1,7,8,9,10,10-Hexachloro-4-(thio­phen-2-ylmeth­yl)-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/S1600536811032788

. 2011 Aug 27;67(Pt 9):o2391. doi: 10.1107/S1600536811032788

1,7,8,9,10,10-Hexachloro-4-(thiophen-2-ylmethyl)-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: PMC3200576 PMID: 22058988

Abstract

In the title compound, C₁₄H₇Cl₆NO₂S, the six-membered ring of the azatricyclo system has a boat conformation whereas the five-membered rings have an envelope conformation. The thiophene ring and the ring of the succinimide moiety enclose a dihedral angle of 67.2 (1)°. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of cyclic imides, see: Duarte et al. (2006 ▶); Nakamura et al. (2006 ▶); Stefańska et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₇Cl₆NO₂S
M _r = 465.97
Tetragonal,
a = 23.8136 (10) Å
c = 12.6240 (9) Å
V = 7158.9 (7) Å³
Z = 16
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm Is this OK?

Data collection

Xcalibur, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.978, T _max = 0.984
8488 measured reflections
4156 independent reflections
2283 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.075
S = 0.82
4156 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 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) I, global. DOI: 10.1107/S1600536811032788/bt5586sup1.cif

e-67-o2391-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032788/bt5586Isup2.hkl

e-67-o2391-Isup2.hkl^{(199.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032788/bt5586Isup3.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⋯O2ⁱ	0.98	2.54	3.064 (3)	113
C6—H6⋯O2ⁱ	0.98	2.51	3.042 (3)	114

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Symmetry code: (i) Inline graphic .

Acknowledgments

CRR is grateful to the DST–FIST single-crystal X-ray facility of the Department of Chemistry, Pondicherry University, Pondicherry.

supplementary crystallographic information

Comment

Azatricyclo dec-8-ene 3,5 dione derivatives have anti bacterial and anti fungal activities with other important biological activities (Stefańska et al., 2010).

In these structure, the six-membered ring of the norbornene moiety adopts a boat conformation whereas the two five-membered rings adopt envelope conformation.The fusion at atoms C6 and C2 is in cis conformation. The planarity around N4 and C3—N4 [1.38 (4) Å] and N4—C5 [1.38 (4) Å] reveals the partial double bond charater to facilitate the electron delocalization from one keto oxygen to other through N4. The crystal structure is stabilized by weak inter-molecular C-H···O interactions.

Experimental

1-(thiophen-2-yl)methanamine (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-(thiophen-2-yl-methyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione, in 92% yield as colorless solid.