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Volume 69 
Part 2 
Pages o290-o291  
February 2013  

Received 11 December 2012
Accepted 4 January 2013
Online 26 January 2013

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Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.104
Data-to-parameter ratio = 12.6
Details
Open access

rac-N-Benzylisatincreatinine (unknown solvate)

Narsimha Reddy Penthalaa and Peter A. Crooksa*

aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA
Correspondence e-mail: pacrooks@uams.edu

The title compound, C19H18N4O3 [systematic name: (RS)-1-benzyl-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzylisatin with creatinine in the presence of sodium acetate in acetic acid. The r.m.s. deviation of the isatin ring system is 0.033 Å. The benzyl group is disordered over two orientations, with refined occupancies of 0.847 (7) and 0.153 (7). The dihedral angles between the isatin ring system and the benzene ring (major disorder component) and the imidazole ring are 82.82 (7) and 51.31 (3)°, respectively, In the crystal, molecules are linked into (001) sheets by N-H...O and O-H...N hydrogen bonds, which incorporate R22(9) ring motifs. The crystal was grown from mixed solvents (ethanol, methanol and possibly also ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninterpretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. The formula mass and density do not take account of the solvent.

Related literature

For details on the development of isatin derivatives as anticancer agents, see: Penthala et al. (2010a[Penthala, N. R., Reddy, T. R. Y., Nikhil, R. M. & Crooks, P. A. (2010a). Bioorg. Med. Chem. Lett. 20, 4468-4471.],b[Penthala, N. R., Reddy, T. R. Y., Nikhil, R. M. & Crooks, P. A. (2010b). Bioorg. Med. Chem. Lett. 20, 591-593.]). For similar structures, see: Tang et al. (2009[Tang, Y., Chen, G., Zhang, J. & Chen, S. (2009). Acta Cryst. E65, o2597.]); Penthala et al. (2009a[Penthala, N. R., Reddy, T. R. Y., Parkin, S. & Crooks, P. A. (2009a). Acta Cryst. E65, o552.],b[Penthala, N. R., Reddy, T. R. Y., Parkin, S. & Crooks, P. A. (2009b). Acta Cryst. E65, o2909-o2910.]).

[Scheme 1]

Experimental

Crystal data

  • C19H18N4O3

  • Mr = 350.37

  • Orthorhombic, P b c a

  • a = 13.4466 (2) Å

  • b = 10.6921 (2) Å

  • c = 27.2057 (5) Å

  • V = 3911.43 (12) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.68 mm-1

  • T = 90 K

  • 0.12 × 0.10 × 0.04 mm
Data collection

  • Bruker X8 Proteum CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.911, Tmax = 0.973

  • 55165 measured reflections

  • 3602 independent reflections

  • 3344 reflections with I > 2[sigma](I)

  • Rint = 0.043
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.104

  • S = 1.04

  • 3602 reflections

  • 287 parameters

  • 222 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O9-H9...N12i 0.84 1.97 2.8065 (13) 175
N13-H13A...O11ii 0.88 2.24 2.9321 (13) 135
N13-H13B...O1iii 0.88 1.97 2.8410 (14) 173
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELX97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7013 ).

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant RO1 CA140409.

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Penthala, N. R., Reddy, T. R. Y., Nikhil, R. M. & Crooks, P. A. (2010a). Bioorg. Med. Chem. Lett. 20, 4468-4471.  [CrossRef] [ChemPort] [PubMed]
Penthala, N. R., Reddy, T. R. Y., Nikhil, R. M. & Crooks, P. A. (2010b). Bioorg. Med. Chem. Lett. 20, 591-593.
Penthala, N. R., Reddy, T. R. Y., Parkin, S. & Crooks, P. A. (2009a). Acta Cryst. E65, o552.  [CSD] [CrossRef] [details]
Penthala, N. R., Reddy, T. R. Y., Parkin, S. & Crooks, P. A. (2009b). Acta Cryst. E65, o2909-o2910.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tang, Y., Chen, G., Zhang, J. & Chen, S. (2009). Acta Cryst. E65, o2597.  [CrossRef] [details]

Acta Cryst (2013). E69, o290-o291   [ doi:10.1107/S1600536813000378 ]

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