N′-{(E)-[5-(Hy­droxy­meth­yl)furan-2-yl]methyl­idene}pyridine-4-carbohydrazide dihydrate

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

doi:10.1107/S1600536813020114

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1342-o1343

doi:10.1107/S1600536813020114

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N′-{(E)-[5-(Hydroxymethyl)furan-2-yl]methylidene}pyridine-4-carbohydrazide dihydrate

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 30 June 2013; accepted 20 July 2013; online 27 July 2013)

In the title compound, C₁₂H₁₁N₃O₃·2H₂O, the dihedral angle formed by the planes of the pyridine and the furan rings of the organic carbohydrazide molecule is 4.66 (7)°. In the crystal, these molecules form stacks along the b-axis direction, neighbouring molecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine and furan rings being 3.714 (1) Å. Molecules from neighboring stacks are linked by pairs of N—H⋯O hydrogen bonds. The water molecules fill the channels between the stacks being linked by O—H⋯O hydrogen bonds into helices along [010]. Besides this, water molecules are involved in O—H⋯N and O—H⋯O hydrogen bonds with the carbohydrazide molecules, thus forming a three-dimensional network, augmented by weak C—H⋯O interactions.

Related literature

For biological properties of carbohydrazide and its derivatives, see: Rollas & Kucukguzel (2007 ); Bakir & Brown (2002 ). For the synthesis of related compounds, see: Sreeja & Kurup (2005 ). For related structures, see: Nair et al. (2012 ); Reshma et al. (2012 ); Prasanna et al. (2013 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₃·2H₂O
M_r = 281.27
Monoclinic, P 2₁ /c
a = 10.7020 (14) Å
b = 7.0263 (8) Å
c = 18.024 (3) Å
β = 106.252 (7)°
V = 1301.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.50 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.946, T_max = 0.972
9681 measured reflections
3139 independent reflections
2308 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.114
S = 1.03
3139 reflections
206 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2S—H2A⋯N3	0.85 (2)	2.49 (2)	3.2272 (17)	146 (2)
O2S—H2A⋯O1	0.85 (2)	2.22 (2)	2.9648 (15)	146 (2)
O3—H3′⋯O1Sⁱ	0.89 (2)	1.90 (2)	2.7937 (16)	174.9 (18)
O2S—H2B⋯O1Sⁱⁱ	0.86 (2)	2.06 (2)	2.9145 (18)	171 (2)
O1S—H1B⋯O2Sⁱⁱⁱ	0.87 (2)	1.94 (2)	2.7924 (17)	167 (2)
N2—H2′⋯O3^iv	0.876 (18)	2.024 (18)	2.8485 (16)	156.3 (16)
O1S—H1A⋯N1	0.87 (2)	2.03 (2)	2.8501 (16)	157 (2)
C4—H4⋯O3^iv	0.93	2.50	3.3897 (18)	160
C12—H12B⋯O1^v	0.97	2.43	3.3621 (19)	162
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+2, -z+2; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536813020114/yk2097sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020114/yk2097Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020114/yk2097Isup3.cml

checkCIF report

Comment top

Heterocyclic carbohydrazides are compounds with a wide spectrum of biological and analytical applications. They form stable metal chelates which find applications in molecular sensing (Bakir & Brown, 2002). The title compound is a derivative of isoniazid which is one of the first line drug used in the treatment of tuberculosis. A number of hydrazones derived from isoniazid were reported to be active antitubercular agents and were found to be less toxic than isoniazid (Rollas & Kucukguzel, 2007).

The compound crystallizes in monoclinic P2₁/c space group. The molecule exists in a E configuration with respect to the C7=N3 bond, typical of such kind of compounds (Reshma et al., 2012), with the C8—C7—N3—N2 torsion angle of 178.04 (11)° (Fig 1). The N3—N2—C6—O1 torsion angle of -2.72 (18)° indicates the cis configuration of the O1 atom with respect to the hydrazine nitrogen atom N3 (Nair et al., 2012). C7═N3 [1.267 (3) Å] and C6═O1 [1.217 (8) Å] bond distances are very close to the formal double C═N and C═O bond lengths (Prasanna, et al., 2013) confirming that the carbohydrazide exists in solid state as an amido tautomer.

Seven classical hydrogen bonds are present in the crystal (Fig. 2). One of the nitrogen atoms of pyridine-4-carbohydrazide molecule is involved in classical intermolecular hydrogen bond of the N—H···O type with oxygen atom of the hydroxymethyl group of the neighboring molecule with a D···A distance of 2.8483 (16) Å. There are two hydrogen bonds of the O—H···O type between the two water molecules: O2S—H2B···O1S and O1S—H1B···O2S with D···A distances of 2.9146 (18) Å and 2.7923 (17) Å, respectively. Each water molecule is involved in other O—H···O and O—H···N hydrogen bonds: O2S—H2A···O1 and O3—H3'···O1S with D···A distances of 2.9647 (15) Å and 2.7937 (16) Å and O2S—H2A···N3 and O1S—H1A···N1 with D···A distances of 3.2272 (17) Å and 2.8501 (16) Å, respectively. Additionally, there are non-classical intermolecular C—H···O hydrogen bonds between the hydrogen atoms attached to C4 and C12 carbon atoms and the O3 and O1 atoms of the neighboring molecule with D···A distances of 3.390 (2) Å and 3.362 (2) Å, respectively. These interactions are augmented by weak π···π interactions which connect the molecules with a centroid-centroid distances of 3.714 (1) Å and 3.760 (1) Å (Fig. 3). The packing diagram showing the molecular assembly of the title compound along the b axis is shown in Fig. 4.

Related literature top

For biological properties of carbohydrazide and its derivatives, see: Rollas & Kucukguzel (2007); Bakir & Brown (2002). For the synthesis of related compounds, see: Sreeja & Kurup (2005). For related structures, see: Nair et al. (2012); Reshma et al. (2012); Prasanna et al. (2013).

Experimental top

The title compound was prepared by adapting a reported procedure (Sreeja & Kurup, 2005). To a warm methanolic solution of 5-(hydroxymethyl)furan-2-carbaldehyde (0.126 g, 1 mmol), a methanolic solution of pyridine-4-carbohydrazide (0.137 g, 1 mmol) was added and the resulting solution was stirred well with slight heating for 75 minutes. A colorless compound formed was filtered off, washed with water, ethanol and finally with ether and dried. Single crystals suitable for X-ray diffraction studies were obtained by recrystallization from a mixture of methanol, ethanol and DMF.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of the structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids for the non-H atoms drawn at the 50% probability level.
	Fig. 2. Hydrogen bonding in the crystal of the title compound.
	Fig. 3. The π···π stacking interactions in the title compound.
	Fig. 4. A view of the unit cell along the b axis.

N'-{(E)-[5-(Hydroxymethyl)furan-2-yl]methylidene}pyridine-4-carbohydrazide dihydrate top

Crystal data top

C₁₂H₁₁N₃O₃·2H₂O	F(000) = 592
M_r = 281.27	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3182 reflections
a = 10.7020 (14) Å	θ = 2.4–28.2°
b = 7.0263 (8) Å	µ = 0.11 mm⁻¹
c = 18.024 (3) Å	T = 296 K
β = 106.252 (7)°	Block, colorless
V = 1301.2 (3) Å³	0.50 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3139 independent reflections
Radiation source: fine-focus sealed tube	2308 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.0°, θ_min = 3.1°
ω and ϕ scan	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −9→9
T_min = 0.946, T_max = 0.972	l = −23→16
9681 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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0564P)² + 0.1806P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3139 reflections	Δρ_max = 0.23 e Å⁻³
206 parameters	Δρ_min = −0.19 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: 0.0056 (14)

Crystal data top

C₁₂H₁₁N₃O₃·2H₂O	V = 1301.2 (3) Å³
M_r = 281.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7020 (14) Å	µ = 0.11 mm⁻¹
b = 7.0263 (8) Å	T = 296 K
c = 18.024 (3) Å	0.50 × 0.25 × 0.25 mm
β = 106.252 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3139 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2308 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.972	R_int = 0.023
9681 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	6 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
3139 reflections	Δρ_min = −0.19 e Å⁻³
206 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O2	0.65878 (8)	0.90209 (13)	1.02711 (5)	0.0361 (2)
N3	0.59249 (10)	0.91380 (15)	0.82424 (6)	0.0352 (3)
N1	0.17508 (11)	0.89401 (16)	0.49077 (6)	0.0405 (3)
N2	0.48334 (11)	0.90481 (16)	0.76219 (6)	0.0340 (3)
O3	0.74289 (10)	1.09936 (16)	1.18406 (6)	0.0456 (3)
O1	0.60410 (9)	0.97315 (16)	0.68198 (6)	0.0459 (3)
O1S	0.05219 (11)	0.82845 (18)	0.33090 (6)	0.0484 (3)
O2S	0.87042 (11)	0.96561 (18)	0.78948 (7)	0.0553 (3)
C1	0.40194 (13)	0.8935 (2)	0.55313 (8)	0.0379 (3)
H1	0.4862	0.8853	0.5486	0.046*
C5	0.38137 (12)	0.91494 (16)	0.62455 (7)	0.0291 (3)
C4	0.25460 (13)	0.9228 (2)	0.62766 (8)	0.0382 (3)
H4	0.2358	0.9350	0.6748	0.046*
C2	0.29770 (15)	0.8844 (2)	0.48870 (8)	0.0427 (3)
H2	0.3138	0.8708	0.4409	0.051*
C3	0.15595 (13)	0.9122 (2)	0.55978 (8)	0.0421 (3)
H3	0.0706	0.9181	0.5626	0.051*
C7	0.57428 (13)	0.89688 (18)	0.89043 (8)	0.0353 (3)
H7	0.4906	0.8833	0.8955	0.042*
C8	0.68443 (13)	0.89898 (17)	0.95717 (7)	0.0328 (3)
C11	0.77674 (13)	0.90344 (18)	1.08159 (7)	0.0348 (3)
C10	0.87211 (14)	0.8998 (2)	1.04728 (9)	0.0439 (4)
H10	0.9610	0.8996	1.0719	0.053*
C12	0.77600 (15)	0.9152 (2)	1.16286 (8)	0.0441 (4)
H12B	0.7141	0.8236	1.1719	0.053*
H12A	0.8615	0.8810	1.1956	0.053*
C9	0.81354 (14)	0.8965 (2)	0.96715 (9)	0.0437 (3)
H9	0.8559	0.8931	0.9286	0.052*
C6	0.49926 (12)	0.93343 (17)	0.69202 (7)	0.0304 (3)
H1A	0.067 (2)	0.853 (3)	0.3797 (9)	0.089 (7)*
H2'	0.4086 (18)	0.875 (2)	0.7700 (10)	0.058 (5)*
H1B	−0.0138 (16)	0.751 (3)	0.3174 (11)	0.077 (6)*
H2B	0.888 (2)	1.017 (3)	0.7503 (11)	0.094 (8)*
H3'	0.808 (2)	1.176 (3)	1.1820 (11)	0.075 (6)*
H2A	0.7875 (15)	0.961 (3)	0.7772 (12)	0.083 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0314 (5)	0.0508 (5)	0.0229 (5)	−0.0029 (4)	0.0023 (4)	0.0017 (4)
N3	0.0323 (6)	0.0432 (6)	0.0257 (6)	−0.0023 (4)	0.0009 (5)	−0.0009 (4)
N1	0.0406 (7)	0.0478 (7)	0.0282 (6)	−0.0018 (5)	0.0016 (5)	−0.0017 (5)
N2	0.0276 (6)	0.0488 (6)	0.0224 (6)	−0.0037 (5)	0.0019 (5)	0.0008 (4)
O3	0.0446 (6)	0.0623 (7)	0.0327 (6)	−0.0122 (5)	0.0156 (5)	−0.0072 (4)
O1	0.0300 (5)	0.0750 (7)	0.0327 (5)	−0.0025 (5)	0.0089 (4)	0.0011 (5)
O1S	0.0448 (6)	0.0656 (7)	0.0315 (6)	−0.0005 (5)	0.0052 (5)	−0.0008 (5)
O2S	0.0374 (6)	0.0725 (8)	0.0497 (7)	0.0006 (5)	0.0019 (5)	0.0059 (6)
C1	0.0339 (7)	0.0518 (8)	0.0293 (7)	0.0009 (6)	0.0107 (6)	−0.0013 (5)
C5	0.0307 (6)	0.0311 (6)	0.0241 (6)	0.0005 (5)	0.0053 (5)	0.0013 (4)
C4	0.0344 (7)	0.0559 (8)	0.0247 (7)	0.0008 (6)	0.0088 (5)	0.0010 (5)
C2	0.0474 (8)	0.0551 (8)	0.0246 (7)	−0.0006 (6)	0.0086 (6)	−0.0048 (6)
C3	0.0317 (7)	0.0582 (9)	0.0334 (8)	−0.0005 (6)	0.0042 (6)	0.0006 (6)
C7	0.0333 (7)	0.0427 (7)	0.0271 (7)	−0.0013 (5)	0.0040 (5)	0.0007 (5)
C8	0.0363 (7)	0.0372 (6)	0.0233 (6)	−0.0017 (5)	0.0058 (5)	−0.0013 (5)
C11	0.0326 (7)	0.0378 (7)	0.0279 (7)	−0.0010 (5)	−0.0018 (5)	0.0012 (5)
C10	0.0327 (7)	0.0562 (9)	0.0377 (8)	0.0011 (6)	0.0010 (6)	−0.0092 (6)
C12	0.0474 (8)	0.0527 (8)	0.0255 (7)	−0.0084 (6)	−0.0006 (6)	0.0065 (6)
C9	0.0369 (7)	0.0594 (9)	0.0347 (8)	−0.0013 (6)	0.0100 (6)	−0.0095 (6)
C6	0.0289 (6)	0.0350 (6)	0.0264 (6)	0.0022 (5)	0.0065 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

O2—C8	1.3634 (15)	C1—H1	0.9300
O2—C11	1.3654 (15)	C5—C4	1.3745 (18)
N3—C7	1.2671 (17)	C5—C6	1.4928 (17)
N3—N2	1.3741 (15)	C4—C3	1.3763 (18)
N1—C3	1.3221 (17)	C4—H4	0.9300
N1—C2	1.3248 (19)	C2—H2	0.9300
N2—C6	1.3379 (16)	C3—H3	0.9300
N2—H2'	0.876 (18)	C7—C8	1.4294 (18)
O3—C12	1.4218 (18)	C7—H7	0.9300
O3—H3'	0.89 (2)	C8—C9	1.3427 (19)
O1—C6	1.2178 (15)	C11—C10	1.333 (2)
O1S—H1A	0.865 (16)	C11—C12	1.4694 (19)
O1S—H1B	0.872 (15)	C10—C9	1.405 (2)
O2S—H2B	0.860 (16)	C10—H10	0.9300
O2S—H2A	0.853 (15)	C12—H12B	0.9700
C1—C2	1.3683 (19)	C12—H12A	0.9700
C1—C5	1.3737 (18)	C9—H9	0.9300

C8—O2—C11	106.27 (10)	N3—C7—C8	118.91 (12)
C7—N3—N2	116.25 (11)	N3—C7—H7	120.5
C3—N1—C2	116.53 (12)	C8—C7—H7	120.5
C6—N2—N3	117.28 (11)	C9—C8—O2	110.02 (11)
C6—N2—H2'	123.5 (12)	C9—C8—C7	133.47 (13)
N3—N2—H2'	119.1 (12)	O2—C8—C7	116.50 (11)
C12—O3—H3'	106.2 (12)	C10—C11—O2	109.88 (12)
H1A—O1S—H1B	108.4 (18)	C10—C11—C12	132.98 (13)
H2B—O2S—H2A	104.8 (19)	O2—C11—C12	117.09 (12)
C2—C1—C5	119.61 (12)	C11—C10—C9	107.34 (13)
C2—C1—H1	120.2	C11—C10—H10	126.3
C5—C1—H1	120.2	C9—C10—H10	126.3
C1—C5—C4	117.48 (12)	O3—C12—C11	112.99 (11)
C1—C5—C6	116.89 (11)	O3—C12—H12B	109.0
C4—C5—C6	125.60 (11)	C11—C12—H12B	109.0
C5—C4—C3	118.81 (12)	O3—C12—H12A	109.0
C5—C4—H4	120.6	C11—C12—H12A	109.0
C3—C4—H4	120.6	H12B—C12—H12A	107.8
N1—C2—C1	123.54 (13)	C8—C9—C10	106.49 (13)
N1—C2—H2	118.2	C8—C9—H9	126.8
C1—C2—H2	118.2	C10—C9—H9	126.8
N1—C3—C4	124.02 (13)	O1—C6—N2	122.77 (12)
N1—C3—H3	118.0	O1—C6—C5	120.18 (11)
C4—C3—H3	118.0	N2—C6—C5	117.05 (11)

C7—N3—N2—C6	176.19 (11)	C8—O2—C11—C12	177.41 (11)
C2—C1—C5—C4	1.17 (19)	O2—C11—C10—C9	0.14 (16)
C2—C1—C5—C6	−177.08 (12)	C12—C11—C10—C9	−177.28 (15)
C1—C5—C4—C3	−1.08 (19)	C10—C11—C12—O3	103.43 (18)
C6—C5—C4—C3	177.01 (12)	O2—C11—C12—O3	−73.84 (15)
C3—N1—C2—C1	−0.4 (2)	O2—C8—C9—C10	−0.54 (16)
C5—C1—C2—N1	−0.4 (2)	C7—C8—C9—C10	−179.70 (14)
C2—N1—C3—C4	0.5 (2)	C11—C10—C9—C8	0.25 (17)
C5—C4—C3—N1	0.2 (2)	N3—N2—C6—O1	−2.72 (18)
N2—N3—C7—C8	178.04 (11)	N3—N2—C6—C5	177.35 (10)
C11—O2—C8—C9	0.62 (14)	C1—C5—C6—O1	16.96 (17)
C11—O2—C8—C7	179.94 (11)	C4—C5—C6—O1	−161.14 (13)
N3—C7—C8—C9	−8.1 (2)	C1—C5—C6—N2	−163.11 (12)
N3—C7—C8—O2	172.79 (11)	C4—C5—C6—N2	18.79 (18)
C8—O2—C11—C10	−0.46 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2S—H2A···N3	0.85 (2)	2.49 (2)	3.2272 (17)	146 (2)
O2S—H2A···O1	0.85 (2)	2.22 (2)	2.9648 (15)	146 (2)
O3—H3′···O1Sⁱ	0.89 (2)	1.90 (2)	2.7937 (16)	174.9 (18)
O2S—H2B···O1Sⁱⁱ	0.86 (2)	2.06 (2)	2.9145 (18)	171 (2)
O1S—H1B···O2Sⁱⁱⁱ	0.87 (2)	1.94 (2)	2.7924 (17)	167 (2)
N2—H2′···O3^iv	0.876 (18)	2.024 (18)	2.8485 (16)	156.3 (16)
O1S—H1A···N1	0.87 (2)	2.03 (2)	2.8501 (16)	157 (2)
C4—H4···O3^iv	0.93	2.50	3.3897 (18)	160
C12—H12B···O1^v	0.97	2.43	3.3621 (19)	162

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2S—H2A···N3	0.853 (15)	2.485 (17)	3.2272 (17)	146.0 (19)
O2S—H2A···O1	0.853 (15)	2.219 (18)	2.9648 (15)	146.1 (19)
O3—H3'···O1Sⁱ	0.89 (2)	1.90 (2)	2.7937 (16)	174.9 (18)
O2S—H2B···O1Sⁱⁱ	0.860 (16)	2.063 (16)	2.9145 (18)	171 (2)
O1S—H1B···O2Sⁱⁱⁱ	0.872 (15)	1.936 (15)	2.7924 (17)	166.9 (19)
N2—H2'···O3^iv	0.876 (18)	2.024 (18)	2.8485 (16)	156.3 (16)
O1S—H1A···N1	0.865 (16)	2.033 (17)	2.8501 (16)	157 (2)
C4—H4···O3^iv	0.93	2.50	3.3897 (18)	160
C12—H12B···O1^v	0.97	2.43	3.3621 (19)	162

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

Acknowledgements

MKP is thankful to the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK is thankful to 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 single-crystal X-ray diffraction measurements.

References

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Volume 69| Part 8| August 2013| Pages o1342-o1343

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-{(E)-[5-(Hy­dr­oxy­meth­yl)furan-2-yl]methyl­­idene}pyridine-4-carbohydrazide dihydrate

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N′-{(E)-[5-(Hydroxymethyl)furan-2-yl]methylidene}pyridine-4-carbohydrazide dihydrate