Acta Cryst. (2010). E66, o1094 [ doi:10.1107/S1600536810013668 ]
In the title molecule, C22H14ClN3, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of 0.062 (1) Å for the triazole ring C atom, bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.02 (6) and 62.16 (6)°, respectively, to the mean plane of the triazoloisoquinoline ring system. The molecule is stabilized by a weak intramolecular ![[pi]](/logos/entities/pi_rmgif.gif)
- interaction [centroid-centroid distance = 3.7089 (10) Å] between the benzene and phenyl rings. In the crystal structure, weak intermolecular C-H
N hydrogen bonds and C-H interactions link the molecules.
2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with, 4-chlorobenzaldehyde (1.1 mmol) under refluxing conditions in isopropanol (10 ml) solvent to give the corresponding hydrazone in high yield. After removal of the solvent the compound was then oxidatively cyclized in nitrobenzene (10 ml) at 473 K. The product was recrystallized from dichlomethane to give block-shaped crystals.
H atoms were placed at calculated positions with C–H = 0.93 Å and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./bg2341fig1thm.gif)
| Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. |
![[Figure 2]](./bg2341fig2thm.gif)
| Fig. 2. A generel view of the packing diagram and the hydrogen bonding of (I). H atoms not involved in the motif shown have been omitted for clarity. |
| C22H14ClN3 | F(000) = 736 |
| Mr = 355.81 | Dx = 1.363 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 953 reflections |
| a = 7.9841 (3) Å | θ = 1.7–20.4° |
| b = 9.0679 (4) Å | µ = 0.23 mm−1 |
| c = 23.9881 (11) Å | T = 290 K |
| β = 93.078 (4)° | Block, colourless |
| V = 1734.20 (13) Å3 | 0.40 × 0.32 × 0.25 mm |
| Z = 4 |
| Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 3216 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 2090 reflections with I > 2σ(I) |
| graphite | Rint = 0.042 |
| ω scans | θmax = 25.5°, θmin = 3.0° |
| Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | h = −9→9 |
| Tmin = 0.902, Tmax = 0.945 | k = −10→10 |
| 19413 measured reflections | l = −29→29 |
| 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 0.97 | w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3 |
| 3216 reflections | (Δ/σ)max < 0.001 |
| 235 parameters | Δρmax = 0.11 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C22H14ClN3 | V = 1734.20 (13) Å3 |
| Mr = 355.81 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.9841 (3) Å | µ = 0.23 mm−1 |
| b = 9.0679 (4) Å | T = 290 K |
| c = 23.9881 (11) Å | 0.40 × 0.32 × 0.25 mm |
| β = 93.078 (4)° |
| Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 3216 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | 2090 reflections with I > 2σ(I) |
| Tmin = 0.902, Tmax = 0.945 | Rint = 0.042 |
| 19413 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.097 | Δρmax = 0.11 e Å−3 |
| S = 0.97 | Δρmin = −0.20 e Å−3 |
| 3216 reflections | Absolute structure: ? |
| 235 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.31231 (8) | 0.36657 (7) | 0.47872 (2) | 0.0881 (2) | |
| N1 | 0.59862 (15) | 0.38872 (12) | 0.21077 (5) | 0.0397 (3) | |
| C9 | 0.76959 (18) | 0.38731 (15) | 0.23083 (7) | 0.0420 (4) | |
| C7 | 0.84736 (19) | 0.37494 (16) | 0.13340 (7) | 0.0438 (4) | |
| C8 | 0.8862 (2) | 0.37965 (16) | 0.19258 (7) | 0.0465 (4) | |
| H8 | 0.9984 | 0.3773 | 0.2051 | 0.056* | |
| C2 | 0.67799 (19) | 0.38170 (16) | 0.11339 (7) | 0.0428 (4) | |
| C1 | 0.55381 (19) | 0.39096 (16) | 0.15404 (7) | 0.0421 (4) | |
| C10 | 0.81034 (19) | 0.39579 (17) | 0.29162 (7) | 0.0434 (4) | |
| C17 | 0.41623 (19) | 0.38678 (16) | 0.29626 (7) | 0.0438 (4) | |
| C16 | 0.44668 (19) | 0.39497 (16) | 0.23649 (7) | 0.0435 (4) | |
| N2 | 0.38951 (16) | 0.40120 (14) | 0.14584 (6) | 0.0515 (4) | |
| N3 | 0.32375 (16) | 0.40415 (15) | 0.19789 (6) | 0.0514 (4) | |
| C6 | 0.9712 (2) | 0.36397 (18) | 0.09438 (8) | 0.0555 (5) | |
| H6 | 1.0837 | 0.3616 | 0.1066 | 0.067* | |
| C20 | 0.3518 (2) | 0.3739 (2) | 0.40853 (7) | 0.0543 (5) | |
| C18 | 0.4740 (2) | 0.26909 (18) | 0.32926 (7) | 0.0484 (4) | |
| H18 | 0.5349 | 0.1940 | 0.3133 | 0.058* | |
| C3 | 0.6365 (2) | 0.37670 (19) | 0.05624 (8) | 0.0577 (5) | |
| H3 | 0.5248 | 0.3823 | 0.0432 | 0.069* | |
| C19 | 0.4425 (2) | 0.26216 (19) | 0.38509 (7) | 0.0536 (5) | |
| H19 | 0.4819 | 0.1832 | 0.4068 | 0.064* | |
| C21 | 0.2899 (2) | 0.4902 (2) | 0.37646 (8) | 0.0608 (5) | |
| H21 | 0.2271 | 0.5640 | 0.3923 | 0.073* | |
| C5 | 0.9281 (2) | 0.3568 (2) | 0.03855 (8) | 0.0668 (5) | |
| H5 | 1.0115 | 0.3473 | 0.0132 | 0.080* | |
| C11 | 0.7686 (2) | 0.51875 (18) | 0.32226 (7) | 0.0519 (4) | |
| H11 | 0.7176 | 0.5991 | 0.3042 | 0.062* | |
| C22 | 0.3224 (2) | 0.49554 (19) | 0.32059 (8) | 0.0541 (5) | |
| H22 | 0.2806 | 0.5735 | 0.2989 | 0.065* | |
| C15 | 0.8920 (2) | 0.27925 (19) | 0.31932 (7) | 0.0552 (5) | |
| H15 | 0.9245 | 0.1971 | 0.2993 | 0.066* | |
| C12 | 0.8017 (2) | 0.5234 (2) | 0.37932 (8) | 0.0627 (5) | |
| H12 | 0.7719 | 0.6062 | 0.3994 | 0.075* | |
| C4 | 0.7606 (3) | 0.3635 (2) | 0.01925 (8) | 0.0705 (6) | |
| H4 | 0.7329 | 0.3591 | −0.0189 | 0.085* | |
| C14 | 0.9250 (2) | 0.2852 (2) | 0.37642 (8) | 0.0679 (6) | |
| H14 | 0.9791 | 0.2067 | 0.3947 | 0.081* | |
| C13 | 0.8784 (3) | 0.4062 (2) | 0.40646 (8) | 0.0692 (6) | |
| H13 | 0.8988 | 0.4086 | 0.4450 | 0.083* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0944 (4) | 0.1095 (5) | 0.0616 (4) | 0.0059 (3) | 0.0163 (3) | 0.0034 (3) |
| N1 | 0.0311 (7) | 0.0376 (8) | 0.0498 (8) | 0.0006 (5) | −0.0026 (6) | −0.0017 (6) |
| C9 | 0.0333 (8) | 0.0365 (9) | 0.0552 (11) | −0.0003 (7) | −0.0060 (8) | −0.0025 (7) |
| C7 | 0.0389 (9) | 0.0396 (10) | 0.0527 (11) | −0.0010 (7) | −0.0007 (8) | −0.0034 (8) |
| C8 | 0.0324 (8) | 0.0480 (10) | 0.0579 (11) | 0.0006 (7) | −0.0081 (8) | −0.0035 (8) |
| C2 | 0.0394 (9) | 0.0379 (10) | 0.0506 (11) | 0.0012 (7) | −0.0031 (8) | −0.0051 (8) |
| C1 | 0.0369 (9) | 0.0377 (10) | 0.0507 (11) | 0.0006 (7) | −0.0077 (8) | −0.0028 (7) |
| C10 | 0.0359 (8) | 0.0429 (10) | 0.0505 (10) | −0.0047 (7) | −0.0054 (7) | −0.0001 (8) |
| C17 | 0.0349 (8) | 0.0376 (10) | 0.0590 (11) | −0.0045 (7) | 0.0047 (8) | 0.0024 (8) |
| C16 | 0.0346 (8) | 0.0368 (10) | 0.0589 (11) | −0.0023 (7) | 0.0011 (8) | 0.0003 (8) |
| N2 | 0.0355 (8) | 0.0589 (10) | 0.0593 (10) | −0.0008 (6) | −0.0046 (7) | −0.0029 (7) |
| N3 | 0.0361 (7) | 0.0562 (9) | 0.0614 (10) | −0.0033 (6) | −0.0009 (7) | 0.0018 (7) |
| C6 | 0.0410 (9) | 0.0599 (12) | 0.0654 (13) | 0.0036 (8) | 0.0017 (9) | −0.0061 (9) |
| C20 | 0.0513 (10) | 0.0557 (12) | 0.0565 (12) | −0.0062 (9) | 0.0074 (9) | 0.0003 (9) |
| C18 | 0.0453 (10) | 0.0369 (10) | 0.0634 (12) | 0.0004 (7) | 0.0058 (8) | −0.0005 (9) |
| C3 | 0.0483 (10) | 0.0688 (13) | 0.0549 (12) | 0.0052 (9) | −0.0065 (9) | −0.0086 (9) |
| C19 | 0.0523 (11) | 0.0455 (11) | 0.0629 (12) | −0.0016 (8) | 0.0012 (9) | 0.0083 (9) |
| C21 | 0.0576 (11) | 0.0516 (12) | 0.0750 (14) | 0.0062 (9) | 0.0187 (10) | 0.0001 (10) |
| C5 | 0.0571 (12) | 0.0837 (14) | 0.0604 (13) | 0.0074 (10) | 0.0111 (10) | −0.0074 (11) |
| C11 | 0.0538 (11) | 0.0430 (10) | 0.0582 (12) | −0.0032 (8) | −0.0030 (9) | −0.0006 (9) |
| C22 | 0.0489 (10) | 0.0447 (11) | 0.0695 (13) | 0.0059 (8) | 0.0103 (9) | 0.0087 (9) |
| C15 | 0.0503 (11) | 0.0506 (11) | 0.0636 (12) | 0.0043 (8) | −0.0075 (9) | 0.0006 (9) |
| C12 | 0.0687 (12) | 0.0608 (13) | 0.0586 (13) | −0.0125 (10) | 0.0018 (10) | −0.0137 (10) |
| C4 | 0.0704 (14) | 0.0933 (16) | 0.0473 (11) | 0.0114 (11) | −0.0019 (10) | −0.0106 (10) |
| C14 | 0.0628 (12) | 0.0744 (14) | 0.0644 (14) | 0.0050 (11) | −0.0154 (10) | 0.0145 (11) |
| C13 | 0.0693 (13) | 0.0853 (17) | 0.0517 (12) | −0.0141 (12) | −0.0087 (10) | 0.0011 (12) |
| Cl1—C20 | 1.7307 (18) | C20—C21 | 1.381 (2) |
| N1—C1 | 1.3886 (19) | C20—C19 | 1.383 (2) |
| N1—C16 | 1.3913 (19) | C18—C19 | 1.377 (2) |
| N1—C9 | 1.4228 (18) | C18—H18 | 0.9300 |
| C9—C8 | 1.343 (2) | C3—C4 | 1.371 (3) |
| C9—C10 | 1.479 (2) | C3—H3 | 0.9300 |
| C7—C6 | 1.401 (2) | C19—H19 | 0.9300 |
| C7—C2 | 1.412 (2) | C21—C22 | 1.380 (2) |
| C7—C8 | 1.437 (2) | C21—H21 | 0.9300 |
| C8—H8 | 0.9300 | C5—C4 | 1.393 (3) |
| C2—C3 | 1.394 (2) | C5—H5 | 0.9300 |
| C2—C1 | 1.430 (2) | C11—C12 | 1.381 (2) |
| C1—N2 | 1.3193 (19) | C11—H11 | 0.9300 |
| C10—C11 | 1.386 (2) | C22—H22 | 0.9300 |
| C10—C15 | 1.392 (2) | C15—C14 | 1.382 (2) |
| C17—C22 | 1.386 (2) | C15—H15 | 0.9300 |
| C17—C18 | 1.393 (2) | C12—C13 | 1.374 (3) |
| C17—C16 | 1.469 (2) | C12—H12 | 0.9300 |
| C16—N3 | 1.315 (2) | C4—H4 | 0.9300 |
| N2—N3 | 1.3804 (19) | C14—C13 | 1.375 (3) |
| C6—C5 | 1.366 (2) | C14—H14 | 0.9300 |
| C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| C1—N1—C16 | 104.42 (12) | C19—C18—H18 | 119.5 |
| C1—N1—C9 | 121.57 (13) | C17—C18—H18 | 119.5 |
| C16—N1—C9 | 133.95 (14) | C4—C3—C2 | 119.83 (17) |
| C8—C9—N1 | 117.18 (14) | C4—C3—H3 | 120.1 |
| C8—C9—C10 | 123.53 (14) | C2—C3—H3 | 120.1 |
| N1—C9—C10 | 119.28 (14) | C18—C19—C20 | 119.27 (16) |
| C6—C7—C2 | 118.25 (15) | C18—C19—H19 | 120.4 |
| C6—C7—C8 | 122.66 (15) | C20—C19—H19 | 120.4 |
| C2—C7—C8 | 119.09 (15) | C22—C21—C20 | 119.20 (17) |
| C9—C8—C7 | 123.76 (14) | C22—C21—H21 | 120.4 |
| C9—C8—H8 | 118.1 | C20—C21—H21 | 120.4 |
| C7—C8—H8 | 118.1 | C6—C5—C4 | 120.67 (18) |
| C3—C2—C7 | 120.39 (16) | C6—C5—H5 | 119.7 |
| C3—C2—C1 | 122.38 (14) | C4—C5—H5 | 119.7 |
| C7—C2—C1 | 117.21 (14) | C12—C11—C10 | 120.77 (16) |
| N2—C1—N1 | 110.42 (15) | C12—C11—H11 | 119.6 |
| N2—C1—C2 | 128.52 (15) | C10—C11—H11 | 119.6 |
| N1—C1—C2 | 121.06 (13) | C21—C22—C17 | 121.20 (16) |
| C11—C10—C15 | 118.54 (15) | C21—C22—H22 | 119.4 |
| C11—C10—C9 | 121.21 (14) | C17—C22—H22 | 119.4 |
| C15—C10—C9 | 120.25 (14) | C14—C15—C10 | 120.20 (17) |
| C22—C17—C18 | 118.43 (16) | C14—C15—H15 | 119.9 |
| C22—C17—C16 | 119.77 (15) | C10—C15—H15 | 119.9 |
| C18—C17—C16 | 121.76 (15) | C13—C12—C11 | 120.20 (18) |
| N3—C16—N1 | 109.02 (14) | C13—C12—H12 | 119.9 |
| N3—C16—C17 | 122.28 (14) | C11—C12—H12 | 119.9 |
| N1—C16—C17 | 128.65 (14) | C3—C4—C5 | 120.23 (18) |
| C1—N2—N3 | 106.85 (13) | C3—C4—H4 | 119.9 |
| C16—N3—N2 | 109.26 (13) | C5—C4—H4 | 119.9 |
| C5—C6—C7 | 120.60 (16) | C13—C14—C15 | 120.54 (17) |
| C5—C6—H6 | 119.7 | C13—C14—H14 | 119.7 |
| C7—C6—H6 | 119.7 | C15—C14—H14 | 119.7 |
| C21—C20—C19 | 120.84 (17) | C12—C13—C14 | 119.70 (18) |
| C21—C20—Cl1 | 119.56 (15) | C12—C13—H13 | 120.2 |
| C19—C20—Cl1 | 119.60 (14) | C14—C13—H13 | 120.2 |
| C19—C18—C17 | 121.02 (16) | ||
| C1—N1—C9—C8 | −3.74 (19) | C18—C17—C16—N1 | −55.3 (2) |
| C16—N1—C9—C8 | 179.68 (14) | N1—C1—N2—N3 | −0.67 (16) |
| C1—N1—C9—C10 | 175.62 (12) | C2—C1—N2—N3 | 178.84 (14) |
| C16—N1—C9—C10 | −1.0 (2) | N1—C16—N3—N2 | 1.22 (16) |
| N1—C9—C8—C7 | 0.9 (2) | C17—C16—N3—N2 | −176.41 (12) |
| C10—C9—C8—C7 | −178.46 (13) | C1—N2—N3—C16 | −0.35 (16) |
| C6—C7—C8—C9 | −178.68 (15) | C2—C7—C6—C5 | −1.4 (2) |
| C2—C7—C8—C9 | 1.4 (2) | C8—C7—C6—C5 | 178.64 (15) |
| C6—C7—C2—C3 | 0.3 (2) | C22—C17—C18—C19 | −1.5 (2) |
| C8—C7—C2—C3 | −179.71 (13) | C16—C17—C18—C19 | −179.15 (14) |
| C6—C7—C2—C1 | 179.22 (14) | C7—C2—C3—C4 | 0.7 (2) |
| C8—C7—C2—C1 | −0.8 (2) | C1—C2—C3—C4 | −178.11 (16) |
| C16—N1—C1—N2 | 1.37 (15) | C17—C18—C19—C20 | 0.1 (2) |
| C9—N1—C1—N2 | −176.09 (12) | C21—C20—C19—C18 | 1.3 (3) |
| C16—N1—C1—C2 | −178.19 (13) | Cl1—C20—C19—C18 | −179.73 (12) |
| C9—N1—C1—C2 | 4.4 (2) | C19—C20—C21—C22 | −1.3 (3) |
| C3—C2—C1—N2 | −2.6 (2) | Cl1—C20—C21—C22 | 179.77 (13) |
| C7—C2—C1—N2 | 178.59 (14) | C7—C6—C5—C4 | 1.5 (3) |
| C3—C2—C1—N1 | 176.91 (13) | C15—C10—C11—C12 | −2.3 (2) |
| C7—C2—C1—N1 | −1.9 (2) | C9—C10—C11—C12 | 177.63 (15) |
| C8—C9—C10—C11 | 116.02 (18) | C20—C21—C22—C17 | −0.2 (3) |
| N1—C9—C10—C11 | −63.30 (19) | C18—C17—C22—C21 | 1.6 (2) |
| C8—C9—C10—C15 | −64.0 (2) | C16—C17—C22—C21 | 179.24 (15) |
| N1—C9—C10—C15 | 116.67 (16) | C11—C10—C15—C14 | 2.2 (2) |
| C1—N1—C16—N3 | −1.56 (15) | C9—C10—C15—C14 | −177.82 (15) |
| C9—N1—C16—N3 | 175.42 (14) | C10—C11—C12—C13 | 0.7 (3) |
| C1—N1—C16—C17 | 175.88 (14) | C2—C3—C4—C5 | −0.7 (3) |
| C9—N1—C16—C17 | −7.1 (2) | C6—C5—C4—C3 | −0.4 (3) |
| C22—C17—C16—N3 | −55.7 (2) | C10—C15—C14—C13 | −0.3 (3) |
| C18—C17—C16—N3 | 121.87 (17) | C11—C12—C13—C14 | 1.2 (3) |
| C22—C17—C16—N1 | 127.15 (17) | C15—C14—C13—C12 | −1.4 (3) |
| Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C16, N1/C1/C2/C7–C9 and C2–C7 rings, respectively. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6···N2i | 0.93 | 2.59 | 3.514 (2) | 170 |
| C8—H8···N3i | 0.93 | 2.62 | 3.496 (2) | 156 |
| C18—H18···Cg1ii | 0.93 | 2.70 | 3.4524 (17) | 138 |
| C21—H21···Cg3iii | 0.93 | 2.89 | 3.7139 (19) | 149 |
| C22—H22···Cg2iii | 0.93 | 2.90 | 3.5442 (18) | 128 |
| Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
| Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C16, N1/C1/C2/C7–C9 and C2–C7 rings, respectively. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6···N2i | 0.93 | 2.59 | 3.514 (2) | 170 |
| C8—H8···N3i | 0.93 | 2.62 | 3.496 (2) | 156 |
| C18—H18···Cg1ii | 0.93 | 2.70 | 3.4524 (17) | 138 |
| C21—H21···Cg3iii | 0.93 | 2.89 | 3.7139 (19) | 149 |
| C22—H22···Cg2iii | 0.93 | 2.90 | 3.5442 (18) | 128 |
| Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
We thank the FIST program for the data collection at SSCU, IISc, Bangalore. We also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.
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As part of our search for new isoquinoline analogues, we focused on the synthesis of the titled compound, which crystal structure is reported.
In the title molecule (I), Fig. 1, the triazoloisoquinoline ring system (N1–N3/C1–C9/C16) is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of -0.062 (1) Å for the triazole ring C16 atom, bonded to the benzene ring (C17–C22). The benzene (C17–C22) and phenyl (C10–C15) rings are twisted by 57.02 (6) and 62.16 (6) ° with respect to the mean plane of the triazoloisoquinoline ring system. The dihedral angle betwen the benzene (C17–C22) and phenyl (C10–C15) rings is 22.21 (8)° .
The molecule is stabilized by a weak intramolecular π-π interaction [Cg4···Cg5(x, y, z) = 3.7089 (10) Å; Cg4 and Cg5 are the centroids of the rings C10–C15 and C17–C22, respectively]. In the crystal structure, weak intermolecular C—H···N hydrogen bonds and C—H···π interactions (Table 1, Fig. 2) link the molecules to each other.