supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, o334    [ doi:10.1107/S1600536809001573 ]

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

P. Manivel, V. R. Hathwar, T. Maiyalagan, N. B. Arslan and F. Nawaz Khan

Abstract top

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)°.

Comment top

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).

Related literature top

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

Experimental top

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.

Refinement top

All the H atoms in (I) were positioned geometrically and refined using a riding model with C—H bond lenghts of 0.93 Å and 0.97 Å for aromatic and for methylene H atoms respectively and Uiso(H) = 1.2Ueq(C) for all carbon bound H atoms.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of the asymmetric unit of (I) with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing diagram of (I).The dotted lines indicate intermolecular C—H···O hydrogen bonds. All H atoms have been omitted for clarity.
1-(4-Chloro-3-fluorophenyl)-2-[(3-phenylisoquinolin-1-yl)sulfanyl]ethanone top
Crystal data top
C23H15ClFNOSF(000) = 1680
Mr = 407.87Dx = 1.402 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3595 reflections
a = 16.9008 (11) Åθ = 1.8–25.5°
b = 9.8036 (7) ŵ = 0.33 mm−1
c = 23.3226 (16) ÅT = 290 K
V = 3864.3 (5) Å3Block, colourless
Z = 80.24 × 0.18 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3595 independent reflections
Radiation source: fine-focus sealed tube2424 reflections with I > 2σ(I)
graphiteRint = 0.063
φ and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −18→20
Tmin = 0.925, Tmax = 0.965k = −11→11
27428 measured reflectionsl = −28→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0566P)2 + 1.1665P]
where P = (Fo2 + 2Fc2)/3
3595 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C23H15ClFNOSV = 3864.3 (5) Å3
Mr = 407.87Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 16.9008 (11) ŵ = 0.33 mm−1
b = 9.8036 (7) ÅT = 290 K
c = 23.3226 (16) Å0.24 × 0.18 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3595 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2424 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.965Rint = 0.063
27428 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.128Δρmax = 0.32 e Å−3
S = 1.04Δρmin = −0.19 e Å−3
3595 reflectionsAbsolute structure: ?
253 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.07142 (12)0.8183 (2)0.28005 (9)0.0633 (6)
F10.09785 (13)0.8393 (2)0.06905 (9)0.1057 (7)
S10.03138 (4)0.61721 (7)0.37120 (3)0.0495 (2)
Cl1−0.02952 (8)0.70329 (14)0.00961 (4)0.1221 (5)
N10.12270 (12)0.4853 (2)0.29715 (9)0.0399 (5)
C10.11497 (15)0.5201 (2)0.35092 (11)0.0393 (6)
C20.18572 (14)0.4054 (2)0.28104 (11)0.0405 (6)
C30.24276 (16)0.3684 (3)0.31906 (11)0.0474 (7)
H30.28610.31800.30660.057*
C40.29398 (18)0.3701 (3)0.41884 (13)0.0593 (8)
H40.33840.32050.40790.071*
C50.2845 (2)0.4076 (3)0.47468 (14)0.0688 (9)
H50.32250.38270.50160.083*
C60.2188 (2)0.4828 (3)0.49197 (13)0.0643 (9)
H60.21350.50850.53020.077*
C70.16226 (18)0.5189 (3)0.45299 (12)0.0538 (7)
H70.11800.56760.46500.065*
C80.17027 (16)0.4832 (2)0.39492 (11)0.0422 (6)
C90.23657 (16)0.4063 (3)0.37753 (11)0.0451 (6)
C100.18550 (14)0.3638 (2)0.21970 (11)0.0419 (6)
C110.13897 (17)0.4309 (3)0.18011 (12)0.0515 (7)
H110.10850.50460.19210.062*
C120.13641 (19)0.3920 (3)0.12340 (12)0.0597 (8)
H120.10460.43920.09760.072*
C130.18110 (19)0.2828 (3)0.10499 (13)0.0641 (9)
H130.18050.25690.06660.077*
C140.22641 (19)0.2130 (4)0.14375 (14)0.0715 (10)
H140.25560.13790.13170.086*
C150.22938 (17)0.2524 (3)0.20044 (13)0.0598 (8)
H150.26090.20420.22610.072*
C16−0.01524 (15)0.6351 (3)0.30300 (11)0.0439 (6)
H16A−0.01770.54610.28490.053*
H16B−0.06920.66590.30890.053*
C170.02538 (15)0.7327 (2)0.26264 (12)0.0426 (6)
C180.00791 (15)0.7226 (2)0.20013 (12)0.0422 (6)
C190.05916 (17)0.7874 (3)0.16253 (13)0.0520 (7)
H190.10200.83660.17660.062*
C200.0465 (2)0.7788 (3)0.10523 (15)0.0647 (9)
C21−0.0164 (2)0.7098 (4)0.08298 (14)0.0679 (9)
C22−0.0680 (2)0.6464 (3)0.11953 (15)0.0714 (9)
H22−0.11160.60000.10490.086*
C23−0.05585 (18)0.6510 (3)0.17826 (13)0.0572 (8)
H23−0.09040.60620.20290.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0674 (14)0.0532 (12)0.0694 (14)−0.0142 (11)−0.0162 (11)−0.0004 (10)
F10.1066 (17)0.1363 (19)0.0742 (14)−0.0033 (15)0.0267 (12)0.0272 (13)
S10.0554 (5)0.0517 (4)0.0412 (4)0.0142 (3)0.0010 (3)−0.0073 (3)
Cl10.1660 (12)0.1504 (11)0.0500 (6)0.0166 (9)−0.0195 (6)0.0006 (6)
N10.0408 (13)0.0394 (12)0.0396 (12)0.0018 (10)0.0016 (10)−0.0030 (9)
C10.0454 (16)0.0322 (13)0.0404 (15)−0.0012 (11)0.0021 (12)−0.0003 (11)
C20.0372 (15)0.0380 (14)0.0462 (15)−0.0010 (11)0.0047 (12)−0.0020 (12)
C30.0381 (15)0.0473 (15)0.0570 (17)0.0062 (12)0.0002 (14)−0.0042 (14)
C40.0579 (19)0.0559 (18)0.064 (2)0.0096 (15)−0.0138 (16)0.0034 (16)
C50.081 (2)0.068 (2)0.058 (2)0.0080 (19)−0.0261 (18)0.0111 (17)
C60.090 (2)0.0590 (19)0.0443 (17)0.0110 (18)−0.0115 (17)0.0026 (14)
C70.070 (2)0.0462 (16)0.0448 (17)0.0078 (15)−0.0052 (14)0.0015 (13)
C80.0501 (16)0.0346 (13)0.0419 (15)−0.0011 (12)−0.0037 (12)0.0025 (11)
C90.0481 (16)0.0368 (14)0.0505 (16)−0.0013 (12)−0.0068 (13)0.0021 (12)
C100.0368 (15)0.0425 (14)0.0464 (16)−0.0034 (12)0.0067 (12)−0.0055 (12)
C110.0665 (19)0.0400 (15)0.0479 (17)0.0057 (14)0.0020 (15)−0.0024 (13)
C120.077 (2)0.0564 (17)0.0457 (17)0.0053 (16)−0.0019 (15)0.0004 (14)
C130.065 (2)0.081 (2)0.0468 (18)0.0032 (18)0.0075 (16)−0.0157 (16)
C140.058 (2)0.091 (3)0.065 (2)0.0256 (19)0.0001 (17)−0.0299 (19)
C150.0466 (18)0.074 (2)0.0585 (19)0.0217 (16)−0.0017 (14)−0.0164 (16)
C160.0429 (16)0.0415 (15)0.0472 (16)0.0076 (12)0.0010 (12)−0.0031 (12)
C170.0383 (15)0.0353 (14)0.0543 (17)0.0055 (12)−0.0039 (13)−0.0023 (12)
C180.0410 (15)0.0341 (13)0.0514 (17)0.0041 (12)−0.0020 (13)0.0016 (12)
C190.0485 (17)0.0474 (17)0.060 (2)0.0057 (13)0.0024 (14)0.0034 (14)
C200.069 (2)0.069 (2)0.056 (2)0.0130 (18)0.0129 (18)0.0134 (16)
C210.087 (3)0.072 (2)0.0453 (18)0.018 (2)−0.0032 (18)0.0037 (16)
C220.081 (2)0.070 (2)0.064 (2)−0.0032 (18)−0.0258 (19)−0.0049 (17)
C230.0612 (19)0.0512 (17)0.059 (2)−0.0033 (14)−0.0071 (16)0.0041 (14)
Geometric parameters (Å, °) top
O1—C171.215 (3)C10—C151.395 (3)
F1—C201.348 (4)C11—C121.377 (4)
S1—C11.768 (3)C11—H110.9300
S1—C161.784 (3)C12—C131.378 (4)
Cl1—C211.727 (3)C12—H120.9300
N1—C11.306 (3)C13—C141.368 (4)
N1—C21.375 (3)C13—H130.9300
C1—C81.434 (3)C14—C151.378 (4)
C2—C31.359 (3)C14—H140.9300
C2—C101.487 (3)C15—H150.9300
C3—C91.417 (3)C16—C171.508 (4)
C3—H30.9300C16—H16A0.9700
C4—C51.363 (4)C16—H16B0.9700
C4—C91.413 (4)C17—C181.491 (4)
C4—H40.9300C18—C231.383 (4)
C5—C61.392 (4)C18—C191.387 (4)
C5—H50.9300C19—C201.356 (4)
C6—C71.366 (4)C19—H190.9300
C6—H60.9300C20—C211.363 (5)
C7—C81.405 (4)C21—C221.369 (5)
C7—H70.9300C22—C231.386 (4)
C8—C91.410 (3)C22—H220.9300
C10—C111.380 (4)C23—H230.9300
C1—S1—C1699.63 (12)C13—C12—H12120.1
C1—N1—C2119.3 (2)C14—C13—C12119.3 (3)
N1—C1—C8123.8 (2)C14—C13—H13120.3
N1—C1—S1118.51 (19)C12—C13—H13120.3
C8—C1—S1117.71 (19)C13—C14—C15120.9 (3)
C3—C2—N1121.5 (2)C13—C14—H14119.5
C3—C2—C10123.8 (2)C15—C14—H14119.5
N1—C2—C10114.7 (2)C14—C15—C10120.6 (3)
C2—C3—C9120.4 (2)C14—C15—H15119.7
C2—C3—H3119.8C10—C15—H15119.7
C9—C3—H3119.8C17—C16—S1114.70 (19)
C5—C4—C9120.2 (3)C17—C16—H16A108.6
C5—C4—H4119.9S1—C16—H16A108.6
C9—C4—H4119.9C17—C16—H16B108.6
C4—C5—C6120.9 (3)S1—C16—H16B108.6
C4—C5—H5119.6H16A—C16—H16B107.6
C6—C5—H5119.6O1—C17—C18120.0 (2)
C7—C6—C5120.2 (3)O1—C17—C16121.5 (3)
C7—C6—H6119.9C18—C17—C16118.6 (2)
C5—C6—H6119.9C23—C18—C19119.1 (3)
C6—C7—C8120.6 (3)C23—C18—C17123.3 (3)
C6—C7—H7119.7C19—C18—C17117.7 (2)
C8—C7—H7119.7C20—C19—C18119.7 (3)
C7—C8—C9119.2 (2)C20—C19—H19120.1
C7—C8—C1124.3 (2)C18—C19—H19120.1
C9—C8—C1116.5 (2)F1—C20—C19119.2 (3)
C8—C9—C4118.9 (3)F1—C20—C21118.8 (3)
C8—C9—C3118.4 (2)C19—C20—C21122.0 (3)
C4—C9—C3122.7 (3)C20—C21—C22119.0 (3)
C11—C10—C15117.4 (2)C20—C21—Cl1119.7 (3)
C11—C10—C2120.9 (2)C22—C21—Cl1121.2 (3)
C15—C10—C2121.6 (2)C21—C22—C23120.4 (3)
C12—C11—C10121.9 (3)C21—C22—H22119.8
C12—C11—H11119.0C23—C22—H22119.8
C10—C11—H11119.0C18—C23—C22119.8 (3)
C11—C12—C13119.8 (3)C18—C23—H23120.1
C11—C12—H12120.1C22—C23—H23120.1
C2—N1—C1—C82.0 (4)C15—C10—C11—C12−1.1 (4)
C2—N1—C1—S1−177.53 (17)C2—C10—C11—C12−178.4 (3)
C16—S1—C1—N1−0.8 (2)C10—C11—C12—C130.2 (4)
C16—S1—C1—C8179.56 (19)C11—C12—C13—C141.2 (5)
C1—N1—C2—C3−4.0 (4)C12—C13—C14—C15−1.6 (5)
C1—N1—C2—C10175.8 (2)C13—C14—C15—C100.6 (5)
N1—C2—C3—C93.1 (4)C11—C10—C15—C140.7 (4)
C10—C2—C3—C9−176.7 (2)C2—C10—C15—C14178.0 (3)
C9—C4—C5—C6−0.5 (5)C1—S1—C16—C17−73.20 (19)
C4—C5—C6—C70.7 (5)S1—C16—C17—O1−19.3 (3)
C5—C6—C7—C8−1.2 (4)S1—C16—C17—C18160.73 (18)
C6—C7—C8—C91.6 (4)O1—C17—C18—C23−164.7 (3)
C6—C7—C8—C1−178.2 (3)C16—C17—C18—C2315.2 (4)
N1—C1—C8—C7−179.4 (2)O1—C17—C18—C1916.0 (4)
S1—C1—C8—C70.1 (3)C16—C17—C18—C19−164.1 (2)
N1—C1—C8—C90.7 (4)C23—C18—C19—C20−0.6 (4)
S1—C1—C8—C9−179.71 (18)C17—C18—C19—C20178.7 (2)
C7—C8—C9—C4−1.5 (4)C18—C19—C20—F1−178.3 (2)
C1—C8—C9—C4178.4 (2)C18—C19—C20—C211.2 (5)
C7—C8—C9—C3178.5 (2)F1—C20—C21—C22179.0 (3)
C1—C8—C9—C3−1.6 (3)C19—C20—C21—C22−0.5 (5)
C5—C4—C9—C80.9 (4)F1—C20—C21—Cl1−0.8 (4)
C5—C4—C9—C3−179.1 (3)C19—C20—C21—Cl1179.7 (2)
C2—C3—C9—C8−0.2 (4)C20—C21—C22—C23−0.8 (5)
C2—C3—C9—C4179.8 (3)Cl1—C21—C22—C23179.0 (2)
C3—C2—C10—C11−163.1 (3)C19—C18—C23—C22−0.7 (4)
N1—C2—C10—C1117.1 (3)C17—C18—C23—C22−180.0 (3)
C3—C2—C10—C1519.7 (4)C21—C22—C23—C181.4 (5)
N1—C2—C10—C15−160.1 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···S10.932.683.076 (3)107
C11—H11···N10.932.472.795 (4)101
Acknowledgements top

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. F.NK thanks the DST for Fast Track Proposal funding.

references
References top

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Hathwar, V. R., Prabakaran, K., Subashini, R., Manivel, P. & Khan, F. N. (2008). Acta Cryst. E64, o2295.

Manivel, P., Hathwar, V. R., Nithya, P., Prabakaran, K. & Khan, F. N. (2009a). Acta Cryst. E65, o137–138.

Manivel, P., Hathwar, V. R., Nithya, P., Subashini, R. & Nawaz Khan, F. (2009b). Acta Cryst. E65, o254.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.