(E)-N′-(2,4,6-Trihydroxy­benzyl­idene)isonicotinohydrazide sesquihydrate

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Loh, W.-S.; Fun, H.-K.

doi:10.1107/S1600536810014959

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1202-o1203

https://doi.org/10.1107/S1600536810014959

Open

access

(E)-N′-(2,4,6-Trihydroxybenzylidene)isonicotinohydrazide sesquihydrate

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Wan-Sin Loh ^b § and Hoong-Kun Fun ^b ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 17 March 2010; accepted 23 April 2010; online 28 April 2010)

In the title compound, C₁₃H₁₁N₃O₄·1.5H₂O, the pyridine ring forms a dihedral angle of 1.50 (6)° with the benzene ring. An intramolecular O—H⋯N hydrogen bond forms a six-membered ring with an S(6) ring motif. In the crystal structure, one water molecule is disordered over two positions around an inversion centre with site-occupancy factors of 0.5. Intermolecular O—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds consolidate the structure into a three dimensional network. A π–π stacking interaction with a centroid–centroid distance of 3.5949 (7) Å is also present.

Related literature

For biological applications of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ). For related structures, see: Naveenkumar et al. (2009 ); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010 ); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010 ); Shi (2005 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the synthesis, see: Lourenco et al. (2008 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₄·1.5H₂O
M_r = 300.27
Monoclinic, P 2₁ /c
a = 8.4639 (1) Å
b = 13.2279 (2) Å
c = 13.4363 (2) Å
β = 120.037 (1)°
V = 1302.30 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.48 × 0.46 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.944, T_max = 0.977
14912 measured reflections
3795 independent reflections
3090 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.139
S = 1.05
3795 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4	0.76	2.05	2.8134 (13)	176
O1W—H2W1⋯O2ⁱ	0.82	2.09	2.8886 (14)	165
O2W—H1W2⋯O4ⁱⁱ	0.83	2.06	2.864 (3)	162
O2W—H2W2⋯O4	0.83	2.17	2.844 (3)	139
N2—H1N2⋯O1Wⁱⁱⁱ	0.87 (2)	1.99 (2)	2.8548 (13)	170 (3)
O1—H1O1⋯N1	0.87 (3)	1.78 (2)	2.5696 (15)	149 (2)
O2—H1O2⋯N3^iv	0.87 (3)	1.82 (3)	2.6470 (14)	158 (3)
O3—H1O3⋯O1^v	0.72 (3)	2.16 (3)	2.7579 (15)	142 (3)
O3—H1O3⋯O2W^vi	0.72 (3)	2.40 (3)	2.970 (2)	138 (3)
C4—H4A⋯O2W^vi	0.984 (18)	2.290 (17)	3.135 (2)	143.3 (14)
C7—H7A⋯O1Wⁱⁱⁱ	0.993 (19)	2.539 (19)	3.3185 (16)	135.2 (14)
C10—H10A⋯O1Wⁱⁱⁱ	0.996 (18)	2.355 (18)	3.3063 (17)	159.4 (13)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+2, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810014959/is2532sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014959/is2532Isup2.hkl

checkCIF report

Comment top

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden & Barry, 2000). Schiff bases have attracted much attention because of their biological activity (Kahwa et al., 1986). As a part of a current work of synthesis of (E)-N'-(substituted-benzylidene)isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), contains one (E)-N'-(2,4,6-trihydroxybenzylidene) isonicotinohydrazide and one and a half water molecules. The partially-occupied water molecule (O2W, H1W2, H2W2) is disordered across a crystallographic inversion center. The pyridine ring (C9–C11/N3/C12/C13) is essentially planar with a maximum deviation of 0.006 (1) Å at atom C9 and forms a dihedral angle of 1.51 (6)° with the benzene ring (C1–C6). An intramolecular O1—H1O1···N1 hydrogen bond forms a six-membered ring with an S(6) ring motif (Bernstein et al., 1995). The bond lengths are within normal values (Allen et al., 1987) and are comparable to those observed for closely related structures (Naveenkumar et al., 2009; Naveenkumar, Sadikun, Ibrahim, Quah & Fun, 2010; Naveenkumar, Sadikun, Ibrahim, Yeap & Fun, 2010; Shi, 2005).

In the crystal packing (Fig. 2), intermolecular O1W—H1W1···O4, O1W—H2W1···O2, O2W—H1W2···O4, O2W—H2W2···O4, N2—H1N2···O1W, O2—H1O2···N3, O3—H1O3···O1, O3—H1O3···O2W, C4—H4A···O2W, C7—H7A···O1W and C10—H10A···O1W hydrogen bonds (Table 1) consolidate the structure into a three dimensional network. The crystal structure is further stabilized by π–π stacking interactions involving the pyridine (Cg1) and benzene (Cg2) rings with a centroid–centroid distance of 3.5949 (7) Å (symmetry code = -1+x, y, z).

Related literature top

For biological applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar et al. (2009); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010); Shi (2005). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the synthesis, see: Lourenco et al. (2008). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The isoniazid derivative was prepared following the procedure by Lourenco et al. (2008). (E)-N'-(2,4,6-trihydroxybenzylidene)isonicotinohydrazide hydrate was prepared by reaction between the 2,4,6-trihydroxy benzaldehyde (1.0 eq) with isoniazid (1.0 eq) in ethanol/water. After stirring for 1 to 3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue after being purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. Colourless single crystals suitable for X-ray analysis were obtained by recrystallization with methanol.

Structure description top

For biological applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the biological activity of Schiff bases, see: Kahwa et al. (1986). For related structures, see: Naveenkumar et al. (2009); Naveenkumar, Sadikun, Ibrahim, Quah & Fun (2010); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2010); Shi (2005). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the synthesis, see: Lourenco et al. (2008). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Dashed line indicates the intramolecular hydrogen bond. Atom O2WA was generated by symmetry code -x+1, -y+1, -z.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Intermolecular interactions are shown as dashed lines. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(E)-N'-(2,4,6-Trihydroxybenzylidene)isonicotinohydrazide sesquihydrate top

Crystal data top

C₁₃H₁₁N₃O₄·1.5H₂O	F(000) = 628
M_r = 300.27	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6535 reflections
a = 8.4639 (1) Å	θ = 2.3–30.0°
b = 13.2279 (2) Å	µ = 0.12 mm⁻¹
c = 13.4363 (2) Å	T = 100 K
β = 120.037 (1)°	Block, brown
V = 1302.30 (3) Å³	0.48 × 0.46 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3795 independent reflections
Radiation source: fine-focus sealed tube	3090 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→9
T_min = 0.944, T_max = 0.977	k = −16→18
14912 measured reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.086P)² + 0.1988P] where P = (F_o² + 2F_c²)/3
3795 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₄·1.5H₂O	V = 1302.30 (3) Å³
M_r = 300.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4639 (1) Å	µ = 0.12 mm⁻¹
b = 13.2279 (2) Å	T = 100 K
c = 13.4363 (2) Å	0.48 × 0.46 × 0.19 mm
β = 120.037 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3795 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3090 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.977	R_int = 0.025
14912 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.38 e Å⁻³
3795 reflections	Δρ_min = −0.38 e Å⁻³
244 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > σ(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	Occ. (<1)
O1W	0.52172 (13)	0.55973 (6)	0.31668 (9)	0.0306 (2)
H1W1	0.4784	0.5243	0.2649	0.046*
H2W1	0.5174	0.5182	0.3604	0.046*
O2W	0.4201 (3)	0.47492 (16)	−0.05523 (19)	0.0394 (5)	0.50
H1W2	0.4991	0.5075	−0.0609	0.059*	0.50
H2W2	0.4565	0.4623	0.0132	0.059*	0.50
O2	1.48904 (12)	0.38723 (8)	0.43699 (8)	0.0293 (2)
O3	1.05057 (15)	0.11707 (7)	0.32046 (9)	0.0306 (2)
O4	0.34364 (13)	0.43232 (6)	0.12386 (8)	0.0280 (2)
C1	0.99950 (15)	0.38970 (8)	0.31225 (10)	0.0201 (2)
C2	1.17860 (16)	0.42239 (9)	0.35826 (11)	0.0232 (3)
C3	1.31689 (15)	0.35102 (9)	0.39166 (10)	0.0209 (2)
C4	1.27822 (16)	0.24762 (9)	0.37910 (10)	0.0216 (2)
C5	1.09857 (16)	0.21590 (8)	0.33268 (9)	0.0193 (2)
C6	0.95461 (15)	0.28593 (8)	0.29762 (9)	0.0169 (2)
C7	0.76941 (16)	0.25025 (8)	0.25037 (9)	0.0188 (2)
C8	0.32356 (16)	0.34043 (8)	0.13119 (10)	0.0192 (2)
C9	0.13728 (15)	0.29709 (8)	0.08915 (9)	0.0168 (2)
C10	0.09871 (15)	0.19404 (8)	0.07857 (10)	0.0185 (2)
C11	−0.08123 (16)	0.16375 (9)	0.03428 (10)	0.0204 (2)
C12	−0.18124 (17)	0.32760 (10)	0.01401 (11)	0.0247 (3)
C13	−0.00643 (17)	0.36473 (9)	0.05683 (11)	0.0229 (2)
N1	0.63769 (13)	0.31447 (7)	0.21721 (8)	0.0204 (2)
N2	0.46426 (13)	0.27539 (8)	0.17637 (8)	0.0190 (2)
N3	−0.22009 (14)	0.22835 (8)	0.00221 (8)	0.0223 (2)
O1	0.86777 (13)	0.46088 (7)	0.28226 (10)	0.0343 (3)
H2A	1.208 (2)	0.4987 (14)	0.3659 (15)	0.040 (4)*
H4A	1.371 (3)	0.1941 (13)	0.4038 (14)	0.034 (4)*
H7A	0.751 (2)	0.1759 (14)	0.2465 (14)	0.038 (5)*
H10A	0.191 (2)	0.1392 (12)	0.1008 (14)	0.030 (4)*
H11A	−0.111 (2)	0.0914 (12)	0.0240 (14)	0.031 (4)*
H12A	−0.275 (3)	0.3696 (13)	−0.0081 (15)	0.038 (4)*
H13A	0.015 (3)	0.4324 (14)	0.0657 (15)	0.040 (5)*
H1N2	0.456 (3)	0.2097 (15)	0.1781 (16)	0.042 (5)*
H1O1	0.763 (3)	0.4296 (17)	0.2534 (18)	0.067 (7)*
H1O2	1.567 (4)	0.3379 (19)	0.460 (2)	0.082 (8)*
H1O3	1.115 (4)	0.083 (2)	0.318 (2)	0.091 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0255 (5)	0.0203 (4)	0.0424 (6)	−0.0037 (3)	0.0141 (4)	−0.0053 (4)
O2W	0.0331 (11)	0.0438 (12)	0.0422 (12)	−0.0075 (9)	0.0195 (10)	−0.0002 (9)
O2	0.0091 (4)	0.0362 (5)	0.0367 (5)	−0.0001 (3)	0.0070 (4)	−0.0033 (4)
O3	0.0389 (6)	0.0164 (4)	0.0446 (6)	0.0028 (4)	0.0270 (5)	−0.0006 (4)
O4	0.0243 (5)	0.0181 (4)	0.0412 (5)	−0.0043 (3)	0.0159 (4)	0.0009 (3)
C1	0.0129 (5)	0.0171 (5)	0.0280 (6)	0.0008 (4)	0.0084 (5)	−0.0002 (4)
C2	0.0152 (5)	0.0197 (5)	0.0339 (6)	−0.0024 (4)	0.0116 (5)	−0.0053 (4)
C3	0.0104 (5)	0.0295 (6)	0.0202 (5)	−0.0005 (4)	0.0056 (4)	−0.0026 (4)
C4	0.0172 (6)	0.0261 (6)	0.0211 (5)	0.0076 (4)	0.0092 (5)	0.0031 (4)
C5	0.0219 (6)	0.0181 (5)	0.0193 (5)	0.0026 (4)	0.0114 (5)	0.0009 (4)
C6	0.0137 (5)	0.0174 (5)	0.0169 (5)	−0.0011 (4)	0.0057 (4)	−0.0002 (4)
C7	0.0178 (5)	0.0200 (5)	0.0170 (5)	−0.0042 (4)	0.0076 (4)	−0.0005 (4)
C8	0.0161 (5)	0.0204 (5)	0.0195 (5)	−0.0037 (4)	0.0078 (4)	−0.0004 (4)
C9	0.0139 (5)	0.0194 (5)	0.0163 (5)	−0.0016 (4)	0.0068 (4)	0.0007 (4)
C10	0.0132 (5)	0.0200 (5)	0.0201 (5)	−0.0012 (4)	0.0067 (4)	0.0003 (4)
C11	0.0146 (5)	0.0242 (6)	0.0206 (5)	−0.0041 (4)	0.0073 (4)	−0.0024 (4)
C12	0.0169 (6)	0.0289 (6)	0.0277 (6)	0.0051 (5)	0.0109 (5)	0.0052 (5)
C13	0.0209 (6)	0.0202 (5)	0.0278 (6)	0.0017 (4)	0.0124 (5)	0.0035 (4)
N1	0.0117 (4)	0.0254 (5)	0.0200 (5)	−0.0053 (4)	0.0048 (4)	0.0015 (4)
N2	0.0114 (4)	0.0199 (5)	0.0215 (5)	−0.0052 (3)	0.0052 (4)	0.0005 (3)
N3	0.0135 (4)	0.0324 (5)	0.0195 (5)	−0.0008 (4)	0.0073 (4)	0.0004 (4)
O1	0.0166 (5)	0.0175 (4)	0.0695 (7)	0.0026 (3)	0.0221 (5)	0.0055 (4)

Geometric parameters (Å, º) top

O1W—H1W1	0.7630	C6—C7	1.4445 (15)
O1W—H2W1	0.8193	C7—N1	1.2908 (15)
O2W—O2Wⁱ	1.569 (4)	C7—H7A	0.994 (18)
O2W—H1W2	0.8308	C8—N2	1.3428 (15)
O2W—H2W2	0.8278	C8—C9	1.4973 (15)
O2—C3	1.3546 (14)	C9—C10	1.3923 (15)
O2—H1O2	0.87 (3)	C9—C13	1.3928 (16)
O3—C5	1.3544 (14)	C10—C11	1.3881 (15)
O3—H1O3	0.72 (3)	C10—H10A	0.998 (17)
O4—C8	1.2380 (13)	C11—N3	1.3380 (15)
C1—O1	1.3573 (14)	C11—H11A	0.981 (16)
C1—C2	1.3888 (16)	C12—N3	1.3434 (16)
C1—C6	1.4115 (15)	C12—C13	1.3817 (17)
C2—C3	1.3918 (16)	C12—H12A	0.892 (19)
C2—H2A	1.033 (18)	C13—H13A	0.908 (18)
C3—C4	1.3968 (17)	N1—N2	1.3845 (13)
C4—C5	1.3884 (17)	N2—H1N2	0.87 (2)
C4—H4A	0.984 (18)	O1—H1O1	0.87 (3)
C5—C6	1.4107 (15)

H1W1—O1W—H2W1	93.9	C6—C7—H7A	117.1 (10)
O2Wⁱ—O2W—H1W2	61.0	O4—C8—N2	122.62 (11)
O2Wⁱ—O2W—H2W2	50.9	O4—C8—C9	120.43 (10)
H1W2—O2W—H2W2	109.7	N2—C8—C9	116.95 (9)
C3—O2—H1O2	110.3 (18)	C10—C9—C13	118.27 (11)
C5—O3—H1O3	115 (2)	C10—C9—C8	124.21 (10)
O1—C1—C2	117.87 (10)	C13—C9—C8	117.51 (10)
O1—C1—C6	120.62 (10)	C11—C10—C9	118.50 (11)
C2—C1—C6	121.50 (10)	C11—C10—H10A	116.6 (9)
C1—C2—C3	119.12 (10)	C9—C10—H10A	124.9 (9)
C1—C2—H2A	120.4 (10)	N3—C11—C10	123.51 (11)
C3—C2—H2A	120.4 (10)	N3—C11—H11A	117.2 (10)
O2—C3—C2	116.54 (11)	C10—C11—H11A	119.3 (10)
O2—C3—C4	122.33 (11)	N3—C12—C13	122.98 (11)
C2—C3—C4	121.13 (11)	N3—C12—H12A	116.4 (11)
C5—C4—C3	119.20 (10)	C13—C12—H12A	120.7 (11)
C5—C4—H4A	116.4 (10)	C12—C13—C9	119.18 (11)
C3—C4—H4A	124.4 (10)	C12—C13—H13A	120.3 (12)
O3—C5—C4	122.73 (11)	C9—C13—H13A	120.5 (12)
O3—C5—C6	115.90 (10)	C7—N1—N2	116.89 (10)
C4—C5—C6	121.35 (10)	C8—N2—N1	117.66 (10)
C5—C6—C1	117.70 (10)	C8—N2—H1N2	126.0 (13)
C5—C6—C7	119.87 (10)	N1—N2—H1N2	116.2 (13)
C1—C6—C7	122.43 (10)	C11—N3—C12	117.55 (10)
N1—C7—C6	119.76 (10)	C1—O1—H1O1	107.7 (15)
N1—C7—H7A	123.1 (10)

O1—C1—C2—C3	178.88 (11)	C1—C6—C7—N1	1.73 (16)
C6—C1—C2—C3	−0.63 (19)	O4—C8—C9—C10	170.29 (11)
C1—C2—C3—O2	−179.37 (10)	N2—C8—C9—C10	−9.79 (16)
C1—C2—C3—C4	0.32 (19)	O4—C8—C9—C13	−8.54 (16)
O2—C3—C4—C5	179.54 (10)	N2—C8—C9—C13	171.38 (10)
C2—C3—C4—C5	−0.15 (18)	C13—C9—C10—C11	1.26 (16)
C3—C4—C5—O3	−178.26 (10)	C8—C9—C10—C11	−177.57 (10)
C3—C4—C5—C6	0.26 (17)	C9—C10—C11—N3	−0.76 (17)
O3—C5—C6—C1	178.08 (10)	N3—C12—C13—C9	0.27 (19)
C4—C5—C6—C1	−0.54 (16)	C10—C9—C13—C12	−1.03 (17)
O3—C5—C6—C7	−0.98 (15)	C8—C9—C13—C12	177.87 (10)
C4—C5—C6—C7	−179.60 (10)	C6—C7—N1—N2	−177.87 (9)
O1—C1—C6—C5	−178.77 (10)	O4—C8—N2—N1	0.86 (17)
C2—C1—C6—C5	0.73 (17)	C9—C8—N2—N1	−179.06 (9)
O1—C1—C6—C7	0.27 (17)	C7—N1—N2—C8	−173.68 (10)
C2—C1—C6—C7	179.76 (11)	C10—C11—N3—C12	−0.01 (17)
C5—C6—C7—N1	−179.26 (10)	C13—C12—N3—C11	0.26 (18)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4	0.76	2.05	2.8134 (13)	176
O1W—H2W1···O2ⁱⁱ	0.82	2.09	2.8886 (14)	165
O2W—H1W2···O4ⁱ	0.83	2.06	2.864 (3)	162
O2W—H2W2···O4	0.83	2.17	2.844 (3)	139
N2—H1N2···O1Wⁱⁱⁱ	0.87 (2)	1.99 (2)	2.8548 (13)	170 (3)
O1—H1O1···N1	0.87 (3)	1.78 (2)	2.5696 (15)	149 (2)
O2—H1O2···N3^iv	0.87 (3)	1.82 (3)	2.6470 (14)	158 (3)
O3—H1O3···O1^v	0.72 (3)	2.16 (3)	2.7579 (15)	142 (3)
O3—H1O3···O2W^vi	0.72 (3)	2.40 (3)	2.970 (2)	138 (3)
C4—H4A···O2W^vi	0.984 (18)	2.290 (17)	3.135 (2)	143.3 (14)
C7—H7A···O1Wⁱⁱⁱ	0.993 (19)	2.539 (19)	3.3185 (16)	135.2 (14)
C10—H10A···O1Wⁱⁱⁱ	0.996 (18)	2.355 (18)	3.3063 (17)	159.4 (13)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+2, −y+1/2, z+1/2; (v) −x+2, y−1/2, −z+1/2; (vi) x+1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₄·1.5H₂O
M_r	300.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.4639 (1), 13.2279 (2), 13.4363 (2)
β (°)	120.037 (1)
V (Å³)	1302.30 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.48 × 0.46 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.944, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	14912, 3795, 3090
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.139, 1.05
No. of reflections	3795
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4	0.7600	2.0500	2.8134 (13)	176.00
O1W—H2W1···O2ⁱ	0.8200	2.0900	2.8886 (14)	165.00
O2W—H1W2···O4ⁱⁱ	0.8300	2.0600	2.864 (3)	162.00
O2W—H2W2···O4	0.8300	2.1700	2.844 (3)	139.00
N2—H1N2···O1Wⁱⁱⁱ	0.87 (2)	1.99 (2)	2.8548 (13)	170 (3)
O1—H1O1···N1	0.87 (3)	1.78 (2)	2.5696 (15)	149 (2)
O2—H1O2···N3^iv	0.87 (3)	1.82 (3)	2.6470 (14)	158 (3)
O3—H1O3···O1^v	0.72 (3)	2.16 (3)	2.7579 (15)	142 (3)
O3—H1O3···O2W^vi	0.72 (3)	2.40 (3)	2.970 (2)	138 (3)
C4—H4A···O2W^vi	0.984 (18)	2.290 (17)	3.135 (2)	143.3 (14)
C7—H7A···O1Wⁱⁱⁱ	0.993 (19)	2.539 (19)	3.3185 (16)	135.2 (14)
C10—H10A···O1Wⁱⁱⁱ	0.996 (18)	2.355 (18)	3.3063 (17)	159.4 (13)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+2, −y+1/2, z+1/2; (v) −x+2, y−1/2, −z+1/2; (vi) x+1, −y+1/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: amirin@usm.my.

§Thomson Reuters ResearcherID: C-7581-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (1001/PFARMASI/815005). HKF and WSL thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). HSNK and WSL are grateful for the award of USM fellowships for financial assistance.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Janin, Y. L. (2007). Bioorg. Med. Chem. 15, 2479–2513. Web of Science CrossRef PubMed CAS Google Scholar
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Lourenco, M. C. S., Ferreira, M. L., de Souza, M. V. N., Peralta, M. A., Vasconcelos, T. R. A. & Henriques, M. G. M. O. (2008). Eur. J. Med. Chem. 43, 1344–1347. Web of Science CrossRef PubMed CAS Google Scholar
Maccari, R., Ottana, R. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 2509–2513. Web of Science CrossRef PubMed CAS Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Loh, W.-S. & Fun, H.-K. (2009). Acta Cryst. E65, o2540–o2541. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o291. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o579. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, J. (2005). Acta Cryst. E61, o3933–o3934. Web of Science CSD CrossRef IUCr Journals Google Scholar
Slayden, R. A. & Barry, C. E. (2000). Microbes Infect. 2, 659–669. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar