μ-Chlorido-bis­[(dimethyl sulfoxide-κO)bis­(triphenyl­phosphane-κP)silver(I)] nitrate

Li, Y.-H.; Shao, Y.-L.

doi:10.1107/S2414314616003321

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160332

doi:10.1107/S2414314616003321

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μ-Chlorido-bis[(dimethyl sulfoxide-κO)bis(triphenylphosphane-κP)silver(I)] nitrate

Yun-Hua Li ^a ^* and Yong-Liang Shao ^a

^aCollege of Chemistry and Chemical Engineering, Lanzhou University Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: liyunhua@lzu.edu.cn

Edited by M. Weil, Vienna University of Technology, Austria (Received 8 January 2016; accepted 26 February 2016; online 4 March 2016)

The asymmetric unit of the title salt, [Ag₂Cl(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 Ag^I 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.

Keywords: crystal structure; silver(I); solvent coordination.

CCDC reference: 1455947

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Chemical scheme

Structure description

The Ag^I 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 ).

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 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). Only one orientation of the nitrate anion is shown.

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 refinement 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.

Table 2
Experimental details

Crystal data
Chemical formula	[Ag₂Cl(C₂H₆OS)₂(C₁₈H₁₅P)₄]NO₃
M_r	1518.56
Crystal system, space group	Triclinic, P $[\overline{1}]$
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 )
T_min, T_max	0.861, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	8521, 5941, 5298
R_int	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
Δρ_max, Δρ_min (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 ).

Structural data

CCDC reference: 1455947

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616003321/wm4005sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003321/wm4005Isup2.hkl

checkCIF report

Synthesis and crystallization top

Refinement top

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 U_iso(H) = 1.2U_eq(C) (aromatic H atoms) and 0.96 Å U_iso(H) = 1.5U_eq(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.

Experimental top

Structure description top

The Ag^I 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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: 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).

Figures top

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).

µ-Chlorido-bis[(dimethyl sulfoxide-κO)bis(triphenylphosphane-κP)silver(I)] nitrate top

Crystal data top

[Ag₂Cl(C₂H₆OS)₂(C₁₈H₁₅P)₄]NO₃	Z = 1
M_r = 1518.56	F(000) = 778
Triclinic, P1	D_x = 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

Data collection top

Agilent CCD Xcalibur diffractometer	5941 independent reflections
Radiation source: sealed X-ray tube	5298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −14→14
T_min = 0.861, T_max = 0.905	k = −10→15
8521 measured reflections	l = −16→13

Refinement top

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(F_o²) + (0.0478P)² + 6.8934P] where P = (F_o² + 2F_c²)/3
5868 reflections	(Δ/σ)_max = 0.004
430 parameters	Δρ_max = 2.39 e Å⁻³
6 restraints	Δρ_min = −2.12 e Å⁻³

Crystal data top

[Ag₂Cl(C₂H₆OS)₂(C₁₈H₁₅P)₄]NO₃	γ = 115.354 (4)°
M_r = 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)°

Data collection top

Agilent CCD Xcalibur diffractometer	5941 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	5298 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.905	R_int = 0.062
8521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	6 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.12	Δρ_max = 2.39 e Å⁻³
5868 reflections	Δρ_min = −2.12 e Å⁻³
430 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

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.861, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	8521, 5941, 5298
R_int	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
Δρ_max, Δρ_min (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

Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Bowmaker, G. A., Effendy, Hanna, J. V., Healy, P. C., Skelton, B. W. & White, A. H. (1993). J. Chem. Soc. Dalton Trans. pp. 1387–1397. CSD CrossRef Web of Science Google Scholar
Cassel, A. (1979). Acta Cryst. B35, 174–177. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

μ-Chlorido-bis­­[(di­methyl sulfoxide-κO)bis­­(tri­phenyl­phosphane-κP)silver(I)] nitrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

metal-organic compounds

μ-Chlorido-bis[(dimethyl sulfoxide-κO)bis(triphenylphosphane-κP)silver(I)] nitrate