In the title compound (systematic name: 2-allylisoindoline-1,3-dione), C
11H
9NO
2, the synperiplanar allyl substituent is orthogonal to the phthalimide ring plane. In the crystal structure, pairwise C
aryl—H
O=C bonds furnish ribbons of
R(10) motifs along the crystallographic
b axis. Parallel layers of ribbons are crosslinked by additional C
vinyl—H
O bonds.
Supporting information
CCDC reference: 630454
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.002 Å
- R factor = 0.039
- wR factor = 0.095
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
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Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and enCIFer (Allen et al.,
2004).
2-allylisoindoline-1,3-dione
top
Crystal data top
C11H9NO2 | Dx = 1.372 Mg m−3 |
Mr = 187.19 | Melting point: 345 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3914 (3) Å | Cell parameters from 4595 reflections |
b = 14.1284 (5) Å | θ = 2.7–27.0° |
c = 7.1083 (2) Å | µ = 0.10 mm−1 |
β = 106.094 (1)° | T = 100 K |
V = 906.20 (5) Å3 | Platelet, colourless |
Z = 4 | 0.55 × 0.35 × 0.18 mm |
F(000) = 392 | |
Data collection top
Nonius KappaCCD diffractometer | 1330 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 27.0°, θmin = 2.7° |
φ and ω scans | h = −11→11 |
4595 measured reflections | k = −16→18 |
1949 independent reflections | l = −6→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | All H-atom parameters refined |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0423P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.005 |
1949 reflections | Δρmax = 0.27 e Å−3 |
165 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (6) |
Special details top
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 | |
C1 | 0.62234 (14) | 0.03671 (10) | 0.86964 (17) | 0.0193 (3) | |
C2 | 0.62634 (14) | 0.20062 (10) | 0.86666 (17) | 0.0199 (3) | |
C3 | 0.48258 (13) | 0.16849 (9) | 0.73214 (16) | 0.0189 (3) | |
C4 | 0.36455 (14) | 0.22022 (10) | 0.62032 (17) | 0.0213 (3) | |
H4 | 0.3651 (13) | 0.2876 (10) | 0.6212 (15) | 0.020 (4)* | |
C5 | 0.24403 (14) | 0.16915 (11) | 0.50792 (18) | 0.0239 (3) | |
H5 | 0.1596 (14) | 0.2030 (10) | 0.4306 (17) | 0.032 (4)* | |
C6 | 0.24247 (14) | 0.07116 (11) | 0.50873 (17) | 0.0231 (4) | |
H6 | 0.1543 (13) | 0.0385 (10) | 0.4284 (17) | 0.034 (4)* | |
C7 | 0.36156 (14) | 0.01920 (11) | 0.62223 (17) | 0.0208 (3) | |
H7 | 0.3626 (12) | −0.0481 (10) | 0.6243 (15) | 0.019 (3)* | |
C8 | 0.48087 (13) | 0.07013 (9) | 0.73372 (16) | 0.0178 (3) | |
C9 | 0.84978 (14) | 0.11650 (10) | 1.08086 (18) | 0.0225 (3) | |
H9A | 0.8580 (13) | 0.1711 (9) | 1.1740 (17) | 0.026 (4)* | |
H9B | 0.8583 (14) | 0.0555 (10) | 1.1593 (18) | 0.032 (4)* | |
C10 | 0.97259 (14) | 0.12097 (9) | 0.98334 (18) | 0.0232 (3) | |
H10 | 1.0696 (15) | 0.1124 (8) | 1.0726 (18) | 0.028 (4)* | |
C11 | 0.95712 (16) | 0.13300 (10) | 0.7952 (2) | 0.0273 (4) | |
H11A | 0.8618 (15) | 0.1404 (8) | 0.7011 (18) | 0.023 (3)* | |
H11B | 1.0483 (16) | 0.1349 (9) | 0.7486 (19) | 0.040 (4)* | |
N1 | 0.70212 (11) | 0.11826 (7) | 0.94358 (14) | 0.0197 (3) | |
O1 | 0.66446 (9) | −0.04321 (7) | 0.91383 (11) | 0.0248 (3) | |
O2 | 0.67287 (10) | 0.28016 (7) | 0.90604 (12) | 0.0260 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0250 (7) | 0.0146 (9) | 0.0212 (7) | 0.0015 (6) | 0.0115 (6) | 0.0011 (6) |
C2 | 0.0239 (7) | 0.0145 (8) | 0.0239 (7) | −0.0001 (6) | 0.0112 (6) | −0.0004 (6) |
C3 | 0.0213 (7) | 0.0175 (8) | 0.0208 (7) | 0.0019 (6) | 0.0105 (5) | −0.0002 (5) |
C4 | 0.0252 (8) | 0.0157 (9) | 0.0247 (7) | 0.0021 (6) | 0.0099 (6) | 0.0003 (6) |
C5 | 0.0224 (8) | 0.0252 (10) | 0.0243 (7) | 0.0058 (7) | 0.0071 (6) | 0.0018 (6) |
C6 | 0.0223 (8) | 0.0241 (10) | 0.0233 (7) | −0.0029 (6) | 0.0070 (6) | −0.0039 (6) |
C7 | 0.0258 (8) | 0.0166 (9) | 0.0228 (7) | −0.0014 (6) | 0.0115 (6) | −0.0016 (6) |
C8 | 0.0208 (7) | 0.0159 (8) | 0.0195 (6) | 0.0019 (6) | 0.0104 (6) | −0.0001 (5) |
C9 | 0.0224 (7) | 0.0201 (9) | 0.0225 (7) | 0.0001 (6) | 0.0024 (5) | −0.0001 (6) |
C10 | 0.0192 (7) | 0.0181 (8) | 0.0294 (7) | 0.0002 (6) | 0.0021 (6) | 0.0000 (6) |
C11 | 0.0252 (8) | 0.0235 (10) | 0.0341 (8) | −0.0007 (6) | 0.0099 (7) | −0.0002 (6) |
N1 | 0.0196 (6) | 0.0143 (7) | 0.0247 (6) | −0.0008 (5) | 0.0056 (5) | −0.0006 (5) |
O1 | 0.0300 (6) | 0.0161 (6) | 0.0283 (5) | 0.0030 (4) | 0.0083 (4) | 0.0029 (4) |
O2 | 0.0274 (6) | 0.0148 (6) | 0.0345 (5) | −0.0027 (4) | 0.0065 (4) | −0.0024 (4) |
Geometric parameters (Å, º) top
C1—O1 | 1.2088 (15) | C6—C7 | 1.3930 (18) |
C1—N1 | 1.3952 (16) | C6—H6 | 0.981 (13) |
C1—C8 | 1.4866 (17) | C7—C8 | 1.3817 (17) |
C2—O2 | 1.2102 (16) | C7—H7 | 0.950 (14) |
C2—N1 | 1.3941 (17) | C9—N1 | 1.4580 (16) |
C2—C3 | 1.4924 (17) | C9—C10 | 1.5027 (17) |
C3—C4 | 1.3807 (17) | C9—H9A | 1.006 (12) |
C3—C8 | 1.3898 (18) | C9—H9B | 1.017 (14) |
C4—C5 | 1.3924 (18) | C10—C11 | 1.3157 (18) |
C4—H4 | 0.952 (14) | C10—H10 | 0.963 (14) |
C5—C6 | 1.385 (2) | C11—H11A | 0.963 (13) |
C5—H5 | 0.958 (13) | C11—H11B | 1.001 (14) |
| | | |
O1—C1—N1 | 124.79 (13) | C6—C7—H7 | 122.6 (7) |
O1—C1—C8 | 129.40 (13) | C7—C8—C3 | 121.70 (12) |
N1—C1—C8 | 105.81 (11) | C7—C8—C1 | 130.08 (13) |
O2—C2—N1 | 124.89 (13) | C3—C8—C1 | 108.21 (11) |
O2—C2—C3 | 129.43 (14) | N1—C9—C10 | 113.56 (10) |
N1—C2—C3 | 105.68 (11) | N1—C9—H9A | 108.2 (7) |
C4—C3—C8 | 121.65 (12) | C10—C9—H9A | 110.0 (7) |
C4—C3—C2 | 130.33 (13) | N1—C9—H9B | 107.3 (7) |
C8—C3—C2 | 108.02 (11) | C10—C9—H9B | 109.5 (7) |
C3—C4—C5 | 116.82 (13) | H9A—C9—H9B | 108.0 (10) |
C3—C4—H4 | 121.6 (8) | C11—C10—C9 | 126.28 (13) |
C5—C4—H4 | 121.6 (8) | C11—C10—H10 | 120.3 (7) |
C6—C5—C4 | 121.58 (13) | C9—C10—H10 | 113.4 (7) |
C6—C5—H5 | 119.5 (9) | C10—C11—H11A | 122.6 (7) |
C4—C5—H5 | 118.9 (9) | C10—C11—H11B | 118.4 (8) |
C5—C6—C7 | 121.44 (13) | H11A—C11—H11B | 118.9 (10) |
C5—C6—H6 | 118.5 (8) | C2—N1—C1 | 112.27 (11) |
C7—C6—H6 | 120.1 (8) | C2—N1—C9 | 124.34 (11) |
C8—C7—C6 | 116.81 (14) | C1—N1—C9 | 123.36 (11) |
C8—C7—H7 | 120.6 (7) | | |
| | | |
N1—C9—C10—C11 | 5.3 (2) | C10—C9—N1—C2 | −84.85 (15) |
C10—C9—N1—C1 | 93.13 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.952 (14) | 2.411 (14) | 3.3568 (17) | 172.0 (10) |
C7—H7···O2ii | 0.951 (14) | 2.451 (14) | 3.3933 (18) | 171.2 (10) |
C11—H11A···O2iii | 0.963 (14) | 2.597 (13) | 3.4914 (17) | 154.6 (10) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z−1/2. |