1-(10H-Phenothia­zin-2-yl)ethanone

Jasinski, J.P.; Pek, A.E.; Nayak, P.S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811001851

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 20.9
Details

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

Jerry P. Jasinski,^a ^* Albert E. Pek,^a Prakash S. Nayak,^b B. Narayana ^b and H. S. Yathirajan ^c

^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-HO 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); Wermuth (2003); Wang et al. (2008); Lam et al. (2001); Kojilo et al. (2001). For related structures, see: Bell et al. (1968); McDowell (1969, 1970, 1975, 1976, 1978, 1980); Chu & Van der Helm (1974, 1975, 1977)); Phelps & Cordes (1974, 1975); Harrison et al. (2007); Wang et al. (2009). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₄H₁₁NOS
M_r = 241.30
Monoclinic, P 2₁ /c
a = 14.3445 (18) Å
b = 5.5425 (7) Å
c = 15.694 (2) Å
= 114.494 (2)°
V = 1135.4 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.868, T_max = 0.974
8194 measured reflections
3331 independent reflections
2828 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(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
_max = 0.49 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C7-C12 ring.

D-HA	D-H	HA	DA	D-HA
N1-H15O1ⁱ	0.829 (18)	2.198 (18)	3.0042 (15)	164.3 (17)
C9-H14Cg3ⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); 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.
Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179-1183.
Chu, S. S. C. & van der Helm, D. (1977). Acta Cryst. B33, 873-876.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
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organic compounds