2-[4-Chloro-3-(4-ethoxy­benz­yl)phen­yl]-1,3-dithiane

Samas, B.; Préville, C.; Thuma, B.A.; Mascitti, V.

doi:10.1107/S1600536810017393

Volume 66
Part 6
Page o1386
June 2010

Received 26 March 2010
Accepted 11 May 2010
Online 19 May 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 15.6
Details

2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-1,3-dithiane

Brian Samas,^a ^* Cathy Préville,^b Benjamin A Thuma ^b and Vincent Mascitti ^b

^aPharmaceutical Sciences, Pfizer Global Research & Development, Groton Laboratories, Eastern Point Rd, Groton, CT 06340, USA, and ^bCVMED Medicinal Chemistry, Pfizer Global Research & Development, Groton Laboratories, Eastern Point Rd, Groton, CT 06340, USA
Correspondence e-mail: brian.samas@pfizer.com

In the title compound, C₁₉H₂₁ClOS₂, the dithiane ring adopts a chair conformation. The dihedral angle between the benzene rings is 87.88 (4)°. In the crystal, inversion dimmers linked by pairs of C-HO interactions occur.

Related literature

For a related structure, see: Fun et al. (2009). For diarylmethane motifs, see: Xu et al. (2009).

Experimental

Crystal data

C₁₉H₂₁ClOS₂
M_r = 364.93
Monoclinic, P 2₁ /c
a = 15.8214 (3) Å
b = 12.2444 (2) Å
c = 9.4191 (2) Å
= 100.715 (1)°
V = 1792.89 (6) Å³
Z = 4
Cu K radiation
= 4.06 mm^-1
T = 100 K
0.19 × 0.13 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.513, T_max = 0.888
13885 measured reflections
3257 independent reflections
3040 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.095
S = 1.06
3257 reflections
209 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19AO1ⁱ	0.97	2.40	3.367 (2)	173
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2206 ).

References

Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Jebas, S. R., Maity, A. C., Das, N. K. & Goswami, S. (2009). Acta Cryst. E65, o891.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xu, B., Lv, B., Feng, Y., Xu, G., Du, J., Welihinda, A., Sheng, Z., Seed, B. & Chen, Y. (2009). Bioorg. Med. Chem. Lett. 19, 5632-5635.

organic compounds