Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004756/ci6199sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004756/ci6199Isup2.hkl |
CCDC reference: 209879
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.040
- wR factor = 0.114
- Data-to-parameter ratio = 15.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 43.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
At ambient temperature, an alcohol solution (5 ml) of diethylenetriamine (103 mg, 1 mmol) was added to 2-fluorobenzaldehyde (248 mg, 2 mmol) in alcohol (10 ml) with stirring. After half an hour, AgNO3 (170 mg, 1 mmol) in acetonitrile (5 ml) was added to the above solution. The resultant solution was kept in air to evaporate slowly. Colorless single crystals of the title complex, (I), were deposited and were collected by filtration. The crystals were washed with a mixture of alcohol and acetonitrile (1:1 v/v) and then dried in a vacuum desiccator over silica gel (yield 81%). Analysis calculated for (I), C32H26AgF4N4+·NO3-: C 53.95, H 3.68, N 9.83, F 10.67%; found: C 54.40, H 3.88, N 9.69, F 10.89%. IR spectra; 3010 (w), 1638 (m), 1610 (m), 1485 (m), 1452 (m), 1360 (w), 1347 (s), 1301 (m), 1282 (w), 1234 (m), 1198 (w), 1193 (w), 1101 (w), 1041 (w), 970 (w), 831 (w), 781 (w), 776 (m), 757 (s).
Atoms C8 and C9 of the ethylenediamine group were found to be disordered. The occupancies of the disordered positions C8A/C8B and C9A/C9B were refined to 0.55 (1)/0.45 (1). The corresponding N—C and C—C distances in the major and minor conformers were restrained to be equal. The N atom of the NO3- anion lies on a twofold axis and hence there are two positions for each O atom, related by the symmetry operation (1 - x, y, 1/2 - z), with equal occupancies. Significant deviation in the N—O bond lengths were observed and attempts to restrain them resulted in an unstable refinement. The H atoms were geometrically positioned and were treated as riding atoms on the parent C atoms, with C—H distances of 0.93 or 0.97 Å.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
[Ag(C16H14F2N2)2]NO3 | F(000) = 1448 |
Mr = 714.46 | Dx = 1.564 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4783 reflections |
a = 13.0142 (15) Å | θ = 2.8–28.3° |
b = 18.102 (2) Å | µ = 0.73 mm−1 |
c = 14.1367 (17) Å | T = 293 K |
β = 114.328 (2)° | Block, light yellow |
V = 3034.6 (6) Å3 | 0.46 × 0.36 × 0.32 mm |
Z = 4 |
Siemens SMART CCD area-detector diffractometer | 3699 independent reflections |
Radiation source: fine-focus sealed tube | 2832 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.8° |
ω scans | h = −17→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −23→17 |
Tmin = 0.730, Tmax = 0.800 | l = −18→18 |
9317 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0551P)2 + 2.0621P] where P = (Fo2 + 2Fc2)/3 |
3699 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.71 e Å−3 |
7 restraints | Δρmin = −0.46 e Å−3 |
[Ag(C16H14F2N2)2]NO3 | V = 3034.6 (6) Å3 |
Mr = 714.46 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.0142 (15) Å | µ = 0.73 mm−1 |
b = 18.102 (2) Å | T = 293 K |
c = 14.1367 (17) Å | 0.46 × 0.36 × 0.32 mm |
β = 114.328 (2)° |
Siemens SMART CCD area-detector diffractometer | 3699 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2832 reflections with I > 2σ(I) |
Tmin = 0.730, Tmax = 0.800 | Rint = 0.022 |
9317 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 7 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.71 e Å−3 |
3699 reflections | Δρmin = −0.46 e Å−3 |
237 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.5000 | 0.128685 (17) | 0.2500 | 0.06565 (15) | |
N1 | 0.3355 (2) | 0.18904 (18) | 0.2193 (3) | 0.0980 (11) | |
N2 | 0.4202 (2) | 0.06010 (15) | 0.34250 (19) | 0.0669 (6) | |
F1 | 0.3222 (2) | 0.40612 (16) | 0.2132 (2) | 0.1119 (8) | |
F2 | 0.4300 (2) | −0.15841 (14) | 0.3706 (2) | 0.1054 (7) | |
C1 | 0.3644 (3) | 0.37560 (18) | 0.1489 (3) | 0.0719 (8) | |
C2 | 0.4100 (3) | 0.4209 (2) | 0.0990 (3) | 0.0844 (10) | |
H2 | 0.4126 | 0.4718 | 0.1092 | 0.101* | |
C3 | 0.4516 (3) | 0.3903 (2) | 0.0340 (3) | 0.0879 (11) | |
H3 | 0.4829 | 0.4202 | −0.0007 | 0.106* | |
C4 | 0.4474 (3) | 0.3151 (2) | 0.0198 (3) | 0.0815 (9) | |
H4 | 0.4752 | 0.2945 | −0.0253 | 0.098* | |
C5 | 0.4030 (3) | 0.27021 (18) | 0.0711 (2) | 0.0694 (8) | |
H5 | 0.4017 | 0.2194 | 0.0613 | 0.083* | |
C6 | 0.3596 (2) | 0.29996 (18) | 0.1381 (2) | 0.0631 (7) | |
C7 | 0.3077 (3) | 0.2547 (2) | 0.1921 (3) | 0.0902 (12) | |
H7 | 0.2510 | 0.2757 | 0.2073 | 0.108* | |
C8A | 0.2560 (4) | 0.1353 (3) | 0.2388 (5) | 0.064 (2) | 0.547 (12) |
H8AA | 0.1886 | 0.1601 | 0.2355 | 0.077* | 0.547 (12) |
H8AB | 0.2345 | 0.0950 | 0.1891 | 0.077* | 0.547 (12) |
C9A | 0.3265 (6) | 0.1084 (6) | 0.3462 (5) | 0.069 (3) | 0.547 (12) |
H9AA | 0.2804 | 0.0802 | 0.3724 | 0.083* | 0.547 (12) |
H9AB | 0.3585 | 0.1500 | 0.3922 | 0.083* | 0.547 (12) |
C8B | 0.3011 (8) | 0.1673 (4) | 0.3078 (7) | 0.084 (3) | 0.453 (12) |
H8BA | 0.3555 | 0.1859 | 0.3739 | 0.101* | 0.453 (12) |
H8BB | 0.2274 | 0.1874 | 0.2953 | 0.101* | 0.453 (12) |
C9B | 0.2984 (5) | 0.0847 (4) | 0.3083 (12) | 0.080 (4) | 0.453 (12) |
H9BA | 0.2521 | 0.0659 | 0.2396 | 0.096* | 0.453 (12) |
H9BB | 0.2681 | 0.0669 | 0.3564 | 0.096* | 0.453 (12) |
C10 | 0.4332 (2) | −0.00612 (19) | 0.3713 (2) | 0.0657 (7) | |
H10 | 0.3767 | −0.0286 | 0.3853 | 0.079* | |
C11 | 0.5328 (2) | −0.04975 (16) | 0.38402 (19) | 0.0577 (6) | |
C12 | 0.6366 (2) | −0.01855 (18) | 0.3989 (2) | 0.0651 (7) | |
H12 | 0.6444 | 0.0326 | 0.4014 | 0.078* | |
C13 | 0.7268 (3) | −0.0617 (2) | 0.4100 (3) | 0.0814 (9) | |
H13 | 0.7952 | −0.0397 | 0.4204 | 0.098* | |
C14 | 0.7173 (4) | −0.1373 (2) | 0.4058 (3) | 0.0869 (11) | |
H14 | 0.7792 | −0.1662 | 0.4128 | 0.104* | |
C15 | 0.6177 (3) | −0.1703 (2) | 0.3915 (3) | 0.0821 (10) | |
H15 | 0.6105 | −0.2214 | 0.3880 | 0.099* | |
C16 | 0.5289 (3) | −0.12610 (18) | 0.3824 (2) | 0.0696 (8) | |
N3 | 0.5000 | 0.6238 (2) | 0.2500 | 0.0816 (13) | |
O1 | 0.4437 (10) | 0.6235 (5) | 0.1510 (8) | 0.131 (3) | 0.50 |
O2 | 0.4918 (17) | 0.5708 (5) | 0.2910 (11) | 0.223 (7) | 0.50 |
O3 | 0.5121 (13) | 0.6788 (5) | 0.2925 (9) | 0.176 (6) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0617 (2) | 0.0581 (2) | 0.0970 (3) | 0.000 | 0.05276 (19) | 0.000 |
N1 | 0.0704 (17) | 0.098 (2) | 0.152 (3) | 0.0307 (16) | 0.0726 (19) | 0.059 (2) |
N2 | 0.0660 (14) | 0.0853 (17) | 0.0639 (14) | 0.0110 (12) | 0.0413 (12) | 0.0185 (13) |
F1 | 0.1139 (18) | 0.1102 (18) | 0.1184 (18) | 0.0285 (15) | 0.0548 (15) | −0.0149 (15) |
F2 | 0.0967 (16) | 0.0912 (14) | 0.1305 (19) | −0.0269 (13) | 0.0491 (14) | 0.0124 (14) |
C1 | 0.0608 (17) | 0.076 (2) | 0.0694 (18) | 0.0178 (15) | 0.0175 (14) | 0.0011 (16) |
C2 | 0.082 (2) | 0.0641 (19) | 0.099 (3) | 0.0027 (17) | 0.028 (2) | 0.0035 (18) |
C3 | 0.082 (2) | 0.084 (2) | 0.095 (3) | −0.0050 (19) | 0.033 (2) | 0.020 (2) |
C4 | 0.089 (2) | 0.088 (2) | 0.074 (2) | 0.0059 (19) | 0.0400 (18) | 0.0051 (18) |
C5 | 0.0725 (18) | 0.0648 (17) | 0.0718 (18) | 0.0055 (14) | 0.0304 (15) | 0.0011 (14) |
C6 | 0.0510 (14) | 0.0711 (18) | 0.0632 (16) | 0.0142 (13) | 0.0194 (12) | 0.0093 (14) |
C7 | 0.071 (2) | 0.102 (3) | 0.117 (3) | 0.0379 (19) | 0.059 (2) | 0.043 (2) |
C8A | 0.050 (3) | 0.085 (4) | 0.064 (4) | −0.003 (3) | 0.031 (3) | 0.002 (3) |
C9A | 0.062 (4) | 0.104 (8) | 0.058 (4) | 0.010 (4) | 0.041 (3) | 0.013 (4) |
C8B | 0.078 (5) | 0.078 (5) | 0.126 (9) | 0.016 (4) | 0.072 (6) | 0.022 (5) |
C9B | 0.086 (7) | 0.071 (6) | 0.110 (11) | 0.004 (5) | 0.068 (7) | 0.014 (6) |
C10 | 0.0622 (16) | 0.087 (2) | 0.0550 (15) | −0.0059 (14) | 0.0316 (13) | 0.0160 (14) |
C11 | 0.0612 (15) | 0.0695 (17) | 0.0411 (12) | −0.0051 (12) | 0.0199 (11) | 0.0068 (12) |
C12 | 0.0614 (16) | 0.0712 (18) | 0.0601 (16) | −0.0054 (14) | 0.0223 (13) | 0.0052 (14) |
C13 | 0.0628 (18) | 0.098 (3) | 0.082 (2) | 0.0006 (18) | 0.0277 (16) | 0.0058 (19) |
C14 | 0.089 (3) | 0.091 (3) | 0.087 (2) | 0.017 (2) | 0.043 (2) | 0.0075 (19) |
C15 | 0.105 (3) | 0.067 (2) | 0.079 (2) | 0.0049 (19) | 0.043 (2) | 0.0025 (16) |
C16 | 0.0755 (19) | 0.076 (2) | 0.0573 (16) | −0.0148 (16) | 0.0274 (14) | 0.0052 (14) |
N3 | 0.073 (2) | 0.055 (3) | 0.132 (5) | 0.000 | 0.058 (3) | 0.000 |
O1 | 0.165 (8) | 0.140 (9) | 0.106 (6) | −0.029 (6) | 0.076 (6) | −0.013 (5) |
O2 | 0.343 (17) | 0.106 (6) | 0.25 (2) | 0.069 (10) | 0.155 (17) | 0.074 (9) |
O3 | 0.229 (12) | 0.122 (6) | 0.227 (17) | −0.060 (9) | 0.145 (15) | −0.079 (8) |
Ag1—N1i | 2.280 (3) | C8A—H8AB | 0.97 |
Ag1—N1 | 2.280 (3) | C9A—H9AA | 0.97 |
Ag1—N2i | 2.334 (2) | C9A—H9AB | 0.97 |
Ag1—N2 | 2.334 (2) | C8B—C9B | 1.497 (7) |
N1—C7 | 1.256 (4) | C8B—H8BA | 0.97 |
N1—C8A | 1.526 (4) | C8B—H8BB | 0.97 |
N1—C8B | 1.544 (5) | C9B—H9BA | 0.97 |
N2—C10 | 1.255 (4) | C9B—H9BB | 0.97 |
N2—C9A | 1.518 (4) | C10—C11 | 1.465 (4) |
N2—C9B | 1.521 (5) | C10—H10 | 0.93 |
F1—C1 | 1.357 (4) | C11—C16 | 1.383 (4) |
F2—C16 | 1.360 (4) | C11—C12 | 1.398 (4) |
C1—C2 | 1.368 (5) | C12—C13 | 1.364 (5) |
C1—C6 | 1.376 (4) | C12—H12 | 0.93 |
C2—C3 | 1.362 (6) | C13—C14 | 1.373 (5) |
C2—H2 | 0.93 | C13—H13 | 0.93 |
C3—C4 | 1.373 (5) | C14—C15 | 1.364 (6) |
C3—H3 | 0.93 | C14—H14 | 0.93 |
C4—C5 | 1.366 (5) | C15—C16 | 1.368 (5) |
C4—H4 | 0.93 | C15—H15 | 0.93 |
C5—C6 | 1.396 (4) | N3—O3 | 1.140 (8) |
C5—H5 | 0.93 | N3—O3i | 1.140 (8) |
C6—C7 | 1.461 (5) | N3—O2 | 1.148 (10) |
C7—H7 | 0.93 | N3—O2i | 1.148 (10) |
C8A—C9A | 1.495 (7) | N3—O1i | 1.285 (10) |
C8A—H8AA | 0.97 | N3—O1 | 1.285 (10) |
N1i—Ag1—N1 | 122.7 (2) | C8A—C9A—H9AA | 110.0 |
N1i—Ag1—N2i | 76.24 (9) | N2—C9A—H9AA | 110.0 |
N1—Ag1—N2i | 138.38 (12) | C8A—C9A—H9AB | 110.0 |
N1i—Ag1—N2 | 138.38 (12) | N2—C9A—H9AB | 110.0 |
N1—Ag1—N2 | 76.24 (9) | H9AA—C9A—H9AB | 108.4 |
N2i—Ag1—N2 | 115.74 (13) | C9B—C8B—N1 | 105.8 (8) |
C7—N1—C8A | 121.8 (3) | C9B—C8B—H8BA | 110.6 |
C7—N1—C8B | 110.2 (4) | N1—C8B—H8BA | 110.6 |
C7—N1—Ag1 | 129.9 (2) | C9B—C8B—H8BB | 110.6 |
C8A—N1—Ag1 | 108.3 (3) | N1—C8B—H8BB | 110.6 |
C8B—N1—Ag1 | 106.7 (3) | H8BA—C8B—H8BB | 108.7 |
C10—N2—C9A | 122.8 (5) | C8B—C9B—N2 | 105.7 (5) |
C10—N2—C9B | 111.5 (4) | C8B—C9B—H9BA | 110.6 |
C10—N2—Ag1 | 131.2 (2) | N2—C9B—H9BA | 110.6 |
C9A—N2—Ag1 | 105.2 (4) | C8B—C9B—H9BB | 110.6 |
C9B—N2—Ag1 | 108.2 (5) | N2—C9B—H9BB | 110.6 |
F1—C1—C2 | 118.9 (3) | H9BA—C9B—H9BB | 108.7 |
F1—C1—C6 | 117.9 (3) | N2—C10—C11 | 123.3 (3) |
C2—C1—C6 | 123.3 (3) | N2—C10—H10 | 118.4 |
C3—C2—C1 | 118.8 (3) | C11—C10—H10 | 118.4 |
C3—C2—H2 | 120.6 | C16—C11—C12 | 115.6 (3) |
C1—C2—H2 | 120.6 | C16—C11—C10 | 120.8 (3) |
C2—C3—C4 | 120.0 (4) | C12—C11—C10 | 123.5 (3) |
C2—C3—H3 | 120.0 | C13—C12—C11 | 121.2 (3) |
C4—C3—H3 | 120.0 | C13—C12—H12 | 119.4 |
C5—C4—C3 | 120.8 (4) | C11—C12—H12 | 119.4 |
C5—C4—H4 | 119.6 | C12—C13—C14 | 120.6 (4) |
C3—C4—H4 | 119.6 | C12—C13—H13 | 119.7 |
C4—C5—C6 | 120.6 (3) | C14—C13—H13 | 119.7 |
C4—C5—H5 | 119.7 | C15—C14—C13 | 120.4 (4) |
C6—C5—H5 | 119.7 | C15—C14—H14 | 119.8 |
C1—C6—C5 | 116.5 (3) | C13—C14—H14 | 119.8 |
C1—C6—C7 | 120.6 (3) | C14—C15—C16 | 118.2 (3) |
C5—C6—C7 | 122.8 (3) | C14—C15—H15 | 120.9 |
N1—C7—C6 | 123.6 (3) | C16—C15—H15 | 120.9 |
N1—C7—H7 | 118.2 | F2—C16—C15 | 118.7 (3) |
C6—C7—H7 | 118.2 | F2—C16—C11 | 117.3 (3) |
C9A—C8A—N1 | 102.3 (6) | C15—C16—C11 | 124.0 (3) |
C9A—C8A—H8AA | 111.3 | O3—N3—O2 | 119.1 (9) |
N1—C8A—H8AA | 111.3 | O3—N3—O1 | 118.1 (11) |
C9A—C8A—H8AB | 111.3 | O2—N3—O1 | 114.6 (12) |
N1—C8A—H8AB | 111.3 | O3i—N3—O2i | 119.1 (9) |
H8AA—C8A—H8AB | 109.2 | O3i—N3—O1i | 118.1 (11) |
C8A—C9A—N2 | 108.6 (4) | O2i—N3—O1i | 114.6 (12) |
N1i—Ag1—N1—C7 | 18.3 (4) | Ag1—N1—C7—C6 | 23.4 (7) |
N2i—Ag1—N1—C7 | −89.0 (5) | C1—C6—C7—N1 | −151.8 (4) |
N2—Ag1—N1—C7 | 157.5 (5) | C5—C6—C7—N1 | 30.3 (6) |
N1i—Ag1—N1—C8A | −160.9 (3) | C7—N1—C8A—C9A | −125.8 (5) |
N2i—Ag1—N1—C8A | 91.7 (3) | Ag1—N1—C8A—C9A | 53.5 (5) |
N2—Ag1—N1—C8A | −21.7 (3) | N1—C8A—C9A—N2 | −69.7 (8) |
N1i—Ag1—N1—C8B | −117.8 (4) | C10—N2—C9A—C8A | −121.2 (7) |
N2i—Ag1—N1—C8B | 134.9 (4) | C9B—N2—C9A—C8A | −51.3 (14) |
N2—Ag1—N1—C8B | 21.5 (4) | Ag1—N2—C9A—C8A | 49.3 (8) |
N1i—Ag1—N2—C10 | −80.0 (3) | C7—N1—C8B—C9B | 160.2 (6) |
N1—Ag1—N2—C10 | 155.7 (3) | Ag1—N1—C8B—C9B | −54.4 (7) |
N2i—Ag1—N2—C10 | 18.3 (3) | N1—C8B—C9B—N2 | 67.5 (11) |
N1i—Ag1—N2—C9A | 110.6 (4) | C10—N2—C9B—C8B | 163.1 (7) |
N1—Ag1—N2—C9A | −13.6 (4) | C9A—N2—C9B—C8B | 41.1 (11) |
N2i—Ag1—N2—C9A | −151.0 (4) | Ag1—N2—C9B—C8B | −46.0 (11) |
N1i—Ag1—N2—C9B | 136.9 (5) | C9A—N2—C10—C11 | −169.9 (4) |
N1—Ag1—N2—C9B | 12.6 (5) | C9B—N2—C10—C11 | 164.6 (7) |
N2i—Ag1—N2—C9B | −124.8 (5) | Ag1—N2—C10—C11 | 22.4 (5) |
F1—C1—C2—C3 | −179.6 (3) | N2—C10—C11—C16 | −158.7 (3) |
C6—C1—C2—C3 | 0.9 (5) | N2—C10—C11—C12 | 21.6 (4) |
C1—C2—C3—C4 | −0.1 (6) | C16—C11—C12—C13 | 0.6 (4) |
C2—C3—C4—C5 | −0.7 (6) | C10—C11—C12—C13 | −179.7 (3) |
C3—C4—C5—C6 | 0.8 (5) | C11—C12—C13—C14 | 0.5 (5) |
F1—C1—C6—C5 | 179.7 (3) | C12—C13—C14—C15 | −0.6 (6) |
C2—C1—C6—C5 | −0.8 (5) | C13—C14—C15—C16 | −0.6 (6) |
F1—C1—C6—C7 | 1.7 (4) | C14—C15—C16—F2 | −178.4 (3) |
C2—C1—C6—C7 | −178.8 (3) | C14—C15—C16—C11 | 1.8 (5) |
C4—C5—C6—C1 | −0.1 (4) | C12—C11—C16—F2 | 178.4 (3) |
C4—C5—C6—C7 | 177.9 (3) | C10—C11—C16—F2 | −1.2 (4) |
C8A—N1—C7—C6 | −157.5 (4) | C12—C11—C16—C15 | −1.8 (5) |
C8B—N1—C7—C6 | 158.3 (5) | C10—C11—C16—C15 | 178.5 (3) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C16H14F2N2)2]NO3 |
Mr | 714.46 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.0142 (15), 18.102 (2), 14.1367 (17) |
β (°) | 114.328 (2) |
V (Å3) | 3034.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.73 |
Crystal size (mm) | 0.46 × 0.36 × 0.32 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.730, 0.800 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9317, 3699, 2832 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.114, 1.09 |
No. of reflections | 3699 |
No. of parameters | 237 |
No. of restraints | 7 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.71, −0.46 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Ag1—N1 | 2.280 (3) | N1—C7 | 1.256 (4) |
Ag1—N2 | 2.334 (2) | N2—C10 | 1.255 (4) |
N1i—Ag1—N1 | 122.7 (2) | N1—Ag1—N2 | 76.24 (9) |
N1i—Ag1—N2 | 138.38 (12) | N2i—Ag1—N2 | 115.74 (13) |
Symmetry code: (i) −x+1, y, −z+1/2. |
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The propensity for d10Ag+ cations to form coordination complexes with a variety of ligands, such as those containing N, O and S donors, has been widely studied (Buchholz et al., 1996; Amoroso et al., 1995; Michaelides et al., 1995). However, the isolation of silver(I) complexes is complicated by the fact that they often form polynuclear complexes. Moreover, from a practical viewpoint, there are serious problems, namely, nearly all polymeric silver(I) complexes are water insoluble and most of them are unstable upon exposure to light. In this work, a new organic bis-Schiff base ligand was utilized to ligate with silver(I) ions, to form a water soluble and stable complex, (I).
The title compound is an ionic complex of a bis[N,N'-bis(2-fluorobenzylidene)ethylenediamine]silver(I) cation and a nitrate anion. The asymmetric unit consists of one half of the cation and one half of the anion with the other halves generated by a crystallographic twofold axis. Atoms Ag1 and N3 lie on the twofold axis. The AgI atom is four-coordinated by two N atoms from each of the two symmetry-related bidentate N,N'-bis(2-fluorobenzylidene)ethylenediamine ligands. This AgN4 coordination forms a heavily distorted tetrahedral geometry, with bond angles around the Ag atom deviating significantly from ideal values (Table 1). The Ag—N bond lengths in (I) are slightly shorter compared with the mean value of 2.403 Å reported by Orpen et al. (1989), for such distances in the coordination complexes of Schiff bases.