1,7,8,9,10,10-Hexachloro-4-(2-phenyl­eth­yl)-4-aza­tricyclo­[5.2.1.02,6]dec-8-ene-3,5-dione

R Manohar; M Harikrishna; C R Ramanathan; M SureshKumar; K Gunasekaran

doi:10.1107/S1600536811022495

. 2011 Jun 18;67(Pt 7):o1708. doi: 10.1107/S1600536811022495

1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

R Manohar ^a, M Harikrishna ^b, C R Ramanathan ^b, M SureshKumar ^c, K Gunasekaran ^a,^*

PMCID: PMC3151925 PMID: 21837102

Abstract

In the title compound, C₁₇H₁₁Cl₆NO₂, the six-membered ring of the norbornene moiety adopts a boat conformation whereas the two five-membered rings adopt envelope conformations. The phenyl ring and the ring of the succinimide moiety are almost coplanar [dihedral angle = 7.44 (14)°]. The crystal packing is stabilized by a weak intermolecular C—H⋯O hydrogen bond.

Related literature

The interest in cyclic imides is due to their biological activity and wide application in the pharmaceutical industry, see: Duarte et al. (2006 ▶); Nakamura et al. (2006 ▶); Stefańska et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₁Cl₆NO₂
M _r = 473.97
Monoclinic,
a = 13.3009 (5) Å
b = 13.6141 (5) Å
c = 11.4912 (4) Å
β = 111.276 (4)°
V = 1939.00 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.978, T _max = 0.984
9237 measured reflections
4457 independent reflections
2814 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.121
S = 0.72
4457 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022495/bt5543sup1.cif

e-67-o1708-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022495/bt5543Isup2.hkl

e-67-o1708-Isup2.hkl^{(214KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022495/bt5543Isup3.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—H1⋯O2ⁱ	0.91 (3)	2.50 (3)	3.235 (3)	138 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

CRR thanks DST-FIST for the single-crystal X-ray facility at the Department of Chemistry, Pondicherry University, Pondicherry.

supplementary crystallographic information

Comment

The ORTEP diagram for the molecule of the title compound is given in Fig. 1. In the crystal structure, the phenyl and the azatricyclo substitutions are in anti conformation about the C11—C12 bond which is confirmed by the torsion angle N4—C11—C12—C13 [169.3 (3)°]. In the crystal, molecules are linked by weak intermolecular C—H···O hydrogen bonds.

Experimental

Phenethylamine (1 equiv) and 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic anhydride (1 equiv) were stirred at room temperature in dry ethyl acetate for 30 min. Ethyl acetate was removed under reduced pressure; the resulting residue was dissolved in toluene. To this reaction mixture was added acetyl chloride (5 equiv) and refluxed for 1 h. The reaction mixture was brought to room temperature and washed with aqueous Na2CO3 and dried over anhydrous Na₂SO₄. Filtered and concentrated under reduced pressure followed by silica gel column purification afforded the imide,1,7,8,9,10,10-Hexachloro-4-(2-phenylethyl)-4-azatricyclo [5.2.1.02,6]dec-8-ene-3,5-dione,in 55% yield as colourless solid (m.p.: 161–163°C).