proofs BT5586
Acta Crystallographica Section E
Structure Reports Online ISSN 1600-5368
1,7,8,9,10,10-Hexachloro-4-(thiophen-2-ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8ene-3,5-dione Manohar et al. Synopsis
Queries and comments Please supply or correct as appropriate all bold underlined text. In describing corrections please refer to line numbers where appropriate: these are shown in grey.
Author index Authors’ names will normally be arranged alphabetically under their family name and this is commonly their last name. Prefixes (van, de etc.) will only be taken into account in the alphabetization if they begin with a capital letter. Authors wishing their names to be alphabetized differently should indicate this below. Author names may appear more than once in this list; it is not necessary to mark this correction on your proofs. Manohar, R. Harikrishna, M. Ramanathan, C.R. SureshKumar, M. Gunasekaran, K.
Important notice This article is in the new shorter format that was introduced in March 2007 for all articles submitted to Acta Crystallographica Section E: Structure Reports Online. For more information, please visit http://journals.iucr.org/e/services/newformat.html.
Acta Cryst. (2011). E67, 0 Files: e/bt5586/bt5586.3d e/bt5586/bt5586.sgml BT5586 QO
Manohar et al. IU-116/59(17)8 1113/21(12)8 (50)
doi:10.1107/S1600536811032788
BT5586 PROOFS
E:QO:2011:67:1:0:0–0
organic compounds 1
Acta Crystallographica Section E
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Structure Reports Online
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ISSN 1600-5368
= 1.08 mm1 T = 293 K 0.20 0.20 0.20 mm Is this OK?
˚ c = 12.6240 (9) A ˚3 V = 7158.9 (7) A Z = 16 Mo K radiation
Data collection
6
Xcalibur, Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) Tmin = 0.978, Tmax = 0.984
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1,7,8,9,10,10-Hexachloro-4-(thiophen-2ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8ene-3,5-dione R. Manohar,a M. Harikrishna,b C. R. Ramanathan,b M. SureshKumarc and K. Gunasekarana* a
CAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India, bDepartment of Chemistry, Pondicherry University, Pondicherry 605014, India, and cCentre for Bioinformatics, Pondicherry University, Pondicherry 605014, India Correspondence e-mail:
[email protected] Received 21 July 2011; accepted 12 August 2011
64 65 66 67 68
R[F 2 > 2(F 2)] = 0.037 wR(F 2) = 0.075 S = 0.82 4156 reflections
217 parameters H-atom parameters constrained ˚ 3 max = 0.31 e A ˚ 3 min = 0.31 e A
69 70 71 72 73
Table 1
74
˚ , ). Hydrogen-bond geometry (A
C2—H2 O2 C6—H6 O2i i
˚; Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.003 A R factor = 0.037; wR factor = 0.075; data-to-parameter ratio = 19.2.
63
Refinement
D—H A
75
D—H
H A
D A
D—H A
0.98 0.98
2.54 2.51
3.064 (3) 3.042 (3)
113 114
78 79
Symmetry code: (i) y 14; x þ 74; z 14.
80
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
CRR is grateful to the DST–FIST single-crystal X-ray facility of the Department of Chemistry, Pondicherry University, Pondicherry.
For the biological activity of cyclic imides, see: Duarte et al. (2006); Nakamura et al. (2006); Stefan´ska et al. (2010). Scheme: ugly bond angle at thiophene ring
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Experimental
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Crystal data
48
C14H7Cl6NO2S Mr = 465.97
49
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5586).
Tetragonal, I41 =a ˚ a = 23.8136 (10) A
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References
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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).
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8488 measured reflections 4156 independent reflections 2283 reflections with I > 2(I) Rint = 0.032
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Duarte, F. S., Andrade, E. S., Vieira, R. A., Uieara, M., de Nunes, R. J. & Lima, T. C. M. (2006). Bioorg. Med. Chem. 14, 5397–5401. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Nakamura, T., Noguchi, T., Kobayashi, H., Miyachi, H. & Hashimoto, Y. (2006). Chem. Pharm. Bull. 54, 1709–1714. Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Stefan´ska, J., Bielenica, A., Struga, M., Tyski, S., Kossakowski, J., Colla, P. L., Tamburini, E. & Loddo, R. (2010). Ann. Microbiol. 60, 151–155.
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Acta Cryst. (2011). E67, 0 Files: e/bt5586/bt5586.3d e/bt5586/bt5586.sgml BT5586 QO
Manohar et al. IU-116/59(17)8 1113/21(12)8 (50)
BT5586 PROOFS
E:QO:2011:67:1:0:0–0
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Article No.: E113278-BT5586
VAT No. GB 161 9034 76 Title of article
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
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