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ISSN: 2056-9890
Volume 69| Part 8| August 2013| Pages o1362-o1363

Tris(4-formyl­phen­yl)phosphane oxide tetra­hydro­furan hemisolvate

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu

(Received 25 June 2013; accepted 19 July 2013; online 31 July 2013)

The title compound, C21H15O4P·0.5C4H8O, contains an ordered phosphane oxide in a general position and a tetra­hydro­furan solvent mol­ecule disordered about a twofold axis. All three aldehyde substituents are nearly coplanar with their attached benzene rings, with C—C—C—O torsion angles in the range 1.64 (17)–4.24 (19)°. All three have different conformations with respect to the P=O group, one syn, one anti, and one gauche. Two of the aldehyde substituents form inter­molecular C—H⋯O contacts.

Related literature

For synthetic procedures, see: Bartlett et al. (1978[Bartlett, P. A., Bauer, B. & Singer, S. J. (1978). J. Am. Chem. Soc. 100, 5085-5089.]); Chalier et al. (1996[Chalier, F., Berchadsky, Y., Finet, J. P., Gronchi, G., Marque, S. & Tordo, P. (1996). J. Phys. Chem. 100, 4323-4330.]); Kumagai & Itsuno (2001[Kumagai, T. & Itsuno, S. (2001). Tetrahedron Asymmetry, 12, 2509-2516.]). For use as a precursor in supra­molecular chemistry, see: Kakoullis (2007[Kakoullis, J. (2007). MS thesis, Louisiana State University, Baton Rouge, USA.]); Pariya et al. (2008[Pariya, C., Marcos, Y. S., Zhang, Y., Fronczek, F. R. & Maverick, A. W. (2008). Organometallics, 27, 4318-4324.]). For weak hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]). For related structures, see: Daly (1964[Daly, J. J. (1964). J. Chem. Soc. pp. 3799-3810.]); Etter & Baures (1988[Etter, M. C. & Baures, P. W. (1988). J. Am. Chem. Soc. 110, 639-640.]); Siegler et al. (2007[Siegler, M. A., Fu, Y., Simpson, G. H., King, D. P., Parkin, S. & Brock, C. P. (2007). Acta Cryst. B63, 912-925.]); Spek (1987[Spek, A. L. (1987). Acta Cryst. C43, 1233-1235.]); Brock et al. (1985[Brock, C. P., Schweizer, W. B. & Dunitz, J. D. (1985). J. Am. Chem. Soc. 107, 6964-6970.]); Lenstra (2007[Lenstra, A. T. (2007). Private communication (refcode TPEPGO12). CCDC, Cambridge, England.]); Thierbach et al. (1980[Thierbach, D., Huber, F. & Preut, H. (1980). Acta Cryst. B36, 974-977.]); Baures & Silverton (1990[Baures, P. W. & Silverton, J. V. (1990). Acta Cryst. C46, 715-717.]); Baures (1991[Baures, P. W. (1991). Acta Cryst. C47, 2715-2716.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15O4P·0.5C4H8O

  • Mr = 398.35

  • Monoclinic, C 2/c

  • a = 21.371 (3) Å

  • b = 13.474 (2) Å

  • c = 13.436 (2) Å

  • β = 99.018 (9)°

  • V = 3821.1 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 110 K

  • 0.45 × 0.43 × 0.38 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.926, Tmax = 0.937

  • 36155 measured reflections

  • 7598 independent reflections

  • 5928 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.03

  • 7598 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7⋯O3i 0.95 2.56 3.4303 (16) 152
C14—H14⋯O1ii 0.95 2.50 3.1575 (14) 127
Symmetry codes: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Triphenylphosphane oxide (TPPO) has been extensively structurally studied, as a result of the high basicity of its O atom, which makes it an excellent hydrogen-bond acceptor. Its utility as a crystallization aid for molecules having hydrogen-bond donors was reported by Etter & Baures (1988), which has led to its use in forming molecular cocrystals (Siegler et al., 2007). Also, it has four known polymorphs (Spek, 1987; Brock et al., 1985; Lenstra, 2007) and several known solvates (Thierbach et al., 1980; Baures & Silverton, 1990; Baures, 1991).

Tris(4-formylphenyl)phosphane was first reported by Bartlett et al. (1978), but was also synthesized later by other groups (Chalier et al., 1996). Our interest in the phosphane and the corresponding phosphane oxide (I) stems from their use as precursors to multifunctional ligands for supramolecular chemistry (Kakoullis, 2007; Pariya et al., 2008;). The structure of (I) is illustrated in Fig. 1, showing only one orientation of the THF solvent molecule, which is disordered about a twofold axis. Atom C2S lies 0.51 Å from that axis, and the nearest distance between partially populated sites is 1.00 Å (C2S···C3S at 1 - x, y, 3/2 - z), so the resolution of the data (0.64 Å) allowed individual refinement of the partially populated positions without constraint. The three aldehyde substituents are nearly coplanar with the phenyl groups to which they are attached, with maximum torsion angle magnitude 4.24 (19) ° for C17—C18—C21—O4. The three 4-formylphenyl groups all have different conformations with respect to the phosphane oxide bond. Aldehyde C7O2 is syn to P1O1, with O1—P1···C7—O2 torsion angle -11.6 (1)°, while the corresponding torsion angles are 78.8 (1)° for O3 and -172.6 (1)° for O4. Intermolecular interactions include C—H···O contacts (Desiraju & Steiner, 1999) for two of the three aldehydes as donors. These are C7—H···O3(1/2 + x, 1/2 + y, z) with C···O distance 3.4303 (16) Å and 152° angle about H, and the shorter but less linear contact C14—H···O1(1/2 - x, 1/2 - y, 1 - z), 3.1575 (14) Å and 127°.

Related literature top

For synthetic procedures, see: Bartlett et al. (1978); Chalier et al. (1996); Kumagai & Itsuno (2001). For use as a precursor in supramolecular chemistry, see: Kakoullis (2007); Pariya et al. (2008). For weak hydrogen bonds, see: Desiraju & Steiner (1999). For related structures, see: Daly (1964); Etter & Baures (1988); Siegler et al. (2007); Spek (1987); Brock et al. (1985); Lenstra (2007); Thierbach et al. (1980); Baures & Silverton (1990); Baures (1991).

Experimental top

To prepare (I), the precursor tris(4-formylphenyl)phosphane was first prepared following and combining elements of the procedures for the synthesis of tris(4-formylphenyl)phosphane (Bartlett et al., 1978) and bis(4-formylphenyl)dimethylsilane (Kumagai & Itsuno, 2001). A sample of 4-bromobenzaldehyde dimethyl acetal (5 ml, 29.9 mmol) was combined with 40 ml dry THF in an inert atmosphere in a round-bottom flask. The solution was brought to -78 °C under streaming N2, and n-butyllithium/hexanes 1.6 M (19.8 ml, 31.7 mmol) was added over approximately 1 h while stirring. The solution initially turned from colorless to light yellow, then to milky white. After 2 h, at -78 °C, PCl3 (0.80 ml, 9.17 mmol) was added over a period of 15 minutes. When the PCl3 was added, the solution turned orange-red. The solution was kept at -78 °C for another 1 h. Then the solution was allowed to come to room temperature over 1 h. The solvent was evaporated, leaving the crude acetal, which was dissolved in a mixture of dichloromethane and water. The solution was then washed: first with concentrated NaHCO3 and then with brine. The organic phase was dried over Na2SO4. The organic phase was then evaporated, leaving a residue (5.24 g). The crude material was dissolved in 50 ml THF and 50 ml 2 M HCl. The solution was stirred under reflux conditions for 1 h under a stream of N2. To the solution, 50 ml of water and 50 ml of ethyl acetate were added. The organic phase was then washed, first with concentrated NaHCO3 and then with brine, dried over Na2SO4 and evaporated, leaving a residue (3.97 g). This residue, which is crude tris(4-formylphenyl)phosphane and tris(4-formylphenyl)phosphane oxide (I), was dissolved in 25% CHCl3/ 75% ethyl acetate and applied to a silica gel column with 25% CHCl3/ 75% ethyl acetate as the mobile phase. The column was run as a flash column. This process yielded pure tris(4-formylphenyl)phosphane, 1.51 g, 44% yield. Continuing to run the flash column produced pure tris(4-formylphenyl)phosphane oxide (I),1.92 g, 56% yield. Crystals of (I) were prepared by evaporation of a solution in THF over one week.

Refinement top

H atoms were placed in idealized positions with C—H distances 0.95 - 0.99 Å and thereafter treated as riding. Uiso for H was assigned as 1.2 times Ueq of the attached C atoms. The THF molecule is disordered about a twofold axis, and its atoms were assigned half occupancy.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Numbering scheme and ellipsoids at the 50% level. H atoms are represented with arbitrary radius. Only one orientation of the disordered solvent molecule is shown.
Tris(4-formylphenyl)phosphane oxide tetrahydrofuran hemisolvate top
Crystal data top
C21H15O4P·0.5C4H8OF(000) = 1664
Mr = 398.35Dx = 1.385 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7492 reflections
a = 21.371 (3) Åθ = 2.5–33.7°
b = 13.474 (2) ŵ = 0.17 mm1
c = 13.436 (2) ÅT = 110 K
β = 99.018 (9)°Fragment, yellow
V = 3821.1 (10) Å30.45 × 0.43 × 0.38 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
7598 independent reflections
Radiation source: fine-focus sealed tube5928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω and ϕ scansθmax = 33.7°, θmin = 3.0°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 3333
Tmin = 0.926, Tmax = 0.937k = 1921
36155 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0523P)2 + 2.5619P]
where P = (Fo2 + 2Fc2)/3
7598 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C21H15O4P·0.5C4H8OV = 3821.1 (10) Å3
Mr = 398.35Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.371 (3) ŵ = 0.17 mm1
b = 13.474 (2) ÅT = 110 K
c = 13.436 (2) Å0.45 × 0.43 × 0.38 mm
β = 99.018 (9)°
Data collection top
Nonius KappaCCD
diffractometer
7598 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
5928 reflections with I > 2σ(I)
Tmin = 0.926, Tmax = 0.937Rint = 0.023
36155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.03Δρmax = 0.40 e Å3
7598 reflectionsΔρmin = 0.39 e Å3
280 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.328736 (12)0.285691 (19)0.269566 (19)0.01652 (7)
O10.27730 (4)0.35710 (6)0.23209 (6)0.02304 (16)
O20.58557 (5)0.58191 (7)0.41717 (7)0.0341 (2)
O30.21889 (4)0.06198 (6)0.57196 (7)0.02736 (18)
O40.42853 (5)0.02731 (8)0.07657 (8)0.0385 (2)
C10.40140 (5)0.34656 (8)0.32453 (7)0.01777 (18)
C20.40518 (5)0.44958 (8)0.31497 (8)0.02015 (19)
H20.36910.48610.28480.024*
C30.46164 (5)0.49869 (8)0.34949 (8)0.0224 (2)
H30.46430.56870.34250.027*
C40.51435 (5)0.44465 (8)0.39446 (8)0.02102 (19)
C50.51021 (5)0.34239 (9)0.40684 (8)0.0227 (2)
H50.54590.30630.43930.027*
C60.45398 (5)0.29303 (8)0.37179 (8)0.0217 (2)
H60.45120.22320.37980.026*
C70.57583 (6)0.49462 (10)0.42927 (9)0.0268 (2)
H70.60960.45560.46320.032*
C80.30889 (5)0.20142 (7)0.36429 (7)0.01710 (17)
C90.26866 (5)0.12078 (8)0.33428 (8)0.01918 (19)
H90.25430.10920.26470.023*
C100.24976 (5)0.05794 (8)0.40579 (8)0.01975 (19)
H100.22300.00290.38550.024*
C110.27051 (5)0.07641 (8)0.50828 (8)0.01879 (18)
C120.30915 (5)0.15758 (8)0.53806 (8)0.0211 (2)
H120.32230.17030.60780.025*
C130.32874 (5)0.22025 (8)0.46671 (8)0.01944 (18)
H130.35540.27530.48730.023*
C140.25276 (5)0.01018 (8)0.58758 (8)0.0222 (2)
H140.26920.02550.65570.027*
C150.35007 (5)0.21019 (7)0.16835 (7)0.01758 (18)
C160.39073 (5)0.12789 (8)0.18493 (8)0.0216 (2)
H160.40740.10810.25170.026*
C170.40635 (6)0.07555 (9)0.10328 (9)0.0244 (2)
H170.43480.02110.11410.029*
C180.38019 (5)0.10291 (9)0.00515 (8)0.0234 (2)
C190.34019 (5)0.18443 (9)0.01138 (8)0.0236 (2)
H190.32280.20310.07820.028*
C200.32550 (5)0.23890 (8)0.07013 (8)0.02047 (19)
H200.29880.29550.05880.025*
C210.39321 (6)0.04313 (10)0.08199 (9)0.0303 (3)
H210.37220.06160.14690.036*
O1S0.45041 (11)0.23429 (19)0.84831 (19)0.0494 (6)0.50
C1S0.51269 (14)0.1940 (3)0.8648 (3)0.0386 (6)0.50
H11S0.51700.14480.92020.058*0.50
H12S0.54430.24730.88310.058*0.50
C2S0.5231 (3)0.1445 (4)0.7670 (3)0.0762 (15)0.50
H21S0.56780.14980.75650.114*0.50
H22S0.51040.07380.76520.114*0.50
C3S0.4797 (3)0.2050 (3)0.6906 (4)0.0720 (16)0.50
H31S0.50120.26560.67150.108*0.50
H32S0.46480.16570.62920.108*0.50
C4S0.4278 (2)0.2296 (4)0.7434 (3)0.0701 (14)0.50
H41S0.40940.29440.71960.105*0.50
H42S0.39430.17860.72980.105*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01646 (12)0.01632 (11)0.01603 (11)0.00020 (9)0.00027 (8)0.00027 (9)
O10.0221 (4)0.0220 (4)0.0238 (4)0.0043 (3)0.0003 (3)0.0014 (3)
O20.0340 (5)0.0338 (5)0.0348 (5)0.0149 (4)0.0062 (4)0.0057 (4)
O30.0300 (4)0.0246 (4)0.0285 (4)0.0029 (3)0.0075 (3)0.0020 (3)
O40.0330 (5)0.0477 (6)0.0363 (5)0.0048 (4)0.0103 (4)0.0206 (4)
C10.0174 (4)0.0189 (4)0.0169 (4)0.0015 (3)0.0024 (3)0.0020 (3)
C20.0220 (5)0.0203 (4)0.0182 (4)0.0007 (4)0.0032 (3)0.0007 (4)
C30.0260 (5)0.0209 (5)0.0209 (4)0.0049 (4)0.0050 (4)0.0006 (4)
C40.0196 (5)0.0259 (5)0.0183 (4)0.0045 (4)0.0052 (3)0.0043 (4)
C50.0176 (5)0.0259 (5)0.0244 (5)0.0008 (4)0.0021 (4)0.0037 (4)
C60.0201 (5)0.0197 (5)0.0249 (5)0.0004 (4)0.0015 (4)0.0024 (4)
C70.0223 (5)0.0335 (6)0.0253 (5)0.0075 (4)0.0059 (4)0.0076 (5)
C80.0164 (4)0.0176 (4)0.0172 (4)0.0005 (3)0.0021 (3)0.0003 (3)
C90.0196 (5)0.0209 (4)0.0166 (4)0.0014 (4)0.0014 (3)0.0033 (3)
C100.0193 (4)0.0190 (4)0.0210 (4)0.0022 (4)0.0035 (3)0.0027 (4)
C110.0202 (4)0.0177 (4)0.0190 (4)0.0018 (3)0.0049 (3)0.0010 (3)
C120.0251 (5)0.0215 (5)0.0162 (4)0.0001 (4)0.0017 (4)0.0019 (3)
C130.0208 (5)0.0186 (4)0.0182 (4)0.0019 (4)0.0008 (3)0.0025 (3)
C140.0263 (5)0.0210 (5)0.0206 (5)0.0026 (4)0.0076 (4)0.0006 (4)
C150.0177 (4)0.0187 (4)0.0159 (4)0.0024 (3)0.0012 (3)0.0008 (3)
C160.0242 (5)0.0221 (5)0.0180 (4)0.0012 (4)0.0012 (4)0.0007 (4)
C170.0242 (5)0.0250 (5)0.0239 (5)0.0005 (4)0.0037 (4)0.0053 (4)
C180.0229 (5)0.0287 (5)0.0192 (4)0.0076 (4)0.0053 (4)0.0064 (4)
C190.0231 (5)0.0311 (5)0.0160 (4)0.0066 (4)0.0009 (4)0.0004 (4)
C200.0197 (4)0.0230 (5)0.0177 (4)0.0028 (4)0.0001 (3)0.0013 (4)
C210.0289 (6)0.0398 (7)0.0235 (5)0.0105 (5)0.0086 (4)0.0111 (5)
O1S0.0330 (11)0.0568 (14)0.0539 (14)0.0007 (10)0.0072 (10)0.0064 (11)
C1S0.0297 (13)0.0431 (17)0.0399 (16)0.0004 (11)0.0043 (12)0.0067 (14)
C2S0.107 (5)0.078 (3)0.039 (2)0.021 (3)0.001 (2)0.008 (2)
C3S0.128 (5)0.0307 (17)0.046 (2)0.003 (2)0.022 (3)0.0030 (17)
C4S0.070 (3)0.078 (3)0.050 (2)0.030 (2)0.0275 (19)0.036 (2)
Geometric parameters (Å, º) top
P1—O11.4880 (8)C12—H120.9500
P1—C81.8050 (10)C13—H130.9500
P1—C11.8083 (11)C14—H140.9500
P1—C151.8129 (10)C15—C201.3963 (14)
O2—C71.2099 (16)C15—C161.4050 (15)
O3—C141.2107 (14)C16—C171.3882 (15)
O4—C211.2078 (17)C16—H160.9500
C1—C21.3975 (15)C17—C181.3984 (16)
C1—C61.4009 (15)C17—H170.9500
C2—C31.3905 (15)C18—C191.3881 (17)
C2—H20.9500C18—C211.4830 (16)
C3—C41.3968 (16)C19—C201.3944 (15)
C3—H30.9500C19—H190.9500
C4—C51.3924 (16)C20—H200.9500
C4—C71.4851 (15)C21—H210.9500
C5—C61.3895 (15)O1S—C4S1.418 (4)
C5—H50.9500O1S—C1S1.422 (4)
C6—H60.9500C1S—C2S1.519 (5)
C7—H70.9500C1S—H11S0.9900
C8—C131.3981 (14)C1S—H12S0.9900
C8—C91.4049 (14)C2S—C3S1.510 (6)
C9—C101.3873 (15)C2S—H21S0.9900
C9—H90.9500C2S—H22S0.9900
C10—C111.4013 (14)C3S—C4S1.446 (8)
C10—H100.9500C3S—H31S0.9900
C11—C121.3909 (15)C3S—H32S0.9900
C11—C141.4839 (15)C4S—H41S0.9900
C12—C131.3904 (15)C4S—H42S0.9900
O1—P1—C8113.74 (5)C11—C14—H14117.6
O1—P1—C1112.73 (5)C20—C15—C16120.01 (10)
C8—P1—C1106.20 (5)C20—C15—P1116.88 (8)
O1—P1—C15111.61 (5)C16—C15—P1123.09 (8)
C8—P1—C15106.89 (5)C17—C16—C15119.67 (10)
C1—P1—C15105.07 (5)C17—C16—H16120.2
C2—C1—C6119.95 (10)C15—C16—H16120.2
C2—C1—P1118.12 (8)C16—C17—C18120.06 (11)
C6—C1—P1121.87 (8)C16—C17—H17120.0
C3—C2—C1120.11 (10)C18—C17—H17120.0
C3—C2—H2119.9C19—C18—C17120.31 (10)
C1—C2—H2119.9C19—C18—C21119.37 (11)
C2—C3—C4119.68 (10)C17—C18—C21120.29 (11)
C2—C3—H3120.2C18—C19—C20119.97 (10)
C4—C3—H3120.2C18—C19—H19120.0
C5—C4—C3120.36 (10)C20—C19—H19120.0
C5—C4—C7118.73 (11)C19—C20—C15119.93 (10)
C3—C4—C7120.91 (10)C19—C20—H20120.0
C6—C5—C4120.07 (10)C15—C20—H20120.0
C6—C5—H5120.0O4—C21—C18124.90 (12)
C4—C5—H5120.0O4—C21—H21117.6
C5—C6—C1119.79 (10)C18—C21—H21117.6
C5—C6—H6120.1C4S—O1S—C1S107.6 (3)
C1—C6—H6120.1O1S—C1S—C2S107.0 (3)
O2—C7—C4124.11 (12)O1S—C1S—H11S110.3
O2—C7—H7117.9C2S—C1S—H11S110.3
C4—C7—H7117.9O1S—C1S—H12S110.3
C13—C8—C9120.03 (9)C2S—C1S—H12S110.3
C13—C8—P1120.75 (8)H11S—C1S—H12S108.6
C9—C8—P1119.01 (7)C3S—C2S—C1S101.2 (4)
C10—C9—C8120.31 (9)C3S—C2S—H21S111.5
C10—C9—H9119.8C1S—C2S—H21S111.5
C8—C9—H9119.8C3S—C2S—H22S111.5
C9—C10—C11119.38 (10)C1S—C2S—H22S111.5
C9—C10—H10120.3H21S—C2S—H22S109.4
C11—C10—H10120.3C4S—C3S—C2S103.1 (4)
C12—C11—C10120.30 (10)C4S—C3S—H31S111.2
C12—C11—C14118.26 (9)C2S—C3S—H31S111.2
C10—C11—C14121.44 (10)C4S—C3S—H32S111.2
C13—C12—C11120.57 (9)C2S—C3S—H32S111.2
C13—C12—H12119.7H31S—C3S—H32S109.1
C11—C12—H12119.7O1S—C4S—C3S109.3 (3)
C12—C13—C8119.39 (10)O1S—C4S—H41S109.8
C12—C13—H13120.3C3S—C4S—H41S109.8
C8—C13—H13120.3O1S—C4S—H42S109.8
O3—C14—C11124.87 (10)C3S—C4S—H42S109.8
O3—C14—H14117.6H41S—C4S—H42S108.3
O1—P1—C1—C28.16 (10)C14—C11—C12—C13178.05 (10)
C8—P1—C1—C2133.35 (8)C11—C12—C13—C80.44 (16)
C15—P1—C1—C2113.60 (9)C9—C8—C13—C121.05 (16)
O1—P1—C1—C6174.63 (8)P1—C8—C13—C12175.71 (8)
C8—P1—C1—C649.43 (10)C12—C11—C14—O3179.01 (11)
C15—P1—C1—C663.62 (10)C10—C11—C14—O31.64 (17)
C6—C1—C2—C31.99 (16)O1—P1—C15—C2011.07 (10)
P1—C1—C2—C3175.28 (8)C8—P1—C15—C20136.02 (8)
C1—C2—C3—C40.51 (15)C1—P1—C15—C20111.41 (9)
C2—C3—C4—C51.42 (16)O1—P1—C15—C16170.73 (9)
C2—C3—C4—C7178.15 (10)C8—P1—C15—C1645.78 (10)
C3—C4—C5—C61.87 (16)C1—P1—C15—C1666.79 (10)
C7—C4—C5—C6177.70 (10)C20—C15—C16—C170.10 (16)
C4—C5—C6—C10.39 (16)P1—C15—C16—C17178.04 (8)
C2—C1—C6—C51.54 (16)C15—C16—C17—C181.91 (17)
P1—C1—C6—C5175.63 (8)C16—C17—C18—C192.16 (17)
C5—C4—C7—O2175.74 (11)C16—C17—C18—C21175.80 (11)
C3—C4—C7—O23.83 (17)C17—C18—C19—C200.57 (17)
O1—P1—C8—C1397.60 (9)C21—C18—C19—C20177.40 (10)
C1—P1—C8—C1326.97 (10)C18—C19—C20—C151.24 (16)
C15—P1—C8—C13138.76 (9)C16—C15—C20—C191.48 (16)
O1—P1—C8—C977.11 (9)P1—C15—C20—C19179.73 (8)
C1—P1—C8—C9158.32 (8)C19—C18—C21—O4177.78 (12)
C15—P1—C8—C946.53 (9)C17—C18—C21—O44.24 (19)
C13—C8—C9—C101.68 (16)C4S—O1S—C1S—C2S11.3 (4)
P1—C8—C9—C10176.43 (8)O1S—C1S—C2S—C3S28.0 (4)
C8—C9—C10—C110.82 (16)C1S—C2S—C3S—C4S33.6 (5)
C9—C10—C11—C120.67 (16)C1S—O1S—C4S—C3S11.4 (4)
C9—C10—C11—C14178.66 (10)C2S—C3S—C4S—O1S29.0 (5)
C10—C11—C12—C131.31 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O3i0.952.563.4303 (16)152
C14—H14···O1ii0.952.503.1575 (14)127
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O3i0.952.563.4303 (16)152
C14—H14···O1ii0.952.503.1575 (14)127
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z+1.
 

Footnotes

Current address: Natural Science Department, Clearwater Campus, St Petersburg College, PO Box 13489, St Petersburg, FL 33733-3489, USA.

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. This work was supported in part by the US Department of Energy (DE—FG02–01ER15267).

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Volume 69| Part 8| August 2013| Pages o1362-o1363
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