Acta Cryst. (2010). E66, o1081 [ doi:10.1107/S1600536810013012 ]
In the title molecule, C23H14N4, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.038 (2) Å and a maximum deviation of -0.030 (2) Å from the mean plane of the triazole ring C atom which is bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.65 (8) and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, molecules are linked by weak aromatic ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions [centroid-centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical intermolecular C-H
N hydrogen bond.
2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with 4-formylbenzonitrile (1.1 mmol) under refluxing conditions isopropanol (10 ml) solvent to give the corresponding hydrazone in high yield. After removal of 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.
All H atoms were placed in calculated positions with C–H = 0.93Å and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C).
Pure diffraction experiment (ratio observed/unique reflections 47%) we explain by weak diffraction of the crystal.
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]](./rk2199fig1thm.gif)
| Fig. 1. The view of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. |
![[Figure 2]](./rk2199fig2thm.gif)
| Fig. 2. The packing diagram and the hydrogen bonding in the title crystal structure viewed down the [1 0 0] direction. H atoms not involved in the motif shown have been omitted for clarity. |
| C23H14N4 | F(000) = 1440 |
| Mr = 346.38 | Dx = 1.345 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 1235 reflections |
| a = 7.1614 (3) Å | θ = 1.6–20.4° |
| b = 18.0957 (7) Å | µ = 0.08 mm−1 |
| c = 26.4021 (9) Å | T = 290 K |
| V = 3421.5 (2) Å3 | Block, colourless |
| Z = 8 | 0.25 × 0.21 × 0.17 mm |
| Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 3164 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 1490 reflections with I > 2σ(I) |
| graphite | Rint = 0.070 |
| ω scans | θmax = 25.5°, θmin = 3.1° |
| Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | h = −8→7 |
| Tmin = 0.959, Tmax = 0.986 | k = −21→21 |
| 14977 measured reflections | l = −31→31 |
| 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.100 | H-atom parameters constrained |
| S = 0.81 | w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3 |
| 3164 reflections | (Δ/σ)max < 0.001 |
| 244 parameters | Δρmax = 0.15 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C23H14N4 | V = 3421.5 (2) Å3 |
| Mr = 346.38 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 7.1614 (3) Å | µ = 0.08 mm−1 |
| b = 18.0957 (7) Å | T = 290 K |
| c = 26.4021 (9) Å | 0.25 × 0.21 × 0.17 mm |
| Oxford Xcalibur Eos (Nova) CCD detector diffractometer | 3164 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) | 1490 reflections with I > 2σ(I) |
| Tmin = 0.959, Tmax = 0.986 | Rint = 0.070 |
| 14977 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.100 | Δρmax = 0.15 e Å−3 |
| S = 0.81 | Δρmin = −0.20 e Å−3 |
| 3164 reflections | Absolute structure: ? |
| 244 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | ||
| N1 | 0.6627 (2) | 0.33099 (9) | 0.03366 (6) | 0.0370 (4) | |
| N2 | 0.5820 (3) | 0.22467 (10) | −0.00072 (7) | 0.0510 (5) | |
| N3 | 0.6063 (2) | 0.27481 (11) | −0.03950 (7) | 0.0495 (5) | |
| N4 | 0.5390 (3) | 0.08980 (15) | 0.27259 (9) | 0.0927 (9) | |
| C1 | 0.6539 (3) | 0.33812 (13) | −0.01851 (8) | 0.0395 (5) | |
| C2 | 0.6915 (3) | 0.40722 (12) | −0.04237 (8) | 0.0407 (6) | |
| C3 | 0.6888 (3) | 0.41638 (14) | −0.09495 (8) | 0.0490 (6) | |
| H3 | 0.6586 | 0.3766 | −0.1157 | 0.059* | |
| C4 | 0.7302 (3) | 0.48368 (15) | −0.11611 (9) | 0.0570 (7) | |
| H4 | 0.7297 | 0.4894 | −0.1511 | 0.068* | |
| C5 | 0.7728 (3) | 0.54308 (14) | −0.08507 (9) | 0.0581 (7) | |
| H5 | 0.8002 | 0.5887 | −0.0996 | 0.070* | |
| C6 | 0.7754 (3) | 0.53585 (13) | −0.03328 (9) | 0.0526 (6) | |
| H6 | 0.8030 | 0.5764 | −0.0130 | 0.063* | |
| C7 | 0.7364 (3) | 0.46741 (12) | −0.01110 (8) | 0.0416 (6) | |
| C8 | 0.7527 (3) | 0.45523 (12) | 0.04249 (8) | 0.0454 (6) | |
| H8 | 0.7853 | 0.4952 | 0.0628 | 0.054* | |
| C9 | 0.7238 (3) | 0.38972 (12) | 0.06498 (8) | 0.0387 (6) | |
| C10 | 0.7671 (3) | 0.37673 (11) | 0.11909 (8) | 0.0374 (5) | |
| C11 | 0.8907 (3) | 0.32192 (12) | 0.13406 (8) | 0.0456 (6) | |
| H11 | 0.9426 | 0.2903 | 0.1101 | 0.055* | |
| C12 | 0.9365 (3) | 0.31454 (14) | 0.18466 (9) | 0.0562 (7) | |
| H12 | 1.0180 | 0.2774 | 0.1948 | 0.067* | |
| C13 | 0.8625 (4) | 0.36161 (15) | 0.22007 (9) | 0.0645 (8) | |
| H13 | 0.8935 | 0.3561 | 0.2541 | 0.077* | |
| C14 | 0.7438 (4) | 0.41647 (15) | 0.20553 (9) | 0.0595 (7) | |
| H14 | 0.6960 | 0.4490 | 0.2295 | 0.071* | |
| C15 | 0.6944 (3) | 0.42380 (13) | 0.15537 (9) | 0.0478 (6) | |
| H15 | 0.6114 | 0.4608 | 0.1458 | 0.057* | |
| C16 | 0.6137 (3) | 0.25837 (12) | 0.04252 (8) | 0.0406 (6) | |
| C17 | 0.5906 (3) | 0.22246 (12) | 0.09194 (8) | 0.0403 (5) | |
| C18 | 0.6918 (3) | 0.15870 (13) | 0.10218 (8) | 0.0480 (6) | |
| H18 | 0.7701 | 0.1391 | 0.0775 | 0.058* | |
| C19 | 0.6771 (3) | 0.12414 (12) | 0.14857 (9) | 0.0523 (6) | |
| H19 | 0.7474 | 0.0821 | 0.1554 | 0.063* | |
| C20 | 0.5575 (3) | 0.15217 (13) | 0.18497 (8) | 0.0480 (6) | |
| C21 | 0.4514 (3) | 0.21414 (13) | 0.17476 (8) | 0.0524 (6) | |
| H21 | 0.3693 | 0.2324 | 0.1990 | 0.063* | |
| C22 | 0.4678 (3) | 0.24882 (13) | 0.12834 (8) | 0.0503 (6) | |
| H22 | 0.3957 | 0.2903 | 0.1214 | 0.060* | |
| C23 | 0.5459 (3) | 0.11720 (15) | 0.23405 (10) | 0.0629 (8) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0393 (10) | 0.0337 (11) | 0.0381 (11) | −0.0026 (8) | −0.0031 (8) | −0.0012 (9) |
| N2 | 0.0631 (13) | 0.0439 (12) | 0.0459 (12) | −0.0068 (10) | −0.0062 (10) | −0.0041 (11) |
| N3 | 0.0614 (13) | 0.0457 (13) | 0.0414 (11) | −0.0057 (10) | −0.0054 (9) | 0.0003 (10) |
| N4 | 0.0964 (19) | 0.124 (2) | 0.0576 (16) | 0.0151 (16) | 0.0099 (14) | 0.0261 (16) |
| C1 | 0.0394 (14) | 0.0404 (15) | 0.0387 (13) | −0.0003 (11) | −0.0054 (10) | −0.0027 (12) |
| C2 | 0.0357 (13) | 0.0443 (15) | 0.0421 (14) | 0.0023 (11) | −0.0010 (10) | 0.0016 (12) |
| C3 | 0.0463 (15) | 0.0544 (17) | 0.0463 (15) | 0.0062 (13) | 0.0002 (11) | 0.0032 (13) |
| C4 | 0.0515 (17) | 0.0687 (19) | 0.0507 (15) | 0.0085 (14) | 0.0028 (12) | 0.0160 (15) |
| C5 | 0.0464 (16) | 0.0584 (19) | 0.0695 (19) | −0.0011 (13) | −0.0002 (13) | 0.0241 (15) |
| C6 | 0.0500 (15) | 0.0465 (16) | 0.0613 (17) | −0.0003 (12) | −0.0016 (13) | 0.0076 (13) |
| C7 | 0.0344 (14) | 0.0413 (15) | 0.0490 (14) | 0.0004 (11) | −0.0046 (11) | 0.0072 (12) |
| C8 | 0.0461 (14) | 0.0387 (15) | 0.0513 (15) | −0.0011 (11) | −0.0052 (12) | −0.0054 (12) |
| C9 | 0.0347 (14) | 0.0368 (15) | 0.0445 (13) | −0.0002 (10) | −0.0019 (11) | −0.0060 (11) |
| C10 | 0.0399 (14) | 0.0336 (13) | 0.0386 (13) | −0.0029 (11) | −0.0012 (10) | −0.0018 (11) |
| C11 | 0.0441 (14) | 0.0436 (15) | 0.0492 (15) | −0.0011 (12) | −0.0005 (11) | −0.0047 (12) |
| C12 | 0.0519 (16) | 0.0604 (18) | 0.0563 (17) | 0.0036 (13) | −0.0129 (13) | 0.0072 (15) |
| C13 | 0.075 (2) | 0.077 (2) | 0.0416 (15) | −0.0091 (16) | −0.0111 (14) | 0.0000 (15) |
| C14 | 0.0721 (18) | 0.0580 (18) | 0.0483 (16) | −0.0068 (15) | 0.0073 (14) | −0.0115 (14) |
| C15 | 0.0507 (15) | 0.0429 (15) | 0.0497 (15) | 0.0013 (12) | 0.0008 (12) | −0.0051 (13) |
| C16 | 0.0436 (14) | 0.0361 (14) | 0.0423 (13) | −0.0039 (11) | −0.0025 (11) | −0.0031 (12) |
| C17 | 0.0400 (13) | 0.0351 (14) | 0.0458 (14) | −0.0048 (11) | −0.0039 (11) | −0.0015 (11) |
| C18 | 0.0586 (15) | 0.0392 (15) | 0.0463 (15) | 0.0034 (13) | 0.0039 (12) | −0.0031 (12) |
| C19 | 0.0637 (17) | 0.0400 (15) | 0.0532 (16) | 0.0085 (12) | 0.0004 (13) | 0.0023 (13) |
| C20 | 0.0498 (15) | 0.0497 (16) | 0.0446 (14) | −0.0053 (13) | −0.0014 (12) | 0.0051 (13) |
| C21 | 0.0516 (16) | 0.0559 (17) | 0.0497 (16) | 0.0024 (14) | 0.0067 (12) | −0.0002 (13) |
| C22 | 0.0516 (16) | 0.0417 (15) | 0.0575 (16) | 0.0052 (12) | −0.0014 (13) | 0.0000 (13) |
| C23 | 0.0591 (18) | 0.075 (2) | 0.0546 (18) | 0.0052 (14) | 0.0030 (14) | 0.0043 (16) |
| N1—C16 | 1.380 (2) | C10—C11 | 1.387 (3) |
| N1—C1 | 1.385 (2) | C11—C12 | 1.382 (3) |
| N1—C9 | 1.416 (2) | C11—H11 | 0.9300 |
| N2—C16 | 1.314 (2) | C12—C13 | 1.371 (3) |
| N2—N3 | 1.379 (2) | C12—H12 | 0.9300 |
| N3—C1 | 1.318 (3) | C13—C14 | 1.362 (3) |
| N4—C23 | 1.133 (3) | C13—H13 | 0.9300 |
| C1—C2 | 1.426 (3) | C14—C15 | 1.377 (3) |
| C2—C3 | 1.398 (3) | C14—H14 | 0.9300 |
| C2—C7 | 1.404 (3) | C15—H15 | 0.9300 |
| C3—C4 | 1.372 (3) | C16—C17 | 1.467 (3) |
| C3—H3 | 0.9300 | C17—C22 | 1.387 (3) |
| C4—C5 | 1.386 (3) | C17—C18 | 1.389 (3) |
| C4—H4 | 0.9300 | C18—C19 | 1.379 (3) |
| C5—C6 | 1.374 (3) | C18—H18 | 0.9300 |
| C5—H5 | 0.9300 | C19—C20 | 1.384 (3) |
| C6—C7 | 1.398 (3) | C19—H19 | 0.9300 |
| C6—H6 | 0.9300 | C20—C21 | 1.381 (3) |
| C7—C8 | 1.437 (3) | C20—C23 | 1.445 (3) |
| C8—C9 | 1.342 (3) | C21—C22 | 1.382 (3) |
| C8—H8 | 0.9300 | C21—H21 | 0.9300 |
| C9—C10 | 1.481 (3) | C22—H22 | 0.9300 |
| C10—C15 | 1.384 (3) | ||
| C16—N1—C1 | 104.23 (17) | C12—C11—H11 | 120.1 |
| C16—N1—C9 | 133.97 (18) | C10—C11—H11 | 120.1 |
| C1—N1—C9 | 121.67 (19) | C13—C12—C11 | 120.5 (2) |
| C16—N2—N3 | 108.54 (17) | C13—C12—H12 | 119.7 |
| C1—N3—N2 | 107.01 (17) | C11—C12—H12 | 119.7 |
| N3—C1—N1 | 110.4 (2) | C14—C13—C12 | 120.1 (2) |
| N3—C1—C2 | 128.7 (2) | C14—C13—H13 | 119.9 |
| N1—C1—C2 | 120.8 (2) | C12—C13—H13 | 119.9 |
| C3—C2—C7 | 119.7 (2) | C13—C14—C15 | 120.1 (2) |
| C3—C2—C1 | 122.7 (2) | C13—C14—H14 | 120.0 |
| C7—C2—C1 | 117.6 (2) | C15—C14—H14 | 120.0 |
| C4—C3—C2 | 120.4 (2) | C14—C15—C10 | 120.7 (2) |
| C4—C3—H3 | 119.8 | C14—C15—H15 | 119.7 |
| C2—C3—H3 | 119.8 | C10—C15—H15 | 119.7 |
| C3—C4—C5 | 119.7 (2) | N2—C16—N1 | 109.78 (18) |
| C3—C4—H4 | 120.2 | N2—C16—C17 | 123.23 (19) |
| C5—C4—H4 | 120.2 | N1—C16—C17 | 126.94 (19) |
| C6—C5—C4 | 121.2 (2) | C22—C17—C18 | 118.8 (2) |
| C6—C5—H5 | 119.4 | C22—C17—C16 | 122.4 (2) |
| C4—C5—H5 | 119.4 | C18—C17—C16 | 118.8 (2) |
| C5—C6—C7 | 119.9 (2) | C19—C18—C17 | 120.6 (2) |
| C5—C6—H6 | 120.0 | C19—C18—H18 | 119.7 |
| C7—C6—H6 | 120.0 | C17—C18—H18 | 119.7 |
| C6—C7—C2 | 119.1 (2) | C18—C19—C20 | 119.9 (2) |
| C6—C7—C8 | 122.1 (2) | C18—C19—H19 | 120.1 |
| C2—C7—C8 | 118.6 (2) | C20—C19—H19 | 120.1 |
| C9—C8—C7 | 124.0 (2) | C21—C20—C19 | 120.2 (2) |
| C9—C8—H8 | 118.0 | C21—C20—C23 | 119.9 (2) |
| C7—C8—H8 | 118.0 | C19—C20—C23 | 119.9 (2) |
| C8—C9—N1 | 116.90 (19) | C20—C21—C22 | 119.7 (2) |
| C8—C9—C10 | 122.32 (19) | C20—C21—H21 | 120.2 |
| N1—C9—C10 | 120.61 (19) | C22—C21—H21 | 120.2 |
| C15—C10—C11 | 118.9 (2) | C21—C22—C17 | 120.8 (2) |
| C15—C10—C9 | 119.4 (2) | C21—C22—H22 | 119.6 |
| C11—C10—C9 | 121.49 (19) | C17—C22—H22 | 119.6 |
| C12—C11—C10 | 119.7 (2) | N4—C23—C20 | 179.2 (3) |
| C16—N2—N3—C1 | 0.5 (2) | N1—C9—C10—C15 | −131.8 (2) |
| N2—N3—C1—N1 | 0.3 (2) | C8—C9—C10—C11 | −121.8 (2) |
| N2—N3—C1—C2 | −178.9 (2) | N1—C9—C10—C11 | 53.2 (3) |
| C16—N1—C1—N3 | −0.9 (2) | C15—C10—C11—C12 | 1.0 (3) |
| C9—N1—C1—N3 | 175.46 (16) | C9—C10—C11—C12 | 176.0 (2) |
| C16—N1—C1—C2 | 178.40 (18) | C10—C11—C12—C13 | −0.9 (3) |
| C9—N1—C1—C2 | −5.2 (3) | C11—C12—C13—C14 | −0.4 (4) |
| N3—C1—C2—C3 | −2.5 (3) | C12—C13—C14—C15 | 1.4 (4) |
| N1—C1—C2—C3 | 178.35 (17) | C13—C14—C15—C10 | −1.3 (4) |
| N3—C1—C2—C7 | 178.8 (2) | C11—C10—C15—C14 | 0.0 (3) |
| N1—C1—C2—C7 | −0.4 (3) | C9—C10—C15—C14 | −175.0 (2) |
| C7—C2—C3—C4 | 0.2 (3) | N3—N2—C16—N1 | −1.0 (2) |
| C1—C2—C3—C4 | −178.5 (2) | N3—N2—C16—C17 | 176.63 (18) |
| C2—C3—C4—C5 | −0.8 (3) | C1—N1—C16—N2 | 1.2 (2) |
| C3—C4—C5—C6 | 0.4 (3) | C9—N1—C16—N2 | −174.51 (19) |
| C4—C5—C6—C7 | 0.7 (3) | C1—N1—C16—C17 | −176.38 (19) |
| C5—C6—C7—C2 | −1.2 (3) | C9—N1—C16—C17 | 7.9 (4) |
| C5—C6—C7—C8 | 174.57 (19) | N2—C16—C17—C22 | −120.5 (2) |
| C3—C2—C7—C6 | 0.8 (3) | N1—C16—C17—C22 | 56.7 (3) |
| C1—C2—C7—C6 | 179.55 (19) | N2—C16—C17—C18 | 57.8 (3) |
| C3—C2—C7—C8 | −175.16 (18) | N1—C16—C17—C18 | −125.0 (2) |
| C1—C2—C7—C8 | 3.6 (3) | C22—C17—C18—C19 | −3.0 (3) |
| C6—C7—C8—C9 | −177.2 (2) | C16—C17—C18—C19 | 178.6 (2) |
| C2—C7—C8—C9 | −1.5 (3) | C17—C18—C19—C20 | 1.4 (3) |
| C7—C8—C9—N1 | −3.9 (3) | C18—C19—C20—C21 | 0.7 (3) |
| C7—C8—C9—C10 | 171.32 (18) | C18—C19—C20—C23 | −178.3 (2) |
| C16—N1—C9—C8 | −177.6 (2) | C19—C20—C21—C22 | −1.2 (3) |
| C1—N1—C9—C8 | 7.3 (3) | C23—C20—C21—C22 | 177.8 (2) |
| C16—N1—C9—C10 | 7.0 (3) | C20—C21—C22—C17 | −0.4 (3) |
| C1—N1—C9—C10 | −168.06 (17) | C18—C17—C22—C21 | 2.5 (3) |
| C8—C9—C10—C15 | 53.1 (3) | C16—C17—C22—C21 | −179.2 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C11—H11···N3i | 0.93 | 2.50 | 3.418 (3) | 170 |
| Symmetry codes: (i) x+1/2, −y+1/2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C11—H11···N3i | 0.93 | 2.50 | 3.418 (3) | 170 |
| Symmetry codes: (i) x+1/2, −y+1/2, −z. |
The authors thank the FIST program for data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. The authors thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Ng, S. W. (2010). Acta Cryst. E66, o488.
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
As part of our search for new isoquinoline analogues (Khan et al., 2010), we focused on synthesis of titled compounds and the crystal structure is reported.
In the title molecule, Fig. 1, the triazoloisoquinoline ring system (N1-N3/C1-C9/C16) is nearly planar, with an r.m.s. deviation of 0.038 (2)Å and a maximum deviation of -0.030 (2)Å from the mean plane for the triazole ring C16 atom which is bonded to the benzene ring (C17-C22). The benzene (C17-C22) and phenyl (C10-C15) rings are twisted by 57.65 (8)° and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The benzene (C17-C22) and phenyl (C10-C15) rings make a dihedral angle of 29.10 (11)° with each other.
Molecular conformation is stabilized by a weak π–π interaction [Cg4···Cg5 = 3.8229 (14)Å, where are Cg4 and Cg5 are centroids of the C10-C15 and C17-C22 rings, respectively]. In the crystal structure, the molecules are linked by weak aromatic π–π interactions [Cg1···Cg1ii = 3.8074 (12)Å, symmetry code: (ii) x-1/2, 1/2-y, -z. Cg1 is the centroid of the N1-N3/C1/C16 ring]. In addition, the crystal structure exhibits an intermolecular non-classical C–H···N hydrogen bond (Table 1, Fig. 2).