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Volume 70 
Part 1 
Page o18  
January 2014  

Received 6 November 2013
Accepted 30 November 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.084
Data-to-parameter ratio = 13.4
Details
Open access

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

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China,bSchool of Chemistry and Chemical Engineering, Taian University, Taian 271021, People's Republic of China, and cSchool of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, People's Republic of China
Correspondence e-mail: duanwenzeng@163.com

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[Cram, D. J. (1959). Rec. Chem. Prog. 20, 71-93.]); Liebman & Greenberg (1976[Liebman, J. F. & Greenberg, A. (1976). Chem. Rev. 76, 311-365.]); Dyson et al. (1998[Dyson, P. J., Johnson, B. F. G. & Martin, C. M. (1998). Coord. Chem. Rev. 175, 59-89.]). For its synthesis and applications in catalysis, see: Hou et al. (2000[Hou, X. L., Wu, X. W., Dai, L. X., Cao, B. X. & Sun, J. (2000). Chem. Commun. pp. 1195-1196.]); Duan et al. (2008[Duan, W. Z., Ma, Y. D., Xia, H. Q., Liu, X. Y., Ma, Q. S. & Sun, J. S. (2008). J. Org. Chem. 73, 4330-4333.], 2012[Duan, W. Z., Ma, Y. D., Qu, B., Zhao, L., Chen, J. Q. & Song, C. (2012). Tetrahedron Asymmetry, 23, 1369-1375.]). For a related structure, see: Ma et al. (2012[Ma, K., Duan, W., He, F. & Ma, Y. (2012). Acta Cryst. E68, o1380.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19NO3S

  • Mr = 317.39

  • Orthorhombic, P 21 21 21

  • a = 8.017 (7) Å

  • b = 11.734 (9) Å

  • c = 16.131 (13) Å

  • V = 1517 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.978

  • 7769 measured reflections

  • 2676 independent reflections

  • 2266 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.084

  • S = 1.04

  • 2676 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1122 Friedel pairs

  • Absolute structure parameter: 0.02 (9)

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
Symmetry codes: (i) [-x+{\script{5\over 2}}, -y+1, z-{\script{1\over 2}}]; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5436 ).


Acknowledgements

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

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cram, D. J. (1959). Rec. Chem. Prog. 20, 71-93.  [ChemPort]
Duan, W. Z., Ma, Y. D., Qu, B., Zhao, L., Chen, J. Q. & Song, C. (2012). Tetrahedron Asymmetry, 23, 1369-1375.  [Web of Science] [CrossRef] [ChemPort]
Duan, W. Z., Ma, Y. D., Xia, H. Q., Liu, X. Y., Ma, Q. S. & Sun, J. S. (2008). J. Org. Chem. 73, 4330-4333.  [CSD] [CrossRef] [PubMed] [ChemPort]
Dyson, P. J., Johnson, B. F. G. & Martin, C. M. (1998). Coord. Chem. Rev. 175, 59-89.  [Web of Science] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Hou, X. L., Wu, X. W., Dai, L. X., Cao, B. X. & Sun, J. (2000). Chem. Commun. pp. 1195-1196.  [CSD] [CrossRef]
Liebman, J. F. & Greenberg, A. (1976). Chem. Rev. 76, 311-365.  [CrossRef] [ChemPort] [Web of Science]
Ma, K., Duan, W., He, F. & Ma, Y. (2012). Acta Cryst. E68, o1380.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o18  [ doi:10.1107/S1600536813032595 ]

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