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Volume 69 
Part 11 
Pages o1646-o1647  
November 2013  

Received 10 September 2013
Accepted 11 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.003 Å
R = 0.020
wR = 0.051
Data-to-parameter ratio = 17.7
Details
Open access

(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-5-methyl­tetra­hydro­furan-3,4-diol

aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and bInstitut für Neurowissenschaften und Medizin, Nuklearchemie (INM-5), Forschungszentrum Jülich GmbH, D-52428 Jülich, Germany
Correspondence e-mail: ulrich.floerke@upb.de

The mol­ecular structure of the title compound, C11H13IN4O3, shows a ribo­furanos­yl-pyrrolo O-C-N-C torsion angle of 59.1 (3)°, with the central C-N bond length being 1.446 (3) Å. The C-I bond length is 2.072 (2) Å. The amino group is coplanar with the attached aromatic ring [C-N-C-N torsion angle = -178.8 (2)°] and forms an intra­molecular N-H...I hydrogen bond. In the crystal, O-H...N and N-H...O hydrogen bonds link the mol­ecules into puckered layers parallel to (001). These layers are bound to each other by secondary I...O inter­actions [3.2250 (17) Å], forming a three-dimensional framework.

Related literature

For background to the use of marine natural products as therapeutic agents, see: Kazlauskas et al. (1983[Kazlauskas, R., Muphy, P. T., Wells, R. J., Baird-Lambert, J. A. & Jamieson, D. D. (1983). Aust. J. Chem. 36, 165-170.]); Mitchell et al. (1996[Mitchell, S. S., Pomerantz, S. C., Conception, G. P. & Ireland, C. M. (1996). J. Nat. Prod. 59, 1000-1001.]); Wiesner et al. (1999[Wiesner, J. B., Ugarkar, B. G., Castellino, A. J., Barankiewicz, J., Dumas, D. P., Gruber, H. E., Foster, A. C. & Erion, M. D. (1999). J. Pharmacol. Exp. Ther. 289, 1669-1677.]); Ugarkar et al. (2000[Ugarkar, B. G., DaRe, J. M., Kopcho, J. J., Browne, C. E., Schanzer, J. M., Wiesner, J. B. & Erion, M. D. (2000). J. Med. Chem. 43, 2883-2893.]); Song et al. (2011[Song, Y., Ding, H. X., Dou, Y. H., Yang, R. C., Sun, Q., Xiao, Q. & Ju, Y. (2011). Synthesis, 9, 1442-1446.]). For the structures of related compounds, see: Seela et al. (1996[Seela, F., Zulauf, M., Rosemeyer, H. & Reuter, H. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 2373-2376.], 1999[Seela, F., Zulauf, M., Reuter, H. & Kastner, G. (1999). Acta Cryst. C55, 1560-1562.], 2008[Seela, F., Ming, X., Budow, S., Eickmeier, H. & Reuter, H. (2008). Acta Cryst. C64, o293-o295.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13IN4O3

  • Mr = 376.15

  • Orthorhombic, P 21 21 21

  • a = 4.9164 (2) Å

  • b = 14.6490 (5) Å

  • c = 18.0130 (6) Å

  • V = 1297.30 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.48 mm-1

  • T = 130 K

  • 0.49 × 0.08 × 0.08 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.376, Tmax = 0.826

  • 12307 measured reflections

  • 3103 independent reflections

  • 3056 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.020

  • wR(F2) = 0.051

  • S = 1.06

  • 3103 reflections

  • 175 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.05 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1274 Friedel pairs

  • Absolute structure parameter: -0.015 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N2i 0.84 1.94 2.759 (3) 165
O3-H3...N1ii 0.84 2.16 2.907 (3) 149
N4-H4A...O2iii 0.88 2.07 2.915 (3) 160
N4-H4B...I1 0.88 2.92 3.636 (2) 139
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KQ2009 ).


References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Kazlauskas, R., Muphy, P. T., Wells, R. J., Baird-Lambert, J. A. & Jamieson, D. D. (1983). Aust. J. Chem. 36, 165-170.  [CrossRef] [ChemPort]
Mitchell, S. S., Pomerantz, S. C., Conception, G. P. & Ireland, C. M. (1996). J. Nat. Prod. 59, 1000-1001.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Seela, F., Ming, X., Budow, S., Eickmeier, H. & Reuter, H. (2008). Acta Cryst. C64, o293-o295.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Seela, F., Zulauf, M., Reuter, H. & Kastner, G. (1999). Acta Cryst. C55, 1560-1562.  [CSD] [CrossRef] [IUCr Journals]
Seela, F., Zulauf, M., Rosemeyer, H. & Reuter, H. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 2373-2376.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Song, Y., Ding, H. X., Dou, Y. H., Yang, R. C., Sun, Q., Xiao, Q. & Ju, Y. (2011). Synthesis, 9, 1442-1446.
Ugarkar, B. G., DaRe, J. M., Kopcho, J. J., Browne, C. E., Schanzer, J. M., Wiesner, J. B. & Erion, M. D. (2000). J. Med. Chem. 43, 2883-2893.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Wiesner, J. B., Ugarkar, B. G., Castellino, A. J., Barankiewicz, J., Dumas, D. P., Gruber, H. E., Foster, A. C. & Erion, M. D. (1999). J. Pharmacol. Exp. Ther. 289, 1669-1677.  [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1646-o1647   [ doi:10.1107/S1600536813027931 ]

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