7-[(3-Chloro-6-methyl-6,11-dihydro­dibenzo[c,f][1,2]thia­zepin-11-yl)amino]­hepta­noic acid S,S-dioxide hydro­chloride

Mishnev, A.; Zvirgzdins, A.; Actins, A.; Delina, M.

doi:10.1107/S1600536812042432

Volume 68
Part 11
Page o3136
November 2012

Received 31 August 2012
Accepted 10 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 190 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.100
Data-to-parameter ratio = 18.3
Details

7-[(3-Chloro-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid S,S-dioxide hydrochloride

Anatoly Mishnev,^a Alvis Zvirgzdins,^b ^* Andris Actins ^b and Mara Delina ^b

^aLatvian Institute of Organic Synthesis, Aizkraukles Street 21, Riga, LV-1006, Latvia, and ^bUniversity of Latvia, Department of Chemistry, Kr. Valdemara Street 48, Riga, LV-1013, Latvia
Correspondence e-mail: alvis.zvirgzdins@lais.lv

In the title compound, C₂₁H₂₆ClN₂O₄S^.Cl, also known as tianeptine hydrochloride, the seven-membered ring adopts a boat conformation. The dihedral angle between the mean planes of the benzene rings is 44.44 (7)°. There is an intramolecular hydrogen bond formed via S= OH-N. In the crystal, molecules are connected via pairs of N-H.·O, N-HCl and O-HCl hydrogen bonds, forming inversion dimers, which are consolidated by C-HO interactions. The dimers are linked by C-HO and C-HCl interactions, forming a two-dimensional network lying parallel to (011).

Related literature

For general information about tianeptine and its preparation, see: Guzman et al. (2010). For related structures, see: Orola et al. (2012).

Experimental

Crystal data

C₂₁H₂₆ClN₂O₄S⁺·Cl^-
M_r = 473.40
Triclinic, $[P \overline 1]$
a = 9.5439 (2) Å
b = 10.0910 (2) Å
c = 13.1802 (3) Å
= 104.000 (1)°
= 101.538 (1)°
= 105.018 (1)°
V = 1139.04 (4) Å³
Z = 2
Mo K radiation
= 0.41 mm^-1
T = 190 K
0.24 × 0.20 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
7552 measured reflections
4985 independent reflections
4015 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.100
S = 1.03
4985 reflections
273 parameters
H-atom parameters constrained
_max = 0.76 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H3ACl2ⁱ	0.90	2.31	3.154 (2)	157
N2-H3BO3ⁱⁱ	0.90	2.32	2.821 (2)	115
C16-H11BO3ⁱⁱ	0.97	2.56	3.201 (2)	124
O4-H6Cl2ⁱⁱⁱ	0.82	2.22	3.043 (2)	176
C4-H3Cl2^iv	0.93	2.82	3.651 (2)	150
C18-H6AO4^v	0.97	2.56	3.467 (2)	157
C7-H7Cl2	0.98	2.59	3.534 (2)	162
N2-H3BO2	0.90	2.02	2.802 (2)	144
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+1, -z+1; (iii) x, y, z+1; (iv) -x+1, -y+1, -z; (v) -x+1, -y+1, -z+1.

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2586 ).

Acknowledgements

This work was supported by the European Regional Development Fund (No. 2011/0014/2DP/2.1.1.1.0/10/APIA/VIAA/092).

References

Guzman, H., Popov, A., Rammeloo, T. J. L., Remenar, J., Saoud, J. B. & Tawa, M. (2010). US Patent No. 20,100,112,051 A1 20100506.
Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Orola, L., Veidis, M. V., Sarcevica, I., Actins, A., Belyakov, S. & Platonenko, A. (2012). Int. J. Pharm. 432, 50-56.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds