4-Amino-12-methyl­sulfon­yloxy-[2.2]para­cyclo­phane

Xiangchao Meng; Wenzeng Duan; Yinfeng Han

doi:10.1107/S1600536813032595

. 2013 Dec 7;70(Pt 1):o18. doi: 10.1107/S1600536813032595

4-Amino-12-methylsulfonyloxy-[2.2]paracyclophane

Xiangchao Meng ^a, Wenzeng Duan ^b,^c,^*, Yinfeng Han ^b

PMCID: PMC3914068 PMID: 24526969

Abstract

The title compound, C₁₇H₁₉NO₃S, was synthesized from 4-benzhydrylideneamino-12-hydroxy-[2.2]paracyclophane and methanesulfonyl chloride. In the molecule, the distance between the centroids of two aromatic rings is 2.960 (5) Å. In the crystal, weak N—H⋯O and C—H⋯O hydrogen bonds link the molecules into layers parallel to the ac plane.

Related literature

For background to [2.2]paracyclophane, see: Cram et al. (1959 ▶); Liebman & Greenberg (1976 ▶); Dyson et al. (1998 ▶). For its synthesis and applications in catalysis, see: Hou et al. (2000 ▶); Duan et al. (2008 ▶, 2012 ▶). For a related structure, see: Ma et al. (2012 ▶). graphic file with name e-70-00o18-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₉NO₃S
M _r = 317.39
Orthorhombic,
a = 8.017 (7) Å
b = 11.734 (9) Å
c = 16.131 (13) Å
V = 1517 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 273 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.971, T _max = 0.978
7769 measured reflections
2676 independent reflections
2266 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.084
S = 1.04
2676 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 1122 Friedel pairs
Absolute structure parameter: 0.02 (9)

Data collection: SMART (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 datablock(s) I, global. DOI: 10.1107/S1600536813032595/cv5436sup1.cif

e-70-00o18-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032595/cv5436Isup2.hkl

e-70-00o18-Isup2.hkl^{(131.4KB, hkl)}

Additional supporting information: 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—H1B⋯O2ⁱ	0.86	2.43	3.262 (3)	163
C10—H10B⋯O1ⁱⁱ	0.97	2.52	3.390 (4)	149

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

Acknowledgments

Financial support from Shandong Province Natural Science Foundation (ZR2012BL08) is gratefully acknowledged.

supplementary crystallographic information

1. Comment

Since the first synthesis of [2.2]paracyclophane (Cram, 1959), its structure atrracted considerable interest (Liebman et al., 1976; Dyson et al., 1998). [2.2]Paracyclophane needs only one substituent to become planar chiral, so, there has been notable progress with regard to the synthesis of new derivatives and their applications in asymmetric catalysis(Hou et al., 2000; Duan et al., 2008).

In the title compound (Fig. 1), all bond lengths and angles are normal and in agreement with those observed in the related structure (Ma et al., 2012). In the molecule, the distance between the centroids of two aromatic rings is 2.960 (5) Å. The crystal packing exhibits weak intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), which link the molecules into layers parallel to the ac plane.

2. Experimental

The title compound was prepared by the method reported by Duan et al. (2012). The crystals were obtained by recrystallization from hexane and ethyl acetate.