1-(4-Chloro-3-fluoro­phen­yl)-2-[(3-phenyl­isoquinolin-1-yl)sulfan­yl]ethanone

P Manivel; Venkatesha R Hathwar; T Maiyalagan; N Burcu Arslan; F Nawaz Khan

doi:10.1107/S1600536809001573

. 2009 Jan 17;65(Pt 2):o334. doi: 10.1107/S1600536809001573

1-(4-Chloro-3-fluorophenyl)-2-[(3-phenylisoquinolin-1-yl)sulfanyl]ethanone

P Manivel ^a, Venkatesha R Hathwar ^b, T Maiyalagan ^a, N Burcu Arslan ^c, F Nawaz Khan ^a,^*

PMCID: PMC2968360 PMID: 21581937

Abstract

In the title compound, C₂₃H₁₅ClFNOS, the isoquinoline system and the 4-chloro-3-fluorophenyl ring are aligned at 80.4 (1)°. The dihedral angle between the isoquinoline system and the pendant (unsubstituted) phenyl ring is 19.91 (1)°.

Related literature

For related structures, see: Hathwar et al. (2008 ▶); Manivel et al. (2009a ▶,b ▶).

Experimental

Crystal data

C₂₃H₁₅ClFNOS
M _r = 407.87
Orthorhombic,
a = 16.9008 (11) Å
b = 9.8036 (7) Å
c = 23.3226 (16) Å
V = 3864.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 290 (2) K
0.24 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.925, T _max = 0.965
27428 measured reflections
3595 independent reflections
2424 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.128
S = 1.04
3595 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001573/ng2534sup1.cif

e-65-0o334-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001573/ng2534Isup2.hkl

e-65-0o334-Isup2.hkl^{(172.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at the IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

In compound (I), the S atom also located in the plane. The F atom deviates by 0.014 A from mean plane of phenyl ring containing F and Cl atoms. In this ring F– C and Cl—C bond distances are 1.348 (4) A, 1.727 (3) A, respectively. The orientation of isoquinoline ring system with respect to the another phenyl ring is given by the torsion angles for N1—C2—C10—C15 and C3—C2—C10—C11 are respectively -160.1 (2)°, -163.1 (3)° similarly for C16—S1—C1—N1 and C16—S1—C1—C8 are respectively -0.8 (2)° and 179.56 (19)° (Table 1).

Experimental

3-Phenylisoquinoline-1-thiol and 2-bromo-1-(3-fluoro-4-chlorophenyl)ethanone were mixed in the ratio 1:1.05 equivalents with ethanol in a round bottom flask. Then it was heated under nitrogen atmosphere on an oil bath at 323 K. After 2 h, the products were filtered and dissolved in chloroform. Further, it was washed with water, dried and concentrated. The single-crystal for X-ray structue anlaysis was obtained from ether solution by slow evaporation.