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The crystal structure of 10-[2,5-bis(2,3-epoxy-1-prop­oxy)­phenyl]-9-oxa-10-phosphaphenanthren-10-one has been studied by single-crystal X-ray diffraction. The unit cell of C24H21O6P, Mr = 436.4, is triclinic, P1, with a = 8.507 (3), b = 10.613 (4), c = 12.457 (3) Å, α = 80.05 (3), β = 71.38 (2), γ = 76.69 (3)°, V = 1031.1 (6) Å3, Z = 2, Dx = 1.406 Mg m−3 and μ(Mo Kα) = 0.17 mm−1. The final R (wR) is 0.063 (0.057) {w = 1/[σ2(F) + 0.0004F2]} for 3619 unique reflections measured at 295 K. The aryl phosphinate group bonded to the central phenyl ring comes close to one of the two glycidyl ether groups, the epoxide ring of which is ordered. The epoxide ring far from the aryl phosphinate group is disordered. The NMR chemical shifts of the protons of the glycidyl ether group close to the aryl phosphinate group are reduced by the `ring-current effect'.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, I

sft

Structure factor file (SHELXL table format)
Supplementary material

CCDC reference: 134779

Comment top

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Experimental top

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Computing details top

Data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS; data reduction: NRCVAX DATRD2; program(s) used to solve structure: NRCVAX SOLVER; program(s) used to refine structure: NRCVAX LSTSQ; molecular graphics: NRCVAX ORTEP; software used to prepare material for publication: NRCVAX TABLES.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
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Crystal data top
C24H21O6PF(000) = 456.37
Mr = 436.40? #Insert any comments here.
Triclinic, P1Dx = 1.406 Mg m3
a = 8.507 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.613 (4) ÅCell parameters from 25 reflections
c = 12.457 (3) Åθ = 7.4–10.9°
α = 80.05 (3)°µ = 0.17 mm1
β = 71.38 (2)°T = 295 K
γ = 76.69 (3)°Block, colorless
V = 1031.1 (6) Å30.50 × 0.38 × 0.20 mm
Z = 2
Data collection top
Enraf-Nonius CAD4
diffractometer
2634 reflections with Inet > 2.0σ(Inet)
Radiation source: xray tubeRint = 0.010
Graphite monochromatorθmax = 24.9°, θmin = 0.0°
θ/2θ scan b/P/bh = 910
Absorption correction: empirical (using intensity measurements)
?
k = 012
Tmin = 0.918, Tmax = 0.953l = 1414
3632 measured reflections3 standard reflections every 60 min
3619 independent reflections intensity decay: 0.0%
Refinement top
Refinement on F1/(σ2(F) + 0.0004F2)
Least-squares matrix: block diagonal per atom(Δ/σ)max = 0.010
R[F2 > 2σ(F2)] = 0.063Δρmax = 4.30 e Å3
wR(F2) = 0.057Δρmin = 2.50 e Å3
3619 reflectionsExtinction correction: Larson
299 parametersExtinction coefficient: 624 (213)
Crystal data top
C24H21O6Pγ = 76.69 (3)°
Mr = 436.40V = 1031.1 (6) Å3
Triclinic, P1Z = 2
a = 8.507 (3) ÅMo Kα radiation
b = 10.613 (4) ŵ = 0.17 mm1
c = 12.457 (3) ÅT = 295 K
α = 80.05 (3)°0.50 × 0.38 × 0.20 mm
β = 71.38 (2)°
Data collection top
Enraf-Nonius CAD4
diffractometer
2634 reflections with Inet > 2.0σ(Inet)
Absorption correction: empirical (using intensity measurements)
?
Rint = 0.010
Tmin = 0.918, Tmax = 0.9533 standard reflections every 60 min
3632 measured reflections intensity decay: 0.0%
3619 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063299 parameters
wR(F2) = 0.057Δρmax = 4.30 e Å3
3619 reflectionsΔρmin = 2.50 e Å3
Special details top

Experimental. ? #Insert any special details here.

Refinement. ? #Insert any special details here.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P0.91830 (7)0.72952 (5)0.42866 (4)0.0383 (3)
O10.9139 (2)0.88184 (13)0.41924 (11)0.0509 (10)
O21.01965 (18)0.65441 (14)0.50183 (12)0.0500 (9)
O30.62925 (19)0.88473 (16)0.34941 (13)0.0628 (10)
O40.4335 (2)0.50935 (19)0.70245 (17)0.0863 (13)
O50.6501 (3)1.0762 (2)0.13093 (17)0.0982 (17)
O60.3526 (3)0.3511 (2)0.93426 (15)0.0861 (14)
C10.9910 (2)0.69429 (19)0.28446 (17)0.0388 (11)
C20.9979 (3)0.5676 (2)0.26422 (19)0.0539 (15)
C31.0522 (4)0.5342 (2)0.1545 (2)0.0658 (18)
C41.0977 (3)0.6271 (2)0.0647 (2)0.0621 (17)
C51.0911 (3)0.7526 (2)0.08321 (18)0.0512 (14)
C61.0400 (2)0.78933 (19)0.19331 (17)0.0390 (11)
C71.0431 (2)0.92132 (19)0.21477 (17)0.0387 (11)
C81.1068 (3)1.0145 (2)0.12615 (18)0.0537 (14)
C91.1138 (3)1.1359 (2)0.1470 (2)0.0637 (16)
C101.0608 (3)1.1689 (2)0.2571 (2)0.0555 (14)
C110.9971 (3)1.0809 (2)0.34569 (18)0.0453 (12)
C120.9875 (2)0.96034 (19)0.32373 (17)0.0379 (11)
C130.7009 (3)0.7147 (2)0.48413 (17)0.0417 (12)
C140.5772 (3)0.7927 (2)0.43766 (18)0.0481 (12)
C150.4131 (3)0.7708 (3)0.4793 (2)0.0609 (16)
C160.3723 (3)0.6749 (3)0.5663 (2)0.0655 (16)
C170.4916 (3)0.5992 (2)0.6148 (2)0.0573 (14)
C180.6568 (3)0.6177 (2)0.57315 (19)0.0492 (13)
C190.5078 (3)0.9919 (3)0.3251 (2)0.0695 (16)
C200.5989 (4)1.0917 (3)0.2456 (2)0.0769 (19)
C210.5268 (4)1.1872 (3)0.1737 (3)0.097 (2)
C220.5480 (4)0.4195 (3)0.7485 (3)0.084 (2)
C230.4298 (5)0.3256 (4)0.8195 (3)0.061 (3)
C240.4840 (6)0.2380 (6)0.9056 (4)0.092 (4)
C23'0.4999 (8)0.3175 (7)0.8488 (6)0.072 (4)
C24'0.3475 (8)0.2776 (6)0.8532 (5)0.063 (4)
H20.9640.5030.3280.0657*
H31.0600.4450.1410.0764*
H41.1350.6040.0130.0735*
H51.1210.8170.0190.0623*
H81.1460.9920.0490.0621*
H91.1581.1990.0840.0698*
H101.0691.2540.2720.0634*
H110.9591.1030.4240.0565*
H150.3280.8250.4460.0693*
H160.2570.6590.5950.0729*
H180.7430.5630.6050.0587*
H19a0.4590.9900.2740.0935*
H19b0.4341.0290.3950.0708*
H200.6841.1190.2740.0865*
H21a0.5471.2730.1430.0988*
H21b0.4141.1880.1760.0988*
H22a0.6340.3780.6870.0848*
H22b0.5890.4670.7920.0848*
H230.3660.2950.7810.0685*
H24a0.4640.1500.9260.0914*
H24b0.5990.2320.9130.0914*
H23'0.5910.2470.8670.0807*
H24'a0.3310.1900.8690.0736*
H24'b0.2930.3180.7930.0736*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0412 (3)0.0364 (3)0.0391 (3)0.0121 (2)0.0130 (2)0.0002 (2)
O10.0743 (10)0.0405 (8)0.0379 (8)0.0217 (7)0.0088 (7)0.0040 (6)
O20.0481 (8)0.0549 (9)0.0510 (9)0.0146 (7)0.0224 (7)0.0055 (7)
O30.0507 (9)0.0657 (11)0.0572 (10)0.0032 (8)0.0131 (8)0.0085 (8)
O40.0670 (12)0.0783 (13)0.0946 (14)0.0305 (10)0.0007 (11)0.0164 (11)
O50.1186 (17)0.0961 (16)0.0604 (12)0.0238 (13)0.0043 (12)0.0105 (11)
O60.0883 (14)0.0970 (15)0.0603 (12)0.0291 (11)0.0048 (10)0.0101 (10)
C10.0392 (11)0.0353 (11)0.0444 (11)0.0073 (9)0.0152 (9)0.0050 (9)
C20.0719 (16)0.0387 (12)0.0527 (13)0.0134 (11)0.0194 (12)0.0028 (10)
C30.099 (2)0.0427 (14)0.0630 (16)0.0160 (13)0.0282 (15)0.0115 (12)
C40.0859 (18)0.0595 (15)0.0453 (13)0.0144 (13)0.0198 (13)0.0151 (11)
C50.0646 (14)0.0485 (13)0.0425 (12)0.0173 (11)0.0144 (11)0.0037 (10)
C60.0377 (10)0.0398 (11)0.0400 (11)0.0080 (9)0.0113 (9)0.0043 (9)
C70.0376 (10)0.0350 (11)0.0431 (11)0.0076 (8)0.0113 (9)0.0032 (9)
C80.0629 (14)0.0487 (13)0.0433 (13)0.0169 (11)0.0035 (11)0.0022 (10)
C90.0806 (17)0.0437 (13)0.0584 (15)0.0246 (12)0.0047 (13)0.0039 (11)
C100.0649 (15)0.0352 (12)0.0643 (15)0.0179 (11)0.0103 (12)0.0046 (11)
C110.0493 (12)0.0383 (12)0.0497 (12)0.0093 (10)0.0133 (10)0.0090 (10)
C120.0358 (10)0.0361 (11)0.0417 (11)0.0087 (8)0.0118 (9)0.0004 (9)
C130.0410 (11)0.0406 (11)0.0434 (11)0.0080 (9)0.0104 (9)0.0070 (9)
C140.0454 (12)0.0499 (13)0.0450 (12)0.0029 (10)0.0104 (10)0.0082 (10)
C150.0393 (12)0.0772 (17)0.0623 (15)0.0032 (11)0.0135 (11)0.0104 (13)
C160.0391 (13)0.0768 (18)0.0762 (17)0.0129 (12)0.0038 (12)0.0190 (14)
C170.0519 (13)0.0536 (14)0.0598 (15)0.0212 (11)0.0015 (11)0.0077 (11)
C180.0477 (12)0.0452 (13)0.0519 (13)0.0114 (10)0.0099 (10)0.0025 (10)
C190.0677 (16)0.0687 (17)0.0514 (14)0.0185 (13)0.0109 (12)0.0065 (13)
C200.088 (2)0.0664 (17)0.0721 (18)0.0075 (15)0.0336 (16)0.0075 (14)
C210.081 (2)0.097 (2)0.095 (2)0.0012 (18)0.0298 (18)0.0199 (19)
C220.094 (2)0.0631 (18)0.0715 (18)0.0211 (16)0.0090 (16)0.0011 (14)
C230.061 (3)0.067 (3)0.055 (2)0.021 (2)0.012 (2)0.001 (2)
C240.071 (3)0.103 (4)0.076 (3)0.005 (3)0.012 (3)0.024 (3)
C23'0.054 (4)0.086 (5)0.071 (4)0.020 (3)0.022 (3)0.025 (4)
C24'0.061 (4)0.066 (4)0.061 (4)0.023 (3)0.005 (3)0.010 (3)
Geometric parameters (Å, º) top
P—O11.5932 (16)C7—C81.406 (3)
P—O21.4641 (15)C7—C121.390 (3)
P—C11.779 (2)C8—C91.376 (3)
P—C131.790 (2)C9—C101.381 (4)
O1—C121.387 (2)C10—C111.371 (3)
O3—C141.370 (3)C11—C121.379 (3)
O3—C191.412 (3)C13—C141.396 (3)
O4—C171.363 (3)C13—C181.396 (3)
O4—C221.389 (4)C14—C151.384 (3)
O5—C201.381 (3)C15—C161.369 (4)
O5—C211.437 (4)C16—C171.375 (4)
O6—C231.415 (4)C17—C181.382 (3)
O6—C241.447 (6)C19—C201.494 (4)
O6—C23'1.380 (7)C20—C211.399 (4)
O6—C24'1.395 (7)C22—C231.541 (5)
C1—C21.395 (3)C22—C23'1.520 (7)
C1—C61.406 (3)C23—C241.415 (6)
C2—C31.376 (3)C23—C23'0.776 (8)
C3—C41.375 (4)C23—C24'0.910 (7)
C4—C51.377 (3)C24—C23'1.008 (8)
C5—C61.395 (3)C24—C24'1.455 (8)
C6—C71.478 (3)C23'—C24'1.436 (9)
O1—P—O2111.96 (9)O4—C17—C16115.3 (2)
O1—P—C1103.87 (9)O4—C17—C18125.2 (2)
O1—P—C13104.14 (9)C16—C17—C18119.5 (2)
O2—P—C1115.46 (9)C13—C18—C17120.0 (2)
O2—P—C13112.41 (9)O3—C19—C20108.1 (2)
C1—P—C13108.07 (10)O5—C20—C19116.8 (3)
P—O1—C12127.02 (13)O5—C20—C2162.3 (2)
C14—O3—C19118.50 (18)C19—C20—C21123.4 (3)
C17—O4—C22119.2 (2)O5—C21—C2058.26 (19)
C20—O5—C2159.49 (19)O4—C22—C2398.6 (3)
C23—O6—C2459.3 (3)O4—C22—C23'124.6 (3)
C23—O6—C23'32.2 (3)C23—C22—C23'29.3 (3)
C23—O6—C24'37.8 (3)O6—C23—C22114.2 (3)
C24—O6—C23'41.7 (3)O6—C23—C2461.5 (3)
C24—O6—C24'61.5 (4)O6—C23—C23'71.4 (6)
C23'—O6—C24'62.3 (4)O6—C23—C24'69.9 (5)
P—C1—C2117.50 (16)C22—C23—C24116.7 (4)
P—C1—C6122.00 (15)C22—C23—C23'73.9 (6)
C2—C1—C6120.51 (19)C22—C23—C24'169.4 (6)
C1—C2—C3120.4 (2)C24—C23—C23'43.7 (6)
C2—C3—C4119.6 (2)C24—C23—C24'73.9 (5)
C3—C4—C5120.8 (2)C23'—C23—C24'116.6 (8)
C4—C5—C6121.2 (2)O6—C24—C2359.2 (3)
C1—C6—C5117.53 (18)O6—C24—C23'65.6 (5)
C1—C6—C7120.62 (18)O6—C24—C24'57.5 (3)
C5—C6—C7121.81 (18)C23—C24—C23'32.1 (4)
C6—C7—C8121.96 (18)C23—C24—C24'37.0 (3)
C6—C7—C12122.35 (17)C23'—C24—C24'68.6 (5)
C8—C7—C12115.67 (18)O6—C23'—C22117.7 (5)
C7—C8—C9121.7 (2)O6—C23'—C2376.4 (6)
C8—C9—C10120.4 (2)O6—C23'—C2472.7 (5)
C9—C10—C11119.6 (2)O6—C23'—C24'59.4 (4)
C10—C11—C12119.6 (2)C22—C23'—C2376.8 (6)
O1—C12—C7122.51 (17)C22—C23'—C24169.2 (8)
O1—C12—C11114.45 (18)C22—C23'—C24'111.3 (5)
C7—C12—C11123.02 (18)C23—C23'—C24104.3 (8)
P—C13—C14122.03 (16)C23—C23'—C24'34.5 (5)
P—C13—C18118.26 (16)C24—C23'—C24'70.6 (6)
C14—C13—C18119.64 (19)O6—C24'—C2372.3 (5)
O3—C14—C13116.71 (19)O6—C24'—C2461.0 (4)
O3—C14—C15123.9 (2)O6—C24'—C23'58.3 (4)
C13—C14—C15119.4 (2)C23—C24'—C2469.2 (5)
C14—C15—C16120.2 (2)C23—C24'—C23'28.9 (4)
C15—C16—C17121.2 (2)C24—C24'—C23'40.8 (4)

Experimental details

Crystal data
Chemical formulaC24H21O6P
Mr436.40
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.507 (3), 10.613 (4), 12.457 (3)
α, β, γ (°)80.05 (3), 71.38 (2), 76.69 (3)
V3)1031.1 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.50 × 0.38 × 0.20
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
Tmin, Tmax0.918, 0.953
No. of measured, independent and
observed [Inet > 2.0σ(Inet)] reflections
3632, 3619, 2634
Rint0.010
(sin θ/λ)max1)0.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.057, ?
No. of reflections3619
No. of parameters299
No. of restraints?
Δρmax, Δρmin (e Å3)4.30, 2.50

Computer programs: CAD-4 EXPRESS, NRCVAX DATRD2, NRCVAX SOLVER, NRCVAX LSTSQ, NRCVAX ORTEP, NRCVAX TABLES.

Selected geometric parameters (Å, º) top
P—O11.5932 (16)C7—C81.406 (3)
P—O21.4641 (15)C7—C121.390 (3)
P—C11.779 (2)C8—C91.376 (3)
P—C131.790 (2)C9—C101.381 (4)
O1—C121.387 (2)C10—C111.371 (3)
O3—C141.370 (3)C11—C121.379 (3)
O3—C191.412 (3)C13—C141.396 (3)
O4—C171.363 (3)C13—C181.396 (3)
O4—C221.389 (4)C14—C151.384 (3)
O5—C201.381 (3)C15—C161.369 (4)
O5—C211.437 (4)C16—C171.375 (4)
O6—C231.415 (4)C17—C181.382 (3)
O6—C241.447 (6)C19—C201.494 (4)
O6—C23'1.380 (7)C20—C211.399 (4)
O6—C24'1.395 (7)C22—C231.541 (5)
C1—C21.395 (3)C22—C23'1.520 (7)
C1—C61.406 (3)C23—C241.415 (6)
C2—C31.376 (3)C23—C23'0.776 (8)
C3—C41.375 (4)C23—C24'0.910 (7)
C4—C51.377 (3)C24—C23'1.008 (8)
C5—C61.395 (3)C24—C24'1.455 (8)
C6—C71.478 (3)C23'—C24'1.436 (9)
O1—P—O2111.96 (9)O4—C17—C16115.3 (2)
O1—P—C1103.87 (9)O4—C17—C18125.2 (2)
O1—P—C13104.14 (9)C16—C17—C18119.5 (2)
O2—P—C1115.46 (9)C13—C18—C17120.0 (2)
O2—P—C13112.41 (9)O3—C19—C20108.1 (2)
C1—P—C13108.07 (10)O5—C20—C19116.8 (3)
P—O1—C12127.02 (13)O5—C20—C2162.3 (2)
C14—O3—C19118.50 (18)C19—C20—C21123.4 (3)
C17—O4—C22119.2 (2)O5—C21—C2058.26 (19)
C20—O5—C2159.49 (19)O4—C22—C2398.6 (3)
C23—O6—C2459.3 (3)O4—C22—C23'124.6 (3)
C23—O6—C23'32.2 (3)C23—C22—C23'29.3 (3)
C23—O6—C24'37.8 (3)O6—C23—C22114.2 (3)
C24—O6—C23'41.7 (3)O6—C23—C2461.5 (3)
C24—O6—C24'61.5 (4)O6—C23—C23'71.4 (6)
C23'—O6—C24'62.3 (4)O6—C23—C24'69.9 (5)
P—C1—C2117.50 (16)C22—C23—C24116.7 (4)
P—C1—C6122.00 (15)C22—C23—C23'73.9 (6)
C2—C1—C6120.51 (19)C22—C23—C24'169.4 (6)
C1—C2—C3120.4 (2)C24—C23—C23'43.7 (6)
C2—C3—C4119.6 (2)C24—C23—C24'73.9 (5)
C3—C4—C5120.8 (2)C23'—C23—C24'116.6 (8)
C4—C5—C6121.2 (2)O6—C24—C2359.2 (3)
C1—C6—C5117.53 (18)O6—C24—C23'65.6 (5)
C1—C6—C7120.62 (18)O6—C24—C24'57.5 (3)
C5—C6—C7121.81 (18)C23—C24—C23'32.1 (4)
C6—C7—C8121.96 (18)C23—C24—C24'37.0 (3)
C6—C7—C12122.35 (17)C23'—C24—C24'68.6 (5)
C8—C7—C12115.67 (18)O6—C23'—C22117.7 (5)
C7—C8—C9121.7 (2)O6—C23'—C2376.4 (6)
C8—C9—C10120.4 (2)O6—C23'—C2472.7 (5)
C9—C10—C11119.6 (2)O6—C23'—C24'59.4 (4)
C10—C11—C12119.6 (2)C22—C23'—C2376.8 (6)
O1—C12—C7122.51 (17)C22—C23'—C24169.2 (8)
O1—C12—C11114.45 (18)C22—C23'—C24'111.3 (5)
C7—C12—C11123.02 (18)C23—C23'—C24104.3 (8)
P—C13—C14122.03 (16)C23—C23'—C24'34.5 (5)
P—C13—C18118.26 (16)C24—C23'—C24'70.6 (6)
C14—C13—C18119.64 (19)O6—C24'—C2372.3 (5)
O3—C14—C13116.71 (19)O6—C24'—C2461.0 (4)
O3—C14—C15123.9 (2)O6—C24'—C23'58.3 (4)
C13—C14—C15119.4 (2)C23—C24'—C2469.2 (5)
C14—C15—C16120.2 (2)C23—C24'—C23'28.9 (4)
C15—C16—C17121.2 (2)C24—C24'—C23'40.8 (4)
 

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