N′-[(E)-2-Hy­droxy-5-meth­oxy­benzyl­idene]pyridine-4-carbohydrazide monohydrate

Prasanna, M.K.; Sithambaresan, M.; Pradeepkumar, K.; Kurup, M.R.P.

doi:10.1107/S160053681301235X

organic compounds

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Volume 69| Part 6| June 2013| Page o881

doi:10.1107/S160053681301235X

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N′-[(E)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate

M. K. Prasanna,^a M. Sithambaresan,^b ^* K. Pradeepkumar ^a and M. R. Prathapachandra Kurup ^c

^aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
^*Correspondence e-mail: eesans@yahoo.com

(Received 14 April 2013; accepted 6 May 2013; online 15 May 2013)

The title compound, C₁₄H₁₃N₃O₃·H₂O, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. An intramolecular 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 interactions. The structure also features two non-classical C—H⋯O interactions.

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_r = 289.29
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.00
1668 reflections
208 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O1^iv	0.93	2.46	3.370 (5)	164
C14—H14C⋯O3^v	0.96	2.58	3.425 (5)	147
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{3\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301235X/fj2628sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681301235X/fj2628Isup3.cml

checkCIF report

Comment top

Derivatives of carbohydrazide and their metal complexes exhibit prominent biological activities and versatile binding properties. They also promote the formation of a chelate binding center (Mangalam & Kurup, 2011). Versatile applications in molecular sensing of metals have received substantial interest during the last decade (Bakir & Brown, 2002).

The compound crystallizes in orthorhombic Pna2₁ space group. The molecule exists in the E configuration with respect to C7=N1 bond (Sithambaresan & Kurup, 2011) which is confirmed by the torsion angle of -177.6 (3)° of C6—C7—N1—N2 moiety (Fig. 1). The torsion angle of 7.2 (5)° corresponding to N1—N2—C8—O3 moiety supports the cis configuration of the O3 atom with respect to the hydrazine nitrogen atom N1 (Kargar et al., 2010; Shafiq et al., 2009). The C7=N1 [1.272 (4) Å] and C8=O3 [1.219 (3) Å] bond distances are very close to the formal C=N and C=O bond lengths [C=N; 1.28 Å and C═O; 1.21 Å] respectively confirming the azomethine bond formation and the existence of carbohydrazide in amido form in solid state.

Incorporation of water molecule in the crystal system of the title compound plays an important role in assembly of the molecules in the lattice through intermolecular hydrogen bonds and makes the crystal system entirely different from the reported one (Kargar et al., 2010). Two classical hydrogen bonds are present in the molecular system (Fig. 2) between the both H atoms of the water molecule and O3 and N3 atoms of the neighbouring molecules with a D···A distances of 2.764 (4) and 2.874 (5) Å respectively. The phenolic oxygen O2 is involved in an intramolecular hydrogen bond with N1 to form a six membered ring. The hydrazinic nitrogen N2 is also involved in hydrogen bonding with oxygen of solvent water. Two non- classical C–H···O hydrogen bonds are also present in the molecule (Table 1). The packing diagram showing the molecular assembly of the title compound along a axis is shown in Fig. 3.

Related literature top

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 top

The title compound was prepared by adapting a reported procedure (Mangalam et al., 2009). To a warm ethanolic solution of 2-hydroxy-5-methoxybenzaldehyde (0.152 g, 1 mmol), a methanolic solution of pyridine-4-carbohydrazide (0.137 g, 1 mmol) was added and the resulting solution was refluxed for 45 minutes after adding 3 drops of glacial acetic acid. On cooling the solution, yellow crystals separated out. Single crystals suitable for X-ray diffraction studies were obtained by slow evaporation of its solution in 1:1 mixture of ethanol and DMF.

Computing details top

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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Graphical representation showing hydrogen bondings in the crystal structure of C₁₄H₁₃N₃O₃.H₂O.
	Fig. 3. A view of the unit cell along a axis.

N'-[(E)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate top

Crystal data top

C₁₄H₁₃N₃O₃·H₂O	F(000) = 608
M_r = 289.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0701P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1668 reflections	Δρ_max = 0.17 e Å⁻³
208 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₁₃N₃O₃·H₂O	V = 1439.0 (3) Å³
M_r = 289.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.6455 (16) Å	µ = 0.10 mm⁻¹
b = 12.7423 (16) Å	T = 296 K
c = 8.9306 (9) Å	0.40 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1668 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1134 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.976	R_int = 0.056
10294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	6 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
1668 reflections	Δρ_min = −0.15 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.46	3.370 (5)	164
C14—H14C···O3^v	0.96	2.58	3.425 (5)	147

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z; (iii) −x+1, −y, z−1/2; (iv) −x+1/2, y−1/2, z+3/2; (v) −x+1/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₃·H₂O
M_r	289.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	12.6455 (16), 12.7423 (16), 8.9306 (9)
V (Å³)	1439.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.965, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	10294, 1668, 1134
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.00
No. of reflections	1668
No. of parameters	208
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2'···O1Sⁱ	0.885 (10)	1.912 (14)	2.784 (4)	168 (4)
O1S—H1A···O3ⁱⁱ	0.856 (10)	1.918 (15)	2.764 (4)	170 (4)
O1S—H1B···N3ⁱⁱⁱ	0.859 (10)	2.050 (17)	2.874 (5)	160 (4)
O2—H2A···N1	0.847 (10)	1.89 (3)	2.642 (4)	147 (4)
C11—H11···O1^iv	0.93	2.46	3.370 (5)	164
C14—H14C···O3^v	0.96	2.58	3.425 (5)	147

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z; (iii) −x+1, −y, z−1/2; (iv) −x+1/2, y−1/2, z+3/2; (v) −x+1/2, y+1/2, z−1/2.

Acknowledgements

MKP thanks the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK thanks the UGC, New Delhi, for a UGC–BSR one-time grant to Faculty. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the data collection.

References

Bakir, M. & Brown, O. (2002). J. Mol. Struct. 609, 129–136. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kargar, H., Kia, R., Akkurt, M. & Büyükgüngör, O. (2010). Acta Cryst. E66, o2982. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 76, 22–28. Google Scholar
Mangalam, N. A., Sivakumar, S., Sheeja, S. R., Kurup, M. R. P. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 4191–4197. Web of Science CSD CrossRef CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(E)-2-Hy­dr­oxy-5-meth­­oxy­benzyl­­idene]pyridine-4-carbohydrazide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-2-Hydroxy-5-methoxybenzylidene]pyridine-4-carbohydrazide monohydrate