(E)-N'-(2,4,6-Trihydroxy-benzyl-idene)isonicotinohydrazide sesquihydrate.

In the title compound, C(13)H(11)N(3)O(4)·1.5H(2)O, the pyridine ring forms a dihedral angle of 1.50 (6)° with the benzene ring. An intra-molecular O-H⋯N hydrogen bond forms a six-membered ring with an S(6) ring motif. In the crystal structure, one water mol-ecule is disordered over two positions around an inversion centre with site-occupancy factors of 0.5. Inter-molecular 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 inter-action 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 = 300.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.139

S = 1.05

3795 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.38 e Å−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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014959/is2532Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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)

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)

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⋯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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .