The crystal structure determination of the title complex, [Ag2(C7H5O2)2(C6H12N2)]n, reveals a slightly distorted T geometry for the AgI atom, coordinated by an N atom from a 1,4-diazabicyclo[2.2.2]octane ligand and two O atoms from two benzoate anions. The dibenzoatodisilver(I) and 1,4-diazabicyclo[2.2.2]octane units lie across crystallographic inversion centres. The carboxyl groups in the complex behave in a η1:η1:μ2 fashion, bridging adjacent Ag atoms to form one-dimensional chains.
Supporting information
CCDC reference: 239069
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.055
- wR factor = 0.148
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact N1 .. N1 .. 2.59 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C9 .. 2.43 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C8 .. 2.45 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C10 .. 2.48 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C8' .. 2.52 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C10' .. 2.53 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact N1 .. C9' .. 2.55 Ang.
Alert level C
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C10
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
7 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: R3m Software (Siemens, 1990); cell refinement: R3m Software; data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.
catena-poly[[di-µ-benzoato-
κ4O:
O'-disilver(I)]-µ-1,4-
diazabicyclo[2.2.2]octane-
κ2N:
N']
top
Crystal data top
C20H22Ag2N2O4 | F(000) = 564 |
Mr = 570.14 | Dx = 1.862 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 6.243 (5) Å | θ = 4.0–27.0° |
b = 16.459 (5) Å | µ = 1.95 mm−1 |
c = 10.084 (5) Å | T = 293 K |
β = 101.13 (4)° | Needle, colourless |
V = 1016.7 (10) Å3 | 0.42 × 0.38 × 0.34 mm |
Z = 2 | |
Data collection top
Siemens R3m diffractometer | 1298 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 28.0°, θmin = 2.4° |
ω scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→21 |
Tmin = 0.457, Tmax = 0.515 | l = −13→13 |
2672 measured reflections | 2 standard reflections every 118 reflections |
2460 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.02 | |
2460 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.56 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ag1 | 0.03201 (11) | 0.02300 (4) | 0.36888 (5) | 0.0659 (3) | |
O1 | −0.2951 (9) | 0.0782 (4) | 0.3557 (5) | 0.0654 (15) | |
O2 | −0.2986 (9) | 0.0673 (3) | 0.5774 (4) | 0.0626 (14) | |
C1 | −0.3743 (12) | 0.0934 (4) | 0.4594 (7) | 0.0522 (18) | |
C2 | −0.5725 (13) | 0.1474 (4) | 0.4420 (7) | 0.0522 (18) | |
C3 | −0.6234 (15) | 0.1976 (5) | 0.3313 (8) | 0.071 (2) | |
H3A | −0.5311 | 0.1974 | 0.2654 | 0.080* | |
C4 | −0.8017 (18) | 0.2481 (6) | 0.3164 (12) | 0.096 (3) | |
H4A | −0.8342 | 0.2827 | 0.2385 | 0.080* | |
C5 | −0.9356 (17) | 0.2495 (7) | 0.4104 (13) | 0.096 (3) | |
H5A | −1.0612 | 0.2844 | 0.3975 | 0.080* | |
C6 | −0.8842 (16) | 0.1992 (6) | 0.5226 (11) | 0.084 (3) | |
H6A | −0.9761 | 0.2001 | 0.5887 | 0.080* | |
C7 | −0.7022 (14) | 0.1480 (5) | 0.5398 (8) | 0.067 (2) | |
H7A | −0.6654 | 0.1141 | 0.6184 | 0.080* | |
N1 | 0.0143 (11) | 0.0121 (4) | 0.1282 (5) | 0.0576 (17) | |
C8 | −0.216 (3) | 0.0177 (16) | 0.0516 (15) | 0.079 (5) | 0.50 |
H8A | −0.2640 | 0.0721 | 0.0646 | 0.080* | 0.50 |
H8B | −0.3099 | −0.0192 | 0.0874 | 0.080* | 0.50 |
C8' | −0.092 (4) | 0.0811 (11) | 0.0550 (14) | 0.069 (5) | 0.50 |
H8'A | −0.0177 | 0.1314 | 0.0807 | 0.080* | 0.50 |
H8'B | −0.2348 | 0.0837 | 0.0774 | 0.080* | 0.50 |
C9 | 0.103 (5) | −0.0657 (13) | 0.0987 (17) | 0.091 (7) | 0.50 |
H9A | 0.0389 | −0.1103 | 0.1387 | 0.080* | 0.50 |
H9B | 0.2536 | −0.0620 | 0.1415 | 0.080* | 0.50 |
C9' | −0.121 (3) | −0.0619 (13) | 0.0894 (17) | 0.071 (5) | 0.50 |
H9'A | −0.2638 | −0.0531 | 0.1089 | 0.080* | 0.50 |
H9'B | −0.0547 | −0.1069 | 0.1425 | 0.080* | 0.50 |
C10 | 0.137 (4) | 0.0778 (13) | 0.0648 (15) | 0.084 (6) | 0.50 |
H10A | 0.2866 | 0.0790 | 0.1105 | 0.080* | 0.50 |
H10B | 0.0710 | 0.1292 | 0.0775 | 0.080* | 0.50 |
C10' | 0.230 (3) | −0.0050 (13) | 0.1035 (13) | 0.067 (5) | 0.50 |
H10C | 0.2876 | −0.0518 | 0.1551 | 0.080* | 0.50 |
H10D | 0.3250 | 0.0402 | 0.1315 | 0.080* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0827 (5) | 0.0825 (5) | 0.0324 (3) | 0.0164 (4) | 0.0110 (3) | 0.0007 (3) |
O1 | 0.071 (4) | 0.085 (4) | 0.040 (3) | 0.009 (3) | 0.010 (3) | −0.002 (3) |
O2 | 0.068 (4) | 0.081 (4) | 0.038 (2) | 0.010 (3) | 0.007 (2) | 0.004 (3) |
C1 | 0.063 (5) | 0.054 (4) | 0.039 (3) | −0.009 (4) | 0.007 (3) | −0.002 (3) |
C2 | 0.063 (5) | 0.044 (4) | 0.048 (4) | −0.001 (4) | 0.006 (4) | −0.009 (3) |
C3 | 0.085 (6) | 0.061 (5) | 0.065 (5) | 0.010 (5) | 0.008 (5) | 0.009 (4) |
C4 | 0.098 (8) | 0.074 (7) | 0.103 (8) | 0.018 (6) | −0.015 (7) | 0.013 (6) |
C5 | 0.073 (7) | 0.073 (7) | 0.133 (10) | 0.014 (6) | −0.001 (7) | −0.016 (7) |
C6 | 0.068 (6) | 0.077 (6) | 0.112 (8) | −0.004 (5) | 0.027 (6) | −0.028 (6) |
C7 | 0.073 (6) | 0.068 (5) | 0.063 (5) | −0.007 (5) | 0.022 (4) | −0.010 (4) |
N1 | 0.071 (5) | 0.068 (4) | 0.031 (3) | 0.018 (4) | 0.004 (3) | −0.004 (3) |
C8 | 0.069 (12) | 0.124 (17) | 0.039 (8) | 0.019 (13) | 0.003 (8) | −0.001 (11) |
C8' | 0.098 (15) | 0.078 (12) | 0.033 (7) | 0.015 (11) | 0.016 (9) | −0.005 (8) |
C9 | 0.15 (2) | 0.065 (12) | 0.053 (10) | 0.019 (15) | 0.012 (12) | 0.001 (10) |
C9' | 0.065 (11) | 0.098 (14) | 0.055 (9) | −0.027 (12) | 0.023 (9) | −0.004 (10) |
C10 | 0.095 (15) | 0.110 (17) | 0.043 (9) | −0.014 (13) | 0.004 (9) | −0.018 (10) |
C10' | 0.076 (12) | 0.095 (14) | 0.025 (6) | 0.025 (10) | 0.000 (7) | −0.007 (7) |
Geometric parameters (Å, º) top
Ag1—O1 | 2.216 (6) | N1—C10' | 1.444 (18) |
Ag1—O2i | 2.219 (5) | N1—C9 | 1.45 (2) |
Ag1—N1 | 2.415 (5) | N1—C8' | 1.445 (17) |
Ag1—Ag1i | 2.8520 (17) | N1—C9' | 1.490 (19) |
O1—C1 | 1.264 (8) | N1—C8 | 1.500 (17) |
O2—C1 | 1.268 (8) | N1—C10 | 1.53 (2) |
O2—Ag1i | 2.219 (5) | C8—H8A | 0.96 |
C1—C2 | 1.506 (10) | C8—H8B | 0.96 |
C2—C3 | 1.376 (10) | C8'—H8'A | 0.96 |
C2—C7 | 1.392 (10) | C8'—H8'B | 0.96 |
C3—C4 | 1.374 (12) | C9—H9A | 0.96 |
C3—H3A | 0.96 | C9—H9B | 0.96 |
C4—C5 | 1.379 (15) | C9'—H9'A | 0.96 |
C4—H4A | 0.96 | C9'—H9'B | 0.96 |
C5—C6 | 1.389 (14) | C10—H10A | 0.96 |
C5—H5A | 0.96 | C10—H10B | 0.96 |
C6—C7 | 1.399 (12) | C10'—H10C | 0.96 |
C6—H6A | 0.96 | C10'—H10D | 0.96 |
C7—H7A | 0.96 | | |
| | | |
O1—Ag1—O2i | 158.2 (2) | C9'—C9—C8ii | 116.2 (15) |
O1—Ag1—N1 | 96.16 (19) | N1—C9—C8ii | 90.7 (13) |
O2i—Ag1—N1 | 94.73 (19) | C10'—C9—C10ii | 118.0 (15) |
O1—Ag1—Ag1i | 82.63 (13) | C9'—C9—C10ii | 50.8 (12) |
O2i—Ag1—Ag1i | 80.12 (12) | N1—C9—C10ii | 90.2 (13) |
N1—Ag1—Ag1i | 157.63 (18) | C8ii—C9—C10ii | 74.2 (10) |
C1—O1—Ag1 | 122.3 (5) | C10'—C9—H9A | 153.0 |
C1—O2—Ag1i | 125.6 (5) | C9'—C9—H9A | 64.4 |
O1—C1—O2 | 125.1 (7) | N1—C9—H9A | 112.6 |
O1—C1—C2 | 117.7 (6) | C8'ii—C9—H9A | 110.6 |
O2—C1—C2 | 117.3 (6) | C8ii—C9—H9A | 150.9 |
C3—C2—C7 | 119.7 (8) | C10ii—C9—H9A | 88.1 |
C3—C2—C1 | 120.3 (7) | C10'—C9—H9B | 51.7 |
C7—C2—C1 | 119.9 (7) | C9'—C9—H9B | 156.7 |
C4—C3—C2 | 120.5 (9) | N1—C9—H9B | 103.4 |
C4—C3—H3A | 120.6 | C8'ii—C9—H9B | 107.8 |
C2—C3—H3A | 118.9 | C8ii—C9—H9B | 81.5 |
C3—C4—C5 | 121.3 (10) | C10ii—C9—H9B | 152.3 |
C3—C4—H4A | 119.2 | H9A—C9—H9B | 108.1 |
C5—C4—H4A | 119.5 | C10'—C9—H9'B | 151.6 |
C6—C5—C4 | 118.3 (10) | N1—C9—H9'B | 92.7 |
C6—C5—H5A | 121.4 | C8'ii—C9—H9'B | 110.7 |
C4—C5—H5A | 120.3 | C8ii—C9—H9'B | 149.2 |
C5—C6—C7 | 121.0 (10) | C10ii—C9—H9'B | 75.1 |
C5—C6—H6A | 118.8 | H9B—C9—H9'B | 127.1 |
C7—C6—H6A | 120.2 | C10'—C9—H10C | 45.5 |
C2—C7—C6 | 119.1 (9) | C9'—C9—H10C | 152.3 |
C2—C7—H7A | 120.1 | N1—C9—H10C | 96.0 |
C6—C7—H7A | 120.8 | C8'ii—C9—H10C | 110.6 |
C10'—N1—C9 | 52.1 (12) | C8ii—C9—H10C | 80.3 |
C10'—N1—C8' | 114.7 (12) | C10ii—C9—H10C | 153.9 |
C9—N1—C8' | 138.3 (9) | H9A—C9—H10C | 112.5 |
C10'—N1—C9' | 107.1 (12) | H9'B—C9—H10C | 129.6 |
C9—N1—C9' | 56.1 (13) | C9—C9'—C8 | 114.5 (17) |
C8'—N1—C9' | 109.0 (13) | C9—C9'—N1 | 60.4 (11) |
C10'—N1—C8 | 139.3 (9) | C8—C9'—N1 | 61.1 (12) |
C9—N1—C8 | 108.3 (14) | C9—C9'—C10ii | 85.9 (15) |
C8'—N1—C8 | 52.2 (11) | C8—C9'—C10ii | 86.9 (15) |
C9'—N1—C8 | 58.4 (12) | N1—C9'—C10ii | 108.8 (13) |
C10'—N1—C10 | 60.6 (12) | C9—C9'—H8B | 151.6 |
C9—N1—C10 | 107.3 (14) | N1—C9'—H8B | 91.6 |
C8'—N1—C10 | 56.7 (11) | C10ii—C9'—H8B | 100.5 |
C9'—N1—C10 | 140.3 (9) | C8—C9'—H9A | 153.6 |
C8—N1—C10 | 104.4 (13) | N1—C9'—H9A | 92.7 |
C10'—N1—Ag1 | 109.0 (6) | C10ii—C9'—H9A | 100.0 |
C9—N1—Ag1 | 109.1 (7) | H8B—C9'—H9A | 156.4 |
C8'—N1—Ag1 | 112.5 (6) | C9—C9'—H9'A | 163.4 |
C9'—N1—Ag1 | 103.8 (7) | C8—C9'—H9'A | 64.5 |
C8—N1—Ag1 | 111.5 (7) | N1—C9'—H9'A | 109.0 |
C10—N1—Ag1 | 115.9 (7) | C10ii—C9'—H9'A | 110.3 |
C8'—C8—C9' | 120.3 (17) | H9A—C9'—H9'A | 133.6 |
C8'—C8—N1 | 61.7 (11) | C9—C9'—H9'B | 66.8 |
C9'—C8—N1 | 60.5 (10) | C8—C9'—H9'B | 161.7 |
C8'—C8—C10'ii | 92.9 (16) | N1—C9'—H9'B | 108.9 |
C9'—C8—C10'ii | 94.7 (15) | C10ii—C9'—H9'B | 111.3 |
N1—C8—C10'ii | 111.6 (13) | H8B—C9'—H9'B | 133.0 |
C8'—C8—C9ii | 52.6 (11) | H9'A—C9'—H9'B | 108.6 |
C9'—C8—C9ii | 111.9 (13) | C8'—C10—C10' | 112.9 (17) |
N1—C8—C9ii | 88.2 (12) | C8'—C10—N1 | 58.6 (10) |
C8'—C8—H8A | 56.3 | C10'—C10—N1 | 56.8 (11) |
C9'—C8—H8A | 157.3 | C8'—C10—C9'ii | 93.9 (14) |
N1—C8—H8A | 106.2 | C10'—C10—C9'ii | 93.0 (15) |
C10'ii—C8—H8A | 107.6 | N1—C10—C9'ii | 110.9 (13) |
C9ii—C8—H8A | 84.1 | C8'—C10—C9ii | 50.6 (11) |
C8'—C8—H8B | 154.6 | C10'—C10—C9ii | 108.2 (13) |
C9'—C8—H8B | 65.2 | N1—C10—C9ii | 85.4 (12) |
N1—C8—H8B | 111.1 | C10'—C10—H8'A | 144.9 |
C10'ii—C8—H8B | 111.8 | N1—C10—H8'A | 89.2 |
C9ii—C8—H8B | 152.0 | C9'ii—C10—H8'A | 108.7 |
H8A—C8—H8B | 108.2 | C9ii—C10—H8'A | 74.0 |
C8'—C8—H8'B | 46.0 | C8'—C10—H10A | 155.6 |
C9'—C8—H8'B | 149.2 | C10'—C10—H10A | 66.6 |
N1—C8—H8'B | 94.1 | N1—C10—H10A | 109.5 |
C10'ii—C8—H8'B | 111.8 | C9'ii—C10—H10A | 110.5 |
C9ii—C8—H8'B | 81.9 | C9ii—C10—H10A | 153.8 |
H8B—C8—H8'B | 115.3 | H8'A—C10—H10A | 125.9 |
C8'—C8—H9'A | 149.0 | C8'—C10—H10B | 61.5 |
N1—C8—H9'A | 89.7 | C10'—C10—H10B | 156.8 |
C10'ii—C8—H9'A | 109.7 | N1—C10—H10B | 107.8 |
C9ii—C8—H9'A | 144.6 | C9'ii—C10—H10B | 109.5 |
H8A—C8—H9'A | 130.1 | C9ii—C10—H10B | 85.8 |
H8'B—C8—H9'A | 133.5 | H10A—C10—H10B | 108.6 |
C8—C8'—C10 | 124.1 (19) | C8'—C10—H10D | 143.6 |
C8—C8'—N1 | 66.1 (12) | N1—C10—H10D | 85.9 |
C10—C8'—N1 | 64.8 (12) | C9'ii—C10—H10D | 107.0 |
C8—C8'—C9ii | 86.1 (15) | C9ii—C10—H10D | 141.4 |
C10—C8'—C9ii | 84.9 (15) | H8'A—C10—H10D | 143.3 |
N1—C8'—C9ii | 107.8 (13) | H10B—C10—H10D | 132.5 |
C8—C8'—H8A | 46.3 | C9—C10'—N1 | 64.1 (14) |
C10—C8'—H8A | 166.6 | C9—C10'—C10 | 119.6 (18) |
N1—C8'—H8A | 102.0 | N1—C10'—C10 | 62.6 (10) |
C9ii—C8'—H8A | 102.2 | C9—C10'—C8ii | 86.8 (15) |
C8—C8'—H8'A | 163.2 | N1—C10'—C8ii | 109.1 (12) |
C10—C8'—H8'A | 65.4 | C10—C10'—C8ii | 85.3 (13) |
N1—C8'—H8'A | 112.8 | C9—C10'—H9B | 48.1 |
C9ii—C8'—H8'A | 109.5 | N1—C10'—H9B | 100.8 |
H8A—C8'—H8'A | 121.4 | C10—C10'—H9B | 163.3 |
C8—C8'—H8'B | 57.7 | C8ii—C10'—H9B | 103.4 |
C10—C8'—H8'B | 162.7 | C9—C10'—H10A | 155.6 |
N1—C8'—H8'B | 105.7 | N1—C10'—H10A | 91.8 |
C9ii—C8'—H8'B | 112.3 | C8ii—C10'—H10A | 98.3 |
H8'A—C8'—H8'B | 108.7 | H9B—C10'—H10A | 149.5 |
C8—C8'—H10B | 163.1 | C9—C10'—H10C | 63.7 |
N1—C8'—H10B | 97.1 | N1—C10'—H10C | 109.1 |
C9ii—C8'—H10B | 99.0 | C10—C10'—H10C | 162.5 |
H8A—C8'—H10B | 145.4 | C8ii—C10'—H10C | 112.2 |
H8'B—C8'—H10B | 132.5 | H10A—C10'—H10C | 133.4 |
C10'—C9—C9' | 126 (2) | C9—C10'—H10D | 165.2 |
C10'—C9—N1 | 63.8 (12) | N1—C10'—H10D | 110.0 |
C9'—C9—N1 | 63.5 (13) | C10—C10'—H10D | 63.9 |
C10'—C9—C8'ii | 94.1 (17) | C8ii—C10'—H10D | 108.0 |
C9'—C9—C8'ii | 95.3 (17) | H9B—C10'—H10D | 124.7 |
N1—C9—C8'ii | 113.9 (14) | H10C—C10'—H10D | 108.5 |
C10'—C9—C8ii | 52.8 (12) | | |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z. |