N-[4-(9-Chloro­quino[3,2-b]benzo[1,4]thia­zin-6-yl)but­yl]acetamidePart CXXXIII in the series of Azinyl sulfides.

Jeleń, M.; Suwińska, K.; Pluta, K.; Morak-Młodawska, B.

doi:10.1107/S1600536812045680

Volume 68
Part 12
Pages o3324-o3325
December 2012

Received 26 September 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.067
wR = 0.127
Data-to-parameter ratio = 12.4
Details

N-[4-(9-Chloroquino[3,2-b]benzo[1,4]thiazin-6-yl)butyl]acetamide¹

Malgorzata Jelen,^a Kinga Suwinska,^b,^c Krystian Pluta ^a ^* and Beata Morak-Mlodawska ^a

^aDepartment of Organic Chemistry, The Medical University of Silesia, ul. Jagiellonska 4, 41-200 Sosnowiec, Poland,^bInstitute of Physical Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland, and ^cFaculty of Biology and Environmental, Sciences, Cardinal Stefan Wyszynski University, ul. Wóycickiego 1/3, PL-01 938, Warszawa, Poland
Correspondence e-mail: pluta@sum.edu.pl

In the title molecule, C₂₁H₂₀ClN₃OS, the tetracyclic system is close to planar [r.m.s. deviation = 0.110 (4) Å]. The dihedral angle between the quinoline ring system and the benzene ring is 178.3 (1)° and the angle between two (S-C=C-N) halves of the thiazine ring is 173.4 (1)°. In the crystal, molecules are arranged via [pi] - [pi] interactions [centroid-centroid distances = 3.603 (2)-3.739 (2) Å] into slipped stacks extending along [010]. Intermolecular N-HO hydrogen bonds link the amide groups of neighbouring molecules along the stack, generating a C(4) motif. The title compound shows promising antiproliferative and anticancer activity.

Related literature

For recent literature on biological activity of phenothiazines, see: Aaron et al. (2009); Pluta et al. (2011). For the synthesis and biological activity of 6-substituted quinobenzothiazines, see: Jelen & Pluta (2009); Pluta et al. (2012). For the folded structures of similar tetracyclic systems, see: Jelen et al. (2012); Luck et al. (2003); Yoshida et al. (1994). For crystal structures of phenothiazines, see: Chu (1988). For information on azaphenothiazines, and their nomenclature and synthesis, see: Pluta et al. (2009).

Experimental

Crystal data

C₂₁H₂₀ClN₃OS
M_r = 397.92
Monoclinic, P 2₁ /c
a = 12.7800 (4) Å
b = 4.9530 (11) Å
c = 28.781 (2) Å
= 97.726 (5)°
V = 1805.3 (4) Å³
Z = 4
Mo K radiation
= 0.35 mm^-1
T = 100 K
0.60 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer upgraded with an APEXII detector
17434 measured reflections
3032 independent reflections
1987 reflections with I > 2(I)
R_int = 0.121

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.127
S = 1.10
3032 reflections
245 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N18-H18O21ⁱ	0.88	1.97	2.819 (4)	163
Symmetry code: (i) x, y+1, z.

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2524 ).

Acknowledgements

The work was supported by the National Centre of Science (grant No. N405 101739).

References

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