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Acta Cryst. (2008). E64, m158    [ doi:10.1107/S1600536807064239 ]

(Triphenylphosphine-[kappa]P)[tris(indazol-1-yl)borato-[kappa]3N,N',N'']silver(I)

M. H. Sadr, S. A. Niaz, S. Gorbani, S. Gao and S. W. Ng

Abstract top

The phosphine-coordinated AgI atom in the title compound, [Ag(C21H17BN6)(C18H15P)], is also N,N',N''-chelated by the tris(indazolyl)borate anion. The resultant N3P coordination geometry is tetrahedral.

Comment top

Hydrotris(indazolyl)borate, Tp4Bo, is suggested to be a suitable tripodal ligand for supramolecular assembly (Janiak et al., 2000). In the title silver derivative, Ag(C21H17N6B)(C18H15P), the Tp4Bo anion functions as a tridentate ligand (Fig. 1). The triphenylphosphine ligand completes the N3P coordination geometry for Ag. The Ag center is tetrahedrally coordinated, but the N–Ag–N angles are significantly less than 90°, i.e. range from 82.3 (1) to 83.8 (2)°.

Related literature top

For related literature; see Janiak et al. (2000).

Experimental top

Under a dry nitrogen atmosphere, K[HB(Indazolyl)3] (0.2 g, 1 mmol) was added to a mixture of AgNO3 (0.17 g, 1 mmol) and PPh3 (0.26 g, 2 mmol) in methanol (40 ml). After being stirred for 3 h, the colorless solution was filtered. Crystals were obtained from the filtrate after a week.

Refinement top

The H atoms were included in the refinement in the riding model approximation with = C–H 0.93, and with U(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing atom numbering scheme, displacement ellipsoids at the 50% probability level and H atoms as spheres of arbitrary radii.
(Triphenylphosphine-κP)[tris(indazol-1-yl)borato- κ3N,\<i>N',N'']silver(I) top
Crystal data top
[Ag(C21H17BN6)(C18H15P)]Z = 2
Mr = 734.36F(000) = 750
Triclinic, P1Dx = 1.392 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2950 (6) ÅCell parameters from 10642 reflections
b = 12.6644 (6) Åθ = 3.0–27.5°
c = 13.9555 (7) ŵ = 0.66 mm−1
α = 87.003 (1)°T = 295 K
β = 77.966 (2)°Block, colorless
γ = 79.903 (1)°0.31 × 0.28 × 0.15 mm
V = 1751.7 (2) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		7925 independent reflections
Radiation source: fine-focus sealed tube4255 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −13→13
Tmin = 0.551, Tmax = 0.908k = −16→14
17380 measured reflectionsl = −18→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0652P)2 + 1.2113P]
where P = (Fo2 + 2Fc2)/3
7925 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.87 e Å−3
0 restraintsΔρmin = −0.95 e Å−3
Crystal data top
[Ag(C21H17BN6)(C18H15P)]γ = 79.903 (1)°
Mr = 734.36V = 1751.7 (2) Å3
Triclinic, P1Z = 2
a = 10.2950 (6) ÅMo Kα radiation
b = 12.6644 (6) ŵ = 0.66 mm−1
c = 13.9555 (7) ÅT = 295 K
α = 87.003 (1)°0.31 × 0.28 × 0.15 mm
β = 77.966 (2)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		7925 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4255 reflections with I > 2σ(I)
Tmin = 0.551, Tmax = 0.908Rint = 0.038
17380 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.159Δρmax = 0.87 e Å−3
S = 1.08Δρmin = −0.95 e Å−3
7925 reflectionsAbsolute structure: ?
433 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.46371 (4)0.69276 (3)0.81804 (3)0.06680 (17)
P10.28241 (12)0.80700 (9)0.90871 (9)0.0525 (3)
N10.5981 (4)0.7791 (3)0.6910 (3)0.0682 (11)
N20.7025 (4)0.7136 (3)0.6353 (3)0.0587 (9)
N30.4898 (4)0.5627 (3)0.7017 (3)0.0660 (11)
N40.6162 (4)0.5350 (3)0.6461 (3)0.0610 (10)
N50.6709 (4)0.5973 (3)0.8415 (3)0.0637 (10)
N60.7627 (4)0.5686 (3)0.7583 (3)0.0590 (9)
C10.6028 (6)0.8787 (4)0.6578 (4)0.0772 (15)
H10.54220.93860.68370.093*
C20.7101 (6)0.8818 (4)0.5794 (4)0.0704 (14)
C30.7642 (8)0.9632 (6)0.5185 (5)0.105 (2)
H30.72411.03490.52600.126*
C40.8754 (10)0.9333 (8)0.4497 (6)0.132 (3)
H40.91400.98580.41020.158*
C50.9350 (8)0.8255 (8)0.4357 (6)0.125 (3)
H51.01010.80800.38560.150*
C60.8851 (6)0.7453 (6)0.4941 (4)0.0890 (17)
H60.92530.67390.48490.107*
C70.7729 (5)0.7747 (4)0.5670 (4)0.0638 (12)
C80.4152 (6)0.4946 (4)0.6823 (4)0.0736 (14)
H80.32450.49710.71010.088*
C90.4908 (6)0.4181 (4)0.6143 (4)0.0672 (13)
C100.4641 (8)0.3292 (5)0.5697 (5)0.0900 (19)
H100.37850.31080.58280.108*
C110.5667 (10)0.2717 (5)0.5075 (5)0.104 (2)
H110.55110.21260.47740.125*
C120.6947 (9)0.2981 (5)0.4871 (4)0.100 (2)
H120.76270.25560.44420.120*
C130.7254 (7)0.3861 (4)0.5285 (4)0.0816 (17)
H130.75890.43370.47600.098*
H13B0.79770.36090.56320.098*
C140.6182 (6)0.4457 (4)0.5935 (3)0.0615 (12)
C150.7202 (6)0.5533 (4)0.9166 (4)0.0696 (13)
H150.67590.56140.98170.083*
C160.8488 (5)0.4923 (4)0.8855 (4)0.0686 (13)
C170.9442 (6)0.4265 (4)0.9313 (5)0.0844 (17)
H170.92910.41680.99900.101*
C181.0592 (7)0.3777 (5)0.8726 (7)0.101 (2)
H181.12320.33330.90110.121*
C191.0845 (6)0.3920 (5)0.7716 (6)0.096 (2)
H191.16550.35840.73440.115*
C200.9923 (5)0.4547 (4)0.7253 (5)0.0768 (15)
H201.00930.46370.65750.092*
C210.8725 (5)0.5043 (3)0.7836 (4)0.0619 (12)
C220.1187 (5)0.7991 (3)0.8834 (3)0.0576 (11)
C230.1166 (6)0.7634 (5)0.7923 (4)0.0804 (15)
H230.19730.74140.74860.096*
C24−0.0051 (7)0.7600 (6)0.7647 (5)0.099 (2)
H24−0.00470.73640.70270.119*
C25−0.1241 (7)0.7907 (5)0.8274 (5)0.0873 (17)
H25−0.20530.79020.80830.105*
C26−0.1224 (5)0.8227 (5)0.9196 (5)0.0811 (16)
H26−0.20330.84130.96400.097*
C27−0.0024 (5)0.8276 (4)0.9475 (4)0.0654 (12)
H27−0.00340.85041.01000.079*
C280.3049 (4)0.9449 (3)0.8736 (3)0.0495 (10)
C290.2260 (6)1.0098 (4)0.8192 (4)0.0774 (15)
H290.15120.98710.80480.093*
C300.2568 (7)1.1094 (4)0.7852 (5)0.094 (2)
H300.20431.15160.74610.113*
C310.3624 (7)1.1457 (4)0.8083 (5)0.0825 (16)
H310.38131.21300.78650.099*
C320.4409 (6)1.0826 (4)0.8639 (4)0.0731 (14)
H320.51351.10710.88010.088*
C330.4127 (5)0.9823 (4)0.8963 (4)0.0626 (12)
H330.46700.93960.93380.075*
C340.2676 (5)0.8030 (4)1.0407 (3)0.0563 (11)
C350.3329 (5)0.7129 (4)1.0828 (4)0.0667 (13)
H350.37930.65581.04350.080*
C360.3300 (7)0.7069 (5)1.1818 (5)0.0879 (18)
H360.37390.64581.20900.105*
C370.2629 (7)0.7904 (6)1.2403 (4)0.093 (2)
H370.26150.78611.30720.111*
C380.1973 (6)0.8808 (6)1.2007 (4)0.0872 (17)
H380.15170.93761.24080.105*
C390.1992 (5)0.8872 (4)1.1014 (4)0.0692 (13)
H390.15450.94841.07490.083*
B10.7306 (5)0.5929 (4)0.6564 (4)0.0608 (14)
H1B0.81050.56240.60840.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0566 (2)0.0586 (2)0.0756 (3)−0.00108 (16)0.00227 (18)−0.00611 (17)
P10.0478 (7)0.0523 (6)0.0537 (7)−0.0065 (5)−0.0036 (5)−0.0012 (5)
N10.068 (3)0.059 (2)0.066 (3)−0.0076 (19)0.008 (2)−0.0010 (19)
N20.054 (2)0.064 (2)0.055 (2)−0.0135 (18)−0.0013 (18)−0.0005 (18)
N30.060 (3)0.060 (2)0.079 (3)−0.0117 (19)−0.013 (2)−0.010 (2)
N40.061 (3)0.059 (2)0.062 (2)−0.0072 (18)−0.013 (2)−0.0086 (19)
N50.056 (2)0.066 (2)0.064 (2)0.0058 (18)−0.014 (2)−0.0028 (19)
N60.045 (2)0.065 (2)0.064 (2)−0.0014 (17)−0.0100 (19)−0.0067 (18)
C10.089 (4)0.055 (3)0.079 (4)−0.007 (3)−0.001 (3)−0.001 (3)
C20.075 (4)0.076 (3)0.059 (3)−0.024 (3)−0.003 (3)0.004 (2)
C30.130 (6)0.096 (5)0.083 (4)−0.035 (4)0.003 (4)0.012 (4)
C40.143 (8)0.134 (7)0.112 (6)−0.054 (6)0.008 (6)0.034 (5)
C50.104 (6)0.160 (8)0.093 (5)−0.036 (5)0.029 (4)0.018 (5)
C60.075 (4)0.107 (4)0.075 (4)−0.016 (3)0.007 (3)−0.003 (3)
C70.057 (3)0.078 (3)0.058 (3)−0.016 (2)−0.009 (2)−0.006 (2)
C80.065 (3)0.069 (3)0.091 (4)−0.014 (3)−0.025 (3)0.003 (3)
C90.083 (4)0.063 (3)0.066 (3)−0.017 (3)−0.037 (3)0.004 (2)
C100.125 (6)0.076 (4)0.085 (4)−0.027 (4)−0.052 (4)0.002 (3)
C110.165 (8)0.081 (4)0.085 (5)−0.029 (5)−0.058 (5)−0.008 (4)
C120.153 (7)0.083 (4)0.060 (4)0.002 (4)−0.027 (4)−0.021 (3)
C130.117 (5)0.078 (3)0.046 (3)0.001 (3)−0.023 (3)−0.001 (3)
C140.080 (4)0.057 (3)0.050 (3)−0.004 (2)−0.026 (3)0.000 (2)
C150.073 (4)0.064 (3)0.072 (3)−0.009 (3)−0.019 (3)−0.004 (2)
C160.069 (3)0.051 (3)0.092 (4)−0.014 (2)−0.027 (3)0.003 (3)
C170.087 (4)0.066 (3)0.109 (5)−0.015 (3)−0.041 (4)0.013 (3)
C180.074 (4)0.077 (4)0.153 (7)−0.003 (3)−0.039 (5)0.017 (4)
C190.061 (4)0.070 (4)0.147 (7)0.003 (3)−0.011 (4)0.004 (4)
C200.058 (3)0.067 (3)0.102 (4)−0.004 (2)−0.011 (3)−0.005 (3)
C210.051 (3)0.049 (2)0.088 (4)−0.011 (2)−0.016 (3)−0.004 (2)
C220.070 (3)0.051 (2)0.052 (3)−0.016 (2)−0.008 (2)0.000 (2)
C230.073 (4)0.103 (4)0.069 (4)−0.024 (3)−0.011 (3)−0.018 (3)
C240.100 (5)0.127 (5)0.085 (4)−0.036 (4)−0.035 (4)−0.024 (4)
C250.084 (4)0.085 (4)0.107 (5)−0.028 (3)−0.038 (4)−0.005 (4)
C260.045 (3)0.088 (4)0.110 (5)−0.019 (3)−0.006 (3)−0.006 (3)
C270.055 (3)0.074 (3)0.067 (3)−0.012 (2)−0.008 (2)−0.010 (2)
C280.044 (2)0.057 (2)0.046 (2)−0.0053 (18)−0.0074 (19)−0.0032 (18)
C290.079 (4)0.065 (3)0.098 (4)−0.014 (3)−0.041 (3)0.009 (3)
C300.104 (5)0.062 (3)0.132 (6)−0.022 (3)−0.060 (4)0.026 (3)
C310.098 (4)0.058 (3)0.095 (4)−0.022 (3)−0.025 (4)0.019 (3)
C320.074 (4)0.074 (3)0.075 (3)−0.032 (3)−0.008 (3)0.002 (3)
C330.057 (3)0.073 (3)0.059 (3)−0.018 (2)−0.012 (2)0.005 (2)
C340.051 (3)0.062 (3)0.056 (3)−0.014 (2)−0.008 (2)0.004 (2)
C350.070 (3)0.060 (3)0.075 (3)−0.019 (2)−0.021 (3)0.014 (2)
C360.099 (5)0.096 (4)0.081 (4)−0.040 (4)−0.036 (4)0.032 (4)
C370.096 (5)0.136 (6)0.057 (3)−0.055 (4)−0.019 (3)0.022 (4)
C380.077 (4)0.125 (5)0.057 (3)−0.023 (4)0.000 (3)−0.006 (3)
C390.064 (3)0.081 (3)0.060 (3)−0.011 (3)−0.009 (3)0.003 (3)
B10.041 (3)0.071 (3)0.068 (4)−0.003 (2)−0.006 (3)−0.014 (3)
Geometric parameters (Å, °) top
Ag1—N12.358 (4)C15—H150.9300
Ag1—N32.316 (4)C16—C211.397 (7)
Ag1—N52.337 (4)C16—C171.410 (7)
Ag1—P12.332 (1)C17—C181.359 (9)
P1—C221.814 (5)C17—H170.9300
P1—C341.814 (5)C18—C191.387 (10)
P1—C281.830 (4)C18—H180.9300
N1—C11.326 (6)C19—C201.373 (8)
N1—N21.361 (5)C19—H190.9300
N2—C71.365 (6)C20—C211.394 (7)
N2—B11.529 (7)C20—H200.9300
N3—C81.322 (6)C22—C271.377 (7)
N3—N41.366 (5)C22—C231.377 (7)
N4—C141.375 (6)C23—C241.393 (8)
N4—B11.526 (7)C23—H230.9300
N5—C151.316 (6)C24—C251.356 (9)
N5—N61.356 (5)C24—H240.9300
N6—C211.370 (6)C25—C261.373 (8)
N6—B11.531 (7)C25—H250.9300
C1—C21.388 (7)C26—C271.383 (7)
C1—H10.9300C26—H260.9300
C2—C71.400 (7)C27—H270.9300
C2—C31.416 (8)C28—C291.368 (6)
C3—C41.343 (11)C28—C331.379 (6)
C3—H30.9300C29—C301.390 (7)
C4—C51.401 (11)C29—H290.9300
C4—H40.9300C30—C311.354 (8)
C5—C61.372 (9)C30—H300.9300
C5—H50.9300C31—C321.365 (8)
C6—C71.382 (7)C31—H310.9300
C6—H60.9300C32—C331.385 (7)
C8—C91.403 (7)C32—H320.9300
C8—H80.9300C33—H330.9300
C9—C141.386 (7)C34—C391.391 (7)
C9—C101.408 (7)C34—C351.387 (6)
C10—C111.347 (10)C35—C361.374 (8)
C10—H100.9300C35—H350.9300
C11—C121.385 (10)C36—C371.364 (9)
C11—H110.9300C36—H360.9300
C12—C131.394 (8)C37—C381.376 (9)
C12—H120.9300C37—H370.9300
C13—C141.404 (7)C38—C391.380 (7)
C13—H130.9700C38—H380.9300
C13—H13B0.9700C39—H390.9300
C15—C161.405 (7)B1—H1B0.9800
N1—Ag1—N383.8 (2)C21—C16—C15103.7 (4)
N1—Ag1—N583.7 (2)C21—C16—C17120.4 (5)
N1—Ag1—P1114.3 (1)C15—C16—C17135.8 (6)
N3—Ag1—N582.3 (1)C18—C17—C16117.3 (6)
N3—Ag1—P1135.6 (1)C18—C17—H17121.3
N5—Ag1—P1137.2 (1)C16—C17—H17121.3
C22—P1—C34108.0 (2)C17—C18—C19122.3 (6)
C22—P1—C28103.7 (2)C17—C18—H18118.9
C34—P1—C28104.0 (2)C19—C18—H18118.9
C22—P1—Ag1115.48 (15)C20—C19—C18121.4 (6)
C34—P1—Ag1116.65 (15)C20—C19—H19119.3
C28—P1—Ag1107.61 (14)C18—C19—H19119.3
C1—N1—N2107.6 (4)C19—C20—C21117.5 (6)
C1—N1—Ag1137.0 (3)C19—C20—H20121.2
N2—N1—Ag1115.3 (3)C21—C20—H20121.2
N1—N2—C7108.7 (4)N6—C21—C20130.5 (5)
N1—N2—B1121.5 (4)N6—C21—C16108.5 (4)
C7—N2—B1129.7 (4)C20—C21—C16121.0 (5)
C8—N3—N4107.6 (4)C27—C22—C23118.2 (5)
C8—N3—Ag1135.3 (4)C27—C22—P1124.9 (4)
N4—N3—Ag1116.4 (3)C23—C22—P1116.9 (4)
N3—N4—C14108.3 (4)C22—C23—C24120.7 (6)
N3—N4—B1121.1 (4)C22—C23—H23119.6
C14—N4—B1130.3 (4)C24—C23—H23119.6
C15—N5—N6108.3 (4)C25—C24—C23120.8 (6)
C15—N5—Ag1136.0 (4)C25—C24—H24119.6
N6—N5—Ag1115.3 (3)C23—C24—H24119.6
N5—N6—C21108.4 (4)C24—C25—C26118.7 (6)
N5—N6—B1122.2 (4)C24—C25—H25120.7
C21—N6—B1128.7 (4)C26—C25—H25120.7
N1—C1—C2111.2 (5)C27—C26—C25121.2 (6)
N1—C1—H1124.4C27—C26—H26119.4
C2—C1—H1124.4C25—C26—H26119.4
C1—C2—C7104.3 (4)C22—C27—C26120.4 (5)
C1—C2—C3135.7 (6)C22—C27—H27119.8
C7—C2—C3120.0 (6)C26—C27—H27119.8
C4—C3—C2117.7 (7)C29—C28—C33118.3 (4)
C4—C3—H3121.2C29—C28—P1122.9 (4)
C2—C3—H3121.2C33—C28—P1118.6 (3)
C3—C4—C5121.9 (7)C28—C29—C30120.5 (5)
C3—C4—H4119.0C28—C29—H29119.7
C5—C4—H4119.0C30—C29—H29119.7
C6—C5—C4121.5 (7)C31—C30—C29120.7 (5)
C6—C5—H5119.3C31—C30—H30119.7
C4—C5—H5119.3C29—C30—H30119.7
C5—C6—C7117.5 (6)C30—C31—C32119.5 (5)
C5—C6—H6121.3C30—C31—H31120.2
C7—C6—H6121.3C32—C31—H31120.2
N2—C7—C6130.4 (5)C31—C32—C33120.1 (5)
N2—C7—C2108.2 (4)C31—C32—H32119.9
C6—C7—C2121.4 (5)C33—C32—H32119.9
N3—C8—C9111.3 (5)C28—C33—C32120.8 (5)
N3—C8—H8124.4C28—C33—H33119.6
C9—C8—H8124.4C32—C33—H33119.6
C14—C9—C8104.1 (4)C39—C34—C35118.1 (5)
C14—C9—C10120.7 (6)C39—C34—P1123.5 (4)
C8—C9—C10135.2 (6)C35—C34—P1118.3 (4)
C11—C10—C9117.8 (7)C36—C35—C34121.0 (5)
C11—C10—H10121.1C36—C35—H35119.5
C9—C10—H10121.1C34—C35—H35119.5
C10—C11—C12121.8 (6)C37—C36—C35120.1 (6)
C10—C11—H11119.1C37—C36—H36119.9
C12—C11—H11119.1C35—C36—H36119.9
C11—C12—C13122.4 (6)C36—C37—C38120.3 (6)
C11—C12—H12118.8C36—C37—H37119.9
C13—C12—H12118.8C38—C37—H37119.9
C12—C13—C14115.6 (6)C39—C38—C37119.9 (6)
C12—C13—H13108.4C39—C38—H38120.0
C14—C13—H13108.4C37—C38—H38120.0
C12—C13—H13B108.4C38—C39—C34120.5 (5)
C14—C13—H13B108.4C38—C39—H39119.7
H13—C13—H13B107.4C34—C39—H39119.7
N4—C14—C9108.8 (4)N4—B1—N2113.6 (4)
N4—C14—C13129.6 (5)N4—B1—N6108.9 (4)
C9—C14—C13121.7 (5)N2—B1—N6111.7 (4)
N5—C15—C16111.0 (5)N4—B1—H1B107.4
N5—C15—H15124.5N2—B1—H1B107.4
C16—C15—H15124.5N6—B1—H1B107.4
N3—Ag1—P1—C22−2.1 (2)C12—C13—C14—N4179.4 (5)
N5—Ag1—P1—C22−147.2 (2)C12—C13—C14—C9−0.2 (7)
N1—Ag1—P1—C22104.8 (2)N6—N5—C15—C16−0.2 (6)
N3—Ag1—P1—C34126.3 (2)Ag1—N5—C15—C16171.9 (3)
N5—Ag1—P1—C34−18.7 (2)N5—C15—C16—C210.2 (6)
N1—Ag1—P1—C34−126.8 (2)N5—C15—C16—C17−177.2 (6)
N3—Ag1—P1—C28−117.4 (2)C21—C16—C17—C181.1 (8)
N5—Ag1—P1—C2897.6 (2)C15—C16—C17—C18178.1 (6)
N1—Ag1—P1—C28−10.5 (2)C16—C17—C18—C190.7 (10)
N3—Ag1—N1—C1141.2 (6)C17—C18—C19—C20−1.5 (11)
P1—Ag1—N1—C13.5 (6)C18—C19—C20—C210.5 (9)
N5—Ag1—N1—C1−136.0 (6)N5—N6—C21—C20179.9 (5)
N3—Ag1—N1—N2−40.6 (3)B1—N6—C21—C209.3 (8)
P1—Ag1—N1—N2−178.3 (3)N5—N6—C21—C160.1 (5)
N5—Ag1—N1—N242.2 (3)B1—N6—C21—C16−170.5 (5)
C1—N1—N2—C70.4 (6)C19—C20—C21—N6−178.5 (5)
Ag1—N1—N2—C7−178.4 (3)C19—C20—C21—C161.3 (8)
C1—N1—N2—B1177.5 (5)C15—C16—C21—N6−0.1 (5)
Ag1—N1—N2—B1−1.2 (5)C17—C16—C21—N6177.7 (4)
P1—Ag1—N3—C8−29.4 (6)C15—C16—C21—C20180.0 (5)
N5—Ag1—N3—C8127.4 (5)C17—C16—C21—C20−2.1 (7)
N1—Ag1—N3—C8−148.1 (5)C34—P1—C22—C2723.4 (5)
P1—Ag1—N3—N4161.9 (2)C28—P1—C22—C27−86.5 (4)
N5—Ag1—N3—N4−41.2 (3)Ag1—P1—C22—C27156.0 (4)
N1—Ag1—N3—N443.3 (3)C34—P1—C22—C23−157.7 (4)
C8—N3—N4—C14−1.6 (5)C28—P1—C22—C2392.4 (4)
Ag1—N3—N4—C14170.0 (3)Ag1—P1—C22—C23−25.1 (4)
C8—N3—N4—B1−175.6 (4)C27—C22—C23—C242.3 (8)
Ag1—N3—N4—B1−3.9 (5)P1—C22—C23—C24−176.7 (5)
N3—Ag1—N5—C15−127.3 (5)C22—C23—C24—C25−0.7 (10)
P1—Ag1—N5—C1528.9 (6)C23—C24—C25—C26−1.7 (10)
N1—Ag1—N5—C15148.2 (5)C24—C25—C26—C272.5 (9)
N3—Ag1—N5—N644.4 (3)C23—C22—C27—C26−1.5 (7)
P1—Ag1—N5—N6−159.5 (2)P1—C22—C27—C26177.4 (4)
N1—Ag1—N5—N6−40.2 (3)C25—C26—C27—C22−0.9 (8)
C15—N5—N6—C210.1 (5)C22—P1—C28—C29−14.0 (5)
Ag1—N5—N6—C21−173.8 (3)C34—P1—C28—C29−126.8 (4)
C15—N5—N6—B1171.4 (4)Ag1—P1—C28—C29108.8 (4)
Ag1—N5—N6—B1−2.5 (5)C22—P1—C28—C33171.2 (4)
N2—N1—C1—C20.1 (7)C34—P1—C28—C3358.4 (4)
Ag1—N1—C1—C2178.4 (4)Ag1—P1—C28—C33−65.9 (4)
N1—C1—C2—C7−0.4 (7)C33—C28—C29—C302.1 (8)
N1—C1—C2—C3−178.4 (7)P1—C28—C29—C30−172.7 (5)
C1—C2—C3—C4178.1 (8)C28—C29—C30—C31−2.5 (10)
C7—C2—C3—C40.4 (10)C29—C30—C31—C321.4 (10)
C2—C3—C4—C51.8 (14)C30—C31—C32—C330.1 (9)
C3—C4—C5—C6−2.3 (15)C29—C28—C33—C32−0.7 (7)
C4—C5—C6—C70.5 (12)P1—C28—C33—C32174.4 (4)
N1—N2—C7—C6−179.3 (6)C31—C32—C33—C28−0.4 (8)
B1—N2—C7—C63.8 (9)C22—P1—C34—C39−71.4 (5)
N1—N2—C7—C2−0.6 (6)C28—P1—C34—C3938.3 (5)
B1—N2—C7—C2−177.5 (5)Ag1—P1—C34—C39156.6 (4)
C5—C6—C7—N2−179.8 (6)C22—P1—C34—C35111.5 (4)
C5—C6—C7—C21.7 (9)C28—P1—C34—C35−138.7 (4)
C1—C2—C7—N20.6 (6)Ag1—P1—C34—C35−20.5 (4)
C3—C2—C7—N2179.0 (5)C39—C34—C35—C360.1 (8)
C1—C2—C7—C6179.4 (5)P1—C34—C35—C36177.3 (4)
C3—C2—C7—C6−2.2 (9)C34—C35—C36—C37−0.3 (9)
N4—N3—C8—C91.1 (6)C35—C36—C37—C380.2 (10)
Ag1—N3—C8—C9−168.2 (3)C36—C37—C38—C390.1 (10)
N3—C8—C9—C14−0.2 (6)C37—C38—C39—C34−0.3 (9)
N3—C8—C9—C10179.2 (6)C35—C34—C39—C380.2 (8)
C14—C9—C10—C110.8 (8)P1—C34—C39—C38−176.9 (4)
C8—C9—C10—C11−178.6 (6)N3—N4—B1—N2−59.2 (6)
C9—C10—C11—C12−0.1 (9)C14—N4—B1—N2128.3 (5)
C10—C11—C12—C13−0.7 (10)N3—N4—B1—N666.0 (5)
C11—C12—C13—C140.8 (9)C14—N4—B1—N6−106.5 (5)
N3—N4—C14—C91.5 (5)N1—N2—B1—N462.3 (6)
B1—N4—C14—C9174.7 (5)C7—N2—B1—N4−121.2 (5)
N3—N4—C14—C13−178.2 (5)N1—N2—B1—N6−61.5 (6)
B1—N4—C14—C13−5.0 (8)C7—N2—B1—N6115.1 (5)
C8—C9—C14—N4−0.8 (5)N5—N6—B1—N4−61.8 (5)
C10—C9—C14—N4179.7 (4)C21—N6—B1—N4107.6 (5)
C8—C9—C14—C13178.9 (4)N5—N6—B1—N264.5 (6)
C10—C9—C14—C13−0.6 (7)C21—N6—B1—N2−126.1 (5)
Acknowledgements top

We thank the Research Office of Azarbaijan University of Tarbiat Moallem, the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036) and the University of Malaya for supporting this study.

references
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