All interatomic distances in the title compound, C
13H
13OP, 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.
Supporting information
CCDC reference: 183787
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Prism, colourless |
Z = 2 | 0.76 × 0.56 × 0.28 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.1386P)2 + 0.0859P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O1i | 0.97 | 2.44 | 3.397 (4) | 170 |
C1—H1B···O1ii | 0.97 | 2.45 | 3.405 (5) | 170 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z−1/2. |