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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037580/cs2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037580/cs2045Isup2.hkl
Contains datablock I

CCDC reference: 660080

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.066
  • wR factor = 0.184
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O14 .. C4B .. 2.84 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C9BB -C3BB 1.46 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4A - C5A ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4B - C5B ... 1.54 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C5A .. 2.94 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O14 .. C5B .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 20 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl O4
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

Structure description 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.

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).

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 = 627.70F(000) = 624
Triclinic, P1Dx = 1.899 Mg m3
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 = 2.6–29.9°
α = 112.525 (3)°µ = 1.10 mm1
β = 103.682 (4)°T = 93 K
γ = 97.378 (4)°Prism, 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)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 30.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1012
Tmin = 0.679, Tmax = 0.879k = 1515
11431 measured reflectionsl = 1817
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.107P)2]
where P = (Fo2 + 2Fc2)/3
6019 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 2.36 e Å3
0 restraintsΔρmin = 1.63 e Å3
Crystal data top
[Ag(C12H6N2O2)2]ClO4γ = 97.378 (4)°
Mr = 627.70V = 1097.8 (5) Å3
Triclinic, P1Z = 2
a = 8.493 (2) ÅMo Kα radiation
b = 11.260 (3) ŵ = 1.10 mm1
c = 13.190 (4) ÅT = 93 K
α = 112.525 (3)°0.38 × 0.32 × 0.12 mm
β = 103.682 (4)°
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)] = 0.0660 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.07Δρmax = 2.36 e Å3
6019 reflectionsΔρmin = 1.63 e Å3
343 parameters
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)
Cl0.44552 (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)
O140.6087 (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)
C8A0.0858 (5)0.2175 (4)0.0876 (4)0.0215 (8)
H8AA0.11220.22530.15410.026*
C1B0.1214 (5)0.5583 (4)0.4135 (4)0.0232 (8)
H1BA0.19160.48300.35000.028*
C5AA0.0150 (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*
O2A0.0645 (5)0.1084 (4)0.3101 (3)0.0352 (8)
C4B0.1929 (6)0.9039 (4)0.6977 (4)0.0223 (8)
C3B0.0743 (6)0.7283 (5)0.6016 (4)0.0248 (9)
H3BA0.10840.76880.66590.030*
C6A0.1213 (6)0.0888 (4)0.1098 (4)0.0239 (8)
H6AA0.16790.01120.17770.029*
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*
C2B0.1769 (6)0.6150 (4)0.5072 (4)0.0271 (9)
H2BA0.28140.57780.50690.033*
C3A0.3321 (5)0.5288 (4)0.0830 (4)0.0232 (8)
H3AA0.37040.52460.14440.028*
O130.3380 (5)0.7847 (4)0.7458 (4)0.0480 (11)
C7A0.1556 (6)0.0998 (4)0.0107 (4)0.0247 (9)
H7AA0.22450.02930.00970.030*
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*
O120.3734 (6)0.7661 (5)0.9063 (4)0.0550 (12)
O110.4590 (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, º) 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—C8B177.5 (4)C6A—C5AA—C8AA—C9AA179.7 (4)
N1A—Ag—N2B—C8B31.7 (4)C5A—C5AA—C8AA—C9AA0.6 (6)
N2A—Ag—N2B—C8BB170.1 (3)N1A—C9AA—C8AA—N2A5.4 (5)
N1B—Ag—N2B—C8BB6.6 (3)C3AA—C9AA—C8AA—N2A173.7 (4)
N1A—Ag—N2B—C8BB139.2 (3)N1A—C9AA—C8AA—C5AA172.3 (4)
C3BB—C9BB—N1B—C1B1.3 (6)C3AA—C9AA—C8AA—C5AA8.5 (6)
C8BB—C9BB—N1B—C1B177.5 (3)C8AA—C5AA—C5A—O2A161.6 (4)
C3BB—C9BB—N1B—Ag179.1 (3)C6A—C5AA—C5A—O2A17.5 (7)
C8BB—C9BB—N1B—Ag0.3 (4)C8AA—C5AA—C5A—C4A15.2 (6)
N2A—Ag—N1B—C9BB175.6 (3)C6A—C5AA—C5A—C4A165.7 (4)
N2B—Ag—N1B—C9BB3.5 (3)C3A—C3AA—C4A—O1A11.3 (6)
N1A—Ag—N1B—C9BB69.5 (4)C9AA—C3AA—C4A—O1A169.4 (4)
N2A—Ag—N1B—C1B2.0 (4)C3A—C3AA—C4A—C5A166.4 (4)
N2B—Ag—N1B—C1B174.1 (4)C9AA—C3AA—C4A—C5A12.9 (6)
N1A—Ag—N1B—C1B112.9 (3)O2A—C5A—C4A—O1A21.9 (7)
N1B—Ag—N2A—C8AA150.5 (3)C5AA—C5A—C4A—O1A161.0 (4)
N2B—Ag—N2A—C8AA50.0 (5)O2A—C5A—C4A—C3AA155.9 (4)
N1A—Ag—N2A—C8AA4.6 (3)C5AA—C5A—C4A—C3AA21.2 (5)
N1B—Ag—N2A—C8A30.2 (4)C8BB—N2B—C8B—C7B0.2 (6)
N2B—Ag—N2A—C8A129.3 (4)Ag—N2B—C8B—C7B170.8 (3)
N1A—Ag—N2A—C8A176.1 (3)C6B—C7B—C8B—N2B0.1 (7)
C8AA—N2A—C8A—C7A0.7 (6)C7B—C6B—C5BB—C8BB2.4 (6)
Ag—N2A—C8A—C7A178.5 (3)C7B—C6B—C5BB—C5B177.6 (4)
C9BB—N1B—C1B—C2B0.2 (6)N2B—C8BB—C5BB—C6B2.8 (6)
Ag—N1B—C1B—C2B177.4 (3)C9BB—C8BB—C5BB—C6B179.4 (4)
C8B—N2B—C8BB—C5BB1.7 (6)N2B—C8BB—C5BB—C5B177.2 (4)
Ag—N2B—C8BB—C5BB173.1 (3)C9BB—C8BB—C5BB—C5B0.6 (6)
C8B—N2B—C8BB—C9BB179.5 (4)C2B—C3B—C3BB—C9BB1.3 (6)
Ag—N2B—C8BB—C9BB9.1 (4)C2B—C3B—C3BB—C4B178.7 (4)
N1B—C9BB—C8BB—N2B6.0 (5)N1B—C9BB—C3BB—C3B2.1 (6)
C3BB—C9BB—C8BB—N2B172.9 (4)C8BB—C9BB—C3BB—C3B176.7 (4)
N1B—C9BB—C8BB—C5BB176.2 (3)N1B—C9BB—C3BB—C4B177.9 (4)
C3BB—C9BB—C8BB—C5BB5.0 (6)C8BB—C9BB—C3BB—C4B3.3 (6)
N1A—C9AA—C3AA—C3A0.3 (6)O1B—C4B—C3BB—C3B1.3 (7)
C8AA—C9AA—C3AA—C3A178.8 (4)C5B—C4B—C3BB—C3B177.7 (4)
N1A—C9AA—C3AA—C4A179.0 (4)O1B—C4B—C3BB—C9BB178.7 (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—C1B0.1 (6)
C5A—C5AA—C6A—C7A178.2 (4)C1A—C2A—C3A—C3AA0.7 (6)
C3AA—C9AA—N1A—C1A0.1 (6)C9AA—C3AA—C3A—C2A0.1 (6)
C8AA—C9AA—N1A—C1A179.1 (3)C4A—C3AA—C3A—C2A179.4 (4)
C3AA—C9AA—N1A—Ag170.2 (3)C5AA—C6A—C7A—C8A1.0 (6)
C8AA—C9AA—N1A—Ag9.0 (4)N2A—C8A—C7A—C6A1.9 (7)
N2A—Ag—N1A—C9AA7.3 (3)C6B—C5BB—C5B—O2B4.6 (6)
N1B—Ag—N1A—C9AA139.6 (3)C8BB—C5BB—C5B—O2B175.4 (4)
N2B—Ag—N1A—C9AA154.9 (3)C6B—C5BB—C5B—C4B175.1 (4)
N2A—Ag—N1A—C1A176.1 (4)C8BB—C5BB—C5B—C4B4.9 (6)
N1B—Ag—N1A—C1A51.5 (4)O1B—C4B—C5B—O2B5.0 (7)
N2B—Ag—N1A—C1A14.0 (3)C3BB—C4B—C5B—O2B173.9 (4)
C8A—N2A—C8AA—C5AA1.3 (6)O1B—C4B—C5B—C5BB174.7 (4)
Ag—N2A—C8AA—C5AA179.4 (3)C3BB—C4B—C5B—C5BB6.4 (6)
C8A—N2A—C8AA—C9AA179.0 (3)C9AA—N1A—C1A—C2A0.6 (6)
Ag—N2A—C8AA—C9AA1.7 (5)Ag—N1A—C1A—C2A167.9 (3)
C6A—C5AA—C8AA—N2A2.1 (6)C3A—C2A—C1A—N1A1.0 (6)
Hydrogen-bond geometry (Å, º) 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) x1, y+1, z+1; (iii) x+1, y+2, z+1; (iv) x+1, y+1, z+1; (v) x, y1, z1; (vi) x+1, y+1, z; (vii) x+1, y, z1.

Experimental details

Crystal data
Chemical formula[Ag(C12H6N2O2)2]ClO4
Mr627.70
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)8.493 (2), 11.260 (3), 13.190 (4)
α, β, γ (°)112.525 (3), 103.682 (4), 97.378 (4)
V3)1097.8 (5)
Z2
Radiation typeMo Kα
µ (mm1)1.10
Crystal size (mm)0.38 × 0.32 × 0.12
Data collection
DiffractometerBruker APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.679, 0.879
No. of measured, independent and
observed [I > 2σ(I)] reflections
11431, 6019, 4791
Rint0.067
(sin θ/λ)max1)0.711
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.184, 1.07
No. of reflections6019
No. of parameters343
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.36, 1.63

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) 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)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8A—H8AA···O1Bi0.932.543.170 (5)125.2
C1B—H1BA···O14ii0.932.503.380 (5)157.4
C8B—H8BA···O11i0.932.583.155 (6)120.8
C1A—H1AA···O2Biii0.932.473.159 (5)131.4
C6B—H6BA···O2Aiv0.932.473.203 (5)136.1
C6A—H6AA···O13v0.932.453.235 (6)142.1
C8B—H8BA···O1Avi0.932.483.158 (6)129.6
C2A—H2AA···O12vii0.932.553.268 (6)134.3
C3A—H3AA···O11vii0.932.573.464 (7)162.4
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y+1, z+1; (iii) x+1, y+2, z+1; (iv) x+1, y+1, z+1; (v) x, y1, z1; (vi) x+1, y+1, z; (vii) x+1, y, z1.
 

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