The title complex, [Ag
2(C
7H
4ClO
2)
2(C
5H
6N
2)
2]·H
2O, lies about an inversion center, with the water molecule on a twofold rotation axis, and the Ag
I atom is three-coordinated by two O atoms from two different but symmetry-related 4-chlorobenzoate anions and one N atom from one 2-aminopyridine ligand. The 4-chlorobenzoate anion acts as a bidentate ligand, bridging two inversion-related Ag atoms of the complex and forming a dimer. In the crystal structure, the molecules are linked through intramolecular and intermolecular N—H
O and O—H
O hydrogen bonds, forming two-dimensional layers parallel to the
bc plane.
Supporting information
CCDC reference: 258675
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.053
- wR factor = 0.119
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and PLATON (Spek, 2004); software used to prepare material for publication: SHELXTL.
Bis(µ-4-chlorobenzoato-
κ2O:
O')bis[(2-aminopyridine-
κN)silver(I)](Ag—Ag) monohydrate
top
Crystal data top
[Ag2(C7H4ClO2)2(C5H6N2)2]·H2O | F(000) = 1448 |
Mr = 733.10 | Dx = 1.859 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1127 reflections |
a = 27.387 (2) Å | θ = 2.4–23.6° |
b = 5.504 (3) Å | µ = 1.74 mm−1 |
c = 17.879 (2) Å | T = 293 K |
β = 103.630 (2)° | Block, colorless |
V = 2619.2 (15) Å3 | 0.15 × 0.12 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2843 independent reflections |
Radiation source: fine-focus sealed tube | 2598 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −34→34 |
Tmin = 0.780, Tmax = 0.845 | k = −7→7 |
13354 measured reflections | l = −22→22 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.23 | w = 1/[σ2(Fo2) + (0.0498P)2 + 4.3842P] where P = (Fo2 + 2Fc2)/3 |
2843 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.81 e Å−3 |
0 restraints | Δρmin = −0.52 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 | |
Ag1 | 1.027212 (14) | 0.28951 (7) | 0.48340 (2) | 0.05938 (17) | |
Cl1 | 0.75159 (5) | 0.1841 (3) | 0.10424 (9) | 0.0848 (5) | |
O1 | 0.96204 (14) | 0.2524 (6) | 0.3821 (2) | 0.0617 (9) | |
O2 | 0.92083 (13) | 0.5730 (7) | 0.41147 (19) | 0.0665 (10) | |
H2A | 1.0099 | −0.2994 | 0.3258 | 0.084* | |
H2B | 0.9984 | −0.0822 | 0.3608 | 0.102* | |
O1W | 1.0000 | 0.3873 (10) | 0.2500 | 0.0788 (15) | |
H1W | 0.9864 | 0.2985 | 0.2808 | 0.080* | |
N1 | 1.08071 (14) | −0.0233 (7) | 0.4617 (2) | 0.0530 (9) | |
N2 | 1.02398 (19) | −0.1785 (9) | 0.3572 (3) | 0.0799 (14) | |
C1 | 0.88113 (16) | 0.3357 (8) | 0.3057 (2) | 0.0448 (9) | |
C2 | 0.88092 (19) | 0.1317 (9) | 0.2600 (3) | 0.0619 (12) | |
H2 | 0.9080 | 0.0249 | 0.2711 | 0.074* | |
C3 | 0.8413 (2) | 0.0854 (10) | 0.1987 (3) | 0.0654 (13) | |
H3 | 0.8416 | −0.0512 | 0.1682 | 0.079* | |
C4 | 0.80151 (18) | 0.2410 (9) | 0.1829 (3) | 0.0561 (12) | |
C5 | 0.80048 (18) | 0.4428 (10) | 0.2270 (3) | 0.0658 (13) | |
H5 | 0.7731 | 0.5478 | 0.2158 | 0.079* | |
C6 | 0.84035 (18) | 0.4888 (10) | 0.2881 (3) | 0.0602 (12) | |
H6 | 0.8397 | 0.6261 | 0.3182 | 0.072* | |
C7 | 0.92452 (16) | 0.3916 (8) | 0.3720 (2) | 0.0470 (9) | |
C8 | 1.0689 (2) | −0.1959 (8) | 0.4085 (3) | 0.0567 (12) | |
C9 | 1.1023 (2) | −0.3862 (9) | 0.4041 (3) | 0.0642 (13) | |
H9 | 1.0934 | −0.5079 | 0.3673 | 0.077* | |
C10 | 1.1477 (2) | −0.3884 (11) | 0.4547 (3) | 0.0730 (15) | |
H10 | 1.1703 | −0.5128 | 0.4526 | 0.088* | |
C11 | 1.1607 (2) | −0.2085 (11) | 0.5092 (4) | 0.0755 (16) | |
H11 | 1.1920 | −0.2084 | 0.5438 | 0.091* | |
C12 | 1.1265 (2) | −0.0310 (10) | 0.5108 (3) | 0.0653 (13) | |
H12 | 1.1350 | 0.0912 | 0.5475 | 0.078* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0618 (3) | 0.0602 (3) | 0.0505 (2) | 0.01167 (17) | 0.00194 (17) | −0.01571 (16) |
Cl1 | 0.0621 (8) | 0.1214 (13) | 0.0622 (8) | −0.0244 (8) | −0.0024 (6) | −0.0081 (8) |
O1 | 0.060 (2) | 0.063 (2) | 0.056 (2) | 0.0128 (16) | 0.0023 (16) | −0.0144 (15) |
O2 | 0.065 (2) | 0.070 (2) | 0.058 (2) | 0.0101 (17) | 0.0033 (16) | −0.0270 (17) |
O1W | 0.101 (4) | 0.071 (3) | 0.073 (3) | 0.000 | 0.037 (3) | 0.000 |
N1 | 0.061 (2) | 0.045 (2) | 0.055 (2) | 0.0099 (17) | 0.0166 (18) | −0.0044 (17) |
N2 | 0.073 (3) | 0.062 (3) | 0.097 (4) | −0.004 (2) | 0.004 (3) | −0.029 (3) |
C1 | 0.048 (2) | 0.048 (2) | 0.040 (2) | −0.0024 (18) | 0.0130 (18) | −0.0041 (17) |
C2 | 0.059 (3) | 0.055 (3) | 0.065 (3) | 0.003 (2) | 0.001 (2) | −0.017 (2) |
C3 | 0.069 (3) | 0.057 (3) | 0.067 (3) | −0.008 (2) | 0.010 (3) | −0.021 (2) |
C4 | 0.050 (3) | 0.072 (3) | 0.046 (2) | −0.016 (2) | 0.010 (2) | −0.003 (2) |
C5 | 0.049 (3) | 0.079 (4) | 0.064 (3) | 0.013 (2) | 0.005 (2) | −0.008 (3) |
C6 | 0.060 (3) | 0.068 (3) | 0.051 (3) | 0.009 (2) | 0.008 (2) | −0.017 (2) |
C7 | 0.049 (2) | 0.054 (2) | 0.039 (2) | 0.001 (2) | 0.0132 (18) | −0.0024 (19) |
C8 | 0.076 (3) | 0.042 (2) | 0.059 (3) | −0.001 (2) | 0.030 (3) | −0.003 (2) |
C9 | 0.094 (4) | 0.047 (3) | 0.059 (3) | 0.006 (3) | 0.033 (3) | −0.002 (2) |
C10 | 0.092 (4) | 0.062 (3) | 0.072 (3) | 0.029 (3) | 0.032 (3) | 0.011 (3) |
C11 | 0.078 (4) | 0.074 (4) | 0.070 (4) | 0.024 (3) | 0.008 (3) | 0.006 (3) |
C12 | 0.075 (3) | 0.059 (3) | 0.059 (3) | 0.015 (3) | 0.012 (3) | 0.000 (2) |
Geometric parameters (Å, º) top
Ag1—O2i | 2.207 (3) | C2—C3 | 1.373 (7) |
Ag1—O1 | 2.233 (4) | C2—H2 | 0.9301 |
Ag1—N1 | 2.352 (3) | C3—C4 | 1.362 (7) |
Ag1—Ag1i | 2.8913 (17) | C3—H3 | 0.9300 |
Cl1—C4 | 1.743 (5) | C4—C5 | 1.366 (7) |
O1—C7 | 1.260 (5) | C5—C6 | 1.374 (7) |
O2—C7 | 1.241 (5) | C5—H5 | 0.9300 |
O2—Ag1i | 2.207 (3) | C6—H6 | 0.9300 |
O1W—H1W | 0.8812 | C8—C9 | 1.405 (7) |
N1—C8 | 1.329 (6) | C9—C10 | 1.356 (8) |
N1—C12 | 1.352 (6) | C9—H9 | 0.9300 |
N2—C8 | 1.353 (7) | C10—C11 | 1.376 (9) |
N2—H2A | 0.8964 | C10—H10 | 0.9299 |
N2—H2B | 0.8938 | C11—C12 | 1.359 (7) |
C1—C6 | 1.375 (6) | C11—H11 | 0.9299 |
C1—C2 | 1.387 (6) | C12—H12 | 0.9300 |
C1—C7 | 1.499 (6) | | |
| | | |
O2i—Ag1—O1 | 162.59 (12) | C5—C4—Cl1 | 119.5 (4) |
O2i—Ag1—N1 | 95.17 (13) | C4—C5—C6 | 119.2 (5) |
O1—Ag1—N1 | 102.05 (13) | C4—C5—H5 | 120.4 |
O2i—Ag1—Ag1i | 79.08 (9) | C6—C5—H5 | 120.4 |
O1—Ag1—Ag1i | 83.55 (8) | C5—C6—C1 | 121.3 (4) |
N1—Ag1—Ag1i | 172.77 (10) | C5—C6—H6 | 119.3 |
C7—O1—Ag1 | 122.0 (3) | C1—C6—H6 | 119.4 |
C7—O2—Ag1i | 129.6 (3) | O2—C7—O1 | 125.5 (4) |
C8—N1—C12 | 118.4 (4) | O2—C7—C1 | 117.3 (4) |
C8—N1—Ag1 | 125.8 (3) | O1—C7—C1 | 117.1 (4) |
C12—N1—Ag1 | 115.7 (3) | N1—C8—N2 | 117.6 (4) |
C8—N2—H2A | 124.0 | N1—C8—C9 | 121.4 (5) |
C8—N2—H2B | 126.6 | N2—C8—C9 | 120.9 (5) |
H2A—N2—H2B | 104.9 | C10—C9—C8 | 118.4 (5) |
C6—C1—C2 | 118.1 (4) | C10—C9—H9 | 120.8 |
C6—C1—C7 | 120.3 (4) | C8—C9—H9 | 120.8 |
C2—C1—C7 | 121.6 (4) | C9—C10—C11 | 120.7 (5) |
C3—C2—C1 | 120.9 (5) | C9—C10—H10 | 119.6 |
C3—C2—H2 | 119.6 | C11—C10—H10 | 119.6 |
C1—C2—H2 | 119.6 | C12—C11—C10 | 117.9 (6) |
C4—C3—C2 | 119.5 (5) | C12—C11—H11 | 121.1 |
C4—C3—H3 | 120.2 | C10—C11—H11 | 121.1 |
C2—C3—H3 | 120.2 | N1—C12—C11 | 123.2 (5) |
C3—C4—C5 | 121.0 (5) | N1—C12—H12 | 118.4 |
C3—C4—Cl1 | 119.5 (4) | C11—C12—H12 | 118.4 |
| | | |
O2i—Ag1—O1—C7 | −8.1 (7) | Ag1i—O2—C7—C1 | 176.3 (3) |
N1—Ag1—O1—C7 | −179.5 (4) | Ag1—O1—C7—O2 | 6.5 (7) |
Ag1i—Ag1—O1—C7 | −4.1 (4) | Ag1—O1—C7—C1 | −174.8 (3) |
O2i—Ag1—N1—C8 | 172.9 (4) | C6—C1—C7—O2 | 3.1 (6) |
O1—Ag1—N1—C8 | −9.7 (4) | C2—C1—C7—O2 | −177.5 (5) |
O2i—Ag1—N1—C12 | −3.7 (4) | C6—C1—C7—O1 | −175.6 (4) |
O1—Ag1—N1—C12 | 173.7 (3) | C2—C1—C7—O1 | 3.7 (7) |
C6—C1—C2—C3 | 0.5 (8) | C12—N1—C8—N2 | −176.6 (5) |
C7—C1—C2—C3 | −178.8 (5) | Ag1—N1—C8—N2 | 6.8 (6) |
C1—C2—C3—C4 | −0.5 (8) | C12—N1—C8—C9 | 1.7 (7) |
C2—C3—C4—C5 | 0.2 (8) | Ag1—N1—C8—C9 | −174.9 (3) |
C2—C3—C4—Cl1 | 179.2 (4) | N1—C8—C9—C10 | −1.3 (7) |
C3—C4—C5—C6 | 0.1 (8) | N2—C8—C9—C10 | 177.0 (5) |
Cl1—C4—C5—C6 | −178.9 (4) | C8—C9—C10—C11 | 0.1 (8) |
C4—C5—C6—C1 | −0.1 (8) | C9—C10—C11—C12 | 0.5 (9) |
C2—C1—C6—C5 | −0.2 (8) | C8—N1—C12—C11 | −1.0 (8) |
C7—C1—C6—C5 | 179.1 (5) | Ag1—N1—C12—C11 | 175.9 (5) |
Ag1i—O2—C7—O1 | −5.1 (7) | C10—C11—C12—N1 | −0.1 (9) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1Wii | 0.90 | 2.17 | 3.037 (6) | 162 |
N2—H2B···O1 | 0.89 | 2.17 | 3.009 (6) | 156 |
O1W—H1W···O1 | 0.88 | 2.09 | 2.892 (4) | 151 |
Symmetry code: (ii) x, y−1, z. |