2-Hydr­oxy-N′-(4-isopropyl­cyclo­hexyl­carbon­yl)-3-methyl­benzohydrazide

Tian-Pin Shu; Jun-Long Wen; Su-Zhen Chen; Ke-Wei Lei

doi:10.1107/S160053680900556X

. 2009 Feb 21;65(Pt 3):o575. doi: 10.1107/S160053680900556X

2-Hydroxy-N′-(4-isopropylcyclohexylcarbonyl)-3-methylbenzohydrazide

Tian-Pin Shu ^a, Jun-Long Wen ^a, Su-Zhen Chen ^a, Ke-Wei Lei ^a,^*

PMCID: PMC2968433 PMID: 21582230

Abstract

The crystal structure of the title compound, C₁₈H₂₆N₂O₃, is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds. One of the methyl groups is disordered with occupancies of 0.51 (3):0.49 (3).

Related literature

For the properties of metallocrowns, see: Alexiou et al. (2002 ▶); Gaynor et al. (2002 ▶); Lah & Pecoraro (1989 ▶); Lehaire et al. (2002 ▶); Liu et al. (2001 ▶, 2008 ▶); Saalfrank et al. (2001 ▶).

Experimental

Crystal data

C₁₈H₂₆N₂O₃
M _r = 318.41
Monoclinic,
a = 16.193 (5) Å
b = 16.194 (5) Å
c = 6.856 (2) Å
β = 97.892 (4)°
V = 1780.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.43 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none T _min = 0.970, T _max = 0.983
8728 measured reflections
6453 independent reflections
3925 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.080
wR(F ²) = 0.211
S = 1.05
6453 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.60 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900556X/jh2073sup1.cif

e-65-0o575-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900556X/jh2073Isup2.hkl

e-65-0o575-Isup2.hkl^{(111KB, 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
N1—H1A⋯O2ⁱ	0.86	2.05	2.821 (4)	149
O1—H1B⋯O3	0.82	1.92	2.636 (4)	145
N2—H2A⋯O3ⁱⁱ	0.86	2.10	2.898 (4)	154

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This project was sponsored by the K. C. Wong Magna Fund of Ningbo University and Ningbo Municipal Natural Science Foundation (2008 A610051)

supplementary crystallographic information

Comment

Metallacrowns are important compounds. Because of their potentially unique properties (Alexiou et al., 2002; Gaynor et al., 2002; Lah & Pecoraro, 1989; Lehaire et al., 2002; Liu et al., 2001; Saalfrank et al., 2001), they have gained increasing attention over the past decade. These compounds can be readily assembled using a trianionic pentadentate ligand,N-acylsalicylhydrazide,having a trivalent octahedral metal ion. The size of the metallacrown can be controlled by modifying the close-contact interaction between the N-acyl residues of the ligands (Liu et al., 2008). We now report structure of a designed pentadentate ligand, N-4-isoPropylcyclohexyl-3-methyl-salicylhydrazide.

A view of the title structure is illustrated in Fig.1. Because of C1 splited into C1 and C1', It made the U_eq of neighbor atoms lower or larger than usual U_eq. The molecular conformation is characterized by N—H···O hydrogen bonds and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds(Fig.2).

Experimental

Trimethylaceto chloride (6.025 g, 50.0 mmol) was added to 50 ml chloroform solution of 4-isoPropylcyclohexyl acid with an external ice-water bath and triethylamine(5.200 g, 50.0 mmol). stirred for about 30 min slowly warmed to ambient temperature. To the above solution, 3-methyl-salicylhydrazide (7.636 g, 46.0 mmol)was added and stirred for 30 min. A white suspension began to appear after a while.the resulting white precipitate was filtered and rinsed with chloroform and diethyl ether. The title compound was recrystallized from methanol solution.