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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 [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.100
Data-to-parameter ratio = 18.3
Details
Open access

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

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= O...H-N. In the crystal, molecules are connected via pairs of N-H.·O, N-H...Cl and O-H...Cl hydrogen bonds, forming inversion dimers, which are consolidated by C-H...O interactions. The dimers are linked by C-H...O and C-H...Cl 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[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.]). For related structures, see: Orola et al. (2012[Orola, L., Veidis, M. V., Sarcevica, I., Actins, A., Belyakov, S. & Platonenko, A. (2012). Int. J. Pharm. 432, 50-56.]).

[Scheme 1]

Experimental

Crystal data
  • C21H26ClN2O4S+·Cl-

  • Mr = 473.40

  • Triclinic, [P \overline 1]

  • a = 9.5439 (2) Å

  • b = 10.0910 (2) Å

  • c = 13.1802 (3) Å

  • [alpha] = 104.000 (1)°

  • [beta] = 101.538 (1)°

  • [gamma] = 105.018 (1)°

  • V = 1139.04 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.100

  • S = 1.03

  • 4985 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.76 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H3A...Cl2i 0.90 2.31 3.154 (2) 157
N2-H3B...O3ii 0.90 2.32 2.821 (2) 115
C16-H11B...O3ii 0.97 2.56 3.201 (2) 124
O4-H6...Cl2iii 0.82 2.22 3.043 (2) 176
C4-H3...Cl2iv 0.93 2.82 3.651 (2) 150
C18-H6A...O4v 0.97 2.56 3.467 (2) 157
C7-H7...Cl2 0.98 2.59 3.534 (2) 162
N2-H3B...O2 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[Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.]); cell refinement: HKL DENZO (Otwinowski & Minor, 1997[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.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[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.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
Orola, L., Veidis, M. V., Sarcevica, I., Actins, A., Belyakov, S. & Platonenko, A. (2012). Int. J. Pharm. 432, 50-56.  [ISI] [CrossRef] [ChemPort] [PubMed]
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.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3136  [ doi:10.1107/S1600536812042432 ]

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