Racemic benzyl­phenyl­phosphine oxide

All interatomic distances in the title compound, C₁₃H₁₃OP, can be considered normal. The crystal was twinned with a 71:29 participation of the two polar components. The phospho­rus tetrahedron exhibits its usual deformation. The mid-part containing C_(phenyl)—P—C—C_(phenyl) is almost planar. The P=O bond makes angles of 22.2 (3) and 18.2 (2)° with the phenyl rings; the phenyl rings are inclined to each other at 4.9 (2)°. Two weak C—H...O intermolecular hydrogen bonds are found in the structure. In this way, a two-dimensional hydrogen-bond net parallel to the bc plane is created. The possibility of π-electron stacking was rejected because the neighbouring benzene rings in the crystal lattice are inclined to each other at 52.4 (2) and 61.2 (2)°. The geometrical parameters are compared to those reported in the literature for the solid-state structures of phosphine-substituted benzyl­phenyl­phosphine oxides.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.163
• Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFI_020  Alert A _refine_ls_extinction_coef is missing
          Extinction coefficient applied in corrections.


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       P(1)   -   H(1P)             ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           74.93
         From the CIF: _reflns_number_total               2329
         Count of symmetry unique reflns         1169
         Completeness (_total/calc)            199.23%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1160
         Fraction of Friedel pairs measured     0.992
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

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).

benzylphenylphosphine oxide

Crystal data

C13H13OP	F(000) = 228
Mr = 216.20	Dx = 1.264 Mg m^−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54178 Å
a = 12.817 (2) Å	Cell parameters from 25 reflections
b = 5.713 (1) Å	θ = 20.4–28.8°
c = 8.074 (3) Å	µ = 1.89 mm^−1
β = 106.15 (3)°	T = 293 K
V = 567.9 (2) Å^3	Prism, colourless
Z = 2	0.76 × 0.56 × 0.28 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2304 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 74.9°, θmin = 3.6°
ω–2θ scans	h = −16→16
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	k = 0→7
Tmin = 0.314, Tmax = 0.629	l = −10→10
2329 measured reflections	3 standard reflections every 60 min
2329 independent reflections	intensity decay: 0.2%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + (0.1386P)^2 + 0.0859P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.163	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.22 e Å^−3
2329 reflections	Δρmin = −0.39 e Å^−3
138 parameters	Extinction correction: SHELXL97
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)
Secondary atom site location: structure-invariant direct methods

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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.90551 (6)	0.63168 (11)	0.50064 (8)	0.0484 (2)
H1P	0.8828 (7)	0.6900 (17)	0.651 (4)	0.058*
O1	0.8845 (2)	0.3776 (4)	0.4741 (4)	0.0651 (8)
C1	0.8248 (3)	0.8193 (5)	0.3352 (4)	0.0505 (6)
H1A	0.8453	0.9810	0.3632	0.061*
H1B	0.8389	0.7827	0.2261	0.061*
C2	0.7051 (2)	0.7889 (5)	0.3181 (3)	0.0474 (6)
C3	0.6514 (3)	0.9540 (7)	0.3904 (4)	0.0599 (7)
H3	0.6889	1.0843	0.4459	0.072*
C4	0.5431 (4)	0.9262 (9)	0.3806 (6)	0.0719 (9)
H4	0.5080	1.0377	0.4298	0.086*
C5	0.4861 (3)	0.7343 (9)	0.2983 (5)	0.0715 (9)
H5	0.4132	0.7157	0.2927	0.086*
C6	0.5388 (3)	0.5697 (8)	0.2243 (6)	0.0700 (9)
H6	0.5010	0.4407	0.1675	0.084*
C7	0.6475 (3)	0.5975 (6)	0.2350 (5)	0.0598 (8)
H7	0.6825	0.4861	0.1856	0.072*
C8	1.0452 (2)	0.7064 (5)	0.5261 (3)	0.0490 (6)
C9	1.1110 (3)	0.5478 (6)	0.4727 (5)	0.0613 (7)
H9	1.0822	0.4074	0.4215	0.074*
C10	1.2205 (4)	0.5993 (8)	0.4957 (7)	0.0756 (11)
H10	1.2646	0.4939	0.4589	0.091*
C11	1.2635 (3)	0.8065 (9)	0.5731 (6)	0.0750 (10)
H11	1.3367	0.8398	0.5896	0.090*
C12	1.1980 (4)	0.9637 (9)	0.6260 (6)	0.0767 (11)
H12	1.2270	1.1038	0.6774	0.092*
C13	1.0899 (3)	0.9144 (7)	0.6032 (6)	0.0651 (8)
H13	1.0463	1.0213	0.6397	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0519 (4)	0.0485 (4)	0.0473 (3)	−0.0019 (3)	0.0178 (3)	0.0010 (3)
O1	0.0669 (19)	0.0512 (12)	0.079 (2)	−0.0078 (9)	0.0227 (15)	0.0054 (10)
C1	0.0517 (14)	0.0493 (13)	0.0518 (14)	0.0022 (11)	0.0167 (11)	0.0065 (12)
C2	0.0500 (14)	0.0489 (13)	0.0447 (12)	0.0017 (11)	0.0154 (10)	0.0011 (11)
C3	0.0639 (17)	0.0569 (16)	0.0590 (17)	0.0056 (15)	0.0174 (14)	−0.0085 (14)
C4	0.066 (2)	0.083 (2)	0.070 (2)	0.016 (2)	0.0246 (17)	−0.002 (2)
C5	0.0451 (15)	0.093 (3)	0.077 (2)	0.0030 (15)	0.0179 (15)	0.011 (2)
C6	0.0582 (18)	0.0709 (19)	0.077 (2)	−0.0108 (17)	0.0124 (16)	−0.0049 (18)
C7	0.0575 (18)	0.0554 (17)	0.067 (2)	−0.0025 (12)	0.0184 (14)	−0.0098 (13)
C8	0.0511 (13)	0.0498 (14)	0.0454 (12)	0.0007 (11)	0.0125 (10)	0.0013 (11)
C9	0.0633 (18)	0.0568 (16)	0.0652 (18)	0.0029 (14)	0.0198 (15)	−0.0059 (15)
C10	0.063 (2)	0.077 (2)	0.091 (3)	0.0130 (17)	0.030 (2)	0.0010 (19)
C11	0.0486 (17)	0.086 (2)	0.088 (3)	−0.0031 (18)	0.0161 (16)	0.005 (2)
C12	0.061 (2)	0.076 (2)	0.090 (3)	−0.0142 (18)	0.0168 (19)	−0.014 (2)
C13	0.063 (2)	0.0590 (17)	0.074 (2)	−0.0086 (15)	0.0204 (17)	−0.0126 (16)

Geometric parameters (Å, º)

P1—O1	1.481 (2)	C6—C7	1.381 (5)
P1—C8	1.796 (3)	C6—H6	0.9300
P1—C1	1.798 (3)	C7—H7	0.9300
P1—H1P	1.3625	C8—C9	1.386 (5)
C1—C2	1.512 (4)	C8—C13	1.389 (5)
C1—H1A	0.9700	C9—C10	1.395 (6)
C1—H1B	0.9700	C9—H9	0.9300
C2—C7	1.384 (4)	C10—C11	1.379 (7)
C2—C3	1.388 (5)	C10—H10	0.9300
C3—C4	1.378 (6)	C11—C12	1.376 (7)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.380 (6)	C12—C13	1.375 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.387 (6)	C13—H13	0.9300
C5—H5	0.9300
O1—P1—C8	112.62 (15)	C7—C6—C5	119.9 (4)
O1—P1—C1	115.66 (16)	C7—C6—H6	120.0
C8—P1—C1	107.02 (14)	C5—C6—H6	120.0
O1—P1—H1P	107.0	C6—C7—C2	120.9 (3)
C8—P1—H1P	107.0	C6—C7—H7	119.5
C1—P1—H1P	107.0	C2—C7—H7	119.5
C2—C1—P1	111.0 (2)	C9—C8—C13	119.2 (3)
C2—C1—H1A	109.4	C9—C8—P1	118.8 (2)
P1—C1—H1A	109.4	C13—C8—P1	121.9 (3)
C2—C1—H1B	109.4	C8—C9—C10	119.8 (3)
P1—C1—H1B	109.4	C8—C9—H9	120.1
H1A—C1—H1B	108.0	C10—C9—H9	120.1
C7—C2—C3	118.8 (3)	C11—C10—C9	120.1 (4)
C7—C2—C1	121.7 (3)	C11—C10—H10	119.9
C3—C2—C1	119.5 (3)	C9—C10—H10	119.9
C4—C3—C2	120.4 (4)	C12—C11—C10	120.0 (4)
C4—C3—H3	119.8	C12—C11—H11	120.0
C2—C3—H3	119.8	C10—C11—H11	120.0
C3—C4—C5	120.6 (4)	C13—C12—C11	120.2 (4)
C3—C4—H4	119.7	C13—C12—H12	119.9
C5—C4—H4	119.7	C11—C12—H12	119.9
C4—C5—C6	119.4 (3)	C12—C13—C8	120.7 (4)
C4—C5—H5	120.3	C12—C13—H13	119.7
C6—C5—H5	120.3	C8—C13—H13	119.7
C9—C8—P1—O1	17.8 (3)	C8—P1—C1—C2	−173.6 (2)
C13—C8—P1—O1	−159.9 (3)	P1—C1—C2—C3	101.8 (3)
C9—C8—P1—C1	−110.3 (3)	P1—C1—C2—C7	−76.9 (3)
C13—C8—P1—C1	71.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1^i	0.97	2.44	3.397 (4)	170
C1—H1B···O1^ii	0.97	2.45	3.405 (5)	170

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