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Volume 67 
Part 2 
Pages o430-o431  
February 2011  

Received 5 January 2011
Accepted 12 January 2011
Online 22 January 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 20.9
Details
Open access

1-(10H-Phenothiazin-2-yl)ethanone

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C14H11NOS, the thiazine ring adopts a slightly distorted boat conformation. The dihedral angle between the mean planes of the two benzene rings is 20.2 (9)°. An intermolecular N-H...O hydrogen bond and a weak C-H...[pi] interaction occur in the crystal, creating a two-dimensional network parallel to the bc plane.

Related literature

For applications of phenothiazines in drugs and medicine, see: Miller et al. (1999[Miller, M. T., Gantzel, P. K. & Karpishin, T. B. (1999). J. Am. Chem. Soc. 121, 4292-4293.]); Wermuth (2003[Wermuth, C. G. (2003). The Practice of Medicinal Chemistry, 2nd ed. London: Acdemic Press.]); Wang et al. (2008[Wang, J., Dong, M., Liang, J., Chang, Z., Feng, S., Wang, H. & Ding, N. (2008). Chin. J. Lab. Diagn. 12, 381-382.]); Lam et al. (2001[Lam, M., Oleinick, N. L. & Nieminen, A. L. (2001). J. Biol. Chem. 276, 47379-47386.]); Kojilo et al. (2001[Kojilo, A., Karpinska, J., Kuzmicka, L., Misiuk, W., Puzanowska-Tarasiewicz, H. & Tarasiewicz, M. (2001). J. Trace Microprobe Technol. 19, 45-70.]). For related structures, see: Bell et al. (1968[Bell, J. D., Blount, J. F., Briscoe, O. V. & Freeman, H. C. (1968). Chem. Commun. (London), pp. 1656-1657.]); McDowell (1969[McDowell, J. J. H. (1969). Acta Cryst. B25, 2175-2181.], 1970[McDowell, J. J. H. (1970). Acta Cryst. B26, 954-964.], 1975[McDowell, J. J. H. (1975). Acta Cryst. B31, 2256-2264.], 1976[McDowell, J. J. H. (1976). Acta Cryst. B32, 5-10.], 1978[McDowell, J. J. H. (1978). Acta Cryst. B34, 686-689.], 1980[McDowell, J. J. H. (1980). Acta Cryst. B36, 2178-2181.]); 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.], 1977)[Chu, S. S. C. & van der Helm, D. (1977). Acta Cryst. B33, 873-876.]); Phelps & Cordes (1974[Phelps, D. W. & Cordes, A. W. (1974). Acta Cryst. B30, 2812-2816.], 1975[Phelps, D. W. & Cordes, A. W. (1975). Acta Cryst. B31, 2542-2544.]); Harrison et al. (2007[Harrison, W. T. A., Ashok, M. A., Yathirajan, H. S. & Narayana Achar, B. (2007). Acta Cryst. E63, o3322.]); Wang et al. (2009[Wang, Q., Yang, L., Xu, Z. & Sun, Y. (2009). Acta Cryst. E65, o1978.]). 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
  • C14H11NOS

  • Mr = 241.30

  • Monoclinic, P 21 /c

  • a = 14.3445 (18) Å

  • b = 5.5425 (7) Å

  • c = 15.694 (2) Å

  • [beta] = 114.494 (2)°

  • V = 1135.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 100 K

  • 0.55 × 0.55 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA]) Tmin = 0.868, Tmax = 0.974

  • 8194 measured reflections

  • 3331 independent reflections

  • 2828 reflections with I > 2[sigma](I)

  • Rint = 0.025

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

  • wR(F2) = 0.108

  • S = 1.04

  • 3331 reflections

  • 159 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
N1-H15...O1i 0.829 (18) 2.198 (18) 3.0042 (15) 164.3 (17)
C9-H14...Cg3ii 0.93 2.64 3.306 (7) 130
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2662 ).


Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU. BN thanks Mangalore University for the research facilities and the UGC for financial assistance through a SAP chemical grant. HSY thanks the University of Mysore for sabbatical leave.

References

Bell, J. D., Blount, J. F., Briscoe, O. V. & Freeman, H. C. (1968). Chem. Commun. (London), pp. 1656-1657.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA
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]
Chu, S. S. C. & van der Helm, D. (1977). Acta Cryst. B33, 873-876.  [CrossRef] [details] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Harrison, W. T. A., Ashok, M. A., Yathirajan, H. S. & Narayana Achar, B. (2007). Acta Cryst. E63, o3322.  [CrossRef] [details]
Kojilo, A., Karpinska, J., Kuzmicka, L., Misiuk, W., Puzanowska-Tarasiewicz, H. & Tarasiewicz, M. (2001). J. Trace Microprobe Technol. 19, 45-70.
Lam, M., Oleinick, N. L. & Nieminen, A. L. (2001). J. Biol. Chem. 276, 47379-47386.  [CrossRef] [PubMed] [ChemPort]
McDowell, J. J. H. (1969). Acta Cryst. B25, 2175-2181.  [CrossRef] [ChemPort] [details] [ISI]
McDowell, J. J. H. (1970). Acta Cryst. B26, 954-964.  [CrossRef] [ChemPort] [details] [ISI]
McDowell, J. J. H. (1975). Acta Cryst. B31, 2256-2264.  [CrossRef] [details] [ISI]
McDowell, J. J. H. (1976). Acta Cryst. B32, 5-10.  [CrossRef] [details] [ISI]
McDowell, J. J. H. (1978). Acta Cryst. B34, 686-689.  [CrossRef] [details] [ISI]
McDowell, J. J. H. (1980). Acta Cryst. B36, 2178-2181.  [CrossRef] [details] [ISI]
Miller, M. T., Gantzel, P. K. & Karpishin, T. B. (1999). J. Am. Chem. Soc. 121, 4292-4293.  [ISI] [CSD] [CrossRef] [ChemPort]
Phelps, D. W. & Cordes, A. W. (1974). Acta Cryst. B30, 2812-2816.  [CrossRef] [details] [ISI]
Phelps, D. W. & Cordes, A. W. (1975). Acta Cryst. B31, 2542-2544.  [CrossRef] [details] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, J., Dong, M., Liang, J., Chang, Z., Feng, S., Wang, H. & Ding, N. (2008). Chin. J. Lab. Diagn. 12, 381-382.
Wang, Q., Yang, L., Xu, Z. & Sun, Y. (2009). Acta Cryst. E65, o1978.  [CSD] [CrossRef] [details]
Wermuth, C. G. (2003). The Practice of Medicinal Chemistry, 2nd ed. London: Acdemic Press.


Acta Cryst (2011). E67, o430-o431   [ doi:10.1107/S1600536811001851 ]

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