The title compound, C
14H
9O
2P, 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
CCDC reference: 251629
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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.
2
H-2-Phenylisophosphindoline-1,3-dione
top
Crystal data top
C14H9O2P | F(000) = 496 |
Mr = 240.18 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3469 reflections |
a = 9.4273 (15) Å | θ = 2.5–25.9° |
b = 14.479 (2) Å | µ = 0.22 mm−1 |
c = 9.4762 (15) Å | T = 173 K |
β = 117.662 (2)° | Plate, yellow |
V = 1145.7 (3) Å3 | 0.40 × 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/P4 | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
ω and φ scans | h = −11→10 |
5722 measured reflections | k = −16→17 |
1970 independent reflections | l = −10→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | All 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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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 | 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) top | U11 | U22 | U33 | U12 | U13 | U23 |
P | 0.0329 (3) | 0.0317 (3) | 0.0300 (3) | −0.00078 (16) | 0.01689 (19) | −0.00048 (15) |
C1 | 0.0409 (9) | 0.0252 (8) | 0.0321 (8) | −0.0051 (7) | 0.0164 (7) | 0.0008 (6) |
O1 | 0.0499 (8) | 0.0396 (7) | 0.0539 (8) | −0.0201 (6) | 0.0230 (7) | −0.0107 (6) |
C3 | 0.0281 (8) | 0.0253 (8) | 0.0230 (7) | 0.0019 (6) | 0.0083 (6) | 0.0019 (6) |
O2 | 0.0372 (6) | 0.0222 (6) | 0.0397 (6) | −0.0008 (4) | 0.0139 (5) | −0.0028 (4) |
C3A | 0.0313 (8) | 0.0254 (7) | 0.0235 (7) | 0.0022 (6) | 0.0114 (6) | 0.0019 (6) |
C4 | 0.0312 (9) | 0.0381 (9) | 0.0360 (9) | 0.0006 (7) | 0.0142 (7) | 0.0000 (7) |
C5 | 0.0364 (10) | 0.0575 (12) | 0.0443 (10) | 0.0083 (9) | 0.0213 (9) | −0.0002 (9) |
C6 | 0.0513 (11) | 0.0459 (10) | 0.0368 (10) | 0.0184 (9) | 0.0212 (9) | −0.0021 (8) |
C7 | 0.0522 (11) | 0.0281 (8) | 0.0310 (9) | 0.0050 (8) | 0.0154 (8) | −0.0033 (7) |
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) top
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) |
| | | |
C8—P—C1 | 103.21 (7) | C7A—C7—H7 | 116.7 (13) |
C8—P—C3 | 99.93 (7) | C3A—C7A—C7 | 120.29 (15) |
C1—P—C3 | 88.56 (7) | C3A—C7A—C1 | 114.43 (13) |
O1—C1—C7A | 125.08 (15) | C7—C7A—C1 | 125.27 (15) |
O1—C1—P | 125.36 (13) | C9—C8—C13 | 118.90 (15) |
C7A—C1—P | 109.54 (10) | C9—C8—P | 117.73 (12) |
O2—C3—C3A | 124.93 (14) | C13—C8—P | 123.27 (12) |
O2—C3—P | 125.12 (12) | C10—C9—C8 | 120.62 (16) |
C3A—C3—P | 109.95 (10) | C10—C9—H9 | 120.3 (11) |
C7A—C3A—C4 | 120.94 (14) | C8—C9—H9 | 119.1 (11) |
C7A—C3A—C3 | 113.99 (13) | C11—C10—C9 | 119.79 (17) |
C4—C3A—C3 | 125.07 (14) | C11—C10—H10 | 120.8 (12) |
C5—C4—C3A | 118.28 (17) | C9—C10—H10 | 119.4 (12) |
C5—C4—H4 | 122.0 (12) | C10—C11—C12 | 120.22 (18) |
C3A—C4—H4 | 119.7 (11) | C10—C11—H11 | 120.4 (11) |
C4—C5—C6 | 120.82 (18) | C12—C11—H11 | 119.4 (11) |
C4—C5—H5 | 117.5 (14) | C13—C12—C11 | 120.11 (18) |
C6—C5—H5 | 121.6 (13) | C13—C12—H12 | 118.7 (13) |
C7—C6—C5 | 121.15 (16) | C11—C12—H12 | 121.2 (13) |
C7—C6—H6 | 121.7 (12) | C12—C13—C8 | 120.35 (17) |
C5—C6—H6 | 117.1 (12) | C12—C13—H13 | 119.8 (12) |
C6—C7—C7A | 118.51 (17) | C8—C13—H13 | 119.9 (12) |
C6—C7—H7 | 124.8 (12) | | |
Hydrogen-bond geometry (Å, º) top
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) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+5/2, y−1/2, −z+1/2. |