N-Allyl­phthalimide: parallel ribbons of R(10) motifs crosslinked by C_vin­yl—H...O bonds

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 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.

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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Computing details

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

Crystal data

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) Å^3	Platelet, colourless
Z = 4	0.55 × 0.35 × 0.18 mm
F(000) = 392

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	All H-atom parameters refined
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0423P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (6)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.952 (14)	2.411 (14)	3.3568 (17)	172.0 (10)
C7—H7···O2^ii	0.951 (14)	2.451 (14)	3.3933 (18)	171.2 (10)
C11—H11A···O2^iii	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.