supplementary materials


Acta Cryst. (2007). E63, m1872    [ doi:10.1107/S1600536807027079 ]

Bis[2-(cycloheptyliminomethyl)pyridine-[kappa]2N,N']silver(I) tetraphenylborate

W. Massa, S. Dehghanpour, G. Tashakori and K. Aoki

Abstract top

In the title complex, [Ag(C26H36N4)2](C24H20B), the AgI atom has a distorted tetrahedral coordination. The organic ligand is bidentate, coordinating the AgI atom via two imine N atoms. One of the cycloheptyl groups and the Ag atom are disordered over two sites, with occupancy factors of ca 0.87 and 0.13. In this arrangement, the closest methylene group is more remote and the Ag atom also moves out by 0.405 (5) Å toward an alternative position.

Comment top

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.

Related literature top

For related literature, see: Amirnasr et al. (2006); Bowyer et al. (1998); Chakraborty et al. (1999); Dehghanpour (2007); Hannon et al. (1999).

Experimental top

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%.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Structures of a) the cation [Ag(C26H38N4)2]+, b) the anion (C24H20B) in the crystal. Thermal ellipsoids are drawn at the 50% probability level, and hydrogen atoms are shown as spheres of arbitrary radius. Less occupied alternative positions in the disordered cation are drawn bright transparent.
Bis[2-(cycloheptyliminomethyl)pyridine-k2N,N']silver(I) tetraphenylborate top
Crystal data top
[Ag(C26H36N4)2]C24H20BF000 = 1744
Mr = 831.67Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 49514 reflections
a = 13.2093 (3) Åθ = 1.6–29.8º
b = 15.2132 (2) ŵ = 0.52 mm1
c = 21.6851 (6) ÅT = 100 (2) K
β = 105.462 (2)ºPrism, light-yellow
V = 4200.03 (16) Å30.50 × 0.38 × 0.24 mm
Z = 4
Data collection top
Stoe IPDS II
diffractometer
11472 independent reflections
Radiation source: fine-focus sealed tube10372 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
Detector resolution: 6.7 pixels mm-1θmax = 29.4º
T = 100(2) Kθmin = 1.6º
ω scansh = 18→18
Absorption correction: multi-scan
(Blessing, 1995)
k = 21→20
Tmin = 0.781, Tmax = 0.886l = 28→29
32871 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.079  w = 1/[σ2(Fo2) + (0.0419P)2 + 1.6408P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
11472 reflectionsΔρmax = 0.53 e Å3
524 parametersΔρmin = 0.58 e Å3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag(C26H36N4)2]C24H20BV = 4200.03 (16) Å3
Mr = 831.67Z = 4
Monoclinic, P21/cMo Kα
a = 13.2093 (3) ŵ = 0.52 mm1
b = 15.2132 (2) ÅT = 100 (2) K
c = 21.6851 (6) Å0.50 × 0.38 × 0.24 mm
β = 105.462 (2)º
Data collection top
Stoe IPDS II
diffractometer
11472 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
10372 reflections with I > 2σ(I)
Tmin = 0.781, Tmax = 0.886Rint = 0.017
32871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0308 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.08Δρmax = 0.53 e Å3
11472 reflectionsΔρmin = 0.58 e Å3
524 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
B10.71523 (11)0.77457 (9)0.04699 (7)0.0190 (2)
C10.65428 (9)0.77615 (8)0.10404 (6)0.0193 (2)
C20.61436 (10)0.70078 (8)0.12635 (6)0.0212 (2)
H20.62560.64530.10910.025*
C30.55857 (10)0.70357 (9)0.17289 (6)0.0226 (2)
H30.53320.65060.18670.027*
C40.54016 (10)0.78309 (9)0.19895 (6)0.0224 (2)
H40.50200.78540.23040.027*
C50.57857 (9)0.85956 (9)0.17828 (6)0.0213 (2)
H50.56670.91470.19560.026*
C60.63446 (9)0.85551 (8)0.13219 (6)0.0205 (2)
H60.66040.90870.11920.025*
C70.82698 (10)0.83014 (8)0.06767 (6)0.0201 (2)
C80.87241 (10)0.86601 (9)0.12822 (6)0.0222 (2)
H80.83640.85970.16050.027*
C90.96835 (10)0.91059 (9)0.14326 (7)0.0259 (3)
H90.99580.93420.18490.031*
C101.02359 (10)0.92053 (9)0.09771 (7)0.0284 (3)
H101.08860.95110.10760.034*
C110.98216 (11)0.88498 (10)0.03731 (7)0.0280 (3)
H111.01930.89060.00560.034*
C120.88647 (10)0.84116 (9)0.02314 (7)0.0241 (2)
H120.85990.81750.01860.029*
C130.74120 (10)0.67239 (8)0.03106 (6)0.0202 (2)
C140.84116 (10)0.63461 (9)0.05230 (6)0.0224 (2)
H140.89740.66980.07620.027*
C150.86144 (11)0.54728 (9)0.03978 (7)0.0272 (3)
H150.93030.52410.05560.033*
C160.78187 (12)0.49443 (9)0.00444 (7)0.0284 (3)
H160.79550.43510.00440.034*
C170.68159 (12)0.52949 (9)0.01789 (7)0.0276 (3)
H170.62600.49410.04230.033*
C180.66253 (10)0.61634 (9)0.00446 (7)0.0245 (2)
H180.59330.63880.02000.029*
C190.63786 (10)0.81801 (8)0.01880 (6)0.0201 (2)
C200.65518 (11)0.80003 (9)0.07887 (6)0.0236 (2)
H200.71070.76120.08060.028*
C210.59516 (11)0.83618 (9)0.13563 (6)0.0264 (3)
H210.61110.82320.17490.032*
C220.51163 (11)0.89140 (9)0.13496 (7)0.0268 (3)
H220.46950.91600.17360.032*
C230.49090 (10)0.90999 (9)0.07703 (7)0.0268 (3)
H230.43380.94730.07590.032*
C240.55340 (10)0.87427 (9)0.02035 (6)0.0231 (2)
H240.53800.88870.01880.028*
Ag10.85288 (4)0.19026 (4)0.14911 (2)0.02404 (7)0.873 (2)
Ag1A0.8437 (2)0.2153 (3)0.15095 (15)0.0248 (5)0.127 (2)
N11.01864 (9)0.26352 (8)0.14765 (5)0.0261 (2)
N20.96308 (9)0.17026 (8)0.24404 (5)0.0224 (2)
N30.76931 (8)0.13463 (7)0.05138 (5)0.0215 (2)
N40.72043 (9)0.29027 (8)0.10113 (6)0.0240 (2)
C251.04846 (11)0.31078 (10)0.10380 (7)0.0276 (3)
H250.99860.32110.06390.033*
C261.14861 (11)0.34568 (9)0.11333 (7)0.0254 (3)
H261.16640.37970.08100.031*
C271.22166 (10)0.32969 (9)0.17092 (7)0.0243 (2)
H271.29110.35200.17870.029*
C281.19238 (10)0.28065 (9)0.21724 (6)0.0225 (2)
H281.24120.26860.25720.027*
C291.08999 (10)0.24949 (9)0.20387 (6)0.0220 (2)
C301.05590 (10)0.20018 (8)0.25325 (6)0.0223 (2)
H301.10500.19030.29350.027*
C310.93615 (10)0.12872 (9)0.29904 (6)0.0224 (2)
H311.00280.10820.32960.027*
C320.86636 (10)0.04840 (9)0.27667 (7)0.0261 (3)
H32A0.87990.00550.31230.031*
H32B0.88830.02060.24100.031*
C330.74781 (11)0.06488 (10)0.25437 (7)0.0282 (3)
H33A0.73510.12150.23100.034*
H33B0.71480.01790.22410.034*
C340.69492 (11)0.06756 (10)0.30913 (7)0.0283 (3)
H34A0.61800.06320.29050.034*
H34B0.71730.01490.33620.034*
C350.71723 (11)0.14850 (10)0.35198 (7)0.0277 (3)
H35A0.68320.14050.38710.033*
H35B0.68400.20000.32660.033*
C360.83336 (11)0.16900 (10)0.38129 (7)0.0274 (3)
H36A0.86900.11540.40240.033*
H36B0.83960.21480.41460.033*
C370.88903 (11)0.20085 (9)0.33188 (7)0.0254 (3)
H37A0.83810.23470.29860.031*
H37B0.94600.24160.35330.031*
C380.78747 (10)0.05777 (9)0.02625 (6)0.0241 (2)
H380.83690.01850.05220.029*
C390.73743 (11)0.03279 (9)0.03600 (7)0.0258 (3)
H390.75160.02270.05200.031*
C400.66676 (11)0.08999 (9)0.07412 (6)0.0257 (3)
H400.63210.07490.11710.031*
C410.64692 (10)0.16987 (9)0.04885 (6)0.0235 (2)
H410.59860.21040.07420.028*
C420.69887 (10)0.18943 (8)0.01403 (6)0.0206 (2)
C430.67639 (10)0.27201 (9)0.04304 (6)0.0231 (2)
H430.62790.31250.01780.028*
C440.69530 (11)0.37288 (9)0.12804 (7)0.0270 (3)
H44A0.67080.41650.09270.032*0.873 (2)
H44B0.65030.39770.08720.032*0.127 (2)
C450.60658 (11)0.35548 (9)0.15949 (7)0.0278 (3)
H54A0.54550.33160.12680.033*0.873 (2)
H54B0.63000.31000.19290.033*0.873 (2)
H54C0.54550.33160.12680.033*0.127 (2)
H54D0.63000.31000.19290.033*0.127 (2)
C460.57134 (13)0.43643 (10)0.18983 (8)0.0349 (3)
H46A0.50140.42470.19670.042*
H46B0.56390.48640.15970.042*
C470.64702 (17)0.46260 (11)0.25355 (8)0.0444 (4)
H47A0.67290.40820.27770.053*0.873 (2)
H47B0.60710.49600.27850.053*0.873 (2)
H47C0.61330.51170.27060.053*0.127 (2)
H47D0.64990.41240.28300.053*0.127 (2)
C480.74320 (17)0.51826 (15)0.24986 (9)0.0389 (4)0.873 (2)
H48A0.72220.58090.24800.047*0.873 (2)
H48B0.79850.50980.29040.047*0.873 (2)
C490.79177 (14)0.50138 (11)0.19561 (10)0.0345 (4)0.873 (2)
H49A0.86390.52580.20790.041*0.873 (2)
H49B0.75140.53520.15810.041*0.873 (2)
C500.79858 (12)0.40667 (10)0.17443 (8)0.0262 (3)0.873 (2)
H50A0.81670.36840.21270.031*0.873 (2)
H50B0.85600.40190.15310.031*0.873 (2)
C50A0.7656 (8)0.4468 (6)0.1444 (5)0.0262 (3)0.127 (2)
H50C0.72730.50250.13080.031*0.127 (2)
H50D0.82310.44190.12320.031*0.127 (2)
C49A0.8086 (9)0.4445 (8)0.2158 (5)0.0345 (4)0.127 (2)
H49C0.81700.38170.22810.041*0.127 (2)
H49D0.88020.46970.22540.041*0.127 (2)
C48A0.7548 (8)0.4876 (10)0.2607 (7)0.0389 (4)0.127 (2)
H48C0.79540.47430.30500.047*0.127 (2)
H48D0.75730.55200.25490.047*0.127 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0198 (6)0.0187 (6)0.0186 (6)0.0007 (5)0.0055 (5)0.0005 (5)
C10.0166 (5)0.0217 (5)0.0184 (5)0.0013 (4)0.0025 (4)0.0011 (4)
C20.0204 (5)0.0212 (5)0.0214 (6)0.0015 (4)0.0046 (4)0.0008 (4)
C30.0202 (5)0.0246 (6)0.0231 (6)0.0009 (4)0.0058 (5)0.0034 (5)
C40.0176 (5)0.0297 (6)0.0195 (5)0.0015 (4)0.0046 (4)0.0013 (5)
C50.0183 (5)0.0242 (6)0.0202 (5)0.0020 (4)0.0032 (4)0.0016 (4)
C60.0184 (5)0.0217 (5)0.0207 (5)0.0004 (4)0.0040 (4)0.0006 (4)
C70.0201 (5)0.0180 (5)0.0224 (6)0.0023 (4)0.0060 (4)0.0016 (4)
C80.0203 (5)0.0229 (6)0.0231 (6)0.0019 (4)0.0053 (4)0.0007 (5)
C90.0210 (6)0.0269 (6)0.0274 (6)0.0003 (5)0.0024 (5)0.0033 (5)
C100.0201 (6)0.0268 (6)0.0377 (7)0.0023 (5)0.0068 (5)0.0007 (6)
C110.0241 (6)0.0298 (6)0.0334 (7)0.0009 (5)0.0132 (5)0.0001 (5)
C120.0237 (6)0.0246 (6)0.0250 (6)0.0003 (5)0.0085 (5)0.0007 (5)
C130.0222 (6)0.0212 (5)0.0178 (5)0.0007 (4)0.0064 (4)0.0015 (4)
C140.0236 (6)0.0227 (6)0.0198 (5)0.0025 (4)0.0036 (4)0.0009 (4)
C150.0299 (6)0.0249 (6)0.0266 (6)0.0077 (5)0.0071 (5)0.0031 (5)
C160.0396 (7)0.0197 (6)0.0282 (7)0.0025 (5)0.0132 (6)0.0001 (5)
C170.0330 (7)0.0234 (6)0.0266 (6)0.0046 (5)0.0084 (5)0.0026 (5)
C180.0243 (6)0.0236 (6)0.0253 (6)0.0008 (5)0.0060 (5)0.0003 (5)
C190.0201 (5)0.0201 (5)0.0199 (5)0.0012 (4)0.0049 (4)0.0016 (4)
C200.0247 (6)0.0248 (6)0.0211 (6)0.0022 (5)0.0056 (5)0.0000 (5)
C210.0303 (6)0.0277 (6)0.0199 (6)0.0018 (5)0.0046 (5)0.0007 (5)
C220.0249 (6)0.0280 (6)0.0240 (6)0.0019 (5)0.0004 (5)0.0063 (5)
C230.0203 (6)0.0283 (6)0.0310 (7)0.0032 (5)0.0053 (5)0.0061 (5)
C240.0216 (5)0.0246 (6)0.0237 (6)0.0013 (4)0.0072 (5)0.0026 (5)
Ag10.02016 (9)0.02887 (17)0.01943 (8)0.00104 (10)0.00109 (6)0.00182 (11)
Ag1A0.0202 (6)0.0317 (12)0.0183 (5)0.0034 (8)0.0019 (4)0.0030 (8)
N10.0232 (5)0.0343 (6)0.0197 (5)0.0017 (4)0.0038 (4)0.0028 (4)
N20.0209 (5)0.0265 (5)0.0192 (5)0.0027 (4)0.0041 (4)0.0012 (4)
N30.0193 (5)0.0232 (5)0.0207 (5)0.0001 (4)0.0029 (4)0.0021 (4)
N40.0250 (5)0.0243 (5)0.0239 (5)0.0027 (4)0.0085 (4)0.0021 (4)
C250.0273 (6)0.0350 (7)0.0199 (6)0.0002 (5)0.0055 (5)0.0039 (5)
C260.0298 (6)0.0256 (6)0.0235 (6)0.0002 (5)0.0117 (5)0.0011 (5)
C270.0230 (6)0.0249 (6)0.0269 (6)0.0019 (5)0.0100 (5)0.0020 (5)
C280.0197 (5)0.0260 (6)0.0212 (6)0.0008 (4)0.0046 (4)0.0009 (5)
C290.0213 (5)0.0253 (6)0.0194 (5)0.0007 (4)0.0056 (4)0.0001 (5)
C300.0213 (6)0.0263 (6)0.0181 (5)0.0015 (4)0.0030 (4)0.0007 (4)
C310.0189 (5)0.0274 (6)0.0200 (5)0.0028 (4)0.0035 (4)0.0025 (5)
C320.0248 (6)0.0246 (6)0.0306 (7)0.0026 (5)0.0103 (5)0.0020 (5)
C330.0240 (6)0.0316 (7)0.0282 (6)0.0085 (5)0.0056 (5)0.0048 (5)
C340.0217 (6)0.0310 (7)0.0335 (7)0.0041 (5)0.0093 (5)0.0002 (6)
C350.0245 (6)0.0292 (7)0.0314 (7)0.0013 (5)0.0110 (5)0.0022 (5)
C360.0272 (6)0.0324 (7)0.0239 (6)0.0031 (5)0.0091 (5)0.0016 (5)
C370.0256 (6)0.0263 (6)0.0248 (6)0.0056 (5)0.0074 (5)0.0018 (5)
C380.0230 (6)0.0234 (6)0.0255 (6)0.0020 (4)0.0057 (5)0.0036 (5)
C390.0294 (6)0.0218 (6)0.0280 (6)0.0018 (5)0.0107 (5)0.0019 (5)
C400.0257 (6)0.0304 (6)0.0201 (6)0.0035 (5)0.0044 (5)0.0030 (5)
C410.0217 (6)0.0280 (6)0.0189 (6)0.0003 (5)0.0023 (4)0.0015 (5)
C420.0190 (5)0.0219 (5)0.0202 (6)0.0006 (4)0.0043 (4)0.0013 (4)
C430.0230 (6)0.0232 (6)0.0227 (6)0.0012 (4)0.0055 (5)0.0018 (5)
C440.0334 (7)0.0237 (6)0.0270 (6)0.0018 (5)0.0135 (5)0.0016 (5)
C450.0282 (6)0.0254 (6)0.0329 (7)0.0010 (5)0.0134 (5)0.0004 (5)
C460.0377 (8)0.0293 (7)0.0448 (9)0.0043 (6)0.0236 (7)0.0024 (6)
C470.0813 (13)0.0296 (8)0.0296 (8)0.0048 (8)0.0272 (8)0.0001 (6)
C480.0478 (10)0.0364 (11)0.0262 (9)0.0132 (8)0.0009 (7)0.0059 (8)
C490.0322 (8)0.0241 (7)0.0437 (10)0.0002 (6)0.0042 (7)0.0069 (7)
C500.0251 (7)0.0228 (7)0.0297 (8)0.0001 (5)0.0056 (6)0.0034 (6)
C50A0.0251 (7)0.0228 (7)0.0297 (8)0.0001 (5)0.0056 (6)0.0034 (6)
C49A0.0322 (8)0.0241 (7)0.0437 (10)0.0002 (6)0.0042 (7)0.0069 (7)
C48A0.0478 (10)0.0364 (11)0.0262 (9)0.0132 (8)0.0009 (7)0.0059 (8)
Geometric parameters (Å, °) top
B1—C11.6463 (18)C28—C291.3890 (17)
B1—C131.6483 (18)C28—H280.9500
B1—C191.6550 (19)C29—C301.4728 (17)
B1—C71.6558 (19)C30—H300.9500
C1—C21.4009 (17)C31—C371.5281 (19)
C1—C61.4086 (17)C31—C321.5296 (18)
C2—C31.4002 (18)C31—H311.0000
C2—H20.9500C32—C331.5314 (19)
C3—C41.3839 (19)C32—H32A0.9900
C3—H30.9500C32—H32B0.9900
C4—C51.3902 (18)C33—C341.5305 (19)
C4—H40.9500C33—H33A0.9900
C5—C61.3934 (17)C33—H33B0.9900
C5—H50.9500C34—C351.523 (2)
C6—H60.9500C34—H34A0.9900
C7—C81.4006 (18)C34—H34B0.9900
C7—C121.4081 (17)C35—C361.528 (2)
C8—C91.3972 (18)C35—H35A0.9900
C8—H80.9500C35—H35B0.9900
C9—C101.384 (2)C36—C371.5309 (19)
C9—H90.9500C36—H36A0.9900
C10—C111.388 (2)C36—H36B0.9900
C10—H100.9500C37—H37A0.9900
C11—C121.3891 (18)C37—H37B0.9900
C11—H110.9500C38—C391.3885 (19)
C12—H120.9500C38—H380.9500
C13—C141.4006 (17)C39—C401.3786 (19)
C13—C181.4049 (18)C39—H390.9500
C14—C151.3961 (18)C40—C411.3866 (19)
C14—H140.9500C40—H400.9500
C15—C161.382 (2)C41—C421.3854 (18)
C15—H150.9500C41—H410.9500
C16—C171.390 (2)C42—C431.4705 (18)
C16—H160.9500C43—H430.9500
C17—C181.3904 (19)C44—C50A1.441 (7)
C17—H170.9500C44—C451.5279 (18)
C18—H180.9500C44—C501.551 (2)
C19—C241.3995 (17)C44—H44A1.0000
C19—C201.4082 (18)C44—H44B1.0000
C20—C211.3876 (19)C45—C461.526 (2)
C20—H200.9500C45—H54A0.9900
C21—C221.390 (2)C45—H54B0.9900
C21—H210.9500C45—H54C0.9900
C22—C231.384 (2)C45—H54D0.9900
C22—H220.9500C46—C471.527 (3)
C23—C241.3951 (18)C46—H46A0.9900
C23—H230.9500C46—H46B0.9900
C24—H240.9500C47—C48A1.441 (9)
Ag1—N22.2025 (12)C47—C481.547 (3)
Ag1—N32.2757 (12)C47—H47A0.9900
Ag1—N42.3426 (13)C47—H47B0.9900
Ag1—N12.4646 (12)C47—H47C0.9899
Ag1A—N42.045 (4)C47—H47D0.9899
Ag1A—N22.310 (3)C48—C491.505 (3)
Ag1A—N12.444 (3)C48—H48A0.9900
Ag1A—N32.449 (4)C48—H48B0.9900
N1—C251.3327 (18)C49—C501.522 (2)
N1—C291.3444 (17)C49—H49A0.9900
N2—C301.2728 (17)C49—H49B0.9900
N2—C311.4746 (16)C50—H50A0.9900
N3—C381.3386 (17)C50—H50B0.9900
N3—C421.3472 (16)C50A—C49A1.501 (9)
N4—C431.2695 (17)C50A—H50C0.9900
N4—C441.4606 (17)C50A—H50D0.9900
C25—C261.389 (2)C49A—C48A1.500 (9)
C25—H250.9500C49A—H49C0.9900
C26—C271.381 (2)C49A—H49D0.9900
C26—H260.9500C48A—H48C0.9900
C27—C281.3866 (18)C48A—H48D0.9900
C27—H270.9500
C1—B1—C13110.00 (10)H32A—C32—H32B107.3
C1—B1—C19109.19 (10)C34—C33—C32113.54 (12)
C13—B1—C19108.13 (10)C34—C33—H33A108.9
C1—B1—C7111.61 (10)C32—C33—H33A108.9
C13—B1—C7108.54 (10)C34—C33—H33B108.9
C19—B1—C7109.31 (10)C32—C33—H33B108.9
C2—C1—C6114.91 (11)H33A—C33—H33B107.7
C2—C1—B1123.51 (11)C35—C34—C33116.15 (11)
C6—C1—B1121.52 (11)C35—C34—H34A108.2
C3—C2—C1122.90 (12)C33—C34—H34A108.2
C3—C2—H2118.6C35—C34—H34B108.2
C1—C2—H2118.6C33—C34—H34B108.2
C4—C3—C2120.28 (12)H34A—C34—H34B107.4
C4—C3—H3119.9C34—C35—C36115.36 (12)
C2—C3—H3119.9C34—C35—H35A108.4
C3—C4—C5118.75 (12)C36—C35—H35A108.4
C3—C4—H4120.6C34—C35—H35B108.4
C5—C4—H4120.6C36—C35—H35B108.4
C4—C5—C6120.20 (12)H35A—C35—H35B107.5
C4—C5—H5119.9C35—C36—C37112.94 (12)
C6—C5—H5119.9C35—C36—H36A109.0
C5—C6—C1122.96 (12)C37—C36—H36A109.0
C5—C6—H6118.5C35—C36—H36B109.0
C1—C6—H6118.5C37—C36—H36B109.0
C8—C7—C12114.75 (11)H36A—C36—H36B107.8
C8—C7—B1125.52 (11)C31—C37—C36115.48 (11)
C12—C7—B1119.69 (11)C31—C37—H37A108.4
C9—C8—C7122.90 (12)C36—C37—H37A108.4
C9—C8—H8118.5C31—C37—H37B108.4
C7—C8—H8118.5C36—C37—H37B108.4
C10—C9—C8120.30 (13)H37A—C37—H37B107.5
C10—C9—H9119.9N3—C38—C39122.99 (12)
C8—C9—H9119.9N3—C38—H38118.5
C9—C10—C11118.74 (12)C39—C38—H38118.5
C9—C10—H10120.6C40—C39—C38118.75 (12)
C11—C10—H10120.6C40—C39—H39120.6
C10—C11—C12120.17 (13)C38—C39—H39120.6
C10—C11—H11119.9C39—C40—C41119.04 (12)
C12—C11—H11119.9C39—C40—H40120.5
C11—C12—C7123.14 (13)C41—C40—H40120.5
C11—C12—H12118.4C42—C41—C40118.75 (12)
C7—C12—H12118.4C42—C41—H41120.6
C14—C13—C18115.21 (12)C40—C41—H41120.6
C14—C13—B1123.28 (11)N3—C42—C41122.71 (12)
C18—C13—B1121.50 (11)N3—C42—C43117.21 (11)
C15—C14—C13122.65 (12)C41—C42—C43120.07 (12)
C15—C14—H14118.7N4—C43—C42121.34 (12)
C13—C14—H14118.7N4—C43—H43119.3
C16—C15—C14120.31 (13)C42—C43—H43119.3
C16—C15—H15119.8C50A—C44—N4124.7 (4)
C14—C15—H15119.8C50A—C44—C45123.1 (4)
C15—C16—C17118.90 (13)N4—C44—C45108.20 (11)
C15—C16—H16120.5C50A—C44—C5035.3 (4)
C17—C16—H16120.5N4—C44—C50106.86 (12)
C16—C17—C18120.05 (13)C45—C44—C50114.51 (12)
C16—C17—H17120.0C50A—C44—H44A74.2
C18—C17—H17120.0N4—C44—H44A109.1
C17—C18—C13122.88 (13)C45—C44—H44A109.1
C17—C18—H18118.6C50—C44—H44A109.1
C13—C18—H18118.6C50A—C44—H44B96.6
C24—C19—C20114.93 (12)N4—C44—H44B96.6
C24—C19—B1124.76 (11)C45—C44—H44B96.6
C20—C19—B1120.31 (11)C50—C44—H44B131.4
C21—C20—C19123.25 (12)H44A—C44—H44B22.5
C21—C20—H20118.4C46—C45—C44114.26 (12)
C19—C20—H20118.4C46—C45—H54A108.7
C20—C21—C22119.85 (13)C44—C45—H54A108.7
C20—C21—H21120.1C46—C45—H54B108.7
C22—C21—H21120.1C44—C45—H54B108.7
C23—C22—C21118.86 (12)H54A—C45—H54B107.6
C23—C22—H22120.6C46—C45—H54C108.7
C21—C22—H22120.6C44—C45—H54C108.7
C22—C23—C24120.40 (12)H54A—C45—H54C0.0
C22—C23—H23119.8H54B—C45—H54C107.6
C24—C23—H23119.8C46—C45—H54D108.7
C23—C24—C19122.70 (12)C44—C45—H54D108.7
C23—C24—H24118.7H54A—C45—H54D107.6
C19—C24—H24118.7H54B—C45—H54D0.0
N2—Ag1—N3148.72 (5)H54C—C45—H54D107.6
N2—Ag1—N4137.23 (5)C45—C46—C47113.53 (14)
N3—Ag1—N473.05 (4)C45—C46—H46A108.9
N2—Ag1—N172.93 (4)C47—C46—H46A108.9
N3—Ag1—N1111.61 (4)C45—C46—H46B108.9
N4—Ag1—N1105.16 (4)C47—C46—H46B108.9
N4—Ag1A—N2152.8 (2)H46A—C46—H46B107.7
N4—Ag1A—N1116.27 (16)C48A—C47—C46123.7 (6)
N2—Ag1A—N171.57 (9)C48A—C47—C4819.9 (6)
N4—Ag1A—N374.82 (10)C46—C47—C48116.40 (14)
N2—Ag1A—N3129.94 (19)C48A—C47—H47A88.4
N1—Ag1A—N3106.54 (14)C46—C47—H47A108.2
C25—N1—C29117.62 (12)C48—C47—H47A108.2
C25—N1—Ag1A130.14 (12)C48A—C47—H47B117.5
C29—N1—Ag1A111.44 (11)C46—C47—H47B108.2
C25—N1—Ag1133.29 (10)C48—C47—H47B108.2
C29—N1—Ag1109.08 (8)H47A—C47—H47B107.3
Ag1A—N1—Ag19.44 (9)C48A—C47—H47C106.9
C30—N2—C31117.15 (11)C46—C47—H47C106.5
C30—N2—Ag1117.79 (9)C48—C47—H47C93.6
C31—N2—Ag1124.98 (8)H47A—C47—H47C124.0
C30—N2—Ag1A115.85 (12)H47B—C47—H47C18.5
C31—N2—Ag1A125.32 (11)C48A—C47—H47D105.5
Ag1—N2—Ag1A9.92 (9)C46—C47—H47D106.7
C38—N3—C42117.76 (11)C48—C47—H47D124.4
C38—N3—Ag1127.51 (9)H47A—C47—H47D20.8
C42—N3—Ag1114.56 (9)H47B—C47—H47D88.7
C38—N3—Ag1A136.31 (13)H47C—C47—H47D106.5
C42—N3—Ag1A105.70 (12)C49—C48—C47118.32 (16)
Ag1—N3—Ag1A8.87 (9)C49—C48—H48A107.7
C43—N4—C44119.47 (12)C47—C48—H48A107.7
C43—N4—Ag1A119.45 (14)C49—C48—H48B107.7
C44—N4—Ag1A120.19 (14)C47—C48—H48B107.7
C43—N4—Ag1112.89 (9)H48A—C48—H48B107.1
C44—N4—Ag1127.14 (9)C48—C49—C50117.99 (16)
Ag1A—N4—Ag17.17 (11)C48—C49—H49A107.8
N1—C25—C26123.44 (13)C50—C49—H49A107.8
N1—C25—H25118.3C48—C49—H49B107.8
C26—C25—H25118.3C50—C49—H49B107.8
C27—C26—C25118.38 (12)H49A—C49—H49B107.1
C27—C26—H26120.8C49—C50—C44113.38 (13)
C25—C26—H26120.8C49—C50—H50A108.9
C26—C27—C28119.16 (12)C44—C50—H50A108.9
C26—C27—H27120.4C49—C50—H50B108.9
C28—C27—H27120.4C44—C50—H50B108.9
C27—C28—C29118.46 (12)H50A—C50—H50B107.7
C27—C28—H28120.8C44—C50A—C49A106.1 (7)
C29—C28—H28120.8C44—C50A—H50C110.5
N1—C29—C28122.91 (12)C49A—C50A—H50C110.5
N1—C29—C30117.64 (11)C44—C50A—H50D110.5
C28—C29—C30119.44 (12)C49A—C50A—H50D110.5
N2—C30—C29122.45 (12)H50C—C50A—H50D108.7
N2—C30—H30118.8C48A—C49A—C50A123.0 (10)
C29—C30—H30118.8C48A—C49A—H49C106.6
N2—C31—C37106.57 (11)C50A—C49A—H49C106.6
N2—C31—C32109.93 (11)C48A—C49A—H49D106.6
C37—C31—C32115.82 (11)C50A—C49A—H49D106.6
N2—C31—H31108.1H49C—C49A—H49D106.6
C37—C31—H31108.1C47—C48A—C49A116.1 (9)
C32—C31—H31108.1C47—C48A—H48C108.3
C31—C32—C33116.64 (11)C49A—C48A—H48C108.3
C31—C32—H32A108.1C47—C48A—H48D108.3
C33—C32—H32A108.1C49A—C48A—H48D108.3
C31—C32—H32B108.1H48C—C48A—H48D107.4
C33—C32—H32B108.1
C13—B1—C1—C210.75 (16)N2—Ag1A—N3—C42176.26 (16)
C19—B1—C1—C2107.76 (13)N1—Ag1A—N3—C42104.20 (15)
C7—B1—C1—C2131.28 (12)N4—Ag1A—N3—Ag1168.6 (6)
C13—B1—C1—C6172.15 (11)N2—Ag1A—N3—Ag11.6 (4)
C19—B1—C1—C669.35 (14)N1—Ag1A—N3—Ag177.9 (5)
C7—B1—C1—C651.61 (15)N2—Ag1A—N4—C43168.7 (3)
C6—C1—C2—C30.23 (18)N1—Ag1A—N4—C4390.4 (2)
B1—C1—C2—C3177.05 (12)N3—Ag1A—N4—C4310.82 (14)
C1—C2—C3—C40.3 (2)N2—Ag1A—N4—C4422.2 (4)
C2—C3—C4—C50.37 (19)N1—Ag1A—N4—C4478.70 (19)
C3—C4—C5—C60.00 (19)N3—Ag1A—N4—C44179.94 (10)
C4—C5—C6—C10.52 (19)N2—Ag1A—N4—Ag1144.2 (11)
C2—C1—C6—C50.61 (18)N1—Ag1A—N4—Ag1115.0 (9)
B1—C1—C6—C5176.73 (11)N3—Ag1A—N4—Ag113.7 (8)
C1—B1—C7—C87.04 (17)N2—Ag1—N4—C43178.67 (9)
C13—B1—C7—C8114.34 (13)N3—Ag1—N4—C438.19 (9)
C19—B1—C7—C8127.93 (13)N1—Ag1—N4—C43100.25 (10)
C1—B1—C7—C12175.64 (11)N2—Ag1—N4—C449.61 (14)
C13—B1—C7—C1262.98 (14)N3—Ag1—N4—C44179.92 (11)
C19—B1—C7—C1254.75 (14)N1—Ag1—N4—C4471.48 (11)
C12—C7—C8—C91.03 (18)N2—Ag1—N4—Ag1A24.4 (8)
B1—C7—C8—C9178.47 (12)N3—Ag1—N4—Ag1A165.1 (8)
C7—C8—C9—C100.5 (2)N1—Ag1—N4—Ag1A56.6 (8)
C8—C9—C10—C110.4 (2)C29—N1—C25—C260.1 (2)
C9—C10—C11—C120.6 (2)Ag1A—N1—C25—C26168.83 (17)
C10—C11—C12—C70.0 (2)Ag1—N1—C25—C26179.24 (10)
C8—C7—C12—C110.77 (19)N1—C25—C26—C270.9 (2)
B1—C7—C12—C11178.37 (12)C25—C26—C27—C280.8 (2)
C1—B1—C13—C14103.12 (13)C26—C27—C28—C290.1 (2)
C19—B1—C13—C14137.73 (12)C25—N1—C29—C281.1 (2)
C7—B1—C13—C1419.25 (16)Ag1A—N1—C29—C28171.90 (15)
C1—B1—C13—C1875.83 (14)Ag1—N1—C29—C28178.35 (11)
C19—B1—C13—C1843.33 (15)C25—N1—C29—C30177.69 (12)
C7—B1—C13—C18161.80 (11)Ag1A—N1—C29—C306.92 (18)
C18—C13—C14—C150.65 (19)Ag1—N1—C29—C302.82 (14)
B1—C13—C14—C15178.36 (12)C27—C28—C29—N11.2 (2)
C13—C14—C15—C160.9 (2)C27—C28—C29—C30177.64 (12)
C14—C15—C16—C170.5 (2)C31—N2—C30—C29174.87 (12)
C15—C16—C17—C180.1 (2)Ag1—N2—C30—C292.10 (17)
C16—C17—C18—C130.4 (2)Ag1A—N2—C30—C298.8 (2)
C14—C13—C18—C170.00 (19)N1—C29—C30—N20.8 (2)
B1—C13—C18—C17179.03 (12)C28—C29—C30—N2179.70 (13)
C1—B1—C19—C2420.96 (16)C30—N2—C31—C3792.35 (14)
C13—B1—C19—C24140.62 (12)Ag1—N2—C31—C3784.38 (12)
C7—B1—C19—C24101.40 (14)Ag1A—N2—C31—C3772.25 (18)
C1—B1—C19—C20159.69 (11)C30—N2—C31—C32141.41 (12)
C13—B1—C19—C2040.03 (15)Ag1—N2—C31—C3241.87 (14)
C7—B1—C19—C2077.95 (14)Ag1A—N2—C31—C3254.00 (19)
C24—C19—C20—C211.25 (19)N2—C31—C32—C3387.85 (14)
B1—C19—C20—C21178.16 (12)C37—C31—C32—C3332.98 (17)
C19—C20—C21—C221.7 (2)C31—C32—C33—C3484.03 (15)
C20—C21—C22—C230.8 (2)C32—C33—C34—C3572.20 (16)
C21—C22—C23—C240.4 (2)C33—C34—C35—C3654.07 (18)
C22—C23—C24—C190.8 (2)C34—C35—C36—C3769.82 (16)
C20—C19—C24—C230.01 (19)N2—C31—C37—C36167.12 (11)
B1—C19—C24—C23179.37 (12)C32—C31—C37—C3644.50 (17)
N4—Ag1A—N1—C2525.6 (3)C35—C36—C37—C3188.65 (15)
N2—Ag1A—N1—C25177.30 (14)C42—N3—C38—C390.16 (19)
N3—Ag1A—N1—C2555.3 (2)Ag1—N3—C38—C39174.86 (10)
N4—Ag1A—N1—C29143.70 (16)Ag1A—N3—C38—C39173.28 (14)
N2—Ag1A—N1—C298.02 (15)N3—C38—C39—C400.9 (2)
N3—Ag1A—N1—C29135.39 (13)C38—C39—C40—C410.9 (2)
N4—Ag1A—N1—Ag1139.0 (6)C39—C40—C41—C420.08 (19)
N2—Ag1A—N1—Ag169.3 (5)C38—N3—C42—C411.19 (18)
N3—Ag1A—N1—Ag158.1 (5)Ag1—N3—C42—C41174.47 (10)
N2—Ag1—N1—C25177.82 (15)Ag1A—N3—C42—C41174.10 (13)
N3—Ag1—N1—C2535.04 (15)C38—N3—C42—C43177.52 (11)
N4—Ag1—N1—C2542.39 (14)Ag1—N3—C42—C436.81 (14)
N2—Ag1—N1—C292.80 (9)Ag1A—N3—C42—C437.18 (15)
N3—Ag1—N1—C29144.33 (9)C40—C41—C42—N31.2 (2)
N4—Ag1—N1—C29138.23 (9)C40—C41—C42—C43177.52 (12)
N2—Ag1—N1—Ag1A103.3 (5)C44—N4—C43—C42179.68 (11)
N3—Ag1—N1—Ag1A109.6 (5)Ag1A—N4—C43—C4211.1 (2)
N4—Ag1—N1—Ag1A32.1 (5)Ag1—N4—C43—C427.90 (16)
N3—Ag1—N2—C30101.11 (13)N3—C42—C43—N40.98 (18)
N4—Ag1—N2—C3096.63 (11)C41—C42—C43—N4177.77 (12)
N1—Ag1—N2—C302.57 (10)C43—N4—C44—C50A108.7 (5)
N3—Ag1—N2—C3182.18 (13)Ag1A—N4—C44—C50A60.4 (5)
N4—Ag1—N2—C3180.08 (12)Ag1—N4—C44—C50A62.5 (5)
N1—Ag1—N2—C31174.14 (11)C43—N4—C44—C4593.33 (15)
N3—Ag1—N2—Ag1A177.6 (6)Ag1A—N4—C44—C4597.55 (16)
N4—Ag1—N2—Ag1A15.4 (5)Ag1—N4—C44—C4595.43 (13)
N1—Ag1—N2—Ag1A78.7 (5)C43—N4—C44—C50142.90 (13)
N4—Ag1A—N2—C30103.1 (4)Ag1A—N4—C44—C5026.22 (17)
N1—Ag1A—N2—C308.72 (15)Ag1—N4—C44—C5028.34 (15)
N3—Ag1A—N2—C30105.17 (19)C50A—C44—C45—C4621.7 (5)
N4—Ag1A—N2—C3161.6 (4)N4—C44—C45—C46179.86 (13)
N1—Ag1A—N2—C31173.49 (11)C50—C44—C45—C4661.11 (17)
N3—Ag1A—N2—C3190.1 (2)C44—C45—C46—C4776.13 (17)
N4—Ag1A—N2—Ag1153.2 (8)C45—C46—C47—C48A61.1 (8)
N1—Ag1A—N2—Ag195.0 (5)C45—C46—C47—C4882.50 (18)
N3—Ag1A—N2—Ag11.5 (4)C48A—C47—C48—C4982.3 (16)
N2—Ag1—N3—C389.59 (16)C46—C47—C48—C4934.4 (2)
N4—Ag1—N3—C38177.09 (11)C47—C48—C49—C5038.3 (3)
N1—Ag1—N3—C3882.93 (11)C48—C49—C50—C4482.40 (19)
N2—Ag1—N3—C42175.25 (9)C50A—C44—C50—C4940.5 (7)
N4—Ag1—N3—C427.75 (9)N4—C44—C50—C49167.58 (13)
N1—Ag1—N3—C4292.23 (9)C45—C44—C50—C4972.63 (17)
N2—Ag1—N3—Ag1A177.5 (6)N4—C44—C50A—C49A102.4 (7)
N4—Ag1—N3—Ag1A10.0 (5)C45—C44—C50A—C49A52.4 (9)
N1—Ag1—N3—Ag1A90.0 (6)C50—C44—C50A—C49A34.0 (5)
N4—Ag1A—N3—C38176.78 (13)C44—C50A—C49A—C48A87.5 (12)
N2—Ag1A—N3—C389.8 (3)C46—C47—C48A—C49A31.6 (15)
N1—Ag1A—N3—C3869.8 (2)C48—C47—C48A—C49A106 (2)
N4—Ag1A—N3—C429.25 (12)C50A—C49A—C48A—C4754.7 (17)
Table 1
Selected geometric parameters (Å, °)
top
Ag1—N22.2025 (12)Ag1A—N42.045 (4)
Ag1—N32.2757 (12)Ag1A—N22.310 (3)
Ag1—N42.3426 (13)Ag1A—N12.444 (3)
Ag1—N12.4646 (12)Ag1A—N32.449 (4)
N2—Ag1—N3148.72 (5)N4—Ag1A—N2152.8 (2)
N2—Ag1—N4137.23 (5)N4—Ag1A—N1116.27 (16)
N3—Ag1—N473.05 (4)N2—Ag1A—N171.57 (9)
N2—Ag1—N172.93 (4)N4—Ag1A—N374.82 (10)
N3—Ag1—N1111.61 (4)N2—Ag1A—N3129.94 (19)
N4—Ag1—N1105.16 (4)N1—Ag1A—N3106.54 (14)
Acknowledgements top

SD acknowledges the Alzahra University Research Council for partial support of this work.

references
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