Lurasidone hydro­chloride

Zhang, H.; Wang, H.; Zhu, X.; Yuan, Z.; Jiang, H.

doi:10.1107/S1600536812012883

Volume 68
Part 5
Page o1357
May 2012

Received 29 February 2012
Accepted 24 March 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.108
Data-to-parameter ratio = 16.4
Details

Lurasidone hydrochloride

Hua Zhang,^a Hubo Wang,^a Xueyan Zhu,^a Zhedong Yuan ^a ^* and Huijuan Jiang ^a

^aShanghai Institute of Pharmaceutical Industry, No. 1111, North ZhongShan No.1 Road, HongKou District, Shanghai 200437, People's Republic of China
Correspondence e-mail: gongyierzu@126.com

In the crystal structure of the title compound, C₂₈H₃₇N₄O₂S⁺·Cl^- [systematic name: 4-(1,2-benzothiazol-3-yl)-1-({2-[(3,5-dioxo-4-azatricyclo[5.2.1.0^2,6]decan-4-yl)methyl]cyclohexyl}methyl)piperazin-1-ium chloride], the anions and cations are linked by N-HCl hydrogen bonds. The crystal structure is further stabilized by C-H [pi] and C-HO interactions.

Related literature

For the background to the biological activity of the title compound, an antipsychotic drug, see: Ishibashi et al. (2002); Ishiyama et al. (2003); Ohno et al. (1997).

Experimental

Crystal data

C₂₈H₃₇N₄O₂S⁺·Cl^-
M_r = 529.13
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.2039 (10) Å
b = 12.2665 (11) Å
c = 19.9774 (18) Å
V = 2745.5 (4) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 293 K
0.22 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.452, T_max = 1.000
15020 measured reflections
5384 independent reflections
4649 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.108
S = 1.10
5384 reflections
329 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.14 e Å^-3
Absolute structure: Flack (1983), 2338 Friedel pairs
Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the S1/ N4/C22/C23/C28 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2ACl1	0.80 (2)	2.15 (2)	2.9426 (19)	168 (2)
C21-H21AO1ⁱ	0.97	2.38	3.289 (3)	156
C5-H5ACgⁱⁱ	0.97	2.89	3.802 (4)	157
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5835 ).

Acknowledgements

The authors thank the Shanghai Institute of Organic Chemistry for providing the infrastructure.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Ishibashi, T., Horisawa, T., Yabuuchi, K., Tagashira, R. & Ohno, Y. (2002). Soc. Neurosci. Abstr. 894, 7.
Ishiyama, T., Matsumoto, Y., Tokuda, K., Horisawa, T., Tagashira, R., Toma, S. & Ohno, Y. (2003). Soc. Neurosci. Abstr. 835, 22.
Ohno, Y., Ishida, K., Ishibashi, T., Tojima, R., Yasui, J. & Nakamura, M. (1997). Int. Acad. Biomed. Drug Res. 11, 287-287.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds