N-(4-tert-Butyl­benz­yl)phthalimide

Jiang-Sheng Li; Jim Simpson; Xun Li

doi:10.1107/S1600536809025343

. 2009 Jul 4;65(Pt 8):o1779. doi: 10.1107/S1600536809025343

N-(4-tert-Butylbenzyl)phthalimide

Jiang-Sheng Li ^a,^*, Jim Simpson ^b, Xun Li ^a

PMCID: PMC2977282 PMID: 21583486

Abstract

The molecule of the title compound [systematic name: 2-(4-tert-butylbenzyl)isoindoline-1,3-dione], C₁₉H₁₉NO₂, is V-shaped with a dihedral angle of 74.15 (7)° between the mean planes of the phthalimide unit and the benzene ring. The methyl groups of the tert-butyl substituent are disordered over two sets of positions, with an occupancy ratio of 0.700 (4):0.300 (4). In the crystal, intermolecular C—H⋯O hydrogen bonds link adjacent molecules into centrosymmetric dimers. An additional weak C—H⋯O contact, together with weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.961 (2) Å] generate a three-dimensional network.

Related literature

For the synthesis, see: Xin et al. (2006 ▶). For related structures, see: Chen et al. (2006 ▶); Lü et al. (2006 ▶); Warzecha et al. (2006a ▶,b ▶,c ▶); Xin et al. (2006 ▶).For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₉NO₂
M _r = 293.35
Trigonal,
a = 37.576 (7) Å
c = 6.2970 (16) Å
V = 7700 (3) Å³
Z = 18
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.983, T _max = 0.987
13205 measured reflections
3022 independent reflections
1574 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.139
S = 1.01
3022 reflections
232 parameters
117 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks gloabl, I. DOI: 10.1107/S1600536809025343/hb5020sup1.cif

e-65-o1779-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025343/hb5020Isup2.hkl

e-65-o1779-Isup2.hkl^{(148.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.93	2.41	3.297 (3)	160
C9—H9B⋯O1ⁱⁱ	0.97	2.71	3.135 (3)	107
C5—H5A⋯Cg3ⁱⁱⁱ	0.93	2.94	3.771 (4)	149

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg3 is the centroid of the C10–C15 benzene ring.

Acknowledgments

This project was supported by the Changsha University of Science and Technology Talent Fund (Project No. 1004214)

supplementary crystallographic information

Comment

The molecular structure of (I) (Fig. 1) shows that the phthalimide ring system is almost planar, with the dihedral angle between the C2···C7 and N1/C1/C2/C7/C8 rings 1.26 (15) °. The molecule adopts a V-shape with a dihedral angle between the mean planes of the phthalimide group and the benzene ring of 74.12 (7) Å. Bond distances within the molecule are normal (Allen et al., 1987) and similar to those observed in comparable structures (Chen et al., 2006; Lü et al., 2006; Warzecha et al., 2006a,b,c; Xin et al., 2006).

In the crystal structure, complementary intermolecular C6—H6a···O2 hydrogen bonds link molecules into dimers (Table 1, Fig. 2). Additional weak C8—H9B···O1 and C—H···π contacts together with π-π interactions between the six-membered phthalimide rings (centroid-centroid separation 3.961 (2) Å; 1/3 - x,2/3 - y,2/3 - z) generate an extensive three-dimensional network structure, Fig. 3.

Experimental

The title compound was obtained by a literature method (Xin, et al., 2006). Colourless blocks of (I) were grown from an ethanol solution.