(E)-N'-(2-Hydr-oxy-4-methoxy-benzyl-idene)isonicotinohydrazide monohydrate.

The title compound, C(14)H(13)N(3)O(3)·H(2)O, was prepared by the reaction of 4-methoxy-salicylaldehyde and isonicotinohydrazide in ethanol. The Schiff base mol-ecule is not planar and has an E configuration with respect to the methyl-idene unit. The dihedral angle between the benzene and pyridine rings is 36.8 (2)°. In the mol-ecule there is an intra-molecular O-H⋯N hydrogen bond involving the hydroxyl substituent and the N atom of the 2-hydr-oxy-4-methoxy-benzyl-idene unit. In the crystal, the mol-ecules are linked through inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008 ▶); Chen et al. (2008 ▶); Alvarez et al. (2008 ▶); Ventura & Martins (2008 ▶); Kalinowski et al. (2008 ▶). For related structures, see: Peng & Hou (2008 ▶); Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yehye et al. (2008 ▶); Ejsmont et al. (2008 ▶); Han et al. (2006 ▶); Lu et al. (2008 ▶).

Experimental

Crystal data

C14H13N3O3·H2O

M = 289.29

Monoclinic,

a = 7.299 (4) Å

b = 12.537 (6) Å

c = 14.808 (7) Å

β = 96.281 (8)°

V = 1346.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.976, T max = 0.977

7804 measured reflections

3041 independent reflections

2129 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.03

3041 reflections

201 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029619/su2062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029619/su2062Isup2.hkl

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

C14H13N3O3·H2O	F(000) = 608
Mr = 289.29	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1237 reflections
a = 7.299 (4) Å	θ = 2.4–24.5°
b = 12.537 (6) Å	µ = 0.11 mm−1
c = 14.808 (7) Å	T = 298 K
β = 96.281 (8)°	Block, colorless
V = 1346.9 (11) Å3	0.23 × 0.23 × 0.22 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	2129 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.976, Tmax = 0.977	k = −16→15
7804 measured reflections	l = −14→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.2867P] where P = (Fo2 + 2Fc2)/3
3041 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.18 e Å−3
4 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
O1	0.1869 (2)	0.17985 (9)	1.00835 (8)	0.0519 (4)
H1	0.2127	0.1524	0.9611	0.078*
O2	0.3338 (2)	0.13791 (9)	0.75220 (8)	0.0490 (4)
O3	0.07206 (17)	0.08252 (9)	1.30718 (7)	0.0407 (3)
O4	0.3910 (2)	0.75061 (10)	0.34205 (9)	0.0532 (4)
N1	0.29393 (19)	0.02521 (11)	0.90464 (9)	0.0348 (3)
N2	0.3324 (2)	−0.02124 (11)	0.82441 (9)	0.0339 (3)
N3	0.3613 (2)	−0.13153 (13)	0.50292 (10)	0.0496 (4)
C1	0.2257 (2)	−0.00223 (12)	1.05635 (10)	0.0307 (4)
C2	0.1816 (2)	0.10410 (13)	1.07253 (10)	0.0324 (4)
C3	0.1288 (2)	0.13524 (13)	1.15565 (10)	0.0342 (4)
H3	0.0991	0.2061	1.1657	0.041*
C4	0.1205 (2)	0.06050 (13)	1.22317 (10)	0.0312 (4)
C5	0.1644 (2)	−0.04517 (13)	1.20894 (11)	0.0370 (4)
H5	0.1592	−0.0953	1.2549	0.044*
C6	0.2154 (2)	−0.07474 (13)	1.12659 (11)	0.0382 (4)
H6	0.2442	−0.1458	1.1172	0.046*
C7	0.2761 (2)	−0.03892 (14)	0.97002 (11)	0.0355 (4)
H7	0.2962	−0.1114	0.9618	0.043*
C8	0.3435 (2)	0.04041 (13)	0.75139 (10)	0.0335 (4)
C9	0.3600 (2)	−0.01964 (12)	0.66533 (10)	0.0317 (4)
C10	0.2673 (3)	0.01868 (15)	0.58540 (11)	0.0417 (4)
H10	0.2037	0.0830	0.5847	0.050*
C11	0.2709 (3)	−0.03991 (16)	0.50692 (12)	0.0501 (5)
H11	0.2064	−0.0139	0.4538	0.060*
C12	0.4556 (3)	−0.16551 (15)	0.57962 (12)	0.0442 (5)
H12	0.5238	−0.2280	0.5776	0.053*
C13	0.4581 (2)	−0.11375 (13)	0.66161 (11)	0.0358 (4)
H13	0.5244	−0.1414	0.7136	0.043*
C14	0.0200 (3)	0.18921 (14)	1.32548 (12)	0.0460 (5)
H14A	0.1199	0.2366	1.3168	0.069*
H14B	−0.0087	0.1943	1.3871	0.069*
H14C	−0.0864	0.2086	1.2849	0.069*
H2	0.342 (3)	−0.0930 (8)	0.8225 (16)	0.080*
H4A	0.380 (3)	0.7860 (16)	0.3910 (10)	0.080*
H4B	0.476 (2)	0.7815 (17)	0.3165 (13)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0907 (11)	0.0363 (7)	0.0306 (7)	−0.0014 (7)	0.0150 (7)	0.0072 (5)
O2	0.0739 (10)	0.0350 (7)	0.0413 (7)	0.0045 (6)	0.0206 (6)	0.0002 (5)
O3	0.0562 (8)	0.0416 (7)	0.0263 (6)	0.0017 (6)	0.0139 (5)	−0.0029 (5)
O4	0.0814 (11)	0.0405 (8)	0.0406 (8)	−0.0106 (7)	0.0193 (7)	−0.0080 (6)
N1	0.0376 (8)	0.0437 (8)	0.0241 (7)	−0.0035 (6)	0.0080 (6)	−0.0041 (6)
N2	0.0423 (8)	0.0373 (8)	0.0234 (7)	−0.0013 (6)	0.0093 (6)	−0.0038 (6)
N3	0.0564 (11)	0.0604 (11)	0.0340 (9)	−0.0128 (8)	0.0148 (7)	−0.0113 (7)
C1	0.0321 (9)	0.0351 (9)	0.0252 (8)	−0.0028 (7)	0.0045 (6)	−0.0011 (7)
C2	0.0401 (10)	0.0319 (8)	0.0248 (8)	−0.0056 (7)	0.0022 (7)	0.0034 (6)
C3	0.0454 (10)	0.0276 (8)	0.0297 (9)	−0.0012 (7)	0.0050 (7)	−0.0028 (7)
C4	0.0326 (9)	0.0382 (9)	0.0231 (8)	−0.0031 (7)	0.0048 (6)	−0.0021 (7)
C5	0.0497 (11)	0.0346 (9)	0.0279 (9)	0.0011 (8)	0.0095 (7)	0.0067 (7)
C6	0.0505 (11)	0.0308 (9)	0.0345 (9)	0.0045 (8)	0.0105 (8)	0.0007 (7)
C7	0.0401 (10)	0.0380 (9)	0.0289 (9)	−0.0008 (7)	0.0066 (7)	−0.0029 (7)
C8	0.0366 (9)	0.0356 (9)	0.0293 (9)	0.0004 (7)	0.0087 (7)	0.0002 (7)
C9	0.0349 (9)	0.0354 (9)	0.0262 (8)	−0.0042 (7)	0.0094 (6)	0.0010 (7)
C10	0.0488 (11)	0.0458 (10)	0.0313 (9)	0.0046 (8)	0.0081 (8)	0.0052 (8)
C11	0.0562 (13)	0.0653 (13)	0.0286 (10)	−0.0055 (10)	0.0042 (8)	0.0029 (9)
C12	0.0471 (11)	0.0433 (10)	0.0447 (11)	−0.0026 (8)	0.0166 (9)	−0.0090 (8)
C13	0.0364 (10)	0.0408 (9)	0.0312 (9)	−0.0027 (7)	0.0082 (7)	0.0002 (7)
C14	0.0585 (12)	0.0435 (10)	0.0387 (10)	−0.0069 (9)	0.0171 (8)	−0.0122 (8)

O1—C2	1.3471 (19)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.385 (2)
O2—C8	1.224 (2)	C5—C6	1.365 (2)
O3—C4	1.3583 (19)	C5—H5	0.9300
O3—C14	1.425 (2)	C6—H6	0.9300
O4—H4A	0.861 (9)	C7—H7	0.9300
O4—H4B	0.853 (9)	C8—C9	1.496 (2)
N1—C7	1.276 (2)	C9—C10	1.383 (2)
N1—N2	1.3791 (19)	C9—C13	1.384 (2)
N2—C8	1.339 (2)	C10—C11	1.377 (2)
N2—H2	0.903 (9)	C10—H10	0.9300
N3—C11	1.329 (3)	C11—H11	0.9300
N3—C12	1.332 (2)	C12—C13	1.375 (2)
C1—C6	1.390 (2)	C12—H12	0.9300
C1—C2	1.398 (2)	C13—H13	0.9300
C1—C7	1.444 (2)	C14—H14A	0.9600
C2—C3	1.386 (2)	C14—H14B	0.9600
C3—C4	1.376 (2)	C14—H14C	0.9600
C2—O1—H1	109.5	N1—C7—H7	119.1
C4—O3—C14	117.81 (13)	C1—C7—H7	119.1
H4A—O4—H4B	106.4 (17)	O2—C8—N2	124.03 (15)
C7—N1—N2	115.77 (14)	O2—C8—C9	121.38 (14)
C8—N2—N1	119.21 (14)	N2—C8—C9	114.52 (14)
C8—N2—H2	122.6 (15)	C10—C9—C13	117.94 (15)
N1—N2—H2	118.1 (15)	C10—C9—C8	118.47 (15)
C11—N3—C12	116.82 (15)	C13—C9—C8	123.55 (15)
C6—C1—C2	117.59 (14)	C11—C10—C9	118.96 (17)
C6—C1—C7	119.62 (15)	C11—C10—H10	120.5
C2—C1—C7	122.77 (14)	C9—C10—H10	120.5
O1—C2—C3	117.41 (15)	N3—C11—C10	123.61 (17)
O1—C2—C1	121.76 (14)	N3—C11—H11	118.2
C3—C2—C1	120.83 (14)	C10—C11—H11	118.2
C4—C3—C2	119.47 (15)	N3—C12—C13	123.90 (18)
C4—C3—H3	120.3	N3—C12—H12	118.1
C2—C3—H3	120.3	C13—C12—H12	118.1
O3—C4—C3	124.30 (15)	C12—C13—C9	118.71 (16)
O3—C4—C5	114.93 (14)	C12—C13—H13	120.6
C3—C4—C5	120.77 (15)	C9—C13—H13	120.6
C6—C5—C4	119.09 (15)	O3—C14—H14A	109.5
C6—C5—H5	120.5	O3—C14—H14B	109.5
C4—C5—H5	120.5	H14A—C14—H14B	109.5
C5—C6—C1	122.25 (16)	O3—C14—H14C	109.5
C5—C6—H6	118.9	H14A—C14—H14C	109.5
C1—C6—H6	118.9	H14B—C14—H14C	109.5
N1—C7—C1	121.88 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.644 (2)	146.
O4—H4B···O2i	0.85 (1)	2.07 (1)	2.924 (2)	176 (2)
O4—H4A···N3ii	0.86 (1)	1.97 (1)	2.832 (2)	178 (2)
N2—H2···O4iii	0.90 (1)	2.02 (1)	2.915 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.644 (2)	146
O4—H4B⋯O2i	0.853 (9)	2.072 (10)	2.924 (2)	176 (2)
O4—H4A⋯N3ii	0.861 (9)	1.971 (10)	2.832 (2)	178 (2)
N2—H2⋯O4iii	0.903 (9)	2.024 (11)	2.915 (2)	169 (2)

Symmetry codes: (i) ; (ii) ; (iii) .