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

Altamura, M.; Guidi, A.; Jierry, L.; Paoli, P.; Rossi, P.

doi:10.1107/S1600536812042328

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.086
Data-to-parameter ratio = 13.1
Details

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

Maria Altamura,^a Antonio Guidi,^a Loic Jierry,^b Paola Paoli ^c ^* and Patrizia Rossi ^c

^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 C_aromatic-HN 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); Patchett & Nargund (2000); Fedi et al. (2008). For the clinical use of dibenzothiazepine derivatives, see: Ganesh et al. (2011); Pettersson et al. (2009); Riedel et al. (2007); Warawa et al. (2001). For structure-property relationships in (6,7,6)-tricyclic ring systems, see: Ravikumar & Sridhar (2005); Altamura et al. (2008, 2009, 2011). For geometrical data and descriptors, see: Duax et al. (1976); Bertolasi et al. (1982); Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₈N₂S
M_r = 282.40
Monoclinic, P 2₁ /c
a = 12.0137 (2) Å
b = 8.2257 (1) Å
c = 15.0513 (2) Å
= 102.952 (1)°
V = 1449.54 (4) Å³
Z = 4
Cu K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.722, T_max = 0.945
6173 measured reflections
2364 independent reflections
1837 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.086
S = 1.05
2364 reflections
181 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8-C12 ring.

D-HA	D-H	HA	DA	D-HA
C5-H5N1ⁱ	0.95	2.70	3.576 (2)	154
C4-H4Cgⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995).

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

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organic compounds