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

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1209-o1210

https://doi.org/10.1107/S1600536810015357

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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

(Received 22 April 2010; accepted 26 April 2010; online 30 April 2010)

In the title compound, C₇H₁₂N₆O·2H₂O, the Z configuration of the hydrazone fragment is stabilized by an intramolecular N—H⋯N hydrogen bond involving one of the amino groups. In the crystal structure, the hydrazonamide molecules are connected via intermolecular N—H⋯O=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
α = 102.645 (2)°
β = 101.440 (2)°
γ = 110.810 (2)°
V = 562.75 (11) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(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
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H4W⋯N1ⁱ	0.87 (3)	2.04 (3)	2.884 (2)	162 (3)
O2W—H3W⋯O1	0.86 (3)	2.11 (3)	2.885 (2)	150 (3)
O1W—H2W⋯O2Wⁱⁱ	0.89 (3)	1.93 (3)	2.824 (2)	175 (3)
O1W—H1W⋯N5	0.81 (3)	2.24 (3)	2.982 (2)	153 (3)
N6—H6N⋯O1Wⁱⁱⁱ	0.84 (2)	2.07 (2)	2.905 (2)	177 (2)
N4—H42⋯O1Wⁱⁱⁱ	0.88 (2)	2.14 (3)	2.995 (2)	165 (2)
N4—H41⋯O1^iv	0.81 (2)	2.08 (2)	2.874 (2)	169 (2)
N3—H32⋯N5	0.86 (2)	2.18 (2)	2.791 (2)	128 (2)
N3—H31⋯O2W^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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015357/ci5086sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015357/ci5086Isup2.hkl

checkCIF report

Comment top

Pyrazoles have been well recognized as valuable ligands in metal-organic chemistry (Mukherjee, 2000; Halcrow, 2009). Pyrazoles also possess useful agricultural (Lamberth, 2007) and pharmacological (Elguero et al., 2002) properties and serve as synthons for other pyrazolo fused bioactive heterocycles (Schenone et al., 2007; Dolzhenko et al., 2008).

Herein, we report molecular and crystal structure of N'-acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide (Figs. 1 and 2). The compound can exist in two tautomeric forms, namely hydrazonamide and imidohydrazide (Fig. 3). The hydrazonamide tautomer can also exhibit (E-Z) isomerism by inversion of configuration of the hydrazono C═N linkage. We found that the compound crystallizes as a N'-acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide tautomer. Similarly to previously reported N'-acetyl-2-phenylethanehydrazonamide (Ianelli et al., 2001), the hydrazonamide group of N'-acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide adopts (Z)-configuration. This configuration is stabilized by the intramolecular N(3)H···N5═C5 hydrogen bonding between the amino group and the hydrazone N5 atom, generating an S(6) graph-set motif (Bernstein et al., 1995). Similar NH···O═C interactions were reported for the structurally related derivatives of 5-amino-1H-pyrazole-4-carboxylic acid (Zia-ur-Rehman et al., 2008; Zia-ur-Rehman et al., 2009; Caruso et al., 2009). Planarity of the molecule is affected by slight twisting of the acetyl group [C5—N5—N6—C6 torsion angle is 170.14 (16)°].

In the crystal, the hydrazonamide molecules are arranged to form sheets parallel to the (101) (Fig. 2). In the sheets, atom N4 of one molecule is involved in a intermolecular N—H···O═C interaction with the carbonyl atom O1 of adjacent molecule making C(7) chains along the [010] direction. The water molecules further stabilize packing by formation of the intermolecular hydrogen bond network (Fig. 2 and Table 1).

Related literature top

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 top

N'-Acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide was prepared by treatment of ethyl N-(4-cyano-1-methyl-1H-pyrazol-5-yl)acetimidate with 3 eq. of hydrazine hydrate (40%) in ethanol. Detail procedure with proposed mechanism will be reported elsewhere. Single crystals suitable for the crystallographic analysis were grown by recrystallization from ethanol, m.p. 513 K.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of N'-acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide dihydrate showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound, viewed along the a axis.
	Fig. 3. Hydrazonamide-imidohydrazide tautomerism in N'-acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide

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

Crystal data top

C₇H₁₂N₆O·2H₂O	Z = 2
M_r = 232.26	F(000) = 248
Triclinic, P1	D_x = 1.371 Mg m⁻³
Hall symbol: -P 1	Melting point: 513 K
a = 7.5496 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6208 (9) Å	Cell parameters from 1515 reflections
c = 11.2518 (13) Å	θ = 3.0–27.5°
α = 102.645 (2)°	µ = 0.11 mm⁻¹
β = 101.440 (2)°	T = 223 K
γ = 110.810 (2)°	Rod, colourless
V = 562.75 (11) Å³	0.45 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2548 independent reflections
Radiation source: fine-focus sealed tube	2174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
T_min = 0.953, T_max = 0.989	k = −9→9
3963 measured reflections	l = −14→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0711P)² + 0.1961P] where P = (F_o² + 2F_c²)/3
2548 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₇H₁₂N₆O·2H₂O	γ = 110.810 (2)°
M_r = 232.26	V = 562.75 (11) Å³
Triclinic, P1	Z = 2
a = 7.5496 (9) Å	Mo Kα radiation
b = 7.6208 (9) Å	µ = 0.11 mm⁻¹
c = 11.2518 (13) Å	T = 223 K
α = 102.645 (2)°	0.45 × 0.12 × 0.10 mm
β = 101.440 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.31 e Å⁻³
2548 reflections	Δρ_min = −0.26 e Å⁻³
183 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3615 (2)	0.89463 (19)	0.14623 (12)	0.0421 (4)
N1	0.7337 (2)	0.3950 (2)	0.48625 (14)	0.0306 (4)
N2	0.7791 (2)	0.5933 (2)	0.51428 (13)	0.0264 (3)
N3	0.7066 (3)	0.8221 (2)	0.42298 (16)	0.0302 (4)
H31	0.748 (3)	0.907 (3)	0.495 (2)	0.036 (6)*
H32	0.613 (3)	0.821 (3)	0.365 (2)	0.039 (6)*
N4	0.3308 (2)	0.2471 (2)	0.11287 (15)	0.0297 (4)
H41	0.350 (3)	0.158 (3)	0.132 (2)	0.032 (5)*
H42	0.260 (3)	0.223 (3)	0.034 (2)	0.040 (6)*
N5	0.4378 (2)	0.5945 (2)	0.18078 (13)	0.0294 (4)
N6	0.3198 (2)	0.5816 (2)	0.06398 (13)	0.0267 (3)
H6N	0.269 (3)	0.479 (3)	0.000 (2)	0.037 (6)*
C1	0.6808 (2)	0.6344 (2)	0.41838 (15)	0.0239 (4)
C2	0.5664 (2)	0.4541 (2)	0.32050 (15)	0.0236 (4)
C3	0.6068 (3)	0.3143 (3)	0.37018 (16)	0.0272 (4)
H3	0.5496	0.1780	0.3256	0.033*
C4	0.9204 (3)	0.7328 (3)	0.63443 (17)	0.0359 (4)
H4A	1.0140	0.8443	0.6188	0.054*
H4C	0.9916	0.6687	0.6766	0.054*
H4D	0.8504	0.7791	0.6886	0.054*
C5	0.4374 (2)	0.4304 (2)	0.19753 (15)	0.0225 (3)
C6	0.2965 (3)	0.7431 (3)	0.05365 (16)	0.0278 (4)
C7	0.1873 (3)	0.7318 (3)	−0.07661 (17)	0.0354 (4)
H7A	0.0729	0.7603	−0.0721	0.053*
H7B	0.1431	0.6000	−0.1353	0.053*
H7C	0.2751	0.8278	−0.1066	0.053*
O1W	0.8443 (2)	0.7733 (2)	0.15574 (13)	0.0380 (4)
H1W	0.752 (5)	0.757 (4)	0.186 (3)	0.069 (9)*
H2W	0.949 (5)	0.780 (4)	0.213 (3)	0.065 (8)*
O2W	0.1806 (2)	0.8169 (2)	0.34309 (14)	0.0393 (4)
H3W	0.253 (4)	0.812 (4)	0.294 (3)	0.064 (9)*
H4W	0.189 (4)	0.731 (4)	0.381 (3)	0.060 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0739 (10)	0.0235 (7)	0.0262 (7)	0.0259 (7)	0.0028 (7)	0.0046 (5)
N1	0.0382 (8)	0.0292 (8)	0.0260 (8)	0.0170 (7)	0.0052 (6)	0.0107 (6)
N2	0.0311 (7)	0.0255 (7)	0.0195 (7)	0.0118 (6)	0.0023 (6)	0.0060 (6)
N3	0.0413 (9)	0.0219 (7)	0.0218 (8)	0.0130 (7)	0.0021 (7)	0.0032 (6)
N4	0.0436 (9)	0.0173 (7)	0.0228 (8)	0.0136 (6)	−0.0018 (6)	0.0053 (6)
N5	0.0403 (8)	0.0219 (7)	0.0197 (7)	0.0141 (6)	−0.0034 (6)	0.0043 (6)
N6	0.0375 (8)	0.0195 (7)	0.0174 (7)	0.0128 (6)	−0.0022 (6)	0.0029 (6)
C1	0.0268 (8)	0.0265 (8)	0.0186 (7)	0.0119 (7)	0.0058 (6)	0.0071 (6)
C2	0.0286 (8)	0.0225 (8)	0.0199 (8)	0.0119 (6)	0.0046 (6)	0.0072 (6)
C3	0.0342 (9)	0.0228 (8)	0.0241 (8)	0.0138 (7)	0.0037 (7)	0.0076 (6)
C4	0.0374 (10)	0.0406 (11)	0.0206 (8)	0.0142 (8)	−0.0003 (7)	0.0043 (8)
C5	0.0274 (8)	0.0211 (8)	0.0188 (7)	0.0114 (6)	0.0045 (6)	0.0061 (6)
C6	0.0353 (9)	0.0264 (8)	0.0217 (8)	0.0143 (7)	0.0048 (7)	0.0085 (7)
C7	0.0447 (11)	0.0370 (10)	0.0273 (9)	0.0227 (9)	0.0026 (8)	0.0136 (8)
O1W	0.0406 (8)	0.0395 (8)	0.0236 (7)	0.0125 (6)	0.0021 (6)	0.0044 (6)
O2W	0.0518 (9)	0.0414 (8)	0.0299 (7)	0.0253 (7)	0.0082 (7)	0.0145 (6)

Geometric parameters (Å, º) top

O1—C6	1.236 (2)	C1—C2	1.401 (2)
N1—C3	1.317 (2)	C2—C3	1.402 (2)
N1—N2	1.372 (2)	C2—C5	1.459 (2)
N2—C1	1.344 (2)	C3—H3	0.94
N2—C4	1.445 (2)	C4—H4A	0.97
N3—C1	1.362 (2)	C4—H4C	0.97
N3—H31	0.83 (2)	C4—H4D	0.97
N3—H32	0.86 (2)	C6—C7	1.500 (2)
N4—C5	1.350 (2)	C7—H7A	0.97
N4—H41	0.81 (2)	C7—H7B	0.97
N4—H42	0.88 (2)	C7—H7C	0.97
N5—C5	1.303 (2)	O1W—H1W	0.81 (3)
N5—N6	1.3953 (19)	O1W—H2W	0.89 (3)
N6—C6	1.330 (2)	O2W—H3W	0.86 (3)
N6—H6N	0.84 (2)	O2W—H4W	0.87 (3)

C3—N1—N2	104.63 (14)	C2—C3—H3	123.7
C1—N2—N1	112.10 (14)	N2—C4—H4A	109.5
C1—N2—C4	127.04 (15)	N2—C4—H4C	109.5
N1—N2—C4	120.85 (14)	H4A—C4—H4C	109.5
C1—N3—H31	117.5 (15)	N2—C4—H4D	109.5
C1—N3—H32	110.8 (16)	H4A—C4—H4D	109.5
H31—N3—H32	119 (2)	H4C—C4—H4D	109.5
C5—N4—H41	116.7 (15)	N5—C5—N4	126.14 (15)
C5—N4—H42	123.9 (15)	N5—C5—C2	114.92 (14)
H41—N4—H42	118 (2)	N4—C5—C2	118.95 (15)
C5—N5—N6	117.52 (14)	O1—C6—N6	121.90 (15)
C6—N6—N5	117.50 (14)	O1—C6—C7	121.68 (16)
C6—N6—H6N	119.6 (15)	N6—C6—C7	116.42 (15)
N5—N6—H6N	122.8 (15)	C6—C7—H7A	109.5
N2—C1—N3	122.61 (15)	C6—C7—H7B	109.5
N2—C1—C2	106.59 (14)	H7A—C7—H7B	109.5
N3—C1—C2	130.72 (15)	C6—C7—H7C	109.5
C1—C2—C3	104.15 (14)	H7A—C7—H7C	109.5
C1—C2—C5	125.02 (15)	H7B—C7—H7C	109.5
C3—C2—C5	130.83 (15)	H1W—O1W—H2W	110 (3)
N1—C3—C2	112.53 (15)	H3W—O2W—H4W	103 (3)
N1—C3—H3	123.7

C3—N1—N2—C1	0.66 (19)	N2—N1—C3—C2	−0.1 (2)
C3—N1—N2—C4	−178.36 (16)	C1—C2—C3—N1	−0.5 (2)
C5—N5—N6—C6	170.14 (16)	C5—C2—C3—N1	179.83 (17)
N1—N2—C1—N3	−177.99 (15)	N6—N5—C5—N4	−1.0 (3)
C4—N2—C1—N3	1.0 (3)	N6—N5—C5—C2	178.89 (14)
N1—N2—C1—C2	−0.95 (19)	C1—C2—C5—N5	1.9 (2)
C4—N2—C1—C2	178.00 (16)	C3—C2—C5—N5	−178.43 (17)
N2—C1—C2—C3	0.82 (18)	C1—C2—C5—N4	−178.18 (16)
N3—C1—C2—C3	177.53 (18)	C3—C2—C5—N4	1.5 (3)
N2—C1—C2—C5	−179.44 (15)	N5—N6—C6—O1	−6.2 (3)
N3—C1—C2—C5	−2.7 (3)	N5—N6—C6—C7	173.75 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H4W···N1ⁱ	0.87 (3)	2.04 (3)	2.884 (2)	162 (3)
O2W—H3W···O1	0.86 (3)	2.11 (3)	2.885 (2)	150 (3)
O1W—H2W···O2Wⁱⁱ	0.89 (3)	1.93 (3)	2.824 (2)	175 (3)
O1W—H1W···N5	0.81 (3)	2.24 (3)	2.982 (2)	153 (3)
N6—H6N···O1Wⁱⁱⁱ	0.84 (2)	2.07 (2)	2.905 (2)	177 (2)
N4—H42···O1Wⁱⁱⁱ	0.88 (2)	2.14 (3)	2.995 (2)	165 (2)
N4—H41···O1^iv	0.81 (2)	2.08 (2)	2.874 (2)	169 (2)
N3—H32···N5	0.86 (2)	2.18 (2)	2.791 (2)	128 (2)
N3—H31···O2W^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.

Experimental details

Crystal data
Chemical formula	C₇H₁₂N₆O·2H₂O
M_r	232.26
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	7.5496 (9), 7.6208 (9), 11.2518 (13)
α, β, γ (°)	102.645 (2), 101.440 (2), 110.810 (2)
V (Å³)	562.75 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.953, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3963, 2548, 2174
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.141, 1.05
No. of reflections	2548
No. of parameters	183
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H4W···N1ⁱ	0.87 (3)	2.04 (3)	2.884 (2)	162 (3)
O2W—H3W···O1	0.86 (3)	2.11 (3)	2.885 (2)	150 (3)
O1W—H2W···O2Wⁱⁱ	0.89 (3)	1.93 (3)	2.824 (2)	175 (3)
O1W—H1W···N5	0.81 (3)	2.24 (3)	2.982 (2)	153 (3)
N6—H6N···O1Wⁱⁱⁱ	0.84 (2)	2.07 (2)	2.905 (2)	177 (2)
N4—H42···O1Wⁱⁱⁱ	0.88 (2)	2.14 (3)	2.995 (2)	165 (2)
N4—H41···O1^iv	0.81 (2)	2.08 (2)	2.874 (2)	169 (2)
N3—H32···N5	0.86 (2)	2.18 (2)	2.791 (2)	128 (2)
N3—H31···O2W^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.

Acknowledgements

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

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