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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1431.
Published online 2009 May 29. doi:  10.1107/S1600536809019254
PMCID: PMC2969812

A second monoclinic modification of triphenyl­phosphine oxide hemihydrate

Abstract

In the crystal of the title compound, C18H15OP·0.5H2O, a water molecule links to two adjacent triphenylphosphine molecules by way of O—H(...)O hydrogen bonds. The crystal is twinned, the minor twin component being 36%.

Related literature

For the C2/c modification, see: Baures (1991 [triangle]). For the Fdd2 modification, see: Baures & Silverton (1990 [triangle]) (the authors mention a Cc modification without providing details).

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Object name is e-65-o1431-scheme1.jpg

Experimental

Crystal data

  • C18H15OP·0.5H2O
  • M r = 287.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1431-efi1.jpg
  • a = 9.4313 (1) Å
  • b = 32.1930 (4) Å
  • c = 10.8435 (1) Å
  • β = 115.742 (1)°
  • V = 2965.59 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.947, T max = 0.965
  • 14206 measured reflections
  • 6609 independent reflections
  • 6504 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.065
  • S = 1.02
  • 6609 reflections
  • 379 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.17 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3203 Friedel pairs
  • Flack parameter: 0.02 (5)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019254/xu2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019254/xu2526Isup2.hkl

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

Acknowledgments

The author thanks the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The compound was the unexpected crystalline product of the reaction between tetracyclohexyltin (1 g, 2.2 mmol) and dibromotriphenylphosphine (1 g, 2.4 mmol) in ethanol. The reactants were heated in the solvent for an hour. The solvent was allowed to evaporate to leave behind a mixture of crystalline products. The product probably resulted from the hydrolysis of the phosphine.

Refinement

The carbon-bound H-atoms were generated geometrically (C—H 0.95 Å) and were allowed to ride on their parent atoms, with U(H) fixed at 1.2Ueq(C). The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H 0.84±0.01 Å; temperature factors were freely refined.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level, and hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

Crystal data

C18H15OP·0.5H2OF(000) = 1208
Mr = 287.28Dx = 1.287 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 9366 reflections
a = 9.4313 (1) Åθ = 2.4–28.2°
b = 32.1930 (4) ŵ = 0.18 mm1
c = 10.8435 (1) ÅT = 100 K
β = 115.742 (1)°Block, colorless
V = 2965.59 (6) Å30.30 × 0.25 × 0.20 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer6609 independent reflections
Radiation source: fine-focus sealed tube6504 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.947, Tmax = 0.965k = −41→41
14206 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6609 reflectionsΔρmax = 0.24 e Å3
379 parametersΔρmin = −0.17 e Å3
4 restraintsAbsolute structure: Flack (1983), 3203 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
P10.50187 (5)0.437805 (13)0.50006 (5)0.01863 (12)
P20.27142 (5)0.309772 (14)−0.01509 (4)0.01939 (12)
O10.39737 (18)0.40302 (4)0.42266 (15)0.0290 (3)
O20.2633 (2)0.34385 (4)0.07577 (16)0.0313 (3)
O1W0.1024 (2)0.37124 (8)0.2330 (2)0.0539 (5)
H10.189 (3)0.3741 (11)0.301 (3)0.090 (14)*
H20.126 (4)0.3598 (9)0.176 (3)0.062 (10)*
C10.6506 (2)0.44805 (6)0.4419 (2)0.0233 (4)
C20.6694 (3)0.41888 (7)0.3542 (2)0.0324 (5)
H2A0.60440.39490.32720.039*
C30.7822 (3)0.42496 (8)0.3069 (3)0.0454 (7)
H30.79410.40540.24660.055*
C40.8776 (3)0.45964 (9)0.3476 (3)0.0485 (7)
H40.95560.46360.31540.058*
C50.8609 (3)0.48886 (8)0.4353 (3)0.0407 (6)
H50.92750.51250.46330.049*
C60.7458 (2)0.48303 (7)0.4817 (2)0.0303 (5)
H60.73250.50300.54050.036*
C70.3943 (2)0.48571 (5)0.4777 (2)0.0211 (4)
C80.2742 (2)0.49264 (7)0.3473 (2)0.0281 (5)
H80.24880.47190.27870.034*
C90.1909 (3)0.53010 (7)0.3171 (3)0.0344 (5)
H90.11070.53520.22770.041*
C100.2272 (3)0.55987 (6)0.4198 (3)0.0334 (6)
H100.17160.58550.40000.040*
C110.3420 (3)0.55246 (7)0.5488 (3)0.0313 (5)
H110.36360.57270.61830.038*
C120.4276 (3)0.51563 (6)0.5793 (2)0.0263 (4)
H120.50810.51090.66890.032*
C130.6082 (2)0.42669 (6)0.6805 (2)0.0189 (4)
C140.5294 (2)0.42678 (6)0.7640 (2)0.0245 (4)
H140.42330.43600.72820.029*
C150.6055 (3)0.41348 (7)0.8986 (2)0.0283 (4)
H150.55180.41390.95510.034*
C160.7600 (3)0.39947 (7)0.9512 (2)0.0303 (5)
H160.81180.39031.04340.036*
C170.8380 (2)0.39900 (7)0.8685 (2)0.0280 (5)
H170.94340.38920.90450.034*
C180.7640 (2)0.41266 (6)0.7337 (2)0.0238 (4)
H180.81880.41250.67800.029*
C190.4727 (2)0.29581 (6)0.02612 (19)0.0229 (4)
C200.5931 (3)0.32190 (7)0.1102 (2)0.0350 (5)
H200.57020.34630.14760.042*
C210.7491 (3)0.31176 (9)0.1393 (3)0.0490 (7)
H210.83260.32930.19710.059*
C220.7812 (3)0.27687 (9)0.0848 (3)0.0532 (8)
H220.88730.27060.10440.064*
C230.6632 (3)0.25051 (8)0.0020 (3)0.0454 (6)
H230.68750.2261−0.03410.054*
C240.5076 (2)0.26023 (6)−0.0279 (2)0.0294 (5)
H240.42500.2424−0.08550.035*
C250.1779 (2)0.26268 (5)0.0024 (2)0.0205 (3)
C260.1924 (2)0.25324 (6)0.1333 (2)0.0248 (4)
H260.24390.27210.20680.030*
C270.1310 (2)0.21616 (6)0.1556 (2)0.0288 (4)
H270.14190.20960.24480.035*
C280.0546 (3)0.18885 (6)0.0493 (3)0.0288 (5)
H280.01320.16360.06560.035*
C290.0377 (2)0.19808 (6)−0.0821 (2)0.0249 (4)
H29−0.01670.1794−0.15550.030*
C300.1007 (2)0.23465 (6)−0.1051 (2)0.0230 (4)
H300.09150.2407−0.19410.028*
C310.1855 (2)0.32405 (6)−0.1932 (2)0.0202 (4)
C320.0223 (2)0.32522 (6)−0.2683 (2)0.0245 (4)
H32−0.04360.3158−0.22820.029*
C33−0.0444 (3)0.34019 (7)−0.4020 (3)0.0297 (5)
H33−0.15550.3407−0.45340.036*
C340.0521 (3)0.35441 (7)−0.4601 (2)0.0283 (4)
H340.00630.3647−0.55120.034*
C350.2138 (2)0.35372 (6)−0.3869 (2)0.0249 (4)
H350.27910.3636−0.42700.030*
C360.2802 (2)0.33844 (6)−0.2535 (2)0.0225 (4)
H360.39150.3378−0.20280.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0212 (3)0.0158 (2)0.0184 (2)0.00008 (17)0.00812 (19)−0.00098 (18)
P20.0238 (3)0.0167 (2)0.0194 (3)−0.00428 (18)0.0110 (2)−0.00323 (18)
O10.0326 (8)0.0215 (6)0.0255 (7)−0.0022 (6)0.0056 (6)−0.0038 (6)
O20.0468 (9)0.0238 (7)0.0302 (8)−0.0088 (6)0.0232 (7)−0.0084 (6)
O1W0.0235 (9)0.0977 (15)0.0408 (9)−0.0137 (10)0.0144 (9)−0.0238 (10)
C10.0262 (9)0.0265 (9)0.0214 (9)0.0102 (7)0.0143 (8)0.0097 (7)
C20.0457 (13)0.0306 (10)0.0247 (10)0.0165 (10)0.0188 (10)0.0090 (8)
C30.0653 (17)0.0488 (15)0.0371 (13)0.0314 (13)0.0361 (13)0.0198 (12)
C40.0477 (15)0.0674 (17)0.0475 (15)0.0333 (14)0.0365 (13)0.0341 (14)
C50.0314 (11)0.0453 (13)0.0510 (15)0.0066 (10)0.0231 (11)0.0226 (12)
C60.0300 (12)0.0303 (10)0.0333 (11)0.0069 (8)0.0162 (10)0.0107 (9)
C70.0211 (9)0.0156 (8)0.0291 (10)0.0009 (6)0.0131 (9)0.0010 (8)
C80.0241 (10)0.0280 (10)0.0312 (11)0.0055 (8)0.0111 (9)0.0009 (8)
C90.0243 (10)0.0346 (11)0.0415 (13)0.0065 (9)0.0115 (10)0.0091 (10)
C100.0275 (12)0.0197 (10)0.0591 (16)0.0041 (8)0.0244 (11)0.0075 (9)
C110.0319 (11)0.0197 (9)0.0502 (14)−0.0025 (8)0.0251 (11)−0.0055 (9)
C120.0299 (10)0.0210 (9)0.0299 (11)−0.0030 (8)0.0148 (9)−0.0021 (8)
C130.0222 (9)0.0155 (8)0.0180 (9)−0.0035 (7)0.0076 (8)−0.0010 (7)
C140.0238 (9)0.0262 (10)0.0264 (10)0.0004 (7)0.0135 (8)−0.0015 (8)
C150.0323 (11)0.0327 (11)0.0280 (10)−0.0014 (9)0.0208 (9)0.0013 (9)
C160.0342 (11)0.0332 (10)0.0226 (10)−0.0014 (9)0.0116 (9)0.0028 (8)
C170.0187 (9)0.0354 (11)0.0277 (11)−0.0024 (8)0.0080 (8)0.0028 (9)
C180.0232 (9)0.0280 (10)0.0240 (10)0.0002 (8)0.0138 (8)0.0039 (8)
C190.0184 (8)0.0265 (9)0.0196 (9)−0.0039 (7)0.0045 (7)0.0076 (7)
C200.0317 (12)0.0351 (11)0.0275 (11)−0.0132 (9)0.0031 (10)0.0088 (9)
C210.0240 (11)0.0537 (16)0.0466 (15)−0.0151 (11)−0.0058 (11)0.0241 (12)
C220.0243 (11)0.0564 (16)0.0723 (19)0.0065 (11)0.0148 (12)0.0419 (15)
C230.0337 (12)0.0396 (12)0.0683 (17)0.0134 (10)0.0273 (13)0.0277 (13)
C240.0249 (10)0.0292 (10)0.0341 (12)0.0042 (8)0.0129 (9)0.0092 (8)
C250.0193 (9)0.0191 (8)0.0232 (9)−0.0012 (7)0.0094 (8)−0.0006 (8)
C260.0221 (9)0.0283 (10)0.0254 (10)−0.0014 (8)0.0117 (8)0.0001 (8)
C270.0290 (10)0.0292 (10)0.0339 (11)−0.0009 (9)0.0191 (9)0.0036 (9)
C280.0217 (10)0.0204 (10)0.0475 (14)0.0015 (7)0.0179 (9)0.0040 (8)
C290.0204 (9)0.0186 (9)0.0322 (11)0.0001 (7)0.0082 (8)−0.0022 (8)
C300.0222 (9)0.0203 (9)0.0245 (10)0.0034 (7)0.0082 (8)−0.0010 (8)
C310.0218 (9)0.0156 (8)0.0213 (10)0.0012 (7)0.0076 (8)−0.0012 (8)
C320.0207 (9)0.0230 (10)0.0314 (11)−0.0001 (7)0.0128 (8)−0.0013 (8)
C330.0195 (9)0.0297 (10)0.0326 (11)0.0015 (8)0.0045 (9)0.0017 (9)
C340.0304 (10)0.0293 (10)0.0214 (10)0.0038 (8)0.0076 (9)0.0057 (8)
C350.0269 (10)0.0268 (9)0.0234 (10)0.0010 (8)0.0131 (9)0.0035 (8)
C360.0191 (9)0.0235 (9)0.0246 (10)−0.0007 (7)0.0093 (8)−0.0011 (8)

Geometric parameters (Å, °)

P1—O11.4871 (15)C16—C171.385 (3)
P1—C11.801 (2)C16—H160.9500
P1—C71.8035 (18)C17—C181.390 (3)
P1—C131.805 (2)C17—H170.9500
P2—O21.4985 (14)C18—H180.9500
P2—C311.799 (2)C19—C201.388 (3)
P2—C251.8051 (19)C19—C241.390 (3)
P2—C191.8076 (19)C20—C211.402 (4)
O1W—H10.84 (3)C20—H200.9500
O1W—H20.83 (3)C21—C221.363 (4)
C1—C61.387 (3)C21—H210.9500
C1—C21.401 (3)C22—C231.377 (4)
C2—C31.381 (4)C22—H220.9500
C2—H2A0.9500C23—C241.394 (3)
C3—C41.381 (4)C23—H230.9500
C3—H30.9500C24—H240.9500
C4—C51.395 (4)C25—C261.399 (3)
C4—H40.9500C25—C301.402 (3)
C5—C61.394 (3)C26—C271.393 (3)
C5—H50.9500C26—H260.9500
C6—H60.9500C27—C281.378 (3)
C7—C121.393 (3)C27—H270.9500
C7—C81.394 (3)C28—C291.395 (3)
C8—C91.398 (3)C28—H280.9500
C8—H80.9500C29—C301.389 (3)
C9—C101.395 (4)C29—H290.9500
C9—H90.9500C30—H300.9500
C10—C111.367 (4)C31—C321.395 (3)
C10—H100.9500C31—C361.395 (3)
C11—C121.391 (3)C32—C331.392 (3)
C11—H110.9500C32—H320.9500
C12—H120.9500C33—C341.390 (3)
C13—C141.398 (3)C33—H330.9500
C13—C181.400 (3)C34—C351.379 (3)
C14—C151.385 (3)C34—H340.9500
C14—H140.9500C35—C361.393 (3)
C15—C161.389 (3)C35—H350.9500
C15—H150.9500C36—H360.9500
O1—P1—C1111.49 (10)C16—C17—C18120.80 (19)
O1—P1—C7111.83 (9)C16—C17—H17119.6
C1—P1—C7105.96 (9)C18—C17—H17119.6
O1—P1—C13112.48 (9)C17—C18—C13119.51 (18)
C1—P1—C13105.40 (9)C17—C18—H18120.2
C7—P1—C13109.28 (9)C13—C18—H18120.2
O2—P2—C31113.00 (9)C20—C19—C24119.9 (2)
O2—P2—C25112.26 (9)C20—C19—P2118.93 (17)
C31—P2—C25108.33 (9)C24—C19—P2121.10 (15)
O2—P2—C19111.57 (10)C19—C20—C21119.1 (2)
C31—P2—C19105.30 (9)C19—C20—H20120.5
C25—P2—C19105.90 (9)C21—C20—H20120.5
H1—O1W—H2104 (3)C22—C21—C20120.2 (2)
C6—C1—C2120.0 (2)C22—C21—H21119.9
C6—C1—P1122.44 (15)C20—C21—H21119.9
C2—C1—P1117.53 (17)C21—C22—C23121.4 (2)
C3—C2—C1120.1 (2)C21—C22—H22119.3
C3—C2—H2A119.9C23—C22—H22119.3
C1—C2—H2A119.9C22—C23—C24119.0 (3)
C4—C3—C2119.8 (2)C22—C23—H23120.5
C4—C3—H3120.1C24—C23—H23120.5
C2—C3—H3120.1C19—C24—C23120.4 (2)
C3—C4—C5120.8 (2)C19—C24—H24119.8
C3—C4—H4119.6C23—C24—H24119.8
C5—C4—H4119.6C26—C25—C30119.38 (18)
C6—C5—C4119.5 (2)C26—C25—P2116.88 (15)
C6—C5—H5120.3C30—C25—P2123.64 (16)
C4—C5—H5120.3C27—C26—C25119.83 (19)
C1—C6—C5119.8 (2)C27—C26—H26120.1
C1—C6—H6120.1C25—C26—H26120.1
C5—C6—H6120.1C28—C27—C26120.5 (2)
C12—C7—C8119.78 (18)C28—C27—H27119.8
C12—C7—P1124.40 (16)C26—C27—H27119.8
C8—C7—P1115.79 (16)C27—C28—C29120.29 (19)
C7—C8—C9120.1 (2)C27—C28—H28119.9
C7—C8—H8119.9C29—C28—H28119.9
C9—C8—H8119.9C30—C29—C28119.7 (2)
C10—C9—C8119.2 (2)C30—C29—H29120.1
C10—C9—H9120.4C28—C29—H29120.1
C8—C9—H9120.4C29—C30—C25120.2 (2)
C11—C10—C9120.5 (2)C29—C30—H30119.9
C11—C10—H10119.8C25—C30—H30119.9
C9—C10—H10119.8C32—C31—C36119.09 (18)
C10—C11—C12120.8 (2)C32—C31—P2120.15 (16)
C10—C11—H11119.6C36—C31—P2120.39 (15)
C12—C11—H11119.6C33—C32—C31120.15 (19)
C11—C12—C7119.5 (2)C33—C32—H32119.9
C11—C12—H12120.2C31—C32—H32119.9
C7—C12—H12120.2C34—C33—C32119.85 (19)
C14—C13—C18119.49 (18)C34—C33—H33120.1
C14—C13—P1120.00 (15)C32—C33—H33120.1
C18—C13—P1119.98 (15)C35—C34—C33120.7 (2)
C15—C14—C13120.22 (18)C35—C34—H34119.6
C15—C14—H14119.9C33—C34—H34119.6
C13—C14—H14119.9C34—C35—C36119.32 (19)
C14—C15—C16120.29 (19)C34—C35—H35120.3
C14—C15—H15119.9C36—C35—H35120.3
C16—C15—H15119.9C35—C36—C31120.85 (18)
C17—C16—C15119.7 (2)C35—C36—H36119.6
C17—C16—H16120.2C31—C36—H36119.6
C15—C16—H16120.2
O1—P1—C1—C6169.22 (16)O2—P2—C19—C20−13.47 (18)
C7—P1—C1—C647.3 (2)C31—P2—C19—C20109.47 (17)
C13—P1—C1—C6−68.45 (18)C25—P2—C19—C20−135.89 (16)
O1—P1—C1—C2−11.38 (19)O2—P2—C19—C24168.31 (15)
C7—P1—C1—C2−133.27 (16)C31—P2—C19—C24−68.75 (17)
C13—P1—C1—C2110.95 (17)C25—P2—C19—C2445.89 (19)
C6—C1—C2—C3−0.2 (3)C24—C19—C20—C210.0 (3)
P1—C1—C2—C3−179.65 (16)P2—C19—C20—C21−178.23 (18)
C1—C2—C3—C40.8 (3)C19—C20—C21—C220.4 (3)
C2—C3—C4—C5−0.4 (4)C20—C21—C22—C23−0.9 (4)
C3—C4—C5—C6−0.4 (3)C21—C22—C23—C240.9 (4)
C2—C1—C6—C5−0.6 (3)C20—C19—C24—C230.1 (3)
P1—C1—C6—C5178.78 (16)P2—C19—C24—C23178.29 (18)
C4—C5—C6—C10.9 (3)C22—C23—C24—C19−0.6 (4)
O1—P1—C7—C12144.49 (16)O2—P2—C25—C26−35.86 (18)
C1—P1—C7—C12−93.83 (18)C31—P2—C25—C26−161.33 (15)
C13—P1—C7—C1219.28 (19)C19—P2—C25—C2686.12 (16)
O1—P1—C7—C8−37.70 (19)O2—P2—C25—C30147.75 (16)
C1—P1—C7—C883.97 (17)C31—P2—C25—C3022.27 (18)
C13—P1—C7—C8−162.91 (15)C19—P2—C25—C30−90.28 (17)
C12—C7—C8—C92.2 (3)C30—C25—C26—C270.3 (3)
P1—C7—C8—C9−175.69 (16)P2—C25—C26—C27−176.21 (15)
C7—C8—C9—C10−1.5 (3)C25—C26—C27—C28−0.7 (3)
C8—C9—C10—C11−0.4 (3)C26—C27—C28—C290.0 (3)
C9—C10—C11—C121.6 (3)C27—C28—C29—C301.1 (3)
C10—C11—C12—C7−0.9 (3)C28—C29—C30—C25−1.5 (3)
C8—C7—C12—C11−1.0 (3)C26—C25—C30—C290.7 (3)
P1—C7—C12—C11176.70 (16)P2—C25—C30—C29177.05 (15)
O1—P1—C13—C14−73.10 (19)O2—P2—C31—C32−76.16 (18)
C1—P1—C13—C14165.21 (16)C25—P2—C31—C3248.88 (18)
C7—P1—C13—C1451.73 (19)C19—P2—C31—C32161.83 (16)
O1—P1—C13—C1898.50 (17)O2—P2—C31—C3696.75 (17)
C1—P1—C13—C18−23.18 (19)C25—P2—C31—C36−138.21 (16)
C7—P1—C13—C18−136.67 (16)C19—P2—C31—C36−25.27 (18)
C18—C13—C14—C150.6 (3)C36—C31—C32—C330.6 (3)
P1—C13—C14—C15172.26 (16)P2—C31—C32—C33173.60 (16)
C13—C14—C15—C16−0.8 (3)C31—C32—C33—C34−0.7 (3)
C14—C15—C16—C170.2 (3)C32—C33—C34—C350.2 (3)
C15—C16—C17—C180.5 (3)C33—C34—C35—C360.2 (3)
C16—C17—C18—C13−0.6 (3)C34—C35—C36—C31−0.3 (3)
C14—C13—C18—C170.1 (3)C32—C31—C36—C35−0.1 (3)
P1—C13—C18—C17−171.57 (16)P2—C31—C36—C35−173.12 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H1···O10.84 (3)2.05 (2)2.836 (2)156 (4)
O1w—H2···O20.83 (3)2.09 (2)2.870 (2)158 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2526).

References

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