(IUCr) 5,7,9,10-Tetrahydro-5[beta],10[beta]-methano-3a[alpha],8a[alpha]-methylpropenocycloocta[1,2-c:5,6-c']dipyrazole-3,8(2H,4H)-dione monohydrate

Volume 64
Part 6
Page o1055
June 2008

Received 5 May 2008
Accepted 7 May 2008
Online 10 May 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.090
Data-to-parameter ratio = 11.8
Details

5,7,9,10-Tetrahydro-5,10-methano-3a,8a-methylpropenocycloocta[1,2-c:5,6-c']dipyrazole-3,8(2H,4H)-dione monohydrate

Djamal Djaidi,^a Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney, Australia 2052
Correspondence e-mail: m.scudder@unsw.edu.au

The racemic title compound, C₁₅H₁₆N₄O₂·H₂O, crystallizes as a hydrogen-bonded layer structure incorporating the solvent water molecules. Within the layers, there are three distinct hydrogen-bonding motifs which can be classified as R₂²(8), R₄²(8) and R₄⁴(12).

Related literature

For related literature, see: Chan et al. (2008); Yue et al. (1997, 2000, 2007). For hydrogen-bonding analysis, see: Etter (1990).

Experimental

Crystal data

C₁₅H₁₆N₄O₂·H₂O
M_r = 302.3
Triclinic, $[P \overline 1]$
a = 6.478 (1) Å
b = 8.157 (1) Å
c = 14.812 (2) Å
= 85.412 (9)°
= 88.369 (8)°
= 67.089 (11)°
V = 718.6 (2) Å³
Z = 2
Cu K radiation
= 0.82 mm^-1
T = 294 K
0.30 × 0.25 × 0.22 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
2695 measured reflections
2695 independent reflections
2365 reflections with I > 2(I)
1 standard reflections frequency: 30 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.089
S = 1.64
2357 reflections
200 parameters
H-atom parameters not refined
_max = 0.34 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-HN2OWⁱ	1.00	1.83	2.763 (3)	154
N4-HN4O2ⁱⁱ	1.00	2.00	2.858 (2)	143
OW-H1OWO1	1.00	1.85	2.844 (2)	169
OW-H2OWO1ⁱⁱⁱ	1.00	1.81	2.796 (2)	169
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y, -z; (iii) -x, -y+2, -z+1.

Data collection: CAD-4 (Schagen et al., 1989); cell refinement: CAD-4; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (CrystalMaker Software, 2005); software used to prepare material for publication: local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2269 ).

Acknowledgements

This research was supported by the Australian Research Council.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Chan, I. Y. H., Bishop, R., Craig, D. C., Scudder, M. L. & Yue, W. (2008). Acta Cryst. E64, o841.
CrystalMaker Software (2005). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. www.CrystalMaker.co.uk.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Rae, A. D. (2000). RAELS. Australian National University, Canberra.
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Enraf-Nonius, Delft, The Netherlands.
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2000). Tetrahedron, 56, 6667-6673.
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2007). Acta Cryst. E63, o4689.
Yue, W., Bishop, R., Scudder, M. L. & Craig, D. C. (1997). J. Chem. Soc., Perkin Trans. 1, pp. 2937-2946.

organic compounds