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All interatomic distances in the title compound, C13H13O2P, can be considered normal. The phospho­rus tetrahedron exhibits its usual deformation. The (2-methoxy­phenyl)­phosphine section is almost planar. The structure is assembled via intermolecular C—H...O hydrogen bonds, to form of one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002143/bt6101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002143/bt6101Isup2.hkl
Contains datablock I

CCDC reference: 182599

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.122
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor P(1) - H(1P) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Secondary phosphine oxides are important synthetic intermediates in organophosphorus chemistry and their high reactivity is typically connected with the presence of a relatively acidic hydrogen in their structure (Engel, 1988). They exist in two tautomeric forms: R2P(O)H and R2POH, the former being predominant in the equilibrium (Bailey & Fox, 1963, 1964). There are, however, cases like in the transition metal complexes, where the latter form is seen exclusively (Parkins, 1996; Han et al., 1996). It was therefore deemed interesting to study the crystal structure of some model secondary phosphine oxides in order to reveal their tautomeric preferences in the solid state and to study the character of the expected hydrogen bonding implied by their acidic functionality. The selected models include one alkylarylphosphine oxide, i.e. benzylphenylphosphine oxide (Kruszynski et al., 2002), and one diarylphosphine oxide, i.e. (2-methoxyphenyl)phenylphosphine oxide, (I).

The perspective view of (I), together with the atom-numbering scheme, is shown in Fig. 1. A l l interatomic distances can be considered as normal and the phenyl rings are planar in the range of experimental error. The overall molecular geometry of (I) is similar to the (2-methoxyphenyl)(phenyl)vinylphosphine oxide, (II) (Wieczorek, 1995). The weighted r.m.s. deviation for all non-H atoms in (I) and respective atoms of (II) is 0.156 (4) Å. The superposition of the two molecules (I) and (II) is shown in Fig. 2. The phosphorous tetrahedron exhibits its usual deformation, with C—P—C and C—P—H angles smaller than tetrahedral and O—P—C and O—P—H angles greater than tetrahedral (Table 1). The PO bond makes the angles of 7.6 (2) and 46.56 (2)° with phenyl rings indicated by C1 and C8 atoms, respectively. Analogous angles in (II) are 1.7 (1) and 52.0 (1)°. The (2-methoxyphenyl)phosphine part is almost planar with maximum deviation of 0.0181 (17) Å for C6 atom. The adjacent C atom deviates by -1.551 (2) Å from the above plane and the O atom deviates by 0.190 (2) Å. The dihedral angle between weighted least-squares planes of the phenyl rings is 82.53 (7)°. In the structure can be found one C—H···O short intermolecular interaction (Table 2), which can be considered as a weak intermolecular hydrogen bond (Taylor & Kennard, 1982; Desiraju & Steiner, 1999). In this way, the one-dimensional hydrogen-bond chain is created (Fig. 3). There are no unusual intermolecular short contacts except for the hydrogen bond described in Table 2.

Experimental top

The title compound was synthesized according to previously published procedures and its physical and spectral properties were in full agreement with the literature data (Maffei & Buono, 1988; Emmick & Letsinger, 1968). Crystals were obtained by crystallization from benzene.

Refinement top

All H atoms, except that bonded to the P atom, were set in calculated positions and treated as riding on the adjacent C atom. The H atom bonded to the P atom was located in a difference Fourier syntheses and refined isotropically. The methyl group was allowed to rotate about its local threefold axis.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Superposition of molecules (I) and (II). Molecule (II) is indicated by dashed lines.
[Figure 3] Fig. 3. Part of the molecular packing of the title compound showing the intermolecular hydrogen bonds creating a chain structure along the x axis. Hydrogen bonds are indicated by dashed lines.
(2-methoxyphenyl)phenylphosphine oxide top
Crystal data top
C13H13O2PF(000) = 488
Mr = 232.20Dx = 1.287 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.576 (3) ÅCell parameters from 99 reflections
b = 8.804 (4) Åθ = 18.7–28.9°
c = 15.921 (6) ŵ = 1.89 mm1
β = 94.69 (3)°T = 293 K
V = 1198.1 (8) Å3Prism, colourless
Z = 40.55 × 0.23 × 0.12 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2175 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 75.1°, θmin = 5.2°
ω–2θ scansh = 010
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
k = 1111
Tmin = 0.421, Tmax = 0.809l = 1919
5076 measured reflections3 standard reflections every 60 min
2465 independent reflections intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0533P)2 + 0.2516P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2465 reflectionsΔρmax = 0.18 e Å3
151 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0052 (7)
Crystal data top
C13H13O2PV = 1198.1 (8) Å3
Mr = 232.20Z = 4
Monoclinic, P21/cCu Kα radiation
a = 8.576 (3) ŵ = 1.89 mm1
b = 8.804 (4) ÅT = 293 K
c = 15.921 (6) Å0.55 × 0.23 × 0.12 mm
β = 94.69 (3)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
2175 reflections with I > 2σ(I)
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
Rint = 0.029
Tmin = 0.421, Tmax = 0.8093 standard reflections every 60 min
5076 measured reflections intensity decay: 0.5%
2465 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.18 e Å3
2465 reflectionsΔρmin = 0.22 e Å3
151 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*/Ueq
P10.28987 (5)0.21983 (6)0.35898 (3)0.0632 (2)
O10.38235 (17)0.08178 (19)0.34478 (11)0.0935 (5)
O20.18333 (16)0.50916 (15)0.42498 (8)0.0696 (4)
C10.33299 (18)0.29594 (19)0.46244 (12)0.0572 (4)
C20.27410 (19)0.4357 (2)0.48634 (11)0.0573 (4)
C30.3075 (2)0.4893 (3)0.56705 (13)0.0759 (5)
H30.26930.58310.58270.091*
C40.3976 (3)0.4032 (3)0.62427 (14)0.0903 (7)
H40.41890.43920.67890.108*
C50.4566 (3)0.2661 (3)0.60271 (17)0.0926 (8)
H50.51710.20910.64230.111*
C60.4255 (2)0.2130 (2)0.52162 (16)0.0780 (6)
H60.46690.12030.50640.094*
C70.1220 (3)0.6544 (2)0.44369 (17)0.0866 (7)
H7A0.06280.64670.49220.130*
H7B0.05530.68970.39640.130*
H7C0.20660.72480.45520.130*
C80.0832 (2)0.1890 (2)0.34440 (10)0.0573 (4)
C90.0199 (2)0.0681 (2)0.38569 (14)0.0739 (5)
H90.08390.00600.42100.089*
C100.1394 (3)0.0404 (3)0.37403 (18)0.0980 (8)
H100.18270.04020.40190.118*
C110.2339 (2)0.1313 (4)0.32146 (18)0.1032 (10)
H110.34060.11160.31320.124*
C120.1710 (3)0.2499 (4)0.28154 (17)0.1017 (9)
H120.23540.31140.24610.122*
C130.0137 (3)0.2803 (3)0.29269 (13)0.0798 (6)
H130.02760.36260.26540.096*
H1P0.3174 (19)0.337 (2)0.3094 (11)0.058 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0478 (3)0.0675 (3)0.0758 (3)0.00054 (18)0.0147 (2)0.0080 (2)
O10.0636 (8)0.0927 (11)0.1257 (13)0.0169 (8)0.0169 (8)0.0313 (10)
O20.0737 (8)0.0592 (7)0.0751 (8)0.0126 (6)0.0005 (6)0.0024 (6)
C10.0413 (7)0.0557 (9)0.0747 (10)0.0054 (6)0.0043 (7)0.0045 (8)
C20.0504 (8)0.0576 (9)0.0640 (9)0.0069 (7)0.0062 (7)0.0039 (7)
C30.0784 (13)0.0769 (13)0.0727 (12)0.0154 (10)0.0082 (10)0.0083 (10)
C40.0888 (15)0.1101 (19)0.0693 (12)0.0360 (14)0.0096 (11)0.0076 (12)
C50.0736 (13)0.0992 (17)0.0992 (16)0.0261 (13)0.0284 (12)0.0327 (14)
C60.0547 (10)0.0638 (11)0.1126 (16)0.0054 (8)0.0112 (10)0.0146 (11)
C70.0813 (14)0.0626 (12)0.1175 (18)0.0157 (10)0.0180 (13)0.0039 (12)
C80.0527 (8)0.0621 (9)0.0578 (9)0.0003 (7)0.0085 (7)0.0116 (7)
C90.0669 (11)0.0677 (11)0.0877 (13)0.0092 (9)0.0098 (9)0.0076 (10)
C100.0767 (14)0.1059 (18)0.1151 (18)0.0376 (14)0.0296 (14)0.0350 (16)
C110.0481 (10)0.155 (3)0.1065 (18)0.0113 (14)0.0077 (11)0.0657 (19)
C120.0623 (13)0.152 (3)0.0872 (15)0.0205 (15)0.0138 (12)0.0243 (16)
C130.0677 (12)0.1017 (17)0.0689 (11)0.0064 (11)0.0007 (9)0.0043 (11)
Geometric parameters (Å, º) top
P1—O11.4787 (16)C6—H60.9300
P1—C11.789 (2)C7—H7A0.9600
P1—C81.7895 (18)C7—H7B0.9600
P1—H1P1.330 (18)C7—H7C0.9600
O2—C21.362 (2)C8—C131.380 (3)
O2—C71.424 (2)C8—C91.385 (3)
C1—C61.388 (3)C9—C101.386 (3)
C1—C21.394 (2)C9—H90.9300
C2—C31.377 (3)C10—C111.373 (4)
C3—C41.374 (3)C10—H100.9300
C3—H30.9300C11—C121.357 (4)
C4—C51.363 (4)C11—H110.9300
C4—H40.9300C12—C131.373 (3)
C5—C61.379 (4)C12—H120.9300
C5—H50.9300C13—H130.9300
O1—P1—C1112.06 (9)O2—C7—H7A109.5
O1—P1—C8113.17 (9)O2—C7—H7B109.5
C1—P1—C8107.72 (8)H7A—C7—H7B109.5
O1—P1—H1P115.0 (7)O2—C7—H7C109.5
C1—P1—H1P102.9 (8)H7A—C7—H7C109.5
C8—P1—H1P105.2 (7)H7B—C7—H7C109.5
C2—O2—C7118.42 (16)C13—C8—C9119.43 (18)
C6—C1—C2118.58 (18)C13—C8—P1122.06 (16)
C6—C1—P1119.43 (16)C9—C8—P1118.51 (15)
C2—C1—P1121.97 (13)C8—C9—C10119.5 (2)
O2—C2—C3124.72 (18)C8—C9—H9120.3
O2—C2—C1114.95 (15)C10—C9—H9120.3
C3—C2—C1120.33 (18)C11—C10—C9120.3 (3)
C4—C3—C2119.5 (2)C11—C10—H10119.8
C4—C3—H3120.3C9—C10—H10119.8
C2—C3—H3120.3C12—C11—C10119.8 (2)
C5—C4—C3121.5 (2)C12—C11—H11120.1
C5—C4—H4119.3C10—C11—H11120.1
C3—C4—H4119.3C11—C12—C13120.9 (3)
C4—C5—C6119.3 (2)C11—C12—H12119.5
C4—C5—H5120.4C13—C12—H12119.5
C6—C5—H5120.4C12—C13—C8120.1 (2)
C5—C6—C1120.9 (2)C12—C13—H13120.0
C5—C6—H6119.6C8—C13—H13120.0
C1—C6—H6119.6
C3—C2—O2—C72.3 (3)C1—C2—O2—C7178.40 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.483.371 (3)160
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC13H13O2P
Mr232.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.576 (3), 8.804 (4), 15.921 (6)
β (°) 94.69 (3)
V3)1198.1 (8)
Z4
Radiation typeCu Kα
µ (mm1)1.89
Crystal size (mm)0.55 × 0.23 × 0.12
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionNumerical
(X-RED; Stoe & Cie, 1999)
Tmin, Tmax0.421, 0.809
No. of measured, independent and
observed [I > 2σ(I)] reflections
5076, 2465, 2175
Rint0.029
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.122, 1.09
No. of reflections2465
No. of parameters151
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.22

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990a), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
P1—O11.4787 (16)P1—C81.7895 (18)
P1—C11.789 (2)P1—H1P1.330 (18)
O1—P1—C1112.06 (9)O1—P1—H1P115.0 (7)
O1—P1—C8113.17 (9)C1—P1—H1P102.9 (8)
C1—P1—C8107.72 (8)C8—P1—H1P105.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O1i0.932.483.371 (3)159.8
Symmetry code: (i) x1, y, z.
 

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