Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047356/tk2197sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047356/tk2197Isup2.hkl |
CCDC reference: 663851
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.121
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 6
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 23.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 6.38 Deg. C5B -P1 -C5A 1.555 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For background, see: Mason (1961); Elding-Pontén (1993). For reference structural data, see: Allen et al. (1987).
Triphenylphosphine oxide and succinimide were mixed in a 1:1 ratio in acetonitrile. Colourless blocks of (I) grew as the solvent slowly evaporated.
One of the ppo phenyl rings is disordered over two positions in a 0.551 (15):0.449 (15) ratio. The two rings were modelled as regular hexagons with C—C = 1.39 Å and Uiso values were refined for the C atoms.
The hydrogen atoms were geometrically placed (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).
In the title 1:1 adduct, C18H15OP·C4H5NO2, (I), the component species interact by an almost linear N—H···O hydrogen bond (Table 1). The five-membered ring of the succinimide (suc) molecule in (I) is close to flat (r.m.s. deviation = 0.006 Å), similar to that in other suc-containing adducts (Elding-Pontén, 1993), whereas in succinimide itself (Mason, 1961), the ring is slightly puckered. One of the phenyl rings in the triphenylphosphine oxide (ppo) molecule in (I) is disordered over two positions, otherwise the geometric parameters for (I) may be regarded as normal (Allen et al., 1987). It is notable that although O1 accepts three of these putative bonds, and O2 none, the C1=O1 and C4=O2 bond lengths are identical.
Some weak C—H···O interactions (Table 1) from ppo to sac help establish the packing in (I). Aromatic π-π stacking interactions in (I) are negligible, as the minimum aromatic ring centroid···centroid separation is greater than 4.1 Å.
For background, see: Mason (1961); Elding-Pontén (1993). For reference structural data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C18H15OP·C4H5NO2 | F(000) = 1584 |
Mr = 377.36 | Dx = 1.269 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5293 reflections |
a = 8.5825 (4) Å | θ = 2.4–24.8° |
b = 17.2754 (7) Å | µ = 0.16 mm−1 |
c = 26.6505 (11) Å | T = 293 K |
V = 3951.4 (3) Å3 | Chunk, colourless |
Z = 8 | 0.42 × 0.35 × 0.18 mm |
Bruker SMART 1000 CCD diffractometer | 2454 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −10→10 |
26415 measured reflections | k = −20→21 |
3887 independent reflections | l = −28→32 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0616P)2 + 0.24P] where P = (Fo2 + 2Fc2)/3 |
3887 reflections | (Δ/σ)max = 0.001 |
209 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C18H15OP·C4H5NO2 | V = 3951.4 (3) Å3 |
Mr = 377.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.5825 (4) Å | µ = 0.16 mm−1 |
b = 17.2754 (7) Å | T = 293 K |
c = 26.6505 (11) Å | 0.42 × 0.35 × 0.18 mm |
Bruker SMART 1000 CCD diffractometer | 2454 reflections with I > 2σ(I) |
26415 measured reflections | Rint = 0.047 |
3887 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.32 e Å−3 |
3887 reflections | Δρmin = −0.30 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.1713 (3) | 0.41653 (15) | 0.31308 (10) | 0.0576 (6) | |
C2 | 0.0888 (4) | 0.45266 (16) | 0.26964 (12) | 0.0853 (9) | |
H2A | −0.0221 | 0.4565 | 0.2762 | 0.102* | |
H2B | 0.1042 | 0.4223 | 0.2394 | 0.102* | |
C3 | 0.1599 (4) | 0.53217 (16) | 0.26394 (11) | 0.0822 (9) | |
H3A | 0.2056 | 0.5383 | 0.2309 | 0.099* | |
H3B | 0.0818 | 0.5721 | 0.2688 | 0.099* | |
C4 | 0.2834 (3) | 0.53676 (15) | 0.30405 (9) | 0.0570 (6) | |
N1 | 0.2801 (2) | 0.46846 (11) | 0.32998 (7) | 0.0527 (5) | |
H1 | 0.3412 | 0.4589 | 0.3548 | 0.063* | |
O1 | 0.1478 (2) | 0.35331 (11) | 0.33060 (8) | 0.0800 (6) | |
O2 | 0.3707 (2) | 0.59001 (11) | 0.31185 (7) | 0.0800 (6) | |
P1 | 0.61012 (6) | 0.39626 (3) | 0.42066 (2) | 0.04155 (17) | |
O3 | 0.45860 (17) | 0.43822 (9) | 0.41661 (5) | 0.0551 (4) | |
C5A | 0.7853 (5) | 0.4593 (2) | 0.42092 (16) | 0.0400 (19)* | 0.449 (15) |
C6A | 0.7718 (6) | 0.5331 (2) | 0.4007 (2) | 0.0610 (18)* | 0.449 (15) |
H6A | 0.6764 | 0.5500 | 0.3883 | 0.073* | 0.449 (15) |
C7A | 0.9008 (8) | 0.58172 (19) | 0.3991 (3) | 0.063 (2)* | 0.449 (15) |
H7A | 0.8917 | 0.6311 | 0.3856 | 0.075* | 0.449 (15) |
C8A | 1.0433 (7) | 0.5564 (3) | 0.4177 (2) | 0.0610 (19)* | 0.449 (15) |
H8A | 1.1296 | 0.5890 | 0.4166 | 0.073* | 0.449 (15) |
C9A | 1.0567 (5) | 0.4826 (4) | 0.43792 (17) | 0.0604 (19)* | 0.449 (15) |
H9A | 1.1521 | 0.4657 | 0.4504 | 0.073* | 0.449 (15) |
C10A | 0.9278 (5) | 0.4340 (3) | 0.43953 (15) | 0.0556 (18)* | 0.449 (15) |
H10A | 0.9368 | 0.3846 | 0.4531 | 0.067* | 0.449 (15) |
C5B | 0.7646 (4) | 0.46322 (11) | 0.41665 (8) | 0.0463 (18)* | 0.551 (15) |
C6B | 0.7367 (6) | 0.53136 (14) | 0.39039 (13) | 0.0577 (15)* | 0.551 (15) |
H6B | 0.6396 | 0.5402 | 0.3761 | 0.069* | 0.551 (15) |
C7B | 0.8542 (7) | 0.58627 (15) | 0.38555 (17) | 0.0728 (17)* | 0.551 (15) |
H7B | 0.8356 | 0.6319 | 0.3680 | 0.087* | 0.551 (15) |
C8B | 0.9994 (7) | 0.5730 (2) | 0.40696 (16) | 0.0628 (16)* | 0.551 (15) |
H8B | 1.0780 | 0.6098 | 0.4037 | 0.075* | 0.551 (15) |
C9B | 1.0273 (5) | 0.5049 (3) | 0.43322 (14) | 0.0627 (15)* | 0.551 (15) |
H9B | 1.1245 | 0.4960 | 0.4475 | 0.075* | 0.551 (15) |
C10B | 0.9098 (3) | 0.4500 (2) | 0.43806 (10) | 0.0510 (14)* | 0.551 (15) |
H10B | 0.9285 | 0.4044 | 0.4556 | 0.061* | 0.551 (15) |
C11 | 0.62595 (19) | 0.34155 (8) | 0.47816 (6) | 0.0412 (5) | |
C12 | 0.5739 (2) | 0.37552 (10) | 0.52185 (6) | 0.0600 (6) | |
H12 | 0.5329 | 0.4253 | 0.5211 | 0.072* | |
C13 | 0.5825 (3) | 0.33567 (18) | 0.56671 (10) | 0.0728 (8) | |
H13 | 0.5467 | 0.3587 | 0.5961 | 0.087* | |
C14 | 0.6426 (3) | 0.2632 (2) | 0.56810 (12) | 0.0757 (9) | |
H14 | 0.6472 | 0.2365 | 0.5984 | 0.091* | |
C15 | 0.6966 (3) | 0.22924 (16) | 0.52530 (13) | 0.0800 (9) | |
H15 | 0.7388 | 0.1797 | 0.5265 | 0.096* | |
C16 | 0.6886 (3) | 0.26835 (14) | 0.48007 (10) | 0.0628 (7) | |
H16 | 0.7255 | 0.2451 | 0.4509 | 0.075* | |
C17 | 0.6351 (2) | 0.32944 (12) | 0.36951 (8) | 0.0438 (5) | |
C18 | 0.5031 (3) | 0.29439 (12) | 0.34987 (9) | 0.0503 (6) | |
H18 | 0.4062 | 0.3044 | 0.3641 | 0.060* | |
C19 | 0.5145 (3) | 0.24481 (14) | 0.30941 (10) | 0.0630 (7) | |
H19 | 0.4253 | 0.2216 | 0.2965 | 0.076* | |
C20 | 0.6566 (4) | 0.22971 (16) | 0.28827 (10) | 0.0754 (8) | |
H20 | 0.6636 | 0.1974 | 0.2605 | 0.091* | |
C21 | 0.7882 (4) | 0.26217 (18) | 0.30800 (12) | 0.0871 (9) | |
H21 | 0.8849 | 0.2505 | 0.2942 | 0.105* | |
C22 | 0.7783 (3) | 0.31224 (16) | 0.34827 (10) | 0.0666 (7) | |
H22 | 0.8684 | 0.3346 | 0.3612 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0418 (12) | 0.0676 (16) | 0.0635 (17) | 0.0044 (12) | −0.0009 (12) | 0.0120 (13) |
C2 | 0.090 (2) | 0.0775 (19) | 0.089 (2) | 0.0031 (17) | −0.0414 (17) | 0.0140 (16) |
C3 | 0.102 (2) | 0.0731 (18) | 0.072 (2) | 0.0089 (17) | −0.0285 (17) | 0.0176 (15) |
C4 | 0.0675 (16) | 0.0589 (15) | 0.0445 (14) | 0.0091 (13) | 0.0034 (12) | 0.0048 (12) |
N1 | 0.0472 (11) | 0.0651 (12) | 0.0458 (11) | 0.0052 (10) | −0.0029 (9) | 0.0110 (10) |
O1 | 0.0591 (11) | 0.0782 (13) | 0.1027 (16) | −0.0090 (9) | −0.0085 (10) | 0.0330 (12) |
O2 | 0.1052 (15) | 0.0678 (12) | 0.0669 (13) | −0.0142 (11) | −0.0062 (11) | 0.0062 (10) |
P1 | 0.0431 (3) | 0.0469 (3) | 0.0347 (3) | 0.0038 (3) | −0.0016 (3) | 0.0005 (2) |
O3 | 0.0542 (9) | 0.0655 (10) | 0.0457 (10) | 0.0169 (8) | −0.0036 (8) | 0.0021 (8) |
C11 | 0.0370 (11) | 0.0482 (12) | 0.0385 (12) | −0.0019 (9) | −0.0011 (9) | 0.0019 (9) |
C12 | 0.0745 (17) | 0.0624 (15) | 0.0432 (14) | 0.0115 (13) | −0.0001 (13) | −0.0010 (11) |
C13 | 0.0778 (19) | 0.104 (2) | 0.0369 (15) | 0.0107 (17) | 0.0005 (13) | 0.0069 (14) |
C14 | 0.0561 (16) | 0.107 (2) | 0.0641 (19) | −0.0030 (15) | −0.0027 (14) | 0.0400 (17) |
C15 | 0.081 (2) | 0.0666 (17) | 0.093 (2) | 0.0156 (15) | 0.0052 (18) | 0.0334 (17) |
C16 | 0.0696 (17) | 0.0570 (14) | 0.0617 (16) | 0.0137 (13) | 0.0104 (14) | 0.0102 (12) |
C17 | 0.0444 (12) | 0.0509 (12) | 0.0360 (12) | 0.0001 (10) | 0.0000 (10) | −0.0005 (9) |
C18 | 0.0483 (13) | 0.0511 (13) | 0.0513 (14) | 0.0023 (10) | −0.0059 (11) | 0.0005 (11) |
C19 | 0.0712 (18) | 0.0590 (15) | 0.0588 (16) | −0.0061 (13) | −0.0187 (14) | −0.0060 (12) |
C20 | 0.097 (2) | 0.0779 (19) | 0.0513 (17) | −0.0029 (17) | −0.0004 (16) | −0.0255 (14) |
C21 | 0.0721 (19) | 0.118 (2) | 0.0712 (19) | −0.0092 (18) | 0.0224 (16) | −0.0403 (18) |
C22 | 0.0527 (14) | 0.0897 (19) | 0.0573 (16) | −0.0121 (14) | 0.0087 (13) | −0.0247 (14) |
C1—O1 | 1.205 (3) | C6B—H6B | 0.9300 |
C1—N1 | 1.371 (3) | C7B—C8B | 1.3900 |
C1—C2 | 1.494 (3) | C7B—H7B | 0.9300 |
C2—C3 | 1.511 (4) | C8B—C9B | 1.3900 |
C2—H2A | 0.9700 | C8B—H8B | 0.9300 |
C2—H2B | 0.9700 | C9B—C10B | 1.3900 |
C3—C4 | 1.507 (4) | C9B—H9B | 0.9300 |
C3—H3A | 0.9700 | C10B—H10B | 0.9300 |
C3—H3B | 0.9700 | C11—C16 | 1.375 (3) |
C4—O2 | 1.205 (3) | C11—C12 | 1.3784 |
C4—N1 | 1.368 (3) | C12—C13 | 1.381 (3) |
N1—H1 | 0.8600 | C12—H12 | 0.9300 |
P1—O3 | 1.4928 (15) | C13—C14 | 1.355 (4) |
P1—C5B | 1.763 (2) | C13—H13 | 0.9300 |
P1—C17 | 1.799 (2) | C14—C15 | 1.364 (4) |
P1—C11 | 1.8056 (16) | C14—H14 | 0.9300 |
P1—C5A | 1.856 (3) | C15—C16 | 1.384 (4) |
C5A—C6A | 1.3900 | C15—H15 | 0.9300 |
C5A—C10A | 1.3900 | C16—H16 | 0.9300 |
C6A—C7A | 1.3900 | C17—C22 | 1.386 (3) |
C6A—H6A | 0.9300 | C17—C18 | 1.387 (3) |
C7A—C8A | 1.3900 | C18—C19 | 1.380 (3) |
C7A—H7A | 0.9300 | C18—H18 | 0.9300 |
C8A—C9A | 1.3900 | C19—C20 | 1.369 (4) |
C8A—H8A | 0.9300 | C19—H19 | 0.9300 |
C9A—C10A | 1.3900 | C20—C21 | 1.366 (4) |
C9A—H9A | 0.9300 | C20—H20 | 0.9300 |
C10A—H10A | 0.9300 | C21—C22 | 1.381 (3) |
C5B—C6B | 1.3900 | C21—H21 | 0.9300 |
C5B—C10B | 1.3900 | C22—H22 | 0.9300 |
C6B—C7B | 1.3900 | ||
O1—C1—N1 | 125.4 (2) | C7B—C6B—C5B | 120.0 |
O1—C1—C2 | 126.8 (2) | C7B—C6B—H6B | 120.0 |
N1—C1—C2 | 107.7 (2) | C5B—C6B—H6B | 120.0 |
C1—C2—C3 | 105.4 (2) | C6B—C7B—C8B | 120.0 |
C1—C2—H2A | 110.7 | C6B—C7B—H7B | 120.0 |
C3—C2—H2A | 110.7 | C8B—C7B—H7B | 120.0 |
C1—C2—H2B | 110.7 | C7B—C8B—C9B | 120.0 |
C3—C2—H2B | 110.7 | C7B—C8B—H8B | 120.0 |
H2A—C2—H2B | 108.8 | C9B—C8B—H8B | 120.0 |
C4—C3—C2 | 105.1 (2) | C10B—C9B—C8B | 120.0 |
C4—C3—H3A | 110.7 | C10B—C9B—H9B | 120.0 |
C2—C3—H3A | 110.7 | C8B—C9B—H9B | 120.0 |
C4—C3—H3B | 110.7 | C9B—C10B—C5B | 120.0 |
C2—C3—H3B | 110.7 | C9B—C10B—H10B | 120.0 |
H3A—C3—H3B | 108.8 | C5B—C10B—H10B | 120.0 |
O2—C4—N1 | 125.7 (2) | C16—C11—C12 | 119.14 (16) |
O2—C4—C3 | 126.9 (2) | C16—C11—P1 | 122.84 (15) |
N1—C4—C3 | 107.4 (2) | C12—C11—P1 | 118.02 (9) |
C4—N1—C1 | 114.4 (2) | C11—C12—C13 | 120.11 (18) |
C4—N1—H1 | 122.8 | C11—C12—H12 | 119.9 |
C1—N1—H1 | 122.8 | C13—C12—H12 | 119.9 |
O3—P1—C5B | 109.39 (12) | C14—C13—C12 | 120.3 (3) |
O3—P1—C17 | 111.15 (9) | C14—C13—H13 | 119.9 |
C5B—P1—C17 | 106.59 (9) | C12—C13—H13 | 119.9 |
O3—P1—C11 | 112.40 (8) | C13—C14—C15 | 120.3 (3) |
C5B—P1—C11 | 109.78 (10) | C13—C14—H14 | 119.9 |
C17—P1—C11 | 107.35 (9) | C15—C14—H14 | 119.9 |
O3—P1—C5A | 114.90 (16) | C14—C15—C16 | 120.1 (3) |
C5B—P1—C5A | 6.38 (15) | C14—C15—H15 | 119.9 |
C17—P1—C5A | 106.42 (14) | C16—C15—H15 | 119.9 |
C11—P1—C5A | 104.05 (15) | C11—C16—C15 | 120.1 (2) |
C6A—C5A—C10A | 120.0 | C11—C16—H16 | 120.0 |
C6A—C5A—P1 | 118.0 (2) | C15—C16—H16 | 120.0 |
C10A—C5A—P1 | 122.0 (2) | C22—C17—C18 | 118.5 (2) |
C7A—C6A—C5A | 120.0 | C22—C17—P1 | 123.57 (17) |
C7A—C6A—H6A | 120.0 | C18—C17—P1 | 117.95 (16) |
C5A—C6A—H6A | 120.0 | C19—C18—C17 | 120.5 (2) |
C8A—C7A—C6A | 120.0 | C19—C18—H18 | 119.7 |
C8A—C7A—H7A | 120.0 | C17—C18—H18 | 119.7 |
C6A—C7A—H7A | 120.0 | C20—C19—C18 | 120.2 (2) |
C7A—C8A—C9A | 120.0 | C20—C19—H19 | 119.9 |
C7A—C8A—H8A | 120.0 | C18—C19—H19 | 119.9 |
C9A—C8A—H8A | 120.0 | C21—C20—C19 | 120.0 (2) |
C8A—C9A—C10A | 120.0 | C21—C20—H20 | 120.0 |
C8A—C9A—H9A | 120.0 | C19—C20—H20 | 120.0 |
C10A—C9A—H9A | 120.0 | C20—C21—C22 | 120.4 (3) |
C9A—C10A—C5A | 120.0 | C20—C21—H21 | 119.8 |
C9A—C10A—H10A | 120.0 | C22—C21—H21 | 119.8 |
C5A—C10A—H10A | 120.0 | C21—C22—C17 | 120.4 (2) |
C6B—C5B—C10B | 120.0 | C21—C22—H22 | 119.8 |
C6B—C5B—P1 | 117.20 (7) | C17—C22—H22 | 119.8 |
C10B—C5B—P1 | 122.80 (7) | ||
O1—C1—C2—C3 | 178.8 (3) | C7B—C8B—C9B—C10B | 0.0 |
N1—C1—C2—C3 | −1.1 (3) | C8B—C9B—C10B—C5B | 0.0 |
C1—C2—C3—C4 | 1.3 (3) | C6B—C5B—C10B—C9B | 0.0 |
C2—C3—C4—O2 | 178.1 (3) | P1—C5B—C10B—C9B | 179.49 (9) |
C2—C3—C4—N1 | −1.1 (3) | O3—P1—C11—C16 | 138.65 (18) |
O2—C4—N1—C1 | −178.8 (2) | C5B—P1—C11—C16 | −99.36 (19) |
C3—C4—N1—C1 | 0.4 (3) | C17—P1—C11—C16 | 16.13 (19) |
O1—C1—N1—C4 | −179.4 (2) | C5A—P1—C11—C16 | −96.4 (2) |
C2—C1—N1—C4 | 0.5 (3) | O3—P1—C11—C12 | −41.93 (13) |
O3—P1—C5A—C6A | −21.7 (3) | C5B—P1—C11—C12 | 80.06 (14) |
C5B—P1—C5A—C6A | 9.3 (14) | C17—P1—C11—C12 | −164.45 (12) |
C17—P1—C5A—C6A | 101.7 (3) | C5A—P1—C11—C12 | 83.00 (15) |
C11—P1—C5A—C6A | −145.0 (2) | C16—C11—C12—C13 | −1.1 (3) |
O3—P1—C5A—C10A | 159.7 (2) | P1—C11—C12—C13 | 179.48 (19) |
C5B—P1—C5A—C10A | −169.2 (16) | C11—C12—C13—C14 | 0.3 (3) |
C17—P1—C5A—C10A | −76.8 (3) | C12—C13—C14—C15 | 0.6 (4) |
C11—P1—C5A—C10A | 36.4 (3) | C13—C14—C15—C16 | −0.7 (4) |
C10A—C5A—C6A—C7A | 0.0 | C12—C11—C16—C15 | 1.0 (3) |
P1—C5A—C6A—C7A | −178.6 (3) | P1—C11—C16—C15 | −179.6 (2) |
C5A—C6A—C7A—C8A | 0.0 | C14—C15—C16—C11 | −0.1 (4) |
C6A—C7A—C8A—C9A | 0.0 | O3—P1—C17—C22 | 146.5 (2) |
C7A—C8A—C9A—C10A | 0.0 | C5B—P1—C17—C22 | 27.4 (2) |
C8A—C9A—C10A—C5A | 0.0 | C11—P1—C17—C22 | −90.2 (2) |
C6A—C5A—C10A—C9A | 0.0 | C5A—P1—C17—C22 | 20.7 (3) |
P1—C5A—C10A—C9A | 178.5 (3) | O3—P1—C17—C18 | −32.4 (2) |
O3—P1—C5B—C6B | −26.77 (10) | C5B—P1—C17—C18 | −151.50 (19) |
C17—P1—C5B—C6B | 93.50 (11) | C11—P1—C17—C18 | 90.92 (18) |
C11—P1—C5B—C6B | −150.54 (9) | C5A—P1—C17—C18 | −158.1 (2) |
C5A—P1—C5B—C6B | −177.1 (14) | C22—C17—C18—C19 | −1.3 (3) |
O3—P1—C5B—C10B | 153.73 (14) | P1—C17—C18—C19 | 177.61 (18) |
C17—P1—C5B—C10B | −86.01 (16) | C17—C18—C19—C20 | 0.0 (4) |
C11—P1—C5B—C10B | 29.96 (18) | C18—C19—C20—C21 | 1.7 (4) |
C5A—P1—C5B—C10B | 3.4 (14) | C19—C20—C21—C22 | −2.1 (5) |
C10B—C5B—C6B—C7B | 0.0 | C20—C21—C22—C17 | 0.8 (5) |
P1—C5B—C6B—C7B | −179.52 (9) | C18—C17—C22—C21 | 0.9 (4) |
C5B—C6B—C7B—C8B | 0.0 | P1—C17—C22—C21 | −177.9 (2) |
C6B—C7B—C8B—C9B | 0.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 1.96 | 2.820 (2) | 173 |
C14—H14···O1i | 0.93 | 2.45 | 3.368 (3) | 170 |
C18—H18···O1 | 0.93 | 2.54 | 3.256 (3) | 135 |
C22—H22···O1ii | 0.93 | 2.55 | 3.283 (3) | 136 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H15OP·C4H5NO2 |
Mr | 377.36 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 8.5825 (4), 17.2754 (7), 26.6505 (11) |
V (Å3) | 3951.4 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.42 × 0.35 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26415, 3887, 2454 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.121, 1.02 |
No. of reflections | 3887 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.30 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 1.96 | 2.820 (2) | 173 |
C14—H14···O1i | 0.93 | 2.45 | 3.368 (3) | 170 |
C18—H18···O1 | 0.93 | 2.54 | 3.256 (3) | 135 |
C22—H22···O1ii | 0.93 | 2.55 | 3.283 (3) | 136 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z. |
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In the title 1:1 adduct, C18H15OP·C4H5NO2, (I), the component species interact by an almost linear N—H···O hydrogen bond (Table 1). The five-membered ring of the succinimide (suc) molecule in (I) is close to flat (r.m.s. deviation = 0.006 Å), similar to that in other suc-containing adducts (Elding-Pontén, 1993), whereas in succinimide itself (Mason, 1961), the ring is slightly puckered. One of the phenyl rings in the triphenylphosphine oxide (ppo) molecule in (I) is disordered over two positions, otherwise the geometric parameters for (I) may be regarded as normal (Allen et al., 1987). It is notable that although O1 accepts three of these putative bonds, and O2 none, the C1=O1 and C4=O2 bond lengths are identical.
Some weak C—H···O interactions (Table 1) from ppo to sac help establish the packing in (I). Aromatic π-π stacking interactions in (I) are negligible, as the minimum aromatic ring centroid···centroid separation is greater than 4.1 Å.