N'-[(E)-2-Hy-droxy-5-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide monohydrate.

The title compound, C14H13N3O3·H2O, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, the lattice water molecule plays a major role in the supramolecular architecture by interconnecting adjacent molecules into a three-dimensional netwrok by means of O-H⋯O, O-H⋯N and N-H⋯O hydrogen-bonding inter-actions. The structure also features two non-classical C-H⋯O inter-actions.

Related literature

For properties of carbohydrazide and its derivatives, see: Mangalam & Kurup (2011 ▶). For mol­ecular sensing of metals, see: Bakir & Brown (2002 ▶). For related structures and background references, see: Kargar et al. (2010 ▶); Shafiq et al. (2009 ▶); Sithambaresan & Kurup (2011 ▶). For the synthesis, see: Mangalam et al. (2009 ▶).

Experimental

Crystal data

C14H13N3O3·H2O

M = 289.29

Orthorhombic,

a = 12.6455 (16) Å

b = 12.7423 (16) Å

c = 8.9306 (9) Å

V = 1439.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.965, T max = 0.976

10294 measured reflections

1668 independent reflections

1134 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.00

1668 reflections

208 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301235X/fj2628sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301235X/fj2628Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301235X/fj2628Isup3.cml

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

C14H13N3O3·H2O	F(000) = 608
Mr = 289.29	Dx = 1.335 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1943 reflections
a = 12.6455 (16) Å	θ = 2.8–27.5°
b = 12.7423 (16) Å	µ = 0.10 mm−1
c = 8.9306 (9) Å	T = 296 K
V = 1439.0 (3) Å3	Block, yellow
Z = 4	0.40 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	1668 independent reflections
Radiation source: fine-focus sealed tube	1134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 8.33 pixels mm-1	θmax = 27.0°, θmin = 2.8°
ω and φ scan	h = −16→15
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→16
Tmin = 0.965, Tmax = 0.976	l = −11→9
10294 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0701P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1668 reflections	Δρmax = 0.17 e Å−3
208 parameters	Δρmin = −0.15 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (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	0.1808 (2)	0.4322 (3)	−0.0082 (3)	0.0751 (10)
O2	0.4338 (2)	0.2150 (3)	0.3839 (3)	0.0617 (9)
O3	0.37204 (18)	0.1124 (2)	0.7981 (3)	0.0518 (7)
O1S	1.0079 (2)	0.2238 (2)	0.7337 (4)	0.0590 (8)
N1	0.2710 (2)	0.2049 (2)	0.5685 (3)	0.0397 (7)
N2	0.2196 (2)	0.1700 (3)	0.6956 (3)	0.0408 (7)
N3	0.1091 (3)	−0.0404 (3)	1.1458 (4)	0.0575 (9)
C1	0.3661 (3)	0.2681 (3)	0.2933 (4)	0.0411 (8)
C2	0.4043 (3)	0.3044 (3)	0.1575 (4)	0.0507 (10)
H2	0.4747	0.2928	0.1326	0.061*
C3	0.3409 (3)	0.3566 (3)	0.0601 (4)	0.0533 (11)
H3	0.3679	0.3792	−0.0312	0.064*
C4	0.2361 (3)	0.3764 (3)	0.0963 (4)	0.0497 (10)
C5	0.1962 (3)	0.3413 (3)	0.2291 (4)	0.0428 (9)
H5	0.1257	0.3540	0.2528	0.051*
C6	0.2605 (3)	0.2865 (3)	0.3301 (3)	0.0353 (8)
C7	0.2147 (3)	0.2507 (3)	0.4707 (4)	0.0391 (8)
H7	0.1432	0.2615	0.4890	0.047*
C8	0.2760 (3)	0.1203 (3)	0.8009 (3)	0.0360 (8)
C9	0.2130 (2)	0.0700 (3)	0.9218 (3)	0.0345 (8)
C10	0.2574 (3)	0.0576 (3)	1.0612 (5)	0.0558 (11)
H10	0.3236	0.0856	1.0823	0.067*
C11	0.2026 (4)	0.0036 (4)	1.1683 (5)	0.0651 (13)
H11	0.2329	−0.0025	1.2628	0.078*
C12	0.0673 (3)	−0.0275 (3)	1.0122 (5)	0.0513 (10)
H12	0.0012	−0.0569	0.9941	0.062*
C13	0.1150 (3)	0.0265 (3)	0.8976 (4)	0.0404 (8)
H13	0.0817	0.0336	0.8053	0.049*
C14	0.0712 (4)	0.4431 (4)	0.0117 (5)	0.0759 (15)
H14A	0.0391	0.3750	0.0175	0.114*
H14B	0.0418	0.4810	−0.0714	0.114*
H14C	0.0576	0.4809	0.1027	0.114*
H2'	0.1551 (15)	0.191 (3)	0.720 (5)	0.054 (12)*
H1A	0.973 (3)	0.279 (2)	0.757 (6)	0.093 (19)*
H1B	0.962 (3)	0.175 (2)	0.722 (6)	0.081 (16)*
H2A	0.400 (3)	0.198 (3)	0.462 (3)	0.066 (14)*

	U11	U22	U33	U12	U13	U23
O1	0.069 (2)	0.106 (3)	0.0501 (17)	−0.0069 (18)	−0.0104 (16)	0.0408 (18)
O2	0.0470 (15)	0.080 (2)	0.0580 (18)	0.0194 (14)	0.0147 (16)	0.0220 (16)
O3	0.0316 (13)	0.0695 (19)	0.0542 (15)	−0.0047 (12)	−0.0016 (12)	0.0243 (13)
O1S	0.0376 (14)	0.0544 (18)	0.085 (2)	0.0050 (14)	−0.0006 (15)	−0.0197 (16)
N1	0.0355 (15)	0.0484 (18)	0.0351 (15)	−0.0004 (14)	0.0036 (14)	0.0125 (14)
N2	0.0352 (16)	0.0528 (19)	0.0343 (16)	0.0034 (15)	0.0074 (14)	0.0151 (13)
N3	0.056 (2)	0.063 (2)	0.054 (2)	−0.0059 (18)	0.0109 (17)	0.0184 (17)
C1	0.0422 (19)	0.042 (2)	0.0394 (18)	0.0026 (16)	0.0076 (16)	0.0070 (16)
C2	0.046 (2)	0.060 (3)	0.046 (2)	−0.0011 (19)	0.0176 (18)	0.0028 (18)
C3	0.063 (3)	0.063 (3)	0.0331 (19)	−0.006 (2)	0.0128 (19)	0.0101 (18)
C4	0.055 (3)	0.058 (3)	0.036 (2)	−0.0101 (19)	−0.0029 (19)	0.0129 (19)
C5	0.0341 (18)	0.055 (2)	0.040 (2)	−0.0037 (16)	−0.0040 (16)	0.0079 (18)
C6	0.0357 (18)	0.037 (2)	0.0327 (18)	−0.0067 (14)	0.0004 (15)	0.0028 (15)
C7	0.0307 (18)	0.051 (2)	0.0357 (19)	−0.0024 (16)	0.0034 (15)	0.0033 (16)
C8	0.0342 (18)	0.0392 (19)	0.0346 (18)	−0.0041 (15)	−0.0024 (16)	0.0083 (15)
C9	0.0324 (17)	0.0366 (19)	0.0346 (18)	−0.0009 (14)	0.0022 (15)	0.0044 (15)
C10	0.054 (3)	0.070 (3)	0.044 (2)	−0.022 (2)	−0.011 (2)	0.017 (2)
C11	0.072 (3)	0.086 (4)	0.036 (2)	−0.021 (3)	−0.0063 (19)	0.023 (2)
C12	0.0378 (19)	0.053 (3)	0.063 (3)	−0.0039 (17)	0.0056 (19)	0.014 (2)
C13	0.0373 (18)	0.043 (2)	0.0413 (19)	−0.0026 (15)	−0.0012 (16)	0.0073 (16)
C14	0.066 (3)	0.086 (4)	0.076 (3)	−0.016 (3)	−0.030 (3)	0.036 (3)

O1—C4	1.366 (4)	C3—H3	0.9300
O1—C14	1.405 (5)	C4—C5	1.364 (5)
O2—C1	1.358 (5)	C5—C6	1.402 (5)
O2—H2A	0.847 (10)	C5—H5	0.9300
O3—C8	1.218 (4)	C6—C7	1.456 (5)
O1S—H1A	0.856 (10)	C7—H7	0.9300
O1S—H1B	0.859 (10)	C8—C9	1.487 (4)
N1—C7	1.269 (4)	C9—C13	1.374 (5)
N1—N2	1.381 (4)	C9—C10	1.374 (5)
N2—C8	1.341 (4)	C10—C11	1.367 (6)
N2—H2'	0.885 (10)	C10—H10	0.9300
N3—C12	1.315 (5)	C11—H11	0.9300
N3—C11	1.325 (5)	C12—C13	1.373 (5)
C1—C2	1.384 (5)	C12—H12	0.9300
C1—C6	1.395 (5)	C13—H13	0.9300
C2—C3	1.357 (6)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.388 (6)	C14—H14C	0.9600
C4—O1—C14	118.0 (3)	N1—C7—H7	119.5
C1—O2—H2A	107 (3)	C6—C7—H7	119.5
H1A—O1S—H1B	106 (2)	O3—C8—N2	123.8 (3)
C7—N1—N2	116.7 (3)	O3—C8—C9	120.9 (3)
C8—N2—N1	118.5 (3)	N2—C8—C9	115.3 (3)
C8—N2—H2'	118 (3)	C13—C9—C10	117.7 (3)
N1—N2—H2'	122 (3)	C13—C9—C8	122.9 (3)
C12—N3—C11	116.3 (3)	C10—C9—C8	119.2 (3)
O2—C1—C2	117.9 (3)	C11—C10—C9	119.0 (4)
O2—C1—C6	123.1 (3)	C11—C10—H10	120.5
C2—C1—C6	118.9 (3)	C9—C10—H10	120.5
C3—C2—C1	121.3 (4)	N3—C11—C10	124.0 (4)
C3—C2—H2	119.3	N3—C11—H11	118.0
C1—C2—H2	119.3	C10—C11—H11	118.0
C2—C3—C4	120.2 (3)	N3—C12—C13	124.2 (4)
C2—C3—H3	119.9	N3—C12—H12	117.9
C4—C3—H3	119.9	C13—C12—H12	117.9
C5—C4—O1	125.1 (4)	C12—C13—C9	118.8 (3)
C5—C4—C3	119.8 (4)	C12—C13—H13	120.6
O1—C4—C3	115.1 (3)	C9—C13—H13	120.6
C4—C5—C6	120.5 (3)	O1—C14—H14A	109.5
C4—C5—H5	119.7	O1—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C1—C6—C5	119.2 (3)	O1—C14—H14C	109.5
C1—C6—C7	122.1 (3)	H14A—C14—H14C	109.5
C5—C6—C7	118.7 (3)	H14B—C14—H14C	109.5
N1—C7—C6	121.0 (3)
C7—N1—N2—C8	179.3 (3)	C1—C6—C7—N1	3.1 (5)
O2—C1—C2—C3	179.0 (4)	C5—C6—C7—N1	−176.8 (3)
C6—C1—C2—C3	−0.4 (6)	N1—N2—C8—O3	7.1 (6)
C1—C2—C3—C4	1.1 (6)	N1—N2—C8—C9	−170.4 (3)
C14—O1—C4—C5	−8.9 (7)	O3—C8—C9—C13	−144.0 (4)
C14—O1—C4—C3	171.8 (4)	N2—C8—C9—C13	33.6 (5)
C2—C3—C4—C5	−1.3 (6)	O3—C8—C9—C10	30.2 (6)
C2—C3—C4—O1	178.1 (4)	N2—C8—C9—C10	−152.3 (4)
O1—C4—C5—C6	−178.6 (4)	C13—C9—C10—C11	−0.2 (6)
C3—C4—C5—C6	0.7 (6)	C8—C9—C10—C11	−174.6 (4)
O2—C1—C6—C5	−179.5 (4)	C12—N3—C11—C10	−1.9 (7)
C2—C1—C6—C5	−0.1 (5)	C9—C10—C11—N3	1.6 (7)
O2—C1—C6—C7	0.6 (5)	C11—N3—C12—C13	0.9 (6)
C2—C1—C6—C7	180.0 (3)	N3—C12—C13—C9	0.4 (6)
C4—C5—C6—C1	0.0 (5)	C10—C9—C13—C12	−0.7 (5)
C4—C5—C6—C7	179.9 (3)	C8—C9—C13—C12	173.5 (3)
N2—N1—C7—C6	−177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O1Si	0.89 (1)	1.91 (1)	2.784 (4)	168 (4)
O1S—H1A···O3ii	0.86 (1)	1.92 (2)	2.764 (4)	170 (4)
O1S—H1B···N3iii	0.86 (1)	2.05 (2)	2.874 (5)	160 (4)
O2—H2A···N1	0.85 (1)	1.89 (3)	2.642 (4)	147 (4)
C11—H11···O1iv	0.93	2.46	3.370 (5)	164
C14—H14C···O3v	0.96	2.58	3.425 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O1S i	0.89 (1)	1.91 (1)	2.784 (4)	168 (4)
O1S—H1A⋯O3ii	0.86 (1)	1.92 (2)	2.764 (4)	170 (4)
O1S—H1B⋯N3iii	0.86 (1)	2.05 (2)	2.874 (5)	160 (4)
O2—H2A⋯N1	0.85 (1)	1.89 (3)	2.642 (4)	147 (4)
C11—H11⋯O1iv	0.93	2.46	3.370 (5)	164
C14—H14C⋯O3v	0.96	2.58	3.425 (5)	147

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