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Volume 68 
Part 12 
Page o3369  
December 2012  

Received 16 October 2012
Accepted 7 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 16.8
Details
Open access

1-(10H-phenothiazin-10-yl)ethanone

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

In the title compound, C14H11NOS, the phenothiazine unit has a butterfly conformation and the central six-membered ring has a boat form. The fold angle between the benzene rings is 46.39 (7)°, which is larger than found in similar compounds, probably as a result of steric repulsion between the phenothiazine fragment and the acetyl group.

Related literature

For the structures of related N-alkylphenothiazine derivatives, see: Chu & Van der Helm (1974[Chu, S. S. C. & Van der Helm, D. (1974). Acta Cryst. B30, 2489-2490.], 1975[Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179-1183.]) and of related N-acetylphenothiazine derivatives, see: Meester & Chu (1986[Meester, P. & Chu, S. S. C. (1986). J. Heterocycl. Chem. 23, 1249-1252.]); Wang et al. (2009[Wang, Q., Yang, L., Xu, Z. & Sun, Y. (2009). Acta Cryst. E65, o1978.]); Siddegowda et al. (2011[Siddegowda, M. S., Jasinski, J. P., Golen, J. A. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1702.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11NOS

  • Mr = 241.31

  • Monoclinic, C 2/c

  • a = 21.435 (6) Å

  • b = 8.897 (3) Å

  • c = 12.738 (4) Å

  • [beta] = 111.753 (3)°

  • V = 2256.2 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 93 K

  • 0.17 × 0.10 × 0.10 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.969, Tmax = 0.974

  • 9030 measured reflections

  • 2584 independent reflections

  • 2337 reflections with F2 > 2[sigma](F2)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.03

  • 2584 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2074 ).


Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

References

Chu, S. S. C. & Van der Helm, D. (1974). Acta Cryst. B30, 2489-2490.  [CrossRef] [details] [ISI]
Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179-1183.  [CrossRef] [details] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Meester, P. & Chu, S. S. C. (1986). J. Heterocycl. Chem. 23, 1249-1252.
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siddegowda, M. S., Jasinski, J. P., Golen, J. A. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1702.  [CSD] [CrossRef] [details]
Wang, Q., Yang, L., Xu, Z. & Sun, Y. (2009). Acta Cryst. E65, o1978.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3369  [ doi:10.1107/S1600536812045904 ]

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