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organic papers

o1456

Andreas Deckenet al. C14H9O2P DOI: 10.1107/S1600536804018616 Acta Cryst.(2004). E60, o1456±o1457 Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

2-Phenylisophosphindoline-1,3-dione

Andreas Decken,* Erin D. Gill and Frank Bottomley

Department of Chemistry, University of New Brunswick, Fredericton, NB, PO Box 45222, Canada E3B 6E2

Correspondence e-mail: adecken@unb.ca

Key indicators Single-crystal X-ray study T= 173 K

Mean(C±C) = 0.003 AÊ Rfactor = 0.032 wRfactor = 0.091

Data-to-parameter ratio = 10.4

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, C14H9O2P, displays a near-planar

iso-phosphindoline-1,3-dione skeleton with slightly displaced P and O atoms. Weak CÐH O hydrogen bonding in the crystal structure results in a three-dimensional network.

Comment

The title compound, (I), is a rare example of a crystal-lographically characterized dicarbonylphosphine. The only related compound whose crystal structure has been reported is bis(2,2-dimethylpropionyl)phenylphosphine, [tBuC(O)]

2P±Ph,

(II) (Beckeret al., 1985).

The isophosphindoline-1,3-dione skeleton in (I) is almost planar, in contrast to compound (II), where rotation around the PÐC bonds results in an almost orthogonal orientation of the two carbonyl groups with an OÐC CÐO angle of 73.49

[no standard uncertainty available (Becker et al., 1985)]. In compound (I), the P and O atoms deviate by ÿ0.388 (2), 0.209 (3) and 0.204 (2) AÊ from the C1/C3/C3A/C7A plane, most likely because of the steric demand of the phenyl group. In the absence of the phenyl group, as is the case in the isophosphindolyl-1,3-dione anion (Liotta et al., 1984), planarity of the same molecular fragment is observed. The geometry at the P atom is trigonal±pyramidal in compound (I), indicating a stereochemically active electron pair. This is in contrast to the nitrogen analogue of (I) (Magomedovaet al., 1981), where the N atom is in a trigonal±planar environment. In the crystal lattice, 2-phenylisophosphindoline-1,3-dione

Received 21 July 2004 Accepted 29 July 2004 Online 7 August 2004

Figure 1

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employs both carbonyl O atoms for CÐH O hydrogen bonding (see Table 1), resulting in a three-dimensional network.

Experimental

The title compound was prepared according to a published procedure (Fenskeet al., 1976).

Crystal data

C14H9O2P

Mr= 240.18 Monoclinic,P21=n

a= 9.4273 (15) AÊ

b= 14.479 (2) AÊ

c= 9.4762 (15) AÊ

= 117.662 (2)

V= 1145.7 (3) AÊ3

Z= 4

Dx= 1.393 Mg mÿ3 MoKradiation Cell parameters from 3469

re¯ections

= 2.5±25.9

= 0.22 mmÿ1

T= 173 (2) K Plate, yellow

0.400.300.05 mm

Data collection

Bruker SMART 1000/P4 diffractometer

!and'scans

Absorption correction: none 5722 measured re¯ections 1970 independent re¯ections

1736 re¯ections withI> 2(I)

Rint= 0.021

max= 25.0

h=ÿ11!10

k=ÿ16!17

l=ÿ10!11

Re®nement

Re®nement onF2

R[F2> 2(F2)] = 0.032

wR(F2) = 0.091

S= 1.07 1970 re¯ections 190 parameters

All H-atom parameters re®ned

w= 1/[2(F

o2) + (0.0543P)2 + 0.297P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.37 e AÊÿ3

min=ÿ0.16 e AÊÿ3

Table 1

Hydrogen-bonding geometry (AÊ,).

DÐH A DÐH H A D A DÐH A

C4ÐH4 O2i 0.96 (2) 2.59 (2) 3.517 (2) 163.5 (14)

C7ÐH7 O2ii 0.91 (2) 2.37 (2) 3.201 (2) 150.5 (17)

C10ÐH10 O1iii 0.90 (2) 2.53 (2) 3.368 (2) 155.5 (16)

Symmetry codes: (i) 1ÿx;ÿy;ÿz; (ii)3

2ÿx;12‡y;12ÿz; (iii)52ÿx;yÿ12;12ÿz.

H atoms were found in difference Fourier maps and re®ned with isotropic displacement parameters. The ®nal CÐH distances are in the range 0.91 (2)±0.96 (2) AÊ.

Data collection: SMART (Bruker, 1997±1999); cell re®nement:

SMART; data reduction: SAINT(Bruker, 1997±1999); program(s) used to solve structure:SHELXS97 (Sheldrick, 1997a); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997a); molecular graphics:SHELXTL (Sheldrick, 1997b); software used to prepare material for publication:SHELXTL.

This work was supported by the Natural Sciences and Engineering Research Council of Canada.

References

Becker, G., Becker, B., Birkhahn, M., Mundt, O. & Schmidt, R. E. (1985).Z. Anorg. Allg. Chem.529, 97±110.

Bruker (1997±1999).SMARTandSAINT.Versions 5.059. Bruker AXS Inc., Madison, Wisconsin, USA.

Fenske, D., Langer, E., Heymann, M. & Becher, H. J. (1976).Chem. Ber.109, 359±362.

Liotta, C. L., McLaughlin, M. L., VanDerveer, D. G. & O'Brian, B. A. (1984).

Tetrahedron Lett.25, 1665±1668.

Magomedova, N. S., Neigauz, M. G., Zavodnik, V. E. & Bel'skii, V. K. (1981).

Kristallogra®ya(Crystallogr. Rep.),26, 841±844.

Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

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supporting information

sup-1

Acta Cryst. (2004). E60, o1456–o1457

supporting information

Acta Cryst. (2004). E60, o1456–o1457 [https://doi.org/10.1107/S1600536804018616]

2-Phenylisophosphindoline-1,3-dione

Andreas Decken, Erin D. Gill and Frank Bottomley

2H-2-Phenylisophosphindoline-1,3-dione

Crystal data

C14H9O2P Mr = 240.18

Monoclinic, P21/n Hall symbol: -P 2yn a = 9.4273 (15) Å b = 14.479 (2) Å c = 9.4762 (15) Å β = 117.662 (2)° V = 1145.7 (3) Å3 Z = 4

F(000) = 496 Dx = 1.393 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3469 reflections θ = 2.5–25.9°

µ = 0.22 mm−1 T = 173 K Plate, yellow

0.40 × 0.30 × 0.05 mm

Data collection

Bruker SMART1000/P4 diffractometer

Radiation source: fine-focus sealed tube, Bruker SMART1000/P4

Graphite monochromator ω and φ scans

5722 measured reflections

1970 independent reflections 1736 reflections with I > 2σ(I) Rint = 0.021

θmax = 25.0°, θmin = 2.5° h = −11→10

k = −16→17 l = −10→11

Refinement

Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.032 wR(F2) = 0.091 S = 1.07 1970 reflections 190 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

All H-atom parameters refined w = 1/[σ2(F

o2) + (0.0543P)2 + 0.297P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.37 e Å−3 Δρmin = −0.16 e Å−3

Special details

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

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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)

x y z Uiso*/Ueq

P 0.91945 (5) 0.15848 (3) 0.09908 (5) 0.03064 (16) C1 0.9097 (2) 0.25440 (10) 0.22354 (19) 0.0330 (4) O1 1.01436 (15) 0.30984 (8) 0.29308 (16) 0.0482 (3) C3 0.74442 (17) 0.10542 (10) 0.10761 (17) 0.0269 (3) O2 0.70197 (13) 0.02661 (7) 0.07410 (13) 0.0346 (3) C3A 0.66489 (18) 0.17416 (10) 0.16144 (17) 0.0272 (3) C4 0.5172 (2) 0.16283 (12) 0.1561 (2) 0.0357 (4) C5 0.4577 (2) 0.23381 (14) 0.2087 (2) 0.0450 (5) C6 0.5437 (2) 0.31423 (13) 0.2661 (2) 0.0444 (5) C7 0.6911 (2) 0.32518 (12) 0.2742 (2) 0.0386 (4) C7A 0.75202 (19) 0.25407 (10) 0.22099 (17) 0.0294 (4) C8 1.07845 (18) 0.08597 (11) 0.24142 (18) 0.0308 (4) C9 1.17345 (18) 0.03958 (11) 0.1895 (2) 0.0335 (4) C10 1.2884 (2) −0.02132 (12) 0.2878 (2) 0.0404 (4) C11 1.3100 (2) −0.03584 (13) 0.4392 (2) 0.0428 (4) C12 1.2184 (2) 0.01108 (14) 0.4935 (2) 0.0458 (5) C13 1.1030 (2) 0.07134 (13) 0.3954 (2) 0.0404 (4) H4 0.458 (2) 0.1072 (14) 0.114 (2) 0.048 (5)* H5 0.360 (3) 0.2253 (14) 0.206 (2) 0.055 (6)* H6 0.499 (2) 0.3591 (14) 0.300 (2) 0.050 (5)* H7 0.753 (2) 0.3770 (14) 0.311 (2) 0.051 (6)* H9 1.156 (2) 0.0487 (12) 0.085 (3) 0.040 (5)* H10 1.349 (2) −0.0514 (13) 0.252 (2) 0.042 (5)* H11 1.387 (2) −0.0788 (14) 0.507 (2) 0.047 (5)* H12 1.232 (3) 0.0016 (14) 0.598 (3) 0.060 (6)* H13 1.040 (2) 0.1021 (14) 0.432 (2) 0.048 (5)*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

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supporting information

sup-3

Acta Cryst. (2004). E60, o1456–o1457

C7A 0.0365 (9) 0.0253 (7) 0.0242 (8) 0.0015 (6) 0.0124 (7) 0.0016 (6) C8 0.0270 (8) 0.0333 (8) 0.0316 (8) −0.0034 (6) 0.0131 (7) −0.0031 (6) C9 0.0280 (8) 0.0391 (9) 0.0333 (9) −0.0047 (7) 0.0142 (7) −0.0062 (7) C10 0.0301 (9) 0.0444 (10) 0.0449 (10) 0.0011 (7) 0.0160 (8) −0.0080 (8) C11 0.0308 (9) 0.0447 (10) 0.0421 (10) 0.0010 (8) 0.0077 (8) 0.0014 (8) C12 0.0421 (11) 0.0577 (11) 0.0331 (9) 0.0029 (9) 0.0138 (8) 0.0048 (8) C13 0.0378 (9) 0.0529 (11) 0.0329 (9) 0.0054 (8) 0.0184 (8) 0.0006 (8)

Geometric parameters (Å, º)

P—C8 1.8142 (16) C6—H6 0.91 (2) P—C1 1.8517 (16) C7—C7A 1.383 (2) P—C3 1.8556 (15) C7—H7 0.92 (2) C1—O1 1.2033 (19) C8—C9 1.380 (2) C1—C7A 1.476 (2) C8—C13 1.383 (2) C3—O2 1.2021 (18) C9—C10 1.372 (2) C3—C3A 1.473 (2) C9—H9 0.94 (2) C3A—C7A 1.379 (2) C10—C11 1.369 (3) C3A—C4 1.380 (2) C10—H10 0.90 (2) C4—C5 1.370 (2) C11—C12 1.373 (3) C4—H4 0.96 (2) C11—H11 0.95 (2) C5—C6 1.378 (3) C12—C13 1.368 (3) C5—H5 0.91 (2) C12—H12 0.94 (2) C6—C7 1.365 (3) C13—H13 0.928 (19)

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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

C4—H4···O2i 0.96 (2) 2.59 (2) 3.517 (2) 163.5 (14) C7—H7···O2ii 0.91 (2) 2.37 (2) 3.201 (2) 150.5 (17) C10—H10···O1iii 0.90 (2) 2.53 (2) 3.368 (2) 155.5 (16)

References

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