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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o319.
Published online 2010 January 9. doi:  10.1107/S1600536810000267
PMCID: PMC2979852

Bis(triphenyl­phospho­ranyl­idene)ammonium iodide

Abstract

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 [triangle]); Guzei et al. (2001 [triangle]); Handy et al. (1970 [triangle]); Kirtley et al. (1980 [triangle]); Lewis & Dance (2000 [triangle]); Seel et al. (1984 [triangle], 1985 [triangle]); Tebbe & Krauss (1990 [triangle]); Weller et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o319-scheme1.jpg

Experimental

Crystal data

  • C36H30NP2 +·I
  • M r = 665.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o319-efi1.jpg
  • 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 [triangle]) T min = 0.815, T max = 0.943
  • 52122 measured reflections
  • 13900 independent reflections
  • 11771 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 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 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000267/ci2990Isup2.hkl

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

Acknowledgments

The authors thank the EPSRC for funding the crystallographic facilities.

supplementary crystallographic information

Comment

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).

Experimental

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

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

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
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.

Crystal data

C36H30NP2+·IF(000) = 2688
Mr = 665.45Dx = 1.451 Mg m3
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 mm1
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

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer13900 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode11771 reflections with I > 2σ(I)
10cm confocal mirrorsRint = 0.054
Detector resolution: 4096x4096pixels / 62x62mm pixels mm-1θmax = 27.5°, θmin = 2.9°
[var phi] 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

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 = 1.11w = 1/[σ2(Fo2) + 23.1366P] where P = (Fo2 + 2Fc2)/3
13900 reflections(Δ/σ)max = 0.002
721 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = −0.59 e Å3

Special details

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)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2990).

References

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