2-(2-Bromo­eth­yl)isoindoline-1,3-dione

Xiao-Qiang Sun; Dong An; Ying Shao

doi:10.1107/S1600536811039808

. 2011 Oct 5;67(Pt 11):o2832. doi: 10.1107/S1600536811039808

2-(2-Bromoethyl)isoindoline-1,3-dione

Xiao-Qiang Sun ^a, Dong An ^a, Ying Shao ^a,^*

PMCID: PMC3247571 PMID: 22219876

Abstract

The asymmetric unit of the title compound, C₁₀H₈BrNO₂, contains three crystallographically independent molecules. Two of the N—C—C—Br side chains adopt anti conformations [torsion angles = −179.8 (5) and −179.4 (4)°] and the other is gauche [−66.5 (6)°]. The crystal structure features short Br⋯O [3.162 (5) Å] contacts, C—H⋯O hydrogen bonds and numerous π–π stacking interactions [centroid–centroid separations = 3.517 (4)–3.950 (4) Å].

Related literature

For general background to and applications of the title compound, see: Sheng et al. (2007 ▶). For the preparation, see: Clouet & Juhl (1994 ▶).

Experimental

Crystal data

C₁₀H₈BrNO₂
M _r = 254.08
Triclinic,
a = 8.575 (2) Å
b = 11.067 (3) Å
c = 16.333 (5) Å
α = 99.001 (6)°
β = 96.164 (5)°
γ = 102.259 (6)°
V = 1480.2 (7) Å³
Z = 6
Mo Kα radiation
μ = 4.14 mm⁻¹
T = 297 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.370, T _max = 0.437
7716 measured reflections
5043 independent reflections
3241 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.177
S = 1.00
5043 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039808/hb6417sup1.cif

e-67-o2832-sup1.cif^{(34.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039808/hb6417Isup2.hkl

e-67-o2832-Isup2.hkl^{(247KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039808/hb6417Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811039808/hb6417Isup4.cml

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
C2—H2⋯O6ⁱ	0.93	2.59	3.301 (9)	133
C10—H10A⋯O3ⁱⁱ	0.97	2.48	3.409 (8)	161
C10—H10B⋯O5ⁱⁱⁱ	0.97	2.60	3.533 (9)	163
C13—H13⋯O4^iv	0.93	2.52	3.448 (8)	175
C14—H14⋯O1	0.93	2.59	3.495 (10)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We gratefully acknowledge Changzhou University and the Key Laboratory of Fine Chemical Engineering of Jiangsu Province for financial support (ZMF10020010 and SCZ10102271B).

supplementary crystallographic information

Comment

The title compound, C₁₀H₈BrNO₂, which is an important aminoethylation reagent in the classic Gabriel Synthesis (Sheng et al., 2007), was prepared by nucleophilic substitution of 1,2-dibromoethane with potassium phthalimide in DMF at room temperature (Clouet et al., 1994). The title compound crystallizes in space group P1 with three crystallographically independent molecules in the asymmetric unit, designated A, B and C (Fig. 1). In the crystal, the phthalimide rings are almost coplanar [r.m.s. deviations = 0.0681 (A), 0.0125 (B), 0.0113 (C) Å, respectively]. The molecular geometries of all molecules are essentiall similar, except for the BrCH₂CH₂ groups adopting slightly different zigzag conformations.

An interesting feature of the crystal structure is the short non-hydrogen Br···O interactions (table 1), together with intra- and inter-molecular C—H···O hydrogen bonding interactions (table 2), which links the molecules into an extended three-dimensional network, as shown in Fig. 2. The crystal structure is further stabilized by intermolecular π–π stacking interactions invoving the benzene and maleinimide rings [centroid-centroid distances = 3.517 (4) - 3.950 (4) Å].

Experimental

The title compound was prepared according to literature procedures (Clouet et al., 1994). Yield: 86%. Colourless blocks were obtained by slow evaporation of EtOH.