metal-organic compounds
[Bis[μ-bis(diphenylphosphino)methane-1:2κ2P:P′]-bis(nitrito-κ2O,O′)]disilver(I) acetonitrile disolvate
aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and bKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
*Correspondence e-mail: jinqh204@163.com
The title complex, [Ag2(NO2)2(C25H22P2)2]·2CH3CN, is a centrosymmetric dimer in which two bis(diphenylphosphino)methane ligands bridge two Ag+ ions, forming an eight-membered ring with a short Ag⋯Ag separation of 3.1809 (5) Å. The distorted P2O2 coordination of the cation is completed by two O-donors from a symmetric bidentate chelate NO2− anion [Ag—O = 2.550 (3) and 2.567 (3) Å].
Related literature
The coordination chemistry of silver(I) complexes has been extensively studied, see: Bowmaker et al. (1993); Cui, Hu et al. (2010); Cui, Jin et al. (2010); Jin, Hu et al. (2010); Jin, Song et al. (2010); Meijboom et al. (2009). For related structures, see: Effendy et al. (2004); Jin et al. (2008); Ma et al. (2009); Song et al. (2010).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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.
Supporting information
10.1107/S1600536812041931/zs2232sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041931/zs2232Isup2.hkl
The title complex was synthesized using the following procedure. Bis(diphenylphosphino)methane (dppm, 0.0769 g, 0.2 mmol) was added to a stirred solution of AgNO2 (0.0308 g, 0.2 mmol) and 1,2-bis(4-pyridyl)ethane (0.0368 g, 0.2 mmol) in a mixture of CH3CN (5 ml) and H2O (5 ml). Stirring was continued for 6 h at room temperature, after which the white precipitate was filtered off. Subsequent slow evaporation of the colorless filtrate at ambient temperature resulted in the formation of colorless crystals of the title complex. Crystals suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.
The final refinements were performed with isotropic thermal parameters. All hydrogen atoms were located in calculated sites with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) or 0.97 Å (methylene) and included in the
in the riding model approximation with Uiso(H) = 1.2Ueq(aromatic and methylene C) or 1.5Ueq(methyl C).Data collection: SMART (Bruker, 2007); cell
SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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 (Sheldrick, 2008).Fig. 1. The molecular [Ag2(C25H22P2)2(NO2)2].2(CH3CN), showing the atom-numbering scheme, with displacement ellipsoids drawn at the 30% probability level. For symmetry code (i): -x+1, -y+1, -z+1. |
[Ag2(NO2)2(C25H22P2)2]·2C2H3N | F(000) = 1176 |
Mr = 1158.60 | Dx = 1.429 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6670 reflections |
a = 12.1390 (11) Å | θ = 2.5–28.2° |
b = 11.1247 (9) Å | µ = 0.89 mm−1 |
c = 20.0350 (18) Å | T = 298 K |
β = 95.543 (1)° | Block, colourless |
V = 2692.9 (4) Å3 | 0.40 × 0.35 × 0.33 mm |
Z = 2 |
Bruker SMART CCD area detector diffractometer | 4752 independent reflections |
Radiation source: fine-focus sealed tube | 3845 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −14→13 |
Tmin = 0.717, Tmax = 0.757 | k = −13→13 |
13205 measured reflections | l = −23→18 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.037P)2 + 2.4337P] where P = (Fo2 + 2Fc2)/3 |
4752 reflections | (Δ/σ)max = 0.002 |
308 parameters | Δρmax = 1.01 e Å−3 |
3 restraints | Δρmin = −0.46 e Å−3 |
[Ag2(NO2)2(C25H22P2)2]·2C2H3N | V = 2692.9 (4) Å3 |
Mr = 1158.60 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.1390 (11) Å | µ = 0.89 mm−1 |
b = 11.1247 (9) Å | T = 298 K |
c = 20.0350 (18) Å | 0.40 × 0.35 × 0.33 mm |
β = 95.543 (1)° |
Bruker SMART CCD area detector diffractometer | 4752 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 3845 reflections with I > 2σ(I) |
Tmin = 0.717, Tmax = 0.757 | Rint = 0.035 |
13205 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 3 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.01 e Å−3 |
4752 reflections | Δρmin = −0.46 e Å−3 |
308 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 | ||
Ag1 | 0.43541 (2) | 0.61579 (2) | 0.521730 (12) | 0.03586 (10) | |
P1 | 0.55178 (7) | 0.70130 (8) | 0.43866 (4) | 0.0324 (2) | |
P2 | 0.43562 (7) | 0.53526 (8) | 0.63500 (4) | 0.0327 (2) | |
N1 | 0.2195 (3) | 0.6845 (4) | 0.44450 (19) | 0.0626 (10) | |
N2 | 0.9358 (7) | 0.8704 (8) | 0.6794 (5) | 0.154 (3) | |
O1 | 0.2546 (3) | 0.7319 (3) | 0.49890 (16) | 0.0729 (9) | |
O2 | 0.2823 (2) | 0.6093 (3) | 0.42403 (16) | 0.0627 (7) | |
C1 | 0.5182 (3) | 0.6221 (3) | 0.35872 (17) | 0.0369 (8) | |
H1A | 0.5540 | 0.6623 | 0.3236 | 0.044* | |
H1B | 0.4389 | 0.6247 | 0.3467 | 0.044* | |
C2 | 0.5182 (3) | 0.8565 (3) | 0.41655 (17) | 0.0373 (8) | |
C3 | 0.4172 (3) | 0.8834 (3) | 0.3812 (2) | 0.0498 (10) | |
H3 | 0.3691 | 0.8215 | 0.3669 | 0.060* | |
C4 | 0.3871 (4) | 1.0011 (4) | 0.3668 (2) | 0.0649 (12) | |
H4 | 0.3198 | 1.0177 | 0.3424 | 0.078* | |
C5 | 0.4561 (5) | 1.0931 (4) | 0.3883 (2) | 0.0682 (14) | |
H5 | 0.4352 | 1.1722 | 0.3791 | 0.082* | |
C6 | 0.5555 (4) | 1.0693 (4) | 0.4234 (2) | 0.0619 (12) | |
H6 | 0.6021 | 1.1322 | 0.4381 | 0.074* | |
C7 | 0.5875 (3) | 0.9515 (3) | 0.43718 (19) | 0.0485 (9) | |
H7 | 0.6561 | 0.9359 | 0.4605 | 0.058* | |
C8 | 0.7019 (3) | 0.6971 (3) | 0.45118 (18) | 0.0412 (8) | |
C9 | 0.7677 (3) | 0.7389 (4) | 0.4033 (2) | 0.0649 (12) | |
H9 | 0.7354 | 0.7722 | 0.3635 | 0.078* | |
C10 | 0.8810 (4) | 0.7309 (6) | 0.4150 (3) | 0.0925 (18) | |
H10 | 0.9250 | 0.7602 | 0.3831 | 0.111* | |
C11 | 0.9295 (4) | 0.6809 (6) | 0.4720 (4) | 0.110 (2) | |
H11 | 1.0063 | 0.6755 | 0.4788 | 0.131* | |
C12 | 0.8664 (5) | 0.6385 (6) | 0.5193 (4) | 0.108 (2) | |
H12 | 0.8997 | 0.6032 | 0.5582 | 0.129* | |
C13 | 0.7513 (4) | 0.6482 (4) | 0.5093 (2) | 0.0674 (13) | |
H13 | 0.7081 | 0.6214 | 0.5421 | 0.081* | |
C14 | 0.5351 (3) | 0.6152 (3) | 0.69330 (16) | 0.0374 (8) | |
C15 | 0.5009 (4) | 0.7003 (4) | 0.73770 (18) | 0.0523 (10) | |
H15 | 0.4260 | 0.7099 | 0.7425 | 0.063* | |
C16 | 0.5793 (4) | 0.7712 (4) | 0.7751 (2) | 0.0650 (12) | |
H16 | 0.5563 | 0.8270 | 0.8054 | 0.078* | |
C17 | 0.6881 (4) | 0.7596 (4) | 0.7676 (2) | 0.0667 (13) | |
H17 | 0.7393 | 0.8089 | 0.7919 | 0.080* | |
C18 | 0.7238 (4) | 0.6755 (4) | 0.7245 (2) | 0.0620 (11) | |
H18 | 0.7990 | 0.6668 | 0.7202 | 0.074* | |
C19 | 0.6475 (3) | 0.6034 (3) | 0.6872 (2) | 0.0479 (9) | |
H19 | 0.6719 | 0.5467 | 0.6579 | 0.057* | |
C20 | 0.3075 (3) | 0.5396 (3) | 0.67562 (18) | 0.0447 (9) | |
C21 | 0.2194 (4) | 0.6045 (4) | 0.6469 (2) | 0.0674 (13) | |
H21 | 0.2235 | 0.6428 | 0.6060 | 0.081* | |
C22 | 0.1227 (4) | 0.6127 (6) | 0.6800 (3) | 0.101 (2) | |
H22 | 0.0635 | 0.6591 | 0.6618 | 0.121* | |
C23 | 0.1159 (5) | 0.5525 (7) | 0.7387 (3) | 0.097 (2) | |
H23 | 0.0509 | 0.5561 | 0.7596 | 0.117* | |
C24 | 0.2022 (5) | 0.4879 (6) | 0.7670 (3) | 0.0867 (17) | |
H24 | 0.1966 | 0.4478 | 0.8072 | 0.104* | |
C25 | 0.2989 (4) | 0.4813 (4) | 0.7361 (2) | 0.0630 (12) | |
H25 | 0.3586 | 0.4376 | 0.7559 | 0.076* | |
C26 | 0.9176 (7) | 0.9290 (8) | 0.6327 (6) | 0.124 (3) | |
C27 | 0.8934 (8) | 1.0016 (10) | 0.5727 (5) | 0.182 (4) | |
H27A | 0.8406 | 0.9604 | 0.5420 | 0.273* | |
H27B | 0.9603 | 1.0147 | 0.5517 | 0.273* | |
H27C | 0.8633 | 1.0775 | 0.5846 | 0.273* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.04039 (16) | 0.03674 (17) | 0.03093 (15) | 0.00023 (11) | 0.00592 (11) | 0.00355 (11) |
P1 | 0.0365 (5) | 0.0316 (5) | 0.0294 (4) | −0.0030 (4) | 0.0052 (4) | 0.0017 (4) |
P2 | 0.0383 (5) | 0.0328 (5) | 0.0274 (4) | −0.0006 (4) | 0.0060 (4) | 0.0002 (4) |
N1 | 0.045 (2) | 0.081 (3) | 0.060 (2) | 0.0081 (19) | −0.0008 (17) | 0.015 (2) |
N2 | 0.131 (6) | 0.147 (7) | 0.176 (8) | 0.016 (5) | −0.029 (6) | −0.015 (6) |
O1 | 0.0686 (18) | 0.088 (2) | 0.0610 (19) | 0.0234 (16) | 0.0020 (16) | −0.0021 (15) |
O2 | 0.0537 (17) | 0.069 (2) | 0.0640 (18) | 0.0051 (15) | −0.0012 (12) | −0.0018 (13) |
C1 | 0.0462 (19) | 0.0323 (18) | 0.0326 (18) | −0.0010 (15) | 0.0057 (15) | 0.0028 (14) |
C2 | 0.051 (2) | 0.0306 (18) | 0.0323 (18) | −0.0031 (15) | 0.0126 (16) | 0.0013 (14) |
C3 | 0.058 (2) | 0.035 (2) | 0.056 (2) | −0.0002 (18) | 0.0018 (19) | 0.0038 (17) |
C4 | 0.080 (3) | 0.050 (3) | 0.065 (3) | 0.014 (2) | 0.008 (2) | 0.015 (2) |
C5 | 0.111 (4) | 0.039 (2) | 0.060 (3) | 0.009 (3) | 0.034 (3) | 0.013 (2) |
C6 | 0.096 (4) | 0.033 (2) | 0.061 (3) | −0.015 (2) | 0.031 (3) | −0.009 (2) |
C7 | 0.061 (2) | 0.044 (2) | 0.043 (2) | −0.0107 (19) | 0.0157 (18) | −0.0063 (17) |
C8 | 0.0367 (18) | 0.040 (2) | 0.047 (2) | −0.0064 (15) | 0.0066 (16) | −0.0043 (17) |
C9 | 0.051 (2) | 0.087 (3) | 0.059 (3) | −0.016 (2) | 0.020 (2) | −0.007 (2) |
C10 | 0.057 (3) | 0.115 (5) | 0.112 (5) | −0.020 (3) | 0.039 (3) | −0.021 (4) |
C11 | 0.034 (3) | 0.118 (5) | 0.176 (7) | −0.006 (3) | 0.009 (4) | −0.010 (5) |
C12 | 0.053 (3) | 0.124 (5) | 0.139 (6) | 0.000 (3) | −0.029 (4) | 0.038 (4) |
C13 | 0.049 (2) | 0.075 (3) | 0.076 (3) | −0.004 (2) | −0.005 (2) | 0.021 (3) |
C14 | 0.050 (2) | 0.0329 (18) | 0.0287 (17) | −0.0038 (15) | 0.0016 (15) | 0.0020 (14) |
C15 | 0.067 (3) | 0.052 (2) | 0.040 (2) | −0.004 (2) | 0.0121 (19) | −0.0085 (18) |
C16 | 0.096 (4) | 0.055 (3) | 0.043 (2) | −0.011 (3) | 0.006 (2) | −0.017 (2) |
C17 | 0.082 (3) | 0.058 (3) | 0.055 (3) | −0.017 (2) | −0.021 (2) | −0.006 (2) |
C18 | 0.054 (2) | 0.065 (3) | 0.064 (3) | −0.006 (2) | −0.011 (2) | 0.000 (2) |
C19 | 0.048 (2) | 0.046 (2) | 0.048 (2) | 0.0000 (17) | −0.0022 (18) | −0.0030 (18) |
C20 | 0.048 (2) | 0.050 (2) | 0.039 (2) | −0.0062 (18) | 0.0155 (17) | −0.0082 (17) |
C21 | 0.051 (2) | 0.095 (4) | 0.057 (3) | 0.011 (2) | 0.014 (2) | 0.001 (3) |
C22 | 0.050 (3) | 0.152 (6) | 0.104 (5) | 0.020 (3) | 0.023 (3) | −0.006 (4) |
C23 | 0.073 (4) | 0.136 (6) | 0.090 (4) | −0.018 (4) | 0.049 (3) | −0.028 (4) |
C24 | 0.091 (4) | 0.106 (4) | 0.071 (3) | −0.021 (4) | 0.049 (3) | −0.008 (3) |
C25 | 0.070 (3) | 0.072 (3) | 0.051 (3) | −0.008 (2) | 0.024 (2) | 0.006 (2) |
C26 | 0.106 (6) | 0.106 (6) | 0.158 (9) | 0.002 (5) | −0.001 (6) | −0.026 (6) |
C27 | 0.182 (9) | 0.176 (10) | 0.190 (10) | −0.011 (8) | 0.035 (8) | 0.040 (9) |
Ag1—P2 | 2.4396 (9) | C10—H10 | 0.9300 |
Ag1—P1 | 2.4747 (9) | C11—C12 | 1.360 (9) |
Ag1—O1 | 2.550 (3) | C11—H11 | 0.9300 |
Ag1—O2 | 2.567 (3) | C12—C13 | 1.396 (7) |
Ag1—Ag1i | 3.1809 (5) | C12—H12 | 0.9300 |
P1—C8 | 1.816 (3) | C13—H13 | 0.9300 |
P1—C2 | 1.819 (3) | C14—C19 | 1.388 (5) |
P1—C1 | 1.839 (3) | C14—C15 | 1.390 (5) |
P2—C20 | 1.824 (4) | C15—C16 | 1.397 (6) |
P2—C14 | 1.827 (3) | C15—H15 | 0.9300 |
P2—C1i | 1.839 (3) | C16—C17 | 1.350 (6) |
N1—O2 | 1.229 (4) | C16—H16 | 0.9300 |
N1—O1 | 1.248 (5) | C17—C18 | 1.372 (6) |
N2—C26 | 1.144 (11) | C17—H17 | 0.9300 |
C1—P2i | 1.839 (3) | C18—C19 | 1.387 (6) |
C1—H1A | 0.9700 | C18—H18 | 0.9300 |
C1—H1B | 0.9700 | C19—H19 | 0.9300 |
C2—C3 | 1.388 (5) | C20—C21 | 1.371 (6) |
C2—C7 | 1.389 (5) | C20—C25 | 1.387 (5) |
C3—C4 | 1.382 (5) | C21—C22 | 1.405 (6) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.365 (7) | C22—C23 | 1.364 (9) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.363 (7) | C23—C24 | 1.349 (8) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—C7 | 1.387 (6) | C24—C25 | 1.381 (6) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C13 | 1.369 (6) | C26—C27 | 1.455 (12) |
C8—C9 | 1.387 (5) | C27—H27A | 0.9600 |
C9—C10 | 1.376 (7) | C27—H27B | 0.9600 |
C9—H9 | 0.9300 | C27—H27C | 0.9600 |
C10—C11 | 1.353 (9) | ||
P2—Ag1—P1 | 144.82 (3) | C11—C10—C9 | 121.2 (5) |
P2—Ag1—O1 | 106.05 (8) | C11—C10—H10 | 119.4 |
P1—Ag1—O1 | 102.83 (8) | C9—C10—H10 | 119.4 |
P2—Ag1—O2 | 129.40 (7) | C10—C11—C12 | 120.1 (5) |
P1—Ag1—O2 | 85.19 (7) | C10—C11—H11 | 119.9 |
O1—Ag1—O2 | 47.95 (10) | C12—C11—H11 | 119.9 |
P2—Ag1—Ag1i | 90.06 (2) | C11—C12—C13 | 119.8 (6) |
P1—Ag1—Ag1i | 78.39 (2) | C11—C12—H12 | 120.1 |
O1—Ag1—Ag1i | 143.11 (8) | C13—C12—H12 | 120.1 |
O2—Ag1—Ag1i | 96.21 (7) | C8—C13—C12 | 120.2 (5) |
C8—P1—C2 | 104.87 (17) | C8—C13—H13 | 119.9 |
C8—P1—C1 | 104.07 (17) | C12—C13—H13 | 119.9 |
C2—P1—C1 | 102.52 (15) | C19—C14—C15 | 118.5 (3) |
C8—P1—Ag1 | 121.84 (12) | C19—C14—P2 | 119.5 (3) |
C2—P1—Ag1 | 113.54 (11) | C15—C14—P2 | 121.4 (3) |
C1—P1—Ag1 | 107.99 (11) | C14—C15—C16 | 119.8 (4) |
C20—P2—C14 | 103.94 (16) | C14—C15—H15 | 120.1 |
C20—P2—C1i | 105.18 (17) | C16—C15—H15 | 120.1 |
C14—P2—C1i | 103.96 (16) | C17—C16—C15 | 120.7 (4) |
C20—P2—Ag1 | 118.75 (13) | C17—C16—H16 | 119.7 |
C14—P2—Ag1 | 110.93 (11) | C15—C16—H16 | 119.7 |
C1i—P2—Ag1 | 112.72 (11) | C16—C17—C18 | 120.4 (4) |
O2—N1—O1 | 114.1 (3) | C16—C17—H17 | 119.8 |
N1—O1—Ag1 | 99.1 (2) | C18—C17—H17 | 119.8 |
N1—O2—Ag1 | 98.8 (2) | C17—C18—C19 | 119.9 (4) |
P1—C1—P2i | 110.85 (18) | C17—C18—H18 | 120.1 |
P1—C1—H1A | 109.5 | C19—C18—H18 | 120.1 |
P2i—C1—H1A | 109.5 | C18—C19—C14 | 120.6 (4) |
P1—C1—H1B | 109.5 | C18—C19—H19 | 119.7 |
P2i—C1—H1B | 109.5 | C14—C19—H19 | 119.7 |
H1A—C1—H1B | 108.1 | C21—C20—C25 | 119.4 (4) |
C3—C2—C7 | 117.9 (3) | C21—C20—P2 | 119.4 (3) |
C3—C2—P1 | 119.7 (3) | C25—C20—P2 | 121.1 (3) |
C7—C2—P1 | 122.3 (3) | C20—C21—C22 | 119.3 (5) |
C4—C3—C2 | 120.9 (4) | C20—C21—H21 | 120.3 |
C4—C3—H3 | 119.6 | C22—C21—H21 | 120.3 |
C2—C3—H3 | 119.6 | C23—C22—C21 | 119.9 (6) |
C5—C4—C3 | 120.2 (4) | C23—C22—H22 | 120.1 |
C5—C4—H4 | 119.9 | C21—C22—H22 | 120.1 |
C3—C4—H4 | 119.9 | C24—C23—C22 | 121.0 (5) |
C6—C5—C4 | 120.2 (4) | C24—C23—H23 | 119.5 |
C6—C5—H5 | 119.9 | C22—C23—H23 | 119.5 |
C4—C5—H5 | 119.9 | C23—C24—C25 | 120.0 (5) |
C5—C6—C7 | 120.2 (4) | C23—C24—H24 | 120.0 |
C5—C6—H6 | 119.9 | C25—C24—H24 | 120.0 |
C7—C6—H6 | 119.9 | C24—C25—C20 | 120.4 (5) |
C6—C7—C2 | 120.6 (4) | C24—C25—H25 | 119.8 |
C6—C7—H7 | 119.7 | C20—C25—H25 | 119.8 |
C2—C7—H7 | 119.7 | N2—C26—C27 | 178.9 (11) |
C13—C8—C9 | 119.1 (4) | C26—C27—H27A | 109.5 |
C13—C8—P1 | 118.6 (3) | C26—C27—H27B | 109.5 |
C9—C8—P1 | 122.2 (3) | H27A—C27—H27B | 109.5 |
C10—C9—C8 | 119.5 (5) | C26—C27—H27C | 109.5 |
C10—C9—H9 | 120.2 | H27A—C27—H27C | 109.5 |
C8—C9—H9 | 120.2 | H27B—C27—H27C | 109.5 |
P2—Ag1—P1—C8 | 11.22 (16) | C4—C5—C6—C7 | 0.3 (7) |
O1—Ag1—P1—C8 | 155.83 (16) | C5—C6—C7—C2 | −1.1 (6) |
O2—Ag1—P1—C8 | −159.29 (16) | C3—C2—C7—C6 | 0.8 (5) |
Ag1i—Ag1—P1—C8 | −61.93 (14) | P1—C2—C7—C6 | −175.4 (3) |
P2—Ag1—P1—C2 | −115.66 (13) | C2—P1—C8—C13 | 128.7 (3) |
O1—Ag1—P1—C2 | 28.95 (15) | C1—P1—C8—C13 | −124.0 (3) |
O2—Ag1—P1—C2 | 73.83 (14) | Ag1—P1—C8—C13 | −1.9 (4) |
Ag1i—Ag1—P1—C2 | 171.19 (13) | C2—P1—C8—C9 | −52.9 (4) |
P2—Ag1—P1—C1 | 131.39 (12) | C1—P1—C8—C9 | 54.4 (4) |
O1—Ag1—P1—C1 | −84.01 (14) | Ag1—P1—C8—C9 | 176.5 (3) |
O2—Ag1—P1—C1 | −39.13 (13) | C13—C8—C9—C10 | −0.1 (7) |
Ag1i—Ag1—P1—C1 | 58.23 (12) | P1—C8—C9—C10 | −178.5 (4) |
P1—Ag1—P2—C20 | 156.55 (14) | C8—C9—C10—C11 | 1.1 (9) |
O1—Ag1—P2—C20 | 12.54 (16) | C9—C10—C11—C12 | −0.6 (11) |
O2—Ag1—P2—C20 | −35.73 (17) | C10—C11—C12—C13 | −0.8 (11) |
Ag1i—Ag1—P2—C20 | −133.82 (14) | C9—C8—C13—C12 | −1.3 (7) |
P1—Ag1—P2—C14 | 36.27 (14) | P1—C8—C13—C12 | 177.1 (4) |
O1—Ag1—P2—C14 | −107.73 (15) | C11—C12—C13—C8 | 1.8 (9) |
O2—Ag1—P2—C14 | −156.00 (15) | C20—P2—C14—C19 | 163.7 (3) |
Ag1i—Ag1—P2—C14 | 105.91 (12) | C1i—P2—C14—C19 | 53.8 (3) |
P1—Ag1—P2—C1i | −79.84 (14) | Ag1—P2—C14—C19 | −67.6 (3) |
O1—Ag1—P2—C1i | 136.15 (15) | C20—P2—C14—C15 | −25.3 (3) |
O2—Ag1—P2—C1i | 87.89 (16) | C1i—P2—C14—C15 | −135.1 (3) |
Ag1i—Ag1—P2—C1i | −10.21 (13) | Ag1—P2—C14—C15 | 103.5 (3) |
O2—N1—O1—Ag1 | −2.0 (4) | C19—C14—C15—C16 | −0.2 (5) |
P2—Ag1—O1—N1 | −127.9 (2) | P2—C14—C15—C16 | −171.3 (3) |
P1—Ag1—O1—N1 | 72.4 (3) | C14—C15—C16—C17 | 1.2 (6) |
O2—Ag1—O1—N1 | 1.2 (2) | C15—C16—C17—C18 | −1.8 (7) |
Ag1i—Ag1—O1—N1 | −15.2 (3) | C16—C17—C18—C19 | 1.3 (7) |
O1—N1—O2—Ag1 | 2.0 (4) | C17—C18—C19—C14 | −0.2 (6) |
P2—Ag1—O2—N1 | 73.8 (3) | C15—C14—C19—C18 | −0.3 (6) |
P1—Ag1—O2—N1 | −113.3 (2) | P2—C14—C19—C18 | 171.0 (3) |
O1—Ag1—O2—N1 | −1.2 (2) | C14—P2—C20—C21 | 113.3 (3) |
Ag1i—Ag1—O2—N1 | 169.0 (2) | C1i—P2—C20—C21 | −137.8 (3) |
C8—P1—C1—P2i | 62.7 (2) | Ag1—P2—C20—C21 | −10.5 (4) |
C2—P1—C1—P2i | 171.77 (18) | C14—P2—C20—C25 | −64.7 (4) |
Ag1—P1—C1—P2i | −68.08 (18) | C1i—P2—C20—C25 | 44.2 (4) |
C8—P1—C2—C3 | 157.2 (3) | Ag1—P2—C20—C25 | 171.5 (3) |
C1—P1—C2—C3 | 48.7 (3) | C25—C20—C21—C22 | 1.2 (7) |
Ag1—P1—C2—C3 | −67.5 (3) | P2—C20—C21—C22 | −176.8 (4) |
C8—P1—C2—C7 | −26.7 (3) | C20—C21—C22—C23 | −2.5 (9) |
C1—P1—C2—C7 | −135.1 (3) | C21—C22—C23—C24 | 2.1 (10) |
Ag1—P1—C2—C7 | 108.7 (3) | C22—C23—C24—C25 | −0.5 (9) |
C7—C2—C3—C4 | 0.3 (6) | C23—C24—C25—C20 | −0.8 (8) |
P1—C2—C3—C4 | 176.6 (3) | C21—C20—C25—C24 | 0.4 (7) |
C2—C3—C4—C5 | −1.1 (6) | P2—C20—C25—C24 | 178.4 (4) |
C3—C4—C5—C6 | 0.8 (7) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(NO2)2(C25H22P2)2]·2C2H3N |
Mr | 1158.60 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 12.1390 (11), 11.1247 (9), 20.0350 (18) |
β (°) | 95.543 (1) |
V (Å3) | 2692.9 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.89 |
Crystal size (mm) | 0.40 × 0.35 × 0.33 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.717, 0.757 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13205, 4752, 3845 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.090, 1.07 |
No. of reflections | 4752 |
No. of parameters | 308 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.01, −0.46 |
Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No. 21171119), the National High Technology Research and Development Program 863 of China (2012AA063201), the Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901 and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The coordination chemistry of silver(I) complexes has been extensively studied because of their luminescence properties and potential applications in catalysis, photography, antimicrobial activities and electrochemical processes (Bowmaker et al., 1993; Cui, Hu et al., 2010; Cui, Jin et al., 2010; Jin, Hu et al., 2010; Jin, Song et al., 2010; Meijboom et al., 2009). Recently, some silver(I) complexes containing phosphine ligands and coordinated anions have been reported (Jin et al., 2008; Song et al., 2010). Continuing these efforts, we synthesized a new complex using AgNO2, bis(diphenylphosphino)methane (dppm) and 1,2-bis(4-pyridyl)ethane, the title compound [Ag2(dppm)2(NO2)2] . 2(CH3CN), and the structure is reported here.
In the title compound two silver atoms are bridged by two dppm ligands, giving a centrosymmetric dimer (Fig. 1) having a Ag···Ag distance of 3.1809 (5) Å, which is longer than that found in the analogous complex [Ag2L2](SO3CF3)2 (L = 4'-phenylterpyridine) [2.9452 (4) Å] (Ma et al., 2009). Each of the two NO2- anions chelates an Ag atom with Ag—O bond distances of 2.550 (3) and 2.567 (3) Å, so each Ag atom is tetracoordinated. These values compare with 2.694 (4) and 2.559 (5) Å in a similar crystal [AgNO2(dppm)]2, which was synthesized in methanol (Effendy et al., 2004). In the title complex, the P2—Ag1—P1 angle is 144.82 (3)°, the O1—Ag1—O2 angle is 47.98 (10)°, while the P—Ag1—O angles are in the range of 85.18 (7)–129.41 (7)°, indicating a very distorted tetrahedral stereochemistry about the two silver(I) atoms. The Ag1—P1 and Ag1—P2 bond lengths are 2.4747 (8) and 2.4395 (9) Å, which are both longer than the Ag—P bond found in [Ag(NCS)(C25H22P2)]n (Song et al., 2010), which is analogous to the title compound, synthesized using a similar reaction in the presence of 1,10-phenanthroline.