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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o319
https://doi.org/10.1107/S1600536810000267

Bis(tri­phenyl­phospho­ranyl­­idene)ammonium iodide

Michael A. Beckett,a Peter N. Horton,b* Michael B. Hursthouseb and James L. Timmisa

aSchool of Chemistry, University of Wales, Bangor LL57 2UW, Wales, and bSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England
*Correspondence e-mail: pnh@soton.ac.uk

(Received 14 December 2009; accepted 4 January 2010; online 9 January 2010)

The title compound, C36H30NP2+·I−, was obtained accidently from crystallization of a reaction mixture containing [(Ph3P)2N]OH and B(OH)3, which was contaminated with MeI. There are two independent [(Ph3P)2N]+ cations and two I− anions within the asymmetric unit. The central PNP angles are non-linear [137.6 (2) and 134.4 (2)°] and the phenyl substituents on P centres adopt different conformations within these two cations.

Related literature

For crystal structures containing the [(Ph3P)2N]+ cation, see: Glidewell & Holden (1982[Glidewell, C. & Holden, H. D. (1982). J. Organomet. Chem. 226, 171-181.]); Guzei et al. (2001[Guzei, I. A., Dougan, J. S. & Treichel, P. M. (2001). Acta Cryst. C57, 1060-1061.]); Handy et al. (1970[Handy, L. B., Ruff, J. K. & Dahl, L. F. (1970). J. Am. Chem. Soc. 92, 7327-7337.]); Kirtley et al. (1980[Kirtley, S. W., Chanton, J. P., Love, R. A., Tipton, D. L., Sorell, T. N. & Bau, R. (1980). J. Am. Chem. Soc. 102, 3451-3460.]); Lewis & Dance (2000[Lewis, G. R. & Dance, I. (2000). J. Chem. Soc. Dalton Trans. pp. 299-306.]); Seel et al. (1984[Seel, F., Kuhn, R. & Simon, G. (1984). Z. Naturforsch. Teil B, 39, 1622-1623.], 1985[Seel, F., Kuhn, R., Simon, G., Wagner, M., Krebs, B. & Dartmann, M. (1985). Z. Naturforsch. Teil B, 40, 1607-1617.]); Tebbe & Krauss (1990[Tebbe, K.-F. & Krauss, N. (1990). Acta Cryst. C46, 878-880.]); Weller et al. (1993[Weller, F., Nusshar, D. & Dehnicke, K. (1993). Z. Kristallogr. 208, 322-325.]).

[Scheme 1]

Experimental

Crystal data

  • C36H30NP2+·I−

  • Mr = 665.45

  • Monoclinic, P 21 /c

  • a = 29.6827 (6) Å

  • b = 10.1604 (2) Å

  • c = 20.2114 (4) Å

  • β = 91.337 (1)°

  • V = 6093.9 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.18 mm−1

  • T = 120 K

  • 0.18 × 0.10 × 0.05 mm
Data collection

  • Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.815, Tmax = 0.943

  • 52122 measured reflections

  • 13900 independent reflections

  • 11771 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.105

  • S = 1.11

  • 13900 reflections

  • 721 parameters

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.59 e Å−3

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810000267/ci2990sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000267/ci2990Isup2.hkl

checkCIF report


Comment top

There are numerous reports of single-crystal structures containing the [(Ph3P)2N]+ cation (Lewis & Dance, 2000) and usually this cation is partnered by an equally bulky anion, e.g. [(Ph3P)2N][Cr2(CO)10I] (Handy et al., 1970). Crystallographic studies on compounds containing [(Ph3P)2N]+ partnered with small anions are much more restricted e.g. [(Ph3P)2N][I3] (Tebbe & Krauss, 1990), [(Ph3P)2N][SCN] (Glidewell & Holden, 1982), [(Ph3P)2N][SNO2] (Seel et al., 1984), [(Ph3P)2N][SNO].CH3COCH3 (Seel et al., 1985), [(Ph3P)2N]Cl.PhCH3 (Weller et al., 1993), and [(Ph3P)2N][HSO4].CHCl3 (Guzei et al., 2001).

The unit cell of the title compound contains two independent [(Ph3P)2N]+ cations partnered by I- anions, with no significantly close anion/cation contacts. The conformations of the phenyl groups and the PNP angles differ in the two cations present, and in both cases the PNP angles are at the low end of the generally observed range, 130–180° (Lewis & Dance, 2000). Independent cations with disparate angles 139.1° and 180° have been observed in [(Ph3P)2N]3{Na[Mo3(CO)6(NO)3(OCH3)3(O)]} (Kirtley et al., 1980). The conformations of phenyl rings within the two cations are different with the cation containing N41 arranged so that there is an eclipsed interaction between phenyl rings of its two PPh3 moieties. This eclipsed arrangement is not apparent in the cation containing N1. Detailed analysis of inter- and intramolecular phenyl embraces within such cations has been described (Lewis & Dance, 2000).

Related literature top

For crystal structures containing the [(Ph3P)2N]+ cation, see: Glidewell & Holden (1982); Guzei et al. (2001); Handy et al. (1970); Kirtley et al. (1980); Lewis & Dance (2000); Seel et al. (1984, 1985); Tebbe & Krauss (1990); Weller et al. (1993).

Experimental top

A few crystals of [(Ph3P)2N] I, suitable for X-ray diffraction, were obtained from the crystallization of a reaction mixture containing [(Ph3P)2N][OH] (3.49 mmol) and B(OH)3 (1.08g, 17.43 mmol) in H2O/MeOH (15/15 cm3) which had been contaminated by MeI/ I-. MeI had been regularly used in the vicinity for methylation of amines.

Refinement top

H atoms were positioned geometrically [C-H = 0.95 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

There are numerous reports of single-crystal structures containing the [(Ph3P)2N]+ cation (Lewis & Dance, 2000) and usually this cation is partnered by an equally bulky anion, e.g. [(Ph3P)2N][Cr2(CO)10I] (Handy et al., 1970). Crystallographic studies on compounds containing [(Ph3P)2N]+ partnered with small anions are much more restricted e.g. [(Ph3P)2N][I3] (Tebbe & Krauss, 1990), [(Ph3P)2N][SCN] (Glidewell & Holden, 1982), [(Ph3P)2N][SNO2] (Seel et al., 1984), [(Ph3P)2N][SNO].CH3COCH3 (Seel et al., 1985), [(Ph3P)2N]Cl.PhCH3 (Weller et al., 1993), and [(Ph3P)2N][HSO4].CHCl3 (Guzei et al., 2001).

The unit cell of the title compound contains two independent [(Ph3P)2N]+ cations partnered by I- anions, with no significantly close anion/cation contacts. The conformations of the phenyl groups and the PNP angles differ in the two cations present, and in both cases the PNP angles are at the low end of the generally observed range, 130–180° (Lewis & Dance, 2000). Independent cations with disparate angles 139.1° and 180° have been observed in [(Ph3P)2N]3{Na[Mo3(CO)6(NO)3(OCH3)3(O)]} (Kirtley et al., 1980). The conformations of phenyl rings within the two cations are different with the cation containing N41 arranged so that there is an eclipsed interaction between phenyl rings of its two PPh3 moieties. This eclipsed arrangement is not apparent in the cation containing N1. Detailed analysis of inter- and intramolecular phenyl embraces within such cations has been described (Lewis & Dance, 2000).

For crystal structures containing the [(Ph3P)2N]+ cation, see: Glidewell & Holden (1982); Guzei et al. (2001); Handy et al. (1970); Kirtley et al. (1980); Lewis & Dance (2000); Seel et al. (1984, 1985); Tebbe & Krauss (1990); Weller et al. (1993).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of one of the two independent ionic units of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Bis(triphenylphosphoranylidene)ammonium iodide top
Crystal data top
C36H30NP2+·I−F(000) = 2688
Mr = 665.45Dx = 1.451 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14269 reflections
a = 29.6827 (6) Åθ = 2.9–27.5°
b = 10.1604 (2) ŵ = 1.18 mm−1
c = 20.2114 (4) ÅT = 120 K
β = 91.337 (1)°Slab, colourless
V = 6093.9 (2) Å30.18 × 0.10 × 0.05 mm
Z = 8
Data collection top
Bruker–Nonius APEXII CCD camera on κ-goniostat
diffractometer		13900 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode11771 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.054
Detector resolution: 4096x4096pixels / 62x62mm pixels mm-1θmax = 27.5°, θmin = 2.9°
φ and ω scansh = −38→38
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		k = −13→13
Tmin = 0.815, Tmax = 0.943l = −26→26
52122 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + 23.1366P]
where P = (Fo2 + 2Fc2)/3
13900 reflections(Δ/σ)max = 0.002
721 parametersΔρmax = 0.64 e Å−3
0 restraintsΔρmin = −0.59 e Å−3
Crystal data top
C36H30NP2+·I−V = 6093.9 (2) Å3
Mr = 665.45Z = 8
Monoclinic, P21/cMo Kα radiation
a = 29.6827 (6) ŵ = 1.18 mm−1
b = 10.1604 (2) ÅT = 120 K
c = 20.2114 (4) Å0.18 × 0.10 × 0.05 mm
β = 91.337 (1)°
Data collection top
Bruker–Nonius APEXII CCD camera on κ-goniostat
diffractometer		13900 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)		11771 reflections with I > 2σ(I)
Tmin = 0.815, Tmax = 0.943Rint = 0.054
52122 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + 23.1366P]
where P = (Fo2 + 2Fc2)/3
13900 reflectionsΔρmax = 0.64 e Å−3
721 parametersΔρmin = −0.59 e Å−3
Special details top

Experimental. SADABS was used to perform the Absorption correction Parameter refinement on 49041 reflections reduced R(int) from 0.1282 to 0.0578 Ratio of minimum to maximum apparent transmission: 0.905943 The given Tmin and Tmax were generated using the SHELX SIZE command

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*/Ueq
I10.369635 (8)−0.03183 (2)0.279022 (13)0.02336 (7)
I20.132635 (8)0.79725 (2)0.522407 (13)0.02426 (7)
C10.44904 (12)0.1172 (4)−0.13846 (17)0.0166 (7)
C20.48299 (12)0.0265 (4)−0.15317 (19)0.0220 (8)
H20.4791−0.0644−0.14380.026*
C30.52246 (13)0.0712 (5)−0.1817 (2)0.0296 (9)
H30.54580.0108−0.19140.036*
C40.52758 (14)0.2024 (5)−0.1958 (2)0.0313 (10)
H40.55430.2320−0.21610.038*
C50.49427 (14)0.2922 (4)−0.1807 (2)0.0287 (9)
H50.49850.3830−0.18980.034*
C60.45437 (12)0.2496 (4)−0.15225 (18)0.0205 (8)
H60.43120.3107−0.14250.025*
C70.40561 (12)−0.0902 (3)−0.06631 (18)0.0168 (7)
C80.43838 (12)−0.0866 (4)−0.01529 (19)0.0211 (8)
H80.4550−0.0082−0.00710.025*
C90.44652 (14)−0.1973 (4)0.0233 (2)0.0279 (9)
H90.4687−0.19460.05790.033*
C100.42216 (15)−0.3126 (4)0.0115 (2)0.0320 (10)
H100.4276−0.38800.03830.038*
C110.39005 (16)−0.3173 (4)−0.0393 (2)0.0367 (11)
H110.3736−0.3961−0.04740.044*
C120.38185 (14)−0.2067 (4)−0.0786 (2)0.0275 (9)
H120.3601−0.2106−0.11380.033*
C130.36500 (12)0.0223 (4)−0.18820 (18)0.0176 (7)
C140.38140 (15)−0.0762 (4)−0.2293 (2)0.0321 (10)
H140.4059−0.1298−0.21470.039*
C150.36180 (17)−0.0955 (4)−0.2915 (2)0.0379 (11)
H150.3733−0.1615−0.31980.045*
C160.32557 (14)−0.0191 (4)−0.3126 (2)0.0278 (9)
H160.3121−0.0332−0.35510.033*
C170.30910 (13)0.0775 (4)−0.27161 (19)0.0231 (8)
H170.28420.1299−0.28590.028*
C180.32898 (12)0.0983 (4)−0.20930 (18)0.0198 (8)
H180.31770.1651−0.18130.024*
C210.31812 (12)0.0474 (4)0.02718 (18)0.0189 (7)
C220.27423 (14)0.0241 (4)0.00151 (19)0.0272 (9)
H220.26020.0869−0.02700.033*
C230.25146 (15)−0.0907 (4)0.0180 (2)0.0299 (9)
H230.2219−0.10610.00070.036*
C240.27177 (15)−0.1817 (4)0.0593 (2)0.0271 (9)
H240.2565−0.26090.06960.033*
C250.31401 (15)−0.1585 (4)0.0855 (2)0.0358 (11)
H250.3273−0.22060.11520.043*
C260.33761 (14)−0.0455 (4)0.0693 (2)0.0313 (10)
H260.3671−0.03170.08700.038*
C270.39002 (12)0.2361 (4)0.05878 (17)0.0180 (7)
C280.43080 (14)0.2866 (4)0.0371 (2)0.0253 (8)
H280.43650.2919−0.00890.030*
C290.46323 (15)0.3293 (4)0.0834 (2)0.0308 (9)
H290.49100.36430.06880.037*
C300.45520 (15)0.3209 (4)0.1501 (2)0.0301 (9)
H300.47750.34980.18140.036*
C310.41511 (15)0.2708 (4)0.1716 (2)0.0305 (9)
H310.40990.26540.21770.037*
C320.38215 (14)0.2280 (4)0.12689 (19)0.0278 (9)
H320.35450.19360.14220.033*
C330.30720 (12)0.3182 (3)−0.01112 (17)0.0162 (7)
C340.30652 (13)0.3962 (4)−0.0675 (2)0.0220 (8)
H340.32770.3817−0.10120.026*
C350.27452 (14)0.4961 (4)−0.0745 (2)0.0264 (9)
H350.27420.5499−0.11290.032*
C360.24337 (14)0.5172 (4)−0.0259 (2)0.0289 (9)
H360.22120.5839−0.03160.035*
C370.24440 (13)0.4413 (4)0.0312 (2)0.0284 (9)
H370.22340.45760.06490.034*
C380.27615 (12)0.3414 (4)0.03915 (19)0.0212 (8)
H380.27680.28920.07820.025*
N10.36970 (10)0.1700 (3)−0.07309 (14)0.0184 (6)
P10.39496 (3)0.05850 (9)−0.11203 (4)0.01427 (18)
P20.34805 (3)0.18839 (9)−0.00264 (4)0.01560 (18)
C410.18730 (11)0.2625 (3)0.25464 (17)0.0145 (7)
C420.17620 (13)0.2292 (4)0.18920 (19)0.0203 (8)
H420.15050.26720.16780.024*
C430.20287 (14)0.1400 (4)0.1553 (2)0.0267 (9)
H430.19550.11830.11070.032*
C440.24003 (13)0.0829 (4)0.1866 (2)0.0240 (8)
H440.25800.02210.16320.029*
C450.25116 (12)0.1138 (4)0.2517 (2)0.0220 (8)
H450.27650.07380.27310.026*
C460.22500 (12)0.2037 (4)0.28578 (18)0.0186 (7)
H460.23270.22540.33030.022*
C470.15111 (11)0.3477 (4)0.38024 (17)0.0160 (7)
C480.14568 (13)0.2155 (4)0.39693 (19)0.0213 (8)
H480.14940.14950.36420.026*
C490.13478 (13)0.1795 (4)0.46110 (19)0.0243 (8)
H490.13140.08930.47240.029*
C500.12895 (13)0.2764 (4)0.50829 (19)0.0249 (8)
H500.12160.25210.55210.030*
C510.13368 (13)0.4089 (4)0.49246 (19)0.0220 (8)
H510.12910.47440.52510.026*
C520.14509 (12)0.4449 (4)0.42891 (18)0.0183 (7)
H520.14890.53520.41810.022*
C530.19486 (11)0.5331 (3)0.28942 (18)0.0175 (7)
C540.22588 (12)0.5664 (4)0.3396 (2)0.0218 (8)
H540.22670.51760.37970.026*
C550.25540 (13)0.6702 (4)0.3312 (2)0.0270 (9)
H550.27610.69340.36580.032*
C560.25474 (14)0.7405 (4)0.2723 (2)0.0301 (10)
H560.27530.81100.26640.036*
C570.22425 (14)0.7084 (4)0.2223 (2)0.0267 (9)
H570.22350.75810.18250.032*
C580.19470 (12)0.6039 (4)0.22984 (19)0.0189 (7)
H580.17440.58050.19470.023*
C610.03503 (12)0.4829 (4)0.33008 (18)0.0180 (7)
C620.03190 (12)0.3542 (4)0.35411 (19)0.0204 (8)
H620.05010.28650.33640.024*
C630.00190 (13)0.3261 (4)0.40412 (19)0.0251 (8)
H63−0.00060.23860.42020.030*
C64−0.02413 (14)0.4245 (5)0.4305 (2)0.0291 (9)
H64−0.04450.40450.46460.035*
C65−0.02069 (14)0.5522 (4)0.4075 (2)0.0269 (9)
H65−0.03870.61940.42600.032*
C660.00901 (13)0.5831 (4)0.3575 (2)0.0242 (8)
H660.01160.67110.34210.029*
C670.03590 (12)0.4853 (3)0.18693 (17)0.0160 (7)
C680.05620 (13)0.4409 (4)0.13041 (19)0.0224 (8)
H680.08800.42970.12990.027*
C690.02988 (14)0.4124 (4)0.0739 (2)0.0265 (9)
H690.04380.38110.03510.032*
C70−0.01626 (14)0.4298 (4)0.0745 (2)0.0262 (9)
H70−0.03430.40840.03650.031*
C71−0.03612 (13)0.4789 (4)0.1309 (2)0.0286 (9)
H71−0.06770.49370.13090.034*
C72−0.01038 (12)0.5063 (4)0.18714 (19)0.0217 (8)
H72−0.02420.53930.22570.026*
C730.08879 (12)0.6811 (3)0.26314 (18)0.0157 (7)
C740.09200 (12)0.7526 (4)0.20413 (19)0.0211 (8)
H740.07860.72010.16430.025*
C750.11520 (13)0.8723 (4)0.2046 (2)0.0243 (8)
H750.11670.92280.16510.029*
C760.13587 (13)0.9175 (4)0.2620 (2)0.0244 (8)
H760.15250.99730.26140.029*
C770.13264 (12)0.8477 (4)0.3206 (2)0.0210 (8)
H770.14700.87970.35980.025*
C780.10834 (12)0.7309 (4)0.32183 (19)0.0198 (8)
H780.10500.68490.36230.024*
N410.11134 (10)0.4116 (3)0.25563 (14)0.0159 (6)
P410.15782 (3)0.39312 (9)0.29476 (4)0.01339 (17)
P420.07035 (3)0.51324 (9)0.26050 (4)0.01424 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01942 (12)0.02321 (13)0.02771 (14)−0.00042 (10)0.00625 (9)−0.00172 (10)
I20.02414 (13)0.02105 (13)0.02784 (14)−0.00082 (10)0.00618 (10)0.00332 (10)
C10.0161 (17)0.0210 (18)0.0129 (16)−0.0035 (14)0.0019 (13)−0.0014 (14)
C20.0157 (17)0.031 (2)0.0190 (19)−0.0015 (15)−0.0007 (14)−0.0042 (16)
C30.0193 (19)0.046 (3)0.024 (2)0.0003 (18)0.0038 (16)−0.0007 (19)
C40.023 (2)0.051 (3)0.020 (2)−0.0071 (19)0.0028 (16)0.0096 (19)
C50.034 (2)0.033 (2)0.019 (2)−0.0098 (18)−0.0063 (16)0.0097 (17)
C60.0183 (18)0.0261 (19)0.0171 (18)−0.0017 (15)−0.0030 (14)0.0017 (15)
C70.0163 (17)0.0158 (17)0.0184 (18)0.0025 (13)0.0006 (13)−0.0007 (14)
C80.0188 (18)0.0200 (18)0.024 (2)0.0012 (15)−0.0031 (15)0.0003 (15)
C90.029 (2)0.031 (2)0.024 (2)0.0043 (17)−0.0087 (16)0.0006 (17)
C100.037 (2)0.024 (2)0.035 (2)0.0031 (18)−0.0048 (19)0.0105 (18)
C110.039 (3)0.024 (2)0.047 (3)−0.0070 (19)−0.014 (2)0.005 (2)
C120.027 (2)0.025 (2)0.030 (2)−0.0044 (17)−0.0104 (17)0.0044 (17)
C130.0188 (17)0.0188 (17)0.0151 (17)0.0002 (14)−0.0021 (13)−0.0032 (14)
C140.037 (2)0.027 (2)0.031 (2)0.0196 (18)−0.0196 (19)−0.0144 (18)
C150.051 (3)0.032 (2)0.030 (2)0.017 (2)−0.016 (2)−0.0155 (19)
C160.035 (2)0.026 (2)0.023 (2)0.0003 (17)−0.0132 (17)−0.0004 (17)
C170.0218 (19)0.0241 (19)0.023 (2)0.0003 (15)−0.0064 (15)0.0060 (16)
C180.0191 (18)0.0210 (18)0.0194 (18)0.0041 (14)0.0021 (14)0.0009 (15)
C210.0239 (19)0.0162 (17)0.0167 (18)0.0004 (14)0.0044 (14)0.0009 (14)
C220.038 (2)0.026 (2)0.0174 (19)−0.0094 (18)−0.0078 (16)0.0025 (16)
C230.038 (2)0.026 (2)0.025 (2)−0.0111 (18)−0.0047 (18)−0.0004 (17)
C240.040 (2)0.0174 (19)0.024 (2)−0.0059 (17)0.0103 (17)−0.0001 (16)
C250.036 (2)0.026 (2)0.046 (3)0.0044 (19)0.009 (2)0.018 (2)
C260.026 (2)0.029 (2)0.039 (3)0.0008 (17)0.0036 (18)0.0106 (19)
C270.0237 (19)0.0171 (17)0.0133 (17)0.0034 (14)0.0008 (14)0.0003 (14)
C280.029 (2)0.026 (2)0.0206 (19)−0.0052 (17)0.0025 (16)−0.0015 (16)
C290.030 (2)0.030 (2)0.032 (2)−0.0066 (18)−0.0048 (18)−0.0044 (18)
C300.033 (2)0.030 (2)0.027 (2)0.0011 (18)−0.0104 (17)−0.0064 (18)
C310.037 (2)0.036 (2)0.019 (2)0.0053 (19)−0.0081 (17)0.0000 (18)
C320.028 (2)0.039 (2)0.0166 (19)0.0016 (18)0.0032 (16)0.0030 (17)
C330.0170 (17)0.0163 (17)0.0153 (17)−0.0022 (13)−0.0019 (13)−0.0026 (14)
C340.0228 (19)0.0147 (17)0.029 (2)0.0032 (14)0.0043 (15)−0.0015 (15)
C350.032 (2)0.0197 (19)0.027 (2)0.0052 (16)−0.0049 (17)0.0000 (16)
C360.024 (2)0.022 (2)0.040 (2)0.0064 (16)−0.0063 (18)−0.0071 (18)
C370.022 (2)0.033 (2)0.030 (2)0.0017 (17)0.0065 (16)−0.0112 (18)
C380.0203 (18)0.0225 (19)0.0207 (19)−0.0007 (15)0.0019 (15)−0.0001 (15)
N10.0237 (16)0.0204 (15)0.0113 (14)0.0031 (13)0.0037 (12)0.0009 (12)
P10.0149 (4)0.0145 (4)0.0134 (4)0.0005 (3)−0.0004 (3)−0.0008 (3)
P20.0184 (4)0.0151 (4)0.0134 (4)0.0010 (3)0.0019 (3)0.0003 (3)
C410.0110 (15)0.0156 (16)0.0171 (17)−0.0004 (13)0.0027 (13)0.0001 (13)
C420.0203 (18)0.0213 (18)0.0192 (18)0.0023 (15)−0.0004 (14)−0.0020 (15)
C430.033 (2)0.026 (2)0.021 (2)0.0062 (17)−0.0004 (16)−0.0081 (17)
C440.027 (2)0.0175 (18)0.028 (2)0.0026 (15)0.0098 (16)−0.0031 (16)
C450.0153 (17)0.0200 (18)0.031 (2)0.0028 (14)0.0016 (15)0.0006 (16)
C460.0191 (18)0.0187 (17)0.0181 (18)−0.0027 (14)0.0011 (14)−0.0010 (14)
C470.0132 (16)0.0198 (17)0.0151 (17)−0.0007 (13)0.0003 (13)0.0023 (14)
C480.0254 (19)0.0190 (18)0.0195 (19)0.0005 (15)−0.0009 (15)0.0014 (15)
C490.025 (2)0.024 (2)0.024 (2)−0.0038 (16)−0.0006 (16)0.0048 (16)
C500.027 (2)0.030 (2)0.0177 (19)−0.0053 (17)0.0030 (15)0.0048 (16)
C510.026 (2)0.0241 (19)0.0158 (18)−0.0023 (16)−0.0004 (15)−0.0031 (15)
C520.0201 (18)0.0177 (17)0.0169 (18)−0.0010 (14)−0.0015 (14)0.0001 (14)
C530.0143 (16)0.0148 (17)0.0236 (19)−0.0003 (13)0.0033 (14)−0.0026 (14)
C540.0217 (19)0.0186 (18)0.025 (2)0.0005 (15)−0.0033 (15)−0.0003 (15)
C550.022 (2)0.023 (2)0.036 (2)−0.0027 (16)−0.0007 (17)−0.0083 (18)
C560.024 (2)0.0173 (19)0.050 (3)−0.0054 (16)0.0124 (19)−0.0062 (18)
C570.032 (2)0.0196 (19)0.029 (2)−0.0010 (16)0.0130 (17)0.0052 (16)
C580.0201 (18)0.0167 (17)0.0203 (18)−0.0003 (14)0.0068 (14)0.0007 (14)
C610.0163 (17)0.0194 (18)0.0184 (18)−0.0022 (14)0.0017 (14)0.0022 (14)
C620.0172 (17)0.0198 (18)0.0242 (19)0.0011 (14)0.0014 (14)−0.0012 (15)
C630.028 (2)0.027 (2)0.0207 (19)−0.0085 (17)0.0011 (16)0.0049 (16)
C640.025 (2)0.043 (3)0.020 (2)−0.0050 (18)0.0033 (16)−0.0023 (18)
C650.026 (2)0.027 (2)0.028 (2)−0.0034 (17)0.0087 (16)−0.0079 (17)
C660.026 (2)0.0185 (18)0.028 (2)0.0015 (15)0.0056 (16)−0.0038 (16)
C670.0188 (17)0.0129 (16)0.0162 (17)−0.0010 (13)−0.0027 (13)0.0018 (13)
C680.0233 (19)0.026 (2)0.0180 (18)0.0040 (16)−0.0029 (15)−0.0019 (16)
C690.038 (2)0.023 (2)0.0183 (19)0.0039 (17)−0.0049 (17)0.0002 (16)
C700.030 (2)0.025 (2)0.023 (2)−0.0083 (17)−0.0126 (16)0.0086 (16)
C710.0167 (18)0.036 (2)0.033 (2)−0.0052 (17)−0.0039 (16)0.0116 (19)
C720.0192 (18)0.026 (2)0.0198 (19)0.0016 (15)0.0031 (14)0.0049 (16)
C730.0165 (17)0.0117 (16)0.0190 (17)0.0029 (13)0.0006 (13)−0.0013 (13)
C740.0216 (19)0.0197 (18)0.0218 (19)0.0005 (15)−0.0034 (15)−0.0013 (15)
C750.029 (2)0.0186 (18)0.025 (2)−0.0003 (16)0.0047 (16)0.0048 (16)
C760.028 (2)0.0161 (18)0.030 (2)−0.0016 (15)0.0056 (16)−0.0026 (16)
C770.0196 (18)0.0177 (18)0.026 (2)0.0013 (14)−0.0022 (15)−0.0046 (15)
C780.0193 (18)0.0192 (18)0.0209 (19)0.0049 (14)−0.0013 (14)0.0021 (15)
N410.0173 (15)0.0158 (14)0.0145 (14)0.0011 (12)−0.0007 (11)−0.0003 (12)
P410.0143 (4)0.0124 (4)0.0134 (4)−0.0002 (3)0.0000 (3)0.0003 (3)
P420.0140 (4)0.0143 (4)0.0144 (4)−0.0001 (3)0.0009 (3)0.0005 (3)
Geometric parameters (Å, º) top
C1—C61.383 (5)C41—C421.397 (5)
C1—C21.403 (5)C41—C461.405 (5)
C1—P11.805 (4)C41—P411.793 (4)
C2—C31.394 (5)C42—C431.393 (5)
C2—H20.95C42—H420.95
C3—C41.372 (6)C43—C441.385 (6)
C3—H30.95C43—H430.95
C4—C51.384 (6)C44—C451.387 (6)
C4—H40.95C44—H440.95
C5—C61.397 (5)C45—C461.391 (5)
C5—H50.95C45—H450.95
C6—H60.95C46—H460.95
C7—C121.398 (5)C47—C481.395 (5)
C7—C81.402 (5)C47—C521.408 (5)
C7—P11.795 (4)C47—P411.804 (4)
C8—C91.387 (5)C48—C491.393 (5)
C8—H80.95C48—H480.95
C9—C101.394 (6)C49—C501.385 (6)
C9—H90.95C49—H490.95
C10—C111.385 (6)C50—C511.391 (5)
C10—H100.95C50—H500.95
C11—C121.394 (6)C51—C521.385 (5)
C11—H110.95C51—H510.95
C12—H120.95C52—H520.95
C13—C181.379 (5)C53—C541.396 (5)
C13—C141.395 (5)C53—C581.403 (5)
C13—P11.798 (4)C53—P411.802 (4)
C14—C151.387 (6)C54—C551.384 (5)
C14—H140.95C54—H540.95
C15—C161.385 (6)C55—C561.388 (6)
C15—H150.95C55—H550.95
C16—C171.381 (6)C56—C571.380 (6)
C16—H160.95C56—H560.95
C17—C181.394 (5)C57—C581.387 (5)
C17—H170.95C57—H570.95
C18—H180.95C58—H580.95
C21—C261.388 (5)C61—C621.398 (5)
C21—C221.411 (5)C61—C661.400 (5)
C21—P21.797 (4)C61—P421.800 (4)
C22—C231.392 (6)C62—C631.392 (5)
C22—H220.95C62—H620.95
C23—C241.375 (6)C63—C641.378 (6)
C23—H230.95C63—H630.95
C24—C251.370 (6)C64—C651.383 (6)
C24—H240.95C64—H640.95
C25—C261.389 (6)C65—C661.393 (5)
C25—H250.95C65—H650.95
C26—H260.95C66—H660.95
C27—C281.395 (5)C67—C681.380 (5)
C27—C321.404 (5)C67—C721.390 (5)
C27—P21.804 (4)C67—P421.807 (4)
C28—C291.396 (6)C68—C691.398 (5)
C28—H280.95C68—H680.95
C29—C301.378 (6)C69—C701.381 (6)
C29—H290.95C69—H690.95
C30—C311.374 (6)C70—C711.388 (6)
C30—H300.95C70—H700.95
C31—C321.386 (6)C71—C721.383 (6)
C31—H310.95C71—H710.95
C32—H320.95C72—H720.95
C33—C341.388 (5)C73—C741.402 (5)
C33—C381.408 (5)C73—C781.403 (5)
C33—P21.797 (4)C73—P421.792 (4)
C34—C351.395 (5)C74—C751.397 (5)
C34—H340.95C74—H740.95
C35—C361.382 (6)C75—C761.378 (6)
C35—H350.95C75—H750.95
C36—C371.387 (6)C76—C771.385 (6)
C36—H360.95C76—H760.95
C37—C381.392 (5)C77—C781.389 (5)
C37—H370.95C77—H770.95
C38—H380.95C78—H780.95
N1—P11.579 (3)N41—P411.585 (3)
N1—P21.587 (3)N41—P421.601 (3)
C6—C1—C2120.7 (3)C42—C41—C46119.2 (3)
C6—C1—P1119.2 (3)C42—C41—P41120.1 (3)
C2—C1—P1119.6 (3)C46—C41—P41120.3 (3)
C3—C2—C1119.2 (4)C43—C42—C41119.9 (3)
C3—C2—H2120.4C43—C42—H42120.0
C1—C2—H2120.4C41—C42—H42120.0
C4—C3—C2120.1 (4)C44—C43—C42120.3 (4)
C4—C3—H3120.0C44—C43—H43119.9
C2—C3—H3120.0C42—C43—H43119.9
C3—C4—C5120.7 (4)C43—C44—C45120.5 (4)
C3—C4—H4119.6C43—C44—H44119.8
C5—C4—H4119.6C45—C44—H44119.8
C4—C5—C6120.2 (4)C44—C45—C46119.7 (3)
C4—C5—H5119.9C44—C45—H45120.2
C6—C5—H5119.9C46—C45—H45120.2
C1—C6—C5119.1 (4)C45—C46—C41120.4 (3)
C1—C6—H6120.5C45—C46—H46119.8
C5—C6—H6120.5C41—C46—H46119.8
C12—C7—C8119.4 (3)C48—C47—C52119.3 (3)
C12—C7—P1122.7 (3)C48—C47—P41119.6 (3)
C8—C7—P1117.9 (3)C52—C47—P41120.5 (3)
C9—C8—C7120.1 (4)C49—C48—C47120.6 (4)
C9—C8—H8119.9C49—C48—H48119.7
C7—C8—H8119.9C47—C48—H48119.7
C8—C9—C10120.1 (4)C50—C49—C48119.3 (4)
C8—C9—H9120.0C50—C49—H49120.3
C10—C9—H9120.0C48—C49—H49120.3
C11—C10—C9120.1 (4)C49—C50—C51121.0 (4)
C11—C10—H10119.9C49—C50—H50119.5
C9—C10—H10119.9C51—C50—H50119.5
C10—C11—C12120.2 (4)C52—C51—C50119.8 (4)
C10—C11—H11119.9C52—C51—H51120.1
C12—C11—H11119.9C50—C51—H51120.1
C11—C12—C7120.1 (4)C51—C52—C47120.0 (3)
C11—C12—H12120.0C51—C52—H52120.0
C7—C12—H12120.0C47—C52—H52120.0
C18—C13—C14119.8 (3)C54—C53—C58119.2 (3)
C18—C13—P1121.0 (3)C54—C53—P41122.7 (3)
C14—C13—P1119.0 (3)C58—C53—P41117.8 (3)
C15—C14—C13119.8 (4)C55—C54—C53120.3 (4)
C15—C14—H14120.1C55—C54—H54119.9
C13—C14—H14120.1C53—C54—H54119.9
C16—C15—C14120.3 (4)C54—C55—C56120.1 (4)
C16—C15—H15119.8C54—C55—H55120.0
C14—C15—H15119.8C56—C55—H55120.0
C17—C16—C15119.8 (4)C57—C56—C55120.2 (4)
C17—C16—H16120.1C57—C56—H56119.9
C15—C16—H16120.1C55—C56—H56119.9
C16—C17—C18120.0 (4)C56—C57—C58120.4 (4)
C16—C17—H17120.0C56—C57—H57119.8
C18—C17—H17120.0C58—C57—H57119.8
C13—C18—C17120.2 (4)C57—C58—C53119.8 (4)
C13—C18—H18119.9C57—C58—H58120.1
C17—C18—H18119.9C53—C58—H58120.1
C26—C21—C22118.7 (4)C62—C61—C66120.1 (3)
C26—C21—P2123.0 (3)C62—C61—P42118.4 (3)
C22—C21—P2118.0 (3)C66—C61—P42121.4 (3)
C23—C22—C21120.1 (4)C63—C62—C61119.5 (4)
C23—C22—H22120.0C63—C62—H62120.2
C21—C22—H22120.0C61—C62—H62120.2
C24—C23—C22120.0 (4)C64—C63—C62120.3 (4)
C24—C23—H23120.0C64—C63—H63119.8
C22—C23—H23120.0C62—C63—H63119.8
C25—C24—C23120.2 (4)C63—C64—C65120.3 (4)
C25—C24—H24119.9C63—C64—H64119.8
C23—C24—H24119.9C65—C64—H64119.8
C24—C25—C26120.8 (4)C64—C65—C66120.6 (4)
C24—C25—H25119.6C64—C65—H65119.7
C26—C25—H25119.6C66—C65—H65119.7
C21—C26—C25120.1 (4)C65—C66—C61119.2 (4)
C21—C26—H26119.9C65—C66—H66120.4
C25—C26—H26119.9C61—C66—H66120.4
C28—C27—C32119.7 (4)C68—C67—C72120.2 (3)
C28—C27—P2118.2 (3)C68—C67—P42118.9 (3)
C32—C27—P2122.1 (3)C72—C67—P42120.9 (3)
C27—C28—C29119.6 (4)C67—C68—C69119.8 (4)
C27—C28—H28120.2C67—C68—H68120.1
C29—C28—H28120.2C69—C68—H68120.1
C30—C29—C28120.3 (4)C70—C69—C68120.1 (4)
C30—C29—H29119.9C70—C69—H69119.9
C28—C29—H29119.9C68—C69—H69119.9
C31—C30—C29120.2 (4)C69—C70—C71119.5 (4)
C31—C30—H30119.9C69—C70—H70120.2
C29—C30—H30119.9C71—C70—H70120.2
C30—C31—C32121.0 (4)C72—C71—C70120.7 (4)
C30—C31—H31119.5C72—C71—H71119.7
C32—C31—H31119.5C70—C71—H71119.7
C31—C32—C27119.3 (4)C71—C72—C67119.6 (4)
C31—C32—H32120.4C71—C72—H72120.2
C27—C32—H32120.4C67—C72—H72120.2
C34—C33—C38120.0 (3)C74—C73—C78119.8 (3)
C34—C33—P2119.6 (3)C74—C73—P42119.7 (3)
C38—C33—P2120.4 (3)C78—C73—P42119.2 (3)
C33—C34—C35119.7 (4)C75—C74—C73119.3 (4)
C33—C34—H34120.1C75—C74—H74120.4
C35—C34—H34120.1C73—C74—H74120.4
C36—C35—C34120.4 (4)C76—C75—C74120.3 (4)
C36—C35—H35119.8C76—C75—H75119.8
C34—C35—H35119.8C74—C75—H75119.8
C35—C36—C37120.2 (4)C75—C76—C77120.7 (4)
C35—C36—H36119.9C75—C76—H76119.6
C37—C36—H36119.9C77—C76—H76119.6
C36—C37—C38120.2 (4)C76—C77—C78120.0 (4)
C36—C37—H37119.9C76—C77—H77120.0
C38—C37—H37119.9C78—C77—H77120.0
C37—C38—C33119.4 (4)C77—C78—C73119.8 (3)
C37—C38—H38120.3C77—C78—H78120.1
C33—C38—H38120.3C73—C78—H78120.1
P1—N1—P2137.6 (2)P41—N41—P42134.4 (2)
N1—P1—C7115.30 (16)N41—P41—C41106.87 (16)
N1—P1—C13110.04 (17)N41—P41—C53113.68 (16)
C7—P1—C13110.25 (17)C41—P41—C53104.59 (16)
N1—P1—C1110.25 (17)N41—P41—C47113.20 (16)
C7—P1—C1106.47 (17)C41—P41—C47108.04 (16)
C13—P1—C1103.87 (17)C53—P41—C47109.91 (17)
N1—P2—C33106.68 (16)N41—P42—C73112.57 (16)
N1—P2—C21114.89 (17)N41—P42—C61113.26 (16)
C33—P2—C21106.23 (17)C73—P42—C61108.84 (17)
N1—P2—C27111.18 (17)N41—P42—C67105.34 (16)
C33—P2—C27108.79 (16)C73—P42—C67109.91 (16)
C21—P2—C27108.80 (17)C61—P42—C67106.69 (17)

Experimental details

Crystal data
Chemical formulaC36H30NP2+·I−
Mr665.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)29.6827 (6), 10.1604 (2), 20.2114 (4)
β (°) 91.337 (1)
V (Å3)6093.9 (2)
Z8
Radiation typeMo Kα
µ (mm−1)1.18
Crystal size (mm)0.18 × 0.10 × 0.05
Data collection
DiffractometerBruker–Nonius APEXII CCD camera on κ-goniostat
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.815, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections		52122, 13900, 11771
Rint0.054
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.105, 1.11
No. of reflections13900
No. of parameters721
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + 23.1366P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.64, −0.59

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

The authors thank the EPSRC for funding the crystallographic facilities.

References

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o319
https://doi.org/10.1107/S1600536810000267
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