Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027079/zl2033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027079/zl2033Isup2.hkl |
CCDC reference: 654742
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.030
- wR factor = 0.079
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT410_ALERT_2_C Short Intra H...H Contact H43 .. H44B .. 1.95 Ang. PLAT411_ALERT_2_C Short Inter H...H Contact H10 .. H48C .. 2.13 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C16 .. C50A .. 3.18 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.44 Deg. AG1A -N1 -AG1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.92 Deg. AG1 -N2 -AG1A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.87 Deg. AG1 -N3 -AG1A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 7.17 Deg. AG1A -N4 -AG1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.30 Deg. C50A -C44 -C50 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.50 Deg. H44A -C44 -H44B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H54A -C45 -H54C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H54B -C45 -H54D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.90 Deg. C48A -C47 -C48 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.50 Deg. H47B -C47 -H47C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.80 Deg. H47A -C47 -H47D 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 14 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Amirnasr et al. (2006); Bowyer et al. (1998); Chakraborty et al. (1999); Dehghanpour (2007); Hannon et al. (1999).
To a solution of bis(cycloheptyl-pyridin-2-ylmethylene-amine) (37.8 mg, 0.1 mmol) in 20 ml acetonitrile was added silver tetraphenylborate (28.9 mg, 0.1 mmol). The mixture was heated to dissolve the reactants. The solution was filtered and the volume of solvent removed under vacuum to about 5 ml. The diffusion of diethyl ether vapor into the solution gave light-yellow crystals. The crystals were collected and washed with diethylether-dichloromethane (9:1 v/v); yield 85%. Calc. for C50H56AgBN4: C 72.21, H 6.79, N 6.74%; found: C 72.23, H 6.80, N 6.75%.
Hydrogen atoms were generated geometrically (C–H 0.93 to 1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 times Ueq(C). For Ag1, C48, C49, and C50, alternative positions indicating disorder could be refined in a split atom model with common site occupation factors of 0.127 (2). For the C—C bond lengths in this part restraints of 1.52 (1) Å with a standard deviation of 0.02 Å were used in the refinement. For Ag1 and Ag1a independent anisotropic displacement parameters could be refined, for the splitted C atoms common anisotropic parameters were used for both positions. The H-atom positions were calculated for both alternative conformations. Similar but less resolved disorder phenomena have been observed for a second crystal measured at 193 K.
Pyridinecarbaldehyde and its substituted derivatives condense with amines to furnish a range of diimine compounds; such compounds have been used as ligands of transition metals. Among such complexes whose structures have been described are, for example, compounds of copper(I) (Dehghanpour et al., 2007), silver(I) (Bowyer et al., 1998; Hannon et al., 1999) and Ru(II) (Chakraborty et al., 1999). The title complex, (I), was prepared by the reaction of AgBPh4 with the bidentate ligand N,N'-cycloheptyl-pyridin-2-ylmethylene-amine.
One of the cycloheptyl substituents proved to show disorder with an alternative conformation (shown bright transparent in figure 1a) occupied at 12.7 (2)%, which will be discussed in detail in the next paragraph. The general geometry for the complex is similar with either of the two alternative orientations. While a tetrahedral geometry might be expected for four coordinated silver(I), the coordination sphere around the metal ion in this complex is strongly distorted by the restricting bite angles of the chelating ligand. The intraligand N1–Ag1–N2 and N3–Ag1–N4 angles [72.93 (4), 73.05 (4) °] are much less than 109.5 °. On the contrary the N2–Ag1–N3 and N2–Ag1–N4 angles [148.72 (5), 137.23 (5) °] are much larger than those of a tetrahedral complex. Ag1 is only 0.1135 (5) Å above the plane of N2, N3, and N4, and the bond Ag1—N1 is inclined by 69.72 (3)° with respect to this plane. The Ag–N bond lengths are similar to the corresponding bond distances in related complexes (Amirnasr et al., 2006; Bowyer et al., 1998; Hannon et al., 1999). The dihedral angle between the two chelate rings is 87.06 (4) °. The environments of the imine and pyridine nitrogen atoms are planar with the sums of the three N atom bond angles being 360.0 ° and 359.9 ° for N1 and N2, respectively. Despite the fact that the nitrogen atom (N1) is sp2 hybridized, some strain in the chelate ring is suggested by the deviation from the 120 ° angle at nitrogen (C25–N1–C29 = 117.6 (1)°).
In the arrangement with the at N4 disordered cycloheptyl rest (bright transparent in figure 1a) the C50 methylene group is more remote of Ag1, the silver atom also moves out by 0.405 (5) Å toward an alternative position. Here the most obtuse angle changes from N2—Ag1—N3 (148.72 (4)°) to N2—Ag1a—N4 (152.8 (2)°), and Ag1 approaches N4. In both alternative conformations, the shortest Ag···H contacts are similar (Ag1···H33a 2.85 Å, Ag1···H50a 3.14 Å; Ag1a···H33a 2.90 Å, Ag1a···H49c 3.11 Å) and are close to the sum of the Van der Waals radii (2.92 Å). Apparently the coordinational compromise provoked by the geometrical restrictions of the chelate ligands may find different solutions with similar energy.
For related literature, see: Amirnasr et al. (2006); Bowyer et al. (1998); Chakraborty et al. (1999); Dehghanpour (2007); Hannon et al. (1999).
Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).
[Ag(C26H36N4)2]C24H20B | F(000) = 1744 |
Mr = 831.67 | Dx = 1.315 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 49514 reflections |
a = 13.2093 (3) Å | θ = 1.6–29.8° |
b = 15.2132 (2) Å | µ = 0.52 mm−1 |
c = 21.6851 (6) Å | T = 100 K |
β = 105.462 (2)° | Prism, light-yellow |
V = 4200.03 (16) Å3 | 0.50 × 0.38 × 0.24 mm |
Z = 4 |
Stoe IPDS II diffractometer | 11472 independent reflections |
Radiation source: fine-focus sealed tube | 10372 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 6.7 pixels mm-1 | θmax = 29.4°, θmin = 1.6° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (Blessing, 1995) | k = −21→20 |
Tmin = 0.781, Tmax = 0.886 | l = −28→29 |
32871 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0419P)2 + 1.6408P] where P = (Fo2 + 2Fc2)/3 |
11472 reflections | (Δ/σ)max = 0.003 |
524 parameters | Δρmax = 0.53 e Å−3 |
8 restraints | Δρmin = −0.58 e Å−3 |
[Ag(C26H36N4)2]C24H20B | V = 4200.03 (16) Å3 |
Mr = 831.67 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.2093 (3) Å | µ = 0.52 mm−1 |
b = 15.2132 (2) Å | T = 100 K |
c = 21.6851 (6) Å | 0.50 × 0.38 × 0.24 mm |
β = 105.462 (2)° |
Stoe IPDS II diffractometer | 11472 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 10372 reflections with I > 2σ(I) |
Tmin = 0.781, Tmax = 0.886 | Rint = 0.017 |
32871 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 8 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.53 e Å−3 |
11472 reflections | Δρmin = −0.58 e Å−3 |
524 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 | Occ. (<1) | |
B1 | 0.71523 (11) | 0.77457 (9) | 0.04699 (7) | 0.0190 (2) | |
C1 | 0.65428 (9) | 0.77615 (8) | 0.10404 (6) | 0.0193 (2) | |
C2 | 0.61436 (10) | 0.70078 (8) | 0.12635 (6) | 0.0212 (2) | |
H2 | 0.6256 | 0.6453 | 0.1091 | 0.025* | |
C3 | 0.55857 (10) | 0.70357 (9) | 0.17289 (6) | 0.0226 (2) | |
H3 | 0.5332 | 0.6506 | 0.1867 | 0.027* | |
C4 | 0.54016 (10) | 0.78309 (9) | 0.19895 (6) | 0.0224 (2) | |
H4 | 0.5020 | 0.7854 | 0.2304 | 0.027* | |
C5 | 0.57857 (9) | 0.85956 (9) | 0.17828 (6) | 0.0213 (2) | |
H5 | 0.5667 | 0.9147 | 0.1956 | 0.026* | |
C6 | 0.63446 (9) | 0.85551 (8) | 0.13219 (6) | 0.0205 (2) | |
H6 | 0.6604 | 0.9087 | 0.1192 | 0.025* | |
C7 | 0.82698 (10) | 0.83014 (8) | 0.06767 (6) | 0.0201 (2) | |
C8 | 0.87241 (10) | 0.86601 (9) | 0.12822 (6) | 0.0222 (2) | |
H8 | 0.8364 | 0.8597 | 0.1605 | 0.027* | |
C9 | 0.96835 (10) | 0.91059 (9) | 0.14326 (7) | 0.0259 (3) | |
H9 | 0.9958 | 0.9342 | 0.1849 | 0.031* | |
C10 | 1.02359 (10) | 0.92053 (9) | 0.09771 (7) | 0.0284 (3) | |
H10 | 1.0886 | 0.9511 | 0.1076 | 0.034* | |
C11 | 0.98216 (11) | 0.88498 (10) | 0.03731 (7) | 0.0280 (3) | |
H11 | 1.0193 | 0.8906 | 0.0056 | 0.034* | |
C12 | 0.88647 (10) | 0.84116 (9) | 0.02314 (7) | 0.0241 (2) | |
H12 | 0.8599 | 0.8175 | −0.0186 | 0.029* | |
C13 | 0.74120 (10) | 0.67239 (8) | 0.03106 (6) | 0.0202 (2) | |
C14 | 0.84116 (10) | 0.63461 (9) | 0.05230 (6) | 0.0224 (2) | |
H14 | 0.8974 | 0.6698 | 0.0762 | 0.027* | |
C15 | 0.86144 (11) | 0.54728 (9) | 0.03978 (7) | 0.0272 (3) | |
H15 | 0.9303 | 0.5241 | 0.0556 | 0.033* | |
C16 | 0.78187 (12) | 0.49443 (9) | 0.00444 (7) | 0.0284 (3) | |
H16 | 0.7955 | 0.4351 | −0.0044 | 0.034* | |
C17 | 0.68159 (12) | 0.52949 (9) | −0.01789 (7) | 0.0276 (3) | |
H17 | 0.6260 | 0.4941 | −0.0423 | 0.033* | |
C18 | 0.66253 (10) | 0.61634 (9) | −0.00446 (7) | 0.0245 (2) | |
H18 | 0.5933 | 0.6388 | −0.0200 | 0.029* | |
C19 | 0.63786 (10) | 0.81801 (8) | −0.01880 (6) | 0.0201 (2) | |
C20 | 0.65518 (11) | 0.80003 (9) | −0.07887 (6) | 0.0236 (2) | |
H20 | 0.7107 | 0.7612 | −0.0806 | 0.028* | |
C21 | 0.59516 (11) | 0.83618 (9) | −0.13563 (6) | 0.0264 (3) | |
H21 | 0.6111 | 0.8232 | −0.1749 | 0.032* | |
C22 | 0.51163 (11) | 0.89140 (9) | −0.13496 (7) | 0.0268 (3) | |
H22 | 0.4695 | 0.9160 | −0.1736 | 0.032* | |
C23 | 0.49090 (10) | 0.90999 (9) | −0.07703 (7) | 0.0268 (3) | |
H23 | 0.4338 | 0.9473 | −0.0759 | 0.032* | |
C24 | 0.55340 (10) | 0.87427 (9) | −0.02035 (6) | 0.0231 (2) | |
H24 | 0.5380 | 0.8887 | 0.0188 | 0.028* | |
Ag1 | 0.85288 (4) | 0.19026 (4) | 0.14911 (2) | 0.02404 (7) | 0.873 (2) |
Ag1A | 0.8437 (2) | 0.2153 (3) | 0.15095 (15) | 0.0248 (5) | 0.127 (2) |
N1 | 1.01864 (9) | 0.26352 (8) | 0.14765 (5) | 0.0261 (2) | |
N2 | 0.96308 (9) | 0.17026 (8) | 0.24404 (5) | 0.0224 (2) | |
N3 | 0.76931 (8) | 0.13463 (7) | 0.05138 (5) | 0.0215 (2) | |
N4 | 0.72043 (9) | 0.29027 (8) | 0.10113 (6) | 0.0240 (2) | |
C25 | 1.04846 (11) | 0.31078 (10) | 0.10380 (7) | 0.0276 (3) | |
H25 | 0.9986 | 0.3211 | 0.0639 | 0.033* | |
C26 | 1.14861 (11) | 0.34568 (9) | 0.11333 (7) | 0.0254 (3) | |
H26 | 1.1664 | 0.3797 | 0.0810 | 0.031* | |
C27 | 1.22166 (10) | 0.32969 (9) | 0.17092 (7) | 0.0243 (2) | |
H27 | 1.2911 | 0.3520 | 0.1787 | 0.029* | |
C28 | 1.19238 (10) | 0.28065 (9) | 0.21724 (6) | 0.0225 (2) | |
H28 | 1.2412 | 0.2686 | 0.2572 | 0.027* | |
C29 | 1.08999 (10) | 0.24949 (9) | 0.20387 (6) | 0.0220 (2) | |
C30 | 1.05590 (10) | 0.20018 (8) | 0.25325 (6) | 0.0223 (2) | |
H30 | 1.1050 | 0.1903 | 0.2935 | 0.027* | |
C31 | 0.93615 (10) | 0.12872 (9) | 0.29904 (6) | 0.0224 (2) | |
H31 | 1.0028 | 0.1082 | 0.3296 | 0.027* | |
C32 | 0.86636 (10) | 0.04840 (9) | 0.27667 (7) | 0.0261 (3) | |
H32A | 0.8799 | 0.0055 | 0.3123 | 0.031* | |
H32B | 0.8883 | 0.0206 | 0.2410 | 0.031* | |
C33 | 0.74781 (11) | 0.06488 (10) | 0.25437 (7) | 0.0282 (3) | |
H33A | 0.7351 | 0.1215 | 0.2310 | 0.034* | |
H33B | 0.7148 | 0.0179 | 0.2241 | 0.034* | |
C34 | 0.69492 (11) | 0.06756 (10) | 0.30913 (7) | 0.0283 (3) | |
H34A | 0.6180 | 0.0632 | 0.2905 | 0.034* | |
H34B | 0.7173 | 0.0149 | 0.3362 | 0.034* | |
C35 | 0.71723 (11) | 0.14850 (10) | 0.35198 (7) | 0.0277 (3) | |
H35A | 0.6832 | 0.1405 | 0.3871 | 0.033* | |
H35B | 0.6840 | 0.2000 | 0.3266 | 0.033* | |
C36 | 0.83336 (11) | 0.16900 (10) | 0.38129 (7) | 0.0274 (3) | |
H36A | 0.8690 | 0.1154 | 0.4024 | 0.033* | |
H36B | 0.8396 | 0.2148 | 0.4146 | 0.033* | |
C37 | 0.88903 (11) | 0.20085 (9) | 0.33188 (7) | 0.0254 (3) | |
H37A | 0.8381 | 0.2347 | 0.2986 | 0.031* | |
H37B | 0.9460 | 0.2416 | 0.3533 | 0.031* | |
C38 | 0.78747 (10) | 0.05777 (9) | 0.02625 (6) | 0.0241 (2) | |
H38 | 0.8369 | 0.0185 | 0.0522 | 0.029* | |
C39 | 0.73743 (11) | 0.03279 (9) | −0.03600 (7) | 0.0258 (3) | |
H39 | 0.7516 | −0.0227 | −0.0520 | 0.031* | |
C40 | 0.66676 (11) | 0.08999 (9) | −0.07412 (6) | 0.0257 (3) | |
H40 | 0.6321 | 0.0749 | −0.1171 | 0.031* | |
C41 | 0.64692 (10) | 0.16987 (9) | −0.04885 (6) | 0.0235 (2) | |
H41 | 0.5986 | 0.2104 | −0.0742 | 0.028* | |
C42 | 0.69887 (10) | 0.18943 (8) | 0.01403 (6) | 0.0206 (2) | |
C43 | 0.67639 (10) | 0.27201 (9) | 0.04304 (6) | 0.0231 (2) | |
H43 | 0.6279 | 0.3125 | 0.0178 | 0.028* | |
C44 | 0.69530 (11) | 0.37288 (9) | 0.12804 (7) | 0.0270 (3) | |
H44A | 0.6708 | 0.4165 | 0.0927 | 0.032* | 0.873 (2) |
H44B | 0.6503 | 0.3977 | 0.0872 | 0.032* | 0.127 (2) |
C45 | 0.60658 (11) | 0.35548 (9) | 0.15949 (7) | 0.0278 (3) | |
H54A | 0.5455 | 0.3316 | 0.1268 | 0.033* | 0.873 (2) |
H54B | 0.6300 | 0.3100 | 0.1929 | 0.033* | 0.873 (2) |
H54C | 0.5455 | 0.3316 | 0.1268 | 0.033* | 0.127 (2) |
H54D | 0.6300 | 0.3100 | 0.1929 | 0.033* | 0.127 (2) |
C46 | 0.57134 (13) | 0.43643 (10) | 0.18983 (8) | 0.0349 (3) | |
H46A | 0.5014 | 0.4247 | 0.1967 | 0.042* | |
H46B | 0.5639 | 0.4864 | 0.1597 | 0.042* | |
C47 | 0.64702 (17) | 0.46260 (11) | 0.25355 (8) | 0.0444 (4) | |
H47A | 0.6729 | 0.4082 | 0.2777 | 0.053* | 0.873 (2) |
H47B | 0.6071 | 0.4960 | 0.2785 | 0.053* | 0.873 (2) |
H47C | 0.6133 | 0.5117 | 0.2706 | 0.053* | 0.127 (2) |
H47D | 0.6499 | 0.4124 | 0.2830 | 0.053* | 0.127 (2) |
C48 | 0.74320 (17) | 0.51826 (15) | 0.24986 (9) | 0.0389 (4) | 0.873 (2) |
H48A | 0.7222 | 0.5809 | 0.2480 | 0.047* | 0.873 (2) |
H48B | 0.7985 | 0.5098 | 0.2904 | 0.047* | 0.873 (2) |
C49 | 0.79177 (14) | 0.50138 (11) | 0.19561 (10) | 0.0345 (4) | 0.873 (2) |
H49A | 0.8639 | 0.5258 | 0.2079 | 0.041* | 0.873 (2) |
H49B | 0.7514 | 0.5352 | 0.1581 | 0.041* | 0.873 (2) |
C50 | 0.79858 (12) | 0.40667 (10) | 0.17443 (8) | 0.0262 (3) | 0.873 (2) |
H50A | 0.8167 | 0.3684 | 0.2127 | 0.031* | 0.873 (2) |
H50B | 0.8560 | 0.4019 | 0.1531 | 0.031* | 0.873 (2) |
C50A | 0.7656 (8) | 0.4468 (6) | 0.1444 (5) | 0.0262 (3) | 0.127 (2) |
H50C | 0.7273 | 0.5025 | 0.1308 | 0.031* | 0.127 (2) |
H50D | 0.8231 | 0.4419 | 0.1232 | 0.031* | 0.127 (2) |
C49A | 0.8086 (9) | 0.4445 (8) | 0.2158 (5) | 0.0345 (4) | 0.127 (2) |
H49C | 0.8170 | 0.3817 | 0.2281 | 0.041* | 0.127 (2) |
H49D | 0.8802 | 0.4697 | 0.2254 | 0.041* | 0.127 (2) |
C48A | 0.7548 (8) | 0.4876 (10) | 0.2607 (7) | 0.0389 (4) | 0.127 (2) |
H48C | 0.7954 | 0.4743 | 0.3050 | 0.047* | 0.127 (2) |
H48D | 0.7573 | 0.5520 | 0.2549 | 0.047* | 0.127 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.0198 (6) | 0.0187 (6) | 0.0186 (6) | 0.0007 (5) | 0.0055 (5) | 0.0005 (5) |
C1 | 0.0166 (5) | 0.0217 (5) | 0.0184 (5) | 0.0013 (4) | 0.0025 (4) | 0.0011 (4) |
C2 | 0.0204 (5) | 0.0212 (5) | 0.0214 (6) | 0.0015 (4) | 0.0046 (4) | 0.0008 (4) |
C3 | 0.0202 (5) | 0.0246 (6) | 0.0231 (6) | −0.0009 (4) | 0.0058 (5) | 0.0034 (5) |
C4 | 0.0176 (5) | 0.0297 (6) | 0.0195 (5) | 0.0015 (4) | 0.0046 (4) | 0.0013 (5) |
C5 | 0.0183 (5) | 0.0242 (6) | 0.0202 (5) | 0.0020 (4) | 0.0032 (4) | −0.0016 (4) |
C6 | 0.0184 (5) | 0.0217 (5) | 0.0207 (5) | 0.0004 (4) | 0.0040 (4) | 0.0006 (4) |
C7 | 0.0201 (5) | 0.0180 (5) | 0.0224 (6) | 0.0023 (4) | 0.0060 (4) | 0.0016 (4) |
C8 | 0.0203 (5) | 0.0229 (6) | 0.0231 (6) | 0.0019 (4) | 0.0053 (4) | 0.0007 (5) |
C9 | 0.0210 (6) | 0.0269 (6) | 0.0274 (6) | 0.0003 (5) | 0.0024 (5) | −0.0033 (5) |
C10 | 0.0201 (6) | 0.0268 (6) | 0.0377 (7) | −0.0023 (5) | 0.0068 (5) | −0.0007 (6) |
C11 | 0.0241 (6) | 0.0298 (6) | 0.0334 (7) | −0.0009 (5) | 0.0132 (5) | 0.0001 (5) |
C12 | 0.0237 (6) | 0.0246 (6) | 0.0250 (6) | −0.0003 (5) | 0.0085 (5) | −0.0007 (5) |
C13 | 0.0222 (6) | 0.0212 (5) | 0.0178 (5) | 0.0007 (4) | 0.0064 (4) | 0.0015 (4) |
C14 | 0.0236 (6) | 0.0227 (6) | 0.0198 (5) | 0.0025 (4) | 0.0036 (4) | 0.0009 (4) |
C15 | 0.0299 (6) | 0.0249 (6) | 0.0266 (6) | 0.0077 (5) | 0.0071 (5) | 0.0031 (5) |
C16 | 0.0396 (7) | 0.0197 (6) | 0.0282 (7) | 0.0025 (5) | 0.0132 (6) | 0.0001 (5) |
C17 | 0.0330 (7) | 0.0234 (6) | 0.0266 (6) | −0.0046 (5) | 0.0084 (5) | −0.0026 (5) |
C18 | 0.0243 (6) | 0.0236 (6) | 0.0253 (6) | −0.0008 (5) | 0.0060 (5) | −0.0003 (5) |
C19 | 0.0201 (5) | 0.0201 (5) | 0.0199 (5) | −0.0012 (4) | 0.0049 (4) | 0.0016 (4) |
C20 | 0.0247 (6) | 0.0248 (6) | 0.0211 (6) | 0.0022 (5) | 0.0056 (5) | 0.0000 (5) |
C21 | 0.0303 (6) | 0.0277 (6) | 0.0199 (6) | −0.0018 (5) | 0.0046 (5) | 0.0007 (5) |
C22 | 0.0249 (6) | 0.0280 (6) | 0.0240 (6) | −0.0019 (5) | 0.0004 (5) | 0.0063 (5) |
C23 | 0.0203 (6) | 0.0283 (6) | 0.0310 (7) | 0.0032 (5) | 0.0053 (5) | 0.0061 (5) |
C24 | 0.0216 (5) | 0.0246 (6) | 0.0237 (6) | 0.0013 (4) | 0.0072 (5) | 0.0026 (5) |
Ag1 | 0.02016 (9) | 0.02887 (17) | 0.01943 (8) | −0.00104 (10) | −0.00109 (6) | 0.00182 (11) |
Ag1A | 0.0202 (6) | 0.0317 (12) | 0.0183 (5) | −0.0034 (8) | −0.0019 (4) | 0.0030 (8) |
N1 | 0.0232 (5) | 0.0343 (6) | 0.0197 (5) | −0.0017 (4) | 0.0038 (4) | 0.0028 (4) |
N2 | 0.0209 (5) | 0.0265 (5) | 0.0192 (5) | −0.0027 (4) | 0.0041 (4) | 0.0012 (4) |
N3 | 0.0193 (5) | 0.0232 (5) | 0.0207 (5) | −0.0001 (4) | 0.0029 (4) | 0.0021 (4) |
N4 | 0.0250 (5) | 0.0243 (5) | 0.0239 (5) | −0.0027 (4) | 0.0085 (4) | −0.0021 (4) |
C25 | 0.0273 (6) | 0.0350 (7) | 0.0199 (6) | 0.0002 (5) | 0.0055 (5) | 0.0039 (5) |
C26 | 0.0298 (6) | 0.0256 (6) | 0.0235 (6) | −0.0002 (5) | 0.0117 (5) | 0.0011 (5) |
C27 | 0.0230 (6) | 0.0249 (6) | 0.0269 (6) | −0.0019 (5) | 0.0100 (5) | −0.0020 (5) |
C28 | 0.0197 (5) | 0.0260 (6) | 0.0212 (6) | −0.0008 (4) | 0.0046 (4) | −0.0009 (5) |
C29 | 0.0213 (5) | 0.0253 (6) | 0.0194 (5) | −0.0007 (4) | 0.0056 (4) | 0.0001 (5) |
C30 | 0.0213 (6) | 0.0263 (6) | 0.0181 (5) | −0.0015 (4) | 0.0030 (4) | 0.0007 (4) |
C31 | 0.0189 (5) | 0.0274 (6) | 0.0200 (5) | −0.0028 (4) | 0.0035 (4) | 0.0025 (5) |
C32 | 0.0248 (6) | 0.0246 (6) | 0.0306 (7) | −0.0026 (5) | 0.0103 (5) | −0.0020 (5) |
C33 | 0.0240 (6) | 0.0316 (7) | 0.0282 (6) | −0.0085 (5) | 0.0056 (5) | −0.0048 (5) |
C34 | 0.0217 (6) | 0.0310 (7) | 0.0335 (7) | −0.0041 (5) | 0.0093 (5) | −0.0002 (6) |
C35 | 0.0245 (6) | 0.0292 (7) | 0.0314 (7) | 0.0013 (5) | 0.0110 (5) | 0.0022 (5) |
C36 | 0.0272 (6) | 0.0324 (7) | 0.0239 (6) | −0.0031 (5) | 0.0091 (5) | −0.0016 (5) |
C37 | 0.0256 (6) | 0.0263 (6) | 0.0248 (6) | −0.0056 (5) | 0.0074 (5) | −0.0018 (5) |
C38 | 0.0230 (6) | 0.0234 (6) | 0.0255 (6) | 0.0020 (4) | 0.0057 (5) | 0.0036 (5) |
C39 | 0.0294 (6) | 0.0218 (6) | 0.0280 (6) | −0.0018 (5) | 0.0107 (5) | −0.0019 (5) |
C40 | 0.0257 (6) | 0.0304 (6) | 0.0201 (6) | −0.0035 (5) | 0.0044 (5) | −0.0030 (5) |
C41 | 0.0217 (6) | 0.0280 (6) | 0.0189 (6) | 0.0003 (5) | 0.0023 (4) | 0.0015 (5) |
C42 | 0.0190 (5) | 0.0219 (5) | 0.0202 (6) | −0.0006 (4) | 0.0043 (4) | 0.0013 (4) |
C43 | 0.0230 (6) | 0.0232 (6) | 0.0227 (6) | 0.0012 (4) | 0.0055 (5) | 0.0018 (5) |
C44 | 0.0334 (7) | 0.0237 (6) | 0.0270 (6) | −0.0018 (5) | 0.0135 (5) | −0.0016 (5) |
C45 | 0.0282 (6) | 0.0254 (6) | 0.0329 (7) | −0.0010 (5) | 0.0134 (5) | −0.0004 (5) |
C46 | 0.0377 (8) | 0.0293 (7) | 0.0448 (9) | 0.0043 (6) | 0.0236 (7) | 0.0024 (6) |
C47 | 0.0813 (13) | 0.0296 (8) | 0.0296 (8) | 0.0048 (8) | 0.0272 (8) | −0.0001 (6) |
C48 | 0.0478 (10) | 0.0364 (11) | 0.0262 (9) | 0.0132 (8) | −0.0009 (7) | −0.0059 (8) |
C49 | 0.0322 (8) | 0.0241 (7) | 0.0437 (10) | −0.0002 (6) | 0.0042 (7) | −0.0069 (7) |
C50 | 0.0251 (7) | 0.0228 (7) | 0.0297 (8) | 0.0001 (5) | 0.0056 (6) | −0.0034 (6) |
C50A | 0.0251 (7) | 0.0228 (7) | 0.0297 (8) | 0.0001 (5) | 0.0056 (6) | −0.0034 (6) |
C49A | 0.0322 (8) | 0.0241 (7) | 0.0437 (10) | −0.0002 (6) | 0.0042 (7) | −0.0069 (7) |
C48A | 0.0478 (10) | 0.0364 (11) | 0.0262 (9) | 0.0132 (8) | −0.0009 (7) | −0.0059 (8) |
B1—C1 | 1.6463 (18) | C28—C29 | 1.3890 (17) |
B1—C13 | 1.6483 (18) | C28—H28 | 0.9500 |
B1—C19 | 1.6550 (19) | C29—C30 | 1.4728 (17) |
B1—C7 | 1.6558 (19) | C30—H30 | 0.9500 |
C1—C2 | 1.4009 (17) | C31—C37 | 1.5281 (19) |
C1—C6 | 1.4086 (17) | C31—C32 | 1.5296 (18) |
C2—C3 | 1.4002 (18) | C31—H31 | 1.0000 |
C2—H2 | 0.9500 | C32—C33 | 1.5314 (19) |
C3—C4 | 1.3839 (19) | C32—H32A | 0.9900 |
C3—H3 | 0.9500 | C32—H32B | 0.9900 |
C4—C5 | 1.3902 (18) | C33—C34 | 1.5305 (19) |
C4—H4 | 0.9500 | C33—H33A | 0.9900 |
C5—C6 | 1.3934 (17) | C33—H33B | 0.9900 |
C5—H5 | 0.9500 | C34—C35 | 1.523 (2) |
C6—H6 | 0.9500 | C34—H34A | 0.9900 |
C7—C8 | 1.4006 (18) | C34—H34B | 0.9900 |
C7—C12 | 1.4081 (17) | C35—C36 | 1.528 (2) |
C8—C9 | 1.3972 (18) | C35—H35A | 0.9900 |
C8—H8 | 0.9500 | C35—H35B | 0.9900 |
C9—C10 | 1.384 (2) | C36—C37 | 1.5309 (19) |
C9—H9 | 0.9500 | C36—H36A | 0.9900 |
C10—C11 | 1.388 (2) | C36—H36B | 0.9900 |
C10—H10 | 0.9500 | C37—H37A | 0.9900 |
C11—C12 | 1.3891 (18) | C37—H37B | 0.9900 |
C11—H11 | 0.9500 | C38—C39 | 1.3885 (19) |
C12—H12 | 0.9500 | C38—H38 | 0.9500 |
C13—C14 | 1.4006 (17) | C39—C40 | 1.3786 (19) |
C13—C18 | 1.4049 (18) | C39—H39 | 0.9500 |
C14—C15 | 1.3961 (18) | C40—C41 | 1.3866 (19) |
C14—H14 | 0.9500 | C40—H40 | 0.9500 |
C15—C16 | 1.382 (2) | C41—C42 | 1.3854 (18) |
C15—H15 | 0.9500 | C41—H41 | 0.9500 |
C16—C17 | 1.390 (2) | C42—C43 | 1.4705 (18) |
C16—H16 | 0.9500 | C43—H43 | 0.9500 |
C17—C18 | 1.3904 (19) | C44—C50A | 1.441 (7) |
C17—H17 | 0.9500 | C44—C45 | 1.5279 (18) |
C18—H18 | 0.9500 | C44—C50 | 1.551 (2) |
C19—C24 | 1.3995 (17) | C44—H44A | 1.0000 |
C19—C20 | 1.4082 (18) | C44—H44B | 1.0000 |
C20—C21 | 1.3876 (19) | C45—C46 | 1.526 (2) |
C20—H20 | 0.9500 | C45—H54A | 0.9900 |
C21—C22 | 1.390 (2) | C45—H54B | 0.9900 |
C21—H21 | 0.9500 | C45—H54C | 0.9900 |
C22—C23 | 1.384 (2) | C45—H54D | 0.9900 |
C22—H22 | 0.9500 | C46—C47 | 1.527 (3) |
C23—C24 | 1.3951 (18) | C46—H46A | 0.9900 |
C23—H23 | 0.9500 | C46—H46B | 0.9900 |
C24—H24 | 0.9500 | C47—C48A | 1.441 (9) |
Ag1—N2 | 2.2025 (12) | C47—C48 | 1.547 (3) |
Ag1—N3 | 2.2757 (12) | C47—H47A | 0.9900 |
Ag1—N4 | 2.3426 (13) | C47—H47B | 0.9900 |
Ag1—N1 | 2.4646 (12) | C47—H47C | 0.9899 |
Ag1A—N4 | 2.045 (4) | C47—H47D | 0.9899 |
Ag1A—N2 | 2.310 (3) | C48—C49 | 1.505 (3) |
Ag1A—N1 | 2.444 (3) | C48—H48A | 0.9900 |
Ag1A—N3 | 2.449 (4) | C48—H48B | 0.9900 |
N1—C25 | 1.3327 (18) | C49—C50 | 1.522 (2) |
N1—C29 | 1.3444 (17) | C49—H49A | 0.9900 |
N2—C30 | 1.2728 (17) | C49—H49B | 0.9900 |
N2—C31 | 1.4746 (16) | C50—H50A | 0.9900 |
N3—C38 | 1.3386 (17) | C50—H50B | 0.9900 |
N3—C42 | 1.3472 (16) | C50A—C49A | 1.501 (9) |
N4—C43 | 1.2695 (17) | C50A—H50C | 0.9900 |
N4—C44 | 1.4606 (17) | C50A—H50D | 0.9900 |
C25—C26 | 1.389 (2) | C49A—C48A | 1.500 (9) |
C25—H25 | 0.9500 | C49A—H49C | 0.9900 |
C26—C27 | 1.381 (2) | C49A—H49D | 0.9900 |
C26—H26 | 0.9500 | C48A—H48C | 0.9900 |
C27—C28 | 1.3866 (18) | C48A—H48D | 0.9900 |
C27—H27 | 0.9500 | ||
C1—B1—C13 | 110.00 (10) | H32A—C32—H32B | 107.3 |
C1—B1—C19 | 109.19 (10) | C34—C33—C32 | 113.54 (12) |
C13—B1—C19 | 108.13 (10) | C34—C33—H33A | 108.9 |
C1—B1—C7 | 111.61 (10) | C32—C33—H33A | 108.9 |
C13—B1—C7 | 108.54 (10) | C34—C33—H33B | 108.9 |
C19—B1—C7 | 109.31 (10) | C32—C33—H33B | 108.9 |
C2—C1—C6 | 114.91 (11) | H33A—C33—H33B | 107.7 |
C2—C1—B1 | 123.51 (11) | C35—C34—C33 | 116.15 (11) |
C6—C1—B1 | 121.52 (11) | C35—C34—H34A | 108.2 |
C3—C2—C1 | 122.90 (12) | C33—C34—H34A | 108.2 |
C3—C2—H2 | 118.6 | C35—C34—H34B | 108.2 |
C1—C2—H2 | 118.6 | C33—C34—H34B | 108.2 |
C4—C3—C2 | 120.28 (12) | H34A—C34—H34B | 107.4 |
C4—C3—H3 | 119.9 | C34—C35—C36 | 115.36 (12) |
C2—C3—H3 | 119.9 | C34—C35—H35A | 108.4 |
C3—C4—C5 | 118.75 (12) | C36—C35—H35A | 108.4 |
C3—C4—H4 | 120.6 | C34—C35—H35B | 108.4 |
C5—C4—H4 | 120.6 | C36—C35—H35B | 108.4 |
C4—C5—C6 | 120.20 (12) | H35A—C35—H35B | 107.5 |
C4—C5—H5 | 119.9 | C35—C36—C37 | 112.94 (12) |
C6—C5—H5 | 119.9 | C35—C36—H36A | 109.0 |
C5—C6—C1 | 122.96 (12) | C37—C36—H36A | 109.0 |
C5—C6—H6 | 118.5 | C35—C36—H36B | 109.0 |
C1—C6—H6 | 118.5 | C37—C36—H36B | 109.0 |
C8—C7—C12 | 114.75 (11) | H36A—C36—H36B | 107.8 |
C8—C7—B1 | 125.52 (11) | C31—C37—C36 | 115.48 (11) |
C12—C7—B1 | 119.69 (11) | C31—C37—H37A | 108.4 |
C9—C8—C7 | 122.90 (12) | C36—C37—H37A | 108.4 |
C9—C8—H8 | 118.5 | C31—C37—H37B | 108.4 |
C7—C8—H8 | 118.5 | C36—C37—H37B | 108.4 |
C10—C9—C8 | 120.30 (13) | H37A—C37—H37B | 107.5 |
C10—C9—H9 | 119.9 | N3—C38—C39 | 122.99 (12) |
C8—C9—H9 | 119.9 | N3—C38—H38 | 118.5 |
C9—C10—C11 | 118.74 (12) | C39—C38—H38 | 118.5 |
C9—C10—H10 | 120.6 | C40—C39—C38 | 118.75 (12) |
C11—C10—H10 | 120.6 | C40—C39—H39 | 120.6 |
C10—C11—C12 | 120.17 (13) | C38—C39—H39 | 120.6 |
C10—C11—H11 | 119.9 | C39—C40—C41 | 119.04 (12) |
C12—C11—H11 | 119.9 | C39—C40—H40 | 120.5 |
C11—C12—C7 | 123.14 (13) | C41—C40—H40 | 120.5 |
C11—C12—H12 | 118.4 | C42—C41—C40 | 118.75 (12) |
C7—C12—H12 | 118.4 | C42—C41—H41 | 120.6 |
C14—C13—C18 | 115.21 (12) | C40—C41—H41 | 120.6 |
C14—C13—B1 | 123.28 (11) | N3—C42—C41 | 122.71 (12) |
C18—C13—B1 | 121.50 (11) | N3—C42—C43 | 117.21 (11) |
C15—C14—C13 | 122.65 (12) | C41—C42—C43 | 120.07 (12) |
C15—C14—H14 | 118.7 | N4—C43—C42 | 121.34 (12) |
C13—C14—H14 | 118.7 | N4—C43—H43 | 119.3 |
C16—C15—C14 | 120.31 (13) | C42—C43—H43 | 119.3 |
C16—C15—H15 | 119.8 | C50A—C44—N4 | 124.7 (4) |
C14—C15—H15 | 119.8 | C50A—C44—C45 | 123.1 (4) |
C15—C16—C17 | 118.90 (13) | N4—C44—C45 | 108.20 (11) |
C15—C16—H16 | 120.5 | C50A—C44—C50 | 35.3 (4) |
C17—C16—H16 | 120.5 | N4—C44—C50 | 106.86 (12) |
C16—C17—C18 | 120.05 (13) | C45—C44—C50 | 114.51 (12) |
C16—C17—H17 | 120.0 | C50A—C44—H44A | 74.2 |
C18—C17—H17 | 120.0 | N4—C44—H44A | 109.1 |
C17—C18—C13 | 122.88 (13) | C45—C44—H44A | 109.1 |
C17—C18—H18 | 118.6 | C50—C44—H44A | 109.1 |
C13—C18—H18 | 118.6 | C50A—C44—H44B | 96.6 |
C24—C19—C20 | 114.93 (12) | N4—C44—H44B | 96.6 |
C24—C19—B1 | 124.76 (11) | C45—C44—H44B | 96.6 |
C20—C19—B1 | 120.31 (11) | C50—C44—H44B | 131.4 |
C21—C20—C19 | 123.25 (12) | H44A—C44—H44B | 22.5 |
C21—C20—H20 | 118.4 | C46—C45—C44 | 114.26 (12) |
C19—C20—H20 | 118.4 | C46—C45—H54A | 108.7 |
C20—C21—C22 | 119.85 (13) | C44—C45—H54A | 108.7 |
C20—C21—H21 | 120.1 | C46—C45—H54B | 108.7 |
C22—C21—H21 | 120.1 | C44—C45—H54B | 108.7 |
C23—C22—C21 | 118.86 (12) | H54A—C45—H54B | 107.6 |
C23—C22—H22 | 120.6 | C46—C45—H54C | 108.7 |
C21—C22—H22 | 120.6 | C44—C45—H54C | 108.7 |
C22—C23—C24 | 120.40 (12) | H54A—C45—H54C | 0.0 |
C22—C23—H23 | 119.8 | H54B—C45—H54C | 107.6 |
C24—C23—H23 | 119.8 | C46—C45—H54D | 108.7 |
C23—C24—C19 | 122.70 (12) | C44—C45—H54D | 108.7 |
C23—C24—H24 | 118.7 | H54A—C45—H54D | 107.6 |
C19—C24—H24 | 118.7 | H54B—C45—H54D | 0.0 |
N2—Ag1—N3 | 148.72 (5) | H54C—C45—H54D | 107.6 |
N2—Ag1—N4 | 137.23 (5) | C45—C46—C47 | 113.53 (14) |
N3—Ag1—N4 | 73.05 (4) | C45—C46—H46A | 108.9 |
N2—Ag1—N1 | 72.93 (4) | C47—C46—H46A | 108.9 |
N3—Ag1—N1 | 111.61 (4) | C45—C46—H46B | 108.9 |
N4—Ag1—N1 | 105.16 (4) | C47—C46—H46B | 108.9 |
N4—Ag1A—N2 | 152.8 (2) | H46A—C46—H46B | 107.7 |
N4—Ag1A—N1 | 116.27 (16) | C48A—C47—C46 | 123.7 (6) |
N2—Ag1A—N1 | 71.57 (9) | C48A—C47—C48 | 19.9 (6) |
N4—Ag1A—N3 | 74.82 (10) | C46—C47—C48 | 116.40 (14) |
N2—Ag1A—N3 | 129.94 (19) | C48A—C47—H47A | 88.4 |
N1—Ag1A—N3 | 106.54 (14) | C46—C47—H47A | 108.2 |
C25—N1—C29 | 117.62 (12) | C48—C47—H47A | 108.2 |
C25—N1—Ag1A | 130.14 (12) | C48A—C47—H47B | 117.5 |
C29—N1—Ag1A | 111.44 (11) | C46—C47—H47B | 108.2 |
C25—N1—Ag1 | 133.29 (10) | C48—C47—H47B | 108.2 |
C29—N1—Ag1 | 109.08 (8) | H47A—C47—H47B | 107.3 |
Ag1A—N1—Ag1 | 9.44 (9) | C48A—C47—H47C | 106.9 |
C30—N2—C31 | 117.15 (11) | C46—C47—H47C | 106.5 |
C30—N2—Ag1 | 117.79 (9) | C48—C47—H47C | 93.6 |
C31—N2—Ag1 | 124.98 (8) | H47A—C47—H47C | 124.0 |
C30—N2—Ag1A | 115.85 (12) | H47B—C47—H47C | 18.5 |
C31—N2—Ag1A | 125.32 (11) | C48A—C47—H47D | 105.5 |
Ag1—N2—Ag1A | 9.92 (9) | C46—C47—H47D | 106.7 |
C38—N3—C42 | 117.76 (11) | C48—C47—H47D | 124.4 |
C38—N3—Ag1 | 127.51 (9) | H47A—C47—H47D | 20.8 |
C42—N3—Ag1 | 114.56 (9) | H47B—C47—H47D | 88.7 |
C38—N3—Ag1A | 136.31 (13) | H47C—C47—H47D | 106.5 |
C42—N3—Ag1A | 105.70 (12) | C49—C48—C47 | 118.32 (16) |
Ag1—N3—Ag1A | 8.87 (9) | C49—C48—H48A | 107.7 |
C43—N4—C44 | 119.47 (12) | C47—C48—H48A | 107.7 |
C43—N4—Ag1A | 119.45 (14) | C49—C48—H48B | 107.7 |
C44—N4—Ag1A | 120.19 (14) | C47—C48—H48B | 107.7 |
C43—N4—Ag1 | 112.89 (9) | H48A—C48—H48B | 107.1 |
C44—N4—Ag1 | 127.14 (9) | C48—C49—C50 | 117.99 (16) |
Ag1A—N4—Ag1 | 7.17 (11) | C48—C49—H49A | 107.8 |
N1—C25—C26 | 123.44 (13) | C50—C49—H49A | 107.8 |
N1—C25—H25 | 118.3 | C48—C49—H49B | 107.8 |
C26—C25—H25 | 118.3 | C50—C49—H49B | 107.8 |
C27—C26—C25 | 118.38 (12) | H49A—C49—H49B | 107.1 |
C27—C26—H26 | 120.8 | C49—C50—C44 | 113.38 (13) |
C25—C26—H26 | 120.8 | C49—C50—H50A | 108.9 |
C26—C27—C28 | 119.16 (12) | C44—C50—H50A | 108.9 |
C26—C27—H27 | 120.4 | C49—C50—H50B | 108.9 |
C28—C27—H27 | 120.4 | C44—C50—H50B | 108.9 |
C27—C28—C29 | 118.46 (12) | H50A—C50—H50B | 107.7 |
C27—C28—H28 | 120.8 | C44—C50A—C49A | 106.1 (7) |
C29—C28—H28 | 120.8 | C44—C50A—H50C | 110.5 |
N1—C29—C28 | 122.91 (12) | C49A—C50A—H50C | 110.5 |
N1—C29—C30 | 117.64 (11) | C44—C50A—H50D | 110.5 |
C28—C29—C30 | 119.44 (12) | C49A—C50A—H50D | 110.5 |
N2—C30—C29 | 122.45 (12) | H50C—C50A—H50D | 108.7 |
N2—C30—H30 | 118.8 | C48A—C49A—C50A | 123.0 (10) |
C29—C30—H30 | 118.8 | C48A—C49A—H49C | 106.6 |
N2—C31—C37 | 106.57 (11) | C50A—C49A—H49C | 106.6 |
N2—C31—C32 | 109.93 (11) | C48A—C49A—H49D | 106.6 |
C37—C31—C32 | 115.82 (11) | C50A—C49A—H49D | 106.6 |
N2—C31—H31 | 108.1 | H49C—C49A—H49D | 106.6 |
C37—C31—H31 | 108.1 | C47—C48A—C49A | 116.1 (9) |
C32—C31—H31 | 108.1 | C47—C48A—H48C | 108.3 |
C31—C32—C33 | 116.64 (11) | C49A—C48A—H48C | 108.3 |
C31—C32—H32A | 108.1 | C47—C48A—H48D | 108.3 |
C33—C32—H32A | 108.1 | C49A—C48A—H48D | 108.3 |
C31—C32—H32B | 108.1 | H48C—C48A—H48D | 107.4 |
C33—C32—H32B | 108.1 | ||
C13—B1—C1—C2 | −10.75 (16) | N2—Ag1A—N3—C42 | 176.26 (16) |
C19—B1—C1—C2 | 107.76 (13) | N1—Ag1A—N3—C42 | −104.20 (15) |
C7—B1—C1—C2 | −131.28 (12) | N4—Ag1A—N3—Ag1 | −168.6 (6) |
C13—B1—C1—C6 | 172.15 (11) | N2—Ag1A—N3—Ag1 | −1.6 (4) |
C19—B1—C1—C6 | −69.35 (14) | N1—Ag1A—N3—Ag1 | 77.9 (5) |
C7—B1—C1—C6 | 51.61 (15) | N2—Ag1A—N4—C43 | −168.7 (3) |
C6—C1—C2—C3 | 0.23 (18) | N1—Ag1A—N4—C43 | 90.4 (2) |
B1—C1—C2—C3 | −177.05 (12) | N3—Ag1A—N4—C43 | −10.82 (14) |
C1—C2—C3—C4 | 0.3 (2) | N2—Ag1A—N4—C44 | 22.2 (4) |
C2—C3—C4—C5 | −0.37 (19) | N1—Ag1A—N4—C44 | −78.70 (19) |
C3—C4—C5—C6 | 0.00 (19) | N3—Ag1A—N4—C44 | −179.94 (10) |
C4—C5—C6—C1 | 0.52 (19) | N2—Ag1A—N4—Ag1 | −144.2 (11) |
C2—C1—C6—C5 | −0.61 (18) | N1—Ag1A—N4—Ag1 | 115.0 (9) |
B1—C1—C6—C5 | 176.73 (11) | N3—Ag1A—N4—Ag1 | 13.7 (8) |
C1—B1—C7—C8 | 7.04 (17) | N2—Ag1—N4—C43 | −178.67 (9) |
C13—B1—C7—C8 | −114.34 (13) | N3—Ag1—N4—C43 | −8.19 (9) |
C19—B1—C7—C8 | 127.93 (13) | N1—Ag1—N4—C43 | 100.25 (10) |
C1—B1—C7—C12 | −175.64 (11) | N2—Ag1—N4—C44 | 9.61 (14) |
C13—B1—C7—C12 | 62.98 (14) | N3—Ag1—N4—C44 | −179.92 (11) |
C19—B1—C7—C12 | −54.75 (14) | N1—Ag1—N4—C44 | −71.48 (11) |
C12—C7—C8—C9 | 1.03 (18) | N2—Ag1—N4—Ag1A | 24.4 (8) |
B1—C7—C8—C9 | 178.47 (12) | N3—Ag1—N4—Ag1A | −165.1 (8) |
C7—C8—C9—C10 | −0.5 (2) | N1—Ag1—N4—Ag1A | −56.6 (8) |
C8—C9—C10—C11 | −0.4 (2) | C29—N1—C25—C26 | 0.1 (2) |
C9—C10—C11—C12 | 0.6 (2) | Ag1A—N1—C25—C26 | 168.83 (17) |
C10—C11—C12—C7 | 0.0 (2) | Ag1—N1—C25—C26 | −179.24 (10) |
C8—C7—C12—C11 | −0.77 (19) | N1—C25—C26—C27 | 0.9 (2) |
B1—C7—C12—C11 | −178.37 (12) | C25—C26—C27—C28 | −0.8 (2) |
C1—B1—C13—C14 | −103.12 (13) | C26—C27—C28—C29 | −0.1 (2) |
C19—B1—C13—C14 | 137.73 (12) | C25—N1—C29—C28 | −1.1 (2) |
C7—B1—C13—C14 | 19.25 (16) | Ag1A—N1—C29—C28 | −171.90 (15) |
C1—B1—C13—C18 | 75.83 (14) | Ag1—N1—C29—C28 | 178.35 (11) |
C19—B1—C13—C18 | −43.33 (15) | C25—N1—C29—C30 | 177.69 (12) |
C7—B1—C13—C18 | −161.80 (11) | Ag1A—N1—C29—C30 | 6.92 (18) |
C18—C13—C14—C15 | −0.65 (19) | Ag1—N1—C29—C30 | −2.82 (14) |
B1—C13—C14—C15 | 178.36 (12) | C27—C28—C29—N1 | 1.2 (2) |
C13—C14—C15—C16 | 0.9 (2) | C27—C28—C29—C30 | −177.64 (12) |
C14—C15—C16—C17 | −0.5 (2) | C31—N2—C30—C29 | −174.87 (12) |
C15—C16—C17—C18 | −0.1 (2) | Ag1—N2—C30—C29 | 2.10 (17) |
C16—C17—C18—C13 | 0.4 (2) | Ag1A—N2—C30—C29 | −8.8 (2) |
C14—C13—C18—C17 | 0.00 (19) | N1—C29—C30—N2 | 0.8 (2) |
B1—C13—C18—C17 | −179.03 (12) | C28—C29—C30—N2 | 179.70 (13) |
C1—B1—C19—C24 | 20.96 (16) | C30—N2—C31—C37 | 92.35 (14) |
C13—B1—C19—C24 | 140.62 (12) | Ag1—N2—C31—C37 | −84.38 (12) |
C7—B1—C19—C24 | −101.40 (14) | Ag1A—N2—C31—C37 | −72.25 (18) |
C1—B1—C19—C20 | −159.69 (11) | C30—N2—C31—C32 | −141.41 (12) |
C13—B1—C19—C20 | −40.03 (15) | Ag1—N2—C31—C32 | 41.87 (14) |
C7—B1—C19—C20 | 77.95 (14) | Ag1A—N2—C31—C32 | 54.00 (19) |
C24—C19—C20—C21 | 1.25 (19) | N2—C31—C32—C33 | −87.85 (14) |
B1—C19—C20—C21 | −178.16 (12) | C37—C31—C32—C33 | 32.98 (17) |
C19—C20—C21—C22 | −1.7 (2) | C31—C32—C33—C34 | −84.03 (15) |
C20—C21—C22—C23 | 0.8 (2) | C32—C33—C34—C35 | 72.20 (16) |
C21—C22—C23—C24 | 0.4 (2) | C33—C34—C35—C36 | −54.07 (18) |
C22—C23—C24—C19 | −0.8 (2) | C34—C35—C36—C37 | 69.82 (16) |
C20—C19—C24—C23 | −0.01 (19) | N2—C31—C37—C36 | 167.12 (11) |
B1—C19—C24—C23 | 179.37 (12) | C32—C31—C37—C36 | 44.50 (17) |
N4—Ag1A—N1—C25 | −25.6 (3) | C35—C36—C37—C31 | −88.65 (15) |
N2—Ag1A—N1—C25 | −177.30 (14) | C42—N3—C38—C39 | 0.16 (19) |
N3—Ag1A—N1—C25 | 55.3 (2) | Ag1—N3—C38—C39 | −174.86 (10) |
N4—Ag1A—N1—C29 | 143.70 (16) | Ag1A—N3—C38—C39 | −173.28 (14) |
N2—Ag1A—N1—C29 | −8.02 (15) | N3—C38—C39—C40 | 0.9 (2) |
N3—Ag1A—N1—C29 | −135.39 (13) | C38—C39—C40—C41 | −0.9 (2) |
N4—Ag1A—N1—Ag1 | −139.0 (6) | C39—C40—C41—C42 | −0.08 (19) |
N2—Ag1A—N1—Ag1 | 69.3 (5) | C38—N3—C42—C41 | −1.19 (18) |
N3—Ag1A—N1—Ag1 | −58.1 (5) | Ag1—N3—C42—C41 | 174.47 (10) |
N2—Ag1—N1—C25 | −177.82 (15) | Ag1A—N3—C42—C41 | 174.10 (13) |
N3—Ag1—N1—C25 | 35.04 (15) | C38—N3—C42—C43 | 177.52 (11) |
N4—Ag1—N1—C25 | −42.39 (14) | Ag1—N3—C42—C43 | −6.81 (14) |
N2—Ag1—N1—C29 | 2.80 (9) | Ag1A—N3—C42—C43 | −7.18 (15) |
N3—Ag1—N1—C29 | −144.33 (9) | C40—C41—C42—N3 | 1.2 (2) |
N4—Ag1—N1—C29 | 138.23 (9) | C40—C41—C42—C43 | −177.52 (12) |
N2—Ag1—N1—Ag1A | −103.3 (5) | C44—N4—C43—C42 | −179.68 (11) |
N3—Ag1—N1—Ag1A | 109.6 (5) | Ag1A—N4—C43—C42 | 11.1 (2) |
N4—Ag1—N1—Ag1A | 32.1 (5) | Ag1—N4—C43—C42 | 7.90 (16) |
N3—Ag1—N2—C30 | 101.11 (13) | N3—C42—C43—N4 | −0.98 (18) |
N4—Ag1—N2—C30 | −96.63 (11) | C41—C42—C43—N4 | 177.77 (12) |
N1—Ag1—N2—C30 | −2.57 (10) | C43—N4—C44—C50A | −108.7 (5) |
N3—Ag1—N2—C31 | −82.18 (13) | Ag1A—N4—C44—C50A | 60.4 (5) |
N4—Ag1—N2—C31 | 80.08 (12) | Ag1—N4—C44—C50A | 62.5 (5) |
N1—Ag1—N2—C31 | 174.14 (11) | C43—N4—C44—C45 | 93.33 (15) |
N3—Ag1—N2—Ag1A | −177.6 (6) | Ag1A—N4—C44—C45 | −97.55 (16) |
N4—Ag1—N2—Ag1A | −15.4 (5) | Ag1—N4—C44—C45 | −95.43 (13) |
N1—Ag1—N2—Ag1A | 78.7 (5) | C43—N4—C44—C50 | −142.90 (13) |
N4—Ag1A—N2—C30 | −103.1 (4) | Ag1A—N4—C44—C50 | 26.22 (17) |
N1—Ag1A—N2—C30 | 8.72 (15) | Ag1—N4—C44—C50 | 28.34 (15) |
N3—Ag1A—N2—C30 | 105.17 (19) | C50A—C44—C45—C46 | 21.7 (5) |
N4—Ag1A—N2—C31 | 61.6 (4) | N4—C44—C45—C46 | −179.86 (13) |
N1—Ag1A—N2—C31 | 173.49 (11) | C50—C44—C45—C46 | 61.11 (17) |
N3—Ag1A—N2—C31 | −90.1 (2) | C44—C45—C46—C47 | −76.13 (17) |
N4—Ag1A—N2—Ag1 | 153.2 (8) | C45—C46—C47—C48A | 61.1 (8) |
N1—Ag1A—N2—Ag1 | −95.0 (5) | C45—C46—C47—C48 | 82.50 (18) |
N3—Ag1A—N2—Ag1 | 1.5 (4) | C48A—C47—C48—C49 | 82.3 (16) |
N2—Ag1—N3—C38 | −9.59 (16) | C46—C47—C48—C49 | −34.4 (2) |
N4—Ag1—N3—C38 | −177.09 (11) | C47—C48—C49—C50 | −38.3 (3) |
N1—Ag1—N3—C38 | 82.93 (11) | C48—C49—C50—C44 | 82.40 (19) |
N2—Ag1—N3—C42 | 175.25 (9) | C50A—C44—C50—C49 | 40.5 (7) |
N4—Ag1—N3—C42 | 7.75 (9) | N4—C44—C50—C49 | 167.58 (13) |
N1—Ag1—N3—C42 | −92.23 (9) | C45—C44—C50—C49 | −72.63 (17) |
N2—Ag1—N3—Ag1A | 177.5 (6) | N4—C44—C50A—C49A | −102.4 (7) |
N4—Ag1—N3—Ag1A | 10.0 (5) | C45—C44—C50A—C49A | 52.4 (9) |
N1—Ag1—N3—Ag1A | −90.0 (6) | C50—C44—C50A—C49A | −34.0 (5) |
N4—Ag1A—N3—C38 | −176.78 (13) | C44—C50A—C49A—C48A | −87.5 (12) |
N2—Ag1A—N3—C38 | −9.8 (3) | C46—C47—C48A—C49A | −31.6 (15) |
N1—Ag1A—N3—C38 | 69.8 (2) | C48—C47—C48A—C49A | −106 (2) |
N4—Ag1A—N3—C42 | 9.25 (12) | C50A—C49A—C48A—C47 | 54.7 (17) |
Experimental details
Crystal data | |
Chemical formula | [Ag(C26H36N4)2]C24H20B |
Mr | 831.67 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.2093 (3), 15.2132 (2), 21.6851 (6) |
β (°) | 105.462 (2) |
V (Å3) | 4200.03 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.50 × 0.38 × 0.24 |
Data collection | |
Diffractometer | Stoe IPDS II |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.781, 0.886 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32871, 11472, 10372 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.691 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.079, 1.08 |
No. of reflections | 11472 |
No. of parameters | 524 |
No. of restraints | 8 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.58 |
Computer programs: X-AREA (Stoe & Cie, 2006), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).
Ag1—N2 | 2.2025 (12) | Ag1A—N4 | 2.045 (4) |
Ag1—N3 | 2.2757 (12) | Ag1A—N2 | 2.310 (3) |
Ag1—N4 | 2.3426 (13) | Ag1A—N1 | 2.444 (3) |
Ag1—N1 | 2.4646 (12) | Ag1A—N3 | 2.449 (4) |
N2—Ag1—N3 | 148.72 (5) | N4—Ag1A—N2 | 152.8 (2) |
N2—Ag1—N4 | 137.23 (5) | N4—Ag1A—N1 | 116.27 (16) |
N3—Ag1—N4 | 73.05 (4) | N2—Ag1A—N1 | 71.57 (9) |
N2—Ag1—N1 | 72.93 (4) | N4—Ag1A—N3 | 74.82 (10) |
N3—Ag1—N1 | 111.61 (4) | N2—Ag1A—N3 | 129.94 (19) |
N4—Ag1—N1 | 105.16 (4) | N1—Ag1A—N3 | 106.54 (14) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Pyridinecarbaldehyde and its substituted derivatives condense with amines to furnish a range of diimine compounds; such compounds have been used as ligands of transition metals. Among such complexes whose structures have been described are, for example, compounds of copper(I) (Dehghanpour et al., 2007), silver(I) (Bowyer et al., 1998; Hannon et al., 1999) and Ru(II) (Chakraborty et al., 1999). The title complex, (I), was prepared by the reaction of AgBPh4 with the bidentate ligand N,N'-cycloheptyl-pyridin-2-ylmethylene-amine.
One of the cycloheptyl substituents proved to show disorder with an alternative conformation (shown bright transparent in figure 1a) occupied at 12.7 (2)%, which will be discussed in detail in the next paragraph. The general geometry for the complex is similar with either of the two alternative orientations. While a tetrahedral geometry might be expected for four coordinated silver(I), the coordination sphere around the metal ion in this complex is strongly distorted by the restricting bite angles of the chelating ligand. The intraligand N1–Ag1–N2 and N3–Ag1–N4 angles [72.93 (4), 73.05 (4) °] are much less than 109.5 °. On the contrary the N2–Ag1–N3 and N2–Ag1–N4 angles [148.72 (5), 137.23 (5) °] are much larger than those of a tetrahedral complex. Ag1 is only 0.1135 (5) Å above the plane of N2, N3, and N4, and the bond Ag1—N1 is inclined by 69.72 (3)° with respect to this plane. The Ag–N bond lengths are similar to the corresponding bond distances in related complexes (Amirnasr et al., 2006; Bowyer et al., 1998; Hannon et al., 1999). The dihedral angle between the two chelate rings is 87.06 (4) °. The environments of the imine and pyridine nitrogen atoms are planar with the sums of the three N atom bond angles being 360.0 ° and 359.9 ° for N1 and N2, respectively. Despite the fact that the nitrogen atom (N1) is sp2 hybridized, some strain in the chelate ring is suggested by the deviation from the 120 ° angle at nitrogen (C25–N1–C29 = 117.6 (1)°).
In the arrangement with the at N4 disordered cycloheptyl rest (bright transparent in figure 1a) the C50 methylene group is more remote of Ag1, the silver atom also moves out by 0.405 (5) Å toward an alternative position. Here the most obtuse angle changes from N2—Ag1—N3 (148.72 (4)°) to N2—Ag1a—N4 (152.8 (2)°), and Ag1 approaches N4. In both alternative conformations, the shortest Ag···H contacts are similar (Ag1···H33a 2.85 Å, Ag1···H50a 3.14 Å; Ag1a···H33a 2.90 Å, Ag1a···H49c 3.11 Å) and are close to the sum of the Van der Waals radii (2.92 Å). Apparently the coordinational compromise provoked by the geometrical restrictions of the chelate ligands may find different solutions with similar energy.