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The title compound, C21H17OP, is a rare example of a structurally characterized allenyl phosphine oxide. The allenyl moiety is linear, as expected, with a bond angle of 179.2 (3)° at the central C atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027710/dn6171sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027710/dn6171Isup2.hkl
Contains datablock I

CCDC reference: 259109

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.175
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
C21H17OPF(000) = 664.00
Mr = 316.34Dx = 1.252 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 9907 reflections
a = 9.5560 (3) Åθ = 1.3–27.3°
b = 15.4559 (5) ŵ = 0.17 mm1
c = 12.0143 (3) ÅT = 296 K
β = 108.904 (2)°Block, colorless
V = 1678.76 (9) Å30.57 × 0.25 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2484 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.038
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1212
Tmin = 0.820, Tmax = 0.975k = 1820
15140 measured reflectionsl = 1415
3751 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[0.0059Fo2 + σ(Fo2)]/(4Fo2)
wR(F2) = 0.175(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.30 e Å3
2484 reflectionsΔρmin = 0.34 e Å3
208 parameters
Special details top

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.43434 (8)0.25859 (5)0.43802 (5)0.0362 (2)
O10.4443 (3)0.2791 (1)0.3202 (2)0.0516 (6)
C10.2871 (4)0.3994 (2)0.6313 (3)0.0546 (9)
C20.3866 (3)0.3736 (2)0.5875 (2)0.0410 (7)
C30.4868 (3)0.3472 (2)0.5414 (2)0.0366 (7)
C40.6348 (3)0.3893 (2)0.5700 (2)0.0400 (7)
C50.6692 (4)0.4597 (2)0.6452 (3)0.0549 (9)
C60.8071 (5)0.4987 (3)0.6730 (3)0.069 (1)
C70.9106 (4)0.4683 (3)0.6257 (3)0.066 (1)
C80.8784 (4)0.3989 (3)0.5513 (3)0.063 (1)
C90.7408 (4)0.3602 (2)0.5221 (3)0.0498 (9)
C100.5521 (3)0.1697 (2)0.5070 (2)0.0371 (7)
C110.5975 (3)0.1131 (2)0.4360 (3)0.0472 (8)
C120.6872 (4)0.0434 (2)0.4850 (3)0.058 (1)
C130.7329 (4)0.0301 (2)0.6038 (3)0.060 (1)
C140.6873 (4)0.0857 (2)0.6753 (3)0.061 (1)
C150.5979 (4)0.1555 (2)0.6280 (2)0.0474 (8)
C160.2479 (3)0.2300 (2)0.4293 (2)0.0406 (7)
C170.1368 (4)0.2502 (2)0.3253 (3)0.057 (1)
C180.0081 (4)0.2302 (3)0.3118 (4)0.075 (1)
C190.0424 (4)0.1892 (3)0.4005 (4)0.076 (1)
C200.0659 (4)0.1685 (3)0.5044 (4)0.069 (1)
C210.2108 (4)0.1891 (2)0.5188 (3)0.0530 (9)
H10.21840.44540.59170.066*
H20.29040.37540.70570.066*
H180.08580.24540.23970.085*
H60.83060.54780.72610.080*
H71.00660.49600.64490.077*
H140.71920.07590.75960.072*
H90.71800.31190.46750.060*
H80.95220.37670.51920.076*
H110.56630.12220.35160.058*
H120.71840.00400.43470.071*
H130.79660.01860.63770.071*
H150.56720.19450.67900.057*
H170.16110.27830.26180.065*
H50.59690.48180.67900.066*
H190.14460.17460.39000.092*
H200.03990.13950.56660.086*
H210.28700.17510.59240.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0359 (4)0.0406 (4)0.0320 (4)0.0009 (3)0.0110 (3)0.0006 (3)
O10.056 (1)0.066 (1)0.034 (1)0.002 (1)0.0170 (9)0.0052 (9)
C10.050 (2)0.059 (2)0.055 (2)0.007 (1)0.018 (2)0.008 (1)
C20.043 (2)0.036 (1)0.041 (1)0.002 (1)0.009 (1)0.001 (1)
C30.039 (2)0.035 (1)0.035 (1)0.001 (1)0.010 (1)0.003 (1)
C40.040 (2)0.036 (1)0.039 (1)0.002 (1)0.007 (1)0.006 (1)
C50.061 (2)0.050 (2)0.055 (2)0.012 (2)0.020 (2)0.006 (1)
C60.076 (3)0.060 (2)0.065 (2)0.027 (2)0.013 (2)0.009 (2)
C70.048 (2)0.073 (2)0.072 (2)0.021 (2)0.011 (2)0.008 (2)
C80.046 (2)0.068 (2)0.076 (2)0.009 (2)0.019 (2)0.007 (2)
C90.042 (2)0.049 (2)0.058 (2)0.005 (1)0.015 (1)0.001 (1)
C100.033 (2)0.039 (1)0.041 (1)0.002 (1)0.013 (1)0.003 (1)
C110.047 (2)0.050 (2)0.047 (2)0.002 (1)0.019 (1)0.007 (1)
C120.061 (2)0.049 (2)0.069 (2)0.012 (2)0.028 (2)0.007 (1)
C130.059 (2)0.047 (2)0.072 (2)0.013 (2)0.018 (2)0.006 (1)
C140.075 (3)0.056 (2)0.049 (2)0.012 (2)0.015 (2)0.009 (1)
C150.055 (2)0.048 (2)0.040 (1)0.006 (1)0.017 (1)0.001 (1)
C160.039 (2)0.040 (1)0.042 (1)0.003 (1)0.012 (1)0.009 (1)
C170.048 (2)0.066 (2)0.049 (2)0.000 (2)0.006 (1)0.010 (1)
C180.041 (2)0.095 (3)0.075 (2)0.001 (2)0.000 (2)0.020 (2)
C190.042 (2)0.085 (3)0.102 (3)0.017 (2)0.026 (2)0.036 (2)
C200.058 (2)0.072 (2)0.086 (3)0.020 (2)0.036 (2)0.014 (2)
C210.047 (2)0.058 (2)0.057 (2)0.007 (1)0.020 (1)0.004 (1)
Geometric parameters (Å, º) top
P1—O11.483 (2)C17—C181.375 (6)
P1—C31.808 (3)C18—C191.368 (7)
P1—C101.799 (3)C19—C201.376 (5)
P1—C161.805 (3)C20—C211.376 (5)
C1—C21.290 (5)C1—H10.9805
C2—C31.316 (5)C1—H20.9590
C3—C41.492 (4)C5—H50.9700
C4—C51.385 (4)C6—H60.9700
C4—C91.391 (5)C7—H70.9700
C5—C61.388 (6)C8—H80.9700
C6—C71.373 (7)C9—H90.9700
C7—C81.366 (5)C11—H110.9700
C8—C91.383 (5)C12—H120.9700
C10—C111.386 (4)C13—H130.9700
C10—C151.393 (4)C14—H140.9700
C11—C121.384 (4)C15—H150.9700
C12—C131.366 (5)C17—H170.9700
C13—C141.382 (6)C18—H180.9700
C14—C151.380 (5)C19—H190.9700
C16—C171.388 (4)C20—H200.9700
C16—C211.389 (5)C21—H210.9700
C3—P1—O1113.9 (1)H1—C1—C2119.5193
C10—P1—O1112.3 (1)H2—C1—C2117.1031
C16—P1—O1111.3 (1)H2—C1—H1123.1455
P1—C3—C2116.5 (2)C4—C5—H5119.9554
P1—C3—C4121.3 (2)C4—C9—H9119.5967
C10—P1—C3105.6 (1)H5—C5—C6119.6936
C16—P1—C3105.9 (1)C5—C6—H6119.8856
P1—C10—C11118.2 (2)H6—C6—C7119.6977
P1—C10—C15122.6 (2)C6—C7—H7120.2158
C16—P1—C10107.3 (1)C7—C8—H8119.9838
P1—C16—C17116.8 (3)H7—C7—C8119.8015
P1—C16—C21124.1 (2)C8—C9—H9119.4185
C1—C2—C3179.2 (3)H8—C8—C9120.0046
C2—C3—C4122.2 (2)C10—C11—H11120.0109
C3—C4—C9121.8 (2)C10—C15—H15120.2896
C3—C4—C5120.0 (3)H11—C11—C12119.7037
C9—C4—C5118.2 (3)C11—C12—H12119.7873
C4—C5—C6120.4 (4)H12—C12—C13119.8370
C4—C9—C8121.0 (3)C12—C13—H13120.0249
C5—C6—C7120.4 (4)C13—C14—H14119.7412
C6—C7—C8120.0 (4)H13—C13—C14120.1332
C7—C8—C9120.0 (4)C14—C15—H15119.9015
C15—C10—C11119.2 (3)H14—C14—C15119.7325
C10—C11—C12120.3 (3)C16—C17—H17119.9915
C10—C15—C14119.8 (3)C16—C21—H21120.1473
C11—C12—C13120.4 (4)H17—C17—C18119.7607
C12—C13—C14119.8 (3)C17—C18—H18120.0746
C13—C14—C15120.5 (3)H18—C18—C19120.0540
C21—C16—C17119.1 (3)C18—C19—H19119.4929
C16—C17—C18120.2 (4)C19—C20—H20120.1052
C16—C21—C20120.4 (3)H19—C19—C20119.5340
C17—C18—C19119.9 (3)C20—C21—H21119.4185
C18—C19—C20121.0 (4)H20—C20—C21120.5088
C19—C20—C21119.4 (4)
O(1)—P(1)—C(3)—C(2)122.1 (2)C(9)—C(4)—C(5)—C(6)1.2 (4)
O(1)—P(1)—C(3)—C(4)56.4 (2)C(3)—C(4)—C(9)—C(8)178.8 (3)
C(10)—P(1)—C(3)—C(2)114.2 (2)C(5)—C(4)—C(9)—C(8)1.8 (4)
C(10)—P(1)—C(3)—C(4)67.3 (2)C(4)—C(5)—C(6)—C(7)0.5 (5)
C(16)—P(1)—C(3)—C(2)0.6 (2)C(5)—C(6)—C(7)—C(8)0.4 (6)
C(16)—P(1)—C(3)—C(4)179.1 (2)C(6)—C(7)—C(8)—C(9)1.1 (6)
O(1)—P(1)—C(10)—C(11)21.1 (3)C(7)—C(8)—C(9)—C(4)1.8 (5)
O(1)—P(1)—C(10)—C(15)159.4 (2)P(1)—C(10)—C(11)—C(12)179.5 (3)
C(3)—P(1)—C(10)—C(11)145.8 (2)C(15)—C(10)—C(11)—C(12)0.0 (4)
C(3)—P(1)—C(10)—C(15)34.7 (3)P(1)—C(10)—C(15)—C(14)179.5 (3)
C(16)—P(1)—C(10)—C(11)101.5 (2)C(11)—C(10)—C(15)—C(14)0.0 (4)
C(16)—P(1)—C(10)—C(15)78.0 (3)C(10)—C(11)—C(12)—C(13)0.6 (5)
O(1)—P(1)—C(16)—C(17)14.9 (3)C(11)—C(12)—C(13)—C(14)1.1 (6)
O(1)—P(1)—C(16)—C(21)164.7 (2)C(12)—C(13)—C(14)—C(15)1.1 (6)
C(3)—P(1)—C(16)—C(17)109.4 (2)C(13)—C(14)—C(15)—C(10)0.5 (5)
C(3)—P(1)—C(16)—C(21)71.0 (3)P(1)—C(16)—C(17)—C(18)179.9 (3)
C(10)—P(1)—C(16)—C(17)138.1 (2)C(21)—C(16)—C(17)—C(18)0.3 (5)
C(10)—P(1)—C(16)—C(21)41.5 (3)P(1)—C(16)—C(21)—C(20)179.1 (3)
P(1)—C(3)—C(4)—C(5)176.9 (2)C(17)—C(16)—C(21)—C(20)0.4 (5)
P(1)—C(3)—C(4)—C(9)2.5 (4)C(16)—C(17)—C(18)—C(19)0.9 (6)
C(2)—C(3)—C(4)—C(5)1.5 (4)C(17)—C(18)—C(19)—C(20)0.9 (7)
C(2)—C(3)—C(4)—C(9)179.1 (3)C(18)—C(19)—C(20)—C(21)0.2 (5)
C(3)—C(4)—C(5)—C(6)179.4 (3)C(19)—C(20)—C(21)—C(16)0.5 (6)
 

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