Abstract
The title compound, [Ag2(NCS)2(C14H38B10P2)2], was synthesized by the reaction of 1,2-bis(diisopropylphosphanyl)-1,2-dicarba-closo-dodecaborane with AgSCN. The diisopropylphosphanyl-closo-carborane ligand is coordinated in a bidentate manner to the AgI atom through the two P atoms. The coordination of the AgI atom is distorted tetrahedral, in which two vertices are formed by the P atoms of the chelating diphosphine ligand, and the other two are occupied by the S and N atoms of the two bridging thiocyanate anions, leading to a centrosymmetric binuclear complex. The distance between the two C atoms in the carborane skeleton is 1.851 (6) Å.
Related literature
For related structures, see: Zhang et al. (2006 ▶); Paavola et al. (2002 ▶, 2002a
▶,b
▶). For the synthesis and structure of 1,2-bis(diisopropylphosphanyl)-1,2-dicarba-closo-dodecaborane, see: Kivekäs et al. (1995 ▶).
Experimental
Crystal data
[Ag2(NCS)2(C14H38B10P2)2]
M r = 1084.87
Monoclinic,
a = 7.8075 (9) Å
b = 34.220 (3) Å
c = 10.6886 (12) Å
β = 110.074 (1)°
V = 2682.2 (5) Å3
Z = 2
Mo Kα radiation
μ = 0.95 mm−1
T = 298 K
0.41 × 0.18 × 0.08 mm
Data collection
Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.696, T max = 0.928
13386 measured reflections
4714 independent reflections
3238 reflections with I > 2σ(I)
R int = 0.050
Refinement
R[F 2 > 2σ(F 2)] = 0.052
wR(F 2) = 0.099
S = 1.06
4714 reflections
279 parameters
2 restraints
H-atom parameters constrained
Δρmax = 0.82 e Å−3
Δρmin = −0.92 e Å−3
Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049263/gk2319sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049263/gk2319Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Selected geometric parameters (Å, °).
| Ag1—N1 | 2.251 (5) |
| Ag1—P1 | 2.4566 (14) |
| Ag1—P2 | 2.4981 (14) |
| Ag1—S1 | 2.5693 (17) |
| P1—Ag1—P2 | 90.97 (4) |
| N1—Ag1—S1 | 97.27 (14) |
Acknowledgments
This work was supported by the National Natural Science Foundation of China (project No. 20971063), the Natural Science Foundation of Shandong Province (Y2007B01) and the Shandong Tai-Shan Scholar Research Fund.
supplementary crystallographic information
Comment
The synthesis and structure of 1,2-(PiPr2)2-1,2-C2B10H10 was reported by Kivekäs et al. (1995). Since then, only a few complexes of this ligand with Pt(II) and Pd(II) have been described (Paavola et al., 2002, 2002a,b). Here we report the structure of this ligand combined with Ag and thiocyanate ion.
As shown in Fig. 1, the coordination of the Ag atom is distorted tetrahedral, formed by one S atom and one N atom of the two SCN anions and the P atoms of diisopropylphosphanyl-closo-carborane ligand (Table 1). The two P—Ag bond lengths are slightly shorter than the corresponding bond lengths in the complex [Ag2Cl2(C26H30B10P2)2].2CH2Cl2 [2.5052 (14) Å; Zhang et al., 2006]). The P—Ag—P angle is slightly larger than the corresponding value of 89.80 Å for the complex [Ag2Cl2(C26H30B10P2)2].2CH2Cl2 (Zhang et al., 2006). The five-memebered chelate ring fomed by the silver atom, two phosphorus atoms and two carbon atoms of the carborane skeleton is strongly flattened with a maximum deviation of 0.322 Å for C2. The torsion angle P1—C1—C2—P2 is -0.4 (5)°, viz. smaller than that of 12.1 (2)° in the free ligand (Kivekäs et al., 1995).
Experimental
The title compound was synthesizd by the reaction of 1 mmol AgSCN and 1 mmol 1,2-(PiPr2)2-1,2-C2B10H10 in 10 ml dichloromethane under the protection of N2, refluxed for 4 h, then a colorless solution formed, and crystals suitable for X-ray diffraction were obtained from a dichloromethane- n-hexane solution.(61.7%, m.p. 553–558 K). FTIR (KBr) v (cm-l): 2989, 2966, 2930, 2872 (C—H); 2614, 2602, 2585, 2556 (B—H); 1071 (C—P).
Refinement
All H atoms were placed geometrically and treated as riding on their parent atoms, with B—H 1.10, C—H 0.96 (methyl), C—H 0.98 Å (isopropyl), with Uiso(H) = 1.2Ueq(B), Uiso(H) = 1.5Ueq(C). A rigid bond restraints were applied to the Uij values of Ag1,P1 and Ag1,P2 atoms via DELU instruction of SHELXL97 (Sheldrick, 2008).
Figures
Fig. 1.
The molecular structure of the title compound with atom labels and 40% probability displacement ellipsoids for non-H atoms. Symmetry code for atoms with the A label: -x + 1,-y,-z + 2. H atoms have been omitted for clarity.
Crystal data
| [Ag2(NCS)2(C14H38B10P2)2] | F(000) = 1112 |
| Mr = 1084.87 | Dx = 1.343 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3831 reflections |
| a = 7.8075 (9) Å | θ = 2.4–25.8° |
| b = 34.220 (3) Å | µ = 0.95 mm−1 |
| c = 10.6886 (12) Å | T = 298 K |
| β = 110.074 (1)° | Block, yellow |
| V = 2682.2 (5) Å3 | 0.41 × 0.18 × 0.08 mm |
| Z = 2 |
Data collection
| Bruker SMART 1000 CCD diffractometer | 4714 independent reflections |
| Radiation source: fine-focus sealed tube | 3238 reflections with I > 2σ(I) |
| graphite | Rint = 0.050 |
| φ and ω scans | θmax = 25.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
| Tmin = 0.696, Tmax = 0.928 | k = −36→40 |
| 13386 measured reflections | l = −12→10 |
Refinement
| 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.099 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0185P)2 + 6.4963P] where P = (Fo2 + 2Fc2)/3 |
| 4714 reflections | (Δ/σ)max = 0.001 |
| 279 parameters | Δρmax = 0.82 e Å−3 |
| 2 restraints | Δρmin = −0.92 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Ag1 | 0.61123 (6) | 0.074944 (11) | 0.96399 (4) | 0.04357 (15) | |
| P1 | 0.77035 (19) | 0.13609 (4) | 1.05474 (12) | 0.0319 (3) | |
| P2 | 0.62319 (19) | 0.09058 (4) | 0.73885 (13) | 0.0335 (3) | |
| S1 | 0.2929 (2) | 0.06561 (4) | 0.9800 (2) | 0.0638 (5) | |
| C2 | 0.7012 (7) | 0.14225 (13) | 0.7460 (4) | 0.0309 (12) | |
| N1 | 0.7232 (7) | 0.01564 (15) | 1.0410 (5) | 0.0634 (16) | |
| C1 | 0.7792 (7) | 0.16616 (13) | 0.9114 (5) | 0.0311 (12) | |
| C3 | 0.4009 (7) | 0.08761 (15) | 0.6024 (5) | 0.0443 (14) | |
| H3A | 0.4158 | 0.0956 | 0.5187 | 0.053* | |
| C9 | 1.0151 (7) | 0.13069 (15) | 1.1608 (5) | 0.0398 (13) | |
| H9A | 1.0841 | 0.1309 | 1.0995 | 0.048* | |
| B1 | 0.5741 (8) | 0.17712 (16) | 0.7899 (5) | 0.0327 (14) | |
| H1 | 0.4439 | 0.1695 | 0.8022 | 0.039* | |
| B2 | 0.9279 (8) | 0.15162 (17) | 0.8327 (6) | 0.0342 (14) | |
| H2 | 1.0248 | 0.1276 | 0.8725 | 0.041* | |
| C4 | 0.7877 (8) | 0.06395 (14) | 0.6774 (5) | 0.0423 (14) | |
| H4A | 0.9030 | 0.0783 | 0.7119 | 0.051* | |
| B3 | 0.9813 (9) | 0.19488 (18) | 0.7612 (6) | 0.0420 (16) | |
| H3 | 1.1164 | 0.1997 | 0.7530 | 0.050* | |
| B4 | 0.8264 (9) | 0.16041 (18) | 0.6591 (6) | 0.0401 (16) | |
| H4 | 0.8620 | 0.1431 | 0.5848 | 0.048* | |
| B5 | 0.7755 (9) | 0.21104 (18) | 0.6369 (6) | 0.0469 (18) | |
| H5 | 0.7765 | 0.2270 | 0.5478 | 0.056* | |
| C10 | 0.6616 (8) | 0.16743 (16) | 1.1476 (5) | 0.0459 (15) | |
| H10A | 0.7314 | 0.1917 | 1.1744 | 0.055* | |
| B6 | 0.6018 (9) | 0.17690 (17) | 0.6309 (6) | 0.0371 (15) | |
| H6 | 0.4882 | 0.1708 | 0.5381 | 0.044* | |
| B7 | 0.7247 (9) | 0.21373 (16) | 0.8895 (6) | 0.0379 (16) | |
| H7 | 0.6898 | 0.2313 | 0.9636 | 0.045* | |
| B8 | 0.9487 (9) | 0.19743 (16) | 0.9160 (6) | 0.0370 (15) | |
| H8 | 1.0633 | 0.2041 | 1.0077 | 0.044* | |
| B9 | 0.6147 (10) | 0.22145 (17) | 0.7165 (6) | 0.0440 (17) | |
| H9 | 0.5083 | 0.2439 | 0.6792 | 0.053* | |
| C11 | 0.4625 (8) | 0.17704 (17) | 1.0711 (6) | 0.0542 (16) | |
| H11A | 0.3993 | 0.1537 | 1.0310 | 0.081* | |
| H11B | 0.4556 | 0.1958 | 1.0029 | 0.081* | |
| H11C | 0.4072 | 0.1877 | 1.1312 | 0.081* | |
| C5 | 0.8260 (9) | 0.02295 (16) | 0.7408 (6) | 0.0586 (18) | |
| H5A | 0.7171 | 0.0074 | 0.7089 | 0.088* | |
| H5B | 0.8637 | 0.0253 | 0.8359 | 0.088* | |
| H5C | 0.9209 | 0.0106 | 0.7169 | 0.088* | |
| B10 | 0.8498 (9) | 0.23347 (17) | 0.7945 (6) | 0.0426 (17) | |
| H10 | 0.8978 | 0.2639 | 0.8068 | 0.051* | |
| C12 | 0.6691 (9) | 0.1440 (2) | 1.2724 (5) | 0.069 (2) | |
| H12A | 0.6220 | 0.1596 | 1.3277 | 0.104* | |
| H12B | 0.7932 | 0.1369 | 1.3213 | 0.104* | |
| H12C | 0.5968 | 0.1207 | 1.2460 | 0.104* | |
| C6 | 0.2489 (8) | 0.11169 (17) | 0.6243 (6) | 0.0529 (16) | |
| H6A | 0.1335 | 0.1040 | 0.5607 | 0.079* | |
| H6B | 0.2694 | 0.1389 | 0.6131 | 0.079* | |
| H6C | 0.2481 | 0.1073 | 0.7128 | 0.079* | |
| C7 | 0.3449 (9) | 0.04416 (17) | 0.5935 (6) | 0.0640 (19) | |
| H7A | 0.3260 | 0.0366 | 0.6742 | 0.096* | |
| H7B | 0.4397 | 0.0284 | 0.5813 | 0.096* | |
| H7C | 0.2340 | 0.0405 | 0.5193 | 0.096* | |
| C8 | 0.7401 (9) | 0.06209 (17) | 0.5261 (6) | 0.0611 (18) | |
| H8A | 0.8417 | 0.0517 | 0.5059 | 0.092* | |
| H8B | 0.7129 | 0.0879 | 0.4894 | 0.092* | |
| H8C | 0.6357 | 0.0455 | 0.4883 | 0.092* | |
| C13 | 1.0984 (8) | 0.16309 (17) | 1.2634 (5) | 0.0591 (18) | |
| H13A | 1.0457 | 0.1620 | 1.3324 | 0.089* | |
| H13B | 1.0736 | 0.1881 | 1.2202 | 0.089* | |
| H13C | 1.2278 | 0.1593 | 1.3018 | 0.089* | |
| C15 | 0.7150 (8) | −0.01747 (17) | 1.0327 (6) | 0.0467 (15) | |
| C14 | 1.0478 (8) | 0.09062 (17) | 1.2272 (6) | 0.0565 (17) | |
| H14A | 1.1762 | 0.0867 | 1.2715 | 0.085* | |
| H14B | 1.0012 | 0.0707 | 1.1608 | 0.085* | |
| H14C | 0.9864 | 0.0892 | 1.2910 | 0.085* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag1 | 0.0537 (3) | 0.0293 (2) | 0.0454 (2) | −0.0062 (2) | 0.0139 (2) | 0.0046 (2) |
| P1 | 0.0414 (9) | 0.0266 (7) | 0.0250 (7) | −0.0005 (6) | 0.0079 (6) | 0.0023 (5) |
| P2 | 0.0384 (9) | 0.0254 (7) | 0.0320 (6) | −0.0020 (6) | 0.0060 (6) | −0.0047 (6) |
| S1 | 0.0635 (12) | 0.0317 (9) | 0.1096 (14) | 0.0047 (7) | 0.0469 (11) | 0.0074 (8) |
| C2 | 0.040 (3) | 0.023 (3) | 0.025 (3) | 0.001 (2) | 0.005 (2) | 0.000 (2) |
| N1 | 0.051 (4) | 0.039 (3) | 0.093 (4) | 0.003 (3) | 0.015 (3) | 0.023 (3) |
| C1 | 0.035 (3) | 0.021 (3) | 0.032 (3) | −0.002 (2) | 0.005 (2) | 0.001 (2) |
| C3 | 0.044 (4) | 0.039 (3) | 0.042 (3) | −0.006 (3) | 0.005 (3) | −0.009 (3) |
| C9 | 0.039 (3) | 0.042 (3) | 0.032 (3) | −0.001 (3) | 0.004 (3) | 0.007 (2) |
| B1 | 0.037 (4) | 0.032 (3) | 0.025 (3) | 0.005 (3) | 0.006 (3) | 0.002 (2) |
| B2 | 0.038 (4) | 0.029 (3) | 0.034 (3) | 0.000 (3) | 0.011 (3) | −0.001 (3) |
| C4 | 0.050 (4) | 0.030 (3) | 0.045 (3) | −0.001 (3) | 0.014 (3) | −0.010 (2) |
| B3 | 0.049 (4) | 0.035 (4) | 0.045 (4) | 0.000 (3) | 0.021 (3) | 0.006 (3) |
| B4 | 0.047 (4) | 0.043 (4) | 0.030 (3) | 0.002 (3) | 0.012 (3) | 0.005 (3) |
| B5 | 0.057 (5) | 0.039 (4) | 0.043 (4) | −0.002 (3) | 0.015 (3) | 0.017 (3) |
| C10 | 0.060 (4) | 0.039 (3) | 0.036 (3) | −0.002 (3) | 0.014 (3) | −0.004 (3) |
| B6 | 0.046 (4) | 0.035 (3) | 0.027 (3) | 0.005 (3) | 0.008 (3) | 0.010 (3) |
| B7 | 0.054 (4) | 0.016 (3) | 0.034 (3) | 0.007 (3) | 0.003 (3) | −0.001 (2) |
| B8 | 0.043 (4) | 0.025 (3) | 0.039 (4) | −0.010 (3) | 0.009 (3) | 0.001 (3) |
| B9 | 0.056 (5) | 0.026 (3) | 0.044 (4) | 0.004 (3) | 0.011 (3) | 0.009 (3) |
| C11 | 0.064 (4) | 0.058 (4) | 0.047 (4) | 0.007 (3) | 0.028 (3) | −0.009 (3) |
| C5 | 0.064 (5) | 0.038 (4) | 0.069 (4) | 0.010 (3) | 0.017 (4) | −0.006 (3) |
| B10 | 0.056 (5) | 0.022 (3) | 0.050 (4) | −0.003 (3) | 0.019 (4) | 0.004 (3) |
| C12 | 0.088 (5) | 0.088 (5) | 0.034 (4) | 0.016 (4) | 0.025 (4) | 0.006 (3) |
| C6 | 0.039 (4) | 0.060 (4) | 0.053 (4) | −0.006 (3) | 0.006 (3) | −0.005 (3) |
| C7 | 0.056 (5) | 0.058 (4) | 0.066 (4) | −0.017 (3) | 0.006 (3) | −0.021 (3) |
| C8 | 0.081 (5) | 0.053 (4) | 0.056 (4) | −0.006 (3) | 0.032 (4) | −0.015 (3) |
| C13 | 0.057 (4) | 0.058 (4) | 0.045 (4) | −0.017 (3) | −0.005 (3) | 0.001 (3) |
| C15 | 0.039 (4) | 0.046 (4) | 0.058 (4) | 0.006 (3) | 0.020 (3) | 0.026 (3) |
| C14 | 0.059 (4) | 0.055 (4) | 0.044 (4) | 0.006 (3) | 0.004 (3) | 0.017 (3) |
Geometric parameters (Å, °)
| Ag1—N1 | 2.251 (5) | B4—H4 | 1.1000 |
| Ag1—P1 | 2.4566 (14) | B5—B10 | 1.759 (9) |
| Ag1—P2 | 2.4981 (14) | B5—B6 | 1.775 (9) |
| Ag1—S1 | 2.5693 (17) | B5—B9 | 1.778 (10) |
| P1—C10 | 1.853 (6) | B5—H5 | 1.1000 |
| P1—C1 | 1.866 (5) | C10—C11 | 1.524 (8) |
| P1—C9 | 1.867 (5) | C10—C12 | 1.541 (7) |
| P2—C3 | 1.847 (5) | C10—H10A | 0.9800 |
| P2—C2 | 1.863 (5) | B6—B9 | 1.763 (8) |
| P2—C4 | 1.868 (5) | B6—H6 | 1.1000 |
| S1—C15i | 1.652 (6) | B7—B8 | 1.763 (9) |
| C2—B4 | 1.682 (8) | B7—B10 | 1.767 (9) |
| C2—B6 | 1.693 (7) | B7—B9 | 1.771 (8) |
| C2—B1 | 1.717 (7) | B7—H7 | 1.1000 |
| C2—B2 | 1.723 (8) | B8—B10 | 1.765 (8) |
| C2—C1 | 1.851 (6) | B8—H8 | 1.1000 |
| N1—C15 | 1.137 (7) | B9—B10 | 1.784 (9) |
| C1—B7 | 1.678 (7) | B9—H9 | 1.1000 |
| C1—B8 | 1.689 (7) | C11—H11A | 0.9600 |
| C1—B1 | 1.722 (7) | C11—H11B | 0.9600 |
| C1—B2 | 1.725 (8) | C11—H11C | 0.9600 |
| C3—C6 | 1.527 (7) | C5—H5A | 0.9600 |
| C3—C7 | 1.543 (7) | C5—H5B | 0.9600 |
| C3—H3A | 0.9800 | C5—H5C | 0.9600 |
| C9—C14 | 1.525 (7) | B10—H10 | 1.1000 |
| C9—C13 | 1.538 (7) | C12—H12A | 0.9600 |
| C9—H9A | 0.9800 | C12—H12B | 0.9600 |
| B1—B6 | 1.786 (8) | C12—H12C | 0.9600 |
| B1—B9 | 1.786 (8) | C6—H6A | 0.9600 |
| B1—B7 | 1.796 (8) | C6—H6B | 0.9600 |
| B1—H1 | 1.1000 | C6—H6C | 0.9600 |
| B2—B4 | 1.775 (8) | C7—H7A | 0.9600 |
| B2—B3 | 1.780 (8) | C7—H7B | 0.9600 |
| B2—B8 | 1.783 (8) | C7—H7C | 0.9600 |
| B2—H2 | 1.1000 | C8—H8A | 0.9600 |
| C4—C8 | 1.531 (7) | C8—H8B | 0.9600 |
| C4—C5 | 1.542 (7) | C8—H8C | 0.9600 |
| C4—H4A | 0.9800 | C13—H13A | 0.9600 |
| B3—B8 | 1.761 (9) | C13—H13B | 0.9600 |
| B3—B4 | 1.772 (9) | C13—H13C | 0.9600 |
| B3—B10 | 1.782 (9) | C15—S1i | 1.652 (6) |
| B3—B5 | 1.785 (9) | C14—H14A | 0.9600 |
| B3—H3 | 1.1000 | C14—H14B | 0.9600 |
| B4—B6 | 1.767 (9) | C14—H14C | 0.9600 |
| B4—B5 | 1.775 (9) | ||
| N1—Ag1—P1 | 122.90 (14) | B9—B5—B3 | 108.0 (4) |
| N1—Ag1—P2 | 114.03 (15) | B10—B5—H5 | 121.0 |
| P1—Ag1—P2 | 90.97 (4) | B4—B5—H5 | 122.2 |
| N1—Ag1—S1 | 97.27 (14) | B6—B5—H5 | 121.9 |
| P1—Ag1—S1 | 116.70 (5) | B9—B5—H5 | 122.0 |
| P2—Ag1—S1 | 116.60 (6) | B3—B5—H5 | 121.8 |
| C10—P1—C1 | 105.9 (2) | C11—C10—C12 | 107.8 (5) |
| C10—P1—C9 | 107.1 (3) | C11—C10—P1 | 114.1 (4) |
| C1—P1—C9 | 103.6 (2) | C12—C10—P1 | 105.9 (4) |
| C10—P1—Ag1 | 116.2 (2) | C11—C10—H10A | 109.6 |
| C1—P1—Ag1 | 107.57 (15) | C12—C10—H10A | 109.6 |
| C9—P1—Ag1 | 115.41 (17) | P1—C10—H10A | 109.6 |
| C3—P2—C2 | 106.9 (2) | C2—B6—B9 | 107.3 (4) |
| C3—P2—C4 | 105.6 (2) | C2—B6—B4 | 58.1 (3) |
| C2—P2—C4 | 102.9 (2) | B9—B6—B4 | 108.1 (5) |
| C3—P2—Ag1 | 114.4 (2) | C2—B6—B5 | 106.3 (4) |
| C2—P2—Ag1 | 106.46 (15) | B9—B6—B5 | 60.4 (4) |
| C4—P2—Ag1 | 119.45 (17) | B4—B6—B5 | 60.2 (4) |
| C15i—S1—Ag1 | 97.4 (2) | C2—B6—B1 | 59.1 (3) |
| B4—C2—B6 | 63.1 (3) | B9—B6—B1 | 60.4 (3) |
| B4—C2—B1 | 113.2 (4) | B4—B6—B1 | 106.0 (4) |
| B6—C2—B1 | 63.1 (3) | B5—B6—B1 | 107.7 (4) |
| B4—C2—B2 | 62.9 (3) | C2—B6—H6 | 123.3 |
| B6—C2—B2 | 113.0 (4) | B9—B6—H6 | 121.1 |
| B1—C2—B2 | 107.9 (4) | B4—B6—H6 | 122.6 |
| B4—C2—C1 | 107.6 (4) | B5—B6—H6 | 121.8 |
| B6—C2—C1 | 107.6 (3) | B1—B6—H6 | 122.4 |
| B1—C2—C1 | 57.6 (3) | C1—B7—B8 | 58.7 (3) |
| B2—C2—C1 | 57.6 (3) | C1—B7—B10 | 106.7 (4) |
| B4—C2—P2 | 124.9 (4) | B8—B7—B10 | 60.0 (4) |
| B6—C2—P2 | 124.9 (3) | C1—B7—B9 | 107.4 (4) |
| B1—C2—P2 | 117.3 (4) | B8—B7—B9 | 108.3 (5) |
| B2—C2—P2 | 117.4 (3) | B10—B7—B9 | 60.5 (4) |
| C1—C2—P2 | 117.0 (3) | C1—B7—B1 | 59.3 (3) |
| C15—N1—Ag1 | 150.0 (5) | B8—B7—B1 | 106.6 (4) |
| B7—C1—B8 | 63.2 (3) | B10—B7—B1 | 107.7 (4) |
| B7—C1—B1 | 63.8 (3) | B9—B7—B1 | 60.1 (3) |
| B8—C1—B1 | 113.6 (4) | C1—B7—H7 | 122.9 |
| B7—C1—B2 | 113.1 (4) | B8—B7—H7 | 122.3 |
| B8—C1—B2 | 62.9 (3) | B10—B7—H7 | 121.8 |
| B1—C1—B2 | 107.6 (4) | B9—B7—H7 | 121.2 |
| B7—C1—C2 | 108.1 (3) | B1—B7—H7 | 122.3 |
| B8—C1—C2 | 107.8 (4) | C1—B8—B7 | 58.1 (3) |
| B1—C1—C2 | 57.3 (3) | C1—B8—B3 | 107.8 (4) |
| B2—C1—C2 | 57.5 (3) | B7—B8—B3 | 108.7 (4) |
| B7—C1—P1 | 124.8 (4) | C1—B8—B10 | 106.3 (4) |
| B8—C1—P1 | 125.1 (3) | B7—B8—B10 | 60.1 (4) |
| B1—C1—P1 | 116.9 (3) | B3—B8—B10 | 60.7 (3) |
| B2—C1—P1 | 117.5 (3) | C1—B8—B2 | 59.5 (3) |
| C2—C1—P1 | 116.6 (3) | B7—B8—B2 | 106.4 (4) |
| C6—C3—C7 | 108.1 (5) | B3—B8—B2 | 60.3 (3) |
| C6—C3—P2 | 114.7 (4) | B10—B8—B2 | 107.7 (4) |
| C7—C3—P2 | 105.8 (4) | C1—B8—H8 | 123.1 |
| C6—C3—H3A | 109.4 | B7—B8—H8 | 122.4 |
| C7—C3—H3A | 109.4 | B3—B8—H8 | 120.8 |
| P2—C3—H3A | 109.4 | B10—B8—H8 | 121.9 |
| C14—C9—C13 | 110.7 (4) | B2—B8—H8 | 122.2 |
| C14—C9—P1 | 110.1 (4) | B6—B9—B7 | 109.5 (4) |
| C13—C9—P1 | 117.1 (4) | B6—B9—B5 | 60.1 (4) |
| C14—C9—H9A | 106.0 | B7—B9—B5 | 107.5 (5) |
| C13—C9—H9A | 106.0 | B6—B9—B10 | 108.0 (5) |
| P1—C9—H9A | 106.0 | B7—B9—B10 | 59.6 (4) |
| C2—B1—C1 | 65.1 (3) | B5—B9—B10 | 59.2 (4) |
| C2—B1—B6 | 57.8 (3) | B6—B9—B1 | 60.4 (3) |
| C1—B1—B6 | 109.4 (4) | B7—B9—B1 | 60.7 (3) |
| C2—B1—B9 | 105.3 (4) | B5—B9—B1 | 107.5 (4) |
| C1—B1—B9 | 104.9 (4) | B10—B9—B1 | 107.5 (4) |
| B6—B1—B9 | 59.2 (3) | B6—B9—H9 | 120.9 |
| C2—B1—B7 | 108.9 (4) | B7—B9—H9 | 121.2 |
| C1—B1—B7 | 56.9 (3) | B5—B9—H9 | 122.4 |
| B6—B1—B7 | 107.4 (4) | B10—B9—H9 | 122.4 |
| B9—B1—B7 | 59.3 (3) | B1—B9—H9 | 121.7 |
| C2—B1—H1 | 120.8 | C10—C11—H11A | 109.5 |
| C1—B1—H1 | 121.1 | C10—C11—H11B | 109.5 |
| B6—B1—H1 | 122.1 | H11A—C11—H11B | 109.5 |
| B9—B1—H1 | 124.3 | C10—C11—H11C | 109.5 |
| B7—B1—H1 | 122.6 | H11A—C11—H11C | 109.5 |
| C2—B2—C1 | 65.0 (3) | H11B—C11—H11C | 109.5 |
| C2—B2—B4 | 57.4 (3) | C4—C5—H5A | 109.5 |
| C1—B2—B4 | 109.1 (4) | C4—C5—H5B | 109.5 |
| C2—B2—B3 | 105.8 (4) | H5A—C5—H5B | 109.5 |
| C1—B2—B3 | 105.4 (4) | C4—C5—H5C | 109.5 |
| B4—B2—B3 | 59.8 (3) | H5A—C5—H5C | 109.5 |
| C2—B2—B8 | 109.4 (4) | H5B—C5—H5C | 109.5 |
| C1—B2—B8 | 57.6 (3) | B8—B10—B5 | 108.5 (4) |
| B4—B2—B8 | 107.7 (4) | B8—B10—B7 | 59.9 (3) |
| B3—B2—B8 | 59.2 (3) | B5—B10—B7 | 108.6 (4) |
| C2—B2—H2 | 120.8 | B8—B10—B3 | 59.5 (3) |
| C1—B2—H2 | 121.1 | B5—B10—B3 | 60.5 (4) |
| B4—B2—H2 | 122.1 | B7—B10—B3 | 107.5 (4) |
| B3—B2—H2 | 123.9 | B8—B10—B9 | 107.6 (4) |
| B8—B2—H2 | 122.2 | B5—B10—B9 | 60.3 (4) |
| C8—C4—C5 | 111.5 (4) | B7—B10—B9 | 59.8 (3) |
| C8—C4—P2 | 116.4 (4) | B3—B10—B9 | 107.9 (4) |
| C5—C4—P2 | 110.0 (4) | B8—B10—H10 | 121.9 |
| C8—C4—H4A | 106.1 | B5—B10—H10 | 121.0 |
| C5—C4—H4A | 106.1 | B7—B10—H10 | 121.8 |
| P2—C4—H4A | 106.1 | B3—B10—H10 | 122.0 |
| B8—B3—B4 | 108.9 (4) | B9—B10—H10 | 121.9 |
| B8—B3—B2 | 60.5 (3) | C10—C12—H12A | 109.5 |
| B4—B3—B2 | 60.0 (3) | C10—C12—H12B | 109.5 |
| B8—B3—B10 | 59.8 (3) | H12A—C12—H12B | 109.5 |
| B4—B3—B10 | 107.3 (5) | C10—C12—H12C | 109.5 |
| B2—B3—B10 | 107.1 (4) | H12A—C12—H12C | 109.5 |
| B8—B3—B5 | 107.5 (5) | H12B—C12—H12C | 109.5 |
| B4—B3—B5 | 59.9 (4) | C3—C6—H6A | 109.5 |
| B2—B3—B5 | 107.1 (5) | C3—C6—H6B | 109.5 |
| B10—B3—B5 | 59.1 (4) | H6A—C6—H6B | 109.5 |
| B8—B3—H3 | 121.2 | C3—C6—H6C | 109.5 |
| B4—B3—H3 | 121.4 | H6A—C6—H6C | 109.5 |
| B2—B3—H3 | 122.1 | H6B—C6—H6C | 109.5 |
| B10—B3—H3 | 122.6 | C3—C7—H7A | 109.5 |
| B5—B3—H3 | 122.5 | C3—C7—H7B | 109.5 |
| C2—B4—B6 | 58.8 (3) | H7A—C7—H7B | 109.5 |
| C2—B4—B3 | 108.0 (4) | C3—C7—H7C | 109.5 |
| B6—B4—B3 | 108.7 (5) | H7A—C7—H7C | 109.5 |
| C2—B4—B5 | 106.8 (4) | H7B—C7—H7C | 109.5 |
| B6—B4—B5 | 60.1 (4) | C4—C8—H8A | 109.5 |
| B3—B4—B5 | 60.4 (4) | C4—C8—H8B | 109.5 |
| C2—B4—B2 | 59.7 (3) | H8A—C8—H8B | 109.5 |
| B6—B4—B2 | 107.1 (4) | C4—C8—H8C | 109.5 |
| B3—B4—B2 | 60.2 (3) | H8A—C8—H8C | 109.5 |
| B5—B4—B2 | 107.7 (4) | H8B—C8—H8C | 109.5 |
| C2—B4—H4 | 122.6 | C9—C13—H13A | 109.5 |
| B6—B4—H4 | 122.0 | C9—C13—H13B | 109.5 |
| B3—B4—H4 | 121.0 | H13A—C13—H13B | 109.5 |
| B5—B4—H4 | 121.9 | C9—C13—H13C | 109.5 |
| B2—B4—H4 | 122.1 | H13A—C13—H13C | 109.5 |
| B10—B5—B4 | 108.2 (4) | H13B—C13—H13C | 109.5 |
| B10—B5—B6 | 108.6 (5) | N1—C15—S1i | 178.8 (6) |
| B4—B5—B6 | 59.7 (3) | C9—C14—H14A | 109.5 |
| B10—B5—B9 | 60.6 (4) | C9—C14—H14B | 109.5 |
| B4—B5—B9 | 107.1 (4) | H14A—C14—H14B | 109.5 |
| B6—B5—B9 | 59.5 (4) | C9—C14—H14C | 109.5 |
| B10—B5—B3 | 60.4 (4) | H14A—C14—H14C | 109.5 |
| B4—B5—B3 | 59.7 (3) | H14B—C14—H14C | 109.5 |
| B6—B5—B3 | 107.7 (4) | ||
| N1—Ag1—P1—C10 | −111.6 (3) | Ag1—P2—C2—C1 | 8.3 (3) |
| P2—Ag1—P1—C10 | 128.6 (2) | P1—Ag1—N1—C15 | −172.8 (9) |
| S1—Ag1—P1—C10 | 8.0 (2) | P2—Ag1—N1—C15 | −64.7 (10) |
| N1—Ag1—P1—C1 | 130.0 (2) | S1—Ag1—N1—C15 | 58.7 (10) |
| P2—Ag1—P1—C1 | 10.24 (17) | P2—C2—C1—P1 | −0.4 (5) |
| S1—Ag1—P1—C1 | −110.41 (18) | C10—P1—C1—C2 | −132.8 (3) |
| N1—Ag1—P1—C9 | 15.0 (3) | C9—P1—C1—C2 | 114.7 (3) |
| P2—Ag1—P1—C9 | −104.8 (2) | Ag1—P1—C1—C2 | −7.9 (4) |
| S1—Ag1—P1—C9 | 134.6 (2) | C2—P2—C3—C6 | −64.1 (5) |
| N1—Ag1—P2—C3 | 104.8 (2) | C4—P2—C3—C6 | −173.2 (4) |
| P1—Ag1—P2—C3 | −128.15 (19) | Ag1—P2—C3—C6 | 53.4 (5) |
| S1—Ag1—P2—C3 | −7.42 (19) | C2—P2—C3—C7 | 176.9 (4) |
| N1—Ag1—P2—C2 | −137.4 (2) | C4—P2—C3—C7 | 67.8 (4) |
| P1—Ag1—P2—C2 | −10.35 (17) | Ag1—P2—C3—C7 | −65.6 (4) |
| S1—Ag1—P2—C2 | 110.38 (17) | C10—P1—C9—C14 | 103.2 (4) |
| N1—Ag1—P2—C4 | −21.7 (3) | C1—P1—C9—C14 | −145.2 (4) |
| P1—Ag1—P2—C4 | 105.3 (2) | Ag1—P1—C9—C14 | −28.0 (4) |
| S1—Ag1—P2—C4 | −133.9 (2) | C10—P1—C9—C13 | −24.5 (5) |
| C3—P2—C2—B4 | −88.9 (4) | C1—P1—C9—C13 | 87.1 (4) |
| C4—P2—C2—B4 | 22.0 (5) | Ag1—P1—C9—C13 | −155.7 (4) |
| Ag1—P2—C2—B4 | 148.4 (4) | C3—P2—C4—C8 | 25.7 (5) |
| C3—P2—C2—B6 | −9.6 (5) | C2—P2—C4—C8 | −86.2 (4) |
| C4—P2—C2—B6 | 101.4 (4) | Ag1—P2—C4—C8 | 156.3 (3) |
| Ag1—P2—C2—B6 | −132.2 (4) | C3—P2—C4—C5 | −102.3 (4) |
| C3—P2—C2—B1 | 65.4 (4) | C2—P2—C4—C5 | 145.8 (4) |
| C4—P2—C2—B1 | 176.3 (3) | Ag1—P2—C4—C5 | 28.3 (4) |
| Ag1—P2—C2—B1 | −57.3 (3) | C1—P1—C10—C11 | 66.3 (5) |
| C3—P2—C2—B2 | −163.5 (4) | C9—P1—C10—C11 | 176.3 (4) |
| C4—P2—C2—B2 | −52.6 (4) | Ag1—P1—C10—C11 | −53.0 (4) |
| Ag1—P2—C2—B2 | 73.8 (4) | C1—P1—C10—C12 | −175.3 (4) |
| C3—P2—C2—C1 | 130.9 (3) | C9—P1—C10—C12 | −65.3 (4) |
| C4—P2—C2—C1 | −118.1 (3) | Ag1—P1—C10—C12 | 65.4 (4) |
Symmetry codes: (i) −x+1, −y, −z+2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2319).
References
- Kivekäs, R., Sillanpää, R., Teixidor, F., Viñas, C., Nuñez, R. & Abad, M. (1995). Acta Cryst. C51, 1864–1868.
- Paavola, S., Kivekäs, R., Teixidor, F. & Vinas, C. (2002). J. Organomet. Chem. 606, 183–187.
- Paavola, S., Teixidor, F., Viñas, C. & Kivekäs, R. (2002a). Acta Cryst. C58, m237–m239. [DOI] [PubMed]
- Paavola, S., Teixidor, F., Vinas, C. & Kivekas, R. (2002b). J. Organomet. Chem. 645, 39–46.
- Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
- Zhang, D.-P., Dou, J.-M., Li, D.-C. & Wang, D.-Q. (2006). Acta Cryst. E62, o418–o419.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049263/gk2319sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049263/gk2319Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

