Di­cyclo­hexyl­ammonium 2,4-di­chloro­phenoxy­acetate and (2,4-di­chloro­phenoxy­acetato-O,O')bis­(tri­phenylphosphine-P)silver(I)

The monoclinic cell of di­cyclo­hexyl­ammonium 2,4-di­chloro­phenoxy­acetate contains four C₁₂H₂₄N⁺·C₅H₈Cl₂O₃^- ion pairs. The ammonium N atom is hydrogen bonded to the oxy­gen ends of two carboxyl groups to form a 12-membered O-C-O...HNH...O-C-O...HNH ring. In (2,4-di­chloro­phenoxy­lacetato)­bis­(tri­phenyl­phosphine)silver(I), [Ag(C₈H₅Cl₂O₃)(C₁₈H₁₅P)₂], the carboxyl CO₂ unit chelates to the Ag atom in an anisobidentate manner [Ag-O = 2.436 (2) and 2.517 (2) Å]; the Ag atom shows distorted tetrahedral geometry.

S1. Comment

Dimeric 2,4-dichlorophenoxyacetic acid [O···O = 2.632 (6) Å; Smith et al., 1976] is a potent herbicide (Que Hee & Sutherland, 1981). The acid cocrystallizes with 4-aminobenzoic acid (Lynch et al., 1992) and with 2-aminopyrimidine (Lynch et al., 1994), and its anion has been characterized as the zinc (Kennard et al., 1982), potassium (Kennard et al., 1983), silver (Mak et al., 1988) and copper (Dendrinou-Samara et al., 1996) salts. The only ammonium salt of the acid that has been examined appears to be the 3-hydroxypyridinium derivative, which adopts a chain structure in which the anions are linked by hydrogen bonds (N···O = 2.60 and O···O = 2.55 Å; Byriel et al., 1992). The study on the present dicyclohexylammonium salt, (I), continues on studies of dicyclohexylammonium salts of monocarboxylic acids. Dicyclohexylammonium trifluoroacetate crystallizes as linear hydrogen-bonded chains [N···O = 2.785 (2) and 2.794 (2) Å; Ng et al., 1999], but this architecture is not common as several other dicyclohexylammonium monocarboxylates pack as dimeric ion-pairs across a centre of symmetry. Such an architecture is observed for the O-(N,N-dimethylmonothiocarbamoyl)acetate [N···O = 2.706 (4) and 2.750 (3) Å], N-phthaloylglycinate [N···O = 2.733 (5) and 2.783 (5) Å; Ng, 1995], bis(N,N-dimethyldithiocarbamoyl)acetate [N···O = 2.701 (3) and 2.796 (3) Å; 2.698 (3) and 2.837 (3) Å; Ng, 1996], N,N-dicyclohexyldithiocarbamoylacetate [N···O = 2.706 (2) and 2.757 (2) Å; Ng, 1997] and 3-oxapentamethylenedithiocarbamoylacetate [N···O = 2.732 (4) and 2.738 (4) Å; Ng & Hook, 1999]. As the substituted acetate group carries bulky substituents, steric effects probably contribute to this type of dimer formation. This arrangment is also found in the 2,4-dichlorophenoxyacetate [N···O = 2.751 (3) and 2.784 (3) Å]. the carbon–oxygen distances in the carboxyl –CO₂ end [C—O = 1.224 (2) and 1.238 (2) Å] indicate delocalization of the negative charge. At the ether linkage, the C_alkyl—O distance [C—O = 1.421 (4) Å] exceeds the C_aryl—O distance [C—O = 1.356 (4) Å]. Bond dimensions in the anion are not much different from those found in the parent acid [C—O_carboxyl = 1.217 (6) and 1.304 (5) Å; C_alkyl—O = 1.423 (5), C_aryl = 1.365 (5) Å; Smith et al., 1976]. In the parent acid as well as in the dicyclohexylammonium salt, the angle at the ether linkage is nearly 120°. The bond dimensions of the ether linkage in the acid and in the salt are in agreement with the results (C_alkyl—O = 1.407, C_aryl—O = 1.371 Å, C—O—C = 119.4°) of molecular mechanics calculations on the monomeric acid computed with the MM3+ basis set (Hypercube Inc., 1995). The computations suggest a planar structure as the most stable conformation; on the other hand, the carboxyl unit is twisted by 85.2° with respect to the aromatic ring in the acid and by 80.8 (3)° in the salt. The synclinal conformation of 2,4-dichlorophenoxyacetic acid appears to be a feature that is not usually found in other phenoxyacetic acids or in metal phenoxyacetates (Mak et al., 1988) such as zinc 2,4-dichlorophenoxyacetate (Kennard et al., 1982) and potassium 2,4-dichlorophenoxyacetate (Kennard et al., 1983).

The silver 2,4-dichlorophenoxyacetate dimer, for which only partial structural details are reported, displays a zigzag motif that is derived through carboxylate bridging of the two independent molecules, and both Ag atoms are two-coordinate. The compound is isomorphous and isostructural with silver 2-methyl-4-chlorophenoxyacetate [Ag—O = 2.185 (3)–2.217 (3) Å], whose full structural details are reported. As the dihedral angles between the carboxyl and the aromatic planes in the latter compound are 15 and 18°, both invidual monomers are almost planar (Mak et al., 1988). Bis(triphenylphosphine)(2,4-dichlorophenoxyacetato)silver, (II), shows a twist [dihedral angle = 65.1 (1)°] that is comparable with that found in the dicyclohexylammonium salt. The chain motif of the silver salt is disrupted upon coordination by the two phosphine-donor ligands, and two weaker silver–oxygen bonds are formed instead [Ag—O = 2.435 (2) and 2.516 (2) Å]. The distorted tetrahedral geometry of silver in this adduct is similar to those found in a number of 1:2 adducts of silver carboxylates with triphenylphosphine such as the acetate (Ng & Othman, 1997), trifluoroacetate (Ng, 1998) and lactate (Hanna & Ng, 2000).

Of the two triphenylphosphine ligands, one is disordered in two of phenyl rings. The C1–C6/C1'–C7' pair of rings are twisted by 42 (1)°, and the C7–C12/C7'–C12' pair by 33 (1)°. The disorder is corroborated by the CP/MAS spectral values: the ¹J(Ag–P) coupling constants of the ordered and disordered phosphorus sites are significantly different. The linewidths of the NMR signals constitute the basis for assigning the ordered/disordered sites; the ordered phosphorus signal yields ¹J(¹⁰⁷Ag–³¹P) and ¹J(¹⁰⁹Ag–³¹P) couplings that are clearly resolved, whereas the disordered phosphorus signal is Lorentzian broaden so that these couplings cannot be resolved. The silver–phosphorus_disordered distance [2.4073 (8) Å] is statistically shorter than the silver–phosphorus_ordered distance [2.4753 (8) Å].

S2. Experimental

Dicyclohexylamine, dissolved in a small volume of ethanol, was added to an ethanol solution of 2,4-dichlorphenoxylacetic acid (1:1 molar ratio of reactants). Ethanol was added to dissolve the ammonium carboxylate that precipitated from solution, and the mixture was heated until most had dissolved completely; the filtered solution afforded long colourless crystals when it was cooled. Solid-state cross-polarization/magic-angle-spinning (CP/MAS) ¹³C NMR: δ = 172.3 (–CO₂); 154.3, 129.8, 114.1 (–C₆H₃Cl₂); 68.0 (–CH₂—O–); 54.6, 51.4, 31.4, 29.8, 28.1, 26.2 p.p.m. (cyclo-C₆H₁₁). Equimolar quantities of aqueous sodium 2,4-dichlorophenoxyacetate and silver nitrate were mixed to afford an immediate white precipitate of silver 2,4-dichlorophenoxyacetate, which was collected, washed with water, and then air dried. The silver salt and triphenylphosphine (1:2 molar ratio) were heated in a small volume of ethanol until the reactants dissolved completely; slow cooling of the filtered solution yielded faint tan-colored crystals of the 1:2 complex. ¹³C NMR: δ = 173.9 (–CO₂); 155.6, 135.4–130.1, 116.4 (–C₆H₃Cl₂ overlapped with –C₆H₅); 70.3 p.p.m. (–CH₂—O). CP/MAS ³¹P NMR for the ordered triphenylphosphine ligand: δ = 20.8±0.1 p.p.m., ¹J(Ag–P) = 508±4 Hz, ²J(P–P) = 140±4 Hz. CP/MAS ³¹P NMR for the disordered triphenylphosphine ligand: δ = 15.9±0.1 p.p.m., ¹J(Ag–P) = 383±4 Hz, ²J(P–P) = 140±4 Hz.

S3. Refinement

In (II), two of the phenyl rings of one of the triphenylphosphine ligands are disordered, and each was refined as two regular hexagons; an ISOR 0.02 instruction was used on all the disordered atoms. The P—C_ipso distances were restrainted by a SADI 0.01 instruction, as were the four P—C_ortho distances.

Computing details

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII (Johnson, 1976) for (II). For both compounds, software used to prepare material for publication: SHELXL97.

(I) Dicyclohexylammonium) 2,4-dichlorophenoxyacetate

Crystal data

C12H24N^+·C8H5O3Cl2^−	F(000) = 856
Mr = 402.34	Dx = 1.260 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3847 (1) Å	Cell parameters from 6107 reflections
b = 18.2966 (3) Å	θ = 2.7–28.4°
c = 8.9780 (1) Å	µ = 0.33 mm^−1
β = 105.296 (1)°	T = 298 K
V = 2120.78 (4) Å^3	Parallelepiped, colourless
Z = 4	0.48 × 0.42 × 0.28 mm

Data collection

Siemens CCD area-detector diffractometer	3737 independent reflections
Radiation source: fine-focus sealed tube	2447 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.7°
w scans	h = −15→15
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −21→11
Tmin = 0.860, Tmax = 0.915	l = −10→10
11531 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.198	w = 1/[σ^2(Fo^2) + (0.0975P)^2 + 0.5146P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3737 reflections	Δρmax = 0.37 e Å^−3
244 parameters	Δρmin = −0.44 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

Special details

Refinement. For both structures, the refinements used only the reflections up to 2θ = 50°.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.4665 (1)	0.4144 (1)	0.3168 (1)	0.124 (1)
Cl2	0.5334 (1)	0.6977 (1)	0.2262 (3)	0.183 (1)
O1	0.0899 (2)	0.4418 (1)	−0.2712 (2)	0.061 (1)
O2	0.1316 (2)	0.4660 (2)	−0.0237 (2)	0.078 (1)
O3	0.3296 (2)	0.4193 (1)	0.0152 (3)	0.070 (1)
N1	−0.0964 (2)	0.5062 (1)	−0.2593 (3)	0.045 (1)
C1	0.1509 (2)	0.4430 (2)	−0.1408 (3)	0.044 (1)
C2	0.2572 (2)	0.4121 (2)	−0.1317 (3)	0.056 (1)
C3	0.3723 (2)	0.4859 (2)	0.0565 (3)	0.060 (1)
C4	0.4422 (2)	0.4910 (3)	0.2021 (4)	0.080 (1)
C5	0.4909 (3)	0.5564 (4)	0.2523 (5)	0.102 (2)
C6	0.4721 (3)	0.6167 (3)	0.1582 (7)	0.105 (2)
C7	0.4038 (3)	0.6123 (2)	0.0156 (5)	0.087 (1)
C8	0.3542 (2)	0.5478 (2)	−0.0341 (4)	0.067 (1)
C9	−0.0977 (2)	0.5778 (2)	−0.3391 (3)	0.045 (1)
C10	−0.0086 (2)	0.6243 (2)	−0.2492 (4)	0.065 (1)
C11	−0.0064 (3)	0.6970 (2)	−0.3291 (5)	0.082 (1)
C12	−0.1074 (3)	0.7380 (2)	−0.3492 (5)	0.083 (1)
C13	−0.1973 (3)	0.6915 (2)	−0.4356 (5)	0.078 (1)
C14	−0.2001 (2)	0.6172 (2)	−0.3606 (4)	0.063 (1)
C15	−0.1766 (2)	0.4509 (2)	−0.3327 (3)	0.045 (1)
C16	−0.1667 (3)	0.3852 (2)	−0.2288 (3)	0.063 (1)
C17	−0.2454 (3)	0.3274 (2)	−0.3016 (4)	0.079 (1)
C18	−0.2369 (3)	0.3051 (2)	−0.4601 (4)	0.069 (1)
C19	−0.2421 (3)	0.3705 (2)	−0.5636 (4)	0.065 (1)
C20	−0.1650 (2)	0.4292 (2)	−0.4898 (3)	0.053 (1)
H1a	−0.031 (3)	0.483 (2)	−0.250 (4)	0.07 (1)*
H1b	−0.102 (3)	0.519 (2)	−0.169 (4)	0.07 (1)*
H2a	0.2500	0.3606	−0.1584	0.084*
H2b	0.2849	0.4364	−0.2081	0.084*
H5	0.5366	0.5596	0.3501	0.152*
H7	0.3910	0.6533	−0.0481	0.131*
H8	0.3073	0.5457	−0.1311	0.101*
H9	−0.0873	0.5685	−0.4415	0.067*
H10a	0.0562	0.5987	−0.2403	0.098*
H10b	−0.0159	0.6326	−0.1459	0.098*
H11a	0.0059	0.6887	−0.4295	0.123*
H11b	0.0502	0.7264	−0.2686	0.123*
H12a	−0.1164	0.7507	−0.2487	0.124*
H12b	−0.1054	0.7829	−0.4059	0.124*
H13a	−0.1925	0.6844	−0.5406	0.118*
H13b	−0.2615	0.7171	−0.4404	0.118*
H14a	−0.2145	0.6236	−0.2610	0.095*
H14b	−0.2552	0.5879	−0.4249	0.095*
H15	−0.2454	0.4725	−0.3454	0.068*
H16a	−0.1773	0.3998	−0.1302	0.094*
H16b	−0.0974	0.3651	−0.2101	0.094*
H17a	−0.2354	0.2847	−0.2352	0.119*
H17b	−0.3145	0.3461	−0.3101	0.119*
H18a	−0.1719	0.2796	−0.4502	0.103*
H18b	−0.2928	0.2717	−0.5064	0.103*
H19a	−0.3114	0.3908	−0.5880	0.097*
H19b	−0.2282	0.3551	−0.6596	0.097*
H20a	−0.0953	0.4113	−0.4793	0.079*
H20b	−0.1754	0.4718	−0.5564	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.061 (1)	0.237 (2)	0.068 (1)	0.031 (1)	0.005 (1)	0.052 (1)
Cl2	0.088 (1)	0.191 (2)	0.270 (2)	−0.043 (1)	0.047 (1)	−0.158 (2)
O1	0.047 (1)	0.090 (2)	0.042 (1)	0.010 (1)	0.005 (1)	−0.004 (1)
O2	0.066 (1)	0.131 (2)	0.043 (1)	0.017 (1)	0.025 (1)	−0.013 (1)
O3	0.045 (1)	0.091 (2)	0.064 ()	0.006 (1)	−0.003 (1)	0.014 (1)
N1	0.044 (1)	0.059 (2)	0.032 (1)	0.006 (1)	0.011 (1)	−0.002 (1)
C1	0.039 (1)	0.055 (2)	0.039 (1)	0.001 (1)	0.013 (1)	−0.000 (1)
C2	0.043 (2)	0.067 (2)	0.057 (2)	0.006 (2)	0.010 (1)	−0.005 (2)
C3	0.034 (1)	0.096 (3)	0.047 (2)	0.005 (2)	0.006 (1)	−0.007 (2)
C4	0.034 (2)	0.155 (4)	0.048 (2)	0.010 (2)	0.008 (1)	−0.011 (2)
C5	0.042 (2)	0.191 (6)	0.071 (3)	−0.004 (3)	0.013 (2)	−0.056 (3)
C6	0.052 (2)	0.142 (4)	0.127 (4)	−0.014 (3)	0.033 (3)	−0.077 (4)
C7	0.058 (2)	0.092 (3)	0.114 (3)	−0.003 (2)	0.027 (2)	−0.033 (3)
C8	0.052 (2)	0.085 (2)	0.060 (2)	0.002 (2)	0.006 (2)	−0.012 (2)
C9	0.046 (2)	0.053 (2)	0.038 (1)	0.000 (1)	0.015 (1)	−0.003 (1)
C10	0.054 (2)	0.067 (2)	0.070 (2)	−0.002 (2)	0.007 (2)	−0.013 (2)
C11	0.070 (2)	0.062 (2)	0.115 (3)	−0.013 (2)	0.027 (2)	−0.015 (2)
C12	0.094 (3)	0.054 (2)	0.104 (3)	0.006 (2)	0.032 (2)	−0.011 (2)
C13	0.075 (2)	0.068 (2)	0.087 (3)	0.012 (2)	0.014 (2)	0.014 (2)
C14	0.050 (2)	0.066 (2)	0.071 (2)	0.007 (2)	0.011 (2)	0.009 (2)
C15	0.038 (1)	0.054 (2)	0.046 (2)	0.004 (1)	0.014 (1)	0.001 (1)
C16	0.090 (2)	0.062 (2)	0.044 (2)	0.000 (2)	0.033 (2)	0.006 (2)
C17	0.103 (3)	0.065 (2)	0.088 (3)	−0.013 (2)	0.056 (2)	0.001 (2)
C18	0.074 (2)	0.062 (2)	0.074 (2)	−0.013 (2)	0.025 (2)	−0.009 (2)
C19	0.060 (2)	0.069 (2)	0.057 (2)	−0.007 (2)	0.001 (2)	−0.004 (2)
C20	0.057 (2)	0.061 (2)	0.037 (2)	−0.008 (2)	0.008 (1)	0.001 (1)

Geometric parameters (Å, º)

Cl1—C4	1.720 (5)	N1—H1b	0.86 (4)
Cl2—C6	1.726 (5)	C2—H2a	0.9700
O1—C1	1.239 (3)	C2—H2b	0.9700
O2—C1	1.222 (3)	C5—H5	0.9300
O3—C3	1.356 (4)	C7—H7	0.9300
O3—C2	1.421 (4)	C8—H8	0.9300
N1—C9	1.491 (4)	C9—H9	0.9800
N1—C15	1.496 (4)	C10—H10a	0.9700
C1—C2	1.514 (4)	C10—H10b	0.9700
C3—C8	1.377 (5)	C11—H11a	0.9700
C3—C4	1.395 (4)	C11—H11b	0.9700
C4—C5	1.380 (7)	C12—H12a	0.9700
C5—C6	1.372 (7)	C12—H12b	0.9700
C6—C7	1.365 (7)	C13—H13a	0.9700
C7—C8	1.371 (5)	C13—H13b	0.9700
C9—C10	1.513 (4)	C14—H14a	0.9700
C9—C14	1.514 (4)	C14—H14b	0.9700
C10—C11	1.515 (5)	C15—H15	0.9800
C11—C12	1.515 (5)	C16—H16a	0.9700
C12—C13	1.511 (5)	C16—H16b	0.9700
C13—C14	1.522 (5)	C17—H17a	0.9700
C15—C16	1.506 (4)	C17—H17b	0.9700
C15—C20	1.512 (4)	C18—H18a	0.9700
C16—C17	1.514 (5)	C18—H18b	0.9700
C17—C18	1.513 (5)	C19—H19a	0.9700
C18—C19	1.506 (5)	C19—H19b	0.9700
C19—C20	1.514 (4)	C20—H20a	0.9700
N1—H1a	0.95 (4)	C20—H20b	0.9700
C3—O3—C2	118.2 (3)	C9—C10—H10a	109.5
C9—N1—C15	117.8 (2)	C11—C10—H10a	109.5
O2—C1—O1	125.7 (3)	C9—C10—H10b	109.5
O2—C1—C2	119.5 (2)	C11—C10—H10b	109.5
O1—C1—C2	114.8 (2)	H10a—C10—H10b	108.1
O3—C2—C1	114.6 (2)	C10—C11—H11a	109.4
O3—C3—C8	125.5 (3)	C12—C11—H11a	109.4
O3—C3—C4	116.6 (4)	C10—C11—H11b	109.4
C8—C3—C4	117.9 (4)	C12—C11—H11b	109.4
C5—C4—C3	120.4 (4)	H11a—C11—H11b	108.0
C5—C4—Cl1	120.8 (3)	C13—C12—H12a	109.6
C3—C4—Cl1	118.7 (4)	C11—C12—H12a	109.6
C6—C5—C4	120.1 (4)	C13—C12—H12b	109.6
C7—C6—C5	119.9 (5)	C11—C12—H12b	109.6
C7—C6—Cl2	121.4 (5)	H12a—C12—H12b	108.1
C5—C6—Cl2	118.7 (4)	C12—C13—H13a	109.1
C6—C7—C8	120.2 (5)	C14—C13—H13a	109.1
C7—C8—C3	121.4 (4)	C12—C13—H13b	109.1
N1—C9—C10	109.3 (2)	C14—C13—H13b	109.1
N1—C9—C14	112.0 (2)	H13a—C13—H13b	107.8
C10—C9—C14	111.1 (2)	C9—C14—H14a	109.5
C9—C10—C11	110.6 (3)	C13—C14—H14a	109.5
C10—C11—C12	111.3 (3)	C9—C14—H14b	109.5
C13—C12—C11	110.3 (3)	C13—C14—H14b	109.5
C12—C13—C14	112.6 (3)	H14a—C14—H14b	108.1
C9—C14—C13	110.7 (3)	N1—C15—H15	108.7
N1—C15—C16	109.3 (2)	C16—C15—H15	108.7
N1—C15—C20	110.5 (2)	C20—C15—H15	108.7
C16—C15—C20	110.8 (2)	C15—C16—H16a	109.5
C15—C16—C17	110.6 (3)	C17—C16—H16a	109.5
C18—C17—C16	112.2 (3)	C15—C16—H16b	109.5
C19—C18—C17	111.3 (3)	C17—C16—H16b	109.5
C18—C19—C20	112.2 (3)	H16a—C16—H16b	108.1
C15—C20—C19	111.6 (2)	C18—C17—H17a	109.2
C9—N1—H1a	109 (2)	C16—C17—H17a	109.2
C15—N1—H1a	106 (2)	C18—C17—H17b	109.2
C9—N1—H1b	103 (2)	C16—C17—H17b	109.2
C15—N1—H1b	111 (2)	H17a—C17—H17b	107.9
H1a—N1—H1b	109 (3)	C19—C18—H18a	109.4
O3—C2—H2a	108.6	C17—C18—H18a	109.4
C1—C2—H2a	108.6	C19—C18—H18b	109.4
O3—C2—H2b	108.6	C17—C18—H18b	109.4
C1—C2—H2b	108.6	H18a—C18—H18b	108.0
H2a—C2—H2b	107.6	C18—C19—H19a	109.2
C6—C5—H5	119.9	C20—C19—H19a	109.2
C4—C5—H5	119.9	C18—C19—H19b	109.2
C6—C7—H7	119.9	C20—C19—H19b	109.2
C8—C7—H7	119.9	H19a—C19—H19b	107.9
C7—C8—H8	119.3	C15—C20—H20a	109.3
C3—C8—H8	119.3	C19—C20—H20a	109.3
N1—C9—H9	108.1	C15—C20—H20b	109.3
C10—C9—H9	108.1	C19—C20—H20b	109.3
C14—C9—H9	108.1	H20a—C20—H20b	108.0
C3—O3—C2—C1	−75.9 (3)	C15—N1—C9—C14	58.4 (3)
O2—C1—C2—O3	−5.7 (4)	N1—C9—C10—C11	178.8 (3)
O1—C1—C2—O3	174.9 (3)	C14—C9—C10—C11	−57.1 (4)
C2—O3—C3—C8	−2.2 (4)	C9—C10—C11—C12	57.7 (4)
C2—O3—C3—C4	179.4 (2)	C10—C11—C12—C13	−55.9 (4)
O3—C3—C4—C5	178.7 (3)	C11—C12—C13—C14	54.4 (5)
C8—C3—C4—C5	0.2 (4)	N1—C9—C14—C13	177.4 (3)
O3—C3—C4—Cl1	−1.1 (4)	C10—C9—C14—C13	54.9 (4)
C8—C3—C4—Cl1	−179.6 (2)	C12—C13—C14—C9	−54.2 (4)
C3—C4—C5—C6	−1.0 (5)	C9—N1—C15—C16	−175.9 (2)
Cl1—C4—C5—C6	178.8 (3)	C9—N1—C15—C20	62.0 (3)
C4—C5—C6—C7	1.0 (6)	N1—C15—C16—C17	−178.7 (2)
C4—C5—C6—Cl2	179.3 (3)	C20—C15—C16—C17	−56.7 (3)
C5—C6—C7—C8	−0.1 (6)	C15—C16—C17—C18	56.0 (4)
Cl2—C6—C7—C8	−178.4 (3)	C16—C17—C18—C19	−53.5 (4)
C6—C7—C8—C3	−0.7 (5)	C17—C18—C19—C20	52.2 (4)
O3—C3—C8—C7	−177.7 (3)	N1—C15—C20—C19	177.3 (2)
C4—C3—C8—C7	0.7 (5)	C16—C15—C20—C19	55.9 (3)
C15—N1—C9—C10	−178.1 (2)	C18—C19—C20—C15	−53.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1a···O1	0.95 (4)	1.85 (4)	2.784 (3)	169 (3)
N1—H1b···O2^i	0.86 (4)	1.90 (4)	2.751 (3)	171 (3)

Symmetry code: (i) −x, −y+1, −z.

(II) Bis(triphenylphosphine)(2,4-dichlorophenoxyacetato)silver(I)

Crystal data

[Ag(C8H5Cl2O3)(C18H15P)2]	F(000) = 1736
Mr = 852.43	Dx = 1.402 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.4500 (2) Å	Cell parameters from 7909 reflections
b = 25.8202 (4) Å	θ = 2.8–28.4°
c = 11.7071 (2) Å	µ = 0.75 mm^−1
β = 96.790 (1)°	T = 298 K
V = 4037.2 (1) Å^3	Parallelepiped, colourless
Z = 4	0.42 × 0.38 × 0.28 mm

Data collection

Siemens CCD area-detector diffractometer	7085 independent reflections
Radiation source: fine-focus sealed tube	5520 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.8°
w scans	h = −15→15
Absorption correction: empirical (SADABS; Sheldrick, 1996)	k = −26→30
Tmin = 0.744, Tmax = 0.818	l = −13→13
22253 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.058P)^2] where P = (Fo^2 + 2Fc^2)/3
7085 reflections	(Δ/σ)max = 0.001
531 parameters	Δρmax = 0.63 e Å^−3
178 restraints	Δρmin = −0.63 e Å^−3

Special details

Refinement. For both structures, the refinements used only the reflections up to 2θ = 50°.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.83691 (2)	0.09632 (1)	0.79029 (2)	0.0473 (1)
Cl1	0.45625 (9)	0.11996 (6)	0.26294 (9)	0.0953 (4)
Cl2	0.3328 (2)	0.25515 (8)	0.56444 (19)	0.172 (1)
P1	1.00941 (6)	0.12158 (3)	0.79246 (7)	0.0433 (2)
P2	0.72360 (6)	0.11832 (4)	0.93503 (7)	0.0422 (2)
O1	0.7450 (2)	0.0265 (1)	0.6853 (2)	0.053 (1)
O2	0.7239 (2)	0.1033 (1)	0.6037 (2)	0.070 (1)
O3	0.5565 (2)	0.0692 (1)	0.4617 (2)	0.057 (1)
C1	1.0225 (4)	0.1920 (1)	0.7855 (6)	0.049 (4)	0.598 (14)
C2	1.1064 (6)	0.2153 (2)	0.7488 (9)	0.105 (4)	0.598 (14)
C3	1.1190 (8)	0.2686 (2)	0.758 (1)	0.145 (6)	0.598 (14)
C4	1.0478 (7)	0.2987 (1)	0.804 (1)	0.147 (6)	0.598 (14)
C5	0.9639 (6)	0.2754 (2)	0.841 (1)	0.122 (5)	0.598 (14)
C6	0.9512 (5)	0.2221 (2)	0.831 (1)	0.087 (4)	0.598 (14)
C1'	1.0130 (8)	0.1911 (2)	0.7926 (7)	0.072 (8)	0.402 (14)
C2'	1.040 (1)	0.2170 (3)	0.6970 (9)	0.111 (6)	0.402 (14)
C3'	1.033 (2)	0.2706 (3)	0.690 (1)	0.159 (9)	0.402 (14)
C4'	0.998 (2)	0.2983 (2)	0.779 (1)	0.16 (1)	0.402 (14)
C5'	0.971 (1)	0.2724 (3)	0.875 (1)	0.16 (1)	0.402 (14)
C6'	0.9782 (9)	0.2188 (3)	0.8816 (9)	0.074 (4)	0.402 (14)
C7	1.0766 (4)	0.0960 (3)	0.6786 (4)	0.055 (5)	0.64 (2)
C8	1.0227 (4)	0.0696 (4)	0.5880 (6)	0.069 (3)	0.64 (2)
C9	1.0709 (6)	0.0514 (5)	0.4973 (5)	0.086 (3)	0.64 (2)
C10	1.1731 (7)	0.0595 (3)	0.4973 (6)	0.092 (5)	0.64 (2)
C11	1.2270 (6)	0.0858 (4)	0.588 (1)	0.095 (4)	0.64 (2)
C12	1.1788 (5)	0.1040 (4)	0.6786 (9)	0.076 (3)	0.64 (2)
C7'	1.0798 (6)	0.1018 (5)	0.6771 (5)	0.047 (7)	0.36 (2)
C8'	1.0316 (7)	0.101 (1)	0.5653 (6)	0.082 (6)	0.36 (2)
C9'	1.0828 (9)	0.084 (1)	0.4755 (7)	0.099 (6)	0.36 (2)
C10'	1.182 (1)	0.0689 (7)	0.497 (1)	0.080 (8)	0.36 (2)
C11'	1.2304 (9)	0.0699 (7)	0.609 (1)	0.070 (5)	0.36 (2)
C12'	1.1792 (7)	0.0863 (6)	0.6990 (7)	0.054 (4)	0.36 (2)
C13	1.0880 (2)	0.1027 (1)	0.9232 (3)	0.038 (1)
C14	1.0915 (3)	0.0511 (2)	0.9536 (4)	0.076 (1)
C15	1.1466 (3)	0.0345 (2)	1.0540 (4)	0.087 (2)
C16	1.1985 (3)	0.0685 (2)	1.1259 (3)	0.066 (1)
C17	1.1980 (3)	0.1193 (2)	1.0964 (4)	0.077 (1)
C18	1.1426 (3)	0.1366 (2)	0.9953 (3)	0.062 (1)
C19	0.5954 (2)	0.0938 (1)	0.9137 (3)	0.048 (1)
C20	0.5796 (3)	0.0441 (2)	0.8705 (3)	0.055 (1)
C21	0.4839 (3)	0.023 (3)	0.8555 (4)	0.073 (1)
C22	0.4049 (3)	0.0517 (2)	0.8832 (4)	0.084 (1)
C23	0.4184 (3)	0.1005 (2)	0.9260 (4)	0.084 (2)
C24	0.5138 (3)	0.1227 (2)	0.9407 (3)	0.065 (1)
C25	0.7103 (2)	0.1882 (1)	0.9414 (3)	0.049 (1)
C26	0.6724 (3)	0.2136 (2)	0.8413 (3)	0.066 (1)
C27	0.6635 (4)	0.2670 (2)	0.8391 (4)	0.083 (1)
C28	0.6950 (4)	0.2956 (2)	0.9353 (5)	0.085 (1)
C29	0.7337 (4)	0.2716 (2)	1.0328 (4)	0.089 (2)
C30	0.7423 (3)	0.2178 (2)	1.0371 (3)	0.072 (1)
C31	0.7682 (2)	0.0984 (1)	1.0818 (3)	0.045 (1)
C32	0.7042 (3)	0.0928 (2)	1.1659 (3)	0.064 (1)
C33	0.7401 (3)	0.0772 (2)	1.2747 (3)	0.077 (1)
C34	0.8397 (3)	0.0662 (2)	1.3024 (4)	0.083 (1)
C35	0.9049 (3)	0.0723 (2)	1.2209 (4)	0.086 (1)
C36	0.8686 (3)	0.0884 (2)	1.1105 (3)	0.068 (1)
C37	0.7001 (2)	0.0578 (2)	0.6166 (3)	0.044 (1)
C38	0.6054 (3)	0.0359 (1)	0.5484 (3)	0.055 (1)
C39	0.5037 (2)	0.1109 (1)	0.4932 (3)	0.050 (1)
C40	0.4522 (3)	0.1390 (2)	0.4033 (3)	0.062 (1)
C41	0.4000 (3)	0.1833 (2)	0.4254 (4)	0.082 (1)
C42	0.3970 (4)	0.1984 (2)	0.5366 (5)	0.093 (2)
C43	0.4450 (3)	0.1709 (2)	0.6270 (4)	0.083 (1)
C44	0.4977 (3)	0.1267 (2)	0.6050 (3)	0.062 (1)
H2	1.1541	0.1951	0.7182	0.158*	0.60 (1)
H3	1.1751	0.2841	0.7335	0.217*	0.60 (1)
H4	1.0562	0.3343	0.8101	0.220*	0.60 (1)
H5	0.9162	0.2955	0.8713	0.183*	0.60 (1)
H6	0.8951	0.2065	0.8559	0.130*	0.60 (1)
H2'	1.0635	0.1985	0.6375	0.167*	0.40 (1)
H3'	1.0508	0.2880	0.6264	0.239*	0.40 (1)
H4'	0.9927	0.3342	0.7749	0.241*	0.40 (1)
H5'	0.9473	0.2910	0.9345	0.236*	0.40 (1)
H6'	0.9600	0.2015	0.9456	0.111*	0.40 (1)
H8	0.9543	0.0642	0.5880	0.103*	0.64 (2)
H9	1.0348	0.0338	0.4367	0.129*	0.64 (2)
H10	1.2054	0.0473	0.4366	0.139*	0.64 (2)
H11	1.2954	0.0912	0.5879	0.142*	0.64 (2)
H12	1.2149	0.1216	0.7392	0.113*	0.64 (2)
H8'	0.9651	0.1112	0.5507	0.124*	0.36 (2)
H9'	1.0505	0.0837	0.4007	0.148*	0.36 (2)
H10'	1.2165	0.0579	0.4373	0.119*	0.36 (2)
H11'	1.2969	0.0596	0.6238	0.105*	0.36 (2)
H12'	1.2115	0.0870	0.7738	0.081*	0.36 (2)
H14	1.0561	0.0270	0.9056	0.114*
H15	1.1480	−0.0006	1.0724	0.131*
H16	1.2340	0.0572	1.1944	0.099*
H17	1.2350	0.1429	1.1441	0.115*
H18	1.1428	0.1716	0.9767	0.093*
H20	0.6336	0.0247	0.8513	0.082*
H21	0.4738	−0.0104	0.8269	0.109*
H22	0.3409	0.0376	0.8727	0.126*
H23	0.3638	0.1192	0.9456	0.127*
H24	0.5228	0.1564	0.9683	0.098*
H26	0.6528	0.1945	0.7751	0.100*
H27	0.6361	0.2835	0.7721	0.125*
H28	0.6897	0.3315	0.9332	0.127*
H29	0.7550	0.2911	1.0979	0.133*
H30	0.7697	0.2017	1.1047	0.108*
H32	0.6363	0.0997	1.1481	0.096*
H33	0.6965	0.0740	1.3304	0.115*
H34	0.8633	0.0547	1.3759	0.125*
H35	0.9728	0.0657	1.2397	0.129*
H36	0.9125	0.0924	1.0555	0.102*
H38a	0.6227	0.0039	0.5121	0.083*
H38b	0.5581	0.0274	0.6021	0.083*
H41	0.3673	0.2026	0.3652	0.123*
H43	0.4423	0.1818	0.7022	0.124*
H44	0.5293	0.1074	0.6659	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0325 (2)	0.0608 (2)	0.0478 (2)	0.0008 (1)	0.0011 (1)	−0.0085 (1)
Cl1	0.0807 (8)	0.147 (1)	0.0527 (6)	0.0326 (8)	−0.0156 (5)	0.0007 (7)
Cl2	0.199 (2)	0.152 (2)	0.164 (2)	0.111 (2)	0.018 (2)	−0.015 (1)
P1	0.0306 (4)	0.0539 (5)	0.0444 (5)	0.0022 (4)	0.0005 (3)	−0.0006 (4)
P2	0.0382 (4)	0.0495 (5)	0.0395 (4)	0.0023 (4)	0.0073 (3)	−0.0020 (4)
O1	0.051 (1)	0.053 (1)	0.052 (1)	0.008 (1)	−0.007 (1)	−0.001 (1)
O2	0.063 (2)	0.059 (2)	0.080 (2)	−0.019 (1)	−0.022 (1)	0.018 (1)
O3	0.049 (1)	0.068 (2)	0.050 (1)	0.005 (1)	−0.008 (1)	−0.001 (1)
C1	0.041 (5)	0.044 (6)	0.063 (8)	0.019 (4)	0.006 (5)	0.015 (6)
C2	0.082 (6)	0.063 (5)	0.18 (1)	0.017 (4)	0.060 (7)	0.049 (6)
C3	0.123 (9)	0.077 (7)	0.25 (1)	0.004 (6)	0.08 (1)	0.052 (8)
C4	0.16 (1)	0.052 (6)	0.23 (1)	0.016 (6)	0.05 (1)	0.046 (8)
C5	0.090 (8)	0.056 (7)	0.23 (1)	0.010 (6)	0.058 (8)	−0.016 (7)
C6	0.048 (5)	0.059 (5)	0.16 (1)	−0.002 (4)	0.024 (7)	−0.021 (5)
C1'	0.07 (1)	0.08 (2)	0.07 (1)	−0.01 (1)	0.01 (1)	0.03 (1)
C2'	0.16 (2)	0.086 (9)	0.094 (9)	0.026 (9)	0.037 (9)	0.053 (8)
C3'	0.23 (2)	0.10 (1)	0.14 (1)	0.00 (1)	0.03 (1)	0.08 (1)
C4'	0.19 (2)	0.11 (1)	0.18 (2)	0.04 (1)	0.01 (2)	0.05 (1)
C5'	0.16 (2)	0.10 (2)	0.21 (2)	0.03 (1)	0.03 (1)	0.01 (1)
C6'	0.052 (7)	0.062 (8)	0.103 (9)	0.004 (5)	−0.012 (7)	−0.012 (6)
C7	0.044 (7)	0.069 (7)	0.054 (8)	0.013 (5)	0.015 (6)	0.003 (5)
C8	0.057 (4)	0.102 (7)	0.044 (4)	0.020 (4)	−0.008 (3)	−0.018 (4)
C9	0.092 (6)	0.115 (8)	0.048 (4)	0.040 (6)	−0.007 (4)	−0.011 (5)
C10	0.11 (1)	0.112 (8)	0.059 (8)	0.047 (7)	0.025 (7)	0.007 (6)
C11	0.082 (7)	0.118 (9)	0.091 (7)	−0.004 (5)	0.040 (6)	−0.015 (7)
C12	0.051 (5)	0.106 (9)	0.073 (5)	−0.013 (4)	0.020 (4)	−0.016 (5)
C7'	0.05 (1)	0.05 (1)	0.04 (1)	−0.010 (8)	−0.022 (8)	−0.002 (7)
C8'	0.059 (7)	0.13 (2)	0.052 (7)	0.025 (8)	−0.004 (6)	−0.007 (8)
C9'	0.10 (1)	0.14 (2)	0.051 (7)	0.01 (1)	−0.004 (7)	−0.019 (9)
C10'	0.06 (1)	0.12 (1)	0.07 (1)	0.00 (1)	0.03 (1)	−0.02 (1)
C11'	0.059 (8)	0.08 (1)	0.077 (9)	0.017 (6)	0.029 (7)	0.004 (8)
C12'	0.055 (7)	0.056 (8)	0.053 (7)	0.012 (5)	0.013 (6)	0.007 (6)
C13	0.033 (2)	0.039 (2)	0.044 (2)	0.001 (1)	0.005 (1)	0.001 (1)
C14	0.079 (3)	0.049 (2)	0.093 (3)	−0.005 (2)	−0.023 (2)	0.004 (2)
C15	0.091 (3)	0.055 (3)	0.109 (4)	0.002 (2)	−0.016 (3)	0.035 (3)
C16	0.060 (2)	0.082 (3)	0.055 (2)	0.018 (2)	−0.001 (2)	0.016 (2)
C17	0.082 (3)	0.076 (3)	0.064 (2)	0.008 (2)	−0.028 (2)	−0.013 (2)
C18	0.065 (2)	0.051 (2)	0.064 (2)	−0.004 (2)	−0.014 (2)	0.001 (2)
C19	0.040 (2)	0.066 (2)	0.038 (2)	0.003 (2)	0.007 (1)	0.004 (2)
C20	0.048 (2)	0.060 (2)	0.056 (2)	−0.004 (2)	0.006 (2)	0.006 (2)
C21	0.063 (3)	0.079 (3)	0.075 (3)	−0.022 (2)	0.005 (2)	0.012 (2)
C22	0.047 (2)	0.116 (4)	0.088 (3)	−0.017 (3)	0.006 (2)	0.018 (3)
C23	0.039 (2)	0.129 (5)	0.087 (3)	0.016 (2)	0.015 (2)	0.002 (3)
C24	0.046 (2)	0.085 (3)	0.065 (2)	0.009 (2)	0.012 (2)	−0.003 (2)
C25	0.046 (2)	0.057 (2)	0.047 (2)	0.006 (2)	0.017 (2)	0.000 (2)
C26	0.074 (3)	0.063 (3)	0.063 (2)	0.010 (2)	0.011 (2)	0.007 (2)
C27	0.095 (3)	0.069 (3)	0.088 (3)	0.020 (3)	0.020 (3)	0.024 (3)
C28	0.115 (4)	0.051 (3)	0.097 (4)	0.016 (3)	0.046 (3)	0.003 (3)
C29	0.137 (4)	0.058 (3)	0.076 (3)	0.000 (3)	0.036 (3)	−0.016 (2)
C30	0.106 (3)	0.058 (3)	0.054 (2)	0.002 (2)	0.017 (2)	−0.008 (2)
C31	0.045 (2)	0.046 (2)	0.044 (2)	−0.001 (1)	0.002 (1)	−0.002 (2)
C32	0.058 (2)	0.085 (3)	0.050 (2)	0.003 (2)	0.010 (2)	0.010 (2)
C33	0.083 (3)	0.097 (3)	0.052 (2)	−0.005 (3)	0.016 (2)	0.013 (2)
C34	0.085 (3)	0.104 (4)	0.056 (3)	−0.011 (3)	−0.009 (2)	0.024 (2)
C35	0.066 (3)	0.126 (4)	0.063 (3)	0.000 (3)	−0.013 (2)	0.018 (3)
C36	0.048 (2)	0.101 (3)	0.055 (2)	−0.001 (2)	0.003 (2)	0.008 (2)
C37	0.042 (2)	0.046 (2)	0.044 (2)	0.002 (2)	0.003 (1)	−0.004 (2)
C38	0.050 (2)	0.049 (2)	0.062 (2)	−0.003 (2)	−0.012 (2)	0.003 (2)
C39	0.034 (2)	0.060 (2)	0.054 (2)	−0.004 (2)	−0.002 (2)	0.006 (2)
C40	0.042 (2)	0.087 (3)	0.054 (2)	0.004 (2)	−0.003 (2)	0.010 (2)
C41	0.072 (3)	0.094 (4)	0.078 (3)	0.023 (3)	0.002 (2)	0.018 (3)
C42	0.086 (3)	0.099 (4)	0.095 (4)	0.036 (3)	0.018 (3)	−0.004 (3)
C43	0.079 (3)	0.096 (4)	0.075 (3)	0.021 (3)	0.013 (2)	−0.006 (3)
C44	0.055 (2)	0.078 (3)	0.052 (2)	0.007 (2)	0.000 (2)	0.006 (2)

Geometric parameters (Å, º)

Ag1—O1	2.435 (2)	C29—C30	1.394 (6)
Ag1—O2	2.516 (2)	C31—C36	1.377 (5)
Ag1—P1	2.4073 (8)	C31—C32	1.390 (5)
Ag1—P2	2.4753 (8)	C32—C33	1.368 (5)
Cl1—C40	1.722 (4)	C33—C34	1.371 (6)
Cl2—C42	1.752 (5)	C34—C35	1.379 (6)
P1—C1'	1.795 (5)	C35—C36	1.390 (6)
P1—C7'	1.812 (4)	C37—C38	1.530 (4)
P1—C7	1.821 (3)	C39—C44	1.382 (5)
P1—C13	1.821 (3)	C39—C40	1.394 (5)
P1—C1	1.830 (3)	C40—C41	1.383 (6)
P2—C25	1.816 (4)	C41—C42	1.363 (6)
P2—C31	1.825 (3)	C42—C43	1.371 (7)
P2—C19	1.826 (3)	C43—C44	1.383 (6)
O1—C37	1.244 (4)	C2—H2	0.9300
O2—C37	1.233 (4)	C3—H3	0.9300
O3—C39	1.365 (4)	C4—H4	0.9300
O3—C38	1.429 (4)	C5—H5	0.9300
C1—C2	1.3900	C6—H6	0.9300
C1—C6	1.3900	C2'—H2'	0.9300
C2—C3	1.3900	C3'—H3'	0.9300
C3—C4	1.3900	C4'—H4'	0.9300
C4—C5	1.3900	C5'—H5'	0.9300
C5—C6	1.3900	C6'—H6'	0.9300
C1'—C2'	1.3900	C8—H8	0.9300
C1'—C6'	1.3900	C9—H9	0.9300
C2'—C3'	1.3900	C10—H10	0.9300
C3'—C4'	1.3900	C11—H11	0.9300
C4'—C5'	1.3900	C12—H12	0.9300
C5'—C6'	1.3900	C8'—H8'	0.9300
C7—C8	1.3900	C9'—H9'	0.9300
C7—C12	1.3900	C10'—H10'	0.9300
C8—C9	1.3900	C11'—H11'	0.9300
C9—C10	1.3900	C12'—H12'	0.9300
C10—C11	1.3900	C14—H14	0.9300
C11—C12	1.3900	C15—H15	0.9300
C7'—C8'	1.3900	C16—H16	0.9300
C7'—C12'	1.3900	C17—H17	0.9300
C8'—C9'	1.3900	C18—H18	0.9300
C9'—C10'	1.3900	C20—H20	0.9300
C10'—C11'	1.3900	C21—H21	0.9300
C11'—C12'	1.3900	C22—H22	0.9300
C13—C18	1.369 (5)	C23—H23	0.9300
C13—C14	1.379 (5)	C24—H24	0.9300
C14—C15	1.382 (6)	C26—H26	0.9300
C15—C16	1.352 (6)	C27—H27	0.9300
C16—C17	1.358 (6)	C28—H28	0.9300
C17—C18	1.395 (5)	C29—H29	0.9300
C19—C20	1.387 (5)	C30—H30	0.9300
C19—C24	1.394 (5)	C32—H32	0.9300
C20—C21	1.389 (5)	C33—H33	0.9300
C21—C22	1.365 (6)	C34—H34	0.9300
C22—C23	1.361 (7)	C35—H35	0.9300
C23—C24	1.397 (6)	C36—H36	0.9300
C25—C30	1.382 (5)	C38—H38a	0.9700
C25—C26	1.385 (5)	C38—H38b	0.9700
C26—C27	1.384 (6)	C41—H41	0.9300
C27—C28	1.371 (7)	C43—H43	0.9300
C28—C29	1.349 (7)	C44—H44	0.9300
O1—Ag1—O2	52.9 (1)	C18—C13—C14	117.4 (3)
O1—Ag1—O1	129.6 (1)	C18—C13—P1	124.2 (3)
O1—Ag1—P2	101.5 (1)	C14—C13—P1	118.3 (3)
O2—Ag1—P1	118.2 (1)	C13—C14—C15	121.2 (4)
O2—Ag1—P2	102.7 (1)	C13—C14—H14	119.4
P1—Ag1—P2	127.0 (1)	C15—C14—H14	119.4
C1—P1—C7	105.6 (3)	C16—C15—C14	120.9 (4)
C1—P1—C7'	100.7 (5)	C16—C15—H15	119.5
C1—P1—C13	104.7 (2)	C14—C15—H15	119.5
C1'—P1—C7'	105.4 (5)	C15—C16—C17	118.9 (4)
C1'—P1—C7	110.4 (3)	C15—C16—H16	120.6
C1'—P1—C13	104.7 (3)	C17—C16—H16	120.6
C7'—P1—C13	104.4 (3)	C16—C17—C18	120.8 (4)
C7—P1—C13	103.2 (2)	C16—C17—H17	119.6
C1—P1—Ag1	111.5 (2)	C18—C17—H17	119.6
C1'—P1—Ag1	107.3 (3)	C13—C18—C17	120.8 (4)
C7—P1—Ag1	117.1 (2)	C13—C18—H18	119.6
C7'—P1—Ag1	120.2 (3)	C17—C18—H18	119.6
C13—P1—Ag1	113.5 (1)	C20—C19—C24	119.2 (3)
C25—P2—C31	105.4 (2)	C20—C19—P2	118.1 (3)
C25—P2—C19	104.7 (2)	C24—C19—P2	122.7 (3)
C31—P2—C19	103.3 (2)	C19—C20—C21	120.5 (4)
C25—P2—Ag1	109.1 (1)	C19—C20—H20	119.7
C31—P2—Ag1	114.8 (1)	C21—C20—H20	119.7
C19—P2—Ag1	118.3 (1)	C22—C21—C20	119.5 (4)
C37—O1—Ag1	91.4 (2)	C22—C21—H21	120.2
C37—O2—Ag1	87.9 (2)	C20—C21—H21	120.2
C39—O3—C38	119.5 (3)	C23—C22—C21	121.1 (4)
C2—C1—C6	120.0	C23—C22—H22	119.4
C2—C1—P1	121.9 (3)	C21—C22—H22	119.4
C6—C1—P1	117.6 (3)	C22—C23—C24	120.3 (4)
C3—C2—C1	120.0	C22—C23—H23	119.8
C3—C2—H2	120.0	C24—C23—H23	119.8
C1—C2—H2	120.0	C19—C24—C23	119.3 (4)
C4—C3—C2	120.0	C19—C24—H24	120.4
C4—C3—H3	120.0	C23—C24—H24	120.4
C2—C3—H3	120.0	C30—C25—C26	118.2 (4)
C3—C4—C5	120.0	C30—C25—P2	124.0 (3)
C3—C4—H4	120.0	C26—C25—P2	117.6 (3)
C5—C4—H4	120.0	C27—C26—C25	120.6 (4)
C6—C5—C4	120.0	C27—C26—H26	119.7
C6—C5—H5	120.0	C25—C26—H26	119.7
C4—C5—H5	120.0	C28—C27—C26	120.3 (4)
C5—C6—C1	120.0	C28—C27—H27	119.9
C5—C6—H6	120.0	C26—C27—H27	119.9
C1—C6—H6	120.0	C29—C28—C27	119.9 (4)
C2'—C1'—C6'	120.0	C29—C28—H28	120.0
C2'—C1'—P1	119.3 (3)	C27—C28—H28	120.0
C6'—C1'—P1	120.3 (4)	C28—C29—C30	120.7 (4)
C1'—C2'—C3'	120.0	C28—C29—H29	119.7
C1'—C2'—H2'	120.0	C30—C29—H29	119.7
C3'—C2'—H2'	120.0	C25—C30—C29	120.3 (4)
C2'—C3'—C4'	120.0	C25—C30—H30	119.9
C2'—C3'—H3'	120.0	C29—C30—H30	119.9
C4'—C3'—H3'	120.0	C36—C31—C32	118.6 (3)
C3'—C4'—C5'	120.0	C36—C31—P2	119.1 (3)
C3'—C4'—H4'	120.0	C32—C31—P2	122.3 (3)
C5'—C4'—H4'	120.0	C33—C32—C31	120.7 (4)
C6'—C5'—C4'	120.0	C33—C32—H32	119.7
C6'—C5'—H5'	120.0	C31—C32—H32	119.7
C4'—C5'—H5'	120.0	C32—C33—C34	120.6 (4)
C5'—C6'—C1'	120.0	C32—C33—H33	119.7
C5'—C6'—H6'	120.0	C34—C33—H33	119.7
C1'—C6'—H6'	120.0	C33—C34—C35	119.7 (4)
C8—C7—C12	120.0	C33—C34—H34	120.1
C8—C7—P1	118.5 (2)	C35—C34—H34	120.1
C12—C7—P1	121.5 (3)	C34—C35—C36	119.8 (4)
C7—C8—C9	120.0	C34—C35—H35	120.1
C7—C8—H8	120.0	C36—C35—H35	120.1
C9—C8—H8	120.0	C31—C36—C35	120.6 (4)
C8—C9—C10	120.0	C31—C36—H36	119.7
C8—C9—H9	120.0	C35—C36—H36	119.7
C10—C9—H9	120.0	O2—C37—O1	125.8 (3)
C11—C10—C9	120.0	O2—C37—C38	120.0 (3)
C11—C10—H10	120.0	O1—C37—C38	114.1 (3)
C9—C10—H10	120.0	O3—C38—C37	115.7 (3)
C10—C11—C12	120.0	O3—C38—H38a	108.4
C10—C11—H11	120.0	C37—C38—H38a	108.4
C12—C11—H11	120.0	O3—C38—H38b	108.4
C11—C12—C7	120.0	C37—C38—H38b	108.4
C11—C12—H12	120.0	H38a—C38—H38b	107.4
C7—C12—H12	120.0	O3—C39—C44	125.4 (3)
C8'—C7'—C12'	120.0	O3—C39—C40	115.8 (3)
C8'—C7'—P1	118.7 (3)	C44—C39—C40	118.8 (4)
C12'—C7'—P1	121.3 (3)	C41—C40—C39	120.5 (4)
C7'—C8'—C9'	120.0	C41—C40—Cl1	119.3 (3)
C7'—C8'—H8'	120.0	C39—C40—Cl1	120.2 (3)
C9'—C8'—H8'	120.0	C42—C41—C40	119.2 (4)
C10'—C9'—C8'	120.0	C42—C41—H41	120.4
C10'—C9'—H9'	120.0	C40—C41—H41	120.4
C8'—C9'—H9'	120.0	C41—C42—C43	121.7 (4)
C9'—C10'—C11'	120.0	C41—C42—Cl2	119.2 (4)
C9'—C10'—H10'	120.0	C43—C42—Cl2	119.1 (4)
C11'—C10'—H10'	120.0	C42—C43—C44	119.2 (4)
C10'—C11'—C12'	120.0	C42—C43—H43	120.4
C10'—C11'—H11'	120.0	C44—C43—H43	120.4
C12'—C11'—H11'	120.0	C39—C44—C43	120.6 (4)
C11'—C12'—C7'	120.0	C39—C44—H44	119.7
C11'—C12'—H12'	120.0	C43—C44—H44	119.7
C7'—C12'—H12'	120.0
O1—Ag1—P1—C1'	140.0 (3)	C7'—C8'—C9'—C10'	0.0
P2—Ag1—P1—C1'	−59.3 (3)	C8'—C9'—C10'—C11'	0.0
O2—Ag1—P1—C1'	76.4 (3)	C9'—C10'—C11'—C12'	0.0
O1—Ag1—P1—C7'	19.7 (5)	C10'—C11'—C12'—C7'	0.0
P2—Ag1—P1—C7'	−179.5 (5)	C8'—C7'—C12'—C11'	0.0
O2—Ag1—P1—C7'	−43.8 (5)	P1—C7'—C12'—C11'	178 (1)
O1—Ag1—P1—C7	15.3 (3)	C1'—P1—C13—C18	−5.3 (4)
P2—Ag1—P1—C7	176.1 (3)	C7'—P1—C13—C18	105.3 (5)
O2—Ag1—P1—C7	−48.2 (3)	C7—P1—C13—C18	110.3 (4)
O1—Ag1—P1—C13	−104.9 (1)	C1—P1—C13—C18	−0.1 (4)
P2—Ag1—P1—C13	55.9 (1)	Ag1—P1—C13—C18	−122.0 (3)
O2—Ag1—P1—C13	−168.4 (1)	C1'—P1—C13—C14	173.2 (4)
O1—Ag1—P1—C1	137.1 (2)	C7'—P1—C13—C14	−76.2 (6)
P2—Ag1—P1—C1	−62.1 (2)	C7—P1—C13—C14	−71.3 (4)
O2—Ag1—P1—C1	73.6 (2)	C1—P1—C13—C14	178.4 (3)
P1—Ag1—P2—C25	60.9 (1)	Ag1—P1—C13—C14	56.5 (3)
O1—Ag1—P2—C25	−134.1 (1)	C18—C13—C14—C15	1.1 (6)
O2—Ag1—P2—C25	−80.0 (1)	P1—C13—C14—C15	−177.5 (4)
P1—Ag1—P2—C31	−57.1 (1)	C13—C14—C15—C16	0.3 (7)
O1—Ag1—P2—C31	107.9 (1)	C14—C15—C16—C17	−1.8 (7)
O2—Ag1—P2—C31	162.1 (1)	C15—C16—C17—C18	1.8 (7)
P1—Ag1—P2—C19	−179.6 (1)	C14—C13—C18—C17	−1.0 (6)
O1—Ag1—P2—C19	−14.6 (1)	P1—C13—C18—C17	177.4 (3)
O2—Ag1—P2—C19	39.5 (2)	C16—C17—C18—C13	−0.4 (7)
P1—Ag1—O1—C37	−105.7 (2)	C25—P2—C19—C20	160.4 (3)
P2—Ag1—O1—C37	89.9 (2)	C31—P2—C19—C20	−89.5 (3)
O2—Ag1—O1—C37	−7.5 (2)	Ag1—P2—C19—C20	38.6 (3)
P1—Ag1—O2—C37	127.6 (2)	C25—P2—C19—C24	−20.6 (3)
O1—Ag1—O2—C37	7.6 (2)	C31—P2—C19—C24	89.5 (3)
P2—Ag1—O2—C37	−87.3 (2)	Ag1—P2—C19—C24	−142.4 (3)
C7'—P1—C1—C2	−30.2 (7)	C24—C19—C20—C21	−0.8 (5)
C7—P1—C1—C2	−30.6 (7)	P2—C19—C20—C21	178.2 (3)
C13—P1—C1—C2	78.0 (7)	C19—C20—C21—C22	0.3 (6)
Ag1—P1—C1—C2	−158.8 (6)	C20—C21—C22—C23	−0.4 (7)
C7'—P1—C1—C6	157.5 (6)	C21—C22—C23—C24	1.1 (7)
C7—P1—C1—C6	157.0 (5)	C20—C19—C24—C23	1.4 (6)
C13—P1—C1—C6	−94.4 (5)	P2—C19—C24—C23	−177.6 (3)
Ag1—P1—C1—C6	28.8 (5)	C22—C23—C24—C19	−1.5 (7)
C6—C1—C2—C3	0.0	C31—P2—C25—C30	8.0 (4)
P1—C1—C2—C3	−172.2 (6)	C19—P2—C25—C30	116.6 (3)
C1—C2—C3—C4	0.0	Ag1—P2—C25—C30	−115.8 (3)
C2—C3—C4—C5	0.0	C31—P2—C25—C26	−177.0 (3)
C3—C4—C5—C6	0.0	C19—P2—C25—C26	−68.3 (3)
C4—C5—C6—C1	0.0	Ag1—P2—C25—C26	59.3 (3)
C2—C1—C6—C5	0.0	C30—C25—C26—C27	−2.4 (6)
P1—C1—C6—C5	172.5 (6)	P2—C25—C26—C27	−177.8 (3)
C7'—P1—C1'—C2'	16.5 (9)	C25—C26—C27—C28	2.0 (7)
C7—P1—C1'—C2'	15.9 (9)	C26—C27—C28—C29	−0.8 (7)
C13—P1—C1'—C2'	126.3 (8)	C27—C28—C29—C30	0.1 (8)
Ag1—P1—C1'—C2'	−112.7 (8)	C26—C25—C30—C29	1.7 (6)
C7'—P1—C1'—C6'	−170.7 (8)	P2—C25—C30—C29	176.8 (3)
C7—P1—C1'—C6'	−171.4 (8)	C28—C29—C30—C25	−0.6 (7)
C13—P1—C1'—C6'	−60.9 (9)	C25—P2—C31—C36	−100.0 (3)
Ag1—P1—C1'—C6'	60.0 (8)	C19—P2—C31—C36	150.4 (3)
C6'—C1'—C2'—C3'	0.0	Ag1—P2—C31—C36	20.1 (3)
P1—C1'—C2'—C3'	172.8 (9)	C25—P2—C31—C32	80.2 (3)
C1'—C2'—C3'—C4'	0.0	C19—P2—C31—C32	−29.5 (3)
C2'—C3'—C4'—C5'	0.0	Ag1—P2—C31—C32	−159.8 (3)
C3'—C4'—C5'—C6'	0.0	C36—C31—C32—C33	−0.6 (6)
C4'—C5'—C6'—C1'	0.0	P2—C31—C32—C33	179.2 (3)
C2'—C1'—C6'—C5'	0.0	C31—C32—C33—C34	−0.7 (7)
P1—C1'—C6'—C5'	−172.7 (9)	C32—C33—C34—C35	1.8 (8)
C1'—P1—C7—C8	−114.0 (7)	C33—C34—C35—C36	−1.5 (8)
C13—P1—C7—C8	134.5 (6)	C32—C31—C36—C35	0.8 (6)
C1—P1—C7—C8	−115.8 (6)	P2—C31—C36—C35	−179.0 (4)
Ag1—P1—C7—C8	9.0 (7)	C34—C35—C36—C31	0.2 (8)
C1'—P1—C7—C12	63.4 (7)	Ag1—O2—C37—O1	−14.7 (4)
C13—P1—C7—C12	−48.1 (7)	Ag1—O2—C37—C38	162.5 (3)
C1—P1—C7—C12	61.6 (6)	Ag1—O1—C37—O2	15.2 (4)
Ag1—P1—C7—C12	−173.6 (6)	Ag1—O1—C37—C38	−162.2 (3)
C12—C7—C8—C9	0.0	C39—O3—C38—C37	−73.9 (4)
P1—C7—C8—C9	177.4 (5)	O2—C37—C38—O3	7.6 (5)
C7—C8—C9—C10	0.0	O1—C37—C38—O3	−174.8 (3)
C8—C9—C10—C11	0.0	C38—O3—C39—C44	4.5 (5)
C9—C10—C11—C12	0.0	C38—O3—C39—C40	−175.3 (3)
C10—C11—C12—C7	0.0	O3—C39—C40—C41	−177.1 (4)
C8—C7—C12—C11	0.0	C44—C39—C40—C41	3.0 (6)
P1—C7—C12—C11	−177.3 (5)	O3—C39—C40—Cl1	0.9 (5)
C1'—P1—C7'—C8'	−83 (1)	C44—C39—C40—Cl1	−179.0 (3)
C13—P1—C7'—C8'	167 (1)	C39—C40—C41—C42	−1.9 (7)
C1—P1—C7'—C8'	−85 (1)	Cl1—C40—C41—C42	−179.9 (4)
Ag1—P1—C7'—C8'	38 (1)	C40—C41—C42—C43	0.4 (8)
C1'—P1—C7'—C12'	99 (1)	C40—C41—C42—Cl2	178.8 (4)
C13—P1—C7'—C12'	−12 (1)	C41—C42—C43—C44	−0.1 (8)
C1—P1—C7'—C12'	97 (1)	Cl2—C42—C43—C44	−178.5 (4)
Ag1—P1—C7'—C12'	−140 (1)	O3—C39—C44—C43	177.4 (4)
C12'—C7'—C8'—C9'	0.0	C40—C39—C44—C43	−2.7 (6)
P1—C7'—C8'—C9'	−178 (1)	C42—C43—C44—C39	1.3 (7)