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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m264.
Published online 2007 December 21. doi:  10.1107/S1600536807067013
PMCID: PMC2915175

Bis[μ-methyl­enebis(diphenyl­phosphine)]bis­[(5-nitro-1,10-phenanthroline)silver(I)] bis­(hexa­fluoridoanti­monate)

Abstract

In the title compound, [Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2, the two AgI atoms are bridged by the two methyl­enebis(diphenyl­phosphine) ligands and an eight-membered centrosymmetric metallacyclic ring is formed. The metal atom exhibits a distorted tetra­hedral coordination geometry, coordinated by two P atoms of the bridging ligands and two N atoms of the chelating 5-nitro-1,10-phenanthroline ligand. The latter ligand shows minor disorder, adopting two orientations with site occupancy factors of 0.84 and 0.16.

Related literature

For related literature, see: Ho & Bau (1983 [triangle]); Smith & Cagle (1947 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m264-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2
  • M r = 1906.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m264-efi1.jpg
  • a = 12.8034 (7) Å
  • b = 23.3993 (10) Å
  • c = 13.5580 (11) Å
  • β = 117.936 (2)°
  • V = 3588.5 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.46 mm−1
  • T = 293 (2) K
  • 0.35 × 0.35 × 0.28 mm

Data collection

  • Rigaku Mercury 70 CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 [triangle]) T min = 0.816, T max = 1.000 (expected range = 0.543–0.665)
  • 22441 measured reflections
  • 6301 independent reflections
  • 5851 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.060
  • S = 1.11
  • 6301 reflections
  • 623 parameters
  • 486 restraints
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.70 e Å−3

Data collection: CrystalClear (Rigaku, 2000 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1999 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067013/gk2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067013/gk2121Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound, [Ag2(methylenebis(diphenylphosphine))2(5-nitro-1,10-phenanthroline)2]. (SbF6)2, is formed by self-assembly between the metal diphosphine compound [Ag2(methylenebis(diphenylphosphine))2](SbF6)2 and 5-nitro-1,10-phenanthroline. In the crystal structure, the complex cation exists as a centrosymmetric dimer. Perspective view of the title compound is given in Fig. 1. The two methylenebis(diphenylphosphine) molecules bridge two Ag(5-nitro-1,10-phenanthroline) moieties to form an eight-membered Ag2P4C2 metallacyclic ring with the 5-nitro-1,10-phenanthroline ligand chelating Ag atoms. The P1—Ag—P2 angle of 144.11 (3)° is much larger than the N1—Ag—N2 angle of 68.59 (10)°, indicating a distorted tetrahedral coordination geometry around the silver atom.

Experimental

[Ag2(methylenebis(diphenylphosphine))2](SbF6)2 (Ho & Bau,1983) and 5-nitro-1,10-phenanthroline (Smith & Cagle, 1947) were prepared according to the literature procedures. The title compound was prepared by reacting 0.25 mmol of [Ag2(bis(diphenylphosphino)2](SbF6)2 with 0.5 mmol 5-nitro-1,10-phenanthroline in 15 ml CH3CN at room temperature for 1 h. The resulting mixture was evaporated to dryness using Schlenk techniques. The solid product was recrystallized from a mixture of 15 ml CH2Cl2 and 10 ml CH3OH giving yellow crystals suitable for X-ray analysis.

Refinement

All H atoms were included in calculated positions with C—H = 0.93 Å to 0.97 Å with Uiso(H) = 1.2Ueq(C). Large anisotropic displacement parameters of the phenathroline ligand and two high residual peaks in a diffence map indicated a possible disorder of this ligand with the residual peaks attributed to a second position of the nitro group. The disorder of the 5-nitro-1,10-phenanthroline fragment was resolved into two partial-occupancy orientations and the occupancy factors were refined at 0.842 (4) and 0.158 (4). The atoms from the disordered unit were refined with the 'SIMU 0.01' restraint.

Figures

Fig. 1.
ORTEP view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level and all hydrogen atoms were omitted for clarity. Atoms with the suffix A were generated by the symmetery operation -x, -y, ...
Fig. 2.
Crystal packing of the title compound

Crystal data

[Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2F000 = 1880
Mr = 1906.38Dx = 1.764 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7865 reflections
a = 12.8034 (7) Åθ = 3.0–25.0º
b = 23.3993 (10) ŵ = 1.46 mm1
c = 13.5580 (11) ÅT = 293 (2) K
β = 117.936 (2)ºPrism, yellow
V = 3588.5 (4) Å30.35 × 0.35 × 0.28 mm
Z = 2

Data collection

Rigaku Mercury 70 CCD diffractometer6301 independent reflections
Radiation source: fine-focus sealed tube5851 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
Detector resolution: 14.6306 pixels mm-1θmax = 25.0º
T = 293(2) Kθmin = 3.0º
ω scansh = −15→15
Absorption correction: multi-scan(CrystalClear; Rigaku, 2000)k = −27→26
Tmin = 0.816, Tmax = 1.000l = −16→15
22441 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.060  w = 1/[σ2(Fo2) + (0.0186P)2 + 5.1P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.002
6301 reflectionsΔρmax = 0.66 e Å3
623 parametersΔρmin = −0.70 e Å3
486 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. 2007–03-05 # Formatted by publCIF
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)

xyzUiso*/UeqOcc. (<1)
Ag0.023652 (17)−0.075515 (9)1.091671 (17)0.01867 (6)
P1−0.17901 (6)−0.06326 (3)0.94206 (6)0.01775 (16)
P20.19380 (6)−0.02588 (3)1.22857 (6)0.01697 (15)
C21−0.2634 (2)−0.00996 (12)0.9721 (2)0.0216 (6)
C22−0.3864 (3)−0.00586 (13)0.9110 (3)0.0247 (7)
H22A−0.4286−0.03250.85550.030*
C23−0.4457 (3)0.03785 (14)0.9330 (3)0.0326 (8)
H23A−0.52740.04090.89130.039*
C24−0.3838 (3)0.07685 (15)1.0167 (3)0.0401 (9)
H24A−0.42410.10591.03150.048*
C25−0.2625 (3)0.07299 (15)1.0786 (3)0.0385 (8)
H25A−0.22110.09921.13510.046*
C26−0.2027 (3)0.02995 (13)1.0562 (3)0.0280 (7)
H26A−0.12090.02761.09770.034*
C31−0.2520 (2)−0.13177 (12)0.9320 (2)0.0205 (6)
C32−0.2280 (2)−0.17707 (13)0.8787 (2)0.0253 (7)
H32A−0.1866−0.17030.83890.030*
C33−0.2651 (3)−0.23201 (13)0.8845 (3)0.0313 (8)
H33A−0.2483−0.26200.84910.038*
C34−0.3271 (3)−0.24197 (14)0.9432 (3)0.0357 (8)
H34A−0.3513−0.27890.94800.043*
C35−0.3532 (3)−0.19762 (15)0.9945 (3)0.0351 (8)
H35A−0.3960−0.20461.03290.042*
C36−0.3163 (2)−0.14242 (14)0.9894 (3)0.0274 (7)
H36A−0.3343−0.11261.02420.033*
C410.1816 (2)−0.02647 (12)1.3574 (2)0.0200 (6)
C420.2094 (3)−0.07752 (14)1.4183 (3)0.0275 (7)
H42A0.2376−0.10851.39480.033*
C430.1952 (3)−0.08225 (15)1.5130 (3)0.0330 (8)
H43A0.2131−0.11651.55250.040*
C440.1546 (3)−0.03626 (16)1.5490 (3)0.0353 (8)
H44A0.1466−0.03931.61350.042*
C450.1261 (3)0.01406 (15)1.4896 (3)0.0352 (8)
H45A0.09830.04491.51380.042*
C460.1388 (3)0.01893 (13)1.3932 (3)0.0261 (7)
H46A0.11850.05291.35280.031*
C510.3399 (2)−0.05683 (13)1.2753 (2)0.0206 (6)
C520.3518 (3)−0.10922 (13)1.2338 (3)0.0283 (7)
H52A0.2852−0.12811.18080.034*
C530.4631 (3)−0.13370 (15)1.2712 (3)0.0389 (9)
H53A0.4709−0.16881.24300.047*
C540.5617 (3)−0.10585 (16)1.3500 (3)0.0371 (8)
H54A0.6360−0.12231.37510.044*
C550.5510 (3)−0.05397 (16)1.3916 (3)0.0349 (8)
H55A0.6182−0.03521.44390.042*
C560.4403 (2)−0.02935 (14)1.3558 (3)0.0262 (7)
H56A0.43320.00541.38560.031*
C61−0.2118 (2)−0.04967 (12)0.7965 (2)0.0206 (6)
H61A−0.1595−0.07260.77910.025*
H61B−0.2924−0.06130.74690.025*
C10.0907 (6)−0.1990 (2)1.0194 (7)0.0286 (12)0.842 (4)
H1A0.1206−0.17480.98430.034*0.842 (4)
C20.0947 (6)−0.2583 (2)1.0054 (5)0.0438 (16)0.842 (4)
H2A0.1270−0.27290.96190.053*0.842 (4)
C30.0510 (5)−0.2940 (2)1.0557 (5)0.0445 (16)0.842 (4)
H3A0.0541−0.33321.04710.053*0.842 (4)
C40.0010 (5)−0.2723 (2)1.1206 (4)0.0338 (12)0.842 (4)
C5−0.0497 (5)−0.3045 (2)1.1798 (5)0.0424 (17)0.842 (4)
C6−0.1018 (4)−0.2802 (2)1.2341 (4)0.0427 (13)0.842 (4)
H6A−0.1364−0.30331.26660.051*0.842 (4)
C7−0.1057 (5)−0.2198 (2)1.2435 (4)0.0323 (12)0.842 (4)
C8−0.1592 (4)−0.1931 (2)1.3008 (4)0.0411 (12)0.842 (4)
H8A−0.1969−0.21461.33240.049*0.842 (4)
C9−0.1552 (5)−0.1351 (2)1.3094 (4)0.0417 (12)0.842 (4)
H9A−0.1903−0.11651.34680.050*0.842 (4)
C10−0.0977 (5)−0.1041 (2)1.2612 (5)0.0326 (13)0.842 (4)
H10A−0.0943−0.06461.26900.039*0.842 (4)
C11−0.0517 (5)−0.18563 (19)1.1947 (5)0.0235 (10)0.842 (4)
C120.0005 (7)−0.2113 (2)1.1323 (5)0.0251 (11)0.842 (4)
N10.0456 (9)−0.1765 (2)1.0812 (9)0.0238 (10)0.842 (4)
N2−0.0478 (8)−0.12770 (18)1.2050 (7)0.0233 (10)0.842 (4)
N3−0.0420 (4)−0.36777 (18)1.1863 (4)0.0676 (16)0.842 (4)
O1−0.0046 (4)−0.39241 (17)1.1320 (6)0.121 (3)0.842 (4)
O2−0.0729 (8)−0.3919 (2)1.2455 (8)0.095 (3)0.842 (4)
C1'0.110 (4)−0.1903 (13)1.011 (4)0.023 (3)0.158 (4)
H1'A0.1420−0.16280.98420.027*0.158 (4)
C2'0.116 (3)−0.2481 (13)0.987 (3)0.027 (4)0.158 (4)
H2'A0.1480−0.25850.94050.032*0.158 (4)
C3'0.075 (3)−0.2885 (12)1.031 (3)0.028 (4)0.158 (4)
H3'A0.0816−0.32691.01730.034*0.158 (4)
C4'0.023 (3)−0.2733 (11)1.098 (3)0.024 (3)0.158 (4)
C5'−0.026 (2)−0.3121 (10)1.149 (2)0.026 (4)0.158 (4)
H5'A−0.0234−0.35111.13720.031*0.158 (4)
C6'−0.074 (3)−0.2941 (10)1.210 (3)0.032 (4)0.158 (4)
C7'−0.086 (3)−0.2346 (9)1.228 (3)0.026 (3)0.158 (4)
C8'−0.129 (2)−0.2136 (10)1.299 (2)0.031 (4)0.158 (4)
H8'A−0.1587−0.23901.33180.037*0.158 (4)
C9'−0.127 (3)−0.1569 (10)1.320 (2)0.031 (3)0.158 (4)
H9'A−0.1576−0.14331.36560.038*0.158 (4)
C10'−0.079 (3)−0.1187 (11)1.271 (3)0.031 (3)0.158 (4)
H10B−0.0756−0.07981.28620.037*0.158 (4)
C11'−0.034 (3)−0.1943 (10)1.185 (3)0.025 (3)0.158 (4)
C12'0.012 (4)−0.2131 (11)1.114 (3)0.022 (3)0.158 (4)
N1'0.059 (6)−0.1739 (13)1.072 (5)0.020 (3)0.158 (4)
N2'−0.038 (5)−0.1379 (11)1.204 (4)0.023 (3)0.158 (4)
N3'−0.1201 (15)−0.3401 (8)1.2576 (16)0.040 (3)0.158 (4)
O2'−0.1967 (14)−0.3283 (7)1.2810 (14)0.049 (3)0.158 (4)
O1'−0.091 (4)−0.3889 (11)1.259 (4)0.033 (3)0.158 (4)
Sb0.035784 (19)0.195912 (9)1.342401 (19)0.03131 (7)
F1−0.0552 (2)0.15895 (13)1.3963 (3)0.0868 (9)
F2−0.09810 (19)0.23510 (10)1.2379 (2)0.0632 (7)
F30.12724 (18)0.23192 (9)1.28696 (18)0.0447 (5)
F40.0682 (2)0.25534 (10)1.4442 (2)0.0624 (7)
F50.0064 (2)0.13675 (9)1.23847 (18)0.0559 (6)
F60.16940 (18)0.15634 (9)1.44683 (17)0.0461 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag0.01518 (11)0.01797 (12)0.02097 (11)−0.00183 (8)0.00690 (9)−0.00001 (9)
P10.0148 (3)0.0175 (4)0.0195 (4)−0.0012 (3)0.0069 (3)0.0020 (3)
P20.0140 (3)0.0155 (4)0.0193 (4)−0.0006 (3)0.0060 (3)0.0015 (3)
C210.0220 (14)0.0207 (16)0.0236 (15)0.0009 (12)0.0119 (13)0.0042 (12)
C220.0219 (15)0.0260 (17)0.0288 (16)−0.0009 (13)0.0141 (13)0.0049 (13)
C230.0249 (16)0.037 (2)0.041 (2)0.0085 (15)0.0203 (15)0.0085 (16)
C240.044 (2)0.034 (2)0.054 (2)0.0089 (17)0.0326 (19)−0.0018 (18)
C250.0392 (19)0.035 (2)0.045 (2)−0.0055 (16)0.0229 (17)−0.0149 (17)
C260.0250 (15)0.0286 (17)0.0316 (17)−0.0025 (14)0.0142 (14)−0.0036 (14)
C310.0122 (13)0.0225 (16)0.0190 (14)−0.0032 (12)0.0007 (11)0.0047 (12)
C320.0190 (14)0.0256 (17)0.0229 (16)−0.0019 (13)0.0027 (13)0.0019 (13)
C330.0229 (16)0.0212 (17)0.0294 (17)−0.0023 (13)−0.0048 (14)0.0023 (14)
C340.0225 (16)0.0249 (18)0.0349 (19)−0.0070 (14)−0.0071 (15)0.0109 (15)
C350.0212 (16)0.043 (2)0.0323 (18)−0.0082 (15)0.0050 (14)0.0169 (16)
C360.0175 (14)0.0321 (18)0.0274 (16)−0.0026 (13)0.0062 (13)0.0065 (14)
C410.0125 (13)0.0241 (16)0.0199 (14)−0.0032 (12)0.0047 (12)0.0002 (12)
C420.0230 (15)0.0291 (18)0.0303 (17)0.0016 (13)0.0125 (14)0.0067 (14)
C430.0233 (16)0.043 (2)0.0299 (17)−0.0013 (15)0.0099 (14)0.0136 (16)
C440.0332 (18)0.052 (2)0.0255 (17)−0.0073 (17)0.0174 (15)0.0033 (16)
C450.0382 (19)0.038 (2)0.0373 (19)−0.0051 (16)0.0239 (16)−0.0075 (16)
C460.0263 (16)0.0243 (17)0.0310 (17)−0.0030 (13)0.0161 (14)0.0007 (13)
C510.0165 (13)0.0235 (16)0.0209 (15)0.0007 (12)0.0080 (12)0.0062 (12)
C520.0208 (15)0.0215 (17)0.0403 (19)−0.0008 (13)0.0124 (14)−0.0002 (14)
C530.0352 (19)0.0238 (18)0.061 (2)0.0089 (15)0.0247 (18)0.0045 (17)
C540.0205 (16)0.043 (2)0.047 (2)0.0121 (15)0.0152 (16)0.0166 (17)
C550.0158 (15)0.048 (2)0.0332 (18)−0.0019 (15)0.0055 (14)0.0064 (16)
C560.0196 (15)0.0296 (18)0.0288 (16)−0.0015 (13)0.0108 (13)−0.0024 (14)
C610.0222 (14)0.0162 (15)0.0237 (15)−0.0003 (12)0.0111 (13)0.0000 (12)
C10.026 (3)0.029 (3)0.026 (2)0.005 (2)0.0082 (18)−0.001 (2)
C20.047 (3)0.035 (3)0.039 (3)0.012 (3)0.011 (2)−0.007 (3)
C30.047 (3)0.021 (2)0.038 (3)0.011 (2)−0.002 (2)−0.006 (2)
C40.028 (3)0.0185 (19)0.028 (3)0.0031 (17)−0.0086 (17)0.0019 (18)
C50.035 (3)0.017 (2)0.037 (4)−0.007 (2)−0.015 (2)0.014 (2)
C60.033 (2)0.039 (3)0.032 (2)−0.013 (2)−0.0048 (18)0.017 (2)
C70.026 (2)0.040 (3)0.018 (2)−0.014 (2)0.0001 (17)0.007 (2)
C80.034 (3)0.064 (4)0.024 (2)−0.023 (2)0.0132 (19)0.002 (2)
C90.037 (3)0.060 (3)0.033 (2)−0.018 (2)0.020 (2)−0.011 (2)
C100.030 (3)0.042 (3)0.029 (2)−0.012 (2)0.017 (2)−0.011 (2)
C110.016 (2)0.028 (2)0.0144 (18)−0.0046 (17)−0.0025 (14)0.0035 (17)
C120.020 (2)0.0213 (18)0.020 (3)−0.0026 (16)−0.0031 (16)0.0098 (17)
N10.019 (3)0.0228 (18)0.022 (3)0.0015 (16)0.0032 (14)−0.0027 (16)
N20.022 (2)0.025 (2)0.0200 (16)−0.008 (2)0.0071 (15)−0.002 (2)
N30.038 (2)0.026 (2)0.081 (3)−0.008 (2)−0.020 (2)0.018 (2)
O10.086 (3)0.023 (2)0.269 (8)0.004 (2)0.097 (4)0.008 (3)
O20.114 (7)0.034 (3)0.066 (5)−0.031 (3)−0.016 (3)0.030 (3)
C1'0.024 (5)0.024 (5)0.023 (5)0.004 (5)0.014 (4)−0.001 (4)
C2'0.029 (6)0.025 (6)0.029 (5)0.001 (5)0.016 (5)0.001 (5)
C3'0.033 (6)0.023 (5)0.030 (6)0.007 (5)0.016 (5)−0.004 (5)
C4'0.023 (5)0.020 (4)0.023 (5)0.001 (4)0.007 (4)0.003 (4)
C5'0.024 (5)0.019 (5)0.025 (6)−0.004 (5)0.003 (5)0.007 (5)
C6'0.028 (5)0.028 (5)0.029 (5)−0.007 (5)0.004 (5)0.010 (5)
C7'0.021 (4)0.032 (5)0.019 (4)−0.006 (4)0.004 (4)0.003 (4)
C8'0.025 (5)0.039 (6)0.023 (5)−0.011 (5)0.007 (5)0.000 (5)
C9'0.028 (5)0.046 (5)0.025 (4)−0.012 (5)0.016 (4)−0.005 (5)
C10'0.028 (5)0.037 (5)0.026 (4)−0.012 (5)0.012 (4)−0.003 (5)
C11'0.021 (4)0.022 (4)0.019 (4)−0.010 (4)−0.001 (4)0.005 (4)
C12'0.019 (4)0.022 (4)0.019 (5)0.002 (4)0.004 (4)−0.001 (4)
N1'0.020 (5)0.022 (4)0.019 (5)−0.005 (4)0.009 (4)0.006 (4)
N2'0.022 (5)0.033 (5)0.017 (4)−0.008 (5)0.010 (4)−0.002 (5)
N3'0.040 (5)0.039 (5)0.043 (5)−0.007 (5)0.021 (4)0.018 (5)
O2'0.045 (6)0.043 (6)0.053 (6)−0.007 (5)0.019 (5)0.020 (5)
O1'0.039 (5)0.038 (6)0.036 (6)−0.006 (5)0.030 (5)0.015 (5)
Sb0.03320 (12)0.02695 (13)0.03999 (14)0.00654 (9)0.02232 (11)0.00912 (10)
F10.0786 (18)0.091 (2)0.119 (2)−0.0047 (16)0.0694 (19)0.0431 (19)
F20.0377 (12)0.0606 (16)0.0893 (18)0.0241 (11)0.0282 (13)0.0301 (14)
F30.0464 (12)0.0476 (13)0.0557 (13)0.0058 (10)0.0370 (11)0.0089 (10)
F40.0965 (19)0.0479 (14)0.0622 (15)0.0149 (13)0.0533 (15)−0.0061 (12)
F50.0565 (14)0.0377 (12)0.0437 (13)0.0067 (11)−0.0013 (11)−0.0024 (10)
F60.0489 (12)0.0339 (11)0.0392 (12)0.0060 (10)0.0070 (10)0.0053 (9)

Geometric parameters (Å, °)

Ag—N12.392 (6)C1—N11.329 (5)
Ag—P22.3982 (7)C1—C21.404 (6)
Ag—N1'2.38 (3)C1—H1A0.9300
Ag—N2'2.49 (3)C2—C31.353 (7)
Ag—P12.4491 (7)C2—H2A0.9300
Ag—N22.451 (5)C3—C41.403 (7)
P1—C211.817 (3)C3—H3A0.9300
P1—C311.828 (3)C4—C121.437 (5)
P1—C611.843 (3)C4—C51.457 (8)
P2—C511.821 (3)C5—C61.330 (7)
P2—C411.825 (3)C5—N31.483 (6)
P2—C61i1.835 (3)C6—C71.424 (7)
C21—C261.395 (4)C6—H6A0.9300
C21—C221.398 (4)C7—C81.400 (7)
C22—C231.387 (4)C7—C111.408 (5)
C22—H22A0.9300C8—C91.359 (7)
C23—C241.381 (5)C8—H8A0.9300
C23—H23A0.9300C9—C101.395 (6)
C24—C251.380 (5)C9—H9A0.9300
C24—H24A0.9300C10—N21.322 (5)
C25—C261.383 (4)C10—H10A0.9300
C25—H25A0.9300C11—N21.361 (5)
C26—H26A0.9300C11—C121.432 (6)
C31—C361.395 (4)C12—N11.361 (5)
C31—C321.396 (4)N3—O21.191 (8)
C32—C331.385 (4)N3—O11.198 (7)
C32—H32A0.9300C1'—N1'1.325 (17)
C33—C341.382 (5)C1'—C2'1.405 (17)
C33—H33A0.9300C1'—H1'A0.9300
C34—C351.376 (5)C2'—C3'1.350 (18)
C34—H34A0.9300C2'—H2'A0.9300
C35—C361.388 (4)C3'—C4'1.397 (17)
C35—H35A0.9300C3'—H3'A0.9300
C36—H36A0.9300C4'—C12'1.440 (16)
C41—C461.383 (4)C4'—C5'1.447 (17)
C41—C421.400 (4)C5'—C6'1.322 (19)
C42—C431.384 (4)C5'—H5'A0.9300
C42—H42A0.9300C6'—C7'1.435 (18)
C43—C441.379 (5)C6'—N3'1.50 (3)
C43—H43A0.9300C7'—C8'1.387 (17)
C44—C451.376 (5)C7'—C11'1.429 (16)
C44—H44A0.9300C8'—C9'1.357 (18)
C45—C461.396 (4)C8'—H8'A0.9300
C45—H45A0.9300C9'—C10'1.417 (17)
C46—H46A0.9300C9'—H9'A0.9300
C51—C521.386 (4)C10'—N2'1.324 (17)
C51—C561.394 (4)C10'—H10B0.9300
C52—C531.392 (4)C11'—N2'1.349 (16)
C52—H52A0.9300C11'—C12'1.420 (16)
C53—C541.376 (5)C12'—N1'1.354 (16)
C53—H53A0.9300N3'—O2'1.197 (16)
C54—C551.372 (5)N3'—O1'1.197 (19)
C54—H54A0.9300Sb—F11.853 (2)
C55—C561.390 (4)Sb—F31.8630 (19)
C55—H55A0.9300Sb—F41.864 (2)
C56—H56A0.9300Sb—F21.874 (2)
C61—P2i1.835 (3)Sb—F61.8759 (19)
C61—H61A0.9700Sb—F51.883 (2)
C61—H61B0.9700
N1—Ag—P2115.8 (3)N1—C1—C2122.1 (5)
N1—Ag—N1'6.2 (7)N1—C1—H1A119.0
P2—Ag—N1'113.8 (17)C2—C1—H1A119.0
N1—Ag—N2'62.3 (6)C3—C2—C1119.4 (5)
P2—Ag—N2'104.1 (13)C3—C2—H2A120.3
N1'—Ag—N2'68.3 (7)C1—C2—H2A120.3
N1—Ag—P1100.1 (3)C2—C3—C4120.7 (4)
P2—Ag—P1144.11 (3)C2—C3—H3A119.6
N1'—Ag—P1101.7 (17)C4—C3—H3A119.6
N2'—Ag—P193.4 (14)C3—C4—C12117.1 (4)
N1—Ag—N268.51 (15)C3—C4—C5127.6 (4)
P2—Ag—N2103.1 (2)C12—C4—C5115.2 (5)
N1'—Ag—N274.5 (6)C6—C5—C4123.5 (4)
N2'—Ag—N26.3 (7)C6—C5—N3115.5 (6)
P1—Ag—N290.9 (2)C4—C5—N3121.0 (6)
C21—P1—C31106.38 (13)C5—C6—C7121.5 (5)
C21—P1—C61105.11 (13)C5—C6—H6A119.2
C31—P1—C61102.66 (13)C7—C6—H6A119.2
C21—P1—Ag113.91 (10)C8—C7—C11118.9 (4)
C31—P1—Ag105.39 (9)C8—C7—C6122.7 (4)
C61—P1—Ag121.90 (9)C11—C7—C6118.4 (5)
C51—P2—C41101.49 (13)C9—C8—C7118.9 (4)
C51—P2—C61i104.48 (13)C9—C8—H8A120.5
C41—P2—C61i104.99 (13)C7—C8—H8A120.5
C51—P2—Ag119.29 (10)C8—C9—C10119.0 (5)
C41—P2—Ag106.43 (9)C8—C9—H9A120.5
C61i—P2—Ag118.08 (10)C10—C9—H9A120.5
C26—C21—C22118.7 (3)N2—C10—C9123.8 (5)
C26—C21—P1118.7 (2)N2—C10—H10A118.1
C22—C21—P1122.5 (2)C9—C10—H10A118.1
C23—C22—C21120.1 (3)N2—C11—C7121.3 (4)
C23—C22—H22A119.9N2—C11—C12118.2 (4)
C21—C22—H22A119.9C7—C11—C12120.5 (4)
C24—C23—C22120.2 (3)N1—C12—C4120.8 (5)
C24—C23—H23A119.9N1—C12—C11118.5 (4)
C22—C23—H23A119.9C4—C12—C11120.7 (4)
C25—C24—C23120.4 (3)C1—N1—C12119.8 (4)
C25—C24—H24A119.8C1—N1—Ag121.8 (4)
C23—C24—H24A119.8C12—N1—Ag118.1 (3)
C24—C25—C26119.7 (3)C10—N2—C11118.0 (4)
C24—C25—H25A120.1C10—N2—Ag125.2 (3)
C26—C25—H25A120.1C11—N2—Ag116.0 (3)
C25—C26—C21120.9 (3)O2—N3—O1122.8 (6)
C25—C26—H26A119.5O2—N3—C5118.7 (7)
C21—C26—H26A119.5O1—N3—C5118.6 (6)
C36—C31—C32118.9 (3)N1'—C1'—C2'122 (2)
C36—C31—P1122.0 (2)N1'—C1'—H1'A119.1
C32—C31—P1118.4 (2)C2'—C1'—H1'A119.1
C33—C32—C31120.7 (3)C3'—C2'—C1'119 (2)
C33—C32—H32A119.6C3'—C2'—H2'A120.3
C31—C32—H32A119.6C1'—C2'—H2'A120.3
C34—C33—C32119.6 (3)C2'—C3'—C4'120.9 (19)
C34—C33—H33A120.2C2'—C3'—H3'A119.6
C32—C33—H33A120.2C4'—C3'—H3'A119.6
C35—C34—C33120.4 (3)C3'—C4'—C12'117.0 (16)
C35—C34—H34A119.8C3'—C4'—C5'126.3 (18)
C33—C34—H34A119.8C12'—C4'—C5'116.6 (16)
C34—C35—C36120.5 (3)C6'—C5'—C4'123 (2)
C34—C35—H35A119.8C6'—C5'—H5'A118.7
C36—C35—H35A119.8C4'—C5'—H5'A118.7
C35—C36—C31119.9 (3)C5'—C6'—C7'122 (2)
C35—C36—H36A120.1C5'—C6'—N3'115.7 (19)
C31—C36—H36A120.1C7'—C6'—N3'121.9 (18)
C46—C41—C42118.8 (3)C8'—C7'—C6'124.6 (17)
C46—C41—P2123.7 (2)C8'—C7'—C11'117.2 (16)
C42—C41—P2117.3 (2)C6'—C7'—C11'117.6 (17)
C43—C42—C41120.5 (3)C9'—C8'—C7'121.4 (18)
C43—C42—H42A119.7C9'—C8'—H8'A119.3
C41—C42—H42A119.7C7'—C8'—H8'A119.3
C44—C43—C42120.0 (3)C8'—C9'—C10'118.9 (18)
C44—C43—H43A120.0C8'—C9'—H9'A120.5
C42—C43—H43A120.0C10'—C9'—H9'A120.5
C45—C44—C43120.1 (3)N2'—C10'—C9'121 (2)
C45—C44—H44A119.9N2'—C10'—H10B119.7
C43—C44—H44A119.9C9'—C10'—H10B119.7
C44—C45—C46120.2 (3)N2'—C11'—C7'120.3 (17)
C44—C45—H45A119.9N2'—C11'—C12'119.5 (16)
C46—C45—H45A119.9C7'—C11'—C12'120.0 (17)
C41—C46—C45120.3 (3)N1'—C12'—C4'120.5 (17)
C41—C46—H46A119.8N1'—C12'—C11'118.7 (17)
C45—C46—H46A119.8C4'—C12'—C11'120.3 (17)
C52—C51—C56119.3 (3)C1'—N1'—C12'120 (2)
C52—C51—P2120.1 (2)C1'—N1'—Ag121.4 (17)
C56—C51—P2120.6 (2)C12'—N1'—Ag117.8 (15)
C51—C52—C53120.3 (3)C10'—N2'—C11'121.4 (19)
C51—C52—H52A119.9C10'—N2'—Ag124.1 (16)
C53—C52—H52A119.9C11'—N2'—Ag114.3 (14)
C54—C53—C52119.8 (3)O2'—N3'—O1'120.1 (19)
C54—C53—H53A120.1O2'—N3'—C6'118.5 (18)
C52—C53—H53A120.1O1'—N3'—C6'121 (2)
C55—C54—C53120.4 (3)F1—Sb—F3179.02 (13)
C55—C54—H54A119.8F1—Sb—F491.09 (13)
C53—C54—H54A119.8F3—Sb—F489.86 (10)
C54—C55—C56120.3 (3)F1—Sb—F290.32 (12)
C54—C55—H55A119.8F3—Sb—F289.92 (10)
C56—C55—H55A119.8F4—Sb—F290.14 (12)
C55—C56—C51119.8 (3)F1—Sb—F689.50 (11)
C55—C56—H56A120.1F3—Sb—F690.25 (9)
C51—C56—H56A120.1F4—Sb—F690.09 (10)
P2i—C61—P1112.26 (15)F2—Sb—F6179.72 (11)
P2i—C61—H61A109.2F1—Sb—F590.56 (14)
P1—C61—H61A109.2F3—Sb—F588.49 (10)
P2i—C61—H61B109.2F4—Sb—F5178.33 (11)
P1—C61—H61B109.2F2—Sb—F590.13 (11)
H61A—C61—H61B107.9F6—Sb—F589.65 (9)
N1—Ag—P1—C21143.06 (17)C61i—P2—C51—C5646.3 (3)
P2—Ag—P1—C21−39.37 (11)Ag—P2—C51—C56−179.1 (2)
N1'—Ag—P1—C21149.1 (6)C56—C51—C52—C53−0.9 (5)
N2'—Ag—P1—C2180.6 (6)P2—C51—C52—C53−178.5 (3)
N2—Ag—P1—C2174.73 (15)C51—C52—C53—C540.3 (5)
N1—Ag—P1—C3126.83 (17)C52—C53—C54—C55−0.3 (5)
P2—Ag—P1—C31−155.60 (10)C53—C54—C55—C561.0 (5)
N1'—Ag—P1—C3132.9 (6)C54—C55—C56—C51−1.6 (5)
N2'—Ag—P1—C31−35.7 (6)C52—C51—C56—C551.6 (4)
N2—Ag—P1—C31−41.50 (15)P2—C51—C56—C55179.2 (2)
N1—Ag—P1—C61−89.21 (17)C21—P1—C61—P2i49.57 (18)
P2—Ag—P1—C6188.35 (12)C31—P1—C61—P2i160.67 (15)
N1'—Ag—P1—C61−83.2 (6)Ag—P1—C61—P2i−81.92 (16)
N2'—Ag—P1—C61−151.7 (6)C2—C1—N1—Ag−174.5 (6)
N2—Ag—P1—C61−157.54 (15)C4—C12—N1—Ag174.2 (5)
N1—Ag—P2—C5124.36 (19)C11—C12—N1—Ag−3.4 (11)
N1'—Ag—P2—C5117.9 (7)P2—Ag—N1—C1−85.9 (8)
N2'—Ag—P2—C5190.1 (8)N1'—Ag—N1—C1−14 (18)
P1—Ag—P2—C51−152.97 (11)N2'—Ag—N1—C1−178.9 (18)
N2—Ag—P2—C5196.58 (17)P1—Ag—N1—C192.5 (8)
N1—Ag—P2—C41−89.44 (18)N2—Ag—N1—C1179.5 (9)
N1'—Ag—P2—C41−95.8 (7)P2—Ag—N1—C12100.1 (7)
N2'—Ag—P2—C41−23.7 (8)N1'—Ag—N1—C12172 (19)
P1—Ag—P2—C4193.23 (11)N2'—Ag—N1—C127.1 (17)
N2—Ag—P2—C41−17.21 (16)P1—Ag—N1—C12−81.5 (8)
N1—Ag—P2—C61i152.98 (18)N2—Ag—N1—C125.5 (7)
N1'—Ag—P2—C61i146.6 (7)C9—C10—N2—C11−0.7 (11)
N2'—Ag—P2—C61i−141.2 (8)C9—C10—N2—Ag168.8 (5)
P1—Ag—P2—C61i−24.35 (12)C7—C11—N2—C10−0.9 (11)
N2—Ag—P2—C61i−134.79 (17)C12—C11—N2—C10178.9 (7)
C31—P1—C21—C26133.8 (2)C7—C11—N2—Ag−171.3 (5)
C61—P1—C21—C26−117.8 (2)C12—C11—N2—Ag8.5 (9)
Ag—P1—C21—C2618.2 (3)N1—Ag—N2—C10−176.9 (8)
C31—P1—C21—C22−49.0 (3)P2—Ag—N2—C1070.2 (7)
C61—P1—C21—C2259.4 (3)N1'—Ag—N2—C10−178.3 (19)
Ag—P1—C21—C22−164.7 (2)N2'—Ag—N2—C10170 (15)
C26—C21—C22—C231.1 (4)P1—Ag—N2—C10−76.4 (7)
P1—C21—C22—C23−176.0 (2)N1—Ag—N2—C11−7.2 (6)
C21—C22—C23—C24−1.2 (5)P2—Ag—N2—C11−120.1 (6)
C22—C23—C24—C250.5 (5)N1'—Ag—N2—C11−8.7 (18)
C23—C24—C25—C260.3 (6)N2'—Ag—N2—C11−20 (14)
C24—C25—C26—C21−0.4 (5)P1—Ag—N2—C1193.2 (6)
C22—C21—C26—C25−0.3 (5)C6—C5—N3—O2−6.1 (8)
P1—C21—C26—C25176.9 (3)C4—C5—N3—O2171.9 (7)
C21—P1—C31—C36−27.8 (3)C6—C5—N3—O1174.2 (5)
C61—P1—C31—C36−138.0 (2)C4—C5—N3—O1−7.8 (7)
Ag—P1—C31—C3693.5 (2)N1—Ag—N1'—C1'169 (23)
C21—P1—C31—C32161.8 (2)P2—Ag—N1'—C1'−81 (5)
C61—P1—C31—C3251.7 (2)N2'—Ag—N1'—C1'−177 (5)
Ag—P1—C31—C32−76.9 (2)P1—Ag—N1'—C1'94 (5)
C36—C31—C32—C33−1.3 (4)N2—Ag—N1'—C1'−179 (5)
P1—C31—C32—C33169.4 (2)N1—Ag—N1'—C12'−3(15)
C31—C32—C33—C340.3 (4)P2—Ag—N1'—C12'107 (4)
C32—C33—C34—C350.8 (4)N2'—Ag—N1'—C12'10 (4)
C33—C34—C35—C36−0.9 (5)P1—Ag—N1'—C12'−79 (5)
C34—C35—C36—C31−0.1 (4)N2—Ag—N1'—C12'9(4)
C32—C31—C36—C351.2 (4)C9'—C10'—N2'—C11'−4(7)
P1—C31—C36—C35−169.2 (2)C9'—C10'—N2'—Ag171 (3)
C51—P2—C41—C46135.8 (2)C7'—C11'—N2'—C10'6(7)
C61i—P2—C41—C4627.2 (3)C12'—C11'—N2'—C10'−179 (5)
Ag—P2—C41—C46−98.7 (2)C7'—C11'—N2'—Ag−169 (3)
C51—P2—C41—C42−48.9 (2)C12'—C11'—N2'—Ag6(6)
C61i—P2—C41—C42−157.5 (2)N1—Ag—N2'—C10'178 (5)
Ag—P2—C41—C4276.5 (2)P2—Ag—N2'—C10'66 (4)
C46—C41—C42—C43−0.5 (4)N1'—Ag—N2'—C10'177 (5)
P2—C41—C42—C43−176.0 (2)P1—Ag—N2'—C10'−82 (4)
C41—C42—C43—C44−0.7 (5)N2—Ag—N2'—C10'−15 (11)
C42—C43—C44—C451.2 (5)N1—Ag—N2'—C11'−7(3)
C43—C44—C45—C46−0.4 (5)P2—Ag—N2'—C11'−119 (4)
C42—C41—C46—C451.3 (4)N1'—Ag—N2'—C11'−8(4)
P2—C41—C46—C45176.5 (2)P1—Ag—N2'—C11'93 (4)
C44—C45—C46—C41−0.8 (5)N2—Ag—N2'—C11'160 (17)
C41—P2—C51—C52114.9 (3)C5'—C6'—N3'—O2'−156 (3)
C61i—P2—C51—C52−136.2 (2)C7'—C6'—N3'—O2'23 (4)
Ag—P2—C51—C52−1.6 (3)C5'—C6'—N3'—O1'16 (5)
C41—P2—C51—C56−62.7 (3)C7'—C6'—N3'—O1'−166 (4)

Symmetry codes: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C35—H35A···F4ii0.932.543.409 (4)155
C46—H46A···F50.932.503.398 (4)163

Symmetry codes: (ii) −x−1/2, y−1/2, −z+5/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2121).

References

  • Bruker (1999). SHELXTL Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ho, D. M. & Bau, R. (1983). Inorg. Chem.22, 4073–4079.
  • Rigaku (2000). CrystalClear Version 1.3.6. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Smith, G. F. & Cagle, F. W. M. (1947). J. Org. Chem.12, 781–784. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography