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Acta Cryst. (2007). E63, m2309-m2310    [ doi:10.1107/S1600536807037580 ]

Bis(1,10-phenanthroline-5,6-dione-[kappa]2N,N')silver(I) perchlorate

J. Onuegbu, R. J. Butcher, C. Hosten, U. C. Udeochu and O. Bakare

Abstract top

At 93 K, in the structure of a new polymorph of [AgL2]+(ClO4)- (L = 1,10-phenanthroline-5,6-dione) or [Ag(C12H6N2O2)2]ClO4, there is a complete formula unit in the asymmetric unit. The dihedral angle between the two phendione ligands is 36.7 (2)°. The geometry about the Ag atom is distorted tetrahedral. There are short contacts between the perchlorate anion and the phendione ligands [O...C = 2.845 (5) Å], as well as unusual and different O-C-C-O torsion angles for the two phendione ligands [-21.9 (7) and -5.0 (7)°], which reflects the fact that in this polymorph there is no crystallographically imposed symmetry in the cation.

Comment top

Phendione (1,10-phenanthroline-5,6-dione) is an excellent ligand that incorporates two functional groups with different coordination properties. Since the stereochemical behavior of Cu+ and Ag+ are similar it is interesting to compare the behavior of these cations with phendione. Isomorphous and isostructural Cu+ and Ag+ derivatives {[M(L)2](ClO4)2, where M = Cu+ and Ag+} have recently been determined (Galet et al., 2005; McCann et al., 2004) as well as a Ag+ complex, with trifluoromethanesulfonate instead of perchlorate as counterion (Wen et al., 2006). In addition a polymeric Ag+ phendione complex where the ligand coordinates to Ag through N and O donors has been reported (Wen et al., 2006). In this paper we report the synthesis and characterization of the title compound, [AgL2]+(ClO4)− (I).

The structure of the title compound, shown in Figure 1, is made up of an [Ag(L)2]+ cation and a perchlorate anion. Each silver atom is coordinated to the two nitrogen atoms of both phendione ligands. In contrast to the previous structure determination of this complex where there is crystallographically imposed symmetry on both the anion and cation in the present case there is no such symmetry. Table 1 gives a listing of selected bond lengths and bond angles. The C=O bond lengths in the phendione ligands (1.220 (5) Å and 1.207 (5) Å) are comparable to those values found in other such complexes (Allen, 2002). The metrical parameters for the phendione ligand is in the normal ranges observed for complexes where only the N atoms are coordinated to a metal (Allen, 2002). The Ag—N bond lengths (2.261 (3), 2.331 (4) Å, 2.349 (3) Å, and 2.453 (4) Å) are similar to those found in related phenanthroline derivatives of silver (McCann et al., 2004; Wen et al., 2006; Leschke et al., 2002; Paramonov et al., 2003; Pallenberg et al., 1997; Titze et al., 1997). In I, silver is in a distorted tetrahedral environment. This is best illustrated by the dihedral angle between the planes of the coordinated ligands which would be 90° for tetrahedral and 0° for planar. In this case the angle is 36.7 (2)° which is intermediate between these extremes.

There are weak C—H···O hydrogen bonds between the hydrogen atoms on C1A, C1B, C2A, C6A, C6B, C8A, and C8B and either perchlorate O atoms or phendione O atoms from an adjoining cation. In addition, there are short contacts between the perchlorate anion and the phendione ligands (O14···C4B 2.845 (5) Å) as well as unusual and different torsion angles for O1—C4—C5—O2 for the two phendione ligands (−21.9 (7)° and −5.0 (7)°) which reflects the fact that in this polymorph there is no crystallographically imposed symmetry on the cation.

Related literature top

For related literature, see: Galet et al. (2005); McCann et al. (2004); Pallenberg et al. (1997); Paramonov et al. (2003); Ruiz et al. (1999); Titze et al. (1997); Wen et al. (2006);

For related literature, see: Allen (2002); Leschke et al. (2002); Whitesides et al. (1991).

Experimental top

A flask containing 1,10-phenanthroline hydrate (1.00 g, 5.04 mmol) and potassium bromide (5.95 g, 50.0 mmol) was placed in an ice bath. Concentrated sulfuric acid (20 cm3) was added in small portions, followed by drop wise addition of concentrated nitric acid (10 cm3). The resulting solution was heated for 2 h at 80–85° C and cooled to room temperature. The solution was then poured into 400 cm3 of water and neutralized with sodium bicarbonate, after which the phendione was extracted with dichloromethane, and recrystallized using a methanol-water mixture.

The title compound was synthesized in an atmosphere saturated with N2. To a solution of AgClO4 in 15 ml of CH3CN, was added drop-wise a solution (15 ml) of CH3CN containing 0.26 g of phendione. The final yellowish solution was filtered and allowed to slowly evaporate for about a week yielding reddish brown prismatic crystals of the title compound suitable for X-ray studies.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound (I), [Ag(L)2]+(ClO4)−, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular packing of (I) viewed approximately along the c axis. Dotted lines indicate the hydrogen bonding interactions.
Bis(1,10-phenanthroline-5,6-dione-κ2N,N')silver(I) perchlorate top
Crystal data top
[Ag(C12H6N2O2)2]ClO4Z = 2
Mr = 627.70F000 = 624
Triclinic, P1Dx = 1.899 Mg m−3
a = 8.493 (2) ÅMo Kα radiation
λ = 0.71073 Å
b = 11.260 (3) ÅCell parameters from 6560 reflections
c = 13.190 (4) Åθ = 2.6–29.9º
α = 112.525 (3)ºµ = 1.10 mm−1
β = 103.682 (4)ºT = 93 (2) K
γ = 97.378 (4)ºPrism, red-brown
V = 1097.8 (5) Å30.38 × 0.32 × 0.12 mm
Data collection top
Bruker APEX II CCD area-detector
diffractometer		6019 independent reflections
Radiation source: fine-focus sealed tube4791 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.067
T = 273(2) Kθmax = 30.4º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→12
Tmin = 0.679, Tmax = 0.879k = −15→15
11431 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.184  w = 1/[σ2(Fo2) + (0.107P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6019 reflectionsΔρmax = 2.36 e Å−3
343 parametersΔρmin = −1.63 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag(C12H6N2O2)2]ClO4γ = 97.378 (4)º
Mr = 627.70V = 1097.8 (5) Å3
Triclinic, P1Z = 2
a = 8.493 (2) ÅMo Kα
b = 11.260 (3) ŵ = 1.10 mm−1
c = 13.190 (4) ÅT = 93 (2) K
α = 112.525 (3)º0.38 × 0.32 × 0.12 mm
β = 103.682 (4)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		6019 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4791 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.879Rint = 0.067
11431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066343 parameters
wR(F2) = 0.184H-atom parameters constrained
S = 1.07Δρmax = 2.36 e Å−3
6019 reflectionsΔρmin = −1.63 e Å−3
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*/Ueq
Ag0.13352 (4)0.50994 (3)0.25677 (2)0.02407 (14)
Cl−0.44552 (14)0.71466 (11)0.77901 (11)0.0285 (3)
O1A0.2299 (5)0.2746 (3)−0.2772 (3)0.0303 (7)
C9BB0.1294 (5)0.7156 (4)0.5018 (3)0.0169 (7)
N2B0.3438 (5)0.6887 (3)0.4071 (3)0.0193 (7)
N1B0.0294 (4)0.6065 (3)0.4095 (3)0.0197 (7)
C9AA0.1678 (5)0.4269 (4)0.0013 (3)0.0160 (7)
O14−0.6087 (4)0.7408 (3)0.7568 (3)0.0302 (7)
O2B0.4469 (5)1.0657 (3)0.7624 (3)0.0358 (8)
N2A0.0182 (4)0.3212 (3)0.0921 (3)0.0174 (6)
O1B0.1547 (5)0.9601 (3)0.7828 (3)0.0308 (7)
C8A−0.0858 (5)0.2175 (4)0.0876 (4)0.0215 (8)
H8AA−0.11220.22530.15410.026*
C1B−0.1214 (5)0.5583 (4)0.4135 (4)0.0232 (8)
H1BA−0.19160.48300.35000.028*
C5AA−0.0150 (5)0.1964 (4)−0.1072 (3)0.0176 (7)
C8BB0.2980 (5)0.7637 (4)0.4973 (3)0.0169 (7)
C6B0.5636 (5)0.9226 (4)0.5775 (3)0.0215 (8)
H6BA0.63641.00190.63410.026*
C3AA0.2244 (5)0.4194 (4)−0.0913 (3)0.0179 (7)
C7B0.6096 (5)0.8460 (4)0.4850 (4)0.0230 (8)
H7BA0.71380.87120.47810.028*
O2A−0.0645 (5)0.1084 (4)−0.3101 (3)0.0352 (8)
C4B0.1929 (6)0.9039 (4)0.6977 (4)0.0223 (8)
C3B−0.0743 (6)0.7283 (5)0.6016 (4)0.0248 (9)
H3BA−0.10840.76880.66590.030*
C6A−0.1213 (6)0.0888 (4)−0.1098 (4)0.0239 (8)
H6AA−0.16790.0112−0.17770.029*
N1A0.2144 (4)0.5387 (3)0.0994 (3)0.0199 (7)
C8AA0.0549 (5)0.3108 (4)−0.0038 (3)0.0166 (7)
C5A0.0205 (6)0.1890 (4)−0.2137 (4)0.0209 (8)
C4A0.1674 (6)0.2938 (4)−0.1997 (4)0.0226 (8)
C8B0.4943 (6)0.7290 (4)0.4016 (4)0.0229 (8)
H8BA0.52450.67650.33880.027*
C5BB0.4073 (5)0.8811 (4)0.5863 (3)0.0174 (7)
C3BB0.0804 (5)0.7798 (4)0.5979 (3)0.0196 (8)
C2A0.3813 (6)0.6438 (4)0.0180 (4)0.0243 (9)
H2AA0.45430.71860.02670.029*
C2B−0.1769 (6)0.6150 (4)0.5072 (4)0.0271 (9)
H2BA−0.28140.57780.50690.033*
C3A0.3321 (5)0.5288 (4)−0.0830 (4)0.0232 (8)
H3AA0.37040.5246−0.14440.028*
O13−0.3380 (5)0.7847 (4)0.7458 (4)0.0480 (11)
C7A−0.1556 (6)0.0998 (4)−0.0107 (4)0.0247 (9)
H7AA−0.22450.0293−0.00970.030*
C5B0.3604 (6)0.9603 (4)0.6878 (4)0.0220 (8)
C1A0.3188 (5)0.6445 (4)0.1060 (4)0.0201 (8)
H1AA0.35050.72240.17370.024*
O12−0.3734 (6)0.7661 (5)0.9063 (4)0.0550 (12)
O11−0.4590 (6)0.5775 (4)0.7348 (5)0.0566 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag0.0258 (2)0.01959 (18)0.01995 (18)0.00118 (13)0.00769 (12)0.00246 (13)
Cl0.0157 (5)0.0261 (5)0.0515 (7)0.0045 (4)0.0112 (4)0.0243 (5)
O1A0.0285 (18)0.0360 (18)0.0269 (15)0.0071 (15)0.0155 (13)0.0100 (14)
C9BB0.0136 (18)0.0170 (16)0.0230 (17)0.0055 (14)0.0091 (13)0.0090 (14)
N2B0.0152 (17)0.0213 (15)0.0199 (15)0.0058 (13)0.0082 (12)0.0053 (13)
N1B0.0159 (17)0.0212 (16)0.0218 (15)0.0051 (13)0.0059 (12)0.0089 (13)
C9AA0.0108 (17)0.0171 (16)0.0227 (17)0.0063 (13)0.0061 (13)0.0097 (14)
O140.0171 (16)0.0337 (17)0.0419 (18)0.0067 (14)0.0090 (13)0.0183 (15)
O2B0.044 (2)0.0232 (15)0.0261 (16)−0.0054 (15)0.0121 (14)0.0001 (13)
N2A0.0143 (16)0.0183 (15)0.0204 (15)0.0036 (13)0.0079 (12)0.0078 (13)
O1B0.041 (2)0.0267 (16)0.0269 (16)0.0122 (15)0.0188 (14)0.0082 (13)
C8A0.018 (2)0.0217 (18)0.0253 (19)0.0010 (15)0.0075 (14)0.0110 (16)
C1B0.0146 (19)0.027 (2)0.0265 (19)0.0001 (16)0.0046 (15)0.0126 (17)
C5AA0.0125 (18)0.0186 (16)0.0216 (17)0.0048 (14)0.0054 (13)0.0084 (14)
C8BB0.0135 (18)0.0170 (16)0.0200 (17)0.0054 (14)0.0059 (13)0.0071 (14)
C6B0.018 (2)0.0215 (18)0.0217 (18)−0.0018 (15)0.0029 (14)0.0101 (15)
C3AA0.0131 (18)0.0191 (17)0.0221 (17)0.0052 (14)0.0071 (13)0.0081 (15)
C7B0.0141 (19)0.027 (2)0.032 (2)0.0036 (16)0.0082 (15)0.0167 (18)
O2A0.0292 (19)0.0374 (18)0.0263 (16)−0.0060 (15)0.0049 (13)0.0072 (14)
C4B0.030 (2)0.0157 (16)0.0217 (18)0.0058 (16)0.0103 (15)0.0074 (15)
C3B0.022 (2)0.034 (2)0.029 (2)0.0143 (18)0.0161 (16)0.0173 (18)
C6A0.021 (2)0.0190 (17)0.028 (2)0.0041 (16)0.0067 (16)0.0072 (16)
N1A0.0147 (16)0.0157 (14)0.0283 (17)0.0022 (13)0.0067 (13)0.0088 (13)
C8AA0.0115 (17)0.0159 (16)0.0230 (17)0.0058 (14)0.0053 (13)0.0082 (14)
C5A0.020 (2)0.0210 (17)0.0225 (18)0.0056 (16)0.0096 (14)0.0079 (15)
C4A0.019 (2)0.0229 (18)0.0253 (19)0.0061 (16)0.0080 (15)0.0092 (16)
C8B0.019 (2)0.0259 (19)0.0256 (19)0.0088 (17)0.0120 (15)0.0093 (17)
C5BB0.0178 (19)0.0158 (16)0.0190 (16)0.0041 (14)0.0067 (13)0.0072 (14)
C3BB0.017 (2)0.0208 (17)0.0221 (18)0.0069 (15)0.0078 (14)0.0089 (15)
C2A0.019 (2)0.0214 (18)0.032 (2)0.0022 (16)0.0058 (16)0.0133 (17)
C2B0.014 (2)0.034 (2)0.038 (2)0.0055 (18)0.0094 (16)0.020 (2)
C3A0.016 (2)0.028 (2)0.031 (2)0.0050 (16)0.0104 (15)0.0172 (18)
O130.027 (2)0.047 (2)0.090 (4)0.0095 (18)0.030 (2)0.043 (2)
C7A0.023 (2)0.0181 (18)0.032 (2)0.0001 (16)0.0096 (16)0.0109 (17)
C5B0.026 (2)0.0156 (16)0.0233 (19)0.0044 (16)0.0083 (15)0.0067 (15)
C1A0.0139 (18)0.0171 (17)0.030 (2)0.0028 (14)0.0060 (14)0.0114 (15)
O120.043 (3)0.073 (3)0.043 (2)0.004 (2)0.0069 (18)0.026 (2)
O110.047 (3)0.0230 (18)0.099 (4)0.0105 (18)0.026 (3)0.023 (2)
Geometric parameters (Å, °) top
Ag—N2A2.261 (3)C5AA—C5A1.478 (6)
Ag—N1B2.331 (4)C8BB—C5BB1.403 (5)
Ag—N2B2.349 (3)C6B—C7B1.375 (6)
Ag—N1A2.453 (4)C6B—C5BB1.397 (6)
Cl—O131.385 (4)C6B—H6BA0.9300
Cl—O111.404 (4)C3AA—C3A1.388 (5)
Cl—O141.439 (4)C3AA—C4A1.492 (6)
Cl—O121.485 (5)C7B—C8B1.398 (6)
O1A—C4A1.220 (5)C7B—H7BA0.9300
C9BB—N1B1.345 (5)O2A—C5A1.215 (5)
C9BB—C3BB1.389 (6)C4B—C3BB1.500 (6)
C9BB—C8BB1.487 (6)C4B—C5B1.537 (7)
N2B—C8B1.329 (6)C3B—C3BB1.386 (6)
N2B—C8BB1.346 (5)C3B—C2B1.387 (6)
N1B—C1B1.347 (6)C3B—H3BA0.9300
C9AA—N1A1.341 (5)C6A—C7A1.369 (6)
C9AA—C3AA1.392 (5)C6A—H6AA0.9300
C9AA—C8AA1.488 (5)N1A—C1A1.351 (5)
O2B—C5B1.207 (5)C5A—C4A1.527 (6)
N2A—C8AA1.339 (5)C8B—H8BA0.9300
N2A—C8A1.344 (5)C5BB—C5B1.475 (6)
O1B—C4B1.204 (5)C2A—C3A1.379 (6)
C8A—C7A1.381 (6)C2A—C1A1.383 (6)
C8A—H8AA0.9300C2A—H2AA0.9300
C1B—C2B1.380 (6)C2B—H2BA0.9300
C1B—H1BA0.9300C3A—H3AA0.9300
C5AA—C8AA1.396 (5)C7A—H7AA0.9300
C5AA—C6A1.399 (6)C1A—H1AA0.9300
N2A—Ag—N1B129.69 (12)O1B—C4B—C3BB122.1 (4)
N2A—Ag—N2B158.05 (13)O1B—C4B—C5B120.0 (4)
N1B—Ag—N2B71.16 (12)C3BB—C4B—C5B117.9 (4)
N2A—Ag—N1A70.77 (11)C3BB—C3B—C2B118.4 (4)
N1B—Ag—N1A144.28 (12)C3BB—C3B—H3BA120.8
N2B—Ag—N1A95.79 (12)C2B—C3B—H3BA120.8
O13—Cl—O11115.7 (3)C7A—C6A—C5AA118.8 (4)
O13—Cl—O14111.8 (2)C7A—C6A—H6AA120.6
O11—Cl—O14110.3 (3)C5AA—C6A—H6AA120.6
O13—Cl—O12105.8 (3)C9AA—N1A—C1A117.8 (4)
O11—Cl—O12105.6 (3)C9AA—N1A—Ag113.5 (2)
O14—Cl—O12106.9 (3)C1A—N1A—Ag127.8 (3)
N1B—C9BB—C3BB122.2 (4)N2A—C8AA—C5AA121.3 (4)
N1B—C9BB—C8BB116.7 (4)N2A—C8AA—C9AA118.2 (3)
C3BB—C9BB—C8BB121.1 (4)C5AA—C8AA—C9AA120.4 (4)
C8B—N2B—C8BB119.0 (4)O2A—C5A—C5AA123.5 (4)
C8B—N2B—Ag124.3 (3)O2A—C5A—C4A119.2 (4)
C8BB—N2B—Ag116.1 (3)C5AA—C5A—C4A117.1 (3)
C9BB—N1B—C1B117.7 (4)O1A—C4A—C3AA122.7 (4)
C9BB—N1B—Ag117.6 (3)O1A—C4A—C5A119.9 (4)
C1B—N1B—Ag124.6 (3)C3AA—C4A—C5A117.3 (4)
N1A—C9AA—C3AA121.4 (3)N2B—C8B—C7B123.5 (4)
N1A—C9AA—C8AA117.1 (4)N2B—C8B—H8BA118.2
C3AA—C9AA—C8AA121.5 (4)C7B—C8B—H8BA118.2
C8AA—N2A—C8A118.5 (3)C6B—C5BB—C8BB118.6 (4)
C8AA—N2A—Ag119.7 (2)C6B—C5BB—C5B119.9 (4)
C8A—N2A—Ag121.8 (3)C8BB—C5BB—C5B121.5 (4)
N2A—C8A—C7A123.3 (4)C3B—C3BB—C9BB119.5 (4)
N2A—C8A—H8AA118.4C3B—C3BB—C4B119.7 (4)
C7A—C8A—H8AA118.4C9BB—C3BB—C4B120.8 (4)
N1B—C1B—C2B123.2 (4)C3A—C2A—C1A118.0 (4)
N1B—C1B—H1BA118.4C3A—C2A—H2AA121.0
C2B—C1B—H1BA118.4C1A—C2A—H2AA121.0
C8AA—C5AA—C6A119.3 (4)C1B—C2B—C3B118.9 (4)
C8AA—C5AA—C5A120.6 (4)C1B—C2B—H2BA120.6
C6A—C5AA—C5A120.1 (4)C3B—C2B—H2BA120.6
N2B—C8BB—C5BB121.3 (4)C2A—C3A—C3AA118.8 (4)
N2B—C8BB—C9BB117.8 (3)C2A—C3A—H3AA120.6
C5BB—C8BB—C9BB120.8 (4)C3AA—C3A—H3AA120.6
C7B—C6B—C5BB119.8 (4)C6A—C7A—C8A118.7 (4)
C7B—C6B—H6BA120.1C6A—C7A—H7AA120.6
C5BB—C6B—H6BA120.1C8A—C7A—H7AA120.6
C3A—C3AA—C9AA120.0 (4)O2B—C5B—C5BB123.2 (4)
C3A—C3AA—C4A120.2 (4)O2B—C5B—C4B119.2 (4)
C9AA—C3AA—C4A119.8 (4)C5BB—C5B—C4B117.5 (3)
C6B—C7B—C8B117.7 (4)N1A—C1A—C2A123.9 (4)
C6B—C7B—H7BA121.1N1A—C1A—H1AA118.0
C8B—C7B—H7BA121.1C2A—C1A—H1AA118.0
N2A—Ag—N2B—C8B19.0 (5)C5A—C5AA—C8AA—N2A177.0 (4)
N1B—Ag—N2B—C8B−177.5 (4)C6A—C5AA—C8AA—C9AA−179.7 (4)
N1A—Ag—N2B—C8B−31.7 (4)C5A—C5AA—C8AA—C9AA−0.6 (6)
N2A—Ag—N2B—C8BB−170.1 (3)N1A—C9AA—C8AA—N2A−5.4 (5)
N1B—Ag—N2B—C8BB−6.6 (3)C3AA—C9AA—C8AA—N2A173.7 (4)
N1A—Ag—N2B—C8BB139.2 (3)N1A—C9AA—C8AA—C5AA172.3 (4)
C3BB—C9BB—N1B—C1B−1.3 (6)C3AA—C9AA—C8AA—C5AA−8.5 (6)
C8BB—C9BB—N1B—C1B177.5 (3)C8AA—C5AA—C5A—O2A−161.6 (4)
C3BB—C9BB—N1B—Ag−179.1 (3)C6A—C5AA—C5A—O2A17.5 (7)
C8BB—C9BB—N1B—Ag−0.3 (4)C8AA—C5AA—C5A—C4A15.2 (6)
N2A—Ag—N1B—C9BB175.6 (3)C6A—C5AA—C5A—C4A−165.7 (4)
N2B—Ag—N1B—C9BB3.5 (3)C3A—C3AA—C4A—O1A11.3 (6)
N1A—Ag—N1B—C9BB−69.5 (4)C9AA—C3AA—C4A—O1A−169.4 (4)
N2A—Ag—N1B—C1B−2.0 (4)C3A—C3AA—C4A—C5A−166.4 (4)
N2B—Ag—N1B—C1B−174.1 (4)C9AA—C3AA—C4A—C5A12.9 (6)
N1A—Ag—N1B—C1B112.9 (3)O2A—C5A—C4A—O1A−21.9 (7)
N1B—Ag—N2A—C8AA150.5 (3)C5AA—C5A—C4A—O1A161.0 (4)
N2B—Ag—N2A—C8AA−50.0 (5)O2A—C5A—C4A—C3AA155.9 (4)
N1A—Ag—N2A—C8AA4.6 (3)C5AA—C5A—C4A—C3AA−21.2 (5)
N1B—Ag—N2A—C8A−30.2 (4)C8BB—N2B—C8B—C7B0.2 (6)
N2B—Ag—N2A—C8A129.3 (4)Ag—N2B—C8B—C7B170.8 (3)
N1A—Ag—N2A—C8A−176.1 (3)C6B—C7B—C8B—N2B0.1 (7)
C8AA—N2A—C8A—C7A0.7 (6)C7B—C6B—C5BB—C8BB−2.4 (6)
Ag—N2A—C8A—C7A−178.5 (3)C7B—C6B—C5BB—C5B177.6 (4)
C9BB—N1B—C1B—C2B−0.2 (6)N2B—C8BB—C5BB—C6B2.8 (6)
Ag—N1B—C1B—C2B177.4 (3)C9BB—C8BB—C5BB—C6B−179.4 (4)
C8B—N2B—C8BB—C5BB−1.7 (6)N2B—C8BB—C5BB—C5B−177.2 (4)
Ag—N2B—C8BB—C5BB−173.1 (3)C9BB—C8BB—C5BB—C5B0.6 (6)
C8B—N2B—C8BB—C9BB−179.5 (4)C2B—C3B—C3BB—C9BB−1.3 (6)
Ag—N2B—C8BB—C9BB9.1 (4)C2B—C3B—C3BB—C4B178.7 (4)
N1B—C9BB—C8BB—N2B−6.0 (5)N1B—C9BB—C3BB—C3B2.1 (6)
C3BB—C9BB—C8BB—N2B172.9 (4)C8BB—C9BB—C3BB—C3B−176.7 (4)
N1B—C9BB—C8BB—C5BB176.2 (3)N1B—C9BB—C3BB—C4B−177.9 (4)
C3BB—C9BB—C8BB—C5BB−5.0 (6)C8BB—C9BB—C3BB—C4B3.3 (6)
N1A—C9AA—C3AA—C3A0.3 (6)O1B—C4B—C3BB—C3B1.3 (7)
C8AA—C9AA—C3AA—C3A−178.8 (4)C5B—C4B—C3BB—C3B−177.7 (4)
N1A—C9AA—C3AA—C4A−179.0 (4)O1B—C4B—C3BB—C9BB−178.7 (4)
C8AA—C9AA—C3AA—C4A1.9 (6)C5B—C4B—C3BB—C9BB2.3 (6)
C5BB—C6B—C7B—C8B1.0 (6)N1B—C1B—C2B—C3B0.9 (7)
C8AA—C5AA—C6A—C7A0.9 (6)C3BB—C3B—C2B—C1B−0.1 (6)
C5A—C5AA—C6A—C7A−178.2 (4)C1A—C2A—C3A—C3AA−0.7 (6)
C3AA—C9AA—N1A—C1A−0.1 (6)C9AA—C3AA—C3A—C2A0.1 (6)
C8AA—C9AA—N1A—C1A179.1 (3)C4A—C3AA—C3A—C2A179.4 (4)
C3AA—C9AA—N1A—Ag−170.2 (3)C5AA—C6A—C7A—C8A1.0 (6)
C8AA—C9AA—N1A—Ag9.0 (4)N2A—C8A—C7A—C6A−1.9 (7)
N2A—Ag—N1A—C9AA−7.3 (3)C6B—C5BB—C5B—O2B4.6 (6)
N1B—Ag—N1A—C9AA−139.6 (3)C8BB—C5BB—C5B—O2B−175.4 (4)
N2B—Ag—N1A—C9AA154.9 (3)C6B—C5BB—C5B—C4B−175.1 (4)
N2A—Ag—N1A—C1A−176.1 (4)C8BB—C5BB—C5B—C4B4.9 (6)
N1B—Ag—N1A—C1A51.5 (4)O1B—C4B—C5B—O2B−5.0 (7)
N2B—Ag—N1A—C1A−14.0 (3)C3BB—C4B—C5B—O2B173.9 (4)
C8A—N2A—C8AA—C5AA1.3 (6)O1B—C4B—C5B—C5BB174.7 (4)
Ag—N2A—C8AA—C5AA−179.4 (3)C3BB—C4B—C5B—C5BB−6.4 (6)
C8A—N2A—C8AA—C9AA179.0 (3)C9AA—N1A—C1A—C2A−0.6 (6)
Ag—N2A—C8AA—C9AA−1.7 (5)Ag—N1A—C1A—C2A167.9 (3)
C6A—C5AA—C8AA—N2A−2.1 (6)C3A—C2A—C1A—N1A1.0 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8A—H8AA···O1Bi0.932.543.170 (5)125
C1B—H1BA···O14ii0.932.503.380 (5)157
C8B—H8BA···O11i0.932.583.155 (6)121
C1A—H1AA···O2Biii0.932.473.159 (5)131
C6B—H6BA···O2Aiv0.932.473.203 (5)136
C6A—H6AA···O13v0.932.453.235 (6)142
C8B—H8BA···O1Avi0.932.483.158 (6)130
C2A—H2AA···O12vii0.932.553.268 (6)134
C3A—H3AA···O11vii0.932.573.464 (7)162
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x+1, y+1, z+1; (v) x, y−1, z−1; (vi) −x+1, −y+1, −z; (vii) x+1, y, z−1.
Table 1
Selected geometric parameters (Å, °) top
Ag—N2A2.261 (3)Ag—N2B2.349 (3)
Ag—N1B2.331 (4)Ag—N1A2.453 (4)
N2A—Ag—N1B129.69 (12)N2A—Ag—N1A70.77 (11)
N2A—Ag—N2B158.05 (13)N1B—Ag—N1A144.28 (12)
N1B—Ag—N2B71.16 (12)N2B—Ag—N1A95.79 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8A—H8AA···O1Bi0.932.543.170 (5)125
C1B—H1BA···O14ii0.932.503.380 (5)157
C8B—H8BA···O11i0.932.583.155 (6)121
C1A—H1AA···O2Biii0.932.473.159 (5)131
C6B—H6BA···O2Aiv0.932.473.203 (5)136
C6A—H6AA···O13v0.932.453.235 (6)142
C8B—H8BA···O1Avi0.932.483.158 (6)130
C2A—H2AA···O12vii0.932.553.268 (6)134
C3A—H3AA···O11vii0.932.573.464 (7)162
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x+1, y+1, z+1; (v) x, y−1, z−1; (vi) −x+1, −y+1, −z; (vii) x+1, y, z−1.
Acknowledgements top

RJB acknowledges the Laboratory for the Structure of Matter at the Naval Research Laboratory for access to their diffractometers.

references
References top

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