Download citation
Download citation
link to html
The title compound, C14H9O2P, displays a near-planar iso­phos­phindoline-1,3-dione skeleton with slightly displaced P and O atoms. Weak C—H...O hydrogen bonding in the crystal structure results in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018616/lh6252sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018616/lh6252Isup2.hkl
Contains datablock I

CCDC reference: 251629

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.091
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.26 PLAT322_ALERT_2_C Check Hybridisation of P in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1997-1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2H-2-Phenylisophosphindoline-1,3-dione top
Crystal data top
C14H9O2PF(000) = 496
Mr = 240.18Dx = 1.393 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3469 reflections
a = 9.4273 (15) Åθ = 2.5–25.9°
b = 14.479 (2) ŵ = 0.22 mm1
c = 9.4762 (15) ÅT = 173 K
β = 117.662 (2)°Plate, yellow
V = 1145.7 (3) Å30.40 × 0.30 × 0.05 mm
Z = 4
Data collection top
Bruker SMART1000/P4
diffractometer
1736 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Bruker SMART1000/P4Rint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω and φ scansh = 1110
5722 measured reflectionsk = 1617
1970 independent reflectionsl = 1011
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.297P]
where P = (Fo2 + 2Fc2)/3
1970 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

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

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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) top
xyzUiso*/Ueq
P0.91945 (5)0.15848 (3)0.09908 (5)0.03064 (16)
C10.9097 (2)0.25440 (10)0.22354 (19)0.0330 (4)
O11.01436 (15)0.30984 (8)0.29308 (16)0.0482 (3)
C30.74442 (17)0.10542 (10)0.10761 (17)0.0269 (3)
O20.70197 (13)0.02661 (7)0.07410 (13)0.0346 (3)
C3A0.66489 (18)0.17416 (10)0.16144 (17)0.0272 (3)
C40.5172 (2)0.16283 (12)0.1561 (2)0.0357 (4)
C50.4577 (2)0.23381 (14)0.2087 (2)0.0450 (5)
C60.5437 (2)0.31423 (13)0.2661 (2)0.0444 (5)
C70.6911 (2)0.32518 (12)0.2742 (2)0.0386 (4)
C7A0.75202 (19)0.25407 (10)0.22099 (17)0.0294 (4)
C81.07845 (18)0.08597 (11)0.24142 (18)0.0308 (4)
C91.17345 (18)0.03958 (11)0.1895 (2)0.0335 (4)
C101.2884 (2)0.02132 (12)0.2878 (2)0.0404 (4)
C111.3100 (2)0.03584 (13)0.4392 (2)0.0428 (4)
C121.2184 (2)0.01108 (14)0.4935 (2)0.0458 (5)
C131.1030 (2)0.07134 (13)0.3954 (2)0.0404 (4)
H40.458 (2)0.1072 (14)0.114 (2)0.048 (5)*
H50.360 (3)0.2253 (14)0.206 (2)0.055 (6)*
H60.499 (2)0.3591 (14)0.300 (2)0.050 (5)*
H70.753 (2)0.3770 (14)0.311 (2)0.051 (6)*
H91.156 (2)0.0487 (12)0.085 (3)0.040 (5)*
H101.349 (2)0.0514 (13)0.252 (2)0.042 (5)*
H111.387 (2)0.0788 (14)0.507 (2)0.047 (5)*
H121.232 (3)0.0016 (14)0.598 (3)0.060 (6)*
H131.040 (2)0.1021 (14)0.432 (2)0.048 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0329 (3)0.0317 (3)0.0300 (3)0.00078 (16)0.01689 (19)0.00048 (15)
C10.0409 (9)0.0252 (8)0.0321 (8)0.0051 (7)0.0164 (7)0.0008 (6)
O10.0499 (8)0.0396 (7)0.0539 (8)0.0201 (6)0.0230 (7)0.0107 (6)
C30.0281 (8)0.0253 (8)0.0230 (7)0.0019 (6)0.0083 (6)0.0019 (6)
O20.0372 (6)0.0222 (6)0.0397 (6)0.0008 (4)0.0139 (5)0.0028 (4)
C3A0.0313 (8)0.0254 (7)0.0235 (7)0.0022 (6)0.0114 (6)0.0019 (6)
C40.0312 (9)0.0381 (9)0.0360 (9)0.0006 (7)0.0142 (7)0.0000 (7)
C50.0364 (10)0.0575 (12)0.0443 (10)0.0083 (9)0.0213 (9)0.0002 (9)
C60.0513 (11)0.0459 (10)0.0368 (10)0.0184 (9)0.0212 (9)0.0021 (8)
C70.0522 (11)0.0281 (8)0.0310 (9)0.0050 (8)0.0154 (8)0.0033 (7)
C7A0.0365 (9)0.0253 (7)0.0242 (8)0.0015 (6)0.0124 (7)0.0016 (6)
C80.0270 (8)0.0333 (8)0.0316 (8)0.0034 (6)0.0131 (7)0.0031 (6)
C90.0280 (8)0.0391 (9)0.0333 (9)0.0047 (7)0.0142 (7)0.0062 (7)
C100.0301 (9)0.0444 (10)0.0449 (10)0.0011 (7)0.0160 (8)0.0080 (8)
C110.0308 (9)0.0447 (10)0.0421 (10)0.0010 (8)0.0077 (8)0.0014 (8)
C120.0421 (11)0.0577 (11)0.0331 (9)0.0029 (9)0.0138 (8)0.0048 (8)
C130.0378 (9)0.0529 (11)0.0329 (9)0.0054 (8)0.0184 (8)0.0006 (8)
Geometric parameters (Å, º) top
P—C81.8142 (16)C6—H60.91 (2)
P—C11.8517 (16)C7—C7A1.383 (2)
P—C31.8556 (15)C7—H70.92 (2)
C1—O11.2033 (19)C8—C91.380 (2)
C1—C7A1.476 (2)C8—C131.383 (2)
C3—O21.2021 (18)C9—C101.372 (2)
C3—C3A1.473 (2)C9—H90.94 (2)
C3A—C7A1.379 (2)C10—C111.369 (3)
C3A—C41.380 (2)C10—H100.90 (2)
C4—C51.370 (2)C11—C121.373 (3)
C4—H40.96 (2)C11—H110.95 (2)
C5—C61.378 (3)C12—C131.368 (3)
C5—H50.91 (2)C12—H120.94 (2)
C6—C71.365 (3)C13—H130.928 (19)
C8—P—C1103.21 (7)C7A—C7—H7116.7 (13)
C8—P—C399.93 (7)C3A—C7A—C7120.29 (15)
C1—P—C388.56 (7)C3A—C7A—C1114.43 (13)
O1—C1—C7A125.08 (15)C7—C7A—C1125.27 (15)
O1—C1—P125.36 (13)C9—C8—C13118.90 (15)
C7A—C1—P109.54 (10)C9—C8—P117.73 (12)
O2—C3—C3A124.93 (14)C13—C8—P123.27 (12)
O2—C3—P125.12 (12)C10—C9—C8120.62 (16)
C3A—C3—P109.95 (10)C10—C9—H9120.3 (11)
C7A—C3A—C4120.94 (14)C8—C9—H9119.1 (11)
C7A—C3A—C3113.99 (13)C11—C10—C9119.79 (17)
C4—C3A—C3125.07 (14)C11—C10—H10120.8 (12)
C5—C4—C3A118.28 (17)C9—C10—H10119.4 (12)
C5—C4—H4122.0 (12)C10—C11—C12120.22 (18)
C3A—C4—H4119.7 (11)C10—C11—H11120.4 (11)
C4—C5—C6120.82 (18)C12—C11—H11119.4 (11)
C4—C5—H5117.5 (14)C13—C12—C11120.11 (18)
C6—C5—H5121.6 (13)C13—C12—H12118.7 (13)
C7—C6—C5121.15 (16)C11—C12—H12121.2 (13)
C7—C6—H6121.7 (12)C12—C13—C8120.35 (17)
C5—C6—H6117.1 (12)C12—C13—H13119.8 (12)
C6—C7—C7A118.51 (17)C8—C13—H13119.9 (12)
C6—C7—H7124.8 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.96 (2)2.59 (2)3.517 (2)163.5 (14)
C7—H7···O2ii0.91 (2)2.37 (2)3.201 (2)150.5 (17)
C10—H10···O1iii0.90 (2)2.53 (2)3.368 (2)155.5 (16)
Symmetry codes: (i) x+1, y, z; (ii) x+3/2, y+1/2, z+1/2; (iii) x+5/2, y1/2, z+1/2.
 

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