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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3186.
Published online 2010 November 17. doi:  10.1107/S1600536810046337
PMCID: PMC3011659

Bis(triphenylphosphine)iminium bromide acetonitrile monosolvate

Abstract

The title compound, C36H30NP2 +·Br·C2H3N, crystallized from a CH3CN/OEt2 solution as an acetonitrile solvate. The central P—N—P angle [142.88 (10)°] is significantly larger than in the corresponding chloride and iodide structures.

Related literature

Several bis­(triphenyl­phosphine)iminium halide structures have been determined. For [(Ph3P)2N]Cl, see: Knapp et al. (2010 [triangle]); for [(Ph3P)2N]Cl·B(OH)3, see: Andrews et al. (1983 [triangle]); for [(Ph3P)2N]Cl·CH3C6H5, see: Weller et al. (1993 [triangle]); for [(Ph3P)2N]Cl·CH2Cl2, see: Carroll et al. (1996 [triangle]); for [(Ph3P)2N]Cl·CH2Cl2·H2O, see: de Arellano (1997 [triangle]); for [(Ph3P)2N]I, see: Beckett et al. (2010 [triangle]). For a discussion of the [(Ph3P)2N]+ cation, see: Lewis et al. (2000 [triangle]). For the synthesis, see: Martinsen & Songstad (1977 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3186-scheme1.jpg

Experimental

Crystal data

  • C36H30NP2 +·Br·C2H3N
  • M r = 659.51
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3186-efi1.jpg
  • a = 19.7113 (6) Å
  • b = 15.9564 (5) Å
  • c = 20.3318 (6) Å
  • V = 6394.8 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.42 mm−1
  • T = 100 K
  • 0.20 × 0.20 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.765, T max = 0.805
  • 57718 measured reflections
  • 7749 independent reflections
  • 6140 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.085
  • S = 1.02
  • 7749 reflections
  • 391 parameters
  • Only H-atom displacement parameters refined
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg et al., 2010 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046337/fi2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046337/fi2100Isup2.hkl

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

Acknowledgments

Financial support by the Deutsche Forschungsgemeinschaft (DFG) and the Universität Freiburg is gratefully acknowledged.

supplementary crystallographic information

Comment

Crystal structures of [(Ph3P)2N]+ salts containing small counter anions are rare. Usually this cation is partnered by a bulky anion, while crystal structures containing small anions and especially halides remained unknown until recently. Only very recently the crystal structures of the halides [(Ph3P)2N]Cl (Knapp et al., 2010) and [(Ph3P)2N]I (Beckett et al., 2010) were determined. In contrast, crystal structures of [(Ph3P)2N]Cl containing solvate molecules are known for some time, e.g. [(Ph3P)2N]Cl.B(OH)3 (Andrews et al. (1983)), [(Ph3P)2N]Cl.CH3C6H5, (Weller et al. (1993)), [(Ph3P)2N]Cl.CH2Cl2 (Carroll et al. (1996)), [(Ph3P)2N]Cl.CH2Cl2.H2O (de Arellano (1997)).

[(Ph3P)2N]Br has been synthesized according to a published procedure (Martinsen et al., 1977) and single crystals suitable for X-ray diffraction were obtained by layering a CH3CN solution with diethyl ether. In contrast to the the crystal structures of [(Ph3P)2N]Cl (Knapp et al., 2010) and [(Ph3P)2N]I (Beckett et al., 2010) the title compound crystallized with an aceteontrile solvate molecule.

The central P—N—P angle [142.89 (11)°] is significantly larger than in the corresponding chloride and iodide structures but still falls into the common range for PNP angles in these cations (Lewis et al., 2000). The P-N (1.5775 (17) and 1.5790 (16) Å) and P-C distances (179.4 (2)–180.6 (2) Å) are in the expected range.

Experimental

[(Ph3P)2N]Br has been synthesized from [(Ph3P)2N]Cl and KBr in water according to a literature method (Martinsen et al., 1977). Single crystals suitable for X-ray diffraction were obtained by layering a CH3CN solution with diethyl ether.

Refinement

The hydrogen atoms were positioned geometrically and refined using a riding model. The same Uiso value was used for all H atoms, which refined to 0.0237 (12) Å2.

Figures

Fig. 1.
View of the asymmetric unit of [(Ph3P)2N]Br.CH3CN. Displacement ellipsoids are shown at the 50% probability level and hydrogen atoms are drawn with arbitrary radii.

Crystal data

C36H30NP2+·Br·C2H3NF(000) = 2720
Mr = 659.51Dx = 1.370 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9913 reflections
a = 19.7113 (6) Åθ = 2.4–27.3°
b = 15.9564 (5) ŵ = 1.42 mm1
c = 20.3318 (6) ÅT = 100 K
V = 6394.8 (3) Å3Block, colourless
Z = 80.20 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7749 independent reflections
Radiation source: microfocus sealed tube6140 reflections with I > 2σ(I)
multilayer mirro opticsRint = 0.045
[var phi] and ω scansθmax = 28.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −26→21
Tmin = 0.765, Tmax = 0.805k = −21→20
57718 measured reflectionsl = −25→26

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085Only H-atom displacement parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.0378P)2 + 4.5281P] where P = (Fo2 + 2Fc2)/3
7749 reflections(Δ/σ)max < 0.001
391 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.45 e Å3

Special details

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
P10.25018 (2)0.06051 (3)0.17193 (2)0.01189 (10)
N10.18271 (8)0.01276 (9)0.15375 (7)0.0143 (3)
P20.12559 (2)0.00609 (3)0.09951 (2)0.01196 (10)
C10.28765 (10)0.12141 (11)0.10725 (9)0.0148 (4)
C20.25987 (10)0.19901 (12)0.09087 (9)0.0190 (4)
H20.22530.22280.11760.0236 (11)*
C30.28261 (11)0.24142 (13)0.03571 (11)0.0253 (5)
H30.26280.29350.02380.0236 (11)*
C40.33434 (12)0.20749 (14)−0.00204 (10)0.0285 (5)
H40.35030.2368−0.03970.0236 (11)*
C50.36285 (12)0.13154 (14)0.01468 (10)0.0262 (5)
H50.39900.1095−0.01100.0236 (11)*
C60.33941 (10)0.08711 (12)0.06833 (9)0.0192 (4)
H60.35810.03390.07880.0236 (11)*
C70.23573 (10)0.12855 (11)0.24112 (9)0.0144 (4)
C80.28104 (10)0.19243 (12)0.25734 (10)0.0190 (4)
H80.31850.20410.22940.0236 (11)*
C90.27146 (11)0.23902 (13)0.31445 (10)0.0251 (5)
H90.30200.28300.32530.0236 (11)*
C100.21734 (12)0.22111 (13)0.35532 (10)0.0262 (5)
H100.21170.25170.39500.0236 (11)*
C110.17135 (12)0.15921 (13)0.33905 (10)0.0244 (5)
H110.13360.14860.36690.0236 (11)*
C120.18020 (10)0.11242 (12)0.28210 (9)0.0184 (4)
H120.14870.06960.27100.0236 (11)*
C130.31240 (9)−0.01526 (11)0.19747 (8)0.0131 (4)
C140.37648 (10)0.01108 (12)0.21822 (9)0.0181 (4)
H140.38710.06920.21920.0236 (11)*
C150.42468 (10)−0.04721 (13)0.23733 (9)0.0204 (4)
H150.4683−0.02910.25130.0236 (11)*
C160.40922 (11)−0.13207 (12)0.23604 (9)0.0201 (4)
H160.4424−0.17210.24890.0236 (11)*
C170.34575 (11)−0.15843 (12)0.21612 (10)0.0203 (4)
H170.3352−0.21650.21590.0236 (11)*
C180.29719 (10)−0.10029 (12)0.19634 (9)0.0170 (4)
H180.2538−0.11870.18210.0236 (11)*
C190.08890 (9)−0.09672 (11)0.10613 (9)0.0127 (4)
C200.09094 (10)−0.13784 (11)0.16677 (9)0.0159 (4)
H200.1147−0.11380.20280.0236 (11)*
C210.05793 (10)−0.21417 (12)0.17393 (10)0.0193 (4)
H210.0594−0.24270.21490.0236 (11)*
C220.02288 (10)−0.24900 (12)0.12149 (10)0.0212 (4)
H22−0.0002−0.30080.12700.0236 (11)*
C230.02120 (10)−0.20880 (12)0.06107 (10)0.0204 (4)
H23−0.0025−0.23330.02520.0236 (11)*
C240.05428 (10)−0.13253 (12)0.05318 (9)0.0171 (4)
H240.0533−0.10480.01180.0236 (11)*
C250.05703 (9)0.07942 (12)0.11228 (9)0.0146 (4)
C260.07040 (10)0.16532 (12)0.11015 (10)0.0189 (4)
H260.11490.18450.10040.0236 (11)*
C270.01909 (10)0.22260 (12)0.12217 (9)0.0200 (4)
H270.02850.28100.12070.0236 (11)*
C28−0.04602 (10)0.19508 (12)0.13630 (9)0.0186 (4)
H28−0.08090.23450.14540.0236 (11)*
C29−0.06021 (10)0.10991 (13)0.13709 (9)0.0201 (4)
H29−0.10500.09110.14580.0236 (11)*
C30−0.00886 (10)0.05211 (12)0.12510 (9)0.0168 (4)
H30−0.0187−0.00620.12570.0236 (11)*
C310.15659 (9)0.02082 (11)0.01724 (8)0.0135 (4)
C320.21624 (10)−0.02015 (12)−0.00108 (9)0.0185 (4)
H320.2388−0.05570.02940.0236 (11)*
C330.24261 (11)−0.00892 (13)−0.06364 (9)0.0230 (4)
H330.2834−0.0365−0.07600.0236 (11)*
C340.20953 (11)0.04257 (13)−0.10835 (10)0.0243 (5)
H340.22760.0500−0.15130.0236 (11)*
C350.15028 (11)0.08313 (13)−0.09059 (9)0.0227 (4)
H350.12760.1181−0.12140.0236 (11)*
C360.12382 (10)0.07294 (12)−0.02784 (9)0.0178 (4)
H360.08340.1014−0.01560.0236 (11)*
Br10.115207 (11)0.361552 (13)0.016157 (10)0.02274 (7)
C370.01999 (12)0.99644 (14)0.40311 (11)0.0289 (5)
H37A−0.00501.03500.37440.045 (4)*
H37B0.04601.02870.43550.045 (4)*
H37C−0.01210.95970.42600.045 (4)*
C380.06723 (12)0.94476 (13)0.36271 (9)0.0217 (4)
N20.10065 (10)0.90568 (13)0.33284 (9)0.0323 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0114 (2)0.0112 (2)0.0131 (2)−0.00099 (19)−0.00009 (17)0.00014 (16)
N10.0126 (8)0.0153 (8)0.0150 (8)−0.0022 (6)−0.0023 (6)0.0019 (6)
P20.0114 (2)0.0114 (2)0.0131 (2)−0.00064 (18)−0.00081 (17)0.00066 (16)
C10.0138 (10)0.0147 (9)0.0161 (9)−0.0044 (8)0.0001 (7)−0.0001 (7)
C20.0166 (10)0.0158 (10)0.0245 (10)−0.0016 (8)−0.0001 (8)0.0019 (7)
C30.0261 (12)0.0195 (10)0.0304 (11)−0.0051 (9)−0.0050 (9)0.0084 (8)
C40.0317 (13)0.0328 (12)0.0209 (10)−0.0121 (11)−0.0003 (9)0.0069 (9)
C50.0249 (12)0.0338 (13)0.0199 (11)−0.0031 (10)0.0081 (8)−0.0017 (8)
C60.0201 (11)0.0181 (10)0.0193 (10)−0.0005 (8)0.0007 (8)−0.0029 (7)
C70.0151 (10)0.0133 (9)0.0148 (9)0.0036 (7)−0.0026 (7)−0.0004 (7)
C80.0145 (10)0.0167 (10)0.0257 (10)0.0027 (8)−0.0035 (7)−0.0034 (8)
C90.0236 (11)0.0199 (11)0.0318 (12)0.0072 (9)−0.0122 (9)−0.0096 (8)
C100.0364 (13)0.0244 (11)0.0179 (10)0.0156 (10)−0.0057 (9)−0.0058 (8)
C110.0295 (12)0.0260 (11)0.0177 (10)0.0102 (10)0.0045 (8)0.0033 (8)
C120.0198 (11)0.0170 (9)0.0184 (10)0.0008 (8)0.0029 (7)0.0027 (7)
C130.0132 (9)0.0143 (9)0.0117 (8)0.0018 (7)0.0006 (6)0.0000 (7)
C140.0171 (10)0.0165 (10)0.0208 (10)0.0000 (8)−0.0003 (7)−0.0033 (7)
C150.0140 (10)0.0272 (11)0.0198 (10)0.0009 (9)−0.0026 (7)−0.0036 (8)
C160.0218 (11)0.0209 (10)0.0176 (10)0.0078 (9)−0.0001 (8)0.0007 (7)
C170.0234 (11)0.0141 (9)0.0233 (10)0.0024 (8)0.0005 (8)0.0015 (7)
C180.0149 (10)0.0168 (9)0.0192 (9)−0.0005 (8)0.0005 (7)0.0004 (7)
C190.0094 (9)0.0107 (9)0.0181 (9)0.0005 (7)0.0010 (7)−0.0006 (7)
C200.0119 (9)0.0172 (9)0.0185 (9)0.0011 (8)−0.0006 (7)0.0000 (7)
C210.0157 (10)0.0165 (10)0.0257 (10)0.0027 (8)0.0033 (8)0.0060 (8)
C220.0152 (10)0.0132 (9)0.0353 (11)−0.0010 (8)0.0036 (8)0.0000 (8)
C230.0171 (10)0.0162 (10)0.0279 (11)−0.0007 (8)−0.0036 (8)−0.0048 (8)
C240.0155 (10)0.0168 (9)0.0189 (10)0.0023 (8)−0.0019 (7)−0.0015 (7)
C250.0147 (9)0.0149 (9)0.0142 (9)−0.0001 (8)−0.0011 (7)−0.0003 (7)
C260.0149 (10)0.0165 (9)0.0254 (10)−0.0004 (8)0.0000 (8)0.0005 (7)
C270.0229 (11)0.0128 (9)0.0242 (10)0.0008 (8)−0.0009 (8)−0.0003 (7)
C280.0200 (11)0.0194 (10)0.0165 (9)0.0050 (8)0.0012 (7)0.0003 (7)
C290.0162 (10)0.0231 (10)0.0210 (10)0.0012 (9)0.0038 (8)0.0020 (8)
C300.0171 (10)0.0153 (9)0.0182 (9)−0.0011 (8)0.0014 (7)0.0018 (7)
C310.0132 (9)0.0130 (9)0.0141 (9)−0.0031 (7)−0.0002 (7)−0.0006 (7)
C320.0202 (11)0.0155 (10)0.0197 (9)0.0008 (8)−0.0018 (7)−0.0009 (7)
C330.0232 (11)0.0251 (11)0.0205 (10)−0.0002 (9)0.0051 (8)−0.0075 (8)
C340.0311 (12)0.0271 (11)0.0147 (10)−0.0100 (10)0.0034 (8)−0.0015 (8)
C350.0278 (12)0.0241 (11)0.0163 (10)−0.0072 (9)−0.0061 (8)0.0047 (8)
C360.0155 (10)0.0195 (10)0.0183 (9)−0.0008 (8)−0.0031 (7)0.0028 (7)
Br10.02371 (12)0.02182 (11)0.02270 (11)−0.00315 (9)0.00138 (8)0.00234 (8)
C370.0328 (13)0.0269 (12)0.0270 (11)0.0017 (10)−0.0026 (9)−0.0020 (9)
C380.0340 (13)0.0179 (10)0.0133 (9)−0.0094 (9)−0.0076 (8)0.0045 (8)
N20.0332 (12)0.0361 (11)0.0276 (10)−0.0023 (10)−0.0035 (8)0.0065 (9)

Geometric parameters (Å, °)

P1—N11.5767 (16)C18—H180.9500
P1—C11.7942 (19)C19—C241.397 (3)
P1—C131.7988 (18)C19—C201.397 (3)
P1—C71.7997 (18)C20—C211.389 (3)
N1—P21.5797 (15)C20—H200.9500
P2—C311.7963 (18)C21—C221.387 (3)
P2—C191.7978 (18)C21—H210.9500
P2—C251.8063 (19)C22—C231.386 (3)
C1—C21.394 (3)C22—H220.9500
C1—C61.402 (3)C23—C241.390 (3)
C2—C31.384 (3)C23—H230.9500
C2—H20.9500C24—H240.9500
C3—C41.386 (3)C25—C301.395 (3)
C3—H30.9500C25—C261.396 (3)
C4—C51.378 (3)C26—C271.385 (3)
C4—H40.9500C26—H260.9500
C5—C61.381 (3)C27—C281.387 (3)
C5—H50.9500C27—H270.9500
C6—H60.9500C28—C291.388 (3)
C7—C81.395 (3)C28—H280.9500
C7—C121.399 (3)C29—C301.391 (3)
C8—C91.392 (3)C29—H290.9500
C8—H80.9500C30—H300.9500
C9—C101.382 (3)C31—C321.396 (3)
C9—H90.9500C31—C361.396 (3)
C10—C111.381 (3)C32—C331.386 (3)
C10—H100.9500C32—H320.9500
C11—C121.389 (3)C33—C341.388 (3)
C11—H110.9500C33—H330.9500
C12—H120.9500C34—C351.383 (3)
C13—C181.390 (3)C34—H340.9500
C13—C141.397 (3)C35—C361.388 (3)
C14—C151.385 (3)C35—H350.9500
C14—H140.9500C36—H360.9500
C15—C161.388 (3)C37—C381.491 (3)
C15—H150.9500C37—H37A0.9800
C16—C171.381 (3)C37—H37B0.9800
C16—H160.9500C37—H37C0.9800
C17—C181.392 (3)C38—N21.092 (3)
C17—H170.9500
N1—P1—C1115.92 (8)C13—C18—C17119.83 (18)
N1—P1—C13108.54 (8)C13—C18—H18120.1
C1—P1—C13107.16 (9)C17—C18—H18120.1
N1—P1—C7109.95 (9)C24—C19—C20120.13 (17)
C1—P1—C7108.14 (9)C24—C19—P2120.81 (14)
C13—P1—C7106.72 (8)C20—C19—P2118.88 (14)
P1—N1—P2142.88 (10)C21—C20—C19119.40 (18)
N1—P2—C31113.51 (8)C21—C20—H20120.3
N1—P2—C19107.22 (8)C19—C20—H20120.3
C31—P2—C19109.03 (8)C22—C21—C20120.29 (18)
N1—P2—C25112.90 (8)C22—C21—H21119.9
C31—P2—C25107.67 (8)C20—C21—H21119.9
C19—P2—C25106.22 (9)C23—C22—C21120.52 (19)
C2—C1—C6119.84 (17)C23—C22—H22119.7
C2—C1—P1119.63 (14)C21—C22—H22119.7
C6—C1—P1120.11 (14)C22—C23—C24119.75 (18)
C3—C2—C1120.03 (19)C22—C23—H23120.1
C3—C2—H2120.0C24—C23—H23120.1
C1—C2—H2120.0C23—C24—C19119.90 (18)
C2—C3—C4119.7 (2)C23—C24—H24120.1
C2—C3—H3120.1C19—C24—H24120.1
C4—C3—H3120.1C30—C25—C26119.23 (18)
C5—C4—C3120.44 (19)C30—C25—P2121.42 (14)
C5—C4—H4119.8C26—C25—P2119.35 (14)
C3—C4—H4119.8C27—C26—C25120.30 (18)
C4—C5—C6120.7 (2)C27—C26—H26119.9
C4—C5—H5119.7C25—C26—H26119.9
C6—C5—H5119.7C26—C27—C28120.23 (18)
C5—C6—C1119.27 (19)C26—C27—H27119.9
C5—C6—H6120.4C28—C27—H27119.9
C1—C6—H6120.4C27—C28—C29119.95 (18)
C8—C7—C12119.63 (17)C27—C28—H28120.0
C8—C7—P1121.62 (15)C29—C28—H28120.0
C12—C7—P1118.57 (14)C28—C29—C30120.05 (19)
C9—C8—C7120.05 (19)C28—C29—H29120.0
C9—C8—H8120.0C30—C29—H29120.0
C7—C8—H8120.0C29—C30—C25120.22 (18)
C10—C9—C8119.7 (2)C29—C30—H30119.9
C10—C9—H9120.1C25—C30—H30119.9
C8—C9—H9120.1C32—C31—C36119.58 (17)
C11—C10—C9120.70 (19)C32—C31—P2118.27 (14)
C11—C10—H10119.6C36—C31—P2122.13 (15)
C9—C10—H10119.6C33—C32—C31120.02 (18)
C10—C11—C12120.1 (2)C33—C32—H32120.0
C10—C11—H11119.9C31—C32—H32120.0
C12—C11—H11119.9C32—C33—C34120.1 (2)
C11—C12—C7119.72 (19)C32—C33—H33120.0
C11—C12—H12120.1C34—C33—H33120.0
C7—C12—H12120.1C35—C34—C33120.18 (18)
C18—C13—C14119.61 (17)C35—C34—H34119.9
C18—C13—P1120.29 (14)C33—C34—H34119.9
C14—C13—P1120.10 (14)C34—C35—C36120.16 (19)
C15—C14—C13120.20 (18)C34—C35—H35119.9
C15—C14—H14119.9C36—C35—H35119.9
C13—C14—H14119.9C35—C36—C31119.96 (19)
C14—C15—C16119.94 (19)C35—C36—H36120.0
C14—C15—H15120.0C31—C36—H36120.0
C16—C15—H15120.0C38—C37—H37A109.5
C17—C16—C15120.11 (19)C38—C37—H37B109.5
C17—C16—H16119.9H37A—C37—H37B109.5
C15—C16—H16119.9C38—C37—H37C109.5
C16—C17—C18120.31 (18)H37A—C37—H37C109.5
C16—C17—H17119.8H37B—C37—H37C109.5
C18—C17—H17119.8N2—C38—C37178.4 (2)
C1—P1—N1—P2−12.2 (2)C14—C13—C18—C170.3 (3)
C13—P1—N1—P2−132.79 (17)P1—C13—C18—C17179.90 (14)
C7—P1—N1—P2110.82 (18)C16—C17—C18—C13−0.8 (3)
P1—N1—P2—C3135.6 (2)N1—P2—C19—C24−158.31 (15)
P1—N1—P2—C19156.03 (17)C31—P2—C19—C24−35.04 (18)
P1—N1—P2—C25−87.33 (19)C25—P2—C19—C2480.74 (16)
N1—P1—C1—C277.13 (17)N1—P2—C19—C2026.59 (17)
C13—P1—C1—C2−161.53 (15)C31—P2—C19—C20149.86 (15)
C7—P1—C1—C2−46.83 (17)C25—P2—C19—C20−94.37 (16)
N1—P1—C1—C6−95.43 (17)C24—C19—C20—C21−0.4 (3)
C13—P1—C1—C625.91 (18)P2—C19—C20—C21174.72 (14)
C7—P1—C1—C6140.62 (15)C19—C20—C21—C22−0.4 (3)
C6—C1—C2—C31.0 (3)C20—C21—C22—C231.0 (3)
P1—C1—C2—C3−171.53 (16)C21—C22—C23—C24−0.7 (3)
C1—C2—C3—C4−1.8 (3)C22—C23—C24—C19−0.1 (3)
C2—C3—C4—C50.6 (3)C20—C19—C24—C230.7 (3)
C3—C4—C5—C61.5 (3)P2—C19—C24—C23−174.36 (15)
C4—C5—C6—C1−2.2 (3)N1—P2—C25—C30−116.56 (16)
C2—C1—C6—C50.9 (3)C31—P2—C25—C30117.35 (16)
P1—C1—C6—C5173.48 (16)C19—P2—C25—C300.67 (17)
N1—P1—C7—C8−164.10 (15)N1—P2—C25—C2662.58 (17)
C1—P1—C7—C8−36.63 (18)C31—P2—C25—C26−63.51 (17)
C13—P1—C7—C878.37 (17)C19—P2—C25—C26179.81 (15)
N1—P1—C7—C1220.69 (17)C30—C25—C26—C271.5 (3)
C1—P1—C7—C12148.16 (15)P2—C25—C26—C27−177.65 (15)
C13—P1—C7—C12−96.84 (16)C25—C26—C27—C28−0.1 (3)
C12—C7—C8—C90.9 (3)C26—C27—C28—C29−1.3 (3)
P1—C7—C8—C9−174.29 (15)C27—C28—C29—C301.4 (3)
C7—C8—C9—C100.7 (3)C28—C29—C30—C250.0 (3)
C8—C9—C10—C11−2.1 (3)C26—C25—C30—C29−1.5 (3)
C9—C10—C11—C121.9 (3)P2—C25—C30—C29177.68 (14)
C10—C11—C12—C7−0.3 (3)N1—P2—C31—C3244.97 (17)
C8—C7—C12—C11−1.1 (3)C19—P2—C31—C32−74.47 (16)
P1—C7—C12—C11174.25 (15)C25—P2—C31—C32170.70 (14)
N1—P1—C13—C182.28 (17)N1—P2—C31—C36−133.64 (16)
C1—P1—C13—C18−123.61 (15)C19—P2—C31—C36106.93 (16)
C7—P1—C13—C18120.73 (15)C25—P2—C31—C36−7.91 (18)
N1—P1—C13—C14−178.09 (14)C36—C31—C32—C330.1 (3)
C1—P1—C13—C1456.02 (17)P2—C31—C32—C33−178.58 (15)
C7—P1—C13—C14−59.64 (17)C31—C32—C33—C34−0.5 (3)
C18—C13—C14—C150.2 (3)C32—C33—C34—C350.2 (3)
P1—C13—C14—C15−179.39 (14)C33—C34—C35—C360.4 (3)
C13—C14—C15—C16−0.2 (3)C34—C35—C36—C31−0.8 (3)
C14—C15—C16—C17−0.4 (3)C32—C31—C36—C350.6 (3)
C15—C16—C17—C180.9 (3)P2—C31—C36—C35179.15 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FI2100).

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