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Volume 68 
Part 11 
Pages o3133-o3134  
November 2012  

Received 4 October 2012
Accepted 9 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.086
Data-to-parameter ratio = 13.1
Details
Open access

Dibenzo[b,f][1,4]thiazepin-11-yl-diethyl-amine

aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy,bICS, Université de Strasbourg, Strasbourg, France, and cDipartimento Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

In the title compound, C17H18N2S, the thiazepine ring adopts a boat conformation and the dihedral angle between the benzene rings is 75.92 (5)°, resulting in a butterfly-like conformation. In the crystal, molecules are connected via weak Caromatic-H...N contacts involving the imine N atom as acceptor and through a quite short C-H...[pi] interaction. The resulting molecular chains propagate along the c-axis direction.

Related literature

For `privileged structures', that is `structures able to provide high affinity ligands for more than one type of receptor', see: Evans et al. (1988[Evans, B. E., Rittle, K. E., Bock, M. G., DiPardo, R. M., Freidinger, R. M., Whittle, W. L., Lundell, G. F., Veber, D. F., Anderson, P. S., Chang, R. S. L., Lotti, V. J., Cerino, D. J., Chen, T. B., Kling, P. J., Kunkel, K. A., Springer, J. P. & Hirshfield, J. (1988). J. Med. Chem. 31, 2235-2246.]); Patchett & Nargund (2000[Patchett, A. A. & Nargund, R. P. (2000). Annu. Rep. Med. Chem. 35, 289-298.]); Fedi et al. (2008[Fedi, V., Guidi, A. & Altamura, M. (2008). Mini Rev. Med. Chem. 8, 1464-1484.]). For the clinical use of dibenzothiazepine derivatives, see: Ganesh et al. (2011[Ganesh, D. M., Yogesh, M. K., Ashok, K., Dharmendra, S., Kisan, M. K. & Suresh, B. M. (2011). Indian J. Chem. 50B, 1196-, 1201.]); Pettersson et al. (2009[Pettersson, H., Bulow, A., Ek, F., Jensen, J., Ottesen, L. K., Fejzic, A., Ma, J.-N., Del Tredici, A. L., Currier, E. A., Gardell, L. R., Tabatabaei, A., Craig, D., McFarland, K., Ott, T. R., Piu, F., Burstein, E. S. & Olsson, R. (2009). J. Med. Chem. 52, 1975-1982.]); Riedel et al. (2007[Riedel, M., Mueller, N., Strassnig, M., Spellman, I., Severus, E. & Moeller, H.-J. (2007). Neuropsyc. Dis. Treat. 3, 219-235.]); Warawa et al. (2001[Warawa, E. J., Migler, B. M., Ohnmacht, C. J., Needles, A. L., Gatos, G. C., Mclaren, F. M., Nelson, C. L. & Kirkland, K. M. (2001). J. Med. Chem. 44, 372-389.]). For structure-property relationships in (6,7,6)-tricyclic ring systems, see: Ravikumar & Sridhar (2005[Ravikumar, K. & Sridhar, B. (2005). Acta Cryst. E61, o3245-o3248.]); Altamura et al. (2008[Altamura, M., Dapporto, P., Guidi, A., Harmat, N., Jerry, L., Libralesso, E., Paoli, P. & Rossi, P. (2008). New J. Chem. 32, 1617-1627.], 2009[Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.], 2011[Altamura, M., Guidi, A., Jerry, L., Paoli, P. & Rossi, P. (2011). CrystEngComm, 13, 2310-2317.]). For geometrical data and descriptors, see: Duax et al. (1976[Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, edited by E. L. Eliel and N. Allinger. New York: John Wiley & Sons.]); Bertolasi et al. (1982[Bertolasi, V., Ferretti, V., Gilli, G. & Borea, P. A. (1982). Cryst. Struct. Commun. 11, 1481-1486.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N2S

  • Mr = 282.40

  • Monoclinic, P 21 /c

  • a = 12.0137 (2) Å

  • b = 8.2257 (1) Å

  • c = 15.0513 (2) Å

  • [beta] = 102.952 (1)°

  • V = 1449.54 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.89 mm-1

  • T = 150 K

  • 0.20 × 0.18 × 0.03 mm

Data collection
  • Oxford Diffraction XcaliburPX diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.722, Tmax = 0.945

  • 6173 measured reflections

  • 2364 independent reflections

  • 1837 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.086

  • S = 1.05

  • 2364 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8-C12 ring.

D-H...A D-H H...A D...A D-H...A
C5-H5...N1i 0.95 2.70 3.576 (2) 154
C4-H4...Cgi 0.95 2.81 3.5759 (18) 139
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SIR92 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2296 ).


Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze) where the data collection was performed.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altamura, M., Dapporto, P., Guidi, A., Harmat, N., Jerry, L., Libralesso, E., Paoli, P. & Rossi, P. (2008). New J. Chem. 32, 1617-1627.  [ISI] [CSD] [CrossRef] [ChemPort]
Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219-2231.  [ISI] [CSD] [CrossRef] [ChemPort]
Altamura, M., Guidi, A., Jerry, L., Paoli, P. & Rossi, P. (2011). CrystEngComm, 13, 2310-2317.  [ISI] [CSD] [CrossRef] [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bertolasi, V., Ferretti, V., Gilli, G. & Borea, P. A. (1982). Cryst. Struct. Commun. 11, 1481-1486.  [ChemPort]
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, edited by E. L. Eliel and N. Allinger. New York: John Wiley & Sons.
Evans, B. E., Rittle, K. E., Bock, M. G., DiPardo, R. M., Freidinger, R. M., Whittle, W. L., Lundell, G. F., Veber, D. F., Anderson, P. S., Chang, R. S. L., Lotti, V. J., Cerino, D. J., Chen, T. B., Kling, P. J., Kunkel, K. A., Springer, J. P. & Hirshfield, J. (1988). J. Med. Chem. 31, 2235-2246.  [CrossRef] [ChemPort] [PubMed] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fedi, V., Guidi, A. & Altamura, M. (2008). Mini Rev. Med. Chem. 8, 1464-1484.  [CrossRef] [PubMed] [ChemPort]
Ganesh, D. M., Yogesh, M. K., Ashok, K., Dharmendra, S., Kisan, M. K. & Suresh, B. M. (2011). Indian J. Chem. 50B, 1196-, 1201.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Patchett, A. A. & Nargund, R. P. (2000). Annu. Rep. Med. Chem. 35, 289-298.  [CrossRef] [ChemPort]
Pettersson, H., Bulow, A., Ek, F., Jensen, J., Ottesen, L. K., Fejzic, A., Ma, J.-N., Del Tredici, A. L., Currier, E. A., Gardell, L. R., Tabatabaei, A., Craig, D., McFarland, K., Ott, T. R., Piu, F., Burstein, E. S. & Olsson, R. (2009). J. Med. Chem. 52, 1975-1982.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ravikumar, K. & Sridhar, B. (2005). Acta Cryst. E61, o3245-o3248.  [CSD] [CrossRef] [details]
Riedel, M., Mueller, N., Strassnig, M., Spellman, I., Severus, E. & Moeller, H.-J. (2007). Neuropsyc. Dis. Treat. 3, 219-235.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Warawa, E. J., Migler, B. M., Ohnmacht, C. J., Needles, A. L., Gatos, G. C., Mclaren, F. M., Nelson, C. L. & Kirkland, K. M. (2001). J. Med. Chem. 44, 372-389.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3133-o3134   [ doi:10.1107/S1600536812042328 ]

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