(Z)-3-(2-Meth­oxy­benz­yl)-1,5-benzo­thia­zepin-4(5H)-one

Selvakumar, R.; Bakthadoss, M.; Lakshmanan, D.; Murugavel, S.

doi:10.1107/S160053681202661X

Volume 68
Part 7
Page o2126
July 2012

Received 10 June 2012
Accepted 12 June 2012
Online 16 June 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.146
Data-to-parameter ratio = 21.7
Details

(Z)-3-(2-Methoxybenzyl)-1,5-benzothiazepin-4(5H)-one

R. Selvakumar,^a M. Bakthadoss,^a ⁺ D. Lakshmanan ^b and S. Murugavel ^c ^*

^aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,^bDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, and ^cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C₁₇H₁₅NO₂S, the seven-membered thiazepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean planes of the benzothiazepin ring system and the attached benzene ring is 47.7 (1)°. In the crystal, pairs of N-HO hydrogen bonds link inversion-related molecules into dimers, generating R₂²(8) ring motifs. These dimers are further connected into a chain along the a axis by C-HO hydrogen bonds, resulting in R₂²(14) ring motifs. The crystal packing also features C-H [pi] interactions.

Related literature

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000). For related structures, see: Sridevi et al. (2011); Sabari et al. 2011). For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₁₅NO₂S
M_r = 297.36
Triclinic, $[P \overline 1]$
a = 8.6665 (5) Å
b = 9.7612 (4) Å
c = 10.1328 (5) Å
= 108.181 (3)°
= 101.561 (2)°
= 103.217 (3)°
V = 757.83 (7) Å³
Z = 2
Mo K radiation
= 0.22 mm^-1
T = 293 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.951, T_max = 0.968
16048 measured reflections
4137 independent reflections
2797 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.146
S = 1.01
4137 reflections
191 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.00	2.8545 (17)	171
C5-H5O1ⁱⁱ	0.93	2.39	3.308 (2)	171
C3-H3Cgⁱⁱⁱ	0.93	2.69	3.432 (2)	138
C17-H17CCg^iv	0.96	2.90	3.664 (2)	137
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+2, -z+1; (iv) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6847 ).

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sabari, V., Jagadeesan, G., Selvakumar, R., Bakthadoss, M. & Aravindhan, S. (2011). Acta Cryst. E67, o3061.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sridevi, D., Bhaskaran, S., Usha, G., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o243.
Tomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479-493.

organic compounds