(E)-N′-(2,3,4-Trihy­droxy­benzyl­idene)­isonicotinohydrazide dihydrate

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536810043965

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o3017-o3018

https://doi.org/10.1107/S1600536810043965

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(E)-N′-(2,3,4-Trihydroxybenzylidene)isonicotinohydrazide dihydrate

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Jia Hao Goh ^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 20 October 2010; accepted 27 October 2010; online 31 October 2010)

In the title isoniazid derivative, C₁₃H₁₁N₃O₄·2H₂O, the Schiff base molecule exists in an E configuration with respect to the acyclic C=N bond. An intramolecular O—H⋯N hydrogen bond forms a six-membered ring, producing an S(6) ring motif. The essentially planar pyridine ring [maximum deviation = 0.0119 (8) Å] is inclined at a dihedral angle of 7.30 (4)° with respect to the benzene ring. In the crystal, intermolecular O—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into two-dimensional arrays lying parallel to the (10 $[\overline{1}]$ ) plane. These arrays are further interconnected into a three-dimensional extended network via O—H⋯O and C—H⋯O hydrogen bonds. A weak intermolecular π–π interaction [centroid-to-centroid distance = 3.5627 (5) Å] is also observed.

Related literature

For general background to and applications of the title isoniazid derivative, see: Janin (2007 ); Kahwa et al. (1986 ); Maccari et al. (2005 ); Slayden & Barry (2000 ). For the preparation of the title compound, see: Lourenço et al. (2008 ). For closely related isoniazid structures, see: Naveenkumar et al. (2009 , 2010a ,b ,c ); Shi (2005 ). For hydrogen-bond ring motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₄·2H₂O
M_r = 309.28
Monoclinic, P 2₁ /c
a = 6.9504 (5) Å
b = 19.9077 (13) Å
c = 10.0930 (7) Å
β = 106.416 (2)°
V = 1339.60 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.35 × 0.18 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.959, T_max = 0.989
21520 measured reflections
5656 independent reflections
4668 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.03
5656 reflections
259 parameters
All H-atom parameters refined
Δρ_max = 0.50 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
O2—H1O2⋯N3	0.883 (18)	1.854 (18)	2.6561 (9)	150.1 (16)
O3—H1O3⋯N1ⁱ	0.869 (19)	1.835 (19)	2.6911 (10)	168.4 (18)
O4—H1O4⋯O1W	0.895 (18)	1.769 (18)	2.6559 (9)	170.5 (18)
N2—H1N2⋯O2Wⁱⁱ	0.890 (16)	2.132 (15)	2.9910 (9)	162.1 (14)
O1W—H1W1⋯O1ⁱⁱⁱ	0.926 (18)	1.880 (18)	2.7834 (9)	164.6 (16)
O1W—H2W1⋯O2W	0.837 (19)	2.077 (18)	2.8980 (11)	167.0 (18)
O2W—H1W2⋯O2^iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2⋯O4^v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A⋯O1^vi	0.922 (14)	2.575 (14)	3.2930 (11)	135.1 (11)
C7—H7A⋯O2Wⁱⁱ	0.988 (14)	2.347 (14)	3.2176 (10)	146.7 (12)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z-1; (iv) x, y, z-1; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) -x+2, -y+1, -z+3.

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/S1600536810043965/rz2508sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043965/rz2508Isup2.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 our current work on synthesis of (E)-N'-substituted isonicotinohydrazide derivatives, in this paper we present the crystal structure of the title compound.

The title isoniazid derivative comprises of a (E)-N'-(2,3,4-trihydroxybenzylidene)isonicotinohydrazide molecule and two water molecules of crystallization (Fig. 1). The Schiff base molecule exists in an E configuration with respect to the acyclic C7═N3 bond [C7═N3 = 1.2921 (10) Å; torsion angle N2—N3—C7—C8 = 178.85 (7)°]. An intramolecular O2—H1O2···N3 hydrogen bond (Table 1) generates a six-membered ring, producing an S(6) ring motifs (Bernstein et al., 1995). The pyridine ring with atom sequence C1/C2/N1/C3/C4/C5 is essentially planar, with a maximum deviation of 0.0119 (8) Å at atom C5. There is a slight inclination between the pyridine and benzene rings, as indicated by the dihedral angle formed of 7.30 (4)°. All bond lengths and angles are consistent to those observed in closely related isoniazid structures (Naveenkumar et al., 2009, 2010a,b,c; Shi, 2005).

In the crystal packing, water molecules play an extensive part in forming the hydrogen-bonded structure. Neighbouring molecules are linked into two-dimensional arrays parallel to the (101) plane (Fig. 2) by intermolecular O3—H1O3···N1, O4—H1O4···O1W, N2—H1N2···O2W, O1W—H1W1···O1, O2W—H2W2···O4 and C7—H7A···O2W hydrogen bonds (Table 1). These arrays are further interconnected by intermolecular O1W—H2W1···O2W, O2W—H1W2···O2 and C4—H4A···O1 hydrogen bonds (Table 1) into a three-dimensional extended structure (Fig. 3). Weak intermolecular π–π aromatic stacking interactions involving the pyridine and benzene rings [Cg1···Cg2 = 3.5627 (5) Å, symmetry code: -x + 2, -y + 1, -z + 2] stabilizing the crystal structure.

Related literature top

For general background to and applications of the title isoniazid derivative, see: Janin (2007); Kahwa et al. (1986); Maccari et al. (2005); Slayden & Barry (2000). For the preparation of the title compound, see: Lourenço et al. (2008). For closely related isoniazid structures, see: Naveenkumar et al. (2009, 2010a,b,c); Shi (2005). For hydrogen-bond ring motifs, see: Bernstein et al. (1995). 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 Lourenço et al., 2008. The title compound was prepared by the reaction between 2,3,4-trihydroxybenzaldehyde (1.0 eq) with isoniazid (1.0 eq) in ethanol/water. After stirring for 1–3 h at room temperature, the resulting mixture was concentrated under reduced pressure. The residue, purified by washing with cold ethanol and ethyl ether, afforded the pure derivative. The brown-coloured single crystals suitable for X-ray analysis were obtained by recrystallization with ethanol.

Structure description top

For general background to and applications of the title isoniazid derivative, see: Janin (2007); Kahwa et al. (1986); Maccari et al. (2005); Slayden & Barry (2000). For the preparation of the title compound, see: Lourenço et al. (2008). For closely related isoniazid structures, see: Naveenkumar et al. (2009, 2010a,b,c); Shi (2005). For hydrogen-bond ring motifs, see: Bernstein et al. (1995). 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 asymmetric unit of the title isoniazid derivative, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. Part of the crystal structure, viewed along the [101] direction, showing a hydrogen-bonded 2D array. Intermolecular hydrogen bonds are shown as dashed lines.
	Fig. 3. The crystal structure of the title derivative, viewed along the b axis, showing the 2D arrays being linked into a 3D extended network. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(2,3,4-Trihydroxybenzylidene)isonicotinohydrazide dihydrate top

Crystal data top

C₁₃H₁₁N₃O₄·2H₂O	F(000) = 648
M_r = 309.28	D_x = 1.534 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7532 reflections
a = 6.9504 (5) Å	θ = 2.9–34.5°
b = 19.9077 (13) Å	µ = 0.12 mm⁻¹
c = 10.0930 (7) Å	T = 100 K
β = 106.416 (2)°	Plate, brown
V = 1339.60 (16) Å³	0.35 × 0.18 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5656 independent reflections
Radiation source: fine-focus sealed tube	4668 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 34.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.959, T_max = 0.989	k = −31→31
21520 measured reflections	l = −16→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0651P)² + 0.2238P] where P = (F_o² + 2F_c²)/3
5656 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₄·2H₂O	V = 1339.60 (16) Å³
M_r = 309.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9504 (5) Å	µ = 0.12 mm⁻¹
b = 19.9077 (13) Å	T = 100 K
c = 10.0930 (7) Å	0.35 × 0.18 × 0.09 mm
β = 106.416 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5656 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4668 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.989	R_int = 0.031
21520 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	All H-atom parameters refined
S = 1.03	Δρ_max = 0.50 e Å⁻³
5656 reflections	Δρ_min = −0.26 e Å⁻³
259 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 > 2sigma(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	1.01608 (10)	0.51301 (3)	1.29712 (6)	0.01639 (12)
O2	0.67646 (10)	0.62875 (3)	0.99244 (6)	0.01723 (13)
O3	0.48628 (10)	0.72385 (3)	0.80029 (6)	0.01782 (13)
O4	0.29346 (10)	0.68845 (3)	0.54245 (6)	0.01504 (12)
N1	1.23127 (11)	0.28684 (4)	1.50037 (7)	0.01687 (14)
N2	0.86827 (10)	0.44582 (3)	1.11516 (6)	0.01251 (12)
N3	0.78423 (10)	0.50085 (3)	1.03671 (7)	0.01281 (12)
C1	1.05976 (13)	0.33042 (4)	1.27584 (8)	0.01494 (14)
C2	1.14706 (13)	0.27828 (4)	1.36485 (8)	0.01646 (15)
C3	1.22531 (14)	0.34874 (4)	1.55190 (8)	0.01760 (15)
C4	1.14150 (13)	0.40355 (4)	1.47177 (8)	0.01499 (14)
C5	1.05899 (11)	0.39475 (4)	1.32999 (7)	0.01165 (13)
C6	0.97938 (12)	0.45639 (4)	1.24693 (7)	0.01180 (13)
C7	0.68132 (12)	0.48824 (4)	0.91109 (8)	0.01247 (13)
C8	0.58229 (11)	0.54102 (3)	0.81860 (7)	0.01120 (13)
C9	0.58328 (11)	0.60855 (4)	0.85957 (7)	0.01149 (13)
C10	0.48749 (12)	0.65802 (4)	0.76616 (7)	0.01176 (13)
C11	0.38589 (11)	0.63908 (4)	0.63033 (7)	0.01128 (13)
C12	0.38052 (12)	0.57192 (4)	0.58943 (7)	0.01307 (13)
C13	0.47908 (12)	0.52365 (4)	0.68254 (7)	0.01302 (13)
O1W	0.13931 (13)	0.64535 (3)	0.28519 (7)	0.02289 (15)
O2W	0.30816 (11)	0.67273 (3)	0.05904 (7)	0.01959 (13)
H1O2	0.732 (3)	0.5922 (9)	1.0365 (17)	0.041 (4)*
H1O3	0.582 (3)	0.7387 (9)	0.8694 (18)	0.045 (5)*
H1O4	0.247 (3)	0.6695 (9)	0.4591 (19)	0.045 (5)*
H1N2	0.836 (2)	0.4055 (8)	1.0773 (15)	0.034 (4)*
H1A	1.001 (2)	0.3205 (7)	1.1767 (14)	0.023 (3)*
H2A	1.146 (2)	0.2338 (7)	1.3281 (14)	0.023 (3)*
H3A	1.282 (2)	0.3542 (6)	1.6527 (14)	0.021 (3)*
H4A	1.135 (2)	0.4445 (7)	1.5129 (14)	0.028 (3)*
H7A	0.665 (2)	0.4412 (7)	0.8788 (15)	0.029 (3)*
H12A	0.306 (2)	0.5605 (7)	0.4985 (13)	0.020 (3)*
H13A	0.479 (2)	0.4751 (7)	0.6573 (14)	0.021 (3)*
H1W1	0.102 (3)	0.6006 (9)	0.2736 (17)	0.043 (4)*
H2W1	0.206 (3)	0.6521 (8)	0.2292 (17)	0.038 (4)*
H1W2	0.425 (2)	0.6675 (7)	0.0549 (15)	0.030 (4)*
H2W2	0.309 (3)	0.7161 (10)	0.0608 (19)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0222 (3)	0.0097 (2)	0.0151 (2)	−0.0004 (2)	0.0018 (2)	−0.00091 (18)
O2	0.0237 (3)	0.0122 (2)	0.0108 (2)	0.0021 (2)	−0.0033 (2)	−0.00140 (18)
O3	0.0247 (3)	0.0080 (2)	0.0154 (2)	0.0006 (2)	−0.0029 (2)	−0.00218 (18)
O4	0.0206 (3)	0.0099 (2)	0.0112 (2)	0.00154 (19)	−0.0010 (2)	0.00164 (17)
N1	0.0185 (3)	0.0132 (3)	0.0162 (3)	0.0008 (2)	0.0005 (2)	0.0031 (2)
N2	0.0154 (3)	0.0084 (2)	0.0115 (2)	0.0012 (2)	0.0002 (2)	0.00147 (19)
N3	0.0139 (3)	0.0104 (2)	0.0126 (3)	0.0018 (2)	0.0014 (2)	0.00298 (19)
C1	0.0188 (4)	0.0110 (3)	0.0133 (3)	0.0015 (2)	0.0017 (3)	0.0002 (2)
C2	0.0195 (4)	0.0109 (3)	0.0169 (3)	0.0021 (3)	0.0018 (3)	0.0012 (2)
C3	0.0218 (4)	0.0148 (3)	0.0129 (3)	0.0008 (3)	−0.0006 (3)	0.0023 (2)
C4	0.0179 (4)	0.0121 (3)	0.0125 (3)	0.0008 (2)	0.0003 (2)	0.0006 (2)
C5	0.0121 (3)	0.0097 (3)	0.0121 (3)	0.0005 (2)	0.0017 (2)	0.0012 (2)
C6	0.0127 (3)	0.0103 (3)	0.0115 (3)	0.0006 (2)	0.0021 (2)	0.0009 (2)
C7	0.0146 (3)	0.0095 (3)	0.0126 (3)	0.0010 (2)	0.0026 (2)	0.0011 (2)
C8	0.0128 (3)	0.0088 (3)	0.0110 (3)	0.0007 (2)	0.0018 (2)	0.0008 (2)
C9	0.0129 (3)	0.0097 (3)	0.0101 (3)	0.0001 (2)	0.0004 (2)	−0.0001 (2)
C10	0.0137 (3)	0.0084 (3)	0.0116 (3)	−0.0001 (2)	0.0010 (2)	0.0001 (2)
C11	0.0129 (3)	0.0093 (3)	0.0106 (3)	0.0002 (2)	0.0015 (2)	0.0010 (2)
C12	0.0163 (3)	0.0102 (3)	0.0110 (3)	0.0005 (2)	0.0011 (2)	−0.0003 (2)
C13	0.0165 (3)	0.0093 (3)	0.0117 (3)	0.0006 (2)	0.0015 (2)	−0.0004 (2)
O1W	0.0385 (4)	0.0160 (3)	0.0140 (3)	−0.0034 (3)	0.0071 (3)	−0.0002 (2)
O2W	0.0281 (4)	0.0104 (2)	0.0201 (3)	−0.0019 (2)	0.0065 (2)	−0.0011 (2)

Geometric parameters (Å, º) top

O1—C6	1.2326 (9)	C3—H3A	0.988 (13)
O2—C9	1.3743 (9)	C4—C5	1.3941 (10)
O2—H1O2	0.883 (18)	C4—H4A	0.921 (14)
O3—C10	1.3557 (9)	C5—C6	1.5009 (10)
O3—H1O3	0.868 (18)	C7—C8	1.4442 (10)
O4—C11	1.3577 (9)	C7—H7A	0.987 (15)
O4—H1O4	0.895 (18)	C8—C13	1.4011 (10)
N1—C2	1.3380 (10)	C8—C9	1.4060 (10)
N1—C3	1.3428 (11)	C9—C10	1.3954 (10)
N2—C6	1.3524 (9)	C10—C11	1.4047 (10)
N2—N3	1.3809 (9)	C11—C12	1.3965 (10)
N2—H1N2	0.890 (16)	C12—C13	1.3827 (10)
N3—C7	1.2921 (10)	C12—H12A	0.946 (13)
C1—C5	1.3929 (10)	C13—H13A	1.000 (13)
C1—C2	1.3945 (11)	O1W—H1W1	0.926 (18)
C1—H1A	0.988 (13)	O1W—H2W1	0.838 (18)
C2—H2A	0.960 (14)	O2W—H1W2	0.834 (16)
C3—C4	1.3847 (11)	O2W—H2W2	0.863 (19)

C9—O2—H1O2	105.5 (11)	N2—C6—C5	116.10 (6)
C10—O3—H1O3	118.3 (12)	N3—C7—C8	121.57 (7)
C11—O4—H1O4	106.7 (12)	N3—C7—H7A	119.2 (8)
C2—N1—C3	117.41 (7)	C8—C7—H7A	119.2 (8)
C6—N2—N3	118.17 (6)	C13—C8—C9	118.86 (6)
C6—N2—H1N2	124.5 (10)	C13—C8—C7	118.20 (6)
N3—N2—H1N2	117.1 (10)	C9—C8—C7	122.94 (6)
C7—N3—N2	115.84 (6)	O2—C9—C10	117.13 (6)
C5—C1—C2	118.73 (7)	O2—C9—C8	121.91 (6)
C5—C1—H1A	122.3 (8)	C10—C9—C8	120.96 (6)
C2—C1—H1A	118.9 (8)	O3—C10—C9	123.14 (6)
N1—C2—C1	123.29 (7)	O3—C10—C11	118.03 (6)
N1—C2—H2A	117.8 (8)	C9—C10—C11	118.83 (6)
C1—C2—H2A	118.9 (8)	O4—C11—C12	122.13 (6)
N1—C3—C4	123.43 (7)	O4—C11—C10	117.24 (6)
N1—C3—H3A	117.0 (8)	C12—C11—C10	120.63 (6)
C4—C3—H3A	119.6 (8)	C13—C12—C11	119.85 (7)
C3—C4—C5	118.92 (7)	C13—C12—H12A	121.6 (8)
C3—C4—H4A	119.9 (9)	C11—C12—H12A	118.6 (8)
C5—C4—H4A	121.1 (9)	C12—C13—C8	120.85 (7)
C1—C5—C4	118.18 (7)	C12—C13—H13A	122.3 (8)
C1—C5—C6	125.05 (7)	C8—C13—H13A	116.8 (8)
C4—C5—C6	116.76 (6)	H1W1—O1W—H2W1	105.0 (15)
O1—C6—N2	122.73 (7)	H1W2—O2W—H2W2	97.2 (15)
O1—C6—C5	121.16 (7)

C6—N2—N3—C7	179.26 (7)	C13—C8—C9—O2	178.05 (7)
C3—N1—C2—C1	1.77 (14)	C7—C8—C9—O2	−1.23 (12)
C5—C1—C2—N1	−0.22 (14)	C13—C8—C9—C10	−1.49 (12)
C2—N1—C3—C4	−1.57 (14)	C7—C8—C9—C10	179.23 (7)
N1—C3—C4—C5	−0.19 (14)	O2—C9—C10—O3	1.24 (12)
C2—C1—C5—C4	−1.57 (12)	C8—C9—C10—O3	−179.21 (8)
C2—C1—C5—C6	177.13 (8)	O2—C9—C10—C11	−178.29 (7)
C3—C4—C5—C1	1.76 (12)	C8—C9—C10—C11	1.26 (12)
C3—C4—C5—C6	−177.05 (8)	O3—C10—C11—O4	0.08 (11)
N3—N2—C6—O1	−3.53 (12)	C9—C10—C11—O4	179.64 (7)
N3—N2—C6—C5	177.10 (7)	O3—C10—C11—C12	−179.47 (8)
C1—C5—C6—O1	−166.63 (8)	C9—C10—C11—C12	0.09 (12)
C4—C5—C6—O1	12.09 (12)	O4—C11—C12—C13	179.27 (7)
C1—C5—C6—N2	12.74 (12)	C10—C11—C12—C13	−1.20 (12)
C4—C5—C6—N2	−168.54 (7)	C11—C12—C13—C8	0.97 (12)
N2—N3—C7—C8	178.85 (7)	C9—C8—C13—C12	0.35 (12)
N3—C7—C8—C13	177.91 (8)	C7—C8—C13—C12	179.67 (7)
N3—C7—C8—C9	−2.81 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N3	0.883 (18)	1.854 (18)	2.6561 (9)	150.1 (16)
O3—H1O3···N1ⁱ	0.869 (19)	1.835 (19)	2.6911 (10)	168.4 (18)
O4—H1O4···O1W	0.895 (18)	1.769 (18)	2.6559 (9)	170.5 (18)
N2—H1N2···O2Wⁱⁱ	0.890 (16)	2.132 (15)	2.9910 (9)	162.1 (14)
O1W—H1W1···O1ⁱⁱⁱ	0.926 (18)	1.880 (18)	2.7834 (9)	164.6 (16)
O1W—H2W1···O2W	0.837 (19)	2.077 (18)	2.8980 (11)	167.0 (18)
O2W—H1W2···O2^iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2···O4^v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A···O1^vi	0.922 (14)	2.575 (14)	3.2930 (11)	135.1 (11)
C7—H7A···O2Wⁱⁱ	0.988 (14)	2.347 (14)	3.2176 (10)	146.7 (12)

Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1; (iv) x, y, z−1; (v) x, −y+3/2, z−1/2; (vi) −x+2, −y+1, −z+3.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₄·2H₂O
M_r	309.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.9504 (5), 19.9077 (13), 10.0930 (7)
β (°)	106.416 (2)
V (Å³)	1339.60 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.35 × 0.18 × 0.09

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.959, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	21520, 5656, 4668
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.798

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.113, 1.03
No. of reflections	5656
No. of parameters	259
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.26

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
O2—H1O2···N3	0.883 (18)	1.854 (18)	2.6561 (9)	150.1 (16)
O3—H1O3···N1ⁱ	0.869 (19)	1.835 (19)	2.6911 (10)	168.4 (18)
O4—H1O4···O1W	0.895 (18)	1.769 (18)	2.6559 (9)	170.5 (18)
N2—H1N2···O2Wⁱⁱ	0.890 (16)	2.132 (15)	2.9910 (9)	162.1 (14)
O1W—H1W1···O1ⁱⁱⁱ	0.926 (18)	1.880 (18)	2.7834 (9)	164.6 (16)
O1W—H2W1···O2W	0.837 (19)	2.077 (18)	2.8980 (11)	167.0 (18)
O2W—H1W2···O2^iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2···O4^v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A···O1^vi	0.922 (14)	2.575 (14)	3.2930 (11)	135.1 (11)
C7—H7A···O2Wⁱⁱ	0.988 (14)	2.347 (14)	3.2176 (10)	146.7 (12)

Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1; (iv) x, y, z−1; (v) x, −y+3/2, z−1/2; (vi) −x+2, −y+1, −z+3.

Footnotes

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

§Thomson Reuters ResearcherID: C-7576-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under a University Research Grant (No. 1001/PFARMASI/815005). JHG and HKF thank USM for a Research University Grant (No. 1001/PFIZIK/811160). HSNK is grateful to USM for a USM Fellowship.

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