(E)-N′-(2,4,5-Trimethoxy­benzyl­idene)isonicotinohydrazide dihydrate

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810015254

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1235-o1236

https://doi.org/10.1107/S1600536810015254

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(E)-N′-(2,4,5-Trimethoxybenzylidene)isonicotinohydrazide dihydrate

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Chin Sing Yeap ^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 8 April 2010; accepted 26 April 2010; online 30 April 2010)

The asymmetric unit of the title compound, C₁₆H₁₇N₃O₄·2H₂O, contains one Schiff base molecule and two water molecules. The Schiff base molecule exists in an E configuration with respect to the C=N double bond and is essentially planar, the dihedral angle between the benzene and pyridine rings being 5.48 (8)°. The three methoxy groups are also coplanar with the benzene ring [C—O—C—C torsion angles = 3.9 (2), 178.51 (15) and 0.8 (2) Å]. In the crystal structure, the water molecules link the molecules into a three-dimensional network via intermolecular N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For applications of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden & Barry (2000 ); Kahwa et al. (1986 ). For the preparation of the title compound, see: Lourenco et al. (2008 ). For related structures, see: Naveenkumar et al. (2009 , 2010a ,b ); Shi (2005 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₄·2H₂O
M_r = 351.36
Monoclinic, P 2₁
a = 6.8156 (4) Å
b = 14.5648 (10) Å
c = 8.5589 (5) Å
β = 103.421 (2)°
V = 826.42 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.50 × 0.28 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.947, T_max = 0.979
10676 measured reflections
2254 independent reflections
2171 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.126
S = 1.17
2254 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2⋯O1W	0.84	1.93	2.748 (2)	167
O2W—H2W2⋯N1ⁱ	0.83	2.10	2.887 (2)	158
O1W—H1W1⋯O3ⁱⁱ	0.85	2.18	2.8913 (19)	141
O1W—H1W1⋯O4ⁱⁱ	0.85	2.43	3.204 (2)	152
O1W—H2W1⋯O1ⁱⁱⁱ	0.86	1.99	2.834 (2)	170
C4—H4A⋯O2W	0.93	2.34	3.253 (3)	169
C7—H7A⋯O2W	0.93	2.58	3.375 (2)	143
C14—H14A⋯O4ⁱⁱⁱ	0.96	2.60	3.281 (2)	128
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (iii) x, y, z-1.

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/S1600536810015254/kj2145sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015254/kj2145Isup2.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). As a part of a current work of synthesis of such derivatives, in this paper we present the crystal structure of the title compound which was synthesized in our lab.

The asymmetric unit consists of one Schiff base molecule and two water molecules (Fig. 1). The geometry parameters are comparable to those related structures (Naveenkumar et al., 2009, 2010a, b; Shi, 2005). The molecule exists in an E configuration with respect to the C7═N3 double bond. The molecule is essentially coplanar with dihedral angle between the benzene ring and the pyridine ring being 5.48 (8)°. The three methoxy groups are coplanar with the benzene ring [torsion angle, C14–O2–C9–C10 = 3.9 (2), C15–O3–C11–C12 = 178.51 (15), C16–O4–C12–C13 = 0.8 (2) Å]. In the crystal structure, the water molecules link the molecules into a three-dimensional network by the intermolecular N–H···O, O–H···O O–H···N and C–H···O hydrogen bonds (Fig. 2, Table 1).

Related literature top

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For the preparation of the title compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b); Shi (2005). 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). The title compound was prepared by reaction between 2, 4, 5-trimethoxybenzaldehyde (1.0 eq) and isoniazid (1.0 eq) in ethanol/water. After stirring for 1-3 hours 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 yellow single crystal suitable for X-ray analysis was obtained by recrystalization with methanol.

Structure description top

For applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000); Kahwa et al. (1986). For the preparation of the title compound, see: Lourenco et al. (2008). For related structures, see: Naveenkumar et al. (2009, 2010a,b); Shi (2005). 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 with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing the molecules linked into a 3-D network. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(2,4,5-Trimethoxybenzylidene)isonicotinohydrazide dihydrate top

Crystal data top

C₁₆H₁₇N₃O₄·2H₂O	F(000) = 372
M_r = 351.36	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6099 reflections
a = 6.8156 (4) Å	θ = 3.1–37.4°
b = 14.5648 (10) Å	µ = 0.11 mm⁻¹
c = 8.5589 (5) Å	T = 100 K
β = 103.421 (2)°	Block, yellow
V = 826.42 (9) Å³	0.50 × 0.28 × 0.19 mm
Z = 2

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	2171 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 29.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.947, T_max = 0.979	k = −19→19
10676 measured reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.098P)²] where P = (F_o² + 2F_c²)/3
2254 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.57 e Å⁻³
1 restraint	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₆H₁₇N₃O₄·2H₂O	V = 826.42 (9) Å³
M_r = 351.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.8156 (4) Å	µ = 0.11 mm⁻¹
b = 14.5648 (10) Å	T = 100 K
c = 8.5589 (5) Å	0.50 × 0.28 × 0.19 mm
β = 103.421 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	2254 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2171 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.979	R_int = 0.025
10676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.57 e Å⁻³
2254 reflections	Δρ_min = −0.56 e Å⁻³
233 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	0.7986 (2)	0.81175 (12)	1.11648 (15)	0.0180 (3)
O2	0.6823 (2)	1.23398 (11)	0.79017 (15)	0.0156 (3)
O3	0.8195 (2)	1.38828 (11)	1.30523 (16)	0.0189 (3)
O4	0.89952 (19)	1.23697 (11)	1.45332 (14)	0.0162 (3)
N1	0.6308 (2)	0.59240 (13)	0.6538 (2)	0.0172 (3)
N2	0.7323 (2)	0.91163 (13)	0.90629 (17)	0.0130 (3)
N3	0.7635 (2)	0.98623 (13)	1.00977 (19)	0.0138 (3)
C1	0.7218 (3)	0.65940 (15)	0.9179 (2)	0.0171 (4)
H1A	0.7568	0.6505	1.0285	0.020*
C2	0.6821 (3)	0.58454 (16)	0.8141 (2)	0.0206 (4)
H2A	0.6917	0.5260	0.8584	0.025*
C3	0.6190 (3)	0.67728 (16)	0.5943 (2)	0.0170 (4)
H3A	0.5837	0.6841	0.4833	0.020*
C4	0.6562 (3)	0.75638 (15)	0.6879 (2)	0.0165 (4)
H4A	0.6463	0.8141	0.6403	0.020*
C5	0.7087 (2)	0.74703 (14)	0.8545 (2)	0.0118 (4)
C6	0.7510 (2)	0.82624 (14)	0.9712 (2)	0.0126 (4)
C7	0.7415 (2)	1.06540 (15)	0.9400 (2)	0.0127 (3)
H7A	0.7100	1.0685	0.8285	0.015*
C8	0.7652 (2)	1.14993 (14)	1.0336 (2)	0.0117 (3)
C9	0.7321 (2)	1.23481 (15)	0.9547 (2)	0.0122 (4)
C10	0.7488 (3)	1.31661 (14)	1.0429 (2)	0.0131 (4)
H10A	0.7242	1.3727	0.9902	0.016*
C11	0.8021 (2)	1.31332 (14)	1.2090 (2)	0.0130 (4)
C12	0.8412 (2)	1.22870 (15)	1.2901 (2)	0.0128 (4)
C13	0.8203 (2)	1.14806 (14)	1.2032 (2)	0.0116 (3)
H13A	0.8428	1.0921	1.2566	0.014*
C14	0.6607 (3)	1.32161 (15)	0.7124 (2)	0.0168 (4)
H14A	0.6469	1.3133	0.5991	0.025*
H14B	0.7777	1.3584	0.7552	0.025*
H14C	0.5430	1.3519	0.7308	0.025*
C15	0.7866 (3)	1.47619 (16)	1.2305 (2)	0.0184 (4)
H15A	0.7906	1.5225	1.3110	0.028*
H15B	0.6571	1.4771	1.1563	0.028*
H15C	0.8900	1.4882	1.1738	0.028*
C16	0.9457 (3)	1.15432 (15)	1.5425 (2)	0.0176 (4)
H16A	1.0034	1.1687	1.6531	0.026*
H16B	1.0403	1.1191	1.4999	0.026*
H16C	0.8244	1.1193	1.5348	0.026*
H1N2	0.692 (4)	0.923 (2)	0.803 (3)	0.017 (6)*
O2W	0.6218 (2)	0.96947 (12)	0.57107 (16)	0.0189 (3)
H1W2	0.7145	0.9636	0.5228	0.028*
H2W2	0.5246	0.9958	0.5113	0.028*
O1W	0.8961 (2)	0.92446 (13)	0.39361 (16)	0.0228 (3)
H1W1	0.9693	0.8884	0.4600	0.034*
H2W1	0.8554	0.8950	0.3055	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0273 (7)	0.0138 (8)	0.0110 (6)	0.0009 (5)	0.0009 (5)	0.0001 (5)
O2	0.0256 (6)	0.0115 (7)	0.0088 (6)	−0.0002 (5)	0.0017 (4)	0.0008 (5)
O3	0.0313 (7)	0.0101 (7)	0.0128 (6)	0.0004 (6)	0.0003 (5)	−0.0028 (5)
O4	0.0261 (6)	0.0122 (7)	0.0085 (5)	0.0014 (5)	0.0004 (4)	0.0006 (5)
N1	0.0194 (6)	0.0137 (9)	0.0176 (8)	−0.0008 (6)	0.0025 (5)	−0.0044 (6)
N2	0.0178 (6)	0.0097 (8)	0.0105 (6)	−0.0013 (6)	0.0016 (5)	−0.0023 (6)
N3	0.0161 (6)	0.0103 (8)	0.0143 (6)	−0.0011 (6)	0.0020 (5)	−0.0030 (6)
C1	0.0249 (8)	0.0123 (10)	0.0136 (8)	−0.0001 (7)	0.0035 (6)	0.0005 (7)
C2	0.0328 (9)	0.0099 (10)	0.0185 (9)	−0.0008 (8)	0.0045 (7)	−0.0008 (8)
C3	0.0202 (7)	0.0144 (10)	0.0148 (8)	0.0010 (7)	0.0010 (6)	−0.0023 (7)
C4	0.0214 (8)	0.0126 (10)	0.0139 (8)	0.0016 (7)	0.0008 (6)	0.0002 (7)
C5	0.0122 (6)	0.0100 (10)	0.0128 (7)	−0.0002 (6)	0.0025 (5)	−0.0016 (7)
C6	0.0132 (7)	0.0126 (10)	0.0115 (7)	−0.0002 (6)	0.0018 (5)	−0.0008 (6)
C7	0.0137 (6)	0.0121 (9)	0.0119 (7)	−0.0008 (6)	0.0024 (5)	−0.0031 (7)
C8	0.0138 (7)	0.0094 (9)	0.0118 (8)	−0.0003 (6)	0.0025 (5)	−0.0013 (6)
C9	0.0136 (7)	0.0125 (9)	0.0100 (7)	−0.0007 (7)	0.0017 (5)	−0.0017 (7)
C10	0.0169 (7)	0.0090 (9)	0.0129 (7)	−0.0001 (7)	0.0024 (6)	−0.0007 (7)
C11	0.0153 (7)	0.0098 (10)	0.0133 (8)	−0.0003 (7)	0.0020 (6)	−0.0026 (7)
C12	0.0145 (6)	0.0136 (10)	0.0095 (7)	0.0005 (7)	0.0010 (5)	−0.0003 (7)
C13	0.0126 (6)	0.0098 (9)	0.0121 (7)	−0.0006 (6)	0.0020 (5)	0.0006 (6)
C14	0.0252 (8)	0.0124 (10)	0.0123 (7)	0.0002 (7)	0.0034 (6)	0.0018 (7)
C15	0.0255 (8)	0.0096 (9)	0.0185 (8)	0.0006 (7)	0.0016 (6)	−0.0027 (7)
C16	0.0244 (8)	0.0154 (10)	0.0129 (7)	0.0018 (7)	0.0042 (6)	0.0042 (7)
O2W	0.0265 (6)	0.0172 (8)	0.0127 (6)	0.0040 (6)	0.0039 (5)	0.0029 (6)
O1W	0.0282 (7)	0.0261 (9)	0.0118 (6)	0.0080 (6)	0.0002 (5)	−0.0026 (6)

Geometric parameters (Å, º) top

O1—C6	1.228 (2)	C7—H7A	0.9300
O2—C9	1.3700 (19)	C8—C9	1.402 (3)
O2—C14	1.431 (2)	C8—C13	1.412 (2)
O3—C11	1.356 (2)	C9—C10	1.401 (3)
O3—C15	1.426 (3)	C10—C11	1.384 (2)
O4—C12	1.366 (2)	C10—H10A	0.9300
O4—C16	1.421 (2)	C11—C12	1.410 (3)
N1—C3	1.332 (3)	C12—C13	1.380 (3)
N1—C2	1.340 (3)	C13—H13A	0.9300
N2—C6	1.356 (3)	C14—H14A	0.9600
N2—N3	1.387 (2)	C14—H14B	0.9600
N2—H1N2	0.88 (3)	C14—H14C	0.9600
N3—C7	1.291 (3)	C15—H15A	0.9600
C1—C5	1.381 (3)	C15—H15B	0.9600
C1—C2	1.393 (3)	C15—H15C	0.9600
C1—H1A	0.9300	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.392 (3)	C16—H16C	0.9600
C3—H3A	0.9300	O2W—H1W2	0.8358
C4—C5	1.394 (2)	O2W—H2W2	0.8306
C4—H4A	0.9300	O1W—H1W1	0.8468
C5—C6	1.509 (3)	O1W—H2W1	0.8562
C7—C8	1.457 (3)

C9—O2—C14	116.38 (15)	C10—C9—C8	120.44 (15)
C11—O3—C15	117.89 (14)	C11—C10—C9	119.55 (17)
C12—O4—C16	116.76 (16)	C11—C10—H10A	120.2
C3—N1—C2	116.66 (17)	C9—C10—H10A	120.2
C6—N2—N3	118.09 (14)	O3—C11—C10	124.14 (17)
C6—N2—H1N2	124 (2)	O3—C11—C12	115.12 (15)
N3—N2—H1N2	117 (2)	C10—C11—C12	120.74 (17)
C7—N3—N2	114.86 (15)	O4—C12—C13	126.55 (18)
C5—C1—C2	119.19 (17)	O4—C12—C11	113.82 (17)
C5—C1—H1A	120.4	C13—C12—C11	119.64 (15)
C2—C1—H1A	120.4	C12—C13—C8	120.47 (17)
N1—C2—C1	123.5 (2)	C12—C13—H13A	119.8
N1—C2—H2A	118.2	C8—C13—H13A	119.8
C1—C2—H2A	118.2	O2—C14—H14A	109.5
N1—C3—C4	124.15 (17)	O2—C14—H14B	109.5
N1—C3—H3A	117.9	H14A—C14—H14B	109.5
C4—C3—H3A	117.9	O2—C14—H14C	109.5
C3—C4—C5	118.48 (18)	H14A—C14—H14C	109.5
C3—C4—H4A	120.8	H14B—C14—H14C	109.5
C5—C4—H4A	120.8	O3—C15—H15A	109.5
C1—C5—C4	118.01 (17)	O3—C15—H15B	109.5
C1—C5—C6	117.48 (15)	H15A—C15—H15B	109.5
C4—C5—C6	124.52 (18)	O3—C15—H15C	109.5
O1—C6—N2	123.39 (17)	H15A—C15—H15C	109.5
O1—C6—C5	120.23 (18)	H15B—C15—H15C	109.5
N2—C6—C5	116.38 (15)	O4—C16—H16A	109.5
N3—C7—C8	120.95 (15)	O4—C16—H16B	109.5
N3—C7—H7A	119.5	H16A—C16—H16B	109.5
C8—C7—H7A	119.5	O4—C16—H16C	109.5
C9—C8—C13	119.13 (16)	H16A—C16—H16C	109.5
C9—C8—C7	119.69 (15)	H16B—C16—H16C	109.5
C13—C8—C7	121.18 (17)	H1W2—O2W—H2W2	109.2
O2—C9—C10	122.09 (17)	H1W1—O1W—H2W1	107.4
O2—C9—C8	117.47 (16)

C6—N2—N3—C7	−179.38 (14)	C13—C8—C9—O2	178.90 (14)
C3—N1—C2—C1	0.2 (3)	C7—C8—C9—O2	−1.3 (2)
C5—C1—C2—N1	−0.1 (3)	C13—C8—C9—C10	−1.5 (2)
C2—N1—C3—C4	−0.1 (3)	C7—C8—C9—C10	178.21 (15)
N1—C3—C4—C5	−0.2 (3)	O2—C9—C10—C11	−179.21 (14)
C2—C1—C5—C4	−0.1 (3)	C8—C9—C10—C11	1.3 (2)
C2—C1—C5—C6	179.42 (16)	C15—O3—C11—C10	−1.9 (2)
C3—C4—C5—C1	0.3 (3)	C15—O3—C11—C12	178.51 (15)
C3—C4—C5—C6	−179.27 (16)	C9—C10—C11—O3	−179.05 (15)
N3—N2—C6—O1	−1.7 (2)	C9—C10—C11—C12	0.5 (2)
N3—N2—C6—C5	177.93 (14)	C16—O4—C12—C13	0.8 (2)
C1—C5—C6—O1	1.3 (2)	C16—O4—C12—C11	−178.67 (14)
C4—C5—C6—O1	−179.19 (16)	O3—C11—C12—O4	−2.9 (2)
C1—C5—C6—N2	−178.42 (15)	C10—C11—C12—O4	177.57 (14)
C4—C5—C6—N2	1.1 (2)	O3—C11—C12—C13	177.65 (15)
N2—N3—C7—C8	178.65 (14)	C10—C11—C12—C13	−1.9 (2)
N3—C7—C8—C9	−177.35 (15)	O4—C12—C13—C8	−177.80 (15)
N3—C7—C8—C13	2.4 (2)	C11—C12—C13—C8	1.6 (2)
C14—O2—C9—C10	3.9 (2)	C9—C8—C13—C12	0.1 (2)
C14—O2—C9—C8	−176.53 (14)	C7—C8—C13—C12	−179.66 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2···O1W	0.84	1.93	2.748 (2)	167
O2W—H2W2···N1ⁱ	0.83	2.10	2.887 (2)	158
O1W—H1W1···O3ⁱⁱ	0.85	2.18	2.8913 (19)	141
O1W—H1W1···O4ⁱⁱ	0.85	2.43	3.204 (2)	152
O1W—H2W1···O1ⁱⁱⁱ	0.86	1.99	2.834 (2)	170
C4—H4A···O2W	0.93	2.34	3.253 (3)	169
C7—H7A···O2W	0.93	2.58	3.375 (2)	143
C14—H14A···O4ⁱⁱⁱ	0.96	2.60	3.281 (2)	128

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₄·2H₂O
M_r	351.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	6.8156 (4), 14.5648 (10), 8.5589 (5)
β (°)	103.421 (2)
V (Å³)	826.42 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.28 × 0.19

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.947, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10676, 2254, 2171
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.126, 1.17
No. of reflections	2254
No. of parameters	233
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.56

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
N2—H1N2···O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2···O1W	0.8400	1.9300	2.748 (2)	167.00
O2W—H2W2···N1ⁱ	0.8300	2.1000	2.887 (2)	158.00
O1W—H1W1···O3ⁱⁱ	0.8500	2.1800	2.8913 (19)	141.00
O1W—H1W1···O4ⁱⁱ	0.8500	2.4300	3.204 (2)	152.00
O1W—H2W1···O1ⁱⁱⁱ	0.8600	1.9900	2.834 (2)	170.00
C4—H4A···O2W	0.9300	2.3400	3.253 (3)	169.00
C7—H7A···O2W	0.9300	2.5800	3.375 (2)	143.00
C14—H14A···O4ⁱⁱⁱ	0.9600	2.6000	3.281 (2)	128.00

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

Footnotes

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

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the Fundamental Research Grant Scheme (203/PFARMASI/671157). HSNK and CSY are grateful to USM for USM fellowships. HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012).

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