(E)-N-[2-(3,5-Di-tert-butyl-2-hydroxy­benzyl­ideneamino)cyclo­hexyl]-4-methyl­benzene­sulfonamide

Jincai Wu; Lei Wang; Xiaobo Pan; Lihui Yao

doi:10.1107/S1600536808043870

. 2009 Jan 8;65(Pt 2):o255. doi: 10.1107/S1600536808043870

(E)-N-[2-(3,5-Di-tert-butyl-2-hydroxybenzylideneamino)cyclohexyl]-4-methylbenzenesulfonamide

Jincai Wu ^a,^*, Lei Wang ^a, Xiaobo Pan ^a, Lihui Yao ^a

PMCID: PMC2968280 PMID: 21581871

Abstract

In the crystal structure of the title compound, C₂₈H₄₀N₂O₃S, there are two molecules per asymmetric unit; in each of these molecules, the cyclohexyl rings adopt chair conformations. The dihedral angles between the benzene rings are 16.89 (9) and 34.11 (9)°. Each molecule contains an intramolecular O—H⋯N hydrogen bond, and intermolecular N—H⋯O hydrogen bonds are also present. In both molecules, the methyl groups of one tert-butyl group are disordered over two positions; the site-occupancy factors in both cases are ca 0.6 and 0.4.

Related literature

For the polymerization of cyclic esters, see: Endo et al. (1987 ▶); Wu et al. (2006 ▶). For synthetic details, see: Balsells et al. (1998 ▶).

Experimental

Crystal data

C₂₈H₄₀N₂O₃S
M _r = 484.68
Monoclinic,
a = 10.3873 (10) Å
b = 25.773 (2) Å
c = 10.4127 (10) Å
β = 97.269 (2)°
V = 2765.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 298 (2) K
0.35 × 0.30 × 0.21 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (MULscanABS in SADABS; Sheldrick, 2002 ▶) T _min = 0.950, T _max = 0.970
15079 measured reflections
9696 independent reflections
7043 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.119
S = 0.97
9696 reflections
689 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 4173 Friedel pairs
Flack parameter: −0.04 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2003 ▶) and local programs.

Supplementary Material

Crystal structure: contains datablocks I, gobal. DOI: 10.1107/S1600536808043870/wn2301sup1.cif

e-65-0o255-sup1.cif^{(40.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043870/wn2301Isup2.hkl

e-65-0o255-Isup2.hkl^{(474.2KB, 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
O1—H1⋯N1	0.82	1.89	2.621 (3)	149
O4—H4A⋯N3	0.82	1.88	2.619 (3)	149
N2—H2B⋯O5ⁱ	0.86	2.36	2.987 (3)	130
N4—H4B⋯O2ⁱⁱ	0.86	2.30	2.950 (3)	133

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

Acknowledgments

We are grateful for the financial support of the National Science Foundation of China (grant No. 20601011) and the Science Foundation of Gansu Province of China (grant No. 0803RJZA103).

supplementary crystallographic information

Comment

Recently, significant advances have been made in the polymerization of cyclic esters, such as poly-ε-caprolactone (Endo et al., 1987), polylactide (Wu et al., 2006) A particularly convenient method for the synthesis of polylactides is the ring-opening polymerization (ROP) of lactides. Due to the advantages of well-controlled molecular weight and low polydispersity (PDI), many metal complexes have been used. In the present study, we report a structure which is a potential ligand for the investigation of ROP of lactides.

As shown in Fig. 1, the asymmetric unit contains two molecules. In each of these molecules the cyclohexyl rings adopt chair conformations. The dihedral angles between the benzene rings are 16.89 (9)° and 34.11 (9)°. The bond lengths and angles are within normal ranges. Each molecule contains an intramolecular O—H···N hydrogen bond and intermolecular N—H···O hydrogen bonds are also present (Table 1 and Fig. 2). A short contact O2···.C43, with a distance of 3.011 (4) Å, involves the interaction of S=O and C=N.

Experimental

The title compound was prepared as described in the literature (Balsells et al., 1998). A fine crystal was obtained from an acetonitrile solution.