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In the title compound (systematic name: 2-allyl­isoindoline-1,3-dione), C11H9NO2, the synperiplanar allyl substituent is orthogonal to the phthalimide ring plane. In the crystal structure, pairwise Car­yl—H...O=C bonds furnish ribbons of R(10) motifs along the crystallographic b axis. Parallel layers of ribbons are crosslinked by additional Cvin­yl—H...O bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604596X/sg2082sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604596X/sg2082Isup2.hkl
Contains datablock I

CCDC reference: 630454

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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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No errors found in this datablock

Computing details top

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
C11H9NO2Dx = 1.372 Mg m3
Mr = 187.19Melting point: 345 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.3914 (3) ÅCell parameters from 4595 reflections
b = 14.1284 (5) Åθ = 2.7–27.0°
c = 7.1083 (2) ŵ = 0.10 mm1
β = 106.094 (1)°T = 100 K
V = 906.20 (5) Å3Platelet, colourless
Z = 40.55 × 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 tubeRint = 0.052
Graphite monochromatorθmax = 27.0°, θmin = 2.7°
φ and ω scansh = 1111
4595 measured reflectionsk = 1618
1949 independent reflectionsl = 69
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039All 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 reflectionsΔρmax = 0.27 e Å3
165 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.62234 (14)0.03671 (10)0.86964 (17)0.0193 (3)
C20.62634 (14)0.20062 (10)0.86666 (17)0.0199 (3)
C30.48258 (13)0.16849 (9)0.73214 (16)0.0189 (3)
C40.36455 (14)0.22022 (10)0.62032 (17)0.0213 (3)
H40.3651 (13)0.2876 (10)0.6212 (15)0.020 (4)*
C50.24403 (14)0.16915 (11)0.50792 (18)0.0239 (3)
H50.1596 (14)0.2030 (10)0.4306 (17)0.032 (4)*
C60.24247 (14)0.07116 (11)0.50873 (17)0.0231 (4)
H60.1543 (13)0.0385 (10)0.4284 (17)0.034 (4)*
C70.36156 (14)0.01920 (11)0.62223 (17)0.0208 (3)
H70.3626 (12)0.0481 (10)0.6243 (15)0.019 (3)*
C80.48087 (13)0.07013 (9)0.73372 (16)0.0178 (3)
C90.84978 (14)0.11650 (10)1.08086 (18)0.0225 (3)
H9A0.8580 (13)0.1711 (9)1.1740 (17)0.026 (4)*
H9B0.8583 (14)0.0555 (10)1.1593 (18)0.032 (4)*
C100.97259 (14)0.12097 (9)0.98334 (18)0.0232 (3)
H101.0696 (15)0.1124 (8)1.0726 (18)0.028 (4)*
C110.95712 (16)0.13300 (10)0.7952 (2)0.0273 (4)
H11A0.8618 (15)0.1404 (8)0.7011 (18)0.023 (3)*
H11B1.0483 (16)0.1349 (9)0.7486 (19)0.040 (4)*
N10.70212 (11)0.11826 (7)0.94358 (14)0.0197 (3)
O10.66446 (9)0.04321 (7)0.91383 (11)0.0248 (3)
O20.67287 (10)0.28016 (7)0.90604 (12)0.0260 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0250 (7)0.0146 (9)0.0212 (7)0.0015 (6)0.0115 (6)0.0011 (6)
C20.0239 (7)0.0145 (8)0.0239 (7)0.0001 (6)0.0112 (6)0.0004 (6)
C30.0213 (7)0.0175 (8)0.0208 (7)0.0019 (6)0.0105 (5)0.0002 (5)
C40.0252 (8)0.0157 (9)0.0247 (7)0.0021 (6)0.0099 (6)0.0003 (6)
C50.0224 (8)0.0252 (10)0.0243 (7)0.0058 (7)0.0071 (6)0.0018 (6)
C60.0223 (8)0.0241 (10)0.0233 (7)0.0029 (6)0.0070 (6)0.0039 (6)
C70.0258 (8)0.0166 (9)0.0228 (7)0.0014 (6)0.0115 (6)0.0016 (6)
C80.0208 (7)0.0159 (8)0.0195 (6)0.0019 (6)0.0104 (6)0.0001 (5)
C90.0224 (7)0.0201 (9)0.0225 (7)0.0001 (6)0.0024 (5)0.0001 (6)
C100.0192 (7)0.0181 (8)0.0294 (7)0.0002 (6)0.0021 (6)0.0000 (6)
C110.0252 (8)0.0235 (10)0.0341 (8)0.0007 (6)0.0099 (7)0.0002 (6)
N10.0196 (6)0.0143 (7)0.0247 (6)0.0008 (5)0.0056 (5)0.0006 (5)
O10.0300 (6)0.0161 (6)0.0283 (5)0.0030 (4)0.0083 (4)0.0029 (4)
O20.0274 (6)0.0148 (6)0.0345 (5)0.0027 (4)0.0065 (4)0.0024 (4)
Geometric parameters (Å, º) top
C1—O11.2088 (15)C6—C71.3930 (18)
C1—N11.3952 (16)C6—H60.981 (13)
C1—C81.4866 (17)C7—C81.3817 (17)
C2—O21.2102 (16)C7—H70.950 (14)
C2—N11.3941 (17)C9—N11.4580 (16)
C2—C31.4924 (17)C9—C101.5027 (17)
C3—C41.3807 (17)C9—H9A1.006 (12)
C3—C81.3898 (18)C9—H9B1.017 (14)
C4—C51.3924 (18)C10—C111.3157 (18)
C4—H40.952 (14)C10—H100.963 (14)
C5—C61.385 (2)C11—H11A0.963 (13)
C5—H50.958 (13)C11—H11B1.001 (14)
O1—C1—N1124.79 (13)C6—C7—H7122.6 (7)
O1—C1—C8129.40 (13)C7—C8—C3121.70 (12)
N1—C1—C8105.81 (11)C7—C8—C1130.08 (13)
O2—C2—N1124.89 (13)C3—C8—C1108.21 (11)
O2—C2—C3129.43 (14)N1—C9—C10113.56 (10)
N1—C2—C3105.68 (11)N1—C9—H9A108.2 (7)
C4—C3—C8121.65 (12)C10—C9—H9A110.0 (7)
C4—C3—C2130.33 (13)N1—C9—H9B107.3 (7)
C8—C3—C2108.02 (11)C10—C9—H9B109.5 (7)
C3—C4—C5116.82 (13)H9A—C9—H9B108.0 (10)
C3—C4—H4121.6 (8)C11—C10—C9126.28 (13)
C5—C4—H4121.6 (8)C11—C10—H10120.3 (7)
C6—C5—C4121.58 (13)C9—C10—H10113.4 (7)
C6—C5—H5119.5 (9)C10—C11—H11A122.6 (7)
C4—C5—H5118.9 (9)C10—C11—H11B118.4 (8)
C5—C6—C7121.44 (13)H11A—C11—H11B118.9 (10)
C5—C6—H6118.5 (8)C2—N1—C1112.27 (11)
C7—C6—H6120.1 (8)C2—N1—C9124.34 (11)
C8—C7—C6116.81 (14)C1—N1—C9123.36 (11)
C8—C7—H7120.6 (7)
N1—C9—C10—C115.3 (2)C10—C9—N1—C284.85 (15)
C10—C9—N1—C193.13 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.952 (14)2.411 (14)3.3568 (17)172.0 (10)
C7—H7···O2ii0.951 (14)2.451 (14)3.3933 (18)171.2 (10)
C11—H11A···O2iii0.963 (14)2.597 (13)3.4914 (17)154.6 (10)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z1/2.
 

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