N-(4,6-Dimethylpyrimidin-2-yl)-4-(oxolan-2- ylamino)benzenesulfonamide

Author Arman, Hadi D., Kaulgud, Trupta, Tiekink, Edward R. T., Young, David

Published 2009

Journal Title Acta Crystallographica. Section E: Structure Reports Online

DOI https://doi.org/10.1107/S1600536809043347

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Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Editors: W.T. A. Harrison, J. Simpson and M. Weil

N-(4,6-Dimethylpyrimidin-2-yl)-4-(oxolan-2- ylamino)benzenesulfonamide

Hadi D. Arman, Trupta Kaulgud, Edward R. T. Tiekink and David J. Young

Acta Cryst. (2009). E65, o2851

This open-access article is distributed under the terms of the Creative Commons Attribution Licence http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

ISSN 1600-5368 Acta Crystallographica Section E

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Acta Cryst. (2009). E65, o2851 Arman et al. · C16H20N4O3S organic compounds

= Acta Crystallographica Section E Monoclinic, P21 c Z =4 Structure Reports a = 10.291 (5) A˚ Mo K radiation b = 9.592 (4) A˚ = 0.22 mm1 Online c = 17.196 (8) A˚ T =98K ISSN 1600-5368 = 106.445 (10) 0.35 0.21 0.11 mm V = 1628.0 (13) A˚ 3 N-(4,6-Dimethylpyrimidin-2-yl)-4- Data collection Rigaku Saturn724 diffractometer 11164 measured reflections (oxolan-2-ylamino)benzenesulfonamide Absorption correction: multi-scan 3749 independent reflections (ABSCOR; Higashi, 1995) 3341 reflections with I >2(I) T = 0.761, T = 1.000 R = 0.046 Hadi D. Arman,a Trupta Kaulgud,a Edward R. T. Tiekinkb* min max int c and David J. Young Refinement 2 2 a R[F >2 (F )] = 0.057 2 restraints Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, wR(F 2) = 0.137 H-atom parameters constrained San Antonio, Texas 78249-0698, USA, bDepartment of Chemistry, University of ˚ 3 S = 1.10 Ámax = 0.60 e A c ˚ 3 Malaya, 50603 Kuala Lumpur, Malaysia, and School of Biomolecular and Physical 3749 reflections Ámin = 0.39 e A Sciences, Nathan, Griffith University, Queensland 4111, Australia 225 parameters Correspondence e-mail: [email protected]

Received 20 October 2009; accepted 21 October 2009 Table 1 Hydrogen-bond geometry (A˚ , ). Key indicators: single-crystal X-ray study; T = 98 K; mean (C–C) = 0.004 A˚; R factor = 0.057; wR factor = 0.137; data-to-parameter ratio = 16.7. D—HAD—H HADAD—HA

N3—H3nO3i 0.88 1.98 2.854 (3) 174 N4—H4nN2ii 0.88 2.22 3.086 (3) 167 The title compound, C16H20N4O3S, adopts an l-shaped conformation, as seen by the dihedral angle of 76.93 (7) Symmetry codes: (i) x; y 1; z; (ii) x; y þ 1; z. formed between the two aromatic rings. The most notable CrystalClear feature of the crystal packing is the formation of N—HO Data collection: (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve and N—HN hydrogen bonds that lead to supramolecular structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine chains orientated along the b axis. structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material Related literature for publication: SHELXL97. For background to the co-crystallization of active pharma- The Queensland Department of Employment, Economic ceutical agents, see: Shan & Zaworotko (2008). For back- Development and Innovation is thanked for an International ground to sulfa drugs, see: Caira (2007); Nishimori et al. Fellowship to DJY. (2009). For the synthesis, see: Fructos et al. (2006); Kemnitz et al. (1998). For related studies on co-crystal formation, see: Supplementary data and figures for this paper are available from the Broker & Tiekink (2008); Broker et al. (2008). IUCr electronic archives (Reference: HB5159).

References Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Broker, G. A., Bettens, R. P.A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887. Broker, G. A. & Tiekink, E. R. T. (2008). CrystEngComm, 9, 1096–1109. Caira, M. R. (2007). Mol. Pharm. 4, 310–316. Fructos, M. R., Trofimenko, S., Mar Dı´az-Requejo, M. & Pe´rez, P. J. (2006). J. Am. Chem. Soc. 128, 11784–11791. Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Kemnitz, C. R., Karney, W. L. & Borden, W. T. (1998). J. Am. Chem. Soc. 120, 3499–3503. Nishimori, I., Minakuchi, T., Vullo, D., Scozzafava, A., Innocenti, A. & Supuran, C. T. (2009). J. Med. Chem. 52, 3116–3120. Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA. Shan, N. & Zaworotko, M. J. (2008). Drug Discovery Today, 13, 440–446. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Experimental Crystal data

C16H20N4O3S Mr = 348.42

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