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

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

aDepartment of Chemistry, Guangdong Medical College, Zhanjiang 524023, People's Republic of China.
*Correspondence e-mail: yingq666@sohu.com

(Received 15 November 2007; accepted 14 December 2007; online 21 December 2007)

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[Ho, D. M. & Bau, R. (1983). Inorg. Chem. 22, 4073-4079.]); Smith & Cagle (1947[Smith, G. F. & Cagle, F. W. M. (1947). J. Org. Chem. 12, 781-784.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2

  • Mr = 1906.38

  • Monoclinic, P 21 /n

  • 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[Rigaku (2000). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.816, Tmax = 1.000 (expected range = 0.543–0.665)

  • 22441 measured reflections

  • 6301 independent reflections

  • 5851 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 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

Table 1
Selected geometric parameters (Å, °)

Ag—N1 2.392 (6)
Ag—P2 2.3982 (7)
Ag—P1 2.4491 (7)
Ag—N2 2.451 (5)
N1—Ag—P2 115.8 (3)
N1—Ag—P1 100.1 (3)
P2—Ag—P1 144.11 (3)
N1—Ag—N2 68.51 (15)
P2—Ag—N2 103.1 (2)
P1—Ag—N2 90.9 (2)

Data collection: CrystalClear (Rigaku, 2000[Rigaku (2000). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1999[Bruker (1999). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

[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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] 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, 2 - z.
[Figure 2] Fig. 2. Crystal packing of the title compound
Bis[µ-methylenebis(diphenylphosphine)]bis[(5-nitro-1,10- phenanthroline)silver(I)] bis(hexafluoridoantimonate) top
Crystal data top
[Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2F(000) = 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 = 3.0–25.0°
b = 23.3993 (10) ŵ = 1.46 mm1
c = 13.5580 (11) ÅT = 293 K
β = 117.936 (2)°Prism, yellow
V = 3588.5 (4) Å30.35 × 0.35 × 0.28 mm
Z = 2
Data collection top
Rigaku Mercury 70 CCD
diffractometer
6301 independent reflections
Radiation source: fine-focus sealed tube5851 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 14.6306 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)
k = 2726
Tmin = 0.816, Tmax = 1.000l = 1615
22441 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0186P)2 + 5.1P]
where P = (Fo2 + 2Fc2)/3
6301 reflections(Δ/σ)max = 0.002
623 parametersΔρmax = 0.66 e Å3
486 restraintsΔρmin = 0.70 e Å3
Crystal data top
[Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2V = 3588.5 (4) Å3
Mr = 1906.38Z = 2
Monoclinic, P21/nMo Kα radiation
a = 12.8034 (7) ŵ = 1.46 mm1
b = 23.3993 (10) ÅT = 293 K
c = 13.5580 (11) Å0.35 × 0.35 × 0.28 mm
β = 117.936 (2)°
Data collection top
Rigaku Mercury 70 CCD
diffractometer
6301 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)
5851 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 1.000Rint = 0.026
22441 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030486 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.11Δρmax = 0.66 e Å3
6301 reflectionsΔρmin = 0.70 e Å3
623 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Ag0.023652 (17)0.075515 (9)1.091671 (17)0.01867 (6)
P10.17901 (6)0.06326 (3)0.94206 (6)0.01775 (16)
P20.19380 (6)0.02588 (3)1.22857 (6)0.01697 (15)
C210.2634 (2)0.00996 (12)0.9721 (2)0.0216 (6)
C220.3864 (3)0.00586 (13)0.9110 (3)0.0247 (7)
H22A0.42860.03250.85550.030*
C230.4457 (3)0.03785 (14)0.9330 (3)0.0326 (8)
H23A0.52740.04090.89130.039*
C240.3838 (3)0.07685 (15)1.0167 (3)0.0401 (9)
H24A0.42410.10591.03150.048*
C250.2625 (3)0.07299 (15)1.0786 (3)0.0385 (8)
H25A0.22110.09921.13510.046*
C260.2027 (3)0.02995 (13)1.0562 (3)0.0280 (7)
H26A0.12090.02761.09770.034*
C310.2520 (2)0.13177 (12)0.9320 (2)0.0205 (6)
C320.2280 (2)0.17707 (13)0.8787 (2)0.0253 (7)
H32A0.18660.17030.83890.030*
C330.2651 (3)0.23201 (13)0.8845 (3)0.0313 (8)
H33A0.24830.26200.84910.038*
C340.3271 (3)0.24197 (14)0.9432 (3)0.0357 (8)
H34A0.35130.27890.94800.043*
C350.3532 (3)0.19762 (15)0.9945 (3)0.0351 (8)
H35A0.39600.20461.03290.042*
C360.3163 (2)0.14242 (14)0.9894 (3)0.0274 (7)
H36A0.33430.11261.02420.033*
C410.1816 (2)0.02647 (12)1.3574 (2)0.0200 (6)
C420.2094 (3)0.07752 (14)1.4183 (3)0.0275 (7)
H42A0.23760.10851.39480.033*
C430.1952 (3)0.08225 (15)1.5130 (3)0.0330 (8)
H43A0.21310.11651.55250.040*
C440.1546 (3)0.03626 (16)1.5490 (3)0.0353 (8)
H44A0.14660.03931.61350.042*
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)
H52A0.28520.12811.18080.034*
C530.4631 (3)0.13370 (15)1.2712 (3)0.0389 (9)
H53A0.47090.16881.24300.047*
C540.5617 (3)0.10585 (16)1.3500 (3)0.0371 (8)
H54A0.63600.12231.37510.044*
C550.5510 (3)0.05397 (16)1.3916 (3)0.0349 (8)
H55A0.61820.03521.44390.042*
C560.4403 (2)0.02935 (14)1.3558 (3)0.0262 (7)
H56A0.43320.00541.38560.031*
C610.2118 (2)0.04967 (12)0.7965 (2)0.0206 (6)
H61A0.15950.07260.77910.025*
H61B0.29240.06130.74690.025*
C10.0907 (6)0.1990 (2)1.0194 (7)0.0286 (12)0.842 (4)
H1A0.12060.17480.98430.034*0.842 (4)
C20.0947 (6)0.2583 (2)1.0054 (5)0.0438 (16)0.842 (4)
H2A0.12700.27290.96190.053*0.842 (4)
C30.0510 (5)0.2940 (2)1.0557 (5)0.0445 (16)0.842 (4)
H3A0.05410.33321.04710.053*0.842 (4)
C40.0010 (5)0.2723 (2)1.1206 (4)0.0338 (12)0.842 (4)
C50.0497 (5)0.3045 (2)1.1798 (5)0.0424 (17)0.842 (4)
C60.1018 (4)0.2802 (2)1.2341 (4)0.0427 (13)0.842 (4)
H6A0.13640.30331.26660.051*0.842 (4)
C70.1057 (5)0.2198 (2)1.2435 (4)0.0323 (12)0.842 (4)
C80.1592 (4)0.1931 (2)1.3008 (4)0.0411 (12)0.842 (4)
H8A0.19690.21461.33240.049*0.842 (4)
C90.1552 (5)0.1351 (2)1.3094 (4)0.0417 (12)0.842 (4)
H9A0.19030.11651.34680.050*0.842 (4)
C100.0977 (5)0.1041 (2)1.2612 (5)0.0326 (13)0.842 (4)
H10A0.09430.06461.26900.039*0.842 (4)
C110.0517 (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)
N20.0478 (8)0.12770 (18)1.2050 (7)0.0233 (10)0.842 (4)
N30.0420 (4)0.36777 (18)1.1863 (4)0.0676 (16)0.842 (4)
O10.0046 (4)0.39241 (17)1.1320 (6)0.121 (3)0.842 (4)
O20.0729 (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'A0.14200.16280.98420.027*0.158 (4)
C2'0.116 (3)0.2481 (13)0.987 (3)0.027 (4)0.158 (4)
H2'A0.14800.25850.94050.032*0.158 (4)
C3'0.075 (3)0.2885 (12)1.031 (3)0.028 (4)0.158 (4)
H3'A0.08160.32691.01730.034*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'A0.02340.35111.13720.031*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'A0.15870.23901.33180.037*0.158 (4)
C9'0.127 (3)0.1569 (10)1.320 (2)0.031 (3)0.158 (4)
H9'A0.15760.14331.36560.038*0.158 (4)
C10'0.079 (3)0.1187 (11)1.271 (3)0.031 (3)0.158 (4)
H10B0.07560.07981.28620.037*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)
F10.0552 (2)0.15895 (13)1.3963 (3)0.0868 (9)
F20.09810 (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) top
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, º) top
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—C2139.37 (11)Ag—P2—C51—C56179.1 (2)
N1'—Ag—P1—C21149.1 (6)C56—C51—C52—C530.9 (5)
N2'—Ag—P1—C2180.6 (6)P2—C51—C52—C53178.5 (3)
N2—Ag—P1—C2174.73 (15)C51—C52—C53—C540.3 (5)
N1—Ag—P1—C3126.83 (17)C52—C53—C54—C550.3 (5)
P2—Ag—P1—C31155.60 (10)C53—C54—C55—C561.0 (5)
N1'—Ag—P1—C3132.9 (6)C54—C55—C56—C511.6 (5)
N2'—Ag—P1—C3135.7 (6)C52—C51—C56—C551.6 (4)
N2—Ag—P1—C3141.50 (15)P2—C51—C56—C55179.2 (2)
N1—Ag—P1—C6189.21 (17)C21—P1—C61—P2i49.57 (18)
P2—Ag—P1—C6188.35 (12)C31—P1—C61—P2i160.67 (15)
N1'—Ag—P1—C6183.2 (6)Ag—P1—C61—P2i81.92 (16)
N2'—Ag—P1—C61151.7 (6)C2—C1—N1—Ag174.5 (6)
N2—Ag—P1—C61157.54 (15)C4—C12—N1—Ag174.2 (5)
N1—Ag—P2—C5124.36 (19)C11—C12—N1—Ag3.4 (11)
N1'—Ag—P2—C5117.9 (7)P2—Ag—N1—C185.9 (8)
N2'—Ag—P2—C5190.1 (8)N1'—Ag—N1—C114 (18)
P1—Ag—P2—C51152.97 (11)N2'—Ag—N1—C1178.9 (18)
N2—Ag—P2—C5196.58 (17)P1—Ag—N1—C192.5 (8)
N1—Ag—P2—C4189.44 (18)N2—Ag—N1—C1179.5 (9)
N1'—Ag—P2—C4195.8 (7)P2—Ag—N1—C12100.1 (7)
N2'—Ag—P2—C4123.7 (8)N1'—Ag—N1—C12172 (19)
P1—Ag—P2—C4193.23 (11)N2'—Ag—N1—C127.1 (17)
N2—Ag—P2—C4117.21 (16)P1—Ag—N1—C1281.5 (8)
N1—Ag—P2—C61i152.98 (18)N2—Ag—N1—C125.5 (7)
N1'—Ag—P2—C61i146.6 (7)C9—C10—N2—C110.7 (11)
N2'—Ag—P2—C61i141.2 (8)C9—C10—N2—Ag168.8 (5)
P1—Ag—P2—C61i24.35 (12)C7—C11—N2—C100.9 (11)
N2—Ag—P2—C61i134.79 (17)C12—C11—N2—C10178.9 (7)
C31—P1—C21—C26133.8 (2)C7—C11—N2—Ag171.3 (5)
C61—P1—C21—C26117.8 (2)C12—C11—N2—Ag8.5 (9)
Ag—P1—C21—C2618.2 (3)N1—Ag—N2—C10176.9 (8)
C31—P1—C21—C2249.0 (3)P2—Ag—N2—C1070.2 (7)
C61—P1—C21—C2259.4 (3)N1'—Ag—N2—C10178.3 (19)
Ag—P1—C21—C22164.7 (2)N2'—Ag—N2—C10170 (15)
C26—C21—C22—C231.1 (4)P1—Ag—N2—C1076.4 (7)
P1—C21—C22—C23176.0 (2)N1—Ag—N2—C117.2 (6)
C21—C22—C23—C241.2 (5)P2—Ag—N2—C11120.1 (6)
C22—C23—C24—C250.5 (5)N1'—Ag—N2—C118.7 (18)
C23—C24—C25—C260.3 (6)N2'—Ag—N2—C1120 (14)
C24—C25—C26—C210.4 (5)P1—Ag—N2—C1193.2 (6)
C22—C21—C26—C250.3 (5)C6—C5—N3—O26.1 (8)
P1—C21—C26—C25176.9 (3)C4—C5—N3—O2171.9 (7)
C21—P1—C31—C3627.8 (3)C6—C5—N3—O1174.2 (5)
C61—P1—C31—C36138.0 (2)C4—C5—N3—O17.8 (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—C3276.9 (2)P1—Ag—N1'—C1'94 (5)
C36—C31—C32—C331.3 (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—C360.9 (5)P1—Ag—N1'—C12'79 (5)
C34—C35—C36—C310.1 (4)N2—Ag—N1'—C12'9 (4)
C32—C31—C36—C351.2 (4)C9'—C10'—N2'—C11'4 (7)
P1—C31—C36—C35169.2 (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—C4698.7 (2)C7'—C11'—N2'—Ag169 (3)
C51—P2—C41—C4248.9 (2)C12'—C11'—N2'—Ag6 (6)
C61i—P2—C41—C42157.5 (2)N1—Ag—N2'—C10'178 (5)
Ag—P2—C41—C4276.5 (2)P2—Ag—N2'—C10'66 (4)
C46—C41—C42—C430.5 (4)N1'—Ag—N2'—C10'177 (5)
P2—C41—C42—C43176.0 (2)P1—Ag—N2'—C10'82 (4)
C41—C42—C43—C440.7 (5)N2—Ag—N2'—C10'15 (11)
C42—C43—C44—C451.2 (5)N1—Ag—N2'—C11'7 (3)
C43—C44—C45—C460.4 (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—C410.8 (5)N2—Ag—N2'—C11'160 (17)
C41—P2—C51—C52114.9 (3)C5'—C6'—N3'—O2'156 (3)
C61i—P2—C51—C52136.2 (2)C7'—C6'—N3'—O2'23 (4)
Ag—P2—C51—C521.6 (3)C5'—C6'—N3'—O1'16 (5)
C41—P2—C51—C5662.7 (3)C7'—C6'—N3'—O1'166 (4)
Symmetry code: (i) x, y, z+2.
Hydrogen-bond geometry (Å, º) top
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 code: (ii) x1/2, y1/2, z+5/2.

Experimental details

Crystal data
Chemical formula[Ag2(C12H7N3O2)2(C25H22P2)2](SbF6)2
Mr1906.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)12.8034 (7), 23.3993 (10), 13.5580 (11)
β (°) 117.936 (2)
V3)3588.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.46
Crystal size (mm)0.35 × 0.35 × 0.28
Data collection
DiffractometerRigaku Mercury 70 CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2000)
Tmin, Tmax0.816, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
22441, 6301, 5851
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.060, 1.11
No. of reflections6301
No. of parameters623
No. of restraints486
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.70

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Selected geometric parameters (Å, º) top
Ag—N12.392 (6)Ag—P12.4491 (7)
Ag—P22.3982 (7)Ag—N22.451 (5)
N1—Ag—P2115.8 (3)N1—Ag—N268.51 (15)
N1—Ag—P1100.1 (3)P2—Ag—N2103.1 (2)
P2—Ag—P1144.11 (3)P1—Ag—N290.9 (2)
 

References

First citationBruker (1999). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHo, D. M. & Bau, R. (1983). Inorg. Chem. 22, 4073–4079.  CSD CrossRef CAS Web of Science Google Scholar
First citationRigaku (2000). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSmith, G. F. & Cagle, F. W. M. (1947). J. Org. Chem. 12, 781–784.  CrossRef PubMed CAS Web of Science Google Scholar

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