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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o256.
Published online 2007 December 12. doi:  10.1107/S1600536807064343
PMCID: PMC2915313

1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate

Abstract

The title compound, racemic bnppa, C20H13O4P, crystallizes with four mol­ecules in the asymmetric unit. Two independent centrosymmetric O—H(...)O hydrogen-bonded tetra­mers, each involving two of the symmetry-independent mol­ecules in the asymmetric unit generate the packing motif in the crystal structure. The hydro­phobic parts of the tetra­mers connect to their neighbours via C—H(...)π and π–π inter­actions [3.899 (2), 3.895 (2) and 3.803 (2) Å within the symmetric unit, 3.851 (2), 4.000 (2), 3.988 (2) and 3.905 (2) Å across centres of symmetry].

Related literature

For details on bnppa as an optical resolution agent of amines, see: Fujii & Hirayamma (2002 [triangle]); Arnold et al. (1983 [triangle]); Wilen et al. (1991 [triangle]). For the conglomerate nature of racemates, see: Jacques et al. (1981 [triangle]). For related literature, see: An et al. (1996 [triangle]); Bernstein et al. (1995 [triangle]); Etter & Baures (1988 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o256-scheme1.jpg

Experimental

Crystal data

  • C20H13O4P
  • M r = 348.27
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o256-efi1.jpg
  • a = 14.2152 (14) Å
  • b = 14.6480 (14) Å
  • c = 15.6397 (15) Å
  • α = 87.710 (2)°
  • β = 88.074 (2)°
  • γ = 83.952 (2)°
  • V = 3234.4 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 292 (2) K
  • 0.31 × 0.07 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.939, T max = 0.989
  • 32848 measured reflections
  • 12219 independent reflections
  • 7419 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.160
  • S = 1.06
  • 12219 reflections
  • 901 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: WinGX (Farrugia, 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 [triangle]) and CAMERON (Watkin et al., 1993 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064343/ln2013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064343/ln2013Isup2.hkl

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

Acknowledgments

The authors thank DST-IRHPA for the CCD X-ray facility at IISc and CSIR (SRF), India, for financial support.

supplementary crystallographic information

Comment

We have been investigating the conglomerate nature of racemates in our laboratory, as very few structures show the features of conglomerates (Jacques et al., 1981). Optically active 1,1'-binaphthalene-2,2'-diyl hydrogen phosphate (bnppa) has been used as a good optical resolution agent for amines (Fujii et al., 2002; Arnold et al., 1983; Wilen et al., 1991). However, the procedure adopted in the preparation yields only racemic bnppa crystals (Scheme).

The compound crystallizes in a triclinic space group P-1, with Z = 8. Of the four molecules in the asymmetric unit (Fig. 1), pairs are connected through intermolecular O—H···O hydrogen bonds (Table 1) and two such motifs form independent centrosymmetric tetramers (Fig. 2) though additional O—H···O hydrogen bonds. The packing in the crystal structure is hence through tetrameric O—H···O hydrogen bonded systems [Etter's graph set symbol R44(16)] (Bernstein et al., 1995). Further, the hydrophobic parts of the symmetry-independent parts of the tetramers are linked via C—H···π interactions [C27—H27···π (C64/C65/C66/C67/C68/C69) = 2.75 Å, C54—H54···π (C12/C13/C14/C14/C15/C16/C17 = 2.77 Å)]. There are several π···π interactions within the symmetric unit [3.899 (2), 3.895 (2) and 3.803 (2) Å], as well as others across centres of symmetry [3.851 (2), 4.000 (2), 3.988 (2) and 3.905 (2) Å]. Table 1 lists all O—H···0 hydrogen bonds along with two C—H..O interactions which form as a consequence of tetramer formation.

Experimental

Racemic binaphthylphosphoylchloride (29.2 g, 80 mmol) prepared by a known procedure (An et al., 1996) was dissolved in 1.4 l. of 2% Na2CO3 solution and heated until a clear solution formed. The solution, on keeping at 273 K for 12 h, yields a grey precipitate. The precipitate was collected by filtration, washed with 100 ml of 2% Na2CO3 solution and suspended in 650 ml of water. 50 ml of conc. HCl was then added to this while stirring. The mixture was heated to 368 K for 5 minutes and was kept at 277 K for 14 h. The resulting white crystalline mass was separated by filtration followed by washing with cold water and dried to obtain bnppa in 59.2% yield (m.p. 621 K). Plate-like colourless crystals of bnppa were grown in acetonitrile and water (2:1 v/v) with triphenyphosphine oxide as an additive promotor in the ratio 50:50 (Etter et al., 1988) by slow evaporation at room temperature.

Refinement

All H atoms were positioned geometrically, (C—H = 0.93 Å, O—H = 0.82 Å) and refined using a riding model with Uiso(H)= 1.2 Ueq(C) or 1.5 Ueq(O).

Figures

Fig. 1.
The four molecules in the asymmetric unit with O—H···O hydrogen bonds and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
Fig. 2.
The molecular packing showing the O—H···O hydrogen bonds which create tetramers with the R44(16) motif.

Crystal data

C20H13O4PZ = 8
Mr = 348.27F000 = 1440
Triclinic, P1Dx = 1.430 Mg m3
Hall symbol: -P 1Melting point: 348 K
a = 14.2152 (14) ÅMo Kα radiation λ = 0.71073 Å
b = 14.6480 (14) ÅCell parameters from 640 reflections
c = 15.6397 (15) Åθ = 0.9–28.0º
α = 87.710 (2)ºµ = 0.19 mm1
β = 88.074 (2)ºT = 292 (2) K
γ = 83.952 (2)ºNeedle, colourless
V = 3234.4 (5) Å30.31 × 0.07 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer12219 independent reflections
Radiation source: fine-focus sealed tube7419 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.053
T = 292(2) Kθmax = 25.7º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.939, Tmax = 0.989k = −17→17
32848 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.160  w = 1/[σ2(Fo2) + (0.0616P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
12219 reflectionsΔρmax = 0.31 e Å3
901 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
P10.18879 (7)0.59609 (7)0.09812 (7)0.0433 (3)
P20.02314 (7)0.32601 (7)0.13354 (7)0.0414 (3)
P30.94345 (8)0.64658 (7)0.34851 (7)0.0479 (3)
P40.80353 (7)0.37386 (7)0.44392 (7)0.0434 (3)
O10.18978 (16)0.63722 (16)0.18932 (15)0.0429 (6)
O20.28908 (16)0.61002 (16)0.05549 (14)0.0413 (6)
O30.10800 (18)0.6437 (2)0.05428 (18)0.0664 (8)
O40.19492 (18)0.49120 (17)0.10530 (17)0.0569 (8)
H1O0.14830.47560.13200.085*
O5−0.00382 (16)0.30050 (15)0.22946 (15)0.0414 (6)
O60.11649 (17)0.26132 (16)0.11331 (15)0.0428 (6)
O70.04349 (17)0.42177 (16)0.11774 (17)0.0534 (7)
O8−0.06052 (18)0.29605 (18)0.08799 (17)0.0593 (8)
H2O−0.05150.30170.03610.089*
O90.85273 (18)0.71325 (15)0.37247 (15)0.0456 (7)
O100.97501 (16)0.67963 (16)0.25610 (16)0.0458 (7)
O110.90470 (19)0.55429 (16)0.33839 (17)0.0594 (8)
H300.88540.53530.38510.089*
O121.0212 (2)0.6476 (2)0.4053 (2)0.0905 (11)
O130.69748 (17)0.36199 (16)0.47107 (15)0.0442 (6)
O140.81529 (16)0.33779 (16)0.35017 (15)0.0419 (6)
O150.81746 (19)0.47098 (17)0.45115 (16)0.0535 (7)
O160.8698 (2)0.30309 (18)0.49275 (18)0.0668 (9)
H4O0.86420.31220.54410.100*
C10.2734 (2)0.6182 (2)0.2365 (2)0.0357 (8)
C20.2703 (3)0.5561 (3)0.3067 (2)0.0477 (10)
H20.21510.52970.32150.057*
C30.3490 (3)0.5352 (3)0.3527 (2)0.0501 (11)
H30.34730.49460.39980.060*
C40.4334 (3)0.5738 (2)0.3308 (2)0.0431 (9)
C50.5177 (3)0.5497 (3)0.3757 (2)0.0558 (11)
H50.51700.50750.42180.067*
C60.5992 (3)0.5859 (3)0.3540 (3)0.0594 (12)
H60.65340.56910.38500.071*
C70.6010 (3)0.6487 (3)0.2846 (3)0.0564 (11)
H70.65690.67390.26930.068*
C80.5217 (3)0.6737 (2)0.2388 (2)0.0433 (9)
H80.52470.71520.19250.052*
C90.4355 (2)0.6380 (2)0.2602 (2)0.0339 (8)
C100.3506 (2)0.6617 (2)0.2128 (2)0.0327 (8)
C110.3453 (2)0.7269 (2)0.1368 (2)0.0319 (8)
C120.3617 (2)0.8221 (2)0.1423 (2)0.0333 (8)
C130.3790 (2)0.8617 (2)0.2200 (2)0.0408 (9)
H130.38370.82500.26990.049*
C140.3892 (3)0.9527 (3)0.2233 (3)0.0516 (11)
H140.40050.97740.27550.062*
C150.3829 (3)1.0098 (3)0.1496 (3)0.0590 (12)
H150.39091.07180.15260.071*
C160.3652 (3)0.9746 (3)0.0740 (3)0.0546 (11)
H160.36041.01310.02520.066*
C170.3538 (2)0.8803 (2)0.0677 (2)0.0414 (9)
C180.3306 (3)0.8441 (3)−0.0102 (3)0.0518 (11)
H180.32860.8815−0.05980.062*
C190.3109 (3)0.7557 (3)−0.0140 (2)0.0476 (10)
H190.29400.7328−0.06530.057*
C200.3166 (2)0.6998 (2)0.0604 (2)0.0376 (9)
C210.0697 (2)0.2935 (2)0.2883 (2)0.0355 (8)
C220.0694 (3)0.3652 (2)0.3445 (2)0.0471 (10)
H220.02130.41330.34330.056*
C230.1402 (3)0.3640 (2)0.4009 (2)0.0472 (10)
H230.13910.41030.44000.057*
C240.2155 (3)0.2926 (2)0.4005 (2)0.0378 (9)
C250.2931 (3)0.2927 (3)0.4544 (2)0.0496 (10)
H250.29340.33910.49330.059*
C260.3673 (3)0.2266 (3)0.4507 (3)0.0574 (12)
H260.41770.22780.48690.069*
C270.3677 (3)0.1566 (3)0.3926 (3)0.0522 (11)
H270.41940.11220.38920.063*
C280.2937 (2)0.1526 (2)0.3409 (2)0.0412 (9)
H280.29510.10490.30330.049*
C290.2143 (2)0.2193 (2)0.3429 (2)0.0347 (8)
C300.1362 (2)0.2186 (2)0.2876 (2)0.0338 (8)
C310.1291 (2)0.1453 (2)0.2256 (2)0.0343 (8)
C320.1270 (2)0.0499 (2)0.2507 (2)0.0379 (9)
C330.1268 (3)0.0182 (2)0.3370 (3)0.0486 (10)
H330.12860.05990.38010.058*
C340.1239 (3)−0.0734 (3)0.3582 (3)0.0594 (12)
H340.1242−0.09300.41550.071*
C350.1205 (3)−0.1375 (3)0.2948 (3)0.0640 (13)
H350.1198−0.19950.30980.077*
C360.1184 (3)−0.1091 (3)0.2121 (3)0.0577 (12)
H360.1148−0.15180.17020.069*
C370.1214 (3)−0.0157 (2)0.1874 (3)0.0440 (10)
C380.1157 (3)0.0147 (3)0.1011 (3)0.0561 (11)
H380.1127−0.02820.05920.067*
C390.1143 (3)0.1048 (3)0.0774 (3)0.0552 (11)
H390.10940.12410.02020.066*
C400.1203 (2)0.1680 (2)0.1408 (2)0.0397 (9)
C410.8530 (3)0.8082 (2)0.3531 (2)0.0399 (9)
C420.8586 (3)0.8648 (3)0.4221 (2)0.0539 (11)
H420.86180.84030.47790.065*
C430.8590 (3)0.9562 (3)0.4057 (3)0.0548 (11)
H430.86050.99500.45120.066*
C440.8573 (2)0.9938 (2)0.3217 (2)0.0408 (9)
C450.8619 (3)1.0890 (3)0.3046 (3)0.0493 (10)
H450.86401.12780.35010.059*
C460.8633 (3)1.1242 (3)0.2244 (3)0.0510 (11)
H460.86511.18710.21460.061*
C470.8620 (3)1.0669 (3)0.1551 (3)0.0489 (10)
H470.86491.09160.09950.059*
C480.8566 (2)0.9748 (2)0.1687 (2)0.0430 (9)
H480.85540.93760.12200.052*
C490.8529 (2)0.9352 (2)0.2520 (2)0.0353 (8)
C500.8474 (2)0.8389 (2)0.2694 (2)0.0339 (8)
C510.8399 (2)0.7725 (2)0.2006 (2)0.0310 (8)
C520.7632 (2)0.7803 (2)0.1420 (2)0.0351 (8)
C530.6861 (2)0.8493 (2)0.1478 (2)0.0425 (9)
H530.68540.89300.18950.051*
C540.6131 (3)0.8530 (3)0.0937 (3)0.0524 (11)
H540.56270.89840.09950.063*
C550.6125 (3)0.7900 (3)0.0294 (3)0.0603 (12)
H550.56280.7945−0.00820.072*
C560.6846 (3)0.7221 (3)0.0220 (3)0.0565 (11)
H560.68370.6800−0.02080.068*
C570.7612 (3)0.7142 (2)0.0785 (2)0.0394 (9)
C580.8328 (3)0.6398 (3)0.0756 (2)0.0476 (10)
H580.83240.59720.03310.057*
C590.9018 (3)0.6292 (2)0.1337 (2)0.0444 (10)
H590.94740.57880.13250.053*
C600.9032 (2)0.6951 (2)0.1953 (2)0.0371 (9)
C610.6665 (2)0.2751 (2)0.4561 (2)0.0394 (9)
C620.6601 (3)0.2145 (3)0.5262 (2)0.0548 (11)
H620.67110.23260.58100.066*
C630.6376 (3)0.1284 (3)0.5134 (3)0.0579 (12)
H630.63300.08730.55990.070*
C640.6212 (2)0.1006 (3)0.4305 (2)0.0425 (9)
C650.6033 (3)0.0090 (3)0.4153 (3)0.0538 (11)
H650.6003−0.03310.46110.065*
C660.5908 (3)−0.0174 (3)0.3355 (3)0.0564 (11)
H660.5789−0.07740.32650.068*
C670.5955 (3)0.0449 (3)0.2662 (3)0.0498 (10)
H670.58670.02590.21130.060*
C680.6127 (2)0.1327 (2)0.2776 (2)0.0401 (9)
H680.61620.17280.23030.048*
C690.6254 (2)0.1641 (2)0.3600 (2)0.0349 (8)
C700.6473 (2)0.2556 (2)0.3742 (2)0.0342 (8)
C710.6587 (2)0.3251 (2)0.3030 (2)0.0317 (8)
C720.5837 (2)0.3566 (2)0.2458 (2)0.0329 (8)
C730.4919 (2)0.3289 (2)0.2554 (2)0.0428 (9)
H730.47830.28780.29980.051*
C740.4225 (3)0.3615 (3)0.2006 (3)0.0566 (11)
H740.36220.34260.20800.068*
C750.4415 (3)0.4232 (3)0.1334 (3)0.0613 (12)
H750.39400.44480.09590.074*
C760.5286 (3)0.4517 (3)0.1227 (3)0.0582 (12)
H760.54020.49280.07760.070*
C770.6025 (3)0.4205 (2)0.1783 (2)0.0407 (9)
C780.6919 (3)0.4531 (3)0.1695 (2)0.0484 (10)
H780.70400.49400.12440.058*
C790.7611 (3)0.4258 (2)0.2260 (2)0.0461 (10)
H790.81990.44820.22030.055*
C800.7419 (2)0.3634 (2)0.2928 (2)0.0337 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0388 (6)0.0449 (6)0.0489 (6)−0.0139 (5)−0.0092 (5)−0.0012 (5)
P20.0382 (6)0.0351 (6)0.0511 (7)−0.0077 (5)−0.0049 (5)0.0076 (5)
P30.0505 (7)0.0388 (6)0.0553 (7)−0.0066 (5)−0.0177 (5)0.0053 (5)
P40.0491 (7)0.0386 (6)0.0451 (6)−0.0120 (5)−0.0143 (5)−0.0029 (5)
O10.0361 (14)0.0458 (16)0.0484 (16)−0.0107 (12)0.0010 (12)−0.0065 (13)
O20.0435 (15)0.0427 (15)0.0398 (15)−0.0125 (12)−0.0025 (12)−0.0048 (12)
O30.0464 (17)0.084 (2)0.069 (2)−0.0095 (16)−0.0190 (15)0.0150 (17)
O40.0556 (18)0.0504 (17)0.0688 (19)−0.0218 (14)−0.0028 (14)−0.0082 (15)
O50.0351 (14)0.0406 (15)0.0477 (16)−0.0020 (12)−0.0011 (12)0.0017 (12)
O60.0469 (16)0.0410 (15)0.0397 (15)−0.0039 (12)0.0039 (12)0.0036 (12)
O70.0502 (17)0.0348 (15)0.076 (2)−0.0103 (12)−0.0049 (14)0.0083 (14)
O80.0580 (18)0.0645 (19)0.0598 (18)−0.0282 (15)−0.0136 (14)0.0119 (15)
O90.0632 (18)0.0291 (14)0.0445 (15)−0.0081 (13)0.0040 (13)0.0032 (12)
O100.0352 (14)0.0408 (15)0.0611 (18)−0.0031 (12)−0.0039 (13)0.0034 (13)
O110.080 (2)0.0325 (15)0.0662 (19)−0.0093 (14)−0.0035 (16)0.0024 (14)
O120.080 (2)0.105 (3)0.090 (3)−0.016 (2)−0.046 (2)0.009 (2)
O130.0535 (17)0.0446 (16)0.0374 (15)−0.0148 (13)−0.0043 (12)−0.0084 (12)
O140.0359 (14)0.0492 (16)0.0422 (15)−0.0085 (12)−0.0056 (12)−0.0077 (12)
O150.0688 (19)0.0420 (16)0.0540 (17)−0.0209 (14)−0.0117 (14)−0.0085 (13)
O160.081 (2)0.0541 (18)0.067 (2)−0.0076 (16)−0.0331 (17)0.0049 (15)
C10.041 (2)0.035 (2)0.031 (2)−0.0079 (17)0.0027 (17)−0.0035 (16)
C20.060 (3)0.046 (2)0.040 (2)−0.022 (2)0.010 (2)−0.0007 (19)
C30.079 (3)0.040 (2)0.032 (2)−0.013 (2)−0.003 (2)0.0105 (18)
C40.063 (3)0.032 (2)0.036 (2)−0.0077 (19)−0.0034 (19)−0.0024 (17)
C50.075 (3)0.053 (3)0.038 (2)0.004 (2)−0.016 (2)0.001 (2)
C60.064 (3)0.058 (3)0.056 (3)0.006 (2)−0.025 (2)−0.005 (2)
C70.049 (3)0.051 (3)0.071 (3)−0.006 (2)−0.018 (2)−0.002 (2)
C80.045 (2)0.039 (2)0.047 (2)−0.0109 (18)−0.0099 (19)0.0059 (18)
C90.044 (2)0.0285 (19)0.030 (2)−0.0070 (16)−0.0034 (16)−0.0016 (16)
C100.041 (2)0.0271 (19)0.031 (2)−0.0087 (16)0.0002 (16)−0.0019 (15)
C110.0279 (19)0.036 (2)0.032 (2)−0.0075 (15)−0.0043 (15)0.0060 (16)
C120.0274 (19)0.030 (2)0.042 (2)−0.0055 (15)−0.0010 (16)0.0040 (17)
C130.046 (2)0.034 (2)0.043 (2)−0.0069 (18)−0.0033 (18)−0.0003 (18)
C140.052 (3)0.037 (2)0.067 (3)−0.0048 (19)−0.006 (2)−0.010 (2)
C150.061 (3)0.027 (2)0.089 (4)−0.007 (2)−0.004 (3)0.004 (2)
C160.051 (3)0.042 (3)0.069 (3)−0.005 (2)−0.003 (2)0.020 (2)
C170.037 (2)0.038 (2)0.048 (2)−0.0051 (17)−0.0030 (18)0.0096 (19)
C180.051 (3)0.057 (3)0.046 (3)−0.007 (2)−0.008 (2)0.020 (2)
C190.051 (3)0.059 (3)0.035 (2)−0.012 (2)−0.0053 (18)0.006 (2)
C200.034 (2)0.038 (2)0.041 (2)−0.0059 (17)−0.0014 (17)0.0030 (18)
C210.037 (2)0.031 (2)0.039 (2)−0.0070 (17)0.0047 (17)−0.0022 (17)
C220.053 (3)0.030 (2)0.056 (3)0.0039 (19)0.008 (2)−0.0044 (19)
C230.062 (3)0.036 (2)0.045 (2)−0.008 (2)0.008 (2)−0.0097 (18)
C240.046 (2)0.033 (2)0.036 (2)−0.0143 (18)0.0021 (18)−0.0007 (17)
C250.058 (3)0.049 (3)0.046 (2)−0.023 (2)0.000 (2)−0.005 (2)
C260.057 (3)0.071 (3)0.049 (3)−0.025 (3)−0.013 (2)0.007 (2)
C270.042 (2)0.050 (3)0.063 (3)−0.006 (2)−0.005 (2)0.009 (2)
C280.039 (2)0.037 (2)0.047 (2)−0.0013 (18)0.0019 (18)−0.0049 (18)
C290.040 (2)0.030 (2)0.035 (2)−0.0111 (16)0.0025 (17)0.0025 (16)
C300.039 (2)0.0295 (19)0.033 (2)−0.0064 (16)0.0014 (16)0.0007 (16)
C310.031 (2)0.034 (2)0.038 (2)−0.0039 (16)0.0009 (16)−0.0077 (17)
C320.033 (2)0.032 (2)0.049 (2)−0.0020 (16)−0.0029 (17)−0.0050 (18)
C330.054 (3)0.034 (2)0.059 (3)−0.0066 (19)−0.007 (2)0.000 (2)
C340.066 (3)0.043 (3)0.070 (3)−0.011 (2)−0.008 (2)0.011 (2)
C350.064 (3)0.029 (2)0.101 (4)−0.008 (2)−0.013 (3)−0.001 (3)
C360.053 (3)0.039 (3)0.082 (3)−0.004 (2)−0.016 (2)−0.014 (2)
C370.039 (2)0.035 (2)0.059 (3)−0.0034 (18)−0.0042 (19)−0.011 (2)
C380.062 (3)0.050 (3)0.058 (3)−0.003 (2)−0.004 (2)−0.024 (2)
C390.065 (3)0.056 (3)0.045 (3)−0.003 (2)−0.003 (2)−0.012 (2)
C400.043 (2)0.036 (2)0.040 (2)−0.0024 (17)0.0036 (18)−0.0026 (18)
C410.052 (2)0.030 (2)0.038 (2)−0.0067 (18)−0.0003 (18)0.0004 (17)
C420.082 (3)0.050 (3)0.033 (2)−0.018 (2)−0.005 (2)−0.0039 (19)
C430.082 (3)0.040 (2)0.046 (3)−0.017 (2)−0.001 (2)−0.014 (2)
C440.040 (2)0.034 (2)0.050 (2)−0.0093 (17)0.0007 (18)−0.0066 (18)
C450.051 (3)0.035 (2)0.064 (3)−0.0117 (19)−0.007 (2)−0.008 (2)
C460.044 (2)0.030 (2)0.080 (3)−0.0124 (18)−0.006 (2)0.005 (2)
C470.046 (2)0.044 (2)0.056 (3)−0.0094 (19)0.000 (2)0.013 (2)
C480.043 (2)0.038 (2)0.048 (2)−0.0068 (18)0.0031 (18)0.0031 (19)
C490.035 (2)0.0269 (19)0.044 (2)−0.0022 (16)−0.0012 (17)−0.0017 (17)
C500.033 (2)0.030 (2)0.039 (2)−0.0049 (16)0.0003 (16)−0.0029 (16)
C510.035 (2)0.0256 (18)0.033 (2)−0.0059 (15)0.0042 (16)−0.0011 (15)
C520.038 (2)0.030 (2)0.038 (2)−0.0104 (16)0.0033 (17)0.0008 (16)
C530.039 (2)0.040 (2)0.047 (2)−0.0041 (18)−0.0020 (19)0.0027 (18)
C540.043 (2)0.056 (3)0.058 (3)−0.008 (2)−0.005 (2)0.011 (2)
C550.060 (3)0.075 (3)0.050 (3)−0.025 (3)−0.020 (2)0.014 (2)
C560.074 (3)0.059 (3)0.041 (2)−0.027 (3)−0.010 (2)−0.004 (2)
C570.049 (2)0.034 (2)0.036 (2)−0.0119 (18)0.0054 (18)−0.0032 (17)
C580.067 (3)0.042 (2)0.037 (2)−0.018 (2)0.013 (2)−0.0165 (19)
C590.048 (2)0.032 (2)0.053 (3)−0.0029 (18)0.012 (2)−0.0079 (19)
C600.033 (2)0.038 (2)0.040 (2)−0.0050 (17)0.0038 (17)−0.0003 (17)
C610.043 (2)0.040 (2)0.036 (2)−0.0093 (18)−0.0023 (17)−0.0031 (18)
C620.065 (3)0.070 (3)0.033 (2)−0.022 (2)−0.012 (2)0.004 (2)
C630.067 (3)0.057 (3)0.051 (3)−0.016 (2)−0.006 (2)0.017 (2)
C640.039 (2)0.042 (2)0.047 (2)−0.0062 (18)−0.0060 (18)0.0086 (19)
C650.053 (3)0.039 (2)0.069 (3)−0.006 (2)−0.001 (2)0.015 (2)
C660.057 (3)0.032 (2)0.081 (3)−0.006 (2)−0.002 (2)−0.007 (2)
C670.051 (3)0.041 (2)0.059 (3)−0.008 (2)−0.002 (2)−0.014 (2)
C680.042 (2)0.036 (2)0.042 (2)−0.0073 (18)−0.0020 (18)−0.0031 (18)
C690.032 (2)0.035 (2)0.038 (2)−0.0061 (16)−0.0011 (16)−0.0022 (17)
C700.034 (2)0.034 (2)0.035 (2)−0.0062 (16)−0.0021 (16)−0.0031 (16)
C710.037 (2)0.0302 (19)0.0291 (19)−0.0092 (16)0.0005 (16)−0.0033 (15)
C720.035 (2)0.0301 (19)0.034 (2)−0.0029 (16)−0.0038 (16)−0.0056 (16)
C730.041 (2)0.042 (2)0.047 (2)−0.0089 (18)−0.0074 (18)−0.0053 (18)
C740.045 (3)0.055 (3)0.071 (3)−0.005 (2)−0.018 (2)−0.009 (2)
C750.068 (3)0.050 (3)0.064 (3)0.011 (2)−0.033 (2)−0.010 (2)
C760.075 (3)0.048 (3)0.052 (3)−0.005 (2)−0.023 (2)0.006 (2)
C770.054 (2)0.033 (2)0.036 (2)−0.0048 (18)−0.0052 (18)−0.0022 (17)
C780.066 (3)0.043 (2)0.038 (2)−0.018 (2)−0.002 (2)0.0035 (19)
C790.047 (2)0.046 (2)0.048 (2)−0.0181 (19)0.004 (2)−0.008 (2)
C800.036 (2)0.033 (2)0.033 (2)−0.0040 (16)−0.0006 (16)−0.0088 (16)

Geometric parameters (Å, °)

P1—O31.457 (3)C32—C371.417 (5)
P1—O41.529 (3)C33—C341.374 (5)
P1—O11.572 (3)C33—H330.9300
P1—O21.583 (2)C34—C351.399 (6)
P2—O71.471 (2)C34—H340.9300
P2—O81.519 (3)C35—C361.344 (6)
P2—O51.576 (2)C35—H350.9300
P2—O61.578 (2)C36—C371.411 (5)
P3—O121.442 (3)C36—H360.9300
P3—O111.528 (3)C37—C381.406 (5)
P3—O101.572 (3)C38—C391.356 (5)
P3—O91.578 (3)C38—H380.9300
P4—O151.466 (2)C39—C401.393 (5)
P4—O161.524 (3)C39—H390.9300
P4—O141.576 (2)C41—C501.369 (5)
P4—O131.578 (3)C41—C421.396 (5)
O1—C11.416 (4)C42—C431.354 (5)
O2—C201.416 (4)C42—H420.9300
O4—H1O0.8200C43—C441.405 (5)
O5—C211.408 (4)C43—H430.9300
O6—C401.413 (4)C44—C451.418 (5)
O8—H2O0.8200C44—C491.421 (5)
O9—C411.412 (4)C45—C461.338 (5)
O10—C601.413 (4)C45—H450.9300
O11—H300.8200C46—C471.398 (5)
O13—C611.420 (4)C46—H460.9300
O14—C801.410 (4)C47—C481.368 (5)
O16—H4O0.8200C47—H470.9300
C1—C101.360 (4)C48—C491.405 (5)
C1—C21.400 (5)C48—H480.9300
C2—C31.352 (5)C49—C501.436 (4)
C2—H20.9300C50—C511.493 (4)
C3—C41.405 (5)C51—C601.373 (4)
C3—H30.9300C51—C521.441 (4)
C4—C51.415 (5)C52—C531.414 (5)
C4—C91.424 (5)C52—C571.418 (5)
C5—C61.351 (6)C53—C541.356 (5)
C5—H50.9300C53—H530.9300
C6—C71.398 (5)C54—C551.391 (5)
C6—H60.9300C54—H540.9300
C7—C81.365 (5)C55—C561.356 (5)
C7—H70.9300C55—H550.9300
C8—C91.407 (5)C56—C571.417 (5)
C8—H80.9300C56—H560.9300
C9—C101.441 (4)C57—C581.412 (5)
C10—C111.493 (4)C58—C591.351 (5)
C11—C201.363 (4)C58—H580.9300
C11—C121.444 (4)C59—C601.394 (5)
C12—C131.407 (5)C59—H590.9300
C12—C171.419 (4)C61—C701.367 (4)
C13—C141.359 (5)C61—C621.390 (5)
C13—H130.9300C62—C631.357 (5)
C14—C151.397 (5)C62—H620.9300
C14—H140.9300C63—C641.409 (5)
C15—C161.350 (5)C63—H630.9300
C15—H150.9300C64—C691.417 (5)
C16—C171.416 (5)C64—C651.421 (5)
C16—H160.9300C65—C661.345 (5)
C17—C181.410 (5)C65—H650.9300
C18—C191.358 (5)C66—C671.393 (5)
C18—H180.9300C66—H660.9300
C19—C201.396 (5)C67—C681.353 (5)
C19—H190.9300C67—H670.9300
C21—C301.372 (4)C68—C691.410 (5)
C21—C221.395 (5)C68—H680.9300
C22—C231.358 (5)C69—C701.436 (4)
C22—H220.9300C70—C711.494 (4)
C23—C241.416 (5)C71—C801.364 (4)
C23—H230.9300C71—C721.441 (4)
C24—C251.411 (5)C72—C731.408 (5)
C24—C291.431 (5)C72—C771.420 (5)
C25—C261.356 (5)C73—C741.364 (5)
C25—H250.9300C73—H730.9300
C26—C271.397 (5)C74—C751.396 (6)
C26—H260.9300C74—H740.9300
C27—C281.356 (5)C75—C761.351 (6)
C27—H270.9300C75—H750.9300
C28—C291.412 (5)C76—C771.413 (5)
C28—H280.9300C76—H760.9300
C29—C301.431 (5)C77—C781.404 (5)
C30—C311.488 (4)C78—C791.362 (5)
C31—C401.361 (5)C78—H780.9300
C31—C321.440 (5)C79—C801.399 (5)
C32—C331.409 (5)C79—H790.9300
O3—P1—O4117.18 (16)C36—C35—C34119.7 (4)
O3—P1—O1107.23 (16)C36—C35—H35120.2
O4—P1—O1110.50 (14)C34—C35—H35120.2
O3—P1—O2115.41 (15)C35—C36—C37121.4 (4)
O4—P1—O2100.66 (14)C35—C36—H36119.3
O1—P1—O2105.23 (13)C37—C36—H36119.3
O7—P2—O8116.74 (15)C38—C37—C36121.4 (4)
O7—P2—O5114.68 (15)C38—C37—C32118.8 (3)
O8—P2—O5100.86 (14)C36—C37—C32119.7 (4)
O7—P2—O6108.12 (14)C39—C38—C37121.6 (4)
O8—P2—O6111.19 (15)C39—C38—H38119.2
O5—P2—O6104.54 (13)C37—C38—H38119.2
O12—P3—O11116.93 (18)C38—C39—C40118.5 (4)
O12—P3—O10109.23 (18)C38—C39—H39120.8
O11—P3—O10106.08 (15)C40—C39—H39120.8
O12—P3—O9114.84 (19)C31—C40—C39124.4 (4)
O11—P3—O9103.64 (14)C31—C40—O6119.2 (3)
O10—P3—O9105.14 (13)C39—C40—O6116.4 (3)
O15—P4—O16117.59 (16)C50—C41—C42124.4 (3)
O15—P4—O14114.69 (15)C50—C41—O9118.9 (3)
O16—P4—O14101.59 (15)C42—C41—O9116.7 (3)
O15—P4—O13107.79 (15)C43—C42—C41118.2 (4)
O16—P4—O13109.82 (15)C43—C42—H42120.9
O14—P4—O13104.53 (13)C41—C42—H42120.9
C1—O1—P1117.7 (2)C42—C43—C44121.6 (4)
C20—O2—P1114.8 (2)C42—C43—H43119.2
P1—O4—H1O109.5C44—C43—H43119.2
C21—O5—P2116.8 (2)C43—C44—C45121.3 (4)
C40—O6—P2118.2 (2)C43—C44—C49119.6 (3)
P2—O8—H2O109.5C45—C44—C49119.1 (3)
C41—O9—P3118.8 (2)C46—C45—C44121.2 (4)
C60—O10—P3116.4 (2)C46—C45—H45119.4
P3—O11—H30109.5C44—C45—H45119.4
C61—O13—P4116.0 (2)C45—C46—C47120.3 (4)
C80—O14—P4118.2 (2)C45—C46—H46119.9
P4—O16—H4O109.5C47—C46—H46119.9
C10—C1—C2123.8 (3)C48—C47—C46120.4 (4)
C10—C1—O1119.1 (3)C48—C47—H47119.8
C2—C1—O1117.1 (3)C46—C47—H47119.8
C3—C2—C1118.9 (4)C47—C48—C49121.2 (4)
C3—C2—H2120.6C47—C48—H48119.4
C1—C2—H2120.6C49—C48—H48119.4
C2—C3—C4121.3 (3)C48—C49—C44117.8 (3)
C2—C3—H3119.3C48—C49—C50123.2 (3)
C4—C3—H3119.3C44—C49—C50119.0 (3)
C3—C4—C5122.2 (4)C41—C50—C49117.1 (3)
C3—C4—C9119.4 (3)C41—C50—C51119.9 (3)
C5—C4—C9118.4 (4)C49—C50—C51122.9 (3)
C6—C5—C4122.2 (4)C60—C51—C52116.3 (3)
C6—C5—H5118.9C60—C51—C50120.4 (3)
C4—C5—H5118.9C52—C51—C50123.1 (3)
C5—C6—C7119.3 (4)C53—C52—C57117.9 (3)
C5—C6—H6120.4C53—C52—C51122.4 (3)
C7—C6—H6120.4C57—C52—C51119.7 (3)
C8—C7—C6120.7 (4)C54—C53—C52121.1 (4)
C8—C7—H7119.7C54—C53—H53119.4
C6—C7—H7119.7C52—C53—H53119.4
C7—C8—C9121.5 (4)C53—C54—C55121.1 (4)
C7—C8—H8119.2C53—C54—H54119.4
C9—C8—H8119.2C55—C54—H54119.4
C8—C9—C4117.9 (3)C56—C55—C54119.7 (4)
C8—C9—C10123.2 (3)C56—C55—H55120.1
C4—C9—C10118.9 (3)C54—C55—H55120.1
C1—C10—C9117.6 (3)C55—C56—C57121.1 (4)
C1—C10—C11119.0 (3)C55—C56—H56119.4
C9—C10—C11123.4 (3)C57—C56—H56119.4
C20—C11—C12117.2 (3)C58—C57—C56121.6 (4)
C20—C11—C10120.2 (3)C58—C57—C52119.3 (3)
C12—C11—C10122.3 (3)C56—C57—C52119.0 (4)
C13—C12—C17117.9 (3)C59—C58—C57121.2 (3)
C13—C12—C11122.9 (3)C59—C58—H58119.4
C17—C12—C11119.1 (3)C57—C58—H58119.4
C14—C13—C12121.2 (3)C58—C59—C60118.7 (4)
C14—C13—H13119.4C58—C59—H59120.6
C12—C13—H13119.4C60—C59—H59120.6
C13—C14—C15120.9 (4)C51—C60—C59124.5 (3)
C13—C14—H14119.6C51—C60—O10118.9 (3)
C15—C14—H14119.6C59—C60—O10116.6 (3)
C16—C15—C14119.8 (4)C70—C61—C62124.3 (3)
C16—C15—H15120.1C70—C61—O13118.3 (3)
C14—C15—H15120.1C62—C61—O13117.3 (3)
C15—C16—C17121.2 (4)C63—C62—C61118.9 (4)
C15—C16—H16119.4C63—C62—H62120.5
C17—C16—H16119.4C61—C62—H62120.5
C18—C17—C16121.4 (4)C62—C63—C64120.7 (4)
C18—C17—C12119.5 (3)C62—C63—H63119.6
C16—C17—C12119.0 (4)C64—C63—H63119.6
C19—C18—C17121.0 (4)C63—C64—C69119.6 (3)
C19—C18—H18119.5C63—C64—C65121.4 (4)
C17—C18—H18119.5C69—C64—C65119.0 (4)
C18—C19—C20118.8 (4)C66—C65—C64120.8 (4)
C18—C19—H19120.6C66—C65—H65119.6
C20—C19—H19120.6C64—C65—H65119.6
C11—C20—C19124.0 (3)C65—C66—C67120.2 (4)
C11—C20—O2118.7 (3)C65—C66—H66119.9
C19—C20—O2117.2 (3)C67—C66—H66119.9
C30—C21—C22124.0 (3)C68—C67—C66121.1 (4)
C30—C21—O5119.4 (3)C68—C67—H67119.5
C22—C21—O5116.6 (3)C66—C67—H67119.5
C23—C22—C21119.5 (4)C67—C68—C69121.0 (4)
C23—C22—H22120.3C67—C68—H68119.5
C21—C22—H22120.3C69—C68—H68119.5
C22—C23—C24120.3 (4)C68—C69—C64118.0 (3)
C22—C23—H23119.8C68—C69—C70122.5 (3)
C24—C23—H23119.8C64—C69—C70119.4 (3)
C25—C24—C23121.6 (4)C61—C70—C69116.9 (3)
C25—C24—C29118.9 (3)C61—C70—C71120.0 (3)
C23—C24—C29119.5 (3)C69—C70—C71122.8 (3)
C26—C25—C24121.4 (4)C80—C71—C72117.8 (3)
C26—C25—H25119.3C80—C71—C70119.4 (3)
C24—C25—H25119.3C72—C71—C70122.8 (3)
C25—C26—C27119.9 (4)C73—C72—C77118.6 (3)
C25—C26—H26120.1C73—C72—C71122.9 (3)
C27—C26—H26120.1C77—C72—C71118.5 (3)
C28—C27—C26120.7 (4)C74—C73—C72121.1 (4)
C28—C27—H27119.6C74—C73—H73119.5
C26—C27—H27119.6C72—C73—H73119.5
C27—C28—C29121.6 (4)C73—C74—C75120.3 (4)
C27—C28—H28119.2C73—C74—H74119.8
C29—C28—H28119.2C75—C74—H74119.8
C28—C29—C24117.5 (3)C76—C75—C74120.2 (4)
C28—C29—C30123.0 (3)C76—C75—H75119.9
C24—C29—C30119.4 (3)C74—C75—H75119.9
C21—C30—C29117.1 (3)C75—C76—C77121.6 (4)
C21—C30—C31119.6 (3)C75—C76—H76119.2
C29—C30—C31123.1 (3)C77—C76—H76119.2
C40—C31—C32116.8 (3)C78—C77—C76121.6 (4)
C40—C31—C30119.8 (3)C78—C77—C72120.1 (3)
C32—C31—C30123.3 (3)C76—C77—C72118.3 (4)
C33—C32—C37117.5 (3)C79—C78—C77121.0 (3)
C33—C32—C31122.7 (3)C79—C78—H78119.5
C37—C32—C31119.7 (3)C77—C78—H78119.5
C34—C33—C32120.9 (4)C78—C79—C80118.6 (3)
C34—C33—H33119.6C78—C79—H79120.7
C32—C33—H33119.6C80—C79—H79120.7
C33—C34—C35120.8 (4)C71—C80—C79123.8 (3)
C33—C34—H34119.6C71—C80—O14119.5 (3)
C35—C34—H34119.6C79—C80—O14116.7 (3)
O3—P1—O1—C1−165.3 (2)C31—C32—C37—C36−179.3 (3)
O4—P1—O1—C165.9 (3)C36—C37—C38—C39177.0 (4)
O2—P1—O1—C1−41.9 (3)C32—C37—C38—C39−0.7 (6)
O3—P1—O2—C2068.8 (3)C37—C38—C39—C401.1 (6)
O4—P1—O2—C20−164.0 (2)C32—C31—C40—C39−3.3 (5)
O1—P1—O2—C20−49.1 (2)C30—C31—C40—C39179.2 (3)
O7—P2—O5—C21−71.7 (3)C32—C31—C40—O6176.4 (3)
O8—P2—O5—C21161.9 (2)C30—C31—C40—O6−1.1 (5)
O6—P2—O5—C2146.5 (3)C38—C39—C40—C311.1 (6)
O7—P2—O6—C40166.8 (2)C38—C39—C40—O6−178.7 (3)
O8—P2—O6—C40−63.8 (3)P2—O6—C40—C31−73.1 (4)
O5—P2—O6—C4044.2 (3)P2—O6—C40—C39106.7 (3)
O12—P3—O9—C4176.8 (3)P3—O9—C41—C5072.1 (4)
O11—P3—O9—C41−154.4 (2)P3—O9—C41—C42−108.2 (3)
O10—P3—O9—C41−43.3 (3)C50—C41—C42—C43−0.4 (6)
O12—P3—O10—C60−171.3 (3)O9—C41—C42—C43180.0 (3)
O11—P3—O10—C6061.8 (3)C41—C42—C43—C44−2.2 (6)
O9—P3—O10—C60−47.6 (3)C42—C43—C44—C45−177.3 (4)
O15—P4—O13—C61171.0 (2)C42—C43—C44—C491.4 (6)
O16—P4—O13—C61−59.8 (3)C43—C44—C45—C46177.9 (4)
O14—P4—O13—C6148.5 (3)C49—C44—C45—C46−0.9 (6)
O15—P4—O14—C80−75.0 (3)C44—C45—C46—C47−1.2 (6)
O16—P4—O14—C80157.0 (2)C45—C46—C47—C481.9 (6)
O13—P4—O14—C8042.8 (3)C46—C47—C48—C49−0.4 (6)
P1—O1—C1—C1073.7 (4)C47—C48—C49—C44−1.6 (5)
P1—O1—C1—C2−107.5 (3)C47—C48—C49—C50−179.8 (3)
C10—C1—C2—C3−2.1 (6)C43—C44—C49—C48−176.5 (3)
O1—C1—C2—C3179.2 (3)C45—C44—C49—C482.2 (5)
C1—C2—C3—C4−0.7 (6)C43—C44—C49—C501.8 (5)
C2—C3—C4—C5−177.1 (4)C45—C44—C49—C50−179.5 (3)
C2—C3—C4—C91.7 (6)C42—C41—C50—C493.5 (6)
C3—C4—C5—C6179.1 (4)O9—C41—C50—C49−176.9 (3)
C9—C4—C5—C60.3 (6)C42—C41—C50—C51−178.8 (3)
C4—C5—C6—C7−0.5 (6)O9—C41—C50—C510.8 (5)
C5—C6—C7—C80.0 (6)C48—C49—C50—C41174.1 (3)
C6—C7—C8—C90.6 (6)C44—C49—C50—C41−4.1 (5)
C7—C8—C9—C4−0.7 (5)C48—C49—C50—C51−3.4 (5)
C7—C8—C9—C10−179.1 (3)C44—C49—C50—C51178.3 (3)
C3—C4—C9—C8−178.6 (3)C41—C50—C51—C60−51.4 (5)
C5—C4—C9—C80.2 (5)C49—C50—C51—C60126.1 (4)
C3—C4—C9—C10−0.1 (5)C41—C50—C51—C52122.8 (4)
C5—C4—C9—C10178.7 (3)C49—C50—C51—C52−59.7 (5)
C2—C1—C10—C93.6 (5)C60—C51—C52—C53171.2 (3)
O1—C1—C10—C9−177.7 (3)C50—C51—C52—C53−3.2 (5)
C2—C1—C10—C11−179.7 (3)C60—C51—C52—C57−5.5 (5)
O1—C1—C10—C11−1.0 (5)C50—C51—C52—C57−179.9 (3)
C8—C9—C10—C1176.0 (3)C57—C52—C53—C54−0.8 (5)
C4—C9—C10—C1−2.4 (5)C51—C52—C53—C54−177.6 (3)
C8—C9—C10—C11−0.6 (5)C52—C53—C54—C55−1.3 (6)
C4—C9—C10—C11−178.9 (3)C53—C54—C55—C561.8 (6)
C1—C10—C11—C20−52.8 (5)C54—C55—C56—C57−0.3 (6)
C9—C10—C11—C20123.7 (4)C55—C56—C57—C58175.0 (4)
C1—C10—C11—C12121.6 (4)C55—C56—C57—C52−1.8 (6)
C9—C10—C11—C12−61.9 (5)C53—C52—C57—C58−174.5 (3)
C20—C11—C12—C13171.2 (3)C51—C52—C57—C582.3 (5)
C10—C11—C12—C13−3.3 (5)C53—C52—C57—C562.3 (5)
C20—C11—C12—C17−4.4 (5)C51—C52—C57—C56179.2 (3)
C10—C11—C12—C17−179.0 (3)C56—C57—C58—C59−175.1 (3)
C17—C12—C13—C14−0.8 (5)C52—C57—C58—C591.6 (5)
C11—C12—C13—C14−176.5 (3)C57—C58—C59—C60−2.1 (5)
C12—C13—C14—C15−0.2 (6)C52—C51—C60—C595.3 (5)
C13—C14—C15—C160.9 (6)C50—C51—C60—C59179.9 (3)
C14—C15—C16—C17−0.7 (6)C52—C51—C60—O10−174.4 (3)
C15—C16—C17—C18176.7 (4)C50—C51—C60—O100.1 (5)
C15—C16—C17—C12−0.3 (6)C58—C59—C60—C51−1.5 (5)
C13—C12—C17—C18−176.1 (3)C58—C59—C60—O10178.2 (3)
C11—C12—C17—C18−0.2 (5)P3—O10—C60—C5174.6 (3)
C13—C12—C17—C161.0 (5)P3—O10—C60—C59−105.1 (3)
C11—C12—C17—C16176.9 (3)P4—O13—C61—C70−75.9 (4)
C16—C17—C18—C19−173.7 (4)P4—O13—C61—C62102.5 (3)
C12—C17—C18—C193.3 (6)C70—C61—C62—C633.2 (6)
C17—C18—C19—C20−1.7 (6)O13—C61—C62—C63−175.1 (3)
C12—C11—C20—C196.4 (5)C61—C62—C63—C640.2 (6)
C10—C11—C20—C19−179.0 (3)C62—C63—C64—C69−1.9 (6)
C12—C11—C20—O2−172.6 (3)C62—C63—C64—C65176.1 (4)
C10—C11—C20—O22.0 (5)C63—C64—C65—C66−177.9 (4)
C18—C19—C20—C11−3.4 (6)C69—C64—C65—C660.1 (6)
C18—C19—C20—O2175.6 (3)C64—C65—C66—C670.3 (6)
P1—O2—C20—C1174.7 (3)C65—C66—C67—C680.0 (6)
P1—O2—C20—C19−104.3 (3)C66—C67—C68—C69−0.7 (6)
P2—O5—C21—C30−74.2 (3)C67—C68—C69—C641.0 (5)
P2—O5—C21—C22105.9 (3)C67—C68—C69—C70177.6 (3)
C30—C21—C22—C232.2 (6)C63—C64—C69—C68177.3 (3)
O5—C21—C22—C23−177.9 (3)C65—C64—C69—C68−0.8 (5)
C21—C22—C23—C242.4 (6)C63—C64—C69—C700.6 (5)
C22—C23—C24—C25175.7 (3)C65—C64—C69—C70−177.4 (3)
C22—C23—C24—C29−2.9 (5)C62—C61—C70—C69−4.4 (5)
C23—C24—C25—C26−176.6 (4)O13—C61—C70—C69173.9 (3)
C29—C24—C25—C262.0 (5)C62—C61—C70—C71−178.5 (3)
C24—C25—C26—C270.1 (6)O13—C61—C70—C71−0.2 (5)
C25—C26—C27—C28−1.6 (6)C68—C69—C70—C61−174.1 (3)
C26—C27—C28—C290.9 (6)C64—C69—C70—C612.4 (5)
C27—C28—C29—C241.1 (5)C68—C69—C70—C71−0.1 (5)
C27—C28—C29—C30178.1 (3)C64—C69—C70—C71176.4 (3)
C25—C24—C29—C28−2.5 (5)C61—C70—C71—C8052.1 (5)
C23—C24—C29—C28176.1 (3)C69—C70—C71—C80−121.7 (4)
C25—C24—C29—C30−179.7 (3)C61—C70—C71—C72−125.5 (4)
C23—C24—C29—C30−1.0 (5)C69—C70—C71—C7260.7 (5)
C22—C21—C30—C29−5.9 (5)C80—C71—C72—C73−173.5 (3)
O5—C21—C30—C29174.1 (3)C70—C71—C72—C734.0 (5)
C22—C21—C30—C31179.1 (3)C80—C71—C72—C774.5 (5)
O5—C21—C30—C31−0.8 (5)C70—C71—C72—C77−177.9 (3)
C28—C29—C30—C21−171.8 (3)C77—C72—C73—C740.9 (5)
C24—C29—C30—C215.2 (5)C71—C72—C73—C74178.9 (3)
C28—C29—C30—C313.0 (5)C72—C73—C74—C750.1 (6)
C24—C29—C30—C31179.9 (3)C73—C74—C75—C76−0.6 (6)
C21—C30—C31—C4052.2 (5)C74—C75—C76—C770.0 (6)
C29—C30—C31—C40−122.4 (4)C75—C76—C77—C78−177.1 (4)
C21—C30—C31—C32−125.1 (4)C75—C76—C77—C721.0 (6)
C29—C30—C31—C3260.3 (5)C73—C72—C77—C78176.8 (3)
C40—C31—C32—C33−174.1 (3)C71—C72—C77—C78−1.4 (5)
C30—C31—C32—C333.3 (5)C73—C72—C77—C76−1.4 (5)
C40—C31—C32—C373.5 (5)C71—C72—C77—C76−179.6 (3)
C30—C31—C32—C37−179.1 (3)C76—C77—C78—C79176.8 (4)
C37—C32—C33—C341.8 (5)C72—C77—C78—C79−1.3 (6)
C31—C32—C33—C34179.4 (3)C77—C78—C79—C800.8 (6)
C32—C33—C34—C35−0.4 (6)C72—C71—C80—C79−5.3 (5)
C33—C34—C35—C36−1.2 (7)C70—C71—C80—C79177.0 (3)
C34—C35—C36—C371.3 (6)C72—C71—C80—O14176.8 (3)
C35—C36—C37—C38−177.6 (4)C70—C71—C80—O14−0.8 (5)
C35—C36—C37—C320.1 (6)C78—C79—C80—C712.7 (5)
C33—C32—C37—C38176.2 (3)C78—C79—C80—O14−179.4 (3)
C31—C32—C37—C38−1.6 (5)P4—O14—C80—C71−72.6 (4)
C33—C32—C37—C36−1.6 (5)P4—O14—C80—C79109.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H1O···O70.821.782.475 (4)141
O8—H2O···O3i0.821.772.450 (4)139
O16—H4O···O12ii0.821.992.441 (4)114
O11—H30···O150.821.712.477 (4)154
C22—H22···O11iii0.932.513.435 (4)174
C59—H59···O7iv0.932.563.478 (4)167
C27—H27···Cg10.932.753.567 (5)147
C54—H54···Cg2v0.932.773.535 (5)140

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LN2013).

References

  • An, J., Wilson, J. M., An, Y. Z. & Wiemer, D. W. (1996). J. Org. Chem.61, 4040–4045. [PubMed]
  • Arnold, W., Daly, J. J., Imhof, R. & Kyburz, E. (1983). Tetrahedron Lett.24, 343–346.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2004). SMART (Version 5.628) and SAINT (Version 6.45a). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Etter, M. C. & Baures, P. W. (1988). J. Am. Chem. Soc.110, 639–640.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Fujii, I. & Hirayamma, N. (2002). Helv. Chim. Acta, 85, 2946–2960.
  • Jacques, J., Collet, A. & Wilen, S. H. (1981). Enantiomers, Racemates and Resolutions, chs. 1–4. New York: John Wiley & Sons.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON Chemical Crystallography Laboratory, University of Oxford, England.
  • Wilen, S. H., Qi, J. Z. & Williard, P. G. (1991). J. Org. Chem.56, 485–487.

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