N′-[(E)-2-Hydroxy­benzyl­idene]-5-methyl­isoxazole-4-carbohydrazide monohydrate

Jin, Y.-X.; Yan, Z.-Z.; Yang, J.-G.; Zhong, A.-G.; Pan, F.-Y.

doi:10.1107/S1600536809048028

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3113

doi:10.1107/S1600536809048028

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N′-[(E)-2-Hydroxybenzylidene]-5-methylisoxazole-4-carbohydrazide monohydrate

Yan-Xian Jin,^a ^* Zhen-Zhong Yan,^a Jian-Guo Yang,^b Ai-Guo Zhong ^a and Fu-You Pan ^a

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China, and ^bOffice of Assets Administration, Taizhou University, Linhai 317000, People's Republic of China
^*Correspondence e-mail: snowflakej@gmail.com

(Received 28 October 2009; accepted 12 November 2009; online 18 November 2009)

In the structure of the title compound, C₁₂H₁₁N₃O₃·H₂O, the dihedral angle formed by the benzene and isoxazole rings is 2.03 (8)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond. In the crystal structure, molecules are linked into a three-dimesional network by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, and by π–π stacking interactions involving adjacent benzene and isoxazole rings [centroid–centroid separation = 3.663 (2) Å].

Related literature

For the biological and coordination properties of hydrazine compounds, see: Molina et al. (1994 ); Reiter et al. (1985 ); Sato et al. (1998 ); Edwards et al. (1975 ). For the pharmaceutical activity of isoxazole compounds, see: Stevens & Albizati (1984 ); El-Gaby et al. (2002 ). For the synthesis of the title compound, see: Jin et al. (2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₃·H₂O
M_r = 263.25
Orthorhombic, P n a 2₁
a = 12.8783 (6) Å
b = 11.3108 (6) Å
c = 8.6535 (4) Å
V = 1260.50 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.48 × 0.39 × 0.28 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.951, T_max = 0.971
12295 measured reflections
1432 independent reflections
1279 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 0.89
1432 reflections
182 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N3	0.87 (3)	1.890 (18)	2.617 (2)	145 (2)
N2—H2B⋯O1W	0.86	2.04	2.8847 (17)	169
O1W—H1W1⋯N1ⁱ	0.85 (3)	2.097 (15)	2.9304 (19)	166 (2)
O1W—H1W2⋯O2ⁱⁱ	0.831 (15)	1.955 (15)	2.7850 (17)	176 (2)
Symmetry codes: (i) $[-x, -y, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048028/rz2385sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048028/rz2385Isup2.hkl

checkCIF report

Comment top

The interest in the study of hydrazine compounds has recently grown due to their biological activities (Molina et al.1994; Sato et al.1998) and coordination ability (Reiter et al.1985; Edwards et al.1975). Isoxazole compounds have been widely studied because they exhibit some fungicidal activity, plant-growth regulating activity and antibacterial activity (Stevens et al.1984). Some isoxazole derivatives (El-Gaby et al.2002) are widely used as insecticides, herbicides and bactericides. However, compounds containing both the hydrazine and isoxazole groups has scarcely been reported. In order to search for more effective antibacterial medicines, we synthesized the title compound and report here its crystal structure.

The molecular structure of the title compounds is shown in Fig. 1. The molecule is almost planar, the dihedral angle between the benzene and the isoxazole rings being 2.03 (8)°. Bond lengths (Allen et al., 1987) and angles in the molecule are within normal ranges. The molecular conformation is enforced by an intramolecular O—H···N hydrogen bond (Table 1). In the crystal packing (Fig. 2), molecules are linked into supramolecular layers by intermolecular O—H···N and N—H···O hydrogen bonds, and by π–π stacking interactions involving adjacent benzene and isoxazole rings, with a centroid-to-centroid separation of 3.663 (2) Å. The layers are further linked by intermolecular O—H···O hydrogen bonds to form a three-dimensional network.

Related literature top

For the biological and coordination properties of hydrazine compounds, see: Molina et al. (1994); Reiter et al. (1985); Sato et al. (1998); Edwards et al. (1975). For the pharmaceutical activity of isoxazole compounds, see: Stevens & Albizati (1984); El-Gaby et al. (2002). For the synthesis of the title compound, see: Jin et al. (2008). For reference structural data, see: Allen et al. (1987).

Experimental top

The title compound, C₁₂H₁₃N₃O₄, was synthesized according to the literature method (Jin et al.2008). Salicylaldehyde (1.44 ml) was added into a solution of 5-methylisoxazole-4-carbonyl hydrazine (2.0 g, 0.014 mol) in anhydrous ethanol (40 ml). The mixture was refluxed for 2 h, then the precipitate was collected by filtration and washed with water, chloroform and ethanol. The product was recrystallized from ethanol, then dried under reduced pressure (yield 84.5%). Pink block-shaped crystals were obtained by slow evaporation of a dimethylformamide solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

N'-[(E)-2-Hydroxybenzylidene]-5-methylisoxazole-4-carbohydrazide monohydrate top

Crystal data top

C₁₂H₁₁N₃O₃·H₂O	F(000) = 552
M_r = 263.25	D_x = 1.387 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6440 reflections
a = 12.8783 (6) Å	θ = 2.4–27.0°
b = 11.3108 (6) Å	µ = 0.11 mm⁻¹
c = 8.6535 (4) Å	T = 296 K
V = 1260.50 (11) Å³	Block, pink
Z = 4	0.48 × 0.39 × 0.28 mm

Data collection top

Bruker APEXII area-detector diffractometer	1432 independent reflections
Radiation source: fine-focus sealed tube	1279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
T_min = 0.951, T_max = 0.971	k = −12→13
12295 measured reflections	l = −10→11

Refinement top

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0725P)² + 0.135P] where P = (F_o² + 2F_c²)/3
1432 reflections	(Δ/σ)_max = 0.097
182 parameters	Δρ_max = 0.14 e Å⁻³
5 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₂H₁₁N₃O₃·H₂O	V = 1260.50 (11) Å³
M_r = 263.25	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.8783 (6) Å	µ = 0.11 mm⁻¹
b = 11.3108 (6) Å	T = 296 K
c = 8.6535 (4) Å	0.48 × 0.39 × 0.28 mm

Data collection top

Bruker APEXII area-detector diffractometer	1432 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1279 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.971	R_int = 0.039
12295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	5 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.14 e Å⁻³
1432 reflections	Δρ_min = −0.14 e Å⁻³
182 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
N1	0.14390 (16)	−0.00283 (18)	0.3335 (3)	0.0565 (5)
N2	0.24031 (12)	0.15708 (15)	0.7518 (2)	0.0421 (4)
H2B	0.1744	0.1523	0.7368	0.051*
N3	0.27882 (14)	0.20055 (16)	0.8883 (2)	0.0416 (4)
O1W	0.01706 (11)	0.16789 (14)	0.7294 (2)	0.0559 (4)
H1W1	−0.026 (2)	0.123 (2)	0.776 (4)	0.084*
H1W2	−0.019 (2)	0.2255 (19)	0.704 (4)	0.084*
O1	0.24526 (12)	−0.01962 (14)	0.2774 (2)	0.0550 (4)
O2	0.40155 (10)	0.13200 (14)	0.6549 (2)	0.0517 (4)
O3	0.43156 (13)	0.25524 (19)	1.0747 (2)	0.0648 (5)
C1	0.26059 (14)	0.06858 (16)	0.5035 (3)	0.0373 (4)
C2	0.15530 (16)	0.0488 (2)	0.4659 (3)	0.0467 (5)
H2A	0.1002	0.0704	0.5294	0.056*
C3	0.31271 (16)	0.02328 (18)	0.3808 (3)	0.0442 (5)
C4	0.42389 (18)	0.0114 (3)	0.3423 (4)	0.0716 (8)
H4A	0.4309	−0.0251	0.2427	0.107*
H4B	0.4575	−0.0367	0.4189	0.107*
H4C	0.4555	0.0882	0.3404	0.107*
C5	0.30730 (14)	0.12213 (16)	0.6423 (3)	0.0376 (4)
C6	0.25002 (15)	0.27711 (17)	1.1395 (3)	0.0390 (4)
C7	0.35615 (16)	0.29084 (19)	1.1731 (3)	0.0443 (5)
C8	0.3861 (2)	0.3415 (2)	1.3120 (3)	0.0578 (6)
H8A	0.4563	0.3500	1.3347	0.069*
C9	0.3126 (2)	0.3794 (2)	1.4164 (3)	0.0583 (6)
H9A	0.3336	0.4143	1.5086	0.070*
C10	0.2090 (2)	0.3664 (2)	1.3859 (3)	0.0568 (6)
H10A	0.1598	0.3912	1.4576	0.068*
C11	0.17799 (17)	0.31606 (19)	1.2483 (3)	0.0488 (5)
H11A	0.1075	0.3080	1.2277	0.059*
C12	0.21445 (16)	0.22851 (18)	0.9941 (3)	0.0422 (5)
H12A	0.1437	0.2176	0.9776	0.051*
H3A	0.403 (2)	0.224 (2)	0.994 (3)	0.070 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0478 (11)	0.0662 (12)	0.0556 (12)	−0.0047 (9)	−0.0081 (9)	−0.0123 (11)
N2	0.0321 (8)	0.0543 (9)	0.0399 (9)	−0.0018 (7)	−0.0076 (7)	−0.0024 (8)
N3	0.0401 (8)	0.0488 (9)	0.0358 (9)	0.0008 (7)	−0.0086 (8)	−0.0013 (7)
O1W	0.0322 (7)	0.0646 (9)	0.0708 (11)	0.0027 (6)	0.0057 (8)	0.0108 (9)
O1	0.0562 (9)	0.0595 (9)	0.0491 (9)	−0.0023 (7)	0.0009 (8)	−0.0155 (8)
O2	0.0307 (7)	0.0630 (9)	0.0613 (10)	0.0010 (6)	−0.0087 (7)	−0.0070 (8)
O3	0.0354 (8)	0.1088 (15)	0.0502 (9)	0.0052 (8)	−0.0047 (7)	−0.0136 (11)
C1	0.0325 (9)	0.0358 (9)	0.0434 (10)	0.0001 (7)	−0.0015 (9)	0.0017 (8)
C2	0.0353 (10)	0.0559 (12)	0.0488 (12)	−0.0004 (8)	−0.0036 (9)	−0.0076 (10)
C3	0.0431 (11)	0.0424 (10)	0.0471 (12)	0.0001 (8)	0.0011 (10)	−0.0017 (9)
C4	0.0479 (13)	0.0867 (19)	0.080 (2)	0.0068 (12)	0.0167 (14)	−0.0125 (17)
C5	0.0350 (9)	0.0360 (9)	0.0420 (11)	0.0000 (7)	−0.0068 (8)	0.0030 (9)
C6	0.0377 (9)	0.0405 (9)	0.0388 (10)	0.0009 (7)	−0.0030 (8)	0.0058 (9)
C7	0.0386 (10)	0.0553 (11)	0.0390 (11)	0.0012 (8)	−0.0051 (9)	0.0017 (10)
C8	0.0486 (13)	0.0720 (16)	0.0528 (13)	−0.0036 (11)	−0.0138 (11)	−0.0078 (12)
C9	0.0750 (17)	0.0579 (14)	0.0420 (13)	0.0036 (11)	−0.0105 (12)	−0.0088 (11)
C10	0.0636 (15)	0.0623 (14)	0.0443 (12)	0.0138 (11)	0.0049 (12)	−0.0057 (11)
C11	0.0427 (10)	0.0545 (12)	0.0491 (12)	0.0040 (9)	0.0003 (11)	0.0015 (11)
C12	0.0355 (9)	0.0485 (11)	0.0426 (11)	−0.0002 (8)	−0.0068 (9)	0.0030 (9)

Geometric parameters (Å, º) top

N1—C2	1.294 (3)	C3—C4	1.476 (3)
N1—O1	1.405 (3)	C4—H4A	0.9600
N2—C5	1.341 (3)	C4—H4B	0.9600
N2—N3	1.372 (2)	C4—H4C	0.9600
N2—H2B	0.8600	C6—C11	1.393 (3)
N3—C12	1.274 (3)	C6—C7	1.406 (3)
O1W—H1W1	0.851 (17)	C6—C12	1.448 (3)
O1W—H1W2	0.831 (17)	C7—C8	1.386 (3)
O1—C3	1.338 (3)	C8—C9	1.377 (4)
O2—C5	1.224 (2)	C8—H8A	0.9300
O3—C7	1.353 (3)	C9—C10	1.368 (4)
O3—H3A	0.864 (18)	C9—H9A	0.9300
C1—C3	1.356 (3)	C10—C11	1.379 (4)
C1—C2	1.412 (3)	C10—H10A	0.9300
C1—C5	1.474 (3)	C11—H11A	0.9300
C2—H2A	0.9300	C12—H12A	0.9300

C2—N1—O1	105.15 (19)	O2—C5—C1	121.0 (2)
C5—N2—N3	118.78 (15)	N2—C5—C1	115.76 (15)
C5—N2—H2B	120.6	C11—C6—C7	118.2 (2)
N3—N2—H2B	120.6	C11—C6—C12	119.79 (19)
C12—N3—N2	118.15 (17)	C7—C6—C12	121.9 (2)
H1W1—O1W—H1W2	103 (2)	O3—C7—C8	118.0 (2)
C3—O1—N1	108.85 (18)	O3—C7—C6	122.3 (2)
C7—O3—H3A	109 (2)	C8—C7—C6	119.7 (2)
C3—C1—C2	103.6 (2)	C9—C8—C7	120.4 (2)
C3—C1—C5	126.24 (18)	C9—C8—H8A	119.8
C2—C1—C5	130.1 (2)	C7—C8—H8A	119.8
N1—C2—C1	112.6 (2)	C10—C9—C8	120.7 (2)
N1—C2—H2A	123.7	C10—C9—H9A	119.7
C1—C2—H2A	123.7	C8—C9—H9A	119.7
O1—C3—C1	109.82 (18)	C9—C10—C11	119.6 (2)
O1—C3—C4	116.5 (2)	C9—C10—H10A	120.2
C1—C3—C4	133.7 (2)	C11—C10—H10A	120.2
C3—C4—H4A	109.5	C10—C11—C6	121.4 (2)
C3—C4—H4B	109.5	C10—C11—H11A	119.3
H4A—C4—H4B	109.5	C6—C11—H11A	119.3
C3—C4—H4C	109.5	N3—C12—C6	120.83 (18)
H4A—C4—H4C	109.5	N3—C12—H12A	119.6
H4B—C4—H4C	109.5	C6—C12—H12A	119.6
O2—C5—N2	123.2 (2)

C5—N2—N3—C12	−176.93 (18)	C2—C1—C5—N2	0.6 (3)
C2—N1—O1—C3	0.1 (2)	C11—C6—C7—O3	179.8 (2)
O1—N1—C2—C1	0.2 (2)	C12—C6—C7—O3	−2.7 (3)
C3—C1—C2—N1	−0.3 (2)	C11—C6—C7—C8	0.3 (3)
C5—C1—C2—N1	−178.83 (19)	C12—C6—C7—C8	177.8 (2)
N1—O1—C3—C1	−0.3 (2)	O3—C7—C8—C9	179.9 (2)
N1—O1—C3—C4	179.0 (2)	C6—C7—C8—C9	−0.6 (4)
C2—C1—C3—O1	0.3 (2)	C7—C8—C9—C10	0.9 (4)
C5—C1—C3—O1	178.94 (17)	C8—C9—C10—C11	−0.8 (4)
C2—C1—C3—C4	−178.7 (3)	C9—C10—C11—C6	0.6 (4)
C5—C1—C3—C4	−0.1 (4)	C7—C6—C11—C10	−0.3 (3)
N3—N2—C5—O2	−3.5 (3)	C12—C6—C11—C10	−177.9 (2)
N3—N2—C5—C1	175.77 (16)	N2—N3—C12—C6	−178.73 (16)
C3—C1—C5—O2	1.7 (3)	C11—C6—C12—N3	174.73 (19)
C2—C1—C5—O2	179.9 (2)	C7—C6—C12—N3	−2.7 (3)
C3—C1—C5—N2	−177.57 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N3	0.87 (3)	1.89 (2)	2.617 (2)	145 (2)
N2—H2B···O1W	0.86	2.04	2.8847 (17)	169
O1W—H1W1···N1ⁱ	0.85 (3)	2.10 (2)	2.9304 (19)	166 (2)
O1W—H1W2···O2ⁱⁱ	0.83 (2)	1.96 (2)	2.7850 (17)	176 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₃·H₂O
M_r	263.25
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	12.8783 (6), 11.3108 (6), 8.6535 (4)
V (Å³)	1260.50 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.48 × 0.39 × 0.28

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.951, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	12295, 1432, 1279
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 0.89
No. of reflections	1432
No. of parameters	182
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N3	0.87 (3)	1.890 (18)	2.617 (2)	145 (2)
N2—H2B···O1W	0.86	2.04	2.8847 (17)	169.1
O1W—H1W1···N1ⁱ	0.85 (3)	2.097 (15)	2.9304 (19)	166 (2)
O1W—H1W2···O2ⁱⁱ	0.831 (15)	1.955 (15)	2.7850 (17)	176 (2)

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

Acknowledgements

The authors acknowledge financial support by the Zhejiang Provincial Natural Science Foundation of China (No.Y406049).

References

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Volume 65| Part 12| December 2009| Page o3113

doi:10.1107/S1600536809048028

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

N′-[(E)-2-Hy­droxy­benzyl­­idene]-5-methyl­isoxazole-4-carbohydrazide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-2-Hydroxybenzylidene]-5-methylisoxazole-4-carbohydrazide monohydrate