metal-organic compounds
μ-Chlorido-bis[(dimethyl sulfoxide-κO)bis(triphenylphosphane-κP)silver(I)] nitrate
aCollege of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000, People's Republic of China
*Correspondence e-mail: liyunhua@lzu.edu.cn
The 2Cl(C2H6OS)2(C18H15P)4]NO3, comprises one nitrate anion and one half of the binuclear complex cation, the other half being completed by inversion symmetry. The AgI atom has a distorted (ClOP2) coordination sphere. Weak intermolecular C—H⋯O interactions between the cation and the O atoms of the nitrate counter-anion help to consolidate the crystal packing.
of the title salt, [AgKeywords: crystal structure; silver(I); solvent coordination.
CCDC reference: 1455947
Structure description
The AgI atom in the complex cation is coordinated by two P atoms from triphenylphosphine ligands, the bridging Cl atom, and the O atom from the dimethyl sulfoxide ligand in a distorted tetrahedral environment [bond angle range 95.62 (11)–120.71 (4) °; Fig. 1]. The nitrate anion does not coordinate to the metal cation and is statistically disordered about a centre of inversion. The molecular configuration of the cation is stabilized by an intramolecular hydrogen bond between a phenyl CH group (C1) and the dimethyl sulfoxide O atom (O4). Other intermolecular C—H⋯O hydrogen-bonding interactions involving the phenyl and methyl H atoms of the cation and neighbouring anions (Table 1) lead to the formation of a three-dimensional network structure. The crystal structures of similar silver compounds were reported by Cassel (1979) and Bowmaker et al. (1993).
Synthesis and crystallization
Reaction of AgNO3 (85 mg, 0.5 mmol) with PPh3 (262 mg, 1 mmol) in chloroform/DMSO/ethanol/water (12 ml, v/v/v/v = 1:1:1:1) under ultrasonic treatment (160 W, 40 kHz, 373 K, 10 min) led to a colourless solution that was allowed to slowly evaporate at room temperature for two weeks to give colourless crystals of the title compound. Yield: ca 55% based on AgNO3.
Refinement
Crystal data, data collection and structure . The nitrate counter-anion (N1, O1, O2, O3) is disordered about an inversion centre and each of the atoms consequently has an occupancy of 0.5.
details are summarized in Table 2Structural data
CCDC reference: 1455947
10.1107/S2414314616003321/wm4005sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616003321/wm4005Isup2.hkl
Reaction of AgNO3 (85 mg, 0.5 mmol) with PPh3 (262 mg, 1 mmol) in chloroform/DMSO/ethanol/water (12 ml, v/v/v/v = 1:1:1:1) under ultrasonic treatment (160 W, 40 kHz, 373 K, 10 min) led to a colourless solution that was allowed to slowly evaporate at room temperature for two weeks to give colourless crystals of the title compound. Yield: ca55% based on AgNO3.
All hydrogen atoms were located in geometrically idealized positions but were constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) (aromatic H atoms) and 0.96 Å Uiso(H) = 1.5Ueq(C) (methyl H atoms). The nitrate counter anion (N1, O1, O2, O3) is disordered about an inversion centre and each of the atoms consequently has an occupancy of 0.5.
Reaction of AgNO3 (85 mg, 0.5 mmol) with PPh3 (262 mg, 1 mmol) in chloroform/DMSO/ethanol/water (12 ml, v/v/v/v = 1:1:1:1) under ultrasonic treatment (160 W, 40 kHz, 373 K, 10 min) led to a colourless solution that was allowed to slowly evaporate at room temperature for two weeks to give colourless crystals of the title compound. Yield: ca 55% based on AgNO3.
Crystal data, data collection and structure
details are summarized in Table 2. The nitrate counter-anion (N1, O1, O2, O3) is disordered about an inversion centre and each of the atoms consequently has an occupancy of 0.5.The AgI atom in the complex cation is coordinated by two P atoms from triphenylphosphine ligands, the bridging Cl atom, and one O atom from the dimethyl sulfoxide ligand in a distorted tetrahedral environment [bond angle range 95.62 (11)–120.71 (4) °; Fig. 1]. The nitrate anion does not coordinate to the metal cation and is statistically disordered about a centre of inversion. The molecular configuration of the cation is stabilized by an intramolecular hydrogen bond between a phenyl CH group (C1) and the dimethyl sulfoxide O atom (O4). Other intermolecular C—H···O hydrogen-bonding interactions involving the phenyl and methyl H atoms of the cation and neighbouring anions (Table 1) lead to the formation of a three-dimensional network structure. The crystal structures of similar silver compounds were reported by Cassel (1979) and Bowmaker et al. (1993).
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structures of the cation and anion in the title structure. Displacement ellipsoids are displayed at the 50% probability level. Non-labelled symmetry-related atoms are generated by symmetry code (−x, −y, −z + 1). |
[Ag2Cl(C2H6OS)2(C18H15P)4]NO3 | Z = 1 |
Mr = 1518.56 | F(000) = 778 |
Triclinic, P1 | Dx = 1.499 Mg m−3 |
a = 12.440 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.070 (3) Å | Cell parameters from 4355 reflections |
c = 13.579 (3) Å | θ = 2.3–28.4° |
α = 93.489 (5)° | µ = 0.83 mm−1 |
β = 117.157 (4)° | T = 173 K |
γ = 115.354 (4)° | Block, colourless |
V = 1682.6 (7) Å3 | 0.3 × 0.15 × 0.12 mm |
Agilent CCD Xcalibur diffractometer | 5941 independent reflections |
Radiation source: sealed X-ray tube | 5298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −14→14 |
Tmin = 0.861, Tmax = 0.905 | k = −10→15 |
8521 measured reflections | l = −16→13 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0478P)2 + 6.8934P] where P = (Fo2 + 2Fc2)/3 |
5868 reflections | (Δ/σ)max = 0.004 |
430 parameters | Δρmax = 2.39 e Å−3 |
6 restraints | Δρmin = −2.12 e Å−3 |
[Ag2Cl(C2H6OS)2(C18H15P)4]NO3 | γ = 115.354 (4)° |
Mr = 1518.56 | V = 1682.6 (7) Å3 |
Triclinic, P1 | Z = 1 |
a = 12.440 (3) Å | Mo Kα radiation |
b = 13.070 (3) Å | µ = 0.83 mm−1 |
c = 13.579 (3) Å | T = 173 K |
α = 93.489 (5)° | 0.3 × 0.15 × 0.12 mm |
β = 117.157 (4)° |
Agilent CCD Xcalibur diffractometer | 5941 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 5298 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 0.905 | Rint = 0.062 |
8521 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 6 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.12 | Δρmax = 2.39 e Å−3 |
5868 reflections | Δρmin = −2.12 e Å−3 |
430 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.04619 (4) | 0.07560 (4) | 0.71100 (4) | 0.03575 (17) | |
Cl1 | 0.0000 | 0.0000 | 0.5000 | 0.0484 (6) | |
S1 | −0.26857 (16) | −0.19692 (13) | 0.61116 (14) | 0.0371 (4) | |
P1 | 0.03902 (14) | 0.25182 (12) | 0.76647 (13) | 0.0288 (3) | |
P2 | 0.23582 (14) | 0.03943 (12) | 0.82202 (12) | 0.0251 (3) | |
O4 | −0.1809 (5) | −0.0643 (3) | 0.6687 (4) | 0.0434 (11) | |
C1 | −0.2383 (6) | 0.1576 (5) | 0.5935 (5) | 0.0388 (14) | |
H1 | −0.2448 | 0.0841 | 0.5942 | 0.047* | |
C2 | −0.3545 (6) | 0.1622 (6) | 0.5162 (6) | 0.0492 (17) | |
H2 | −0.4390 | 0.0920 | 0.4639 | 0.059* | |
C3 | −0.3452 (7) | 0.2706 (6) | 0.5167 (6) | 0.0474 (17) | |
H3 | −0.4243 | 0.2733 | 0.4649 | 0.057* | |
C4 | −0.2228 (7) | 0.3735 (6) | 0.5912 (6) | 0.0419 (15) | |
H4 | −0.2178 | 0.4466 | 0.5910 | 0.050* | |
C5 | −0.1055 (6) | 0.3694 (5) | 0.6674 (5) | 0.0360 (14) | |
H5 | −0.0208 | 0.4402 | 0.7179 | 0.043* | |
C6 | −0.1124 (6) | 0.2614 (5) | 0.6697 (5) | 0.0311 (12) | |
C7 | −0.0046 (7) | 0.3372 (6) | 0.9310 (6) | 0.0418 (15) | |
H7 | −0.0751 | 0.3426 | 0.8695 | 0.050* | |
C8 | 0.0251 (8) | 0.3725 (6) | 1.0423 (7) | 0.0527 (18) | |
H8 | −0.0258 | 0.4005 | 1.0557 | 0.063* | |
C9 | 0.1299 (8) | 0.3659 (6) | 1.1330 (6) | 0.0483 (17) | |
H9 | 0.1520 | 0.3915 | 1.2087 | 0.058* | |
C10 | 0.2021 (8) | 0.3221 (6) | 1.1131 (6) | 0.0500 (17) | |
H10 | 0.2733 | 0.3177 | 1.1750 | 0.060* | |
C11 | 0.1699 (7) | 0.2845 (6) | 1.0020 (6) | 0.0434 (15) | |
H11 | 0.2172 | 0.2519 | 0.9885 | 0.052* | |
C12 | 0.0678 (6) | 0.2942 (5) | 0.9094 (5) | 0.0326 (13) | |
C13 | 0.2916 (6) | 0.4746 (5) | 0.8694 (5) | 0.0322 (13) | |
H13 | 0.2912 | 0.4803 | 0.9378 | 0.039* | |
C14 | 0.4001 (6) | 0.5616 (5) | 0.8674 (5) | 0.0393 (14) | |
H14 | 0.4735 | 0.6262 | 0.9346 | 0.047* | |
C15 | 0.4027 (7) | 0.5555 (6) | 0.7684 (6) | 0.0423 (15) | |
H15 | 0.4777 | 0.6157 | 0.7681 | 0.051* | |
C16 | 0.2943 (7) | 0.4603 (6) | 0.6687 (6) | 0.0402 (15) | |
H16 | 0.2947 | 0.4559 | 0.6002 | 0.048* | |
C17 | 0.1862 (6) | 0.3723 (5) | 0.6717 (5) | 0.0331 (13) | |
H17 | 0.1135 | 0.3070 | 0.6050 | 0.040* | |
C18 | 0.1828 (5) | 0.3786 (5) | 0.7719 (5) | 0.0271 (12) | |
C19 | 0.1706 (6) | 0.0051 (5) | 0.9879 (5) | 0.0352 (13) | |
H19 | 0.0783 | −0.0339 | 0.9242 | 0.042* | |
C20 | 0.1975 (7) | 0.0112 (5) | 1.0988 (6) | 0.0385 (14) | |
H20 | 0.1235 | −0.0256 | 1.1104 | 0.046* | |
C21 | 0.3331 (7) | 0.0716 (5) | 1.1915 (5) | 0.0353 (13) | |
H21 | 0.3512 | 0.0756 | 1.2665 | 0.042* | |
C22 | 0.4416 (6) | 0.1257 (5) | 1.1763 (5) | 0.0352 (14) | |
H22 | 0.5335 | 0.1680 | 1.2407 | 0.042* | |
C23 | 0.4167 (6) | 0.1187 (5) | 1.0660 (5) | 0.0283 (12) | |
H23 | 0.4915 | 0.1555 | 1.0554 | 0.034* | |
C24 | 0.2808 (5) | 0.0571 (4) | 0.9716 (4) | 0.0241 (11) | |
C25 | 0.4200 (6) | 0.2558 (5) | 0.8256 (5) | 0.0308 (12) | |
H25 | 0.3540 | 0.2763 | 0.8173 | 0.037* | |
C26 | 0.5389 (6) | 0.3362 (5) | 0.8317 (5) | 0.0373 (14) | |
H26 | 0.5541 | 0.4117 | 0.8285 | 0.045* | |
C27 | 0.6363 (7) | 0.3075 (5) | 0.8425 (5) | 0.0391 (14) | |
H27 | 0.7175 | 0.3628 | 0.8467 | 0.047* | |
C28 | 0.6125 (7) | 0.1958 (6) | 0.8472 (6) | 0.0439 (16) | |
H28 | 0.6779 | 0.1753 | 0.8538 | 0.053* | |
C29 | 0.4949 (6) | 0.1148 (5) | 0.8422 (6) | 0.0379 (14) | |
H29 | 0.4805 | 0.0396 | 0.8459 | 0.046* | |
C30 | 0.3966 (6) | 0.1437 (5) | 0.8317 (4) | 0.0256 (11) | |
C31 | 0.2194 (6) | −0.1782 (5) | 0.8462 (5) | 0.0313 (12) | |
H31 | 0.2412 | −0.1516 | 0.9216 | 0.038* | |
C32 | 0.1942 (7) | −0.2895 (5) | 0.8046 (6) | 0.0395 (14) | |
H32 | 0.1992 | −0.3379 | 0.8519 | 0.047* | |
C33 | 0.1624 (6) | −0.3291 (5) | 0.6954 (6) | 0.0377 (14) | |
H33 | 0.1449 | −0.4048 | 0.6677 | 0.045* | |
C34 | 0.1555 (6) | −0.2580 (5) | 0.6247 (5) | 0.0341 (13) | |
H34 | 0.1343 | −0.2854 | 0.5497 | 0.041* | |
C35 | 0.1797 (6) | −0.1470 (5) | 0.6648 (5) | 0.0315 (12) | |
H35 | 0.1741 | −0.0993 | 0.6168 | 0.038* | |
C36 | 0.2125 (5) | −0.1056 (4) | 0.7768 (5) | 0.0264 (11) | |
C37 | −0.3516 (8) | −0.2205 (7) | 0.4597 (6) | 0.0544 (19) | |
H37A | −0.4095 | −0.3048 | 0.4185 | 0.082* | |
H37B | −0.2815 | −0.1847 | 0.4404 | 0.082* | |
H37C | −0.4091 | −0.1851 | 0.4375 | 0.082* | |
C38 | −0.1502 (7) | −0.2429 (6) | 0.6253 (6) | 0.0446 (16) | |
H38A | −0.2008 | −0.3279 | 0.5897 | 0.067* | |
H38B | −0.0821 | −0.2220 | 0.7065 | 0.067* | |
H38C | −0.1029 | −0.2040 | 0.5873 | 0.067* | |
N1 | 0.511 (4) | 0.506 (6) | 0.5173 (15) | 0.035 (3) | 0.50 |
O1 | 0.5480 (17) | 0.4748 (12) | 0.4527 (14) | 0.070 (3) | 0.50 |
O2 | 0.4006 (13) | 0.5016 (13) | 0.4696 (13) | 0.063 (3) | 0.50 |
O3 | 0.5750 (14) | 0.5105 (11) | 0.6173 (10) | 0.082 (3) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0243 (2) | 0.0216 (2) | 0.0448 (3) | 0.01288 (18) | 0.0063 (2) | 0.00570 (18) |
Cl1 | 0.0594 (15) | 0.0553 (14) | 0.0419 (12) | 0.0347 (12) | 0.0295 (12) | 0.0205 (11) |
S1 | 0.0315 (8) | 0.0279 (7) | 0.0414 (9) | 0.0084 (6) | 0.0193 (7) | 0.0046 (6) |
P1 | 0.0220 (7) | 0.0212 (7) | 0.0362 (8) | 0.0121 (6) | 0.0098 (6) | 0.0078 (6) |
P2 | 0.0242 (7) | 0.0225 (7) | 0.0265 (7) | 0.0146 (6) | 0.0099 (6) | 0.0066 (5) |
O4 | 0.042 (2) | 0.025 (2) | 0.057 (3) | 0.0083 (19) | 0.032 (2) | 0.0002 (19) |
C1 | 0.027 (3) | 0.031 (3) | 0.045 (4) | 0.013 (3) | 0.012 (3) | 0.012 (3) |
C2 | 0.023 (3) | 0.045 (4) | 0.051 (4) | 0.010 (3) | 0.007 (3) | 0.013 (3) |
C3 | 0.033 (3) | 0.065 (5) | 0.050 (4) | 0.035 (3) | 0.017 (3) | 0.027 (4) |
C4 | 0.046 (4) | 0.043 (4) | 0.048 (4) | 0.033 (3) | 0.023 (3) | 0.018 (3) |
C5 | 0.032 (3) | 0.032 (3) | 0.039 (3) | 0.019 (3) | 0.013 (3) | 0.011 (3) |
C6 | 0.025 (3) | 0.032 (3) | 0.038 (3) | 0.020 (2) | 0.014 (3) | 0.011 (2) |
C7 | 0.044 (4) | 0.046 (4) | 0.047 (4) | 0.028 (3) | 0.028 (3) | 0.022 (3) |
C8 | 0.070 (5) | 0.055 (4) | 0.070 (5) | 0.042 (4) | 0.052 (4) | 0.032 (4) |
C9 | 0.066 (5) | 0.041 (4) | 0.045 (4) | 0.023 (3) | 0.037 (4) | 0.017 (3) |
C10 | 0.049 (4) | 0.057 (4) | 0.040 (4) | 0.027 (4) | 0.020 (3) | 0.023 (3) |
C11 | 0.039 (4) | 0.043 (4) | 0.052 (4) | 0.024 (3) | 0.024 (3) | 0.019 (3) |
C12 | 0.030 (3) | 0.020 (3) | 0.038 (3) | 0.010 (2) | 0.015 (3) | 0.010 (2) |
C13 | 0.032 (3) | 0.028 (3) | 0.030 (3) | 0.015 (2) | 0.012 (3) | 0.006 (2) |
C14 | 0.034 (3) | 0.030 (3) | 0.039 (3) | 0.009 (3) | 0.016 (3) | 0.003 (3) |
C15 | 0.033 (3) | 0.035 (3) | 0.063 (4) | 0.020 (3) | 0.025 (3) | 0.022 (3) |
C16 | 0.054 (4) | 0.043 (4) | 0.043 (4) | 0.033 (3) | 0.032 (3) | 0.020 (3) |
C17 | 0.036 (3) | 0.025 (3) | 0.030 (3) | 0.015 (3) | 0.013 (3) | 0.006 (2) |
C18 | 0.022 (3) | 0.022 (3) | 0.039 (3) | 0.015 (2) | 0.014 (2) | 0.010 (2) |
C19 | 0.031 (3) | 0.037 (3) | 0.033 (3) | 0.017 (3) | 0.014 (3) | 0.007 (3) |
C20 | 0.038 (3) | 0.038 (3) | 0.048 (4) | 0.018 (3) | 0.029 (3) | 0.017 (3) |
C21 | 0.045 (4) | 0.044 (3) | 0.033 (3) | 0.030 (3) | 0.024 (3) | 0.016 (3) |
C22 | 0.032 (3) | 0.035 (3) | 0.026 (3) | 0.019 (3) | 0.006 (3) | 0.005 (2) |
C23 | 0.027 (3) | 0.029 (3) | 0.032 (3) | 0.017 (2) | 0.016 (2) | 0.009 (2) |
C24 | 0.025 (3) | 0.022 (3) | 0.027 (3) | 0.016 (2) | 0.012 (2) | 0.007 (2) |
C25 | 0.034 (3) | 0.027 (3) | 0.031 (3) | 0.017 (2) | 0.016 (3) | 0.009 (2) |
C26 | 0.042 (3) | 0.024 (3) | 0.040 (3) | 0.017 (3) | 0.018 (3) | 0.010 (3) |
C27 | 0.034 (3) | 0.036 (3) | 0.045 (4) | 0.017 (3) | 0.021 (3) | 0.016 (3) |
C28 | 0.038 (3) | 0.046 (4) | 0.064 (4) | 0.028 (3) | 0.032 (3) | 0.026 (3) |
C29 | 0.036 (3) | 0.031 (3) | 0.048 (4) | 0.023 (3) | 0.019 (3) | 0.016 (3) |
C30 | 0.027 (3) | 0.029 (3) | 0.021 (3) | 0.017 (2) | 0.011 (2) | 0.008 (2) |
C31 | 0.034 (3) | 0.029 (3) | 0.032 (3) | 0.018 (3) | 0.016 (3) | 0.010 (2) |
C32 | 0.045 (4) | 0.031 (3) | 0.049 (4) | 0.023 (3) | 0.025 (3) | 0.016 (3) |
C33 | 0.032 (3) | 0.027 (3) | 0.053 (4) | 0.018 (3) | 0.021 (3) | 0.006 (3) |
C34 | 0.032 (3) | 0.033 (3) | 0.032 (3) | 0.017 (3) | 0.015 (3) | 0.003 (2) |
C35 | 0.035 (3) | 0.035 (3) | 0.029 (3) | 0.023 (3) | 0.016 (3) | 0.012 (2) |
C36 | 0.022 (3) | 0.022 (3) | 0.030 (3) | 0.013 (2) | 0.009 (2) | 0.004 (2) |
C37 | 0.052 (4) | 0.053 (4) | 0.037 (4) | 0.026 (4) | 0.010 (3) | 0.009 (3) |
C38 | 0.043 (4) | 0.037 (3) | 0.046 (4) | 0.023 (3) | 0.017 (3) | 0.010 (3) |
N1 | 0.019 (10) | 0.022 (10) | 0.037 (9) | −0.002 (11) | 0.010 (12) | −0.010 (16) |
O1 | 0.087 (9) | 0.061 (8) | 0.107 (8) | 0.044 (8) | 0.078 (9) | 0.026 (9) |
O2 | 0.043 (6) | 0.072 (9) | 0.093 (9) | 0.036 (6) | 0.043 (6) | 0.038 (9) |
O3 | 0.073 (8) | 0.080 (8) | 0.051 (6) | 0.026 (7) | 0.015 (6) | 0.019 (6) |
Ag1—Cl1 | 2.6799 (8) | C17—H17 | 0.9300 |
Ag1—P1 | 2.4303 (15) | C17—C18 | 1.379 (8) |
Ag1—P2 | 2.4200 (14) | C19—H19 | 0.9300 |
Ag1—O4 | 2.371 (4) | C19—C20 | 1.374 (9) |
Cl1—Ag1i | 2.6799 (8) | C19—C24 | 1.374 (8) |
S1—O4 | 1.497 (4) | C20—H20 | 0.9300 |
S1—C37 | 1.762 (7) | C20—C21 | 1.362 (9) |
S1—C38 | 1.755 (7) | C21—H21 | 0.9300 |
P1—C6 | 1.804 (5) | C21—C22 | 1.349 (9) |
P1—C12 | 1.808 (6) | C22—H22 | 0.9300 |
P1—C18 | 1.810 (6) | C22—C23 | 1.372 (8) |
P2—C24 | 1.813 (5) | C23—H23 | 0.9300 |
P2—C30 | 1.811 (6) | C23—C24 | 1.371 (7) |
P2—C36 | 1.811 (5) | C25—H25 | 0.9300 |
C1—H1 | 0.9300 | C25—C26 | 1.358 (9) |
C1—C2 | 1.376 (9) | C25—C30 | 1.381 (7) |
C1—C6 | 1.377 (8) | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C26—C27 | 1.365 (9) |
C2—C3 | 1.370 (9) | C27—H27 | 0.9300 |
C3—H3 | 0.9300 | C27—C28 | 1.371 (8) |
C3—C4 | 1.351 (9) | C28—H28 | 0.9300 |
C4—H4 | 0.9300 | C28—C29 | 1.357 (9) |
C4—C5 | 1.378 (8) | C29—H29 | 0.9300 |
C5—H5 | 0.9300 | C29—C30 | 1.379 (8) |
C5—C6 | 1.381 (8) | C31—H31 | 0.9300 |
C7—H7 | 0.9300 | C31—C32 | 1.372 (8) |
C7—C8 | 1.376 (10) | C31—C36 | 1.379 (8) |
C7—C12 | 1.365 (9) | C32—H32 | 0.9300 |
C8—H8 | 0.9300 | C32—C33 | 1.348 (9) |
C8—C9 | 1.365 (10) | C33—H33 | 0.9300 |
C9—H9 | 0.9300 | C33—C34 | 1.375 (9) |
C9—C10 | 1.361 (10) | C34—H34 | 0.9300 |
C10—H10 | 0.9300 | C34—C35 | 1.368 (8) |
C10—C11 | 1.367 (10) | C35—H35 | 0.9300 |
C11—H11 | 0.9300 | C35—C36 | 1.384 (8) |
C11—C12 | 1.382 (9) | C37—H37A | 0.9600 |
C13—H13 | 0.9300 | C37—H37B | 0.9600 |
C13—C14 | 1.356 (9) | C37—H37C | 0.9600 |
C13—C18 | 1.366 (8) | C38—H38A | 0.9600 |
C14—H14 | 0.9300 | C38—H38B | 0.9600 |
C14—C15 | 1.357 (9) | C38—H38C | 0.9600 |
C15—H15 | 0.9300 | N1—O1 | 1.27 (4) |
C15—C16 | 1.376 (9) | N1—O2 | 1.20 (4) |
C16—H16 | 0.9300 | N1—O3 | 1.20 (2) |
C16—C17 | 1.366 (9) | ||
P1—Ag1—Cl1 | 120.71 (4) | C18—C17—H17 | 119.4 |
P2—Ag1—Cl1 | 97.42 (4) | C13—C18—P1 | 124.8 (5) |
P2—Ag1—P1 | 125.89 (5) | C13—C18—C17 | 118.4 (5) |
O4—Ag1—Cl1 | 96.95 (11) | C17—C18—P1 | 116.6 (4) |
O4—Ag1—P1 | 95.62 (11) | C20—C19—H19 | 120.2 |
O4—Ag1—P2 | 117.80 (12) | C24—C19—H19 | 120.2 |
Ag1i—Cl1—Ag1 | 180.0 | C24—C19—C20 | 119.7 (6) |
O4—S1—C37 | 106.2 (3) | C19—C20—H20 | 120.2 |
O4—S1—C38 | 105.7 (3) | C21—C20—C19 | 119.5 (6) |
C38—S1—C37 | 97.4 (4) | C21—C20—H20 | 120.2 |
C6—P1—Ag1 | 118.66 (19) | C20—C21—H21 | 119.5 |
C6—P1—C12 | 104.4 (3) | C22—C21—C20 | 121.0 (6) |
C6—P1—C18 | 103.3 (3) | C22—C21—H21 | 119.5 |
C12—P1—Ag1 | 117.58 (19) | C21—C22—H22 | 119.9 |
C12—P1—C18 | 103.6 (3) | C21—C22—C23 | 120.2 (5) |
C18—P1—Ag1 | 107.40 (18) | C23—C22—H22 | 119.9 |
C24—P2—Ag1 | 111.65 (17) | C22—C23—H23 | 120.3 |
C30—P2—Ag1 | 112.26 (17) | C24—C23—C22 | 119.5 (5) |
C30—P2—C24 | 105.6 (2) | C24—C23—H23 | 120.3 |
C36—P2—Ag1 | 119.52 (17) | C19—C24—P2 | 116.7 (4) |
C36—P2—C24 | 102.2 (2) | C23—C24—P2 | 123.3 (4) |
C36—P2—C30 | 104.3 (2) | C23—C24—C19 | 120.1 (5) |
S1—O4—Ag1 | 130.5 (2) | C26—C25—H25 | 119.8 |
C2—C1—H1 | 119.9 | C26—C25—C30 | 120.4 (5) |
C2—C1—C6 | 120.2 (6) | C30—C25—H25 | 119.8 |
C6—C1—H1 | 119.9 | C25—C26—H26 | 119.6 |
C1—C2—H2 | 120.1 | C25—C26—C27 | 120.8 (5) |
C3—C2—C1 | 119.8 (6) | C27—C26—H26 | 119.6 |
C3—C2—H2 | 120.1 | C26—C27—H27 | 120.5 |
C2—C3—H3 | 119.5 | C26—C27—C28 | 119.0 (6) |
C4—C3—C2 | 121.0 (6) | C28—C27—H27 | 120.5 |
C4—C3—H3 | 119.5 | C27—C28—H28 | 119.5 |
C3—C4—H4 | 120.3 | C29—C28—C27 | 120.9 (6) |
C3—C4—C5 | 119.5 (6) | C29—C28—H28 | 119.5 |
C5—C4—H4 | 120.3 | C28—C29—H29 | 119.9 |
C4—C5—H5 | 119.6 | C28—C29—C30 | 120.2 (6) |
C4—C5—C6 | 120.7 (6) | C30—C29—H29 | 119.9 |
C6—C5—H5 | 119.6 | C25—C30—P2 | 118.6 (4) |
C1—C6—P1 | 118.9 (4) | C29—C30—P2 | 122.6 (4) |
C1—C6—C5 | 118.9 (5) | C29—C30—C25 | 118.7 (5) |
C5—C6—P1 | 122.2 (4) | C32—C31—H31 | 119.9 |
C8—C7—H7 | 119.4 | C32—C31—C36 | 120.3 (6) |
C12—C7—H7 | 119.4 | C36—C31—H31 | 119.9 |
C12—C7—C8 | 121.1 (6) | C31—C32—H32 | 119.8 |
C7—C8—H8 | 120.2 | C33—C32—C31 | 120.4 (6) |
C9—C8—C7 | 119.5 (7) | C33—C32—H32 | 119.8 |
C9—C8—H8 | 120.2 | C32—C33—H33 | 119.8 |
C8—C9—H9 | 119.9 | C32—C33—C34 | 120.3 (5) |
C10—C9—C8 | 120.3 (7) | C34—C33—H33 | 119.8 |
C10—C9—H9 | 119.9 | C33—C34—H34 | 120.0 |
C9—C10—H10 | 120.0 | C35—C34—C33 | 120.0 (6) |
C9—C10—C11 | 120.0 (7) | C35—C34—H34 | 120.0 |
C11—C10—H10 | 120.0 | C34—C35—H35 | 119.9 |
C10—C11—H11 | 119.6 | C34—C35—C36 | 120.1 (5) |
C10—C11—C12 | 120.8 (6) | C36—C35—H35 | 119.9 |
C12—C11—H11 | 119.6 | C31—C36—P2 | 123.3 (4) |
C7—C12—P1 | 123.4 (5) | C31—C36—C35 | 118.9 (5) |
C7—C12—C11 | 118.3 (6) | C35—C36—P2 | 117.8 (4) |
C11—C12—P1 | 118.2 (5) | S1—C37—H37A | 109.5 |
C14—C13—H13 | 119.7 | S1—C37—H37B | 109.5 |
C14—C13—C18 | 120.7 (6) | S1—C37—H37C | 109.5 |
C18—C13—H13 | 119.7 | H37A—C37—H37B | 109.5 |
C13—C14—H14 | 119.6 | H37A—C37—H37C | 109.5 |
C13—C14—C15 | 120.8 (6) | H37B—C37—H37C | 109.5 |
C15—C14—H14 | 119.6 | S1—C38—H38A | 109.5 |
C14—C15—H15 | 120.1 | S1—C38—H38B | 109.5 |
C14—C15—C16 | 119.9 (6) | S1—C38—H38C | 109.5 |
C16—C15—H15 | 120.1 | H38A—C38—H38B | 109.5 |
C15—C16—H16 | 120.5 | H38A—C38—H38C | 109.5 |
C17—C16—C15 | 119.0 (6) | H38B—C38—H38C | 109.5 |
C17—C16—H16 | 120.5 | O2—N1—O1 | 117.3 (15) |
C16—C17—H17 | 119.4 | O3—N1—O1 | 116 (3) |
C16—C17—C18 | 121.2 (5) | O3—N1—O2 | 125 (3) |
Ag1—P1—C6—C1 | 24.1 (6) | C12—P1—C6—C1 | −109.1 (5) |
Ag1—P1—C6—C5 | −154.1 (5) | C12—P1—C6—C5 | 72.6 (6) |
Ag1—P1—C12—C7 | −141.1 (5) | C12—P1—C18—C13 | 6.2 (5) |
Ag1—P1—C12—C11 | 40.0 (5) | C12—P1—C18—C17 | −178.6 (4) |
Ag1—P1—C18—C13 | −118.9 (4) | C12—C7—C8—C9 | 0.9 (10) |
Ag1—P1—C18—C17 | 56.3 (4) | C13—C14—C15—C16 | 0.1 (10) |
Ag1—P2—C24—C19 | 45.1 (5) | C14—C13—C18—P1 | 175.2 (5) |
Ag1—P2—C24—C23 | −134.8 (4) | C14—C13—C18—C17 | 0.2 (8) |
Ag1—P2—C30—C25 | 27.7 (5) | C14—C15—C16—C17 | −0.8 (9) |
Ag1—P2—C30—C29 | −150.8 (4) | C15—C16—C17—C18 | 1.2 (9) |
Ag1—P2—C36—C31 | −119.3 (4) | C16—C17—C18—P1 | −176.4 (5) |
Ag1—P2—C36—C35 | 57.7 (5) | C16—C17—C18—C13 | −0.9 (8) |
Cl1—Ag1—P1—C6 | 51.4 (2) | C18—P1—C6—C1 | 142.8 (5) |
Cl1—Ag1—P1—C12 | 178.7 (2) | C18—P1—C6—C5 | −35.5 (6) |
Cl1—Ag1—P1—C18 | −65.0 (2) | C18—P1—C12—C7 | 100.6 (5) |
Cl1—Ag1—P2—C24 | −170.54 (18) | C18—P1—C12—C11 | −78.3 (5) |
Cl1—Ag1—P2—C30 | 71.10 (19) | C18—C13—C14—C15 | 0.2 (9) |
Cl1—Ag1—P2—C36 | −51.5 (2) | C19—C20—C21—C22 | 0.1 (9) |
Cl1—Ag1—O4—S1 | 48.0 (4) | C20—C19—C24—P2 | 177.5 (4) |
P1—Ag1—Cl1—Ag1i | −155 (100) | C20—C19—C24—C23 | −2.6 (8) |
P1—Ag1—P2—C24 | 52.6 (2) | C20—C21—C22—C23 | −1.3 (9) |
P1—Ag1—P2—C30 | −65.8 (2) | C21—C22—C23—C24 | 0.5 (8) |
P1—Ag1—P2—C36 | 171.7 (2) | C22—C23—C24—P2 | −178.7 (4) |
P1—Ag1—O4—S1 | 169.9 (3) | C22—C23—C24—C19 | 1.4 (8) |
P2—Ag1—Cl1—Ag1i | 65 (100) | C24—P2—C30—C25 | −94.2 (5) |
P2—Ag1—P1—C6 | 179.4 (2) | C24—P2—C30—C29 | 87.4 (5) |
P2—Ag1—P1—C12 | −53.3 (2) | C24—P2—C36—C31 | 4.6 (5) |
P2—Ag1—P1—C18 | 62.9 (2) | C24—P2—C36—C35 | −178.5 (4) |
P2—Ag1—O4—S1 | −54.2 (4) | C24—C19—C20—C21 | 1.8 (9) |
O4—Ag1—Cl1—Ag1i | −55 (100) | C25—C26—C27—C28 | 0.0 (10) |
O4—Ag1—P1—C6 | −50.1 (3) | C26—C25—C30—P2 | −179.5 (4) |
O4—Ag1—P1—C12 | 77.2 (2) | C26—C25—C30—C29 | −1.0 (8) |
O4—Ag1—P1—C18 | −166.6 (2) | C26—C27—C28—C29 | −0.6 (10) |
O4—Ag1—P2—C24 | −68.6 (2) | C27—C28—C29—C30 | 0.3 (10) |
O4—Ag1—P2—C30 | 173.0 (2) | C28—C29—C30—P2 | 178.9 (5) |
O4—Ag1—P2—C36 | 50.5 (3) | C28—C29—C30—C25 | 0.4 (9) |
C1—C2—C3—C4 | 0.8 (12) | C30—P2—C24—C19 | 167.4 (4) |
C2—C1—C6—P1 | −178.0 (5) | C30—P2—C24—C23 | −12.5 (5) |
C2—C1—C6—C5 | 0.3 (10) | C30—P2—C36—C31 | 114.4 (5) |
C2—C3—C4—C5 | 0.3 (11) | C30—P2—C36—C35 | −68.7 (5) |
C3—C4—C5—C6 | −1.1 (10) | C30—C25—C26—C27 | 0.8 (9) |
C4—C5—C6—P1 | 179.0 (5) | C31—C32—C33—C34 | 0.4 (9) |
C4—C5—C6—C1 | 0.8 (10) | C32—C31—C36—P2 | 177.0 (5) |
C6—P1—C12—C7 | −7.2 (6) | C32—C31—C36—C35 | 0.1 (8) |
C6—P1—C12—C11 | 173.8 (5) | C32—C33—C34—C35 | −0.6 (9) |
C6—P1—C18—C13 | 114.9 (5) | C33—C34—C35—C36 | 0.6 (9) |
C6—P1—C18—C17 | −69.9 (5) | C34—C35—C36—P2 | −177.4 (4) |
C6—C1—C2—C3 | −1.1 (11) | C34—C35—C36—C31 | −0.4 (8) |
C7—C8—C9—C10 | −1.6 (11) | C36—P2—C24—C19 | −83.8 (5) |
C8—C7—C12—P1 | −177.5 (5) | C36—P2—C24—C23 | 96.3 (5) |
C8—C7—C12—C11 | 1.4 (9) | C36—P2—C30—C25 | 158.5 (4) |
C8—C9—C10—C11 | 0.0 (11) | C36—P2—C30—C29 | −20.0 (5) |
C9—C10—C11—C12 | 2.3 (10) | C36—C31—C32—C33 | −0.1 (9) |
C10—C11—C12—P1 | 176.0 (5) | C37—S1—O4—Ag1 | −81.7 (4) |
C10—C11—C12—C7 | −3.0 (9) | C38—S1—O4—Ag1 | 21.0 (5) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O4 | 0.93 | 2.50 | 3.381 (8) | 159 |
C4—H4···O2ii | 0.93 | 2.45 | 3.14 (2) | 131 |
C16—H16···O1iii | 0.93 | 2.24 | 3.00 (2) | 138 |
C37—H37A···O3i | 0.96 | 2.43 | 3.321 (16) | 155 |
C38—H38A···O2i | 0.96 | 2.26 | 3.095 (18) | 145 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O4 | 0.93 | 2.50 | 3.381 (8) | 159 |
C4—H4···O2i | 0.93 | 2.45 | 3.14 (2) | 131 |
C16—H16···O1ii | 0.93 | 2.24 | 3.00 (2) | 138 |
C37—H37A···O3iii | 0.96 | 2.43 | 3.321 (16) | 155 |
C38—H38A···O2iii | 0.96 | 2.26 | 3.095 (18) | 145 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag2Cl(C2H6OS)2(C18H15P)4]NO3 |
Mr | 1518.56 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 12.440 (3), 13.070 (3), 13.579 (3) |
α, β, γ (°) | 93.489 (5), 117.157 (4), 115.354 (4) |
V (Å3) | 1682.6 (7) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.83 |
Crystal size (mm) | 0.3 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Agilent CCD Xcalibur |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2014) |
Tmin, Tmax | 0.861, 0.905 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8521, 5941, 5298 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.153, 1.12 |
No. of reflections | 5868 |
No. of parameters | 430 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.39, −2.12 |
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).
Acknowledgements
This work was supported by the Fundamental Research Funds for the Central Universities (lzujbky-2013–192).
References
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