N-crotylphthalimide.

In the title compound {systematic name: 2-[(E)-but-2-en-1-yl]isoindoline-1,3-dione}, C(12)H(11)NO(2), the phthalimide ring system is essentially planar, with a maximum deviation of 0.008 (1) Å, while the plane of the N-crotyl substituent is orthogonal to the phthalimide ring system, making a dihedral angle of 87.5 (1)°.

Related literature

For related structures, see: Warzecha, Görner & Griesbeck (2006 ▶): Warzecha, Lex & Griesbeck (2006 ▶); Mustaphi et al. (2001 ▶). For details of inter­molecular inter­actions, see: Desiraju (1991 ▶); Steiner (2002 ▶); Etter et al. (1990 ▶). For the synthesis of N-crotylphtalimide, see: Roberts & Mazur (1951 ▶); Mowery et al. (2007 ▶).

Experimental

Crystal data

C12H11NO2

M = 201.22

Monoclinic,

a = 8.1880 (4) Å

b = 12.0830 (5) Å

c = 10.8080 (5) Å

β = 110.431 (4)°

V = 1002.03 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 123 K

0.36 × 0.32 × 0.2 mm

Data collection

Oxford Diffraction Gemini Atlas CCD diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.973, T max = 0.983

7022 measured reflections

1959 independent reflections

1669 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.080

S = 1.06

1959 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction (2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046039/is2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046039/is2623Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H11NO2	F(000) = 424
Mr = 201.22	Dx = 1.334 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1880 (4) Å	Cell parameters from 4695 reflections
b = 12.0830 (5) Å	θ = 3.8–26.0°
c = 10.8080 (5) Å	µ = 0.09 mm−1
β = 110.431 (4)°	T = 123 K
V = 1002.03 (8) Å3	Block, colorless
Z = 4	0.36 × 0.32 × 0.2 mm

Oxford Diffraction Gemini Atlas CCD diffractometer	1959 independent reflections
graphite	1669 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.016
ω scans	θmax = 26.1°, θmin = 3.9°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.973, Tmax = 0.983	k = −14→13
7022 measured reflections	l = −13→10

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) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.204P] where P = (Fo2 + 2Fc2)/3
1959 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.32549 (11)	0.11878 (7)	0.22557 (8)	0.0293 (2)
O2	−0.00316 (11)	0.09982 (7)	−0.21251 (8)	0.0299 (2)
N1	0.13954 (11)	0.13240 (7)	0.00921 (9)	0.0201 (2)
C3	0.21517 (14)	−0.02776 (9)	−0.07262 (11)	0.0200 (2)
C1	0.26809 (13)	0.08188 (9)	0.11487 (10)	0.0202 (2)
C8	0.31372 (14)	−0.02229 (9)	0.06096 (11)	0.0200 (2)
C7	0.43062 (14)	−0.10496 (10)	0.12205 (12)	0.0260 (3)
H7	0.4963	−0.1017	0.2116	0.031*
C11	0.19618 (14)	0.42523 (9)	0.04805 (11)	0.0237 (3)
H11	0.175	0.4284	0.1271	0.028*
C2	0.10193 (14)	0.07222 (9)	−0.10729 (10)	0.0204 (2)
C12	0.27941 (15)	0.52388 (9)	0.01158 (12)	0.0276 (3)
H12A	0.303	0.5085	−0.0677	0.041*
H12B	0.3866	0.5405	0.0819	0.041*
H12C	0.2022	0.5862	−0.0029	0.041*
C4	0.23032 (15)	−0.11498 (9)	−0.15043 (12)	0.0259 (3)
H4	0.1643	−0.1181	−0.24	0.031*
C9	0.05901 (14)	0.23939 (9)	0.01554 (11)	0.0229 (3)
H9A	0.0605	0.2512	0.1047	0.027*
H9B	−0.0617	0.2379	−0.0429	0.027*
C6	0.44640 (15)	−0.19339 (10)	0.04444 (13)	0.0307 (3)
H6	0.5239	−0.2503	0.0829	0.037*
C5	0.34873 (16)	−0.19817 (10)	−0.08913 (13)	0.0307 (3)
H5	0.3625	−0.258	−0.1387	0.037*
C10	0.15001 (14)	0.33373 (9)	−0.02266 (11)	0.0217 (3)
H10	0.1753	0.3277	−0.0999	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0324 (5)	0.0331 (5)	0.0201 (4)	−0.0027 (4)	0.0062 (4)	−0.0045 (3)
O2	0.0310 (5)	0.0331 (5)	0.0208 (4)	0.0034 (4)	0.0031 (4)	0.0009 (3)
N1	0.0217 (5)	0.0184 (5)	0.0202 (5)	0.0006 (4)	0.0073 (4)	−0.0009 (4)
C3	0.0203 (5)	0.0184 (5)	0.0235 (6)	−0.0041 (4)	0.0106 (4)	0.0005 (4)
C1	0.0197 (5)	0.0218 (6)	0.0201 (6)	−0.0037 (4)	0.0081 (5)	0.0013 (4)
C8	0.0188 (5)	0.0194 (6)	0.0239 (6)	−0.0039 (4)	0.0099 (4)	0.0015 (4)
C7	0.0210 (6)	0.0256 (6)	0.0312 (6)	−0.0014 (5)	0.0088 (5)	0.0071 (5)
C11	0.0219 (6)	0.0254 (6)	0.0243 (6)	0.0029 (5)	0.0084 (5)	0.0019 (5)
C2	0.0199 (5)	0.0215 (6)	0.0204 (6)	−0.0036 (4)	0.0079 (5)	0.0001 (4)
C12	0.0249 (6)	0.0228 (6)	0.0335 (7)	0.0003 (5)	0.0083 (5)	0.0007 (5)
C4	0.0304 (6)	0.0220 (6)	0.0293 (6)	−0.0064 (5)	0.0154 (5)	−0.0039 (5)
C9	0.0228 (6)	0.0199 (6)	0.0278 (6)	0.0023 (4)	0.0112 (5)	−0.0013 (4)
C6	0.0254 (6)	0.0206 (6)	0.0503 (8)	0.0025 (5)	0.0185 (6)	0.0080 (5)
C5	0.0360 (7)	0.0181 (6)	0.0470 (8)	−0.0027 (5)	0.0259 (6)	−0.0035 (5)
C10	0.0202 (5)	0.0219 (6)	0.0242 (6)	0.0033 (4)	0.0093 (5)	0.0021 (4)

O1—C1	1.2076 (13)	C11—H11	0.93
O2—C2	1.2091 (13)	C12—H12A	0.96
N1—C2	1.3923 (14)	C12—H12B	0.96
N1—C1	1.3948 (14)	C12—H12C	0.96
N1—C9	1.4637 (14)	C4—C5	1.3931 (17)
C3—C4	1.3807 (15)	C4—H4	0.93
C3—C8	1.3880 (16)	C9—C10	1.4966 (15)
C3—C2	1.4888 (15)	C9—H9A	0.97
C1—C8	1.4885 (15)	C9—H9B	0.97
C8—C7	1.3815 (16)	C6—C5	1.3860 (18)
C7—C6	1.3920 (17)	C6—H6	0.93
C7—H7	0.93	C5—H5	0.93
C11—C10	1.3220 (16)	C10—H10	0.93
C11—C12	1.4926 (16)
C2—N1—C1	112.17 (9)	H12A—C12—H12B	109.5
C2—N1—C9	122.86 (9)	C11—C12—H12C	109.5
C1—N1—C9	124.88 (9)	H12A—C12—H12C	109.5
C4—C3—C8	121.78 (10)	H12B—C12—H12C	109.5
C4—C3—C2	130.28 (10)	C3—C4—C5	117.17 (11)
C8—C3—C2	107.94 (9)	C3—C4—H4	121.4
O1—C1—N1	124.83 (10)	C5—C4—H4	121.4
O1—C1—C8	129.49 (10)	N1—C9—C10	112.59 (9)
N1—C1—C8	105.68 (9)	N1—C9—H9A	109.1
C7—C8—C3	121.13 (10)	C10—C9—H9A	109.1
C7—C8—C1	130.62 (10)	N1—C9—H9B	109.1
C3—C8—C1	108.25 (9)	C10—C9—H9B	109.1
C8—C7—C6	117.49 (11)	H9A—C9—H9B	107.8
C8—C7—H7	121.3	C5—C6—C7	121.23 (11)
C6—C7—H7	121.3	C5—C6—H6	119.4
C10—C11—C12	125.45 (11)	C7—C6—H6	119.4
C10—C11—H11	117.3	C6—C5—C4	121.20 (11)
C12—C11—H11	117.3	C6—C5—H5	119.4
O2—C2—N1	124.52 (10)	C4—C5—H5	119.4
O2—C2—C3	129.55 (10)	C11—C10—C9	123.16 (10)
N1—C2—C3	105.93 (9)	C11—C10—H10	118.4
C11—C12—H12A	109.5	C9—C10—H10	118.4
C11—C12—H12B	109.5
C2—N1—C1—O1	178.65 (10)	C1—N1—C2—C3	1.06 (12)
C9—N1—C1—O1	2.11 (17)	C9—N1—C2—C3	177.68 (9)
C2—N1—C1—C8	−1.51 (12)	C4—C3—C2—O2	−0.1 (2)
C9—N1—C1—C8	−178.05 (9)	C8—C3—C2—O2	179.95 (11)
C4—C3—C8—C7	−0.57 (16)	C4—C3—C2—N1	179.84 (11)
C2—C3—C8—C7	179.40 (9)	C8—C3—C2—N1	−0.13 (11)
C4—C3—C8—C1	179.26 (10)	C8—C3—C4—C5	0.25 (16)
C2—C3—C8—C1	−0.77 (11)	C2—C3—C4—C5	−179.71 (10)
O1—C1—C8—C7	1.02 (19)	C2—N1—C9—C10	−83.65 (12)
N1—C1—C8—C7	−178.81 (11)	C1—N1—C9—C10	92.53 (12)
O1—C1—C8—C3	−178.78 (11)	C8—C7—C6—C5	0.12 (17)
N1—C1—C8—C3	1.39 (11)	C7—C6—C5—C4	−0.43 (17)
C3—C8—C7—C6	0.37 (16)	C3—C4—C5—C6	0.24 (16)
C1—C8—C7—C6	−179.42 (10)	C12—C11—C10—C9	−176.94 (10)
C1—N1—C2—O2	−179.01 (10)	N1—C9—C10—C11	−131.59 (11)
C9—N1—C2—O2	−2.39 (16)