(E)-N'-(2,3,4-Trihy-droxy-benzyl-idene)-isonicotinohydrazide dihydrate.

In the title isoniazid derivative, C(13)H(11)N(3)O(4)·2H(2)O, the Schiff base mol-ecule exists in an E configuration with respect to the acyclic C=N bond. An intra-molecular 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, inter-molecular O-H⋯N, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into two-dimensional arrays lying parallel to the (10) plane. These arrays are further inter-connected into a three-dimensional extended network via O-H⋯O and C-H⋯O hydrogen bonds. A weak inter-molecular π-π inter-action [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 = 309.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.03

5656 reflections

259 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.26 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/S1600536810043965/rz2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043965/rz2508Isup2.hkl

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

C13H11N3O4·2H2O	F(000) = 648
Mr = 309.28	Dx = 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

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

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(Fo2) + (0.0651P)2 + 0.2238P] where P = (Fo2 + 2Fc2)/3
5656 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.26 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 > 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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O2iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2···O4v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A···O1vi	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)

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⋯O2iv	0.831 (15)	2.161 (15)	2.9570 (11)	160.3 (14)
O2W—H2W2⋯O4v	0.86 (2)	1.91 (2)	2.7688 (9)	173.3 (19)
C4—H4A⋯O1vi	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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .