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Volume 69 
Part 2 
Pages o288-o289  
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) = 0.003 Å
R = 0.029
wR = 0.074
Data-to-parameter ratio = 16.9
Details
Open access

rac-5-Bromo-N-benzylisatincreatinine ethanol monosolvate

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

In the title compound [systematic name: rac-1-benzyl-5-bromo-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C19H17BrN4O3·C2H5OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s. deviations from the mean plane of 0.0276 (14) Å. The phenyl ring of the benzyl group makes a dihedral angle with the mean plane of the isatin ring of 87.40 (5)° and the dihedral angle between the imidazole and isatin rings is 58.56 (7)°. In the crystal, molecules are linked into two-dimensional pleated-sheet networks in the ac plane formed by O-H...O, N-H...O and O-H...N hydrogen bonds; within these sheets there are R44(10) rings that involve three molecules of the title compound and a single ethanol solvent molecule. In addition, there are [pi]-[pi] interactions between inversion-related benzyl groups, with an interplanar spacing of 3.444 (3) Å.

Related literature

Background information on the biological importance of isatins has been given by Pandeya et al. (2005[Pandeya, S. N., Smitha, S., Jyoti, M. & Sridhar, S. K. (2005). Acta Pharm. 55, 27-46.]), and by Vine et al. (2007[Vine, K. L., Locke, J. M., Ranson, M., Benkendorff, K., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.]). 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

  • C19H17BrN4O3·C2H6O

  • Mr = 475.34

  • Monoclinic, P 21 /n

  • a = 7.8384 (16) Å

  • b = 24.553 (5) Å

  • c = 10.936 (2) Å

  • [beta] = 99.54 (3)°

  • V = 2075.6 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.02 mm-1

  • T = 90 K

  • 0.20 × 0.15 × 0.10 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan [SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and XABS2 (Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.])] Tmin = 0.689, Tmax = 0.824

  • 41507 measured reflections

  • 4752 independent reflections

  • 4147 reflections with I > 2[sigma](I)

  • Rint = 0.038
Refinement

  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.074

  • S = 1.05

  • 4752 reflections

  • 282 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 1.19 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O9-H9...O1Si 0.84 1.87 2.694 (2) 169
N13-H13A...O11ii 0.81 (2) 2.00 (2) 2.811 (2) 171 (2)
N13-H13B...O9iii 0.82 (2) 2.36 (2) 2.933 (2) 128 (2)
N13-H13B...O1iii 0.82 (2) 2.46 (2) 3.158 (2) 144 (2)
O1S-H1S...N12 0.84 1.91 2.745 (2) 174
Symmetry codes: (i) x+1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: SHELXL97 and local procedures.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5279 ).

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA140409. We thank Dr S. Parkin, University of Kentucky, for X-ray crystallographic services.

References

Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pandeya, S. N., Smitha, S., Jyoti, M. & Sridhar, S. K. (2005). Acta Pharm. 55, 27-46.  [PubMed] [ChemPort]
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [ISI] [details]
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]
Tang, Y., Chen, G., Zhang, J. & Chen, S. (2009). Acta Cryst. E65, o2597.  [CrossRef] [details]
Vine, K. L., Locke, J. M., Ranson, M., Benkendorff, K., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.  [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2013). E69, o288-o289   [ doi:10.1107/S160053681300038X ]

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