organic compounds
Acta Crystallographica Section E b = 5.2908 (4) A˚ Z =2 Structure Reports c = 21.8464 (18) A˚ Cu K radiation = 92.833 (6) = 0.89 mm 1 Online = 90.315 (7) T = 173 K ISSN 1600-5368 = 96.222 (7) 0.42 0.22 0.12 mm V = 575.67 (8) A˚ 3 4-[(4-Acetylphenyl)amino]-2-methyl- Data collection Agilent Eos Gemini diffractometer 3374 measured reflections idene-4-oxobutanoic acid Absorption correction: multi-scan 2168 independent reflections (CrysAlis PRO and CrysAlis 1934 reflections with I >2 (I) RED; Agilent, 2012) R = 0.025 B. Narayana,a Prakash S. Nayak,b Balladka K. Sarojinic and int Tmin = 0.756, Tmax = 1.000 Jerry P. Jasinskid* Refinement a Department of Studies in Chemistry, Mangalore University, Mangaloagangotri R[F 2 >2 (F 2)] = 0.048 H atoms treated by a mixture of b 574 199, India, Department of Studies in Chemistry, Mangalore University, wR(F 2) = 0.134 independent and constrained Mangalagangotri 574 199, India, cDepartment of Studies in Chemistry, Industrial S = 1.05 refinement ˚ 3 Chemistry Section, Mangalore University, Mangalagangotri 574 199, India, and 2168 reflections Á max = 0.31 e A d ˚ 3 Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435- 176 parameters Á min = 0.29 e A 2001, USA Correspondence e-mail: [email protected] Table 1 Received 19 May 2014; accepted 30 May 2014 Hydrogen-bond geometry (A˚ , ).
Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.002 A˚; D—H AD—H H AD AD—H A R factor = 0.048; wR factor = 0.134; data-to-parameter ratio = 12.3. O3—H3 O2i 0.97 (5) 1.66 (5) 2.6262 (17) 174 (4) N1—H1 O1ii 0.88 2.29 3.1039 (17) 154 C5—H5B O2iii 1.00 (3) 2.48 (3) 3.434 (2) 160 (2) ii In the title compound, C13H13NO4, the N—C( O) bond C7—H7 O1 0.95 2.56 3.254 (2) 130 length of 1.354 (2) A˚ is indicative of amide-type resonance. C13—H13A O4iv 0.98 2.50 3.465 (2) 167 The dihedral angle between the mean planes of the benzene Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x; y þ 1; z; (iii) x; y; z þ 1; (iv) ring and oxoamine group is 36.4 (3) , while the mean plane of x; y 1; z. the 2-methylidene group is inclined by 84.2 (01) from that of Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: the oxoamine group. In the crystal, classical O—H O CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); hydrogen bonds formed by the carboxylic acid groups and program(s) used to solve structure: SUPERFLIP (Palatinus et al., weak N—H O weak interactions formed by the amide 2012); program(s) used to refine structure: SHELXL2012 (Sheldrick, groups and supported by weak C—H O interactions 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software between the 2-methylidene, phenyl and acetyl groups with used to prepare material for publication: OLEX2. the carboxylic acid, oxoamine and acetyl O atoms, together link the molecules into dimeric chains along [010]. The O— BN thanks the UGC for financial assistance through a BSR 2 H O hydrogen bonds form R2(8) graph-set motifs. one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and DST–PURSE financial assistance. JPJ acknowledges the NSF–MRI program Related literature (grant No. CHE-1039027) for funds to purchase the X-ray For the pharmacological activity of amide derivatives, see: diffractometer. Galanakis et al. (2004); Kumar & Knaus (1993); Ban et al. (1998); Ukrainets et al. (2006), Lesyk & Zimenkovsky (2004); Supporting information for this paper is available from the IUCr Gududuru et al. (2004). For related structures, see: Nayak et al. electronic archives (Reference: ZL2589). (2013a,b). For standard bond lengths, see: Allen et al. (1987). References Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. Ban, M., Taguchi, H., Katushima, T., Takahashi, M., Shinoda, K., Watanabe, A. & Tominaga, T. (1998). Bioorg. Med. Chem. 6, 1069–1076. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Experimental Galanakis, D., Kourounakis, A. P., Tsiakitzis, K. C., Doulgkeris, C., Rekka, E. A., Gavalas, A., Kravaritou, C., Christos, C. & Kourounakis, P. N. (2004). Crystal data Bioorg. Med. Chem. Lett. 14, 3639–3643. Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. C13H13NO4 Triclinic, P1 Chem. Lett. 14, 5289–5293. ˚ Mr = 247.24 a = 5.0164 (5) A Kumar, P. & Knaus, E. E. (1993). Eur. J. Med. Chem. 28, 881–885. o752 Narayana et al. doi:10.1107/S1600536814012562 Acta Cryst. (2014). E70, o752–o753 organic compounds
Lesyk, R. & Zimenkovsky, B. (2004). Curr. Org. Chem. 8, 1547–1578. Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575– Nayak, P. S., Narayana, B., Yathirajan, H. S., Gerber, T., Brecht, B. van & Betz, 580. R. (2013a). Acta Cryst. E69, o83. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Nayak, P. S., Narayana, B., Yathirajan, H. S., Gerber, T., van Brecht, B. & Betz, Ukrainets, I. V., Sidorenko, L. V., Petrushovo, L. A. & Gorokhova, O. V. R. (2013a). Acta Cryst. E69, o83. (2006). Chem. Heterocycl. Comput. 42, 64–69.