N'-{(E)-[5-(Hy-droxy-meth-yl)furan-2-yl]methyl-idene}pyridine-4-carbohydrazide dihydrate.

In the title compound, C12H11N3O3·2H2O, the dihedral angle formed by the planes of the pyridine and the furan rings of the organic carbohydrazide mol-ecule is 4.66 (7)°. In the crystal, these mol-ecules form stacks along the b-axis direction, neighbouring mol-ecules 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. Mol-ecules from neighboring stacks are linked by pairs of N-H⋯O hydrogen bonds. The water mol-ecules fill the channels between the stacks being linked by O-H⋯O hydrogen bonds into helices along [010]. Besides this, water mol-ecules are involved in O-H⋯N and O-H⋯O hydrogen bonds with the carbohydrazide mol-ecules, 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 = 281.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.114

S = 1.03

3139 reflections

206 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813020114/yk2097sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020114/yk2097Isup3.cml

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

C12H11N3O3·2H2O	F(000) = 592
Mr = 281.27	Dx = 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

Bruker Kappa APEXII CCD diffractometer	3139 independent reflections
Radiation source: fine-focus sealed tube	2308 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm-1	θmax = 28.0°, θmin = 3.1°
ω and φ scan	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −9→9
Tmin = 0.946, Tmax = 0.972	l = −23→16
9681 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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1806P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3139 reflections	Δρmax = 0.23 e Å−3
206 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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′···O3iv	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···O3iv	0.93	2.50	3.3897 (18)	160
C12—H12B···O1v	0.97	2.43	3.3621 (19)	162

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′⋯O1S i	0.89 (2)	1.90 (2)	2.7937 (16)	174.9 (18)
O2S—H2B⋯O1S ii	0.86 (2)	2.06 (2)	2.9145 (18)	171 (2)
O1S—H1B⋯O2S iii	0.87 (2)	1.94 (2)	2.7924 (17)	167 (2)
N2—H2′⋯O3iv	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⋯O3iv	0.93	2.50	3.3897 (18)	160
C12—H12B⋯O1v	0.97	2.43	3.3621 (19)	162

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