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organic compounds
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(E)-N′-(2,4,6-Trihydroxybenzylidene)isonicotinohydrazide sesquihydrate
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
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 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 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
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S1600536810014959/is2532sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014959/is2532Isup2.hkl
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.
All the H atoms were located from a difference Fourier map. H1W1, H2W1, H1W2 and H2W2 were allowed to ride on their parent atoms to which they were attached, with Uiso(H) = 1.5Ueq(parent atom). The remaining H were refined freely. [O—H = 0.74 (3)–0.974 (10) Å, N—H = 0.88 (2) Å and C—H = 0.895 (19)–1.025 (18) Å]. The partially-occupied disordered water molecule was fixed at 50% occupancy in the final refinement.
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).
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 of the title compound.The
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 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).
is further stabilized byFor biological applications of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden & Barry (2000). For the biological activity of
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).Data collection: APEX2 (Bruker, 2009); cell
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).C13H11N3O4·1.5H2O | F(000) = 628 |
Mr = 300.27 | Dx = 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 |
Bruker SMART APEXII CCD area-detector diffractometer | 3795 independent reflections |
Radiation source: fine-focus sealed tube | 3090 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 30.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→9 |
Tmin = 0.944, Tmax = 0.977 | k = −16→18 |
14912 measured reflections | l = −18→18 |
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(Fo2) + (0.086P)2 + 0.1988P] where P = (Fo2 + 2Fc2)/3 |
3795 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C13H11N3O4·1.5H2O | V = 1302.30 (3) Å3 |
Mr = 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)° |
Bruker SMART APEXII CCD area-detector diffractometer | 3795 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3090 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.977 | Rint = 0.025 |
14912 measured reflections |
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 | Δρmax = 0.38 e Å−3 |
3795 reflections | Δρmin = −0.38 e Å−3 |
244 parameters |
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. |
x | y | z | Uiso*/Ueq | 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)* |
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) |
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. |
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···N3iv | 0.87 (3) | 1.82 (3) | 2.6470 (14) | 158 (3) |
O3—H1O3···O1v | 0.72 (3) | 2.16 (3) | 2.7579 (15) | 142 (3) |
O3—H1O3···O2Wvi | 0.72 (3) | 2.40 (3) | 2.970 (2) | 138 (3) |
C4—H4A···O2Wvi | 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 |
Mr | 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) |
Tmin, Tmax | 0.944, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14912, 3795, 3090 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.38, −0.38 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
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···N3iv | 0.87 (3) | 1.82 (3) | 2.6470 (14) | 158 (3) |
O3—H1O3···O1v | 0.72 (3) | 2.16 (3) | 2.7579 (15) | 142 (3) |
O3—H1O3···O2Wvi | 0.72 (3) | 2.40 (3) | 2.970 (2) | 138 (3) |
C4—H4A···O2Wvi | 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. |
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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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).