electronic reprint (2,4,6-Trinitrophenyl)guanidine Graham Smith, Urs D. Wermuth and Jonathan M. White Editors: W. Clegg and D. G.

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1 Acta Crystallographica Section E Structure Reports Online ISSN Editors: W. Clegg and D. G. Watson (2,4,6-Trinitrophenyl)guanidine Graham Smith, Urs D. Wermuth and Jonathan M. White Copyright International Union of Crystallography Author(s) of this paper may load this reprint on their own web site or institutional repository provided that this cover page is retained. Republication of this article or its storage in electronic databases other than as specified above is not permitted without prior permission in writing from the IUCr. For further information see Acta Cryst. (2007). E63, o3759 Smith et al. ffl C 7H 6 N 6 O 6

2 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN (2,4,6-Trinitrophenyl)guanidine Graham Smith, a * Urs D. Wermuth b and Jonathan M. White c a School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, b School of Biomolecular and Physical Sciences, Griffith University, Nathan, Queensland 4111, Australia, and c BIO-21 Molecular Science and Biotechnology, University of Melbourne, Parkville, Victoria 3052, Australia Correspondence g.smith@qut.edu.au Received 1 August 2007; accepted 2 August 2007 = (2) V = (11) Å 3 Z =2 Mo K radiation Data collection Bruker SMART CCD area-detector diffractometer Absorption correction: none 2614 measured reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 188 parameters Table 1 Hydrogen-bond geometry (Å, ). = 0.16 mm 1 T = 130 (2) K mm 1739 independent reflections 1344 reflections with I > 2(I) R int = H atoms treated by a mixture of independent and constrained refinement max = 0.22 e Å 3 min = 0.21 e Å 3 Key indicators: single-crystal X-ray study; T = 130 K; mean (C C) = Å; R factor = 0.038; wr factor = 0.083; data-to-parameter ratio = 9.2. (2,4,6-Trinitrophenyl)guanidine (picrylguanidine), C 7 H 6 N 6 O 6, from the reaction of picrylsulfonic acid with guanidine carbonate, forms a three-dimensional framework structure through extensive hydrogen-bonding interactions, extending the centrosymmetric cyclic R 2 2 (16) dimer association which includes duplex R 2 2 (8) guanidine N HO nitro interactions. The guanidine substituent chain has an endo [Ph N C(NH 2 ) 2 ] bond sequence rather than the less sterically encumbered exo [Ph NH C NH(NH 2 )] sequence of the tautomeric form. As a result, there is significant bond-angle distortion about C( N ) of the aromatic ring. Related literature For related literature, see: Crocker & Matthews (1911); Goldfarb (1966); Lundgren (1972); Lundgren & Tellgren (1974); Russell & Ward (1997); Smith et al. (2006, 2007). D HA D H HA DA D HA N71 H71AO41 i 0.85 (2) 2.28 (2) (3) (18) N71 H71BO21 ii 0.89 (3) 2.27 (3) (2) 173 (2) N72 H72AO42 iii 0.91 (3) 2.38 (3) (3) 147 (2) N72 H72AO62 iv 0.91 (3) 2.37 (3) (3) 132 (2) N72 H72BO22 ii (19) (19) (2) 168 (2) C5 H5O61 v (3) 159 Symmetry codes: (i) x þ 2; y; z þ 2; (ii) x þ 1; y; z þ 1; (iii) x þ 2; y þ 1; z þ 2; (iv) x þ 2; y þ 1; z þ 1; (v) x þ 3; y þ 1; z þ 2. Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON. The authors acknowledge financial support from the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Biomolecular and Physical Sciences, Griffith University and the School of Chemistry, University of Melbourne. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2462). Experimental Crystal data C 7 H 6 N 6 O 6 M r = Triclinic, P1 a = (10) Å b = (10) Å c = (12) Å = (3) = (2) References Bruker (1999). SAINT. Version Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2000). SMART. Version Bruker AXS Inc., Madison, Wisconsin, USA. Crocker, J. C. & Matthews, F. (1911). J. Chem. Soc. pp Goldfarb, A. R. (1966). Biochem. 5, Lundgren, J.-O. (1972). Acta Cryst. B28, Lundgren, J.-O. & Tellgren, R. (1974). Acta Cryst. B30, Russell, V. A. & Ward, M. D. (1997). J. Mater. Chem. 7, Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Smith, G., Wermuth, U. D. & Healy, P. C. (2006). Acta Cryst. E62, o5510 o5512. Smith, G., Wermuth, U. D. & White, J. M. (2007). Unpublished results. Spek, A. L. (2003). J. Appl. Cryst. 36, Acta Cryst. (2007). E63, o3759 doi: /s # 2007 International Union of Crystallography o3759

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