Acta Cryst. (2009). E65, o254 [ doi:10.1107/S1600536809000257 ]
The title compound, C23H16ClNOS, exhibits dihedral angles of 11.73 (1) and 66.07 (1)°, respectively, between the mean plane of the isoquinoline system and the attached phenyl ring, and between the isoquinoline system and the chlorophenyl ring. The dihedral angle between the phenyl and chlorophenyl rings is 54.66 (1)°.
3-Phenylisoquinoline-1-thiol and 2-bromo-1-(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.
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.
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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./ng2532fig1thm.gif)
| Fig. 1. ORTEP diagram of the asymmetric unit of (I) with 50% probability displacement ellipsoids. |
![[Figure 2]](./ng2532fig2thm.gif)
| 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. |
| C23H16ClNOS | F(000) = 1616 |
| Mr = 389.89 | Dx = 1.371 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 871 reflections |
| a = 9.5874 (14) Å | θ = 1.9–25.0° |
| b = 17.888 (3) Å | µ = 0.33 mm−1 |
| c = 22.025 (3) Å | T = 290 K |
| V = 3777.3 (10) Å3 | Rod, colourless |
| Z = 8 | 0.26 × 0.20 × 0.14 mm |
| Bruker SMART CCD area-detector diffractometer | 3332 independent reflections |
| Radiation source: fine-focus sealed tube | 1915 reflections with I > 2σ(I) |
| graphite | Rint = 0.116 |
| φ and ω scans | θmax = 25.0°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.901, Tmax = 0.956 | k = −21→21 |
| 25674 measured reflections | l = −24→26 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.125 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0308P)2 + 0.7191P] where P = (Fo2 + 2Fc2)/3 |
| 3332 reflections | (Δ/σ)max < 0.001 |
| 244 parameters | Δρmax = 0.23 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
| C23H16ClNOS | V = 3777.3 (10) Å3 |
| Mr = 389.89 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 9.5874 (14) Å | µ = 0.33 mm−1 |
| b = 17.888 (3) Å | T = 290 K |
| c = 22.025 (3) Å | 0.26 × 0.20 × 0.14 mm |
| Bruker SMART CCD area-detector diffractometer | 3332 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1915 reflections with I > 2σ(I) |
| Tmin = 0.901, Tmax = 0.956 | Rint = 0.116 |
| 25674 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
| wR(F2) = 0.125 | Δρmax = 0.23 e Å−3 |
| S = 1.04 | Δρmin = −0.23 e Å−3 |
| 3332 reflections | Absolute structure: ? |
| 244 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | −0.16890 (17) | 0.07371 (9) | 0.25163 (6) | 0.1375 (6) | |
| S1 | −0.09127 (10) | 0.34062 (5) | −0.06818 (5) | 0.0545 (3) | |
| O1 | 0.0295 (2) | 0.19469 (13) | −0.02148 (12) | 0.0588 (7) | |
| N1 | 0.0851 (3) | 0.36685 (14) | 0.02265 (13) | 0.0406 (7) | |
| C1 | 0.0416 (3) | 0.39062 (18) | −0.03051 (16) | 0.0401 (9) | |
| C2 | 0.1941 (3) | 0.40302 (18) | 0.05067 (15) | 0.0390 (9) | |
| C3 | 0.2597 (4) | 0.46147 (19) | 0.02355 (16) | 0.0460 (9) | |
| H3 | 0.3348 | 0.4841 | 0.0430 | 0.055* | |
| C4 | 0.2805 (4) | 0.54850 (19) | −0.06405 (19) | 0.0554 (10) | |
| H4 | 0.3564 | 0.5724 | −0.0463 | 0.067* | |
| C5 | 0.2337 (5) | 0.5720 (2) | −0.1189 (2) | 0.0644 (12) | |
| H5 | 0.2784 | 0.6111 | −0.1387 | 0.077* | |
| C6 | 0.1184 (5) | 0.5375 (2) | −0.14581 (18) | 0.0665 (12) | |
| H6 | 0.0862 | 0.5543 | −0.1832 | 0.080* | |
| C7 | 0.0532 (4) | 0.47981 (19) | −0.11778 (17) | 0.0570 (11) | |
| H7 | −0.0237 | 0.4575 | −0.1360 | 0.068* | |
| C8 | 0.1007 (4) | 0.45349 (17) | −0.06155 (16) | 0.0410 (8) | |
| C9 | 0.2160 (4) | 0.48838 (17) | −0.03338 (16) | 0.0428 (9) | |
| C10 | 0.2362 (4) | 0.3727 (2) | 0.11049 (16) | 0.0439 (9) | |
| C11 | 0.3618 (4) | 0.3927 (2) | 0.13781 (17) | 0.0656 (12) | |
| H11 | 0.4201 | 0.4267 | 0.1184 | 0.079* | |
| C12 | 0.4012 (5) | 0.3632 (3) | 0.19275 (19) | 0.0801 (13) | |
| H12 | 0.4854 | 0.3779 | 0.2100 | 0.096* | |
| C13 | 0.3193 (5) | 0.3129 (3) | 0.22247 (19) | 0.0778 (13) | |
| H13 | 0.3463 | 0.2933 | 0.2598 | 0.093* | |
| C14 | 0.1957 (5) | 0.2919 (2) | 0.19589 (19) | 0.0748 (13) | |
| H14 | 0.1390 | 0.2570 | 0.2152 | 0.090* | |
| C15 | 0.1543 (4) | 0.3218 (2) | 0.14102 (17) | 0.0594 (11) | |
| H15 | 0.0694 | 0.3072 | 0.1243 | 0.071* | |
| C16 | −0.1538 (3) | 0.28339 (18) | −0.00757 (16) | 0.0486 (10) | |
| H16A | −0.1685 | 0.3150 | 0.0276 | 0.058* | |
| H16B | −0.2440 | 0.2634 | −0.0193 | 0.058* | |
| C17 | −0.0618 (4) | 0.21887 (18) | 0.01117 (18) | 0.0454 (10) | |
| C18 | −0.0910 (4) | 0.18457 (17) | 0.07171 (18) | 0.0470 (9) | |
| C19 | −0.2116 (4) | 0.1996 (2) | 0.10416 (18) | 0.0529 (10) | |
| H19 | −0.2767 | 0.2330 | 0.0885 | 0.064* | |
| C20 | −0.2360 (4) | 0.1656 (3) | 0.15937 (19) | 0.0693 (12) | |
| H20 | −0.3179 | 0.1754 | 0.1806 | 0.083* | |
| C21 | −0.1389 (6) | 0.1174 (3) | 0.18275 (19) | 0.0769 (13) | |
| C22 | −0.0177 (5) | 0.1022 (2) | 0.1514 (2) | 0.0762 (13) | |
| H22 | 0.0480 | 0.0695 | 0.1675 | 0.091* | |
| C23 | 0.0055 (4) | 0.1354 (2) | 0.0962 (2) | 0.0630 (11) | |
| H23 | 0.0869 | 0.1249 | 0.0750 | 0.076* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1541 (14) | 0.1891 (16) | 0.0694 (9) | −0.0056 (13) | −0.0200 (9) | 0.0362 (10) |
| S1 | 0.0462 (6) | 0.0542 (5) | 0.0632 (7) | −0.0085 (5) | −0.0116 (6) | −0.0032 (5) |
| O1 | 0.0391 (15) | 0.0504 (15) | 0.087 (2) | 0.0030 (12) | 0.0112 (15) | −0.0136 (14) |
| N1 | 0.0357 (17) | 0.0379 (15) | 0.0481 (19) | −0.0030 (14) | 0.0007 (16) | −0.0072 (14) |
| C1 | 0.032 (2) | 0.038 (2) | 0.050 (2) | 0.0031 (16) | 0.0014 (18) | −0.0074 (18) |
| C2 | 0.036 (2) | 0.037 (2) | 0.045 (2) | 0.0020 (17) | 0.0029 (17) | −0.0125 (17) |
| C3 | 0.044 (2) | 0.040 (2) | 0.054 (2) | −0.0063 (17) | −0.005 (2) | −0.0126 (19) |
| C4 | 0.055 (3) | 0.040 (2) | 0.071 (3) | −0.0047 (19) | 0.010 (2) | −0.005 (2) |
| C5 | 0.074 (3) | 0.043 (2) | 0.076 (3) | −0.001 (2) | 0.017 (3) | 0.006 (2) |
| C6 | 0.084 (3) | 0.058 (3) | 0.058 (3) | 0.005 (2) | 0.003 (3) | 0.011 (2) |
| C7 | 0.060 (3) | 0.048 (2) | 0.063 (3) | 0.000 (2) | −0.004 (2) | 0.003 (2) |
| C8 | 0.042 (2) | 0.0353 (18) | 0.046 (2) | 0.0077 (17) | 0.0068 (19) | −0.0053 (18) |
| C9 | 0.043 (2) | 0.0303 (19) | 0.055 (2) | −0.0010 (17) | 0.007 (2) | −0.0096 (18) |
| C10 | 0.040 (2) | 0.047 (2) | 0.045 (2) | −0.0009 (18) | 0.001 (2) | −0.0121 (19) |
| C11 | 0.057 (3) | 0.087 (3) | 0.054 (3) | −0.015 (2) | −0.002 (2) | 0.004 (2) |
| C12 | 0.064 (3) | 0.119 (4) | 0.057 (3) | −0.018 (3) | −0.013 (3) | 0.003 (3) |
| C13 | 0.082 (4) | 0.101 (4) | 0.050 (3) | −0.005 (3) | −0.010 (3) | 0.006 (3) |
| C14 | 0.084 (3) | 0.078 (3) | 0.063 (3) | −0.016 (3) | −0.009 (3) | 0.019 (3) |
| C15 | 0.060 (3) | 0.059 (3) | 0.058 (3) | −0.009 (2) | −0.011 (2) | 0.005 (2) |
| C16 | 0.033 (2) | 0.044 (2) | 0.068 (3) | −0.0058 (17) | −0.0008 (19) | −0.0072 (19) |
| C17 | 0.031 (2) | 0.0346 (19) | 0.071 (3) | −0.0067 (17) | −0.005 (2) | −0.011 (2) |
| C18 | 0.039 (2) | 0.0350 (18) | 0.067 (3) | −0.0037 (18) | −0.005 (2) | −0.012 (2) |
| C19 | 0.047 (3) | 0.053 (2) | 0.058 (3) | −0.002 (2) | −0.008 (2) | −0.008 (2) |
| C20 | 0.059 (3) | 0.091 (3) | 0.058 (3) | −0.009 (3) | −0.006 (3) | −0.013 (3) |
| C21 | 0.084 (4) | 0.090 (3) | 0.057 (3) | −0.012 (3) | −0.019 (3) | −0.003 (3) |
| C22 | 0.077 (4) | 0.062 (3) | 0.090 (4) | 0.004 (3) | −0.030 (3) | 0.007 (3) |
| C23 | 0.050 (3) | 0.050 (2) | 0.089 (3) | 0.002 (2) | −0.008 (2) | −0.001 (2) |
| Cl1—C21 | 1.731 (4) | C11—C12 | 1.373 (5) |
| S1—C1 | 1.764 (3) | C11—H11 | 0.9300 |
| S1—C16 | 1.786 (3) | C12—C13 | 1.362 (5) |
| O1—C17 | 1.212 (4) | C12—H12 | 0.9300 |
| N1—C1 | 1.314 (4) | C13—C14 | 1.374 (5) |
| N1—C2 | 1.375 (4) | C13—H13 | 0.9300 |
| C1—C8 | 1.433 (4) | C14—C15 | 1.379 (5) |
| C2—C3 | 1.359 (4) | C14—H14 | 0.9300 |
| C2—C10 | 1.481 (4) | C15—H15 | 0.9300 |
| C3—C9 | 1.407 (4) | C16—C17 | 1.510 (4) |
| C3—H3 | 0.9300 | C16—H16A | 0.9700 |
| C4—C5 | 1.355 (5) | C16—H16B | 0.9700 |
| C4—C9 | 1.412 (4) | C17—C18 | 1.494 (5) |
| C4—H4 | 0.9300 | C18—C23 | 1.385 (5) |
| C5—C6 | 1.398 (5) | C18—C19 | 1.385 (5) |
| C5—H5 | 0.9300 | C19—C20 | 1.380 (5) |
| C6—C7 | 1.355 (5) | C19—H19 | 0.9300 |
| C6—H6 | 0.9300 | C20—C21 | 1.369 (6) |
| C7—C8 | 1.401 (4) | C20—H20 | 0.9300 |
| C7—H7 | 0.9300 | C21—C22 | 1.380 (6) |
| C8—C9 | 1.413 (4) | C22—C23 | 1.371 (5) |
| C10—C15 | 1.378 (4) | C22—H22 | 0.9300 |
| C10—C11 | 1.392 (5) | C23—H23 | 0.9300 |
| C1—S1—C16 | 100.46 (17) | C11—C12—H12 | 119.4 |
| C1—N1—C2 | 119.3 (3) | C12—C13—C14 | 118.2 (4) |
| N1—C1—C8 | 123.6 (3) | C12—C13—H13 | 120.9 |
| N1—C1—S1 | 119.0 (3) | C14—C13—H13 | 120.9 |
| C8—C1—S1 | 117.3 (3) | C13—C14—C15 | 121.0 (4) |
| C3—C2—N1 | 121.1 (3) | C13—C14—H14 | 119.5 |
| C3—C2—C10 | 123.1 (3) | C15—C14—H14 | 119.5 |
| N1—C2—C10 | 115.8 (3) | C10—C15—C14 | 121.3 (4) |
| C2—C3—C9 | 121.2 (3) | C10—C15—H15 | 119.4 |
| C2—C3—H3 | 119.4 | C14—C15—H15 | 119.4 |
| C9—C3—H3 | 119.4 | C17—C16—S1 | 116.5 (2) |
| C5—C4—C9 | 121.1 (4) | C17—C16—H16A | 108.2 |
| C5—C4—H4 | 119.4 | S1—C16—H16A | 108.2 |
| C9—C4—H4 | 119.4 | C17—C16—H16B | 108.2 |
| C4—C5—C6 | 120.3 (4) | S1—C16—H16B | 108.2 |
| C4—C5—H5 | 119.9 | H16A—C16—H16B | 107.3 |
| C6—C5—H5 | 119.9 | O1—C17—C18 | 121.2 (3) |
| C7—C6—C5 | 120.5 (4) | O1—C17—C16 | 122.2 (3) |
| C7—C6—H6 | 119.8 | C18—C17—C16 | 116.6 (3) |
| C5—C6—H6 | 119.8 | C23—C18—C19 | 118.6 (4) |
| C6—C7—C8 | 120.6 (4) | C23—C18—C17 | 118.9 (4) |
| C6—C7—H7 | 119.7 | C19—C18—C17 | 122.5 (3) |
| C8—C7—H7 | 119.7 | C20—C19—C18 | 120.7 (4) |
| C7—C8—C9 | 119.6 (3) | C20—C19—H19 | 119.6 |
| C7—C8—C1 | 123.8 (3) | C18—C19—H19 | 119.6 |
| C9—C8—C1 | 116.5 (3) | C21—C20—C19 | 119.6 (4) |
| C3—C9—C4 | 123.8 (3) | C21—C20—H20 | 120.2 |
| C3—C9—C8 | 118.2 (3) | C19—C20—H20 | 120.2 |
| C4—C9—C8 | 118.0 (3) | C20—C21—C22 | 120.6 (4) |
| C15—C10—C11 | 116.9 (4) | C20—C21—Cl1 | 120.1 (4) |
| C15—C10—C2 | 121.4 (3) | C22—C21—Cl1 | 119.3 (4) |
| C11—C10—C2 | 121.8 (3) | C23—C22—C21 | 119.7 (4) |
| C12—C11—C10 | 121.3 (4) | C23—C22—H22 | 120.2 |
| C12—C11—H11 | 119.3 | C21—C22—H22 | 120.2 |
| C10—C11—H11 | 119.3 | C22—C23—C18 | 120.8 (4) |
| C13—C12—C11 | 121.3 (4) | C22—C23—H23 | 119.6 |
| C13—C12—H12 | 119.4 | C18—C23—H23 | 119.6 |
| C2—N1—C1—C8 | −0.6 (4) | C3—C2—C10—C11 | −12.3 (5) |
| C2—N1—C1—S1 | 176.3 (2) | N1—C2—C10—C11 | 165.9 (3) |
| C16—S1—C1—N1 | 14.4 (3) | C15—C10—C11—C12 | −0.4 (6) |
| C16—S1—C1—C8 | −168.5 (2) | C2—C10—C11—C12 | −178.8 (4) |
| C1—N1—C2—C3 | −1.8 (4) | C10—C11—C12—C13 | 0.4 (7) |
| C1—N1—C2—C10 | 179.9 (3) | C11—C12—C13—C14 | 0.3 (7) |
| N1—C2—C3—C9 | 1.8 (5) | C12—C13—C14—C15 | −1.0 (7) |
| C10—C2—C3—C9 | 180.0 (3) | C11—C10—C15—C14 | −0.3 (6) |
| C9—C4—C5—C6 | 1.0 (6) | C2—C10—C15—C14 | 178.1 (3) |
| C4—C5—C6—C7 | −0.8 (6) | C13—C14—C15—C10 | 1.0 (6) |
| C5—C6—C7—C8 | −0.3 (6) | C1—S1—C16—C17 | −73.9 (3) |
| C6—C7—C8—C9 | 1.2 (5) | S1—C16—C17—O1 | −18.5 (4) |
| C6—C7—C8—C1 | −176.9 (3) | S1—C16—C17—C18 | 163.1 (2) |
| N1—C1—C8—C7 | −178.9 (3) | O1—C17—C18—C23 | 13.8 (5) |
| S1—C1—C8—C7 | 4.2 (4) | C16—C17—C18—C23 | −167.7 (3) |
| N1—C1—C8—C9 | 2.9 (5) | O1—C17—C18—C19 | −165.7 (3) |
| S1—C1—C8—C9 | −174.0 (2) | C16—C17—C18—C19 | 12.8 (4) |
| C2—C3—C9—C4 | −179.5 (3) | C23—C18—C19—C20 | −0.8 (5) |
| C2—C3—C9—C8 | 0.7 (5) | C17—C18—C19—C20 | 178.7 (3) |
| C5—C4—C9—C3 | −180.0 (3) | C18—C19—C20—C21 | 1.0 (6) |
| C5—C4—C9—C8 | −0.2 (5) | C19—C20—C21—C22 | −0.5 (6) |
| C7—C8—C9—C3 | 178.9 (3) | C19—C20—C21—Cl1 | −179.4 (3) |
| C1—C8—C9—C3 | −2.8 (4) | C20—C21—C22—C23 | −0.2 (6) |
| C7—C8—C9—C4 | −0.9 (4) | Cl1—C21—C22—C23 | 178.7 (3) |
| C1—C8—C9—C4 | 177.3 (3) | C21—C22—C23—C18 | 0.4 (6) |
| C3—C2—C10—C15 | 169.4 (3) | C19—C18—C23—C22 | 0.1 (5) |
| N1—C2—C10—C15 | −12.4 (4) | C17—C18—C23—C22 | −179.4 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···O1i | 0.93 | 2.51 | 3.322 (4) | 147 |
| C16—H16B···O1ii | 0.97 | 2.47 | 3.128 (4) | 125 |
| Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−1/2, −y+1/2, −z. |
We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.
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Organic thioethers are useful synthetic intermediates, key reagents in organic synthesis, bio-organic, medicinal, and heterocyclic chemistry (Cremlyn, 1996 and McReynolds et al., 2004). They are also useful as heteroatomic functional groups in organic synthesis, for example, chiral sulphoxides can be generated by the oxidation of thioethers which are useful as auxiliaries in asymmetric syntheses (Carreno, 1995). Many syntheses have been reported for the preparation of thioethers in literature (Kondo et al., 2000) whereas commonly used method is the alkylation of thiols (Mosberg et al., 1985 and references there in).
The compound (I) forms the dihedral angles of 11.73 (1)° and 66.07 (1)° between mean plane of isoquinoline moiety and phenyl ring and mean plane of isoquinoline moiety and chlorophenyl ring respectively. The crystal packing is stabilized by C—H···O inter molecular Hydrogen bonds (Figure 2).