The title compound, C
18H
19OP, has a mirror plane passing through the phosphinoyl and acetylene groups. There is a weak intermolecular C—H
O interaction.
Supporting information
CCDC reference: 259092
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
Crystal data top
C18H19OP | F(000) = 600.00 |
Mr = 282.32 | Dx = 1.207 Mg m−3 |
Orthorhombic, Cmc21 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: C 2c -2 | Cell parameters from 8920 reflections |
a = 14.4742 (7) Å | θ = 2.5–27.5° |
b = 9.5767 (7) Å | µ = 0.17 mm−1 |
c = 11.2075 (6) Å | T = 296 K |
V = 1553.5 (2) Å3 | Platelet, colorless |
Z = 4 | 0.60 × 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-1 | Rint = 0.036 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
Tmin = 0.873, Tmax = 0.983 | k = −12→12 |
7260 measured reflections | l = −13→14 |
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) = 0.088 | Δρmax = 0.29 e Å−3 |
S = 1.00 | Δρmin = −0.33 e Å−3 |
1309 reflections | Absolute structure: (Flack, 1983), 632 Friedel pairs |
102 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
P1 | 0.5000 | 0.58355 (8) | 0.35768 (9) | 0.0410 (2) | |
O1 | 0.5000 | 0.6571 (3) | 0.4734 (2) | 0.0557 (7) | |
C1 | 0.5000 | 0.2789 (3) | 0.3852 (3) | 0.048 (1) | |
C2 | 0.5000 | 0.4020 (3) | 0.3694 (4) | 0.0483 (8) | |
C3 | 0.3987 (1) | 0.6231 (2) | 0.2707 (2) | 0.0399 (5) | |
C4 | 0.3396 (2) | 0.7249 (3) | 0.3147 (2) | 0.0548 (7) | |
C5 | 0.2606 (2) | 0.7590 (3) | 0.2540 (3) | 0.0697 (9) | |
C6 | 0.2402 (2) | 0.6943 (3) | 0.1485 (3) | 0.0655 (9) | |
C7 | 0.2978 (2) | 0.5947 (3) | 0.1034 (3) | 0.0625 (8) | |
C8 | 0.3773 (2) | 0.5582 (2) | 0.1647 (2) | 0.0525 (7) | |
C9 | 0.5000 | 0.1272 (4) | 0.4057 (3) | 0.0455 (9) | |
C10 | 0.50000 (1) | 0.0535 (4) | 0.2855 (4) | 0.070 (1) | |
C11 | 0.4137 (2) | 0.0888 (3) | 0.4755 (3) | 0.0711 (9) | |
H4 | 0.3550 | 0.7721 | 0.3887 | 0.066* | |
H5 | 0.2191 | 0.8298 | 0.2849 | 0.084* | |
H6 | 0.1842 | 0.7185 | 0.1058 | 0.079* | |
H7 | 0.2829 | 0.5490 | 0.0286 | 0.075* | |
H8 | 0.4189 | 0.4874 | 0.1337 | 0.063* | |
H102 | 0.4455 | 0.0813 | 0.2412 | 0.084* | |
H101 | 0.5000 | −0.0470 | 0.2965 | 0.084* | |
H111 | 0.4270 | 0.0939 | 0.5603 | 0.086* | |
H112 | 0.3641 | 0.1532 | 0.4563 | 0.086* | |
H113 | 0.3950 | −0.0055 | 0.4551 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0530 (4) | 0.0325 (4) | 0.0376 (4) | 0.0000 | 0.0000 | 0.0042 (4) |
O1 | 0.075 (2) | 0.052 (2) | 0.041 (1) | 0.0000 | 0.0000 | −0.002 (1) |
C1 | 0.055 (2) | 0.044 (2) | 0.046 (2) | 0.0000 | 0.0000 | 0.005 (1) |
C2 | 0.058 (2) | 0.039 (2) | 0.048 (2) | 0.0000 | 0.0000 | 0.006 (2) |
C3 | 0.044 (1) | 0.034 (1) | 0.042 (1) | −0.0029 (9) | 0.005 (1) | 0.0076 (8) |
C4 | 0.064 (1) | 0.050 (1) | 0.051 (1) | 0.008 (1) | 0.007 (1) | −0.002 (1) |
C5 | 0.062 (2) | 0.072 (2) | 0.076 (2) | 0.020 (1) | 0.009 (2) | 0.012 (2) |
C6 | 0.050 (2) | 0.079 (2) | 0.067 (2) | 0.002 (1) | −0.003 (1) | 0.021 (1) |
C7 | 0.061 (1) | 0.072 (2) | 0.055 (2) | −0.012 (1) | −0.008 (1) | 0.005 (1) |
C8 | 0.056 (1) | 0.049 (1) | 0.053 (1) | −0.003 (1) | −0.001 (1) | −0.004 (1) |
C9 | 0.055 (2) | 0.034 (2) | 0.048 (2) | 0.0000 | 0.0000 | 0.007 (1) |
C10 | 0.099 (3) | 0.053 (2) | 0.057 (3) | 0.0000 | 0.0000 | −0.009 (2) |
C11 | 0.076 (2) | 0.052 (2) | 0.085 (2) | −0.005 (1) | 0.019 (2) | 0.012 (1) |
Geometric parameters (Å, º) top
P1—O1 | 1.476 (2) | C9—C11 | 1.519 (4) |
P1—C2 | 1.744 (3) | C9—C11i | 1.519 (4) |
P1—C3 | 1.801 (2) | C4—H4 | 0.9700 |
P1—C3i | 1.801 (2) | C5—H5 | 0.9700 |
C1—C2 | 1.192 (4) | C6—H6 | 0.9699 |
C1—C9 | 1.472 (5) | C7—H7 | 0.9700 |
C3—C4 | 1.387 (3) | C8—H8 | 0.9700 |
C3—C8 | 1.376 (3) | C10—H102 | 0.9700 |
C4—C5 | 1.370 (4) | C10—H102i | 0.9700 |
C5—C6 | 1.367 (4) | C10—H101 | 0.9700 |
C6—C7 | 1.364 (4) | C10—H101i | 0.9700 |
C7—C8 | 1.385 (4) | C11—H111 | 0.9700 |
C9—C10 | 1.521 (5) | C11—H112 | 0.9700 |
C9—C10i | 1.521 (5) | C11—H113 | 0.9700 |
| | | |
C2—P1—O1 | 114.2 (2) | C3—C8—H8 | 119.0518 |
C3—P1—O1 | 112.04 (9) | H4—C4—C5 | 120.2290 |
C3i—P1—O1 | 112.04 (9) | C4—C5—H5 | 120.4393 |
P1—C2—C1 | 175.8 (4) | H5—C5—C6 | 119.4669 |
C3—P1—C2 | 104.5 (1) | C5—C6—H6 | 119.9531 |
C3i—P1—C2 | 104.5 (1) | C6—C7—H7 | 120.0094 |
C3i—P1—C3 | 109.0 (1) | H6—C6—C7 | 119.6636 |
P1—C3—C4 | 117.2 (2) | C7—C8—H8 | 120.9117 |
P1—C3—C8 | 123.7 (2) | H7—C7—C8 | 119.9652 |
P1—C3i—C4i | 117.2 (2) | C9—C10—H102 | 109.0384 |
P1—C3i—C8i | 123.7 (2) | C9—C10—H102i | 109.0384 |
C9—C1—C2 | 179.5 (4) | C9—C10—H101 | 110.3236 |
C1—C9—C10 | 108.6 (3) | C9—C11—H111 | 109.1616 |
C1—C9—C11 | 108.6 (2) | C9—C11—H112 | 109.8444 |
C1—C9—C11i | 108.6 (2) | C9—C11—H113 | 109.4044 |
C8—C3—C4 | 119.1 (2) | C9—C11i—H111i | 109.1616 |
C3—C4—C5 | 120.4 (2) | C9—C11i—H112i | 109.8444 |
C3—C8—C7 | 120.0 (2) | C9—C11i—H113i | 109.4044 |
C4—C5—C6 | 120.1 (3) | H102i—C10—H102 | 108.8849 |
C5—C6—C7 | 120.4 (3) | H101—C10—H102 | 109.7640 |
C6—C7—C8 | 120.0 (3) | H101—C10—H102i | 109.7640 |
C11—C9—C10 | 110.1 (2) | H112—C11—H111 | 109.4717 |
C11i—C9—C10 | 110.1 (2) | H113—C11—H111 | 109.4678 |
C11i—C9—C11 | 110.6 (3) | H113—C11—H112 | 109.4765 |
C3—C4—H4 | 119.4125 | | |
| | | |
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···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1ii | 0.97 | 2.55 | 3.464 (3) | 156 |
Symmetry code: (ii) x, −y+1, z−1/2. |