.066 (4)0.089 (4)0.039 (3)0.022 (3)0.024 (3)0.037 (3)
C330.076 (4)0.116 (6)0.060 (4)0.047 (4)0.015 (3)0.030 (4)
C340.065 (3)0.083 (4)0.036 (3)0.034 (3)0.002 (2)0.013 (3)
C350.033 (2)0.0274 (19)0.0243 (18)0.0089 (15)0.0049 (15)0.0091 (15)
C360.0266 (19)0.0271 (18)0.0253 (18)0.0062 (15)0.0028 (15)0.0051 (15)
N30.0247 (15)0.0220 (14)0.0185 (14)0.0006 (12)0.0041 (12)0.0025 (11)
C370.0268 (18)0.0210 (17)0.0224 (17)0.0010 (14)0.0070 (14)0.0007 (14)
C380.0188 (16)0.0213 (16)0.0202 (17)0.0006 (13)0.0056 (13)0.0002 (13)
C390.0215 (17)0.0225 (16)0.0181 (16)0.0036 (13)0.0009 (13)0.0023 (13)
C400.033 (2)0.0285 (19)0.0243 (18)0.0025 (15)0.0062 (15)0.0016 (15)
C410.054 (3)0.036 (2)0.0202 (19)0.0099 (19)0.0053 (18)0.0018 (16)
C420.052 (3)0.044 (2)0.030 (2)0.014 (2)0.018 (2)0.0143 (19)
C430.033 (2)0.069 (3)0.065 (3)0.012 (2)0.003 (2)0.035 (3)
C440.033 (2)0.057 (3)0.040 (2)0.015 (2)0.0140 (19)0.020 (2)
C450.0185 (16)0.0216 (16)0.0188 (16)0.0041 (13)0.0068 (13)0.0007 (13)
C460.0248 (17)0.0213 (16)0.0123 (15)0.0006 (13)0.0010 (13)0.0010 (12)
C470.0267 (18)0.0257 (18)0.0175 (16)0.0010 (14)0.0017 (14)0.0015 (13)
C480.030 (2)0.032 (2)0.0205 (17)0.0070 (16)0.0002 (15)0.0021 (15)
C490.049 (2)0.0245 (19)0.0204 (18)0.0069 (17)0.0023 (16)0.0005 (14)
C500.044 (2)0.0229 (18)0.0271 (19)0.0058 (16)0.0042 (17)0.0024 (15)
C510.0247 (18)0.0271 (18)0.0235 (18)0.0025 (14)0.0032 (14)0.0005 (14)
N40.0261 (15)0.0209 (14)0.0174 (14)0.0020 (12)0.0027 (11)0.0013 (11)
C520.0244 (18)0.0251 (17)0.0209 (17)0.0003 (14)0.0015 (14)0.0051 (14)
C530.0267 (18)0.0249 (17)0.0155 (16)0.0027 (14)0.0035 (13)0.0037 (13)
C540.0261 (19)0.036 (2)0.0251 (19)0.0069 (16)0.0014 (15)0.0022 (16)
C550.028 (2)0.054 (3)0.032 (2)0.0029 (19)0.0047 (17)0.0054 (19)
C560.048 (3)0.044 (2)0.038 (2)0.002 (2)0.014 (2)0.0121 (19)
C570.046 (3)0.046 (2)0.032 (2)0.018 (2)0.0035 (19)0.0149 (19)
C580.029 (2)0.036 (2)0.0264 (19)0.0104 (16)0.0034 (15)0.0013 (16)
C600.0297 (19)0.0225 (17)0.0195 (17)0.0037 (15)0.0045 (14)0.0009 (14)
N60.0349 (18)0.0267 (16)0.0229 (16)0.0004 (14)0.0078 (13)0.0035 (13)
N70.037 (2)0.047 (2)0.050 (2)0.0062 (17)0.0076 (18)0.0022 (18)
C610.031 (2)0.037 (2)0.042 (2)0.0038 (18)0.0033 (19)0.0119 (18)
C620.044 (3)0.064 (3)0.081 (4)0.023 (3)0.020 (3)0.030 (3)
N80.042 (2)0.072 (3)0.032 (2)0.003 (2)0.0019 (17)0.0028 (19)
C630.032 (2)0.036 (2)0.034 (2)0.0025 (17)0.0027 (17)0.0068 (18)
C640.064 (3)0.040 (2)0.038 (2)0.012 (2)0.003 (2)0.005 (2)
Geometric parameters (Å, º) top
C1—C61.386 (5)C30—H300.9500
C1—C21.388 (5)C31—C321.407 (9)
C1—H10.9500C31—H310.9500
C2—C31.382 (6)C32—C331.340 (9)
C2—H20.9500C32—H320.9500
C3—C41.381 (6)C33—C341.389 (7)
C3—H30.9500C33—H330.9500
C4—C51.384 (5)C34—C351.360 (6)
C4—H40.9500C34—H340.9500
C5—C61.391 (5)C35—C361.512 (5)
C5—H50.9500C36—N31.464 (4)
C6—C71.513 (5)C36—H36A0.9900
C7—N11.461 (4)C36—H36B0.9900
C7—H7A0.9900N3—C371.350 (5)
C7—H7B0.9900N3—C381.399 (4)
N1—C81.351 (4)C37—N41.343 (5)
N1—C91.391 (4)C38—C451.354 (5)
C8—N21.351 (4)C38—C391.483 (5)
C8—Se11.872 (3)C39—C401.383 (5)
C9—C161.356 (5)C39—C441.385 (5)
C9—C101.478 (4)C40—C411.387 (6)
C10—C151.391 (5)C40—H400.9500
C10—C111.398 (5)C41—C421.367 (7)
C11—C121.386 (5)C41—H410.9500
C11—H110.9500C42—C431.372 (7)
C12—C131.382 (5)C42—H420.9500
C12—H120.9500C43—C441.379 (6)
C13—C141.383 (5)C43—H430.9500
C13—H130.9500C44—H440.9500
C14—C151.391 (5)C45—N41.394 (4)
C14—H140.9500C45—C461.480 (5)
C15—H150.9500C46—C471.387 (5)
C16—N21.393 (4)C46—C511.397 (5)
C16—C171.478 (5)C47—C481.391 (5)
C17—C221.389 (5)C47—H470.9500
C17—C181.398 (5)C48—C491.382 (6)
C18—C191.386 (6)C48—H480.9500
C18—H180.9500C49—C501.386 (6)
C19—C201.386 (6)C49—H490.9500
C19—H190.9500C50—C511.380 (5)
C20—C211.382 (6)C50—H500.9500
C20—H200.9500C51—H510.9500
C21—C221.398 (5)N4—C521.468 (4)
C21—H210.9500C52—C531.512 (5)
C22—H220.9500C52—H52A0.9900
N2—C231.468 (4)C52—H52B0.9900
C23—C241.521 (5)C53—C581.382 (5)
C23—H23A0.9900C53—C541.395 (5)
C23—H23B0.9900C54—C551.392 (6)
C24—C251.382 (5)C54—H540.9500
C24—C291.399 (5)C55—C561.384 (6)
C25—C261.397 (6)C55—H550.9500
C25—H250.9500C56—C571.375 (6)
C26—C271.384 (6)C56—H560.9500
C26—H260.9500C57—C581.395 (6)
C27—C281.393 (6)C57—H570.9500
C27—H270.9500C58—H580.9500
C28—C291.386 (6)C60—N61.134 (5)
C28—H280.9500N6—Cu1ii1.939 (3)
C29—H290.9500N7—C611.121 (6)
Se1—Cu12.3900 (6)C61—C621.450 (7)
Cu1—C591.898 (4)C62—H62A0.9800
Cu1—N6i1.939 (3)C62—H62B0.9800
C59—N51.141 (5)C62—H62C0.9800
N5—Cu21.937 (3)N8—C631.127 (6)
Cu2—C601.895 (4)C63—C641.460 (6)
Cu2—Se22.3861 (6)C64—H64A0.9800
Se2—C371.879 (3)C64—H64B0.9800
C30—C311.393 (7)C64—H64C0.9800
C30—C351.397 (6)
C6—C1—C2120.0 (3)C30—C31—C32119.4 (5)
C6—C1—H1120.0C30—C31—H31120.3
C2—C1—H1120.0C32—C31—H31120.3
C3—C2—C1120.7 (4)C33—C32—C31119.3 (5)
C3—C2—H2119.7C33—C32—H32120.3
C1—C2—H2119.7C31—C32—H32120.3
C4—C3—C2119.4 (4)C32—C33—C34121.0 (6)
C4—C3—H3120.3C32—C33—H33119.5
C2—C3—H3120.3C34—C33—H33119.5
C3—C4—C5120.2 (4)C35—C34—C33121.0 (5)
C3—C4—H4119.9C35—C34—H34119.5
C5—C4—H4119.9C33—C34—H34119.5
C4—C5—C6120.6 (3)C34—C35—C30118.9 (4)
C4—C5—H5119.7C34—C35—C36121.8 (4)
C6—C5—H5119.7C30—C35—C36119.2 (4)
C1—C6—C5119.1 (3)N3—C36—C35113.7 (3)
C1—C6—C7123.1 (3)N3—C36—H36A108.8
C5—C6—C7117.8 (3)C35—C36—H36A108.8
N1—C7—C6113.9 (3)N3—C36—H36B108.8
N1—C7—H7A108.8C35—C36—H36B108.8
C6—C7—H7A108.8H36A—C36—H36B107.7
N1—C7—H7B108.8C37—N3—C38109.9 (3)
C6—C7—H7B108.8C37—N3—C36126.1 (3)
H7A—C7—H7B107.7C38—N3—C36123.8 (3)
C8—N1—C9110.2 (3)N4—C37—N3106.5 (3)
C8—N1—C7124.4 (3)N4—C37—Se2126.6 (3)
C9—N1—C7125.4 (3)N3—C37—Se2126.9 (3)
N2—C8—N1106.0 (3)C45—C38—N3106.6 (3)
N2—C8—Se1126.5 (2)C45—C38—C39130.9 (3)
N1—C8—Se1127.5 (3)N3—C38—C39122.5 (3)
C16—C9—N1106.8 (3)C40—C39—C44119.5 (3)
C16—C9—C10130.3 (3)C40—C39—C38119.8 (3)
N1—C9—C10122.9 (3)C44—C39—C38120.7 (3)
C15—C10—C11119.1 (3)C39—C40—C41120.2 (4)
C15—C10—C9120.5 (3)C39—C40—H40119.9
C11—C10—C9120.4 (3)C41—C40—H40119.9
C12—C11—C10120.3 (3)C42—C41—C40120.0 (4)
C12—C11—H11119.9C42—C41—H41120.0
C10—C11—H11119.9C40—C41—H41120.0
C13—C12—C11120.3 (3)C41—C42—C43120.0 (4)
C13—C12—H12119.9C41—C42—H42120.0
C11—C12—H12119.9C43—C42—H42120.0
C12—C13—C14119.9 (3)C42—C43—C44120.9 (4)
C12—C13—H13120.0C42—C43—H43119.6
C14—C13—H13120.0C44—C43—H43119.6
C13—C14—C15120.3 (3)C43—C44—C39119.5 (4)
C13—C14—H14119.9C43—C44—H44120.3
C15—C14—H14119.9C39—C44—H44120.3
C10—C15—C14120.2 (3)C38—C45—N4106.9 (3)
C10—C15—H15119.9C38—C45—C46130.8 (3)
C14—C15—H15119.9N4—C45—C46122.4 (3)
C9—C16—N2106.7 (3)C47—C46—C51119.4 (3)
C9—C16—C17130.1 (3)C47—C46—C45120.4 (3)
N2—C16—C17123.1 (3)C51—C46—C45120.1 (3)
C22—C17—C18119.3 (3)C46—C47—C48120.2 (3)
C22—C17—C16120.3 (3)C46—C47—H47119.9
C18—C17—C16120.4 (3)C48—C47—H47119.9
C19—C18—C17120.3 (3)C49—C48—C47120.2 (4)
C19—C18—H18119.9C49—C48—H48119.9
C17—C18—H18119.9C47—C48—H48119.9
C18—C19—C20119.9 (4)C48—C49—C50119.7 (4)
C18—C19—H19120.0C48—C49—H49120.2
C20—C19—H19120.0C50—C49—H49120.2
C21—C20—C19120.5 (4)C51—C50—C49120.6 (4)
C21—C20—H20119.8C51—C50—H50119.7
C19—C20—H20119.8C49—C50—H50119.7
C20—C21—C22119.7 (3)C50—C51—C46119.9 (3)
C20—C21—H21120.2C50—C51—H51120.0
C22—C21—H21120.2C46—C51—H51120.0
C17—C22—C21120.3 (3)C37—N4—C45110.1 (3)
C17—C22—H22119.8C37—N4—C52125.4 (3)
C21—C22—H22119.8C45—N4—C52124.3 (3)
C8—N2—C16110.2 (3)N4—C52—C53112.0 (3)
C8—N2—C23124.1 (3)N4—C52—H52A109.2
C16—N2—C23125.5 (3)C53—C52—H52A109.2
N2—C23—C24113.8 (3)N4—C52—H52B109.2
N2—C23—H23A108.8C53—C52—H52B109.2
C24—C23—H23A108.8H52A—C52—H52B107.9
N2—C23—H23B108.8C58—C53—C54119.1 (3)
C24—C23—H23B108.8C58—C53—C52119.7 (3)
H23A—C23—H23B107.7C54—C53—C52121.2 (3)
C25—C24—C29118.7 (3)C55—C54—C53120.2 (4)
C25—C24—C23123.1 (3)C55—C54—H54119.9
C29—C24—C23118.1 (3)C53—C54—H54119.9
C24—C25—C26120.6 (4)C56—C55—C54120.3 (4)
C24—C25—H25119.7C56—C55—H55119.9
C26—C25—H25119.7C54—C55—H55119.9
C27—C26—C25120.4 (4)C57—C56—C55119.7 (4)
C27—C26—H26119.8C57—C56—H56120.2
C25—C26—H26119.8C55—C56—H56120.2
C26—C27—C28119.4 (4)C56—C57—C58120.4 (4)
C26—C27—H27120.3C56—C57—H57119.8
C28—C27—H27120.3C58—C57—H57119.8
C29—C28—C27119.9 (4)C53—C58—C57120.4 (4)
C29—C28—H28120.0C53—C58—H58119.8
C27—C28—H28120.0C57—C58—H58119.8
C28—C29—C24120.9 (4)N6—C60—Cu2176.7 (3)
C28—C29—H29119.6C60—N6—Cu1ii178.6 (3)
C24—C29—H29119.6N7—C61—C62178.0 (5)
C8—Se1—Cu195.96 (10)C61—C62—H62A109.5
C59—Cu1—N6i124.68 (14)C61—C62—H62B109.5
C59—Cu1—Se1125.06 (12)H62A—C62—H62B109.5
N6i—Cu1—Se1110.25 (9)C61—C62—H62C109.5
N5—C59—Cu1175.6 (3)H62A—C62—H62C109.5
C59—N5—Cu2175.7 (3)H62B—C62—H62C109.5
C60—Cu2—N5122.84 (15)N8—C63—C64177.2 (5)
C60—Cu2—Se2126.88 (11)C63—C64—H64A109.5
N5—Cu2—Se2110.28 (10)C63—C64—H64B109.5
C37—Se2—Cu293.84 (11)H64A—C64—H64B109.5
C31—C30—C35119.8 (5)C63—C64—H64C109.5
C31—C30—H30120.1H64A—C64—H64C109.5
C35—C30—H30120.1H64B—C64—H64C109.5
C6—C1—C2—C30.3 (6)C35—C30—C31—C321.3 (8)
C1—C2—C3—C41.5 (6)C30—C31—C32—C336.6 (9)
C2—C3—C4—C51.7 (6)C31—C32—C33—C347.2 (11)
C3—C4—C5—C60.7 (6)C32—C33—C34—C352.3 (11)
C2—C1—C6—C50.8 (5)C33—C34—C35—C303.1 (9)
C2—C1—C6—C7176.6 (3)C33—C34—C35—C36179.5 (6)
C4—C5—C6—C10.5 (5)C31—C30—C35—C343.5 (7)
C4—C5—C6—C7176.6 (3)C31—C30—C35—C36180.0 (4)
C1—C6—C7—N122.7 (5)C34—C35—C36—N358.9 (6)
C5—C6—C7—N1161.4 (3)C30—C35—C36—N3117.5 (4)
C6—C7—N1—C8112.7 (3)C35—C36—N3—C37110.2 (4)
C6—C7—N1—C966.9 (4)C35—C36—N3—C3875.0 (4)
C9—N1—C8—N20.1 (4)C38—N3—C37—N40.2 (4)
C7—N1—C8—N2179.5 (3)C36—N3—C37—N4175.2 (3)
C9—N1—C8—Se1178.8 (2)C38—N3—C37—Se2178.8 (2)
C7—N1—C8—Se11.5 (5)C36—N3—C37—Se25.8 (5)
C8—N1—C9—C160.2 (4)Cu2—Se2—C37—N472.0 (3)
C7—N1—C9—C16179.5 (3)Cu2—Se2—C37—N3106.7 (3)
C8—N1—C9—C10178.5 (3)C37—N3—C38—C450.3 (4)
C7—N1—C9—C101.8 (5)C36—N3—C38—C45175.2 (3)
C16—C9—C10—C1563.8 (5)C37—N3—C38—C39179.0 (3)
N1—C9—C10—C15117.8 (4)C36—N3—C38—C395.5 (5)
C16—C9—C10—C11116.2 (4)C45—C38—C39—C4092.5 (5)
N1—C9—C10—C1162.2 (4)N3—C38—C39—C4086.6 (4)
C15—C10—C11—C120.5 (5)C45—C38—C39—C4488.8 (5)
C9—C10—C11—C12179.5 (3)N3—C38—C39—C4492.1 (5)
C10—C11—C12—C130.7 (5)C44—C39—C40—C410.4 (6)
C11—C12—C13—C140.1 (5)C38—C39—C40—C41179.1 (3)
C12—C13—C14—C150.6 (6)C39—C40—C41—C420.7 (6)
C11—C10—C15—C140.2 (5)C40—C41—C42—C430.2 (7)
C9—C10—C15—C14179.8 (3)C41—C42—C43—C440.6 (8)
C13—C14—C15—C100.7 (6)C42—C43—C44—C390.9 (8)
N1—C9—C16—N20.1 (3)C40—C39—C44—C430.4 (7)
C10—C9—C16—N2178.4 (3)C38—C39—C44—C43178.3 (4)
N1—C9—C16—C17178.4 (3)N3—C38—C45—N40.3 (4)
C10—C9—C16—C170.1 (6)C39—C38—C45—N4178.9 (3)
C9—C16—C17—C2298.5 (4)N3—C38—C45—C46179.5 (3)
N2—C16—C17—C2279.5 (4)C39—C38—C45—C460.3 (6)
C9—C16—C17—C1880.8 (5)C38—C45—C46—C47111.4 (4)
N2—C16—C17—C18101.2 (4)N4—C45—C46—C4767.7 (4)
C22—C17—C18—C190.2 (6)C38—C45—C46—C5168.9 (5)
C16—C17—C18—C19179.1 (4)N4—C45—C46—C51112.1 (4)
C17—C18—C19—C200.0 (6)C51—C46—C47—C480.5 (5)
C18—C19—C20—C210.7 (6)C45—C46—C47—C48179.2 (3)
C19—C20—C21—C221.1 (6)C46—C47—C48—C490.3 (5)
C18—C17—C22—C210.1 (5)C47—C48—C49—C500.1 (5)
C16—C17—C22—C21179.4 (3)C48—C49—C50—C510.2 (6)
C20—C21—C22—C170.8 (5)C49—C50—C51—C460.4 (6)
N1—C8—N2—C160.0 (4)C47—C46—C51—C500.6 (5)
Se1—C8—N2—C16178.9 (2)C45—C46—C51—C50179.1 (3)
N1—C8—N2—C23176.4 (3)N3—C37—N4—C450.0 (4)
Se1—C8—N2—C234.6 (5)Se2—C37—N4—C45178.9 (2)
C9—C16—N2—C80.0 (4)N3—C37—N4—C52175.7 (3)
C17—C16—N2—C8178.5 (3)Se2—C37—N4—C525.3 (5)
C9—C16—N2—C23176.4 (3)C38—C45—N4—C370.1 (4)
C17—C16—N2—C235.1 (5)C46—C45—N4—C37179.4 (3)
C8—N2—C23—C2481.7 (4)C38—C45—N4—C52175.9 (3)
C16—N2—C23—C24102.4 (4)C46—C45—N4—C524.8 (5)
N2—C23—C24—C2511.3 (5)C37—N4—C52—C53113.1 (4)
N2—C23—C24—C29166.4 (4)C45—N4—C52—C5362.0 (4)
C29—C24—C25—C260.9 (6)N4—C52—C53—C58145.1 (3)
C23—C24—C25—C26176.9 (4)N4—C52—C53—C5436.2 (5)
C24—C25—C26—C270.8 (7)C58—C53—C54—C551.1 (6)
C25—C26—C27—C282.5 (7)C52—C53—C54—C55179.8 (4)
C26—C27—C28—C292.6 (8)C53—C54—C55—C560.3 (6)
C27—C28—C29—C241.0 (8)C54—C55—C56—C570.4 (7)
C25—C24—C29—C280.8 (7)C55—C56—C57—C580.5 (7)
C23—C24—C29—C28177.1 (4)C54—C53—C58—C571.0 (6)
N2—C8—Se1—Cu1111.9 (3)C52—C53—C58—C57179.8 (4)
N1—C8—Se1—Cu166.9 (3)C56—C57—C58—C530.3 (7)
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+2, y1/2, z+3/2.
Selected internuclear distances and bond angles (Å, °) for (1), (2) and (3) top
AtomsDistanceAtomsAngle
(1)
Ag1—C82.091 (2)S1—Ag3—S2127.68 (2)
Ag1—C372.085 (2)S2—Ag3—S3103.96 (2)
Ag2—C662.097 (2)S3—Ag3—S1126.94 (2)
Ag2—C952.102 (2)Sum358.58
Ag3—S12.4657 (5)C8—Ag1—C37173.06 (8)
Ag3—S22.5377 (6)C66—Ag2—C95172.01 (7)
Ag3—S32.4940 (6)Ag3—S —C117100.90 (7)
Ag3—S2—C11893.45 (8)
Ag3···N34.161 (2)Ag3—S3—C119105.56 (9)
Ag3···C663.069 (2)S1—C117—N9177.8 (2)
S2—C118—N10179.4 (3)
S3—C119—N11177.1 (2)
(2)
Ag—Se12.6899 (4)Br—Ag—Se1102.274 (13)
Ag—Se22.7677 (4)Br—Ag—Se2109.628 (12)
Ag—Se2#12.7187 (4)Br—Ag—Se2#1126.883 (14)
Ag—Br2.6631 (4)Se1—Ag—Se2110.623 (12)
Se1—Ag—Se2#1100.026 (11)
Se2—Ag—Se2#1106.352 (11)
Ag—Se1—C894.72 (8)
Ag—Se2—C37100.72 (8)
Ag#1—Se2—C37108.43 (8)
Ag—Se2—Ag#173.649 (11)
(3)
Cu1—Se12.3900 (6)Se1—Cu1—C59125.06 (12)
Cu1—C591.898 (4)Se1—Cu1—N6#2110.25 (9)
Cu1—N6#21.939 (3)C59—Cu1—N6#2124.68 (14)
Sum359.99
Cu2—Se22.3861 (6)Se2—Cu2—C60126.88 (11)
Cu2—C601.895 (4)Se2—Cu2—N5110.28 (10)
Cu2—N51.937 (3)C60—Cu2—N5122.84 (15)
Sum360.00
Cu1—Se1—C895.96 (10)
Cu2—Se2—C3793.84 (11)
Symmetry codes: (#1) -x+1, -y+1, -z+2; (#2) -x+2, y+1/2, -z+3/2.
 

Acknowledgements

The authors thank University College Dublin for financial support. DM is grateful for an Erasmus exchange financed by the European Union and HA for an MSc studentship from Saudi Arabia.

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