Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057546/lh2554sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057546/lh2554Isup2.hkl |
CCDC reference: 672678
A water (8 ml) solution containing AgNO3 (17.3 mg, 0.1 mmol), 4-bpo (11.2 mg, 0.05 mmol), and oxamide (9.0 mg, 0.1 mmol) was sealed in a Teflon-lined stainless steel vessel (20 ml), which was heated to 373 K for 24 h and subsequently cooled to room temperature at a rate of 1 K/h. Colorless block shape crystals were obtained in 75% yield (11.9 mg, based on 4-bpo). IR (cm-1): 3385b, 2362s, 1654s, 1563m, 1536m, 1484m, 1416m, 1384vs, 1106m, 988w, 832m, 741w, 713s, 637w.
C-bound hydrogen atoms were placed geometrically C—H = 0.93 Å and refined as riding with Uiso(H) = 1.2Ueq(C). Hydrogen atoms bonded to the water O atom were visible in difference Fourier maps, but were fixed geometrically with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 (Bruker, 2003) and SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2001).
[Ag(C12H8N4O)2]NO3·H2O | F(000) = 1280 |
Mr = 636.34 | Dx = 1.741 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4561 reflections |
a = 7.3200 (19) Å | θ = 2.2–25.8° |
b = 13.281 (3) Å | µ = 0.89 mm−1 |
c = 25.002 (6) Å | T = 294 K |
β = 92.664 (3)° | Block, colourless |
V = 2428.0 (11) Å3 | 0.14 × 0.13 × 0.09 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 4287 independent reflections |
Radiation source: fine-focus sealed tube | 3232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→7 |
Tmin = 0.781, Tmax = 0.849 | k = −15→15 |
13051 measured reflections | l = −29→29 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0405P)2 + 1.1166P] where P = (Fo2 + 2Fc2)/3 |
4287 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Ag(C12H8N4O)2]NO3·H2O | V = 2428.0 (11) Å3 |
Mr = 636.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.3200 (19) Å | µ = 0.89 mm−1 |
b = 13.281 (3) Å | T = 294 K |
c = 25.002 (6) Å | 0.14 × 0.13 × 0.09 mm |
β = 92.664 (3)° |
Bruker APEXII CCD diffractometer | 4287 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3232 reflections with I > 2σ(I) |
Tmin = 0.781, Tmax = 0.849 | Rint = 0.021 |
13051 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.50 e Å−3 |
4287 reflections | Δρmin = −0.39 e Å−3 |
361 parameters |
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 | ||
Ag1 | 0.75772 (4) | 0.494095 (15) | 0.003989 (9) | 0.06022 (12) | |
O1 | 0.7828 (2) | 0.01648 (12) | 0.14056 (6) | 0.0331 (4) | |
O2 | 0.7228 (2) | 0.96348 (13) | −0.13712 (6) | 0.0353 (4) | |
O3 | 0.3960 (5) | 0.5442 (2) | 0.15393 (12) | 0.0977 (9) | |
O4 | 0.6848 (4) | 0.5320 (2) | 0.14858 (12) | 0.0962 (9) | |
O5 | 0.5187 (5) | 0.5726 (2) | 0.07974 (11) | 0.1103 (11) | |
N1 | 0.7338 (3) | 0.34138 (15) | 0.03382 (8) | 0.0400 (5) | |
N2 | 0.6208 (3) | −0.03195 (16) | 0.06841 (8) | 0.0390 (5) | |
N3 | 0.6508 (3) | −0.11581 (15) | 0.10182 (8) | 0.0394 (5) | |
N4 | 0.9379 (4) | −0.26272 (19) | 0.27527 (9) | 0.0542 (6) | |
N5 | 0.7790 (3) | 0.64634 (16) | −0.02698 (9) | 0.0422 (5) | |
N6 | 0.8743 (3) | 1.02181 (15) | −0.06527 (8) | 0.0385 (5) | |
N7 | 0.8432 (3) | 1.10181 (16) | −0.10126 (8) | 0.0403 (5) | |
N8 | 0.5575 (4) | 1.2125 (2) | −0.28380 (10) | 0.0635 (8) | |
N9 | 0.5326 (5) | 0.55187 (18) | 0.12635 (12) | 0.0624 (8) | |
C1 | 0.7127 (3) | 0.14629 (17) | 0.07331 (9) | 0.0294 (5) | |
C2 | 0.7864 (3) | 0.22346 (18) | 0.10502 (9) | 0.0351 (6) | |
H2 | 0.8297 | 0.2108 | 0.1399 | 0.042* | |
C3 | 0.7942 (4) | 0.31880 (19) | 0.08386 (10) | 0.0402 (6) | |
H3 | 0.8437 | 0.3701 | 0.1053 | 0.048* | |
C4 | 0.6629 (4) | 0.26646 (19) | 0.00361 (10) | 0.0391 (6) | |
H4 | 0.6216 | 0.2810 | −0.0313 | 0.047* | |
C5 | 0.6482 (4) | 0.16930 (18) | 0.02156 (9) | 0.0354 (6) | |
H5 | 0.5960 | 0.1197 | −0.0005 | 0.042* | |
C6 | 0.7006 (3) | 0.04297 (18) | 0.09256 (9) | 0.0315 (6) | |
C7 | 0.7458 (3) | −0.08427 (18) | 0.14297 (10) | 0.0331 (6) | |
C8 | 0.8143 (4) | −0.14296 (19) | 0.18910 (10) | 0.0359 (6) | |
C9 | 0.8063 (4) | −0.2469 (2) | 0.18619 (11) | 0.0457 (7) | |
H9 | 0.7597 | −0.2788 | 0.1554 | 0.055* | |
C10 | 0.8688 (4) | −0.3024 (2) | 0.22991 (12) | 0.0535 (8) | |
H10 | 0.8621 | −0.3722 | 0.2275 | 0.064* | |
C11 | 0.9429 (4) | −0.1626 (2) | 0.27713 (11) | 0.0508 (8) | |
H11 | 0.9894 | −0.1329 | 0.3086 | 0.061* | |
C12 | 0.8842 (4) | −0.0996 (2) | 0.23588 (10) | 0.0426 (7) | |
H12 | 0.8917 | −0.0300 | 0.2395 | 0.051* | |
C13 | 0.7920 (3) | 0.84052 (18) | −0.06722 (9) | 0.0319 (6) | |
C14 | 0.7207 (4) | 0.76235 (19) | −0.09872 (10) | 0.0378 (6) | |
H14 | 0.6758 | 0.7742 | −0.1336 | 0.045* | |
C15 | 0.7181 (4) | 0.66720 (19) | −0.07716 (11) | 0.0430 (7) | |
H15 | 0.6719 | 0.6148 | −0.0984 | 0.052* | |
C16 | 0.8458 (4) | 0.72245 (19) | 0.00307 (10) | 0.0399 (6) | |
H16 | 0.8871 | 0.7089 | 0.0381 | 0.048* | |
C17 | 0.8562 (4) | 0.81970 (18) | −0.01540 (9) | 0.0363 (6) | |
H17 | 0.9053 | 0.8705 | 0.0065 | 0.044* | |
C18 | 0.8010 (3) | 0.94280 (18) | −0.08788 (9) | 0.0324 (6) | |
C19 | 0.7541 (4) | 1.06397 (18) | −0.14211 (10) | 0.0348 (6) | |
C20 | 0.6850 (4) | 1.1144 (2) | −0.19096 (10) | 0.0379 (6) | |
C21 | 0.6799 (4) | 1.2186 (2) | −0.19361 (11) | 0.0467 (7) | |
H21 | 0.7187 | 1.2576 | −0.1643 | 0.056* | |
C22 | 0.6162 (5) | 1.2629 (3) | −0.24038 (13) | 0.0594 (8) | |
H22 | 0.6138 | 1.3328 | −0.2418 | 0.071* | |
C23 | 0.5636 (5) | 1.1129 (3) | −0.28027 (12) | 0.0640 (9) | |
H23 | 0.5237 | 1.0761 | −0.3102 | 0.077* | |
C24 | 0.6249 (4) | 1.0599 (2) | −0.23536 (11) | 0.0510 (7) | |
H24 | 0.6255 | 0.9899 | −0.2351 | 0.061* | |
O6 | 0.0299 (5) | 0.5615 (2) | 0.09432 (11) | 0.1088 (10) | |
H6A | −0.0340 | 0.5408 | 0.1197 | 0.163* | |
H6B | 0.1381 | 0.5810 | 0.1026 | 0.163* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0852 (2) | 0.03234 (14) | 0.06241 (18) | −0.00484 (12) | −0.00465 (14) | 0.01112 (10) |
O1 | 0.0375 (10) | 0.0287 (9) | 0.0324 (9) | −0.0012 (7) | −0.0035 (7) | 0.0006 (7) |
O2 | 0.0401 (11) | 0.0334 (9) | 0.0318 (9) | −0.0022 (8) | −0.0060 (8) | −0.0008 (7) |
O3 | 0.118 (3) | 0.0802 (19) | 0.096 (2) | 0.0038 (18) | 0.0234 (19) | −0.0079 (16) |
O4 | 0.106 (2) | 0.0663 (16) | 0.112 (2) | −0.0123 (16) | −0.0351 (19) | 0.0043 (15) |
O5 | 0.159 (3) | 0.108 (2) | 0.0636 (18) | 0.023 (2) | −0.0036 (18) | 0.0261 (16) |
N1 | 0.0477 (15) | 0.0320 (11) | 0.0396 (12) | −0.0005 (10) | −0.0035 (10) | 0.0025 (9) |
N2 | 0.0454 (14) | 0.0339 (11) | 0.0370 (12) | −0.0049 (10) | −0.0072 (10) | 0.0031 (9) |
N3 | 0.0457 (15) | 0.0327 (11) | 0.0392 (12) | −0.0059 (10) | −0.0039 (10) | 0.0039 (9) |
N4 | 0.0566 (17) | 0.0581 (16) | 0.0474 (14) | 0.0071 (13) | −0.0035 (12) | 0.0134 (12) |
N5 | 0.0515 (15) | 0.0339 (11) | 0.0409 (13) | −0.0007 (11) | −0.0010 (11) | 0.0034 (9) |
N6 | 0.0443 (14) | 0.0330 (11) | 0.0372 (12) | −0.0028 (10) | −0.0074 (10) | 0.0013 (9) |
N7 | 0.0482 (15) | 0.0330 (11) | 0.0389 (12) | −0.0030 (10) | −0.0073 (11) | 0.0021 (9) |
N8 | 0.0556 (18) | 0.086 (2) | 0.0479 (16) | 0.0098 (15) | −0.0030 (13) | 0.0239 (14) |
N9 | 0.088 (2) | 0.0349 (14) | 0.0635 (19) | −0.0041 (15) | −0.0099 (18) | −0.0045 (12) |
C1 | 0.0263 (14) | 0.0315 (12) | 0.0305 (13) | 0.0004 (10) | 0.0014 (10) | −0.0017 (9) |
C2 | 0.0388 (16) | 0.0366 (13) | 0.0294 (12) | 0.0001 (12) | −0.0038 (11) | −0.0026 (10) |
C3 | 0.0475 (18) | 0.0313 (13) | 0.0413 (15) | −0.0042 (12) | −0.0023 (12) | −0.0060 (11) |
C4 | 0.0459 (17) | 0.0374 (14) | 0.0335 (13) | 0.0001 (13) | −0.0045 (12) | 0.0025 (11) |
C5 | 0.0389 (16) | 0.0347 (13) | 0.0320 (13) | −0.0014 (11) | −0.0035 (11) | −0.0040 (10) |
C6 | 0.0307 (15) | 0.0353 (13) | 0.0282 (12) | −0.0004 (11) | −0.0001 (10) | −0.0012 (10) |
C7 | 0.0340 (15) | 0.0300 (13) | 0.0354 (13) | −0.0021 (11) | 0.0032 (11) | −0.0004 (10) |
C8 | 0.0343 (15) | 0.0387 (14) | 0.0347 (13) | 0.0006 (12) | 0.0013 (11) | 0.0054 (11) |
C9 | 0.0520 (19) | 0.0383 (14) | 0.0459 (16) | −0.0030 (13) | −0.0073 (13) | 0.0036 (12) |
C10 | 0.059 (2) | 0.0407 (15) | 0.0601 (19) | 0.0021 (15) | −0.0047 (16) | 0.0110 (14) |
C11 | 0.055 (2) | 0.062 (2) | 0.0354 (15) | 0.0054 (16) | −0.0038 (13) | 0.0010 (13) |
C12 | 0.0473 (18) | 0.0419 (15) | 0.0384 (15) | 0.0025 (13) | −0.0013 (13) | 0.0002 (11) |
C13 | 0.0296 (15) | 0.0342 (13) | 0.0319 (13) | 0.0024 (11) | 0.0006 (11) | −0.0002 (10) |
C14 | 0.0420 (17) | 0.0382 (14) | 0.0325 (13) | −0.0034 (12) | −0.0051 (12) | −0.0018 (10) |
C15 | 0.0513 (18) | 0.0340 (14) | 0.0431 (15) | −0.0065 (13) | −0.0042 (13) | −0.0060 (11) |
C16 | 0.0469 (18) | 0.0400 (14) | 0.0323 (13) | 0.0025 (13) | −0.0034 (12) | 0.0033 (11) |
C17 | 0.0397 (16) | 0.0359 (13) | 0.0331 (13) | −0.0021 (12) | −0.0019 (11) | −0.0051 (10) |
C18 | 0.0298 (15) | 0.0357 (14) | 0.0315 (13) | 0.0000 (11) | −0.0016 (11) | −0.0033 (10) |
C19 | 0.0357 (16) | 0.0336 (13) | 0.0350 (14) | −0.0002 (11) | 0.0013 (12) | 0.0023 (10) |
C20 | 0.0318 (15) | 0.0475 (15) | 0.0341 (14) | 0.0018 (12) | 0.0004 (11) | 0.0041 (11) |
C21 | 0.0520 (19) | 0.0447 (16) | 0.0436 (15) | 0.0025 (14) | 0.0017 (13) | 0.0073 (12) |
C22 | 0.057 (2) | 0.063 (2) | 0.058 (2) | 0.0065 (17) | 0.0033 (16) | 0.0220 (16) |
C23 | 0.060 (2) | 0.093 (3) | 0.0373 (17) | 0.0018 (19) | −0.0141 (15) | 0.0005 (16) |
C24 | 0.054 (2) | 0.0558 (18) | 0.0427 (16) | 0.0007 (15) | −0.0102 (14) | −0.0016 (13) |
O6 | 0.129 (3) | 0.121 (3) | 0.0761 (19) | 0.025 (2) | −0.0020 (18) | −0.0038 (17) |
Ag1—N1 | 2.171 (2) | C5—H5 | 0.9300 |
Ag1—N5 | 2.173 (2) | C7—C8 | 1.461 (3) |
O1—C6 | 1.364 (3) | C8—C12 | 1.381 (4) |
O1—C7 | 1.367 (3) | C8—C9 | 1.384 (4) |
O2—C19 | 1.361 (3) | C9—C10 | 1.378 (4) |
O2—C18 | 1.361 (3) | C9—H9 | 0.9300 |
O3—N9 | 1.245 (4) | C10—H10 | 0.9300 |
O4—N9 | 1.250 (4) | C11—C12 | 1.381 (4) |
O5—N9 | 1.197 (3) | C11—H11 | 0.9300 |
N1—C4 | 1.339 (3) | C12—H12 | 0.9300 |
N1—C3 | 1.341 (3) | C13—C17 | 1.385 (3) |
N2—C6 | 1.289 (3) | C13—C14 | 1.390 (3) |
N2—N3 | 1.403 (3) | C13—C18 | 1.456 (3) |
N3—C7 | 1.285 (3) | C14—C15 | 1.374 (4) |
N4—C10 | 1.329 (4) | C14—H14 | 0.9300 |
N4—C11 | 1.331 (4) | C15—H15 | 0.9300 |
N5—C16 | 1.338 (3) | C16—C17 | 1.375 (3) |
N5—C15 | 1.341 (3) | C16—H16 | 0.9300 |
N6—C18 | 1.296 (3) | C17—H17 | 0.9300 |
N6—N7 | 1.404 (3) | C19—C20 | 1.462 (3) |
N7—C19 | 1.288 (3) | C20—C24 | 1.380 (4) |
N8—C23 | 1.327 (4) | C20—C21 | 1.386 (4) |
N8—C22 | 1.329 (4) | C21—C22 | 1.371 (4) |
C1—C2 | 1.389 (3) | C21—H21 | 0.9300 |
C1—C5 | 1.391 (3) | C22—H22 | 0.9300 |
C1—C6 | 1.458 (3) | C23—C24 | 1.383 (4) |
C2—C3 | 1.375 (3) | C23—H23 | 0.9300 |
C2—H2 | 0.9300 | C24—H24 | 0.9300 |
C3—H3 | 0.9300 | O6—H6A | 0.8505 |
C4—C5 | 1.372 (3) | O6—H6B | 0.8501 |
C4—H4 | 0.9300 | ||
N1—Ag1—N5 | 179.10 (8) | N4—C10—H10 | 117.8 |
C6—O1—C7 | 102.18 (18) | C9—C10—H10 | 117.8 |
C19—O2—C18 | 102.44 (18) | N4—C11—C12 | 124.9 (3) |
C4—N1—C3 | 117.5 (2) | N4—C11—H11 | 117.5 |
C4—N1—Ag1 | 122.40 (17) | C12—C11—H11 | 117.5 |
C3—N1—Ag1 | 120.05 (17) | C8—C12—C11 | 118.0 (3) |
C6—N2—N3 | 106.20 (19) | C8—C12—H12 | 121.0 |
C7—N3—N2 | 106.4 (2) | C11—C12—H12 | 121.0 |
C10—N4—C11 | 115.8 (2) | C17—C13—C14 | 118.9 (2) |
C16—N5—C15 | 117.8 (2) | C17—C13—C18 | 119.9 (2) |
C16—N5—Ag1 | 122.21 (17) | C14—C13—C18 | 121.2 (2) |
C15—N5—Ag1 | 119.95 (17) | C15—C14—C13 | 118.4 (2) |
C18—N6—N7 | 106.34 (19) | C15—C14—H14 | 120.8 |
C19—N7—N6 | 105.9 (2) | C13—C14—H14 | 120.8 |
C23—N8—C22 | 116.0 (3) | N5—C15—C14 | 123.2 (2) |
O5—N9—O3 | 121.6 (4) | N5—C15—H15 | 118.4 |
O5—N9—O4 | 121.0 (4) | C14—C15—H15 | 118.4 |
O3—N9—O4 | 117.3 (3) | N5—C16—C17 | 123.0 (2) |
C2—C1—C5 | 118.3 (2) | N5—C16—H16 | 118.5 |
C2—C1—C6 | 122.3 (2) | C17—C16—H16 | 118.5 |
C5—C1—C6 | 119.4 (2) | C16—C17—C13 | 118.7 (2) |
C3—C2—C1 | 118.8 (2) | C16—C17—H17 | 120.7 |
C3—C2—H2 | 120.6 | C13—C17—H17 | 120.7 |
C1—C2—H2 | 120.6 | N6—C18—O2 | 112.3 (2) |
N1—C3—C2 | 123.2 (2) | N6—C18—C13 | 128.7 (2) |
N1—C3—H3 | 118.4 | O2—C18—C13 | 119.0 (2) |
C2—C3—H3 | 118.4 | N7—C19—O2 | 113.0 (2) |
N1—C4—C5 | 123.3 (2) | N7—C19—C20 | 128.8 (2) |
N1—C4—H4 | 118.4 | O2—C19—C20 | 118.2 (2) |
C5—C4—H4 | 118.4 | C24—C20—C21 | 118.6 (3) |
C4—C5—C1 | 118.9 (2) | C24—C20—C19 | 121.1 (2) |
C4—C5—H5 | 120.6 | C21—C20—C19 | 120.3 (2) |
C1—C5—H5 | 120.6 | C22—C21—C20 | 118.4 (3) |
N2—C6—O1 | 112.6 (2) | C22—C21—H21 | 120.8 |
N2—C6—C1 | 127.2 (2) | C20—C21—H21 | 120.8 |
O1—C6—C1 | 120.1 (2) | N8—C22—C21 | 124.4 (3) |
N3—C7—O1 | 112.6 (2) | N8—C22—H22 | 117.8 |
N3—C7—C8 | 127.7 (2) | C21—C22—H22 | 117.8 |
O1—C7—C8 | 119.7 (2) | N8—C23—C24 | 124.8 (3) |
C12—C8—C9 | 118.3 (2) | N8—C23—H23 | 117.6 |
C12—C8—C7 | 123.1 (2) | C24—C23—H23 | 117.6 |
C9—C8—C7 | 118.6 (2) | C20—C24—C23 | 117.7 (3) |
C10—C9—C8 | 118.7 (3) | C20—C24—H24 | 121.1 |
C10—C9—H9 | 120.7 | C23—C24—H24 | 121.1 |
C8—C9—H9 | 120.7 | H6A—O6—H6B | 117.1 |
N4—C10—C9 | 124.4 (3) | ||
C6—N2—N3—C7 | −0.1 (3) | N4—C11—C12—C8 | 0.3 (5) |
C18—N6—N7—C19 | 0.1 (3) | C17—C13—C14—C15 | −0.5 (4) |
C5—C1—C2—C3 | −0.6 (4) | C18—C13—C14—C15 | 179.2 (2) |
C6—C1—C2—C3 | 179.6 (2) | C16—N5—C15—C14 | −0.2 (4) |
C4—N1—C3—C2 | 0.0 (4) | Ag1—N5—C15—C14 | 177.4 (2) |
Ag1—N1—C3—C2 | −178.8 (2) | C13—C14—C15—N5 | 0.8 (4) |
C1—C2—C3—N1 | 0.0 (4) | C15—N5—C16—C17 | −0.7 (4) |
C3—N1—C4—C5 | 0.6 (4) | Ag1—N5—C16—C17 | −178.3 (2) |
Ag1—N1—C4—C5 | 179.4 (2) | N5—C16—C17—C13 | 1.0 (4) |
N1—C4—C5—C1 | −1.2 (4) | C14—C13—C17—C16 | −0.4 (4) |
C2—C1—C5—C4 | 1.2 (4) | C18—C13—C17—C16 | 179.9 (2) |
C6—C1—C5—C4 | −179.0 (2) | N7—N6—C18—O2 | 0.4 (3) |
N3—N2—C6—O1 | −0.3 (3) | N7—N6—C18—C13 | −178.9 (2) |
N3—N2—C6—C1 | 178.2 (2) | C19—O2—C18—N6 | −0.7 (3) |
C7—O1—C6—N2 | 0.6 (3) | C19—O2—C18—C13 | 178.7 (2) |
C7—O1—C6—C1 | −178.1 (2) | C17—C13—C18—N6 | 5.0 (4) |
C2—C1—C6—N2 | 173.4 (3) | C14—C13—C18—N6 | −174.7 (3) |
C5—C1—C6—N2 | −6.4 (4) | C17—C13—C18—O2 | −174.3 (2) |
C2—C1—C6—O1 | −8.2 (4) | C14—C13—C18—O2 | 6.1 (4) |
C5—C1—C6—O1 | 172.0 (2) | N6—N7—C19—O2 | −0.5 (3) |
N2—N3—C7—O1 | 0.5 (3) | N6—N7—C19—C20 | 179.2 (3) |
N2—N3—C7—C8 | −179.2 (2) | C18—O2—C19—N7 | 0.7 (3) |
C6—O1—C7—N3 | −0.6 (3) | C18—O2—C19—C20 | −179.0 (2) |
C6—O1—C7—C8 | 179.1 (2) | N7—C19—C20—C24 | 166.7 (3) |
N3—C7—C8—C12 | −167.0 (3) | O2—C19—C20—C24 | −13.6 (4) |
O1—C7—C8—C12 | 13.3 (4) | N7—C19—C20—C21 | −12.8 (4) |
N3—C7—C8—C9 | 12.0 (4) | O2—C19—C20—C21 | 166.9 (2) |
O1—C7—C8—C9 | −167.7 (2) | C24—C20—C21—C22 | −0.4 (4) |
C12—C8—C9—C10 | −0.2 (4) | C19—C20—C21—C22 | 179.2 (3) |
C7—C8—C9—C10 | −179.2 (3) | C23—N8—C22—C21 | −0.3 (5) |
C11—N4—C10—C9 | 0.7 (5) | C20—C21—C22—N8 | 0.3 (5) |
C8—C9—C10—N4 | −0.3 (5) | C22—N8—C23—C24 | 0.3 (5) |
C10—N4—C11—C12 | −0.7 (5) | C21—C20—C24—C23 | 0.4 (4) |
C9—C8—C12—C11 | 0.2 (4) | C19—C20—C24—C23 | −179.2 (3) |
C7—C8—C12—C11 | 179.2 (3) | N8—C23—C24—C20 | −0.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O4i | 0.85 | 2.22 | 2.949 (5) | 144 |
O6—H6B···O3 | 0.85 | 2.29 | 3.014 (5) | 144 |
C4—H4···O5ii | 0.93 | 2.49 | 3.228 (4) | 137 |
C5—H5···N2iii | 0.93 | 2.55 | 3.443 (3) | 161 |
C9—H9···O4iv | 0.93 | 2.58 | 3.197 (4) | 125 |
C15—H15···O3ii | 0.93 | 2.56 | 3.481 (4) | 169 |
C17—H17···N6v | 0.93 | 2.57 | 3.467 (3) | 163 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z; (iv) x, y−1, z; (v) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C12H8N4O)2]NO3·H2O |
Mr | 636.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 7.3200 (19), 13.281 (3), 25.002 (6) |
β (°) | 92.664 (3) |
V (Å3) | 2428.0 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.89 |
Crystal size (mm) | 0.14 × 0.13 × 0.09 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.781, 0.849 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13051, 4287, 3232 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.02 |
No. of reflections | 4287 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.39 |
Computer programs: , APEX2 (Bruker, 2003) and SAINT (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg, 2005), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O4i | 0.85 | 2.22 | 2.949 (5) | 144 |
O6—H6B···O3 | 0.85 | 2.29 | 3.014 (5) | 144 |
C4—H4···O5ii | 0.93 | 2.49 | 3.228 (4) | 137 |
C5—H5···N2iii | 0.93 | 2.55 | 3.443 (3) | 161 |
C9—H9···O4iv | 0.93 | 2.58 | 3.197 (4) | 125 |
C15—H15···O3ii | 0.93 | 2.56 | 3.481 (4) | 169 |
C17—H17···N6v | 0.93 | 2.57 | 3.467 (3) | 163 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z; (iv) x, y−1, z; (v) −x+2, −y+2, −z. |
The angular dipyridyl ligand, 2,5-di-4-pyridyl-1,3,4-oxadiazole (4-bpo), has been demonstrated to be an excellent building block to assemble with familiar transition metal ions, which produces a variety of coordination complexes from 0-D to 3-D (Du et al., 2005, 2006, 2007). With respect to AgI complexes, these are usually coordination polymers with infinite coordination arrays, in which the 4-bpo ligands display either µ-Npy, Npy or µ3-Npy, Npy, Noxadiazole bridging coordination modes (Dong et al., 2003; Du & Zhao, 2004). For instance, self-assembly of AgNO3 with 4-bpo through slow diffusion in CH3CN/CHCl3 yields a chain complex [Ag(4-bpo)(NO3)], in which the trigonal AgI centers are bridged by 4-bpo in µ-Npy, Npy fashion (Guo et al., 2003). Herein, we describe a related complex [Ag(4-bpo)2](NO3)(H2O) (I) prepared under hydrothermal condition, which has an unexpected mononuclear structure.
The molecular structure of the title compound (I) is shown in Fig. 1. The AgI ion is coordinated by two N atoms of the pyridyl rings from two separate monodentate 4-bpo ligands in trans-arrangement [Ag1—N1 = 2.171 (2) Å and Ag1—N5 = 2.173 (2) Å], displaying a linear geometry [N1—Ag1—N5 = 179.10 (8)°]. There is also a weak Ag1—O5 (2.836 (3) Å) contact between each AgI center and the adjacent nitrate anion. The two pyridyl rings in one 4-bpo ligand are inclined by 7.9 (4) and 12.7 (4)° with respect to the central oxadiazole plane, and by 10.6 (1)° with respect to each other. Corresponding values for the other 4-bpo molecule are 5.9 (2), 13.3 (1), and 10.7 (2)°. Interestingly, each nitrate acts as the acceptor of a pair of O—H···O bonds with the neighboring two water molecules, and thus, a supramolecular chain along the [100] direction is afforded. Two adjacent such 1-D chains are interdigitated and further combined to give a double-strand supramolecular array (see Fig. 2), via interchain parallel π–π stacking forces (center-to-center distances between the corresponding aromatic rings in 4-bpo are in the range of 3.61–3.72 Å). In addition, multiple C—H···O and C—H···N interactions (see Table) are observed to consolidate this crystalline lattice.