N′-Acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide dihydrate

Dolzhenko, A.V.; Dolzhenko, A.V.; Tan, G.K.; Koh, L.L.; Pastorin, G.

doi:10.1107/S1600536810015357

Volume 66
Part 5
Pages o1209-o1210
May 2010

Received 22 April 2010
Accepted 26 April 2010
Online 30 April 2010

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.141
Data-to-parameter ratio = 13.9
Details

N'-Acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide dihydrate

Anna V. Dolzhenko,^a ^* Anton V. Dolzhenko,^a Geok Kheng Tan,^b Lip Lin Koh ^b and Giorgia Pastorin ^a

^aDepartment of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore, and ^bDepartment of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
Correspondence e-mail: phada@nus.edu.sg

In the title compound, C₇H₁₂N₆O·2H₂O, the Z configuration of the hydrazone fragment is stabilized by an intramolecular N-HN hydrogen bond involving one of the amino groups. In the crystal structure, the hydrazonamide molecules are connected via intermolecular N-HO=C hydrogen bonds, forming C(7) chains running along [010]. The chains form sheets parallel to the ( $[\overline{1}]$ 01). The chains are cross-linked by water molecules to form a three-dimensional hydrogen-bonded network.

Related literature

For bioactive pyrazoles, see: Elguero et al. (2002); Lamberth (2007). For the use of pyrazoles as synthons in heterocyclic chemistry, see: Schenone et al. (2007); Dolzhenko et al. (2008). For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000); Halcrow (2009). For the crystal structures of related 5-amino-1H-pyrazole-4-carboxylic acid derivatives, see: Zia-ur-Rehman et al. (2008, 2009); Caruso et al. (2009). For the crystal structure of N'-acetyl-2-phenylethanehydrazonamide, see: Ianelli et al. (2001). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental

Crystal data

C₇H₁₂N₆O·2H₂O
M_r = 232.26
Triclinic, $[P \overline 1]$
a = 7.5496 (9) Å
b = 7.6208 (9) Å
c = 11.2518 (13) Å
= 102.645 (2)°
= 101.440 (2)°
= 110.810 (2)°
V = 562.75 (11) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 223 K
0.45 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.953, T_max = 0.989
3963 measured reflections
2548 independent reflections
2174 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.141
S = 1.05
2548 reflections
183 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2W-H4WN1ⁱ	0.87 (3)	2.04 (3)	2.884 (2)	162 (3)
O2W-H3WO1	0.86 (3)	2.11 (3)	2.885 (2)	150 (3)
O1W-H2WO2Wⁱⁱ	0.89 (3)	1.93 (3)	2.824 (2)	175 (3)
O1W-H1WN5	0.81 (3)	2.24 (3)	2.982 (2)	153 (3)
N6-H6NO1Wⁱⁱⁱ	0.84 (2)	2.07 (2)	2.905 (2)	177 (2)
N4-H42O1Wⁱⁱⁱ	0.88 (2)	2.14 (3)	2.995 (2)	165 (2)
N4-H41O1^iv	0.81 (2)	2.08 (2)	2.874 (2)	169 (2)
N3-H32N5	0.86 (2)	2.18 (2)	2.791 (2)	128 (2)
N3-H31O2W^v	0.83 (2)	2.27 (2)	3.082 (2)	163 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x, y-1, z; (v) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5086 ).

Acknowledgements

This work was supported by the National Medical Research Council, Singapore (grant No. NMRC/NIG/0020/2008).

References

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Caruso, F., Raimondi, M. V., Daidone, G., Pettinari, C. & Rossi, M. (2009). Acta Cryst. E65, o2173.
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2008). Heterocycles, 75, 1575-1622.
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organic compounds