Download citation
Download citation
link to html
The title compound, C18H19OP, has a mirror plane passing through the phosphinoyl and acetyl­ene groups. There is a weak intermolecular C—H...O interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027217/ob6424sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027217/ob6424Isup2.hkl
Contains datablock I

CCDC reference: 259092

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.088
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C9
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1688 Count of symmetry unique reflns 983 Completeness (_total/calc) 171.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 705 Fraction of Friedel pairs measured 0.717 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 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
C18H19OPF(000) = 600.00
Mr = 282.32Dx = 1.207 Mg m3
Orthorhombic, Cmc21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: C 2c -2Cell parameters from 8920 reflections
a = 14.4742 (7) Åθ = 2.5–27.5°
b = 9.5767 (7) ŵ = 0.17 mm1
c = 11.2075 (6) ÅT = 296 K
V = 1553.5 (2) Å3Platelet, colorless
Z = 40.60 × 0.20 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1309 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.036
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1818
Tmin = 0.873, Tmax = 0.983k = 1212
7260 measured reflectionsl = 1314
1688 independent reflections
Refinement top
Refinement on F2 w = 1/[0.001Fo2 + 1.1σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.036(Δ/σ)max < 0.001
wR(F2) = 0.088Δρmax = 0.29 e Å3
S = 1.00Δρmin = 0.33 e Å3
1309 reflectionsAbsolute structure: (Flack, 1983), 632 Friedel pairs
102 parametersAbsolute structure parameter: 0.01 (1)
H-atom parameters constrained
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
P10.50000.58355 (8)0.35768 (9)0.0410 (2)
O10.50000.6571 (3)0.4734 (2)0.0557 (7)
C10.50000.2789 (3)0.3852 (3)0.048 (1)
C20.50000.4020 (3)0.3694 (4)0.0483 (8)
C30.3987 (1)0.6231 (2)0.2707 (2)0.0399 (5)
C40.3396 (2)0.7249 (3)0.3147 (2)0.0548 (7)
C50.2606 (2)0.7590 (3)0.2540 (3)0.0697 (9)
C60.2402 (2)0.6943 (3)0.1485 (3)0.0655 (9)
C70.2978 (2)0.5947 (3)0.1034 (3)0.0625 (8)
C80.3773 (2)0.5582 (2)0.1647 (2)0.0525 (7)
C90.50000.1272 (4)0.4057 (3)0.0455 (9)
C100.50000 (1)0.0535 (4)0.2855 (4)0.070 (1)
C110.4137 (2)0.0888 (3)0.4755 (3)0.0711 (9)
H40.35500.77210.38870.066*
H50.21910.82980.28490.084*
H60.18420.71850.10580.079*
H70.28290.54900.02860.075*
H80.41890.48740.13370.063*
H1020.44550.08130.24120.084*
H1010.50000.04700.29650.084*
H1110.42700.09390.56030.086*
H1120.36410.15320.45630.086*
H1130.39500.00550.45510.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0530 (4)0.0325 (4)0.0376 (4)0.00000.00000.0042 (4)
O10.075 (2)0.052 (2)0.041 (1)0.00000.00000.002 (1)
C10.055 (2)0.044 (2)0.046 (2)0.00000.00000.005 (1)
C20.058 (2)0.039 (2)0.048 (2)0.00000.00000.006 (2)
C30.044 (1)0.034 (1)0.042 (1)0.0029 (9)0.005 (1)0.0076 (8)
C40.064 (1)0.050 (1)0.051 (1)0.008 (1)0.007 (1)0.002 (1)
C50.062 (2)0.072 (2)0.076 (2)0.020 (1)0.009 (2)0.012 (2)
C60.050 (2)0.079 (2)0.067 (2)0.002 (1)0.003 (1)0.021 (1)
C70.061 (1)0.072 (2)0.055 (2)0.012 (1)0.008 (1)0.005 (1)
C80.056 (1)0.049 (1)0.053 (1)0.003 (1)0.001 (1)0.004 (1)
C90.055 (2)0.034 (2)0.048 (2)0.00000.00000.007 (1)
C100.099 (3)0.053 (2)0.057 (3)0.00000.00000.009 (2)
C110.076 (2)0.052 (2)0.085 (2)0.005 (1)0.019 (2)0.012 (1)
Geometric parameters (Å, º) top
P1—O11.476 (2)C9—C111.519 (4)
P1—C21.744 (3)C9—C11i1.519 (4)
P1—C31.801 (2)C4—H40.9700
P1—C3i1.801 (2)C5—H50.9700
C1—C21.192 (4)C6—H60.9699
C1—C91.472 (5)C7—H70.9700
C3—C41.387 (3)C8—H80.9700
C3—C81.376 (3)C10—H1020.9700
C4—C51.370 (4)C10—H102i0.9700
C5—C61.367 (4)C10—H1010.9700
C6—C71.364 (4)C10—H101i0.9700
C7—C81.385 (4)C11—H1110.9700
C9—C101.521 (5)C11—H1120.9700
C9—C10i1.521 (5)C11—H1130.9700
C2—P1—O1114.2 (2)C3—C8—H8119.0518
C3—P1—O1112.04 (9)H4—C4—C5120.2290
C3i—P1—O1112.04 (9)C4—C5—H5120.4393
P1—C2—C1175.8 (4)H5—C5—C6119.4669
C3—P1—C2104.5 (1)C5—C6—H6119.9531
C3i—P1—C2104.5 (1)C6—C7—H7120.0094
C3i—P1—C3109.0 (1)H6—C6—C7119.6636
P1—C3—C4117.2 (2)C7—C8—H8120.9117
P1—C3—C8123.7 (2)H7—C7—C8119.9652
P1—C3i—C4i117.2 (2)C9—C10—H102109.0384
P1—C3i—C8i123.7 (2)C9—C10—H102i109.0384
C9—C1—C2179.5 (4)C9—C10—H101110.3236
C1—C9—C10108.6 (3)C9—C11—H111109.1616
C1—C9—C11108.6 (2)C9—C11—H112109.8444
C1—C9—C11i108.6 (2)C9—C11—H113109.4044
C8—C3—C4119.1 (2)C9—C11i—H111i109.1616
C3—C4—C5120.4 (2)C9—C11i—H112i109.8444
C3—C8—C7120.0 (2)C9—C11i—H113i109.4044
C4—C5—C6120.1 (3)H102i—C10—H102108.8849
C5—C6—C7120.4 (3)H101—C10—H102109.7640
C6—C7—C8120.0 (3)H101—C10—H102i109.7640
C11—C9—C10110.1 (2)H112—C11—H111109.4717
C11i—C9—C10110.1 (2)H113—C11—H111109.4678
C11i—C9—C11110.6 (3)H113—C11—H112109.4765
C3—C4—H4119.4125
O(1)—P(1)—C(3)—C(4)6.4 (2)P(1)—C(3)—C(8)—C(7)179.9 (2)
O(1)—P(1)—C(3)—C(8)173.5 (3)C(4)—C(3)—C(8)—C(7)0.0 (3)
C(2)—P(1)—C(3)—C(4)130.5 (3)C(3)—C(4)—C(5)—C(6)1.0 (4)
C(2)—P(1)—C(3)—C(8)49.4 (4)C(4)—C(5)—C(6)—C(7)0.5 (5)
P(1)—C(3)—C(4)—C(5)179.1 (2)C(5)—C(6)—C(7)—C(8)0.2 (4)
C(8)—C(3)—C(4)—C(5)0.7 (4)C(6)—C(7)—C(8)—C(3)0.5 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1ii0.972.553.464 (3)156
Symmetry code: (ii) x, y+1, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds