PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1231.
Published online 2008 June 7. doi:  10.1107/S1600536808016681
PMCID: PMC2961830

2-[Bis(3,5-dimethyl­phen­yl)­phosphor­yl]­propan-2-ol hemihydrate

Abstract

In the organic mol­ecule of the title compound, C19H25O2P·0.5H2O, the benzene rings are oriented at a dihedral angle of 54.04 (3)°. Intra­molecular C—H(...)O hydrogen bonds result in the formation of two five-membered planar rings, which are oriented with respect to the adjacent benzene rings at dihedral angles of 2.66 (3) and 2.79 (3)°. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds link the mol­ecules. The water oxygen atom lies on a twofold rotation axis.

Related literature

For related literature, see: Takao & Kazuhiko (1997 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1231-scheme1.jpg

Experimental

Crystal data

  • C19H25O2P·0.5H2O
  • M r = 324.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1231-efi1.jpg
  • a = 30.129 (6) Å
  • b = 6.2830 (13) Å
  • c = 20.192 (4) Å
  • β = 106.76 (3)°
  • V = 3660.1 (14) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 298 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.969, T max = 0.984
  • 6573 measured reflections
  • 3298 independent reflections
  • 1904 reflections with I > 2σ(I)
  • R int = 0.049
  • 3 standard reflections frequency: 120 min intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.205
  • S = 1.03
  • 3298 reflections
  • 206 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, Ils. DOI: 10.1107/S1600536808016681/hk2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016681/hk2469Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for its support.

supplementary crystallographic information

Comment

2-(Bis(3,5-dimethylphenyl)phosphoryl)propan-2-ol was first synthesized by the nucleophillic addition of acetone with di(3,5-dimethylphenyl)phosphine oxide at room temperature. We report herein its crystal structure.

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C10-C15) are, of course, planar, and the dihedral angle between them is A/B = 54.04 (3)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formation of two five-membered planar rings: C (C3/C4/P/O2/H3A) and D (C11/C12/P/O2/H11A). The dihedral angles between the adjacent rings are A/C = 2.66 (3)° and B/D = 2.79 (3)°. So, rings A, C and B, D are nearly coplanar. The coplanar ring systems are oriented at a dihedral angle of 54.70 (3)°.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

The title compound, (I) was synthesized by the reaction of di(3,5-dimethyl- phenyl)phosphine oxide (0.20 g, 0.70 mmol) (Takao & Kazuhiko, 1997) and acetone (25 ml). Crystals suitable for X-ray analysis were obtained by dissolving (I) in acetone and evaporating the solvent slowly at room temperature for about 7 d.

Refinement

H atoms were positioned geometrically, with O-H = 0.85 Å (for H2O) and 0.82 Å (for OH) and C-H = 0.93 and 0.96 Å for aromatic and methyl H and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,O), where x = 1.5 for OH and methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C19H25O2P·0.5H2OF000 = 1396
Mr = 324.87Dx = 1.179 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 30.129 (6) Åθ = 9–12º
b = 6.2830 (13) ŵ = 0.16 mm1
c = 20.192 (4) ÅT = 298 (2) K
β = 106.76 (3)ºNeedle, colorless
V = 3660.1 (14) Å30.20 × 0.10 × 0.10 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.049
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 1.4º
T = 298(2) Kh = −36→34
ω/2θ scansk = 0→7
Absorption correction: ψ scan(North et al., 1968)l = 0→24
Tmin = 0.969, Tmax = 0.9843 standard reflections
6573 measured reflections every 120 min
3298 independent reflections intensity decay: none
1904 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.205  w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3298 reflectionsΔρmax = 0.49 e Å3
206 parametersΔρmin = −0.55 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 > 2sigma(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*/UeqOcc. (<1)
P0.40003 (3)0.20845 (15)0.59292 (5)0.0338 (3)
OW0.50000.4938 (10)0.75000.146 (3)
HWA0.51270.54530.78990.175*0.50
O10.39553 (9)−0.2053 (4)0.58847 (14)0.0526 (8)
H1A0.4058−0.32390.60130.079*
C10.44847 (16)0.5766 (9)0.3932 (3)0.0735 (15)
H1B0.44610.56510.34490.110*
H1C0.48040.56510.41990.110*
H1D0.43640.71170.40200.110*
O20.42908 (8)0.3898 (4)0.62967 (13)0.0428 (7)
C20.42087 (13)0.3997 (7)0.4134 (2)0.0493 (10)
C30.41939 (12)0.3820 (6)0.4812 (2)0.0434 (9)
H3A0.43450.48330.51350.052*
C40.39592 (11)0.2167 (6)0.50207 (18)0.0371 (8)
C50.37267 (12)0.0663 (6)0.45310 (19)0.0425 (9)
H5A0.3567−0.04500.46640.051*
C60.37332 (13)0.0829 (7)0.3851 (2)0.0485 (11)
C70.39760 (14)0.2487 (7)0.3663 (2)0.0538 (11)
H7A0.39820.25870.32060.065*
C80.34811 (16)−0.0813 (9)0.3322 (2)0.0685 (14)
H8A0.3523−0.04810.28800.103*
H8B0.3157−0.07930.32880.103*
H8C0.3605−0.22020.34650.103*
C90.28814 (17)0.5685 (10)0.7141 (3)0.0817 (17)
H9A0.25710.56310.71780.123*
H9B0.29370.70590.69730.123*
H9C0.30970.54420.75870.123*
C100.29420 (14)0.3982 (7)0.6642 (2)0.0515 (11)
C110.33647 (13)0.3767 (6)0.65031 (19)0.0437 (9)
H11A0.36070.46850.67100.052*
C120.34291 (12)0.2187 (6)0.60557 (17)0.0350 (8)
C130.30647 (12)0.0836 (6)0.57377 (19)0.0405 (9)
H13A0.3107−0.02140.54370.049*
C140.26351 (13)0.1041 (7)0.5865 (2)0.0452 (10)
C150.25866 (14)0.2611 (7)0.6316 (2)0.0489 (10)
H15A0.23020.27550.64050.059*
C160.22411 (15)−0.0427 (8)0.5522 (3)0.0649 (13)
H16A0.2189−0.03890.50300.097*
H16B0.19650.00250.56290.097*
H16C0.2317−0.18520.56870.097*
C170.42596 (12)−0.0481 (6)0.62715 (19)0.0369 (8)
C180.42841 (16)−0.0606 (7)0.7034 (2)0.0587 (12)
H18A0.4425−0.19270.72220.088*
H18B0.3977−0.05280.70820.088*
H18C0.44660.05580.72770.088*
C190.47388 (13)−0.0667 (7)0.6165 (2)0.0540 (11)
H19A0.4874−0.20090.63430.081*
H19B0.49320.04690.64060.081*
H19C0.4712−0.05770.56810.081*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P0.0353 (5)0.0217 (5)0.0407 (5)−0.0001 (4)0.0049 (4)0.0001 (4)
OW0.183 (7)0.085 (5)0.102 (5)0.000−0.065 (5)0.000
O10.0576 (17)0.0242 (13)0.0655 (18)−0.0009 (13)0.0012 (14)0.0037 (13)
C10.065 (3)0.073 (3)0.094 (4)0.003 (3)0.041 (3)0.018 (3)
O20.0418 (14)0.0225 (13)0.0552 (17)−0.0023 (12)−0.0003 (12)−0.0026 (12)
C20.042 (2)0.049 (3)0.061 (3)0.009 (2)0.023 (2)0.012 (2)
C30.042 (2)0.036 (2)0.051 (2)0.0029 (18)0.0110 (18)0.0028 (19)
C40.0331 (18)0.0357 (19)0.041 (2)0.0043 (17)0.0092 (15)0.0052 (17)
C50.038 (2)0.044 (2)0.045 (2)−0.0040 (18)0.0094 (17)0.0009 (19)
C60.042 (2)0.060 (3)0.042 (2)0.006 (2)0.0092 (18)−0.008 (2)
C70.052 (2)0.068 (3)0.045 (2)0.013 (2)0.0178 (19)0.010 (2)
C80.070 (3)0.081 (4)0.048 (3)0.003 (3)0.007 (2)−0.020 (3)
C90.070 (3)0.091 (4)0.086 (4)0.008 (3)0.026 (3)−0.044 (3)
C100.049 (2)0.049 (3)0.055 (3)0.005 (2)0.012 (2)−0.010 (2)
C110.042 (2)0.040 (2)0.044 (2)−0.0018 (19)0.0036 (17)−0.0072 (19)
C120.044 (2)0.0252 (17)0.0344 (18)0.0025 (16)0.0082 (15)0.0033 (16)
C130.045 (2)0.028 (2)0.045 (2)−0.0007 (17)0.0090 (17)−0.0051 (17)
C140.039 (2)0.044 (2)0.052 (2)−0.0008 (19)0.0119 (18)0.002 (2)
C150.043 (2)0.049 (3)0.055 (2)0.007 (2)0.0163 (19)0.002 (2)
C160.044 (2)0.066 (3)0.082 (3)−0.012 (2)0.013 (2)−0.007 (3)
C170.0374 (19)0.0245 (17)0.046 (2)0.0037 (16)0.0073 (16)0.0044 (16)
C180.076 (3)0.045 (3)0.053 (3)0.011 (2)0.016 (2)0.011 (2)
C190.042 (2)0.046 (2)0.072 (3)0.010 (2)0.014 (2)0.009 (2)

Geometric parameters (Å, °)

P—O21.497 (2)C9—H9A0.9600
P—C41.803 (4)C9—H9B0.9600
P—C121.812 (4)C9—H9C0.9600
P—C171.837 (4)C10—C151.384 (6)
OW—HWA0.8500C10—C111.387 (5)
O1—C171.419 (4)C11—C121.393 (5)
O1—H1A0.8200C11—H11A0.9300
C1—C21.513 (6)C12—C131.390 (5)
C1—H1B0.9600C13—C141.397 (5)
C1—H1C0.9600C13—H13A0.9300
C1—H1D0.9600C14—C151.378 (6)
C2—C71.383 (6)C14—C161.505 (6)
C2—C31.388 (5)C15—H15A0.9300
C3—C41.389 (5)C16—H16A0.9600
C3—H3A0.9300C16—H16B0.9600
C4—C51.400 (5)C16—H16C0.9600
C5—C61.383 (5)C17—C181.521 (5)
C5—H5A0.9300C17—C191.524 (5)
C6—C71.388 (6)C18—H18A0.9600
C6—C81.521 (6)C18—H18B0.9600
C7—H7A0.9300C18—H18C0.9600
C8—H8A0.9600C19—H19A0.9600
C8—H8B0.9600C19—H19B0.9600
C8—H8C0.9600C19—H19C0.9600
C9—C101.516 (6)
O2—P—C4109.95 (17)C15—C10—C11118.2 (4)
O2—P—C12110.28 (16)C15—C10—C9122.0 (4)
C4—P—C12110.66 (16)C11—C10—C9119.8 (4)
O2—P—C17110.91 (15)C10—C11—C12120.5 (4)
C4—P—C17107.75 (18)C10—C11—H11A119.7
C12—P—C17107.23 (17)C12—C11—H11A119.7
C17—O1—H1A109.5C13—C12—C11119.7 (3)
C2—C1—H1B109.5C13—C12—P124.7 (3)
C2—C1—H1C109.5C11—C12—P115.6 (3)
H1B—C1—H1C109.5C12—C13—C14120.6 (3)
C2—C1—H1D109.5C12—C13—H13A119.7
H1B—C1—H1D109.5C14—C13—H13A119.7
H1C—C1—H1D109.5C15—C14—C13117.9 (4)
C7—C2—C3118.0 (4)C15—C14—C16121.5 (4)
C7—C2—C1121.8 (4)C13—C14—C16120.5 (4)
C3—C2—C1120.1 (4)C14—C15—C10123.0 (4)
C2—C3—C4121.5 (4)C14—C15—H15A118.5
C2—C3—H3A119.2C10—C15—H15A118.5
C4—C3—H3A119.2C14—C16—H16A109.5
C3—C4—C5119.0 (4)C14—C16—H16B109.5
C3—C4—P116.0 (3)H16A—C16—H16B109.5
C5—C4—P124.9 (3)C14—C16—H16C109.5
C6—C5—C4120.2 (4)H16A—C16—H16C109.5
C6—C5—H5A119.9H16B—C16—H16C109.5
C4—C5—H5A119.9O1—C17—C18110.9 (3)
C5—C6—C7119.2 (4)O1—C17—C19110.9 (3)
C5—C6—C8119.9 (4)C18—C17—C19111.5 (3)
C7—C6—C8120.9 (4)O1—C17—P105.5 (2)
C2—C7—C6122.0 (4)C18—C17—P108.5 (3)
C2—C7—H7A119.0C19—C17—P109.4 (3)
C6—C7—H7A119.0C17—C18—H18A109.5
C6—C8—H8A109.5C17—C18—H18B109.5
C6—C8—H8B109.5H18A—C18—H18B109.5
H8A—C8—H8B109.5C17—C18—H18C109.5
C6—C8—H8C109.5H18A—C18—H18C109.5
H8A—C8—H8C109.5H18B—C18—H18C109.5
H8B—C8—H8C109.5C17—C19—H19A109.5
C10—C9—H9A109.5C17—C19—H19B109.5
C10—C9—H9B109.5H19A—C19—H19B109.5
H9A—C9—H9B109.5C17—C19—H19C109.5
C10—C9—H9C109.5H19A—C19—H19C109.5
H9A—C9—H9C109.5H19B—C19—H19C109.5
H9B—C9—H9C109.5
C7—C2—C3—C40.9 (6)C4—P—C12—C1352.7 (4)
C1—C2—C3—C4−177.4 (4)C17—P—C12—C13−64.6 (3)
C2—C3—C4—C5−1.0 (5)O2—P—C12—C11−4.9 (3)
C2—C3—C4—P176.7 (3)C4—P—C12—C11−126.8 (3)
O2—P—C4—C30.2 (3)C17—P—C12—C11116.0 (3)
C12—P—C4—C3122.3 (3)C11—C12—C13—C14−0.3 (5)
C17—P—C4—C3−120.8 (3)P—C12—C13—C14−179.8 (3)
O2—P—C4—C5177.7 (3)C12—C13—C14—C15−0.3 (6)
C12—P—C4—C5−60.3 (4)C12—C13—C14—C16−179.9 (4)
C17—P—C4—C556.7 (3)C13—C14—C15—C100.2 (6)
C3—C4—C5—C60.2 (5)C16—C14—C15—C10179.8 (4)
P—C4—C5—C6−177.2 (3)C11—C10—C15—C140.4 (7)
C4—C5—C6—C70.6 (6)C9—C10—C15—C14−179.5 (4)
C4—C5—C6—C8179.8 (4)O2—P—C17—O1−179.9 (2)
C3—C2—C7—C6−0.1 (6)C4—P—C17—O1−59.6 (3)
C1—C2—C7—C6178.2 (4)C12—P—C17—O159.6 (3)
C5—C6—C7—C2−0.7 (6)O2—P—C17—C1861.2 (3)
C8—C6—C7—C2−179.9 (4)C4—P—C17—C18−178.4 (3)
C15—C10—C11—C12−1.0 (6)C12—P—C17—C18−59.2 (3)
C9—C10—C11—C12178.8 (4)O2—P—C17—C19−60.6 (3)
C10—C11—C12—C131.0 (6)C4—P—C17—C1959.8 (3)
C10—C11—C12—P−179.5 (3)C12—P—C17—C19178.9 (3)
O2—P—C12—C13174.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
OW—HWA···O2i0.852.242.811 (3)124
O1—H1A···O2ii0.821.962.775 (4)178
C3—H3A···O20.932.472.928 (5)110
C11—H11A···O20.932.492.939 (5)110

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2469).

References

  • 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.
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Takao, S. & Kazuhiko, M. (1997). EP Patent No. 0 755 937.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography