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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 60| Part 7| July 2004| Pages o475-o478
doi:10.1107/S0108270104012211

Partially oxidized {2-[(benzoyl­methyl­ene)­di­phenyl-λ5-phosphino]­ethyl}di­phenyl­phosphine as a monohydrate

CROSSMARK_Color_square_no_text.svg
E. Mothi Mohamed,a Krishnaswamy Panchanatheswaran,a John N. Lowb‡ and Christopher Glidewellc*

aDepartment of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 18 May 2004; accepted 19 May 2004; online 22 June 2004)

The title compound is a co-crystal of {2-[(benzoyl­methyl­ene)­di­phenyl-λ5-phosphino]­ethyl}di­phenyl­phosphine oxide, {2-[(benzoyl­methyl­ene)­di­phenyl-λ5-phosphino]­ethyl}di­phenyl­phosphine and water in an approximate 2:1:3 ratio, with an overall composition of C34H30O1.678P2·H2O. The yl­idic portion shows the expected electronic polarization, and the organic components are linked by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds.

Comment

The title compound, (I[link]), is a co-crystallized mixture of the phosphine oxide (II[link]) and the phosphine (III[link]) obtained as an unexpected product during the attempted crystallization of (III[link]). Form (II[link]), as the monohydrate, was taken as the basis of the refinement model, and the occupancy of atom site O2, bonded to P2 (Fig. 1[link]), refined to 0.678 (7). Since the overall molecular size and shape is dominated by the disposition of the phenyl groups, the phosphine and its oxide readily occupy similar spaces in the crystal, leading to co-crystallization. It is possible that the occupancy of the O2 site may vary slightly from one crystal to another.

The central C21—P1—C1—C2—P2—C41 fragment of (I[link]) is nearly planar, with an extended chain conformation, as shown by the key torsion angles (Table 1[link]), and bonds P1—C17 and P2—O2 are both synclinal bond C1—C2. The locations of atoms C17 and O2, as well as the torsion angles of the phenyl rings about the P—C bonds, preclude the possibility of any internal molecular symmetry. The P1—C17—C19(—O18)—C11 fragment is effectively planar.

The inter-bond angles at both P1 and P2 show considerable variation from the ideal tetrahedral values (Table 1[link]). That the two angles O2—P2—C41 and O2—P2—C51, involving the ipso-C atoms of the phenyl rings, are almost identical, while the angles C17—P1—C21 and C17—P1—C31, also involving ipso-C atoms, differ by almost 10°, points to some subtle intra- or intermolecular factors which are not immediately apparent. The angles P1—C17—C18 and C17—C18—O18 in the yl­idic portion are both significantly greater than 120°.

[Scheme 1]

The bond distances involving the P atoms, other than P1—C17, are typical of their types (Allen et al., 1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). The bond-length compilation of Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]) does not include any data derived from phosphorus yl­ides. However, Aitken et al. (2000[Aitken, R. A., Karodia, N. & Lightfoot, P. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 333-340.]) have recently surveyed and tabulated the structural properties of oxo-stabilized phosphorus yl­ides using data retrieved from the Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For neutral yl­ides of the type Ph3P=CαR(Cβ­OR′), the ranges of the P—Cα, Cα—Cβ and Cβ—O distances were found to be 1.708–1.773, 1.333–1.435 and 1.226–1.301 Å, respectively. These ranges may be compared and contrasted with the P—CH2 distances of 1.674 (2) and 1.666 (2) Å found for the two independent mol­ecules in Ph3P=CH2 (Schmidbaur et al., 1989[Schmidbaur, H., Jeong, J., Schier, A., Graf, W., Wilkinson, D. L., Muller, G. & Kruger, C. (1989). New J. Chem. 13, 3441-352.]), and with the average C—C and C—O distances of 1.465 and 1.222 Å in the conjugated fragment =C—C=O (Allen et al., 1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). The corresponding values observed in compound (I[link]) (Table 1[link]) are all thus comfortably within the ranges recently reported (Aitken et al., 2000[Aitken, R. A., Karodia, N. & Lightfoot, P. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 333-340.]) and indicate that the charge-separated form (IIa[link]) is an important contributor to the overall molecular–electronic structure, alongside the classically localized form (II[link]) (see scheme).

Compound (I[link]) crystallizes as the monohydrate and the water mol­ecule is linked to the negatively polarized atom O18 via an O—H⋯O hydrogen bond (Table 2[link]). The water mol­ecule plays no other role in the intermolecular aggregation, as there are no potential donors or acceptors of hydrogen bonds within a suitable distance of atom O1.

The organic mol­ecules in (I[link]) are, however, linked by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds (Table 2[link]). Atoms C26 and C45 in the mol­ecule at (x, y, z) act as hydrogen-bond donors to, respectively, ring C41–C46 in the mol­ecule at (x − 1, y, z) and ring C11–C16 in the mol­ecule at (1 + x, y, z), so generating by translation a chain of rings running parallel to the [100] direction (Fig. 2[link]). In addition, atom C12 in the mol­ecule at (x, y, z) acts as donor to ring C31–C36 in the mol­ecule at (−x, 1 − y, −z), so forming a cyclic centrosymmetric dimer centred at (0, [{1 \over 2}], 0) (Fig. 3[link]), and this motif serves to link the molecular ladders in pairs.

The C—H⋯O hydrogen bonds in (I[link]) both involve atom O2 as the acceptor and their overall effect is thus complicated somewhat by the partial occupancy of the O2 site. We consider first the outcome of these interactions assuming full occupancy of the O2 site, followed by the effects of partial occupancy. Atoms C1, adjacent to positively polarized atom P1, and C32 in the mol­ecule at (x, y, z) both act as hydrogen-bond donors to atom O2 in the mol­ecule at (1 − x, 2 − y, −z). With full occupancy at O2, these interactions would generate a cyclic centrosymmetric dimer, centred at ([{1 \over 2}], 1, 0), in which an R22(16) ring (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) containing atom C32 is divided into one R22(10) segment (Fig. 4[link]) and two R21(7) segments (Fig. 4[link]). With an occupancy of the O2 site of 0.678 (7), ca 46% of these molecular pairs will contain two atoms of type O2, ca 44% will contain just one atom of type O2 and ca 10% will contain no O2 atoms. Hence, ca 90% of these molecular pairs are internally linked by hydrogen bonds. In the event of full occupancy of the O2 site, this motif (Fig. 4[link]) would serve to link the paired [100] ladders into an (001) sheet. Despite the presence of five independent phenyl rings, aromatic π–π stacking interactions are absent from the crystal structure of (I[link]).

[Figure 1]
Figure 1
A view of the independent components of (I[link]), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Atom site O2 has an occupancy of 0.678 (7) (see text).
[Figure 2]
Figure 2
A stereoview of part of the crystal structure of (I[link]), showing the formation of a [100] chain of rings generated by C—H⋯π(arene) hydrogen bonds. For the sake of clarity, the water mol­ecule and the H atoms not involved in the motif shown have been omitted.
[Figure 3]
Figure 3
Part of the crystal structure of (I[link]), showing the formation of a C—H⋯π(arene) hydrogen-bonded dimer centred at (0, [{1 \over 2}], 0). For the sake of clarity, the water mol­ecule and the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (−x, 1 − y, −z).
[Figure 4]
Figure 4
Part of the crystal structure of (I[link]), showing the formation of a C—H⋯O hydrogen-bonded dimer centred at ([{1 \over 2}], 1, 0). For the sake of clarity, the water mol­ecule and the H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 2 − y, −z). Atom site O2 has an occupancy of 0.678 (7) (see text).

Experimental

The yl­ide (III[link]) (see scheme) was prepared by the action of triethyl­amine on the corresponding phospho­nium salt (Oosawa et al., 1976[Oosawa, Y., Urabe, H., Saito, T. & Sasaki, Y. (1976). J. Organomet. Chem. 122, 113-121.]); IR (ν, cm−1): 1526 (C=O). The title compound, (I[link]), was formed as crystals suitable for single-crystal X-ray diffraction by the vapour diffusion of light petroleum into a benzene solution of yl­ide (III[link]) under aerobic conditions; IR (ν, cm−1): 1514 (C=O), 1193 (P=O).

Crystal data

  • C34H30O1.68P2·H2O

  • Mr = 545.38

  • Triclinic, [P\overline 1]

  • a = 9.1392 (4) Å

  • b = 11.8931 (3) Å

  • c = 13.6025 (5) Å

  • α = 105.725 (2)°

  • β = 92.472 (2)°

  • γ = 101.934 (2)°

  • V = 1384.67 (9) Å3

  • Z = 2

  • Dx = 1.308 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 6257 reflections

  • θ = 3.1–27.5°

  • μ = 0.19 mm−1

  • T = 120 (2) K

  • Plate, colourless

  • 0.16 × 0.12 × 0.05 mm
Data collection

  • Nonius KappaCCD diffractometer

  • φ scans, and ω scans with κ offsets

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-37.], 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.955, Tmax = 0.991

  • 21 189 measured reflections

  • 6257 independent reflections

  • 4739 reflections with I > 2σ(I)

  • Rint = 0.137

  • θmax = 27.5°

  • h = −11 → 11

  • k = −15 → 15

  • l = −17 → 17
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.143

  • S = 1.06

  • 6257 reflections

  • 353 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.05P)2 + 1.1826P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.70 e Å−3

Table 1
Selected geometric parameters (Å, °)

P1—C1 1.817 (2) 
P1—C21 1.807 (2)
P1—C31 1.801 (2)
P2—C2 1.808 (2)
P2—C41 1.809 (2)
P2—C51 1.819 (2)
P1—C17 1.722 (2)
C17—C18 1.393 (3)
C18—O18 1.277 (3)
C18—C11 1.503 (3)
P2—O2 1.415 (2)
C1—P1—C17 114.73 (11)
C1—P1—C21 105.51 (10)
C1—P1—C31 106.67 (10)
C17—P1—C21 105.46 (10)
C17—P1—C31 115.03 (11)
C21—P1—C31 108.95 (10)
P1—C17—C18 125.76 (18)
C17—C18—O18 124.6 (2)
C2—P2—O2 117.61 (13)
C2—P2—C41 104.48 (11)
C2—P2—C51 105.72 (11)
O2—P2—C41 112.58 (13)
O2—P2—C51 111.94 (13)
C41—P2—C51 103.22 (10)
C11—C18—O18 117.7 (2)
C11—C18—C17 117.6 (2)
P1—C1—C2—P2 −169.97 (12)
C17—P1—C1—C2 77.30 (18)
C21—P1—C1—C2 −167.09 (16)
C31—P1—C1—C2 −51.31 (18)
O2—P2—C2—C1 −59.4 (2)
C41—P2—C2—C1 174.93 (16)
C51—P2—C2—C1 66.39 (18)
C1—P1—C17—C18 −59.1 (2)
P1—C17—C18—C11 175.31 (17)
C17—C18—C11—C12 34.7 (3)
C1—P1—C21—C22 123.45 (19)
C1—P1—C31—C32 −42.2 (2)
C2—P2—C41—C42 148.40 (18)
C2—P2—C51—C52 −142.77 (18)

Table 2
Hydrogen-bonding geometry (Å, °)

Cg1, Cg3 and Cg4 are the centroids of rings C11–C16, C31–C36 and C41–C46, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1C⋯O18 0.95 1.83 2.783 (3) 175
C1—H1A⋯O2i 0.99 2.18 3.147 (4) 166
C32—H32⋯O2i 0.95 2.36 3.298 (4) 168
C12—H12⋯Cg3ii 0.95 2.87 3.777 (3) 159
C26—H26⋯Cg4iii 0.95 2.97 3.757 (3) 141
C45—H45⋯Cg1iv 0.95 2.77 3.589 (3) 145
Symmetry codes: (i) 1-x,2-y,-z; (ii) -x,1-y,-z; (iii) x-1,y,z; (iv) 1+x,y,z.

Crystals of (I[link]) are triclinic; space group P[\overline 1] was selected and confirmed by the subsequent analysis. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 (CH) or 0.99 Å (CH2) and O—H distances of 0.95 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O). It was apparent from an early stage that the occupancy of the O2 site was less than unity; the refined value of the site-occupancy factor was 0.678 (7).

Data collection: KappaCCD Server Software (Nonius, 1997[Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO–SMN (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–SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270104012211/sk1734sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104012211/sk1734Isup2.hkl


Comment top

The title compound, (I), is a co-crystallized mixture of the phosphine oxide, (II), and the phosphine, (III), obtained as an unexpected product during the attempted crystallization of (III). Form (II), as the monohydrate, was taken as the basis of the refinement model, and the occupancy of the atom site O2, bonded to P2 (Fig.1), refined to 0.678 (7). Since the overall molecular size and shape is dominated by the disposition of the phenyl groups, the phosphine and its oxide readily occupy similar spaces in the crystal, leading to co-crystallization. It is possible that the occupancy of the O2 site may vary slightly from one crystal to another. \sch

The central fragment C21—P1—C1—C2—P2—C41 is nearly planar, with an extended-chain conformation, as shown by the key torsion angles (Table 1), and the bonds P1—C17 and P2—O2 are both synclinal to the bond C1—C2. The locations of atoms C17 and O2, as well as the torsion angles of the phenyl rings about the P—C bonds, preclude the possibility of any internal molecular symmetry. The fragment P1—C17—C19(–O18)—C11 is effectively planar.

The inter-bond angles at both P1 and P2 show considerable variation from the ideal tetrahedral values (Table 1). That the two angles O2—P2—C41 and O2—P2—C51, involving the ipso C atoms of phenyl rings, are almost identical, while the angles C17—P1—C21 and C17—P1—C31, also involving ipso C atoms, differ by almost 10°, points to some subtle intra- or intermolecular factors which are not immediately apparent. The angles P1—C17—C18 and C17—C18—O18 in the ylidic portion are both significantly greater than 120°.

The bond distances involving the P atoms, other than P1—C17, are typical of their types (Allen et al., 1987). The bond-length compilation of Allen et al. (1987) does not include any data derived from phosphorus ylides. However, Aitken et al. (2000) have recently surveyed and tabulated the structural properties of oxo-stabilized phosphorus ylides using data retrieved from the Cambridge Structural Database (Version?; Allen, 2002). For neutral ylides of the type Ph3P═CαR(CβOR'), the ranges of the P—Cα, Cα—Cβ and Cβ—O distances were found to be 1.708–1.773, 1.333–1.435 and 1.226–1.301 Å, respectively. These ranges may be compared and contrasted with the P—CH2 distances of 1.674 (2) and 1.666 (2) Å found for the two independent molecules in Ph3P═CH2 (Schmidbaur et al., 1989), and with the average C—C and C—O distances of 1.465 and 1.222 Å in the conjugated fragment ═C—C═O (Allen et al., 1987). The corresponding values observed in compound (I) (Table 1) are all thus comfortably within the ranges recently reported (Aitken et al., 2000), and indicate that the charge-separated form (IIa) is an important contributor to the overall molecular-electronic structure, alongside the classically localized form (II).

Compound (I) crystallizes as the monohydrate and the water molecule is linked to the negatively polarized atom O18 via an O—H···O hydrogen bond (Table 2). The water molecule plays no other role in the intermolecular aggregation, as there are no potential donors or acceptors of hydrogen bonds within suitable distance of atom O1.

The organic molecules are, however, linked by a combination of C—H···O and C—H···π(arene) hydrogen bonds (Table 2). Atoms C26 and C45 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, ring C41—C46 in the molecule at (x − 1, y, z) and ring C11—C16 in the molecule at (1 + x, y, z), so generating by translation a chain of rings running parallel to the [100] direction (Fig. 2). In addition, atom C12 in the molecule at (x, y, z) acts as donor to ring C31—C36 in the molecule at (-x, 1 − y, −z), so forming a cyclic centrosymmetric dimer centred at (0, 1/2, 0) (Fig. 3), and this motif serves to link the molecular ladders in pairs.

The C—H···O hydrogen bonds in (I) both involve atom O2 as the acceptor and their overall effect is thus complicated somewhat by the partial occupancy of the O2 site. We consider first the outcome of these interactions assuming full occupancy of the O2 site, followed by the effects of the partial occupancy. The atoms C1, adjacent to the positively polarized atom P1, and C32 in the molecule at (x, y, z) both act as hydrogen-bond donors to atom O2 in the molecule at (1 − x, 2 − y, −z). With full occupancy at O2, these interactions would generate a cyclic centrosymmetric dimer, centred at (1/2, 1, 0), in which an R22(16) ring (Bernstein at al., 1995) containing atom C32 is divided into one R22(10) and two R21(7) segments (Fig. 4). With an occupancy of the O2 site of 0.678 (7), ca 46% of these molecular pairs will contain two atoms of type O2, ca 44% will contain just one atom of type O2 and ca 10% will contain no O2 atoms. Hence ca 90% of these molecular pairs are internally linked by hydrogen bonds. In the event of full occupancy of the O2 site, this motif (Fig. 4) would serve to link the paired [100] ladders into an (001) sheet. Despite the presence of five independent phenyl rings, aromatic π–π stacking interactions are absent from the crystal structure of (I).

Table 2. Hydrogen-bond parameters (Å, °) for (I). Cg1, Cg3 and Cg4 are the centroids of rings C11—C16, C31—C36 and C41—C46, respectively.

Experimental top

The ylide (III) was prepared by the action of triethylamine on the corresponding phosphonium salt (Oosawa et al., 1976); IR (ν, cm−1): 1526 (C═O). The title compound, (I), was formed as crystals suitable for single-crystal X-ray diffraction by the vapour diffusion of light petroleum into a benzene solution of ylide (III) under aerobic conditions; IR (ν, cm−1): 1514 (C═O), 1193 (P═O).

Refinement top

Crystals of (I) are triclinic; space group P1 was selected and confirmed by the subsequent analysis. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 (CH) or 0.99 Å (CH2) and O—H distances of 0.95 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O). It was apparent from an early stage that the occupancy of the O2 site was less than unity; the refined value of the site-occupancy factor was 0.678 (7).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The atom site O2 has occupancy 0.678 (7) (see text).
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing formation of a [100] chain of rings generated by C—H···π(arene) hydrogen bonds. For the sake of clarity, the water molecule and the H atoms not involved in the motif shown have been omitted.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing formation of a C—H···π(arene) hydrogen-bonded dimer centred at (0, 1/2, 0). For the sake of clarity, the water molecule and the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (-x, 1 − y, −z).
[Figure 4] Fig. 4. Part of the crystal structure of (I), showing formation of a C—H···O hydrogen-bonded dimer centred at (1/2, 1, 0). For the sake of clarity, the water molecule and the H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 2 − y, −z). The atom site O2 has occupancy 0.678 (7) (see text).
{2-[(benzoylmethylene)diphenyl-λ5-phosphino]ethyl}diphenylphosphine monohydrate top
Crystal data top
C34H30O1.68P2·H2OZ = 2
Mr = 545.38F(000) = 574.8
Triclinic, P1Dx = 1.308 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1392 (4) ÅCell parameters from 6257 reflections
b = 11.8931 (3) Åθ = 3.1–27.5°
c = 13.6025 (5) ŵ = 0.19 mm−1
α = 105.725 (2)°T = 120 K
β = 92.472 (2)°Plate, colourless
γ = 101.934 (2)°0.16 × 0.12 × 0.05 mm
V = 1384.67 (9) Å3
Data collection top
Nonius KappaCCD
diffractometer		6257 independent reflections
Radiation source: rotating anode4739 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.137
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)		h = −11→11
Tmin = 0.955, Tmax = 0.991k = −15→15
21189 measured reflectionsl = −17→17
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.05P)2 + 1.1826P]
where P = (Fo2 + 2Fc2)/3
6257 reflections(Δ/σ)max < 0.001
353 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.70 e Å−3
Crystal data top
C34H30O1.68P2·H2Oγ = 101.934 (2)°
Mr = 545.38V = 1384.67 (9) Å3
Triclinic, P1Z = 2
a = 9.1392 (4) ÅMo Kα radiation
b = 11.8931 (3) ŵ = 0.19 mm−1
c = 13.6025 (5) ÅT = 120 K
α = 105.725 (2)°0.16 × 0.12 × 0.05 mm
β = 92.472 (2)°
Data collection top
Nonius KappaCCD
diffractometer		6257 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)		4739 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.991Rint = 0.137
21189 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å−3
6257 reflectionsΔρmin = −0.70 e Å−3
353 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.18580 (6)0.73418 (5)0.05959 (4)0.01716 (15)
P20.60170 (7)1.01348 (5)0.19183 (5)0.02323 (16)
O10.3943 (2)0.52924 (17)0.35852 (15)0.0392 (5)
O20.6390 (3)1.0848 (2)0.12456 (18)0.0252 (9)0.678 (7)
O180.32371 (18)0.68827 (16)0.25708 (13)0.0281 (4)
C10.3253 (2)0.8753 (2)0.09346 (17)0.0207 (5)
C20.4776 (2)0.8670 (2)0.13901 (18)0.0213 (5)
C110.0931 (3)0.6580 (2)0.33182 (18)0.0221 (5)
C12−0.0553 (3)0.5920 (2)0.31448 (18)0.0244 (5)
C13−0.1356 (3)0.5754 (2)0.3960 (2)0.0296 (6)
C14−0.0686 (3)0.6254 (3)0.4957 (2)0.0367 (6)
C150.0783 (3)0.6912 (3)0.51419 (19)0.0336 (6)
C160.1595 (3)0.7067 (2)0.43283 (18)0.0257 (5)
C170.1055 (3)0.6968 (2)0.16196 (17)0.0221 (5)
C180.1823 (3)0.6811 (2)0.24619 (17)0.0208 (5)
C210.0342 (2)0.7555 (2)−0.01810 (17)0.0181 (4)
C22−0.0166 (3)0.6814 (2)−0.11679 (18)0.0229 (5)
C23−0.1407 (3)0.6967 (2)−0.17046 (19)0.0300 (6)
C24−0.2118 (3)0.7882 (2)−0.1260 (2)0.0301 (6)
C25−0.1605 (3)0.8631 (2)−0.0283 (2)0.0287 (6)
C26−0.0381 (3)0.8468 (2)0.02628 (18)0.0238 (5)
C310.2720 (2)0.62300 (19)−0.01863 (16)0.0181 (4)
C320.3599 (3)0.6487 (2)−0.09478 (17)0.0210 (5)
C330.4249 (3)0.5621 (2)−0.15442 (18)0.0242 (5)
C340.4026 (3)0.4491 (2)−0.13845 (18)0.0248 (5)
C350.3156 (3)0.4233 (2)−0.06372 (19)0.0251 (5)
C360.2504 (2)0.5103 (2)−0.00306 (18)0.0214 (5)
C410.7656 (3)0.9844 (2)0.25110 (17)0.0212 (5)
C420.9043 (3)1.0604 (2)0.25247 (18)0.0244 (5)
C431.0331 (3)1.0474 (2)0.30313 (19)0.0282 (5)
C441.0230 (3)0.9582 (2)0.35124 (19)0.0277 (5)
C450.8859 (3)0.8815 (2)0.3495 (2)0.0283 (5)
C460.7578 (3)0.8945 (2)0.29957 (19)0.0246 (5)
C510.5156 (2)1.0892 (2)0.30114 (17)0.0210 (5)
C520.5246 (3)1.2106 (2)0.31965 (18)0.0256 (5)
C530.4659 (3)1.2743 (2)0.4042 (2)0.0319 (6)
C540.3996 (3)1.2151 (3)0.47173 (19)0.0321 (6)
C550.3905 (3)1.0942 (2)0.45410 (19)0.0274 (5)
C560.4461 (3)1.0295 (2)0.36834 (19)0.0251 (5)
H1A0.33990.90270.03130.025*
H1B0.28660.93640.14390.025*
H1C0.37360.58700.32660.059*
H1D0.36720.56520.42440.059*
H2A0.52560.81770.08480.026*
H2B0.46170.82670.19380.026*
H12−0.10220.55780.24610.029*
H13−0.23640.52970.38310.035*
H14−0.12350.61460.55140.044*
H150.12410.72600.58280.040*
H160.26100.75080.44620.031*
H17−0.00060.68600.16090.027*
H220.03340.6202−0.14770.027*
H23−0.17690.6448−0.23730.036*
H24−0.29580.7992−0.16290.036*
H25−0.20880.92570.00170.034*
H26−0.00360.89770.09370.029*
H320.37490.7257−0.10560.025*
H330.48460.5796−0.20620.029*
H340.44760.3898−0.17920.030*
H350.30000.3460−0.05350.030*
H360.19130.49260.04890.026*
H420.91131.12140.21880.029*
H431.12741.09990.30450.034*
H441.11070.94940.38570.033*
H450.87960.82000.38250.034*
H460.66380.84170.29840.029*
H520.57151.25120.27400.031*
H530.47121.35750.41570.038*
H540.36041.25810.53020.038*
H550.34581.05450.50100.033*
H560.43700.94560.35560.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0158 (3)0.0191 (3)0.0164 (3)0.0044 (2)0.0004 (2)0.0045 (2)
P20.0174 (3)0.0204 (3)0.0272 (3)0.0028 (2)0.0006 (2)0.0005 (2)
O10.0513 (12)0.0358 (11)0.0333 (10)0.0190 (9)0.0024 (9)0.0084 (8)
O20.0291 (15)0.0256 (15)0.0237 (14)0.0057 (10)0.0035 (10)0.0118 (11)
O180.0209 (8)0.0415 (11)0.0276 (9)0.0096 (7)0.0046 (7)0.0170 (8)
C10.0187 (11)0.0218 (12)0.0203 (11)0.0058 (9)−0.0002 (9)0.0034 (9)
C20.0181 (11)0.0212 (12)0.0225 (11)0.0041 (9)−0.0003 (9)0.0035 (9)
C110.0246 (12)0.0246 (12)0.0221 (11)0.0126 (9)0.0056 (9)0.0090 (9)
C120.0264 (12)0.0248 (12)0.0229 (11)0.0099 (10)0.0044 (10)0.0051 (10)
C130.0296 (13)0.0269 (13)0.0347 (14)0.0059 (10)0.0117 (11)0.0120 (11)
C140.0433 (16)0.0470 (17)0.0298 (14)0.0188 (13)0.0169 (12)0.0194 (13)
C150.0417 (15)0.0408 (16)0.0205 (12)0.0152 (12)0.0040 (11)0.0080 (11)
C160.0272 (12)0.0281 (13)0.0232 (12)0.0092 (10)0.0023 (10)0.0076 (10)
C170.0176 (11)0.0314 (13)0.0193 (11)0.0083 (9)0.0035 (9)0.0081 (10)
C180.0206 (11)0.0215 (12)0.0219 (11)0.0069 (9)0.0031 (9)0.0072 (9)
C210.0158 (10)0.0196 (11)0.0198 (11)0.0023 (8)0.0022 (8)0.0086 (9)
C220.0244 (12)0.0212 (12)0.0222 (11)0.0015 (9)0.0017 (9)0.0075 (9)
C230.0283 (13)0.0340 (14)0.0243 (12)−0.0027 (11)−0.0061 (10)0.0117 (11)
C240.0187 (11)0.0385 (15)0.0369 (14)−0.0010 (10)−0.0037 (10)0.0236 (12)
C250.0190 (12)0.0383 (15)0.0358 (14)0.0103 (11)0.0061 (10)0.0188 (12)
C260.0211 (11)0.0283 (13)0.0242 (12)0.0076 (10)0.0023 (9)0.0094 (10)
C310.0158 (10)0.0189 (11)0.0168 (10)0.0020 (8)−0.0005 (8)0.0023 (8)
C320.0220 (11)0.0195 (11)0.0213 (11)0.0037 (9)0.0027 (9)0.0064 (9)
C330.0222 (12)0.0267 (13)0.0226 (12)0.0060 (10)0.0058 (9)0.0044 (10)
C340.0223 (12)0.0200 (12)0.0292 (13)0.0076 (9)−0.0005 (10)0.0008 (10)
C350.0238 (12)0.0182 (12)0.0327 (13)0.0051 (9)−0.0001 (10)0.0067 (10)
C360.0192 (11)0.0207 (12)0.0249 (11)0.0015 (9)0.0021 (9)0.0097 (9)
C410.0186 (11)0.0210 (12)0.0210 (11)0.0059 (9)0.0028 (9)0.0002 (9)
C420.0209 (11)0.0246 (12)0.0260 (12)0.0033 (9)0.0032 (9)0.0056 (10)
C430.0178 (11)0.0307 (14)0.0315 (13)0.0006 (10)0.0007 (10)0.0054 (11)
C440.0204 (12)0.0305 (13)0.0325 (13)0.0090 (10)−0.0014 (10)0.0078 (11)
C450.0253 (12)0.0302 (14)0.0344 (13)0.0119 (10)0.0064 (10)0.0129 (11)
C460.0195 (11)0.0195 (12)0.0328 (13)0.0035 (9)0.0045 (10)0.0049 (10)
C510.0168 (11)0.0229 (12)0.0216 (11)0.0049 (9)−0.0040 (9)0.0041 (9)
C520.0288 (13)0.0263 (13)0.0220 (11)0.0077 (10)−0.0006 (10)0.0069 (10)
C530.0388 (15)0.0274 (14)0.0294 (13)0.0132 (11)−0.0003 (11)0.0043 (11)
C540.0286 (13)0.0426 (16)0.0242 (12)0.0169 (12)0.0005 (10)0.0021 (11)
C550.0207 (12)0.0375 (14)0.0254 (12)0.0079 (10)0.0028 (10)0.0105 (11)
C560.0194 (11)0.0254 (13)0.0301 (13)0.0048 (9)−0.0001 (10)0.0078 (10)
Geometric parameters (Å, º) top
P1—C11.817 (2)C25—H250.95
P1—C211.807 (2)C26—H260.95
P1—C311.801 (2)C31—C361.388 (3)
P2—C21.808 (2)C31—C321.397 (3)
P2—C411.809 (2)C32—C331.383 (3)
P2—C511.819 (2)C32—H320.95
P1—C171.722 (2)C33—C341.394 (3)
C17—C181.393 (3)C33—H330.95
C1—C21.532 (3)C34—C351.378 (3)
C1—H1A0.99C34—H340.95
C1—H1B0.99C35—C361.393 (3)
C2—H2A0.99C35—H350.95
C2—H2B0.99C36—H360.95
C17—H170.95C41—C461.392 (3)
C18—O181.277 (3)C41—C421.393 (3)
C18—C111.503 (3)C42—C431.395 (3)
P2—O21.415 (2)C42—H420.95
C11—C161.394 (3)C43—C441.380 (4)
C11—C121.394 (3)C43—H430.95
C12—C131.391 (3)C44—C451.385 (4)
C12—H120.95C44—H440.95
C13—C141.381 (4)C45—C461.386 (3)
C13—H130.95C45—H450.95
C14—C151.381 (4)C46—H460.95
C14—H140.95C51—C521.381 (3)
C15—C161.391 (4)C51—C561.400 (3)
C15—H150.95C52—C531.391 (4)
C16—H160.95C52—H520.95
C21—C221.389 (3)C53—C541.388 (4)
C21—C261.398 (3)C53—H530.95
C22—C231.393 (3)C54—C551.375 (4)
C22—H220.95C54—H540.95
C23—C241.393 (4)C55—C561.392 (3)
C23—H230.95C55—H550.95
C24—C251.383 (4)C56—H560.95
C24—H240.95O1—H1C0.95
C25—C261.391 (3)O1—H1D0.95
C1—P1—C17114.73 (11)C24—C25—H25120.0
C1—P1—C21105.51 (10)C26—C25—H25120.0
C1—P1—C31106.67 (10)C25—C26—C21120.0 (2)
C17—P1—C21105.46 (10)C25—C26—H26120.0
C17—P1—C31115.03 (11)C21—C26—H26120.0
C21—P1—C31108.95 (10)C36—C31—C32119.8 (2)
P1—C17—C18125.76 (18)C36—C31—P1119.43 (17)
C17—C18—O18124.6 (2)C32—C31—P1120.81 (17)
C2—P2—O2117.61 (13)C33—C32—C31120.1 (2)
C2—P2—C41104.48 (11)C33—C32—H32120.0
C2—P2—C51105.72 (11)C31—C32—H32120.0
O2—P2—C41112.58 (13)C32—C33—C34119.9 (2)
O2—P2—C51111.94 (13)C32—C33—H33120.1
C41—P2—C51103.22 (10)C34—C33—H33120.1
C11—C18—O18117.7 (2)C35—C34—C33120.2 (2)
C11—C18—C17117.6 (2)C35—C34—H34119.9
C2—C1—P1113.41 (16)C33—C34—H34119.9
C2—C1—H1A108.9C34—C35—C36120.2 (2)
P1—C1—H1A108.9C34—C35—H35119.9
C2—C1—H1B108.9C36—C35—H35119.9
P1—C1—H1B108.9C31—C36—C35119.9 (2)
H1A—C1—H1B107.7C31—C36—H36120.0
C1—C2—P2111.75 (15)C35—C36—H36120.0
C1—C2—H2A109.3C46—C41—C42119.1 (2)
P2—C2—H2A109.3C46—C41—P2123.10 (18)
C1—C2—H2B109.3C42—C41—P2117.69 (18)
P2—C2—H2B109.3C41—C42—C43120.3 (2)
H2A—C2—H2B107.9C41—C42—H42119.9
C18—C17—H17117.1C43—C42—H42119.9
P1—C17—H17117.1C44—C43—C42119.8 (2)
C16—C11—C12118.4 (2)C44—C43—H43120.1
C16—C11—C18119.0 (2)C42—C43—H43120.1
C12—C11—C18122.5 (2)C43—C44—C45120.4 (2)
C13—C12—C11120.9 (2)C43—C44—H44119.8
C13—C12—H12119.6C45—C44—H44119.8
C11—C12—H12119.6C44—C45—C46119.8 (2)
C14—C13—C12120.0 (2)C44—C45—H45120.1
C14—C13—H13120.0C46—C45—H45120.1
C12—C13—H13120.0C45—C46—C41120.6 (2)
C13—C14—C15119.9 (2)C45—C46—H46119.7
C13—C14—H14120.1C41—C46—H46119.7
C15—C14—H14120.1C52—C51—C56119.5 (2)
C14—C15—C16120.3 (2)C52—C51—P2118.25 (18)
C14—C15—H15119.9C56—C51—P2122.20 (18)
C16—C15—H15119.9C51—C52—C53120.9 (2)
C15—C16—C11120.6 (2)C51—C52—H52119.6
C15—C16—H16119.7C53—C52—H52119.6
C11—C16—H16119.7C54—C53—C52119.4 (2)
C22—C21—C26119.7 (2)C54—C53—H53120.3
C22—C21—P1122.47 (17)C52—C53—H53120.3
C26—C21—P1117.69 (17)C55—C54—C53120.1 (2)
C21—C22—C23120.0 (2)C55—C54—H54119.9
C21—C22—H22120.0C53—C54—H54119.9
C23—C22—H22120.0C54—C55—C56120.8 (2)
C22—C23—C24119.9 (2)C54—C55—H55119.6
C22—C23—H23120.0C56—C55—H55119.6
C24—C23—H23120.0C55—C56—C51119.3 (2)
C25—C24—C23120.2 (2)C55—C56—H56120.3
C25—C24—H24119.9C51—C56—H56120.3
C23—C24—H24119.9H1C—O1—H1D97.0
C24—C25—C26120.1 (2)
P1—C1—C2—P2−169.97 (12)C1—P1—C31—C36137.97 (18)
C17—P1—C1—C277.30 (18)C17—P1—C31—C32−170.64 (17)
C21—P1—C1—C2−167.09 (16)C21—P1—C31—C3271.2 (2)
C31—P1—C1—C2−51.31 (18)C1—P1—C31—C32−42.2 (2)
O2—P2—C2—C1−59.4 (2)C36—C31—C32—C330.0 (3)
C41—P2—C2—C1174.93 (16)P1—C31—C32—C33−179.79 (18)
C51—P2—C2—C166.39 (18)C31—C32—C33—C340.0 (3)
C31—P1—C17—C1865.2 (2)C32—C33—C34—C350.2 (4)
C21—P1—C17—C18−174.7 (2)C33—C34—C35—C36−0.6 (4)
C1—P1—C17—C18−59.1 (2)C32—C31—C36—C35−0.4 (3)
P1—C17—C18—O18−2.6 (4)P1—C31—C36—C35179.47 (18)
P1—C17—C18—C11175.31 (17)C34—C35—C36—C310.6 (4)
O18—C18—C11—C1634.4 (3)O2—P2—C41—C46−163.9 (2)
C17—C18—C11—C16−143.7 (2)C2—P2—C41—C46−35.1 (2)
O18—C18—C11—C12−147.2 (2)C51—P2—C41—C4675.2 (2)
C17—C18—C11—C1234.7 (3)O2—P2—C41—C4219.7 (2)
C16—C11—C12—C130.3 (3)C2—P2—C41—C42148.40 (18)
C18—C11—C12—C13−178.2 (2)C51—P2—C41—C42−101.23 (19)
C11—C12—C13—C140.5 (4)C46—C41—C42—C43−0.9 (3)
C12—C13—C14—C15−0.4 (4)P2—C41—C42—C43175.69 (18)
C13—C14—C15—C16−0.4 (4)C41—C42—C43—C440.6 (4)
C14—C15—C16—C111.2 (4)C42—C43—C44—C450.0 (4)
C12—C11—C16—C15−1.1 (4)C43—C44—C45—C46−0.3 (4)
C18—C11—C16—C15177.4 (2)C44—C45—C46—C41−0.1 (4)
C17—P1—C21—C22−114.7 (2)C42—C41—C46—C450.7 (3)
C31—P1—C21—C229.2 (2)P2—C41—C46—C45−175.73 (18)
C1—P1—C21—C22123.45 (19)O2—P2—C51—C52−13.5 (2)
C17—P1—C21—C2661.9 (2)C2—P2—C51—C52−142.77 (18)
C31—P1—C21—C26−174.12 (17)C41—P2—C51—C52107.8 (2)
C1—P1—C21—C26−59.9 (2)O2—P2—C51—C56168.8 (2)
C26—C21—C22—C23−1.1 (3)C2—P2—C51—C5639.6 (2)
P1—C21—C22—C23175.45 (17)C41—P2—C51—C56−69.8 (2)
C21—C22—C23—C241.4 (3)C56—C51—C52—C530.1 (4)
C22—C23—C24—C25−0.7 (4)P2—C51—C52—C53−177.56 (19)
C23—C24—C25—C26−0.4 (4)C51—C52—C53—C541.0 (4)
C24—C25—C26—C210.7 (4)C52—C53—C54—C55−0.8 (4)
C22—C21—C26—C250.0 (3)C53—C54—C55—C56−0.6 (4)
P1—C21—C26—C25−176.69 (17)C54—C55—C56—C511.7 (4)
C17—P1—C31—C369.5 (2)C52—C51—C56—C55−1.5 (3)
C21—P1—C31—C36−108.58 (18)P2—C51—C56—C55176.08 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O180.951.832.783 (3)175
C1—H1A···O2i0.992.183.147 (4)166
C2—H2B···O180.992.253.145 (3)150
C32—H32···O2i0.952.363.298 (4)168
C12—H12···Cg3ii0.952.873.777 (3)159
C26—H26···Cg4iii0.952.973.757 (3)141
C45—H45···Cg1iv0.952.773.589 (3)145
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z; (iii) x−1, y, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC34H30O1.68P2·H2O
Mr545.38
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)9.1392 (4), 11.8931 (3), 13.6025 (5)
α, β, γ (°)105.725 (2), 92.472 (2), 101.934 (2)
V (Å3)1384.67 (9)
Z2
Radiation typeMo Kα
µ (mm−1)0.19
Crystal size (mm)0.16 × 0.12 × 0.05
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995, 1997)
Tmin, Tmax0.955, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		21189, 6257, 4739
Rint0.137
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.143, 1.06
No. of reflections6257
No. of parameters353
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.70

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
P1—C11.817 (2)P1—C171.722 (2)
P1—C211.807 (2)C17—C181.393 (3)
P1—C311.801 (2)C18—O181.277 (3)
P2—C21.808 (2)C18—C111.503 (3)
P2—C411.809 (2)P2—O21.415 (2)
P2—C511.819 (2)
C1—P1—C17114.73 (11)C2—P2—O2117.61 (13)
C1—P1—C21105.51 (10)C2—P2—C41104.48 (11)
C1—P1—C31106.67 (10)C2—P2—C51105.72 (11)
C17—P1—C21105.46 (10)O2—P2—C41112.58 (13)
C17—P1—C31115.03 (11)O2—P2—C51111.94 (13)
C21—P1—C31108.95 (10)C41—P2—C51103.22 (10)
P1—C17—C18125.76 (18)C11—C18—O18117.7 (2)
C17—C18—O18124.6 (2)C11—C18—C17117.6 (2)
P1—C1—C2—P2−169.97 (12)C1—P1—C17—C18−59.1 (2)
C17—P1—C1—C277.30 (18)P1—C17—C18—C11175.31 (17)
C21—P1—C1—C2−167.09 (16)C17—C18—C11—C1234.7 (3)
C31—P1—C1—C2−51.31 (18)C1—P1—C21—C22123.45 (19)
O2—P2—C2—C1−59.4 (2)C1—P1—C31—C32−42.2 (2)
C41—P2—C2—C1174.93 (16)C2—P2—C41—C42148.40 (18)
C51—P2—C2—C166.39 (18)C2—P2—C51—C52−142.77 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O180.951.832.783 (3)175
C1—H1A···O2i0.992.183.147 (4)166
C32—H32···O2i0.952.363.298 (4)168
C12—H12···Cg3ii0.952.873.777 (3)159
C26—H26···Cg4iii0.952.973.757 (3)141
C45—H45···Cg1iv0.952.773.589 (3)145
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z; (iii) x−1, y, z; (iv) x+1, y, z.
 

Footnotes

‡Postal address: Department of Electrical Engineering and Physics, University of Dundee, Dundee DD1 4HN, Scotland.

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work.

References

First citationAitken, R. A., Karodia, N. & Lightfoot, P. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 333–340.  CrossRef Google Scholar
 First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–37.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBlessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
 First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
 First citationNonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOosawa, Y., Urabe, H., Saito, T. & Sasaki, Y. (1976). J. Organomet. Chem. 122, 113–121.  CrossRef CAS Web of Science Google Scholar
 First citationOtwinowski, 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.  Google Scholar
 First citationSchmidbaur, H., Jeong, J., Schier, A., Graf, W., Wilkinson, D. L., Muller, G. & Kruger, C. (1989). New J. Chem. 13, 3441–352.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2053-2296
Volume 60| Part 7| July 2004| Pages o475-o478
doi:10.1107/S0108270104012211
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