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Volume 69 
Part 7 
Page o1165  
July 2013  

Received 17 June 2013
Accepted 22 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.138
Data-to-parameter ratio = 16.6
Details
Open access

8-Phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18-heptaene

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
Correspondence e-mail: eesans@yahoo.com

In the title compound, C24H18S, the dihedral angles between the phenyl ring and the two benzene rings of the anthracene moiety are 51.92 (9) and 68.24 (9)°, whereas the dihedral angle between the two anthracene benzene rings is 120.13 (9)°. The three non-aromatic six-membered rings are in boat conformations, while the five-membered ring has an envelope conformation on the S atom. In the crystal, there are three C-H...[pi] interactions, which facilitate the packing of the molecules.

Related literature

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010[Khalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353-1360.]); Cox et al. (2013[Cox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640-643.]). For the synthesis of related compounds, see: Ciganek (1980[Ciganek, E. (1980). J. Org. Chem. 45, 1497-1505.]); Vetter (1998[Vetter, S. (1998). Synth. Commun. 28, 3219-3223.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18S

  • Mr = 338.44

  • Orthorhombic, P b c a

  • a = 18.8842 (11) Å

  • b = 9.5339 (4) Å

  • c = 19.1140 (9) Å

  • V = 3441.3 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.945, Tmax = 0.963

  • 22858 measured reflections

  • 3757 independent reflections

  • 2765 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.138

  • S = 1.02

  • 3757 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19-C2 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg1i 0.93 2.80 3.516 (2) 135
C5-H5...Cg1ii 0.93 2.76 3.5844 (19) 149
C15-H15B...Cg2iii 0.97 2.98 3.845 (2) 149
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y-1, z+{\script{3\over 2}}]; (ii) -x+1, -y+2, -z+2; (iii) [x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2554 ).


Acknowledgements

EMM is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of a Senior Research Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the single-crystal X-ray diffraction measurements.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ciganek, E. (1980). J. Org. Chem. 45, 1497-1505.  [CrossRef] [ChemPort]
Cox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640-643.  [CrossRef] [ChemPort] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Khalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353-1360.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vetter, S. (1998). Synth. Commun. 28, 3219-3223.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1165  [ doi:10.1107/S1600536813017285 ]

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