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Crystal structure of bis­­[1,3-bis­­(2,6-diiso­propyl­phen­yl)imidazol-2-yl­­idene]silver(I) chloride tetra­hydro­furan monosolvate

aInstitut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 April 2015; accepted 16 April 2015; online 22 April 2015)

In the title salt, [Ag(C27H36N2)2]Cl·C4H8O, the AgI atom is coordinated by two 1,3-bis­(2,6-di­methyl­phen­yl)imidazol-2-yl­idene ligands. The imidazole rings are inclined to one another by 46.69 (13)° and the benzene rings in each ligand are almost normal to the imdazole ring to which they are attached, with dihedral angles varying from 82.39 (13) to 88.27 (12)°. There are C—H⋯π inter­actions present in the cation, involving the two ligands, and the solvent mol­ecule is linked to the cation via a C—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by trifurcated C—H⋯(Cl,Cl,Cl) hydrogen bonds, forming slabs parallel to (101). One isopropyl group is disordered over two sets of sites with an occupancy ratio of 0.447 (17):0.553 (17) and the THF mol­ecule is disordered over two positions with an occupancy ratio of 0.589 (6):0.411 (6).

1. Chemical context

In the past few decades the reactivity of white phospho­rus towards nucleophilic agents has been studied extensively (Scheer et al., 2010[Scheer, M., Balázs, G. & Seitz, A. (2010). Chem. Rev. 110, 4236-4256.]). Previously, we have reported that the products of the reaction between P4 and the tri-tert-butyl­silanides (supersilanides) M[Si(tBu)3] (M = Li, Na, K) (Lerner, 2005[Lerner, H.-W. (2005). Coord. Chem. Rev. 249, 781-798.]) depend strongly on the stoichiometry and solvent (Lorbach et al., 2009[Lorbach, A., Nadj, A., Tüllmann, S., Dornhaus, F., Schödel, F., Sänger, I., Margraf, G., Bats, J. W., Bolte, M., Holthausen, M. C., Wagner, M. & Lerner, H.-W. (2009). Inorg. Chem. 48, 1005-1017.], 2011[Lorbach, A., Breitung, S., Sänger, I., Schödel, F., Bolte, M., Wagner, M. & Lerner, H.-W. (2011). Inorg. Chim. Acta, 378, 1-9.]). The sodium penta­phosphide Na2[P5(SitBu3)3] was directly accessible by treating P4 with four equivalents of the sodium silanide Na(thf)2[SitBu3] in benzene (Lerner et al., 2005[Lerner, H.-W., Margraf, G., Kaufmann, L., Bats, J. W., Bolte, M. & Wagner, M. (2005). Eur. J. Inorg. Chem. pp. 1932-1939.]).

[Scheme 1]

Recently, we have shown that the penta­phosphenide Na2[P5(SitBu3)3] can be converted into Ag2[P5(SitBu3)3] by a metathesis reaction between Na2[P5(SitBu3)3] and AgOCN (Lerner et al., 2005[Lerner, H.-W., Margraf, G., Kaufmann, L., Bats, J. W., Bolte, M. & Wagner, M. (2005). Eur. J. Inorg. Chem. pp. 1932-1939.]). In this paper we present the reaction of Na2[P5(SitBu3)3] with 1,3-bis­(2,6-diiso­propyl­phen­yl)imidazol-2-yliden)silver(I) chloride ([Ag(NHC)Cl]) in a molar ratio of 1:4 in THF which gives Ag2[P5(SitBu3)3] and [Ag(NHC)2]Cl. Herein, the crystal structure of one of the two products of this reaction, [Ag(NHC)2]Cl·THF, (I)[link], is described.

2. Structural commentary

The title compound (Fig. 1[link]) crystallizes with discrete bis­(1,3-bis­(2,6-di-iso­propyl­phen­yl)-2,3-di­hydro-1H-imidazol-2-ylidene)silver(I) cations, chloride anions and a THF solvent mol­ecule in a 1:1:1 ratio. The Ag atom is bonded to two C atoms with bond lengths Ag1—C4 = 2.103 (2) and Ag1—C1 = 2.1058 (19) Å. The C1—Ag1—C4 bond angle is almost perfectly linear at 179.36 (7)°. The dihedral angle between the two heterocycles is 46.70 (11)°. The two 2,6-di-iso­propyl­phenyl rings (C11–C16 and C21–C26) are inclined to the imdazole ring (N1/N2/C1–C3) by 86.64 (12) and 88.27 (12)°, respectively. In the second ligand, the two 2,6-di-iso­propyl­phenl rings (C31–C36 and C41–C46) are inclined to the imidazole ring (N3/N4/C4–C6) by 82.39 (13) and 83.41 (13)°, respectively. There are also C—H⋯π inter­actions present involving the two ligands (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of rings C31–C26, C11–C16 and C21–C26, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O71 0.95 2.42 3.292 (5) 153
C3—H3⋯Cl1 0.95 2.51 3.422 (2) 161
C35—H35⋯Cl1i 0.95 2.68 3.627 (3) 174
C43—H43⋯Cl1ii 0.95 2.64 3.562 (2) 163
C171—H17BCg1 0.98 2.81 3.532 (4) 131
C372—H37CCg2 0.98 2.94 3.613 (4) 126
C481—H48ACg3 0.98 2.98 3.840 (12) 147
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x+1, y, z.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound (I)[link], with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms and the minor occupied sites of the disordered isopropyl group and the disordered THF mol­ecule have been omitted for clarity.

3. Supra­molecular features

In the crystal, mol­ecules are bridged by the Cl anions which form C—H⋯Cl⋯H—C hydrogen bonds, forming slabs lying parallel to (101); Table 1[link] and Fig. 2[link].

[Figure 2]
Figure 2
The crystal packing of the title compound (I)[link], viewed along the b axis. The C—H⋯Cl and C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1[link] for details). Disordered atoms and H atoms not involved in hydrogen bonding have been omitted for clarity (Ag silver ball, Cl green ball).

4. Database survey

The structures of the same cation but with different anions have been reported, viz. bis­[1,3-bis­(2,6-di-iso­propyl­phen­yl)-2,3-di­hydro-1H-imidazol-2-yl­idene]silver(I) tetra­chlorido­gallate(III) (Ia) (Tang et al., 2012[Tang, S., Monot, J., El-Hellani, A., Michelet, B., Guillot, R., Bour, C. & Gandon, V. (2012). Chem. Eur. J. 18, 10239-10243.]) and bis­[1,3-bis­(2,6-diiso­propyl­phen­yl)imidazol-2-yl­idene]silver hexa­fluorido­anti­mon­ate(V) (Ib) (Partyka & Deligonul, 2009[Partyka, D. V. & Deligonul, N. (2009). Inorg. Chem. 48, 9463-9475.]). These two structures have a bond angle of exactly 180° at the Ag atom due to symmetry whereas the C—Ag—C angle in the title compound deviates insignificantly from linearity [179.36 (7)°]. The Ag—C distances are also comparable with the values in the title compound [2.103 Å in (Ia) and 2.128 and 2.129 Å in (Ib)]. However, while the dihedral angle between the two heterocycles is 46.70 (11)° in the title compound, it is significantly smaller in (Ia) (32.4°) and (Ib) (37.8°).

A database search (CSD, Version 5.36, November 2014; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) for [1,3-bis­(2,6-diiso­propyl­phen­yl)imidazol-2-yl­idene]silver yielded eight hits with ten fragments. The mean Ag—C bond length in these structures is 2.09 (3) Å. These values agree well with those for the title compound, viz. Ag1—C1 = 2.1058 (19) and Ag1—C4 = 2.103 (2) Å.

5. Synthesis and crystallization

A solution of Na2[P5(SitBu3)3] (0.1 mmol) in 1 mL THF was treated with a solution of [Ag(NHC)Cl] (0.21 g, 0.4 mmol) 2 mL THF. The reaction mixture was stirred for 18 h at room temperature. After overlaying the THF solution with cyclo­hexane (6 mL), colourless block-like crystals of the title compound were obtained after 10 days at room temperature (yield: 41%).

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The C-bound H atoms were fixed geometrically and refined using a riding model approximation: C—H = 0.95–1.00 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. One isopropyl group (atoms C481/C482 and C483/C484) is disordered over two sets of sites with an occupancy ratio of 0.447 (17):0.553 (17) while the THF mol­ecule is disordered over two positions with an occupancy ratio of 0.589 (6):0.411 (6). Symmetry-equivalent bond lengths and angles in the two THF sites were restrained to be equal, distance C73′⋯C75′ was restrained to 2.30 (1) Å, and the displacement parameters of the C atoms were restrained to an isotropic behaviour.

Table 2
Experimental details

Crystal data
Chemical formula [Ag(C27H36N2)2]Cl·C4H8O
Mr 992.58
Crystal system, space group Monoclinic, P21/n
Temperature (K) 173
a, b, c (Å) 11.9302 (3), 18.3390 (5), 26.0144 (6)
β (°) 103.068 (2)
V3) 5544.2 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.45
Crystal size (mm) 0.31 × 0.27 × 0.26
 
Data collection
Diffractometer Stoe IPDS 2
Absorption correction Multi-scan (X-AREA; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.])
Tmin, Tmax 0.571, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 111561, 15949, 13800
Rint 0.075
(sin θ/λ)max−1) 0.705
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.121, 1.05
No. of reflections 15949
No. of parameters 651
No. of restraints 75
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.03, −1.37
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]), SHELXS97 and XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-RED32 (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Bis[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]silver(I) chloride tetrahydrofuran monosolvate top
Crystal data top
[Ag(C27H36N2)2]Cl·C4H8OF(000) = 2112
Mr = 992.58Dx = 1.189 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.9302 (3) ÅCell parameters from 115747 reflections
b = 18.3390 (5) Åθ = 2.0–30.3°
c = 26.0144 (6) ŵ = 0.45 mm1
β = 103.068 (2)°T = 173 K
V = 5544.2 (2) Å3Block, colourless
Z = 40.31 × 0.27 × 0.26 mm
Data collection top
Stoe IPDS 2
diffractometer
15949 independent reflections
Radiation source: fine-focus sealed tube13800 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.075
ω scansθmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 1616
Tmin = 0.571, Tmax = 1.000k = 2525
111561 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0596P)2 + 3.8737P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
15949 reflectionsΔρmax = 1.03 e Å3
651 parametersΔρmin = 1.37 e Å3
75 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.25283 (7)0.79025 (8)0.41564 (3)0.0832 (3)
Ag10.32700 (2)0.73977 (2)0.61445 (2)0.02859 (5)
N10.10444 (15)0.66141 (9)0.55242 (7)0.0324 (3)
N20.09066 (15)0.77562 (9)0.53662 (7)0.0318 (3)
C10.16299 (17)0.72485 (11)0.56468 (7)0.0295 (4)
C20.00005 (19)0.67258 (12)0.51718 (8)0.0366 (4)
H20.05490.63620.50280.044*
C30.00911 (19)0.74443 (12)0.50725 (9)0.0365 (4)
H30.07140.76890.48460.044*
C110.14323 (19)0.58950 (11)0.57077 (8)0.0339 (4)
C120.11632 (19)0.56315 (12)0.61711 (9)0.0376 (4)
C130.1487 (2)0.49169 (14)0.63150 (11)0.0472 (5)
H130.13420.47260.66330.057*
C140.2013 (3)0.44784 (14)0.60066 (12)0.0512 (6)
H140.22080.39890.61090.061*
C150.2255 (2)0.47539 (13)0.55510 (11)0.0472 (5)
H150.26130.44490.53400.057*
C160.1985 (2)0.54696 (12)0.53932 (9)0.0397 (5)
C170.0557 (2)0.61055 (14)0.65057 (9)0.0418 (5)
H170.00840.64720.62660.050*
C180.2273 (3)0.57670 (15)0.48954 (10)0.0484 (6)
H180.20440.62920.48620.058*
C210.11102 (17)0.85337 (11)0.53718 (8)0.0315 (4)
C220.16141 (18)0.88315 (12)0.49827 (8)0.0355 (4)
C230.1789 (2)0.95834 (13)0.49946 (10)0.0414 (5)
H230.21420.98020.47400.050*
C240.1459 (2)1.00192 (12)0.53687 (10)0.0421 (5)
H240.15951.05300.53720.051*
C250.0930 (2)0.97107 (12)0.57377 (9)0.0389 (4)
H250.06941.00150.59890.047*
C260.07386 (18)0.89620 (11)0.57481 (8)0.0342 (4)
C270.1978 (2)0.83601 (14)0.45695 (9)0.0421 (5)
H270.15540.78870.45520.050*
C280.0168 (2)0.86275 (13)0.61588 (9)0.0408 (5)
H280.00580.81160.60470.049*
N30.53162 (16)0.72843 (10)0.71425 (7)0.0346 (4)
N40.57794 (15)0.79569 (11)0.65566 (7)0.0350 (4)
C40.48997 (17)0.75476 (11)0.66489 (8)0.0292 (3)
C50.6422 (2)0.75307 (16)0.73539 (10)0.0474 (6)
H50.68840.74200.76930.057*
C60.6713 (2)0.79563 (16)0.69851 (10)0.0476 (6)
H60.74200.82080.70120.057*
C310.47404 (19)0.67686 (12)0.74141 (8)0.0346 (4)
C320.4827 (2)0.60301 (13)0.72966 (9)0.0421 (5)
C330.4296 (3)0.55367 (14)0.75715 (11)0.0501 (6)
H330.43200.50300.74980.060*
C340.3733 (2)0.57756 (15)0.79501 (10)0.0492 (6)
H340.33720.54310.81330.059*
C350.3688 (2)0.65110 (14)0.80671 (9)0.0444 (5)
H350.33120.66640.83340.053*
C360.4192 (2)0.70272 (12)0.77967 (8)0.0377 (4)
C370.5505 (3)0.57671 (16)0.69008 (12)0.0538 (6)
H370.57880.62080.67430.065*
C380.4136 (2)0.78324 (14)0.79234 (10)0.0451 (5)
H380.44060.81160.76460.054*
C410.58009 (17)0.83616 (12)0.60799 (8)0.0333 (4)
C420.61299 (18)0.79945 (13)0.56671 (9)0.0370 (4)
C430.6249 (2)0.84112 (15)0.52329 (9)0.0428 (5)
H430.64680.81820.49430.051*
C440.6050 (2)0.91521 (15)0.52225 (10)0.0477 (6)
H440.61500.94300.49280.057*
C450.5707 (2)0.94981 (14)0.56344 (10)0.0465 (5)
H450.55601.00080.56150.056*
C460.55756 (19)0.91082 (13)0.60776 (9)0.0389 (4)
C470.6370 (2)0.71821 (15)0.56861 (11)0.0470 (5)
H470.58840.69480.59060.056*
C480.5198 (2)0.94851 (15)0.65304 (11)0.0484 (5)
H480.50850.90870.67760.058*0.447 (17)
H48'0.55590.92190.68620.058*0.553 (17)
C1710.1420 (3)0.65204 (18)0.69207 (12)0.0595 (7)
H17A0.10090.68200.71300.089*
H17B0.19200.61740.71520.089*
H17C0.18880.68350.67480.089*
C1720.0252 (3)0.5682 (2)0.67752 (13)0.0685 (9)
H17D0.08120.54120.65090.103*
H17E0.01960.53380.70300.103*
H17F0.06580.60220.69590.103*
C1810.1623 (4)0.5374 (3)0.44116 (13)0.0885 (13)
H18A0.07950.54050.43950.133*
H18B0.17910.56000.40960.133*
H18C0.18580.48610.44290.133*
C2710.1680 (3)0.87042 (18)0.40178 (11)0.0579 (7)
H27A0.19310.83800.37660.087*
H27B0.08460.87780.39080.087*
H27C0.20720.91750.40260.087*
C2720.3262 (3)0.8194 (2)0.47309 (13)0.0701 (9)
H27D0.34830.78900.44610.105*
H27E0.36970.86520.47670.105*
H27F0.34300.79350.50690.105*
C2810.1018 (3)0.85940 (17)0.66940 (10)0.0547 (7)
H28A0.06400.83780.69550.082*
H28B0.16810.82950.66650.082*
H28C0.12780.90880.68060.082*
C3810.4926 (3)0.80103 (19)0.84580 (14)0.0658 (8)
H38A0.48750.85320.85310.099*
H38B0.46870.77270.87350.099*
H38C0.57210.78860.84510.099*
C3820.2906 (2)0.80671 (16)0.79172 (11)0.0521 (6)
H38D0.28950.85880.80000.078*
H38E0.24150.79770.75670.078*
H38F0.26180.77870.81810.078*
C4710.7617 (3)0.7022 (2)0.5937 (2)0.0959 (15)
H47A0.77460.64940.59440.144*
H47B0.81120.72570.57320.144*
H47C0.78030.72120.62990.144*
C4720.6065 (4)0.6833 (2)0.51324 (15)0.0744 (10)
H47D0.52570.69350.49670.112*
H47E0.65590.70390.49150.112*
H47F0.61840.63050.51640.112*
C2820.0920 (3)0.90368 (19)0.62077 (14)0.0614 (7)
H28D0.12550.88010.64760.092*
H28E0.07230.95430.63110.092*
H28F0.14780.90280.58670.092*
C3720.4758 (3)0.5337 (2)0.64546 (13)0.0747 (10)
H37A0.52220.51780.62090.112*
H37B0.44430.49090.65990.112*
H37C0.41260.56450.62670.112*
C3710.6557 (3)0.5331 (2)0.71798 (18)0.0836 (12)
H37D0.70190.56250.74650.125*
H37E0.63060.48840.73270.125*
H37F0.70210.52040.69260.125*
C1820.3550 (4)0.5721 (4)0.49240 (18)0.130 (3)
H18D0.39700.59780.52400.195*
H18E0.37880.52090.49420.195*
H18F0.37210.59480.46090.195*
C4810.4036 (10)0.9851 (11)0.6354 (4)0.082 (4)0.447 (17)
H48A0.34780.95010.61590.123*0.447 (17)
H48B0.37741.00230.66650.123*0.447 (17)
H48C0.41021.02670.61260.123*0.447 (17)
C4820.6139 (10)0.9942 (9)0.6833 (6)0.086 (5)0.447 (17)
H48D0.58841.01820.71230.130*0.447 (17)
H48E0.68100.96360.69760.130*0.447 (17)
H48F0.63481.03130.66000.130*0.447 (17)
C4830.3931 (7)0.9449 (6)0.6467 (4)0.070 (2)0.553 (17)
H48G0.37160.96960.67650.104*0.553 (17)
H48H0.35530.96890.61370.104*0.553 (17)
H48I0.36890.89370.64580.104*0.553 (17)
C4840.5609 (11)1.0302 (5)0.6600 (4)0.077 (3)0.553 (17)
H48J0.64461.03230.66420.116*0.553 (17)
H48K0.52341.05830.62880.116*0.553 (17)
H48L0.54031.05080.69140.116*0.553 (17)
O710.8401 (3)0.7674 (2)0.84592 (17)0.0709 (14)0.589 (6)
C720.9183 (7)0.7094 (4)0.8373 (3)0.081 (2)0.589 (6)
H72A0.96850.69410.87120.097*0.589 (6)
H72B0.87390.66650.82080.097*0.589 (6)
C730.9877 (7)0.7388 (4)0.8023 (3)0.0728 (18)0.589 (6)
H73A0.96380.71720.76660.087*0.589 (6)
H73B1.07030.72810.81640.087*0.589 (6)
C740.9636 (9)0.8317 (5)0.7999 (4)0.099 (3)0.589 (6)
H74A1.03090.86170.79690.119*0.589 (6)
H74B0.89270.84730.77450.119*0.589 (6)
C750.9500 (11)0.8200 (7)0.8552 (5)0.150 (5)0.589 (6)
H75A0.93530.86650.87180.180*0.589 (6)
H75B1.01870.79620.87730.180*0.589 (6)
O71'0.9421 (7)0.7754 (4)0.7663 (2)0.084 (2)0.411 (6)
C72'0.9671 (10)0.7119 (6)0.8015 (4)0.077 (3)0.411 (6)
H72C1.05030.70040.80870.092*0.411 (6)
H72D0.92400.66890.78440.092*0.411 (6)
C73'0.9325 (10)0.7283 (5)0.8529 (4)0.075 (3)0.411 (6)
H73C0.99660.71970.88380.090*0.411 (6)
H73D0.86450.69960.85650.090*0.411 (6)
C74'0.8976 (9)0.8296 (5)0.8429 (4)0.072 (2)0.411 (6)
H74C0.82480.84120.81740.087*0.411 (6)
H74D0.90840.85900.87560.087*0.411 (6)
C75'1.0046 (8)0.8220 (5)0.8193 (4)0.075 (3)0.411 (6)
H75C1.06720.79420.84260.089*0.411 (6)
H75D1.03400.86980.81050.089*0.411 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0488 (4)0.1689 (10)0.0337 (3)0.0122 (5)0.0133 (3)0.0032 (4)
Ag10.03022 (8)0.02622 (8)0.02919 (8)0.00159 (5)0.00643 (5)0.00055 (5)
N10.0379 (9)0.0265 (8)0.0320 (8)0.0028 (6)0.0063 (6)0.0009 (6)
N20.0345 (8)0.0266 (8)0.0328 (8)0.0026 (6)0.0046 (6)0.0013 (6)
C10.0306 (9)0.0266 (9)0.0300 (8)0.0016 (7)0.0041 (7)0.0001 (6)
C20.0363 (10)0.0338 (10)0.0372 (10)0.0064 (8)0.0028 (8)0.0032 (8)
C30.0333 (10)0.0365 (11)0.0366 (10)0.0042 (8)0.0016 (8)0.0008 (8)
C110.0384 (10)0.0244 (9)0.0386 (10)0.0052 (7)0.0081 (8)0.0022 (7)
C120.0384 (10)0.0343 (10)0.0405 (10)0.0044 (8)0.0100 (8)0.0016 (8)
C130.0560 (14)0.0375 (12)0.0501 (13)0.0036 (10)0.0163 (11)0.0092 (10)
C140.0618 (16)0.0290 (11)0.0637 (16)0.0017 (10)0.0164 (13)0.0068 (10)
C150.0563 (14)0.0310 (11)0.0577 (14)0.0002 (10)0.0197 (11)0.0060 (10)
C160.0479 (12)0.0307 (10)0.0426 (11)0.0047 (9)0.0144 (9)0.0052 (8)
C170.0444 (12)0.0458 (12)0.0371 (10)0.0009 (9)0.0132 (9)0.0009 (9)
C180.0662 (16)0.0420 (13)0.0424 (12)0.0014 (11)0.0235 (11)0.0041 (9)
C210.0321 (9)0.0260 (9)0.0334 (9)0.0017 (7)0.0008 (7)0.0028 (7)
C220.0343 (10)0.0331 (10)0.0381 (10)0.0016 (8)0.0060 (8)0.0034 (8)
C230.0421 (11)0.0356 (11)0.0458 (11)0.0059 (9)0.0081 (9)0.0085 (9)
C240.0455 (12)0.0280 (10)0.0489 (12)0.0042 (8)0.0021 (9)0.0050 (8)
C250.0441 (11)0.0307 (10)0.0390 (10)0.0008 (8)0.0032 (9)0.0013 (8)
C260.0372 (10)0.0304 (10)0.0327 (9)0.0011 (8)0.0031 (7)0.0014 (7)
C270.0436 (12)0.0428 (12)0.0419 (11)0.0011 (9)0.0139 (9)0.0036 (9)
C280.0519 (13)0.0335 (11)0.0389 (10)0.0019 (9)0.0138 (9)0.0003 (8)
N30.0350 (9)0.0377 (9)0.0317 (8)0.0020 (7)0.0089 (7)0.0065 (7)
N40.0310 (8)0.0413 (10)0.0330 (8)0.0016 (7)0.0078 (6)0.0075 (7)
C40.0287 (9)0.0314 (9)0.0281 (8)0.0006 (7)0.0079 (7)0.0020 (6)
C50.0362 (11)0.0635 (16)0.0386 (11)0.0074 (10)0.0001 (9)0.0128 (10)
C60.0309 (10)0.0644 (16)0.0444 (12)0.0091 (10)0.0019 (9)0.0142 (11)
C310.0385 (10)0.0357 (10)0.0294 (9)0.0011 (8)0.0077 (7)0.0077 (7)
C320.0485 (12)0.0365 (11)0.0424 (11)0.0036 (9)0.0123 (9)0.0036 (9)
C330.0643 (16)0.0338 (12)0.0525 (14)0.0004 (11)0.0137 (12)0.0091 (10)
C340.0592 (15)0.0440 (13)0.0452 (12)0.0054 (11)0.0138 (11)0.0157 (10)
C350.0532 (13)0.0489 (13)0.0339 (10)0.0022 (10)0.0154 (9)0.0079 (9)
C360.0458 (11)0.0383 (11)0.0296 (9)0.0004 (9)0.0096 (8)0.0042 (8)
C370.0631 (16)0.0443 (14)0.0586 (15)0.0085 (12)0.0236 (13)0.0011 (11)
C380.0557 (14)0.0392 (12)0.0428 (11)0.0013 (10)0.0160 (10)0.0016 (9)
C410.0292 (9)0.0373 (10)0.0342 (9)0.0045 (7)0.0088 (7)0.0069 (7)
C420.0312 (9)0.0414 (11)0.0407 (10)0.0050 (8)0.0131 (8)0.0021 (8)
C430.0371 (11)0.0554 (14)0.0385 (11)0.0078 (10)0.0138 (9)0.0034 (9)
C440.0463 (13)0.0549 (15)0.0415 (11)0.0114 (11)0.0088 (10)0.0160 (10)
C450.0477 (13)0.0385 (12)0.0495 (13)0.0048 (10)0.0029 (10)0.0106 (10)
C460.0367 (10)0.0390 (11)0.0396 (10)0.0034 (8)0.0054 (8)0.0016 (8)
C470.0448 (12)0.0410 (12)0.0613 (15)0.0012 (10)0.0246 (11)0.0009 (11)
C480.0494 (13)0.0467 (13)0.0474 (13)0.0018 (11)0.0075 (10)0.0053 (10)
C1710.0633 (17)0.0628 (18)0.0582 (16)0.0173 (14)0.0260 (13)0.0195 (13)
C1720.070 (2)0.081 (2)0.0649 (18)0.0287 (17)0.0377 (16)0.0225 (16)
C1810.112 (3)0.105 (3)0.0439 (16)0.030 (3)0.0069 (18)0.0029 (17)
C2710.0677 (18)0.0616 (17)0.0425 (13)0.0044 (14)0.0083 (12)0.0018 (12)
C2720.0559 (17)0.104 (3)0.0530 (16)0.0265 (17)0.0175 (13)0.0066 (16)
C2810.0689 (18)0.0589 (16)0.0372 (12)0.0109 (13)0.0135 (11)0.0050 (11)
C3810.0578 (17)0.0581 (18)0.074 (2)0.0042 (14)0.0018 (15)0.0213 (15)
C3820.0568 (15)0.0507 (14)0.0454 (13)0.0080 (12)0.0045 (11)0.0065 (11)
C4710.060 (2)0.067 (2)0.151 (4)0.0223 (18)0.003 (2)0.012 (3)
C4720.094 (3)0.0565 (19)0.082 (2)0.0096 (17)0.038 (2)0.0203 (16)
C2820.0504 (15)0.0671 (19)0.0712 (18)0.0040 (13)0.0228 (13)0.0133 (15)
C3720.081 (2)0.087 (3)0.0560 (17)0.018 (2)0.0150 (16)0.0169 (16)
C3710.060 (2)0.092 (3)0.097 (3)0.0220 (19)0.0157 (19)0.013 (2)
C1820.071 (3)0.252 (8)0.072 (3)0.036 (4)0.028 (2)0.043 (4)
C4810.065 (6)0.108 (11)0.072 (6)0.038 (7)0.013 (4)0.012 (6)
C4820.078 (6)0.094 (9)0.089 (8)0.017 (6)0.021 (5)0.052 (7)
C4830.055 (3)0.062 (5)0.094 (6)0.007 (3)0.024 (3)0.023 (4)
C4840.101 (7)0.056 (4)0.077 (5)0.022 (4)0.024 (5)0.023 (4)
O710.051 (2)0.092 (3)0.074 (3)0.0094 (19)0.0219 (18)0.027 (2)
C720.081 (2)0.081 (2)0.080 (2)0.0009 (10)0.0189 (11)0.0004 (10)
C730.072 (2)0.074 (2)0.073 (2)0.0001 (10)0.0175 (10)0.0006 (10)
C740.099 (3)0.099 (3)0.099 (3)0.0011 (10)0.0225 (11)0.0008 (10)
C750.151 (5)0.150 (5)0.150 (5)0.0003 (10)0.0333 (15)0.0001 (10)
O71'0.098 (5)0.090 (5)0.060 (4)0.000 (4)0.010 (3)0.005 (3)
C72'0.077 (3)0.077 (3)0.077 (3)0.0005 (10)0.0180 (12)0.0006 (10)
C73'0.075 (3)0.075 (3)0.074 (3)0.0009 (10)0.0174 (12)0.0001 (10)
C74'0.072 (3)0.073 (3)0.072 (3)0.0003 (10)0.0173 (11)0.0012 (10)
C75'0.074 (3)0.074 (3)0.076 (3)0.0002 (10)0.0178 (11)0.0001 (10)
Geometric parameters (Å, º) top
Ag1—C42.103 (2)C48—C4831.484 (8)
Ag1—C12.1058 (19)C48—C4811.516 (10)
N1—C11.357 (2)C48—C4841.574 (7)
N1—C21.385 (3)C48—H481.0000
N1—C111.443 (3)C48—H48'1.0000
N2—C11.364 (3)C171—H17A0.9800
N2—C31.384 (3)C171—H17B0.9800
N2—C211.446 (3)C171—H17C0.9800
C2—C31.342 (3)C172—H17D0.9800
C2—H20.9500C172—H17E0.9800
C3—H30.9500C172—H17F0.9800
C11—C161.399 (3)C181—H18A0.9800
C11—C121.402 (3)C181—H18B0.9800
C12—C131.393 (3)C181—H18C0.9800
C12—C171.524 (3)C271—H27A0.9800
C13—C141.383 (4)C271—H27B0.9800
C13—H130.9500C271—H27C0.9800
C14—C151.378 (4)C272—H27D0.9800
C14—H140.9500C272—H27E0.9800
C15—C161.391 (3)C272—H27F0.9800
C15—H150.9500C281—H28A0.9800
C16—C181.514 (3)C281—H28B0.9800
C17—C1711.517 (4)C281—H28C0.9800
C17—C1721.527 (4)C381—H38A0.9800
C17—H171.0000C381—H38B0.9800
C18—C1811.504 (4)C381—H38C0.9800
C18—C1821.511 (5)C382—H38D0.9800
C18—H181.0000C382—H38E0.9800
C21—C221.400 (3)C382—H38F0.9800
C21—C261.403 (3)C471—H47A0.9800
C22—C231.394 (3)C471—H47B0.9800
C22—C271.517 (3)C471—H47C0.9800
C23—C241.384 (4)C472—H47D0.9800
C23—H230.9500C472—H47E0.9800
C24—C251.383 (3)C472—H47F0.9800
C24—H240.9500C282—H28D0.9800
C25—C261.393 (3)C282—H28E0.9800
C25—H250.9500C282—H28F0.9800
C26—C281.520 (3)C372—H37A0.9800
C27—C2721.525 (4)C372—H37B0.9800
C27—C2711.534 (4)C372—H37C0.9800
C27—H271.0000C371—H37D0.9800
C28—C2811.527 (4)C371—H37E0.9800
C28—C2821.528 (4)C371—H37F0.9800
C28—H281.0000C182—H18D0.9800
N3—C41.356 (2)C182—H18E0.9800
N3—C51.386 (3)C182—H18F0.9800
N3—C311.444 (3)C481—H48A0.9800
N4—C41.355 (3)C481—H48B0.9800
N4—C61.387 (3)C481—H48C0.9800
N4—C411.451 (2)C482—H48D0.9800
C5—C61.342 (3)C482—H48E0.9800
C5—H50.9500C482—H48F0.9800
C6—H60.9500C483—H48G0.9800
C31—C361.392 (3)C483—H48H0.9800
C31—C321.397 (3)C483—H48I0.9800
C32—C331.392 (3)C484—H48J0.9800
C32—C371.525 (4)C484—H48K0.9800
C33—C341.383 (4)C484—H48L0.9800
C33—H330.9500O71—C721.465 (8)
C34—C351.386 (4)O71—C751.602 (11)
C34—H340.9500C72—C731.464 (9)
C35—C361.394 (3)C72—H72A0.9900
C35—H350.9500C72—H72B0.9900
C36—C381.518 (3)C73—C741.727 (11)
C37—C3721.515 (5)C73—H73A0.9900
C37—C3711.526 (5)C73—H73B0.9900
C37—H371.0000C74—C751.499 (11)
C38—C3821.526 (4)C74—H74A0.9900
C38—C3811.529 (4)C74—H74B0.9900
C38—H381.0000C75—H75A0.9900
C41—C461.395 (3)C75—H75B0.9900
C41—C421.397 (3)O71'—C72'1.472 (11)
C42—C431.397 (3)O71'—C75'1.651 (10)
C42—C471.516 (4)C72'—C73'1.515 (11)
C43—C441.378 (4)C72'—H72C0.9900
C43—H430.9500C72'—H72D0.9900
C44—C451.384 (4)C73'—C74'1.908 (12)
C44—H440.9500C73'—H73C0.9900
C45—C461.395 (3)C73'—H73D0.9900
C45—H450.9500C74'—C75'1.543 (11)
C46—C481.519 (3)C74'—H74C0.9900
C47—C4711.512 (4)C74'—H74D0.9900
C47—C4721.543 (4)C75'—H75C0.9900
C47—H471.0000C75'—H75D0.9900
C48—C4821.478 (9)
C4—Ag1—C1179.36 (7)C17—C171—H17B109.5
C1—N1—C2111.53 (17)H17A—C171—H17B109.5
C1—N1—C11126.59 (17)C17—C171—H17C109.5
C2—N1—C11121.83 (17)H17A—C171—H17C109.5
C1—N2—C3111.98 (17)H17B—C171—H17C109.5
C1—N2—C21125.69 (17)C17—C172—H17D109.5
C3—N2—C21122.31 (17)C17—C172—H17E109.5
N1—C1—N2103.28 (16)H17D—C172—H17E109.5
N1—C1—Ag1127.82 (14)C17—C172—H17F109.5
N2—C1—Ag1128.90 (14)H17D—C172—H17F109.5
C3—C2—N1107.07 (18)H17E—C172—H17F109.5
C3—C2—H2126.5C18—C181—H18A109.5
N1—C2—H2126.5C18—C181—H18B109.5
C2—C3—N2106.12 (19)H18A—C181—H18B109.5
C2—C3—H3126.9C18—C181—H18C109.5
N2—C3—H3126.9H18A—C181—H18C109.5
C16—C11—C12122.7 (2)H18B—C181—H18C109.5
C16—C11—N1118.33 (19)C27—C271—H27A109.5
C12—C11—N1118.76 (19)C27—C271—H27B109.5
C13—C12—C11116.9 (2)H27A—C271—H27B109.5
C13—C12—C17121.4 (2)C27—C271—H27C109.5
C11—C12—C17121.7 (2)H27A—C271—H27C109.5
C14—C13—C12121.7 (2)H27B—C271—H27C109.5
C14—C13—H13119.2C27—C272—H27D109.5
C12—C13—H13119.2C27—C272—H27E109.5
C15—C14—C13119.8 (2)H27D—C272—H27E109.5
C15—C14—H14120.1C27—C272—H27F109.5
C13—C14—H14120.1H27D—C272—H27F109.5
C14—C15—C16121.4 (2)H27E—C272—H27F109.5
C14—C15—H15119.3C28—C281—H28A109.5
C16—C15—H15119.3C28—C281—H28B109.5
C15—C16—C11117.5 (2)H28A—C281—H28B109.5
C15—C16—C18120.7 (2)C28—C281—H28C109.5
C11—C16—C18121.8 (2)H28A—C281—H28C109.5
C171—C17—C12111.0 (2)H28B—C281—H28C109.5
C171—C17—C172109.0 (2)C38—C381—H38A109.5
C12—C17—C172113.7 (2)C38—C381—H38B109.5
C171—C17—H17107.6H38A—C381—H38B109.5
C12—C17—H17107.6C38—C381—H38C109.5
C172—C17—H17107.6H38A—C381—H38C109.5
C181—C18—C182109.8 (3)H38B—C381—H38C109.5
C181—C18—C16111.7 (2)C38—C382—H38D109.5
C182—C18—C16111.0 (3)C38—C382—H38E109.5
C181—C18—H18108.1H38D—C382—H38E109.5
C182—C18—H18108.1C38—C382—H38F109.5
C16—C18—H18108.1H38D—C382—H38F109.5
C22—C21—C26122.77 (19)H38E—C382—H38F109.5
C22—C21—N2118.44 (19)C47—C471—H47A109.5
C26—C21—N2118.69 (18)C47—C471—H47B109.5
C23—C22—C21117.2 (2)H47A—C471—H47B109.5
C23—C22—C27120.9 (2)C47—C471—H47C109.5
C21—C22—C27121.88 (19)H47A—C471—H47C109.5
C24—C23—C22121.5 (2)H47B—C471—H47C109.5
C24—C23—H23119.3C47—C472—H47D109.5
C22—C23—H23119.3C47—C472—H47E109.5
C25—C24—C23119.9 (2)H47D—C472—H47E109.5
C25—C24—H24120.0C47—C472—H47F109.5
C23—C24—H24120.0H47D—C472—H47F109.5
C24—C25—C26121.3 (2)H47E—C472—H47F109.5
C24—C25—H25119.4C28—C282—H28D109.5
C26—C25—H25119.4C28—C282—H28E109.5
C25—C26—C21117.3 (2)H28D—C282—H28E109.5
C25—C26—C28120.9 (2)C28—C282—H28F109.5
C21—C26—C28121.81 (19)H28D—C282—H28F109.5
C22—C27—C272110.4 (2)H28E—C282—H28F109.5
C22—C27—C271112.7 (2)C37—C372—H37A109.5
C272—C27—C271110.2 (2)C37—C372—H37B109.5
C22—C27—H27107.8H37A—C372—H37B109.5
C272—C27—H27107.8C37—C372—H37C109.5
C271—C27—H27107.8H37A—C372—H37C109.5
C26—C28—C281110.2 (2)H37B—C372—H37C109.5
C26—C28—C282112.6 (2)C37—C371—H37D109.5
C281—C28—C282110.2 (2)C37—C371—H37E109.5
C26—C28—H28107.9H37D—C371—H37E109.5
C281—C28—H28107.9C37—C371—H37F109.5
C282—C28—H28107.9H37D—C371—H37F109.5
C4—N3—C5111.83 (18)H37E—C371—H37F109.5
C4—N3—C31125.68 (18)C18—C182—H18D109.5
C5—N3—C31122.35 (18)C18—C182—H18E109.5
C4—N4—C6111.76 (17)H18D—C182—H18E109.5
C4—N4—C41126.80 (17)C18—C182—H18F109.5
C6—N4—C41121.44 (18)H18D—C182—H18F109.5
N4—C4—N3103.43 (17)H18E—C182—H18F109.5
N4—C4—Ag1127.26 (14)C48—C481—H48A109.5
N3—C4—Ag1129.28 (14)C48—C481—H48B109.5
C6—C5—N3106.4 (2)H48A—C481—H48B109.5
C6—C5—H5126.8C48—C481—H48C109.5
N3—C5—H5126.8H48A—C481—H48C109.5
C5—C6—N4106.5 (2)H48B—C481—H48C109.5
C5—C6—H6126.7C48—C482—H48D109.5
N4—C6—H6126.7C48—C482—H48E109.5
C36—C31—C32123.8 (2)H48D—C482—H48E109.5
C36—C31—N3118.6 (2)C48—C482—H48F109.5
C32—C31—N3117.5 (2)H48D—C482—H48F109.5
C33—C32—C31116.9 (2)H48E—C482—H48F109.5
C33—C32—C37121.0 (2)C48—C483—H48G109.5
C31—C32—C37122.1 (2)C48—C483—H48H109.5
C34—C33—C32120.7 (2)H48G—C483—H48H109.5
C34—C33—H33119.6C48—C483—H48I109.5
C32—C33—H33119.6H48G—C483—H48I109.5
C33—C34—C35120.9 (2)H48H—C483—H48I109.5
C33—C34—H34119.6C48—C484—H48J109.5
C35—C34—H34119.6C48—C484—H48K109.5
C34—C35—C36120.5 (2)H48J—C484—H48K109.5
C34—C35—H35119.7C48—C484—H48L109.5
C36—C35—H35119.7H48J—C484—H48L109.5
C31—C36—C35117.1 (2)H48K—C484—H48L109.5
C31—C36—C38122.5 (2)C72—O71—C7586.1 (6)
C35—C36—C38120.4 (2)C73—C72—O71107.3 (6)
C372—C37—C32111.8 (3)C73—C72—H72A110.2
C372—C37—C371111.7 (3)O71—C72—H72A110.2
C32—C37—C371110.5 (3)C73—C72—H72B110.2
C372—C37—H37107.6O71—C72—H72B110.2
C32—C37—H37107.6H72A—C72—H72B108.5
C371—C37—H37107.5C72—C73—C74105.8 (6)
C36—C38—C382111.2 (2)C72—C73—H73A110.6
C36—C38—C381110.9 (2)C74—C73—H73A110.6
C382—C38—C381110.1 (2)C72—C73—H73B110.6
C36—C38—H38108.2C74—C73—H73B110.6
C382—C38—H38108.2H73A—C73—H73B108.7
C381—C38—H38108.2C75—C74—C7382.9 (7)
C46—C41—C42123.9 (2)C75—C74—H74A114.8
C46—C41—N4117.73 (19)C73—C74—H74A114.8
C42—C41—N4118.2 (2)C75—C74—H74B114.8
C41—C42—C43117.1 (2)C73—C74—H74B114.8
C41—C42—C47122.2 (2)H74A—C74—H74B111.9
C43—C42—C47120.7 (2)C74—C75—O71101.8 (8)
C44—C43—C42120.4 (2)C74—C75—H75A111.4
C44—C43—H43119.8O71—C75—H75A111.4
C42—C43—H43119.8C74—C75—H75B111.4
C43—C44—C45121.1 (2)O71—C75—H75B111.4
C43—C44—H44119.5H75A—C75—H75B109.3
C45—C44—H44119.5C72'—O71'—C75'84.2 (6)
C44—C45—C46120.9 (2)O71'—C72'—C73'109.5 (8)
C44—C45—H45119.6O71'—C72'—H72C109.8
C46—C45—H45119.6C73'—C72'—H72C109.8
C41—C46—C45116.7 (2)O71'—C72'—H72D109.8
C41—C46—C48122.3 (2)C73'—C72'—H72D109.8
C45—C46—C48121.1 (2)H72C—C72'—H72D108.2
C471—C47—C42111.4 (3)C72'—C73'—C74'99.8 (6)
C471—C47—C472109.0 (3)C72'—C73'—H73C111.8
C42—C47—C472112.0 (2)C74'—C73'—H73C111.8
C471—C47—H47108.1C72'—C73'—H73D111.8
C42—C47—H47108.1C74'—C73'—H73D111.8
C472—C47—H47108.1H73C—C73'—H73D109.5
C482—C48—C46110.4 (4)C75'—C74'—C73'77.9 (5)
C483—C48—C46111.5 (4)C75'—C74'—H74C115.6
C482—C48—C481116.3 (7)C73'—C74'—H74C115.6
C46—C48—C481112.3 (4)C75'—C74'—H74D115.6
C483—C48—C484109.8 (5)C73'—C74'—H74D115.6
C46—C48—C484112.5 (4)H74C—C74'—H74D112.6
C482—C48—H48105.7C74'—C75'—O71'97.0 (7)
C46—C48—H48105.7C74'—C75'—H75C112.4
C481—C48—H48105.7O71'—C75'—H75C112.4
C483—C48—H48'107.6C74'—C75'—H75D112.4
C46—C48—H48'107.6O71'—C75'—H75D112.4
C484—C48—H48'107.6H75C—C75'—H75D109.9
C17—C171—H17A109.5
C2—N1—C1—N21.0 (2)C31—N3—C4—Ag16.6 (3)
C11—N1—C1—N2178.67 (19)C4—N3—C5—C60.3 (3)
C2—N1—C1—Ag1178.36 (15)C31—N3—C5—C6175.7 (2)
C11—N1—C1—Ag10.6 (3)N3—C5—C6—N40.2 (3)
C3—N2—C1—N10.8 (2)C4—N4—C6—C50.7 (3)
C21—N2—C1—N1177.90 (19)C41—N4—C6—C5179.5 (2)
C3—N2—C1—Ag1178.49 (16)C4—N3—C31—C36101.7 (3)
C21—N2—C1—Ag12.8 (3)C5—N3—C31—C3682.9 (3)
C1—N1—C2—C30.8 (3)C4—N3—C31—C3281.9 (3)
C11—N1—C2—C3178.6 (2)C5—N3—C31—C3293.5 (3)
N1—C2—C3—N20.2 (3)C36—C31—C32—C332.1 (4)
C1—N2—C3—C20.4 (3)N3—C31—C32—C33178.2 (2)
C21—N2—C3—C2178.4 (2)C36—C31—C32—C37175.8 (2)
C1—N1—C11—C1693.8 (3)N3—C31—C32—C370.4 (3)
C2—N1—C11—C1683.7 (3)C31—C32—C33—C341.3 (4)
C1—N1—C11—C1291.0 (3)C37—C32—C33—C34176.6 (3)
C2—N1—C11—C1291.5 (2)C32—C33—C34—C350.3 (4)
C16—C11—C12—C130.8 (3)C33—C34—C35—C361.3 (4)
N1—C11—C12—C13175.8 (2)C32—C31—C36—C351.1 (3)
C16—C11—C12—C17179.8 (2)N3—C31—C36—C35177.3 (2)
N1—C11—C12—C174.8 (3)C32—C31—C36—C38178.6 (2)
C11—C12—C13—C142.1 (4)N3—C31—C36—C382.5 (3)
C17—C12—C13—C14178.5 (2)C34—C35—C36—C310.6 (4)
C12—C13—C14—C151.6 (4)C34—C35—C36—C38179.6 (2)
C13—C14—C15—C160.4 (4)C33—C32—C37—C37260.4 (4)
C14—C15—C16—C111.6 (4)C31—C32—C37—C372121.9 (3)
C14—C15—C16—C18179.1 (3)C33—C32—C37—C37164.6 (4)
C12—C11—C16—C151.0 (3)C31—C32—C37—C371113.1 (3)
N1—C11—C16—C15174.0 (2)C31—C36—C38—C382129.5 (2)
C12—C11—C16—C18179.7 (2)C35—C36—C38—C38250.7 (3)
N1—C11—C16—C185.3 (3)C31—C36—C38—C381107.6 (3)
C13—C12—C17—C17189.4 (3)C35—C36—C38—C38172.1 (3)
C11—C12—C17—C17190.0 (3)C4—N4—C41—C4698.9 (3)
C13—C12—C17—C17234.1 (3)C6—N4—C41—C4680.9 (3)
C11—C12—C17—C172146.6 (3)C4—N4—C41—C4285.9 (3)
C15—C16—C18—C18163.9 (4)C6—N4—C41—C4294.3 (3)
C11—C16—C18—C181115.4 (3)C46—C41—C42—C430.8 (3)
C15—C16—C18—C18259.0 (4)N4—C41—C42—C43174.10 (19)
C11—C16—C18—C182121.7 (4)C46—C41—C42—C47179.8 (2)
C1—N2—C21—C2294.2 (2)N4—C41—C42—C474.9 (3)
C3—N2—C21—C2287.2 (3)C41—C42—C43—C440.3 (3)
C1—N2—C21—C2689.2 (3)C47—C42—C43—C44178.7 (2)
C3—N2—C21—C2689.4 (2)C42—C43—C44—C451.3 (4)
C26—C21—C22—C232.9 (3)C43—C44—C45—C461.3 (4)
N2—C21—C22—C23179.34 (19)C42—C41—C46—C450.8 (3)
C26—C21—C22—C27178.2 (2)N4—C41—C46—C45174.13 (19)
N2—C21—C22—C271.7 (3)C42—C41—C46—C48178.9 (2)
C21—C22—C23—C241.2 (3)N4—C41—C46—C486.2 (3)
C27—C22—C23—C24179.9 (2)C44—C45—C46—C410.3 (3)
C22—C23—C24—C250.8 (4)C44—C45—C46—C48179.9 (2)
C23—C24—C25—C261.2 (4)C41—C42—C47—C47189.0 (3)
C24—C25—C26—C210.4 (3)C43—C42—C47—C47189.9 (3)
C24—C25—C26—C28179.4 (2)C41—C42—C47—C472148.6 (2)
C22—C21—C26—C252.5 (3)C43—C42—C47—C47232.4 (3)
N2—C21—C26—C25178.97 (18)C41—C46—C48—C482108.1 (9)
C22—C21—C26—C28178.5 (2)C45—C46—C48—C48272.3 (9)
N2—C21—C26—C282.1 (3)C41—C46—C48—C48386.4 (6)
C23—C22—C27—C27281.1 (3)C45—C46—C48—C48393.2 (6)
C21—C22—C27—C27297.8 (3)C41—C46—C48—C481120.4 (9)
C23—C22—C27—C27142.6 (3)C45—C46—C48—C48159.2 (9)
C21—C22—C27—C271138.5 (2)C41—C46—C48—C484149.7 (6)
C25—C26—C28—C28175.7 (3)C45—C46—C48—C48430.6 (6)
C21—C26—C28—C281103.2 (2)C75—O71—C72—C7345.6 (8)
C25—C26—C28—C28247.8 (3)O71—C72—C73—C7412.0 (9)
C21—C26—C28—C282133.3 (2)C72—C73—C74—C7531.5 (9)
C6—N4—C4—N30.8 (3)C73—C74—C75—O7163.1 (8)
C41—N4—C4—N3179.4 (2)C72—O71—C75—C7475.7 (9)
C6—N4—C4—Ag1177.48 (18)C75'—O71'—C72'—C73'46.5 (9)
C41—N4—C4—Ag12.3 (3)O71'—C72'—C73'—C74'8.2 (11)
C5—N3—C4—N40.7 (3)C73'—C74'—C75'—O71'70.7 (6)
C31—N3—C4—N4175.1 (2)C72'—O71'—C75'—C74'84.5 (7)
C5—N3—C4—Ag1177.59 (18)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of rings C31–C26, C11–C16 and C21–C26, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5···O710.952.423.292 (5)153
C3—H3···Cl10.952.513.422 (2)161
C35—H35···Cl1i0.952.683.627 (3)174
C43—H43···Cl1ii0.952.643.562 (2)163
C171—H17B···Cg10.982.813.532 (4)131
C372—H37C···Cg20.982.943.613 (4)126
C481—H48A···Cg30.982.983.840 (12)147
Symmetry codes: (i) x+1/2, y+3/2, z+1/2; (ii) x+1, y, z.
 

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