(E)-Methyl N′-(3-hy­droxy­benzyl­idene)hydrazinecarboxyl­ate dihydrate

Wei-Wei Li; Tie-Ming Yu; Lu-Ping Lv; Xian-Chao Hu

doi:10.1107/S1600536811035689

. 2011 Sep 14;67(Pt 10):o2584. doi: 10.1107/S1600536811035689

(E)-Methyl N′-(3-hydroxybenzylidene)hydrazinecarboxylate dihydrate

Wei-Wei Li ^a, Tie-Ming Yu ^a, Lu-Ping Lv ^a, Xian-Chao Hu ^b,^c,^*

PMCID: PMC3201241 PMID: 22058745

Abstract

The title compound, C₉H₁₀N₂O₃·2H₂O, crystallizes with two organic molecules and four water molecules in the asymmetric unit. Both organic molecules adopt a trans conformation with respect to the C=N bond and are close to planar [dihedral angles between the side chain and the aromatic ring = 9.34 (8) and 4.96 (8)°]. In the crystal, the components are linked into three-dimensional network by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For background to benzaldehydehydrazone derivatives, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶); Borg et al. (1999 ▶). For a related structure, see: Shang et al. (2007 ▶).

Experimental

Crystal data

C₉H₁₀N₂O₃·2H₂O
M _r = 230.22
Monoclinic,
a = 11.7316 (16) Å
b = 20.785 (3) Å
c = 9.5259 (16) Å
β = 99.675 (3)°
V = 2289.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 223 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.977, T _max = 0.989
19583 measured reflections
4438 independent reflections
3346 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.117
S = 1.03
4438 reflections
326 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035689/hb6397sup1.cif

e-67-o2584-sup1.cif^{(22KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035689/hb6397Isup2.hkl

e-67-o2584-Isup2.hkl^{(213KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1B⋯O2W	0.85 (3)	2.02 (3)	2.859 (2)	169 (2)
O1W—H1A⋯O2Wⁱ	0.86 (3)	1.95 (3)	2.809 (3)	172 (3)
N2—H2⋯O6ⁱⁱ	0.86	2.07	2.9278 (17)	171
O2W—H2A⋯O4ⁱⁱⁱ	1.02 (3)	1.88 (3)	2.893 (2)	171 (3)
O2W—H2B⋯O1	0.81 (3)	2.23 (3)	2.9102 (18)	141 (3)
O2W—H2B⋯N1	0.81 (3)	2.59 (3)	3.322 (2)	149 (3)
O3W—H3A⋯O4^iv	0.88 (3)	2.15 (3)	2.877 (2)	139 (3)
O3W—H3B⋯O1^v	0.95 (3)	1.90 (3)	2.832 (2)	168 (3)
O3—H3W⋯O1W	0.82	1.93	2.6617 (19)	147
O4W—H4B⋯O3Wⁱⁱⁱ	0.87 (3)	2.00 (3)	2.864 (2)	172 (2)
O4W—H4A⋯O3W^vi	0.82 (4)	2.20 (4)	3.013 (3)	170 (3)
N4—H4N⋯O3^vii	0.86	2.10	2.9509 (18)	169
O6—H6⋯O4W	0.92 (3)	1.75 (3)	2.665 (2)	176 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Acknowledgments

The authors thank Hangzhou Vocational and Technical College, China, for financial support.

supplementary crystallographic information

Comment

Benzaldehydehydrazone derivatives have received considerable attentions for a long time due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties(Hadjoudis et al., 1987). Meanwhile, it's an important intermidiate of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many properties(Borg et al., 1999). As a further investigation of this type of derivatives, we report herein the crystal structure of the title compound, (I).

The title compound, C₉H₁₀N₂O₃ .2H₂O, crystallizes with two very similar independent molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O1/O2/C7-C9 and N3/N4/O4/O5/C16-C18 planes form dihedral angles of 9.34 (8)° and 4.96 (8)°, respectively, with the C1—C6 and C10—C15 planes. The bond lengths and angles of the main molecule agree with those observed for (E)-Methyl N'-(4-hydroxybenzylidene)hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, Intramolecular O—H···N and O—H···O hydrogen bonds are observed in each independent molecule. molecules are linked into three-dimensional network by N—H···O and O—H···Ohydrogen bonds (Table 1, Fig.2).

Experimental

3-Hydroxybenzaldehyde (1.22g, 0.01mol) and methyl hydrazinecarboxylate(0.9g, 0.01mol) were dissolved in stirred methanol (30ml) and left for 2h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 90% yield. Colourless blocks of (I) were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 418-421 K).