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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103007613/ob1118sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007613/ob1118Isup2.hkl |
CCDC reference: 200614
The synthesis of the title compound, (I), was performed in the dark. A solution of AgNO3 (170 mg, 1 mmol) in 10 ml CH3OH was added to a stired solution of 4-[N,N-bis(2-cyanoethyl)amino]pyridine (400 mg, 2 mmol) in CH3OH (20 ml) at room temperature, the reaction mixture was stired for 1 h and filtered. A solution of NaClO4 (122.5 mg, 1 mmol) in CH3OH (5 ml) was added to the clear filtrate and stired for 15 min. The reaction mixture was filtered again, and colorless single crystals of (I) suitable for X-ray analysis were obtained after several days by slow evaporation of the filtrate.
Analysis calculated for AgC22H24N8O4Cl: C 43.47, H 3.98, N 18.44; found: C 43.35, H 4.01, N 18.40.
The positions of all H atoms were fixed geometrically, and distances to H atoms were set by the program SHELXTL (Bruker, 2000)?.
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Ag(C11H12N4)2](ClO4) | Z = 4 |
Mr = 607.81 | F(000) = 1232 |
Triclinic, P1 | Dx = 1.574 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.221 (2) Å | Cell parameters from 2238 reflections |
b = 14.457 (2) Å | θ = 2.7–22.3° |
c = 19.897 (2) Å | µ = 0.94 mm−1 |
α = 76.39 (1)° | T = 293 K |
β = 84.20 (1)° | Block, colorless |
γ = 88.06 (1)° | 0.3 × 0.3 × 0.2 mm |
V = 2564.6 (7) Å3 |
Bruker Smart Apex CCD area detector diffractometer | 8825 independent reflections |
Radiation source: sealed tube | 6422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: empirical (using intensity measurements) SADABS; Bruker, 2000 | h = −11→11 |
Tmin = 0.762, Tmax = 0.827 | k = −17→11 |
13111 measured reflections | l = −24→23 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0418P)2 + 1.1404P] where P = (Fo2 + 2Fc2)/3 |
8825 reflections | (Δ/σ)max < 0.001 |
601 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.98 e Å−3 |
[Ag(C11H12N4)2](ClO4) | γ = 88.06 (1)° |
Mr = 607.81 | V = 2564.6 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.221 (2) Å | Mo Kα radiation |
b = 14.457 (2) Å | µ = 0.94 mm−1 |
c = 19.897 (2) Å | T = 293 K |
α = 76.39 (1)° | 0.3 × 0.3 × 0.2 mm |
β = 84.20 (1)° |
Bruker Smart Apex CCD area detector diffractometer | 8825 independent reflections |
Absorption correction: empirical (using intensity measurements) SADABS; Bruker, 2000 | 6422 reflections with I > 2σ(I) |
Tmin = 0.762, Tmax = 0.827 | Rint = 0.018 |
13111 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.83 e Å−3 |
8825 reflections | Δρmin = −0.98 e Å−3 |
601 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 8.5985 (0.0057) x − 4.7604 (0.0222) y + 0.0151 (0.0294) z = 0.4068 (0.0268) * 0.0077 (0.0026) N1 * −0.0066 (0.0029) C1 * 0.0000 (0.0029) C2 * 0.0053 (0.0028) C3 * −0.0042 (0.0028) C4 * −0.0022 (0.0027) C5 Rms deviation of fitted atoms = 0.0051 − 3.6847 (0.0133) x + 12.8624 (0.0107) y + 0.4139 (0.0281) z = 9.2453 (0.0179) Angle to previous plane (with approximate e.s.d.) = 45.78 (0.15) * −0.0122 (0.0025) N5 * −0.0014 (0.0026) C12 * 0.0137 (0.0026) C13 * −0.0128 (0.0025) C14 * 0.0000 (0.0026) C15 * 0.0128 (0.0027) C16 Rms deviation of fitted atoms = 0.0105 Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.8487 (0.0079) x − 6.1431 (0.0213) y + 4.6860 (0.0290) z = 7.7192 (0.0368) * −0.0085 (0.0027) N9 * 0.0104 (0.0029) C23 * 0.0021 (0.0028) C24 * −0.0157 (0.0027) C25 * 0.0179 (0.0027) C26 * −0.0062 (0.0027) C27 Rms deviation of fitted atoms = 0.0115 8.5003 (0.0066) x − 5.1466 (0.0239) y − 0.1481 (0.0314) z = 4.9497 (0.0338) Angle to previous plane (with approximate e.s.d.) = 16.74 (0.17) * −0.0201 (0.0028) N13 * 0.0189 (0.0030) C34 * −0.0056 (0.0030) C35 * −0.0057 (0.0029) C36 * 0.0042 (0.0030) C37 * 0.0081 (0.0031) C38 Rms deviation of fitted atoms = 0.0123 |
Refinement. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. 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 | 0.53776 (4) | 0.84897 (3) | 0.247521 (16) | 0.05426 (12) | |
Ag2 | 0.97604 (4) | 0.65100 (3) | 0.774192 (16) | 0.05707 (13) | |
C1 | 0.5323 (4) | 0.8787 (3) | 0.3968 (2) | 0.0434 (10) | |
H1 | 0.5641 | 0.9392 | 0.3733 | 0.052* | |
C2 | 0.5211 (4) | 0.8573 (3) | 0.4688 (2) | 0.0434 (10) | |
H2 | 0.5461 | 0.9023 | 0.4922 | 0.052* | |
C3 | 0.4709 (4) | 0.7656 (3) | 0.5069 (2) | 0.0394 (10) | |
C4 | 0.4347 (4) | 0.7021 (3) | 0.4671 (2) | 0.0395 (9) | |
H4 | 0.4003 | 0.6417 | 0.4891 | 0.047* | |
C5 | 0.4507 (4) | 0.7303 (3) | 0.3947 (2) | 0.0407 (10) | |
H5 | 0.4262 | 0.6872 | 0.3697 | 0.049* | |
C12 | 0.4846 (4) | 0.8544 (3) | 0.09566 (19) | 0.0364 (9) | |
H12 | 0.3959 | 0.8281 | 0.1167 | 0.044* | |
C13 | 0.5121 (4) | 0.8657 (3) | 0.02576 (19) | 0.0372 (9) | |
H13 | 0.4413 | 0.8484 | 0.0010 | 0.045* | |
C14 | 0.6454 (4) | 0.9030 (3) | −0.01036 (19) | 0.0337 (9) | |
C15 | 0.7442 (4) | 0.9309 (3) | 0.03290 (19) | 0.0388 (9) | |
H15 | 0.8340 | 0.9572 | 0.0137 | 0.047* | |
C16 | 0.7037 (4) | 0.9181 (3) | 0.1031 (2) | 0.0411 (10) | |
H16 | 0.7688 | 0.9381 | 0.1295 | 0.049* | |
C6 | 0.4963 (5) | 0.8115 (3) | 0.6195 (2) | 0.0479 (11) | |
H6A | 0.4459 | 0.7937 | 0.6658 | 0.057* | |
H6B | 0.4617 | 0.8741 | 0.5970 | 0.057* | |
C7 | 0.6614 (5) | 0.8144 (3) | 0.6246 (2) | 0.0573 (12) | |
H7A | 0.6961 | 0.7519 | 0.6473 | 0.069* | |
H7B | 0.7121 | 0.8319 | 0.5783 | 0.069* | |
C8 | 0.6925 (5) | 0.8844 (4) | 0.6644 (3) | 0.0612 (13) | |
C9 | 0.4085 (5) | 0.6463 (3) | 0.6176 (2) | 0.0460 (11) | |
H9A | 0.3163 | 0.6322 | 0.6041 | 0.055* | |
H9B | 0.4004 | 0.6413 | 0.6668 | 0.055* | |
C10 | 0.5249 (5) | 0.5706 (3) | 0.6391 (2) | 0.0479 (11) | |
H10A | 0.5910 | 0.5950 | 0.6657 | 0.058* | |
H10B | 0.4779 | 0.5152 | 0.6696 | 0.058* | |
C11 | 0.6119 (5) | 0.5400 (3) | 0.5813 (2) | 0.0486 (11) | |
C17 | 0.8345 (4) | 0.9317 (3) | −0.1133 (2) | 0.0428 (10) | |
H17A | 0.8550 | 0.8924 | −0.1466 | 0.051* | |
H17B | 0.9014 | 0.9125 | −0.0778 | 0.051* | |
C18 | 0.8635 (5) | 1.0385 (3) | −0.1513 (2) | 0.0515 (11) | |
H18A | 0.9492 | 1.0417 | −0.1843 | 0.062* | |
H18B | 0.7814 | 1.0633 | −0.1772 | 0.062* | |
C19 | 0.8861 (5) | 1.0996 (3) | −0.1025 (2) | 0.0492 (11) | |
C20 | 0.5745 (4) | 0.8995 (3) | −0.1267 (2) | 0.0420 (10) | |
H20A | 0.5912 | 0.9461 | −0.1705 | 0.050* | |
H20B | 0.4778 | 0.9114 | −0.1061 | 0.050* | |
C21 | 0.5787 (5) | 0.7987 (3) | −0.1413 (2) | 0.0496 (11) | |
H21A | 0.5256 | 0.8005 | −0.1812 | 0.059* | |
H21B | 0.6792 | 0.7821 | −0.1533 | 0.059* | |
C22 | 0.5168 (6) | 0.7235 (3) | −0.0828 (2) | 0.0560 (12) | |
C23 | 0.9650 (5) | 0.6777 (3) | 0.9217 (2) | 0.0461 (11) | |
H23 | 1.0219 | 0.7297 | 0.8988 | 0.055* | |
C24 | 0.9167 (4) | 0.6712 (3) | 0.99213 (19) | 0.0391 (9) | |
H24 | 0.9403 | 0.7174 | 1.0146 | 0.047* | |
C25 | 0.8291 (4) | 0.5898 (3) | 1.02835 (19) | 0.0375 (9) | |
C26 | 0.8037 (4) | 0.5221 (3) | 0.9895 (2) | 0.0382 (9) | |
H26 | 0.7526 | 0.4669 | 1.0107 | 0.046* | |
C27 | 0.8551 (4) | 0.5389 (3) | 0.9203 (2) | 0.0421 (10) | |
H27 | 0.8328 | 0.4945 | 0.8959 | 0.051* | |
C34 | 1.0597 (5) | 0.7668 (3) | 0.6260 (2) | 0.0459 (11) | |
H34 | 1.0911 | 0.8087 | 0.6503 | 0.055* | |
C35 | 1.0734 (4) | 0.7962 (3) | 0.5533 (2) | 0.0427 (10) | |
H35 | 1.1077 | 0.8566 | 0.5313 | 0.051* | |
C36 | 1.0339 (4) | 0.7321 (3) | 0.51331 (19) | 0.0403 (10) | |
C37 | 0.9803 (5) | 0.6406 (3) | 0.5548 (2) | 0.0455 (10) | |
H37 | 0.9524 | 0.5944 | 0.5332 | 0.055* | |
C38 | 0.9713 (5) | 0.6228 (3) | 0.6263 (2) | 0.0498 (11) | |
H38 | 0.9385 | 0.5633 | 0.6512 | 0.060* | |
C28 | 0.6938 (5) | 0.4972 (3) | 1.1372 (2) | 0.0460 (11) | |
H28A | 0.7035 | 0.4905 | 1.1862 | 0.055* | |
H28B | 0.7347 | 0.4405 | 1.1241 | 0.055* | |
C29 | 0.5302 (5) | 0.5065 (3) | 1.1247 (2) | 0.0471 (11) | |
H29A | 0.4942 | 0.5690 | 1.1286 | 0.056* | |
H29B | 0.5189 | 0.5003 | 1.0780 | 0.056* | |
C30 | 0.4438 (5) | 0.4327 (3) | 1.1755 (2) | 0.0505 (12) | |
C31 | 0.7726 (4) | 0.6607 (3) | 1.1305 (2) | 0.0428 (10) | |
H31A | 0.6855 | 0.6563 | 1.1628 | 0.051* | |
H31B | 0.7672 | 0.7201 | 1.0959 | 0.051* | |
C32 | 0.9082 (5) | 0.6623 (3) | 1.1706 (2) | 0.0504 (11) | |
H32A | 0.9199 | 0.6007 | 1.2021 | 0.060* | |
H32B | 0.9948 | 0.6740 | 1.1379 | 0.060* | |
C33 | 0.8936 (5) | 0.7356 (3) | 1.2098 (2) | 0.0496 (11) | |
C39 | 1.0031 (5) | 0.6828 (3) | 0.4051 (2) | 0.0499 (11) | |
H39A | 1.0382 | 0.6203 | 0.4274 | 0.060* | |
H39B | 1.0494 | 0.6992 | 0.3579 | 0.060* | |
C40 | 0.8382 (5) | 0.6796 (3) | 0.4032 (2) | 0.0544 (12) | |
H40A | 0.7916 | 0.6634 | 0.4503 | 0.065* | |
H40B | 0.8029 | 0.7420 | 0.3806 | 0.065* | |
C41 | 0.7976 (6) | 0.6071 (4) | 0.3645 (3) | 0.0628 (13) | |
C42 | 1.1048 (5) | 0.8455 (3) | 0.4003 (2) | 0.0470 (11) | |
H42A | 1.1700 | 0.8330 | 0.3620 | 0.056* | |
H42B | 1.1622 | 0.8728 | 0.4289 | 0.056* | |
C43 | 0.9903 (5) | 0.9193 (3) | 0.3707 (2) | 0.0538 (12) | |
H43A | 1.0396 | 0.9741 | 0.3404 | 0.065* | |
H43B | 0.9309 | 0.8920 | 0.3429 | 0.065* | |
C44 | 0.8975 (5) | 0.9502 (3) | 0.4238 (3) | 0.0543 (12) | |
N1 | 0.5002 (4) | 0.8175 (2) | 0.35835 (16) | 0.0399 (8) | |
N2 | 0.4633 (4) | 0.7409 (2) | 0.57875 (16) | 0.0446 (8) | |
N3 | 0.7106 (6) | 0.9386 (4) | 0.6962 (2) | 0.0874 (15) | |
N4 | 0.6766 (5) | 0.5155 (3) | 0.5373 (2) | 0.0657 (11) | |
N5 | 0.5785 (4) | 0.8792 (2) | 0.13680 (16) | 0.0412 (8) | |
N6 | 0.6825 (3) | 0.9137 (2) | −0.08030 (16) | 0.0369 (8) | |
N7 | 0.9059 (4) | 1.1438 (3) | −0.0644 (2) | 0.0590 (10) | |
N8 | 0.4748 (6) | 0.6645 (3) | −0.0383 (2) | 0.0814 (14) | |
N9 | 0.9354 (4) | 0.6149 (2) | 0.88488 (17) | 0.0468 (9) | |
N10 | 0.7759 (4) | 0.5817 (2) | 1.09634 (16) | 0.0421 (8) | |
N11 | 0.3764 (5) | 0.3743 (3) | 1.21703 (19) | 0.0634 (11) | |
N12 | 0.8767 (4) | 0.7938 (3) | 1.2410 (2) | 0.0597 (11) | |
N13 | 1.0061 (4) | 0.6847 (2) | 0.66301 (16) | 0.0452 (9) | |
N14 | 1.0443 (4) | 0.7527 (2) | 0.44280 (16) | 0.0425 (8) | |
N15 | 0.7727 (5) | 0.5546 (3) | 0.3337 (2) | 0.0711 (13) | |
N16 | 0.8238 (5) | 0.9759 (3) | 0.4662 (3) | 0.0760 (13) | |
Cl2 | 0.20629 (14) | 0.86994 (10) | 0.77829 (7) | 0.0678 (3) | |
O5 | 0.2578 (3) | 0.7736 (2) | 0.77718 (16) | 0.0678 (3) | |
O6 | 0.2955 (4) | 0.9367 (2) | 0.73160 (17) | 0.0678 (3) | |
O7 | 0.0561 (4) | 0.8739 (2) | 0.76139 (17) | 0.0678 (3) | |
O8 | 0.2031 (3) | 0.8823 (2) | 0.84745 (17) | 0.0678 (3) | |
Cl1 | 0.71035 (12) | 0.34676 (8) | 0.76277 (6) | 0.0525 (2) | |
O1 | 0.7497 (3) | 0.2514 (2) | 0.75398 (15) | 0.0525 (2) | |
O2 | 0.7961 (3) | 0.4156 (2) | 0.71250 (15) | 0.0525 (2) | |
O3 | 0.5571 (3) | 0.3632 (2) | 0.75459 (15) | 0.0525 (2) | |
O4 | 0.7356 (3) | 0.3526 (2) | 0.83252 (15) | 0.0525 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0691 (3) | 0.0643 (2) | 0.02670 (18) | 0.00383 (18) | −0.00010 (16) | −0.00761 (15) |
Ag2 | 0.0653 (3) | 0.0747 (3) | 0.02777 (19) | 0.00534 (19) | 0.00058 (16) | −0.00810 (16) |
C1 | 0.055 (3) | 0.037 (2) | 0.034 (2) | −0.004 (2) | 0.003 (2) | −0.0028 (19) |
C2 | 0.056 (3) | 0.041 (2) | 0.035 (2) | −0.008 (2) | −0.005 (2) | −0.0090 (18) |
C3 | 0.045 (2) | 0.040 (2) | 0.035 (2) | −0.0058 (19) | −0.0027 (19) | −0.0123 (18) |
C4 | 0.043 (2) | 0.036 (2) | 0.042 (2) | −0.0013 (18) | −0.0033 (19) | −0.0132 (18) |
C5 | 0.047 (3) | 0.040 (2) | 0.040 (2) | 0.0013 (19) | −0.0037 (19) | −0.0184 (19) |
C12 | 0.036 (2) | 0.038 (2) | 0.035 (2) | −0.0001 (17) | −0.0004 (18) | −0.0074 (18) |
C13 | 0.042 (2) | 0.036 (2) | 0.035 (2) | 0.0013 (18) | −0.0041 (18) | −0.0098 (17) |
C14 | 0.039 (2) | 0.033 (2) | 0.031 (2) | −0.0012 (17) | −0.0029 (18) | −0.0109 (17) |
C15 | 0.043 (2) | 0.039 (2) | 0.035 (2) | −0.0095 (18) | −0.0067 (18) | −0.0053 (18) |
C16 | 0.048 (3) | 0.039 (2) | 0.036 (2) | −0.0060 (19) | −0.0075 (19) | −0.0047 (18) |
C6 | 0.054 (3) | 0.053 (3) | 0.037 (2) | −0.009 (2) | −0.001 (2) | −0.011 (2) |
C7 | 0.057 (3) | 0.065 (3) | 0.047 (3) | −0.011 (2) | −0.001 (2) | −0.007 (2) |
C8 | 0.065 (3) | 0.066 (3) | 0.053 (3) | −0.017 (3) | −0.007 (3) | −0.011 (3) |
C9 | 0.055 (3) | 0.047 (3) | 0.034 (2) | −0.008 (2) | −0.005 (2) | −0.0024 (19) |
C10 | 0.060 (3) | 0.045 (3) | 0.039 (2) | −0.012 (2) | −0.004 (2) | −0.008 (2) |
C11 | 0.059 (3) | 0.039 (3) | 0.047 (3) | −0.014 (2) | −0.004 (2) | −0.006 (2) |
C17 | 0.040 (2) | 0.044 (3) | 0.042 (2) | −0.0062 (19) | 0.0083 (19) | −0.0073 (19) |
C18 | 0.047 (3) | 0.053 (3) | 0.046 (3) | −0.008 (2) | 0.010 (2) | 0.000 (2) |
C19 | 0.041 (3) | 0.046 (3) | 0.052 (3) | −0.004 (2) | 0.006 (2) | 0.002 (2) |
C20 | 0.047 (3) | 0.042 (2) | 0.038 (2) | 0.0036 (19) | −0.0032 (19) | −0.0125 (19) |
C21 | 0.066 (3) | 0.041 (3) | 0.042 (2) | −0.002 (2) | −0.008 (2) | −0.011 (2) |
C22 | 0.081 (4) | 0.038 (3) | 0.050 (3) | −0.005 (2) | −0.005 (3) | −0.014 (2) |
C23 | 0.052 (3) | 0.048 (3) | 0.035 (2) | −0.010 (2) | −0.001 (2) | −0.003 (2) |
C24 | 0.043 (2) | 0.040 (2) | 0.034 (2) | −0.0046 (19) | −0.0011 (18) | −0.0088 (18) |
C25 | 0.040 (2) | 0.042 (2) | 0.032 (2) | −0.0042 (18) | −0.0008 (18) | −0.0124 (18) |
C26 | 0.038 (2) | 0.038 (2) | 0.040 (2) | −0.0015 (18) | −0.0015 (18) | −0.0113 (18) |
C27 | 0.043 (2) | 0.046 (3) | 0.037 (2) | 0.000 (2) | −0.0040 (19) | −0.0093 (19) |
C34 | 0.058 (3) | 0.049 (3) | 0.037 (2) | −0.010 (2) | −0.008 (2) | −0.019 (2) |
C35 | 0.055 (3) | 0.041 (2) | 0.033 (2) | −0.010 (2) | −0.0046 (19) | −0.0090 (18) |
C36 | 0.051 (3) | 0.042 (2) | 0.029 (2) | −0.0074 (19) | −0.0050 (19) | −0.0094 (18) |
C37 | 0.059 (3) | 0.042 (3) | 0.034 (2) | −0.008 (2) | −0.004 (2) | −0.0063 (19) |
C38 | 0.063 (3) | 0.047 (3) | 0.036 (2) | −0.006 (2) | −0.009 (2) | 0.000 (2) |
C28 | 0.055 (3) | 0.044 (3) | 0.039 (2) | −0.013 (2) | 0.007 (2) | −0.0134 (19) |
C29 | 0.056 (3) | 0.045 (3) | 0.044 (3) | −0.016 (2) | 0.011 (2) | −0.022 (2) |
C30 | 0.064 (3) | 0.058 (3) | 0.037 (2) | −0.019 (2) | 0.009 (2) | −0.029 (2) |
C31 | 0.046 (3) | 0.044 (2) | 0.039 (2) | −0.0022 (19) | 0.002 (2) | −0.0154 (19) |
C32 | 0.053 (3) | 0.051 (3) | 0.047 (3) | −0.002 (2) | −0.001 (2) | −0.012 (2) |
C33 | 0.054 (3) | 0.052 (3) | 0.044 (3) | −0.011 (2) | −0.010 (2) | −0.011 (2) |
C39 | 0.061 (3) | 0.054 (3) | 0.036 (2) | −0.007 (2) | −0.003 (2) | −0.013 (2) |
C40 | 0.057 (3) | 0.062 (3) | 0.043 (3) | −0.004 (2) | 0.000 (2) | −0.013 (2) |
C41 | 0.065 (3) | 0.065 (4) | 0.055 (3) | −0.015 (3) | −0.009 (3) | −0.004 (3) |
C42 | 0.054 (3) | 0.046 (3) | 0.037 (2) | −0.012 (2) | 0.005 (2) | −0.0058 (19) |
C43 | 0.057 (3) | 0.050 (3) | 0.050 (3) | −0.019 (2) | −0.004 (2) | −0.001 (2) |
C44 | 0.050 (3) | 0.051 (3) | 0.058 (3) | −0.017 (2) | −0.002 (3) | −0.003 (2) |
N1 | 0.047 (2) | 0.046 (2) | 0.0271 (17) | −0.0007 (16) | 0.0005 (15) | −0.0118 (15) |
N2 | 0.052 (2) | 0.048 (2) | 0.0338 (19) | −0.0103 (17) | −0.0022 (16) | −0.0103 (16) |
N3 | 0.105 (4) | 0.093 (4) | 0.078 (3) | −0.027 (3) | −0.011 (3) | −0.041 (3) |
N4 | 0.075 (3) | 0.051 (3) | 0.068 (3) | −0.007 (2) | 0.003 (2) | −0.011 (2) |
N5 | 0.048 (2) | 0.042 (2) | 0.0318 (18) | −0.0006 (16) | −0.0010 (16) | −0.0070 (15) |
N6 | 0.0386 (19) | 0.0396 (19) | 0.0330 (18) | −0.0042 (15) | −0.0003 (15) | −0.0103 (14) |
N7 | 0.055 (3) | 0.052 (3) | 0.068 (3) | −0.0058 (19) | −0.003 (2) | −0.013 (2) |
N8 | 0.126 (4) | 0.053 (3) | 0.068 (3) | −0.012 (3) | 0.006 (3) | −0.024 (2) |
N9 | 0.055 (2) | 0.052 (2) | 0.0335 (19) | −0.0009 (18) | −0.0027 (17) | −0.0099 (17) |
N10 | 0.050 (2) | 0.043 (2) | 0.0343 (19) | −0.0096 (16) | 0.0042 (16) | −0.0137 (15) |
N11 | 0.079 (3) | 0.070 (3) | 0.042 (2) | −0.027 (2) | 0.015 (2) | −0.020 (2) |
N12 | 0.073 (3) | 0.061 (3) | 0.046 (2) | −0.022 (2) | −0.009 (2) | −0.011 (2) |
N13 | 0.057 (2) | 0.049 (2) | 0.0305 (19) | −0.0063 (18) | −0.0016 (17) | −0.0100 (17) |
N14 | 0.056 (2) | 0.044 (2) | 0.0281 (18) | −0.0104 (16) | −0.0011 (16) | −0.0094 (15) |
N15 | 0.092 (3) | 0.059 (3) | 0.066 (3) | −0.030 (2) | −0.020 (2) | −0.012 (2) |
N16 | 0.071 (3) | 0.069 (3) | 0.087 (4) | −0.031 (2) | 0.009 (3) | −0.018 (3) |
Cl2 | 0.0657 (7) | 0.0775 (7) | 0.0603 (6) | −0.0101 (5) | 0.0057 (5) | −0.0196 (5) |
O5 | 0.0657 (7) | 0.0775 (7) | 0.0603 (6) | −0.0101 (5) | 0.0057 (5) | −0.0196 (5) |
O6 | 0.0657 (7) | 0.0775 (7) | 0.0603 (6) | −0.0101 (5) | 0.0057 (5) | −0.0196 (5) |
O7 | 0.0657 (7) | 0.0775 (7) | 0.0603 (6) | −0.0101 (5) | 0.0057 (5) | −0.0196 (5) |
O8 | 0.0657 (7) | 0.0775 (7) | 0.0603 (6) | −0.0101 (5) | 0.0057 (5) | −0.0196 (5) |
Cl1 | 0.0508 (5) | 0.0519 (5) | 0.0518 (5) | 0.0007 (4) | 0.0035 (4) | −0.0094 (4) |
O1 | 0.0508 (5) | 0.0519 (5) | 0.0518 (5) | 0.0007 (4) | 0.0035 (4) | −0.0094 (4) |
O2 | 0.0508 (5) | 0.0519 (5) | 0.0518 (5) | 0.0007 (4) | 0.0035 (4) | −0.0094 (4) |
O3 | 0.0508 (5) | 0.0519 (5) | 0.0518 (5) | 0.0007 (4) | 0.0035 (4) | −0.0094 (4) |
O4 | 0.0508 (5) | 0.0519 (5) | 0.0518 (5) | 0.0007 (4) | 0.0035 (4) | −0.0094 (4) |
Ag1—N1 | 2.139 (3) | C23—H23 | 0.9300 |
Ag1—N5 | 2.139 (3) | C24—C25 | 1.451 (5) |
Ag2—N9 | 2.138 (3) | C24—H24 | 0.9300 |
Ag2—N13 | 2.142 (3) | C25—N10 | 1.371 (5) |
C1—N1 | 1.356 (5) | C25—C26 | 1.420 (5) |
C1—C2 | 1.387 (5) | C26—C27 | 1.379 (5) |
C1—H1 | 0.9300 | C26—H26 | 0.9300 |
C2—C3 | 1.430 (5) | C27—N9 | 1.356 (5) |
C2—H2 | 0.9300 | C27—H27 | 0.9300 |
C3—N2 | 1.384 (5) | C34—N13 | 1.323 (5) |
C3—C4 | 1.415 (5) | C34—C35 | 1.402 (5) |
C4—C5 | 1.396 (5) | C34—H34 | 0.9300 |
C4—H4 | 0.9300 | C35—C36 | 1.433 (5) |
C5—N1 | 1.365 (5) | C35—H35 | 0.9300 |
C5—H5 | 0.9300 | C36—N14 | 1.358 (5) |
C12—N5 | 1.360 (5) | C36—C37 | 1.458 (5) |
C12—C13 | 1.360 (5) | C37—C38 | 1.380 (5) |
C12—H12 | 0.9300 | C37—H37 | 0.9300 |
C13—C14 | 1.416 (5) | C38—N13 | 1.345 (5) |
C13—H13 | 0.9300 | C38—H38 | 0.9300 |
C14—N6 | 1.372 (5) | C28—N10 | 1.482 (5) |
C14—C15 | 1.442 (5) | C28—C29 | 1.550 (6) |
C15—C16 | 1.380 (5) | C28—H28A | 0.9700 |
C15—H15 | 0.9300 | C28—H28B | 0.9700 |
C16—N5 | 1.345 (5) | C29—C30 | 1.478 (6) |
C16—H16 | 0.9300 | C29—H29A | 0.9700 |
C6—N2 | 1.501 (5) | C29—H29B | 0.9700 |
C6—C7 | 1.539 (6) | C30—N11 | 1.177 (5) |
C6—H6A | 0.9700 | C31—N10 | 1.459 (5) |
C6—H6B | 0.9700 | C31—C32 | 1.553 (6) |
C7—C8 | 1.476 (7) | C31—H31A | 0.9700 |
C7—H7A | 0.9700 | C31—H31B | 0.9700 |
C7—H7B | 0.9700 | C32—C33 | 1.452 (6) |
C8—N3 | 1.141 (6) | C32—H32A | 0.9700 |
C9—N2 | 1.481 (5) | C32—H32B | 0.9700 |
C9—C10 | 1.525 (6) | C33—N12 | 1.155 (5) |
C9—H9A | 0.9600 | C39—N14 | 1.473 (5) |
C9—H9B | 0.9601 | C39—C40 | 1.526 (6) |
C10—C11 | 1.481 (6) | C39—H39A | 0.9700 |
C10—H10A | 0.9700 | C39—H39B | 0.9700 |
C10—H10B | 0.9700 | C40—C41 | 1.517 (7) |
C11—N4 | 1.128 (5) | C40—H40A | 0.9700 |
C17—N6 | 1.490 (5) | C40—H40B | 0.9700 |
C17—C18 | 1.570 (5) | C41—N15 | 1.123 (6) |
C17—H17A | 0.9700 | C42—N14 | 1.499 (5) |
C17—H17B | 0.9700 | C42—C43 | 1.533 (6) |
C18—C19 | 1.492 (7) | C42—H42A | 0.9700 |
C18—H18A | 0.9700 | C42—H42B | 0.9700 |
C18—H18B | 0.9700 | C43—C44 | 1.436 (7) |
C19—N7 | 1.131 (6) | C43—H43A | 0.9700 |
C20—N6 | 1.475 (5) | C43—H43B | 0.9700 |
C20—C21 | 1.550 (5) | C44—N16 | 1.152 (6) |
C20—H20A | 0.9700 | Cl2—O6 | 1.396 (3) |
C20—H20B | 0.9700 | Cl2—O8 | 1.426 (3) |
C21—C22 | 1.475 (6) | Cl2—O7 | 1.454 (4) |
C21—H21A | 0.9700 | Cl2—O5 | 1.460 (3) |
C21—H21B | 0.9700 | Cl1—O2 | 1.429 (3) |
C22—N8 | 1.122 (5) | Cl1—O3 | 1.444 (3) |
C23—N9 | 1.343 (5) | Cl1—O4 | 1.452 (3) |
C23—C24 | 1.409 (5) | Cl1—O1 | 1.460 (3) |
N1—Ag1—N5 | 179.10 (13) | C35—C34—H34 | 117.1 |
N9—Ag2—N13 | 177.12 (13) | C34—C35—C36 | 119.2 (4) |
N1—C1—C2 | 124.4 (4) | C34—C35—H35 | 120.4 |
N1—C1—H1 | 117.8 | C36—C35—H35 | 120.4 |
C2—C1—H1 | 117.8 | N14—C36—C35 | 124.2 (4) |
C1—C2—C3 | 119.5 (4) | N14—C36—C37 | 121.5 (3) |
C1—C2—H2 | 120.2 | C35—C36—C37 | 114.3 (3) |
C3—C2—H2 | 120.2 | C38—C37—C36 | 119.5 (4) |
N2—C3—C4 | 122.7 (4) | C38—C37—H37 | 120.2 |
N2—C3—C2 | 120.9 (3) | C36—C37—H37 | 120.2 |
C4—C3—C2 | 116.3 (4) | N13—C38—C37 | 125.3 (4) |
C5—C4—C3 | 119.7 (4) | N13—C38—H38 | 117.3 |
C5—C4—H4 | 120.1 | C37—C38—H38 | 117.3 |
C3—C4—H4 | 120.1 | N10—C28—C29 | 111.1 (3) |
N1—C5—C4 | 123.9 (4) | N10—C28—H28A | 109.4 |
N1—C5—H5 | 118.1 | C29—C28—H28A | 109.4 |
C4—C5—H5 | 118.1 | N10—C28—H28B | 109.4 |
N5—C12—C13 | 124.2 (4) | C29—C28—H28B | 109.4 |
N5—C12—H12 | 117.9 | H28A—C28—H28B | 108.0 |
C13—C12—H12 | 117.9 | C30—C29—C28 | 110.9 (4) |
C12—C13—C14 | 121.8 (4) | C30—C29—H29A | 109.5 |
C12—C13—H13 | 119.1 | C28—C29—H29A | 109.5 |
C14—C13—H13 | 119.1 | C30—C29—H29B | 109.5 |
N6—C14—C13 | 125.1 (3) | C28—C29—H29B | 109.5 |
N6—C14—C15 | 120.8 (3) | H29A—C29—H29B | 108.1 |
C13—C14—C15 | 114.1 (3) | N11—C30—C29 | 178.7 (4) |
C16—C15—C14 | 119.2 (4) | N10—C31—C32 | 112.9 (3) |
C16—C15—H15 | 120.4 | N10—C31—H31A | 109.0 |
C14—C15—H15 | 120.4 | C32—C31—H31A | 109.0 |
N5—C16—C15 | 125.7 (4) | N10—C31—H31B | 109.0 |
N5—C16—H16 | 117.2 | C32—C31—H31B | 109.0 |
C15—C16—H16 | 117.2 | H31A—C31—H31B | 107.8 |
N2—C6—C7 | 110.3 (3) | C33—C32—C31 | 111.1 (4) |
N2—C6—H6A | 109.6 | C33—C32—H32A | 109.4 |
C7—C6—H6A | 109.6 | C31—C32—H32A | 109.4 |
N2—C6—H6B | 109.6 | C33—C32—H32B | 109.4 |
C7—C6—H6B | 109.6 | C31—C32—H32B | 109.4 |
H6A—C6—H6B | 108.1 | H32A—C32—H32B | 108.0 |
C8—C7—C6 | 109.8 (4) | N12—C33—C32 | 177.6 (5) |
C8—C7—H7A | 109.7 | N14—C39—C40 | 111.9 (4) |
C6—C7—H7A | 109.7 | N14—C39—H39A | 109.2 |
C8—C7—H7B | 109.7 | C40—C39—H39A | 109.2 |
C6—C7—H7B | 109.7 | N14—C39—H39B | 109.2 |
H7A—C7—H7B | 108.2 | C40—C39—H39B | 109.2 |
N3—C8—C7 | 177.1 (6) | H39A—C39—H39B | 107.9 |
N2—C9—C10 | 115.7 (3) | C41—C40—C39 | 111.3 (4) |
N2—C9—H9A | 112.2 | C41—C40—H40A | 109.4 |
C10—C9—H9A | 123.1 | C39—C40—H40A | 109.4 |
N2—C9—H9B | 111.2 | C41—C40—H40B | 109.4 |
C10—C9—H9B | 79.8 | C39—C40—H40B | 109.4 |
H9A—C9—H9B | 109.5 | H40A—C40—H40B | 108.0 |
C11—C10—C9 | 115.4 (4) | N15—C41—C40 | 176.9 (6) |
C11—C10—H10A | 108.4 | N14—C42—C43 | 115.0 (3) |
C9—C10—H10A | 108.4 | N14—C42—H42A | 108.5 |
C11—C10—H10B | 108.4 | C43—C42—H42A | 108.5 |
C9—C10—H10B | 108.4 | N14—C42—H42B | 108.5 |
H10A—C10—H10B | 107.5 | C43—C42—H42B | 108.5 |
N4—C11—C10 | 178.9 (5) | H42A—C42—H42B | 107.5 |
N6—C17—C18 | 113.7 (3) | C44—C43—C42 | 112.8 (4) |
N6—C17—H17A | 108.8 | C44—C43—H43A | 109.0 |
C18—C17—H17A | 108.8 | C42—C43—H43A | 109.0 |
N6—C17—H17B | 108.8 | C44—C43—H43B | 109.0 |
C18—C17—H17B | 108.8 | C42—C43—H43B | 109.0 |
H17A—C17—H17B | 107.7 | H43A—C43—H43B | 107.8 |
C19—C18—C17 | 112.8 (4) | N16—C44—C43 | 179.2 (5) |
C19—C18—H18A | 109.0 | C1—N1—C5 | 116.1 (3) |
C17—C18—H18A | 109.0 | C1—N1—Ag1 | 123.1 (3) |
C19—C18—H18B | 109.0 | C5—N1—Ag1 | 120.7 (3) |
C17—C18—H18B | 109.0 | C3—N2—C9 | 120.4 (3) |
H18A—C18—H18B | 107.8 | C3—N2—C6 | 121.3 (3) |
N7—C19—C18 | 177.8 (5) | C9—N2—C6 | 118.1 (3) |
N6—C20—C21 | 114.1 (3) | C16—N5—C12 | 115.0 (3) |
N6—C20—H20A | 108.7 | C16—N5—Ag1 | 122.3 (3) |
C21—C20—H20A | 108.7 | C12—N5—Ag1 | 122.6 (3) |
N6—C20—H20B | 108.7 | C14—N6—C20 | 121.2 (3) |
C21—C20—H20B | 108.7 | C14—N6—C17 | 123.0 (3) |
H20A—C20—H20B | 107.6 | C20—N6—C17 | 115.7 (3) |
C22—C21—C20 | 114.5 (4) | C23—N9—C27 | 115.7 (3) |
C22—C21—H21A | 108.6 | C23—N9—Ag2 | 120.0 (3) |
C20—C21—H21A | 108.6 | C27—N9—Ag2 | 123.1 (3) |
C22—C21—H21B | 108.6 | C25—N10—C31 | 123.0 (3) |
C20—C21—H21B | 108.6 | C25—N10—C28 | 122.2 (3) |
H21A—C21—H21B | 107.6 | C31—N10—C28 | 114.0 (3) |
N8—C22—C21 | 177.3 (6) | C34—N13—C38 | 115.7 (3) |
N9—C23—C24 | 125.3 (4) | C34—N13—Ag2 | 122.7 (3) |
N9—C23—H23 | 117.3 | C38—N13—Ag2 | 121.6 (3) |
C24—C23—H23 | 117.3 | C36—N14—C39 | 121.2 (3) |
C23—C24—C25 | 117.7 (4) | C36—N14—C42 | 121.4 (3) |
C23—C24—H24 | 121.2 | C39—N14—C42 | 117.3 (3) |
C25—C24—H24 | 121.2 | O6—Cl2—O8 | 111.7 (2) |
N10—C25—C26 | 123.8 (4) | O6—Cl2—O7 | 113.3 (2) |
N10—C25—C24 | 119.9 (3) | O8—Cl2—O7 | 107.0 (2) |
C26—C25—C24 | 116.3 (3) | O6—Cl2—O5 | 110.2 (2) |
C27—C26—C25 | 119.6 (4) | O8—Cl2—O5 | 108.9 (2) |
C27—C26—H26 | 120.2 | O7—Cl2—O5 | 105.5 (2) |
C25—C26—H26 | 120.2 | O2—Cl1—O3 | 110.53 (18) |
N9—C27—C26 | 125.2 (4) | O2—Cl1—O4 | 110.23 (18) |
N9—C27—H27 | 117.4 | O3—Cl1—O4 | 108.47 (17) |
C26—C27—H27 | 117.4 | O2—Cl1—O1 | 109.70 (17) |
N13—C34—C35 | 125.8 (4) | O3—Cl1—O1 | 108.84 (18) |
N13—C34—H34 | 117.1 | O4—Cl1—O1 | 109.04 (17) |
N1—C1—C2—C3 | −0.8 (7) | C10—C9—N2—C3 | 97.1 (5) |
C1—C2—C3—N2 | 177.7 (4) | C10—C9—N2—C6 | −88.6 (4) |
C1—C2—C3—C4 | −0.3 (6) | C7—C6—N2—C3 | −84.7 (5) |
N2—C3—C4—C5 | −177.3 (4) | C7—C6—N2—C9 | 101.0 (4) |
C2—C3—C4—C5 | 0.7 (6) | C15—C16—N5—C12 | −2.4 (6) |
C3—C4—C5—N1 | 0.0 (6) | C15—C16—N5—Ag1 | 173.1 (3) |
N5—C12—C13—C14 | 1.5 (6) | C13—C12—N5—C16 | 0.9 (5) |
C12—C13—C14—N6 | 177.9 (4) | C13—C12—N5—Ag1 | −174.6 (3) |
C12—C13—C14—C15 | −2.4 (5) | C13—C14—N6—C20 | 9.2 (6) |
N6—C14—C15—C16 | −179.3 (3) | C15—C14—N6—C20 | −170.4 (3) |
C13—C14—C15—C16 | 1.1 (5) | C13—C14—N6—C17 | −165.4 (3) |
C14—C15—C16—N5 | 1.4 (6) | C15—C14—N6—C17 | 15.0 (5) |
N2—C6—C7—C8 | 179.7 (4) | C21—C20—N6—C14 | −96.1 (4) |
N2—C9—C10—C11 | −66.3 (5) | C21—C20—N6—C17 | 78.8 (4) |
N6—C17—C18—C19 | 78.6 (5) | C18—C17—N6—C14 | −101.7 (4) |
N6—C20—C21—C22 | 74.1 (5) | C18—C17—N6—C20 | 83.5 (4) |
N9—C23—C24—C25 | 0.6 (6) | C24—C23—N9—C27 | −1.5 (6) |
C23—C24—C25—N10 | −178.0 (4) | C24—C23—N9—Ag2 | 166.3 (3) |
C23—C24—C25—C26 | 1.9 (5) | C26—C27—N9—C23 | −0.2 (6) |
N10—C25—C26—C27 | 176.5 (4) | C26—C27—N9—Ag2 | −167.6 (3) |
C24—C25—C26—C27 | −3.4 (6) | C26—C25—N10—C31 | −165.0 (4) |
C25—C26—C27—N9 | 2.7 (6) | C24—C25—N10—C31 | 14.9 (6) |
N13—C34—C35—C36 | −3.4 (7) | C26—C25—N10—C28 | 4.0 (6) |
C34—C35—C36—N14 | −179.2 (4) | C24—C25—N10—C28 | −176.1 (4) |
C34—C35—C36—C37 | 0.7 (6) | C32—C31—N10—C25 | −94.3 (5) |
N14—C36—C37—C38 | −179.9 (4) | C32—C31—N10—C28 | 95.9 (4) |
C35—C36—C37—C38 | 0.2 (6) | C29—C28—N10—C25 | −84.5 (4) |
C36—C37—C38—N13 | 1.2 (7) | C29—C28—N10—C31 | 85.4 (4) |
N10—C28—C29—C30 | −168.5 (3) | C35—C34—N13—C38 | 4.6 (7) |
N10—C31—C32—C33 | −173.9 (3) | C35—C34—N13—Ag2 | −175.5 (3) |
N14—C39—C40—C41 | −179.8 (4) | C37—C38—N13—C34 | −3.5 (7) |
N14—C42—C43—C44 | 64.4 (5) | C37—C38—N13—Ag2 | 176.6 (3) |
C2—C1—N1—C5 | 1.5 (6) | C35—C36—N14—C39 | 179.3 (4) |
C2—C1—N1—Ag1 | −174.1 (3) | C37—C36—N14—C39 | −0.6 (6) |
C4—C5—N1—C1 | −1.1 (6) | C35—C36—N14—C42 | 2.3 (6) |
C4—C5—N1—Ag1 | 174.7 (3) | C37—C36—N14—C42 | −177.6 (4) |
C4—C3—N2—C9 | −3.2 (6) | C40—C39—N14—C36 | 79.6 (5) |
C2—C3—N2—C9 | 178.9 (4) | C40—C39—N14—C42 | −103.2 (4) |
C4—C3—N2—C6 | −177.3 (4) | C43—C42—N14—C36 | −101.7 (5) |
C2—C3—N2—C6 | 4.8 (6) | C43—C42—N14—C39 | 81.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N4i | 0.93 | 2.59 | 3.365 (6) | 142 |
C10—H10A···N11ii | 0.97 | 2.52 | 3.362 (6) | 145 |
C10—H10B···O3 | 0.97 | 2.57 | 3.346 (5) | 137 |
C10—H10B···N15i | 0.97 | 2.57 | 3.267 (6) | 129 |
C17—H17A···O7iii | 0.97 | 2.52 | 3.305 (5) | 138 |
C29—H29A···O4ii | 0.97 | 2.51 | 3.307 (5) | 140 |
C29—H29B···N8i | 0.97 | 2.68 | 3.329 (6) | 125 |
C32—H32B···O4iv | 0.97 | 2.61 | 3.279 (5) | 127 |
C32—H32B···N7v | 0.97 | 2.83 | 3.474 (6) | 125 |
C34—H34···O7vi | 0.93 | 2.59 | 3.405 (5) | 147 |
C35—H35···N16v | 0.93 | 2.54 | 3.382 (6) | 151 |
C38—H38···O2 | 0.93 | 2.53 | 3.446 (5) | 168 |
C40—H40A···N4 | 0.97 | 2.59 | 3.380 (6) | 138 |
C43—H43A···N3v | 0.97 | 2.62 | 3.457 (7) | 145 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z−1; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y+2, −z+1; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C11H12N4)2](ClO4) |
Mr | 607.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.221 (2), 14.457 (2), 19.897 (2) |
α, β, γ (°) | 76.39 (1), 84.20 (1), 88.06 (1) |
V (Å3) | 2564.6 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.94 |
Crystal size (mm) | 0.3 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Bruker Smart Apex CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) SADABS; Bruker, 2000 |
Tmin, Tmax | 0.762, 0.827 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13111, 8825, 6422 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.103, 1.05 |
No. of reflections | 8825 |
No. of parameters | 601 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.83, −0.98 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
Ag1—N1 | 2.139 (3) | Cl2—O7 | 1.454 (4) |
Ag1—N5 | 2.139 (3) | Cl2—O5 | 1.460 (3) |
Ag2—N9 | 2.138 (3) | Cl1—O2 | 1.429 (3) |
Ag2—N13 | 2.142 (3) | Cl1—O3 | 1.444 (3) |
Cl2—O6 | 1.396 (3) | Cl1—O4 | 1.452 (3) |
Cl2—O8 | 1.426 (3) | Cl1—O1 | 1.460 (3) |
N1—Ag1—N5 | 179.10 (13) | N9—Ag2—N13 | 177.12 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N4i | 0.93 | 2.59 | 3.365 (6) | 141.5 |
C10—H10A···N11ii | 0.97 | 2.52 | 3.362 (6) | 144.5 |
C10—H10B···O3 | 0.97 | 2.57 | 3.346 (5) | 136.9 |
C10—H10B···N15i | 0.97 | 2.57 | 3.267 (6) | 129.4 |
C17—H17A···O7iii | 0.97 | 2.52 | 3.305 (5) | 137.5 |
C29—H29A···O4ii | 0.97 | 2.51 | 3.307 (5) | 139.6 |
C29—H29B···N8i | 0.97 | 2.68 | 3.329 (6) | 125.0 |
C32—H32B···O4iv | 0.97 | 2.61 | 3.279 (5) | 126.5 |
C32—H32B···N7v | 0.97 | 2.83 | 3.474 (6) | 124.8 |
C34—H34···O7vi | 0.93 | 2.59 | 3.405 (5) | 147.2 |
C35—H35···N16v | 0.93 | 2.54 | 3.382 (6) | 151.4 |
C38—H38···O2 | 0.93 | 2.53 | 3.446 (5) | 167.7 |
C40—H40A···N4 | 0.97 | 2.59 | 3.380 (6) | 138.2 |
C43—H43A···N3v | 0.97 | 2.62 | 3.457 (7) | 144.9 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z−1; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y+2, −z+1; (vi) x+1, y, z. |
Recently, a series of compounds with zeolite-like molecular-sized channels, pores and cavities have been attracting considerable attention (Bowes et al., 1996; Kitazawa et al., 1992; Martin et al., 1998). These compounds can bind many molecules into their cavities, which gives them unique properties as catalysts, as ion-exchangers, for molecular separation sorption, etc. (Behrens et al., 1997; Fujita et al., 1994; Hoelderich et al., 1988). The cavities are constructed by organic components as well as by coordination polymers. Clearly, molecular recognition and self-organization are important factors in the sorbing of the guest (Ducharme et al., 1988; Endo et al., 1995; Geib et al., 1991). It has been found that hydrogen-bonding interactions are very important for molecular recognition in a wide variety of crystal-packing configurations (Bishop et al., 1993; Hunter, 1994; Smith, 1998; Zaworotko, 1994). Silver is an important element, with abundant catalytic properties. Absorbed oxygen on the silver surface is well known in the catalysis of epoxide fomation and oxidative coupling of methane (Epling et al., 1997; Minahan et al., 1996; Serafin et al., 1998). Silver complexes have also been well documented as catalysts in many reactions, such as enantioselective alkylation of imino easter (Ferraris et al., 2002) and the hetero-Diels-Alder reaction (Hague et al., 2001). In this paper, we report the synthesis of the title compound, (I), which shows a two-dimensional layer structure.
The unit cell of (I) consists of two types of basic units that have the same chemical composition but crystallographically non-equivalent conformation. Each unit contains an Ag(CEAP)2+ cation and a ClO4− anion, and they form a vaulted structure. In the cation, each Ag atom is coordinated by two N atoms in the pyridine rings of two ligands, with Ag—N distances in the range 2.138 (3)–2.142 (3) Å and N—Ag—N angles of 179.1 (1)° in unit (a) and 177.1 (1)° in unit (b). The bond distances and angles are all within the range typically observed in Ag complexes (Furuta et al., 1999; Ozutsumi et al., 1997; Smith et al., 1999). The Cl—O distances in the two units are 1.396 (3)–1.460 (3) Å, which are also within the typical range (Riera et al., 1998). The dramatic difference between units (a) and (b) is the dihedral angle of the ligands. In unit (a), which consists of the Ag1 complex and Cl1 perchlorate, the angle between the planes of the two pyridine rings of the ligand is 45.8 (2)°. But in unit (b), which consists of the Ag2 complex and Cl2 perchlorate, the two pyridine rings are nearly coplanar and the angle between their planes is 16.7 (2)°. The complex packing consists of parallel layers. In one layer, all arc-centers of the vaulted cations have the same positions, and they stack above or below the plane. The two adjacent layers form a zip-like structure, and they are connected via? C—H···N hydrogen bonds (C4—H4···N4i, C40—H40A···N4, C35—H35···N16v; Table 2). We also found that neighboring layers slide laterally with respect to each other. The sliding of the layers and the vaulted structure of the Ag(CEAP)2+ cations make hydrogen-bond formation easy. In each layer, there are many chains composed of alternate? basic units, and the unit–unit distance (see Fig. 2 lu-u) in the chain is 8.893 (3) Å. All chains in the layer are parallel, with a chain–chain distance (see Fig. 2 lc-c) of 19.020 (2) Å. Neighboring chains also slide over each other, and they are connected? by C—H···N hydrogen bonds, with a C10···N11(1 − x, 1 − y, 2 − z) distance of 3.362 (6) Å. In a chain, the supramolecular cavites of the host are composed of adjacent units assembled through C—H···N hydrogen bonds. The length (see Fig. 2 lc) and width (see Fig.2 lu-u) of the cavity are 11.274 (2) and 8.893 (3) Å, respectively. All ClO4− anions are located as guests in the cavities and are connected to? the Ag(CEAP)2+ cations through C—H···O interactions. In unit (a), the ClO4− anion bridges three Ag(CEAP)2+ in the two layers to form a zip-like structure through C38—H38···O2, C10—H10B···O3 and C29—H29A···O4 (1 − x, 1 − y, 2 − z) hydrogen bonds. This anion also connects an adjacent zip structure, through the C32—H32B···O4 hydrogen bond. Therefore, the ClO4− anion in unit (a) bridges four Ag(CEAP)2+ cations to form a µ4-ClO4− bridging mode. In unit (b), the ClO4− anion bridges two Ag(CEAP)2+ cations with a µ2-ClO4− bridging mode (see Fig.3) to form a zip structure through C17—H17A···O7(1 + x, y, −1 + z) and C34—H34···O7(1 + x, y, z) hydrogen bonds. The O···H distances are in the range 2.51–2.59 Å, with C···O distances in the range 3.279 (5)–3.446 (5) Å, falling into the normal range of C—H···O separations (Desiraju, 1991; Steiner et al., 1998).