catena-Poly[[[μ-1,3-bis­(diphenyl­phosphan­yl)propane-κ2P:P′][O-ethyl (4-meth­oxy­phen­yl)phosphono­dithio­ato-κ2S,S′]silver(I)] chloro­form monosolvate]

Sun, D.; Huang, R.-B.

doi:10.1107/S010827011103438X

metal-organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 67| Part 9| September 2011| Pages m315-m317

doi:10.1107/S010827011103438X

catena-Poly[[[μ-1,3-bis(diphenylphosphanyl)propane-κ²P:P′][O-ethyl (4-methoxyphenyl)phosphonodithioato-κ²S,S′]silver(I)] chloroform monosolvate]

Di Sun ^a ^* and Rong-Bin Huang ^b

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bDepartment of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: dsun@sdu.edu.cn

(Received 13 July 2011; accepted 22 August 2011; online 31 August 2011)

Reaction of a mixture of AgOAc, Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithiadiphosphetane-2,4-disulfide] and 1,3-bis(diphenylphosphanyl)propane (dppp) under ultrasonic treatment gave the title compound, {[Ag(C₉H₁₂O₂PS₂)(C₂₇H₂₆P₂)]·CHCl₃}_n, a novel one-dimensional chain based on the in situ-generated bipodal ligand [ArP(OEt)S₂]⁻ (Ar = 4-methoxyphenyl). The compound consists of bidentate bridging 1,3-bis(diphenylphosphanyl)propane (dppp) and in situ-generated bidentate chelating [ArP(OEt)S₂]⁻ ligands. The dppp ligand links the [Ag{ArP(OEt)S₂}] subunit to form an achiral one-dimensional infinite chain. These achiral chains are packed into chiral crystals by virtue of van der Waals interactions. No π–π interactions are observed in the crystal structure.

Comment

The design and construction of coordination structures is one of the most attractive areas of crystal engineering, due to their intriguing structural motifs and functional properties (Chen et al., 2010 ; Blake, Brooks et al., 1999 ; Blake, Champness et al., 1999 ; Evans & Lin, 2002 ; Kitagawa et al., 2004 ; Yaghi et al., 2003 ; Sun et al., 2011 ). Organophosphorus sulfide reagents like P₄S₁₀, Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithiadiphosphetane-2,4-disulfide, LR], and modified LRs such as Davy's reagent, Japanese reagent and Belleau's reagent, have been successfully employed as thionation agents for organic substrates to give thiolactones and thiocarbonyls (Scheibye et al., 1981 ; Jesberger et al., 2003 ; Foreman & Woollins, 2000 ; Ozturk et al., 2007 ). The LR containing a four-membered P₂S₂ ring with alternating P and S atoms can be in equilibrium with a highly reactive dithiophosphine ylide [ArPS₂]⁻ (Ar = 4-methoxyphenyl), which reacts with carbonyl-containing compounds to form P/S-containing anionic ligands. Subsequent assembly of anionic ligands into large Cu^I or Ag^I aggregates has been reported as an efficient synthetic route to a broader variety of coordination polymers or clusters (Shi, Ahlrichs et al., 2005 ). Recently, we used this versatile precursor to construct an Ag₂₀ cluster based on in situ-generated bipodal [ArP(OEt)S₂]⁻ and tripodal [ArPOS₂]²⁻ ligands incorporating the auxiliary Ph₃P (triphenylphosphane) ligand (Sun et al., 2010 ). As an extension of our work, we replaced the auxiliary Ph₃P ligand by the 1,3-bis(diphenylphosphanyl)propane (dppp) ligand and intended to exploit the influence of an auxiliary P-donor on the structures of the AgOAc–LR system. The title compound, (I), was obtained as an infinite chain.

The asymmetric unit of (I) contains one Ag^I cation, one dppp ligand, one anionic [ArP(OEt)S₂]⁻ ligand and one chloroform solvent molecule. As shown in Fig. 1, the Ag^I cation is in a tetrahedral environment, completed by two P atoms from two dppp ligands and two S atoms from one [ArP(OEt)S₂]⁻ ligand, with average Ag—P and Ag—S bond lengths of 2.4500 (11) and 2.6477 (12) Å, respectively. The distortion of the tetrahedron can be indicated by the calculated value of the τ₄ parameter (Yang et al., 2007 ) to describe the geometry of a four-coordinate metal system, which is 0.80 for Ag1 (for perfect tetrahedral geometry, τ₄ = 1). The Ag—P and Ag—S bond lengths (Table 1) are comparable with reported values (Shi et al., 2007 ).

In (I), the [ArP(OEt)S₂]⁻ anion is a bidentate chelating ligand which coordinates one Ag^I centre to form the [Ag{ArP(OEt)S₂}] subunit. The bidentate bridging dppp ligands link the [Ag{ArP(OEt)S₂}] subunits to form an achiral one-dimensional infinite chain along the a axis (Fig. 2). There are no obvious hydrogen-bonding or π-stacking interactions between adjacent chains. Therefore, these achiral chains are packed into chiral crystals by virtue of van der Waals interactions. The chloroform molecules minimize the voids in the crystal structure.

The most fascinating feature of (I) is the in situ-generated anionic [ArP(OEt)S₂]⁻ ligand. In spite of the disassociation of LRs into S²⁻, [ArP(O)S₂]²⁻, [ArS₂P–O–PS₂Ar]²⁻, [ArPS₃]²⁻ and [ArP(O)(OAc)S]⁻ ligands that has been observed (Shi, Shafaei-Fallah et al., 2005 ), it is noteworthy that the generation of the bipodal [ArP(OEt)S₂]⁻ ligand in the course of the reaction between AgOAc and LR is rarely observed. The formation of the bipodal [ArP(OEt)S₂]⁻ anion involves P—S and C—O bond cleavages of LR and acetate, respectively. To the best of our knowledge, the P—O bond is much stronger than the P—S bond, which makes LRs vulnerable to attack by potential nucleophiles, electrophiles and radicals, as demonstrated by Rauchfuss & Zank (1986 ), whereby the LR underwent reversible cleavage to give ArPS₂^. radicals. This could be concluded to be one of the important thermodynamic driving forces behind the formation of the P/S ligand.

Figure 1
The structure of (I)

, showing the atom-numbering scheme and the coordination environment around the Ag^I centre. Displacement ellipsoids are drawn at the 50% probability level. H atoms and the chloroform solvent molecule have been omitted for clarity. [Symmetry code: (i) x + 1, y, z.]

Figure 2
A ball-stick perspective view of the one-dimensional chain in (I)

. H atoms and chloroform solvent molecules have been omitted for clarity.

Experimental

All reagents and solvents were obtained commercially and used without further purification. A mixture of Lawesson's reagent (202 mg, 0.50 mmol), AgOAc (334 mg, 2.00 mmol) and dppp (412 mg, 1.00 mmol) was dissolved in chloroform (10 ml). The mixture was treated under ultrasonic conditions (323 K, 160 W, 40 kHz, 20 min), during which time the solution changed from colourless to yellow. The mixture was filtered and diffusion of diethyl ether into the reaction mixture produced colourless crystals of (I) after two weeks (yield ca 45%, based on AgOAc). Elemental analysis calculated for C₃₇H₃₉AgCl₃O₂P₃S₂: C 50.10, H 4.43%; found: C 49.88, H 4.59%. Selected IR peaks (ν, cm⁻¹): 3064 (w), 2960 (w), 2936 (w), 1588 (s), 1494 (m), 1481 (m), 1436 (s), 1381 (s), 1244 (w), 1177 (m), 1107 (m), 1030 (s), 933 (m), 747 (m), 695 (s), 625 (s), 545 (m).

Crystal data

[Ag(C₉H₁₂O₂PS₂)(C₂₇H₂₆P₂)]·CHCl₃
M_r = 886.93
Monoclinic, P 2₁
a = 7.1493 (14) Å
b = 16.137 (3) Å
c = 17.010 (3) Å
β = 92.95 (3)°
V = 1959.8 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 173 K
0.10 × 0.08 × 0.08 mm

Data collection

Oxford Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.908, T_max = 0.926
26211 measured reflections
7381 independent reflections
6876 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.074
S = 1.01
7381 reflections
433 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.78 e Å⁻³
Absolute structure: Flack (1983 ), with 3390 Friedel pairs
Flack parameter: −0.01 (2)

Table 1
Selected geometric parameters (Å, °)

Ag1—P2ⁱ	2.4424 (11)
Ag1—P1	2.4575 (12)
Ag1—S1	2.6343 (12)
Ag1—S2	2.6610 (12)

P2ⁱ—Ag1—P1	104.67 (4)
P2ⁱ—Ag1—S1	128.23 (4)
P1—Ag1—S1	109.36 (4)
P2ⁱ—Ag1—S2	116.14 (4)
P1—Ag1—S2	119.67 (4)
S1—Ag1—S2	78.33 (4)
Symmetry code: (i) x+1, y, z.

All H atoms were generated geometrically and allowed to ride on their parent atoms in the riding-model approximation, with aromatic C—H = 0.95 Å, methine C—H = 1.00 Å, methylene C—H = 0.99 Å and methyl C—H = 0.98 Å, and with U_iso(H) = 1.2U_eq(C) [1.5U_eq(C) for methyl groups].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S010827011103438X/sf3156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S010827011103438X/sf3156Isup2.hkl

Supporting information file. DOI: 10.1107/S010827011103438X/sf3156Isup4.mol

Comment top

The design and construction of coordination structures is one of the most attractive areas of crystal engineering, due to their intriguing structural motifs and functional properties (Chen et al., 2010; Blake, Brooks et al., 1999; Blake, Champness et al., 1999; Evans & Lin, 2002; Kitagawa et al., 2004; Yaghi et al., 2003; Sun et al., 2011). Organophosphorus sulfide reagents like P₄S₁₀, Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithiadiphosphetane-2,4-disulfide, LR; see first scheme], and modified LRs such as Davy's reagent, Japanese reagent and Belleau's reagent have been successfully employed as thionation agents for organic substrates to give thiolactones and thiocarbonyls (Scheibye et al., 1981; Jesberger et al., 2003; Foreman & Woollins, 2000; Ozturk et al., 2007). The LR containing a four-membered P₂S₂ ring with alternating P and S atoms can be in equilibrium with a highly reactive dithiophosphine ylide [ArPS₂]^- (Ar = 4-methoxyphenyl), which reacts with carbonyl-containing compounds to form P/S-containing anionic ligands. Subsequent assembly of anionic ligands into large Cu^I or Ag^I aggregates has been reported as an efficient synthetic route to a broader variety of coordination polymers or clusters (Shi, Shafaei-Fallah et al., 2005 or Shi, Ahlrichs et al., 2005 ?). Recently, we used this versatile precursor to construct an Ag₂₀ cluster based on in situ-generated bipodal [ArP(OEt)S₂]^- and tripodal [ArPOS₂]^2- ligands incorporating the auxiliary Ph₃P (triphenylphosphane) ligand (Sun et al., 2010). As an extension of our work, we replaced the auxiliary Ph₃P by the 1,3-bis(diphenylphosphanyl)propane (dppp) ligand and intended to exploit the influence of an auxiliary P-donor on the structures of the AgOAc–LR system, and the title compound, (I) (see second scheme), was obtained as an infinite chain.

The asymmetric unit of (I) contains one Ag^I cation, one dppp ligand, one anionic [ArP(OEt)S₂]^- ligand and one solvent chloroform molecule. As shown in Fig. 1, the Ag^I cation is in a tetrahedral environment, completed by two P atoms from two dppp ligands and two S atoms from one [ArP(OEt)S₂]^- ligand, with average Ag—P and Ag—S bond lengths of 2.4500 (11) and 2.6477 (12) Å, respectively. The distortion of the tetrahedron can be indicated by the calculated value of the τ₄ parameter (Yang et al., 2007) to describe the geometry of a four-coordinate metal system, which is 0.80 for Ag1 (for perfect tetrahedral geometry, τ₄ = 1). The Ag—P and Ag—S bond lengths (Table 1) are comparable with reported values (Shi et al., 2007).

In (I), the [ArP(OEt)S₂]^- anion is a bidentate chelating ligand which coordinates one Ag^I centre to form the [Ag(ArP(OEt)S₂)] subunit. The bidentate bridging dppp ligands link the [Ag(ArP(OEt)S₂)] subunits to form an achiral one-diemsnional infinite chain along the a axis (Fig. 2). There are no obvious hydrogen-bonding or π-stacking interactions between adjacent chains. Therefore, these achiral chains are packed into chiral crystals by virtue of van der Waals interactions. The chloroform molecules minimize the voids in the crystal structure.

The most fascinating feature of (I) is the in situ-generated anionic [ArP(OEt)S₂]^- ligand. In spite of the disassociation of LRs into S^2-, [ArP(O)S₂]^2-, [ArS₂P-O-PS₂Ar]^2-, [ArPS₃]^2- and [ArP(O)(OAc)S]^- ligands that has been observed (Shi, Shafaei-Fallah et al., 2005), it is noteworthy that the generation of the bipodal [ArP(OEt)S₂]^- ligand in the course of the reaction between AgOAc and LR is rarely observed. The formation of the bipodal [ArP(OEt)S₂]^- anion involves P—S and C—O bond cleavages of LR and OAc^-, respectively. To the best of our knowledge, the P—O bond is much stronger than the P—S bond, which makes LRs vulnerable to attack by potential nucleophiles, electrophiles and radicals, as demonstrated by Rauchfuss & Zank (1986), whereby the LR underwent reversible cleavage to give ArPS₂^. radicals. This could be concluded to be one of the important thermodynamic driving forces behind the formation of the P/S ligand.

Related literature top

For related literature, see: Blake, Brooks, Champness, Cooke, Deveson, Fenske, Hubberstey, Li & Schröder (1999); Blake, Champness, Hubberstey, Li, Withersby & Schröder (1999); Chen et al. (2010); Evans & Lin (2002); Foreman & Woollins (2000); Jesberger et al. (2003); Kitagawa et al. (2004); Ozturk et al. (2007); Rauchfuss & Zank (1986); Scheibye et al. (1981); Shi et al. (2007); Shi, Ahlrichs, Anson, Rothenberger, Schrodt & Shafaei-Fallah (2005); Shi, Shafaei-Fallah, Matern & Rothenberger (2005); Sun et al. (2010, 2011); Yaghi et al. (2003); Yang et al. (2007).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. A mixture of Lawesson's reagent (202 mg, 0.50 mmol), AgOAc (334 mg, 2.00 mmol) and dppp (412 mg, 1.00 mmol) was dissolved in chloroform (10 ml). The mixture was treated under ultrasonic conditions (323 K, 160 W, 40 KHz, 20 min), during which time the solution changed from colourless to yellow. The mixture was filtered and diffusion of diethyl ether into the reaction mixture produced colourless crystals of (I) after two weeks (yield ca 45% based on AgOAc). Elemental analysis: anal. calc. for AgP₃S₂C₃₇H₃₉O₂Cl₃: C 50.10, H 4.43; found: C 49.88, H 4.59 %. Selected IR peaks (ν, cm^-1): 3064 (w), 2960 (w), 2936 (w), 1588 (s), 1494 (m), 1481 (m), 1436 (s), 1381 (s), 1244 (w), 1177 (m), 1107 (m), 1030 (s), 933 (m), 747 (m), 695 (s), 625 (s), 545 (m).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme and the coordination environment around the Ag^I centre. Displacement ellipsoids are drawn at the 50% probability level. H atoms and the chloroform solvent molecule have been omitted for clarity. [Symmetry code: (i) x + 1, y, z.]
	Fig. 2. A ball-stick perspective view of the one-dimensional chain in (I). H atoms and chloroform solvent molecules have been omitted for clarity.

catena-Poly[[[µ-1,3-bis(diphenylphosphanyl)propane- κ²P:P'][O-ethyl (4-methoxyphenyl)phosphonodithioato- κ²S,S']silver(I)] chloroform monosolvate] top

Crystal data top

[Ag(C₂₇H₂₆P₂)(C₉H₁₂O₂PS₂)]·CHCl₃	F(000) = 904
M_r = 886.93	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 28055 reflections
a = 7.1493 (14) Å	θ = 6.1–55.0°
b = 16.137 (3) Å	µ = 0.98 mm⁻¹
c = 17.010 (3) Å	T = 173 K
β = 92.95 (3)°	Block, colourless
V = 1959.8 (7) Å³	0.10 × 0.08 × 0.08 mm
Z = 2

Data collection top

Oxford Gemini S Ultra diffractometer	7381 independent reflections
Radiation source: sealed tube	6876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 16.1903 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −19→19
T_min = 0.908, T_max = 0.926	l = −20→20
26211 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0103P)² + 2.4402P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
7381 reflections	Δρ_max = 0.64 e Å⁻³
433 parameters	Δρ_min = −0.78 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

Crystal data top

[Ag(C₂₇H₂₆P₂)(C₉H₁₂O₂PS₂)]·CHCl₃	V = 1959.8 (7) Å³
M_r = 886.93	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.1493 (14) Å	µ = 0.98 mm⁻¹
b = 16.137 (3) Å	T = 173 K
c = 17.010 (3) Å	0.10 × 0.08 × 0.08 mm
β = 92.95 (3)°

Data collection top

Oxford Gemini S Ultra diffractometer	7381 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	6876 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.926	R_int = 0.053
26211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.64 e Å⁻³
S = 1.01	Δρ_min = −0.78 e Å⁻³
7381 reflections	Absolute structure: Flack (1983), with how many Friedel pairs?
433 parameters	Absolute structure parameter: −0.01 (2)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ag1	0.93558 (4)	0.267458 (16)	0.277491 (16)	0.03018 (7)
Cl1	−0.1357 (2)	0.19776 (9)	−0.03697 (11)	0.0711 (5)
Cl2	−0.3657 (2)	0.33509 (9)	−0.08913 (8)	0.0602 (4)
Cl3	0.0353 (2)	0.34327 (9)	−0.09900 (8)	0.0585 (3)
S1	1.06916 (17)	0.41944 (7)	0.28743 (6)	0.0378 (3)
S2	0.74536 (17)	0.34191 (7)	0.15887 (6)	0.0373 (3)
P1	0.77758 (15)	0.23400 (6)	0.39844 (6)	0.0252 (2)
P2	0.10029 (15)	0.14039 (6)	0.24491 (6)	0.0251 (2)
P3	0.89644 (17)	0.44060 (6)	0.19358 (6)	0.0324 (2)
C1	0.6657 (6)	0.3153 (2)	0.4529 (2)	0.0291 (9)
C2	0.5576 (7)	0.3740 (3)	0.4110 (3)	0.0393 (11)
H2A	0.5513	0.3729	0.3550	0.047*
C3	0.4599 (8)	0.4336 (3)	0.4498 (3)	0.0495 (13)
H3A	0.3831	0.4721	0.4207	0.059*
C4	0.4735 (8)	0.4375 (3)	0.5301 (3)	0.0508 (13)
H4A	0.4045	0.4782	0.5567	0.061*
C5	0.5867 (8)	0.3827 (3)	0.5729 (3)	0.0505 (13)
H5A	0.6006	0.3875	0.6286	0.061*
C6	0.6790 (7)	0.3214 (3)	0.5347 (2)	0.0408 (11)
H6A	0.7531	0.2826	0.5645	0.049*
C11	0.9449 (6)	0.1878 (3)	0.4702 (2)	0.0291 (8)
C12	0.9285 (7)	0.1090 (3)	0.4999 (3)	0.0499 (13)
H12A	0.8208	0.0769	0.4855	0.060*
C13	1.0680 (8)	0.0754 (4)	0.5510 (3)	0.0633 (16)
H13A	1.0567	0.0203	0.5697	0.076*
C14	1.2194 (8)	0.1217 (4)	0.5739 (3)	0.0555 (14)
H14A	1.3128	0.0994	0.6096	0.067*
C15	1.2378 (7)	0.2005 (4)	0.5454 (3)	0.0571 (15)
H15A	1.3440	0.2327	0.5618	0.069*
C16	1.1040 (6)	0.2336 (3)	0.4934 (3)	0.0411 (11)
H16A	1.1201	0.2878	0.4731	0.049*
C21	0.2016 (6)	0.1364 (2)	0.1496 (2)	0.0277 (8)
C22	0.2914 (6)	0.2072 (3)	0.1246 (2)	0.0369 (10)
H22A	0.2956	0.2549	0.1574	0.044*
C23	0.3751 (7)	0.2099 (3)	0.0527 (3)	0.0427 (11)
H23A	0.4388	0.2582	0.0369	0.051*
C24	0.3638 (6)	0.1407 (3)	0.0048 (3)	0.0422 (11)
H24A	0.4201	0.1418	−0.0445	0.051*
C26	0.1931 (6)	0.0673 (3)	0.1003 (2)	0.0349 (10)
H26A	0.1332	0.0180	0.1163	0.042*
C27	0.2730 (7)	0.0709 (3)	0.0274 (3)	0.0426 (12)
H27A	0.2643	0.0244	−0.0069	0.051*
C31	−0.0589 (5)	0.0526 (2)	0.2446 (2)	0.0265 (8)
C32	−0.2186 (6)	0.0556 (3)	0.1934 (2)	0.0328 (9)
H32A	−0.2370	0.1017	0.1591	0.039*
C33	−0.3494 (7)	−0.0070 (3)	0.1918 (3)	0.0396 (11)
H33A	−0.4560	−0.0041	0.1562	0.047*
C34	−0.3262 (7)	−0.0743 (3)	0.2420 (3)	0.0409 (11)
H34A	−0.4162	−0.1176	0.2408	0.049*
C35	−0.1717 (7)	−0.0778 (3)	0.2935 (3)	0.0417 (11)
H35A	−0.1560	−0.1236	0.3284	0.050*
C36	−0.0380 (6)	−0.0148 (3)	0.2950 (3)	0.0347 (10)
H36A	0.0681	−0.0181	0.3309	0.042*
C41	1.1751 (7)	0.4315 (3)	0.0975 (3)	0.0404 (11)
H41A	1.1344	0.3794	0.0711	0.048*
H41B	1.2597	0.4174	0.1435	0.048*
C42	1.2751 (8)	0.4856 (4)	0.0414 (3)	0.0530 (14)
H42A	1.3846	0.4561	0.0231	0.079*
H42B	1.3159	0.5367	0.0683	0.079*
H42C	1.1902	0.4993	−0.0038	0.079*
C51	0.7469 (6)	0.5282 (3)	0.2090 (2)	0.0325 (9)
C52	0.5653 (7)	0.5178 (3)	0.2302 (2)	0.0358 (10)
H52A	0.5160	0.4633	0.2330	0.043*
C53	0.4509 (7)	0.5847 (3)	0.2476 (2)	0.0372 (10)
H53A	0.3251	0.5760	0.2610	0.045*
C54	0.5245 (6)	0.6645 (3)	0.2449 (2)	0.0362 (10)
C55	0.7067 (7)	0.6760 (3)	0.2225 (3)	0.0420 (11)
H55A	0.7564	0.7304	0.2196	0.050*
C56	0.8154 (7)	0.6092 (3)	0.2046 (3)	0.0417 (11)
H56A	0.9394	0.6181	0.1889	0.050*
C100	0.5942 (6)	0.1550 (3)	0.3855 (2)	0.0280 (9)
H10A	0.6516	0.1025	0.3687	0.034*
H10B	0.5388	0.1449	0.4368	0.034*
C101	0.4398 (6)	0.1793 (2)	0.3256 (2)	0.0289 (9)
H10C	0.4948	0.1912	0.2746	0.035*
H10D	0.3780	0.2304	0.3433	0.035*
C102	0.2939 (5)	0.1103 (2)	0.3145 (2)	0.0277 (8)
H10E	0.2431	0.0968	0.3661	0.033*
H10F	0.3551	0.0599	0.2948	0.033*
C200	0.2363 (7)	0.7284 (3)	0.2725 (3)	0.0508 (13)
H20A	0.1866	0.7826	0.2867	0.076*
H20D	0.2107	0.6881	0.3137	0.076*
H20B	0.1761	0.7102	0.2224	0.076*
C201	−0.1503 (8)	0.3042 (3)	−0.0446 (3)	0.0482 (13)
H20C	−0.1390	0.3283	0.0096	0.058*
O1	1.0128 (4)	0.47708 (19)	0.12311 (17)	0.0389 (7)
O2	0.4314 (5)	0.73445 (19)	0.26493 (19)	0.0460 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03697 (17)	0.02438 (14)	0.02935 (14)	0.00030 (15)	0.00336 (10)	0.00300 (13)
Cl1	0.0694 (11)	0.0505 (9)	0.0944 (12)	0.0067 (7)	0.0130 (8)	0.0195 (8)
Cl2	0.0545 (9)	0.0716 (9)	0.0544 (8)	0.0093 (7)	0.0008 (6)	0.0141 (6)
Cl3	0.0596 (9)	0.0586 (8)	0.0587 (8)	−0.0128 (6)	0.0159 (6)	−0.0031 (6)
S1	0.0480 (7)	0.0292 (6)	0.0345 (6)	−0.0116 (5)	−0.0139 (5)	0.0056 (4)
S2	0.0486 (7)	0.0309 (6)	0.0308 (5)	−0.0058 (5)	−0.0131 (5)	0.0010 (4)
P1	0.0286 (6)	0.0237 (5)	0.0232 (5)	−0.0026 (4)	0.0003 (4)	0.0017 (4)
P2	0.0255 (6)	0.0231 (5)	0.0266 (5)	−0.0001 (4)	0.0002 (4)	−0.0012 (4)
P3	0.0407 (7)	0.0269 (6)	0.0290 (5)	−0.0062 (5)	−0.0058 (4)	0.0056 (4)
C1	0.031 (2)	0.028 (2)	0.028 (2)	−0.0052 (17)	−0.0009 (16)	0.0004 (15)
C2	0.057 (3)	0.026 (2)	0.034 (2)	0.003 (2)	−0.004 (2)	−0.0016 (17)
C3	0.064 (4)	0.031 (3)	0.052 (3)	0.010 (2)	−0.005 (2)	−0.001 (2)
C4	0.062 (4)	0.035 (3)	0.055 (3)	0.013 (2)	0.005 (2)	−0.014 (2)
C5	0.066 (4)	0.051 (3)	0.035 (3)	0.011 (2)	0.004 (2)	−0.009 (2)
C6	0.053 (3)	0.038 (3)	0.031 (2)	0.013 (2)	0.0005 (19)	−0.0012 (18)
C11	0.026 (2)	0.036 (2)	0.025 (2)	−0.0024 (17)	−0.0008 (15)	−0.0031 (16)
C12	0.049 (3)	0.042 (3)	0.056 (3)	−0.010 (2)	−0.018 (2)	0.022 (2)
C13	0.068 (4)	0.057 (4)	0.063 (4)	−0.004 (3)	−0.021 (3)	0.021 (3)
C14	0.054 (4)	0.075 (4)	0.035 (3)	0.019 (3)	−0.015 (2)	0.001 (2)
C15	0.035 (3)	0.082 (4)	0.053 (3)	0.000 (3)	−0.014 (2)	−0.019 (3)
C16	0.031 (3)	0.045 (3)	0.047 (3)	−0.0074 (19)	−0.005 (2)	−0.0025 (19)
C21	0.029 (2)	0.030 (2)	0.0235 (19)	−0.0007 (16)	−0.0025 (15)	0.0043 (15)
C22	0.045 (3)	0.034 (2)	0.032 (2)	−0.0060 (19)	−0.0013 (19)	−0.0003 (17)
C23	0.044 (3)	0.049 (3)	0.035 (2)	−0.008 (2)	0.004 (2)	0.0069 (19)
C24	0.034 (3)	0.061 (3)	0.031 (2)	0.005 (2)	0.0053 (18)	0.005 (2)
C26	0.040 (3)	0.036 (3)	0.029 (2)	0.0003 (19)	−0.0003 (18)	−0.0038 (17)
C27	0.044 (3)	0.050 (3)	0.034 (2)	0.006 (2)	0.004 (2)	−0.012 (2)
C31	0.024 (2)	0.025 (2)	0.030 (2)	0.0009 (15)	0.0017 (15)	−0.0046 (15)
C32	0.029 (2)	0.036 (2)	0.033 (2)	−0.0020 (18)	−0.0014 (17)	−0.0018 (17)
C33	0.028 (3)	0.045 (3)	0.046 (3)	−0.005 (2)	0.001 (2)	−0.010 (2)
C34	0.035 (3)	0.041 (3)	0.047 (3)	−0.014 (2)	0.011 (2)	−0.012 (2)
C35	0.050 (3)	0.031 (2)	0.045 (3)	−0.010 (2)	0.009 (2)	0.0033 (18)
C36	0.033 (3)	0.032 (2)	0.039 (2)	−0.0022 (18)	−0.0016 (18)	0.0014 (17)
C41	0.035 (3)	0.040 (3)	0.046 (3)	0.001 (2)	0.001 (2)	0.000 (2)
C42	0.043 (3)	0.057 (3)	0.059 (3)	0.001 (3)	0.012 (3)	0.004 (3)
C51	0.035 (3)	0.032 (2)	0.030 (2)	−0.0042 (18)	−0.0051 (17)	0.0071 (17)
C52	0.044 (3)	0.029 (2)	0.033 (2)	−0.0117 (19)	−0.0086 (19)	0.0064 (16)
C53	0.038 (3)	0.040 (3)	0.033 (2)	−0.0078 (19)	−0.0054 (18)	0.0033 (18)
C54	0.039 (3)	0.035 (2)	0.033 (2)	−0.0021 (19)	−0.0069 (18)	0.0019 (17)
C55	0.048 (3)	0.028 (2)	0.049 (3)	−0.008 (2)	0.003 (2)	0.0045 (19)
C56	0.042 (3)	0.034 (2)	0.050 (3)	−0.010 (2)	0.004 (2)	0.0049 (19)
C100	0.028 (2)	0.028 (2)	0.028 (2)	−0.0046 (16)	−0.0020 (16)	0.0027 (15)
C101	0.030 (2)	0.027 (2)	0.030 (2)	−0.0026 (16)	−0.0002 (16)	0.0004 (15)
C102	0.025 (2)	0.030 (2)	0.028 (2)	−0.0042 (16)	−0.0005 (15)	−0.0028 (15)
C200	0.043 (3)	0.055 (3)	0.054 (3)	0.002 (2)	0.000 (2)	−0.005 (2)
C201	0.055 (3)	0.055 (3)	0.035 (3)	−0.001 (2)	0.007 (2)	0.006 (2)
O1	0.042 (2)	0.0379 (17)	0.0370 (17)	0.0015 (14)	0.0019 (13)	0.0153 (13)
O2	0.047 (2)	0.0360 (17)	0.055 (2)	0.0019 (14)	−0.0026 (15)	−0.0072 (14)

Geometric parameters (Å, º) top

Ag1—P2ⁱ	2.4424 (11)	C24—H24A	0.9500
Ag1—P1	2.4575 (12)	C26—C27	1.393 (6)
Ag1—S1	2.6343 (12)	C26—H26A	0.9500
Ag1—S2	2.6610 (12)	C27—H27A	0.9500
Cl1—C201	1.725 (5)	C31—C36	1.389 (6)
Cl2—C201	1.753 (6)	C31—C32	1.401 (5)
Cl3—C201	1.773 (5)	C32—C33	1.375 (6)
S1—P3	1.9968 (16)	C32—H32A	0.9500
S2—P3	1.9964 (15)	C33—C34	1.385 (7)
P1—C1	1.815 (4)	C33—H33A	0.9500
P1—C11	1.824 (4)	C34—C35	1.375 (6)
P1—C100	1.834 (4)	C34—H34A	0.9500
P2—C21	1.811 (4)	C35—C36	1.395 (6)
P2—C31	1.818 (4)	C35—H35A	0.9500
P2—C102	1.840 (4)	C36—H36A	0.9500
P2—Ag1ⁱⁱ	2.4424 (11)	C41—O1	1.459 (6)
P3—O1	1.605 (3)	C41—C42	1.502 (7)
P3—C51	1.800 (5)	C41—H41A	0.9900
C1—C6	1.393 (6)	C41—H41B	0.9900
C1—C2	1.396 (6)	C42—H42A	0.9800
C2—C3	1.377 (7)	C42—H42B	0.9800
C2—H2A	0.9500	C42—H42C	0.9800
C3—C4	1.366 (7)	C51—C52	1.376 (6)
C3—H3A	0.9500	C51—C56	1.399 (6)
C4—C5	1.380 (7)	C52—C53	1.395 (6)
C4—H4A	0.9500	C52—H52A	0.9500
C5—C6	1.372 (6)	C53—C54	1.392 (6)
C5—H5A	0.9500	C53—H53A	0.9500
C6—H6A	0.9500	C54—O2	1.363 (5)
C11—C12	1.376 (6)	C54—C55	1.388 (6)
C11—C16	1.396 (6)	C55—C56	1.372 (6)
C12—C13	1.398 (6)	C55—H55A	0.9500
C12—H12A	0.9500	C56—H56A	0.9500
C13—C14	1.355 (8)	C100—C101	1.515 (5)
C13—H13A	0.9500	C100—H10A	0.9900
C14—C15	1.370 (8)	C100—H10B	0.9900
C14—H14A	0.9500	C101—C102	1.531 (5)
C15—C16	1.377 (7)	C101—H10C	0.9900
C15—H15A	0.9500	C101—H10D	0.9900
C16—H16A	0.9500	C102—H10E	0.9900
C21—C22	1.389 (6)	C102—H10F	0.9900
C21—C26	1.394 (5)	C200—O2	1.410 (6)
C22—C23	1.389 (6)	C200—H20A	0.9800
C22—H22A	0.9500	C200—H20D	0.9800
C23—C24	1.381 (7)	C200—H20B	0.9800
C23—H23A	0.9500	C201—H20C	1.0000
C24—C27	1.366 (7)

P2ⁱ—Ag1—P1	104.67 (4)	C36—C31—C32	118.0 (4)
P2ⁱ—Ag1—S1	128.23 (4)	C36—C31—P2	124.2 (3)
P1—Ag1—S1	109.36 (4)	C32—C31—P2	117.7 (3)
P2ⁱ—Ag1—S2	116.14 (4)	C33—C32—C31	121.2 (4)
P1—Ag1—S2	119.67 (4)	C33—C32—H32A	119.4
S1—Ag1—S2	78.33 (4)	C31—C32—H32A	119.4
P3—S1—Ag1	84.30 (5)	C32—C33—C34	120.2 (4)
P3—S2—Ag1	83.59 (5)	C32—C33—H33A	119.9
C1—P1—C11	104.17 (18)	C34—C33—H33A	119.9
C1—P1—C100	103.43 (19)	C35—C34—C33	119.5 (4)
C11—P1—C100	103.66 (18)	C35—C34—H34A	120.3
C1—P1—Ag1	120.16 (13)	C33—C34—H34A	120.3
C11—P1—Ag1	109.63 (14)	C34—C35—C36	120.6 (4)
C100—P1—Ag1	114.16 (13)	C34—C35—H35A	119.7
C21—P2—C31	104.37 (18)	C36—C35—H35A	119.7
C21—P2—C102	104.16 (19)	C31—C36—C35	120.5 (4)
C31—P2—C102	104.26 (18)	C31—C36—H36A	119.7
C21—P2—Ag1ⁱⁱ	116.94 (13)	C35—C36—H36A	119.7
C31—P2—Ag1ⁱⁱ	110.26 (13)	O1—C41—C42	108.0 (4)
C102—P2—Ag1ⁱⁱ	115.54 (13)	O1—C41—H41A	110.1
O1—P3—C51	98.94 (18)	C42—C41—H41A	110.1
O1—P3—S2	111.41 (13)	O1—C41—H41B	110.1
C51—P3—S2	110.69 (15)	C42—C41—H41B	110.1
O1—P3—S1	109.68 (13)	H41A—C41—H41B	108.4
C51—P3—S1	111.41 (14)	C41—C42—H42A	109.5
S2—P3—S1	113.76 (7)	C41—C42—H42B	109.5
C6—C1—C2	118.0 (4)	H42A—C42—H42B	109.5
C6—C1—P1	123.5 (3)	C41—C42—H42C	109.5
C2—C1—P1	118.4 (3)	H42A—C42—H42C	109.5
C3—C2—C1	120.7 (4)	H42B—C42—H42C	109.5
C3—C2—H2A	119.7	C52—C51—C56	117.8 (4)
C1—C2—H2A	119.7	C52—C51—P3	121.2 (3)
C4—C3—C2	120.0 (5)	C56—C51—P3	120.9 (4)
C4—C3—H3A	120.0	C51—C52—C53	122.2 (4)
C2—C3—H3A	120.0	C51—C52—H52A	118.9
C3—C4—C5	120.5 (4)	C53—C52—H52A	118.9
C3—C4—H4A	119.8	C52—C53—C54	118.8 (4)
C5—C4—H4A	119.8	C52—C53—H53A	120.6
C6—C5—C4	119.7 (4)	C54—C53—H53A	120.6
C6—C5—H5A	120.2	O2—C54—C55	115.8 (4)
C4—C5—H5A	120.2	O2—C54—C53	124.6 (4)
C5—C6—C1	121.0 (4)	C55—C54—C53	119.6 (4)
C5—C6—H6A	119.5	C56—C55—C54	120.4 (4)
C1—C6—H6A	119.5	C56—C55—H55A	119.8
C12—C11—C16	118.0 (4)	C54—C55—H55A	119.8
C12—C11—P1	123.9 (3)	C55—C56—C51	121.2 (5)
C16—C11—P1	118.0 (3)	C55—C56—H56A	119.4
C11—C12—C13	121.0 (5)	C51—C56—H56A	119.4
C11—C12—H12A	119.5	C101—C100—P1	113.1 (3)
C13—C12—H12A	119.5	C101—C100—H10A	109.0
C14—C13—C12	119.9 (5)	P1—C100—H10A	109.0
C14—C13—H13A	120.0	C101—C100—H10B	109.0
C12—C13—H13A	120.0	P1—C100—H10B	109.0
C13—C14—C15	120.0 (5)	H10A—C100—H10B	107.8
C13—C14—H14A	120.0	C100—C101—C102	111.2 (3)
C15—C14—H14A	120.0	C100—C101—H10C	109.4
C14—C15—C16	120.7 (5)	C102—C101—H10C	109.4
C14—C15—H15A	119.6	C100—C101—H10D	109.4
C16—C15—H15A	119.6	C102—C101—H10D	109.4
C15—C16—C11	120.4 (5)	H10C—C101—H10D	108.0
C15—C16—H16A	119.8	C101—C102—P2	111.8 (3)
C11—C16—H16A	119.8	C101—C102—H10E	109.2
C22—C21—C26	118.7 (4)	P2—C102—H10E	109.2
C22—C21—P2	117.2 (3)	C101—C102—H10F	109.2
C26—C21—P2	124.1 (3)	P2—C102—H10F	109.2
C21—C22—C23	121.4 (4)	H10E—C102—H10F	107.9
C21—C22—H22A	119.3	O2—C200—H20A	109.5
C23—C22—H22A	119.3	O2—C200—H20D	109.5
C24—C23—C22	118.7 (4)	H20A—C200—H20D	109.5
C24—C23—H23A	120.7	O2—C200—H20B	109.5
C22—C23—H23A	120.7	H20A—C200—H20B	109.5
C27—C24—C23	121.0 (4)	H20D—C200—H20B	109.5
C27—C24—H24A	119.5	Cl1—C201—Cl2	111.4 (3)
C23—C24—H24A	119.5	Cl1—C201—Cl3	110.4 (3)
C27—C26—C21	119.7 (4)	Cl2—C201—Cl3	109.7 (3)
C27—C26—H26A	120.1	Cl1—C201—H20C	108.4
C21—C26—H26A	120.1	Cl2—C201—H20C	108.4
C24—C27—C26	120.4 (4)	Cl3—C201—H20C	108.4
C24—C27—H27A	119.8	C41—O1—P3	119.2 (3)
C26—C27—H27A	119.8	C54—O2—C200	117.6 (4)

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ag(C₂₇H₂₆P₂)(C₉H₁₂O₂PS₂)]·CHCl₃
M_r	886.93
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.1493 (14), 16.137 (3), 17.010 (3)
β (°)	92.95 (3)
V (Å³)	1959.8 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.10 × 0.08 × 0.08

Data collection
Diffractometer	Oxford Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.908, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	26211, 7381, 6876
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.074, 1.01
No. of reflections	7381
No. of parameters	433
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.78
Absolute structure	Flack (1983), with how many Friedel pairs?
Absolute structure parameter	−0.01 (2)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008) and SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Ag1—P2ⁱ	2.4424 (11)	Ag1—S1	2.6343 (12)
Ag1—P1	2.4575 (12)	Ag1—S2	2.6610 (12)

P2ⁱ—Ag1—P1	104.67 (4)	P2ⁱ—Ag1—S2	116.14 (4)
P2ⁱ—Ag1—S1	128.23 (4)	P1—Ag1—S2	119.67 (4)
P1—Ag1—S1	109.36 (4)	S1—Ag1—S2	78.33 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 21021061 and 21071118) and Shandong University.

References

Blake, A. J., Brooks, N. R., Champness, N. R., Cooke, P. A., Deveson, A. M., Fenske, D., Hubberstey, P., Li, W. S. & Schröder, M. (1999). J. Chem. Soc. Dalton Trans. pp. 2103–2110. Web of Science CSD CrossRef Google Scholar
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ISSN: 2053-2296

Volume 67| Part 9| September 2011| Pages m315-m317

doi:10.1107/S010827011103438X

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