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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o334.
Published online 2009 January 17. doi:  10.1107/S1600536809001573
PMCID: PMC2968360

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

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 [triangle]); Manivel et al. (2009a [triangle],b [triangle]).

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Object name is e-65-0o334-scheme1.jpg

Experimental

Crystal data

  • C23H15ClFNOS
  • M r = 407.87
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o334-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.19 e Å−3

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

Supplementary Material

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

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

Refinement

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.

Figures

Fig. 1.
ORTEP diagram of the asymmetric unit of (I) with 50% probability displacement ellipsoids.
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.

Crystal data

C23H15ClFNOSF(000) = 1680
Mr = 407.87Dx = 1.402 Mg m3
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 mm1
c = 23.3226 (16) ÅT = 290 K
V = 3864.3 (5) Å3Block, colourless
Z = 80.24 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer3595 independent reflections
Radiation source: fine-focus sealed tube2424 reflections with I > 2σ(I)
graphiteRint = 0.063
[var phi] 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

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

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)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···S10.932.683.076 (3)107
C11—H11···N10.932.472.795 (4)101

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2534).

References

  • 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. [PMC free article] [PubMed]
  • Manivel, P., Hathwar, V. R., Nithya, P., Prabakaran, K. & Khan, F. N. (2009a). Acta Cryst. E65, o137–o138. [PMC free article] [PubMed]
  • Manivel, P., Hathwar, V. R., Nithya, P., Subashini, R. & Nawaz Khan, F. (2009b). Acta Cryst. E65, o254. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

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